WO2014018397A1 - Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxphenyl) pyridine-2-carboxylic acid or a derivative thereof and vlcfa synthesis and fatty acid/lipid synthesis inhibiting herbicides - Google Patents

Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxphenyl) pyridine-2-carboxylic acid or a derivative thereof and vlcfa synthesis and fatty acid/lipid synthesis inhibiting herbicides Download PDF

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Publication number
WO2014018397A1
WO2014018397A1 PCT/US2013/051302 US2013051302W WO2014018397A1 WO 2014018397 A1 WO2014018397 A1 WO 2014018397A1 US 2013051302 W US2013051302 W US 2013051302W WO 2014018397 A1 WO2014018397 A1 WO 2014018397A1
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WO
WIPO (PCT)
Prior art keywords
compound
ester
formula
gai
salt
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Ceased
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PCT/US2013/051302
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French (fr)
Inventor
Carla Yerkes
Richard Mann
Ikuo Shiraishi
Shingo Yanagiyama
Norbert Satchivi
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Corteva Agriscience LLC
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Dow AgroSciences LLC
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Publication date
Priority to AU2013293310A priority Critical patent/AU2013293310B2/en
Priority to ES13822431T priority patent/ES2717283T3/en
Priority to EP13822431.6A priority patent/EP2877008B1/en
Priority to CA2879989A priority patent/CA2879989A1/en
Priority to CN201380048742.5A priority patent/CN104640447B/en
Priority to HK15110412.2A priority patent/HK1209589A1/en
Priority to UAA201501448A priority patent/UA115990C2/en
Priority to MX2015001150A priority patent/MX2015001150A/en
Priority to JP2015524342A priority patent/JP6220874B2/en
Priority to KR1020157004648A priority patent/KR102118567B1/en
Priority to RU2015106020A priority patent/RU2632972C2/en
Application filed by Dow AgroSciences LLC filed Critical Dow AgroSciences LLC
Priority to PL13822431T priority patent/PL2877008T3/en
Priority to IN1385DEN2015 priority patent/IN2015DN01385A/en
Priority to SG11201500530RA priority patent/SG11201500530RA/en
Priority to MYPI2015700193A priority patent/MY181721A/en
Publication of WO2014018397A1 publication Critical patent/WO2014018397A1/en
Priority to IL236854A priority patent/IL236854B/en
Priority to PH12015500147A priority patent/PH12015500147B1/en
Anticipated expiration legal-status Critical
Priority to ZA2015/01145A priority patent/ZA201501145B/en
Ceased legal-status Critical Current

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    • E—FIXED CONSTRUCTIONS
    • E21—EARTH OR ROCK DRILLING; MINING
    • E21B—EARTH OR ROCK DRILLING; OBTAINING OIL, GAS, WATER, SOLUBLE OR MELTABLE MATERIALS OR A SLURRY OF MINERALS FROM WELLS
    • E21B44/00—Automatic control systems specially adapted for drilling operations, i.e. self-operating systems which function to carry out or modify a drilling operation without intervention of a human operator, e.g. computer-controlled drilling systems; Systems specially adapted for monitoring a plurality of drilling variables or conditions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof containing the group; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals

Definitions

  • herbicidal compositions comprising (a) 4-amino-3-chloro-5- fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) very long chain fatty acid (VLCFA) synthesis- inhibiting herbicides and fatty acid/lipid synthesis inhibiting herbicides.
  • VLCFA very long chain fatty acid
  • the ratio of compound (a) to compound (b) can be expressed in terms of weight to weight (g to g), gae/ha to gae/ha, gae/ha to gai/ha, or gai/ha to gai/ha.
  • a synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)
  • composition of embodiment 1 wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fenoxasulfone. 13. The composition of embodiment I, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fentrazamide.
  • composition of embodiment I wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) indanofan.
  • composition of any of embodiments 1-24, further comprising a herbicide safener comprising any of embodiments 1-24, further comprising a herbicide safener.
  • composition of embodiment 5, wherein the weight ratio of compound of formula (I) or agriculturally acceptable salt or ester thereof to acetochlor or agriculturally acceptable salt or ester thereof is from about 1 : 1680 to about 6: 1.
  • composition of embodiment 5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to alachlor or agriculturally acceptable salt or ester thereof is from about 1 :3350 to about 2: 1.
  • weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to anilofos or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to benfuresate or agriculturally acceptable salt or ester thereof is from about 1 :300 to about 6: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cafenstrole or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to dimethenamid-P or agriculturally acceptable salt or ester thereof is from about 1 :850 to about 1 : 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fenoxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fentrazamide or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 19: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to indanofan or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to flufenacet or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 12: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to mefenacet or agriculturally acceptable salt or ester thereof is from about 1 :800 to about 1 : 1.
  • composition of embodiment 5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to s-metolachlor or agriculturally acceptable salt or ester thereof is from about 1 : 1500 to about 4: 1. 38. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to molinate or agriculturally acceptable salt or ester thereof is from about 1 :2780 to about 1 : 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pethoxamid or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 1.5: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pretilachlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 8: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to prosulfocarb or agriculturally acceptable salt or ester thereof is from about 1 :2000 to about 1 : 1.5.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyroxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :200 to about 12: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thenylchlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 4: 1.
  • composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thiobencarb or agriculturally acceptable salt or ester thereof is from about 1 :2250 to about 1 :2.
  • composition of any of embodiments 1-44 further comprising an agriculturally acceptable adjuvant or carrier.
  • a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation the composition of any of embodiments 1-46.
  • a method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a compound of the formula (I)
  • sulfonylaminocarbonyltriazolinone- acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolerant crops.
  • HPPD 4-hydroxyphenyl-pyruvate dioxygenase
  • HPPD 4-hydroxyphenyl-pyruvate dioxygenase
  • HPPD phytoene desaturase inhibitor-
  • carotenoid biosynthesis inhibitor- carotenoid biosynthesis inhibitor-
  • resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple herbicide modes-of-action or via multiple resistance mechanisms.
  • the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3- phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) synthesis inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors,
  • ALS acetolactate syntha
  • composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to alachlor or agriculturally acceptable salt or ester thereof is from about 1 :3350 to about 2: 1.
  • composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to anilofos or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to benfuresate or agriculturally acceptable salt or ester thereof is from about 1 :300 to about 6: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cafenstrole or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to dimethenamid-P or agriculturally acceptable salt or ester thereof is from about 1 :850 to about 1 : 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fenoxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fentrazamide or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 19: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to indanofan or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
  • composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to flufenacet or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 12: 1.
  • weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to mefenacet or agriculturally acceptable salt or ester thereof is from about 1 :800 to about 1 : 1.
  • composition of any of embodiments 1 -5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to s-metolachlor or agriculturally acceptable salt or ester thereof is from about 1 : 1500 to about 4: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to molinate or agriculturally acceptable salt or ester thereof is from about 1 :2780 to about 1 : 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pethoxamid or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 1.5: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pretilachlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 8: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to prosulfocarb or agriculturally acceptable salt or ester thereof is from about 1 :2000 to about 1 : 1.5.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyroxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :200 to about 12: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thenylchlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 4: 1.
  • composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thiobencarb or agriculturally acceptable salt or ester thereof is from about 1 :2250 to about 1 :2.
  • composition of any of embodiments 1-48 or 60-98 further comprising an agriculturally acceptable adjuvant or carrier.
  • compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)
  • inhibiting herbicides include, but are not limited to, acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or acceptable salts and esters thereof.
  • the compositions may also contain an agriculturally acceptable adjuvant or carrier.
  • a compound of formula (I) or an agriculturally acceptable ester or salt thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides .
  • the compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has been described in U.S. Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety.
  • Exemplary uses of the compound of the formula (I) include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.
  • VLCFA and fatty acid/lipid synthesis inhibiting herbicides include the chemical classes of acetamides, chloroacetamides, oxyacetamides, tetrazolinones, benzofuranes, thiocarbamates, and phosphorodithioates. Without being limited to any theory, their herbicidal activity is attributed to inhibition of very-long-chain fatty acid (VLCFA, fatty acids, e.g., >C18) synthesis or fatty acid/lipid synthesis.
  • VLCFA very-long-chain fatty acid
  • VLCFA and fatty acid/lipid synthesis inhibiting herbicides include, but are not limited to acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or salts thereof.
  • acetochlor is 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6- methylphenyl)acetamide and possesses the following structure:
  • acetochlor includes its use for pre- emergence or pre-plant control of grasses, certain broadleaf weeds and yellow nutsedge, e.g. in maize, soybeans, peanuts, cotton, potatoes and sugar cane.
  • alachlor is 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamide and possesses the following structure:
  • alachlor S-[2-[(4-chlorophenyl)(l-methylethyl)amino]-2- oxoethyl] 0, 0-dimethyl phosphorodithioate and possesses the following structure:
  • anilofos include, e.g., its use for control of annual grassy weeds and sedges, e.g., in transplanted rice.
  • benfuresate is 2,3-dihydro-3,3-dimethyl-5-benzofuranyl
  • herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009.
  • Exemplary uses of benfuresate include its use for post-emergence control of grass and broadleaf weeds, e.g., in paddy rice, fruit, beans, maize, sugar cane and perennial crops.
  • butachlor is N-(butoxymethyl)-2-chloro-N-(2,6- diethylphenyl)acetamide and possesses the following structure:
  • cafenstrole is N,N-diethyl-3-[(2,4,6-trimethylphenyl)sulfonyl]-lH- 1,2,4-triazole-l-carboxamide and possesses the following structure:
  • Echinochloa oryzicola, Cyperus dijformis and other weeds e.g., in paddy rice.
  • dimethenamid is (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2- methoxy-l-methylethyl)acetamide and possesses the following structure:
  • the S isomer i.e., (S) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-l- methylethyl)acetamide has also been used as a herbicide.
  • dimethenamid is exemplified in Tomlin, C, ed. A World Compendium The Pesticide Manual. 15 th ed. Alton: BCPC Publications, 2009 (hereafter "The Pesticide Manual, Fifteenth Edition, 2009.”).
  • exemplary uses of dimethenamid include its use for pre- or early post-emergence control of annual grass and broadleaf weeds, e.g., in maize, soybeans, sugar beet, potatoes, dry beans and other crops.
  • fenoxasulfone is 3-[(2,5-dichoro-4-ethoxybenzyl)sulfonyl]-4,5- dihydro-5,5-dimethyl-l,2-oxazole and possesses the following structure:
  • fenoxasulfone Exemplary uses include its use in rice for control of barnyardgrass, annual broadleaf weeds, and needle spike rush.
  • fentrazamide is 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5- dihydro-5-oxo-lH-tetrazole-l-carboxamide and possesses the following structure:
  • fentrazamide has herbicidal activity as herbicidal activity. Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fentrazamide include its use for control of barnyard grass (Echinochloa spp.) and annual sedges, from weed pre-emergence, e.g., in rice.
  • flufenacet is N-(4-fluorophenyl)-N-(l-methylethyl)-2-[[5- (trifluoromethyl)-l,3,4-thiadiazol-2-yl]oxy]acetamide and possesses the following structure:
  • indanofan is (RS)-2-[[2-(3-chlorophenyl)oxiranyl]methyl]-2-ethyl- lH-indene-l,3(2H)-dione and possesses the following structure:
  • indanofan Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of indanofan include its use for pre-emergence and post-emergence weed control, e.g., in transplanted rice, and pre-emergence weed control in turf.
  • mefenacet is 2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide and possesses the following structure:
  • S-metolachlor is a mixture of 2-chloro-N-(2-ethyl-6-methylphenyl)- N-[(15)-2-methoxy-l-methylethyl]acetamide and 2-chloro-N-(2-ethyl-6-methylphenyl)-N- [(lR)-2-methoxy-l-methylethyl]acetamide, wherein the mixture contains predominantly S- isomer, e.g., 80-100%.
  • Metolachlor has the following formula:
  • S-metolachlor includes its use for control of annual grasses and broadleaf weeds, e.g., in maize, sorghum, cotton, sugar beet, fodder beet, sugar cane, potatoes, peanuts, soybeans, safflowers, sunflowers, various vegetables, fruit and nut trees, and woody ornamentals.
  • molinate is S-ethyl hexahydro-lH-azepine-l-carbothioate and possesses the following structure: Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of molinate include its use for control of germinating broadleaf and grass weeds, e.g., in rice.
  • pethoxamid is 2 -Chloro-N-(2-ethoxyethyl)-N-(2 -methyl- 1 -phenyl- 1- propen-l-yl)acetamide and possesses the following structure:
  • pethoxamid a monocotyledonous and annual broadleaf weeds, e.g., in corn/maize, oilseed rape and soybeans.
  • pretilachlor is 2-chloro-N-(2,6-diethylphenyl)-N-(2- propoxyethyl)acetamide and possesses the following structure:
  • pretilachlor Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pretilachlor include its use for control of annual grasses, broadleaf weeds and sedges, e.g., in transplanted and seeded rice.
  • prosulfocarb is ⁇ -(phenylmethyl) dipropylcarbamothioate and possesses the following structure:
  • prosulfocarb Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of prosulfocarb include its use for pre- and early post-emergence control of grass and broadleaf weeds, e.g., in winter wheat, winter barley and rye.
  • pyroxasulfone is 3-[[[5-(difluoromethoxy)-l-methyl-3- (trifluoromethyl)- lH-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole and possesses the following structure:
  • thenylchlor is 2-chloro-N-(2,6-dimethylphenyl)-N-[(3-methoxy-2- thienyl)methyl]acetamide and possesses the following structure:
  • herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009.
  • exemplary uses of thenylchlor include its use for pre-emergence control of annual grass and broadleaf weeds, e.g., in paddy rice.
  • thiobencarb is 5'-[(4-chlorophenyl)methyl] N,N-diethylcarbamothioate and possesses the following structure:
  • thiobencarb has herbicidal activity as herbicidal activity. Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of thiobencarb include its use for pre-emergence to early post-emergence control of Echinochloa, Leptochloa and Cyperus spp., and other monocotyledonous and annual broadleaf weeds, e.g., in direct-seeded and transplanted rice.
  • herbicide means a compound, e.g., active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
  • a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect to the vegetation e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.
  • controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation.
  • Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged vegetation, broadcast, spot, mechanical, water- injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.
  • plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
  • agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide.
  • exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
  • Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines.
  • Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula: R 1 R 2 R 3 R 4 N +
  • R 1 , R 2 , R 3 and R 4 each, independently represents hydrogen or d-C 12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C 1 -C 4 alkylthio or phenyl groups, provided that R 1 , R 2 , R 3 and R 4 are sterically compatible. Additionally, any two of R 1 , R 2 , R 3 and R 4 together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms.
  • Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
  • a metal hydroxide such as sodium hydroxide
  • an amine such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine
  • a tetraalkylammonium hydroxide such as tetramethylammonium hydroxide or choline hydroxide.
  • esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C1 0 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols.
  • Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C 1 -C 4 alkyl or C1-C4 alkoxy.
  • Esters can be prepared by coupling of the acids with the alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
  • suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI)
  • alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate
  • alkylating agents such as alky
  • herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)
  • the VLCFA or fatty acid/lipid synthesis inhibiting herbicide is acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s- metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salt thereof.
  • kits for controlling undesirable vegetation comprising contacting the vegetation or the locus thereof, i.e., the area adjacent to the vegetation with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of formula (I) or salt of ester thereof and (b) VLCFA or fatty acid/lipid synthesis inhibiting herbicides.
  • the methods employ the compositions described herein.
  • the herbicidal active ingredients are more effective in combination than when applied individually.
  • Synergism has been defined as "an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately.”
  • the compositions exhibit synergy as determined by the Colby's equation. Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.
  • the compound of formula (I), i.e., the carboxylic acid is employed.
  • a carboxylate salt of the compound of formula (I) is employed.
  • an aralkyl or alkyl ester is employed.
  • a benzyl, substituted benzyl, or Ci-4 alkyl, e.g., n-butyl ester is employed.
  • the benzyl ester is employed.
  • the compound of formula (I) or salt or ester thereof and acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or an agriculturally acceptable salt thereof are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
  • Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action.
  • compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature undesirable vegetation to achieve the maximum control of weeds.
  • compositions and methods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights-of-way (ROW).
  • crops including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops,
  • compositions and methods provided herein are utilized to control weeds in rice.
  • the rice is direct-seeded, water-seeded, or transplanted rice.
  • compositions and methods described herein may be used to control undesirable vegetation in glyphosate-tolerant-, 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicamba- tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, aceto
  • phenylpyrazolines ACCase inhibitors, imidazolinones, sulfonylureas,
  • compositions and methods may be used in controlling undesirable vegetation in crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or inhibitors of multiple modes of action.
  • the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed.
  • complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or sequentially.
  • compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
  • agronomic stress tolerance including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH
  • pest tolerance including but not limited to insects, fungi and pathogens
  • crop improvement traits including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture.
  • Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in direct-seeded, water-seeded, and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, ornamental species, aquatics, plantation crops, vegetables, industrial vegetation management (rVM) and rights of way (ROW).
  • rVM industrial vegetation management
  • ROW rights of way
  • the methods provided herein are utilized to control undesirable vegetation in rice.
  • the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA),
  • Echinochloa species Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass,
  • ECHCG Echinochloa crus-pavonis
  • Schult. gulf cockspur, ECHCV
  • Echinochloa colonum L.
  • LINK junglerice, ECHCO
  • Echinochloa oryzoides Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb.
  • MOOKA Monochoria vaginalis
  • the methods provided herein are utilized to control undesirable vegetation in cereals.
  • the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POA ), Setaria pumila (Poir.) Roemer & J.A.
  • the methods provided herein are utilized to control undesirable vegetation in range and pasture, fallowland, IVM and ROW.
  • the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L.
  • RUMOB Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
  • the methods provided herein are utilized to control undesirable vegetation found in row crops, tree and vine crops and perennial crops.
  • the methods provided herein are utilized to control undesirable vegetation found in row crops, tree and vine crops and perennial crops.
  • the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D.
  • Webster (broadleaf signalgrass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn.
  • the methods provided herein are utilized to control undesirable vegetation in turf.
  • the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L.
  • PLALA Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers
  • Trifolium repens L. white clover, TRFRE
  • Viola species wild violet, VIOSS
  • compositions and methods provided herein are utilized to control undesirable vegetation consisting of grass, broadleaf and sedge weeds.
  • the compositions and methods provided herein are utilized to control undesirable vegetation including Brachiaria, Brassica, Chenopodium, Cirsium, Cyperus, Digitaria, Echinochloa, Fimbristylis, Galium, Ipomoea, Ischaemum, Kochia, Leptochloa, Papaver, Polygonum, Salsola, Schoenoplectus, Sinapis, Stellaria and Xanthium.
  • the combination of compound (I) or agriculturally acceptable ester or salt thereof and VLCFA and fatty acid/lipid synthesis inhibiting herbicides or agriculturally acceptable salt or ester thereof is used to control Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brassica napus L. (winter oilseed rape, BRSNW), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L.
  • Brachiaria platyphylla Griseb.
  • Nash or Urochloa platyphylla Nash
  • R.D. Webster broadleaf signalgrass, BRAPP
  • Brassica napus L. winter oilseed rape, BRSNW
  • Cyperus esculentus L. yellow nutsedge, CY
  • Salisb. saramollagrass, ISCRU
  • Kochia scoparia L.
  • Schrad. kochia, KCHSC
  • Leptochloa chinensis L.
  • Nees Choinese sprangletop, LEFCH
  • Papaver rhoeas L. common poppy, PAPRH
  • Polygonum hydropiperoides Michx. POLHP, mild smartweed
  • Salsola tragus L. Russian thistle, SASKR
  • Schoenoplectus juncoides Rosapis arvensis L. (wild mustard, SINAR)
  • Stellaria media L.
  • Vill. common chickweed, STEME
  • Xanthium strumarium L. common cocklebur, XANST
  • the compounds of formula I or agriculturally acceptable salt or ester thereof may be used to control herbicide resistant or tolerant weeds.
  • the methods employing the combination of a compound of formula I or agriculturally acceptable salt or ester thereof and the compositions described herein may also be employed to control herbicide resistant or tolerant weeds.
  • Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas,
  • ALS acetolactate synthase
  • AHAS acetohydroxy acid synthase
  • inhibitors e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylamin
  • benzothiadiazinones nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines),, synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzo
  • Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
  • an agriculturally acceptable ester or salt of compound (I) is employed.
  • an agriculturally acceptable ester is employed.
  • the ester is a Ci_ 4 alkyl ester.
  • the ester is a benzyl ester.
  • compound (I), which is a carboxylic acid, is employed.
  • an agriculturally acceptable salt of acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb is employed in the methods or compositions described herein.
  • the compound of formula (I) or salt or ester thereof is used in combination with acetochlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 : 1680 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :46 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :90 to about 1 :2.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :46 to about 1 :5.5.
  • the compositions provided herein comprise the compound of formula (I) or its benzyl ester and acetochlor.
  • the composition comprises the compound of formula (I) and acetochlor, wherein the weight ratio of the compound of formula (I) to acetochlor is about 1 :46 to about 1 :5.5.
  • the composition comprises the benzyl ester of the compound of formula (I) and acetochlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to acetochlor is about 1 :23 to about 1 :5.5.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 3,660 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and acetochlor, e.g., sequentially or simultaneously.
  • the acetochlor is applied at a rate from about 50 gai/ha to about 3360 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 grams acid equivalent per hectare (gae/ha) to about 300 gae/ha. In some embodiments, the acetochlor is applied at a rate from about 50 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha.
  • the acetochlor is applied at a rate from about 100 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha.
  • the methods utilize the compound of formula (I), or its benzyl ester and acetochlor.
  • the methods utilize the compound of formula (I) and acetochlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and acetochlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with acetochlor are used to control BRAPP, DIGSA, ECHCG, ECHOR, CYPRO, LEFCH or FIMMI.
  • the compound of formula (I) or salt or ester thereof is used in combination with alachlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor is within the range of from about 1 :3350 to about 2: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor or salt or ester thereof is within the range of from about 1 : 1000 to about 1 :3.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor or salt or ester thereof is within the range of from about 1 :39 to about 1 :78.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and alachlor.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 172 grams active ingredient per hectare (gai/ha) to about 7000 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 174 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 1272 grams active ingredient per hectare (gai/ha) to about 2512 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and alachlor, e.g., sequentially or simultaneously.
  • the alachlor is applied at a rate from about 170 gai/ha to about 6700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and alachlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with alachlor are used to control IPOHE.
  • the compound of formula (I) or salt or ester thereof is used in combination with anilofos.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos or salt or ester thereof is within the range of from about 1 :250 to about 6: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1 :45 to about 1 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1 :50 to about 1 :3.
  • the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and anilofos.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 750 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and anilofos, e.g., sequentially or simultaneously.
  • the anilofos is applied at a rate from about 50 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the anilofos is applied at a rate from about 100 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and anilofos.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with anilofos are used to control ECHCG, ECHOR, CYPRO or FIMMI.
  • the compound of formula (I) or salt or ester thereof is used in combination with benfuresate.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :300 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 : 1 13 to about 1.33: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :70 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 : 70 to about 1 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :57 to about 1 : 1.8.
  • the compositions provided herein comprise the compound of formula (I) or its benzyl ester and benfuresate.
  • the composition comprises the compound of formula (I) and benfuresate, wherein the weight ratio of the compound of formula (I) to benfuresate is about 1 :57 to about 1 : 1.8.
  • the composition comprises the benzyl ester of the compound of formula (I) and benfuresate, wherein the weight ratio of the benzyl ester of the compound of formula (I) to benfuresate is about 1 :69 to about 1 :4.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 55 grams active ingredient per hectare (gai/ha) to about 242 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and benfuresate or salt or ester thereof, e.g., sequentially or simultaneously.
  • benfuresate is applied at a rate from about 50 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the benfuresate is applied at a rate from about 25 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 200 gae/ha. In some embodiments, the benfuresate is applied at a rate from about 50 gai/ha to about 600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and benfuresate.
  • the methods utilize the compound of formula (I) and benfuresate, wherein the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and benfuresate is applied at a rate of about 75 gai/ha to about 300 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and benfuresate, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and benfuresate is applied at a rate of about 75 gai/ha to about 600 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with benfuresate are used to control ECHCG, ECHCO, LEFCH, CYPIR, POLHP, SCPJU or ECHOR.
  • the compound of formula (I) or salt or ester thereof is used in combination with butachlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 :750 to about 3 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 : 103 to about 1 :6.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 :200 to about 1 :3.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 : 102 to about 1 :6.
  • the compositions provided herein comprise the compound of formula (I) or its benzyl or w-butyl ester and butachlor.
  • the composition comprises the compound of formula (I) and butachlor, wherein the weight ratio of the compound of formula (I) to butachlor is about 1 : 102 to about 1 :6.
  • the composition comprises the benzyl ester of the compound of formula (I) and butachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to butachlor is about 1 : 102 to about 1 :6.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 115 grams active ingredient per hectare (gai/ha) to about 1800 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 117 grams acid active ingredient per hectare (gai/ha) to about 468 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and butachlor, e.g., sequentially or simultaneously.
  • the butachlor is applied at a rate from about 113 gai/ha to about 1500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the butachlor or salt or ester thereof is applied at a rate from about 50 gai/ha to about 900 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the butachlor or salt or ester thereof is applied at a rate from about 112.5 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha.
  • the methods utilize the compound of formula (I), or its benzyl or w-butyl ester and butachlor. In one embodiment, the methods utilize the compound of formula (I) and butachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and butachlor is applied at a rate of about 112.5 gai/ha to about 450 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and butachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and butachlor is applied at a rate of about 1 12.5 gai/ha to about 450 gai/ha.
  • gae/ha g acid equivalent per hectare
  • butachlor is applied at a rate of about 1 12.5 gai/ha to about 450 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with butachlor are used to control ECHCO, LEFCH, BRAPP, IPOHE, ECHCG, ECHOR, or CYPRO.
  • the compound of formula (I) or salt or ester thereof is used in combination with cafenstrole.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 : 150 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 : 24 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 :50 to about 2: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 :24 to about 1 : 1.5.
  • the compositions provided herein comprise the compound of formula (I) or its benzyl ester and cafenstrole.
  • the composition comprises the compound of formula (I) and cafenstrole, wherein the weight ratio of the compound of formula (I) to cafenstrole is about 1 :24 to about 1 : 1.5.
  • the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1 :24 to about 1 : 1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1 :47 to about 2.7: 1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 30 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and cafenstrole, e.g., sequentially or simultaneously.
  • the cafenstrole is applied at a rate from about 26 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the cafenstrole is applied at a rate from about 10 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha.
  • the cafenstrole is applied at a rate from about 26.3 gai/ha to about 105 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha.
  • the methods utilize the compound of formula (I), or its benzyl ester and cafenstrole.
  • the methods utilize the compound of formula (I) and cafenstrole, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 70 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 210 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cafenstrole are used to control BRAPP, ECHCG, ECHCO, LEFCH, IPOHE, CYPIR, ECHOR, SCPJU or CYPRO.
  • the compound of formula (I) or salt or ester thereof is used in combination with dimethenamid-P.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1 :850 to about 1 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1 :205 to about 1 :8.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 2,000 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 283 grams active ingredient per hectare (gai/ha) to about 1,670 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and dimethenamid-P, e.g., sequentially or simultaneously.
  • the dimethenamid-P is applied at a rate from about 280 gai/ha to about 1,700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the dimethenamid-P is applied at a rate from about 275 gai/ha to about 1,640 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P are used to control ECHCO, CYPES, and XANST.
  • the compound of formula (I) or salt or ester thereof is used in combination with fenoxasulfone.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxasulfone is within the range of from about 1 :250 to about 6: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxasulfone is within the range of from about 1 :46 to about 1 : 1.
  • the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and fenoxasulfone.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 53 grams acid active ingredient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fenoxasulfone, e.g., sequentially or simultaneously.
  • the fenoxasulfone is applied at a rate from about 50 gai/ha to about 500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the fenoxasulfone is applied at a rate from about 50 gai/ha to about 500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and fenoxasulfone.
  • the compound of formula (I) or salt or ester thereof is used in combination with fentrazamide.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 150 to about 19: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 15 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 :68 to about 2: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 :32 to about 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 16 to about 1 : 1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fentrazamide. In one embodiment, the composition comprises the compound of formula (I) and fentrazamide, wherein the weight ratio of the compound of formula (I) to fentrazamide is about 1 : 16 to about 1 : 1.5.
  • the composition comprises the benzyl ester of the compound of formula (I) and fentrazamide, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fentrazamide is about 1 : 19 to about 1 :2.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 18 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 20 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fentrazamide, e.g. , sequentially or simultaneously.
  • fentrazamide is applied at a rate from about 16 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the fentrazamide is applied at a rate from about 7 gai/ha to about 140 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha.
  • the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha.
  • the fentrazamide is applied at a rate from about 16.9 gai/ha to about 67.5 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha.
  • the methods utilize the compound of formula (I), or its benzyl ester and fentrazamide.
  • the methods utilize the compound of formula (I) and fentrazamide, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and fentrazamide is applied at a rate of about 16.9 gai/ha to about 67.5 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and fentrazamide, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and fentrazamide is applied at a rate of about 33.8 gai/ha to about 300 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with fentrazamide are used to control BRAPP, ECHCG, ECHCO, LEFCH, DIGSA, or ECHOR.
  • the compound of formula (I) or salt or ester thereof is used in combination with flufenacet.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :625 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :68 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :300 to about 1 :2.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and flufenacet.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 1550 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 62 grams active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 300 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and flufenacet, e.g., sequentially or simultaneously.
  • the flufenacet is applied at a rate from about 25 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the flufenacet is applied at a rate from about 60 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and flufenacet.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with flufenacet are used to control BRAPP, CIRAR, CHEAL, KCHSC, PAPRH, SASKR, SINAR and STEME
  • the compound of formula (I) or salt or ester thereof is used in combination with indanofan.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1 : 150 to about 12: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1 : 136 to about 6: 1.
  • the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and indanofan.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 30 grams acid active ingredient per hectare (gai/ha) to about 450 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and indanofan, e.g., sequentially or simultaneously.
  • the indanofan is applied at a rate from about 25 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the indanofan is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and indanofan.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with indanofan are used to control ECHCO and LEFCH.
  • the compound of formula (I) or salt or ester thereof is used in combination with mefenacet.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 :800 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 :727 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 : 150 to about 1 :2.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and mefenacet.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 252 grams active ingredient per hectare (gai/ha) to about 1900 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 255 grams acid active ingredient per hectare (gai/ha) to about 1750 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and mefenacet or salt thereof, e.g., sequentially or simultaneously.
  • the mefenacet is applied at a rate from about 250 gai/ha to about 1600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the mefenacet is applied at a rate from about 50 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n- butyl ester and mefenacet.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with mefenacet are used to control BRAPP, LEFCH, CYPIR or ECHOR.
  • the compound of formula (I) or salt or ester thereof is used in combination with s-metolachlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 1500 to about 4: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 1000 to about 1 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 194 to about 1 : 12.
  • the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and s-metolachlor.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 72 grams active ingredient per hectare (gai/ha) to about 3300 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 73 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and s-metolachlor, e.g., sequentially or simultaneously.
  • the s-metolachlor is applied at a rate from about 70 gai/ha to about 3000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the s-metolachlor is applied at a rate from about 387 gai/ha to about 1550 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and s-metolachlor.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-metolachlor are used to control ECHCG or IPOHE.
  • the compound of formula (I) or salt or ester thereof is used in combination with molinate.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 :2780 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 :255 to about 1 :8. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 : 194 to about 1 :44.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and molinate.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 5860 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 284 grams active ingredient per hectare (gai/ha) to about 1155 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 1408 grams active ingredient per hectare (gai/ha) to about 2832 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and molinate, e.g., sequentially or simultaneously.
  • the molinate is applied at a rate from about 280 gai/ha to about 5560 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the molinate is applied at a rate from about 1400 gai/ha to about 2800 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and molinate.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-molinate are used to control ECHOR.
  • the compound of formula (I) or salt or ester thereof is used in combination with pethoxamid.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1 :625 to about 1.5: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1 : 150 to about 1 : 10. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pethoxamid. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 202 grams active ingredient per hectare (gai/ha) to about 1,550 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 313 grams acid active ingredient per hectare (gai/ha) to about 1,252 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pethoxamid, e.g., sequentially or simultaneously.
  • the pethoxamid is applied at a rate from about 200 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pethoxamid is applied at a rate from about 305 gai/ha to about 1,220 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester in combination with pethoxamid are used to control IPOHE, LEFCH, CYPES or CYPIR.
  • the compound of formula (I) or salt or ester thereof is used in combination with pretilachlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :375 to about 8: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :34 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 : 64 to about 1 : 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :32 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :91 to about 2.7: 1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and pretilachlor. In one embodiment, the composition comprises the compound of formula (I) and pretilachlor, wherein the weight ratio of the compound of formula (I) to pretilachlor is about 1 :34 to about 1 :2.
  • the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1 :32 to about 1 :4. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1 :91 to about 2.7: 1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 40 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 43 grams active ingredient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pretilachlor, e.g., sequentially or simultaneously.
  • the pretilachlor is applied at a rate from about 38 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 18 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha.
  • the pretilachlor is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 37.5 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and pretilachlor.
  • the methods utilize the compound of formula (I) and pretilachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 150 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and pretilachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 400 gai/ha.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pretilachlor are used to control BRAPP, ECHCO, DIGSA, CYPIR, ECHCG, ECHOR, CYPRO, FIMMI, or SCPJU.
  • the compound of formula (I) or salt or ester thereof is used in combination with prosulfocarb.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 :2000 to about 1 : 1.5. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 : 1818 to about 1 : 10. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 : 1600 to about 1 : 100.
  • the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and prosulfocarb.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 502 grams active ingredient per hectare (gai/ha) to about 4300 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 510 grams acid active ingredient per hectare (gai/ha) to about 4050 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 1,002 grams acid active ingredient per hectare (gai/ha) to about 4010 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and prosulfocarb, e.g., sequentially or simultaneously.
  • the prosulfocarb is applied at a rate from about 500 gai/ha to about 4000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the prosulfocarb is applied at a rate from about 1 ,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.0 gae/ha to about 100 gae/ha. In some embodiments, the prosulfocarb is applied at a rate from about 1,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.5 gae/ha to about 10 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and prosulfocarb.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with prosulfocarb are used to control BRSNW, CHEAL, GALAP, KCHSC, PAPRH, SASKR, SINAR and STEME.
  • the compound of formula (I) or salt or ester thereof is used in combination with pyroxasulfone.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1 :200 to about 12: 1.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1 : 15 to about 1 : 1.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 700 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 37 grams acid active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pyroxasulfone, e.g., sequentially or simultaneously.
  • the pyroxasulfone is applied at a rate from about 25 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the pyroxasulfone is applied at a rate from about 30 gai/ha to about 120 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pyroxasulfone are used to control ECHCG or BRAPP.
  • the compound of formula (I) or salt or ester thereof is used in combination with thenylchlor.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :375 to about 4: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :341 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :34 to about 1 : 1.
  • the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 77 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 79 grams acid active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 143 grams acid active ingredient per hectare (gai/ha) to about 302 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thenylchlor, e.g., sequentially or simultaneously.
  • the thenylchlor is applied at a rate from about 75 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the thenylchlor is applied at a rate from about 135 gai/ha to about 270 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha.
  • the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor.
  • the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thenychlor or salt or ester thereof are used to control ECHOR and LEFCH.
  • the compound of formula (I) or salt or ester thereof is used in combination with thiobencarb.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :2250 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :51 1 to about 1 :32. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :510 to about 1 : 17.
  • the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 : 1000 to about 1 : 16. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :511 to about 1 :32. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and thiobencarb.
  • the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 : 16. In one embodiment, the composition comprises the compound of formula (I) and thiobencarb, wherein the weight ratio of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 :32.
  • the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 :64.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
  • the composition is applied at an application rate of from about 562 grams active ingredient per hectare (gai/ha) to about 4,800 gai/ha based on the total amount of active ingredients in the composition.
  • the composition is applied at an application rate of from about 564 grams active ingredient per hectare (gai/ha) to about 2275 gai/ha based on the total amount of active ingredients in the composition.
  • the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thiobencarb, e.g., sequentially or simultaneously.
  • the thiobencarb is applied at a rate from about 560 gai/ha to about 4500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
  • the thiobencarb is applied at a rate from about 280 gai/ha to about 5000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the thiobencarb is applied at a rate from about 560 gai/ha to about 2240 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha.
  • the methods utilize the compound of formula (I), or its benzyl ester and thiobencarb. In one embodiment, the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha.
  • the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha.
  • the methods utilize the benzyl ester of the compound of formula (I) and thiobencarb, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.83 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha.
  • compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thiobencarb or salt or ester thereof are used to control ECHOR, CYPRO, DIGSA, CYPIR, ISCRU or ECHCO.
  • the components of the mixtures described herein can be applied either separately or as part of a multipart herbicidal system.
  • the mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation.
  • the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides.
  • herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotry
  • bicyclopyrone bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben,
  • compositions and methods described herein can further be used in conjunction with glyphosate, 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines,
  • EPP 5 -enolpyruvylshikimate-3 -phosphate
  • sulfonylaminocarbonyltriazolinones acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil on glyphosate- tolerant, EPSP synthase inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryl
  • the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed.
  • complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or as a sequential application.
  • compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity.
  • herbicide safeners such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide
  • the safeners are employed in rice, cereal, corn, or maize settings.
  • the safener is cloquintocet or an ester or salt thereof.
  • cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals.
  • the safener is cloquintocet (mexyl).
  • compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide, a-naphthaleneacetic acids, benzyladenine, 4- hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, unic
  • the plant growth regulators are employed in one or more crops or settings, such as rice, cereal crops, corn, maize, broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane, sunflower, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, plantation crops, vegetables, and non-crop (ornamentals) settings.
  • the plant growth regulator is mixed with the compound of formula (I), or mixed with the compound of formula (I) and VLCFA inhibitors or fatty acid/lipid synthesis inhibitors to cause a preferentially advantageous effect on plants.
  • compositions provided herein further comprise at least one agriculturally acceptable adjuvant or carrier.
  • Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients.
  • Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a pre-mix or tank mixed.
  • Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; Cg-Cn alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (Cu-Cw) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
  • Liquid carriers that can be employed include water and organic solvents.
  • the organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, w-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarbox
  • organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like.
  • Water is the carrier for the dilution of concentrates.
  • Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
  • compositions described herein further comprise one or more surface-active agents.
  • surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application.
  • the surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes.
  • Surfactants which may also be used in the present formulations are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in “Encyclopedia of Surfactants," Vol. I-III, Chemical Publishing Co., New York, 1980-81.
  • Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate;
  • alkylarylsulfonate salts such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci 6 ethoxylate; soaps, such as sodium stearate; alkyl- naphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and
  • these materials can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
  • compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants,
  • compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
  • the concentration of the active ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight.
  • the active ingredients in certain embodiments, are present in a concentration from about 0.1 to 98 weight percent, and in certain embodiment's about 0.5 to 90 weight percent.
  • Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application.
  • the diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingredient and in certain embodiments contain about 0.01 to 7.0 weight percent.
  • compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
  • Results in Examples I, II, III, and IV are greenhouse trial results.
  • Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 80 to 20 ratio.
  • the soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm 2 ). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied.
  • the plants were grown for 8-22 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C during the day and 26° C during the night.
  • Nutrients Pigters Excel ® 15-5-15 5-Ca 2-Mg and iron chelate were applied in the irrigation solution as needed and water was added on a regular basis.
  • Supplemental lighting was provided with overhead metal halide 1000- Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
  • Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis.
  • VLCFA very long chain fatty acid
  • acetochlor (technical grade material)
  • acetochlor + dichlormid formulated as Topnotch ®
  • pretilachlor technical grade material
  • Butachlor butachlor formulated as Butachlor EC
  • fentrazamide formulated as Fentrazamide EC
  • thiobencarb formulated as Bolero ® 8EC
  • cafenstrole formulated as Himeadow ® WP or Lapost ® Flowable
  • benfuresate formulated as Full Shot ®
  • indanofan (technical grade material)
  • flufenacet formulated as Define ® DF
  • mefenacet (technical grade material)
  • S-metolachlor formulated as Dual ® II Magnum, pethoxamid formulated as Successor ® 600
  • Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.
  • weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated.
  • Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g. , 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate.
  • the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
  • weighed amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate.
  • additional water and/or 97:3 v/v acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
  • Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m 2 at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
  • the treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds.
  • gai/ha refers to active ingredient of acetachlor.
  • gai/ha refers to active ingredient of acetachlor.
  • compositions on Weed Control in a Rice Cropping System Compositions on Weed Control in a Rice Cropping System.
  • Herbicidal Compositions on Weed Control in a Rice Cropping System are Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Brachiaria platyphylla (Griseb.) Nash signalgrass, broadleaf CYPIR Cyperus iria L. flatsedge, rice
  • gae/ha grams acid equivalent per hectare
  • gai/ha j grams active ingredient per hectare
  • mud puddled soil
  • mud puddled soil
  • the prepared mud was dispensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm 2 ) leaving a headspace of 3 centimeters (cm) in each pot.
  • Mud was allowed to dry overnight prior to planting or transplanting.
  • Gro MetroMix® 306 planting mixture which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 840 mL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm 2 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29 C during the day and 26°C during the night.
  • Nutrients were added as Osmocote ® (19:6: 12, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
  • Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) each formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis.
  • the herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis-inhibiting herbicides acetochlor (technical grade material), acetochlor + dichlormid formulateded as Topnotch ® , pretilachlor (technical grade material), butachlor formulated as Butachlor EC, fentrazamide formulated as Fentrazamide EC, thiobencarb formulated as Bolero ® 8EC, cafenstrole formulated as Himeadow ® WP or Lapost ® Flowable, benfuresate formulated as Full Shot ® , anilofos (technical grade material), mefenacet (technical grade material), molinate (technical grade material), and thenylchlor (technical grade material). Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, an
  • test compound 200 mL glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex ® crop oil concentrate to obtain application solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • a weighed amount was placed in an individual 100 to 200 mL glass vial and was dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • the concentrated stock solutions obtained were diluted with an equivalent volume of an aqueous mixture containing 2.5% (v/v) crop oil concentrate so that the final application solutions contained 1.25% (v/v) crop oil concentrate.
  • Applications were made by injecting with a pipetter appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that all treated plant material received the same concentrations of acetone and crop oil concentrate.
  • the treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
  • A observed efficacy of active ingredient A at the same concentration as used in the mixture.
  • B observed efficacy of active ingredient B at the same concentration as used in the mixture.
  • Table 28 Synergistic Activity of In- Water Applications of Compound A Acid and Acetochlor + Dichlormid Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
  • *gai/ha refers to active ingredient of acetachlor.
  • gai/ha refers to active ingredient of acetachlor.
  • Table 30 Synergistic Activity of In- Water Applications of Compound A Acid and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 31 Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Herbicidal Compositions on Weed Control in a Rice Cropping System are Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 33 Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Butachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 34 Synergistic Activity of In- Water Applications of Compound A Acid and Fentrazamide Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 36 Synergistic Activity of In- Water Applications of Compound A Acid and Thiobencarb Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 40 Synergistic Activity of In- Water Applications of Compound A Acid and cafenstrole (Lapost ® Flowable) Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 45 Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Indanofan Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • Table 48 Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Thenylchlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
  • gae/ha grams acid equivalent per hectare
  • gai/ha ⁇ jrams active ingredient per hectare
  • Example III Evaluation of Post-emergence Foliar- Applied Herbicidal Mixtures for Weed Control in Cereal Crops in the Greenhouse.
  • Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm 2 ).
  • a fungicide treatment and/or other chemical or physical treatment was applied.
  • the plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C during the day and 17° C during the night.
  • Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000- Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
  • Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC (suspension concentrate), and a second cereal herbicide alone and in combination.
  • Compound A 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid
  • SC suspension concentrate
  • Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingredients in two- and three-way combinations.
  • Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m 2 ) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
  • the treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
  • Herbicidal Compositions on Weed Control in a Cereal Cropping System Herbicidal Compositions on Weed Control in a Cereal Cropping System.
  • Herbicidal Compositions on Weed Control in a Cereal Cropping System Herbicidal Compositions on Weed Control in a Cereal Cropping System.
  • Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil (32 percent silt, 23 percent clay, and 45 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and calcareous grit in an 80 to
  • the soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm 2 ).
  • Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) formulated as an SC
  • herbicidal components alone and in combination.
  • VLCFA very long chain fatty acid
  • Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.
  • weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated.
  • Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) COC so that the final spray solutions contain 1.25% (v/v) COC.
  • the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
  • weighed amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) COC or water to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated.
  • Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) COC so that the final spray solutions contained 1.25% (v/v) COC.
  • additional water and/or 97:3 (v/v) acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
  • Spray solutions were applied to the soil with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m 2 at a spray height of 18 inches (46 cm) above average pot height. Control pots were sprayed in the same manner with the solvent blank.
  • the treated and control pots were placed in a greenhouse and top watered as needed. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The pots were maintained in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters ® Excel 15-5-15 5-Ca 2-Mg) were applied in the irrigation solution as needed and water was added on a regular basis. Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. After
  • test plants were determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
  • gae/ha grams acid equivalent per hectare
  • gai/ha grams active ingredient per hectare
  • Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound A) formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination.
  • Compound A 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid
  • SC suspension concentrate
  • VLCFA very long chain fatty acid
  • Compound A benzyl ester SC was once diluted in 100 mL water in the 200 mL bottle/plot to achieve the desired rates and applied by water injection. Water injection applications were made by hand as evenly as possible. Pretilachlor was applied by hand, and benfuresate was applied using a pipette to achieve the desired rates. Each compound in mixture treatments was applied separately and successively. Water depth was 3 cm at application. Treatments were rated at 25 and 40 days after application (DAA) for post and pre-emergence trials respectively as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
  • DAA application
  • weed spectrum included, but was not limited to, common barnyardgrass (Echinochloa crus-galli, ECHCG), monochoria (Monochoria vaginalis, MOOVA), Japanese bulrush (Scirpus juncoides,SCPKS), kuroguwai (Eieocharis kuroguwai, ELOKU), common falsepimpernel (Lindernia pyxidaria, LIDPY), Souchet tardif (Cyperus serotinus, CYPSE), small-flower flatsedge (Cyperus difformis, CYPDI), American waterwort (Elatine triandra, ELTTR), and swamp smartweed (Polygonum hydropiperoides, POLHP).
  • gai/ha grams active ingredient per hectare

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Abstract

Provided herein are synergistic herbicidal compositions containing (a) a compound of formula (I): 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof, or an agriculturally acceptable salt or ester thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides, including but not limited to, acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salt or ester thereof, provide synergistic weed control of undesirable vegetation in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn or maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallow land, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) or rights-of-way (ROW).

Description

HERBICIDAL COMPOSITIONS COMPRISING 4-AMINO-3-CHLORO-5-FLUORO-6-(4- CHLORO-2-FLUORO-3-METHOXYPHENYL) PYRIDINE-2-CARBOXYLIC ACID OR A DERIVATIVE THEREOF AND VLCFA SYNTHESIS AND FATTY ACID/LIPID
SYNTHESIS INHIBITING HERBICIDES
Priority Claim
This application claims the benefit of United States provisional patent application number 61/675, 105 filed on July 24, 2012, and United States patent application serial number 13/840,306 filed on March 15, 2013, the disclosure of each of which is incorporated herein by reference in its entirety.
Field
Provided herein are herbicidal compositions comprising (a) 4-amino-3-chloro-5- fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) very long chain fatty acid (VLCFA) synthesis- inhibiting herbicides and fatty acid/lipid synthesis inhibiting herbicides.
Provided herein are also methods of controlling undesirable vegetation comprising applying (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides.
Background
The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.
Summary
Several embodiments are recited below. In the embodiments, the ratio of compound (a) to compound (b) can be expressed in terms of weight to weight (g to g), gae/ha to gae/ha, gae/ha to gai/ha, or gai/ha to gai/ha.
1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000003_0001
or an agriculturally acceptable salt or ester thereof and (b) VLCFA or fatty acid/lipid synthesis inhibiting herbicides.
2. The composition of embodiment 1, wherein (a) is a C1-4 alkyl or benzyl ester of compound (I).
3. The composition of embodiment 2, wherein (a) is a benzyl ester of compound (I).
4. The composition of embodiment 1, wherein (a) is the compound of formula (I), which is the carboxylic acid.
5. The composition of any of embodiments 1-4, wherein (b) is acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, or thiobencarb, or an agriculturally acceptable salt thereof.
6. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is acetochlor or acetochlor+dichlormid.
7. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is alachlor.
8. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is anilofos.
9. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is benfuresate.
10. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cafenstrole.
1 1. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is dimethenamid-P.
12. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fenoxasulfone. 13. The composition of embodiment I, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fentrazamide.
14. The composition of embodiment I, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) indanofan.
15. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is flufenacet.
16. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is mefenacet.
17. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is s-metolachlor.
18. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is molinate.
19. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pethoxamid.
20. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pretilachlor.
21. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is prosulfocarb.
22. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyroxasulfone.
23. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is thenylchlor.
24. The composition of embodiment 1, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is thiobencarb.
25. The composition of any of embodiments 1-24, further comprising a herbicide safener.
26. The composition of embodiment 5, wherein the weight ratio of compound of formula (I) or agriculturally acceptable salt or ester thereof to acetochlor or agriculturally acceptable salt or ester thereof is from about 1 : 1680 to about 6: 1.
27. The composition of embodiment 5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to alachlor or agriculturally acceptable salt or ester thereof is from about 1 :3350 to about 2: 1. 28. The composition of embodiment 5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to anilofos or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
29. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to benfuresate or agriculturally acceptable salt or ester thereof is from about 1 :300 to about 6: 1.
30. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cafenstrole or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
31 The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to dimethenamid-P or agriculturally acceptable salt or ester thereof is from about 1 :850 to about 1 : 1.
32. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fenoxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
33. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fentrazamide or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 19: 1.
34. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to indanofan or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
35. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to flufenacet or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 12: 1.
36. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to mefenacet or agriculturally acceptable salt or ester thereof is from about 1 :800 to about 1 : 1.
37. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to s-metolachlor or agriculturally acceptable salt or ester thereof is from about 1 : 1500 to about 4: 1. 38. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to molinate or agriculturally acceptable salt or ester thereof is from about 1 :2780 to about 1 : 1.
39. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pethoxamid or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 1.5: 1.
40. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pretilachlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 8: 1.
41. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to prosulfocarb or agriculturally acceptable salt or ester thereof is from about 1 :2000 to about 1 : 1.5.
42. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyroxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :200 to about 12: 1.
43. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thenylchlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 4: 1.
44. The composition of embodiment 5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thiobencarb or agriculturally acceptable salt or ester thereof is from about 1 :2250 to about 1 :2.
45. The composition of any of embodiments 1-44 further comprising an agriculturally acceptable adjuvant or carrier.
46. The composition of any of embodiments 1-44, which is synergistic as determined by the Colby equation.
47. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation the composition of any of embodiments 1-46.
48. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000007_0001
or an agriculturally acceptable salt or ester thereof and (b) a VLCFA or fatty acid/lipid synthesis inhibiting herbicide.
49. The method of embodiment 47 or 48, wherein the method is practied in at least one member of the group consisting of direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (TVM) or rights-of-way (ROW).
50. The method of embodiment 47 or 48, wherein the undesirable vegetation is immature.
51. The method of embodiment 47 or 48, wherein the (a) and (b) are applied to water.
52. The method of embodiment 51 , wherein the water is part of a flooded rice paddy.
53. The method of embodiment 47 or 48, wherein the (a) and (b) are applied pre- emergently to the weed or the crop.
54. The method of embodiment 47 or 48, wherein the (a) and (b) are applied post- emergently to the weed or the crop.
55. The method of any of embodiments 47 or 48, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinones-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-,
sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolerant crops.
56. The method of embodiment 53, wherein the tolerant crop possesses multiple or stacked traits conferring tolerance to multiple herbicides or multiple herbicide modes of action.
57. The method of embodiment 47 or 48, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.
58. The method of embodiment 57, wherein the resistant or tolerant weed is a biotype with resistance or tolerance to multiple herbicides, multiple chemical classes, multiple herbicide modes-of-action or via multiple resistance mechanisms.
59. The method of embodiment 58, wherein the resistant or tolerant weed is a biotype resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshikimate-3- phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) synthesis inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, difenzoquat, endothall, or organoarsenicals.
60. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is acetochlor or acetochlor+dichlormid.
61. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is alachlor.
62. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is anilofos.
63. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is benfuresate.
64. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cafenstrole. 65. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is dimethenamid-P
66. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fenoxasulfone.
67. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is fentrazamide.
68. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) indanofan.
69. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is flufenacet.
70. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is mefenacet.
70. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is s-metolachlor.
72. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is molinate.
73. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pethoxamid.
74. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pretilachlor.
75. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is prosulfocarb.
76. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pyroxasulfone.
77. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is thenylchlor.
78. The composition of any of embodiments 1-5, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is thiobencarb.
79. The composition of any of embodiments 1-48 or 60-78, further comprising a herbicide safener. 80. The composition of any of embodiments 1-5, wherein the weight ratio of compound of formula (I) or agriculturally acceptable salt or ester thereof to acetochlor or agriculturally acceptable salt or ester thereof is from about 1 : 1680 to about 6: 1.
81. The composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to alachlor or agriculturally acceptable salt or ester thereof is from about 1 :3350 to about 2: 1.
82. The composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to anilofos or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
83. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to benfuresate or agriculturally acceptable salt or ester thereof is from about 1 :300 to about 6: 1.
84. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to cafenstrole or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
85. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to dimethenamid-P or agriculturally acceptable salt or ester thereof is from about 1 :850 to about 1 : 1.
86. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fenoxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :250 to about 6: 1.
87. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to fentrazamide or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 19: 1.
88. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to indanofan or agriculturally acceptable salt or ester thereof is from about 1 : 150 to about 12: 1.
89. The composition of any of embodiments 1-5 wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to flufenacet or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 12: 1. 90. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to mefenacet or agriculturally acceptable salt or ester thereof is from about 1 :800 to about 1 : 1.
91. The composition of any of embodiments 1 -5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to s-metolachlor or agriculturally acceptable salt or ester thereof is from about 1 : 1500 to about 4: 1.
92. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to molinate or agriculturally acceptable salt or ester thereof is from about 1 :2780 to about 1 : 1.
93. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pethoxamid or agriculturally acceptable salt or ester thereof is from about 1 :625 to about 1.5: 1.
94. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pretilachlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 8: 1.
95. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to prosulfocarb or agriculturally acceptable salt or ester thereof is from about 1 :2000 to about 1 : 1.5.
96. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pyroxasulfone or agriculturally acceptable salt or ester thereof is from about 1 :200 to about 12: 1.
97. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thenylchlor or agriculturally acceptable salt or ester thereof is from about 1 :375 to about 4: 1.
98. The composition of any of embodiments 1-5, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to thiobencarb or agriculturally acceptable salt or ester thereof is from about 1 :2250 to about 1 :2.
99. The composition of any of embodiments 1-48 or 60-98 further comprising an agriculturally acceptable adjuvant or carrier.
100. The composition of any of embodiments 1-48 or 60-99, which is synergistic as determined by the Colby equation. Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000012_0001
or an agriculturally acceptable salt or ester of thereof, and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides. Exemplary inhibiting herbicides include, but are not limited to, acetochlor, alachlor, anilofos, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or acceptable salts and esters thereof. The compositions may also contain an agriculturally acceptable adjuvant or carrier.
Provided herein are also methods of controlling undesirable vegetation comprising applying (a) a compound of formula (I) or an agriculturally acceptable ester or salt thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides .
Detailed Description
DEFINITIONS
As used herein, the co llowing structure:
Figure imgf000012_0002
The compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2- fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid and has been described in U.S. Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of the formula (I) include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations. Exemplary VLCFA and fatty acid/lipid synthesis inhibiting herbicides include the chemical classes of acetamides, chloroacetamides, oxyacetamides, tetrazolinones, benzofuranes, thiocarbamates, and phosphorodithioates. Without being limited to any theory, their herbicidal activity is attributed to inhibition of very-long-chain fatty acid (VLCFA, fatty acids, e.g., >C18) synthesis or fatty acid/lipid synthesis. Exemplary VLCFA and fatty acid/lipid synthesis inhibiting herbicides include, but are not limited to acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or salts thereof.
As used herein, acetochlor is 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6- methylphenyl)acetamide and possesses the following structure:
Figure imgf000013_0001
Its herbicidal activity is exemplified in Tomlin, C, ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereafter "The Pesticide Manual, Fifteenth Edition, 2009."). Exemplary uses of acetochlor include its use for pre- emergence or pre-plant control of grasses, certain broadleaf weeds and yellow nutsedge, e.g. in maize, soybeans, peanuts, cotton, potatoes and sugar cane.
As used herein, alachlor is 2-chloro-N-(2,6-diethylphenyl)-N- (methoxymethyl)acetamide and possesses the following structure:
Figure imgf000013_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of alachlor include its use for pre-emergence control of annual grasses and many broadleaf weeds, e.g., in cotton, brassicas, maize, oilseed rape, peanuts, radish, soybeans and sugar cane. As used herein, anilofos is S-[2-[(4-chlorophenyl)(l-methylethyl)amino]-2- oxoethyl] 0, 0-dimethyl phosphorodithioate and possesses the following structure:
Figure imgf000014_0001
Its herbicidal activity is described in Journal of Applied Toxicology 2007, 27, 255- 261. Exemplary uses of anilofos include, e.g., its use for control of annual grassy weeds and sedges, e.g., in transplanted rice.
As used herein, benfuresate is 2,3-dihydro-3,3-dimethyl-5-benzofuranyl
ethanesulfonate and possesses the following structure:
Figure imgf000014_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of benfuresate include its use for post-emergence control of grass and broadleaf weeds, e.g., in paddy rice, fruit, beans, maize, sugar cane and perennial crops.
As used herein, butachlor is N-(butoxymethyl)-2-chloro-N-(2,6- diethylphenyl)acetamide and possesses the following structure:
Figure imgf000014_0003
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of butachlor include its use for pre-emergence control of annual grasses and certain broadleaf weeds, e.g., in rice, both seeded and transplanted.
As used herein, cafenstrole is N,N-diethyl-3-[(2,4,6-trimethylphenyl)sulfonyl]-lH- 1,2,4-triazole-l-carboxamide and possesses the following structure:
Figure imgf000015_0001
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of cafenstrole include its use for pre- and post-emergence control of
Echinochloa oryzicola, Cyperus dijformis and other weeds, e.g., in paddy rice.
As used herein, dimethenamid is (RS)-2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2- methoxy-l-methylethyl)acetamide and possesses the following structure:
Figure imgf000015_0002
The S isomer, i.e., (S) 2-chloro-N-(2,4-dimethyl-3-thienyl)-N-(2-methoxy-l- methylethyl)acetamide has also been used as a herbicide. Herbicidal activity for
dimethenamid is exemplified in Tomlin, C, ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereafter "The Pesticide Manual, Fifteenth Edition, 2009."). Exemplary uses of dimethenamid include its use for pre- or early post-emergence control of annual grass and broadleaf weeds, e.g., in maize, soybeans, sugar beet, potatoes, dry beans and other crops.
As used herein, fenoxasulfone is 3-[(2,5-dichoro-4-ethoxybenzyl)sulfonyl]-4,5- dihydro-5,5-dimethyl-l,2-oxazole and possesses the following structure:
Figure imgf000015_0003
Exemplary uses of fenoxasulfone include its use in rice for control of barnyardgrass, annual broadleaf weeds, and needle spike rush.
As used herein, fentrazamide is 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5- dihydro-5-oxo-lH-tetrazole-l-carboxamide and possesses the following structure:
Figure imgf000016_0001
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of fentrazamide include its use for control of barnyard grass (Echinochloa spp.) and annual sedges, from weed pre-emergence, e.g., in rice.
As used herein, flufenacet is N-(4-fluorophenyl)-N-(l-methylethyl)-2-[[5- (trifluoromethyl)-l,3,4-thiadiazol-2-yl]oxy]acetamide and possesses the following structure:
Figure imgf000016_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of flufenacet include its use for broad-spectrum grass control and control of broadleaf weeds.
As used herein, indanofan is (RS)-2-[[2-(3-chlorophenyl)oxiranyl]methyl]-2-ethyl- lH-indene-l,3(2H)-dione and possesses the following structure:
Figure imgf000016_0003
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of indanofan include its use for pre-emergence and post-emergence weed control, e.g., in transplanted rice, and pre-emergence weed control in turf.
As used herein, mefenacet is 2-(2-benzothiazolyloxy)-N-methyl-N-phenylacetamide and possesses the following structure:
Figure imgf000017_0001
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of mefenacet include its use for pre-emergence and early post-emergence control of grass weeds, e.g., in transplanted rice.
As used herein, S-metolachlor is a mixture of 2-chloro-N-(2-ethyl-6-methylphenyl)- N-[(15)-2-methoxy-l-methylethyl]acetamide and 2-chloro-N-(2-ethyl-6-methylphenyl)-N- [(lR)-2-methoxy-l-methylethyl]acetamide, wherein the mixture contains predominantly S- isomer, e.g., 80-100%. Metolachlor has the following formula:
Figure imgf000017_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of S-metolachlor include its use for control of annual grasses and broadleaf weeds, e.g., in maize, sorghum, cotton, sugar beet, fodder beet, sugar cane, potatoes, peanuts, soybeans, safflowers, sunflowers, various vegetables, fruit and nut trees, and woody ornamentals.
As used herein, molinate is S-ethyl hexahydro-lH-azepine-l-carbothioate and possesses the following structure:
Figure imgf000017_0003
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of molinate include its use for control of germinating broadleaf and grass weeds, e.g., in rice.
As used herein, pethoxamid is 2 -Chloro-N-(2-ethoxyethyl)-N-(2 -methyl- 1 -phenyl- 1- propen-l-yl)acetamide and possesses the following structure:
Figure imgf000018_0001
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pethoxamid include its use for pre-emergence to early post-emergence control i Echinochloa, Digitaria, Setaria, Amaranthus and Chenopodium spp., and other monocotyledonous and annual broadleaf weeds, e.g., in corn/maize, oilseed rape and soybeans.
As used herein, pretilachlor is 2-chloro-N-(2,6-diethylphenyl)-N-(2- propoxyethyl)acetamide and possesses the following structure:
Figure imgf000018_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of pretilachlor include its use for control of annual grasses, broadleaf weeds and sedges, e.g., in transplanted and seeded rice.
As used herein, prosulfocarb is ^-(phenylmethyl) dipropylcarbamothioate and possesses the following structure:
Figure imgf000018_0003
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of prosulfocarb include its use for pre- and early post-emergence control of grass and broadleaf weeds, e.g., in winter wheat, winter barley and rye.
As used herein, pyroxasulfone is 3-[[[5-(difluoromethoxy)-l-methyl-3- (trifluoromethyl)- lH-pyrazol-4-yl]methyl]sulfonyl]-4,5-dihydro-5,5-dimethylisoxazole and possesses the following structure:
Figure imgf000019_0001
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Pyroxasulfone provides, e.g., pre-emergence control of annual grasses and some broadleaf weeds in maize, soybeans, wheat and other crops.
As used herein, thenylchlor is 2-chloro-N-(2,6-dimethylphenyl)-N-[(3-methoxy-2- thienyl)methyl]acetamide and possesses the following structure:
Figure imgf000019_0002
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of thenylchlor include its use for pre-emergence control of annual grass and broadleaf weeds, e.g., in paddy rice.
As used herein, thiobencarb is 5'-[(4-chlorophenyl)methyl] N,N-diethylcarbamothioate and possesses the following structure:
Figure imgf000019_0003
Its herbicidal activity is exemplified in The Pesticide Manual, Fifteenth Edition, 2009. Exemplary uses of thiobencarb include its use for pre-emergence to early post-emergence control of Echinochloa, Leptochloa and Cyperus spp., and other monocotyledonous and annual broadleaf weeds, e.g., in direct-seeded and transplanted rice.
As used herein, herbicide means a compound, e.g., active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
As used herein, a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect to the vegetation e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.
As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation.
Described herein are methods of controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, as well as pre-emergence, post-emergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged vegetation, broadcast, spot, mechanical, water- injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods.
As used herein, plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula: R1R2R3R4N+
wherein R1, R2, R3 and R4 each, independently represents hydrogen or d-C12 alkyl, C3-C12 alkenyl or C3-C12 alkynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that R1, R2, R3 and R4 are sterically compatible. Additionally, any two of R1, R2, R3 and R4 together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from C1-C12 alkyl, C3-C12 alkenyl, C3-C12 alkynyl or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or unsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or C1-C4 alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
COMPOSITIONS AND METHODS
Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000021_0001
or an agriculturally acceptable salt or ester of thereof, and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides. In some embodiments, the VLCFA or fatty acid/lipid synthesis inhibiting herbicide is acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s- metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or a salt thereof.
Provided herein are also methods of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof, i.e., the area adjacent to the vegetation with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of formula (I) or salt of ester thereof and (b) VLCFA or fatty acid/lipid synthesis inhibiting herbicides. In certain embodiments, the methods employ the compositions described herein.
Furthermore, in some embodiments, the combination of compound (I) or
agriculturally acceptable salt or ester thereof and VLCFA or fatty acid/lipid synthesis inhibiting herbicides, or an agriculturally acceptable salt or ester thereof exhibits synergism, e.g., the herbicidal active ingredients are more effective in combination than when applied individually. Synergism has been defined as "an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately." Senseman, S., ed. Herbicide Handbook. 9th ed. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by the Colby's equation. Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.
In certain embodiments of the compositions and methods described herein, the compound of formula (I), i.e., the carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl, substituted benzyl, or Ci-4 alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.
In some embodiments, the compound of formula (I) or salt or ester thereof and acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb, or an agriculturally acceptable salt thereof are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodiments, the compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature undesirable vegetation to achieve the maximum control of weeds.
In some embodiments, the compositions and methods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights-of-way (ROW).
In certain embodiments, the compositions and methods provided herein are utilized to control weeds in rice. In certain embodiments, the rice is direct-seeded, water-seeded, or transplanted rice.
The compositions and methods described herein may be used to control undesirable vegetation in glyphosate-tolerant-, 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicamba- tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl- pyruvate dioxygenase (HPPD) inhibitor-tolerant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor- tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem II inhibitor- tolerant-, triazine-tolerant-, bromoxynil-tolerant- crops (such as, but not limited to, soybean, cotton, canola/oilseed rape, rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc.), for example, in conjunction with glyphosate, EPSP synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones,
phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas,
pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil. The compositions and methods may be used in controlling undesirable vegetation in crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or inhibitors of multiple modes of action. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other
complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or sequentially.
The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
The compositions and methods provided herein are utilized to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in direct-seeded, water-seeded, and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, ornamental species, aquatics, plantation crops, vegetables, industrial vegetation management (rVM) and rights of way (ROW).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA),
Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass,
ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa oryzicola (Vasinger) Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice barnyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Oryza species (red and weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir. (dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus difformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus Rottb. /C.B.Clarke (tidalmarsh flatsedge, CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Schoenoplectus species (SCPSS),
Schoenoplectus juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L. (ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago- aquatica L. (common waterplantain, ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETLI), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDLI), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria,
MOOKA), Monochoria vaginalis (Burm. F.) C. Presl ex Kuhth, (monochoria, MOOVA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY), Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Rotala indica (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv. (windgrass, APESV), Avena fatua L. (wild oat, AVEFA), Bromus tectorum L. (downy brome, BROTE), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Phalaris minor Retz. (littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POA ), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow foxtail, SETLU), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Amaranthus retroflexus L. (redroot pigweed, AMARE), Brassica species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Galium aparine L. (catchweed bedstraw, GALAP), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lamium purpureum L. (purple deadnettle , LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MATMT), Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SI SS), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR). In some embodiments, the methods provided herein are utilized to control undesirable vegetation in range and pasture, fallowland, IVM and ROW. In certain embodiments, the undesirable vegetation is Ambrosia artemisiifolia L. (common ragweed, AMBEL), Cassia obtusifolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted knapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Convolvulus arvensis L. (field bindweed, CONAR), Daucus carota L. (wild carrot, DAUCA), Euphorbia esula L. (leafy spurge, EPHES), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhorn plantain, PLALA), Rumex obtusifolius L. (broadleaf dock,
RUMOB), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Urtica dioica L. (common nettle, URTDI).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation found in row crops, tree and vine crops and perennial crops. In certain
embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decumbens (Stapf) R.D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hochst. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R.D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC), Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, TRCIN), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (barnyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine indica (L.) Gaertn.
(goosegrass, ELEIN), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (fall panicum, PANDI), Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrm. (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVI), Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus rotundus L. (purple nutsedge, CYPRO), Abutilon theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC.
(western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buttonweed, BOILF), Spermacose latifolia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L. (tropical spiderwort, COMBE), Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA), Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPHDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane, ERICA), Conyza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), Jacquemontia tamnifolia (L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq. (ivyleaf morningglory, IPOHE), Ipomoea lacunosa L. (white morningglory, IPOLA), Lactuca serriola L./Torn. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCHSS), Sida species (sida, SIDSS), Sida spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SI AR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turf. In certain embodiments, the undesirable vegetation is Bellis perennis L. (English daisy, BELPE), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus species (CYPSS), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Diodia virginiana L. (Virginia buttonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L. (ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicaule L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L. (broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhorn/narrowleaf plantain,
PLALA), Phyllanthus urinaria L. (chamberbitter, PYLTE), Rumex obtusifolius L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers
(dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).
In some embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation consisting of grass, broadleaf and sedge weeds. In certain embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation including Brachiaria, Brassica, Chenopodium, Cirsium, Cyperus, Digitaria, Echinochloa, Fimbristylis, Galium, Ipomoea, Ischaemum, Kochia, Leptochloa, Papaver, Polygonum, Salsola, Schoenoplectus, Sinapis, Stellaria and Xanthium.
In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and VLCFA and fatty acid/lipid synthesis inhibiting herbicides or agriculturally acceptable salt or ester thereof is used to control Brachiaria platyphylla (Griseb.) Nash or Urochloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Brassica napus L. (winter oilseed rape, BRSNW), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop, (large crabgrass, DIGSA), Echinochloa crus-galli (L.) Beauv. (barnyardgrass, ECHCG), Echinochloa colona (L.) Link, (junglerice, ECHCO), Echinochloa oryzoides (Ard.) Fritsch (early watergrass, ECHOR), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI), Galium aparine L. (catchweed bedstraw, GALAP), Ipomoea hederacea Jacq. (ivyleaf morningglory, IPOHE), Ischaemum rugosum
Salisb. (saramollagrass, ISCRU), Kochia scoparia (L.) Schrad. (kochia, KCHSC), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCH) Papaver rhoeas L. (common poppy, PAPRH), Polygonum hydropiperoides Michx. (POLHP, mild smartweed), Salsola tragus L. (Russian thistle, SASKR), Schoenoplectus juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Sinapis arvensis L. (wild mustard, SINAR), Stellaria media (L.) Vill. (common chickweed, STEME) and Xanthium strumarium L. (common cocklebur, XANST).
The compounds of formula I or agriculturally acceptable salt or ester thereof may be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a compound of formula I or agriculturally acceptable salt or ester thereof and the compositions described herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem II inhibitors (e.g., phenylcarbamates, pyridazinones, triazines, triazinones, uracils, amides, ureas,
benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines),, synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors (e.g., bipyridyliums), 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, bialafos), microtubule assembly inhibitors (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VLCFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitors (e.g., clomazone, amitrole, aclonifen), inhibitors, phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, furanones, phenoxybutan-amides, pyridiazinones, pyridines), 4- hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors (e.g., callistemones, isoxazoles, pyrazoles, triketones), mitosis inhibitors, cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocarboxamides), herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action, and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
In some embodiments, an agriculturally acceptable ester or salt of compound (I) is employed. In certain embodiments, an agriculturally acceptable ester is employed. In certain embodiments, the ester is a Ci_4 alkyl ester. In certain embodiments, the ester is a benzyl ester. In certain embodiments, compound (I), which is a carboxylic acid, is employed. In some embodiments, an agriculturally acceptable salt of acetochlor, alachlor, anilofos, butachlor, benfuresate, cafenstrole, dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor and thiobencarb is employed in the methods or compositions described herein.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with acetochlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 : 1680 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :46 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :90 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to acetochlor is within the range of from about 1 :46 to about 1 :5.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and acetochlor. In one embodiment, the composition comprises the compound of formula (I) and acetochlor, wherein the weight ratio of the compound of formula (I) to acetochlor is about 1 :46 to about 1 :5.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and acetochlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to acetochlor is about 1 :23 to about 1 :5.5. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 3,660 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and acetochlor, e.g., sequentially or simultaneously. In some embodiments, the acetochlor is applied at a rate from about 50 gai/ha to about 3360 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 grams acid equivalent per hectare (gae/ha) to about 300 gae/ha. In some embodiments, the acetochlor is applied at a rate from about 50 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the acetochlor is applied at a rate from about 100 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and acetochlor. In one embodiment, the methods utilize the compound of formula (I) and acetochlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and acetochlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and acetochlor is applied at a rate of about 50 gai/ha to about 200 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with acetochlor are used to control BRAPP, DIGSA, ECHCG, ECHOR, CYPRO, LEFCH or FIMMI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with alachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor is within the range of from about 1 :3350 to about 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor or salt or ester thereof is within the range of from about 1 : 1000 to about 1 :3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to alachlor or salt or ester thereof is within the range of from about 1 :39 to about 1 :78. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and alachlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 172 grams active ingredient per hectare (gai/ha) to about 7000 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 174 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1272 grams active ingredient per hectare (gai/ha) to about 2512 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and alachlor, e.g., sequentially or simultaneously. In some embodiments, the alachlor is applied at a rate from about 170 gai/ha to about 6700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and alachlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with alachlor are used to control IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with anilofos. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos or salt or ester thereof is within the range of from about 1 :250 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1 :45 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to anilofos is within the range of from about 1 :50 to about 1 :3. In certain
embodiments, the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and anilofos. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 750 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 54 grams active ingredient per hectare (gai/ha) to about 235 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and anilofos, e.g., sequentially or simultaneously. In some embodiments, the anilofos is applied at a rate from about 50 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the anilofos is applied at a rate from about 100 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and anilofos. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with anilofos are used to control ECHCG, ECHOR, CYPRO or FIMMI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with benfuresate.
With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :300 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 : 1 13 to about 1.33: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :70 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 : 70 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to benfuresate is within the range of from about 1 :57 to about 1 : 1.8. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and benfuresate. In one embodiment, the composition comprises the compound of formula (I) and benfuresate, wherein the weight ratio of the compound of formula (I) to benfuresate is about 1 :57 to about 1 : 1.8. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and benfuresate, wherein the weight ratio of the benzyl ester of the compound of formula (I) to benfuresate is about 1 :69 to about 1 :4. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 55 grams active ingredient per hectare (gai/ha) to about 242 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and benfuresate or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, benfuresate is applied at a rate from about 50 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the benfuresate is applied at a rate from about 25 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 200 gae/ha. In some embodiments, the benfuresate is applied at a rate from about 50 gai/ha to about 600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and benfuresate. In one embodiment, the methods utilize the compound of formula (I) and benfuresate, wherein the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and benfuresate is applied at a rate of about 75 gai/ha to about 300 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and benfuresate, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 5.3 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and benfuresate is applied at a rate of about 75 gai/ha to about 600 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with benfuresate are used to control ECHCG, ECHCO, LEFCH, CYPIR, POLHP, SCPJU or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with butachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 :750 to about 3 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 : 103 to about 1 :6. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 :200 to about 1 :3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to butachlor is within the range of from about 1 : 102 to about 1 :6. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or w-butyl ester and butachlor. In one embodiment, the composition comprises the compound of formula (I) and butachlor, wherein the weight ratio of the compound of formula (I) to butachlor is about 1 : 102 to about 1 :6. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and butachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to butachlor is about 1 : 102 to about 1 :6. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 115 grams active ingredient per hectare (gai/ha) to about 1800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 117 grams acid active ingredient per hectare (gai/ha) to about 468 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and butachlor, e.g., sequentially or simultaneously. In some embodiments, the butachlor is applied at a rate from about 113 gai/ha to about 1500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the butachlor or salt or ester thereof is applied at a rate from about 50 gai/ha to about 900 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the butachlor or salt or ester thereof is applied at a rate from about 112.5 gai/ha to about 450 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or w-butyl ester and butachlor. In one embodiment, the methods utilize the compound of formula (I) and butachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and butachlor is applied at a rate of about 112.5 gai/ha to about 450 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and butachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and butachlor is applied at a rate of about 1 12.5 gai/ha to about 450 gai/ha. In certain
embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with butachlor are used to control ECHCO, LEFCH, BRAPP, IPOHE, ECHCG, ECHOR, or CYPRO.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with cafenstrole. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 : 150 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 : 24 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 :50 to about 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cafenstrole is within the range of from about 1 :24 to about 1 : 1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and cafenstrole. In one embodiment, the composition comprises the compound of formula (I) and cafenstrole, wherein the weight ratio of the compound of formula (I) to cafenstrole is about 1 :24 to about 1 : 1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1 :24 to about 1 : 1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cafenstrole, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cafenstrole is about 1 :47 to about 2.7: 1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 30 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and cafenstrole, e.g., sequentially or simultaneously. In some embodiments, the cafenstrole is applied at a rate from about 26 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the cafenstrole is applied at a rate from about 10 gai/ha to about 200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the cafenstrole is applied at a rate from about 26.3 gai/ha to about 105 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and cafenstrole. In one embodiment, the methods utilize the compound of formula (I) and cafenstrole, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 105 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cafenstrole, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 70 gae/ha, and cafenstrole is applied at a rate of about 26.3 gai/ha to about 210 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cafenstrole are used to control BRAPP, ECHCG, ECHCO, LEFCH, IPOHE, CYPIR, ECHOR, SCPJU or CYPRO. In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with dimethenamid-P. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1 :850 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to dimethenamid-P is within the range of from about 1 :205 to about 1 :8. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 2,000 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 283 grams active ingredient per hectare (gai/ha) to about 1,670 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and dimethenamid-P, e.g., sequentially or simultaneously. In some embodiments, the dimethenamid-P is applied at a rate from about 280 gai/ha to about 1,700 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the dimethenamid-P is applied at a rate from about 275 gai/ha to about 1,640 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and dimethenamid-P are used to control ECHCO, CYPES, and XANST.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with fenoxasulfone. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxasulfone is within the range of from about 1 :250 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxasulfone is within the range of from about 1 :46 to about 1 : 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and fenoxasulfone. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 53 grams acid active ingredient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fenoxasulfone, e.g., sequentially or simultaneously. In some embodiments, the fenoxasulfone is applied at a rate from about 50 gai/ha to about 500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fenoxasulfone is applied at a rate from about 50 gai/ha to about 500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and fenoxasulfone.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with fentrazamide. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 150 to about 19: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 15 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 :68 to about 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 :32 to about 2: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fentrazamide is within the range of from about 1 : 16 to about 1 : 1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fentrazamide. In one embodiment, the composition comprises the compound of formula (I) and fentrazamide, wherein the weight ratio of the compound of formula (I) to fentrazamide is about 1 : 16 to about 1 : 1.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fentrazamide, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fentrazamide is about 1 : 19 to about 1 :2. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 18 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fentrazamide, e.g. , sequentially or simultaneously. In some embodiments, fentrazamide is applied at a rate from about 16 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fentrazamide is applied at a rate from about 7 gai/ha to about 140 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some
embodiments, the fentrazamide is applied at a rate from about 16.9 gai/ha to about 67.5 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fentrazamide. In one embodiment, the methods utilize the compound of formula (I) and fentrazamide, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and fentrazamide is applied at a rate of about 16.9 gai/ha to about 67.5 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fentrazamide, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and fentrazamide is applied at a rate of about 33.8 gai/ha to about 300 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with fentrazamide are used to control BRAPP, ECHCG, ECHCO, LEFCH, DIGSA, or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with flufenacet. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :625 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :68 to about 6: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to flufenacet is within the range of from about 1 :300 to about 1 :2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and flufenacet. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 1550 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the composition is applied at an application rate of from about 62 grams active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 28 grams active ingredient per hectare (gai/ha) to about 300 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and flufenacet, e.g., sequentially or simultaneously. In some embodiments, the flufenacet is applied at a rate from about 25 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the flufenacet is applied at a rate from about 60 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 32 gae/ha.In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and flufenacet. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with flufenacet are used to control BRAPP, CIRAR, CHEAL, KCHSC, PAPRH, SASKR, SINAR and STEME
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with indanofan. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1 : 150 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to indanofan is within the range of from about 1 : 136 to about 6: 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and indanofan. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 600 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 30 grams acid active ingredient per hectare (gai/ha) to about 450 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and indanofan, e.g., sequentially or simultaneously. In some embodiments, the indanofan is applied at a rate from about 25 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the indanofan is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and indanofan. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with indanofan are used to control ECHCO and LEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with mefenacet. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 :800 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 :727 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to mefenacet is within the range of from about 1 : 150 to about 1 :2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and mefenacet. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 252 grams active ingredient per hectare (gai/ha) to about 1900 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 255 grams acid active ingredient per hectare (gai/ha) to about 1750 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and mefenacet or salt thereof, e.g., sequentially or simultaneously. In some embodiments, the mefenacet is applied at a rate from about 250 gai/ha to about 1600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the mefenacet is applied at a rate from about 50 gai/ha to about 1200 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n- butyl ester and mefenacet. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with mefenacet are used to control BRAPP, LEFCH, CYPIR or ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with s-metolachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 1500 to about 4: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 1000 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to s-metolachlor is within the range of from about 1 : 194 to about 1 : 12. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and s-metolachlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 72 grams active ingredient per hectare (gai/ha) to about 3300 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 73 grams active ingredient per hectare (gai/ha) to about 2290 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and s-metolachlor, e.g., sequentially or simultaneously. In some embodiments, the s-metolachlor is applied at a rate from about 70 gai/ha to about 3000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the s-metolachlor is applied at a rate from about 387 gai/ha to about 1550 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and s-metolachlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-metolachlor are used to control ECHCG or IPOHE.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with molinate. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 :2780 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 :255 to about 1 :8. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to molinate is within the range of from about 1 : 194 to about 1 :44. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and molinate. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 282 grams active ingredient per hectare (gai/ha) to about 5860 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 284 grams active ingredient per hectare (gai/ha) to about 1155 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1408 grams active ingredient per hectare (gai/ha) to about 2832 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and molinate, e.g., sequentially or simultaneously. In some embodiments, the molinate is applied at a rate from about 280 gai/ha to about 5560 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the molinate is applied at a rate from about 1400 gai/ha to about 2800 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and molinate. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with s-molinate are used to control ECHOR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pethoxamid.
With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1 :625 to about 1.5: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pethoxamid is within the range of from about 1 : 150 to about 1 : 10. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pethoxamid. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 202 grams active ingredient per hectare (gai/ha) to about 1,550 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 313 grams acid active ingredient per hectare (gai/ha) to about 1,252 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pethoxamid, e.g., sequentially or simultaneously. In some embodiments, the pethoxamid is applied at a rate from about 200 gai/ha to about 1,250 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pethoxamid is applied at a rate from about 305 gai/ha to about 1,220 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester in combination with pethoxamid are used to control IPOHE, LEFCH, CYPES or CYPIR.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pretilachlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :375 to about 8: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :34 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 : 64 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :32 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pretilachlor is within the range of from about 1 :91 to about 2.7: 1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and pretilachlor. In one embodiment, the composition comprises the compound of formula (I) and pretilachlor, wherein the weight ratio of the compound of formula (I) to pretilachlor is about 1 :34 to about 1 :2. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1 :32 to about 1 :4. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and pretilachlor, wherein the weight ratio of the benzyl ester of the compound of formula (I) to pretilachlor is about 1 :91 to about 2.7: 1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 40 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 43 grams active ingredient per hectare (gai/ha) to about 500 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pretilachlor, e.g., sequentially or simultaneously. In some embodiments, the pretilachlor is applied at a rate from about 38 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 18 gai/ha to about 300 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 37.5 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In some embodiments, the pretilachlor is applied at a rate from about 37.5 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and pretilachlor. In one embodiment, the methods utilize the compound of formula (I) and pretilachlor, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 150 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and pretilachlor, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 100 gae/ha, and pretilachlor is applied at a rate of about 37.5 gai/ha to about 400 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pretilachlor are used to control BRAPP, ECHCO, DIGSA, CYPIR, ECHCG, ECHOR, CYPRO, FIMMI, or SCPJU.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with prosulfocarb. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 :2000 to about 1 : 1.5. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 : 1818 to about 1 : 10. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to prosulfocarb is within the range of from about 1 : 1600 to about 1 : 100. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n- butyl ester and prosulfocarb. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 502 grams active ingredient per hectare (gai/ha) to about 4300 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 510 grams acid active ingredient per hectare (gai/ha) to about 4050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 1,002 grams acid active ingredient per hectare (gai/ha) to about 4010 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and prosulfocarb, e.g., sequentially or simultaneously. In some embodiments, the prosulfocarb is applied at a rate from about 500 gai/ha to about 4000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the prosulfocarb is applied at a rate from about 1 ,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.0 gae/ha to about 100 gae/ha. In some embodiments, the prosulfocarb is applied at a rate from about 1,000 gai/ha to about 4,000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2.5 gae/ha to about 10 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and prosulfocarb. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with prosulfocarb are used to control BRSNW, CHEAL, GALAP, KCHSC, PAPRH, SASKR, SINAR and STEME.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pyroxasulfone. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1 :200 to about 12: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pyroxasulfone is within the range of from about 1 : 15 to about 1 : 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 27 grams active ingredient per hectare (gai/ha) to about 700 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 37 grams acid active ingredient per hectare (gai/ha) to about 150 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pyroxasulfone, e.g., sequentially or simultaneously. In some embodiments, the pyroxasulfone is applied at a rate from about 25 gai/ha to about 400 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the pyroxasulfone is applied at a rate from about 30 gai/ha to about 120 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pyroxasulfone. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with pyroxasulfone are used to control ECHCG or BRAPP.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with thenylchlor. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :375 to about 4: 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :341 to about 1 : 1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thenylchlor is within the range of from about 1 :34 to about 1 : 1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 77 grams active ingredient per hectare (gai/ha) to about 1050 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 79 grams acid active ingredient per hectare (gai/ha) to about 800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 143 grams acid active ingredient per hectare (gai/ha) to about 302 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thenylchlor, e.g., sequentially or simultaneously. In some embodiments, the thenylchlor is applied at a rate from about 75 gai/ha to about 750 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the thenylchlor is applied at a rate from about 135 gai/ha to about 270 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 8 gae/ha to about 32 gae/ha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and thenylchlor. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thenychlor or salt or ester thereof are used to control ECHOR and LEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with thiobencarb. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :2250 to about 1 :2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :51 1 to about 1 :32. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :510 to about 1 : 17. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 : 1000 to about 1 : 16. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to thiobencarb is within the range of from about 1 :511 to about 1 :32. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and thiobencarb. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 : 16. In one embodiment, the composition comprises the compound of formula (I) and thiobencarb, wherein the weight ratio of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 :32. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and thiobencarb, wherein the weight ratio of the benzyl ester of the compound of formula (I) to thiobencarb is about 1 :511 to about 1 :64. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 562 grams active ingredient per hectare (gai/ha) to about 4,800 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 564 grams active ingredient per hectare (gai/ha) to about 2275 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and thiobencarb, e.g., sequentially or simultaneously. In some embodiments, the thiobencarb is applied at a rate from about 560 gai/ha to about 4500 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the thiobencarb is applied at a rate from about 280 gai/ha to about 5000 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the thiobencarb is applied at a rate from about 560 gai/ha to about 2240 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and thiobencarb. In one embodiment, the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In one embodiment, the methods utilize the compound of formula (I) and thiobencarb, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and thiobencarb, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.83 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and thiobencarb is applied at a rate of about 560 gai/ha to about 2240 gai/ha. In certain embodiments, the methods and
compositions utilizing the compound of formula (I) or salt or ester thereof in combination with thiobencarb or salt or ester thereof are used to control ECHOR, CYPRO, DIGSA, CYPIR, ISCRU or ECHCO.
The components of the mixtures described herein can be applied either separately or as part of a multipart herbicidal system.
The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA; 4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB; 2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-T; 2,4,5-TB; acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, bensulfuron- methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiazuron, bialaphos,
bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben,
chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodinafop-propargyl, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron,
dimepiperate, dimethachlor, dimethametryn, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P-ethyl, fenoxaprop-P-ethyl + isoxadifen-ethyl, fenoxasulfone, fenteracol, fenthiaprop, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazifop, fluazifop-P-butyl, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenican, flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac- pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifen-methyl, halosafen, halosulfuron-methyl, haloxydine, haloxyfop-methyl, haloxyfop-P -methyl, hexachloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA- thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ort/zodichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, phenisopham, phenmedipham, phenmedipham- ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, prohexadione-calcium, prometon, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrazogyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P-ethyl, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, sethoxydim, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, SY -523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone- methyl, thifensulfuron, thifensulfurn-methyl, tiocarbazil, tioclorim, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr choline salt, triclopyr esters and salts, tridiphane, trietazine,
trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, esters, optically active isomers and mixtures thereof.
The compositions and methods described herein, can further be used in conjunction with glyphosate, 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitors, glufosinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines,
sulfonylaminocarbonyltriazolinones, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil on glyphosate- tolerant, EPSP synthase inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone- tolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant, PPO- tolerant, cellulose biosynthesis inhibitor-tolerant, mitosis inhibitor-tolerant, microtubule inhibitor-tolerant, very long chain fatty acid inhibitor-tolerant, fatty acid and lipid biosynthesis inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem II inhibitor- tolerant, triazine-tolerant, and bromoxynil-tolerant crops, and crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or multiple modes of action via single and/or multiple resistance mechanisms. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other
complementary herbicides are applied at the same time, either as a combination formulation, as a tank mix, or as a sequential application.
In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safeners are employed in rice, cereal, corn, or maize settings. In some embodiments, the safener is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).
In some embodiments, the compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide, a-naphthaleneacetic acids, benzyladenine, 4- hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, prohexadione, triapenthenol and trinexapac.
In some embodiments, the plant growth regulators are employed in one or more crops or settings, such as rice, cereal crops, corn, maize, broadleaf crops, oilseed rape/canola, turf, pineapple, sugarcane, sunflower, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, plantation crops, vegetables, and non-crop (ornamentals) settings. In some embodiments, the plant growth regulator is mixed with the compound of formula (I), or mixed with the compound of formula (I) and VLCFA inhibitors or fatty acid/lipid synthesis inhibitors to cause a preferentially advantageous effect on plants.
In some embodiments, compositions provided herein further comprise at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a pre-mix or tank mixed.
Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; Cg-Cn alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (Cu-Cw) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap;
nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate- 99.
Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, w-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, Water is the carrier for the dilution of concentrates.
Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the present formulations are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in "Encyclopedia of Surfactants," Vol. I-III, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate;
alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-Cis ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-Ci6 ethoxylate; soaps, such as sodium stearate; alkyl- naphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
Other exemplary additives for use in the compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants,
antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
In some embodiments, the concentration of the active ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrates, the active ingredients, in certain embodiments, are present in a concentration from about 0.1 to 98 weight percent, and in certain embodiment's about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingredient and in certain embodiments contain about 0.01 to 7.0 weight percent.
The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
The described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter. Examples
Results in Examples I, II, III, and IV are greenhouse trial results.
Example I. Evaluation of Postemergence Foliar- Applied Herbicidal Mixtures for Weed
Control in Direct Seeded Rice
Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters Excel® 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis.
Supplemental lighting was provided with overhead metal halide 1000- Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:
Figure imgf000061_0001
Compound A Acid
Figure imgf000062_0001
Compound A Benzyl Ester
Other herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis- inhibiting herbicides acetochlor (technical grade material), acetochlor + dichlormid formulated as Topnotch®, pretilachlor (technical grade material), butachlor formulated as Butachlor EC, fentrazamide formulated as Fentrazamide EC, thiobencarb formulated as Bolero® 8EC, cafenstrole formulated as Himeadow® WP or Lapost® Flowable, benfuresate formulated as Full Shot®, dimethenamid-P formulated as Outlook®, indanofan (technical grade material), flufenacet formulated as Define® DF, mefenacet (technical grade material), S-metolachlor formulated as Dual® II Magnum, pethoxamid formulated as Successor® 600, and pyroxasulfone (technical grade material).
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.
For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrated to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g. , 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After
approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill. Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 1-25.
Table 1. Synergistic Activity of Foliar- Applied Compound A Acid and Acetochlor Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000064_0001
0 200 20 -
4.38 100 50 44
17.5 100 75 52
4.38 200 60 44
17.5 200 80 52
Table 2. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Acetochlor Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000065_0001
Table 3. Synergistic Activity of Foliar- Applied Compound A Acid and Acetochlor + Dichlormid Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000066_0001
Figure imgf000066_0002
gai/ha refers to active ingredient of acetachlor.
Table 4. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Acetochlor + Dichlormid Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000067_0001
gai/ha refers to active ingredient of acetachlor.
Table 5. Synergistic Activity of Foliar- Applied Compound A Acid and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000067_0002
4.38 0 50 - 65 -
8.75 0 70 - 85 -
0 37.5 0 - 0 -
0 75 0 - 0 -
0 150 0 - 0 -
4.38 37.5 65 50 95 65
8.75 37.5 80 70 90 85
4.38 75 65 50 85 65
8.75 75 70 70 95 85
4.38 150 70 50 95 65
8.75 150 90 70 90 85
Figure imgf000068_0001
Table 6. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000069_0001
Figure imgf000069_0002
4.38 37.5 95 80
4.38 75 100 80
Table 7. Synergistic Activity of Foliar- Applied Compound A Acid and Butachlor Herbicidal
Compositions on Weed Control in a Rice Cropping System.
Figure imgf000070_0001
17.5 0 30 -
0 112.5 0 -
0 225 0 -
0 450 0 -
4.38 112.5 10 0
8.75 112.5 20 10
17.5 112.5 65 30
4.38 225 NT 0
8.75 225 30 10
17.5 225 60 30
4.38 450 75 0
8.75 450 50 10
17.5 450 85 30
Figure imgf000071_0001
Table 8. Synergistic Activity of Foliar- Applied Compound A Benzyl and Butachlor
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000071_0002
4.38 225 65 60 80 60
8.75 225 80 65 85 70
4.38 450 70 60 80 60
8.75 450 95 65 80 70
Figure imgf000072_0001
Compound Visual Weed
A Benzyl Butachlor Control (%) - 20
Ester DAA
IPOHE
gae/ha gai/ha Obs Exp
4.38 0 10 -
8.75 0 15 -
17.5 0 25 -
0 112.5 20 -
0 450 30 -
4.38 112.5 60 28
8.75 112.5 25 32
17.5 112.5 80 40
4.38 450 70 37
8.75 450 70 41
17.5 450 25 48 Table 9. Synergistic Activity of Foliar- Applied Compound A Acid and Fentrazamide Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000073_0001
Figure imgf000073_0002
0 67.5 0 -
4.38 33.75 10 15
8.75 33.75 50 30
17.5 33.75 60 50
4.38 67.5 30 15
8.75 67.5 40 30
17.5 67.5 65 50
Table 10. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Fentrazamide Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000074_0001
Table 11. Synergistic Activity of Foliar- Applied Compound A Acid and Thiobencarb Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000075_0001
Table 12. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Thiobencarb Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000075_0002
Compound Visual Weed
A Benzyl Thiobencarb Control (%) - 21
Ester DAA
ISCRU
gae/ha gai/ha Obs Exp
8 0 20 -
16 0 0 -
0 1120 0 -
0 2240 0 -
8 1120 0 20
16 1120 85 0
8 2240 100 20
16 2240 100 0
Table 13. Synergistic Activity of Foliar- Applied Compound A Acid and Cafenstrole (Himeadow® WP) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000076_0001
8.75 26.25 75 64
4.38 52.5 60 46
8.75 52.5 85 64
4.38 105 75 46
8.75 105 90 64
Figure imgf000077_0001
Table 14. Synergistic Activity of Foliar- Applied Compound A Acid and Cafenstrole (Lapost Flowable) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000078_0001
Figure imgf000078_0002
Table 15. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Cafenstrole (Himeadow® WP) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000078_0003
Compound Visual Weed
A Benzyl Cafenstrole Control (%) - 20
Ester DAA
LEFCH
gae/ha gai/ha Obs Exp
4.38 0 0 -
8.75 0 10 -
17.5 0 25 -
0 26.25 0 -
0 52.5 0 -
0 105 0 -
4.38 26.25 20 0
8.75 26.25 30 10
17.5 26.25 35 25
4.38 52.5 25 0
8.75 52.5 20 10
17.5 52.5 35 25
4.38 105 20 0
8.75 105 25 10
17.5 105 50 25
Compound Visual Weed
A Benzyl Cafenstrole Control (%) - 20
Ester DAA
IPOHE
gae/ha gai/ha Obs Exp
17.5 0 25 -
0 26.25 0 -
0 105 30 -
17.5 26.25 50 25
17.5 105 90 48
Table 16. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Cafenstrole (Lapost® Flowable) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000079_0001
8.75 0 10 -
17.5 0 30 -
0 26.25 0 -
4.38 26.25 20 0
8.75 26.25 40 10
17.5 26.25 45 30
Figure imgf000080_0001
Table 17. Synergistic Activity of Foliar- Applied Compound A Acid and Benfuresate Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000080_0002
0 300 0 - 0 -
5.3 75 65 65 80 65
10.6 75 80 55 80 65
5.3 150 75 65 85 65
10.6 150 90 55 85 65
5.3 300 90 65 85 65
10.6 300 90 55 90 65
Figure imgf000081_0001
Table 18. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Benfuresate Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000081_0002
0 150 0 - 0 -
0 300 0 - 0 -
4.38 75 40 40 55 30
8.75 75 55 60 60 55
4.38 150 65 40 85 30
8.75 150 85 60 70 55
4.38 300 85 40 75 30
8.75 300 90 60 85 55
Compound Visual Weed
A Benzyl Benfuresate Control (%) - 22
Ester DAA
LEFCH
gae/ha gai/ha Obs Exp
4.38 0 0 -
8.75 0 20 -
17.5 0 35 -
0 75 0 -
0 150 10 -
0 300 10 -
4.38 75 40 0
8.75 75 40 20
17.5 75 75 35
4.38 150 20 10
8.75 150 60 28
17.5 150 80 42
4.38 300 70 10
8.75 300 40 28
17.5 300 70 42
Table 19. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Dimethenamid-P Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000082_0001
16 275 95 88
32 275 95 97
Figure imgf000083_0001
Table 20. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Flufenacet Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000083_0002
Table 21. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Indanofan Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000084_0001
Table 22. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Mefenacet Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000084_0002
16 50 90 80
32 50 85 85
8 100 75 65
16 100 90 80
32 100 99 85
8 200 80 65
16 200 90 80
32 200 90 85
Compound Visual Weed
A Benzyl Mefenacet Control (%) - 22
Ester DAA
LEFCH
gae/ha gai/ha Obs Exp
8 0 35 -
16 0 40 -
0 50 10 -
0 100 0 -
8 50 20 42
16 50 60 46
8 100 55 35
16 100 40 40
Figure imgf000085_0001
Table 23. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and S- Metolachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000085_0002
8 0 63 -
16 0 78 -
32 0 83 -
0 387.5 20 -
0 775 55 -
8 387.5 95 70
16 387.5 95 82
32 387.5 95 86
8 775 90 83
16 775 95 90
32 775 95 92
Table 24. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Pethoxamid Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000086_0001
Figure imgf000086_0002
Table 25. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and
Pyroxasulfone Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000087_0001
Compound Visual Weed
A Benzyl Pyroxasulfone Control (%) - Ester 22 DAA
ECHCG
gae/ha gai/ha Obs Exp
8 0 25 -
16 0 50 -
32 0 85 -
0 59 70 -
8 59 90 78
16 59 85 85
32 59 99 96
BRAPP Urochloa platyphylla (Nash) R.D. Webster
or Brachiaria platyphylla (Griseb.) Nash signalgrass, broadleaf CYPIR Cyperus iria L. flatsedge, rice
CYPES Cyperus esculentus L. nutsedge, yellow
DIGSA Digitaria sanguinalis (L.) Scop. crabgrass, large ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass ECHCO Echinochloa colona (L.) Link junglerice
IPOHE Ipomoea hederacea Jacq. morningglory, ivyleaf
ISCRU Ischaemum rugosum Salisb. saramollagrass
LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese
SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese
gae/ha = grams acid equivalent per hectare
gai/ha = j grams active ingredient per hectare
Obs = observed value
Exp = expected value as calculated by Colby's equation
DAA = days after application
NT = not tested
Example II. Evaluation of In- Water Applied Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice
Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized mineral soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1 : 1 volumetric ratio. The prepared mud was dispensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm2) leaving a headspace of 3 centimeters (cm) in each pot. Mud was allowed to dry overnight prior to planting or transplanting. Rice seeds were planted in Sun
Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 840 mL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm2 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29 C during the day and 26°C during the night. Nutrients were added as Osmocote® (19:6: 12, N:P:K + minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) each formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination. Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:
Figure imgf000089_0001
Compound A Benzyl Ester
The herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis-inhibiting herbicides acetochlor (technical grade material), acetochlor + dichlormid formulateded as Topnotch®, pretilachlor (technical grade material), butachlor formulated as Butachlor EC, fentrazamide formulated as Fentrazamide EC, thiobencarb formulated as Bolero® 8EC, cafenstrole formulated as Himeadow® WP or Lapost® Flowable, benfuresate formulated as Full Shot®, anilofos (technical grade material), mefenacet (technical grade material), molinate (technical grade material), and thenylchlor (technical grade material). Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, an application volume of 2 mL per component per pot, and an application area of 86.59 cm2 per pot.
For formulated compounds, a measured amount was placed in an individual 100 or
200 mL glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate to obtain application solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.
For technical grade compounds, a weighed amount was placed in an individual 100 to 200 mL glass vial and was dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with an equivalent volume of an aqueous mixture containing 2.5% (v/v) crop oil concentrate so that the final application solutions contained 1.25% (v/v) crop oil concentrate.
Applications were made by injecting with a pipetter appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that all treated plant material received the same concentrations of acetone and crop oil concentrate.
The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingredient A at the same concentration as used in the mixture. B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 26-48.
Table 26. Synergistic Activity of In- Water Applications of Compound A Acid and
Acetochlor Herbicidal Compositions on Control of Weeds Common to Rice Cropping
Systems.
Figure imgf000091_0001
Figure imgf000091_0002
Figure imgf000091_0003
8.75 0 0 -
17.5 0 70 -
0 100 20 -
0 200 75 -
8.75 100 100 20
17.5 100 100 76
8.75 200 100 75
17.5 200 99 93
Table 27. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Acetochlor Herbicidal Compositions on Control of Weeds Common to Rice Cropping
Systems.
Figure imgf000092_0001
Figure imgf000092_0002
Figure imgf000092_0003
- 20 DAA
FIMMI
gae/ha gai/ha Obs Exp
4.38 0 30 -
8.75 0 60 -
0 100 80 -
0 200 20 -
4.38 100 100 86
8.75 100 100 92
4.38 200 100 44
8.75 200 100 68
Table 28. Synergistic Activity of In- Water Applications of Compound A Acid and Acetochlor + Dichlormid Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000093_0002
*gai/ha refers to active ingredient of acetachlor.
Table 29. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Acetochlor + Dichlormid Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Figure imgf000093_0001
Ester - 20 DAA
CYPRO
gae/ha gai/ha* Obs Exp
4.38 0 70 -
8.75 0 30 -
0 100 0 -
0 200 70 -
4.38 100 99 70
8.75 100 100 30
4.38 200 100 91
8.75 200 100 79
gai/ha refers to active ingredient of acetachlor.
Table 30. Synergistic Activity of In- Water Applications of Compound A Acid and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000094_0001
Figure imgf000094_0002
Table 31. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Pretilachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000095_0001
Figure imgf000095_0002
Table 32. Synergistic Activity of In- Water Applications of Compound A Acid and Butachlor
Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000095_0003
8.75 0 0 - 30 -
17.5 0 0 - 25 -
35 0 20 - 30 -
0 225 40 - 0 -
0 450 20 - 20 -
8.75 225 20 40 85 30
17.5 225 40 40 95 25
35 225 95 52 95 30
8.75 450 50 20 70 44
17.5 450 60 20 99 40
35 450 95 36 99 44
Figure imgf000096_0001
Table 33. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Butachlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000096_0002
Figure imgf000097_0001
Table 34. Synergistic Activity of In- Water Applications of Compound A Acid and Fentrazamide Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000097_0002
Table 35. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Fentrazamide Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000097_0003
8.75 50 85 63
17.5 50 95 80
Table 36. Synergistic Activity of In- Water Applications of Compound A Acid and Thiobencarb Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000098_0001
Table 37. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Thiobencarb Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000098_0002
Figure imgf000098_0003
Figure imgf000099_0001
Table 38. Synergistic Activity of In- Water Applications of Compound A Acid and
Cafenstrole (Himeadow® WP) Herbicidal Compositions on Weed Control in a Rice Cropping
System.
Figure imgf000099_0002
Table 39. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Cafenstrole (Himeadow® WP) Herbicidal Compositions on Weed Control in a Rice Cropping
System.
Figure imgf000099_0003
gae/ha gai/ha Obs Exp Obs Exp
4.38 0 15 - 0 -
8.75 0 20 - 15 -
17.5 0 75 - 10 -
0 52.5 20 - 10 -
0 105 25 - 30 -
4.38 52.5 95 32 50 10
8.75 52.5 95 36 100 24
17.5 52.5 100 80 100 19
4.38 105 60 36 85 30
8.75 105 99 40 100 41
17.5 105 100 81 99 37
Compound Visual Weed
A Benzyl Cafenstrole Control (%) - 21
Ester DAA
CYPRO
gae/ha gai/ha Obs Exp
4.38 0 0 -
8.75 0 30 -
0 52.5 0 -
0 105 0 -
4.38 52.5 0 0
8.75 52.5 90 30
4.38 105 20 0
8.75 105 80 30
Table 40. Synergistic Activity of In- Water Applications of Compound A Acid and Cafenstrole (Lapost® Flowable) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000100_0001
35 52.5 95 75
Figure imgf000101_0001
Table 41. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Cafenstrole (Lapost® Flowable) Herbicidal Compositions on Weed Control in a Rice
Cropping System.
Figure imgf000101_0002
17.5 52.5 99 78
Figure imgf000102_0001
Table 42. Synergistic Activity of In- Water Applications of Compound A Acid and Benfuresate (Full Slot®) Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000102_0002
21.2 150 80 40
42.4 150 100 60
Table 43. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Benfuresate (Full Slot) Herbicidal Compositions on Weed Control in a Rice Cropping
System.
Figure imgf000103_0001
Table 44. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Anilofos Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000103_0002
32 0 40 -
0 100 20 -
8 100 20 44
16 100 95 36
32 100 99 52
Figure imgf000104_0001
Compound Visual Weed A Benzyl Anilofos Control (%) - 19 Ester DAA
FIMMI
gae/ha gai/ha Obs Exp
8 0 0 - 16 0 0 -
32 0 85 -
0 100 0 -
0 200 0 -
0 400 10 -
8 100 0 0
16 100 20 0
32 100 100 85
8 200 10 0
16 200 40 0
32 200 100 85
8 400 25 10
16 400 30 10
32 400 100 87
Table 45. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Indanofan Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000105_0001
Table 46. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Mefenacet Herbicidal Compositions on Weed Control in a Rice Cropping System. Compound Visual Weed
A Benzyl Mefenacet Control (%) - 21
Ester DAA
ECHOR
gae/ha gai/ha Obs Exp
8 0 75 -
16 0 95 -
32 0 100 -
0 300 80
0 600 100
0 1200 100
8 300 100 48
16 300 99 64
32 300 100 74
8 600 100 68
16 600 100 78
32 600 100 84
8 1200 100 84
16 1200 100 89
32 1200 100 92
Table 47. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Molinate Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000106_0001
Table 48. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester and Thenylchlor Herbicidal Compositions on Weed Control in a Rice Cropping System.
Figure imgf000107_0001
CYPRO Cyperus rotundus L. nutsedge, purple
ECHCG Echinochloa crusgalU (L.) Beauv. barnyardgrass
ECHOR Echinochloa oryzoides (Ard.) Fritsch watergrass, early
FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe
LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese
SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese
gae/ha = grams acid equivalent per hectare
gai/ha = \ jrams active ingredient per hectare
Obs = observed value
Exp = expected value as calculated by Colby's equation
DAA = days after application
Example III. Evaluation of Post-emergence Foliar- Applied Herbicidal Mixtures for Weed Control in Cereal Crops in the Greenhouse.
Seeds of the desired test plant species were planted in Sun Gro MetroMix® 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18° C during the day and 17° C during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000- Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC (suspension concentrate), and a second cereal herbicide alone and in combination.
Forms of compound A (compound of formula I) tested include:
Figure imgf000108_0001
Compound A Benzyl Ester
Measured aliquots of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-dex crop oil concentrated to obtain stock solutions. Compound requirements are based upon a 12 mL application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound mixtures were prepared by adding the stock solutions to the appropriate amount of dilution solution to form 12 mL spray solution with active ingredients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 49-50.
Table 49. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Flufenacet
Herbicidal Compositions on Weed Control in a Cereal Cropping System.
Figure imgf000109_0001
Compound
A Benzyl Flufenacet Visual Weed Control (%) - 21 DAA
Ester
SASKR STEME
gai/ha gai/ha Obs Exp Obs Exp
2.5 0 15 - 25 -
5 0 50 - 25 -
10 0 67 - 27 -
0 60 5 - 0 -
0 120 5 - 5 -
0 240 13 - 42 -
2.5 60 38 19 75 25
2.5 120 50 19 68 29
5 60 68 53 78 25
5 120 63 53 83 29
5 240 77 57 72 56
10 240 85 71 73 57
Figure imgf000110_0001
Table 50. Synergistic Activity of Foliar- Applied Compound A Benzyl Ester and Prosulfocarb
Herbicidal Compositions on Weed Control in a Cereal Cropping System.
Figure imgf000110_0002
0 1000 15 - 10 - 5 -
0 2000 40 - 15 - 8 -
0 4000 67 - 75 - 27 -
2.5 1000 78 62 65 28 25 22
2.5 2000 78 73 73 32 58 24
5 1000 88 71 75 47 53 17
5 2000 88 80 78 50 55 20
5 4000 93 89 88 85 73 36
10 4000 94 92 92 90 79 36
Compound
A Benzyl Prosulfocarb Visual Weed Control (%) - 21 DAA
Ester
PAPRH SASKR STEME
gai/ha gai/ha Obs Exp Obs Exp Obs Exp
2.5 0 48 - 15 - 25 -
5 0 28 - 50 - 25 -
10 0 35 - 67 - 27 -
0 1000 5 - 5 - 0 -
0 2000 10 - 5 - 10 -
0 4000 13 - 63 - 73 -
2.5 1000 48 50 45 19 50 25
2.5 2000 50 53 65 19 58 33
5 1000 85 32 58 53 55 25
5 2000 60 35 73 53 35 33
5 4000 63 38 80 82 91 80
10 4000 93 44 85 88 81 80
Figure imgf000111_0001
BRSNW Brassica napus L. rape, oilseed (winter)
CHEAL Chenopodium album L. lambsquarters, common
CIRAR Cirsium arvense (L.) Scop. thistle, Canada
GALAP Galium aparine L. cleavers, catchweed bedstraw
KCHSC Kochia scoparia (L.) Schrad. kochia
PAPRH Papaver rhoeas L. poppy, common
SASKR Salsola tragus L. thistle, Russian
SINAR Sinapis arvensis L. mustard, wild
STEME Stellaria media (L.) Vill. chickweed, common
Example IV. Evaluation of Pre-emergence Soil-Applied Herbicidal Mixtures for Weed
Control
Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam soil (32 percent silt, 23 percent clay, and 45 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and calcareous grit in an 80 to
20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm2).
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (compound A) formulated as an SC
(suspension concentrate) and various herbicidal components alone and in combination.
Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:
Figure imgf000112_0001
Compound A Benzyl Ester Other herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid synthesis- inhibiting herbicides alachlor (technical grade material), dimethenamid-P formulated as Outlook®, and S-metolachlor formulated as Dual® II Magnum.
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL application volume at a rate of 187 L/ha.
For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25% (v/v) Agri-Dex® crop oil concentrate (COC) to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) COC so that the final spray solutions contained 1.25% (v/v) COC.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) COC so that the final spray solutions contain 1.25% (v/v) COC. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials were placed individually in 25 mL glass vials and dissolved in a volume of 97:3 (v/v) acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) COC or water to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) COC so that the final spray solutions contained 1.25% (v/v) COC. As required, additional water and/or 97:3 (v/v) acetone/DMSO was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the soil with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 inches (46 cm) above average pot height. Control pots were sprayed in the same manner with the solvent blank.
The treated and control pots were placed in a greenhouse and top watered as needed. When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The pots were maintained in a greenhouse with an approximate 14 hr photoperiod which was maintained at about 29° C during the day and 26° C during the night. Nutrients (Peters® Excel 15-5-15 5-Ca 2-Mg) were applied in the irrigation solution as needed and water was added on a regular basis. Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. After
approximately 4 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 51-54.
Table 51. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Alachlor Herbicidal Compositions on Weed Control
Figure imgf000115_0001
Table 52. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Dimethenamid-P Herbicidal Compositions on Weed Control
Figure imgf000115_0002
Table 53. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and S-Metolachlor Herbicidal Compositions on Weed Control
Figure imgf000115_0003
32 775 38 23
16 1550 65 41
32 1550 53 48
Table 54. Synergistic Activity of Soil-applied, Pre-emergence Applications of Compound A Benzyl Ester and Pethoxamid Herbicidal Compositions on Weed Control
Figure imgf000116_0001
IPOHE Ipomoea hederacea (L.) Jacq. morningglory, ivyleaf
XANST Xanthium strumarium L. cocklebur, common
gae/ha = grams acid equivalent per hectare
gai/ha = grams active ingredient per hectare
Obs = observed value
Exp = expected value as calculated by Colby's equation
DAA = days after application
Example V. Evaluation of Herbicidal Activity of Mixtures Applied Under Field Conditions to Transplanted Rice
Post and pre-emergence field trials were conducted in Niigata, Japan. Trial sites were located in commercially grown fields of transplanted rice (Oryza sativa, variety: Koshihikari) using standard herbicide small plot research methodology. The trial plot size was 2 meters (m) x 2 m with 3 replications. The nursery plants were grown in the greenhouse using practical methods and transplanted into the field at the 2.5-leaf stage on May 07, 2012. The row and in-row spaces were 30 cm and 17 cm, respectively. The crop was grown using normal cultural practices for fertilization, water management and maintenance to ensure good growth of the crop and the weeds.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2- fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid (Compound A) formulated as an SC (suspension concentrate) and various herbicidal components alone and in combination.
Compound A benzyl ester was applied on an active ingredient basis. The herbicidal components were applied on an active ingredient basis and included very long chain fatty acid (VLCFA) synthesis-inhibiting and fatty acid/lipid biosynthesis herbicides pretilachlor formulated as a commercially available granular formulation and benfuresate formulated as a commercially available flowable formulation.
Compound A benzyl ester SC was once diluted in 100 mL water in the 200 mL bottle/plot to achieve the desired rates and applied by water injection. Water injection applications were made by hand as evenly as possible. Pretilachlor was applied by hand, and benfuresate was applied using a pipette to achieve the desired rates. Each compound in mixture treatments was applied separately and successively. Water depth was 3 cm at application. Treatments were rated at 25 and 40 days after application (DAA) for post and pre-emergence trials respectively as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
All treatment results, both for the single product and mixtures, are an average of 3 replicates. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, common barnyardgrass (Echinochloa crus-galli, ECHCG), monochoria (Monochoria vaginalis, MOOVA), Japanese bulrush (Scirpus juncoides,SCPKS), kuroguwai (Eieocharis kuroguwai, ELOKU), common falsepimpernel (Lindernia pyxidaria, LIDPY), Souchet tardif (Cyperus serotinus, CYPSE), small-flower flatsedge (Cyperus difformis, CYPDI), American waterwort (Elatine triandra, ELTTR), and swamp smartweed (Polygonum hydropiperoides, POLHP).
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) . The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100)
A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results for submerged (weeds have not yet emerged from the flood water) weed control are given in Table 55.
Some of the compounds tested, application rates employed, plant species tested, and results for early postemergence weed control are given in Tables 56-57. Table 55. Synergistic Activity of In- Water Applied Compound A Benzyl Ester and
Benfuresate Herbicidal Compositions on Submerged Weed Control in a Transplanted Rice
Cropping System when Evaluated 31 DAA (Days After Application) in Japan.
Figure imgf000118_0001
Table 56. Synergistic Activity of In- Water Applied Compound A Benzyl Ester and
Benfuresate Herbicidal Compositions on Early Post-emergence Weed Control in a
Transplanted Rice Cropping System when Evaluated 11-16 DAA (Days After Application) Japan.
Figure imgf000118_0002
100 0 3.3 - 20.0 -
0 600 6.7 - 20.0 -
100 600 82.3 9.8 89.3 36.0
Table 57. Synergistic Activity of In- Water Applied Compound A Benzyl Ester and Pretilachlor Herbicidal Compositions on Early Post-emergence Weed Control in a Transplanted Rice Cropping System when Evaluated 11 DAA (Days After Application) Japan.
Figure imgf000119_0001
gai/ha = grams active ingredient per hectare
Obs = observed value
Exp = expected value as calculated by Colby's equation
DAA = days after application
ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass
POLHP Polygonum hydropiperoides Michx. smartweed, swamp SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese

Claims

WHAT IS CLAIMED IS:
1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000120_0001
or an agriculturally acceptable salt or ester thereof and (b) VLCFA and fatty acid/lipid synthesis inhibiting herbicides.
2. The composition of claim 1, wherein (a) is the compound of formula (I), a C1-4 alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).
3. The composition of any of claims 1-2, wherein (b) is at least one compound, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole,
dimethenamid-P, fenoxasulfone, fentrazamide, indanofan, flufenacet, mefenacet, s- metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, and thiobencarb.
4. The composition of any of claims 1-3, further comprising an agriculturally acceptable adjuvant or carrier.
5. The composition of any of claims 1-4, further comprising a herbicide safener.
6. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a compound of the formula (I)
Figure imgf000120_0002
or an agriculturally acceptable salt or ester thereof and (b) a VLCFA and fatty acid/lipid synthesis inhibiting herbicide.
7. The method of claim 6, wherein (a) is the compound of formula (I), a C1-4 alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).
8. The method of any of claims 6-7, wherein (b) is at least one compound, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, selected from the group consisting of: acetochlor, alachlor, anilofos, benfuresate, cafenstrole,
dimethenamid-P, fentrazamide, indanofan, flufenacet, mefenacet, s-metolachlor, molinate, pethoxamid, pretilachlor, prosulfocarb, pyroxasulfone, thenylchlor, and thiobencarb.
9. The method of any of claims 6-8, wherein the undesirable vegetation is controlled in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, industrial vegetation management (IVM) or rights of way (ROW).
10. The method of any of claims 6-9, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.
1 1. The method of any of claims 6-10, wherein the undesirable vegetation is controlled in glyphosate-, 5 -enolpyruvylshikimate-3 -phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-,
sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil- tolerant crops.
12. The method of claim 1 1, wherein the tolerant crop possesses multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.
13. The method of any of claims 6-12, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.
121
PCT/US2013/051302 2012-07-24 2013-07-19 Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxphenyl) pyridine-2-carboxylic acid or a derivative thereof and vlcfa synthesis and fatty acid/lipid synthesis inhibiting herbicides Ceased WO2014018397A1 (en)

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