WO2025016884A1 - Compositions herbicides - Google Patents

Compositions herbicides Download PDF

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Publication number
WO2025016884A1
WO2025016884A1 PCT/EP2024/069739 EP2024069739W WO2025016884A1 WO 2025016884 A1 WO2025016884 A1 WO 2025016884A1 EP 2024069739 W EP2024069739 W EP 2024069739W WO 2025016884 A1 WO2025016884 A1 WO 2025016884A1
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WIPO (PCT)
Prior art keywords
component
composition according
herbicidal composition
methyl
weeds
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PCT/EP2024/069739
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English (en)
Inventor
Julia FELLMANN
Melanie Jayne Watkins
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Syngenta Crop Protection AG Switzerland
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Syngenta Crop Protection AG Switzerland
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Priority to AU2024293377A priority Critical patent/AU2024293377A1/en
Priority to CN202480044191.3A priority patent/CN121443146A/zh
Publication of WO2025016884A1 publication Critical patent/WO2025016884A1/fr
Anticipated expiration legal-status Critical
Pending legal-status Critical Current

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Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N41/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10Sulfones; Sulfoxides
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/26Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01PBIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00Herbicides; Algicides

Definitions

  • the present invention relates to novel herbicidal compositions comprising a combination of herbicidal active ingredients which provides control of weeds in crops of useful plants.
  • the invention further provides methods of controlling weeds in crops of useful plants, and to the use of the herbicidal composition to control weeds.
  • fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of Formula (I), and component (B) is mesotrione, or agrochemically acceptable salts, N-oxides, diastereoisomers, enantiomers or tautomers thereof.
  • WO 2016/095768 and WO 2020/063613 disclose herbicide compounds of Formula (I) and processes for making them.
  • EP186118B1 describes mesotrione and processes for making it.
  • WO 2020/234422 and WO 2022/095908 disclose herbicidal mixtures of compounds of Formula (I) and mesotrione.
  • Compounds of Formula (I) are known from WO2016/095768 and W02020/063613 and provide effective control of problematic weeds in crops.
  • Combinations of herbicidal active ingredients are often used in agriculture to increase and/or broaden the control of problematic plants (weeds) in crops of useful plants.
  • the combination can give rise to a valuable greater-than-additive (synergistic) effect which can, for example, enable efficient weed control through lower application rates.
  • the present invention is based upon novel compositions comprising compounds of Formula (I).
  • a herbicidal composition comprising as component (A) a herbicidally effective amount of a compound of Formula (I) wherein R 1 is hydrogen, chloro, or fluoro;
  • R 2 is chloro or bromo
  • R 3 is CO2R 5 or CH2OR 6 ;
  • R 4 is hydrogen, methyl, or ethyl
  • R 5 is hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, allyl, propargyl, Ci-CsalkoxyCi-Csalkyl, C1-
  • R 6 is Ci-C4alkylcarbonyl, cyclopropylcarbonyl, or Ci-C2alkylsulfonyl; and component (B) is mesotrione, or agrochemically acceptable salts, N-oxides, diastereoisomers, enantiomers or tautomers thereof.
  • a method of controlling weeds at a locus comprising applying to the locus of a weed controlling amount of a composition of the present invention.
  • a method of selectively controlling weeds at a locus comprising crop plants and weeds, said method comprising applying to the locus a weed controlling amount of a composition according to the invention.
  • the crop plant is oil palm, corn, cereals, or soy.
  • the crop plant is corn, cereals, or soy.
  • weeds could include, for example, volunteer maize (corn), including genetically-modified maize.
  • C1-C4alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to four carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Examples of C1- C alkyl include, but are not limited to, methyl, ethyl, n-propyl, n-butyl, and the isomers thereof, for example, iso-propyl, iso-butyl, sec-butyl, or tert-butyl.
  • Ci-C4haloalkyl refers to a Ci-C4alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms.
  • Examples of Ci-C4haloalkyl include, but are not limited to difluoromethyl, trifluoromethyl, 1 , 1 -difluoroethyl, and 2,2,2-trifluoroethyl.
  • Ci-Csalkoxy refers to a radical of the formula -OR a where R a is a C1- Csalkyl radical as generally defined above.
  • the term “Ci-C2alkoxy” is to be construed accordingly. Examples of Ci-Csalkoxy include, but are not limited to, methoxy, ethoxy, 1 -methylethoxy (iso-propoxy), and propoxy.
  • Ci-CsalkoxyCi-Csalkyl refers to a radical of the formula RbOR a - wherein Rb is a Ci-Csalkyl radical as generally defined above, and R a is a Ci-Csalkylene radical as generally defined above.
  • Rb is a Ci-Csalkyl radical as generally defined above
  • R a is a Ci-Csalkylene radical as generally defined above.
  • Ci-C2alkoxyCi-C2alkyl is to be construed accordingly. Examples of C1- CsalkoxyCi-Csalkyl, include, but are not limited to, ethoxymethyl, ethoxyethyl, methoxyethyl, and methoxymethyl.
  • Ci-C4alkylcarbonyl refers to a radical of the formula R a C(O)-, wherein Ra is a Ci-C4alkyl radical as generally defined above.
  • Examples of Ci-C4alkylcarbonyl include, but are not limited to, acetyl.
  • Ci-CsalkoxycarbonylCi-Csalkyl refers to a radical of the formula RbOC(O)R a -, wherein Rb is a Ci-Csalkyl radical as generally defined above, and R a is a Ci-Csalkylene radical as generally defined above.
  • Examples of Ci-CsalkoxycarbonylCi-Csalkyl include, but are not limited to, methoxycarbonylmethyl.
  • Ci-C2alkylsulfonyl refers to a radical of the formula -S(O)2Ra wherein R a is a Ci-C2alkyl radical as generally defined above.
  • Examples of Ci-C2alkylsulfonyl include, but are not limited to methylsulfonyl.
  • R 1 is hydrogen, chloro, or fluoro. Preferably, R 1 is chloro or fluoro. More preferabyl, R 1 is fluoro.
  • R 2 is chloro or bromo. Preferably, R 2 is chloro.
  • R 3 is CO2R 5 or CH2OR 6 .
  • R 3 is CO2R 5 .
  • R 4 is hydrogen, methyl, or ethyl. Preferably, R 4 is methyl or ethyl. More preferably, R 4 is methyl.
  • R 5 is hydrogen, Ci-C4alkyl, Ci-C4haloalkyl, allyl, propargyl, Ci-CsalkoxyCi-Csalkyl, C1- CsalkoxycarbonylCi-Csalkyl, or tetrahydrofuranylmethyl.
  • R 5 is Ci-C4alkyl. More preferably, R 5 is ethyl.
  • R 6 is Ci-C4alkylcarbonyl, cyclopropylcarbonyl, or Ci-C2alkylsulfonyl.
  • component (A) is a compound of formula (I), wherein
  • R 1 is fluoro
  • R 2 is chloro
  • R 3 is CO2R 5 ;
  • R 4 is Ci-C4alkyl
  • R 5 is Ci-C4alkyl.
  • component (A) is a compound of formula (la) i.e., a compound of formula (I) wherein
  • R 1 is fluoro
  • R 2 is chloro
  • R 3 is CO2R 5 ;
  • R 4 is methyl
  • R 5 is ethyl
  • Component (A) a compound of formula (la) is referred to as ‘Compound 6’ in WO 2016/095768, and can be prepared according to Example 1 of WO 2016/095768.
  • the weight ratio of component (A) to component (B) in the compositions of the invention is from 1000:1 to 1 :1000, especially from 100:1 to 1 :100, more especially in a ratio from 50:1 to 1 :50, even more especially in a ratio of from 40:1 to 1 :40, even more especially still from 25:1 to 1 :25, very especially from 10:1 to 1 :10, very especially still from 5:1 and 1 :5, and in particular from 5:2 to 2:5.
  • the mass ratio of any two ingredients in each combination is selected as to give the desired, for example, synergistic action. In general, the mass ratio would vary depending on the specific ingredient and how many ingredients are present in the combination. Generally, the mass ratio between any two ingredients in any combination of the present invention, independently of one another, is from 100:1 to 1 :100, including from 99:1 , 98:2, 97:3, 96:4, 95:5, 94:6, 93:7, 92:8, 91 :9, 90:10, 89:11 , 88:12, 87:13, 86:14, 85:15, 84:16, 83:17, 82:18, 81 :19, 80:20, 79:21 , 78:22, 77:23, 76:24, 75:25, 74:26, 73:27, 72:28,
  • Preferred mass ratios between any two components of present invention are from 75:1 to 1 .75, more preferably, 1 :1 to 1 .50, especially 1 :3 to 1 :50, advantageously 1 :3 to 1 :32, such as 1 :4 to 1 :32, for example 1 :4 to 1 :24 or 1 :8 to 1 :16.
  • the mixing ratios are understood to include, on the one hand, ratios by mass and also, on other hand, molar ratios.
  • the ratios of 1 :8, 1 :6, 1 :4, 1 :1 , and 2:1 are preferred.
  • the weight ratio of component (A) to component (B) is from 20:1 to 1 :20.
  • the weight ratio of component (A) to component (B) is from 10:1 to 1 :10.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :8.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :8, and the weed species controlled is selected from Echinochloa sp. and Lolium sp..
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :6.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :6, and the weed species controlled is selected from Alopecurus sp., Echinochloa sp., Ipomoea sp., Lolium sp., and Setaria sp..
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :8, and the weed species controlled is selected from Echinochloa crus-galli and Lolium perenne.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :6, and the weed species controlled is selected from Alopecurus myosuroides, Echinochloa crus-galli, Ipomoea hederacea, Lolium perenne, and Setaria faberi.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :4, and the weed species controlled is Alopecurus sp..
  • the weight ratio of component (A) to component (B) is 2:1
  • the weed species controlled is Alopecurus sp..
  • the weight ratio of component (A) to component (B) is 2:1
  • the weed species controlled is Alopecurus myosuroides.
  • the weight ratio of component (A) to component (B) is from 2:1 to 1 :4, and the weed species controlled is Alopecurus myosuroides.
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is selected from Alopecurus sp. and Echinochloa sp..
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is selected from Alopecurus myosuroides and Echinochloa crus-galli.
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Alopecurus sp..
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Alopecurus myosuroides.
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Echinochloa sp..
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Echinochloa crus-galli.
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Lolium sp..
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Lolium perenne. In one embodiment, the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Ipomoea sp..
  • the weight ratio of component (A) to component (B) is 1 :4, and the weed species controlled is Ipomoea hederacea.
  • the weight ratio of component (A) to component (B) is 1 :6, and the weed species controlled is selected from Ipomoea sp., Lolium sp., and Setaria sp..
  • the weight ratio of component (A) to component (B) is 1 :6, and the weed species controlled is selected from Ipomoea hederacea, Lolium perenne, and Setaria faberi.
  • the weight ratio of component (A) to component (B) is 1 :8, and the weed species controlled is selected from Echinochloa crus-galli and Lolium perenne.
  • the herbicidal composition further comprises one or more additional herbicidal component(s) (C), thus providing 3-way, 4-way or even 5-way or more mixes.
  • Component (C) can, for example, be an auxin herbicide (e.g. 2,4-D or dicamba including acceptable salts thereof), an HPPD-inhibiting herbicide, an ACCase-inhibiting herbicide (e.g. clethodim) or a VLCFA herbicide, especially those selected from the group consisting of acetochlor, metolachlor and S-metolachlor and pyroxasulfone, preferably S-metolachlor.
  • an auxin herbicide e.g. 2,4-D or dicamba including acceptable salts thereof
  • HPPD-inhibiting herbicide e.g. clethodim
  • ACCase-inhibiting herbicide e.g. clethodim
  • VLCFA herbicide especially those selected from the group consisting of acetochlor, metolachlor and S-metolachlor and pyroxasulfone, preferably S-metolachlor.
  • component (C) is a herbicide selected from bicyclopyrone, paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxazin, tiafenacil, pyroxasulfone S-metolachlor, glufosinate, L- glufosinate, glyphosate, metribuzin, and [3-(2-methoxy-4-prop-1-ynyl-phenyl)-4-oxo-2-bicyclo[3.2.1]oct- 2-enyl] methyl carbonate.
  • a herbicide selected from bicyclopyrone, paraquat dibromide, diquat dibromide, saflufenacil, trifludimoxazin, tiafenacil, pyroxasulfone S-metolachlor, glufosinate, L- glufosinate, glyphosate, metribuzin,
  • component (A) When applied in a composition of the invention component (A) is typically applied at a rate of 25 to 2000 g ha, more particularly 25, 50, 75, 100, 125, 150, 200, 250, 300, 400, 500, 750, 800, 1000, 1250, 1500, 1800, or 2000 g/ha.
  • Such rates of component (A) are applied typically in association with 5 to 2000g/ha of component (B), and more specifically in association with 5, 10, 15, 20, 25, 50, 75, 100, 120, 125, 140, 150, 200, 240, 250, 300, 400, 480, 500, 750, 1000, 1250, 1500, 1800, or 2000g/ha of component (B).
  • the Examples described herein illustrate but do not limit the range of rates of components (A) and (B) that may be employed in the invention.
  • the amount of a composition according to the invention to be applied will depend on various factors, such as the compounds employed; the subject of the treatment, such as, for example plants, soil or seeds, the type of treatment, such as, for example spraying, dusting or seed dressing, or the application time.
  • the application rates of the composition according to the invention depend on the type of effect desired, and typically range from 30 to 4000 g of total composition per hectare, and more commonly between 30 and 2000g/ha.
  • the application is generally made by spraying the composition, typically by tractor mounted sprayer for large areas, but other methods such as dusting (for powders), drip or drench can also be used.
  • the herbicidal composition further comprises a herbicide safener.
  • a herbicide safener selected from benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole, isoxadifen, mefenpyr, metcamifen and oxabetrinil.
  • the weeds comprise species selected from Abutilon sp., Alopecurus sp., Amaranthus sp., Brachiaria sp., Borreria sp., Chenopodium sp., Commelina sp., Digitaria sp., Echinochloa sp., Eleusine sp., Erigeron sp., Ipomoea sp., Kochia sp., Lolium sp., Portulaca sp., Setaria sp., Sorghum sp., and Stellaria sp..
  • compositions according to the invention over crops that are resistant to the compound of formula (I).
  • Crops may have been rendered resistant to the compound of formula (I) by conventional methods of breeding or by genetic engineering.
  • a composition according to the invention to control weeds that are resistant to other PPO herbicides except the compound of formula (I), such as flumioxazin, fomesafen, and/or lactofen.
  • the weeds may have been rendered tolerant to PPO herbicides by evolution, by conventional methods of breeding or by genetic engineering. Examples include Amaranthus palmeri and Amaranthus tuberculatus that has evolved resistance to PPO herbicides.
  • a method for controlling the growth of protoporphyrinogen IX oxidase (PPO) inhibitor herbicide resistant weeds which comprises applying to the weed, part of the weed, weed propagation material, or the locus of the weed, an effective amount of a composition according to the invention, wherein the PPO-resistant weeds are weeds that are resistant to at least one PPO-inhibiting herbicide, except the compounds of Formula (I).
  • PPO protoporphyrinogen IX oxidase
  • a method for controlling the growth of PPO-resistant weeds which comprises applying to the weed, part of the weed, weed propagation material, or the locus of the weed, an effective amount of a composition according to the invention, wherein the PPO-resistant weeds are weeds that are resistant to at least one PPO-inhibiting herbicide, except the compounds of Formula (I), and have a mutation at amino acid 98, amino acid 210, amino acid 361 , and/or amino acid 399 in the gene coding for the protoporphyrinogen oxidase enzyme.
  • a method for controlling the growth of PPO-resistant weeds which comprises applying to the weed, part of the weed, weed propagation material, or the locus of the weed, an effective amount of a composition according to the invention, wherein the PPO-resistant weeds have a mutation at amino acid 98, amino acid 210, and/or amino acid 399 in the gene coding for the protoporphyrinogen oxidase enzyme.
  • compositions according to the invention over the top of crops that are tolerant to PPO inhibitors.
  • PPO protoporphyrinogen oxidase
  • Such plants can be obtained, for example, by transforming crop plants with nucleic acids which encode a suitable protoporphyrinogen oxidase, which may contain a mutation in order to make it more resistant to the PPO inhibitor.
  • nucleic acids and crop plants are disclosed in WO95/34659, WO97/32011 , W02007/024739, W02012/080975, WO2013/189984, WO2015/022636, WO2015/022640, WO2015/092706, WO2016/099153, WO2017/023778, WO2017/039969, WO2017/217793, WO2017/217794, WO2018/114759, WO2019/117578, WO2019/117579 and WO2019/118726.
  • the crop plants which are tolerant to PPO inhibitors comprise a gene encoding for the HemG enzyme H N90, as disclosed in WO2017/023778 and W02024/015950.
  • the crop plants which are tolerant to PPO inhibitors are cotton, corn, and soy.
  • X % action by first active ingredient using p ppm of the active ingredient
  • synergism corresponds to a positive value for the difference of (O-E).
  • expected activity said difference (O-E) is zero.
  • a negative value of said difference (O-E) signals a loss of activity compared to the expected activity.
  • the combination of the present invention takes advantage of any additive herbicidal activity, and certain embodiments may even exhibit a synergistic effect. This occurs whenever the action of an active ingredient combination is greater than the sum of the actions of the individual components.
  • Combinations of the invention may also provide for an extended spectrum of activity in comparison to that obtained by each individual component, and/or permit the use of lower rates of the individual components when used in combination to that when used alone, in order to mediate effective herbicidal activity.
  • composition of the invention may show increased crop tolerance, when compared with the effect of the component (A) alone. This occurs when the action of an active ingredient combination is less damaging to a useful crop than the action of one of the active ingredients alone.
  • composition should be interpreted as meaning the various mixtures or combinations of components (A) and (B), for example in a single “ready -mix” form, in a combined spray mixture composed from separate formulations of the single active ingredient components, such as a tank-mix , and in a combined use of the single active ingredients when applied in a sequential manner, i.e., one after the other with a reasonably short penod, such as a few hours or days.
  • the order of applying the components (A) and (B) is not essential for working the present invention.
  • herbicide as used herein means a compound that controls or modifies the growth of plants.
  • herbicidally effective amount means the quantity of such a compound or combination of such compounds that is capable of producing a controlling or modifying effect on the growth of plants. Controlling or modifying effects include all deviation from natural development, for example killing, retardation, leaf burn, albinism, dwarfing and the like.
  • locus means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits
  • plant propagation material denotes all generative parts of a plant, for example seeds or vegetative parts of plants such as cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants.
  • safener means a chemical that when used in combination with a herbicide reduces the undesirable effects of the herbicide on non-target organisms, for example, a safener protects crops from injury by herbicides but does not prevent the herbicide from killing the weeds.
  • Crops of useful plants in which the composition according to the invention can be used include perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St.
  • perennial and annual crops such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries
  • cereals for example barley, maize (corn), mille
  • Augustine grass and Zoysia grass herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and vines for example grapes.
  • the compositions of the present invention are particularly useful in controlling weeds in oil palm, corn, cereals or soya.
  • Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g, improved storage stability, higher nutritional value and improved flavour). Crops are to be understood as also including those crops which have been rendered tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD-inhibitors) by conventional methods of breeding or by genetic engineering.
  • An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield summer rape (canola).
  • crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant vaneties commercially available under the trade names RoundupReady® and LibertyLink®.
  • Crops are also to be understood as being those which have been rendered resistant to harmful insects by genetic engineering methods, for example Bt maize (resistant to European corn borer), Bt cotton (resistant to cotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).
  • Bt maize are the Bt 176 maize hybrids of NK® (Syngenta Seeds).
  • the Bt toxin is a protein that is formed naturally by Bacillus thuringiensis soil bacteria.
  • Examples of toxins, or transgenic plants able to synthesise such toxins are described in EP-A-451 878, EP-A-374 753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529.
  • transgenic plants comprising one or more genes that code for an insecticidal resistance and express one or more toxins are KnockOut® (maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton), NewLeaf® (potatoes), NatureGard® and Protexcta®.
  • Plant crops or seed material thereof can be both resistant to herbicides and, at the same time, resistant to insect feeding ("stacked" transgenic events).
  • seed can have the ability to express an insecticidal Cry3 protein while at the same time being tolerant to glyphosate.
  • crops that have been rendered tolerant to PPO inhibiting herbicides by genetic engineering are known in the art, for example as described in WO95/34659.
  • crops that have been rendered tolerant to HPPD inhibiting herbicides by genetic engineering are known in the art, for example as described in WO2011/063411 , WO201 1/063413, WO2012/082542, WO2012/082548, WO2010/085705 and WO2011/068567.
  • compositions of the present invention comprising glufosinate and/or glyphosate have potential utility in glyphosate- and glufosinate-resistant crops respectively, especially engineered soybean crops.
  • compositions of the present invention comprising a PPO-inhibiting herbicide have potential utility in PPO-resistant crops, especially engineered soybean crops.
  • the compositions of the present invention especially any comprising 2,4-D (or an agrochemically acceptable ester or salt thereof), have potential utility in crops which are have been engineered to tolerate 2,4-D herbicides, for example EnlistTM crops, especially EnlistE3TM Soybeans.
  • compositions of the present invention especially any comprising dicamba (or an agrochemically acceptable ester or salt thereof) have potential utility in crops which are have been engineered to tolerate dicamba herbicides, for example Roundup Ready 2 XtendTM Soybeans.
  • compositions of the invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species in the crop.
  • the compositions of the present invention provide particular good control of Alopecurus sp. (e.g. Alopecurus myosuroides (ALOMY)), Avena sp. Digitaria sp. (e.g Digitaria sanguinalis (DIGSA), Digitaria insularis (TRCIN)), Echinochloa sp. (e.g Echinochloa crus-galli (ECHCG)), Eleusine sp. (e.g. Eleusine indica (ELEIN)), Lolium sp., Setaria sp. (e.g.
  • Alopecurus sp. e.g. Alopecurus myosuroides (ALOMY)
  • Avena sp. Digitaria sp. e.g Digitaria sanguinalis (DIGSA), Digitaria
  • the weeds may be monocotyledonous or dicotyledonous weeds, which are tolerant or resistant to one or more herbicides for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine or EPSPS inhibitors such as glyphosate.
  • herbicides for example, HPPD inhibitor herbicides such as mesotrione, PSII inhibitor herbicides such as atrazine or EPSPS inhibitors such as glyphosate.
  • Such weeds include, but are not limited to resistant Amaranthus biotypes.
  • compositions of the invention can further include one or more safeners.
  • safeners are especially preferred: benoxacor, cloquintocet (including cloquintocet-mexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlorazole-ethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifen-ethyl), mefenpyr (including mefenpyr-diethyl), metcamifen and oxabetrinil.
  • compositions of the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application), or after weeds emerge (post-emergence application).
  • a safener is combined with mixtures of the invention, it is preferred that the mixing ratio of compound of Formula (I) to safener is from 100:1 to 1 :10, especially from 20:1 to 1 :1 .
  • the safener and the compositions of the invention are applied simultaneously.
  • the safener and the composition of the invention might be applied to the locus preemergence or might be applied to the crop post-emergence.
  • the safener and the composition of the invention are applied sequentially.
  • the safener might be applied before sowing the seeds as a seed treatment and the composition of the invention might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
  • compositions of the invention can be applied before or after planting of the crops, before weeds emerge (pre-emergence application), or after weeds emerge (post-emergence application).
  • a safener is combined with mixtures of the invention, it is preferred that the mixing ratio of component (A) to safener is from 100:1 to 1 :10, preferably from 20:1 to 1 :1 .
  • the safener and the compositions of the invention are applied simultaneously.
  • the safener and the composition of the invention might be applied to the locus preemergence or might be applied to the crop post-emergence.
  • the safener and the composition of the invention are applied sequentially.
  • the safener might be applied before sowing the seeds as a seed treatment and the composition of the invention might be applied to the locus pre-emergence or might be applied to the crop post-emergence.
  • compositions of the invention can advantageously be used in the below-mentioned formulations (in which case "active ingredient” relates to the respective mixture of component (A) with component (B) or, when a safener is also used, the respective mixture of the component (A) with component (B) and the safener).
  • compositions of this invention can also be mixed with one or more further pesticides including herbicides [typically different to the herbicides (A) and (B)], fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection.
  • herbicides typically different to the herbicides (A) and (B)
  • fungicides typically different to the herbicides (A) and (B)
  • insecticides typically different to the herbicides (A) and (B)
  • fungicides typically different to the herbicides (A) and (B)
  • insecticides typically different to the herbicides (A) and (B)
  • fungicides typically different to the herbicides (A) and (B)
  • insecticides typically different to the herbicides (
  • compositions of present invention can also be used in mixture with one or more additional herbicides and/or plant growth regulators.
  • additional herbicides or plant growth regulators include acetochlor, acifluorfen (including acifluorfen-sodium), aclonifen, ametryn, amicarbazone, aminopyralid, aminotriazole, atrazine, beflubutamid-M, benquitrione, bensulfuron (including bensulfuron-methyl), bentazone, bicyclopyrone, bilanafos, bipyrazone, bispyribac-sodium, bixlozone, broclozone, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone-ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron- ethyl), chlorotoluron, chlorsulfuron,
  • compositions according to the invention may be utilised as the technical active ingredient as produced. More typically however, the compositions according to the invention may be formulated in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances.
  • formulation adjuvants such as carriers, solvents and surface-active substances.
  • the formulations can be in various physical forms, e.g.
  • Such formulations can either be used directly or diluted prior to use.
  • the dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.
  • the formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions.
  • the active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.
  • the active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns.
  • Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.
  • a large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use.
  • Surfaceactive substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes.
  • Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate; alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate; soaps, such as sodium stearate; salts of alkylnaphthalenesulfonates, 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 lauryltrimethylammonium chloride, polyethylene glycol esters of
  • Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micronutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.
  • the formulations according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives.
  • the amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied.
  • the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared.
  • Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow.
  • the formulations generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds (A) and (B) and from 1 to 99.9 % by weight of a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • a formulation adjuvant which preferably includes from 0 to 25 % by weight of a surface-active substance.
  • compositions may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • Dusts active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Wettable powders active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 %
  • Granules active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %
  • Wettable powders a) b) c) active ingredients 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % sodium lauryl sulphate 3 % - 5 % sodium diisobutylnaphthalenesulfonate 6 % 10 % phenol polyethylene glycol ether 2 %
  • Powders for dry seed treatment a) b) c) active ingredients 25 % 50 % 75 % light mineral oil 5 % 5 % 5 % highly dispersed silicic acid 5 % 5 %
  • the combination is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredients 10 % octylphenol polyethylene glycol ether 3 %
  • Cyclohexanone 30 % xylene mixture 50 % Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • the combination is mixed and ground with the adjuvants, and the mixture is moistened with water.
  • the mixture is extruded and then dried in a stream of air.
  • the finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol.
  • Non-dusty coated granules are obtained in this manner.
  • Carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredients 40 % propylene glycol 5 % copolymer butanol PO/EO 2 %
  • Silicone oil (in the form of a 75 % emulsion in water) 0.2 %
  • the finely ground combination is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Alopecurus myosuroides Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Lolium perenne (LOLPE), Setaria faberi (SETFA), and Ipomoea hederacea (IPHOE)
  • Alopecurus myosuroides Alopecurus myosuroides (ALOMY), Echinochloa crus-galli (ECHCG), Lolium perenne (LOLPE), Setaria faberi (SETFA), and Ipomoea hederacea (IPHOE)
  • Alopecurus myosuroides Alopecurus myosuroides
  • EHCG Echinochloa crus-galli
  • LPE Lolium perenne
  • SETFA Setaria faberi
  • IPHOE Ipomoea hederacea
  • Test compounds or compositions are applied at the rates stated.
  • Table B1 Post-emergence efficacy for a composition of compound of formula (la) and mesotrione against Alopecurus myosuroides (ALOMY)
  • Table B2 Post-emergence efficacy for a composition of compound of formula (la) and mesotrione against Lolium perenne (LOLPE)
  • Table B3 Post-emergence efficacy for a composition of compound of formula (la) and mesotrione against Setaria faberi (SETFA)
  • Table B4 Post-emergence efficacy for a composition of compound of formula (la) and mesotrione against Ipomoea hederacea (IPHOE)

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  • Wood Science & Technology (AREA)
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Abstract

La présente invention concerne une composition herbicide contenant un mélange de constituants (A) et (B) en tant que principes actifs, le constituant (A) étant un composé de formule (I) et le constituant (B) étant du mésotrione ou un ester ou un sel agrochimiquement acceptable de celui-ci.
PCT/EP2024/069739 2023-07-20 2024-07-11 Compositions herbicides Pending WO2025016884A1 (fr)

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