WO2006061562A1 - Herbicidal composition - Google Patents

Herbicidal composition Download PDF

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Publication number
WO2006061562A1
WO2006061562A1 PCT/GB2005/004468 GB2005004468W WO2006061562A1 WO 2006061562 A1 WO2006061562 A1 WO 2006061562A1 GB 2005004468 W GB2005004468 W GB 2005004468W WO 2006061562 A1 WO2006061562 A1 WO 2006061562A1
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WIPO (PCT)
Prior art keywords
compound
composition according
glyphosate
methyl
vegetation
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PCT/GB2005/004468
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French (fr)
Inventor
Daniel Joseph North
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Syngenta Participations AG
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Syngenta Participations AG
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Priority claimed from GB0426717A external-priority patent/GB0426717D0/en
Priority claimed from GB0503346A external-priority patent/GB0503346D0/en
Priority to AU2005313141A priority Critical patent/AU2005313141A1/en
Application filed by Syngenta Participations AG filed Critical Syngenta Participations AG
Priority to EP05804388A priority patent/EP1824337A1/en
Priority to MX2007006425A priority patent/MX2007006425A/en
Priority to US11/720,614 priority patent/US20090233796A1/en
Priority to JP2007543902A priority patent/JP2008522965A/en
Priority to BRPI0518463-0A priority patent/BRPI0518463A2/en
Priority to CA002586256A priority patent/CA2586256A1/en
Publication of WO2006061562A1 publication Critical patent/WO2006061562A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to a herbicidal composition and to a method of controlling the growth of undesirable vegetation using this composition or a combination of its components.
  • US patent 6 537 948 discloses a broad range of compounds as herbicides. This patent also discloses that these compounds can be used in admixture with a wide range of other agricultural additives, including a long list of other herbicides. We have now discovered that certain selected herbicide mixtures are unexpectedly effective in controlling weeds.
  • the present invention relates to a herbicidal composition
  • a herbicidal composition comprising;
  • R 1 is Cl to C3 alkyl or Cl to C3 haloalkyl
  • R 2 is Cl to C3 alkyl
  • X 1 and X 2 are halogen
  • R 3 is a Cl -6 alkanoic acid C 1-6 alkyl ester residue
  • R 1 is methyl substituted with fluorine, for example trifluoromethyl, chlorodifluoromethyl, difluoromethyl, or ethyl substituted with fluorine, for example, pentafluoroethyl, 1 , 1 -difluoroethyl. Most preferably R 1 is trifluoromethyl.
  • R 2 is methyl or ethyl, more preferably methyl,
  • the C 1-6 alkanoic acid can be for example ethanoic, propionic, pentanoic or hexanoic acid, preferably ethanoic acid
  • the C 1-6 alkyl ester is derived from, for example, ethanol, propanol , isopropanol, butanol, isobutanol, tertiary butanol, pentanol, isopentanol, hexanol or isohexanol, preferably methanol or ethanol, more preferably ethanol.
  • R 3 is -CH 2 COOCH 3 or -CH 2 COOCH 2 CH 3 , and particularly preferred is -CH 2 COOCH 2 CH 3 .
  • X 1 and X are preferably independently chlorine or fluorine. Most preferably X 1 is fluorine. Most preferably X 2 is chlorine.
  • the most preferred compound (a) is of Formula
  • the herbicides (B) are independently known in the art for their effects on plant growth. Many are disclosed in The Pesticides Manual, Thirteenth Edition, 2003, published by The British Crop Protection Council. Numbers in brackets after herbicide names in this application refer to entries in The Pesticides Manual. Many are also commercially available.
  • Glyphosate (B2) is described as entry 419, page 513 of The Pesticides Manual.
  • glyphosate is used in the form of a salt, such as an ammonia or organic amine salt or such as an alkali metal salt.
  • a salt such as an ammonia or organic amine salt or such as an alkali metal salt.
  • organic amine salts are salts with ethonolamine, isopropylamine or dimethylethanolamine.
  • alkali metal salts are sodium, potassium or lithium salts.
  • Preferred salts are with potassium, ammonia, isopropylamine or ethanolamine.
  • Sulfonylureas (B3) are a well-known class of herbicides of the general formula
  • sulfonylureas are amidosulfuron (22), azimsulfuron (43), bensulfuron- methyl (64), chlorimuron-ethyl (135), chlorsulfuron (147), cinosulfuron (154), cyclosulfamuron (189), ethametsulfuron-methyl (306), ethoxysulfuron (314), flazasulfuron (356), flupyrsulfuron-m ethyl-sodium (384), foramsulfuron (402), halosulfuron-m ethyl (426), imazosulfuron (456), iodosulfuron-methyl-sodium (466), mesosulfuron-methyl (514), metsulfuron-methyl (555), nicosulfuron (577), oxasulfuron (603), primisulfuron-methyl (657), prosulfuron (684), pyrazosulfuron
  • Chloroacetamides (B4) are a well-known class of herbicides of the general formula
  • chloroacetamides examples include acetochlor (5), alachlor (14), butachlor (100), dimethachlor (258), dimethanamid (260), metazachlor (524), metolachlor (548), S- metolachlor (549), pethoxamid (627), pretilachlor (656), propachlor (667), propisochlor (677), thenylchlor (789) .
  • a preferred chloroacetamide is metolachlor, particularly its isomer S -metolachlor.
  • Diphenyl ethers are a known class of herbicides including aciflorofen (7), bifenox (75), fluoroglycofen-efhyl (380), fomesafen (401), lactofen (486), oxyfluorfen (610) and aclonifen (8).
  • a preferred difenyl ether is fomesafen.
  • Triazines (B6) are a well-known class of herbicides which includes ametryn (20), atrazine (37), cyanazine (183), dimethametryn (259), prometon (665), prometryn (606), propazine (672), simazine (730), simetryn (732), terbumeton (774), terbuthylazine (775), terbutryn (776) and trietazine (831).
  • Preferred triazines are simazine and atrazine, more preferred is atrazine.
  • N-Phenylphthalimides are a well-known class of herbicides which include cini don- ethyl (152), flumiclorac-pentyl (375) and flumioxazin (376). Preferred is flumioxazim.
  • Glufosinate (B8) is described as entry 406 of The Pesticides Manual.
  • Phenylpyridazines (B9) are a well-known class of herbicides which includes pyridate (702).
  • Triketones (BlO) are a well-known class of herbicides which includes sulcotrione (747) ⁇ and mesotrione (515). Mesotrione is preferred.
  • Isoxazoles (Bl 1) are a well known class of herbicides including isoxaflutole (479).
  • Cyclohexanedione oximes are a well known class of herbicides including alloxydim (18), butroxydim (106), clethodim (155), cycloxydim (190), sethoxydim (726), tepraloxydim (771) and tralkoxydim (811). Clethodim is preferred.
  • Triazolinones (B 13) are a known class of herbicides including amicarbazone (21), azafenidin (S885), carfentrazone-ethyl (212) and sulfentrazone (749). Carfentrazone- ethyl is preferred.
  • Ureas (B 14) are a known class of herbicide including chlorbromuron (S961), chlorotoluron (143), dimefuron (256), diuron (281), fenuron (Sl 162), fluometuron (378), isoproturon (475), isouron (476), linuron (489), methabenzthiazuron (526), metobenzuron (547), metobromuron (S 1287), metoxuron (553), monolinuron (562), neburon (574), siduron (727) and tebuthiuron (765). Diuron is preferred.
  • Dinitroanilines are a known class of herbicides including benfluraline (59), butralin (105), dinitramine (268), ethalfluralin (305), oryzalin (597), pendimethalin (621) and trifluralin (836). Oryzalin and pendimethalin are preferred.
  • Pinoxaden (B 16) is a new broad spectrum cereals herbicide of the formula
  • herbicides that can also be used as component (B) include aminopyralid, beflubutamid (55), benazolin-ethyl, benefin (59), benflubutamid, bentazone (67), benzfendizone, bilanafos (77), bromoxynil (95), butilate (108), clodinafop-propargyl (156), clomazone (159), clopyralid (162), cloransulam (164), cyhalofop-butyl (195), dicamba (228) and its salts, dichlorprop (324), diclofop-methyl (238), diclosulam (241), difenzoquat (248), diflufenican (251), diflufenzopyr (252), dithiopyr (280), fenoxaprop- P-ethyl (339), fentrazamide (348), flamprop-M (355), florasulam (359), fluazo
  • herbicides that can be used as component (B) are acrolein (10), amitrole (25), ammonium sulfamate (26), anilofos (31), asulam (36), benfuresate (61), bensulide (65), benzobicyclon (69), benzofenap 70), bispyribac-sodium (82), borax (86), bromacil (90), bromobutide (93), butafenacil (101), butamifos (102), cafenstrole (110), carbetamide (117), chlorflurenol-methyl (133), chloridazon (134), chloroacetic acid (138), chlorpropham (144), chlorthal-dimethyl (148), cinmethylin (153), clomeprop (160), cumyluron (180), cyanamide (182), cycloate (187), daimuron (213), dalapon (214), dazomet (216), desmedipham (225), dichloben
  • (B) is selected from (Bl) paraquat, (B2) glyphosate, (B3) a sulfonyl urea, (B4) a chloroanilide or (BlO) a triketone, or their herbicidally effective salts.
  • (B) is selected from paraquat, glyphosate, triasulfuron, nicosulfuron, S-metolachlor, sulcotrione or their herbicidally effective salts. More than one component (B) can be used.
  • compositions of the present invention can provide one or more of a number of advantages over the use of the individual components (A) and (B).
  • the rates of application of the individual components can be markedly reduced while maintaining a high level of herbicidal efficacy.
  • the composition can have a considerably broader weed spectrum against which it is effective than does either of the components alone.
  • the composition can have the potential to control weed species at a low application rate at which the individual compounds alone are ineffective.
  • the composition can have a speed of action which is faster than that which would have been predicted from the speed of the individual components.
  • the composition contains a herbicidally effective amount of a combination of component (A) and component (B).
  • 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.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
  • compositions of this invention preferably also comprise an agriculturally acceptable carrier therefor.
  • the compositions of the invention can be formulated as granules, as wettable powders, as emulsifiable concentrates, as powders or dusts, as flowables, as solutions, as suspensions or emulsions, or as controlled release forms such as microcapsules. These formulations can contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. The optimum amount for any given compound will depend upon formulation, application equipment, and nature of the plants to be controlled.
  • Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers.
  • the particles contain the active ingredient retained in a solid matrix.
  • Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain about 5% to about 95% of the active ingredient plus a small amount of wetting, dispersing, or emulsifying agent.
  • Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid, and may consist entirely of the active compound with . a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from about 0.5% to about 95% of the concentrate.
  • Granular formulations include both extrudates and relatively coarse particles, and are usually applied without dilution to the area in which suppression of vegetation is desired.
  • Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which can be coated with the active compound.
  • Granular formulations normally contain about 5% to about 25% active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
  • Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids that act as dispersants and carriers.
  • Microcapsules are typically droplets or granules of the active material enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically about 1 to 50 microns in diameter. The enclosed liquid typically constitutes about 50 to 95% of the weight of the capsule, and may include solvent in addition to the active compound.
  • Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores.
  • Granules typically range from 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
  • compositions for herbicidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
  • formulations can include wetting, dispersing or emulsifying agents which can facilitate application, for example spray droplet formation, wetting of plant leaves and uptake by plants.
  • examples are alkyl and alkylaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols; esters and fatty amines.
  • These agents when used, normally comprise from 0.1% to 15% by weight of the formulation.
  • composition of the present invention may contain an antidotally effective amount of an antidote (also known as a 'safener') for component (A) or component (B).
  • an antidote also known as a 'safener'
  • Safeners are known in the art and many are commercially available. Examples of suitable antidotes are benoxacor and cloquintocet mexyl.
  • compositions may contain, in addition to components (A) and (B), insecticides (for example pyrethroids, permethrin, lambda cyhalothrin, cypermethryn, thiamethoxam, carbamates, organophosphates), fungicides (for example strobilurins, such as azoxystrobin, chlorothalonil, trizoles, such as propiconazole), growth regulators (for example mepiquat chloride), bactericides, acaracides or nematicides, in order to broaden the spectrum of activity.
  • insecticides for example pyrethroids, permethrin, lambda cyhalothrin, cypermethryn, thiamethoxam, carbamates, organophosphates
  • fungicides for example strobilurins, such as azoxystrobin, chlorothalonil, trizoles, such as propi
  • the composition can be made as a single package containing the herbicides together with other ingredients of the formulation (diluents, emulsifiers, surfactants, etc.).
  • the composition can be prepared by tank mixing, in which the components (A) and (B) are mixed, together with other ingredients of the formulation, shortly before use at the grower site, for example by mixing the components in a spray tank or holding tank ready for application.
  • the invention also relates to the use of the compositions in a method of controlling the growth of undesirable vegetation (weeds), particularly in crops.
  • compositions of the invention so that the compound (A) is applied at a rate of between 1 and 16Og per hectare, more preferably 1 to lOOg/ha.
  • the preferred amount of compound (B) will vary according to the exact chemical nature of (B) and its herbicidal efficacy.
  • paraquat is applied at between 100 and 1000g/ha, preferably between 300 and ' 1000g/ha.
  • Glyphosate is applied at 100 to 5000g/ha.
  • Sulfonylureas are applied at rates of 5 to 100g/ha, preferably 10 to 50 g/ha.
  • Chloroacetamides are applied at 10 to 3500g/ha, preferably 500 to 3000g/ha.
  • the ratios of the two components vary for the same reasons.
  • the ratio of (A) to (B) when (B) is paraquat is between 1 :1000 and 3:2, preferably between 1 :100 and 1 :10.
  • the ratio of (A) to (B) when (B) is a sulfonylurea is between 1:100 and 30:1, preferably between 1 :10 and 5:1.
  • the ratio of (A) to (B) when (B) is a chloroacetamide is between 1 :1000 and 3:2, preferably between 1 :100 and 1 :1.
  • compositions can be applied to the locus where weed control is desired by a convenient method.
  • locus is intended to include soil, seeds, and seedlings, as well as established vegetation.
  • the composition can be used over a wide range of crops, for example perennial crops such as vines citrus fruit, olives, pomme stone fruit, nuts, oil palms & rubber and annual arable crops such as cotton, sugar beet, corn, rice, soya or wheat.
  • Suitable crops include those which are tolerant to one or more of components (A) or (B), such as glyphosate or gluphosinate.
  • Tolerance means a reduced susceptibility to damage caused by a particular herbicide compared to the conventional crop breeds.
  • the tolerance can be natural tolerance produced by selective breeding or can be artificially introduced by genetic modification of the crop. Tolerance is generally necessaryy when the compositions are applied to arable crops post emergence (after the crop seedlings become visible).
  • Component (A) is a PPO inhibitor, also known as a 'Protox' inhibitor.
  • PPO inhibitor also known as a 'Protox' inhibitor.
  • a description of certain crops tolerant to PPO inhibitors is given in published PCT patent application WO95/34659 and also in application WO97/32011.
  • Crops can be modified or bred so as to be tolerant to component (B), for example, EPSPS inhibitors like glyphosate.
  • component (B) for example, EPSPS inhibitors like glyphosate.
  • Certain tolerant crops are now well-known and many are commercially available.
  • Clearf ⁇ eld® summer rape (Canola) has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding.
  • RoundupReady® corn, cotton, sugarbeet, soya, and canola are examples of crops that have been rendered tolerant to glyphosate by genetic engineering
  • LibertyLink® corn, canola, soya and rice are examples of crops that have been rendered tolerant to gluphosinate by genetic engineering.
  • compositions of the invention can be used over crops that contain a combination ('stack') of two of these herbicide resistance traits, for example both PPO resistance and glyphosate resistance.
  • the crops can alternatively, or in addition, be genetically modified to be resistant to other unrelated things such as insects or fungi, for example insect resistant cotton, or corn which is resistant to corn-borer or rootworm.
  • insects or fungi for example insect resistant cotton, or corn which is resistant to corn-borer or rootworm.
  • Such resistance traits are well-known and crops having such traits are commercially available.
  • composition of the present invention can be applied in a variety of ways known to those skilled in the art, at various concentrations.
  • the composition is useful in controlling the growth of undesirable vegetation by preemergence or postemergence application to the locus where weed control is desired.
  • Dust and liquid compositions can be applied by the use of power-dusters, broom and hand sprayers and spray dusters.
  • the formulations can also be applied from airplanes as a dust or a spray or by rope wick applications.
  • dust and liquid formulations can be distributed in the soil or applied to the soil surface only, by spraying or sprinkling.
  • the formulations can also be applied by addition to irrigation water. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as disking, dragging or mixing operations.
  • Pressurized sprayers wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, may also be used.
  • Components (A) and (B) as defined above can also be used in a method for controlling undesireable vegetation comprising separately applying to the locus of such vegetation herbicides (A) and (B), sequentially in either order, as part of a single weed control regime.
  • the components can be each applied to the locus where weed control is desired within a single season. Preferably they are applied close enough together in time for there to be an interaction between the two components (A) and (B).
  • Such a period can be for example within six weeks or each other, more preferably within two weeks, most preferably within one week.
  • compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the Table. The results in the table under each application are the percentage of the plants that were killed.
  • compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • compositions were formulated as an emulsif ⁇ able concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • DAA days after application
  • compositions were formulated as an emulsifiable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • weeds were treated with S-metolachlor (SMOC) alone at an application rate equivalent to 142Og per hectare, Compound (A) alone at rates equivalent to 2Og per hectare and 2Og per hectare and with mixtures of S-metolachlor and the Compound (A) at rates equivalent to the sum of these.
  • S-metolachlor S-metolachlor
  • Compound (A) alone at rates equivalent to 2Og per hectare and 2Og per hectare and with mixtures of S-metolachlor and the Compound (A) at rates equivalent to the sum of these.
  • the compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.
  • compositions were formulated as an emulsifyable concentrate (EC).
  • the weed plots were evaluated after the number of days after application (DAA) indicated in the table.

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Abstract

A synergistic herbicidal composition comprising; (A) a compound of formula (I), in which R1 is C1 to C3 alkyl or C1 to C3 haloalkyl. R2 is C1 to C3 alkyl, X1 and X2 are halogen and R3 is a C1-6 alkanoic acid 1-6 alkyl ester residue, and: (B) a second herbicide selected from; (B1) paraquat, (B2) glyphosate, (B3) sulfonyurea, (B4) chloroacetamide, (B5) diphenyl ether (B6) triazine (B7) N-phenylphthalimide (B8) glufosinate (B9) phenylpyridazine (B10) triketone (B11) isoxazole (B12) cyclohexanedione oxime (B13) triazolinone (B14) urea (B15) dinitroaniline (B16) pinoxaden or their herbicidally effective salts.

Description

HERBICIBAL COMPOSITION
The present invention relates to a herbicidal composition and to a method of controlling the growth of undesirable vegetation using this composition or a combination of its components.
The protection of crops from weeds and other undesireable vegetation is a constantly recurring problem in agriculture. There are an extensive variety of herbicidal chemicals and chemical formulations known for the control of such weeds. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use.
US patent 6 537 948 discloses a broad range of compounds as herbicides. This patent also discloses that these compounds can be used in admixture with a wide range of other agricultural additives, including a long list of other herbicides. We have now discovered that certain selected herbicide mixtures are unexpectedly effective in controlling weeds.
The present invention relates to a herbicidal composition comprising;
(A) a herbicide of formula (I)
(I)
Figure imgf000002_0001
in which R1 is Cl to C3 alkyl or Cl to C3 haloalkyl, R2 is Cl to C3 alkyl, X1 and X2 are halogen and R3 is a Cl -6 alkanoic acid C 1-6 alkyl ester residue, and:
(B) a second herbicide selected from;
(Bl) paraquat
(B2) glyphosate
(B3) a sulfonylurea
(B4) a chloroacetamide (B5) a diphenyl ether
(B6) a triazine
(B7) a N-phenylphthalimide
(B8) glufosinate
(B9) a phenylpyridazine
(BlO) a triketone
(BI l) an isoxazole
(B 12) a cyclohexanedione oxime
(B 13) a triazolinone
(B 14) a urea
(B 15) a dinitroaniline
(B 16) pinoxaden
or their herbicidally effective salts.
Preferably R1 is methyl substituted with fluorine, for example trifluoromethyl, chlorodifluoromethyl, difluoromethyl, or ethyl substituted with fluorine, for example, pentafluoroethyl, 1 , 1 -difluoroethyl. Most preferably R1 is trifluoromethyl.
Preferably R2 is methyl or ethyl, more preferably methyl,
In R3, the C 1-6 alkanoic acid can be for example ethanoic, propionic, pentanoic or hexanoic acid, preferably ethanoic acid, and the C 1-6 alkyl ester is derived from, for example, ethanol, propanol , isopropanol, butanol, isobutanol, tertiary butanol, pentanol, isopentanol, hexanol or isohexanol, preferably methanol or ethanol, more preferably ethanol. Most preferably R3 is -CH2COOCH3 or -CH2COOCH2CH3 , and particularly preferred is -CH2COOCH2CH3.
X1 and X are preferably independently chlorine or fluorine. Most preferably X1 is fluorine. Most preferably X2 is chlorine. The most preferred compound (a) is of Formula
Figure imgf000004_0001
The herbicides (B) are independently known in the art for their effects on plant growth. Many are disclosed in The Pesticides Manual, Thirteenth Edition, 2003, published by The British Crop Protection Council. Numbers in brackets after herbicide names in this application refer to entries in The Pesticides Manual. Many are also commercially available.
Paraquat (Bl) is disclosed and described as entry 614, page 742 of The Pesticides Manual.
Glyphosate (B2) is described as entry 419, page 513 of The Pesticides Manual.
hi practice, glyphosate is used in the form of a salt, such as an ammonia or organic amine salt or such as an alkali metal salt. Examples of organic amine salts are salts with ethonolamine, isopropylamine or dimethylethanolamine. Examples of alkali metal salts are sodium, potassium or lithium salts. Preferred salts are with potassium, ammonia, isopropylamine or ethanolamine.
Sulfonylureas (B3) are a well-known class of herbicides of the general formula;
Figure imgf000004_0002
Examples of sulfonylureas are amidosulfuron (22), azimsulfuron (43), bensulfuron- methyl (64), chlorimuron-ethyl (135), chlorsulfuron (147), cinosulfuron (154), cyclosulfamuron (189), ethametsulfuron-methyl (306), ethoxysulfuron (314), flazasulfuron (356), flupyrsulfuron-m ethyl-sodium (384), foramsulfuron (402), halosulfuron-m ethyl (426), imazosulfuron (456), iodosulfuron-methyl-sodium (466), mesosulfuron-methyl (514), metsulfuron-methyl (555), nicosulfuron (577), oxasulfuron (603), primisulfuron-methyl (657), prosulfuron (684), pyrazosulfuron-ethyl (694), rimsulfuron (721), sulfometuron-methyl (751), sulfosulfuron (752), thifensulfuron- methyl (795), triasulfuron (817), tribenuron-m ethyl (822), trifloxysulfuron-sodium (833), triflusulfuron-methyl (837) and tritosulfuron (843). Preferred sulfonylureas are nicosulfuron, flazasulfuron, trifloxysulfuron and triasulfuron. All of these are described in The Pesticides Manual.
Chloroacetamides (B4) are a well-known class of herbicides of the general formula;
Figure imgf000005_0001
Examples of chloroacetamides are acetochlor (5), alachlor (14), butachlor (100), dimethachlor (258), dimethanamid (260), metazachlor (524), metolachlor (548), S- metolachlor (549), pethoxamid (627), pretilachlor (656), propachlor (667), propisochlor (677), thenylchlor (789) . A preferred chloroacetamide is metolachlor, particularly its isomer S -metolachlor.
Diphenyl ethers (B5) are a known class of herbicides including aciflorofen (7), bifenox (75), fluoroglycofen-efhyl (380), fomesafen (401), lactofen (486), oxyfluorfen (610) and aclonifen (8). A preferred difenyl ether is fomesafen.
Triazines (B6) are a well-known class of herbicides which includes ametryn (20), atrazine (37), cyanazine (183), dimethametryn (259), prometon (665), prometryn (606), propazine (672), simazine (730), simetryn (732), terbumeton (774), terbuthylazine (775), terbutryn (776) and trietazine (831). Preferred triazines are simazine and atrazine, more preferred is atrazine.
N-Phenylphthalimides (B7) are a well-known class of herbicides which include cini don- ethyl (152), flumiclorac-pentyl (375) and flumioxazin (376). Preferred is flumioxazim.
Glufosinate (B8) is described as entry 406 of The Pesticides Manual.
Phenylpyridazines (B9) are a well-known class of herbicides which includes pyridate (702). Triketones (BlO) are a well-known class of herbicides which includes sulcotrione (747) ■ and mesotrione (515). Mesotrione is preferred.
Isoxazoles (Bl 1) are a well known class of herbicides including isoxaflutole (479).
Cyclohexanedione oximes (B 12) are a well known class of herbicides including alloxydim (18), butroxydim (106), clethodim (155), cycloxydim (190), sethoxydim (726), tepraloxydim (771) and tralkoxydim (811). Clethodim is preferred.
Triazolinones (B 13) are a known class of herbicides including amicarbazone (21), azafenidin (S885), carfentrazone-ethyl (212) and sulfentrazone (749). Carfentrazone- ethyl is preferred.
Ureas (B 14) are a known class of herbicide including chlorbromuron (S961), chlorotoluron (143), dimefuron (256), diuron (281), fenuron (Sl 162), fluometuron (378), isoproturon (475), isouron (476), linuron (489), methabenzthiazuron (526), metobenzuron (547), metobromuron (S 1287), metoxuron (553), monolinuron (562), neburon (574), siduron (727) and tebuthiuron (765). Diuron is preferred.
1 Dinitroanilines (B15) are a known class of herbicides including benfluraline (59), butralin (105), dinitramine (268), ethalfluralin (305), oryzalin (597), pendimethalin (621) and trifluralin (836). Oryzalin and pendimethalin are preferred.
Pinoxaden (B 16) is a new broad spectrum cereals herbicide of the formula;
Figure imgf000006_0001
Other herbicides that can also be used as component (B) include aminopyralid, beflubutamid (55), benazolin-ethyl, benefin (59), benflubutamid, bentazone (67), benzfendizone, bilanafos (77), bromoxynil (95), butilate (108), clodinafop-propargyl (156), clomazone (159), clopyralid (162), cloransulam (164), cyhalofop-butyl (195), dicamba (228) and its salts, dichlorprop (324), diclofop-methyl (238), diclosulam (241), difenzoquat (248), diflufenican (251), diflufenzopyr (252), dithiopyr (280), fenoxaprop- P-ethyl (339), fentrazamide (348), flamprop-M (355), florasulam (359), fluazolate (Sl 165), flucarbazone (364), flufenpyr-ethyl (371 ), flumiclorac (375), flurtamone (392), fluroxypyr 390), fluthiacet (395), fluthiamide (369), imazamethabenz-methyl (450), imazamox (451), imazapyr (453), imazaquin (454), imazethapyr (455), ioxynil (467), isoxaben (477), isoxachlortole, isopropazole, ketospiradox , MCPA (499), MCPB (501), mecoprop (503), mecoprop-P (504), picolinafen (646), procarbazone (679), prodiamine (661),. Prohexadione (664), prosulfocarb (683), pyraflufen-ethyl (691), pyridafol, quinclorac (712), quinmerac (713), triallate (816), 2,4-DB (217), 2,4-D (211) and its salts.
Still further herbicides that can be used as component (B) are acrolein (10), amitrole (25), ammonium sulfamate (26), anilofos (31), asulam (36), benfuresate (61), bensulide (65), benzobicyclon (69), benzofenap 70), bispyribac-sodium (82), borax (86), bromacil (90), bromobutide (93), butafenacil (101), butamifos (102), cafenstrole (110), carbetamide (117), chlorflurenol-methyl (133), chloridazon (134), chloroacetic acid (138), chlorpropham (144), chlorthal-dimethyl (148), cinmethylin (153), clomeprop (160), cumyluron (180), cyanamide (182), cycloate (187), daimuron (213), dalapon (214), dazomet (216), desmedipham (225), dichlobenil (229), dimepiperate (257), dimethenamid-P (260), dimethipin (261), dimethylarsinic acid (264), dinoterb (272), diphenamid (274), diquat dibromide (276), DNOC (282), endothal (295), EPTC (299), esprocarb (303), ethofumesate (311), etobenzanid (318), ferrous sulfate (353), fluazifop- butyl (361), fluazifop-P-butyl (362), flucetosulfuron, fluchloralin (365), flufenacet (369), flumetsulam (374), flupropanate (383), flurenol (387), fluridone (388)? flurochloridone
(389), fosamine (406), haloxyfop (427), haloxyfop-P (428), HC-252 (429), hexazinone (440), imazapic (452), indanofan (462), karbutilate (482), lenacil (487), MCPA-thioethyl
(500), mefenacet (505), mefluidide (507), metam (519), metamifop (520), metamitron (521), methylarsonic acid (536), methyldymron (539), methyl isothiocyanate (543), metosulam (552), metribuzin (554), MK-616 (559), molinate (560), naproanilide (571), napropamide (572), naptalam (573), nonanoic acid (583), norflurazon (584), oleic acid (593) (fatty acids), orbencarb (595), oxadiargyl (599), oxadiazon (600), oxaziclomefone
(604), pebulate (617), pendimethalin (621), penoxsulam (622), pentachlorophenol (623), pentanochlor (624), pentoxazone (625), petrolium oils (628), phenmedipham (629), picloram (645), piperophos (650), profluazol, profoxydim (663), propanil (669), propaquizafop (670), propham (674), propoxycarbazone-sodium (679), propyzamide (681), pyrazolynate (692), pyrazoxyfen (695), pyribenzoxim (697), pyributicarb (698), pyriftalid (704), pyriminobac-methyl (707), pyrithiobac-sodium (709), quinoclamine (714), quizalofop (717), quizalofop-P (718), simetryn (732), sodium chlorate (734), tar oils (758), 2,3,6-TB A (759), TCA-sodium (760), terbacil (772), thiazopyr (793), thiobencarb (797), tiocarbazil (807), triaziflam (819), triclopyr (827), trifluralin (836), and triflusulfuron-methyl (837).
Preferably (B) is selected from (Bl) paraquat, (B2) glyphosate, (B3) a sulfonyl urea, (B4) a chloroanilide or (BlO) a triketone, or their herbicidally effective salts. Most preferably (B) is selected from paraquat, glyphosate, triasulfuron, nicosulfuron, S-metolachlor, sulcotrione or their herbicidally effective salts. More than one component (B) can be used.
The compositions of the present invention can provide one or more of a number of advantages over the use of the individual components (A) and (B). The rates of application of the individual components can be markedly reduced while maintaining a high level of herbicidal efficacy. The composition can have a considerably broader weed spectrum against which it is effective than does either of the components alone. The composition can have the potential to control weed species at a low application rate at which the individual compounds alone are ineffective. The composition can have a speed of action which is faster than that which would have been predicted from the speed of the individual components.
The composition contains a herbicidally effective amount of a combination of component (A) and component (B). The term "herbicide" as used herein means a compound that controls or modifies the growth of plants. The term "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. The term "plants" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
The compositions of this invention preferably also comprise an agriculturally acceptable carrier therefor. The compositions of the invention can be formulated as granules, as wettable powders, as emulsifiable concentrates, as powders or dusts, as flowables, as solutions, as suspensions or emulsions, or as controlled release forms such as microcapsules. These formulations can contain as little as about 0.5% to as much as about 95% or more by weight of active ingredient. The optimum amount for any given compound will depend upon formulation, application equipment, and nature of the plants to be controlled.
Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient retained in a solid matrix. Typical solid matrices include fuller's earth, kaolin clays, silicas and other readily wet organic or inorganic solids. Wettable powders normally contain about 5% to about 95% of the active ingredient plus a small amount of wetting, dispersing, or emulsifying agent.
Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquid, and may consist entirely of the active compound with. a liquid or solid emulsifying agent, or may also contain a liquid carrier, such as xylene, heavy aromatic naphthas, isophorone and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and normally applied as a spray to the area to be treated. The amount of active ingredient may range from about 0.5% to about 95% of the concentrate.
Granular formulations include both extrudates and relatively coarse particles, and are usually applied without dilution to the area in which suppression of vegetation is desired. Typical carriers for granular formulations include sand, fuller's earth, attapulgite clay, bentonite clays, montmorillonite clay, vermiculite, perlite and other organic or inorganic materials which absorb or which can be coated with the active compound. Granular formulations normally contain about 5% to about 25% active ingredients which may include surface-active agents such as heavy aromatic naphthas, kerosene and other petroleum fractions, or vegetable oils; and/or stickers such as dextrins, glue or synthetic resins.
Dusts are free-flowing admixtures of the active ingredient with finely divided solids such as talc, clays, flours and other organic and inorganic solids that act as dispersants and carriers. Microcapsules are typically droplets or granules of the active material enclosed in an inert porous shell which allows escape of the enclosed material to the surroundings at controlled rates. Encapsulated droplets are typically about 1 to 50 microns in diameter. The enclosed liquid typically constitutes about 50 to 95% of the weight of the capsule, and may include solvent in addition to the active compound. Encapsulated granules are generally porous granules with porous membranes sealing the granule pore openings, retaining the active species in liquid form inside the granule pores. Granules typically range from 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters in diameter. Granules are formed by extrusion, agglomeration or prilling, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xanthates.
Other useful formulations for herbicidal applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene and other organic solvents.
These formulations can include wetting, dispersing or emulsifying agents which can facilitate application, for example spray droplet formation, wetting of plant leaves and uptake by plants. Examples are alkyl and alkylaryl sulfonates and sulfates and their salts; polyhydric alcohols; polyethoxylated alcohols; esters and fatty amines. These agents, when used, normally comprise from 0.1% to 15% by weight of the formulation.
If necessary or desired for a particular application or crop, the composition of the present invention may contain an antidotally effective amount of an antidote (also known as a 'safener') for component (A) or component (B). Safeners are known in the art and many are commercially available. Examples of suitable antidotes are benoxacor and cloquintocet mexyl.
Further, other biocidally active ingredients or compositions may be combined with the composition of this invention. For example, the compositions may contain, in addition to components (A) and (B), insecticides (for example pyrethroids, permethrin, lambda cyhalothrin, cypermethryn, thiamethoxam, carbamates, organophosphates), fungicides (for example strobilurins, such as azoxystrobin, chlorothalonil, trizoles, such as propiconazole), growth regulators (for example mepiquat chloride), bactericides, acaracides or nematicides, in order to broaden the spectrum of activity.
The composition can be made as a single package containing the herbicides together with other ingredients of the formulation (diluents, emulsifiers, surfactants, etc.). Alternatively the composition can be prepared by tank mixing, in which the components (A) and (B) are mixed, together with other ingredients of the formulation, shortly before use at the grower site, for example by mixing the components in a spray tank or holding tank ready for application.
The invention also relates to the use of the compositions in a method of controlling the growth of undesirable vegetation (weeds), particularly in crops.
It is preferred to apply the compositions of the invention so that the compound (A) is applied at a rate of between 1 and 16Og per hectare, more preferably 1 to lOOg/ha. The preferred amount of compound (B) will vary according to the exact chemical nature of (B) and its herbicidal efficacy. For example, paraquat is applied at between 100 and 1000g/ha, preferably between 300 and ' 1000g/ha. Glyphosate is applied at 100 to 5000g/ha. Sulfonylureas are applied at rates of 5 to 100g/ha, preferably 10 to 50 g/ha. Chloroacetamides are applied at 10 to 3500g/ha, preferably 500 to 3000g/ha. The ratios of the two components vary for the same reasons. The ratio of (A) to (B) when (B) is paraquat is between 1 :1000 and 3:2, preferably between 1 :100 and 1 :10. The ratio of (A) to (B) when (B) is glyphosate between 1 :1000 and 3:2, preferably between 1:100 and
1 :10. The ratio of (A) to (B) when (B) is a sulfonylurea is between 1:100 and 30:1, preferably between 1 :10 and 5:1. The ratio of (A) to (B) when (B) is a chloroacetamide is between 1 :1000 and 3:2, preferably between 1 :100 and 1 :1. Once it is appreciated that synergy is obtainable by the present invention, it is a routine matter to determine the appropriate level of each component required to achive the desired level of weed control.
The compositions can be applied to the locus where weed control is desired by a convenient method. The "locus" is intended to include soil, seeds, and seedlings, as well as established vegetation.
The composition can be used over a wide range of crops, for example perennial crops such as vines citrus fruit, olives, pomme stone fruit, nuts, oil palms & rubber and annual arable crops such as cotton, sugar beet, corn, rice, soya or wheat. Suitable crops include those which are tolerant to one or more of components (A) or (B), such as glyphosate or gluphosinate. Tolerance means a reduced susceptibility to damage caused by a particular herbicide compared to the conventional crop breeds. The tolerance can be natural tolerance produced by selective breeding or can be artificially introduced by genetic modification of the crop. Tolerance is generally necesary when the compositions are applied to arable crops post emergence (after the crop seedlings become visible).
Component (A) is a PPO inhibitor, also known as a 'Protox' inhibitor. A description of certain crops tolerant to PPO inhibitors is given in published PCT patent application WO95/34659 and also in application WO97/32011.
Crops can be modified or bred so as to be tolerant to component (B), for example, EPSPS inhibitors like glyphosate. Certain tolerant crops are now well-known and many are commercially available. For example Clearfϊeld® summer rape (Canola) has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding. RoundupReady® corn, cotton, sugarbeet, soya, and canola are examples of crops that have been rendered tolerant to glyphosate by genetic engineering, and LibertyLink® corn, canola, soya and rice are examples of crops that have been rendered tolerant to gluphosinate by genetic engineering.
The compositions of the invention can be used over crops that contain a combination ('stack') of two of these herbicide resistance traits, for example both PPO resistance and glyphosate resistance.
The crops can alternatively, or in addition, be genetically modified to be resistant to other unrelated things such as insects or fungi, for example insect resistant cotton, or corn which is resistant to corn-borer or rootworm. Such resistance traits are well-known and crops having such traits are commercially available.
The composition of the present invention can be applied in a variety of ways known to those skilled in the art, at various concentrations. The composition is useful in controlling the growth of undesirable vegetation by preemergence or postemergence application to the locus where weed control is desired.
These formulations can be applied to the areas where weed control is desired by conventional methods. Dust and liquid compositions, for example, can be applied by the use of power-dusters, broom and hand sprayers and spray dusters. The formulations can also be applied from airplanes as a dust or a spray or by rope wick applications. To modify or control growth of germinating seeds or emerging seedlings, dust and liquid formulations can be distributed in the soil or applied to the soil surface only, by spraying or sprinkling. The formulations can also be applied by addition to irrigation water. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as disking, dragging or mixing operations.
Pressurized sprayers, wherein the active ingredient is dispersed in finely-divided form as a result of vaporization of a low boiling dispersant solvent carrier, may also be used.
Components (A) and (B) as defined above can also be used in a method for controlling undesireable vegetation comprising separately applying to the locus of such vegetation herbicides (A) and (B), sequentially in either order, as part of a single weed control regime. The components can be each applied to the locus where weed control is desired within a single season. Preferably they are applied close enough together in time for there to be an interaction between the two components (A) and (B). Such a period can be for example within six weeks or each other, more preferably within two weeks, most preferably within one week.
The invention is illustrated by the following, non-limiting, examples;
Examples
In the following examples, a compound (A) of Formula (I) was used in which R is -CF3, R2 is Methyl, R3 is -CH2COOCH2CH3, X1 is F, and X2 is Cl (as Formula H) 1. Compound (A) with paraquat
In these tests, various weeds were treated with paraquat alone at rates equivalent to 70Og per hectare and 84Og per hectare, compound (A) alone at rates equivalent to 1Og per hectare and 2Og per hectare, and with a mixture of paraquat and compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the table under each application are the percentage of the weeds plants that were killed. paraquat Compound (A) paraquat + Pyridine cpd
700+ 700+ 840+ 840+
No. Weed Name DAA 700g/ha 840g/ha 10g/ha 20g/ha 10g/ha 20g/ha 10g/ha 20g/ha
1.1 CONYZA SP. 5 2 37 40 55 89
1.2 SETARIA SP. 27 O O 25 O 80
SETARIA
1.3 43 O O 23 O 73 VIRIDIS
LOLIUM
1.4 41 53 27 47 70 87 RIGIDUM
LAMIUM
1.5 2 53 30 33 77 77 PURPUREUM
VERONICA
1.6 69 25 25 100 80 80 PERSICA
DIGITARIA
1.7 51 O O O 68 CILIARIS
ECHINOCHLOA
1.8 51 O O O O 47 CRUS-GALLI
1.9 CONYZA SP. 5 2 37 40 55 89
SONCHUS
1.10 32 O 60 55 83 83 ASPER
CYPERUS
1.11 56 65 O O 88 68 ROTUNDUS
It is very clear from the table that mixtures of compound (A) and paraquat show efficacy far in excess of that expected from the individual components over certain of these weeds. 2. Compound (A) with Glyphosate
In these tests, various weeds were treated with glyphosate alone at a rate equivalent to 84Og per hectare, Compound (A) alone at rates equivalent to 1Og per hectare and 2Og per hectare, and with a mixture of glyphosate and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the table under each application are the percentage of the plants that were killed. glyphosate+
Glyphosate Compound (A) compound (A) 840g/ha 840g/ha
No. Weed Species DAA 840g/ha 10g/ha 20g/ha + 10g/ha +20g/ha
2.1 CYNODON DACTYLON 82 O 0 0 30 30
2.2 DIGITARIA SANGUINALIS 52 O 0 0 43 55
2.3 CYPERUS SP. 1 O 0 0 20 18
2.4 CYPERUS SP. 52 O 0 0 50 70
2.5 CYPERUS ROTUNDUS 2 O 40 75 60 95
2.6 HORDEUM PUSILLUM 13 30 60 70 100 100
It is very clear from the table that mixtures of Compound (A) and glyphosate show efficacy far in excess of that expected from the individual components
3. Compound (A) with Sulfonylureas 3 (a) with triasulfuron
In these tests, various weeds were treated with triasulfuron alone at a rate equivalent to 26g per hectare, Compound (A) alone at a rate equivalent to 1Og per hectare, and to a mixture of triasulfuron and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the Table. The results in the table under each application are the percentage of the plants that were killed.
Compound -,- . ,, Tπasulfuron +
,„ . Triasu furon _ . / Λ \
(A) Compound (A)
No. Weed Species DAA 10 26 10+26
3.1 STELLARIA MEDIA 30 63 25 94
It is very clear from the table that mixtures of the Compound (A) and glyphosate show efficacy far in excess of that expected from the individual components.
3b with nicosulfuron hi these tests, various weeds were treated with nicosulfuron alone at a rate equivalent to 35g per hectare, Compound (A) alone at rates equivalent to 1 Og per hectare, 2Og per hectare, and 3Og per hectare and to mixtures of nicosulfuron and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the table under each application are the percentage of the plants that were killed.
Figure imgf000016_0001
SP.
CYPERUS
3 9 12 0 0 0 30 40 70 75 ESCULENTUS
3.10 IPOMOEA SP. 5 0 30 80 95 95 95 95
3.11 SETARIA VIRIDIS 4 20 40 70 85 75 98
AMARANTHUS
3.12 58 0 50 70 97 80 97 RUDIS
ABUTILON
3.13 27 50 0 98 99 94 95 100 THEOPHRASTI
DIGITARIA
3.14 5 0 25 50 99 90 80 90 SANGUINALIS
AMBROSIA
3.15 28 0 50 50 60 25 60 75 TRIFIDA
BRACHIARIA
3.16 24 35 0 0 0 50 25 PLATYPHYLLA
BRACHIARIA
3.17 30 30 0 0 0 40 30 PLATYPHYLLA
3.18 COMMELINA SP. 10 0 30 50 58 50 98 98
3.19 COMMELINA SP. 17 0 20 30 50 60 99 99
3(c) Mixture with primisulfiiron
In these tests, various weeds were treated with primisulfuron alone at a rate equivalent to 35g per hectare, Compound (A) alone at rates equivalent to 1Og per hectare, 2Og per hectare, and 3Og per hectare and to mixtures of primisulfuron and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifϊable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table. The results in the tables under each application are the percentage of the plants that were killed.
Primisulfuron (g/ha) Compound (A) (g/ha)
Weed
Trial No DAA 30 15 7.5 5 2.5 1.25 Species
3.20 Euphorbia 45 50 30 10 70 70 50
3.21 lpomoea 44 25 20 0 100 100 80
Primisulfuron + Compound (A) (g/ha)
Weed 30+
Trial No DAA 15+ 57.5+ 5 30+ 15+ 7.5+ 30+ 15+ 7.5+ Species 5 2.5 2.5 2.5 1.25 1.25 1.25
3.22 Euphorbia 45 98 98 98 90 80 80 90 80 80
3.23 lpomoea 44 100 100 100 100 100 100 100 90 90 3(d) Mixture with prosulfuron
In these tests, various weeds were treated with prosulfuron alone at a rate equivalent to 35g per hectare, Compound (A) alone at rates equivalent to 1Og per hectare, 2Og per hectare, and 3Og per hectare and to mixtures of prosulfuron and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifiable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the tables under each application are the percentage of the plants that were killed.
Prosulfuron (g/ha) Compound (A) (g/ha)
Weed
No. DAA 30 15 7.5 5 2.5 1.25 Species
3.24 Galium 13 70 40 30 100 50 50
3.25 Veronica 13 15 0 0 100 100 80
3.26 Corn 13 0 0 0 98 90 70
3.27 Brachiaria 13 0 0 0 98 60 50
3.28 Euphorbia 13 30 20 20 70 70 50
3.29 Rice 13 0 0 0 90 70 50
3.30 Wheat 13 0 0 0 100 95 80
Prosulfuron + Compound (A) (g/ha)
Weed 30+ „ -. ς 30+ 30+ 15+
No. DAA 15+ 57.5+ 5 2 5 15+ 7.5+ 7.5+ Species 5 2.5 2.5 1.25 1.25 1.25
3.31 Galium 13 90 90 80 70 70 70 50 50 50
3.32 Veronica 13 100 100 100 100 100 100 100 100 100
3.33 Corn 13 100 100 95 98 95 90 80 60 60
3.34 Brachiaria 13 100 100 100 90 90 50 90 90 40
3.35 Euphorbia 13 98 98 90 100 90 90 100 100 100
3.36 Rice 13 95 95 95 60 60 60 60 50 40
3.37 Wheat 13 100 100 100 100 100 100 90 100 100
4. Mixture with S-metolachlor
In these tests, various weeds were treated with S-metolachlor (SMOC) alone at an application rate equivalent to 142Og per hectare, Compound (A) alone at rates equivalent to 2Og per hectare and 2Og per hectare and with mixtures of S-metolachlor and the Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC). The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the table under each application are the percentage of the plants that were killed.
Compound (A) SMOC SMOC+Compound (A)
1420+ 1420+
Trial No Weed Name DAA 20g/ha 40g/ha 1420g/ha 20g/ha 40g/ha
ECHINOCHLOA
4.1 CRUS-GALLI 28 53 55 75 93 73
SESBANIA
4.2 EXALTATA 56 50 25 20 73 . 83
ABUTILON
4.3 THEOPHRASTI 23 43 78 13 80 93
ABUTILON
4.4 THEOPHRASTI 38 35 70 O 60 80
CHENOPODIUM
4.5 ALBUM 26 80 80 O 92 97
CHENOPODIUM
4.6 ALBUM 54 O 44 O 85 74
AMBROSIA
4.7 ARTEMISIIFOLIA 25 47 79 30 86 97
AMBROSIA
4.8 ARTEMISIIFOLIA 49 30 69 . , 30 78 85
4.9 IPOMOEA SP. 25 35 65 O 65 87
4.10 IPOMOEA SP. 49 20 60 O 65 79
CHENOPODIUM
4.11 ALBUM 56 O 13 O 18 23
ABUTILON
4.12 THEOPHRASTI 15 25 88 65 80 97
ABUTILON
4.13 THEOPHRASTI 56 O 13 O 13 0
POLYGONUM
4.14 PENSYLVANICUM 56 O 13 O O 30
AMBROSIA
4.15 TRIFIDA 42 23 38 25 80 85
AMBROSIA
4.16 TRIFIDA 8 75 95 25 95 97
XANTHIUM
4.17 STRUMARIUM 26 25 73 38 90 95
XANTHIUM
4.18 STRUMARIUM 42 23 68 30 63 ' 65
It is very clear from the table that mixtures of Compound (A) and S-metolachlor show efficacy far in excess of that expected from the individual components over certain of these weeds 5. Mixture with sulcotrione
In these tests, various weeds were treated with sulcotrione alone at an application rate equivalent to 142Og per hectare, Compound (A) alone at rates equivalent to 2Og per hectare and 2Og per hectare and with mixtures of S-metolachlor and Compound (A) at rates equivalent to the sum of these. The compositions were formulated as an emulsifyable concentrate (EC).
The weed plots were evaluated after the number of days after application (DAA) indicated in the table.
The results in the table under each application are the percentage of the plants that were killed.
Sulcotrione
Compound (g/ha)
(A) (g/ha) Compound (A) + sulcotrione (g/ha)
Trial Weed 1.25+ 1.25+ 1.25+ 5+ 5+ 5+
No Name DAA 1.25 5 200100 50 200 100 50 200 100 50
5.1 Cyperus 14 50 50 30 30 25 90 50 50 90 80 70

Claims

WHAT IS CLAIMED IS:
1. A herbicidal composition comprising;
(A) a herbicide of formula (I)
Figure imgf000021_0001
in which R1 is Cl to C3 alkyl or Cl to C3 haloalkyl. R2 is Cl to C3 alkyl, X1 and X2 are halogen and R3 is a C 1-6 alkanoic acid C 1-6 alkyl ester residue, and:
(B) a second herbicide selected from;
(Bl) paraquat
(B2) glyphosate
(B3) a sulfonylurea
(B4) a chloroacetamide
(B5) a diphenyl ether
(B 6) a triazine
(B7) a N-phenylphthalimide
(B8) glufosinate
(B9) a phenylpyridazine
(BlO) a triketone
(BI l) an isoxazole
(B12) a cyclohexanedione oxime (B 13) a triazohnone
(B 14) a urea
(B 15) a dinitroaniline
(B 16) a pinoxaden
or their herbicidally effective salts.
2. A composition according to claim 1, wherein component (B) is selected from (Bl) paraquat, (B2) glyphosate, (B3) a sulfonyl urea, (B4) a chloroanilide or (BlO) a triketone, or their herbicidally effective salts.
3. A composition according to claim 1 in which R1 is methyl substituted with fluorine.
4. A composition according to claim 1 in which R1 is trifluoromethyl.
5. A composition according to claim 1 in which R2 is methyl or ethyl, more preferably methyl.
6. A composition according to claim 1 in which R3 is -CH2COOCH2CH3
7. A composition according to claim 1 in which X1 and X2 are independently chlorine or fluorine.
8. A composition according to claim 1 in which X1 is fluorine and X2 is chlorine.
9. A method for controlling undesirable vegetation, comprising applying to the locus of such vegetation a herbicidally effective amount of a composition as claimed in claim 1.
10. A method for controlling undesireable vegetation comprising separately applying to the locus of such vegetation herbicides (A) and (B) as defined in claim 1
PCT/GB2005/004468 2004-12-06 2005-11-21 Herbicidal composition Ceased WO2006061562A1 (en)

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MX2007006425A MX2007006425A (en) 2004-12-06 2005-11-21 Herbicidal composition.
US11/720,614 US20090233796A1 (en) 2004-12-06 2005-11-21 Herbicidal composition
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GB0503346.9 2005-02-17

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EP2092825A1 (en) 2008-02-21 2009-08-26 Bayer CropScience Aktiengesellschaft Herbicidal combinations comprising a herbicide of the class of the diamino-s-triazines
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US9414593B2 (en) 2006-10-27 2016-08-16 Syngenta Crop Protection, Llc Herbicidal compositions
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EP2147600A1 (en) 2008-07-21 2010-01-27 Bayer CropScience AG Method for weed control in lawn
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