WO2024099890A1 - Procédé de lutte contre les mauvaises herbes - Google Patents

Procédé de lutte contre les mauvaises herbes Download PDF

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Publication number
WO2024099890A1
WO2024099890A1 PCT/EP2023/080635 EP2023080635W WO2024099890A1 WO 2024099890 A1 WO2024099890 A1 WO 2024099890A1 EP 2023080635 W EP2023080635 W EP 2023080635W WO 2024099890 A1 WO2024099890 A1 WO 2024099890A1
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compound
hydrogen
methyl
fluoro
group
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PCT/EP2023/080635
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English (en)
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Ian Henry Aspinall
Elizabeth Catherine FRYE
Sean NG
William Guy Whittingham
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Syngenta Crop Protection Ag
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Publication of WO2024099890A1 publication Critical patent/WO2024099890A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
    • C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
    • C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40—Unsaturated compounds
    • C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals

Definitions

  • the present invention relates to the use of certain compounds as herbicides, to herbicidal compositions which comprise the compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.
  • the present invention is based on the finding that certain fluoromethyl phenylacetic acids of formula (I) as defined herein, exhibit surprisingly good herbicidal activity.
  • a compound of Formula (I) wherein:
  • R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, halogen, amino, cyano, nitro, hydroxyl, Ci. 5 alkyl, Cs-ecycloalkyl, Ci.2haloalkyl, cyanomethyl, halophenyl, Ci-
  • R 1 and R 2 together with the carbon atoms to which they are attached form a 5- or 6-membered ring, which may optionally be substituted by one or more groups selected from halogen, cyano, hydroxyl, Ci-salkyl, Ci-2haloalkyl, and Ci-4alkoxy, and wherein the 6-membered ring contains zero, one or two nitrogen atoms and wherein the 5-membered ring contains one or two heteroatoms independently selected from the group consisting of nitrogen and oxygen;
  • R 6 is selected from the group consisting of hydrogen, Ci-ealkyl and arylCi-2alkyl. or an agronomically acceptable salt of said compound. According to a second aspect of the invention, there is provided the use of a compound of Formula I as a herbicide.
  • an agrochemical composition comprising a herbicidally effective amount of a compound of formula (I) and an agrochemically-acceptable diluent or carrier.
  • Such an agricultural composition may further comprise at least one additional active ingredient.
  • a method of controlling or preventing undesirable plant growth wherein a herbicidally effective amount of a compound of formula (I), or a composition comprising this compound as active ingredient, is applied to the plants, to parts thereof or the locus thereof.
  • halogen refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.
  • cyano means a -CN group.
  • hydroxy or hydroxyl means an -OH group.
  • nitro means an -NO2 group.
  • amino means an -NH2 group.
  • C1-C5 alkyl refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from one to five carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Ci-Csalkyl and Ci-C2alkyl are to be construed accordingly.
  • Examples of Ci-Csalkyl include, but are not limited to, methyl (Me), ethyl (Et), n-propyl, 1-methylethyl (iso-propyl), n- butyl, and 1 -dimethylethyl (f-butyl).
  • C3-8 cycloalkyl refers to a stable, monocyclic ring radical which is saturated and contains 3 to 8 carbon atoms.
  • Cs-ecycloalkyl is to be construed accordingly.
  • Examples of Cs-scycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • C1-C4 alkoxy refers to a radical of the formula -OR a where R a is a Ci.C4alkyl radical as generally defined above.
  • C1-C2 alkoxy is to be construed accordingly.
  • Examples of Ci.4alkoxy include, but are not limited to, methoxy, ethoxy, propoxy, iso-propoxy and t-butoxy.
  • C1.4 alkoxyCi.4alkyl refers to a radical of the formula Rb-O-Ra- wherein Rb is a Ci-4alkyl radical as generally defined above, and Ra is a Ci.4alkylene radical as generally defined above.
  • C1-C2 haloalkyl refers to a Ci-C2alkyl radical as generally defined above substituted by one or more of the same or different halogen atoms. C2haloalkyl is to be construed accordingly.
  • Examples of Ci-C2haloalkyl include, but are not limited to chloromethyl, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl and 2,2,2-trifluoroethyl.
  • C2-C3 alkenyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one double bond that can be of either the (E)- or ( ⁇ -configuration, having from two to three carbon atoms, which is attached to the rest of the molecule by a single bond.
  • Examples of C ⁇ Csalkenyl include, but are not limited to ethenyl, prop-1 -enyl and allyl (prop-2-enyl).
  • C2-C3 alkynyl refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having from two to three carbon atoms, and which is attached to the rest of the molecule by a single bond.
  • Examples of C2-C3alkynyl include, but are not limited to ethynyl, prop-1 -ynyl and propargyl (prop-2-ynyl).
  • C1-C2 haloalkoxy refers to a Ci-C2alkoxy group as defined above substituted by one or more of the same or different halogen atoms.
  • Examples of C1- C2haloalkoxy include, but are not limited to fluoromethoxy, difluoromethoxy, fluoroethoxy, trifluoromethoxy and trifluoroethoxy.
  • C1.2 alkylsulfanyl refers to a radical of the formula -
  • R a is a Ci-2alkyl radical as generally defined above.
  • C1.2 alkylsulfinyl refers to a radical of the formula -
  • C1.2 alkylsulfonyl refers to a radical of the formula - S(0)2Ra wherein R a is a Ci-2alkyl radical as generally defined above.
  • Ci.2alkoxycarbonyl refers to a radical of the formula RaOC(O)-, wherein Ra is a Ci-2alkyl radical as generally defined above.
  • Ci-salkoxycarbonylCi-salkyl refers to a radical of the formula - RbC(O)OR a , wherein R a is a C1.3 alkyl radical as generally defined above and Rb is a Ci- salkylene radical as generally defined above.
  • arylCi.2alkyl refers to a aryl ring as defined above which is attached to the rest of the molecule by a Ci.2alkylene radical as defined above.
  • cyanoCi-ealkyl refers to a Ci-ealkyl radical as generally defined above substituted by one or more cyano groups. CyanoCi.4alkyl is to be construed accordingly. Examples of cyanoCi-ealkyl include, but are not limited to, cyanomethyl.
  • asymmetric carbon atoms in a compound of formula (I) means that the compounds may occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms. Also atropisomers may occur as a result of restricted rotation about a single bond.
  • Formula (I) is intended to include all those possible isomeric forms and mixtures thereof.
  • the present invention includes all those possible isomeric forms and mixtures thereof for a compound of formula (I) unless otherwise specified.
  • formula (I) is intended to include all possible tautomers (including lactam-lactim tautomerism and keto-enol tautomerism) where present.
  • the present invention includes all possible tautomeric forms for a compound of formula (I).
  • where there are di-substituted alkenes these may be present in E or Z form or as mixtures of both in any proportion.
  • the present invention includes all these possible isomeric forms and mixtures thereof for a compound of formula (I).
  • the compounds of formula (I) will typically be provided in the form of an agronomically acceptable salt, a zwitterion or an agronomically acceptable salt of a zwitterion.
  • This invention covers all such agronomically acceptable salts, zwitterions and mixtures thereof in all proportions.
  • Suitable agronomically acceptable salts of the present invention can be with cations that include but are not limited to, metals, conjugate acids of amines and organic cations.
  • suitable metals include aluminium, calcium, cesium, copper, lithium, magnesium, manganese, potassium, sodium, iron and zinc.
  • Suitable amines include allylamine, ammonia, amylamine, arginine, benethamine, benzathine, butenyl-2-amine, butylamine, butylethanolamine, cyclohexylamine, decylamine, diamylamine, dibutylamine, diethanolamine, diethylamine, diethylenetriamine, diheptylamine, dihexylamine, diisoamylamine, diisopropylamine, dimethylamine, dioctylamine, dipropanolamine, dipropargylamine, dipropylamine, dodecylamine, ethanolamine, ethylamine, ethylbutylamine, ethylenediamine, ethylheptylamine, ethyloctylamine, ethylpropanolamine, heptadecylamine, heptylamine, hexadecylamine, he
  • Suitable organic cations include benzyltributylammonium, benzyltrimethylammonium, benzyltriphenylphosphonium, choline, tetrabutylammonium, tetrabutylphosphonium, tetraethylammonium, tetraethylphosphonium, tetramethylammonium, tetramethylphosphonium, tetrapropylammonium, tetrapropylphosphonium, tributylsulfonium, tributylsulfoxonium, triethylsulfonium, triethylsulfoxonium, trimethylsulfonium, trimethylsulfoxonium, tripropylsulfonium and tripropylsulfoxonium.
  • the agrochemically acceptable salt is selected from the group consisting of sodium, potassium, aluminium, dimethylamine (DMA), diglycolamine (DGA) and choline salt.
  • the agrochemically acceptable salt is choline salt.
  • R 1 is selected from the group consisting of hydrogen, halogen, amino, cyano, nitro, hydroxyl, Ci-4alkyl, C ⁇ cycloalkyl, Ci.2haloalkyl, Ci.4alkoxy, Ci.2haloalkoxy, C ⁇ alkenyl, C2- salkynyl, halophenyl and Ci.2alkylsulfanyl, more preferably hydrogen, fluorine, chlorine, bromine, amino, cyano, Ci-4alkyl, cyclopropyl, halomethyl, Ci-salkoxy, Ci haloalkoxy, vinyl, ethynyl and methylsulfanyl, most preferably chlorine, bromine, cyano, methyl, ethyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, vinyl and ethynyl.
  • R 2 is selected from the group consisting of hydrogen, halogen, amino, cyano, nitro, hydroxyl, Ci-4alkyl, C ⁇ cycloalkyl, Ci.2haloalkyl, Ci.4alkoxy, Ci.2haloalkoxy, C ⁇ alkenyl, C2- salkynyl, halophenyl and Ci.2alkylsulfanyl, more preferably hydrogen, fluorine, chlorine, bromine, cyano, Ci-4alkyl, cyclopropyl, halomethyl, Ci-salkoxy, Ci haloalkoxy, vinyl, ethynyl, fluorophenyl and methylsulfanyl, most preferably hydrogen, chlorine, bromine, cyano, methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, vinyl and ethynyl.
  • R 1 and R 2 are both halogen, advantageously R 1 and R 2 are selected from chlorine and/or bromine.
  • R 3 to R 5 are preferably each hydrogen, and when both R 1 and R 2 are each chlorine, the enantiomer is in the form of the (R) or the (S) enantiomer.
  • R 1 and R 2 together with the carbon atoms to which they are attached form a 5- membered ring containing one or two heteroatoms independently selected from the group consisting of nitrogen and oxygen, more preferably the 5-membered ring contains two oxygen atoms.
  • the 5-membered ring is partially saturated, most preferably the 5-membered ring is saturated.
  • the 5-membered ring is substituted by one or two substituents independently selected from the group consisting of fluorine, chlorine and methyl, more preferably the 5-membered ring is substituted by two fluorine.
  • R 1 and R 2 together with the carbon atoms to which they are attached form a 6- membered ring containing zero, one or two nitrogen atoms, more preferably the 6-membered ring contains zero or one nitrogen, with the proviso that any nitrogen in the 6-membered ring is next to the benzene ring in structure (I).
  • the 6-membered ring is aromatic.
  • the 6-membered ring is substituted by zero or one substituent. If substituted, the substituent is preferably chlorine.
  • the 6-membered ring contains one nitrogen and has one chlorine substituent and R 3 to R 5 are each hydrogen.
  • R 3 is selected from the group consisting of hydrogen, halogen, amino, cyano, hydroxyl, Ci-Csalkyl, Ci.2haloalkyl, Ci-C4alkoxy, C2-Csalkenyl, C2-Csalkynyl, Ci-C2haloalkoxy and halophenyl, more preferably hydrogen, halogen, amino, trifluoromethoxy, trifluoromethyl, methyl, tert-butyl and methoxy, most preferably hydrogen, fluorine and chlorine.
  • R 4 is selected from the group consisting of hydrogen, amino, fluorine, chlorine, methoxy, more preferably hydrogen.
  • R 5 is selected from the group consisting of hydrogen, fluorine, chlorine, amino, nitro and methoxy, more preferably hydrogen, chlorine and methoxy.
  • R 6 is selected from the group consisting of hydrogen, Ci-Csalkyl and benzyl, more preferably hydrogen.
  • R 3 is trifluoromethyl
  • R 1 , R 2 , R 4 and R 5 are each hydrogen.
  • R 1 is methyl
  • R 2 is either cyano or methoxy
  • R 3 to R 5 are each hydrogen.
  • a compound of Formula I as a herbicide, where R 1 and R 2 are substituted as above and R 3 to R 5 are each hydrogen.
  • R 1 is methyl and R 2 is a halogen, preferably chlorine.
  • Table 1 below discloses 819 specific compounds of formula (I), designated compound numbers 1-1 to 1-819 respectively, wherein R 6 is hydrogen.
  • a compound of formula (A), wherein R6 represents methyl or ethyl may be treated with a base, such as lithium hydroxide, in a suitable solvent such as a mixture of methanol and water.
  • a base such as lithium hydroxide
  • Compounds of formula (A) may be prepared from compounds of formula (B) as shown in reaction scheme 2.
  • a mixture of a compound of formula (B), wherein R6 represents methyl or ethyl, in a suitable solvent such as tetra hydrofuran, may be treated with a base such as lithium diisopropylamide, followed by a methylating reagent such as iodomethane.
  • a mixture of a compound of formula (C), wherein X represents iodo or bromo, and a compound of formula (D), wherein R6 represents methyl or ethyl may be treated with a catalyst such as nickel(ll) iodide, a ligand such as 5,5’-dimethyl-2,2’-bipyridine, a metal such as zinc and a metallic species such as dichloromagnesium in a suitable solvent such as N,N- dimethylacetamide.
  • a catalyst such as nickel(ll) iodide, a ligand such as 5,5’-dimethyl-2,2’-bipyridine, a metal such as zinc and a metallic species such as dichloromagnesium in a suitable solvent such as N,N- dimethylacetamide.
  • Aryl halides of formula (C) are commercially available or may be prepared by methods well known in the literature.
  • a compound of formula (E), wherein R6 represents methyl or ethyl may be treated with a base such as sodium bis(trimethylsilyl)amide, followed by a fluorinating reagent such as /V-fluorobenzenesulfonimide, in a suitable solvent such as tetrahydrofuran.
  • a base such as sodium bis(trimethylsilyl)amide
  • a fluorinating reagent such as /V-fluorobenzenesulfonimide
  • a compound of formula (E), wherein R6 represents methyl or ethyl may be treated with a base such as lithium diisopropylamide, followed by a methylating reagent such as methyl iodide, in a suitable solvent such as tetra hydrofuran.
  • a base such as lithium diisopropylamide
  • a methylating reagent such as methyl iodide
  • a compound of formula (G), wherein R6 represents methyl or ethyl may be treated with a fluorinating reagent such as diethylaminosulfur trifluoride, in a suitable solvent such as dichloromethane.
  • a fluorinating reagent such as diethylaminosulfur trifluoride
  • a compound of formula (H), wherein R6 represents methyl or ethyl may be treated with a fluorinating reagent such as diethylaminosulfur trifluoride, in a suitable solvent such as dichloromethane.
  • a fluorinating reagent such as diethylaminosulfur trifluoride
  • a compound of formula (J), wherein R6 represents methyl or ethyl may be treated with a methylating reagent such as methylmagnesium bromide, in a suitable solvent such as tetrahydrofuran.
  • a methylating reagent such as methylmagnesium bromide
  • the compounds according to the invention can be used as herbicidal agents in unmodified form, but they are generally formulated into compositions 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.
  • soluble liquids soluble liquids, water-soluble concentrates or water soluble granules are preferred.
  • 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. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight.
  • the active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution.
  • the encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art.
  • very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.
  • the formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known perse.
  • liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2- dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, /V,/V-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane
  • 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.
  • Surface-active 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.
  • compositions 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.
  • Preferred oil additives comprise alkyl esters of C8-C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively).
  • Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10 th Edition, Southern Illinois University, 2010.
  • the herbicidal compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, compounds of formula (I) 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.
  • the inventive compositions generally comprise from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compounds of the present invention 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. Whereas commercial products may preferably be formulated as concentrates, the end user will normally employ dilute formulations.
  • the rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pest to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • a general guideline compounds may be applied at a rate of from 1 to 2000 l/ha, especially from 10 to 1000 l/ha.
  • Preferred formulations can have the following compositions (weight %): Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %
  • Dusts active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %
  • Suspension concentrates active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 %
  • 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 %
  • composition of the present may further comprise at least one additional pesticide.
  • additional pesticide is a herbicide and/or herbicide safener.
  • the compounds 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, bromacil, bromoxynil, butachlor, butafenacil, carfentrazone (including carfentrazone-ethyl), cloransulam (including cloransulam-methyl), chlorimuron (including chlorimuron-ethyl), chlorotoluron, chlorsulfuron, cinmethylin,
  • the mixing partners of the compound of formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, Fourteenth Edition, British Crop Protection Council, 2006.
  • the compound of formula (I) can also be used in mixtures with other agrochemicals such as fungicides, nematicides or insecticides, examples of which are given in The Pesticide Manual.
  • the mixing ratio of the compound of formula (I) to the mixing partner is preferably from 1 : 100 to 1000:1.
  • mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient” relates to the respective mixture of compound of formula (I) with the mixing partner).
  • herbicide safeners examples include benoxacor, cloquintocet (including cloquintocetmexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlora zoleethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifenethyl), mefenpr (in eluding mefenpyr-diethyl), metcamifen and oxabetrinil.
  • herbicide safeners examples include benoxacor, cloquintocet (including cloquintocetmexyl), cyprosulfamide, dichlormid, fenchlorazole (including fenchlora zoleethyl), fenclorim, fluxofenim, furilazole, isoxadifen (including isoxadifenethyl), mefenpr (in
  • the safeners of the compound of formula (I) may also be in the form of esters or salts, as mentioned e.g. in The Pesticide Manual, 14 th Edition (BCPC), 2006.
  • the reference to cloquintocet-mexyl also applies to a lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salt thereof as disclosed in WO 02/34048, and the reference to fenchlorazole-ethyl also applies to fenchlorazole, etc.
  • the mixing ratio of compound of formula (I) to safener is from 100:1 to 1 :10, especially from 20: 1 to 1 : 1 .
  • mixtures can advantageously be used in the above-mentioned formulations (in which case "active ingredient” relates to the respective mixture of compound of formula (I) with the safener).
  • the compounds of formula (I) of this invention are useful as herbicides.
  • the present invention therefore further comprises a method for controlling unwanted plants comprising applying to the said plants or a locus comprising them, an effective amount of a compound of the invention or a herbicidal composition containing said compound.
  • Controlling means killing, reducing or retarding growth or preventing or reducing germination.
  • the plants to be controlled are unwanted plants (weeds).
  • Locus means the area in which the plants are growing or will grow.
  • the rates of application of compounds of formula (I) may vary within wide limits and depend on the nature of the soil, the method of application (pre-emergence; post-emergence; application to the seed furrow; no tillage application etc.), the crop plant, the weed(s) to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.
  • the compounds of formula (I) according to the invention are generally applied at a rate of from 10 to 2000 g/ha, especially from 50 to 1000 g/ha. A preferred range is 10-200g/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.
  • Useful plants in which the composition according to the invention can be used include crops such as cereals, for example barley and wheat, cotton, oilseed rape, sunflower, maize, rice, soybeans, sugar beet, sugar cane and turf.
  • Crop plants can also include trees, such as fruit trees, palm trees, coconut trees or other nuts. Also included are vines such as grapes, fruit bushes, fruit plants and vegetables.
  • 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.
  • herbicides or classes of herbicides e.g. ALS-, GS-, EPSPS-, PPO-, ACCase- and HPPD- inhibitors
  • 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 maize varieties 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 are also to be understood to include those which are obtained by conventional methods of breeding or genetic engineering and contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).
  • output traits e.g. improved storage stability, higher nutritional value and improved flavour.
  • Compounds of formula (I) and compositions of the invention can typically be used to control a wide variety of monocotyledonous and dicotyledonous weed species.
  • Examples of monocotyledonous species that can typically be controlled include Alopecurus myosuroides, Avena fatua, Brachiaria plantag inea, Bromus tectorum, Cyperus esculentus, Digitaria sanguinalis, Echinochloa crus-galli, Lolium perenne, Lolium multiflorum, Panicum miliaceum, Poa annua, Setaria viridis, Setaria faberi and Sorghum bicolor
  • Examples of dicotyledonous species that can be controlled include Abutilon theophrasti, Amaranthus retroflexus, Bidens pilosa, Chenopodium album, Euphorbia heterophylla, Galium aparine, Ipomoea hederacea, Kochia scoparia, Polygonum convolvulus, Sida spinosa, Sinapis arvensis, Solanum nigrum, Stellaria media, Veronica persica and Xanthium strumarium.
  • the compounds of formula (I) are also useful for pre-harvest desiccation in crops, for example, but not limited to, potatoes, soybean, sunflowers and cotton.
  • Pre-harvest desiccation is used to desiccate crop foliage without significant damage to the crop itself to aid harvesting.
  • Compounds/compositions of the invention are particularly useful in non-selective burn-down applications, and as such may also be used to control volunteer or escape crop plants.
  • Step 1 Synthesis of ethyl 2-fluoro-2-(3-methoxy-2-methyl-phenyl)acetate
  • 1-iodo-3-methoxy-2-methyl-benzene 901 mg, 3.63 mmol
  • 5,5’-dimethyl-2,2’-bipyridine 0.363 mmol, 67 mg
  • dichloromagnesium 519 mg, 5.45 mmol
  • zinc 713 mg, 10.9 mmol
  • diiodonickel 114 mg, 0.363 mmol.
  • the flask was evacuated and back filled with nitrogen (x 3) then /V,/V-dimethylacetamide (4 mL/mmol) was added.
  • methyl 2-(2-chloro-4-fluoro-phenyl)acetate (1 .05 g, 5.08 mmol).
  • the flask was evacuated and backfilled with nitrogen three times, before the addition of tetra hydrofuran (24 mL).
  • the colourless solution was cooled to -78 °C.
  • Lithium diisopropylamide (2.0 mol/L, 2.7 mL, 5.4 mmol) was added dropwise and the reaction was stirred at -78 °C for 30 minutes.
  • Methyl iodide (0.34 mL, 5.4 mmol) was added to the reaction mixture and the reaction mixture was allowed to warm to room temperature and stirred for 3 hours.
  • methyl 2-(2-chloro-4-fluoro- phenyl)propanoate 0.817 g, 3.58 mmol.
  • the flask was evacuated and backfilled with nitrogen three times, before the addition of tetra hydrofuran (15 mL).
  • the solution was cooled to -78 °C and sodium bis(trimethylsilyl)amide (1.0 mol/L in THF, 3.9 mL, 3.9 mmol) was added dropwise to the stirred solution.
  • reaction was stirred at -78 °C for 30 minutes before addition of /V- fluorobenzenesulfonimide (1.24 g, 3.95 mmol) in tetrahydrofuran (6 mL).
  • the reaction mixture was stirred for 30 minutes before being allowed to warm to room temperature.
  • the reaction was stirred for 3 hours and then quenched with water.
  • the reaction mixture was extracted with ethyl acetate (3 x 10 mL).
  • Diethylaminosulfur trifluoride (1.30 g, 7.68 mmol) was added to a solution of ethyl 2-(4- bromophenyl)-2-hydroxy-propanoate (1.75 g, 6.40 mmol) in dry dichloromethane (13 mL) at 0°C under an argon atmosphere. The resulting mixture was stirred at 0°C for 20 minutes. Saturated aqueous NaHCCh solution (15 mL) was carefully added. The organic phase was separated, washed with water (20 mL), dried with Na2SO4 and concentrated under vacuum.
  • Step 2 Synthesis of methyl 2-(3-chloro-2-ethyl-phenyl)-acetate
  • Thionyl chloride (1.8 ml, 25 mmol) was added dropwise to a stirred solution of 2-(3-chloro-2- ethyl-phenyl)-acetic acid (0.79 g, 4.0 mmol) in methanol (10 ml).
  • the resulting mixture was stirred at ambient temperature for 10 minutes, then concentrated under reduced pressure and purified by reverse phase chromatography, eluting with 50-100% acetonitrile in water plus 0.1% formic acid, to provide methyl 2-(3-chloro-2-ethyl-phenyl)-acetate as a pale oil (635 mg).
  • a number of compounds of the invention for example 1-074 and 2-181 , are obtainable as of the priority date of the present application from commercial sources, such as Enamine.
  • aqueous spray solution derived from the formulation of the technical active ingredient in a small amount of acetone and a special solvent and emulsifier mixture referred to as IF50 (11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether), to create a 50g/l solution which was then diluted using 0.2% Genapol XO80 as diluent to give the desired final dose of test compound.
  • IF50 11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether
  • aqueous spray solution derived from the formulation of the technical active ingredient in a small amount of acetone and a special solvent and emulsifier mixture referred to as IF50 (11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether), to create a 50g/l solution which was then diluted using 0.2% Genapol XO80 as diluent to give the desired final dose of test compound.
  • IF50 11.12% Emulsogen EL360 TM + 44.44% N-methylpyrrolidone + 44.44% Dowanol DPM glycol ether

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Abstract

L'invention concerne un composé de formule I, dans laquelle : R1, R2, R3, R4 et R5 sont indépendamment choisis dans le groupe constitué par hydrogène, halogène, amino, cyano, nitro, hydroxyle, alkyle en C1-5, cycloalkyle en C3-6, haloalkyle en C1-2, cyanométhyle, alcoxy en C1-2 alkyle en C1-2, alcoxy en C1-4, haloalcoxy en C1-2, alcényle en C2-3, alcynyle en C2-3, halophényle, alcoxycarbonyle en C1-2, alkylsulfanyle en C1-2, alkylsulfinyle en C1-2 et alkylsulfonyle en C1-2 ; ou R1 et R2 conjointement avec les atomes de carbone auxquels ils sont fixés forment un cycle à 5 ou 6 chaînons, qui peut éventuellement être substitué par un ou plusieurs groupes choisis parmi halogène, cyano, hydroxyle, alkyle en C1-5, haloalkyle en C1-2 et alcoxy en C1-4, et le cycle à 6 chaînons contenant zéro, un ou deux atomes d'azote et le cycle à 5 chaînons contenant un ou deux hétéroatomes indépendamment choisis dans le groupe constitué par l'azote et l'oxygène ; R6 est choisi dans le groupe constitué par hydrogène, alkyle en C1-6 et arylalkyle en C1-2, ou un sel agronomiquement acceptable dudit composé.
PCT/EP2023/080635 2022-11-10 2023-11-03 Procédé de lutte contre les mauvaises herbes WO2024099890A1 (fr)

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