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WO1998051153A1 - Procedes et derives herbicides - Google Patents

Procedes et derives herbicides Download PDF

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Publication number
WO1998051153A1
WO1998051153A1 PCT/EP1998/003159 EP9803159W WO9851153A1 WO 1998051153 A1 WO1998051153 A1 WO 1998051153A1 EP 9803159 W EP9803159 W EP 9803159W WO 9851153 A1 WO9851153 A1 WO 9851153A1
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WO
WIPO (PCT)
Prior art keywords
formula
compound
compounds
active material
per hectare
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP1998/003159
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English (en)
Inventor
Susan Mary Cramp
Russell J. Outcalt
Ashley Slater
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Agriculture Ltd
Original Assignee
Rhone Poulenc Agriculture Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from GBGB9709831.3A external-priority patent/GB9709831D0/en
Priority claimed from GBGB9709829.7A external-priority patent/GB9709829D0/en
Application filed by Rhone Poulenc Agriculture Ltd filed Critical Rhone Poulenc Agriculture Ltd
Priority to AU79164/98A priority Critical patent/AU7916498A/en
Publication of WO1998051153A1 publication Critical patent/WO1998051153A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C07C317/46—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members 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
    • C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Definitions

  • This invention relates to a method for the control of weeds, to novel 4-benzoylisoxazole derivatives and 2-cyano-l, 3-dione derivatives, compositions containing them, processes for their preparation, intermediates in their preparation and their use as herbicides.
  • Herbicidal 4-benzoylisoxazoles are described in European Patent Publication Numbers 0418175, 0487357, 0527036, 0527037, 0560482, 0560483 and 0682659.
  • WO 95/22903 discloses a number of 4- benzoylisoxazole derivatives useful for the control of pests and specifically discloses 5- cyclopropyl -4 - ( 4 - fluoro- 3 -methoxy- 2 - methylsulphinylbenzoyl) isoxazole and methyl 5- cyclopropy1 -4 - (4 - fluoro- 3 -methoxy- 2 - methylsulphinylbenzoyl) isoxazole-3 -carboxylate of general formula (I) .
  • This publication however contains no suggestion whatsoever that these compounds possess useful herbicidal activity.
  • Herbicidal 2-cyano-l , 3-dione derivatives are described in European Patent Publication Numbers 0213892, 0496630 and 0496631, and International Patent Publication No. WO 95/25099.
  • the present invention accordingly provides a method for controlling the growth of weeds (ie undesired vegetation) at a locus which comprises applying to the locus a herbicidally effective amount of at least one compound which is a benzoyl derivative of formula (I) :
  • A represents a group of formula D or E:
  • R 1 represents a straight or branched chain alkyl group containing from one to six (for example one to four) carbon atoms; and n represents 0, 1 or 2 ; or when A represents a group (E) , an agriculturally acceptable salt or metal complex thereof .
  • salts the cations of which are known and accepted in the art for the formation of salts for agricultural or horticultural use.
  • the salts are water-soluble.
  • Suitable salts with bases include alkali metal (eg. sodium and potassium) , alkaline earth metal (eg. calcium and magnesium) , ammonium and amine (eg. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts.
  • alkali metal eg. sodium and potassium
  • alkaline earth metal eg. calcium and magnesium
  • ammonium and amine eg. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine
  • metal complexes compounds in which one or both of the oxygen atoms of a 1, 3-dione of formula (I) wherein A represents a group (E) , act as chelating agents to a metal cation.
  • metal cations include zinc, manganese, cupric, cuprous, ferric, ferrous, titanium and aluminium.
  • the present invention also provides benzoyl derivatives of formula (I) with the proviso that when R represents hydrogen or -CU2Me, n is not
  • the compounds of the invention show improved activity against maize and soya weeds especially Setaria species eg Setaria faberii, Setaria viridis and Abutilon theophrasti at low rates of application, and also show high levels of selectivity in soya (especially pre -emergence) in comparison with known compounds .
  • A represents (D) ;
  • X represents 2S (O) n Me-30Me-4F; R represents hydrogen or -CO2R 1 ; and
  • R 1 represents methyl or ethyl .
  • a further preferred class of compounds of formula (I) are those in which:
  • A represents (D) ;
  • X represents 2S (O) n Me-30Me-4F; and
  • n represents 2.
  • the invention also provides compounds of formulae (la) :
  • R 1 represents a straight or branched chain alkyl group containing from one to six (for example one to four) carbon atoms; and n represents 0, 1 or 2 ; and a compound of formula (lb) :
  • the most preferred compound of formula (I) is 5-cyclopropyl-4- (4-fluoro-3 -methoxy-2 - methylsulphonylbenzoyl) isoxazole, hereinafter referred to as compound 1.
  • Another more preferred compound of formula (I) is ethyl 5-cyclopropyl-4- (4-fluoro-3 - methoxy-2 -methylsulphonylbenzoyl) isoxazole-3- carboxylate (compound 4) .
  • L is a leaving group and X is as hereinbefore defined, with hydroxylamine or a salt of hydroxylamine.
  • Hydroxylamine hydrochloride is generally preferred.
  • L is alkoxy, for example ethoxy, or N,N- dialkylamino, for example dimethylamino, the alkyl portions of which comprise a straight- or branched- chain C x to C 6 alkyl group.
  • the reaction is generally carried out in an organic solvent such as ethanol or acetonitrile or a mixture of a water-miscible organic solvent and water, preferably in a ratio of organic solvent: water of from 1:99 to 99:1, optionally in the presence of a base or acid acceptor such as triethylamine or sodium acetate at a temperature from room temperature to the boiling point of the solvent .
  • organic solvent such as ethanol or acetonitrile or a mixture of a water-miscible organic solvent and water, preferably in a ratio of organic solvent: water of from 1:99 to 99:1, optionally in the presence of a base or acid acceptor such as triethylamine or sodium acetate at a temperature from room temperature to the boiling point of the solvent .
  • X is as defined above may be prepared by the reaction of an alkaline metal or alkali earth metal salt of compounds of formula (III) :
  • (III) is generally prepared in situ by treating the compound of formula (III) with a base.
  • suitable bases include alkaline earth metal alkoxides such as magnesium methoxide .
  • Intermediates of formula (III) are novel and as such form a further feature of the invention.
  • compounds of formula (I) wherein A represents (E) and X is as defined above may be prepared by the reaction of the corresponding compound of formula (I) wherein A represents (D) and R represents hydrogen, with a base, for example alkali or alkaline earth metal hydroxides, alkoxides such as sodium ethoxide or organic bases such as triethylamine.
  • Solvents may be alcohols such as methanol or chlorinated hydrocarbons such as dichloromethane which are particularly suitable when organic bases are used.
  • the reaction is generally performed at a temperature of from 20°C to the reflux temperature of the solvent .
  • compounds of formula (I) in which A represents (E) may be prepared by the reaction of a compound of formula (IV) :
  • the reaction is generally performed in the presence of a base, in a solvent or solvent mixture.
  • bases include metal hydrides, hydroxides or alkoxides (e.g. sodium or lithium hydride, sodium hydroxide, potassium hydroxide, magnesium ethoxide or magnesium methoxide) .
  • Suitable solvents include for example tetrahydrofuran; hydrocarbons such as toluene; or halogenated hydrocarbons such as dichloromethane.
  • the reaction is generally performed at a temperature from 0°C to the reflux temperature.
  • compounds of formula (I) in which A represents (E) may also be prepared by the reaction of an acid chloride of formula (VI) :
  • (VIII) may be carried out in the presence of a mild base such as an organic base e.g. triethylamine, in an inert solvent such as acetonitrile or dichloromethane at a temperature between room temperature and the reflux temperature of the mixture .
  • a mild base such as an organic base e.g. triethylamine
  • an inert solvent such as acetonitrile or dichloromethane
  • the rearrangement of the intermediate of formula (VIII) to the compound of formula (I) in which A represents a group (E) is generally carried out _n situ in an inert solvent such as acetonitrile or dichloromethane in the presence of a catalyst such as a source of cyanide.
  • sources of cyanide are acetone cyanohydrin or an alkali metal cyanide such as potassium cyanide, optionally in the presence of a crown ether such as 18-crown-6.
  • compounds of formula (I) in which A represents (E) may be prepared by the reaction of an acid chloride of formula (VI) , with a beta-ketonitrile of formula (VII) via an intermediate of formula (IX) :
  • compounds of formula (I) in which n represents one or two may be prepared by the oxidation of the sulphur atom of the corresponding compounds of formula (I) in which n is zero or one.
  • the oxidation of the sulphur atom is generally carried out using for example 3-chloroperoxybenzoic acid in an inert solvent such as dichloromethane at a temperature from -40°C to room temperature.
  • Compounds of formula (II) may be prepared by the reaction of compounds of formula (III) above with either a trialkyl orthoformate such as triethyl orthoformate or a dimethylformamide dialkyl acetal such as dimethylformamide dimethyl acetal, the alkyl portions of which comprise a straight- or branched- chain C x to C 6 alkyl group .
  • a trialkyl orthoformate such as triethyl orthoformate
  • a dimethylformamide dialkyl acetal such as dimethylformamide dimethyl acetal
  • reaction with a trialkyl orthoformate can be carried out in the presence of acetic anhydride at the reflux temperature of the mixture and the reaction with dialkylformamide dialkyl acetal is carried out optionally in the presence of an inert solvent at a temperature from room temperature to the reflux temperature of the mixture .
  • the reaction is generally performed in a solvent such as ether, tetrahydrofuran or N,N- dimethylformamide, in the presence of a base, preferably an alkali metal base such as sodium hydride, at a temperature from 0°C to the reflux temperature .
  • a base preferably an alkali metal base such as sodium hydride
  • Acid chlorides of formula (IV) may be prepared by the reaction of benzoic acids of formula (XIII) :
  • Hydroxylamine hydrochloride (1.67g) and sodium acetate (1.3g) were added to a stirred solution of 3 -cyclopropyl -2 -ethoxymethylene- 1- (4 -fluoro- 3 -methoxy- 2 - methylsulphonylphenyl)propan-l, 3-dione (6.1g) in ethanol . After 1 hour the solvent was evaporated, and the residue in ethyl acetate was washed (water) , dried (magnesium sulphate) and evaporated.
  • EXAMPLE 2 m-Chloroperbenzoic acid (1.12g of 90% w/w in water) was added at -20°C to a stirred solution of 5 -cyclopropyl -4- (4-fluoro- 3 -methoxy- 2- methylthiobenzoyl) isoxazole (2.0g) in dichloromethane. A further addition of m- chloroperbenzoic acid (0.4g) was made after 1 hour, and after 3 hours the mixture was filtered and evaporated.
  • the compounds of formula (I) are normally used in the form of herbicidal compositions (i.e. in association with compatible diluents or carriers and/or surface active agents suitable for use in herbicidal compositions) , for example as hereinafter described.
  • the compounds of formula (I) show herbicidal activity against dicotyledonous (i.e. broad- leafed) and monocotyledonous (i.e. grass) weeds by pre- and/or post-emergence application.
  • pre-emergence application application to the soil in which the weed seeds or seedlings are present before emergence of the weeds above the surface of the soil .
  • post-emergence application application to the aerial or exposed portions of the weeds which have emerged above the surface of the soil.
  • the compounds of formula (I) may be used to control the growth of : broad-leafed weeds, for example, Abutilon theophrasti, Amaranthus hybridus , Amaranthus retroflexus , Amaranthus rudis, Amaranthus tuberculatos , Ambrosia artemisiifolia. Ambrosia trifida, Bidens pilosa, Chenopodium album.
  • Convolvulus arvensis Datura ferox. Datura stramonium. Euphorbia spp, Galium aparine , Helianthus spp, Ipomoea spp . e.g. Ipomoea purpurea , amium sp , Matricaria spp, Plantago spp, Polygonum aviculare, Polygonum pennsylvanicum, Raphanus raphanistrum, Schkuhria pinnata, Sesbania exaltata, Sida rhombifolia, Sida spinosa, Sinapis arvensis, Solanum nigrum, Veronica hederaefolia, Veronica persica, and Xanthium strumarium, and grass weeds, for example Alopecurus myosuroides, Avena fatua, Brachiaria planta ⁇ inea, Cenchrus echinatus .
  • Cynodon dactylon Di ⁇ itaria horizontalis. Digitaria sanguinalis, Echinochloa crus-galli. Eragrostis virescens, Sorghum bicolor, Eleusine indica, Imperata cylindrica, Panicum dichotomiflorum. Panicum maximum, Panicum miliaceum, Pennisetum glaucum, Setaria spp, e.g. Setaria faberii, Setaria viridis, and Setaria italica. Sorghum halepense, and sedges, for example, Cyperus esculentus.
  • the amounts of compounds of formula (I) applied vary with the nature of the weeds, the compositions used, the time of application, the climatic and edaphic conditions and (when used to control the growth of weeds in crop-growing areas) the nature of the crops.
  • the rate of application should be sufficient to control the growth of weeds without causing substantial permanent damage to the crop.
  • application rates from 0.01kg to 1kg, preferably 0.01kg to 0.5kg, and more preferably 0.02kg to 0.25kg, of active material per hectare give good results.
  • higher or lower application rates may be used, depending upon the particular problem of weed control encountered.
  • the compounds of formula (I) When used to control the growth of weeds by pre-emergence application, the compounds of formula (I) may be incorporated into the soil in which the weeds are expected to emerge. It will be appreciated that when the compounds of formula (I) are used to control the growth of weeds by post-emergence application, i.e. by application to the aerial or exposed portions of emerged weeds, the compounds of formula (I) will also normally come into contact with the soil and may also then exercise a pre-emergence control on later-germinating weeds in the soil. Where especially prolonged weed control is required, the application of the compounds of formula (I) may be repeated if required.
  • the compounds of formula (I) may be used to controlselectively the growth of weeds, by application to a locus of weed infestation, which is an area used, or to be used, for growing crops, for example peas, beans, sunflowers, potatoes and especially soya or maize .
  • compositions suitable for herbicidal use comprising one or more of the compounds of formula (I) , in association with, and preferably homogeneously dispersed in, one or more compatible agriculturally- acceptable diluents or carriers and/or surface active agents [i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of formula (I)] .
  • compatible agriculturally- acceptable diluents or carriers and/or surface active agents i.e. diluents or carriers and/or surface active agents of the type generally accepted in the art as being suitable for use in herbicidal compositions and which are compatible with compounds of formula (I)
  • compositions in which the compounds of formula (I) are dissolved in or intimately mixed with other components.
  • the term "herbicidal compositions” is used in a broad sense to include not only compositions which are ready for use as herbicides but also concentrates which must be diluted before use.
  • the compositions contain from 0.05 to 90% by weight of one or more compounds of formula (I) .
  • the herbicidal compositions may contain both a diluent or carrier and surface-active (e.g. wetting, dispersing, or emulsifying) agent.
  • Surface-active agents which may be present in herbicidal compositions of the present invention may be of the ionic or non- ionic types, for example sulphoricinoleates, quaternary ammonium derivatives, products based on condensates of ethylene oxide with alkyl and polyaryl phenols, e.g.
  • nonyl- or octyl-phenols or carboxylic acid esters of anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, alkali and alkaline earth metal salts of sulphuric acid esters and sulphonic acids such as dinonyl- and dioctyl-sodium sulphonosuccinates and alkali and alkaline earth metal salts of high molecular weight sulphonic acid derivatives such as sodium and calcium lignosulphonates and sodium and calcium alkylbenzene sulphonates .
  • the herbicidal compositions according to the present invention may comprise up to 10% by weight, e.g. from 0.05% to 10% by weight, of surface-active agent but, if desired, herbicidal compositions according to the present invention may comprise higher proportions of surface-active agent, for example up to 15% by weight in liquid emulsifiable suspension concentrates and up to 25% by weight in liquid water soluble concentrates .
  • suitable solid diluents or carriers are aluminium silicate, talc, calcined magnesia, kieselguhr, tricalcium phosphate, powdered cork, absorbent carbon black and clays such as kaolin and bentonite .
  • the solid compositions (which may take the form of dusts, granules or wettable powders) are preferably prepared by grinding the compounds of formula (I) with solid diluents or by impregnating the solid diluents or carriers with solutions of the compounds of formula (I) in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders.
  • Granular formulations may be prepared by absorbing the compounds of formula (I) (dissolved in suitable solvents, which may, if desired, be volatile) onto the solid diluents or carriers in granular form and, if desired, evaporating the solvents, or by granulating compositions in powder form obtained as described above.
  • Solid herbicidal compositions particularly wettable powders and granules, may contain wetting or dispersing agents (for example of the types described above) , which may also, when solid, serve as diluents or carriers.
  • Liquid compositions according to the invention may take the form of aqueous, organic or aqueous-organic solutions, suspensions and emulsions which may incorporate a surface-active agent.
  • Suitable liquid diluents for incorporation in the liquid compositions include water, glycols, tetrahydrofurfuryl alcohol, acetophenone , cyclohexanone, isophorone, toluene, xylene, mineral, animal and vegetable oils and light aromatic and naphthenic fractions of petroleum (and mixtures of these diluents) .
  • Surface-active agents which may be present in the liquid compositions, may be ionic or non- ionic (for example of the types described above) and may, when liquid, also serve as diluents or carriers .
  • Powders, dispersible granules and liquid compositions in the form of concentrates may be diluted with water or other suitable diluents, for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • suitable diluents for example mineral or vegetable oils, particularly in the case of liquid concentrates in which the diluent or carrier is an oil, to give compositions ready for use.
  • liquid compositions of the compound of formula (I) may be used in the form of self-emulsifying concentrates containing the active substances dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substances, the simple addition of water to such concentrates producing compositions ready for use.
  • Liquid concentrates in which the diluent or carrier is an oil may be used without further dilution using the electrostatic spray technique .
  • Herbicidal compositions according to the present invention may also contain, if desired, conventional adjuvants such as adhesives, protective colloids, thickeners, penetrating agents, stabilisers, sequestering agents, anti- caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.
  • a further feature of the present invention is a herbicidally active mixture
  • a herbicidally active mixture comprising a compound of formula (I) in association with, and preferably homogeneously dispersed in, one or more other pesticidally active compounds and, if desired, one or more compatible pesticidally acceptable diluents or carriers, surface-active agents and conventional adjuvants as hereinbefore described.
  • the respective use rate ratio of these is generally in the range 1:20 to 5:1, preferably 1:10 to 3:1.
  • the application rate of the compound of formula (I) used in the mixtures is generally in the range 10-lOOOg, preferably 10-500g, more preferably 20-250g of active material per hectare.
  • Examples of other pesticidally active compounds which may be included in, or used in conjunction with, the herbicidal compositions of the present invention include herbicides, for example to increase the range of weed species controlled.
  • Examples of the partner herbicides which may be used and which form part of the present invention and the application rates which are generally used for these mixtures are as follows : acetochlor [2-chloro-N-ethoxymethyl-6 ' - ethylacet-o-toluidide] , used generally in the range of 100-4000g of active material per hectare; acifluorofen [5- (2-chloro- ⁇ , ⁇ , ⁇ - trifluoro-p-tolyloxy) -2-nitrobenzoic acid] , used generally in the range of 5-500g of active material per hectare; aclonifen [2-chloro-6- nitro-3-phenoxyaniline] , used generally in the range of 5-500g of active material per hectare; alachlor [2-chloro-2'
  • ET-751 [ethyl 2-chloro-5- (4-chloro-5-difluoromethoxy-1- methylpyrazol-3-yl) -4-fluorophenoxyacetate] , used generally in the range of 0.5-20g of active material per hectare; ethalfluralin [N-ethyl- ⁇ , ⁇ , ⁇ -trifluoro-N- (2-methylallyl) -2, 6-dinitro-p- toluidine] , used generally in the range of 200- 2000g of active material per hectare; fenoxaprop [ ( ⁇ ) -2- [4- (6-chloro-l, 3-benzoxazol-2- yloxy) phenoxy] propionic acid, used generally in the range of 10-150g of active material per hectare; flampropmethyl [methyl N-benzoyl-N- (3- chloro-4-fluorophenyl) -D-alaninate] , used generally in the range of
  • Preferred mixture partners are selected from acifluorofen; bentazone; chlorimuron; clethodim; clomazone; 2,4-D; glyphosate; imazethapyr; linuron; metribuzin; norflurazon; and trifluralin.
  • the above mixtures may be used for example to control the growth of the hereinbefore defined weed species.
  • Pesticidally active compounds and other biologically active materials which may be included in, or used in conjunction with, the herbicidal compositions of the present invention, for example those hereinbefore mentioned, and which are acids, may, if desired, be utilized in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • Example Cl illustrate herbicidal compositions according to the present invention.
  • An emulsifiable concentrate is formed from: Active ingredient (Compound 1) 20% w/v
  • CaDDBS Calcium dodecylbenzenesulphonate
  • Nonylphenol ethylene oxide propylene oxide condensate (Synperonic NPE 1800)
  • Aromatic solvent 4% w/v Aromatic solvent (Solvesso) to 100 volumes by stirring gamma butyrolactone, active ingredient (Compound 1) , CaDDBS, NPEOPO and 90% Aromatic solvent until a clear solution is formed, and adjusting to volume with Aromatic solvent .
  • Example C2 A wettable powder is formed from:
  • Active ingredient 50% w/w
  • a suspension concentrate is formed from: Active ingredient (Compound 1) 50% w/v Antifreeze (Propylene glycol) 5% w/v Ethoxylated tristyrylphenol phosphate
  • Attaclay (Attagel) 1.5% w/v
  • Antifoam (Rhodorsil AF426R) 0.003% w/v Water to 100 volumes by stirring the above ingredients together and milling in a bead mill.
  • a water dispersible granule is formed from: Active ingredient (Compound 1) 50% w/w Sodium dodecylbenzenesulphonate
  • Binder (Sodium lignosulphonate) 8% w/w China clay 30% w/w Microfine silicon dioxide (Tixosil 38)
  • Example C5 3% w/w by blending the above ingredients together, grinding the mixture in an air jet mill and granulating by addition of water in a suitable granulation plant (e.g. Fluid bed drier) and drying.
  • a suitable granulation plant e.g. Fluid bed drier
  • the active ingredient may be ground either on its own or admixed with some or all of the other ingredients.
  • a microemulsifiable concentrate is formed from:
  • Active Ingredient 10% w/w Gamma butyrolactone 20% w/w Isobutyl alcohol 10% w/w
  • the compounds of the invention have been used in herbicidal applications according to the following procedures.
  • the compounds of the invention were applied to the soil surface, containing the seeds, as described in (a) .
  • a single pot of the crop and each weed was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone. After treatment the pots were placed on capillary matting kept in a glass house, and watered overhead. Visual assessment of crop damage was made 20-24 days after spraying. The results were expressed as the percentage reduction in growth or damage to the crop or weeds, in comparison with the plants in the control pots.
  • Soya 2 2 leaves The compounds used to treat the plants were applied to the plants as described in (a) .
  • a single pot of each crop and weed species was allocated to each treatment, with unsprayed controls and controls sprayed with acetone alone .
  • Cyp Cyperus esculentus

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

Cette invention se rapporte à des 4-benzoylisoxazoles représentés par la formule (Ia) et à des 2-cyano-1,3-diones représentés par la formule (Ib) et à leur utilisation comme herbicides. Dans la formule (Ia), R représente hydrogène ou -CO2R1, R1 représente un groupe alkyle à chaîne droite ou ramifiée contenant 1 à 6 atomes de carbone et n = 0, 1 ou 2.
PCT/EP1998/003159 1997-05-15 1998-05-13 Procedes et derives herbicides Ceased WO1998051153A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU79164/98A AU7916498A (en) 1997-05-15 1998-05-13 Herbicidal methods and derivatives

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9709831.3 1997-05-15
GB9709829.7 1997-05-15
GBGB9709831.3A GB9709831D0 (en) 1997-05-15 1997-05-15 Chemical compounds
GBGB9709829.7A GB9709829D0 (en) 1997-05-16 1997-05-16 Chemical compositions

Publications (1)

Publication Number Publication Date
WO1998051153A1 true WO1998051153A1 (fr) 1998-11-19

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PCT/EP1998/003159 Ceased WO1998051153A1 (fr) 1997-05-15 1998-05-13 Procedes et derives herbicides

Country Status (3)

Country Link
AR (1) AR012697A1 (fr)
AU (1) AU7916498A (fr)
WO (1) WO1998051153A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999023886A1 (fr) * 1997-11-12 1999-05-20 Aventis Cropscience S.A. Procede permettant de freiner la progression des mauvaises herbes dans des cultures transgeniques
WO2000068204A1 (fr) * 1999-05-08 2000-11-16 Bayer Aktiengesellschaft Cetones de benzoyle substituees, leur procede de preparation et leur utilisation comme herbicides
EP2105437A1 (fr) * 2008-03-26 2009-09-30 Bayer CropScience Aktiengesellschaft 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles actifs en tant qu'herbicide

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487357A1 (fr) * 1990-11-22 1992-05-27 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles
EP0496631A1 (fr) * 1991-01-25 1992-07-29 Rhone-Poulenc Agriculture Ltd. Herbicides à base de 2-cyano-1,3-dione
EP0560482A1 (fr) * 1992-03-12 1993-09-15 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles et leur utilisation comme herbicides
EP0625508A2 (fr) * 1993-05-18 1994-11-23 Rhone Poulenc Agriculture Ltd. Dérivés de 2-cyano-1,3 dione contenant du soufre et leur emploi en tant qu'herbicides
WO1995022903A1 (fr) * 1994-02-25 1995-08-31 Rhone-Poulenc Agrochimie Nouveau procede pesticide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0487357A1 (fr) * 1990-11-22 1992-05-27 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles
EP0496631A1 (fr) * 1991-01-25 1992-07-29 Rhone-Poulenc Agriculture Ltd. Herbicides à base de 2-cyano-1,3-dione
EP0560482A1 (fr) * 1992-03-12 1993-09-15 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles et leur utilisation comme herbicides
EP0625508A2 (fr) * 1993-05-18 1994-11-23 Rhone Poulenc Agriculture Ltd. Dérivés de 2-cyano-1,3 dione contenant du soufre et leur emploi en tant qu'herbicides
WO1995022903A1 (fr) * 1994-02-25 1995-08-31 Rhone-Poulenc Agrochimie Nouveau procede pesticide

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999023886A1 (fr) * 1997-11-12 1999-05-20 Aventis Cropscience S.A. Procede permettant de freiner la progression des mauvaises herbes dans des cultures transgeniques
US6069115A (en) * 1997-11-12 2000-05-30 Rhone-Poulenc Agrochimie Method of controlling weeds in transgenic crops
WO2000068204A1 (fr) * 1999-05-08 2000-11-16 Bayer Aktiengesellschaft Cetones de benzoyle substituees, leur procede de preparation et leur utilisation comme herbicides
US6762152B1 (en) 1999-05-08 2004-07-13 Bayer Aktiengesellschaft Substituted benzoyl ketones, methods for producing them and their use as herbicides
EP2105437A1 (fr) * 2008-03-26 2009-09-30 Bayer CropScience Aktiengesellschaft 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles actifs en tant qu'herbicide
WO2009118125A1 (fr) * 2008-03-26 2009-10-01 Bayer Cropscience Ag 4- (3-aminobenzoyl) -5-cyclopropylisoxazoles à action herbicide
US8188009B2 (en) 2008-03-26 2012-05-29 Bayer Cropscience Ag 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles effective as herbicides

Also Published As

Publication number Publication date
AR012697A1 (es) 2000-11-08
AU7916498A (en) 1998-12-08

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