WO2000035916A1 - 4-benzoylisoxazoles herbicides - Google Patents

4-benzoylisoxazoles herbicides Download PDF

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Publication number
WO2000035916A1
WO2000035916A1 PCT/EP1999/010455 EP9910455W WO0035916A1 WO 2000035916 A1 WO2000035916 A1 WO 2000035916A1 EP 9910455 W EP9910455 W EP 9910455W WO 0035916 A1 WO0035916 A1 WO 0035916A1
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substituted
formula
halogen
carbon atoms
unsubstituted
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PCT/EP1999/010455
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Mary Susan Cramp
David William Hawkins
Neil Jonathan Geach
Christopher J. Pearson
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Aventis Cropscience S.A.
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Priority to AU22868/00A priority Critical patent/AU2286800A/en
Publication of WO2000035916A1 publication Critical patent/WO2000035916A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings

Definitions

  • This invention relates to novel 4-benzoylisoxazole derivatives, compositions containing them, processes for their preparation, intermediates in their preparation and their use as herbicides.
  • Herbicidal 4-benzoylisoxazoles are described in a number of patent publications for example European Patent Publication Numbers 0418175, 0487357, 0527036, 0527037, 0560482 and 0560483. However none of the above publications disclose or suggest the presence of an aromatic heterocyclic ring linked by a ring nitrogen atom to the benzoyl ring.
  • the present invention provides 4-benzoylisoxazole derivatives of formula (I):
  • R represents :- lower alkyl, lower haloalkyl; or phenyl substituted or unsubstituted by halogen , lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, nitro, carboxy, lower alkoxycarbonyl or -S(O)pR4;
  • Ri represents:- lower alkyl or lower haloalkyl; or a cycioalkyl group containing from three to six carbon atoms substituted or unsubstituted by one or more Rl2 groups or one or more halogen atoms;
  • R2 represents :- halogen; lower alkyl which is substituted by one or more groups -OR 5 ; a cycioalkyl group containing from three to six carbon atoms; or a group selected from nitro, cyano, -CO2R 5 , -NR 5 R 6 , -S(O) p R 7 ,
  • R3 represents a 5-membered heteroaromatic ring of formula (II):
  • D, E, G and J independently represent CR*4 or a nitrogen atom, with at least one of D, E, G and J representing CR ⁇ 4 (when more than one R*4 group is present they may be the same or different);
  • Rl4 represents a group selected from hydrogen, halogen, R* 7 , nitro, cyano, -CO 2 R 5 , -S(O) p R! 6 , -OR 16 , -NR 5 R 6 and cyclopropyl; or two adjacent groups CRl4 may form a phenyl or 5- to 7- membered heteroaromatic ring which is fused to the first ring and is unsubstituted or substituted by one or more groups R 15 ; and when present the 5- to 7- membered heterocyclic ring contains from one to four heteroatoms in the ring which may be the same or different selected from nitrogen, oxygen and sulphur; x represents one or two, when x represents two the R ⁇ groups may be the same or different;
  • R4 represents lower alkyl or lower haloalkyl
  • R 5 and R" which may be the same or different, each represents hydrogen or R*2;
  • R 7 represents :-
  • R!2 or a cycioalkyl group containing from three to six carbon atoms; or a group -(CH 2 ) W - [phenyl unsubstituted or substituted by one or more groups Rl3 which may be the same or different]; w represents zero or one;
  • R represents:- hydrogen, R 7 , or ORl6;
  • R9 and R l O independently represent hydrogen, lower alkyl or lower haloalkyl (preferably containing up to three carbon atoms);
  • Rl2 represents :- lower alkyl, lower haloalkyl, lower alkenyl, lower haloalkenyl, lower alkynyl or lower haloalkynyl;
  • Rl3 represents a group selected from halogen, R ⁇ 7 , nitro, cyano, -CO 2 R 5 , -S(O) p R 16 , -OR 16 and -NR 5 R 6 ;
  • Ri 5 represents halogen, or R l 2 ;
  • Rl6 represents lower alkyl or lower haloalkyl
  • Ri 7 represents a straight- or branched- chain alkyl group containing one to three carbon atoms unsubstituted or substituted by one or more halogen atoms;
  • Y is oxygen or sulphur (preferably Y represents oxygen);
  • Z represents a group selected from R ⁇ 5 -NR1 °R19 3 -SR 7 and -OR 7 ;
  • Rl8 and R ⁇ independently represent hydrogen or R 7 ; and agriculturally acceptable salts thereof, which possess valuable herbicidal properties.
  • substituents R, Ri to R ⁇ and Z may contribute to optical isomerism and/or stereoisomerism. All such forms and isomers thereof, and mixtures thereof are embraced by the present invention.
  • 'lower haloalkyl' means a straight- or branched- chain alkyl group having one to six carbon atoms, substituted by one or more halogens;
  • 'lower alkoxy' means a straight- or branched- chain alkoxy group having one to six carbon atoms;
  • 'lower haloalkoxy means a straight- or branched- chain alkoxy group having one to six carbon atoms, substituted by one or more halogens;
  • 'lower alkenyl' means a straight- or branched- chain alkenyl group having two to six carbon atoms;
  • 'lower haloalkenyl' means a straight- or branched- chain alkenyl group having two to six carbon atoms, substituted by one or more halogens;
  • 'lower alkynyl' means a straight- or branched- chain alkynyl group having three to six carbon atoms;
  • 'lower haloalkynyl' means a straight- or branched- chain alkynyl group having three to six carbon atoms, substituted by one or more halogens; 'halogen' means a fluorine, chlorine, bromine or iodine atom.
  • agriculturally acceptable salts salts the cations or anions 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.
  • Suitable acid addition salts formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates and nitrates and salts with organic acids, for example acetic acid.
  • the compounds of the invention in certain aspects of their properties show advantageous properties over known compounds.
  • Compounds in which one R-> group is present are preferred (preferably the R ⁇ group is at the 2- or 4- position on phenyl).
  • R ⁇ is selected from pyrazol-1-yl, imidazol-1-yl, 1,2,4-triazol-l-yl, 1,2,3-triazol-l-yl, l,2,3-triazol-2-yl and 1,2,3,4-tetrazol-l-yl, unsubstituted or substituted by halogen or R 7 .
  • R represents lower alkyl or lower haloalkyl.
  • Rl represents cyclopropyl or 1 -methylcyclopropyl (cyclopropyl is especially preferred).
  • R 2 represents halogen, a straight- or branched- chain alkyl group containing up to four carbon atoms unsubstituted or substituted by one or more halogen atoms; a group selected from nitro, cyano, -S(O) p R 7 , -OR 7 and -CH 2 S(O)qR 7 wherein R 7 represents lower alkyl or lower haloalkyl; or benzyl unsubstituted or substituted by -S(O)pRl6 wherein R " represents lower alkyl; or two groups R 2 together with adjacent carbon atoms of the phenyl ring form a second phenyl ring.
  • n one or two.
  • N preferred class of compounds of formula (I) above are those wherein: - Ri represents cyclopropyl or 1 -methylcyclopropyl;
  • R2 represents :- a straight- or branched- chain alkyl group containing up to four carbon atoms unsubstituted or substituted by one or more halogen atoms; or a group selected from halogen, nitro, -S(O) p R 7 , -OR 7 ,
  • R3 represents a 5-membered heteroaromatic ring of formula (II) which is selected from pyrazol-1-yl, imidazol-1-yl, 1 ,2,4-triazol-l-yl, 1,2,3-triazol-l-yl, l,2,3-triazol-2-yl and 1 ,2,3,4-tetrazol-l-yl, , which are substituted by one or two groups R ⁇ ; R 7 and R 8 independently represent lower alkyl or lower haloalkyl;
  • R 1 1 represents -SO 2 R 7 or CO 2 R 7 ;
  • Rl4 represents hydrogen, halogen, a straight- or branched- chain alkyl group containing up to three carbon atoms unsubstituted or substituted by one or more halogen atoms; or -S(O) p Rl ⁇ , NO 2 or
  • R represents lower alkyl or lower haloalkyl
  • Ri represents cyclopropyl
  • R2 represents:- halogen; a straight- or branched- chain alkyl group containing up to four carbon atoms unsubstituted or substituted by one or more halogen atoms; or a group selected from -S(O) p R 7 , -CH 2 S(O)qR 7 and -
  • R represents a pyrazol-1-yl, imidazol-1-yl, 1,2,3-triazol-l-yl, l,2,3-triazol-2-yl, 1,2,4-triazol-l-yl or 1,2,3,4-tetrazol-l-yl ring substituted by one or two R*4 groups, wherein R 4 represents hydrogen, optionally halogenated methyl or -S(O) p Rl6; R 7 and Rl° " represent methyl or ethyl; and n represents 0, 1 or 2.
  • a further particularly preferred class of compounds of formula (I) above are those wherein: -
  • R represents a straight- or branched chain alkyl group containing from one to three carbon atoms
  • Ri represents cyclopropyl
  • R2 represents :- halogen, methyl, halogenated methyl, -S(O) p CH3 or OCH3;
  • R3 represents imidazol-1-yl, 1,2,3-triazol-l-yl, l,2,3-triazol-2-yl or 1,2,4-triazol-l-yl, unsubstituted or substituted on the ring carbon atoms by one or two methyl groups; and n represents one or two.
  • Particularly important compounds of the invention include: 5 -cyclopropyl-4- [4-( 1 ,2,4-triazol- 1 -yl)-2-trifluoromethylbenzoyl] - 3-(methylthio)isoxazole (Compound 1);
  • Me means methyl
  • Et means ethyl
  • Bu means butyl.
  • subscripts do not appear in the Table it will be understood that in appropriate cases they are present (e.g. CF3 means CF3 etc.).
  • R, R 1 , R R3 ; X? n and r are as defined above and 7?- represents a leaving group for example halogen (preferably fluoro), with a compound of formula R ⁇ -H.
  • the reaction is generally performed in the presence of a base, for example sodium hydride or caesium carbonate, in an inert solvent, for example N,N-dimethylformamide at a temperature from 0°C to 100°C.
  • the reaction is generally performed in the presence of a base and a solvent such as acetonitrile, N,N-dimethylformamide or dimethylsulphoxide .
  • Suitable bases for the reaction include alkali metal carbonates or hydrides such as potassium carbonate or sodium hydride; or trialkylamines such as triethylamine; or a mixture of potassium fluoride and alumina, according to procedures described by Villemin et. al. in Synthesis 301 (1991); Pak et. al. in Synthesis 793 (1988) and Augustin et. al. in Tetrahedron 32, 3055 (1976).
  • Compounds of formula (III) wherein R represents optionally substituted phenyl may be prepared by the transketalisation reaction of the corresponding compound of formula (III) wherein R represents lower alkyl or lower haloalkyl using an optionally substituted thiophenol in a solvent such as ethanol, tetrahydrofuran or N,N- dimethylformamide at a temperature of from 20°C to the reflux temperature of the solvent.
  • Compounds of formula (V) may be prepared by the reaction of an acid chloride of formula (VII):
  • 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 (VII) may be prepared by the reaction of a benzoic acid of formula (XII):
  • a chlorinating agent for example thionyl chloride at the reflux temperature of the mixture.
  • benzoyl chlorides may also be prepared by reaction of the benzoic acid with oxalyl chloride in a solvent such as 1 ,2-dichloroethane at from ambient to reflux temperature.
  • Esters of formula (X) may be prepared from acids of formula (XII) according to known methods.
  • Benzoic acids of formula (XII) or esters of formula (X) in which R2, R , R20 5 X and n are as defined above may be prepared by the reaction of the corresponding compound of formula (XII) or (X) in which R is replaced by !? ⁇ (Z ⁇ is as defined above preferably fluorine), with a compound of formula R3-H using the same procedure as described above for the preparation of compounds of formula (I) from compounds of formula (IV).
  • compounds in which p, q or r is one or two may be prepared by the oxidation of the sulphur atom of the corresponding compounds in which p, q or r is 0 or
  • 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.
  • Triethylamine (15.8ml) then carbon disulphide (3.7ml) were added to a solution of 3-cyclopropyl-l-(4-fluoro-2-methylphenyl)propan-l,3- dione (11.4g) in N,N-dimethylformarnide and stirred for 1.5 hours.
  • a solution of methyl iodide (7.1ml) in N,N-dimethylformamide was added and stirred for 2 days at 20°C. The mixture was added to water,
  • the isoxazole derivative is 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,
  • 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. In general, taking these factors into account, application rates from 0.01kg to 2kg of active material per hectare give good results.
  • the compounds of formula (I) may be used to control selectively the growth of weeds, for example to control the growth of those species hereinbefore mentioned, by pre- or post-emergence application in a directional or non-directional fashion, e.g. by directional or non-directional spraying, to a locus of weed infestation which is an area used, or to be used, for growing crops, for example cereals, e.g. wheat, barley, oats, maize and rice, soya beans, field and dwarf beans, peas, lucerne, cotton, peanuts, flax, onions, carrots, cabbage, oilseed rape, sunflower, sugar beet, and permanent or sown grassland before or after sowing of the crop or before or after emergence of the crop.
  • application rates from 0.01kg to 1.0kg, and preferably from 0.01kg to 1.0kg, and preferably from 0.01kg to 1.0kg, and preferably from 0.01kg to 1.0kg, and preferably from 0.01kg to 1.0kg, and
  • the compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, by pre- or post- emergence application in established orchards and other tree-growing areas, for example forests, woods and parks, and plantations, e.g. sugar cane, oil palm and rubber plantations.
  • plantations e.g. sugar cane, oil palm and rubber plantations.
  • they may be applied in a directional or non- directional fashion (e.g. by directional or non-directional spraying) to the weeds or to the soil in which they are expected to appear, before or after planting of the trees or plantations at application rates from 0.25kg to 2.0kg, and preferably from 0.25kg to 1.0kg of active material per hectare.
  • the compounds of formula (I) may also be used to control the growth of weeds, especially those indicated above, at loci which are not crop-growing areas but in which the control of weeds is nevertheless desirable.
  • non-crop-growing areas include airfields, industrial sites, railways, roadside verges, the verges of rivers, irrigation and other waterways, scrublands and fallow or uncultivated land, in particular where it is desired to control the growth of weeds in order to reduce fire risks.
  • the active compounds When used for such purposes in which a total herbicidal effect is frequently desired, the active compounds are normally applied at dosage rates higher than those used in crop-growing areas as hereinbefore described. The precise dosage will depend upon the nature of the vegetation treated and the effect sought.
  • 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.
  • compositions suitable for herbicidal use comprising one or more of the isoxazole derivatives of formula (I) or agriculturally acceptable salts thereof, 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)].
  • compositions in which the compounds of formula (I) are dissolved in other components.
  • herbicide 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 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, spreading agents, stabilisers, sequestering agents, anti-caking agents, colouring agents and corrosion inhibitors. These adjuvants may also serve as carriers or diluents.
  • Herbicidal compositions according to the present invention may also comprise the compounds 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.
  • synthetic pyrethroids e.g permethrin and cypermethrin
  • fungicides e.g. carbamates, e.g. methyl N-(l-butyl-carbamoyl- benzimidazol-2-yl)carbamate, and triazoles e.g. l-(4-chloro-phenoxy)- 3,3-dimethyl-l-(l,2,4-triazol-l-yl)-butan-2-one.
  • 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 utilised in the form of conventional derivatives, for example alkali metal and amine salts and esters.
  • the following Examples illustrate herbicidal compositions according to the present invention. The following trade marks appear in the Examples: Synperonic, Solvesso, Arylan, Arkopon, Sopropon, Tixosil, Soprophor, Attagel, Rhodorsil.
  • An emulsif ⁇ able concentrate is formed from: Active ingredient (Compound 1) 20% w/v
  • NMP N-Methylpyrrolidinone 25% w/v Calcium dodecylbenzenesulphonate 70%
  • Nonylphenol ethylene oxide propylene oxide condensate (Synperonic NPE 1800) 6% w/v Aromatic solvent (Solvesso) to 100 volumes by stirring NMP, active ingredient (Compound 1), CaDDBS,
  • Example C2 A wettable powder is formed from:
  • Active ingredient 50% w/w
  • a suspension concentrate is formed from:
  • 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
  • Binder (Sodium lignosulphonate) 8% w/w
  • Microfme silicon dioxide (Tixosil 38) 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.
  • the compounds of the invention have been used in herbicidal applications according to the following procedures.
  • Seeds of various broad-leaf and grass weed and crop species were sown, and herbicide dissolved in a mixture of acetone and water was applied at a rate of 250g/ha to the soil surface.
  • the said weeds were Amaranthus retroflexus, Abutilon theophrasti. Ipomoea purpurea. Galium aparine. Setaria viridis. Alopecurus myosuroides, Avena fatua and Echinochloa crus-galli.
  • the crop species used were Soya, Maize, Rice and Wheat.
  • Compounds 1-5 of the invention gave at least 80% reduction in growth of one or more weed species in the above Test Methods A or B.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés correspondant à la formule (1), dans laquelle R3 représente un noyau aromatique à 5 éléments correspondant à la formule (2), dans laquelle D, E, G et J représentent indépendamment CR14 ou un atome d'azote, au moins un des D, E, G et J représentant CR14, ainsi que leur utilisation en tant qu'herbicides.
PCT/EP1999/010455 1998-12-15 1999-12-14 4-benzoylisoxazoles herbicides WO2000035916A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22868/00A AU2286800A (en) 1998-12-15 1999-12-14 Herbicidal 4-benzoylisoxazoles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB9827617.3A GB9827617D0 (en) 1998-12-15 1998-12-15 New herbicides
GB9827617.3 1998-12-15

Publications (1)

Publication Number Publication Date
WO2000035916A1 true WO2000035916A1 (fr) 2000-06-22

Family

ID=10844271

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/010455 WO2000035916A1 (fr) 1998-12-15 1999-12-14 4-benzoylisoxazoles herbicides

Country Status (3)

Country Link
AU (1) AU2286800A (fr)
GB (1) GB9827617D0 (fr)
WO (1) WO2000035916A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997043270A1 (fr) * 1996-05-14 1997-11-20 Novartis Ag Derives d'isoxazole et leur utilisation comme desherbants
WO1998042678A1 (fr) * 1997-03-24 1998-10-01 Dow Agrosciences Llc Composes 1-alkyl-4-benzoyl-5-hydroxypyrazole et leur utilisation comme herbicides
US5834402A (en) * 1995-02-24 1998-11-10 Basf Aktiengesellschaft Isoxazolylbenzoyl derivatives
WO1999003856A1 (fr) * 1997-07-18 1999-01-28 Rhone-Poulenc Agriculture Limited Derives de 4-benzoyl-isoxazole- et de 4-benzoyl-pyrazole et derives de 2-cyano 1,3-dione utilises comme herbicides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5834402A (en) * 1995-02-24 1998-11-10 Basf Aktiengesellschaft Isoxazolylbenzoyl derivatives
WO1997043270A1 (fr) * 1996-05-14 1997-11-20 Novartis Ag Derives d'isoxazole et leur utilisation comme desherbants
WO1998042678A1 (fr) * 1997-03-24 1998-10-01 Dow Agrosciences Llc Composes 1-alkyl-4-benzoyl-5-hydroxypyrazole et leur utilisation comme herbicides
WO1999003856A1 (fr) * 1997-07-18 1999-01-28 Rhone-Poulenc Agriculture Limited Derives de 4-benzoyl-isoxazole- et de 4-benzoyl-pyrazole et derives de 2-cyano 1,3-dione utilises comme herbicides

Also Published As

Publication number Publication date
GB9827617D0 (en) 1999-02-10
AU2286800A (en) 2000-07-03

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