WO1995022903A1 - Nouveau procede pesticide - Google Patents

Nouveau procede pesticide Download PDF

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Publication number
WO1995022903A1
WO1995022903A1 PCT/EP1995/000616 EP9500616W WO9522903A1 WO 1995022903 A1 WO1995022903 A1 WO 1995022903A1 EP 9500616 W EP9500616 W EP 9500616W WO 9522903 A1 WO9522903 A1 WO 9522903A1
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
branched
straight
chain alkyl
isoxazole
Prior art date
Application number
PCT/EP1995/000616
Other languages
English (en)
Inventor
Paul Alfred Cain
David Chou
Nancy D. Herman
Daniel B. Gant
Original Assignee
Rhone-Poulenc Agrochimie
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
Application filed by Rhone-Poulenc Agrochimie filed Critical Rhone-Poulenc Agrochimie
Priority to AU17584/95A priority Critical patent/AU1758495A/en
Publication of WO1995022903A1 publication Critical patent/WO1995022903A1/fr

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl 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
    • 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

Definitions

  • This invention relates to 4-substituted isoxazole derivatives, compositions containing them and their use against arthropod, plant nematode, helminth and protozoan pests, or as intermediates in the synthesis of such pesticidally active compounds.
  • A is C(0) and B is R 1 ; or A is C(O)R! and B is W; and in which R is hydrogen or -CO2R6;
  • R 1 is:- straight- or branched- chain alkyl group having up to six carbon atoms; cycloalkyl group having from three to six carbon atoms, optionally having a methyl group at its 1-position; or phenyl optionally having from one to three substituents which may be the same or different selected from the group consisting of halogen; a straight- or branched- chain alkyl, or alkoxy group having up to three carbon atoms, optionally substituted by one or more halogen atoms; or cyano;
  • W represents: phenyl having a group R 2 in its 2-position; R ⁇ in its 3-position; R4 in its 4-position; and R ⁇ in its 5-position;
  • R 2 is:- hydrogen or halogen; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more halogen; straight- or branched- chain alkyl up to four carbon atoms, substituted by -OR 7 ; a member selected from the group consisting of nitro, cyano,
  • R 3 is:- hydrogen or halogen; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more halogen; straight- or branched- chain alkyl having up to four carbon atoms, substituted by -OR 7 ; straight- or branched- chain alkenyl having up to four carbon atoms; or a member selected from the group consisting of cyano, -OR 10, -S(O) m R 8 . -OSO2R 8 , -CO 2 R 9 and -O(CH 2 ) p OR 7 -N(R )(R 12 );
  • R 4 is:- hydrogen or halogen; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more halogen; straight- or branched- chain alkyl up to four carbon atoms, substituted by -OR 7 ; or a member selected from the group consisting of nitro, cyano, -S(O) m R 8 , -OSO2R 8 -CO 2 R 9 , -OR 10, -O(CH 2 ) p OR 7 and
  • R 2 , R 3 and R 4 is selected from
  • R5 is:- hydrogen or hale n; or straight- or branched- chain alkyl or alkoxy having up to four carbon atoms;
  • R6 is straight- or branched- chain alkyl, alkenyl or alkynyl having up to six carbon atoms, optionally substituted by one or more halogen;
  • R 7 is straight- or branched- chain alkyl having up to six carbon atoms
  • R 8 and R 9 independently are straight- or branched- chain alkyl having up to three carbon atoms;
  • RlO is phenyl, optionally bearing from one to three substituents which may be the same or different selected from the group consisting of halogen, a straight- or branched- chain alkyl, alkoxy group having up to three carbon atoms, optionally substituted by one or more halogen, and cyano;
  • R11 and R* 2 are independently selected from R ⁇ RlO, -C(O)R6 -C(O)R 10 , -CO 2 R 6 and -C(O)NHR6 n and m independently are zero, one or two; and p is an integer from one to four; with the proviso that when R 4 is -S(O) m R 8 , R 3 is not -0(CH 2 ) p OR 7
  • the groups A, B and R to R ⁇ 2 may give rise to geometric and/or optical isomers. All such forms are embraced by the present invention. It will be understood that where provisos appear in the description they are present for reasons of biological efficacy.
  • a preferred class of compounds of formula (I) are those wherein:
  • R 1 is:- straight- or branched- chain alkyl having up to three carbon atoms; or cycloalkyl having from three or four carbon atoms, optionally having a methyl at its 1-position;
  • R 2 is:- hydrogen, fluorine, chlorine or bromine; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more halogen; a member selected from the group consisting of nitro, cyano, -S(O) m R 8 , -OSO2R 8 and -CO 2 R 9 ;
  • R3 is:- hydrogen, fluorine, chlorine or bromine; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more chlorine or fluorine; straight- or branched- chain alkyl having up to four carbon atoms substituted by -OR 7 ; straight- or branched- chain alkenyl having up to four carbon atoms; or a member selected from the group consisting of cyano, -S(O) m R 8 , -OSO2R 8 , -OR 10 , -CO 2 R 9 and -O(CH 2 ) p OR 7 ;
  • R 4 is:- hydrogen, fluorine, chlorine or bromine; straight- or branched- chain alkyl or alkoxy having up to four carbon atoms, optionally substituted by one or more halogen; or nitro;
  • R5 is hydrogen
  • R6 is straight- or branched- chain alkyl having up to four carbon atoms
  • R 7 is straight- or branched- chain alkyl having up to four carbon atoms
  • R 9 is a straight- or branched- chain alkyl group having up to three carbon atoms
  • RlO is phenyl, optionally bearing from one to three substituents which may be the same or different selected from the group consisting of fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy.
  • a further preferred class of compounds of formula (I) are those wherein: Rl is:- straight- or branched- chain alkyl group having up o three carbon atoms;or a cyclopropyl group;
  • R 2 is:- hydrogen, fluorine, chlorine or bromine; straight- or branched- chain alkyl or alkoxy having one or two carbon atoms, optionally substituted by one or more halogen; a member selected from the group consisting of nitro, cyano -OR , -SR!0, and -CO 2 R 9 ;
  • R 3 is:- hydrogen, fluorine, chlorine or bromine; a straight- or branched- chain alkyl or alkoxy group having one or two carbon atoms, optionally substituted by one or more chlorine or fluorine atoms; methoxymethyl; straight- or branched- chain alkenyl having up to four carbon atoms; or a member selected from the group consisting of cyano, -OR 10 , -CO2R 9 and -OCH 2 CH 2 OCH 3 ;
  • R 4 is:- hydrogen, fluorine, chlorine or bromine; straight- or branched- chain alkyl or alkoxy having one or two carbon atoms, optionally substituted by one or more halogen;
  • R5 is hydrogen
  • R6 is straight- or branched- chain alkyl having up to four carbon atoms
  • R 9 is methyl or ethyl
  • RlO is phenyl, optionally bearing from one to three substituents which may be the same or different selected from the group consisting of fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy.
  • substituents which may be the same or different selected from the group consisting of fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and trifluoromethoxy.
  • R* and W are as defined above and X represents alkoxy- ( ⁇ .g. ethoxy) or N,N-dialkylamino (e.g. N,N-dimethylamino), with fo-droxylamine or a salt thereof (such as hydroxylamine hydrochloride).
  • the reaction is generally carried out in a solvent such as ethanol or aceto ⁇ itrile, optionally in the presence of a base or acid acceptor such as triethylamine or sodium acetate.
  • reaction is generally performed for example using a mixture prepared from chromium trioxide and aqueous sulphuric acid.
  • a method ⁇ o£ control of pests at a locus which comprises the treatment of the ICBKE ⁇ S (e.g., by application or administration) with an effective amoum: of a compound of formula I, wherein the substituent groups are as hereinbefore defined.
  • the locus includes, for example, the pest itself or the place (plant, animal, person, field, structure, premises, forest, orchard, waterway, soil, plant or animal product, or the like) where the pest resides or feeds.
  • the compounds of this inven ; n are useful in the control via foliar application or systemic action of some arthropods, especially some insects, which feed on the above ground portions of plants.
  • Control of foliar pests may additionally be provided by application to the plant roots or plant seeds with subsequent systemic translocation to the above ground portions of the plants.
  • the compounds of this invention may be useful to control soil insects, such as com rootworm, termites (especially for protection of structures), root maggots, wireworms, root weevils, stalkborers, cutworms, root aphids, or grubs. They may also be used to provide activity against plant pathogenic nematodes, such as root-knot, cyst, dagger, lesion, or stem or bulb nematodes, or against mites.
  • the compounds are advantageously applied to or incorporated at an effective rate into the soil in which crops are planted or to be planted or to the seeds or growing plant roots.
  • the compounds are especially useful in the control of many insects, especially filth flies or other
  • Dipteran pests such as houseflies, stableflies, soldierflies, hornflies, deerflies, horseflies, midges, punkies, blackflies, or mosquitoes.
  • Compounds of the invention may be used in the following applications and on the following pests including arthropods, especially insects or mites, nematodes, or helminth or protozoan pests:
  • the invention provides methods of control of pests via application or administration of an effective amount of compounds of formula I at a locus which comprises treatment of the locus.
  • a method for example, comprises applying to the plants or to the medium in which they grow an effective amount of a compound of the invention.
  • the active compound is generally applied to the locus in which the arthropod or nematode infestation is to be controlled at an effective rate in the range of about 0.005 kg to about 15 kg of the active compound per hectare of locus treated.
  • a lower rate may offer adequate protection.
  • adverse weather conditions, resistance of the pest or other factors may require that the active ingredient be used at higher rates.
  • an effective rate range of the active compound is from about 0.01 kg/ha to about 2 kg/ha.
  • the active compound When a pest is soil-borne, the active compound generally in a formulated composition, is distributed evenly over the area to be treated (i.e., for example broadcast or band treatment) in any convenient manner. Application may be made, if desired, to the field or crop-growing area generally or in close proximity to the seed or plant to be protected from attack.
  • the active component can be washed into the soil by spraying with water over the area or can be left to the natural action of rainfall.
  • the formulated compound can, if desired, be distributed mechanically in the soil, for example by ploughing, disking, or use of drag chains. Application can be prior to planting, at planting, after planting but before sprouting has taken place, or after sprouting.
  • a method of control may also comprise treatment of the seed prior to planting with subsequent control effected after planting the seed.
  • Methods of control of pests also consist of application to or treatment of the foliage of plants to control arthropods, especially insects or mites, or nematodes attacking the aerial parts of the plants.
  • methods of control of pests by the invention compounds are provided to control pests which feed on parts of the plant remote from the point of application, e.g., leaf feeding insects which are controlled via systemic action ⁇ s£ the active compound when applied for example to the roots of a pi at or to the plant seed prior to planting
  • the comjj crizds of the invention may reduce attacks on a plant by means of ⁇ ntifeeding or repellent effects.
  • the compounds of the invention and methods of control of pests therewith are of particular value in the protection of field, forage, plantation, glasshouse, orchard or vineyard crops, of ornamentals, or of plantation or forest trees, for example: cereals (such as maize, wheat, rice, or sorghum), cotton, tobacco, vegetables
  • plants such as beans, cole crops, curcurbits, lettuce, onions, tomatoes or peppers
  • field crops such as potatoes, sugar beets, ground nuts, soybeans, or oil seed rape
  • sugar cane grassland or forage crops (such as maize, sorghum, or lucerne)
  • plantations such as tea, coffee, cocoa, banana, palm oil, coconut, rubber, or spices
  • chards or groves such as of stone or pit fruit, citrus, kiwifruit, avocado, mango, olives or walnuts
  • vineyards ornamental plants, flowers or vegetables or shrubs under glass or in gardens or parks, or forest trees (both deciduous and evergreen) in forests, plantations or nurseries.
  • stored products such as grains, fruits, nuts, spices or tobacco, whether whole, milled or compounded into products, from moth, beetle, mite or grain weevil attack.
  • stored animal products such as skins, hair, wool or feathers in natural or converted form (e.g. as carpets or textiles) from moth or beetle attack as well as stored meat, fish or grains from beetle, mite or fly attack.
  • the compounds of the invention and methods of use thereof are of particular value in the control of arthropods, helminths or protozoa which are injurious to, or spread or act as vectors of diseases in man and domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges, or biting, nuisance or myiasis flies.
  • the compounds of the invention are particularly useful in controlling arthropods, helminths or protozoa whf n are present inside domestic host animals or which feed in or c_m the skin or suck the blood of the animal, for which purpose tht may be administered orally, parenterally, percutaneously or topically.
  • test compounds were formulated for use according to the following methods.
  • a solution or suspension was prepared by adding the test compound to a solution of dimethylformamide, acetone, emulsifiers which are alkyla ⁇ jfH polyether alcohols organic sulfonates, and water.
  • the result was a 500 ppm concentration of test compound.
  • the water-acetone-DMF-emulsifer solution containing test compound was adjusted with a 20% by weight aqueous solution of sucrose to provide a 250 or 500 ppm concentration of the test compound.
  • the water-acetone-DMF-emulsifer solution containing test compound was adjusted for a treatment rate of 10.0 ppm soil concentration.
  • test compound For southern com rootworm and black cutworm tests, the water-acetone-DMF-emulsifer solution containing test compound was adjusted for a treatment rate of 6.75 ppm.
  • the water-acetone- DMF-emulsifer solution containing test compound was adjusted for a treatment rate of 21 or 23 kg/ha soil concentration.
  • test compounds were then evaluated for their pesticidal activity at specified concentrations, in ppm (parts per million) by weight or in kg/ha (kilograms per hectare). The following procedures were used to evaluate a number of compounds within the scope of the invention.
  • Twospotted spider mite A sufficient number of two-spotted spider mites (150-200) for testing were transferred to the fresh bean leaves within a period of twenty-four hours. The infested leaves were wet to runoff with the 500 ppm test compound formulation. As an untreated control, the water-acetone-DMF-emulsif ⁇ aar solution containing no test compound was also applied west, to runoff to infested leaves . The treated leaves were held for three or six days, after which a mortality count of motile forms was made.
  • Twospotted spider mite Females were allowed to oviposit on bean plants for a period of about 24 hours, after which the leaves of the plant were dipped into a solution of TEPP (tetraethyl pyrophosphate) in order to kill the motile forms and prevent additional egg laying. This dipping procedure did not affect the viability of the eggs.
  • the infested leaves were wet to runoff with the 500 ppm test compound formulation.
  • a water-acetone-DMF-emulsifier solution containing no test compound was also wet to runoff on infested leaves. The treated leaves were held for seven days, after which a mortality count of egg forms was made along with notations on residual activity on hatched larvae.
  • Buckthorn or cotton aphid Adult and nymphal stages of buckthorn or cotton aphid were reared on potted dwarf nasturtium or cotton plants, respectively. Plants infested with 100-150 aphids were wet to runoff with the 500 ppm test compound formulation. As an untreated control, a water-acetone-DMF-emulsifier solution containing no test compound was also applied wet to runoff to infested plants. The treated plants were stored for one day for buckthorn aphid and three days for cotton aphid, after which the dead aphids were counted.
  • Cotton aphid - systemic test Cotton seeds were placed on top of the soil surface in pots containing moist soil. The test compound solution was applied as a drench to the top of the soil and seeds for a treatment rate equilvalent to 10.0 ppm soil concentration. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. The soil surface and seeds were covered with moist soil. The pots were held in the greenhouse for the duration of the bioassay. When the cotyledons of the cotton were expanded (approximately 7 days after planting), the cotton was infested with approximately 25 cotton aphids (mixed population). The plants were rated for aphid control three and six days after infestation.
  • Southern arm worm, Mexican bean beetle Bean leaves were wet to noff with the 500 ppm test compound formulation.
  • a water-acetone-DMF-emulsifier solution containing no test compound was also applied wet to mnoff to bean leaves.
  • Five or six randomly selected second instar southern armyworm larvae or Mexican bean beetle larvae were introduced into each plastic container with the dry treated leaves. The container was closed and held for five days. Larvae which were unable to move the length of the body, even upon stimulation by prodding, were considered dead.
  • House fly Four to six day old adult house flies were used. The flies were immobilized by anesthetizing with carbon dioxide. A bait cup was prepared which contained the 250 or 500 ppm test compound formulation / sucrose solution and one or two absorbent cotton pad(s). As an untreated control, a water-acetone-DMF- emulsifier-sucrose solution containing no test compound was applied in a similar manner. The bait cup was introduced inside the cage prior to admitting 12 - 25 anesthetized flies. Mortality was assessed after 24 hours. Following the above test procedure, compounds 53, 54, 143,
  • Southern root-knot nematode Eggs and second stage juveniles (J2s) of southern root-knot nematodes were obtained from infected roots of reared tomato plants. Pots containing moist soil were treated with the test compound solution for a treatment rate of
  • roots of the tomato or cotton seedling were evaluated for galling on a rating scale from 1 to 5 with one equal to severe galling, relative to untreated control, and five to no galling, i.e., complete control.
  • Southern corn rootworm Black cutworm: Corn seeds were placed in a glass jar and covered with dry sandy loam soil. The 500 ppm test compound was applied for a soil concentration of 6.75 ppm. As an untreated control, an aliquot of a water-acetone-DMF- emulsifier solution containing no test compound was applied in a similar manner. After incubating covered for 24 hours, the soil was mixed and inoculated with approximately 25 southern corn rootworm eggs. Following an additional 48 hours, two late second to early third instar black cutworms were placed in the jar with a portion of insect diet. Eight days after infestation, mortality was assessed visually for cutworm and by Berlese funnel extraction for rootworm.
  • Black cutworm - systemic test Com seeds were placed on top of the soil surface in pots containing moist soil. The test compound solution was applied as a drench to the top of the soil and seeds for a treatment rate equilvalent to 10.0 ppm soil concentration. As an untreated control, an aliquot of a water-acetone-DMF-emulsifier solution containing no test compound was applied in a similar manner. The soil surface and seeds were covered with moist soil. The pots were held in the greenhouse for the duration of the bioassay. Ten days after treatment, the corn seedling was clipped and placed in a plastic cup with 2 late second to early third instar black cutworm larvae. Mortality was assessed visually 4 days after infestation. Following the above test procedure, compounds 173, 177-180,

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  • 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)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Procédé de lutte contre les parasites dans un certain lieu, consistant à traiter ce lieu avec un composé efficace de la formule (I) dans laquelle R, A et B sont tels que définis dans la description.
PCT/EP1995/000616 1994-02-25 1995-02-21 Nouveau procede pesticide WO1995022903A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU17584/95A AU1758495A (en) 1994-02-25 1995-02-21 New pesticidal method

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US20239694A 1994-02-25 1994-02-25
US20239494A 1994-02-25 1994-02-25
US202,394 1994-02-25
US202,396 1994-02-25

Publications (1)

Publication Number Publication Date
WO1995022903A1 true WO1995022903A1 (fr) 1995-08-31

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AU (1) AU1758495A (fr)
WO (1) WO1995022903A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998051153A1 (fr) * 1997-05-15 1998-11-19 Rhone-Poulenc Agriculture Ltd. Procedes et derives herbicides
US5945381A (en) * 1996-04-16 1999-08-31 Basf Aktiengesellschaft Herbicidal heterocyclically annulated benzoylisothiazoles
US6046137A (en) * 1996-04-16 2000-04-04 Basf Aktiengesellschaft Herbicidal heterocyclically substituted benzoylisothiazoles
US6083879A (en) * 1996-04-16 2000-07-04 Basf Aktiengesellschaft Herbicidal benzoylisothiazoles
WO2000068227A1 (fr) * 1999-05-06 2000-11-16 Bayer Aktiengesellschaft Benzoylisoxazoles substitues et leur utilisation comme herbicides
US6297198B1 (en) 1996-05-14 2001-10-02 Syngenta Participations Ag Isoxazole derivatives and their use as herbicides
US8188009B2 (en) * 2008-03-26 2012-05-29 Bayer Cropscience Ag 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles effective as herbicides
CN104030998A (zh) * 2014-06-05 2014-09-10 华东师范大学 4-多氟烷基-4，5-二取代异噁唑衍生物及其制备方法

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EP0377892A1 (fr) * 1988-12-29 1990-07-18 BASF Aktiengesellschaft Dérivés de 3-(2H)-pyridazinone, leur procédé de production et leur utilisation comme pesticides
EP0418175A2 (fr) * 1989-09-11 1991-03-20 Rhone Poulenc Agriculture Ltd. Isoxazoles herbicides
EP0428340A1 (fr) * 1989-11-14 1991-05-22 Zeneca Limited Composés hétérocycliques
EP0457204A1 (fr) * 1990-05-18 1991-11-21 BASF Aktiengesellschaft Esters 3-isoxazolylbenzyliques, leur préparation et utilisation
EP0487357A1 (fr) * 1990-11-22 1992-05-27 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles
EP0524018A1 (fr) * 1991-07-17 1993-01-20 Rhone-Poulenc Agriculture Ltd. Isoxazoles herbicides
EP0573883A1 (fr) * 1992-06-12 1993-12-15 Bayer Ag Utilisation de dérivés d'acides 3-aryl substitué-5-alkyl-isoxazole-4-carboxyliques dans la lutte contre les endoparasites, nouveaux dérivés d'acides 3-arylsubstitué-5-alkyl-isoxazole-4-carboxyliques et procédé de préparation

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0377892A1 (fr) * 1988-12-29 1990-07-18 BASF Aktiengesellschaft Dérivés de 3-(2H)-pyridazinone, leur procédé de production et leur utilisation comme pesticides
EP0418175A2 (fr) * 1989-09-11 1991-03-20 Rhone Poulenc Agriculture Ltd. Isoxazoles herbicides
EP0428340A1 (fr) * 1989-11-14 1991-05-22 Zeneca Limited Composés hétérocycliques
EP0457204A1 (fr) * 1990-05-18 1991-11-21 BASF Aktiengesellschaft Esters 3-isoxazolylbenzyliques, leur préparation et utilisation
EP0487357A1 (fr) * 1990-11-22 1992-05-27 Rhone-Poulenc Agriculture Ltd. Dérivés de 4-benzoyl isoxazoles
EP0524018A1 (fr) * 1991-07-17 1993-01-20 Rhone-Poulenc Agriculture Ltd. Isoxazoles herbicides
EP0573883A1 (fr) * 1992-06-12 1993-12-15 Bayer Ag Utilisation de dérivés d'acides 3-aryl substitué-5-alkyl-isoxazole-4-carboxyliques dans la lutte contre les endoparasites, nouveaux dérivés d'acides 3-arylsubstitué-5-alkyl-isoxazole-4-carboxyliques et procédé de préparation

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5945381A (en) * 1996-04-16 1999-08-31 Basf Aktiengesellschaft Herbicidal heterocyclically annulated benzoylisothiazoles
US6046137A (en) * 1996-04-16 2000-04-04 Basf Aktiengesellschaft Herbicidal heterocyclically substituted benzoylisothiazoles
US6083879A (en) * 1996-04-16 2000-07-04 Basf Aktiengesellschaft Herbicidal benzoylisothiazoles
US6297198B1 (en) 1996-05-14 2001-10-02 Syngenta Participations Ag Isoxazole derivatives and their use as herbicides
WO1998051153A1 (fr) * 1997-05-15 1998-11-19 Rhone-Poulenc Agriculture Ltd. Procedes et derives herbicides
WO2000068227A1 (fr) * 1999-05-06 2000-11-16 Bayer Aktiengesellschaft Benzoylisoxazoles substitues et leur utilisation comme herbicides
AU773634B2 (en) * 1999-05-06 2004-05-27 Bayer Aktiengesellschaft Substituted benzoylisoxazoles and the use thereof as herbicides
US6838415B1 (en) 1999-05-06 2005-01-04 Bayer Aktiengesellschaft Substituted benzoylisoxazoles and the use thereof as herbicides
US8188009B2 (en) * 2008-03-26 2012-05-29 Bayer Cropscience Ag 4-(3-aminobenzoyl)-5-cyclopropylisoxazoles effective as herbicides
CN104030998A (zh) * 2014-06-05 2014-09-10 华东师范大学 4-多氟烷基-4，5-二取代异噁唑衍生物及其制备方法
CN104030998B (zh) * 2014-06-05 2015-11-18 华东师范大学 4-多氟烷基-4，5-二取代异噁唑衍生物及其制备方法

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