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WO1989000562A1 - Pyrazolines insecticides - Google Patents

Pyrazolines insecticides Download PDF

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Publication number
WO1989000562A1
WO1989000562A1 PCT/US1988/002335 US8802335W WO8900562A1 WO 1989000562 A1 WO1989000562 A1 WO 1989000562A1 US 8802335 W US8802335 W US 8802335W WO 8900562 A1 WO8900562 A1 WO 8900562A1
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WO
WIPO (PCT)
Prior art keywords
och
alkyl
compound according
methyl
halogen
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Ceased
Application number
PCT/US1988/002335
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English (en)
Inventor
George Philip Lahm
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of WO1989000562A1 publication Critical patent/WO1989000562A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • triphenylpyrazolines and agricultural compositions containing them are useful as insecticides.
  • R 1 is a phenyl group
  • R 2 is a halogenalkoxy, halogenalkenyloxy, halogenalkylthio, halogenalkenylthio, halogenalkylsulfonyl or halogenalkenylsulfonyl group having 1 to 6 carbon atoms;
  • X and Y represent hydrogen or halogen.
  • R is alkoxycarbonyl
  • X and Y are hydrogen or halogen, and n is 2, 3, or 4.
  • R 1 is phenyl
  • R 4 is hydrogen or lower alkyl
  • X is hydrogen or halogen
  • Y and Z are hydrogen, halogen, lower alkyl, lower alkoxy, nitro, trifluoromethyl, lower alkylthio, acyl, nitrile, lower alkyl- sulfonyl, lower alkoxycarbonyl, A-R 5 or Y and Z form
  • A is O, S, SO, or SO 2 and R 5 is halogen- substituted lower alkyl.
  • R 1 is hydrogen, alkyl or alkenyl;
  • X is oxygen or sulfur;
  • R 2 is halogen, alkyl, haloalkyl, cyano, nitro, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulfonyloxy, alkylsulfonyl, alkoxycarbonyl or acyl, or two adjacent R 2 groups may form a ring;
  • m is 0 to 4;
  • R c is phenyl, para substituted by R 4 ;
  • R 4 and R 5 are R 8 SO 2 O, hydrogen, halogen, alkyl, haloalkoxy, alkylthio or alkylsulfonyl, wherein R 8 is alkyl or haloalkyl; at least one of R 4 and R 5 is R 8 SO 2 O, or R 4 is haloalkoxy.
  • a and B are phenyl or substituted phenyl; U is O or S; V is hydrogen, cycloalkyl, aryl or R 4 -Q; Y is unsubstituted or substituted alkyl, unsubstituted or substituted aryl; and Z is cycloalkyl, unsubstituted or substituted aryl or R 4 -Q provided that Z is not hydrogen and Z is not methyl when Y is methyl; and
  • R 4 -Q is broadly defined.
  • U.S. Patent 4,156,007 discloses insecticidal compounds of the formula
  • R 1 is phenyl or substituted phenyl
  • R 2 and R 3 are equal or different and have the meanings of an alkyl group, a cycloalkyl group, a pyridyl or thienyl group which may be substituted with halogen, alkyl or nitro, a phenyl group or a phenyl group substituted with 1-2 substituents selected from the group consisting of a halogen atom, an alkyl group possibly Substituted with halogen, a cycloalkyl group, an alkylthio group, an alkoxy group, a mono or dialkylamino group, a nitro group, a phenyl group possibly substituted with halogen, and a cyano group;
  • R 4 is hydrogen or alkyl; and X is oxygen or sulfur.
  • This invention pertains to compounds of Formula I, including all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use as insecticides:
  • R 1 , R 2 and R 3 are independently selected from R 8 , halogen, CN, N 3 , SCN, NO 2 , OR 8 , SRg, S(O)R 8 , S(O) 2 R 8 , OC(O)R 8 , OS(O) 2 R 8 , C(O)OR 8 , C(O)R 8 , C(O)NR 8 R 9 , S(O) 2 NR 8 R 9 , NR 8 R 9 , NR 9 C(O)R 8 , OC(O)NHR 8 , NR 9 C(O)NHR 8 and NR 9 S(O) 2 R 8 , or when m, n or p is 2, R 1 , R 2 or R 3 can be taken together as OCH 2 O, OCH 2 CH 2 O or CH 2 CH 2 O, to form a 5 or 6 membered ring, each of which can be substituted with 1 to 4 halogen atoms or 1 to 2 methyl groups;
  • R 5 is selected from C(O)OR 10 , C(O)R 10 ,
  • R 6 is H or C1 to C 4 alkyl
  • R 7 is H or CH 3 ;
  • R 8 and R 10 are independently selected from H, C 1 to C 4 alkyl, C 3 to C 4 alkenyl, C 3 to C 4 alkynyl, C 1 to C 4 haloalkyl, C 3 to C 4 haloalkenyl, C 1 to C 4 alkyl substituted with CN, C(O)OCH 3 , C(O)OCH 2 CH 3 , OCH 3 , OCH 2 CH 3 , SCH 3 , SCH 2 CH 3 and NO 2 , and phenyl or benzyl, either optionally substituted with W, or R 8 and R 9 can be taken together as (CH 2 ) 4 ,
  • R 9 and R 11 are independently selected from H, C 1 to C 4 alkyl, C 3 to C 4 alkenyl, C 3 to C 4 alkynyl, and C 1 to C 4 haloalkyl, or R 10 and R 11 can be taken together as (CH 2 ) 4 , (CH 2 ) 5 or CH 2 CH 2 OCH 2 CH 2 ; m and n are independently 0 to 5; p is 0 to 4; W is selected from halogen, CN, NO 2 , C 1 to C 2 alkyl, C 1 to C 2 haloalkyl, C 1 to C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 to C 2 alkylthio, C 1 to C 2 haloalkylthio, C 1 to C 2 alkylsulfonyl or C 1 to C 2 haloalkyl- sulfonyl; X is O or S; and
  • Y is selected from H, C 1 to C 6 alkyl, C 2 to C 6 alkoxyalkyl, CHO, C 2 to C 6 alkylcarbonyl, C 2 to C 6 alkoxycarbonyl, C 2 to C 6 haloalkylcarbonyl, C 1 to C 6 alkylthio, C 1 to C 6 haloalkylthio, phenylthio, and phenylthio substituted with 1 to 3 substituents independently selected from W.
  • Preferred compounds A are those of Formula I wherein: R 6 is H;
  • R 7 is H; n and p are independently 0 to 2; and m is 1 to 2.
  • Preferred compounds B are preferred compounds A wherein:
  • R 1 , R 2 , and R 3 are independently R 8 , halogen, CN, NO 2 , OR 8 , SR 8 , S(O)R 8 , S(O) 2 R 8 or NR 8 R 9 , or when m, n or p is 2, R 1 , R 2 or R 3 can be taken together as OCH 2 O, OCH 2 CH 2 O or CH 2 CH 2 O, each of which can be substituted with 1 to 4 halogen atoms or 1 to 2 methyl groups; R 8 is C 1 to C 2 alkyl, C 3 to C 4 alkenyl, C 1 to C 2 haloalkyl, C 3 to C 4 haloalkenyl or phenyl optionally substituted with halogen; R 9 is H or C 1 to C 2 alkyl; and X is O.
  • Preferred compounds C are preferred compounds B wherein:
  • R 1 is halogen, CN, NO 2 , OCF 2 H, OCF 3 OCF 2 CF 2 H, CF 3 or when m is 2 then R 1 may be taken together as CH 2 C(CH 3 ) 2 O or CF 2 CF 2 O to form a 5 membered ring.
  • R 2 is H, halogen, CN, N0 2 , OCH 3 , OCF 2 H,
  • R 5 is C(O)OR 10 , C(O)R 10 , C(O)NR 10 R 11 or S(O) 2 NR 10 R 11 ;
  • R 10 is H, C 1 to C 4 alkyl, C 3 to C 4 alkenyl, C 3 to C 4 alkynyl, C 1 to C 4 haloalkyl, C 3 to C 4 haloalkenyl, C 1 to C 4 alkyl substituted with CN, C(O)OCH 3 , C(O)OCH 2 CH 3 , OCH 3 , OCH 2 CH 3 , SCH 3 , SCH 2 CH 3 and NO 2 ;
  • R 11 is H or C 1 to C 2 alkyl;
  • Y is H, C 1 to C 6 alkyl, CHO, C 2 to C 6 alkylcarbonyl or C 2 to C 6 alkoxycarbonyl.
  • Preferred compounds D are preferred compounds C wherein: R 5 is C(O)OR 10 ;
  • R 10 is C 1 to C 3 alkyl, C 2 to C 3 haloalkyl, propargyl or allyl; and one of R 3 or R 5 is in the para-position and one of R 1 is in the para-position; and Y is H, CH 3 C(O)CH 3 , C(O)OCH 3 or CHO.
  • a compound of Preferred D which is methyl 4-[3-(4-chlorophenyl)-1-[(4-chlorophenyl) aminocarbonyl]-4,5-dihydro-1H-pyrazol-4- yl] benzoate; G. A compound of Preferred D which is methyl
  • R 7 are equal to hydrogen, can be found in U.S.
  • the intermediate deoxybenzoin of Formula II can be prepared by various procedures known in the art. The particular method chosen will depend on the substituents R 2 , R 3 , and R 5 and their compatibility with the conditions and reagents of that method.
  • compounds of Formula II, where R 5 is alkoxycarbonyl or dialkylsulfamoyl can be prepared by the alkylation of a trimethylsilyl cyanohydrin of Formula III with a benzyl halide of Formula IV followed by conversion of the alkylated trimethylsilyl cyanohydrin to the corresponding carbonyl. The alkylation is typically run.
  • Trimethylsilyl cyanohydrins of Formula III can be prepared from the corresponding benzaldehyde derivatives by reaction with trimethylsilylnitrile in the presence of a Lewis acid catalyst such as zinc iodide; see Evans et al., J. Chem. Soc. Chem. Comm., 55 (1973).
  • R 1 or R 2 substitutents designated as disubstituted with two open termini are bound to phenyl to form a bicyclic ring such that the first numerical designation defines the position of the first listed terminus and the second numerical designation defines the position of the other terminus.
  • the compounds of this invention will generally be used in formulation with a carrier comprising a liquid or solid diluent or an organic solvent.
  • Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like. Many of these can be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation.
  • the formulations broadly, contain about 1% to 99% by weight of active ingredient(s) and at least one of a) about 0.1% to 20% surfactant(s) and b) about 5% to 99% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:
  • Emulsions, Solutions, (including Emulsifiable Concentrates) are Emulsions, Solutions, (including Emulsifiable Concentrates).
  • compositions Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound.
  • Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0°C.
  • the ingredients are combined and stirred with gentle warming to speed solution.
  • a fine screen filter is included in packaging operation to insure the absence of any extraneous undissolved material in the product.
  • the active ingredient is blended with the inert materials in a blender. After grinding in a hammermili, the material is reblended and sifted through a U.S.S. 50 mesh screen and packaged.
  • Example 4 Dust wettable powder of Example 2 5% pyrophyllite (powder) 95%
  • the wettable powder and the pyrophyllite diluent are thoroughly blended and then packaged.
  • the product is suitable for use as a dust.
  • Example 5 Granule methyl 4-[3-(4-chlorophenyl)-4,5-dihydro-1-[[4- (trifluoromethyl)phenylamino]carbonyl]-1H- pyrazol-4-yl]benzoate 10% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No.
  • the active ingredient is dissolved in a suitable solvent and sprayed onto dedusted attapulgite granules in a double cone blender. The granules are warmed to drive off solvent, cooled and packaged.
  • Example 6 Granule wettable powder of Example 2 15% gypsum 69% potassium sulfate 16%
  • the ingredients are blended in a rotating mixer and water is sprayed on to accomplish granulation.
  • the desired range 0.1 to 0.42 mm (U.S.S. No. 18 to 40 sieves)
  • the granules are removed, dried, and screened. Oversize material is crushed to produce additional material in the desired range. These granules contain 12% active ingredient.
  • the ingredients are ground together in a sand mill until the solid particles have been reduced to under 5 microns.
  • the resulting thick suspension may be applied directly, but preferable after being extended with oils or emulsified in water.
  • the active ingredient is blended with the inert materials in a blender. After griding in a hammermill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. 50 mesh screen and packaged.
  • Compounds of Formula I can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, or other biologically active compounds to form a multi- component pesticide giving an even broader spectrum of effective agricultural protection.
  • Examples of other agricultural protectants with which compounds of the present invention can be mixed or formulated are:
  • Additional insecticides are listed Hereafter by their common names: triflumuron, diflubenzuron, methoprene, buprofezin, thiodicarb, acephate, azinphos-methyl, chlorpyrifos, dimethoate, fonophos, isofenphos, methidathion, methamidiphos, monocrotophos, phosmet, phosphamidon, phosalone, pirimicarb, phorate, profenofos, terbufos, trichlorfon, methoxychlor, bifenthrin, biphenate, cyfluthrin, fenpropathrin, fluvalinate, flucythrinate, tralomethrin, metaldehyde and rotenone, Fungicides: methyl 2-benzimidazolecarbamate (carbendazim) tetramethylthiuram disulfide (thiuram) n-
  • Acaricides senecioic acid, ester with 2-sec-butyl-4,6-dinitrophenol (binapacryl) 6-methy1-1,3-dithiolo[4,5- ⁇ ]quinoxalin-2-one (oxythioquinox) ethyl 4,4'-dichlorobenzilate (chlorobenzilate) 1,1-bis(p-chlorophenyl)-2,2,2-trichloroethanol (dicofol) bis(pentachloro-2,4-cyclopentadien-1-yl) (dienochlor) tricyclohexyltin hydroxide (cyhexatin) trans-5-(4-chlorophenyl)-N-cyclohexyl-4-methyl-2-oxothiazolidine-3-carboxamide (hexythiazox) amitraz propargite fenbutatin-oxide bisclofentezin.
  • the compounds of the present invention exhibit activity against a wide spectrum of foliar and soil inhabiting insects. Those skilled in the art will recognize that not all compounds will be equally effective against all insects, but compounds of this invention display control of many of the economically important pest species of the insect orders
  • Lepidoptera Lepidoptera, Homoptera, and Coleoptera among many others.
  • the specific species for which control is exemplified below are: fall armyworm, Spodoptera frugjperda; boll weevil, Anthonomus grandis; European corn borer, Ostrinia nubilalis; southern corn rootworm, Diabrotica undecimpunctata howardi; aster leafhopper, Macrosteles fascifrons.
  • the pest control afforded by the compounds of the present invention is not limited, however, to these species.
  • Insects are controlled and agricultural crops are protected by applying one or more of the Formula I compounds of this invention, in an effective amount, to the locus of infestation, to the area to be protected (the environment of the pests), or directly on the pests to be controlled.
  • a preferred method of application is by spraying with spray equipment that distributes the compound on the foliage, in the soil, or to the plant part that is infested or needs to be protected.
  • granular formulations of these compounds can be applied to soil or foliage or, optionally, incorporated into the soil. Either aerial or ground application can be used.
  • the pyrazoline compound(s) of this invention can be applied in its (their) pure state, but most often application will be of a formulation comprising one or more compounds of this invention, in an agriculturally suitable carrier or diluent.
  • a most preferred method of application involves spraying a water dispersion or refined oil solution of the compounds.
  • the rate of application of the Formula I compounds required for effective control wi ll depend on such factors as the insect species population size, the pest's life stage, insect size, its location, the host crop, the host stage, time of year of application, placement of the insecticide, temperature conditions, and others. In general, application rates of 0.05 to 2 kg of active ingredient per hectare are sufficient to provide effective control in large scale field operations under normal circumstances, but as little as 0.01 kg/hectare may be sufficient or as much as 8 kg/hectare may be required, depending upon the factors listed above.
  • Examples 10 to 15 demonstrate the control efficacy of compounds of Formula I on specific insect pests.
  • Compounds 1 through 115 in these tests are described in Table 4.
  • R 6 , R 7 and Y are hydrogen and X is oxygen with the following exceptions: in compound 81, Y is methyl and in compounds 104 to 106, R 6 is methyl.
  • Example 10 Fall Armvworm A test unit consisted of an 8-ounce plastic cup containing a layer of wheat germ diet, approximately 0.5 cm thick infested with ten third-instar larvae of fall armyworm (Spodoptera frugiperda). Solutions of each of the above-listed test compounds were made by combining the compound in an acetone/distilled water 75/25 solvent and then sprayed onto the cups; a single solution per cup replicated three times. Spraying was accomplished by passing the cups, on a conveyor belt, directly beneath a flat fan hydraulic nozzle which discharged the spray at a rate of 0.5 pounds of active ingredient per acre (about 0.55 kg/ha) at 30 p.s.i. The cups were then covered and held at 27°C and 50% relative humidity for 72 hours, after which time mortality readings were taken. Tested compounds which killed 80% or more of the larvae are listed below:
  • Example 11 Tobacco Budworm The test procedure of Example 10 was repeated for efficacy against third-instar larvae of the tobacco budworm (Heliothis virescens) except that mortality was assessed at 48 hours. Tested compounds which killed 80% or more of the larvae are listed below:
  • Example 12 European Corn Borer A test unit consisted of an 8-ounce plastic cup containing a one-inch square of wheat germ/soyflour diet infested with five third-instar larvae of the European corn borer (Ostrinia nubilalis). Test units were sprayed as described in Example 10. The cups were then covered and held at 27°C and 50% relative himidity for 48 hours, after which time mortality readings were taken. Tested compounds which killed 80% or more of the larvae are listed below:
  • Example 13 Southern Corn Rootworm A test unit consisted of an 8-ounce plastic cup containing 1 sprouted corn seed. The test units were sprayed as described in Example 10. After the treated cup had dried it was infested with five third-instar larvae of the Southern corn rootworm (Diabrotica undecimpunctata howardi) and replicated three times. A moistened dental wick was inserted into each cup to prevent drying and the cups were covered. The cups were then held at 27°C and 50% humidity for 48 hours, after which time mortality readings were taken. Tested compounds which killed 80% or more of the larvae are listed below: 8
  • Example 14 Boll Weevil The test unit consisted of five adult boll weevils (Anthonomus grandis) in a 9-ounce cup. The test procedure employed was the same as in Example 10. Mortality readings were taken 48 hours after treatment. Tested compounds which killed 80% or more of the adults are listed below: 1 15
  • Example 15 Aster Leafhopper A test unit was a 12-ounce cup containing oat (Avena sativa) seedlings in a 1-inch layer of sterilized soil. Test units were sprayed as described in Example 10. After the treated oats had dried between 10 and 15 adult aster leafhoppers (Mascrosteles fascifrons) were aspirated into each of the covered cups. The cups were held at 27°C and 50% relative humidity for 48 hours, and evaluated for mortality. Tested compounds which killed 80% or more of the insects are 22, 49, 50, 58 and 91.

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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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Des dérivés de pyrazoline de formule (I) dans laquelle R1, R2 et R3 sont indépendamment sélectionnés à partir de l'hydrogène ou de substituants organiques ou inorganiques définis; R5 représente un substituant d'acide, d'ester ou d'amide carboxylique ou un groupe sulfonamide; R6 et R7 représentent H ou un alkyl; m, n et p représentent zéro ou des nombres entiers; X représente O ou S; Y représente H ou un substituant organique; présentent une activité contre une large variété d'insectes foliaires ou habitant dans le sol, et peuvent donc être utilisés pour protéger les cultures.
PCT/US1988/002335 1987-07-17 1988-07-15 Pyrazolines insecticides Ceased WO1989000562A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US7479587A 1987-07-17 1987-07-17
US074,795 1987-07-17

Publications (1)

Publication Number Publication Date
WO1989000562A1 true WO1989000562A1 (fr) 1989-01-26

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Application Number Title Priority Date Filing Date
PCT/US1988/002335 Ceased WO1989000562A1 (fr) 1987-07-17 1988-07-15 Pyrazolines insecticides

Country Status (4)

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EP (1) EP0367796A1 (fr)
JP (1) JPH02504273A (fr)
AU (1) AU1993988A (fr)
WO (1) WO1989000562A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5380718A (en) * 1990-05-15 1995-01-10 E. I. Du Pont De Nemours And Company Arthropodicidal fused tetrahydropyridazines
WO2010093595A1 (fr) 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5164510B2 (ja) * 2006-10-06 2013-03-21 日本曹達株式会社 含窒素複素環化合物および有害生物防除剤
JP5164525B2 (ja) * 2006-11-01 2013-03-21 日本曹達株式会社 含窒素へテロ環化合物および有害生物防除剤

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2529689A1 (de) * 1974-07-12 1976-01-29 Philips Nv Neue pyrazolinverbindungen
EP0021506A2 (fr) * 1979-07-03 1981-01-07 Duphar International Research B.V Dérivés de la pyrazoline, procédé pour leur préparation ainsi qu'une composition insecticide les contenant
EP0153127A2 (fr) * 1984-02-16 1985-08-28 Rohm And Haas Company N-Aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides, procédés pour leur préparation, compositions insecticides les contenant et procédés pour combattre les insectes
GB2166137A (en) * 1984-10-25 1986-04-30 Fmc Corp Pyrazoline insecticides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2529689A1 (de) * 1974-07-12 1976-01-29 Philips Nv Neue pyrazolinverbindungen
EP0021506A2 (fr) * 1979-07-03 1981-01-07 Duphar International Research B.V Dérivés de la pyrazoline, procédé pour leur préparation ainsi qu'une composition insecticide les contenant
EP0153127A2 (fr) * 1984-02-16 1985-08-28 Rohm And Haas Company N-Aryl-3-aryl-4,5-dihydro-1H-pyrazole-1-carboxamides, procédés pour leur préparation, compositions insecticides les contenant et procédés pour combattre les insectes
GB2166137A (en) * 1984-10-25 1986-04-30 Fmc Corp Pyrazoline insecticides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5380718A (en) * 1990-05-15 1995-01-10 E. I. Du Pont De Nemours And Company Arthropodicidal fused tetrahydropyridazines
US5591729A (en) * 1990-05-15 1997-01-07 E. I. Du Pont De Nemours And Company Arthropodicidal tetrahydropyridazines
WO2010093595A1 (fr) 2009-02-10 2010-08-19 E. I. Du Pont De Nemours And Company 2‑pyridones fongicides

Also Published As

Publication number Publication date
EP0367796A1 (fr) 1990-05-16
AU1993988A (en) 1989-02-13
JPH02504273A (ja) 1990-12-06

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