WO1986001501A1 - Arthropodicides - Google Patents

Arthropodicides Download PDF

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Publication number
WO1986001501A1
WO1986001501A1 PCT/AU1985/000204 AU8500204W WO8601501A1 WO 1986001501 A1 WO1986001501 A1 WO 1986001501A1 AU 8500204 W AU8500204 W AU 8500204W WO 8601501 A1 WO8601501 A1 WO 8601501A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
group
formula
composition
ethoxyphenyl
Prior art date
Application number
PCT/AU1985/000204
Other languages
English (en)
Inventor
George Holan
Karen Elizabeth Jarvis
Wynona Marguerite Phillips Johnson
Original Assignee
Commonwealth Scientific And Industrial Research Or
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 Commonwealth Scientific And Industrial Research Or filed Critical Commonwealth Scientific And Industrial Research Or
Priority to BR8506904A priority Critical patent/BR8506904A/pt
Publication of WO1986001501A1 publication Critical patent/WO1986001501A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • 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
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
    • A01N31/14—Ethers
    • 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
    • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
    • A01N33/02—Amines; Quaternary ammonium compounds
    • A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
    • A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
    • C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen

Definitions

  • This invention relates to new compounds having arthropodicidal activity, to methods of preparing these compounds and to the use of the compounds afs arthropodicides, especially -as insecticides and acaricides.
  • R is a halo group; or a lower alkyl, lower alkoxy or lower alkylthio group, in each of which the alkyl group may be substituted with one or more halo groups;
  • R2 is hydrogen or a halo or halomethyl grou'p; or R1
  • R 2 and R together form a methylenedioxy, or a difluoro-methylenedioxy group or, R 1 and R2 together with the carbon atoms to which they are attached, form an aromatic ring;
  • X is a fluoro, chloro or bromo group
  • A' is 0, S, NH, or NZ where Z is lower alkyl or haloalkyl or cyano group;
  • R is 3-phenoxyphenyl, 2-phenoxy-6-pyr ⁇ dyl, 4-f luoro-3- henoxyphenyl , or 2-phenoxy-3- fluoro- ⁇ -pyridyl;
  • halo means fluoro, chloro or bromo; "lower” implies alkyl groups having from 1 to 4 carbon atoms. Alkyl groups having more than 2 carbon atoms may -be straight or branched.
  • R 1 and R2 are essentially as defined above and X 1, X2 are the same or different and each is fluorine, chlorine or bromine, with one of the following alcohols:- 3-phenoxybenzyl alcohol 2-benzyl-4-furylmethanol ⁇ -cyano-3-phen ⁇ xybenzyl alcohol 3 ,4-methylenedioxybenzyl alcohol -ethynyl-3-phenoxybenzyl alcohol
  • R 1 , R2 , X1 , X2 and A1- are as previously defined,
  • R 4 , R are independently hydrogen, chlorine, or fluorine
  • the compounds of the invention are optically active and can be resolved into their optical isomers by conventional methods.
  • the invention thus includes the individual optical isomers of the compounds as well as the racemic forms.
  • the compounds of formula (I) may be prepared by the conventional methods of synthetic organic chemistry.
  • the compounds are formed by reacting together compounds of the formulae (III) and ( IV)
  • R 1, R2, R3 and R4 are as defined above and wherein P and
  • Q are reactive atoms or groups, often referred to as
  • leaving groups selected so that on reaction they give rriissee ttoo tthhee ddeessiirreedd ggrroouupp AA oorr ttoo aamnother group which is convertible to that desired group.
  • the compounds (I) having the A groups listed below may be formed from the compounds (III) and (IV) having the indicated substituents P and Q.
  • the active compounds of the invention are well tolerated by plants, have a favourable level of toxicity to warm-blooded animals, and can be used for combating arthropod pests, especially insects or acarids, which are encountered in agriculture, in veterinary practice, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
  • arthropod pests especially insects or acarids, which are encountered in agriculture, in veterinary practice, in forestry, in the protection of stored products and of materials, and in the hygiene field. They are active against normally sensitive and resistant species and against all or some stages of development.
  • the abovementioned pests include Blatella germanica (German cockroach) , and Heliothis punctigera (cotton budworm) .
  • the present invention also provides arthropodicial compositions containing as active ingredients a compound of the present invention.
  • the present invention also provides a method of combating arthropods (especially insects or acarids) which comprises applying- to the arthropods, or to a habitat .thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention.
  • arthropods especially insects or acarids
  • the present invention also provides a method of freeing or protecting domesticated animals from parasitical insects or acarids which comprises applying to said animals a compound according to the present invention, or a composition containing such a compound as the active ingredient. s •
  • the active compounds are converted into such customary formulations as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, suspension-emulsion concentrates, seed-treatment powders, natural and synthetic materials impregnated with active compound, very fine capsules in polymeric substances, and coating compositions for use on seed, as well as ULV cold mist and warm mist formulations.
  • formulations may be produced in known manner, for example by mixing the active compounds with extenders, i.e., liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, i.e., emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • extenders i.e., liquid or liquefied gaseous or solid diluents or carriers
  • surface-active agents i.e., emulsifying agents and/or dispersing agents and/or foam-forming agents.
  • auxiliary solvents such as for example, organic solvents, can also be used.
  • suitable liquid diluents or carriers are aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride; aliphatic or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions; alcohols, such as butanol or glycol, as well as their ethers; and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cycl ⁇ hexanone; and strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
  • aromatic hydrocarbons such as xylene, toluene or alkyl naphthalenes
  • chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene
  • liquefied gaseous diluents or carriers liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
  • solid carriers are ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth; and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates.
  • crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite
  • synthetic granules of inorganic and organic meals such as sawdust, coconut shells, maize cobs and tobacco stalks.
  • emulsifying and/or foam-forming agents examples include non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxy ethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates, " as well as albumin hydrolysis products.
  • Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose,.
  • Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations. s
  • colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin " dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs.
  • organic dyestuffs such as alizarin " dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs.
  • the formulations in general will contain from 0.1 to 95 per cent by weight of active compound, preferably from 0.5 to 90 per cent by weight.
  • the active compounds according to the invention may be used in the form of formulations of the types that are commercially available or in the use forms prepared from these formulations.
  • the active compound content of the use forms prepared from the formulations of the types that are commercially available can vary within wide ranges.
  • the active compound concentration of the use forms can be from 0.0000001 to 100% by weight of active compound, preferably from 0.0001 to 10% by weight.
  • the compounds may be employed in a customary manner appropriate for the particular use forms.
  • the active compounds according to the invention are also suitable for combating ectoparasites and endoparasites in the field of veterinary medicine.
  • the compounds may be used in a known manner, such as orally in the form of, for example, tablets, capsules, drenches and granules; dermally by means of, for example, dipping, spraying, pouring-on, spotting-on and powdering.
  • the compounds may be employed either as the sole toxic agent in compositions such as those described above, or in combination with other insecticides such as pyrethrum, rotenone, or with fungicidal or bactericidal agents, to provide compositions useful for household and * agricultural dusts and sprays, textile coating and impregnation, and the like.
  • the compounds of the invention may be advantageously combined with other substances which have a synergistic or potentiating action.
  • substances are of the class of microsomal oxidase inhibitors, i-.e. , they inhibit the detoxification of insecticides in insects produced by the action of oxidative enzymes.
  • Typical substances of this type are the pyrethrin synergists of which the following are examples:-
  • n-Propyl isome 3-dioxole-5, ⁇ -dicarboxylate
  • propynyl ethers and propynyl oximes 3-dioxole-5, ⁇ -dicarboxylate
  • Piperonyl butoxide is particularly us_eful as a potentiator.
  • the amount of piperonyl butoxide use ' d may vary from 1/lOOth to fifty times the weight of the compound I the preferred range being from about l/100th to five parts by weight.
  • 'Sesamex' also is a useful potentiator in similar amounts. Examples of formulations in accordance with the invention are as follows: (parts are by weight) :
  • the active substance is mixed and ground with the carriers.
  • the active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, the polyethylene glycol and cetyl polyglycol ether are then added. The solution obtained is sprayed onto kaolin and the acetone is evaporated off in vacuo. Wettable powders
  • the active substance is intimately mixed in suitable mixers with the additives, and the mixture is then ground in the appropriate mills and rollers to obtain wettable powders which can be diluted with water to give suspensions of the desired concentration.
  • Emulsions of the required concentration can be prepared from these concentrates by dilution with water.
  • Ethyl 1-(4-ethoxyphenyl)-2-chloro-2-fluorocyclo- propane-1-carboxylate (lg, 3.5 mmol) was dissolved in dry xylene (2 ml) and placed under an argon atmosphere. Tri-n-butyltin hydride (lg, 3.6 mmol) and a catalyst amount of azobisisobutyronitrile (9 mg) were added to the solution. The solution was refluxed for 3 hours. At the end of this time the solution was cooled, dissolved in ether and the ether layer thoroughly washed with water. The ether layer was filtered through a short alumina (5% H_0) column and concentrated in vacuo. The residue was fractionally distilled.
  • the arthropodicidal activities of the compounds were determined according to the following Examples 3 to 5.
  • Insecticidal activity was investigated against blowfly, Lucilia cuprina.
  • the method used was as follows:- (a) The compounds were tested for activity against a dieldrin susceptible strain (BLL) which had been collected before dieldrin usage in the field.
  • BLL dieldrin susceptible strain
  • test compound was applied in acetone solution, 0.5 ⁇ l dispensed with a Drummond micropipette to the dorsum of the thorax of 2-3 day old females.
  • Adult flies were fed on water and sugar-only and maintained at 25°C and 60-70% RH. The mortalities were determined after 24 hours.. Moribund.flies were regarded as dead.
  • the LD c - values, in terms of concentration, were interpolated from the probit/log dose, relation using a computer program.
  • the compound was also tested on the insects described above in conjunction with the potentiator piperonyl butoxide by pretreating each insect with 1 ⁇ l of a 2% solution of the potentiator in acetone.
  • the mortalities were counted at 48 hours after treatment and compared with acetone and acetone/potentiator controls.
  • the LD-.- values were determined as described above and converted to Potency Index values. About the same levels of potentiation were obtained when piperonyl butoxide was replaced, by an equal amount of "Sesoxane"..
  • Insecticidal activity against the German cockroach (Blatella germanica) was determined using the following method:
  • the compound under test was applied in acetone solution at a range of concentrations. 0.5 ⁇ l was dispensed with a Drummond micropipette to the ventral thorax of adult cockroaches. The mortalities were determined after 48 hours. Moribund cockroaches were regarded as dead. The D ⁇ . values in terms of concentration were determined by probit analysis of the mortality/concentration data and converted to Potency Index values.
  • Insecticidal activity against the cotton pest Heliothis punctigera was determined using the following method:
  • the compound under test was applied in acetone solution at a range of concentrations. 0.5 ⁇ l was dispensed with a Drummond micropipette to the dorsal surface of 3rd instar larvae. Each larva was held in a separate container and was fed on spinach and maintained at 25°C and 60-70% RH. The mortalities were determined after 48 hours. Moribund larvae were regarded as dead. The LD.- n values in terms of concentration were determined by a probit analysis of the mortality/concentration data and converted to Potency Index values.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Composés à action arthropodicide, de formule générale (I), ainsi que leurs formes isomères, où R1 est un groupe halo, ou un groupe alkyle inférieur, alkoxy inférieur ou alkylthio inférieur, dans chacun desquels le groupe alkyle peut être substitué par un ou plusieurs groupes halo; R2 est hydrogène ou un groupe halo ou halométhyle; ou alors R1 et R2 forment ensemble un groupe méthylénedioxy ou un groupe difluoro-méthylènedioxy, ou alors R1 et R2, avec les atomes de carbone auxquels ils sont liés forment un anneau aromatique; X est un groupe fluoro, chloro ou bromo; A' est O, S, NH ou NZ où Z est un groupe cyano, alkyle inférieur ou haloalkyle; R3 est 3-phénoxyphényle, 2-phénoxy-6-pyridyle, 4-fluoro-3-phénoxyphényle ou 2-phénoxy-3-fluoro-6-pyridyle; R4 est hydrogène ou cyano.
PCT/AU1985/000204 1984-08-30 1985-08-27 Arthropodicides WO1986001501A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
BR8506904A BR8506904A (pt) 1984-08-30 1985-08-27 Artropodicidas

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AUPG685284 1984-08-30
AUPG6852 1984-08-30

Publications (1)

Publication Number Publication Date
WO1986001501A1 true WO1986001501A1 (fr) 1986-03-13

Family

ID=3770737

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU1985/000204 WO1986001501A1 (fr) 1984-08-30 1985-08-27 Arthropodicides

Country Status (8)

Country Link
EP (1) EP0191847A4 (fr)
JP (1) JPS62500238A (fr)
BR (1) BR8506904A (fr)
HU (1) HUT41589A (fr)
IL (1) IL76207A0 (fr)
PH (1) PH20900A (fr)
WO (1) WO1986001501A1 (fr)
ZA (1) ZA856615B (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP54A (en) * 1987-04-23 1989-09-20 Fmc Corp Insecticidal cyclopropyl-substituted di (aryl) compounds.
WO1994006741A1 (fr) * 1992-09-16 1994-03-31 British Technology Group Limited Fluoroolefines pesticides
WO2005007614A1 (fr) * 2003-07-03 2005-01-27 The Government Of The United States Of America As Represented By The Secretary, Department Of Health And Human Services 6011 Inhibiteurs d'oxydase de monoamine

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0094085A1 (fr) * 1982-05-12 1983-11-16 Sumitomo Chemical Company, Limited Composés d'éthers, leur préparation et une composition insecticide et/ou acaricide les contenant
WO1984001147A1 (fr) * 1982-09-24 1984-03-29 Commw Scient Ind Res Org Composes arthropodicides
AU2674584A (en) * 1983-04-12 1984-10-18 Ciba-Geigy Ag 3-phenoxybenzyl-(2-phenyl-2,2-alkylene-ethyl) ethers and -thioethers
WO1984004298A1 (fr) * 1983-04-25 1984-11-08 Cheminova As Derives d'ether d'arylcycloalkyle, leur utilisation et preparation
JPS59225135A (ja) * 1983-06-06 1984-12-18 Sumitomo Chem Co Ltd エ−テル誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
EP0136451A2 (fr) * 1983-09-12 1985-04-10 Schering Aktiengesellschaft Dérivés d'éthers arylméthyliques, pesticides contenant ces composés et procédé pour leur préparation

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0094085A1 (fr) * 1982-05-12 1983-11-16 Sumitomo Chemical Company, Limited Composés d'éthers, leur préparation et une composition insecticide et/ou acaricide les contenant
WO1984001147A1 (fr) * 1982-09-24 1984-03-29 Commw Scient Ind Res Org Composes arthropodicides
AU2674584A (en) * 1983-04-12 1984-10-18 Ciba-Geigy Ag 3-phenoxybenzyl-(2-phenyl-2,2-alkylene-ethyl) ethers and -thioethers
WO1984004298A1 (fr) * 1983-04-25 1984-11-08 Cheminova As Derives d'ether d'arylcycloalkyle, leur utilisation et preparation
JPS59225135A (ja) * 1983-06-06 1984-12-18 Sumitomo Chem Co Ltd エ−テル誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤
EP0136451A2 (fr) * 1983-09-12 1985-04-10 Schering Aktiengesellschaft Dérivés d'éthers arylméthyliques, pesticides contenant ces composés et procédé pour leur préparation

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See also references of EP0191847A4 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AP54A (en) * 1987-04-23 1989-09-20 Fmc Corp Insecticidal cyclopropyl-substituted di (aryl) compounds.
WO1994006741A1 (fr) * 1992-09-16 1994-03-31 British Technology Group Limited Fluoroolefines pesticides
TR27236A (tr) * 1992-09-16 1994-12-20 British Tech Group Pestisidal flüoroolefinler.
US5763700A (en) * 1992-09-16 1998-06-09 British Technology Group Limited Pesticidal fluoroolefins
WO2005007614A1 (fr) * 2003-07-03 2005-01-27 The Government Of The United States Of America As Represented By The Secretary, Department Of Health And Human Services 6011 Inhibiteurs d'oxydase de monoamine

Also Published As

Publication number Publication date
EP0191847A1 (fr) 1986-08-27
PH20900A (en) 1987-05-27
EP0191847A4 (fr) 1987-01-20
JPS62500238A (ja) 1987-01-29
BR8506904A (pt) 1986-12-09
HUT41589A (en) 1987-05-28
ZA856615B (en) 1986-06-25
IL76207A0 (en) 1985-12-31

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