PH20786A - Novel cyclopropane carboxylic acid derivatives - Google Patents

Novel cyclopropane carboxylic acid derivatives

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Publication number
PH20786A
PH20786A PH25671A PH25671A PH20786A PH 20786 A PH20786 A PH 20786A PH 25671 A PH25671 A PH 25671A PH 25671 A PH25671 A PH 25671A PH 20786 A PH20786 A PH 20786A
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PH
Philippines
Prior art keywords
group
radical
carbon atoms
see diagramm
atom
Prior art date
Application number
PH25671A
Inventor
Jacques Martel
Jean Tessier
Andre Teche
Original Assignee
Roussel Uclaf
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Publication date
Application filed by Roussel Uclaf filed Critical Roussel Uclaf
Publication of PH20786A publication Critical patent/PH20786A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C07C69/747—Chrysanthemumic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
    • 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
    • C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Emergency Medicine (AREA)
  • Environmental Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Furan Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Pyridine Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Catalysts (AREA)

Abstract

1. Claims (for the contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE) In all the possible isomer forms, the compounds with the formula (I') : see diagramm : EP0041021,P51,F1 in which the double bond has Z geometry, the cyclopropane copula is of 1R cis structure and A' represents : either an alkyl radical containing 1-18 carbon atoms, or a benzyl radical possibly substituted by one or more radicals chosen from the group constituted by alkyl radicals containing 1-4 carbon atoms, alkenyl radicals containing 2-6 carbon atoms, alkenyloxy radicals containing 2-6 carbon atoms, alkadienyl radicals containing 4-8 carbon atoms, the methylenedioxy residue, and the halogen atoms, or a see diagramm : EP0041021,P51,F2 group, in which the substituent R1 represents a hydrogen atom or a methyl radical and the substituent R2 represents a monocyclic aryl or a -CH2 -C -= CH group and notably a 5-benzyl-3-furylmethyl group, or a see diagramm : EP0041021,P51,F3 group in which R3 represents an aliphatic organic radical containing 2-6 carbon atoms and one or more carbon-carbon unsaturations and notably the radicals -CH2 -CH=CH2 , -CH2 -CH=CH-CH3 , -CH2 -CH=CH-C2 H5 , -CH2 -CH=CH-CH=CH2 , or a see diagramm : EP0041021,P51,F4 group, in which R3 retains the same significance as previously, each of R'1 and R'2 , identical or different, represents a hydrogen atom, a halogen atom, an alkyl radical containing 1-6 carbon atoms, an aryl radical containing 6-10 carbon atoms, an alkyloxycarbonyl group containing 2-5 carbon atoms, or a cyano group, or a see diagramm : EP0041021,P51,F5 group, in which B represents a CH2 group, or a C=O group, or a hetero element chosen from oxygen and sulphur, R4 represents a hydrogen atom, a methyl radical, a -CONH2 radical, a -CSNH2 radical or a -C -= CH radical R5 represents a halogen atom or a methyl radical and n represents a numeral 0, 1 or 2, and notably the 3-phenoxybenzyl, alpha-ethynyl-3-phenoxybenzyl, 3-benzoylbenzyl, 1-(3-phenoxyphenyl) ethyl or alpha-thioamido-3-phenoxybenzyl groups, or a see diagramm : EP0041021,P52,F1 group, or a see diagramm : EP0041021,P52,F2 group, in which each of the substituents R6 , R7 , R8 , R9 represents a hydrogen atom, a chlorine atom, or a methyl radical and in which S/I signifies an aromatic ring or a similar dihydro or tetrahydro ring, or a see diagramm : EP0041021,P52,F3 group, or a see diagramm : EP0041021,P52,F4 group, in which R10 represents a hydrogen atom or a CN radical, R12 represents a -CH2 - radical or an oxygen atom, R11 represents a thiazolyl or thiadiazolyl radical of which the bond with see diagramm : EP0041021,P52,F5 may be found at any one of the available positions, R12 being linked to R11 by the carbon atom situated between the sulphur atom and a nitrogen atom, or a see diagramm : EP0041021,P52,F6 group, or a see diagramm : EP0041021,P53,F1 group in which R13 represents a hydrogen atom or a CN radical, or a see diagramm : EP0041021,P53,F2 group, in which R13 is defined as above and the benzoyl radical is in position 3 or 4, or a see diagramm : EP0041021,P53,F3 group, in which R14 represents a hydrogen atom, a methyl, ethynyl or cyano radical and R15 and R16 , which are different from one another, represents a hydrogen, fluorine or bromine atom, or a see diagramm : EP0041021,P53,F4 group in which R14 is defined as above, each of the R17 's represents, independently, an alkyl group containing 1-4 carbon atoms, an alkoxy group containing 1-4 carbon atoms, an alkylthio group containing 1-4 carbon atoms, an alkylsulphonyl group containing 1-4 carbon atoms, or a trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro, or bromo group, p represents a numeral 0, 1 or 2 and B' represents an oxygen atom or a sulphur atom, and R represents an alkyl radical, linear, branched or cyclic, saturated or unsaturated, containing 1-18 carbon atoms, as well as the mixtures of these isomers. 1. Claims (for the contracting State AT) Preparation process for all the possible isomer forms, of compounds with the formula (I') : see diagramm : EP0041021,P57,F2 in which the double bond has Z geometry, A' represents : either an alkyl radical containing 1-18 carbon atoms, or a benzyl radical possibly substituted by one or more radicals chosen from the group constituted by the alkyl radicals containing 1-4 carbon atoms, the alkenyl radicals containing 2-6 carbon atoms, the alkenyloxy radicals containing 2-6 carbon atoms, the alkadienyl radicals containing 4-8 carbon atoms, the methylene dioxy residue, and the halogen atoms, or a see diagramm : EP0041021,P58,F1 group, in which the substituent R1 represents a hydrogen atom or a methyl radical and the substituent R2 represents a monocyclic aryl or a -CH2 -C -= CH group and notably a 5-benzyl-3-furylmethyl group, or a see diagramm : EP0041021,P58,F2 group, in which R3 represents an aliphatic organic radical containing 2-6 carbon atoms and or more carbon-carbon unsaturations and notably the -CH2 -CH=CH2 , -CH2 CH=CH-CH3 , -CH2 CH=CH-C2 H5 , -CH2 -CH=CH-CH=CH2 radicals, or a see diagramm : EP0041021,P58,F3 group, in which R3 retains the same significance as previously, R'1 and R'2 identical or different, each represent a hydrogen atom, a halogen atom, an alkyl radical containing 1-6 carbons atoms, an aryl radical containing 6-10 carbon atoms, an alkyloxycarbonyl group containing 2-5 carbon atoms, or a cyano group, or a see diagramm : EP0041021,P58,F4 group, in which B represents a CH2 or C=O group, or a hetero element chosen from oxygen and sulphur, R4 represents a hydrogen atom, a methyl radical, a -CONH2 radical, a -CSNH2 radical or a -C -= CH radical, R5 represents a halogen atom or a methyl radical and n represents a numerical 0, 1 or 2, and notably the 3-phenoxybenzyl, alpha-ethynyl-3-phenoxybenzyl, 3-benzoylbenzyl, 1-(3-phenoxyphenyl)ethyl or alpha-thiomado-3-phenoxybenzyl group, or a see diagramm : EP0041021,P58,F5 group or a see diagramm : EP0041021,P59,F1 group, in which each of the substituents R6 , R7 , R8 , R9 , represents a hydrogen atom, a chlorine atom or a methyl radical and in which S/I signifies an aromatic ring or a similar dihydro or tetrahydro ring, or a see diagramm : EP0041021,P59,F2 group, or a see diagramm : EP0041021,P59,F3 group in which R10 represents a hydrogen atom or a CN radical, R12 represents a -CH2 - radical or an oxygen atom, R11 represents a thiazolyl or thiadiazolyl radical of which the bond with see diagramm : EP0041021,P59,F4 may be found in any of the available positions, R12 being linked to R11 by the carbon atom situated between the sulphur atom and a nitrogen atom, or a see diagramm : EP0041021,P59,F5 group, or a see diagramm : EP0041021,P59,F6 group, in which R13 represents a hydrogen atom or a CN radical, or a see diagramm : EP0041021,P60,F1 group, in which R13 is defined as above and the benzoyl radical is in position 3 or 4, or a see diagramm : EP0041021,P60,F2 group, in which R14 represents a hydrogen atom, a methyl, ethynyl or cyano radical, and each of R15 and R16 , which are different, represents a hydrogen, fluorine or bromine atom, or a see diagramm : EP0041021,P60,F3 group, in which R14 is defined as above, each of the R17 's represents, independently, an alkyl group containing 1-4 carbon atoms, an alkoxy group containing 1-4 carbon atoms, an alkylthio group containing 1-4 carbon atoms, an alkylsulphonyl group containing 1-4 carbon atoms, or a trifluoromethyl, 3,4-methylenedioxy, chloro, fluoro or bromo group, p represents a numeral 0, 1 or 2 and B' represents an oxygen atom or a sulphur atom, and R represents an alkyl radical, linear branched or cyclic, saturated or unsaturated, containing 1-18 carbon atoms, as well as the mixtures of these isomers, characterized in that an acid with the formula (II) : see diagramm : EP0041021,P60,F4 in which the double bond has Z geometry, R being defined as previously, or a functional derivative of this acid, is submitted to the action of an alcohol with the formula (III) : A'OH in which A' retains the same significance as previously, and in this way the corresponding compound with the formula (I') is obtained.
PH25671A 1980-05-23 1981-05-25 Novel cyclopropane carboxylic acid derivatives PH20786A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8011569A FR2482955A1 (en) 1980-05-23 1980-05-23 NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, PROCESS FOR PREPARING THEM AND THEIR APPLICATION TO THE FIGHT AGAINST PARASITES

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PH20786A true PH20786A (en) 1987-04-14

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Country Status (25)

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EP (1) EP0041021B1 (en)
JP (3) JPS5711943A (en)
KR (1) KR840001341B1 (en)
AT (1) ATE8616T1 (en)
BR (1) BR8103240A (en)
CA (2) CA1242647A (en)
DD (2) DD159068A5 (en)
DE (1) DE3165037D1 (en)
DK (1) DK163918C (en)
EG (1) EG15439A (en)
ES (2) ES502428A0 (en)
FI (1) FI78902C (en)
FR (1) FR2482955A1 (en)
GR (1) GR81534B (en)
HU (1) HU191031B (en)
IE (1) IE52150B1 (en)
IL (1) IL62914A (en)
MA (1) MA19150A1 (en)
NZ (1) NZ197175A (en)
OA (1) OA06818A (en)
PH (1) PH20786A (en)
PT (1) PT73078B (en)
SU (1) SU1342408A3 (en)
ZA (1) ZA813384B (en)
ZW (1) ZW12181A1 (en)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
OA06786A (en) * 1980-04-16 1982-12-31 Roussel Uclaf New derivatives of cyclopropane acid, their preparation, their application to the fight against parasites of plants and animals, the compositions containing them and the new intermediates obtained.
FR2491060A1 (en) * 1980-10-01 1982-04-02 Roussel Uclaf PYRETHRIC ACID-RELATED CARBOXYLIC CYCLOPROPANIC ACID ESTERS, METHOD FOR THE PREPARATION THEREOF AND THEIR USE IN THE FIGHT AGAINST PESTS
FR2536389B2 (en) * 1982-11-22 1986-06-27 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS RELATED TO PYRETRIC ACID, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO PEST CONTROL
FR2500451B1 (en) * 1981-02-26 1986-09-26 Roussel Uclaf ESTERS OF HETEROCYCLIC ALCOHOLS DERIVED FROM THIAZOLE OR THIADIAZOLE, PROCESS FOR THEIR PREPARATION AND PESTICIDE COMPOSITIONS CONTAINING THEM
FR2517677B1 (en) * 1981-12-09 1986-05-16 Roussel Uclaf NOVEL ETHERS WITH ORGANIC REMAINS CONTAINING CHIRAL ATOMS, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO THE SPLITTING OF ALCOHOLS OR CERTAIN HEMIACETAL STRUCTURE COMPOUNDS.
FR2526017B1 (en) * 1982-04-30 1985-10-11 Roussel Uclaf ESTER OF CYCLOPROPANE CARBOXYLIC ACID AND CYANO (4-FLUORO 3-PHENOXYPHENYL) METHYLIC ALCOHOL (S), PREPARATION METHOD THEREOF AND PESTICIDE COMPOSITIONS CONTAINING THE SAME
FR2526018A1 (en) * 1982-04-30 1983-11-04 Roussel Uclaf Alpha cyano phenoxy cyclopropane carboxylate(s) - are low toxicity insecticides and acaricides for plants, animals, and buildings
US4505738A (en) * 1982-05-10 1985-03-19 Ciba-Geigy Corporation Halovinyl-3,3-dimethylcyclopropanecarboxylic acid pyronyl esters useful for the protection of cultivated plants against the harmful effects of herbicides
FR2533416B1 (en) * 1982-09-29 1988-09-02 Roussel Uclaf NOVEL PESTICIDE COMPOSITIONS CONTAINING A PHOTOSTABILIZER
FR2539411B2 (en) * 1983-01-17 1986-04-25 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, THEIR PREPARATION METHOD, THEIR APPLICATION TO THE CONTROL OF PESTS
FR2574403B1 (en) * 1984-12-06 1987-01-30 Roussel Uclaf NOVEL ESTERS DERIVED FROM CYCLOPROPANE CARBOXYLIC ACID AND (R) 2- (6-PHENOXY PYRIDYL) ETHANOL, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO PEST CONTROL
FR2586675B1 (en) * 1985-08-27 1987-12-11 Roussel Uclaf NOVEL ESTERS OF CYCLOPROPANE CARBOXYLIC ACID AND 2,3 DIHYDRO-4-PHENYL-IH-INDEN-2-OL, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO PEST CONTROL
FR2610624B1 (en) * 1987-02-06 1989-06-09 Roussel Uclaf NOVEL ESTERS OF PYRETHRIC ACID-LIKE CYCLOPROPANECARBOXYLIC ACIDS, THEIR PREPARATION PROCESS AND THEIR APPLICATION TO PEST CONTROL
JP2570388B2 (en) * 1988-06-10 1997-01-08 住友化学工業株式会社 Carboxylic acid esters and their use as insecticides
US5055491A (en) * 1989-04-10 1991-10-08 Sumitomo Chemical Company, Limited Carboxylic acid esters, methods for producing them and insecticides and/or acaricides containing them as an active ingredient
FR2678611B1 (en) * 1991-07-04 1995-01-20 Roussel Uclaf NOVEL PYRETHRINOUID ESTERS OF ALCOHOL 1,3,4,5,6,7-HEXAHYDRO 1,3-DIOXO-2H-ISOINDOL-2-YL-METHYLIQUE, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS PESTICIDES.
FR2678609B1 (en) * 1991-07-04 1994-08-26 Roussel Uclaf NOVEL PYRETHRINOUID ESTERS OF THE ALCOHOL 4-AMINO 2,3,5,6-TETRAFLUOROPHENYL METHYLIQUE, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS PESTICIDES.
FR2687149B1 (en) * 1992-02-12 1995-11-03 Roussel Uclaf NOVEL PYRETHRINOUID ESTERS DERIVED FROM THIAZOLIC ALCOHOLS, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS PESTICIDES.
CN1138752C (en) * 1995-02-07 2004-02-18 大日本除虫菊株式会社 Novel carboxylic ester derivatives, process for producing same, and insecticide or insectifuge contg. same
US5852048A (en) * 1995-03-01 1998-12-22 Sumitomo Chemical Company, Limited Ester compound and a pesticidal agent containing the same as an active ingredient
JP4488765B2 (en) * 2004-02-26 2010-06-23 大日本除蟲菊株式会社 Aerosol insecticide
CN101166722A (en) 2005-04-29 2008-04-23 惠氏公司 Process for preparing 3,3-disubstituted oxindoles and thio-oxindoles

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JPS515450B1 (en) * 1971-06-29 1976-02-20
DE2326077C2 (en) * 1972-05-25 1985-12-12 National Research Development Corp., London Unsaturated cyclopropanecarboxylic acids and their derivatives, their preparation and insecticides containing them
CH589408A5 (en) * 1973-04-18 1977-07-15 Ciba Geigy Ag
DE2706222A1 (en) * 1976-02-16 1977-08-18 Ciba Geigy Ag CYCLOPROPANCARBONIC ACID ESTERS, METHOD OF MANUFACTURING AND USING them
US4242357A (en) * 1976-04-09 1980-12-30 Bayer Aktiengesellschaft Carboxylic acid esters for combating pests
CA1117673A (en) * 1977-12-29 1982-02-02 Hajime Shichijo Tuning apparatus
HU176938B (en) * 1978-02-23 1981-06-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing new chrysanthemic acid ester derivatives
HU176939B (en) * 1978-02-23 1981-06-28 Chinoin Gyogyszer Es Vegyeszet Process for pproducing derivatives of esters of chrisanthemic acid

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IE52150B1 (en) 1987-07-08
FI78902B (en) 1989-06-30
JPH05306248A (en) 1993-11-19
DD206731A5 (en) 1984-02-08
DK163918B (en) 1992-04-21
DK163918C (en) 1992-09-14
JPH0699354B2 (en) 1994-12-07
GR81534B (en) 1984-12-11
IE811151L (en) 1981-11-23
EP0041021B1 (en) 1984-07-25
ES8300080A1 (en) 1982-10-01
IL62914A0 (en) 1981-07-31
DD159068A5 (en) 1983-02-16
FI78902C (en) 1989-10-10
FI811566L (en) 1981-11-24
CA1242647A (en) 1988-10-04
JPS60214761A (en) 1985-10-28
PT73078B (en) 1983-02-08
JPS6248660B2 (en) 1987-10-15
ES8304914A1 (en) 1983-03-16
KR830006166A (en) 1983-09-17
ZW12181A1 (en) 1981-10-14
JPS5711943A (en) 1982-01-21
CA1237433A (en) 1988-05-31
DK225881A (en) 1981-11-24
ZA813384B (en) 1982-06-30
EP0041021A3 (en) 1982-03-03
KR840001341B1 (en) 1984-09-19
SU1342408A3 (en) 1987-09-30
FR2482955A1 (en) 1981-11-27
JPH0563461B2 (en) 1993-09-10
ES512286A0 (en) 1983-03-16
PT73078A (en) 1981-06-01
ATE8616T1 (en) 1984-08-15
FR2482955B1 (en) 1983-11-18
MA19150A1 (en) 1981-12-31
BR8103240A (en) 1982-02-16
OA06818A (en) 1982-12-31
EP0041021A2 (en) 1981-12-02
ES502428A0 (en) 1982-10-01
EG15439A (en) 1986-06-30
IL62914A (en) 1986-10-31
NZ197175A (en) 1984-08-24
DE3165037D1 (en) 1984-08-30
HU191031B (en) 1986-12-28

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