SU1558301A3 - Способ получени сложных эфиров циклопропанкарбоновых кислот и ненасыщенных алифатических спиртов - Google Patents
Способ получени сложных эфиров циклопропанкарбоновых кислот и ненасыщенных алифатических спиртов Download PDFInfo
- Publication number
- SU1558301A3 SU1558301A3 SU833692001A SU3692001A SU1558301A3 SU 1558301 A3 SU1558301 A3 SU 1558301A3 SU 833692001 A SU833692001 A SU 833692001A SU 3692001 A SU3692001 A SU 3692001A SU 1558301 A3 SU1558301 A3 SU 1558301A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- dimethyl
- cis
- methyl
- carboxylic acid
- oxo
- Prior art date
Links
- -1 unsaturated aliphatic alcohols Chemical class 0.000 title claims description 90
- 150000002148 esters Chemical class 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 8
- VFVUEHVSWANYJR-UHFFFAOYSA-N carbonic acid;cyclopropane Chemical class C1CC1.OC(O)=O VFVUEHVSWANYJR-UHFFFAOYSA-N 0.000 title 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- RDPCZRSHMKDXAA-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1.C1CCCCC1N=C=NC1CCCCC1 RDPCZRSHMKDXAA-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 6
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000460 chlorine Substances 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 54
- 239000000126 substance Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 17
- 241000238631 Hexapoda Species 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 239000013543 active substance Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 229960001901 bioallethrin Drugs 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
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- 244000045947 parasite Species 0.000 description 8
- ZHCNXDUZDBTSAW-UHFFFAOYSA-N 1-(3-methoxy-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid Chemical compound COC(=O)C=CC1(C(O)=O)CC1 ZHCNXDUZDBTSAW-UHFFFAOYSA-N 0.000 description 7
- 241000256059 Culex pipiens Species 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 230000001069 nematicidal effect Effects 0.000 description 6
- VZVKWLCVKPJHRK-UHFFFAOYSA-N 1-pent-1-enoxypent-1-ene Chemical compound CCCC=COC=CCCC VZVKWLCVKPJHRK-UHFFFAOYSA-N 0.000 description 5
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- 235000011613 Pinus brutia Nutrition 0.000 description 4
- 241000018646 Pinus brutia Species 0.000 description 4
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- 238000010438 heat treatment Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- HSIZPBYFVGZXMN-UHFFFAOYSA-N 1-(3-ethoxy-2-fluoro-3-oxoprop-1-enyl)cyclopropane-1-carboxylic acid Chemical compound CCOC(=O)C(F)=CC1(C(O)=O)CC1 HSIZPBYFVGZXMN-UHFFFAOYSA-N 0.000 description 3
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- 206010063409 Acarodermatitis Diseases 0.000 description 3
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- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 3
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- 239000002904 solvent Substances 0.000 description 3
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 2
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 2
- IPJJDDNHHXCXSE-UHFFFAOYSA-N 2-prop-1-enylcyclopropan-1-one Chemical compound O=C1CC1C=CC IPJJDDNHHXCXSE-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- 241000218645 Cedrus Species 0.000 description 2
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- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
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- LROBJRRFCPYLIT-UHFFFAOYSA-M magnesium;ethyne;bromide Chemical compound [Mg+2].[Br-].[C-]#C LROBJRRFCPYLIT-UHFFFAOYSA-M 0.000 description 2
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
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- RFAQWADNTLIWMG-RDDDGLTNSA-N (1r,2s)-2-ethenyl-1-[(2-methylpropan-2-yl)oxycarbonylamino]cyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)N[C@]1(C(O)=O)C[C@H]1C=C RFAQWADNTLIWMG-RDDDGLTNSA-N 0.000 description 1
- WIHMGGWNMISDNJ-UHFFFAOYSA-N 1,1-dichloropropane Chemical compound CCC(Cl)Cl WIHMGGWNMISDNJ-UHFFFAOYSA-N 0.000 description 1
- OBBWYRQXXKJCRE-UHFFFAOYSA-N 1-[3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]cyclopropane-1-carboxylic acid Chemical compound CC(C)(C)OC(=O)C=CC1(C(O)=O)CC1 OBBWYRQXXKJCRE-UHFFFAOYSA-N 0.000 description 1
- FXCXOKOKILDXCL-UHFFFAOYSA-N 1-but-2-enoxybut-2-ene Chemical compound CC=CCOCC=CC FXCXOKOKILDXCL-UHFFFAOYSA-N 0.000 description 1
- OYDPVRNLLQZQFY-UHFFFAOYSA-N 2,2-dimethyl-3-[(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical class OC(=O)C1C(C)(C)C1C=C1C(=O)SCC1 OYDPVRNLLQZQFY-UHFFFAOYSA-N 0.000 description 1
- BIDXSIRKAVZREN-UHFFFAOYSA-N 2-fluoro-3-methylbut-2-enal Chemical compound CC(C)=C(F)C=O BIDXSIRKAVZREN-UHFFFAOYSA-N 0.000 description 1
- NWVNDFGYFPBENP-UHFFFAOYSA-N 2-fluorobut-2-en-1-ol Chemical compound CC=C(F)CO NWVNDFGYFPBENP-UHFFFAOYSA-N 0.000 description 1
- XMHDLKFMJMNOAX-UHFFFAOYSA-N 2-methyl-3-(2-methylprop-2-enoxy)prop-1-ene Chemical compound CC(=C)COCC(C)=C XMHDLKFMJMNOAX-UHFFFAOYSA-N 0.000 description 1
- AWJLUXZJSVABLM-UHFFFAOYSA-N 2-oxo-1-prop-1-enylcyclopropane-1-carboxylic acid Chemical compound CC=CC1(C(O)=O)CC1=O AWJLUXZJSVABLM-UHFFFAOYSA-N 0.000 description 1
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical class CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
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- SOMAKHIBCDNYAV-UHFFFAOYSA-N 4-fluoro-5-methylhex-4-en-1-yn-3-ol Chemical compound CC(C)=C(F)C(O)C#C SOMAKHIBCDNYAV-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- XNRCGJVOJYKMSA-UHFFFAOYSA-N 5-[bis[2-(2-butoxyethoxy)ethoxy]methyl]-1,3-benzodioxole Chemical compound CCCCOCCOCCOC(OCCOCCOCCCC)C1=CC=C2OCOC2=C1 XNRCGJVOJYKMSA-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
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- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 235000019733 Fish meal Nutrition 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
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- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 101001007415 Homo sapiens LEM domain-containing protein 1 Proteins 0.000 description 1
- 102100028300 LEM domain-containing protein 1 Human genes 0.000 description 1
- 241001337998 Machilus Species 0.000 description 1
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- 241001494479 Pecora Species 0.000 description 1
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- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- 229960001506 brilliant green Drugs 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
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- 238000000151 deposition Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- CVUNPKSKGHPMSY-UHFFFAOYSA-N ethyl 2-chloroprop-2-enoate Chemical compound CCOC(=O)C(Cl)=C CVUNPKSKGHPMSY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
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- 230000003902 lesion Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- RUAIJHHRCIHFEV-UHFFFAOYSA-N methyl 4-amino-5-chlorothiophene-2-carboxylate Chemical compound COC(=O)C1=CC(N)=C(Cl)S1 RUAIJHHRCIHFEV-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
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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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8221039A FR2537973B1 (fr) | 1982-12-15 | 1982-12-15 | Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1558301A3 true SU1558301A3 (ru) | 1990-04-15 |
Family
ID=9280132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833692001A SU1558301A3 (ru) | 1982-12-15 | 1983-12-14 | Способ получени сложных эфиров циклопропанкарбоновых кислот и ненасыщенных алифатических спиртов |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS59118742A (enExample) |
| FR (1) | FR2537973B1 (enExample) |
| HU (1) | HU194800B (enExample) |
| SU (1) | SU1558301A3 (enExample) |
| ZA (1) | ZA839300B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2570698B1 (fr) * | 1984-09-26 | 1986-12-19 | Roussel Uclaf | Esters d'acides cyclopropane carboxyliques et d'alcools diacetyleniques, leur procede de preparation et leur application a la lutte contre les parasites |
| PH21875A (en) * | 1985-04-26 | 1988-03-25 | Sumitomo Chemical Co | Novel carboxylic acid esters,their method of use and insecticides containing them as the active ingredient |
| FR2586675B1 (fr) * | 1985-08-27 | 1987-12-11 | Roussel Uclaf | Nouveaux esters d'acide cyclopropane carboxylique et de 2,3 dihydro-4-phenyl-ih-inden-2-ol, leur procede de preparation et leur application a la lutte contre les parasites |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4003945A (en) * | 1973-04-20 | 1977-01-18 | Sumitomo Chemical Company, Limited | Novel cyclopropanecarboxylates |
| FR2491060A1 (fr) * | 1980-10-01 | 1982-04-02 | Roussel Uclaf | Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites |
-
1982
- 1982-12-15 FR FR8221039A patent/FR2537973B1/fr not_active Expired
-
1983
- 1983-12-14 ZA ZA839300A patent/ZA839300B/xx unknown
- 1983-12-14 HU HU834264A patent/HU194800B/hu not_active IP Right Cessation
- 1983-12-14 SU SU833692001A patent/SU1558301A3/ru active
- 1983-12-15 JP JP58235249A patent/JPS59118742A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| Патент СССР № 1210661, кл. С 07 С 69/74, 1981. Патент СССР № 1342408, кл. С 07 С 69/74, 1981. Патент FR № 2240914, кл. С 07 С 69/74, 1975. * |
Also Published As
| Publication number | Publication date |
|---|---|
| HU194800B (en) | 1988-03-28 |
| FR2537973A1 (fr) | 1984-06-22 |
| ZA839300B (en) | 1985-01-30 |
| FR2537973B1 (fr) | 1985-11-08 |
| JPH0456818B2 (enExample) | 1992-09-09 |
| JPS59118742A (ja) | 1984-07-09 |
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