FR2464253A1 - Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant - Google Patents
Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant Download PDFInfo
- Publication number
- FR2464253A1 FR2464253A1 FR7921744A FR7921744A FR2464253A1 FR 2464253 A1 FR2464253 A1 FR 2464253A1 FR 7921744 A FR7921744 A FR 7921744A FR 7921744 A FR7921744 A FR 7921744A FR 2464253 A1 FR2464253 A1 FR 2464253A1
- Authority
- FR
- France
- Prior art keywords
- dimethyl
- phenoxy
- cyclopropane
- cyano
- carboxylate
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 18
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims description 22
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000000575 pesticide Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 2,2-dichlorovinyl Chemical group 0.000 claims description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 25
- 239000002253 acid Substances 0.000 claims description 14
- 241000039077 Copula Species 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 230000000895 acaricidal effect Effects 0.000 claims description 7
- 239000002917 insecticide Substances 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 5
- 230000008025 crystallization Effects 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000000642 acaricide Substances 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 238000003408 phase transfer catalysis Methods 0.000 claims description 2
- 238000000053 physical method Methods 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 claims 1
- 239000003125 aqueous solvent Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 3
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 231100000111 LD50 Toxicity 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- 230000000749 insecticidal effect Effects 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 244000046052 Phaseolus vulgaris Species 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- IDVSZKGRCBMUQW-UHFFFAOYSA-N 2-(2,2-dichloroethenyl)-1,1-dimethylcyclopropane Chemical compound CC1(C)CC1C=C(Cl)Cl IDVSZKGRCBMUQW-UHFFFAOYSA-N 0.000 description 4
- 241001425390 Aphis fabae Species 0.000 description 4
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 241001301805 Epilachna Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 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 2
- 238000010908 decantation Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000001665 lethal effect Effects 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- LLMLSUSAKZVFOA-UJURSFKZSA-N (1S,3R)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@@H]1C(O)=O LLMLSUSAKZVFOA-UJURSFKZSA-N 0.000 description 1
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- LLMLSUSAKZVFOA-UHFFFAOYSA-N 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(O)=O LLMLSUSAKZVFOA-UHFFFAOYSA-N 0.000 description 1
- XWTGEDNUGUMEPF-UHFFFAOYSA-N 5,5-dichlorocyclohexa-1,3-diene Chemical compound ClC1(Cl)CC=CC=C1 XWTGEDNUGUMEPF-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000509418 Sarcoptidae Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
-
- 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)
- 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)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7921744A FR2464253A1 (fr) | 1979-08-30 | 1979-08-30 | Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant |
| OA57184A OA06590A (fr) | 1979-08-30 | 1980-07-24 | Esters d'acides cyclopropane carboxyliques, leur procédé de préparation et les compositions pesticides les renfermant. |
| NL8004945A NL8004945A (nl) | 1979-08-30 | 1980-08-29 | Cyclopropaancarbonzuuresters, werkwijze voor hun bereiding en deze esters bevattende pesticide samenstellingen. |
| JP11853380A JPS5634667A (en) | 1979-08-30 | 1980-08-29 | Ester of cyclopropanecarboxylic acid* its manufacture and pesticide composition containing same |
| IT49573/80A IT1145446B (it) | 1979-08-30 | 1980-08-29 | Esteri di ac di ciclopropancarbossilici loro precedimento di preparazione e composizioni pesticide cheli contengono |
| DE19803032617 DE3032617A1 (de) | 1979-08-30 | 1980-08-29 | Cyclopropancarbonsaeureester, verfahren zu deren herstellung und die sie enthaltenden pestiziden zusammensetzungen |
| GB8028014A GB2061919A (en) | 1979-08-30 | 1980-08-29 | Cyclopropane carboxylates |
| FR8102563A FR2499567A2 (fr) | 1979-08-30 | 1981-02-10 | Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7921744A FR2464253A1 (fr) | 1979-08-30 | 1979-08-30 | Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2464253A1 true FR2464253A1 (fr) | 1981-03-06 |
| FR2464253B1 FR2464253B1 (enExample) | 1984-07-27 |
Family
ID=9229206
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7921744A Granted FR2464253A1 (fr) | 1979-08-30 | 1979-08-30 | Esters d'acides cyclopropane carboxyliques, leur procede de preparation et les compositions pesticides les renfermant |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5634667A (enExample) |
| DE (1) | DE3032617A1 (enExample) |
| FR (1) | FR2464253A1 (enExample) |
| GB (1) | GB2061919A (enExample) |
| IT (1) | IT1145446B (enExample) |
| NL (1) | NL8004945A (enExample) |
| OA (1) | OA06590A (enExample) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810881A1 (de) * | 1977-03-14 | 1978-09-21 | Dow Chemical Co | Substituierte pyridylmethylester von cyclopropancarbonsaeuren und ihre verwendung als insektizide |
| DE2829329A1 (de) * | 1977-07-05 | 1979-01-25 | Ciba Geigy Ag | Cyclopropankarbonsaeureester und ihre salze mit anorganischen und organischen saeuren, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung |
-
1979
- 1979-08-30 FR FR7921744A patent/FR2464253A1/fr active Granted
-
1980
- 1980-07-24 OA OA57184A patent/OA06590A/xx unknown
- 1980-08-29 NL NL8004945A patent/NL8004945A/nl not_active Application Discontinuation
- 1980-08-29 JP JP11853380A patent/JPS5634667A/ja active Pending
- 1980-08-29 DE DE19803032617 patent/DE3032617A1/de not_active Withdrawn
- 1980-08-29 IT IT49573/80A patent/IT1145446B/it active
- 1980-08-29 GB GB8028014A patent/GB2061919A/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2810881A1 (de) * | 1977-03-14 | 1978-09-21 | Dow Chemical Co | Substituierte pyridylmethylester von cyclopropancarbonsaeuren und ihre verwendung als insektizide |
| DE2829329A1 (de) * | 1977-07-05 | 1979-01-25 | Ciba Geigy Ag | Cyclopropankarbonsaeureester und ihre salze mit anorganischen und organischen saeuren, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3032617A1 (de) | 1981-04-09 |
| IT8049573A0 (it) | 1980-08-29 |
| OA06590A (fr) | 1981-08-31 |
| JPS5634667A (en) | 1981-04-06 |
| IT1145446B (it) | 1986-11-05 |
| GB2061919A (en) | 1981-05-20 |
| NL8004945A (nl) | 1981-03-03 |
| FR2464253B1 (enExample) | 1984-07-27 |
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| ST | Notification of lapse |