JPS61275251A - シクロプロパンカルボン酸とジアセチレンアルコ−ルとのエステル、それらの製造法、寄生虫の駆除への使用及びそれらを含む組成物 - Google Patents

シクロプロパンカルボン酸とジアセチレンアルコ−ルとのエステル、それらの製造法、寄生虫の駆除への使用及びそれらを含む組成物

Info

Publication number: JPS61275251A
Authority: JP; Japan
Prior art keywords: formula; compound; alcohol; group; parasites
Prior art date: 1984-09-26
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.): Pending

Application number

JP60210355A

Other languages

English (en)

Japanese (ja)

Inventor

ジヤン・テシエ

アンドレ・テシユ

ジヤン・ピエール・ドムート

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.)

Sanofi Aventis France

Original Assignee

Roussel Uclaf SA

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.)

1984-09-26

Filing date

1985-09-25

Publication date

1986-12-05

1985-09-25 Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA

1986-12-05 Publication of JPS61275251A publication Critical patent/JPS61275251A/ja

Status Pending legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims description 48
150000002148 esters Chemical class 0.000 title claims description 15
-1 diacetylene alcohols Chemical class 0.000 title claims description 8
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 77
241000238876 Acari Species 0.000 claims description 17
239000004480 active ingredient Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
244000045947 parasite Species 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
241001465754 Metazoa Species 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
239000013543 active substance Substances 0.000 claims description 9
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 8
230000000895 acaricidal effect Effects 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
241000196324 Embryophyta Species 0.000 claims description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
239000000642 acaricide Substances 0.000 claims description 5
244000000054 animal parasite Species 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
239000002917 insecticide Substances 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 claims description 3
150000001298 alcohols Chemical class 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000005645 nematicide Substances 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
238000003975 animal breeding Methods 0.000 claims description 2
125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
QQHOVRKETYPQHY-UHFFFAOYSA-N 2-(hydroxymethyl)-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical compound O=C1N(CO)C(=O)C2=C1CCCC2 QQHOVRKETYPQHY-UHFFFAOYSA-N 0.000 claims 2
VNHCVSAJTOUUBK-UHFFFAOYSA-N 1-(2,2-dichloroethenyl)cyclopropane-1-carboxylic acid Chemical compound ClC(Cl)=CC1(C(=O)O)CC1 VNHCVSAJTOUUBK-UHFFFAOYSA-N 0.000 claims 1
OYDPVRNLLQZQFY-UHFFFAOYSA-N 2,2-dimethyl-3-[(2-oxothiolan-3-ylidene)methyl]cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C1C(=O)SCC1 OYDPVRNLLQZQFY-UHFFFAOYSA-N 0.000 claims 1
AJGDRDUWEWODJP-UHFFFAOYSA-N 2-(2,2-dibromoethenyl)-1,1-dimethylcyclopropane Chemical class CC1(C)CC1C=C(Br)Br AJGDRDUWEWODJP-UHFFFAOYSA-N 0.000 claims 1
235000007516 Chrysanthemum Nutrition 0.000 claims 1
244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000000249 desinfective effect Effects 0.000 claims 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
125000001174 sulfone group Chemical group 0.000 claims 1
125000003375 sulfoxide group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000843 powder Substances 0.000 description 12
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000002360 preparation method Methods 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000005292 vacuum distillation Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
230000003071 parasitic effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
238000001816 cooling Methods 0.000 description 4
230000001069 nematicidal effect Effects 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
241000255925 Diptera Species 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WXOMTJVVIMOXJL-BOBFKVMVSA-A O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O Chemical compound O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)O.O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O WXOMTJVVIMOXJL-BOBFKVMVSA-A 0.000 description 2
240000004460 Tanacetum coccineum Species 0.000 description 2
ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
230000000749 insecticidal effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
229960005235 piperonyl butoxide Drugs 0.000 description 2
229940015367 pyrethrum Drugs 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
DEUJSGDXBNTQMY-UHFFFAOYSA-N 1,2,2-trifluoroethanol Chemical compound OC(F)C(F)F DEUJSGDXBNTQMY-UHFFFAOYSA-N 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
235000017060 Arachis glabrata Nutrition 0.000 description 1
244000105624 Arachis hypogaea Species 0.000 description 1
235000010777 Arachis hypogaea Nutrition 0.000 description 1
235000018262 Arachis monticola Nutrition 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241000238678 Boophilus Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
RVTASIKGYRFQPD-UHFFFAOYSA-N CCCC(CC(C=C1)=CC2=C1OCO2)O.C1OC(C=CC=C2)=C2O1 Chemical compound CCCC(CC(C=C1)=CC2=C1OCO2)O.C1OC(C=CC=C2)=C2O1 RVTASIKGYRFQPD-UHFFFAOYSA-N 0.000 description 1
241000218645 Cedrus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
241000254173 Coleoptera Species 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
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
241000238631 Hexapoda Species 0.000 description 1
241000217776 Holocentridae Species 0.000 description 1
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
235000011613 Pinus brutia Nutrition 0.000 description 1
241000018646 Pinus brutia Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000443 aerosol Substances 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
230000009286 beneficial effect Effects 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000013329 compounding Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000020232 peanut Nutrition 0.000 description 1
BKDYPNZJRPEUEI-UHFFFAOYSA-N penta-1,4-diyn-3-ol Chemical compound C#CC(O)C#C BKDYPNZJRPEUEI-UHFFFAOYSA-N 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
CKFBFQHBUCDOHL-UHFFFAOYSA-N phenoxy(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)OC1=CC=CC=C1 CKFBFQHBUCDOHL-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000005507 spraying Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000005068 transpiration Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

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
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Polymers & Plastics (AREA)
Veterinary Medicine (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Pharmacology & Pharmacy (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Environmental Sciences (AREA)
Animal Husbandry (AREA)
Tropical Medicine & Parasitology (AREA)
Food Science & Technology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP60210355A 1984-09-26 1985-09-25 シクロプロパンカルボン酸とジアセチレンアルコ−ルとのエステル、それらの製造法、寄生虫の駆除への使用及びそれらを含む組成物 Pending JPS61275251A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8414774A FR2570698B1 (fr)	1984-09-26	1984-09-26	Esters d'acides cyclopropane carboxyliques et d'alcools diacetyleniques, leur procede de preparation et leur application a la lutte contre les parasites
FR8414774		1984-09-26

Publications (1)

Publication Number	Publication Date
JPS61275251A true JPS61275251A (ja)	1986-12-05

Family

ID=9308095

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60210355A Pending JPS61275251A (ja)	1984-09-26	1985-09-25	シクロプロパンカルボン酸とジアセチレンアルコ−ルとのエステル、それらの製造法、寄生虫の駆除への使用及びそれらを含む組成物

Country Status (7)

Country	Link
JP (1)	JPS61275251A (fr)
CH (1)	CH668065A5 (fr)
DE (1)	DE3534336A1 (fr)
FR (1)	FR2570698B1 (fr)
GB (1)	GB2164937B (fr)
IT (1)	IT1182875B (fr)
NL (1)	NL8502617A (fr)

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4003945A (en) *	1973-04-20	1977-01-18	Sumitomo Chemical Company, Limited	Novel cyclopropanecarboxylates
GB2099810A (en) *	1981-06-09	1982-12-15	Shell Int Research	Cyclopropanecarboxylate esters and their use as pesticides
FR2537973B1 (fr) *	1982-12-15	1985-11-08	Roussel Uclaf	Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant

1984
- 1984-09-26 FR FR8414774A patent/FR2570698B1/fr not_active Expired
1985
- 1985-09-25 JP JP60210355A patent/JPS61275251A/ja active Pending
- 1985-09-25 IT IT48589/85A patent/IT1182875B/it active
- 1985-09-25 GB GB08523602A patent/GB2164937B/en not_active Expired
- 1985-09-25 NL NL8502617A patent/NL8502617A/nl not_active Application Discontinuation
- 1985-09-25 CH CH4154/85A patent/CH668065A5/fr not_active IP Right Cessation
- 1985-09-26 DE DE19853534336 patent/DE3534336A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
FR2570698A1 (fr)	1986-03-28
IT8548589A0 (it)	1985-09-25
GB2164937A (en)	1986-04-03
CH668065A5 (fr)	1988-11-30
GB8523602D0 (en)	1985-10-30
NL8502617A (nl)	1986-04-16
GB2164937B (en)	1987-12-23
IT1182875B (it)	1987-10-05
FR2570698B1 (fr)	1986-12-19
DE3534336A1 (de)	1986-04-03

Publication	Publication Date	Title
JPS6176456A (ja)	1986-04-18	ピロ−ルの新誘導体、その製造法及び有害生物防除剤としての使用
JPH01156943A (ja)	1989-06-20	シクロプロパンカルボン酸の新誘導体
JPS63201146A (ja)	1988-08-19	ピレトリン酸と関連した新規なシクロプロパンカルボン酸エステル、その製造法及び害虫駆除への使用
JPS6224418B2 (fr)	1987-05-28
US4602038A (en)	1986-07-22	Insecticidal cyclopropane carboxylates
JPH05112519A (ja)	1993-05-07	３−［２−シアノ−２−ハロゲノエテニル−２，２−ジメチルシクロプロパンカルボン酸の新エステル誘導体、それらの製造法及び殺生物としての使用
JPH02233644A (ja)	1990-09-17	新規の２，２―ジメチル―３―（２―モノハロエテニル）シクロプロパンカルボン酸誘導体、それらの製造方法及び害虫駆除剤としてのそれらの使用
JPH02225442A (ja)	1990-09-07	３―エテニル―２，２―ジメチルシクロプロパンカルボン酸の新規な弗素化誘導体、その製造方法、害虫駆除剤としてのその使用及びそれを含有する組成物
JPH0723350B2 (ja)	1995-03-15	シクロプロパンカルボン酸の新誘導体、それらの製造法及びそれらを含有する寄生虫駆除用組成物
JPS63122661A (ja)	1988-05-26	シクロプロパンカルボン酸エステルの新エチレンオキシム誘導体、その製造方法及び中間体並びに寄生虫駆除への使用
CA1265808A (fr)	1990-02-13	Derives de l'acide cyclopropane carboxylique a substituant iode, leur preparation, leur application a la lutte contre les parasites des vegetaux et des animaux et les compositions les renfermant
JPS63152358A (ja)	1988-06-24	インドールの新誘導体、それらの製造法、それらの寄生虫駆除への使用及びそれらを含有する組成物
JPH0456817B2 (fr)	1992-09-09
JPS61275251A (ja)	1986-12-05	シクロプロパンカルボン酸とジアセチレンアルコ−ルとのエステル、それらの製造法、寄生虫の駆除への使用及びそれらを含む組成物
JPH05186423A (ja)	1993-07-27	１，３，４，５，６，７−ヘキサヒドロ−１，３−ジオキソ−２ｈ−イソインドール−２−イルメチルアルコールの新規なピレスリノイドエステル、それらの製造法及びそれらのペスチサイドとしての用途
DE69417969T2 (de)	1999-09-30	Von 6-Trifluoromethylbenzylalkohol abgeleitete Pyrethrinoidester, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide
JP3320453B2 (ja)	2002-09-03	４−アミノ−２，３，５，６−テトラフルオルフェニルメチルアルコールの新規なピレスリノイドエステル、それらの製造法及びそれらのペスチサイドとしての用途
FR2629452A1 (fr)	1989-10-06	Nouveau procede de preparation de derives trifluoromethylvinyliques a partir de derives halogenovinyliques correspondants
JPH0641015A (ja)	1994-02-15	６−（トリフルオルメチル）ベンジルアルコールから誘導される新規なピレスリノイドエステル、それらの製造法及びそれらの有害生物駆除剤としての用途
JPS5899460A (ja)	1983-06-13	アルキルチオカルボニル基を含むシクロプロパンカルボン酸の新誘導体、それらの製造法、植物、動物及び家屋の寄生虫の駆除への適用並びにそれらを含有する組成物
JPS5998055A (ja)	1984-06-06	アルキルチオカルボニル基とハロゲン原子を含有するシクロプロパンカルボン酸の新誘導体、それらの製造、植物、動物及び家屋の寄生虫の駆除への使用、それらを含む組成物
JPH0429668B2 (fr)	1992-05-19
JPH0339062B2 (fr)	1991-06-12
JPS59118742A (ja)	1984-07-09	シクロプロパンカルボン酸と不飽和脂肪族アルコールとのエステル、その製造法及びそれらを含む害虫駆除用組成物
JPS61200946A (ja)	1986-09-05	２，２‐ジメチル‐３‐エテニルシクロプロパンカルボン酸から得られる新エステル、それらの製造、それらの寄生虫駆除への使用及ぴそれらを含有する組成物