CH655302A5 - Esters d'alcools aromatiques ou heteroaromatiques, leur procede et moyens de mise en oeuvre du procede, leur utilisation dans la lutte contre les ectoparasites et les compositions les renfermant. - Google Patents

Esters d'alcools aromatiques ou heteroaromatiques, leur procede et moyens de mise en oeuvre du procede, leur utilisation dans la lutte contre les ectoparasites et les compositions les renfermant. Download PDF

Info

Publication number: CH655302A5
Authority: CH; Switzerland
Prior art keywords: radical; formula; alcohol; compounds; atom
Prior art date: 1981-10-23

Application number

CH6165/82A

Other languages

English (en)

French (fr)

Inventor

Jean Tessier

Jean-Pierre Demoute

Original Assignee

Roussel Uclaf

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.)

1981-10-23

Filing date

1982-10-22

Publication date

1986-04-15

1982-10-22 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1986-04-15 Publication of CH655302A5 publication Critical patent/CH655302A5/fr

Links

239000000203 mixture Substances 0.000 title claims description 54
238000000034 method Methods 0.000 title claims description 32
150000001298 alcohols Chemical class 0.000 title claims description 17
244000078703 ectoparasite Species 0.000 title claims description 3
-1 heteroaromatic radical Chemical class 0.000 claims description 73
150000001875 compounds Chemical class 0.000 claims description 63
125000005843 halogen group Chemical group 0.000 claims description 28
150000003254 radicals Chemical class 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 26
239000002253 acid Substances 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 11
229910052731 fluorine Inorganic materials 0.000 claims description 11
244000045947 parasite Species 0.000 claims description 9
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical class OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
230000000895 acaricidal effect Effects 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
239000000642 acaricide Substances 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
230000000749 insecticidal effect Effects 0.000 claims description 6
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
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 5
150000001555 benzenes Chemical class 0.000 claims description 5
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
239000011149 active material Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
230000001069 nematicidal effect Effects 0.000 claims description 3
239000002728 pyrethroid Substances 0.000 claims description 3
125000001174 sulfone group Chemical group 0.000 claims description 3
125000003375 sulfoxide group Chemical group 0.000 claims description 3
VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical class CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 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 description 2
241000039077 Copula Species 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
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 claims 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 claims 1
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 1
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 58
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
239000000243 solution Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
101150041968 CDC13 gene Proteins 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
238000004458 analytical method Methods 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000000377 silicon dioxide Substances 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
241000238876 Acari Species 0.000 description 9
241000238631 Hexapoda Species 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000003208 petroleum Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
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 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
238000003756 stirring Methods 0.000 description 7
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
230000003071 parasitic effect Effects 0.000 description 6
241000257226 Muscidae Species 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
241000238657 Blattella germanica Species 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003638 chemical reducing agent Substances 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
206010063409 Acarodermatitis Diseases 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
241000255925 Diptera Species 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
206010039509 Scab Diseases 0.000 description 3
241000447727 Scabies Species 0.000 description 3
230000032050 esterification Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229960005235 piperonyl butoxide Drugs 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
208000005687 scabies Diseases 0.000 description 3
DPZZOBZIZRBXFQ-NJGYIYPDSA-N (1r,3r)-3-(2,2-difluoroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)[C@@H](C=C(F)F)[C@H]1C(O)=O DPZZOBZIZRBXFQ-NJGYIYPDSA-N 0.000 description 2
VBNQMVZJHJDIKD-ZJUUUORDSA-N (1r,3r)-3-(cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@H]1C(C)(C)[C@@H]1C=C1CCCC1 VBNQMVZJHJDIKD-ZJUUUORDSA-N 0.000 description 2
FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241001481703 Rhipicephalus <genus> Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
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239000007864 aqueous solution Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
230000001680 brushing effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
MDIQXIJPQWLFSD-NJGYIYPDSA-N cis-3-(2,2-dibromovinyl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(O)=O MDIQXIJPQWLFSD-NJGYIYPDSA-N 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
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229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
239000008240 homogeneous mixture Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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235000010755 mineral Nutrition 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
230000000050 nutritive effect Effects 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
229920000053 polysorbate 80 Polymers 0.000 description 2
235000003270 potassium fluoride Nutrition 0.000 description 2
239000011698 potassium fluoride Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
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241000894007 species Species 0.000 description 2
239000000725 suspension Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
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230000000699 topical effect Effects 0.000 description 2
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 2
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125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
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CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
235000019728 animal nutrition Nutrition 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005129 aryl carbonyl group Chemical group 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000005110 aryl thio group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000002585 base Substances 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
239000003139 biocide Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
229960001506 brilliant green Drugs 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229950005228 bromoform Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
230000001079 digestive effect Effects 0.000 description 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000010410 dusting Methods 0.000 description 1
LBKYKBFMRILRCT-UHFFFAOYSA-N ethyl 3-phenoxybenzoate Chemical compound CCOC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 LBKYKBFMRILRCT-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000004467 fishmeal Substances 0.000 description 1
238000003197 gene knockdown Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 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
230000000361 pesticidal effect Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
239000004540 pour-on Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
238000000746 purification Methods 0.000 description 1
229940015367 pyrethrum Drugs 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000779 smoke Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 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
239000007921 spray Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Emergency Medicine (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH6165/82A 1981-10-23 1982-10-22 Esters d'alcools aromatiques ou heteroaromatiques, leur procede et moyens de mise en oeuvre du procede, leur utilisation dans la lutte contre les ectoparasites et les compositions les renfermant. CH655302A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8119944A FR2515176A1 (fr)	1981-10-23	1981-10-23	Nouveaux esters d'alcools aromatiques ou heteroaromatiques, leur procede de preparation et leur application a la lutte contre les parasites

Publications (1)

Publication Number	Publication Date
CH655302A5 true CH655302A5 (fr)	1986-04-15

Family

ID=9263335

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH6165/82A CH655302A5 (fr)	1981-10-23	1982-10-22	Esters d'alcools aromatiques ou heteroaromatiques, leur procede et moyens de mise en oeuvre du procede, leur utilisation dans la lutte contre les ectoparasites et les compositions les renfermant.

Country Status (7)

Country	Link
JP (1)	JPS5879955A (nl)
CH (1)	CH655302A5 (nl)
DE (1)	DE3239200A1 (nl)
FR (1)	FR2515176A1 (nl)
GB (1)	GB2108123A (nl)
IT (1)	IT1158023B (nl)
NL (1)	NL8204049A (nl)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4694013A (en) *	1985-11-08	1987-09-15	E. I. Du Pont De Nemours And Company	Insecticidal and acaricidal phenoxypyrdinyl esters and intermediates
GB8617649D0 (en) *	1986-07-18	1986-08-28	Ici Plc	Fluorobenzyl esters

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4152455A (en) *	1977-02-02	1979-05-01	Fmc Corporation	Insecticidal α-trifluoromethyl-3-phenoxybenzyl carboxylates
US4431668A (en) *	1977-12-01	1984-02-14	Dainippon Jochugiku Kabushiki Kaisha	Cyclopropane carboxylic acid ester derivatives
IN150399B (nl) *	1978-01-20	1982-09-25	Fmc Corp
US4200644A (en) *	1978-01-26	1980-04-29	Fmc Corporation	Arylthiovinylcyclopropanecarboxylate insecticides
JPS5581836A (en) *	1978-12-13	1980-06-20	Yoshio Katsuta	Derivative of cyclopropanecarboxylic acid ester, its preparation and insecticide containing the same
JPS5620547A (en) *	1979-07-31	1981-02-26	Yoshio Katsuta	Cyclopropanecarboxylic ester derivative, its preparation, and insecticide comprising the same
JPS5646843A (en) *	1979-09-23	1981-04-28	Yoshio Katsuta	Novel carboxylic acid ester derivative, preparation of novel carboxylic acid ester derivative, and insecticide containing novel carboxylic acid ester derivative
JPS56115741A (en) *	1980-02-16	1981-09-11	Yoshio Katsuta	Cyclopropanecarboxylic acid ester derivative, preparation of cyclopropanecarboxylic acid ester derivative, and insecticide containing cyclopropanecarboxylic acid ester derivative

1981
- 1981-10-23 FR FR8119944A patent/FR2515176A1/fr active Granted
1982
- 1982-10-20 NL NL8204049A patent/NL8204049A/nl not_active Application Discontinuation
- 1982-10-22 IT IT49340/82A patent/IT1158023B/it active
- 1982-10-22 DE DE19823239200 patent/DE3239200A1/de not_active Withdrawn
- 1982-10-22 JP JP57184813A patent/JPS5879955A/ja active Pending
- 1982-10-22 GB GB08230153A patent/GB2108123A/en not_active Withdrawn
- 1982-10-22 CH CH6165/82A patent/CH655302A5/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2108123A (en)	1983-05-11
FR2515176A1 (fr)	1983-04-29
NL8204049A (nl)	1983-05-16
IT1158023B (it)	1987-02-18
IT8249340A0 (it)	1982-10-22
JPS5879955A (ja)	1983-05-13
FR2515176B1 (nl)	1984-09-28
DE3239200A1 (de)	1983-05-11

Legal Events

Date	Code	Title	Description
1987-06-30	PL	Patent ceased

Publication	Publication Date	Title
EP0050534B1 (fr)	1985-04-03	Esters d'acides cyclopropane carboxyliques apparentés à l'acide pyréthrique, leur procédé de préparation et leur application à la lutte contre les parasites
EP0041021B1 (fr)	1984-07-25	Nouveaux dérivés de l'acide cyclopropane carboxylique, leur préparation, leur application à la lutte contre les parasites des végétaux et des animaux, les compositions les renfermant et les nouveaux intermédiaires obtenus
CA1325013C (fr)	1993-12-07	Esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
FR2580637A2 (fr)	1986-10-24	Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides
EP0448427B1 (fr)	1995-01-11	Nouveaux esters dérivés d'acide 3-[2-cyano 2-halogéno éthényl], 2,2-diméthyl cyclopropanecarboxylique,leur procédé de préparation et leur application comme pesticides
FR2642421A1 (fr)	1990-08-03	Nouveaux derives de l'acide 2,2-dimethyl 3-(2-monohaloethenyl) cyclopropane carboxylique, leur procede de preparation et leur application comme medicaments
EP0133406B1 (fr)	1987-04-22	Nouveaux dérivés de l'acide cyclopropane carboxylique, leur préparation, leur application à la lutte contre les parasites et les compositions les renfermant
EP0018894B1 (fr)	1982-02-17	Esters de dérivés de l'alléthrolone et d'acides carboxyliques, leur procédé de préparation et les compositions les renfermant
CA1237143A (fr)	1988-05-24	Cyclopropane carboxylates a structure allenique, leur procede et leurs intermediaires de preparation, leur application a la lutte contre les parasites et les compositions les renfermant
EP0267105B1 (fr)	1992-08-12	Nouvelles oximes éthyléniques dérivés d'esters de l'acide cyclopropane carboxylique, leur procédé et les intermédiaires de préparation et leur application à la lutte contre les parasites
CH638179A5 (fr)	1983-09-15	Esters d'acides cyclopropane carboxyliques portant une chaine chloree ou bromee, procede de preparation et compositions insecticides.
EP0557192B1 (fr)	1996-08-21	Esters pyréthrinoides, dérivés de l'alcool 6-(trifluorométhyl)benzylique, leur procédé de préparation et leur application comme pesticides
CA1239931A (fr)	1988-08-02	Esters derives d'acides 2,2-dimethyl cyclopropane carboxyliques et d'alcools biaryliques, leur procede de preparation, leur application a la lutte contre les parasites et les compositions les renfermant
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
EP0476708B1 (fr)	1995-11-08	Dérivés pyréthrinoides trifluorométhyl vinyliques, leur procédé de préparation, les intermédiaires de ce procédé et leur application à titre de pesticides
FR2474488A1 (fr)	1981-07-31	Derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites des vegetaux et des animaux a sang chaud
CH655302A5 (fr)	1986-04-15	Esters d'alcools aromatiques ou heteroaromatiques, leur procede et moyens de mise en oeuvre du procede, leur utilisation dans la lutte contre les ectoparasites et les compositions les renfermant.
FR2682382A1 (fr)	1993-04-16	Nouveaux derives de l'acide 1-naphtalene acetique, leur procede de preparation et leur application comme pesticides.
EP0498724B1 (fr)	1996-05-15	Nouveaux esters de l'acide 3-(3,3,3-trifluoro 2-chloropropényl) 2,2-diméthyl cyclopropanecarboxylique, leur procédé de préparation et leur application comme pesticides
FR2604173A1 (fr)	1988-03-25	Nouveaux derives de l'indole, leur procede de preparation et leur application comme pesticide
EP0007255A1 (fr)	1980-01-23	Esters d'acides cyclopropane carboxyliques substitués d'alcool alpha-cyané, leur procédé de préparation, les compositions pesticides les renfermant ainsi que leur application à titre de médicaments à usage vétérinaire
EP0445004B1 (fr)	1994-10-05	Dérivés du pyrrole, leur procédé de préparation et leur application comme pesticides
FR2687665A1 (fr)	1993-08-27	Nouveaux derives de l'acide 2,2-dimethyl cyclopropane-carboxylique portant en 3 une chaine but-1-en-3-ynyle, leur procede de preparation et leur application comme pesticides.
CH660188A5 (fr)	1987-03-31	Esters de n-methyl hydantoines d'acides cyclopropane carboxyliques, leur preparation et les compositions les renfermant.
FR2612184A1 (fr)	1988-09-16	Nouveaux derives du pyrrole substitues par un radical trifluoromethyle, leur procede de preparation et leur application comme pesticides