JPH05502896A - ４―（ジハロゲノメチル）―２，３，５，６―テトラフルオルベンジ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ペスチサイドとしての用途 - Google Patents

４―（ジハロゲノメチル）―２，３，５，６―テトラフルオルベンジ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ペスチサイドとしての用途

Info

Publication number: JPH05502896A
Authority: JP; Japan
Prior art keywords: compound; formula; group; alcohol; atom
Prior art date: 1990-10-02
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

JP3516430A

Other languages

English (en)

Japanese (ja)

Inventor

ブノワ，マルク

ドムート，ジャンピエール

ドマセ，ジャック

Original Assignee

ルセル　ユクラフ

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.)

1990-10-02

Filing date

1991-10-01

Publication date

1993-05-20

1991-10-01 Application filed by ルセル　ユクラフ filed Critical ルセル　ユクラフ

1993-05-20 Publication of JPH05502896A publication Critical patent/JPH05502896A/ja

Status Pending legal-status Critical Current

Links

150000002148 esters Chemical class 0.000 title claims description 8
238000004519 manufacturing process Methods 0.000 title claims description 8
239000000575 pesticide Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 88
239000000203 mixture Substances 0.000 claims description 37
125000004432 carbon atom Chemical group C* 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 20
239000004480 active ingredient Substances 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 16
239000000126 substance Substances 0.000 claims description 15
241000238876 Acari Species 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
244000045947 parasite Species 0.000 claims description 12
241000607479 Yersinia pestis Species 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
241001465754 Metazoa Species 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
241000196324 Embryophyta Species 0.000 claims description 9
230000000895 acaricidal effect Effects 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
125000000524 functional group Chemical group 0.000 claims description 9
239000000642 acaricide Substances 0.000 claims description 8
229910052801 chlorine Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
-1 compound Compound Chemical class 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 claims description 6
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
125000000304 alkynyl group Chemical group 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
239000002917 insecticide Substances 0.000 claims description 6
239000005645 nematicide Substances 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
241000238631 Hexapoda Species 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
239000004615 ingredient Substances 0.000 claims description 5
230000003071 parasitic effect Effects 0.000 claims description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
230000001069 nematicidal effect Effects 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003158 alcohol group Chemical group 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
244000000054 animal parasite Species 0.000 claims 2
240000007124 Brassica oleracea Species 0.000 claims 1
235000007516 Chrysanthemum Nutrition 0.000 claims 1
244000189548 Chrysanthemum x morifolium Species 0.000 claims 1
230000003213 activating effect Effects 0.000 claims 1
150000001555 benzenes Chemical class 0.000 claims 1
125000004980 cyclopropylene group Chemical group 0.000 claims 1
230000001568 sexual effect Effects 0.000 claims 1
239000000843 powder Substances 0.000 description 11
239000000243 solution Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000000034 method Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
241000132121 Acaridae Species 0.000 description 3
241000255925 Diptera Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
229960005235 piperonyl butoxide Drugs 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000000779 smoke Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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
241000255930 Chironomidae Species 0.000 description 2
241000257226 Muscidae Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
240000004460 Tanacetum coccineum Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
239000003905 agrochemical Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000008187 granular material Substances 0.000 description 2
MOTRZVVGCFFABN-UHFFFAOYSA-N hexane;2-propan-2-yloxypropane Chemical compound CCCCCC.CC(C)OC(C)C MOTRZVVGCFFABN-UHFFFAOYSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229940015367 pyrethrum Drugs 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
AGWVQASYTKCTCC-UHFFFAOYSA-N (2,3,5,6-tetrafluorophenyl)methanol Chemical compound OCC1=C(F)C(F)=CC(F)=C1F AGWVQASYTKCTCC-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
RVBUZBPJAGZHSQ-UHFFFAOYSA-N 2-chlorobutanoic acid Chemical compound CCC(Cl)C(O)=O RVBUZBPJAGZHSQ-UHFFFAOYSA-N 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])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
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
241001600407 Aphis <genus> Species 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
241000238678 Boophilus Species 0.000 description 1
VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
244000060011 Cocos nucifera Species 0.000 description 1
235000013162 Cocos nucifera Nutrition 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
241000489975 Diabrotica Species 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
241001427543 Elateridae Species 0.000 description 1
241000217776 Holocentridae Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000883290 Myriapoda Species 0.000 description 1
241000244206 Nematoda Species 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 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
240000008299 Pinus lambertiana Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
241000872198 Serjania polyphylla Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000219873 Vicia Species 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
238000000889 atomisation 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
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
229960001506 brilliant green Drugs 0.000 description 1
HXCILVUBKWANLN-UHFFFAOYSA-N brilliant green cation Chemical compound C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 HXCILVUBKWANLN-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
239000002316 fumigant Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
150000002366 halogen compounds Chemical class 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
238000010348 incorporation Methods 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
JKRHDMPWBFBQDZ-UHFFFAOYSA-N n'-hexylmethanediimine Chemical compound CCCCCCN=C=N JKRHDMPWBFBQDZ-UHFFFAOYSA-N 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
230000000422 nocturnal effect Effects 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 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
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011160 research Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
230000000391 smoking effect Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/31—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing rings other than six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/46—Halogenated unsaturated alcohols containing only six-membered aromatic rings as cyclic parts
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

JP3516430A 1990-10-02 1991-10-01 ４―（ジハロゲノメチル）―２，３，５，６―テトラフルオルベンジ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ペスチサイドとしての用途 Pending JPH05502896A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9012104A FR2667313B1 (fr)	1990-10-02	1990-10-02	Nouveaux esters pyrethrinouides de l'alcool 4-(difluoromethyl), 2,3,5,6-tetrafluorobenzylique, leur procede de preparation et leur application comme pesticides.
FR90/12104		1990-10-02

Publications (1)

Publication Number	Publication Date
JPH05502896A true JPH05502896A (ja)	1993-05-20

Family

ID=9400834

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3516430A Pending JPH05502896A (ja)	1990-10-02	1991-10-01	４―（ジハロゲノメチル）―２，３，５，６―テトラフルオルベンジ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ペスチサイドとしての用途

Country Status (4)

Country	Link
EP (1)	EP0502183A1 (fr)
JP (1)	JPH05502896A (fr)
FR (1)	FR2667313B1 (fr)
WO (1)	WO1992006065A1 (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0032121B1 (fr) *	1979-02-14	1984-05-16	Imperial Chemical Industries Plc	Tétrafluorobenzylalcools substitués et halogénures correspondants
GB8403548D0 (en) *	1984-02-10	1984-03-14	Ici Plc	Chemical process

1990
- 1990-10-02 FR FR9012104A patent/FR2667313B1/fr not_active Expired - Fee Related
1991
- 1991-10-01 WO PCT/FR1991/000769 patent/WO1992006065A1/fr not_active Ceased
- 1991-10-01 JP JP3516430A patent/JPH05502896A/ja active Pending
- 1991-10-01 EP EP91919212A patent/EP0502183A1/fr not_active Withdrawn

Also Published As

Publication number	Publication date
FR2667313A1 (fr)	1992-04-03
FR2667313B1 (fr)	1993-12-31
WO1992006065A1 (fr)	1992-04-16
EP0502183A1 (fr)	1992-09-09

Publication	Publication Date	Title
KR960005514B1 (ko)	1996-04-25	피레트르산에 관련된 시클로프로판카르복실산 에스테르, 이들의 제조방법 및 해충박멸을 위한 이들의 사용방법
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
JPS6224418B2 (fr)	1987-05-28
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
FR2687152A1 (fr)	1993-08-13	Nouveaux esters pyrethrinouides derives d'alcool furanique ou thiophenique, leur procede de preparation et leur application comme pesticides.
JPH0625196A (ja)	1994-02-01	チアゾール系アルコールから誘導される新規なピレスロイドエステル、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
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
JPH0692356B2 (ja)	1994-11-16	シアノ基を有するシクロプロパンカルボン酸のエステル，その製造法及びその殺虫殺ダニ剤としての使用
JP2007262076A (ja)	2007-10-11	２，２−ジメチル−３−（３，３，３−トリフルオル−１−プロペニル）シクロプロパンカルボン酸から誘導される新規のエステル、その製造方法及び害虫駆除剤としてのその使用
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
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
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
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
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
JPH0220634B2 (fr)	1990-05-10
DE69417969T2 (de)	1999-09-30	Von 6-Trifluoromethylbenzylalkohol abgeleitete Pyrethrinoidester, Verfahren zu ihrer Herstellung und ihre Anwendung als Pestizide
JPH05502896A (ja)	1993-05-20	４―（ジハロゲノメチル）―２，３，５，６―テトラフルオルベンジ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ペスチサイドとしての用途
JPH0456817B2 (fr)	1992-09-09
JPH04352746A (ja)	1992-12-07	新規の３−（３，３，３−トリフルオル−２−クロルプロペニル）−２，２−ジメチルシクロプロパンカルボン酸エステル、その製造方法及び害虫駆除剤としてのその使用
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
JPH0339062B2 (fr)	1991-06-12
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
JPH0625096A (ja)	1994-02-01	３位に１−ブテン−３−イニル鎖を有する２，２−ジメチル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の有害生物駆除剤としての用途
JPH0429668B2 (fr)	1992-05-19
JPH06507421A (ja)	1994-08-25	イソオキサゾール又はイソチアゾール系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使用