CA1254227A - Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides - Google Patents

Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides

Info

Publication number: CA1254227A
Authority: CA; Canada
Prior art keywords: carboxylate; dimethyl; alpha; cyanobenzyl; fluorophenoxy
Prior art date: 1977-07-06
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.): Expired

Application number

CA000440529A

Other languages

English (en)

Inventor

Rainer Fuchs

Ingeborg Hammann

Wilhelm Stendel

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.)

Bayer AG

Original Assignee

Bayer AG

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.)

1977-07-06

Filing date

1983-11-04

Publication date

1989-05-16

1977-07-06 Priority claimed from DE19772730515 external-priority patent/DE2730515A1/de

1983-11-04 Application filed by Bayer AG filed Critical Bayer AG

1983-11-04 Priority to CA000440529A priority Critical patent/CA1254227A/fr

1989-05-16 Application granted granted Critical

1989-05-16 Publication of CA1254227A publication Critical patent/CA1254227A/fr

Status Expired legal-status Critical Current

Links

-1 phenoxybenzyloxycarbonyl Chemical class 0.000 title claims abstract description 31
230000000895 acaricidal effect Effects 0.000 title abstract description 7
239000000642 acaricide Substances 0.000 title abstract description 3
239000002917 insecticide Substances 0.000 title abstract description 3
150000001875 compounds Chemical class 0.000 claims abstract description 64
239000001257 hydrogen Substances 0.000 claims abstract description 16
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims abstract description 10
241001465754 Metazoa Species 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
CKFBFQHBUCDOHL-UHFFFAOYSA-N phenoxy(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)OC1=CC=CC=C1 CKFBFQHBUCDOHL-UHFFFAOYSA-N 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 34
239000002253 acid Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 18
230000008569 process Effects 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 16
239000000460 chlorine Chemical group 0.000 claims description 14
150000007942 carboxylates Chemical class 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 13
229910052783 alkali metal Inorganic materials 0.000 claims description 9
241000607479 Yersinia pestis Species 0.000 claims description 8
241000238631 Hexapoda Species 0.000 claims description 7
241000238421 Arthropoda Species 0.000 claims description 6
150000003863 ammonium salts Chemical class 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
150000001340 alkali metals Chemical class 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Chemical group 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
150000001342 alkaline earth metals Chemical class 0.000 claims 3
150000001735 carboxylic acids Chemical class 0.000 claims 3
125000004093 cyano group Chemical group *C#N 0.000 claims 2
KXNJUSYYPCKFJZ-UHFFFAOYSA-N (3-phenoxyphenyl)methyl 3-ethenyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KXNJUSYYPCKFJZ-UHFFFAOYSA-N 0.000 claims 1
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
RLOOOVXMCQHJFE-UHFFFAOYSA-N 3-(2-chloro-2-phenylethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C(Cl)C1=CC=CC=C1 RLOOOVXMCQHJFE-UHFFFAOYSA-N 0.000 claims 1
OLKWYZYVQYPFIM-UHFFFAOYSA-N 3-[2-chloro-2-(4-chlorophenyl)ethenyl]-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=C(Cl)C1=CC=C(Cl)C=C1 OLKWYZYVQYPFIM-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 7
150000002825 nitriles Chemical class 0.000 abstract description 4
150000002431 hydrogen Chemical class 0.000 abstract description 3
230000002349 favourable effect Effects 0.000 abstract description 2
125000001424 substituent group Chemical group 0.000 abstract description 2
230000001988 toxicity Effects 0.000 abstract description 2
231100000419 toxicity Toxicity 0.000 abstract description 2
239000000575 pesticide Substances 0.000 abstract 1
229920002554 vinyl polymer Polymers 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 14
229960004217 benzyl alcohol Drugs 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
230000006378 damage Effects 0.000 description 9
238000009472 formulation Methods 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
229940073608 benzyl chloride Drugs 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
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241000196324 Embryophyta Species 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000370 acceptor Substances 0.000 description 5
125000002877 alkyl aryl group Chemical group 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000000243 solution Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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239000003795 chemical substances by application Substances 0.000 description 4
230000000875 corresponding effect Effects 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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238000009835 boiling Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
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239000012071 phase Substances 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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235000011303 Brassica alboglabra Nutrition 0.000 description 2
235000011302 Brassica oleracea Nutrition 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
241000721623 Myzus Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 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
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ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000238680 Rhipicephalus microplus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
241001454295 Tetranychidae Species 0.000 description 2
LDVNDECONPCEAK-UHFFFAOYSA-N [3-(4-fluorophenoxy)phenyl]methanol Chemical compound OCC1=CC=CC(OC=2C=CC(F)=CC=2)=C1 LDVNDECONPCEAK-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
210000002969 egg yolk Anatomy 0.000 description 2
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150000002170 ethers Chemical class 0.000 description 2
ZFZXRNVTYVRULM-UHFFFAOYSA-N ethyl 3-formyl-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CCOC(=O)C1C(C=O)C1(C)C ZFZXRNVTYVRULM-UHFFFAOYSA-N 0.000 description 2
LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical class CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 1
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UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 description 1
ATJWZOMSCCNRQJ-UHFFFAOYSA-N 1-(chloromethyl)-3-(2-fluorophenoxy)benzene Chemical compound FC1=CC=CC=C1OC1=CC=CC(CCl)=C1 ATJWZOMSCCNRQJ-UHFFFAOYSA-N 0.000 description 1
GBEWQUUEYQQXIJ-UHFFFAOYSA-N 1-(chloromethyl)-3-(3-fluorophenoxy)benzene Chemical compound FC1=CC=CC(OC=2C=C(CCl)C=CC=2)=C1 GBEWQUUEYQQXIJ-UHFFFAOYSA-N 0.000 description 1
BWXBCFLXICBJEH-UHFFFAOYSA-N 1-(chloromethyl)-3-(4-fluorophenoxy)benzene Chemical compound C1=CC(F)=CC=C1OC1=CC=CC(CCl)=C1 BWXBCFLXICBJEH-UHFFFAOYSA-N 0.000 description 1
QUYVTGFWFHQVRO-UHFFFAOYSA-N 1-(chloromethyl)-3-phenoxybenzene Chemical compound ClCC1=CC=CC(OC=2C=CC=CC=2)=C1 QUYVTGFWFHQVRO-UHFFFAOYSA-N 0.000 description 1
IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
BVQPVBZRJSFOEZ-UHFFFAOYSA-N 1-chloro-4-(diethoxyphosphorylmethyl)benzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(Cl)C=C1 BVQPVBZRJSFOEZ-UHFFFAOYSA-N 0.000 description 1
DVJZQSVZKJOQEW-UHFFFAOYSA-N 2,2-dimethyl-3-(2-phenylethenyl)cyclopropane-1-carbonyl chloride Chemical compound ClC(=O)C1C(C)(C)C1C=CC1=CC=CC=C1 DVJZQSVZKJOQEW-UHFFFAOYSA-N 0.000 description 1
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Agricultural Chemicals And Associated Chemicals (AREA)

CA000440529A 1977-07-06 1983-11-04 Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides Expired CA1254227A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000440529A CA1254227A (fr)	1977-07-06	1983-11-04	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19772730515 DE2730515A1 (de)	1977-07-06	1977-07-06	Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DEP2730515.3		1977-07-06
CA 306758 CA1254227C (fr)	1977-07-06	1978-07-04	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides
CA000440529A CA1254227A (fr)	1977-07-06	1983-11-04	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides

Publications (1)

Publication Number	Publication Date
CA1254227A true CA1254227A (fr)	1989-05-16

Family

ID=25668727

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000440529A Expired CA1254227A (fr)	1977-07-06	1983-11-04	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides

Country Status (1)

Country	Link
CA (1)	CA1254227A (fr)

1983
- 1983-11-04 CA CA000440529A patent/CA1254227A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-05-16	MKEX	Expiry

Publication	Publication Date	Title
CA1254227C (fr)	1989-05-16	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides
CA1113477A (fr)	1981-12-01	Derives de phenoxybenzyloxycarbonyle substitues, et leur utilisation comme insecticides et acaricides
CA1129434A (fr)	1982-08-10	Esters d'acides cyclopropanecarboxyliques et de benzyalcools halogenes; emploi comme pesticides
US4485252A (en)	1984-11-27	2-Phenyl-alk-1-enyl-cyclopropane-carboxylic acid intermediates
US4271186A (en)	1981-06-02	Stilbene compounds and insecticidal/acaricidal compositions
US4199596A (en)	1980-04-22	Combating arthropods with fluorine-substituted phenoxybenzylcarbonyl derivatives
US4423066A (en)	1983-12-27	Combating arthropods with perfluorobenzyl 2,2-dimethyl-3-vinyl-cyclopropane carboxylates
US4287208A (en)	1981-09-01	Combating arthropods with stereoisomers of 2,2-dimethyl-3-(2,2-dichlorovinyl)-cyclopropane-1-carboxylic acid α-c
CA1156254A (fr)	1983-11-01	4-fluoro-3-phenoxy-benzyl 3-alkene-1-yl-2,3- dimethyl-cyclopropanecarboxylates, procede de preparation et application dans la lutte contre les animaux nuisibles
US4360690A (en)	1982-11-23	Combating pests with 1-aryl-cyclopropane-1-carboxylic acid esters
US4388322A (en)	1983-06-14	Combating pests with substituted 3-(1,2-dibromo-alkyl)-2,2-dimethyl-cyclopropane-1-carboxylic acid esters
EP0004902B1 (fr)	1982-04-21	Dérivés de benzodioxolanes, procédé pour leur préparation et leur utilisation comme synergistes de pesticides
CA1222525A (fr)	1987-06-02	Derives fluores d'esters benzyliques de l'acide 2,2,3,3-tetramethyl-cyclopropane-1-carboxylique, procede de preparation et utilisation dans les insecticides et acaricides
US4350640A (en)	1982-09-21	Preparation of substituted (cyclo)alkanecarboxylic acid α-cyano-3-phenoxy-benzyl esters
US4054650A (en)	1977-10-18	O,O-Diethyl-O-[N-methoxy-2-nitrobenzimidoyl]-thiono-phosphoric acid esters
US4250187A (en)	1981-02-10	4,5-Dichloro-3-organo-1,2-methylenedioxy-benzene arthropodicide synergizing agents
US4279920A (en)	1981-07-21	2,2-Dimethyl-3-(2-bromo-2-phenyl-vinyl)-cyclopropanecarboxylic acid 3-phenoxybenzyl esters and pesticidal use
US4254113A (en)	1981-03-03	Combating arthropods with O-Alkyl-O-(2-cyclopropyl-6-methyl-pyrimidin-4-yl)-thionophosphonic acid esters
US4344960A (en)	1982-08-17	Combating insects and acarids with 3-(2-chloro-3,3,4,4,4-pentafluoro-1-butenyl)-2,2-dimethyl-cyclopropanecarboxylic acid esters
CA1151666A (fr)	1983-08-09	Fluoro-benzyl esters d'acide 3-(2,3-dichloro-3,3-difluoro-prop-1-en-1-yl)-2,2 dimethyl-cyclo-propane carboxylique; procede pour les preparer et leur utilisation dans des pesticides
US4297366A (en)	1981-10-27	Combating arthropods with 2,2-dimethyl-3-(2-fluoroalkyl-2-oxy-vinyl)-cyclopropane-carboxylic acid esters
CA1254227A (fr)	1989-05-16	Derives phenoxybenzyloxycarbonyl substitues et leurs applications comme insecticides et acaricides
CA1162925A (fr)	1984-02-28	Esters phenoxypyridylmethyliques, methode pour les preparer, et utilisation comme pesticides
EP0057384A2 (fr)	1982-08-11	Esters 4-fluoro-3-halophénoxy benzyles, procédé pour leur fabrication et leur utilisation en pesticides ainsi que produits intermédiaires et procédé pour leur préparation
JPS6320423B2 (fr)	1988-04-27