JPS6113459B2 - - Google Patents

Info

Publication number: JPS6113459B2
Authority: JP; Japan
Prior art keywords: formula; hydrogen atom; represented; parts; compound according
Prior art date: 1976-02-17
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

JP52016635A

Other languages

English (en)

Japanese (ja)

Other versions

JPS52100455A (en

Inventor

Dorabetsuku Yoozefu

Fuaruuku Sareemu

Guzeru Raurentsu

Kurisuchiansen Otsudo

Meiyaa Uirii

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.)

Novartis AG

Original Assignee

Ciba Geigy 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.)

1976-02-17

Filing date

1977-02-17

Publication date

1986-04-14

1976-02-17 Priority claimed from CH191076A external-priority patent/CH602005A5/de

1977-02-17 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1977-08-23 Publication of JPS52100455A publication Critical patent/JPS52100455A/ja

1986-04-14 Publication of JPS6113459B2 publication Critical patent/JPS6113459B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 29
239000004480 active ingredient Substances 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 11
230000000895 acaricidal effect Effects 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
-1 cyclopropanecarboxylic acid ester Chemical class 0.000 claims description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000000642 acaricide Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000002917 insecticide Substances 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
239000002253 acid Substances 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
239000000203 mixture Substances 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
230000000749 insecticidal effect Effects 0.000 description 8
238000000034 method Methods 0.000 description 8
239000000843 powder Substances 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000839 emulsion Substances 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
241001454293 Tetranychus urticae Species 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001327638 Cimex lectularius Species 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
239000000654 additive Substances 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
150000002191 fatty alcohols Chemical class 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
241000253994 Acyrthosiphon pisum Species 0.000 description 2
206010004194 Bed bug infestation Diseases 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000256257 Heliothis Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
241000238814 Orthoptera Species 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
241000256248 Spodoptera Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
240000006677 Vicia faba Species 0.000 description 2
235000010749 Vicia faba Nutrition 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000003380 propellant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UXPPDBVMSPAPCL-UHFFFAOYSA-N 1-prop-1-ynoxyprop-1-yne Chemical compound CC#COC#CC UXPPDBVMSPAPCL-UHFFFAOYSA-N 0.000 description 1
HRQBQVOUHQTQFJ-UHFFFAOYSA-N 2,2-dimethyl-3-(2-phenylethenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)C1C(C)(C)C1C=CC1=CC=CC=C1 HRQBQVOUHQTQFJ-UHFFFAOYSA-N 0.000 description 1
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 1
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 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241001143309 Acanthoscelides obtectus Species 0.000 description 1
241000238876 Acari Species 0.000 description 1
241000132121 Acaridae Species 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241001674044 Blattodea Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
241001498622 Cixius wagneri Species 0.000 description 1
241000255749 Coccinellidae Species 0.000 description 1
241001465977 Coccoidea Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000255925 Diptera Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
241000237365 Helicidae Species 0.000 description 1
241000256244 Heliothis virescens Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000258915 Leptinotarsa Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000257229 Musca <genus> Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
241000721621 Myzus persicae Species 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
244000141353 Prunus domestica Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000256250 Spodoptera littoralis Species 0.000 description 1
235000002098 Vicia faba var. major Nutrition 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000004649 carbonic 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
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
239000004491 dispersible concentrate Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
231100000487 gastrotoxic Toxicity 0.000 description 1
230000002162 gastrotoxic effect Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
235000021332 kidney beans Nutrition 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
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 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002903 organophosphorus compounds Chemical class 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
OSOBRNLAUDAQKA-UHFFFAOYSA-N prop-1-ynyl dihydrogen phosphate Chemical compound CC#COP(O)(O)=O OSOBRNLAUDAQKA-UHFFFAOYSA-N 0.000 description 1
VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical class CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
244000045561 useful plants Species 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP1663577A 1976-02-17 1977-02-17 Cyclopropane carboxylate ester process for preparing same and harmful living controlling agent containing same Granted JPS52100455A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH191076A CH602005A5 (en)	1976-02-17	1976-02-17	(3)-Phenoxy-benzyl styryl-cyclopropane carboxylates
CH5977		1977-01-04

Publications (2)

Publication Number	Publication Date
JPS52100455A JPS52100455A (en)	1977-08-23
JPS6113459B2 true JPS6113459B2 (da)	1986-04-14

Family

ID=25683390

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1663577A Granted JPS52100455A (en)	1976-02-17	1977-02-17	Cyclopropane carboxylate ester process for preparing same and harmful living controlling agent containing same

Country Status (8)

Country	Link
JP (1)	JPS52100455A (da)
DE (1)	DE2706184A1 (da)
FR (1)	FR2341554A1 (da)
GB (1)	GB1570928A (da)
IL (1)	IL51466A (da)
IT (1)	IT1076892B (da)
NL (1)	NL7701321A (da)
OA (1)	OA05647A (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1260486A (en) *	1976-08-27	1989-09-26	John F. Engel	Insecticidal styryl- and substituted- styrylcyclopropanecarboxylates
DE2730515A1 (de) *	1977-07-06	1979-01-18	Bayer Ag	Substituierte phenoxybenzyloxycarbonylderivate, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide
DE2842542A1 (de) *	1978-09-29	1980-04-17	Bayer Ag	Substituierte bromostyryl-cyclopropancarbonsaeurephenoxybenzylester, verfahren zu ihrer herstellunnd ihre verwendung als insektizide und akarizide
JPS55129507U (da) *	1979-03-05	1980-09-12
DE2916321A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von styryl- cyclopropan-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916357A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von 3-(2-aryl-vinyl)-2,2-dimethyl-cyclopropan-1-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916417A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von 3-(aryl- vinyl)-2,2-dimethyl-cyclopropan-1-carbonsaeureestern und neue zwischenprodukte dafuer
DE2916358A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Substituierte styrylcyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
DE2916375A1 (de) *	1979-04-23	1980-11-06	Bayer Ag	Verfahren zur herstellung von styryl-cyclopropan-carbonsaeureestern und neue zwischenprodukte dafuer
DE2920947A1 (de) *	1979-05-23	1980-12-04	Bayer Ag	2-phenyl-alken-1-yl-cyclopropan- carbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide und zwischenprodukte zu ihrer herstellung

1977
- 1977-02-08 NL NL7701321A patent/NL7701321A/xx not_active Application Discontinuation
- 1977-02-14 DE DE19772706184 patent/DE2706184A1/de not_active Ceased
- 1977-02-15 FR FR7704227A patent/FR2341554A1/fr active Granted
- 1977-02-16 IL IL51466A patent/IL51466A/xx unknown
- 1977-02-16 GB GB6501/77A patent/GB1570928A/en not_active Expired
- 1977-02-16 IT IT20351/77A patent/IT1076892B/it active
- 1977-02-17 JP JP1663577A patent/JPS52100455A/ja active Granted
- 1977-04-27 OA OA56153A patent/OA05647A/xx unknown

Also Published As

Publication number	Publication date
IL51466A (en)	1979-09-30
IL51466A0 (en)	1977-04-29
DE2706184A1 (de)	1977-08-18
FR2341554B1 (da)	1980-02-08
FR2341554A1 (fr)	1977-09-16
JPS52100455A (en)	1977-08-23
IT1076892B (it)	1985-04-27
NL7701321A (nl)	1977-08-19
GB1570928A (en)	1980-07-09
OA05647A (fr)	1981-04-30

Publication	Publication Date	Title
HU184360B (en)	1984-08-28	Insecticide compositions containing halogenated cyclopropane-carboxylic acid esters and process for preparing the active substances
GB2097384A (en)	1982-11-03	Fluorinated benzyl esters of tetramethylcyclopropane carboxylic acid
US4607051A (en)	1986-08-19	Carbamic acid compound and use as a pesticide
JPS6113459B2 (da)	1986-04-14
JPH0124779B2 (da)	1989-05-15
CA1152092A (en)	1983-08-16	Pesticidal phenoxybenzyl cyclopropanecarboxylate derivatives
CA1132603A (en)	1982-09-28	Pesticidal phenoxybenzyl cyclopropanecarboxylate derivatives
US4161535A (en)	1979-07-17	Pesticidal 2-isopropyl-4-phenyl-3-butenoic acid benzyl esters
DE2731033A1 (de)	1978-01-26	2,2-dimethyl-3-isobutylcyclopropansaeureester
GB1587352A (en)	1981-04-01	Cyclopropanecarboxylic acid esters
US5420159A (en)	1995-05-30	Pyrethrinoid esters
GB1596903A (en)	1981-09-03	Insecticidal and acaricidal phenyl alkanoic acid esters
JP2809280B2 (ja)	1998-10-08	新規なイミデート殺虫剤
CA1129435A (en)	1982-08-10	CYCLOPROPANECARBOXYLIC ACID-PHENOXY-.alpha.-VINYL-BENZYL ESTERS, PROCESSES FOR PRODUCING THEM, AND THEIR USE IN COMBATING PESTS
US4219564A (en)	1980-08-26	Vinylcyclopropanecarboxylic acid-3-phenoxy-α-vinylbenzyl esters, processes for producing them, and their use in combating pests
US4625048A (en)	1986-11-25	Carbamic acid esters
JPS6030301B2 (ja)	1985-07-16	シクロプロパンカルボン酸３−（２，２−ジクロロビニルオキシ）ベンジルエステル、その製造方法及び該化合物を含有する殺虫、殺ダニ剤
FR2463118A1 (fr)	1981-02-20	Esters d'acides dihalogenovinylcyclopropane-carboxyliques, procedes pour leur preparation, leur utilisation en tant que pesticides, et alcools alpha-halogenoethynyl-3-phenoxy-benzyliques en tant que produits intermediaires de leur preparation
US4336266A (en)	1982-06-22	Insecticidal 2,2-dimethyl-3-(2',2'-dihalovinyl)-cyclopropane carboxylic acid 3-halophenoxy-α-vinylbenzyl esters
CA1092145A (en)	1980-12-23	Pesticidal metaphenoxybenzylcyclopropane carboxylate derivatives
US4782087A (en)	1988-11-01	Insecticidal prop-1-ynyl-3-phenoxybenzyl-2,2-dimethyl-3-(2,2-dihalovinyl)-cyclopropane-1-carboxylates
US4902697A (en)	1990-02-20	Derivatives of 2,2-dimethyl-cyclopropanecarboxylic acid
US4358459A (en)	1982-11-09	Cyclopropane carboxylic acid and process for their production and use
EP0008867B1 (en)	1983-04-13	Cyanovinyl pyrethroids, processes for the preparation of these compounds and pesticidal use of the cyanovinyl pyrethroids
HU193704B (en)	1987-11-30	Insecticide and acaricide compositions containing halogeno-benzyl-esters as active agents and process for producing the active agents