CH600771A5 - Dichlorovinyloxy-benzyl-cyclopropane-carboxylates - Google Patents

Dichlorovinyloxy-benzyl-cyclopropane-carboxylates

Info

Publication number: CH600771A5
Authority: CH; Switzerland
Prior art keywords: sep; formula; compound; parts; dichlorovinyloxy
Prior art date: 1975-07-28

Application number

CH985975A

Other languages

German (de)

English (en)

Inventor

Willy Meyer

Saleem Dr Farooq

Friedrich Dr Karrer

Jozef Dr Drabek

Laurenz Dr Gsell

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.)

1975-07-28

Filing date

1975-07-28

Publication date

1978-06-30

1975-07-28 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-07-28 Priority to CH985975A priority Critical patent/CH600771A5/de

1976-07-15 Priority to SU762381704A priority patent/SU649295A3/ru

1976-07-20 Priority to FR7622119A priority patent/FR2319622A1/fr

1976-07-20 Priority to US05/707,136 priority patent/US4291056A/en

1976-07-26 Priority to CA000257815A priority patent/CA1171428A/fr

1976-07-26 Priority to DE19762633551 priority patent/DE2633551A1/de

1976-07-27 Priority to IL50136A priority patent/IL50136A0/xx

1976-07-27 Priority to IT25752/76A priority patent/IT1062142B/it

1976-07-27 Priority to GB31268/76A priority patent/GB1561064A/en

1976-07-27 Priority to BE169258A priority patent/BE844541A/fr

1976-07-28 Priority to NL7608375A priority patent/NL7608375A/xx

1976-07-28 Priority to JP51090130A priority patent/JPS6030301B2/ja

1978-06-30 Publication of CH600771A5 publication Critical patent/CH600771A5/de

Links

CKHJAKHKIIUAAZ-UHFFFAOYSA-N OC(C(CC1=CC=CC=C1)(C1)C1OC=C(Cl)Cl)=O Chemical class OC(C(CC1=CC=CC=C1)(C1)C1OC=C(Cl)Cl)=O CKHJAKHKIIUAAZ-UHFFFAOYSA-N 0.000 title abstract 2
230000000749 insecticidal effect Effects 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
239000004480 active ingredient Substances 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
239000000243 solution Substances 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
-1 3- (2,2-dichlorovinyloxy) benzaldehyde cyanohydride Chemical compound 0.000 claims description 8
239000000839 emulsion Substances 0.000 claims description 8
238000012360 testing method Methods 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
WIMOGUTUZKIBKC-UHFFFAOYSA-N 3-(2,2-dichloroethenoxy)benzaldehyde Chemical compound ClC(Cl)=COC1=CC=CC(C=O)=C1 WIMOGUTUZKIBKC-UHFFFAOYSA-N 0.000 claims description 6
241000238876 Acari Species 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
238000002474 experimental method Methods 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
241000256244 Heliothis virescens Species 0.000 claims description 5
241000256250 Spodoptera littoralis Species 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
238000010790 dilution Methods 0.000 claims description 5
239000012895 dilution Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
239000000047 product Substances 0.000 claims description 5
241001425390 Aphis fabae Species 0.000 claims description 4
241000196324 Embryophyta Species 0.000 claims description 4
241000238631 Hexapoda Species 0.000 claims description 4
244000061176 Nicotiana tabacum Species 0.000 claims description 4
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
241000949016 Rhipicephalus bursa Species 0.000 claims description 4
241000238680 Rhipicephalus microplus Species 0.000 claims description 4
244000061456 Solanum tuberosum Species 0.000 claims description 4
240000006677 Vicia faba Species 0.000 claims description 4
235000010749 Vicia faba Nutrition 0.000 claims description 4
239000013543 active substance Substances 0.000 claims description 4
239000004495 emulsifiable concentrate Substances 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000007921 spray Substances 0.000 claims description 4
239000000725 suspension Substances 0.000 claims description 4
239000004563 wettable powder Substances 0.000 claims description 4
241001124076 Aphididae Species 0.000 claims description 3
229920000742 Cotton Polymers 0.000 claims description 3
238000000746 purification Methods 0.000 claims description 3
VNTCVNLNEOVBEE-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=CC1C(C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-UHFFFAOYSA-N 0.000 claims 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 claims description 2
235000009161 Espostoa lanata Nutrition 0.000 claims description 2
240000001624 Espostoa lanata Species 0.000 claims description 2
241001674048 Phthiraptera Species 0.000 claims description 2
235000002098 Vicia faba var. major Nutrition 0.000 claims description 2
UKDFLTHAOGONOA-UHFFFAOYSA-N [cyano-[3-(2,2-dichloroethenoxy)phenyl]methyl] 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC(C#N)C1=CC=CC(OC=C(Cl)Cl)=C1 UKDFLTHAOGONOA-UHFFFAOYSA-N 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
238000011156 evaluation Methods 0.000 claims description 2
239000011521 glass Substances 0.000 claims description 2
230000001418 larval effect Effects 0.000 claims description 2
239000000575 pesticide Substances 0.000 claims description 2
239000002574 poison Substances 0.000 claims description 2
231100000614 poison Toxicity 0.000 claims description 2
230000008092 positive effect Effects 0.000 claims description 2
239000000741 silica gel Substances 0.000 claims description 2
229910002027 silica gel Inorganic materials 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
230000003129 miticidal effect Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
238000000034 method Methods 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
125000004435 hydrogen atom Chemical group [H]* 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
BKVGXKMHROLTHN-UHFFFAOYSA-N 1-(bromomethyl)-3-(2,2-dichloroethenoxy)benzene Chemical compound ClC(Cl)=COC1=CC=CC(CBr)=C1 BKVGXKMHROLTHN-UHFFFAOYSA-N 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
RZAQFIQNCOQIGP-UHFFFAOYSA-N 1-(2,2-dichloroethenoxy)-3-methylbenzene Chemical compound CC1=CC=CC(OC=C(Cl)Cl)=C1 RZAQFIQNCOQIGP-UHFFFAOYSA-N 0.000 description 3
JWMKUKRBNODZFA-UHFFFAOYSA-N 1-ethoxy-2-methylbenzene Chemical compound CCOC1=CC=CC=C1C JWMKUKRBNODZFA-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
241000255749 Coccinellidae Species 0.000 description 2
241000256113 Culicidae Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 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
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000607479 Yersinia pestis Species 0.000 description 2
230000000895 acaricidal effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
239000012230 colorless oil Substances 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
239000002270 dispersing agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 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
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
235000013311 vegetables Nutrition 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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
QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
VZYRNUGLRJASBP-UHFFFAOYSA-N 5-(2-octylsulfonylpropyl)-1,3-benzodioxole Chemical compound CCCCCCCCS(=O)(=O)C(C)CC1=CC=C2OCOC2=C1 VZYRNUGLRJASBP-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
241000907223 Bruchinae Species 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
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
241001466044 Delphacidae Species 0.000 description 1
241001481702 Dermanyssidae Species 0.000 description 1
241000131287 Dermestidae Species 0.000 description 1
241001414830 Diaspididae 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
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 0.000 description 1
101000687855 Homo sapiens Suppressor of cytokine signaling 3 Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000257159 Musca domestica Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
241000721621 Myzus persicae Species 0.000 description 1
241000488585 Panonychus Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
241000258921 Pulicidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001510071 Pyrrhocoridae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 1
102100024283 Suppressor of cytokine signaling 3 Human genes 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241001454294 Tetranychus Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000131339 Tipulidae Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 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
150000003857 carboxamides Chemical class 0.000 description 1
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
229960002327 chloral hydrate Drugs 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000004312 hexamethylene tetramine Substances 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
238000002156 mixing Methods 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
229910052757 nitrogen Inorganic materials 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
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
238000012545 processing Methods 0.000 description 1
FHQKDLNFTINTBW-UHFFFAOYSA-N prop-1-ynyl carbamate Chemical class CC#COC(N)=O FHQKDLNFTINTBW-UHFFFAOYSA-N 0.000 description 1
CQPJLZWBXXBTJA-UHFFFAOYSA-N prop-1-ynylphosphonic acid Chemical class CC#CP(O)(O)=O CQPJLZWBXXBTJA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
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 1
SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 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
125000005270 trialkylamine group Chemical group 0.000 description 1
ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
244000045561 useful plants Species 0.000 description 1
238000005406 washing Methods 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
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/53—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and hydroxy groups bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/562—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom
- C07C45/565—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with nitrogen as the only hetero atom by reaction with hexamethylene-tetramine

Landscapes

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

CH985975A 1975-07-28 1975-07-28 Dichlorovinyloxy-benzyl-cyclopropane-carboxylates CH600771A5 (en)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CH985975A CH600771A5 (en)	1975-07-28	1975-07-28	Dichlorovinyloxy-benzyl-cyclopropane-carboxylates
SU762381704A SU649295A3 (ru)	1975-07-28	1976-07-15	Инсектицидное средство
FR7622119A FR2319622A1 (fr)	1975-07-28	1976-07-20	Nouveaux esters cyclopropaniques utiles dans la lutte contre les parasites
US05/707,136 US4291056A (en)	1975-07-28	1976-07-20	Pesticidal esters
CA000257815A CA1171428A (fr)	1975-07-28	1976-07-26	Derives pesticides de cyclopropane-carboxylate de 3-(2,2-dichlorovinyloxy)benzyle
DE19762633551 DE2633551A1 (de)	1975-07-28	1976-07-26	Cyclopropankarbonsaeure-3-(2,2- dichlorvinyloxy)-benzylester, verfahren zu ihrer herstellung und ihre verwendung
IL50136A IL50136A0 (en)	1975-07-28	1976-07-27	Novel benzyl esters,their preparation and pesticidal compositions containing them
IT25752/76A IT1062142B (it)	1975-07-28	1976-07-27	Esteri 3 2.2 diclorovinilossi benzilici dell acido ciclopropan carbossilico procedimento per la loro preparazione e loro impiego come prodotti disinfestanti
GB31268/76A GB1561064A (en)	1975-07-28	1976-07-27	Esters
BE169258A BE844541A (fr)	1975-07-28	1976-07-27	Nouveaux esters cyclopropaniques
NL7608375A NL7608375A (nl)	1975-07-28	1976-07-28	Werkwijze voor het bereiden van nieuwe esters.
JP51090130A JPS6030301B2 (ja)	1975-07-28	1976-07-28	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

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH985975A CH600771A5 (en)	1975-07-28	1975-07-28	Dichlorovinyloxy-benzyl-cyclopropane-carboxylates

Publications (1)

Publication Number	Publication Date
CH600771A5 true CH600771A5 (en)	1978-06-30

Family

ID=4356451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH985975A CH600771A5 (en)	1975-07-28	1975-07-28	Dichlorovinyloxy-benzyl-cyclopropane-carboxylates

Country Status (3)

Country	Link
BE (1)	BE844541A (fr)
CH (1)	CH600771A5 (fr)
SU (1)	SU649295A3 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0010154A1 (fr) *	1978-09-21	1980-04-30	Bayer Ag	Compositions insecticides pour utilisation dans le sol, renfermant des esters benzyliques substitués (I) d'acides cyclopropane-carboxyliques comme agents actifs, procédé pour leur préparation, lutte contre les insectes terricoles à l'aide des esters (I) et d'esters benzyliques substitués d'acides cyclopropane-carboxyliques

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LV5118A3 (lv) *	1977-01-24	1993-06-10	Ici Plc	Insekticida sastavs

1975
- 1975-07-28 CH CH985975A patent/CH600771A5/de not_active IP Right Cessation
1976
- 1976-07-15 SU SU762381704A patent/SU649295A3/ru active
- 1976-07-27 BE BE169258A patent/BE844541A/fr not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0010154A1 (fr) *	1978-09-21	1980-04-30	Bayer Ag	Compositions insecticides pour utilisation dans le sol, renfermant des esters benzyliques substitués (I) d'acides cyclopropane-carboxyliques comme agents actifs, procédé pour leur préparation, lutte contre les insectes terricoles à l'aide des esters (I) et d'esters benzyliques substitués d'acides cyclopropane-carboxyliques

Also Published As

Publication number	Publication date
SU649295A3 (ru)	1979-02-25
BE844541A (fr)	1977-01-27

Legal Events

Date	Code	Title	Description
1991-03-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0001203A1 (fr)	1979-04-04	N-phényl-N'-benzoyl-urées, procédé pour leur préparation, produits les contenant, et leur utilisation comme pesticides
EP0000508B1 (fr)	1981-09-02	Phénylacétates de 2-oxypyridyle, leur procédé de préparation et leur utilisation comme pesticide
DE2731033A1 (de)	1978-01-26	2,2-dimethyl-3-isobutylcyclopropansaeureester
DE2706184A1 (de)	1977-08-18	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2805226A1 (de)	1978-08-17	Cyclopropankarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
DE2706222A1 (de)	1977-08-18	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2733740A1 (de)	1978-02-02	Cyclobutan-1-carboxylate, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
DE2647368A1 (de)	1977-05-05	Alpha-(1-pyrrolyl)-carbonsaeure-3- phenoxy-benzylester, verfahren zu ihrer herstellung und ihre verwendung
CH600771A5 (en)	1978-06-30	Dichlorovinyloxy-benzyl-cyclopropane-carboxylates
DE2633551A1 (de)	1977-02-17	Cyclopropankarbonsaeure-3-(2,2- dichlorvinyloxy)-benzylester, verfahren zu ihrer herstellung und ihre verwendung
DE2719561A1 (de)	1977-11-17	Chrysanthemumsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
DE2829329A1 (de)	1979-01-25	Cyclopropankarbonsaeureester und ihre salze mit anorganischen und organischen saeuren, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
EP0001795A1 (fr)	1979-05-16	Esters phénoxy-alpha-vinylbenzyliques d'acides cyclopropane carboxyliques, procédé pour leur préparation et leur utilisation comme pesticides
EP0007421A1 (fr)	1980-02-06	Esters d'acide alpha-isopropane-phénylacétique, leur préparation et leur utilisation comme pesticides
EP0029002B1 (fr)	1983-03-23	Phénylacétates, procédé pour leur préparation, et leur utilisation comme pesticides
CH623985A5 (en)	1981-07-15	A pesticide
DE2723236A1 (de)	1977-12-15	Spiroheptenylkarbonsaeureester, verfahren zu seiner herstellung und seine verwendung
CH602009A5 (en)	1978-07-14	Insecticidal cyclopropane carboxylates
CH602010A5 (en)	1978-07-14	Alkynyloxy-benzyl-cyclopropane-carboxylates
DE2548450A1 (de)	1976-05-13	Schaedlingsbekaempfungsmittel
DE2805274A1 (de)	1978-08-17	Cyclopropankarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung
DE2727909A1 (de)	1978-01-05	Spiroheptenylkarbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
CH611489A5 (en)	1979-06-15	Pesticides
CH602006A5 (en)	1978-07-14	Cyclopropane carboxylic esters
CH618319A5 (en)	1980-07-31	Pesticide

CH600771A5 - Dichlorovinyloxy-benzyl-cyclopropane-carboxylates - Google Patents

Info

Links

Classifications

Landscapes

Priority Applications (12)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4356451

Family Applications (1)

Country Status (3)

Cited By (1)

Families Citing this family (1)

Cited By (1)

Also Published As

Similar Documents

Legal Events