CH602006A5 - Cyclopropane carboxylic esters - Google Patents

Cyclopropane carboxylic esters

Info

Publication number: CH602006A5
Authority: CH; Switzerland
Prior art keywords: parts; sep; formula; compound; active component
Prior art date: 1975-04-07

Application number

CH436675A

Other languages

German (de)

English (en)

Inventor

Jozef Dr Drabek

Friedrich Dr Karrer

Laurenz Dr Gsell

Willy Meyer

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.)

1975-04-07

Filing date

1975-04-07

Publication date

1978-07-14

1975-04-07 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1975-04-07 Priority to CH436675A priority Critical patent/CH602006A5/de

1976-03-25 Priority to MX000116U priority patent/MX3200E/es

1976-04-02 Priority to NL7603488A priority patent/NL7603488A/xx

1976-04-05 Priority to DE19762614648 priority patent/DE2614648A1/de

1976-04-05 Priority to FR7609801A priority patent/FR2306971A1/fr

1976-04-05 Priority to CA249,592A priority patent/CA1092145A/fr

1976-04-06 Priority to AU12705/76A priority patent/AU497093B2/en

1976-04-06 Priority to EG76202A priority patent/EG12221A/xx

1976-04-06 Priority to SU762343604A priority patent/SU645523A3/ru

1976-04-06 Priority to ZA762061A priority patent/ZA762061B/xx

1976-04-06 Priority to BE165870A priority patent/BE840419A/fr

1976-04-06 Priority to TR18934A priority patent/TR18934A/xx

1976-04-06 Priority to GB13964/76A priority patent/GB1537873A/en

1976-04-06 Priority to HU76CI1651A priority patent/HU176210B/hu

1976-04-06 Priority to AT247376A priority patent/AT342921B/de

1976-04-06 Priority to IL7649357A priority patent/IL49357A0/xx

1976-04-06 Priority to BR7602093A priority patent/BR7602093A/pt

1976-04-07 Priority to JP51039152A priority patent/JPS51127051A/ja

1978-07-14 Publication of CH602006A5 publication Critical patent/CH602006A5/de

Links

YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title abstract 2
230000000895 acaricidal effect Effects 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 23
239000004480 active ingredient Substances 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
-1 3-phenoxy-benzyl Chemical group 0.000 claims description 9
239000000243 solution Substances 0.000 claims description 8
239000007921 spray Substances 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
241000256244 Heliothis virescens Species 0.000 claims description 5
241000238631 Hexapoda Species 0.000 claims description 5
241000256250 Spodoptera littoralis Species 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000839 emulsion Substances 0.000 claims description 5
230000000749 insecticidal effect Effects 0.000 claims description 5
241001425390 Aphis fabae Species 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
241000196324 Embryophyta Species 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
244000061176 Nicotiana tabacum Species 0.000 claims description 4
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
241001454293 Tetranychus urticae 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
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
235000013601 eggs Nutrition 0.000 claims description 4
239000004495 emulsifiable concentrate Substances 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
241001124076 Aphididae Species 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
239000012141 concentrate Substances 0.000 claims description 3
239000004615 ingredient Substances 0.000 claims description 3
239000000575 pesticide Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000004563 wettable powder Substances 0.000 claims description 3
UJUNUASMYSTBSK-UHFFFAOYSA-N 1-(bromomethyl)-3-phenoxybenzene Chemical compound BrCC1=CC=CC(OC=2C=CC=CC=2)=C1 UJUNUASMYSTBSK-UHFFFAOYSA-N 0.000 claims description 2
241000238876 Acari Species 0.000 claims description 2
244000046052 Phaseolus vulgaris Species 0.000 claims description 2
241001674048 Phthiraptera Species 0.000 claims description 2
244000119321 Phyllanthus reticulatus Species 0.000 claims description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 2
244000061456 Solanum tuberosum Species 0.000 claims description 2
235000002098 Vicia faba var. major Nutrition 0.000 claims description 2
238000009835 boiling Methods 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
239000012230 colorless oil Substances 0.000 claims description 2
239000012043 crude product Substances 0.000 claims description 2
238000010790 dilution Methods 0.000 claims description 2
239000012895 dilution Substances 0.000 claims description 2
235000005489 dwarf bean Nutrition 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
238000002474 experimental method Methods 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000005457 ice water Substances 0.000 claims description 2
238000004519 manufacturing process Methods 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
239000011541 reaction mixture Substances 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
235000011152 sodium sulphate Nutrition 0.000 claims description 2
239000000642 acaricide Substances 0.000 abstract description 2
239000002917 insecticide Substances 0.000 abstract description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000000034 method Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
239000005995 Aluminium silicate Substances 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
239000008187 granular material 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
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 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
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000255749 Coccinellidae Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
241001510071 Pyrrhocoridae Species 0.000 description 2
WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000007788 liquid Substances 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
239000007858 starting material Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 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
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
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000238660 Blattidae 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
229910014033 C-OH Inorganic materials 0.000 description 1
BNARGNJKJAZKNK-UHFFFAOYSA-N CC#COP(O)=O Chemical compound CC#COP(O)=O BNARGNJKJAZKNK-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
241001466044 Delphacidae Species 0.000 description 1
241001481702 Dermanyssidae 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
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 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
241001415279 Pseudococcidae Species 0.000 description 1
241000258921 Pulicidae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000607479 Yersinia pestis Species 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
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
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 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
239000000428 dust Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
238000009472 formulation Methods 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
150000004679 hydroxides Chemical class 0.000 description 1
229920013821 hydroxy alkyl cellulose Polymers 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 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
239000006072 paste Substances 0.000 description 1
150000003018 phosphorus compounds Chemical class 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 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

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

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH436675A 1975-04-07 1975-04-07 Cyclopropane carboxylic esters CH602006A5 (en)

Priority Applications (18)

Application Number	Priority Date	Filing Date	Title
CH436675A CH602006A5 (en)	1975-04-07	1975-04-07	Cyclopropane carboxylic esters
MX000116U MX3200E (es)	1975-04-07	1976-03-25	Procedimiento para la preparacion de esteres de acido ciclo propan carboxilico
NL7603488A NL7603488A (nl)	1975-04-07	1976-04-02	Werkwijze voor het bereiden van nieuwe esters.
DE19762614648 DE2614648A1 (de)	1975-04-07	1976-04-05	Cyclopropankarbonsaeureester
FR7609801A FR2306971A1 (fr)	1975-04-07	1976-04-05	Nouveaux esters d'acide cyclopropane-carboxylique, leur application a la lutte contre les parasites et leur procede de preparation
CA249,592A CA1092145A (fr)	1975-04-07	1976-04-05	Derives du carboxylate de metaphenoxybenzylcyclopropane employe comme pesticide
AU12705/76A AU497093B2 (en)	1975-04-07	1976-04-06	Cyclopropane carboxylic acid esters of use as pest control agents
EG76202A EG12221A (en)	1975-04-07	1976-04-06	Cyclopropanecarboxylic acid esters and their use in pest control
SU762343604A SU645523A3 (ru)	1975-04-07	1976-04-06	Инсектицидно-акарицидное средство
ZA762061A ZA762061B (en)	1975-04-07	1976-04-06	New esters
BE165870A BE840419A (fr)	1975-04-07	1976-04-06	Nouveaux esters d'acide cyclopropane-carboxylique, leur application a la lutte contre les parasites et leur procede de preparation
TR18934A TR18934A (tr)	1975-04-07	1976-04-06	Yeni esterler
GB13964/76A GB1537873A (en)	1975-04-07	1976-04-06	Cyclopropane carboxylic acid esters
HU76CI1651A HU176210B (en)	1975-04-07	1976-04-06	Pesticide compositions containing cyclopropanecarboxylic acid esters and process for producing the esters of cyclopropanecarboxylic acids
AT247376A AT342921B (de)	1975-04-07	1976-04-06	Insektizides und akarizides mittel
IL7649357A IL49357A0 (en)	1975-04-07	1976-04-06	New cyclopropanecarboxylic acid esters,their production and their use as pesticides
BR7602093A BR7602093A (pt)	1975-04-07	1976-04-06	Processo para a preparacao de um ester de acido ciclopropanocarboxilico,composicao para combater parasitas e sua aplicacao
JP51039152A JPS51127051A (en)	1975-04-07	1976-04-07	Cyclopropane carboxylic acid ester and process for manufacture thereof and insecticides containing said compound

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH436675A CH602006A5 (en)	1975-04-07	1975-04-07	Cyclopropane carboxylic esters

Publications (1)

Publication Number	Publication Date
CH602006A5 true CH602006A5 (en)	1978-07-14

Family

ID=4274757

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH436675A CH602006A5 (en)	1975-04-07	1975-04-07	Cyclopropane carboxylic esters

Country Status (4)

Country	Link
BE (1)	BE840419A (fr)
CH (1)	CH602006A5 (fr)
SU (1)	SU645523A3 (fr)
ZA (1)	ZA762061B (fr)

1975
- 1975-04-07 CH CH436675A patent/CH602006A5/de not_active IP Right Cessation
1976
- 1976-04-06 ZA ZA762061A patent/ZA762061B/xx unknown
- 1976-04-06 SU SU762343604A patent/SU645523A3/ru active
- 1976-04-06 BE BE165870A patent/BE840419A/fr unknown

Also Published As

Publication number	Publication date
ZA762061B (en)	1977-04-27
SU645523A3 (ru)	1979-01-30
BE840419A (fr)	1976-10-06

Legal Events

Date	Code	Title	Description
1981-12-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
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DE2418295C2 (de)	1986-04-03	Substituierte Benzyloxydiphenyläther, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
EP0004030A2 (fr)	1979-09-19	N-phényl-N'-fluorobenzoyl urées substituées, leurs procédés de préparation et leur utilisation comme pesticides
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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
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DE2642850A1 (de)	1977-04-07	2,2-dimethyl-4,5-benzospiro(2,4)heptan- und 2,2-dimethyl-4,5-benzospiro (2,4)hepta-4,6-dien-1-carbonsaeureester, verfahren zu ihrer herstellung und schaedlingsbekaempfungsmittel
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DE2713651A1 (de)	1977-10-13	Spiro-(2,4)-hepta-1-carboxylate, verfahren zu ihrer herstellung und ihre verwendung
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CH611489A5 (en)	1979-06-15	Pesticides
CH618319A5 (en)	1980-07-31	Pesticide