CA1076135A - 4-phenylbut-2-enyl esters of 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid and their use as pesticides - Google Patents
4-phenylbut-2-enyl esters of 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid and their use as pesticidesInfo
- Publication number
- CA1076135A CA1076135A CA238,661A CA238661A CA1076135A CA 1076135 A CA1076135 A CA 1076135A CA 238661 A CA238661 A CA 238661A CA 1076135 A CA1076135 A CA 1076135A
- Authority
- CA
- Canada
- Prior art keywords
- parts
- formula
- dimethyl
- compounds
- carboxylic acid
- Prior art date
- 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
Links
- -1 4-phenylbut-2-enyl esters Chemical class 0.000 title description 8
- 239000000575 pesticide Substances 0.000 title description 2
- CAOJXVMGSRHFGB-UHFFFAOYSA-N 3-ethenyl-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C)C1C(O)=O CAOJXVMGSRHFGB-UHFFFAOYSA-N 0.000 title 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000460 chlorine Substances 0.000 claims abstract description 7
- 239000011737 fluorine Chemical group 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 abstract description 2
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 229940022682 acetone Drugs 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
- 238000009835 boiling Methods 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000002904 solvent 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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000256244 Heliothis virescens Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 230000001276 controlling effect Effects 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000843 powder Substances 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
- 239000007921 spray Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 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
- 241000255925 Diptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 241000256250 Spodoptera littoralis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000000463 material 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
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium 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
- 238000001179 sorption measurement Methods 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 239000000758 substrate 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
- 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
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 1
- 241001427556 Anoplura 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
- BNARGNJKJAZKNK-UHFFFAOYSA-N CC#COP(O)=O Chemical class CC#COP(O)=O BNARGNJKJAZKNK-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241001466007 Heteroptera Species 0.000 description 1
- 241000257303 Hymenoptera Species 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
- 241001495069 Ischnocera Species 0.000 description 1
- 241000256602 Isoptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000258915 Leptinotarsa Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 241001415024 Psocoptera Species 0.000 description 1
- WABPPBHOPMUJHV-UHFFFAOYSA-N Sesamex Chemical compound CCOCCOCCOC(C)OC1=CC=C2OCOC2=C1 WABPPBHOPMUJHV-UHFFFAOYSA-N 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 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
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-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
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 235000015108 pies Nutrition 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000002360 preparation method 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 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
- 239000007858 starting material 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
- 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
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1466774A CH602009A5 (en) | 1974-11-01 | 1974-11-01 | Insecticidal cyclopropane carboxylates |
| CH589375 | 1975-05-07 | ||
| CH853975A CH611489A5 (en) | 1975-07-01 | 1975-07-01 | Pesticides |
| CH1301075 | 1975-10-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1076135A true CA1076135A (en) | 1980-04-22 |
Family
ID=27428952
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA238,661A Expired CA1076135A (en) | 1974-11-01 | 1975-10-30 | 4-phenylbut-2-enyl esters of 2,2-dimethyl-3-vinyl-cyclopropane carboxylic acid and their use as pesticides |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5173123A (enrdf_load_stackoverflow) |
| AT (1) | AT345033B (enrdf_load_stackoverflow) |
| BR (1) | BR7507163A (enrdf_load_stackoverflow) |
| CA (1) | CA1076135A (enrdf_load_stackoverflow) |
| DE (1) | DE2548450A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2289485A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1523736A (enrdf_load_stackoverflow) |
| IL (1) | IL48386A (enrdf_load_stackoverflow) |
| IT (1) | IT1045594B (enrdf_load_stackoverflow) |
| TR (1) | TR19005A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52151149A (en) * | 1976-06-09 | 1977-12-15 | Sumitomo Chem Co Ltd | Cyclopropanecarboxylic acid esters, their preparation, and insecticides and miticides containing same |
| FR2373966A1 (fr) * | 1976-12-16 | 1978-07-13 | Grouyellec Andre Le | Emploi du dimethylformamide comme synergisant et ameliorant les pyrethrines, pyrethrinoides et rotenones naturelles et de synthese |
| JP5076555B2 (ja) * | 2007-03-05 | 2012-11-21 | 東亞合成株式会社 | 害虫防除剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5638563B2 (enrdf_load_stackoverflow) * | 1973-07-28 | 1981-09-08 |
-
1975
- 1975-10-28 FR FR7532903A patent/FR2289485A1/fr active Granted
- 1975-10-29 DE DE19752548450 patent/DE2548450A1/de not_active Withdrawn
- 1975-10-30 IL IL48386A patent/IL48386A/xx unknown
- 1975-10-30 CA CA238,661A patent/CA1076135A/en not_active Expired
- 1975-10-31 BR BR7507163A patent/BR7507163A/pt unknown
- 1975-10-31 GB GB45411/75A patent/GB1523736A/en not_active Expired
- 1975-10-31 TR TR1900575A patent/TR19005A/xx unknown
- 1975-10-31 IT IT2893075A patent/IT1045594B/it active
- 1975-10-31 AT AT832075A patent/AT345033B/de not_active IP Right Cessation
- 1975-11-01 JP JP50132074A patent/JPS5173123A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5173123A (enrdf_load_stackoverflow) | 1976-06-24 |
| BR7507163A (pt) | 1976-08-10 |
| IT1045594B (it) | 1980-06-10 |
| DE2548450A1 (de) | 1976-05-13 |
| AT345033B (de) | 1978-08-25 |
| AU8613075A (en) | 1977-05-05 |
| FR2289485B1 (enrdf_load_stackoverflow) | 1979-07-13 |
| TR19005A (tr) | 1978-02-22 |
| IL48386A (en) | 1978-09-29 |
| GB1523736A (en) | 1978-09-06 |
| ATA832075A (de) | 1977-12-15 |
| IL48386A0 (en) | 1975-12-31 |
| FR2289485A1 (fr) | 1976-05-28 |
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