CS203967B2 - Insecticide means - Google Patents
Insecticide means Download PDFInfo
- Publication number
- CS203967B2 CS203967B2 CS736689A CS668973A CS203967B2 CS 203967 B2 CS203967 B2 CS 203967B2 CS 736689 A CS736689 A CS 736689A CS 668973 A CS668973 A CS 668973A CS 203967 B2 CS203967 B2 CS 203967B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- cis
- trans
- chrysantemate
- methyl
- chrysantemic
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title description 10
- 239000000203 mixture Substances 0.000 claims abstract description 71
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 41
- 239000004480 active ingredient Substances 0.000 claims abstract description 14
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims abstract description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 47
- 150000002148 esters Chemical class 0.000 claims description 47
- -1 methyl-3-phenoxybenzyl Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 39
- XLOPRKKSAJMMEW-SFYZADRCSA-N (+)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 abstract description 10
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical group CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract description 8
- XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- IAKOZHOLGAGEJT-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(p-methoxyphenyl)-Ethane Chemical compound C1=CC(OC)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(OC)C=C1 IAKOZHOLGAGEJT-UHFFFAOYSA-N 0.000 abstract description 2
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 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 abstract description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 abstract description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003337 fertilizer Substances 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 239000000201 insect hormone Substances 0.000 abstract description 2
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 abstract description 2
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound 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 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000006096 absorbing agent Substances 0.000 abstract 1
- 230000003078 antioxidant effect Effects 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- 241000255925 Diptera Species 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 230000002195 synergetic effect Effects 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000000443 aerosol Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 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 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- XLOPRKKSAJMMEW-YUMQZZPRSA-N (+)-cis-chrysanthemic acid Chemical compound CC(C)=C[C@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-YUMQZZPRSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 206010033799 Paralysis Diseases 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 241000257226 Muscidae Species 0.000 description 5
- 238000003776 cleavage reaction Methods 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000001769 paralizing effect Effects 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000256059 Culex pipiens Species 0.000 description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000391 smoking effect Effects 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VSBPRBXTUAKKSY-UHFFFAOYSA-N 5-(5-methyl-1,3-dioxan-4-yl)-1,3-benzodioxole Chemical compound CC1COCOC1C1=CC=C(OCO2)C2=C1 VSBPRBXTUAKKSY-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000010425 asbestos Substances 0.000 description 3
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 229910052895 riebeckite Inorganic materials 0.000 description 3
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229960005235 piperonyl butoxide Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- KGANAERDZBAECK-UHFFFAOYSA-N (3-phenoxyphenyl)methanol Chemical compound OCC1=CC=CC(OC=2C=CC=CC=2)=C1 KGANAERDZBAECK-UHFFFAOYSA-N 0.000 description 1
- AFEOKIGLYCQHAZ-UHFFFAOYSA-N (5-benzylfuran-3-yl)methanol Chemical compound OCC1=COC(CC=2C=CC=CC=2)=C1 AFEOKIGLYCQHAZ-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- ISFGTDAAYLSOFY-UHFFFAOYSA-N 4-hydroxy-3-methyl-2-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1=C(CC#C)C(=O)CC1O ISFGTDAAYLSOFY-UHFFFAOYSA-N 0.000 description 1
- CSXOGACWYJFTLV-UHFFFAOYSA-N 4-methyl-5-propyl-1,3-benzodioxole Chemical compound CCCC1=CC=C2OCOC2=C1C CSXOGACWYJFTLV-UHFFFAOYSA-N 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 244000147058 Derris elliptica Species 0.000 description 1
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 240000004460 Tanacetum coccineum Species 0.000 description 1
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
- IXEVGHXRXDBAOB-BREBYQMCSA-N [(1r,3r,4r)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-thiocyanatoacetate Chemical compound C1C[C@@]2(C)[C@H](OC(=O)CSC#N)C[C@@H]1C2(C)C IXEVGHXRXDBAOB-BREBYQMCSA-N 0.000 description 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- WLLGXSLBOPFWQV-OTHKPKEBSA-N molport-035-783-878 Chemical compound C([C@H]1C=C2)[C@H]2C2C1C(=O)N(CC(CC)CCCC)C2=O WLLGXSLBOPFWQV-OTHKPKEBSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 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
- 239000005645 nematicide Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012794 pre-harvesting Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
- JUVIOZPCNVVQFO-UHFFFAOYSA-N rotenone Natural products O1C2=C3CC(C(C)=C)OC3=CC=C2C(=O)C2C1COC1=C2C=C(OC)C(OC)=C1 JUVIOZPCNVVQFO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- C07D209/49—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS76341A CS203968B2 (cs) | 1972-09-29 | 1976-01-20 | Insekticidní prostředek na bázi esterů kyseliny chryzantémové |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9845872A JPS5516402B2 (en, 2012) | 1972-09-29 | 1972-09-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS203967B2 true CS203967B2 (en) | 1981-03-31 |
Family
ID=14220246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS736689A CS203967B2 (en) | 1972-09-29 | 1973-09-28 | Insecticide means |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US3934023A (en, 2012) |
| JP (1) | JPS5516402B2 (en, 2012) |
| AT (1) | AT332679B (en, 2012) |
| BE (1) | BE805442A (en, 2012) |
| BR (1) | BR7307536D0 (en, 2012) |
| CA (1) | CA1007564A (en, 2012) |
| CH (2) | CH595063A5 (en, 2012) |
| CS (1) | CS203967B2 (en, 2012) |
| DD (1) | DD106775A5 (en, 2012) |
| DE (1) | DE2348930C3 (en, 2012) |
| DK (1) | DK139702B (en, 2012) |
| EG (1) | EG11400A (en, 2012) |
| FI (1) | FI56475C (en, 2012) |
| FR (1) | FR2201036B1 (en, 2012) |
| GB (1) | GB1443533A (en, 2012) |
| HK (1) | HK9277A (en, 2012) |
| HU (1) | HU177749B (en, 2012) |
| IN (1) | IN138685B (en, 2012) |
| IT (1) | IT1053522B (en, 2012) |
| KE (1) | KE2701A (en, 2012) |
| MX (1) | MX3300E (en, 2012) |
| MY (1) | MY7700179A (en, 2012) |
| NL (1) | NL150308B (en, 2012) |
| NO (1) | NO138318C (en, 2012) |
| OA (1) | OA04557A (en, 2012) |
| PH (1) | PH10808A (en, 2012) |
| PL (2) | PL98702B1 (en, 2012) |
| RO (1) | RO71392A (en, 2012) |
| SE (2) | SE417267B (en, 2012) |
| SU (2) | SU664529A3 (en, 2012) |
| TR (1) | TR19267A (en, 2012) |
| YU (1) | YU257173A (en, 2012) |
| ZA (1) | ZA737516B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537499B2 (en, 2012) * | 1974-12-05 | 1978-03-18 | ||
| AU1973076A (en) * | 1975-11-19 | 1978-05-25 | Wellcome Australasia Limited | Pyrethroid and organophosphorus composition |
| ZA785688B (en) * | 1977-10-11 | 1980-05-28 | Wellcome Found | Pesticidal compositions |
| AU528416B2 (en) * | 1978-05-30 | 1983-04-28 | Wellcome Foundation Limited, The | Pesticidal formulations |
| JPS5527104A (en) * | 1978-07-19 | 1980-02-27 | Sumitomo Chem Co Ltd | Pesticidal composition |
| FR2451161A1 (fr) * | 1979-03-16 | 1980-10-10 | Roussel Uclaf | Melanges synergiques a base d'esters de (s) allethrolone et de (r) allethrolone, doues d'activite contre les arthropodes |
| JPS562929A (en) * | 1979-06-21 | 1981-01-13 | Sumitomo Chem Co Ltd | Preparation of optically active cyclopentenolone |
| JPS5620546A (en) * | 1979-07-27 | 1981-02-26 | Sumitomo Chem Co Ltd | Carboxylic acid ester |
| DE3061543D1 (en) * | 1979-09-06 | 1983-02-10 | Sumitomo Chemical Co | Cis-(1r,2s)-3,3-dimethyl-2-((4s)-3-methyl-2-(2-propynyl)cyclopent-2-en-1-on-4-yloxyhydroxymethyl)-cyclopropanecarboxylic lactone and method of producing (s)-4-hydroxy-3-methyl-2-(2-propynyl)-cyclopent-2-en-1-on |
| EG18025A (en) * | 1986-07-18 | 1993-06-30 | Sumitomo Chemical Co | A method for killing insects by heating fumigation |
| EG18369A (en) * | 1986-08-15 | 1992-10-30 | Sumitomo Chemical Co | An insecticidal composition for electric fumigator |
| JP2570388B2 (ja) * | 1988-06-10 | 1997-01-08 | 住友化学工業株式会社 | カルボン酸エステルおよびその殺虫剤としての用途 |
| JP3052142B2 (ja) * | 1989-09-14 | 2000-06-12 | 住友化学工業株式会社 | 殺虫、殺ダニ組成物 |
| AU653453B2 (en) * | 1991-12-27 | 1994-09-29 | Sumitomo Chemical Company, Limited | Insecticidal compositions |
| US5468497A (en) * | 1993-09-03 | 1995-11-21 | Dainihon Jochugiku Co., Ltd. | Fuming, hot-vaporizing insecticide for killing flies, and method for killing flies with the same |
| RU2176448C2 (ru) * | 1999-11-19 | 2001-12-10 | Открытое акционерное общество "Арнест" | Инсектицидный препарат |
| AU2011265562A1 (en) * | 2011-01-12 | 2012-07-26 | Sumitomo Chemical Company, Limited | Method of controlling harmful arthropod, composition, and electrostatic spray device |
| JP2012153608A (ja) * | 2011-01-21 | 2012-08-16 | Sumitomo Chemical Co Ltd | 有害節足動物の防除方法、組成物、静電噴霧装置 |
| JO3626B1 (ar) | 2012-02-23 | 2020-08-27 | Merial Inc | تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها |
| WO2018050213A1 (en) | 2016-09-14 | 2018-03-22 | Endura S.P.A. | Improved process for the preparation of pyrethroids |
| AU2019309520B2 (en) | 2018-07-27 | 2025-04-03 | Aperta Biosciences, Llc | Spinosyn formulations for treatment of demodex-induced ocular and facial conditions |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE635902A (en, 2012) * | 1962-08-06 | |||
| US3702333A (en) * | 1967-08-11 | 1972-11-07 | Yoshitomi Pharmaceutical | Cyclopropanecarboxylic acid esters possessing pesticidal properties |
| ZA708448B (en) * | 1969-12-24 | 1971-09-29 | Sumitomo Chemical Co | Novel insecticidal compositions |
| FR2077677B1 (en, 2012) * | 1970-02-04 | 1973-05-25 | Roussel Uclaf | |
| AU432259B1 (en) * | 1970-02-26 | 1972-08-24 | Sumitomo Chemical Company, Limited | Novel substituted chrysanthemates |
| US3714153A (en) * | 1970-06-22 | 1973-01-30 | Roussel Uclaf | Novel cyclopropanecarboxylic acids |
-
1972
- 1972-09-29 JP JP9845872A patent/JPS5516402B2/ja not_active Expired
-
1973
- 1973-09-19 NO NO3674/73A patent/NO138318C/no unknown
- 1973-09-24 ZA ZA737516*A patent/ZA737516B/xx unknown
- 1973-09-24 IN IN2165/CAL/73A patent/IN138685B/en unknown
- 1973-09-26 GB GB4514173A patent/GB1443533A/en not_active Expired
- 1973-09-26 OA OA55018A patent/OA04557A/xx unknown
- 1973-09-26 US US05/401,034 patent/US3934023A/en not_active Expired - Lifetime
- 1973-09-27 FI FI3018/73A patent/FI56475C/fi active
- 1973-09-27 SE SE7313185A patent/SE417267B/xx unknown
- 1973-09-27 CH CH231077A patent/CH595063A5/xx not_active IP Right Cessation
- 1973-09-27 BR BR7536/73A patent/BR7307536D0/pt unknown
- 1973-09-27 SU SU731961454A patent/SU664529A3/ru active
- 1973-09-27 DK DK530273AA patent/DK139702B/da not_active IP Right Cessation
- 1973-09-27 TR TR19267A patent/TR19267A/xx unknown
- 1973-09-27 FR FR7334658A patent/FR2201036B1/fr not_active Expired
- 1973-09-27 CH CH1386473A patent/CH595062A5/xx not_active IP Right Cessation
- 1973-09-28 PH PH15066A patent/PH10808A/en unknown
- 1973-09-28 YU YU02571/73A patent/YU257173A/xx unknown
- 1973-09-28 AT AT836073A patent/AT332679B/de not_active IP Right Cessation
- 1973-09-28 DE DE2348930A patent/DE2348930C3/de not_active Expired
- 1973-09-28 BE BE136149A patent/BE805442A/xx not_active IP Right Cessation
- 1973-09-28 NL NL737313373A patent/NL150308B/xx not_active IP Right Cessation
- 1973-09-28 CA CA182,160A patent/CA1007564A/en not_active Expired
- 1973-09-28 MX MX005222U patent/MX3300E/es unknown
- 1973-09-28 CS CS736689A patent/CS203967B2/cs unknown
- 1973-09-28 DD DD173765A patent/DD106775A5/xx unknown
- 1973-09-28 HU HU73SU840A patent/HU177749B/hu unknown
- 1973-09-28 IT IT52830/73A patent/IT1053522B/it active
- 1973-09-29 PL PL1973165532A patent/PL98702B1/xx unknown
- 1973-09-29 RO RO7376202A patent/RO71392A/ro unknown
- 1973-09-29 EG EG378/73A patent/EG11400A/xx active
- 1973-09-29 PL PL1973189104A patent/PL99484B1/pl unknown
-
1975
- 1975-08-20 SU SU7502167199A patent/SU572171A3/ru active
-
1976
- 1976-09-30 SE SE7610860A patent/SE430298B/sv not_active IP Right Cessation
-
1977
- 1977-02-03 KE KE2701A patent/KE2701A/xx unknown
- 1977-02-17 HK HK92/77A patent/HK9277A/xx unknown
- 1977-12-30 MY MY179/77A patent/MY7700179A/xx unknown
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