IL42406A - 3-methyl-1-oxo-2-(2-propynyl)-2-cyclopenten-4-yl ester of 2,2,3-tri-(or 2,2,3,3-tetra)methylcyclopropanecarboxylic acid,a process for preparing the same and insecticidal compositions containing the same - Google Patents
3-methyl-1-oxo-2-(2-propynyl)-2-cyclopenten-4-yl ester of 2,2,3-tri-(or 2,2,3,3-tetra)methylcyclopropanecarboxylic acid,a process for preparing the same and insecticidal compositions containing the sameInfo
- Publication number
- IL42406A IL42406A IL42406A IL4240673A IL42406A IL 42406 A IL42406 A IL 42406A IL 42406 A IL42406 A IL 42406A IL 4240673 A IL4240673 A IL 4240673A IL 42406 A IL42406 A IL 42406A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound
- acid
- same
- weight
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 37
- 230000000749 insecticidal effect Effects 0.000 title claims description 24
- -1 3-methyl-1-oxo-2-(2-propynyl)-2-cyclopenten-4-yl Chemical group 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- DIZKLZKLNKQFGB-UHFFFAOYSA-N 1-methylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1(C)CC1 DIZKLZKLNKQFGB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 44
- 241000255925 Diptera Species 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 18
- 239000007921 spray Substances 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000002316 fumigant Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000000443 aerosol Substances 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 150000008065 acid anhydrides Chemical class 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000002156 mixing Methods 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 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 12
- 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 12
- 229940024113 allethrin Drugs 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 241000256059 Culex pipiens Species 0.000 description 8
- 238000003197 gene knockdown Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000002917 insecticide Substances 0.000 description 7
- 239000003350 kerosene Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 241000257226 Muscidae Species 0.000 description 5
- 230000000266 injurious effect Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 4
- 239000010425 asbestos Substances 0.000 description 4
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 description 4
- 230000002147 killing effect Effects 0.000 description 4
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 229910052895 riebeckite Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000004563 wettable powder Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical class OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 239000004570 mortar (masonry) Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 description 2
- 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 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 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- 241000256054 Culex <genus> Species 0.000 description 2
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- FSYXMFXBRJFYBS-UHFFFAOYSA-N Furamethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(CC#C)O1 FSYXMFXBRJFYBS-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000004460 Tanacetum coccineum Species 0.000 description 2
- 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 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940008203 d-transallethrin Drugs 0.000 description 2
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 231100000636 lethal dose Toxicity 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 239000002728 pyrethroid Substances 0.000 description 2
- 229940015367 pyrethrum Drugs 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DBUJEFSBVCDNMS-UHFFFAOYSA-N (2,2,3-trimethylcyclopropanecarbonyl) 2,2,3-trimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C)C1C(=O)OC(=O)C1C(C)(C)C1C DBUJEFSBVCDNMS-UHFFFAOYSA-N 0.000 description 1
- LNJXZKBHJZAIKQ-UHFFFAOYSA-N 1,1,1,2-tetrachloro-3-(2,3,3,3-tetrachloropropoxy)propane Chemical compound ClC(Cl)(Cl)C(Cl)COCC(Cl)C(Cl)(Cl)Cl LNJXZKBHJZAIKQ-UHFFFAOYSA-N 0.000 description 1
- CCIGAUXGHSUZMV-UHFFFAOYSA-N 1,2,2-trimethylcyclopropane-1-carboxylic acid Chemical class CC1(C)CC1(C)C(O)=O CCIGAUXGHSUZMV-UHFFFAOYSA-N 0.000 description 1
- PAPVPNRFJQMQLS-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropane-1-carbonyl chloride Chemical compound CC1(C)C(C(Cl)=O)C1(C)C PAPVPNRFJQMQLS-UHFFFAOYSA-N 0.000 description 1
- NSRPQPHWALBONJ-UHFFFAOYSA-N 2,2,3-trimethylcyclopropane-1-carbonyl chloride Chemical compound CC1C(C(Cl)=O)C1(C)C NSRPQPHWALBONJ-UHFFFAOYSA-N 0.000 description 1
- DDZLZVXPBSNDAH-UHFFFAOYSA-N 2,2,3-trimethylcyclopropane-1-carboxylic acid Chemical compound CC1C(C(O)=O)C1(C)C DDZLZVXPBSNDAH-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IMPPGHMHELILKG-UHFFFAOYSA-N 4-ethoxyaniline Chemical compound CCOC1=CC=C(N)C=C1 IMPPGHMHELILKG-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- XSWGROKGWPUDPB-UHFFFAOYSA-N 4-methyl-3-propylbenzene-1,2-diol Chemical compound CCCC1=C(C)C=CC(O)=C1O XSWGROKGWPUDPB-UHFFFAOYSA-N 0.000 description 1
- 241000238657 Blattella germanica 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
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
- 201000006353 Filariasis Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257159 Musca domestica Species 0.000 description 1
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 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
- 235000014121 butter Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- WOPKYMRPOKFYNI-UHFFFAOYSA-N hydroxycyclopentenone Natural products OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 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
- 239000000178 monomer Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000003380 propellant Substances 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04B—TRANSMISSION
- H04B10/00—Transmission systems employing electromagnetic waves other than radio-waves, e.g. infrared, visible or ultraviolet light, or employing corpuscular radiation, e.g. quantum communication
- H04B10/50—Transmitters
Landscapes
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Engineering & Computer Science (AREA)
- Computer Networks & Wireless Communication (AREA)
- Signal Processing (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47054533A JPS50895B2 (en, 2012) | 1972-05-31 | 1972-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42406A0 IL42406A0 (en) | 1973-07-30 |
| IL42406A true IL42406A (en) | 1976-09-30 |
Family
ID=12973293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42406A IL42406A (en) | 1972-05-31 | 1973-05-30 | 3-methyl-1-oxo-2-(2-propynyl)-2-cyclopenten-4-yl ester of 2,2,3-tri-(or 2,2,3,3-tetra)methylcyclopropanecarboxylic acid,a process for preparing the same and insecticidal compositions containing the same |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3876681A (en, 2012) |
| JP (1) | JPS50895B2 (en, 2012) |
| AR (1) | AR202629A1 (en, 2012) |
| AU (1) | AU468421B2 (en, 2012) |
| BR (1) | BR7303985D0 (en, 2012) |
| CH (1) | CH578501A5 (en, 2012) |
| DE (1) | DE2327660C3 (en, 2012) |
| FR (1) | FR2186458B1 (en, 2012) |
| GB (1) | GB1394416A (en, 2012) |
| HK (1) | HK79176A (en, 2012) |
| IL (1) | IL42406A (en, 2012) |
| IT (1) | IT985262B (en, 2012) |
| MY (1) | MY7700056A (en, 2012) |
| PH (1) | PH10511A (en, 2012) |
| SU (1) | SU594883A3 (en, 2012) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE446527B (sv) * | 1976-09-21 | 1986-09-22 | Roussel Uclaf | Nya cyklopropankarboxylsyraestrar med en polyhalogenerad substituent, sett for framstellning derav samt anvendning derav i pesticidkompositioner |
| JPS5527104A (en) * | 1978-07-19 | 1980-02-27 | Sumitomo Chem Co Ltd | Pesticidal composition |
| FR2455025A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Esters de derives de l'allethrolone et d'acides cyclopropane carboxyliques, leurs procedes de preparation et les compositions les renfermant |
| AU541049B2 (en) * | 1980-10-09 | 1984-12-13 | Sumitomo Chemical Company, Limited | Cyclopropane carboxylates and their use as insectides |
| US6099850A (en) * | 1981-10-26 | 2000-08-08 | Battelle Memorial Institute | Termite and boring insect barrier for the protection of wooden structures |
| US6331308B1 (en) | 1981-10-26 | 2001-12-18 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US6060076A (en) * | 1981-10-26 | 2000-05-09 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US5925368A (en) * | 1981-10-26 | 1999-07-20 | Battelle Memorial Institute | Protection of wooden objects in direct contact with soil from pest invasion |
| JPS59168384U (ja) * | 1983-04-25 | 1984-11-10 | 大日本印刷株式会社 | 容器 |
| 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 |
| US6852328B1 (en) | 1989-09-01 | 2005-02-08 | Battelle Memorial Institute K1-53 | Method and device for protection of wooden objects proximate soil from pest invasion |
| US6572872B2 (en) | 1989-09-01 | 2003-06-03 | Battelle Memorial Institute | Method and apparatus for providing long term protection from intrusion by insects and other cold blooded animals |
| US6319511B1 (en) | 1989-09-01 | 2001-11-20 | Battelle Memorial Institute | Termite and boring insect barrier for the protection of wooden structures |
| US5856271A (en) * | 1995-06-07 | 1999-01-05 | Battelle Memorial Institute | Method of making controlled released devices |
| US20020192259A1 (en) * | 1998-02-25 | 2002-12-19 | Voris Peter Van | Barrier preventing wood pest access to wooden structures |
| US5985304A (en) | 1998-02-25 | 1999-11-16 | Battelle Memorial Institute | Barrier preventing wood pest access to wooden structures |
| US20060201053A1 (en) * | 2000-12-03 | 2006-09-14 | Voris Peter V | Barrier preventing wood pest access to wooden structures |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3636059A (en) * | 1966-07-20 | 1972-01-18 | Sumitomo Chemical Co | Cyclopentenolone esters |
| US3484489A (en) * | 1968-02-19 | 1969-12-16 | Hoffmann La Roche | Synthesis of hydroxyclopenten-1-ones |
| GB1305024A (en, 2012) * | 1969-07-10 | 1973-01-31 |
-
1972
- 1972-05-31 JP JP47054533A patent/JPS50895B2/ja not_active Expired
-
1973
- 1973-05-29 BR BR3985/73A patent/BR7303985D0/pt unknown
- 1973-05-29 AR AR248263A patent/AR202629A1/es active
- 1973-05-29 US US364271A patent/US3876681A/en not_active Expired - Lifetime
- 1973-05-30 IL IL42406A patent/IL42406A/en unknown
- 1973-05-30 DE DE2327660A patent/DE2327660C3/de not_active Expired
- 1973-05-30 FR FR7319760A patent/FR2186458B1/fr not_active Expired
- 1973-05-30 IT IT50356/73A patent/IT985262B/it active
- 1973-05-30 SU SU731921703A patent/SU594883A3/ru active
- 1973-05-30 GB GB2583973A patent/GB1394416A/en not_active Expired
- 1973-05-30 AU AU56278/73A patent/AU468421B2/en not_active Expired
- 1973-05-30 CH CH788173A patent/CH578501A5/xx not_active IP Right Cessation
- 1973-05-30 PH PH14676A patent/PH10511A/en unknown
-
1976
- 1976-12-16 HK HK791/76*UA patent/HK79176A/xx unknown
-
1977
- 1977-12-30 MY MY56/77A patent/MY7700056A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK79176A (en) | 1976-12-24 |
| CH578501A5 (en, 2012) | 1976-08-13 |
| PH10511A (en) | 1977-05-24 |
| SU594883A3 (ru) | 1978-02-25 |
| DE2327660A1 (de) | 1973-12-13 |
| JPS4919023A (en, 2012) | 1974-02-20 |
| DE2327660B2 (de) | 1977-10-27 |
| IT985262B (it) | 1974-11-30 |
| DE2327660C3 (de) | 1978-06-15 |
| MY7700056A (en) | 1977-12-31 |
| BR7303985D0 (pt) | 1974-07-18 |
| FR2186458B1 (en, 2012) | 1977-02-11 |
| AU468421B2 (en) | 1976-01-15 |
| AR202629A1 (es) | 1975-06-30 |
| JPS50895B2 (en, 2012) | 1975-01-13 |
| US3876681A (en) | 1975-04-08 |
| AU5627873A (en) | 1974-12-05 |
| FR2186458A1 (en, 2012) | 1974-01-11 |
| GB1394416A (en) | 1975-05-14 |
| IL42406A0 (en) | 1973-07-30 |
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