JPH0458463B2 - - Google Patents
Info
- Publication number
- JPH0458463B2 JPH0458463B2 JP24694584A JP24694584A JPH0458463B2 JP H0458463 B2 JPH0458463 B2 JP H0458463B2 JP 24694584 A JP24694584 A JP 24694584A JP 24694584 A JP24694584 A JP 24694584A JP H0458463 B2 JPH0458463 B2 JP H0458463B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ring
- formula
- methyl group
- hydrogen atom
- 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
- 150000001875 compounds Chemical class 0.000 claims description 61
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002837 carbocyclic group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 241000255925 Diptera Species 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000007921 spray Substances 0.000 claims description 2
- 229910052799 carbon Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- -1 5-bromo-2-naphthyl group Chemical group 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 241000257226 Muscidae Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001608567 Phaedon cochleariae Species 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- DMYZVIYUOGRVKV-UHFFFAOYSA-N 1-bromo-6-(2-methoxyethenyl)naphthalene Chemical compound BrC1=CC=CC2=CC(C=COC)=CC=C21 DMYZVIYUOGRVKV-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229940100595 phenylacetaldehyde Drugs 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- CWRAIVVKAOLKKW-UHFFFAOYSA-N (5,8-dibromonaphthalen-2-yl)methanol Chemical compound BrC1=CC=C(Br)C2=CC(CO)=CC=C21 CWRAIVVKAOLKKW-UHFFFAOYSA-N 0.000 description 1
- WQWYMTQBTFOERJ-UHFFFAOYSA-N (5-bromonaphthalen-2-yl)methanol Chemical compound BrC1=CC=CC2=CC(CO)=CC=C21 WQWYMTQBTFOERJ-UHFFFAOYSA-N 0.000 description 1
- MAARRMBCEFVKNV-UHFFFAOYSA-N (6-bromonaphthalen-2-yl)methanol Chemical compound C1=C(Br)C=CC2=CC(CO)=CC=C21 MAARRMBCEFVKNV-UHFFFAOYSA-N 0.000 description 1
- XELUGVOOQAQZLM-UHFFFAOYSA-N (9-bromophenanthren-3-yl)methanol Chemical compound C1=CC=C2C3=CC(CO)=CC=C3C=C(Br)C2=C1 XELUGVOOQAQZLM-UHFFFAOYSA-N 0.000 description 1
- KJMZGQZAIQDEKS-ONEGZZNKSA-N (e)-4-bromo-n-(2-methylpropyl)but-2-enamide Chemical compound CC(C)CNC(=O)\C=C\CBr KJMZGQZAIQDEKS-ONEGZZNKSA-N 0.000 description 1
- ACFFAMJSFZINGL-OWOJBTEDSA-N (e)-4-bromobut-2-enoyl chloride Chemical compound ClC(=O)\C=C\CBr ACFFAMJSFZINGL-OWOJBTEDSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NQLUBPPKLOJHRM-UHFFFAOYSA-N 1-(2-methoxyethenyl)naphthalene Chemical compound C1=CC=C2C(C=COC)=CC=CC2=C1 NQLUBPPKLOJHRM-UHFFFAOYSA-N 0.000 description 1
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- HHSDZLLPIXMEIU-UHFFFAOYSA-N 1-bromoheptadecane Chemical compound CCCCCCCCCCCCCCCCCBr HHSDZLLPIXMEIU-UHFFFAOYSA-N 0.000 description 1
- DHATYXHTVNBHOK-UHFFFAOYSA-N 2-(5-bromonaphthalen-2-yl)acetaldehyde Chemical compound O=CCC1=CC=C2C(Br)=CC=CC2=C1 DHATYXHTVNBHOK-UHFFFAOYSA-N 0.000 description 1
- ODBRNYAPXJRRPQ-UHFFFAOYSA-N 2-(9,10-dihydrophenanthren-2-yl)acetaldehyde Chemical compound C1=CC=C2C3=CC=C(CC=O)C=C3CCC2=C1 ODBRNYAPXJRRPQ-UHFFFAOYSA-N 0.000 description 1
- TXUORHUVNHUMSO-UHFFFAOYSA-N 2-(9h-fluoren-1-yl)acetaldehyde Chemical compound C1C2=CC=CC=C2C2=C1C(CC=O)=CC=C2 TXUORHUVNHUMSO-UHFFFAOYSA-N 0.000 description 1
- FXSCJZNMWILAJO-UHFFFAOYSA-N 2-bromo-9h-fluorene Chemical compound C1=CC=C2C3=CC=C(Br)C=C3CC2=C1 FXSCJZNMWILAJO-UHFFFAOYSA-N 0.000 description 1
- XHYSOHAVAXNPLA-UHFFFAOYSA-N 2-dibenzofuran-2-ylacetaldehyde Chemical compound C1=CC=C2C3=CC(CC=O)=CC=C3OC2=C1 XHYSOHAVAXNPLA-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- ZONWDLKOOMKAKI-UHFFFAOYSA-N 2-naphthalen-2-ylacetaldehyde Chemical compound C1=CC=CC2=CC(CC=O)=CC=C21 ZONWDLKOOMKAKI-UHFFFAOYSA-N 0.000 description 1
- DKKVCTJKCQECOZ-UHFFFAOYSA-N 2-phenanthren-2-ylacetaldehyde Chemical compound C1=CC=C2C3=CC=C(CC=O)C=C3C=CC2=C1 DKKVCTJKCQECOZ-UHFFFAOYSA-N 0.000 description 1
- FPHLLRFNNJTCAC-UHFFFAOYSA-N 5,8-dibromonaphthalene-2-carbaldehyde Chemical compound O=CC1=CC=C2C(Br)=CC=C(Br)C2=C1 FPHLLRFNNJTCAC-UHFFFAOYSA-N 0.000 description 1
- OQAFFLFJQFWYHB-UHFFFAOYSA-N 5-bromonaphthalene-2-carbaldehyde Chemical compound O=CC1=CC=C2C(Br)=CC=CC2=C1 OQAFFLFJQFWYHB-UHFFFAOYSA-N 0.000 description 1
- DLLDUYJRQNTEOR-UHFFFAOYSA-N 6-bromonaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(Br)=CC=C21 DLLDUYJRQNTEOR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WFGBHJZNFVZEEP-UHFFFAOYSA-N 8-naphthalen-2-yloxyoctan-1-ol Chemical compound C1=CC=CC2=CC(OCCCCCCCCO)=CC=C21 WFGBHJZNFVZEEP-UHFFFAOYSA-N 0.000 description 1
- RRZHHGATRMQHIP-UHFFFAOYSA-N 8-naphthalen-2-yloxyoctanal Chemical compound C1=CC=CC2=CC(OCCCCCCCC=O)=CC=C21 RRZHHGATRMQHIP-UHFFFAOYSA-N 0.000 description 1
- UWFVZTDQILEQMH-UHFFFAOYSA-N 9,10-dihydrophenanthren-2-ylmethanol Chemical compound C1=CC=C2C3=CC=C(CO)C=C3CCC2=C1 UWFVZTDQILEQMH-UHFFFAOYSA-N 0.000 description 1
- OPUUJVDNMHYQGM-UHFFFAOYSA-N 9,10-dihydrophenanthrene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(C=O)C=C3CCC2=C1 OPUUJVDNMHYQGM-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- SKJDSXMBUATPMY-WLHGVMLRSA-N BrC/C=C/C(=O)O.C(C(C)C)NC(C=CCBr)=O Chemical compound BrC/C=C/C(=O)O.C(C(C)C)NC(C=CCBr)=O SKJDSXMBUATPMY-WLHGVMLRSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VFVZOCRDMWIPLR-UHFFFAOYSA-N CC(C1=C(C=C2)OC3=C1C=CC=C3)=C2OC=C Chemical compound CC(C1=C(C=C2)OC3=C1C=CC=C3)=C2OC=C VFVZOCRDMWIPLR-UHFFFAOYSA-N 0.000 description 1
- TWXAUOALZCEBLY-UHFFFAOYSA-N CC1=C(C=CC2=C1C=CC3=CC=CC=C32)OC=C Chemical compound CC1=C(C=CC2=C1C=CC3=CC=CC=C32)OC=C TWXAUOALZCEBLY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical group C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002535 acidifier Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 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
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000003197 gene knockdown Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- HVPRQCPIJRYXQV-UHFFFAOYSA-N phenanthren-2-ylmethanol Chemical compound C1=CC=C2C3=CC=C(CO)C=C3C=CC2=C1 HVPRQCPIJRYXQV-UHFFFAOYSA-N 0.000 description 1
- GKROKAVBUIADBS-UHFFFAOYSA-N phenanthrene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(C=O)C=C3C=CC2=C1 GKROKAVBUIADBS-UHFFFAOYSA-N 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838331036A GB8331036D0 (en) | 1983-11-21 | 1983-11-21 | Pesticides |
| GB8331036 | 1983-12-07 | ||
| GB8332630 | 1983-12-07 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4065822A Division JPH0699375B2 (ja) | 1983-11-21 | 1992-03-24 | クロトンアミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60132944A JPS60132944A (ja) | 1985-07-16 |
| JPH0458463B2 true JPH0458463B2 (de) | 1992-09-17 |
Family
ID=10552108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24694584A Granted JPS60132944A (ja) | 1983-11-21 | 1984-11-20 | 殺虫剤 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS60132944A (de) |
| GB (1) | GB8331036D0 (de) |
-
1983
- 1983-11-21 GB GB838331036A patent/GB8331036D0/en active Pending
-
1984
- 1984-11-20 JP JP24694584A patent/JPS60132944A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB8331036D0 (en) | 1983-12-29 |
| JPS60132944A (ja) | 1985-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4263319A (en) | 4-Substituted-2-indanol insecticidal ester derivatives | |
| JPH0120143B2 (de) | ||
| US4551546A (en) | Halogenated esters | |
| CA1130308A (en) | Preparation of cyclopropane carboxylic acids and esters | |
| US4157447A (en) | Intermediates for insecticidal (β-phenyl-β-substituted-vinyl)cyclopropanecarboxylates | |
| JPH05331120A (ja) | クロトンアミド誘導体 | |
| US4200644A (en) | Arylthiovinylcyclopropanecarboxylate insecticides | |
| EP0069761B1 (de) | (+)-4-substituierte 2-indanole und insektizide esterderivate | |
| US3683005A (en) | Cyclopropanecarboxylic acid esters | |
| US4157397A (en) | Insecticidal (β-phenylvinyl)cyclopropanecarboxylates | |
| Rossi et al. | Stereospecific synthesis of (Z)-13-hexadecen-11-yn-1-yl acetate: The sex pheromone of the processionary moth, and of (5Z, 7E)-5, 7-dodecadien-1-ol, a sex pheromone component of the forest tent caterpillar | |
| JPH0458463B2 (de) | ||
| US4335252A (en) | Insecticidal pyrethroid enantiomer pair | |
| US4368205A (en) | 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives | |
| US4315029A (en) | Racemic modification consisting of specific isomers of α-cyano-3-phenoxybenzyl cis- or trans-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate, production thereof and pesticidal compositions containing the same | |
| US4346251A (en) | 4-Substituted-2-indanols | |
| US4429149A (en) | 4-Phenyl-2-indanyl esters of 1R,cis-3-(2-halo-3,3,3-trifluoropropenyl)-2,2-dimethylcyclopropanecarboxylic acid | |
| GB2044769A (en) | Pyrethroids their preparation and use as insecticides | |
| US4408057A (en) | 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives | |
| US4778822A (en) | Insecticidally active ester | |
| US4485238A (en) | Preparation of ((6-substituted phenoxy-2-pyridinyl)-methyl)-3-(2,2-bis(trifluoromethyl)-1-ethenyl)-2,2-dimethylcyclopropane carboxylates | |
| JPS597195A (ja) | チオールリン酸エステル、その製造法および殺虫剤 | |
| US4442296A (en) | 4-Heterocyclic-substituted-2-indanyl alcohols and insecticidal ester derivatives | |
| GB2187457A (en) | Phosphonium salt intermediates for pesticides | |
| KR820002278B1 (ko) | 케톡시이미노에테르 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |