JPH0329776B2 - - Google Patents

Info

Publication number: JPH0329776B2
Authority: JP; Japan
Prior art keywords: methyl; pentene; group; phenoxyphenyl; benzene
Prior art date: 1989-05-18
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

Application number

JP12288789A

Other languages

English (en)

Japanese (ja)

Other versions

JPH029834A (ja

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-05-18

Filing date

1989-05-18

Publication date

1991-04-25

1989-05-18 Application filed filed Critical

1989-05-18 Priority to JP12288789A priority Critical patent/JPH029834A/ja

1990-01-12 Publication of JPH029834A publication Critical patent/JPH029834A/ja

1991-04-25 Publication of JPH0329776B2 publication Critical patent/JPH0329776B2/ja

Status Granted legal-status Critical Current

Links

-1 methylenedioxy group Chemical group 0.000 claims description 37
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004438 haloalkoxy group Chemical group 0.000 claims description 5
125000001188 haloalkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 46
238000003786 synthesis reaction Methods 0.000 description 44
230000015572 biosynthetic process Effects 0.000 description 42
239000000203 mixture Substances 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 22
150000001875 compounds Chemical class 0.000 description 22
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 22
239000002904 solvent Substances 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 16
241000607479 Yersinia pestis Species 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
238000004440 column chromatography Methods 0.000 description 12
239000002917 insecticide Substances 0.000 description 12
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 11
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
241000251468 Actinopterygii Species 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
230000000895 acaricidal effect Effects 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
230000000749 insecticidal effect Effects 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000010410 layer Substances 0.000 description 4
231100000053 low toxicity Toxicity 0.000 description 4
QMMOXUPEWRXHJS-UHFFFAOYSA-N pent-2-ene Chemical class CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000005406 washing Methods 0.000 description 4
JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 description 3
RYPKRALMXUUNKS-UHFFFAOYSA-N 2-Hexene Natural products CCCC=CC RYPKRALMXUUNKS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241001414720 Cicadellidae Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
241000255925 Diptera Species 0.000 description 3
241000238631 Hexapoda Species 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000003513 alkali Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
CUUKIIURFHCYJT-UHFFFAOYSA-N 1-[2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]-3-(trifluoromethyl)benzene Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C)(C)C=CCC(C=1)=CC=CC=1OC1=CC=CC=C1 CUUKIIURFHCYJT-UHFFFAOYSA-N 0.000 description 2
KXRNEATVTIGLBZ-UHFFFAOYSA-N 1-chloro-4-[2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 KXRNEATVTIGLBZ-UHFFFAOYSA-N 0.000 description 2
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
RWNXDEOISAZPHU-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-3-methylbutanal Chemical compound CCOC1=CC=C(C(C)(C)CC=O)C=C1 RWNXDEOISAZPHU-UHFFFAOYSA-N 0.000 description 2
QDKIFIYGNKHERN-UHFFFAOYSA-N 4-(bromomethyl)-1-fluoro-2-phenoxybenzene Chemical compound FC1=CC=C(CBr)C=C1OC1=CC=CC=C1 QDKIFIYGNKHERN-UHFFFAOYSA-N 0.000 description 2
QOZMLWPEWAOZBY-UHFFFAOYSA-N 4-(diethoxyphosphorylmethyl)-1-fluoro-2-phenoxybenzene Chemical compound CCOP(=O)(OCC)CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QOZMLWPEWAOZBY-UHFFFAOYSA-N 0.000 description 2
FEWIGMWODIRUJM-UHFFFAOYSA-N 4-hexen-3-one Chemical compound CCC(=O)C=CC FEWIGMWODIRUJM-UHFFFAOYSA-N 0.000 description 2
WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
SNOYUTZWILESAI-UHFFFAOYSA-N 4-methylpent-1-en-3-one Chemical compound CC(C)C(=O)C=C SNOYUTZWILESAI-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241001674044 Blattodea Species 0.000 description 2
241000336797 Eoeurysa flavocapitata Species 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 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
241000256248 Spodoptera Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
239000000642 acaricide Substances 0.000 description 2
238000007605 air drying Methods 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000000034 method Methods 0.000 description 2
125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000002728 pyrethroid Substances 0.000 description 2
235000009566 rice Nutrition 0.000 description 2
238000005507 spraying Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003860 storage Methods 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
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 1
CEJLIPUOYYASCA-UHFFFAOYSA-N 1-[2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]-3-(trifluoromethyl)benzene Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C)(C)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 CEJLIPUOYYASCA-UHFFFAOYSA-N 0.000 description 1
XOEAHXPADNMWOY-UHFFFAOYSA-N 1-ethoxy-4-(2-methylpentan-2-yl)benzene Chemical compound CCCC(C)(C)C1=CC=C(OCC)C=C1 XOEAHXPADNMWOY-UHFFFAOYSA-N 0.000 description 1
SGMVRYQPBRDBLM-UHFFFAOYSA-N 1-fluoro-4-[4-(4-methoxyphenyl)-4-methylpent-1-enyl]-2-phenoxybenzene Chemical compound C1=CC(OC)=CC=C1C(C)(C)CC=CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 SGMVRYQPBRDBLM-UHFFFAOYSA-N 0.000 description 1
YNEBPLQTZFSKPD-UHFFFAOYSA-N 1-methoxy-4-[2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]benzene Chemical compound C1=CC(OC)=CC=C1C(C)(C)C=CCC1=CC=CC(OC=2C=CC=CC=2)=C1 YNEBPLQTZFSKPD-UHFFFAOYSA-N 0.000 description 1
PDKYRVZAKYOGMJ-UHFFFAOYSA-N 1-methoxy-4-[2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]benzene Chemical compound C1=CC(OC)=CC=C1C(C)(C)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 PDKYRVZAKYOGMJ-UHFFFAOYSA-N 0.000 description 1
SVNWQTGEQPKLNQ-UHFFFAOYSA-N 1-methyl-4-[2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]benzene Chemical compound C1=CC(C)=CC=C1C(C)(C)C=CCC1=CC=CC(OC=2C=CC=CC=2)=C1 SVNWQTGEQPKLNQ-UHFFFAOYSA-N 0.000 description 1
FEPOSPSDTBOWLY-UHFFFAOYSA-N 1-methyl-4-[2-methyl-5-(3-phenoxyphenyl)pent-4-en-2-yl]benzene Chemical compound C1=CC(C)=CC=C1C(C)(C)CC=CC1=CC=CC(OC=2C=CC=CC=2)=C1 FEPOSPSDTBOWLY-UHFFFAOYSA-N 0.000 description 1
VBSHDPOAIAJYMV-UHFFFAOYSA-N 1-methyl-4-[2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]benzene Chemical compound C1=CC(C)=CC=C1C(C)(C)CCCC1=CC=CC(OC=2C=CC=CC=2)=C1 VBSHDPOAIAJYMV-UHFFFAOYSA-N 0.000 description 1
YNXOMDRPWQMDQL-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-methylpropanal Chemical compound O=CC(C)(C)C1=CC=C(Cl)C=C1 YNXOMDRPWQMDQL-UHFFFAOYSA-N 0.000 description 1
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
VOPXNVSDUXSSEE-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)C1=CC=C2OCOC2=C1 VOPXNVSDUXSSEE-UHFFFAOYSA-N 0.000 description 1
BVYURCFIUPFFDK-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)C1=CC=C(Cl)C=C1 BVYURCFIUPFFDK-UHFFFAOYSA-N 0.000 description 1
JPOPBFXQDOKVGJ-UHFFFAOYSA-N 3-(4-ethoxyphenyl)-3-methylbutan-2-one Chemical compound CCOC1=CC=C(C(C)(C)C(C)=O)C=C1 JPOPBFXQDOKVGJ-UHFFFAOYSA-N 0.000 description 1
ZIYLSBHBLCBTJB-UHFFFAOYSA-N 3-methyl-3-(4-methylphenyl)butan-2-one Chemical compound CC(=O)C(C)(C)C1=CC=C(C)C=C1 ZIYLSBHBLCBTJB-UHFFFAOYSA-N 0.000 description 1
RJSKVGQJZQDFQI-UHFFFAOYSA-N 3-methyl-3-[3-(trifluoromethyl)phenyl]butan-2-one Chemical compound CC(=O)C(C)(C)C1=CC=CC(C(F)(F)F)=C1 RJSKVGQJZQDFQI-UHFFFAOYSA-N 0.000 description 1
BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 description 1
NWOQMCFVOCINBU-UHFFFAOYSA-N 4-(4-methoxyphenyl)-3-methylbutan-2-one Chemical compound COC1=CC=C(CC(C)C(C)=O)C=C1 NWOQMCFVOCINBU-UHFFFAOYSA-N 0.000 description 1
PHQMXSMKIFCJEO-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-methyl-1-(3-phenoxyphenyl)pent-1-en-3-one Chemical compound C1=CC(OC)=CC=C1C(C)(C)C(=O)C=CC1=CC=CC(OC=2C=CC=CC=2)=C1 PHQMXSMKIFCJEO-UHFFFAOYSA-N 0.000 description 1
DOJJRMAPFAFRKS-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-4-methylpent-1-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C)CC=CC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 DOJJRMAPFAFRKS-UHFFFAOYSA-N 0.000 description 1
RMANJNOQEVINPB-UHFFFAOYSA-N 4-[4-(4-ethoxyphenyl)-4-methylpent-2-enyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(OCC)=CC=C1C(C)(C)C=CCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 RMANJNOQEVINPB-UHFFFAOYSA-N 0.000 description 1
JDICMOLUAHZVDS-UHFFFAOYSA-N 4-fluoro-3-phenoxybenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1OC1=CC=CC=C1 JDICMOLUAHZVDS-UHFFFAOYSA-N 0.000 description 1
WYVCRYKTWRUNAP-UHFFFAOYSA-N 4-methyl-1-(3-phenoxyphenyl)-4-[3-(trifluoromethyl)phenyl]pent-1-en-3-one Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(C)(C)C(=O)C=CC(C=1)=CC=CC=1OC1=CC=CC=C1 WYVCRYKTWRUNAP-UHFFFAOYSA-N 0.000 description 1
JQTJAMXNMIMRDL-UHFFFAOYSA-N 4-methyl-1-(4-methylphenyl)pent-1-en-3-one Chemical compound CC(C)C(=O)C=CC1=CC=C(C)C=C1 JQTJAMXNMIMRDL-UHFFFAOYSA-N 0.000 description 1
CJJLBRCHLVJFEK-UHFFFAOYSA-N 5-[2-methyl-5-(3-phenoxyphenyl)pent-3-en-2-yl]-1,3-benzodioxole Chemical compound C=1C=C2OCOC2=CC=1C(C)(C)C=CCC(C=1)=CC=CC=1OC1=CC=CC=C1 CJJLBRCHLVJFEK-UHFFFAOYSA-N 0.000 description 1
HZHONNGEEREBEP-UHFFFAOYSA-N 5-[2-methyl-5-(3-phenoxyphenyl)pentan-2-yl]-1,3-benzodioxole Chemical compound C=1C=C2OCOC2=CC=1C(C)(C)CCCC(C=1)=CC=CC=1OC1=CC=CC=C1 HZHONNGEEREBEP-UHFFFAOYSA-N 0.000 description 1
241000238876 Acari Species 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
244000291564 Allium cepa Species 0.000 description 1
235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241001425390 Aphis fabae Species 0.000 description 1
241000238657 Blattella germanica Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
241001466042 Fulgoromorpha Species 0.000 description 1
241000237858 Gastropoda Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
244000017020 Ipomoea batatas Species 0.000 description 1
235000002678 Ipomoea batatas Nutrition 0.000 description 1
241000406668 Loxodonta cyclotis Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
239000005916 Methomyl Substances 0.000 description 1
240000001307 Myosotis scorpioides Species 0.000 description 1
241001477931 Mythimna unipuncta Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241001674048 Phthiraptera Species 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
241000500441 Plutellidae Species 0.000 description 1
241000208292 Solanaceae Species 0.000 description 1
241001454295 Tetranychidae Species 0.000 description 1
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 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 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
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003945 anionic surfactant Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 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
235000014121 butter Nutrition 0.000 description 1
239000000073 carbamate insecticide Substances 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 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
230000000052 comparative effect Effects 0.000 description 1
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
238000007599 discharging Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000011010 flushing procedure Methods 0.000 description 1
239000003292 glue Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
230000001846 repelling effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
JQPMDTQDAXRDGS-UHFFFAOYSA-N triphenylalumane Chemical compound C1=CC=CC=C1[Al](C=1C=CC=CC=1)C1=CC=CC=C1 JQPMDTQDAXRDGS-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Landscapes

Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP12288789A 1989-05-18 1989-05-18 新規芳香族アルケン化合物 Granted JPH029834A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP12288789A JPH029834A (ja)	1989-05-18	1989-05-18	新規芳香族アルケン化合物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP12288789A JPH029834A (ja)	1989-05-18	1989-05-18	新規芳香族アルケン化合物

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57082473A Division JPS58201737A (ja)	1982-05-18	1982-05-18	新規芳香族アルカン誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤

Publications (2)

Publication Number	Publication Date
JPH029834A JPH029834A (ja)	1990-01-12
JPH0329776B2 true JPH0329776B2 (cs)	1991-04-25

Family

ID=14847094

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP12288789A Granted JPH029834A (ja)	1989-05-18	1989-05-18	新規芳香族アルケン化合物

Country Status (1)

Country	Link
JP (1)	JPH029834A (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0499590A (ja) *	1990-12-27	1992-03-31	Hitachi Ltd	洗たく機

1989
- 1989-05-18 JP JP12288789A patent/JPH029834A/ja active Granted

Also Published As

Publication number	Publication date
JPH029834A (ja)	1990-01-12

Publication	Publication Date	Title
US4176189A (en)	1979-11-27	Insecticidal and acaricidal hydantoin N-methylol esters
US4336194A (en)	1982-06-22	Benzyl pyrrolyl methyl carboxylate insecticides and acaricides
US3973036A (en)	1976-08-03	Cyclopropanecarboxylic acid esters
US4327109A (en)	1982-04-27	Novel alkadienylcyclopropanecarboxylates
KR870001463B1 (ko)	1987-08-12	방향족 알칸 유도체의 제조 방법
JP3895795B2 (ja)	2007-03-22	殺菌・殺カビ方法、化合物およびベンゾフエノン含有組成物
US4003945A (en)	1977-01-18	Novel cyclopropanecarboxylates
FR2491924A1 (fr)	1982-04-16	Nouveaux ethers-oxydes et sulfures aryl-2 ethyliques, procede de leur preparation, agents insecticides et acaricides les contenant et procede de lutte contre les insectes et les acariens utilisant ces nouveaux composes
HU189506B (en)	1986-07-28	Insecticides and acaricides containing as reagent derivatives of new aril-propyl-ether or thioether and process for production of the reagent
US3981903A (en)	1976-09-21	Cyclopropane carboxylic acid esters
KR0140208B1 (ko)	1998-06-01	살충, 살비활성의 피리다지논
US4263463A (en)	1981-04-21	Acetylenic secondary alcohols
JPH0848682A (ja)	1996-02-20	殺虫性テトラヒドロフラン系化合物
JP2704655B2 (ja)	1998-01-26	３一置換フェニルピラゾール誘導体又はその塩類及び除草剤
JPH04288069A (ja)	1992-10-13	新規なベンゾフラン誘導体、その製造法、得られる新規な中間体及びその有害生物防除剤としての用途
JPS6157300B2 (cs)	1986-12-06
US4053625A (en)	1977-10-11	Insecticides
JPH0639430B2 (ja)	1994-05-25	炭化水素系化合物およびそれを有効成分とする殺虫、殺ダニ剤
WO2003062222A1 (en)	2003-07-31	Pyrazolecarboxamides, intermediates thereof and pesticides containing the same as the active ingredient
JPH0329776B2 (cs)	1991-04-25
US4327094A (en)	1982-04-27	Insecticidal and acaricidal 3,5-dioxo-2,3,4,5-triazine compounds
JPS6030301B2 (ja)	1985-07-16	シクロプロパンカルボン酸３−（２，２−ジクロロビニルオキシ）ベンジルエステル、その製造方法及び該化合物を含有する殺虫、殺ダニ剤
JP4004555B2 (ja)	2007-11-07	殺虫化合物
JPH0465805B2 (cs)	1992-10-21
JPS5855402A (ja)	1983-04-01	殺虫殺ダニ組成物