JPH0231682B2 - - Google Patents
Info
- Publication number
- JPH0231682B2 JPH0231682B2 JP56162793A JP16279381A JPH0231682B2 JP H0231682 B2 JPH0231682 B2 JP H0231682B2 JP 56162793 A JP56162793 A JP 56162793A JP 16279381 A JP16279381 A JP 16279381A JP H0231682 B2 JPH0231682 B2 JP H0231682B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- ether
- fluorobenzyl
- thioether
- toluene
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 claims description 58
- 150000003568 thioethers Chemical class 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
- -1 methylenedioxy group Chemical group 0.000 claims description 17
- 230000000895 acaricidal effect Effects 0.000 claims description 14
- 230000000749 insecticidal effect Effects 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 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 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001624 naphthyl group Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 89
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 84
- 150000001875 compounds Chemical class 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 238000003786 synthesis reaction Methods 0.000 description 17
- 238000009472 formulation Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 241000607479 Yersinia pestis Species 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000002917 insecticide Substances 0.000 description 12
- 239000010446 mirabilite Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000642 acaricide Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 241000255925 Diptera Species 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- 238000004440 column chromatography Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- NJTICDHSNUXDFF-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-methylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=C(Cl)C=C1 NJTICDHSNUXDFF-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- JFGYWWUCPQBFAF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C2OCOC2=C1 JFGYWWUCPQBFAF-UHFFFAOYSA-N 0.000 description 3
- RKFZFWKPMXSTJD-UHFFFAOYSA-N 4-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-1-fluoro-2-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 RKFZFWKPMXSTJD-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 3
- 241001414720 Cicadellidae Species 0.000 description 3
- 241000254173 Coleoptera Species 0.000 description 3
- 241000257226 Muscidae Species 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- 241000254152 Sitophilus oryzae Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000003912 environmental pollution Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- SBOXLEYOAFOTAY-UHFFFAOYSA-N 1-chloro-2-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-4-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C(=CC=1)Cl)=CC=1OC1=CC=CC=C1 SBOXLEYOAFOTAY-UHFFFAOYSA-N 0.000 description 2
- FKBIRPXIZSRYDA-UHFFFAOYSA-N 1-chloro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]propan-2-yl]benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 FKBIRPXIZSRYDA-UHFFFAOYSA-N 0.000 description 2
- XRTANKYQJQXSFP-UHFFFAOYSA-N 1-tert-butyl-4-chlorobenzene Chemical compound CC(C)(C)C1=CC=C(Cl)C=C1 XRTANKYQJQXSFP-UHFFFAOYSA-N 0.000 description 2
- PPGNSVHWVIRQLC-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-2-methylpropan-1-ol Chemical compound OCC(C)(C)C1=CC=C2OCOC2=C1 PPGNSVHWVIRQLC-UHFFFAOYSA-N 0.000 description 2
- OSGPUJRJFJWBCZ-UHFFFAOYSA-N 2-(4-bromophenoxy)-4-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-1-fluorobenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C=1)=CC=C(F)C=1OC1=CC=C(Br)C=C1 OSGPUJRJFJWBCZ-UHFFFAOYSA-N 0.000 description 2
- RXPLTFIXDGQRFS-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-methylbutanenitrile Chemical compound CCC(C)(C#N)C1=CC=C(F)C=C1 RXPLTFIXDGQRFS-UHFFFAOYSA-N 0.000 description 2
- LDLOCBUXFIOXFH-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-methylbutanoic acid Chemical compound CCC(C)(C(O)=O)C1=CC=C(F)C=C1 LDLOCBUXFIOXFH-UHFFFAOYSA-N 0.000 description 2
- JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 2
- JPTHCYFZRSLQMW-UHFFFAOYSA-N 2-(4-fluorophenyl)propanenitrile Chemical compound N#CC(C)C1=CC=C(F)C=C1 JPTHCYFZRSLQMW-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 241001313742 Callosobruchus chinensis Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000256054 Culex <genus> Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001466042 Fulgoromorpha Species 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 241000238814 Orthoptera Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000718000 Pulex irritans Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000000073 carbamate insecticide Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000005485 electric heating Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 238000003958 fumigation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UFXDRIJUGWOQTP-UHFFFAOYSA-N (4-fluoro-3-phenoxyphenyl)methanol Chemical compound OCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 UFXDRIJUGWOQTP-UHFFFAOYSA-N 0.000 description 1
- LGAQJENWWYGFSN-PLNGDYQASA-N (z)-4-methylpent-2-ene Chemical compound C\C=C/C(C)C LGAQJENWWYGFSN-PLNGDYQASA-N 0.000 description 1
- HRNYAXZRLJSBLE-UHFFFAOYSA-N 1,2-dibromo-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]butan-2-yl]benzene Chemical compound C=1C=C(Br)C(Br)=CC=1C(C)(CC)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 HRNYAXZRLJSBLE-UHFFFAOYSA-N 0.000 description 1
- CCLZIXBQQIVOFN-UHFFFAOYSA-N 1,2-dichloro-4-[1-[(4-fluoro-3-phenoxyphenyl)methoxy]-2-methylpropan-2-yl]benzene Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)COCC(C=1)=CC=C(F)C=1OC1=CC=CC=C1 CCLZIXBQQIVOFN-UHFFFAOYSA-N 0.000 description 1
- LCDAGMASCMWFIY-UHFFFAOYSA-N 1,2-dichloro-4-[1-[[4-fluoro-3-(4-fluorophenoxy)phenyl]methoxy]-2-methylbutan-2-yl]benzene Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(CC)COCC(C=1)=CC=C(F)C=1OC1=CC=C(F)C=C1 LCDAGMASCMWFIY-UHFFFAOYSA-N 0.000 description 1
- FFWZKOHRALZIQN-UHFFFAOYSA-N 1,2-dichloro-4-[1-[[4-fluoro-3-(4-fluorophenoxy)phenyl]methoxy]-2-methylpropan-2-yl]benzene Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)COCC(C=1)=CC=C(F)C=1OC1=CC=C(F)C=C1 FFWZKOHRALZIQN-UHFFFAOYSA-N 0.000 description 1
- UPXSOQYAYJCLOD-UHFFFAOYSA-N 1,2-dichloro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]butan-2-yl]benzene Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(CC)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 UPXSOQYAYJCLOD-UHFFFAOYSA-N 0.000 description 1
- WJUQMVUSEWHQQA-UHFFFAOYSA-N 1,2-dichloro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]propan-2-yl]benzene Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WJUQMVUSEWHQQA-UHFFFAOYSA-N 0.000 description 1
- RAEMVYWYJVFTIF-UHFFFAOYSA-N 1,2-difluoro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]butan-2-yl]benzene Chemical compound C=1C=C(F)C(F)=CC=1C(C)(CC)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 RAEMVYWYJVFTIF-UHFFFAOYSA-N 0.000 description 1
- WSJDUYCVDVCTEY-UHFFFAOYSA-N 1,2-difluoro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]propan-2-yl]benzene Chemical compound C=1C=C(F)C(F)=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WSJDUYCVDVCTEY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NVNPLEPBDPJYRZ-UHFFFAOYSA-N 1-(bromomethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CBr)C=C1 NVNPLEPBDPJYRZ-UHFFFAOYSA-N 0.000 description 1
- LQYOQVLEODMGBX-UHFFFAOYSA-N 1-(difluoromethoxy)-4-[4-[4-(difluoromethoxy)phenyl]-2-methylpent-3-en-2-yl]benzene Chemical compound C=1C=C(OC(F)F)C=CC=1C(C)=CC(C)(C)C1=CC=C(OC(F)F)C=C1 LQYOQVLEODMGBX-UHFFFAOYSA-N 0.000 description 1
- UYGVUVDQOKNLSW-UHFFFAOYSA-N 1-[[2-(3-chloro-4-methoxyphenyl)-2-methylpropoxy]methyl]-3-fluoro-5-(3-fluorophenoxy)benzene Chemical compound C1=C(Cl)C(OC)=CC=C1C(C)(C)COCC1=CC(F)=CC(OC=2C=C(F)C=CC=2)=C1 UYGVUVDQOKNLSW-UHFFFAOYSA-N 0.000 description 1
- HMMFVEHQYXVXPS-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-3-fluoro-5-(4-fluorophenoxy)benzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C=1)=CC(F)=CC=1OC1=CC=C(F)C=C1 HMMFVEHQYXVXPS-UHFFFAOYSA-N 0.000 description 1
- CZJOQTUIXWPSGD-UHFFFAOYSA-N 1-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-3-fluoro-5-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C=1)=CC(F)=CC=1OC1=CC=CC=C1 CZJOQTUIXWPSGD-UHFFFAOYSA-N 0.000 description 1
- DCEYDROJSWIFOB-UHFFFAOYSA-N 1-bromo-2-[[2-(4-chlorophenyl)-2-methylpropoxy]methyl]-4-phenoxybenzene Chemical compound C=1C=C(Cl)C=CC=1C(C)(C)COCC(C(=CC=1)Br)=CC=1OC1=CC=CC=C1 DCEYDROJSWIFOB-UHFFFAOYSA-N 0.000 description 1
- PNJFLQLZXPNLDU-UHFFFAOYSA-N 1-bromo-2-[[2-methyl-2-(4-methylphenyl)propoxy]methyl]-4-phenoxybenzene Chemical compound C1=CC(C)=CC=C1C(C)(C)COCC1=CC(OC=2C=CC=CC=2)=CC=C1Br PNJFLQLZXPNLDU-UHFFFAOYSA-N 0.000 description 1
- WALIQCRJFFZXNP-UHFFFAOYSA-N 1-bromo-2-chloro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]butan-2-yl]benzene Chemical compound C=1C=C(Br)C(Cl)=CC=1C(C)(CC)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 WALIQCRJFFZXNP-UHFFFAOYSA-N 0.000 description 1
- FJCOAJYKSRQCJV-UHFFFAOYSA-N 1-bromo-2-chloro-4-[2-methyl-1-[(3-phenoxyphenyl)methoxy]propan-2-yl]benzene Chemical compound C=1C=C(Br)C(Cl)=CC=1C(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 FJCOAJYKSRQCJV-UHFFFAOYSA-N 0.000 description 1
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- 244000013123 dwarf bean Species 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000003915 liquefied petroleum gas Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003900 soil pollution Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- NBRKLOOSMBRFMH-UHFFFAOYSA-N tert-butyl chloride Chemical compound CC(C)(C)Cl NBRKLOOSMBRFMH-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Description
本発明は下記の一般式〔〕
〔式中、Arは低級アルキル置換ナフチル基、非
置換フエニル基又は４−位がハロゲン原子、低級
アルキル基、低級ハロアルキル基、低級アルコキ
シ基、低級ハロアルコキシ基、低級アルキルチオ
基、シアノ基又はニトロ基で置換されたフエニル
基、４−位の外に更に３−位がハロゲン原子、低
級アルキル基又は低級アルコキシ基で置換された
フエニル基もしくはメチレンジオキシ基で置換さ
れたフエニル基を、R1はメチル基またはエチル
基を、R2はメチル基、エチル基またはイソプロ
ピル基を、R3は水素原子、ハロゲン原子を、R4
は水素原子、ハロゲン原子、炭素数１ないし２の
低級アルキル基または炭素数１ないし２の低級ア
ルコキシ基をそれぞれ表わす。Ｙは酸素原子また
は硫黄原子を表わす〕で表わされる２−アリール
エチルエーテル誘導体またはチオエーテル誘導体
の１種または２種以上と次に示す化合物、オクタ
クロロジプロピルエーテル（以下、Ｓ−421と略
す）
を含有している殺虫殺虫ダニ剤組成物に関するも
のである。
一般に農薬（殺虫剤、殺菌剤、除草剤等）は経
済性と環境汚染の問題から使用場面においてでき
る限り使用量を少なくすることが、要求されてい
る。
従来、防疫用の殺虫殺ダニ剤としては主とし
て、ピレスロイド系、有機リン系の薬剤が使用さ
れ、農園芸用には主に有機リン系、又はカーバメ
ート系の各種薬剤が用いられてきたが、これらの
殺虫剤殺ダニ剤は、速効性、浸透移行性、ガス効
果など、すぐれた特性をもつものがあるが、殺虫
スペクトル、残効性、魚毒性、人蓄毒性などの点
ですべてに満足いくものではない。更に、これら
の薬剤が長年にわたつて使用された結果、これら
の殺虫剤に対して、強い抵抗性を示す害虫が、各
地に出現してきた。水稲害虫のウンカ・ヨコバイ
類、野菜害虫のコナガ、衛生害虫であるイエバ
エ、各種作物に害を与えるハダニ類などは特に薬
剤抵抗性の発達が著しく、これらの害虫に対して
は、上記の有機リン系殺虫剤、カーバメート系殺
虫剤は実用性を失ないつつある。更に、これらの
薬剤の多量に田畑に投入することによる、土壤、
河川などの環境汚染も問題となり、低薬量での防
除が望まれている。
本発明の前記一般式〔〕で表わされる新規化
合物は、これらの要求を満たす条件を備え、単独
でも殺虫、殺ダニ活性を有するが、本発明者らは
さらに、これらの化合物の実際場面でのすぐれた
防除効果と使用量の減少のために種々の検討を重
ねた結果、一般式〔〕で示される化合物と、協
力の１種または２種以上とを混合施用することに
より、単独で施用する場合に比較して、殺虫スペ
クトルが拡がり、殺虫活性が相乗的に強化される
ことを見い出して本発明を完成した。
次に本発明の前記一般式〔〕で示される化合
物の代表例とそれらの物性を下記第１表に示す。
The present invention is based on the following general formula [] [In the formula, Ar is a lower alkyl-substituted naphthyl group, an unsubstituted phenyl group, a halogen atom at the 4-position, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group, a cyano group, or a nitro group. R 1 is a phenyl group substituted with a phenyl group substituted with a halogen atom, a lower alkyl group, or a lower alkoxy group at the 3-position in addition to the 4-position, or a phenyl group substituted with a methylenedioxy group. Methyl group or ethyl group, R 2 is methyl group, ethyl group or isopropyl group, R 3 is hydrogen atom, halogen atom, R 4
represents a hydrogen atom, a halogen atom, a lower alkyl group having 1 to 2 carbon atoms, or a lower alkoxy group having 1 to 2 carbon atoms, respectively. One or more 2-arylethyl ether derivatives or thioether derivatives represented by [Y represents an oxygen atom or a sulfur atom] and the following compound, octachlorodipropyl ether (hereinafter abbreviated as S-421) The present invention relates to an insecticidal and acaricidal composition containing the following. Generally, agricultural chemicals (insecticides, fungicides, herbicides, etc.) are required to be used in as little amount as possible due to economic efficiency and environmental pollution issues. Conventionally, pyrethroids and organophosphorus-based agents have been mainly used as insecticides and acaricides for epidemic prevention, and various organic phosphorus-based or carbamate-based agents have been used for agricultural and horticultural purposes. Some insecticides and acaricides have excellent properties such as fast-acting, systemic migration, and gas effect, but none are satisfactory in terms of insecticidal spectrum, residual effectiveness, fish toxicity, and human toxicity. It's not a thing. Furthermore, as a result of the long-term use of these insecticides, pest insects that exhibit strong resistance to these insecticides have appeared in various places. Planthoppers and leafhoppers that are rice pests, diamondback moths that are vegetable pests, house flies that are sanitary pests, and spider mites that damage various crops are particularly susceptible to drug resistance. Carbamate-based insecticides and carbamate-based insecticides are losing their practicality. Furthermore, by introducing large amounts of these chemicals into the fields, soil pollution,
Environmental pollution of rivers and other areas is also a problem, and control using low doses of chemicals is desired. The novel compounds of the present invention represented by the above general formula [] satisfy these requirements and have insecticidal and acaricidal activity even on their own, but the present inventors have further investigated the actual use of these compounds. As a result of various studies in order to achieve excellent control effects and reduce the amount used, we found that the compound represented by the general formula [] and one or more of the following compounds can be applied in combination, or applied alone. The present invention was completed based on the discovery that the insecticidal spectrum is broadened and the insecticidal activity is synergistically enhanced compared to the conventional method. Next, representative examples of the compounds represented by the general formula [] of the present invention and their physical properties are shown in Table 1 below.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
前記一般式（）で表わされる化合物は新規化
合物であり、その合成例を示すと以下のごとくで
ある。一般式〔〕で表わされる化合物は一般式
〔〕
で表わされる化合物を一般式〔〕
〔これらの式中、Ar、R1、R2、R3、R4はそれぞ
れ前記の意味を表わし、基Ａおよび基Ｂはその一
方の基がハロゲン原子を表わし、他方の基がＸ−
Ｍ基（この式でＸは前記の意味を表わし、Ｍは水
素原子、アルカリ金属原子またはアルカリ土類金
属原子を表わす）を表わすか、または共にヒドロ
キシル基を表わす〕で表わされる化合物と反応さ
せることによつて得られる。
次にこのようにして得られる本発明化合物の代
表例を示すが、勿論本発明化合物がこれら例示の
みに限定されるものではない。
なお、本発明化合物には、一般式〔〕におい
て、R1とR2が異なる基である場合には不整炭素
を有し、光学異性体が存在するが、これら光学異
性体およびこれら成分の混合物を包含している。
３−（４−フルオロフエノキシ）−４−フルオロ
ベンジル ２−（４−クロロフエニル）−２−メチ
ルプロピルエーテルおよびチオエーテル、３−フ
エノキシ−４−フルオロベンジル ２−フエニル
−２−メチルプロピルエーテルおよびチオエーテ
ル、３−フエノキシ−４−クロロベンジル ２−
（４−クロロフエニル）−２−メチルプロピルエー
テルおよびチオエーテル、３−フエノキシ−４−
フルオロベンジル ２−（４−メトキシフエニル）
−２−メチルプロピルエーテルおよびチオエーテ
ル、３−（４−フルオロフエノキシ）−４−フルオ
ロベンジル ２−（４−メトキシフエニル）−２−
メチルプロピルエーテルおよびチオエーテル、３
−フエノキシ−４−フルオロベンジル ２−（４
−クロロフエニル）−２−エチルブチルエーテル
およびチオエーテル、３−フエノキシ−６−クロ
ロベンジル ２−（４−クロロフエニル）−２−メ
チルプロピルエーテルおよびチオエーテル、３−
（４−フルオロフエノキシ）−４−フルオロベンジ
ル ２−（３，４−ジクロロフエニル）−２−メチ
ルブチルエーテルおよびチオエーテル
３−フエノキシ−４−フルオロベンジル ２−
（４−クロロフエニル）−２−メチルプロピルエー
テルおよびチオエーテル、３−（２−フルオロフ
エノキシ）−４−フルオロベンジル ２−（３，４
−ジクロロフエニル）−２−メチルプロピルエー
テルおよびチオエーテル、３−（２−フルオロフ
エノキシ）−４−フルオロベンジル ２−（４−ク
ロロフエニル）−２−メチルプロピルエーテルお
よびチオエーテル、３−フエノキシ−４−フルオ
ロベンジル ２−（２−ナフタレン−２−イル）−
２−メチルプロピルエーテルおよびチオエーテ
ル、３−（４−メトキシフエノキシ）−４−フルオ
ロベンジル ２−（４−クロロフエニル）−２−メ
チルプロピルエーテルおよびチオエーテル、３−
フエノキシ−４−フルオロベンジル ２−（３，
４−ジクロロフエニル）−２−メチルプロピルエ
ーテルおよびチオエーテル、３−（４−ブロモフ
エノキシ）−４−フルオロベンジル ２−（４−ク
ロロフエニル）−２−メチルプロピルエーテルお
よびチオエーテル、３−フエノキシ−４−フルオ
ロベンジル ２−（４−ブロモフエニル）−２−メ
チルプロピルエーテルおよびチオエーテル、３−
フエノキシ−４−フルオロベンジル ２−（３−
エトキシ−４−ブロモフエニル）−２−メチルプ
ロピルエーテルおよびチオエーテル、３−フエノ
キシ−４−フルオロベンジル ２−（４−クロロ
フエニル）−２−メチルブチルエーテルおよびチ
オエーテル、３−フエノキシ−４−フルオロベン
ジル ２−（４−ジフルオロメトキシフエニル）−
２−メチルプロピルエーテルおよびチオエーテ
ル、３−（３−メチルフエノキシ）−４−フルオロ
ベンジル ２−（４−クロロフエニル）−２−メチ
ルプロピルエーテルおよびチオエーテル、３−
（２−フルオロフエノキシ）−４−フルオロベンジ
ル ２−（４−メチルチオフエニル）−２−メチル
プロピルエーテルおよびチオエーテル、３−（３
−フルオロフエノキシ）−５−フルオロベンジル
２−（３−クロロ−４−メトキシフエニル）−２
−メチルプロピルエーテルおよびチオエーテル、
３−フエノキシ−６−ブロモベンジル ２−（４
−メチルフエニル）−２−メチルプロピルエーテ
ルおよびチオエーテル、３−（４−フルオロフエ
ノキシ）−４−フルオロベンジル ２−（３，４−
ジクロロフエニル）−２−メチルプロピルエーテ
ルおよびチオエーテル、３−フエノキシ−２−フ
ルオロベンジル２−フエニル−２−メチルプロピ
ルエーテルおよびチオエーテル、３−フエノキシ
−４−フルオロベンジル ２−（４−クロロフエ
ニル）−２，３−ジメチルブチルエーテルおよび
チオエーテル、３−フエノキシ−６−ブロモベン
ジル ２−（４−クロロフエニル）−２−メチルプ
ロピルエーテルおよびチオエーテル、３−（４−
フルオロフエノキシ）−２−フルオロベンジル
２−フエニル−２−メチルプロピルエーテルおよ
びチオエーテル、３−（４−フルオロフエノキシ）
−５−フルオロベンジル ２−（４−クロロフエ
ニル）−２−メチルプロピルエーテルおよびチオ
エーテル、３−フエノキシ−４−フルオロベンジ
ル ２−（４−フルオロフエニル）−２−メチルプ
ロピルエーテルおよびチオエーテル、３−フエノ
キシ−５−フルオロベンジル２−（４−クロロフ
エニル）−２−メチルプロピルエーテルおよびチ
オエーテル、３−フエノキシ−４−フルオロベン
ジル ２−（４−ニトロフエニル）−２−メチルプ
ロピルエーテルおよびチオエーテル、３−フエノ
キシ−５−クロロベンジル ２−（４−クロロフ
エニル）−２−メチルプロピルエーテルおよびチ
オエーテル、３−フエノキシ−４−フルオロベン
ジル ２−（３，４−メチレンジオキシフエニル）
−２−メチルプロピルエーテルおよびチオエーテ
ル、
３−フエノキシベンジル２−（４−ブロモフエ
ニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（３，４−ジブロ
モフエニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（４−クロロフエ
ニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（４−クロロフエ
ニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（３−ブロモ−４
−クロロフエニル）−２−エチルプロピルエーテ
ル、３−フエノキシベンジル２−（３，４−ジク
ロロフエニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（４−ブロモフエ
ニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（４−フロロフエ
ニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（３−クロロ−４
−フロロフエニル）−２−エチルプロピルエーテ
ル、
３−フエノキシベンジル２−（３，４−ジクロ
ロフエニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（３−ブロモ−４
−クロロフエニル）−２−メチルプロピルエーテ
ル、３−フエノキシベンジル２−（３，４−ジブ
ロモフエニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（４−クロロフエ
ニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（４−メチルフエ
ニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（３−クロロ−４
−フロロフエニル）−２−メチルプロピルエーテ
ル、
３−フエノキシベンジル２−（３，４−ジフロ
ロフエニル）−２−メチルプロピルエーテル、
３−フエノキシベンジル２−（３，４−ジフロ
ロフエニル）−２−エチルプロピルエーテル、
３−フエノキシベンジル２−（３−ブロモ−４
−フロロフエニル）−２−メチルプロピルエーテ
ル、
３−フエノキシベンジル２−（３−ブロモ−４
−フロロフエニル）−２−エチルプロピルエーテ
ル、
３−フエノキシベンジル２−（３−フロロ−４
−ブロモフエニル）−２−メチルプロピルエーテ
ル、
３−フエノキシベンジル２−（３−フロロ−４
−ブロモフエニル）−２−エチルプロピルエーテ
ル、
３−フエノキシベンジル２−（４−ブロモ−３
−クロロフエニル）−２−メチルプロピルエーテ
ル、
３−フエノキシベンジル２−（４−ブロモ−３
−クロロ−フエニル）−２−エチルプロピルエー
テル、
等があげられる。次に本発明の前記一般式〔〕
で示される化合物の製造法について合成実施例を
あげてさらに詳細に説明する。
合成実施例 １
３−（４−ブロモフエノキシ）−４−フルオロベ
ンジル ２−（４−クロロフエニル）−２−メチ
ルプロピルエーテル
乾燥アセトニトリル20mlに水素化ナトリウム
（60％in oil）0.9ｇを加え、次いで２−（４−クロ
ロフエニル）−２−メチルプロピルアルコール2.8
ｇ／10mlアセトニトリル溶液を50℃で滴下した。
30分間加熱還流したのち、３−（４−ブロモフ
エノキシ）−４−フルオロベンジルプロマイド6.6
ｇ／10mlアセトニトリル溶液を10分間で滴下し、
さらに、１時間加熱還流した。室温まで冷却後、
水に排出し、トルエンにて抽出した。トルエン抽
出液を飽和食塩水にて洗浄後、芒硝にて乾燥し
た。減圧下にトルエンを留去して得られた粗エー
テルをシリカゲル150ｇのカラムクロマトグラフ
イー（展開溶媒：トルエン／ｎ−ヘキサン１：
１）により精製し目的としたエーテル4.6ｇ（理
論収率65％）を得た。
n20 D 1.5806
νfilm nax 1590、1490、1435、1295、1225、1105、
1020、830cm-1
δccl4 1.29（Ｓ、6H）、3.32（Ｓ、2H）、4.32（Ｓ、
2H）、6.7〜7.5（ｍ、11H）
分析結果
C23H21BrClFO2
計算値（％） Ｃ 59.56 Ｈ 4.56
Br 17.23 Cl 7.65 Ｆ 4.10
実測値（％） Ｃ 59.85 Ｈ 4.64
Br 17.01 Cl 7.77 Ｆ 4.00
合成実施例 ２
３−フエノキシ−４−フルオロベンジル ２−
（４−メチルフエニル）−メチルプロピルエーテ
ル
トルエン20mlに水素化ナトリウム（60％in
oil）0.63ｇを加熱還流し、これに２−（４−メチ
ルフエニル）−２−メチルプロピルアルコール1.7
ｇ／25％DMF−トルエン10ml溶液を15分間で滴
下した。このまゝ10分間撹拌を続けたのち、３−
フエノキシ−４−フルオロロベンジルクロライド
3.0ｇ／トルエン10ml溶液を20分間で滴下した。
さらに、1.5時間加熱還流したのち、室温まで冷
却し、水に排出した。
トルエンにて抽出液を水洗したのち、芒硝で乾
燥した。減圧下にトルエンを留去して得られた粗
エーテルをシリカゲルカラム100ｇのカラムクロ
マトグラフイー（展開溶媒：トルエン／ｎ−ヘキ
サン１：１）により精製し目的とした精エーテル
2.7ｇ（理論収率71％）を得た。
n20 D 1.5611
νfilm nax 1600、1500、1435、1290、1225、1105、
825、695cm-1
δccl4 1.30（Ｓ、6H）、2.27（Ｓ、3H）、3.34（Ｓ、
2H）、4.34（Ｓ、2H）、6.8〜7.4（ｍ、12H）
分析結果
C24H25FO2
計算値（％） Ｃ 79.09 Ｈ 6.91 Ｆ 5.21
実測値（％） Ｃ 79.23 Ｈ 7.01 Ｆ 5.42
合成実施例 ３
３−フエノキシ−４−フルオロベンジル ２−
（４−クロロフエニル）−２−メチルプロピルエ
ーテル
50％NaOH水溶液20ｇ、２−（４−クロロフエ
ニル）−２−メチルプロピルアルコール6.0ｇ、３
−フエノキシ−４−フルオロベンジルブロマイド
8.6ｇ、およびテトラブチルアンモニウムブロマ
イド1.1ｇを加え、80℃に１時間加熱撹拌した。
室温まで冷却後、水を加え、トルエンにて抽出し
水洗した。トルエン抽出液を芒硝にて乾燥後、減
圧下トルエンを留去し、得られた粗エーテルをシ
リカゲル250ｇのカラムクロマトグラフイー（展
開溶媒：トルエン／ｎ−ヘキサン１：１）により
精製し目的としたエーテル10.0ｇ（理論収率80
％）を得た。
n20 D 1.5710
νfilm nax 1585、1490、1425、1280、1210、1095、
1100、820、685cm-1
δccl4 1.26（Ｓ、6H）、3.30（Ｓ、2H）、4.32（Ｓ、
2H）、6.8〜7.4（ｍ、12H）
分析結果
C23H22ClFO2
計算値（％）
Ｃ 71.77 Ｈ 5.76 Cl 9.21 Ｆ 4.94
実測値（％）
Ｃ 71.95 Ｈ 5.55 Cl 9.31 Ｆ 5.02
合成実施例 ５
３−フエノキシ−４−フルオロベンジル ２−
（４−クロルフエニル）−２−メチルプロピルエ
ーテル
４−クロロネオフイルクロライド8.53ｇ、３−
フエノキシ−４−フルオロベンジルアルコール
8.72ｇ、45％NaOH3.9ｇおよびジメチルスルホ
キシド48ｇを140℃で３時間加熱撹拌した。45％
NaOH1.8ｇを追加し、さらに４時間同温度で反
応させた。反応液500mlの水中に排出し、ベンゼ
ンにて抽出し、ベンゼン抽出液を水洗したのち、
芒硝で乾燥した。減圧下にベンゼンを留去して得
られた粗エーテルをシリカゲル250ｇのカラムク
ロマトグラフイ（展開溶媒：トルエン／ｎ−ヘキ
サン１：１）により分離精製、目的としたエーテ
ル7.27ｇ（理論収率77％対消費４−クロルネオフ
イルクロライド）を得た。
n20 D 1.5710
赤外スペクトラムおよびNMRスペクトラムは
合成実施例３で得たエーテルと一致した。
合成実施例 ６
３−フエノキシ−６−クロロベンジル ２−
（４−クロロフエニル）−２−メチルプロピルエ
ーテル
２−（４−クロロフエニル）−２−メチルプロピ
ルアーコール2.0ｇ、３−フエノキシ−６−クロ
ロベンジルブロマイド3.5ｇ、50％NaOH20ｇ、
トルエチルベンジルアンモニウムブロマイド0.4
ｇを50mlセパラブルスラスコに装入し50℃で２時
間撹拌した。室温迄冷却後、氷水で冷却しながら
水、ベンゼンを加え撹拌した。分液後ベンゼン層
を水洗し芒硝で乾燥した。減圧下ベンゼンを留去
して得られた粗エーテルをシリカゲル150ｇのカ
ラムクロマトグラフイー（展開溶媒：トルエン−
ヘキサン１：１）により精製し目的としたエーテ
ル3.8ｇ（理論収率の87％）を得た。
n20 D 1.5854
νfilm nax 1500、1480、1275、1260、1215、1110、
1020、830cm-1
δccl4 1.29（Ｓ、6H）、3.44（Ｓ、2H）、4.49（Ｓ、
2H）、6.7〜7.5（ｍ、12H）
合成実施例 ７
３−フエノキシ−４−フルオロベンジル ２−
（４−クロロフエニル）−２，３−ジメチルブチ
ルエーテル
トルエン20mlに水素化ナトリウム（60％in
oil）0.60ｇを加え加熱還流し、これに２−（４−
クロロフエニル）−２−イソプロピルプロピルア
ルコール2.0ｇ／40％DMF−トルエン10ml溶液を
20分間で滴下した。このまま10分間撹拌を続けた
後、３−フエノキシ−４−フルオロベンジルブロ
マイド3.5ｇ／トルエン10ml溶液を10分間で滴下
した。更に１時間加熱還流した後、室温迄冷却し
水に排出した。トルエンで抽出し、トルエン抽出
液を水洗後、芒硝で乾燥した。減圧下、トルエン
を留去して得られた粗エーテルをシリカゲル120
ｇのカラムクロマトグラフイー（展開溶媒：トル
エン−ヘキサン１：１）により精製し目的とした
エーテル2.8ｇ（理論収率の72％）を得た。
n19.9 D 1.5656
νfilm nax 1610、1530、1510、1450、1300、1230、
1140、1120、1030cm-1
δccl4 0.62（ｄ、3H、Ｊ＝6.8Hz）、0.85（ｄ、3H、
Ｊ＝6.8Hz）、1.19（Ｓ、3H）、1.9〜2.3（ｍ、
1H）、
3.34（ｄ、1H、JAB＝8.8Hz）
3.53（ｄ、1H、JAB＝8.8Hz）
AB type
4.30（Ｓ、2H）、6.7〜7.4（ｍ、12H）
以下に出発原料一般式〔〕の製造法について
合成実施例により詳細に説明する。
合成実施例 ８
次の順序に従い合成した。
(1) アリールアセトニトリル10ｇ、KOH20ｇ、
H2O20ｇ、トリエチルベンジルアンモニウム
ブロマイド２ｇを80〜90℃に保ちながらヨウ化
メチル（アリールアセトニトリルに対し1.2モ
ル比）を１〜２時間で滴下した。次いで
KOH10ｇ、トリエチルベンジルアンモニウム
ブロマイド２ｇを追加し、同温度にて、望まし
いアルキルハライド（アリールアセトニトリル
に対し1.2モル比）を１〜４時間で滴下した。
室温迄冷却後、トルエンにて抽出した。トルエ
ン層から目的のアリールアセトニトリルのジア
ルキル体を得た。
(2) (1)で合成したアリールアセトニトリルのジア
ルキル体を50％H2SO4又は水溶性ジエチレン
グリコール−KOHで130〜150℃にて加水分解
し２−アリール−２−アルキルプロピオン酸を
得た。
代表的な化合物を以下に示す。
（Ｒ）n R1 mp
Ｈ CH3− 75〜76.5℃
３−Cl CH3− 66.5〜67.5℃
３，４−Cl2 CH3− 93.5〜94.5℃
４−CH3 CH3− 80〜81.5℃
４−Cl C2H5− 59〜61.5℃
４−OCH3 CH3− 82.5〜84℃
(3) (2)で合成した２−アリール−２−アルキル
プロピオン酸をテトラヒドロフラン中、水素化
リチウムアルミニウムで還元し目的の２−アリ
ール−２−アルキルプロピルアルコールを得
た。
合成実施例 ９
２−（４−クロロフエニル）−２−メチルプロピ
ルアルコール
以下の順序に従つて合成した。
(1) クロロベンゼン169ｇに塩化第２鉄1.5ｇを加
えた後、塩酸ガスを10分間吹込んだ。次いで、
ターシヤリー ブチルクロライド46ｇを30℃
（１時間）で滴下し、30℃で更に２時間保つた。
炭酸ナトリウム水溶液、水で洗滌後、減圧下で
蒸留し４−ターシヤリー ブチルクロロベンゼ
ン25ｇ（113℃／28mmHg）を得た。
(2) (1)で合成した４−ターシヤリーブチルクロロ
ベンゼン25ｇ、塩化スルフリル20ｇおよび触媒
量のベンゾイルパーオキサイドを加えた後昇温
し、100℃にて１時間保つた後、減圧下で蒸留
し２−（４−クロロフエニル）−２−メチル−１
−クロロ−プロパン17.0ｇ（121〜123℃／10mm
Hg）を得た。
(3) 乾燥テトラヒドロフラン100mlにマグネシウ
ム（turnings）27ｇ、触媒として少量のヨウ素
を加え、加熱還流下２−（４−クロロフエニル）
−２−メチル−１−クロロプロパン20.3ｇを30
分間で滴下し、10時間加熱還流を続けた。室温
迄冷却後、酸素ガスを１時間吹込んだ。次い
で、飽和塩化アンモニウム水溶液を加えた後、
減圧下でテトラヒドロフランの大部分を留去
し、トルエンにて抽出。トルエンを減圧下に留
去し粗アルコールを得た。
次いで、冷ヘキサンから再結晶目的の２−
（４−クロロフエニル）−２−メチルプロピルア
ルコール13.3ｇを得た。
mp 46〜48℃
分析結果
C10H13ClO
計算値（％） Ｃ 65.04 Ｈ 7.10 Cl 19.20
実測値（％） Ｃ 64.18 Ｈ 6.95 Cl 19.16
合成実施例 10
２−（３，４−メチレンジオキシフエニル）−２
−メチルプロピルアルコール
以下の順序に従い合成した。
(1)
乾燥エーテル100mlにマグネシウム
（turnings）27ｇ、触媒として少量のヨウ素を
加え、ヨウ化メチル17ｇをゆつくりと滴下し
た。滴下終了後30分間還流を続けた。次いで昇
温しながらベンゼン100mlを滴下しエーテルを
ベンゼンに置換した。
加熱還流下、原料ニトリル18.9ｇを滴下し
た。
更に３時間加熱還流した後、冷却下、6N−
HCl20mlを30分間で滴下した。次いで昇温し７
時間加熱還流した。室温迄冷却後ベンゼン層を
分離し、水洗後、芒硝で乾燥した。減圧下でベ
ンゼンを留去し目的とした２−（３，４−メチ
レンジオキシフエニル）−２−メチル−３−ブ
タノン19.2ｇを得た。
(2) 水酸化ナトリウム7.4ｇ、水35mlおよびジオ
キサン10mlに20℃以下で臭素12.8ｇを滴下し
た。
次いで昇温し、90℃で２−（３，４−メチレ
ンジオキシフエニル）−２−メチル−３−ブタ
ノン10ｇをゆつくりと滴下し、90〜95℃で２時
間加熱撹拌した。
室温迄冷却後、所定量の亜硫酸水素ナトリウ
ムを加え、トルエンにて抽出した。水層を濃塩
酸にて酸性としトルエンにて抽出した。このト
ルエン層を水洗後、芒硝にて乾燥し減圧下にト
ルエンを留去して目的とした２−（３，４−メ
チレンジオキシフエニル）−２−メチル−プロ
ピオン酸7.5ｇを得た。
(3) 上記(2)で合成した２−（３，４−メチレンジ
オキシフエニル）−２−メチル−プロピオン酸
をテトラヒドロフラン中水素リチウムアルミニ
ウムで還元し目的とした２−（３，４−メチレ
ンジオキシフエニル）−２−メチルプロピルア
ルコールを得た。
νfilm nax 3390、1495、1235、1040cm-1
δccl4 1.25（Ｓ、6H）、3.39（Ｓ、2H）、5.87（Ｓ
、
2H）、6.6〜6.9（ｍ、3H）
合成実施例 11
２−（４−ジフルオロメトキシフエニル）−２−
メチルプロピルアルコール
以下の順序に従つて合成した。
(1) ２，４−ビス（４−ヒドロキシフエニル）−
４−メチル−２−ペンテン18.0ｇを100mlアセ
トニトリルに溶解した後、50％NaOH10ｇを
滴下した。次いで60〜70℃の温度でジフルオロ
クロルメタン（Freon−22）の吹込みを開始し
た。反応必要量の約60％を吹込んだ所（約20分
後）で50％KOH10ｇを追加装入し、更に吹込
みを継続した。反応必要量の1.5倍のジフルオ
ロクロルメタンを吹込んだ所で吹込みを中止し
た。室温迄冷却後、水500mlの中に排出しトル
エンにて抽出した。トルエン層を水洗後、芒硝
で乾燥し、減圧下でトルエンを留去して得られ
た粗エーテルをシリカゲル200ｇのカラムクロ
マトグラフイー（展開溶媒：トルエン）により
精製し目的とした２，４−ビス（４−ジフルオ
ロメトキシフエニル）−４−メチル−２−ペン
テン19.2ｇを得た。収率77％。
n20 D 1.5285
(2) ２，４−ビス（４−ジフルオロメトキシフエ
ニル）−４−メチル−２−ペンテン8.0ｇをアセ
トン100mlに溶解し、30℃にてKMnO430ｇを
加えた。30℃にて10時間撹拌後、過剰の
KMnO4を分解するために、冷却下エチルアル
コール20mlを滴下した。そのまま１時間撹拌を
続けた後、生成した二酸化マンガンを過し、
水、アセトンで十分洗浄した。減圧下でアセト
ンを留去し、希塩酸水溶液を加えた後トルエン
にて抽出した。トルエン層に希NaOH水溶液
を加え、良く振りまぜた後に分液した。得られ
た水溶液層を濃塩酸にて再性とし、トルエンに
て抽出、水洗、乾燥した。
減圧下でトルエンを留去すると目的とした２
−（４−ジフルオロメトキシフエニル）−２−メ
チルプロピオン酸4.2ｇを得た。
（mp.68.5〜69.5℃）。収率84％。
δccl4 1.58（Ｓ、6H）、6.42（ｔ、1H、Ｊ＝75Hz）
（7.03（ｄ、2H、JAB＝8.8Hz）
7.37（ｄ、2H、JAB＝8.8Hz）
AB type
11.76（broad Ｓ、1H）ppn
(3) テトラヒドロフラン20ml、水素化リチウムア
ルミニウム0.5ｇの混合物に２−（４−ジフルオ
ロメトキシフエニル）−２−メチルプロピオン
酸2.0ｇ／テトラヒドロフラン10ml溶液を40℃
にて滴下した。滴下終了後、昇温し30分間リフ
ラツクスした。
室温迄冷却後、過剰の水素化リチウムアルミ
ニウムをエタノール滴下により分解し、更に水
を加え完全に分解した。生成した沈澱物を過
によつて除去し、テトラヒドロフランを減圧下
留去した。ベンゼンで抽出し、ベンゼン層を水
洗後、無水硫酸ナトリウムで乾燥した。
減圧下ベンゼンを留去し、目的の２−（４−
ジフルオロメトキシフエニル）−２−メチルプ
ロピルアルコール1.8ｇを得た。収率96％。
νfilm nax 3360、1510、1380、1220、1185、1130、
1040、835cm-1
合成実施例 12
２−（４−フルオロフエニル）−２−メチルブチ
ルアルコール
以下の順序に従つて合成した。
(1) ４−フルオロトルエン16.6ｇ、NBS30.0ｇ、
ベンゾイルパーオキサイド0.5ｇ、四塩化炭素
150mlを300mlフラスコに装入し2.0時間還流し
た。室温迄冷却後生成した沈澱物を過により
除いた後、CCl4溶液を希アルカリ、水の順に
洗浄し、芒硝で乾燥した。減圧下四塩化炭素を
留去し、粗４−フルオロベンジルブロマイド
28.8ｇを得た。
NaCN8.8ｇ、水9.0ｇの中に上記で得た粗ブ
ロマイド28.8ｇ／エタノール30ml溶液を70〜80
℃で滴下した（30分間）。次いで80℃にて5.0時
間保つた後、室温迄冷却し水に排出した。これ
にセライト、ベンゼンを加え撹拌後セライトを
過により除去した。分液後ベンゼン層を水洗
し、無水硫酸ナトリウムで乾燥した。減圧下、
ベンゼンを留去し粗４−フルオロベンジルシア
ナイド13.2ｇを得た。
νfilm nax 2270、1615、1520、1430、1240、1170、
825cm-1
(2) (1)で得た粗４−フルオロベンジルシアナイド
12.8ｇ、50％NaOH40ｇ、トリエチルベンジル
アンモニウムブロマイド２ｇをフラスコに入れ
撹拌しながらヨウ化メチル14ｇを滴下した（70
℃、15分）。
更に70℃で30分保つた後、室温迄冷却し氷水
に排出した。ベンゼンで抽出し、ベンゼン層を
水洗後、芒硝で乾燥した。減圧下、ベンゼンを
留去し、α−メチル−４−フルオロベンジルシ
アナイド13.4ｇを得た。
α−メチル−４−フルオロベンジルシアナイ
ド7.0ｇ、KOH15ｇ、H2O10ｇ、トリエチルベ
ンジルアンモニウムブロマイド2.0ｇをフラス
コに装入し、撹拌しながら80℃、１時間でエチ
ルブロマイド10mlを滴下した。次いで、同温度
に２時間保つた。以後の操作は前記の通りであ
る。粗α−エチル−α−メチル−４−フルオロ
ベンジルシアナイド7.9ｇを得た。
粗α−エチル−α−メチル−４−フルオロベ
ンジルシアナイド7.6ｇ、H2O20ml、濃硫酸20
mlをフラスコに装入し、134〜137℃で5.5時間
加熱還流した。室温迄冷却し、ベンゼンで抽出
した。ベンゼンを希アルカリで抽出し、得られ
た希アルカリ層を濃塩酸でPH7.5とし、ベンゼ
ンで抽出し、不純物を除去した。次いで、水層
を濃塩酸でPH4.6としベンゼンで抽出した。ベ
ンゼン層を水洗し、芒硝で乾燥した。減圧下ベ
ンゼンを留去し、目的の２−（４−フルオロフ
エニル）−２−メチル酪酸3.8ｇを得た。
δCDCl3 0.85（ｔ、3H、Ｊ＝７Hz）、1.55（Ｓ、
3H）、1.8〜2.3（ｍ、２）、7.0〜7.6（ｍ、4H）、
11.3（brod Ｓ、1H）
(3) テトラヒドロフラン20ml、水素化リチウムア
ルミニウム0.5ｇの混合物に２−（４−フルオロ
フエニル）−２−メチル酪酸3.0ｇ／テトラヒド
ロフラン10ml溶液を40℃で滴下した。滴下終了
後、昇温し30分間リフラツクスした。室温迄冷
却後、過剰の水素化リチウムアルミニウムをエ
タノール滴下により分解し、更に水を加え完全
に分解した。生成した沈澱物を過により除去
し、テトラヒドロフランを減圧下留去した。ベ
ンゼンで抽出し、ベンゼン層を水洗後、芒硝で
乾燥した。減圧下ベンゼンを留去し、目的の２
−（４−フルオロフエニル）−２−メチルブチル
アルコール2.6ｇを得た。
n23 D 1.5035
νfilm nax 3360、1610、1520、1240、1175、1040、
840cm-1
本合成実施例に示した目的化合物以外の前記第
１表の化合物も以上の合成実施例に準じて合成で
きる。
本発明の殺虫・殺ダニ組成物の第一の特長は、
前記第１表に示した化合物を単独で施用する場合
に比べ、広い殺虫スペクトルと相乗的に増強され
た殺虫効力を有することである。すなわち、本発
明組成物は、水銀、畑作物、棉、果樹、森林など
に被害を及ぼす農園芸森林害虫、（例えば、ツマ
グロヨコバイ、ウンカ類、メイチユウ類、ドロオ
イムシ、イネミズゾウムシ、イネゾウムシ、カメ
ムシ類、アブラムシ類、アオムシ、ヨトウ類、コ
ナガ、ネキリムシ、タネバエ、シンクイムシ、カ
イガラムシ類、ハマキガ類、ハダニ類、アメリカ
シロヒトリ、マイマイガ、キクイムシ、線虫類、
スリツプス類など）のみならず、コクゾウムシ、
ノシメコクガなどの貯蔵害虫、ハエ、カ、ゴキブ
リなどの衛生害虫など、広い範囲の害虫に対し
て、低い濃度で防除効力を有していることであ
る。
本発明組成物の第２の特長は、有機リン系殺
虫・殺ダニ剤および／またはカーバメート系殺
虫・殺ダニ剤に対しすでに抵抗性を発達させてい
る害虫に対しても顕著な殺虫・殺ダニ効果を有し
ており、しかも各種の害虫に対して薬剤抵抗性を
つけにくい性格を有していることである。
また第３の特長としては本発明組成物は一般の
有機リン系殺虫・殺ダニ剤およびカーバメート系
殺虫・殺ダニ剤にはみられない速効性を有してお
り、薬剤散布後短時間に、害虫を落下仰転させる
ことができることである。
更に第４の特長は魚類や温血動物に対して低毒
性であり、環境汚染を引きおこすおそれのないな
どの特長を有し、極めて理想に近い殺虫・殺ダニ
剤と言えることである。
本発明組成物を実際に施用する場合に、組成物
そのものを希釈して用いても十分有効であるが、
防除薬剤として使いやすくするために、各種担体
を配合して製剤とし、このものを必要に応じ希釈
するなどして施用するのが一般的である。本発明
組成物の製剤化にあたつては、何らかの特別の条
件を必要とせず、一般農薬、防疫薬に準じ、当業
界技術の熟知する方法によつて、乳剤、水和剤、
粉剤、微粒剤、粒剤、油剤、エアロゾール、加熱
燻蒸剤（蚊取線香、電気蚊取等）、フオツギング
等の煙霧剤、非加熱燻蒸剤、毒餌等の任意の剤型
に調製でき、それぞれの目的に応じ各種用途に供
しうる。
なお、本発明組成物は、光、熱、酸化等に安定
性が高いが、必要に応じ、酸化防止剤または、紫
外線吸収剤、例えば、BHT、BHA等のようなフ
エノール誘導体、ビスフエノール誘導体、フエニ
ルα−ナフチルアミン、フエニルβ−ナフチルア
ミン、フエネチジンとアセトンの縮合物等のアリ
ールアミン類またはベンゾフエノン系化合物類を
安定剤として適量加えることによつて、効果の安
定した組成物を得ることもできる。
また、多目的農薬を得ることを目的とし、本発
明組成物に誘引剤、忌避剤、殺菌剤、除草剤、植
物成長調節剤、肥料などを添加して使用すること
もできる。
本発明組成物における一般式〔〕の化合物と
協力剤との組成比は99：１〜１：99好ましくは
１：20〜１：１である。
本発明組成物を製剤した場合の有効成分濃度
は、乳剤では１〜20％、エアゾールでは0.1〜１
％、蚊取線香では0.1〜５％、電熱板上加熱せん
い燻蒸組成物では0.1〜５％（いずれも重量％）
が望ましい。
次に本発明組成物を農薬、防疫薬として用いる
場合の製剤例を若干示すが、本発明は、これらの
みに限定されるものではない。「部」はすべて
「重量部」を示す。
製剤例 １
前記第１表の化合物（「化合物番号１ないし94
のいずれか１種」以下同じ）３部、協力剤９部、
乳化剤ソルポールSM−200（東邦化学商品名）10
部、キシロール78部を撹拌混合して乳剤とする。
製剤例 ２
第１表の化合物１部、協力剤５部をアセトン20
部に溶解し粉剤用クレー94部を加えたのち撹拌
し、アセトンを蒸発せしめ粉剤とする。
製剤例 ３
第１表の化合物0.1部、協力剤0.5部を加えて白
灯油に溶解し、全体を100部として油剤とする。
製剤例 ４
第１表の化合物0.1部、協力剤0.3部キシロール
７部、脱臭灯油7.6部を混合溶解する。これをエ
アゾール容器に充てんし、バルブを取付ける。該
バルブの部分を通じて噴射剤（液化石油ガス）80
部を加圧充てんしてエアゾールとする。
製剤例 ５
第１表の化合物0.3ｇに協力剤0.9ｇ、BHT0.3
ｇを加えメタノール20mlに溶解し、蚊取線香用担
体（タブ粉、粕粉、木粉を３：５：１の割合の混
合物）99.4と均一に撹拌混合し、メタノールを蒸
散させた後、水150mlを加え充分練り合わせ成型
乾燥して蚊取線香とする。
製剤例 ６
第１表の化合物0.2ｇ、協力剤剤1.0ｇに
BHT0.2ｇを加え、クロロホルムに溶解し、厚さ
0.3cmの紙に均一に吸着させ、電熱板上加熱繊
維燻蒸組成物とする。
製剤例 ７
第１表の化合物５部に協力剤10部を加え、乳化
ソルポール355TLL（東邦化学商品名）５部を添
加し、よく撹拌し、300メツシユのケイソウ土80
部を加えてライカイ機中で充分撹拌混合して水和
剤とする。
製剤例 ８
第１表の化合物１部に協力剤５部を加え、クレ
ーを90部、トヨリグニンCT（東洋紡登録商品名）
４部を加え、よく混合し、さらに水を加えて撹拌
混合後造粒機にて製粒し、乾燥して粒剤とする。
製剤例 ９
第１表の化合物0.1部、協力剤0.3部、脱臭灯油
11.6部、乳化剤アトモス300（アトラスケミカル社
登録商品名）１部とを混合し、純水50部を加え乳
化させる。これに脱臭ブタン、脱臭プロパンの
３：１混合物の37部とともにエアゾール容器に充
てんし、ウオーターベースエアゾールとする。
次に本発明の殺虫・殺ダニ剤の適用できる具体
的な害虫名をあげる〔学名−（和名）〕。
１ Hemiptera（半翅目）
Nephotettix cincticeps Uhler（ツマグロヨ
コバイ）
Sogatella furcifera Horvath（セジロウン
カ）
Nilaparvata lugens Sta゜l（トビイロウンカ）
Laodelphax striatellus Fallen（ヒメトビウ
ンカ）
Eurydema rugosum Motschulsky（ナガメ）
Eysarcoris parvus Uhler（トゲシラホシカ
メムシ）
Halyomorpha mista Uhler（クサギカメム
シ）
Lagynotomus elongatus Dallas（イネカメ
ムシ）
Nezara viridula Linne′（ミナミアオカメム
シ）
Cletus trigonus Thunberg′（ヒメハリカメ
ムシ）
Stephanitis nashi Esaki et Takeya（ナシ
グンバイ）
Stephanitis pyrioides Scott（ツツジグンバ
イ）
Psyllapyrisuga Fo¨rster（ナシキジラミ）
Psyllamali Schmidberg′er（リンゴキジラ
ミ）
Aleurolobus taonabae Kuwana（ブドウコ
ナジラミ）
Dialeurodes citri Ashmead（ミカンノコナ
ジラミ）
Trialeurodes vaporaiorum Westwood（オ
ンシツコナジラミ）
Aphis gossypii Glover（ワタアブラムシ）
Brevicoryne brassicae Linne′（ダイコンア
ブラムシ）
Myzus persicae Sulzer（モモアカアブラム
シ）
Rhopalosiphum maidis Fitch（キビクビレ
アブラムシ）
Icerya purchasi Maskell（イセリヤカイガ
ラムシ）
Planococcus citri Risso（ミカンコナカイガ
ラムシ）
Unaspis yanonensis Kuwana（ヤノネカイ
ガラムシ）
２ Lepidoptera（鱗翅目）
Canephora asiatica Staudinger（ミノガ）
Spulerina astaurcta Meyrick（ナシホソガ）
Phyllomorycter ringoneella Matsumura
（キンモンホソガ）
Plutella xylostella Linn′e（コナガ）
Promalactis inopisema Butler（ワタミガ）
Adoxophyes orana Fischer von
Ro¨slerstamm（コカクモンハマキ）
Bactra furfuran′a Haworth（イグサシンム
シガ）
Leguminivora glycinivorella Matsumura
（マメシンクイガ）
Cnaphalocrocis medinalis Guene′e（コブノ
メイガ）
Etiella zinckenella Treitschke（シロイチモ
ジマダラメイガ）
Ostrinia furnacalis Guene′e（アワノメイ
ガ）
Pleurophya derogata Fabricus（ワタノメイ
ガ）
Hyphantria cunea Drury（アメリカシロヒ
トリ）
Abraxas miranda Butler（ユウマダラエダ
シヤク）
Lymantria dispar japonica Motschulsky
（マイマイガ）
Phalera fiavescens Bremer et Grey（モン
クロシヤチホコ）
Agrotis segetum Denis et Schiffer
mu¨ller（カブラヤガ）
Helicoverpa armigera Hu¨bner（オオタバコ
ガ）
Pseudaletia separata Walker（アワヨトウ）
Mamestra brassicae Linne′（ヨトウガ）
Plusia nigrisigna Walker（タマナギンウワ
バ）
Spodoptera litura Fablicirs（ハスモンヨト
ウ）
Parnara guttata Bremer et Grey（イネツ
トムシ）
Pieris rapae crucivora Boisduval（モンシ
ロチヨウ）
Chilo suppressalis Walker（ニカメイガ）
３ Coleoptera（鞘翅目）
Melanotus fortnumi Cande′ze（マルクビク
シコメツキ）
Anthrenus verbasci Lunne′（ヒメマルカツ
オブシムシ）
Tenebroides mauritanicus Linne′（コクヌ
スト）
Lyctus brunneus Stephens（ヒラタキクイム
シ）
Henosepilachna vigintioctopunctata
Fablicius（ニジユウヤホシテントウ）
Monochamus alternatus Hope（マツノマダ
ラカミキリ）
Xylotrechus pyrrhoderus Bates（ブドウト
ラカミキリ）
Aulacophora femoralis Motschlusky（ウリ
ハムシ）
Oulema oryzae Kuwayama（イネドロオイ
ムシ）
Phyllotreta striolata Fablicius（キスジノミ
ハムシ）
Callosobruchus chinensis Linne′（アズキゾ
ウムシ）
Echinocnemis squameus Billberg（イネゾ
ウムシ）
Sitophilus oryzae Linne′（ココクゾウ）
Apoderus erythrogaster Vollenhoven（ヒ
メクロオトシブミ）
Rhynchites heros Roelofs（モモチヨツキリ
ゾウムシ）
Anomala cuprea Hope（ドウガネブイブイ）
Popillia japonica Newman（マメコガネ）
４ Hymenoptera（膜翅目）
Athalia rosae japonensis Rohwer（カブラ
ハバチ）
Arge similis Vollenhoven（ルリチユウレン
ジ）
Arge pagana Panzer（チユウレンジバチ）
５ Piptera（双翅目）
Tipula aino Alexander（キリウジガガン
ボ）
Culex pipiens fatigans Wiedemann（ネツ
タイイエカ）
Aedes aegypti Linne′（ネツタイシマカ）
Asphondylia sp.（ダイズサヤタマバエ）
Hylemya antiqua Meigen（タマネギバエ）
Hylemya platura Meigen（タネバエ）
Musca domestica vicina Macquart（イエ
バエ）
Dacus cucurbitae Coquillett（ウリミバエ）
Chlorops oryzae Matsumura（イネカラバ
エ）
Agromyza oryzae Munakata（イネハモグ
リバエ）
６ Siphonaptera（穏翅目）
Pulex irritans Linne′（ヒトノミ）
Xenopsylla cheopis Rothschild（ケオプス
ネズミノミ）
Ctenocephalides Canis Curtis（イヌノミ）
７ Thysanoptera（総翅目）
Scirtothrips dorsalis Hood（チヤノキイロ
アザミウマ）
Thrips tabaci Lindeman（ネギアザミウマ）
Chloethrips oryzae Williams（イネアザミ
ウマ）
８ Anoplura（シラミ目）
Pediculus humanus corporis De Geer（コ
ロモジラミ）
Phthirus pubus Linn′e（ケジラミ）
Haematopinus eurystrnus Nitzsh（ウシジ
ラミ）
９ Psocoptera（チヤタテムシ目）
Trogium pulsatsrium Lunne′（コナチヤタ
テムシ）
Liposcelis bostrychophilus Badonnel（ヒラ
タチヤタテ）
10 Orthoptera（直翅目）
Gryllotalpa africana palisot de Beauvois
（ケラ）
Locusta migratoria danica Linne′（トノサ
マバツタ）
Oxya yezoensis Shiraki（コバネイナゴ）
11 Dictyoptera（網翅目）
Blattella germanica Linne′（チヤバネゴキ
ブリ）
Periplaneta fuliginosa Serville（クロゴキ
ブリ）
12 Acarina（ダニ目）
Boophilus microplus Canestrini（オウシマ
ダニ）
Polyphagoharsonemus latus Banks（チヤ
ノホコリダニ）
Panonychus cutri McGregor（ミカンハダ
ニ）
Tetranychus ciunnabarimus Boisduval（ニ
セナミハダニ）
Tetranychus urticae Koch（ナミハダニ）
Rhizoglyphis echinophus Fumouze et
Robin（ネダニ）
次に、本発明組成物の殺虫・殺ダニ剤としての
すぐれた作用効果について、試験例をあげて詳細
に説明する。
試験例 １
チヤバネゴキブリに対する効果
直径９cm、高さ５cmの腰高シヤーレ底面に第１
表に示した化合物のアセトン所定濃度液を滴下し
風乾してドライフイルムを作つた。一方、同様の
方法で第１表に示した化合物と協力剤Ｓ−421を
１：３の比率で混合したアセトン所定濃度液を滴
下し風乾して化合物のドライフイルムを作つた。
腰高シヤーレの内壁にバターを塗り、チヤコバネ
ゴキブリの雌成虫をシヤーレ当り10頭放ち、24時
間後の死虫率を求め各化合物単独の場合及び化合
物と協力剤混合の場合のLD−50値を求めた。い
ずれの化合物の場合も単独処理の場合よりＳ−
421を混合した場合の方が効力が高く、２倍以上
の活性の上昇が認められた。
試験例 ２
ハスモンヨトウに対する効果
直径10cmのポリエチレンカツプにハスモンヨト
ウの３令幼虫を入れ、第１表に示した化合物単独
及び化合物と協力剤を１：２に混合した場合の乳
剤を製剤例１に準じてつくり、水で希釈して所定
濃度とし、散布塔を用いて各カツプ当り２mlあて
直接幼虫に散布した。直ちに人工飼料をあたえ、
24時間後、各々の死虫率を求めLC−50値を算出
した。
各化合物単独の場合にくらべ協力剤を混合した
場合はいずれの組合せにおいても２倍以上の効力
増加が認められた。
試験例 ３
ハダニに対する効果
直径15mmのインゲンリーフデイスク上にナミハ
ダニ幼虫を放ち、試験例２と同様の乳剤を散布
し、各々のLC−50値を求め効果を比較したとこ
ろ、第１表に示した化合物単独でのLC−50値と
協力剤を加えた場合のLC−50値は後者が1/2以下
の値を示し高い相乗効果を認めた。
試験例 ４
キヤンベルのターンテーブル法（ソープアンド
サニタリイケミカルスVol4No.６ 119頁（1938）〕
によりイエバエ成虫（雌）20頭を使用し、製剤例
３に準じてつくつた第１表に示した化合物単独の
油剤と、該化合物と協力剤とを１：３の割合で混
合した油剤の各１mlをスプレーし、供試したイエ
バエの半数が落下横転する時間（以下「KT−50
値」と略す）を求め比較した。いずれの化合物の
場合も協力剤を添加した油剤のKT−50値は化合
物単独の場合の1/2以下の値を示し、殺虫速度を
早めることができた。
試験例 ５
第１表に示した化合物単独および協力剤Ｓ−
421との混合物の蚊取線香を製剤例５に準じて作
つた。直径20cm、高さ43cmのガラス円筒内にアカ
イエカ雌成虫を20頭放ち、順化させた後各蚊取線
香に点火、２分間円筒内で燻煙し、アカイエカ成
虫の落下横転時間を調査するとともに、横転虫を
あらかじめ用意した腰高シヤーレに５％砂糖水を
ワタに含ませたものとともに入れ24時間後死虫数
を調査した。
結果を下記の第２表に示す。この表のKT−50
値から明らかなようにいずれの化合物も各単独の
場合よりＳ−421と混合したものは殺虫速度が早
くなつた。[Table] The compound represented by the above general formula () is a new compound, and examples of its synthesis are shown below. The compound represented by the general formula [] is the compound represented by the general formula [] The compound represented by the general formula [] [In these formulas, Ar, R 1 , R 2 , R 3 , and R 4 each represent the above-mentioned meanings, and one of the groups A and B represents a halogen atom, and the other group represents an X-
Reacting with a compound represented by the group M (in this formula, X represents the above meaning and M represents a hydrogen atom, an alkali metal atom or an alkaline earth metal atom), or both represent a hydroxyl group] obtained by. Next, typical examples of the compounds of the present invention obtained in this manner are shown, but of course the compounds of the present invention are not limited to these examples. In addition, the compound of the present invention has an asymmetric carbon when R 1 and R 2 are different groups in the general formula [], and optical isomers exist, but mixtures of these optical isomers and these components It includes. 3-(4-fluorophenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-phenyl-2-methylpropyl ether and thioether , 3-phenoxy-4-chlorobenzyl 2-
(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-
Fluorobenzyl 2-(4-methoxyphenyl)
-2-Methylpropyl ether and thioether, 3-(4-fluorophenoxy)-4-fluorobenzyl 2-(4-methoxyphenyl)-2-
Methyl propyl ether and thioether, 3
-Phenoxy-4-fluorobenzyl 2-(4
-chlorophenyl)-2-ethylbutyl ether and thioether, 3-phenoxy-6-chlorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-
(4-fluorophenoxy)-4-fluorobenzyl 2-(3,4-dichlorophenyl)-2-methylbutyl ether and thioether 3-phenoxy-4-fluorobenzyl 2-
(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-(2-fluorophenoxy)-4-fluorobenzyl 2-(3,4
-dichlorophenyl)-2-methylpropyl ether and thioether, 3-(2-fluorophenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4 -fluorobenzyl 2-(2-naphthalen-2-yl)-
2-Methylpropyl ether and thioether, 3-(4-methoxyphenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-
Phenoxy-4-fluorobenzyl 2-(3,
4-dichlorophenyl)-2-methylpropyl ether and thioether, 3-(4-bromophenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluoro Benzyl 2-(4-bromophenyl)-2-methylpropyl ether and thioether, 3-
Phenoxy-4-fluorobenzyl 2-(3-
Ethoxy-4-bromophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylbutyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(4 -difluoromethoxyphenyl)-
2-Methylpropyl ether and thioether, 3-(3-methylphenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-
(2-fluorophenoxy)-4-fluorobenzyl 2-(4-methylthiophenyl)-2-methylpropyl ether and thioether, 3-(3
-fluorophenoxy)-5-fluorobenzyl 2-(3-chloro-4-methoxyphenyl)-2
- methylpropyl ether and thioether,
3-phenoxy-6-bromobenzyl 2-(4
-methylphenyl)-2-methylpropyl ether and thioether, 3-(4-fluorophenoxy)-4-fluorobenzyl 2-(3,4-
dichlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-2-fluorobenzyl 2-phenyl-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(4-chlorophenyl)-2 , 3-dimethylbutyl ether and thioether, 3-phenoxy-6-bromobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-(4-
Fluorophenoxy)-2-fluorobenzyl
2-phenyl-2-methylpropyl ether and thioether, 3-(4-fluorophenoxy)
-5-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(4-fluorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy -5-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(4-nitrophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-5 -chlorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(3,4-methylenedioxyphenyl)
-2-methylpropyl ether and thioether, 3-phenoxybenzyl 2-(4-bromophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dibromophenyl)-2-methyl Propyl ether, 3-phenoxybenzyl 2-(4-chlorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2 -(3-bromo-4
-chlorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dichlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-bromophenyl)-2- Methylpropyl ether, 3-phenoxybenzyl 2-(4-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4
-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dichlorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4
-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-dibromophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-chlorophenyl)-2- Methylpropyl ether, 3-phenoxybenzyl 2-(4-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4
-fluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-difluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-difluorophenyl)-2- Ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4
-fluorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4
-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-fluoro-4
-bromophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-fluoro-4
-bromophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-bromo-3
-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-bromo-3
-chloro-phenyl)-2-ethylpropyl ether, etc. Next, the above general formula of the present invention []
The method for producing the compound represented by will be explained in more detail by giving synthesis examples. Synthesis Example 1 3-(4-bromophenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether 0.9 g of sodium hydride (60% in oil) was added to 20 ml of dry acetonitrile, and then 2- (4-chlorophenyl)-2-methylpropyl alcohol 2.8
g/10ml acetonitrile solution was added dropwise at 50°C. After heating under reflux for 30 minutes, 3-(4-bromophenoxy)-4-fluorobenzylbromide 6.6
g/10ml acetonitrile solution was added dropwise over 10 minutes,
Further, the mixture was heated under reflux for 1 hour. After cooling to room temperature,
It was drained into water and extracted with toluene. The toluene extract was washed with saturated saline and dried with Glauber's salt. The crude ether obtained by distilling toluene off under reduced pressure was subjected to column chromatography on 150 g of silica gel (developing solvent: toluene/n-hexane 1:
1) to obtain 4.6 g (theoretical yield: 65%) of the desired ether. n 20 D 1.5806 ν film nax 1590, 1490, 1435, 1295, 1225, 1105,
1020, 830cm -1 δ ccl4 1.29 (S, 6H), 3.32 (S, 2H), 4.32 (S,
2H), 6.7-7.5 (m, 11H) Analysis result C 23 H 21 BrClFO 2 Calculated value (%) C 59.56 H 4.56
Br 17.23 Cl 7.65 F 4.10 Actual value (%) C 59.85 H 4.64
Br 17.01 Cl 7.77 F 4.00 Synthesis Example 2 3-Phenoxy-4-fluorobenzyl 2-
(4-Methylphenyl)-methylpropyl ether Sodium hydride (60% in
0.63 g of oil) was heated to reflux, and 1.7 g of 2-(4-methylphenyl)-2-methylpropyl alcohol was added to this.
g/25% DMF-toluene solution (10 ml) was added dropwise over 15 minutes. After continuing stirring for 10 minutes, 3-
Phenoxy-4-fluorobenzyl chloride
A solution of 3.0 g/10 ml of toluene was added dropwise over 20 minutes.
After further heating under reflux for 1.5 hours, the mixture was cooled to room temperature and drained into water. After washing the extract with toluene and water, it was dried with Glauber's salt. The crude ether obtained by distilling toluene off under reduced pressure was purified by column chromatography on a 100 g silica gel column (developing solvent: toluene/n-hexane 1:1) to obtain the desired purified ether.
2.7 g (71% theoretical yield) was obtained. n 20 D 1.5611 ν film nax 1600, 1500, 1435, 1290, 1225, 1105,
825, 695cm -1 δ ccl4 1.30 (S, 6H), 2.27 (S, 3H), 3.34 (S,
2H), 4.34 (S, 2H), 6.8-7.4 (m, 12H) Analysis result C 24 H 25 FO 2 Calculated value (%) C 79.09 H 6.91 F 5.21 Actual value (%) C 79.23 H 7.01 F 5.42 Synthesis implementation Example 3 3-phenoxy-4-fluorobenzyl 2-
(4-chlorophenyl)-2-methylpropyl ether 50% NaOH aqueous solution 20g, 2-(4-chlorophenyl)-2-methylpropyl alcohol 6.0g, 3
-Phenoxy-4-fluorobenzyl bromide
8.6 g and 1.1 g of tetrabutylammonium bromide were added, and the mixture was heated and stirred at 80° C. for 1 hour.
After cooling to room temperature, water was added, extracted with toluene, and washed with water. After drying the toluene extract over Glauber's salt, the toluene was distilled off under reduced pressure, and the resulting crude ether was purified by column chromatography on 250 g of silica gel (developing solvent: toluene/n-hexane 1:1) to obtain the desired product. Ether 10.0g (theoretical yield 80
%) was obtained. n 20 D 1.5710 ν film nax 1585, 1490, 1425, 1280, 1210, 1095,
1100, 820, 685cm -1 δ ccl4 1.26 (S, 6H), 3.30 (S, 2H), 4.32 (S,
2H), 6.8-7.4 (m, 12H) Analysis result C 23 H 22 ClFO 2 Calculated value (%)
C 71.77 H 5.76 Cl 9.21 F 4.94 Actual value (%)
C 71.95 H 5.55 Cl 9.31 F 5.02 Synthesis Example 5 3-Phenoxy-4-fluorobenzyl 2-
(4-Chlorphenyl)-2-methylpropyl ether 4-chloroneofyl chloride 8.53g, 3-
Phenoxy-4-fluorobenzyl alcohol
8.72g, 45% NaOH3.9g and 48g dimethyl sulfoxide were heated and stirred at 140°C for 3 hours. 45%
1.8 g of NaOH was added and the reaction was continued at the same temperature for an additional 4 hours. The reaction solution was drained into 500ml of water, extracted with benzene, and the benzene extract was washed with water.
Dried with Glauber's salt. The crude ether obtained by distilling off benzene under reduced pressure was separated and purified by column chromatography using 250 g of silica gel (developing solvent: toluene/n-hexane 1:1) to obtain 7.27 g of the desired ether (theoretical yield: 77 % consumed 4-chlorneofyl chloride). n 20 D 1.5710 The infrared spectrum and NMR spectrum were consistent with the ether obtained in Synthesis Example 3. Synthesis Example 6 3-phenoxy-6-chlorobenzyl 2-
(4-chlorophenyl)-2-methylpropyl ether 2-(4-chlorophenyl)-2-methylpropyl alcohol 2.0 g, 3-phenoxy-6-chlorobenzyl bromide 3.5 g, 50% NaOH 20 g,
Toluethylbenzylammonium bromide 0.4
g was placed in a 50 ml separable flask and stirred at 50°C for 2 hours. After cooling to room temperature, water and benzene were added and stirred while cooling with ice water. After separation, the benzene layer was washed with water and dried with sodium sulfate. The crude ether obtained by distilling off benzene under reduced pressure was subjected to column chromatography on 150 g of silica gel (developing solvent: toluene-
3.8 g (87% of theoretical yield) of the desired ether was obtained by purification using hexane (1:1). n 20 D 1.5854 ν film nax 1500, 1480, 1275, 1260, 1215, 1110,
1020, 830cm -1 δ ccl4 1.29 (S, 6H), 3.44 (S, 2H), 4.49 (S,
2H), 6.7-7.5 (m, 12H) Synthesis Example 7 3-Phenoxy-4-fluorobenzyl 2-
(4-chlorophenyl)-2,3-dimethylbutyl ether Sodium hydride (60% in
Add 0.60g of 2-(4-
chlorophenyl)-2-isopropylpropyl alcohol 2.0g/40% DMF-toluene 10ml solution
It was added dropwise over 20 minutes. After continuing to stir for 10 minutes, a solution of 3.5 g of 3-phenoxy-4-fluorobenzyl bromide/10 ml of toluene was added dropwise over 10 minutes. After further heating under reflux for 1 hour, the mixture was cooled to room temperature and drained into water. It was extracted with toluene, and the toluene extract was washed with water and then dried with Glauber's salt. The crude ether obtained by distilling toluene off under reduced pressure was purified by silica gel 120.
The product was purified by column chromatography (developing solvent: toluene-hexane 1:1) to obtain 2.8 g of the desired ether (72% of theoretical yield). n 19.9 D 1.5656 ν film nax 1610, 1530, 1510, 1450, 1300, 1230,
1140, 1120, 1030cm -1 δ ccl4 0.62 (d, 3H, J=6.8Hz), 0.85 (d, 3H,
J = 6.8Hz), 1.19 (S, 3H), 1.9~2.3 (m,
1H), 3.34 (d, 1H, J AB = 8.8Hz) 3.53 (d, 1H, J AB = 8.8Hz) AB type 4.30 (S, 2H), 6.7~7.4 (m, 12H) Below is the general formula of the starting materials. The method for producing [] will be explained in detail with reference to Synthesis Examples. Synthesis Example 8 It was synthesized according to the following order. (1) 10g of arylacetonitrile, 20g of KOH,
Methyl iodide (1.2 molar ratio to arylacetonitrile) was added dropwise to 20 g of H 2 O and 2 g of triethylbenzylammonium bromide over 1 to 2 hours while maintaining the temperature at 80 to 90°C. then
10 g of KOH and 2 g of triethylbenzylammonium bromide were added, and at the same temperature, a desired alkyl halide (1.2 molar ratio to arylacetonitrile) was added dropwise over 1 to 4 hours.
After cooling to room temperature, it was extracted with toluene. The desired dialkyl form of arylacetonitrile was obtained from the toluene layer. (2) The dialkyl form of arylacetonitrile synthesized in (1) was hydrolyzed with 50% H 2 SO 4 or water-soluble diethylene glycol-KOH at 130 to 150°C to obtain 2-aryl-2-alkylpropionic acid. Representative compounds are shown below. (R) n R 1 mp H CH 3 - 75 to 76.5℃ 3-Cl CH 3 - 66.5 to 67.5℃ 3,4-Cl 2 CH 3 - 93.5 to 94.5℃ 4-CH 3 CH 3 - 80 to 81.5℃ 4 -Cl C 2 H 5 - 59~61.5℃ 4-OCH 3 CH 3 - 82.5~84℃ (3) Reducing the 2-aryl-2-alkylpropionic acid synthesized in (2) with lithium aluminum hydride in tetrahydrofuran. The desired 2-aryl-2-alkylpropyl alcohol was obtained. Synthesis Example 9 2-(4-chlorophenyl)-2-methylpropyl alcohol Synthesized according to the following sequence. (1) After adding 1.5 g of ferric chloride to 169 g of chlorobenzene, hydrochloric acid gas was blown in for 10 minutes. Then,
Tertiary butyl chloride 46g at 30℃
(1 hour) and kept at 30°C for an additional 2 hours.
After washing with an aqueous sodium carbonate solution and water, the mixture was distilled under reduced pressure to obtain 25 g of 4-tert-butylchlorobenzene (113°C/28mmHg). (2) After adding 25 g of 4-tert-butylchlorobenzene synthesized in (1), 20 g of sulfuryl chloride, and a catalytic amount of benzoyl peroxide, the temperature was raised, kept at 100°C for 1 hour, and then distilled under reduced pressure. 2-(4-chlorophenyl)-2-methyl-1
-chloro-propane 17.0g (121~123℃/10mm
Hg) was obtained. (3) Add 27 g of magnesium (turnings) and a small amount of iodine as a catalyst to 100 ml of dry tetrahydrofuran, and add 2-(4-chlorophenyl) under heating under reflux.
-2-Methyl-1-chloropropane 20.3g 30
The mixture was added dropwise over a period of minutes, and heating and refluxing was continued for 10 hours. After cooling to room temperature, oxygen gas was blown in for 1 hour. Then, after adding a saturated ammonium chloride aqueous solution,
Most of the tetrahydrofuran was distilled off under reduced pressure and extracted with toluene. Toluene was distilled off under reduced pressure to obtain crude alcohol. Then, the 2-
13.3 g of (4-chlorophenyl)-2-methylpropyl alcohol was obtained. mp 46-48℃ Analysis result C 10 H 13 ClO Calculated value (%) C 65.04 H 7.10 Cl 19.20 Actual value (%) C 64.18 H 6.95 Cl 19.16 Synthesis example 10 2-(3,4-methylenedioxyphenyl )-2
-Methylpropyl alcohol Synthesized according to the following sequence. (1) To 100 ml of dry ether were added 27 g of magnesium (turnings) and a small amount of iodine as a catalyst, and 17 g of methyl iodide was slowly added dropwise. Refluxing was continued for 30 minutes after the completion of the dropwise addition. Next, 100 ml of benzene was added dropwise while increasing the temperature to replace the ether with benzene. While heating under reflux, 18.9 g of raw material nitrile was added dropwise. After further heating under reflux for 3 hours, 6N-
20 ml of HCl was added dropwise over 30 minutes. Then the temperature was raised to 7
The mixture was heated to reflux for an hour. After cooling to room temperature, the benzene layer was separated, washed with water, and dried with Glauber's salt. Benzene was distilled off under reduced pressure to obtain 19.2 g of the desired 2-(3,4-methylenedioxyphenyl)-2-methyl-3-butanone. (2) 12.8 g of bromine was added dropwise to 7.4 g of sodium hydroxide, 35 ml of water, and 10 ml of dioxane at below 20°C. Next, the temperature was raised to 90°C, and 10 g of 2-(3,4-methylenedioxyphenyl)-2-methyl-3-butanone was slowly added dropwise thereto, followed by heating and stirring at 90 to 95°C for 2 hours. After cooling to room temperature, a predetermined amount of sodium bisulfite was added and extracted with toluene. The aqueous layer was acidified with concentrated hydrochloric acid and extracted with toluene. This toluene layer was washed with water, dried over Glauber's salt, and the toluene was distilled off under reduced pressure to obtain 7.5 g of the desired 2-(3,4-methylenedioxyphenyl)-2-methyl-propionic acid. (3) The 2-(3,4-methylenedioxyphenyl)-2-methyl-propionic acid synthesized in (2) above was reduced with lithium aluminum hydrogen in tetrahydrofuran to obtain the desired 2-(3,4-methylene Dioxyphenyl)-2-methylpropyl alcohol was obtained. ν film nax 3390, 1495, 1235, 1040cm -1 δ ccl4 1.25 (S, 6H), 3.39 (S, 2H), 5.87 (S
,
2H), 6.6-6.9 (m, 3H) Synthesis Example 11 2-(4-difluoromethoxyphenyl)-2-
Methylpropyl alcohol Synthesized according to the following sequence. (1) 2,4-bis(4-hydroxyphenyl)-
After dissolving 18.0 g of 4-methyl-2-pentene in 100 ml of acetonitrile, 10 g of 50% NaOH was added dropwise. Then blowing difluorochloromethane (Freon-22) was started at a temperature of 60-70°C. When about 60% of the amount required for the reaction had been blown into the reactor (after about 20 minutes), 10 g of 50% KOH was additionally charged, and the blowing was continued. Blowing was stopped when 1.5 times the amount of difluorochloromethane required for the reaction was blown into the reactor. After cooling to room temperature, it was poured into 500 ml of water and extracted with toluene. The toluene layer was washed with water, dried with Glauber's salt, and the toluene was distilled off under reduced pressure. The resulting crude ether was purified by column chromatography using 200 g of silica gel (developing solvent: toluene) to obtain the desired 2,4-bis. 19.2 g of (4-difluoromethoxyphenyl)-4-methyl-2-pentene was obtained. Yield 77%. n 20 D 1.5285 (2) 8.0 g of 2,4-bis(4-difluoromethoxyphenyl)-4-methyl-2-pentene was dissolved in 100 ml of acetone, and 30 g of KMnO 4 was added at 30°C. After stirring for 10 hours at 30℃, excess
To decompose KMnO 4 , 20 ml of ethyl alcohol was added dropwise under cooling. After continuing to stir for 1 hour, the produced manganese dioxide was filtered,
Thoroughly washed with water and acetone. Acetone was distilled off under reduced pressure, a dilute aqueous hydrochloric acid solution was added, and the mixture was extracted with toluene. A dilute NaOH aqueous solution was added to the toluene layer, and after shaking well, the layers were separated. The resulting aqueous layer was reconstituted with concentrated hydrochloric acid, extracted with toluene, washed with water, and dried. When toluene is distilled off under reduced pressure, the target 2
4.2 g of -(4-difluoromethoxyphenyl)-2-methylpropionic acid was obtained. (mp.68.5~69.5℃). Yield 84%. δ ccl4 1.58 (S, 6H), 6.42 (t, 1H, J = 75Hz) (7.03 (d, 2H, J AB = 8.8Hz) 7.37 (d, 2H, J AB = 8.8Hz) AB type 11.76 (broad S , 1H) ppn (3) Add a solution of 2.0 g of 2-(4-difluoromethoxyphenyl)-2-methylpropionic acid/10 ml of tetrahydrofuran to a mixture of 20 ml of tetrahydrofuran and 0.5 g of lithium aluminum hydride at 40°C.
It was dripped at. After the dropping was completed, the temperature was raised and refluxed for 30 minutes. After cooling to room temperature, excess lithium aluminum hydride was decomposed by dropping ethanol, and water was further added to completely decompose it. The formed precipitate was removed by filtration, and tetrahydrofuran was distilled off under reduced pressure. Extraction was performed with benzene, and the benzene layer was washed with water and then dried over anhydrous sodium sulfate. Benzene was distilled off under reduced pressure to obtain the desired 2-(4-
1.8 g of difluoromethoxyphenyl)-2-methylpropyl alcohol was obtained. Yield 96%. ν film nax 3360, 1510, 1380, 1220, 1185, 1130,
1040, 835 cm -1 Synthesis Example 12 2-(4-fluorophenyl)-2-methylbutyl alcohol Synthesized according to the following sequence. (1) 4-fluorotoluene 16.6g, NBS30.0g,
0.5g benzoyl peroxide, carbon tetrachloride
150 ml was charged into a 300 ml flask and refluxed for 2.0 hours. After cooling to room temperature, the formed precipitate was removed by filtration, and the CCl 4 solution was washed with dilute alkali and water in that order, and dried with Glauber's salt. Carbon tetrachloride was distilled off under reduced pressure to obtain crude 4-fluorobenzyl bromide.
28.8g was obtained. A solution of 28.8 g of the crude bromide obtained above/30 ml of ethanol in 8.8 g of NaCN and 9.0 g of water was added at 70 to 80 g.
It was added dropwise (30 minutes) at °C. The mixture was then kept at 80°C for 5.0 hours, cooled to room temperature, and discharged into water. Celite and benzene were added to this and stirred, and then Celite was removed by filtration. After separation, the benzene layer was washed with water and dried over anhydrous sodium sulfate. Under reduced pressure
Benzene was distilled off to obtain 13.2 g of crude 4-fluorobenzyl cyanide. ν film nax 2270, 1615, 1520, 1430, 1240, 1170,
825cm -1 (2) Crude 4-fluorobenzyl cyanide obtained in (1)
12.8 g, 50% NaOH, 40 g, and 2 g of triethylbenzylammonium bromide were placed in a flask, and 14 g of methyl iodide was added dropwise with stirring (70 g).
°C, 15 min). After further keeping at 70°C for 30 minutes, it was cooled to room temperature and drained into ice water. Extraction was performed with benzene, and the benzene layer was washed with water and dried over Glauber's salt. Benzene was distilled off under reduced pressure to obtain 13.4 g of α-methyl-4-fluorobenzyl cyanide. A flask was charged with 7.0 g of α-methyl-4-fluorobenzyl cyanide, 15 g of KOH, 10 g of H 2 O, and 2.0 g of triethylbenzylammonium bromide, and 10 ml of ethyl bromide was added dropwise at 80° C. over 1 hour with stirring. Then, it was kept at the same temperature for 2 hours. The subsequent operations are as described above. 7.9 g of crude α-ethyl-α-methyl-4-fluorobenzyl cyanide was obtained. Crude α-ethyl-α-methyl-4-fluorobenzyl cyanide 7.6 g, H 2 O 20 ml, concentrated sulfuric acid 20
ml was placed in a flask and heated under reflux at 134-137°C for 5.5 hours. The mixture was cooled to room temperature and extracted with benzene. Benzene was extracted with dilute alkali, and the resulting dilute alkali layer was adjusted to pH 7.5 with concentrated hydrochloric acid and extracted with benzene to remove impurities. Next, the aqueous layer was adjusted to pH 4.6 with concentrated hydrochloric acid and extracted with benzene. The benzene layer was washed with water and dried with Glauber's salt. Benzene was distilled off under reduced pressure to obtain 3.8 g of the desired 2-(4-fluorophenyl)-2-methylbutyric acid. δ CDCl3 0.85 (t, 3H, J=7Hz), 1.55 (S,
3H), 1.8-2.3 (m, 2), 7.0-7.6 (m, 4H),
11.3 (brod S, 1H) (3) A solution of 3.0 g of 2-(4-fluorophenyl)-2-methylbutyric acid/10 ml of tetrahydrofuran was added dropwise to a mixture of 20 ml of tetrahydrofuran and 0.5 g of lithium aluminum hydride at 40°C. After the dropping was completed, the temperature was raised and refluxed for 30 minutes. After cooling to room temperature, excess lithium aluminum hydride was decomposed by dropping ethanol, and water was further added to completely decompose it. The formed precipitate was removed by filtration, and tetrahydrofuran was distilled off under reduced pressure. Extraction was performed with benzene, and the benzene layer was washed with water and dried over Glauber's salt. Benzene was distilled off under reduced pressure to obtain the desired 2
2.6 g of -(4-fluorophenyl)-2-methylbutyl alcohol was obtained. n 23 D 1.5035 ν film nax 3360, 1610, 1520, 1240, 1175, 1040,
840cm -1 Compounds in Table 1 above other than the target compounds shown in this synthesis example can also be synthesized according to the above synthesis examples. The first feature of the insecticidal/acaricidal composition of the present invention is that
It has a broader insecticidal spectrum and synergistically enhanced insecticidal efficacy than when the compounds shown in Table 1 are applied alone. That is, the composition of the present invention is effective against mercury, agricultural, horticultural, and forest pests that cause damage to field crops, cotton, fruit trees, forests, etc. (e.g., leafhoppers, planthoppers, beetles, rice beetles, rice weevils, rice weevils, stink bugs, and aphids). , green caterpillars, armyworms, mealybugs, mealybugs, seed flies, sink beetles, scale insects, leafhoppers, spider mites, white beetles, gypsy moths, bark beetles, nematodes,
Thritips, etc.) as well as brown weevils,
It has a control effect at low concentrations against a wide range of pests, including storage pests such as the snail moth, sanitary pests such as flies, mosquitoes, and cockroaches. The second feature of the composition of the present invention is that it is extremely effective against insect pests that have already developed resistance to organophosphorus insecticides and acaricides and/or carbamate insecticides and acaricides. It is effective, and it is also difficult to develop chemical resistance against various insect pests. The third feature of the composition of the present invention is that it has fast-acting properties that are not found in general organophosphorus insecticides and acaricides and carbamate insecticides and acaricides. It is possible to make pests fall and turn upside down. Furthermore, the fourth feature is that it has low toxicity to fish and warm-blooded animals and has no risk of causing environmental pollution, making it an extremely ideal insecticide and acaricide. When actually applying the composition of the present invention, it is sufficiently effective even if the composition itself is diluted.
In order to make it easier to use as a pesticidal agent, it is common to mix various carriers into a preparation, dilute it as necessary, and apply it. In formulating the composition of the present invention, emulsions, wettable powders,
It can be prepared into any dosage form such as powders, fine granules, granules, oils, aerosols, heated fumigants (mosquito coils, electric mosquito repellents, etc.), fogging agents, non-heated fumigants, poison baits, etc. It can be used for various purposes depending on the purpose. The composition of the present invention has high stability against light, heat, oxidation, etc., but if necessary, antioxidants or ultraviolet absorbers, such as phenol derivatives such as BHT and BHA, bisphenol derivatives, A composition with stable effects can also be obtained by adding an appropriate amount of arylamines or benzophenone compounds such as phenyl α-naphthylamine, phenyl β-naphthylamine, and a condensate of phenetidine and acetone as a stabilizer. Furthermore, for the purpose of obtaining a multipurpose agricultural chemical, the composition of the present invention may be used by adding an attractant, a repellent, a fungicide, a herbicide, a plant growth regulator, a fertilizer, etc. The composition ratio of the compound of general formula [] and the synergist in the composition of the present invention is 99:1 to 1:99, preferably 1:20 to 1:1. When the composition of the present invention is formulated, the active ingredient concentration is 1 to 20% for emulsions and 0.1 to 1 for aerosols.
%, 0.1 to 5% for mosquito coils, 0.1 to 5% for electric heating plate fumigation compositions (both weight %)
is desirable. Next, some examples of formulations in which the composition of the present invention is used as an agrochemical or an epidemic prevention drug will be shown, but the present invention is not limited to these. All "parts" indicate "parts by weight." Formulation Example 1 Compounds in Table 1 above (“Compound No. 1 to 94
(same hereinafter) 3 parts, 9 parts of a synergist,
Emulsifier Solpol SM-200 (Toho Chemical brand name) 10
1 part and 78 parts of xylene were stirred and mixed to form an emulsion. Formulation Example 2 1 part of the compound in Table 1 and 5 parts of the synergist were mixed with 20 parts of acetone.
After adding 94 parts of clay for powder, the mixture was stirred to evaporate the acetone and form a powder. Formulation Example 3 Add 0.1 part of the compound shown in Table 1 and 0.5 part of a synergist and dissolve in white kerosene to make an oil solution to make 100 parts. Formulation Example 4 Mix and dissolve 0.1 part of the compound shown in Table 1, 0.3 part of the synergist, 7 parts of xylene, and 7.6 parts of deodorized kerosene. Fill the aerosol container with this and attach the valve. Propellant (liquefied petroleum gas) through the valve part 80
The mixture is pressurized and filled to form an aerosol. Formulation example 5 0.3g of the compound in Table 1, 0.9g of synergist, BHT0.3
g, dissolved in 20 ml of methanol, stirred and mixed uniformly with 99.4 of mosquito coil carrier (a mixture of tab powder, lees powder, and wood flour in the ratio of 3:5:1), evaporated the methanol, and then dissolved in water. Add 150ml, mix well, mold and dry to make mosquito coils. Formulation example 6 0.2g of the compound in Table 1 and 1.0g of the synergist
Add 0.2g of BHT, dissolve in chloroform, and
Uniformly adsorb it on a 0.3 cm paper and heat it on an electric heating plate to make a fiber fumigation composition. Formulation Example 7 Add 10 parts of a synergist to 5 parts of the compound in Table 1, add 5 parts of Emulsified Solpol 355TLL (trade name of Toho Chemical), stir well, and add 300 mesh of diatomaceous earth 80
1 part and thoroughly stirred and mixed in a Raikai machine to prepare a wettable powder. Formulation example 8 Add 5 parts of synergist to 1 part of the compound in Table 1, 90 parts of clay, Toyolignin CT (Toyobo registered trade name)
Add 4 parts, mix well, add water, stir and mix, granulate using a granulator, and dry to obtain granules. Formulation example 9 0.1 part of the compound in Table 1, 0.3 part of synergist, deodorized kerosene
Mix 11.6 parts of emulsifier Atmos 300 (trade name registered at Atlas Chemical Co.) with 1 part of emulsifier, add 50 parts of pure water, and emulsify. This is filled into an aerosol container with 37 parts of a 3:1 mixture of deodorized butane and deodorized propane to form a water-based aerosol. Next, the names of specific pests to which the insecticide/acaricide of the present invention can be applied are listed [scientific name - (Japanese name)]. 1 Hemiptera Nephotettix cincticeps Uhler Sogatella furcifera Horvath Nilaparvata lugens Sta゜l Laodelphax striatellus Fallen Eurydema rugosum Motschulsky Eysarcoris parvus Uhler Halyomorpha mista Uhler Lagynotomus elongatus Dallas Nezara viridula Linne′ Cletus trigonus Thunberg′ Stephanitis nashi Esaki et Takeya Stephanitis pyrioides Scott Psyllapyrisuga Fo¨rster PSYLLAMALI SCHMIDBERG'ER (apple scalp TWOOD (Onishitsu Konazisis) APHIS GOSSYPII GLOVER (Wataa Bram) BREVICORYNE BRASSICAE LINNE ' Aphids) Rhopalosiphum maidis Fitch Icerya purchasi Maskell Planococcus citri Risso Unaspis yanonensis Kuwana 2 Lepidoptera Canephora asiatica Staudinger Spulerina astaurcta Me yrick ( Phyllomycter ringoneella Matsumura
(Plutella xylostella Linn′e) Promalactis inopisema Butler (Boll moth) Adoxophyes orana Fischer von
Ro¨slerstamm Bactra furfuran′a Haworth Leguminivora glycinivorella Matsumura
Cnaphalocrocis medinalis Guene′e Etiella zinckenella Treitschke Ostrinia furnacalis Guene′e Pleurophya derogata Fabricus Hyphantria cunea Drury Abraxas miranda Butler ) Lymantria dispar japonica Motschulsky
(Gypsy moth) Phalera fiavescens Bremer et Gray (Gypsy moth) Agrotis segetum Denis et Schiffer
mu¨ller Helicoverpa armigera Hu¨bner Pseudaletia separata Walker Mamestra brassicae Linne′ Plusia nigrisigna Walker Spodoptera litura Fablicirs Parnara guttata Bremer et Gray Pieris rapae crucivora Boisduval Chilo suppressalis Walker 3 Coleoptera Melanotus fortnumi Cande'ze Anthrenus verbasci Lunne' Tenebroides mauritanicus Linne' Lyctus brunneus Stephens Henosepilachna vigintioctopunctata
Fablicius Monochamus alternatus Hope Xylotrechus pyrrhoderus Bates Aulacophora femoralis Motschlusky Oulema oryzae Kuwayama Phyllotreta striolata Fablicius Callosobruchus chinensis Linne' Adzuki bean weevil) Echinocnemis SQUAMEUS BILLBERG (Sitophilus) Sitophilus Oryzae Linne '(Coco Sleep) Apoderus Erythrogaster Vollenhoven Anomala Cuprea Hope (Douganebui) Popillia Japonica Newman (Mame Kogane) 4 Hymenoptera (Siminoid) ATHALIA ROSAE japonensis Rohwer Arge similis Vollenhoven Arge pagana Panzer 5 Piptera Tipula aino Alexander Culex pipiens fatigans Wiedemann Aedes aegypti Linne′ Asphondylia SP. (Dazes Sayata Mabae) HYLEMYA ANTIQUA MEIGEN (Tanegitama) HYLEMYA PLATURA MEIGEN (Tanebae) Musca Domestica Vicina Macquart AE Coquillett (Urimibae) CHLOROPS ORYZAE MATSUMURA (Inakarabae) Agromyza ORYZAE MUNAKATA 6 SIPHONAPTERA (Ptera) Pulex irritans Linne′ (human flea) Williams 8 Anoplura Pediculus humanus corporis De Geer Phthirus pubus Linn'e Haematopinus eurystrnus Nitzsh 9 Psocoptera Trogium pulsatsrium Lunne' Liposcelis bostrychophil us Badonnel ( 10 Orthoptera (Orthoptera) Gryllotalpa africana palisot de Beauvois
Locusta migratoria danica Linne′ Oxya yezoensis Shiraki 11 Dictyoptera Blattella germanica Linne′ Periplaneta fuliginosa Serville 12 Acarina Boophilus microplus Canestrini Rhizoglyphis echinophus Fumouze et
Robin Next, the excellent effects of the composition of the present invention as an insecticide/acaricide will be explained in detail by giving test examples. Test example 1 Effect on German cockroaches.
A solution of the compound shown in the table at a predetermined concentration in acetone was dropped and air-dried to produce a dry film. Separately, in the same manner, an acetone solution containing a mixture of the compounds shown in Table 1 and the synergist S-421 at a ratio of 1:3 at a predetermined concentration in acetone was added dropwise and air-dried to prepare a dry film of the compound.
Apply butter to the inner wall of a waist-high shear and release 10 female adult cockroaches per shear, calculate the mortality rate after 24 hours, and calculate the LD-50 value for each compound alone and for the compound and synergist mixture. I asked for it. In the case of any compound, S-
The efficacy was higher when 421 was mixed, and the activity was more than doubled. Test Example 2 Effect on Spodoptera vulgaris Put 3rd instar larvae of Spodoptera vulgaris in a polyethylene cup with a diameter of 10 cm, and prepare an emulsion of the compound shown in Table 1 alone or a mixture of the compound and a synergist at a ratio of 1:2 according to Formulation Example 1. The solution was prepared, diluted with water to a predetermined concentration, and sprayed directly onto the larvae using a spray tower at 2 ml per cup. Immediately give artificial feed,
After 24 hours, the mortality rate of each insect was determined and the LC-50 value was calculated. Compared to the case of each compound alone, when a synergist was mixed, an increase in efficacy of more than twice was observed in all combinations. Test Example 3 Effect on spider mites Two-spotted spider mite larvae were released onto a green bean leaf disk with a diameter of 15 mm, and the same emulsion as in Test Example 2 was sprayed.The LC-50 value of each was determined and the effects were compared, and the results are shown in Table 1. The LC-50 value of the compound alone and the LC-50 value when the synergist was added were less than half that of the latter, indicating a high synergistic effect. Test example 4 Campbell's turntable method (Soap and Sanitary Chemicals Vol. 4 No. 6 p. 119 (1938))
Using 20 adult houseflies (female), an oil solution containing the compound shown in Table 1 alone and an oil solution containing the compound and a synergist in a ratio of 1:3 were prepared according to Formulation Example 3. Spray 1 ml of KT-50 to determine the time it takes for half of the house flies tested to fall and roll over (hereinafter referred to as "KT-50").
(abbreviated as "value") and compared them. In the case of any compound, the KT-50 value of the oil with the synergist added was less than half that of the compound alone, and the insecticidal rate could be accelerated. Test Example 5 Compound alone and synergist S- shown in Table 1
421 was prepared according to Formulation Example 5. Twenty female Culex Culex mosquitoes were released into a glass cylinder with a diameter of 20 cm and a height of 43 cm, and after acclimatization, each mosquito coil was lit and smoked in the cylinder for 2 minutes, and the fall and roll time of the Culex Culex adults was investigated. The number of dead insects was counted after 24 hours by placing the rolling insects in a pre-prepared waist-high chalet along with cotton soaked in 5% sugar water. The results are shown in Table 2 below. KT−50 in this table
As is clear from the values, the insecticidal rate of each compound when mixed with S-421 was faster than when each compound was used alone.
【表】
試験例 ６
製剤例１に準じて作つた前記第１表の各化合物
単独の協力剤Ｓ−421との混合乳剤を水で希釈し
有効成分で合計30ppmとした。一方化合物単独の
乳剤については有効成分で30ppmとなるように水
で希釈した。これらを１／１万アールポツトに移
植した４葉の水稲苗に散布し風乾後、稲を金網円
筒でおおい、ヒメトビウンカ雌成虫を10頭あて放
ち、24時間後生死虫を調査し死虫率を算出した。
結果を下記の第３表に示す。この表から明らかな
ように、混合乳剤は化合物単独の場合よりもいず
れも高い効果を示し高い相剰効果をもたらすこと
が明らかである。[Table] Test Example 6 A mixed emulsion of each of the compounds listed in Table 1 above and the synergist S-421 prepared according to Formulation Example 1 was diluted with water to give a total of 30 ppm of active ingredients. On the other hand, an emulsion containing a single compound was diluted with water to give an active ingredient concentration of 30 ppm. These were sprayed on four-leaf rice seedlings transplanted into 1/10,000 are pots, and after air-drying, the rice was covered with a wire mesh cylinder and 10 female adult brown planthoppers were released. After 24 hours, live and dead insects were examined to calculate the mortality rate. did.
The results are shown in Table 3 below. As is clear from this table, it is clear that the mixed emulsion exhibits higher effects than the compound alone and brings about a high mutual effect.
【表】【table】
【表】
であつた。
試験例に用いた協力剤Ｓ−421以外の前記協力
剤も、これらの試験例と同様の方法で試験した結
果ほゞ同じような殺虫ダニ効果が得られた。[Table] It was.
The above-mentioned synergists other than the synergist S-421 used in the test examples were tested in the same manner as in these test examples, and as a result, almost the same insecticidal and acaricidal effects were obtained.
Claims (1)
置換フエニル基または４−位がハロゲン原子、低
級アルキル基、低級ハロアルキル基、低級アルコ
キシ基、低級ハロアルコキシ基、低級アルキルチ
オ基、シアノ基又はニトロ基で置換されたフエニ
ル基、４−位の外に更に３−位がハロゲン原子、
低級アルキル基又は低級アルコキシ基で置換され
たフエニル基もしくはメチレンジオキシ基で置換
されたフエニル基を、R1はメチル基またはエチ
ル基を、R2はメチル、エチル基またはイソプロ
ピル基を、R3は水素原子またはハロゲン原子を、
R4は水素原子、ハロゲン原子、炭素数１ないし
２の低級アルキル基または炭素数１ないし２の低
級アルコキシ基をそれぞれ表わす。Ｘは、酸素原
子または硫黄原子を表わす。］で表わされる２−
アリールエチルエーテルまたはチオエーテル誘導
体の１種または２種以上とオクタクロロジプロピ
ルエーテルを協力剤を含有してなる殺虫、殺ダニ
用組成物。[Claims] 1. General formula [In the formula, Ar is a lower alkyl-substituted naphthyl group, an unsubstituted phenyl group, a halogen atom at the 4-position, a lower alkyl group, a lower haloalkyl group, a lower alkoxy group, a lower haloalkoxy group, a lower alkylthio group, a cyano group, or a nitro group. a phenyl group substituted with, a halogen atom at the 3-position in addition to the 4-position,
A phenyl group substituted with a lower alkyl group or a lower alkoxy group or a phenyl group substituted with a methylenedioxy group, R 1 is a methyl group or ethyl group, R 2 is a methyl, ethyl group or isopropyl group, R 3 is a hydrogen atom or a halogen atom,
R 4 represents a hydrogen atom, a halogen atom, a lower alkyl group having 1 to 2 carbon atoms, or a lower alkoxy group having 1 to 2 carbon atoms, respectively. X represents an oxygen atom or a sulfur atom. ] 2-
An insecticidal and acaricidal composition comprising one or more arylethyl ether or thioether derivatives and octachlorodipropyl ether as synergists.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56162793A JPS5865204A (en) | 1981-10-14 | 1981-10-14 | Insecticidal and acaricidal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56162793A JPS5865204A (en) | 1981-10-14 | 1981-10-14 | Insecticidal and acaricidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5865204A JPS5865204A (en) | 1983-04-18 |
| JPH0231682B2 true JPH0231682B2 (en) | 1990-07-16 |
Family
ID=15761309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56162793A Granted JPS5865204A (en) | 1981-10-14 | 1981-10-14 | Insecticidal and acaricidal composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5865204A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002080308A (en) * | 2000-06-28 | 2002-03-19 | Earth Chem Corp Ltd | Insect pest control agent for animal |
| JP5066915B2 (en) * | 2006-04-03 | 2012-11-07 | 住友化学株式会社 | 1,3-benzdioxole compounds and uses thereof |
-
1981
- 1981-10-14 JP JP56162793A patent/JPS5865204A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5865204A (en) | 1983-04-18 |
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