JPH0231685B2 - - Google Patents
Info
- Publication number
- JPH0231685B2 JPH0231685B2 JP56160147A JP16014781A JPH0231685B2 JP H0231685 B2 JPH0231685 B2 JP H0231685B2 JP 56160147 A JP56160147 A JP 56160147A JP 16014781 A JP16014781 A JP 16014781A JP H0231685 B2 JPH0231685 B2 JP H0231685B2
- Authority
- JP
- Japan
- Prior art keywords
- phenoxybenzyl
- cis
- group
- trans
- ether
- 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 62
- 150000003568 thioethers Chemical class 0.000 claims description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 42
- 230000000895 acaricidal effect Effects 0.000 claims description 38
- 239000002917 insecticide Substances 0.000 claims description 35
- 239000000642 acaricide Substances 0.000 claims description 34
- -1 methylenedioxy Chemical group 0.000 claims description 34
- 239000002728 pyrethroid Substances 0.000 claims description 24
- XLOPRKKSAJMMEW-SFYZADRCSA-M (R,R)-chrysanthemate Chemical compound CC(C)=C[C@@H]1[C@@H](C([O-])=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-M 0.000 claims description 10
- 230000000749 insecticidal effect Effects 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 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
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims description 4
- 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
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims description 4
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 claims description 4
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 claims description 3
- RLLPVAHGXHCWKJ-IEBWSBKVSA-N (3-phenoxyphenyl)methyl (1s,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-IEBWSBKVSA-N 0.000 claims description 2
- SFHVXKNMCGSLAR-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C(O)=O)C1(C)C SFHVXKNMCGSLAR-UHFFFAOYSA-N 0.000 claims description 2
- 125000006183 2,4-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])*)C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- OWZREIFADZCYQD-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Br)Br)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-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
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 claims description 2
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 114
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 89
- 150000001875 compounds Chemical class 0.000 description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 230000015572 biosynthetic process Effects 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000010446 mirabilite Substances 0.000 description 16
- 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 16
- 235000019441 ethanol Nutrition 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 238000001816 cooling Methods 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 241000607479 Yersinia pestis Species 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000012280 lithium aluminium hydride Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 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 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 241001465977 Coccoidea Species 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- 239000012485 toluene extract Substances 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
- BBPATOFBGJZMJM-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)acetonitrile Chemical compound CSC1=CC=C(CC#N)C=C1 BBPATOFBGJZMJM-UHFFFAOYSA-N 0.000 description 3
- 241000238657 Blattella germanica Species 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
- 241000257226 Muscidae Species 0.000 description 3
- 241001556089 Nilaparvata lugens Species 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 241001454295 Tetranychidae Species 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 239000000073 carbamate insecticide Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 2
- 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
- GUOBCKNZNKTEHF-UHFFFAOYSA-N 1-chloro-4-(1-chloro-2-methylpropan-2-yl)benzene Chemical compound ClCC(C)(C)C1=CC=C(Cl)C=C1 GUOBCKNZNKTEHF-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
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- 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 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 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
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001466042 Fulgoromorpha Species 0.000 description 2
- 241001058150 Icerya purchasi Species 0.000 description 2
- 241000255777 Lepidoptera 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
- 241000721621 Myzus persicae Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000545593 Scolytinae Species 0.000 description 2
- 241000254152 Sitophilus oryzae Species 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 241001414989 Thysanoptera Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940024113 allethrin Drugs 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229960005286 carbaryl Drugs 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000007788 liquid 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
- 238000000034 method Methods 0.000 description 2
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing 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
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 2
- 229960000490 permethrin Drugs 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 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
- SBNFWQZLDJGRLK-RTWAWAEBSA-N (1R)-trans-phenothrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-RTWAWAEBSA-N 0.000 description 1
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
- 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
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- 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
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- VFEVXBKBGMAKME-UHFFFAOYSA-N butane;hydrobromide Chemical compound Br.CCCC VFEVXBKBGMAKME-UHFFFAOYSA-N 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000031902 chemoattractant activity Effects 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 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
- 238000003958 fumigation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 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
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting 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
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003986 organophosphate insecticide Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
- 229960003536 phenothrin Drugs 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
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 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
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 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
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000007306 turnover Effects 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
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、新規化合物である下記の一般式
〔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誘導体の1種または2種以
上と、ピレスロイド系殺虫.殺ダニ剤のうち1種
または2種以上を含有してなる殺虫.殺ダニ用組
成物に関する。
本発明で用いられるピレスロイド系殺虫.殺ダ
ニ剤としては下記の化合物があげられる。( )
内は一般名を示す。
〔d−2−シス(ペンタ−2′,4′−ジエニル)〕
−3−メチルシクロペンタ−2−エン−4−オー
ル−1−オニル d−トランス−クリサンセメー
ト(ピレトリン)
〔d−2−シス(ペンタ−2′,4′−ジエニル)〕
−3−メチルシクロペンタ−2−エン−4−オー
ル−1−オニル 〔d−トランス−ピレスレート
(ピレトリン)
〔d−2−シス−(ブタ−2′−エニル)〕−3−
メチルシクロペンタ−2−エン−4−オール−1
−オニル d−トランス−クリサンセメート(シ
ネリン)
〔d−2−シス(ブタ−2′−エニル)〕−3−メ
チルシクロペンタ−2−エン−4−オール−1−
オニル d−トランス−ピレスレート(シネリン
)
〔dl−2−アリル−3−メチルシクロペンタ−
2−エン−4−オール−1−オニル dl−シス,
トランス−クリサンセメート(アレスリン)
dl−2−(α−フルフリル)−3−メチルペンタ
−2−エン−4−オール−1−オニル dl−シ
ス,トランス−クリサンセメート(フレスリン)
6−クロロピペロニル dl−シス,トランス−
クリサンセメート(バースリン)
2,4−ジメチルベジル dl−シス,トランス
−クリサンセメート(ジメスリン)
N−(3,4,5,6−テトラハイドロフタル
イミド)メチル dl−シス、トランス−クリサン
セメート(ネオピナミン)
4−アリルベンジル dl−シス、トランス−ク
リサンセメート(ベナスリン)
2,6−ジメチル−4−アリルベンジル dl−
シス,トランス−クリサンセメート
5−ベンジル−3−フルフリル dl−シス,ト
ランス−クリサンセメート(レスメスリン)
5−プロパギル−2−フルフリル dl−シス,
トランス−クリサンセメート(フラメスリン)
5−ベンジル−3−フルフリルメチル d−
cis(IR,3S,E)2,2−ジメチル−3−(2−
オキソ、2,2,4,5−テトラヒドロチオフエ
ニリデンメチル)シクロプロパンカルボキシレー
ト(カデスリン)
dl−2−アリル−3−メチル−シクロペンタ−
2−エン−4−オール−1−オニル 2,2,
3,3−テトラメチル−シクロプロパンカルボキ
シレート(テラレスリン)
3−フエノキシベンジル クリサンセメート
(フエノスリン)
α−シアノ−3−フエノキシベンジル クリサ
ンセメート(S−2073)
α−シアノ−3−フエノキシベンジル 2,
2,3,3−テトラメチルシクロプロパンカルボ
キシレート(フエンプロパスリン)
3−フエノキシベンジル 2,2−ジメチル−
3−(2,2−ジクロロビニル)シクロプロパン
カルボキシレート(パーメスリン)
α−シアノ−3−フエノキシベンジル 2,2
−ジメチル−3−(2,2−ジクロロビニル)シ
クロプロパンカルボキシレート(サイパーメスリ
ン)
α−シアノ−3−フエノキシベンジル 2,2
−ジメチル−3−(2,2−ジブロモビニル)シ
クロプロパンカルボキシレート(デカメスン)
α−シアノ−3−フエノキシベンジル 2−
(p−クロルフエニル)−3−メチルブチレート
(フエンバレレート)
α−シアノ−3−フエノキシベンジル 2−
(2−クロロ−4−トリフエニルメチル−フエニ
ルアミノ)−3−メチルブチレート(フルバニリ
ネート)。
従来、農園芸殺虫剤および防疫用殺虫剤として
例えば、
S−〔1,2−ビス(エトキシカルボニル)エ
チル〕ジメチルホスホロチオエート(マラソン)
ジメチル−4−ニトロ−m−トリル−ホスホロ
チオエート(MEP)
ジエチル−2,3−ジヒドロ−3−オキソ−2
−フエニル−6−ピリダジニルホスホロチオエー
ト(ピリダフエンチオン)
ジエチル−2−イソプロピル−6−メチル−4
−ピリミジル−ホスホロチオエート(ダイアジノ
ン)
O,S−ジメチル−N−アセチルホスホロアミ
ドチオエート(アセフエート)
ジメチル−S−(N−メチルカルバモイルメチ
ル)ホスホロチオールチオエート(ジメトエー
ト)
1−ナフチルメチルカーバメート(NAC)
m−トリルメチルカーバメート(MTMC)
2−ジメチルアミノ−5,6−ジメチルピリミ
ジン−4−イル−ジメチルカーバメート(ピリマ
ー)
3−メチル−N−(メチルカルバモイロキシ)
チオアセトイミデート(ランネート)
等の殺虫剤が使用されてきた。これらの殺虫剤
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、これらの薬剤を多量に田畑に
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高い防除
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、ピレス
ロイド系殺虫および殺ダニ剤の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。
本発明の前記一般式〔〕に含まれる化合物の
代表例とそれらの物性を下記の第1表に示す。
The present invention provides novel compounds of 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 methyl or ethyl group, R 2 is a methyl group, 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. ] and pyrethroid insecticide. Insecticide containing one or more acaricides. This invention relates to a miticidal composition. Pyrethroid insecticide used in the present invention. Examples of acaricides include the following compounds. ( )
The numbers inside indicate common names. [d-2-cis(penta-2',4'-dienyl)]
-3-Methylcyclopent-2-en-4-ol-1-onyl d-trans-chrysansemate (pyrethrin) [d-2-cis(pent-2',4'-dienyl)]
-3-Methylcyclopent-2-en-4-ol-1-onyl [d-trans-pyrethrate (pyrethrin) [d-2-cis-(but-2'-enyl)]-3-
Methylcyclopent-2-en-4-ol-1
-onyl d-trans-chrysanthemate (cinerine) [d-2-cis(but-2'-enyl)]-3-methylcyclopent-2-en-4-ol-1-
onyl d-trans-pyrethlate (cinerine) [dl-2-allyl-3-methylcyclopenta-
2-en-4-ol-1-onyl dl-cis,
trans-chrysansemate (allethrin) dl-2-(α-furfuryl)-3-methylpent-2-en-4-ol-1-onyl dl-cis, trans-chrysansemate (phresrin) 6-chloropiperonyl dl- cis, trans-
Chrysanthemate (Versulin) 2,4-dimethylbenzyl dl-cis,trans-chrysanthemate (dimethrin) N-(3,4,5,6-tetrahydrophthalimido)methyl dl-cis,trans-chrysanthemate (neopinamine ) 4-Allylbenzyl dl-cis, trans-chrysanthemate (benathrine) 2,6-dimethyl-4-allylbenzyl dl-
cis,trans-chrysansemate 5-benzyl-3-furfuryl dl-cis,trans-chrysanthemate (resmethrin) 5-propargyl-2-furfuryl dl-cis,
Trans-chrysansemate (flamethrin) 5-benzyl-3-furfurylmethyl d-
cis(IR,3S,E)2,2-dimethyl-3-(2-
Oxo,2,2,4,5-tetrahydrothiophenylidenemethyl)cyclopropanecarboxylate (cadesrin) dl-2-allyl-3-methyl-cyclopenta-
2-en-4-ol-1-onyl 2,2,
3,3-Tetramethyl-cyclopropanecarboxylate (Telarethrin) 3-Phenoxybenzyl chrysanthemate (Phenothrin) α-cyano-3-phenoxybenzyl chrysanthemate (S-2073) α-cyano-3- Phenoxybenzyl 2,
2,3,3-tetramethylcyclopropanecarboxylate (phenpropane) 3-phenoxybenzyl 2,2-dimethyl-
3-(2,2-dichlorovinyl)cyclopropanecarboxylate (permethrin) α-cyano-3-phenoxybenzyl 2,2
-dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate (cypermethrin) α-cyano-3-phenoxybenzyl 2,2
-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate (decamesone) α-cyano-3-phenoxybenzyl 2-
(p-Chlorphenyl)-3-methylbutyrate (fenvalerate) α-cyano-3-phenoxybenzyl 2-
(2-chloro-4-triphenylmethyl-phenylamino)-3-methylbutyrate (fluvanillinate). Conventionally, agricultural and horticultural insecticides and epidemic prevention insecticides include, for example, S-[1,2-bis(ethoxycarbonyl)ethyl]dimethylphosphorothioate (Marathon), dimethyl-4-nitro-m-tolyl-phosphorothioate (MEP), diethyl-2 ,3-dihydro-3-oxo-2
-Phenyl-6-pyridazinyl phosphorothioate (pyridafenethione) Diethyl-2-isopropyl-6-methyl-4
-Pyrimidyl-phosphorothioate (Diazinon) O,S-dimethyl-N-acetylphosphoroamidothioate (acephenate) Dimethyl-S-(N-methylcarbamoylmethyl)phosphorothiolthioate (dimethoate) 1-Naphthylmethylcarbamate (NAC) ) m-Tolylmethylcarbamate (MTMC) 2-dimethylamino-5,6-dimethylpyrimidin-4-yl-dimethylcarbamate (pyrimer) 3-Methyl-N-(methylcarbamoyloxy)
Insecticides such as thioacetimidate (lannate) have been used. Some of these insecticides have excellent properties such as fast-acting, systemic migration, and gas effect, but they are not all satisfactory in terms of insecticidal spectrum, residual effectiveness, fish toxicity, and human toxicity. . Furthermore, as a result of the long-term use of these insecticides, pests 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 resistant to chemicals. Insecticides and carbamate insecticides are losing their practicality. Furthermore, environmental pollution of soil, rivers, etc. due to the use of large amounts of these chemicals in fields is a problem, and control using low dosages is desired. The novel compound of the present invention represented by the above general formula [] satisfies these requirements and can be used alone to kill insects. Although it has acaricidal activity, the present inventors further conducted various studies to obtain high pesticidal effects and reduce the amount of use of these compounds in actual situations, and as a result, the compounds represented by the general formula [] discovered that by applying one or more pyrethroid insecticides and acaricides in combination, the insecticidal spectrum is broadened and the insecticidal activity is synergistically enhanced compared to when applied alone. , completed the invention. Representative examples of the compounds included in the above 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】【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た本発明化合物の代
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−フエノキシ−4−フルオロベンジル 2
−(3,4−ジメチルフエニル)−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
−(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−(3−クロロフエ
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−(3−クロロフエニル)−4
−フルオロベンジル 2−(3,4−ジメチルフ
エニル)−2,3−ジメチルフチルエーテルおよ
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−(4−tert−ブ
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−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−5−フルオロベンジ
ル 2−(3,4−ジエチルフエニル)−2−メチ
ルプロピルエーテルおよびチオエーテル、3−
(3−フルオロフエノキシ)−4−フルオロベンジ
ル 2−(3−メトキシ−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−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−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−フエノキシ−4−フルオロベンジル 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)−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−2−フ
ルオロベンジル 2−(4−トリフルオロメチル
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−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−6−クロルベン
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−フエノ
キシ−6−フルオロベンジル 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−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−メ
チルフエニル)−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−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−メチル
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−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−tert−ブチルフエニル)−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−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−エチ
ルフエニル)−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−(4−エチルフエニル)−
2−エチルプロピルエーテル、3−フエノキシベ
ンジル 2−(3,4−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−(4−クロロ−3−メチルフエニル)−2
−メチルプロピルエーテル、3−フエノキシベン
ジル 2−(4−tert−ブチルフエニル)−2−エ
チルプロピルエーテル、3−フエノキシベンジル
2−(3,4−ジメチルフエニル)−2−メチル
プロピルエーテル、3−フエノキシベンジル 2
−(3−クロロ−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−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−3−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
−(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−(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、3−フエノキシベンジル
2−(4−フロロ−3−メチルフエニル)−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−3−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−フロロ−4−メチルフエニル)−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−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−ブロモ−4−メチルフエニル)
−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−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−(3,4−ジエチル−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−ジエチル−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−(4−イソプロピルフエニル)−2−メチ
ルプロピルエーテル、3−フエノキシベンジル
2−(4−イソプロピルフエニル)−2−エチルプ
ロピルエーテル、
3−フエノキシベンジル 2−(3,4−ジイ
ソプロピルフエニル)−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−
ジイソプロピルフエニル)−2−エチルプロピル
エーテル、3−フエノキシベンジル 2−(3,
4−ジ−ターシヤリーブチルフエニル)−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−ターシヤリーブチルフエニ
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−エチル−4−メチルフ
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−エチル−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−(4−エチル−3−
メチルフエニル)−2−メチルプロピルエーテル、
3−フエノキシベンジル 2−(4−エチル−3
−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−(4−ターシ
ヤリーブチル−3−メチルフエニル)−2−メチ
ルプロピルエーテル、3−フエノキシベンジル
2−(4−ターシヤリーブチル−3−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−(4−イソプロピル−3−
メチル−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−イソプ
ロピル−3−メチルフエニル)−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−フルオロベンジルブロマイド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)−2−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。
トルエンにて抽出し、トルエン抽出液を水洗し
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
応した。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
ルアルコール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セパラブルフラスコに装入し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。
n19.5 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℃/10cm
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)2.7g、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20.3
g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)2.7g、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分間加熱還流を続けた。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化リチウムアルミ
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%。
n20.4 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、アセトンで十分洗滌した。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酸性とし、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)ppm
(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20g/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
以下の順序に従つた合成した。
(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20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
洗滌し、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をスラスコに装入し、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。ベンゼン層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、2H)、7.0〜7.6(m、
4H)、11.3(broad 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の混合物の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
合成実施例 13
2−(4−メチルチオフエニル)−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) 4−メチルチオベンジルクロライドの合成
メチラール18.2gを1,2−ジクロルエタン
200mlに溶解し、水で冷却しながら無水塩化ア
ルミニウム61.4gを加えた。これにチオアニソ
ール24.8gを室温で滴下し、そのまま3時間か
きまぜ反応させた。反応終了後水に排出し、濃
塩酸を加えて固形物を溶解した後、ベンゼンに
て抽出し抽出液を水洗、希炭酸水素ナトリウム
水で洗浄し水洗した。その後芒硝で乾燥した
後、脱溶媒して30.7gの油状残渣を得た。
(2) (4−メチルチオフエニル)−アセトニトリ
ルの合成
水12gに青化ソーダ10.5gを溶解し、60℃に
加熱する。これにエタノール35mlに溶解した上
記(1)で得た油状物30.7gを滴下し、4時間リフ
ラツクスして反応させた。常法通り後処理し
て、ベンゼンを展開剤としてカラムクロマトグ
ラフイーにより分離して14.7gの(4−メチル
チオフエニル)−アセトニトリル(油状物)を
得た。
δccl4 2.37(S、3H)、3.56(S、2H)、7.16(S
、
4H)
(3) 1−(4−メチルチオフエニル)−1,1−ジ
メチルアセトニトリルの合成
合成実施例10の(1)と同様にして(4−メチル
チオフエニル)−アセトニトリル13.1gから
13.9gの目的物を得た。
δccl4 1.66(S、6H)、2.45(S、3H)、7.2〜7.6
(m、4H)
(4) 1−(4−メチルチオフエニル)−1−メチル
プロピオン酸の合成
カセイカリ5.0g、水5g、ジエチレングリ
コール20mlに1−(4−メチルチオフエニル)−
1,1−ジメチルアセトニトリル3.8gを加え、
130〜140℃で7時間反応させた。反応終了後冷
却して、水に排出し、ベンゼンで抽出した。水
層を濃塩酸で酸性化すると沈澱が析出した。こ
れをエーテルで抽出し、飽和食塩水水で洗浄
し、芒硝で乾燥して脱溶媒し、固体の1−(4
−メチルチオフエニル)−1−メチルプロピオ
ン酸を1.9g得た。
δアセトンd6 1.54(S、6H)、2.43(S、3H)、
7.0−7.5(m、4H)
(5) 2−(4−メチルチオフエニル)−1−メチル
プロピルアルコールの合成
常法通り水素化リチウムアルミニウムで還元
し1−(4−メチルチオフエニル)−1−メチル
プロピオン酸1.9gから目的のアルコール1.5g
を得た。
δccl4 1.26(S、6H)、2.39(S、3H)、3.38(S
、
2H)、7.0〜7.4(m、4H)
合成実施例 14
2−(4−クロロフエニル)−2−メチルプロピ
ルチオールの合成
以下の順序に従つて合成した。
(1) 2−(4−クロロフエニル)−2−メチルプロ
ピルトシレートの合成
2−(4−クロロフエニル)−2−メチルプロ
ピルアルコール10.0gとp−トルエンスルホニ
ルクロライド10.8gにピリジン20mlを加え、50
〜55℃で1hrで反応させた。反応物を100gの氷
水に排出し、希塩酸で酸性化し、ベンゼンで抽
出した。ベンゼン層を飽和食塩水で洗浄した
後、芒硝で乾燥し、減圧下に溶媒を留去して
19.3gの白色固体残渣を得た。融点69〜71.5℃
δccl4 1.31(S、6H)、2.44(S、3H)、3.89(S
、
2H)、7.13(S、4H)、7.18〜7.60〔m、4H
(ABTYpe)〕
νKBr nax 1595、1480、1355、1175、970、825cm-1
(2) ビス−〔2−(4−クロロフエニル)−2−メ
チルプロピル〕ジスルフイツドの合成
(1)で得たトシレート13.0gと水硫化ソーダ
20.0g(70%品)および90%エタノール100ml
をかきまぜながらリフラツクス下3時間反応さ
せた。反応物を水に排出し、ベンゼンで抽出
し、ベンゼン層を水洗した後、芒硝で乾燥し
た。減圧下にベンゼンを留去し、液状残渣7.9
gを得た。ベンゼン−ヘキサン(1:3)の混
合溶媒を用い、これをシリカゲルカラムクロマ
トグラフイーにより分離し、目的物5.3g(油
状)を得た。
νfilm nax 2950、1500、1410、1395、1380、1120、
1105、1020、830、755cm-1
δccl4 1.31(S、6H)、2.81(S、2H)、7.18(d
、
4H)
元素分析
C H S Cl
計算値% 60.17 6.01 16.06 17.76
測定値% 59.06 6.07 16.55 17.56
(3) 2−(4−クロロフエニル)−2−メチルプロ
ピルチオールの合成
乾燥エーテル25mlに水素化リチウムアルミニ
ウム0.095gを懸濁し、これに10mlのエーテル
に溶解したビス−〔2−(4−クロロフエニル)
−2−メチルプロピル〕ジスルフイツド1.0g
を滴下し、還流下2時間反応させた。反応終了
後、反応物を水に排出し、15%希硫酸を加え、
ベンゼンにて抽出した。ベンゼン層を飽和食塩
水で洗浄し、芒硝で乾燥後、減圧下溶媒を留去
して、液状残渣1.0gを得た。
νfilm nax 2965、2570、1495、1405、1390、1370、
1105、1020、830cm-1
δccl4 0.80(t、1H)、1.33(S、6H)、2.68(d
、
2H)、7.23(S、4H)
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1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、水稲、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の特長としては、魚類や温血動物に
対して低毒性であり、環境汚染をひきおこすおそ
れのないなどの多くのすぐれた特長を有し、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
ピレスロイド系殺虫.殺ダニ剤との組成比は99:
1〜1:99好ましくは10:1〜1:1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%、粉剤では0.3〜3%、水和剤で
は5〜50%、粒剤では0.5〜50%、エアゾールで
は0.1〜1%(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。
製剤例中の「ピレスロイド系殺虫.殺ダニ剤」
は前記本明細書記載の化合物を示す。同じく「第
1表の化合物」は第1表記載化合物のいずれか1
種を示す。
製剤例 1
第1表の化合物5部、ピレスロイド系殺虫.殺
ダニ剤5部、乳化剤ソルポールSM−200(東邦化
学商品名)10部、キシレン70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、ピレスロイド系殺虫.殺
ダニ剤1部をアセトンに溶解し、粉剤用クレー98
部を加えたのち撹拌し、アセトンを蒸発せしめて
粉剤とする。
製剤例 3
第1表の化合物5部にピレスロイド系殺虫.殺
ダニ剤5部を加え、乳化剤ソルポール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75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 4
第1表の化合物3部にピレスロイド系殺虫.殺
ダニ剤3部を加え、クレー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、更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 5
第1表の化合物1部にピレスロイド系殺虫.殺
ダニ剤1部を加え、白灯油等に溶解し全体を100
部として油剤とする。
製剤例 6
第1表の化合物0.2gにピレスロイド系殺虫.
殺ダニ剤0.2gに協力剤0.9g、BHT0.3gを加え
メタノール20mlに溶解し、各々蚊取線香用担体
(タブ粉、粕粉、木粉を3:5:1の割合で混合
したもの)99.4g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 7
第1表の化合物0.1g、ピレスロイド系殺虫.
殺ダニ剤0.1g、協力剤1.0gにBHT0.2gを加え、
クロロホルムに溶解し、厚さ0.3cmの紙に吸着
させ、電熱板上加熱繊維燻蒸組成物とする。
製剤例 8
第1表の化合物0.1部、ピレスロイド系殺虫.
殺ダニ剤0.1部、協力剤0.3部、キシロール7部、
脱臭灯油7.5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
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 9
第1表の化合物0.1部、ピレスロイド系殺虫.
殺ダニ剤0.1部、協力剤0.3部、脱臭灯油11.5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。これに臭化ブタン、脱臭プロパン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 Falle′n(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)
Halyomorphamista 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 Thunber′g(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)
Psylla pyrisuga Fo¨rster(ナシキジラミ)
Psylla mali Schmidberger(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 Linn′e(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)
Phyllonorycter 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 furfura′na Haworth(イグサシンム
シガ)
Leguminivora glycinivorella Matsumura
(マメシンクイガ)
Cnaphalocrocis medinalis Guen′ee(コブノ
メイガ)
Etiella zinckenella treitschke(シロイチモ
ジマダラメイガ)
Ostrinia furnacalis Guen′ee(アワノメイ
ガ)
Pleurophya derogata Fabricius(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 Linn′e(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 guttataBremer 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 Lunn′e(ヒメマルカツ
オブシムシ)
Tenebroides mauritanicus Linn′e(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(イネドロオム
シ)
Phyllotreta striolata Fablicus(キスジノミ
ハムシ)
Callosobruchus chinensis Linn′e(アズキゾ
ウムシ)
Echinocnemis squameus Billberg(イネゾ
ウムシ)
Sitophilus oryzae Linn′e(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 Linn′e(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(隠翅目)
Pulex irritans Linn′e(ヒトノミ)
Xenopsylla cheopis Rothschild(ケオプス
ネズミノミ)
Ctenocephalides Canis Curtis(イヌノミ)
7 Thysanophera(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 pubis Linn′e(ケジラミ)
Haematopinus eurysternus Nitzsh(ウシジ
ラミ)
9 Psocoptera(チヤムタテムシ目)
Trogium pulsatsrium Lunn′e(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 Linn′e(トノサ
マバツタ)
Oxya yezoensis Shiraki(コバネイナゴ)
11 Dictyoptera(網翅目)
Blattella germanica Linn′e(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 cinnabarinus Boisduval(ニセ
ナミハダニ)
Tetranychus urticae Koch(ナミハダニ)
Rhizoglyphus 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
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ピレスロイド系殺
虫.殺ダニ剤を1:1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第1表の各化合物単独の場合
及び同化合物とピレスロイド系殺虫.殺ダニ剤と
の混合の場合の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ピ
レスロイド系殺虫.殺ダニ剤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
及び化合物とピレスロイド系殺虫.殺ダニ剤を
1:1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てピレスロイド系
殺虫.殺ダニ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
ダニ成虫を放ち、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
ピレスロイド系殺虫.殺ダニ剤を加えた場合の
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
感受性ヒメトビウンカに対する効果
水稲稚苗(本葉2−3枚)を直径5cmのポツト
に水耕栽培し、これを製剤例1で示した方法によ
り得られた各供試化合物の10ppm濃度の薬液を噴
霧器にてそれぞれ3ml/ポツトを用いて処理し
た。風乾後、苗を金網円筒でおおい、感受性ヒメ
トビウンカ(茅ケ崎産)の雄成虫をポツト当り10
頭放ち、25℃の室内に静置した。処理24時間後、
生死虫数を調査し死虫率を算出した。結果は3連
平均値で第2表に示した。[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 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, representative examples of the compounds of the present invention thus obtained are shown, but of course the compounds of the present invention are not limited to these examples. In addition, when R 1 and R 2 are different groups in the general formula [], the compound of the present invention has an asymmetric carbon and optical isomers exist, but these optical isomers and mixtures of these components are included. are doing. 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-phenoxy-4-fluorobenzyl 2
-(3,4-dimethylphenyl)-2-methylpropyl ether and thioether, 3-(4-fluorophenoxy)-4-fluorobenzyl 2
-(4-methoxyphenyl)-2-methylpropyl 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-(3-chlorophenoxy)-4-fluorobenzyl 2-(4-chlorophenyl)-2-methylpropyl ether and thioether, 3-(3-chlorophenyl) -4
-fluorobenzyl 2-(3,4-dimethylphenyl)-2,3-dimethylphthyl 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-(4-tert-butylphenyl)-2-methyl Propyl 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-fluorobenzyl 2-(4-bromophenyl)-2-methylpropyl ether and thioether, 3-Phenoxy-5-fluorobenzyl 2-(3,4-diethylphenyl)-2-methylpropyl ether and thioether, 3-
(3-fluorophenoxy)-4-fluorobenzyl 2-(3-methoxy-4-methylphenyl)-
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-phenoxy-4-fluorobenzyl 2-(4-methylthiophenyl)-2
- methylpropyl ether and thioether,
3-phenoxy-4-fluorobenzyl 2-
(4-Methylphenyl)-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-
Methyl propyl ether and thioether, 3
-Phenoxy-5-fluorobenzyl 2-(4
-chlorophenyl)-2-methylpropyl ether and thioether, 3-phenoxy-2-fluorobenzyl 2-(4-trifluoromethylphenyl)-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-6-chlorobenzyl 2-(4 -Methylphenyl)-2-methylpropyl ether and thioether, 3-phenoxy-6-fluorobenzyl 2-(4-methylphenyl)-2-methylpropyl ether and thioether, 3-phenoxy-4-fluorobenzyl 2-(3,4 -methylenedioxyphenyl)-2-methylpropyl ether and thioether, 3-phenoxybenzyl 2-(4-methylphenyl)-2-methylpropyl ether,
3-Phenoxybenzyl 2-(4-bromophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4-methylphenyl)-2-methylpropyl ether, 3-
Phenoxybenzyl 2-(3,4-dibromophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-chlorophenyl)-
2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-tert-butylphenyl)-2-
Methylpropyl ether, 3-phenoxybenzyl 2-(4-fluorophenyl)-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-ethylphenyl)-2-methylpropyl ether, 3
-Phenoxybenzyl 2-(4-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-chloro-4-fluorophenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2 -(4-ethylphenyl)-
2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dichlorophenyl)-2-
Ethylpropyl ether, 3-phenoxybenzyl 2-(4-chloro-3-methylphenyl)-2
-Methylpropyl ether, 3-phenoxybenzyl 2-(4-tert-butylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-dimethylphenyl)-2-methylpropyl ether , 3-phenoxybenzyl 2
-(3-chloro-4-methylphenyl)-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-chloro-3-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2
-(4-chlorophenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4
-dimethylphenyl)-2-ethylpropyl 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, 3-phenoxybenzyl
2-(4-fluoro-3-methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-fluoro-3-methylphenyl)-2-
Ethylpropyl ether, 3-phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-2
-Methylpropyl ether, 3-phenoxybenzyl 2-(3-fluoro-4-methylphenyl)-
2-ethylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-methylphenyl)
-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-bromo-4-methylphenyl)
-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-diethyl-phenyl)-
2-Methylpropyl ether, 3-phenoxybenzyl 2-(3,4-diethyl-phenyl)-2-
Ethylpropyl ether, 3-phenoxybenzyl 2-(4-isopropylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl
2-(4-isopropylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,4-diisopropylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3 ,4-
diisopropylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(3,
4-Di-tert-butylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3,4-di-tert-butylphenyl)-2-ethylpropyl ether, 3-phenoxy Benzyl 2-(3-ethyl-4-methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(3-ethyl-4-methylphenyl)-2-ethylpropyl ether, 3
-Phenoxybenzyl 2-(4-ethyl-3-
methylphenyl)-2-methylpropyl ether,
3-phenoxybenzyl 2-(4-ethyl-3
-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-tert-butyl-3-methylphenyl)-2-methylpropyl ether, 3-phenoxybenzyl
2-(4-tert-butyl-3-methylphenyl)-2-ethylpropyl ether, 3-phenoxybenzyl 2-(4-isopropyl-3-
Examples include methyl-phenyl)-2-methylpropyl ether, 3-phenoxybenzyl 2-(4-isopropyl-3-methylphenyl)-2-ethylpropyl ether, and the like. Next, the method for producing the compound represented by the general formula [] of the present invention 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-fluorobenzyl bromide 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)-2-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 extraction with toluene and washing the toluene extract with water, it was dried with Glauber's salt. The crude ether obtained by distilling toluene off under reduced pressure was passed through a silica gel column.
100g column chromatography (developing solvent:
Purification was performed using toluene/n-hexane (1:1) to obtain 2.7 g (theoretical yield: 71%) of the desired pure ether. 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 discharged into 500 ml of water, extracted with benzene, the benzene extract was washed with water, and then dried with Glauber's salt. The crude ether obtained by distilling off benzene under reduced pressure was separated and purified by column chromatography on 250 g of silica gel (developing solvent: toluene/n-hexane 1:1) to obtain the desired ether.
7.27 g (77% theoretical yield vs. consumed 4-chlorneofyl chloride) was obtained. 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 19.5 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
While keeping 20 g of H 2 O and 2 g of triethylbenzylammonium bromide at 80°C to 90°C, add methyl iodide (1.2 g to arylacetonitrile).
molar ratio) was added dropwise over 1 to 2 hours. 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,
Tarshiary. 46g of butyl chloride 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./28 mmHg). (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℃/10cm
Hg) was obtained. (3) Add 2.7 g of magnesium (turnings) and a small amount of iodine as a catalyst to 100 ml of dry tetrahydrofuran, and add 20.3 g of 2-(4-chlorophenyl)-2-methyl-1-chloropropane under reflux under heating.
g was added dropwise over 30 minutes, and heating and refluxing was continued for 10 hours. After cooling to room temperature, oxygen gas was blown in for 1 hour. Next, after adding a saturated aqueous ammonium chloride solution, most of the tetrahydrofuran was distilled off under reduced pressure, and the mixture was extracted with toluene. Toluene was distilled off under reduced pressure to obtain crude alcohol. Then, recrystallization from cold hexane yields the desired 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 2.7 g of magnesium (turnings) and a small amount of iodine as a catalyst, and 17 g of methyl iodide was slowly added dropwise. After the dropwise addition was completed, heating and refluxing was continued for 30 minutes. 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. Furthermore, after heating under reflux for 3 hours, 6N
-20 ml of HCl was added dropwise over 30 minutes. Then, the temperature was raised and the mixture was heated under reflux for 7 hours. 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 the desired 2-(3,4-methylenedioxyphenyl)-2-methyl-3-
19.2 g of butanone was obtained. (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 hydride in tetrahydrofuran to obtain the desired 2-(3,4- Methylenedioxyphenyl)-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 20.4 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 made acidic 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) ppm (3) A solution of 20 g of 2-(4-difluoromethoxyphenyl)-2-methylpropionic 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 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 Synthesis was performed 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 20 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 in 30 ml of ethanol in 8.8 g of NaCN and 9.0 g of water at 70-80℃
(for 30 minutes). 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. The benzene layer 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. Then, the aqueous layer was diluted with concentrated hydrochloric acid, pH 4.6, 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, 2H), 7.0-7.6 (m,
4H), 11.3 (broad S, 1H) (3) A solution of 3.0 g of 2-(4-fluorophenyl)-2-methylbutyric acid/10 ml of tetrahydrofuran in a mixture of 20 ml of tetrahydrofuran and 0.5 g of lithium aluminum hydride was added dropwise at 40°C. did. 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 Synthesis Example 13 2-(4-Methylthiophenyl)-2-methylpropyl alcohol Synthesized according to the following sequence. (1) Synthesis of 4-methylthiobenzyl chloride 18.2g of methylal was added to 1,2-dichloroethane.
The solution was dissolved in 200 ml, and 61.4 g of anhydrous aluminum chloride was added while cooling with water. To this, 24.8 g of thioanisole was added dropwise at room temperature, and the mixture was stirred for 3 hours to react. After the reaction was completed, the mixture was poured into water, concentrated hydrochloric acid was added to dissolve the solid matter, and then extracted with benzene. The extract was washed with water, diluted sodium bicarbonate water, and water. After drying with Glauber's salt, the solvent was removed to obtain 30.7 g of an oily residue. (2) Synthesis of (4-methylthiophenyl)-acetonitrile Dissolve 10.5 g of soda cyanide in 12 g of water and heat to 60°C. To this was added dropwise 30.7 g of the oil obtained in (1) above dissolved in 35 ml of ethanol, and the mixture was refluxed for 4 hours to react. The residue was worked up in a conventional manner and separated by column chromatography using benzene as a developing agent to obtain 14.7 g of (4-methylthiophenyl)-acetonitrile (oil). δ ccl4 2.37 (S, 3H), 3.56 (S, 2H), 7.16 (S
,
4H) (3) Synthesis of 1-(4-methylthiophenyl)-1,1-dimethylacetonitrile From 13.1 g of (4-methylthiophenyl)-acetonitrile in the same manner as in (1) of Synthesis Example 10.
13.9g of the target product was obtained. δ ccl4 1.66 (S, 6H), 2.45 (S, 3H), 7.2-7.6
(m, 4H) (4) Synthesis of 1-(4-methylthiophenyl)-1-methylpropionic acid 1-(4-methylthiophenyl)-
Add 3.8g of 1,1-dimethylacetonitrile,
The reaction was carried out at 130-140°C for 7 hours. After the reaction was completed, the mixture was cooled, poured into water, and extracted with benzene. When the aqueous layer was acidified with concentrated hydrochloric acid, a precipitate was deposited. This was extracted with ether, washed with saturated brine, dried with Glauber's salt and desolvented, and the solid 1-(4
1.9 g of -methylthiophenyl)-1-methylpropionic acid was obtained. δ acetone d6 1.54 (S, 6H), 2.43 (S, 3H),
7.0−7.5 (m, 4H) (5) Synthesis of 2-(4-methylthiophenyl)-1-methylpropyl alcohol Reducing with lithium aluminum hydride in the usual manner to produce 1-(4-methylthiophenyl)-1- 1.5g of desired alcohol from 1.9g of methylpropionic acid
I got it. δ ccl4 1.26 (S, 6H), 2.39 (S, 3H), 3.38 (S
,
2H), 7.0 to 7.4 (m, 4H) Synthesis Example 14 Synthesis of 2-(4-chlorophenyl)-2-methylpropylthiol Synthesis was performed according to the following sequence. (1) Synthesis of 2-(4-chlorophenyl)-2-methylpropyl tosylate Add 20 ml of pyridine to 10.0 g of 2-(4-chlorophenyl)-2-methylpropyl alcohol and 10.8 g of p-toluenesulfonyl chloride.
The reaction was carried out at ~55°C for 1 hr. The reaction was drained into 100 g of ice water, acidified with dilute hydrochloric acid, and extracted with benzene. The benzene layer was washed with saturated brine, dried with Glauber's salt, and the solvent was distilled off under reduced pressure.
19.3 g of white solid residue was obtained. Melting point 69-71.5℃ δ ccl4 1.31 (S, 6H), 2.44 (S, 3H), 3.89 (S
,
2H), 7.13 (S, 4H), 7.18-7.60 [m, 4H
(ABTYpe)] ν KBr nax 1595, 1480, 1355, 1175, 970, 825cm -1 (2) Synthesis of bis-[2-(4-chlorophenyl)-2-methylpropyl]disulfide Tosylate 13.0 obtained in (1) g and sodium hydrogen sulfide
20.0g (70% product) and 100ml of 90% ethanol
The mixture was reacted for 3 hours under reflux while stirring. The reaction product was discharged into water, extracted with benzene, and the benzene layer was washed with water and then dried with Glauber's salt. Benzene was distilled off under reduced pressure, leaving a liquid residue of 7.9
I got g. This was separated by silica gel column chromatography using a mixed solvent of benzene-hexane (1:3) to obtain 5.3 g (oil) of the target product. ν film nax 2950, 1500, 1410, 1395, 1380, 1120,
1105, 1020, 830, 755cm -1 δ ccl4 1.31 (S, 6H), 2.81 (S, 2H), 7.18 (d
,
4H) Elemental analysis C H S Cl Calculated value % 60.17 6.01 16.06 17.76 Measured value % 59.06 6.07 16.55 17.56 (3) Synthesis of 2-(4-chlorophenyl)-2-methylpropylthiol 0.095 g of lithium aluminum hydride in 25 ml of dry ether and bis-[2-(4-chlorophenyl) dissolved in 10 ml of ether.
-2-Methylpropyl disulfide 1.0g
was added dropwise, and the mixture was reacted under reflux for 2 hours. After the reaction is complete, the reaction product is drained into water, 15% dilute sulfuric acid is added,
Extracted with benzene. The benzene layer was washed with saturated brine, dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.0 g of a liquid residue. ν film nax 2965, 2570, 1495, 1405, 1390, 1370,
1105, 1020, 830cm -1 δ ccl4 0.80 (t, 1H), 1.33 (S, 6H), 2.68 (d
,
2H), 7.23 (S, 4H) 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. Insecticide of the present invention. The first feature of the acaricidal composition 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 agricultural, horticultural, and forest pests that cause damage to paddy rice, field crops, cotton, fruit trees, forests, etc. (e.g., leafhoppers, planthoppers, beetles, rice beetles, rice weevils, rice weevils, stink bugs, aphids, Not only green caterpillars, armyworms, mealybugs, mealybugs, seed flies, sink beetles, scale insects, leafhoppers, spider mites, American white beetles, gypsy moths, bark beetles, nematodes, thrips, etc.), but also storage pests such as weevils, cutworms, and flies. It has a control effect at low concentrations against a wide range of pests, including sanitary pests such as mosquitoes, cockroaches, etc. The second feature of the composition of the present invention is that it is an organophosphorus insecticide. Acaricides and/or carbamate insecticides. Effective against insects that have already developed resistance to acaricides. It has an acaricidal effect and is also difficult to develop drug resistance against various insect pests. Furthermore, the third feature is that the composition of the present invention is compatible with general organophosphorus insecticides. Acaricides and carbamate insecticides. It has fast-acting properties not found in acaricides, and can make pests fall and turn over in a short time after being sprayed. Furthermore, the fourth feature is that it has many excellent features such as low toxicity to fish and warm-blooded animals and no risk of causing environmental pollution, making it an extremely ideal insecticide. It can be said to be an acaricide. When actually applying the composition of the present invention, it is sufficiently effective even if the composition itself is diluted, but in order to make it easier to use as a pesticidal agent, various carriers are mixed into the formulation. It is generally applied after diluting it depending on the situation. The formulation of the composition of the present invention does not require any special conditions, and can be prepared in accordance with general agricultural chemicals and epidemic prevention drugs.
Emulsions, wettable powders, powders, fine granules, granules, oils, aerosols,
It can be prepared in any form such as heating fumigants (mosquito coils, electric mosquito repellents, etc.), fogging agents such as fogging, non-heating fumigants, poison baits, etc., and 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, phenyl α
A composition with stable effects can also be obtained by adding an appropriate amount of arylamines or benzophenone compounds such as -naphthylamine, phenyl β-naphthylamine, and a condensate of penetidine and acetone as a stabilizer. Further, 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. Compound of general formula [] and pyrethroid insecticide in the composition of the present invention. Composition ratio with acaricide is 99:
The ratio is 1 to 1:99, preferably 10:1 to 1:1. When the composition of the present invention is formulated, the active ingredient concentration is 1 to 20% for emulsions, 0.3 to 3% for powders, 5 to 50% for wettable powders, 0.5 to 50% for granules, and 0.1 to 1% for aerosols. % (both weight %) is desirable. Next, some examples of formulations in which the composition of the present invention is used as an agricultural chemical or an epidemic prevention drug will be shown, but the present invention is not limited to these. All "parts" indicate "parts by weight.""Pyrethroid insecticide and acaricide" in the formulation example
represents the compound described in the present specification. Similarly, "compounds in Table 1" refer to any one of the compounds listed in Table 1.
Indicates the species. Formulation Example 1 5 parts of the compound shown in Table 1, pyrethroid insecticide. 5 parts of acaricide, 10 parts of emulsifier Solpol SM-200 (trade name of Toho Chemical), and 70 parts of xylene are stirred and mixed to form an emulsion. Formulation Example 2 1 part of the compound in Table 1, pyrethroid insecticide. Dissolve 1 part of acaricide in acetone and make powder clay 98
After adding 50% of the mixture, stir to evaporate the acetone and make a powder. Formulation Example 3 Add 5 parts of the compound shown in Table 1 to pyrethroid insecticide. Add 5 parts of acaricide and emulsifier Solpol 355TLL.
(Toho Chemical brand name) Add 5 parts, stir well,
Add 75 parts of diatomaceous earth (300 mesh) and thoroughly stir and mix in a Raikai machine to prepare a wettable powder. Formulation Example 4 Add pyrethroid insecticide to 3 parts of the compound in Table 1. Add 3 parts acaricide, 90 parts clay, toyolignin
Add 4 parts of CT (registered trade name of Toyobo), mix well, add water, stir and mix, granulate using a granulator, and dry to obtain granules. Formulation Example 5 One part of the compound in Table 1 plus pyrethroid insecticide. Add 1 part of acaricide, dissolve in white kerosene, etc., and make the whole 100%
It is treated as an oil agent. Formulation Example 6 Add pyrethroid insecticide to 0.2g of the compound in Table 1.
Add 0.2 g of acaricide, 0.9 g of synergist, and 0.3 g of BHT, dissolve in 20 ml of methanol, and make each carrier for mosquito coil (a mixture of tab powder, lees powder, and wood flour in the ratio of 3:5:1). After uniformly stirring and mixing with 99.4g and evaporating the methanol, add 150ml of water, mix thoroughly, and mold and dry to make a mosquito coil. Formulation Example 7 0.1g of the compound shown in Table 1, pyrethroid insecticide.
Add 0.2g of BHT to 0.1g of acaricide, 1.0g of synergist,
Dissolve it in chloroform, adsorb it on a 0.3 cm thick paper, and heat it on an electric heating plate to prepare a fiber fumigation composition. Formulation Example 8 0.1 part of the compound shown in Table 1, pyrethroid insecticide.
Acaricide 0.1 part, synergist 0.3 part, xylol 7 parts,
Mix and dissolve 7.5 parts of deodorized kerosene. Fill the aerosol container with this and attach the valve. 80 parts of propellant (liquefied petroleum gas) is pressurized and filled through the valve part to form an aerosol. Formulation Example 9 0.1 part of the compound in Table 1, pyrethroid insecticide.
Acaricide 0.1 part, synergist 0.3 part, deodorized kerosene 11.5 parts,
Mix with 1 part of emulsifier Atmos 300 (registered trade name of Atlas Chemical Company), add 50 parts of pure water and emulsify. This is filled into an aerosol container with 37 parts of a 3:1 mixture of butane bromide and deodorized propane to form a water-based aerosol. Next, the insecticide of the present invention. List the names of specific pests to which acaricides can be applied [scientific name - (Japanese name)]. 1 Hemiptera Nephotettix cincticeps Uhler Sogatella furcifera Horvath Nilaparvata lugens Sta゜l Laodelphax striatellus Falle′n Eurydema rugosum Motschulsky Eysarcoris parvus Uhler Halyomorphamista Uhler Lagynotomus elongatus Dallas Nezara viridula Linne′ Cletus trigonus Thunber′g Stephanitis nashi Esaki et Takeya Stephanitis pyrioides Scott Psylla pyrisuga Fo¨rster Psylla mali Schmidberger Aleurolobus taonabae Kuwana Dialeurodes citri Ashmead Trialeurodes vaporaiorum Westwood Aphis gossypii Glover Brevicoryne brassicae Linn′e Myzus pers icae Sulzer (Green peach aphid) Rhopalosiphum maidis Fitch (Millet aphid) Icerya purchasi Maskell (Icerya purchasi Maskell) Planococcus citri Risso (Orange mealybug) Unaspis yanonensis Kuwana (Yanone mealybug) 2 Lepidoptera (Lepidoptera) Canephora asiatica Staudinger (Minoga) Spulerina astaurcta Meyrick Phyllonorycter ringoneella Matsumura
(Plutella xylostella Linn′e) Promalactis inopisema Butler (Boll moth) Adoxophyes orana Fischer von
Ro¨slerstamm Bactra furfura′na Haworth Leguminivora glycinivorella Matsumura
Cnaphalocrocis medinalis Guen′ee Etiella zinckenella treitschke Ostrinia furnacalis Guen′ee Pleurophya derogata Fabricius 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 Linn′e Plusia nigrisigna Walker Spodoptera litura Fablicirs Parnara guttataBremer et Gray Pieris rapae crucivora Boisduval Chilo suppressalis Walker 3 Coleoptera Melanotus fortnumi Cande'ze Anthrenus verbasci Lunn'e Tenebroides mauritanicus Linn'e Lyctus brunneus Stephens bark beetle) Henosepilachna vigintioctopunctata
Fablicius Monochamus alternatus Hope Xylotrechus pyrrhoderus Bates Aulacophora femoralis Motschlusky Oulema oryzae Kuwayama Phyllotreta striolata Fablicus Callosobruchus chinensis Linn'e (Azuki bean weevil) Echinocnemis Squameus Billberg (Momochi Yotsukiri Muarushi) Anomala Cuprea Hope (Douganebui) Popillia Japonica Newman (Mamekogane) 4 Hymenoptera Athalia rosae japonensis Rohwer Arge similis Vollenhoven Arge pagana Panzer 5 Piptera Tipula aino Alexander Culex pipiens fatigans Wiedemann Aedes aegypti Linn'e (Netsu Taishimaka) Asphondylia SP. S CUCURBITAE COQUILLETTTTTT (Inecarabae) Agromyza ORYZAE MUNAKATA 6 Siphonaptera Pulex irritans Linn'e Xenopsylla cheopis Rothschild Ctenocephalides Canis Curtis 7 Thysanophera Scirtothrips dorsalis Hood Thrips tabaci Lindeman Thrips) Chloethrips oryzae Williams 8 Anoplura Pediculus humanus corporis De Geer Phthirus pubis Linn'e Haematopinus eurysternus Nitzsh 9 Psocoptera Trogium pulsatsrium Lunn'e Yatate beetle ) Liposcelis bostrychophilus Badonnel 10 Orthoptera Gryllotalpa africana palisot de Beauvois
Locusta migratoria danica Linn′e Oxya yezoensis Shiraki 11 Dictyoptera Blattella germanica Linn′e Periplaneta fuliginosa Serville 12 Acarina Boophilus microplus Canestrini Polyphagoharsonemus latus Banks Panonychus cutri McGregor Tetranychus cinnabarinus Boisduval Tetranychus urticae Koch Rhizoglyphus echinophus Fumouze et
Robin Next, the composition of the present invention kills insects. The action and effect as an acaricide will be explained in detail by giving test examples. Test example 1 Effect on German cockroaches.
A fixed concentration acetone solution of the compound shown in the table was added dropwise and air-dried to produce a dry film. On the other hand, the compounds shown in Table 1 and pyrethroid insecticides were treated in the same manner. A solution of a predetermined concentration of acetone mixed with an acaricide at a ratio of 1:1 was dropped and air-dried to form a dry film of the compound. Apply butter to the inner wall of a waist-high shear, release 10 female adult German cockroaches per shear, and calculate the mortality rate after 24 hours using each compound in Table 1 alone or with the same compound and pyrethroid insecticide. The LD-50 value when mixed with acaricide was determined. In the case of either compound, pyrethroid insecticidal effects were higher than in the case of single treatment. The efficacy was higher when acaricide was mixed, and the activity was more than doubled. Test Example 2 Effect on Spodoptera vulgaris A 3rd instar larva of Spodoptera vulgaris was placed in a polyethylene cup with a diameter of 10 cm, and the compounds shown in Table 1 were used alone or in combination with a pyrethroid insecticide. An emulsion containing acaricides mixed at a ratio of 1:1 was prepared according to Formulation Example 1, diluted with water to a predetermined concentration, and sprayed directly onto larvae using a spray tower at 2 ml per cup. Artificial feed was immediately given, and 24 hours later, the mortality rate of each insect was determined and the LC-50 value was calculated. Pyrethroids kill insects more effectively than each compound alone. When acaricides were mixed, an increase in efficacy of more than two times was observed in all combinations. Test Example 3 Effect on spider mites Adult two-spotted spider mites were released onto a 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.The results are shown in Table 1. LC-50 value and pyrethroid insecticidal effect of compound alone. When acaricides are added
The LC-50 value of the latter was less than 1/2, indicating a high synergistic effect. Test Example 4 Effects on sensitive brown planthopper Young paddy rice seedlings (2-3 true leaves) were grown hydroponically in pots with a diameter of 5 cm. The chemical solutions were treated using a sprayer at 3 ml/pot. After air-drying, the seedlings were covered with a wire mesh cylinder, and 10 male adults of the susceptible brown planthopper (from Chigasaki) were added to each pot.
The heads were released and left in a room at 25°C. 24 hours after treatment,
The number of live and dead insects was investigated and the mortality rate was calculated. The results are shown in Table 2 as the average value of three runs.
【表】
リン
各供試化合物(第1表の化合物番号で示す)と
ピレスロイド系殺虫.殺ダニ剤とを混合すること
により100%の死虫率を示し、すぐれた相乗効果
が認められた。
試験例 5
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Vol.4No.6、119ページ
(1938)〕によりイエバエ成虫(雄)20頭を使用し
て、製剤例5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の他のピレスロイド系
殺虫.殺ダニ剤を混合した油剤の所定濃度の液に
白灯油で希釈し、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(分)(以下
K T50値と略す。)を求め比較した。その結果
を第3表に示す。[Table] Phosphorus Each test compound (indicated by compound number in Table 1) and pyrethroid insecticide. When mixed with acaricides, a 100% insect mortality rate was achieved, demonstrating an excellent synergistic effect. Test Example 5 Table 1 was prepared according to Formulation Example 5 using 20 adult house flies (male) using Campbell's turntable method [Soap and Sanitary Chemicals Vol. 4 No. 6, page 119 (1938)]. An oil agent containing only the compound shown in 2. and other pyrethroid insecticides using this compound. Spray 1 ml of each oil solution mixed with acaricide at a specified concentration diluted with white kerosene, and calculate the time (minutes) for half of the house flies tested to fall and roll over (hereinafter abbreviated as K T 50 value). I found it and compared it. The results are shown in Table 3.
【表】
その結果、第1表の化合物、ピレスロイド系殺
虫.殺ダニ剤単独の時よりも、両者を混合するこ
とにより殺虫速度が速くなり相乗効果が認められ
た。試験例1.2.3.4.5と同様の方法で、本明細書記
載のフエンバレレート、パーメスリン、アレスリ
ン、ネオピナミン、カデスリン以外のピレスロイ
ド系殺虫.殺ダニ剤と前記第1表記載の化合物と
の混合剤について試験した結果、試験例1.2.3.4.5
とほゞ同様の殺虫.殺ダニ剤効果が得られた。[Table] As a result, the compounds in Table 1 were found to be pyrethroid insecticides. By mixing the acaricides, the insecticidal rate was faster than when using only the acaricide alone, and a synergistic effect was observed. Using a method similar to Test Example 1.2.3.4.5, pyrethroid insecticides other than fenvalerate, permethrin, allethrin, neopinamine, and cadethrin described herein. As a result of testing a mixture of acaricide and the compound listed in Table 1 above, Test Example 1.2.3.4.5
Almost the same insecticide. Acaricide effect was 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[d−2−シス(ペン
タ−2′,4′−ジエニル)]−3−メチルシクロペン
タ−2−エン−4−オール−1−オニル d−ト
ランス−クリサンセメート(ピレトリン)、[d
−2−シス(ペンタ−2′,4′−ジエニル)]−3−
メチルシクロペンタ−2−エン−4−オール−1
−オニル d−トランス−ピレスート(ピレトリ
ン)、[d−2−シス−(ブタ−2′−エニル)]−
3−メチルシクロペンタ−2−エン−4−オール
−1−オニル d−トランス−クリサンセメート
(シネリン)、[d−2−シス(ブタ−2′−エニ
ル)]−3−メチルシクロペンタ−2−エン−4−
オール−1−オニル d−トランスピレスレート
(シネリン)、dl−2−アリル−3−メチルシク
ロペンタ−2−エン−4−オール−1−オニル
dl−シス,トランス−クリサンセメート、dl−2
−(α−フルフリル)−3−メチルペンタ−2−エ
ン−4−オール−1−オニル dl−シス,トラン
ス−クリサンセメート、6−クロロピペロニル
dl−シス,トランス−クリサンセメート、2,4
−ジメチルベンジル dl−シス,トランス−クリ
サンセメート、N−(3,4,5,6−テトラハ
イドロフタルイミド)メチル dl−シス、トラン
ス−クリサンセメート、4−アリルベンジル dl
−シス、トランス−クリサンセメート、2,6−
ジメチル−4−アリルベンジル dl−シス,トラ
ンス−クリサンセメート、5−ベンジル−3−フ
ルフリル dl−シス,トランス−クリサンセメー
ト、5−プロパギル−2−フルフリル dl−シ
ス,トランス−クリサンセメート、5−ベンジル
−3−フルフリルメチル d−シス(1R,3S,
E)2,2−ジメチル−3−(2−オキソ−2,
2,4,5−テトラヒドロチオフエニリデンメチ
ル)シクロプロパンカルボキシレート、dl−2−
アリル−3−メチル−シクロペンタ−2−エン−
4−オール−1−オニル 2,2,3,3−テト
ラメチル−シクロプロパンカルボキシレート、3
−フエノキシベンジル クリサンセメート、α−
シアノ−3−フエノキシベンジル クリサンセメ
ート、α−シアノ−3−フエノキシベンジル
2,2,3,3−テトラメチルシクロプロパンカ
ルボキシレート、3−フエノキシベンジル 2,
2−ジメチル−3−(2,2−ジクロロビニル)
シクロプロパンカルボキシレート、α−シアノ−
3−フエノキシベンジル 2,2−ジメチル−3
−(2,2−ジクロロビニル)シクロプロパンカ
ルボキシレート、α−シアノ−3−フエノキシベ
ンジル 2,2−ジメチル−3−(2,2−ジブ
ロモビニル)シクロプロパンカルボキシレート、
α−シアノ−3−フエノキシベンジル 2−(p
−クロロフエニル)−3−メチルブチレート、α
−シアノ−3−フエノキシベンジル 2−(2−
クロロ−4−トリフルオロメチルフエニルアミ
ノ)−3−メチルブチレートからなるピレスロイ
ド系殺虫、殺ダニ剤のうちの1種または2種以上
を含有してなる殺虫、殺ダニ用組成物。[Claims] 1 [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 methylenedioxy, R 1 is a methyl group or ethyl group, R 2 is a methyl, ethyl group or isopropyl group, R 3 is a phenyl group substituted with a lower alkyl group or a lower alkoxy group, or a phenyl group substituted with methylenedioxy. hydrogen atom or 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-
One or more arylethyl ether or thioether derivatives and [d-2-cis(penta-2',4'-dienyl)]-3-methylcyclopent-2-en-4-ol-1-onyl d-trans-chrysansemate (pyrethrin), [d
-2-cis(penta-2',4'-dienyl)]-3-
Methylcyclopent-2-en-4-ol-1
-onyl d-trans-pyresuth (pyrethrin), [d-2-cis-(but-2'-enyl)]-
3-Methylcyclopent-2-en-4-ol-1-onyl d-trans-chrysansemate (cinerine), [d-2-cis(but-2'-enyl)]-3-methylcyclopenta- 2-en-4-
All-1-onyl d-transpyrethlate (cinerine), dl-2-allyl-3-methylcyclopent-2-en-4-ol-1-onyl
dl-cis, trans-chrysansemate, dl-2
-(α-furfuryl)-3-methylpent-2-en-4-ol-1-onyl dl-cis,trans-chrysanthemate, 6-chloropiperonyl
dl-cis,trans-chrysanthemate, 2,4
-dimethylbenzyl dl-cis, trans-chrysansemate, N-(3,4,5,6-tetrahydrophthalimido)methyl dl-cis, trans-chrysansemate, 4-allylbenzyl dl
-cis, trans-chrysansemate, 2,6-
Dimethyl-4-allylbenzyl dl-cis, trans-chrysanthemate, 5-benzyl-3-furfuryl dl-cis, trans-chrysanthemate, 5-propargyl-2-furfuryl dl-cis, trans-chrysanthemate, 5-benzyl-3-furfurylmethyl d-cis (1R, 3S,
E) 2,2-dimethyl-3-(2-oxo-2,
2,4,5-tetrahydrothiophenylidenemethyl)cyclopropanecarboxylate, dl-2-
Allyl-3-methyl-cyclopent-2-ene-
4-ol-1-onyl 2,2,3,3-tetramethyl-cyclopropanecarboxylate, 3
-Phenoxybenzyl chrysansemate, α-
Cyano-3-phenoxybenzyl chrysansemate, α-cyano-3-phenoxybenzyl
2,2,3,3-tetramethylcyclopropanecarboxylate, 3-phenoxybenzyl 2,
2-dimethyl-3-(2,2-dichlorovinyl)
Cyclopropane carboxylate, α-cyano-
3-phenoxybenzyl 2,2-dimethyl-3
-(2,2-dichlorovinyl)cyclopropanecarboxylate, α-cyano-3-phenoxybenzyl 2,2-dimethyl-3-(2,2-dibromovinyl)cyclopropanecarboxylate,
α-cyano-3-phenoxybenzyl 2-(p
-chlorophenyl)-3-methylbutyrate, α
-cyano-3-phenoxybenzyl 2-(2-
An insecticidal or acaricidal composition containing one or more of pyrethroid insecticides and acaricides consisting of chloro-4-trifluoromethylphenylamino)-3-methylbutyrate.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56160147A JPS5862104A (en) | 1981-10-09 | 1981-10-09 | Insecticidal and acaricidal composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP56160147A JPS5862104A (en) | 1981-10-09 | 1981-10-09 | Insecticidal and acaricidal composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5862104A JPS5862104A (en) | 1983-04-13 |
JPH0231685B2 true JPH0231685B2 (en) | 1990-07-16 |
Family
ID=15708879
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP56160147A Granted JPS5862104A (en) | 1981-10-09 | 1981-10-09 | Insecticidal and acaricidal composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5862104A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003015522A1 (en) * | 2001-08-16 | 2003-02-27 | Hoi-Seon Lee | Plant oil and chemical compound having acaricidal activity |
-
1981
- 1981-10-09 JP JP56160147A patent/JPS5862104A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS5862104A (en) | 1983-04-13 |
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