JPH0215545B2 - - Google Patents
Info
- Publication number
- JPH0215545B2 JPH0215545B2 JP5036380A JP5036380A JPH0215545B2 JP H0215545 B2 JPH0215545 B2 JP H0215545B2 JP 5036380 A JP5036380 A JP 5036380A JP 5036380 A JP5036380 A JP 5036380A JP H0215545 B2 JPH0215545 B2 JP H0215545B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- atom
- oxygen
- sulfur
- oxygen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 22
- 125000004434 sulfur atom Chemical group 0.000 claims description 18
- -1 methyl monosubstituted phenyl group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 239000000642 acaricide Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 230000006315 carbonylation Effects 0.000 claims description 5
- 238000005810 carbonylation reaction Methods 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical class O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 230000000895 acaricidal effect Effects 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241000238876 Acari Species 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002506 adulticidal effect Effects 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003905 agrochemical Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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 1
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-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
- XFTDRCCWEUCHSI-XSDATEAUSA-N (4s,5s)-4-methyl-5-(4-methylphenyl)-n-(oxan-2-yl)-2-sulfanylidene-1,3-oxazolidine-3-carboxamide Chemical compound O([C@H]([C@@H]1C)C=2C=CC(C)=CC=2)C(=S)N1C(=O)NC1CCCCO1 XFTDRCCWEUCHSI-XSDATEAUSA-N 0.000 description 1
- SPJLQKZVWZEOOR-UHFFFAOYSA-N 1-chloro-4-(4-nitrophenoxy)-2-propylsulfanylbenzene Chemical compound C1=C(Cl)C(SCCC)=CC(OC=2C=CC(=CC=2)[N+]([O-])=O)=C1 SPJLQKZVWZEOOR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QECPWYSZWLPANX-UHFFFAOYSA-N 2,2-dichloro-1-(4-ethoxyphenyl)-3-[(3-phenoxyphenyl)methyl]cyclopropane-1-carboxylic acid Chemical compound C1=CC(OCC)=CC=C1C1(C(O)=O)C(Cl)(Cl)C1CC1=CC=CC(OC=2C=CC=CC=2)=C1 QECPWYSZWLPANX-UHFFFAOYSA-N 0.000 description 1
- VXVWIRKAABQIGS-UHFFFAOYSA-N 2-isocyanatooxane Chemical compound O=C=NC1CCCCO1 VXVWIRKAABQIGS-UHFFFAOYSA-N 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- URYAFVKLYSEINW-UHFFFAOYSA-N Chlorfenethol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1=CC=C(Cl)C=C1 URYAFVKLYSEINW-UHFFFAOYSA-N 0.000 description 1
- RZXLPPRPEOUENN-UHFFFAOYSA-N Chlorfenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=C(Cl)C=C1 RZXLPPRPEOUENN-UHFFFAOYSA-N 0.000 description 1
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- AIKKULXCBHRFOS-UHFFFAOYSA-N Formothion Chemical compound COP(=S)(OC)SCC(=O)N(C)C=O AIKKULXCBHRFOS-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000819999 Nymphes Species 0.000 description 1
- JAYZFNIOOYPIAH-UHFFFAOYSA-N Oxydeprofos Chemical compound CCS(=O)CC(C)SP(=O)(OC)OC JAYZFNIOOYPIAH-UHFFFAOYSA-N 0.000 description 1
- 239000005921 Phosmet Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- PNAAEIYEUKNTMO-UHFFFAOYSA-N S-Seven Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C(Cl)C=C1Cl PNAAEIYEUKNTMO-UHFFFAOYSA-N 0.000 description 1
- 101000984731 Salvia officinalis (+)-bornyl diphosphate synthase, chloroplastic Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QUWSDLYBOVGOCW-UHFFFAOYSA-N Tetrasul Chemical compound C1=CC(Cl)=CC=C1SC1=CC(Cl)=C(Cl)C=C1Cl QUWSDLYBOVGOCW-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 description 1
- CGTWCAVZZBLHQH-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1C1(C(=O)OC(C#N)C=2C=C(OC=3C=CC=CC=3)C=CC=2)C(Cl)(Cl)C1 CGTWCAVZZBLHQH-UHFFFAOYSA-N 0.000 description 1
- QNZPBCQIYMPYAE-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 2-[2-chloro-4-(trichloromethyl)anilino]-3-methylbutanoate Chemical compound C=1C=CC(OC=2C=CC=CC=2)=CC=1C(C#N)OC(=O)C(C(C)C)NC1=CC=C(C(Cl)(Cl)Cl)C=C1Cl QNZPBCQIYMPYAE-UHFFFAOYSA-N 0.000 description 1
- YBUVYVPVPZIQAD-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 3-methyl-2-[4-(trichloromethoxy)phenyl]butanoate Chemical compound C=1C=C(OC(Cl)(Cl)Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 YBUVYVPVPZIQAD-UHFFFAOYSA-N 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- QDRXWCAVUNHOGA-UHFFFAOYSA-N acequinocyl Chemical compound C1=CC=C2C(=O)C(CCCCCCCCCCCC)=C(OC(C)=O)C(=O)C2=C1 QDRXWCAVUNHOGA-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229960002587 amitraz Drugs 0.000 description 1
- QXAITBQSYVNQDR-ZIOPAAQOSA-N amitraz Chemical compound C=1C=C(C)C=C(C)C=1/N=C/N(C)\C=N\C1=CC=C(C)C=C1C QXAITBQSYVNQDR-ZIOPAAQOSA-N 0.000 description 1
- 229910052586 apatite Inorganic materials 0.000 description 1
- BKAYSPSVVJBHHK-UHFFFAOYSA-N bis(4-chlorophenyl)-cyclopropylmethanol Chemical compound C=1C=C(Cl)C=CC=1C(C=1C=CC(Cl)=CC=1)(O)C1CC1 BKAYSPSVVJBHHK-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- AXGUBXVWZBFQGA-UHFFFAOYSA-N chloropropylate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OC(C)C)C1=CC=C(Cl)C=C1 AXGUBXVWZBFQGA-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- 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 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RIZMRRKBZQXFOY-UHFFFAOYSA-N ethion Chemical compound CCOP(=S)(OCC)SCSP(=S)(OCC)OCC RIZMRRKBZQXFOY-UHFFFAOYSA-N 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- GNDPAVKYAUIVEB-NTEUORMPSA-N furonazide Chemical compound C=1C=COC=1C(/C)=N/NC(=O)C1=CC=NC=C1 GNDPAVKYAUIVEB-NTEUORMPSA-N 0.000 description 1
- 229950001880 furonazide Drugs 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000021331 green beans Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- 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 1
- 239000003208 petroleum Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229950005488 proclonol Drugs 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 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
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- GIZSHQYTTBQKOQ-UHFFFAOYSA-N threo-Syringoylglycerol Chemical compound COC1=CC(C(O)C(O)CO)=CC(OC)=C1O GIZSHQYTTBQKOQ-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は新規な化合物、製造法及びその使用に
関し、詳しくは一般式（）
（式中、Ｙ，Ｚは酸素原子、又は硫黄原子を、
R1は低級アルキル基を、R2は異項原子として１
個の酸素原子又は硫黄原子を有する五員複素環又
はフエニル基又はモノもしくはジC1〜12アルキル
基、ハロゲン原子、ハロアルキル基、アルコキシ
基、もしくはメチレンジオキシ基置換フエニル基
を、R3は置換基を有しもしくは有せざるC5〜7の
シクロアルキル基、シクロアルケニル基、又は酸
素原子、硫黄原子、窒素原子の少くとも１種を有
する複素環を示す。但し、R1がメチル基を、R2
がメチル基モノ置換フエニル基を、Ｙ及びＺが
夫々酸素原子を示すとき、R3はシクロヘキシル
基ではない。）で表わされる化合物のトランス体、
その製造方法及び該化合物類を有効成分として含
有する殺ダニ剤に関するものである。
ダニ類の防除には、有機リン系化合物、ジニト
ロ系化合物等をはじめ、各種の化合物が使用され
ているが、近年、これらの薬剤に対し抵抗性を有
するダニ類が出現し、新しいタイプの殺ダニ剤が
望まれている。本発明者らは、従来の殺ダニ剤と
は異なる系統の化合物の中から、有効かつ経済的
な、安全性の高い殺ダニ剤を提供することを目的
として研究を重ね、前記一般式（）で表わされ
る化合物類が優れた殺ダニ活性を有することを見
い出し、本発明を完成した。
本発明化合物はナミハダニ、ミカンハダニ等の
各種の植物寄生性ハダニ類に有効であり、特に、
各種ダニの卵及び幼若虫のステージにおいては優
れた殺卵力、殺幼虫力、殺若虫力を示す。また、
温血動物に対する毒性は低く、安全性の高い薬剤
である。
一般式（）で示される本発明化合物のうち、
フエニル基の置換基として４−メチル基を有する
化合物が、特に優れた殺ダニ活性を有する。又
R2がチエニル基である化合物には、優れた草活
性を有するものである。
本発明化合物の製造方法としては、
(1) 一般式（）
（式中、R1，R2、Ｙは前記と同一の意味を示
す。）で表わされる化合物と一般式（）
R3NCZ （）
（式中R3及びＺは前記と同一）で表わされる
イソ（チオ）シアン酸類とを反応させる方法。
(2) 一般式（）
（式中、R1，R2，R3、Ｚは前記と同一）で表
わされる化合物と（チオ）カルボニル化試薬とを
反応させる方法等がある。
Ｙが酸素原子である化合物は(1)の製造方法によ
り好収率で製造できるが、Ｙが硫黄原子である化
合物は(2)の方法による方が好ましい。
(1)の製造方法を実施するには、一般式（）で
表わされる化合物を有機溶媒に溶解し、触媒とし
て、DBU（１，８−ジアザビシクロ（５，４，
０）ウンデセン−７）、水素化ナトリウム又は三
級アミン類を用いて、一般式（）で表わされる
化合物と反応させる。
有機溶媒としては、トルエン、テトラヒドロフ
ラン、ジメチルスルホキシド等の一般の不活性溶
媒が用いられるが、脱水して用いるのが望まし
い。
反応は、０℃〜室温で１〜数時間、撹拌下行
う。反応終了後、反応液を水にあけ、析出する結
晶を濾取するか又は有棋溶媒で抽出する等の通常
の後処理を行うことにより目的物を得る。
前記一般式（）で表わされる化合物は例えば
下記反応式に示す方法により製造できる。
本発明化合物は立体異性体を有するが、殺ダニ
剤として有効な化合物はトランス体である。製造
工程にあつては、(イ)法では化合物（）、(ロ)法で
は化合物（）において、比較的容易にスレオ体
だけを分離することができる。また、エリスロ体
からスレオ体への異性化も可能である。
(2)の製造方法を実施するには一般式（）で表
わされる化合物を、有機溶媒中、酸結合剤の存在
下、（チオ）カルボニル化試薬と反応させる。
（チオ）カルボニル化試薬としては炭酸カリ、
（チオ）ホスゲン、トリクロロメチルクロロホル
メート等の一般の（チオ）カルボニル化試薬が用
いられる。有機溶媒としては酢酸エチル、ベンゼ
ン、クロロホルム等の一般の不活性溶媒が使用で
き、酸結合剤としてはジメチルアニリン、トリエ
チルアミン等のアミン類をはじめ一般の塩基が使
用できる。反応は、０℃〜室温で１〜数時間行
う。反応後、塩酸水溶液、水等で塩基を除去し、
脱水して溶媒を留去する等の一般的後処理を行つ
て目的物を得る。
前記一般式（）で表わされる化合物は新規化
合物であり、例えば、前記一般式（）で表わさ
れる化合物と一般式（）で表わされる化合物と
を反応させることにより製造できる。
本発明化合物は、下記構造式に＊印で示した不
斉炭素による異性体のうち、対掌体を含むトラン
ス体であるが、本発明化合物のうち、R3が置換
シクロヘキシル、テトラヒドロピラニル等の飽和
複素環である時はカルバモイル基部分にも異性体
を含む。それらの異性体はいずれも殺ダニ活性を
有しており、トランス体、シス体、ジアステレオ
マー混合物、いずれも本発明に含まれるものであ
る。
第１表に本発明化合物の具体例を示す。
The present invention relates to a novel compound, a method for producing it, and its use, in particular, the general formula () (In the formula, Y and Z are oxygen atoms or sulfur atoms,
R 1 is a lower alkyl group, R 2 is 1 as a foreign atom
R 3 is a substituted phenyl group, a 5-membered heterocycle having 5 oxygen atoms or sulfur atoms, or a mono- or di-C 1-12 alkyl group, a halogen atom, a haloalkyl group, an alkoxy group, or a methylenedioxy group; It represents a C5-7 cycloalkyl group, a cycloalkenyl group, with or without a group, or a heterocycle having at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. However, R 1 is a methyl group, R 2
When represents a phenyl group monosubstituted with a methyl group, and Y and Z each represent an oxygen atom, R 3 is not a cyclohexyl group. ) trans isomer of the compound represented by
The present invention relates to a method for producing the same and an acaricide containing the compound as an active ingredient. Various compounds are used to control mites, including organophosphorus compounds and dinitro compounds, but in recent years, mites that are resistant to these chemicals have appeared, and new types of mites are being used. A tick agent is desired. The present inventors have conducted extensive research with the aim of providing an effective, economical, and highly safe acaricide from among compounds of a different type from conventional acaricides, and have developed the general formula () The present invention was completed based on the discovery that compounds represented by the following have excellent acaricidal activity. The compounds of the present invention are effective against various plant-parasitic spider mites, such as the two-spotted spider mite and the orange spider mite.
It exhibits excellent ovicidal, larvicidal, and nymphicidal powers on the egg and nymph stages of various mites. Also,
It is a highly safe drug with low toxicity to warm-blooded animals. Among the compounds of the present invention represented by the general formula (),
A compound having a 4-methyl group as a substituent of a phenyl group has particularly excellent acaricidal activity. or
Compounds in which R 2 is a thienyl group have excellent herbal activity. As a method for producing the compound of the present invention, (1) General formula () (In the formula, R 1 , R 2 and Y have the same meanings as above.) Compounds represented by the general formula () R 3 NCZ () (In the formula, R 3 and Z have the same meanings as above) A method of reacting with iso(thio)cyanic acids. (2) General formula () There is a method of reacting a compound represented by the formula (wherein R 1 , R 2 , R 3 and Z are the same as above) with a (thio)carbonylation reagent. Compounds in which Y is an oxygen atom can be produced with good yield by the production method (1), but compounds in which Y is a sulfur atom are preferably produced by the method (2). To carry out the production method (1), the compound represented by the general formula () is dissolved in an organic solvent, and DBU (1,8-diazabicyclo(5,4,
0) Undecene-7), sodium hydride or tertiary amines are used to react with the compound represented by the general formula (). As the organic solvent, general inert solvents such as toluene, tetrahydrofuran, and dimethyl sulfoxide are used, but it is preferable to use them after dehydration. The reaction is carried out at 0° C. to room temperature for 1 to several hours with stirring. After the reaction is completed, the desired product is obtained by pouring the reaction solution into water and performing usual post-treatments such as filtering the precipitated crystals or extracting them with an alimentary solvent. The compound represented by the general formula () can be produced, for example, by the method shown in the reaction formula below. Although the compound of the present invention has stereoisomers, the compound effective as an acaricide is the trans isomer. In the manufacturing process, only the threo isomer can be relatively easily separated from compound () in method (a) and compound () in method (b). Furthermore, isomerization from erythro form to threo form is also possible. To carry out the production method (2), a compound represented by the general formula () is reacted with a (thio)carbonylation reagent in an organic solvent in the presence of an acid binder. As a (thio)carbonylation reagent, potassium carbonate,
Common (thio)carbonylation reagents such as (thio)phosgene and trichloromethyl chloroformate are used. As the organic solvent, common inert solvents such as ethyl acetate, benzene, and chloroform can be used, and as the acid binder, common bases including amines such as dimethylaniline and triethylamine can be used. The reaction is carried out at 0°C to room temperature for 1 to several hours. After the reaction, remove the base with an aqueous hydrochloric acid solution, water, etc.
The desired product is obtained by performing general post-treatments such as dehydration and distilling off the solvent. The compound represented by the general formula () is a new compound, and can be produced, for example, by reacting the compound represented by the general formula () with the compound represented by the general formula (). The compound of the present invention is a trans isomer including the enantiomer among the isomers due to the asymmetric carbon indicated by an asterisk in the structural formula below, but among the compounds of the present invention, R 3 is substituted with cyclohexyl, tetrahydropyranyl, etc. When it is a saturated heterocycle, the carbamoyl group also includes isomers. All of these isomers have acaricidal activity, and all of the trans isomers, cis isomers, and diastereomer mixtures are included in the present invention. Table 1 shows specific examples of the compounds of the present invention.
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】【table】
【表】
以下に本発明の製造法の実施例を挙げる
実施例 １
トランス−４−メチル−５−（４−メチルフエ
ニル）−３−（２−テトラヒドロピラニルカルバ
モイル）−２−オキサゾリドン：
トランス−４−メチル−５−（４−メチルフエ
ニル）−２−オキサゾリドン1.5ｇをジメチルスル
ホキシド20mlに溶解し、氷冷下２−テトラヒドロ
ピラニルイソシアナート0.9ｇ及びDBU（１，８
−ジアザビシクロ−（５，４，０）−ウンデセン−
７）１滴を加えた後、１時間室温にて撹拌を続け
た。反応終了後、反応液を水にあけ、酢酸エチル
で抽出し、水洗、硫酸マグネシウム乾燥後、溶媒
を留去して得られたオイル状物質をカラムクロマ
トグラフイーにより分離精製して目的物0.7ｇを
得た。
mp 94.5〜96℃
Rf 0.33／（酢酸エチル／ベンゼン＝１／19）
実施例 ２
トランス−４−メチル−５−（４−メチルフエ
ニル）−３−（２−テトラヒドロピラニルカルバ
モイル）−オキサゾリジン−２−チオン：
１−（２−テトラヒドロピラニル）−３−〔スレ
オ−１−ヒドロキシ−１−（４−メチルフエニル）
−２−プロピル〕ウレア1.2ｇとＮ，Ｎ−ジメチ
ルアニリン1.0ｇとを酢酸エチル10mlに溶解し、
撹拌下０℃でチオホスゲン0.7ｇと酢酸エチル５
mlの混合溶液を滴下した。その後０℃で３時間反
応を続け、反応終了後、反応溶液を５％塩酸水溶
液にあけ、酢酸エチル抽出し、水洗、硫酸マグネ
シウム乾燥後、溶媒を留去して得られたオイル状
物質をカラムクロマトグラフイーにより分離精製
して目的物0.5ｇを得た。
nD 20.5：1.5800
Rf：0.5／（酢酸エチル／ヘキサン＝１）
本発明の殺ダニ剤は、前記一般式（）で表わ
される化合物の１種又は２種以上を有効成分とし
て含有するものであり、有効成分化合物の純品の
ままでも使用できるが、通常、一般の農薬のとり
得る形態、即ち、水和剤、粒剤、粉剤、乳剤、フ
ロアブル等の形態で使用される。添加剤及び担体
としては、固形剤を目的とする場合は、大豆粉、
小麦粉等の植物性粉末、珪藻土、燐灰石、石膏、
タルク、パイロフイライト、クレイ等の鉱物性微
粉末が使用される。
液体の剤型を目的とする場合はケロシン、鉱
油、石油、ソルベントナフサ、キシレン、シクロ
ヘキサン、シクロヘキサノン、ジメチルホルムア
ミド、ジメチルスルホキシド、アルコール、アセ
トン、水等を溶剤として使用する。これらの製剤
において、均一なかつ安定な形態をとるために必
要ならば界面活性剤を添加することもできる。こ
のようにして得られた水和剤、乳剤、フロアブル
等は、水で所定の濃度に希釈して懸濁液あるいは
乳濁液として、粉剤、粒剤はそのまま、植物に散
布する方法で使用される。
次に製剤の実施例を示すが、添加する担体、界
面活性剤等はこれらの実施例に限定されるもので
はない。
実施例３ 乳剤
本発明化合物 10部
アルキルフエニルポリオキシエチレン ５〃
ジメチルホルムアミド 50〃
キシレン 35〃
以上を混合溶解し、使用に際し水で希釈して乳
濁液として散布する。
実施例４ 水和剤
本発明化合物 20部
高級アルコール硫酸エステル ５〃
珪藻土 70〃
ホワイトカーボン ５〃
以上を混合して微粉に粉砕し、使用に際し水で
希釈して懸濁液として散布する。
実施例５ 粉剤
本発明化合物 ５部
タルク 94.6〃
シリカ 0.3〃
アルキルフエニルポリオキシエチレン 0.1〃
以上を混合粉砕し、使用に際してはそのまま散
布する。
なお、本発明化合物は単独でも十分有効である
ことはいうまでもないが、殺成虫力が弱いため、
植物寄生性ハダニに対し殺成虫力を持つ化合物の
１種又は２種以上と混用すると極めて有用であ
る。本発明化合物は殺成虫力を持つ化合物以外に
も各種の農薬の１種は２種以上と混合して使用す
ることも出来る。
本発明化合物と混用して使用できる殺ダニ剤や
殺虫剤の代表例を以下に示す。
殺ダニ剤（殺菌剤）：BCPE、クロルベンジレー
ト、クロルプロピレート、プロクロノール、フ
エニソブロモレート、ケルセン、ジノブトン、
ビナパクリル、クロルフエナミジン、アミトラ
ズ、BPPS、PPPS、ベンゾメート、シヘキサ
チン、ジスタノキサン、ポリナクチン、キノメ
チオネート、チオキノツクス、CPCBS、テト
ラジホン、テトラスル、シクロプレート、カヤ
サイド、カヤホープ、３−ｎ−ドデシル−１，
４−ナフトキノン−２−イルアセテート、多硫
化石灰、
有機燐系殺虫剤（殺ダニ剤）：フエンチオン、フ
エニトロチオン、ダイアジノン、クロルピリホ
ス、ESP、バミドチオン、フエントエート、ジ
メトエート、ホルモチオン、マラソン、ジプテ
レツクス、チオメトン、ホスメツト、メナゾ
ン、ジクロルボス、アセフエート、EPBP、ジ
アリホール、メチルパラチオン、オキシジメト
ンメチル、エチオン、アルデイカープ、プロポ
キシユール、
ピレスロイド系殺虫剤（殺ダニ剤）：パーメスリ
ン、サイパーメスリン、デカメスリン、フエン
バレレイト、フエンプロパスリン、ピレトリ
ン、アレスリン、テトラメスリン、レスメスリ
ン、パルスリン、ジメスリン、プロパスリン、
プロスリン、
３−フエノキシベンジル−２，２−ジクロロ
−１−（４−エトキシフエニル）−１−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
−ジクロロ−１−（４−エトキシフエニル）−１
−シクロプロパンカルボキシレート、
（RS）−α−シアノ−３−フエノキシベンジ
ル（RS）−２−（４−トリクロロメトキシフエ
ニル）−３−メチルブチレート、
（RS）−α−シアノ−３−フエノキシベンジ
ル（RS）−２−（２−クロロ−４−トリクロロ
メチルアニリノ）−３−メチルブチレート
機械油。
次に試験例を挙げ本発明化合物の殺ダニ活性を
示す。
試験例１ ナミハダニに対する効力
２寸鉢に播種したインゲンの発芽後７〜10日を
経過した第１本葉上に、有機燐剤抵抗性のナミハ
ダニの雌成虫を30頭接種したのち、前記薬剤の実
施例３に示された乳剤の処方に従がい、化合物濃
度が500、125ppmになるように水で希釈して散布
した。散布３日後に殺虫率を求めるとともに、成
虫を除去し、この３日間に産付された卵に関し、
成虫まで発育し得たか否かを11日目に調査し、殺
ダニ有効度を求めた。結果は次の通りである。[Table] Examples of the production method of the present invention are listed below. Example 1 Trans-4-methyl-5-(4-methylphenyl)-3-(2-tetrahydropyranylcarbamoyl)-2-oxazolidone: trans-4- 1.5 g of methyl-5-(4-methylphenyl)-2-oxazolidone was dissolved in 20 ml of dimethyl sulfoxide, and 0.9 g of 2-tetrahydropyranyl isocyanate and DBU (1,8
-Diazabicyclo-(5,4,0)-undecene-
7) After adding 1 drop, stirring was continued for 1 hour at room temperature. After the reaction was completed, the reaction solution was poured into water, extracted with ethyl acetate, washed with water, dried with magnesium sulfate, and the solvent was distilled off. The resulting oily substance was separated and purified by column chromatography to obtain 0.7 g of the desired product. I got it. mp 94.5-96℃ Rf 0.33/(ethyl acetate/benzene = 1/19) Example 2 trans-4-methyl-5-(4-methylphenyl)-3-(2-tetrahydropyranylcarbamoyl)-oxazolidine-2-thione : 1-(2-tetrahydropyranyl)-3-[threo-1-hydroxy-1-(4-methylphenyl)
1.2 g of -2-propyl]urea and 1.0 g of N,N-dimethylaniline were dissolved in 10 ml of ethyl acetate,
Thiophosgene 0.7 g and ethyl acetate 5 at 0°C under stirring
ml of the mixed solution was added dropwise. Thereafter, the reaction was continued for 3 hours at 0°C, and after the reaction was completed, the reaction solution was poured into a 5% aqueous hydrochloric acid solution, extracted with ethyl acetate, washed with water, dried with magnesium sulfate, and the solvent was distilled off. Separation and purification by chromatography yielded 0.5 g of the target product. n D 20.5 : 1.5800 Rf: 0.5/(ethyl acetate/hexane = 1) The acaricide of the present invention contains one or more compounds represented by the above general formula () as an active ingredient. Although the active ingredient compound can be used as a pure product, it is usually used in the form that common agricultural chemicals can take, that is, in the form of wettable powders, granules, powders, emulsions, flowables, etc. As additives and carriers, soybean flour,
Vegetable powders such as wheat flour, diatomaceous earth, apatite, gypsum,
Fine mineral powders such as talc, pyrofluorite, and clay are used. When a liquid dosage form is intended, kerosene, mineral oil, petroleum, solvent naphtha, xylene, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, water, etc. are used as the solvent. In these preparations, a surfactant may be added if necessary in order to obtain a uniform and stable form. The wettable powders, emulsions, flowables, etc. obtained in this way can be diluted with water to a predetermined concentration to form a suspension or emulsion, and the powders and granules can be used as they are by spraying them on plants. Ru. Next, examples of formulations will be shown, but the carriers, surfactants, etc. to be added are not limited to these examples. Example 3 Emulsion Compound of the present invention 10 parts Alkylphenylpolyoxyethylene 5 Dimethylformamide 50 Xylene 35 The above ingredients are mixed and dissolved, diluted with water before use, and sprayed as an emulsion. Example 4 Wettable powder Compound of the present invention 20 parts Higher alcohol sulfuric ester 5 Diatomaceous earth 70 White carbon 5 The above ingredients are mixed and ground into a fine powder, which is diluted with water before use and sprayed as a suspension. Example 5 Powder Compound of the present invention 5 parts Talc 94.6 Silica 0.3 Alkylphenylpolyoxyethylene 0.1 The above are mixed and pulverized, and sprinkled as is when used. It goes without saying that the compound of the present invention is sufficiently effective when used alone, but its adulticidal power is weak, so
It is extremely useful when used in combination with one or more compounds having adulticidal activity against plant-parasitic spider mites. In addition to the compound having adulticidal ability, the compound of the present invention can also be used in combination with one or more of various agricultural chemicals. Representative examples of acaricides and insecticides that can be used in combination with the compounds of the present invention are shown below. Acaricides (fungicides): BCPE, chlorbenzilate, chlorpropylate, proclonol, fenisobromolate, kersen, dibutone,
binapacryl, chlorphenamidine, amitraz, BPPS, PPPS, benzomate, cyhexatine, distanoxane, polynactin, chinomethionate, thioquinox, CPCBS, tetradifon, tetrasul, cycloplate, kayaside, kayahope, 3-n-dodecyl-1,
4-naphthoquinone-2-yl acetate, polysulfide lime, organophosphorus insecticides (acaricides): fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, vamidethion, fenthoate, dimethoate, formothion, marathon, dipterex, thiometone, phosmet, Menazone, dichlorvos, acephate, EPBP, diaryfol, methyl parathion, oxydimethone methyl, ethion, aldicarp, propoxyyul, pyrethroid insecticides (acaricides): permethrin, cypermethrin, decamethrin, fuenvalerate, fuenpropathrin, pyrethrin, Allethrin, Tetramethrin, Resmethrin, Parsulin, Dimethrin, Propasurin,
Prosulin, 3-phenoxybenzyl-2,2-dichloro-1-(4-ethoxyphenyl)-1-cyclopropanecarboxylate, α-cyano-3-phenoxybenzyl 2,2
-dichloro-1-(4-ethoxyphenyl)-1
-cyclopropanecarboxylate, (RS)-α-cyano-3-phenoxybenzyl (RS)-2-(4-trichloromethoxyphenyl)-3-methylbutyrate, (RS)-α-cyano-3 -Phenoxybenzyl (RS)-2-(2-chloro-4-trichloromethylanilino)-3-methylbutyrate Machine oil. Next, a test example will be given to demonstrate the acaricidal activity of the compound of the present invention. Test Example 1 Efficacy against two-spotted spider mites Thirty female adult two-spotted spider mites resistant to organic phosphorus agents were inoculated onto the first true leaves of green beans that had been sown in 2-inch pots 7 to 10 days after germination. According to the emulsion formulation shown in Example 3, the emulsion was diluted with water to a compound concentration of 500 and 125 ppm, and then sprayed. Three days after spraying, the killing rate was determined, and adults were removed and eggs laid during these three days were evaluated.
A check was made on the 11th day to see if the insects had grown to adulthood, and the degree of acaricidal effectiveness was determined. The results are as follows.
【表】【table】
【表】
なお、殺ダニ有効度は次式により求めた。
殺ダニ有効度％
無処理区成虫数−処理区成虫数
＝[Table] The acaricidal effectiveness was calculated using the following formula.
Acaricidal effectiveness%
Number of adults in untreated area - Number of adults in treated area =
Claims (1)
R1は低級アルキル基を、R2は異項原子として１
個の酸素原子又は硫黄原子を有する五員複素環又
はフエニル基又はモノもしくはジC1〜12アルキル
基、ハロゲン原子、ハロアルキル基、アルコキシ
基もしくはメチレンジオキシ基置換フエニル基
を、R3は置換基を有しもしくは有せざるC5〜7の
シクロアルキル基、シクロアルケニル基、又は酸
素原子、硫黄原子、窒素原子の少なくとも１種を
有する複素環を示す。但し、R1がメチル基を、
R2がメチル基モノ置換フエニル基を、Ｙ及びＺ
が夫々酸素原子を示すときR3はシクロヘキシル
基ではない。）で表される化合物のトランス体。 ２ 一般式 （式中、Ｙは酸素原子、又は硫黄原子を、R1
は低級アルキル基を、R2は異項原子として１個
の酸素原子又は硫黄原子を有する五員複素環又は
フエニル基又はモノもしくはジC1〜12アルキル基
ハロゲン原子、ハロアルキル基、アルコキシ基も
しくはメチレンジオキシ基置換フエニル基を示
す。）で表される化合物のトランス体と、一般式 R3−NCZ （式中、Ｚは酸素原子又は硫黄原子を、R3は
置換基を有しもしくは有せざるC5〜7のシクロアル
キル基、シクロアルケニル基又は酸素原子、硫黄
原子、窒素原子の少なくとも１種を有する複素環
を示す）。で表される（チオ）イソシアナート類
と反応させることを特徴とする一般式 （式中、Ｙ，Ｚ，R1，R2、及びR3は前記と同
一の意味を示す。但し、R1がメチル基を、R2が
メチル基モノ置換フエニル基を、Ｙ及びＺが夫々
酸素原子を示すときR3はシクロヘキシル基では
ない。）で表される化合物のトランス体の製造方
法。 ３ 一般式 （式中、Ｚは酸素原子又は硫黄原子を、R1は
低級アルキル基を、R2は異項原子として１個の
酸素原子又は硫黄原子を有する五員複素環又はフ
エニル基またはモノもしくは、ジC1〜12アルキル
基、ハロゲン原子、ハロアルキル基、アルコキシ
基、もしくはメチレンジオキシ基置換フエニル基
を、R3は置換基を有しもしくは有せざるC5〜7の
シクロアルキル基、シクロアルケニル基、又は酸
素原子、硫黄原子、窒素原子の少なくとも１種を
有する複素環を示す。）で表される化合物と（チ
オ）カルボニル化試薬とを反応させることを特徴
とする一般式 （式中、R1，R2，R3、Ｚは前記と同一の意味
をし、Ｙは酸素原子又は硫黄原子を示す。但し、
R1がメチル基を、R2がメチル基モノ置換フエニ
ル基を、ＹおよびＺが夫々酸素原子を示すとき、
R3はシクロヘキシル基ではない。）で表される化
合物のトランス体の製造方法。 ４ 一般式 （式中、Ｙ，Ｚは酸素原子、又は硫黄原子を、
を示し、R1は低級アルキル基を、R2は異項原子
として１個の酸素原子又は硫黄原子を有する五員
複素環又はフエニル基又はモノもしくはジC1〜12
アルキル基、ハロゲン原子、ハロアルキル基、ア
ルコキシ基もしくはメチレンジオキシ基置換フエ
ニル基を、R3は置換基を有しもしくは有せざる
C5〜7のシクロアルキル基、シクロアルケニル基、
又は酸素原子、硫黄原子、窒素原子の少なくとも
１種を有する複素環を示す。但し、R1がメチル
基を、R2がメチル基モノ置換フエニル基を、Ｙ
及びＺが夫々酸素原子を示すときR3はシクロヘ
キシル基ではない。）で表される化合物のトラン
ス体を有効成分として含有することを特徴とする
殺ダニ剤。[Claims] 1. General formula (In the formula, Y and Z are oxygen atoms or sulfur atoms,
R 1 is a lower alkyl group, R 2 is 1 as a foreign atom
R 3 is a substituent ; a five-membered heterocycle having 5 oxygen atoms or sulfur atoms; represents a C5-7 cycloalkyl group, a cycloalkenyl group, or a heterocycle having at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. However, if R 1 is a methyl group,
R 2 is a methyl group monosubstituted phenyl group, Y and Z
When each represents an oxygen atom, R 3 is not a cyclohexyl group. ) is the trans isomer of the compound represented by 2 General formula (In the formula, Y is an oxygen atom or a sulfur atom, R 1
is a lower alkyl group, R 2 is a five-membered heterocycle having one oxygen atom or sulfur atom as a foreign atom, or a phenyl group, or a mono- or di-C 1-12 alkyl group, a halogen atom, a haloalkyl group, an alkoxy group, or methylene Indicates a dioxy group-substituted phenyl group. ) and the trans isomer of a compound represented by the general formula R 3 -NCZ (wherein, Z is an oxygen atom or a sulfur atom, and R 3 is a C 5-7 cycloalkyl group with or without a substituent. , a cycloalkenyl group, or a heterocycle containing at least one of an oxygen atom, a sulfur atom, and a nitrogen atom). General formula characterized by reaction with (thio)isocyanates represented by (In the formula, Y, Z, R 1 , R 2 and R 3 have the same meanings as above. However, R 1 is a methyl group, R 2 is a methyl monosubstituted phenyl group, and Y and Z are A method for producing a trans isomer of a compound represented by (R 3 is not a cyclohexyl group when each represents an oxygen atom). 3 General formula (In the formula, Z is an oxygen atom or a sulfur atom, R 1 is a lower alkyl group, and R 2 is a five-membered heterocycle having one oxygen or sulfur atom as a foreign atom, a phenyl group, or a mono- or di- C 1-12 alkyl group, halogen atom, haloalkyl group, alkoxy group, or methylenedioxy group-substituted phenyl group, R 3 is a C 5-7 cycloalkyl group, cycloalkenyl group with or without a substituent , or a heterocyclic ring having at least one of an oxygen atom, a sulfur atom, and a nitrogen atom) and a (thio)carbonylation reagent. (In the formula, R 1 , R 2 , R 3 , and Z have the same meanings as above, and Y represents an oxygen atom or a sulfur atom. However,
When R 1 represents a methyl group, R 2 represents a methyl monosubstituted phenyl group, and Y and Z each represent an oxygen atom,
R 3 is not a cyclohexyl group. ) A method for producing a trans isomer of a compound represented by 4 General formula (In the formula, Y and Z are oxygen atoms or sulfur atoms,
, R 1 is a lower alkyl group, R 2 is a five-membered heterocycle having one oxygen atom or sulfur atom as a foreign atom, or a phenyl group, or a mono- or di-C 1-12
an alkyl group, a halogen atom, a haloalkyl group, an alkoxy group, or a phenyl group substituted with a methylenedioxy group, and R 3 has or does not have a substituent.
C5-7 cycloalkyl group, cycloalkenyl group,
Alternatively, it represents a heterocycle containing at least one of an oxygen atom, a sulfur atom, and a nitrogen atom. However, R 1 is a methyl group, R 2 is a methyl monosubstituted phenyl group, and Y
and Z each represent an oxygen atom, R 3 is not a cyclohexyl group. ) A miticide characterized by containing the trans isomer of the compound represented by () as an active ingredient.
Priority Applications (35)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5036380A JPS56156270A (en) | 1980-04-18 | 1980-04-18 | Heterocyclic compound, its preparation and acaricide |
| IL61016A IL61016A (en) | 1979-10-03 | 1980-09-10 | 3-carboxamide(or carbothiamide)derivatives of oxazolidine and thiazolidine-2-one(or 2-thione),their preparation and acaricidal compositions containing them |
| NZ194913A NZ194913A (en) | 1979-10-03 | 1980-09-10 | Trans-4,5-disubstituted-3-substituted (thio)carbamoyl-(oxazolidin or thiazolidin)-2-(thio)ones |
| GR62867A GR70207B (en) | 1979-10-03 | 1980-09-11 | |
| YU02375/80A YU237580A (en) | 1979-10-03 | 1980-09-17 | Process for obtaining new oxazidone and thiozolidone derivatives |
| AU62561/80A AU518432B2 (en) | 1979-10-03 | 1980-09-19 | 3,4,5-trisubstituted-oxazolid and thiazolid-2-ones |
| CA000360802A CA1152078A (en) | 1979-10-03 | 1980-09-23 | Oxazolidine and thiazolidine derivatives and preparation thereof |
| GB8030806A GB2059961B (en) | 1979-10-03 | 1980-09-24 | 3-carbomovloxazolidone and thiazolidone derivatives having acaricidal activity |
| NLAANVRAGE8005354,A NL188576C (en) | 1979-10-03 | 1980-09-25 | CARBAMOYLOXAZOLID DERIVATIVES WITH PESTICIDE ACTION AND ACARICIDE PREPARATIONS CONTAINING SUCH COMPOUNDS. |
| IT8049757A IT1207140B (en) | 1979-10-03 | 1980-09-26 | OF THESE COMPOUNDS HETEROCYCLIC COMPOUNDS AND AACARICIDE COMPOSITIONS OBTAINED BY MIXTURES |
| TR20667A TR20667A (en) | 1979-10-03 | 1980-09-30 | HETEROCYCLIC COMPOSITIONS USEFUL AS AN AKARISID |
| BR8006295A BR8006295A (en) | 1979-10-03 | 1980-09-30 | HETEROCYCLICAL COMPOUND, ACARICIDE COMPOSITION AND PROCESS FOR THE PREPARATION OF THAT COMPOUND |
| PL1980227020A PL125287B1 (en) | 1979-10-03 | 1980-10-01 | Acaricide and method of manufacture of derivatives of 3-carbamyloxazolidones and 3-carbamylthiazolidones |
| CS806625A CS216542B2 (en) | 1979-10-03 | 1980-10-01 | Acaricide means and method of preparation of active substances |
| EG603/80A EG14517A (en) | 1979-10-03 | 1980-10-01 | Process for preparation heterocyclie compound its producing as acaricidal agent |
| DE3037105A DE3037105C2 (en) | 1979-10-03 | 1980-10-01 | Oxazolidone and thiazolidone derivatives, processes for their preparation and their use |
| RO108583A RO85287B (en) | 1979-10-03 | 1980-10-02 | Acaricidal composition |
| MX10152080U MX6510E (en) | 1979-10-03 | 1980-10-02 | PROCEDURE FOR PREPARING OXAZOLIDONE AND THIAZOLIDONE DERIVATIVES |
| RO108584A RO84096B (en) | 1979-10-03 | 1980-10-02 | Process for preparing some heterocyclic derivatives |
| SU802987322A SU1391489A3 (en) | 1979-10-03 | 1980-10-02 | Acaricide compound in the form of fluid suspension concentrate |
| FR8021131A FR2466463A1 (en) | 1979-10-03 | 1980-10-02 | HETEROCYCLIC COMPOUNDS, CONTAINING ACARICIDE COMPOSITION AND PROCESS FOR PREPARING THE SAME |
| RO80102267A RO80247A (en) | 1979-10-03 | 1980-10-02 | ACARICIDA COMPOSITION |
| RO108585A RO84095B (en) | 1979-10-03 | 1980-10-02 | Process for preparing some heterocyclic derivatives |
| ES495586A ES495586A0 (en) | 1979-10-03 | 1980-10-02 | A PROCEDURE FOR THE PREPARATION OF OXAZO- LIDONA- OR TIAZOLIDONE DERIVATIVES. |
| MX825080A MX156579A (en) | 1979-10-03 | 1980-10-02 | PROCEDURE FOR PREPARING OXAZOLIDONE AND THIAZOLIDONE DERIVATIVES |
| PT71864A PT71864B (en) | 1979-10-03 | 1980-10-02 | PROCESS FOR THE PREPARATION OF HETHEROCICLIC COMPOUNDS |
| HU802417A HU187312B (en) | 1979-10-03 | 1980-10-03 | Acaricide compositions and process for producing heterocyclic compounds |
| CH742280A CH645886A5 (en) | 1979-10-03 | 1980-10-03 | HETEROCYCLIC COMPOUNDS. |
| AR282763A AR226573A1 (en) | 1979-10-03 | 1980-10-03 | NEW DERIVATIVES OF 4-ALKYL (C1-4) -3- (TIO) -CARBAMOIL-OXA OR TIA) ZOLIDIN-2- (TI) -ONA PROCEDURES FOR PREPARING THEM AND ACARICIDAL COMPOSITIONS THAT CONTAIN THEM |
| SU813265693A SU999970A3 (en) | 1980-04-18 | 1981-04-07 | Process for producing heterocyclic compounds |
| SU823381349A SU1075974A3 (en) | 1979-10-03 | 1982-01-28 | Process for preparing heterocyclic compounds |
| US06/348,757 US4431814A (en) | 1979-10-03 | 1982-02-16 | Heterocyclic compounds |
| US06/350,368 US4442116A (en) | 1979-10-03 | 1982-02-19 | Heterocyclic compounds |
| YU2597/82A YU42817B (en) | 1979-10-03 | 1982-11-22 | Process for obtaining new derivatives of oxazolidone and thiazolidone |
| CA000455945A CA1183536B (en) | 1979-10-03 | 1984-06-05 | Oxazolidine and thiazolidine derivatives and preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5036380A JPS56156270A (en) | 1980-04-18 | 1980-04-18 | Heterocyclic compound, its preparation and acaricide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56156270A JPS56156270A (en) | 1981-12-02 |
| JPH0215545B2 true JPH0215545B2 (en) | 1990-04-12 |
Family
ID=12856801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5036380A Granted JPS56156270A (en) | 1979-10-03 | 1980-04-18 | Heterocyclic compound, its preparation and acaricide |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS56156270A (en) |
| SU (1) | SU999970A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0439163U (en) * | 1990-07-31 | 1992-04-02 |
-
1980
- 1980-04-18 JP JP5036380A patent/JPS56156270A/en active Granted
-
1981
- 1981-04-07 SU SU813265693A patent/SU999970A3/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0439163U (en) * | 1990-07-31 | 1992-04-02 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56156270A (en) | 1981-12-02 |
| SU999970A3 (en) | 1983-02-23 |
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