JPH02152964A - Ureidocarbamate derivative and herbicide containing the same as active ingredient - Google Patents
Ureidocarbamate derivative and herbicide containing the same as active ingredientInfo
- Publication number
- JPH02152964A JPH02152964A JP30615388A JP30615388A JPH02152964A JP H02152964 A JPH02152964 A JP H02152964A JP 30615388 A JP30615388 A JP 30615388A JP 30615388 A JP30615388 A JP 30615388A JP H02152964 A JPH02152964 A JP H02152964A
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- present
- compound
- ureidocarbamate
- 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.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title claims abstract description 25
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 22
- FTJHKZQHQDKPFJ-UHFFFAOYSA-N (carbamoylamino)carbamic acid Chemical class NC(=O)NNC(O)=O FTJHKZQHQDKPFJ-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000004480 active ingredient Substances 0.000 title claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- XCGWUIXOGKKOEY-UHFFFAOYSA-N (carbamoylamino) carbamate Chemical class NC(=O)NOC(N)=O XCGWUIXOGKKOEY-UHFFFAOYSA-N 0.000 claims description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 27
- -1 3-Aminophenyl N-(6-methoxy-2-pyridyl)-N-ethylthiocarbamate Chemical compound 0.000 abstract description 17
- 240000007594 Oryza sativa Species 0.000 abstract description 7
- 235000021307 Triticum Nutrition 0.000 abstract description 4
- 240000008042 Zea mays Species 0.000 abstract description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 4
- 235000005822 corn Nutrition 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 235000010469 Glycine max Nutrition 0.000 abstract description 3
- 244000068988 Glycine max Species 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 241000209140 Triticum Species 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 230000001629 suppression Effects 0.000 description 6
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 244000301850 Cupressus sempervirens Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 240000001341 Reynoutria japonica Species 0.000 description 3
- 235000018167 Reynoutria japonica Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 2
- DCTOHCCUXLBQMS-UHFFFAOYSA-N 1-undecene Chemical compound CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 240000003173 Drymaria cordata Species 0.000 description 2
- 240000001549 Ipomoea eriocarpa Species 0.000 description 2
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- 229960001413 acetanilide Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RRNGFPNDTJUIGS-UHFFFAOYSA-N (3,4-dichlorophenyl) carbamate Chemical compound NC(=O)OC1=CC=C(Cl)C(Cl)=C1 RRNGFPNDTJUIGS-UHFFFAOYSA-N 0.000 description 1
- UBMONMNZSGNXMV-UHFFFAOYSA-N (3-aminophenyl) carbamate Chemical class NC(=O)OC1=CC=CC(N)=C1 UBMONMNZSGNXMV-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- ILOZECIQNMSVCK-UHFFFAOYSA-N 4-methyl-n,n-dipropylaniline Chemical compound CCCN(CCC)C1=CC=C(C)C=C1 ILOZECIQNMSVCK-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 235000004405 Ageratum conyzoides Nutrition 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 240000008564 Boehmeria nivea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IWAFIJBVEFQJLS-UHFFFAOYSA-N C1=CC=NC=C1.[Cl+] Chemical compound C1=CC=NC=C1.[Cl+] IWAFIJBVEFQJLS-UHFFFAOYSA-N 0.000 description 1
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 1
- 240000008867 Capsella bursa-pastoris Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000006719 Cassia obtusifolia Nutrition 0.000 description 1
- 244000277285 Cassia obtusifolia Species 0.000 description 1
- 241001335577 Ceratophyllum echinatum Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 240000000005 Chenopodium berlandieri Species 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000008495 Chrysanthemum leucanthemum Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009852 Cucurbita pepo Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 241000428981 Dyssodia Species 0.000 description 1
- 244000058871 Echinochloa crus-galli Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000758791 Juglandaceae Species 0.000 description 1
- 240000000486 Lepidium draba Species 0.000 description 1
- 235000000391 Lepidium draba Nutrition 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 235000013939 Malva Nutrition 0.000 description 1
- 240000000982 Malva neglecta Species 0.000 description 1
- 235000000060 Malva neglecta Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000003805 Musa ABB Group Nutrition 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 1
- LVKTWOXHRYGDMM-UHFFFAOYSA-N Naproanilide Chemical compound C=1C=C2C=CC=CC2=CC=1OC(C)C(=O)NC1=CC=CC=C1 LVKTWOXHRYGDMM-UHFFFAOYSA-N 0.000 description 1
- 240000007019 Oxalis corniculata Species 0.000 description 1
- 235000016499 Oxalis corniculata Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000237509 Patinopecten sp. Species 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000015266 Plantago major Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 244000184734 Pyrus japonica Species 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 235000012255 calcium oxide Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- ZWWAJMUJXCLKDI-UHFFFAOYSA-N ethylsulfanyl carbamate Chemical compound C(N)(=O)OSCC ZWWAJMUJXCLKDI-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000002421 finishing Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- OXHDYFKENBXUEM-UHFFFAOYSA-N glyphosine Chemical compound OC(=O)CN(CP(O)(O)=O)CP(O)(O)=O OXHDYFKENBXUEM-UHFFFAOYSA-N 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 239000011419 magnesium lime Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 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
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000013459 phenoxy herbicide Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 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
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- DOMJXQKSEROFFV-UHFFFAOYSA-N s-(3-nitrophenyl) chloromethanethioate Chemical compound [O-][N+](=O)C1=CC=CC(SC(Cl)=O)=C1 DOMJXQKSEROFFV-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
【発明の詳細な説明】
[産業上の利用分野]
本発明は新規なウレイドカーバメート誘導体およびそれ
をR効成分として含有する除草剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a novel ureidocarbamate derivative and a herbicide containing the same as an R active ingredient.
[従来の技術]
従来より、ウレイドカーバメート誘導体の除草活性は知
られており、例えばファーム ケミカルズ ハンドブッ
ク 88、C128にはカルブチレ−1・が示されてい
る。[Prior Art] The herbicidal activity of ureidocarbamate derivatives has been known, for example, Carbutyre-1 is shown in Farm Chemicals Handbook 88, C128.
しかしながら、従来のウレイドカーバメート誘・6体は
除草活性が必ずしも十分ではないか、あるいは作物・雑
苧間の選択性が十分でなく、従って、作物に々・Iする
安全性に問題がある。However, conventional ureidocarbamate derivatives do not necessarily have sufficient herbicidal activity or have insufficient selectivity between crops and weeds, and therefore pose a problem in terms of safety when applied to crops.
[発明が解決しようとする課題]
本発明の目的は、除車剤として用いた場合に除草活性が
高くかつ作物に対する安全性の高い新規化合物およびそ
れを有効成分とする新規な除草剤を提1共することであ
る。[Problems to be Solved by the Invention] An object of the present invention is to provide a new compound that has high herbicidal activity and high safety for crops when used as a car remover, and a new herbicide containing the same as an active ingredient. It is about sharing.
[課題を解決するための手段および作用]本発明者らは
、鋭意研究を重ねた結果、新規なウレイドカーバメート
誘導体がきわめて優れた除’+I:?+’i性と選択性
をもつことを見いだし本発明を完1戊した。[Means and effects for solving the problem] As a result of intensive research, the present inventors have found that a new ureido carbamate derivative has an extremely excellent ability to remove '+I:? It was discovered that the present invention has +'i property and selectivity, and the present invention has been completed.
すなイ〕ち、本発明は、一般式[I]
(たたし、YY は酸素原子または硫黄原子を示し、
Y Y2は同一でも異なっていてもよい。Rは水素)
t’it TまたはCI−CBアルキル基を示し、Rは
C,−C6アルキルチオ基またはC,−C6アルコキシ
基を示し、AはNR3R’(ただし、R、Rは水素原子
、C1Ce フルキルU、C−C8アルキルチオ基、C
1−C[
Bアルコキシ基、C1−C6アルケニル基またはアリー
ル基を示し、R、Rは同一でも異なり■は1〜10の整
数を示す。)または
(ただし、Y3
は酸素原子または硫黄原子を示し、
Ill、11は1〜10の整数を示す。)を示す。)で
7」(されるウレイドカーバメート誘導体(以下、本発
明化合物という)、および、上記一般式[1]て示され
る本発明化合物を有効成分として含有する除つ剤を提供
するものである。In other words, the present invention is based on the general formula [I] (where YY represents an oxygen atom or a sulfur atom,
Y Y2 may be the same or different. R is hydrogen)
t'it T or CI-CB alkyl group, R represents C, -C6 alkylthio group or C, -C6 alkoxy group, A is NR3R' (however, R, R are hydrogen atoms, C1Ce furkyl U, C -C8 alkylthio group, C
1-C[B represents an alkoxy group, a C1-C6 alkenyl group, or an aryl group, R and R may be the same or different, and ■ represents an integer of 1 to 10. ) or (wherein, Y3 represents an oxygen atom or a sulfur atom, and Ill and 11 represent an integer of 1 to 10). ) and a ureido carbamate derivative (hereinafter referred to as the compound of the present invention) which is represented by the above general formula [1] as an active ingredient.
本発明により、除草剤として優れた除草活性および安全
性を白°する新規化合物が提供された。The present invention provides a novel compound that exhibits excellent herbicidal activity and safety as a herbicide.
また、本発明化合物を有効成分として含有する本<6明
の除草剤は、後述する実施例で明らかになるように、種
々の雑?Sを的確に駆除することができる除〆jで活性
の高いものであり、それでいて種々の作物、特にイネ、
コムギ、トウモロコシ、ダイス9には、極めて安全に使
用できる安全性の高いものである。In addition, the herbicide of this invention containing the compound of the present invention as an active ingredient can be used in various miscellaneous herbicides, as will be made clear in the Examples described below. It is a highly active exterminator that can accurately exterminate S., and is effective against various crops, especially rice,
It is highly safe and can be used extremely safely for wheat, corn, and dice 9.
表1、表2および表3に本発明の好ましい具体例を示す
が、本発明の化合物はこれらに限定されるものではない
。Preferred specific examples of the present invention are shown in Tables 1, 2, and 3, but the compounds of the present invention are not limited thereto.
表
つづき
表
表
上記本発明化合物は種々の方法で製造することができる
が、
例えば下記反応式に基づいて製造す
ることができる。Table Continued Table The above-mentioned compound of the present invention can be produced by various methods, but for example, it can be produced based on the following reaction formula.
[11]
[m]
一般式
[
]
[]
[]
一般式
[
■
]
[VI]
[■〕
−一般式[I]
%式%
一 一般式[11(4)
上記反応式中一般式[tl] 一般式[■] −般式
[IV] 一般式[V] 一般式[■] 一般式[
■]、一般式[■]または一般式[IX]中のy I
y 2 RI R2およびAは一般式[1]と同
じものを示し、一般式[■]、一般式[■]または一般
式[■]中のXlはハロゲン原子を示す。ハロゲン原子
として好ましくは、塩素原子あるいは臭素原rをあげる
ことができる。[11] [m] General formula [ ] [] [] General formula [■] [VI] [■] - General formula [I] % formula % - General formula [11(4) General formula [tl] in the above reaction formula ] General formula [■] - General formula [IV] General formula [V] General formula [■] General formula [
■], y I in general formula [■] or general formula [IX]
y 2 RI R2 and A are the same as those in the general formula [1], and Xl in the general formula [■], the general formula [■], or the general formula [■] represents a halogen atom. Preferably, the halogen atom is a chlorine atom or a bromine atom r.
上記反応は、溶媒中でまたは無溶媒下で、塩基(i(1
0ド゛Cまたは塩基非存在下で、好ましくは0℃から1
.50℃、さらに好ましくは20℃から100℃で数分
から48時間反応させることにより行うことができる。The above reaction is carried out in a solvent or without solvent with a base (i(1
0°C or in the absence of a base, preferably from 0°C to 1
.. This can be carried out by reacting at 50°C, more preferably from 20°C to 100°C for several minutes to 48 hours.
反応に用いられる溶媒として、アセトン、メチルエチル
ケトン等のケトン類;ベンゼン、トルエン、キシレン等
の芳δ族炭化水素類;エチルエーテル、テトラヒドロフ
ラン、ジオキサン等のエーテル類;クロロベンゼン、ク
ロロホルム、四塩化炭素、ジクロロエタン、ジクロロメ
タン等のハロゲン化炭化水素類;トリエチルアミン、ピ
リジン、ジメチルアニリン等の第三級アミン;およびア
セトニトリル、ジメチルホルムアミド、ジメチルスルホ
キシド、リン酸へキサメチルトリアミド等の極性溶媒等
を挙げることができる。As a solvent used in the reaction, ketones such as acetone and methyl ethyl ketone; aromatic δ group hydrocarbons such as benzene, toluene, and xylene; ethers such as ethyl ether, tetrahydrofuran, and dioxane; chlorobenzene, chloroform, carbon tetrachloride, dichloroethane, Examples include halogenated hydrocarbons such as dichloromethane; tertiary amines such as triethylamine, pyridine, and dimethylaniline; and polar solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide, and hexamethyltriamide phosphate.
また、反応に用いられる塩基としてトリエチルアミン、
ピリジン、1.8−ジアザビシクロ[5゜4.01−7
−ウンデセン、ジメチルアニリン等の第五級アミン;水
酸化ナトリウム、水酸化カリウム等の水酸化アルカリ;
水酸化カルシウム等の水酸化アルカリ土類;炭酸ナトリ
ウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カ
リウム等の炭酸アルカリ塩および水素化ナトリウムのよ
うな水素化金属等を挙げることができる。In addition, triethylamine, as a base used in the reaction,
Pyridine, 1,8-diazabicyclo[5゜4.01-7
-Quaternary amines such as undecene and dimethylaniline; alkali hydroxides such as sodium hydroxide and potassium hydroxide;
Examples include alkaline earth hydroxides such as calcium hydroxide; alkali carbonates such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, and potassium hydrogen carbonate; and metal hydrides such as sodium hydride.
反応に(!ζされる試剤の量は、反応(1゛)において
は通常、一般式[11]の化合物1当量に対して一般式
[I11]の化合物1当量から10当量、塩基は1当量
から10当量であり、反応(2)においては通常、一般
式[IV]の化合物1′5量に対して一般式[V]の化
合物1当量から10当瓜、塩基は1゛11量から101
L′1量であり、反応(3)においては通常、一般式C
VIIの化合物1当量に対して一般式[■]の化合物1
当量から10当量、塩基はi j’j Hから10当量
であり、反応(4)においては通常、一般式[■]の化
合物1当量に対して一般式[IX]の化合物1当量から
10当量、塩基は1711量から10当量である。In reaction (1゛), the amount of reagent used in the reaction (!ζ) is usually 1 to 10 equivalents of the compound of general formula [I11] per 1 equivalent of the compound of general formula [11], and 1 equivalent of the base. In reaction (2), usually 1 to 10 equivalents of the compound of general formula [V] and 1 to 10 equivalents of the base are used per 1'5 amounts of the compound of general formula [IV], and 10 equivalents of the base.
L′1 amount, and in reaction (3), the general formula C
Compound 1 of general formula [■] per equivalent of compound VII
The base is 10 equivalents from i j'j H, and in reaction (4), usually 1 equivalent to 10 equivalents of the compound of general formula [IX] is used for 1 equivalent of the compound of general formula [■]. , the base is 1711 to 10 equivalents.
本発明化合物の原料物質は、−数的な方法で得られる。The raw materials for the compounds of the present invention are obtained by -numerical methods.
例えば、一般式[■]で表される3−アミノフェニル
カーバメート誘導体は、3−ニトロフェニル りロロホ
ーメート誘導体とアミノピリジン誘う体を塩基存在下で
反応させ、さらに還元を行うことによって得ることがで
きる。For example, 3-aminophenyl represented by the general formula [■]
The carbamate derivative can be obtained by reacting a 3-nitrophenyl lyloloformate derivative with an aminopyridine derivative in the presence of a base, and further reducing the reaction mixture.
また、一般式[IV]で表される3−イソシアナートフ
ェニル カーバメート誘導体は、一般式[11]で表さ
れる3−アミノフェニル カーバメート誘導体とホスゲ
ン等と反応させることによって得ることができる。Further, the 3-isocyanatophenyl carbamate derivative represented by the general formula [IV] can be obtained by reacting the 3-aminophenyl carbamate derivative represented by the general formula [11] with phosgene or the like.
本発明化合物をU効成分として含む本発明の除苧剤は、
種々の雑草に対して除草活性をaするが、特に畑地広葉
雑草に対して優れた除草活性を有する。そのような雑位
としては、例えば、アオビユ、スベリヒュ、オナモミ、
センダングサ、ブタフサ、アレチウリ、コアカザ、シロ
ザ、サナエタデ、オオイヌタデ、ハコベ、ナズナ、ミミ
ナグサ、シロバナチョウセンアサガオ、アメリカツノク
サネム、エビスグサ、マルバアサガオ、イヌホウズキ、
ワルナスビ、ホトケノザ、オオバコ、イチビ、アメリカ
キンコジカ、カタバミ、ヤエムグラ、ソバカズラ、イヌ
ノフグリ、オオアレチノギク、ヒメムカシヨモギ、ヒメ
ジオン、ハキダメギク等を挙げることができる。The moth remover of the present invention containing the compound of the present invention as a U-active ingredient,
It has a herbicidal activity against various weeds, but it has particularly excellent herbicidal activity against broad-leaved weeds in upland areas. Examples of such miscellaneous species include Aobiyu, Purslane, Onamomi,
Sendangusa, pigweed, red gourd, koakaza, whiteweed, Japanese knotweed, Japanese knotweed, chickweed, shepherd's purse, Japanese knotweed, white-breasted morning glory, American hornwort, Ebisugusa, Malva morning glory, Japanese dogweed,
Examples of the examples include walnuts, hotokenoza, plantain, ichibia, American cypress, oxalis, japonica, buckwheat, dog's lily, chinensis, wormwood, serpentine, and chinensis.
また、・本発明の除草剤は、水田において問題となる種
々の雑草、例えばタイヌビエ、アゼナ、キカシグサ、ミ
ゾハコベ、タマガヤツリ、マツバイ、ホタルイ、ミズガ
ヤツリ等の禾本科および広葉雑中にχ−1して侵れた除
苧効力を有する。In addition, the herbicide of the present invention can be used to attack various weeds that are problematic in rice fields, such as Japanese millet, azalea, commonweed, chickweed, Japanese cypress, Japanese cypress, scallop, and other broad-leaved weeds. It has a moth removal effect.
また、本発明の除草剤はトウモロコシ、コムギ、ダイス
、イネ等の作物に対してほとんど薬害を与えることがな
く安全性の高いものである。Furthermore, the herbicide of the present invention is highly safe, causing almost no phytotoxicity to crops such as corn, wheat, soybeans, and rice.
本発明の除草剤は、前記一般式[I]で示される本発明
化合物の一種または二種以上の適当量を、この分野にお
いて通常用いられている農薬補助剤を用いて、Q薬製剤
上一般に行なわれている方法により製剤された、例えば
乳剤、水和剤、油剤、粒剤、粉剤等の製剤形態にして使
用される。これら種々の製剤は実際の使用に際しては、
そのまま使用するか、または水で所定の濃度に希釈して
使用することができる。The herbicide of the present invention is generally prepared by adding an appropriate amount of one or more compounds of the present invention represented by the above general formula [I] to a Q drug formulation using a pesticide adjuvant commonly used in this field. It is used in the form of formulations, such as emulsions, wettable powders, oils, granules, and powders, prepared by the methods currently in use. When these various preparations are actually used,
It can be used as is or diluted with water to a predetermined concentration.
農薬補助剤の例としては、希釈剤、界面活性剤、安定剤
、固若剤、エアゾール用噴霧剤、共力剤、増量剤、固体
担体、効力延長剤、分散安定剤等を挙げることができる
。Examples of pesticide adjuvants include diluents, surfactants, stabilizers, solidifying agents, aerosol sprays, synergists, bulking agents, solid carriers, potency extenders, dispersion stabilizers, etc. .
希釈剤の例としては水、炭化水素類、アルコール類、エ
ーテル類、アルコールエーテル類、ケトン類、エステル
類、アミド類、スルホキシド類、ケロシン、鉱油等を挙
げることができる。Examples of diluents include water, hydrocarbons, alcohols, ethers, alcohol ethers, ketones, esters, amides, sulfoxides, kerosene, mineral oil, and the like.
また、増量剤、固体担体としては無機質粉粒体例えば生
石灰、マグネシウム石灰、石膏、炭酸カルシウム、仕上
、パーライト、軽石、珪藻上、°7′ルミナ、ゼオライ
ト、粘土鉱物(滑石、バーミキュライト、カオリナイト
)、植物粉粒体(例えばデン粉、穀物、ブドウ糖)、合
成樹脂粉体(例えばフェノール樹脂、炭素樹脂、塩化ビ
ニール樹脂)等を挙げることができる。In addition, fillers and solid carriers include inorganic powders such as quicklime, magnesium lime, gypsum, calcium carbonate, finishing, perlite, pumice, diatom, °7' lumina, zeolite, clay minerals (talc, vermiculite, kaolinite). , plant powder (for example, starch, grain, glucose), synthetic resin powder (for example, phenol resin, carbon resin, vinyl chloride resin), and the like.
さらに、界面活性剤としては、アニオン界面活性剤(例
えばアルキル硫酸エステル類、アリールスルホン酸類、
コハク酸塩類、ポリエチレングリコールアルキルアリー
ルエーテル硫酸塩類)、カチオン界面活性剤(例えばア
ルキルアミン類、ポリオキシエチレンアルキルアミン類
)、非イオン界面活性剤(例えばポリオキシエチレング
リコールエーテル類、ポリオキシエチレングリコールエ
ステル類、多価アルコールエステル類)、両性界面活性
剤等を挙げることができる。Furthermore, as surfactants, anionic surfactants (e.g. alkyl sulfates, arylsulfonic acids,
succinates, polyethylene glycol alkylaryl ether sulfates), cationic surfactants (e.g. alkylamines, polyoxyethylene alkyl amines), nonionic surfactants (e.g. polyoxyethylene glycol ethers, polyoxyethylene glycol esters) esters, polyhydric alcohol esters), amphoteric surfactants, and the like.
本発明の除草剤は、通常の除草剤と同様にして使用する
ことができ、例えば水田雑草に対しては例えば水稲の移
植活若後に雑草の発生前または発生直後にこの発明の除
り剤を用いて土壌処理を行なうことができる。また、畑
地雑草の発芽前または発’J lJJ期にこの発明の除
草剤を用いて土壌処理または茎葉処理を行なうことがで
きる。The herbicide of the present invention can be used in the same manner as ordinary herbicides. For example, for paddy field weeds, the herbicide of the present invention may be used before or immediately after the weeds emerge after transplanting of paddy rice. It can be used for soil treatment. In addition, the herbicide of the present invention can be used to treat soil or foliage before the germination of upland weeds or during the 'JlJJ' stage.
本発明の除草剤の施用量は、施用する方法、目的、施用
時期、雑卓の発生状況により適宜選択することができる
が、通常、1ヘクタール当たり有効成分量で10g〜1
0 kg、好ましくは50g〜5kgである。The amount of the herbicide of the present invention to be applied can be appropriately selected depending on the method of application, purpose, timing of application, and the occurrence of grasshoppers, but it is usually 10g to 1% of the active ingredient per hectare.
0 kg, preferably 50 g to 5 kg.
本発明化合物は、除草剤としての効力向上をめざし、他
の除草剤との混合使用も可能であり、場合によっては、
相乗効果を期待することもできる。The compound of the present invention can be used in combination with other herbicides in order to improve its effectiveness as a herbicide, and in some cases,
A synergistic effect can also be expected.
この例としては、例えば2.4−ジクロルフェノキシ酢
酸:2−メチル−4−クロルフェノキシ酪酸;2−メチ
ル−4−クロルフェノキシ酢酸(エステル、塩類を含む
)等のフェノキシ系除草剤、2.4−’)クロルフェニ
ル−4′−二トロフェニルエーテル、2,4.6−)リ
クロルフェニル=4°−ニトロフェニルエーテル;2−
クロル−4−トリフルオロメチルフェニル−3′ −エ
トキシ−4°−二トロフェニルエーテル;2.4−ジク
ロルフェニル−4゛ −二トロー3° −メトキシフェ
ニルニー7−ル;2,4−ジクロルフェニル−3゜−メ
トキシ力ルボニルー4′ −二トロフェニルエーテル等
のジフェニルエーテル系除草剤、2−クロル−4,6−
ピスエチルアミノー1,3.5−トリアジン;2−メチ
ルチオ−4,6−ピスイソブロビルアミノー1.3.5
−トリアジン等のトリアジン系除草剤、3− (3,4
−ジクロルフェニル)−1,1−ジメチルウレア;3−
(3,4−ジクロルフェニル)−メトキシ−1−メチ
ルウレア;1−(2,2−ジメチルベンジル)−3−l
)−トリルウレア等の尿素系除草剤、イソプロピル−N
−(3−クロルフェニル)カーバメイト;メチル−N−
(3,4−ジクロルフェニル)カーバメイト等のカーバ
メイト系除草剤、5−(4−クロルベンジル)−N、N
−ジエチルチオールカーバメイト;S−エチル−N、N
−ヘキサメチレンチオールカーバメート等のチオールヵ
ーバメ−1・系除苧剤、3,4−ジクロルプロピオンア
ニリド;N−メトキシメチル−2,6−シエチルーα−
クロルアセトアニリド;2−クロル−2° 6゛−ジ
エチル−N−(ブトキシメチル)−アセトアニリド;2
−クロル−2゛ 6゛ −ジエチル−N(「1−プロ
ポキシエチル)−アセトアニリド;N−クロルアセチル
−N−(2,6−シエチルフエニル)−グリシンエチル
エステル等の酸アニリド系除?S剤、5−ブロム−3−
セカンダリ−ブチル−6−メチルウラシル;3−シクロ
へキシル−5,6−トリメチレンウラシル等のウラシル
系除草剤、1,1゛−ジメチル−4,4゛ −ビスピリ
ジニウムクロライド等のピリジニウム塩素系除草剤、N
、N−ビス(ホスホノメチル)−グリシン、〇−エチル
ー〇−(2−ニトロ−5−メチルフェニル)−N−セカ
ンダリ−ブチルホスホロアミドチオニー1・、5−(2
−メチル−1−ピペリジルカルボニルメチル) 0.0
−ジ−n−ブチルジチオホスフェ−1−;5−(2−メ
チル−1−ピペリジルカルボニルメチル)0.0−ジフ
ェニルジチオホスフェート等のリン系除草剤、α、α。Examples include phenoxy herbicides such as 2.4-dichlorophenoxyacetic acid: 2-methyl-4-chlorophenoxybutyric acid; 2-methyl-4-chlorophenoxyacetic acid (including esters and salts); 4-') Chlorphenyl-4'-nitrophenyl ether, 2,4.6-) Lichlorphenyl = 4°-nitrophenyl ether; 2-
Chlor-4-trifluoromethylphenyl-3'-ethoxy-4°-nitrophenyl ether; 2,4-dichlorophenyl-4'-ditro-3'-methoxyphenyl 7-yl; Diphenyl ether herbicides such as chlorphenyl-3゜-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-4,6-
Pisethylamino-1,3.5-triazine; 2-methylthio-4,6-pisisobrobylamino-1.3.5
- Triazine herbicides such as triazine, 3- (3,4
-dichlorophenyl)-1,1-dimethylurea; 3-
(3,4-dichlorophenyl)-methoxy-1-methylurea; 1-(2,2-dimethylbenzyl)-3-l
)-Urea herbicides such as tolylurea, isopropyl-N
-(3-chlorophenyl)carbamate; methyl-N-
Carbamate herbicides such as (3,4-dichlorophenyl)carbamate, 5-(4-chlorobenzyl)-N,N
-diethylthiol carbamate; S-ethyl-N,N
- Thiolcarbame-1-based moth removal agents such as hexamethylenethiol carbamate, 3,4-dichloropropionanilide; N-methoxymethyl-2,6-ethyl-α-
Chloracetanilide; 2-chloro-2°6-diethyl-N-(butoxymethyl)-acetanilide; 2
-Chlor-2'6'-diethyl-N(1-propoxyethyl)-acetanilide; acid anilide-based removal agent such as N-chloroacetyl-N-(2,6-ethylphenyl)-glycine ethyl ester, 5 -Brom-3-
Secondary-butyl-6-methyluracil; uracil-based herbicides such as 3-cyclohexyl-5,6-trimethyleneuracil, pyridinium chlorine-based herbicides such as 1,1゛-dimethyl-4,4゛-bispyridinium chloride agent, N
, N-bis(phosphonomethyl)-glycine, 〇-ethyl〇-(2-nitro-5-methylphenyl)-N-secondary-butylphosphoroamide thionyi 1., 5-(2
-Methyl-1-piperidylcarbonylmethyl) 0.0
Phosphorus herbicides such as -di-n-butyldithiophosphate-1-;5-(2-methyl-1-piperidylcarbonylmethyl)0.0-diphenyldithiophosphate, α, α.
a−トリフルオロ−2,6−シニトローN、N−ジプロ
ピル−p−トルイジン等のトルイジン系除苧剤、5−タ
ーシャリ−ブチル−3−(2,4−ジクロル−5−イソ
プロポキシフェニル)−1゜3.4−オキサジアジリン
−2−オン;3−イソプロピル−IH−2,1,3−ベ
ンゾチアジアジン−(4)−3H−オン−2,2−ジオ
キシド、α−(β−ナフトキシ)−プロピオンアニライ
ド、4− (2,4−ジクロロベンゾイル)−1,3−
ジメチルピラゾール−5−イル p−トルエンスルホネ
−1・などがあげられるが、これに限られるものではな
い。Toluidine-based moth removal agents such as a-trifluoro-2,6-sinitro N, N-dipropyl-p-toluidine, 5-tert-butyl-3-(2,4-dichloro-5-isopropoxyphenyl)-1゜3.4-Oxadiazilin-2-one; 3-isopropyl-IH-2,1,3-benzothiadiazin-(4)-3H-one-2,2-dioxide, α-(β-naphthoxy)- Propionanilide, 4-(2,4-dichlorobenzoyl)-1,3-
Examples include, but are not limited to, dimethylpyrazol-5-yl p-toluenesulfone-1.
[実施例]
以−ド、実施例により本発明をさらに具体的に説明する
が、本発明はこれらに限定されるものではない。[Examples] Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
実施例1
3−(N’ N’−ジメチルウレイド)フェニル
N−(6−メドキシー2−ピリジル)−N−エチルチオ
カーバメート(化合物番号1)の製造m−ニトロフェニ
ルクロロチオホーメート15gをアセトニトリル100
m1に溶解させ2−エチルアミノ−6−メドキシビリジ
ン10gと炭酸カリウム11.3gを加え室温で3時間
反応させた後、1時間還流した。放冷後、不溶物を濾過
し濾液の溶媒を流去し、希塩酸を加えジクロロメタンで
抽出した。溶媒を留去し3−ニトロフェニルN−(6−
メドキシー2−ピリジル)−N−エチルチオカーバメー
トを得た。この3−二トロフェニル N−(6−メドキ
シー2−ピリジル)N−エチルチオカーバメート2.4
gを濃塩酸15m1とエタノール15m1の混合溶液に
加えた後塩化スズの2水和物7.5gをエタノール15
m1に溶解させた溶液を室温下漬下し、その後40℃で
3時間反応させた。反応終了後、溶媒を留去し残さを水
酸化ナトリウムでアルカリ性にした後、クロロホルムで
抽出した。カラムクロマトグラフィーで単離し3−アミ
ノフェニル N−(6−メドキシー2−ピリジル)−N
−エチルチオカーバメート2.0gを得た。Example 1 3-(N'N'-dimethylureido)phenyl
Preparation of N-(6-medoxy-2-pyridyl)-N-ethylthiocarbamate (Compound No. 1) 15 g of m-nitrophenylchlorothioformate was dissolved in 100 g of acetonitrile.
After adding 10 g of 2-ethylamino-6-medoxyviridine and 11.3 g of potassium carbonate to the solution and reacting at room temperature for 3 hours, the mixture was refluxed for 1 hour. After cooling, insoluble matter was filtered, the solvent of the filtrate was washed away, diluted hydrochloric acid was added, and the mixture was extracted with dichloromethane. The solvent was distilled off and 3-nitrophenyl N-(6-
Medoxy 2-pyridyl)-N-ethylthiocarbamate was obtained. This 3-nitrophenyl N-(6-medoxy-2-pyridyl)N-ethylthiocarbamate 2.4
g to a mixed solution of 15 ml of concentrated hydrochloric acid and 15 ml of ethanol, and then 7.5 g of tin chloride dihydrate was added to 15 ml of ethanol.
The solution dissolved in m1 was soaked at room temperature, and then reacted at 40°C for 3 hours. After the reaction was completed, the solvent was distilled off, the residue was made alkaline with sodium hydroxide, and then extracted with chloroform. Isolated by column chromatography, 3-aminophenyl N-(6-medoxy-2-pyridyl)-N
-2.0 g of ethyl thiocarbamate was obtained.
’H−NMR(溶媒: CDCI 単位:δppn
+ )1.30(L、311.J=711z)、3.[
15(s、211)、3.85(s、311)4.30
(Q、211.J=711z)、6.30−7.37(
Il、711)IR1710cm”
このようにして得た3−アミノフェニル N−(6−メ
ドキシー2−ピリジル)−N−エチルチオカーバメート
1.20gとN、N−ジメチルカルバミルクロリド0
.62gをアセトニトリル10■1に加え、さらに炭酸
カリウム0.80gを加えた後、撹拌しながら16時間
加熱還流した。'H-NMR (solvent: CDCI unit: δppn
+) 1.30 (L, 311.J=711z), 3. [
15 (s, 211), 3.85 (s, 311) 4.30
(Q, 211.J=711z), 6.30-7.37(
1.20 g of 3-aminophenyl N-(6-medoxy-2-pyridyl)-N-ethylthiocarbamate thus obtained and 0 g of N,N-dimethylcarbamyl chloride.
.. After adding 62 g to 10 parts of acetonitrile and further adding 0.80 g of potassium carbonate, the mixture was heated under reflux for 16 hours with stirring.
反応混合物を冷却後、不溶物を濾過し、濾液を減圧流去
したのち、残さをカラムクロマトグラフィーにより精製
し、[i約物0.54gを得た。After cooling the reaction mixture, insoluble materials were filtered, and the filtrate was removed under reduced pressure. The residue was purified by column chromatography to obtain 0.54 g of [i].
融点:132−134℃
’H−NMR(mW; CDCI j11位: δ
ppm )1.25(L、311.J−711z)、2
.95(s、Qll)、3.92(s、311)4.1
2(q、211.J−711z)、(i、50−7.8
0(+n、711)元素骨t’i(”0) ’ C1
8H22N40a Sとして計算値 C;57.73.
II:5.92.N;14.9G実71PI値 C;5
7.50.Il;5.88.N;15.32実施例2
う−(N’ −メトキシN° −メチルウレイド)フ
ェニル N−(6−メドキシー2−ピリジル)−N−エ
チルチオカーバメート(化合物番号2)の製造
′う−アミノフェニル N−(6−メドキシー2−ピリ
ジル)−N−エチルチオカーバメート0゜8’Bをトル
エン10m1に溶解させ室温下ホスゲンを0.35g加
え、その後3時間還流した。Melting point: 132-134°C 'H-NMR (mW; CDCI j11th position: δ
ppm) 1.25 (L, 311.J-711z), 2
.. 95 (s, Qll), 3.92 (s, 311) 4.1
2 (q, 211.J-711z), (i, 50-7.8
0(+n, 711) elemental bone t'i("0) ' C1
Calculated value as 8H22N40a S: C; 57.73.
II:5.92. N; 14.9G actual 71PI value C; 5
7.50. Il; 5.88. N;15.32 Example 2 U-(N'-methoxyN°-methylureido)phenyl Preparation of N-(6-medoxy2-pyridyl)-N-ethylthiocarbamate (Compound No. 2)'U-aminophenyl N-(6-medoxy-2-pyridyl)-N-ethylthiocarbamate 0°8'B was dissolved in 10 ml of toluene, 0.35 g of phosgene was added at room temperature, and the mixture was refluxed for 3 hours.
JIL冷後、溶媒を留去し、3−イソシアナートフェニ
ル N−(6−メドキシー2−ピリジル)−N−エチル
チオカーバメート0.5gを?lIだ。この生成物は、
赤外線吸収スペクトルのΔ詐1定により確認した。After cooling the JIL, the solvent was distilled off, and 0.5 g of 3-isocyanatophenyl N-(6-medoxy 2-pyridyl)-N-ethylthiocarbamate was removed. It's lI. This product is
This was confirmed by determining the Δ value of the infrared absorption spectrum.
このようにして得た3−イソシアナートフェニル N−
(6−メドキシー2−ピリジル)−N−エチルカーバメ
−1−0,85gをアセトニトリル1【〕…lとN−メ
チル N−メトキシアミンの塩酸塩(1,59gと炭酸
カリウム0.83gを加え′う時間加熱還流した。さら
に反応混合物を冷却後、不溶物を濾過、濾液を減圧留去
した後残さをカラムクロマトグラフィーにより精製し目
的物0.50gを得た。3-isocyanatophenyl N- thus obtained
Add 0.85 g of (6-medoxy-2-pyridyl)-N-ethylcarbame-1 to 1[]...l of acetonitrile, 1.59 g of N-methyl N-methoxyamine hydrochloride, and 0.83 g of potassium carbonate. The reaction mixture was heated under reflux for an hour. After cooling the reaction mixture, insoluble materials were filtered, the filtrate was distilled off under reduced pressure, and the residue was purified by column chromatography to obtain 0.50 g of the desired product.
融点:102〜105℃
’H−NMR(溶媒: CDCl 単位:δppm
)1.30(L 、 31. J=711z) 、
3.05(s、 311) 、3.(io(s、311
) 。Melting point: 102-105°C 'H-NMR (Solvent: CDCl Unit: δppm
) 1.30 (L, 31. J=711z),
3.05 (s, 311), 3. (io(s, 311
).
3.85 (s 、 311) 、 4−、25(q、
211. J−711z) 、 0.50−7.80
(s 、 711z)元素分析(%):Cl8H22
N404Sとして計算値 C;55.37.lI;5.
07.N;14.34実Δ−1値 C,55,73,1
+、5.Q4.N;14.1(111目、Qなh゛法に
より得た本発明化合物の代表例とその物性を表4、表5
および表6に示す。3.85 (s, 311), 4-, 25 (q,
211. J-711z), 0.50-7.80
(s, 711z) Elemental analysis (%): Cl8H22
Calculated value as N404S C; 55.37. lI;5.
07. N; 14.34 actual Δ-1 value C, 55, 73, 1
+, 5. Q4. N: 14.1 (111th, Representative examples of the compounds of the present invention obtained by the Q method and their physical properties are shown in Tables 4 and 5.
and shown in Table 6.
実施例3(乳剤)
本発明化合物番号1を5Tfim部、キシレン75重量
部およびツルポール2806B (商品名:東邦化学に
業製)20重量部を均一に撹拌混合して乳剤をiすた。Example 3 (Emulsion) 5 parts of Compound No. 1 of the present invention, 75 parts by weight of xylene, and 20 parts by weight of Tsurupol 2806B (trade name: manufactured by Toho Kagaku Nigyo) were uniformly stirred and mixed to prepare an emulsion.
実施1%I4(水相剤)
本発明化合物番号1を10重量部、ジ−クライト(商品
名ニジ−クライト化学鉱業製)86.5!fi量部、二
二一カルゲンNV−406(商品名=11本浦脂製)2
ifi量部およびディスクゾールWA(商品名:第−工
業製薬製)1.5重量部を混合扮砕して水相剤を得た。Example 1% I4 (aqueous phase agent) 10 parts by weight of Compound No. 1 of the present invention, Zikrite (trade name: Nidikrite Kagaku Mining Co., Ltd.) 86.5%! fi amount part, 221 Calgen NV-406 (product name = 11 Honura Resin) 2
Parts of ifi and 1.5 parts by weight of Discsol WA (trade name: manufactured by Dai-Kogyo Seiyaku Co., Ltd.) were mixed and ground to obtain an aqueous phase agent.
実施例5(粒剤)
本発明化合物番号1を10重量部、ベントナイト5(l
fflfiL部、クニライト(商品名:国峰工業製)3
5重量部および界面活性剤としてツルポール8(10A
(、商品名:東邦化学工業製) 5fff量部を混&
粉砕したのち、水を加え均一に撹拌し、直径0゜7 r
n rnの篩穴から押しだし乾燥後、1〜2mmの長さ
に切断して10%粒剤を得た。Example 5 (granules) 10 parts by weight of compound number 1 of the present invention, bentonite 5 (l
fflfi L part, Kunilite (product name: Kunimine Kogyo) 3
5 parts by weight and Tsurupol 8 (10A) as a surfactant.
(Product name: Toho Chemical Industry Co., Ltd.) Mix 5 fff parts &
After pulverizing, add water and stir evenly to make a powder with a diameter of 0゜7r.
After extrusion through n rn sieve holes and drying, the mixture was cut into lengths of 1 to 2 mm to obtain 10% granules.
実施例6 茎葉処理試験
20cmX20cmの樹脂性ポットに畑土壌を詰め、コ
ムギ、トウモロコシ、ダイズ等の作物の種子と、表3に
示す雑位の種子を播き、これらが見えなくなる程度に覆
土した。ノビエが1.5〜2.0菓明になった時に、前
記実施例4に準じて製剤した本発明化合物の水相剤の所
定薬量をボットあたり20m1の水で希釈して均一に散
布した。その後温室内に静置して、薬剤処理後3日間は
茎葉部への散水はさけ、その後は適時散水した。薬剤散
布後14 [I 11に雑草および作物の生育状態を観
察し、表7に示す結果を7++た。Example 6 Stalk Treatment Test A 20 cm x 20 cm resinous pot was filled with field soil, and seeds of crops such as wheat, corn, and soybean, as well as seeds of the miscellaneous positions shown in Table 3, were sown, and the pots were covered with soil to the extent that they were no longer visible. When the number of wild animals reached 1.5 to 2.0, a predetermined amount of the aqueous phase agent of the compound of the present invention prepared according to Example 4 was diluted with 20 ml of water per bot and uniformly sprayed. . Thereafter, the plants were left in a greenhouse, and the stems and leaves were not watered for 3 days after the chemical treatment, and then watered at appropriate times. The growth conditions of weeds and crops were observed at 11 days after the chemical spraying, and the results shown in Table 7 were 7++.
除つ効果の評価は下記のように0〜5の数字で表わした
。また、作物に対する薬害も除ヴ効果と同じ基べへで示
した。The evaluation of the removal effect was expressed as a number from 0 to 5 as shown below. In addition, chemical damage to crops was also shown on the same basis as the extermination effect.
0− ・抑φ率 0〜9%
1 ・抑つ率 10〜29%
2・ ・抑[有]率 30〜49%
゛3・ ・抑苧率 50〜69%
4# ・抑顕率 70〜89%
5・ ・抑苧率 90〜100%
実施例7 移植水稲における土壌処理試験100 cm
2のプラスチックポットに代掻き状態の水111土壌を
詰め、表4に示す雑草の種子を播き、さらに2菓明の水
稲(品種ニャマホウシ)を1ポット当り2本2体を移植
し、約2cmの湛水状態で情理した。表8に示す雑ビ〆
の発生初期に前記実施例4に塾じて製剤した本発明化合
物の水和剤の所定(Jltj ILLをポットあたり1
0m1の水で希釈して水面に滴ド処理した。その後温室
内に静置し、適時散水した。薬剤処理後20日0に除菫
効果および薬害を調査し、表8に示す結果を得た。0- ・Suppression rate 0~9% 1 ・Suppression rate 10~29% 2. ・Suppression rate 30~49% ゛3. ・Suppression rate 50~69% 4# ・Suppression rate 70~ 89% 5. - Ramie suppression rate 90-100% Example 7 Soil treatment test on transplanted paddy rice 100 cm
Fill the plastic pots No. 2 with 111 water and soil in a puddling state, sow the seeds of the weeds shown in Table 4, and transplant two paddy rice plants (variety Nyamahoushi) into each pot to a depth of about 2 cm. I felt emotional in a water state. At the early stage of the development of miscellaneous dirt shown in Table 8, a prescribed amount of the hydrating agent (Jltj ILL) of the compound of the present invention prepared according to Example 4 was added per pot.
It was diluted with 0ml of water and applied dropwise to the water surface. The plants were then placed in a greenhouse and watered at appropriate times. The violet removal effect and drug damage were investigated on day 20 after the chemical treatment, and the results shown in Table 8 were obtained.
除f:+:効果の評価および薬害の評価は実施例6と同
様に行なった。Exclusion f:+: Evaluation of efficacy and evaluation of drug damage were performed in the same manner as in Example 6.
Claims (2)
示し、Y^1、Y^2は同一でも異なっていてもよい。 R^1は水素原子またはC_1−C_6アルキル基を示
し、R^2はC_1−C_6アルキルチオ基またはC_
1−C_6アルコキシ基を示し、AはNR^3R^4(
ただし、R^3、R^4は水素原子、C_1−C_6ア
ルキル基、C_1−C_6アルキルチオ基、C_1−C
_6アルコキシ基、C_1−C_6アルケニル基または
アリール基を示し、R^3、R^4は同一でも異なって
いてもよい。)、▲数式、化学式、表等があります▼(
ただし、 lは1〜10の整数を示す。)または ▲数式、化学式、表等があります▼ (ただし、Y^3は酸素原子または硫黄原子を示し、m
、nは1〜10の整数を示す。)を示す。}で示される
ウレイドカーバメート誘導体。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [I] {However, Y^1 and Y^2 represent oxygen atoms or sulfur atoms, and Y^1 and Y^2 may be the same. May be different. R^1 represents a hydrogen atom or a C_1-C_6 alkyl group, and R^2 represents a C_1-C_6 alkylthio group or C_
1-C_6 alkoxy group, A is NR^3R^4(
However, R^3 and R^4 are hydrogen atoms, C_1-C_6 alkyl group, C_1-C_6 alkylthio group, C_1-C
It represents a _6 alkoxy group, a C_1-C_6 alkenyl group, or an aryl group, and R^3 and R^4 may be the same or different. ), ▲Mathematical formulas, chemical formulas, tables, etc.▼(
However, l represents an integer from 1 to 10. ) or ▲Mathematical formulas, chemical formulas, tables, etc.▼ (However, Y^3 represents an oxygen atom or a sulfur atom, and m
, n represents an integer of 1 to 10. ) is shown. } A ureido carbamate derivative represented by.
されるウレイドカーバメート誘導体を有効成分として含
有する除草剤。(2) A herbicide containing a ureidocarbamate derivative represented by the general formula [I] as set forth in claim 1 as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30615388A JPH02152964A (en) | 1988-12-05 | 1988-12-05 | Ureidocarbamate derivative and herbicide containing the same as active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30615388A JPH02152964A (en) | 1988-12-05 | 1988-12-05 | Ureidocarbamate derivative and herbicide containing the same as active ingredient |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH02152964A true JPH02152964A (en) | 1990-06-12 |
Family
ID=17953689
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP30615388A Pending JPH02152964A (en) | 1988-12-05 | 1988-12-05 | Ureidocarbamate derivative and herbicide containing the same as active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH02152964A (en) |
-
1988
- 1988-12-05 JP JP30615388A patent/JPH02152964A/en active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JPS62174059A (en) | Pyrimidine derivative and herbicide | |
JPS6134425B2 (en) | ||
JPH0435462B2 (en) | ||
JPS60166665A (en) | Tetrahydro-2h-indazole derivative, preparation thereof and herbicide containing same as active constituent | |
JPH035454A (en) | Novel n-phenylpyrrolidines | |
JPH02152964A (en) | Ureidocarbamate derivative and herbicide containing the same as active ingredient | |
JPS5844643B2 (en) | Shinkinadjiyosouzai | |
JPH02142771A (en) | Biscarbamate derivative and herbicide containing thereof as active ingredient | |
JPS61210003A (en) | Herbicide | |
JPS59216874A (en) | Carbamate derivative | |
JPS6229433B2 (en) | ||
JPS62267274A (en) | 1,2,4-oxadiazole derivative | |
JPH02108667A (en) | Ureido carbamate derivative and herbicide containing the derivative as active ingredient | |
JPH02152965A (en) | Biscarbamate derivative and herbicide containing the same as active ingredient | |
JPS591697B2 (en) | Method for producing cyclohexane derivatives | |
JPS6237035B2 (en) | ||
JPH04330059A (en) | Carbamate derivative and herbicide containing the same as active ingredient | |
JPS625431B2 (en) | ||
JPS5936896B2 (en) | α-acetyl cinnamic acid ester derivatives, their production methods, and herbicides comprising the compounds | |
JPS603300B2 (en) | Imidazole derivatives and insecticides and acaricides | |
JPH08193007A (en) | Herbicide composition for paddy field | |
JPS63264584A (en) | Herbicidal composition | |
JPS6130671B2 (en) | ||
JPS6055502B2 (en) | Metaphenoxybenzoic acid amide derivatives, their production methods, and herbicides containing them as active ingredients | |
JPH0434538B2 (en) |