JP2004534096A - 除草活性を有する新規な置換アニリン誘導体 - Google Patents
除草活性を有する新規な置換アニリン誘導体 Download PDFInfo
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- JP2004534096A JP2004534096A JP2003512194A JP2003512194A JP2004534096A JP 2004534096 A JP2004534096 A JP 2004534096A JP 2003512194 A JP2003512194 A JP 2003512194A JP 2003512194 A JP2003512194 A JP 2003512194A JP 2004534096 A JP2004534096 A JP 2004534096A
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- JP
- Japan
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- group
- general formula
- alkyl group
- halogen atom
- haloalkyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 11
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 25
- 125000005843 halogen group Chemical group 0.000 claims abstract description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 241000196324 Embryophyta Species 0.000 claims description 14
- 239000004009 herbicide Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- -1 phenoxy, phenoxymethyl Chemical group 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 4
- 240000008867 Capsella bursa-pastoris Species 0.000 description 4
- 240000006122 Chenopodium album Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NEKOXWSIMFDGMA-UHFFFAOYSA-N Isopropalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(C)C)C=C1[N+]([O-])=O NEKOXWSIMFDGMA-UHFFFAOYSA-N 0.000 description 4
- 235000007846 Papaver rhoeas Nutrition 0.000 description 4
- 240000004674 Papaver rhoeas Species 0.000 description 4
- 244000234609 Portulaca oleracea Species 0.000 description 4
- 235000001855 Portulaca oleracea Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000001448 anilines Chemical class 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 4
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 4
- 241001621841 Alopecurus myosuroides Species 0.000 description 3
- 235000009344 Chenopodium album Nutrition 0.000 description 3
- DHWRNDJOGMTCPB-UHFFFAOYSA-N Dimefuron Chemical compound ClC1=CC(NC(=O)N(C)C)=CC=C1N1C(=O)OC(C(C)(C)C)=N1 DHWRNDJOGMTCPB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000042664 Matricaria chamomilla Species 0.000 description 3
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000062793 Sorghum vulgare Species 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 230000035784 germination Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MPPOHAUSNPTFAJ-SECBINFHSA-N (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-SECBINFHSA-N 0.000 description 2
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 2
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 2
- 0 *C(*)(*)c1ccc(*)c(*)c1* Chemical compound *C(*)(*)c1ccc(*)c(*)c1* 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- MVHWKYHDYCGNQN-UHFFFAOYSA-N 1,5-dichloro-3-fluoro-2-(4-nitrophenoxy)benzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=C(F)C=C(Cl)C=C1Cl MVHWKYHDYCGNQN-UHFFFAOYSA-N 0.000 description 2
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- BXKKQFGRMSOANI-UHFFFAOYSA-N 1-methoxy-3-[4-[(2-methoxy-2,4,4-trimethyl-3h-chromen-7-yl)oxy]phenyl]-1-methylurea Chemical compound C1=CC(NC(=O)N(C)OC)=CC=C1OC1=CC=C2C(C)(C)CC(C)(OC)OC2=C1 BXKKQFGRMSOANI-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 description 2
- KFEFNHNXZQYTEW-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methylbenzoic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=CC(C)=CC=C1C(O)=O KFEFNHNXZQYTEW-UHFFFAOYSA-N 0.000 description 2
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 2
- GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 2
- YUVKUEAFAVKILW-UHFFFAOYSA-N 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 YUVKUEAFAVKILW-UHFFFAOYSA-N 0.000 description 2
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 2
- HCNBYBFTNHEQQJ-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(N=2)C(F)(F)F)C(O)=O)=N1 HCNBYBFTNHEQQJ-UHFFFAOYSA-N 0.000 description 2
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- IOYNQIMAUDJVEI-ZFNPBRLTSA-N 2-[N-[(E)-3-chloroprop-2-enoxy]-C-ethylcarbonimidoyl]-3-hydroxy-5-(oxan-4-yl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOC\C=C\Cl)CC)=C(O)CC1C1CCOCC1 IOYNQIMAUDJVEI-ZFNPBRLTSA-N 0.000 description 2
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- ADZSGNDOZREKJK-UHFFFAOYSA-N 4-amino-6-tert-butyl-3-ethylsulfanyl-1,2,4-triazin-5-one Chemical compound CCSC1=NN=C(C(C)(C)C)C(=O)N1N ADZSGNDOZREKJK-UHFFFAOYSA-N 0.000 description 2
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- KCOCSOWTADCKOL-UHFFFAOYSA-N Ethidimuron Chemical compound CCS(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 KCOCSOWTADCKOL-UHFFFAOYSA-N 0.000 description 2
- 239000005513 Fenoxaprop-P Substances 0.000 description 2
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- KABSXJFKDZOTFH-UHFFFAOYSA-N methyl 5-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]-1-pyridin-2-ylpyrazole-4-carboxylate Chemical compound COC(=O)C=1C=NN(C=2N=CC=CC=2)C=1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 KABSXJFKDZOTFH-UHFFFAOYSA-N 0.000 description 1
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 239000002480 mineral oil Chemical class 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- FIEZAOQZGZYEKV-UHFFFAOYSA-N n-(2-hydroxy-4-methylphenyl)cyclopropanecarboxamide Chemical compound OC1=CC(C)=CC=C1NC(=O)C1CC1 FIEZAOQZGZYEKV-UHFFFAOYSA-N 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- HZDIJTXDRLNTIS-DAXSKMNVSA-N n-[[(z)-but-2-enoxy]methyl]-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(COC\C=C/C)C(=O)CCl HZDIJTXDRLNTIS-DAXSKMNVSA-N 0.000 description 1
- JXTHEWSKYLZVJC-UHFFFAOYSA-N naptalam Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC2=CC=CC=C12 JXTHEWSKYLZVJC-UHFFFAOYSA-N 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- LLLFASISUZUJEQ-UHFFFAOYSA-N orbencarb Chemical compound CCN(CC)C(=O)SCC1=CC=CC=C1Cl LLLFASISUZUJEQ-UHFFFAOYSA-N 0.000 description 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- CSWIKHNSBZVWNQ-UHFFFAOYSA-N pethoxamide Chemical compound CCOCCN(C(=O)CCl)C(=C(C)C)C1=CC=CC=C1 CSWIKHNSBZVWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000003408 phase transfer catalysis Methods 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 1
- ASRAWSBMDXVNLX-UHFFFAOYSA-N pyrazolynate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OS(=O)(=O)C1=CC=C(C)C=C1 ASRAWSBMDXVNLX-UHFFFAOYSA-N 0.000 description 1
- FKERUJTUOYLBKB-UHFFFAOYSA-N pyrazoxyfen Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=O)C=1C(C)=NN(C)C=1OCC(=O)C1=CC=CC=C1 FKERUJTUOYLBKB-UHFFFAOYSA-N 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 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
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/60—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
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- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C275/36—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with at least one of the oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. N-aryloxyphenylureas
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- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
本発明は、新規な置換アニリン誘導体に関する。
更に詳細には、本発明は、除草活性の高い新規なオルト置換アニリン誘導体、その調製方法及び農業作物における雑草を防除する除草剤としての使用に関する。
ドイツ特許出願第2,855,699号には、除草活性を有するメタ置換アニリン誘導体が記載されている。しかしながら、これらの化合物は、高い施用量を必要とする点で除草剤として適当でないと思われる。
国際出願第98/03500号には、アミン基について“オルト”位に、種々に置換されたフェノキシ基、フェノキシメチル基又はフェニルメトキシ基で置換されたヘテロシクリル又はフェニルカルボキシアニリドが記載されている。上記特許出願の生成物は、実質的に殺真菌剤や殺虫剤として活性である。
そこで、本出願人は、これに対して、アミン基について“オルト”位に、特定の分類によって置換されたフェノキシメチル基、フェニルメトキシ基又はフェノキシ基で置換された一連の新規なアニリン誘導体が、驚くべきことに高除草活性を有し、農地対象の1種以上の栽培に対する低薬害を合わせもっていることを見出した。
従って、本発明の目的は、下記一般式(I)を有する新規な化合物に関する。
【0002】
【化1】
【0003】
(式中、Rは水素原子、C1-C8アルキル基又はハロアルキル基、C2-C8アルコキシアルキル基又はハロアルコキシアルキル基、C2-C8アルケニル基又はハロアルケニル基、C2-C8アルキニル基又はハロアルキニル基、ハロゲン原子及び/又はC1-C4アルキル基又はハロアルキル基で置換されていてもよいC3-C8シクロアルキル基又はC4-C9シクロアルキルアルキル基、C1-C8アルコキシル基又はハロアルコキシル基、NRaRb基であり、
RaとRbは同じか又は異なる、水素原子; C1-C8アルキル基; ハロゲン原子、CN基、NO2基、C1-C4アルキル基、ハロアルキル基、アルコキシル基、ハロアルコキシル基で置換されていてもよいフェニル基又はベンジル基であり; 又はRaとRbが結合して酸素原子で中断されていてもよいC2-C8アルキレン鎖でもあり、
Rnは水素原子、又はC1-C4アルキル基又はハロアルキル基であり、
R1は水素原子、ハロゲン原子、C1-C4アルキル基又はハロアルキル基、C1-C4アルコキシル基又はハロアルコキシル基、C1-C4アルキルチオ基又はハロアルキルチオ基、シアノ基、ニトロ基であり、
R2はC1-C4アルキル基、ハロアルキル基、アルコキシル基、ハロアルコキシル基、アルキルチオ基又はハロアルキルチオ基、又はハロゲン原子であり、
XとX1は同じか又は異なる、水素原子又はハロゲン原子であり、
Aは酸素原子、-CR3R4O-基、-OCR3R4-基であり、ここで、R3とR4は同じか又は異なる、水素原子又はC1-C4アルキル基、ハロアルキル基である。)
活性が興味深い一般式(I)を有する化合物の個々の例を下記表1に明記する。
【0004】
【表1】
【0005】
【表2】
【0006】
本発明の目的は、更に、一般式(I)を有する化合物の調製方法に関する。
一般式(I)を有する化合物は、一般式(II)を有するアミン誘導体と一般式(III)を有する化合物とを下記スキーム1に従って反応させることにより調製することができる。
スキーム1
【0007】
【化2】
【0008】
前記式においては、R、Rn、R1、R2、X、X1、Aは上記意味を有し、Zはハロゲン原子、アルコキシル基、ヒドロキシル基である。
上記方法を行う反応条件は、式(III)を有する化合物の種類に関して変えることができる。
例えば、Zがハロゲン原子である場合、反応は不活性溶媒の存在下と有機塩基と無機塩基の存在下に-20℃から反応混合物の沸点までの範囲にある温度で行うことが好ましい。
上記反応に使用し得る溶媒の例としては、脂肪族炭化水素又は脂環式炭化水素(石油エーテル、ヘキサン、シクロヘキサン等)、塩素化炭化水素(塩化メチレン、クロロホルム、四塩化炭素、ジクロロエタン等)、芳香族炭化水素(ベンゼン、トルエン、キシレン、クロロベンゼン等)、エーテル(ジエチルエーテル、ジイソプロピルエーテル、ジメトキシエタン、ジオキサン、テトラヒドロフラン等)、エステル(酢酸エチル等)、ケトン(アセトン、メチルエチルケトン、メチルプロピルケトン、メチルイソブチルケトン等)、ニトリル(アセトニトリル、ベンゾニトリル等)、非プロトン性双極性溶媒(ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルホスホロトリアミド、ジメチルスルホキシド、スルホン、N-メチルピロリドン等)が挙げられる。
上記反応に使用し得る無機塩基は、例えば、水酸化物、炭酸ナトリウムや重炭酸ナトリウム、炭酸カリウムや重炭酸カリウムである。
上記反応に使用し得る有機塩基は、例えば、トリエチルアミン、ピリジン、4-N,N-ジメチルアミノピリジン、N,N-ジメチルアニリン、N-メチルピペリジン、ルチジン、ジアザビシクロオクタン(DABCO)、ジアザビシクロノネン(DBN)、ジアザビシクロウンデセン(DBU)である。
また、Aが-CR3R4O-基である一般式(I)を有する化合物は、一般式(IV)を有する誘導体と一般式(V)を有するフェノールとを下記スキーム2に従って縮合させて一般式(Ia)を有するエーテルを得ることにより調製することができる。
スキーム2
【0009】
【化3】
【0010】
この反応スキームにおいて明記された一般式においては、R、Rn、R1、R2、R3、R4、X、X1は上で定義した意味を有し、Z1はハロゲン原子、好ましくは塩素又は臭素、又はRzSO3基であり、ここで、RzはC1-C4アルキル基又はC1-C4アルキル基で置換されていてもよいフェニル基である。
エーテル化反応は、1種以上の不活性有機溶媒と塩基の存在下に-10℃から反応混合物の沸点までの範囲にある温度で行われることが好ましい。
上記反応に使用し得る有機溶媒は、例えば、芳香族炭化水素(ベンゼン、トルエン、キシレン、クロロベンゼン等)、エーテル(ジエチルエーテル、ジイソプロピルエーテル、ジメトキシエタン、ジオキサン、テトラヒドロフラン等)、アルコールやグリコール(メタノール、エタノール、メチセロソルブ、エチレングリコール等)、ケトン(アセトン、メチルエチルケトン、メチルプロピルケトン、メチルイソブチルケトン等)、ニトリル(アセトニトリル、ベンゾニトリル等)、非プロトン性双極性溶媒(ジメチルホルムアミド、ジメチルアセトアミド、ヘキサメチルホスホロトリアミド、ジメチルスルホキシド、スルホラン、N-メチルピロリドン等)である。
上記反応に用いられる無機塩基は、例えば、水素化ナトリウム又は水素化カリウム、水酸化ナトリウム又は水酸化カリウム、炭酸ナトリウム又は炭酸カリウムである。
反応は、有利には、溶媒として水と水と混じらない有機溶媒を用いる二相系で、Dehmlow & Dehmlow, “Phase Transfer Catalysis”(1983), Verlag Chemieに記載されている相転移触媒の存在下に行うことができる。
同様に、一般式(I)(式中、Aは-OCR3R4-基である。)を有する化合物は、一般式(VI)を有するフェノールと一般式(VII)を有する誘導体とを下記反応スキーム3に従って反応させて一般式(Ib)を有するエーテルを得ることにより調製することができる。
スキーム3
【0011】
【化4】
【0012】
この反応スキームに明記された一般式においては、R、Rn、R1、R2、R3、R4、X、X1は上で定義した意味を有し、Z2はハロゲン原子、好ましくは塩素又は臭素、又はRzSO3基であり、ここで、RzはC1-C4アルキル基又はC1-C4アルキル基で置換されていてもよいフェニル基である。
操作手順と、スキーム3で定義したエーテル化反応に使用し得る溶媒と塩基の種類は、スキーム2の反応に指定されたものと全く同じである。
一般式(II)、(III)、(IV)、(V)、(VI)、(VII)を有する中間体は、それ自体がまだ知られていない場合、有機化学の実験において既知の方法に従って容易に調製することができる。
既に述べたように、一般式(I)を有する化合物は、有用な作物を雑草から保護するために農耕地での使用に適する除草活性が高い。
特に本発明の目的の化合物は、多くの単子葉植物や双子葉植物の発芽前と発芽後双方の防除に有効である。同時に、これらの化合物は、発芽前及び/又は発芽後の処理に用いられる作物について適合性を示し、毒性作用もない。
一般式(I)を有する化合物を用いて効果的に防除し得る雑草の例は、イチビ(Abutilon theophrasti)、サジオモダカ(Alisma plantago)、アマランサス属(Amaranthus spp.)、アムニ・マイウス(Amni maius)、ナズナ(Capsella bursa pastoris)、シロザ(Chenopodium album)、シロバナヒルガオ(Convolvulus sepium)、ヤエムグラ(Galium aparine)、イタヤカエデ(Geranium dissectum)、イポメア属(Ipomea spp.)、シカギク属(Matricaria spp.)、グビジンソウ(Papaver rhoeas)、リョクトウ(Phaseolus aureus)、ハルタデ(Polygonum persicaria)、ハナスベリヒユ(Portulaca oleracea)、アメリカキンゴジカ(Sida spinosa)、ノハラガラシ(Sinapis arvensis)、イヌホウズキ(Solanum nigrum)、ウシハコベ(Stellaria media)、イヌノフグリ属(Veronica spp.)、スミレ属(Viola spp.)、オナモミ属(Xanthium spp.)、ノスズメノテッポウ(Alopecurus myosuroides)、カラスムギ(Avena fatua)、カヤツリグサ属(Cyperus spp.)、ディジタリア・サンギナリス(Digitaria sanguinalis)、イヌビエ属(Echinocloa spp.)、ヘレノカリス・アビクラリス(Heleocharis avicularis)、ヘテランテラ属(Heteranthera spp.)、キビ属(Panicum spp.)、イチゴツナギ属(Poa spp.)、アブラガヤ属(Scirpus spp.)、モロコシ属(Sorghum spp.)等である。
農地に用いられる施用量においては、上記化合物はイネ(Oryza sativa)、コムギ(Triticum sp.)、オオムギ(Hordeum vulgare)、トウモロコシ(Zea mays)、ダイズ(Glycine max)のような重要な農作物のいずれに対しても毒性作用を示さない。
【0013】
本発明の目的は、更に、一般式(I)を有する化合物の施用によって耕作面積における雑草を防除する方法に関する。
所望の効果を得るために施用される化合物の量は、使用化合物、保護すべき作物、駆除すべき雑草、被害の程度、気候条件、土地の特徴、施用法等の種々の要因に関して変えることができる。
一般的には1ヘクタール当たり1g〜1000gの範囲にある化合物の施用量によって十分に防除される。
農業に使用する場合、活性物質として一般式(I)を有する1種以上の化合物を、おそらく異性体の混合物としても含有する除草活性を有する組成物を用いることがしばしば有利である。
組成物は、乾燥粉末、水和性粉末、乳化できる濃縮物、ミクロエマルジョン、ペースト、顆粒、溶液、懸濁液等の形で用いることができ、組成物の種類の選択は個々の使用に左右される。
本組成物は、既知の方法に従って、例えば、活性物質を溶媒及び/又は固体希釈媒体で、場合によっては界面活性剤の存在下に希釈又は溶解することにより調製される。
固体不活性希釈剤、又は担体として、カオリン、アルミナ、シリカ、タルク、ベントナイト、チョーク、石英、ドロマイト、アタパルガイト、モンモリロナイト、ケイソウ土、セルロース、デンプン等が使用し得る。
液体不活性希釈剤として、水、又は有機溶媒、例えば、芳香族炭化水素(キシロール、アルキルベンゾールの混合物等)、脂肪族炭化水素(ヘキサン、シクロヘキサン等)、ハロゲン化芳香族炭化水素(クロロベンゾール等)、アルコール(メタノール、プロパノール、ブタノール、オクタノール等)、エステル(酢酸イソブチル等)、ケトン(アセトン、シクロヘキサノン、アセトフェノン、イソホロン、エチルアミルケトン等)、又は植物油又は鉱油又はその混合物等が使用し得る。
界面活性剤として、非イオン型(ポリエトキシル化アルキルフェノール、ポリエトキシル化脂肪アルコール等)、アニオン型(アルキルベンゼンスルホン酸塩、アルキルスルホン酸塩等)、カチオン型(第四級アルキルアンモニウム塩等)の湿潤剤や乳化剤が使用し得る。
分散剤(例えば、リグニンやその塩、セルロース誘導体、アルギン酸塩等)、安定剤(例えば、抗酸化剤、紫外線吸収剤等)も添加し得る。
上記組成物の作用範囲を広くするために、例えば、他の除草剤、殺真菌剤、殺虫剤、ダニ駆除剤、肥料のような他の活性成分を添加することが可能である。
【0014】
一般式(I)を有する1種以上の化合物を含有する組成物に添加し得る他の除草剤の例は次のものである。
アセトクロル(acetochlor)、アシフルオルフェン(acifluorfen)、アクロニフェン(aclonifen)、AKH-7088、アラクロル(alachlor)、アロキシジム(alloxydim)、アメトリン(ametryn)、アミカルバゾン(amicarbgazone)、アミドスルフロン(amidosulfuron)、アミトロール(amitrole)、アニロフォス(anilofos)、アスラム(asulam)、アトラジン(atrazine)、アザフェニジン(azafenidin)、アジムスルフロン(azimsulfuron)、アジプロトリン(aziprotryne)、BAY MKH 6561、ベフルブトアミド(beflubutamid)、ベナゾリン(benazolin)、ベンフルラリン(benfluralin)、ベンフレセート(benfuresate)、ベンスルフロン(bensulfuron)、ベンスリド(bensulide)、ベンタゾン(bentazone)、ベンズフェンジゾン(benzfendizone)、ベンゾビシクロン(benzobicyclon)、ベンゾフェナップ(benzofenap)、ベンズチアズロン(benzthiazuron)、ビフェノックス(bifenox)、ビラナフォス(bilanafos)、ビスピリバックナトリウム(bispyribac-sodium)、ブロマシル(bromacil)、ブロモブチド(bromobutide)、ブロモフェノキシム(bromofenoxim)、ブロモキシニル(bromoxynil)、ブタクロル(butachlor)、ブタフェナシル(butafenacil)、ブタミフォス(butamifos)、ブテナクロル(butenachlor)、ブトリラリン(butralin)、ブトロキシジム(butroxydim)、ブチレート(butylate)、カフェンストロール(cafenstrole)、カルベトアミド(carbetamide)、カルフェントラゾンエチル(carfentrazone-ethyl)、クロメトキシフェン(chlomethoxyfen)、クロルアンベン(chloramben)、クロルブロムロン(chlorbromuron)、クロルブファム(chlorbufam)、クロルフルレノール(chlorflurenol)、クロルイダゾン(chloridazon)、クロルイムロン(chlorimuron)、クロルニトロフェン(chlornitrofen)、クロロトルロン(chlorotoluron)、クロロキシウロン(chloroxuron)、クロルプロファム(chlorpropham)、クロルスルフロン(chlorsulfuron)、クロルタール(chlorthal)、クロルチアミド(chlorthiamid)、シニドンエチル(cinidon ethyl)、シンメチリン(cinmethylin)、シノスルフロン(cinosulfuron)、クレトジム(clethodim)、クロジナフォプ(clodinafop)、クロマゾン(clomazone)、クロメプロプ(clomeprop)、クロピラリド(clopyralid)、クロランスラムメチル(cloransulam-methyl)、クミルウロン(cumyluron)(JC-940)、シアナジン(cyanazine)、シクロエート(cycloate)、シクロスルファムロン(cyclosulfamuron)、シクロキシジム(cycloxydim)、シハロフォプブチル(cyhalofop-butyl)、2,4-D、2,4-DB、ダイムロン(daimuron)、ダラポン(dalapon)、デスメジファム(desmedipham)、デスメトリン(desmetryn)、ジカンバ(dicamba)、ジクロベニル(dichlobenil)、ジクロルプロプ(dichlorprop)、ジクロルプロプ-P(dichlorprop-P)、
【0015】
ジクロフォプ(diclofop)、ジクロスラム(diclosulam)、ジエタチル(diethatyl)、ジフェノキシウロン(difenoxuron)、ジフェンゾクアート(difenzoquat)、ジフルフェニカン(diflufenican)、ジフルフェンゾピル(diflufenzopyr)、ジメフロン(dimefuron)、ジメピペレート(dimepiperate)、ジメタクロル(dimethachlor)、ジメタメトリン(dimethametryn)、ジメテンアミド(dimethenamid)、ジニトルアミン(dinitramine)、ジノセブ(dinoseb)、ジノセブアセテート(dinoseb acetate)、ジノテルブ(dinoterb)、ジフェンアミド(diphenamid)、ジプロペトリン(dipropetryn)、ジクアート(diquat)、ジチオピル(dithiopyr)、1-ジウロン(1-diuron)、エグリナジン(eglinazine)、エンドタール(endothal)、EPTC、エスプロカルブ(esprocarb)、エタルフルラリン(ethalfluralin)、エタメトスルフロンメチル(ethametsulfuron-methyl)、エチジムロン(ethidimuron)、エチオジン(ethiozin)(SMY 1500)、エトフメセート(ethofumesate)、エトキシフェンエチル(ethoxyfen-ethyl)(HC-252)、エトキシスルフロン(ethoxysulfuron)、エトベンズアニド(etobenzanid)(HW 52)、フェノキサプロプ(fenoxaprop)、フェノキサプロプ-P(fenoxaprop-P)、フェントラズアミド(fentrazamide)、フェンウロン(fenuron)、フラムプロプ(flamprop)、フラムプロプ-M(flamprop-M)、フラザスルフロン(flazasulfuron)、フロラスラム(florasulam)、フルアジフォプ(fluazifop)、フルアジフォプ-P(fluazifop-P)、フルアゾレート(fluazolate)(JV 485)、フルカルバゾンナトリウム(flucarbazone-sodium)、フルクロラリン(fluchloralin)、フルフェナセト(flufenacet)、フルメツラム(flumetsulam)、フルミクロラクペンチル(fulumiclorac-pentyl)、フルミオキサジン(flumioxazin)、フルミプロピン(flumipropin)、フルオメツロン(fluometuron)、フルオログリコフェン(fluoroglycofen)、フルオロニトロフェン(fluoronitrofen)、フルポキサム(flupoxam)、フルプロパネート(flupropanate)、フルピルスルフロン(flupyrsulfuron)、フルレノール(flurenol)、フルリドン(fluridone)、フルロクロリドン(flurochloridone)、フルロキシピル(flupyrsulfuron)、フルルタモン(flurtamone)、フルチアセトメチル(fluthiacet-methyl)、ホメサフェン(fomesafen)、ホラムスルフロン(foramsuluron)、ホスアミン(fosamine)、フリルオキシフェン(furyloxyfen)、グルホシネート(glufosinate)、
【0016】
グリホセート(glyphosate)、ハロスルフロンメチル(halosulfuron-methyl)、ハロキシフォプ(haloxyfop)、ハロキシフォプ-Pメチル(haloxyfop-P-methyl)、ヘキサジノン(hexazinone)、イマザメタベンズ(imazamethabenz)、イマザモックス(imazamox)、イマザピック(imazapic)、イマザピル(imazapyr)、イマザキン(imazaquin)、イマゼタピル(imazethapyr)、イマゾスルフロン(imazosulfuron)、イマダノファン(indanofan)、ヨードスルフロン(iodosulfuron)、イオキシニル(ioxynil)、イソプロパリン(isopropalin)、イソプロツロン(isoproturon)、イソウロン(isouron)、イソキサベン(isoxaben)、イソキサクロルトール(isoxachlortole)、イソキサフルトール(isoxaflutole)、イソキサピリフォプ(isoxapyrifop)、KPP-421、ラクトフェン(lactofen)、レナシル(lenacil)、リヌロン(linuron)、LS830556、MCPA、MCPAチオエチル(MCPA-thioethyl)、MCPB、メコプロプ(mecoprop)、メコプロプ-P(mecoprop-P)、メフェナセト(mefenacet)、メソトリオン(mesotrione)、メタミトロン(metamitron)、メタザクロル(metazachlor)、メタベンズチアズロン(methabenzthiazuron)、メタゾール(methazole)、メトプロトリン(methoprotryne)、メチルディムロン(methyldymron)、メトベンズロン(metobenzuron)、メトブロムロン(metobromuron)、メトラクロル(metolachlor)、S-メトラクロル(S-metolachlor)、メトスラム(metosulam)、メトキシウロン(metoxuron)、メトリブジン(metribuzin)、メツルフロン(metsulfuron)、モリネート(molinate)、モナリド(monalide)、モノリヌロン(monolinuron)、ナプロアニリド(naproanilide)、ナプロプアミド(napropamide)、ナプタラム(naptalam)、NC-330、ネブロン(neburon)、ニコスルフロン(nicosulfuron)、ニピラクロフェン(nipyraclofen)、ノルフルラゾン(norflurazon)、オルベンカルブ(orbencarb)、オリザリン(oryzalin)、オキサジアルギル(oxadiargyl)、オキサジアゾン(oxadiazon)、オキサスルフロン(oxasulfuron)、オキサジクロメホン(oxaziclomefene)、オキシフルオルフェン(oxyfluorfen)、パラクアート(paraquat)、ペ
【0017】
ブレート(pebulate)、ペンジメタリン(pendimethalin)、ペンタノクロル(pentanochlor)、ペントキサゾン(pentoxazone)、ペントキシアミド(pethoxamid)、フェンメジファム(phenmedipham)、ピクロラム(picloram)、ピコリナフェン(picolinafen)、ピペロホス(piperophos)、プレチラクロル(pretilachlor)、プリミスルフロン(primisulfuron)、プロジアミン(prodiamine)、プロフルアゾール(profluazol)、プログリナジン(proglinazine)、プロメトン(prometon)、プロメトリン(prometryne)、プロパクロル(propachlor)、プロパニル(propanil)、プロパキザフォプ(propaquizafop)、プロパジン(propazine)、プロファム(propham)、プロピソクロル(propisochlor)、プロピズアミド(propyzamide)、プロスルフォカルブ(prosulfocarb)、プロスルフロン(prosulfuron)、ピラクロニル(pyraclonil)、ピラフルフェンエチル(pyraflufen-ethyl)、ピラゾリネート(pyrazolynate)、ピラゾスルフロン(pyrazosulfuron)、ピラゾキシフェン(pyrazoxyfen)、ピリベンゾキシム(pyribenzoxim)、ピリブチカルブ(pyributicarb)、ピリダフォル(pyridafol)、ピリデート(pyridate)、ピリフタリド(pyriftalid)、ピリミノバックメチル(pyriminobac-methyl)、ピリチオバックナトリウム(pyrithobac-sodium)、キンクロラック(quinclorac)、キンメラック(quinmerac)、キザロフォップ(quizalofop)、キザロフォップ-P(quizalofop-P)、リムスルフロン(rimsulfuron)、セトキシジム(sethoxydim)、シズロン(siduron)、シマジン(simazine)、シメトリン(simetryn)、スルコトリオン(sulcotrione)、スルフェントラゾン(sulfentrazone)、スルフォメツロンメチル(sulfometuron-methyl)、スルフォスルフロン(sulfosulfuron)、2,3,6-TBA、TCAナトリウム(TCA-sodium)、テブタム(tebutam)、テブチウロン(tebuthiuron)、テプラロキシジム(tepraloxydim)、テルバシル(terbacil)、テルブメトン(terbumeton)、テルブチルアジン(terbuthyl-azine)、テルブトリン(terbutryn)、テニルクロル(thenylchlor)、チアザフルロン(thiazafluron)、チアゾピル(thiazopyr)、チジアジミン(thiadiazimin)、チフェンスルフロンメチル(thifensulfuron-methyl)、チオベンカルブ(thiobencarb)、チオカルバジル(tiocarbazil)、チオクロリム(tioclorim)、トラルコキシジム(tralkoxydim)、トリアルレート(tri-allate)、トリアスルフロン(triasulfuron)、トリアジフラム(triaziflam)、トリベヌロン(tribenuron)、トリクロピル(triclopyr)、トリエタジン(trietazine)、トリフロキシスルフロン(trifloxysulfuron)、トリフルラリン(trifluralin)、トリフルスルフロンメチル(triflusulfuron)、トリトスルフロン(tritosulfuron)、UBI-C4874、ベルノレート(vernolate)。
上記組成物中の活性物質の濃度は、広範囲に変動させることができ、活性化合物、予定されている施用、環境条件、使用製剤の種類に左右される。
一般に、活性物質の濃度は1〜90%の範囲にあることが好ましい。
本発明の例示で制限されない実施例を以下に示す。
【0018】
実施例1
N-[4-メチル-2-(3-トリフルオロメチルフェニル)メトキシフェニル]シクロプロパンカルボキシアミド(C-1)の調製
N,N-ジメチルホルムアミド(DMF; 13 ml)中のN-(2-ヒドロキシ-4-メチルフェニル)シクロプロパンカルボキシアミド(1g; 5.2ミリモル)の溶液を窒素雰囲気下で維持した100 mlのフラスコで調製する。炭酸カリウムを添加し(1g; 7.2ミリモル)、その混合液を室温で撹拌しながら保ち、DMF(2ml)中の3-トリフルオロメチルベンジル(1.1g; 5.6ミリモル)の溶液を添加する。その混合液を撹拌しながら3時間60℃に加熱する。冷却後、水(150 ml)に注入し、酢酸エチル(3×50 ml)で抽出し、有機相を水(2×50 ml)で洗浄し、硫酸ナトリウムで脱水し、ろ過し、濃縮する。粗生成物(1.6g)をヘキサン/酢酸エチル8:2の混合物から結晶化し、1.3gの結晶性固形物、融点153-155℃を得る。
【0019】
実施例2
N-[4-メチル-2-(3-トリフルオロメチルフェノキシ)メチルフェニル]シクロプロパンカルボキサミド(C-2)の調製
塩化メチレン(5ml)中のシクロプロパンカルボニルクロリド(0.54g; 5.16ミリモル)の溶液を、窒素雰囲気下で維持した100 mlのフラスコ中の塩化メチレン(15 ml)中の4-メチル-2-トリフルオロメチルフェノキシメチル)アニリン(1.4g; 5ミリモル)の混合液に0℃で撹拌しながら滴下する。その混合液を撹拌しながら3時間還流温度まで加熱する。冷却後、その混合液を水(150 ml)に注入し、塩化メチレン(3×50 ml)で抽出し、有機相を水(2×50 ml)で洗浄し、硫酸ナトリウムで脱水し、ろ過し、濃縮する。1.5 gの所望の生成物を得る(1H-NMR、元素分析)。
【0020】
実施例3
上記実施例1と実施例2と同様に操作して、下記表2に示される一般式(I)を有する化合物(C)を調製した。
【0021】
【化5】
【0022】
【表3】
【0023】
【表4】
【0024】
実施例4
発芽前の除草活性と植物毒性の定量
発芽前における本発明の化合物の除草活性を次の操作手順に従って評価した。
対象(雑草又は作物)の植物種を、直径が10 cmより大きく、高さが10 cmで、砂質土壌を含むつぼに植え付けた。各々の植物種について10個のつぼを用いた。
つぼを更に2つのグループに分け、各々が各雑草又は作物について5個のつぼを有する。
植え付けの24時間後、つぼの光のシャワを止めた。湿らせた1時間後、第一グループのつぼを10容量%のアセトンと、所望の濃度の評価すべき生成物と、0.5%のトゥイーン20とを含有するヒドロアセトン分散液で処理した。
第二グループは、10容量%のアセトンと、0.5%のトゥイーン20を含有するヒドロアセトン溶液でのみ処理し、比較(ブランク)として用いた。
処理後、すべてのつぼに一様に水をかけ、次の環境状態によって条件付き環境に保持した。
- 温度: 24℃
- 相対湿度: 60%
- 光周期: 16時間
- 光の強さ: 10,000ルクス
処理の28日後、処理されない植物(ブランク)に対して処理された植物について測定した損傷%を示す、次の段階の数値に基づいて評価した。
- 0=0〜9%の損傷
- 1=10〜29%の損傷
- 2=30〜49%の損傷
- 3=50〜69%の損傷
- 4=70〜89%の損傷
- 5=90%の損傷 植物の枯死
表3は、次の植物種: アオゲイトウ(Amarantus retroflexus)(AR)、ナズナ(Capsella bursa pastoris)(CP)、アカザ(Chenopodium album)(CA)、ヤエムグラ(Galium aparine)(GA)、カミツレ(Matricaria Chamomilla)(MC)、ヒナゲシ(Papaver rhoeas)(PR)、スベリヒユ(Portulaca oleracea)(PO)、ハコベ(Stellaria media)(SM)、スズメノテッポウ(Alopecurus myosuroides)(AM)、オオクサキビ(Pnicum dicothomiflorum)(PD)、トウモロコシ(M)、コムギ(F)について500 g/haの施用量で評価した化合物C-1、C-2、C-3で得られた結果を示す表である。
【0025】
【表5】
Claims (11)
- 下記一般式(I)を有する化合物。
RaとRbは同じか又は異なる、水素原子; C1-C8アルキル基; ハロゲン原子、CN基、NO2基、C1-C4アルキル基、ハロアルキル基、アルコキシル基、ハロアルコキシル基で置換されていてもよいフェニル基又はベンジル基であり; 又はRaとRbが結合して酸素原子で中断されていてもよいC2-C8アルキレン鎖でもあり、
Rnは水素原子、又はC1-C4アルキル基又はハロアルキル基であり、
R1は水素原子、ハロゲン原子、C1-C4アルキル基又はハロアルキル基、C1-C4アルコキシル基又はハロアルコキシル基、C1-C4アルキルチオ基又はハロアルキルチオ基、シアノ基、ニトロ基であり、
R2はC1-C4アルキル基、ハロアルキル基、アルコキシル基、ハロアルコキシル基、アルキルチオ基又はハロアルキルチオ基、又はハロゲン原子であり、
XとX1は同じか又は異なる、水素原子又はハロゲン原子であり、
Aは酸素原子、-CR3R4O-基、-OCR3R4-基であり、ここで、R3とR4は同じか又は異なる、水素原子又はC1-C4アルキル基、ハロアルキル基である。) - Zがハロゲン原子であり、反応が不活性溶媒中有機塩基又は無機塩基の存在下に-20℃から反応混合物の沸点までの範囲にある温度で行われる、請求項2記載の方法。
- 除草剤としての請求項1記載の化合物の使用。
- 固体担体、液体希釈剤、界面活性剤又は他の特別な添加剤と、請求項1記載の化合物の少なくとも1種とを含む、除草剤組成物。
- 該化合物の濃度が1〜90%の範囲にある、請求項7に記載の組成物。
- 他の除草剤も含む、請求項8記載の組成物。
- 耕作面積内の雑草を防除する方法であって、請求項1記載の化合物又は請求項7記載の組成物を前記面積に施用することからなる方法。
- 活性化合物が1ヘクタール当たり1g〜1000gの範囲にある用量で施用される、請求項10記載の方法。
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EP3302053B1 (en) | 2015-06-02 | 2021-03-17 | Monsanto Technology LLC | Compositions and methods for delivery of a polynucleotide into a plant |
WO2016196782A1 (en) | 2015-06-03 | 2016-12-08 | Monsanto Technology Llc | Methods and compositions for introducing nucleic acids into plants |
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JPS49133525A (ja) * | 1973-04-27 | 1974-12-21 | ||
JPS5488231A (en) * | 1977-12-22 | 1979-07-13 | Sumitomo Chem Co Ltd | 3-phenyloxymethylaniline derivative, its preparation, and herbicides consisting of it |
JPS6072787A (ja) * | 1983-09-30 | 1985-04-24 | Hodogaya Chem Co Ltd | 感熱記録材料 |
DE19629828A1 (de) * | 1996-07-24 | 1998-01-29 | Bayer Ag | Carbanilide |
WO1999048859A1 (en) * | 1998-03-20 | 1999-09-30 | Bristol-Myers Squibb Company | Aryloxyanilides and related compounds |
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ES2305261T3 (es) | 2008-11-01 |
DE60226146D1 (de) | 2008-05-29 |
EP1414787A1 (en) | 2004-05-06 |
ITMI20011497A0 (it) | 2001-07-13 |
ATE392411T1 (de) | 2008-05-15 |
CN1527812A (zh) | 2004-09-08 |
WO2003006422A1 (en) | 2003-01-23 |
BR0211078A (pt) | 2004-06-15 |
DE60226146T2 (de) | 2009-07-02 |
JP4223947B2 (ja) | 2009-02-12 |
KR20040029364A (ko) | 2004-04-06 |
EP1414787B1 (en) | 2008-04-16 |
US20040242426A1 (en) | 2004-12-02 |
CN1252038C (zh) | 2006-04-19 |
ITMI20011497A1 (it) | 2003-01-13 |
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