KR20040029364A - 제초 작용을 갖는 치환된 아닐린 유도체 - Google Patents
제초 작용을 갖는 치환된 아닐린 유도체 Download PDFInfo
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- KR20040029364A KR20040029364A KR10-2004-7000514A KR20047000514A KR20040029364A KR 20040029364 A KR20040029364 A KR 20040029364A KR 20047000514 A KR20047000514 A KR 20047000514A KR 20040029364 A KR20040029364 A KR 20040029364A
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- South Korea
- Prior art keywords
- group
- formula
- alkyl
- halogen atom
- compound
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 13
- 150000001448 anilines Chemical class 0.000 title description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 27
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 125000003342 alkenyl 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
- 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000000203 mixture Substances 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 13
- 238000000034 method Methods 0.000 claims description 13
- 239000004009 herbicide Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 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
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 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
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- -1 phenoxy, phenoxymethyl Chemical group 0.000 description 31
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 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
- 239000002904 solvent Substances 0.000 description 7
- 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 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 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 244000234609 Portulaca oleracea Species 0.000 description 3
- 235000001855 Portulaca oleracea Nutrition 0.000 description 3
- 239000005606 Pyridate Substances 0.000 description 3
- JTZCTMAVMHRNTR-UHFFFAOYSA-N Pyridate Chemical compound CCCCCCCCSC(=O)OC1=CC(Cl)=NN=C1C1=CC=CC=C1 JTZCTMAVMHRNTR-UHFFFAOYSA-N 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- SVOAUHHKPGKPQK-UHFFFAOYSA-N 2-chloro-9-hydroxyfluorene-9-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 SVOAUHHKPGKPQK-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QGQSRQPXXMTJCM-UHFFFAOYSA-N Benfuresate Chemical compound CCS(=O)(=O)OC1=CC=C2OCC(C)(C)C2=C1 QGQSRQPXXMTJCM-UHFFFAOYSA-N 0.000 description 2
- 239000005484 Bifenox Substances 0.000 description 2
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 239000005510 Diuron Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000005572 Lenacil Substances 0.000 description 2
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 2
- LRUUNMYPIBZBQH-UHFFFAOYSA-N Methazole Chemical compound O=C1N(C)C(=O)ON1C1=CC=C(Cl)C(Cl)=C1 LRUUNMYPIBZBQH-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 241000209117 Panicum Species 0.000 description 2
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 2
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 2
- 239000005591 Pendimethalin Substances 0.000 description 2
- 239000005595 Picloram Substances 0.000 description 2
- 241000209048 Poa Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000005623 Thifensulfuron-methyl Substances 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 244000098338 Triticum aestivum Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- LUZZPGJQJKMMDM-JTQLQIEISA-N [(2s)-1-ethoxy-1-oxopropan-2-yl] 2-chloro-5-[2-chloro-4-(trifluoromethyl)phenoxy]benzoate Chemical group C1=C(Cl)C(C(=O)O[C@@H](C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 LUZZPGJQJKMMDM-JTQLQIEISA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 description 2
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- NNKKTZOEKDFTBU-YBEGLDIGSA-N cinidon ethyl Chemical group C1=C(Cl)C(/C=C(\Cl)C(=O)OCC)=CC(N2C(C3=C(CCCC3)C2=O)=O)=C1 NNKKTZOEKDFTBU-YBEGLDIGSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 2
- UOMCFEXKMQLAGJ-UHFFFAOYSA-N n-[3,4-dimethyl-2-[3-(trifluoromethyl)phenoxy]phenyl]cyclopropanecarboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1OC1=C(C)C(C)=CC=C1NC(=O)C1CC1 UOMCFEXKMQLAGJ-UHFFFAOYSA-N 0.000 description 2
- UOXONSGEGQXIAZ-UHFFFAOYSA-N n-[3-methoxy-4-methyl-2-[3-(trifluoromethyl)phenyl]phenyl]cyclopropanecarboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1C(OC)=C(C)C=CC=1NC(=O)C1CC1 UOXONSGEGQXIAZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical group 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VIXCLRUCUMWJFF-KGLIPLIRSA-N (1R,5S)-benzobicyclon Chemical compound CS(=O)(=O)c1ccc(C(=O)C2=C(Sc3ccccc3)[C@H]3CC[C@H](C3)C2=O)c(Cl)c1 VIXCLRUCUMWJFF-KGLIPLIRSA-N 0.000 description 1
- GXEKYRXVRROBEV-FBXFSONDSA-N (1r,2s,3r,4s)-7-oxabicyclo[2.2.1]heptane-2,3-dicarboxylic acid Chemical compound C1C[C@@H]2[C@@H](C(O)=O)[C@@H](C(=O)O)[C@H]1O2 GXEKYRXVRROBEV-FBXFSONDSA-N 0.000 description 1
- 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 1
- LNGRZPZKVUBWQV-UHFFFAOYSA-N (4-chloro-2-methylsulfonylphenyl)-(5-cyclopropyl-1,2-oxazol-4-yl)methanone Chemical compound CS(=O)(=O)C1=CC(Cl)=CC=C1C(=O)C1=C(C2CC2)ON=C1 LNGRZPZKVUBWQV-UHFFFAOYSA-N 0.000 description 1
- MZHCENGPTKEIGP-RXMQYKEDSA-N (R)-dichlorprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-RXMQYKEDSA-N 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-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
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-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 Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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- 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
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Abstract
R은 수소원자, C1-C8알킬 또는 할로알킬기, C2-C8알콕시알킬 또는 할로알콕시알킬기, C2-C8알케닐 또는 할로알케닐기, C2-C8알키닐 또는 할로알키닐기, 할로겐 원자 또는 C1-C4알킬 또는 할로알킬기로 치환된 C3-C8시클로알킬 또는 C4-C9시클로알킬알킬기, C1-C8알콕실 또는 할로알콕실기, NRaRb기이며; Ra및 Rb는 동일 또는 상이하고 수소원자; C1-C8알킬기; 할로겐 원자, CN기, NO2기, C1-C4알킬, 할로알킬, 알콕실, 할로알콕실기로 치환된 페닐기 또는 벤질기이거나 Ra및 Rb는 함께 산소원자가 중간에 낀 C2-C8알케닐 쇄이고; Rn은 수소원자, C1-C4알킬 또는 할로알킬기이고; R1은 수소원자, 할로겐 원자, C1-C4알킬 또는 할로알킬기, C1-C4알콕실 또는 할로알콕실, C1-C4알킬티오 또는 할로알킬티오기, 시나노기, 니트로기이고; R2는 C1-C4알킬, 할로알킬, 알콕실, 할로알콕실, 알킬티오 또는 할로알킬티오기 또는 할로겐 원자이고; X 및 X1은 동일 또는 상이하고 수소원자나 할로겐 원자이고; A는 산소 원자, -CR3R4O-기, -OCR3R4-기이고, R3및 R4는 할로겐 원자나 C1-C4알킬, 할로알킬기인 화학식1의 화합물
Description
제초 작용을 갖는 메타-치환된 아닐린 유도체가 독일 특허출원 2,855,699에 발표된다. 그러나 이 화합물은 높은 투여량을 필요로 한다는 점에서 제초제로서 만족스럽지 못하다.
다양하게 치환된 페녹시, 페녹시메틸 또는 페닐메톡시 기에 의해 아민 기에 대해 오르소 위치에서 치환된 헤테로 고리형 또는 페닐-카르복스아닐리드가 특허출원 WO98/03500에 발표된다. 위 특허출원의 생성물은 살균제 및 살충제로서 작용한다.
본 발명은 치환된 아닐린 유도체에 관계한다.
특히 본 발명은 높은 제초 작용을 갖는 오르소-치환된 아닐린 유도체, 그 제조방법 및 농작물 잡초 조절을 위한 제초제로서 용도에 관계한다.
본 출원인은 치환된 페녹시, 페녹시메틸 또는 페닐메톡시 기에 의해 아민 기에 대해 오르소 위치에서 치환된 신규 아닐린 유도체가 하나 이상의 농작물에 대해 낮은 독성과 함께 높은 제초 작용을 가짐을 발견하였다.
본 발명의 목적은 화학식1의 신규 화합물에 관계한다.
여기서 -R은 수소원자, C1-C8알킬 또는 할로알킬기, C2-C8알콕시알킬 또는 할로알콕시알킬기, C2-C8알케닐 또는 할로알케닐기, C2-C8알키닐 또는 할로알키닐기, 할로겐 원자 또는 C1-C4알킬 또는 할로알킬기로 치환된 C3-C8시클로알킬 또는 C4-C9시클로알킬알킬기, C1-C8알콕실 또는 할로알콕실기, NRaRb기이며;
-Ra및 Rb는 동일 또는 상이하고 수소원자; C1-C8알킬기; 할로겐 원자, CN기, NO2기, C1-C4알킬, 할로알킬, 알콕실, 할로알콕실기로 치환된 페닐기 또는 벤질기이거나 Ra및 Rb는 함께 산소원자가 중간에 낀 C2-C8알케닐 쇄이고;
-Rn은 수소원자, C1-C4알킬 또는 할로알킬기이고;
-R1은 수소원자, 할로겐 원자, C1-C4알킬 또는 할로알킬기, C1-C4알콕실 또는 할로알콕실, C1-C4알킬티오 또는 할로알킬티오기, 시나노기, 니트로기이고;
-R2는 C1-C4알킬, 할로알킬, 알콕실, 할로알콕실, 알킬티오 또는 할로알킬티오기 또는 할로겐 원자이고;
-X 및 X1은 동일 또는 상이하고 수소원자나 할로겐 원자이고;
-A는 산소 원자, -CR3R4O-기, -OCR3R4-기이고, R3및 R4는 할로겐 원자나 C1-C4알킬, 할로알킬기이다.
화학식1화합물의 예가 표1에 제시된다
본 발명의 또 다른 목적은 화학식1 화합물 제조방법이다.
화학식1 화합물은 화학식2의 아민 유도체를 반응식1에 따라 화학식3의 화합물과 반응시켜 제조될 수 있다.
여기서 R, Rn, R1, R2, X, X1및 A는 위와 동일한 의미를 가지며 Z는 할로겐원자, 알콕시기, 히드록시기이다.
위 공정을 수행하기위한 반응조건은 화학식3 화합물의 성질에 따라 변할 수 있다.
가령 Z가 할로겐 원자일 경우 반응은 -20℃~ 반응 혼합물의 비점의 온도에서 불활성 용매와 유기 또는 무기 염기의 존재 하에서 수행된다.
위 반응에 사용될 수 있는 용매는 물, 지방족 또는 고리 지방족 탄화수소(석유 에테르, 헥산, 시클로헥산 등), 염소 첨가된 탄화수소(염화메틸렌, 클로로포름,사염화탄소, 디클로로에탄 등), 방향족 탄화수소(벤젠, 톨루엔, 크실렌, 클로로벤젠 등), 에테르(디에틸 에테르, 디이소프로필 에테르, 디메톡시에탄, 디옥산, 테트라하이드로퓨란 등), 에스테르(에틸 아세테에트 등), 케톤(아세톤, 메틸에틸케톤, 메틸프로필케톤, 메틸이소부틸케톤 등), 니트릴(아세토니트릴, 벤조니트릴 등), 비-양성자 2극성 용매(디메틸포름아미드, 디메틸아세트아미드, 헥사메틸포스포로트리아미드, 디메틸술폭사이드, 술포란, N-메틸피롤리돈 등)이다.
사용될 수 있는 무기 염기는 수산화물, 탄산 및 중탄산 나트륨 및 칼륨이다.
사용 가능한 유기 염기는 트리에틸아민, 피리딘, 4-N,N-디메틸아미노피리딘, 디아자비시클로옥탄(DABCO), 디아자비시클로노넨(DBN), 디아자비시클로운데센(DBU)이다.
혹은 화학식1 화합물(A가 -CR3R4O-기인)은 화학식4의 유도체를 화학식5의 페놀과 축합시켜 제조될 수 있는데 반응식2에 따라 화학식1a의 에테르가 생성된다.
여기서 R, Rn, R1, R2, R3, R4,X, X1및 A는 위와 동일한 의미를 가지며 Z1은 할로겐원자, 특히 염소나 브롬 또는 RZSO3기이고 RZ는 C1-C4알킬기 또는 C1-C4알킬기로 치환된 페닐기이다.
에테르화 반응은 -10℃~ 반응 혼합물의 비점의 온도에서 하나 이상의 불활성 유기용매와 염기, 특히 무기염기의 존재 하에서 수행된다.
위 반응에 사용될 수 있는 용매는 방향족 탄화수소(벤젠, 톨루엔, 크실렌, 클로로벤젠 등), 에테르(디에틸 에테르, 디이소프로필 에테르, 디메톡시에탄, 디옥산, 테트라하이드로퓨란 등), 알코올 및 글리콜(메탄올, 에탄올, 메틸셀로솔브, 에틸렌 글리콜 등), 케톤(아세톤, 메틸에틸케톤, 메틸프로필케톤, 메틸이소부틸케톤 등), 니트릴(아세토니트릴, 벤조니트릴 등), 비-양성자 2극성 용매(디메틸포름아미드, 디메틸아세트아미드, 헥사메틸포스포로트리아미드, 디메틸술폭사이드, 술포란, N-메틸피롤리돈 등)이다.
사용될 수 있는 무기 염기는 수소화나트륨 또는 칼륨, 수산화물, 탄산염이다.
반응은 용매로서 물과 비-혼화성 유기용매를 사용한 2상 시스템에서 상 전이 촉매의 존재 하에서 Dehmlow & Dehmlow(상 전이 촉매반응(1983), Verlag Chemie)에 따라 수행될 수 있다.
유사하게 화학식1 화합물(A가 -CR3R4O-기인)은 화학식6의 페놀을 화학식7의 유도체와 반응시켜 제조될 수 있는데 반응식3에 따라 화학식1b의 에테르가 생성된다.
여기서 R, Rn, R1, R2, R3, R4,X, X1및 A는 위와 동일한 의미를 가지며 Z1은 할로겐원자, 특히 염소나 브롬 또는 RZSO3기이고 RZ는 C1-C4알킬기 또는 C1-C4알킬기로 치환된 페닐기이다.
반응식3의 에테르화 반응에서 사용될 수 있는 공정절차, 용매 및 염기의 종류는 반응식2에서 지정된 것과 동일하다.
화학식2,3,4,5,6,7의 중간물질은 유기화학의 공지 방법에 따라 용이하게 제조될 수 있다.
화학식1의 화합물은 농장에서 사용하기에 적합하여 유용한 작물을 잡초로부터 보호하는 높은 제초력을 갖는다.
본 발명의 화합물은 외떡잎 및 쌍떡잎 잡초의 발생 전후 조절에 효과적이다.동시에 이들 화합물은 발생 전후 처리에서 유용한 작물에 대한 독성 효과를 보이지 않는다.
화학식1의 화합물을 사용하여 효과적으로 조절될 수 있는 작물은 아부틸론 테오프라스티(Abutilon theofrasti), 알리스마 플란타고(Alisma plantago), 아마란투스 에스피피.(Amaranthus spp.), 암니 마이우스(Amni maius), 캡셀라 버사 파스토리스(Capsella bursa pastoris), 케노포듐 알범(Chenopodium album), 콘볼벌러스 세퓸(Convolvulus sepium), 갈륨 아파린(Galium aparine), 제라늄 디섹텀(Geranium dissectum), 이포미아 에스피피.(Ipomea spp.), 파파베르 로이아스(Papaver rhoeas), 파세오루스 아우레우스(Phaseolus aureus), 폴리고넘 페리시카리아(Polygonum persicaria), 포르툴아카 올레라시아(Portulaca oleracea), 시다 스피노사(Sida spinosa), 시나피스 아르벤시스(Sinapis arvensis), 솔라넘 니그럼(Solanum nigrum), 스텔라리아 메디아(Stellaria media), 베로니카 에스피피.(Veronica spp.), 비올라 에스피피.(Viola spp.), 크산튬 에스피피.(Xanthium spp.), 알로페쿠루스 미오수로이데스(Alopecurus myosuroides), 아베나 파투아(Avena fatua), 시페루스 에스피피.(Cyperus spp.), 디지타리아 산구이날리스(Digitaria sanguinalis), 에키노클로아 에스피피.(Echinocloa spp.), 헬레오카리스 아비큘라리스(Heleocaris avicularis), 헤테란테라 에스피피.(Heteranthera spp.), 파니큠 에스피피.(Panicum spp.), 포아 에스피피.(Poa spp.), 스시르푸스 에스피피.(Scirpus spp.), 소검 에스피피.(Sorghum spp.)이다.
농업에 적용되는 투여량을 사용하면 위 화합물은 쌀(오리자 사티바), 밀(트리티컴 에스피.), 보리(호데움 벌가레), 옥수수(지아 메이스), 콩(글리신 맥스)과 같은 중요한 작물에 독성을 보이지 않는다.
본 발명의 또 다른 목적은 화학식1의 화합물을 적용하여 경작지에서 잡초를 조절하는 방법에 관계한다.
필요한 효과를 얻기 위해 적용될 화합물의 양은 사용된 화합물, 보호될 작물, 파괴될 잡초, 횡행 정도, 기후 조건, 지면의 특성, 적용방법과 같은 다양한 인자에 따라 가변적이다.
1헥타아르당 1-1000g의 화합물 투여로 충분한 조절이 가능하다.
농업에 사용하기 위해 활성 물질로서 하나 이상의 화학식1 화합물을 함유한 제초 작용이 있는 조성물을 사용하는 것이 종종 유리하다.
조성물은 건조 분말, 습윤 가능한 분말, 유화 가능한 농축물, 마이크로 에멀젼, 페이스트, 과립, 용액, 현탁액 형태로 사용될 수 있으며 조성물 타입의 선택은 용도에 달려있다.
조성물은 가령 계면활성제의 존재 하에서 활성 물질을 용매나 고체 희석 매체로 희석 또는 용해시켜 제조된다.
카올린, 알루미나, 실리카, 탈크, 벤토나이트, 초크, 석영, 돌로마이트, 애터펄자이트, 몬트모릴로나이트, 규조토, 셀룰로오스, 전분 등이 고체 불활성 희석제 또는 담체로 사용될 수 있다.
물이나 방향족 탄화수소(크실올, 알킬벤졸 혼합물 등), 지방족 탄화수소(헥산, 시클로헥산 등), 할로겐화 방향족 탄화수소(클로로벤졸 등), 알코올(메탄올, 프로판올, 부탄올, 옥탄올 등), 에스테르(이소부틸 아세테이트 등), 케톤(아세톤, 시클로헥산온, 아세토페논, 이소포론, 에틸아밀케톤 등), 식물성 오일 또는 광유나 이의 혼합물과 같은 유기 용매가 액체 불활성 희석제로 사용될 수 있다.
비-이온성(폴리에톡시화 알킬페놀, 폴리에톡시화 지방산 알코올 등), 음이온성(알킬벤젠술포네이트, 알킬술포네이트 등), 양이온성(알킬암모늄의 4차 염 등) 습윤제 및 유화제가 계면활성제로 사용될 수 있다.
분산제(예, 리그닌과 이의 염, 셀룰로오스 유도체, 알기네이트 등), 안정화제(예, 항산화제, 자외선 흡수제 등)이 첨가될 수도 있다.
위 조성물의 작용범위를 확장시키기 위해서 다른 제초제, 살균제, 살충제, 진드기 제거제, 비료와 같은 다른 활성 성분을 첨가할 수도 있다.
화학식1의 화합물을 하나 이상 함유한 조성물에 첨가될 수 있는 다른 제초제의 예는 아세토클로르(acetochlor), 아시플루오르펜(acifluorfen), AKH-7088, 알라클로르(alachlor), 알록시딤(alloxydim), 아메트린(ametryn), 아미카바존(amicarbazone), 아미도술퓨란(amidosulfuron), 아미트롤(amitrole), 아닐로포스(anilofos), 아수람(asulam), 아트라진(atrazine), 아자페니딘(azafenidin), 아짐술퓨론(azimsulfuron), 아지프로트리네(aziprotryne), BAY MKH 6561, 베플루부타미드(beflubutamid), 벤아졸린(benazolin), 벤플루랄린(benfluralin), 벤퓨레세이트(benfuresate), 벤술퓨론(bensulfuron), 벤술라이드(bensulide), 벤타존(bentazone),벤즈펜디존(benzfendizone), 벤조비시클론(benzobicyclon), 벤조페납(benzofenap), 벤즈티아주론(benzthiazuron), 비페녹스(bifenox), 빌라나포스(bilanafos), 비스피리박-소듐(bispyribac-sodium), 브로마실bromacil), 브로모부타이드(bromobutide), 브로모펜옥심(bromofenoxim), 브로모옥시닐(bromoxynil), 부타클로르(butachlor), 부타펜아실(butafenzcil), 부타미포스(butamifos), 부텐아클로르(butenachlor), 부트랄린(butralin), 부트록시딤(butroxydim), 부틸레이트(butylate), 카펜스트롤(cafenstrole), 카베타미드(carbetamide), 카펜트라존-에틸(carfentrazone-ethyl), 클로메톡시펜(chlomethoxyfen), 클로르암벤(chloramben), 클로르브로뮤론(chlorbromuron), 클로르뷰팜(chlorbufam), 클로르플루레놀(chlorflurenol), 클로르이다존(chloridazon), 클로르이뮤론(chlorimuron), 클로르니트로펜(chlornitrofen), 클로르오톨유론(chlorotoluron), 클로록스유론(chloroxuron), 클로르프로팜(chlorpropham), 클로르술퓨론(chlorsulfuron), 클로르탈(chlorthal), 클로르티아미드(chlorthiamid), 시니돈 에틸(cinidon ethyl), 신메틸린(cinmethylin), 시노술퓨론(cinosulfuron), 클레토딤(clethodim), 클로디나폽(clodinafop), 클로마존(clomazone), 클로메프롭(clomeprop), 클로피랄리드(clopyralid), 클로란술람-메틸(cloransulam-methyl), 큐밀유론(JC-940)(cumyluron JC-940)), 시아나진(cyanazine), 시클로에이트(cycloate), 시클로술팜유론(cyclosulfamuron), 시클로옥시딤(cycloxydim), 시할로폽-부틸(cyhalofop-butyl), 2,4-D,2,4-DB, 다이뮤론(daimuron), 달라폰(dalapon),데스메디팜(desmedipham), 데스메트린(desmetryn), 디캄바(dicamba), 디클로로벤일(dichlobenil), 디클로르프롭(dichlorprop), 디클로르프롭-P(dichlorprop-P), 디클로폽(diclofop), 디클로술람(diclosulam), 디에타틸(dithatyl), 디페녹스유론(difenoxuron), 디펜조쿠아트(difenzoquat), 디플루페니칸(diflufenican), 디플루펜조피르(diflufenzopyr), 디메퓨론(dimefuron), 디메피페레이트(dimepiperate), 디메타클로르(dimethachlor), 디메타메트린(dimethametryn), 디메텐아미드(dimethenamid), 디니트라민(dinitramine), 디노세브(dinoseb), 디노세브 아세테이트(dinoseb acetate), 디노터브(dinoterb), 디펜아미드(diphenamid), 디프로페트린(dipropetryn), 디큐아트(diquat), 디티오피르(dithiopyr), 1-디유론(1-diuron), 에글린아진(eglinazine), 엔도탈(endothal), EPTC, 에스프로카브(esprocarb), 에탈플루랄린(ethalfluralin), 에타메트술퓨론-메틸(ethametsulfuron-methyl), 에티딤유론(ethidimuron), 에티오진(SMY 1500)(ethiozin (SMY-1500)), 에토퓸에세이트(ethofumesate), 에톡시펜-에틸(HC-252)(ethoxyfen-ethyl(HC-252)), 에톡시술퓨론(ethoxysulfuron), 에토벤자니드(HW52)(etobenzanid (HW 52)), 펜옥사프롭(fenoxaprop), 펜옥사프롭-P(fenoxaprop-P), 펜트라자미드(fentrazamide), 펜유론(fenuron), 플람프롭(flamprop), 플람프롭-M(flamprop-M), 플라자술퓨론(flazasulfuron), 플로라술람(florasulam), 플루아지폽(fluazifop), 플루아지폽-P(fluazifop-P), 플루아졸레이트(JV 485)(fluazolate(JV 485), 플루카바존-소듐(flucarbazone-sodium), 플루클로랄린(fluchloralin), 플루펜아세트(flufenacet), 플루메트술람(flumetsulam), 플루이클로락-펜틸(flumiclorac-pentyl), 플루미옥사진(flumioxazin), 플루미프로핀(flumipropin), 플루메트유론(fluometuron), 플루오로글리코펜(fluoroglycofen), 플루오로니트로펜)(fluoronitrofen), 플루폭삼(flupoxam), 플루프로파네이트(flupropanate), 플루피르술퓨론(flupyrsulfuron), 플루레놀(flurenol), 플루리돈(fluridone), 플루오로클로리돈(flurochloridone), 플루록시피르(fluroxypyr), 플루르트아몬(flurtamone), 플루티아세트-메틸(fluthiacet-methyl), 포메사펜(fomesafen), 포람술퓨론(foramsulfuron), 포사민(fosamine), 퓨릴옥시펜(furyloxyfen), 글루포시네이트(glufosinate), 글리포세이트(glyphosate), 할로술퓨론-메틸(halosulfuron-methyl), 할옥시폽(haloxyfop), 할옥시폽-P-메틸(haloxyfop-P-methyl), 헥사진온(hexazinone), 아마자큐인(imazamethabenz), 이마제타피르(imazamox), 아마조술퓨론(imazosulfuron), 인다노판(indanofan), 아이오도술퓨론(iodosulfuron), 아이옥시닐(ioxynil), 이소프로팔린(isopropalin), 이소프로튜론(isoproturon), 이소유론(isouron), 이속사벤(isoxaben), 이속사클로르톨레(isoxachlortole), 이속사플루톨(isoxaflutole), 이속사피리폽(isoxapyrifop), KPP-421, 락토펜(lactofen), 레나실(lenacil), 린유론(linuron), LS830556, MCPA, MCPA-티오에틸(thioethyl), MCPB, 메코프롭(mecoprop), 메코프롭-P(mecoprop-P), 메펜아세트(mefenacet), 메소트리온(mesotrione), 메타미트론(metamitron), 메타자클로르(metazachlor), 메타벤즈티아주론(methabenzthiazuron), 메타졸(methazole), 메토프로트리네(methoprotryne), 메틸딤론(methyldymron), 메토벤즈유론(metobenzuron), 메토브로뮤론(metobromuron), 메토라클로르(methlachlor), S-메토라클로르(S-metolachlor), 메토술람(metosulam), 메톡스유론(metoxuron), 메트리뷰진(metribuzin), 메트술퓨론(metsulfuron), 몰리네이트(molinate), 모날리드(monalide), 모노린유론(monolinuron), 나프로아닐리드(naproanilide), 나프롭아미드(napropamide), 나프탈람(naptalam), NC-330, 네뷰론(neburon), 니코술퓨론(nicosulfuron), 니피라클로펜(nipyraclofen), 노르플루라존(norflurazon), 오르벤카브(orbencarb), 오리잘린(oryzalin), 옥사디아르질(oxadiargyl), 옥사디아존(oxadiazon), 옥사술퓨론(oxasulfuron), 옥사지클로메폰(oxaziclomefone), 옥시플루오르펜(oxyflurofen), 파라큐아트(paraquat), 페뷸레이트(pebulate), 펜디메타린(pendimethalin), 펜타노클로르(pentanochlor), 펜톡사존(pentoxazone), 펜톡사미드(penthoxamid), 펜메디팜(phenmedipham), 피클로람(picloram), 피콜리나펜(picolinafen), 피페로포스(piperophos), 프레틸라클로르(pretilachlor), 프리미술퓨론(primisulfuron), 프로디아민(prodimine), 프로플루아졸(profluazol), 프로글리나진(proglinazine), 프로메톤(prometon), 프로메트리네(prometryne), 프로파클로르(propachlor), 프로파닐(propanil), 프로파큐니자폽(propaquizafop), 프로파진(propazine), 프로팜(propham), 프로피소클로르(propisochlor), 프로피자미드(propyzamide), 프로술포카브(prosulfocarb), 프로술퓨론(prosulfuron), 피라클로닐(pyraclonil), 피라플루펜에틸(pyraflufenethyl), 피라졸리네이트(pyrazolynate), 피라조술퓨론(pyrazosulfuron), 피라족시펜(pyrazoxyfen), 피리벤족심(pyribenzoxim), 피리부티카브(pyributicarb), 피리다폴(pyridafol), 피리데이트(pyridate), 피리프탈리드(pyriftalid), 피리미노박-메틸(pyriminobac-methyl), 피리티오박-소듐(pyrithiobac-sodium), 큐인클로락(quinclorac), 큐인메락(quinmerac), 큐이잘로폽(quizalofop), 큐이잘로폽-P(quizalofop-P), 림술퓨론(rimsulfuron), 세톡시딤(sethoxydim), 시듀론(siduron), 시마진(simazine), 시메트린(simetryn), 술코트리온(sulcotrione), 술펜트라존(sulfentrazone), 술포메튜론-메틸(sulfometuron-methyl), 술포술퓨론(sulfosulfuron), 2,3,6-TBA, TCA-소듐(sodium), 테뷰탐(tebutam), 테뷰티유론(tebuthiuron), 테프랄옥시딤(tepraloxydim), 테바실(terbacil), 테뷰메톤(terbumeton), t-부틸-아진(terbuthyl-azine), 테뷰티린(terbutryn), 테닐클로르(thenylchlor), 티아자플루론(thiazafluron), 티아조피르(tiazopyr), 티디아지민(thidiazimin), 티펜술퓨론-메틸(thifensulfuron-methyl), 티오벤카브(thiobencarb), 티오카바질(tiocarbazil), 티오클로림(tioclorim), 트랄콕시딤(tralkoxydim), 트리-알레이트(tri-allate), 트리아술퓨론(triasulfuron), 트리아지플람(triaziflam), 트리벤유론(tribenuron), 트리클로피르(triclopyr), 트리에타진(trietazine), 트리플록시술퓨론(trifloxysulfuron), 트리플루랄린(trifluralin), 트리플루술퓨론-메틸(triflusulfuron-methyl), 트리토술퓨론(tritosulfuron), UBI-C4874, 베르놀레이트(vernolat)이다.
위 조성물에서 활성물질의 농도는 활성 화합물, 적용분야, 환경 조건 및 사용된 배합물의 형태에 따라 가변적이다.
일반적으로 활성물질의 농도는 1-90%이다.
실시예1:N-[4-메틸-2-(3-트리플루오로메틸페닐)-메톡시페닐]시클로프로판카르복스아미드(C-1)제조
N,N-디메틸포름아미드(DMF 13ml)에 용해된 N-(2-히드록시-4-메틸페닐)시클로프로판카르복스아미드(1g;5.2밀리몰) 용액이 질소 대기 하에서 유지된 100ml 플라스크에서 제조된다. 탄산칼륨(1g;7.2밀리몰)이 첨가되고 혼합물을 실온에서 교반 하에 유지하고 DMF(2ml)에 용해된 3-트리플루오로메틸벤질 클로라이드(1.1g;5.6밀리몰) 용액이 첨가된다. 혼합물을 3시간 동안 교반 하에서 60℃로 가열한다. 냉각시킨 후에 150ml의 물에 붓고 에틸아세테이트(3×50ml)로 추출하고 유기상을 물(2×50ml)로 세척하고 황산나트륨으로 무수화 하고 여과 및 농축한다. 8:2의 헥산/에틸아세테이트 혼합물에서 생성물(1.6G)이 결정화 된다. 153-155℃의 융점을 갖는 결정성 고체 1.3G이 수득된다.
실시예2:N-[4-메틸-2-(3-트리플루오로메틸페녹시)-메틸페닐]시클로프로판카르복스아미드(C-2)제조
염화메틸렌(5ml)에 용해된 시클로프로판카르보닐 클로라이드(0.54G;5.16밀리몰) 용액이 0℃에서 교반 하에서 질소 대기 하에서 유지된 100ml 플라스크에서 염화메틸렌 15ml에 용해된 4-메틸-2-트리플루오로메틸-페녹시메틸)아닐린(1.4g;5밀리몰) 및 트리에틸아민(0.55g;5.44밀리몰)의 혼합물에 적가된다. 혼합물을 3시간 동안 교반 하에서 환류온도로 가열한다. 냉각시킨 후에 150ml의 물에 붓고 염화메틸렌(3×50ml)으로 추출하고 유기상을 물(2×50ml)로 세척하고 황산나트륨으로 무수화 하고 여과 및 농축한다. 1.5g의 생성물이 수득된다(1H-NMR, 원소분석).
실시예3
실시예1 및 2와 유사하게 공정을 수행하여 표2에 표시된 화학식1의 화합물(C)이 제조된다.
(화학식1)
실시예4
잡초 발생 전 제초 작용 및 식물 독성의 측정
다음 절차에 따라 발생 전 본 발명 화합물의 제초 작용이 평가된다.
10cm 직경과 10cm 높이를 가지며 사질 토양을 함유한 병에 식물종(잡초나 작물)을 심는다. 각 식물종에 대해 배개의 병이 사용된다.
병을 두 그룹으로 나누고 각 잡초나 작물에 대해 5개의 병을 포함한다.
24시간 후에 병을 약간 축축하게 한다. 습윤 1시간 후에 제1그룹의 병을 10부피% 아세톤, 필요한 농도의 평가될 제품 및 0.5% Tween20을 함유한 하이드로-아세톤 분산물로 처리한다.
제2그룹은 10부피% 아세톤과 0.5% Tween20을 함유한 하이드로-아세톤 용액으로 처리하고 비교기준(블랭크)으로 사용한다.
처리 후에 모든 병을 균일하게 물을 주고 다음 조건 하에서 조절된 환경에 유지한다.
-온도:24℃
-상대습도:60%
-광 조사 기간:16시간
-빛의 세기:10,000룩스
처리 28일 후에 처리안된 것(블랭크)에 대해 처리된 식물에서 측정되는 피해 비율로 제초 작용이 평가된다:
-0=0-9% 피해
-1=10-29% 피해
-2=30-49% 피해
-3=50-69% 피해
-4=70-89% 피해
-5=90% 피해~ 식물의 죽음
표3은 다음 식물종에 대해 500g/ha의 투여량에서 평가된 화합물C-1, C-2 및 C-3로 수득되는 결과를 보여준다.
아마란투스 리트로플렉서스(AR), 캡셀라 버사 파스토리스(CP), 케노포듐 알범(CA), 갈륨 아파린(GA), 매트리카리아 카모밀라(MC), 파파버 로이아스(PR), 포르툴라카 올레라시아(PO), 스텔라리아 메디아(SM), 알로페쿠루스 미오수로이데스(AM), 파니쿰 디코토미플로룸(PD), 마이즈(M), 밀(F).
Claims (11)
- 화학식1의 화합물(화학식1)여기서 -R은 수소원자, C1-C8알킬 또는 할로알킬기, C2-C8알콕시알킬 또는 할로알콕시알킬기, C2-C8알케닐 또는 할로알케닐기, C2-C8알키닐 또는 할로알키닐기, 할로겐 원자 또는 C1-C4알킬 또는 할로알킬기로 치환된 C3-C8시클로알킬 또는 C4-C9시클로알킬알킬기, C1-C8알콕실 또는 할로알콕실기, NRaRb기이며;-Ra및 Rb는 동일 또는 상이하고 수소원자; C1-C8알킬기; 할로겐 원자, CN기, NO2기, C1-C4알킬, 할로알킬, 알콕실, 할로알콕실기로 치환된 페닐기 또는 벤질기이거나 Ra및 Rb는 함께 산소원자가 중간에 낀 C2-C8알케닐 쇄이고;-Rn은 수소원자, C1-C4알킬 또는 할로알킬기이고;-R1은 수소원자, 할로겐 원자, C1-C4알킬 또는 할로알킬기, C1-C4알콕실 또는 할로알콕실, C1-C4알킬티오 또는 할로알킬티오기, 시나노기, 니트로기이고;-R2는 C1-C4알킬, 할로알킬, 알콕실, 할로알콕실, 알킬티오 또는 할로알킬티오기 또는 할로겐 원자이고;-X 및 X1은 동일 또는 상이하고 수소원자나 할로겐 원자이고;-A는 산소 원자, -CR3R4O-기, -OCR3R4-기이고, R3및 R4는 할로겐 원자나 C1-C4알킬, 할로알킬기이다.
- 화학식2의 아민 유도체가 반응식1에 따라 화학식3의 화합물과 반응됨을 특징으로 하는 화학식1 화합물 제조방법(반응식1)여기서 R, Rn, R1, R2, X, X1및 A는 위와 동일한 의미를 가지며 Z는 할로겐원자, 알콕시기, 히드록시기이다.
- 제2항에 있어서, Z가 할로겐 원자이고 -20℃~ 반응 혼합물의 비점의 온도에서 불활성 용매와 유기 또는 무기 염기의 존재 하에서 반응이 수행됨을 특징으로하는 방법
- 화학식4의 유도체를 화학식5의 페놀과 축합시켜 반응식2에 따라 화학식1a의 에테르를 생성하는 단계를 포함하며 반응은 -10℃~반응 혼합물의 비점에 해당하는 온도에서 하나 이상의 불활성 유기용매와 염기의 존재 하에서 수행되는 A가 -CR3R4O-기인 화학식1 화합물 제조방법(반응식 2)여기서 R, Rn, R1, R2, R3, R4,X, X1및 A는 위와 동일한 의미를 가지며 Z1은 할로겐원자 또는 RZSO3기이고 RZ는 C1-C4알킬기 또는 C1-C4알킬기로 치환된 페닐기이다.
- 화학식6의 페놀을 화학식7의 유도체와 반응시켜 반응식3에 따라 화학식1b의 에테르를 생성하는 단계를 포함하며 반응은 -10℃~반응 혼합물의 비점에 해당하는 온도에서 하나 이상의 불활성 유기용매와 염기의 존재 하에서 수행되는 A가 -CR3R4O-기인 화학식1 화합물 제조방법(반응식 3)여기서 R, Rn, R1, R2, R3, R4,X, X1및 A는 위와 동일한 의미를 가지며 Z2는 할로겐원자, 특히 염소나 브롬 또는 RZSO3기이고 RZ는 C1-C4알킬기 또는 C1-C4알킬기로 치환된 페닐기이다.
- 제초제로서 제1항의 화합물
- 고체 담체, 액체 희석제, 계면활성제 또는 다른 첨가제와 화학식1의 화합물을 포함한 제초제 조성물
- 제7항에 있어서, 화합물의 농도가 1-90%임을 특징으로 하는 조성물
- 제8항에 있어서, 다른 제초제를 포함하는 조성물
- 제1항의 화합물이나 제7항의 조성물을 경작지에 적용하는 단계를 포함하는 잡초 조절방법
- 제10항에 있어서, 활성 화합물이 1-1000g/ha의 투여량으로 적용됨을 특징으로 하는 방법
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ITMI01A001497 | 2001-07-13 | ||
IT2001MI001497A ITMI20011497A1 (it) | 2001-07-13 | 2001-07-13 | Nuovi derivati di aniline sostituite ad attivita' erbicida |
PCT/IB2002/002790 WO2003006422A1 (en) | 2001-07-13 | 2002-07-12 | New derivatives of substituted anilines with herbicidal activity |
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CN (1) | CN1252038C (ko) |
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US8097712B2 (en) | 2007-11-07 | 2012-01-17 | Beelogics Inc. | Compositions for conferring tolerance to viral disease in social insects, and the use thereof |
US8962584B2 (en) | 2009-10-14 | 2015-02-24 | Yissum Research Development Company Of The Hebrew University Of Jerusalem, Ltd. | Compositions for controlling Varroa mites in bees |
US20130047297A1 (en) | 2010-03-08 | 2013-02-21 | Robert D. Sammons | Polynucleotide molecules for gene regulation in plants |
US10760086B2 (en) | 2011-09-13 | 2020-09-01 | Monsanto Technology Llc | Methods and compositions for weed control |
CN103930549B (zh) | 2011-09-13 | 2020-09-18 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
EP3382027A3 (en) | 2011-09-13 | 2018-10-31 | Monsanto Technology LLC | Methods and compositions for weed control |
CA2848695A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and composition for weed control comprising inhibiting ppg oxidase |
US10806146B2 (en) | 2011-09-13 | 2020-10-20 | Monsanto Technology Llc | Methods and compositions for weed control |
WO2013040117A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control |
CN107739737A (zh) | 2011-09-13 | 2018-02-27 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
AU2012308694B2 (en) | 2011-09-13 | 2018-06-14 | Monsanto Technology Llc | Methods and compositions for weed control |
US10829828B2 (en) | 2011-09-13 | 2020-11-10 | Monsanto Technology Llc | Methods and compositions for weed control |
AR091143A1 (es) | 2012-05-24 | 2015-01-14 | Seeds Ltd Ab | Composiciones y metodos para silenciar la expresion genetica |
US10683505B2 (en) | 2013-01-01 | 2020-06-16 | Monsanto Technology Llc | Methods of introducing dsRNA to plant seeds for modulating gene expression |
BR112015015976A2 (pt) | 2013-01-01 | 2018-04-10 | A. B. Seeds Ltd. | método para introduzir dsrna em sementes para modular a expressão genética |
AU2014248958A1 (en) | 2013-03-13 | 2015-10-01 | Monsanto Technology Llc | Methods and compositions for weed control |
EP3604535A3 (en) | 2013-03-13 | 2020-04-22 | Monsanto Technology LLC | Methods and compositions for weed control |
US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
EP3608412A3 (en) | 2013-07-19 | 2020-04-08 | Monsanto Technology LLC | Compositions and methods for controlling leptinotarsa |
US9850496B2 (en) | 2013-07-19 | 2017-12-26 | Monsanto Technology Llc | Compositions and methods for controlling Leptinotarsa |
US9540642B2 (en) | 2013-11-04 | 2017-01-10 | The United States Of America, As Represented By The Secretary Of Agriculture | Compositions and methods for controlling arthropod parasite and pest infestations |
UA119253C2 (uk) | 2013-12-10 | 2019-05-27 | Біолоджикс, Інк. | Спосіб боротьби із вірусом у кліща varroa та у бджіл |
WO2015108982A2 (en) | 2014-01-15 | 2015-07-23 | Monsanto Technology Llc | Methods and compositions for weed control using epsps polynucleotides |
WO2015153339A2 (en) | 2014-04-01 | 2015-10-08 | Monsanto Technology Llc | Compositions and methods for controlling insect pests |
CN106795515B (zh) | 2014-06-23 | 2021-06-08 | 孟山都技术公司 | 用于经由rna干扰调控基因表达的组合物和方法 |
EP3161138A4 (en) | 2014-06-25 | 2017-12-06 | Monsanto Technology LLC | Methods and compositions for delivering nucleic acids to plant cells and regulating gene expression |
UA125244C2 (uk) | 2014-07-29 | 2022-02-09 | Монсанто Текнолоджі Елелсі | Спосіб умертвіння або припинення росту комахи |
PL3256589T3 (pl) | 2015-01-22 | 2022-02-21 | Monsanto Technology Llc | Kompozycje i sposoby kontrolowania leptinotarsa |
EP3302053B1 (en) | 2015-06-02 | 2021-03-17 | Monsanto Technology LLC | Compositions and methods for delivery of a polynucleotide into a plant |
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WO2003006422A1 (en) | 2003-01-23 |
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JP4223947B2 (ja) | 2009-02-12 |
US20040242426A1 (en) | 2004-12-02 |
ES2305261T3 (es) | 2008-11-01 |
ITMI20011497A0 (it) | 2001-07-13 |
JP2004534096A (ja) | 2004-11-11 |
EP1414787A1 (en) | 2004-05-06 |
BR0211078A (pt) | 2004-06-15 |
DE60226146D1 (de) | 2008-05-29 |
ITMI20011497A1 (it) | 2003-01-13 |
CN1252038C (zh) | 2006-04-19 |
EP1414787B1 (en) | 2008-04-16 |
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