WO2010038953A2 - 우라실계 화합물 및 이를 포함하는 제초제 - Google Patents
우라실계 화합물 및 이를 포함하는 제초제 Download PDFInfo
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- WO2010038953A2 WO2010038953A2 PCT/KR2009/005471 KR2009005471W WO2010038953A2 WO 2010038953 A2 WO2010038953 A2 WO 2010038953A2 KR 2009005471 W KR2009005471 W KR 2009005471W WO 2010038953 A2 WO2010038953 A2 WO 2010038953A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- methyl
- compound
- trifluoromethyl
- formula
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 128
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title claims abstract description 56
- 239000004009 herbicide Substances 0.000 title claims abstract description 42
- 229940035893 uracil Drugs 0.000 title claims abstract description 40
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- -1 uracil compound Chemical class 0.000 claims description 128
- 241000196324 Embryophyta Species 0.000 claims description 61
- 239000000126 substance Substances 0.000 claims description 40
- 230000002363 herbicidal effect Effects 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 239000003112 inhibitor Substances 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 238000005660 chlorination reaction Methods 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000002689 soil Substances 0.000 claims description 9
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 8
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 229930192334 Auxin Natural products 0.000 claims description 6
- 229910005965 SO 2 Inorganic materials 0.000 claims description 6
- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 239000002363 auxin Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- NBFQYHKHPBMJJV-UHFFFAOYSA-N risocaine Chemical group CCCOC(=O)C1=CC=C(N)C=C1 NBFQYHKHPBMJJV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000000887 hydrating effect Effects 0.000 claims description 4
- 125000006606 n-butoxy group Chemical group 0.000 claims description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 4
- 239000000375 suspending agent Substances 0.000 claims description 4
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 3
- 102000004316 Oxidoreductases Human genes 0.000 claims description 3
- 108090000854 Oxidoreductases Proteins 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 235000021466 carotenoid Nutrition 0.000 claims description 3
- 150000001747 carotenoids Chemical class 0.000 claims description 3
- 102000005396 glutamine synthetase Human genes 0.000 claims description 3
- 108020002326 glutamine synthetase Proteins 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 230000011278 mitosis Effects 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- CQJZYCPPVCVUPD-UHFFFAOYSA-N (2-methoxy-2-oxoethyl) 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCC(=O)OCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F CQJZYCPPVCVUPD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- PLWGHANIYYVMTJ-UHFFFAOYSA-N C1=C(Cl)C(OC(C)C(=O)NCCC(O)=O)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCC(O)=O)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F PLWGHANIYYVMTJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- ABOUNYBYEZXVMO-UHFFFAOYSA-N benzyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C=1C=CC=CC=1COC(=O)CCNC(=O)C(C)OC(C(=CC=1F)Cl)=CC=1N1C(=O)C=C(C(F)(F)F)N(C)C1=O ABOUNYBYEZXVMO-UHFFFAOYSA-N 0.000 claims description 2
- ABVIBIBUSITOQE-UHFFFAOYSA-N butyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCC(=O)OCCCC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F ABVIBIBUSITOQE-UHFFFAOYSA-N 0.000 claims description 2
- 210000002421 cell wall Anatomy 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- SSYITWKQTGXRQL-UHFFFAOYSA-N ethyl 4-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]butanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCCC(=O)OCC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F SSYITWKQTGXRQL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 2
- 125000005155 haloalkylene group Chemical group 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- OJALDKSHYRDKJX-UHFFFAOYSA-N methyl 3-[2-[2-carbamothioyl-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(C(N)=S)C(OC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F OJALDKSHYRDKJX-UHFFFAOYSA-N 0.000 claims description 2
- ARICQDAPAZQPCI-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]anilino]propanoylamino]propanoate Chemical compound C1=C(Cl)C(NC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F ARICQDAPAZQPCI-UHFFFAOYSA-N 0.000 claims description 2
- GRFKZCSPZSAKKI-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoyl-hydroxyamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)N(O)CCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GRFKZCSPZSAKKI-UHFFFAOYSA-N 0.000 claims description 2
- NYFXXJUWJMOHNJ-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoyl-methoxyamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)N(CCC(=O)OC)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F NYFXXJUWJMOHNJ-UHFFFAOYSA-N 0.000 claims description 2
- CURNACMCPXDHAY-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoyl-phenylmethoxyamino]propanoate Chemical compound C=1C(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C(F)C=C(Cl)C=1OC(C)C(=O)N(CCC(=O)OC)OCC1=CC=CC=C1 CURNACMCPXDHAY-UHFFFAOYSA-N 0.000 claims description 2
- YMFVFVOTHNWMGV-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]-2-methylpropanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCC(C)C(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F YMFVFVOTHNWMGV-UHFFFAOYSA-N 0.000 claims description 2
- XHEOEOFOTNIAST-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]-4-fluorobutanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NC(CF)CC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F XHEOEOFOTNIAST-UHFFFAOYSA-N 0.000 claims description 2
- KFFXOHSSTZILMO-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]butanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NC(C)CC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F KFFXOHSSTZILMO-UHFFFAOYSA-N 0.000 claims description 2
- ADDWUOQORSWHDM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F ADDWUOQORSWHDM-UHFFFAOYSA-N 0.000 claims description 2
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 claims description 2
- BABMGUKATPIXFG-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfonylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(S(=O)(=O)C(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F BABMGUKATPIXFG-UHFFFAOYSA-N 0.000 claims description 2
- LYAKZIWJICXYGP-UHFFFAOYSA-N methyl 3-[2-[2-cyano-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(C#N)C(OC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F LYAKZIWJICXYGP-UHFFFAOYSA-N 0.000 claims description 2
- MUGDVHIVUPCEKQ-UHFFFAOYSA-N methyl 3-[[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]acetyl]-methylamino]propanoate Chemical compound C1=C(Cl)C(OCC(=O)N(C)CCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F MUGDVHIVUPCEKQ-UHFFFAOYSA-N 0.000 claims description 2
- AWXAVKPTARSLJU-UHFFFAOYSA-N methyl 3-[[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]acetyl]amino]propanoate Chemical compound C1=C(Cl)C(OCC(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F AWXAVKPTARSLJU-UHFFFAOYSA-N 0.000 claims description 2
- ZRWVFGFPSFFABT-UHFFFAOYSA-N methyl 4-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]butanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F ZRWVFGFPSFFABT-UHFFFAOYSA-N 0.000 claims description 2
- JSLXXPQGDGXWKL-UHFFFAOYSA-N methyl 5-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]pentanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F JSLXXPQGDGXWKL-UHFFFAOYSA-N 0.000 claims description 2
- QOPCLKLEMVHYIA-UHFFFAOYSA-N propyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenoxy]propanoylamino]propanoate Chemical compound C1=C(Cl)C(OC(C)C(=O)NCCC(=O)OCCC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QOPCLKLEMVHYIA-UHFFFAOYSA-N 0.000 claims description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
- 239000008394 flocculating agent Substances 0.000 claims 1
- 230000029553 photosynthesis Effects 0.000 claims 1
- 238000010672 photosynthesis Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 244000025254 Cannabis sativa Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 235000001014 amino acid Nutrition 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 238000006297 dehydration reaction Methods 0.000 description 10
- 239000002994 raw material Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
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- 239000008096 xylene Substances 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Definitions
- the present invention relates to a novel uracil compound, a preparation method thereof, and a herbicide comprising the same.
- weed control is very important for improving agricultural productivity, and various kinds of herbicides have been used.
- Triazine herbicides such as Atrazine, or anilide herbicides such as Alachlor or Metolachlor have been used in corn cultivation. Meanwhile, as non-selective herbicides, herbicides such as para R (Paraquat) or glyphosate have been used.
- Japanese Patent Laid-Open No. 2000-302,764 discloses a compound represented by the following formula (A).
- R 1 is a hydrogen atom or a substituted alkyl group
- R 2 is an alkyl group, an alkenyl group, or an alkynyl group
- R 3 is a hydrogen atom or a methyl group.
- Japanese Patent Laid-Open No. 2001-172,265 discloses a compound represented by the following general formula (B).
- R1 is a hydrogen atom or a substituted alkyl group
- R2 is a hydrogen atom or an alkyl group
- R3 is a hydrogen atom or a methyl group.
- R1 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, or the like
- R2 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, a phenyl group, a benzyl group, an alkoxy group, an alkylsulfonyl group And so on.
- the compound represented by the formula (A), (B), or (C) is a non-selective herbicide in orchards and non-cultivated lands due to the nature of the drug, which requires high dose treatment for controlling a large number of problem weeds, and when used as a selective herbicide. It is a situation that requires the development of high-performance drugs that can solve these problems because it is weak.
- Another object of the present invention is to provide a herbicide comprising as an active ingredient a compound selected from the above-described uracil compound and an agriculturally acceptable salt thereof, or a mixture thereof.
- Another object of the present invention is to provide a method for preparing the uracil compound.
- the present invention is characterized by the uracil compound represented by the following formula (1), or an agriculturally acceptable salt thereof.
- R1 and R2 are the same as or different from each other and represent a hydrogen atom or a C1 to C6 alkyl group
- R3 is a hydrogen atom, a hydroxyl group, a C1-C6 alkyl group, a C2-C6 alkenyl group, a C2-C6 alkynyl group, a C1-C8 alkoxy group, a C1-C6 haloalkyl group, a C2-C6 haloalkenyl group, a C1-C6 alkoxy C1 A C6 alkyl group or a C6 to C10 aryl C1 to C6 alkoxy group
- R4 represents a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, or a C1-C6 alkoxycarbonyl C1-C6 alkyl group
- R5 is a hydrogen atom, a C1-C6 alkyl group,
- the uracil-based compound represented by Chemical Formula 1 which is characterized by the present invention, exhibits a wide range of herbicidal effects from broadleaf weeds as well as flowering and weeds at low concentration. Thus, it is very useful as a non-selective herbicide for foliage treatment in orchards and non-cropland.
- the uracil-based compound represented by Chemical Formula 1 which is characterized by the present invention, does not harm harmful crops such as wheat and corn during soil treatment, and has a high selective herbicidal activity, which shows very excellent herbicidal activity against broadleaf, flowering and weeds. Effect.
- the herbicides of the present invention are very useful as herbicides suitable for use in cropland, orchards and non-cropland.
- the uracil compound represented by Chemical Formula 1 includes an agrochemically acceptable salt, racemate, single enantiomer or diastereomeric compound of the compound represented by Chemical Formula 1.
- uracil compound represented by Chemical Formula 1 may be used in the form of an agriculturally acceptable salt.
- Agrochemically acceptable salts may include, for example, metal salts, salts with organic bases, salts with inorganic acids, salts with organic acids, salts with basic or acidic amino acids, and the like.
- Suitable metal salts include, for example, alkali metal salts such as sodium salts, potassium salts and the like; Alkaline earth metal salts such as calcium salts, magnesium salts, barium salts, and the like; Aluminum salts and the like.
- Salts with organic bases are, for example, trimethylamine, triethylamine, pyridine, picoline, 2,6-lutidine, ethanolamine, diethanolamine, triethanolamine, cyclohexylamine, dicyclohexylamine, N Salts with, N-dibenzylethylenediamine and the like.
- Salts with inorganic acids may include, for example, salts with hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid and the like.
- Salts with organic acids may include, for example, salts with formic acid, acetic acid, trifluoroacetic acid, phthalic acid, fumaric acid, oxalic acid, tartaric acid, maleic acid, citric acid, succinic acid, methanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, and the like.
- Salts with basic amino acids may include, for example, salts with arginine, lysine, ornithine and the like.
- Salts with acidic amino acids may include, for example, salts with aspartic acid, glutamic acid and the like.
- R1 and R2 are the same or different and represent a hydrogen atom or a methyl group
- R3 represents a hydrogen atom, a hydroxyl group, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group, vinyl group, allyl group, methoxy group, ethoxy group, n-propoxy group , n-butoxy group, tert-butoxy group, chloromethyl group, dichloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, or benzyloxy group
- R4 represents a hydrogen atom, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, or tert-butyl group
- R5 is hydrogen atom, hydroxy group
- R1 and R2 represent the same or different hydrogen atoms or methyl groups
- R3 represents a hydrogen atom, a hydroxyl group, a methyl group, a methoxy group, or a benzyloxy group
- R4 represents a hydrogen atom or a methyl group
- R5 represents a hydrogen atom, a methyl group, an ethyl group, n-propyl group, n-butyl group, methoxy group, allyl group, propazyl group, benzyl group, benzyloxy group, or methoxycarbonylmethyl group
- X represents O, S, SO 2, or NH
- Y represents CH2, CH (CH3), CH2CH2, CH2CH2CH2, or CH (CH2F)
- W represents O, or NH
- Z is a uracil compound representing a chloro atom, a cyano group, or CSNH 2.
- R1 and R2 are the same as or different from each other and represent a hydrogen atom or a methyl group
- R 3 represents a hydrogen atom, a hydroxyl group, a methyl group, or a methoxy group
- R4 represents a hydrogen atom
- R5 represents a hydrogen atom, a methyl group, an ethyl group, n-butyl group, allyl group, propazyl group or CH2CO2CH3
- X represents O, S, or NH
- Y represents CH2, CH2CH2, or CH (CH2F)
- W represents O
- Z is a uracil compound representing a chloro atom.
- the present invention includes a method for producing a uracil compound represented by the formula (1).
- the carboxylic acid compound represented by the following Chemical Formula 2 is reacted with a chlorination reagent to prepare carboxylic acid chloride, and then the obtained carboxylic acid chloride is represented by the following Chemical Formula 3. It is a method of obtaining the uracil type compound represented by the said General formula (1) by making it react with an ester compound.
- R1, R2, R3, R4, R5, X, Y, Z, and W are as defined in Formula 1, respectively.
- the amino acid ester compound represented by the formula (3) is a commercially available compound, a known compound, or a person skilled in the art can be easily prepared using known methods.
- the chlorination reagent used in Scheme 1 is a conventional chlorination reagent that has been generally used, specifically, thionyl chloride, phosgene, phosphoryl oxychloride, oxaryl chloride, phosphorus trichloride, phosphorus pentachloride, and the like.
- the chlorination reaction can be carried out in a solvent or can be carried out without a solvent.
- the reaction solvent that can be used in the solvent can be used as long as it is a conventional organic solvent used in the art, specifically, dichloromethane, chloroform, dichloroethane, ethyl acetate, cyclohexane, benzene, chlorobenzene, toluene, Tetrahydrofuran, diisopropyl ether, 1,4-dioxane and the like can be used.
- the chlorination reagent is preferably used in an excess of 1 mole or more with respect to 1 mole of the carboxylic acid compound represented by Formula 2, and performs the reaction in the range of 20 ° C to 150 ° C.
- the reaction solution is concentrated under reduced pressure, dissolved in a solvent and reacted with the amino acid ester compound represented by the formula (3).
- the reaction is preferably performed under basic conditions, and an organic base such as triethylamine, pyridine, or dimethylaniline, or an inorganic base such as Na 2 CO 3, K 2 CO 3, or Li 2 CO 3 may be used.
- the reaction temperature is preferably in the range of 0 ° C to 100 ° C.
- the amount of the amino acid ester compound represented by Chemical Formula 3 may vary depending on whether the base is used.
- R1, R2, R3, R4, R5, X, Y, Z, and W are each as defined in Chemical Formula 1.
- the dehydrating agent used in Scheme 2 is a dehydrating reagent commonly used in amide dehydration reaction, N, N-carbonyldiimidazole, N, N-cyclohexyl carbodiimide, N- (3-dimethylaminopropyl) -N '-Ethylcarbodiimide, and (benzotriazol-1-yl) -N, N, N', N'-tetramethyluronium tetrafluoroborate and the like can be used, but not limited thereto.
- Dehydration reagent may be used in the range of 1 to 1.5 molar ratio with respect to 1 mole of the carboxylic acid compound represented by Formula 2.
- N, N-dimethylaminopyridine may be used as the catalyst, if necessary, and the catalyst may be used in a range of 0.05 to 0.1 mole ratio with respect to 1 mole of the carboxylic acid compound represented by Formula 2.
- the dehydration reaction may be carried out within a temperature range of 0 °C to 80 °C, preferably 20 °C to 50 °C.
- the reaction solvent all conventional organic solvents used in the art may be used. Specifically, dichloromethane, dichloroethane, ethyl acetate, acetonitrile, toluene, tetrahydrofuran, diethyl ether, dimethyl formamide, and the like may be used. Can be.
- the reaction mixture may be diluted in a general separation process, for example, diluted with an organic solvent, washed with an acidic aqueous solution, and then concentrated under reduced pressure, and purified by column chromatography if necessary.
- the compound represented by the following formula (4) is subjected to a nucleophilic substitution reaction with the compound represented by the following formula (5) under basic conditions, and the uracil represented by the above formula (1). It is a method of obtaining a system compound.
- R1, R2, R3, R4, R5, X, Y, Z, and W are as defined in Formula 1
- L is a leaving group (-OMs) as a leaving group (leaving group) , p-toluenesulfonate groups (-OTs), halogen atoms (e.g., Cl, Br) and the like.
- reaction solvents all conventional organic solvents used in the art as reaction solvents may be used, specifically, dichloromethane, chloroform, dichloroethane, ethyl acetate, cyclohexane, benzene, chlorobenzene, Toluene, cyclohexane, tetrahydrofuran, diisopropyl ether, 1,4-dioxane, acetonitrile and the like can be used.
- the base that can be used for the nucleophilic substitution reaction is an organic base such as triethylamine, pyridine, or dimethylaniline, or an inorganic base such as NaHCO 3, KHCO 3, Na 2 CO 3, K 2 CO 3, or Li 2 CO 3.
- the base used at this time is preferably used in the range of 1 to 1.1 moles with respect to 1 mole of the compound represented by the formula (5).
- the nucleophilic substitution reaction is carried out in the range of 0 °C to 100 °C.
- the compound represented by Chemical Formula 5 used as a raw material in the nucleophilic substitution reaction according to Scheme 3 may be prepared and used by the following Scheme 4 and Scheme 5.
- the carboxylic acid compound represented by the following Chemical Formula 6 is chlorinated by a conventional method using a chlorination reagent, and then reacted by adding an amino acid ester compound represented by the following Chemical Formula 3 to the reactants.
- an amino acid ester compound represented by the following Chemical Formula 3 is added to the reactants.
- R1, R2, R3, R4, R5, Y, and W are as defined in Formula 1
- L is a leaving group (methanesulfonate group (-OMs), p-toluenesulfo Nate groups (-OTs), halogen atoms (for example, Cl, Br), etc. are shown.
- the chlorination reagent in Scheme 5 may be selected from the reagents used in the chlorination reaction according to Scheme 1, and is preferably used in an excess of 1 mol or more with respect to 1 mol of the carboxylic acid compound represented by Formula 6 above.
- the reaction solution is concentrated under reduced pressure, dissolved in a solvent, and then reacted with the amino acid ester compound represented by Chemical Formula 3.
- the reaction is preferably performed under basic conditions, and an organic base such as triethylamine, pyridine, or dimethyl aniline, or an inorganic base such as Na 2 CO 3, K 2 CO 3, or Li 2 CO 3 may be used.
- the reaction temperature is preferably in the range of 0 ° C to 100 ° C.
- the amount of the amino acid ester compound represented by Chemical Formula 3 may vary depending on whether the base is used.
- Another method for preparing a compound represented by Chemical Formula 5 used as a raw material in a nucleophilic substitution reaction according to Scheme 3 may be a carboxylic acid compound represented by Chemical Formula 6, and Chemical Formula 3, as shown in Scheme 5 below.
- R1, R2, R3, R4, R5, Y, and W are as defined in Formula 1, L is a leaving group (methanesulfonate group (-OMs), p-toluenesulfonate Group (-OTs), halogen atoms (e.g., Cl, Br) and the like.
- -OMs methanesulfonate group
- -OTs p-toluenesulfonate Group
- halogen atoms e.g., Cl, Br
- the dehydrating agent used in Scheme 5 is a dehydrating reagent commonly used in amide dehydration reactions.
- N, N-carbonyldiimidazole, N, N-cyclohexyl carbodiimide, N- (3-dimethylaminopropyl) -N '-Ethylcarbodiimide, and (benzotriazol-1-yl) -N, N, N', N'-tetramethyluronium tetrafluoroborate and the like can be used, but not limited thereto.
- the dehydration reagent may be used in the range of 1 to 1.5 moles based on 1 mole of the carboxylic acid compound represented by Chemical Formula 6.
- N, N-dimethylaminopyridine may be used as the catalyst, if necessary.
- the catalyst may be used in the range of 0.05 to 0.1 mole ratio with respect to 1 mole of the carboxylic acid compound represented by the formula (6).
- the dehydration reaction may be carried out within a temperature range of 0 °C to 80 °C, preferably 20 °C to 50 °C.
- As the reaction solvent all conventional organic solvents used in the art may be used. Specifically, dichloromethane, dichloroethane, ethyl acetate, acetonitrile, toluene, tetrahydrofuran, diethyl ether, dimethylformamide, and the like may be used. Can be.
- the reaction mixture may be diluted with a general separation process, for example, diluted with an organic solvent, washed with an acidic aqueous solution, and then concentrated under reduced pressure, and purified by column chromatography if necessary.
- R1, R2, R3, R4, R5, Y, Z, and W are as defined in Formula 1, and n is an integer of 1 or 2 as the number of oxygen atoms (O).
- the oxidation reaction shown in Scheme 6 may be applied to the method disclosed in Phosphorus, Sulfur and Silicon and the Related Elements; English; 45; 1989; 31-34; Synthesis; English; 7; 1997; 787-791. .
- Oxone MCPBA, H2O2, KMnO4, NaIO4, t-BuOCl, Ca (OCl) 2, NaClO2, Sodium hyperchloride (NaOCl), Dioxane, Nitrous acid (HNO3), Ceric ammonium nitrate (ceric ammonium nitrate) can be used.
- R1, R2, R3, R4, R5, X, Y, and W are as defined in Chemical Formula 1.
- R1, R2, R3, R4, R5, X, Y, and W are as defined in Formula 1.
- the reaction mixture was washed with water, dried over magnesium sulfate and concentrated.
- the concentrated solution was separated and purified by silica gel column chromatography to obtain 24 g of the target substance containing a small amount of impurities. This was recrystallized twice with a mixed solvent of ethyl acetate and hexane to obtain 18.2 g of the target substance.
- the uracil compound represented by Chemical Formula 1 of the present invention may be usefully used as a herbicide, and when used as a herbicide, additives such as diluents, surfactants, dispersants, and auxiliary agents commonly used in the formulation of pesticides may be used.
- additives such as diluents, surfactants, dispersants, and auxiliary agents commonly used in the formulation of pesticides may be used.
- a compound can be formulated into various forms, such as a hydrating agent, an emulsion, a powder suspension, and a liquid, and can be used. These formulations can be used directly and can be processed by dilution in appropriate media.
- the spray volume can be used from several hundred liters to several thousand liters per hectare.
- the herbicide composition characterized by the present invention comprises 0.1% to 99.9% by weight of a compound selected from the uracil compound represented by the formula (1) and agrochemically acceptable salts thereof, or a mixture thereof, a surfactant, a solid or liquid diluent, 0.1 wt% to 99.9 wt% of an additive selected from dispersants and auxiliaries.
- the herbicide composition characterized by the present invention is formulated into a hydrating agent, a suspending agent, an emulsion, an emulsifying agent, a suspending agent, a liquid preparation, a dispersible liquid preparation, a granular water-forming agent, a granule, a powder, a liquid water-forming agent, a granular water-forming agent, a sleep-injured granule or a tablet.
- a hydrating agent a suspending agent, an emulsion, an emulsifying agent, a suspending agent, a liquid preparation, a dispersible liquid preparation, a granular water-forming agent, a granule, a powder, a liquid water-forming agent, a granular water-forming agent, a sleep-injured granule or a tablet.
- Table 2 below is a representative composition of the herbicide composition of the present invention, the herbicide composition of the present invention is not limited thereto.
- the surfactant used in the present invention is a substance having a high surface activity and is an amphiphilic substance having hydrophilic and lipophilic molecular groups in a molecule, and has a detergency, dispersing ability, emulsifying power, solubilizing power, wetting power, bactericidal power, foaming power, and penetration power. It is excellent in, etc., and acts to wet, collapse, disperse, and emulsify to effectively express the drug.
- the ratio of the active ingredient may be adjusted according to the use, and it is sometimes necessary to use a larger ratio of the surfactant than the active ingredient, and may be added in preparation or used in tank mixing.
- Diluents used in the present invention can be classified into solid diluents and liquid diluents depending on their properties. Highly absorbent diluents as solid diluents are particularly good when making hydrates.
- the liquid diluent and the solvent are preferably stable without phase separation even at 0 ° C.
- Liquid diluents include water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chloro Benzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl Ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N, N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzo
- Solid diluents include talc, titanium dioxide, feldspar clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husk, wholemeal, soybean flour, pumice, wood flour, walnut husk, Lignin and the like can be used.
- the method of making the composition is a conventional method, and the liquid preparation only needs to mix the components, and the fine solid composition may be mixed and ground in a hammer or a flow mill.
- Suspensions can be prepared by admixing in a wet mill and granules can be prepared by spraying an active substance onto the granular carrier.
- the following components were thoroughly mixed and the liquid surfactant was mixed while spraying onto the solid components. Grinding in a hammer mill brought the particle size to 100 ⁇ m or less.
- Methylnaphthalene 35% by weight
- the formulation of the present invention was sprayed by diluting to an appropriate concentration in actual use.
- the uracil compounds according to the present invention are very useful as non-selective foliage treatment herbicides for orchards and non-cultivated lands because they exhibit broad herbicidal effects not only on grasses and weeds but also broadleaf weeds by foliage treatment at low concentrations.
- the uracil compound according to the present invention is particularly useful as a herbicide for soil treatment in corn and wheat farming because it exhibits high selectivity for cultivated crops such as corn and wheat during soil treatment.
- the herbicide composition of the present invention can be used up to 10 g to 1 kg per hectare (ha) based on the active ingredient, preferably 10 g to 400 g.
- the choice of dosage is determined by factors such as weed generation, growth level, and preparation.
- the herbicide composition of the present invention may be used in addition to the compound of the general formula (1) as an active ingredient with a conventional active ingredient having activity as a pesticide.
- active ingredients that can be used together in the herbicide compositions of the invention include acetyl-CoA carboxylase inhibitors (ACC), acetolactate synthase inhibitors (ALS), amides, auxin herbicides, auxin transport inhibitors, carotenoid biosynthesis inhibitors, Nolpyrubilshikimate 3-phosphate synthase inhibitors (ESPS), glutamine synthetase inhibitors, lipid biosynthesis inhibitors, mitosis inhibitors, protoporpynogen IX oxidase inhibitors, photosynthetic inhibitors, synergists, growth agents, cell wall biosynthesis inhibitors, and It is also useful to use in admixture with one or more herbicidally active compounds selected from the group consisting of other herbicides.
- ACC acetyl-CoA carboxylase inhibitors
- ALS
- acetyl-CoA carboxylase inhibitor is a cyclohexenone oxime ether, alkoxydim, cletodim, cloproxidim, cycloxydim, cetoxydim, tralcoxydim, butoxyldim, clepoxydim, Or as tetraphyloxydim, phenoxyphenoxypropionic acid ester, metamipop, sihalofop-butyl, diclofo-methyl, phenoxaprop-ethyl, phenoxaprop-P-ethyl, pentiaprop- Ethyl, Fluazifop-Butyl, Fluazifop-P-Butyl, Haloxifop-Ethoxyethyl, Haloxifop-Methyl, Haloxifop-P-Methyl, Isoxapyrifop, Propacquisapop, Quiz Allopop-ethyl, quiz
- acetolactate synthase inhibitor is an imidazolinone as imazapyr, imazaquin, imazamethabenz-methyl, imaco, imazapic, imazetapyr, or imazametapyr, as pyrimidyl ether Pyrithiobac-acid, pyrithiobac-sodium, bispyribac-sodium, or pyribenzoxime, florasullam, flumetsulam, or metosullam as sulfonamide, amidosulfuron, azimsulfuron, benzulfur as sulfonylurea Furon-methyl, chlorimuron-ethyl, chlorsulfuron, cynosulfuron, cyclosulfuron, etamethsulfuron-methyl, ethoxysulfuron, plazasulfuron, halosulfuron-methyl, imazosulfuron, metsulfuron -Meth
- auxin herbicide clopyralide or picloram, 2,4-D, or benazolin may be used as the pyridine carboxylic acid.
- Naphthalam, or diflufenzopyr may be used as the auxin transport inhibitor, and the carotenoid biosynthesis inhibitor may be benzophenaf, clomazone, diflufenican, fluorochloridone, flulidone, pyrazolinate, Pyrazoxifen, isoxaplutol, isoxaclortol, mesotrione, sulcotrione (chlormethulon), ketospiradox, flutamone, norflurazone, or amitrol can be used.
- the carotenoid biosynthesis inhibitor may benzophenaf, clomazone, diflufenican, fluorochloridone, flulidone, pyrazolinate, Pyrazoxifen, isoxaplutol, isoxaclortol, mesotrione, sulcotrione (chlormethulon), ketospiradox, flutamone, norflurazone, or amitrol can be used.
- Glyphosate or sulfosate, may be used as the enolpyrubilicimate 3-phosphate synthase inhibitor (ESPS), and villanafos (non-alphafos), or glufosinate-ammonium may be used as the glutamine synthetase inhibitor. Can be used.
- EPS enolpyrubilicimate 3-phosphate synthase inhibitor
- villanafos non-alphafos
- glufosinate-ammonium may be used as the glutamine synthetase inhibitor.
- the lipid biosynthesis inhibitors include anilophos as anilide or mefenacet, dimethenamid as chloroacetanilide, S-dimethenamid, acetochlor, alachlor, butachlor, buteneaclor, dietathyl-ethyl, di Methachlor, metazachlor, methol achlor, S-methol achlor, pretyl achlor, propacchlor, priaclor, terbuchlor, tenylchlor, or xyl achlor, butylate as thiourea, cycloate, Di-acrylate, dimepiperate, EPTC, esprocarb, molinate, pebulate, prosulfocarb, thiobencarb (benthiocarb), tri-acrylate, or benolate, benfurate, Or perfluidone can be used.
- mitosis inhibitors include asulam as carbamate, carbetamid, chlorprofam, orbencarb, pronamide (propizamide), profam, or thiocarbazil, benipine as dinitroaniline, butot Raline, dinitramine, etafluralline, fluchlorinline, oryzaline, pendimethalin, prodiamine, or trituraline, dithiopyr as pyridine, or thiazopyr, butamifos, chlortal-dimethyl (DCPA ), Or maleic acid hydrazide can be used.
- the protoporpynogen IX oxidase inhibitors are diphenyl ethers such as asifluorfen, asifluorophene-sodium, acloniphene, biphenox, chlornitropen (CNP), ethoxyphene, fluorodiphene, fluoroglycopene Ethyl, pomesaphene, furyloxyphene, lactofen, nitrophene, nitrofluorophene, or oxyfluorene, oxadiargyl as oxadiazole, or azaphenidine, butafen as oxadione, cyclic imide Acyl, carfentrazone-ethyl, cinidon-ethyl, flumiclolac-pentyl, flumioxazine, flumipropine, flupropacyl, fluthiacet-methyl, sulfentrazone, or thidiazimine, pyrazole Pilaflu
- the photosynthetic inhibitor is selected from propanyl, pyridate pyridafol, benzothiadiazinone, betazone, bromophenoxime, dinocept, dinocept-acetate, dinoterb, or DNOC, dipyridylene as dinitrophenol.
- Perquat-chloride dipenzoquat-methylsulfate, diquat, or paraquat-dichloride, chlorbromuron, chlorotoluron, diphenoxalone, dimefuron, diuron, etidimuron, phenuron, fluorine as urea Meturon, isoproturon, isouron, linuron, metabenzthiazuron, metazole, methopenzuron, methoxuron, monolinuron, neburon, siduron, or tebutiuron, bromocinyl as phenol, Or as oxynyl, chloridazone, triazine, amethrin, atrazine, cyanazine, desmethrin, dimethamethrin, hexazinone, promethone, promethrin, propazine, simazine, cymetrin, ter Boomerone, Terbutrin,
- Tridiphan may be used as the oxirane as the synergist, and 2,4-DB, clomeprop, dichlorprop, dichlorprop-P (2,4) as aryloxyalkanoic acid as the growth material.
- -DP-P fluorooxypyr
- MCPA mecoprop
- mecoprop-P or triclopyr
- chlorambene as benzoic acid
- dicamba quinclolac as quinolinecarboxylic acid
- the other herbicides include Dalapone as dichloropropionic acid, etofumesate as dihydrobenzofuran, chlorfenac (phenac) as phenylacetic acid, or aziprotrin, barban, bensulfide, benzthiazuron, benzofluorine, bumina Phos, butidazole, buturon, carfenstrol, chlorbufam, chlorfenprop-methyl, chloroxalon, cinnamline, cumyluron, cyclluron, ciprazin, ciprazole, dibenzyluron, dipropertrin , Dimrone, eglinazine-ethyl, endortal, ethiozin, flucarbazone, fluorbentranil, flupoxam, isocarbamide, isopropaniline, carbutylate, mefluidide, monuron, napropamide , Napropanylide, nitraline, o
- the compounds according to the invention have significant herbicidal activity against harmful plants of monocotyledons (flowers and weeds), and dicotyledons (broadleaf weeds). Specifically, some representative examples of weed plants that can be controlled by the compounds according to the present invention are mentioned, but are not limited to specific species.
- weed species that may be weeded by the herbicide of the present invention are as follows.
- Flower and weed (monolithic weed) species include barley, wheat, blood, American dog breeze, scabbard, king blue grass, dog grass, pulp grass, fall pulp grass, dredge, vine, large bean, larva, poa grass, wangpo grass Can be selected.
- the broad-leaved weeds (bicotyledonous) species include the herbaceous weeds represented by Bangdongsaeng, Geumbangdongsa, Hyangbuja, Beethoven dongsa, Feces, Olgae, barberry; Nasturtium, hairy younger, creeper grass, wormwood hatch, mugwort, American fern, western dandelion, mangosteen, forget-me-not, hairy starfish, locust, barley grass, evergreen mugwort, goblin needle, jindeukchak, maple leaf ragweed, moth, alveolus, king Chrysanthemum weeds, such as horsetail, American mugwort, squirrel, dandelion, ragweed, fat, and red sprout; Larvae and weeds such as nectar and weeds such as scented oil, persimmon grass, perilla grass, motherwort, sesame grass, big grass bed, and baby green bed; Hyunsam and weeds, such
- test agent was dissolved in a mixture of 1 part by weight of the test agent, 5 parts by weight of acetone, and 1 part by weight of an emulsifier, and diluted with water to prepare a hydrating agent sprayed at a rate of 2000 L per hectare.
- the amount of active compound was chosen to be the specific amount desired.
- weeding activity for each plant was 0 (uncontrolled) to 100 (Complete control) and crops were evaluated according to the 0 (harmless) to 10 (completely tested) grade table and evaluated as the control price for the untreated areas.
- control compound is a compound shown in Japanese Patent Laid-Open Nos. 2000-302764 and 2001-172,265, whose structural formula is as follows.
- control compounds 1, 2 and 3 have herbicidal activity against the larvae but are not perfect, and the herbicidal activity against monocotyledonous weeds is extremely low. shall.
- the compound represented by the formula (1) characterized by the present invention is an amide compound of the ⁇ -amino acid skeleton and exhibits a broad range of herbicidal activity against flowering plants, weeds (monolithic plants), and broadleaf weeds (dicotyledonous plants) during foliage treatment It was found to be useful as a non-selective herbicide for the treatment of foliage, and when treated with soil, it was found to be useful as a selective herbicide for crop cultivation because of its excellent herbicidal activity against the cultivars and broadleaf weeds.
- the compound represented by Chemical Formula 1 of the present invention is expected to have an effect of solving the problem of environmental pollution by greatly reducing the dosage as a high-performance herbicide.
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Abstract
Description
Claims (13)
- 하기 화학식 1로 표시되는 우라실계 화합물 및 이의 농약학적으로 허용 가능한 염으로부터 선택된 화합물 :[화학식1]상기 화학식 1에서,R1, 및 R2는 서로 같거나 다른 것으로 수소원자, 또는 C1~C6 알킬기를 나타내며;R3은 수소원자, 하이드록시기, C1~C6 알킬기, C2~C6 알케닐기, C2~C6 알키닐기, C1~C8 알콕시기, C1~C6 할로알킬기, C2~C6 할로알케닐기, C1~C6 알콕시 C1~C6 알킬기, 또는 C6~C10 아릴 C1~C6 알콕시기를 나타내며;R4는 수소원자, C1~C6의 알킬기, C1~C6의 할로알킬기, 또는 C1~C6 알콕시카르보닐 C1~C6 알킬기를 나타내며;R5는 수소원자, C1~C6 알킬기, C1~C6 알콕시기, C2~C6 할로알킬기, C2~C6 알케닐기, C2~C6 할로알케닐기, C2~C6 알키닐기, C1~C6 알콕시카르보닐 C1~C6 알킬기, C6~C10 아릴 C1~C6 알킬기, C6~C10 아릴 C1~C6 알콕시기를 나타내며;X는 O, S, SO, SO2, NH, 또는 N(C1~C6 알킬)를 나타내며;Y는 C1~C6 알킬렌기, 또는 C1~C6 할로알킬렌기를 나타내며;W는 O, S, NH, 또는 N(C1~C6 알킬)를 나타내며;Z는 할로겐원자, 시아노기, CONH2, 또는 CSNH2를 나타낸다.
- 청구항 1에 있어서,상기 R1, 및 R2는 서로 같거나 다른 것으로 수소원자, 또는 메틸기를 나타내며;상기 R3은 수소원자, 하이드록시기, 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, 비닐기, 알릴기, 메톡시기, 에톡시기, n-프로폭시기, n-부톡시기, tert-부톡시기, 클로로메틸기, 디클로로메틸기, 플루오로메틸기, 디플루오로메틸기, 트리플루오로메틸기, 또는 벤질옥시기를 나타내며;상기 R4는 수소원자, 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, 또는 tert-부틸기를 나타내며;상기 R5는 수소원자, 하이드록시기, 메틸기, 에틸기, n-프로필기, 이소프로필기, n-부틸기, tert-부틸기, 비닐기, 알릴기, 프로파질기, 메톡시기, 에톡시기, n-프로폭시기, n-부톡시기, tert-부톡시기, 벤질기, 펜에틸기, 메톡시카르보닐메틸기, 메톡시카르보닐에틸기, 메톡시카르보닐프로필기, 에톡시카르보닐메틸기, 벤질옥시기, 또는 펜에틸옥시기를 나타내며;상기 X는 O, S, SO2, NH, 또는 N(CH3)를 나타내며;상기 Y는 CH2, CH(CH3), CH2CH2, CH2CH2CH2, CH(CF3), CH(CH2F), CH(CHF2), CH2CHF, 또는 CH2CF2를 나타내며;상기 W는 O, NH, 또는 N(CH3)를 나타내며;상기 Z는 클로로원자, 시아노기, CONH2, 또는 CSNH2를 나타내는 것을 특징으로 하는 화합물.
- 청구항 1에 있어서,상기 R1, 및 R2는 서로 같거나 다른 것으로 수소원자, 또는 메틸기를 나타내며;상기 R3은 수소원자, 하이드록시기, 메틸기, 메톡시기, 또는 벤질옥시기를 나타내며;상기 R4는 수소원자, 또는 메틸기를 나타내며;상기 R5는 수소원자, 메틸기, 에틸기, n-프로필기, n-부틸기, 메톡시기, 알릴기, 프로파질기, 벤질기, 벤질옥시기, 또는 메톡시카르보닐메틸기를 나타내며;상기 X는 O, S, SO2, 또는 NH를 나타내며;상기 Y는 CH2, CH(CH3), CH2CH2, CH2CH2CH2, 또는 CH(CH2F)를 나타내며;상기 W는 O, 또는 NH를 나타내며;상기 Z는 클로로원자, 시아노기, 또는 CSNH2를 나타내는 것을 특징으로 하는 화합물.
- 청구항 1에 있어서,3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 1);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}메톡시아미노]프로피온산 메틸에스테르(화합물번호 4);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}벤질옥시아미노]프로피온산 메틸에스테르(화합물번호 5);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}하이드록시아미노]프로피온산 메틸에스테르(화합물번호 6);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]-4-플루오로부티릭산 메틸에스테르(화합물번호 8);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]부티릭산 메틸에스테르(화합물번호 9);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]-2-메틸프로피온산 메틸에스테르(화합물번호 10);4-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]부티릭산 메틸에스테르(화합물번호 11);5-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]펜타노익산 메틸에스테르(화합물번호 12);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소에틸}아미노]프로피온산 메틸에스테르(화합물번호 13);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페닐아미노]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 15);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소에틸}메틸아미노]프로피온산 메틸에스테르(화합물번호 16);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소이소프로필}아미노]프로피온산 메틸에스테르(화합물번호 18);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 벤질에스테르(화합물번호 20);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 n-프로필에스테르(화합물번호 21);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피오닐옥시 아세트산 메틸에스테르(화합물번호 22);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 n-부틸에스테르(화합물번호 23);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 에틸에스테르(화합물번호 24);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 알릴에스테르(화합물번호 25);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 프로파질에스테르(화합물번호 26);4-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]부티릭산 에틸에스테르(화합물번호 28);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페닐티오]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 36);3-[{2-[2-시아노-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 46);3-[{2-[2-아미노티오카르보닐-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페녹시]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 52);3-[{2-[2-클로로-5-(3,6-다이하이드로-3-메틸-2,6-다이옥소-4-트리플루오로메틸-1(2H)-피리미디닐)-4-플루오로페닐술포닐]-1-옥소프로필}아미노]프로피온산 메틸에스테르(화합물번호 61); 및농약학적으로 허용 가능한 이들의 염으로부터 선택되는 화합물.
- 청구항 5에 있어서,화본과 잡초와 광엽 잡초 제거를 위한 경엽처리용 제초제.
- 청구항 5에 있어서,재배작물에 대한 선택성을 가지며, 화본과 잡초와 광엽 잡초 제거를 위한 토양처리용 제초제.
- 청구항 8에 있어서,수화제, 현탁제, 유제, 유탁제, 미탁제, 액제, 분산성 액제, 입상수화제, 입제, 분제, 액상수화제, 입상수화제, 수면부상성입제 또는 정제로 제제화된 것을 특징으로 하는 제초제 조성물.
- 청구항 8에 있어서,상기 활성성분은 아세틸-CoA 카르복실라제 억제제(ACC), 아세토락테이트 신타제 억제제(ALS), 아미드, 옥신 제초제, 옥신 수송 억제제, 카로테노이드 생합성 억제제, 에놀피루빌시키메이트 3-포스페이트 신타제 억제제(ESPS), 글루타민 신테타제 억제제, 지질 생합성 억제제, 유사분열 억제제, 프로토포르피리노겐 IX 옥시다제 억제제, 광합성 억제제, 상승작용제, 성장 물질, 세포벽 생합성 억제제, 및 공지 제초제로 이루어지는 군으로부터 선택되는 하나 또는 그 이상의 성분을 추가로 포함하는 것을 특징으로 하는 제초제 조성물.
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CN200980142137.8A CN102203071B (zh) | 2008-10-02 | 2009-09-24 | 尿嘧啶系化合物及包括其的除草剂 |
US13/122,199 US8193198B2 (en) | 2008-10-02 | 2009-09-24 | Uracil compounds and a herbicide comprising the same |
BRPI0913829-3A BRPI0913829B1 (pt) | 2008-10-02 | 2009-09-24 | Composto de uracil, herbicida, composição herbicida, e, método de preparação de um composto de uracil |
EP09817963.3A EP2343284B1 (en) | 2008-10-02 | 2009-09-24 | Uracil-based compounds, and herbicides comprising same |
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PL09817963T PL2343284T3 (pl) | 2008-10-02 | 2009-09-24 | Pochodne uracylu i herbicydy zawierające te pochodne |
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Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
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US20150024940A1 (en) * | 2012-04-12 | 2015-01-22 | Dongbu Farm Hannong Co., Ltd. | Herbicidal composition comprising uracil compound as active ingredient |
WO2018029029A1 (en) | 2016-08-09 | 2018-02-15 | Basf Se | Method for controlling ppo resistant weeds |
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WO2020172305A1 (en) | 2019-02-19 | 2020-08-27 | Gowan Company, L.L.C. | Stable liquid compositions and methods of using the same |
KR102236167B1 (ko) * | 2019-05-17 | 2021-04-05 | 주식회사 창발켐텍 | 3-(2-클로로프로피오닐아미노)프로피온산 알킬 에스테르 제조방법 |
WO2021151741A1 (en) | 2020-01-31 | 2021-08-05 | Basf Se | Herbicide combinations comprising glufosinate and tiafenacil |
RU2760474C1 (ru) * | 2020-10-01 | 2021-11-25 | Государственное бюджетное учреждение Республики Башкортостан "Научно-исследовательский технологический институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Академии наук Республики Башкортостан" | Гербицидная синергетическая композиция |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859229A (en) | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
JP2000302764A (ja) | 1999-04-26 | 2000-10-31 | Sumitomo Chem Co Ltd | フェニルウラシル化合物およびその用途 |
JP2001172265A (ja) | 1999-12-15 | 2001-06-26 | Sumitomo Chem Co Ltd | ヒドロキサム酸誘導体およびその用途 |
US6403534B1 (en) | 2000-06-28 | 2002-06-11 | Sumitomo Chemical Company, Limited | Uracil compounds and use thereof |
EP1272478A1 (de) | 2000-04-05 | 2003-01-08 | Bayer Aktiengesellschaft | Substituierte phenyluracile |
US6537948B1 (en) | 2000-02-04 | 2003-03-25 | Sumitomo Chemical Company, Limited | Uracil compounds and use thereof |
WO2003029226A1 (en) | 2001-09-26 | 2003-04-10 | Basf Aktiengesellschaft | Heterocyclyl substituted phenoxyalkyl-, phenylthioalkyl-, phenylaminoalkyl- and phenylalkyl-sulfamoylcarboxamides |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1194638A (zh) * | 1995-06-29 | 1998-09-30 | 拜尔公司 | 取代的氰基苯基尿嘧啶 |
AU701851B2 (en) * | 1995-06-29 | 1999-02-04 | Bayer Aktiengesellschaft | Substituted cyanophenyluracils |
JPH10291983A (ja) * | 1997-02-19 | 1998-11-04 | Sumitomo Chem Co Ltd | ピリダジン−3−オン誘導体およびその用途 |
PT1087664E (pt) * | 1998-06-16 | 2003-10-31 | Basf Ag | Misturas herbicidas com uma accao sinergica |
US8247563B2 (en) * | 2006-12-11 | 2012-08-21 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using indanone based cholinesterase inhibitors |
JP2008302764A (ja) * | 2007-06-06 | 2008-12-18 | Toyota Motor Corp | 体重検出装置 |
-
2009
- 2009-09-24 KR KR1020090090692A patent/KR101103840B1/ko active IP Right Grant
- 2009-09-24 AU AU2009300571A patent/AU2009300571B2/en active Active
- 2009-09-24 MY MYPI2011001470A patent/MY158047A/en unknown
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- 2009-09-24 US US13/122,199 patent/US8193198B2/en active Active
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- 2009-09-24 WO PCT/KR2009/005471 patent/WO2010038953A2/ko active Application Filing
- 2009-09-24 CA CA2739347A patent/CA2739347C/en active Active
-
2011
- 2011-03-25 CL CL2011000656A patent/CL2011000656A1/es unknown
- 2011-03-29 EC EC2011010924A patent/ECSP11010924A/es unknown
- 2011-03-31 CO CO11040012A patent/CO6362000A2/es active IP Right Grant
- 2011-04-06 CR CR20110183A patent/CR20110183A/es unknown
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4859229A (en) | 1986-07-31 | 1989-08-22 | Hoffmann-La Roche Inc. | 3-Aryluracils having an ether (thio) carbomyloxy or sulphomyloxy substituent on the aromatic moiety |
JP2000302764A (ja) | 1999-04-26 | 2000-10-31 | Sumitomo Chem Co Ltd | フェニルウラシル化合物およびその用途 |
JP2001172265A (ja) | 1999-12-15 | 2001-06-26 | Sumitomo Chem Co Ltd | ヒドロキサム酸誘導体およびその用途 |
US6537948B1 (en) | 2000-02-04 | 2003-03-25 | Sumitomo Chemical Company, Limited | Uracil compounds and use thereof |
EP1272478A1 (de) | 2000-04-05 | 2003-01-08 | Bayer Aktiengesellschaft | Substituierte phenyluracile |
US6403534B1 (en) | 2000-06-28 | 2002-06-11 | Sumitomo Chemical Company, Limited | Uracil compounds and use thereof |
WO2003029226A1 (en) | 2001-09-26 | 2003-04-10 | Basf Aktiengesellschaft | Heterocyclyl substituted phenoxyalkyl-, phenylthioalkyl-, phenylaminoalkyl- and phenylalkyl-sulfamoylcarboxamides |
Non-Patent Citations (4)
Title |
---|
JOURNAL OF CHEMICAL RESEARCH, vol. 12, 1985, pages 3830 - 3860 |
PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS, vol. 25, 1985, pages 297 - 306 |
PHOSPHORUS, SULFUR AND SILICON AND THE RELATED ELEMENTS, vol. 45, 1989, pages 31 - 34 |
SYNTHESIS, vol. 7, 1997, pages 787 - 791 |
Cited By (22)
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US20150024940A1 (en) * | 2012-04-12 | 2015-01-22 | Dongbu Farm Hannong Co., Ltd. | Herbicidal composition comprising uracil compound as active ingredient |
US10206399B2 (en) * | 2012-04-12 | 2019-02-19 | Dongbu Farm Hannong Co., Ltd. | Herbicidal composition comprising uracil compound as active ingredient |
WO2018029029A1 (en) | 2016-08-09 | 2018-02-15 | Basf Se | Method for controlling ppo resistant weeds |
US11723365B2 (en) | 2016-08-09 | 2023-08-15 | Basf Se | Method for controlling PPO resistant weeds |
US11274083B2 (en) | 2017-12-19 | 2022-03-15 | Syngenta Crop Protection Ag | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
WO2019121543A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2019121544A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
US11497212B2 (en) | 2017-12-19 | 2022-11-15 | Syngenta Crop Protection Ag | Substituted thiophenyl uracils, salts thereof and the use thereof as herbicidal agents |
WO2019121547A1 (de) | 2017-12-19 | 2019-06-27 | Bayer Aktiengesellschaft | Substituierte thiophenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2021013799A1 (de) | 2019-07-22 | 2021-01-28 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2021013800A1 (de) | 2019-07-22 | 2021-01-28 | Bayer Aktiengesellschaft | Substituierte n-phenyl-n-aminouracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2021018664A1 (en) | 2019-08-01 | 2021-02-04 | Basf Se | Herbicidal uracilpyridines |
WO2022043205A1 (de) | 2020-08-24 | 2022-03-03 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
EP4230621A1 (de) | 2022-02-22 | 2023-08-23 | Bayer AG | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
EP4230620A1 (de) | 2022-02-22 | 2023-08-23 | Bayer Aktiengesellschaft | Substituierte n-amino-n´-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2023161172A1 (de) | 2022-02-22 | 2023-08-31 | Bayer Aktiengesellschaft | Substituierte n-benzoesäureuracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2023222831A1 (en) | 2022-05-20 | 2023-11-23 | Syngenta Crop Protection Ag | Herbicidal compositions |
WO2023247976A1 (en) | 2022-06-24 | 2023-12-28 | Redag Crop Protection Ltd | Deuterated herbicides based on oxazinones and 6-(trifluoromethyl)pyrimidine-2,4-diones |
WO2024078906A1 (de) | 2022-10-10 | 2024-04-18 | Bayer Aktiengesellschaft | Substituierte n-phenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104954A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104952A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cyclopropyloxyphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
WO2024104956A1 (de) | 2022-11-16 | 2024-05-23 | Bayer Aktiengesellschaft | Substituierte cycloalkylsulfanylphenyluracile sowie deren salze und ihre verwendung als herbizide wirkstoffe |
Also Published As
Publication number | Publication date |
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CN102203071B (zh) | 2014-07-30 |
BRPI0913829B1 (pt) | 2018-02-06 |
EP2343284A2 (en) | 2011-07-13 |
PL2343284T3 (pl) | 2015-08-31 |
BRPI0913829A2 (pt) | 2016-07-26 |
MY158047A (en) | 2016-08-30 |
CR20110183A (es) | 2011-09-05 |
EP2343284B1 (en) | 2014-12-03 |
ECSP11010924A (es) | 2011-07-29 |
US8193198B2 (en) | 2012-06-05 |
KR101103840B1 (ko) | 2012-01-06 |
JP2012504599A (ja) | 2012-02-23 |
JP5291197B2 (ja) | 2013-09-18 |
AU2009300571A1 (en) | 2010-04-08 |
CN102203071A (zh) | 2011-09-28 |
EA201170524A1 (ru) | 2011-10-31 |
CA2739347A1 (en) | 2010-04-08 |
ES2530540T3 (es) | 2015-03-03 |
WO2010038953A3 (ko) | 2010-07-01 |
EA019009B1 (ru) | 2013-12-30 |
EP2343284A4 (en) | 2011-12-28 |
CA2739347C (en) | 2014-05-27 |
CO6362000A2 (es) | 2012-01-20 |
CL2011000656A1 (es) | 2011-08-19 |
AU2009300571B2 (en) | 2012-09-13 |
KR20100038052A (ko) | 2010-04-12 |
US20110224083A1 (en) | 2011-09-15 |
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