CN1225086A - Substituted aromatic carbonyl compounds and their derivatives - Google Patents
Substituted aromatic carbonyl compounds and their derivatives Download PDFInfo
- Publication number
- CN1225086A CN1225086A CN 97196302 CN97196302A CN1225086A CN 1225086 A CN1225086 A CN 1225086A CN 97196302 CN97196302 CN 97196302 CN 97196302 A CN97196302 A CN 97196302A CN 1225086 A CN1225086 A CN 1225086A
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- bases
- amino
- alkyl
- methyl
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- -1 aromatic carbonyl compounds Chemical class 0.000 title claims abstract description 210
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 35
- 229910052736 halogen Chemical group 0.000 claims abstract description 34
- 150000002367 halogens Chemical group 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000001301 oxygen Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 88
- 229910052801 chlorine Inorganic materials 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000011737 fluorine Substances 0.000 claims description 44
- 229910052731 fluorine Inorganic materials 0.000 claims description 44
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 42
- 239000005864 Sulphur Chemical group 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 241000196324 Embryophyta Species 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 13
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 229910001868 water Inorganic materials 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229950001891 iprotiazem Drugs 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 6
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- QOAMWZMAXNNNDC-UHFFFAOYSA-N 4-(1,2-thiazol-3-yl)oxadiazole Chemical compound S1C=CC(C=2N=NOC=2)=N1 QOAMWZMAXNNNDC-UHFFFAOYSA-N 0.000 claims description 2
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 2
- NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 2
- GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 2
- DWDAZFJBSZTCCM-UHFFFAOYSA-N [O]C1CCCCC1 Chemical compound [O]C1CCCCC1 DWDAZFJBSZTCCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000006309 butyl amino group Chemical group 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 2
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 18
- 241000405414 Rehmannia Species 0.000 claims 1
- 230000002508 compound effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 25
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 150000004702 methyl esters Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 244000025254 Cannabis sativa Species 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000975 dye Substances 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 239000011707 mineral Substances 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 230000001419 dependent effect Effects 0.000 description 4
- 230000008029 eradication Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000010902 straw Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000219144 Abutilon Species 0.000 description 3
- 241000219318 Amaranthus Species 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
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- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 235000014820 Galium aparine Nutrition 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
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- 150000002148 esters Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
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- IBXNCJKFFQIKKY-UHFFFAOYSA-N 1-pentyne Chemical compound CCCC#C IBXNCJKFFQIKKY-UHFFFAOYSA-N 0.000 description 2
- ABOOPXYCKNFDNJ-UHFFFAOYSA-N 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- RMFGNMMNUZWCRZ-UHFFFAOYSA-N Humulone Natural products CC(C)CC(=O)C1=C(O)C(O)(CC=C(C)C)C(O)=C(CC=C(C)C)C1=O RMFGNMMNUZWCRZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 244000017020 Ipomoea batatas Species 0.000 description 2
- 235000002678 Ipomoea batatas Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000209510 Liliopsida Species 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
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- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 description 1
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- ZTMKADLOSYKWCA-UHFFFAOYSA-N lenacil Chemical compound O=C1NC=2CCCC=2C(=O)N1C1CCCCC1 ZTMKADLOSYKWCA-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
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- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229940031815 mycocide Drugs 0.000 description 1
- QTGVGIVRLSGTJJ-UHFFFAOYSA-N n-(acetamidomethyl)-2-chloro-n-(2,6-diethylphenyl)acetamide Chemical compound CCC1=CC=CC(CC)=C1N(CNC(C)=O)C(=O)CCl QTGVGIVRLSGTJJ-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
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- 239000002420 orchard Substances 0.000 description 1
- 239000011146 organic particle Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
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- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-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
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 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
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Abstract
The invention relates to novel substituted aromatic carbonyl compounds of formula (I), preparation method thereof and appliance as herbicide, wherein Q represents oxygen, sulfur or imino (NH), R1 represents hydrogen or halogen, R<2> represnets following groups as A<1>, A<2>, A<3>, wherein A<1>, A<2>, A<3> are defined as description.
Description
The present invention relates to the aromatic carbonyl compounds and the derivative thereof of novel substituted, its preparation method and its are as herbicide applications.
Some aromatic carbonyl compounds with replacement of the heterocyclic radical group that connects through nitrogen be known (referring to, DE-2102848, DE-2119260, DE-2166456, DE-2342934).Yet, the weeding activity of unexposed these compounds still.
Therefore, the invention provides the aromatic carbonyl compounds and the derivative thereof of the replacement of novel logical formula I
Wherein Q represents oxygen, sulphur or imino-(NH), R
1Represent hydrogen or halogen, R
2Represent following radicals
-A
1-A
2-A
3
Wherein
A
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-,
R wherein
4Represent hydrogen, hydroxyl or be selected from following group: alkyl, alkoxyl group, aryl,
Alkyl sulphonyl and aryl sulfonyl,
A
1Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl
Two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-,
R wherein
5Represent hydrogen, hydroxyl or be selected from following group: alkyl, aryl, alkoxyl group,
Alkyl sulphonyl and aryl sulfonyl,
A
2Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl
Two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A
3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl,
Formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen, or representative
Be selected from following group: alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl
Alkylsulfonyl, alkylamino, dialkyl amido, alkoxy carbonyl, the basic phosphorus of dialkoxy (sulphur)
Acyl group, alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy
Carbonyl, alkynyl, alkynyloxy group, alkynyl amino, alkynyloxy group carbonyl, cycloalkyl, cycloalkyl
Oxygen base, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy
Carbonyl, cycloalkyl alkoxy carbonyl, aryl, aryloxy, aralkyl, aralkoxy,
Aryloxycarbonyl, aromatic alkoxy carbonyl, heterocyclic radical, heterocyclic radical alkyl, heterocyclic radical alcoxyl
Base or heterocyclic radical alkoxy carbonyl, they each can choose wantonly and be substituted R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they each can choose wantonly be substituted and
Z representative is selected from following monocycle or double-ring is saturated or unsaturated group: heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they each can choose wantonly and be substituted,
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
The aromatic carbonyl compounds and the following acquisition of derivative thereof of the replacement of novel logical formula I: in the presence of the reaction auxiliary, make the aromatics nitrile of the replacement of logical formula II if suit
Wherein
R
1, R
2With Z each as defined above
With water, hydrogen sulfide or ammonia react, and the general formula of gained (aromatic carboxylic acid's or derivatives thereof of I replacement a)
Wherein Q, R
1, R
2With Z each as defined above
If suit, change into the aromatic carbonyl compounds or derivatives thereof of the replacement consistent by ordinary method with the above-mentioned definition of leading to the formula I compound.
The aromatic carbonyl compounds of the replacement of novel logical formula I has strong weeding activity.
In definition, saturated or aliphatic unsaturated hydrocarbon as alkyl, alkane two bases, alkenyl or alkynyl, also comprises and the heteroatoms combination, as the situation of alkoxyl group, alkylthio or alkylamino, is straight or branched under each situation.
Halogen is represented fluorine, chlorine, bromine or iodine usually, preferably represents fluorine, chlorine or bromine and special representative's fluorine or chlorine.
The present invention preferably provides the formula I compound, wherein
Q represents oxygen, sulphur or imino-(NH),
R
1Represent hydrogen, fluorine, chlorine or bromine,
R
2Represent following radicals
-A
1-A
2-A
3A wherein
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-, R wherein
4Represent hydrogen, hydroxyl or be selected from following group: C
1-C
4-alkyl, C
1-C
4-alkoxyl group, phenyl, C
1-C
4-alkyl sulphonyl and phenyl sulfonyl, A
1Also representative is selected from following group: C
1-C
6-alkane two bases, C
2-C
6-alkene two bases, C
2-C
6-alkynes two bases, C
3-C
6-cycloalkyl two bases, C
3-C
6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace A by fluorine or chlorine
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-, R wherein
5Represent hydrogen, hydroxyl or be selected from following group: C
1-C
4-alkyl, C
1-C
4-alkoxyl group, phenyl, C
1-C
4-alkyl sulphonyl and phenyl sulfonyl, A
2Also representative is selected from following group: C
1-C
6-alkane two bases, C
2-C
6-alkene two bases, C
2-C
6-alkynes two bases, C
3-C
6-cycloalkyl two bases, C
3-C
6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace A by fluorine or chlorine
3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl, formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen; or representative is selected from following group: the basic phosphoryl of alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylamino, dialkyl amido, alkoxy carbonyl and dialkoxy (sulphur), they each have 1 to 6 carbon atom and each can be chosen wantonly by halogen, C at moieties
1-C
4-alkoxyl group or C
1-C
4-Alkoximino replaces, A
3Also representative is selected from following group: alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy carbonyl, alkynyl, alkynyloxy group, alkynyl amino and alkynyloxy group carbonyl, they respectively have 2 to 6 carbon atoms in alkenyl, alkylidene group or alkynyl and each is optional by halogen replacement, A
3Also representative is selected from following group: cycloalkyl, cycloalkyl oxy, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy carbonyl and cycloalkyl alkoxy carbonyl, they each on alkyl group, have 1 to 4 carbon atom and each is optional by halogen, cyano group, carboxyl, C having 3 to 6 carbon atoms on the group of naphthene base and choose wantonly
1-C
4-alkyl and/or C
1-C
4-alkoxyl group-carbonyl substituted,
A
3Also represent each can choose wantonly by nitro, cyano group, carboxyl, halogen, C
1-C
4-alkyl, C
1-C
4-haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-halogenated alkoxy and/or C
1-C
4-alkoxyl group-carbonyl substituted be selected from following group: phenyl, phenoxy group, phenyl-C
1-C
4-alkyl, phenyl-C
1-C
4-alkoxyl group, phenyloxycarbonyl and phenyl-C
1-C
4-alkoxy carbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, pyrazolyl-C
1-C
4-alkyl, furyl-C
1-C
4-alkyl, thienyl-C
1-C
4-alkyl, oxazolyl-C
1-C
4-alkyl, isoxazolyl-C
1-C
4-alkyl, thiazolyl-C
1-C
4-alkyl, pyridyl-C
1-C
4-alkyl, pyrimidyl-C
1-C
4-alkyl, pyrazolyl methoxyl group, furyl methoxyl group are represented perhydro pyranyl methoxyl group or pyridyl methoxyl group, R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they respectively have 1 to 6 carbon atom on alkyl and each is optional by hydroxyl, cyano group, halogen, C
1-C
4-alkoxyl group or C
1-C
4It respectively is monocycle or the saturated or unsaturated group of two ring-types that-alkoxyl group-carbonyl substituted and Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 6 carbon atoms and 1 to 4 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional at the most three be selected from-CO-,-CS-,-SO-and/or SO
2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, halogen, C
1-C
6(it can choose wantonly by halogen or C again-alkyl
1-C
4The replacement of-alkoxyl group), C
2-C
6-alkenyl and C
2-C
6-alkynyl (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkoxyl group and C
1-C
6(they respectively can choose wantonly by halogen or C again-alkoxyl group-carbonyl
1-C
4The replacement of-alkoxyl group), C
2-C
6-alkenyloxy and C
2-C
6-alkynyloxy group (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkylthio, C
2-C
6-alkenyl thio and and C
2-C
6-alkynes sulfenyl (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkylamino and two-(C
1-C
4-alkyl) amino, C
3-C
6-cycloalkyl and and C
3-C
6-cycloalkyl-C
1-C
4(they respectively can choose wantonly by halogen and/or C again-alkyl
1-C
4The replacement of-alkyl), (they respectively can be chosen wantonly by nitro, cyano group, halogen, C again for phenyl, phenoxy group, thiophenyl, phenyl sulfinyl, phenyl sulfonyl and phenyl amino
1-C
4-alkyl, C
1-C
4-haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-halogenated alkoxy and/or C
1-C
4-alkoxyl group-carbonyl substituted),
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
The present invention provides the compound of logical formula I especially, wherein
Q represents oxygen, sulphur or imino-(NH),
R
1Represent hydrogen, fluorine or chlorine,
R
2Represent following radicals:
-A
1-A
2-A
3A wherein
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-, R wherein
4Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl and ethylsulfonyl, A
1Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases, A
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-, R wherein
5Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl, ethylsulfonyl, just-or sec.-propyl alkylsulfonyl and phenyl sulfonyl, A
2Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases, A
3Represent hydrogen; hydroxyl; amino; cyano group; nitro; carboxyl; formamyl; sulfo group; fluorine; chlorine; bromine; representative is selected from following group: methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; just-; different-; secondary-or tert-pentyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; just-; different-; secondary-or uncle's pentyloxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; just-or the sec.-propyl sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the sec.-propyl alkylsulfonyl; methylamino; ethylamino; just-or sec.-propyl amino; just-; different-; secondary-and tertiary butyl amino; dimethylamino; diethylamino; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; the dimethoxy phosphoryl; the diethoxy phosphoryl; dipropoxy phosphoryl and diisopropoxy phosphoryl; they each can choose wantonly by fluorine; chlorine; methoxyl group; oxyethyl group; methoxyimino or ethoxy imino replace, A
3Also representative is selected from following group: propenyl, butenyl, propenyloxy group, butenyloxy, propenyl amino, butenyl amino, propylidene amino, butylidene amino, propenyloxy group carbonyl, butenyloxy carbonyl, proyl, butynyl, third alkynyloxy group, fourth alkynyloxy group, proyl amino, butynyl amino, the third alkynyloxy group carbonyl and fourth alkynyloxy group carbonyl, they each can choose wantonly by fluorine or chlorine and replace A
3Also representative is selected from following group: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl oxygen base, cyclobutyl oxygen base, cyclopentyloxy, cyclohexyl oxygen base, the cyclopropyl methyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexyl methyl, cyclo propyl methoxy, cyclobutyl methoxy base, the cyclopentyl methoxyl group, the cyclohexyl methoxyl group, cyclopentylidene amino, cyclohexylidene amino, the cyclopentyloxy carbonyl, cyclohexyl oxygen base carbonyl, cyclopentyl methoxycarbonyl and cyclohexyl methoxycarbonyl, they each can choose wantonly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just-or sec.-propyl, methoxycarbonyl or ethoxy carbonyl replace, A
3Also representative is selected from following group: phenyl, phenoxy group, benzyl, styroyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl oxazolyl isoxazolyl, thiazolyl, isothiazolyl oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, the pyrazolyl methyl, furyl methyl, thienyl methyl oxazolyl methyl isoxazolyl methyl, the thiazolyl methyl, pyridylmethyl, Pyrimidylmethyl, the pyrazolyl methoxyl group, furyl methoxyl group and pyridyl methoxyl group, they each can choose wantonly by nitro, cyano group, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl, trifluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, difluoro-methoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxy carbonyl replace, R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or propoxy-, methylthio group, ethylmercapto group, just-or the iprotiazem base, methylamino, ethylamino, just-or sec.-propyl amino, they each can choose wantonly by hydroxyl, cyano group, fluorine, chlorine, methoxyl group, oxyethyl group, methoxycarbonyl or ethoxy carbonyl replace and the Z representative to be selected from following respectively be monocycle shape or the saturated and unsaturated group of two ring-types: in the heterocycle ring system, respectively have 2 to 5 carbon atoms and 1 to 3 nitrogen-atoms and also optionally contain aerobic or sulphur atom and/or optionally be selected from-CO-to too many by two,-CS-,-SO-and/or SO
2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, fluorine, chlorine, bromine; Methyl, ethyl, just-or sec.-propyl, just-, different-, secondary-or the tertiary butyl, (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyl, butenyl, proyl and butynyl (each can be chosen wantonly again by fluorine or chlorine and replace); Methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-and tert.-butoxy, methoxycarbonyl and ethoxy carbonyl (they each can choose wantonly again replace) by fluorine, chlorine, methoxyl group and oxyethyl group; Propenyloxy group, butenyloxy, third alkynyloxy group and fourth alkynyloxy group (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methylthio group, ethylmercapto group, just-or the iprotiazem base, just-, different-, secondary-or uncle's butylthio, propylene sulfenyl, butylene sulfenyl, propine sulfenyl and butine sulfenyl (they each can choose wantonly again replace) by fluorine or chlorine; Methylamino, ethylamino, just-or sec.-propyl amino, just-, different-, secondary-or tertiary butyl amino, dimethylamino and diethylamino; Cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; the cyclopropyl methyl; cyclobutylmethyl; (they respectively can be chosen wantonly again by fluorine for cyclopentyl-methyl and cyclohexyl methyl; chlorine; methyl; ethyl; just-or the sec.-propyl replacement); phenyl; phenoxy group; thiophenyl; the phenyl sulfinyl; (they respectively can be chosen wantonly again by nitro for phenyl sulfonyl and phenyl amino; cyano group; fluorine; chlorine; bromine; methyl; ethyl; just-or and propyl group; trifluoromethyl; methoxyl group; oxyethyl group; just-or different-propoxy-; difluoro-methoxy; trifluoromethoxy; methoxycarbonyl or ethoxy carbonyl replace)
Except prior art compound: 5-chloro-4-(1,3-dihydro 1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester and 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid methyl esters (known) and 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3 by DE-2102848, DE-2119260 and DE-2166456,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester (by " tetrahedron communication " [Tetrahedron Lett.] 34 (1993), 1889-1892 is known).
Q under each situation wherein
1Representative is selected from following group :-CO-,-CS-,-CH
2-,-CH (OH)-,-CHCl-,-CHBr-,-C (=CH
2)-,-C (=CHF)-,-C (=CF
2)-,-C (=CHCl)-,-C (=CHBr)-,-C (=CHOCHF
2)-,-C (=CHOCF
3)-,-C (=CHOCH
2CF
3)-, Q
2Represent oxygen, sulphur or be selected from following group :-CO-,-CS-,-CH
2-,-CHF-,-CF
2-,-CHCl-,-CHBr-,-CHOCHF
2-,-CHOCF
3-,-CHOCH
2CF
3-, R
6Represent hydrogen; amino; nitro; cyano group; carboxyl; formamyl; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; cyclopropyl; difluoromethyl; trifluoromethyl; one chlorodifluoramethyl-; methoxyl group; oxyethyl group; just-or isopropoxy; difluoro-methoxy; trifluoromethoxy; one chlorine difluoro-methoxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; the difluoro methylthio group; trifluoromethylthio; one chlorine difluoro methylthio group; methylamino; ethylamino; just-or sec.-propyl amino; dimethylamino; diethylamino; methoxycarbonyl or ethoxy carbonyl, and R
7Represent hydrogen, hydroxyl, amino, cyano group, methyl, ethyl, just-or sec.-propyl, difluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, or wherein, if suitable, two adjacent groups---R
6And R
6Or R
7And R
7Or R
6And R
8-representative respectively has alkane two bases or alkene two bases of four carbon atom at the most together, they each optional by fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl replace and choose wantonly in beginning (or at the end of) or in hydrocarbon chain, insert oxygen, sulphur or be selected from following group :-SO-, SO
2-,-N (CH
3)-and-N (C
2H
5)-.
Above-mentioned general or preferred group definition is suitable for the end product of formula I, and correspondingly is suitable for every kind and prepares starting raw material or the intermediate that needs under the situation.These group definition can make up on demand mutually, promptly comprise the combination between scope of providing of preferred compound.
Formula I examples for compounds grouping of the present invention is listed in hereinafter.Group 1
Q, R
1, R
2And R
3Respectively have the implication that provides in the form hereinafter:
Q | ????R 1 | ????R 2 | ????R 3 | ????Q | ????R 1 | ????R 2 | ????R 3 | |
O | ????H | ????F | ????OH | ????O | ????F | ????F | ????OH | |
O | ????F | ????Cl | ????OH | ????O | ????Cl | ????F | ????OH | |
O | ????Cl | ????Cl | ????OH | ????O | ????F | ????Br | ????OH | |
O | ????H | ????F | ????OCH 3 | ????O | ????F | ????F | ????OCH 3 | |
O | ????F | ????Cl | ????OCH 3 | ????O | ????Cl | ????F | ????OCH 3 | |
O | ????Cl | ????Cl | ????OCH 3 | ????O | ????F | ????Br | ????OCH 3 | |
O | ????H | ????F | ????SCH 3 | ????O | ????F | ????F | ????SCH 3 | |
O | ????F | ????Cl | ????SCH 3 | ????O | ????Cl | ????F | ????SCH 3 | |
O | ????Cl | ????Cl | ????SCH 3 | ????O | ????F | ????Br | ????SCH 3 | |
S | ????H | ????F | ????OH | ????S | ????F | ????F | ????OH | |
S | ????F | ????Cl | ????OH | ????S | ????Cl | ????F | ????OH | |
S | ????Cl | ????Cl | ????OH | ????S | ????F | ????Br | ????OH | |
S | ????H | ????F | ????OCH 3 | ????S | ????F | ????F | ????OCH 3 | |
S | ????F | ????Cl | ????OCH 3 | ????S | ????Cl | ????F | ????OCH 3 | |
S | ????Cl | ????Cl | ????OCH 3 | ????S | ????F | ????Br | ????OCH 3 | |
S | ????H | ????F | ????SCH 3 | ????S | ????F | ????F | ????SCH 3 | |
S | ????F | ????Cl | ????SCH 3 | ????S | ????Cl | ????F | ????SCH 3 |
?Q | ?R 1 | ?R 2 | ?R 3 | Q | ?R 1 | ?R 2 | R 3 | |
?S | ?Cl | ?Cl | ?SCH 3 | S | ?F | ?Br | SCH 3 | |
?NH | ?H | ?F | ?NH 2 | NH | ?F | ?F | NH 2 | |
?NH | ?F | ?Cl | ?NH 2 | NH | ?Cl | ?F | NH 2 | |
?NH | ?Cl | ?Cl | ?NH 2 | NH | ?F | ?Br | NH 2 | |
?NH | ?H | ?F | ?SCH 3 | NH | ?F | ?F | SCH 3 | |
?NH | ?F | ?Cl | ?SCH 3 | NH | ?Cl | ?F | SCH 3 | |
?NH | ?Cl | ?Cl | ?SCH 3 | NH | ?F | ?Br | SCH 3 | |
?O | ?H | ?COOH | ?OH | O | ?F | ?COOH | OH | |
?O | ?F | ?COOH | ?OH | O | ?Cl | ?COOH | OH | |
?O | ?Cl | ?COOH | ?OH | O | ?F | ?COOH | OH | |
?O | ?H | ?COOCH 3 | ?OCH 3 | O | ?F | ?COOCH 3 | OCH 3 | |
?O | ?F | ?COOCH 3 | ?OCH 3 | O | ?Cl | ?COOCH 3 | OCH 3 | |
?O | ?Cl | ?COOCH 3 | ?OCH 3 | O | ?F | ?COOCH 3 | OCH 3 | |
?O | ?H | ?OH | ?OH | O | ?F | ?SH | OH | |
?O | ?F | ?OH | ?OH | O | ?Cl | ?SH | OH | |
?O | ?Cl | ?OH | ?OH | O | ?F | ?NH 2 | OH | |
?O | ?H | ?OH | ?OCH 3 | O | ?F | ?SH | OCH 3 | |
?O | ?F | ?OH | ?OCH 3 | O | ?Cl | ?SH | OCH 3 | |
?NH | ?Cl | ?NH 2 | ?NH 2 | NH | ?F | ?NH 2 | NH 2 | |
?NH | ?H | ?OH | ?SCH 3 | NH | ?F | ?SH | SCH 3 | |
?NH | ?F | ?OH | ?SCH 3 | NH | ?Cl | ?SH | SCH 3 | |
?NH | ?Cl | ?OH | ?SCH 3 | NH | ?F | ?NH 2 | SCH 3 | |
?O | ?H | ?CH 3 | ?OCH 3 | O | ?F | ?OCH 3 | OCH 3 | |
?O | ?F | ?CH 3 | ?OCH 3 | O | ?Cl | ?OCH 3 | OCH 3 | |
?O | ?Cl | ?CH 3 | ?OCH 3 | O | ?F | ?SCH 3 | OCH 3 | |
?O | ?H | ?SCH 3 | ?OCH 3 | O | ?F | ?NHCH 3 | OCH 3 |
Group 2
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Group 3
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Group 6
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Group 14
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
Q, R
1, R
2And R
3Respectively have and for example organize the implication that provides in 1.
For example, use 2-(2-fluoro-4-cyano group-5-methoxyl group-phenyl)-4-methyl-5-difluoromethyl-2,4-dihydro-3H-1,2,4-triazole-3-ketone and water are as starting raw material, and the reaction path of the inventive method can illustrate with following reaction formula:
Formula II is provided at the General Definition of the aromatics nitrile that needs the replacement used as starting raw material in the inventive method of preparation formula I compound.In formula II, R
1, R
2Each preferably or particularly has those indicated R in the description of formula I compound of the present invention with Z
1, R
2Preferred or particularly preferred implication with Z.
The starting raw material formula II be known and/or can by the preparation of known method (referring to, EP-370332, EP-648749, DE-4238125, DE-4303376, US-5084084, WO95/29168).
The inventive method for preparing novel formula I compound is preferably carried out in the presence of the reaction auxiliary.These reaction auxiliarys comprise water and conventional organic thinner, oxygenant such as hydrogen peroxide or Textone, and thionamic acid.
When carrying out the inventive method, temperature of reaction can change in the scope of broad.Usually, reaction is at 0 ℃ to 150 ℃, preferably carries out under the temperature between 20 ℃ to 120 ℃.
Method of the present invention is normally carried out under normal pressure.Yet, the inventive method also can the pressurization or the decompression under---normally 0.1 the crust to 10 the crust between pressure under carry out.
When carrying out the inventive method, adopt the roughly starting raw material of equimolar amount usually.One of yet, also can excessive relative to the earth employing reactive component.Reaction carry out in the presence of the reaction auxiliary, and reaction mixture was stirred several hours under required temperature usually normally in the thinner that is fit to.Aftertreatment be with ordinary method carry out (referring to, the preparation embodiment).
Active compound of the present invention can be used as defoliating agent, siccative, kill the straw agent and in particular as weedicide.So-called weeds with regard to it the most in the broadest sense, are interpreted as being grown in all plants in the place that should not grow.Material of the present invention is as steriland herbicide or selective herbicide depends on used amount basically.
The compounds of this invention can relevant use with for example following plants: the broadleaf weed of following dependent of dead military hero: mustard belongs to, the grass of walking alone belongs to, Bedstraw, Stellaria, Matricaria, Anthemis, Achyranthes, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, japanese bearbind belongs to, sweet potato genus, Polygonum, Daubentonia, Ambrosia, Cirsium, bristlethistle, sonchus L, Solanum, the weldering Lepidium, Herba Clinopodii Polycephali belongs to, Vandellia, lamium, Veronica, abutilon, the thorn Rumex, Datura, Viola, the weasel hemp nettle belongs to, papaver, bachelor's-button, Trifolium, Ranunculus and Dandelion, the dicotyledonous crops of following dependent of dead military hero: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, linum, sweet potato genus, vetch, Nicotiana, tomato belongs to, Arachis, Btassica, Lactuca, Cucumis and Cucurbita, the monocotyledon weed of following dependent of dead military hero: Echinochloa, setaria, Panicum, knotgrass, ladder forage spp, annual bluegrass belongs to, festuca, yard grass belongs to, Brachiaria, lolium, Brome, Avena, Cyperus, jowar belongs to, Agropyron, Cynodon, Monochoria, genus fimbristylis, arrowhead belongs to, Eleocharis, the Fischer grass belongs to, Paspalum, ischaemum, the cusp Pittosporum, talon eria, Agrostis, amur foxtail belongs to and the wind grass belongs to the monocot crops of following dependent of dead military hero: Oryza, Zea, Triticum, Hordeum, Avena, Secale, jowar belongs to, Panicum, saccharum, Ananas, Asparagus and allium.
Yet the application of active compound of the present invention never is limited to these genus, and also can extend to other plant in an identical manner.
According to compound concentrations, the compound natural disposition controlling weeds that is suitable for going out, for example at industrial region and railway line, and the road and the square that have or do not have the plantation woods.Equally, compound can be used for preventing and treating the weeds of perennial crop, for example the weeds in forest, the decoration woods, orchard, vineyard, citrus woods, nut garden, any of several broadleaf plants plantation, cafetal, tea place, rubber plantation, oil palm plantation, cocoa plantation, mushy fruit woods and hops field, grassland, stadium and the pasture.And The compounds of this invention can also be used for optionally preventing and treating the weeds of annual crop.
Formula I compound of the present invention is particularly suitable for optionally preventing and treating unifacial leaf and broadleaf weed in unifacial leaf and the dicotyledonous crops in two kinds of modes before the bud and behind the bud.
Active compound can change into conventional preparation, as solution, emulsion, wettable powder, suspension agent, pulvis, the agent of dusting, paste, soluble powder, granule, suspension emulsion, with the natural or synthetic materials of active compound dipping, and wrap in micro-fine capsule in the polymkeric substance.
These preparations can be produced in a known manner, for example, with active compound with expand agent, i.e. liquid and/or mixes, and optional use tensio-active agent, i.e. emulsifying agent and/or dispersion agent and/or pore forming material with solid carrier.
Using water as under the situation that expands agent, also can make solubility promoter with organic solvent.The liquid solvent that is fit to mainly contains: aromatic substance, and as dimethylbenzene, toluene or alkylnaphthalene, chloro aromatic substance or chlorinated aliphatic hydrocarbon are as chlorinated benzene class, polyvinyl chloride-base or methylene dichloride, aliphatic hydrocrbon, as hexanaphthene or paraffin, for example petroleum cuts, mineral and vegetables oil, alcohols, as butanols or glycol with and ether and ester, ketone is as acetone, methylethylketone, methyl iso-butyl ketone (MIBK) or pimelinketone, intensive polar solvent, as dimethyl formamide or dimethyl sulfoxide (DMSO), and water.
The solid carrier that is fit to is: for example ammonium salt and ground natural mineral matter, as kaolin, clay, talcum, chalk, quartz, attapulgite, montmorillonite or diatomite, with ground synthetic mineral matter, as high dispersive silicon-dioxide, alumina and silicate, the solid carrier that is suitable for granule has: for example crush and fractionated natural mineral matter such as calcite, marble, float stone, sepiolite and rhombspar, and the synthetic particle of organic and inorganic powder and following organic particle: wood sawdust, coconut husk, corn cob and tobacco stem; The emulsifying agent and/or the pore forming material that are fit to are: for example nonionic and anionic emulsifier, as polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether, for example, the alkaryl polyglycol ether, alkylsulfonate, alkyl-sulphate, arylsulphonate and protein hydrolysate; The dispersion agent that is fit to is: for example, and lignin sulfite waste liquor and methylcellulose gum.
Can use the carboxymethyl cellulose and the natural and synthetic polymer of tackiness agent such as powdery, particle or latex form in the preparation, as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipid, as kephalin and Yelkin TTS, and synthetic phospholipid.Other tackiness agent can be mineral oil and vegetables oil.
Also can use tinting material, as mineral dye, for example ferric oxide, titanium oxide and Prussian blue, and organic dye are as the salt of alizarine dyestuff, azoic dyestuff and metal phthalocyanine dyestuff and micronutrient element such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Usually contain 0.1 to 95% active compound by weight in the preparation, preferred 0.5 to 90%.
Be controlling weeds, active compound of the present invention, its former state or with its dosage form also can be used as the mixture with known weedicide, whole preparation or the possible mixed thing of bucket and uses.
The possible common component of mixture is known weedicide, for example, acetochlor, acifluorfen (sodium salt), aclonifen, alachlor, alloxydim (sodium salt), ametryn, amidochlor, amidosulfuron, the spirit of sulphur grass, atrazine, azimsulfuron, benazolin, benfuresate, benzyl ethyl methyl (methyl esters), bentazone, benzofenap, benzoylpropethyl (ethyl ester), two alanyl phosphorus, bifenox, bromobutide, bromofenoxim, bromoxynil, Butachlor technical 92, the fourth grass is special, cafenstrole, block careless amine, chlomethoxyfen, weed eradication is flat, pyrazon, chlorimuron (ethyl ester), chlornitrofen, chlorsulfuron, chlorotoluron, cinmethylin, ether is yellow grand, clethodim, clodinafop (propargyl) clomazone, difluoro pyridine acid, clopyrasulfuron, cloransulam (methyl), cumyluron, cyanazine, the weed eradication spy, cyclosulfamuron, cycloxydim, cyhalofop (butyl), 2,4-drips, 2, the 4-Embutox, 2,4-drips propionic acid, desmedipham, di_allate, dicamba 98, diclofop-methyl (methyl esters), two benzene azoles are fast, diflufenican Ding Evil is grand, dimepiperate, dimethachlor, diformazan third second is clean, dimethenamid, the spirit of amino second fluorine, diphenamide, diquat, dithiopyr, Diuron Tech, daimuron, EPTC, esprocarb, ethalfluralin, Ethanetsulfuron (methyl esters), ethofumesate, ethoxyfen, etobenzanid oxazole diclofop-methyl ethyl ester, wheat straw volt (isopropyl ester), the wheat straw volt (isopropyl ester-L), wheat straw volt (methyl esters), the pyridine ethyl methyl, fluazifop (butyl ester), flumetsulam, flumiclorac (pentyl), flumioxazin, flumipropyn, fluometuron, the fluorine cisanilide, fluoroglycofenethyl (ethyl ester), amine grass azoles, flupropacil, the fluorenes butyric acid, the fluorine butanone, fluroxypyr, flurprimidol, flurtamone, Fomesafen, Glufosinate (ammonium salt), glyphosate (isopropyl ammonium salt), halosafen, pyrrole fluorine chlorine standing grain spirit (ethoxy ethyl ester), hexazinone, miaow grass ester (methyl esters), imazamethapyr, imazamox, the weed eradication cigarette, the weed eradication quinoline, Imazethapyr, imidazoles is yellow grand, ioxynil, isopropalin, isoproturon, isoxaben, isoxaflutole Evil grass ether, lactofen, lenacil, methoxydiuron, 2 first, 4 chlorine, Vi par, mefenacet, metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metsulfuron-methyl (methyl esters), the piperazine humulone, Hydram, monolinuron, naproanilide, napropamide, neburon, nicoculsfuron, norflurazon, orbencarb, oryzalin Evil humulone, oxyfluorfen, Paraquat, pendimethalin, phenmedipham, piperophos, the third careless amine, Fluoropyrimidinesulfuron (methyl esters), prometryn, propachlor, Stam F-34, propaquizafop, pentyne grass amine, prosulfocarb, prosulfuron, pyrazolate, pyrazosulfuron (ethyl ester), pyrazoxyfen, pyributicarb, pyridate, pyrithiobac (sodium), quinclorac, quinmerac, quizalofop (ethyl ester), quizalofop (tetrahydrochysene chaff ester), rimsulfuron, rare uncertain, simazine, simetryn, sulcitrione, sulfentrazone, ethyl methyl (methyl esters), grass sulphur phosphorus, tebutam, terbufos benzthiazuron, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr, thidiazimin, thiophene methyl (methyl esters), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl (methyl esters), TRICLOPYR ACID, tridiphane, trifluralin and fluorine amine yellow grand (triflusulfuron).
It also can be mixture with other known activity compound such as mycocide, sterilant, miticide, nematocides, bird repellent, plant food and soil conditioner.
Active compound can with itself, with its preparation or by further dilution and the type of service of preparation uses of warp, as direct available solution, suspension, emulsion, pulvis, paste and granule.They use with ordinary method, for example pour, spraying, atomizing or spread fertilizer over the fields or the like.
Active compound of the present invention can be used before plant sprout or behind the bud.They also can mix in the soil prior to seeding.
The amount of used active compound can change in quite wide scope.Consumption depends on required effect basically.Usually, usage quantity is between per hectare soil surface-area restrains to 10 kilograms with 1, and preferred per hectare 5 grams are to 5 kilograms.
The preparation of activeconstituents of the present invention and use can be referring to the following example.
Preparation embodiment:
Under about 45 ℃; 1-(4-cyano group-2-fluoro-5-formyl radical-phenyl)-3 with 1.0g (2.93mmol); 6-dihydro-2, the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 150ml water, 0.58g (6mmol) thionamic acid and 0.54g (6mmol) Textone stirred about 24 hours.With mixture and ethyl acetate jolting, isolate organic phase afterwards afterwards, with dried over sodium sulfate and filtration.Solvent evaporated from filtrate carefully under pump vacuum.
Provide the 1-(4,5-is two-carboxyl-2-fluoro-phenyl)-3 of 0.90g (theoretical value 82%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine is the amorphous residue.
Embodiment 2
1-(4 with 0.80g (2.24mmol), 5-pair-carboxyl-2-fluoro-phenyl)-3,6-dihydro-2, the methyl-sulfate of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 0.70g (5mmol) salt of wormwood, 0.64g (5mmol) and the mixture of 20ml acetone boil about 20 hours of heating down in backflow.Under pump vacuum mixture is concentrated afterwards, residue is used the 2N hcl acidifying with the digestion of 50ml water, reclaims with the 4ml ether afterwards, and under agitation slowly dilutes with sherwood oil.The crystalline product of gained separates by suction filtration.
Provide the 1-(4,5-bi-methoxy carbonyl-2-fluoro-phenyl)-3 of 0.38g (theoretical value 42%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 141 ℃ of fusing points.
Elder generation is with the 1-(3-oxyethyl group sulfuryl amino-2-fluoro-4-thiocarbamoyl-phenyl)-3 of 4.5g (1.0mmol); 6-dihydro-2; 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine is added in the 50ml methylene dichloride, drips 1.5g (1.2mmol) methyl-sulfate and mixes.About 3 hours of reaction mixture reflux, and (about 20 ℃) restir 15 hours at room temperature.After adding other 0.5ml methyl-sulfate, the mixture reheat refluxed 5 hours, concentrated under pump vacuum subsequently.Residue stirs with ether, and the crystalline product of gained is separated by suction filtration.
Provide 1-(3-ethylsulfonyl amino-2-fluoro-4-(S-methyl-sulfo-imido acyl group-phenyl)-3,6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 212 ℃ of the fusing points of 4.4g (theoretical value 94%) thus.
Be similar to preparation embodiment 1 to 3, and the general description of method produced according to the present invention, also make the formula I compound of for example listing in the table 1.
The formula II starting raw material
Under agitation; the pivalyl chloride of 0.17g (1.2mmol) is joined the 1-(4-cyano group-2-fluoro-5-trifluoroacetyl group amino-phenyl)-3 of 0.50g (1.2mmol); 6-dihydro-2; in the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 1ml triethylamine and 50ml acetonitrile; and reaction mixture stirred 18 hours down at 20 ℃, and 60 ℃ of following restir 15 hours.Afterwards mixture is concentrated under pump vacuum, residue is with 1N hydrochloric acid/ethyl acetate jolting, and isolates organic phase, with dried over sodium sulfate and filter.Filtrate concentrates under pump vacuum, and residue is by column chromatography aftertreatment (silica gel, chloroform/ethyl acetate, volume ratio 1: 1).
Except unreacted 1-(4-cyano group-2-fluoro-5-trifluoroacetyl group amino-phenyl)-3; 6-dihydro-2; 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine (first step part: 0.30g); also obtain the 1-(4-cyano group-2-fluoro-5-amino-phenyl)-3 of second stage part 0.2g (theoretical value 50%); 6-dihydro-2; 6-oxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, fusing point: 195 ℃.
The nitrite tert-butyl of 1.8g (21mmol) methyl acrylate, 1.6g (15.5mmol), the cupric chloride (II) of 1.6g (12mmol) and the mixture of 50ml acetonitrile are cooled to about 0 ℃, and under this temperature, drip the 1-(5-amino-4-cyano group-2-fluoro-phenyl)-3 of 3.3g (10mmol), 6-dihydro-2, the 20ml acetonitrile solution of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine.Allow this reaction mixture be warming up to room temperature, and under this temperature, stirred 18 hours.Behind the 1N hydrochloric acid that adds 20ml, with the mixture ethyl acetate extraction, the organic phase dried over sodium sulfate, and filter.Filtrate is concentrated, and residue is by the column chromatography aftertreatment.Provide 1-[4-cyano group-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl of 2.8g (theoretical value 65%) thus]-3,6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 46 ℃ of fusing points.
Stir down, to the 1-[4-cyano group that is cooled to 0 ℃ 2.0g (4.6mmol)-2-fluoro-5-(2-chloro-2-methoxycarbonyl-ethyl)-phenyl]-3,6-dihydro-3, the N of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine and 30ml, add 0.22g sodium hydride (concentration 60%) in the mixture of dinethylformamide, and reaction mixture stirred 15 minutes down at 0 ℃ earlier, under 20 ℃, stirring about 60 minutes afterwards, and stirring 6 hours down at 60 ℃ at last.Afterwards mixture is concentrated under pump vacuum, residue stirs with isopropyl ether, and the crystalline product of gained separates with suction filtration.
Provide 1-[4-cyano group-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl-3 of 1.1g (theoretical value 60%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 154 ℃ of fusing points.
Step 3
To the 1-[4-cyano group that is cooled to the 8.7g (22mmol) under-70 ℃-2-fluoro-5-(2-methoxycarbonyl-vinyl)-phenyl]-3,6-dihydro-2 continues in the mixture of 6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine and 600ml methylene dichloride to import ozone 45 minutes.Remove cooling bath afterwards, and mixture is mixed with the 10ml dimethyl sulfide.After mixture is warming up to greenhouse (about 20 ℃), phase-splitting, organic phase washes with water, with dried over sodium sulfate and filtration.Filtrate concentrates under pump vacuum, and residue digests with ether, isolates crystalline product by suction filtration.
Provide the 1-(4-cyano group-2-fluoro-5-formyl radical-phenyl)-3 of 7.4g (theoretical value 99%) thus, 6-dihydro-2,6-dioxo-3-methyl-4-Trifluoromethyl-1 (2H)-pyrimidine, 177 ℃ of fusing points.Application Example: test solvent before the embodiment A bud: 5 parts of weight acetone emulsifying agents: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
The seed of test plant is broadcast in the common soil.After about 24 hours, active agent preparations is sprayed on the soil with the required active compound amount of per unit area.Select the concentration of spraying fluid, active compound amount required under each situation is used with the amount of 1000 premium on currency/hectares.
After three weeks, the degree of damage of plant and the developmental phase of untreated control are compared, make infringement %.
Numerical value is meant:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, for example, under the amount of application of 60g/ha, for example prepare embodiment 2 compounds weeds are demonstrated very strong activity, belong to (100%) as wild avena sativa (80%), setaria (95%), abutilon (100%), Amaranthus (100%), Bedstraw (95%) and mustard.Test solvent behind the Embodiment B bud: 5 parts of weight acetone emulsifying agents: the alkaryl polyglycol ether of 1 part of weight
When preparing the active agent preparations that is fit to, with the active compound of 1 part of weight and the solvent of described amount, with the emulsifying agent adding of described amount, and water is diluted to desired concn with this missible oil.
The test plant that highly is 5-15cm is sprayed with the required active compound amount of per unit area with active agent preparations.Select the concentration of spraying fluid, active compound amount required under each situation is used with the amount of 1000 premium on currency/hectares.
After three weeks, the degree of damage of plant and the developmental phase of untreated control are compared, make infringement %.
Numerical value is meant:
0%=do not have effect (be untreated identical)
100%=damages fully
In this test, for example, under the amount of application of 60g/ha, for example prepare embodiment 2 compounds weeds are demonstrated very strong activity, belong to (100%) as abutilon (100%), Amaranthus (100%), Bedstraw (90%) and mustard.
Claims (8)
1. the aromatic carbonyl compounds and the derivative thereof that lead to formula I
Wherein Q represents oxygen, sulphur or imino-(NH), R
1Represent hydrogen or halogen, R
2Represent following radicals
-A
1-A
2-A
3
Wherein
A
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-, R wherein
4Represent hydrogen, hydroxyl or be selected from following group: alkyl, alkoxyl group, aryl, alkyl sulphonyl and aryl sulfonyl,
A
1Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-, R wherein
5Represent hydrogen, hydroxyl or be selected from following group: alkyl, aryl, alkoxyl group, alkyl sulphonyl and aryl sulfonyl,
A
2Also representative is selected from following group: alkane two bases, alkene two bases, alkynes two bases, cycloalkyl two bases, cycloalkenyl group two bases and aromatic hydrocarbons two bases, they each can choose wantonly and be substituted,
A
3Represent hydrogen; hydroxyl; amino; cyano group; isocyano-; thiocyano; nitro; carboxyl; formamyl; thiocarbamoyl; sulfo group; chlorosulfonyl; halogen; or representative is selected from following group: alkyl; alkoxyl group; alkylthio; alkyl sulphinyl; alkyl sulphonyl; alkylamino; dialkyl amido; alkoxy carbonyl; the basic phosphoryl of dialkoxy (sulphur); alkenyl; alkenyloxy; alkenyl amino; alkylidene amino; the alkenyloxy carbonyl; alkynyl; alkynyloxy group; alkynyl amino; the alkynyloxy group carbonyl; cycloalkyl; cycloalkyl oxy; cycloalkylalkyl; cycloalkyl alkoxy; cycloalkylidene amino; the cycloalkyl oxy carbonyl; cycloalkyl alkoxy carbonyl; aryl; aryloxy; aralkyl; aralkoxy; aryloxycarbonyl; aromatic alkoxy carbonyl; heterocyclic radical; the heterocyclic radical alkyl; heterocyclic radical alkoxyl group or heterocyclic radical alkoxy carbonyl; they each can choose wantonly and be substituted
R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they each can choose wantonly be substituted and
Z representative is selected from following monocycle or double-ring is saturated or unsaturated group: heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they each can choose wantonly and be substituted,
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
2. according to the aromatic carbonyl compounds of the logical formula I of claim 1, it is characterized in that,
Q represents oxygen, sulphur or imino-(NH),
R
1Represent hydrogen, fluorine, chlorine or bromine,
R
2Represent following radicals
-A
1-A
2-A
3
Wherein
A
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-, R wherein
4Represent hydrogen, hydroxyl or be selected from following group: C
1-C
4-alkyl, C
1-C
4-alkoxyl group, phenyl, C
1-C
4-alkyl sulphonyl and phenyl sulfonyl,
A
1Also representative is selected from following group: C
1-C
6-alkane two bases, C
2-C
6-alkene two bases, C
2-C
6-alkynes two bases, C
3-C
6-cycloalkyl two bases, C
3-C
6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace by fluorine or chlorine,
A
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-, R wherein
5Represent hydrogen, hydroxyl or be selected from following group: C
1-C
4-alkyl, C
1-C
4-alkoxyl group, phenyl, C
1-C
4-alkyl sulphonyl and phenyl sulfonyl,
A
2Also representative is selected from following group: C
1-C
6-alkane two bases, C
2-C
6-alkene two bases, C
2-C
6-alkynes two bases, C
3-C
6-cycloalkyl two bases, C
3-C
6-cycloalkenyl group two bases and phenylene, they each can choose wantonly and replace by fluorine or chlorine,
A
3Represent hydrogen, hydroxyl, amino, cyano group, isocyano-, thiocyano, nitro, carboxyl, formamyl, thiocarbamoyl, sulfo group, chlorosulfonyl, halogen; or representative is selected from following group: the basic phosphoryl of alkyl, alkoxyl group, alkylthio, alkyl sulphinyl, alkyl sulphonyl, alkylamino, dialkyl amido, alkoxy carbonyl and dialkoxy (sulphur), they each have 1 to 6 carbon atom and each can be chosen wantonly by halogen, C at moieties
1-C
4-alkoxyl group or C
1-C
4-Alkoximino replaces,
A
3Also representative is selected from following group: alkenyl, alkenyloxy, alkenyl amino, alkylidene amino, alkenyloxy carbonyl, alkynyl, alkynyloxy group, alkynyl amino and alkynyloxy group carbonyl, they each have on alkenyl, alkylidene group or alkynyl that 2 to 6 carbon atoms and each are optional to be replaced by halogen
A
3Also representative is selected from following group: cycloalkyl, cycloalkyl oxy, cycloalkylalkyl, cycloalkyl alkoxy, cycloalkylidene amino, cycloalkyl oxy carbonyl and cycloalkyl alkoxy carbonyl, they each on alkyl group, have 1 to 4 carbon atom and each is optional by halogen, cyano group, carboxyl, C having 3 to 6 carbon atoms on the group of naphthene base and choose wantonly
1-C
4-alkyl and/or C
1-C
4-alkoxyl group-carbonyl substituted,
A
3Also represent each can choose wantonly by nitro, cyano group, carboxyl, halogen, C
1-C
4-alkyl, C
1-C
4-haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-halogenated alkoxy and/or C
1-C
4-alkoxyl group-carbonyl substituted be selected from following group: phenyl, phenoxy group, phenyl-C
1-C
4-alkyl, phenyl-C
1-C
4-alkoxyl group, phenyloxycarbonyl and phenyl-C
1-C
4-alkoxy carbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, pyrazolyl-C
1-C
4-alkyl, furyl-C
1-C
4-alkyl, thienyl-C
1-C
4-alkyl, oxazolyl-C
1-C
4-alkyl, isoxazolyl-C
1-C
4-alkyl, thiazolyl-C
1-C
4-alkyl, pyridyl-C
1-C
4-alkyl, pyrimidyl-C
1-C
4-alkyl, pyrazolyl methoxyl group, furyl methoxyl group are represented perhydro pyranyl methoxyl group or pyridyl methoxyl group,
R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: alkyl, alkoxyl group, alkylthio and alkylamino, they respectively have 1 to 6 carbon atom on alkyl and each is optional by hydroxyl, cyano group, halogen, C
1-C
4-alkoxyl group or C
1-C
4-alkoxyl group-carbonyl substituted and
It respectively is monocycle or the saturated or unsaturated group of two ring-types that Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 6 carbon atoms and 1 to 4 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional at the most three be selected from-CO-,-CS-,-SO-and/or SO
2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they optional by-or a plurality ofly be selected from following group and replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, halogen, C
1-C
6(it can choose wantonly by halogen or C again-alkyl
1-C
4The replacement of-alkoxyl group), C
2-C
6-alkenyl and C
2-C
6-alkynyl (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkoxyl group and C
1-C
6(they respectively can choose wantonly by halogen or C again-alkoxyl group-carbonyl
1-C
4The replacement of-alkoxyl group), C
2-C
6-alkenyloxy and C
2-C
6-alkynyloxy group (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkylthio, C
2-C
6-alkenyl thio and and C
2-C
6-alkynes sulfenyl (they respectively can be chosen wantonly again by halogen and replace), C
1-C
6-alkylamino and two-(C
1-C
4-alkyl) amino, C
3-C
6-cycloalkyl and C
3-C
6-cycloalkyl-C
1-C
4(they respectively can choose wantonly by halogen and/or C again-alkyl
1-C
4The replacement of-alkyl), (they respectively can be chosen wantonly by nitro, cyano group, halogen, C again for phenyl, phenoxy group, thiophenyl, phenyl sulfinyl, phenyl sulfonyl and phenyl amino
1-C
4-alkyl, C
1-C
4-haloalkyl, C
1-C
4-alkoxyl group, C
1-C
4-halogenated alkoxy and/or C
1-C
4-alkoxyl group-carbonyl substituted),
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
3. according to the aromatic carbonyl compounds of the logical formula I of claim 1, it is characterized in that,
Q represents oxygen, sulphur or imino-(NH),
R
1Represent hydrogen, fluorine or chlorine,
R
2Represent following radicals:
-A
1-A
2-A
3
Wherein
A
1Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
4-, R wherein
4Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl and ethylsulfonyl,
A
1Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases
A
2Represent singly-bound, represent oxygen, sulphur ,-SO-,-SO
2-,-CO-or group-N-R
5-, R wherein
5Represent hydrogen, hydroxyl or be selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methyl sulphonyl, ethylsulfonyl, just-or sec.-propyl alkylsulfonyl and phenyl sulfonyl,
A
2Also representative is selected from following group: methylene radical, second-1,1-two bases, second-1,2-two bases, the third-1,1-two bases, the third-1,2-two bases, the third-1,3-two bases, ethene-1,2-two bases, propylene-1,2-two bases, propylene-1,3-two bases, acetylene-1,2-two bases, propine-1,2-two base and propine-1,3-two bases
A
3Represent hydrogen; hydroxyl; amino; cyano group; nitro; carboxyl; formamyl; sulfo group; fluorine; chlorine; bromine; representative is selected from following group: methyl; ethyl; just-or sec.-propyl; just-; different-; secondary-or the tertiary butyl; just-; different-; secondary-or tert-pentyl; methoxyl group; oxyethyl group; just-or isopropoxy; just-; different-; secondary-or tert.-butoxy; just-; different-; secondary-or uncle's pentyloxy; methylthio group; ethylmercapto group; just-or the iprotiazem base; just-; different-; secondary-or uncle's butylthio; methylsulfinyl; the ethyl sulfinyl; just-or the sec.-propyl sulfinyl; methyl sulphonyl; ethylsulfonyl; just-or the sec.-propyl alkylsulfonyl; methylamino; ethylamino; just-or sec.-propyl amino; just-; different-; secondary-and tertiary butyl amino; dimethylamino; diethylamino; methoxycarbonyl; ethoxy carbonyl; just-or isopropoxy carbonyl; the dimethoxy phosphoryl; the diethoxy phosphoryl; dipropoxy phosphoryl and diisopropoxy phosphoryl; they each can choose wantonly by fluorine; chlorine; methoxyl group; oxyethyl group; methoxyimino or ethoxy imino replace
A
3Also representative is selected from following group: propenyl, butenyl, propenyloxy group, butenyloxy, propenyl amino, butenyl amino, propylidene amino, butylidene amino, propenyloxy group carbonyl, butenyloxy carbonyl, proyl, butynyl, third alkynyloxy group, fourth alkynyloxy group, proyl amino, butynyl amino, the third alkynyloxy group carbonyl and fourth alkynyloxy group carbonyl, they each can choose wantonly by fluorine or chlorine and replace
A
3Also representative is selected from following group: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl oxygen base, cyclobutyl oxygen base, cyclopentyloxy, cyclohexyl oxygen base, the cyclopropyl methyl, cyclobutylmethyl, cyclopentyl-methyl, cyclohexyl methyl, cyclo propyl methoxy, cyclobutyl methoxy base, the cyclopentyl methoxyl group, the cyclohexyl methoxyl group, cyclopentylidene amino, cyclohexylidene amino, the cyclopentyloxy carbonyl, cyclohexyl oxygen base carbonyl, cyclopentyl methoxycarbonyl and cyclohexyl methoxycarbonyl, they each can choose wantonly by fluorine, chlorine, cyano group, carboxyl, methyl, ethyl, just-or sec.-propyl, methoxycarbonyl or ethoxy carbonyl replace
A
3Also representative is selected from following group: phenyl, phenoxy group, benzyl, styroyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, (each optional all or part of hydrogenant) pyrryl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl oxazolyl isoxazolyl, thiazolyl, isothiazolyl oxadiazole base, thiadiazolyl group, pyridyl, pyrimidyl, triazinyl, the pyrazolyl methyl, furyl methyl, thienyl methyl oxazolyl methyl isoxazolyl methyl, the thiazolyl methyl, pyridylmethyl, Pyrimidylmethyl, the pyrazolyl methoxyl group, furyl methoxyl group and pyridyl methoxyl group, they each can choose wantonly by nitro, cyano group, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, just-or sec.-propyl, trifluoromethyl, methoxyl group, oxyethyl group, just-or isopropoxy, difluoro-methoxy, trifluoromethoxy, methoxycarbonyl and/or ethoxy carbonyl replace
R
3Represent hydrogen, hydroxyl, sulfydryl, amino (in the case, Q does not represent sulphur), or representative is selected from following group: methyl, ethyl, just-or sec.-propyl, methoxyl group, oxyethyl group, just-or isopropoxy, methylthio group, ethylmercapto group, just-or iprotiazem base, methylamino, ethylamino, just-or sec.-propyl amino, they each can choose wantonly by hydroxyl, cyano group, fluorine, chlorine, methoxyl group, oxyethyl group, methoxycarbonyl or ethoxy carbonyl replace and
It respectively is monocycle shape or the saturated and unsaturated group of two ring-types that Z representative is selected from following: in the heterocycle ring system, respectively have 2 to 5 carbon atoms and 1 to 3 nitrogen-atoms and also optional contain aerobic or sulphur atom and/or optional to too many by two be selected from-CO-,-CS-,-SO-and/or SO
2-group heterocyclic radical (except: piperazinyl), heterocyclic radical amino and heterocyclic radical imino-, they are optional to be selected from following group by one or more and to replace: nitro, hydroxyl, amino, cyano group, carboxyl, formamyl, thiocarbamoyl, fluorine, chlorine, bromine; Methyl, ethyl, just-or sec.-propyl, just-, different-, secondary-or the tertiary butyl, (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyl, butenyl, proyl and butynyl (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methoxyl group, oxyethyl group, just-or isopropoxy, just-, different-, secondary-and tert.-butoxy, methoxycarbonyl and ethoxy carbonyl (they each can choose wantonly again replace) by fluorine, chlorine, methoxy or ethoxy; Propenyloxy group, butenyloxy, third alkynyloxy group and fourth alkynyloxy group (they respectively can be chosen wantonly again by fluorine or chlorine and replace); Methylthio group, ethylmercapto group, just-or the iprotiazem base, just-, different-, secondary-or uncle's butylthio, propylene sulfenyl, butylene sulfenyl, propine sulfenyl and butine sulfenyl (they each can choose wantonly again replace) by fluorine or chlorine; Methylamino, ethylamino, just-or sec.-propyl amino, just-, different-, secondary-or tertiary butyl amino, dimethylamino and diethylamino; Cyclopropyl; cyclobutyl; cyclopentyl; cyclohexyl; the cyclopropyl methyl; cyclobutylmethyl; (they respectively can be chosen wantonly again by fluorine for cyclopentyl-methyl and cyclohexyl methyl; chlorine; methyl; ethyl; just-or the sec.-propyl replacement); phenyl; phenoxy group; thiophenyl; the phenyl sulfinyl; (they respectively can be chosen wantonly again by nitro for phenyl sulfonyl and phenyl amino; cyano group; fluorine; chlorine; bromine; methyl; ethyl; just-or sec.-propyl; trifluoromethyl; methoxyl group; oxyethyl group; just-or different-propoxy-; difluoro-methoxy; trifluoromethoxy; methoxycarbonyl or ethoxy carbonyl replace)
Except prior art compound: 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-O-Anisic Acid ethyl ester, 5-chloro-4-(1,3-dihydro-1,3-dioxo-2H-isoindole-2-yl)-and O-Anisic Acid methyl esters, 8-chloro-3-(2-chloro-5-methoxyl group-4-methoxycarbonyl-phenyl)-3,4-dihydro-5-methoxyl group-quinazoline-6-carboxylate methyl ester.
4. the method for the aromatic carbonyl compounds of formula I is led in preparation,
R wherein
1, R
2, R
3, Q and Z each as defined in claim 1, described method is characterised in that, makes the aromatics nitrile of logical formula II
R wherein
1, R
2With Z each as defined in claim 1
With water, hydrogen sulfide or ammonia react, and the general formula of gained (aromatic carboxylic acid's or derivatives thereof of I replacement a)
Wherein
Q, R
1, R
2With define in each claim 1 of Z
Change into the aromatic carbonyl compounds or derivatives thereof of the replacement consistent with the above-mentioned definition of formula I compound by ordinary method.
5. herbicidal composition is characterized in that, they contain the aromatic carbonyl compounds of the formula I of at least a claim 1.
6. prevent and treat the method for undesired plant, it is characterized in that, the formula I compound effects that makes claim 1 is in undesired plant and/or its dried rhizome of rehmannia of dwelling.
7. the formula I compound of claim 1 is prevented and treated the application of undesired plant.
8. prepare the method for herbicidal composition, it is characterized in that, with the formula I aromatic carbonyl compounds of claim 1 with expand agent and/or tensio-active agent and mix.
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CN 97196302 CN1225086A (en) | 1996-07-11 | 1997-07-01 | Substituted aromatic carbonyl compounds and their derivatives |
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DE19627901.1 | 1996-07-11 | ||
CN 97196302 CN1225086A (en) | 1996-07-11 | 1997-07-01 | Substituted aromatic carbonyl compounds and their derivatives |
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1997
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