CN1156991A - 取代嘧啶(硫)酮 - Google Patents
取代嘧啶(硫)酮 Download PDFInfo
- Publication number
- CN1156991A CN1156991A CN95194892.XA CN95194892A CN1156991A CN 1156991 A CN1156991 A CN 1156991A CN 95194892 A CN95194892 A CN 95194892A CN 1156991 A CN1156991 A CN 1156991A
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- CN
- China
- Prior art keywords
- group
- alkyl
- base
- carbonyl
- necessity
- Prior art date
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- Granted
Links
- 150000003230 pyrimidines Chemical class 0.000 title claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- -1 thiocarbamoyl Chemical group 0.000 claims description 150
- 239000000460 chlorine Substances 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 35
- 229910052731 fluorine Inorganic materials 0.000 claims description 35
- 239000011737 fluorine Substances 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 33
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 33
- 239000005864 Sulphur Substances 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 18
- 125000001118 alkylidene group Chemical group 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000004450 alkenylene group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000000000 cycloalkoxy 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001345 alkine derivatives Chemical class 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 6
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 5
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- 125000001544 thienyl group Chemical group 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
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
- 150000001924 cycloalkanes Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000002363 herbicidal effect Effects 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- ZLWQUAWACCJNOG-UHFFFAOYSA-N CCC=CC(CC=NN)(C=CC)N Chemical compound CCC=CC(CC=NN)(C=CC)N ZLWQUAWACCJNOG-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- JNAHSTZIPLLKBQ-UHFFFAOYSA-N [O].CC=C Chemical compound [O].CC=C JNAHSTZIPLLKBQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- YAVVGPBYBUYPSR-UHFFFAOYSA-N benzene;oxygen Chemical compound [O].C1=CC=CC=C1 YAVVGPBYBUYPSR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 claims description 2
- 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 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[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
- 125000004368 propenyl group Chemical group C(=CC)* 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
- 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 150000001721 carbon Chemical group 0.000 claims 5
- MREIFUWKYMNYTK-UHFFFAOYSA-N 1H-pyrrole Chemical class C=1C=CNC=1.C=1C=CNC=1 MREIFUWKYMNYTK-UHFFFAOYSA-N 0.000 claims 1
- RABBMOYULJIAFU-UHFFFAOYSA-N 1h-pyrrole;thiophene Chemical class C=1C=CNC=1.C=1C=CSC=1 RABBMOYULJIAFU-UHFFFAOYSA-N 0.000 claims 1
- LAIQKCIHZIGVGJ-UHFFFAOYSA-N [S].C1=CN=CN=C1 Chemical compound [S].C1=CN=CN=C1 LAIQKCIHZIGVGJ-UHFFFAOYSA-N 0.000 claims 1
- 239000006096 absorbing agent Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 5
- 239000002585 base Substances 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 150000004702 methyl esters Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 3
- LVOYSBZJJWPUBD-UHFFFAOYSA-N 6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound OC1=CC(C(F)(F)F)=NC=N1 LVOYSBZJJWPUBD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000209510 Liliopsida Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 3
- 239000012876 carrier material Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 235000015320 potassium carbonate Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 2
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 2
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- 241000219144 Abutilon Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 241000427159 Achyranthes Species 0.000 description 2
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 2
- 241000219318 Amaranthus Species 0.000 description 2
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- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- KQSBZNJFKWOQQK-UHFFFAOYSA-N hystazarin Natural products O=C1C2=CC=CC=C2C(=O)C2=C1C=C(O)C(O)=C2 KQSBZNJFKWOQQK-UHFFFAOYSA-N 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-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
- 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
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 150000002696 manganese Chemical class 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 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
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- WXUNXXKSYBUHMK-UHFFFAOYSA-N methyl 4-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate;methyl 5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl-1h-imidazol-2-yl)benzoate Chemical compound COC(=O)C1=CC=C(C)C=C1C1=NC(C)(C(C)C)C(=O)N1.COC(=O)C1=CC(C)=CC=C1C1=NC(C)(C(C)C)C(=O)N1 WXUNXXKSYBUHMK-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- XRKQMIFKHDXFNQ-UHFFFAOYSA-N n-cyclohexyl-n-ethylcyclohexanamine Chemical compound C1CCCCC1N(CC)C1CCCCC1 XRKQMIFKHDXFNQ-UHFFFAOYSA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
- XITQUSLLOSKDTB-UHFFFAOYSA-N nitrofen Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(Cl)C=C1Cl XITQUSLLOSKDTB-UHFFFAOYSA-N 0.000 description 1
- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 0.000 description 1
- 239000012074 organic phase 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
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-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
- 239000008188 pellet Substances 0.000 description 1
- 239000000575 pesticide Substances 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
- 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
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- FJSMZHRHSKLZBN-UHFFFAOYSA-N piperazine;toluene Chemical compound C1CNCCN1.CC1=CC=CC=C1 FJSMZHRHSKLZBN-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-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
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 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
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-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
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003516 soil conditioner Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920002994 synthetic fiber 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
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-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
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
- C07D239/40—One sulfur atom as doubly bound sulfur atom or as unsubstituted mercapto radical
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及通式(I)所示、其中Q、R1、R2、R3、R4及R5的含义为说明书中所述者的新取代嘧啶(硫)酮及其制备方法与其作除草剂的应用。
Description
本发明涉及新的取代嘧啶(硫)酮,涉及其制备方法及其作除草剂的应用。
虽然取代嘧啶已作为有潜在应用价值的除草剂成为一项专利申请的主体,但迄今为止仍无值得一提的实际意义(参见EP-A 568041)。
-A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-,
其中A4为氢、羟基、氨基、烷基、烷氧基、芳基、
烷基羰基、烷氧基羰基、烷基磺酰基、芳基羰基或芳
基磺酰基,或者
A1 还各为必要时取代的亚烷基、亚烯基、氮杂亚烯基、
亚炔基、环亚烷基、环亚烯基或亚芳基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基
团,其中A4为氢、烷基、芳基、烷基羰基、烷基磺
酰
基、或芳基磺酰基,
A2 还各为必要时取代的亚烷基、亚烯基、氮杂亚烯基、
亚炔基、环亚烷基、环亚烯基或亚芳基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、
氯磺酰基、卤素,或者必要时各为取代的烷基、烷氧
基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、
二烷基氨基、烷氧基羰基、二烷氧基(硫代)磷酰基、
链烯基、链烯氧基、链烯氨基、亚烷基氨基、链烯氧
基羰基、链炔基、链炔氧基、链炔氨基、链炔氧基羰
基、环烷基、环烷氧基、环烷基烷基、环烷基烷氧基、
环亚烷基氨基、环烷氧基羰基、环烷基烷氧基羰基、
芳基、芳氧基、芳烷基、芳基烷氧基、芳氧基羰基、
芳基烷氧基羰基、杂环基、杂环基烷基、杂环基烷氧
基或者杂环基烷氧基羰基,R4 为氢、卤素、烷基或卤代烷基,以及R5 为烷基或卤代烷基,或者同R4一起代表亚烷基。
通式(I)所示的新一类取代嘧啶(硫)酮的制备方法为:使通式(II)所示、其中R1、R2和R3诸含义同上所述且X为卤素的卤代芳烃与通式(III)所示、其中Q、R4、R5具上述含义的嘧啶(硫)酮反应,必要时在酸受体存在下,以及必要时在稀释剂存在下进行反应,并且必要时对如此制得的通式(I)所示化合物的Q、R1、R2、R3、R4和R5在上述基团定义范围内,用常规方法进一步进行化学修饰。
通式(I)所示的新一类取代嘧啶(硫)酮的特征是除草活性力强及选择性好。
在上述定义中,饱和或不饱和烃链如烷基、亚烷基、链烯基或链炔基-还有与杂原子相结合的如烷氧基、烷硫基或烷基氨基-各种情况下为直链或支链。
卤素一般指氟、氯、溴、碘,优选为氟、氯或溴,尤其优选为氟或氯。
本发明优先涉及通式(I)的化合物、式中:Q 为氧或硫,R1 为氢、氰基、硝基、氟、氯、溴,或者必要时由氟及/或氯取
代、具1至4个碳原子的烷基,R2 为氰基或硫代氨基甲酰基,R3 为下列基团
-A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、氨基、C1-C4-烷基、C1-C4-
烷氧基、苯基、C1-C4-烷基羰基、C1-C4-烷氧基羰
基、C1-C4-烷基磺酰基、苯基羰基或苯基磺酰基,或
者
A1 还各为必要时由氟、氯或溴取代的C1-C6-亚烷基、
C2-C6-亚烯基、C2-C6-氮杂亚烯基、C2-C6-亚炔基、
C3-C6-环亚烷基、C3-C6-环亚烯基或亚苯基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、C1-4烷基、C1-4烷
氧基、苯基、C1-4烷磺酰基或苯磺酰基,
A2 还各为必要时取代由氟、氯或溴取代的C1-C6-亚烷
基、C2-C6-亚烯基、C2-C6-氮杂亚烯基、C2-C6-亚炔
基、C3-C6-环亚烷基、C3-C6-环亚烯基或亚苯基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、
氯磺酰基、卤素,或者必要时各为由卤素或C1-C4-
烷氧基取代、烷基中含1至6个碳原子的烷基、烷氧
基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、
二烷基氨基、烷氧基羰基或二烷氧基(硫代)磷酰基,
A3 还各为必要时由卤素取代、其中链烯基、亚烷基或链
炔基具有2至6个碳原子的链烯基、链烯氧基、链烯
氨基、亚烷基氨基、链烯氧基羰基、链炔基、链炔氧
基、链炔氨基或链炔氧基羰基,
A3 还各为必要时由卤素、氰基、羧基、C1-C4-烷基及/
或C1-C4-烷氧基-羰基取代、其中环烷基具有3至6
个碳原子及必要时烷基中具有1至4个碳原子的环烷
基、环烷氧基、环烷基烷基、环烷基烷氧基、环亚
烷基氨基、环烷氧基羰基或环烷基烷氧基羰基,
A3 还各为必要时由硝基、氰基、羧基、卤素、C1-C4-
烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代
烷氧基及/或C1-C4-烷氧基-羰基取代的苯基、苯氧
基、苯基-C1-C4-烷基、苯基-C1-C4-烷氧基、苯氧基羰
基或苯基-C1-C4-烷氧基羰基,(各在必要时完全或部
分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃
基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、
噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡
唑基-C1-C4-烷基、呋喃基-C1-C4-烷基、噻吩基-C1-C4-
烷基、噁唑基-C1-C4-烷基、异噁唑基-C1-C4-烷基、噻
唑基-C1-C4-烷基、吡啶基-C1-C4-烷基、嘧啶基-C1-C4-
烷基、吡唑基甲氧基、呋喃基甲氧基,还为全氢化吡
喃基甲氧基或吡啶基甲氧基,R4 为氢、氟、氯或溴,或者为必要时由氟及/或氯取代、具有1
至4个碳原子的烷基,以及R5 为必要时由氟及/或氯取代、具有1至4个碳原子的烷基,或
者同R4一起代表C3-C4-亚烷基。
本发明尤其涉及通式(I)的化合物、其中各取代基的含义如下:R1 为氢、氟或氯,R2 为氰基或硫代氨基甲酰基,R3 为下列基团
-A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、甲基、乙基、正丙基或
异丙基、甲氧基、乙氧基、正-或异-丙氧基、甲基磺
酰基或乙酰磺酰基,或者
A1 还为亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙
基、1,2-亚丙基、1,3-亚丙基、1,2-亚乙烯基、1,2-
亚丙烯基、1,3-亚丙烯基、1,2-亚乙炔基、1,2-亚丙
炔基或1,3-亚丙炔基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、甲基、乙基、n-或i-丙
基、甲氧基、乙氧基、正-或异-丙氧基、甲基磺酰基、
乙基磺酰基、正-或异-丙基磺酰基或苯基磺酰基,
A2 还为亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙
基、1,2-亚丙基、1,3-亚丙基、1,2-亚乙烯基、1,2-
亚丙烯基、1,3-亚丙烯基、1,2-亚乙炔基、1,2-亚丙
炔基或1,3-亚丙炔基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,必要
时各为由氟、氯、甲氧基或乙氧基取代的甲基、乙基、
正-或异-丙基、正-,异-,仲-,或叔丁基、正-,异-,仲
-,或叔戊基、甲氧基、乙氧基、正-或异-丙氧基、正
-,异-,仲-,或叔丁氧基、正-,异-,仲-,或叔戊氧
基、甲硫基、乙硫基、正-或异-丙硫基、正-,异-,仲
-,或叔丁硫基、甲基磺酰基、乙基磺酰基、正-或异-
丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-或异-
丙基磺酰基、甲基氨基、乙基氨基、正-或异-丙基氨
基、正-,异-,仲-,或叔丁基氨基、二甲基氨基、二
乙基氨基、甲氧基羰基、乙氧基羰基、正-或异-丙氧
基羰基、二甲氧基磷酰基、二乙氧基磷酰基、二丙氧
基磷酰基或二异丙氧基磷酰基,
A3 还各为必要时由氟或氯取代丙烯基、丁烯基、丙烯氧
基、丁烯氧基、丙烯基氨基、丁烯基氨基、亚丙基氨
基、亚丁基氨基、丙烯氧基羰基、丁烯氧基羰基、丙
炔基、丁炔基、丙炔氧基、丁炔氧基、丙炔氨基、丁
炔氨基、丙炔氧基羰基或丁炔氧基羰基,
A3 还各为必要时由氟、氯、氰基、羧基、甲基、乙基、
正-或异-丙基、甲氧基羰基或乙氧基羰基取代的环丙
基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、
环戊氧基、环己氧基、环丙基甲基、环丁基甲基、环
戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧
基、环戊基甲氧基、环己基甲氧基、环亚戊基氨基、
环亚己基氨基、环戊氧基羰基、环己氧基羰基、环戊
基甲氧基羰基或环己基甲氧基羰基,
A3 还各为必要时由硝基、氰基、羧基、氟、氯、溴、甲
基、乙基、正-或异-丙基、三氟甲基、甲氧基、乙氧
基、正-或异-丙氧基、二氟甲氧基、三氟甲氧基、甲
氧基羰基及/或乙氧基羰基取代的苯基、苯氧基、苄
基、苯乙基、苄氧基、苯氧基羰基、苄氧基羰基、(各
在必要时完全或部分氢化的)吡咯基、吡唑基、咪唑
基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、
噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、
嘧啶基、三嗪基、吡唑甲基、呋喃甲基、噻吩甲基、
噁唑基甲基、异噁唑基甲基噻唑甲基、吡啶基甲基、
嘧啶基甲基、吡唑基甲氧基、呋喃基甲氧基、呋喃基
甲氧基或吡啶基甲氧基,R4 为氢、氟、氯、溴,或者为必要时由氟及/或氯取代的甲基或
乙基,以及R5 为必要时由氟及/或氯取代甲基或乙基。
上述一般的或优选范围内的基团定义既适用于通式(I)所示终产物,又相应方式适用于制备终产物所需的原料或者中间体。这些基团定义可以随意地互相组合,在所述优选化合物范围内也可任意组合。
按本发明方法制备通式(I)所示化合物时用作原料的卤代芳烃,由通式(II)给出一般定义。通式(II)中,R1、R2和R3的优选或特别优选的定义是已在上面通式(I)所示化合物的优选或特别优选R1、R2和R3所述的定义;X优选为氟、氯或溴,尤其为氟或氯。
通式(II)所示的原料是已知的及/或是可按已知方法制备的物质(参见EP-A431373,EP-A441004,EP-A597360)。
按本发明方法制备通式(I)所示化合物时还用作原料的嘧啶(硫)酮由通式(III)给出一般性定义。通式(III)中,Q、R4和R5优选或特别优选的定义同已就通式(I)所示化合物作为优选或特别优选的Q、R4和R5。
通式(III)所示的原料是已知的及/或是可按已知方法制备的物质(参见EP-A357201,EP-A395977,制备实施例)。
本发明方法的反应优选在一种相宜的酸受体存在下进行。这样的酸受体可用常用的无机或有机碱。举例来说,属于这种碱的有碱金属或碱土金属的氢化物、氢氧化物、氨化物、醇盐、乙酸盐、碳酸盐或酸式碳酸盐,例如氢化锂、氢化钠、氢化钾或氢化钙,氨基锂、氨基钠或氨基钾,甲醇钠或甲醇钾、乙醇钠或乙醇钾、丙醇钠或丙醇钾、异丙醇铝、叔丁醇钠或叔丁醇钾,氢氧化钠或氢氧化钾、氢氧化铵,乙酸钠、乙酸钾或乙酸钙、乙酸铵,碳酸钠、碳酸钾或碳酸钙、碳酸铵,碳酸氢钠、或碳酸氢钾,以及碱性有机氮化合物如三甲胺、三乙胺、三丙胺、三丁胺、乙基-二异丙基胺、N,N-二甲基环己胺、二环己基胺、乙基-二环己基胺、N,N-二甲基苯胺、N,N-二甲基-苄胺、吡啶、2-甲基-吡啶、3-甲基-吡啶及4-甲基-吡啶、2,4-二甲基-吡啶、2,6-二甲基-吡啶、3,4-二甲基-吡啶及3,5-二甲基-吡啶、5-乙基-2-甲基-吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、二氮杂二环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一烯(DBU)。
进行本发明方法所述的反应所用的稀释剂可采用常规的有机溶剂。属于这类有机溶剂的尤其为任选卤代的脂肪族烃、脂环族烃或芳香烃,如汽油、苯、甲苯、混合二甲苯、氯苯、二氯代苯、石油醚、己烷、环己烷、二氯甲烷、氯仿、四氯化碳;醚类如乙醚、异丙醚、二噁烷、四氢呋喃或者乙二醇二甲醚或乙二醇二乙醚;酮类,如丙酮、丁酮或甲基异丁基酮;腈类,如乙腈、丙腈或苯甲腈;酰胺类,如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基苯甲酰胺、N-甲基-吡咯烷酮或六甲基磷酸酰胺;酯类,如乙酸甲酯或乙酸乙酯;砜类,如二甲基亚砜;醇类如甲醇、乙醇、正-或异-丙醇;乙二醇单甲醚、乙二醇单乙醚、二乙二醇单甲醚、二乙二醇单乙醚,及它们与水的混合物,或者纯水。
实施本发明方法时,反应温度可在相对宽的范围内变化。一般在介于-20℃和+150℃之间的温度下操作,优选在介于-10℃和+120℃之间的温度下操作,尤其优选在0℃和100℃之间的温度下操作。
本发明方法一般在常压下实施。但也可以在高压或低压下—一般在0.1巴和10巴之间—实施。
为实现本发明方法,各个场合都使用接近等摩尔量所需原料。然而,各个场合也可以较大过量地使用两种所周反应物中的任何一种反应物。此种反应一般在适宜的稀释剂中进行,而且将反应混合物在各所需温度下搅拌数小时。本发明方法中的后处理各按常规方法来进行(参见制备实施例)。
本发明的活性物质可用作脱叶剂、干燥剂、除莠剂,尤其可用作除草剂。广义来说,杂草系指所有在不需要它的地方生长的植物。本发明的化合物是否完全或选择性地起除草剂作用,这主要取决于用量。
举例来说,本发明的生物活性物质可对下列植物使用:
双子叶杂草:欧白芥属、独行菜属、猪殃殃属、繁纟娄属、母菊属、春黄菊属、牛膝菊属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、番薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、Rorippa、水松叶属、母草属、野芝麻属、婆婆纳属、苘麻属、Emex、曼陀罗属、堇菜、鼬瓣花属、罂粟属、矢车菊属、三叶草属、毛莨属、蒲公英属。
双子叶作物属:棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、番薯属、巢菜属、菸草属、Lycopersicon、花生属、莼菜属、莴苣属、黄瓜属、南瓜属。
单子叶杂草:稗属、狗毛草属、黍属、马唐属、梯牧草属、早熟禾属、羊茅属、蟋蟀草属、臂形草属、毒麦属、雀麦属、燕麦属、莎草属、高粱属、冰草属、狗牙根属、雨久花属、飘拂草属、慈姑属、荸荠属、biao草属(Scirpus)、雀稗属、Ischaemum、尖瓣花属、龙爪茅属、翦股颖属、看麦娘属、Apera。
单子叶作物:稻属、玉蜀黍属、小麦属、大麦属、燕麦属、黑麦属、高粱属、黍属、甘蔗属、凤梨属、天门冬属、葱属。
然而,本发明活性物质的应用决不限于这些属,而可以同样的方式扩大应用于其它植物。
这类化合物只要浓度适宜,便可适合在工业场所和轨道设施,以及在有和没有树木植被的道路与广场上用来完全防、杀杂草。同样,这些化合物也可以用来防杀多年生植物,例如用于防杀营造林、观赏树林、果园、葡萄园、柑橘种植园、坚果种植园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕榈种植园、可可种植园、浆果种植园和啤酒花种植园中的杂草,以及防杀观赏与运动草坪和牧场上的杂草,并可用来选择性地防杀一年生植物中的杂草。
通式(I)所示的本发明化合物尤其适用于选择性防杀单子叶作物和双子叶作物中的双子叶杂草,不论这类杂草处于芽前或芽后。
所述活性物质可制成各种常用剂型,例如溶液剂、乳化液、喷洒粉剂、悬浮剂、可湿性粉剂、粉剂、糊剂、可溶性粉剂、颗粒剂、悬浮乳剂液浓缩液、浸有活性物质的天然材料及合成材料,以及聚合物的微胶囊。
上述不同剂型均以已知的方法来制备,例如将活性物质与稀释剂(也即液态溶剂及/或固态载体物质)混合,必要时使用表面活性剂(也即乳化剂及/或分散剂及/或发泡剂)。
在用水作稀释剂时,举例来说,也可用有机溶剂作助溶剂。适用的液态溶剂主要有:芳烃类,如二甲苯、甲苯、或烷基萘,氯代芳烃类和氯代脂肪烃烃类,如氯苯、氯乙烯或二氯甲烷,脂肪烃,如环己烷或烷属烃,例如各石油馏分、矿物油及植物油,醇类,如丁醇或乙二醇,及其醚和脂,酮类,如丙酮、甲基·乙基酮、甲基.异丁基酮或环己酮,强极性溶剂如二甲基甲酰胺及二甲亚砜,以及水。
固态载体物质可采用:例如铵盐及天然岩石粉末如高岭土、矾土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,以及人造石粉末如高分散性硅酸、氧化铝及硅酸盐,粒剂的固态载体物质可采用:例如粉碎并分级的天然岩石如方解石、大理石、浮石、海泡石、白云石,以及用无机及有机粉末制成的人造颗粒和诸如锯屑、椰壳、玉米穗和烟草茎之类有机材料制成的颗粒;乳化剂及/或发泡剂可采用:例如非离子型和离子型乳化剂如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、以及蛋白水解产物;分散剂可采用:例如木质素-亚硫酸盐废液和甲基纤维素。
各剂型中可使用粘着剂如羧甲基纤维素、天然与合成的粉末状、颗粒状或胶乳状聚合物,例如阿拉伯胶、聚乙烯醇、聚乙酸乙烯酯,天然磷脂如脑磷脂与卵磷脂,以及合成磷脂。其它添加剂可为矿物油与植物油。
还可能使用着色剂如无机颜料,例如氧化铁、二氧化钛、普鲁士蓝,以及有机染料,如茜素染料、偶氮染料与金属酞菁染料,以及微量营养物质如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐与锌盐。
各剂型一般含介乎0.1%(重量)与95%(重量)之间的活性物质,优选介乎0.5%(重量)与90%(重量)之间。
在有现成剂型或桶混装置的情况下,本发明活性物质可以单独或以其剂型的形式与已知的除草剂一起混合,用于防杀杂草。
可混用的已知除草剂,例如有酰替苯胺类(Anilide)如吡氟草胺(Diflufenican)、敌稗(Propanil),芳基羧酸类(Arylcarbonsaeuren)如二氯皮考啉酸(Dichlorpicolinsaeure)、甲氧二氯苯酸(Dicamba)、毒草定(Picloram),芳氧基烷属酸(Aryloxyalkansaeuren)如2,4-滴(2,4D)、2,4-滴丁酸(2,4DB)、2,4-滴丙酸(2,4DP)、氟草烟(Fluroxypyr)、2甲4氯钠(MCPA)、2甲4氯丙酸(MCPP)、乙氯草定(Triclopyr),芳氧基-苯氧基-烷属酸酯类(Aryloxy-phenoxy-alkansaeureester)如禾草灵(甲酯)(Diclofop-methyl)、噁唑禾草灵(乙酯)(Fenoxaprop-ethyl)、吡氟禾草灵(丁酯)(Fluazifop-butyl)、吡氟氯禾灵(甲酯)(Haloxyfop-methyl)、Quizalofop-ethyl,吖嗪酮(Azinone)如氯哒酮、(chloridazon)Norflurazon(氟哒酮),氨基甲酸酯类(Carbamate)如氯苯胺灵(Chlorpropham)、甜草灵(Desmedipham)、甲二威灵(Phenmedipham)、苯胺灵(Propham),氯乙酰苯胺类(Chloracetanilide)如杂草锁(Alachlor)、乙基乙草安(Acetochlor)、丁草锁(Butachlor)、吡草胺(Metazachlor)、甲氧毒草安(Metolachlor)、丙草胺(Pretilachlor)、毒草安(Propachloe),二硝基苯胺类(Dinitroaniline)如磺胺乐灵(Oryzalin)、二甲戊乐灵(Pendimethalin)、氟乐灵(Trifluralin),二苯醚类(Diphenylether)如三氟羧草醚(Acifluorfen)、甲酯除草醚(Bifenox)、乙羧氟草醚(Fluoroglycofen)、氟磺胺草醚(Fomesafen)、Halosafen、乳氟禾草灵(Lactofen)、乙氧氟甲草醚(Oxyfluorfen),尿素类(Harnstoffe)如绿麦隆(Chlortoluron)、敌草隆(Diuron)、伏草隆(Fluometuron)、异丙隆(Isoproturon)、利谷隆(Linuron)、噻唑隆(Methabenzthiazuron),羟胺类(Hydroxylamine)如禾草灭(Alloxy-dim)、烯草酮(Clethodim)、噻草酮(Cycloxydim)、稀禾定(Sethoxy-dim)、肟草酮(Tralkoxydim),咪唑啉酮类(Imidazolinone)如咪草酯(Imazametha-benz)、灭草烟(Imazapyr)、灭草喹(Imazaquin),腈类(Nitrile)如溴草腈(Bromoxynil)敌草腈(Dichlobenil)、碘草腈(Ioxynil),羟乙酰胺类(Oxyacetamide)如苯噻草胺(Mefenacet),磺酰脲类(Sulfonylharnstoffe/sulfonylurea)如苄嘧黄隆(Bensulfuron)、氯嘧黄隆(甲酯)(Chlorimuron-ethyl)、绿黄隆(Chlorsulfuron)、醚黄隆(Cinosulfuron)、甲黄隆(Metsulfuron-methyl)、烟嘧黄隆(Nicosulfuron)、氟嘧黄隆(Primisulfuron)、吡嘧黄隆(乙酯)(Pyrazosulfuron-ethyl)、噻黄隆(甲酯)(Thifensulfuron-methyl)、Trisulfuron、苯黄隆(甲酯)(Tribenuron-methyl),硫代氨基甲酸酯类(Thiolcarbamate)如异丁草丹(Butylate)、环己丹(Cycloate)、二氯烯丹(Diallate)、丙草丹(EPTC)、禾草畏(Esprocarb)、环草丹(Molinate)、苄草丹(Prosulfocarb)、杀草丹(Thiobencarb)、三氯烯丹(Triallate),三嗪类(Triazine)如阿特拉津(Atrazin疑为Atrazine)、丙腈津(Cyanazin,Cyanazine)、西玛津(Simazin,Simazine)、西玛净(Simetryne)、特丁草净(Terbutryne)、特丁津(Terbutylazin,Terbutylazine),三嗪酮类(Triazinone)如环嗪酮(Hexa-zinon)、甲苯嗪(Metamitron)、赛克嗪(Metribuzin),其它类如氨三唑(Aminotriazol)、呋草黄(Benfuresate)、苯达松(Bentazone)、环庚草醚(Cinmethylin)、异噁草酮(Clomazone)、二氯吡啶酸(Clopyralid)、草吡唑(Difenzoquat)、氟硫草定(Dithiopyr)、甜菜呋(Ethofumesate)、氟咯草酮(Fluorochloridone)、草胺膦(Glufosinate)、草甘膦(Glyphosate)、Isoxaben、哒草特(Pyridate)、二氯喹啉酸(Quinchlorac)、喹草酸(Quinmerac)、草硫膦(Sulphosate)、灭草环(Tridiphane)。
也可与诸如杀菌剂、杀虫剂、杀螨剂、杀线虫剂、防啄剂、植物营养剂及土壤结构改良剂之类其它已知活性物质混合。
这类活性物质可以单独以其各种剂型的形式施用,或以由各剂型进而稀释所得的施药形式来施用,各施用形式的例子如即时可用的溶液剂、悬浮剂、乳化剂、粉剂、糊剂及颗粒剂。施药以常规方法进行,例如泼浇、喷雾、洒、撒。
本发明活性物质既可芽前施药,也可芽后施药。也可在播种前加到土壤中。
此种活性物质的用量可在较大范围内变化,主要取决于所需效果的类型。一般,用量介乎每公顷土地面积5g与5kg之间,优选介乎每公顷10g与2kg之间。
本发明活性物质的制备与应用,可用下列实施例描述。
制备实施例:
实施例1
20℃下,将一种由3.0g(18.3mMol)6-三氟甲基-嘧啶-4-酮、2.5g(183mMol)碳酸钾和50ml二甲基亚砜组成的混合物搅拌15小时。然后,加入2.9g(18.3mMol)2,4,5-三氟-苯甲腈,并于60℃下将所得混合物搅拌8小时。该混合物经减压浓缩后,将残留物用水搅和,并将结晶产生的产物过滤分离出来。
制得2.7g(理论值49%的)3-(4-氰基-2,5-二氟-苯基)-6-三氟甲基-嘧啶-4-酮,其熔点为95℃。
60℃下,将一种由4.3g(14.3mMol)3-(4-氰基-2,5-二氟-苯基)-6-三氟甲基-嘧啶-4-酮(参见实施例1)、1.6g(14.3mMol)甲磺酰胺、2.0g(143mMol)碳酸钾和50ml二甲亚砜组成的混合物搅拌6小时,然后予以减压浓缩。将残留物溶于水,并于酸化后同二氯甲烷一起摇振。有机相用硫酸钠干燥,并予过滤。浓缩滤液,并将以残留物形式得到的粗产物用柱色谱法提纯(硅胶,乙酸乙酯/氯仿,体积比:1∶1)。
制得100mg(理论值2%的)3-(4-氰基-5-乙基磺酰基氨基-2-氟苯基)-6-三氟甲基-嘧啶-4-酮,其熔点为170℃。
表1:通式(I)所示化合物的各实施例实施例 Q R1 R2 R3 R4 R5 熔点编号 (℃)3 O F CN NHSO2CH3 H CH34 O H CN NHSO2CH3 H CF35 O F CN NHSO2CH3 H CF36 O H CSNH2 NHSO2C2H5 H CF37 O F CSNH2 NHSO2C2H5 H CF38 S F CN NHSO2C2H5 H CF39 O F CN NHSO2C3H7 H CHF210 O F CN NHSO2C4H9 H CF2Cl11 O F CN NHSO2C2H5 H C2F512 O H CSNH2 NHSO2CH3 CH3 CF313 O F CN OCH3 H CF314 O F CSNH2 OC2H5 CH3 CF315 S H CN
H CF3实施例Q R1 R2 R3 R4 R5 熔点编号 (℃)16 O F CN NH2 H CF317 O F CN NH-CH2-COOEt H CF318 O F CN CHO H CF319 O H CN COOEt H CF320 O F CN CH=CH-COOEt H CF321 O F CN S-CH2-COOMe H CF322 O F CN S-CH3 H CF2Cl23 O F CN SO2NH2 H CF324 O F CN NO2 H CF325 O F CN OH H CF326 O F CN SH H CF327 O F CN -CH2-COOEt H CF328 O F CN
H CF3通式(III)所示的原料:
实施例(III-1)
在60℃下,将一种由30g(288mMol)乙酸甲脒、354g(192mMol)三氟乙酸乙酯、24.5g(230mMol)碳酸钠和250ml甲醇组成的混合物搅拌20小时,冷却后再添加56g浓盐酸,将该混合物的pH值调至3左右,并经过滤将结晶产生的产物分离出来。
制得22.8g(理论值的48%)6-三氟甲基-嘧啶-4-酮,其熔点为157℃。
实施例A
苗前试验
溶剂: 5份丙酮(按重量计)
乳化剂: 1份烷基芳基聚乙二醇醚(按重量计)
为制备符合目的的活性物质制剂起见,按重量计,将1份活性物质同上述量的溶剂混合,加入上述量的乳化剂,并用水将该浓液稀释到所需浓度。
将待试植物的种子播在普通土壤中,24h后将上述活性物质制剂浇于该土壤中。试验时,保持每单位面积上的水分适当恒定。制剂中活性物质的浓度无关紧要,关键在于每单位面积的活性物质用量。三周后,评定植物相对于未处理的对照组的百分受害程度。意即:
0% = 无作用(同未处理对照组)
100% = 完全灭杀在此试验中,以按制备实施例2制得的化合物为例,用量为15g/公顷时,栽培植物呈现极良好的耐受性,例如小麦和大豆不受影响(0%),而对杂草则呈现强力的作用,例如苘麻属(90%)、苋属(80%)、豚草属牛膝菊属(100%)、茄属(80%)以及堇菜属(80%)。
Claims (8)
1、通式(I)所示的取代嘧啶(硫)酮,式中,Q 为氧或硫,R1 为氢、氰基、硝基、卤素、烷基或卤代烷基,R2 为氰基或硫代氨基甲酰基,R3 为下列基团
-A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-,
其中A4为氢、羟基、氨基、烷基、烷氧基、芳基、
烷基羰基、烷氧基羰基、烷基磺酰基、芳基羰基或芳
基磺酰基,或者
A1 还各为必要时取代的亚烷基、亚烯基、氮杂亚烯基、
亚炔基、环亚烷基、环亚烯基或亚芳基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、烷基、芳基、烷基羰基、烷基
磺酰基、或芳基磺酰基,
A2 还各为必要时取代的亚烷基、亚烯基、氮杂亚烯基、
亚炔基、环亚烷基、环亚烯基或亚芳基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、
氯磺酰基、卤素,或者必要时各为取代的烷基、烷氧
基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、
二烷基氨基、烷氧基羰基、二烷氧基(硫代)磷酰基、
链烯基、
链烯氧基、链烯氨基、亚烷基氨基、链烯氧基羰基、
链炔基、链炔氧基、链炔氨基、链炔氧基羰基、环烷
基、环烷氧基、环烷基烷基、环烷基烷氧基、环亚烷
基氨基、环烷氧基羰基、环烷基烷氧基羰基、芳基、
芳氧基、芳烷基、芳基烷氧基、芳氧基羰基、芳基烷
氧基羰基、杂环基、杂环基烷基、杂环基烷氧基或者
杂环基烷氧基羰基,R4 为氢、卤素、烷基或卤代烷基,以及R5 为烷基或卤代烷基,或者同R4一起代表亚烷基。
2、权利要求1所述通式(I)所示的取代嘧啶(硫)酮,其特征在于,Q 为氧或硫,R1 为氢、氰基、硝基、氟、氯、溴,或者必要时由氟及/或氯取
代、具1至4个碳原子的烷基,R2 为氰基或硫代氨基甲酰基,R3 为下列基团
A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、氨基、C1-C4-烷基、C1-C4-
烷氧基、苯基、C1-C4-烷基羰基、C1-C4-烷氧基羰
基、C1-C4-烷基磺酰基、苯基羰基或苯基磺酰基,或
者
A1 还各为必要时氟、氯、溴取代的C1-C6-亚烷基、C2-
C6-亚烯基、C2-C6-氮杂亚烯基、C2-C6-亚炔基、
C3-C6-环亚烷基、C3-C6-环亚烯基或亚苯基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、C1-C4-烷基、C1
-C4-烷氧基、苯基、C1-C4-烷基磺酰基、或,
苯基磺酰基,
A2 还各为必要时取代由氟、氯或溴取代的C1-C6-亚烷
基、C2-C6-亚烯基、C2-C6-氮杂亚烯基、C2-C6-亚炔
基、C3-C6-环亚烷基、C3-C6-环亚烯基或亚苯基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、硫代氨基甲酰基、磺基、
氯磺酰基、卤素,或者必要时各为由卤素或C1-C4-
烷氧基取代、烷基中含1至6个碳原子的烷基、烷氧
基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、
二烷基氨基、烷氧基羰基或二烷氧基(硫代)磷酰基,
A3 还各为必要时由卤素取代、其中链烯基、亚烷基或链
炔基具有2至6个碳原子的链烯基、链烯氧基、链烯
氨基、亚烷基氨基、链烯氧基羰基、链炔基、链炔氧
基、链炔氨基或链炔氧基羰基,
A3 还各为必要时由卤素、氰基、羧基、C1-C4-烷基及/
或C1-C4-烷氧基-羰基取代、其中环烷基具有3至6
个碳原子及必要时烷基中具有1至4个碳原子的环烷
基、、环烷氧基、环烷基烷基、环烷基烷氧基、环亚
烷基氨基、环烷氧基羰基或环烷基烷氧基羰基,
A3 还各为必要时由硝基、氰基、羧基、卤素、C1-C4-
烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代
烷氧基及/或C1-C4-烷氧基-羰基取代的苯基、苯氧
基、苯基-C1-C4-烷基、苯基-C1-C4-烷氧基、苯氧基羰
基或苯基-C1-C4-烷氧基羰基,(各在必要时完全或部
分氢化的)吡咯基、吡唑基、咪唑基、三唑基、呋喃
基、噻吩基、噁唑基、异噁唑基、噻唑基、异噻唑基、
噁二唑基、噻二唑基、吡啶基、嘧啶基、三嗪基、吡
唑基-C1-C4-烷基、呋喃基-C1-C4-烷基、噻吩基-C1-C4-
烷基、噁唑基-C1-C4-烷基、异噁唑基-C1-C4-烷基、噻
唑基-C1-C4-烷基、吡啶基-C1-C4-烷基、嘧啶基-C1-C4-
烷基、吡唑基甲氧基、呋喃基甲氧基,还为全氢化吡
喃基甲氧基或吡啶基甲氧基,R4 为氢、氟、氯或溴,或者为必要时由氟及/或氯取代、具有1
至4个碳原子的烷基,以及R5 为必要时由氟及/或氯取代、具有1至4个碳原子的烷基,或
者同R4一起代表C3-C4-亚烷基。
3、 权利要求1所述通式(I)所示的取代嘧啶(硫)酮,其特征在于,R1 为氢、氟或氯,R2 为氰基或硫代氨基甲酰基,R3 为下列基团
-A1-A2-A3
其中,
A1 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、甲基、乙基、正丙基或
异丙基、甲氧基、乙氧基、正-或异-丙氧基、甲基磺
酰基或乙酰磺酰基,或者
A1 还为亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙
基、1,2-亚丙基、1,3-亚丙基、1,2-亚乙烯基、1,2-
亚丙烯基、1,3-亚丙烯基、1,2-亚乙炔基、1,2-亚丙
炔基或1,3-亚丙炔基,
A2 为一个单键、氧、硫、-SO-、-SO2-、-CO-或者-N-A4-
基团,其中A4为氢、羟基、甲基、乙基、正-或异-
丙基、甲氧基、乙氧基、正-或异-丙氧基、甲基磺酰
基、乙基磺酰基、正-或异-丙基磺酰基或苯基磺酰基,
A2 还为亚甲基、1,1-亚乙基、1,2-亚乙基、1,1-亚丙
基、1,2-亚丙基、1,3-亚丙基、1,2-亚乙烯基、1,2-
亚丙烯基、1,3-亚丙烯基、1,2-亚乙炔基、1,2-亚丙
炔基或1,3-亚丙炔基,
A3 为氢、羟基、巯基、氨基、氰基、异氰基、硫氰酸基、
硝基、羧基、氨基甲酰基、磺基、氟、氯、溴,必要
时各为由氟、氯、甲氧基或乙氧基取代的甲基、乙基、
正-或异-丙基、正-,异-,仲-,或叔丁基、正-,异-,仲
-,或叔戊基、甲氧基、乙氧基、正-或异-丙氧基、正
-,异-,仲-,或叔丁氧基、正-,异-,仲-,或叔戊氧
基、甲硫基、乙硫基、正-或异-丙硫基、正-,异-,仲
-,或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正-
或异-丙基亚磺酰基、甲基磺酰基、乙基磺酰基、正-
或异-丙基磺酰基、甲基氨基、乙基氨基、正-或异-
丙基氨基、正-,异-,仲-,或叔丁基氨基、二甲基氨
基、二乙基氨基、甲氧基羰基、乙氧基羰基、正-或
异-丙氧基羰基、二甲氧基磷酰基、二乙氧基磷酰基、
二丙氧基磷酰基或二异丙氧基磷酰基,
A3 还各为必要时由氟或氯取代丙烯基、丁烯基、丙烯氧
基、丁烯氧基、丙烯基氨基、丁烯基氨基、亚丙基氨
基、亚丁基氨基、丙烯氧基羰基、丁烯氧基羰基、丙
炔基、丁炔基、丙炔氧基、丁炔氧基、丙炔氨基、丁
炔氨基、丙炔氧基羰基或丁炔氧基羰基,
A3 还各为必要时由氟、氯、氰基、羧基、甲基、乙基、
正-或异-丙基、甲氧基羰基或乙氧基羰基取代的环丙
基、环丁基、环戊基、环己基、环丙氧基、环丁氧基、
环戊氧基、环己氧基、环丙基甲基、环丁基甲基、环
戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧
基、环戊基甲氧基、环己基甲氧基、环亚戊基氨基、
环亚己基氨基、环戊氧基羰基、环己氧基羰基、环戊
基甲氧基羰基或环己基甲氧基羰基,
A3 还各为必要时由硝基、氰基、羧基、氟、氯、溴、甲
基、乙基、正-或异-丙基,三氟甲基、甲氧基、乙氧
基、正-或异-丙氧基,二氟甲氧基、三氟甲氧基、甲
氧基羰基及/或乙氧基羰基取代的苯基、苯氧基、苄
基、苯乙基、苄氧基、苯氧基羰基、苄氧基羰基、(各
在必要时完全或部分氢化的)吡咯基、吡唑基、咪唑
基、三唑基、呋喃基、噻吩基、噁唑基、异噁唑基、
噻唑基、异噻唑基、噁二唑基、噻二唑基、吡啶基、
嘧啶基、三嗪基、吡唑甲基、呋喃甲基、噻吩甲基、
噁唑基甲基、异噁唑基甲基噻唑甲基、吡啶基甲基、
嘧啶基甲基、吡唑基甲氧基、呋喃基甲氧基、呋喃基
甲氧基或吡啶基甲氧基,R4 为氢、氟、氯、溴,或者为必要时由氟及/或氯的甲基或乙基,
以及R5 为必要时由氟及/或氯取代甲基或乙基。
5、灭杀杂生植物的方法,其特征在于,使权利要求1至4所述的通式(I)所示取代嘧啶(硫)酮对植物或者植物的生长地域起作用。
6、权利要求1至4所述的通式(I)所示取代嘧啶(硫)酮在灭杀杂生植物方面的应用。
7、除草剂的制备方法,其特征在于,将权利要求1至4所述的通式(I)所示取代嘧啶(硫)酮与稀释剂及/或表面活性剂一起混合。
8、除草组合物,其特征在于,其中含有至少一种权利要求1至4所述的通式(I)所示取代嘧啶(硫)酮。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4431218.0 | 1994-09-02 | ||
DE4431218A DE4431218A1 (de) | 1994-09-02 | 1994-09-02 | Substituierte Pyrimidin(thi)one |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1156991A true CN1156991A (zh) | 1997-08-13 |
CN1121392C CN1121392C (zh) | 2003-09-17 |
Family
ID=6527213
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN95194892A Expired - Fee Related CN1121392C (zh) | 1994-09-02 | 1995-08-21 | 取代嘧啶(硫)酮 |
Country Status (10)
Country | Link |
---|---|
US (1) | US5877121A (zh) |
EP (1) | EP0804424A1 (zh) |
JP (1) | JPH10505073A (zh) |
KR (1) | KR100389528B1 (zh) |
CN (1) | CN1121392C (zh) |
AU (1) | AU3347295A (zh) |
BR (1) | BR9508778A (zh) |
DE (1) | DE4431218A1 (zh) |
MX (1) | MX9701569A (zh) |
WO (1) | WO1996007647A1 (zh) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19901846A1 (de) * | 1999-01-19 | 2000-07-20 | Bayer Ag | Substituierte Arylheterocyclen |
WO2004089914A1 (de) * | 2003-04-08 | 2004-10-21 | Basf Aktiengesellschaft | Benzolsulfonamid-derivate als herbizide oder desikkante/defoliante verbindungen |
TW200510305A (en) * | 2003-07-25 | 2005-03-16 | Wyeth Corp | Process for the preparation of CPLA2 inhibitors |
US7803940B2 (en) | 2006-11-24 | 2010-09-28 | Takeda Pharmaceutical Company Limited | Heteromonocyclic compound or a salt thereof having strong antihypertensive action, insulin sensitizing activity and the like production thereof and use thereof for prophylaxis or treatment of cardiovascular diseases, metabolic diseases and/or central nervous system diseases |
AU2013292950C1 (en) | 2012-07-18 | 2016-01-21 | Sunshine Lake Pharma Co., Ltd. | Nitrogenous heterocyclic derivatives and their application in drugs |
BR112015031291A2 (pt) | 2013-06-20 | 2017-07-25 | Bayer Cropscience Ag | derivados de sulfureto de arila e derivados de arilalquil sulfóxido como acaricidas e inseticidas |
CN105722830B (zh) | 2013-06-20 | 2019-06-04 | 拜耳作物科学股份公司 | 作为杀螨剂和杀昆虫剂的芳基硫醚衍生物和芳基亚砜衍生物 |
TW201542532A (zh) | 2013-07-08 | 2015-11-16 | Bayer Cropscience Ag | 作為殺蟲劑的六員c-n-鍵結之芳基硫化物及芳基亞碸衍生物 |
JP6454348B2 (ja) | 2013-12-19 | 2019-01-16 | サンシャイン・レイク・ファーマ・カンパニー・リミテッドSunshine Lake Pharma Co.,Ltd. | 窒素複素環誘導体およびその医薬品への応用 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3823135A (en) * | 1972-12-26 | 1974-07-09 | Shell Oil Co | Pyrimidone herbicides |
GB9006479D0 (en) * | 1989-04-17 | 1990-05-23 | Ici Plc | Novel compounds |
GB8908638D0 (en) * | 1989-04-17 | 1989-06-01 | Ici Plc | Novel compounds |
GB9022445D0 (en) * | 1990-10-16 | 1990-11-28 | Ici Plc | Heterocyclic compounds |
BR9301666A (pt) * | 1992-04-28 | 1993-11-03 | Sumitomo Chemical Co | Composto,composto intermediario,composicao herbicida,processo para exterminar ervas daninhas indesejadas,uso do dito composto e processo para produzi-lo |
-
1994
- 1994-09-02 DE DE4431218A patent/DE4431218A1/de not_active Withdrawn
-
1995
- 1995-08-21 WO PCT/EP1995/003314 patent/WO1996007647A1/de not_active Application Discontinuation
- 1995-08-21 BR BR9508778A patent/BR9508778A/pt not_active Application Discontinuation
- 1995-08-21 JP JP8509158A patent/JPH10505073A/ja not_active Ceased
- 1995-08-21 KR KR1019970701289A patent/KR100389528B1/ko not_active IP Right Cessation
- 1995-08-21 EP EP95929895A patent/EP0804424A1/de not_active Withdrawn
- 1995-08-21 CN CN95194892A patent/CN1121392C/zh not_active Expired - Fee Related
- 1995-08-21 US US08/793,397 patent/US5877121A/en not_active Expired - Fee Related
- 1995-08-21 MX MX9701569A patent/MX9701569A/es unknown
- 1995-08-21 AU AU33472/95A patent/AU3347295A/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CN1121392C (zh) | 2003-09-17 |
MX9701569A (es) | 1997-05-31 |
JPH10505073A (ja) | 1998-05-19 |
US5877121A (en) | 1999-03-02 |
KR100389528B1 (ko) | 2003-10-04 |
BR9508778A (pt) | 1997-12-23 |
WO1996007647A1 (de) | 1996-03-14 |
DE4431218A1 (de) | 1996-03-07 |
EP0804424A1 (de) | 1997-11-05 |
AU3347295A (en) | 1996-03-27 |
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