CN1253550A - 具有除草作用的苯基-尿嘧啶衍生物 - Google Patents
具有除草作用的苯基-尿嘧啶衍生物 Download PDFInfo
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- CN1253550A CN1253550A CN97180093A CN97180093A CN1253550A CN 1253550 A CN1253550 A CN 1253550A CN 97180093 A CN97180093 A CN 97180093A CN 97180093 A CN97180093 A CN 97180093A CN 1253550 A CN1253550 A CN 1253550A
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- Prior art keywords
- alkyl
- cyano group
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- formula
- amino
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- UIKIQOAXFYAWPW-UHFFFAOYSA-N 5-phenyl-1h-pyrimidine-2,4-dione Chemical class O=C1NC(=O)NC=C1C1=CC=CC=C1 UIKIQOAXFYAWPW-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 230000000694 effects Effects 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 44
- -1 formamyl Chemical group 0.000 claims description 161
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 241000196324 Embryophyta Species 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000011230 binding agent Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000001345 alkine derivatives Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 3
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000003999 initiator Substances 0.000 description 12
- 244000025254 Cannabis sativa Species 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000004702 methyl esters Chemical class 0.000 description 9
- WCFAPJDPAPDDAQ-UHFFFAOYSA-N 1,2-dihydropyrimidine Chemical compound C1NC=CC=N1 WCFAPJDPAPDDAQ-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 241000209140 Triticum Species 0.000 description 8
- 235000021307 Triticum Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 241000209117 Panicum Species 0.000 description 4
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- 241000209072 Sorghum Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000008029 eradication Effects 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000010902 straw Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000801118 Lepidium Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical class CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004176 ammonification Methods 0.000 description 3
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- 239000000706 filtrate Substances 0.000 description 3
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- VMSLCPKYRPDHLN-NRFANRHFSA-N humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)[C@@](O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-NRFANRHFSA-N 0.000 description 3
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- 150000002576 ketones Chemical class 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
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- 239000010695 polyglycol Substances 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
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- 238000005507 spraying Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- 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
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
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- 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
- 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
- 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
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Abstract
本发明涉及式(Ⅰ)的新的苯基-尿嘧啶衍生物。其中R1,R2,R3,R4,R5和n各自如说明书中描述。本发明还涉及多种用于制备所述衍生物的方法和所述衍生物作为除草剂的用途。
Description
本发明涉及新的苯基-尿嘧啶衍生物,其多种制备方法以及其作为除草剂的用途。
一些氰基-苯基-尿嘧啶具有杀昆虫和杀螨性能是已知的(参见EP-A0438209,JP-A05-025142和化学文摘(Chem.Abstr.)119,117269。但是迄今为止还没有描述过这些物质控制杂草的应用。
因此,本发明提供下式新的苯基-尿嘧啶衍生物其中R1 代表氢,氨基或者代表任选被氰基-或卤素-取代的烷基,R2 代表甲酰基,肟基甲基,氰基,羧基,氨基甲酰基,硫代氨基甲酰基或者代表任选被氰基-或卤素-取代的烷基,R3 代表氢,卤素或者代表任选被氰基-或卤素-取代的烷基,R4 代表氰基或硫代氨基甲酰基,R5 代表羟基,巯基,氨基,羟基氨基,氰基,硝基,卤素或者代表下面的基团之一
-R6,-Q-R6,-NH-R6,-NH-O-R6,-NH-SO2-R6,-CQ1-R6,-CQ1-Q2-R6,-CQ1-NH-R6,-Q2-CQ1-R6,-NH-CQ1-R6,-Q2-CQ1-Q2-R6,-NH-CQ1-Q2-R6或-Q2-CQ1-NH-R6其中Q 代表O,S,SO或SO2,Q1和Q2各自独立地代表氧或硫,和R6 代表任选被氰基-,卤素-,烷氧基-,烷硫基-,烷基羰基-,烷氧羰基-或烷基氨基羰基-取代的烷基,代表各种情况下任选被氰基-,羧基-,卤素-,烷基羰基-,烷氧羰基-或烷基氨基羰基-取代的链烯基或炔烃基,代表各种情况下任选被氰基-,羧基-,卤素-,烷基羰基-或烷氧羰基-取代的环烷基或环烷基烷基,代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,烷基-,卤代烷基-,烷氧基-,卤代烷氧基-,烷硫基-,卤代烷硫基-,烷基亚磺酰基-,烷基磺酰基-,烷基氨基-和/或二烷基氨基-取代的芳基或芳基烷基,或者代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,烷基-,卤代烷基-,烷氧基-,卤代烷氧基-,烷硫基-,卤代烷硫基-,烷基亚磺酰基-,烷基磺酰基-,烷基氨基-和/或二烷基氨基-取代的杂环基或杂环基烷基,和n 代表数0,1,2或3。
此外,发现当进行下面反应时得到式(I)的苯基-尿嘧啶衍生物:
a)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(II)的氨基链烯酸酯与式(III)的异氰酸芳基酯反应其中R2和R3各自如上定义,和R 代表烷基,芳基或芳基烷基,其中R4,R5和n各自如上定义,或者
b)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(II)的氨基链烯酸酯与式(IV)的芳基氨基甲酸酯反应其中R,R2和R3各自如上定义,其中R4,R5和n各自如上定义,R7 代表烷基,芳基或芳基烷基,或者
R9-Hal (VII)其中R9 代表烷基,卤代烷基或氰基烷基,和Hal 代表氯,溴或碘,或者
d)在稀释剂存在下,式(Ib)的苯基-尿嘧啶衍生物与硫化氢反应其中R1,R2,R3,R5和n各自如上定义。
最后发现,式(I)的苯基-尿嘧啶衍生物具有非常好的除草性能。
令人惊奇地,本发明式(I)的苯基-尿嘧啶衍生物比具有相同作用的结构最相近的现有技术物质具有好得多的除草活性。
式(I)提供了本发明苯基-尿嘧啶衍生物的一般定义。
在所述定义中,饱和的或不饱和的烃链,例如烷基,链烯基或炔烃基,在各种情况下是直链或支链的,也包括与杂原子组合例如在烷氧基或烷硫基中的情况。
卤素一般代表氟,氯,溴或碘,优选代表氟,氯或溴,特别代表氟或氯。
优选的是式(I)的苯基-尿嘧啶衍生物,其中R1 代表氢,氨基或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R2 代表甲酰基,肟基甲基,氰基,羧基,氨基甲酰基,硫代氨基甲酰基或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R3 代表氢,氟,氯,溴或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R4 代表氰基或硫代氨基甲酰基,R5 代表羟基,巯基,氨基,羟基氨基,氰基,硝基,氟,氯,溴或者代表下面的基团之一
-R6,-Q-R6,-NH-R6,-NH-O-R6,-NH-SO2-R6,-CQ1-R6,-CQ1-Q2-R6,-CQ1-NH-R6,-Q2-CQ1-R6,-NH-CQ1-R6,-Q2-CQ1-Q2-R6,-NH-CQ1-Q2-R6或-Q2-CQ1-NH-R6,其中Q 代表O,S,SO或SO2,Q1和Q2各自独立地代表氧或硫,和R6 代表任选被氰基-,卤素-,C1-C4-烷氧基-,C1-C4-烷硫基-,C1-C4-烷基羰基-,C1-C4-烷氧羰基-或C1-C4-烷基氨基羰基-取代的具有1-6个碳原子的烷基,代表各种情况下任选被氰基-,羧基-,卤素-,C1-C4-烷基羰基-,C1-C4-烷氧羰基-或C1-C4-烷基氨基羰基-取代的每种情况下具有2-6个碳原子的链烯基或炔烃基,代表各种情况下任选被氰基-,羧基-,卤素-,C1-C4-烷基羰基-或C1-C4-烷氧羰基-取代的各种情况下环烷基中具有3-6个碳原子和任选地在烷基部分中具有1-4个碳原子的环烷基或环烷基烷基,代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-烷基氨基-或二甲基氨基-取代的各种情况下芳基中具有6或10个碳原子和任选地烷基部分中具有1-4个碳原子的芳基或芳基烷基,或者代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-烷基氨基-和/或二甲基氨基-取代的在杂环基中具有2-6个碳原子和1-3个氮原子和/或1或2个氧原子和/或一个硫原子和任选地烷基部分中具有1-4个碳原子的杂环基或杂环基烷基,和n 代表数0,1,2或3。
特别优选的是式(I)的苯基-尿嘧啶衍生物,其中R1 代表氢,氨基,甲基或乙基,R2 代表甲酰基,肟基甲基,氰基,羧基,氨基甲酰基,硫代氨基甲酰基或者代表任选被氟-或氯-取代的甲基或乙基,R3 代表氢,氯或者任选被氟-或氯-取代的甲基或乙基,R4 代表氰基或硫代氨基甲酰基,R5 代表羟基,巯基,氨基,羟基氨基,氰基,硝基,氟,氯,溴或者代表下面的基团之一
R6,-Q-R6,-NH-R6,-NH-O-R6,-NH-SO2-R6,-CQ1-R6,-CQ1-Q2-R6,-CQ1-NH-R6,-Q2-CQ1-R6,-NH-CQ1-R6,-Q2-CQ1-Q2-R6,-NH-CQ1-Q2-R6或-Q2-CQ1-NH-R6,其中Q 代表O,S,SO或SO2,Q1和Q2各自独立地代表氧或硫,和R6 代表各种情况下任选被氰基-,氟-,氯-,甲氧基-,乙氧基-,甲硫基-,乙硫基-,乙酰基-,丙酰基-,甲氧羰基-,乙氧羰基-,甲基氨基羰基-或乙基氨基羰基-取代的甲基,乙基,正-或异丙基,正-、异-、仲-或叔-丁基,或者代表各种情况下任选被氰基-,羧基-,氟-,氯-,溴-,乙酰基-,丙酰基-,甲氧羰基-,乙氧羰基-,甲基氨基羰基-或乙基氨基羰基-取代的丙烯基,丁烯基,丙炔基或丁炔基,或者代表各种情况下任选被氰基-,羧基-,氟-,氯-,溴-,乙酰基-,丙酰基-,甲氧羰基-或乙氧羰基-取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基,环己基甲基,或者代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,甲基-,乙基-,正-或异-丙基-,正-、异-、仲-或叔-丁基-,二氟甲基-,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-,甲硫基-,乙硫基-,二氟甲硫基-,三氟甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,甲基氨基-,乙基氨基-和/或二甲基氨基-取代的苯基,苄基或苯基乙基,代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,甲基-,乙基-,正-或异-丙基-,正-、异-、仲-或叔-丁基-,二氯甲基-,三氯甲基-,二氟甲基-,三氟甲基-,氯代二氟甲基-,氟代二氯甲基-,甲氧基-,乙氧基-,正-或异-丙氧基-,二氟甲氧基-,三氟甲氧基-,甲硫基-,乙硫基-,正-或异-丙硫基-,二氟甲硫基-,三氟甲硫基-,氯代二氟甲硫基-,氟代二氯甲硫基-,甲基亚磺酰基-,乙基亚磺酰基-,甲基磺酰基-,乙基磺酰基-,甲基氨基-,乙基氨基-,正-或异-丙基氨基-和/或二甲基氨基-取代的选自环氧乙烷基,噁丁环基,呋喃基,四氢呋喃基,二氧戊环基,噻吩基,四氢噻吩基,吡咯基,吡唑基,咪唑基,三唑基,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,吡唑基甲基,呋喃基甲基,噻吩基甲基,噁唑基甲基,异噁唑基甲基,噻唑基甲基,吡啶基甲基还有嘧啶基甲基的杂环基或杂环基烷基,和n 代表数1或2。
上述一般或优选的基团的定义适用于式(I)的终产物和相应地适用于各种情况下用于制备所需要的起始物或中间体。这些基团的定义可以根据需要相互组合,即包括给定优选的范围之间的组合。
使用3-氨基-丁烯酸甲酯和N-(3-氰基-5-氟-4-三氟甲基-苯基)-氨基甲酸甲酯为起始物,则本发明方法(b)的过程可以通过下面的反应式详细说明:
使用1-(5-氰基-2,4-二氯苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶为起始物和1-氨基氧基-2,4-二硝基-苯为反应组分,则本发明方法(c,变化方法α)的反应过程可以通过下面的反应式详细说明:
使用1-(5-氰基-2,4-二氯苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶为起始物和硫酸二甲酯为反应组分,则本发明方法(c,变化方法β)的反应过程可以通过下面的反应式详细说明:
使用1-(5-氰基-2,4-二氯苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶为起始物和硫化氢为反应组分,则本发明方法(d)的反应过程可以通过下面的反应式详细说明:
式(II)提供了进行本发明方法(a)和(b)需要用作起始物的氨基链烯酸酯的一般定义。在式(II)中,R2和R3优选地或特别地具有上文已经指出的、与描述本发明式(I)的化合物相关的、作为优选的或作为特别优选的R2和R3的那些定义。R优选代表具有1-4个碳原子的烷基,苯基或苄基。特别优选地,R代表甲基,乙基或苯基。
式(II)的起始物是已知的或者可以通过已知的方法制备(参见,杂环化学杂志(J.Heterocycl.Chem.),9(1972),513-522)。
式(III)提供了进行本发明方法(a)需要用作反应组分的异氰酸芳基酯的一般定义。在式(III)中,R4,R5和n各自优选地或特别地具有上文已经指出的、与描述本发明式(I)的化合物相关的、作为优选的或作为特别优选的R4,R5和n的那些定义。
式(III)的起始物是已知的或者可以通过已知的方法制备(参见,四面体通讯(Tetrahedron Lett.)1967,961-962;EP-A0063905,EP-A0093610,EP-A0093620,EP-A0397052和EP-A0572782)。
式(IV)提供了进行本发明方法(b)需要用作反应组分的芳基氨基甲酸酯的一般定义。在式(IV)中,R4,R5和n各自优选地或特别地具有上文已经指出的、与描述本发明式(I)的化合物相关的、作为优选的或作为特别优选的R4,R5和n的那些定义;R7优选代表C1-C4-烷基,苯基或苄基,并且特别代表甲基,乙基或苯基。
式(IV)的芳基氨基甲酸酯是已知的或者可以通过已知的方法制备(参见EP-A0063905)。
因此,如果适当在酸受体例如吡啶的存在下,和如果适当在稀释剂例如二氯甲烷的存在下,在-20℃和+100℃之间的温度下,使式(VIII)苯胺与式(IX)的氯羰基化合物反应来获得式(IV)的芳基氨基甲酸酯其中R4,R5和n各自如上定义,
R7O-CO-Cl (IX),其中R7 如上定义。
进行本发明方法(c)需要用作起始物的式(Ia)的苯基-尿嘧啶衍生物是可以通过本发明方法(a)或(b)制备的本发明化合物。
进行本发明方法(c,变化方法α)需要用作反应组分的式(V)的1-氨基氧基-2,4-二硝基-苯是已知的(参见,杂环化学杂志4(1967),413-414)。
式(VI)提供了进行本发明方法(c,变化方法β)需要用作反应组分的硫酸酯的一般定义。在该结构式中,R8优选代表具有1-4个碳原子的烷基,并且特别优选代表甲基或乙基。
式(VII)提供了当进行本发明方法(c,变化方法β)时也需要用作反应组分的卤代化合物的一般定义。在该结构式中,R9优选代表各种情况下具有1-4个碳原子的烷基,氰基烷基,氟代烷基或氯代烷基。Hal优选代表溴或碘。R9 特别优选代表甲基或乙基。Hal 也特别优选代表溴或碘。
进行本发明方法(d)需要用作起始物的式(Ib)的苯基-尿嘧啶衍生物是可以通过本发明方法(a),(b)或(c)制备的本发明化合物。
进行本发明方法(a)至(c)的合适的酸结合剂是所有常规的无机或有机酸受体。优选使用碱金属或碱土金属乙酸盐,氨化物,碳酸盐,碳酸氢盐,氢化物,氢氧化物或烷氧化物,例如乙酸钠,乙酸钾或乙酸钙,氨化锂,氨化钠,氨化钾或氨化钙,碳酸钠,碳酸钾或碳酸钙,碳酸氢钠,碳酸氢钾或碳酸氢钙,氢化锂,氢化钠,氢化钾或氢化钙,氢氧化锂,氢氧化钠,氢氧化钾或氢氧化钙,甲醇钠,乙醇钠,正-或异-丙醇钠,正-、异-、仲-或叔丁醇钠,或甲醇钾,乙醇钾,正-或异-丙醇钾,正-、异-、仲-或叔丁醇钾;还有碱性有机氮化合物,例如三甲胺,三乙胺,三丙胺,三丁胺,乙基二异丙基胺,N,N-二甲基-环己基胺,二环己基胺,乙基二环己基胺,N,N-二甲基苯胺,N,N-二甲基苄基胺,吡啶,2-甲基-、3-甲基-、4-乙基-、2,4-二甲基-、2,6-二甲基-、3,4-二甲基-和3,5-二甲基-吡啶,5-乙基-2-甲基-吡啶,4-二甲基氨基-吡啶,N-甲基-哌啶,1,4-二氮杂双环[2.2.2]-辛烷(DABCO),1,5-二氮杂双环[4.3.0]-壬-5-烯(DBN)或1,8-二氮杂双环[5.4.0]-十一-7-烯(DBU)。
进行本发明方法(a)和(b)的合适的稀释剂是所有常规惰性有机溶剂。优选使用脂肪族、脂环族或芳香族的任选卤化的烃,例如汽油,苯,甲苯,二甲苯,氯苯,二氯苯,石油醚,己烷,环己烷,二氯甲烷,氯仿,四氯化碳;醚类,例如乙醚,二异丙基醚,二噁烷,四氢呋喃或乙二醇二甲基醚或乙二醇二乙基醚;酮类,例如丙酮,丁酮或甲基异丁基酮;腈类,例如乙腈,丙腈或丁腈;酰胺类,例如N,N-二甲基甲酰胺,N,N-二甲基乙酰胺,N-甲基-N-甲酰苯胺,N-甲基-吡咯烷酮或六甲基磷酰三胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜;醇类,例如甲醇,乙醇,正-或异-丙醇,乙二醇单甲基醚,乙二醇单乙基醚,二甘醇单甲基醚,还有二甘醇单乙基醚。
进行本发明方法(a)和(b)时,反应温度可以在较宽的范围内变化。一般情况下,反应在0℃和200℃之间的温度下进行,优选在10℃和150℃之间的温度下进行。
本发明方法(a)至(c)一般在大气压下进行。但是也可以在高压下操作,或者,如果不使用高挥发性组分,可以在低压下操作。
进行本发明方法(c)的合适的稀释剂是常规用于该类反应的所有惰性有机溶剂。在变化方法(α)的反应中,优选使用质子惰性极性溶剂,例如N,N-二甲基甲酰胺和N-甲基-吡咯烷酮。
在变化方法(β)的反应中,同样优选使用质子惰性极性溶剂,例如丙酮,乙腈,N,N-二甲基甲酰胺和二甲亚砜。
进行本发明方法(c)时,同样可以在一定范围内变化反应温度。在变化方法(α)中,一般情况下,反应在0℃和100℃之间的温度下进行,优选在10℃和50℃之间的温度下进行。在变化方法(β)中,一般情况下,反应在0℃和200℃之间的温度下进行,优选在10℃和120℃之间的温度下进行。
进行本发明方法(d)的合适的稀释剂是常规用于该类反应的所有惰性有机溶剂。优选使用烃,例如甲苯,或者还有有机碱,例如吡啶,三乙胺和三丁胺。
进行本发明方法(d)时,同样可以在一定范围内变化反应温度。一般情况下,反应在0℃和150℃之间的温度下进行,优选在10℃和100℃之间的温度下进行。
进行本发明方法(d)时,如果适当,反应在高压下进行,优选在1和5巴之间的压力下进行。
进行本发明方法(a)至(d)时,一般以大约等摩尔量使用起始物。但是,也可以以相对大的过量使用其中之一反应组分。反应一般在合适的稀释剂中在酸结合剂存在下进行,并且反应混合物一般在需要的温度下搅拌数小时。通过常规方法进行后处理(参见制备实施例)。
本发明式(I)的苯基-尿嘧啶衍生物具有强的除草活性。另外它们也为重要的农作物例如小麦所耐受。
本发明活性化合物可以用作脱叶剂,干燥剂,杀稻草剂,特别是作为杀杂草剂。从广义上说,所谓杂草被理解是在其所不期望的地点生长的所有植物。本发明物质是作为灭生性除草剂还是选择性除草剂主要取决于使用的量。
与例如下面的植物相关,可以使用本发明活性化合物:双子叶杂草种类:芥属(Sinapis),独行菜属(Lepidium),猪殃殃属(Galium),繁缕属(Stellaria),母菊属(Matricaria),春黄菊属(Anthemis),辣子草(Galinsoga),藜属(Chenopodium),荨麻属(Urtica),千里光属(Senecio),苋属(Amaranthus),马齿苋属(Portulaca),苍耳属(Xanthium),旋花属(Convolvulus),甘薯属(Ipomoea),蓼属(Polygonum),田菁(Sesbania),豚草属(Ambrosia),蓟属(Cirsium),飞廉属(Carduus),苦苣菜属(Sonchus),茄属(Solanum),焊菜属(Rorippa),水松叶属(Rotala),母草属(Lindernia),野芒麻属(Lamium),婆婆纳属(Veronica),苘麻属(Abutilon),刺果(Emex),曼陀罗属(Datura),堇菜属(Viola),鼬瓣花属(Galeopsis),罂粟属(Papaver),矢车菊属(Centaurea),车轴草属(Trifolium),毛茛属(Ranunculus)和蒲公英属(Taraxacum)。双子叶作物种类:棉属(Gossypium),大豆属(Glycine),Beta,胡萝卜属(Daucus),菜豆属(Phaseolus),豌豆属(Pisum),茄属(Solanum),亚麻属(Linum),甘薯属(Ipomoea),巢菜属(Vicia),烟草属(Nicotiana),番茄属(Lycopersicon),花生(Arachis),芥属(Brassica),莴苣属(Lactuca),香瓜属(Cucumis),和臭瓜(Cucurbita)。单子叶杂草种类:稗属(Echinochloa),狗尾草属(Setaria),黍属(Panicum),马唐属(Digitaria),梯牧属(Phleum),早熟禾属(Poa),羊茅属(Festuca),蟋蟀菜属(Eleusine),臂形草属(Brachiaria),黑麦草属(Lolium),雀麦属(Bromus),燕麦属(Avena),莎草属(Cyperus),蜀黍属(Sorghum),冰草属(Agropyron),Cynodon,雨久花属(Monchoria),飘拂草属(Fimbristylis),慈姑(Sagittaria),荸荠属(Eleocharis),镳草(Scirpus),雀稗草(Paspalum),Ischaemum,尖瓣花属(Sphenoclea),龙爪茅属(Dactyloctenium),剪股颍属(Agrostis),看麦娘属(Alopecurus)和Apera。
单子叶作物种类:稻属(Oryza),玉米属(Zea),小麦属(Triticum),大麦属(Hordeum),燕麦属(Avena),黑麦属(Secale),蜀黍属(Sorghum),黍属(Panicum),甘蔗(Saccharum),菠萝(Ananas),天门冬属(Asparagus)和葱属(Allium)。
但是本发明活性化合物的用途不受这些种类的限制,而是以相同的方式扩展到其它植物。
根据浓度,本发明化合物适于例如在工业场所和铁道,有或没有树木的路或广场上全部控制杂草。这些化合物同样被用来在多年生种植植物场所,草坪,运动场和牧场控制杂草,所述多年生种植植物场所例如树林,装饰性种植的树,果园,葡萄园,柠檬园,坚果园,香蕉种植园,咖啡种植园,茶种植园,橡胶种植园,油棕种植园,可可种植园,软果种植植物和蛇麻草田,以及用来在年生种植植物场所选择性控制杂草。
本发明的式(I)化合物特别适用于在芽前和芽后在单子叶农作物中选择性控制单子叶和双子叶杂草。
活性化合物可以配制成常规制剂,例如溶液、乳剂、可湿性粉末、悬浮剂、粉剂、细粉剂、糊剂、可溶性粉末、颗粒剂、混悬乳油和浸有活性化合物的天然和合成材料,以及包裹在聚合物中的细微胶囊。
这些型剂是用已知的方式生产的,例如,通过将活性化合物与扩充剂即液体溶剂和/或固体载体混合,并任选使用表面活性剂,即乳化剂和/或分散剂和/或起泡剂。
如果使用的扩充剂是水,则也可以用例如有机溶剂作助溶剂。合适的液体溶剂主要有:芳族化合物,如二甲苯,甲苯或烷基萘,氯代芳族化合物和氯代脂肪烃,如氯代苯类、氯乙烯类或二氯甲烷,脂肪烃,如环己烷或石蜡,例如矿物油馏份,矿物油和植物油,醇类,如丁醇或乙二醇以及其醚和酯,酮类,如丙酮、甲乙酮、甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体载体是:例如铵盐和磨碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土,和磨碎的合成矿物质,如高分散二氧化硅、矾土和硅酸盐;用于颗粒剂的适合的固体载体有:例如压碎和破碎的天然矿物质如方解石、大理石、浮石、海泡石和白云石,以及有机和无机粉的合成颗粒,和如下有机物的颗粒:例如锯木屑、椰壳、玉米穗轴和烟茎;适合的乳化剂和/或起泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚,例如,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;适合的分散剂有:例如,木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物,如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂,如脑磷脂和卵磷脂,和合成磷脂。其它可能的添加剂是矿物油和植物油。
也可以使用染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料,如茜素染料、偶氮染料和金属酞菁染料,和微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
一般情况下,制剂含有0.1-95%重量的活性化合物,优选0.5-90%。
对于控制杂草,可以使用本发明活性化合物本身或其制剂形式,也可以作为与已知除草剂的混合物,可以是最终制剂或容器混合物。
适用于所述混合物的可能的成分是已知的除草剂,例如乙草胺,三氟羧草醚(-钠盐),苯草醚,甲草胺,禾草灭(钠盐),莠灭净,amidochlor,amidosulfuron,磺草灵,莠去津,azimsulfuron,除草灵,呋草黄,苄嘧草隆(-甲酯),灭草松,吡草酮,新燕灵(-乙酯),双丙氨酰膦,甲羧除草醚,溴丁酰草胺,溴酚肟,溴苯腈,丁草胺,丁草特,cafenstrole,卡草胺,甲氧除草醚,灭草平,杀草敏,氯嘧黄隆(-乙酯),草枯醚,氯黄隆,氯麦隆,环庚草醚,醚草隆,烯草酮,clodinafop(-propargyl),异噁草酮,二氯吡啶酸,clopyrasulfuron,cloransulam(-methyl),cumyluron,氰草津,灭草特,cyclosulfamuron,噻草酮,cyhalofop(-butyl),2,4-滴,2,4-滴丁酸,2,4-滴丙酸,甜菜安,燕麦敌,麦草畏,禾草灵(-甲酯),双苯唑快,吡氟草胺,丁噁隆,哌草丹,二甲草胺,二甲丙乙净,dimethenamid,氨基乙氟灵,双苯酰草胺,敌草快,氟硫草定,敌草隆,杀草隆,EPTC,禾草畏,乙丁烯氟灵,ethametsulfuron(-methyl),乙呋草黄,ethoxyfen,etobenzanid,噁唑禾草灵,麦草伏(-异丙酯),麦草伏(-异丙酯-L),麦草伏(-甲酯),啶嘧黄隆,吡氟禾草灵(-丁酯),flumetsulam,flumiclorac(-pentyl),flumioxazin,flumipropyn,伏草隆,氟咯草酮,乙羧氟草醚(-乙酯),胺草唑,flupropacil,芴丁酸,氟定酮,氟草烟,调嘧醇,呋草酮,氟黄胺草醚,草铵膦(-铵盐),草甘膦(-异丙基铵盐),halosafen,吡氟氯禾灵(-乙氧基乙酯),环嗪酮,咪草酯(-甲酯),imazamethapyr,imazamox,灭草烟,灭草喹,咪草烟,imazosulfuron,碘苯腈,异丙乐灵,异丙隆,isoxaben,isoxaflutole,噁草醚,乳氟禾草灵,环草定,利谷隆,MCPA,MCPP,苯噻草胺,苯嗪草酮,吡草安,甲基苯噻隆,metobenzuron,秀谷隆,丙草安,metosulam,甲氧隆,嗪草酮,甲黄隆(-甲酯),嗪草酮,草达灭,绿谷隆,萘丙胺,萘氧丙草胺,草不隆,烟嘧黄隆,哒草伏,坪草丹,安磺灵,噁草酮,乙氧氟草醚,百草枯,二甲戊乐灵,甜菜宁,哌草磷,丙草安,氟嘧黄隆(-甲酯),扑草净,毒草安,敌稗,喔草酯,戊炔草胺,苄草丹,prosulfuron,吡唑特,吡嘧黄隆(-乙酯),苄草唑,稗草畏,哒草特,pyrithiobac(-sodium),二氯喹啉酸,喹草酸,喹禾灵(-乙酯),喹禾灵(-四氢糠基酯),rimsulfuron,稀禾定,西玛津,西草净,sulcotrione,sulfentrazone,嘧黄隆(-甲酯),草甘膦,牧草胺,特丁噻草隆,特丁津,特丁净,thenylchlor,thiafluamide,thiazopyr,thidiazimin,噻黄隆(-甲酯),杀草丹,仲草丹,肟草酮,野燕畏,醚苯黄隆,苯黄隆(-甲酯),绿草定,灭草环,氟乐灵和triflusulfuron。
也可能是与其它已知活性化合物的混合物,所述其它活性化合物是例如杀真菌剂,杀昆虫剂,杀螨剂,杀线虫剂,鸟驱避剂,植物营养剂和改善土壤结构的试剂。
这些活性化合物可以使用其本身,以其制剂形式使用,或者以通过进一步稀释而从中制备的使用形式使用,例如即用型溶液,混悬剂,乳剂,粉剂,糊剂和颗粒剂。它们可以以常规方式使用,例如通过浇灌,喷雾,弥雾或播撒。
本发明活性化合物可以在植物芽前或芽后施用。其也可以在播种前掺合到土壤中。
使用的活性化合物的量可以在一个宽的范围内变化。这主要取决于期望的效果的性质。一般情况下,使用的量是每公顷土壤面积使用1g-10kg活性化合物,优选每公顷土壤面积使用5g-5kg活性化合物。
用分水器将8.1g(27mmol)3-氨基-4,4,4-三氟-丁烯酸乙酯,7.5g碳酸钾和100ml N-甲基-吡咯烷酮的混合物加热1小时,然后加入7.0g(27mmol)N-(5-氰基-2,4-二氯-苯基)-O-乙基-氨基甲酸酯,并且反应混合物在130℃再搅拌4小时,冷却到室温后,用大约相同体积量的水和乙酸乙酯将混合物稀释到其原体积的大约4倍,并且用浓盐酸酸化至大约pH3。充分振荡混合物后分离出有机相,水相用乙酸乙酯萃取,合并的有机相用硫酸钠干燥并过滤。用水泵真空从滤液中小心蒸馏出溶剂。
首先将2.0g(5.7mmol)1-(5-氰基-2,4-二氯-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶和0.5g碳酸氢钠加入到50mlN,N-二甲基甲酰胺中,加入0.6g(3mmol)1-氨基-氧基-2,4-二硝基-苯后,反应混合物在室温下搅拌5小时。再加入0.6g(3mmol)1-氨基氧基-2,4-二硝基-苯后,反应混合物在室温下再搅拌3天。混合物用饱和的氯化钠水溶液稀释后用乙酸乙酯萃取,有机相用硫酸钠干燥并通过硅胶吸滤。水泵真空下浓缩滤液,并且通过柱色谱纯化残余物(硅胶,乙酸乙酯)。
将2.4g(6.9mmol)1-(5-氰基-2,4-二氯-苯基)-3,6-二氢-2,6-二氧代-4-三氟甲基-1(2H)-嘧啶,0.9g(6.9mmol)硫酸二甲酯,0.6g碳酸氢钠和100ml丙酮的混合物在回流下加热18小时。再加入0.2g硫酸二甲酯后,混合物在回流下再加热3小时,再加入0.5ml硫酸二甲酯后,再加热18小时。然后水泵真空下浓缩混合物。残余物用水/乙酸乙酯振荡。有机相用硫酸钠干燥并过滤。水泵真空下浓缩滤液,残余物通过用二异丙醚消化而结晶,并且通过吸滤分离产物。
得到0.6g(理论量的24%)的1-(5-氰基-2,4-二氯-苯基)-3,6-二氢-2,6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶,熔点是161℃。
使用上述方法,也可以制备例如下面表中结构式所示的化合物。表1
应用实施例实施例A芽前试验溶剂:5份重量丙酮乳化剂:1份重量烷基芳基聚乙二醇醚
实施例序号 | R1 | R2 | R3 | (位置)R4 | (位置)R5 | n | 物理数据 |
4 | H | CF3 | H | (5-)CN | (2-)F,(4-)NHSO2CH3 | 2 | mp.:236℃ |
5 | CH3 | CF3 | H | (5-)CN | (2-)F,(4-)NHSO2CH3 | 2 | mp.:199℃ |
6 | CH3 | CF3 | H | (5-)CN | (2-)F,(4-)CN | 2 | mp.:148℃ |
7 | H | CF3 | H | (5-)CN | (2)OH,(4)-Cl | 2 | mp.:279℃ |
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
在正常土壤中播种试验植物的种子。24小时后,用活性化合物制剂浇灌土壤。每单位面积水的量保持不变是有利的。制剂中活性化合物的浓度并不关键,只有每单位面积活性化合物的施用比例是重要的。
三星期后,以与未处理对照物生长相比较的伤害百分率评价对植物伤害的程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏
在该项试验中,以60-250g/ha的施用比例时,实施例2,3和6所列的本发明化合物显示出80%或更强的除不同杂草的药效,并且小麦对其有好的耐受性。实施例B芽后试验溶剂:5份重量丙酮乳化剂:1份重量烷基芳基聚乙二醇醚
为了制备活性化合物合适的制剂,将1份重量活性化合物与所述量溶剂混合,加入所述量乳化剂,用水将乳油稀释到需要的浓度。
用活性化合物制剂对高5-15cm的试验植物喷雾,使对每单位面积施用特定量的期望的活性化合物。选择喷雾液的浓度,使以1000L水/公顷施用特定量的期望的活性化合物。
三星期后,以与未处理对照物生长相比较的伤害百分率评价对植物的伤害程度。数据说明:
0%=没有效果(象未处理对照物一样)
100%=完全破坏
在该项试验中,以60-2000g/ha的施用比例时,实施例2,3和6所列的本发明化合物显示出80%或更强的除不同杂草的药效。
Claims (7)
1.通式(I)的苯基-尿嘧啶衍生物:其中R1 代表氢,氨基或者代表任选被氰基-或卤素-取代的烷基,R2 代表甲酰基,肟基甲基,氰基,羧基,氨基甲酰基,硫代氨基甲酰基或者代表任选被氰基-或卤素-取代的烷基,R3 代表氢,卤素或者代表任选被氰基-或卤素-取代的烷基,R4 代表氰基或硫代氨基甲酰基,R5 代表羟基,巯基,氨基,羟基氨基,氰基,硝基,卤素或者代表下面的基团之一
-R6,-Q-R6,-NH-R6,-NH-O-R6,-NH-SO2-R6,-CQ1-R6,-CQ1-Q2-R6,-CQ1-NH-R6,-Q2-CQ1-R6,-NH-CQ1-R6,-Q2-CQ1-Q2-R6,-NH-CQ1-Q2-R6或-Q2-CQ1-NH-R6,其中Q 代表O,S,SO或SO2,Q1和Q2各自独立地代表氧或硫,和R6 代表任选被氰基-,卤素-,烷氧基-,烷硫基-,烷基羰基-,烷氧羰基-或烷基氨基羰基-取代的烷基,代表各种情况下任选被氰基-,羧基-,卤素-,烷基羰基-,烷氧羰基-或烷基氨基羰基-取代的链烯基或炔烃基,代表各种情况下任选被氰基-,羧基-,卤素-,烷基羰基-或烷氧羰基-取代的环烷基或环烷基烷基,代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,烷基-,卤代烷基-,烷氧基-,卤代烷氧基-,烷硫基-,卤代烷硫基-,烷基亚磺酰基-,烷基磺酰基-,烷基氨基-和/或二烷基氨基-取代的芳基或芳基烷基,或者代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,烷基-,卤代烷基-,烷氧基-,卤代烷氧基-,烷硫基-,卤代烷硫基-,烷基亚磺酰基-,烷基磺酰基-,烷基氨基-和/或二烷基氨基-取代的杂环基或杂环基烷基,和n代表数0,1,2或3。
2.权利要求1的式(I)的苯基-尿嘧啶衍生物,其中R1 代表氢,氨基或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R2 代表甲酰基,肟基甲基,氰基,羧基,氨基甲酰基,硫代氨基甲酰基或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R3 代表氢,氟,氯,溴或者代表任选被氰基-,氟-或氯-取代的具有1-4个碳原子的烷基,R4 代表氰基或硫代氨基甲酰基,R5 代表羟基,巯基,氨基,羟基氨基,氰基,硝基,氟,氯,溴或者代表下面的基团之一
-R6,-Q-R6,-NH-R6,-NH-O-R6,-NH-SO2-R6,-CQ1-R6,-CQ1-Q2-R6,-CQ1-NH-R6,-Q2-CQ1-R6,-NH-CQ1-R6,-Q2-CQ1-Q2-R6,-NH-CQ1-Q2-R6或-Q2-CQ1-NH-R6,其中Q 代表O,S,SO或SO2,Q1和Q2各自独立地代表氧或硫,和R6 代表任选被氰基-,卤素-,C1-C4-烷氧基-,C1-C4-烷硫基-,C1-C4-烷基羰基-,C1-C4-烷氧羰基-或C1-C4-烷基氨基羰基-取代的具有1-6个碳原子的烷基,代表各种情况下任选被氰基-,羧基-,卤素-,C1-C4-烷基羰基-,C1-C4-烷氧羰基-或C1-C4-烷基氨基羰基-取代的每种情况下具有2-6个碳原子的链烯基或炔烃基,代表各种情况下任选被氰基-,羧基-,卤素-,C1-C4-烷基羰基-或C1-C4-烷氧羰基-取代的各种情况下环烷基中具有3-6个碳原子和任选地在烷基部分中具有1-4个碳原子的环烷基或环烷基烷基,代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-烷基氨基-或二甲基氨基-取代的各种情况下芳基中具有6或10个碳原子和任选地烷基部分中具有1-4个碳原子的芳基或芳基烷基,或者代表各种情况下任选被羟基-,巯基-,氨基-,氰基-,羧基-,氨基甲酰基-,硫代氨基甲酰基-,C1-C4-烷基-,C1-C4-卤代烷基-,C1-C4-烷氧基-,C1-C4-卤代烷氧基-,C1-C4-烷硫基-,C1-C4-卤代烷硫基-,C1-C4-烷基亚磺酰基-,C1-C4-烷基磺酰基-,C1-C4-烷基氨基-和/或二甲基氨基-取代的在杂环基中具有2-6个碳原子和1-3个氮原子和/或1或2个氧原子和/或一个硫原子和任选地烷基部分中具有1-4个碳原子的杂环基或杂环基烷基,和n 代表数0,1,2或3。
3.制备权利要求1的式(I)苯基-尿嘧啶衍生物的方法,特征在于
a)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(II)的氨基链烯酸酯与式(III)的异氰酸芳基酯反应其中R2和R3各自如上定义和R 代表烷基,芳基或芳基烷基,其中R4,R5和n各自如上定义,或者
b)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,式(II)的氨基链烯酸酯与式(IV)的芳基氨基甲酸酯反应其中R,R2和R3各自如上定义,其中R4,R5和n各自如上定义,R7 代表烷基,芳基或芳基烷基,或者
α)如果适当在酸结合剂存在下和如果适当在稀释剂存在下,与式(V)的1-氨基氧基-2,4-二硝基苯反应,或者
R9-Hal (VII)其中R9代表烷基,卤代烷基或氰基烷基,和Hal代表氯,溴或碘,或者
4.除草组合物,特征在于,其含有至少一种权利要求1的式(I)的苯基-尿嘧啶衍生物。
5.权利要求1的式(I)的苯基-尿嘧啶衍生物防治不期望植物的用途。
6.控制杂草的方法,特征在于,使权利要求1的式(I)的苯基-尿嘧啶衍生物作用于杂草和/或其生长地域。
7.制备除草组合物的方法,特征在于,将权利要求1的式(I)的苯基-尿嘧啶衍生物与扩充剂和/或表面活性剂混合。
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AU2328188A (en) * | 1987-09-23 | 1989-04-18 | Ciba-Geigy Ag | Heterocyclic compounds |
US5041156A (en) * | 1987-10-22 | 1991-08-20 | Ciba-Geigy Corporation | 3-aryluracils for the control of weeds |
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AU627906B2 (en) * | 1989-07-14 | 1992-09-03 | Nissan Chemical Industries Ltd. | Uracil derivatives and herbicides containing the same as active ingredient |
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