CN1103764C - 取代的苯基尿嘧啶 - Google Patents
取代的苯基尿嘧啶 Download PDFInfo
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- CN1103764C CN1103764C CN97195075A CN97195075A CN1103764C CN 1103764 C CN1103764 C CN 1103764C CN 97195075 A CN97195075 A CN 97195075A CN 97195075 A CN97195075 A CN 97195075A CN 1103764 C CN1103764 C CN 1103764C
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 16
- -1 thiocarbamoyl Chemical group 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 51
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
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- 125000003302 alkenyloxy group Chemical group 0.000 abstract description 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 abstract description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000001769 aryl amino group Chemical group 0.000 abstract description 2
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- 125000003277 amino group Chemical group 0.000 abstract 2
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- 239000002253 acid Substances 0.000 description 7
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- 235000007232 Matricaria chamomilla Nutrition 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
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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- 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
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Abstract
本发明涉及通式(I)新的取代的苯基尿嘧啶：其中R1代表氢，卤素或任选被取代的烷基，R2代表任选被取代的烷基，R3代表氢，氨基或者代表烷基，链烯基或炔烃基，其各自任选被取代，R4代表氢，氰基或卤素，R5代表氰基或硫代氨基甲酰基，和R6代表下面的基团之一：其中Q1和Q2各自代表氧或硫，R7在每种情况下代表氢或任选被取代的烷基，R8代表氢，羟基，氨基或者代表烷基，烷氧基，烷基氨基，二烷基氨基，烷基羰基氨基，烷基磺酰基氨基，链烯基，链烯基氧基，炔烃基，环烷基，环烷基氧基，环烷基氨基，环烷基羰基氨基，环烷基磺酰基氨基，芳基，芳基氧基，芳基氨基，芳基羰基氨基，芳基磺酰基氨基，芳基烷基，芳基烷氧基，芳基烷基氨基，其中各基团任选被取代，和R9和R10各自代表烷基，并且涉及其制备方法，以及涉及其作为除草剂的用途。
Description
技术领域
本发明涉及新的取代的苯基尿嘧啶，其制备方法，以及其作为除草剂的用途。
背景技术
已知一些取代的尿嘧啶具有除草性质(参见DE 4131038，DE4237920，DE4329537，EP 408382/US 5084084/US 5127935/US 5154755，EP 542685，EP 563384，EP 648749，US 4979982，US 5169430，WO91/00278，WO 95/25725)。但是，迄今为止这些化合物还没有获得任何重要的有价值的陈述。
发明内容
因此，本发明提供通式(I)新的取代的苯基尿嘧啶：
其中R1代表氢，卤素或任选被取代的烷基，R2代表任选被取代的烷基，R3代表氢，氨基或者代表烷基，链烯基或炔烃基，其各自任选被取代，R4代表氢，氰基或卤素，R5代表氰基或硫代氨基甲酰基，和R6代表下面的基团之一：
其中Q1和Q2各自代表氧或硫，R7在每种情况下代表氢或任选被取代的烷基，R8代表氢，羟基，氨基或者代表烷基，烷氧基，烷基氨基，二烷基氨基，烷基羰基氨基，烷基磺酰基氨基，链烯基，链烯基氧基，炔烃基，环烷基，环烷基氧基，环烷基氨基，环烷基羰基氨基，环烷基磺酰基氨基，芳基，芳基氧基，芳基氨基，芳基羰基氨基，芳基磺酰基氨基，芳基烷基，芳基烷氧基，芳基烷基氨基，其中各基团任选被取代，并且R9和R10各自代表烷基。
当进行下面的反应时得到了通式(I)新的取代的苯基尿嘧啶：(a)如果适当在稀释剂存在下和如果适当在反应助剂存在下，通式(II)的链烯基苯基尿嘧啶与臭氧反应，
其中R1，R2，R3，R4，R5和R7各自如上定义，和R11和R12各自代表氢，氰基，羧基或者代表各自任选被取代的烷基或烷氧羰基，或者(b)如果适当在稀释剂存在下和如果适当在反应助剂存在下，通式(Ia)羰基苯基尿嘧啶与通式(III)氨基化合物，或与式(III)化合物的酸加成物反应，其中R1，R2，R3，R4，R5和R7各自如上定义，
H2N-R8 (III)其中R8如上定义，或者(c)如果适当在稀释剂存在下和如果适当在反应助剂存在下，通式(Ia)羰基苯基尿嘧啶与通式(IVa)或(IVb)醇和/或硫醇反应，
其中R1，R2，R3，R4，R5和R7各自如上定义，
HQ1R9 (IVa) HQ2R10 (IVb)其中Q1，Q2，R9和R10各自如上定义。
通式(I)化合物也可以根据上述定义应用其它常规方法转化成其它通式(I)化合物，例如通过胺化作用和/或烷基化作用(例如R3：H→NH2，H→CH3)，通过与硫化氢反应(例如R5：CN→CSNH2)。
通式(I)新的取代的苯基尿嘧啶具有强的除草活性。
在上述定义中，饱和的或不饱和的烃链，例如烷基，链烯基或炔烃基在每种情况下是直链或支链的。
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。
本发明优选提供下列式(I)化合物，其中R1代表氢，氟，氯，溴或任选被氟-和/或氯-取代的C1-C4-烷基，R2代表任选被氟-和/或氯-取代的C1-C4-烷基，R3代表氢，氨基，代表任选被氰基-，氟-，氯-或C1-C4-烷氧基-取代的C1-C6-烷基，或者代表任选被氟-和/或氯-取代的C2-C6-链烯基或C2-C6-炔烃基，R4代表氢，氰基，氟或氯，R5代表氰基或硫代氨基甲酰基，和R6代表下面的基团之一：其中Q1和Q2各自代表氧或硫，R7在每种情况下代表氢或代表任选被卤素-或C1-C4-烷氧基-取代的C1-C4-烷基，R8代表氢，羟基，氨基，代表C1-C6-烷基，C1-C6-烷氧基，C1-C6-烷基氨基，二-(C1-C4-烷基)-氨基，C1-C4-烷基羰基氨基或C1-C4-烷基磺酰基氨基，其中各基团任选被卤素，C1-C4-烷氧基或C1-C4-烷氧羰基取代，代表C2-C6-链烯基，C2-C6-烯基氧基，C2-C6-炔烃基，其中各基团任选被卤素取代，代表C3-C6-环烷基，C3-C6-环烷基氧基，C3-C6-环烷基氨基，C3-C6-环烷基羰基氨基或C3-C6-环烷基磺酰基氨基，其中各基团任选被卤素或C1-C4-烷基取代，或者代表苯基，苯氧基，苯基氨基，苯基羰基氨基，苯基磺酰基氨基，苯基-C1-C4-烷基，苯基-C1-C4-烷氧基，苯基-C1-C4-烷基氨基，其中各基团任选被卤素，C1-C4-烷基，C1-C4-卤代烷基，C1-C4-烷氧基或C1-C4-卤代烷氧基取代，并且R9和R10各自代表C1-C4-烷基。
具体实施方式
本发明特别涉及下列式(I)化合物，其中R1代表氢，氟，氯，溴或任选被氟-和/或氯-取代的甲基或乙基，R2代表任选被氟-和/或氯-取代的甲基或乙基，R3代表氢，氨基，代表各自任选被氰基-，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，或者代表任选被氟-和/或氯-取代的丙烯基，丁烯基，丙炔基或丁炔基，R4代表氢，氟或氯，R5代表氰基或硫代氨基甲酰基，和R6代表下面的基团之一：
其中Q1和Q2各自代表氧或硫，R7在每种情况下代表氢或代表各自任选被氟，氯，甲氧基或乙氧基取代的甲基或乙基，R8代表氢，羟基，氨基，代表甲基，乙基，正-或异-丙基，正-、异-、仲或叔-丁基，甲氧基，乙氧基，正-或异-丙氧基，正-、异-、仲或叔-丁氧基，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，乙酰基氨基，丙酰基氨基，正-或异-丁酰基氨基，甲基磺酰基氨基或乙基磺酰基氨基，其中各基团任选被氟，氯，甲氧基，乙氧基，甲氧羰基或乙氧羰基取代，代表丙烯基，丁烯基，丙烯基氧基，丁烯基氧基，丙炔基或丁炔基，其中各基团任选被氟，氯或溴取代，代表环戊基，环己基，环戊基氧基，环己基氧基，环戊基氨基，环己基氨基，环丙基羰基氨基，环丁基羰基氨基，环戊基羰基氨基，环己基羰基氨基，环丙基磺酰基氨基，环丁基磺酰基氨基，环戊基磺酰基氨基或环己基磺酰基氨基，其中各基团任选被氟，氯，溴，甲基或乙基取代，或者代表苯基，苯基氨基，苯基羰基氨基，苯基磺酰基氨基，苄基，苄基氧基或苄基氨基，其中各基团任选被氟，氯，溴，甲基，乙基，三氟甲基，甲氧基，乙氧基，二氟甲氧基或三氟甲氧基取代，和R9和R10各自代表甲基或乙基。
上述一般或优选的基团的定义适用于式(I)终产物和相应适用于用于制备的各种情况下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，即包括指出的优选的范围之间的组合。
根据本发明的式(I)化合物的实例在下面的组中列出。第1组 R6在这种情况下具有例如下面给出的定义：甲酰基，乙酰基，甲基亚氨基甲基，乙基亚氨基乙基，正丙基亚氨基甲基，异丙基亚氨基甲基，肟基甲基，甲氧亚氨基甲基，乙氧亚氨基甲基，正丙氧亚氨基甲基，异丙氧亚氨基甲基，正丁氧亚氨基甲基，1-甲氧亚氨基-乙基，甲氧羰基甲氧亚氨基甲基，乙氧羰基甲氧亚氨基甲基，1-甲氧羰基甲氧亚氨基-乙基，1-乙氧羰基甲氧亚氨基-乙基，1，2-亚肼代亚氨基甲基，甲基1，2-亚肼代亚氨基甲基，二甲基1，2-亚肼代亚氨基甲基，乙酰基1，2-亚肼代亚氨基甲基，甲基磺酰基1，2-亚肼代亚氨基甲基，烯丙氧亚氨基甲基，环戊基氧亚氨基甲基，环己基氧亚氨基甲基，苄基氧亚氨基甲基，环戊基1，2-亚肼代亚氨基甲基，环己基1，2-亚肼代亚氨基甲基，苯基1，2-亚肼代亚氨基甲基，苯基羰基1，2-亚肼代亚氨基甲基，苯基磺酰基1，2-亚肼代亚氨基甲基，苄基1，2-亚肼代亚氨基甲基，二甲氧基甲基，二乙氧基甲基。第2组 R6在这种情况下具有例如上面第1组中给出的意义。第3组 
R6在这种情况下具有例如上面第1组中给出的意义。第4组 R6在这种情况下具有例如上面第1组中给出的意义。第5组 R6在这种情况下具有例如上面第1组中给出的意义。第6组 R6在这种情况下具有例如上面第1组中给出的意义。。第7组 
R6在这种情况下具有例如上面第1组中给出的意义。第8组 
R6在这种情况下具有例如上面第1组中给出的意义。第9组 R6在这种情况下具有例如上面第1组中给出的意义。第10组 R6在这种情况下具有例如上面第1组中给出的意义。第11组 
R6在这种情况下具有例如上面第1组中给出的意义。第12组 R6在这种情况下具有例如上面第1组中给出的意义。第13组 R6在这种情况下具有例如上面第1组中给出的意义。第14组 
R6在这种情况下具有例如上面第1组中给出的意义。第15组 R6在这种情况下具有例如上面第1组中给出的意义。第16组 R6在这种情况下具有例如上面第1组中给出的意义。第17组 
R6在这种情况下具有例如上面第1组中给出的意义。第18组 R6在这种情况下具有例如上面第1组中给出的意义。第19组 R6在这种情况下具有例如上面第1组中给出的意义。第20组 
R6在这种情况下具有例如上面第1组中给出的意义。第21组 
R6在这种情况下具有例如上面第1组中给出的意义。第22组 
R6在这种情况下具有例如上面第1组中给出的意义。
使用例如1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和臭氧为起始物，则本发明方法(a)的反应过程可以通过下面的反应式来说明：
使用例如1-[4-氰基-2-氟-5-甲酰基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和O-甲基-羟基胺为起始物，则本发明方法(b)的反应过程可以通过下面的反应式来说明：
使用例如1-[4-氰基-2-氟-5-甲酰基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和甲醇为起始物，则本发明方法(c)的反应过程可以通过下面的反应式来说明：
式(II)提供了为了制备通式(I)的化合物而在本发明方法(a)中用作起始物的链烯基苯基尿嘧啶的通式定义。在式(II)中，R1，R2，R3，R4，R5和R7各自优选地或特别地具有上文已经指出的，与说明根据本发明制备的式(I)化合物相关的，作为优选的或特别优选的R1，R2，R3，R4，R5和R7的定义；R11和R12优选代表氰基，羧基或C1-C4-烷氧羰基。
式(II)起始物迄今为止还未在文献中公开；作为新的物质，其构成先前技术但是没有预先公开的申请(参见DE 19 528 186)的一个主题。
如果适当在稀释剂存在下，例如在水，乙酸，乙腈和二氯甲烷的存在下，在-20℃和+10℃之间的温度下，当通式(V)氨基苯基尿嘧啶
其中R1，R2，R3，R4和R5各自如上定义，或式(V)化合物的酸加成物与碱金属亚硝酸盐或亚硝酸烷基酯，例如亚硝酸钠，亚硝酸钾，亚硝酸甲酯，亚硝酸正丁酯或叔丁酯，和与卤化氢(HX1)，例如氯化氢或溴化氢，或者金属卤化物，例如氯化铜(I)或氯化铜(II)反应，并且，得到的通式(VI)重氮盐在卤化氢(HX1)存在下，例如在氯化氢或溴化氢存在下，如果适当在水存在和如果适当在最初使用的有机溶剂的存在下，在0℃和50℃之间的温度下，与通式(VII)丙烯酸衍生物反应(接原文pp.18
其中R1，R2，R3，R4和R5各自如上定义，X1代表卤素，
R7CH＝C(R11，R12) (VII)其中R7，R11和R12各自如上定义，并且，得到的产物在稀释剂存在下，例如在N，N-二甲基甲酰胺存在下，在0℃和100℃之间的温度下，与酸受体例如氢化钠反应，得到通式(II)链烯基苯基尿嘧啶(参见制备实施例)。
式(Ia)提供了为了制备通式(I)的化合物而在本发明方法(b)和(c)中用作起始物的羰基苯基尿嘧啶的通式定义。在式(Ia)中，R1，R2，R3，R4，R5和R7各自优选地或特别地具有上文已经指出的，与说明本发明式(I)化合物相关的，作为优选的或特别优选的R1，R2，R3，R4，R5和R7的定义。
式(Ia)是本发明新的化合物；其可以通过本发明方法(a)制备。
式(III)提供了在为了制备式(I)化合物的本发明方法(b)中也用作起始物的氨基化合物的通式定义。在式(III)中，R8优选地或特别地具有上文已经指出的，与说明本发明式(I)化合物相关的，作为优选的或特别优选的R8的定义。
式(III)起始材料是用于合成的已知化学品。
式(IVa)和(IVb)提供了为了制备通式(I)的化合物而在本发明方法(c)中也用作起始物的醇或硫醇的通式定义。在式(IVa)和(IVb)中，Q1，Q2，R9和R10各自优选地或特别地具有上文已经指出的，与说明本发明式(I)化合物相关的，作为优选的或特别优选的Q1，Q2，R9和R10的定义。
式(IVa)和(IVb)起始材料是用于合成的已知化学品。
进行本发明方法(a)至(c)的合适的稀释剂特别是惰性有机溶剂。特别包括脂肪族，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，二乙二醇单甲基醚，二乙二醇单乙基醚以及它们与水的混合物或纯水。
本发明方法(a)在反应助剂存在下进行，这里优选的反应助剂是具有还原作用的化合物，例如乙酸中的锌粉，钯存在下的氢，连二亚硫酸钠和二甲硫。
进行本发明方法(a)时，反应温度可以在相当宽的范围内变化。一般情况下，方法(a)在-100℃和+50℃之间的温度下进行，优选在-80℃和+30℃之间的温度下进行。
本发明方法(a)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在本发明方法(a)的优选实施方案中，首先将式(II)起始物加入到稀释剂中并冷却到所需温度，然后引入臭氧，直到反应终止。移去冷却浴，并计量加入反应助剂，并在需要的温度下搅拌混合物，直到反应终止。通过常规方法进行后处理(参见制备实施例)。
用于本发明方法(b)的合适的反应助剂一般是常规无机碱或有机碱或酸受体。它们优选包括碱土金属或碱金属乙酸盐，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，氨基锂，氨基钠，氨基钾或氨基钙，碳酸钠，碳酸钾或碳酸钙，碳酸氢钾，碳酸氢钠或碳酸氢钙，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，甲醇钠或甲醇钾，乙醇钠或乙醇钾，正-或异丙醇钠或正-或异丙醇钾，正-、异-、仲-或叔-丁醇钠或正-、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，三丁基胺，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-甲基-、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(b)时，反应温度可以在相当宽的范围内变化。一般情况下，方法(b)在0℃和150℃之间的温度下进行，优选10℃和120℃之间的温度。
本发明方法(b)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在实施本发明方法(b)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起始物组分。反应一般在合适的稀释剂中在反应助剂存在下进行，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)。
本发明方法(c)优选在反应助剂存在下进行，这里合适的反应助剂是氧化剂，例如过氧化氢，和酸例如硫酸。
进行本发明方法(c)时，反应温度可以在相当宽的范围内变化。一般情况下，方法(c)在0℃和120℃之间的温度下进行，优选在10℃和100℃之间的温度下进行。
本发明方法(c)一般在大气压下进行。但是也可以在加压或减压下进行本发明方法-一般在0.1至10巴之间。
在本发明方法(c)的优选实施方案中，向式(Ia)起始物和式(IVa)或(IVb)醇或硫醇的混合物中加入反应助剂，搅拌混合物，直到反应终止。通过常规方法进行后处理(参见制备实施例)。
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。本发明物质是作为总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)，甜菜属(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)，Cycnodon，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绝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防治杂草。这些化合物也被用来在多年生种植植物场所，草坪，运动场和牧场防治杂草，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防治杂草。
本发明式(I)化合物特别适用于通过芽前和芽后方法在单子叶和双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、和浸有活性化合物材料的天然和合成材料，以及包裹在聚合物中的细微胶囊。
这些型剂可以用已知的方式生产，例如，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。
用水作扩充剂的情况下，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，例如石油馏份，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，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。其它的添加剂可以是矿物油和植物油。
也可能使用着色剂，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，本发明活性化合物可以照原样使用或以其制剂形式，也可以作为与已知除草剂的混合物使用，可以是最终制剂或容器混合物。
适用于所述混合物的是已知的除草剂，例如N-酰苯胺类，例如吡氟草胺和敌稗；芳基羧酸类，例如二氯吡啶甲酸，麦草畏和毒莠定；芳基氧基链烷酸类，例如2，4-滴，2，4-滴丁酸，2，4-滴丙酸，氟草烟，2甲4氯，2甲4氯丙酸和绿草定；芳基氧基苯氧基链烷酸酯类，例如禾草灵，噁唑禾草灵，吡氟禾草灵，吡氟氯禾灵和喹禾灵；吖嗪酮类，例如杀草敏和哒草伏；氨基甲酸酯类，例如氯苯胺灵，甜菜安，甜菜宁和苯胺灵；氯代N-乙酰苯胺类，例如甲草胺，乙草安，丁草安，吡草安，异丙甲草胺，丙草安和毒草安；二硝基苯胺类，例如安磺灵，二甲戊乐灵和氟乐灵；二苯基醚类，例如三氟羧草醚，甲羧除草醚，乙羧氟草醚，氟磺胺草醚，halosafen，乳氟禾草灵和乙氧氟草醚；脲类，例如氯麦隆，敌草隆，伏草隆，异丙隆，利谷隆和甲基苯噻隆；羟胺类，例如禾草灭，烯草酮，噻草隆，稀禾定和肟草酮；咪唑啉酮类，例如咪草烟，咪草酯，灭草烟和灭草喹；腈类，例如溴苯腈，敌草腈和碘苯腈；氧乙酰胺类，例如苯噻草胺；磺酰脲类，例如amidosulfuron，苄嘧黄隆，氯嘧黄隆，氯黄隆，醚黄隆，甲黄隆，烟嘧黄隆，氟嘧黄隆，吡嘧黄隆，噻黄隆，醚苯黄隆和苯黄隆；硫代氨基甲酸酯类，例如克草猛，灭草特，燕麦畏，茵达灭，禾草畏，草达灭，苄草丹，杀草丹和野燕畏；三嗪类，例如莠去津，氰草津，西玛津，西草净，特丁净和terbutylazine；三嗪酮类，例如环嗪酮，苯嗪草酮和嗪草酮；其它类，例如氨基三唑，呋草黄，灭草松，环庚草醚，异噁草酮，二氯吡啶酸，双苯唑快，氟硫草定，乙呋草黄，氟咯草酮，草铵膦，草甘膦，isoxaben，哒草特，二氯喹啉酸，喹草酸，草硫磷和灭草环。
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照原样或以其制剂形式使用，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。其也可以在播种前直接掺合到土壤中。
使用的活性化合物的量可以在一个基本的范围内变化。这主要取决于期望的效果的性质。一般情况下，使用的量在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。
下面的实施例可以说明本发明活性化合物的制备和应用。制备实施例 实施例1 
(方法(a))向已经冷却到-70℃的8.7g(22mmol)1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和600ml二氯甲烷的混合物中通入臭氧45分钟。然后移去冷却浴，混合物与10ml二甲硫混合。一旦混合物温热至室温(大约20℃)，分离各相，有机相用水洗涤，硫酸钠干燥并过滤。用水泵抽真空来浓缩滤液，残余物溶解于乙醚，并且吸滤以分离结晶产物。
得到7.4g(理论量的99％)1-[4-氰基-2-氟-5-甲酰基-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177℃。实施例2 (方法(b))
室温下(大约20℃)，将1.0g(2.9mmol)1-[4-氰基-2-氟-5-甲酰基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶，0.25g(3.0mmol)O-甲基-羟胺盐酸盐，0.25g(3.0mmol)乙酸钠和20ml乙醇的混合物搅拌大约90分钟。然后用水泵抽真空来浓缩混合物，并且将残余物溶解于水，与2N盐酸混合，并用乙醚萃取。硫酸钠干燥有机相并过滤。然后用水泵抽真空小心从滤液中蒸馏出溶剂。
得到0.8g(理论量的74％)1-[4-氰基-2-氟-5-甲氧亚氨基甲基-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80℃。实施例3 
(方法(c))
大约10℃下，将0.28g过氧化氢(30％浓度)和0.59g浓硫酸混合，在大约20℃下搅拌大约2小时，然后加入到1.0g(2.9mmol)1-[4-氰基-2-氟-5-甲酰基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和20ml甲醇的混合物中，反应混合物在室温下(大约20℃)搅拌大约15小时，吸滤分离结晶产物。
得到0.70g(理论量的62％)1-[4-氰基-2-氟-5-二甲氧基甲基-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164℃。
通过制备实施例1-3的方法，并且根据关于本发明制备方法的一般性描述，也能够制备例如下面表1中列出的式(I)化合物。
表1：式(I)化合物的实施例
式(II)起始物： 实施例(II-1) 
将1.8g(21mmol)丙烯酸甲酯，1.6g(15.5mmol)亚硝酸叔丁酯，1.6g(12mmol)氯化铜(II)和50ml乙腈的混合物冷却到大约0℃，并且在该温度下向其中滴加20ml乙腈中的3.3g(10mmol)1-(5-氨基-4-氰基-2-氟-苯基)-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶的溶液。然后使反应混合物温热至室温，并且在该温度下搅拌18小时。接着，加入20ml1N盐酸后，用乙酸乙酯萃取混合物，并用硫酸钠干燥有机相和过滤。浓缩滤液，并且残余物通过柱色谱处理。得到2.8g(理论量的65％)1-[4-氰基-2-氟-5-(2-氯-2-甲氧羰基-乙基)-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46℃。
搅拌下向已经冷却到0℃的2.0g(4.6mmol)1-[4-氰基-2-氟-5-(2-氯-2-甲氧羰基-乙基)-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶和30mlN，N-二甲基甲酰胺的混合物中加入0.22g氢化钠(60％浓度)，反应混合物首先在0℃下搅拌15分钟，然后在20℃搅拌大约60分钟，并且最后在60℃搅拌6小时。然后水泵抽真空浓缩混合物，残余物与二异丙基醚搅拌，吸滤分离结晶产物。得到1.1g(理论量的60％)1-[4-氰基-2-氟-5-(2-甲氧羰基-乙烯基)-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154℃。式(V)起始物 实施例(V-1)
搅拌下向0.50g(1.2mmol)1-[4-氰基-2-氟-5-三氟乙酰基氨基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶，1ml三乙胺和50ml乙腈的混合物中加入0.17g(1.2mmol)新戊酰氯，反应混合物在20℃下搅拌18小时，再在60℃下搅拌15小时。然后水泵抽真空浓缩混合物，残余物用1N盐酸/乙酸乙酯振摇，分离有机相，硫酸钠干燥并过滤。水泵抽真空浓缩滤液，并且残余物通过柱色谱处理(硅胶，氯仿/乙酸乙酯，体积比1∶1)。
除了未反应的1-[4-氰基-2-氟-5-三氟乙酰基氨基-苯基]-3，6-二氢-2，6-二氧代-3-甲基-4-三氟甲基-1(2H)-嘧啶(第一级分：0.30g)，得到作为第二级分的0.2g(理论量的50％)1-[4-氰基-2-氟-5-氨基-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195℃。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
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，用活性化合物制剂对土壤喷雾。有益的是，每单位面积用的水的量保持不变。制剂中活性化合物的浓度并不重要，只有每单位面积施用的活性化合物的量是重要的。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。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30-125g/ha之间的比例施用时，例如制备实施例1，2和4的化合物显示出非常强的除杂草例如苋属(Amaranthus)(95％)，芥属(Sinapis)(100％)，苍耳属(Xanthium)(100％)，马唐属(Digitaria)(80-100％)，狗尾草属(Setaria)(95-100％)，藜属(Chenopodium)(100％)，母菊属(Matricaria)(100％)，和婆婆纳属(Veronica)(100％)的除草活性，并且农作物例如玉米，大麦和棉花对它们有好的耐受性(0-30％)。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具体期望量的活性化合物。选择喷雾液的浓度，使以1000L水/公顷施用具体期望量的活性化合物。
三星期后，以与未处理对照物生长相比较的杀伤百分率测定对植物的杀伤程度。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30-125g/ha之间的比例施用时，例如制备实施例1，2和4的化合物显示出非常强的除杂草例如苘麻属(Abutilon)(100％)，苋属(Amaranthus)(100％)，猪殃殃属(Galium)(100％)，曼陀罗属(Datura)(100％)，蓼属(Polygonum)(100％)和茄属(Solanum)(100％)的活性，并且农作物例如小麦对它们中的一些有好的耐受性(10％)。
Claims (6)
1.通式(I)取代的苯基尿嘧啶：特征在于R1代表氢，R2代表被氟取代的C1-4烷基，R3代表C1-6烷基，R4代表卤素，R5代表氰基，R6代表下面的基团之一：
其中Q1和Q2各自代表氧，R7在每种情况下代表氢，R8代表C1-6-烷氧基，二(C1-4-烷基)-氨基，R9和R10各自代表C1-4烷基。
2.权利要求1的通式(I)的取代的苯基尿嘧啶，特征在于，R2代表CF3，R3代表CH3，R4代表F，R8代表-OCH3，-N(CH3)2，R9和R10各自代表CH3。
3.权利要求1的通式(I)的取代的苯基尿嘧啶的制备方法，特征在于(a)通式(II)的链烯基苯基尿嘧啶
其中R1，R2，R3，R4，R5和R7各自如上定义，和R11和R12各自代表氢，氰基，羧基或者代表各自任选被取代的烷基或烷氧羰基，与臭氧反应，或者(b)通式(Ia)的羰基苯基尿嘧啶其中R1，R2，R3，R4，R5和R7各自如上定义，与通式(III)的氨基化合物反应，
H2N-R8 (III)其中R8如上定义，或者与式(III)化合物的酸加成物反应，或者(c)通式(Ia)的羰基苯基尿嘧啶
其中R1，R2，R3，R4，R5和R7各自如上定义，与通式(IVa)或(IVb)醇和/或硫醇反应，
HQ1R9 (IVa) HQ2R10 (IVb)其中Q1，Q2，R9和R10各自如上定义。
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。
5.防治不期望植物的方法，特征在于，使权利要求1的通式(I)的苯基尿嘧啶作用于不期望植物和/或其生长地域。
6.权利要求1的通式(I)的苯基尿嘧啶控制不期望植物的用途。
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| WO1993006090A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Aktiengesellschaft | Substituierte-3-phenylurazile als herbizide |
| DE4237920A1 (en) * | 1991-11-13 | 1993-05-19 | Ciba Geigy Ag | 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape |
| EP0542685A1 (de) * | 1991-11-13 | 1993-05-19 | Ciba-Geigy Ag | Neue 3-Aryluracil-Derivate und deren Verwendung zur Unkrautbekämpfung |
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| JP3089621B2 (ja) | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
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| KR100239201B1 (ko) | 1991-09-23 | 2000-02-01 | 로버트 엠 존슨 | 10-데스아세톡시탁솔 유도체 |
| US5681794A (en) | 1993-08-18 | 1997-10-28 | Bayer Aktiengesellschaft | N-cyanoaryl-nitrogen heterocycles |
| ES2110667T3 (es) | 1993-08-18 | 1998-02-16 | Bayer Ag | N-cianoaril-heterociclos nitrogenados. |
| DE4329537A1 (de) | 1993-09-02 | 1995-03-09 | Basf Ag | Substituierte 1-Amino-3-phenyluracile |
| DE19621311A1 (de) | 1996-05-28 | 1997-12-04 | Bayer Ag | Substituierte Phenyluracile |
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| WO1993006090A1 (de) * | 1991-09-20 | 1993-04-01 | Basf Aktiengesellschaft | Substituierte-3-phenylurazile als herbizide |
| DE4237920A1 (en) * | 1991-11-13 | 1993-05-19 | Ciba Geigy Ag | 3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape |
| EP0542685A1 (de) * | 1991-11-13 | 1993-05-19 | Ciba-Geigy Ag | Neue 3-Aryluracil-Derivate und deren Verwendung zur Unkrautbekämpfung |
| WO1995025725A1 (en) * | 1994-03-21 | 1995-09-28 | Uniroyal Chemical Company, Inc. | Pyrimidinyl aryl ketone oximes |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000510855A (ja) | 2000-08-22 |
| US6245714B1 (en) | 2001-06-12 |
| US6437126B1 (en) | 2002-08-20 |
| DE19621311A1 (de) | 1997-12-04 |
| DE59712222D1 (de) | 2005-04-14 |
| EP0906291A1 (de) | 1999-04-07 |
| WO1997045418A1 (de) | 1997-12-04 |
| CN1220663A (zh) | 1999-06-23 |
| CA2256415C (en) | 2006-10-31 |
| EP0906291B1 (de) | 2005-03-09 |
| IL126973A0 (en) | 1999-09-22 |
| AU716994B2 (en) | 2000-03-16 |
| ES2238721T3 (es) | 2005-09-01 |
| CA2256415A1 (en) | 1997-12-04 |
| AU2955597A (en) | 1998-01-05 |
| IL126973A (en) | 2003-02-12 |
| BR9709466A (pt) | 1999-08-10 |
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