CN102762552B - 作为除草剂的3-(3,4-二氢-2h-苯并[1,4]*嗪-6-基)-1h-嘧啶-2,4-二酮化合物 - Google Patents
作为除草剂的3-(3,4-二氢-2h-苯并[1,4]*嗪-6-基)-1h-嘧啶-2,4-二酮化合物 Download PDFInfo
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- CN102762552B CN102762552B CN201080061379.7A CN201080061379A CN102762552B CN 102762552 B CN102762552 B CN 102762552B CN 201080061379 A CN201080061379 A CN 201080061379A CN 102762552 B CN102762552 B CN 102762552B
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
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- 229910052731 fluorine Inorganic materials 0.000 claims description 37
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- 125000003118 aryl group Chemical group 0.000 claims description 5
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- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 5
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- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
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- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
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- UJMBCXLDXJUMFB-GLCFPVLVSA-K tartrazine Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-GLCFPVLVSA-K 0.000 description 1
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- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
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- 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
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- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
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- BFGQTWYXWNCTSX-UHFFFAOYSA-N triazine-4,5-dione Chemical class O=C1C=NN=NC1=O BFGQTWYXWNCTSX-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- 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
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及式(I)的尿嘧啶,其中各变量根据说明书定义,制备式(I)的尿嘧啶的方法和中间体,包含它们的组合物及其作为除草剂,即防治有害植物的用途,还涉及一种防治不希望的植物生长的方法,该方法包括使除草有效量的至少一种式(I)的尿嘧啶作用于植物、其种子和/或其生长地上。
Description
本发明涉及如下所定义的通式I的尿嘧啶及其作为除草剂的用途。此外,本发明涉及作物保护组合物以及一种防止不希望的植物生长的方法。
例如,WO90/15057尤其描述了具有除草作用的结构类似化合物,其与本发明尿嘧啶I的不同在于苯并[1,4]嗪环优选在2位未被取代或者带有烷基,而本发明式I的尿嘧啶在所述位置被至少一个卤原子取代。
然而,这些已知化合物对于有害植物的除草性能并不总是完全令人满意。
因此,本发明的目的是提供具有改进除草作用的尿嘧啶类。尤其要提供具有高除草活性,尤其甚至在低施用率下也具有高除草活性并且与商业利用的农作物充分相容的尿嘧啶类。
这些和其他目的由如下所定义的式I的尿嘧啶及其可农用盐实现。
因此,本发明提供了式I的尿嘧啶:
其中
R1为氢或卤素;
R2为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基、C3-C6卤代炔基、C1-C6烷氧基或C3-C6环烷基-C1-C6烷基;
R3为氢或卤素;
R4为卤素;
R5为氢、NH2、C1-C6烷基或C3-C6炔基;
R6为氢、C1-C6烷基或C1-C6卤代烷基;
R7为氢或C1-C6烷基;
X为O或S;和
Y为O或S;
包括其可农用盐。
本发明还提供了除草活性化合物,其包含至少一种式I的尿嘧啶和至少一种选自除草活性化合物B和安全剂C的其他化合物。
本发明还提供了通式I的尿嘧啶作为除草剂,即防治不希望的植物的用途。
本发明还提供了包含至少一种式I的尿嘧啶和常用于配制作物保护剂的助剂的混合物。
此外,本发明提供了一种防治不希望的植物生长的方法,其中使除草有效量的至少一种式I的尿嘧啶作用于植物、其种子和/或其生长地。施用可以不希望的植物出苗之前、之中和/或之后进行。
此外,本发明涉及制备式I的尿嘧啶的方法和中间体。
本发明的其他实施方案由权利要求书、说明书和实施例明了。应理解的是本发明主题的上述特征和下文仍要说明的那些不仅可以用于在各种特定情形下所给组合,而且可以在不背离本发明范围下用于其他组合。
本文所用术语“防治”和“防除”是同义词。
本文所用术语“不希望的植物生长”和“有害植物”是同义词。
若本文所述式I的尿嘧啶能够形成几何异构体,例如E/Z异构体,则可以在本发明组合物中使用纯异构体及其混合物二者。
若本文所述式I的尿嘧啶具有一个或多个手性中心且因此以对映体或非对映体存在,则可以在本发明组合物中使用纯对映体和非对映体二者。
若本文所述式I的尿嘧啶具有可以被离子化的官能基团,则它们还可以以其可农用盐或其混合物形式使用。
合适的通常是其阳离子对活性化合物的作用没有不利影响(“可农用”)的那些阳离子的盐。优选的阳离子是碱金属的离子,优选锂、钠和钾离子,碱土金属的离子,优选钙和镁离子,以及过渡金属的离子,优选锰、铜、锌和铁离子,此外还有铵和其中1-4个氢原子被C1-C4烷基、羟基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的取代铵(下文也称为有机铵),优选铵、甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四乙基铵、四丁基铵、2-羟基乙基铵、2-(2-羟基乙氧基)乙-1-基铵、二(2-羟基乙-1-基)铵、苄基三甲基铵、苄基三乙基铵,此外还有离子,锍离子,优选三(C1-C4烷基)锍,如三甲基锍,以及氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、碘离子、硫酸氢根、甲基硫酸根、硫酸根、磷酸二氢根、磷酸氢根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。
在本文所述变量的定义中,尤其就R1-R7所提到的有机结构部分象术语卤素一样为各基团成员的单独列举的集合性术语。术语卤素在每种情况下表示氟、氯、溴或碘。所有烃链,即所有烷基,可以是直链或支化的,前缀Cn-Cm在每种情况下表示该基团中的可能碳原子数目。
该类含义的实例为:
-C1-C4烷基以及还有C3-C6环烷基-C1-C4烷基的C1-C4烷基结构部分:例如CH3、C2H5、正丙基和CH(CH3)2、正丁基、CH(CH3)-C2H5、CH2-CH(CH3)2和C(CH3)3;
-C1-C6烷基以及还有C1-C6烷氧基-C1-C6烷基的C1-C6烷基结构部分:如上所述的C1-C4烷基以及还有例如正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基或1-乙基-2-甲基丙基,优选甲基、乙基、正丙基、1-甲基乙基、正丁基、1,1-二甲基乙基、正戊基或正己基;-C1-C4卤代烷基:部分或完全被氟、氯、溴和/或碘取代的如上所述的C1-C4烷基,例如氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯一氟甲基、一氯二氟甲基、溴甲基、碘甲基、2-氟乙基、2-氯乙基、2-溴乙基、2-碘乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基、2-氟丙基、3-氟丙基、2,2-二氟丙基、2,3-二氟丙基、2-氯丙基、3-氯丙基、2,3-二氯丙基、2-溴丙基、3-溴丙基、3,3,3-三氟丙基、3,3,3-三氯丙基、2,2,3,3,3-五氟丙基、七氟丙基、1-氟甲基-2-氟乙基、1-氯甲基-2-氯乙基、1-溴甲基-2-溴乙基、4-氟丁基、4-氯丁基、4-溴丁基、九氟丁基、1,1,2,2-四氟乙基和1-三氟甲基-1,2,2,2-四氟乙基;
-C1-C6卤代烷基:如上所述的C1-C4卤代烷基以及例如还有5-氟戊基、5-氯戊基、5-溴戊基、5-碘戊基、十一氟戊基、6-氟己基、6-氯己基、6-溴己基、6-碘己基和十三氟己基;
-C3-C6环烷基以及还有C3-C6环烷基-C1-C6烷基、C3-C6环烷氧基的环烷基结构部分:具有3-6个环成员的单环饱和烃,如环丙基、环丁基、环戊基和环己基;
-C3-C6链烯基:例如1-丙烯基、2-丙烯基、1-甲基乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基;
-C2-C6链烯基和C2-C6链烯氧基、C2-C6卤代链烯氧基的链烯基结构部分:如上所述的C3-C6链烯基以及还有乙烯基;
-C3-C6卤代链烯基:部分或全部被氟、氯、溴和/或碘取代的如上所述的C3-C6链烯基,例如2-氯丙-2-烯-1-基、3-氯丙-2-烯-1-基、2,3-二氯丙-2-烯-1-基、3,3-二氯丙-2-烯-1-基、2,3,3-三氯-2-烯-1-基、2,3-二氯丁-2-烯-1-基、2-溴丙-2-烯-1-基、3-溴丙-2-烯-1-基、2,3-二溴丙-2-烯-1-基、3,3-二溴丙-2-烯-1-基、2,3,3-三溴-2-烯-1-基或2,3-二溴丁-2-烯-1-基;
-C3-C6炔基以及还有C3-C6炔氧基的C3-C6炔基结构部分:例如1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、1-戊炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-2-丁炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、3-甲基-1-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-1-戊炔基、3-甲基-4-戊炔基、4-甲基-1-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-2-丁炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-乙基-2-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基和1-乙基-1-甲基-2-丙炔基;
-C3-C6卤代炔基以及还有C3-C6卤代炔氧基的C3-C6卤代炔基结构部分:部分或全部被氟、氯、溴和/或碘取代的如上所述的C3-C6炔基,例如1,1-二氟丙-2-炔-1-基、3-氯丙-2-炔-1-基、3-溴丙-2-炔-1-基、3-碘丙-2-炔-1-基、4-氟丁-2-炔-1-基、4-氯丁-2-炔-1-基、1,1-二氟丁-2-炔-1-基、4-碘丁-3-炔-1-基、5-氟戊-3-炔-1-基、5-碘戊-4-炔-1-基、6-氟己-4-炔-1-基或6-碘己-5-炔-1-基;
-C1-C4烷氧基以及还有C1-C4烷氧基-C2-C4烷氧基、C1-C4烷硫基-C2-C4烷氧基的C1-C4烷氧基结构部分:例如甲氧基、乙氧基、丙氧基、1-甲基乙氧基、丁氧基、1-甲基丙氧基、2-甲基丙氧基和1,1-二甲基乙氧基;
-C1-C6烷氧基以及还有C1-C6卤代烷氧基、C1-C6氰基烷氧基的C1-C6烷氧基结构部分:如上所述的C1-C4烷氧基以及还有例如戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲氧基丁氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、2,2-二甲基丙氧基、1-乙基丙氧基、己氧基、1-甲基戊氧基、2-甲基戊氧基、3-甲基戊氧基、4-甲基戊氧基、1,1-二甲基丁氧基、1,2-二甲基丁氧基、1,3-二甲基丁氧基、2,2-二甲基丁氧基、2,3-二甲基丁氧基、3,3-二甲基丁氧基、1-乙基丁氧基、2-乙基丁氧基、1,1,2-三甲基丙氧基、1,2,2-三甲基丙氧基、1-乙基-1-甲基丙氧基和1-乙基-2-甲基丙氧基;
-C1-C4烷硫基以及还有C1-C4烷硫基-C2-C4烷氧基的C1-C4烷硫基结构部分:例如甲硫基、乙硫基、丙硫基、1-甲基乙硫基、丁硫基、1-甲基丙硫基、2-甲基丙硫基和1,1-二甲基乙硫基;
-C1-C6烷硫基:如上所述的C1-C4烷硫基以及还有例如戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、2,2-二甲基丙硫基、1-乙基丙硫基、己硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、1-甲基戊硫基、2-甲基戊硫基、3-甲基戊硫基、4-甲基戊硫基、1,1-二甲基丁硫基、1,2-二甲基丁硫基、1,3-二甲基丁硫基、2,2-二甲基丁硫基、2,3-二甲基丁硫基、3,3-二甲基丁硫基、1-乙基丁硫基、2-乙基丁硫基、1,1,2-三甲基丙硫基、1,2,2-三甲基丙硫基、1-乙基-1-甲基丙硫基和1-乙基-2-甲基丙硫基;
-芳基以及还有芳氧基的芳基结构部分:具有6-14个环成员的单至三核芳族碳环,如苯基、萘基、蒽基和菲基。
本文在下文中提到的本发明优选实施方案必须相互独立地或者相互组合地理解为优选的。
根据本发明的优选实施方案,还优选如下那些式I的尿嘧啶,其中各变量相互独立地或者相互组合地具有下列含义:
R1为氢;
还优选为卤素,特别优选F或Cl,尤其优选F;
R2为C3-C6炔基或C3-C6卤代炔基,优选C3炔基或C3卤代炔基,特别优选CH2C≡CH、CH2C≡CCl或CH2C≡CBr;
还优选为C3-C6炔基或C3-C6环烷基-C1-C6烷基,特别优选炔丙基或环丙基甲基;
还优选为C3-C6炔基,优选C3炔基,特别优选CH2C≡CH;
还优选为C3-C6卤代炔基,优选C3卤代炔基,特别优选CH2C≡CCl或CH2C≡CBr;
R3为氢;
还优选为卤素,特别优选F;
还优选为氢或F;
R4为F;
R5为氢、NH2或C1-C6烷基,优选NH2或C1-C4烷基,特别优选NH2或CH3;
还优选为C1-C6烷基,优选C1-C4烷基,特别优选CH3;
R6为C1-C6烷基或C1-C6卤代烷基,优选C1-C4烷基或C1-C4卤代烷基,更优选C1-C4卤代烷基,特别优选C1-C2卤代烷基,尤其优选CF3;
R7为氢;
还优选为C1-C6烷基,优选C1-C4烷基,特别优选CH3;
X为O,
还优选为S;
Y为O,
还优选为S。
特别优选其中R4为F,R5为CH3,R6为CF3,R7为氢,X为O且Y为O的式I的尿嘧啶,其在本文中在下文也称为式Ia的尿嘧啶:
其中变量R1、R2和R3具有如上所定义的含义,尤其是优选含义。
特别优选表A的式Ia1-Ia60的尿嘧啶,其中变量R1、R2和R3的定义不仅相互组合而且在每种情况下也独立地对本发明化合物特别重要:
表
还优选式Ib的尿嘧啶,特别优选式Ib1-Ib60的尿嘧啶,其与对应的式Ia1-Ia60的尿嘧啶的不同仅在于R5为NH2:
还优选式Ic的尿嘧啶,特别优选式Ic1-Ic60的尿嘧啶,其与对应的式Ia1-Ia60的尿嘧啶的不同仅在于R5为氢:
本发明式I的尿嘧啶可以通过有机化学的标准方法制备,例如通过使式II的异(硫)氰酸酯与式III的烯胺反应:
变量R1-R7、X和Y各自如上所定义,优选如上面所优选定义。
在式II的异氰酸酯与式III的烯胺的该反应的优选实施方案中,R5优选为氢、C1-C6烷基或C3-C6炔基,更优选氢或C1-C6烷基,最优选氢。
L1为可亲核置换的离去基团;优选C1-C6烷氧基、C1-C6卤代烷氧基、C1-C4烷氧基-C2-C4烷氧基、C1-C4烷硫基-C2C4烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C3-C6炔氧基、C3-C6卤代炔氧基、C3-C6环烷氧基、C1-C6氰基烷氧基或苄氧基,其本身可以在苯基环上部分或完全被卤代和/或可以被1-3个选自如下的基团取代:氰基、硝基、C1-C4烷基、C1-C4烷氧基和C1-C4烷硫基;更优选C1-C6烷氧基、C1-C6卤代烷氧基、C1-C4烷氧基-C2-C4烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C3-C6炔氧基或C3-C6卤代炔氧基;非常优选C1-C6烷氧基、C1-C4烷氧基-C2-C4烷氧基、C2-C6链烯氧基或C3-C6炔氧基;特别优选C1-C6烷氧基。
式II的异(硫)氰酸酯与式III的烯胺的该反应通常在例如-20℃至80℃下在惰性有机溶剂中在碱存在下进行(例如WO05/054208).
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、氯仿和氯苯,醚类如***、二异丙醚、叔丁基甲基醚、二烷、二甘醇二甲基醚、茴香醚和四氢呋喃,腈类如乙腈和丙腈,醇类如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,羧酸酯类如乙酸丁酯,以及还有二甲亚砜、二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮;更优选二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮。
还可以使用所述溶剂的混合物。
有用的碱通常为无机化合物,如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属氨化物,如氨基锂、氨基钠和氨基钾,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钠、碳酸钾、碳酸钙和碳酸铯,以及还有碱金属碳酸氢盐,如碳酸氢钠,有机金属化合物,尤其是碱金属烷基化物,如甲基锂、丁基锂和苯基锂,碱金属和碱土金属醇盐,如甲醇锂、甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶和4-二甲氨基吡啶以及还有双环胺。特别优选碱金属和碱土金属氢氧化物、碱金属和碱土金属碳酸盐以及还有碱金属和碱土金属醇盐。
碱通常基于式II的异氰酸酯以过量使用,并且它们还可以用作溶剂。可能有利的是在一定时间内分开加入该碱。
反应混合物以常规方式后处理,例如与水混合,分离各相以及合适的话层析提纯粗产物。某些中间体和终产物以粘稠油形式得到,通常可以将它们在减压和温和升高的温度下提纯或除去挥发性组分。若中间体和终产物以固体得到,则还可以通过重结晶或浸煮进行提纯。
式II的异(硫)氰酸酯又可以由对应的胺化合物IV得到:
合适的(硫)光气化剂光气、双光气或三光气以及各自的相应硫代衍生物中,其中优选双光气。
胺IV的反应通常在-20℃至反应混合物的沸点,优选10-200℃,特别优选20-150℃下在惰性有机溶剂中以及合适的话在碱存在下进行(例如WO04/39768)。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如***、二异丙醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,乙二醇醚,如乙二醇二甲基醚、乙二醇二乙基醚、二甘醇二甲基醚,酯类,如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类,如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,以及二甲亚砜。特别优选芳族烃类,如甲苯、邻二甲苯、间二甲苯和对二甲苯。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属碳酸盐如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐如碳酸氢钠,此外还有有机碱如叔胺,如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶,以及还有双环胺。特别优选叔胺如三乙胺。
碱通常以催化量使用,然而它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
也为制备式I的尿嘧啶所要求的式III的烯胺公开于文献中(例如A.Lutz,A.和S.Trotto,J.ofHeterocyclicChem.1972,9,3,513-522)并且可以相应制备。
本发明式I的尿嘧啶还可以通过使式V的(硫代)氨基甲酸酯与式III的烯胺反应而制备:
变量R1-R7、X、Y和L1各自如上所定义,优选如上面所优选定义。L2为可亲核置换的离去基团,优选C1-C6烷氧基、C1-C6烷硫基或芳氧基,其中芳基结构部分本身可以部分或完全被卤代和/或可以被1-3个选自如下的基团取代:氰基、硝基、C1-C4烷基、C1-C4烷氧基和C1-C4烷硫基;特别优选C1-C6烷氧基、C1-C6烷硫基或苯氧基,其中苯基结构部分本身可以部分或完全被卤代和/或可以被1-3个选自如下的基团取代:氰基、硝基、C1-C4烷基、C1-C4烷氧基和C1-C4烷硫基;更优选C1-C6烷氧基、C1-C6烷硫基和苯氧基;最优选C1-C6烷氧基。
式V的(硫代)氨基甲酸酯与式III的烯胺的该反应通常在室温以上的温度,例如25-200℃,优选90-190℃,更优选100-140℃下在惰性有机溶剂中在碱存在下进行(例如WO99/31091)。
合适的溶剂和碱是上面就式II的异氰酸酯与式III的烯胺反应所提到的那些。
制备式I的尿嘧啶所要求的式V的(硫代)氨基甲酸酯可以类似于已知方法通过使式IV的胺与式X化合物反应而制备(例如Houben-Weyl,MethodenderorganischenChemie[有机化学方法],E5,1985,第972-980页以及还有VIII,第655页和XI第2部分,第10页):
其中R1-R4、X、Y和L2各自如上所定义且L3为可亲核置换的离去基团。
式V的(硫代)氨基甲酸酯是新化合物且如上所示为制备本发明式I的尿嘧啶的合适中间体。
因此,本发明还涉及式V的(硫代)氨基甲酸酯:
其中
R1为氢或卤素;
R2为氢、C1-C6烷基、C1-C6卤代烷基、C3-C6环烷基、C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基、C3-C6卤代炔基、C1-C6烷氧基或C3-C6环烷基-C1-C6烷基;
R3为氢或卤素;
R4为氢;
X为O或S;
Y为O或S;和
L2为可亲核置换的离去基团,优选C1-C6烷氧基或C1-C6烷硫基,更优选C1-C6烷氧基。
对于各变量,中间体式V的(硫代)氨基甲酸酯的特别优选实施方案相互独立地或相互结合地对应于式I的尿嘧啶的变量R1、R2、R3、R4、X和Y的那些。
制备式V的(硫代)氨基甲酸酯所要求的式X化合物公开于文献中(例如Houben-Weyl,MethodenderorganischenChemie,E4,1983,第6-17页)并且可以相应地制备或者可以市购。
其中R5为NH2、C1-C6烷基或C3-C6炔基的那些式I的尿嘧啶还可以通过将其中R5为H的式I的那些尿嘧啶胺化或烷基化而制备:
胺化或烷基化可以类似于已知方法进行(例如WO05/054208;WO06/125746)。
制备式V的(硫代)氨基甲酸酯所要求的氨基化合物IV可以由对应的硝基化合物VI得到:
优选氨基化合物IVa(=其中R4为氟且X为O的氨基化合物IV):
硝基化合物VI的还原通常在20C至反应混合物的沸点,优选20-200℃,特别优选20-100℃下在惰性有机溶剂中进行[Organikum,HeideIberg,1993,第320-323页]。
合适的还原剂是新生H2;在催化量的过渡金属或过渡金属化合物,尤其是第8过渡族的那些,优选Ni、Pd、Pt、Ru或Rh(直接使用,以负载形式如经由活性炭、Al、ZrO2、TiO2、SiO2、碳酸盐等负载或以化合物如氧化钯或氧化铂)存在下的氢气;或金属氢化物、半金属氢化物如氢化铝和由其衍生的氢化物如氢化铝锂、二异丁基氢化铝,硼氢化物如乙硼烷或由其衍生的硼烷化物(boranate)如硼氢化钠或硼氢化锂。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,乙二醇醚,如乙二醇二甲基醚、乙二醇二乙基醚、二甘醇二甲基醚,酯类,如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类,如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类,如乙腈和丙腈,醇类,如甲醇、乙醇、正丙醇、异丙醇、正丁醇和叔丁醇,特别优选甲苯和甲醇。
还可以使用所述溶剂的混合物。
后处理可以以已知方式进行。
硝基化合物VI又可以由相应的苯基化合物VII得到:
苯基化合物VII的硝化通常在-20℃至100℃,特别优选0-20℃下进行[Organikum,Heidelberg,1993,第553-557页]。
合适的硝化剂是浓H2SO4和浓HNO3的混合物,混合比优选为50∶1-1∶50,更优选20∶1-1∶20,尤其优选10∶1-1∶10。
后处理可以以已知方式进行。
还可以通过将其中R2为H的硝基化合物VI烷基化而制备其中R2为C3-C6链烯基、C3-C6卤代链烯基、C3-C6炔基或C3-C6卤代炔基,优选C3-C6炔基的那些硝基化合物VI:
该反应通常在-78℃至反应混合物的沸点,优选-40℃至100℃,特别优选-20℃至30℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
合适的溶剂为脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,乙二醇醚,如乙二醇二甲基醚、乙二醇二乙基醚、二甘醇二甲基醚,酯类,如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类,如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类,如乙腈和丙腈,酮类,如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,以及二甲亚砜。特别优选醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃。还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。特别优选叔胺,如三甲胺、三乙胺、二异丙基乙基胺以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾。
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
苯基化合物VII又可以由相应的乙酰胺VIII得到:
乙酰胺VIII的环化通常在0℃至反应混合物的沸点,优选0-140℃,特别优选20-120℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
L4为选自Cl、Br、I的卤素;优选Cl或Br;最优选Cl,还最优选Br。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,乙二醇醚,如乙二醇二甲基醚、乙二醇二乙基醚、二甘醇二甲基醚,酯类,如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类,如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类,如乙腈和丙腈,以及二甲亚砜。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢氧化物,如氢氧化锂、氢氧化钠、氢氧化钾和氢氧化钙,碱金属和碱土金属氧化物,如氧化锂、氧化钠、氧化钙和氧化镁,碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,金属有机化合物,优选碱金属烷基化物,如甲基锂、丁基锂和苯基锂,烷基卤化镁,如甲基氯化镁,以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。特别优选1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)。
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
乙酰胺VIII又可以由对应的苯酚IX得到:
该反应通常在-78℃至反应混合物的沸点,优选-40℃至100℃,特别优选-20℃至30℃下在惰性有机溶剂中在碱存在下进行[WO02/066471]。
L4为选自Cl、Br、I的卤素,优选Cl或Br,最优选Cl,还最优选Br。
L5是用于酰化的已知活化基团,例如卤素或C1-C6烷氧基,优选Cl或C1-C6烷氧基,最优选Cl、OCH3或OC2H5。
合适的溶剂是脂族烃类如戊烷、己烷、环己烷和C5-C8链烷烃的混合物,芳族烃类如甲苯、邻二甲苯、间二甲苯和对二甲苯,卤代烃类如二氯甲烷、1,2-二氯乙烷、氯仿和氯苯,醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃,乙二醇醚,如乙二醇二甲基醚、乙二醇二乙基醚、二甘醇二甲基醚,酯类,如乙酸乙酯、乙酸丙酯、异丁酸甲酯、乙酸异丁酯,羧酰胺类,如N,N-二甲基甲酰胺、N-甲基吡咯烷酮、N,N-二甲基乙酰胺,腈类,如乙腈和丙腈,酮类如丙酮、甲基乙基酮、二乙基酮和叔丁基甲基酮,以及二甲亚砜。
特别优选醚类如***、二异丙基醚、叔丁基甲基醚、二烷、茴香醚和四氢呋喃。
还可以使用所述溶剂的混合物。
合适的碱通常为无机化合物,如碱金属和碱土金属氢化物,如氢化锂、氢化钠、氢化钾和氢化钙,碱金属和碱土金属碳酸盐,如碳酸锂、碳酸钾和碳酸钙,以及碱金属碳酸氢盐,如碳酸氢钠,碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾、叔丁醇钾、叔戊醇钾和二甲氧基镁,此外还有有机碱,如叔胺如三甲胺、三乙胺、二异丙基乙基胺和N-甲基哌啶,吡啶,取代吡啶如可力丁、卢剔啶、N-甲基吗啉和4-二甲氨基吡啶以及还有双环胺。
特别优选叔胺如三甲胺、三乙胺、二异丙基乙基胺以及碱金属和碱土金属醇盐,如甲醇钠、乙醇钠、乙醇钾,
碱通常以催化量使用;然而,它们还可以以等摩尔量、过量使用或者合适的话可以用作溶剂。
后处理可以以已知方式进行。
制备乙酰胺VIII所需的苯酚IX由文献[WO02/066471]已知或者它们可以按照所引用文献制备和/或可市购。
制备乙酰胺VIII所需的化合物X可以市购。
对于制备式I化合物所提到的原料,就原料所提到的变量具有相同含义,优选在本文中就式I中的相应变量所提到的优选含义。
式I的尿嘧啶适合作为除草剂。它们适合直接使用或适合以适当配制的组合物(除草组合物)使用。本申请中所用术语“配制的组合物”和“除草组合物”为同义词。包含式I的尿嘧啶的除草组合物非常有效地防治非作物区域的植物生长,尤其是在高施用率下。它们在诸如小麦、稻、玉米、大豆和棉花的作物中作用于阔叶杂草和禾本科杂草而不对农作物造成任何显著的损害。该效果主要在低施用率下观察到。
取决于所述施用方法,式I的尿嘧啶或包含它们的组合物可以额外用于许多其他农作物以消除不希望的植物。合适的作物实例如下:洋葱(Alliumcepa)、凤梨(Ananascomosus)、落花生(Arachishypogaea)、石刁柏(Asparagusofficinalis)、燕麦(Avenasativa)、甜菜(Betavulgarisspec.altissima)、甜菜(Betavulgarisspec.rapa)、欧洲油菜(Brassicanapusvar.napus)、芜青甘蓝(Brassicanapusvar.napobrassica)、芜青(Brassicarapavar.silvestris)、羽衣甘蓝(Brassicaoleracea)、黑芥(Brassicanigra)、大叶茶(Camelliasinensis)、红花(Carthamustinctorius)、美国山核桃(Caryaillinoinensis)、柠檬(Citruslimon)、甜橙(Citrussinensis)、小果咖啡(Coffeaarabica)(中果咖啡(Coffeacanephora)、大果咖啡(Coffealiberica))、黄瓜(Cucumissativus)、狗牙根(Cynodondactylon)、胡萝卜(Daucuscarota)、油棕(Elaeisguineensis)、欧洲草莓(Fragariavesca)、大豆(Glycinemax)、陆地棉(Gossypiumhirsutum)(树棉(Gossypiumarboreum)、草棉(Gossypiumherbaceum)、Gossypiumvitifolium)、向日葵(Helianthusannuus)、Heveabrasiliensis、大麦(Hordeumvulgare)、啤酒花(Humuluslupulus)、甘薯(Ipomoeabatatas)、核桃(Juglansregia)、兵豆(Lensculinaris)、亚麻(Linumusitatissimum)、番茄(Lycopersiconlycopersicum)、苹果属(Malusspec.)、木薯(Manihotesculenta)、紫苜蓿(Medicagosativa)、芭蕉属(Musaspec.)、烟草(Nicotianatabacum)(黄花烟草(N.rustica))、油橄榄(Oleaeuropaea)、稻(Oryzasativa)、金甲豆(Phaseoluslunatus)、菜豆(Phaseolusvulgaris)、欧洲云杉(Piceaabies)、松属(Pinusspec.)、开心果(Pistaciavera)、Pisumsativum、欧洲甜樱桃(Prunusavium)、Prunuspersica、西洋梨(Pyruscommunis)、杏(Prunusarmeniaca)、欧洲酸樱桃(Prunuscerasus)、扁桃(Prunusdulcis)和欧洲李(Prunusdomestica)、Ribessylvestre、蓖麻(Ricinuscommunis)、甘蔗(Saccharumofficinarum)、黑麦(Secalecereale)、白芥(Sinapisalba)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghumbicolor)(高粱(S.vulgare))、可可树(Theobromacacao)、红车轴草(Trifoliumpratense)、普通小麦(Triticumaestivum)、小黑麦(Triticale)、硬粒小麦(Triticumdurum)、蚕豆(Viciafaba)、葡萄(Vitisvinifera)和玉蜀黍(Zeamays)。
优选的作物如下:落花生(Arachishypogaea)、甜菜(Betavulgarisspec.altissima)、欧洲油菜(Brassicanapusvar.napus)、羽衣甘蓝(Brassicaoleracea)、柠檬(Citruslimon)、甜橙(Citrussinensis)、小果咖啡(Coffeaarabica)(中果咖啡(Coffeacanephora)、大果咖啡(Coffealiberica))、狗牙根(Cynodondactylon)、大豆(Glycinemax)、陆地棉(Gossypiumhirsutum)(树棉(Gossypiumarboreum)、草棉(Gossypiumherbaceum)、Gossypiumvitifolium)、向日葵(Helianthusannuus)、大麦(Hordeumvulgare)、核桃(Juglansregia)、兵豆(Lensculinaris)、亚麻(Linumusitatissimum)、番茄(Lycopersiconlycopersicum)、苹果属(Malusspec.)、紫苜蓿(Medicagosativa)、烟草(Nicotianatabacum)(黄花烟草(N.rustica))、油橄榄(Oleaeuropaea)、稻(Oryzasativa)、金甲豆(Phaseoluslunatus)、菜豆(Phaseolusvulgaris)、开心果(Pistaciavera)、Pisumsativum、扁桃(Prunusdulcis)、甘蔗(Saccharumofficinarum)、黑麦(Secalecereale)、马铃薯(Solanumtuberosum)、两色蜀黍(Sorghumbicolor)(高粱(S.vulgare))、小黑麦(Triticale)、普通小麦(Triticumaestivum)、硬粒小麦(Triticumdurum)、蚕豆(Viciafaba)、葡萄(Vitisvinifera)和玉蜀黍(Zeamays)。
本发明式I的尿嘧啶还可以用于基因修饰植物。术语“基因修饰植物”应理解为其基因材料已经通过使用重组DNA技术以在自然情况下不易通过杂交、突变或自然重组得到的方式修饰的植物。通常将一个或多个基因整合到基因修饰植物的基因材料中以改善植物的某些性能。这类基因修饰还包括但不限于蛋白质、寡肽或多肽的靶向翻译后修饰,例如通过糖基化或聚合物加成如异戊二烯化、乙酰化或法呢基化结构部分或PEG结构部分。通过育种、诱变或基因工程修饰的植物例如因常规育种或基因工程方法而耐受特殊类别除草剂的施用,这些除草剂如羟基苯基丙酮酸二加氧酶(HPPD)抑制剂,乙酰乳酸合成酶(ALS)抑制剂,例如磺酰脲类(例如参见US6,222,100,WO01/82685,WO00/026390,WO97/41218,WO98/002526,WO98/02527,WO04/106529,WO05/20673,WO03/14357,WO03/13225,WO03/14356,WO04/16073)或咪唑啉酮类(例如参见US6,222,100,WO01/82685,WO00/26390,WO97/41218,WO98/02526,WO98/02527,WO04/106529,WO05/20673,WO03/014357,WO03/13225,WO03/14356,WO04/16073),烯醇丙酮酰莽草酸3-磷酸合成酶(EPSPS)抑制剂,例如草甘膦(glyphosate)(例如参见WO92/00377),谷氨酰胺合成酶(GS)抑制剂,例如草铵膦(glufosinate)(例如参见EP-A242236,EP-A242246)或苯腈类(oxynil)除草剂(例如参见US5,559,024)。几种栽培植物已经通过常规育种(诱变)方法而耐受除草剂,例如耐受咪唑啉酮类如咪草啶酸(imazamox)的Clearfield夏播油菜(Canola,德国BASFSE)。使用基因工程方法使栽培植物如大豆、棉花、玉米、甜菜和油菜耐受除草剂如草甘膦和草铵膦,它们中的一些可以以商标名RoundupReady(耐受草甘膦,Monsanto,U.S.A.)和LibertyLink(耐受草铵膦,德国BayerCropScience)得到。
此外,还包括通过使用重组DNA技术能够合成一种或多种杀虫蛋白,尤其是由芽孢杆菌属(Bacillus)细菌菌株,特别是苏云金芽孢杆菌(Bacillusthuringiensis)已知的那些的植物,所述杀虫蛋白如-内毒素,例如CryIA(b)、CryIA(c)、CryIF、CryIF(a2)、CryIIA(b)、CryIIIA、CryIIIB(b1)或Cry9c;无性杀虫蛋白(VIP),例如VIP1、VIP2、VIP3或VIP3A;线虫定殖细菌的杀虫蛋白,例如发光杆菌属(Photorhabdus)或致病杆菌属(Xenorhabdus);动物产生的毒素如蝎子毒素、蜘蛛毒素、黄蜂毒素或其他昆虫特异性神经毒素;真菌产生的毒素,例如链霉菌属(Streptomycetes)毒素;植物凝集素,例如豌豆或大麦凝集素;凝集素,蛋白酶抑制剂,例如胰蛋白酶抑制剂,丝氨酸蛋白酶抑制剂,马铃薯储藏蛋白酶抑制剂(patatin),半胱氨酸蛋白酶抑制剂或木瓜蛋白酶抑制剂,核糖体失活蛋白(RIP),例如蓖麻蛋白、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白、皂草素或异株腹泻毒蛋白(bryodin);类固醇代谢酶,例如3-羟基类固醇氧化酶、蜕皮甾类-IDP糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA还原酶;离子通道阻断剂,例如钠通道或钙通道阻断剂;保幼激素酯酶;利尿激素受体(螺旋激肽(helicokinin)受体);茋合成酶,联苄合成酶,壳多糖酶或葡聚糖酶。就本发明而言,这些杀虫蛋白或毒素还应具体理解为前毒素、杂合蛋白、截短的或其他方面改性的蛋白。杂合蛋白的特征在于蛋白域的新型组合(例如参见WO02/015701)。该类毒素或能够合成这些毒素的基因修饰植物的其他实例例如公开于EP-A374753、WO93/007278、WO95/34656、EP-A427529、EP-A451878、WO03/18810和WO03/52073中。生产这些基因修饰植物的方法对本领域技术人员通常是已知的且例如描述于上述出版物中。这些含于基因修饰植物中的杀虫蛋白赋予产生这些蛋白的植物以对所有分类学上为节肢动物的害虫,尤其是甲虫(鞘翅目(Coeleropta))、双翅目昆虫(双翅目(Diptera))和蛾(鳞翅目(Lepidoptera))以及线虫(线虫纲(Nematoda))的耐受性。能够合成一种或多种杀虫蛋白的基因修饰植物例如描述于上述出版物中,它们中的一些可市购,例如YieldGard(产生毒素Cry1Ab的玉米品种),YieldGardPlus(产生毒素Cry1Ab和Cry3Bb1的玉米品种),Starlink(产生毒素Cry9c的玉米品种),HerculexRW(产生毒素Cry34Ab1、Cry35Ab1和酶膦丝菌素-N-乙酰转移酶[PAT]的玉米品种);NuCOTN33B(产生毒素Cry1Ac的棉花品种),BollgardI(产生毒素Cry1Ac的棉花品种),BollgardII(产生毒素Cry1Ac和Cry2Ab2的棉花品种);VIPCOT(产生VIP毒素的棉花品种);NewLeaf(产生毒素Cry3A的土豆品种);Bt-Xtra,NatureGard,KnockOut,BiteGard,Protecta,Bt11(例如AgrisureCB)和法国SyngentaSeedsSAS的Bt176(产生毒素Cry1Ab和PAT酶的玉米品种),法国SyngentaSeedsSAS的MIR604(产生毒素Cry3A的修饰译本的玉米品种,参见WO03/018810),比利时MonsantoEuropeS.A.的MON863(产生毒素Cry3Bb1的玉米品种),比利时MonsantoEuropeS.A.的IPC531(产生毒素Cry1Ac的修饰译本的棉花品种)和比利时PioneerOverseasCorporation的1507(产生毒素Cry1F和PAT酶的玉米品种)。
此外,还包括通过使用重组DNA技术能够合成一种或多种蛋白质以提高对细菌、病毒或真菌病原体的耐受性或抵抗性的植物。这类蛋白质的实例为所谓的“与发病机理相关的蛋白”(PR蛋白,例如参见EP-A392225),植物病害抗性基因(例如表达对来自野生墨西哥土豆Solanumbulbocastanum的致病疫霉(Phytophthorainfestans)起作用的抗性基因的土豆栽培品种)或T4溶菌酶(例如能够合成这些蛋白而对细菌如Erwiniaamylvora具有提高的耐受性的土豆栽培品种)。生产这类基因修饰植物的方法通常为本领域技术人员所已知并且例如描述于上述出版物中。
此外,还包括通过使用重组DNA技术能够合成一种或多种蛋白质以提高产量(例如生物质产量、谷粒产量、淀粉含量、油含量或蛋白质含量),对干旱、盐或其他生长限制环境因素的耐受性或对害虫以及真菌、细菌或其病毒病原体的耐受性的植物。
此外,还包括尤其为了改善人类或动物营养而通过使用重组DNA技术含有改变量的物质含量或新物质含量的植物,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油料作物(例如Nexera油菜,加拿大DOWAgroSciences)。
此外,还包括尤其为了改进原料生产而通过使用重组DNA技术含有改变量的物质含量或新物质含量的植物,例如产生增加的支链淀粉含量的土豆(例如Amflora土豆,德国BASFSE)。
本发明式I的尿嘧啶还可以用于由于基因工程或育种而耐受一种或多种除草剂、由于基因工程或育种而耐受一种或多种病原体如植物病原性真菌或者由于基因工程或育种而耐受昆虫侵袭的农作物。
合适的例如是农作物,优选玉米、小麦、向日葵、甘蔗、棉花、稻、卡罗拉(canola)、油菜籽油菜或大豆,这些作物耐受除草的PPO抑制剂,或者由于通过基因修饰引入用于Bt毒素的基因而耐受某些昆虫侵袭的农作物。
此外,已经发现式I的尿嘧啶还适于植物部分的脱叶和/或干燥,对此合适的是农作物如棉花、土豆、油菜籽油菜、向日葵、大豆或蚕豆,尤其是棉花。就此而言,已经发现用于植物干燥和/或脱叶的组合物、制备这些组合物的方法以及使用式I的尿嘧啶使植物干燥和/或脱叶的方法。
作为干燥剂,式I的尿嘧啶特别适于干燥农作物如土豆、油菜籽油菜、向日葵和大豆以及禾谷类的地上部分。这使得这些重要农作物的完全机械化收获成为可能。
还具有经济益处的是促进柑橘类水果、橄榄和其他品种的仁果、核果和坚果的收获,这通过在一定时间期限内集中裂开或降低对树的粘附而成为可能。相同的机理,即促进水果部分或叶部分与植物的枝部分之间产生脱离组织对于有用植物,尤其是棉花的受控脱叶也是必要的。
此外,各棉花植株成熟的时间间隔缩短导致收获后的纤维质量提高。
式I的尿嘧啶或包含式I的尿嘧啶的除草组合物例如可以以即喷水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液或分散体,乳液,油分散体,糊,粉剂,撒播用材料或颗粒的形式通过喷雾、雾化、撒粉、撒播、浇灌或处理种子或与种子混合而使用。使用形式取决于意欲的目的;在每种情况下都应确保本发明活性成分的最佳可能分布。
除草组合物包含除草有效量的至少一种式I的尿嘧啶和常用于配制作物保护剂的助剂。
常用于配制作物保护剂的助剂实例是惰性助剂,固体载体,表面活性剂(如分散剂、保护性胶体、乳化剂、润湿剂和增粘剂),有机和无机增稠剂,杀菌剂,防冻剂,消泡剂,任选还有着色剂以及用于种子配制剂的粘合剂。
本领域技术人员充分知晓该类配制剂的配方。
增稠剂(即赋予配制剂以改性的流动性能,即静止状态下的高粘度和运动状态下的低粘度的化合物)的实例是多糖,如黄原胶(来自Kelco的Kelzan),Rhodopol23(RhonePoulenc)或Veegum(来自R.T.Vanderbilt),以及有机和无机层状矿物,如Attaclay(来自Engelhard)。
消泡剂实例是聚硅氧烷乳液(如SilikonSRE,Wacker或Rhodorsil,来自Rhodia),长链醇,脂肪酸,脂肪酸盐,有机氟化合物及其混合物。
可以加入杀菌剂以稳定含水除草配制剂。杀菌剂实例是基于双氯芬和苄醇半缩甲醛的杀菌剂(ICI的Proxel或ThorChemie的ActicideRS以及Rohm&Haas的KathonMK),还有异噻唑啉酮衍生物,如烷基异噻唑啉酮类和苯并异噻唑啉酮类(ThorChemie的ActicideMBS)。
防冻剂实例是乙二醇、丙二醇、脲或甘油。
着色剂的实例是微水溶性颜料和水溶性染料。可以提到的实例是以如下名称已知的染料:若丹明B,C.I.颜料红112和C.I.溶剂红1,以及颜料蓝15:4,颜料蓝15:3,颜料蓝15:2,颜料蓝15:1,颜料蓝80,颜料黄1,颜料黄13,颜料红112,颜料红48:2,颜料红48:1,颜料红57:1,颜料红53:1,颜料橙43,颜料橙34,颜料橙5,颜料绿36,颜料绿7,颜料白6,颜料棕25,碱性紫10,碱性紫49,酸性红51,酸性红52,酸性红14,酸性蓝9,酸性黄23,碱性红10,碱性红108。
粘合剂的实例是聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤基乙酸钠。
合适的惰性助剂例如为下列物质:中沸点到高沸点的矿物油馏分如煤油和柴油,此外还有煤焦油和植物或动物来源的油,脂族、环状和芳族烃如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮类如环己酮或强极性溶剂,例如胺类如N-甲基吡咯烷酮,以及水。
合适的载体包括液体和固体载体。液体载体例如包括非水溶剂如环状和芳族烃类,例如石蜡,四氢化萘,烷基化萘及其衍生物,烷基化苯及其衍生物,醇类如甲醇、乙醇、丙醇、丁醇和环己醇,酮类如环己酮或强极性溶剂,例如胺类如N-甲基吡咯烷酮,以及水,及其混合物。
固体载体例如包括矿土如硅石、硅胶、硅酸盐、滑石、高岭土、石灰石、石灰、白垩、红玄武土、黄土、粘土、白云石、硅藻土、硫酸钙、硫酸镁和氧化镁,磨碎的合成材料,肥料如硫酸铵、磷酸铵、硝酸铵和脲类以及植物来源的产品如谷粉、树皮粉、木粉和坚果壳粉,纤维素粉或其它固体载体。
合适的表面活性剂(助剂、润湿剂、增粘剂、分散剂和乳化剂)是芳族磺酸如木素磺酸(例如Borrespers类型,Borregaard)、苯酚磺酸、萘磺酸(Morwet类型,AkzoNobel)和二丁基萘磺酸(Nekal类型,BASFSE)以及脂肪酸的碱金属盐、碱土金属盐和铵盐,烷基-和烷基芳基磺酸盐,烷基硫酸盐,月桂基醚硫酸盐和脂肪醇硫酸盐,以及硫酸化十六-、十七-和十八烷醇的盐,还有脂肪醇乙二醇醚的盐,磺化萘及其衍生物与甲醛的缩合物,萘或萘磺酸与苯酚和甲醛的缩合物,聚氧乙烯辛基酚醚,乙氧基化异辛基-、辛基-或壬基酚,烷基苯基或三丁基苯基聚乙二醇醚,烷基芳基聚醚醇,异十三烷醇,脂肪醇/氧化乙烯缩合物,乙氧基化蓖麻油,聚氧乙烯烷基醚或聚氧丙烯烷基醚,月桂醇聚乙二醇醚乙酸酯,山梨糖醇酯,木素亚硫酸盐废液和蛋白质,变性蛋白质,多糖(如甲基纤维素),疏水改性的淀粉,聚乙烯醇(Mowiol类型,Clariant),聚羧酸盐类(BASFSE,Sokalan类型),聚烷氧基化物,聚乙烯胺(BASFSE,Lupamine类型),聚乙烯亚胺(BASFSE,Lupasol类型),聚乙烯基吡咯烷酮及其共聚物。
粉末、撒播材料和粉剂可以通过将活性成分与固体载体混合或同时研磨来制备。
颗粒如包衣颗粒、浸渍颗粒和均质颗粒可以通过使活性成分与固体载体粘附而制备。
含水使用形式可以通过添加水由乳液浓缩物、悬浮液、糊、可湿性粉末或水分散性颗粒制备。
为了制备乳液、糊或油分散体,可以借助湿润剂、增粘剂、分散剂或乳化剂将式I的尿嘧啶直接或溶于油或溶剂之后在水中均化。或者还可以制备包含活性化合物、湿润剂、增粘剂、分散剂或乳化剂以及需要的话,溶剂或油的浓缩物,该类浓缩物适于用水稀释。
式I的尿嘧啶在即用型制剂(配制剂)中的浓度可以在宽范围内变化。配制剂通常包含约0.001-98重量%,优选0.01-95重量%至少一种活性成分。活性成分以90-100%,优选95-100%(根据NMR光谱)的纯度使用。
在本发明式I的尿嘧啶的配制剂中,活性成分,例如式I的尿嘧啶,以悬浮、乳化或溶解形式存在。本发明配制剂可以呈水溶液,粉末,悬浮液以及高度浓缩的水性、油性或其它悬浮液或分散体,含水乳液,含水微乳液,含水悬浮液,油分散体,糊,粉剂,撒播用材料或颗粒的形式。
本发明式I的尿嘧啶例如可以按如下配制:
1.用水稀释的产品
A水溶性浓缩物
将10重量份活性化合物溶于90重量份水或水溶性溶剂中。或者,加入湿润剂或其它助剂。活性化合物经水稀释溶解。这得到活性化合物含量为10重量%的配制剂。
B分散性浓缩物
将20重量份活性化合物溶于70重量份环己酮中并加入10重量份分散剂如聚乙烯基吡咯烷酮。用水稀释得到分散体。活性化合物含量为20重量%。C可乳化浓缩物
将15重量份活性化合物溶于75重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。用水稀释得到乳液。该配制剂的活性化合物含量为15重量%。
D乳液
将25重量份活性化合物溶于35重量份有机溶剂(如烷基芳烃)中并加入十二烷基苯磺酸钙和蓖麻油乙氧基化物(在每种情况下为5重量份)。借助乳化机(Ultraturrax)将该混合物引入30重量份水中并制成均相乳液。用水稀释得到乳液。该配制剂的活性化合物含量为25重量%。
E悬浮液
在搅拌的球磨机中,将20重量份活性化合物粉碎并加入10重量份分散剂和湿润剂以及70重量份水或有机溶剂,得到细碎活性化合物悬浮液。用水稀释得到稳定的活性化合物悬浮液。该配制剂中活性化合物含量为20重量%。
F水分散性颗粒和水溶性颗粒
将50重量份活性化合物细碎研磨并加入50重量份分散剂和湿润剂,借助工业装置(如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为50重量%。
G水分散性粉末和水溶性粉末
将75重量份活性化合物在转子-定子磨机中研磨并加入25重量份分散剂、湿润剂和硅胶。用水稀释得到稳定的活性化合物分散体或溶液。该配制剂的活性化合物含量为75重量%。
H凝胶配制剂
在球磨机中混合20重量份活性化合物、10重量份分散剂、1重量份胶凝剂和70重量份水或有机溶剂,得到细悬浮液。用水稀释得到活性化合物含量为20重量%的稳定悬浮液。
2.不经稀释而施用的产品
I粉剂
将5重量份活性化合物细碎研磨并与95重量份细碎高岭土充分混合。这得到活性化合物含量为5重量%的撒粉粉末。
J颗粒(GR,FG,GG,MG)
将0.5重量份活性化合物细碎研磨并结合99.5重量份载体。现行方法是挤出、喷雾干燥或流化床方法。这得到不经稀释而施用的活性化合物含量为0.5重量%的颗粒。
KULV溶液(UL)
将10重量份活性化合物溶于90重量份有机溶剂如二甲苯中。这得到不经稀释而施用的活性化合物含量为10重量%的产品。
含水使用形式可以通过添加水由乳液浓缩物、悬浮液、糊、可湿性粉末或水分散性颗粒制备。
式I的尿嘧啶或包含它们的除草组合物可以在出苗前、出苗后或种植之前施用,或者与农作物的种子一起施用。还可以通过施用用除草组合物或活性化合物预处理的农作物的种子而施用除草组合物或活性化合物。若活性成分不能被某些农作物良好地耐受,则可以使用其中借助喷雾设备喷雾除草组合物以使它们尽可能不接触敏感农作物的叶子,而使活性成分到达生长在下面的不希望的植物的叶子或裸露的土壤表面的施用技术(后引导,最后耕作程序)。
在另一实施方案中,可以通过处理种子而施用式I的尿嘧啶或除草组合物。种子的处理基本包括所有本领域技术人员熟知的基于本发明式I的尿嘧啶或由其制备的组合物的程序(拌种、种子包衣、种子撒粉、种子浸泡、种子包膜、种子多层包衣、种子包壳、种子浸滴和种子造粒)。此时可以加以稀释或不加稀释地施用除草组合物。
术语“种子”包括所有类型的种子,如玉米、种子、果实、块茎、秧苗和类似形式。这里优选术语种子描述的是玉米和种子。所用种子可以是上述有用植物的种子,还可以是转基因植物或通过常规育种方法得到的植物的种子。
本发明式I的活性尿嘧啶的施用率(尿嘧啶I的总量)为0.1-3000g/ha,优选10-1000g/ha活性物质(a.s.),取决于防治目标、季节、目标植物和生长阶段。
在本发明的另一优选实施方案中,式I的尿嘧啶的施用率为0.1-5000g/ha,优选1-2500g/ha或5-2000g/ha活性物质(a.s.)。
在本发明的另一优选实施方案中,式I的尿嘧啶的施用率为0.1-1000g/ha,优选1-750g/ha,更优选5-500g/ha活性物质。
为了处理种子,式I的尿嘧啶通常以0.001-10kg/100kg种子的量使用。
为了拓宽作用谱并获得协同增效效果,可以将式I的尿嘧啶与大量其他除草或生长调节活性成分的代表混合,然后联合施用。合适的混合物组分例如为1,2,4-噻二唑类、1,3,4-噻二唑类、酰胺类、氨基磷酸及其衍生物、氨基***类、酰替苯胺类、(杂)芳氧基链烷酸及其衍生物、苯甲酸及其衍生物、苯并噻二嗪酮类、2-芳酰基-1,3-环己烷二酮类、2-杂芳酰基-1,3-环己烷二酮类、杂芳基芳基酮类、苄基异唑烷酮类、间-CF3-苯基衍生物、氨基甲酸酯类、喹啉羧酸及其衍生物、氯代乙酰苯胺类、环己烯酮肟醚衍生物、二嗪类、二氯丙酸及其衍生物、二氢苯并呋喃类、二氢呋喃-3-酮类、二硝基苯胺类、二硝基苯酚类、二苯基醚类、联吡啶类、卤代羧酸及其衍生物、脲类、3-苯基尿嘧啶类、咪唑类、咪唑啉酮类、N-苯基-3,4,5,6-尿嘧啶类、二唑类、环氧乙烷类、酚类、芳氧基-和杂芳氧基苯氧基丙酸酯、苯基乙酸及其衍生物、2-苯基丙酸及其衍生物、吡唑类、苯基吡唑类、哒嗪类、吡啶羧酸及其衍生物、嘧啶基醚类、磺酰胺类、磺酰脲类、三嗪类、三嗪酮类、***啉酮类、***羧酰胺类、尿嘧啶类、苯基吡唑啉类、异唑啉类及其衍生物。
可能有益的是单独或与其他除草剂组合施用式I的尿嘧啶,或者以与其他作物保护试剂的混合物形式施用式I的尿嘧啶,例如与用于防治害虫或植物病原性真菌或细菌的试剂一起施用式I的尿嘧啶。
还令人感兴趣的是与无机盐溶液的溶混性,所述溶液用于处理营养和痕量元素缺乏。还可以加入其他添加剂如非植物毒性油和油浓缩物。
其他除草活性组分B优选选自b1)-b15)类除草剂:
b1)类脂生物合成抑制剂;
b2)乙酰乳酸合成酶抑制剂(ALS抑制剂);
b3)光合成抑制剂;
b4)原卟啉原-IX氧化酶抑制剂,
b5)漂白剂除草剂;
b6)烯醇丙酮酰莽草酸3-磷酸合成酶抑制剂(EPSP抑制剂);
b7)谷氨酰胺合成酶抑制剂;
b8)7,8-二氢蝶酸合成酶抑制剂(DHP抑制剂);
b9)有丝***抑制剂;
b10)非常长链脂肪酸合成抑制剂(VLCFA抑制剂);
b11)纤维素生物合成抑制剂;
b12)去偶剂除草剂;
b13)植物生长素除草剂;
b14)植物生长素输送抑制剂;和
b15)选自溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、indaziflam、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methylazide)、溴甲烷(methylbromide)、苯丙隆(methyl-dymron)、碘甲烷(methyliodide)、甲胂一钠(MSMA)、油酸(oleicacid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(CAS499223-49-3)及其盐和酯的其他除草剂。
优选包含至少一种选自b2、b3、b4、b5、b6、b9和b10类除草剂的除草剂B的那些本发明组合物。
特别优选包含至少一种选自b4、b6和b10类除草剂的除草剂B的那些本发明组合物。
可以与本发明式I的尿嘧啶组合使用的除草剂B实例为:
b1)选自如下的类脂生物合成抑制剂:ACC除草剂如枯杀达(alloxydim)、枯杀达(alloxydim-sodium)、丁氧环酮(butroxydim)、烯草酮(clethodim)、炔草酯(clodinafop)、炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop)、氰氟草酯(cyhalofop-butyl)、氯甲草(diclofop)、禾草灵(diclofop-methyl)、唑禾草灵(fenoxaprop)、唑禾草灵(fenoxaprop-ethyl)、高唑禾草灵(fenoxaprop-P)、高唑禾草灵(fenoxaprop-P-ethyl)、吡氟禾草灵(fluazifop)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵(fluazifop-P-butyl)、吡氟氯禾灵(haloxyfop)、吡氟氯禾灵(haloxyfop-methyl)、精吡氟氯禾灵(haloxyfop-P)、精吡氟氯禾灵(haloxyfop-P-methyl)、唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、喔草酯(propaquizafop)、喹禾灵(quizalofop)、喹禾灵(quizalofop-ethyl)、喹禾灵(四氢糠基酯)(quizalofop-tefuryl)、精喹禾灵(quizalofop-P)、精喹禾灵(quizalofop-P-ethyl)、精喹禾灵(四氢糠基酯)(quizalofop-P-tefuryl)、稀禾定(sethoxydim)、醌肟草(tepraloxydim)和肟草酮(tralkoxydim),以及非ACC除草剂如呋草黄(benfuresate)、苏达灭(butylate)、草灭特(cycloate)、茅草枯(dalapon)、哌草丹(dimepiperate)、扑草灭(EPTC)、禾草畏(esprocarb)、乙呋草黄(ethofumesate)、四氟丙酸(flupropanate)、草达灭(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、TCA、杀草丹(thiobencarb)、丁草威(tiocarbazil)、野麦畏(triallate)和灭草猛(vernolate);
b2)选自如下的ALS抑制剂:磺酰脲类,如磺氨黄隆(amidosulfuron)、四唑黄隆(azimsulfuron)、苄嘧黄隆(bensulfuron)、苄嘧黄隆(bensulfuron-methyl)、氯嘧黄隆(chlorimuron)、氯嘧黄隆(chlorimuron-ethyl)、绿黄隆(chlorsulfuron)、醚黄隆(cinosulfuron)、环丙黄隆(cyclosulfamuron)、胺苯黄隆(ethametsulfuron)、胺苯黄隆(ethametsulfuron-methyl)、乙氧嘧黄隆(ethoxysulfuron)、啶嘧黄隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟定黄隆(flupyrsulfuron)、氟定黄隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、吡氯黄隆(halosulfuron)、吡氯黄隆(halosulfuron-methyl)、啶咪黄隆(imazosulfuron)、碘黄隆(iodosulfuron)、碘甲黄隆钠(iodosulfuron-methyl-sodium)、甲基二磺隆(mesosulfuron)、metazosulfuron、甲黄隆(metsulfuron)、甲黄隆(metsulfuron-methyl)、烟嘧黄隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧黄隆(oxasulfuron)、氟嘧黄隆(primisulfuron)、氟嘧黄隆(primisulfuron-methyl)、propyrisulfuron、氟丙黄隆(prosulfuron)、吡嘧黄隆(pyrazosulfuron)、吡嘧黄隆(pyrazosulfuron-ethyl)、玉嘧黄隆(rimsulfuron)、嘧黄隆(sulfometuron)、嘧黄隆(sulfometuron-methyl)、乙黄黄隆(sulfosulfuron)、噻黄隆(thifensulfuron)、噻黄隆(thifensulfuron-methyl)、醚苯黄隆(triasulfuron)、苯黄隆(tribenuron)、苯黄隆(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)和三氟甲磺隆(tritosulfuron),咪唑啉酮类如咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)和咪草烟(imazethapyr),***并嘧啶类除草剂和磺酰苯胺类如唑嘧磺胺酸(cloransulam)、唑嘧磺胺盐(cloransulam-methyl)、唑嘧磺胺(diclosulam)、氟唑啶草(flumetsulam)、双氟磺草胺(florasulam)、唑草磺胺(metosulam)、五氟磺草胺(penoxsulam)、pyrimisulfan和啶磺草胺(pyroxsulam),嘧啶基苯甲酸酯类如双嘧苯甲酸(bispyribac)、双嘧苯甲酸钠(bispyribac-sodium)、嘧苯草肟(pyribenzoxim)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、肟啶草(pyriminobac-methyl)、嘧硫苯甲酸(pyrithiobac)、嘧硫苯甲酸钠(pyrithiobac-sodium)、4-[[[2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯基]甲基]氨基]苯甲酸1-甲基乙基酯(CAS420138-41-6)、4-[[[2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯基]甲基]氨基]苯甲酸丙基酯(CAS420138-40-5)、N-(4-溴苯基)-2-[(4,6-二甲氧基-2-嘧啶基)氧基]苯甲胺(CAS420138-01-8)以及磺酰氨基羰基***啉酮类除草剂如氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、丙苯磺隆(propoxycarbazon)、丙苯磺隆(propoxycarbazon-sodium)、thiencarbazone和thiencarbazone-methyl。其中本发明的优选实施方案涉及包含至少一种咪唑啉酮类除草剂的那些组合物;
b3)选自如下的光合成抑制剂:胺唑草酮(amicarbazone),光合***II抑制剂,例如三嗪类除草剂,包括氯代三嗪类、三嗪酮类、三嗪二酮类、甲硫基三嗪类和哒嗪酮类除草剂,如莠灭净(ametryn)、莠去津(atrazine)、杀草敏(chloridazone)、草净津(cyanazine)、敌草净(desmetryn)、戊草津(dimethametryn)、六嗪同(hexazinone)、赛克津(metribuzin)、扑灭通(prometon)、扑草净(prometryn)、扑灭津(propazin)、西玛津(simazin)、西草净(simetryn)、甲氧去草净(terbumeton)、特丁津(terbuthylazin)、去草净(terbutryn)和草达津(trietazin);芳基脲类如氯溴隆(chlorobromuron)、绿麦隆(chlorotoluron)、枯草隆(chloroxuron)、丁隆(dimefuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、异恶隆(isouron)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、色满隆(metobenzuron)、甲氧隆(metoxuron)、绿谷隆(monolinuron)、草不隆(neburon)、环草隆(siduron)、丁唑隆(tebuthiuron)和赛二唑素(thidiazuron),苯基氨基甲酸酯类如异苯敌草(desmedipham)、卡草灵(karbutilat)、苯敌草(phenmedipham)、乙苯敌草(phenmedipham-ethyl),腈类除草剂如杀草全(bromofenoxim)、溴苯腈(bromoxynil)及其盐和酯、碘苯腈(ioxynil)及其盐和酯,尿嘧啶类如除草定(bromacil)、环草定(lenacil)和特草定(terbacil),以及噻草平(bentazon)和噻草平(bentazon-sodium),达草止(pyridatre)、pyridafol、蔬草灭(pentanochlor)和敌稗(propanil)以及光合***I抑制剂如敌草快阳离子(diquat)、敌草快(diquat-dibromide)、对草快阳离子(paraquat)、对草快(paraquat-dichloride)和对草快(paraquat-dimetilsulfate)。其中本发明的优选实施方案涉及包含至少一种芳基脲类除草剂的那些组合物。其中本发明的优选实施方案同样涉及包含至少一种三嗪类除草剂的那些组合物。其中本发明的优选实施方案同样涉及包含至少一种腈类除草剂的那些除草剂。
b4)选自如下的原卟啉原-IX氧化酶抑制剂:氟锁草醚(acifluorfen)、氟锁草醚(acifluorfen-sodium)、唑啶炔草(azafenidin)、bencarbazone、双苯嘧草酮(benzfendizone)、治草醚(bifenox)、氟丙嘧草酯(butafenacil)、氟酮唑草(carfentrazone)、氟酮唑草(carfentrazone-ethyl)、氯硝醚(chlomethoxyfen)、吲哚酮草酯(cinidon-ethyl)、异丙吡草酯(fluazolate)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、酰亚胺苯氧乙酸(flumiclorac)、酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚(fluoroglycofen-ethyl)、达草氟(fluthiacet)、达草氟(fluthiacet-methyl)、氟黄胺草醚(fomesafen)、氟硝磺酰胺(halosafen)、乳氟禾草灵(lactofen)、炔丙唑草(oxadiargyl)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊唑草(pentoxazone)、氟唑草胺(profluazol)、双唑草腈(pyraclonil)、氟唑草酯(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、嘧啶肟草醚(saflufenacil)、磺胺草唑(sulfentrazone)、噻二唑胺(thidiazimin)、[3-[2-氯-4-氟-5-(1-甲基-6-三氟甲基-2,4-二氧代-1,2,3,4-四氢嘧啶-3-基)苯氧基]-2-吡啶氧基]乙酸乙酯(CAS353292-31-6;S-3100)、N-乙基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS452098-92-9)、N-四氢糠基-3-(2,6-二氯-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS915396-43-9)、N-乙基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS452099-05-7)、N-四氢糠基-3-(2-氯-6-氟-4-三氟甲基苯氧基)-5-甲基-1H-吡唑-1-甲酰胺(CAS45100-03-7)、3-[7-氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[1,4]嗪-6-基]-1,5-二甲基-6-硫代-[1,3,5]三嗪烷(triazinan)-2,4-二酮、1,5-二甲基-6-硫代-3-(2,2,7-三氟-3-氧代-4-(丙-2-炔基)-3,4-二氢-2H-苯并[b][1,4]嗪-6-基])-1,3,5-三嗪烷-2,4-二酮和2-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[b][1,4]嗪-6-基)-4,5,6,7-四氢异吲哚-1,3-二酮;
b5)选自如下的漂白剂除草剂:PDS抑制剂:氟丁酰草胺(beflubutamid)、吡氟草胺(diflufenican)、氟草同(fluridone)、氟咯草酮(flurochloridone)、呋草酮(flurtamone)、达草灭(norflurazon)、氟吡酰草胺(picolinafen)和4-(3-三氟甲基苯氧基)-2-(4-三氟甲基苯基)嘧啶(CAS180608-33-7),HPPD抑制剂:苯并双环酮(benzobicyclon)、吡草酮(benzofenap)、异氟草(isoxaflutole)、甲基磺草酮(mesotrione)、pyrasulfotole、吡唑特(pyrazolynate)、苄草唑(pyrazoxyfen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、topramezone和bicyclopyrone,漂白剂,未知目标:苯草醚(aclonifen)、杀草强(amitrole)、异恶草酮(clomazone)和flumeturon;
b6)选自如下的EPSP合成酶抑制剂:草甘膦、草甘膦异丙胺盐(glyphosate-isopropylammonium)和草硫膦(glyphosate-trimesium)(sulfosate);
b7)选自如下的谷氨酰胺合成酶抑制剂:双丙氨酰膦(bilanaphos(bialaphos))、双丙氨酰膦(bilanaphos-sodium)、草铵膦、草铵膦(glufosinate-P)和草铵膦(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:黄草灵(asulam);
b9)选自如下的有丝***抑制剂:K1组化合物:二硝基苯胺类如氟草胺(benfluralin)、地乐胺(butralin)、敌乐胺(dinitramine)、丁氟消草(ethalfluralin)、氟消草(fluchloralin)、黄草消(oryzalin)、胺硝草(pendimethalin)、氨基丙氟灵(prodiamine)和氟乐灵(trifluralin),氨基磷酸酯类如胺草磷(amiprophos)、甲基胺草磷(amiprophos-methyl)和草胺磷(butamiphos),苯甲酸类除草剂如敌草索(chlorthal)、敌草索(chlorthal-dimethyl),吡啶类如氟硫草定(dithiopyr)和噻氟啶草(thiazopyr),苯甲酰胺类如拿草特(propyzamide)和丙戊草胺(tebutam),K2组化合物:氯苯胺灵(chlorpropham)、苯胺灵(propham)和长杀草(carbetamide);其中优选K1组化合物,尤其优选二硝基苯胺类;
b10)选自如下的VLCFA抑制剂:氯乙酰胺类如乙草胺(acetochlor)、甲草胺(alachlor)、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethanamid)、精噻吩草胺(dimethenamid-P)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(metolachlor-S)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)和噻醚草胺(thenylchlor),羟基乙酰苯胺类(oxyacetanilide)如氟噻草胺(flufenacet)和苯噻草胺(mefenacet),乙酰苯胺类如草乃敌(diphenamid)、萘丙胺(naproanilide)和草萘胺(napropamide),四唑啉酮类如四唑酰草胺(fentrazamide)以及其他除草剂如莎稗磷(anilofos)、唑草胺(cafenstrole)、fenoxasulfone、ipfencarbazone、哌草磷(piperophos)、派罗克杀草砜(pyroxasulfone);和式II的异唑啉化合物:
其中R21、R22、R23、R24、W、Z和n具有下列含义:
R21、R22、R23、R24相互独立地为氢、卤素或C1-C4烷基;
W为苯基或除了碳环成员外还含有1、2或3个选自氧、氮和硫的相同或不同杂原子作为环成员的单环5、6、7、8、9或10员杂环,其中苯基和杂环基未被取代或带有1、2或3个选自卤素、C1-C4烷基、C1-C4烷氧基、C1-C4卤代烷基和C1-C4卤代烷氧基的取代基Ryy;
优选苯基或除了碳环成员外还含有1、2或3个氮原子作为环成员的5或6员芳族杂环基(杂芳基),其中苯基和杂芳基未被取代或带有1、2或3个取代基Ryy;
Z为氧或NH;以及
n为0或1;
在式II的异唑啉化合物中,优选如下式II的异唑啉化合物,其中R21、R22、R23、R24相互独立地为H、F、Cl或甲基;
Z为氧;
n为0或1;和
W为苯基、吡唑基或1,2,3-***基,其中后提到的三个基团未被取代或带有1、2或3个取代基Ryy,尤其是下列基团之一:
其中
R25为卤素、C1-C4烷基或C1-C4卤代烷基;
R26为C1-C4烷基;
R27为卤素、C1-C4烷氧基或C1-C4卤代烷氧基;
R28为卤素、C1-C4烷基、C1-C4卤代烷基或C1-C4卤代烷氧基;
m为0、1、2或3;和
#表示与基团CR23R24的连接点;
在式II的异唑啉化合物中,尤其优选如下那些式II的异唑啉化合物,其中
R21为氢;
R22为氟;
R23为氢或氟;
R24为氢或氟;
W为式W1、W2、W3或W4的基团之一:
其中#表示与基团CR13R14的连接点;
Z为氧;
n为0或1,尤其是1;以及
其中尤其优选式II.1、II.2、II.3、II.4、II.5、II.6、II.7、II.8和II.9的异唑啉化合物:
式II的异唑啉化合物在现有技术中是已知的,例如由WO2006/024820,WO2006/037945,WO2007/071900和WO2007/096576已知;
在VLCFA抑制剂中,优选氯代乙酰胺类和羟基乙酰胺类;
b11)选自如下的纤维素生物合成抑制剂:草克乐(chlorthiamid)、敌草腈(dichlobenil)、胺草唑(flupoxam)、异恶草胺(isoxaben)、1-环己基-5-五氟苯氧基-14-[1,2,4,6]硫杂三嗪-3-基胺和式III的哌嗪化合物:
其中
A为苯基或吡啶基,其中Ra连接在A与碳原子的连接点的邻位;
Ra为CN、NO2、C1-C4烷基、D-C3-C6环烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、O-D-C3-C6环烷基、S(O)qRy、C2-C6链烯基、D-C3-C6环烯基、C3-C6链烯氧基、C2-C6炔基、C3-C6炔氧基、NRARB、三-C1-C4烷基甲硅烷基、D-C(=O)-Ra1、D-P(=O)(Ra1)2、苯基、萘基、含有1、2、3或4个选自O、N和S的杂原子且可以被基团Raa和/或Ra1部分或完全取代的经由碳或氮连接的3-7员单环或9或10员双环饱和、不饱和或芳族杂环,以及若Ra与碳原子连接,则额外为卤素;
Ry为C1-C6烷基、C3-C4链烯基、C3-C4炔基、NRARB或C1-C4卤代烷基以及q为0、1或2;
RA、RB相互独立地为氢、C1-C6烷基、C3-C6链烯基和C3-C6炔基;RA、RB还可以与它们所连接的氮原子一起形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和、部分或完全不饱和环,该环可以被1-3个基团Raa取代;
D为共价键、C1-C4亚烷基、C2-C6链烯基或C2-C6炔基;
Ra1为氢、OH、C1-C8烷基、C1-C4卤代烷基、C3-C6环烷基、C2-C8链烯基、C5-C6环烯基、C2-C8炔基、C1-C6烷氧基、C1-C4卤代烷氧基、C3-C8链烯氧基、C3-C8炔氧基、NRARB、C1-C6烷氧氨基、C1-C6烷基磺酰氨基、C1-C6烷基氨基磺酰氨基、[二-(C1-C6)烷基氨基]磺酰氨基、C3-C6链烯基氨基、C3-C6炔基氨基、N-(C2-C6链烯基)-N-(C1-C6烷基)氨基、N-(C2-C6炔基)-N-(C1-C6烷基)氨基、N-(C1-C6烷氧基)-N-(C1-C6烷基)氨基、N-(C2-C6链烯基)-N-(C1-C6烷氧基)氨基、N-(C2-C6炔基)-N-(C1-C6烷氧基)氨基、C1-C6烷基磺酰基、三-C1-C4烷基甲硅烷基、苯基、苯氧基、苯基氨基或含有1、2、3或4个选自O、N和S的杂原子的5或6员单环或9或10员双环杂环,其中该环状基团未被取代或被1、2、3或4个基团Raa取代;
Raa为卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、S(O)qRy、D-C(=O)-Ra1和三-C1-C4烷基甲硅烷基;
Rb相互独立地为氢、CN、NO2、卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、苄基或S(O)qRy,Rb与连接于相邻环原子的基团Ra或Rb一起还可以形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和或部分或完全不饱和环,该环可以部分或完全被Raa取代;
p为0、1、2或3;
R30为氢、OH、CN、C1-C12烷基、C3-C12链烯基、C3-C12炔基、C1-C4烷氧基、C3-C6环烷基、C5-C6环烯基、NRARB、S(O)nRy、S(O)nNRARB、C(=O)R40、CONRARB、苯基或含有1、2、3或4个选自O、N和S的杂原子的5或6员单环或9或10员双环芳族杂环,其中该环状基团经由D1连接且未被取代或被1、2、3或4个基团Raa取代,以及下列部分或完全被Raa取代的基团:C1-C4烷基、C3-C4链烯基和C3-C4炔基;
R40为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
D1为羰基或基团D;
其中在基团R15、Ra及其子取代基中,碳链和/或环状基团可以带有1、2、3或4个取代基Raa和/或Ra1;
R31为C1-C4烷基、C3-C4链烯基或C3-C4炔基;
R32为OH、NH2、C1-C4烷基、C3-C6环烷基、C3-C6链烯基、C3-C6炔基、C1-C4羟基烷基、C1-C4氰基烷基、C1-C4卤代烷基、C1-C4烷氧基-C1-C4烷基或C(=O)R40;
R33为氢、卤素、C1-C4烷基或C1-C4卤代烷基,或者R33和R34一起为共价键;
R34、R35、R36、R37相互独立地为氢、卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C2-C6链烯基、C2-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、C3-C6环烷基、C3-C6环烯基和C3-C6环炔基;
R38、R39相互独立地为氢、卤素、OH、卤代烷基、NRARB、NRAC(O)R41、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、O-C(O)R41、苯氧基或苄氧基,其中在基团R38和R39中碳链和/或环状基团可以带有1、2、3或4个取代基Raa;
R41为C1-C4烷基或NRARB;
在式III哌嗪化合物中,优选如下式III的哌嗪化合物,其中A为苯基或吡啶基,其中Ra连接在A与碳原子的连接点的邻位;
Ra为CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或D-C(=O)-Ra1;
Ry为C1-C6烷基、C3-C4链烯基、C3-C4炔基、NRARB或C1-C4卤代烷基以及q为0、1或2;
RA、RB相互独立地为氢、C1-C6烷基、C3-C6链烯基和C3-C6炔基;RA、RB还可以与它们所连接的氮原子一起形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和、部分或完全不饱和环,该环可以被1-3个基团Raa取代;
D为共价键或C1-C4亚烷基;
Ra1为氢、OH、C1-C8烷基、C1-C4卤代烷基、C3-C6环烷基;
Raa为卤素、OH、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、S(O)qRy、D-C(=O)-Ra1和三-C1-C4烷基甲硅烷基;
Rb相互独立地为CN、NO2、卤素、C1-C4烷基、C1-C4卤代烷基、C2-C4链烯基、C3-C6炔基、C1-C4烷氧基、C1-C4卤代烷氧基、苄基或S(O)qRy,Rb与连接于相邻环原子的基团Ra或Rb一起还可以形成除了碳原子外可以含有1、2或3个选自O、N和S的杂原子的5或6员饱和或部分或完全不饱和环,该环可以部分或完全被Raa取代;
p为0或1;
R30为氢、C1-C12烷基、C3-C12链烯基、C3-C12炔基、C1-C4烷氧基或C(=O)R40;
R40为氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
其中在基团R30、Ra及其子取代基中,碳链和/或环状基团可以带有1、2、3或4个取代基Raa和/或Ra1;
R31为C1-C4烷基;
R32为OH、NH2、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基或C(=O)R25;
R33为氢,或者R33和R34一起为共价键;
R34、R35、R36、R37相互独立地为氢;
R38、R39相互独立地为氢、卤素或OH;
b12)选自如下的去偶剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的植物生长素除草剂:2,4-D及其盐和酯、2,4-DB及其盐和酯、氨草啶(aminopyralid)及其盐如氨草啶铵盐(aminopyralid-tris(2-hydroxypropyl)ammonium)及其酯、草除灵(benazolin)、草除灵(benazolin-ethyl)、草灭平(chloramben)及其盐和酯、稗草胺(clomeprop)、二氯皮考啉酸(clopyralid)及其盐和酯、麦草畏(dicamba)及其盐和酯、2,4-滴丙酸(dichlorprop)及其盐和酯、高2,4-滴丙酸(dichlorprop-P)及其盐和酯、氟草烟(fluroxypyr)、氟草烟(fluroxypyr-butometyl)、氟氯胺啶(fluroxypyr-meptyl)、MCPA及其盐和酯、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB及其盐和酯、2甲4氯丙酸(mecoprop)及其盐和酯、高2甲4氯丙酸(mecoprop-P)及其盐和酯、毒莠定(picloram)及其盐和酯、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、TBA(2,3,6)及其盐和酯、绿草定(triclopyr)及其盐和酯以及aminocyclopyrachlor及其盐和酯;
b14)选自如下的植物生长素输送抑制剂:二氟吡隆(diflufenzopyr)、二氟吡隆(diflufenzopyr-sodium)、抑草生(naptalam)和抑草生(naptalam-sodium);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、indaziflam、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methylazide)、溴甲烷(methylbromide)、苯丙隆(methyl-dymron)、碘甲烷(methyliodide)、甲胂一钠(MSMA)、油酸(oleicacid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇(CAS499223-49-3)及其盐和酯。
此外,可能有用的是将式I的尿嘧啶与安全剂组合施用。安全剂是防止或降低对有用植物的损害但不对式I的尿嘧啶对不希望的植物的除草作用具有显著影响的化合物。它们可以在播种之前施用(例如在种子处理时、在枝或秧苗上)或以有用植物的出苗前或出苗后施用方式施用。安全剂和式I的尿嘧啶可以同时或依次施用。
合适的安全剂例如是(喹啉-8-氧基)乙酸类、1-苯基-5卤代烷基-1H-1,2,4-***-3-羧酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二羧酸、4,5-二氢-5,5-二芳基-3-异唑羧酸、二氯乙酰胺类、α-肟基苯基乙腈、苯乙酮肟类、4,6-二卤代-2-苯基嘧啶类、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺类、1,8-萘二甲酸酐、2-卤代-4-卤代烷基-5-噻唑羧酸、硫代磷酸酯类和N-烷基-O-苯基氨基甲酸酯类及其可农用盐和可农用衍生物如酰胺、酯和硫酯,条件是它们具有酸基。
优选安全剂C的实例是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、抑害胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
尤其优选的安全剂C是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、cyprosulfamide、抑害胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
特别优选的安全剂C是解草酮(benoxacor)、喹氧乙酸(cloquintocet)、cyprosulfamide、抑害胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalicanhydride)、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS52836-31-4)。
b1)-b15)组活性化合物和安全剂C是已知的除草剂和安全剂,例如参见TheCompendiumofPesticideCommonNames(http://www.alanwood.net/pesticides/);B.Hock,C.Fedtke,R.R.Schmidt,Herbizide[除草剂],GeorgThiemeVerlag,Stuttgart,1995。其他除草活性化合物由WO96/26202,WO97/41116,WO97/41117,WO97/41118,WO01/83459和WO2008/074991以及W.等(编辑)“ModernCropProtectionCompounds”,第1卷,WileyVCH,2007及其中所引用的文献已知。
本发明还涉及配制成单组分组合物的作物保护组合物形式的组合物,该单组分组合物包含含有至少一种式I的尿嘧啶或至少一种其他活性化合物,优选选自b1-b15组的活性化合物的活性化合物组合,以及至少一种固体或液体载体和/或一种或多种表面活性剂以及需要的话一种或多种常用于作物保护组合物的其他助剂。
本发明还涉及配制成双组分组合物的作物保护组合物形式的组合物,该双组分组合物包含第一组分和第二组分,该第一组分包含至少一种式I的尿嘧啶、固体或液体载体和/或一种或多种表面活性剂,该第二组分包含至少一种选自b1-b15组活性化合物的其他活性化合物、固体或液体载体和/或一种或多种表面活性剂,其中这两种组分还可以额外地包含常用于作物保护组合物的其他助剂。
在包含至少一种式I化合物作为组分A和至少一种除草剂B的二元组合物中,活性化合物A∶B的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
在包含至少一种式I化合物作为组分A和至少一种安全剂C的二元组合物中,活性化合物A∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
在包含至少一种式I化合物作为组分A、至少一种除草剂B和至少一种安全剂C的三元组合物中,组分A∶B的相对重量份通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1;组分A∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1;以及组分B∶C的重量比通常为1∶1000-1000∶1,优选1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。优选组分A+B与组分C的重量比为1∶500-500∶1,尤其是1∶250-250∶1,特别优选1∶75-75∶1。
特别优选的除草剂B是如上所定义的除草剂B;尤其是下表B所列除草剂B.1-B.143:
表B:
作为组分C构成本发明组合物的成分的特别优选安全剂C是如上所定义的安全剂C,尤其是下表C所列安全剂C.1-C.12:
表C
各组分在下面所述优选混合物中的重量比在上面所给限度内,尤其是优选限度内。
特别优选如下所述的组合物:
包含所定义的式I的尿嘧啶和如表1相应行所定义的物质;
尤其优选包含所定义的式I的尿嘧啶作为唯一的除草活性化合物和如表1相应行所定义的物质;
最优选包含所定义的式I的尿嘧啶作为唯一的活性化合物和如表1相应行所定义的物质。
特别优选组合物1.1-1.1871,其包含尿嘧啶Ia48和如表1相应行所定义的物质:
表1(组合物1.1-1.1871):
各单一组合物的特殊编号可按如下推导:
组合物1.777例如包含尿嘧啶Ia48、苯嗪草(B.62)和解草唑(C.5)(见表1,第1.777项;以及表B,第B.62项和表C,第C.5项)。
组合物2.777例如包含尿嘧啶Ib48、苯嗪草(B.62)和解草唑(C.5)(见下面组合物2.1-2.1871的定义以及表1,第1.777项;表B,第B.62项和表C,第C.5项)。
组合物7.777例如包含甲基咪草烟(B30)以及尿嘧啶Ia48、苯嗪草(B.62)和解草唑(C.5)(见下面组合物7.1-7.1871的定义以及表1,第1.777项;表B,第B.62项和表C,第C.5项)。
还尤其优选组合物2.1.-2.1871,其与对应组合物1.1-1.1871的不同仅在于它们包含尿嘧啶Ib48作为活性化合物A。
还尤其优选组合物3.1.-3.1871,其与对应组合物1.1-1.1871的不同仅在于它们包含尿嘧啶Ic48作为活性化合物A。
还尤其优选组合物4.1.-4.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.2作为其他除草剂B。
还尤其优选组合物5.1.-5.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.7作为其他除草剂B。
还尤其优选组合物6.1.-6.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.29作为其他除草剂B。
还尤其优选组合物7.1.-7.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.30作为其他除草剂B。
还尤其优选组合物8.1.-8.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.31作为其他除草剂B。
还尤其优选组合物9.1.-9.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.32作为其他除草剂B。
还尤其优选组合物10.1.-10.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.33作为其他除草剂B。
还尤其优选组合物11.1.-11.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.40作为其他除草剂B。
还尤其优选组合物12.1.-12.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.44作为其他除草剂B。
还尤其优选组合物13.1.-13.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.45作为其他除草剂B。
还尤其优选组合物14.1.-14.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.52作为其他除草剂B。
还尤其优选组合物15.1.-15.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.53作为其他除草剂B。
还尤其优选组合物16.1.-16.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.54作为其他除草剂B。
还尤其优选组合物17.1.-17.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.55作为其他除草剂B。
还尤其优选组合物18.1.-18.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.56作为其他除草剂B。
还尤其优选组合物19.1.-19.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.57作为其他除草剂B。
还尤其优选组合物20.1.-20.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.60作为其他除草剂B。
还尤其优选组合物21.1.-21.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.65作为其他除草剂B。
还尤其优选组合物22.1.-22.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.66作为其他除草剂B。
还尤其优选组合物23.1.-23.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.69作为其他除草剂B。
还尤其优选组合物24.1.-24.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.72作为其他除草剂B。
还尤其优选组合物25.1.-25.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.73作为其他除草剂B。
还尤其优选组合物26.1.-26.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.76作为其他除草剂B。
还尤其优选组合物27.1.-27.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.77作为其他除草剂B。
还尤其优选组合物28.1.-28.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.82作为其他除草剂B。
还尤其优选组合物29.1.-29.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.83作为其他除草剂B。
还尤其优选组合物30.1.-30.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.86作为其他除草剂B。
还尤其优选组合物31.1.-31.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.86和B.54作为其他除草剂B。
还尤其优选组合物32.1.-32.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.86和B.60作为其他除草剂B。
还尤其优选组合物33.1.-33.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.86和B.66作为其他除草剂B。
还尤其优选组合物34.1.-34.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.87作为其他除草剂B。
还尤其优选组合物35.1.-35.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.87和B.54作为其他除草剂B。
还尤其优选组合物36.1.-36.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.87和B.60作为其他除草剂B。
还尤其优选组合物37.1.-37.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.87和B.66作为其他除草剂B。
还尤其优选组合物38.1.-38.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.89作为其他除草剂B。
还尤其优选组合物39.1.-39.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.90作为其他除草剂B。
还尤其优选组合物40.1.-40.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.90和B.54作为其他除草剂B。
还尤其优选组合物41.1.-41.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.90和B.60i作为其他除草剂B。
还尤其优选组合物42.1.-42.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.90和B.66作为其他除草剂B。
还尤其优选组合物43.1.-43.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.92作为其他除草剂B。
还尤其优选组合物44.1.-44.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.93作为其他除草剂B。
还尤其优选组合物45.1.-45.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.93和B.54作为其他除草剂B。
还尤其优选组合物46.1.-46.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.93和B.60作为其他除草剂B。
还尤其优选组合物47.1.-47.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.93和B.66作为其他除草剂B。
还尤其优选组合物48.1.-48.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97作为其他除草剂B。
还尤其优选组合物49.1.-49.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.54作为其他除草剂B。
还尤其优选组合物50.1.-50.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.76作为其他除草剂B。
还尤其优选组合物51.1.-51.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.86作为其他除草剂B。
还尤其优选组合物52.1.-52.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.87作为其他除草剂B。
还尤其优选组合物53.1.-53.1871,其与对应组合物1.1-1.1871的不同仅在发于它们额外包含B.97和B.90作为其他除草剂B。
还尤其优选组合物54.1.-54.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.93作为其他除草剂B。
还尤其优选组合物55.1.-55.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.97和B.105作为其他除草剂B。
还尤其优选组合物56.1.-56.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.100作为其他除草剂B。
还尤其优选组合物57.1.-57.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.103作为其他除草剂B。
还尤其优选组合物58.1.-58.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.105作为其他除草剂B。
还尤其优选组合物59.1.-59.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.108作为其他除草剂B。
还尤其优选组合物60.1.-60.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.109作为其他除草剂B。
还尤其优选组合物61.1.-61.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.110作为其他除草剂B。
还尤其优选组合物62.1.-62.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.112作为其他除草剂B。
还尤其优选组合物63.1.-63.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.114作为其他除草剂B。
还尤其优选组合物64.1.-64.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.115作为其他除草剂B。
还尤其优选组合物65.1.-65.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.119作为其他除草剂B。
还尤其优选组合物66.1.-66.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.121作为其他除草剂B。
还尤其优选组合物67.1.-67.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.122作为其他除草剂B。
还尤其优选组合物68.1.-68.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.124作为其他除草剂B。
还尤其优选组合物69.1.-69.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.125作为其他除草剂B。
还尤其优选组合物70.1.-70.1871,其与对应组合物1.1-1.1871的不同仅在于它们额外包含B.132作为其他除草剂B。
实施例
下文通过实施例说明式I的尿嘧啶的制备;然而,本发明主题并不限于所给实施例。
实施例1:
1-甲基-6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并
1.1:2-氨基-5-氟苯酚
在N2气氛下向在乙醇中的5-氟-2-硝基苯酚(26.63g,170mmol)中加入碳载钯(10重量%,250mg,0.235mmol)。将该混合物用H2吹扫并在室温下在H2(气球)下搅拌直到根据薄层色谱(TLC)分析完全转化。通过过滤除去Pd/C并将滤液浓缩而得到21.6g标题化合物。
1HNMR(DMSO):4.5(br,2H),6.35(dd,1H),6.45(dd,1H),6.50(dd,1H),9.5(br,1H)。
1.2:2-溴-2,2-二氟-N-(4-氟-2-羟基苯基)乙酰胺
方案a)
在0℃下向无水四氢呋喃中的2-氨基-5-氟苯酚(14g,110mmol)中加入氢化钠(55重量%,在矿物油中;4.81g,110mmol)。将所得混合物在-15℃下搅拌15分钟。然后滴加2-溴-2,2-二氟乙酸乙酯(24.59g,121mmol)并将所得混合物在0℃下搅拌2小时。将反应混合物用饱和NH4Cl水溶液终止并用乙酸乙酯萃取。合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到33g标题化合物。
1HNMR(DMSO):3.3(br,1H),6.8(m,2H),7.25(dd,1H),10.4(br,1H)。方案b)
在0℃下向无水四氢呋喃中的2-氨基-5-氟苯酚(200mg,1.573mmol)中加入氢化钠(55重量%,在矿物油中;68.6mg,1.573mmol)。将所得混合物在-15℃下搅拌15分钟。然后滴加2-溴-2,2-二氟乙酸甲酯(327mg,1.731mmol)并将所得混合物在0℃下搅拌2小时。将反应混合物在饱和NH4Cl水溶液中终止并用乙酸乙酯萃取。将合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到450mg标题化合物。
1HNMR(DMSO):3.3(br,1H),6.8(m,2H),7.25(dd,1H),10.4(br,1H)。
向无水甲苯中的2-溴-2,2-二氟-N-(4-氟-2-羟基苯基)乙酰胺(33g,116mmol)中加入1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU,17.51ml,116mmol)。将所得混合物在80℃下搅拌过夜。将该反应在饱和NH4Cl水溶液中终止并用乙酸乙酯萃取。将合并的萃取液用盐水洗涤,用Na2SO4干燥并浓缩而得到24.94g标题化合物。
GCMSm/e(M+)=203
将2,2,7-三氟-2H-苯并[b][1,4]嗪-3(4H)-酮(2.5g,12.31mmol)溶于硫酸(40ml,750mmol)中。将反应混合物冷却至0-5℃。缓慢滴加硝酸(1.761ml,39.7mmol)并将温度维持为0-5℃。将反应混合物在该温度下搅拌30分钟。然后将反应混合物滴加到剧烈搅拌的冷水中。形成固体,将其用二氯甲烷提取。将合并的提取液在Na2SO4上干燥并浓缩而以褐色固体得到2.56g标题化合物。
GC/MSm/e(M+)=248
1H-NMR(CDCl3):2.90(br,1H),7.15(d,1H),7.80(d,1H)。
在室温下向无水N,N-二甲基甲酰胺中的2,2,7-三氟-6-硝基-2H-苯并[b][1,4]嗪-3(4H)-酮(6.9g,27.8mmol)和碳酸钾(4.61g,33.4mmol)中滴加3-溴丙-1-炔(80重量%,在甲苯中;4.96g,33.4mmol)。将所得混合物在室温下搅拌过夜。将反应混合物倾入饱和NH4Cl水溶液中并用乙酸乙酯萃取。将合并的萃取液用NaCl水溶液洗涤,用Na2SO4干燥,浓缩并用甲苯捕集而以深褐色固体得到7.06g标题化合物。
GCMSm/e(M+)=286
1.6:6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮
向在水中的氯化铵(3.96g,74.0mmol)中加入铁粉(325目;4.13g,74.0mmol)。向所得混合物中加入在甲醇/四氢呋喃中的2,2,7-三氟-6-硝基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(7.06g,24.67mmol)。在70℃下将所得混合物剧烈搅拌2小时。在搅拌下将该反应在水/乙酸乙酯中终止。将所得两相体系过滤并分离各层。随后将水层用乙酸乙酯萃取。将合并的有机相用盐水洗涤,用Na2SO4干燥并浓缩而得到5.15g标题化合物。GCMSm/e(M+)=256
向无水甲苯中的6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(5.1g,19.91mmol)中滴加在无水甲苯中的双光气(2.64ml,21.90mmol)。将所得混合物在回流下搅拌过夜。将该混合物浓缩,用甲苯捕集并直接用于下一步中。
嗪-6-基)-1H-嘧啶-2,4-二酮
在5℃和N2下将(E)-3-氨基-4,4,4-三氟丁-2-烯酸乙酯(4.24g,23.2mmol)的溶液滴加到氢化钠(1.01g55%在矿物油中的悬浮液,23.2mmol)在无水DMF中的搅拌溶液中。将该浅黄色悬浮液搅拌1小时,同时使反应混合物温热至室温。在该段时间滴加2,2,7-三氟-6-异氰酸酯基-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(6.54g,23.2mmol)在甲苯中的溶液,然后在氮气下将该混合物在80℃下过夜加热。由于LC/MS显示该反应不完全,因此继续在100℃下再加热3小时,然后真空浓缩该浅褐色溶液。将深色残余物分配在乙酸乙酯和氯化铵水溶液之间,并用额外的乙酸乙酯萃取水相。将合并的有机级分用盐水洗涤并在Na2SO4上干燥。过滤并蒸发溶剂得到10.68g粗褐色油。通过柱层析(EtOAc∶庚烷,20-60%)将其提纯而得到三个级分,其中所需产物为主组分(以酮基和烯醇互变异构体的混合物存在)。将这三种级分合并并通过柱层析进一步提纯,其中使用二异丙醚洗脱,以灰白色蓬松固体得到产物(3.0g)(纯度根据NMR为94%,约20%以烯醇互变异构体存在)。
主要(酮基)互变异构体的1H-NMR(DMSO):2.50(s,1H),4.78(s,2H),6.47(s,1H),7.72(m,2H),12.86(br,1H)。在H/D交换(使用D2O)时在12.86ppm下的宽峰消失。
经由氨基甲酸酯制备最后中间体方案6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-1H-嘧啶-2,4-二酮的替代程序:
甲酸乙酯
将6-氨基-2,2,7-三氟-4-(丙-2-炔基)-2H-苯并[b][1,4]嗪-3(4H)-酮(2.0g,7.8mmol)和氯甲酸乙酯(1.14g,10.5mmol)在无水甲苯中的混合物加热至回流并保持2小时。将该混合物蒸发至干,得到褐色固体。柱层析(二氧化硅,EtOAc∶庚烷,1∶3)得到产物(1.04g),将其在不进一步提纯下用于下一步骤1.8a中。
1.8a:6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并
将氢化钠(24.4mg,0.61mmol)加入(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)氨基甲酸乙酯(100mg,0.31mmol)在DMF中的搅拌溶液中。将该混合物加热至120℃并保持18小时。通过LC/MS分析证实形成所需产物(1.932分钟的保留时间和质谱与经由异氰酸酯制备的可靠样品相同。
1.9:1-甲基-6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并
在室温下将硫酸二甲酯(0.36g,2.86mmol)在二氯甲烷中的溶液加入6-三氟甲基-3-(2,2,7-三氟-3-氧代-4-丙-2-炔基-3,4-二氢-2H-苯并[1,4]嗪-6-基)-1H-嘧啶-2,4-二酮(1.0g,2.4mmol)和二异丙基乙基胺(0.62g,4.8mmol)在二氯甲烷中的搅拌溶液中。将所得反应混合物加热至50℃(外部温度)。在该温度下1小时之后,薄层色谱法(TLC)分析显示完全转化。将该混合物用二氯甲烷稀释并用1NHCl和饱和碳酸氢盐溶液洗涤。将有机相干燥(Na2SO4)并蒸发至干,以褐色油得到粗产物。柱层析(EtOAc∶庚烷,10-45%)得到白色泡沫。这由制备型液相色谱法进一步提纯而得到两个级分:级分1(229mg,纯度为93%)以及级分2(264mg,纯度为90%)。级分1的1H-NMR(DMSO):2.36(s,1H),3.57(s,3H),4.74(s,2H),6.39(s,1H),7.1-7.2(m,2H)。
应用实施例
式I的尿嘧啶的除草活性由下列温室试验证实:
所用培养容器为含有含约3.0%腐殖土的壤质砂作为底物的塑料花盆。对每一品种单独播种测试植物的种子。
对于出苗前处理,直接在播种之后借助细分布喷嘴施用悬浮或乳化于水中的活性成分。温和灌溉容器以促进发芽和生长,然后用透明塑料罩覆盖,直到植物生根。该覆盖导致测试植物均匀发芽,除非被活性成分损坏。
对于出苗后处理,首先使测试植物生长到3-15cm的高度,这取决于植物习性,仅在此时用悬浮或乳化于水中的活性成分处理。为此,将测试植物直接播种并在相同容器中生长,或者首先使它们作为秧苗单独生长并在处理之前几天移植到测试容器中。
取决于品种,将植物保持在10-25℃或20-35℃。测试期为2-4周。在此期间照料植物并评价它们对各处理的响应。
使用0-100的评分进行评价。100表示没有植物出苗,或者至少地面上部分完全受损,而0表示没有损害,或者生长过程正常。对良好的除草活性给予至少70的分值,而对非常好的除草活性给予至少85的分值。
用于温室试验中的植物属于下列品种:
Bayer代码 | 学名 | 通用名 |
ABUTH | Abutilon theophrasti | 苘麻 |
AMARE | Amaranthus retroflexus | 马齿苋 |
BRADE | 弯臂粟(Brachiaria deflexa) | -- |
BRAPL | Brachiaria plantaginea | 四生臂形草 |
CHEAL | Chenopodium album | 藜 |
COMBE | Commenline benghalensis | 圆叶鸭跖草 |
Bayer代码 | 学名 | 通用名 |
DIGSA | Digitaria sanguinales | 马唐 |
ELEIN | Eleusine indica | 牛筋草 |
ERICA | Erigeron canadensis | 加拿大飞蓬 |
PHBPU | Pharbitis purpurea | 圆叶牵牛 |
SETFA | Setaria faberi | 大狗尾草 |
SETVI | Setaria viridis | 狗尾草 |
SOLNI | Solanum nigrum | 龙葵 |
在6.25g/ha的施用率下,通过出苗后方法施用的化合物Ia48对苘麻、马齿苋、藜和圆叶牵牛显示出非常好的除草活性。
在6.25g/ha的施用率下,通过出苗前方法施用的化合物Ia48对马齿苋、加拿大飞蓬和龙葵显示出非常好的除草活性。
表2:通过出苗后方法施用的混合物1.54的协同增效除草作用
表3:通过出苗后方法施用的混合物1.93的协同增效除草作用
表4:通过出苗后方法施用的混合物1.98的协同增效除草作用
表5:通过出苗后方法施用的混合物1.118的协同增效除草作用
表6:通过出苗后方法施用的混合物26.98的协同增效除草作用
表7:本发明实施例1和由WO90/15057已知的实施例39在0.025kg/ha的施用率下在处理后8天的出苗前除草活性对比(温室)
测试数据清楚地表明在苯并[1,4]嗪环的2位中引入卤原子导致与由WO90/15057已知的实施例39所实现的相比的优异除草活性,其中在后者中苯并[1,4]嗪环在2位未被取代。
Claims (11)
1.式I的尿嘧啶:
其中
R1为卤素;
R2为C1-C6烷基、C3-C6链烯基或C3-C6炔基;
R3为卤素;
R4为卤素;
R5为C1-C6烷基;
R6为C1-C6卤代烷基;
R7为氢;
X为O;和
Y为O;
或其可农用盐。
2.如权利要求1所要求的式I的尿嘧啶,其中R4为F。
3.如权利要求1或2所要求的式I的尿嘧啶,其中R2为C3-C6炔基。
4.一种制备根据权利要求1的式I的尿嘧啶的方法,其中使式II的异氰酸酯:
其中变量R1、R2、R3、R4、X和Y如权利要求1所定义,
与式III的烯胺反应:
其中变量R5、R6和R7如权利要求1所定义,以及
L1为C1-C6烷氧基、C1-C6卤代烷氧基、C1-C4烷氧基-C2-C4烷氧基、C1-C4烷硫基-C2-C4烷氧基、C2-C6链烯氧基、C2-C6卤代链烯氧基、C3-C6炔氧基、C3-C6卤代炔氧基、C3-C6环烷氧基、C1-C6氰基烷氧基或苄氧基,其本身可以在苯基环上部分或完全被卤代和/或可以被1-3个选自如下的基团取代:氰基、硝基、C1-C4烷基、C1-C4烷氧基和C1-C4烷硫基。
5.式V的氨基甲酸酯:
其中
R1为卤素;
R2为C1-C6烷基、C3-C6链烯基或C3-C6炔基;
R3为卤素;
R4为卤素;
X为O;
Y为O;以及
L2为C1-C6烷氧基、C1-C6烷硫基或芳氧基,其中芳基结构部分本身可以部分或完全被卤代和/或可以被1-3个选自氰基、硝基、C1-C4烷基、C1-C4烷氧基和C1-C4烷硫基的基团取代,
其中所述芳氧基的芳基结构部分为具有6-14个环成员的单至三核芳族碳环。
6.根据权利要求5的氨基甲酸酯,其为下式化合物:
7.一种除草组合物,包含除草活性量的至少一种如权利要求1-3中任一项所要求的式I的尿嘧啶和至少一种选自除草剂B和/或安全剂C的其他活性化合物,
其中所述除草剂B选自b1)-b15)类除草剂:
b1)类脂生物合成抑制剂;
b2)乙酰乳酸合成酶抑制剂;
b3)光合成抑制剂;
b4)原卟啉原-IX氧化酶抑制剂,
b5)漂白剂除草剂;
b6)烯醇丙酮酰莽草酸3-磷酸合成酶抑制剂;
b7)谷氨酰胺合成酶抑制剂;
b8)7,8-二氢蝶酸合成酶抑制剂;
b9)有丝***抑制剂;
b10)非常长链脂肪酸合成抑制剂;
b11)纤维素生物合成抑制剂;
b12)去偶剂除草剂;
b13)植物生长素除草剂;
b14)植物生长素输送抑制剂;和
b15)选自溴丁酰草胺、chlorflurenol、chlorflurenol-methyl、环庚草醚、苄草隆、茅草枯、棉隆、difenzoquat、difenzoquat-metilsulfate、噻节因、甲胂钠、香草隆、敌草腈及其盐、乙苯酰草、flamprop、flamprop-isopropyl、甲氟燕灵、强氟燕灵、麦草伏、flurenol、flurenol-butyl、调嘧醇、fosamine、fosamine-ammonium、茚草酮、indaziflam、抑芽丹、氟草磺、威百亩、叠氮甲烷、溴甲烷、苯丙隆、碘甲烷、甲胂一钠、油酸、氯嗪草、壬酸、稗草畏、灭藻醌、苯氧丙胺津、灭草环和6-氯-3-(2-环丙基-6-甲基苯氧基)-4-哒嗪醇及其盐和酯的其他除草剂,
所述安全剂C选自:解草酮、喹氧乙酸、抑害腈、cyprosulfamide、抑害胺、dicyclonon、dietholate、解草唑、解草啶、解草安、肟草安、解草呋、双苯唑酸、吡咯二酸、mephenate、萘二甲酸酐、解草腈,4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷和2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷。
8.根据权利要求7的组合物,其包含至少两种选自除草剂B和/或安全剂C的其他活性化合物。
9.一种除草组合物,包含除草活性量的至少一种如权利要求1-3中任一项所要求的式I的尿嘧啶或如权利要求7或8所要求的除草组合物和至少一种惰性液体和/或固体载体,任选地至少一种表面活性物质。
10.一种制备除草活性组合物的方法,包括将除草活性量的至少一种如权利要求1-3中任一项所要求的式I的尿嘧啶或如权利要求7或8所要求的除草组合物和至少一种惰性液体和/或固体载体以及任选地至少一种表面活性物质混合。
11.一种防治不希望的植物生长的方法,包括使除草活性量的至少一种如权利要求1-3中任一项所要求的式I的尿嘧啶或如权利要求7或8所要求的除草组合物作用于植物、其环境或种子上。
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UY33030A (es) | 2011-05-31 |
AR079027A1 (es) | 2011-12-21 |
JP2013510810A (ja) | 2013-03-28 |
EP2499136A1 (en) | 2012-09-19 |
BR112012011059B1 (pt) | 2021-02-17 |
BR112012011059B8 (pt) | 2021-05-04 |
EP2499136B1 (en) | 2013-12-04 |
BR112012011059A2 (pt) | 2020-09-15 |
US20120231952A1 (en) | 2012-09-13 |
US8481723B2 (en) | 2013-07-09 |
TW201124407A (en) | 2011-07-16 |
WO2011057935A1 (en) | 2011-05-19 |
ES2440940T3 (es) | 2014-01-31 |
US8748348B2 (en) | 2014-06-10 |
US20130345054A1 (en) | 2013-12-26 |
IL219718A (en) | 2015-11-30 |
DK2499136T3 (en) | 2014-03-03 |
CN102762552A (zh) | 2012-10-31 |
MX2012005501A (es) | 2012-07-10 |
IL219718A0 (en) | 2012-07-31 |
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