CN117794928A - 取代的1,2,4-噻二唑基烟酰胺、其盐或n-氧化物及其作为除草活性物质的用途 - Google Patents
取代的1,2,4-噻二唑基烟酰胺、其盐或n-氧化物及其作为除草活性物质的用途 Download PDFInfo
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- CN117794928A CN117794928A CN202280054477.0A CN202280054477A CN117794928A CN 117794928 A CN117794928 A CN 117794928A CN 202280054477 A CN202280054477 A CN 202280054477A CN 117794928 A CN117794928 A CN 117794928A
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- Prior art keywords
- methyl
- group
- halogen
- alkyl
- represents hydrogen
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- -1 1,2, 4-thiadiazolyl nicotinamide Chemical class 0.000 title claims abstract description 159
- 150000003839 salts Chemical class 0.000 title claims abstract description 68
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- 239000013543 active substance Substances 0.000 title claims description 5
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- 150000001875 compounds Chemical class 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 69
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 238000000034 method Methods 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
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- 239000000126 substance Substances 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 230000001276 controlling effect Effects 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
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- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
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- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
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- 239000011734 sodium Substances 0.000 description 34
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- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 13
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- 238000012360 testing method Methods 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
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- 235000019713 millet Nutrition 0.000 description 9
- 108090000623 proteins and genes Proteins 0.000 description 9
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
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- 125000003342 alkenyl group Chemical group 0.000 description 8
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- 235000013339 cereals Nutrition 0.000 description 8
- HLZCHRAMVPCKDU-UHFFFAOYSA-M dicamba-sodium Chemical compound [Na+].COC1=C(Cl)C=CC(Cl)=C1C([O-])=O HLZCHRAMVPCKDU-UHFFFAOYSA-M 0.000 description 8
- 239000011591 potassium Substances 0.000 description 8
- 229910052700 potassium Inorganic materials 0.000 description 8
- 229960003975 potassium Drugs 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 239000005499 Clomazone Substances 0.000 description 7
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
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- 238000003818 flash chromatography Methods 0.000 description 7
- 125000004438 haloalkoxy group Chemical group 0.000 description 7
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 7
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- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- YNWVFADWVLCOPU-MAUPQMMJSA-N uniconazole P Chemical compound C1=NC=NN1/C([C@@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MAUPQMMJSA-N 0.000 description 1
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Abstract
本发明涉及通式(I)的取代的1,2,4‑噻二唑基烟酰胺及其盐或N‑氧化物,
Description
本发明涉及除草剂和/或植物生长调节剂的技术领域。特别地,本发明主要涉及取代的1,2,4-噻二唑基烟酰胺和包含所述取代的1,2,4-噻二唑基烟酰胺的组合物。
此外,本发明还涉及所述取代的1,2,4-噻二唑基烟酰胺的制备方法及其作为除草剂和/或植物生长调节剂的用途。
在它们的应用中,迄今已知的用于选择性防治有用植物的作物中的有害植物的作物保护剂或用于防治不想要的植被的活性化合物有时具有以下缺点:(a)它们对特定的有害植物没有或没有足够的除草活性,(b)可用活性化合物防治的有害植物的谱不够宽,(c)其在有用植物的作物中的选择性太低,和/或(d)它们在毒理学上具有不利的性质。
此外,可用作许多有用植物的植物生长调节剂的一些活性化合物在其他有用植物中导致不想要的采收物产量的减少,或与作物植物不相容,或仅在窄的施用率范围内。此外,由于难以获得的前体和试剂,或它们仅具有不足的化学稳定性,一些已知的活性化合物不能以工业规模经济地制备。
现有技术公开了若干表现出有益性质和用途的取代的1,2,4-噻二唑。专利US4416683、US4515625、US4636243和US4801718涉及杂环取代的N-苯甲酰胺及其作为除草剂防治不想要植物的用途。
US4343945记载了三氯甲基取代的1,2,4-噻二唑可用作除草剂、杀菌剂和杀虫剂。
此外,DE2154852公开了5-取代的氨基-3-异丙基-1,2,4-噻二唑是高效农药。
此外,DE19601139涉及酰化5-氨基-1,2,4-噻二唑的制备及其作为农药的用途。
若干文件(WO01/36415、WO01/40206、WO01/40223和WO01/46165)记载了取代的1,2,4-噻二唑也适用于防治各种害虫。
WO2017/005717和WO2018/108791显示了,芳基和杂芳基取代的1,2,4-噻二唑对防治有用植物的作物中不想要的昆虫很有效果。
然而,目前尚未报道取代的带有邻烷基或邻卤代烷基取代基的1,2,4-噻二唑基烟酰胺、其盐或N-氧化物作为除草活性化合物。出乎意料地,现已发现,取代的带有邻烷基或邻卤代烷基取代基的1,2,4-噻二唑基烟酰胺、其盐或N-氧化物特别适合作为除草剂。
在它们的应用中,迄今已知的用于防治有用植物的作物中的有害植物的除草剂或用于防治不想要的植被的除草剂有时具有以下缺点:(a)它们对特定的有害植物没有或没有足够的除草活性,(b)可用活性化合物防治的有害植物的谱不够宽,和/或(c)除草剂在作物植物中的选择性及其与作物植物的相容性太低,由此导致不想要的损害和/或不想要的作物采收物产量的减少。
因此,仍然需要替代性除草剂,特别是在低施用率下有用的和/或与作物植物有良好相容性的高活性除草剂,用于在植物作物中的选择性施用或在非耕地上的使用。此外,还需要提供可以有利方式用作除草剂或植物生长调节剂的替代性化学活性化合物。
因此,本发明的目的是提供具有除草活性的化合物,其即使在相对低的施用率下也能对经济上重要的有害植物产生有高的功效,并且可以在一种或多种作物植物中选择性地使用。
现已发现以下通式(I)的化合物、其盐或N-氧化物满足所述目的。
因此,本发明提供通式(I)的取代的1,2,4-噻二唑基烟酰胺、其盐或N-氧化物
其中
W 表示氧或硫,
R1 表示氢、卤素、氰基、(C1-C3)-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)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷硫基、(C1-C4)-卤代烷基亚磺酰基或(C1-C4)-卤代烷基磺酰基,
R2 表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3 表示氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基,
R4 表示氢、卤素、氰基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基,
R5 表示氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C3-C6)-卤代环烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基。
通式(I)的化合物可通过将合适的无机酸或有机酸加成至碱性基团上而形成盐,所述无机酸或有机酸为例如无机酸,如HCl、HBr、H2SO4、H3PO4或HNO3;或有机酸如羧酸,例如甲酸、乙酸、丙酸、草酸、乳酸或水杨酸,或磺酸,例如对甲苯磺酸;所述碱性基团为例如氨基、烷基氨基、二烷基氨基、哌啶基、吗啉基或吡啶基。在这种情况中,这些盐将包含酸的共轭碱作为阴离子。去质子化形式的合适的取代基(例如磺酸,特别是磺酰胺,或羧酸)能够与本身可被质子化的基团(例如氨基)形成内盐。通过碱作用于通式(I)的化合物也可形成盐。合适的碱为例如有机胺,如三烷基胺、吗啉、哌啶和吡啶,以及铵、碱金属或碱土金属的氢氧化物、碳酸盐和碳酸氢盐,特别是氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和碳酸氢钾。这些盐为这样的化合物,其中酸性氢被农业上适合的阳离子替代,例如金属盐,特别是碱金属盐或碱土金属盐,尤其是钠盐和钾盐,或者铵盐、具有有机胺的盐或季铵盐,例如具有式[NRaRbRcRd]+的阳离子的盐,其中Ra至Rd各自独立地为有机基团,特别是烷基、芳基、芳基烷基或烷基芳基。同样合适的为烷基锍盐和烷基氧化锍盐,例如(C1-C4)-三烷基锍盐和(C1-C4)-三烷基氧化锍盐。
取决于外部条件如pH、溶剂和温度,本发明通式(I)的取代的1,2,4-噻二唑基烟酰胺可以各种互变异构体结构存在,它们均被通式(I)所涵盖。
根据本发明使用的式(I)的化合物、其盐和N-氧化物在下文中也称为“通式(I)的化合物”。
本发明优选提供这样的通式(I)的化合物、其盐和N-氧化物,其中
W 表示氧或硫,
R1 表示氢、卤素、(C1-C3)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基或(C1-C4)-卤代烷硫基,
R2 表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3 表示氢、卤素、(C1-C4)-烷基或(C1-C4)-卤代烷基,
R4 表示氢、卤素或(C1-C4)-卤代烷基,
R5 表示氢、卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基。
本发明特别提供这样的通式(I)的化合物、其盐和N-氧化物,其中
W 表示氧或硫,优选氧,
R1 表示氢、卤素、(C1-C3)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-烷硫基,
R2 表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3 表示氢,
R4 表示氢或卤素,
R5 表示氢、卤素、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基。
本发明更特别提供这样的通式(I)的化合物、其盐和N-氧化物,其中
W 表示氧,
R1 表示氢、氯、溴、甲基、乙基、三氟甲基、三氯甲基、甲氧基或甲基磺酰基(methylsulfanyl),
R2 表示甲基、乙基、异丙基、二氟甲基或三氟甲基,
R3 表示氢,
R4 表示氢、氟或氯,
R5 表示氢、氟、氯、溴、二氟甲基、环丙基或甲氧基。
本发明尤其提供这样的通式(I)的化合物、其盐和N-氧化物,其中
W 表示氧,
R1 表示氢、氯、溴、甲基或三氟甲基,
R2 表示甲基、乙基、异丙基或三氟甲基,
R3 表示氢,
R4 表示氢、氟或氯,
R5 表示氢、氟、氯、溴、甲氧基或环丙基。
上文概述性列出的或在优选范围内列出的基团定义适用于通式(I)的最终产物和相应的在每种情况下制备所需的起始物质或中间体。这些基团定义可根据需要彼此结合,即,包括给出的优选范围之间的结合。
主要由于除草活性更高、选择性更好和/或生产性更好的原因,根据本发明的上述通式(I)的化合物和/或其盐和N-氧化物或根据本发明的用途是特别令人关注的,其中单个基团具有已指定或下文指定的优选含义之一,或特别是其中以组合形式出现的一个或多个已指定或下文指定的优选含义的那些。
关于本发明的化合物,将阐述上文和进一步在下文中使用的术语。它们是本领域技术人员所常见的且特别具有下文所述的定义。
除非另有定义,化学基团的名称一般应这样理解,通过最后提及的结构元素与分子的骨架或剩余部分相连接,即,例如在(C2-C8)-烯氧基的情况下,通过氧原子连接,在(C1-C8)-烷氧基-(C1-C4)-烷基或(C1-C8)-烷氧基羰基-(C1-C8)-烷基的情况下,各自通过烷基的碳原子连接。
根据本发明,“烷基磺酰基”──单独或作为化学基团的一部分──是指直链或支链的烷基磺酰基,其优选具有1至8个或1至6个碳原子,例如(但不限于)(C1-C6)-烷基磺酰基,如甲基磺酰基、乙基磺酰基、丙基磺酰基、1-甲基乙基磺酰基、丁基磺酰基、1-甲基丙基磺酰基、2-甲基丙基磺酰基、1,1-二甲基乙基磺酰基、戊基磺酰基、1-甲基丁基磺酰基、2-甲基丁基磺酰基、3-甲基丁基磺酰基、1,1-二甲基丙基磺酰基、1,2-二甲基丙基磺酰基、2,2-二甲基丙基磺酰基、1-乙基丙基磺酰基、己基磺酰基、1-甲基戊基磺酰基、2-甲基戊基磺酰基、3-甲基戊基磺酰基、4-甲基戊基磺酰基、1,1-二甲基丁基磺酰基、1,2-二甲基丁基磺酰基、1,3-二甲基丁基磺酰基、2,2-二甲基丁基磺酰基、2,3-二甲基丁基磺酰基、3,3-二甲基丁基磺酰基、1-乙基丁基磺酰基、2-乙基丁基磺酰基、1,1,2-三甲基丙基磺酰基、1,2,2-三甲基丙基磺酰基、1-乙基-1-甲基丙基磺酰基和1-乙基-2-甲基丙基磺酰基。
根据本发明,“烷硫基”──单独或作为化学基团的一部分──表示直链或支链的S-烷基,其优选具有1至8个或1至6个碳原子,如(C1-C10)-、(C1-C6)-或(C1-C4)-烷硫基,例如(但不限于)(C1-C6)-烷硫基,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、1,1-二甲基乙硫基、戊硫基、1-甲基丁硫基、2-甲基丁硫基、3-甲基丁硫基、1,1-二甲基丙硫基、1,2-二甲基丙硫基、2,2-二甲基丙硫基、1-乙基丙硫基、己硫基、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。
根据本发明,除非另有定义,“烷基亚磺酰基(烷基-S(=O)-)”表示通过-S(=O)-与骨架相连的烷基,例如(C1-C10)-、(C1-C6)-或(C1-C4)-烷基亚磺酰基,例如(但不限于)(C1-C6)-烷基亚磺酰基,如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、1-甲基乙基亚磺酰基、丁基亚磺酰基、1-甲基丙基亚磺酰基、2-甲基丙基亚磺酰基、1,1-二甲基乙基亚磺酰基、戊基亚磺酰基、1-甲基丁基亚磺酰基、2-甲基丁基亚磺酰基、3-甲基丁基亚磺酰基、1,1-二甲基丙基亚磺酰基、1,2-二甲基丙基亚磺酰基、2,2-二甲基丙基亚磺酰基、1-乙基丙基亚磺酰基、己基亚磺酰基、1-甲基戊基亚磺酰基、2-甲基戊基亚磺酰基、3-甲基戊基亚磺酰基、4-甲基戊基亚磺酰基、1,1-二甲基丁基亚磺酰基、1,2-二甲基丁基亚磺酰基、1,3-二甲基丁基亚磺酰基、2,2-二甲基丁基亚磺酰基、2,3-二甲基丁基亚磺酰基、3,3-二甲基丁基亚磺酰基、1-乙基丁基亚磺酰基、2-乙基丁基亚磺酰基、1,1,2-三甲基丙基亚磺酰基、1,2,2-三甲基丙基亚磺酰基、1-乙基-1-甲基丙基亚磺酰基和1-乙基-2-甲基丙基亚磺酰基。
“烷氧基”表示通过氧原子键合的烷基基团,例如(但不限于)(C1-C6)-烷氧基,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、1,1-二甲基乙氧基、戊氧基、1-甲基丁氧基、2-甲基丁氧基、3-甲基丁氧基、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。烯氧基表示通过氧原子连接的烯基,炔氧基表示通过氧原子连接的炔基,如(C2-C10)-、(C2-C6)-或(C2-C4)-烯氧基和(C3-C10)-、(C3-C6)-或(C3-C4)-炔氧基。
术语“卤素”是指例如氟、氯、溴或碘。如果该术语用于基团,则“卤素”是指例如氟、氯、溴或碘原子。
根据本发明,“烷基”表示直链或支链的开链的饱和烃基,其任选地被单取代或多取代,在后一种情况下被称为“取代的烷基”。优选的取代基为卤素原子、烷氧基、卤代烷氧基、氰基、烷硫基、卤代烷硫基、氨基或硝基,特别优选甲氧基、甲基、氟烷基、氰基、硝基、氟、氯、溴或碘。
前缀“二”包括相同或不同烷基基团的组合,例如二甲基或甲基(乙基)或乙基(甲基)。
“卤代烷基”、“卤代烯基”和“卤代炔基”分别表示被相同或不同卤素原子部分或完全取代的烷基、烯基和炔基,例如单卤代烷基,如CH2CH2Cl、CH2CH2Br、CHClCH3、CH2Cl、CH2F;全卤代烷基,如CCl3、CClF2、CFCl2、CF2CClF2、CF2CClFCF3;多卤代烷基,如CH2CHFCl、CF2CClFH、CF2CBrFH、CH2CF3,术语全卤代烷基也涵盖术语全氟代烷基。
“卤代烷氧基”为例如OCF3、OCHF2、OCH2F、OCF2CF3、OCH2CF3和OCH2CH2Cl;这相应地适用于卤代烯基和其他卤素取代的基团。
根据所述碳原子范围,本文中作为例子提及的表述“(C1-C4)-烷基”为具有1至4个碳原子的直链或支链的烷基的简要记法,即涵盖甲基、乙基、1-丙基、2-丙基、1-丁基、2-丁基、2-甲基丙基或叔丁基。具有更大指定的碳原子范围的一般烷基基团(例如“C1-C6烷基”)还相应地涵盖具有更大碳原子数的直链或支链的烷基,即根据实例还涵盖具有5和6个碳原子的烷基。
除非另有说明,在不饱和基团的情况下,在烃基如烷基、烯基和炔基基团(包括复合基团中的)的情况下,优选低级碳骨架,其例如具有1至6个碳原子,或具有2至6个碳原子。烷基基团(包括复合基团如烷氧基、卤代烷基等中的烷基基团)为例如甲基、乙基、正丙基或异丙基、正丁基、异丁基、叔丁基或2-丁基、戊基、己基(如正己基、异己基和1,3-二甲基丁基)、庚基(如正庚基、1-甲基己基和1,4-二甲基戊基);烯基和炔基被定义为与烷基相对应的可能的不饱和基团,其中存在至少一个双键或三键。优选具有一个双键或三键的基团。
术语“环烷基”表示优选具有3-8个环碳原子的碳环饱和环体系,例如环丙基、环丁基、环戊基或环己基,其任选具有其他取代,优选被以下基团取代:氢、烷基、烷氧基、氰基、硝基、烷硫基、卤代烷硫基、卤素、烯基、炔基、卤代烷基、氨基、烷基氨基、二烷基氨基、烷氧基羰基、羟基羰基、芳基烷氧基羰基、氨基羰基、烷基氨基羰基、环烷基氨基羰基。在任选取代的环烷基的情况下,包括具有取代基的环体系,也包括在环烷基上带有双键的取代基,如亚烷基基团如亚甲基。在任选取代的环烷基的情况下,还包括多环脂族体系,例如双环[1.1.0]丁-1-基、双环[1.1.0]丁-2-基、双环[2.1.0]戊-1-基、双环[1.1.1]戊-1-基、双环[2.1.0]戊-2-基、双环[2.1.0]戊-5-基、双环[2.1.1]己基、双环[2.2.1]庚-2-基、双环[2.2.2]辛-2-基、双环[3.2.1]辛-2-基、双环[3.2.2]壬-2-基、金刚烷-1-基和金刚烷-2-基,以及如1,1'-双(环丙基)-1-基、1,1'-双(环丙基)-2-基之类的体系。术语“(C3-C7)-环烷基”是具有3至7个碳原子的环烷基的简要记法,对应于指定碳原子范围。
在取代的环烷基的情况下,还包括螺环脂族体系,例如螺[2.2]戊-1-基、螺[2.3]己-1-基、螺[2.3]己-4-基、3-螺[2.3]己-5-基、螺[3.3]庚-1-基、螺[3.3]庚-2-基。
根据本发明,“卤代烷硫基”──其本身或作为化学基团的一部分──表示直链或支链的S-卤代烷基,其优选具有1至8个,或具有1至6个碳原子,如(C1-C8)-、(C1-C6)-或(C1-C4)-卤代烷硫基,例如(但不限于)三氟甲硫基、五氟乙硫基、二氟甲基、2,2-二氟乙-1-基硫、2,2,2-二氟乙-1-基硫、3,3,3-丙-1-基硫。
“卤代环烷基”表示被相同或不同卤素原子(如F、Cl和Br)或卤代烷基(如三氟甲基或二氟甲基)部分或完全取代的环烷基,例如1-氟环丙-1-基、2-氟环丙-1-基、2,2-二氟环丙-1-基、1-氟环丁-1-基、1-三氟甲基环丙-1-基、2-三氟甲基环丙-1-基、1-氯环丙-1-基、2-氯环丙-1-基、2,2-二氯环丙-1-基、3,3-二氟环丁基。
如果化合物可以通过氢迁移形成互变异构体,所述互变异构体的结构未被通式(I)形式上涵盖,尽管如此,这些互变异构体仍被本发明通式(I)的化合物的定义所涵盖,除非正在考虑特定的互变异构体。例如,许多羰基化合物可能以酮的形式和烯醇的形式存在,通式(I)的化合物的定义涵盖这两种形式。
取决于取代基的性质和它们连接的方式,通式(I)的化合物可以作为立体异构体存在。通式(I)涵盖由其特定三维形式定义的所有可能的立体异构体,例如对映异构体、非对映异构体、Z和E异构体。例如,如果存在一个或多个烯基,则可能出现非对映异构体(Z和E异构体)。例如,如果存在一个或多个不对称碳原子,则可能出现对映异构体和非对映异构体。立体异构体可以通过常规分离方法从在制备中获得的混合物中获得。色谱分离可以在分析规模上进行以发现对映体过量或非对映体过量,或者在制备规模上进行以产生用于生物测试的测试样品。同样可以通过在使用光学活性起始材料和/或助剂的情况下使用立体选择性反应来选择性地制备立体异构体。因此,本发明还涉及被通式(I)所涵盖但未以其特定的立体异构形式示出的所有立体异构体,及其混合物。
如果化合物以固体形式获得,则纯化也可以通过重结晶或消化(digestion)进行。如果通过下文描述的路线不能以令人满意的方式获得通式(I)的各个化合物,则它们可以通过通式(I)的其它化合物的衍生来制备。
合适的分离方法、纯化方法和分离通式(I)的化合物的立体异构体的方法是本领域技术人员通常从类似案例中知晓的方法,例如通过物理方法,例如结晶,色谱方法、特别是柱色谱法和HPLC(高压液相色谱),蒸馏(任选地在减压下),萃取和其他方法,剩余的任何混合物通常皆可通过色谱分离法(例如在手性固体相上)分离。适合用于制备量或工业规模的是如结晶之类的方法,例如非对映体盐的结晶,其可使用光学活性酸以及──如果合适,假如存在酸性基团──使用光学活性碱而从非对映体混合物中获得。
通式(1)的取代的1,2,4-噻二唑基烟酰胺的合成:
可使用已知的方法制备本发明通式(I)的取代的1,2,4-噻二唑基烟酰胺。所使用和研究的合成路线是从市售的或易于合成的取代的1,2,4-噻二唑,或其盐(例如盐酸盐或二盐酸盐)和取代的羧酸开始的。在下面的方案中,除非给出示例性但非限制性的定义,否则通式(I)的基团R1、R2、R3、R4、R5和W具有上文定义的含义。通式(I)的取代的1,2,4-噻二唑基烟酰胺的第一合成路线经由任选取代的氨基噻二唑(II)或其盐和任选取代的羧酸(III)开始(方案1)。为此,在合适的偶联剂(例如亚硫酰氯)和合适的碱(例如1-甲基-1H-咪唑)存在下,取代的氨基噻二唑与取代的羧酸反应,得到目标1,2,4-噻二唑基烟酰胺(I)(cf.US2019/0233382)。或者,可以使用氨基噻二唑的盐,与在反应混合物中生成的游离胺。存在可用于实现该反应的过量酰胺偶联剂和碱(参考Chem.Soc.Rev.,2009,38,606-631)。其他合适的酰胺偶联剂包括但不限于草酰氯、T3P(丙烷膦酸酐)、DIC(1,3-二异丙基碳二亚胺)和HATU(1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓3-氧化物六氟磷酸盐),并且其他合适的碱包括但不限于三乙胺、DIPEA(N,N-二异丙基乙胺)和吡啶。在下文的方案1中,R1、R2、R3、R4和R5具有上文定义的含义,W=氧。
或者,通式(I)的取代的1,2,4-噻二唑基烟酰胺的合成可以通过任选取代的酰基氯(IV)与任选取代的1,2,4-噻二唑(II)的直接酰胺偶联来完成(方案2)。按照该方法,用氯化试剂(例如草酰氯与DMF=N,N-二甲基甲酰胺的催化剂量)从相应的羧酸(III)预先制备的酰基氯(IV)在碱(例如三乙胺)和合适的溶剂(例如THF=四氢呋喃)的存在下与1,2,4-噻二唑(II)反应,得到取代的1,2,4-噻二唑基烟酰胺(I)。多种试剂可用于这种转化(参考Chem.Soc.Rev.,2009,38,606-631)以及使用适当的催化剂(例如DMAP=4-二甲氨基吡啶)。在下文的方案2中,R1、R2、R3、R4和R5具有上文定义的含义,W=氧。
此外,通式(I)的取代的1,2,4-噻二唑基烟酰胺的合成还可以通过取代的1,2,4-噻二唑(II)与任选取代的酯(V)的直接酰胺偶联来实现(方案3)。对于这些反应,需要适当的试剂(例如三甲基铝)和合适的溶剂(例如二氯甲烷或甲苯)来进行(参考Chem.Commun.,2008,1100-1102)。Commun。农业学报,2008,1100-1102)。这种转化也可以用文献(Tetrahedron Lett.,2006,47,5767-5769)中已知的各种其他试剂来完成。在下文的方案3中,R1、R2、R3、R4和R5具有上文定义的含义,W=氧。
通式(I)的取代的1,2,4-噻二唑基烟酰胺的合成还可以通过独立制备任选取代的羧酸,然后与取代的1,2,4-噻二唑进行关键的酰胺偶联来完成。按照该方法(方案4),在合适的添加剂(例如BF3.OEt2)和适当的溶剂(例如THF=四氢呋喃)存在下,用有机金属试剂(例如i-PrMgCl·LiCl)处理酯(VI),得到取代的酯(VII)(参考J.Am.Chem.Soc.,2013,135,4958-4961)。然后用合适的碱(例如氢氧化钠)水解酯(VII)得到羧酸(VIII),羧酸(VIII)与1,2,4-噻二唑(II)用前述的方法(方案1、2和3)反应得到通式(I)的目标1,2,4-噻二唑基烟酰胺。在下文的方案4中,R1、R2、R3、R4和R5具有上文定义的含义。异丙基取代的羧酸(VIII)的合成以实例的方式而非限制的方式示出。
下面给出了所选的本发明的通式(I)的化合物的详细合成实施例。所提及的实施例编号对应于方案1至3和下表1中的编号方案。所报告的以下部分中描述的化学实施例的1H NMR谱数据在Bruker仪器上在600MHz、400MHz或300MHz下使用CDCl3或d6-DMSO作为溶剂使用四甲基硅烷(δ=0.00ppm)作为内标获得。所列信号具有下面给出的含义:br=宽峰;s=单重峰,d=双重峰,t=三重峰,dd=双二重峰,ddd=双二倍二重峰,m=多重峰,q=四重峰,qu=五重峰,sext=六重峰,sept=七重峰,dq=双四重峰,dt=双三重峰。
合成实施例:
编号I-007:2,4-双(二氟甲基)-N-(1,2,4-噻二唑-5-基)吡啶-3-甲酰胺
在室温下,向搅拌着的2,4-双(二氟甲基)吡啶-3-羧酸(150mg,0.672mmol,1.0当量)、1,2,4-噻二唑-5-胺盐酸盐(102mg,0.739mmol,1.1当量)和分子筛于MeCN(10mL)中的混合物中加入1-甲基-1H-咪唑(0.257mL,3.23mmol,4.8当量)。将所得混合物在室温下搅拌20分钟,加入亚硫酰氯(78μL,1.08mmol,1.6当量),然后将反应混合物在70℃下搅拌8h。将反应混合物用水和CH2Cl2的混合物稀释。使用相分离小柱分离有机相,然后减压浓缩。所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(90:10→0:100)洗脱来纯化,得到化合物I-007(24mg,11%产率)。
编号I-009:N-(3-氯-1,2,4-噻二唑-5-基)-2-氟-4-(三氟甲基)吡啶-3-甲酰胺
在室温下,向搅拌着的2-氟-4-(三氟甲基)吡啶-3-羧酸(68.5mg,0.328mmol,1.0当量)、3-氯-1,2,4-噻二唑-5-胺(48.8mg,0.360mmol,1.1当量)和分子筛于MeCN(2mL)中的混合物中加入1-甲基-1H-咪唑(0.125mL,1.57mmol,4.8当量)。将所得混合物在室温下搅拌10分钟,加入亚硫酰氯(38μL,0.524mmol,1.6当量),然后将反应混合物在室温下搅拌24h。将反应混合物用水(5mL)稀释并用CH2Cl2(5mL)萃取。将有机萃取物减压浓缩,所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→0:100)洗脱来纯化,得到化合物I-009(44mg,41%产率),为白色固体。
编号I-016:2-氟-N-(3-甲氧基-1,2,4-噻二唑-5-基)-4-(三氟甲基)吡啶-3-甲酰胺
在室温下,向搅拌着的2-氟-4-(三氟甲基)吡啶-3-羧酸(200mg,0.956mmol,1.0当量)、3-甲氧基-1,2,4-噻二唑-5-胺(138mg,1.05mmol,1.1当量)和分子筛于MeCN(4mL)中的混合物中加入1-甲基-1H-咪唑(366μL,4.59mmol,4.8当量)。将所得混合物在室温下搅拌20分钟,加入亚硫酰氯(112μL,1.53mmol,1.6当量),然后将反应混合物在室温下搅拌48h。将反应混合物用水的混合物稀释,并用CH2Cl2萃取。将有机萃取物用无水Na2SO4干燥,过滤并减压浓缩。所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→0:100)洗脱来纯化,然后通过反相色谱法用水/MeCN洗脱而进行额外纯化得到化合物I-016(65mg,21%产率)。
编号I-020:2,6-二氯-4-甲基-N-(1,2,4-噻二唑-5-基)吡啶-3-甲酰胺
在室温下,向搅拌着的2,6-二氯-4-甲基-吡啶-3-羧酸(150mg,0.728mmol,1.0当量)、1,2,4-噻二唑-5-胺盐酸盐(110mg,0.801mmol,1.1当量)和分子筛于MeCN(3mL)中的混合物中加入1-甲基-1H-咪唑(279μL,3.50mmol,4.8当量)。将所得混合物在室温下搅拌20分钟,加入亚硫酰氯(85μL,1.17mmol,1.6当量),然后将反应混合物在80℃下搅拌4天。将反应混合物用水和CH2Cl2的混合物稀释。使用相分离小柱分离有机相,然后减压浓缩。所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→0:100)洗脱来纯化,得到化合物I-020(48mg,23%产率)。
编I-022:2-溴-4-甲基-N-(1,2,4-噻二唑-5-基)吡啶-3-甲酰胺
在室温下,向搅拌着的2-溴-4-甲基-吡啶-3-羧酸(150mg,0.694mmol,1.0当量)、1,2,4-噻二唑-5-胺盐酸盐(105mg,0.764mmol,1.1当量)和分子筛于MeCN(3mL)中的混合物中加入1-甲基-1H-咪唑(266μL,3.33mmol,4.8当量)。将所得混合物在室温下搅拌20分钟,加入亚硫酰氯(81μL,1.11mmol,1.6当量),然后将反应混合物在80℃下搅拌8h。将反应混合物用水和CH2Cl2的混合物稀释。使用相分离小柱分离有机相,然后减压浓缩。所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→50:50)洗脱来纯化,得到化合物I-022(45mg,21%产率)。
编号VIIa:2-氯-4-异丙基-吡啶-3-羧酸甲酯
在室温下,在氩气气氛下,向搅拌着的2-氯烟酸甲酯(344mg,2.00mmol,1.0当量)于THF中的溶液中逐滴加入BF3.OEt2(0.27mL,2.20mmol,1.1当量)。将所得溶液在0℃下搅拌15分钟,然后进一步冷却至-46℃。逐滴加入i-PrMgCl·LiCl溶液(1.85mL,2.40mmol,1.2当量,1.3M于THF中),在-46℃下进一步搅拌30min。在-46℃下继续加入氯醌(986mg,4.00mmol,2.0当量),将所得混合物加热至室温并搅拌2h。反应混合物用饱和NH3溶液(5ml)淬火,通过硅藻土垫过滤用Et2O(5ml)洗涤。分离相,将水溶液用Et2O(3×5mL)萃取。合并的有机萃取物用无水Na2SO4干燥,过滤并减压浓缩。所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→70:30)洗脱来纯化,得到化合物VIIa(228mg,53%产率),为淡粉色油状物。1H NMR(400MHz,CDCl3):δH 8.36(d,J=4.0Hz,1H),7.20(d,J=4.0Hz,1H),3.97(s,3H),2.92-2.88(m,1H),1.26(d,J=8.0Hz,6H)。
编号VIIIa:2-氯-4-异丙基-吡啶-3-羧酸
在室温下,向搅拌着的化合物VIIa(228mg,1.06mmol,1.0当量)于MeOH(5mL)中的溶液中加入NaOH(3.56mL,21.3mmol,2.0当量,6M水溶液)。得到的混合物在50℃下搅拌2小时。将反应混合物冷却至室温并在减压下去除MeOH。将所得水相酸化,并用EtOAc(5×10mL)萃取。合并的有机萃取物用无水Na2SO4干燥,过滤并减压浓缩,得到化合物VIIIa(208mg,97%),为淡粉色固体。1H NMR(400MHz,CDCl3):δH 8.46(d,J=4.0Hz,1H),7.29(d,J=4.0Hz,1H),3.13-3.10(m,1H),1.32(d,J=8.0Hz,6H)。
编号I-026:2-氯-4-异丙基-N-(1,2,4-噻二唑-5-基)吡啶-3-甲酰胺
在室温下,向搅拌着的化合物VIIIa(120mg,0.60mmol,1.0当量)和1,2,4-噻二唑-5-胺盐酸盐(91mg,0.66mmol,1.1当量)于MeCN(2mL)中的悬浮液中加入1-甲基-1H-咪唑(0.23mL,2.88mmol,4.8当量)。将所得混合物搅拌10分钟,加入亚硫酰氯(70μL,0.96mmol,1.6当量),然后将反应混合物加热至80℃持续36h。将反应混合物用水(5mL)稀释,用CH2Cl2(5mL)萃取,将有机萃取物减压浓缩,所得残余物通过快速柱色谱法在硅胶上用正庚烷/EtOAc(100:0→50:50)洗脱来纯化,得到化合物I-026(59mg,34%产率),为白色固体。
类似于上文举例的和在适当的位置叙述的制备实施例,并考虑到与取代的1,2,4-噻二唑基烟酰胺的制备有关的一般细节,获得下文举例的化合物。
表1:通式(I)的优选化合物的实例
所选表格实施例的波谱数据:
下文列出的所选表格实施例的波谱数据通过常规的1H-NMR说明或NMR峰列表法进行评估。
a)常规的1H-NMR说明
编号I-023:1H-NMR(400MHz,CDCl3):δH 12.85(br.s,1H),8.67-8.54(m,1H),7.98-7.94(m,1H),7.03-6.99(m,1H),2.68(s,3H)。
编号I-026:1H-NMR(400MHz,d6-DMSO):δH 13.82(br.s,1H),8.59(s,1H),8.53-8.49(m,1H),7.62-7.59(s,1H),2.82-2.72(m,1H),1.21(d,J=8.0Hz,6H)。
b)NMR峰列表法
所选实施例的1H-NMR数据以1H-NMR峰列表的形式书写。对于每个信号峰列出以ppm表示的δ值并在圆括号中列出信号强度。δ值-信号强度对之间用分号作为分隔符。
因此,实施例的峰列表具有以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖锐信号的强度与NMR谱的打印实例中的信号高度(以厘米计)相关,并显示信号强度的真实关系。在宽信号的情况下,可以显示几个峰或信号的中间部分以及它们与谱中的最强信号相比的相对强度。
为了校准1H NMR谱的化学位移,我们使用四甲基硅烷和/或所用溶剂的化学位移,尤其是在DMSO中测量波谱的情况下。因此,在NMR峰列表中,可出现但不一定出现四甲基硅烷峰。
1H-NMR峰的列表与常规的1H-NMR打印图类似,并因此通常含有常规的NMR说明中所列出的所有峰。
另外,类似于常规的1H-NMR打印图,它们可显示溶剂信号、目标化合物的立体异构体的信号(其也是本发明的主题)和/或杂质的峰。
为了在溶剂和/或水的δ-范围内显示化合物信号,在我们的1H-NMR峰的列表中显示了常见的溶剂峰,例如在DMSO-D6中DMSO的峰和水的峰,其平均来看通常具有高强度。
目标化合物的立体异构体的峰和/或杂质峰通常平均具有比目标化合物(例如纯度>90%)的峰更低的强度。
此类立体异构体和/或杂质对于特定制备方法来说可能是特有的。因此,它们的峰可通过“副产物指纹”而有助于识别我们的制备方法的重现性。
使用已知方法(MestreC、ACD模拟,还可使用经验评估的预期值)计算目标化合物的峰的专业人员可以视需要任选地使用另外的强度过滤器来分离目标化合物的峰。该分离将与在常规的1H-NMR说明中选出的相关峰类似。
具有峰列表的NMR数据说明的其他详细内容可见于出版物研究公开数据库(Research Disclosure Database Number)第564025号的“Citation of NMR PeaklistData within Patent Applications”。
本发明还提供一种或多种如上文定义的通式(I)的化合物、其盐或N-氧化物的用途,优选在有用植物的作物和/或观赏性植物中作为除草剂和/或植物生长调节剂的用途,所述通式(I)的化合物、其盐或N-氧化物优选为实施方案之一中认定为优选的或特别优选的那些,特别是一种或多种式(I-001)至(I-027)的化合物、其盐或N-氧化物,各自如上文所定义。
本发明还提供一种用于防治有害植物和/或用于调节植物生长的方法,其特征在于,将有效量的以下物质:
-一种或多种如上文定义的通式(I)的化合物、其盐或N-氧化物,优选在实施方案之一中认定为优选的或特别优选的那些,特别是一种或多种式(I-001)至(I-027)的化合物、其盐或N-氧化物,各自如上文所定义,或
-根据本发明的组合物,如下文所定义,
施用至(有害)植物、(有害)植物的种子、(有害)植物生长于其中或其上的土壤或栽培区域。
本发明还提供一种防治不想要的植物、优选在有用植物作物中防治不想要的植物的方法,其特征在于,将有效量的以下物质:
-一种或多种如上文定义的通式(I)的化合物、其盐或N-氧化物,优选在实施方案之一中认定为优选的或特别优选的那些,特别是一种或多种式(I-001)至(I-027)的化合物、其盐或N-氧化物,各自如上文所定义,或
-根据本发明的组合物,如下文所定义,
施用至不想要的植物(例如有害植物,如单子叶或双子叶杂草或不想要的作物植物)、不想要的植物的种子(即植物种子,例如谷粒、种子或无性繁殖器官如块茎或带芽的嫩枝部位)、不想要的植物生长于其中或其上的土壤(例如耕地或非耕地的土壤)或栽培区域(即不想要的植物将生长的区域)。
本发明还提供了调节植物生长、优选调节有用植物生长的方法,其特征在于,将有效量的以下物质:
-一种或多种如上文定义的通式(I)的化合物、其盐或N-氧化物,优选在实施方案之一中认定为优选的或特别优选的那些,特别是一种或多种式(I-001)至(I-027)的化合物、其盐或N-氧化物,各自如上文所定义,或
-根据本发明的组合物,如下文所定义,
施用至植物、植物的种子(即植物种子,例如谷粒、种子或无性繁殖器官如块茎或带芽的嫩枝部位)、植物生长于其中或其上的土壤(例如耕地或非耕地的土壤)或栽培区域(即植物将生长的区域)。
在本发明的上下文中,本发明的化合物或本发明的组合物可例如通过播种前(如果合适,还通过引掺入土壤中)、苗前和/或苗后的方法施用。可通过本发明的化合物防治的一些代表性的单子叶及双子叶杂草植物群的具体实例如下,但不旨在将列举限于特定种类。
在用于防治有害植物或调节植物生长的本发明的方法中,一种或多种的通式(I)的化合物、其盐或N-氧化物优选用于在有用植物作物或观赏植物中防治有害植物或调节生长,其中在一个优选的实施方案中,有用植物或观赏植物为转基因植物。
本发明的通式(I)的化合物和/或其盐和N-氧化物适合于防治以下属的单子叶和双子叶有害植物:
以下属的单子叶有害植物:山羊草属(Aegilops)、冰草属(Agropyron)、剪股颖属(Agrostis)、看麦娘属(Alopecurus)、Apera、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、鸭跖草属(Commelina)、狗牙根属(Cynodon)、莎草属(Cyperus)、龙爪茅属(Dactyloctenium)、马唐属(Digitaria)、稗属(Echinochloa)、荸荠属(Eleocharis)、穇属(Eleusine)、画眉草属(Eragrostis)、野黍属(Eriochloa)、羊茅属(Festuca)、飘拂草属(Fimbristylis)、异蕊花属(Heteranthera)、白茅属(Imperata)、鸭嘴草属(Ischaemum)、千金子属(Leptochloa)、黑麦草属(Lolium)、雨久花属(Monochoria)、黍属(Panicum)、雀稗属(Paspalum)、虉草属(Phalaris)、梯牧草属(Phleum)、早熟禾属(Poa)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、莞草属(Scirpus)、狗尾草属(Setaria)和高粱属(Sorghum)。
以下属的双子叶有害植物:茼麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、Anoda、春黄菊属(Anthemis)、Aphanes、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针属(Bidens)、荠属(Capsella)、飞廉属(Carduus)、决明属(Cassia)、矢车菊属(Centaurea)、藜属(Chenopodium)、蓟属(Cirsium)、旋花属(Convolvulus)、曼陀罗属(Datura)、山蚂蝗属(Desmodium)、刺酸模属(Emex)、糖芥属(Erysimum)、大戟属(Euphorbia)、鼬瓣花属(Galeopsis)、牛膝菊属(Galinsoga)、拉拉藤属(Galium)、木槿属(Hibiscus)、番薯属(Ipomoea)、地肤属(Kochia)、野芝麻属(Lamium)、独行菜属(Lepidium)、母草属(Lindernia)、母菊属(Matricaria)、薄荷属(Mentha)、山靛属(Mercurialis)、Mullugo、勿忘草属(Myosotis)、罂粟属(Papaver)、牵牛属(Pharbitis)、车前属(Plantago)、蓼属(Polygonum)、马齿苋属(Portulaca)、毛茛属(Ranunculus)、萝卜属(Raphanus)、蔊菜属(Rorippa)、节节菜属(Rotala)、酸模属(Rumex)、猪毛菜属(Salsola)、千里光属(Senecio)、田菁属(Sesbania)、黄花稔属(Sida)、欧白芥属(Sinapis)、茄属(Solanum)、苦苣菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、车轴草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)和苍耳属(Xanthium)。
当将本发明的化合物在有害植物(禾本科杂草和/或阔叶杂草)萌芽前施用于土壤表面时(苗前法),完全阻止禾本科杂草或阔叶杂草的幼苗出苗,或者它们生长直至它们达到子叶期,但随后停止生长,并最终在三至四周后彻底死亡。
如果将活性化合物在苗后施用于植物的绿色部位,则在处理后停止生长,并且有害植物停留在施用时的生长阶段,或者它们在一定时间后彻底死亡,由此以这样的方式非常早地且以持久的方式消除对作物植物有害的杂草的竞争。
尽管本发明的化合物表现出显著的抵抗单子叶及双子叶杂草的除草活性,但根据本发明的各个化合物的结构及其施用率,对经济上重要的作物的作物植物仅造成微不足道的损害或完全没有损害,所述经济上重要的作物为例如以下属的双子叶作物:花生属(Arachis)、甜菜属(Beta)、芸苔属(Brassica)、黄瓜属(Cucumis)、南瓜属(Cucurbita)、向日葵属(Helianthus)、胡萝卜属(Daucus)、大豆属(Glycine)、棉属(Gossypium)、番薯属(Ipomoea)、莴苣属(Lactuca)、亚麻属(Linum)、番茄属(Lycopersicon)、芒属(Miscanthus)、烟草属(Nicotiana)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、蚕豆属(Vicia);或以下属的单子叶作物:葱属(Allium)、凤梨属(Ananas)、天门冬属(Asparagus)、燕麦属(Avena)、大麦属(Hordeum)、稻属(Oryza)、黍属(Panicum)、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属(Sorghum)、小黑麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea)。出于这些理由,本发明的化合物非常适于选择性防治植物作物(例如农业上的有用植物或观赏植物)中不想要的植物生长。
此外,本发明的化合物(根据其具体的结构和所使用的施用率)对作物植物具有显著的生长调节特性。它们干预植物自身的代谢并具有调节效果,并因此可用于受控地影响植物成分并促进采收,例如通过引发脱水和矮化生长。此外,它们还适于普遍的防治和抑制不想要的营养生长而不在该过程中杀死植物。抑制营养生长对许多单子叶及双子叶作物起到重要作用,因为例如其可减少或完全防止倒伏。
由于活性化合物具有除草特性及植物生长调节特性,其也可用于防治遗传修饰植物作物或通过常规诱变而改性的植物作物中的有害植物。通常,转基因植物的特征在于特别有利的特性,例如对某些农药(特别是某些除草剂)具有抗性,对植物病害或植物病害的病原体具有抗性,所述病原体为例如某些昆虫或微生物(例如真菌、细菌或病毒)。其他具体的特征涉及例如采收物的数量、质量、贮存性、组成及具体成分。例如,已知具有增加的淀粉含量或改变的淀粉质量的转基因植物,或在采收材料中具有不同的脂肪酸组成的那些转基因植物。
鉴于转基因作物,优选将本发明的化合物和/或其盐和N-氧化物用于经济上重要的有用植物和观赏植物的转基因作物中,例如谷类如小麦、大麦、黑麦、燕麦、粟、稻和玉米的转基因作物中,或者甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆及其他蔬菜的作物中。
优选将本发明的化合物作为除草剂施用于对除草剂的植物毒性效应具有抗性或通过重组方式使其具有抗性的有用植物作物中。
由于活性化合物具有除草特性及植物生长调节特性,其还可用于防治已知的或尚未开发的遗传修饰植物作物中的有害植物。通常,转基因植物的特征在于特别有利的特性,例如对某些农药(特别是某些除草剂)具有抗性,对植物病害或植物病害的病原体具有抗性,所述病原体为例如某些昆虫或微生物(例如真菌、细菌或病毒)。其他特定的特征涉及例如采收物的数量、质量、贮存性、组成及具体成分。例如,存在已知的具有增加的淀粉含量或改变的淀粉质量的转基因植物,或在采收材料中具有不同的脂肪酸组成的那些转基因植物。其他特殊的特性可为对非生物胁迫(例如热、低温、干旱、盐度和紫外辐射)具有耐受性或抗性。
优选本发明的通式(I)的化合物和/或其盐和N-氧化物在经济上重要的有用植物和观赏植物的转基因作物中的用途,例如在谷类,如小麦、大麦、黑麦、燕麦、黑小麦、粟、稻、木薯和玉米的转基因作物中的用途,或者在甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆及其他蔬菜的作物中的用途。
可优选将通式(I)的化合物作为除草剂用于对除草剂的植物毒性效应具有抗性或通过重组方式使其具有抗性的有用植物的作物中。
产生与现有植物相比具有改性特性的新植物的常规方法包括,例如常规栽培方法和产生突变体。或者,可借助重组方法产生具有改变特性的新植物。
本领域技术人员已知大量的可借助其来产生新的具有改性特性的转基因植物的分子生物技术。对于此类重组操作,可将允许通过DNA序列重组而产生突变或序列改变的核酸分子引入质粒中。借助标准方法,例如,可进行碱基交换、移除部分序列或者添加天然或合成序列。为了使DNA片段彼此连接,可向片段中添加衔接子或接头。
例如,具有降低的基因产物活性的植物细胞的产生可通过以下方式实现:通过表达至少一种相应的反义RNA、用于实现共抑制效应的正义RNA;或者通过表达至少一种适当构建的核酶,所述核酶特异性切割上述基因产物的转录物。
为此,首先可使用含有基因产物的完整编码序列(包括可存在的任何侧翼序列)的DNA分子,以及仅含有部分编码序列的DNA分子,在该情况下,这些部分必须足够长以在细胞中产生反义效果。也可使用与基因产物的编码序列具有高度的同源性但与它们不完全相同的DNA序列。
当表达植物中的核酸分子时,所合成的蛋白质可定位于植物细胞的任何所需的区室中。但是,为实现在特定区室中的定位,可以例如将编码区连接到确保在特定区室中定位的DNA序列。这类序列是本领域技术人员已知的(参见,例如Braun等,EMBO J.11(1992),3219-3227)。核酸分子还可在植物细胞的细胞器中表达。
转基因植物细胞可通过已知技术再生以得到完整植株。原则上,转基因植物可为任何所需的植物物种的植物,即不仅可为单子叶植物,还可为双子叶植物。
因此,可获得这样的转基因植物,其特性通过过表达、阻抑或抑制同源(=天然)基因或基因序列或者表达异源(=外源)基因或基因序列而改变。
优选将本发明的化合物(I)用在对以下物质具有抗性的转基因作物中:生长调节剂,例如麦草畏(dicamba);或抑制植物必需酶的除草剂,所述酶为例如乙酰乳酸合酶(ALS)、EPSP合酶、谷氨酰胺合成酶(GS)或羟苯丙酮酸双加氧酶(HPPD);或选自磺酰脲、草甘膦、草铵膦或苯甲酰基异噁唑和类似活性化合物的除草剂。
当将本发明的活性化合物用于转基因作物时,不仅出现在其他作物中观察到的对有害植物的作用,还经常出现在施用于特定转基因作物时的特异性的作用,例如改变的或特别地拓宽的可防治的杂草谱,改变的可用于施用的施用率,优选地与转基因作物对其具有抗性的除草剂的良好结合性,以及影响转基因作物植物的生长和产率。
因此,本发明还涉及本发明的通式(I)的化合物和/或其盐和N-氧化物作为除草剂用于防治有用植物作物或观赏植物、任选地转基因作物植物中的有害植物的用途。
优选通过苗前法或苗后法在谷类(此处优选玉米、小麦、大麦、黑麦、燕麦、粟或稻)中的用途。
还优选通过苗前法或苗后法在大豆中的用途。
根据本发明,用于防治有害植物或用于植物生长调节的用途还包括如下情况:其中通式(I)的活性化合物或其盐直至在施用于植物上、植物中或土壤中之后才由前体物质(“前药”)形成。
本发明还提供了一种或多种的通式(I)的化合物、其盐或N-氧化物或(如下定义的)本发明的组合物(在一种方法中)用于防治有害植物或用于调节植物生长的用途,其包括向植物(有害植物,如果合适,连同有用植物一起)、植物种子、植物生长于其中或其上的土壤或栽培区域施用有效量的一种或多种的通式(I)的化合物、其盐或N-氧化物。
本发明还提供了除草的和/或植物生长调节的组合物,其特征在于,该组合物包含:
(a)一种或多种如上文定义的通式(I)的化合物、其盐或N-氧化物,优选在实施方案之一中认定为优选的或特别优选的,特别是一种或多种式(I-001)至(I-027)的化合物、其盐或N-氧化物,各自如上文所定义,以及
(b)一种或多种的选自组(i)和/或(ii)的其他物质:
(i)一种或多种的其他农业化学活性物质,优选选自杀昆虫剂、杀螨剂、杀线虫剂、其他除草剂(即不符合上文定义的通式(I)的那些)、杀真菌剂、安全剂、肥料和/或其他生长调节剂,
(ii)一种或多种的作物保护中常规的制剂助剂。
在这里,本发明组合物的组分(i)的其他农业化学活性物质优选选自“农药手册(The Pesticide Manual)”,第16版,The British Crop Protection Council and theRoyal Soc.of Chemistry,2012中提及的物质。
本发明的除草的或植物生长调节的组合物优选包含一种、两种、三种或更多种作物保护中常规的制剂助剂(ii),所述制剂助剂选自表面活性剂、乳化剂、分散剂、成膜剂、增稠剂、无机盐、除尘剂、在25℃和1013毫巴下为固体的载体(优选吸附性颗粒状惰性物质)、润湿剂、抗氧化剂、稳定剂、缓冲物质、消泡剂、水、有机溶剂,优选在25℃和1013毫巴下可与水以任意比例混溶的有机溶剂。
本发明通式的(I)化合物可以常规制剂中的可湿性粉剂、乳油、可喷雾溶液剂、粉剂或颗粒剂的形式使用。因此,本发明还提供了包含通式(I)的化合物,其盐或N-氧化物的除草组合物和植物生长调节组合物。
通式(I)的化合物、其盐或N-氧化物可以多种方式根据所需的生物学和/或物理化学参数进行配制。可行的制剂包括例如:可湿性粉剂(WP),水溶性粉剂(SP),水溶性浓缩剂,乳油(EC),乳剂(EW)(如水包油乳剂和油包水乳剂),可喷雾溶液剂,悬浮剂(SC),油基或水基分散剂,可与油混溶的溶液剂,胶囊悬浮剂(CS),粉剂(DP),拌种产品,用于撒播和土壤施用的颗粒剂,呈微粒、喷雾颗粒、吸收和吸附颗粒形式的颗粒剂(GR),水分散粒剂(WG),水溶性颗粒剂(SG),ULV制剂,微胶囊剂,和蜡剂。
这些单独的制剂类型和制剂助剂(例如惰性物质、表面活性剂、溶剂和其他添加剂)是本领域技术人员已知的,并且记载于例如下列文献中:Watkins,"Handbook ofInsecticide Dust Diluents and Carriers",第二版,Darland Books,Caldwell N.J.;H.v.Olphen,"Introduction to Clay Colloid Chemistry",第二版,J.Wiley&Sons,N.Y.;C.Marsden,"Solvents Guide",第二版,Interscience,N.Y.1963;McCutcheon's"Detergents and Emulsifiers Annual",MC Publ.Corp.,Ridgewood N.J.;Sisley andWood,"Encyclopedia of Surface Active Agents",Chem.Publ.Co.Inc.,N.Y.1964; [Interface-activeEthylene Oxide Adducts],Wiss.Verlagsgesellschaft,Stuttgart 1976;Winnacker-Küchler,"Chemische Technologie"[Chemical Technology],第七卷,C.Hanser VerlagMunich,第4版,1986。
可湿性粉剂为这样的制剂,其可均匀分散在水中,并且,除活性化合物外,除稀释剂或惰性物质外,还含有离子型和/或非离子型表面活性剂(润湿剂、分散剂),例如聚氧乙基化烷基酚、聚氧乙基化脂肪醇、聚氧乙基化脂肪胺、脂肪醇聚乙二醇醚硫酸盐、烷烃磺酸盐、烷基苯磺酸盐、木素磺酸钠、2,2’-二萘基甲烷-6,6’-二磺酸钠、二丁基萘磺酸钠或油酰基甲基牛磺酸钠。为制备可湿性粉剂,将除草活性化合物精细研磨,例如在常规装置例如锤式研磨机、鼓风式研磨机和空气喷射式研磨机中精细研磨,并同时或随后与制剂助剂混合。
乳油通过下列方法制备:将活性化合物溶解在有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或较高沸点的芳族化合物或烃类)或有机溶剂的混合物中,并加入一种或多种的离子和/或非离子型表面活性剂(乳化剂)。可用的乳化剂的实例为:烷基芳基磺酸钙,例如十二烷基苯磺酸钙;或非离子型乳化剂,例如脂肪酸聚乙二醇酯、烷基芳基聚乙二醇醚、脂肪醇聚乙二醇醚、环氧丙烷-环氧乙烷缩合产物、烷基聚醚、脱水山梨糖醇酯(例如脱水山梨糖醇脂肪酸酯)或聚氧乙烯脱水山梨糖醇酯(例如聚氧乙烯脱水山梨糖醇脂肪酸酯)。
粉剂通过将活性化合物与细分布的固体一起研磨而获得,所述固体为例如滑石、天然粘土(例如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮剂可为水基或油基的。它们可例如借助市售的珠磨机并任选地添加例如已在上文针对其他制剂类型所列的表面活性剂通过湿磨而制备。
乳剂,例如水包油型乳剂(EW),可例如借助搅拌机、胶体磨机和/或静态混合器使用含水有机溶剂和任选地例如已在上文针对其他制剂类型所列的表面活性剂而制备。
颗粒剂可通过将活性化合物喷洒至吸附性颗粒状惰性材料上而制备,或者借助粘合剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)将活性化合物浓缩剂施用到载体(例如砂、高岭土或颗粒状惰性材料)的表面而制备。还可以将适宜的活性化合物以常用于制备肥料颗粒的方式(如果需要,以与肥料的混合物的形式)进行造粒。
水分散粒剂通常通过常规方法例如喷雾干燥法、流化床制粒法、盘式制粒法用高速混合器混合并在不使用固体惰性材料的情况下挤出而制备。
关于盘式颗粒、流化床颗粒、挤出机颗粒及喷雾颗粒的制备,参见例如下列文献中的方法:"Spray Drying Handbook"第三版,1979,G.Goodwin Ltd.,London,J.E.Browning,"Agglomeration",Chemical and Engineering 1967,第147页起;"Perry'sChemical Engineer's Handbook",第五版,McGraw Hill,New York 1973,第8-57页。
关于作物保护组合物制剂的其他详细内容,参见例如G.C.Klingman,"WeedControl as a Science",John Wiley and Sons,Inc.,New York,1961,第81-96页和J.D.Freyer,S.A.Evans,"Weed Control Handbook",第五版,Blackwell ScientificPublications,Oxford,1968,第101-103页。
本发明的农业化学制剂(优选除草的或植物生长调节的组合物)优选含有总量为0.1-99重量%、优选0.5-95重量%、特别优选1-90重量%、尤其优选2-80重量%的通式(I)的活性化合物、其盐或N-氧化物。
在可湿性粉剂中,活性化合物浓度为例如约10-90重量%,至100重量%的余量物质由常规制剂组分组成。在乳油中,活性化合物浓度可为约1至90重量%以及优选5至80重量%。粉末形式的制剂包含1至30重量%的活性化合物,通常优选5至20重量%的活性化合物;可喷雾溶液剂包含约0.05至80重量%、优选2至50重量%的活性化合物。在水分散粒剂的情况下,活性化合物的含量部分地取决于活性化合物呈液体形式还是固体形式,以及取决于所使用的造粒助剂、填料等。在水分散粒剂中,活性化合物的含量在例如1至95重量%之间、优选在10至80重量%之间。
此外,所提及的活性化合物制剂任选地包含相应的常规的粘着剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、抗冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂以及影响pH和粘度的剂。制剂助剂的实例尤其记载于“Chemistry and Technology ofAgrochemical Formulations”,编辑D.A.Knowles,Kluwer Academic Publishers(1998)中。
通式(I)的化合物、其盐或N-氧化物可按原样使用或以其与其他农药活性化合物(例如杀昆虫剂、杀螨剂、杀线虫剂、除草剂、杀真菌剂、安全剂、肥料和/或生长调节剂)结合的制剂(preparation)(制剂(formulation))的形式使用,例如以成品制剂的形式或桶混物的形式使用。可基于上述制剂同时考虑待结合的活性化合物的物理特性和稳定性制备结合制剂。
可与本发明的通式(I)的化合物以混合制剂或以桶混物形式结合使用的活性化合物为例如基于对以下酶的抑制作用的已知活性化合物:例如乙酰乳酸合酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇丙酮酰莽草酸-3-磷酸合酶(enolpyruvylshikimate-3-phosphatesynthase)、谷氨酰胺合成酶、对羟苯丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II、原卟啉原氧化酶,例如,如Weed Research 26(1986)441-445或"The PesticideManual",第十六版,The British Crop Protection Council and the Royal Soc.ofChemistry,2012及其中引用的文献中所记载的。
特别关注的是选择性防治有用植物作物和观赏植物中的有害植物。尽管已经非常好地证明了本发明通式(I)的化合物在大量的作物中——原则上,在一些作物中——以及尤其是在与其他选择性较低的除草剂的混合物的情况下,可能出现对作物植物的植物毒性。对此,特别关注的是本发明通式(I)的化合物的结合物,其含有通式(I)的化合物或其与其他除草剂或农药和安全剂的结合物。以解毒有效量使用的安全剂降低了例如在经济上重要的作物中使用的除草剂/农药的植物毒性副作用,所述经济上重要的作物为例如谷类(小麦、大麦、黑麦、玉米、稻、粟)、甜菜、甘蔗、油菜、棉花和大豆,优选谷类。
除草剂(混合物)与安全剂的重量比通常取决于除草剂施用率和所述安全剂的功效,并且可在宽范围内变化,例如在200:1至1:200、优选100:1至1:100、特别是20:1至1:20的范围内变化。与化合物(I)或其混合物类似,安全剂可与其他除草剂/农药一起配制,并且可作为成品制剂或与除草剂的桶混物提供和施用。
为了施用,如果合适,将以市售形式存在的除草剂或除草剂/安全剂制剂以常规方式稀释,例如在可湿性粉剂、乳油、分散剂和水分散粒剂的情况下使用水稀释。粉型制剂、用于土壤施用的颗粒剂或用于撒播的颗粒剂以及可喷雾溶液剂在施用前通常无需用其他惰性物质进一步稀释。
通式(I)的化合物、其盐或N-氧化物的施用率在一定程度上受外部条件(例如温度、湿度等)影响。在本文中,施用率可在宽范围内变化。对于作为除草剂用于防治有害植物的施用,通式(I)的化合物、其盐或N-氧化物的总量优选在0.001至10.0kg/ha范围内、优选在0.005至5kg/ha范围内、更优选在0.01至1.5kg/ha范围内、特别是在0.05至1kg/ha范围内。这同时适用于苗前法和苗后法施用。
当通式(I)的化合物、其盐或N-氧化物用作植物生长调节剂时,例如用作作物植物的茎秆稳定剂时,所述作物植物如上文提及的那些,优选谷类植物,例如小麦、大麦、黑麦、黑小麦、粟、稻或玉米,总施用率优选在0.001至2kg/ha的范围内、优选在0.005至1kg/ha的范围内、特别是10至500g/ha的范围内、非常特别是20至250g/ha的范围内。这同时适用于苗前和苗后施用。
作为茎秆稳定剂的施用可在植物生长的各个阶段进行。优选例如在耕作期后、纵向生长开始时施用。
作为替代方案,作为植物生长调节剂的施用也可通过处理种子进行,其包括拌种和种子包衣的多种技术。在本文中,施用率取决于具体的技术并且可在预试验中确定。
可在本发明的组合物中与本发明通式(I)的化合物(例如以混合制剂形式或以桶混物形式)结合使用的活性化合物为,例如已知的基于抑制以下物质的活性化合物:例如乙酰乳酸合酶、乙酰辅酶A羧化酶、纤维素合酶、烯醇丙酮酰莽草酸-3-磷酸合酶、谷氨酰胺合酶、对羟基苯丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II、原卟啉原氧化酶(protoporphyrinogen oxidase),如例如Weed Research 26(1986)441-445或"ThePesticide Manual",第16版,The British Crop Protection Council and the RoyalSoc.of Chemistry,2012以及其中引用的文献中所记载。可与本发明的化合物结合的已知的除草剂或植物生长调节剂为例如以下活性化合物,其中所述活性化合物以根据国际标准化组织(ISO)的“通用名称”命名,或以化学名称或代码编号命名。即使未明确提及,它们也总是包括所有的施用形式,例如酸、盐、酯以及所有的异构体形式,例如立体异构体和光学异构体。
这类除草混合配伍剂(partner)的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen)、三氟羧草醚甲酯(acifluorfen-methyl)、三氟羧草醚钠盐(acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、禾草灭钠盐(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、先甲草胺(amidochlor)、酰嘧磺隆(amidosulfuron)、4-氨基-3-氯-6-(4-氯-2-氟-3-甲基苯基)-5-氟吡啶-2-甲酸、环丙嘧啶酸(aminocyclopyrachlor)、环丙嘧啶酸钾盐(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、氯氨吡啶酸-二甲基铵(aminopyralid-dimethylammonium)、aminopyralid-tripromine、杀草强(amitrole)、氨基磺酸铵、莎稗磷(anilofos)、磺草灵(asulam)、磺草灵钾盐(asulam-potassium)、磺草灵钠盐(asulam-sodium)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、(S)-(-)-氟丁酰草胺((S)-(-)-beflubutamid)、beflubutamid-M、草除灵(benazolin)、草除灵乙酯(benazolin-ethyl)、草除灵-二甲基铵(benazolin-dimethylammonium)、草除灵钾盐(benazolin-potassium)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron)、苄嘧磺隆甲酯(bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、灭草松钠盐(bentazone-sodium)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyrone)、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、bipyrazone、双草醚(bispyribac)、双草醚钠盐(bispyribac-sodium)、二氯异噁草酮(bixlozone)、除草定(bromacil)、除草定锂盐(bromacil-lithium)、除草定钠盐(bromacil-sodium)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴苯腈丁酸盐(bromoxynil-butyrate)、溴苯腈钾盐(bromoxynil-potassium)、溴苯腈庚酸盐(bromoxynil-heptanoate)和溴苯腈辛酸盐(bromoxynil-octanoate)、羟草酮(busoxinone)、丁草胺(butachlor)、氟丙嘧草酯(butafenacil)、抑草磷(butamifos)、丁烯草胺(butenachlor)、仲丁灵(butralin)、丁氧环酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、克草胺酯(cambendichlor)、双酰草胺(carbetamide)、氟唑草酮(carfentrazone),氟唑草酮乙酯(carfentrazone-ethyl)、草灭畏(chloramben)、草灭畏铵盐(chloramben-ammonium)、草灭畏二乙醇胺(chloramben-diolamine)、草灭畏甲酯(chloramben-methyl)、草灭畏甲基铵盐(chloramben-methylammonium)、草灭畏钠盐(chloramben-sodium)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、伐草克铵盐(chlorfenac-ammonium)、伐草克钠盐(chlorfenac-sodium)、燕麦酯(chlorfenprop)、燕麦甲酯(chlorfenprop-methyl)、氯芴素(chlorflurenol)、氯芴素甲酯(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron)、氯嘧磺隆乙酯(chlorimuron-ethyl)、氯酞酰亚胺(chlorophthalim)、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、敌草索(chlorthal)、氯酞酸甲酯(chlorthal-dimethyl)、氯酞酸单甲酯(chlorthal-monomethyl)、吲哚酮草酯(cinidon)、吲哚酮草酯(cinidon-ethyl)、环庚草醚(cinmethylin)、exo-(+)-环庚草醚(即,(1R,2S,4S)-4-异丙基-1-甲基-2-[(2-甲基苄基)氧基]-7-氧杂双环[2.2.1]庚烷)、exo-(-)-环庚草醚(即,(1R,2S,4S)-4-异丙基-1-甲基-2-[(2-甲基苄基)氧基]-7-氧杂双环[2.2.1]庚烷)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酸乙酯(clodinafop-ethyl)、炔草酯(clodinafop-propargyl)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、二氯吡啶酸甲酯(clopyralid-methyl)、二氯吡啶酸乙醇胺(clopyralid-olamine)、二氯吡啶酸钾盐(clopyralid-potassium)、clopyralid-tripomine、氯酯磺草胺酸(cloransulam)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氨氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyranil、cyclopyrimorate、环胺磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、cyhalofop、氰氟草酯(cyhalofop-butyl)、环丙津(cyprazine)、2,4-D(包括2,4-D铵、2,4-D-丁氧基乙基酯(2,4-D-butoyl)、2,4-D-丁基酯、2,4-D-胆碱、2,4-D-二乙基铵、2,4-D-二甲基铵、2,4-D-二醇胺、2,4-D-doboxyl、2,4-D-十二烷基铵、2,4-D-etexyl、2,4-D-乙基酯、2,4-D-2-乙基己基酯、2,4-D-庚基铵、2,4-D-异丁基酯、2,4-D-异辛基酯、2,4-D-异丙基、2,4-D-异丙基铵、2,4-D-锂、2,4-D-meptyl、2,4-D-甲基酯、2,4-D-钾、2,4-D-十四烷基铵、2,4-D-三乙基铵、2,4-D-三异丙醇铵、2,4-D-tripromine及2,4-D-三乙醇胺(2,4-D-trolamine),其盐)、2,4-DB、2,4-DB-丁基酯、2,4-DB-二甲基铵、2,4-DB-异辛基酯、2,4-DB-钾和2,4-DB-钠、杀草隆(daimuron(dymron))、茅草枯(dalapon)、茅草枯-钙盐(dalapon-calcium)、茅草枯镁盐(dalapon-magnesium)、茅草枯钠盐(dalapon-sodium)、棉隆(dazomet)、棉隆钠盐(dazomet-sodium)、正癸醇、7-脱氧-D-景天庚酮糖(7-deoxy-D-sedoheptulose)、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏(dicamba)及其盐(例如dicamba-biproamine、麦草畏-N,N-双(3-氨基丙基)甲胺、麦草畏丁氧基乙基酯(dicamba-butotyl)、麦草畏胆碱(dicamba-choline)、麦草畏二甘醇胺盐(dicamba-diglycolamine)、麦草畏二甲基铵(dicamba-dimethylammonium)、麦草畏二乙醇铵(dicamba-diethanolaminemmonium)、麦草畏二乙基铵(dicamba-diethylammonium)、麦草畏异丙基铵(dicamba-isopropylammonium)、麦草畏甲酯(dicamba-methyl)、麦草畏单乙醇胺(dicamba-monoethanolamine)、麦草畏醇胺(dicamba-olamine)、麦草畏钾盐(dicamba-potassium)、麦草畏钠盐(dicamba-sodium)、麦草畏三乙醇胺(dicamba-triethanolamine))、敌草腈(dichlobenil)、2-(2,4-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2-(2,5-二氯苄基)-4,4-二甲基-1,2-噁唑烷-3-酮、2,4-滴丙酸(dichlorprop)、2,4-滴丙酸丁氧基酯(dichlorprop-butotyl)、2,4-滴丙酸二甲基铵(dichlorprop-dimethylammonium)、dichlorprop-etexyl、2,4-滴丙酸乙铵(dichlorprop-ethylammonium)、2,4-滴丙酸异辛酯(dichlorprop-isoctyl)、2,4-滴丙酸甲酯(dichlorprop-methyl)、2,4-滴丙酸钾盐(dichlorprop-potassium)、2,4-滴丙酸钠盐(dichlorprop-sodium)、精2,4-滴丙酸(dichlorprop-P)、精2,4-滴丙酸二甲基铵(dichlorprop-P-dimethylammonium)、dichlorprop-P-etexyl、精2,4-滴丙酸钾盐(dichlorprop-P-potassium)精2,4-滴丙酸钠盐(dichlorprop-sodium)、二氯苯氧基丙酸(diclofop)、禾草灵(diclofop-methyl)、精禾草灵(diclofop-P)、精禾草灵(diclofop-P-methyl)、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、野燕枯(difenzoquat-metilsulfate)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、二氟吡隆钠(diflufenzopyr-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、dimesulfazet、二甲草胺(dimethachlor)、异戊乙净(dimethametryn)、二甲吩草胺(dimethenamid)、精二甲吩草胺(dimethenamid-P)、dimetrasulfuron、氨氟灵(dinitramine)、特乐酚(dinoterb)、特乐酯(dinoterb-acetate)、双苯酰草胺(diphenamid)、敌草快(diquat)、二溴敌草快(diquat-dibromid)、二氯敌草快(diquat-dichloride)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、DNOC-铵(DNOC-ammonium)、DNOC-钾(DNOC-potassium)、DNOC-钠(DNOC-sodium)、茵多酸(endothal)、茵多酸-二铵(endothal-diammonium)、茵多酸-二钾(endothal-dipotassium)、茵多酸-二钠(endothal-disodium)、epyrifenacil(S-3100)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、甲基胺苯磺隆(ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氟乳醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-5231(即N-[2-氯-4-氟-5-[4-(3-氟丙基)-4,5-二氢-5-氧代-1H-四唑-1-基]苯基]乙磺酰胺)、F-7967(即,3-[7-氯-5-氟-2-(三氟甲基)-1H-苯并咪唑-4-基]-1-甲基-6-(三氟甲基)嘧啶-2,4(1H,3H)-二酮)、唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵乙酯(fenoxaprop-ethyl)、精噁唑禾草灵乙酯(fenoxaprop-P-ethyl)、芬诺杀磺隆(fenoxasulfone)、苯唑氟草酮(fenpyrazone)、fenquinotrione、四唑酰草胺(fentrazamide)、麦草氟(flamprop)、麦草氟异丙基酯(flamprop-isoproyl)、麦草氟甲酯(flamprop-methyl)、高效麦草氟异丙酯(flamprop-M-isopropyl)、高效麦草氟甲酯(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、florpyrauxifen、florpyrauxifen-benzyl、吡氟禾草灵(fluazifop)、吡氟禾草灵丁酯(fluazifop-butyl)、吡氟禾草灵甲酯(fluazifop-methyl)、精吡氟禾草灵(fluazifop-P)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟酮磺隆(flucarbazone)、氟酮磺隆钠盐(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、flufenpyr、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸戊酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、9-羟基芴甲酸(flurenol)、芴丁酯(flurenol-butyl)、芴二甲基铵(flurenol-dimethylammonium)和芴甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen),乙羧氟草醚乙酯(fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、四氟丙酸钠盐(flupropanate-sodium)、氟啶嘧磺隆(flupyrsulfuron)、氟啶嘧磺隆甲酯(flupyrsulfuron-methyl)、氟啶嘧磺隆甲酯钠盐(flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr)、fluroxypyr-butometyl、氯氟吡氧乙酸-甲基庚酯(fluroxypyr-meptyl)、呋草酮(flurtamone)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺胺草醚钠盐(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、甲酰氨磺隆钠盐(foramsulfuron-sodium salt)、杀木膦(fosamine)、杀木膦铵盐(fosamine-ammonium)、草铵膦(glufosinate)、草铵膦铵盐(glufosinate-ammonium)、草铵膦钠盐(glufosinate-sodium)、L-草铵膦铵盐(L-glufosinate-ammonium)、L-草铵膦钠盐(L-glufosinate-sodium)、精草铵膦钠盐(glufosinate-P-sodium)、精草铵膦铵盐(glufosinate-P-ammonium)、草甘膦(glyphosate)、草甘膦铵(glyphosate-ammonium)、草甘膦异丙基铵(glyphosate-isopropylammonium)、草甘膦二胺(glyphosate-diammonium)、草甘膦二甲基铵(glyphosate-dimethylammonium)、草甘膦钾(glyphosate-potassium)、草甘膦钠盐(glyphosate-sodium)、草甘膦倍半钠盐(glyphosate-sesquisodium)和草甘膦三甲基锍盐(glyphosate-trimesium)、H-9201(即O-(2,4-二甲基-6-硝基苯基)-O-乙基异丙基硫代磷酰胺酯(O-(2,4-dimethyl-6-nitrophenyl)-O-ethylisopropylphosphoramidothioate))、氟氯吡啶酸(halauxifen)、氟氯吡啶酯(halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、氯吡嘧磺隆甲酯(halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯(haloxyfop-ethoxyethyl)、精氟吡禾灵乙氧基乙酯(haloxyfop-P-ethoxyethyl)、氟吡禾灵甲酯(haloxyfop-methyl)、精氟吡禾灵甲酯(haloxyfop-P-methyl)、氟吡禾灵钠盐(haloxifop-sodium)、环嗪酮(hexazinone)、HNPC-A8169(即,(2S)-2-{3-[(5-叔丁基吡啶-2-基)氧基]苯氧基}丙酸丙-2-炔-1-基酯)、HW-02(即,(2,4-二氯苯氧基)乙酸1-(二甲氧基磷酰基)乙基酯)、hydantocidin、咪草酸(imazamethabenz)、咪草酸甲酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵盐(imazamox-ammonium)、甲咪唑烟酸(imazapic),甲咪唑烟酸铵盐(imazapic-ammonium)、咪唑烟酸(imazapyr)、咪唑烟酸异丙铵(imazapyr-isopropylammonium)、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵(imazaquin-ammonium)、咪唑喹啉酸甲酯(imazaquin-methyl)、咪草烟(imazethapyr)、咪草烟亚铵盐(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、碘甲磺隆(iodosulfuron)、碘甲磺隆(iodosulfuron-methyl)、碘甲磺隆钠盐(iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、碘苯腈锂盐(ioxynil-lithium)、碘苯腈辛酸酯(ioxynil-octanoate)、碘苯腈钾(ioxynil-potassium)和碘苯腈钠(ioxynil-sodium)、卤苯胺唑(ipfencarbazone)、异丙隆(isoproturon)、异隆(isouron)、异噁酰草胺(isoxaben)、异噁唑草酮(isoxaflutole)、特胺灵(karbutilate)、KUH-043(即,3-({[5-(二氟甲基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-基]甲基}磺酰基)-5,5-二甲基-4,5-二氢-1,2-噁唑)、ketospiradox、ketospiradox-potassium、乳氟禾草灵(lactofen)、lancotrione、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙基酯(MCPA-butotyl)、MCPA-丁基酯(MCPA-butyl)、MCPA-二甲基铵、MCPA-二乙醇胺(MCPA-diolamine)、MCPA-2-乙基己酯、MCPA-乙基酯(MCPA-ethyl)、MCPA-异丁基酯(MCPA-isobutyl)、MCPA-异辛基酯(MCPA-isoctyl)、MCPA-异丙基酯(MCPA-isopropyl)、MCPA-异丙基铵(MCPA-isopropylammonium)、MCPA-甲酯(MCPA-methyl)、MCPA-乙醇胺(MCPA-olamine)、MCPA-钾(MCPA-potassium)、MCPA-钠(MCPA-sodium)和MCPA-三乙醇胺(MCPA-trolamine)、MCPB、MCPB-甲酯(MCPB-methyl)、MCPB-乙酯(MCPB-ethyl)和MCPB-钠(MCPB-sodium)、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸丁氧基乙基酯(mecoprop-butotyl)、2-甲-4-氯丙酸二甲基铵(mecoprop-dimethylammonium)、2-甲-4-氯丙酸二乙醇胺(mecoprop-diolamine)、mecoprop-etexyl、mecoprop-ethadyl、2-甲-4-氯丙酸异辛酯(mecoprop-isoctyl)、2-甲-4-氯丙酸甲酯(mecoprop-methyl)、2-甲-4-氯丙酸钾(mecoprop-potassium)、2-甲-4-氯丙酸钠(mecoprop-sodium)和2-甲-4-氯丙酸三乙醇胺(mecoprop-trolamine)、精2-甲-4-氯丙酸(mecoprop-P)、精2-甲-4-氯丙酸丁氧基乙基酯(mecoprop-P-butotyl)、精-2-甲-4-氯丙酸二甲基铵(mecoprop-P-dimethylammonium)、精-2-甲-4-氯丙酸-2-乙基己酯(mecoprop-P-2-ethylhexyl)、精-2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidide)、氯磺酰草胺二乙醇胺(mefluidide-diolamine)、氯磺酰草胺钾(mefluidide-potassium)、二磺隆(mesosulfuron)、甲磺胺磺隆(mesosulfuron-methyl)、二磺隆钠盐(mesosulfuron-sodium salt)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、双醚氯吡嘧磺隆(metazosulfuron)、甲基苯噻隆(methabenzthiazuron)、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、异硫氰酸甲酯、溴谷隆(metobromuron)、异丙甲草胺(metolachlor)、精异丙甲草胺(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、嗪草酮(metribuzin)、磺隆(metsulfuron)、甲磺隆(metsulfuron-methyl)、禾草敌(molinate)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺甲酯(monosulfuron-methyl)、MT-5950(即,N-[3-氯-4-(1-甲基乙基)苯基]-2-甲基戊酰胺)、NGGC-011、敌草胺(napropamide))、NC-310(即4-(2,4-二氯苯甲酰基)-1-甲基-5-苄氧基吡唑)、NC-656(即3-[(异丙基磺酰基)甲基]-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)[1,2,4]三唑并-[4,3-a]吡啶-8-甲酰胺)、草不隆(neburon)、烟嘧磺隆(nicosulfuron)、壬酸(pelargonic acid)、氟草敏(norflurazon)、油酸(脂肪酸)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、氨磺乐灵(oryzalin)、丙炔噁草酮(oxadiargyl)、噁草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、二氯百草枯(paraquat dichloride)、百草枯硫酸二甲酯(paraquat-dimethylsulfate)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚、环戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、矿物油、苯敌草(phenmedipham)、苯敌草乙酯(phenmedipham-ethyl)、氨氯吡啶酸(picloram)、氨氯吡啶酸二甲基铵(picloram-dimethylammonium)、picloram-etexyl、氨氯吡啶酸异辛酯(picloram-isoctyl)、氨氯吡啶酸甲酯(picloram-methyl)、氨氯吡啶酸乙醇胺(picloram-olamine)、氨氯吡啶酸钾(picloram-potassium)、氨氯吡啶酸三乙基铵(picloram-triethylammonium)、picloram-tripromine、、氨氯吡啶酸三乙醇胺(picloram-trolamine)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron)、甲基氟嘧磺隆(primisulfuron-methyl)、氨氟乐灵(prodiamine)、环苯草酮(profoxydim)、扑灭通(prometon)、扑草净(prometryn)、毒草胺(propachlor)、敌稗(propanil)草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠盐(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamide)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、pyraflufen,吡草醚(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron)、吡嘧磺隆乙酯(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、pyribambenz、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、pyridafol、哒草特(pyridate)、环酯草醚(pyriftalid)、pyriminobac、嘧草醚(pyriminobac-methyl)、pyrimisulfan、pyrithiobac、嘧草硫醚(pyrithiobac-sodium)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、氯甲喹啉酸二甲基铵(quinclorac-dimethylammonium)、氯甲喹啉酸甲酯(quinclorac-methyl)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamine)、喹禾灵(quizalofop)、喹禾灵乙酯(quizalofop-ethyl)、精喹禾灵(quizalofop-P)、精喹禾灵乙酯(quizalofop-P-ethyl)、喹禾糠酯(quizalofop-P-tefuryl)、QYM201(即1-{2-氯-3-[(3-环丙基-5-羟基-1-甲基-1H-吡唑-4-基)羰基]-6-(三氟甲基)苯基}哌啶-2-酮)、砜嘧磺隆(rimsulfuron)、苯嘧磺草胺(saflufenacil)、烯禾啶(sethoxydim)、环草隆(siduron)、西玛津(simazine)、西草净(simetryn)、SL-261、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron)、甲嘧磺隆甲酯(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYP-249(即1-乙氧基-3-甲基-1-氧代丁-3-烯-2-基5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸酯)、SYP-300(即1-[7-氟-3-氧代-4-(丙-2-炔-1-基)-3,4-二氢-2H-1,4-苯并噁嗪-6-基]-3-丙基-2-硫代咪唑烷-4,5-二酮)、2,3,6-TBA、TCA(三氯乙酸)和其盐(如三氯乙酸铵、三氯乙酸钙、三氯乙酸乙酯、三氯乙酸镁、三氯乙酸钠)、丁噻隆(tebuthiuron)、特糠酯酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、特丁净(terbutryn)、四氟络草胺(tetflupyrolimet)、thaxtomin、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、thiencarbazone、噻酮磺隆(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron)、噻吩磺隆甲酯(thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、氟酮磺草胺(triafamone)、野燕畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆母酸(tribenuron)、苯磺隆甲酯(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、三氯吡氧乙酸丁氧基酯(triclopyr-butotyl)、三氯吡氧乙酸胆碱(triclopyr-choline)、三氯吡氧乙酸乙酯(triclopyr-ethyl)、三氯吡氧乙酸三乙基铵(triclopyr-triethylammonium)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠盐(trifloxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron)、氟胺磺隆甲酯(triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲(urea sulfate)、灭草敌(vernolate)、XDE-848、ZJ-0862(即3,4-二氯-N-{2-[(4,6-二甲氧基嘧啶-2-基)氧基]苄基}苯胺)、3-(2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢嘧啶-1-(2H)-基)苯基)-5-甲基-4,5-二氢异噁唑-5-甲酸乙酯、[(3-{2-氯-4-氟-5-[3-甲基-2,6-二氧代-4-(三氟甲基)-3,6-二氢嘧啶-1(2H)-基]苯氧基}吡啶-2-基)氧基]乙酸乙酯、3-氯-2-[3-(二氟甲基)异噁唑基-5-基]苯基5-氯嘧啶-2-基醚、2-(3,4-二甲氧基苯基)-4-[(2-羟基-6-氧代环己-1-烯-1-基)羰基]-6-甲基哒嗪-3(2H)-酮、2-({2-[(2-甲氧基乙氧基)甲基]-6-甲基吡啶-3-基}羰基)环己烷-1,3-二酮、(5-羟基-1-甲基-1H-吡唑-4-基)(3,3,4-三甲基-1,1-二氧化-2,3-二氢-1-苯并噻吩-5-基)甲酮、1-甲基-4-[(3,3,4-三甲基-1,1-二氧化-2,3-二氢-1-苯并噻吩-5-基)羰基]-1H-吡唑-5-基丙烷-1-磺酸酯、4-{2-氯-3-[(3,5-二甲基-1H-吡唑-1-基)甲基]-4-(甲基磺酰基)苯甲酰基}-1-甲基-1H-吡唑-5-基-1,3-二甲基-1H-吡唑-4-甲酸酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸氰基甲基酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丙-2-炔-1-基酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸苄基酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸乙酯、4-氨基-3-氯-5-氟-6-(7-氟-1-异丁酰基-1H-吲哚-6-基)吡啶-2-甲酸甲酯、6-(1-乙酰基-7-氟-1H-吲哚-6-基)-4-氨基-3-氯-5-氟吡啶-2-甲酸甲酯、4-氨基-3-氯-6-[1-(2,2-二甲基丙酰基)-7-氟-1H-吲哚-6-基]-5-氟吡啶-2-甲酸甲酯、4-氨基-3-氯-5-氟-6-[7-氟-1-(甲氧基乙酰基)-1H-吲哚-6-基]吡啶-2-甲酸甲酯、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸钾、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸钠、4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸丁酯、4-羟基-1-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑烷-2-酮、3-(5-叔丁基-1,2-噁唑-3-基)-4-羟基-1-甲基咪唑烷-2-酮、3-[5-氯-4-(三氟甲基)吡啶-2-基]-4-羟基-1-甲基咪唑烷-2-酮、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)吡啶-2-基]咪唑烷-2-酮、6-[(2-羟基-6-氧代环己-1-烯-1-基)羰基]-1,5-二甲基-3-(2-甲基苯基)喹唑啉-2,4(1H,3H)-二酮、3-(2,6-二甲基苯基)-6-[(2-羟基-6-氧代环己-1-烯-1-基)羰基]-1-甲基喹唑啉-2,4(1H,3H)-二酮、2-[2-氯-4-(甲基磺酰基)-3-(吗啉-4-基甲基)苯甲酰基]-3-羟基环己-2-烯-1-酮、1-(2-羧基乙基)-4-(嘧啶-2-基)哒嗪-1-鎓盐(具有阴离子,如氯离子、乙酸根或三氟乙酸根)、1-(2-羧基乙基)-4-(哒嗪-3-基)哒嗪-1-鎓盐(具有阴离子,如氯离子、乙酸根或三氟乙酸根)、4-(嘧啶-2-基)-1-(2-磺乙基)哒嗪-1-鎓盐(具有阴离子,如氯离子、乙酸根或三氟乙酸根)、4-(哒嗪-3-基)-1-(2-磺乙基)哒嗪-1-鎓盐(具有阴离子,如氯离子、乙酸根或三氟乙酸根)。
作为可能的混合配伍剂的植物生长调节剂的实例为:
脱落酸(abscisic acid)、阿拉酸式苯(acibenzolar)、阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、1-氨基环丙-1-基甲酸及其衍生物、5-氨基乙酰丙酸(5-)、环丙嘧啶醇(ancymidol)、6-苄基氨基嘌呤(6-benzylaminopurine)、bikinin、芸苔素内酯(brassinolide)、brassinolide-ethyl、儿茶酸(catechin)、壳寡糖(chitooligosaccharides)(CO;CO与LCO不同之处在于,它们缺少具有LCO特征的侧基脂肪酸链。CO有时也称为N-乙酰壳寡糖,同样由GlcNAc残基组成,但具有使它们与几丁质分子[(C8H13NO5)n,CAS编号1398-61-4]和壳聚糖分子[(C5H11NO4)n,CAS编号9012-76-4]不同的侧链修饰)、几丁质化合物、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酰胺酸(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆(dazomet)、dazomet-sodium、正癸醇、调呋酸(dikegulac)、调呋酸钠(dikegulac-sodium)、茵多酸(endothal)、茵多酸二钾(endothal-dipotassium)、茵多酸二钠(endothal-disodium)和单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、抑草丁(flurenol)、芴醇丁酯(flurenol-butyl)、芴醇甲酯(flurenol-methyl)、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉酸(gibberellic acid)、抗倒胺(inabenfide)、吲哚-3-乙酸(IAA)、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、烯丙苯噻唑(probenazole)、茉莉酸(jasmonic acid)、茉莉酸或其衍生物(如茉莉酸甲酯)、脂壳寡糖(Lipo-chitooligosaccharides)(LCO,有时也称为共生结瘤(Nod)信号(或Nod因子)或Myc因子,其由具有在非还原末端缩合的N-连接的脂肪酰基链的β-l,4-连接的N-乙酰基-D-葡糖胺(“GlcNAc”)残基的寡糖骨架组成。如本领域中所理解的,LCO的不同之处在于:骨架中GlcNAc残基的数量、脂肪酰基链的长度和饱和度以及还原和非还原糖残基的取代)、亚油酸或其衍生物、亚麻酸或其衍生物、马来酰肼、甲哌(mepiquat chloride)、mepiquatpentaborate、1-甲基环丙烯、3'-甲基脱落酸、2-(1-萘基)乙酰胺、1-萘基乙酸、2-萘氧基乙酸、硝基酚盐混合物(nitrophenolate mixture)、4-氧代-4[(2-苯乙基)氨基]丁酸、多效唑(paclobutrazol)、4-苯基丁酸、N-苯基邻氨甲酰苯甲酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmon)、水杨酸、水杨酸甲酯、独角金内酯(strigolacton)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、抗倒酯(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)、2-氟-N-(3-甲氧基苯基)-9H-嘌呤-6-胺。
本发明通式(I)的化合物的合适的结合物配伍剂还包括例如以下安全剂:
S1)来自杂环羧酸衍生物的化合物:
S1a)二氯苯基吡唑啉-3-羧酸类的化合物(S1a),优选以下化合物,如1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸、1-(2,4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-甲酸乙酯(S1-1)(“吡唑解草酯(mefenpyr-diethyl)”),以及相关化合物,如WO-A-91/07874中所记载;
S1b)二氯苯基吡唑羧酸的衍生物(S1b),优选化合物例如1-(2,4-二氯苯基)-5-甲基吡唑-3-甲酸乙酯(S1-2)、1-(2,4-二氯苯基)-5-异丙基吡唑-3-甲酸乙酯(S1-3)、1-(2,4-二氯苯基)-5-(1,1-二甲基乙基)吡唑-3-甲酸乙酯(S1-4)以及相关化合物,如EP-A-333131 131和EP-A-269 806中所记载;
S1c)1,5-二苯基吡唑-3-羧酸的衍生物(S1c),优选化合物例如1-(2,4-二氯苯基)-5-苯基吡唑-3-甲酸乙酯(S1-5)、1-(2-氯苯基)-5-苯基吡唑-3-甲酸甲酯(S1-6)以及相关化合物,如例如EP-A-268 554中所记载;
S1d)三唑羧酸类的化合物(S1d),优选化合物例如解草唑(乙酯),即1-(2,4-二氯苯基)-5-三氯甲基-(1H)-1,2,4-三唑-3-甲酸乙酯(S1-7),以及相关化合物,如EP-A-174562和EP-A-346620中所记载;
S1e)5-苄基-2-异噁唑啉-3-羧酸或5-苯基-2-异噁唑啉-3-羧酸的化合物或5,5-二苯基-2-异噁唑啉-3-羧酸类的化合物(S1e),优选化合物例如5-(2,4-二氯苄基)-2-异噁唑啉-3-甲酸乙酯(S1-8)或5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-9)以及相关化合物,如WO-A-91/08202中所记载,或者5,5-二苯基-2-异噁唑啉甲酸(S1-10)或5,5-二苯基-2-异噁唑啉-3-甲酸乙酯(S1-11)(“双苯噁唑酸(isoxadifen-ethyl)”)或5,5-二苯基-2-异噁唑啉-3-甲酸正丙酯(S1-12)或5-(4-氟苯基)-5-苯基-2-异噁唑啉-3-甲酸乙酯(S1-13),如专利申请WO-A-95/07897中所记载。
S2)来自8-喹啉氧基衍生物的化合物(S2):
S2a)8-喹啉氧基乙酸类的化合物(S2a),优选(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解毒喹(cloquintocet-mexyl)”)(S2-1),(5-氯-8-喹啉氧基)乙酸1,3-二甲基丁-1-基酯(S2-2),(5-氯-8-喹啉氧基)乙酸4-烯丙氧基丁酯(S2-3),(5-氯-8-喹啉氧基)乙酸1-烯丙氧基丙-2-基酯(S2-4),(5-氯-8-喹啉氧基)乙酸乙酯(S2-5),5-氯-8-喹啉氧基乙酸甲酯(S2-6),(5-氯-8-喹啉氧基)乙酸烯丙酯(S2-7),(5-氯-8-喹啉氧基)乙酸2-(2-亚丙基亚氨氧基)-1-乙酯(S2-8)、(5-氯-8-喹啉氧基)乙酸2-氧代丙-1-基酯(S2-9)以及相关化合物,如EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0 492 366中所记载,以及(5-氯-8-喹啉氧基)乙酸(S2-10)、其水合物及其盐,例如其锂盐、钠盐、钾盐、钙盐、镁盐、铝盐、铁盐、铵盐、季铵盐、锍盐或鏻盐,如WO-A-2002/34048中所记载;
S2b)(5-氯-8-喹啉氧基)丙二酸类的化合物(S2b),优选化合物例如(5-氯-8-喹啉氧基)丙二酸二乙酯、(5-氯-8-喹啉氧基)丙二酸二烯丙酯、(5-氯-8-喹啉氧基)丙二酸甲乙酯以及相关化合物,如EP-A-0 582 198中所记载。
S3)二氯乙酰胺类的活性化合物(S3),其经常用作苗前安全剂(作用于土壤的安全剂),例如
“二氯丙烯胺(dichlormid)”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1),
购自Stauffer的“R-29148”(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2),
购自Stauffer的“R-28725”(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3),
“解草嗪(benoxacor)”(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4),
购自PPG Industries的“PPG-1292”(N-烯丙基-N-[(1,3-二氧戊环-2-基)甲基]二氯乙酰胺)(S3-5),
购自Sagro-Chem的“DKA-24”(N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺)(S3-6),
购自Nitrokemia或Monsanto的“AD-67”或“MON 4660”(3-二氯乙酰基-1-氧杂-3-氮杂螺[4.5]癸烷)(S3-7),
购自TRI-Chemical RT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8),
购自BASF的“Diclonon”(Dicyclonon)或“BAS145138”或“LAB145138”((RS)-1-二氯乙酰基-3,3,8a-三甲基全氢吡咯并[1,2-a]嘧啶-6-酮)(S3-9),
“解草噁唑(furilazole)”或“MON 13900”((RS)-3-二氯乙酰基-5-(2-呋喃基)-2,2-二甲基噁唑烷)(S3-10),以及其(R)异构体(S3-11)。
S4)酰基磺酰胺类化合物(S4):
S4a)式(S4a)的N-酰基磺酰胺及其盐,如WO-A-97/45016中所记载,
其中
RA 1为(C1-C6)-烷基、(C3-C6)-环烷基,其中后2个基团被vA个选自以下的取代基取代:卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基,在环状基团的情况下,也被(C1-C4)-烷基和(C1-C4)-卤代烷基取代;
RA 2为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mA为1或2;
vA为0、1、2或3;
S4b)式(S4b)的4-(苯甲酰基氨磺酰基)苯甲酰胺类化合物及其盐,如WO-A-99/16744中所记载,
其中
RB 1、RB 2独立地为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RB 3为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基或(C1-C4)-烷氧基,
并且
mB为1或2,
例如以下那些,其中
RB 1=环丙基,RB 2=氢且(RB 3)=2-OMe(“环丙磺酰胺(cyprosulfamide)”,S4-1),
RB 1=环丙基,RB 2=氢且(RB 3)=5-Cl-2-OMe(S4-2),
RB 1=乙基,RB 2=氢且(RB 3)=2-OMe(S4-3),
RB 1=异丙基,RB 2=氢且(RB 3)=5-Cl-2-OMe(S4-4),和
RB 1=异丙基,RB 2=氢且(RB 3)=2-OMe(S4-5);
S4c)式(S4c)的苯甲酰基氨磺酰基苯基脲类的化合物,如EP-A-365484中所记载,
其中
RC 1、RC 2独立地为氢、(C1-C8)-烷基、(C3-C8)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RC 3为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3,并且
mC为1或2;
例如
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3-甲基脲,
1-[4-(N-2-甲氧基苯甲酰基氨磺酰基)苯基]-3,3-二甲基脲,
1-[4-(N-4,5-二甲基苯甲酰基氨磺酰基)苯基]-3-甲基脲;
S4d)式(S4d)的N-苯基磺酰基对苯二甲酰胺类的化合物及其盐,其例如由CN101838227已知,
其中
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
RD 5为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C5-C6)-环烯基。
S5)来自羟基芳族化合物和芳族-脂族羧酸衍生物类的活性化合物(S5),例如3,4,5-三乙酰氧基苯甲酸乙酯、3,5-二甲氧基-4-羟基苯甲酸、3,5-二羟基苯甲酸、4-羟基水杨酸、4-氟水杨酸、2-羟基肉桂酸、2,4-二氯肉桂酸,如WO-A-2004/084631、WO-A-2005/015994、WO-A-2005/016001中所记载。
S6)来自1,2-二氢喹喔啉-2-酮类的活性化合物(S6),例如1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮、1-甲基-3-(2-噻吩基)-1,2-二氢喹喔啉-2-硫酮、1-(2-氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮盐酸盐、1-(2-甲基磺酰基氨基乙基)-3-(2-噻吩基)-1,2-二氢喹喔啉-2-酮,如WO-A-2005/112630中所记载。
S7)来自二苯基甲氧基乙酸衍生物类别的化合物(S7),例如二苯基甲氧基乙酸甲酯(CAS登记号41858-19-9)(S7-1),二苯基甲氧基乙酸乙酯或二苯基甲氧基乙酸,如WO-A-98/38856中所记载。
S8)式(S8)的化合物,如WO-A-98/27049中所记载,
其中符号和下标定义如下:
RD 1为卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基,
RD 2为氢或(C1-C4)-烷基,
RD 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳的基团各自为未取代的或被一个或多个、优选最高达三个相同或不同的选自卤素和烷氧基的基团取代,
nD为0至2的整数。
S9)来自3-(5-四唑基羰基)-2-喹诺酮类的活性化合物(S9),例如1,2-二氢-4-羟基-1-乙基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号219479-18-2)、1,2-二氢-4-羟基-1-甲基-3-(5-四唑基羰基)-2-喹诺酮(CAS登记号95855-00-8),如WO-A-199/000020中所记载。
S10)式(S10a)或(S10b)的化合物
如WO-A-2007/023719和WO-A-2007/023764中所记载,
其中
RE 1为卤素、(C1-C4)-烷基、甲氧基、硝基、氰基、CF3、OCF3,
YE、ZE独立地为O或S,
nE为0至4的整数,
RE 2为(C1-C16)-烷基、(C2-C6)-烯基、(C3-C6)-环烷基、芳基、苄基、卤代苄基,
RE 3为氢或(C1-C6)-烷基。
S11)氧亚氨基化合物类的活性化合物(S11),其已知为拌种剂,例如“解草腈(oxabetrinil)”((Z)-1,3-二氧戊环-2-基甲氧基亚氨基(苯基)乙腈)(S11-1),其已知为用于粟/高粱抵抗异丙甲草胺损害的拌种安全剂,
“氟草肟(fluxofenim)”(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧戊环-2-基甲基)肟)(S11-2),其已知为用于粟/高粱抵抗异丙甲草胺损害的拌种安全剂,以及
“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知为用于粟/高粱抵抗异丙甲草胺损害的拌种安全剂。
S12)来自异硫代苯并二氢吡喃酮(isothiochromanones)类的活性化合物(S12),例如[(3-氧代-1H-2-苯并硫代吡喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登记号205121-04-6)(S12-1),以及WO-A-1998/13361中的相关化合物。
S13)一种或多种来自组(S13)的化合物:
“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知为用于玉米抵抗硫代氨基甲酸酯除草剂损害的拌种安全剂,
“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知为在播种的稻中用于丙草胺的安全剂,
“解草胺(flurazole)”(2-氯-4-三氟甲基-1,3-噻唑-5-甲酸苄酯)(S13-3),其已知为用于粟/高粱抵抗甲草胺和异丙甲草胺损害的拌种安全剂,
购自American Cyanamid的“CL 304415”(CAS登记号31541-57-8)(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知为用于玉米抵抗咪唑啉酮损害的安全剂,
购自Nitrokemia的“MG 191”(CAS登记号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧戊环)(S13-5),其已知为用于玉米的安全剂,
购自Nitrokemia的“MG 838”(CAS登记号133993-74-5)(1-氧杂-4-氮杂螺[4.5]癸烷-4-二硫代甲酸2-丙烯基酯)(S13-6),“乙拌磷(disulfoton)”(二硫代磷酸O,O-二乙基S-2-乙硫基乙基酯)(S13-7),
“增效磷(dietholate)”(硫代磷酸O,O-二乙基O-苯基酯)(S13-8),“mephenate”(甲基氨基甲酸4-氯苯酯)(S13-9)。
S14)除了对杂草具有除草作用外,还对作物植物如稻具有安全剂作用的活性化合物,例如
“哌草丹”或“MY-93”(1-苯基乙基哌啶-1-硫代甲酸S-1-甲酯),其已知为用于稻抵抗除草剂禾草敌损害的安全剂,
“杀草隆”或“SK 23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知为用于稻抵抗唑吡嘧磺隆除草剂损害的安全剂,
“苄草隆”=“JC-940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲,参见JP-A-60087254),其已知为用于稻抵抗一些除草剂损害的安全剂,
“苯草酮(methoxyphenone)”或“NK 049”(3,3'-二甲基-4-甲氧基二苯甲酮),其已知为用于稻抵抗一些除草剂损害的安全剂,
购自Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯)(CAS登记号54091-06-4),其已知为用于在稻中抵抗一些除草剂损害的安全剂。
S15)式(S15)的化合物或其互变异构体
如WO-A-2008/131861和WO-A-2008/131860中所记载的,
其中
RH 1为(C1-C6)-卤代烷基,
RH 2为氢或卤素,并且
RH 3、RH 4各自独立地为氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中后3个基团中的每一个均为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基、(C1-C4)-烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)-卤代烷氧基]羰基、未取代的或被取代的(C3-C6)-环烷基、未取代的或被取代的苯基和未取代的或被取代的杂环基,或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧上稠合至4元至6元饱和或不饱和的碳环的(C3-C6)-环烷基,或在环的一侧上稠合至4元至6元饱和或不饱和的碳环的(C4-C6)-环烯基,
其中后4个基团中每一个均为未取代的或被一个或多个选自以下的基团取代:卤素、羟基、氰基、(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)烷基氨基、二[(C1-C4)-烷基]氨基、[(C1-C4)-烷氧基]羰基、[(C1-C4)卤代烷氧基]羰基、未取代的或被取代的(C3-C6)-环烷基、未取代的或被取代的苯基和未取代的或被取代的杂环基,
或者
RH 3为(C1-C4)-烷氧基、(C2-C4)-烯氧基、(C2-C6)-炔氧基或(C2-C4)-卤代烷氧基,并且
RH 4为氢或(C1-C4)-烷基,或
RH 3和RH 4与直接键合的氮原子一起形成四元至八元杂环,所述杂环除了氮原子外还可包含其他环杂原子,优选最高达两个选自N、O和S的其他环杂原子,并且所述杂环为未取代的或被一个或多个选自以下的基团取代:卤素、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)卤代烷氧基和(C1-C4)-烷硫基。
S16)主要用作除草剂但还对作物植物具有安全剂作用的活性化合物,
例如
(2,4-二氯苯氧基)乙酸(2,4-D),
(4-氯苯氧基)乙酸,
(R,S)-2-(4-氯-邻甲苯氧基)丙酸(mecoprop),
4-(2,4-二氯苯氧基)丁酸(2,4-DB),
(4-氯-邻甲苯氧基)乙酸(MCPA),
4-(4-氯-邻甲苯氧基)丁酸,
4-(4-氯苯氧基)丁酸,
3,6-二氯-2-甲氧基苯甲酸(麦草畏),
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
与本发明通式(I)的化合物和/或其盐和N-氧化物、特别是与式(I-001)至(I-027)的化合物、其盐或N-氧化物结合的优选安全剂为解毒喹、环丙磺酰胺、解草唑、双苯噁唑酸、吡唑解草酯、解草啶、苄草隆、S4-1和S4-5,特别优选的安全剂为:解毒喹、环丙磺酰胺、双苯噁唑酸和吡唑解草酯。
生物实施例:
实施例和下表中使用以下缩写:
测试的有害植物:
ABUTH:苘麻(Abutilon theophrasti)
ALOMY:大穗看麦娘(Alopecurus myosuroides)
AMARE反枝苋(Amaranthus retroflexus)
DIGSA:马唐(Digitaria sanguinalis)
ECHCG:稗草(Echinochloa crus-galli)
KCHSC:地肤(Kochia scoparia)
LOLRI瑞士黑麦草(Lolium rigidum)
MATIN:无香母菊(Matricaria inodora)
POAAN:早熟禾(Poa annua)
SETVI:狗尾草(Setaria viridis)
STEME:繁缕(Stellaria media)
VERPE:阿拉伯婆婆纳(Veronica persica)
A.苗前除草作用
将单子叶杂草植物和双子叶杂草植物的种子播种在塑料盆中(每盆用一种单子叶杂草植物和一种双子叶杂草植物双播种)的砂质壤土中并用土壤覆盖。将配制成可湿性粉剂(WP)或乳油(EC)形式的本发明化合物,在添加0.5%添加剂的情况下,在每公顷600升水的施用率(经转换)下,以水性悬浮液或乳液的形式施用至覆盖土壤的表面。在处理后,将盆置于温室中并保持在测试植物的最佳生长条件下。在约3周后,与未处理的对照相比,对测试植物的损害进行目测分级(除草效果以百分比(%)计:100%效果=植物已经死亡,0%效果=如同对照植物)
下表A1至A12显示了根据表1的所选的通式(I)的化合物对各种有害植物的效果以及在通过上述实验方法步骤获得的对应于1280g/ha的施用率下。
表A1
实施例编号 | 剂量[g/ha] | ALOMY |
I-009 | 1280 | 100 |
表A2
实施例编号 | 剂量[g/ha] | ECHCG |
I-009 | 1280 | 90 |
表A3
实施例编号 | 剂量[g/ha] | KCHSC |
I-002 | 1280 | 90 |
I-005 | 1280 | 100 |
I-009 | 1280 | 100 |
I-015 | 1280 | 90 |
I-025 | 1280 | 90 |
表A4
实施例编号 | 剂量[g/ha] | LOLRI |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-004 | 1280 | 100 |
I-005 | 1280 | 100 |
I-009 | 1280 | 90 |
I-010 | 1280 | 100 |
I-021 | 1280 | 100 |
I-025 | 1280 | 100 |
I-026 | 1280 | 100 |
表A5
实施例编号 | 剂量[g/ha] | MATIN |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-003 | 1280 | 100 |
I-004 | 1280 | 90 |
I-005 | 1280 | 100 |
I-009 | 1280 | 100 |
I-010 | 1280 | 100 |
I-011 | 1280 | 90 |
I-020 | 1280 | 90 |
I-021 | 1280 | 100 |
I-023 | 1280 | 100 |
I-024 | 1280 | 90 |
I-025 | 1280 | 100 |
I-026 | 1280 | 100 |
表A6
实施例编号 | 剂量[g/ha] | SETVI |
I-001 | 1280 | 90 |
I-009 | 1280 | 90 |
I-025 | 1280 | 90 |
表A7
实施例编号 | 剂量[g/ha] | STEME |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-003 | 1280 | 100 |
I-004 | 1280 | 100 |
I-005 | 1280 | 100 |
I-008 | 1280 | 90 |
I-009 | 1280 | 100 |
I-010 | 1280 | 90 |
I-011 | 1280 | 90 |
I-020 | 1280 | 100 |
I-021 | 1280 | 100 |
I-022 | 1280 | 100 |
I-023 | 1280 | 90 |
I-025 | 1280 | 90 |
I-026 | 1280 | 100 |
I-027 | 1280 | 90 |
表A8
实施例编号 | 剂量[g/ha] | VERPE |
I-002 | 1280 | 100 |
I-003 | 1280 | 90 |
I-009 | 1280 | 90 |
I-021 | 1280 | 90 |
表A9
表A10
实施例编号 | 剂量[g/ha] | AMARE |
I-001 | 1280 | 100 |
I-002 | 1280 | 90 |
I-003 | 1280 | 100 |
I-004 | 1280 | 90 |
I-005 | 1280 | 100 |
I-008 | 1280 | 90 |
I-009 | 1280 | 100 |
I-011 | 1280 | 100 |
I-013 | 1280 | 100 |
I-020 | 1280 | 90 |
I-021 | 1280 | 100 |
I-023 | 1280 | 90 |
I-025 | 1280 | 100 |
I-026 | 1280 | 100 |
表A11
实施例编号 | 剂量[g/ha] | ABUTH |
I-025 | 1280 | 100 |
表A12
实施例编号 | 剂量[g/ha] | DIGSA |
I-005 | 1280 | 90 |
结果表明,在1280g的活性成分/公顷的施用率下,本发明通式(I)的各种化合物对广谱的有害单子叶植物和双子叶植物(如苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、马唐(DIGSA)、稗草(ECHCG)、地肤(KCHSC)、瑞士黑麦草(LOLRI)、无香母菊(MATIN)、早熟禾(POAAN)、狗尾草(SETVI)、繁缕(STEME)和阿拉伯婆婆纳(VERPE))具有非常好的苗前除草功效。
B.苗后除草作用
将单子叶杂草植物和双子叶杂草植物的种子播种在塑料盆中(每盆用一种单子叶杂草植物和一种双子叶杂草植物双播种)的砂质壤土中并用土壤覆盖,并在受控的生长条件下生长。在播种2至3周后,在单叶阶段喷洒测试植物。将配制成可湿性粉剂(WP)或乳油(EC)形式的本发明化合物,在添加0.5%添加剂的情况下,在每公顷600L水的施用率(经转换)下,以水性悬浮液或乳液的形式喷洒至绿色植物部位上。将测试植物置于温室中并在最佳生长条件下保持约3周,然后与未处理的对照相比较,目测评估所述制剂的效果(除草效果以百分比(%)计:100%效果=植物已经死亡,0%效果=如同对照植物)。
下表B1至B11显示了根据表1的所选的通式(I)的化合物在使用通过上文提及的实验方法步骤获得的对应于1280g/ha的施用率的情况下对各种有害植物的效果。
表B1
实施例编号 | 剂量[g/ha] | ABUTH |
I-002 | 1280 | 90 |
I-009 | 1280 | 90 |
I-013 | 1280 | 100 |
I-021 | 1280 | 100 |
表B2
实施例编号 | 剂量[g/ha] | ALOMY |
I-002 | 1280 | 100 |
I-008 | 1280 | 90 |
I-009 | 1280 | 100 |
表B3
实施例编号 | 剂量[g/ha] | KCHSC |
I-002 | 1280 | 100 |
I-005 | 1280 | 90 |
I-009 | 1280 | 100 |
I-010 | 1280 | 100 |
I-013 | 1280 | 100 |
I-014 | 1280 | 90 |
I-015 | 1280 | 90 |
I-021 | 1280 | 100 |
I-026 | 1280 | 90 |
表B4
实施例编号 | 剂量[g/ha] | LOLRI |
I-001 | 1280 | 90 |
I-002 | 1280 | 100 |
I-009 | 1280 | 90 |
I-021 | 1280 | 90 |
I-025 | 1280 | 90 |
表B5
实施例编号 | 剂量[g/ha] | MATIN |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-009 | 1280 | 100 |
I-013 | 1280 | 100 |
I-014 | 1280 | 100 |
I-015 | 1280 | 100 |
I-020 | 1280 | 90 |
I-021 | 1280 | 100 |
I-024 | 1280 | 100 |
I-025 | 1280 | 90 |
表B6
实施例编号 | 剂量[g/ha] | SETVI |
I-002 | 1280 | 90 |
I-009 | 1280 | 90 |
I-015 | 1280 | 90 |
表B7
实施例编号 | 剂量[g/ha] | STEME |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-003 | 1280 | 90 |
I-005 | 1280 | 90 |
I-008 | 1280 | 100 |
I-009 | 1280 | 100 |
I-013 | 1280 | 100 |
I-014 | 1280 | 100 |
I-015 | 1280 | 100 |
I-020 | 1280 | 90 |
I-021 | 1280 | 100 |
I-022 | 1280 | 90 |
I-025 | 1280 | 90 |
I-026 | 1280 | 100 |
表B8
实施例编号 | 剂量[g/ha] | VERPE |
I-002 | 1280 | 100 |
I-003 | 1280 | 100 |
I-004 | 1280 | 100 |
I-005 | 1280 | 100 |
I-008 | 1280 | 90 |
I-009 | 1280 | 100 |
I-010 | 1280 | 100 |
I-013 | 1280 | 100 |
I-014 | 1280 | 100 |
I-015 | 1280 | 90 |
I-020 | 1280 | 100 |
I-021 | 1280 | 100 |
I-024 | 1280 | 90 |
I-025 | 1280 | 90 |
I-026 | 1280 | 90 |
表B9
实施例编号 | 剂量[g/ha] | POAAN |
I-001 | 1280 | 100 |
I-002 | 1280 | 100 |
I-004 | 1280 | 100 |
I-005 | 1280 | 100 |
I-009 | 1280 | 100 |
I-010 | 1280 | 90 |
I-021 | 1280 | 100 |
表B10
实施例编号 | 剂量[g/ha] | AMARE |
I-001 | 1280 | 90 |
I-002 | 1280 | 100 |
I-003 | 1280 | 90 |
I-004 | 1280 | 100 |
I-008 | 1280 | 100 |
I-009 | 1280 | 100 |
I-010 | 1280 | 100 |
I-013 | 1280 | 100 |
I-014 | 1280 | 100 |
I-015 | 1280 | 100 |
I-020 | 1280 | 90 |
I-021 | 1280 | 100 |
I-022 | 1280 | 90 |
I-023 | 1280 | 90 |
I-024 | 1280 | 90 |
I-025 | 1280 | 100 |
I-026 | 1280 | 100 |
表B11
实施例编号 | 剂量[g/ha] | ECHCG |
I-025 | 1280 | 90 |
结果表明,在1280g的活性成分/公顷的施用率下,本发明通式(I)的各种化合物对广谱的有害单子叶植物和双子叶植物(如苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、稗草(ECHCG)、地肤(KCHSC)、瑞士黑麦草(LOLRI)、无香母菊(MATIN)、早熟禾(POAAN)、狗尾草(SETVI)、繁缕(STEME)和阿拉伯婆婆纳(VERPE))具有极好的苗后除草效果。
C.苗前除草作用
将单子叶杂草植物和双子叶杂草植物的种子播种在塑料盆中(每盆用一种单子叶杂草和一种双子叶杂草双播种)的砂质壤土中并用土壤覆盖。将配制成可湿性粉剂(WP)或乳油(EC)形式的本发明化合物,在添加0.5%添加剂的情况下,在每公顷600升水的施用率(经转换)下,以水性悬浮液或乳液的形式施用至覆盖土壤的表面。在处理后,将盆置于温室中并保持在测试植物的最佳生长条件下。在约3周后,与未处理的对照相比较,对测试植物的损害进行目测分级(除草效果以百分比(%)计:100%效果=植物已经死亡,0%效果=如同对照植物)
下表C1至C7显示了根据表1的所选的通式(I)的化合物在使用通过上述实验方法步骤获得的对应于320g/ha的施用率的情况下对各种有害植物的效果。
表C1
实施例编号 | 剂量[g/ha] | KCHSC |
I-009 | 320 | 90 |
表C2
实施例编号 | 剂量[g/ha] | LOLRI |
I-002 | 320 | 100 |
I-021 | 320 | 90 |
I-025 | 320 | 90 |
表C3
表C4
实施例编号 | 剂量[g/ha] | STEME |
I-001 | 320 | 100 |
I-002 | 320 | 100 |
I-005 | 320 | 100 |
I-009 | 320 | 100 |
I-011 | 320 | 90 |
I-020 | 320 | 90 |
I-021 | 320 | 90 |
I-025 | 320 | 90 |
I-026 | 320 | 90 |
表C5
实施例编号 | 剂量[g/ha] | VERPE |
I-002 | 320 | 90 |
表C6
实施例编号 | 剂量[g/ha] | POAAN |
I-001 | 320 | 100 |
I-002 | 320 | 100 |
I-005 | 320 | 100 |
I-011 | 320 | 90 |
I-021 | 320 | 90 |
表C7
实施例编号 | 剂量[g/ha] | AMARE |
I-001 | 320 | 100 |
I-009 | 320 | 90 |
I-025 | 320 | 90 |
结果表明,在320g的活性成分/公顷的施用率下,本发明通式(I)的各种化合物对广谱的有害单子叶植物和双子叶植物(如反枝苋(AMARE)、地肤(KCHSC)、瑞士黑麦草(LOLRI)、无香母菊(MATIN)、早熟禾(POAAN)、繁缕(STEME)和阿拉伯婆婆纳(VERPE))具有非常好的苗前除草功效。
D.苗后除草作用
将单子叶杂草植物和双子叶杂草植物的种子播种在塑料盆中(每盆用一种单子叶杂草植物和一种双子叶杂草植物双播种)的砂质壤土中,用土壤覆盖,并在受控的生长条件下生长。在播种2至3周后,在单叶阶段喷洒测试植物。将配制成可湿性粉剂(WP)或乳油(EC)形式的本发明化合物,在添加0.5%添加剂的情况下,在每公顷600L水的施用率(经转换)下,以水性悬浮液或乳液的形式喷洒至绿色植物部位。将测试植物置于温室中并在最佳生长条件下保持约3周,然后,与未处理的对照相比较,目测评估所述制剂的效果(除草效果以百分比(%)计:100%效果=植物已经死亡,0%效果=如同对照植物)。
下表D1至D9显示了根据表1的所选的通式(I)的化合物在使用通过上述实验方法步骤获得的对应于320g/ha的施用率的情况下对各种有害植物的效果。
表D1
实施例编号 | 剂量[g/ha] | ALOMY |
I-002 | 320 | 100 |
I-009 | 320 | 90 |
表D2
实施例编号 | 剂量[g/ha] | KCHSC |
I-002 | 320 | 100 |
I-009 | 320 | 100 |
I-021 | 320 | 90 |
表D3
实施例编号 | 剂量[g/ha] | LOLRI |
I-002 | 320 | 90 |
表D4
实施例编号 | 剂量[g/ha] | MATIN |
I-001 | 320 | 90 |
I-002 | 320 | 90 |
I-009 | 320 | 100 |
I-013 | 320 | 100 |
I-015 | 320 | 90 |
I-021 | 320 | 100 |
I-024 | 320 | 90 |
表D5
实施例编号 | 剂量[g/ha] | STEME |
I-001 | 320 | 100 |
I-002 | 320 | 100 |
I-005 | 320 | 90 |
I-008 | 320 | 90 |
I-009 | 320 | 100 |
I-014 | 320 | 90 |
I-015 | 320 | 100 |
I-021 | 320 | 90 |
I-025 | 320 | 90 |
表D6
表D7
实施例编号 | 剂量[g/ha] | POAAN |
I-001 | 320 | 100 |
I-002 | 320 | 100 |
I-005 | 320 | 100 |
I-009 | 320 | 90 |
I-010 | 320 | 90 |
表D8
实施例编号 | 剂量[g/ha] | AMARE |
I-003 | 320 | 90 |
I-009 | 320 | 100 |
I-010 | 320 | 100 |
I-013 | 320 | 90 |
I-021 | 320 | 100 |
I-025 | 320 | 90 |
I-026 | 320 | 90 |
表D9
实施例编号 | 剂量[g/ha] | ABUTH |
I-021 | 320 | 90 |
结果表明,在320g的活性成分/公顷的施用率下,本发明通式(I)的各种化合物对广谱的有害单子叶植物和双子叶植物(如苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、地肤(KCHSC)、瑞士黑麦草(LOLRI)、无香母菊(MATIN)、早熟禾(POAAN)、繁缕(STEME)和阿拉伯婆婆纳(VERPE))具有极好的苗后除草功效。
Claims (8)
1.通式(I)的取代的1,2,4-噻二唑基烟酰胺和/或其盐或N-氧化物
其中
W表示氧或硫,
R1表示氢、卤素、氰基、(C1-C3)-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)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷硫基、(C1-C4)-卤代烷基亚磺酰基或(C1-C4)-卤代烷基磺酰基,
R2表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3表示氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基,
R4表示氢、卤素、氰基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基,
R5表示氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C3-C6)-卤代环烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基。
2.根据权利要求1所述的通式(I)的化合物和/或其盐或N-氧化物,其特征在于,
W表示氧或硫,
R1表示氢、卤素、(C1-C3)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基或(C1-C4)-卤代烷硫基,
R2表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3表示氢、卤素、(C1-C4)-烷基或(C1-C4)-卤代烷基,
R4表示氢、卤素或(C1-C4)-卤代烷基,
R5表示氢、卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、
(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基。
3.根据权利要求1所述的通式(I)的化合物和/或其盐或N-氧化物,其特征在于,
W表示氧或硫,优选氧,
R1表示氢、卤素、(C1-C3)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-烷硫基,
R2表示(C1-C4)-烷基或(C1-C4)-卤代烷基,
R3表示氢,
R4表示氢或卤素,
R5表示氢、卤素、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基。
4.根据权利要求1所述的通式(I)的化合物和/或其盐或N-氧化物,其特征在于,
W表示氧,
R1表示氢、氯、溴、甲基、乙基、三氟甲基、三氯甲基、甲氧基或甲基磺酰基,
R2表示甲基、乙基、异丙基、二氟甲基或三氟甲基,
R3表示氢,
R4表示氢、氟或氯,
R5表示氢、氟、氯、溴、二氟甲基、环丙基或甲氧基。
5.根据权利要求1所述的通式(I)的化合物和/或其盐或N-氧化物,其特征在于,
W表示氧,
R1表示氢、氯、溴、甲基或三氟甲基,
R2表示甲基、乙基、异丙基或三氟甲基,
R3表示氢,
R4表示氢、氟或氯,
R5表示氢、氟、氯、溴、甲氧基或环丙基。
6.一种或多种如权利要求1至5中任一项所定义的通式(I)的化合物和/或其盐或N-氧化物作为除草剂和/或植物生长调节剂的用途。
7.除草的和/或植物生长调节的组合物,其特征在于,所述组合物包含一种或多种如权利要求1至5中任一项所定义的式(I)的化合物和/或其盐或N-氧化物,和一种或多种选自组(i)和/或(ii)的其他物质,其中
(i)一种或多种其他农用化学活性物质,其选自杀昆虫剂、杀螨剂、杀线虫剂、其他除草剂、杀真菌剂、安全剂、肥料和/或其他生长调节剂,
(ii)一种或多种作物保护中常规的制剂助剂。
8.一种用于防治有害植物或用于调节植物生长的方法,其特征在于,将有效量的以下物质:
-一种或多种如权利要求1至5中任一项所定义的式(I)的化合物和/或其盐或N-氧化物,或
-如权利要求7所述的组合物,
施用至植物、植物的种子、植物生长于其中或其上的土壤或栽培区域。
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-
2022
- 2022-08-12 CN CN202280054477.0A patent/CN117794928A/zh active Pending
- 2022-08-12 MX MX2024002082A patent/MX2024002082A/es unknown
- 2022-08-12 EP EP22764751.8A patent/EP4387969A1/en active Pending
- 2022-08-12 AU AU2022329086A patent/AU2022329086A1/en active Pending
- 2022-08-12 WO PCT/EP2022/072676 patent/WO2023020963A1/en active Application Filing
- 2022-08-12 CA CA3229298A patent/CA3229298A1/en active Pending
- 2022-08-16 AR ARP220102202A patent/AR126799A1/es unknown
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CA3229298A1 (en) | 2023-02-23 |
MX2024002082A (es) | 2024-03-05 |
EP4387969A1 (en) | 2024-06-26 |
AR126799A1 (es) | 2023-11-15 |
WO2023020963A1 (en) | 2023-02-23 |
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