CN115996919A - 取代的杂芳基氧基吡啶、其盐及它们作为除草剂的用途 - Google Patents
取代的杂芳基氧基吡啶、其盐及它们作为除草剂的用途 Download PDFInfo
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- CN115996919A CN115996919A CN202180046376.4A CN202180046376A CN115996919A CN 115996919 A CN115996919 A CN 115996919A CN 202180046376 A CN202180046376 A CN 202180046376A CN 115996919 A CN115996919 A CN 115996919A
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- Prior art keywords
- alkyl
- group
- cycloalkyl
- cyano
- methyl
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- 238000000034 method Methods 0.000 claims description 35
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- 125000001424 substituent group Chemical group 0.000 claims description 13
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- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
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- JGMJQSFLQWGYMQ-UHFFFAOYSA-M sodium;2,6-dichloro-n-phenylaniline;acetate Chemical compound [Na+].CC([O-])=O.ClC1=CC=CC(Cl)=C1NC1=CC=CC=C1 JGMJQSFLQWGYMQ-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- YWICANUUQPYHOW-UHFFFAOYSA-M sodium;2-(phosphonomethylamino)acetate Chemical compound [Na+].OP(O)(=O)CNCC([O-])=O YWICANUUQPYHOW-UHFFFAOYSA-M 0.000 description 1
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- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- YPMAQKXGDCKXPE-WCCKRBBISA-M sodium;[(3s)-3-amino-3-carboxypropyl]-methylphosphinate Chemical compound [Na+].CP([O-])(=O)CC[C@H](N)C(O)=O YPMAQKXGDCKXPE-WCCKRBBISA-M 0.000 description 1
- UPDATVKGFTVGQJ-UHFFFAOYSA-N sodium;azane Chemical compound N.[Na+] UPDATVKGFTVGQJ-UHFFFAOYSA-N 0.000 description 1
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- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DFFWZNDCNBOKDI-UHFFFAOYSA-N trinexapac Chemical compound O=C1CC(C(=O)O)CC(=O)C1=C(O)C1CC1 DFFWZNDCNBOKDI-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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- 238000001238 wet grinding Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本发明涉及通式(I)的取代的杂芳基氧基吡啶,涉及它们作为除草剂,特别是作为用于防治在栽培植物作物中的杂草和/或禾本科杂草的除草剂,和/或作为用于影响栽培植物作物生长的植物生长调节剂的用途。本发明还涉及包含一种或多种通式(I)的化合物的除草剂和/或植物生长防治剂。
Description
本发明涉及作物保护产品的技术领域,特别是涉及用于选择性防治有用植物作物中的阔叶杂草和禾本科杂草的除草剂的技术领域。
具体地,本发明涉及取代的杂芳基氧基吡啶及其盐、其制备方法及其作为除草剂的用途。
在它们的应用中,迄今已知的用于选择性防治有用植物作物中的有害植物的作物保护产品或用于防治不想要的植物的活性成分有时具有缺点,(a)它们对特定的有害植物是否具有不充分的除草活性(如果有的话),(b)可用活性成分防治的有害植物的谱是否不足够宽,(c)它们在有用植物作物中的选择性是否太低和/或(d)它们是否具有毒理学上不利的性质。此外,一些可用作许多有用植物的植物生长调节剂的活性成分在其他有用植物中引起不想要的采收量降低,或(如果有的话)仅在窄的施用率范围内与作物植物相容。由于前体和试剂难以获得,一些已知的活性成分不能以工业规模经济地制备,或其仅具有不充分的化学稳定性。在其他活性成分的情况下,活性过高地依赖环境条件,例如气候条件和土壤条件。
这些已知化合物的除草作用、尤其是在低施用率下的除草作用,和/或其与作物植物的相容性仍然需要改进。
WO 2016/149315记载了多种3-嘧啶基氧基吡啶作为除草剂。
WO 2020/002089记载了多种具有除草作用的2-杂芳基氧基吡啶,其在吡啶的3位带有通过1-原子桥键合至吡啶的环作为取代基。
WO 2004/035564记载了多种作为除草剂的2-杂芳基氧基吡啶,其在吡啶的3位被吡唑基取代。相比之下,对于在吡啶的3位被其他5元杂环取代的2-杂芳基氧基吡啶及其盐类,尚无记载。
出人意料地,现已发现特定的2-杂芳基氧基吡啶和/或其盐特别适合作为活性除草成分。
因此,本发明提供通式(I)的取代的杂芳基氧基吡啶或其盐
其中
R1为任选取代的5元杂芳基环,其任选被最高达3个独立地选自R4的取代基取代,
R2独立地为卤素、羟基、氨基、氰基、硝基、甲酰基、甲酰胺、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-C4)-卤代烯基、(C2-C4)-卤代炔基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷氧基、(C1-C4)-烯氧基、(C1-C4)-炔氧基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C3-C6)-环烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C3-C6)-环烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C3-C6)-环烷基磺酰基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C3-C6)-环烷基羰基、羧基、(C1-C4)-烷氧基羰基、(C1-C4)-卤代烷氧基羰基、(C3-C6)-环烷氧基羰基、(C1-C4)-烷基氨基羰基、(C2-C6)-二烷基氨基羰基、(C3-C6)-环烷基氨基羰基、(C1-C4)-烷基羰基氨基、(C1-C4)-卤代烷基羰基氨基、(C2-C6)-环烷基羰基氨基、(C1-C4)-烷氧基羰基氨基、(C1-C4)-烷基氨基羰基氨基、(C2-C6)-二烷基氨基羰基氨基、羧基-(C1-C4)-烷基、(C1-C4)-烷氧基羰基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基羰基-(C1-C4)-烷基、(C3-C6)-环烷氧基羰基-(C1-C4)-烷基、(C1-C4)-烷基氨基磺酰基、(C2-C6)-二烷基氨基磺酰基或(C3-C6)-三烷基甲硅烷基,
n为0、1、2或3,
R3为卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,
R4为氢、卤素、羟基、氨基、氰基、甲酰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C4)-烷基、(C1-C4)-烷基-(C3-C6)-环烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、卤素或氰基,
不包括其中R1为未取代的或取代的3-吡唑的化合物。
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(piperidino)、吗啉基(morpholino)或吡啶基(pyridino)。然后,这些盐包含酸的共轭碱作为阴离子。合适的去质子化形式的取代基(例如磺酸,特别是磺酰胺或羧酸)能够与本身可质子化的基团如氨基形成内盐。盐还可以通过碱作用于通式(I)的化合物而形成。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。这些盐为其中酸性氢被农业上合适的阳离子替代的化合物,例如金属盐,特别是碱金属盐或碱土金属盐,特别是钠盐和钾盐,或铵盐,与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。同样有用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。
根据外部条件如pH、溶剂和温度,本发明具有取代的通式(I)的杂芳基氧基吡啶可以多种互变异构的结构存在,所有这些都为通式(I)所涵盖。
根据本发明使用的式(I)的化合物及其盐在下文中称为“通式(I)的化合物”。
本发明优选提供通式(I)的化合物,其中
R1为基团R1-1至R1-42:
R2独立地为卤素、羟基、氨基、氰基、硝基、甲酰基、甲酰胺、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-C4)-卤代烯基、(C2-C4)-卤代炔基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷氧基、(C1-C4)-烯氧基、(C1-C4)-炔氧基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C3-C6)-环烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C3-C6)-环烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C3-C6)-环烷基磺酰基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C3-C6)-环烷基羰基、羧基、(C1-C4)-烷氧基羰基、(C1-C4)-卤代烷氧基羰基、(C3-C6)-环烷氧基羰基、(C1-C4)-烷基氨基羰基、(C2-C6)-二烷基氨基羰基、(C3-C6)-环烷基氨基羰基、(C1-C4)-烷基羰基氨基、(C1-C4)-卤代烷基羰基氨基、(C2-C6)-环烷基羰基氨基、(C1-C4)-烷氧基羰基氨基或(C3-C6)-三烷基甲硅烷基,
n为0、1或2,
R3为卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,
R4为氢、卤素、羟基、氨基、氰基、甲酰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C4)-烷基、(C1-C4)-烷基-(C3-C6)-环烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R4a为氢或(C1-C2)-烷基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、卤素或氰基。
本发明更优选提供通式(I)的化合物,其中
R1为基团R1-1至R1-6,
R2独立地为卤素、羟基、氨基、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷硫基或(C1-C4)-烷基羰基氨基,
n为0、1或2,
R3为卤素、氰基、硝基、(C1-C2)-烷基或(C1-C2)-卤代烷基,
R4为氢、卤素、羟基、氨基、氰基、甲酰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C4)-烷基、(C1-C4)-烷基-(C3-C6)-环烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R4a为氢或(C1-C2)-烷基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、卤素或氰基。
本发明非常特别优选提供通式(I)的化合物,其中
R1为基团R1-1至R1-3,
R2独立地为卤素、氨基、氰基、(C1-C2)-烷基、(C1-C2)-卤代烷基或乙烯基,
n为0、1或2,
R3为卤素、氰基、硝基、(C1-C2)-烷基或(C1-C2)-卤代烷基,
R4为氢、卤素、氰基、甲酰基、(C1-C2)-烷基、(C1-C2)-卤代烷基、(C3-C6)-环烷基、(C1-C2)-烷氧基、(C1-C2)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C2)-烷基、(C1-C2)-烷基-(C3-C6)-环烷基或(C1-C2)-烷氧基-(C1-C2)-烷基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、卤素或氰基。
本发明更优选进一步提供通式(I)的化合物,其中
R1为基团R1-1至R1-3,
R2独立地为氯、溴、氰基或甲基,
n为1或2,
R3为氟、氯、溴、氰基、硝基或三氟甲基,
R4为氢、氯、溴、碘、三氟甲基、二氟甲基、氯氟甲基、二氟氯甲基、二氯甲基、三氯甲基、二氟溴甲基、环丙基、环丙基甲基、(1-甲基)环丙基或甲氧基甲基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、氟、氯或氰基。
本发明最优选提供通式(I)的化合物,其中
R1为基团R1-1、R1-2和R1-3,
R2为甲基,
n为1或2,
R3为氟、氯、溴、氰基或三氟甲基,
R4为氢、溴、碘、环丙基、三氟甲基、二氟甲基、氯氟甲基、二氟氯甲基、环丙基甲基或(1-甲基)环丙基,
X为N或CR5,
Y为N或CH,
以及
R5为氢、氟、氯或氰基。
上述以一般术语列出的或在优选范围内列出的基团的定义既适用于通式(I)的终产物,又相应地适用于每种情况下制备所需的起始材料或中间体。这些基团定义可根据需要彼此组合,即包括给出的优选范围之间的组合。
主要出于更高的除草活性、更好的选择性和/或更好的可制备性的考虑,特别感兴趣的是给出的本发明的通式(I)的化合物或其盐或其本发明的用途,其中各基团具有已指定的或下文指定的优选含义中的一种,或者特别是其中已指定的或下文指定的优选含义中的一种或更多种以组合方式出现的那些。
关于本发明的化合物,将说明上文使用的和下文进一步使用的术语。这些术语是本领域技术人员所熟悉的,并且特别地具有下文中说明的定义:
除非有不同的定义,通常应这样理解化学基团的名称,使得通过最后提及的相关化学基团的结构元素连接到分子的骨架或其余部分,即,例如在(C1-C4)-烷氧基的情况下通过氧原子连接到分子的骨架或其余部分,以及在羧基-(C1-C4)-烷基或(C1-C4)-烷氧基-(C1-C4)-烷基的情况下,在每种情况下通过烷基的碳原子连接到分子的骨架或其余部分。
根据本发明,“烷基磺酰基”——单独或作为化学基团的一部分——代表优选具有1至4个碳原子的直链或支链的烷基磺酰基,例如(但不限于)(C1-C4)-烷基磺酰基,例如甲基磺酰基、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。
根据本发明,“烷硫基”——单独或作为化学基团的一部分——代表优选具有1至4个碳原子的直链或支链的S-烷基,例如(C1-C4)-烷硫基,例如(但不限于)(C1-C4)-烷硫基,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、1,1-二甲基乙硫基。
根据本发明,除非另有不同定义,“烷基亚磺酰基(烷基-S(=O)-)”代表通过-S(=O)-键合至骨架的烷基基团,例如(C1-C4)-烷基亚磺酰基,例如(但不限于)(C1-C4)-烷基亚磺酰基,例如甲基亚磺酰基、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。
“烷氧基”表示通过氧原子连接的烷基基团,例如(但不限于)(C1-C4)-烷氧基,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、1,1-二甲基乙氧基。
根据本发明,除非另有不同定义,“烷基羰基”(烷基-C(=O)-)代表通过-C(=O)-键合至骨架的烷基基团,例如(C1-C4)-烷基羰基。本文中,碳原子数与烷基羰基基团中的烷基基团有关。
除非另有不同定义,“烷氧基羰基(烷基-O-C(=O)-)”:通过-O-C(=O)-键合至骨架的烷基基团,例如(C1-C4)-烷氧基羰基。本文中,碳原子数与烷氧基羰基基团中的烷基基团有关。
除非另有不同定义,“烷氧基硫代羰基(烷基-O-C(=S)-)”:通过-O-C(=S)-键合至骨架的烷基基团,例如(C1-C4)-烷氧基硫代羰基。本文中,碳原子数与烷氧基硫代羰基基团中的烷基基团有关。
术语“卤素”表示例如氟、氯、溴或碘。如果该术语用于基团,则“卤素”表示例如氟、氯、溴或碘原子。
根据本发明,“烷基”表示直链或支链的开链饱和烃基,其任选地被单取代或多取代,并且在后一种情况下称为“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、氟烷基、氰基、硝基、氟、氯、溴或碘。前缀“双(bis)”还包括不同的烷基基团组合,例如甲基(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的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,例如CH2CH2Cl、CH2CH2Br、CHClCH3、CH2Cl、CH2F;二卤代烷基,例如CHF2、CHCl2;全卤代烷基,例如CF3、CCl3、CClF2、CBrF2、CFCl2、CF2CClF2、CF2CClFCF3;多卤代烷基,例如CH2CHFCl、CF2CClFH、CF2CBrFH、CH2CF3;术语全卤代烷基还包括术语全氟烷基。
“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。
例如本文提及的表述“(C1-C4)-烷基”是根据所述碳原子范围对具有1至4个碳原子的直链或支链烷基的简称,即包括甲基、乙基、1-丙基、2-丙基、1-丁基、2-丁基、2-甲基丙基或叔丁基基团。
除非特别说明,在烃基如烷基、烯基和炔基基团,包括复合基团中的烃基的情况下,优选低级碳骨架,例如具有1至6个碳原子,或在不饱和基团的情况下具有2至6个碳原子。烷基基团,包括在复合基团如烷氧基、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;烯基和炔基基团定义为对应于烷基基团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“烯基”还特别包括具有多于一个双键的直链或支链的开链烃基,如1,3-丁二烯基和1,4-戊二烯基,还有具有一个或多个累积双键的丙二烯基或累积多烯基,例如丙二烯基(1,2-丙二烯基)和1,2-丁二烯基。烯基表示,例如可以任选地被其他烷基基团取代的乙烯基,例如(但不限于)(C2-C4)-烯基,例如乙烯基、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。
术语“炔基”还特别包括具有多于一个三键,或具有一个或多个三键和一个或多个双键的直链或支链的开链烃基,例如1,3-丁三烯基。(C2-C4)-炔基表示,例如乙炔基、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。
术语“环烷基”是指具有优选3-6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,其任选地被进一步取代,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、双烷基氨基、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状体系,还包括在环烷基基团上具有双键的取代基,例如亚烷基基团,例如亚甲基。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-基和双环[2.1.1]己基,以及体系如1,1'-双(环丙基)-1-基、1,1'-双(环丙基)-2-基。术语“(C3-C6)-环烷基”是对应于指定碳原子范围的具有3至6个碳原子的环烷基的简称。
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。
根据本发明,“卤代烷硫基”——其本身或作为化学基团的一部分——代表优选具有1至4个碳原子的直链或支链的S-卤代烷基,例如(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-基硫基、2,2,2-二氟乙-1-基硫基、3,3,3-丙-1-基硫基。
“卤代环烷基”表示被相同或不同的卤素原子(例如F、Cl和Br)或被卤代烷基(如三氟甲基或二氟甲基)部分取代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。
根据本发明,“三烷基甲硅烷基”——其本身或作为化学基团的一部分——代表优选具有1至6个碳原子的直链或支链的Si-烷基,例如三[(C1-C2)-烷基]甲硅烷基,例如(但不限于)三甲基甲硅烷基、三乙基甲硅烷基。
如果取代基(例如(C1-C4)-烷基)的集合术语(collective term)位于复合取代基的末端,例如在(C3-C6)-环烷基-(C1-C4)-烷基中,在复合取代基开始的成分(例如(C3-C6)-环烷基)可以被后一取代基(在本实例中为(C1-C4)-烷基)相同或不同且独立地单取代或多取代。
除非有不同的定义,集合术语的定义也适用于复合取代基中的这些集合术语。实例:(C1-C4)-烷基的定义也适用于作为复合取代基——例如,(C3-C6)-环烷基-(C1-C4)-烷基——的组分的(C1-C4)-烷基。
如果化合物可通过氢转移形成其结构在形式上未被通式(I)涵盖的互变异构体,则这些互变异构体仍为本发明的通式(I)的化合物的定义所涵盖,除非考虑特定的互变异构体。例如,许多羰基化合物可以酮形式和以烯醇形式存在,这两种形式都为通式(I)的化合物的定义所涵盖。
根据取代基的性质和其连接的方式,通式(I)的化合物可作为立体异构体存在。通过立体异构体的特定三维形式定义的可能的立体异构体,例如对映异构体、非对映异构体、Z异构体和E异构体均被通式(I)涵盖。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异构体和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。立体异构体可通过常规分离方法从制备中获得的混合物中获得。可进行分析级的色谱分离以发现对映体过量或非对映体过量,或进行制备级的色谱分离以制备用于生物试验的试验样品。同样可通过使用光学活性起始材料和/或助剂通过使用立体选择性反应来选择性地制备立体异构体。因此,本发明还涉及为通式(I)所包括但未以其特定立体异构形式示出的所有立体异构体,及其混合物。
如果化合物作为固体获得,则也可通过重结晶或浸提进行纯化。如果个别的化合物(I)不能通过下述途径以令人满意的方式获得,则它们可通过其他化合物(I)的衍生化来制备。
合适的分离方法、纯化方法和用于分离通式(I)的化合物的立体异构体的方法是本领域技术人员从类似的情况中通常已知的方法,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,剩下的任何混合物通常可通过色谱分离来分离,例如在手性固相上。适于制备量或工业规模的方法是例如结晶的方法,例如非对映体盐的结晶,所述非对映体盐可使用光学活性酸,以及如果合适,使用光学活性碱(条件是存在酸性基团)从非对映异构体混合物中获得。
本发明还要求保护制备本发明的通式(I)的化合物的方法。
本发明的通式(I)的化合物尤其可以使用已知方法制备。所使用和经检查的合成路线从市售可得的或易于制备的结构单元开始进行。在随后的方案中,通式(I)中的部分R1、R2、R3、R4和n具有上文定义的含义,除非给出示例性但非限制性的定义。
本发明的化合物可例如通过方案1中指定的方法制备。
方案1.
通式(I)的杂芳基氧基吡啶可通过羟基吡啶(E-I)在碱的存在下与吡啶、嘧啶或吡嗪(E-II)烷基化制备,其中LG是离去基团。碱可以是碱金属(例如钠、钾或铯)的碳酸盐或碳酸银。反应通常在有机溶剂,例如乙腈、丁腈、二甲基甲酰胺或1-甲基-2-吡咯烷酮中,在0℃至溶剂沸点之间的温度下进行。方案1中提及的R1、R2、R3、X和Y基团以及角标n符合上文给出的定义。
方案2.
通式(E-Ia)的吡啶可通过吡啶(E-III)在氢溴酸和乙酸或三溴化硼的存在下去甲基化制备(方案2)。与三溴化硼的反应通常在有机溶剂,例如二氯甲烷中,在0℃至溶剂沸点之间的温度下进行。
通式(E-III)的吡啶可通过吡啶(E-IV)与吡唑(EV)在催化剂、配体和碱的存在下偶联来制备,其中Hal是卤素如碘或溴。催化剂可以是铜盐(例如CuI)。配体可以是胺(例如N,N'-二甲基乙烷-1,2-二胺或N,N-二甲基甘氨酸)。碱可以是碱金属(例如钠、钾或铯)的碳酸盐。反应通常在有机溶剂,例如1,4-二噁烷、二甲基甲酰胺或二甲基乙酰胺中,在0℃至溶剂沸点之间的温度下进行。
吡啶(E-IV)的合成是本领域技术人员已知的并且记载于例如WO2011/48525和US2013/143907中。方案2中提及的R2和R4基团以及角标n符合上文给出的定义。
方案3.
通式(E-Ic)的吡啶可通过吡啶(E-VIII)在酸性或碱性条件下脱氢制备。酸性条件下的反应在酸(例如盐酸和乙酸)的存在下进行。碱性条件下的反应在碱(例如碱金属碳酸盐)和有机溶剂(例如乙腈或二甲基甲酰胺)的存在下,在0℃至溶剂沸点之间的温度下进行。
通式(E-Ib)和(E-VIII)的吡啶可通过二酮(E-VII)与羟胺或盐酸羟胺的反应制备。反应通常在有机溶剂,例如甲醇或乙醇中,在0℃至溶剂沸点之间的温度下进行。
通式(E-VII)的二酮可通过酮(E-V)与酯(E-VI)在碱的存在下反应制备。碱可以是醇(例如甲醇或乙醇)的钠盐。反应通常在有机溶剂,例如四氢呋喃、甲醇或乙醇中,在0℃至溶剂沸点之间的温度下进行。
酮(E-V)的合成是本领域技术人员已知的并且记载于例如J.Org.Chem.1970,35,3596-3600和Chem.Pharm.Bull.1976,24,303-309中。方案3中提及的R2和R4基团以及角标n符合上文给出的定义。
合成实施例
合成实施例编号I-8:
合成阶段1:(Z)-1,1-二氟-4-羟基-4-(2-羟基-4,6-二甲基-3-吡啶基)丁-3-烯-2-酮(中间体A-01)
将3-乙酰基-4,6-二甲基吡啶-2(1H)-酮(11.40g,69.0mmol)、2,2-二氟乙酸乙酯(10.16ml,96.6mmol)和甲醇钠(30%于甲醇中的溶液,37.3g,207.0mmol)于80ml四氢呋喃中的混合物在60℃下加热4小时。将所得反应混合物冷却至室温,浓缩,用水(25ml)稀释,然后用2M盐酸调至pH 6-7。随后过滤分离得到(Z)-1,1-二氟-4-羟基-4-(2-羟基-4,6-二甲基-3-吡啶基)丁-3-烯-2-酮。产量为7.10g(理论值的42%)。
合成阶段2:4,6-二甲基-3-[3-(二氟甲基)异噁唑-5-基]吡啶-2-醇(中间体A-02)和3-(2-羟基-4,6-二甲基-3-吡啶基)-5-(二氟甲基)-4H-异噁唑-5-醇(中间体A-03)
将(Z)-1,1-二氟-4-羟基-4-(2-羟基-4,6-二甲基-3-吡啶基)丁-3-烯-2-酮(中间体A-01,1.50g,6.17mmol)和盐酸羟胺(860mg,12.3mmol)于10ml乙醇中的混合物在90℃下加热3小时。将所得反应混合物冷却至室温。随后过滤分离得到4,6-二甲基-3-[3-(二氟甲基)异噁唑-5-基]吡啶-2-醇。产量为1.07g(理论值的72%)。
将滤液浓缩。将所得粗产物通过柱色谱法(乙酸乙酯/庚烷梯度)进行最终纯化,分离得到3-(2-羟基-4,6-二甲基-3-吡啶基)-5-(二氟甲基)-4H-异噁唑-5-醇。产量为180mg(理论值的11%)。
合成阶段3:5-[2-(5-氯嘧啶-2-基)氧基-4,6-二甲基-3-吡啶基]-3-(二氟甲基)异噁唑(合成实施例编号I-1)
将4,6-二甲基-3-[3-(二氟甲基)异噁唑-5-基]吡啶-2-醇(中间体A-02,150mg,0.59mmol)、2-溴-5-氯嘧啶(120mg,0.52mmol)和碳酸铯(290mg,0.89mmol)于10ml二甲基乙酰胺中的混合物在微波中在100℃下加热60分钟。将所得反应混合物冷却至室温,用水稀释,随后用二氯甲烷重复萃取。然后将合并的有机相用水洗涤,用硫酸镁干燥,过滤并浓缩。随后将所得粗产物通过柱色谱法(乙酸乙酯/庚烷梯度)纯化分离得到5-[2-(5-氯嘧啶-2-基)氧基-4,6-二甲基-3-吡啶基]-3-(二氟甲基)异噁唑(合成实施例编号I-1)。产量为64mg(理论值的31%)。
合成实施例编号I-15:
合成阶段1:3-[5-(二氟甲基)异噁唑-3-基]-4,6-二甲基吡啶-2-醇(中间体A-04)
将3-(2-羟基-4,6-二甲基-3-吡啶基)-5-(二氟甲基)-4H-异噁唑-5-醇(中间体A-03,800mg,2.79mmol)、乙酸(1.9ml)和浓盐酸(0.7ml)的混合物在80℃下加热24小时。将所得反应混合物冷却至室温并用50ml水稀释。随后过滤分离得到3-[5-(二氟甲基)异噁唑-3-基]-4,6-二甲基吡啶-2-醇。产量为690mg(理论值的98%)。
合成阶段2:5-(二氟甲基)-3-[2-(5-氟嘧啶-2-基)氧基-4,6-二甲基-3-吡啶基]异噁唑(合成实施例编号I-3)
将3-[5-(二氟甲基)异噁唑-3-基]-4,6-二甲基吡啶-2-醇(中间体A-04,690mg,2.73mmol)、2-氯-5-氟嘧啶(435mg,3.28mmol)和碳酸铯(1.78g,5.46mmol)于8ml二甲基甲酰胺中的混合物在80℃下加热5小时。将所得反应混合物冷却至室温,用水稀释,随后用二氯甲烷重复萃取。然后将合并的有机相用水洗涤,用硫酸镁干燥,过滤并浓缩。将所得粗产物通过柱色谱法(乙酸乙酯/庚烷梯度)进行最终纯化,分离得到5-(二氟甲基)-3-[2-(5-氟嘧啶-2-基)氧基-4,6-二甲基-3-吡啶基]异噁唑(合成实施例编号I-3)。产量为67mg(理论值的7%)。
类似于上文引用的和在适当的位置列举的制备实施例,获得下文指定的并示于表1中的通式(I)的化合物。
表1
所选实施例的NMR数据
下文列举了所选的本发明的通式(I)化合物的详细合成实施例。以下部分中描述的化学实施例的1H NMR光谱数据(1H NMR为400MHz,溶剂CDCl3或d6-DMSO,内标:四甲基硅烷δ=0.00ppm)是在Bruker仪器上获得的,并且所列信号的含义如下:br=宽峰;s=单峰,d=二重峰,t=三重峰,dd=双二重峰,ddd=双重双二重峰,m=多重峰,q=四重峰,quint=五重峰,sext=六重峰,sept=七重峰,dq=双四重峰,dt=双三重峰。在非对映异构体混合物的情况下,记载了两种非对映异构体中每一种的显著信号或记载了主要非对映异构体的特征信号。
实施例编号I-1:
1H-NMR(400MHz,CDCl3δ,ppm)8.51(s,2H),7.07(s,1H),6.76(t,J=55Hz,1H),6.74(s,1H),2.49(s,3H),2.48(s,3H).
实施例编号I-2:
1H-NMR(400MHz,CDCl3δ,ppm)8.53(s,2H),7.07(s,1H),6.80(s,1H),2.50(s,3H),2.48(s,3H).
实施例编号I-3:
1H-NMR(400MHz,CDCl3δ,ppm)8.42(s,2H),7.40(s,1H),7.08(s,1H),6.64(t,J=55Hz,1H),2.52(s,3H),2.52(s,3H).
实施例编号I-4:
1H-NMR(400MHz,CDCl3δ,ppm)8.44(s,2H),7.05(s,1H),6.76(s,1H),6.76(t,J=55Hz,1H),2.48(s,3H),2.47(s,3H).
实施例编号I-5:
1H-NMR(400MHz,CDCl3δ,ppm)8.51(s,2H),7.13(d,J=50Hz,1H),7.07(s,1H),6.78(s,1H),2.49(s,3H),2.47(s,3H).
实施例编号I-6:
1H-NMR(400MHz,CDCl3δ,ppm)8.43(s,2H),7.51(s,1H),7.09(s,1H),2.52(s,3H),2.52(s,3H).
实施例编号I-7:
1H-NMR(400MHz,CDCl3δ,ppm)8.50(s,2H),7.51(s,1H),7.11(s,1H),2.54(s,3H),2.53(s,3H).
实施例编号I-8:
1H-NMR(400MHz,CDCl3δ,ppm)8.52(s,2H),7.07(s,1H),6.79(s,1H),2.50(s,3H),2.49(s,3H).
实施例编号I-10:
1H-NMR(400MHz,CDCl3δ,ppm)8.49(s,2H),7.39(s,1H),7.10(s,1H),6.63(t,J=55Hz,1H),2.53(s,3H),2.52(s,3H).
实施例编号I-11:
1H-NMR(400MHz,CDCl3δ,ppm)8.29(s,1H),8.26(s,1H),7.00(s,1H),6.81(t,J=55Hz,1H),6.77(s,1H),2.47(s,3H),2.42(s,3H).
实施例编号I-12:
1H-NMR(400MHz,CDCl3δ,ppm)8.58(s,2H),8.30(d,1H),7.22(d,1H),6.98(s,1H),6.63(t,J=50Hz,1H),2.52(s,3H).
实施例编号I-13:
1H-NMR(400MHz,CDCl3δ,ppm)8.52(s,2H),8.30(d,1H),7.20(d,1H),7.01(s,1H),6.78(t,J=55Hz,1H),2.50(s,3H).
实施例编号I-14:
1H-NMR(400MHz,CDCl3δ,ppm)8.09(d,1H),7.56(dd,1H),6.94(s,1H),6.84(s,1H),6.81(t,J=55Hz,1H),2.48(s,3H),2.37(s,3H).
实施例编号I-41:
1H-NMR(400MHz,CDCl3δ,ppm)8.59(s,2H),7.07(s,1H),6.76(t,J=55Hz,1H),6.74(s,1H),2.49(s,3H),2.47(s,3H).
实施例编号I-43:
1H-NMR(400MHz,CDCl3δ,ppm)8.19(dd,1H),7.70(dd,1H),7.00-6.97(m,2H),6.78(t,J=55Hz,1H),6.72(s,1H),2.46(s,3H),2.44(s,3H).
实施例编号I-45:
1H-NMR(400MHz,CDCl3δ,ppm)8.79(s,2H),7.13(s,1H),6.75(t,J=55Hz,1H),6.71(s,1H),2.52(s,3H),2.49(s,3H).
实施例编号I-46:
1H-NMR(400MHz,CDCl3δ,ppm)8.81(s,2H),7.15(s,1H),6.75(t,J=55Hz,1H),6.69(s,1H),2.53(s,3H),2.48(s,3H).
实施例编号I-178:
1H-NMR(400MHz,CDCl3δ,ppm)8.41(s,2H),7.03(s,1H),6.20(s,1H),2.47(s,3H),2.45(s,3H),1.99-1.95(m,1H),1.04-0.99(m,2H),0.82-0.78(m,2H).
实施例编号I-179:
1H-NMR(400MHz,CDCl3δ,ppm)8.47(s,2H),7.04(s,1H),6.18(s,1H),2.48(s,3H),2.46(s,3H),1.99-1.95(m,1H),1.04-0.99(m,2H),0.82-0.78(m,2H).
实施例编号I-180:
1H-NMR(400MHz,d6-DMSOδ,ppm)8.27(dd,1H),8.21(d,1H),7.17(s,1H),6.53(s,1H),2.32(s,3H),2.31(s,3H),2.07-2.01(m,1H),1.05-1.00(m,2H),0.82-0.78(m,2H).
实施例编号I-200:
1H-NMR(400MHz,CDCl3δ,ppm)8.40(s,2H),7.04(s,1H),6.46(s,1H),2.56(d,2H),2.48(s,3H),2.48(s,3H),1.01-0-93(m,1H),0.56-0.51(m,2H),0.22-0.18(m,2H).
实施例编号I-201:
1H-NMR(400MHz,CDCl3δ,ppm)8.47(s,2H),7.06(s,1H),6.44(s,1H),2.56(d,2H),2.50(s,3H),2.48(s,3H),1.01-0-93(m,1H),0.56-0.51(m,2H),0.21-0.17(m,2H).
实施例编号I-202:
1H-NMR(400MHz,CDCl3δ,ppm)8.04(d,1H),7.52(dd,1H),6.93(s,1H),6.52(s,1H),2.61(d,2H),2.47(s,3H),2.38(s,3H),1.05-1-01(m,1H),0.59-0.54(m,2H),0.26-0.22(m,2H).
实施例编号I-244:
1H-NMR(400MHz,CDCl3δ,ppm)8.35(s,2H),7.62(dd,1H),7.55(dd,1H),7.08(s,1H),6.32(dd,1H),2.52(s,3H),2.19(s,3H).
实施例编号I-245:
1H-NMR(400MHz,CDCl3δ,ppm)8.42(s,2H),7.62(dd,1H),7.54(dd,1H),7.10(s,1H),6.32(dd,1H),2.53(s,3H),2.20(s,3H).
实施例编号I-277:
1H-NMR(400MHz,CDCl3δ,ppm)8.39(s,2H),7.59(s,2H),7.07(s,1H),2.50(s,3H),2.20(s,3H).
实施例编号I-278:
1H-NMR(400MHz,CDCl3δ,ppm)8.46(s,2H),7.59-7.57(m,2H),7.08(s,1H),2.51(s,3H),2.20(s,3H).
实施例编号I-288:
1H-NMR(400MHz,CDCl3δ,ppm)8.11(d,1H),7.80(d,1H),6.97(s,1H),6.81(s,1H),6.79(t,J=55Hz,1H),2.48(s,3H),2.41(s,3H).
实施例编号I-289:
1H-NMR(400MHz,CDCl3δ,ppm)8.30(d,1H),7.78(dd,1H),7.03(s,1H),6.80(s,1H),6.80(t,J=55Hz,1H),2.47(s,3H),2.43(s,3H).
实施例编号I-290:
1H-NMR(400MHz,CDCl3δ,ppm)8.35(d,1H),7.99(d,1H),7.06(s,1H),6.79(t,J=55Hz,1H),6.77(s,1H),2.47(s,3H),2.46(s,3H).
实施例编号I-291:
1H-NMR(400MHz,CDCl3δ,ppm)8.44(d,1H),8.12(d,1H),7.06(s,1H),6.79(t,J=55Hz,1H),6.77(s,1H),2.47(s,3H),2.46(s,3H).
实施例编号I-292:
1H-NMR(400MHz,CDCl3δ,ppm)8.48(dd,1H),7.96(dd,1H),7.11(dd,1H),7.08(s,1H),6.76(t,J=55Hz,1H),6.63(s,1H),2.49(s,3H),2.46(s,3H).
实施例编号I-293:
1H-NMR(400MHz,CDCl3δ,ppm)8.10(d,1H),7.50-7.45(m,1H),7.02(dd,1H),6.95(s,1H),6.78(t,J=55Hz,1H),6.76(s,1H),2.46(s,3H),2.42(s,3H).
实施例编号I-294:
1H-NMR(400MHz,CDCl3δ,ppm)8.38(s,2H),7.63-7.61(m,2H),7.06(s,1H),2.50(s,3H),2.19(s,3H).
实施例编号I-295:
1H-NMR(400MHz,CDCl3δ,ppm)8.46(s,2H),7.63(d,1H),7.59(d,1H),7.08(s,1H),2.51(s,3H),2.20(s,3H).
实施例编号I-296:
1H-NMR(400MHz,CDCl3δ,ppm)8.55(s,2H),7.05(s,1H),6.18(s,1H),2.49(s,3H),2.46(s,3H),1.99-1.95(m,1H),1.04-0.99(m,2H),0.82-0.78(m,2H).
实施例编号I-297:
1H-NMR(400MHz,CDCl3δ,ppm)8.46(s,2H),7.05(s,1H),6.18(s,1H),2.49(s,3H),2.46(s,3H),1.44(s,3H),0.98-0.95(m,2H),0.84-0.81(m,2H).
实施例编号I-298:
1H-NMR(400MHz,CDCl3δ,ppm)8.55(s,2H),7.05(s,1H),6.18(s,1H),2.49(s,3H),2.46(s,3H),1.44(s,3H),0.98-0.95(m,2H),0.85-0.81(m,2H).
实施例编号I-299:
1H-NMR(400MHz,CDCl3δ,ppm)8.41(s,2H),7.03(s,1H),6.20(s,1H),2.47(s,3H),2.46(s,3H),1.45(s,3H),0.99-0.96(m,2H),0.84-0.81(m,2H).
实施例编号I-300:
1H-NMR(400MHz,CDCl3δ,ppm)8.55(s,2H),7.06(s,1H),6.43(s,1H),2.56(d,2H),2.50(s,3H),2.48(s,3H),1.01-0-93(m,1H),0.56-0.51(m,2H),0.21-0.17(m,2H).
实施例编号I-301:
1H-NMR(400MHz,CDCl3δ,ppm)8.05(d,1H),7.53(dd,1H),6.91(s,1H),6.26(s,1H),2.45(s,3H),2.37(s,3H),1.49(s,3H),1.05-1.02(m,2H),0.86-0.83(m,2H).
本发明还提供了一种或多种如上所定义的通式(I)的化合物和/或其盐作为除草剂和/或植物生长调节剂的用途,优选在有用植物作物和/或观赏植物中,通式(I)的化合物和/或其盐优选在所述实施方案之一中被视为是优选或特别优选的,特别是一种或多种在每种情况下如上所定义的式(I-1)至(I-301)的化合物和/或其盐。
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
-一种或多种如上所定义的通式(I)的化合物和/或其盐,其优选在所述实施方案之一中被视为优选的或特别优选的,特别是一种或多种在每种情况下如上文所定义的式(I-1)至(I-301)的化合物和/或其盐,或
-如下文所定义的本发明的组合物,
施用至(有害)植物、(有害)植物的种子、(有害)植物在其中或其上生长的土壤或栽培区域。
本发明还提供一种用于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
-一种或多种如上所定义的通式(I)的化合物和/或其盐,其优选在所述实施方案之一中被视为优选的或特别优选的,特别是一种或多种在每种情况下如上文所定义的式(I-1)至(I-301)的化合物和/或其盐,或
-如下文所定义的本发明的组合物,
施用至不想要的植物(例如有害植物,例如单子叶杂草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,例如谷物、种子或无性繁殖器官如块茎或带芽的嫩枝部分)、不想要的植物在其中或其上生长的土壤(例如作物种植地土壤或非作物种植地土壤)或栽培区域(即不想要的植物将在其上生长的区域)。
本发明还提供一种用于调节植物、优选有用植物的生长的方法,其特征在于将有效量的-一种或多种如上所定义的通式(I)的化合物和/或其盐,其优选在所述实施方案之一中被视为优选的或特别优选的,特别是一种或多种在每种情况下如上文所定义的式(I-1)至(I-301)的化合物和/或其盐,或
-如下文所定义的本发明的组合物,
施用至植物、植物的种子(即植物种子,例如谷物、种子或无性繁殖器官如块茎或带芽的嫩枝部分)、植物在其中或其上生长的土壤(例如耕地土壤或非耕地土壤)或栽培区域(即植物将其上生长的区域)。
在本发明的上下文中,本发明化合物或本发明组合物可通过例如预播种(如果合适,还通过掺入土壤中)、苗前法和/或苗后法施用。可通过本发明化合物防治的单子叶和双子叶杂草植物群的一些代表性的具体实例如下,尽管无意限于所列举的特定物种。
在本发明用于防治有害植物或用于调节植物生长的方法中,优选使用一种或多种通式(I)的化合物和/或其盐来防治有害植物或调节有用植物作物或观赏植物的生长,其中在优选的配置中,所述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/或其盐适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)、阿披拉草属(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)、蟋蟀草属(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)、蔗草属(Scirpus)、狗尾草属(Setaria)、高粱属(Sorghum)。
以下属的双子叶有害植物:苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、蔓锦葵属(Anoda)、春黄菊属(Anthemis)、蔷薇属(Aphanes)、蒿属(Artemisia)、滨藜属(Atriplex)、雏菊属(Bellis)、鬼针草属(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)、猪殃殃属(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)、粟米草属(Mullugo)、勿忘我属(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)、白芥属(Sinapis)、茄属(Solanum)、苦莴菜属(Sonchus)、尖瓣花属(Sphenoclea)、繁缕属(Stellaria)、蒲公英属(Taraxacum)、菥蓂属(Thlaspi)、三叶草属(Trifolium)、荨麻属(Urtica)、婆婆纳属(Veronica)、堇菜属(Viola)、苍耳属(Xanthium)。
当将本发明通式(I)的化合物在有害植物(禾本科杂草和/或阔叶杂草)的出苗前施用于土壤表面(苗前法)时,可完全阻止禾本科杂草或阔叶杂草幼苗的出苗,或其生长直至其到达子叶期,但随后停止生长并最终在三至四周后完全死亡。
如果在出苗后将通式(I)的活性成分施用至植物的绿色部位,则生长在处理后停止,且所述有害植物停留在施用时的生长阶段,或其在一定时间后完全死亡,从而以此方式非常早地并以持久的方式消除对作物植物有害的杂草的竞争。
尽管本发明通式(I)的化合物对单子叶和双子叶杂草显示出优异的除草活性,但是仅轻微损害或完全不损害经济上重要的作物的作物植物,这取决于本发明的化合物的各自结构及其施用率,所述经济上重要的作物植物为例如以下属的双子叶作物:落花生属(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)、棉花属(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、大麦属(Hordeum)、稻属(Oryza)、黍属、甘蔗属(Saccharum)、黑麦属(Secale)、高粱属、黑小麦属(Triticale)、小麦属(Triticum)、玉蜀黍属(Zea)。由于这些原因,本发明化合物非常适于在植物作物(例如农业上有用的植物或观赏植物)中选择性防治不想要的植物的生长。
此外,本发明的通式(I)的化合物(取决于其特定的结构和使用的施用率)在作物植物中具有显著的生长调节性能。它们通过调节作用干预植物自身的新陈代谢,并因此可用于受控地影响植物的成分,并促进采收,例如通过引发脱水和矮化生长。此外,它们还适于一般性防治和抑制不想要的营养生长,而在此过程中不会杀死植物。营养生长的抑制对许多单子叶及双子叶作物起重要作用,因为例如其可减少或完全防止倒伏。
通式(I)的活性成分凭借其除草和植物生长调节性能,也可用于防治基因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,转基因植物的特征为特别有利的性能,例如对某些农药(特别是某些除草剂)的抗性,对植物病害或植物病害的病原体(例如某些昆虫或微生物如真菌、细菌或病毒)的抗性。其他具体的特征涉及例如采收物的产量、品质、贮存性、组成和具体成分。例如,存在已知的淀粉含量增加或淀粉品质改变的转基因植物,或采收物中具有不同脂肪酸组成的那些转基因植物。
就转基因作物而言,优选将本发明的通式(I)的化合物和/或其盐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、黍、稻和玉米,或作物如甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆和其他蔬菜。
优选在对除草剂的植物毒性作用具有抗性或已通过重组方法使其具有抗性的有用植物的作物中,将本发明的通式(I)的化合物用作除草剂。
本发明的通式(I)的化合物凭借其除草和植物生长调节性能,也可在已知的或有待开发的基因修饰植物的作物中,用于防治有害植物。通常,转基因植物的特征在于特别有利的性能,例如对某些农药(特别是某些除草剂)的抗性,对植物病害或植物病害的病原体(例如某些昆虫或微生物如真菌、细菌或病毒)的抗性。其他具体特征涉及例如有关采收物的产量、品质、贮存性、组成和具体成分。例如,存在已知的淀粉含量增加或淀粉品质改变的转基因植物,或采收物中具有不同脂肪酸组成的那些转基因植物。其他特定性能可为对非生物胁迫因素(例如热、冷、干旱、盐和紫外线辐射)的耐受性或抗性。
优选本发明的通式(I)的化合物或其盐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,所述作物例如谷类如小麦、大麦、黑麦、燕麦、黑小麦、黍、稻、木薯和玉米,或作物如甜菜、棉花、大豆、油菜、马铃薯、番茄、豌豆和其他植物。
优选在对除草剂的植物毒性作用具有抗性或已通过重组方法使其具有抗性的有用植物的作物中,将通式(I)的化合物用作除草剂。
制备与现有植物相比具有改进的性能的新植物的常规方法在于例如传统培育方法和产生突变体。或者,具有改变的性能的新植物可借助于重组方法产生。
可用于产生具有改进的性能的新的转基因植物的许多分子生物技术是本领域技术人员已知的。对于这种遗传操作,可将允许通过DNA序列重组进行突变或序列改变的核酸分子引入到质粒中。借助于标准方法,例如可进行碱基交换、移除部分序列或添加天然或合成序列。为将DNA片段彼此连接,可向片段中加入衔接子(adapter)或接头(linker)。
例如,通过表达至少一种相应的反义RNA、用于实现共抑制作用的正义RNA,或通过表达至少一种适当构建的特异性切割上述基因产物的转录物的核酶,可实现产生具有降低的基因产物活性的植物细胞。
为此,首先可使用包含基因产物的整个编码序列(包括可存在的任何侧翼序列)的DNA分子,以及仅包含部分编码序列的DNA分子,在这种情况下这些部分需要足够长以在细胞中具有反义作用。还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。
当在植物中表达核酸分子时,合成的蛋白质可位于植物细胞的任何所需区室中。然而,为实现在特定区室内的定位,例如可将编码区连接到确保定位于特定区室中的DNA序列。这类序列是本领域技术人员已知的(参见,例如Braun等人,EMBO J.11(1992),3219-3227)。核酸分子也可在植物细胞的细胞器中表达。
可通过已知技术再生转基因植物细胞以产生整个植物。原则上,转基因植物可为任何所需植物种类的植物,即不仅有单子叶植物,还有双子叶植物。
以这种方式获得的为具有通过过表达、阻遏(suppression)或抑制(inhibition)同源(=天然)基因或基因序列,或表达异源(=外源)基因或基因序列而改变的特性的转基因植物。
优选将本发明的通式(I)的化合物用于转基因作物中,所述转基因作物对生长调节剂(例如麦草畏(dicamba))具有抗性,或对抑制必需植物酶(例如乙酰乳酸合成酶(ALS)、EPSP合成酶、谷氨酰胺合成酶(GS)或羟基苯丙酮酸双加氧酶(HPPD))的除草剂具有抗性,或对选自磺酰脲类、草甘膦(glyphosate)、草铵膦(glufosinate)或苯甲酰基异噁唑类和类似的活性成分的除草剂具有抗性。
当将本发明的通式(I)的化合物用于转基因作物中时,不仅发生在其他作物中观察到的对有害植物的作用,还常常发生施用于特定转基因作物的特殊的效果,例如改变的或特别拓宽的可防治的杂草谱、可用于施用的改变的施用率、优选与转基因作物对其具有抗性的除草剂的良好的相容性,以及影响转基因作物植物的生长和产量。
因此,本发明还涉及本发明的通式(I)的化合物和/或其盐在有用植物或观赏植物作物、任选地在转基因作物植物中作为除草剂用于防治有害植物的用途。
优选通过苗前法或苗后法,将通式(I)的化合物用于谷类,此处优选玉米、小麦、大麦、黑麦、燕麦、黍或稻。
还优选通过苗前法或苗后法在大豆中使用通式(I)的化合物。
本发明的式(I)的化合物用于防治有害植物或用于植物的生长调节的用途还包括这样的情况,其中通式(I)的化合物或其盐直至在施用到植物上、植物中或土壤中之后才由前体物质(“前药”)形成。
本发明还提供一种或多种通式(I)的化合物或其盐或本发明的组合物(如下文所定义)(在方法中)用于防治有害植物或用于调节植物的生长的用途,其包括将有效量的一种或多种通式(I)的化合物或其盐施用到植物(有害植物,如果合适与有用植物一起)、植物种子、植物在其中或其上生长的土壤或栽培区域上。
本发明还提供一种除草和/或植物生长调节组合物,其特征在于所述组合物包含
(a)一种或多种如上所定义的通式(I)的化合物和/或其盐,其优选在实施方案之一中被视为优选的或特别优选的,特别是一种或多种在每种情况下如上文所定义的式(I-1)至(I-301)的化合物和/或其盐,
和
(b)一种或多种选自组(i)和/或(ii)的其他物质:
(i)一种或多种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(即不符合上文所定义的通式(I)的那些)、杀真菌剂、安全剂、肥料和/或其他生长调节剂,
(ii)一种或多种作物保护中常规的制剂助剂。
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“The PesticideManual”,第16版,The British Crop Protection Council and the Royal Soc.ofChemistry,2012中提及的物质。
本发明的除草组合物或植物生长调节组合物优选包括一种、两种、三种或更多种常用于作物保护中的制剂助剂(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、撒粉剂(dusting agent)、在25℃和1013毫巴下为固体的载体(优选吸附性颗粒状惰性材料)、润湿剂、抗氧化剂、稳定剂、缓冲物质、消沫剂、水、有机溶剂(优选在25℃和1013毫巴下与水以任意比例可混溶的有机溶剂)。
本发明的通式(I)的化合物可以以常规制剂中的可湿性粉剂、可乳化浓缩剂、可喷雾溶液剂、撒粉产品(dusting product)或颗粒剂的形式使用。因此,本发明还提供包含通式(I)的化合物和/或其盐的除草组合物和植物生长调节组合物。
根据指定的生物学和/或物理化学参数,可以以多种方式配制本发明的通式(I)的化合物和/或其盐。可能的制剂包括,例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩剂、可乳化浓缩剂(EC)、乳剂(EW)如水包油乳剂和油包水乳剂、可喷雾溶液剂、悬浮浓缩剂(SC)、基于油或水的分散剂、油混溶性溶液剂、微囊悬浮剂(CS)、撒粉产品(DP)、拌种产品、用于撒播和土壤施用的颗粒剂、微颗粒形式的颗粒剂(GR)、喷雾颗粒剂、吸收和吸附颗粒剂、水分散性颗粒剂(WG)、水溶性颗粒剂(SG)、ULV制剂、微胶囊剂和蜡剂(wax)。
这些单个的制剂类型和制剂助剂(如惰性材料、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,Watkins,"Handbook of Insecticide DustDiluents 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 andEmulsifiers Annual",MC Publ.Corp.,Ridgewood N.J.;Sisley and Wood,"Encyclopedia of Surface Active Agents",Chem.Publ.Co.Inc.,N.Y.1964;[Interface-active Ethylene Oxide Adducts],Wiss.Verlagsgesellschaft,Stuttgart 1976;Winnacker-"Chemische Technologie",第7卷,C.Hanser Verlag Munich,第四版,1986。
可湿性粉剂为可在水中均匀分散的制剂,其除活性成分之外,还包含除稀释剂或惰性物质之外的离子和/或非离子类型的表面活性剂(润湿剂、分散剂),例如聚乙氧基化烷基酚类、聚乙氧基化脂肪醇类、聚乙氧基化脂肪胺类、脂肪醇聚乙二醇醚硫酸盐、烷基磺酸盐、烷基苯磺酸盐、木质素磺酸钠、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。为制备所述可湿性粉剂,在例如常规设备如锤式研磨机、鼓风式研磨机和喷气式研磨机中细磨活性除草成分,并同时或随后与制剂助剂混合。
可乳化浓缩剂通过将活性成分溶于有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯或相对高沸点的芳族化合物或烃类)或有机溶剂的混合物中,并添加一种或多种离子和/或非离子表面活性剂(乳化剂)制备。可使用的乳化剂的实例为:烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙,或非离子乳化剂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、脱水山梨糖醇酯如脱水山梨糖醇脂肪酸酯或聚氧乙烯脱水山梨糖醇酯如聚氧乙烯脱水山梨糖醇脂肪酸酯。
撒粉产品通过将活性成分与细分散的固体一起研磨获得,所述细分散的固体例如滑石、天然粘土(如高岭土、膨润土和叶蜡石)或硅藻土。
悬浮浓缩剂可为水基或油基的。其可借助市售珠磨机并任选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例如湿式研磨法制备。
乳剂,例如水包油乳剂(EW),可使用含水有机溶剂和任选地已在上文例如针对其他制剂型所列的表面活性剂,借助例如搅拌器、胶体磨机和/或静态混合器制备。
颗粒剂可通过将活性成分喷雾到能够吸附的颗粒状惰性材料上制备或借助胶黏剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)将活性成分浓缩物施用于载体物质(例如砂、高岭石或颗粒状惰性材料)的表面上制备。还可将合适的活性成分以常规用于制备肥料颗粒的方式——如果需要与肥料相混合——成粒。
水分散性颗粒剂通常通过常规方法如喷雾干燥法、流化床造粒法、盘式造粒法、用高速混合器混合以及在无固体惰性材料的情况下挤出而制备。
对于盘式颗粒、流化床颗粒、挤出颗粒和喷雾颗粒的制备,参见例如在“SprayDrying Handbook”第三版,1979,G.Goodwin Ltd.,London;J.E.Browning,“Agglomeration”,Chemical and Engineering 1967,第147页及后文;“Perry's ChemicalEngineer's Handbook”,第五版,McGraw-Hill,New York 1973,第8-57页中的方法。
有关作物保护组合物制剂的其他详细信息,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。
本发明的农用化学制剂、优选除草组合物或植物生长调节组合物,优选包含总量为0.1至99重量%、优选0.5至95重量%、更优选1至90重量%、尤其优选2至80重量%的通式(I)的活性成分及其盐。
在可湿性粉剂中,活性成分的浓度为例如约10重量%至90重量%,补足至100重量%的余量由常规制剂成分组成。在可乳化浓缩剂中,活性成分的浓度可为约1重量%至90重量%且优选5重量%至80重量%。粉剂形式的制剂包含1重量%至30重量%的活性成分、优选地通常5重量%至20重量%的活性成分;可喷雾溶液剂包含约0.05重量%至80重量%、优选2重量%至50重量%的活性成分。在水分散性颗粒剂的情况下,活性成分含量部分取决于活性化合物是液体形式还是固体形式,以及所使用的造粒助剂、填充剂等。在水分散性颗粒剂中,活性成分的含量例如为1重量%至95重量%、优选10重量%至80重量%。
此外,所提及的活性成分制剂任选地包含各种常规的粘着剂、润湿剂、分散剂、乳化剂、渗透剂、防腐剂、防冻剂和溶剂、填料、载体和染料、消泡剂、蒸发抑制剂和影响pH和粘度的试剂。制剂助剂的实例尤其记载于“Chemistry and Technology of AgrochemicalFormulations”,编辑D.A.Knowles,Kluwer Academic Publishers(1998)中。
本发明的通式(I)的化合物或其盐可以其自身或以其与其他农药活性物质(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(配方)形式使用,例如以成品制剂或桶混物(tank mix)的形式。所述组合制剂可在上述制剂的基础上制备,同时考虑要结合的活性成分的物理性质和稳定性。
可用于以混合制剂形式或以桶混物形式的本发明的通式(I)的化合物的组合配伍物质为,例如基于抑制以下物质的已知活性成分:例如乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮莽草酸-3-磷酸合成酶(enolpyruvylshikimate-3-phosphatesynthase)、谷氨酰胺合成酶、对羟基苯丙酮酸双加氧酶、八氢番茄红素脱氢酶(phytoenedesaturase)、光合系统I(photosystem I)、光合系统II、原卟啉原氧化酶(protoporphyrinogen oxidase),如在例如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。
特别感兴趣的是选择性防治有用植物作物和观赏植物中的有害植物。尽管本发明的通式(I)的化合物已经在大量的作物中表现出非常好的至足够的选择性,但原则上,在一些作物中以及特别是在与其他选择性较差的除草剂的混合物的情况下,可能发生对作物植物的植物毒性。在这点上,特别感兴趣的本发明的化合物(I)的组合是包含通式(I)的化合物或其与其他除草剂或农药和安全剂的组合的那些。以解毒有效量使用的安全剂降低施用的除草剂/农药在例如以下作物中的植物毒性副作用:经济上重要的作物,例如谷类(小麦、大麦、黑麦、玉米、稻、黍)、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的施用率和所述安全剂的功效,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。类似于通式(I)的化合物或其混合物,安全剂可与其他除草剂/农药一起配制,并可作为含除草剂的成品制剂或桶混物提供和使用。
为进行施用,如果合适,以常规方式稀释市售形式的除草剂制剂或除草剂-安全剂制剂,例如在可湿性粉剂、可乳化浓缩剂、分散剂和水分散性颗粒剂的情况下,用水稀释。粉剂型制剂、用于土壤施用的颗粒剂或撒播用颗粒剂和可喷雾溶液剂通常在施用前不用其他惰性物质进一步稀释。
通式(I)的化合物和/或其盐的施用率在一定程度上受外部条件如温度、湿度等的影响。施用率可在宽范围内变化。对于作为用于防治有害植物的除草剂的施用,通式(I)的化合物及其盐的总量的优选范围为0.001至10.0kg/ha、优选0.005至5kg/ha、更优选0.01至1.5kg/ha、特别优选0.05至1kg/ha。这既适用于苗前施用,也适用于苗后施用。
当将本发明的通式(I)的化合物和/或其盐用作植物生长调节剂,例如用作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、黍、稻或玉米)的茎秆稳定剂时,总施用率的优选范围为0.001至2kg/ha,优选0.005至1kg/ha,特别是10至500g/ha,非常特别优选20至250g/ha。这既适用于苗前施用,也适用于苗后施用。
作为茎秆稳定剂的施用可在植物生长的各个阶段进行。优选在例如分蘖期之后、纵向生长开始时施用。
或者,作为植物生长调节剂的施用也可通过处理种子(其包括用于拌种和包衣种子的各种技术)进行。施用率取决于特定的技术,并可在初步试验中确定。
本发明的组合物(例如以混合制剂形式或以桶混物形式)中可用于本发明的通式(I)的化合物的组合配伍物质为例如基于抑制以下物质的已知活性成分:例如乙酰乳酸合成酶、乙酰辅酶A羧化酶、纤维素合成酶、烯醇式丙酮莽草酸-3-磷酸合成酶、谷氨酰胺合成酶、对羟基苯丙酮酸双加氧酶、八氢番茄红素脱氢酶、光合系统I、光合系统II或原卟啉原氧化酶,如在例如Weed Research 26(1986)441-445或“The Pesticide Manual”,第16版,TheBritish Crop Protection Council and the Royal Soc.of Chemistry,2012以及其中引用的文献中所记载的。可与本发明化合物结合的已知除草剂或植物生长调节剂为,例如以下活性成分,其中所述活性成分指的是其根据国际标准化组织(ISO)的“通用名称”或化学名称或代码编号。它们总是包括所有的使用形式,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,即使未明确提及它们。
这种除草混合配伍物质的实例为:
乙草胺(acetochlor)、三氟羧草醚(acifluorfen、acifluorfen-sodium)、苯草醚(aclonifen)、甲草胺(alachlor)、二丙烯草胺(allidochlor)、禾草灭(alloxydim)、枯杀达(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(aminocyclopyrachlor-potassium)、环丙嘧啶酸甲酯(aminocyclopyrachlor-methyl)、氯氨吡啶酸(aminopyralid)、杀草强(amitrole)、氨基磺酸铵(ammoniumsulfamate)、莎稗磷(anilofos)、磺草灵(asulam)、莠去津(atrazine)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、草除灵(benazolin、benazolin-ethyl)、乙丁氟灵(benfluralin)、呋草黄(benfuresate)、苄嘧磺隆(bensulfuron、bensulfuron-methyl)、地散磷(bensulide)、灭草松(bentazone)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyron)、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠盐(bilanafos-sodium)、双草醚(bispyribac)、双草醚钠盐bispyribac-sodium)、除草定(bromacil)、溴丁酰草胺(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、丁酰溴苯腈(bromoxynil-butyrate)、溴苯腈钾(bromoxynil-potassium)、庚酰溴苯腈(bromoxynil-heptanoate)和辛酰溴苯腈(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)、丁苯草酮(butroxydim)、丁草敌(butylate)、唑草胺(cafenstrole)、双酰草胺(carbetamide)、唑酮草酯(carfentrazone、carfentrazone-ethyl)、草灭畏(chloramben)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、双氯酚酸钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、氯甲丹(chlorflurenol、chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron、chlorimuron-ethyl)、氯酞酰亚胺(chlorophthalim)、绿麦隆(chlorotoluron)、氯酞酸二甲酯(chlorthal-dimethyl)、氯磺隆(chlorsulfuron)、吲哚酮草酯(cinidon、cinidon-ethyl)、环庚草醚(cinmethylin)、醚磺隆(cinosulfuron)、氯酰草膦(clacyfos)、烯草酮(clethodim)、炔草酸(clodinafop)、炔草酯(clodinafop-propargyl)、异噁草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、氯酯磺草胺(cloransulam、cloransulam-methyl)、苄草隆(cumyluron)、氨基氰(cyanamide)、氰草津(cyanazine)、环草敌(cycloate)、cyclopyrimorate、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop、cyhalofop-butyl)、环草津(cyprazine)、2,4-D、2,4-D-丁氧基乙酯(2,4-D-butotyl)、2,4-D-丁酯(2,4-D-butyl)、2,4-D-二甲基铵(2,4-D-dimethylammonium)、2,4-D-二乙醇胺(2,4-D-diolamin)、2,4-D-乙酯(2,4-D-ethyl)、2,4-D-2-乙基己酯(2-ethylhexyl)、2,4-D-异丁酯、2,4-D-异辛酯、2,4-D-异丙基铵、2,4-D-钾、2,4-D-三异丙醇铵和2,4-D-三乙醇胺、2,4-DB、2,4-DB-丁酯、2,4-DB-二甲基铵、2,4-DB-异辛酯、2,4-DB-钾和2,4-DB-钠、杀草隆(daimuron(dymron))、茅草枯(dalapon)、棉隆(dazomet)、正癸醇、甜菜安(desmedipham)、detosyl-pyrazolate(DTP)、麦草畏、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)、精2,4-滴丙酸(dichlorprop-P)、禾草灵(diclofop、diclofop-methyl)、diclofop-P-methyl、双氯磺草胺(diclosulam)、野燕枯(difenzoquat)、吡氟酰草胺(diflufenican)、二氟吡隆(diflufenzopyr)、氟吡草腙(diflufenzopyr-sodium)、噁唑隆(dimefuron)、哌草丹(dimepiperate)、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)、双苯酰草胺(diphenamid)、敌草快(diquat、diquat-dibromid)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron、ethametsulfuron-methyl)、乙嗪草酮(ethiozin)、乙氧呋草黄(ethofumesate)、氟乳醚(ethoxyfen)、氯氟草醚乙酯(ethoxyfen-ethyl)、乙氧嘧磺隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、F-9600、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)、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、精噁唑禾草灵(fenoxaprop-P-ethyl)、fenoxasulfone、fenquinotrione、四唑酰草胺(fentrazamide)、麦草伏(flamprop)、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)、吡氟禾草灵(fluazifop)、精吡氟禾草灵(fluazifop-P)、吡氟禾草灵丁酯(fluazifop-butyl)、精吡氟禾草灵丁酯(fluazifop-P-butyl)、氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、氟哒嗪草酯(flufenpyr、flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac、flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、flurenol-dimethylammonium和芴醇甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen、fluoroglycofen-ethyl)、四氟丙酸(flupropanate)、氟啶嘧磺隆(flupyrsulfuron、flupyrsulfuron-methyl-sodium)、氟啶草酮(fluridone)、氟咯草酮(flurochloridone)、氯氟吡氧乙酸(fluroxypyr、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(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、杀木膦(fosamine)、草铵膦、草铵膦铵、精草铵膦钠(glufosinate-P-sodium)、精草铵膦铵、精草铵膦钠、草甘膦、草甘膦铵、草甘膦异丙基铵、草甘膦二铵、草甘膦二甲基铵、草甘膦钾、草甘膦钠和草硫膦(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-ethyl isopropylphosphoramidothioate))、氟氯吡啶酯(halauxifen、halauxifen-methyl)、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron、halosulfuron-methyl)、氟吡禾灵(haloxyfop)、精氟吡禾灵(haloxyfop-P)、氟吡禾灵乙氧基乙酯、精氟吡禾灵乙氧基乙酯、氟吡甲禾灵(haloxyfop-methyl)、高效氟吡甲禾灵(haloxyfop-P-methyl)、环嗪酮(hexazinone)、HW-02(即1-(二甲氧基磷酰基)乙基(2,4-二氯苯氧基)乙酸酯)、咪草酯(imazamethabenz、imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟铵、甲咪唑烟酸(imazapic)、甲咪唑烟酸铵、咪唑烟酸(imazapyr)、咪唑烟酸异丙铵、咪唑喹啉酸(imazaquin)、咪唑喹啉酸铵、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸亚铵(imazethapyr-immonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、碘甲磺隆(iodosulfuron、iodosulfuron-methyl-sodium)、碘苯腈(ioxynil)、辛酰碘苯腈(ioxynil-octanoate)、碘苯腈钾和碘苯腈钠、三唑酰草胺(ipfencarbazone)、异丙隆(isoproturon)、异噁隆(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、乳氟禾草灵(lactofen)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙酯、MCPA-二甲基铵、MCPA-2-乙基己酯、MCPA-异丙基铵、MCPA-钾和MCPA-钠、MCPB、MCPB-甲酯、MCPB-乙酯和MCPB-钠、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸钠和2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸(mecoprop-P)、精2-甲-4-氯丙酸丁氧基乙酯、精2-甲-4-氯丙酸二甲基铵、精2-甲-4-氯丙酸-2-乙基己酯和精2-甲-4-氯丙酸钾、苯噻酰草胺(mefenacet)、氟磺酰草胺(mefluidide)、甲基二磺隆(mesosulfuron、mesosulfuron-methyl)、甲基磺草酮(mesotrione)、甲基苯噻隆(methabenzthiazuron)、威百亩(metam)、噁唑酰草胺(metamifop)、苯嗪草酮(metamitron)、吡唑草胺(metazachlor)、嗪吡嘧磺隆(metazosulfuron)、甲基苯噻隆、甲硫嘧磺隆(methiopyrsulfuron)、methiozolin、异硫氰酸甲酯(methyl isothiocyanate)、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)、甲磺隆(metsulfuron、metsulfuron-methyl)、禾草敌(molinat)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)、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)、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)、噁嗪草酮(oxaziclomefon)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat、paraquat dichloride)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚(pentachlorophenol)、环戊噁草酮(pentoxazone)、烯草胺(pethoxamid)、矿油(petroleumoils)、甜菜宁(phenmedipham)、氨氯吡啶酸(picloram)、氟吡酰草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、丙草胺(pretilachlor)、氟嘧磺隆(primisulfuron、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)、噁草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠(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)、吡草醚(pyraflufen、pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotole)、吡唑特(pyrazolynate(pyrazolate))、吡嘧磺隆(pyrazosulfuron、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)、达草止(pyridafol)、哒草特(pyridate)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac、pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、嘧草硫醚钠(pyrithiobac-sodium)、砜吡草唑(pyroxasulfone)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、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)、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(sulcotrion)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron、sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-523、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(三氟乙酸)、TCA-钠、丁噻隆(tebuthiuron)、呋喃磺草酮(tefuryltrione)、环磺酮(tembotrione)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、特丁通(terbumeton)、特丁津(terbuthylazin)、特丁净(terbutryn)、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、噻酮磺隆(thiencarbazone、thiencarbazone-methyl)、噻吩磺隆(thifensulfuron、thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralate、苯吡唑草酮(topramezone)、三甲苯草酮(tralkoxydim)、triafamone、野麦畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron、tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、草达津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟啶磺隆钠(trifloxysulfuron-sodium)、trifludimoxazin、氟乐灵(trifluralin)、氟胺磺隆(triflusulfuron、triflusulfuron-methyl)、三氟甲磺隆(tritosulfuron)、硫酸脲、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),以及以下化合物:
可作为混合配伍物质的植物生长调节剂的实例为:
苯并噻二唑(acibenzolar)、苯并噻二唑(acibenzolar-S-methyl)、氨基酮戊酸(5-aminolevulinic acid)、、环丙嘧啶醇(ancymidol)、6-苄基氨基嘌呤、芸苔素内酯(brassinolide)、邻苯二酚(catechol)、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酸酰胺(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆(dazomet)、正癸醇、敌草克(dikegulac)、敌草克钠(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)、芴丁酯(fiurenol-butyl)、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)、茉莉酸甲酯、马来酰肼、助壮素(mepiquat chloride)、1-甲基环丙烯、2-(1-萘基)乙酰胺、1-萘乙酸、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(paclobutrazole)、N-苯基邻苯二甲酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、独角金内酯(strigolactone)、四氧硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac、trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、精烯效唑(uniconazole-P)。
用于本发明的通式(I)的化合物的有用的组合配伍物质还包括,例如以下安全剂:
S1)选自杂环羧酸衍生物的化合物:
S1a)二氯苯基吡唑啉-3-羧酸型的化合物(S1a),优选化合物如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)”),以及如在WO-A-91/07874中记载的相关化合物;
S1b)二氯苯基吡唑羧酸的衍生物(S1b),优选化合物如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),以及如在EP-A-333131和EP-A-269806中记载的相关化合物;
S1c)1,5-二苯基吡唑-3-羧酸的衍生物(S1c),优选化合物如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),以及如在例如EP-A-268554中记载的相关化合物;
S1d)三唑羧酸型的化合物(S1d),优选化合物如解草唑(fenchlorazole)(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),以及如在EP-A-174562和EP-A-346620中记载的相关化合物;
S1e)5-苄基-2-异噁唑啉-3-羧酸或5-苯基-2-异噁唑啉-3-羧酸或5,5-二苯基-2-异噁唑啉-3-羧酸型的化合物(S1e),优选化合物如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),以及如在WO-A-91/08202中记载的相关化合物,或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中所记载的。
S2)选自8-喹啉氧基衍生物的化合物(S2):
S2a)8-喹啉氧基乙酸型的化合物(S2a),优选(5-氯-8-喹啉氧基)乙酸1-甲基己酯(“解草酯(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),以及如EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0 492 366中记载的相关化合物,以及(5-氯-8-喹啉氧基)乙酸(S2-10)、其水合物和盐,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)丙二酸型的化合物(S2b),优选化合物如(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)丙二酸甲基乙基酯,以及如EP-A-0 582 198中记载的相关化合物。
S3)二氯乙酰胺型的活性成分(S3),其通常用作苗前安全剂(作用于土壤的安全剂),例如
“烯丙酰草胺(dichlormid)”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1)、
Stauffer的“R-29148”(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2)、
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)、
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)、
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)、
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)、
TRI-Chemical RT的“TI-35”(1-二氯乙酰基氮杂环庚烷)(S3-8)、
BASF的“diclonon”(dicyclonon)或“BAS145138”或“LAB145138”(S3-9)((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)、
“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),及其(R)异构体(S3-11)。
S4)选自酰基磺酰胺类的化合物(S4):
S4a)式(S4a)的N-酰基磺酰胺及其盐,如WO-A-97/45016中所记载的,
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,并且在环状基团的情况下,还被(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)苯甲酰胺型的化合物及其盐,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,以及
mB为1或2,
例如那些化合物,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)选自式(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,和
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型的化合物及其盐,其从例如CN101838227中已知,
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、(C5-C6)-环烯基。
S5)选自羟基芳族化合物类和芳族-脂族羧酸衍生物类的活性成分(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)选自1,2-二氢喹喔啉-2-酮类的活性成分(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)选自二苯基甲氧基乙酸衍生物类的化合物(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)的化合物或其盐,如WO-A-98/27049中所记载,
其中符号和角标定义如下:
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,其中前述各含碳基团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)选自3-(5-四唑基羰基)-2-喹诺酮类的活性成分(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-1999/000020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)氧基亚氨基化合物型的活性成分(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),其已知为黍/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),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂,和
“解草胺腈(cyometrinil)”或“CGA-43089”((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知为黍/高粱抵抗异丙甲草胺损害的拌种安全剂。
S12)选自异硫代苯并二氢吡喃-4-酮类(isothiochromanones)的活性成分(S12),例如[(3-氧代-1H-2-苯并噻喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登记号205121-04-6)(S12-1)以及来自WO-A-1998/13361的相关化合物。
S13)选自组(S13)的一种或多种化合物:
“萘二甲酸酐”(1,8-萘二甲酸酐)(S13-1),其已知作为拌种安全剂在玉米中用于抵抗硫代氨基甲酸酯除草剂的损害,
“解草啶(fenclorim)”(4,6-二氯-2-苯基嘧啶)(S13-2),其已知作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),其已知作为拌种安全剂在黍/高粱中用于抵抗甲草胺和异丙甲草胺的损害,
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),其已知作为安全剂在玉米中用于抵抗咪唑啉酮的损害,
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),其已知在玉米中用作安全剂,
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-丙烯酯)(S13-6),
“乙拌磷(disulfoton)”(O,O-二乙基S-2-乙硫基乙基二硫代磷酸酯)(S13-7),
“增效磷(dietholate)”(O,O-二乙基O-苯基硫代磷酸酯)(S13-8),“mephenate”(甲基氨基甲酸4-氯苯基酯)(S13-9)。
S14)除对有害植物具有除草作用外,还对作物植物如稻具有安全剂作用的活性成分,例如
“哌草丹(dimepiperate)”或“MY-93”(1-苯基乙基哌啶-1-硫代甲酸S-1-甲酯),其已知作为安全剂在稻中用于抵抗除草剂禾草敌的损害,
“杀草隆(daimuron)”或“SK 23”(1-(1-甲基-1-苯基乙基)-3-对甲苯基脲),其已知作为安全剂在稻中用于抵抗除草剂唑吡嘧磺隆的损害,
“苄草隆(cumyluron)”=“JC-940”(3-(2-氯苯基甲基)-1-(1-甲基-1-苯乙基)脲,参见JP-A-60087270),其已知作为安全剂在稻中用于抵抗一些除草剂的损害,
“苯草酮(methoxyphenone)”或“NK 049”(3,3'-二甲基-4-甲氧基二苯甲酮),其已知作为安全剂在稻中用于抵抗一些除草剂的损害,
Kumiai的“CSB”(1-溴-4-(氯甲基磺酰基)苯)(CAS登记号54091-06-4),其已知作为安全剂在稻中用于抵抗一些除草剂的损害。
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,
其中
RH 1为(C1-C6)-卤代烷基基团,和
RH 2为氢或卤素,和
RH 3、RH 4独立地为氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中最后3个基团各自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、未取代的或取代的(C3-C6)-环烷基、未取代的或取代的苯基和未取代的或取代的杂环基,
或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧稠合至4元至6元饱和或不饱和碳环的(C3-C6)-环烷基,或在环的一侧稠合至4元至6元饱和或不饱和碳环的(C4-C6)-环烯基,
其中最后4个基团各自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、未取代的或取代的(C3-C6)环烷基、未取代的或取代的苯基和未取代的或取代的杂环基,
或
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,和
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为四元至八元杂环,所述杂环除氮原子外,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)主要用作除草剂但也对作物植物具有安全剂作用的活性成分,
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(lactidichloro-ethyl)。
与本发明的通式(I)的化合物和/或其盐、特别是与式(I-1)至(I-301)的化合物和/或其盐结合的优选的安全剂为:解草酯、环丙磺酰胺、解草唑乙酯、双苯噁唑酸、吡唑解草酯、解草啶、苄草隆、S4-1和S4-5,并且特别优选的安全剂为:解草酯、环丙磺酰胺、双苯噁唑酸和吡唑解草酯。
生物学实施例
A.在320g/ha下的出苗后除草功效
将单子叶和双子叶杂草植物的种子置于塑料盆的砂壤土中(播种两次,每种情况下每盆有一种单子叶或双子叶杂草植物),用土壤覆盖并在受控生长条件下在温室中栽培。在播种后2至3周,在一叶期对试验植物进行处理。将本发明的化合物(其以可湿性粉剂(WP)或乳液浓缩剂(EC)形式配制)在添加0.5%的添加剂的情况下以水性悬浮液或乳液的形式在每公顷600升的水施用率(经换算)下施用至植物的绿色部分。在试验植物已在最佳生长条件下在温室中保持约3周后,与未处理的对照组相比,目测评估所述制剂的活性。
例如,100%活性=植物已经死亡,0%活性=如对照植物。
下表A1至A11示出,在相当于320g/ha的施用率下,所选择的根据表1的通式(I)的化合物对多种有害植物的效果,这是通过上述实验方法获得的。
表A1:对苘麻(Abutilon theophrasti)(ABUTH)的出苗后功效
表A2:对大穗看麦娘(Alopecurus myosuroides)(ALOMY)的出苗后功效
表A3:对反枝苋(Amaranthus retroflexus)(AMARE)的出苗后功效
表A4:对马唐(Digitaria sanguinalis)(DIGSA)的出苗后功效
表A5:对稗草(Echinochloa crus-galli)(ECHCG)的出苗后功效
表A6:对细枝雾冰藜(Bassia scoparia)(KCHSC)的出苗后功效
表A7:对早熟禾(Poa annua)(POAAN)的出苗后功效
表A8:对繁缕(Stellaria media)(STEME)的出苗后作用
表A9:对阿拉伯婆婆纳(Veronica persica)(VERPE)的出苗后功效
表A10:对硬直黑麦草(Lolium rigidum)(LOLRI)的出苗后功效
表A11:对狗尾草(Setaria viridis)(SETVI)的出苗后功效
如表A1-A11中的结果举例所示,在出苗后处理的情况下,本发明的化合物编号I-1、I-2、I-3、I-5、I-6、I-7、I-8、I-10、I-11、I-13、I-14、I-41、I-43、I-45、I-46、I-178、I-179、I-180、I-200、I-201、I-202、I-277、I-278、I-288、I-289、I-290、I-291、I-292、I-294、I-295、I-296、I-297、I-298、I-299、I-300和I-301在每公顷320g活性物质的施用率下,对以下有害植物具有非常好的除草功效:苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、马唐(DIGSA)、稗草(ECHCG)、细枝雾冰藜(KCHSC)、硬直黑麦草(LOLRI)、早熟禾(POAAN)、狗尾草(SETVI)、繁缕(STEME)和阿拉伯婆婆纳(VERPE)。
B.在80g/ha下的出苗后除草功效
将单子叶和双子叶杂草植物和作物植物的种子置于塑料或有机种植盆中的砂壤土中,用土壤覆盖并在受控生长条件下在温室中栽培。在播种后2至3周,在一叶期对试验植物进行处理。然后将本发明的化合物(其以可湿性粉剂(WP)形式或以乳液浓缩剂(EC)形式配制)在添加0.5%的添加剂的情况下以水性悬浮液或乳液的形式在600l/ha的水施用率(经换算)下喷洒至植物的绿色部分。在试验植物已在最佳生长条件下在温室中保持约3周后,与未处理的对照组相比,目测评估所述制剂的活性。例如,100%活性=植物已经死亡,0%活性=如对照植物。
下表B1至B6示出,在相当于80g/ha的施用率下,所选择的根据表1的通式(I)的化合物对多种有害植物的效果,这是通过上述实验方法获得的。
表B1:对大穗看麦娘(ALOMY)的出苗后功效
表B2:对反枝苋(AMARE)的出苗后功效
表B3:对卷茎蓼(Polygonum convolvulus)(POLCO)的出苗后功效
表B4:对狗尾草(SETVI)的出苗后功效
表B5:对阿拉伯婆婆纳(VERPE)的出苗后功效
表B6:对三色堇(Viola tricolor)(VIOTR)的出苗后功效
如表B1-B6中的结果举例所示,在出苗后处理的情况下,本发明的化合物编号I-1、I-2、I-3、I-4、I-5、I-7、I-8、I-10、I-14、I-41、I-43、I-45、I-277、I-292、I-293和I-294在每公顷80g活性物质的施用率下,对以下有害植物具有非常好的除草功效:大穗看麦娘(ALOMY)、反枝苋(AMARE)、卷茎蓼(POLCO)、狗尾草(SETVI)、阿拉伯婆婆纳(VERPE)和三色堇(VIOTR)。
C.在320g/ha下的出苗前除草功效
将单子叶和双子叶杂草植物的种子置于塑料盆的砂壤土中(播种两次,在每种情况下每盆有一种单子叶或双子叶杂草植物),用土壤覆盖。然后将本发明的化合物(其以可湿性粉剂(WP)或乳液浓缩剂(EC)形式配制)在添加0.5%的添加剂的情况下作为水性悬浮液或乳液在每公顷600升的水施用率(经换算)下施用至所覆盖土壤的表面。处理后,将盆置于温室中并保持在试验植物的良好的生长条件下。约3周之后,与未处理的对照组相比,目测评估所述制剂以百分比计的效果。
例如,100%活性=植物已经死亡,0%活性=如对照植物。
下表C1至C12示出,在相当于320g/ha的施用率下,所选择的根据表1的通式(I)的化合物对多种有害植物的效果,这是通过上述实验方法获得的。
表C1:对苘麻(ABUTH)的出苗前功效
表C2:对大穗看麦娘(ALOMY)的出苗前功效
表C3:对反枝苋(AMARE)的出苗前功效
表C4:对马唐(DIGSA)的出苗前功效
表C5:对稗草(ECHCG)的出苗前功效
表C6:对细枝雾冰藜(KCHSC)的出苗前功效
表C7:对硬直黑麦草(LOLRI)的出苗前功效
表C8:对无香母菊(Matricaria inodora)(MATIN)的出苗前功效
表C9:对早熟禾(POAAN)的出苗前功效
表C10:对狗尾草(SETVI)的出苗前功效
表C11:对繁缕(STEME)的出苗前功效
表C12:对阿拉伯婆婆纳(VERPE)的出苗前功效
如表C1-C12中的结果举例所示,在出苗前处理的情况下,本发明的化合物编号I-1、I-2、I-3、I-5、I-6、I-7、I-8、I-10、I-11、I-12、I-14、I-41、I-43、I-45、I-46、I-178、I-179、I-180、I-200、I-201、I-202、I-245、I-277、I-278、I-288、I-289、I-291、I-292、I-294、I-295、I-296、I-297、I-298、I-299和I-300在每公顷320g活性物质的施用率下,对以下有害植物具有非常好的除草功效:苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、马唐(DIGSA)、稗草(ECHCG)、细枝雾冰藜(KCHSC)、硬直黑麦草(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)。
D.在80g/ha下的出苗前除草功效
将单子叶和双子叶杂草植物和作物植物的种子置于塑料或有机种植盆中并用土壤覆盖。然后将本发明的化合物(其以可湿性粉剂(WP)形式或以乳液浓缩剂(EC)形式配制)在添加0.5%的添加剂的情况下以水性悬浮液或乳液的形式在600l/ha的水施用率(经换算)下施用至所覆盖土壤的表面。处理后,将盆置于温室中并保持在试验植物的良好的生长条件下。约3周之后,与未处理的对照组相比,目测评估所述制剂以百分比计的效果。例如,100%活性=植物已经死亡,0%活性=如对照植物。
下表D1至D12示出,在相当于80g/ha的施用率下,所选择的根据表1的通式(I)的化合物对多种有害植物的效果,这是通过上述实验方法获得的。
表D1:对苘麻(ABUTH)的出苗前功效
表D2:对大穗看麦娘(ALOMY)的出苗前功效
表D3:对反枝苋(AMARE)的出苗前功效
表D4:对野燕麦(Avena fatua)(AVEFA)的出苗前功效
表D5:对马唐(DIGSA)的出苗前功效
表D6:对无香母菊(MATIN)的出苗前功效
表D7:对圆叶牵牛(Ipomoea purpurea)(PHBPU)的出苗前功效
表D8:对卷茎蓼(POLCO)的出苗前功效
表D9:对狗尾草(SETVI)的出苗前功效
表D10:对阿拉伯婆婆纳(VERPE)的出苗前功效
表D11:对三色堇(VIOTR)的出苗前功效
表D12:对稗草(ECHCG)的出苗前功效
如表D1-D12中的结果举例所示,在出苗前处理的情况下,本发明的化合物编号I-1、I-2、I-3、I-4、I-5、I-7、I-8、I-10、I-14、I-41、I-43、I-45、I-277、I-292、I-293、和I-294在每公顷80g活性物质的施用率下,对以下有害植物具有非常好的除草功效:苘麻(ABUTH)、大穗看麦娘(ALOMY)、反枝苋(AMARE)、野燕麦(AVEFA)、马唐(DIGSA)、稗草(ECHCG)、无香母菊(MATIN)、圆叶牵牛(PHBPU)、卷茎蓼(POLCO)、狗尾草(SETVI)、阿拉伯婆婆纳(VERPE)和三色堇(VIOTR)。
Claims (13)
1.通式(I)的取代的杂芳基氧基吡啶或其盐
其中
R1为任选取代的5元杂芳基环,其任选被最高达3个独立地选自
R4的取代基取代,
R2独立地为卤素、羟基、氨基、氰基、硝基、甲酰基、甲酰胺、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-C4)-卤代烯基、(C2-C4)-卤代炔基、
(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷氧基、
(C1-C4)-烯氧基、(C1-C4)-炔氧基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C3-C6)-环烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C3-C6)-环烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C3-C6)-环烷基磺酰基、
(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-烷硫基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C3-C6)-环烷基羰基、羧基、(C1-C4)-烷氧基羰基、(C1-C4)-卤代烷氧基羰基、(C3-C6)-环烷氧基羰基、(C1-C4)-烷基氨基羰基、(C2-C6)-二烷基氨基羰基、(C3-C6)-环烷基氨基羰基、(C1-C4)-烷基羰基氨基、(C1-C4)-卤代烷基羰基氨基、(C2-C6)-环烷基羰基氨基、(C1-C4)-烷氧基羰基氨基、(C1-C4)-烷基氨基羰基氨基、(C2-C6)-二烷基氨基羰基氨基、羧基-(C1-C4))-烷基、(C1-C4)-烷氧基羰基-(C1-C4)-烷基、
(C1-C4)-卤代烷氧基羰基-(C1-C4)-烷基、(C3-C6)-环烷氧基羰基-(C1-C4)-烷基、(C1-C4)-烷基氨基磺酰基、(C2-C6)-二烷基氨基磺酰基或(C3-C6)-三烷基甲硅烷基,
n为0、1、2或3,
R3为卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,R4为氢、卤素、羟基、氨基、氰基、甲酰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C4)-烷基、(C1-C4)-烷基-(C3-C6)-环烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
X为N或CR5,
Y为N或CH,
和
R5为氢、卤素或氰基,
不包括其中R1为未取代的或取代的3-吡唑的化合物。
2.根据权利要求1所述的通式(I)的化合物或其盐,其中R1为基团R1-1至R1-42:
R2独立地为卤素、羟基、氨基、氰基、硝基、甲酰基、甲酰胺、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基、(C2-C4)-炔基、(C2-C4)-卤代烯基、(C2-C4)-卤代炔基、
(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷氧基、
(C1-C4)-烯氧基、(C1-C4)-炔氧基、(C1-C4)-烷硫基、(C1-C4)-卤代烷硫基、(C3-C6)-环烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-卤代烷基亚磺酰基、(C3-C6)-环烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-卤代烷基磺酰基、(C3-C6)-环烷基磺酰基、
(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷氧基-(C1-C4)-烷基、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C3-C6)-环烷基羰基、羧基、(C1-C4)-烷氧基羰基、(C1-C4)-卤代烷氧基羰基、
(C3-C6)-环烷氧基羰基、(C1-C4)-烷基氨基羰基、(C2-C6)-二烷基氨基羰基、(C3-C6)-环烷基氨基羰基、(C1-C4)-烷基羰基氨基、(C1-C4)-卤代烷基羰基氨基、(C2-C6)-环烷基羰基氨基、(C1-C4)-烷氧基羰基氨基或(C3-C6)-三烷基甲硅烷基,
n为0、1或2,
R3为卤素、氰基、硝基、(C1-C4)-烷基或(C1-C4)-卤代烷基,R4为氢、卤素、羟基、氨基、氰基、甲酰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基、(C1-C4)-烷氧基羰基、(C1-C4)-烷氧基硫代羰基、(C3-C6)-环烷基-(C1-C4)-烷基、(C1-C4)-烷基-(C3-C6)-环烷基或(C1-C4)-烷氧基-(C1-C4)-烷基,
R4a为氢或(C1-C2)-烷基,
X为N或CR5,
Y为N或CH,
和
R5为氢、卤素或氰基。
3.根据权利要求1所述的通式(I)的化合物或其盐,其中R1为如权利要求2所述的基团R1-1至R1-3,
R2独立地为氯、溴、氰基或甲基,
n为1或2,
R3为氟、氯、溴、氰基、硝基或三氟甲基,
R4为氢、氯、溴、碘、三氟甲基、二氟甲基、氯氟甲基、二氟氯甲基、二氯甲基、三氯甲基、二氟溴甲基、环丙基、环丙基甲基、(1-甲基)环丙基或甲氧基甲基,
X为N或CR5,
Y为N或CH,
和
R5为氢、氟、氯或氰基。
4.除草组合物,其特征在于含有除草活性量的至少一种如权利要求1至3中任一项所述的通式(I)的化合物。
5.根据权利要求4所述的除草组合物,其与制剂助剂混合。
6.根据权利要求4或5所述的除草组合物,其包含至少一种选自杀昆虫剂、杀螨剂、除草剂、杀真菌剂、安全剂和生长调节剂的其他农药活性物质。
7.根据权利要求6所述的除草组合物,其包含安全剂。
8.根据权利要求7所述的除草组合物,其包含环丙磺酰胺、解草酯、吡唑解草酯或双苯噁唑酸。
9.根据权利要求4至8中任一项所述的除草组合物,其包含其他除草剂。
10.防治不想要的植物的方法,其特征在于将有效量的至少一种如权利要求1至3中任一项所述的通式(I)的化合物或如权利要求4至9中任一项所述的除草组合物施用至植物或不想要的植物的位置。
11.根据权利要求1至3中任一项所述的通式(I)的化合物或根据权利要求4至9中任一项所述的除草组合物用于防治不想要的植物的用途。
12.根据权利要求11所述的用途,其特征在于将通式(I)的化合物用于防治有用植物作物中的不想要的植物。
13.根据权利要求12所述的用途,其特征在于有用植物为转基因有用植物。
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WO2023186691A1 (de) | 2022-03-28 | 2023-10-05 | Bayer Aktiengesellschaft | Substituierte 2-c-azine sowie deren salze und ihre verwendung als herbizide wirkstoffe |
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