CN115943143A - 1-吡嗪基吡唑基-3-氧基烷基酸和其衍生物及其用于控制不需要的植物生长的用途 - Google Patents
1-吡嗪基吡唑基-3-氧基烷基酸和其衍生物及其用于控制不需要的植物生长的用途 Download PDFInfo
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- CN115943143A CN115943143A CN202180043542.5A CN202180043542A CN115943143A CN 115943143 A CN115943143 A CN 115943143A CN 202180043542 A CN202180043542 A CN 202180043542A CN 115943143 A CN115943143 A CN 115943143A
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- 238000002360 preparation method Methods 0.000 claims abstract description 12
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- 125000000217 alkyl group Chemical group 0.000 claims description 63
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- 230000001105 regulatory effect Effects 0.000 claims description 5
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 2
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- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 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
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 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
- 229940072651 tylenol Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 241000228158 x Triticosecale Species 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Abstract
本发明涉及通式(I)的新型、除草有效的取代的1‑吡嗪基吡唑基‑3‑氧基烷基酸和其衍生物及它们的农用化学上可接受的盐、N‑氧化物、水合物以及所述盐和N‑氧化物的水合物,其制备方法及其用于防治有用植物作物中的杂草和禾本科杂草(weed grasses)以及用于一般性控制不希望植物生长的环境区域中的杂草和禾本科杂草的用途。
Description
本发明涉及通式(I)的新型、除草活性的取代的1-吡嗪基吡唑基-3-氧基烷基酸和其衍生物及它们的农用化学上相容的/可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其制备方法及其用于防治有用植物作物中的阔叶杂草和禾本科杂草(weedgrasses)以及用于一般性防治植物生长造成麻烦的环境区域中的阔叶杂草和禾本科杂草的用途。
1-吡嗪基吡唑基-3-氧基烷基酸的衍生物特别包括其酯、盐和酰胺。
现有技术公开了取代的1,5-二苯基吡唑基-3-氧基乙酸和取代的1-苯基-5-噻吩基吡唑基-3-氧基烷基酸的生物学作用及制备这些化合物的方法。DE 2828529 A1描述了1,5-二苯基吡唑基-3-氧基乙酸的制备和降脂作用。CN 101284815公开了作为具有杀细菌活性农用化学品的1,5-二苯基吡唑基-3-氧基乙酸衍生物。WO 2008/083233 A2描述了1,5-二苯基吡唑基-3-氧基烷基酸及其衍生物作为适于使细胞聚集物散开的物质。Journal ofHeterocyclic Chemistry(2012),49(6),1370-1375进一步描述了1,5-二苯基吡唑基-3-氧基乙酸的合成和杀真菌作用。WO 2008/073825 A1中描述了取代的1-苯基-5-噻吩基吡唑基-3-氧基烷基酸的合成及其作为FXR和LXR调节剂的药学作用。
本发明的1-吡嗪基吡唑基-3-氧基烷基酸及其衍生物与先前已知的1,5-二苯基吡唑基-3-氧代乙酸和1-苯基-5-噻吩基吡唑基-3-氧基烷基酸的不同在于吡唑环的1位的吡嗪基基团,并因此迄今未知。
本发明的一个目的是提供新型吡唑衍生物,其可用作除草剂或植物生长调节剂,具有令人满意的除草作用和对有害植物的广谱活性和/或在有用植物的作物中具有高选择性。
此目的通过在吡唑环的1位具有吡嗪基取代基的取代的吡唑基-3-氧基烷基酸来实现,即通过1-吡嗪基吡唑基-3-氧基烷基酸衍生物来实现,其具有非常好的除草作用以及非常好的选择性。
令人惊奇的是,这些化合物对广泛的经济上重要的禾本科杂草和阔叶杂草非常有效。同时,这些化合物表现出良好的作物植物相容性。因此,鉴于对有害植物的良好功效,它们可选择性地用于作物植物中。
本发明提供了通式(I)的1-吡嗪基吡唑基-3-氧基烷基酸
及其农用化学上相容的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中基团如下定义:
A为A1-A28:
R1为
-OR1a或
-NR9R10,其中
R1a
-为氢;
-为(C1-C12)-烷基,其未被取代或者被一个或多个选自卤素、
(C3-C6)-环烷基、(C1-C4)-三烷基甲硅烷基、(C1-C6)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、氰基和硝基的取代基所取代;
-为(C2-C6)-烯基、(C2-C6)-卤代烯基;
-为(C2-C6)-炔基;
-为(C3-C6)-环烷基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C3-C6)-环烷基的取代基所取代;
-为(C1-C4)-烷基-SO-(C1-C4)-烷基、(C1-C4)-烷基-SO2-(C1-C4)-烷基;
-为杂环基、杂芳基和芳基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为杂环基-(C1-C4)-烷基、杂芳基-(C1-C4)-烷基和芳基-(C1-C4)-烷基,其中所述杂环基、杂芳基和芳基未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为(C1-C6)-亚烷基氨基;
R9为氢和(C1-C12)-烷基;
R10
-为氢;
-为芳基、杂芳基、杂环基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为(C3-C7)-环烷基-(C1-C4)-烷基、杂环基-(C1-C4)-烷基、杂芳基-(C1-C4)-烷基、芳基-(C1-C4)-烷基、芳基-(C1-C4)-烷氧基;
其中所述环烷基、杂环基、杂芳基和芳基未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-(C1-C12)-烷基;(C3-C8)-环烷基、(C2-C12)-烯基、(C5-C8)-环烯基、(C2-C12)-炔基;
其中上述烷基、环烷基、烯基、环烯基和炔基基团未被取代或各自独立地被m个选自氰基、硝基、OR5、S(O)nR5、SO2NR6R7、C(O)OR8、CONR6R8、COR6、NR6R8、NR6COR8、NR6CONR8R8、NR6CO2R8、NR6SO2R8、NR6SO2NR6R8、C(R6)=NOR8的基团所取代;
-为(C1-C12)-卤代烷基;
-为S(O)nR5、氰基、硝基、OR5、SO2NR6R7、CO2R8、COR8、NR6R8、NR6COR8、NR6CO2R8、NR6SO2R8;
或
R9和R10与它们所键合的氮原子一起形成饱和的或者部分或完全不饱和的五元、六元或七元环,所述环任选被选自卤素、(C1-C6)-烷基、卤素-(C1-C6)-烷基、OR5、S(O)nR5、CO2R8、CONR6R8、COR6和C(R6)=NOR8的基团单取代至六取代,并且,除该氮原子外,所述环还含有r个碳原子、o个氧原子、p个硫原子和q个来自NR7、CO和NCOR7的元素作为环原子;
R5为(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基、(C2-C4)-烯基或芳基;
R6为氢或R5;
R7为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C4)-烯基或(C3-C4)-炔基;
R8为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C4)-烯基或(C3-C4)-炔基;
R2a为
-氢、卤素、氰基;
-(C1-C6)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C3-C6)-环烷基;
R2b为
-氢和(C1-C4)-烷基;
R3为
-卤素、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C4)-烷氧基羰基;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-(C1-C2)-烷基-S(O)n和(C1-C2)-卤代烷基-S(O)n;
-CHO、C(O)NH2;
-NH2;
R4为
-卤素、氰基、异氰基、硝基;
-(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷基、(C1-C3)-卤代烷氧基;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-(C1-C4)-烷基-S(O)n、(C1-C4)-卤代烷基-S(O)n;
-CHO、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C1-C4)-烷氧基羰基;
-NH2;
R12为
-卤素、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C4)-烷氧基羰基、(C1-C6)-烷氧基、(C1-C3)-卤代烷氧基、(C1-C4)-烷基-S(O)n;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-NH2;
并且其中指数如下:
l为0、1、2或3;
m为0、1或2;
n为0、1或2;
o为0、1或2;
p为0或1;
q为0或1;
r为3、4、5或6;和
s为0、1、2、3、4或5。
定义
在上式中使用的符号的定义中,使用了统称,其通常代表以下取代基:
卤素:氟、氯、溴或碘,优选氟、氯或溴,并且更优选氟或氯。
烷基:具有1至12个、优选1至6个、并且更优选1至4个碳原子的饱和直链或支链烃基团,例如(但不限于)C1-C6-烷基如甲基、乙基、丙基(正丙基)、1-甲基乙基(异丙基)、丁基(正丁基)、1-甲基丙基(仲丁基)、2-甲基丙基(异丁基)、1,1-二甲基乙基(叔丁基)、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、1,1-二甲基丙基、1,2-二甲基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基和1-乙基-2-甲基丙基。特别地,该基团为C1-C4-烷基基团,例如,甲基、乙基、丙基、1-甲基乙基(异丙基)、丁基、1-甲基丙基(仲丁基)、2-甲基丙基(异丁基)或1,1-二甲基乙基(叔丁基)基团。除非另有定义,否则,例如对于烷基硫烷基、烷基亚磺酰基、烷基磺酰基、卤代烷基或卤代烷基硫烷基,该定义也适用于作为复合取代基的一部分的烷基,例如环烷基烷基或羟烷基。
烯基:具有2至8个、优选2至6个、并且更优选2至4个碳原子和在任何位置的双键的不饱和直链或支链烃基团,例如(但不限于)C2-C6-烯基,如乙烯基、烯丙基、(E)-2-甲基乙烯基、(Z)-2-甲基乙烯基、异丙烯基、高烯丙基、(E)-丁-2-烯基、(Z)-丁-2-烯基、(E)-丁-1-烯基、(Z)-丁-1-烯基、2-甲基丙-2-烯基、1-甲基丙-2-烯基、2-甲基丙-1-烯基、(E)-1-甲基丙-1-烯基、(Z)-1-甲基丙-1-烯基、戊-4-烯基、(E)-戊-3-烯基、(Z)-戊-3-烯基、(E)-戊-2-烯基、(Z)-戊-2-烯基、(E)-戊-l-烯基、(Z)-戊-l-烯基、3-甲基丁-3-烯基、2-甲基丁-3-烯基、1-甲基丁-3-烯基、3-甲基丁-2-烯基、(E)-2-甲基丁-2-烯基、(Z)-2-甲基丁-2-烯基、(E)-1-甲基丁-2-烯基、(Z)-1-甲基丁-2-烯基、(E)-3-甲基丁-1-烯基、(Z)-3-甲基丁-1-烯基、(E)-2-甲基丁-1-烯基、(Z)-2-甲基丁-1-烯基、(E)-1-甲基丁-1-烯基、(Z)-1-甲基丁-1-烯基、1,1-二甲基丙-2-烯基、1-乙基丙-1-烯基、1-丙基乙烯基、1-异丙基乙烯基、(E)-3,3-二甲基丙-1-烯基、(Z)-3,3-二甲基丙-1-烯基、己-5-烯基、(E)-己-4-烯基、(Z)-己-4-烯基、(E)-己-3-烯基、(Z)-己-3-烯基、(E)-己-2-烯基、(Z)-己-2-烯基、(E)-己-l-烯基、(Z)-己-l-烯基、4-甲基戊-4-烯基、3-甲基戊-4-烯基、2-甲基戊-4-烯基、1-甲基戊-4-烯基、4-甲基戊-3-烯基、(E)-3-甲基戊-3-烯基、(Z)-3-甲基戊-3-烯基、(E)-2-甲基戊-3-烯基、(Z)-2-甲基戊-3-烯基、(E)-1-甲基戊-3-烯基、(Z)-1-甲基戊-3-烯基、(E)-4-甲基戊-2-烯基、(Z)-4-甲基戊-2-烯基、(E)-3-甲基戊-2-烯基、(Z)-3-甲基戊-2-烯基、(E)-2-甲基戊-2-烯基、(Z)-2-甲基戊-2-烯基、(E)-1-甲基戊-2-烯基、(Z)-1-甲基戊-2-烯基、(E)-4-甲基戊-1-烯基、(Z)-4-甲基戊-1-烯基、(E)-3-甲基戊-1-烯基、(Z)-3-甲基戊-1-烯基、(E)-2-甲基戊-1-烯基、(Z)-2-甲基戊-1-烯基、(E)-1-甲基戊-1-烯基、(Z)-1-甲基戊-1-烯基、3-乙基丁-3-烯基、2-乙基丁-3-烯基、1-乙基丁-3-烯基、(E)-3-乙基丁-2-烯基、(Z)-3-乙基丁-2-烯基、(E)-2-乙基丁-2-烯基、(Z)-2-乙基丁-2-烯基、(E)-1-乙基丁-2-烯基、(Z)-1-乙基丁-2-烯基、(E)-3-乙基丁-1-烯基、(Z)-3-乙基丁-1-烯基、2-乙基丁-1-烯基、(E)-1-乙基丁-1-烯基、(Z)-1-乙基丁-1-烯基、2-丙基丙-2-烯基、1-丙基丙-2-烯基、2-异丙基丙-2-烯基、1-异丙基丙-2-烯基、(E)-2-丙基丙-1-烯基、(Z)-2-丙基丙-1-烯基、(E)-1-丙基丙-1-烯基、(Z)-1-丙基丙-1-烯基、(E)-2-异丙基丙-1-烯基、(Z)-2-异丙基丙-1-烯基、(E)-1-异丙基丙-1-烯基、(Z)-1-异丙基丙-1-烯基、1-(1,1-二甲基乙基)乙烯基、丁-1,3-二烯基、戊-1,4-二烯基、己-1,5-二烯基或甲基己二烯基。特别地,该基团为乙烯基或烯丙基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的烯基,例如卤代烯基。
炔基:具有2至8个、优选2至6个、并且更优选2至4个碳原子和在任何位置的三键的直链或支链烃基团,例如(但不限于)C2-C6-炔基,如乙炔基、丙-1-炔基、丙-2-炔基、丁-1-炔基、丁-2-炔基、丁-3-炔基、1-甲基丙-2-炔基、戊-1-炔基、戊-2-炔基、戊-3-炔基、戊-4-炔基、2-甲基丁-3-炔基、1-甲基丁-3-炔基、1-甲基丁-2-炔基、3-甲基丁-1-炔基、1-乙基丙-2-炔基、己-1-炔基、己-2-炔基、己-3-炔基、己-4-炔基、己-5-炔基、3-甲基戊-4-炔基、2-甲基戊-4-炔基、1-甲基戊-4-炔基、2-甲基戊-3-炔基、1-甲基戊-3-炔基、4-甲基戊-2-炔基、1-甲基戊-2-炔基、4-甲基戊-1-炔基、3-甲基戊-1-炔基、2-乙基丁-3-炔基、1-乙基丁-3-炔基、1-乙基丁-2-炔基、1-丙基丙-2-炔基、1-异丙基丙-2-炔基、2,2-二甲基丁-3-炔基、1,1-二甲基丁-3-炔基、1,1-二甲基丁-2-炔基或3,3-二甲基丁-1-炔基。特别地,所述炔基基团为乙炔基、丙-1-炔基或丙-2-炔基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的炔基,例如卤代炔基。
烷氧基:具有1至8个、优选1至6个、并且更优选1至4个碳原子的饱和直链或支链烷氧基基团,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、2,2-二甲基丙氧基、1-乙基丙氧基、1,1-二甲基丙氧基、1,2-二甲基丙氧基、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。除非另有定义,否则该定义也适用于作为复合取代基的一部分的烷氧基,例如卤代烷氧基、炔基烷氧基。
烷氧基羰基:具有1至8个、优选1至6个、并且更优选1至4个碳原子并经由羰基基团(-CO-)键合至骨架的烷氧基基团(如上文所指定)。除非另有定义,否则该定义也适用于作为复合取代基的一部分的烷氧基羰基,例如环烷基烷氧基羰基。
环烷基:具有3至10个、优选3至8个、并且更优选3至6个碳环成员的单环饱和烃基基团,例如(但不限于)环丙基、环戊基和环己基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的环烷基,例如环烷基烷基。
环烯基:具有3至10个、优选3至8个、并且更优选3至6个碳环成员的单环的部分不饱和烃基基团,例如(但不限于)环丙烯基、环戊烯基和环己烯基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的环烯基,例如环烯基烷基。
环烷氧基:具有3至10个、优选3至8个、并且更优选3至6个碳环成员的单环饱和烃基基团,例如(但不限于)环丙氧基、环戊氧基和环己氧基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的环烷氧基,例如环烷氧基烷基。
卤代烷基:具有1至6个、优选1至4个碳原子的直链或支链烷基基团(如上所述),其中这些基团中的一些或全部氢原子被替换为如上所述的卤素原子,例如(但不限于)C1-C3-卤代烷基如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基和1,1,1-三氟丙-2-基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的卤代烷基,例如卤代烷基氨基烷基。
卤代烯基和卤代炔基的定义类似于卤代烷基,不同之处在于,烯基和炔基基团,而不是烷基基团,分别作为取代基的一部分存在。
卤代烷氧基:具有1至6个、优选1至3个碳原子的直链或支链烷氧基基团(如上所述),其中这些基团中的一些或全部氢原子被替换为如上所述的卤素原子,例如(但不限于)C1-C3-卤代烷氧基如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基、五氟乙氧基和1,1,1-三氟丙-2-氧基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的卤代烷氧基,例如卤代烷氧基烷基。
芳基:具有6至14个碳原子的单环、双环或三环芳族或部分芳族基团,例如(但不限于)苯基、萘基、四氢萘基、茚基和茚满基。与母体一般结构的键可经由芳基基团的任何所需的合适环成员。芳基优选选自苯基、1-萘基和2-萘基。特别优选苯基。
杂芳基:具有至少1个杂原子抑或任选地2、3、4或5个杂原子的5-或6-元环状芳族基团,其中杂原子各自独立地选自S、N和O,其中所述基团也可以是具有至多14个环成员的双环或三环系统的一部分,其中所述环系统可与一个或两个另外的环烷基、环烯基、杂环基、烯丙基和/或杂芳基基团形成,并且其中优选的是苯并稠合的5-或6-元杂芳基基团。与母体一般结构的键合可经由杂芳基基团的任何所需的合适环成员。经由碳环成员之一键合至骨架的5-元杂芳基基团的实例是呋喃-2-基、呋喃-3-基、噻吩-2-基、噻吩-3-基、吡咯-2-基、吡咯-3-基、异噁唑-3-基、异噁唑-4-基、异噁唑-5-基、异噻唑-3-基、异噻唑-4-基、异噻唑-5-基、吡唑-3-基、吡唑-4-基、吡唑-5-基、噁唑-2-基、噁唑-4-基、噁唑-5-基、噻唑-2-基、噻唑-4-基、噻唑-5-基、咪唑-2-基、咪唑-4-基、1,2,4-噁二唑-3-基、1,2,4-噁二唑-5-基、1,2,4-噻二唑-3-基、1,2,4-噻二唑-5-基、1,2,4-三唑-3-基、1,3,4-噁二唑-2-基、1,3,4-噻二唑-2-基和1,3,4-三唑-2-基。经由氮环成员键合至骨架的5-元杂芳基基团的实例是吡咯-1-基、吡唑-1-基、1,2,4-三唑-1-基、咪唑-1-基、1,2,3-三唑-1-基和1,3,4-三唑-1-基。6-元杂芳基基团的实例是吡啶-2-基、吡啶-3-基、吡啶-4-基、哒嗪-3-基、哒嗪-4-基、嘧啶-2-基、嘧啶-4-基、嘧啶-5-基、吡嗪-2-基、1,3,5-三嗪-2-基、1,2,4-三嗪-3-基和1,2,4,5-四嗪-3-基。苯并稠合的5-元杂芳基基团的实例是吲哚-1-基、吲哚-2-基、吲哚-3-基、吲哚-4-基、吲哚-5-基、吲哚-6-基、吲哚-7-基、苯并咪唑-1-基、苯并咪唑-2-基、苯并咪唑-4-基、苯并咪唑-5-基、吲唑-1-基、吲唑-3-基、吲唑-4-基、吲唑-5-基、吲唑-6-基、吲唑-7-基、吲唑-2-基、1-苯并呋喃-2-基、1-苯并呋喃-3-基、1-苯并呋喃-4-基、1-苯并呋喃-5-基、1-苯并呋喃-6-基、1-苯并呋喃-7-基、1-苯并噻吩-2-基、1-苯并噻吩-3-基、1-苯并噻吩-4-基、1-苯并噻吩-5-基、1-苯并噻吩-6-基、1-苯并噻吩-7-基、1,3-苯并噻唑-2-基、1,3-苯并噻唑-4-基、1,3-苯并噻唑-5-基、1,3-苯并噻唑-6-基、1,3-苯并噻唑-7-基、1,3-苯并噁唑-2-基、1,3-苯并噁唑-4-基、1,3-苯并噁唑-5-基、1,3-苯并噁唑-6-基和1,3-苯并噁唑-7-基。苯并稠合的6-元杂芳基基团的实例是喹啉-2-基、喹啉-3-基、喹啉-4-基、喹啉-5-基、喹啉-6-基、喹啉-7-基、喹啉-8-基、异喹啉-1-基、异喹啉-3-基、异喹啉-4-基、异喹啉-5-基、异喹啉-6-基、异喹啉-7-基和异喹啉-8-基。作为双环环系统的一部分的5-或6-元杂芳基基团的进一步实例是1,2,3,4-四氢喹啉-1-基、1,2,3,4-四氢喹啉-2-基、1,2,3,4-四氢喹啉-7-基、1,2,3,4-四氢喹啉-8-基、1,2,3,4-四氢异喹啉-1-基、1,2,3,4-四氢异喹啉-2-基、1,2,3,4-四氢异喹啉-5-基、1,2,3,4-四氢异喹啉-6-基和1,2,3,4-四氢异喹啉-7-基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的杂芳基,例如杂芳基烷基。
杂环基:具有至少一个、任选地至多四个独立地选自N、O、S、S(=O)、S(=O)2和二-(C1-C4)烷基甲硅烷基的杂原子和/或杂基团的三至七元饱和或部分不饱和杂环基团,其中所述基团可以是苯并稠合的。与母体一般结构的键可经由环碳原子,或者如果可能,经由杂环基团的环氮原子。在此上下文中,饱和杂环基团为例如(但不限于)氧杂环丙烷基、氮杂环丙烷基、四氢呋喃-2-基、四氢呋喃-3-基、四氢噻吩-2-基、四氢噻吩-3-基、吡咯烷-2-基、吡咯烷-3-基、异噁唑烷-3-基、异噁唑烷-4-基、异噁唑烷-5-基、异噻唑烷-3-基、异噻唑烷-4-基、异噻唑烷-5-基、吡唑烷-3-基、吡唑烷-4-基、吡唑烷-5-基、噁唑烷-2-基、噁唑烷-4-基、噁唑烷-5-基、噻唑烷-2-基、噻唑烷-4-基、噻唑烷-5-基、咪唑烷-2-基、咪唑烷-4-基、1,2,4-噁二唑烷-3-基、1,2,4-噁二唑烷-5-基、1,3,4-噁二唑烷-2-基、1,2,4-噻二唑烷-3-基、1,2,4-噻二唑烷-5-基、1,3,4-噻二唑烷-2-基、1,2,4-三唑烷-3-基、1,3,4-三唑烷-2-基、哌啶-2-基、哌啶-3-基、哌啶-4-基、1,3-二噁烷-5-基、四氢吡喃-2-基、四氢吡喃-4-基、四氢噻吩-2-基、六氢哒嗪-3-基、六氢哒嗪-4-基、六氢嘧啶-2-基、六氢嘧啶-4-基、六氢嘧啶-5-基、哌嗪-2-基、1,3,5-六氢三嗪-2-基和1,2,4-六氢三嗪-3-基。在此上下文中,部分不饱和杂环基团为例如(但不限于)2,3-二氢呋喃-2-基、2,3-二氢呋喃-3-基、2,4-二氢呋喃-2-基、2,4-二氢呋喃-3-基、2,3-二氢噻吩-2-基、2,3-二氢噻吩-3-基、2,4-二氢噻吩-2-基、2,4-二氢噻吩-3-基、2-吡咯啉-2-基、2-吡咯啉-3-基、3-吡咯啉-2-基、3-吡咯啉-3-基、2-异噁唑啉-3-基、3-异噁唑啉-3-基、4-异噁唑啉-3-基、2-异噁唑啉-4-基、3-异噁唑啉-4-基、4-异噁唑啉-4-基、2-异噁唑啉-5-基、3-异噁唑啉-5-基、4-异噁唑啉-5-基、2-异噻唑啉-3-基、3-异噻唑啉-3-基、4-异噻唑啉-3-基、2-异噻唑啉-4-基、3-异噻唑啉-4-基、4-异噻唑啉-4-基、2-异噻唑啉-5-基、3-异噻唑啉-5-基、4-异噻唑啉-5-基、2,3-二氢吡唑-1-基、2,3-二氢吡唑-2-基、2,3-二氢吡唑-3-基、2,3-二氢吡唑-4-基、2,3-二氢吡唑-5-基、3,4-二氢吡唑-1-基、3,4-二氢吡唑-3-基、3,4-二氢吡唑-4-基、3,4-二氢吡唑-5-基、4,5-二氢吡唑-1-基、4,5-二氢吡唑-3-基、4,5-二氢吡唑-4-基、4,5-二氢吡唑-5-基、2,3-二氢噁唑-2-基、2,3-二氢噁唑-3-基、2,3-二氢噁唑-4-基、2,3-二氢噁唑-5-基、3,4-二氢噁唑-2-基、3,4-二氢噁唑-3-基、3,4-二氢噁唑-4-基、3,4-二氢噁唑-5-基、3,4-二氢噁唑-2-基、3,4-二氢噁唑-3-基、3,4-二氢噁唑-4-基。苯并稠合的杂环基团的实例是吲哚啉-1-基、吲哚啉-2-基、吲哚啉-3-基、异吲哚啉-1-基、异吲哚啉-2-基、2,3-二氢苯并呋喃-2-基和2,3-二氢苯并呋喃-3-基。除非另有定义,否则该定义也适用于作为复合取代基的一部分的杂环基,例如杂环基烷基。
不包括违反自然规律的组合,因此本领域技术人员会基于他们的专业知识排除这些组合。例如,排除具有三个或更多个相邻氧原子的环结构。
优选通式(I)的化合物及其农用化学上相容的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中基团如下定义:
A为A1-A16:
R1为
-OR1a或
-NR9R10,其中
R1a
-为氢;
-为(C1-C6)-烷基,其未被取代或者被一个或多个选自卤素、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C2)-烷氧基-(C1-C4)-烷氧基、氰基和硝基的取代基所取代;
-为(C2-C6)-烯基、(C2-C6)-卤代烯基;
-为芳基-(C1-C2)-烷基、杂芳基-(C1-C2)-烷基,其中所述芳基和杂芳基未被取代或者被一个或多个选自卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基的取代基所取代;
-为(C1-C4)-亚烷基氨基;
R9为氢和(C1-C6)-烷基;
R10
-为氢;
-为(C3-C7)-环烷基-(C1-C4)-烷基、芳基-(C1-C4)-烷基、芳基
-(C1-C4)-烷氧基,
其中所述环烷基和芳基未被取代或者被一个或多个选自卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基的取代基所取代;
-为(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基;(C3-C8)-环烷基;其中上述烷基、环烷基、烯基、环烯基和炔基基团未被取代或各自独立地被m个选自以下的基团所取代:
氰基、C(O)OR8;
-为(C1-C6)-卤代烷基;
-为S(O)2R5、SO2NR6R7、NR6SO2R8;
R5为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基或芳基;
R6为氢、(C1-C4)-烷基或(C3-C6)-环烷基;
R7为氢、(C1-C4)-烷基或(C3-C6)-环烷基;
R8为氢、(C1-C6)-烷基、(C3-C6)-环烷基;
R2a为
-氢、氰基;
-(C1-C6)-烷基;
-(C3-C6)-环烷基;
R2b为氢;
R3为
-氟、氯、溴、碘、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基;
R4为
-氟、氯、溴、氰基;
-甲基、乙基;
-甲氧基、乙氧基;
R12为
-卤素、氰基、硝基;
-甲基、乙基、(C1-C2)-卤代烷基;
-甲氧基、乙氧基;
并且其中指数如下:
l为0、1或2;
m为0、1或2;
s为0、1、2、3。
特别优选通式(I)的化合物及其农用化学上相容的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中基团如下定义:
A为A1-A10:
R1为
-OR1a或
-NR9R10,其中
R1a
-为氢;
-为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为1-丙烯基、2-丙烯基;
-为苄基、吡啶基甲基,其中苯基和吡啶基基团在每种情况下未被取代或被卤素所取代;
-为异亚丙基氨基;
R9为氢;
R10
-为氢;
-为环丙基甲基;
-为苄基、1-苯基乙基、2-苯基乙基、苄氧基,其中所述四个基团的每一个中的苯基基团未被取代或被卤素所取代;
-为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基,其中上述基团未被取代或被C(O)OR8基团单取代;
-为环丙基、环丁基、环戊基,其中所述三个基团未被取代或被C(O)OR8基团单取代;
-为1-丙烯基、2-丙烯基、2-甲基-2-丙烯基、丙-2-炔-1-基、丁-2-炔-1-基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、丙基、1-甲基乙基、三氟甲基、1,1-二氟乙基、2,2,2-三氟乙基、环丙基或乙烯基;
R6为氢、甲基、乙基、丙基、1-甲基乙基或环丙基;
R7为氢或甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3为
-氟、氯、溴、碘、氰基、NO2;
-环丙基、三氟甲基;
R4为
-氟、氯、溴;
-甲基;
R12为
-氟、氯、溴;
并且其中指数如下:
l为0或1;
s为0、1或2。
非常特别优选通式(I)的化合物及其农用化学上相容的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中基团如下定义:
A为A1、A3、A4、A5或A6:
R1为
-OR1a或
-NR9R10,其中
R1a
-为氢;
-为甲基、乙基;
-为氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为吡啶-2-基甲基;
-为异亚丙基氨基;
R9为氢;
R10
-为被C(O)OR8单取代的环戊基;
-为环丙基甲基;
-为CH2C(O)OR8、CH2CH2C(O)OR8;
-为2-丙烯基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、三氟甲基、1,1-二氟乙基、环丙基或乙烯基;
R6为甲基、乙基、丙基或1-甲基乙基;
R7为氢或甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3选自
-氯、溴、碘、氰基、NO2;
-为三氟甲基、环丙基;
R4为
-氟、氯;
R12为氟;
并且其中指数如下:
l为0或1;
s为0、1或2。
最优选通式(I)的化合物及其农用化学上相容的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中基团如下定义:
A为A1-1、A1-2、A1-3、A3-1、A3-2、A3-3、A3-4、A4-1、A5-1或A5-2:
R1为
-OR1a或
-NR9R10,其中
R1a
-为氢;
-为甲基、乙基;
-为氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为吡啶-2-基甲基;
-为异亚丙基氨基;
R9为氢;
R10
-为被C(O)OR8单取代的环戊基;
-为环丙基甲基;
-为CH2C(O)OR8、CH2CH2C(O)OR8;
-为2-丙烯基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、三氟甲基、环丙基或乙烯基;
R6为甲基、乙基或1-甲基乙基;
R7为甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3为
-氯、溴、氰基、环丙基;
R4为
-3-氟、3-氯;
其中指数
l为0或1。
本发明优选还提供了通式(Ix)的化合物及其农用化学上相容的盐、N-氧化物、水合物及所述盐和N-氧化物的水合物,其中R1、R3、R4、A和l基团符合上述优选、特别优选、非常特别优选和最优选的定义:
本发明优选还提供了通式(Iy)的化合物及其农用化学上相容的盐、N-氧化物、水合物及所述盐和N-氧化物的水合物,其中R1、R3、R4、A和l基团符合上述优选、特别优选、非常特别优选和最优选的定义:
本发明优选还提供了通式(Iz)的化合物及其农用化学上相容的盐、N-氧化物、水合物及所述盐和N-氧化物的水合物,其中R1、R2a、R2b、R3和A基团符合上述优选、特别优选、非常特别优选和最优选的定义:
如果化合物可通过氢位移形成其结构在形式上不被通式(I)覆盖的互变异构体,则这些互变异构体仍然为本发明的通式(I)的化合物的定义所涵盖,除非在考虑中的是特定的互变异构体。例如,许多羰基化合物可以酮形式和烯醇形式两者存在,这两种形式均为通式(I)的化合物的定义所涵盖。
通式(I)的本发明化合物可在烷基酸结构的第二个碳处具有手性碳原子,其在下面示出的结构中由标记(*)指示:
根据Cahn、Ingold和Prelog规则(CIP规则),该碳原子可具有(R)构型或(S)构型。
本发明涵盖通式(I)的化合物,包括(S)和(R)构型两者。
此外,本发明的范围还涵盖具有(R)构型的通式(I)的化合物(通式(I-R)的化合物)与具有(S)构型的通式(I)的化合物(通式(I-S)的化合物)的任何混合物,本发明还涵盖具有(R)和(S)构型的通式(I)的化合物的外消旋混合物。
然而,在本发明的上下文内,特别优选具有(R)构型的通式(I)的化合物,其具有60至100%、优选80至100%、尤其是90至100%、非常特别是95至100%的选择性,其中特定的(R)化合物在每种情况下以大于50%ee、优选60至100%ee、尤其是80至100%ee、非常特别是90至100%ee、最优选95至100%ee的对映选择性存在,基于所讨论的(R)化合物的总含量。
本发明因此更特别地涉及通式(I*)的化合物,其中(*)标记的碳原子上的立体化学构型以60至100%(R)、优选80至100%(R)、尤其是90至100%(R)、非常特别是95至100%(R)的立体化学纯度存在。
另外,取决于所选择的相应基团,通式(I)的本发明化合物中可能存在其他立体元素。
优选下表中列出的化合物。具有(R)构型的通式(I)的化合物在列出基团R2a的栏中相应地标记。例如,如果R2a=烷基,则在通式(I)的(*)标记的碳原子处的优选立体化学构型为(R)构型。
考虑到Cahn、Ingold和Prelog规则,在(*)标记的碳原子处,由于所讨论的取代基的优先级,故也可能存在其中在(*)标记的碳原子处优选(S)构型的情况。例如,当R2a基团对应于(C1-C6)-烷氧基基团时,就是这种情况。
因此,在本发明的范围内,尤其优选其空间排列对应于具有(R)构型的R2a=甲基的那些通式(I)化合物的通式(I)的化合物,具有60%至100%、优选80%至100%、尤其是90%至100%、非常特别是95%至100%的选择性,相应的(R)-类似化合物在每种情况下以大于50%ee、优选60%至100%ee、尤其是80%至100%ee、非常特别是90%至100%ee、最优选95%至100%ee的对映选择性存在,其中基于所讨论的(R)-类似化合物的总含量。因此,本发明更特别地涉及通式(I)的化合物,其中(*)标记的碳原子上的立体化学构型以60%至100%(R或R类似物)、优选80%至100%(R或R类似物)、尤其是90%至100%(R或R类似物)、非常特别是95%至100%(R或R类似物)的立体化学纯度存在。
表1:酯
表2:酰胺
本发明的又一个方面涉及通式(I)的本发明化合物的制备。本发明的化合物可以多种方式制备。
本发明的化合物可例如通过下面方案1中所示的合成方法由取代的1-吡嗪基-1H-吡唑-3-醇(II)制备。
方案1
方案1描述了通过通式(IV)的取代吡唑与通式(V)的亲电卤化试剂例如N-氯代琥珀酰亚胺((V),R3=Cl)、N-溴代琥珀酰亚胺((V),R3=Br)或N-碘代琥珀酰亚胺((V),R3=I)的反应合成通式((Ia),R3=Cl、Br、I)的化合物。以类似的方式,也可以使用其他亲电试剂,例如亲电硝化试剂如硝化酸、四氟硼酸硝鎓或硝酸铵/三氟乙酸(当R3=NO2时)或亲电氟化试剂如DAST、Selectfluor或N-氟代苯磺酰亚胺(当R3=F时)。该反应优选在0℃至120℃的温度范围内在适宜的溶剂例如N,N-二甲基甲酰胺、1,2-二氯乙烷或乙腈中进行。
通式(Ib;R3=CN)的化合物可例如加入适宜的量的过渡金属催化剂尤其是钯催化剂如四(三苯基膦)钯(0)或二乙酸钯或双(三苯基膦)二氯化钯(II)或者镍催化剂如乙酰丙酮镍(II)或双(三苯基膦)氯化镍(II)的情况下,优选在升高的温度下在有机溶剂例如1,2-二甲氧基乙烷或N,N-二甲基甲酰胺中通过在合适溶剂中的式(Ia;R3=Cl、Br、I,优选地R3=Br、I)的化合物与金属氰化物M-CN(V)的反应制备。“M”基团代表例如镁、锌、锂或钠。通常合适的交叉偶联方法有R.D.Larsen,Organometallics in Process Chemistry2004Springer Verlag;I.Tsuji,Palladium Reagents and Catalysts 2004Wiley;和M.Beller,C.Bolm,Transition Metals for Organic Synthesis 2004VCH-Wiley中描述的那些。其他合适的合成方法描述于Chem.Rev.2006,106,2651;Platinum Metals Review,2009,53,183;Platinum Metals Review 2008,52,172;和Acc.Chem.Res.2008,41,1486中。
通式(IV)的化合物的合成可通过通式(II)的3-羟基吡唑与通式(III)的卤化物在碱的存在下通过本领域技术人员已知的方法或类似于本领域技术人员已知的方法的烷基化来进行。作为碱,优选选自锂、钠、钾和铯的碱金属的碳酸盐。该反应优选在室温至150℃的温度范围内在适宜的溶剂例如二氯甲烷、乙腈、N,N-二甲基甲酰胺或二碘甲烷中进行。参见J.Med.Chem.2011,54(16),5820-5835和WO2010/010154。“X”基团代表例如氯、溴或碘。
通式(II)的3-羟基吡唑可例如类似于文献中已知的方法分两个阶段由通式(VII)的取代丙炔酸衍生物制备(方案2;参见例如:Adv.Synth.Catal.2014,356,3135-3147)。
方案2
在第一步(方案2)中,经由通式(VII)的取代丙炔酸与通式(VIII)的肼并吡嗪在酰胺偶联试剂例如丙烷膦酸酐(T3P)、二环己基碳二亚胺、N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺、N,N′-羰基二咪唑、2-氯-1,3-二甲基咪唑鎓氯化物或2-氯-1-甲基碘化吡啶的存在下的酰胺偶联来合成通式(IX)的化合物(参见Chemistry of Peptide Synthesis,Ed.N.Leo Benoiton,Taylor&Francis,2006,ISBN-10:1-57444-454-9)。聚合物结合的试剂,例如聚合物结合的二环己基碳二亚胺,也适合于这种偶联反应。该反应优选在0℃至80℃的温度范围内在适宜的溶剂例如二氯甲烷、四氢呋喃、乙腈、N,N-二甲基甲酰胺或乙酸乙酯中并在碱例如三乙胺、N,N-二异丙基乙胺或1,8-二氮杂双环[5.4.0]十一碳-7-烯的存在下进行(参见方案2)。对于T3P肽偶联条件,参见Organic Process Research&Development2009,13,900-906。通式(VII)和(VIII)的化合物是可商购的或可通过本领域技术人员已知的方法制备或可类似于本领域技术人员已知的方法制备。
在第二步(方案2)中,通式(IX)的化合物在偶联卤化物例如碘化铜(I)、溴化铜(I)或碱如甲醇钠或酸如甲磺酸的存在下环化,得到通式(II)的3-羟基吡唑。该反应优选在0℃至120℃的温度范围内在合适的溶剂如1,2-二氯乙烷、乙腈、N,N-二甲基甲酰胺、正丙醇、正丁醇或乙酸乙酯中进行。
或者,通式(II)的3-羟基吡唑也可例如由通式(X)的受保护的3-羟基吡唑制备(方案3)。这里的保护基团R优选为苄基基团或三烷基甲硅烷基基团。
R=保护基团
方案3
在方案3的第一步中,通过通式(X)的受保护的3-羟基吡唑与通式(XI)的吡嗪基卤在卤化铜例如碘化铜(I)的存在下的N-芳基化来制备通式(XII)的化合物。该反应优选在0℃至120℃的温度范围内在适宜的溶剂例如乙腈或N,N-二甲基甲酰胺中并在碱例如三乙胺或碳酸铯的存在下进行。通式(XII)的化合物可通过本领域技术人员已知的方法制备或可类似于本领域技术人员已知的方法制备(例如,Chem.Med.Chem.2015,10,1184-1199)。通式(XI)的化合物中的“X”基团优选为氯、溴或碘。
在第二步中,由通式(XII)的化合物制备通式(XIII)的5-碘代吡唑。该反应在强碱例如正丁基锂或二异丙基酰胺锂和碘的存在下进行。该反应优选在-78℃至-60℃的温度范围内在适宜的溶剂例如乙醚或四氢呋喃中进行。
式(XV)的化合物可例如通过在合适溶剂中的式(XIII)的化合物与化合物M-A(XIV)、在加入适宜量的过渡金属催化剂尤其是钯催化剂如二乙酸钯或双(三苯基膦)二氯化钯(II)或镍催化剂如乙酰丙酮镍(II)或双(三苯基膦)氯化镍(II)的情况下优选在升高的温度下在有机溶剂如1,2-二甲氧基乙烷中的反应制备。“M”基团代表例如B(ORb)(ORc),其中Rb和Rc基团独立地为例如氢或(C1-C4)-烷基,或者,如果基团Rb和Rc彼此键合,则它们一起为亚乙基或亚丙基。通过本领域技术人员熟知的标准方法对式(XV)的化合物脱保护,最终得到通式(II)的3-羟基吡唑,其可例如如方案1中所述进一步转化为本发明的化合物。
本发明的化合物也可例如通过下面方案4中所示的合成方法由通式(XVI)的取代的5-氨基-1-吡嗪基-1H-吡唑-3-醇制备。
方案4描述了通过本领域技术人员已知的方法或类似于本领域技术人员已知的方法通过其中Hal优选为溴或碘、更优选碘的通式(XIX)的化合物与化合物M-A(XX)、在加入适宜量的过渡金属催化剂尤其是钯催化剂如二乙酸钯或双(三苯基膦)二氯化钯(II)或镍催化剂如乙酰丙酮镍(II)或双(三苯基膦)氯化镍(II)的情况下优选在升高的温度下在有机溶剂如1,2-二甲氧基乙烷或二噁烷中的反应来合成式(Ia)的化合物。“M”基团代表例如Mg-Hal、Zn-Hal、Sn((C1-C4)-烷基)3、锂、铜或B(ORb)(ORc),其中Rb和Rc基团独立地为例如氢、(C1-C4)-烷基,或者,如果基团Rb和Rc彼此键合,则它们一起为亚乙基或亚丙基。
通式(XIX)的化合物可通过通式(XVIII)的5-氨基吡唑与惯用的有机和无机亚硝酸酯例如亚硝酸1,1-二甲基乙酯、亚硝酸叔丁酯或亚硝酸异戊酯在可用试剂例如溴/氯化铜(I)和铜(II)、碘或二碘甲烷的混合物存在下的重氮化和随后的Sandmeyer反应来制备(方案4)。该反应优选在0℃至120℃的温度范围内在适宜的溶剂例如二氯甲烷、乙腈或N,N-二甲基甲酰胺中进行。
通式(XVIII)的化合物通过本领域技术人员已知的方法或类似于本领域技术人员已知的方法通过通式(XVII)的取代吡唑与亲电试剂例如亲电卤化试剂如N-氯代琥珀酰亚胺(当R3=Cl时)、N-溴代琥珀酰亚胺(当R3=Br时)、N-碘代琥珀酰亚胺(当R3=I时)或亲电硝化试剂如硝化酸、四氟硼酸硝鎓、硝酸铵/三氟乙酸(当R3=NO2时)或亲电氟化试剂如DAST、Selectfluor、N-氟代苯磺酰亚胺(当R3=F时)的反应合成。该反应优选在0℃至120℃的温度范围内在适宜的溶剂例如N,N-二甲基甲酰胺、1,2-二氯乙烷或乙腈中进行。通式(XVIII;其中R3=CN)的化合物可例如通过在合适溶剂中的式(XVIII,其中R3=卤素,优选地R3=Br、I)的化合物与金属氰化物例如氰化锌、在加入适宜量的过渡金属催化剂尤其是钯催化剂如四(三苯基膦)钯(0)或二乙酸钯或双(三苯基膦)二氯化钯(II)或镍催化剂如乙酰丙酮镍(II)或双(三苯基膦)氯化镍(II)的情况下优选在升高的温度下在有机溶剂例如1,2-二甲氧基乙烷或N,N-二甲基甲酰胺中的反应制备。通常合适的交叉偶联方法有R.D.Larsen,Organometallics in Process Chemistry 2004Springer Verlag;I.Tsuji,Palladium Reagents and Catalysts 2004Wiley;和M.Belier,C.Bolm,TransitionMetals for Organic Synthesis 2004VCH-Wiley中描述的那些。其他合适的合成方法描述于Chem.Rev.2006,106,2651;Platinum Metals Review,2009,53,183;Platinum MetalsReview 2008,52,172;和Acc.Chem.Res.2008,41,1486中。
通式(XVII)的化合物的合成可通过通式(XVI)的取代的5-氨基-1-吡嗪基-1H-吡唑-3-醇与通式(III)的卤化物在碱的存在下通过本领域技术人员已知的方法或类似于本领域技术人员已知的方法的烷基化来进行(参见方案4)。碱可为碱金属(例如,锂、钠、钾或铯)的碳酸盐。该反应优选在室温至150℃的温度范围内在适宜的溶剂例如二氯甲烷、乙腈、N,N-二甲基甲酰胺或二碘甲烷中进行。通式(III)的化合物中的“X”基团优选为氯、溴或碘。通式(XVI)的化合物可商购获得或可通过本领域技术人员已知的方法制备或类似于本领域技术人员已知的方法制备,例如通过通式(VIII)的肼并吡嗪与氰基乙酸乙酯的反应制备(参见,例如,Synthetic Communications(2012),42(10),1401-1410)。
可使用上述通式(Ia)的化合物通过本领域技术人员熟知的标准方法制备其中R1a=H的通式(Ic)和其中R1=NR9R10的通式(Id)的本发明化合物。
方案5
如方案5中所示,通式(Ic)的酸可通过通式(Ia)的酯按照本领域技术人员已知的方法或类似于本领域技术人员已知的方法水解来制备。水解可在碱或路易斯酸的存在下进行。碱可为碱金属(例如,锂、钠或钾)的氢氧化物盐,并且水解反应优选在室温至120℃的温度范围内进行。
通式(Id)的本发明化合物经由例如通式(Ic)的酸与通式(XXI)的胺在酰胺偶联试剂例如丙烷膦酸酐(T3P)、二环己基碳二亚胺、N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺、N,N′-羰基二咪唑、2-氯-1,3-二甲基咪唑鎓氯化物或2-氯-1-甲基碘化吡啶的存在下的酰胺偶联来合成(参见Chemistry of Peptide Synthesis,Ed.N.Leo Benoiton,Taylor&Francis,2006,ISBN-10:1-57444-454-9)。聚合物结合的试剂,例如聚合物结合的二环己基碳二亚胺,也适合于这种偶联反应。该反应优选在0℃至80℃的温度范围内在合适的溶剂例如二氯甲烷、乙腈、N,N-二甲基甲酰胺或乙酸乙酯中并在碱例如三乙胺、N,N-二异丙基乙胺或1,8-二氮杂双环[5.4.0]十一碳-7-烯的存在下进行。对于T3P肽偶联条件,参见OrganicProcess Research&Development 2009,13,900-906。
式(I)的本发明化合物(和/或其盐),后文统称为“本发明的化合物”,对广谱的经济上重要的单子叶和双子叶一年生有害植物具有优异的除草功效。
因此,本发明还提供了一种防治不需要的植物或调节植物(优选在植物作物中)的生长的方法,其中向植物(例如有害植物如单子叶或双子叶杂草或不需要的作物植物)、种子(例如籽粒、种子或营养繁殖体如块茎或带芽的枝条部分)或其上生长植物的区域(例如耕种区域)施用一种或多种本发明的化合物。本发明的化合物可例如在播种前(视需要也可通过掺入到土壤中)、出苗前或出苗后应用。可由本发明的化合物防治的一些代表性单子叶和双子叶杂草植物群的具体实例如下,但该列举并不旨在对特定物种施加限制。
以下属的单子叶有害植物:山羊草属、冰草属、剪股颖属、看麦娘属、阿披拉草属、燕麦属、臂形草属、雀麦属、蒺藜草属、鸭跖草属、狗牙根属、莎草属、龙爪茅属、马唐属、稗属、荸荠属、穇属、画眉草属、野黍属、羊茅属、飘拂草属、异蕊花属、白茅属、鸭嘴草属、千金子属、黑麦草属、雨久花属、黍属、雀稗属、虉草属、梯牧草属、早熟禾属、筒轴茅属、慈姑属、藨草属、狗尾草属、高粱属。
以下属的双子叶杂草:苘麻属、苋属、豚草属、盘果苘属(Anoda)、春黄菊属、霓裳草属(Aphanes)、蒿属、滨藜属、雏菊属、鬼针草属、荠属、飞廉属、决明属、矢车菊属、黎属、蓟属、旋花属、曼陀罗属、山蚂蝗属、角刺酸模属、糖芥属、大戟属、鼬瓣花属、牛膝菊属、拉拉藤属、木槿属、番薯属、地肤属、野芝麻属、独荇菜属、母草属、母菊属、薄荷属、山靛属、粟米草属、勿忘草属、罂粟属、牵牛属、车前属、蓼属、马齿苋属、毛茛属、萝卜属、蔊菜属、节节菜属、酸模属、猪毛菜属、千里光属、田菁属、黄花稔属、百芥属、茄属、苦苣菜属、尖瓣花属、繁缕属、蒲公英属、菥蓂属、车轴草属、荨麻属、婆婆纳属、堇菜属、苍耳属。
当在萌芽前将本发明的化合物施用于土壤表面时,或者完全阻止杂草幼苗的出苗,或者杂草生长直至达到子叶阶段,但随后停止生长。
如果出苗后施用活性成分至植物的绿色部分,则生长在处理后停止,并且有害植物将停留在施用时的生长阶段,或在一定时间后完全死亡,因此以这种方式,对作物植物有害的杂草的竞争很早就并以持续的方式被消除。
本发明的化合物可在有用植物的作物中具有选择性,也可用作非选择性除草剂。
由于它们的除草和植物生长调节性质,活性成分也可用来防治已知或仍有待开发的遗传修饰植物的作物中的有害植物。通常,转基因植物以特定的有利性质为特征,例如特征在于对农用化学工业中使用的某些活性成分、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收成物的数量、质量、可储存性、组成和特定成分方面。例如,已知淀粉含量升高或淀粉质量改变的转基因植物,或者收成物中脂肪酸组成不同的那些。其他特定性质在于对非生物胁迫因素的耐受性或抗性,例如热、冷、干旱、盐度和紫外辐射。
优选在有用和观赏植物的经济上重要的转基因作物中使用式(I)的本发明化合物或其盐。
式(I)的化合物可用作有用植物的作物中的除草剂,所述作物对除草剂的植物毒性作用具有抵抗性或已通过基因工程使得其对除草剂的植物毒性作用具有抵抗性。
产生与现有植物相比具有改善性质的新植物的常规方法包括例如传统栽培方法和突变体的产生。或者,可借助于重组方法来产生具有改良性质的新植物(参见,例如,EP0221044、EP 0131624)。已描述例如以下几种情况:为了改良植物中合成的淀粉而对作物植物进行遗传改良(例如,WO 92/011376A、WO 92/014827A、WO 91/019806A);对某些草铵膦型(参考例如EP 0242236 A、EP 0242246 A)或草甘膦型(WO92/000377A)或磺酰脲型(EP0257993 A、US 5,013,659)的除草剂或通过“基因堆叠”而对这些除草剂的组合或混合物具有抗性的转基因作物植物,如转基因作物植物,例如商品名或名称为OptimumTM GATTM(草甘膦ALS耐受)的玉米或大豆,
-能够产生苏云金芽孢杆菌毒素(Bt毒素)的转基因作物植物,例如棉花,这种毒素使得植物抵抗特定害虫的侵害(EP 0142924 A、EP0193259A),
-具有改良的脂肪酸组成的转基因作物植物(WO 91/013972A),
-具有新成分或次生代谢物例如新的植物抗毒素的遗传修饰作物植物,这导致提高抗病性(EP 0309862 A、EP 0464461 A),
-光呼吸减少的遗传修饰植物,其具有更高的产量和更高的抗逆性(EP 0305398A),
-产生药学或诊断上重要的蛋白质的转基因作物植物(“分子农业医药”),
-具有更高产量或更好质量的转基因作物植物,
-以例如上述新性质的组合(“基因堆叠”)为特征的转基因作物植物。
可用于产生具有改良性质的新型转基因植物的许多分子生物学技术原则上是已知的;参见例如I.Potrykus和G.Spangenberg(eds)Gene Transfer to Plants,SpringerLab Manual(1995),Springer Verlag Berlin,Heidelberg或Christou,"Trends in PlantScience"1(1996)423-431)。
对于这样的遗传操作,可将允许通过DNA序列的重组进行诱变或序列改变的核酸分子引入到质粒中。借助标准方法,可以例如进行碱基交换、去除部分序列或添加天然或合成序列。为了将DNA片段彼此连接起来,可以向片段添加接头或连接子;例如参见Sambrook等人,1989,Molecular Cloning,A Laboratory Manual,2nd ed.,Cold Spring HarborLaboratory Press,Cold Spring Harbor,NY;或Winnacker"Gene und Klone”[Genes andClones],VCH Weinheim,第二版,1996。
例如,可通过表达至少一种相应的反义RNA,用于实现共抑制作用的有义RNA,或通过表达至少一种特异性切割上述基因产物的转录物的适当构建的核酶,来产生具有降低的基因产物活性的植物细胞。为此,首先可以使用涵盖基因产物的整个编码序列(包括可能存在的任何侧翼序列)的DNA分子,以及仅涵盖编码序列的部分的DNA分子,在该情况下这些部分必须足够长以在细胞中具有反义效应。也可以使用与基因产物的编码序列具有高度同源性但不与其完全相同的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期望的区室中。然而,为了实现在特定区室中的定位,可以例如将编码区与将确保在特定区室中定位的DNA序列连接。这样的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;Wolter等人,Proc.Natl.Acad.Sci.USA 85(1988),846-850;Sonnewald等人,Plant J.1(1991),95-106)。核酸分子也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的技术再生以产生完整的植物。原则上,转基因植物可以是任何期望的植物物种的植物,即不仅可以是单子叶植物,而且可以是双子叶植物。以这种方式可获得性质通过同源(=天然)基因或基因序列的过表达、压制或抑制或者异源(=外源)基因或基因序列的表达而改变的转基因植物。
本发明的化合物(I)可优选用于对生长调节剂(例如2,4-D、麦草畏)或者对抑制必需植物酶(例如乙酰乳酸合酶(ALS)、EPSP合酶、谷氨酰胺合酶(GS)或羟基苯基丙酮酸双加氧酶(HPPD))的除草剂或者对来自磺酰脲类、草甘膦类、草铵膦类或苯甲酰异噁唑类及类似活性成分的除草剂或者对这些活性成分的任何期望的组合具有抗性的转基因作物中。
本发明的化合物可特别优选用于对草甘膦和草铵膦、草甘膦和磺酰脲或咪唑啉酮的组合具有抗性的转基因作物植物中。最优选地,本发明的化合物可用于转基因作物植物如商品名或名称为例如OptimumTM GATTM(草甘膦ALS耐受)的玉米或大豆中。
当在转基因作物中使用本发明的活性成分时,不仅发生在其他作物中观察到的对有害植物的作用,而且还经常在特定的转基因作物中发生应用特定的效应,例如可防治的杂草的改变或明确地扩宽的范围,对于应用可使用的改变的施用率,优选与转基因作物具有抗性的除草剂良好地结合,以及影响转基因作物植物的生长和产量。
本发明因此还涉及本发明的式(I)的化合物作为除草剂在转基因作物植物中防治有害植物的用途。
本发明的化合物可以可湿性粉剂、可乳化浓缩物、可喷雾溶液、喷粉产品或颗粒的形式在惯用制剂中施用。本发明因此还提供了包含本发明的化合物的除草和植物生长调节组合物。
本发明的化合物可根据需要的生物学和/或物理化学参数以各种方式配制。可能的制剂包括例如:可湿性粉剂(WP)、水溶性粉剂(SP)、水溶性浓缩物、可乳化浓缩物(EC)、乳液(EW)如水包油和油包水乳液、可喷雾溶液、悬浮浓缩物(SC)、基于油或水的分散体、油混溶性溶液、胶囊混悬剂(CS)、喷粉产品(DP)、敷料、用于撒播和土壤施用的颗粒、微粒形式的颗粒(GR)、喷雾颗粒、吸收和吸附颗粒、水分散性颗粒(WG)、水溶性颗粒(SG)、ULV制剂、微胶囊和蜡。这些单个制剂类型原则上是已知的并在下述文献中有描述:Winnacker-Küchler,"Chemische Technologie”[Chemical Technology],Volume 7,C.Hanser Verlag Munich,第四版,1986,Wade van Valkenburg,"Pesticide Formulations",Marcel Dekker,N.Y.,1973,K.Martens,"Spray Drying"Handbook,第三版,1979,G.Goodwin Ltd.London。
必要的配制助剂(如惰性材料、表面活性剂、溶剂和其他添加剂)同样是已知的并描述于例如:Watkins,"Handbook of Insecticide Dust Diluents and Carriers",第二版,Darland Books,Caldwell N.J.,H.v.Olphen,"Introduction to Clay ColloidChemistry",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",MCPubl.Corp.,Ridgewood N.J.,Sisley和Wood,"Encyclopedia of Surface ActiveAgents",Chem.Publ.Co.Inc.,N.Y.1964, [Interface-active Ethylene Oxide Adducts],Wiss.Verlagsgesell.,Stuttgart 1976,"ChemischeTechnologie",volume 7,C.Hanser Verlag Munich,第四版,1986中。
在这些制剂的基础上,也可以与其他活性成分(例如杀虫剂、杀螨剂、除草剂、杀真菌剂)组合,并也可与安全剂、肥料和/或生长调节剂组合,例如成品配制物的形式或作为桶混合物。
混合制剂中或桶混物中可用于本发明的化合物的组合伴体是例如基于抑制例如乙酰乳酸合酶、乙酰辅酶A羧化酶、纤维素合酶、烯醇丙酮莽草酸-3-磷酸合酶、谷氨酰胺合成酶、对羟基苯基丙酮酸双加氧酶、八氢番茄红素去饱和酶、光系统I、光系统II或原卟啉原氧化酶的已知活性成分,如从例如Weed Research 26(1986)441-445或“The PesticideManual”,第16版,The British Crop Protection Council and the Royal Soc.ofChemistry,2006及其中引用的文献已知的。可与本发明的化合物组合的已知除草剂或植物生长调节剂为例如以下,其中所述活性成分根据国际标准化组织(ISO)以其“通用名称”或以化学名称或以代码编号提及。它们总是涵盖所有使用形式,例如酸、盐、酯以及所有异构形式如立体异构体和旋光异构体,即使它们没有被明确提及。
这样的除草混合伴体的实例有:
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)、枯草多(alloxydim-sodium)、莠灭净(ametryn)、氨唑草酮(amicarbazone)、酰胺氯(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)、氯氨吡啶酸二甲基铵盐(aminopyralid-dimethylammonium)、aminopyralid-tripromine、杀草强(amitrol)、氨基磺酸铵、莎稗磷(anilofos)、磺草灵(asulam)、磺草灵-钾(asulam-potassium)、磺草灵-钠(asulam-sodium)、莠去津(atrazin)、唑啶草酮(azafenidin)、四唑嘧磺隆(azimsulfuron)、氟丁酰草胺(beflubutamid)、(S)-(-)-氟丁酰草胺、精氟丁酰草胺(beflubutamid-M)、草除灵(benazolin)、高特克(benazolin-ethyl)、草除灵-二甲基铵(benazolin-dimethylammonium)、草除灵-钾(benazolin-potassium)、乙丁氟灵(benfluralin)、呋草黄(benfuresat)、苄嘧磺隆(bensulfuron)、免速隆(bensulfuron-methyl)、地散磷(bensulid)、灭草松(bentazon)、灭草松-钠(bentazon-sodium)、双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、bicyclopyron、甲羧除草醚(bifenox)、双丙氨膦(bilanafos)、双丙氨膦钠(bilanafos-sodium)、bipyrazon、双草醚(bispyribac)、双草醚钠(bispyribac-sodium)、二氯异噁草松(bixlozon)、除草定(bromacil)、除草定-锂(bromacil-lithium)、除草定-钠(bromacil-sodium)、溴丁酰草胺(bromobutid)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴苯腈丁酸酯(bromoxynil-butyrate)、溴苯腈钾(bromoxynil-potassium)、溴苯腈庚酸酯(bromoxynil-heptanoate)和溴苯腈辛酸酯(bromoxynil-octanoate)、羟草酮(busoxinon)、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(butylat)、唑草胺(cafenstrol)、克草胺酯(cambendichlor)、双酰草胺(carbetamid)、氟唑草酮(carfentrazon)、氟酮唑草(carfentrazon-ethyl)、草灭畏(chloramben)、草灭畏-铵(chloramben-ammonium)、草灭畏-二醇胺(chloramben-diolamine)、草灭畏-甲基(chlroamben-methyl)、草灭畏-甲基铵(chloramben-methylammonium)、草灭畏-钠(chloramben-sodium)、氯溴隆(chlorbromuron)、伐草克(chlorfenac)、伐草克-铵(chlorfenac-ammonium)、伐草克钠(chlorfenac-sodium)、燕麦酯(chlorfenprop)、chlorfenprop-methyl、氯甲丹(chlorflurenol)、整形醇(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆酸(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、chlorophthalim、绿麦隆(chlorotoluron)、氯磺隆(chlorsulfuron)、敌草索(chlorthal)、氯酞酸二甲酯(chlorthal-dimethyl)、吲哚酮草酸(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)、异恶草松(clomazone)、氯甲酰草胺(clomeprop)、二氯吡啶酸(clopyralid)、二氯吡啶酸甲酯(clopyralid-methyl)、二氯吡啶酸乙醇胺盐(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)、氨基氰(cyanamid)、氰草津(cyanazin)、环草敌(cycloat)、cyclopyranil、cyclopyrimorat、环丙嘧磺隆(cyclosulfamuron)、噻草酮(cycloxydim)、氰氟草酸(cyhalofop)、氰氟草酯(cyhalofop-butyl)、环丙津(cyprazin)、2,4-D(包括其-铵、-丁氧基乙酯(-butotyl)、-丁基酯、-胆碱、-二乙基铵、-二甲基铵、-二醇胺、-doboxyl、-十二烷基铵、-etexyl、-乙基酯、-2-乙基己基酯、-庚基铵、-异丁基酯、-异辛基酯、-异丙基酯、-异丙基铵、-锂、-meptyl、-甲基酯、-钾、-十四烷基铵、-三乙基铵、-三异丙醇铵、-tripromine和-三乙醇胺(-trolamine)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(dalapon-calcium)、茅草枯-镁(dalapon-Magnesium)、茅草枯-钠(dalapon-sodium)、棉隆(dazomet)、棉隆-钠(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,麦草畏-biproamine、麦草畏-N,N-双(3-氨基丙基)甲胺、麦草畏-丁氧基乙酯(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-二乙醇胺铵盐(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-乙醇胺(dicamba-olamine)、麦草畏-钾(dicamba-potassium)、麦草畏-钠(dicamba-sodium)、麦草畏-三乙醇胺(dicamba-triethanolamine))、敌草腈(dichlobenil)、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-滴丙酸丁氧基乙酯(dichlorprop-butotyl)、2,4-滴丙酸-二甲基铵(dichlorprop-dimethylammonium)、dichlorprop-etexyl、2,4-滴丙酸-乙基铵(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(dichlorprop-potassium)、2,4-滴丙酸-钠(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(dichlorprop-P-potassium)、2,4-滴丙酸-钠(dichlorprop-sodium)、禾草灵(diclofop)、二氯硫醚磷(diclofop-methyl)、精禾草灵(diclofop-P)、精禾草灵(diclofop-p-methyl)、双氯磺草胺(diclosulam)、乙酰野燕枯(difenzoquat)、野燕枯柳酸甲酯(difenzoquat-metilsulfate)、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)、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)、二溴杀草快(diquat-dibromid)、敌草快二氯盐(diquat-dichloride)、氟硫草定(dithiopyr)、敌草隆(diuron)、DNOC、DNOC-铵、DNOC-钾、DNOC-钠、茵多酸(endothal)、茵多酸-二铵、茵多酸-二钾、茵多酸-二钠、epyrifenacil(S-3100)、ePTC、戊草丹(esprocarb)、乙丁烯氟灵(ethalfluralin)、胺苯磺隆(ethametsulfuron)、胺苯黄隆(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、噁唑禾草灵(fenoxaprop)、精噁唑禾草灵(fenoxaprop-P)、噁唑禾草灵(fenoxaprop-ethyl)、高噁唑禾草灵(fenoxaprop-p-ethyl)、芬诺杀磺隆(fenoxasulfone)、苯唑氟草酮(fenpyrazone)、fenquinotrione、四唑酰草胺(fentrazamid)、氟燕灵(flamprop)、氟燕灵异丙酯(flamprop-isoproyl)、氟燕灵甲酯(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、甲氟燕灵(flamprop-M-methyl)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氯氟吡啶酸(florpyrauxifen)、氯氟吡啶酯(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(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、氯乙氟灵(fluchloralin)、氟噻草胺(flufenacet)、氟哒嗪草酸(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac)、氟烯草酸酯(flumiclorac-pentyl)、丙炔氟草胺(flumioxazin)、氟草隆(fluometuron)、9-羟基笏甲酸(flurenol)、芴丁酯(flurenol-butyl)、芴二甲基铵(flurenol-dimethylammonium)、芴甲酯(flurenol-methyl)、乙羧氟草醚(fluoroglycofen)、(fluoroglycofen-ethyl)、flupropanat、flupropanat-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(fluridon)、氟咯草酮(flurochloridon)、氯氟吡氧乙酸(fluroxypyr)、氯氟吡氧乙酸丁氧基丙酯(fluroxypyr-butometyl)、氯氟吡氧乙酸异辛酯(fluroxypyr-meptyl)、呋草酮(flurtamon)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟磺草胺(fomesafen-sodium)、甲酰氨磺隆(foramsulfuron)、甲酰氨基嘧磺隆(foramsulfuron-sodium)、杀木膦(fosamine)、膦铵素(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)、草甘膦二铵(glyphosate-diammonium)、草甘膦二甲基铵(glyphosate-dimethylammonium)、草甘膦钾(glyphosate-potassium)、草甘膦钠(glyphosate-sodium)、草甘膦倍半钠(glyphosate-sesquisodium)和草甘膦三甲基硫盐(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、halauxifen、halauxifen-methyl、氟硝磺酰胺(halosafen)、氯吡嘧磺隆(halosulfuron)、吓草硫甲(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(haloxifop-sodium)、环嗪酮(hexazinon)、HNPC-A8169,即丙-2-炔-1-基(2S)-2-{3-[(5-叔丁基吡啶-2-基)氧基]苯氧基}丙酸酯、HW-02,即1-(二甲氧基磷酰基)乙基(2,4-二氯苯氧基)乙酸酯、hydantocidin、咪草酸(imazamethabenz)、咪草酯(imazamethabenz-methyl)、甲氧咪草烟(imazamox)、甲氧咪草烟酸铵(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)、灭草喹甲酯(imazaquin-methyl)、咪唑乙烟酸(imazethapyr)、咪唑乙烟酸铵(imazethapyr-ammonium)、唑吡嘧磺隆(imazosulfuron)、茚草酮(indanofan)、indaziflam、碘甲磺隆(iodosulfuron)、碘甲磺隆甲酯(iodosulfuron-methyl)、碘甲磺隆甲酯钠盐(iodosulfuron-methyl-sodium)、碘苯腈辛酸(ioxynil)、碘苯腈辛酸锂(ioxynil-lithium)、碘苯腈辛酸(ioxynil-octanoate)、碘苯腈辛酸钾(ioxynil-potassium)和碘苯腈辛酸钠(ioxynil-sodium)、三唑酰草胺(ipfencarbazone)、异丙隆(isoproturon)、异恶隆(isouron)、异恶酰草胺(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)、环草定(lenacil)、利谷隆(linuron)、MCPA、MCPA-丁氧基乙酯(MCPA-butotyl)、MCPA-丁酯、MCPA-二甲基铵、MCPA-二醇胺、MCPA-2-乙基己酯、MCPA-乙酯、MCPA-异丁酯、MCPA-异辛酯、MCPA-异丙酯、MCPA-异丙基铵、MCPA-甲酯、MCPA-醇胺、MCPA-钾、MCPA-钠和MCPA-三乙醇胺、MCPB、MCPB-甲酯、MCPB-乙酯和MCPB-钠、2-甲-4-氯丙酸(mecoprop)、2-甲-4-氯丙酸丁氧基乙酯(mecoprop-butotyl)、2-甲-4-氯丙酸二甲基铵(mecoprop-dimethylammonium)、2-甲-4-氯丙酸二醇胺(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)和精2-甲-4-氯丙酸钾(mecoprop-P-potassium)、苯噻酰草胺(mefenacet)、氯磺酰草胺(mefluidid)、氯磺酰草胺-二醇胺(mefluidid-diolamine)、氯磺酰草胺-钾(mefluidid-potassium)、甲磺胺磺隆(mesosulfuron)、甲磺胺磺隆甲酯(mesosulfuron-methyl)、甲磺胺磺隆-钠(mesosulfuron-sodium)、甲基磺草酮(mesotrion)、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)、metazosulfuron、甲基苯噻隆(methabenzthiazuron)、methiopyrsulfuron、methiozolin、甲基异硫氰酸盐(methyl isothiocyanat)、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)、甲黄隆(metsulfuron-methyl)、草达灭(molinat)、绿谷隆(monolinuron)、单嘧磺隆(monosulfuron)、单嘧磺隆甲酯(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-苄基氧基吡唑、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(nonanoic acid(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)、丙炔恶草酮(oxadiargyl)、恶草酮(oxadiazon)、环氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、乙氧氟草醚(oxyfluorfen)、百草枯(paraquat)、百草枯二氯盐(paraquat dichloride)、百草枯二甲基硫酸盐(paraquat-dimethylsulfate)、克草猛(pebulate)、二甲戊灵(pendimethalin)、五氟磺草胺(penoxsulam)、五氯苯酚、环戊恶草酮(pentoxazone)、烯草胺(pethoxamid)、石油、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)、恶草酸(propaquizafop)、扑灭津(propazine)、苯胺灵(propham)、异丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、磺唑苯甲酸(propoxycarbazone-sodium)、丙嗪嘧磺隆(propyrisulfuron)、炔苯酰草胺(propyzamid)、苄草丹(prosulfocarb)、氟磺隆(prosulfuron)、双唑草腈(pyraclonil)、吡草醚(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、磺酰草吡唑(pyrasulfotol)、吡唑特(pyrazolynat(pyrazolat))、吡嘧磺隆(母酸)(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、苄草唑(pyrazoxyfen)、丙酯草醚(pyribambenz)、异丙酯草醚(pyribambenz-isopropyl)、丙酯草醚(pyribambenz-propyl)、嘧啶肟草醚(pyribenzoxim)、稗草丹(pyributicarb)、3-苯基-4-羟基-6-氯哒嗪(pyridafol)、哒草特(pyridat)、环酯草醚(pyriftalid)、嘧草醚(pyriminobac)、甲基嘧草醚(pyriminobac-methyl)、pyrimisulfan、嘧草硫醚(pyrithiobac)、(pyrithiobac-sodium)、砜吡草唑(pyroxasulfon)、甲氧磺草胺(pyroxsulam)、二氯喹啉酸(quinclorac)、二氯喹啉酸二甲基铵(quinclorac-dimethylammonium)、二氯喹啉酸甲酯(quinclorac-methyl)、氯甲喹啉酸(quinmerac)、灭藻醌(quinoclamin)、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)、QYM-201,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)、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)、嘧磺隆酸(sulfometuron)、甲嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、SYN-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)及其盐(例如,TCA-铵、TCA-钙、TCA乙酯、TCA-镁、TCA-钠)、丁噻隆(tebuthiuron)、tefuryltrione、环磺酮(tembotrion)、吡喃草酮(tepraloxydim)、特草定(terbacil)、特草灵(terbucarb)、甲氧去草净(terbumeton)、特丁津(terbuthylazin)、特丁净(terbutryn)、tetflupyrolimet、thaxtomin、噻吩草胺(thenylchlor)、噻唑烟酸(thiazopyr)、噻吩卡巴腙(thiencarbazone)、噻吩卡巴腙-甲基(thiencarbazone-methyl)、噻吩磺隆(thifensulfuron,thifensulfuron-methyl)、禾草丹(thiobencarb)、tiafenacil、tolpyralat、topramezon、三甲苯草酮(tralkoxydim)、氟酮磺草胺(triafamon)、野燕畏(tri-allate)、醚苯磺隆(triasulfuron)、三嗪氟草胺(triaziflam)、苯磺隆(tribenuron)、苯黄隆(tribenuron-methyl)、三氯吡氧乙酸(triclopyr)、三氯吡氧乙酸丁氧基乙酯(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)、三甲隆三氟甲磺隆(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-氯-2-[3-(二氟甲基)异噁唑-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-甲酸氰甲酯、丙-2-炔-1-基4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸酯、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。
作为可能的混合伴体的植物生长调节剂的实例有:
脱落酸、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-aminolevulinic acid)、醇草啶(ancymidol)、6-苄基氨基嘌呤(6-benzylaminopurine)、芸苔素内酯(brassinolide)、乙基芸苔素内酯(brassinolide-ethyl)、儿茶酚(catechin)、壳寡糖(CO;CO与LCO的不同在于它们不具有侧脂肪酸链,侧脂肪酸链是LCO所特有的。CO,有时也称为N-乙酰基壳寡糖,同样由GlcNAc基团组成,但具有将它们与几丁质分子[(C8H13NO5)n,CAS编号1398-61-4]和壳聚糖分子[(C5H11NO4)n,CAS编号9012-76-4]区分开来的侧链装饰)、几丁质化合物、矮壮素(chlormequat chloride)、调果酸(cloprop)、环丙酰草胺(cyclanilide)、3-(环丙-1-烯基)丙酸、丁酰肼(daminozide)、棉隆(dazomet)、棉隆-钠(dazomet-sodium)、正癸醇、敌草克(dikegulac)、调呋酸(dikegulac-sodium)、茵多酸(endothal)、茵多酸二钾(endothal-dipotassium)、茵多酸二钠(endothal-disodium)和茵多酸单(N,N-二甲基烷基铵)、乙烯利(ethephon)、氟节胺(flumetralin)、抑草丁(flurenol)、抑草丁丁酯(flurenol-butyl)、抑草丁甲酯(flurenol-methyl)、呋嘧醇(flurprimidol)、氯吡脲(forchlorfenuron)、赤霉素(gibberellic acid)、抗倒胺(inabenfid)、吲哚-3-乙酸(IAA)、4-吲哚-3-基丁酸、稻瘟灵(isoprothiolane)、噻菌灵(probenazole)、茉莉酸(jasmonic acid)、茉莉酸或其衍生物(例如,茉莉酸甲酯)。脂质壳寡糖(LCO,有时也称为共生结瘤(Nod)信号(或Nod因子)或称为Myc因子)由βl,4-连接的N-乙酰基-D-葡糖胺("GlcNAc")基团的寡糖骨架组成,该基团具有在非还原端缩合的N-连接的脂肪酰基链。如本领域技术人员所知,LCO在其骨架中GlcNAc基团的数量、其长度和脂肪酰基链的饱和度以及还原和非还原糖部分的取代方面不同)、亚油酸或其衍生物、亚麻酸或其衍生物、马来酰肼、助壮素氯化物(mepiquat chloride)、助壮素五硼酸盐(mepiquat pentaborate)、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、4-氧代-4[(2-苯乙基)氨基]丁酸、多效唑(paclobutrazole)、4-苯基丁酸、N-苯基酞氨酸、调环酸(prohexadione)、调环酸钙(prohexadione-calcium)、茉莉酮(prohydrojasmone)、水杨酸、水杨酸甲酯、独脚金内酯(strigolactone)、四氯硝基苯(tecnazene)、噻苯隆(thidiazuron)、三十烷醇(triacontanol)、抗倒酯(trinexapac)、(trinexapac-ethyl)、tsitodef、烯效唑(uniconazole)、烯效唑-P(uniconazole-P)、2-氟-N-(3-甲氧基苯基)-9H-嘌呤-6-胺。
可与式(I)的本发明化合物组合并任选地与其他活性成分(如上文所列的杀虫剂、杀螨剂、除草剂、杀真菌剂)组合使用的安全剂优选选自:
S1)式(S1)的化合物
其中符号和指数如下定义:
nA为0至5、优选0至3的自然数;
RA 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
WA为未取代或被取代的二价杂环基团,其选自具有1至3个环杂原子的部分不饱和或芳族五元杂环,所述环杂原子选自N和O,其中环中存在至少一个氮原子和至多一个氧原子,优选选自(WA 1)至(WA 4)的基团,
mA为0或1;
RA 2为ORA 3、SRA 3或NRA 3RA 4或者具有至少一个氮原子和至多3个杂原子(优选选自O和S)的饱和或不饱和3-至7-元杂环,其经由氮原子与(S1)中的羰基基团连接并且未被取代或被选自(C1-C4)-烷基、(C1-C4)-烷氧基或任选被取代的苯基的基团所取代,优选式ORA 3、NHRA 4或N(CH3)2的基团,尤其是式ORA 3的基团;
RA 3为氢或者未取代或被取代的脂族烃基团,优选具有总共1至18个碳原子;
RA 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或者被取代或未取代的苯基;
RA 5为H、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C8)-烷基、氰基或COORA 9,其中RA 9为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-羟烷基、(C3-C12)-环烷基或三-(C1-C4)-烷基甲硅烷基;
RA 6、RA 7、RA 8相同或不同并为氢、(C1-C8)-烷基、(C1-C8)-卤代烷基、(C3-C12)-环烷基或者被取代或未取代的苯基;
优选地:
a)二氯苯基吡唑啉-3-甲酸类型的化合物(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”)和如WO-A-91/07874中所描述的相关化合物;
b)二氯苯基吡唑甲酸的衍生物(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)和如EP-A-333 131和EP-A-269 806中所描述的相关化合物;
c)1,5-二苯基吡唑-3-甲酸的衍生物(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)和如例如EP-A-268 554中所描述的相关化合物;
d)三唑甲酸类型的化合物(S1d),优选化合物如解草唑(-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)和如EP-A-174 562和EP-A-346 620中所描述的相关化合物;
e)5-苄基-或5-苯基-2-异噁唑啉-3-甲酸或5,5-二苯基-2-异噁唑啉-3-甲酸类型的化合物(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)和如WO-A-91/08202中所描述的相关化合物,或5,5-二苯基-2-异噁唑啉-3-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")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中所描述。
S2)式(S2)的喹啉衍生物
其中符号和指数如下定义:
RA 1为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、硝基或(C1-C4)-卤代烷基;
nB为0至5、优选0至3的自然数;
RB 2为ORB 3、SRB 3或NRB 3RB 4或者具有至少一个氮原子和至多3个杂原子(优选选自O和S)的饱和或不饱和3-至7-元杂环,其经由氮原子与(S2)中的羰基基团连接并且未被取代或被选自(C1-C4)-烷基、(C1-C4)-烷氧基或任选被取代的苯基的基团所取代,优选式ORB 3、NHRB 4或N(CH3)2的基团,尤其是式ORB 3的基团;
RB 3为氢或者未取代或被取代的脂族烃基团,优选具有总共1至18个碳原子;
RB 4为氢、(C1-C6)-烷基、(C1-C6)-烷氧基或者被取代或未取代的苯基;
TB为(C1或C2)-链烷二基链,其未被取代或者被一个或两个(C1-C4)-烷基基团或被[(C1-C3)-烷氧基]羰基所取代;
优选地:
a)8-喹啉氧基乙酸类型的化合物(S2a),优选地
(5-氯-8-喹啉氧基)乙酸1-甲基己酯("解毒喹")(S2-1)、
(1,3-二甲基丁-1-基)(5-氯-8-喹啉氧基)乙酸酯(S2-2)、
(5-氯-8-喹啉氧基)乙酸4-烯丙氧基丁酯(S2-3)、
1-烯丙氧基丙-2-基(5-氯-8-喹啉氧基)乙酸酯(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-亚丙基亚胺氧基)-1-乙酯(S2-8)、2-氧代丙-1-基(5-氯-8-喹啉氧基)乙酸酯(S2-9)和相关化合物,如EP-A-86 750、EP-A-94 349和EP-A-191736或EP-A-0 492 366中所描述的,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中所描述的;
b)(5-氯-8-喹啉氧基)丙二酸类型的化合物(S2b),优选地化合物如(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)丙二酸甲基乙基酯和相关化合物,如EP-A-0 582 198中所描述的。
S3)式(S3)的化合物
其中符号和指数如下定义:
RC 1为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C2-C4)-烯基、(C2-C4)-卤代烯基、(C3-C7)-环烷基,优选二氯甲基;
RC 2、RC 3相同或不同并为氢、(C1-C4)烷基、(C2-C4)烯基、(C2-C4)炔基、(C1-C4)卤代烷基、(C2-C4)卤代烯基、(C1-C4)烷基氨基甲酰基-(C1-C4)烷基、(C2-C4)烯基氨基甲酰基-(C1-C4)烷基、(C1-C4)烷氧基-(C1-C4)烷基、二氧戊环基-(C1-C4)烷基、噻唑基、呋喃基、呋喃基烷基、噻吩基、哌啶基、取代或未取代的苯基,或者RC 2和RC 3一起形成被取代或未取代的杂环环,优选噁唑烷、噻唑烷、哌啶、吗啉、六氢嘧啶或苯并噁嗪环;
优选地:
二氯乙酰胺类型的活性成分,其通常用作出苗前安全剂(作用于土壤的安全剂),例如
“二氯丙烯胺”(N,N-二烯丙基-2,2-二氯乙酰胺)(S3-1)、
来自Stauffer的"R-29148"(3-二氯乙酰基-2,2,5-三甲基-1,3-噁唑烷)(S3-2)、
来自Stauffer的"R-28725"(3-二氯乙酰基-2,2-二甲基-1,3-噁唑烷)(S3-3)、
"benoxacor"(4-二氯乙酰基-3,4-二氢-3-甲基-2H-1,4-苯并噁嗪)(S3-4)、
来自PPG Industries的"PPG-1292"(N-烯丙基-N-[(1,3-二氧杂环戊烷-2-基)甲基]二氯乙酰胺)(S3-5)、
来自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)、
来自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)、
来自TRI-Chemical RT的"TI-35"(1-二氯乙酰基氮杂环庚烷)(S3-8)、
"diclonon"(dicyclonon)或"BAS145138"或"LAB145138"(S3-9)、
来自BASF的((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)、
"解草恶唑(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)式(S4)的N-酰基磺酰胺及其盐,
其中符号和指数如下定义:
AD为SO2-NRD 3-CO或CO-NRD 3-SO2
XD为CH或N;
RD 1为CO-NRD 5RD 6或NHCO-RD 7;
RD 2为卤素、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、硝基、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
RD 3为氢、(C1-C4)-烷基、(C2-C4)-烯基或(C2-C4)-炔基;
RD 4为卤素、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、(C3-C6)-环烷基、苯基、(C1-C4)-烷氧基、氰基、(C1-C4)-烷硫基、(C1-C4)-烷基亚磺酰基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基或(C1-C4)-烷基羰基;
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、苯基或含有vD个选自氮、氧和硫的杂原子的3-至6-元杂环基,其中后七个基团被vD个选自卤素、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C2)-烷基亚磺酰基、(C1-C2)-烷基磺酰基、(C3-C6)-环烷基、(C1-C4)-烷氧基羰基、(C1-C4)-烷基羰基和苯基及在环状基团的情况下,也选自(C1-C4)-烷基和(C1-C4)-卤代烷基的取代基所取代;
RD 6为氢、(C1-C6)-烷基、(C2-C6)-烯基或(C2-C6)-炔基,其中后三个基团被vD个选自卤素、羟基、(C1-C4)-烷基、(C1-C4)-烷氧基和(C1-C4)-烷硫基的基团所取代,或
RD 5和RD 6与携带它们的氮原子一起形成吡咯烷基或哌啶基基团;
RD 7为氢、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、(C1-C6)-烷基、(C3-C6)-环烷基,其中后2个基团被vD个选自卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基及在环状基团的情况下,也选自(C1-C4)-烷基和(C1-C4)-卤代烷基的取代基所取代;
nD为0、1或2;
mD为1或2;
vD为0、1、2或3;
在这些中,优选N-酰基磺酰胺类型的化合物,例如下式(S4a)的化合物,其例如从WO-A-97/45016已知
其中:
RD 7为(C1-C6)-烷基、(C3-C6)-环烷基,其中后2个基团被vD个选自卤素、(C1-C4)-烷氧基、(C1-C6)-卤代烷氧基和(C1-C4)-烷硫基及在环状基团的情况下,也选自(C1-C4)-烷基和(C1-C4)-卤代烷基的取代基所取代;
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3;
mD为1或2;
vD为0、1、2或3;
以及
酰基磺酰氨基苯甲酰胺,例如下式(S4b)的,其例如从WO-A-99/16744已知,
例如以下的那些:其中
RD 5=环丙基而(RD 4)=2-OMe("环丙磺酰胺(cyprosulfamide)",S4-1),
RD 5=环丙基而(RD 4)=5-Cl-2-OMe(S4-2),
RD 5=乙基而(RD 4)=2-OMe(S4-3),
RD 5=异丙基而(RD 4)=5-Cl-2-OMe(S4-4),和
RD 5=异丙基而(RD 4)=2-OMe(S4-5)
以及
式(S4c)的N-酰基氨磺酰苯基脲类型的化合物,其例如从EP-A-365484已知,
其中:
RD 8和RD 9独立地为氢、(C1-C8)-烷基、(C3-C8)-环烷基、(C3-C6)-烯基、(C3-C6)-炔基,
RD 4为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、CF3,
mD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,
以及
式(S4d)的N-苯基磺酰对苯二甲酰胺,其例如从CN 101838227已知,
例如以下的那些: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)来自羟基芳族化合物和芳族-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中所描述的。
S6)来自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中所描述的。
S7)式(S7)的化合物,如WO-A-1998/38856中所描述的,
其中符号和指数如下定义:
RE 1、RE 2独立地为卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷基、(C1-C4)-烷基氨基、二-(C1-C4)-烷基氨基、硝基;
AE为COORE 3或COSRE 4
RE 3、RE 4独立地为氢、(C1-C4)-烷基、(C2-C6)-烯基、(C2-C4)-炔基、氰基烷基、(C1-C4)-卤代烷基、苯基、硝基苯基、苄基、卤代苄基、吡啶基烷基和烷基铵,
nE 1为0或1
nE 2、nE 3独立地为0、1或2,
优选地:
二苯基甲氧基乙酸,
二苯基甲氧基乙酸乙酯,
二苯基甲氧基乙酸甲酯(CAS登录号41858-19-9)(S7-1)。
S8)式(S8)的化合物,如WO-A-98/27049中所描述的,
其中:
XF为CH或N,
nF在XF=N的情况下为0至4的整数并在XF=CH的情况下为0至5的整数,
RF 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、硝基、(C1-C4)-烷硫基、(C1-C4)-烷基磺酰基、(C1-C4)-烷氧基羰基、任选被取代的苯基、任选被取代的苯氧基,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳基团中的每一个未被取代或者被一个或多个、优选至多三个选自卤素和烷氧基的相同或不同基团所取代;或其盐,
优选以下的化合物:其中
XF为CH,
nF为0至2的整数,
RF 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,
RF 2为氢或(C1-C4)-烷基,
RF 3为氢、(C1-C8)-烷基、(C2-C4)-烯基、(C2-C4)-炔基或芳基,其中上述含碳基团中的每一个未被取代或者被一个或多个、优选至多三个选自卤素和烷氧基的相同或不同基团所取代,
或其盐。
S9)来自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登录号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登录号95855-00-8),如WO-A-1999/000020中所描述的。
S10)式(S10a)或(S10b)的化合物
如WO-A-2007/023719和WO-A-2007/023764中所描述的
其中:
RG 1为卤素、(C1-C4)-烷基、甲氧基、硝基、氰基、CF3、OCF3,
YG、ZG彼此独立地代表O或S,
nG为0至4的整数,
RG 2为(C1-C16)-烷基、(C2-C6)-烯基、(C3-C6)-环烷基、芳基;苄基、卤代苄基,
RG 3为氢或(C1-C6)-烷基。
S11)已知作为拌种剂的氧基亚氨基化合物类型的活性成分(S11),例如
"解草腈(oxabetrinil)"((Z)-1,3-二氧杂环戊烷-2-基甲氧基亚氨基(苯基)乙腈)(S11-1),其已知作为拌种安全剂用于小米/高粱来抵抗异丙甲草胺的损害,
"氟草肟(fluxofenim)"(1-(4-氯苯基)-2,2,2-三氟-1-乙酮O-(1,3-二氧杂环戊烷-2-基甲基)肟)(S11-2),其已知作为拌种安全剂用于小米/高粱来抵抗异丙甲草胺的损害,和
"解草胺腈(cyometrinil)"或"CGA-43089"((Z)-氰基甲氧基亚氨基(苯基)乙腈)(S11-3),其已知作为拌种安全剂用于小米/高粱来抵抗异丙甲草胺的损害。
S12)来自异硫代苯并二氢吡喃酮类的活性成分(S12),例如[(3-氧代-1H-2-苯并噻喃-4(3H)-亚基)甲氧基]乙酸甲酯(CAS登录号205121-04-6)(S12-1)和来自WO-A-1998/13361的相关化合物。
S13)来自组(S13)的一种或多种化合物:
"萘二甲酸酐(naphthalic anhydride)"(1,8-萘二甲酸酐)(S13-1),其已知作为拌种安全剂用于玉米来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),其已知作为安全剂用于播种稻(sown rice)来抵抗丙草胺(pretilachlor),
"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用于小米/高粱来抵抗甲草胺(alachlor)和异丙甲草胺(metolachlor)的损害,
"CL 304415"(CAS登录号31541-57-8)
来自American Cyanamid的(4-羧基-3,4-二氢-2H-1-苯并吡喃-4-乙酸)(S13-4),其已知作为安全剂用于玉米来抵抗咪唑啉酮类(imidazolinones)的损害,
来自Nitrokemia的"MG 191"(CAS登录号96420-72-3)(2-二氯甲基-2-甲基-1,3-二氧杂环戊烷)(S13-5),其已知作为安全剂用于玉米,
"MG 838"(CAS登录号133993-74-5)
来自Nitrokemia的(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)"(O,O-二乙基-S-2-乙基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"(4-氯苯基甲基氨基甲酸酯)(S13-9)。
S14)除了对有害植物的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"(S-1-甲基1-苯基乙基哌啶-1-硫代甲酸酯),其已知作为安全剂用于稻来抵抗除草剂禾草敌(molinate)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),其已知作为安全剂用于稻来抵抗除草剂吡嘧磺隆(imazosulfuron)的损害,
"苄草隆(cumyluron)"="JC 940"(3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲,参见JP-A-60087254),其已知作为安全剂用于稻来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),其已知作为安全剂用于稻来抵抗一些除草剂的损害,
来自Kumiai的“CSB"(1-溴-4-(氯甲基磺酰基)苯)(CAS登录号54091-06-4),已知其在稻中作为安全剂来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中所描述的,其中
RH 1为(C1-C6)-卤代烷基基团,
RH 2为氢或卤素,
RH 3、RH 4独立地为氢、(C1-C16)-烷基、(C2-C16)-烯基或(C2-C16)-炔基,
其中后3个基团中的每一个未被取代或者被一个或多个选自卤素、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、未取代或被取代的(C3-C6)-环烷基、未取代或被取代的苯基和未取代或被取代的杂环基的基团所取代,
或(C3-C6)-环烷基、(C4-C6)-环烯基、在环的一侧上稠合到4至6-元饱和或不饱和碳环的(C3-C6)-环烷基或在环的一侧上稠合到4至6-元饱和或不饱和碳环的(C4-C6)-环烯基,
其中后4个基团中的每一个未被取代或者被一个或多个选自卤素、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、未取代或被取代的(C3-C6)-环烷基、未取代或被取代的苯基和未取代或被取代的杂环基的基团所取代,
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与直接连接的氮原子一起代表四至八元杂环,除氮原子外,其也可含有进一步的环杂原子,优选地至多两个选自N、O和S的进一步的环杂原子,并且其未被取代或者被一个或多个选自卤素、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)-烷硫基的基团所取代。
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(dicamba))、
3,6-二氯-2-甲氧基苯甲酸1-(乙氧基羰基)乙酯(lactidichlor-ethyl)。
特别优选的安全剂为吡唑解草酯(mefenpyr-diethyl)、环丙磺酰胺(cyprosulfamide)、双苯噁唑酸(isoxadifen-ethyl)、解毒喹(cloquintocet-mexyl)、烯丙酰草胺(dichlormid)和metcamifen。
可湿性粉剂为可均匀分散在水中的制剂,在活性成分外,并且在除稀释剂或惰性物质之外,还包含离子型和/或非离子型的表面活性剂(润湿剂、分散剂),例如聚乙氧基化烷基酚、聚乙氧基化脂肪醇、聚乙氧基化脂肪胺、脂肪醇聚二醇醚硫酸盐、链烷磺酸盐、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。为了产生可湿性粉剂,将活性除草成分细细研磨,例如在惯用装置如锤磨机、鼓风磨机和喷气磨机中,并同时或随后与配制助剂混合。
可乳化浓缩物通过将活性成分溶解在有机溶剂(例如丁醇、环己酮、二甲基甲酰胺、二甲苯)或相对高沸点的芳烃或烃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)来制备。可使用的乳化剂的实例有:烷基芳基磺酸钙盐,如十二烷基苯磺酸钙,或非离子乳化剂如脂肪酸聚二醇酯、烷基芳基聚二醇醚、脂肪醇聚二醇醚、环氧丙烷/环氧乙烷缩合产物、烷基聚醚、失水山梨醇酯例如失水山梨醇脂肪酸酯、或聚氧乙烯失水山梨醇脂例如聚氧乙烯失水山梨醇脂肪酸酯。
喷粉产品通过将活性成分与精细分布的固体(例如滑石,天然粘土如高岭土、膨润土和叶蜡石,或硅藻土)一起研磨获得。
悬浮浓缩物可以是基于水的或基于油的。它们可例如通过借助于商业珠磨机湿磨并任选地添加如已在上文(例如针对其他配制物类型)列出的表面活性剂来产生。
乳液,例如水包油乳液(EW),可例如借助于搅拌器、胶体磨和/或静态混合器使用水性有机溶剂和任选地如已在上文(例如针对其他配制物类型)列出的表面活性剂来产生。
颗粒剂可通过将活性成分喷洒到能够吸附的颗粒状惰性材料上或通过借助于粘合剂(例如聚乙烯醇、聚丙烯酸钠或矿物油)向载体物质(如砂、高岭土或颗粒状惰性材料)的表面施加活性成分浓缩物来制备。合适的活性成分也可以生产肥料颗粒的惯用方式造粒——如果需要作为与肥料的混合物的话。
水分散性颗粒通常通过惯用方法如喷雾干燥、流化床造粒、盘式造粒、用高速混合器混合和挤出来生产而不用固体惰性材料。
对于盘式颗粒、流化床颗粒、挤出机颗粒和喷雾颗粒的生产,参见例如"Spray-Drying Handbook"第三版,1979,G.Goodwin Ltd.,London,J.E.Browning,"Agglomeration",Chemical and Engineering 1967,147页ff.;"Perry's ChemicalEngineer's Handbook",第五版,McGraw-Hill,New York 1973,pp.8-57中的过程。
关于作物保护组合物的制剂的更多细节,参见例如G.C.Klingman,"Weed Controlas a Science",John Wiley and Sons,Inc.,New York,1961,81-96页和J.D.Freyer,S.A.Evans,"Weed Control Handbook",第五版,Blackwell Scientific Publications,Oxford,1968,101-103页。
农用化学制剂通常含有0.1重量%至99重量%、尤其是0.1重量%至95重量%的本发明化合物。在可湿性粉末中,活性成分浓度为例如约10重量%至90重量%,至100重量%的其余部分由惯用的制剂成分组成。在可乳化浓缩物中,活性成分浓度可为约1重量%至90重量%,并且优选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、优选通常5重量%至20重量%的活性成分;可喷雾溶液含有约0.05重量%至80重量%、优选2重量%至50重量%的活性成分。在水分散性颗粒的情况下,活性成分含量部分地取决于活性成分是呈液体还是固体形式以及所使用的造粒助剂、填料等。在水分散性颗粒中,活性成分的含量例如在1重量%至95重量%之间,优选在10重量%至80重量%之间。
另外,所提及的活性成分制剂任选地包含相应的惯用粘着剂(sticker)、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、蒸发抑制剂及影响pH和粘度的试剂。
以这些制剂为基础,还可以产生与其他杀虫活性物质(例如杀昆虫剂、杀螨剂、除草剂、杀真菌剂)的组合,以及与安全剂、肥料和/或生长调节剂的组合,例如以成品制剂的形式或作为桶混合物。
对于施用,视需要以惯用的方式稀释市售形式的制剂,例如在可湿性粉剂、可乳化浓缩物、分散体和水分散性颗粒的情况下用水稀释。粉剂形式的制剂、用于土壤施用的颗粒剂或用于散播的颗粒剂和可喷雾溶液在施用前通常不用其他惰性物质进一步稀释。
式(I)的化合物及其盐的所需施用量随外部条件如尤其是温度、湿度和所用除草剂的类型而变化。其可在宽的限度内变化,例如0.001至10.0kg/ha或更多的活性物质,但优选0.005至5kg/ha,更优选0.01至1.5kg/ha的范围内,更优选0.05至1kg/ha。这既适用于出苗前的施用也适用于出苗后的施用。
载体是天然或合成的有机或无机物质,活性成分与其混合或组合以获得更好的适用性,特别是对于向植物或植物部分或种子的施用。载体(其可以是固体或液体)通常是惰性的,并应适合用于农业中。
可用的固体或液体载体包括:例如铵盐和天然岩粉,如高岭土、粘土、滑石、白垩、石英、凹凸棒土、蒙脱石或硅藻土,以及合成岩粉,如细碎的二氧化硅、氧化铝和天然或合成硅酸盐、树脂、蜡、固体肥料、水、醇类(尤其是丁醇)、有机溶剂、矿物油和植物油,及其衍生物。同样可以使用这样的载体的混合物。颗粒的可用固体载体包括:例如经粉碎并分级的天然岩石如方解石、大理石、浮石、海泡石、白云石、无机和有机面粉的合成颗粒,以及有机材料如锯末、椰子壳、玉米穗轴和烟草茎的颗粒。
合适的液化气体增量剂或载体为在标准温度和大气压下为气态的液体,例如气溶胶推进剂如卤代烃抑或丁烷、丙烷、氮气和二氧化碳。
在制剂中,可以使用增粘剂如羧甲基纤维素,呈粉末、颗粒或胶乳形式的天然和合成聚合物如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,抑或天然磷脂如脑磷脂和卵磷脂,以及合成磷脂。其他添加剂可为矿物油和植物油。
当使用的增量剂为水时,还可以使用例如有机溶剂作为辅助溶剂。可用的液体溶剂主要为:芳族化合物如二甲苯、甲苯或烷基萘,氯化芳族化合物或氯化脂族烃如氯苯、氯乙烯或二氯甲烷,脂族烃如环己烷,或石蜡如矿物油馏分,矿物油和植物油,醇类如丁醇或二醇及其醚和酯,酮类如丙酮、甲基乙基酮、甲基异丁基酮或环己酮,强极性溶剂如二甲基甲酰胺和二甲亚砜,以及水。
本发明的组合物还可包含其他组分,例如表面活性剂。可用的表面活性剂为具有离子或非离子性质的乳化剂和/或泡沫形成剂、分散剂或润湿剂,或这些表面活性剂的混合物。其实例是聚丙烯酸的盐、木质素磺酸的盐、苯酚磺酸或萘磺酸的盐、环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺的缩聚物、取代酚(优选烷基酚或芳基酚)、磺基琥珀酸酯的盐、牛磺酸衍生物(优选烷基牛磺酸盐)、聚乙氧基化醇或酚的磷酸酯、多元醇的脂肪酸酯及含有硫酸根、磺酸根和磷酸根的化合物的衍生物,例如烷基芳基聚二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、蛋白质水解物、木质素亚硫酸盐废液和甲基纤维素。如果活性成分之一和/或惰性载体之一不溶于水和当在水中实现施用时,表面活性剂的存在是必要的。表面活性剂的比例为本发明组合物的5至40重量%之间。可以使用染料如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,有机染料如茜素染料、偶氮染料和金属酞菁染料,及微量营养素如铁、锰、硼、铜、钴、钼和锌的盐。
如果适宜,还可以存在其他附加组分,例如保护性胶体、粘结剂、粘合剂、增稠剂、触变物质、渗透剂、稳定剂、螯合剂、络合剂。通常,活性成分可与任何常用于配制目的的固体或液体添加剂组合。通常,本发明的组合物和制剂含有0.05重量%至99重量%、0.01重量%至98重量%、优选0.1重量%至95重量%、更优选0.5重量%至90重量%的活性成分,最优选10重量%至70重量%。本发明的活性成分或组合物可原样使用,或者根据它们各自的物理和/或化学性质以其配制物的形式或由其制备的使用形式使用,如气溶胶、胶囊悬浮剂、冷雾化浓缩物、温热雾化浓缩物、包封颗粒剂、细颗粒剂、用于种子处理的可流动浓缩物、即用型溶液、粉剂、可乳化浓缩物、水包油乳液、油包水乳液、大颗粒剂、微颗粒剂、油分散性粉末、油混溶性可流动浓缩物、油混溶性液体、泡沫、糊剂、农药包衣种子、悬浮浓缩物、悬浮乳液浓缩物、可溶性浓缩物、悬浮液、可喷射粉末、可溶性粉末、粉剂和颗粒剂、水溶性颗粒剂或片剂、用于种子处理的水溶性粉末、可湿性粉剂、浸有活性成分的天然产物和合成物质、及在聚合物物质中和在种子包衣材料中的微包封以及此外ULV冷雾化和温热雾化制剂。
提及的制剂可以本身已知的方式产生,例如通过将活性成分与至少一种惯用增量剂、溶剂或稀释剂、乳化剂、分散剂和/或粘结剂或固定剂、润湿剂、防水剂、任选地干燥剂和UV稳定剂及任选地染料和颜料、消泡剂、防腐剂、辅助增稠剂、增粘剂、赤霉素和其他加工助剂混合。
本发明的组合物不仅包括已准备好使用并可用合适的装置应用到植物或种子上的制剂,而且包括必须在使用前用水稀释的市售浓缩物。
本发明的活性成分可原样存在或以其(商业标准)制剂存在,或以从这些配制物制备的使用形式作为与其他(已知)活性成分如杀昆虫剂、引诱剂、止繁殖剂、杀细菌剂、杀螨剂、杀线虫剂、杀真菌剂、生长调节剂、除草剂、肥料、安全剂或信息化学物质的混合物存在。
用活性成分或组合物对植物和植物部分的本发明处理直接进行或通过用惯用处理方法对其周围环境、栖息地或储存空间的作用进行,例如通过浸渍、喷洒、喷雾、灌溉、蒸发、撒粉、雾化、撒播、起泡、喷涂、铺展、浇水(湿透)、滴灌以及在繁殖材料的情况下、尤其是在种子的情况下,还通过干式种子处理、湿式种子处理、浆液处理、覆皮、包以一层或多层包衣等。也可以通过超低容量方法应用活性成分或者注射活性成分制剂或活性成分自身到土壤中。
也如下所述,用本发明的活性成分或组合物处理转基因种子具有特别重要的意义。这涉及到含有至少一种使得能够表达具有杀虫性质的多肽或蛋白质的异源基因的植物种子。转基因种子中的异源基因可源自例如芽孢杆菌属、根瘤菌属、假单胞菌属、沙雷氏菌属、木霉属、棒形杆菌属、球囊霉属或粘帚霉属物种的微生物。该异源基因优选源自芽孢杆菌属物种,在此情况下,基因产物对欧洲玉米螟和/或西方玉米根虫有效。异源基因更优选源自苏云金芽孢杆菌。
在本发明的上下文中,本发明的组合物单独或以合适的制剂施用于种子。优选地,在足够稳定以在处理过程中不会发生损害的状态下处理种子。通常,种子可在收获和播种之间的任何时间处理。惯常使用从植物分离并去除了穗轴、壳、茎、皮、毛或果肉的种子。例如,可以使用已经收获、清洁和干燥至水分含量低于15重量%的种子。或者,也可以使用在干燥后例如已用水处理并然后再次干燥的种子。
通常,在处理种子时,必须确保选择施用于种子的本发明组合物和/或其他添加剂的量使得不削弱种子的萌芽并且不损害由其长出的植物。特别是在活性成分在某些施用量下可能表现出植物毒性效应的情况下,必须确保这一点。
本发明的组合物可直接施用,即不含任何其他组分且不经稀释。通常,优选将组合物以合适的制剂的形式施用于种子。用于种子处理的合适制剂和方法是本领域技术人员已知的并描述于例如以下文件中:US4,272,417A、US 4,245,432 A、US 4,808,430、US 5,876,739、US2003/0176428A1、WO 2002/080675 A1、WO 2002/028186 A2。
本发明的活性成分可转化为惯用的拌种制剂,如溶液、乳液、悬浮液、粉末、泡沫、浆液或其他种子包衣组合物及ULV制剂。
这些制剂以已知的方式通过将活性成分与惯用添加剂例如惯用增量剂和溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、辅助增稠剂、粘合剂、赤霉素及水混合而产生。
可存在于根据本发明可用的拌种制剂中的染料为所有惯用于这些目的的染料。可以使用微溶于水的颜料或可溶于水的染料。实例包括名称为罗丹明B、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于根据本发明可用的拌种制剂中的可用润湿剂为所有促进润湿且惯用于农用化学活性成分的配制的物质。可优选使用烷基萘磺酸盐,如二异丙基或二异丁基萘磺酸盐。
可存在于根据本发明可用的拌种制剂中的合适的分散剂和/或乳化剂为所有惯用于农用化学活性成分的配制的非离子、阴离子和阳离子分散剂。可优选使用非离子或阴离子分散剂或者非离子或阴离子分散剂的混合物。合适的非离子分散剂尤其包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚二醇醚和三苯乙烯基苯酚聚二醇醚及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其是木质素磺酸盐、聚丙烯酸盐和芳基磺酸盐-甲醛缩合物。
可存在于根据本发明可用的拌种制剂中的消泡剂为所有惯用于农用化学活性成分的配制的泡沫抑制物质。可优选使用有机硅消泡剂和硬脂酸镁。
可存在于根据本发明可用的拌种制剂中的防腐剂为所有在农用化学组合物中可用于此类目的的物质。实例包括双氯酚和苯甲醇半缩甲醛。
可存在于根据本发明可用的拌种制剂中的辅助增稠剂为所有在农用化学组合物中可用于此类目的的物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土和细碎二氧化硅。
可存在于根据本发明可用的拌种制剂中的可用粘着剂为所有可用于拌种产品中的惯用粘结剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和羟乙基纤维素(tylose)。
根据本发明可用的拌种制剂可直接使用或可在已预先用水稀释后使用以处理广泛不同的种子,其包括转基因植物的种子。在此情况下,与通过表达形成的物质的相互作用也可能发生额外的协同效应。
为了用根据本发明可用的拌种制剂或用通过加水而由其制备的制剂处理种子,可用的设备为所有习惯上可用于拌种的混合单元。具体而言,拌种程序为将种子放入到混合器中,加入特定所需量的拌种制剂(原样或在先用水稀释后),并混合它们直至制剂均匀分布在种子上。如果适宜,之后进行干燥操作。
本发明的活性成分(具有良好的植物相容性、有利的恒温动物毒性和良好的环境相容性)适合于保护植物和植物器官、增加收获量和改善收获作物的品质。它们可优选用作作物保护剂。它们对通常敏感和具有抗性的物种及此外对所有或特定的发育阶段都具有活性。
可根据本发明处理的植物包括以下主要作物植物:玉米、大豆、棉花、芸苔属油料种子如欧洲油菜(例如,加拿大油菜)、芜菁、芥菜型油菜(例如,(野)芥菜)和埃塞俄比亚芥(Brassica carinata)、水稻、小麦、甜菜、甘蔗、燕麦、黑麦、大麦、小米和高粱、黑小麦、亚麻、葡萄以及来自各种植物类群的各种果实和蔬菜,例如蔷薇科(Rosaceae sp.)(例如,仁果类水果如苹果和梨,还有核果如杏、樱桃、杏仁和桃子,以及浆果如草莓)、茶蔗子科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceae sp.)、漆树科(Anacardiaceae sp.)、山毛榉科(Fagaceae sp.)、桑科(Moraceae sp.)、木犀科(Oleaceaesp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如,香蕉树和种植园)、茜草科(Rubiaceae sp.)(例如,咖啡)、山茶科(Theaceae sp.)、梧桐科(Sterculiceaesp.)、芸香科(Rutaceae sp.)(例如,柠檬、橙子和葡萄柚);茄科(Solanaceaesp.)(例如,西红柿、马铃薯、胡椒、茄子)、百合科(Liliaceae sp.)、菊科(Compositae sp.)(例如,莴苣、朝鲜蓟和菊苣–包括根菊苣(root chicory)、苦苣(endive)或普通菊苣(common chicory))、伞形科(Umbelliferae sp.)(例如,胡萝卜、欧芹、旱芹和块根芹)、葫芦科(Cucurbitaceae sp.)(例如,黄瓜–包括小黄瓜(gherkins)、南瓜、西瓜、葫芦和甜瓜)、葱科(Alliaceaesp.)(例如,韭菜和洋葱)、十字花科(Cruciferae sp.)(例如,白球甘蓝、红球甘蓝、花茎甘蓝、花椰菜、抱子甘蓝、青菜、球茎甘蓝、萝卜、辣根、水芹和大白菜)、豆科(Leguminosae sp.)(例如,花生、豌豆和扁豆–例如菜豆和蚕豆)、黎科(Chenopodiaceae sp.)(例如,唐莴苣、饲料甜菜、菠菜、甜菜根)、锦葵科(Malvaceae)(例如,秋葵)、天门冬科(Asparagaceae)(例如,天门冬);园林和森林中的有用植物和观赏植物;和在每种情况下这些植物的遗传改良类型。
如上文所提到的,可以根据本发明处理所有植物及其部分。在一个优选的实施方案中,处理野生植物物种和植物栽培品种,或通过常规生物育种技术如杂交或原生质体融合获得的那些及其部分。在进一步优选的实施方案中,处理通过基因工程方法——如果适宜,与常规方法结合——获得的转基因植物和植物栽培品种(遗传改良生物体)及其部分。上文已解释了术语“部分”或“植物的部分”或“植物部分”。根据本发明,特别优选处理相应的商业上惯用的植物栽培品种的植物或那些使用中的植物。植物栽培品种应理解为指通过常规育种、通过诱变或通过重组DNA技术培育出的具有新性质(“性状”)的植物。它们可以是栽培品种、变种、生物型和基因型。
本发明的处理方法可用于处理遗传改良生物体(GMO),例如,植物或种子。遗传改良植物(或转基因植物)为其中异源基因已被稳定地整合到基因组中的植物。术语“异源基因”基本上指的是植物外提供或组装的基因,并且其在引入到核基因组、叶绿体基因组或线粒体基因组中后赋予转化植物新的或改善的农艺性状或其他性状,因为它表达植物中存在的感兴趣的蛋白质或多肽或其他基因,或植物中存在的其他基因被下调或关闭(例如,借助反义技术、共抑制技术或RNAi技术[RNA干扰])。位于基因组中的异源基因也称为转基因。由其在植物基因组中的特定存在定义的转基因被称为转化或转基因事件。
取决于植物物种或植物栽培品种、它们的位置和生长条件(土壤、气候、生长期、养分(diet)),本发明的处理也可能产生超加性(“协同”)效应。例如,超出实际预期效果的以下效果是可能的:降低可根据本发明使用的活性成分和组合物的施用量和/或扩展活性谱和/或提高功效、更好的植物生长、增加对高温或低温的耐受性、增加对干旱或水或土壤盐分的耐受性、提高开花性能、更容易收获、加速成熟、更高的收获量、更大的果实、更高的株高、更绿的叶子颜色、更早开花、收获产品更高的质量和/或更高的营养价值、果实内更高的糖浓度、收获产品的更好储存稳定性和/或可加工性。
优选根据本发明处理的植物和植物栽培品种包括具有赋予这些植物特别有利的有用性状的遗传材料的所有植物(无论是通过育种还是生物技术手段或两者获得的)。
抗线虫植物的实例描述于例如以下美国专利申请中:11/765,491、11/765,494、10/926,819、10/782,020、12/032,479、10/783,417、10/782,096、11/657,964、12/192,904、11/396,808、12/166,253、12/166,239、12/166,124、12/166,209、11/762,886、12/364,335、11/763,947、12/252,453、12/209,354、12/491,396和12/497,221。
可根据本发明处理的植物为已经表现出杂种优势或杂交效应的特征的杂交植物,其通常导致更高的产量、活力、更好的健康以及对生物和非生物胁迫因素的抗性。这样的植物通常通过将自交雄性不育亲本系(雌性杂交亲本)与另一自交雄性可育亲本系(雄性杂交亲本)杂交而产生。杂交种子通常从雄性不育植物收获并出售给种植者。雄性不育植物有时(例如,在玉米中)可通过去雄(即机械去除雄性生殖器官或雄花)产生,但更典型的是,雄性不育是植物基因组中遗传决定子的结果。在该情况下,且尤其是当种子是待从杂交植物收获的所需产品时,确保含有导致雄性不育的遗传决定子的杂交植物中的雄性育性完全恢复通常是有益的。这可通过确保雄性杂交亲本具有适宜的育性恢复基因来实现,这些基因能够在含有导致雄性不育的遗传决定子的杂交植物中恢复雄性育性。雄性不育的遗传决定子可能位于细胞质中。例如,描述了芸苔属物种的胞质雄性不育(CMS)的实例。然而,雄性不育的遗传决定子也可位于核基因组中。雄性不育植物也可通过植物生物技术方法如基因工程获得。WO89/10396中描述了一种特别有用的获得雄性不育植物的方法,其中例如在雄蕊的绒毡层细胞中选择性表达核糖核酸酶如芽孢杆菌RNA酶。然后可通过在绒毡层细胞中表达核糖核酸酶抑制剂如芽孢杆菌RNA酶抑制剂(barstar)来恢复育性。
可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)为除草剂耐受性植物,即使得对一种或多种给定除草剂具有耐受性的植物。这样的植物可通过遗传转化或通过选择含有赋予这样的除草剂耐受性的突变的植物获得。
除草剂耐受性植物是例如草甘膦耐受性植物,即使得对除草剂草甘膦或其盐具有耐受性的植物。可通过多种方法使得植物对草甘膦具有耐受性。因此,例如,可通过用编码5-烯醇丙酮莽草酸-3-磷酸合酶(EPSPS)的基因转化植物来获得草甘膦耐受性植物。这样的EPSPS基因的实例是细菌鼠伤寒沙门氏菌的AroA基因(突变体CT7)(Comai等人,1983,Science,221,370-371)、土壤杆菌属的CP4基因(Barry等人,1992,Curr.Topics PlantPhysiol.7,139-145)、编码矮牵牛EPSPS的基因(Shah等人,1986,Science 233,478-481)、编码西红柿EPSPS的基因(Gasser等人,1988,J.Biol.Chem.263,4280-4289)或编码穇属(Eleusine)EPSPS的基因(WO01/66704)。它也可以是突变的EPSPS。也可通过表达编码草甘膦氧化还原酶的基因来获得草甘膦耐受性植物。也可通过表达编码草甘膦乙酰转移酶的基因来获得草甘膦耐受性植物。也可通过选择含有上述基因的天然存在突变的植物来获得草甘膦耐受性植物。表达赋予草甘膦耐受性的EPSPS基因的植物已有描述。表达赋予草甘膦耐受性的其他基因例如脱羧酶基因的植物已有描述。
其他除草剂抗性植物是例如使得对抑制谷氨酰胺合酶的除草剂(如双丙氨磷、草丁膦或草铵膦)具有耐受性的植物。这样的植物可通过表达使除草剂解毒的酶或对抑制具有抗性的谷氨酰胺合酶的突变体来获得。这样的有效的解毒酶的一个实例为编码草丁膦乙酰转移酶的酶(如来自链霉菌属物种的bar或pat蛋白)。表达外源草丁膦乙酰转移酶的植物已有描述。
其它的除草剂耐受性植物也为已使得对抑制羟苯基丙酮酸二加氧酶(HPPD)的除草剂具有耐受性的植物。羟苯基丙酮酸二加氧酶为催化对羟基苯基丙酮酸(HPP)转化为尿黑酸的反应的酶。可用编码天然存在的抗性HPPD酶的基因或编码突变或嵌合HPPD酶的基因转化对HPPD抑制剂具有耐受性的植物,如WO 96/38567、WO 99/24585、WO 99/24586、WO2009/144079、WO 2002/046387或US 6,768,044中所描述的。也可通过用编码某些酶的基因转化植物来获得对HPPD抑制剂的耐受性,这些酶使得能够形成尿黑酸,尽管HPPD抑制剂抑制天然HPPD酶。这样的植物描述于WO 99/34008和WO 02/36787中。除了编码HPPD耐受性酶的基因外,还可通过用编码预苯酸脱氢酶的基因转化植物来提高植物对HPPD抑制剂的耐受性,如WO 2004/024928中所描述。另外,通过向其基因组中插入编码代谢或降解HPPD抑制剂的酶例如CYP450酶的基因,可使得植物对HPPD抑制剂更具耐受性(参见WO 2007/103567和WO 2008/150473)。
其他除草剂抗性植物是已赋予对乙酰乳酸合酶(ALS)抑制剂的耐受性的植物。已知的ALS抑制剂包括例如磺酰脲、咪唑啉酮、三唑并嘧啶、嘧啶氧基(硫代)苯甲酸酯和/或磺酰氨基羰基三唑啉酮除草剂。已知ALS酶(也称为乙酰羟酸合酶,AHAS)中的不同突变赋予对不同除草剂和除草剂组的耐受性,如例如Tranel和Wright(Weed Science 2002,50,700-712)中所描述的。磺酰脲耐受性植物和咪唑啉酮耐受性植物的产生已有描述。也已描述其他磺酰脲耐受性和咪唑啉酮耐受性植物。
可通过诱导的诱变、通过在除草剂的存在下在细胞培养物中选择或通过突变育种来获得对咪唑啉酮和/或磺酰脲类具有耐受性的其他植物(例如,对于大豆,参见US 5,084,082,对于水稻,参见WO 97/41218,对于甜菜,参见US 5,773,702和WO 99/057965,对于莴苣,参见US5,198,599,或对于向日葵,参见WO 01/065922)。
也可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)对非生物胁迫因素具有耐受性。这样的植物可通过遗传转化或通过选择含有赋予这样的胁迫抗性的突变的植物获得。特别有用的胁迫耐受性植物包括以下:
a.含有能够降低植物细胞或植物中聚(ADP-核糖)聚合酶(PARP)基因的表达和/或活性的转基因的植物;
b.含有能够降低植物或植物细胞的PARG编码基因的表达和/或活性的胁迫耐受性增强转基因的植物;
c.含有胁迫耐受性增强转基因的植物,该转基因编码烟酰胺腺嘌呤二核苷酸补救生物合成途径的植物功能酶,包括烟酰胺酶、烟酸磷酸核糖基转移酶、烟酸单核苷酸腺苷酰转移酶、烟酰胺腺嘌呤二核苷酸合成酶或烟酰胺磷酸核糖基转移酶。
也可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)显示出收获产品数量、质量和/或储存稳定性的改变和/或收获产品特定组分的性质的改变,例如:
1)合成改性淀粉的转基因植物,与野生型植物细胞或植物中的合成淀粉相比,该改性淀粉在其物理化学特性、特别是直链淀粉含量或直链淀粉/支链淀粉比率、支化度、平均链长、侧链分布、粘度性能、胶凝强度、淀粉颗粒尺寸和/或淀粉颗粒形态方面发生了变化,使得该改性淀粉更适合于特定的应用。
2)合成非淀粉碳水化合物聚合物或合成与未经遗传修饰的野生型植物相比具有改变的性质的非淀粉碳水化合物聚合物的转基因植物。实例是产生多聚果糖(尤其是菊粉和果聚糖类型)的植物、产生α-1,4-葡聚糖的植物、产生α-1,6-支化α-1,4-葡聚糖的植物和产生交替糖的植物。
3)产生透明质酸的转基因植物。
4)转基因植物或杂交植物,如具有特定性质的洋葱,如“高可溶性固形物含量”、“低刺激性”(LP)和/或“长期储存”(LS)。
也可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)为具有改变的纤维特性的植物,如棉花植物。这样的植物可通过遗传转化或通过选择含有赋予这样的改变的纤维特性的突变的植物获得并包括:
a)含有改变的形式的纤维素合酶基因的植物,如棉花植物;
b)含有改变形式的rsw2或rsw3同源核酸的植物,如棉花植物,如蔗糖磷酸合酶的表达增加的棉花植物;
c)蔗糖合酶的表达增加的植物,如棉花植物;
d)植物,如棉花植物,其中在纤维细胞基础上的胞间连丝(plasmodesmatal)门控时间被改变,例如通过下调纤维选择性β-1,3-葡聚糖酶;
e)植物,如棉花植物,其纤维具有改变的反应性,例如通过表达N-乙酰氨基葡萄糖转移酶基因(包括nodC)和几丁质合酶基因。
也可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)为具有改变的油分布特征的植物,如油菜或相关的芸苔属植物。这样的植物可通过遗传转化或通过选择含有赋予这样的改变的油特征的突变的植物获得,并包括:
a)产生具有高油酸含量的油的植物,如油菜植物;
b)产生具有低亚麻酸含量的油的植物,如油菜植物;
c)产生具有低的饱和脂肪酸水平的油的植物,如油菜植物。
也可根据本发明处理的植物或植物栽培品种(其可通过植物生物技术方法如基因工程获得)为病毒抗性、例如对马铃薯病毒Y具有病毒抗性(阿根廷Tecnoplant的SY230和SY233事件)的植物如马铃薯,或对病害如马铃薯晚疫病(例如,RB基因)具有抗性的植物,或表现出降低的冷致甜度(其带有基因Nt-Inh、II-INV)的植物,或表现出矮化表型(A-20氧化酶基因)的植物。
也可根据本发明处理的植物或植物栽培品种(通过植物生物技术方法如基因工程获得)为具有改变的种子落粒性特征的植物,如油菜或相关的芸苔属植物。这样的植物可通过遗传转化或通过选择含有赋予这样的改变的特性的突变的植物获得并包括具有延迟或减少的种子落粒的植物如油菜。
可根据本发明处理的特别有用的转基因植物为具有转化事件或转化事件的组合的植物,它们是向美国农业部(USDA)美国动植物卫生检验署(APHIS)申请在美国的非管制状态已获批或未决的对象。与此相关的信息可随时从APHIS(4700River Road Riverdale,MD 20737,USA)获得,例如经由网站http://www.aphis.usda.gov/brs/not_reg.html。在本申请的提交日,具有以下信息的请求已在APHIS获批或未决:
-请求:请求的识别号。转化事件的技术描述可在APHIS网站上通过请求编号获得的具体请求文件中找到。这些描述在此通过引用公开。
-请求的扩展:指要求扩大范围或期限的先前请求。
-机构:提交请求的人的姓名。
-管制品:所讨论的植物物种。
-转基因表型:由转化事件赋予植物的性状。
-转化事件或线路:对其要求非管制状态的事件(有时也称为线路)的名称。
-APHIS文件:APHIS已发布的关于请求的各种文件,或可应要求从APHIS获得的各种文件。
可根据本发明处理的特别有用的转基因植物为包含一种或多种编码一种或多种毒素的基因的植物,例如以以下商品名出售的转基因植物:YIELD(例如,玉米、棉花、大豆)、(例如,玉米)、(例如,玉米)、(例如,玉米)、(例如,玉米)、(棉花)、(棉花)、Nucotn(棉花)、(例如,玉米),和(马铃薯)。可提及的除草剂耐受性植物的实例包括玉米品种、棉花品种和大豆品种,它们可以以下商品名获得:Roundup(耐受草甘膦,例如玉米、棉花、大豆)、Liberty(耐受草丁膦,例如油菜)、(耐受咪唑啉酮)和(耐受磺酰脲,例如玉米)。可提及的除草剂抗性植物(以常规方式培育以耐受除草剂的植物)包括以名称出售的品种(例如,玉米)。
以下实施例示意说明本发明。
实施例
通过以下实施例详细阐明本发明,但这些实施例不以任何方式限制本发明。
A.合成实施例
{[4-溴-5-(3,4-二氟苯基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸甲酯(I-15):向0.20g(0.54mmol)的4-溴-5-(3,4-二氟苯基)-1-(吡嗪-2-基)-1H-吡唑-3-醇在8ml的二甲基甲酰胺中的溶液中加入0.27g(0.81mmol)的碳酸铯,混合物于室温搅拌10分钟,加入0.10g(0.65mmol)的溴乙酸甲酯,并将混合物于室温搅拌一小时。过滤混合物,减压浓缩滤液,将残余物溶解在水中并用二氯甲烷反复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到0.23g(理论值的93%)的产物,m/z=427(50)[M+],425(50)[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):8.95(m,1H),8.38(m,1H),8.06(m,1H),7.22-7.17(m,2H),7.10-7.05(m,1H),4.97(s,2H),3.84(s,3H)。
起始化合物的合成:
a)4-溴-5-(3,4-二氟苯基)-1-(吡嗪-2-基)-1H-吡唑-3-醇:在氩气下向0.50g(1.07mmol)的2-[3-(苄氧基)-4-溴-5-(3,4-二氟苯基)-1H-吡唑-1-基]吡嗪中加入18.50g(162.25mmol)的三氟乙酸,并将混合物于回流下搅拌一小时。减压除去过量的三氟乙酸,将残余物溶解在二氯甲烷中,并减压除去溶剂。得到0.45g(理论值的95%)的无色固体,m/z=355(50)[M+],353(50)[M+]。
b)2-[3-(苄氧基)-4-溴-5-(3,4-二氟苯基)-1H-吡唑-1-基]吡嗪:向0.56g(1.50mmol)的2-[3-(苄氧基)-5-(3,4-二氟苯基)-1H-吡唑-1-基]吡嗪在8ml的DMF中的溶液中加入0.27g(1.50mmol)的N-溴琥珀酰亚胺,并将混合物于室温搅拌一小时。减压除去溶剂,将残余物溶解在水中并用二氯甲烷反复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到0.50g(理论值的71%)的产物,m/z(%)=445(50)[M+],443(50)[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):9.00(m,1H),8.38(m,1H),8.07(m,1H),7.56-7.52(m,2H),7.44-7.36(m,3H),7.22-7.16(m,2H),7.08-7.05(m,1H),5.44(s,2H)。
c)2-[3-(苄氧基)-5-(3,4-二氟苯基)-1H-吡唑-1-基]吡嗪:在氩气气氛下向1.50g(3.97mmol)的2-[3-(苄氧基)-5-碘-1H-吡唑-1-基]吡嗪在45ml的二噁烷中的溶液中依次加入1.14g(4.76mmol)的2-(3,4-二氟苯基)-4,4,5,5-四甲基-1,3,2-二氧杂环戊硼环、0.038g(0.20mmol)的碘化铜(I)、2.58g(7.93mmol)的碳酸铯、4.5ml的水和0.23g(0.20mmol)的四(三苯基膦)钯,并将反应混合物于70℃搅拌3小时。减压除去溶剂,将残余物溶解在水/乙酸乙酯中,水相用乙酸乙酯反复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到0.58g(38%)的淡黄色固体,m/z(%)=365[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):9.03(m,1H),8.39(m,1H),8.12(m,1H),7.52-7.49(m,2H),7.43-7.34(m,3H),7.18-7.11(m,2H),7.06-7.02(m,1H),6.03(s,1H),5.36(s,2H)。
d)2-[3-(苄氧基)-5-碘-1H-吡唑-1-基]吡嗪:在氩气气氛下向5.00g(15.86mmol)的2-[3-(苄氧基)-1H-吡唑-1-基]吡嗪在150ml的干燥四氢呋喃中的溶液中在-78℃下逐滴加入2.21g(20.61mmol)的二异丙基酰胺锂在50ml的四氢呋喃中的溶液(在四氢呋喃中的2M溶液),并将混合物于-78℃下搅拌0.5小时。逐滴加入5.23g(20.61mmol)的碘在50ml的四氢呋喃中的溶液,并将混合物于-78℃下再搅拌一小时。使混合物温热至室温,加入水,并用乙酸乙酯反复进行萃取。合并的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到1.84g(31%)的无色固体,m/z(%)=379[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):9.13(m,1H),8.50(m,1H),8.42(m,1H),7.48-7.45(m,2H),7.42-7.32(m,3H),6.26(s,1H),5.30(s,2H)。
e)2-[3-(苄氧基)-1H-吡唑-1-基]吡嗪:在氩气气氛下向6.87g(59.99mmol)的2-氯吡嗪在60ml的DMF中的溶液中依次加入24.88g(76.35mmol)的碳酸铯、溶解在40ml的DMF中的10.00g(54.54mmol)的3-(苄氧基)-1H-吡唑和1.45g(7.62mmol)的碘化铜(I),并将反应混合物于120℃下搅拌5小时。过滤混合物,并用二氯甲烷洗涤,并减压除去溶剂。将残余物溶解在氯化铵水溶液中并用二氯甲烷反复萃取,合并的有机相用硫酸钠干燥,并减压除去溶剂。得到17.00g(98%)的微绿色固体,m/z(%)=253[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):9.17(m,1H),8.38(m,1H),8.31(d,1H),8.28(m,1H),7.52-7.50(m,2H),7.42-7.34(m,3H),6.02(d,1H),5.35(s,2H)。
{[4-溴-5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸吡啶-2-基甲酯(I-70):向在3.0ml的二氯甲烷中的0.04g(0.36mmol)的吡啶-2-基甲醇中依次加入0.10g(0.25mmol)的{[4-溴-5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸(I-49)、0.05g(0.33mmol)的1H-苯并三唑-1-醇、0.06g(0.33mmol)的N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺盐酸盐和一刀尖的N,N-二甲基吡啶-4-胺,并将混合物于室温上搅拌一小时。向反应混合物中加入水和二氯甲烷,用二氯甲烷反复萃取水相,合并的有机相用硫酸钠干燥,并减压除去溶剂。在硅胶上用庚烷/乙酸乙酯梯度对所得粗产物进行柱色谱法纯化,得到0.08g(理论值的65%)的产物,m/z(%)=487(50)[M+],485(50)[M+]。1H-NMR(600MHz,CDCl3,δ,ppm):9.01(m,1H),8.61(m,1H),8.39(m,1H),8.22(m,1H),7.99(m,1H),7.85-7.81(m,1H),7.69-7.65(m,1H),7.39(m,1H),7.26-7.22(m,1H),7.03-7.00(m,1H),5.39(s,2H),5.09(s,2H)。
{[4-溴-5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸(I-49):向在7ml的四氢呋喃中的0.77g(1.82mmol)的{[4-溴-5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸乙酯(I-52)中加入0.13g(5.47mmol)的氢氧化锂在10ml的水中的溶液,并将混合物于65℃下搅拌2小时。减压除去溶剂,将残余物溶解在水中并用二氯甲烷萃取两次,并用2M盐酸将水相调节至pH=2-3并用二氯甲烷萃取两次。合并的有机相用硫酸钠干燥,并减压除去溶剂。得到无色固体(0.58g,理论值的76%)。1H-NMR(600MHz,DMSO-d6,δ,ppm):13.17(bs,1H),9.00(m,1H),8.52(m,1H),8.34(m,1H),8.20(m,1H),8.11-8.08(m,1H),7.33-7.31(m,1H),4.97(s,2H)。
{[4-溴-5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸乙酯(I-52):向0.81g(2.36mmol)的{[5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸乙酯在5ml的DMF中的溶液中加入0.50g(2.83mmol)的N-溴琥珀酰亚胺,并将混合物于室温下搅拌十小时。减压除去溶剂,将残余物溶解在水中并用二氯甲烷重复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯梯度纯化后,得到0.92g(理论值的87%)的产物,m/z(%)=424(50)[M+],422(50)[M+]。1H-NMR(600MHz,CDCl3,δ,ppm):9.05(m,1H),8.37(m,1H),8.23(m,1H),7.99(m,1H),7.86-7.82(m,1H),7.03-7.00(m,1H),4.96(s,2H),4.31(q,2H),1.34(t,3H)。
起始化合物的合成:
a){[5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸乙酯:向1.58g(5.84mmol)的5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-醇在10ml的二甲基甲酰胺中的溶液中加入2.85g(8.75mmol)的碳酸铯,混合物于室温搅拌10分钟,加入1.17g(7.00mmol)的溴乙酸乙酯,并将混合物于65℃下再搅拌两小时。过滤混合物,减压浓缩滤液,将残余物溶解在水中并用二氯甲烷重复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到1.53g(理论值的73%)的产物,m/z=344[M+]。1H-NMR(600MHz,CDCl3,δ,ppm):9.08(m,1H),8.37(m,1H),8.23(m,1H),8.02(m,1H),7.81-7.78(m,1H),6.96-6.94(m,1H),6.13(s,1H),4.91(s,2H),4.31(q,2H),1.33(t,3H)。
b)5-(6-氟吡啶-3-基)-1-(吡嗪-2-基)-1H-吡唑-3-醇:向3.55g(8.28mmol)的3-(6-氟吡啶-3-基)-N'-(吡嗪-2-基)丙-2-炔酰肼在7ml的乙腈中的溶液加入0.08g(0.66mmol)的碘化铜(I),并将混合物于80℃下搅拌两小时。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到1.59g(理论值的75%)的产物,m/z=258[M+]。1H-NMR(400MHz,DMSO-d6,δ,ppm):10.82(s,1H),9.00(m,1H),8.46(m,1H),8.29(m,1H),8.17(m,1H),8.02-7.97(m,1H),7.32-7.28(m,1H),6.18(s,1H)。
c)3-(6-氟吡啶-3-基)-N'-(吡嗪-2-基)丙-2-炔酰肼:向3.00g(16.35mmol)的3-(6-氟吡啶-3-基)丙-2-炔酸在20ml的四氢呋喃中的溶液依次加入2.07g(18.80mmol)的2-肼并吡嗪和8.27g(81.76mmol)的三乙胺。逐滴加入15.61g(24.53mmol)的丙烷膦酸酐(T3P,在四氢呋喃中的50%溶液),并将混合物于室温搅拌一小时。将反应混合物倾倒到水上并用乙酸乙酯重复萃取,合并的有机相用硫酸钠干燥,减压除去溶剂,得到3.55g(理论值的51%)的油状产物(HPLC/MS纯度=60%,m/z=258[M+]),其不经纯化即进一步转化。
d)3-(6-氟吡啶-3-基)丙-2-炔酸:在氩气气氛下,向在105ml的干燥四氢呋喃中的9.20g(41.26mmol)的2-氟-5-碘吡啶中依次加入以下物质:2.89g(41.26mmol)的丙炔酸、0.58g(0.83mmol)的双(三苯基膦)二氯化钯(II)、0.31g(1.65mmol)的碘化铜(I)和14.61g(144.41mmol)的二异丙胺。混合物于室温下搅拌2小时,将反应混合物加到水中,加入30ml的2N盐酸并用乙酸乙酯反复进行萃取。合并的有机相用硫酸镁干燥,并减压浓缩。将残余物与乙醚混合,将混合物在超声浴中搅拌10分钟并过滤,并减压除去溶剂。得到6.25g(理论值的78%)的产物,m/z=166[M+]。1H-NMR(600MHz,DMSO-d6,δ,ppm):14.00(bs,1H),8.57(m,1H),8.32-8.28(m,1H),7.35-7.32(m,1H)。
(2R)-2-{[4-溴-1-(吡嗪-2-基)-5-(哒嗪-4-基)-1H-吡唑-3-基]氧基}丙酸甲酯(I-31):向0.71g(1.75mmol)的(2R)-2-{[1-(吡嗪-2-基)-5-(哒嗪-4-基)-1H-吡唑-3-基]氧基}丙酸甲酯在8ml的DMF中的溶液加入0.37g(2.10mmol)的N-溴琥珀酰亚胺,并将混合物于室温下搅拌三小时。减压除去溶剂,将残余物溶解在水中并用二氯甲烷重复萃取,干燥的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯梯度纯化后,得到0.14g(理论值的20%)的产物,m/z(%)=405(50)[M+],407(50)[M+],并且比旋光度[α]=+56°。1H-NMR(400MHz,CDCl3,δ,ppm):9.32(m,1H),9.14(m,1H),9.08(m,1H),8.40(m,1H),7.94(m,1H),7.55(m,1H),5.26(q,1H),3.83(s,3H),1.74(d,3H)。
(2R)-2-{[4-氰基-1-(吡嗪-2-基)-5-(哒嗪-4-基)-1H-吡唑-3-基]氧基}丙酸甲酯(I-32):在微波中于氩气气氛下将0.40g(0.79mmol)的(2R)-2-{[4-溴-1-(吡嗪-2-基)-5-(哒嗪-4-基)-1H-吡唑-3-基]氧基}丙酸甲酯(I-31)、0.09g(0.75mmol)的氰化锌和0.09g(0.08mmol)的四(三苯基膦)钯在10ml的二甲基乙酰胺中的混合物加热至180℃,保持40分钟。减压除去溶剂,将残余物溶解在水/二氯甲烷中,水相用二氯甲烷重复萃取,合并的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯梯度纯化后,得到0.21g(理论值的70%)的产物,m/z=352[M+],并且比旋光度[α]=+54°。1H-NMR(400MHz,CDCl3,δ,ppm):9.39(m,1H),9.15(m,1H),9.12(m,1H),8.54(m,1H),8.05(m,1H),7.64(m,1H),5.29(q,1H),3.83(s,3H),1.74(d,3H)。
N-烯丙基-2-{[4-溴-5-(3-氟苯基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酰胺(II-01):在氩气下向0.09g(0.23mmol)的{[4-溴-5-(3-氟苯基)-1-(吡嗪-2-基)-1H-吡唑-3-基]氧基}乙酸在5ml的四氢呋喃中的溶液依次加入0.01g(0.25mmol)的丙-2-烯-1-胺和在5ml的二氯甲烷中的0.05g(0.28mmol)的N-(3-二甲基氨基丙基)-N′-乙基碳二亚胺盐酸盐,并将混合物于室温下搅拌四小时。减压除去溶剂,将残余物溶解在二氯甲烷中,加入2N的盐酸,混合物用二氯甲烷重复萃取,合并的有机相用硫酸钠干燥,并减压除去溶剂。通过柱色谱法在硅胶上用庚烷/乙酸乙酯纯化后,得到0.03g(理论值的27%)的无色油,m/z(%)=434(50)[M+],432(50)[M+]。1H-NMR(400MHz,CDCl3,δ,ppm):8.94(m,1H),8.41(m,1H),8.10(m,1H),7.41-7.36(m,1H),7.16-7.05(m,2H),6.62(bs,1H),5.94-5.87(m,1H),5.30-5.25(m,1H),5.20-5.17(m,1H),4.93(s,2H),4.05-4.01(m,1H)。
所选实施例的NMR数据:
通式(I)的化合物的所选实施例的1H NMR数据以两种不同的方式陈述,即(a)常规NMR评价和解释或(b)根据下文描述方法的1H NMR峰列表的形式。
a)常规NMR解释
实施例I-08:
1H-NMR(400MHz,CDCl3,δ,ppm):9.03(m,1H),8.52(m,1H),8.39-8.37(m,2H),7.98(m,1H),7.51-7.48(m,1H),5.27(q,1H),3.82(s,3H),1.73(d,3H)。
实施例I-15:
1H-NMR(400MHz,CDCl3,δ,ppm):8.95(m,1H),8.38(m,1H),8.06(m,1H),7.22-7.17(m,2H),7.10-7.05(m,1H),4.97(s,2H),3.84(s,3H)。
实施例I-27:
1H-NMR(400MHz,CDCl3,δ,ppm):9.01(m,1H),8.82(d,2H),8.33(m,1H),7.90(m,1H),7.32(t,1H),5.29(q,1H),3.80(s,3H),1.72(d,3H)。
实施例I-31:
1H-NMR(400MHz,CDCl3,δ,ppm):9.32(m,1H),9.14(m,1H),9.08(m,1H),8.40(m,1H),7.94(m,1H),7.55(m,1H),5.26(q,1H),3.83(s,3H),1.74(d,3H)。
实施例I-32:
1H-NMR(400MHz,CDCl3,δ,ppm):9.39(m,1H),9.15(m,1H),9.12(m,1H),8.54(m,1H),8.05(m,1H),7.64(m,1H),5.29(q,1H),3.83(s,3H),1.74(d,3H)。
实施例I-36:
1H-NMR(400MHz,CDCl3,δ,ppm):9.03(m,1H),8.37(m,1H),8.24(m,1H),7.99(m,1H),7.86-7.82(m,1H),7.03-7.00(m,1H),5.27(q,1H),3.82(s,3H),1.73(d,3H)。
实施例I-49:
1H-NMR(600MHz,DMSO-d6,δ,ppm):13.17(bs,1H),9.00(m,1H),8.52(m,1H),8.34(m,1H),8.20(m,1H),8.11-8.08(m,1H),7.33-7.31(m,1H),4.97(s,2H)。
实施例I-52:
1H-NMR(600MHz,CDCl3,δ,ppm):9.05(m,1H),8.37(m,1H),8.23(m,1H),7.99(m,1H),7.86-7.82(m,1H),7.03-7.00(m,1H),4.96(s,2H),4.31(q,2H),1.34(t,3H)。
实施例I-54:
1H-NMR(400MHz,CDCl3,δ,ppm):9.1(s,1H),8.9(d,2H),8.4(s,1H),7.9(s,1H),7.4(m,1H),5.2(q,1H),1.7(d,3H)。
实施例I-55:
1H-NMR(400MHz,CDCl3,δ,ppm):9.1(s,1H),8.7(d,2H),8.5(s,1H),8.1(s,1H),7.4(m,1H),5.4(q,1H),1.8(d,3H)。
实施例I-70:
1H-NMR(600MHz,CDCl3,δ,ppm):9.01(m,1H),8.61(m,1H),8.39(m,1H),8.22(m,1H),7.99(m,1H),7.85-7.81(m,1H),7.69-7.65(m,1H),7.39(m,1H),7.26-7.22(m,1H),7.03-7.00(m,1H),5.39(s,2H),5.09(s,2H)。
实施例I-78:
1H-NMR(400MHz,CDCl3,δ,ppm):8.18-8.14(m,3H),7.86-7.82(m,1H),7.00-6.97(m,1H),5.23(q,1H),3.79(s,3H),1.70(d,3H)。
实施例I-80:
1H-NMR(400MHz,CDCl3,δ,ppm):8.18-8.14(m,3H),7.86-7.82(m,1H),7.00-6.97(m,1H),5.23(q,1H),3.79(s,3H),1.70(d,3H)。
实施例I-83:
1H-NMR(400MHz,DMSO-d6,δ,ppm):13.01(bs,1H),8.94(s,1H),8.42(m,1H),8.30(m,1H),8.12(m,1H),8.06-8.02(m,1H),7.28-7.25(m,1H),4.88(s,2H),1.56-1.49(m,1H),0.73-0.63(m,4H)。
实施例I-84:
1H-NMR(400MHz,CDCl3,δ,ppm):9.00(s,1H),8.27(m,1H),8.23(m,1H),7.93(m,1H),7.83-7.78(m,1H),7.00-6.97(m,1H),4.92(s,2H),3.83(s,3H),1.49-1.43(m,1H),0.83-0.79(m,2H),0.76-0.71(m,2H)。
实施例I-85:
1H-NMR(400MHz,CDCl3,δ,ppm):9.00(s,1H),8.27(m,1H),8.23(m,1H),7.93(m,1H),7.83-7.78(m,1H),7.00-6.97(m,1H),4.90(s,2H),4.29(q,2H),1.48-1.43(m,1H),1.33(t,3H),0.84-0.80(m,2H),0.76-0.71(m,2H)。
实施例I-86:
1H-NMR(400MHz,CDCl3,δ,ppm):9.04(s,1H),8.22(m,2H),7.95(s,1H),7.81-7.76(m,1H),7.00-6.96(m,1H),5.20(q,1H),1.72(d,3H),1.47-1.40(m,1H),0.90-0.80(m,2H),0.77-0.72(m,2H)。
实施例I-87:
1H-NMR(400MHz,CDCl3,δ,ppm):8.98(s,1H),8.26(m,1H),8.23(m,1H),7.91(m,1H),7.82-7.78(m,1H),6.99-6.96(m,1H),5.23(q,1H),3.80(s,3H),1.66(d,3H),1.48-1.43(m,1H),0.87-0.82(m,2H),0.74-0.72(m,2H)。
实施例I-88:
1H-NMR(400MHz,CDCl3,δ,ppm):8.99(s,1H),8.25(m,1H),8.23(m,1H),7.91(m,1H),7.82-7.78(m,1H),6.99-6.96(m,1H),5.20(q,1H),4.30-4.22(m,2H),1.66(d,3H),1.48-1.41(m,1H),1.31(t,3H),0.87-0.84(m,2H),0.75-0.71(m,2H)。
实施例I-89:
1H-NMR(400MHz,CDCl3,δ,ppm):9.03(m,1H),8.34(m,1H),8.20(m,1H),7.96(m,1H),7.83-7.78(m,1H),7.03-7.00(m,1H),5.25(q,1H),3.82(s,3H),1.72(d,3H)。
实施例II-01:
1H-NMR(400MHz,CDCl3,δ,ppm):8.94(m,1H),8.41(m,1H),8.10(m,1H),7.41-7.36(m,1H),7.16-7.05(m,2H),6.62(bs,1H),5.94-5.87(m,1H),5.30-5.25(m,1H),5.20-5.17(m,1H),4.93(s,2H),4.05-4.01(m,1H)。
实施例II-02:
1H-NMR(400MHz,CDCl3,δ,ppm):9.09(m,1H),8.40(m,1H),8.24(m,1H),8.00(m,1H),7.86-7.81(m,1H),7.04-7.01(m,2H),5.31(q,1H),3.68-3.55(m,2H),3.66(s,3H),2.60-2.57(m,2H),1.72(d,3H)。
实施例II-03:
1H-NMR(400MHz,CDCl3,δ,ppm):9.10(m,1H),8.41(m,1H),8.24(m,1H),8.01(m,1H),7.86-7.81(m,1H),7.04-7.01(m,2H),5.40(q,1H),4.17-4.10(m,2H),3.78(s,3H),1.75(d,3H)。
实施例II-04:
1H-NMR(400MHz,CDCl3,δ,ppm):9.09(m,1H),8.40(m,1H),8.24(m,1H),8.00(m,1H),7.86-7.81(m,1H),7.04-7.01(m,2H),5.32(q,1H),4.16-4.08(m,2H),3.67-3.58(m,2H),2.58-2.55(m,2H),1.72(d,3H),1.23(t,3H)。
实施例II-05:
1H-NMR(400MHz,CDCl3,δ,ppm):9.09(m,1H),8.39(m,1H),8.24-8.21(m,1H),8.00(m,1H),7.86-7.81(m,1H),7.10-7.00(m,2H),5.33-5.24(m,1H),4.47-4.38(m,1H),3.68/3.66(2s,3H),2.93-2.85(m,1H),2.28-2.19(m,1H),2.04-1.93(m,3H),1.90-1.68(m,5H)。
实施例II-06:
1H-NMR(400MHz,CDCl3,δ,ppm):9.10(m,1H),8.41(m,1H),8.24(m,1H),8.01(m,1H),7.86-7.81(m,1H),7.04-7.00(m,1H),6.62(bm,1H),5.34(q,1H),3.25-3.18(m,2H),1.74(d,3H),1.05-0.95(m,1H),0.54-0.50(m,2H),0.25-0.22(m,2H)。
实施例II-07:
1H-NMR(400MHz,CDCl3,δ,ppm):9.10(m,1H),8.42(m,1H),8.24(m,1H),8.01(m,1H),7.86-7.81(m,1H),7.08(bt,1H),7.04-7.01(m,1H),4.90(s,2H),3.69(s,3H),3.67(q,2H),2.62(t,2H)。
实施例II-08:
1H-NMR(400MHz,CDCl3,δ,ppm):9.11(m,1H),8.42(m,1H),8.24(m,1H),8.02(m,1H),7.86-7.82(m,1H),7.04-7.00(m,2H),4.96(s,2H),4.18(d,2H),3.80(s,3H)。
实施例II-09:
1H-NMR(400MHz,CDCl3,δ,ppm):9.10(m,1H),8.41(m,1H),8.23(m,1H),8.01(m,1H),7.86-7.81(m,1H),7.09(bt,1H),7.04-7.01(m,1H),4.90(s,2H),4.17(q,2H),3.67(q,2H),2.61(t,2H),1.26(t,3H)。
实施例II-10:
1H-NMR(400MHz,CDCl3,δ,ppm):9.11(m,1H),8.41(m,1H),8.24(m,1H),8.02(m,1H),7.86-7.81(m,1H),7.04-7.01(m,1H),6.62(bs,1H),4.91(s,2H),3.27(m,2H),1.06-1.02(m,1H),0.58-0.53(m,2H),0.29-0.26(m,2H)。
实施例II-11:
1H-NMR(400MHz,CDCl3,δ,ppm):9.10(m,1H),8.40(m,1H),8.23(m,1H),8.01(m,1H),7.86-7.82(m,1H),7.17(bd,1H),7.04-7.01(m,1H),4.89(s,2H),4.55-4.48(m,1H),3.68(s,3H),2.98-2.95(m,1H),2.28-2.20(m,1H),2.08-1.82(m,4H),1.81-1.73(m,1H)。
实施例II-12:
1H-NMR(400MHz,CDCl3,δ,ppm):9.08(s,1H),8.58(bs,1H),8.44(m,1H),8.24(m,1H),8.04(m,1H),7.88-7.83(m,1H),7.07-7.03(m,1H),4.96(s,2H),3.02(s,6H)。
实施例II-13:
1H-NMR(400MHz,CDCl3,δ,ppm):9.07(s,1H),8.75(bs,1H),8.44(m,1H),8.24(m,1H),8.04(m,1H),7.87-7.82(m,1H),7.05-7.02(m,1H),4.93(s,2H),4.25(q,1H),2.93(s,3H),1.17(d,6H)。
实施例II-14:
1H-NMR(400MHz,CDCl3,δ,ppm):9.07(s,1H),8.71(bs,1H),8.44(m,1H),8.24(m,1H),8.05(m,1H),7.87-7.82(m,1H),7.06-7.03(m,1H),5.01(s,2H),3.40(s,3H)。
b)NMR峰列表方法
所选实施例的1H NMR数据以1H NMR峰列表的形式陈述。对于每个信号峰,首先列出以ppm计的δ值,然后在圆括号中列出信号强度。不同信号峰的δ值-信号强度数对用分号彼此分隔列出。
因此,一个实施例的峰列表呈以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖峰信号的强度与NMR谱的打印实例中以cm计的信号高度相关,并示出了信号强度的真实比率。在宽峰信号的情况下,可示出信号的几个峰或中间部分及其与谱图中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/或溶剂的化学位移,特别是在DMSO中测量的谱图的情况下。因此,在NMR峰列表中,四甲基硅烷峰可能但不一定出现。
1H NMR峰的列表与常规的1H NMR打印输出类似并因此通常包括在常规NMR解释中列出的所有峰。
另外,它们还与常规的1H NMR打印输出一样显示溶剂信号、同样由本发明提供的目标化合物的立体异构体和/或杂质峰的信号。
在报告溶剂和/或水的δ范围内的化合物信号时,我们的1H NMR峰列显示出标准溶剂峰,例如DMSO-D6中DMSO的峰和水的峰,平均来看它们通常具有高强度。
与目标化合物(例如具有>90%的纯度)的峰相比,目标化合物的立体异构体的峰和/或杂质的峰通常平均具有较低的强度。
这样的立体异构体和/或杂质可能是特定的制备方法所特有的。因此,它们的峰可有助于参考“副产物指纹”来识别我们的制备方法的重现性。
如果需要,通过已知方法(MestreC、ACD模拟以及用经验评估的预期值)计算目标化合物的峰的专业人员可任选地使用额外的强度滤波器来分离目标化合物的峰。该分离会与在常规的1H NMR解释中讨论的挑选峰类似。
1H NMR峰列表的更多细节可见于Research Disclosure Database564025号。
B.制剂实施例
a)通过将10重量份的式(I)化合物和/或其盐与作为惰性物质的90重量份的滑石混合并在冲击磨中粉碎所述混合物来获得喷粉产物。
b)通过混合25重量份的式(I)化合物和/或其盐、作为惰性物质的64重量份的含高岭土石英、作为润湿剂和分散剂的10重量份的木质素磺酸钾和1重量份的油酰甲基牛磺酸钠并在针盘磨机中研磨来获得易于在水中分散的可湿性粉剂。
c)通过混合20重量份的式(I)化合物和/或其盐与6重量份的烷基酚聚二醇醚(Triton X 207)、3重量份的异十三醇聚二醇醚(8EO)和71重量份的石蜡矿物油(沸程例如约255至277℃以上)并在碾磨球磨机中研磨至低于5微米的细度来获得易于在水中分散的分散体浓缩物。
d)由15重量份的式(I)化合物和/或其盐、作为溶剂的75重量份的环己酮和作为乳化剂的10重量份的乙氧基化壬基酚得到可乳化浓缩物。
e)通过混合以下:
75重量份的式(I)化合物和/或其盐,
10重量份的木质素磺酸钙、
5重量份的月桂基硫酸钠、
3重量份的聚乙烯醇和
7重量份的高岭土,
在针盘磨机中研磨所述混合物并在流化床中通过喷洒水作为造粒液对所述粉末造粒来获得水分散性颗粒。
f)还通过在胶体磨中均质化并预粉碎以下:
25重量份的式(I)的化合物和/或其盐、
5重量份的2,2’-二萘基甲烷-6,6’-二磺酸钠、
2重量份的油酰甲基牛磺酸钠、
1重量份的聚乙烯醇、
17重量份的碳酸钙和
50重量份的水,
然后在珠磨机中研磨所述混合物并在喷雾塔中借助于单相喷嘴雾化和干燥所得悬浮液来获得水分散性颗粒。
C.生物学实施例
在下面的表A1至A21和B1至B21中,使用了以下缩写:
1.出苗后除草作用
a)将单子叶和双子叶杂草和作物植物的种子放在塑料或有机花盆中的砂壤土中,用土壤覆盖并在温室中于受控的生长条件下培育。播种后2至3周,在单叶期处理试验植物。然后将以可湿性粉剂(WP)的形式或作为乳液浓缩物(EC)配制的本发明化合物以添加0.5%的添加剂的水悬浮液或乳液喷洒到所述植物的绿色部分上,水施用量为600l/ha(换算的)。在试验植物在温室中于最佳生长条件下保持约3周后,采取目测方式与未处理的对照相比,对所述制剂的活性进行评定。例如,100%活性=植物已死亡,0%活性=与对照植物一样。
下面的表A1至A15示出了根据表1和2选择的通式(I)化合物及对应于320g/ha和/或80g/ha的施用量对各种有害植物的效果,其通过上述实验程序获得。
表A1.对ALOMY的出苗后作用(%)
表A2:对AVEFA的出苗后作用(%)
表A3:对DIGSA的出苗后作用(%)
表A4:对ECHCG的出苗后作用(%)
表A5:对LOLRI的出苗后作用(%)
表A6:对SETVI的出苗后作用(%)
表A7:对ABUTH的出苗后作用(%)
表A8:对AMARE的出苗后作用(%)
表A9:对MATIN的出苗后作用(%)
表A10:对PHBPU的出苗后作用(%)
表A11:对POLCO的出苗后作用(%)
表A12:对STEME的出苗后作用(%)
表A13:对VIOTR的出苗后作用(%)
表A14:对VERPE的出苗后作用(%)
表A15:对HORMU的出苗后作用(%)
如结果所示,本发明的化合物,例如化合物编号I-01、I-05、I-07、I-08、I-10、I-11、I-12、I-15、I-16、I-17、I-20、I-22、I-34、I-36、I-37、I-39、I-40、I-45和I-53以及来自表A1至A15的其他化合物在出苗后处理的情况下对有害植物显示出良好的除草功效。例如,在0.32kg活性物质每公顷的施用量下,化合物编号I-05、I-07、I-08、I-10、I-12、I-16、I-17、I-22、I-36、I-37、I-39和I-40在出苗后方法中对有害植物如大穗看麦娘、反枝苋、野燕麦、硬直黑麦草、卷茎蓼、狗尾草、阿拉伯婆婆纳和三色堇具有非常好的作用(80%至100%的除草活性)。
b)将单子叶和双子叶杂草植物的种子放在塑料盆中的砂壤土中(每盆用单子叶或双子叶杂草植物中的各一个物种双播种),用土壤覆盖并在温室中于受控的生长条件下培育。播种后2至3周,在单叶期处理试验植物。将以可湿性粉剂(WP)的形式或作为乳液浓缩物(EC)配制的本发明化合物以添加0.5%的添加剂的水悬浮液或乳液施用于植物的绿色部分,水施用量等于600升每公顷。在让试验植物在温室中于最佳生长条件下保持约3周后,采取目测方式与未处理的对照相比,对所述制剂的活性进行评定。例如,100%活性=植物已死亡,0%活性=与对照植物一样。
下面的表A16至A21示出了根据表1和2选择的通式(I)化合物在对应于1280g/ha的施用量下对各种有害植物的效果,其通过上述实验程序获得。
表A16:在1280g/ha下对POAAN的出苗后作用(%)
表A17:在1280g/ha下对DIGSA的出苗后作用(%)
表A18:在1280g/ha下对ECHCG的出苗后作用(%)
表A19:在1280g/ha下对ABUTH的出苗后作用(%)
表A20:在1280g/ha下对MATIN的出苗后作用(%)
表A21:在1280g/ha下对STEME的出苗后作用(%)
如结果所示,在1.28kg活性物质每公顷的施用量下,通式(I)的本发明化合物在出苗后处理中对有害植物如苘麻、棉田马唐、稗、淡甘菊、早熟禾、繁缕具有非常好的除草功效(90%至100%的除草活性)。
因此,本发明的化合物对广谱的禾本科杂草和阔叶杂草具有良好的除草作用并因此适合于通过出苗后方法防治不需要的植物。
2.出苗前除草作用
a)将单子叶和双子叶杂草植物和作物植物的种子放在塑料或有机花盆中并用土壤覆盖。然后将以可湿性粉剂(WP)的形式或作为乳液浓缩物(EC)配制的本发明化合物以添加0.5%的添加剂的水悬浮液或乳液施用到覆盖土壤的表面上,水施用量为600l/ha(换算的)。处理后,将盆放在温室中并保持在对试验植物良好的生长条件下。约3周后,采取目测方式与未处理的对照相比,对所述制剂的效果以百分比打分。例如,100%活性=植物已死亡,0%活性=与对照植物一样。
下面的表B1至B15示出了根据表1和2选择的通式(I)化合物及对应于320g/ha和/或80g/ha的施用量对各种有害植物的效果,其通过上述实验程序获得。
表B1:对ALOMY的出苗前作用(%)
表B2:对AVEFA的出苗前作用(%)
表B3:对DIGSA的出苗前作用(%)
表B4:对ECHCG的出苗前作用(%)
表B5:对LOLRI的出苗前作用(%)
表B6:对SETVI的出苗前作用(%)
表B7:对ABUTH的出苗前作用(%)
表B8:对AMARE的出苗前作用(%)
表B9:对MATIN的出苗前作用(%)
表B10:对PHBPU的出苗前作用(%)
表B11:对POLCO的出苗前作用(%)
表B12:对STEME的出苗前作用(%)
表B13:对VIOTR的出苗前作用(%)
表B14:对VERPE的出苗前作用(%)
表B15:对HORMU的出苗前作用(%)
如结果所示,本发明的化合物,例如化合物编号I-01、I-05、I-07、I-08、I-11、I-12、I-13、I-15、I-16、I-17、I-20、I-22、I-34、I-36、I-37、I-39、I-45、I-46、I-48、I-52和I-53以及来自表B1至B15的其他化合物在出苗前处理的情况下对有害植物显示出良好的除草功效。例如,在0.32kg活性物质每公顷的施用量下,化合物编号I-07、I-08、I-11、I-12、I-13、I-16、I-17、I-20、I-36、I-37、I-39、I-45、I-46、I-48、I-52和I-53在出苗前方法中对有害植物如大穗看麦娘、反枝苋、棉田马唐、硬直黑麦草、卷茎蓼、狗尾草、阿拉伯婆婆纳和三色堇具有非常好的作用(80%至100%的除草活性)。
b)将单子叶和双子叶杂草植物的种子放在塑料盆中的砂壤土中(每盆用单子叶或双子叶杂草植物中的各一个物种双播种)并用土壤覆盖。然后将以可湿性粉剂(WP)的形式或作为乳液浓缩物(EC)配制的本发明化合物以添加0.5%的添加剂的水悬浮液或乳液施用到覆盖土壤的表面上,水施用量等于600升每公顷。处理后,将盆放在温室中并保持在对试验植物良好的生长条件下。约3周后,采取目测方式与未处理的对照相比,对所述制剂的效果以百分比打分。例如,100%活性=植物已死亡,0%活性=与对照植物一样。
下面的表B16至B21示出了根据表1和2选择的通式(I)化合物在对应于1280g/ha的施用量下对各种有害植物的效果,其通过上述实验程序获得。
表B16:在1280g/ha下对POAAN的出苗前作用(%)
表B17:在1280g/ha下对DIGSA的出苗前作用(%)
表B18:在1280g/ha下对ECHCG的出苗前作用(%)
表B19:在1280g/ha下对AMARE的出苗前作用(%)
表B20:在1280g/ha下对MATIN的出苗前作用(%)
表B21:在1280g/ha下对STEME的出苗前作用(%)
如结果所示,在1.28kg活性物质每公顷的施用量下,通式(I)的本发明化合物在出苗前处理中对有害植物如反枝苋、棉田马唐、稗、淡甘菊、早熟禾、繁缕具有非常好的除草功效(90%至100%的除草活性)。
因此,本发明的化合物对广谱的禾本科杂草和阔叶杂草具有良好的除草作用并因此适合于通过出苗前方法防治不需要的植物。
Claims (14)
1.通式(I)的取代的1-吡嗪基吡唑基-3-氧基烷基酸及其农用化学上可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,
其中
A为A1-A28:
R1为
-OR1a或
-NR9R10;其中
R1a
-为氢;
-为(C1-C12)-烷基,其未被取代或被一个或多个选自卤素、(C3-C6)-环烷基、(C1-C4)-三烷基甲硅烷基、(C1-C6)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、氰基和硝基的取代基所取代;
-为(C2-C6)-烯基、(C2-C6)-卤代烯基;
-为(C2-C6)-炔基;
-为(C3-C6)-环烷基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C3-C6)-环烷基的取代基所取代;
-为(C1-C4)-烷基-SO-(C1-C4)-烷基、(C1-C4)-烷基-SO2-(C1-C4)-烷基;
-为杂环基、杂芳基和芳基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为杂环基-(C1-C4)-烷基、杂芳基-(C1-C4)-烷基和芳基-(C1-C4)-烷基,其中所述杂环基、杂芳基和芳基未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为(C1-C6)-亚烷基氨基;
R9为氢和(C1-C12)-烷基;
R10
-为氢;
-为芳基、杂芳基、杂环基,其未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-为(C3-C7)-环烷基-(C1-C4)-烷基、杂环基-(C1-C4)-烷基、杂芳基-(C1-C4)-烷基、芳基-(C1-C4)-烷基、芳基-(C1-C4)-烷氧基;
其中所述环烷基、杂环基、杂芳基和芳基未被取代或者被一个或多个选自卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基的取代基所取代;
-(C1-C12)-烷基;(C3-C8)-环烷基、(C2-C12)-烯基、(C5-C8)-环烯基、(C2-C12)-炔基;
其中上述烷基、环烷基、烯基、环烯基和炔基基团未被取代或各自独立地被m个选自氰基、硝基、OR5、S(O)nR5、SO2NR6R7、C(O)OR8、CONR6R8、COR6、NR6R8、NR6COR8、NR6CONR8R8、NR6CO2R8、NR6SO2R8、NR6SO2NR6R8、C(R6)=NOR8的基团所取代;
-为(C1-C12)-卤代烷基;
-为S(O)nR5、氰基、硝基、OR5、SO2NR6R7、CO2R8、COR8、NR6R8、NR6COR8、NR6CO2R8、NR6SO2R8;
或
R9和R10与它们所键合的氮原子一起形成饱和的或者部分或完全不饱和的五元、六元或七元环,所述环任选被选自卤素、(C1-C6)-烷基、卤素-(C1-C6)-烷基、OR5、S(O)nR5、CO2R8、CONR6R8、COR6和C(R6)=NOR8的基团单取代至六取代,并且,除该氮原子外,所述环还含有r个碳原子、o个氧原子、p个硫原子和q个来自NR7、CO和NCOR7的元素作为环原子;
R5为(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基、(C2-C4)-烯基或芳基;
R6为氢或R5;
R7为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C2-C4)-烯基或(C3-C4)-炔基;
R8为氢、(C1-C6)-烷基、(C3-C6)-环烷基、(C3-C4)-烯基或(C3-C4)-炔基;
R2a为
-氢、卤素、氰基;
-(C1-C6)-烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基;
-(C2-C6)-烯基、(C2-C6)-卤代烯基;
-(C2-C6)-炔基、(C2-C6)-卤代炔基;
-(C3-C6)-环烷基;
R2b为
-氢和(C1-C4)-烷基;
R3为
-卤素、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C4)-烷氧基羰基;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-(C1-C2)-烷基-S(O)n和(C1-C2)-卤代烷基-S(O)n;
-CHO、C(O)NH2;
-NH2;
R4为
-卤素、氰基、异氰基、硝基;
-(C1-C6)-烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷基、(C1-C3)-卤代烷氧基;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-(C1-C4)-烷基-S(O)n、(C1-C4)-卤代烷基-S(O)n;
-CHO、(C1-C4)-烷基羰基、(C1-C4)-卤代烷基羰基、(C1-C4)-烷氧基羰基;
-NH2;
R12为
-卤素、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基羰基、(C1-C6)-卤代烷基羰基、(C1-C4)-烷氧基羰基、(C1-C6)-烷氧基、(C1-C3)-卤代烷氧基、(C1-C4)-烷基-S(O)n;
-(C2-C3)-烯基、(C2-C3)-卤代烯基;
-(C2-C3)-炔基、(C2-C3)-卤代炔基;
-NH2;
并且其中指数如下:
l为0、1、2或3;
m为0、1或2;
n为0、1或2;
o为0、1或2;
p为0或1;
q为0或1;
r为3、4、5或6;和
s为0、1、2、3、4或5。
2.根据权利要求1所述的式(I)的化合物及其农用化学上可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中
A为A1-A16:
R1为
-OR1a或
-NR9R10;其中
R1a
-为氢;
-为(C1-C6)-烷基,其未被取代或者被一个或多个选自卤素、(C3-C6)-环烷基、(C1-C4)-烷氧基、(C1-C2)-烷氧基-(C1-C4)-烷氧基、氰基和硝基的取代基所取代;
-为(C2-C6)-烯基、(C2-C6)-卤代烯基;
-为芳基-(C1-C2)-烷基、杂芳基-(C1-C2)-烷基,其中所述芳基和杂芳基未被取代或者被一个或多个选自卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基的取代基所取代;
-为(C1-C4)-亚烷基氨基;
R9为氢和(C1-C6)-烷基;
R10
-为氢;
-为(C3-C7)-环烷基-(C1-C4)-烷基、芳基-(C1-C4)-烷基、芳基-(C1-C4)-烷氧基,
其中所述环烷基和芳基未被取代或者被一个或多个选自卤素、(C1-C4)-烷基、(C1-C4)-卤代烷基的取代基所取代;
-为(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基;(C3-C8)-环烷基;
其中上述烷基、环烷基、烯基、环烯基和炔基基团未被取代或各自独立地被m个选自以下的基团所取代:
氰基、C(O)OR8;
-为(C1-C6)-卤代烷基;
-为S(O)2R5、SO2NR6R7、NR6SO2R8;
R5为(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基、(C2-C4)-烯基或芳基;
R6为氢、(C1-C4)-烷基或(C3-C6)-环烷基;
R7为氢、(C1-C4)-烷基或(C3-C6)-环烷基;
R8为氢、(C1-C6)-烷基、(C3-C6)-环烷基;
R2a为
-氢、氰基;
-(C1-C6)-烷基;
-(C3-C6)-环烷基;
R2b为氢;
R3为
-氟、氯、溴、碘、氰基、异氰基、NO2;
-(C1-C6)-烷基、(C3-C6)-环烷基、(C1-C6)-卤代烷基;
R4为
-氟、氯、溴、氰基;
-甲基、乙基;
-甲氧基、乙氧基;
R12为
-卤素、氰基、硝基;
-甲基、乙基、(C1-C2)-卤代烷基;
-甲氧基、乙氧基;
并且其中指数如下:
l为0、1或2;
m为0、1或2;
s为0、1、2、3。
3.根据权利要求1或2所述的式(I)的化合物及其农用化学上可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中:
A为A1-A10:
R1为
-OR1a或
-NR9R10;其中
R1a
-为氢;
-为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为1-丙烯基、2-丙烯基;
-为苄基、吡啶基甲基,其中苯基和吡啶基基团在每种情况下未被取代或被卤素所取代;
-为异亚丙基氨基;
R9为氢;
R10
-为氢;
-为环丙基甲基;
-为苄基、1-苯基乙基、2-苯基乙基、苄氧基,其中所述四个基团的每一个中的苯基基团未被取代或被卤素所取代;
-为甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基,其中上述基团未被取代或被C(O)OR8基团单取代;
-为环丙基、环丁基、环戊基,其中所述三个基团未被取代或被C(O)OR8基团单取代;
-为1-丙烯基、2-丙烯基、2-甲基-2-丙烯基、丙-2-炔-1-基、丁-2-炔-1-基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、丙基、1-甲基乙基、三氟甲基、1,1-二氟乙基、2,2,2-三氟乙基、环丙基或乙烯基;
R6为氢、甲基、乙基、丙基、1-甲基乙基或环丙基;
R7为氢或甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3为
-氟、氯、溴、碘、氰基、NO2;
-环丙基、三氟甲基;
R4为
-氟、氯、溴;
-甲基;
R12为
-氟、氯、溴;
并且其中指数如下:
l为0或1;
s为0、1或2。
4.根据权利要求1至3中任一项所述的式(I)的化合物及其农用化学上可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中:
A为A1、A3、A4、A5或A6:
R1为
-OR1a或
-NR9R10;其中
R1a
-为氢;
-为甲基、乙基;
-为氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为吡啶-2-基甲基;
-为异亚丙基氨基;
R9为氢;
R10
-为被C(O)OR8单取代的环戊基;
-为环丙基甲基;
-为CH2C(O)OR8、CH2CH2C(O)OR8;
-为2-丙烯基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、三氟甲基、1,1-二氟乙基、环丙基或乙烯基;
R6为甲基、乙基、丙基或1-甲基乙基;
R7为氢或甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3选自
-氯、溴、碘、氰基、NO2;
-三氟甲基、环丙基;
R4为
-氟、氯;
R12为氟;
并且其中指数如下:
l为0或1;
s为0、1或2。
5.根据权利要求1至4中任一项所述的式(I)的化合物及其农用化学上可接受的盐、N-氧化物、水合物以及所述盐和N-氧化物的水合物,其中
A为A1-1、A1-2、A1-3、A3-1、A3-2、A3-3、A3-4、A4-1、A5-1或A5-2:
R1为
-OR1a或
-NR9R10;其中
R1a
-为氢;
-为甲基、乙基;
-为氰基甲基、2-甲氧基乙基、2-(2-甲氧基乙氧基)乙基;
-为吡啶-2-基甲基;
-为异亚丙基氨基;
R9为氢;
R10
-为被C(O)OR8单取代的环戊基;
-为环丙基甲基;
-为CH2C(O)OR8、CH2CH2C(O)OR8;
-为2-丙烯基;
-为S(O)2R5、SO2NR6R7;
R5为甲基、乙基、三氟甲基、环丙基或乙烯基;
R6为甲基、乙基或1-甲基乙基;
R7为甲基;
R8为氢、甲基、乙基;
R2a为
-氢;
-甲基;
R2b为氢;
R3为
-氯、溴、氰基、环丙基;
R4为
-3-氟、3-氯;
其中指数
l为0或1。
8.一种农用化学组合物,其包含
a)至少一种如权利要求1至6中的一项或多项所定义的通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物,和
b)作物保护中惯用的助剂和添加剂。
9.一种农用化学组合物,其包含
a)至少一种如权利要求1至6中的一项或多项所定义的通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物,
b)一种或多种组分a)之外的活性农用化学成分,和任选地
c)作物保护中惯用的助剂和添加剂。
10.一种防治不需要的植物或调节植物的生长的方法,其中向所述植物、种子或其中所述植物生长的区域施用有效量的至少一种如权利要求1至6中的一项或多项所定义的通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物。
11.如权利要求1至6中的一项或多项所定义的通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物用作除草剂或植物生长调节剂的用途。
12.根据权利要求11所述的用途,其中所述通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物用于防治有害植物或用于调节植物作物中的生长。
13.根据权利要求12所述的用途,其中所述作物植物为转基因或非转基因作物植物。
14.一种种子,其特征在于用如权利要求1至6中的一项或多项所定义的通式(I)的化合物或其农用化学上可接受的盐、N-氧化物、水合物、所述盐/N-氧化物的水合物或者如权利要求8和9中任一项所要求保护的农用化学组合物包衣。
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AR (1) | AR121971A1 (zh) |
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WO2024078871A1 (de) | 2022-10-14 | 2024-04-18 | Bayer Aktiengesellschaft | 1-pyridyl-5-phenylpyrazolyl-3-oxy- und -3-thioalkylsäuren und derivate und deren verwendung zur bekämpfung unerwünschten pflanzenwachstums |
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- 2021-04-26 WO PCT/EP2021/060784 patent/WO2021219527A1/de unknown
- 2021-04-26 BR BR112022021901A patent/BR112022021901A2/pt unknown
- 2021-04-26 US US17/921,719 patent/US20230167088A1/en active Pending
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- 2021-04-26 AU AU2021263052A patent/AU2021263052A1/en active Pending
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- 2021-04-26 EP EP21719935.5A patent/EP4143181A1/de active Pending
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EP4143181A1 (de) | 2023-03-08 |
CA3181349A1 (en) | 2021-11-04 |
AR121971A1 (es) | 2022-07-27 |
WO2021219527A1 (de) | 2021-11-04 |
US20230167088A1 (en) | 2023-06-01 |
AU2021263052A1 (en) | 2022-12-08 |
JP2023525978A (ja) | 2023-06-20 |
BR112022021901A2 (pt) | 2023-01-17 |
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