CN103874681B - 杀真菌性4‑取代的‑3‑{苯基[(杂环基甲氧基)亚氨基]甲基}‑1,2,4‑噁二唑‑5(4h)‑酮衍生物 - Google Patents
杀真菌性4‑取代的‑3‑{苯基[(杂环基甲氧基)亚氨基]甲基}‑1,2,4‑噁二唑‑5(4h)‑酮衍生物 Download PDFInfo
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明提供杀真菌性的式(I)所示4‑取代的‑3‑{苯基[(杂环基甲氧基)亚氨基]甲基}‑1,2,4‑噁二唑‑5(4H)‑酮衍生物
Description
发明描述
本发明涉及4-取代的-3-{苯基[(杂环基甲氧基)亚氨基]甲基}-1,2,4-噁二唑-5(4H)-酮衍生物、它们的制备方法、它们作为杀真菌剂活性剂的应用-尤其是以杀真菌剂组合物的形式、以及使用这些化合物或者组合物防控植物病原真菌(特别是植物的植物病原真菌)的方法。
在欧洲专利申请第1184382号中,公开了具有下式化学结构的某些杂环肟衍生物:
这不包括在本发明范围内。
在国际专利申请WO2009/130193中,公开了具有下式化学结构的某些肟基(hydroximoyl)-杂环衍生物:
其中Q是苯环,L1是亚甲基连接基团,且A是杂环。
在农业领域中人们一直高度关注新农药化合物的应用,以避免或防控对活性成分有耐药性的菌株的产生。同样人们高度关注使用比已知化合物活性更高的新型化合物,目标在于降低所使用的活性化合物的量,与此同时维持与已知化合物至少相当的有效性。本发明人现已发现一类具有上述效果或优点的新化合物。
因此,本发明提供式(I)的4-取代的-3-{苯基[(杂环基甲氧基)亚氨基]甲基}-1,2,4-噁二唑-5(4H)-酮衍生物,及其盐、N-氧化物、金属配合物、准金属配合物,或(E)和(Z)异构体,及其混合物。
(I)
其中
·X1代表氢原子、甲酰基基团、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C2-C8-烯基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷基羰基;
·A选自下组:A1和A2:
其中
-Z1代表氢原子、卤素原子、硝基基团、氨基基团、羟氨基基团、氰基基团、羧酸基团、经取代或未经取代的C1-C8-烷氧基氨基基团、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C3-C10-环烷基氨基、经取代或未经取代的C3-C10-环烯基氨基、经取代或未经取代的C5-C12-稠合的二环烷基氨基、经取代或未经取代的C5-C12-稠合的二环烯基氨基、经取代或未经取代的二-C1-C8-烷基氨基、经取代或未经取代的苯基氨基、经取代或未经取代的杂环基氨基或式QC(=U)NRa的基团
·其中:
-Q代表氢原子、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C2-C8-烯基、经取代或未经取代的C3-C8-环烯基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷氧基、经取代或未经取代的C2-C8-烯基氧基、经取代或未经取代的C2-C8-炔基氧基、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C1-C8-烷基次磺酰基、经取代或未经取代的C2-C8-烯基次磺酰基、经取代或未经取代的C2-C8-炔基次磺酰基、经取代或未经取代的芳基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的杂环基、经取代或未经取代的C5-C12-稠合二环烷基、经取代或未经取代的C5-C12-稠合二环烯基、经取代或未经取代的C5-C12-苯并稠合的碳环基、经取代或未经取代的C5-C12-苯并稠合的杂环基、经取代或未经取代的环烷氧基;经取代或未经取代的环烯基氧基、经取代或未经取代的芳氧基;经取代或未经取代的杂环基氧基、经取代或未经取代的C5-C12-稠合的二环烷氧基、经取代或未经取代的C5-C12-稠合的二环烯基氧基、经取代或未经取代的C5-C12-苯并稠合的碳环基氧基、经取代或未经取代的C5-C12-苯并稠合的杂环基氧基;
-U表示氧原子或硫原子;
-Ra代表氢原子、羟基基团、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C2-C8-烯基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷氧基、经取代或未经取代的C3-C10-环烯基、经取代或未经取代的C5-C12-稠合的二环烷基、经取代或未经取代的C5-C12-稠合的二环烯基、经取代或未经取代的芳基,或经取代或未经取代的杂环基、经取代或未经取代的C1-C8-烷基羰基、经取代或未经取代的芳氧基羰基、经取代或未经取代的C1-C8-烷氧基羰基;
-Z2、Z3和Z4独立地代表氢原子、卤素原子、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、C2-C8-烯基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷氧基;
·Y1~Y5独立地代表氢原子、卤素原子、硝基基团、氰基基团、经取代或未经取代的甲醛O-(C1-C8-烷基)肟、五氟-λ6-次磺酰基基团、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、具有1~5个卤素原子的经取代或未经取代的C1-C8-卤代烷基、C2-C8-烯基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷氧基、具有1~5个卤素原子的经取代或未经取代的C1-C8-卤代烷氧基、经取代或未经取代的C1-C8-烷基次磺酰基、经取代或未经取代的C2-C8-烯基氧基、经取代或未经取代的C3-C8-炔基氧基、经取代或未经取代的N-(C1-C8-烷氧基)-C1-C8-烷酰亚胺基(alkanimidoyl)、具有1~5个卤素原子的经取代或未经取代的N-(C1-C8-烷氧基)-C1-C8-卤代烷酰亚胺基、经取代或未经取代的C1-C8-烷氧基羰基、经取代或未经取代的C1-C8-烷基羰氧基、经取代或未经取代的C1-C8-烷基亚磺酰基、经取代或未经取代的C1-C8-烷基-磺酰基、经取代或未经取代的苯氧基、经取代或未经取代的苯基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的三(C1-C8-烷基)-甲硅烷氧基、经取代或未经取代的三(C1-C8-烷基)-甲硅烷基、经取代或未经取代的杂环基、经取代或未经取代的杂环基氧基。
本发明的任何化合物可依据该化合物中立体单元(根据IUPAC规则定义)的数目而以一种或多种立体异构体的形式存在。因而本发明同等地涉及所有立体异构体以及所有可能的立体异构体按所有比例的混合物。这些立体异构体可以根据本领域技术人员所熟知的方法进行分离。
需要注意的是,式(I)的4-取代的-3-{苯基[(杂环基甲氧基)亚氨基]甲基}-1,2,4-噁二唑-5(4H)-酮衍生物中存在的肟部分(moiety)的立体结构包括(E)或(Z)异构体,并且这些立体异构体形成本发明的部分。
依据本发明,以下通用术语一般按以下含义使用:
·卤素是指氟、氯、溴或碘;
·杂原子可以是氮、氧或硫;
·除非另有说明,否则,根据本发明取代的基团或取代基可被一个或多个下列基团或原子取代:卤素原子、硝基基团、羟基基团、氰基基团、氨基基团、次磺酰基基团、五氟-6-次磺酰基基团、甲酰基基团、甲醛O-(C1-C8-烷基)肟、甲酰基氧基基团、甲酰基氨基基团、甲酰基氨基基团、(羟基亚氨基)-C1-C6-烷基基团、C1-C8-烷基、三(C1-C8-烷基)甲硅烷基、C3-C8-环烷基、C3-C8-环烯基、具有1~5个卤素原子的C1-C8-卤代烷基、具有1~5个卤素原子的C1-C8-卤代环烷基、C2-C8-烯基、C2-C8-炔基、C2-C8-烯氧基、C2-C8-炔氧基、C1-C8-烷基氨基、二-C1-C8-烷基氨基、C1-C8-烷氧基、具有1~5个卤素原子的C1-C8-卤代烷氧基、C1-C8-烷基次磺酰基、具有1~5个卤素原子的C1-C8-卤代烷基次磺酰基、具有1~5个卤素原子的C2-C8-卤代烯氧基、具有1~5个卤素原子的C3-C8-卤代炔氧基、C1-C8-烷基羰基、具有1~5个卤素原子的C1-C8-卤代烷基羰基、C1-C8-烷基氨甲酰基、二-C1-C8-烷基氨甲酰基、N-C1-C8-烷基氧基氨甲酰基、C1-C8-烷氧基氨甲酰基、N-C1-C8-烷基-C1-C8-烷氧基氨甲酰基、C1-C8-烷氧基羰基、具有1~5个卤素原子的C1-C8-卤代烷氧基羰基、C1-C8-烷基羰氧基、具有1~5个卤素原子的C1-C8-卤代烷基羰氧基、C1-C8-烷基羰基氨基、具有1~5个卤素原子的C1-C8-卤代烷基羰基氨基、C1-C8-烷氧基羰基氨基、具有1~5个卤素原子的C1-C8-卤代烷氧基羰基氨基、C1-C8-烷基氨基羰氧基、二-C1-C8-烷基氨基羰氧基、C1-C8-烷基氧基羰氧基、(C1-C6-烷氧基亚氨基)-C1-C6-烷基、(C1-C6-烯氧基亚氨基)-C1-C6-烷基、(C1-C6-炔氧基亚氨基)-C1-C6-烷基、(苄氧基亚氨基)-C1-C6-烷基、C1-C8-烷氧基烷基、具有1~5个卤素原子的C1-C8-卤代烷氧基烷基、苄氧基、苄基次磺酰基、苄基氨基、苯氧基、苯基次磺酰基,或苯基氨基、芳基基团、杂环基基团;或者
·本发明的经取代的基团或取代基可以以下方式被取代:取代基团一起形成经取代或未经取代的、饱和或部分饱和的3-、4-、5-、6-、7-、8-、9-、10-或11-元环,其可以是包含至多4个杂原子的碳环或杂环,所述杂原子选自N、O和S
·术语“芳基”是指苯基或萘基;
·术语“杂环基”是指最多包含4个选自N、O、S的杂原子的、稠合或非稠合的、饱和或不饱和的4-、5-、6-、7-、8-、9-、10-、11-或12-元环。
本发明优选的式(I)化合物是:其中X1代表氢原子、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基或经取代或未经取代的C2-C8-烯基的那些。
本发明的更优选式(I)化合物是其中X1代表氢原子、甲基基团、乙基基团、正丙基基团、异丙基基团或环丙基基团的那些。
本发明的甚至更优选的式(I)化合物是其中X1代表氢原子或甲基基团的那些。本发明的其它优选的式(I)化合物是其中A代表A1的那些。
本发明的其它优选的式(I)化合物是这样一些化合物:其中Z1代表氢原子、卤素原子、硝基基团、氨基基团、羟基氨基基团、经取代或未经取代的C1-C8-烷氧基氨基基团、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C3-C10-环烷基氨基、经取代或未经取代的C3-C10-环烯基氨基、经取代或未经取代的C5-C12-稠合的二环烷基氨基、经取代或未经取代的C5-C12-稠合的二环烯基氨基、经取代或未经取代的二-C1-C8-烷基氨基、经取代或未经取代的苯基氨基、经取代或未经取代的杂环基氨基或式QC(=U)NRa的基团。
本发明的更优选的式(I)化合物是这样一些化合物:其中Z1代表氢原子、卤素原子、硝基基团、氨基基团、经取代或未经取代的C1-C8-烷氧基氨基基团、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C3-C10-环烷基氨基或式QC(=U)NRa的基团。
本发明的甚至更优选的式(I)化合物是这样一些化合物:其中Z1代表氨基基团或式QC(=U)NRa的基团。
当Z1代表式QC(=U)NRa的基团时,本发明的其它优选的式(I)化合物是其中U代表氧原子的那些。当Z1代表式QC(=U)NRa的基团时,本发明的其它优选的式(I)化合物是其中Ra代表氢原子、羟基基团、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C1-C8-烷氧基的那些。
当Z1代表式QC(=U)NRa的基团时,本发明的更优选的式(I)化合物是其中Ra代表氢原子的那些。当Z1代表式QC(=U)NRa的基团时,本发明的其它优选的式(I)化合物是这样一些化合物:其中Q代表经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C2-C8-炔基、经取代或未经取代的C1-C8-烷氧基、经取代或未经取代的C2-C8-烯氧基、经取代或未经取代的C2-C8-炔氧基、经取代或未经取代的C1-C8-烷基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的杂环基、经取代或未经取代的C3-C8-环烷氧基。
当Z1代表式QC(=U)NRa的基团时,本发明的更优选的式(I)化合物是这样一些化合物:其中Q代表经取代或未经取代的C4-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C4-C8-炔基、经取代或未经取代的C4-C8-烷氧基、经取代或未经取代的C4-C8-烯氧基、经取代或未经取代的C4-C8-炔氧基、经取代或未经取代的C3-C8-烷基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的杂环基。
当Z1代表式QC(=U)NRa的基团时,本发明的甚至更优选的式(I)化合物是这样一些化合物:其中Q代表经取代或未经取代的C4-C8-烷基、经取代或未经取代的C4-C8-炔基、经取代或未经取代的C4-C8-烷氧基、经取代或未经取代的C4-C8-烯氧基、经取代或未经取代的C4-C8-炔氧基、经取代或未经取代的芳基、经取代或未经取代的杂环基。当Z1代表式QC(=U)NRa的基团,并且Q代表经取代或未经取代的C4-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C4-C8-炔基、经取代或未经取代的C4-C8-烷氧基、经取代或未经取代的C4-C8-烯氧基、经取代或未经取代的C4-C8-炔氧基、经取代或未经取代的C3-C8-烷基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的杂环基时,本发明的其它优选的式(I)化合物是这样一些化合物:其中取代基选自卤素原子、氰基基团、(羟基亚氨基)-C1-C6-烷基基团、C1-C8-烷基、C3-C8-环烷基、C2-C8-烯基、C2-C8-炔基、C2-C8-烯氧基、C2-C8-炔氧基、C1-C8-烷氧基、C1-C8-烷基次磺酰基、(C1-C6-烷氧基亚氨基)-C1-C6-烷基、(C1-C6-烯氧基亚氨基)-C1-C6-烷基、(C1-C6-炔氧基亚氨基)-C1-C6-烷基、(苄氧基亚氨基)-C1-C6-烷基、C1-C8-烷氧基烷基、苄氧基、苄基次磺酰基、苯氧基、苯基次磺酰基、芳基基团或杂环基基团,或者其中取代基一起形成经取代或未经取代的、饱和或部分饱和的3-、4-、5-、6-、7-、8-、9-、10-或11-元环,所述环可以是碳环或包含至多4个杂原子的杂环,所述杂原子选自N、O和S。
当Z1代表式QC(=U)NRa的基团,并且Q代表经取代或未经取代的C4-C8-烷基、经取代或未经取代的C3-C8-环烷基、经取代或未经取代的C4-C8-炔基、经取代或未经取代的C4-C8-烷氧基、经取代或未经取代的C4-C8-烯氧基、经取代或未经取代的C4-C8-炔氧基、经取代或未经取代的C3-C8-烷基次磺酰基、经取代或未经取代的芳基、经取代或未经取代的杂环基时,本发明的更优选的式(I)化合物是这样一些化合物:其中取代基选自卤素原子、氰基基团、(羟基亚氨基)-C1-C6-烷基基团、C1-C8-烷基、C3-C8-环烷基、C2-C8-烯基、C2-C8-炔基、C2-C8-烯氧基、C2-C8-炔氧基、C1-C8-烷氧基、C1-C8-烷基次磺酰基、(苄氧基亚氨基)-C1-C6-烷基、C1-C8-烷氧基烷基、苄氧基、苯氧基、芳基基团或杂环基基团,或者其中取代基一起形成饱和或部分饱和的3-、4-、5-、6-元环,所述环可以是碳环或包含至多4个杂原子的杂环,所述杂原子选自N、O和S。
本发明的其它优选的式(I)化合物是其中Z2、Z3和Z4独立地代表氢原子、卤素原子、经取代或未经取代的C1-C8-烷基的那些。
本发明的更优选的式(I)化合物是其中Z2、Z3和Z4独立地代表氢原子的那些。
本发明的其它优选的式(I)化合物是这样一些化合物:其中Y1~Y5独立地代表氢原子、卤素原子、经取代或未经取代的C1-C8-烷基、经取代或未经取代的C3-C8-环烷基、具有1~5个卤素原子的经取代或未经取代的C1-C8-卤代烷基、经取代或未经取代的C1-C8-烷氧基。
本发明的更优选的式(I)化合物是这样一些化合物:其中Y1~Y5独立地代表氢原子、卤素原子、甲基、乙基、异丙基、异丁基、叔丁基、三氟甲基、二氟甲基、烯丙基、乙炔基、炔丙基、环丙基、甲氧基或三氟甲氧基。
本发明的甚至更优选的式(I)化合物是其中Y1~Y5独立地代表氢原子或氟原子的那些。关于本发明式(I)的化合物的取代基的上述优选方案可以以各种方式进行组合。这些优选特征的组合由此提供了本发明化合物的亚类。本发明优选的化合物的这些亚类的例子可具有以下组合特征:
·A的优选特征与X1、Y1~Y5和Z1~Z4的一种或多种的优选特征;
·X1的优选特征与A、Y1~Y5和Z1~Z4的一种或多种的优选特征;
·Y1的优选特征与A、X1、Y2~Y5和Z1~Z4的一种或多种的优选特征;
·Y2的优选特征与A、X1、Y1、Y3~Y5和Z1~Z4的一种或多种的优选特征;
·Y3的优选特征与A、X1、Y1、Y2、Y4、Y5和Z1~Z4的一种或多种的优选特征;
·Y4的优选特征与A、X1、Y1~Y3、Y5和Z1~Z4的一种或多种的优选特征;
·Y5的优选特征与A、X1、Y1~Y4和Z1~Z4的一种或多种的优选特征;
·Z1的优选特征与X1、Y1~Y5、A和Z2~Z4的一种或多种的优选特征;
·Z2的优选特征与X1、Y1~Y5、A、Z1和Z3~Z4的一种或多种的优选特征;
·Z3的优选特征与X1、Y1~Y5、A、Z4和Z1~Z2的一种或多种的优选特征;
·Z4的优选特征与X1、Y1~Y5、A和Z1~Z3的一种或多种的优选特征;
在本发明的化合物的取代基的优选特征的这些组合中,所述优选特征还可选自A、X1、Y1~Y5和Z1各自的更优选特征,从而形成本发明化合物的最优选亚类。
本发明还涉及用于制备式(I)化合物的方法,因此,本发明的另一方面提供从式(II)化合物制备式(I)化合物的方法P1:根据已知方法,可任选地在碱存在下,通过式(III)化合物的亲核取代反应产生式(IV)化合物;然后,根据已知方法可任选地在碱存在下,可任选地在酸存在下,对式(IV)化合物添加羟胺或羟胺盐以产生式(V)化合物;然后采用光气等效物,根据已知方法,可任选地在碱存在下,使式(V)化合物发生环化反应以产生式(Ia)化合物;然后采用式X1-LGa的烷基化剂,根据已知方法可任选地在碱存在下使式(Ia)化合物发生烷基化反应以产生式(I)化合物。在这种情况下,提供了本发明方法P1且所述方法P1可由如下反应方案说明:
方法P1
其中Y1、Y2、Y3、Y4、Y5、A和X1如本文定义,而LG和LGa独立地代表离去基团。合适的离去基团可选自下组:卤素原子或其它常规离核基团(例如三氟甲磺酸根、甲磺酸根或甲苯磺酸根)。
用于式(IV)化合物转换成式(V)化合物的合适的酸可选择为无机酸(例如氯化氢和硫酸),和有机酸(例如甲酸和乙酸)。
用于式(V)化合物转化成式(I)化合物的合适的光气等效物可选择为光气、双光气、三光气、羰基二咪唑、氯甲酸酯衍生物,例如氯甲酸乙酯和4-硝基苯氧基-氯甲酸酯。
式(II)和(III)化合物市售可得或是本领域技术人员容易取得的。制备的示例可在国际专利申请WO2009/130193中找到。式X1-LGa的化合物是市售可得的。
本发明还提供用于从式(Ib)化合物制备式(Ic)化合物的方法P2。
就本发明的式(Ib)化合物而言,如果Z1代表-NHRa,那么本发明的方法P1可通过进一步步骤完成,所述进一步步骤包括该基团的额外修饰,尤其是根据已知方法,通过酰化反应、烷氧基羰基化反应、烷基氨基羰基化反应、(硫)酰化反应、烷氧基(硫)羰基化反应、烷基次磺酰基(alkylsuphenyl)(硫)羰基化反应或烷基氨基(硫)羰基化反应进行修饰,以产生式(Ic)化合物。在这种情况下,提供本发明方法P2且所述方法P2可由如下反应方案说明:
方法P2
其中
Y1、Y2、Y3、Y4、Y5、X1、U、Ra和Q如本文定义,并且Ab代表A,其中Z1代表-NHRa;Ac代表A其中Z1代表式QC(=U)NRa的基团且LG’代表离去基团。
合适的离去基团可选自下组:卤素原子或其它常规离核基团(例如醇盐(alcoolate)、氢氧根或氰根)。
本发明还提供用于从式(Id)化合物制备式(Ie)化合物的方法P3:根据已知方法,可任选地在催化剂(尤其是过渡金属催化剂,例如钯盐或钯配合物诸如氯化钯(II)、乙酸钯(II)、四(三苯基膦)钯(0)、二氯化二-(三苯基膦)钯(II)、三(二亚苄基酮)二钯(0)、二(二亚苄基丙酮)钯(0)或1,1'-双(二苯基膦基)二茂铁]氯化钯(II))的存在下,通过亲和取代反应产生式(Ie)化合物。或者,根据已知方法,可任选地在碱(例如无机碱或有机碱)的存在下,通过向所述反应混合物分开添加钯盐和配合物配体以在所述反应混合物中直接生成所述钯配合物,所述配合物配体例如:膦,例如三乙基膦、三叔丁基膦、三环己基膦、2-(二环己基膦)联苯基、2-(二叔丁基膦)联苯基、2-(二环己基膦)-2'-(N,N-二甲基氨基)-联苯基、三苯基膦、三-(邻甲苯基)膦、3-(二苯基膦基)苯磺酸钠、三-2-(甲氧基苯基)膦、2,2'-双-(二苯基膦)-1,1'-联萘基、1,4-双-(二苯基膦)丁烷、1,2-双-(二苯基膦)乙烷、1,4-双-(二环己基膦)丁烷、1,2-双-(二环己基膦)乙烷、2-(二环己基膦)-2'-(N,N-二甲基氨基)-联苯基、双(二苯基膦基)二茂铁、三-(2,4-叔丁基苯基)-亚磷酸酯、(R)-(-)-1-[(S)-2-(二苯基膦基)二茂铁]乙基二叔丁基膦、(S)-(+)-1-[(R)-2-(二苯基膦基)二茂铁]乙基二环己基膦、(R)-(-)-1-[(S)-2-(二苯基膦基)二茂铁]乙基二环己基膦、(S)-(+)-1-[(R)-2-(二苯基膦基)二茂铁]乙基二叔丁基膦;所述碱优选碱土金属或碱金属氢化物、氢氧化物、酰胺、醇化物、乙酸盐、碳酸盐或碳酸氢盐,例如氢化钠、氨基钠、二异丙酰胺锂、甲醇钠、乙醇钠、叔丁醇钾、乙酸钠、乙酸钾、乙酸钙、氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠、碳酸铯或碳酸铵;以及叔胺,例如三甲胺、三乙胺(TEA)、三丁基胺、N,N-二甲苯胺、N,N-二甲基-苄胺、N,N-二异丙基-乙胺(DIPEA)、吡啶、N-甲基哌啶、N-甲基***啉、N,N-二甲基氨基吡啶、二氮杂双环辛烷(DABCO)、二氮杂二环壬烯(DBN)或二氮杂二环十一碳烯(DBU)。在这种情况下,提供本发明方法P3且所述方法P3可由如下反应方案说明:
方法P3
其中
·Y1、Y2、Y3、Y4、Y5和X1如本文定义,且Ad代表A(其中Z1代表卤素原子);Ae代表A(其中Z1代表氨基基团、氰基基团、经取代或未经取代的C1-C8-烷氧基氨基基团、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C3-C10-环烷基氨基、经取代或未经取代的C3-C10-环烯基氨基、经取代或未经取代的C5-C12-稠合的二环烷基氨基、经取代或未经取代的C5-C12-稠合的二环烯基氨基、经取代或未经取代的二-C1-C8-烷基氨基、经取代或未经取代的苯基氨基、经取代或未经取代的杂环基氨基或式QC(=O)NHRa的基团)。
本发明还提供用于从式(If)化合物制备式(Ig)化合物的方法P4。
就本发明的式(If)化合物而言,Af代表A(其中Z1代表式QC(=O)NRa的基团),本发明方法P1可通过进一步步骤完成,所述进一步步骤包括该基团的额外修饰,由其是根据已知方法在硫羰基化剂(例如,2,4-二(4-甲氧基苯基)-1,3,2,4-二硫杂二磷杂环丁烷(dithiadiphosphetane)2,4-二硫化物、五硫化磷、硫)的存在下通过硫羰基化反应来进行修饰,以产生式(Ig)化合物。在这种情况下,提供本发明方法P4且所述方法P4可由如下反应方案说明:
方法P4
其中
·Y1、Y2、Y3、Y4、Y5、X1、Ra和Q如本文定义;
·Af代表A,其中Z1代表式QC(=O)NRa的基团
·并且Ag代表A,其中Z1代表式QC(=S)NRa的基团。
本发明还涉及用于制备式(I)化合物的方法,因此,本发明的另一个方面提供用于从式(VI)化合物制备式(I)化合物的方法P5:在合适的氧化剂存在下使式(VI)化合物发生氧化反应以产生式(VII)化合物,然后根据已知方法,可任选地在微波辐射下,可任选地在脱水剂(例如分子筛)的存在下,通过式(VIII)化合物的缩合反应产生式(I)化合物。在这种情况下,提供本发明方法P5且所述方法P5可由如下反应方案说明:
方法P5
其中Y1、Y2、Y3、Y4、Y5、A和X1如本文定义。
在苯环和杂环之间的亚甲基位置发生氧化反应以产生氧代取代基的示例是已知的,并且可在如下文献中找到:Journal of the Chemical Society,Perkin Transactions1:Organic and Bio-Organic Chemistry(有机化学与生物有机化学)(1972-1999)(1982),(12),2995-3006。用于进行本发明方法P5的第一步骤的合适的氧化剂可以是无机和有机过氧化物(例如过氧化氢和过氧化苯甲酰)、金属和准金属氧化物(例如氧化锰(IV)、氧化铬(VI)、可任选地在单线态氧活化剂的存在下的氧、水性介质中的卤化剂(例如漂白剂)。
式(VI)化合物对本领域技术人员而言是容易取得的。制备的示例可在Annali diChimica(《化学史册》)(意大利罗马),(1963),53(10),1405-10中找到。
式(VIII)化合物与式(VIII)化合物的缩合反应的示例可在国际专利申请WO2010/000841中找到。
式(VIII)化合物对本领域技术人员而言是容易取得的。制备的示例可在国际专利申请WO2010/000841中找到。
本发明提供用于从式(Ih)化合物制备式(Ii)化合物的另一种方法P6,所述方法P6根据已知方法,通过烷基化反应进行。在这种情况下,提供本发明方法P6且所述方法P6可由如下反应方案说明:
方法P6
其中
·Y1、Y2、Y3、Y4、Y5、X1如本文定义。
·Ah代表A,其中Z1代表氨基、经取代或未经取代的C1-C8-烷基氨基或式-NHC(=O)Q的基团,其中Q如本文定义
·Ai代表A,其中Z1代表经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C3-C10-环烷基氨基、经取代或未经取代的C3-C10-环烯基氨基、经取代或未经取代的C5-C12-稠合的二环烷基氨基、经取代或未经取代的C5-C12-稠合的二环烯基氨基、经取代或未经取代的二-C1-C8-烷基氨基、经取代或未经取代的杂环基氨基或式QC(=U)NR的基团。
·R代表可任选经取代的C1-C8-烷基、C2-C8-烯基、C2-C8-炔基、C3-C10-环烷基、C3-C10-环烯基、C3-C10-稠合的二环烷基、C5-C12-稠合的二环烯基
·LG”代表离去基团。
合适的离去基团可选自下组:卤素原子或其它常规离核基团(例如醇盐(alcoolate)、氢氧根或氰根)。
本发明提供用于从式(Il)化合物制备式(Ik)化合物的另一种方法P7,所述方法P7根据已知方法,通过去保护反应来进行。在这种情况下,提供本发明方法P7且所述方法P7可由如下反应方案说明:
方法P7
其中
·Y1、Y2、Y3、Y4、Y5、X1如本文定义。
·Aj代表A,其中Z1代表式Z1 a-PG的基团,其中Z1 a代表经取代或未经取代的C1-C8-烷氧基氨基、经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的C2-C8-烯基氨基、经取代或未经取代的C2-C8-炔基氨基、经取代或未经取代的C3-C10-环烷基氨基、经取代或未经取代的C3-C10-环烯基氨基、经取代或未经取代的C5-C12-稠合的二环烷基氨基、经取代或未经取代的C5-C12-稠合的二环烯基氨基、经取代或未经取代的二-C1-C8-烷基氨基、经取代或未经取代的苯基氨基、经取代或未经取代的杂环基氨基,且PG代表保护基团,例如甲酰基基团、C1-C8-烷基羰基、C1-C8-烷氧基羰基、C1-C8-烷氧基-C1-C2-烷基、三(C1-C8-烷基)甲硅烷基-C1-C2-烷基、三(C1-C8-烷基)甲硅烷基氧基-C1-C2-烷基;
·Ak代表A,其中Z1代表Z1 a;
氨基保护基团及其相关的断裂方法是已知的,并可参见T.W.Greene和P.G.M.Wuts的《有机化学中的保护基团》(Protective Group in Organic Chemistry),第三版;约翰威立父子出版公司(John Wiley and Sons)。
本发明提供用于从式(Il)化合物制备式(Im)化合物的另一种方法P8,所述方法P8根据已知方法,在还原剂(例如氢气或氢化物衍生物,特别是氰基硼氢化钠)的存在下,通过氨基还原反应进行。在这种情况下,提供本发明方法P8且所述方法P8可由如下反应方案说明:
方法P8
其中
·Y1、Y2、Y3、Y4、Y5、X1如本文定义;
·Al代表A,其中Z1代表氨基基团、经取代或未经取代的C1-C8-烷基氨基;
·Am代表A,其中Z1代表经取代或未经取代的C1-C8-烷基氨基、经取代或未经取代的二-C1-C8-烷基氨基。
本发明提供用于从式(In)化合物制备式(Io)化合物的另一种方法P9,所述方法根据如下反应方案以一步或两步进行。
方法P9
其中
Y1、Y2、Y3、Y4、Y5、X1、Ra和Q如本文定义,并且Ab代表A,其中Z1代表-NHRa;Ac代表A其中Z1代表式QC(=U)NRa的基团且LG’代表离去基团。
其中
·Y1、Y2、Y3、Y4、Y5、X1、Ra如本文定义;
·An代表A,其中Z1代表-NHRa;
·Ao代表A,其中Z1代表Q’C(=O)NRa,其中Q’代表经取代或未经取代的C1-C8-烷氧基、经取代或未经取代的C2-C8-烯氧基、经取代或未经取代的C2-C8-炔氧基、经取代或未经取代的C1-C8-烷基次磺酰基、经取代或未经取代的C2-C8-烯基次磺酰基、经取代或未经取代的C2-C8-炔基次磺酰基、经取代或未经取代的芳基次磺酰基、经取代或未经取代的环烷氧基;经取代或未经取代的环烯氧基、经取代或未经取代的芳氧基;经取代或未经取代的杂环基氧基、经取代或未经取代的C5-C12-稠合的二环烷氧基、经取代或未经取代的C5-C12-稠合的二环烯氧基、经取代或未经取代的C5-C12-苯并稠合的碳环基氧基、经取代或未经取代的C5-C12-苯并稠合的杂环基氧基;●LG1和LG2代表离去基团●合适的离去基团可选自下组:卤素原子或其它常规的离核基团,例如咪唑、卤代苯酚盐等。
根据本发明,方法P1~P9可在(合适时)溶剂存在下和(合适时)碱存在下实施。
根据本发明,方法P1和P2(合适时)可在催化剂存在下实施。合适的催化剂可选自4-二甲基-氨基吡啶、1-羟基-苯并***或二甲基甲酰胺。
在LG’代表羟基的情况下,本发明方法P2可在缩合剂存在下实施。合适的缩合剂可选自下组:酰卤形成剂,例如光气、三溴化磷、三氯化磷、五氯化磷、氧化三氯化磷或亚磺酰氯;酐形成剂,例如氯甲酸乙酯、氯甲酸甲酯、氯甲酸异丙酯、氯甲酸异丁酯或甲磺酰氯;碳二亚胺,例如N,N'-二环已基碳二亚胺(DCC);或其它常规缩合剂,例如五氧化二磷、多磷酸、N,N'-羰基-二咪唑、2-乙氧基-N-乙氧基羰基-1,2-二氢喹啉(EEDQ)、三苯基膦/四氯甲烷、水合氯化4-(4,6-二甲氧基[1.3.5]三嗪-2-基)-4-甲基吗啉鎓或六氟磷酸三吡咯烷基(tripyrrolidino)溴化鏻-盐。
用于实施本发明方法P1~P9的合适溶剂是常用的惰性有机溶剂。优选使用可任选卤代的脂族、脂环族或芳族烃类,例如石油醚、己烷、庚烷、环己烷、甲基环己烷、苯、甲苯、二甲苯或萘烷;氯苯、二氯苯、二氯甲烷、氯仿、四氯化碳、二氯乙烷或三氯乙烷;醚类,例如***、二异丙醚、甲基叔丁基醚、甲基叔戊基醚、二噁烷、四氢呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷或茴香醚;腈类,例如乙腈、丙腈、正丁腈或异丁腈或苄腈;酰胺类,例如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮、或六甲基磷酰三胺;酯类,例如乙酸甲酯或乙酸乙酯;亚砜类,例如二甲亚砜,或砜类,例如环丁砜。
用于实施本发明方法P1~P9的合适的碱是常用于此类反应的无机碱和有机碱。优选使用碱土金属、碱金属氢化物,碱金属氢氧化物或碱金属醇盐,例如氢氧化钠、氢化钠、氢氧化钙、氢氧化钾、叔丁醇钾或其它氢氧化铵;碱金属碳酸盐,例如碳酸钠、碳酸钾、碳酸氢钾、碳酸氢钠、碳酸铯;碱金属或碱土金属乙酸盐,例如乙酸钠、乙酸钾、乙酸钙;以及叔胺类,例如三甲胺、三乙胺、二异丙基乙胺、三丁胺、N,N-二甲基苯胺、吡啶、N-甲基哌啶、N,N-二甲基氨基吡啶、1,4-二氮杂双环[2.2.2]辛烷(DABCO)、1,5-二氮杂双环[4.3.0]壬-5-烯(DBN)或1,8-二氮杂双环[5.4.0]十一碳-7-烯(DBU)。
当实施本发明的方法P1~P9时,反应温度可在相对宽的范围内独立地变化。本发明方法P1通常在-20℃~160℃的温度下实施。
本发明方法P1~P9通常在大气压下独立地实施。然而,也可在升压或减压下操作。
通过常用方法来实施后处理(Work-up)。通常用水处理反应混合物,并分离出有机相,干燥后在减压下浓缩。合适时,通过惯常方法(如色谱法或重结晶法)去除残留的残余物中任何可能仍存在的杂质。
本发明的化合物可按照上述方法制备。但应理解,本领域技术人员基于其一般知识以及可获得的出版物,能够根据所需合成的本发明的各种具体化合物对本发明方法进行相应调整。
式(IV)化合物可按照WO2011/080254中所述的方法方便地制备,所述文献通过引用纳入本文。在另一方面中,若A如本文定义,那么本发明涉及可作为中间体化合物或物质用于本发明所述制备方法的式(V)化合物。
因此,本发明提供式(V)化合物,其中Y1、Y2、Y3、Y4、Y5和A如本文定义。
在另一个方面中,若X1代表经取代或未经取代的C1-C8-烷基,那么本发明涉及可作为中间体化合物或物质用于本发明所述制备方法的式(VII)化合物。
因此,本发明提供式(VII)化合物,其中Y1、Y2、Y3、Y4、Y5如本文定义,并且X1代表经取代或未经取代的C1-C8-烷基。
在另一方面,本发明还涉及含有有效且非植物毒性量的通式(I)的活性化合物的杀真菌剂组合物。
术语“有效且非植物毒性量”是指本发明组合物的一定量,所述量足以控制或者破坏存在的或易于在农作物上出现的真菌,且不会使所述农作物产生任何明显的植物毒性症状。该量根据以下因素可在很宽的范围内变化:待控制的真菌、作物类型、气候条件和包含在本发明的杀真菌组合物中的化合物。这个量可通过***性田间试验来确定,这是在本领域技术人员能力范围之内的。
因此,本发明提供一种杀真菌剂组合物,该组合物包含:有效量的如本文定义的式(I)化合物(作为活性成分),以及农业上可接受的担体(support)、载体或填料(filler)。
根据本发明,术语“担体”表示天然或合成的有机或无机化合物,其与式(I)活性化合物组合或联合以使得该活性化合物更易于被施用至植物,尤其是植物的各个部分。因此,该担体通常是惰性的,并且应是农业上可接受的。所述担体可以是固体或液体。合适的担体的示例包括粘土、天然或合成的硅酸盐、二氧化硅、树脂、蜡、固体肥料、水、醇类(特别是丁醇)、有机溶剂、矿物油和植物油及其衍生物。也可以使用此类担体的混合物。
本发明的组合物还可以包含其它组分。具体地,所述组合物还可包含表面活性剂。所述表面活性剂可以是离子型或非离子型的乳化剂、分散剂或润湿剂、或这些表面活性剂的混合物。例如,聚丙烯酸盐、木质素磺酸盐、苯酚磺酸盐或萘磺酸盐、环氧乙烷与脂肪醇或脂肪酸或脂肪胺的缩聚物、取代的苯酚(特别是烷基苯酚或芳基苯酚)、磺基琥珀酸酯的盐、牛磺酸衍生物(特别是牛磺酸烷基酯(alkyl taurate))、聚氧乙基化醇或苯酚的磷酸酯、多元醇的脂肪酸酯,以及含有硫酸、磺酸和磷酸官能团的上述化合物的衍生物。当活性化合物和/或惰性担体不溶于水且所施用的媒介试剂是水时,通常必需存在至少一种表面活性剂。优选地,以组合物的重量计,表面活性剂的含量可为5~40%。
任选地,还可包括其它组分,例如,保护性胶体、粘合剂、增稠剂、触变剂、渗透剂、稳定剂、螯合剂。更一般而言,可使所述活性化合物与符合常用配制技术的任何固体或液体添加剂组合。
本发明的组合物通常可包含0.05~99重量%的活性化合物,优选为10~70重量%。
本发明的组合物可以各种形式使用并且可用于各种制剂,例如气雾分散剂、胶囊悬浮剂(capsule suspension)、冷雾浓缩剂、可撒粉剂、可乳化的浓缩剂、水包油乳液、油包水乳液、包胶粒剂、细颗粒剂、用于种子处理的可流动浓缩剂、气体(压力下)制剂、气体发生剂、颗粒剂、热雾浓缩剂、大粒剂、微粒剂、油可分散性粉剂、油混溶性可流动浓缩剂、油混溶性液体、糊剂、植物小棒、用于干种处理的粉剂、农药包衣的种子、可溶性浓缩剂、可溶性粉剂、用于种子处理的溶液、悬浮浓缩剂(可流动的浓缩剂)、超低容量(ULV)液体、超低容量(ULV)悬浮剂、水可分散粒剂或片剂、用于浆液处理的水可分散粉剂、水溶性粒剂或片剂、用于种子处理的水溶性粉剂、以及可润湿性粉剂。这些组合物不仅包括待用合适的设备(例如喷雾器或撒粉设备)施用至待处理的植物或种子上的组合物,而且包括在施用于农作物之前必须进行稀释的经浓缩的市售组合物。
本发明的化合物还可与一种或多种以下物质混合:杀昆虫剂、杀真菌剂、杀细菌剂、引诱剂、杀螨剂或信息素活性物质或者有生物活性的其它化合物。由此获得的混合物的活性谱更广。与其它杀真菌剂化合物的混合物尤其有益。包含式(I)化合物与杀细菌剂化合物的混合物的本发明组合物也尤其有益。
所述制剂可通过原本已知的方式制备,例如通过将所述活性成分与至少一种以下常规物质混合来制备:填充剂、溶剂或稀释剂、佐剂、乳化剂、分散剂和/或粘结剂或固定剂、湿润剂、防水剂、(合适时)干燥剂和紫外稳定剂,以及(合适时)染料和颜料、消泡剂、防腐剂、无机和有机增稠剂、粘合剂、赤霉素以及其它加工助剂和水。根据待制备的制剂类型,需要其它加工步骤,例如湿法研磨、干法研磨和制粒。
本发明的活性成分可以本身的形式存在,或者以其(市售)制剂形式以及由这些制剂所制备的使用形式存在,所述制剂是本发明活性成分与以下其它(已知)活性成分的混合物的形式:例如杀昆虫剂、引诱剂、消毒剂、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、安全剂和/或化学信息素。
本发明还涉及如本文定义的式(I)化合物用于防控病原性真菌的应用。
本发明还涉及如本文定义的式(I)化合物用于处理转基因植物的应用。
本发明还涉及如本文定义的式(I)化合物用于处理种子和转基因植物的种子的应用。
本发明还涉及制造用于防控植物病原性有害真菌的组合物的方法,其特征在于,使如本文定义的式(I)化合物的衍生物与填充剂和/或表面活性剂混合。
本发明的另一个目的是,提供一种控制植物、作物或种子的植物病原真菌的方法,其特征在于,将农业上有效且基本上非植物毒性量的本发明的农药组合物以种子处理、叶部施加、茎部施加、浸透或滴灌施加(化学施加)的方式施用于以下部分:种子、植物或植物果实,或已种植或打算种植植物的土壤或惰性基质(例如无机基质,如砂、石棉、玻璃棉;膨胀矿物质,例如珍珠岩、蛭石、沸石或膨胀粘土)、浮石、火成碎屑物质或材料、合成的有机基质(例如聚氨酯)、有机基质(例如泥炭、堆肥、树木废产物(例如椰壳、木纤维或木屑、树皮))或液体基质(例如浮动水培***、营养液膜技术、气栽体系)。
术语“施用于待处理的植物”应理解为是指出于本发明的目的,可通过如下的各种处理方法施用作为本发明主题的农药组合物:
·向所述植物的地上部分喷涂包含所述组合物之一的液体;
·在所述植物周围采用喷粉、向土壤中掺入颗粒或粉末、喷雾方式,而在所述植物是树木的情况下采用注射或涂抹方式;
·借助包含所述组合物之一的植物保护混合物,对所述植物的种子进行涂覆或膜涂覆。
本发明方法可以是治愈、预防或根除的方法。
在该方法中,所用组合物可预先通过使两种或更多种本发明活性化合物混合来制备。
根据此方法的一种替代性方式,也可同时、连续或分开施用化合物(A)和(B),以产生各包含两种或三种活性成分(A)或(B)中之一的不同组合物的结合(A)/(B)效果。
本发明处理方法中常施用的活性化合物的剂量通常且适宜为:
·对于叶部处理:0.1~10,000g/ha(克/公顷),优选10~1,000g/ha,更优选50~300g/ha;在浸透或滴灌施用的情况下,所述剂量甚至可减少,尤其是当使用惰性基质(例如石棉或珍珠岩)时;
·对于种子处理:2~200g/100kg种子,优选3~150g/100kg种子;
·对于土壤处理:0.1~10,000g/ha,优选1~5,000g/ha。
本文所示的剂量是作为本发明方法的说明性示例给出。本领域技术人员知道如何根据待处理植物或作物的性质调节施用剂量。
在具体条件下,例如根据待处理或控制的植物致病真菌的性质,较低剂量可提供足够的保护。某些气候条件、抗性或其它因素(例如植物致病真菌的性质或(例如)植物受该真菌感染的程度)可需要更高剂量的组合活性成分。最佳剂量通常取决于各种因素,例如待处理的植物致病真菌的类型,受感染植物的类型或发展程度,植被密度或者施用方法。
用本发明的农药组合物或组合处理的作物是例如但不限于,例如葡萄树,也可为谷物、蔬菜、苜蓿、大豆、市售花园作物、草皮、树木或园艺植物。
本发明的处理方法还可用于处理繁殖材料(如块茎或根茎等),以及种子、幼苗或移植幼苗以及植物或移植植物。该处理方法也可用于处理根。本发明的处理方法也可用于处理植物的地上部分,例如有关植物的树干、茎或梗、叶、花和果实。
在可通过本发明方法保护的植物中可包括棉花、亚麻、藤本植物、水果或蔬菜作物,例如蔷薇科(Rosaceae sp.)(例如,仁果类水果,如苹果和梨,还有核果,诸如杏、杏仁和桃子)、茶蔗子科(Ribesioidae sp.)、胡桃科(Juglandaceae sp.)、桦木科(Betulaceaesp.)、漆树科(Anacardiaceae sp.)、山毛榉科(Fagaceae sp.)、桑科(Moraceae sp.)、木犀科(Oleaceae sp.)、猕猴桃科(Actinidaceae sp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和粉芭蕉(plantins))、茜草科(Rubiaceae sp.)、山茶科(Theaceae sp.)、梧桐科(Sterculiceae sp.)、芸香科(Rutaceae sp.)(例如柠檬、橙子和葡萄柚);茄科(Solanaceae sp.)(例如,西红柿)、百合科(Liliaceae sp.)、紫菀科(Asteraceae sp.)(例如莴苣)、伞形科(Umbelliferae sp.)、十字花科(Cruciferae sp.)、藜科(Chenopodiaceae sp.)、葫芦科(Cucurbitaceae sp.)、蝶形花科(Papilionaceaesp.)(例如豌豆)、蔷薇科(Rosaceae sp.)(例如草莓);主要作物,诸如禾本科(Graminaesp.)(例如玉米、菌苔或谷物如小麦、稻、大麦和黑小麦)、紫菀科(Asteraceae sp.)(例如向日葵)、十字花科(Cruciferae sp.)(例如油菜)、豆科(Fabacae sp.)(例如花生)、蝶形花科(Papilionaceae sp.)(例如大豆)、茄科(Solanaceae sp.)(例如马铃薯)、藜科(Chenopodiaceae sp.)(例如甜菜根);园艺作物和森林作物;以及这些作物的遗传改进的同系物。
本发明的处理方法可用于处理经遗传改进的有机体(GMOs),例如植物或种子。经遗传改进的植物(或转基因植物)是其中异源基因已经稳定地整合入基因组中的植物。术语“异源基因”主要是指如下基因:其在植物外部被提供或组装,而当被引入细胞核、叶绿体或线粒体基因组中时,通过表达感兴趣的蛋白质或多肽或通过使所述植物中存在的其它一种或多种基因下调或沉默(使用例如反义技术、共抑制技术或RNA干扰-RNAi-技术)来赋予该经转化的植物新的或改进的农艺性质或其它性质。位于基因组中的异源基因也称作转基因。由植物基因组中的特定位置定义的转基因称作转化或转基因事件。
根据植物物种或植物品种、其位置和生长条件(土壤、气候、生长期、营养),本发明的处理还可产生超叠加(“协同”)效果。因此,例如,使根据本发明可用的活性化合物和组合物的施用比率减小和/或活性范围拓宽和/或活性增加,则使植物生长得更好,对于高温或低温的耐受性增加,对于干旱或水或土壤含盐量的耐受性提高,开花性能提高,收获更容易,成熟加速,收获产量更高,果实更大,植物高度更高,叶子颜色更绿,开花更早,收获的产物的品质更高和/或营养价值更高,果实中的糖浓度更高、收获的产物的贮存稳定性和/或加工性能更好,这些皆有可能,并超过实际预期的效果。
在某些施用比率下,本发明的活性化合物复配物还可在植物中具有强化效果。因此,其还可适用于调动植物防御***抵抗不希望的植物致病真菌和/或微生物和/或病毒的攻击。这可能(合适时)是本发明组合的活性增强(例如抵抗真菌)的原因之一。在本文中,植物强化(抗性诱导)物质在本文中应理解为是指如下的物质或物质组合:所述物质或物质组合能够刺激植物的防御***,从而当之后接种不需要的植物病原性真菌和/或微生物和/或病毒时,所述经处理的植物针对这些不需要的植物病原性真菌和/或微生物和/或病毒显示很大程度的抗性。在本文中,不需要的植物病原性真菌和/或微生物和/或病毒应理解为是指植物病原性真菌、细菌和病毒。因此,本发明的物质可用于保护植物,使其在经过所述处理后的一段时间内能抵抗上述病原体的攻击。在使用所述活性化合物处理植物之后,保护起作用的时间通常为1~10天,优选为1~7天。
本发明的优选待处理的植物和植物品种包括拥有使这些植物具有特别有利、有用性状的遗传材料(无论通过育种和/或生物技术方式获得)的所有植物。
本发明的优处理的植物和植物品种对一种或多种生物胁迫具有抗性,即所述植物对如下的动物和微生物虫害显示出较好的防御,例如线虫、昆虫、螨虫、植物病原性真菌、细菌、病毒和/或类病毒。
本发明的待处理的植物和植物品种还可以是对一种或多种非生物胁迫具有抗性的植物。非生物胁迫条件可包括,例如,干旱、冷温暴露、热暴露、渗透胁迫、水淹、土壤盐度增加、矿物质暴露增加、臭氧暴露、强光暴露、限制性供应氮营养素、限制性供应磷营养素、避阴。
本发明的待处理的植物和植物品种还可以是特点为产量增加的植物。所述植物产量增加可由以下原因导致,例如,经改善的植物生理学、生长和发育(例如水利用效率、水保留效率)、经改善的氮利用、增强的碳同化、经改善的光合作用、提高的发芽效率和加速成熟。产量还可受经改善的植物结构(在胁迫和非胁迫条件下)影响,其包括但不限于,提早开花、对杂交种子生产的开花控制,幼苗活力、植物大小、节间数量及距离、根生长、种子大小、果实大小、豆荚大小、豆荚或穗数量、每穗或豆荚的种子数量、种子质量(seed mass)、提高种子填充、减少种子分散、减少豆荚开裂和耐倒伏性。其它产量特性包括种子成分,例如碳水化合物含量、蛋白质含量、油含量及成分、营养价值、抗营养化合物的减少、经改善的加工性和更好的贮备稳定性。
本发明可处理的植物是已经表达出杂种优势或杂交活力特征,导致具有更高产量、活力、健康和对生物和非生物胁迫的抗性的杂交植物。此类植物通常通过近交雄性不育亲本(雌性亲本)与另一近交雄性可育亲本(雄性亲本)杂交获得。杂交种子通常从雄性不育植物收获并出售给种植者。雄性不育植物有时可(例如在玉米中)通过去除雄性产生,即机械去除雄性生殖器官(或雄花),但更通常地,雄性不育是由植物基因组中的遗传决定簇产生。在这种情况下,以及特别是当种子是从杂交植物收获的所需产物时,其通常用于确保杂交植物中的雄性能育性得以完全恢复。这可通过确保雄性亲本具有合适的能育性恢复基因来实现,所述能育性恢复基因能够恢复包含造成雄性不育的遗传决定簇的杂交植物中的雄性能育性。雄性不育的遗传决定簇可位于细胞质中。例如,对于芸苔属物种中细胞质的雄性不育(CMS)的例子已有描述(WO 1992/005251、WO 1995/009910、WO 1998/27806、WO 2005/002324、WO 2006/021972和US 6,229,072)。然而,雄性不育的遗传决定簇也可位于细胞核基因组中。雄性不育植物也可由植物生物技术方法(例如基因工程)获得。WO 1989/10396中描述了获得雄性不育植物的特别有用的方法,其中,例如核糖核酸酶(例如芽孢杆菌RNA酶)在雄蕊的绒毡层细胞中选择性地表达。然后可通过在绒毡层细胞中表达核糖核酸酶抑制剂(例如芽胞杆菌RNA酶抑制剂)来恢复能育性(例如WO 1991/002069)。
本发明可处理的植物或植物品种(由植物生物技术方法获得,例如通过基因工程获得)是除草剂耐受植物,即对一种或多种给定的除草剂具有耐受性的植物。这些植物可通过遗传转化获得,或通过选择包含赋予这种除草剂耐受性的突变的植物获得。
耐除草剂植物是例如耐草甘膦植物,即对除草剂草甘膦或其盐具有耐受性的植物。可通过不同的方法使植物对草甘膦具有耐受性。例如,草甘膦耐受性植物可通过用具有编码5-烯醇丙酮酰莽草酸-3-磷酸合酶(EPSPS)的基因对植物进行转化来获得。这些EPSPS基因的例子是鼠伤寒沙门菌(Salmonella typhimurium)的AroA基因(突变CT7)(Comai等,科学(Science)(1983),221,370-371)、农杆菌(Agrobacterium sp.)的CP4基因(Barry等,Curr.Topics Plant Physiol.(1992),7,139-145)、编码牵牛花EPSPS的基因(Shah等,科学(Science)(1986),233,478-481)、编码番茄EPSPS的基因(Gasser等,J.Biol.Chem.(1988),263,4280-4289)、或编码牛筋草(Eleusine)EPSPS的基因(WO 2001/66704)。还可以是突变的EPSPS,如例如EP-A 0837944、WO 2000/066746、WO 2000/066747或WO 2002/026995中所述。草甘膦耐受性植物还可通过表达编码草甘膦氧化还原酶的基因来获得,如US 5,776,760和US 5,463,175中所述。草甘膦耐受性植物还可通过表达编码草甘膦乙酰基转移酶的基因来获得,如例如WO 2002/036782、WO 2003/092360、WO 2005/012515和WO 2007/024782中所述。草甘膦耐受性植物还可通过选择包含天然产生的上述基因突变体的植物来获得,如例如WO 2001/024615或WO 2003/013226中所述。
其它除草剂耐受性植物是例如对抑制酶谷氨酰胺合成酶的除草剂(例如双丙氨磷、草胺膦或草丁膦)具有耐受性的植物。这些植物可通过表达解除所述除草剂的毒性或抵抗抑制的突变谷氨酰胺合成酶来获得。一种此类有效的解毒酶是一种编码草胺膦乙酰基转移酶的酶(例如链霉菌属(Streptomyces)物种的bar或pat蛋白)。例如,US 5,561,236、US5,648,477、US 5,646,024、US 5,273,894、US 5,637,489、US 5,276,268、US 5,739,082、US5,908,810和US 7,112,665中描述了表达外源草胺膦乙酰基转移酶的植物。
其它除草剂耐受性植物还有对抑制羟基苯基丙酮酸双氧化酶(HPPD)的除草剂具有耐受性的植物。羟基苯基丙酮酸双氧化酶是催化使对-羟基苯丙酮酸(HPP)转化成尿黑酸盐的反应的酶。对HPPD-抑制剂具有耐受性的植物可采用编码天然产生的抗HPPD酶的基因,或编码突变HPPD酶的基因来转化,如WO 1996/038567、WO 1999/024585和WO 1999/024586中所述。对HPPD-抑制剂的耐受性还可通过用编码某些能够形成尿黑酸盐的酶的基因转化植物来获得,尽管HPPD-抑制剂可抑制天然HPPD酶。此类植物和基因在WO 1999/034008和WO2002/36787中有描述。植物对于HPPD-抑制剂的耐受性还可通过使用编码酶预苯酸盐脱氢酶的基因(除了使用编码HPPD耐受性酶的基因外)转化植物来提高,如WO 2004/024928中所述。
对除草剂具有抗性的其它植物是对乙酰乳酸合酶(ALS)抑制剂具有耐受性的植物。已知ALS抑制剂包括,例如磺酰脲、咪唑并啉酮、***并嘧啶、嘧啶氧基(硫基)苯甲酸酯/盐、和/或磺酰基氨基羰基***啉酮除草剂。已知ALS酶(也称作乙酰羟基酸合酶,AHAS)中不同突变会提供对于不同除草剂和除草剂基团的耐受性,如例如Tranel和Wright,WeedScience(2002),50,700-712,以及US 5,605,011、US 5,378,824、US 5,141,870和US 5,013,659中所述。磺酰脲耐受性植物和咪唑并啉酮耐受性植物的生产如US 5,605,011、US5,013,659、US 5,141,870、US 5,767,361、US 5,731,180、US 5,304,732、US 4,761,373、US5,331,107、US 5,928,937和US 5,378,824、以及国际公开WO 1996/033270中所述。其它咪唑并啉酮耐受性植物还描述于例如WO 2004/040012、WO 2004/106529、WO 2005/020673、WO2005/093093、WO 2006/007373、WO 2006/015376、WO 2006/024351和WO 2006/060634中。其它磺酰脲耐受性植物和咪唑并啉酮耐受性植物还如(例如)WO 2007/024782中所述。
其它咪唑并啉酮和/或磺酰脲耐受性植物可通过诱导突变、在存在除草剂的情况下选择细胞培养物或突变育种来获得,如(例如)US 5,084,082(对于大豆)、WO 1997/41218(对于水稻)、US 5,773,702和WO 1999/057965(对于甜菜)、US 5,198,599(对于莴苣)、或WO2001/065922(对于向日葵)中所述。
本发明还可处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)是昆虫抗性转基因植物,即抵抗某些目标昆虫的攻击的植物。这些植物可通过遗传转化,或通过选择包含赋予该昆虫抗性的突变的植物来获得。
本文中所用的“昆虫抗性转基因植物”包括含有至少一种转基因的任何植物,所述转基因包含编码如下物质的编码序列:
1)来自苏云金芽孢杆菌(Bacillus thuringiensis)的杀虫晶体蛋白或其杀虫蛋白,例如Crickmore等人,Microbiology and Molecular Biology Reviews(1998),62,807-813,由Crickmore等人(2005)在苏云金芽孢杆菌毒素命名法中更新,网址为http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/)中所列的杀虫晶体蛋白,或其杀虫部分,例如Cry蛋白类Cry1Ab、Cry1Ac、Cry1F、Cry2Ab、Cry3Aa、或Cry3Bb的蛋白质或其杀虫部分;或
2)在存在来自苏云金芽孢杆菌(Bacillus thuringiensis)的第二其它晶体蛋白或其部分的情况下,杀虫的来自苏云金芽孢杆菌(Bacillus thuringiensis)的晶体蛋白或其部分,例如由Cry34和Cry35晶体蛋白组成的二元毒素(Moellenbeck等人,Nat.Biotechnol.(2001),19,668-72;Schnepf等人,Applied Environm.Microbiol.(2006),71,1765-1774);或
3)包含来自苏云金芽孢杆菌(Bacillus thuringiensis)的不同杀虫晶体蛋白部分的杂交杀虫蛋白,例如上述1)的蛋白的杂交体或上述2)的蛋白的杂交体,例如由玉米事件MON98034产生的Cry1A.105蛋白(WO 2007/027777);或
4)上述1)~3)中的任何一种蛋白质,其中一些(优选1~10种)氨基酸被另一种氨基酸代替以获得对目标昆虫物种的更高杀虫活性,和/或扩展受影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中在编码DNA中引入的变化,例如玉米事件MON863或MON88017中的Cry3Bb1蛋白,或玉米事件MIR604中的Cry3A蛋白;
5)来自苏云金芽孢杆菌(Bacillus thuringiensis)或蜡样芽胞杆菌(Bacilluscereus)的杀虫分泌蛋白,或其杀虫部分,例如在http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html中所列的营养期杀虫(VIP)蛋白,例如来自VIP3Aa蛋白类的蛋白;或
6)来自苏云金芽孢杆菌或蜡样芽孢杆菌的分泌蛋白,该蛋白在来自苏云金芽孢杆菌或蜡样芽孢杆菌的第二分泌蛋白存在下具有杀虫性,例如由VIP1A和VIP2A蛋白组成的二元毒素(WO 1994/21795);或
7)包含来自苏云金芽孢杆菌或蜡样芽胞杆菌的不同分泌蛋白部分的杂交杀虫蛋白,例如上述1)中蛋白的杂交体或上述2)中蛋白的杂交体;或
8)上述1)~3)中的任何一种蛋白质,其中一些(较好为1-10)氨基酸被另一种氨基酸代替以获得对目标昆虫物种的更高杀虫活性,和/或扩展受影响的目标昆虫物种的范围,和/或由于在克隆或转化过程中在编码DNA中引入的变化(同时仍编码杀虫蛋白),例如玉米事件COT102中的VIP3Aa蛋白。
当然,本文中所用的昆虫抗性转基因植物,还包括包含编码上述1~8类中任一种蛋白质的基因的组合的任何植物。在一种实施方式中,昆虫抗性植物包含一种以上编码上述1~8类中的任一种蛋白质的转基因,从而在使用针对不同目标昆虫物种的不同蛋白质时扩展受影响的目标昆虫物种的范围,或通过使用对相同目标昆虫物种具有杀虫性但具有不同作用模式(例如在昆虫中结合不同的受体结合位点)的不同蛋白质来延迟植物的昆虫抗性发展。
本发明还可处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)可耐受非生物胁迫。此类植物可通过遗传转化,或通过选择包含赋予该胁迫抗性的突变的植物来获得。特别有用的胁迫耐受性植物包括:
a.包含能够减少植物细胞或植物中多聚(ADP-核糖)聚合酶(PARP)基因的表达和/或活性的转基因的植物,如WO 2000/004173或WO2006/045633或PCT/EP07/004142中所述。
b.包含使能够减少植物或植物细胞的PARG编码基因的表达和/或活性的转基因增强的胁迫耐受性的植物,如(例如)WO 2004/090140中所述。
c.包含可增强烟酰胺腺嘌呤二核苷酸补救合成途径的植物功能化酶的转基因编码的胁迫耐受性的植物,所述植物功能化酶包括烟酰胺酶、烟酸磷酸核糖基转移酶、烟酸单核苷酸腺嘌呤转移酶、烟酰胺腺嘌呤二核苷酸合成酶或烟碱酰胺磷酸核糖基转移酶,如(例如)WO2006/032469或WO 2006/133827或PCT/EP07/002433中所述。
本发明还可处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)显示出改变了所收获的产品的数量、品质和/或储存稳定性,和/或改变了所收获的产品的具体成分的性质,例如:
1)合成改性的淀粉的转基因植物,其物理化学性质,尤其是直链淀粉含量或直链淀粉/支链淀粉比、支化程度、平均链长、侧链分布、粘度行为、胶凝强度、淀粉颗粒尺寸和/或淀粉颗粒形貌,与野生型植物细胞或植物中的合成淀粉相比有所改变,从而其更适合于具体的应用。所述合成改性淀粉的转基因植物在以下文献中公开:例如EP 0571427、WO1995/004826、EP 0719338、WO 1996/15248、WO 1996/19581、WO 1996/27674、WO 1997/11188、WO 1997/26362、WO 1997/32985、WO 1997/42328、WO 1997/44472、WO 1997/45545、WO 1998/27212、WO 1998/40503、WO99/58688、WO 1999/58690、WO 1999/58654、WO 2000/008184、WO 2000/008185、WO 2000/008175、WO 2000/28052、WO 2000/77229、WO 2001/12782、WO 2001/12826、WO 2002/101059、WO 2003/071860、WO 2004/056999、WO 2005/030942、WO 2005/030941、WO 2005/095632、WO 2005/095617、WO 2005/095619、WO 2005/095618、WO 2005/123927、WO 2006/018319、WO 2006/103107、WO 2006/108702、WO 2007/009823、WO 2000/22140、WO 2006/063862、WO 2006/072603、WO 2002/034923、EP06090134.5、EP 06090228.5、EP 06090227.7、EP 07090007.1、EP 07090009.7、WO 2001/14569、WO 2002/79410、WO 2003/33540、WO 2004/078983、WO 2001/19975、WO 1995/26407、WO 1996/34968、WO 1998/20145、WO 1999/12950、WO 1999/66050、WO 1999/53072、US 6,734,341、WO 2000/11192、WO 1998/22604、WO 1998/32326、WO 2001/98509、WO 2001/98509、WO 2005/002359、US 5,824,790、US 6,013,861、WO 1994/004693、WO 1994/009144、WO 1994/11520、WO 1995/35026、WO 1997/20936。
2)合成非淀粉碳水化合物聚合物的转基因植物,或与未经过遗传修饰的野生型植物相比具有改变的性质的合成非淀粉碳水化合物聚合物的转基因植物。示例有:产生多聚果糖(尤其是菊糖和果聚糖类型)的植物(EP 0663956、WO 1996/001904、WO 1996/021023、WO 1998/039460、及WO 1999/024593中所揭示);产生α-1,4-葡聚糖的植物(如WO 1995/031553、US 2002/031826、US 6,284,479、US 5,712,107、WO 1997/047806、WO 1997/047807、WO 1997/047808及WO 2000/014249中所揭示);产生α-1,6-支化α-1,4-葡聚糖的植物(如WO 2000/73422中所揭示);产生阿塔娜(alternan)的植物(如WO 2000/047727、EP06077301.7、US 5,908,975和EP 0728213中所揭示);
3)产生透明质酸的转基因植物,如(例如)WO 2006/032538、WO 2007/039314、WO2007/039315、WO 2007/039316、JP 2006/304779、及WO 2005/012529中所公开。
本发明还可处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)是具有改变的纤维特性的植物,例如棉花植物。这些植物可通过遗传转化,或通过选择包含赋予该改变的纤维特性的突变的植物来获得,包括:
a)包含改变形式的纤维素合酶基因的植物,例如棉花植物,如WO 1998/000549中所述
b)包含改变形式的rsw2或rsw3同源核酸的植物,例如棉花植物,如WO2004/053219中所述
c)具有增加蔗糖磷酸合酶的表达的植物,例如棉花植物,如WO 2001/017333中所述
d)具有增加蔗糖合酶的表达的植物,例如棉花植物,如WO02/45485中所述
e)其中基于纤维细胞的胞间连丝门控的时间被改变(例如通过下调纤维选择性β1,3-葡聚糖酶)的植物,例如棉花植物,如WO2005/017157中所述
f)具有改变的纤维反应性(例如通过表达包含nodC的N-乙酰基葡糖胺转化酶基因和壳聚糖合成酶(chitinsynthase)基因)的植物,例如棉花植物,如WO2006/136351中所述。
本发明还可处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)是具有改变的油分布(oil profile)性质的植物,例如油菜或相关芸苔属植物。这些植物可通过遗传转化,或通过选择包含赋予该改变的油特性的突变的植物来获得,包括:
a)产生具有高油酸含量的油的植物,例如油菜植物,如例如US 5,969,169、US 5,840,946或US 6,323,392或US 6,063,947中所述。
b)产生具有低亚油酸含量的油的植物,例如油菜植物,如US 6,270828、US 6,169,190或US 5,965,755中所述
c)产生具有低水平饱和脂肪酸的油的植物,例如油菜植物,如例如美国5,434,283或美国专利申请12/668303中所述
还可根据本发明处理的植物或植物品种(由植物生物技术方法获得,例如基因工程)是具有改变的落粒性的植物,例如油菜或相关芸苔属植物。这类植物可通过遗传转化或通过选择含有赋予这种改变的落粒性的突变的植物来获得,并且这类植物包括诸如具有延迟的或降低的落粒性的油籽油菜的植物,如美国专利申请61/135,230、WO2009/068313和WO2010/006732中所述。
本发明还可处理的植物或植物品种(可通过植物生物技术方法,如基因工程获得的)是具有改变的翻译后蛋白质修饰模式的植物,例如烟草植物,例如如WO 2010/121818和WO 2010/145846中所述。
可依据本发明处理的特别有用的转基因植物是含转化事件或转化事件组合的植物,它们是向美国农业部(USDA)动植物卫生检验局(APHIS)提交的要求在美国非管制身份的请求的对象,无论这些请求被准予或仍然处在待审中。在任何时候,该信息很容易从APHIS(美国马里兰州利弗代尔市利弗路4700号(邮编20737)(4700River Road Riverdale,MD 20737,USA))获得,例如在其互联网站上(URL http://www.aphis.usda.gov/brs/not_reg.html)。截止到本申请的提交日,被APHIS审理中或被APHIS准予的要求非管制身份的请求是包括以下信息的请求:
-请求(Petition):请求的识别号。转化事件的技术描述可在各请求文件中找到,而这些请求文件可根据该请求号从APHIS得到,例如从APHIS网站上获得。这些描述通过参考结合于此。
-请求的延长(Extension of Petition):对之前的请求要求延长。
-机构(Institution):提交请求的实体的名称。
-管制项目(Regulated article):涉及的植物物种。
-转基因表型(Transgenic phenotype):通过转化事件赋予植物的特性。
-转化事件或系(Transformation event or line):要求非管制身份的一个或多个事件(有时称为一个或多个系)的名称。
-APHIS文档:与请求相关的APHIS出版的各种文件,它们可以是APHIS要求的。
其它特别有用的含单个转化事件或转化事件组合的植物例如在各个国家或地方性管理机构的数据库中列出(参见,例如http://gmoinfo.jrc.it/gmp_browse.aspx和http://www.agbios.com/dbase.php)。
本发明可处理的特别有用的转基因植物是包含转化事件,或转化事件的组合的植物,其示于例如来自各个国家或地区管理机构的数据库中,包括事件1143-14A(棉花,昆虫控制,未保藏,参见WO 2006/128569);事件1143-51B(棉花,昆虫控制,未保藏,参见WO2006/128570);事件1445(棉花,耐除草剂,未保藏,参见US-A 2002-120964或WO 02/034946);事件17053(水稻,耐除草剂,保藏号为PTA-9843,参见WO 2010/117737);事件17314(水稻,耐除草剂,保藏号为PTA-9844,参见WO 2010/117735);事件281-24-236(棉花,昆虫控制-耐除草剂,保藏号为PTA-6233,参见WO 2005/103266或US-A 2005-216969);事件3006-210-23(棉花,昆虫控制-耐除草剂,保藏号为PTA-6233,参见US-A 2007-143876或WO2005/103266);事件3272(玉米,品质特征,保藏号为PTA-9972,参见WO 2006/098952或US-A2006-230473);事件40416(玉米,昆虫控制-耐除草剂,保藏号为ATCC PTA-11508,参见WO2011/075593);事件43A47(玉米,昆虫控制-耐除草剂,保藏号为ATCC PTA-11509,参见WO2011/075595);事件5307(玉米,昆虫控制,保藏号为ATCC PTA-9561,参见WO 2010/077816);事件ASR-368(常绿草,耐除草剂,保藏号为ATCC PTA-4816,参见US-A 2006-162007或WO 2004/053062);事件B16(玉米,耐除草剂,未保藏,参见US-A 2003-126634);事件BPS-CV127-9(大豆,耐除草剂,保藏号为NCIMB No.41603,参见WO 2010/080829);事件CE43-67B(棉花,昆虫控制,保藏号为DSM ACC2724,参见US-A 2009-217423或WO2006/128573);事件CE44-69D(棉花,昆虫控制,未保藏,参见US-A 2010-0024077);事件CE44-69D(棉花,昆虫控制,未保藏,参见WO 2006/128571);事件CE46-02A(棉花,昆虫控制,未保藏,参见WO 2006/128572);事件COT102(棉花,昆虫控制,未保藏,参见US-A 2006-130175或WO2004/039986);事件COT202(棉花,昆虫控制,未保藏,参见US-A 2007-067868或WO 2005/054479);事件COT203(棉花,昆虫控制,未保藏,参见WO 2005/054480);事件DAS40278(玉米,耐除草剂,保藏号为ATCC PTA-10244,参见WO 2011/022469);事件DAS-59122-7(玉米,昆虫控制-耐除草剂,保藏号为ATCC PTA 11384,参见US-A 2006-070139);事件DAS-59132(玉米,昆虫控制-耐除草剂,未保藏,参见WO 2009/100188);事件DAS68416(大豆,耐除草剂,保藏号为ATCC PTA-10442,参见WO 2011/066384或WO 2011/066360);事件DP-098140-6(玉米,耐除草剂,保藏号为ATCC PTA-8296,参见US-A 2009-137395或WO 2008/112019);事件DP-305423-1(大豆,品质特征,未保藏,参见US-A 2008-312082或WO 2008/054747);事件DP-32138-1(玉米,杂交体系,保藏号为ATCC PTA-9158,参见US-A 2009-0210970或WO2009/103049);事件DP-356043-5(大豆,耐除草剂,保藏号为ATCC PTA-8287,参见US-A2010-0184079或WO 2008/002872);事件EE-1(茄子,昆虫控制,未保藏,参见WO 2007/091277);事件FI117(玉米,耐除草剂,保藏号为ATCC 209031,参见US-A 2006-059581或WO98/044140);事件GA21(玉米,耐除草剂,保藏号为ATCC 209033,参见US-A 2005-086719或WO 98/044140);事件GG25(玉米,耐除草剂,保藏号为ATCC 209032,参见US-A 2005-188434或WO 98/044140);事件GHB119(棉花,昆虫控制-耐除草剂,保藏号为ATCC PTA-8398,参见WO 2008/151780);事件GHB614(棉花,耐除草剂,保藏号为ATCC PTA-6878,参见US-A 2010-050282或WO 2007/017186);事件GJ11(玉米,耐除草剂,保藏号为ATCC 209030,参见US-A2005-188434或WO 98/044140);事件GM RZ13(甜菜,抗病毒性,保藏号为NCIMB-41601,参见WO 2010/076212);事件H7-1(甜菜,耐除草剂,保藏号为NCIMB 41158或NCIMB 41159,参见US-A 2004-172669或WO 2004/074492);事件JOPLIN1(小麦,耐病性,未保藏,参见US-A2008-064032);事件LL27(大豆,耐除草剂,保藏号为NCIMB41658,参见WO 2006/108674或US-A 2008-320616);事件LL55(大豆,耐除草剂,保藏号为NCIMB 41660,参见WO 2006/108675或US-A 2008-196127);事件LL棉花25(棉花,耐除草剂,保藏号为ATCC PTA-3343,参见WO 03/013224或US-A 2003-097687);事件LLRICE06(水稻,耐除草剂,保藏号为ATCC-23352,参见US 6,468,747或WO 00/026345);事件LLRICE601(水稻,耐除草剂,保藏号为ATCC PTA-2600,参见US-A 2008-2289060或WO 00/026356);事件LY038(玉米,品质特征,保藏号为ATCC PTA-5623,参见US-A 2007-028322或WO 2005/061720);事件MIR162(玉米,昆虫控制,保藏号为PTA-8166,参见US-A 2009-300784或WO 2007/142840);事件MIR604(玉米,昆虫控制,未保藏,参见US-A 2008-167456或WO 2005/103301);事件MON15985(棉花,昆虫控制,保藏号为ATCC PTA-2516,参见US-A 2004-250317或WO 02/100163);事件MON810(玉米,昆虫控制,未保藏,参见US-A 2002-102582);事件MON863(玉米,昆虫控制,保藏号为ATCC PTA-2605,参见WO 2004/011601或US-A 2006-095986);事件MON87427(玉米,授粉控制,保藏号为ATCC PTA-7899,参见WO 2011/062904);事件MON87460(玉米,胁迫耐受性,保藏号为ATCC PTA-8910,参见WO 2009/111263或US-A 2011-0138504);事件MON87701(大豆,昆虫控制,保藏号为ATCC PTA-8194,参见US-A 2009-130071或WO 2009/064652);事件MON87705(大豆,品质特征-耐除草剂,保藏号为ATCC PTA-9241,参见US-A 2010-0080887或WO 2010/037016);事件MON87708(大豆,耐除草剂,保藏号为ATCC PTA9670,参见WO 2011/034704);事件MON87754(大豆,品质特征,保藏号为ATCC PTA-9385,参见WO 2010/024976);事件MON87769(大豆,品质特征,保藏号为ATCC PTA-8911,参见US-A 2011-0067141或WO2009/102873);事件MON88017(玉米,昆虫控制-耐除草剂,保藏号为ATCC PTA-5582,参见US-A 2008-028482或WO 2005/059103);事件MON88913(棉花,耐除草剂,保藏号为ATCCPTA-4854,参见WO 2004/072235或US-A 2006-059590);事件MON89034(玉米,昆虫控制,保藏号为ATCC PTA-7455,参见WO 2007/140256或US-A 2008-260932);事件MON89788(大豆,耐除草剂,保藏号为ATCC PTA-6708,参见US-A 2006-282915或WO 2006/130436);事件MS11(油菜,授粉控制-耐除草剂,保藏号为ATCC PTA-850或PTA-2485,参见WO 01/031042);事件MS8(油菜,授粉控制-耐除草剂,保藏号为ATCC PTA-730,参见WO 01/041558或US-A 2003-188347);事件NK603(玉米,耐除草剂,保藏号为ATCC PTA-2478,参见US-A 2007-292854);事件PE-7(水稻,昆虫控制,未保藏,参见WO 2008/114282);事件RF3(油菜,授粉控制-耐除草剂,保藏号为ATCC PTA-730,参见WO 01/041558或US-A 2003-188347);事件RT73(油菜,耐除草剂,未保藏,参见WO 02/036831或US-A 2008-070260);事件T227-1(甜菜,耐除草剂,未保藏,参见WO 02/44407或US-A2009-265817);事件T25(玉米,耐除草剂,未保藏,参见US-A 2001-029014或WO 01/051654);事件T304-40(棉花,昆虫控制-耐除草剂,保藏号为ATCCPTA-8171,参见US-A 2010-077501或WO 2008/122406);事件T342-142(棉花,昆虫控制,未保藏,参见WO 2006/128568);事件TC1507(玉米,昆虫控制-耐除草剂,未保藏,参见US-A2005-039226或WO 2004/099447);事件VIP1034(玉米,昆虫控制-耐除草剂,保藏号为ATCCPTA-3925.,参见WO 03/052073),事件32316(玉米,昆虫控制-耐除草剂,保藏号为PTA-11507,参见WO 2011/084632),事件4114(玉米,昆虫控制-耐除草剂,保藏号为PTA-11506,参见WO 2011/084621)。
本发明的组合物还可用于治疗易于在木材上或木材内部生长的真菌疾病。术语“木材”是指所有类型的木材物种、以及打算用于建筑的这种木材的所有类型的加工产品,例如实木、高密度木材、层压木材和胶合板。本发明处理木材的方法主要在于接触一种或多种本发明化合物或本发明组合物;这包括例如直接施用、喷涂、浸渍、注射或任意其它适合的方法。
在通过本发明方法可控制的植物或作物的疾病中,可提及:
粉状霉菌病,例如:
白粉病(Blumeria diseases),由例如小麦白粉菌(Blumeria graminis)引起;
叉丝单囊壳属病(Podosphaera diseases),由例如白叉丝单囊壳(Podosphaeraleucotricha)引起;
单丝壳属病(Sphaerotheca diseases),由例如苍耳单丝壳(Sphaerothecafuliginea)引起;
钩丝壳属病(Uncinula diseases),例如由葡萄钓丝壳(Uncinula necator)引起;
锈病,例如:
胶锈菌属病(Gymnosporangium diseases),由例如赛宾锈菌(Gymnosporangiumsabinae)引起;
驼孢锈病(Hemileia diseases),由例如咖啡驼孢锈菌(Hemileia vastatrix)引起;
层锈菌属病(Phakopsora diseases),由例如豆薯层锈菌(Phakopsorapachyrhizi)或山马蝗层锈菌(Phakopsora meibomiae)引起;
柄锈菌属病(Puccinia diseases),例如由隐匿柄锈菌(Puccinia recondite)引起;
单胞锈菌属病(Uromyces diseases),由例如疣顶单胞锈菌(Uromycesappendiculatus)引起;
卵菌病(Oomycete diseases),例如:
盘梗霉属病(Bremia diseases),由例如苣盘梗霉(Bremia lactucae)引起;
霜霉属病(Peronospora diseases),由例如豌豆霜霉(Peronospora pisi)或芸苔霜霉(P.brassicae)引起;
疫霉属病(Phytophthora diseases),由例如致病疫霉(Phytophthorainfestans)引起;
单轴霉属病(Plasmopara diseases),由例如葡萄生单轴霉(Plasmoparaviticola)引起;
假霜霉属病(Pseudoperonospora diseases),由例如葎草霜霉(Pseudoperonospora humuli)或黄瓜霜霉(Pseudoperonospora cubensis)引起的;
腐霉属病(Pythium diseases),由例如终极腐霉(Pythium ultimum)引起;
叶斑病、叶疱和叶枯病,例如:
支链孢属病(Alternaria diseases),例如由茄链格孢(Alternaria solani)引起;
尾孢霉属病(Cercospora diseases),由例如甜菜生尾孢(Cercospora beticola)引起;
金孢子菌属病(Cladiosporum diseases),例如由瓜枝孢(Cladiosporiumcucumerinum)引起;
旋孢腔菌病(Cochliobolus diseases),例如由禾旋孢腔菌(Cochliobolussativus)引起;
刺盘孢属病(Colletotrichum diseases),由例如豆刺盘孢(Colletotrichumlindemuthianum)引起;
油橄榄孔雀斑病(Cycloconium diseases),由例如油橄榄孔雀斑菌(Cycloconiumoleaginum)引起;
腐皮壳菌层病(Diaporthe diseases),由例如柑桔间座壳(Diaporthe citri)引起;
痂囊腔菌属病(Elsinoe diseases),由例如柑桔痂囊腔菌(Elsinoe fawcettii)引起;
长孢属病(Gloeosporium diseases),由例如悦色盘长孢(Gloeosporiumlaeticolor)引起;
小丛壳属病(Glomerella diseases),由例如围小丛壳(Glomerella cingulata)引起;
球座菌属病(Guignardia diseases),由例如葡萄球座菌(Guignardiabidwellii)引起;
小球腔菌属病(Leptosphaeria diseases),由例如十字花科小球腔菌(Leptosphaeria maculans)、颖枯小球腔菌(Leptosphaeria nodorum)引起;
稻瘟病(Magnaporthe diseases),由例如稻瘟菌(Magnaporthe grisea)引起;
球腔菌属病(Mycosphaerella diseases),由例如禾生球腔菌(Mycosphaerellagraminicola)、落花生球腔菌(Mycosphaerella arachidicola)、香蕉黑条叶斑菌(Mycosphaerella fijiensis)引起;
壳针孢属病(Phaeosphaeria diseases),由例如颖枯壳针孢(Phaeosphaerianodorum)引起;
核腔菌属病(Pyrenophora diseases),例如由圆核腔菌(Pyrenophora teres)引起;
柱隔孢属病(Ramularia diseases),由例如辛加柱隔孢(Ramularia collo-cygni)引起;
喙孢属病(Rhynchosporium diseases),由例如黑麦喙孢(Rhynchosporiumsecalis)引起;
壳针孢属病(Septoria diseases),由例如芹菜小壳针孢(Septoria apii)或番茄壳针孢(Septoria lycopersici)引起;
核瑚菌病(Typhula diseases),由例如肉色核瑚菌(Typhula incarnata)引起;
黑星菌属病(Venturia diseases),例如由苹果黑星菌(Venturia inaequalis)引起;
根病和茎病,例如:
伏革菌病(Corticium diseases),由例如禾伏革菌(Corticium graminearum)引起;
镰孢菌(霉)属病(Fusarium diseases),由例如尖镰孢(Fusarium oxysporum)引起;
鲟形属病(Gaeumannomyces diseases),由例如禾顶囊壳(Gaeumannomycesgraminis)引起;
丝核菌属病(Rhizoctonia diseases),由例如立枯丝核菌(Rhizoctonia solani)引起;
塔普斯病(Tapesia diseases),由例如塔普斯梭状芽胞杆菌(Tapesiaacuformis)引起;
根串珠霉属病(Thielaviopsis diseases),由例如根串珠霉(Thielaviopsisbasicola)引起;
耳穗和圆锥花序病,例如:
链格孢属病(Alternaria diseases),由例如链格孢(Alternaria spp.)引起;;
曲霉病(Aspergillus diseases),由例如黄曲霉(Aspergillus flavus)引起;
枝孢病(Cladosporium diseases),由例如枝孢(Cladosporium spp.)引起;;
麦角菌属病(Claviceps diseases),由例如麦角菌(Claviceps purpurea)引起;
镰孢菌(霉)属病(Fusarium diseases),由例如大刀镰孢(Fusarium culmorum)引起;
赤霉病(Gibberella diseases),由例如玉蜀黍赤霉(Gibberella zeae)引起;
水稻云形病(Monographella diseases),由例如水稻云形菌(Monographellanivalis)引起;
黑穗病和腥黑穗病,例如:
轴黑粉菌属病(Sphacelotheca diseases),由例如丝轴黑粉菌(Sphacelothecareilinana)引起;
腥黑粉菌属病(Tilletia diseases),由例如小麦网腥黑粉菌(Tilletia caries)引起;
条黑粉菌属病(Urocystis diseases),由例如隐条黑粉菌(Urocystis occulta)引起;
黑粉菌属病(Ustilago diseases),由例如裸黑粉菌(Ustilago nuda)引起;
果实腐烂和霉菌病,例如:
曲霉病(Aspergillus diseases),由例如黄曲霉(Aspergillus flavus)引起;
葡萄孢菌属病(Botrytis diseases),由例如葡萄孢菌(Botrytis cinerea)引起的;
青霉病(Penicillium diseases),由例如甘薯青霉(Penicillium expansum)引起;
核盘菌属病(Sclerotinia diseases),由例如核盘菌(Sclerotiniasclerotiorum)引起;
轮枝孢属病(Verticilium diseases),由例如黑白轮枝孢(Verticilliumalboatrum)引起;
种子和土壤中的腐烂、发霉、枯萎、腐败以及猝倒病:
链格孢病(Alternaria diseases),由例如芥链格孢(Alternaria brassicicola)引起;
丝囊霉属病(Aphanomyces diseases),由例如豌豆丝囊霉(Aphanomyceseuteiches)引起;
壳二孢属病(Ascochyta diseases),由例如晶状体二胞菌(Ascochyta lentis)引起;
曲霉病(Aspergillus diseases),由例如黄曲霉(Aspergillus flavus)引起;
枝孢病(Cladosporium diseases),由例如多主枝孢(Cladosporium herbarum)引起;
旋孢腔菌病(Cochliobolus diseases),由例如禾旋孢腔菌(Cochliobolussativus)引起;
(分生孢子形式(Conidiaform):内脐蠕孢属(Drechslera)、平脐蠕孢属(Bipolaris)(同义名):长蠕孢属(Helminthosporium));
刺盘孢病(Colletotrichum diseases),由例如粒状体刺盘孢(Colletotrichumcoccodes)引起;
镰孢菌(霉)属病(Fusarium diseases),由例如大刀镰孢(Fusarium culmorum)引起;
赤霉病(Gibberella diseases),由例如玉蜀黍赤霉(Gibberella zeae)引起;
壳球孢病(Macrophomina diseases),由例如豆类壳球孢(Macrophominaphaseolina)引起;
水稻云形病(Monographella diseases),由例如水稻云形菌(Monographellanivalis)引起;
青霉病(Penicillium diseases),由例如甘薯青霉(Penicillium expansum)引起;
茎点霉病(Phoma diseases),由例如黑胫茎点霉(Phoma lingam)引起;
拟茎点霉病(Phomopsis diseases),由例如大豆茎点霉(Phomopsis sojae)引起;
疫霉属病(Phytophthora diseases),由例如恶疫霉(Phytophthora cactorum)引起;
核腔菌病(Pyrenophora diseases),由例如麦类核腔菌(Pyrenophora graminea)引起;
梨孢属病(Pyricularia diseases),由例如稻梨孢(Pyricularia oryzae)引起的;
腐霉属病(Pythium diseases),由例如终极腐霉(Pythium ultimum)引起;
丝核菌属病(Rhizoctonia diseases),由例如立枯丝核菌(Rhizoctonia solani)引起;
根霉病(Rhizopus diseases),由例如米根霉(Rhizopus oryzae)引起;
小核菌病(Sclerotium diseases),由例如齐整小核菌(Sclerotium rolfsii)引起的;
壳针孢病(Septoria diseases),例如由颖枯壳针孢(Septoria nodorum)引起;
核瑚菌病(Typhula diseases),由例如肉色核瑚菌(Typhula incarnata)引起;
轮枝孢病(Verticillium diseases),由例如大丽花轮枝孢(Verticilliumdahliae)引起;
溃疡、开裂及梢枯病,例如:
丛赤壳属病(Nectria diseases),由例如干癌丛赤壳菌(Nectria galligena)引起;
枯萎病,例如:
链核盘菌属病(Monilinia diseases),由例如核果链核盘菌(Monilinia laxa)引起;
叶泡或卷叶病,例如:
外囊菌属病(Taphrina diseases),由例如畸形外囊菌(Taphrina deformans)引起;
木质植物衰退病,例如:
依科病(Esca diseases),由例如根霉格孢菌(Phaeomoniella clamydospora)引起;
葡萄顶枯病(Eutypa dyeback),由例如葡萄藤猝倒病菌(Eutypa lata)引起;
荷兰榆树病(Dutch elm disease),由例如角果属螨(Ceratocystsc ulmi)引起;
花和种子的疾病,例如:
葡萄孢菌属病(Botrytis diseases),由例如葡萄孢菌(Botrytis cinerea)引起的;
根茎类疾病,例如:
丝核菌属病(Rhizoctonia diseases),由例如立枯丝核菌(Rhizoctonia solani)引起;
长蠕孢菌属病(Helminthosporium diseases),由例如立枯长蠕孢(Helminthosporium solani)引起。
本发明的化合物还可用于制备用于治疗性或预防性地处理人或动物真菌疾病的组合物,所述人或动物真菌疾病是例如霉菌病(mycose)、皮肤病、癣菌病及念珠菌病、或由曲霉属(Aspergillus spp.)(例如烟曲霉(Aspergillus fumigatus))引起的疾病。
现将参照下列化合物实施例的表1以及下列制备或功效实施例对本发明的各个方面予以说明。
下表1以非限制性的方式对本发明化合物的实例予以说明。
在表1中,下列缩写用于本发明一般结构(I)的特定要求的要素“A1”和“A2”:
表1
如下所示,我们描述了表1的实施例的双键几何结构:
logP值是依据EEC指令79/831附录V.A8(EEC Directive 79/831 Annex V.A8)由HPLC(高效液相色谱)在反相柱上用下列方法测定的:
[a]LC-MS的测定是在以下条件下完成的:在pH=2.7的条件下用0.1%甲酸的水溶液并使用乙腈(包含0.1%甲酸)作为洗脱剂,线性梯度为10%乙腈至95%乙腈。
使用logP值已知的非支链烷2-酮(包含3~16个碳原子)进行校准(logP值是采用两个相邻烷酮之间的线性内插法由保留时间确定的)。使用200纳米至400纳米的紫外光谱,在色谱信号最大值处确定λmax值。
NMR峰列表
所选实施例的1H-NMR数据以1H-NMR-峰列表的形式列出。对于各信号峰列出的δ值,单位是ppm,信号强度在圆括号内。δ值(信号强度)对之间以分号隔开。
因此,实例峰列表具有如下的形式:
δ1(强度1);δ2(强度2);........;δi(强度i);......;δn(强度n)
NMR峰列表1
尖锐信号的强度与NMR光谱的图像实例中的信号高度(以厘米计)相关,并显示了信号强度的真实关系。在宽信号中,可以显示几个峰或信号的中间部分以及它们相对于光谱中最强信号的相对强度。
为了校准1H光谱的化学位移,特别是在DMSO中测得光谱时,我们使用四甲基硅烷和/或所用溶剂的化学位移。因此,在NMR峰列表中,可存在四甲基硅烷峰,但不是一定存在。
1H-NMR峰列表与典型的1H-NMR图像类似,因此其通常包含在典型NMR-解读中所列出的所有峰。
另外,它们还可显示如溶剂、目标化合物的立体异构体(也是本发明的目的)和/或杂质峰的典型1H-NMR图像信号。
为了显示溶剂和/或水的δ范围内的化合物信号,我们的1H-NMR峰列表中显示了常见溶剂峰(例如DMSO在DMSO-D6中的峰和水的峰),并且平均来看通常具有高强度。
平均来看,目标化合物的立体异构体的峰和/或杂质的峰与目标化合物(例如纯度>90%)的峰相比通常具有较低的强度。
此类立体异构体和/或杂质对于特定制备过程来说可能是典型的。因此,它们的峰可以通过“副产物指纹(side-products-fingerprints)”帮助识别我们的制备过程的重现性。
专业人员通过使用已知的方法(MestreC,ACD-模拟,还可使用经验评估预期值)计算目标化合物的峰,并且根据需要任选地使用其它强度过滤器,从而可以分离目标化合物的峰。该分离与在典型1H-NMR解读中挑选相关峰类似。
可在研究公开数据库第564025号(Research Disclosure Database Number564025)的公开发表物“专利申请中的NMR峰列表数据的引用(Citation of NMR PeaklistData within Patent Applications)”中找到含峰列表的NMR数据描述的其它细节。
下表2以非限制性的方式对本发明式(V)化合物的实例予以说明。
在表2中,下列缩写用于本发明一般结构(I)的特定要求的要素“A1”和“A2”:
表2
如下所示,我们描述了表2的实施例的双键几何结构:
logP值是依据EEC指令79/831附录V.A8(EEC Directive 79/831 Annex V.A8)由HPLC(高效液相色谱)在反相柱上用下列方法测定的:
[a]LC-MS的测定是在以下条件下完成的:在pH=2.7的条件下用0.1%甲酸的水溶液并使用乙腈(包含0.1%甲酸)作为洗脱剂,线性梯度为10%乙腈至95%乙腈。
使用logP值已知的非支链烷2-酮(包含3-16个碳原子)进行校准(logP值是采用两个相邻烷酮之间的线性内插法由保留时间确定的)。使用200纳米至400纳米的紫外光谱,在色谱信号最大值处确定λmax值。
NMR峰列表
所选实施例的1H-NMR数据以1H-NMR-峰列表的形式列出。对于各信号峰列出的δ值,单位是ppm,信号强度在圆括号内。δ值(信号强度)对之间以分号隔开。
因此,实例峰列表具有如下的形式:
δ1(强度1);δ2(强度2);........;δi(强度i);......;δn(强度n)
NMR峰列表2
尖锐信号的强度与NMR光谱的图像实例中的信号高度(以厘米计)相关,并显示了信号强度的真实关系。在宽信号中,可以显示几个峰或信号的中间部分以及它们相对于光谱中最强信号的相对强度。
为了校准1H光谱的化学位移,特别是在DMSO中测得光谱时,我们使用四甲基硅烷和/或所用溶剂的化学位移。因此,在NMR峰列表中,可存在四甲基硅烷峰,但不是必须的一定存在。
1H-NMR峰列表与典型的1H-NMR图像类似,因此其通常包含在典型NMR-解读中所列出的所有峰。
另外,它们还可显示如溶剂、目标化合物的立体异构体(也是本发明的目的)和/或杂质峰的典型1H-NMR图像信号。
为了显示溶剂和/或水的δ范围内的化合物信号,我们的1H-NMR峰列表中显示了常见溶剂峰(例如DMSO在DMSO-D6中的峰和水的峰),并且平均来看通常具有高强度。
平均来看,目标化合物的立体异构体的峰和/或杂质的峰与目标化合物(例如纯度>90%)的峰相比通常具有较低的强度。
此类立体异构体和/或杂质对于特定制备过程来说可能是典型的。因此,它们的峰可以通过“副产物指纹(side-products-fingerprints)”帮助识别我们的制备过程的重现性。
专业人员通过使用已知的方法(MestreC,ACD-模拟,还可使用经验评估预期值)计算目标化合物的峰,并且根据需要任选地使用其它强度过滤器,从而可以分离目标化合物的峰。该分离与在典型1H-NMR解读中挑选相关峰类似。
可在研究公开数据库第564025号的公开发表物“专利申请中的NMR峰列表数据的引用(Citation of NMR Peaklist Data within Patent Applications)”中找到含峰列表的NMR数据描述的其它细节。
下表3以非限制性的方式对本发明式(VII)化合物的实例予以说明。
表3
logP值是依据EEC指令79/831附录V.A8(EEC Directive 79/831 Annex V.A8)由HPLC(高效液相色谱)在反相柱上用下列方法测定的:
[a]LC-MS的测定是在以下条件下完成的:在pH=2.7的条件下用0.1%甲酸的水溶液并使用乙腈(包含0.1%甲酸)作为洗脱剂,线性梯度为10%乙腈至95%乙腈。
使用logP值已知的非支链烷2-酮(包含3-16个碳原子)进行校准(logP值是采用两个相邻烷酮之间的线性内插法由保留时间确定的)。使用200纳米至400纳米的紫外光谱,在色谱信号最大值处确定λmax值。
NMR峰列表
所选实施例的1H-NMR数据以1H-NMR-峰列表的形式列出。对于各信号峰列出的□值,单位是ppm,信号强度在圆括号内。□值(信号强度)对之间以分号隔开。
因此,实例峰列表具有如下的形式:
δ1(强度1);δ2(强度2);........;δi(强度i);......;δn(强度n)
NMR峰列表3
实施例VII-1,溶剂:DMSO,光谱仪:499.93MHz
8.1468(2.84);8.1323(3.08);8.1301(2.62);7.8209(0.72);7.8061(1.66);7.7912(1.01);7.6541(2.15);7.6385(3.33);7.6228(1.70);3.3813(16.00);3.3525(3.79);2.5148(0.84);2.5115(1.10);2.5082(0.84))
尖锐信号的强度与NMR光谱的图像实例中的信号高度(以厘米计)相关,并显示了信号强度的真实关系。在宽信号中,可以显示几个峰或信号的中间部分以及它们相对于光谱中最强信号的相对强度。
为了校准1H光谱的化学位移,特别是在DMSO中测得光谱时,我们使用四甲基硅烷和/或所用溶剂的化学位移。因此,在NMR峰列表中,可存在四甲基硅烷峰,但不是一定存在。
1H-NMR峰列表与典型的1H-NMR图像类似,因此其通常包含在典型NMR-解读中所列出的所有峰。
另外,它们还可显示如溶剂、目标化合物的立体异构体(也是本发明的目的)和/或杂质峰的典型1H-NMR图像信号。
为了显示溶剂和/或水的□范围内的化合物信号,我们的1H-NMR峰列表中显示了常见溶剂峰(例如DMSO在DMSO-D6中的峰和水的峰),并且平均来看通常具有高强度。
平均来看,目标化合物的立体异构体的峰和/或杂质的峰与目标化合物(例如纯度>90%)的峰相比通常具有较低的强度。
此类立体异构体和/或杂质对于特定制备过程来说可能是典型的。因此,它们的峰可以通过“副产物指纹(side-products-fingerprints)”帮助识别我们的制备过程的重现性。
专业人员通过使用已知的方法(MestreC,ACD-模拟,还可使用经验评估预期值)计算目标化合物的峰,并且根据需要任选地使用其它强度过滤器,从而可以分离目标化合物的峰。该分离与在典型1H-NMR解读中挑选相关峰类似。
可在研究公开数据库第564025号的公开发表物“专利申请中的NMR峰列表数据的引用(Citation of NMR Peaklist Data within Patent Applications)”中找到含峰列表的NMR数据描述的其它细节。
实施例A
疫霉测试(番茄)/预防性的
溶剂:49重量份的N,N-二甲基甲酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了获得活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂进行混合,并用水将浓缩物稀释至所需的浓度。
为了测试预防活性,使用活性化合物的制剂在所述施用比率下对幼龄植物进行喷涂。在该处理1天后,用致病疫霉(Phytophthora infestans)的水性孢子悬浮液对上述植物进行接种。将所述植物在约22℃、相对大气湿度为100%的温育箱中保持1天。然后将所述植物放置在约20℃、相对大气湿度为96%的温育箱中。
在接种7天后对测试进行评估。0%表示相当于未处理的对照样的功效,100%功效表示没有观察到疾病。
在该测试中,本发明下列化合物显示出在100ppm的活性成分的浓度条件下功效为70%甚至更高。
实施例B
单轴霉测试(葡萄树)/预防性的
溶剂:24.5重量份的丙酮
24.5重量份的二甲基乙酰胺
乳化剂:1重量份的烷基芳基聚乙二醇醚
为了获得活性化合物的合适制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂进行混合,并用水将浓缩物稀释至所需的浓度。
为了测试预防活性,使用活性化合物的制剂在所述施用比率下对幼龄植物进行喷涂。待所述喷涂涂料已干燥后,用葡萄生单轴霉(Plasmopara viticola)的水性孢子悬浮液对上述植物进行接种,然后将该植物在大约20℃,100%的相对大气湿度的条件下,在温育箱中保持1天。随后将该植物放置于大约21℃,大约90%的相对大气湿度的条件下的温室中4天。然后对该植物喷薄雾,并放置于温育箱中1天。
在接种6天后对测试进行评估。0%表示相当于未处理的对照样的功效,100%功效表示没有观察到疾病。
在该测试中,本发明下列化合物显示出在10ppm的活性成分的浓度条件下功效为70%甚至更高。
表
单轴霉测试(葡萄树)/预防性的
实施例C
腐霉测试(黄瓜)/种子处理
该测试在温室条件下进行。
将用溶解在N-甲基-2-吡咯烷酮并用水稀释成所需剂量的活性化合物或化合物组合处理过的黄瓜种子播种在6*6厘米的盆中,该盆含有4厘米的蒸过的田间土与砂子的1:1混合物。
用瓜果腐霉(Pythium aphanidermatum)的菌丝体片段温育珍珠岩。在经处理的棉花种子之间撒播5mL经感染的珍珠岩。然后,种子用蒸过的田间土和砂子的1:1混合物覆盖。在24℃和80%相对湿度条件下在温室中使盆温育7天。
通过新生幼苗的计数来评估。0%表示相当于对照样的功效,100%功效表示所有幼苗都已形成。
在该测试中,本发明下列化合物显示出在活性成分剂量为10g/dt(g/分吨)种子的条件下功效为70%甚至更高。
实例编号 | 功效% |
2 | 98 |
3 | 95 |
15 | 98 |
168 | 92 |
199 | 99 |
226 | 99 |
282 | 100 |
342 | 100 |
实施例D
腐霉测试(棉花)/种子处理
该测试在温室条件下进行。
将用溶解在N-甲基-2-吡咯烷酮并用水稀释成所需剂量的活性化合物或化合物组合处理过的棉花种子播种在6*6厘米的盆中,该盆含有4厘米的蒸过的田间土壤与砂子的1:1混合物。
用终极腐霉(Pythium ultimum)的菌丝体片段温育珍珠岩。在经处理的棉花种子之间撒播1mL经感染的珍珠岩。再用轻质膨胀粘土骨料覆盖种子。在20℃和80%相对湿度条件下在温室中使盆温育7天。
通过新生幼苗的计数来评估。0%表示相当于对照样的功效,100%功效表示所有幼苗都已形成。
在该测试中,本发明下列化合物显示出在活性成分剂量为10g/dt(g/分吨)种子的条件下功效为70%甚至更高。
实施例E
腐霉测试(谷类)/种子处理
该测试在温室条件下进行。
将用溶解在N-甲基-2-吡咯烷酮并用水稀释成所需剂量的活性化合物或化合物组合处理过的谷物种子播种在6*6厘米的盆中,该盆含有4厘米的蒸过的田间土壤与砂子的1:1混合物。
用畸雌腐霉(Pythium irregulare)的菌丝体片段温育珍珠岩。在经处理的棉花种子之间撒播5mL经感染的珍珠岩。然后,种子用蒸过的田间土和砂子的1:1混合物覆盖。使盆在温室中于10℃和80%相对湿度温育7天,然后在20℃和80%相对湿度温育14天。
通过新生幼苗的计数来评估。0%表示相当于对照样的功效,100%功效表示所有幼苗都已形成。
在该测试中,本发明下列化合物显示出在活性成分剂量为10g/dt(g/分吨)种子的条件下功效为70%甚至更高。
实例编号 | 功效% |
2 | 100 |
3 | 100 |
15 | 100 |
168 | 100 |
199 | 100 |
226 | 90 |
282 | 90 |
342 | 100 |
实施例F:对致病疫霉(Phytophthora infestans)(番茄晚疫病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料浓度。
将番茄植株(Rentita品种)种植在起始杯中的50/50泥炭土-火山灰基质上,并在20~25℃生长,在Z12阶段时通过喷洒上述水性悬浮液处理该植物。
用不含活性材料的水溶液处理植物,作为对照。在24小时之后,通过向植物喷洒致病疫霉(Phytophthora infestans)孢子水性悬浮液(20,000个孢子/毫升)来污染所述植物。这些孢子收集自受感染的植物。使受污染的番茄植物在约5~20℃和潮湿氛围下培养5天。在污染后5天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)保护:
实施例G:对灰葡萄孢子(Botrytis cinerea)(灰霉)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料。
将小黄瓜植物(Vert petit de Paris品种)放置在起始杯中,种植到50/50泥炭土-火山灰培养基中,并在18~20℃生长,在子叶Z11阶段,通过向植物喷洒上述方法制备的活性组分来处理该植物。
用不含活性材料的水溶液处理植物,作为对照。
24小时之后,通过在植物叶子的上表面喷洒低温保存的灰葡萄孢子的水性悬浮液(50,000个孢子/mL)来污染植物。这些孢子被悬浮在由以下物质组成的营养溶液中:
-10g/L的PDB;
-50g/L的D-果糖;
-2g/L的NH4NO3;
-1g/L的KH2PO4。
所述受污染的黄瓜植物在气候室中于17℃(昼/夜)和80%相对湿度条件下放置4/5天。
在污染后4/5天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实施例H:对黄瓜白粉病(Sphaerotheca fuliginea)(葫芦霉粉病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料。
将黄瓜植物(Vert petit de Paris种)放置在起始杯中,种植到50/50泥炭土-火山灰培养基中,并在20℃/23℃生长,在子叶Z10阶段时通过喷洒上述水性悬浮液处理该植物。用不含活性材料的水溶液处理植物,作为对照。
在24小时之后,通过向植物喷洒黄瓜白粉病(Sphaerotheca fuliginea)孢子水性悬浮液(100,000个孢子/毫升)将植物污染。这些孢子收集自受污染的植物。受污染的小黄瓜植物在20℃/25℃和60/70%相对湿度的条件下培养。
在污染后12天,与对照植物相比较进行分级(功效百分数)。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实例编号 | 功效% |
83 | 85 |
124 | 80 |
190 | 98 |
197 | 80 |
209 | 75 |
211 | 72 |
212 | 100 |
实施例I:对菜豆锈病菌(Uromyces appendiculatus)(豆褐锈病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料。
将小麦植物(Saxa品种)在起始杯中播种到50/50泥炭土-火山灰培养基上,并在24℃生长,在2-叶阶段(9厘米高),通过喷洒按照上述制备的活性组分水悬浮液来处理。
用不含活性材料的水溶液处理植物,作为对照。
在24小时之后,通过向植物叶子喷洒菜豆锈病菌(Uromyces appendiculatus)孢子水性悬浮液(150,000个孢子/毫升)将植物污染。这些孢子收集自10天龄的受污染小麦,并悬浮在含2.5毫升/升的10%的吐温80的水中。污染后的小麦植物在约20℃和100%相对湿度的条件下温育24小时,然后在20℃和70%的相对湿度温育10天。在污染后10天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实例编号 | 功效% |
39 | 81 |
43 | 75 |
62 | 71 |
83 | 75 |
99 | 71 |
111 | 72 |
113 | 79 |
140 | 73 |
171 | 82 |
185 | 75 |
190 | 83 |
197 | 89 |
206 | 91 |
212 | 100 |
216 | 71 |
228 | 70 |
258 | 93 |
276 | 89 |
280 | 83 |
295 | 70 |
400 | 94 |
406 | 79 |
实施例K:圆核腔菌(Pyrenophora teres)(大麦网斑病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料浓度。
将大麦植物(Plaisant品种)在起始杯中播种到50/50泥炭土-火山灰培养基中,并在22℃(12小时)/20℃(12小时)生长,在1-叶阶段(10厘米高),通过喷洒上述方法制备的活性组分来处理该植物。
用不含活性材料的水溶液处理植物,作为对照。
在24小时之后,通过对植物喷洒圆核腔菌(Pyrenophora teres)孢子的水性悬浮液(12,000个孢子/毫升)而使它们受到污染。这些孢子收集自12天龄的培养物。污染的大麦植物在约20℃和100%相对湿度的条件下温育24小时,然后在80%的相对湿度下温育12天。
在污染后12天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好(至少70%)的功效:
实例编号 | 功效% |
35 | 100 |
36 | 71 |
53 | 70 |
71 | 70 |
84 | 70 |
117 | 79 |
212 | 97 |
250 | 79 |
255 | 70 |
256 | 90 |
268 | 96 |
379 | 100 |
实施例l:对禾生球腔菌(Mycosphaerella graminicola)(小麦叶斑枯病)的体内
测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料浓度。
将小麦植物(Scipion品种)在起始杯中播种在50/50泥炭土-火山灰培养基上并在22℃(12小时)/20℃(12小时)生长,在1-叶阶段(10厘米高),通过喷洒按照上述制备的水悬浮液来处理。用不含活性材料的水溶液处理植物,作为对照。
在24小时之后,通过向植物喷洒低温保存的禾生球腔菌(Mycosphaerellagraminicola)孢子的水性悬浮液(500,000个孢子/毫升)将植物污染。污染后的小麦植物在18℃和100%相对湿度的条件下培养72小时,然后在90%的相对湿度培养21~28天。
在污染后21~28天,与对照植物相比较进行分级(%功效)。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实例编号 | 功效% | 实例编号 | 功效% | |
30 | 86 | 190 | 100 | |
43 | 91 | 197 | 96 | |
57 | 79 | 207 | 79 | |
67 | 90 | 212 | 100 | |
71 | 88 | 223 | 80 | |
77 | 71 | 248 | 86 | |
83 | 93 | 250 | 96 | |
108 | 71 | 255 | 88 | |
111 | 100 | 270 | 86 | |
117 | 90 | 308 | 100 | |
130 | 86 | 330 | 83 | |
151 | 92 | 341 | 70 | |
158 | 80 | 384 | 70 | |
172 | 86 | 406 | 79 | |
173 | 73 |
实施例M:对隐匿柄锈菌(Puccinia recondita)(褐锈病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料。
将小麦植物(Scipion品种)在起始杯中播种在50/50泥炭土-火山灰培养基上并在22℃(12小时)/20℃(12小时)生长,在1-叶阶段(10厘米高),通过喷洒按照上述制备的水悬浮液来处理。
用不含活性材料的水溶液处理植物,作为对照。
在24小时之后,通过向植物叶子喷洒隐匿柄锈菌孢子水性悬浮液(100,000个孢子/毫升)将植物污染。这些孢子收集自10天龄的受污染小麦,并悬浮在含2.5毫升/升的10%的吐温80的水中。污染后的小麦植物在20℃和100%相对湿度的条件下培养24小时,然后在20℃和70%的相对湿度培养10天。在污染后10天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实例编号 | 功效% | 实例编号 | 功效% | |
36 | 75 | 209 | 88 | |
39 | 98 | 211 | 71 | |
43 | 94 | 212 | 89 | |
63 | 75 | 215 | 81 | |
67 | 98 | 228 | 81 | |
73 | 81 | 233 | 98 | |
83 | 89 | 258 | 81 | |
88 | 78 | 280 | 98 | |
120 | 98 | 292 | 75 | |
131 | 81 | 308 | 94 | |
140 | 86 | 317 | 81 | |
172 | 89 | 324 | 75 | |
173 | 89 | 325 | 75 | |
185 | 78 | 351 | 75 | |
190 | 94 | 384 | 79 | |
191 | 89 | 395 | 72 | |
197 | 94 | 406 | 81 |
实施例N:对芸苔链格孢(Alternaria brassicae)(十字花科植物叶枯病)的体内
测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料。
将小红萝卜植物(Pernot品种)在起始杯中播种到50/50泥炭土-火山灰培养基中,并在18~20℃生长,在子叶阶段,通过喷洒上述方法制备的活性组分来处理该植物。
用不含活性材料的丙酮/吐温/水混合物处理植物,作为对照。
在24小时之后,通过向植物喷洒芸苔链格孢子水性悬浮液(40,000个孢子/厘米3)将植物污染。这些孢子收集自12~13天龄的培养物。
受污染的小红萝卜植物在约18℃和潮湿氛围下培养6~7天。
在污染后6~7天,与对照植物相比较进行分级。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)保护:
实例编号 | 功效% |
34 | 100 |
39 | 83 |
111 | 70 |
209 | 70 |
212 | 70 |
262 | 83 |
308 | 90 |
364 | 92 |
实施例O:对稻瘟菌(Pyricularia grisea)(稻瘟病)的体内测试
测试用的活性组分通过以下步骤制备:在丙酮/吐温/DMSO混合物中均化,然后用水稀释,获得所需的活性材料浓度。
将稻植物(Koshihikari品种)在起始杯中播种到50/50泥炭土-火山灰培养基中,并在25℃生长,在2-叶阶段(10厘米高),通过喷洒上述方法制备的活性成分来处理该植物。用不含有活性材料的丙酮/吐温/DMSO/水混合物处理植物作为对照。
在24小时之后,通过向植物喷洒稻瘟菌(Pyricularia grisea)孢子水性悬浮液(40,000个孢子/毫升)来污染所述植物。这些孢子收集自17天龄的培养物,并悬浮于包含2.5g/l明胶的水中。使受污染的稻植物在25℃和80%相对湿度的条件下培养6天。
在污染后6天,与对照植物相比较进行分级(功效百分数)。
在这些条件下,使用500ppm剂量的以下化合物观察到良好的(至少70%)或完全的保护:
实例编号 | 功效% |
42 | 71 |
95 | 70 |
109 | 70 |
167 | 96 |
171 | 80 |
227 | 96 |
265 | 70 |
306 | 90 |
化学
以下实施例以非限制性的方式对依据本发明的通式(I)化合物的制备和药效予以说明。
制备实施例1:根据方法P1的3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物1)
步骤1:
向内含(2Z)-(羟基亚氨基)(苯基)乙腈(2.5g,17.10mmol,1当量)的100ml乙腈和10ml DMF溶液添加叔丁基[6-(氯甲基)吡啶-2-基]氨基甲酸酯(4.15g,17.10mmol,1当量),然后添加碘化钾(283mg,1.71mmol,0.1当量)和碳酸铯(8.36g,25.65mmol,1.5当量)。使该反应在室温搅拌过夜。然后,蒸发溶剂并使剩余物溶解于EtOAc(100ml)。有机层用H2O洗涤并用MgSO4干燥,然后浓缩。获得白色固态的叔丁基{6-[({[(Z)-氰基(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯(5.39g,产率80%,仅1种肟异构体)。
步骤2:
向内含叔丁基{6-[({[(Z)-氰基(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯(5.4g,15.32mmol,1当量)的DCM(200ml)溶液添加TFA(17.47g,153mmol,10当量)。然后使该溶液回流12小时。所述反应通过添加水性饱和NaHCO3淬灭,并用EtOAc(3x 50ml)萃取。合并有机物,用MgSO4干燥并浓缩以获得(2Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)乙腈(3.86g,产率89%)。
步骤3:根据方法P1制备(Z)-2-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(化合物V-3)
向内含(2Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)乙腈(4g,15.85mmol,1当量)的iPrOH/H2O(10/1,110ml)悬液添加盐酸羟胺(3.30g,47.56mmol,3当量)和碳酸钾(6.57g,47.56mmol,3当量)。使该反应升温至80℃6小时,然后蒸发溶剂至3/4。剩余物用EtOAc(3x 50ml)萃取,并用水性饱和NaCl洗涤。合并有机物,用MgSO4干燥,并浓缩以获得白色固态的(Z)-2-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(5g,产率99%)。
步骤4:根据方法P1制备3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(化合物23)
向内含(1Z,2Z)-2-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(3g,10.51mmol,1当量)的DMF(50ml)溶液添加CDI(1.70g,10.51mmol,1当量),并在室温下搅拌30分钟,然后升温至80℃6小时。所述反应通过添加水来淬灭,并用EtOAc(3x50ml)萃取。合并有机物,用水性饱和NaCl洗涤,用MgSO4干燥并浓缩。剩余物在MeCN中研磨,然后通过过滤分离白色固体,获得第一批3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(1.36g,产率36%)。母液经浓缩并在硅胶上通过色谱纯化以获得第二批产物(2.9g,50%纯度,产率40%)。
步骤5:根据方法P1制备3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物1)
向内含3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(1g,3.21mmol,1当量)的MeCN(50ml)和DMF(10ml)溶液添加碳酸钾(532mg,3.85mmol,1.2当量),然后添加碘甲烷(547mg,3.85mmol,1.2当量)。使所述反应在室温搅拌过夜。通过添加水来淬灭所述反应,并用EtOAc(3x50ml)萃取。合并有机物,用水性饱和的NaCl洗涤,用MgSO4干燥并浓缩。剩余物在硅胶柱上通过色谱纯化以获得白色固态的3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(906mg,产率85%)。
制备实施例2:根据方法P2的{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁酯(化合物18)向内含3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(60mg,0.184mmol,1当量)的吡啶(2ml)溶液添加丁基胺甲酰氯(50.3mg,0.369mmol,2当量),并搅拌过夜。通过添加水来淬灭所述反应,并浓缩至干。将剩余物收集在EtOAc中并添加0.5ml 1N NaOH。所述溶液通过Chem Elut垫过滤,并用EtOAc洗涤。浓缩后,使剩余物在硅胶上通过色谱纯化以获得{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁酯(60mg,产率75%)。
制备实施例3:根据方法P5的3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物1)和3-[(E)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物25)
步骤1:根据方法P5制备3-苯甲酰基-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物VII-1)
向内含3-苄基-4-甲基-1,2,4-噁二唑-5(4H)-酮(3.87g,20.34mmol,1当量)的乙酸(120ml)溶液添加氧化铬(VI)(6.10g,61.04mmol,3当量),并搅拌过夜。通过添加水来使所述反应淬灭,并用Et2O(3x 50ml)萃取。合并有机物,用水性饱和NaHCO3洗涤,用MgSO4干燥,并浓缩以获得白色固态的3-苯甲酰基-4-甲基-1,2,4-噁二唑-5(4H)-酮(3.85g,产率88%)。
步骤2:根据方法P5制备3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物1)和3-[(E)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物25)
向微波管中的内含3-苯甲酰基-4-甲基-1,2,4-噁二唑-5(4H)-酮(500mg,2.44mmol,1当量)的iPrOH(10ml)溶液添加6-[(氨基氧基)甲基]吡啶-2-胺(340mg,2.44mmol,1当量),然后添加pTSA.H2O(578mg,2.93mmol,1.2当量)。使所述反应在160℃微波处理2小时,然后通过添加水来淬灭,并用EtOAc(3x 50ml)萃取。合并有机物,用水性饱和NaHCO3洗涤,用MgSO4干燥并浓缩。剩余物通过制备型HPLC纯化以获得3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(200mg,25%)和3-[(E)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(62mg,8%)。
制备实施例4:根据方法P1的3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(化合物4)
步骤1:
向内含(2Z)-(羟基亚氨基)(苯基)乙腈(2.5g,17.10mmol,1当量)的100ml乙腈和10ml DMF溶液添加盐酸4-(氯甲基)-1,3-噻唑-2-胺(3.79g,20.52mmol,1.2当量),然后添加碘化钾(283mg,1.71mmol,0.1当量)和碳酸铯(13.37g,41.05mmol,2.4当量)。使所述反应在室温下搅拌过夜。然后蒸发溶剂并使剩余物溶解于EtOAc(100ml)。有机层用H2O洗涤并用MgSO4干燥,然后浓缩。获得白色固态的(2Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)乙腈(4g,产率90%,仅1种肟异构体)。
步骤2:根据方法P1制备(1Z,2Z)-2-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(化合物V-2)
向内含(2Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)乙腈(4.5g,17.42mmol,1当量)的iPrOH/H2O(10/1,110ml)悬液添加盐酸羟胺(3.63g,52.26mmol,3当量)和碳酸钾(7.22g,52.2mmol,3当量)。使所述反应升温至80℃6小时,并蒸发溶剂至3/4。剩余物用EtOAc(3x50ml)萃取并用水性饱和NaCl洗涤。合并有机物,用MgSO4干燥并浓缩以获得白色固态的(1Z,2Z)-2-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(5.86g)。
步骤3:根据方法P1制备3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(化合物24)
向内含(1Z,2Z)-2-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}-N'-羟基-2-苯基乙脒(3g,10.29mmol,1当量)的DMF(50ml)溶液添加CDI(1.66g,10.29mmol,1当量),并在室温下搅拌30分钟,然后升温至80℃6小时。所述反应通过添加水来淬灭并用EtOAc(3x50ml)萃取。合并有机物,用水性饱和NaCl洗涤,用MgSO4干燥并浓缩。剩余物在MeCN中研磨并通过过滤来分离白色固体,获得3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(2.89g,50%纯度,产率43%)。
步骤4:根据方法P1制备3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(化合物4)
向内含3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-1,2,4-噁二唑-5(4H)-酮(2.89g,50%纯度,4.56mmol,1当量)的MeCN(50ml)和DMF(10ml)溶液添加碳酸钾(757mg,5.48mmol,1.2当量),然后添加碘甲烷(778mg,5.48mmol,1.2当量)。使所述反应在室温下搅拌过夜。通过添加水来淬灭所述反应,然后用EtOAc(3x 50ml)萃取。合并有机物,用水性饱和NaCl洗涤,用MgSO4干燥并浓缩。剩余物在硅胶上通过色谱纯化以获得白色固态的3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(930mg,产率61%)。
制备实施例5:根据方法P2的{4-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]-1,3-噻唑-2-基}氨基甲酸丁酯(化合物14)
向内含3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(60mg,0.181mmol,1当量)的吡啶(2ml)溶液添加丁基胺甲酰氯(49.4mg,0.362mmol,2当量)并搅拌过夜。通过添加水来淬灭所述反应,然后浓缩至干。将剩余物收集在EtOAc中,并添加0.5ml 1N NaOH。所述溶液通过Chem Elut垫过滤,并用EtOAc洗涤。浓缩之后,剩余物在硅胶上通过色谱纯化以获得{4-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]-1,3-噻唑-2-基}氨基甲酸丁酯(45mg,产率55%)。
制备实施例6:根据方法P2的叔丁基{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯(化合物21)
向内含3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(100mg,0.307mmol,1当量)的四氢呋喃(5ml)溶液添加三乙胺(0.118mL,1.23mmol,4当量),然后添加二碳酸二叔丁酯(201mg,0.922mmol,3当量)并搅拌过夜。通过添加1N HCl来淬灭所述反应,然后用EtOAc(3x20ml)萃取。合并有机物,用MgSO4干燥并浓缩。将剩余物收集在二氯甲烷中,然后添加三氟乙酸(0.118mL,1.54mmol,5当量)。使所述溶液在室温下搅拌2小时,通过添加水性饱和NaHCO3淬灭,并用EtOAc(3x 20ml)萃取。合并有机物,用MgSO4干燥并浓缩。浓缩之后,剩余物在硅胶上通过色谱纯化以获得{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯(110mg,产率83%)。
制备实施例7:根据方法P6的(2-环己基乙基){6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯(化合物279)
使内含{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯(100mg,0.235mmol,1当量)的N,N-二甲基甲酰胺(2ml)溶液用氢化钠(10mg,0.259mmol,1.1当量)处理,并在室温下搅拌30分钟。然后添加(2-溴乙基)环己烷(67mg,0.353mmol,1.5当量)并搅拌过夜。通过添加水来淬灭所述反应,并用EtOAc(3x 20ml)萃取。合并有机物,用水性饱和NaCl洗涤,用MgSO4干燥并浓缩以获得(2-环己基乙基){6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯(108mg,产率86%),其无需进一步纯化即可用于下一步骤。
制备实施例8:根据方法P7的3-[(Z)-[({6-[(2-环己基乙基)氨基]吡啶-2-基}甲氧基)亚氨基](苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物253)
使内含(2-环己基乙基){6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯(100mg,0.187mmol,1当量)的二氯甲烷(5ml)溶液用三氟乙酸(0.144mL,1.867mmol,10当量)处理,并回流过夜。通过添加饱和水性NaHCO3来淬灭所述反应,并用EtOAc(3x 20ml)萃取。合并有机物,用水性饱和NaCl洗涤,用MgSO4干燥并浓缩。浓缩之后,剩余物在硅胶上通过色谱纯化以获得3-[(Z)-[({6-[(2-环己基乙基)氨基]吡啶-2-基}甲氧基)亚氨基](苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(52mg,产率63%)。
制备实施例9:根据方法P8的3-[(Z)-({[6-(二乙基氨基)吡啶-2-基]甲氧基}亚氨基)(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(化合物197)和4-甲基-3-{(Z)-苯基[({6-[(1-苯基乙基)氨基]吡啶-2-基}甲氧基)亚氨基]甲基}-1,2,4-噁二唑-5(4H)-酮(化合物43)
在氩气下,向内含3-[(Z)-{[(6-氨基吡啶-2-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(200mg,0.615mmol,1当量)的二氯甲烷(2.5ml)溶液添加苯乙酮(73.9mg,0.615mmol,1当量),然后添加氯化钛(IV)(0.615mL,0.615mmol,1当量),并在室温下搅拌1小时。然后添加三乙酰氧基硼氢化钠(651.5mg,3.07mmol,5当量)并在室温下搅拌过夜。使粗制混合物通过Chem Elut垫过滤并用EtOAc洗涤。浓缩之后,剩余物在硅胶上通过色谱纯化以获得3-[(Z)-({[6-(二乙基氨基)吡啶-2-基]甲氧基}亚氨基)(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(30mg,产率11%)和4-甲基-3-{(Z)-苯基[({6-[(1-苯基乙基)氨基]吡啶-2-基}甲氧基)亚氨基]甲基}-1,2,4-噁二唑-5(4H)-酮(60mg,产率23%)。
制备实施例10:根据方法P10的2-甲基戊烷-2-基{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯(化合物233)
向内含3-[(Z)-{[(2-氨基-1,3-噻唑-4-基)甲氧基]亚氨基}(苯基)甲基]-4-甲基-1,2,4-噁二唑-5(4H)-酮(120mg,0.369mmol,1当量)的乙腈(3ml)溶液添加4-氟苯基氯甲酸酯(70.8mg,0.406mmol,1.1当量),然后添加吡啶(0.030mL,0.369mmol,1当量)并在室温下搅拌2小时。然后添加2-甲基-4-戊烷-2-醇(0.050mL,0.406mmol,1.1当量)并使所得混合物回流5小时。浓缩之后,剩余物在硅胶上通过色谱纯化以获得透明油状的2-甲基戊烷-2-基{6-[({[(Z)-(4-甲基-5-氧代-4,5-二氢-1,2,4-噁二唑-3-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸酯(105mg,产率59%)。
Claims (16)
1.一种式(I)化合物,及其盐,或其(E)和(Z)异构体,以及(E)和(Z)异构体的混合物,
其中
X1代表氢原子;C1-C8-烷基,其为未经取代的或经一个或更多个选自卤素原子和氰基的基团或原子取代;未经取代的C2-C8-烯基;未经取代的C2-C8-炔基;
·A选自下组:A1~A2:
其中
-Z1代表氨基基团;C1-C8-烷基氨基,其为未经取代的或经一个或更多个选自芳基、C3-C8-环烷基、苄氧基的基团取代,其中芳基为苯基;未经取代的二-C1-C8-烷基氨基;或式QC(=U)NRa的基团
其中:
-Q代表C1-C8-烷基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;C1-C8-烷基;C3-C8-环烷基;C1-C8-烷氧基;芳基,其为未经取代的,其中芳基为苯基或萘基;苯氧基,其为未经取代的;
C3-C8-环烷基,其为未经取代的或经一个或更多个如下的基团或原子取代:
卤素原子;未经取代的C1-C8-烷基;未取代的芳基,其中芳基为苯基;
C2-C8-烯基,其为未经取代的或经一个或更多个C1-C8-烷基取代;
未经取代的C2-C8-炔基;
C1-C8-烷氧基,其为未经取代的或经一个或更多个如下的基团或原子取代:
卤素原子;氰基;C1-C8-烷基;C1-C8-烷氧基;C3-C8-环烷基;芳基,其为未经取代的,其中芳基为苯基;
未经取代的C2-C8-烯基氧基;
C2-C8-炔基氧基,其为未经取代的或经一个或更多个C1-C8-烷基取代;
芳基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;C1-C8-烷基;C1-C8-烷氧基;苯氧基,其中芳基为苯基;
未经取代的C3-C8-环烷氧基;
芳氧基,其为未经取代的或经一个或更多个卤素原子取代,其中芳基为苯基;
-U代表氧原子;
-Ra代表氢原子;C1-C8-烷基,其为未经取代的或经C3-C8-环烷基取代;芳氧基羰基,其经卤素原子取代,其中芳基为苯基;未经取代的C1-C8-烷氧基羰基;
-Z2、Z3和Z4独立地代表氢原子;
·Y1代表氢原子;
·Y2代表氢原子、卤素原子、未经取代的C1-C8-烷氧基或未经取代的C1-C8-烷基;
·Y3代表氢原子、卤素原子、未经取代的C1-C8-烷氧基或未经取代的C1-C8-烷基;
·Y4代表氢原子;
·Y5代表氢原子。
2.如权利要求1所述的化合物,其特征在于,X1代表氢原子;C1-C8-烷基,其为未经取代的或经一个或更多个选自卤素原子和氰基的基团或原子取代;或未经取代的C2-C8-烯基。
3.如权利要求2所述的化合物,其特征在于,X1代表氢原子、甲基基团或乙基基团。
4.如权利要求1所述的化合物,其特征在于,A代表A1。
5.如权利要求1所述的化合物,其特征在于,Z1代表氨基基团或式QC(=U)NRa的基团。
6.如权利要求1所述的化合物,其特征在于,Ra代表氢原子;或C1-C8-烷基,其为未经取代的或经C3-C8-环烷基取代。
7.如权利要求1所述的化合物,其特征在于,Q代表
C1-C8-烷基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;C1-C8-烷基;C3-C8-环烷基;C1-C8-烷氧基;芳基,其为未经取代的,其中芳基为苯基或萘基;苯氧基,其为未经取代的;
C3-C8-环烷基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;未经取代的C1-C8-烷基;未经取代的芳基,其中芳基为苯基;
未经取代的C2-C8-炔基;
C1-C8-烷氧基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;氰基;C1-C8-烷基;C1-C8-烷氧基;C3-C8-环烷基;芳基,其为未经取代的,其中芳基为苯基;
未经取代的C2-C8-烯基氧基;
C2-C8-炔基氧基,其为未经取代的或经一个或更多个C1-C8-烷基取代;
芳基,其为未经取代的或经一个或更多个如下的基团或原子取代:卤素原子;C1-C8-烷基;C1-C8-烷氧基;苯氧基,其中芳基为苯基;
未经取代的C3-C8-环烷氧基。
8.一种式(VII)的化合物
其中Y1、Y2、Y3、Y4、Y5如权利要求1~7中任一项所定义,并且X1代表C1-C8-烷基,其为未经取代的或经一个或更多个选自卤素原子和氰基的基团或原子取代。
9.一种杀真菌性组合物,所述组合物包含作为活性成分的有效量的如权利要求1~7中任一项所述的式(I)化合物和农学上可接受的担体、载体或填料。
10.如权利要求9所述的杀真菌性组合物,所述组合物包含选自下组的至少一种其它活性成分:杀昆虫剂、引诱剂、消毒剂、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、生物制剂和化学信息素。
11.一种控制作物的植物病原性真菌的方法,其特征在于,将农学上有效且基本上无植物毒性的量的如权利要求1~7中任一项所述的化合物或者如权利要求9或10所述的组合物施用至植物生长或者能够生长的土壤,施用到植物叶子和/或植物果实上,或者施用到植物种子上。
12.如权利要求1~7中任一项所述的式(I)化合物用于防控植物病原性有害真菌的用途。
13.制备用于防控植物病原性有害真菌的组合物的方法,其特征在于,使如权利要求1~7中任一项所述的式(I)的化合物与填充剂和/或表面活性剂混合。
14.如权利要求1~7中任一项所述的式(I)化合物用于处理转基因植物的用途。
15.如权利要求1~7中任一项所述的式(I)化合物用于处理种子的用途。
16.如权利要求15所述的用途,其特征在于,所述种子是转基因植物的种子。
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TWI549951B (zh) | 2016-09-21 |
CN103874681A (zh) | 2014-06-18 |
JP6002225B2 (ja) | 2016-10-05 |
EP2755949B1 (en) | 2015-10-21 |
MX347562B (es) | 2017-05-03 |
EP2755949A1 (en) | 2014-07-23 |
MX2014002833A (es) | 2014-05-28 |
TW201317232A (zh) | 2013-05-01 |
US9090600B2 (en) | 2015-07-28 |
KR20140067114A (ko) | 2014-06-03 |
KR101978006B1 (ko) | 2019-05-13 |
JP2014526452A (ja) | 2014-10-06 |
WO2013037717A1 (en) | 2013-03-21 |
US20140349848A1 (en) | 2014-11-27 |
BR112014005471A2 (pt) | 2017-03-28 |
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