CN117800956A - 苯并杂环酰肼腙类化合物及制备方法和杀菌剂应用 - Google Patents
苯并杂环酰肼腙类化合物及制备方法和杀菌剂应用 Download PDFInfo
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- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
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- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 239000004560 ultra-low volume (ULV) liquid Substances 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms six-membered rings
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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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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- A—HUMAN NECESSITIES
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
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- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur 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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- 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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Abstract
本发明公开了苯并杂环酰腙类化合物及制备方法和杀菌剂应用。具体地,涉及式I所示的化合物,以及所述化合物作为农用杀菌剂的用途。
Description
技术领域
本发明涉及苯并杂环酰腙类化合物及其杂取代的类似物作为农用杀菌剂,它们的制备方法以及它们作为杀菌剂的用途,特别是以杀菌剂组合物的形式,以及用这些化合物或它们的组合物来控制植物的植物病原真菌的方法。
背景技术
植物病害一直是限制农作物安全生产的主要因素之一,病害发生时不仅会造成减产,而且还要严重影响农作物的品质,杀菌剂的使用大大减少了由植物病害引起的经济损失,为粮食安全供应提供了重要保障。杀菌剂的使用给人们带来巨大经济效益和社会效益的同时,也带来了许多的负面影响。由于杀菌剂的不合理使用,使得病原物对现代杀菌剂的抗性日趋严重,也对非靶标生物造成了一定影响,给环境带来了巨大压力。随着人们对健康饮食的重视,以及环保意识的增强,创制“高效、低毒、安全”的绿色杀菌剂已成为农药研究领域的重点研究方向。
苯并杂环作为一种广泛存在于天然产物中的片段,本身具有多种特殊的生物活性,目前在医学、农学、生物学领域有着广泛的应用。酰腙骨架被广泛用作酰胺的理想生物等排体,其比生物体中的酰胺部分能更有效地与各种生物靶标结合,是开发新的农用化学品的潜在片段。
发明内容
本发明涉及农药杀菌剂领域,公开了式(Ⅰ)化合物,其光学异构体、顺反异构体或其农药学上可接受的盐,及制备方法和杀菌剂应用。
本发明第一方面,提供了一种一种式(I)化合物,其光学异构体、顺反异构体或其农药学上可接受的盐:
式中:
A选自下组:取代或未取代的苯环或萘环;取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-10元杂环或杂芳环;
G为取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-10元杂环或杂芳环;
其中,取代指所述基团独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基X取代:
X表示氢(H)、卤素(如F、Cl、Br或I)、羟基、巯基、硝基、羧基、酯基、氰基、独立地任选一个或多个取代基取代的C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷硫基、C1-C8卤代烷硫基、C1-C8烷胺基、C1-C8二烷基胺基、C1-C8卤代烷胺基、C1-C8卤代二烷基胺基、C3-C8环烷基、C2-C8烯基、C2-C8卤代烯基、C2-C8烯氧基、C2-C8炔基、C5-C7环烯基、C1-C8烷基亚硫酰基、C1-C8亚硫酰基烷基、C1-C8烷基磺酰基、C1-C8磺酰基烷基、C1-C8烷基羰基、C1-C8羰基烷基、C1-C6烷氧基羰基、C1-C8羰基烷氧基、C1-C8烷胺基羰基、C1-C8羰基烷胺基、C1-C8烷胺基硫代羰基、C1-C8硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、、C1-C6三烷基甲硅烷基、C1-C6硼酯基、5-7元非芳杂环基;
或者X独立地为取代或未取代地:苯基、苄基、苯甲酰基、偶氮芳基、苯氧基5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环系统;
其中,所述取代指X独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基取代:氢、卤素、羟基、巯基、氰基、硝基、氧代(=O)、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷胺基、C1-C6二烷基胺基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯氧基、C2-C6炔基、C5-C7环烯基、C1-C6烷基亚硫酰基、C1-C6亚硫酰基烷基、C1-C6烷基磺酰基、C1-C6磺酰基烷基、C1-C6烷基羰基、C1-C6羰基烷基、C1-C6烷氧基羰基、C1-C6羰基烷氧基、C1-C6烷胺基羰基、C1-C6羰基烷胺基、C1-C6烷胺基硫代羰基、C1-C6硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C1-C6三烷基甲硅烷基、C1-C6硼酯基、苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环;
Q表示苯环上0-4个(优选地为1、2、3或4个)取代基,且各Q独立任选地选自下组:氢(H)、卤素(包括F、Cl、Br或I,下同)、羟基、巯基、硝基、羧基、酯基、氰基或独立地任选一个或多个取代基取代的C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷硫基、C1-C8卤代烷硫基、C1-C8烷胺基、C1-C8二烷基胺基、C1-C8卤代烷胺基、C1-C8卤代二烷基胺基、C3-C8环烷基、C2-C8烯基、C2-C8卤代烯基、C2-C8烯氧基、C2-C8炔基、C5-C7环烯基、C1-C8烷基亚硫酰基、C1-C8亚硫酰基烷基、C1-C8烷基磺酰基、C1-C8磺酰基烷基、C1-C8烷基羰基、C1-C8羰基烷基、C1-C8烷氧基羰基、C1-C8羰基烷氧基、C1-C8烷胺基羰基、C1-C8羰基烷胺基、C1-C8烷胺基硫代羰基、C1-C8硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C1-C6三烷基甲硅烷基、C1-C6硼酯基、5-7元非芳杂环基;
或者各Q独立地为取代或未取代地:苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环系统;且
其中所述取代指Q独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基取代:氢、卤素、羟基、巯基、氰基、硝基、氧代(=O)、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷胺基、C1-C6二烷基胺基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯氧基、C2-C6炔基、C5-C7环烯基、C1-C6烷基亚硫酰基、C1-C6亚硫酰基烷基、C1-C6烷基磺酰基、C1-C6磺酰基烷基、C1-C6烷基羰基、C1-C6羰基烷基、C1-C6烷氧基羰基、C1-C6羰基烷氧基、C1-C6烷胺基羰基、C1-C6羰基烷胺基、C1-C6烷胺基硫代羰基、C1-C6硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C3-C6三烷基甲硅烷基、C2-C6硼酯基、苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环。
在另一优选例中,A选自下组:取代或未取代的苯环、或取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5元或6元杂环或杂芳环,优选地,A选自下组:
在另一优选例中,A为具有1或2个N原子的5或6元杂芳环。
在另一优选例中,G为取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-6元杂环或杂芳环;优选地,G选自下组:
在另一优选例中,G是取代或未取代的:吡喃、吡啶或呋喃,如下图所示,其中取代基X如权利要求1中X定义。
其中,G环最优选为4氢-吡喃,1,4-二氢吡啶和2,3-二氢呋喃。
在另一优选例中,所述式I化合物的结构如式II,III或式IV所示,
其中A和Q如权利要求1定义。
在另一优选例中,A为3-(二氟甲基)-1-甲基-1H-吡唑基。
在另一优选例中,式I化合物结构如式V;
最优选的Q为单卤素取代或者双卤素基团。
在另一优选例中,所述化合物是表2所示的化合物1-133。
在另一优选例中,A、G和Q(或)独立任选地为本发明的具体实施例中对应的基团,尤其是表2中的那些。
本发明第二方面,提供了一种农药组合物,包括如本发明第一方面所述的式(I)化合物,其光学异构体、顺反异构体或其农药学上可接受的盐;和农药学上可接受的载体。
在另一优选例中,所述农药组合物中,所述式(I)化合物的含量为0.01-99.99wt%,较佳地1-99wt%。
本发明第三方面,提供了一种如本发明第一方面所述的式(I)化合物的制备方法,所述方法包括步骤:在惰性溶剂中,将化合物(VI)和化合物(VII)进行反应,从而得到式(I)化合物
本发明第四方面,提供了一种如本发明第一方面所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐,或如本发明第二方面所述的农药组合物的用途,用于防治植物病原菌及相关疾病或制备杀菌剂组合物。
本发明第五方面,提供了一种防治作物的植物病原菌及相关疾病的方法,包括步骤:将如本发明第一方面所述的化合物或如本发明第二方面所述的农药组合物施用到植物在其中生长或能够在其中生长的土壤中,或施用到植物的植株上,如根、茎、叶子、果实和/或种子上,从而防治所述植物病原菌及相关疾病。
应理解,在本发明范围内中,本发明的上述各技术特征和在下文(如实施例)中具体描述的各技术特征之间都可以互相组合,从而构成新的或优选的技术方案。限于篇幅,在此不再一一累述。
具体实施方式
本发明人经过广泛而深入的研究,通过大量筛选和测试,提供了一类结构新颖的农用杀菌剂,且本发明的化合物具有优异的杀菌效果。在此基础上完成了本发明。
术语
除非另有定义,否则本文中所用的全部技术术语和科学术语均具有如本发明所属领域普通技术人员通常理解的相同含义。
如本文所用,术语“含有”或“包括(包含)”可以是开放式、半封闭式和封闭式的。换言之,所述术语也包括“基本上由…构成”、或“由…构成”。
在本发明中,术语“卤素”指氟、氯、溴或碘。
术语“卤代”指被相同或不同的一个或多个上述卤原子取代的基团,例如二氟甲基、五氯乙基、七氟异丙基或类似基团。
术语“C0–C8”、“C1–C8”、“C2–C8”、“C1–C6”、“C2–C6”、C3-C6等是指所述基团具有指定碳原子数,其各自独立地可以具有指定范围内的碳原子,如0、1、2、3、4、5、6、7或8个碳原子,依此类推。术语“5-10元”、“5-7元”、“3-6元”等是指所述基团具有指定个数的环原子,其各自独立地可以具有指定范围内的环原子,如3、4、5、6、7、8、9或10个环原子,依此类推。
术语“C1–C8烷基”是指具有1–8个碳原子的直链或支链烷基,例如C1–C6或C1–C4烷基,典型地烷基包括甲基、乙基、异丙基、叔丁基或类似基团。本发明中烷基可作为其他基团的一部分,如卤代烷基,烷氧基、烷胺基等,如未特别说明,其定义如此所述。
术语“C2–C8烯基”是指具有2–8个碳原子的直链或支链的烯基,例如C2–C6或C2–C4烯基,典型地烯基包括乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基或类似基团。
术语“C2–C8炔基”是指具有2–8个碳原子的直链或支链的炔基,例如C2–C6或C2–C4炔基,典型地烯基包括乙炔基、丙炔基或类似基团。
术语“C3–C8环烷基”指具有3–8个碳原子的环状烷基,例如环丙基、环丁基、环戊基、环己基、环庚基或类似基团。
术语“5–10元杂环基”是指包含1-4个(优选地2或3个)环杂原子(例如N,O或S)的5–10元非芳环状基团,例如5-7元杂环基,典型的杂芳基包括吗啉基、六氢异吲哚基、四氢呋喃基、四氢吡咯基等。通常,杂环包含不超过4个氮、不超过2个氧和/或不超过2个硫。除非另外指明,杂环可以是饱和的、部分不饱和的或完全不饱和的环。其中,氮原子或硫原子可以被氧化,氮原子也可以被季铵化。
术语“C6–C10芳基”是指环上不含杂原子的具有6至10个碳原子的芳香族环基,例如苯基、萘基等。
术语“5–10元杂芳基”是指环上含有1-4个(优选地2或3个)杂原子(例如N,O或S)的5–10元杂芳族环基,例如5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环系统,典型的杂芳基包括吡咯基、呋喃基、噻吩基、吡唑基、噻唑基、咪唑基、噁唑基、异噁唑基、吡啶基、吡喃基、哒嗪基、嘧啶基、吡嗪基、苯并吲哚、苯并呋喃、苯并咪唑基等。
术语“C1–C8烷氧基”是指具有1–8个碳原子的直链或支链烷氧基,例如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基或类似基团。烯氧基、炔氧基、环烷基氧基、芳氧基、杂芳氧基依此类推。
术语“C1–C8烷硫基”是指具有1–8个碳原子的直链或支链烷硫基,例如甲硫基、乙硫基、异丙硫基、叔丁硫基或类似基团。烯硫基、炔硫基、环烷基硫基、芳硫基、杂芳硫基依此类推。
术语“C1–C8烷胺基”是指具有一个1–8个碳原子的直链或支链烷胺基,例如甲胺基、乙胺基、异丙胺基、叔丁胺基或类似基团。烯胺基、炔胺基、环烷基胺基、芳胺基、杂芳胺基依此类推。
术语“C1–C8烷胺基”是指具有两个1–8个碳原子的直链或支链烷胺基,例如二甲胺基、二乙胺基、二异丙胺基、二叔丁胺基或类似基团。
术语“C1-C8烷基亚硫酰基”指-C1-C8烷基-(S=O)-C0-C8烷基。
术语“C1-C8亚硫酰基烷基”指-(S=O)-C1-C8烷基。
术语“C1-C8烷基磺酰基”指-C1-C8烷基-(S=O)2-C0-C8烷基。
术语“C1-C8磺酰基烷基”指-(S=O)2-C1-C8烷基。
术语“C1-C8烷基羰基”指-C1-C8烷基-(C=O)-C0-C8烷基。
术语“C1-C8羰基烷基”指-(C=O)-C1-C8烷基。
术语“酯基”指-O(C=O)-C1-C8烷基。
术语“C1-C8烷氧基羰基”指-C1-C8烷基-O-(C=O)-C0-C8烷基。
术语“C1-C8羰基烷氧基”指-C1-C8烷基-(C=O)-O-C0-C8烷基。
术语“C1-C8烷胺基羰基”指-C1-C8烷基-NH-(C=O)-C0-C8烷基。
术语“C1-C8羰基烷胺基”指-C1-C8烷基-(C=O)-NH-C0-C8烷基。
术语“C1-C8烷胺基硫代羰基”指-C1-C8烷基-NH-(C=S)-C0-C8烷基。
术语“C1-C8硫代羰基烷胺基”指-C1-C8烷基-(C=S)-NH-C0-C8烷基。
术语“C3-C6环烷氧基”指具有一个3–6个碳原子的环烷氧基。例如: 或类似基团。
术语“C3-C6环烷氨基”指具有一个3–6个环碳原子的环烷氨基。例如: 或类似基团。
术语“偶氮芳基”指-N=N-芳基,如-N=N-苯基。
术语“C1-C6三烷基甲硅烷基”指具有三个具有1-6个碳原子的直链或支链烷基的甲硅烷基,例如三甲基硅烷类似基团。
术语“C1-C6硼酯基”指具有两个1-6个碳原子的直链或支链烷基的硼酯基,例如二甲基硼酯基,二乙基硼酯基类似基团。
术语Me指代甲基,Et指代乙基,i-Pr指代异丙基,t-Bu指代叔丁基,Ac指代乙酰基,Bn指代苄基。
如本文所述,术语“多个”是指两个或以上,如2、3、4、5或6。
如本文所用,术语“取代”或“取代的”是指基团上的一个或多个氢被选自指定的取代基取代,条件是不超过指定的原子的正常价,并且取代产生的化合物是稳定的,即可以分离,表征和进行生物活性测试的化合物。
如未特别说明,所述取代,所述取代指各基团上的一个或多个H独立地被选自取代或未取代的述A组基团取代:氢、卤素、羟基、巯基、氰基、硝基、氧代(=O)、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷胺基、C1-C6二烷基胺基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯氧基、C2-C6炔基、C5-C7环烯基、C1-C6烷基亚硫酰基、C1-C6亚硫酰基烷基、C1-C6烷基磺酰基、C1-C6磺酰基烷基、C1-C6烷基羰基、C1-C6羰基烷基、C1-C6烷氧基羰基、C1-C6羰基烷氧基、C1-C6烷胺基羰基、C1-C6羰基烷胺基、C1-C6烷胺基硫代羰基、C1-C6硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C1-C6三烷基甲硅烷基C1-C6硼酯基、苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环。
活性成分
本发明提供了一种式(I)化合物,其光学异构体、顺反异构体或其农药学上可接受的盐作为本发明的活性成分。
其中,A、G和Q如上定义。
本发明中的化合物可能形成的盐也是属于本发明的范围。除非另有说明,本发明中的化合物被理解为包括其盐类。在此使用的术语“盐”,指用无机或有机酸和碱形成酸式或碱式的盐。此外,当本发明中的化合物含一个碱性片段时,它包括但不限于吡啶或咪唑,含一个酸性片段时,包括但不限于羧酸,可能形成的两性离子(“内盐”)包含在术语“盐”的范围内。药学上可接受的(即无毒,生理可接受的)盐是首选,虽然其他盐类也有用,例如可以用在制备过程中的分离或纯化步骤。本发明的化合物可能形成盐,例如,化合物I与一定量如等当量的酸或碱反应,在介质中盐析出来,或在水溶液中冷冻干燥得来。
本发明中的化合物含有的碱性片段,包括但不限于胺或吡啶或咪唑环,可能会和有机或无机酸形成盐。可以成盐的典型的酸包括醋酸盐(如用醋酸或三卤代醋酸,如三氟乙酸)、己二酸盐、藻朊酸盐、抗坏血酸盐、天冬氨酸盐、苯甲酸盐、苯磺酸盐、硫酸氢盐、硼酸盐、丁酸盐、柠檬酸盐、樟脑盐、樟脑磺酸盐、环戊烷丙酸盐、二甘醇酸盐、十二烷基硫酸盐、乙烷磺酸盐、延胡索酸盐、葡庚糖酸盐、甘油磷酸盐、半硫酸盐、庚酸盐、己酸盐、盐酸盐、氢溴酸盐、氢碘酸盐、羟基乙磺酸盐(如,2-羟基乙磺酸盐)、乳酸盐、马来酸盐、甲磺酸盐、萘磺酸盐(如,2-萘磺酸盐)、烟酸盐、硝酸盐、草酸盐、果胶酸盐、过硫酸盐、苯丙酸盐(如3-苯丙酸盐)、磷酸盐、苦味酸盐、新戊酸盐、丙酸盐,水杨酸盐、琥珀酸盐、硫酸盐(如与硫酸形成的)、磺酸盐、酒石酸盐、硫氰酸盐、甲苯磺酸盐如对甲苯磺酸盐、十二烷酸盐等等。
本发明的某些化合物可能含有的酸性片段,包括但不限于羧酸,可能会和各种有机或无机碱形成盐。典型的碱形成的盐包括铵盐、碱金属盐如钠、锂、钾盐,碱土金属盐如钙、镁盐和有机碱形成的盐(如有机胺),如苄星、二环已基胺、海巴胺(与N,N-二(去氢枞基)乙二胺形成的盐)、N-甲基-D-葡糖胺、N-甲基-D-葡糖酰胺、叔丁基胺,以及和氨基酸如精氨酸、赖氨酸等等形成的盐。碱性含氮基团可以与卤化物季铵盐,如小分子烷基卤化物(如甲基、乙基、丙基和丁基的氯化物、溴化物及碘化物),二烷基硫酸盐(如,硫酸二甲酯、二乙酯,二丁酯和二戊酯),长链卤化物(如癸基、十二烷基、十四烷基和十四烷基的氯化物、溴化物及碘化物),芳烷基卤化物(如苄基和苯基溴化物)等等。
本发明的化合物还包括其晶型,溶剂合物,如水合物。
如本文所用,术语“溶剂合物”是指本发明化合物与溶剂分子配位形成特定比例的配合物。
如本文所用,术语“水合物”是指本发明化合物与水进行配位形成的配合物,如一水合物。
本发明中的化合物、盐或溶剂合物,可能存在的互变异构形式(例如酰胺和亚胺醚)。所有这些互变异构体都是本发明的一部分。
本发明的某些化合物可能存在于特定的几何或立体异构体形式。本发明涵盖所有的化合物,包括其顺式和反式异构体、R和S对映异构体、非对映体、(D)型异构体、(L)型异构体、外消旋混合物和其它混合物。另外不对称碳原子可表示取代基,如烷基。所有异构体以及它们的混合物,都包涵在本发明中。
按照本发明,同分异构体的混合物含有异构体的比率可以是多样的。例如,在只有两个异构体的混合物可以有以下组合:50:50,60:40,70:30,80:20,90:10,95:5,96:4,97:3,98:2,99:1,或100:0,异构体的所有比率都在本发明范围之内。本专业内一般技术人员容易理解的类似的比率,及为更复杂的异构体的混合物的比率也在本发明范围之内。
如果要设计一个本发明的化合物特定的对映体的合成,它可以不对称合成制备,或用手性辅剂衍生化,将所产生的非对映混合物分离,再除去手性辅剂而得到纯的对映体。另外,如果分子中含有一个碱性官能团,如氨基酸,或酸性官能团,如羧基,可以用合适的光学活性的酸或碱的与之形成非对映异构体盐,再通过分离结晶或色谱等常规手段分离,然后就得到了纯的对映体。
本发明还包括同位素标记的化合物,等同于原始化合物在此公开。不过实际上对一个或更多的原子被与其原子量或质量序数不同的原子取代通常会出现。可以列为本发明的化合物同位素的例子包括氢,碳,氮,氧,磷,硫,氟和氯同位素,分别如2H、3H、13C、11C、14C、15N、18O、17O、31P、32P、35S、18F和36Cl。本发明中的化合物,或对映体,非对映体,异构体,或药学上可接受的盐或溶剂化物,其中含有上述化合物的同位素或其他同位素原子都在本发明的范围之内。本发明中某些同位素标记化合物,例如3H和14C的放射性同位素也在其中,在药物和底物的组织分布实验中是有用的。氚,即3H和碳-14,即14C,它们的制备和检测比较容易。是同位素中的首选。此外,较重同位素取代如氘,即2H,由于其很好的代谢稳定性在某些疗法中有优势,例如在体内增加半衰期或减少用量,因此,在某些情况下可以优先考虑。同位素标记的化合物可以用一般的方法,通过用易得的同位素标记试剂替换为非同位素的试剂,用批露在示例中的方案可以制备。
在另一优选例中,式I所示化合物为选自以下的化合物:
用途
另一方面,本发明还涉及含有上述式(I)化合物、其光学异构体、顺反异构体或其农药学上可接受的盐作为活性成分的农药组合物。
本发明的活性成分具有光谱杀菌活性,因此,所述农用组合物可用于防治植物病原菌及相关疾病或制备杀菌剂组合物,将其施用到植物在其中生长或能够在其中生长的土壤中,或施用到植物的植株上,能够有效防治(如杀灭,减少,抑制)作物的植物病原菌以及所述病原菌导致的相关疾病或症状。
优选地,所述农药组合物中,所述式(I)化合物是有效且非植物毒性量的。“有效且非植物毒性量”的表达方式指本发明组合物的量足以控制或破坏存在于或易于出现在作物上的真菌,而该剂量并不会使所述作物产生任何可以观察到的植物毒性症状。该量根据以下因素可在很宽的范围内变化:要控制的真菌、作物的类型、气候条件和包含在本发明的杀菌组合物中的化合物。该量可通过系统性田间试验来确定,这在本领域技术人员的能力范围内。
因此,依据本发明,提供一种杀菌组合物,该组合物包含有效量的上述式(I)化合物作为活性组分以及农业上可接受的担体、载体或填料。
依据本发明,术语“担体”表示天然或合成的有机或无机化合物,它与通式(I)的活性化合物组合或联合使用,使活性化合物更容易施用,特别是施用到植物各部分上。因比,此担体通常是惰性的,并且应该是农业上可接受的。担体可为固体或液体。合适的担体的例子包括粘土、天然或合成的硅酸盐、氧化硅、树脂、蜡、固体肥料、水、醇、有机溶剂、矿物油和植物油以及它们的衍生物。也可以使用这些担体的混合物。
依据本发明的组合物也可以包含其它的组分。具体地,所述组合物还可包含表面活性剂。表面活性剂可为离子或非离子型乳化剂、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(alky1 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并且当施用的媒介试剂是水时,至少一种表面活性剂的存在通常是至关重要的。较佳地,以组合物的重量计,表面活性剂的含量为5重量%至40重量%。
本发明的组合物可以各种形式使用,诸如气溶胶分散剂、胶囊悬浮剂(capsulesuspension)、冷雾浓缩剂、可撒粉剂、可乳化的浓缩剂、水包油乳剂、油包水乳剂、微囊粒剂、细粒剂、种子处理用可流动的浓缩剂、气体制剂(在压力下)、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、油可混溶性可流动的浓缩剂、油可混溶液体、糊剂、植物棒剂、干种子处理用粉剂、农药包衣的种子、可溶性浓缩剂、可溶性粉剂、种子处理用溶液、悬浮浓缩剂(可流动的浓缩剂)、超低量(ULV)液体、超低量(ULV)悬浮剂、水可分散粒剂或片剂、浆液处理用水可分散性粉剂、水溶性粒剂或片剂、种子处理用水溶性粉剂和可润湿性粉剂。这些组合物不仅包括通过合适的设备如喷雾或撒粉设备施用到待处理的植物或种子上的现成组合物,还包括在施用到作物之前必须稀释的浓缩商品组合物。
依据本发明的化合物还可与一种或多种以下物质混合:杀虫剂、杀菌剂、杀细菌剂、引诱剂、杀螨剂或信息素活性物质或其它有生物活性的化合物。这样得到的混合物通常且有广谱的活性。与其杀菌化合物的混合物尤其有利。
本发明的通式(I)的化合物和杀菌组合物可用来治疗性或预防性地控制植物或作物的植物病原菌。
因此,依据本发明的另一方面,本发明还提供了一种治疗性或预防性地控制植物或农作物植物病原菌的方法,该方法的特征在于将本发明的通式(I)的化合物或杀菌组合物施用到种子、植物或植物的果实或者正在生长或需要生长植物的土壤中。
本发明的处理方法还可用于处理繁殖材料如块茎或根茎,并且可用于处理种子、幼苗或移植(pricking out)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如有关植物的干、茎或梗、叶子、花和果实。
依据本发明,所有植物和植物部分都进行处理。植物是指所有植物和植物群体,例如优良和不良野生植物、培育植物和植物品种(无论是否被植物品种或植物培育者权利保护)。培育植物和植物品种可以是通过常规繁殖和培育方法得到的植物,这些方法可得到一种或多种生物技术方法的辅助或补充,例如使用双单倍体,原生质体融合,随机和定向诱变,分子或遗传标记,或利用生物工程和遗传工程方法。植物部分是指植物的所有地上和地下部分以及器官,例如芽、叶、花和根,诸如树叶、针叶、茎、树枝、花、子实体、果实和种子以及根,球茎和根茎。作物和无性繁殖及有性繁殖材料,例如插条、球茎、根茎、纤匐枝和种子也属于植物部分。
在可用本发明的方法保护的植物中,包括主要的大田作物,例如谷物,大豆,棉花,芸苔属含油种子(Brassica oilseeds),诸如甘蓝型油菜(Brassica napus)(例如柯罗纳(canola),芜青(Brassica rapa),褐芥菜(B.juncea)和埃塞俄比亚芥(Brassicacarinata),稻,小麦,糖甜菜,甘蔗,燕麦,黑麦,大麦,黍,小黑麦,亚麻,葡萄藤,各种水果和各种植物分类的蔬菜,诸如蔷薇科(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.)、山毛样科(Fagaceae sp.)、桑科(Moraceae sp.)、木犀科(0leaceae sp.)、猕猴桃科(Actinidaceaesp.)、樟科(Lauraceae sp.)、芭蕉科(Musaceae sp.)(例如香蕉树和香蕉栽培物(plantings))、茜草科(Rubiaceae sp.)(例如咖啡)、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,马铃薯,胡椒,茄子)、百合科(Liliaceae sp.)、菊科(Compositiae sp.)(例如莴,朝鲜蓟和菊-包括根菊苣(root chicory),苣草或普通菊苣(common chicory))、伞形科(Umbelliferae sp.)(例如胡萝卜,荷兰芹,芹菜和块根芹菜)、葫芦科(Cucurbitaceae sp.)(例如黄瓜-包括小黄瓜,南瓜,西瓜,葫芦和甜瓜)、葱科(A1liaceaesp.)(例如洋葱和韭葱),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,白菜,茎蓝,小红萝卜,辣根,水芹,大白菜),豆科(Leguminosae sp.)(例如花生,豌豆和豆类-诸如蔓菜豆和蚕豆),藜科(Chenopodiaceaesp.)(例如饲用甜菜,若菜(spinach beet),菠菜,甜菜根)、锦葵科(Malvaceae)(例如秋葵)、天门冬科(Asparagaceae)(例如芦笋)、园艺作物和森林作物;观赏植物;以及这些作物的遗传修饰的同系物。
根据植物物种或植物品种以及它们的场所和生长环境(土壤、气候、生长期、饮食),依据本发明的处理也可能产生超加(“协同”)效应。因此,例如,减少可依据本发明使用的活性化合物和组合物的施用率和/或拓宽其活性范围和/或增加其活性,有可能获得以下效果:更好的植物生长,对高温或低温的耐受性增加,对干早或水或土壤盐含量的耐受性增加,开花性能提高,更容易收获,加快的成熟,更高的收获率,更大的果实,更高的植物高度,叶子的颜色更绿,开花更早,收获的产品的品质或营养价值更高,果实中糖浓度更高,收获的产品的储存稳定性和/或加工性更佳,这些益处超过了实际预估的效应。
在某些施用率下,依据本发明的活性化合物组合还可能在植物中产生加强效应。因此,它们也适用于动员植物的防御系统来抵抗不利的微生物的进攻。如果合适,这种作用可能是依据本发明的组合例如在抵抗真菌方面活性增强的原因之一。在本申请上下文中,植物加强(抗性诱导)物质应理解为是指能以某种方式刺激植物的防御系统从而在随后被不利的微生物接种时经过处理的植物对这些不利的微生物表现出明显的抵抗性的物质或物质的组合。在此情况中,不利的微生物应理解为是指植物病原真菌、细菌和病毒。因此,依据本发明的物质可用于保护植物,使其在经过处理后的一段时间内能抵抗上述病原体的攻击。保护起作用的时间通常为在用活性化合物处理植物后1-10天,优选1-7天。
适宜依据本发明处理的植物和栽培植物包括所有具有遗传物质的植物,这些遗传物质赋予这些植物特别有利且有用的性质(无论是通过培育和/或生物技术手段获得的)。也适宜依据本发明处理的植物和栽培植物能抵抗一种或多种生物胁迫,即所述植物对动物和微生物害虫表现出更佳的防御性,例如抵抗线虫、昆虫、螨、植物病原真菌、细菌、病毒和/或类病毒。
本发明的通式(I)的化合物和杀菌组合物可用来治疗性或预防性地控制植物或作物的植物病原真菌。
因此,依据本发明的另一方面,本发明还提供了一种治疗性或预防性地控制植物或农作物植物病原真菌的方法,该方法的特征在于将本发明的通式(I)的化合物或杀菌组合物施用到种子、植物或植物的果实或者正在生长或需要生长植物的土壤中。
本发明的处理方法还可用于处理繁殖材料如块茎或根茎,并且可用于处理种子、幼苗或移植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如有关植物的干、茎或梗、叶子、花和果实。
依据本发明,所有植物和植物部分都进行处理。植物是指所有植物和植物群体,例如优良和不良野生植物、培育植物和植物品种(无论是否被植物品种或植物培育者权利保护)。培育植物和植物品种可以是通过常规繁殖和培育方法得到的植物,这些方法可得到一种或多种生物技术方法的辅助或补充。植物原生质体融合,随机和定向诱变,分子或遗传标记,或利用生物工程和遗传工程方法。植物部分是指植物的所有地上和地下部分以及器官,例如芽、叶、花和根,诸如树叶、针叶、茎、树枝、花、子实体、果实和种子以及根,球茎和根茎。作物和无性繁殖及有性繁殖材料,例如插条、球茎、根茎、纤匐枝和种子也属于植物部分。
可通过本发明方法控制的植物或作物疾病有:
白粉病(powdery mildew),例如小麦白粉病(Blumeria diseases),由小麦白粉菌(Blumeriagraminis)引起;叉丝单囊壳属病(Podosphaera diseases),由白叉丝单囊壳(Podosphaeraleucotricha)引起;单丝壳属病(Sphaerotheca diseases),由苍耳单丝壳(Sphaerothecafuliginea)引起;钩丝壳属病(Uncinula diseases),由葡萄钓丝壳(Uncinulanecator)引起;锈病;胶锈属病(Gymnosporangium diseases),由赛宾锈菌(gymnosporangiumsabinae)引起;驼孢锈病(Hemileia diseases),由咖啡驼孢锈菌(Hemileiavastatrix)引起;层锈菌属病(Phakopsora diseases),由豆薯层锈菌(Phakopsorapachyrhizi)或山马蝗层锈菌(Phakopsora meibomian)引起;柄锈菌属病(Puccinia diseases),由隐匿柄锈菌(Puccinia recondite)、禾柄锈菌(Pucciniagraminis)或条形柄锈菌(Puccinia striiformis)引起;单孢锈菌属病(Uromycesdiseases),由疣顶单胞锈菌(Uromycesndiculatus)引起;卵菌病(Oomycete diseases),例如白锈病(albugo diseases),由白锈菌(Albugo candida)引起;盘梗霉属病(Bremiadiseases),由莴苣盘梗霉(Bremia lactucae)引起;霜霉属病(Peronospora diseases),由豌豆霜霉(Peronospora pisi)引起;疫霉属病(Phytophthora diseases),由致病疫霉(Phytophthorainfestans)引起;单轴霉属病(Plasmopara diseases),由葡萄生单轴霉(Plasmopat)引起;腐霉属病(Pythiam diseases),由终极腐霉(Pythium ultimum)引起;假霜霉属(Pseudoperonospora diseases),由葎草假霜(Pseudoperonosporahumuli)或古巴假霜霉(Pseudoperonosporacubensis)引起;叶斑病(Leafspot disease)、污叶病(leafblotch disease)和叶枯病(leafblight disease),例如支链孢属病(Alternariadiseases),由茄链格孢(Alternaria solan)引起;尾孢霉属病(Cercospora diseases),由甜菜生尾孢(Cercosporabeticola)引起;金孢子菌属病(Cladiosporum diseases),由瓜枝孢(Cladosporiumcucumerinum)引起;旋孢腔菌病(Cochliobolus diseases),由禾旋孢腔菌(Cochliobolussativus)或宫部旋孢腔菌(Cochliobolusmiyabeanus)引起;刺盘孢属病(Colletotrichum diseases),由豆刺盘孢(Colletotrichumlindemuthanium)引起;油橄榄孔雀斑病(Cycloconium diseases),由油橄榄孔雀斑菌(Cycloconium)引起;腐皮壳菌层病(Diaporthe diseases),由桔柑间座壳(Diaporthecitri)引起;长孢属病(Gloeosporiumdiseases),由悦色盘长孢(Gloeosporiumlaeticolor)引起;小丛壳属病(Glomerelladiseases),由围小丛壳(Glomerellacingulata)引起;球座菌属病(Guignardiadiseases),由葡萄球座菌(Guignardiabidwell)引起;小球腔菌属病(Leptosphaeriadiseases),由十字花科小球腔菌(Leptosphaeria maculans)或颖枯小球腔菌(Letosphaerianodorum)引起;稻瘟病(Magnaporthe diseases),由稻瘟菌(Magnaporthegrisea)引起;球腔菌属病(Mycosphaerella diseases),由禾生球腔菌(Mycosphaerellagraminicola),落花生球腔菌(Mycosphaerellaarachidicola)或香蕉黑条叶斑病菌(Mycosphaerellafijiensis)引起;壳针孢属病(Phaeosphaeria diseases),由颖枯壳针孢(Phaeosphaerianodorum)引起;核腔菌属病(Pyrenophora diseases),由圆核腔菌(Pyrenophora teres)或偃麦草核腔菌(Pyrenophoratriticirepentis)引起;柱隔孢属病(Ramularia diseases),由辛加柱隔孢(RamulariacollocygnI)或白斑柱隔孢(Ramulariaareola)引起;喙孢属病(Rhynchosporium diseases),由黑麦喙孢(Rhynchosporiusecalis)引起;壳针孢属病(Septoria diseases),由芹菜小壳针孢(Septoria apii)或番茄壳针孢(eptorialycopercisi)引起;核瑚菌属病(yphuladiseases),由肉孢核瑚菌(Typhula incarnata)引起;黑星菌属病(Venturia diseases),由苹果黑星菌(Venturia inaequalis)引起;根、叶鞘和茎疾病,例如伏革菌病(Corticiumdiseases),由禾伏革菌(Corticiumgraminearum)引起;镰孢菌(霉)属病(Fusariumdiseases),由尖镰孢(Fusarium oxysporum)引起;鲟形属病(Gaeumannomyces diseases),由禾顶囊壳(GaeumannomycesgraminIs)引起;丝核菌属病(Rhizoctonia diseases),由立枯丝核菌(Rhizoctonia solani)引起;水稻叶鞘腐败病(Sarocladium diseases),由稻帚枝霉(Sarocladiumoryzae)引起;小核菌病(Sclerotium diseases),由稻腐小核菌(Sclerotium oryzae)引起;塔普斯(Tapesia)病,由塔普斯梭状芽胞杆菌(Tapesiaacuformid)引起;根串珠霉属病(Thielaviopsis diseases),由根串珠霉(Thielaviopsisbasicola)引起;耳穗和圆锥花序疾病,例如链格孢属病(Alternariadiseases),由链格孢(Alternaria spp.)引起;曲霉病(Aspergillus diseases),由黄曲霉(Aspergillus flavus)引起枝孢属病(Cladosporium diseases),由枝孢(Cladosporiumspp.)引起;麦角菌属病(Claviceps diseases),由麦角菌(Claviceps purpurea)引起;镰孢菌(霉)属病(Fusarium diseases),由大刀镰孢菌(Fusariumculmorum)引起;赤霉属病(Gibberelladiseases),由玉米赤霉(Gibberellazeae)引起;水稻云形病(Monographelladiseases),由水稻云形菌(Monographellaalis)引起;黑穗病和腥黑穗病,例如轴黑粉菌属病(Sphacelotheca diseases),由丝轴黑粉菌(Sphacelothecareiliana)引起;腥黑粉菌属病(Tilletia diseases),由小麦网腥黑粉菌(Tilletia caries)引起;条黑粉菌属病(Urocystis diseases),由隐条黑粉菌(Urocystis occulta引起;黑粉菌属病(Ustilagodiseases),由裸黑粉菌(Ustilago nuda)引起;果实腐烂和霉菌病,例如曲霉病(Aspergillus diseases),由黄曲霉(Aspergillus flavus)引起;葡萄孢属病(Botrytisdiseases),由灰葡萄孢(Botrytis cinerea)引起;青霉菌病(Penicillium di seases),由扩展青霉(Penicillium expansum)引起;根霉病(Rhizopus diseases),由匍枝根霉(Rhizopus stolonifer)引起;核盘菌属病(Sclerotinia diseases),由核盘菌(Sclerotiniasclerotiorum)引起;轮枝孢属病(Verticillium diseases),由黑白轮枝孢(Verticilliumalboatrum)引起;种子和土壤传播的腐烂,霉菌,枯萎,腐烂和猝倒病,例如链格孢属病(Alternaria diseases),例如由芥生链格孢(Alternariabrassicicola)引起;丝囊霉病(Aphanomyces diseases),由豌豆丝囊霉(Aphanomyceseuteiches)引起;壳二孢病(Ascochyta diseases),由壳二孢(Ascochyta lentis)引起;曲霉病(Aspergillusdiseases),由黄曲霉(Aspergillus flavus)引起;枝孢病(Cladosporium diseases),由多主枝孢(Cladosporium herbarum)引起;旋孢腔菌病(Cochliobolus diseases),由禾旋孢腔菌(Cochliobolus sativus)引起;刺盘孢属病(Colletotrichum diseases),由番茄刺盘孢(Colletotrichumcoccodes)引起;镰孢菌(霉)属病(Fusarium diseases),由大刀镰孢菌(Fusarium)引起;赤霉属病(Gibberella diseases),由玉蜀黍赤霉(Gibberellazeae)引起;球孢菌病(Macrophomina diseases),由豆类球孢菌(Macrophominaphaseolina)引起;雪霉病(Monographella diseases),由小麦雪霉(Monographella nivalis)引起;青霉菌病(Penicillium diseases),由扩展青霉Penicillium expansum)引起;茎点霉属病(Phomadiseases),由黑胫茎点霉(Phoma lingam)引起;拟茎点霉属病(Phomopsis diseases),由大豆拟茎点霉(Phomopsis sojae)引起;疫霉属病(Phytophthora diseases),由恶疫霉(Phytophthora cactorum)引起;核腔菌病(Pyrenophora diseases),由麦类核腔菌(Pyrenophoragraminea)引起;梨孢属病(Pyricularia diseases),由稻梨孢菌(Pyriculariaoryzae)引起;腐霉属病(Pythium diseases),由终极腐霉Pythium ultimum)引起;丝核菌属病(Rhizoctonia diseases),由立枯丝核菌(Rhizoctonia solan)引起;根霉病(Rhizopus diseases),由米根霉(Rhizopus oryzae)引起;小核菌病(Sclerotiumdiseases),由齐整小核菌(Sclerotium rolfsii)引起;壳针孢属病(Septoria diseases),由颖枯壳针孢(Septoria nodorum)引起;核瑚菌病(Typhula diseases),由肉孢核瑚菌(Typhula incarnata)引起;轮枝孢属病(Verticillium diseases),由大丽花轮枝孢(Verticilliumdahliae)引起;溃疡病(Canker)、松碎(broom)和梢枯病,例如丛赤壳属病(Nectria diseases),由干癌丛赤壳菌(Nectriagalligena)引起;枯娄病,例如链核盘菌病(Monilinia diseases),由核果链核盘菌(Monilinialaxa)引起;叶疱病或缩叶病,例如外担子菌病(xobasidium diseases),由坏损外担子菌(Exobasidiumvexans)引起;外囊菌属病(Taphrina diseases),由畸形外囊菌(Taphrina deformans)引起;木质植物的衰退病,例如依科病(Esca diseases),由根霉格孢菌(Phaemoniella clam dospora)引起;葡萄顶枯病(Eutypa dieback),由葡萄弯孢壳(Eutypalata)引起;灵芝病(Ganoderma diseases),由狭长孢灵芝(Ganoderma boninense)引起;硬孔菌病(Rigidoporus diseases),由木硬孔菌(Rigidoporuslinosus)引起;花和种子的疾病,例如葡萄孢属病(Botrytis diseases),由灰葡萄孢(Botrytis cinerea)引起;根茎类疾病,例如丝核菌属病(Rhizoctoniadiseases),例如由立枯丝核菌(Rhizoctonia solani引起;长蠕孢属病(Helminthosporiumdiseases),由茄病长蠕孢(Helminthosporium soi)引起;根肿病,例如根肿菌病(Plasmodiophora diseases),例如由芸苔根肿菌(Plasmodiophorabrassicae)引起;由细菌微生物引起的病,所述细菌微生物例如黄单胞菌,野油菜黄单胞菌水稻致病变种(Xanthomonas campestrispv.oryzae)假单胞菌,例如丁香假单胞菌黄瓜致病变种(Pseudomonas syringaepv.lachrymans);欧文氏菌,例如解淀粉欧文氏菌(Erwiniaamylovora)。
本发明化合物的制备方法
本发明还提供了制备式(I)化合物的方法,所述方法包括步骤:在惰性溶剂中,将化合物(VI)和化合物(VII)进行反应,从而得到式(I)化合物:
该方法的条件,例如反应物、溶剂、碱、所用化合物的量、反应温度、反应所需时间可参考本发明的实施例和描述根据需要选择。本发明化合物还可以任选将在本说明书中描述的或本领域已知的各种合成方法组合起来而方便的制得,这样的组合可由本发明所属领域的技术人员容易地进行。
本发明的主要优点包括:
1.本发明提供了一种结构新颖的具有高杀菌活性的化合物,所述化合物具有农业上的光谱杀菌活性,非常适合用于防治植物病原菌及相关疾病。
下面结合具体实施例,进一步阐述本发明。应理解,这些实施例仅用于说明本发明而不用于限制本发明的范围。下列实施例中未注明具体条件的实验方法,通常按照常规条件,或按照制造厂商所建议的条件。除非另外说明,否则百分比和份数按重量计算。
以下实施例以非限制性的方式说明了依据本发明的通式(I)的化合物的制备。
实施例1:制备N'-(4H-苯并吡喃-4-亚甲基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰腙(化合物1)
步骤1:制备3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸甲酯
在100ml的烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸(1.76g,10mmol)和甲醇(20ml)再加入浓H2SO4(1ml),加热回流4小时。反应完成后,用饱和NaHCO3溶液调节PH至8-9,乙酸乙酯萃取3次,合并有机相并旋干得到白色固体1.8g,直接用于下一步反应不做需要进一步纯化。
步骤2:制备3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼
在100ml烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸甲酯(1.8g,9.46mmol),水合肼(15ml)和乙醇(30ml),加热回流6小时。反应完成后,用乙酸乙酯萃取3次,合并有机相旋干得到白色固体1.71g,直接用于下一步反应不需要进一步纯化。
步骤3:制备3-(二甲氨基)-1-(2-羟基苯基)-2-烯-1-酮
在100ml的烧瓶中加入1-(2-羟基苯基)乙酮(1.36g,10mmol),N,N-二甲基甲酰胺二甲基缩醛(2.38g,20mmol)和甲苯(30ml),加热回流12小时。反应完成后,旋干有机相得到淡黄色固体1.85g,直接用于下一步反应不需要进一步纯化。
步骤4:制备4H-苯并吡喃-4-酮
在100ml烧瓶中加入3-(二甲氨基)-1-(2-羟基苯基)-2-烯-1-酮(1.85g,9.67mmol),浓HCl(8ml)和二氯甲烷(30ml),回流1h。反应完成后冷却至室温,除去水相,二氯甲烷萃取3次,饱和NaHCO3洗涤3次,无水硫酸钠干燥。旋干有机相得到白色固体1.29g,直接用于下一步反应不需要进一步纯化。
步骤5:制备N'-(4H-色烯-4-亚甲基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼
在100ml烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼(0.38g,2mmol),4H-苯并吡喃-4-酮(0.35g,2.4mmol)和无水乙醇(30ml)。再滴加3滴乙酸作催化剂,加热回流4小时,TLC跟踪。旋蒸去除多余溶剂,剩余固体中加入5ml水稀释,用乙酸乙酯萃取,合并有机相,再用饱和食盐水洗涤,所得油相干燥浓缩后得白色固体。粗品进一步过柱层析纯化,二氯甲烷/甲醇(v/v=20:1)洗脱,得到产物0.53g。
实施例2:3-(二氟甲基)-N'-(8-氟-4H-色烯-4-亚甲基)-1-甲基-1H-吡唑-4-甲酰腙(化合物2)
步骤1:制备3-(二甲氨基)-1-(2-羟基苯基)-2-烯-1-酮
在100ml的烧瓶中加入1-(2羟基苯基)乙酮(1.54g,10mmol),N,N-二甲基甲酰胺二甲基缩醛(2.38g,20mmol)和甲苯(30ml),加热回流12小时。反应完成后,旋干有机相得到白色固体1.85g,直接用于下一步反应不需要进一步纯化。
步骤2:制备4H-苯并吡喃-4-酮
在100ml烧瓶中加入3-(二甲氨基)-1-(2-羟基苯基)-2-烯-1-酮(1.97g,9.43mmol),浓HCl(8ml)和二氯甲烷(30ml),回流1h。反应完成后冷却至室温,除去水相,二氯甲烷萃取3次,饱和NaHCO3洗涤3次,无水硫酸钠干燥。旋干有机相得到黄色固体1.31g,直接用于下一步反应不需要进一步纯化。
步骤3:制备N'-(4H-色烯-4-亚甲基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰腙
在100ml烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼(0.38g,2mmol),4H-苯并吡喃-4-酮(0.39g,2.4mmol)和无水乙醇(30ml)。再滴加3滴乙酸作催化剂,加热回流4小时,TLC跟踪。旋蒸去除多余溶剂,剩余固体中加入5ml水稀释,用乙酸乙酯萃取,合并有机相,再用饱和食盐水洗涤,所得油相干燥浓缩后得白色固体。粗品进一步过柱层析纯化,二氯甲烷/甲醇(v/v=20:1)洗脱,得到产物0.57g。
实施例3:3-(二氟甲基)-N'-(8-氯-4H-色烯-4-亚甲基)-1-甲基-1H-吡唑-4-甲酰腙(化合物3)
制备过程参考实施例1,用1-(2-羟基-3-氯苯基)乙酮替换1-(2-羟基苯基)乙酮作为起始原料。
实施例4:3-(二氟甲基)-N'-(8-溴-4H-色烯-4-亚甲基)-1-甲基-1H-吡唑-4-甲酰腙(化合物4)
制备过程参考实施例1,用1-(2-羟基-3-溴苯基)乙酮替换1-(2-羟基苯基)乙酮作为起始原料。
实施例5:3-(二氟甲基)-1-甲基-N'-(喹啉-4(1H)-亚基)-1H-吡唑-4-甲酰腙(化合物34)
步骤1:3-(二甲基氨基)-1-(2-硝基苯基)丙-2-烯-1-酮
在100ml的烧瓶中加入2-硝基苯乙酮(1.65g,10mmol),N,N-二甲基甲酰胺二甲基缩醛(2.38g,20mmol)和甲苯(30ml),加热回流12小时。反应完成后,旋干有机相得到橙色固体1.85g,直接用于下一步反应不需要进一步纯化。
步骤2:喹啉-4(1H)-酮
在250ml的烧瓶中加入3-(二甲基氨基)-1-(2-硝基苯基)丙-2-烯-1-酮(1.85g,8.4mmol),钯碳(10%w/w,0.89g,0.84mmol),环己烯(40ml)和乙醇(60ml),在80℃下搅拌3小时。反应结束后,将悬浮液冷却至室温,抽滤,旋干滤液。加入乙酸乙酯(20ml)溶解,回流1小时,趁热抽滤,得到黄色固体(1.1g)。
步骤3:3-(二氟甲基)-1-甲基-N'-(喹啉-4(1H)-亚基)-1H-吡唑-4-甲酰腙
在100ml烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼(0.38g,2mmol),喹啉-4(1H)-酮(0.35g,2.4mmol)和无水乙醇(30ml)。再滴加3滴乙酸作催化剂,加热回流4小时,TLC跟踪。旋蒸去除多余溶剂,剩余固体中加入5ml水稀释,用乙酸乙酯萃取,合并有机相,再用饱和食盐水洗涤,所得油相干燥浓缩后得黄色固体。粗品进一步过柱层析纯化,二氯甲烷/甲醇(v/v=20:1)洗脱,得到产物0.69g。
实施例6:3-(二氟甲基)-N'-(8-氟喹啉-4(1H)-亚基)-1-甲基-1H-吡唑-4-甲酰腙(化合物35)
制备过程参考实施例5,用1-(3-氟-2-硝基苯基)乙酮替换2-硝基苯乙酮作为起始原料。
实施例7:N'-(苯并呋喃-3(2H)-亚基)-3-(二氟甲基)-1-甲基吡唑-4-甲酰腙(化合物55)
在100ml烧瓶中加入3-(二氟甲基)-1-甲基-1H-吡唑-4-碳酰肼(0.38g,2mmol),苯并呋喃-3(2H)-酮(0.32g,2.4mmol)和无水乙醇(30ml)。再滴加3滴乙酸作催化剂,加热回流4小时,TLC跟踪。旋蒸去除多余溶剂,剩余固体中加入5ml水稀释,用乙酸乙酯萃取,合并有机相,再用饱和食盐水洗涤,所得油相干燥浓缩后得白色固体。粗品进一步过柱层析纯化,二氯甲烷/甲醇(v/v=20:1)洗脱,得到产物0.48g。1H NMR(500MHz,Chloroform-d)δ8.07(s,1H),7.68(dd,J=7.4,2.0Hz,1H),7.46(td,J=7.5,2.0Hz,1H),7.29(td,J=7.5,2.0Hz,1H),7.22(s,1H),6.88(dd,J=7.5,2.0Hz,1H),4.78(s,2H),3.83(s,3H).
实施例8:3-(二氟甲基)-N'-(7-氟苯并呋喃-3(2H)-亚基)-1-甲基-1H-吡唑-4-甲酰腙(化合物56)
制备过程参考实施例7,用7-氟苯并呋喃-3(2H)-酮替换苯并呋喃-3(2H)-酮作为起始原料。
实施例9:N'-(4H-色烯-4-亚基)-3-(三氟甲基)吡嗪-2-甲酰腙(化合物80)
制备过程参考实施例1,用3-(三氟甲基)吡嗪-2-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例10:2-氯-N'-(4H-色烯-4-亚基)烟酸酰腙(化合物86)
制备过程参考实施例1,用2-氯烟酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例11:N'-(4H-色烯-4-亚基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰腙(化合物92)
制备过程参考实施例1,用1-甲基-3-(三氟甲基)-1H-吡唑-4-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例12:N'-(4H-色烯-4-亚基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰腙(化合物98)
制备过程参考实施例1,用3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例13:N'-(4H-色烯-4-亚基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰腙(化合物104)
制备过程参考实施例1,用5-氟-1,3-二甲基-1H-吡唑-4-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例14:5-氯-N'-(4H-色烯-4-亚基)-1,3-二甲基-1H-吡唑-4-甲酰腙(化合物110)
制备过程参考实施例1,用5-氯-1,3-二甲基-1H-吡唑-4-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例15:N'-(4H-色烯-4-亚基)-2-甲基-4-(三氟甲基)噻唑-5-甲酰腙(化合物116)
制备过程参考实施例1,用2-甲基-4-(三氟甲基)噻唑-5-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例16:N'-(4H-色烯-4-亚基)-2-(三氟甲基)苯甲酰腙(化合物122)
制备过程参考实施例1,用2-(三氟甲基)苯甲酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例17:N'-(4H-色烯-4-亚基)-2-甲基-5,6-二氢-1,4-氧硫-3-甲酰腙(化合物128)
制备过程参考实施例1,用2-甲基-5,6-二氢-1,4-氧硫烷-3-羧酸替换3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸作为起始原料。
实施例18:本发明化合物的杀菌离体活性测试:
实验A:对水稻纹枯病离体预防活性测试
将测试的化合物溶解在DMSO中以制备20mg/mL的溶液,然后再与PDA混合。将含有浓度为20mg/L化合物的培养基倒入无菌培养皿中进行初步筛选。在28℃下72h后,测量每个菌株的菌落直径。抑制百分率的计算为(C-A)/(C-B)×100%,其中A代表含有受试化合物的培养皿中的菌落直径,B代表菌丝盘直径,C代表对照培养皿中的平均菌落直径。每个处理重复三次。表A表示合成化合物的活性数据。
实验B:对灰霉病离体预防活性测试
将测试的化合物溶解在DMSO中以制备20mg/mL的溶液,然后再与PDA混合。将含有浓度为20mg/L化合物的培养基倒入无菌培养皿中进行初步筛选。在28℃下72h后,测量每个菌株的菌落直径。抑制百分率的计算为(C-A)/(C-B)×100%,其中A代表含有受试化合物的培养皿中的菌落直径,B代表菌丝盘直径,C代表对照培养皿中的平均菌落直径。每个处理重复三次。表B表示合成化合物的活性数据。
实验C:对油菜菌核病离体预防活性测试
将测试的化合物溶解在DMSO中以制备20mg/mL的溶液,然后再与PDA混合。将含有浓度为20mg/L化合物的培养基倒入无菌培养皿中进行初步筛选。在28℃下48h后,测量每个菌株的菌落直径。抑制百分率的计算为(C-A)/(C-B)×100%,其中A代表含有受试化合物的培养皿中的菌落直径,B代表菌丝盘直径,C代表对照培养皿中的平均菌落直径。每个处理重复三次。表C表示合成化合物的活性数据。
实验D:对油赤霉病离体预防活性测试
将测试的化合物溶解在DMSO中以制备20mg/mL的溶液,然后再与PDA混合。将含有浓度为20mg/L化合物的培养基倒入无菌培养皿中进行初步筛选。在28℃下144h后,测量每个菌株的菌落直径。抑制百分率的计算为(C-A)/(C-B)×100%,其中A代表含有受试化合物的培养皿中的菌落直径,B代表菌丝盘直径,C代表对照培养皿中的平均菌落直径。每个处理重复三次。表C表示合成化合物的活性数据。
提供化合物的NMR数据见表1,具体结构如表所示。
表1
表2显示本发明通式(I)化合物的非限制性例子和离体活性数据;
表2
由本发明的前述离体结果可以看出,本发明提供的化合物具有优异的杀菌活性,且对水稻纹枯病和灰霉病、油菜菌核病、赤霉病的防效均不低于现有技术提供的商品化药剂氟唑菌酰胺。
本发明的典型化合物的杀菌活体活性测试:
实验A:小麦赤霉病测试(叶片法)
剪取相应数量的一叶一心期小麦叶片00,保持叶片高度在7cm左右,放置于写好标签的10mL离心管中(每离心管中24片叶),将离心管口用单层纱布封口。将叶片浸入装有药液的离心管中后开始计时,30s后用镊子夹出叶片,放置于写好标签的双层纸巾上,晾干;浸药后1小时左右,将晾干药液的叶片分装至写好标签的1%水琼脂试管中,每试管中8片叶。将试管放置于试管架上,于人工气候箱中培养。设定程序如下:温度25℃,12小时光照/12小时黑暗,先黑暗后光照。药剂处理后6天进行调查。以1%水琼脂面为起始点,用卡尺测量菌丝生长高度。按以下公式计算各处理浓度对小麦赤霉病的菌丝生长抑制率,单位为百分率(%),计算结果保留小数点后两位。
菌丝生长抑制率(%)=(空白对照菌丝生长高度–药剂处理菌丝生长高度)/空白照菌丝生长高度×100%
表3显示本发明通式(I)化合物的非限制性例子和活体活性数据;
表3
由上表3可以看出,与已知的杀菌剂啶酰菌胺相比,本发明的化合物在活体上也表现出优异的杀菌效果,由此也说明本发明提供的苯并杂环酰腙类化合物对于开发新的农用杀菌剂具有重要的指导意义。
在本发明提及的所有文献都在本申请中引用作为参考,就如同每一篇文献被单独引用作为参考那样。此外应理解,在阅读了本发明的上述讲授内容之后,本领域技术人员可以对本发明作各种改动或修改,这些等价形式同样落于本申请所附权利要求书所限定的范围。
Claims (10)
1.一种式(I)化合物,其光学异构体、顺反异构体或其农药学上可接受的盐:
式中:
A选自下组:取代或未取代的苯环或萘环;取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-10元杂环或杂芳环;
G为取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-10元杂环或杂芳环;
其中,取代指所述基团独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基X取代:
X表示氢(H)、卤素(如F、Cl、Br或I)、羟基、巯基、硝基、羧基、酯基、氰基、独立地任选一个或多个取代基取代的C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷硫基、C1-C8卤代烷硫基、C1-C8烷胺基、C1-C8二烷基胺基、C1-C8卤代烷胺基、C1-C8卤代二烷基胺基、C3-C8环烷基、C2-C8烯基、C2-C8卤代烯基、C2-C8烯氧基、C2-C8炔基、C5-C7环烯基、C1-C8烷基亚硫酰基、C1-C8亚硫酰基烷基、C1-C8烷基磺酰基、C1-C8磺酰基烷基、C1-C8烷基羰基、C1-C8羰基烷基、C1-C6烷氧基羰基、C1-C8羰基烷氧基、C1-C8烷胺基羰基、C1-C8羰基烷胺基、C1-C8烷胺基硫代羰基、C1-C8硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、、C1-C6三烷基甲硅烷基、C1-C6硼酯基、5-7元非芳杂环基;
或者X独立地为取代或未取代地:苯基、苄基、苯甲酰基、偶氮芳基、苯氧基5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环系统;
其中,所述取代指X独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基取代:氢、卤素、羟基、巯基、氰基、硝基、氧代(=O)、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷胺基、C1-C6二烷基胺基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯氧基、C2-C6炔基、C5-C7环烯基、C1-C6烷基亚硫酰基、C1-C6亚硫酰基烷基、C1-C6烷基磺酰基、C1-C6磺酰基烷基、C1-C6烷基羰基、C1-C6羰基烷基、C1-C6烷氧基羰基、C1-C6羰基烷氧基、C1-C6烷胺基羰基、C1-C6羰基烷胺基、C1-C6烷胺基硫代羰基、C1-C6硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C1-C6三烷基甲硅烷基、C1-C6硼酯基、苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环;
Q表示苯环上0-4个(优选地为1、2、3或4个)取代基,且各Q独立任选地选自下组:氢(H)、卤素(包括F、Cl、Br或I,下同)、羟基、巯基、硝基、羧基、酯基、氰基或独立地任选一个或多个取代基取代的C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷硫基、C1-C8卤代烷硫基、C1-C8烷胺基、C1-C8二烷基胺基、C1-C8卤代烷胺基、C1-C8卤代二烷基胺基、C3-C8环烷基、C2-C8烯基、C2-C8卤代烯基、C2-C8烯氧基、C2-C8炔基、C5-C7环烯基、C1-C8烷基亚硫酰基、C1-C8亚硫酰基烷基、C1-C8烷基磺酰基、C1-C8磺酰基烷基、C1-C8烷基羰基、C1-C8羰基烷基、C1-C8烷氧基羰基、C1-C8羰基烷氧基、C1-C8烷胺基羰基、C1-C8羰基烷胺基、C1-C8烷胺基硫代羰基、C1-C8硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C1-C6三烷基甲硅烷基、C1-C6硼酯基、5-7元非芳杂环基;
或者各Q独立地为取代或未取代地:苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环系统;且
其中所述取代指Q独立任选的被一个或多个(如1、2、3或4个)选自下组的取代基取代:氢、卤素、羟基、巯基、氰基、硝基、氧代(=O)、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷胺基、C1-C6二烷基胺基、C3-C6环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6烯氧基、C2-C6炔基、C5-C7环烯基、C1-C6烷基亚硫酰基、C1-C6亚硫酰基烷基、C1-C6烷基磺酰基、C1-C6磺酰基烷基、C1-C6烷基羰基、C1-C6羰基烷基、C1-C6烷氧基羰基、C1-C6羰基烷氧基、C1-C6烷胺基羰基、C1-C6羰基烷胺基、C1-C6烷胺基硫代羰基、C1-C6硫代羰基烷胺基、C3-C6环烷氧基;C3-C6环烷氨基、C3-C6三烷基甲硅烷基、C2-C6硼酯基、苯基、苄基、苯甲酰基、偶氮芳基、苯氧基、5-或6-元杂芳环或芳族8-、9-或10-元稠合杂双环。
2.如权利要求1所述的化合物,其特征在于,A选自下组:取代或未取代的苯环、或取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5元或6元杂环或杂芳环,优选地,A选自下组:
3.如权利要求1所述的化合物,其特征在于,G为取代或未取代的具有1-4个(优选地2或3个)选自N、O、S的杂原子的5-6元杂环或杂芳环;优选地,G选自下组:
4.如权利要求2-4任一所述的化合物,其特征在于,G是取代或未取代的:吡喃、吡啶或呋喃,如下图所示,其中取代基X如权利要求1中X定义
5.如权利要求1所述的化合物,其特征在于,式I化合物结构如式V;
最优选的Q为单卤素取代或者双卤素基团。
6.如权利要求1所述的化合物,其特征在于,所述化合物表2所示的化合物1-133。
7.一种农药组合物,包括如权利要求1-6任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐;和农药学上可接受的载体。
8.一种如权利要求1所述的化合物的制备方法,其特征在于,所述方法包括步骤:在惰性溶剂中,将化合物(VI)和化合物(VII)进行反应,从而得到式(I)化合物
9.一种如权利要求1-6任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐,或如权利要求7所述的农药组合物的用途,其特征在于,用于防治植物病原菌及相关疾病或制备杀菌剂组合物。
10.一种防治作物的植物病原菌及相关疾病的方法,其特征在于,将如权利要求1-6任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐或如权利要求7所述的农药组合物施用到植物在其中生长或能够在其中生长的土壤中,或施用到植物的植株上,如根、茎、叶子、果实和/或种子上,从而防治所述植物病原菌及相关疾病。
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