CN113024379A - 一种含羰基化合物及其制备方法和用途 - Google Patents
一种含羰基化合物及其制备方法和用途 Download PDFInfo
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- CN113024379A CN113024379A CN202110272320.2A CN202110272320A CN113024379A CN 113024379 A CN113024379 A CN 113024379A CN 202110272320 A CN202110272320 A CN 202110272320A CN 113024379 A CN113024379 A CN 113024379A
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- alkylene
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- YPJUNDFVDDCYIH-UHFFFAOYSA-N perfluorobutyric acid Chemical compound OC(=O)C(F)(F)C(F)(F)C(F)(F)F YPJUNDFVDDCYIH-UHFFFAOYSA-N 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
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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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
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- A—HUMAN NECESSITIES
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- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
- C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
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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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明公开了一种含羰基化合物及其制备方法和用途,化合物结构如通式I所述,各取代基的定义如说明书和权利要求书所述。本发明的化合物对多种植物真菌病害具有广谱的杀菌活性,可单独或与其他药剂复配用于多种植物真菌病害的防治,特别对黄瓜霜霉病、黄瓜炭疽病、小麦白粉病、玉米锈病、水稻纹枯病、黄瓜灰霉病具有优异的防治效果。
Description
技术领域
本发明涉及含羰基化合物及其制备方法和用途。
背景技术
植物病原菌对植物的生长有很大的危害,每年给农业造成巨大的损失,为防止植物病害的发生,减少由其造成的损失,大量的抑菌及杀菌活性化合物被报道并应用。由于抗药性等方面的因素,新杀菌剂的研发一直是各农药企业和科研人员关注的热点。
酰胺类化合物作为杀菌剂已有几十年的历史,至今已有30多个品种商品化,该类杀菌剂中的大多数品种对卵菌纲病害有较好的防治效果。由于长期的使用,目前该类化合物已经开始产生抗药性,需要开发高效,低毒,无交互抗性的杀菌剂。
发明内容
本发明的目的是提供含羰基化合物用于防治植物病菌。
本发明的第一方面,提供具有通式(I)所示结构的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐,
式中,T为H、氰基或者取代或未取代的选自下组的基团:C1-C8烷基、C2-C6烯基、C3-C6环烷基、C2-C6烯氧基、C2-C6炔基、C2-C6炔氧基、C1-C6烷氧基、C3-C6环烷氧基、C5-C7环烯基、4-8元杂环基、C6-C10芳基、-OC(=O)(C6-C10芳基)、-OC(=O)(C6-C10芳基)(C2-C6烯基)、-OC(=O)(C1-C8亚烷基)(C6-C10芳基)、-OC(=O)(C1-C8亚烷基)苯基(C2-C6烯基)、4-8元杂芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C8烷基、C3-C6环烷基、C1-C8卤代烷基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)C1-C8烷基、-C(=O)C3-C6环烷基、-C(=O)C1-C8卤代烷基、-C(=O)C6-C10芳基、-C(=O)4-8元杂芳基、-C(=O)4-8元杂环基;其中所述取代是指被选自下组的一个或多个基团取代:氰基、羟基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C8烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)O(C1-C8烷基)或C1-C6硫代烷基。
在另一优选例中,T为H、或者为取代或未取代的选自下组的基团:C1-C6烷基、C2-C6烯基、C3-C6环烷基、5-7元杂环基、苯基、5-7元杂芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C8烷基、C3-C6环烷基、C1-C8卤代烷基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)C1-C8烷基、-C(=O)C3-C6环烷基、-C(=O)C1-C8卤代烷基、-C(=O)C6-C10芳基、-C(=O)4-8元杂芳基、-C(=O)4-8元杂环基;其中所述取代是指被选自下组的一个或多个基团取代:氰基、羟基、氧代(=O)、C1-C8烷基、氟、氯、溴、C1-C6卤代烷基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、C2-C6炔基、苯基、4-8元杂芳基、5-7元杂环基、-C(=O)O(C1-C8烷基)或C1-C6硫代烷基。
在另一优选例中,T为H、或者为取代或未取代的选自下组的基团:C1-C4烷基、苯基、C2-C6烯基、C3-C6环烷基、5-6元杂环基;其中所述取代是指被选自下组的一个或多个基团取代:氟、氯、溴、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、5-6元杂环基、苯基。
在另一优选例中,T为表1中列出的任一基团。
Z为O或NR2;其中,R2为氢、或者取代或未取代的选自下组的基团:C1-C8烷基、C2-C6烯基、C3-C6环烷基、C2-C6烯氧基、C2-C6炔基、C2-C6炔氧基、C1-C6烷氧基、C3-C6环烷氧基、C5-C7环烯基、4-8元杂环基、C6-C10芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基);其中所述取代是指被选自下组的一个或多个基团取代:卤素(氟、氯、溴)、氰基、C1-C8烷基、C1-C8卤代烷基、硝基、羟基、C2-C6烯基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基或C1-C6硫代烷基。
在另一优选例中,Z为O或NR2;其中,R2为氢、或者为取代或未取代的选自下组的基团:-(C1-C4亚烷基)(5-7元杂芳基)、-(C1-C4亚烷基)(C6-C10芳基)、-(C1-C4亚烷基)(C3-C6环烷基)、-(C1-C4亚烷基)(4-10元杂环基)、-(C1-C4亚烷基)NHC(=O)(4-10元杂芳基);其中所述取代是指被选自下组的一个或多个基团取代:卤素(氟、氯、溴)、氰基、C1-C4烷基、C1-C4卤代烷基、硝基、羟基、C2-C4烯基、C2-C4炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4硫代烷基。
在另一优选例中,Z为O或NH。
R1为取代或未取代的选自下组的基团:C1-C10烷基、C2-C6烯基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C10环烷基、-(C1-C8亚烷基)(C3-C10环烷基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(4-8元杂环基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、卤代4-8元杂芳基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C8烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-O(C6-C10芳基)或C1-C6硫代烷基。
在另一优选例中,R1为取代或未取代的选自下组的基团:C1-C6烷基、C2-C4烯基、C2-C4炔基、苯基、5-7元杂芳基、5-7元杂环基、C3-C8环烷基、-(C1-C6亚烷基)(C3-C8环烷基)、-(C1-C6亚烷基)苯基、-(C1-C6亚烷基)(4-10元杂芳基)、-(C1-C6亚烷基)(5-7元杂环基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C6烷基、氟、氯、溴、C1-C4卤代烷基、卤代5-7元杂芳基、-C(=O)NH(C1-C6烷基)、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、苯基、4-8元杂芳基、4-8元杂环基、-O-苯基或C1-C6硫代烷基。
在另一优选例中,R1为C3-C8环烷基、-(C1-C8亚烷基)(C3-C8环烷基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(4-8元杂环基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、卤代4-8元杂芳基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、苯基、4-8元杂芳基、4-8元杂环基、-O-苯基)或C1-C6硫代烷基。
在另一优选例中,R1为-(C1-C8亚烷基)(C6-C10芳基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、卤代4-8元杂芳基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C8烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-O(C6-C10芳基)或C1-C6硫代烷基。
在另一优选例中,R1为C2-C4烯基、苯基、C3-C8环烷基、-(C1-C4亚烷基)(C3-C8环烷基)、-(C1-C4亚烷基)苯基、-(C1-C4亚烷基)(4-10元杂芳基)、-(C1-C4亚烷基)(5-7元杂环基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C4烷基、氟、氯、溴、C1-C4卤代烷基、卤代5-7元杂芳基、-C(=O)NH(C1-C4烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烯基、硝基、羟基、C2-C6炔基、苯基、5-7元杂芳基、5-7元杂环基、-O-苯基或C1-C6硫代烷基。
在另一优选例中,R1为表1中列出的任一基团。
在另一优选例中,所述化合物具有以下结构:R1-OCO(C1-C6烷基),较佳为R1-OCO(C1-C4烷基),其中上述烷基任选被选自下组的1、2、3、4、5、6、7、8、9或10个基团取代:氰基、羟基、氧代(=O)、C1-C4烷基、氟、氯、溴、C1-C4卤代烷基(较佳为三氟甲基)、-C(=O)NH(C1-C4烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基(较佳为三氟甲氧基)、C2-C4烯基、硝基、C2-C4炔基、苯基、5-7元杂芳基、5-7元杂环基。
在另一优选例中,所述化合物具有以下结构:R1-OCOPh,其中上述Ph任选被选自下组的1、2、3、4或5个基团取代:氰基、羟基、氧代(=O)、C1-C4烷基、氟、氯、溴、C1-C4卤代烷基(较佳为三氟甲基)、-C(=O)NH(C1-C4烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基(较佳为三氟甲氧基)、C2-C4烯基、硝基、C2-C4炔基、苯基、5-7元杂芳基、5-7元杂环基。
在另一优选例中,所述化合物具有以下结构:Ph-(C1-C4亚烷基)OCO(C1-C6烷基),较佳为Ph-(C1-C4亚烷基)OCO(C1-C4烷基),其中上述烷基任选被选自下组的1、2、3、4、5、6、7、8、9或10个基团取代:氰基、羟基、氧代(=O)、C1-C4烷基、氟、氯、溴、C1-C4卤代烷基(较佳为三氟甲基)、-C(=O)NH(C1-C4烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基(较佳为三氟甲氧基)、C2-C4烯基、硝基、C2-C4炔基、苯基、-O-苯基、5-7元杂芳基、5-7元杂环基。
在另一优选例中,所述化合物为表1中的任一化合物。
本发明的第二方面,提供了一种农用组合物,包含:
(a)0.001-99.99wt%的本发明第一方面所述的化合物、其光学异构体、顺反异构体、或其药学上可接受的盐、或者它们的组合;以及
(b)农药学上可接受的载体和/或赋形剂。
在另一优选例中,组分(a)占所述药物组合物总重量的0.001-99.99wt%;较佳地为0.01-99.9wt%;更佳地为0.05-90wt%。
在本发明中提供了一种以含羰基化合物为活性成分的药物。在需要的时候,在所述药物中还可以加入一种或多种农药制剂中可接受的载体,所述载体包括农药制剂中常规的稀释剂、赋形剂、填充剂、粘合剂、润湿剂、吸收促进剂、表面活性剂、润滑剂、稳定剂、消泡剂、硅藻土等。制成的药物的剂型也是多样的,可以是粉剂、乳剂、水剂、颗粒剂、缓蚀剂、泡腾片剂等。
本发明的另一方面,提供第一方面所述化合物,其光学异构体、顺反异构体或其农药学上可接受的盐或者如第二方面所述的农药组合物的用途,用于制备杀菌剂。
在另一优选例中,所述杀菌剂防治以下病害:黄瓜霜霉病、黄瓜灰霉病、玉米锈病、水稻纹枯病、小麦白粉病。
本发明的另一方面,提供一种防治植物病菌的方法,包括给植物施用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者如第二方面所述的农药组合物。
本发明合成含羰基化合物,制备方法简便易行,操作简单,产物纯化容易,成本较低,稳定性提高。
本发明含羰基化合物,经试验证实有明显的抗菌活性,用于防治农作物、果树、中草药及花卉病害。
本发明的实质性的特点可从下述的实施例得以体现,但它不应视为是对本发明作任何限制。
具体实施方式
本申请的发明人经过广泛而深入的研究,研发出一系列含羰基化合物,其具有多重抗菌活性,不仅对黄瓜霜霉病、黄瓜炭疽病具有明显的抑制作用,而且对小麦白粉病、玉米锈病、水稻纹枯病、黄瓜灰霉病也有较好的抑制活性,可以作为农药用于农业生产中。
基团定义
术语“C1-C8烷基”是指具有1-8个碳原子的直链或支链烷基,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基或类似基团。
术语“C2-C6烯基”指具有2-6个碳原子的直链或支链的烯基,例如乙烯基、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-C6炔基”是指具有2-6个碳原子的直链或支链的炔基,例如乙炔基、丙炔基或类似基团。
术语“C3-C6环烷基”指具有3-7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“C5-C7环烯基”指具有5-7个碳原子的、具有一个或多个双键的环状烯基,例如环戊烯基、环己烯基、环庚烯基、1,3-环己二烯基、1,4-环己二烯基或类似基团。
术语“C1-C6烷氧基”指具有1-6个碳原子的直链或支链烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基或类似基团。
术语“卤素”指氟、氯、溴或碘。术语“卤代的”指被相同或不同的一个或多个上述卤原子取代的基团,例如三氟甲基、五氟乙基、七氟异丙基或类似基团。
术语“烷基”是指烷烃分子中少掉一个氢原子而成的基团。
术语“环”或“环系”指碳环或杂环。
术语“杂环基”、“杂芳基”指形成所述杂环或杂芳环骨架的原子中至少一个原子不是碳,为氮、氧或硫。通常,“杂环基”、“杂芳基”包含不超过4(如1、2或3)个氮、不超过2(如1或2)个氧和/或不超过2(如1或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。例如优选的杂环基为含1、2、3或4个选自氮、氧或硫的杂原子的环,例如,所述杂环基为吗啉基、哌啶基、哌嗪基、四氢吡咯基、四氢呋喃基、四氢吡喃基等。例如优选的杂芳基为含1、2、3或4个选自氮、氧或硫的杂原子的环,例如,所述杂芳基基为吡啶基、噻唑基、异噻唑基、噻吩基、呋喃基、吡咯基、吡唑基、嘧啶基、苯并吡咯基、苯并呋喃基、苯并噻吩基、吲哚基、苯并咪唑基、喹啉基、哒嗪基等。
术语“DCC”指二环己基碳二亚胺。术语“DMAP”指4-二甲氨基吡啶。
术语“THF”指四氢呋喃。
本发明活性物质的杀菌活性
术语“本发明的活性物质”或“本发明的活性化合物”是指通式(I)所示结构的化合物或农药学上可接受的盐。其含N、O的杂环结构,具有显著的杀菌活性,且杀菌谱广、稳定性强。
术语“农药学上可接受的盐”指该盐的阴离子在形成杀菌剂药学上可接受的盐时为已了解的和可接受的。较佳地,该盐为水溶性的。合适的,由式(I)的化合物形成的酸加成盐包括无机酸形成的盐,例如盐酸盐、磷酸盐、硫酸盐、硝酸盐;及包括有机酸形成的盐,如羧酸盐。
本发明所涉及的化合物尤其对黄瓜霜霉病、黄瓜炭疽病、小麦白粉病、玉米锈病、水稻纹枯病、黄瓜灰霉病有较好的防治效果。
含本发明活性物质的杀菌剂组合物
可将本发明的活性物质以常规的方法制备成杀菌剂组合物。这些活性化合物可做成常规的制剂,例如溶液剂、乳剂、混悬剂、粉剂、泡沫剂、糊剂、颗粒剂、气雾剂、用活性物质浸渍的天然的和合成的材料、在多聚物中的微胶囊、用于种子的包衣复方、和与燃烧装置一块使用的制剂,例如烟熏药筒、烟熏罐和烟熏盘,以及ULV冷雾(Cold mist)和热雾(Warmmist)制剂。
这些制剂可用已知的方法生产,例如,将活性化合物与扩充剂混合,这些扩充剂就是液体的或液化气的或固体的稀释剂或载体,并可任意选用表面活性剂即乳化剂和/或分散剂和/或泡沫形成剂。例如在用水作扩充剂时,有机溶剂也可用作助剂。
用液体溶剂作稀释剂或载体时,基本上是合适的,如:芳香烃类,例如二甲苯、甲苯或烷基萘;氯化的芳香或氯化的脂肪烃类,例如氯苯、氯乙烯或二氯甲烷;脂肪烃类,例如环己烷或石蜡,例如矿物油馏分;醇类,例如乙醇或乙二醇以及它们的醚和脂类;酮类,例如丙酮、甲乙酮、甲基异丁基酮或环已酮;或不常用的极性溶剂,例如二甲基甲酰胺、二甲基亚砜以及水。
液化气的稀释剂或载体,指的是在常温常压下将成为气体的液体,例如气溶胶推进剂,如卤化的烃类以及丁烷、丙烷、氮气和二氧化碳。
固体载体可用磨碎的天然的矿物质,例如高岭土、粘土、滑石、石英、活性白土、蒙脱土、或硅藻土;和磨碎的合成的矿物质,例如高度分散的硅酸、氧化铝和硅酸盐。供颗粒用的固体载体是碾碎的和分级的天然锆石,例如方解石、大理石、浮石、海泡石、白云石、无机和有机粗粉合成的颗粒,以及有机材料例如锯木屑、椰子壳、玉米棒子和烟草梗的颗粒等。
非离子的和阴离子的乳化列可用作乳化剂和/或泡沫形成剂。例如聚氧乙烯-脂肪酸酯类,聚氧乙烯-脂肪醇醚类,烷芳基聚乙二醇醚类,烷基磺酸酯类,烷基硫酸酯类,芳基磺酸酯类以及白蛋白水解产物。分散剂包括木质素亚硫酸盐废液和甲基纤维素。
在制剂中可以用粘合剂,例如羧甲基纤维素和以粉末、颗粒或乳液形式的天然和合成的多聚物,例如阿拉伯胶、聚乙烯基醇和聚乙烯醋酸酯。
可以用着色剂例如无机染料,如氧化铁、氧化钴和普鲁士蓝;有机染料,如偶氮染料或金属酞菁染料;痕量营养剂,如铁、锰、硼、铜、钴、铝和锌的盐等。
本发明的这些活性化合物可与其他活性化合物制成一种混合物存在于它们的商品制剂中或从这些制剂制备的使用剂型中,这些其他的活性化合物为杀虫剂、杀菌剂、杀真菌剂、除草剂、生长控制剂等。杀虫剂包括,例如磷酸酯类、氨基甲酸酯类、氯化烃类以及由微生物产生的物质,如阿维菌素等,杀真菌剂包括甲氧基丙烯酸酯类、酰胺类、三唑类等。
此外,本发明的这些活性化合物也可与增效剂制成一种混合物存在于它们的商品制剂中或从这些制剂制备的使用剂型中,这些增效剂是提高活性化合物作用的化合物,由于活性化合物本身有活性,也可不必加增效剂。
这些制剂通常含有所述杀菌剂组合物总重量的0.001-99.99重量%,优选0.01-99.9重量%,更优选0.05-90重量%的本发明的活性化合物。商品制剂或使用剂型中的活性化合物的浓度可在广阔的范围内变动。使用剂型中的活性化合物的浓度可从0.0000001-100%(g/v),最好在0.0001与1%(g/v)之间。
本发明化合物的制备方法
本发明通式(I)所示化合物可通过如下的方法制得,然而该方法的条件,例如反应物、溶剂、碱、所用化合物的量、反应温度、反应所需时间等不限于下面的解释。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的进行。
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。所述材料如无特别说明均能从公开商业途径而得。除非另外说明,否则百分比和份数按重量计算。
实施例1:2-溴乙酸-3,5-二氯苄酯的制备
将1mmol 3,5-二氯苄醇溶解在5ml四氢呋喃中,之后加入1mmol的DCC和催化量的DMAP,然后加入1mmol溴乙酸。常温过夜搅拌,TLC追踪反应。反应结束后,加入5ml的水,5ml的乙酸乙酯,水相用乙酸乙酯萃取。合并有机相,使用饱和氯化钠洗,用无水硫酸镁干燥,蒸除溶剂。粗产物使用柱层析纯化,得到3,5-二氯苄基-2-溴-乙酸乙酯(收率73%,无色液体)。1H NMR(400MHz,CDCl3 d)δ:7.33(t,J=1.6Hz,1H),7.25(d,J=1.6Hz,2H),5.15(s,2H),4.13(s,2H);HRMS(ESI)m/z[M+H]+C9H8BrCl2O2,计算值:296.9079,实测值:296.9069.
实施例2:2-氯乙酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用氯乙酸代替溴乙酸。(收率66%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.27(t,J=2.0Hz,1H),7.19(d,J=1.9Hz,2H),4.92(s,2H),4.50(s,2H).;HRMS(ESI)m/z[M+H]+C9H8Cl3O2,计算值:252.9584,实测值:252.9583.
实施例3:3,3,3-三氟丙酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3,3,3-三氟丙酸代替溴乙酸。(收率67%,无色液体)。1H NMR(400MHz,CDCl3 d)δ:7.34(t,J=1.8Hz,1H),7.24(d,J=1.8Hz,2H),5.14(s,2H),3.26(q,J=10.0Hz,2H);HRMS(ESI)m/z[M+H]+C10H8Cl2O2F3,计算值:286.9848,实测值:286.9843.
实施例4:2,2,3,3,3-五氟丙酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用2,2,3,3,3-五氟丙酸代替溴乙酸。(收率61%,无色液体)。1H NMR(400MHz,CDCl3 d)δ:7.39(t,J=1.8Hz,1H),7.26(d,J=1.8Hz,2H),5.31(s,2H);HRMS(ESI)m/z[M+H]+C10H5Cl2O2F5,计算值:321.9587,实测值:321.9587.
实施例5:2,2,3,3,4,4,4-七氟丁酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用2,2,3,3,4,4,4-七氟丁酸代替溴乙酸。(收率62%,无色液体)。1H NMR(400MHz,CDCl3 d)δ:7.35(t,J=2.6Hz,1H),7.28(d,J=1.8Hz,2H),4.44(s,2H);HRMS(ESI)m/z[M+H]+C11H6Cl2O2F7,计算值:372.9628,实测值:372.9628.
实施例6:2,2,2-三氯乙酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用2,2,2-三氯乙酸代替溴乙酸。(收率65%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.37(t,J=1.8Hz,1H),7.30(d,J=1.8Hz,2H),5.30(s,2H);HRMS(ESI)m/z[M+H]+C9H6Cl5O2,计算值:320.8805,实测值:320.8815.
实施例7:4-溴丁酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用4-溴丁酸代替溴乙酸。(收率61%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),4.99(s,2H),3.40(t,J=7.4Hz,2H),2.52(t,J=7.2Hz,2H),2.17-2.08(m,2H);HRMS(ESI)m/z[M+H]+C9H6Cl5O2,计算值:324.9392,实测值:324.9391.
实施例8:4-氯苯甲酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用4-氯苯甲酸代替溴乙酸。(收率69%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.97(d,J=8.7Hz,2H),7.61(d,J=8.5Hz,2H),7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),4.99(s,2H);HRMS(ESI)m/z[M+H]+C14H10Cl3O2,计算值:314.9741,实测值:314.9740.
实施例9:4-甲氧基苯甲酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用4-甲氧基苯甲酸代替溴乙酸。(收率68%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:8.10(d,J=8.9Hz,2H),7.25(t,J=1.8Hz,1H),7.20(d,J=8.9Hz,2H),7.16(d,J=1.8Hz,2H),4.99(s,2H),3.89(s,3H);HRMS(ESI)m/z[M+H]+C15H13Cl2O3,计算值:311.0236,实测值:311.0231.
实施例10:3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3-(二氟甲基)-1-甲基-1H-吡唑-4-羧酸代替溴乙酸。(收率62%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:8.71(s,1H),7.29(t,J=56Hz,1H),7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),5.21(s,2H),3.82(s,3H);HRMS(ESI)m/z[M+H]+C13H11Cl2O2N2F2,计算值:335.0160,实测值:335.0161.
实施例11:2,2,2-三氟乙酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用三氟乙酸代替溴乙酸。(收率61%,无色液体)。1H NMR(400MHz,CDCl3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),5.21(s,2H);HRMS(ESI)m/z[M+H]+C9H6Cl2O2F3,计算值:272.9691,实测值:272.9692.
实施例12:N-(3,5-二氯苯基)-2,2,2-三氟乙酰胺的制备
目标化合物的合成与实施例1类似,不同点在于,用三氟乙酸代替溴乙酸,用3,5-二氯苯胺替代3,5-二氯苄醇。(收率68%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H);HRMS(ESI)m/z[M+H]+C8H5Cl2ONF3,计算值:257.9695,实测值:257.9691.
实施例13:2,2,2-三氟乙酸-3,5-二氯苯酯的制备
目标化合物的合成与实施例1类似,不同点在于,用三氟乙酸代替溴乙酸,用3,5-二氯苯酚替代3,5-二氯苄醇。(收率61%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H);HRMS(ESI)m/z[M+H]+C8H4Cl2O2F3,计算值:258.9535,实测值:258.9531.
实施例14:2,2,2-三氟乙酸-3,5-二氯苯乙酯的制备
目标化合物的合成与实施例1类似,不同点在于,用三氟乙酸代替溴乙酸,用3,5-二氯苯乙醇替代3,5-二氯苄醇。(收率63%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),4.12(t,J=6.8Hz,2H),3.50(t,J=6.8Hz,2H),;HRMS(ESI)m/z[M+H]+C10H8Cl2O2F3,计算值:286.9848,实测值:286.9841.
实施例15:4-三氟甲氧基苯甲酸-3,5-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用4-三氟甲氧基苯甲酸代替溴乙酸(收率63%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.91(d,J=8.7Hz,2H),7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),7.04(d,J=8.5Hz,2H),5.01(s,2H),;HRMS(ESI)m/z[M+H]+C15H10Cl2O3F3,计算值:364.9954,实测值:364.9953.
实施例16:4-三氟甲氧基苯甲酸-3,5-二氯苯酯的制备
目标化合物的合成与实施例1类似,不同点在于,用4-三氟甲氧基苯甲酸代替溴乙酸,用3,5-二氯苯酚替代3,5-二氯苄醇(收率71%,黄色固体)。1H NMR(400MHz,CDCl3d)δ:7.91(d,J=8.7Hz,2H),7.25(t,J=1.8Hz,1H),7.16(d,J=1.8Hz,2H),7.04(d,J=8.5Hz,2H);HRMS(ESI)m/z[M+H]+C14H8Cl2O3F3,计算值:350.9797,实测值:350.9781.
实施例17:3,3,3-三氟丙酸-3,5-二甲基苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3,3,3-三氟丙酸代替溴乙酸,用3,5-二甲基苄醇替代3,5-二氯苄醇(收率50%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.02(s,1H),7.00(s,2H),5.28(s,2H),3.26(q,J=10.0Hz,2H),2.33(s,6H);HRMS(ESI)m/z[M+H]+C12H14O2F3,计算值:247.0940,实测值:247.0941.
实施例18:3,3,3-三氟丙酸-3,5-二甲氧基苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3,3,3-三氟丙酸代替溴乙酸,用3,5-二甲氧基苄醇替代3,5-二氯苄醇(收率50%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:6.45-6.41(m,3H),5.36(s,2H),3.78(s,6H),3.26(q,J=10.0Hz,2H);HRMS(ESI)m/z[M+H]+C12H14O4F3,计算值:279.0839,实测值:279.0831.
实施例19:3,3,3-三氟丙酸-3,5-二溴苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3,3,3-三氟丙酸代替溴乙酸,用3,5-二溴苄醇替代3,5-二氯苄醇(收率52%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.58(t,J=1.7Hz,1H),7.43-7.39(m,2H),4.44(s,2H),3.26(q,J=10.0Hz,2H);HRMS(ESI)m/z[M+H]+C10H8O3F3Br2,计算值:374.8838,实测值:374.8831.
实施例20:3,3,3-三氟丙酸-2,4-二氯苄酯的制备
目标化合物的合成与实施例1类似,不同点在于,用3,3,3-三氟丙酸代替溴乙酸,用2,4-二氯苄醇替代3,5-二氯苄醇(收率53%,黄色液体)。1H NMR(400MHz,CDCl3 d)δ:7.40(d,J=8.3Hz,1H),7.35(d,J=2.1Hz,1H),7.24(dd,J=8.3,2.0Hz,1H),4.71(s,2H),3.26(q,J=10.0Hz,2H);HRMS(ESI)m/z[M+H]+C10H8O2F3Cl2,计算值:286.9848,实测值:286.9842.
采用实施例1-20类似的方法,合成表1中的其他化合物。
实施例21:本发明化合物的抗菌活性测试
寄主作物分别为黄瓜(品种为新泰密刺),小麦(品种为辽春10号),玉米(金黄糯2号)。
称取新化合物0.0088g溶解入2ml丙酮中,加入含0.1%吐温80的水,配制成400mg/L的药液20ml。另配制对照药,嘧菌酯药液20ml,用于活体筛选。
温室培养的两叶期黄瓜苗作为黄瓜霜霉病的试验寄主植物,两叶期小麦苗作为小麦白粉病的试验寄主植物,两叶期玉米苗作为玉米锈病的试验寄主植物。
喷雾器类型为立体作物喷雾机,喷雾压力为1.5kg/cm2,喷液量约为1000L/hm2,处理上述试验材料,然后自然风干,24h后接种病原菌。
采用接种器分别将黄瓜霜霉病菌孢子囊悬浮液(5×105个/ml)、玉米锈病菌孢子悬浮液(5×106个/ml)喷雾于寄主作物上,移入人工气候室培养(24℃,RH>90,无光照)。黄瓜霜霉病和玉米锈病的试验材料培养24h后,移置温室正常管理,4d后调查化合物的杀菌活性。
将白粉病菌孢子抖落在小麦叶片上,并在温室内培养,7d后调查化合物的杀菌活性。
结果调查参照美国植病学会编写的《A Manual of Assessment Keys for PlantDiseases》,用100~0来表示,以“100”级代表无病和“0”级代表最严重的发病程度。
实施例22:本发明化合物的抗菌活性测试
取新化合物溶解入1ml中二甲亚砜,配制成2000mg/L的药液。另配制对照药剂啶菌噁唑和啶酰菌胺25mg/L的药液1ml,用于离体筛选。
在预先培养好的水稻纹枯病和黄瓜灰霉病菌种平皿中,加入去离子水,轻轻刮取菌丝表面孢子,用3-5层纱布过滤,然后放入离心管,低速离心(1000rpm)5分钟,倒去上清液,再加入去离子水,再离心。将已沉淀的孢子,用适当量的去离子水将孢子稀释至100倍显微镜下有100个左右孢子的孢子悬浮液。
将配制好的的药液加入到96孔培养板上,每个药剂4次重复,每孔1μL。之后加入配制好的孢子悬浮液,每孔加入79μL,水稻纹枯病置于28℃黑暗培养箱中培养18h,黄瓜灰霉病置于18℃黑暗培养箱中培养18h,之后调查。
各化合物的抗菌结果如表1所示。
表1式(I)化合物的抗菌活性
实施例23:含有本发明化合物杀菌剂的组合物
(a)微乳剂
按比例准备以下组分:5.0%(重量百分比,下同)化合物I-1~I-201中任一种化合物(表1);30.0%聚乙烯吡咯烷酮-乙酸乙烯酯共聚物;30.0%烷基多苷;15.0%油酸甘油酯;20.0%水。
(b)可湿性粉剂
按比例准备以下组分:65.0%化合物I-1~I-201中任一种化合物(表1);2.0%十二烷基苯酚聚乙二醇醚;4.0%木质素磺酸钠;6.0%硅酸铝钠;23.0%蒙脱石(煅烧过的)。
(c)种子处理剂
按比例准备以下组分:20.00%化合物I-1~I-201中任一种化合物(表1);5.00%聚乙烯吡咯烷酮-乙酸乙烯酯共聚物;5.00%褐煤酸蜡;1.00%木质素磺酸钙;1.00%聚氧乙烯/聚氧丙烯嵌段共聚物;2.00%硬脂醇(POE 20);0.20%聚有机硅;0.05%着色剂红色染料;65.75%水。
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)
1.一种具有通式(I)所示结构的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐,
式中,T为H、氰基或者取代或未取代的选自下组的基团:C1-C8烷基、C2-C6烯基、C3-C6环烷基、C2-C6烯氧基、C2-C6炔基、C2-C6炔氧基、C1-C6烷氧基、C3-C6环烷氧基、C5-C7环烯基、4-8元杂环基、C6-C10芳基、-OC(=O)(C6-C10芳基)、-OC(=O)(C6-C10芳基)(C2-C6烯基)、-OC(=O)(C1-C8亚烷基)(C6-C10芳基)、-OC(=O)(C1-C8亚烷基)苯基(C2-C6烯基)、4-8元杂芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C8烷基、C3-C6环烷基、C1-C8卤代烷基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)C1-C8烷基、-C(=O)C3-C6环烷基、-C(=O)C1-C8卤代烷基、-C(=O)C6-C10芳基、-C(=O)4-8元杂芳基、-C(=O)4-8元杂环基;其中所述取代是指被选自下组的一个或多个基团取代:氰基、羟基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C8烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)O(C1-C8烷基)或C1-C6硫代烷基;
Z为O或NR2;其中,R2为氢、或者取代或未取代的选自下组的基团:C1-C8烷基、C2-C6烯基、C3-C6环烷基、C2-C6烯氧基、C2-C6炔基、C2-C6炔氧基、C1-C6烷氧基、C3-C6环烷氧基、C5-C7环烯基、4-8元杂环基、C6-C10芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基);其中所述取代是指被选自下组的一个或多个基团取代:卤素(氟、氯、溴)、氰基、C1-C8烷基、C1-C8卤代烷基、硝基、羟基、C2-C6烯基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基或C1-C6硫代烷基。
R1为取代或未取代的选自下组的基团:C1-C10烷基、C2-C6烯基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C10环烷基、-(C1-C8亚烷基)(C3-C10环烷基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(4-8元杂环基)、-C(=O)(C6-C10芳基)、-C(=O)(4-8元杂芳基)、-C(=O)(C1-C10烷基)、-C(=O)(C3-C6环烷基)、-C(=O)(4-8元杂环基)、-C(=O)(C6-C10芳基)NHC(=O)(4-10元杂芳基)、-(C6-C10芳基)(C6-C10芳基)NHC(=O)(4-10元杂芳基)、-(C6-C10芳基)NHC(=O)(4-10元杂芳基)、-C(=O)NRcRd、-NRcRd;其中Rc、Rd各自独立地选自:氢、C1-C8烷基、C3-C6环烷基、C1-C8卤代烷基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(O)(C6-C10芳基)、-C(O)(4-8元杂芳基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C8烷基、卤素(氟、氯、溴)、C1-C8卤代烷基、卤代4-8元杂芳基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C8烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-O(C6-C10芳基)或C1-C6硫代烷基。
2.如权利要求1所述的化合物,其特征在于,T为H、或者为取代或未取代的选自下组的基团:C1-C6烷基、C2-C6烯基、C3-C6环烷基、5-7元杂环基、苯基、5-7元杂芳基、-(C1-C8亚烷基)(4-10元杂芳基)、-(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHC(=O)(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C8烷基、C3-C6环烷基、C1-C8卤代烷基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、-C(=O)C1-C8烷基、-C(=O)C3-C6环烷基、-C(=O)C1-C8卤代烷基、-C(=O)C6-C10芳基、-C(=O)4-8元杂芳基、C(=O)4-8元杂环基;其中所述取代是指被选自下组的一个或多个基团取代:氰基、羟基、氧代(=O)、C1-C8烷基、氟、氯、溴、C1-C6卤代烷基、-C(=O)NH(C1-C8烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、C2-C6炔基、苯基、4-8元杂芳基、5-7元杂环基、-C(=O)O(C1-C8烷基)或C1-C6硫代烷基。
3.如权利要求1所述的化合物,其特征在于,Z为O或NR2;其中,R2为H、或者为取代或未取代的选自下组的基团:-(C1-C4亚烷基)(5-7元杂芳基)、-(C1-C4亚烷基)(C6-C10芳基)、-(C1-C4亚烷基)(C3-C6环烷基)、-(C1-C4亚烷基)(4-10元杂环基)、-(C1-C4亚烷基)NHC(=O)(4-10元杂芳基);其中所述取代是指被选自下组的一个或多个基团取代:卤素(氟、氯、溴)、氰基、C1-C4烷基、C1-C4卤代烷基、硝基、羟基、C2-C4烯基、C2-C4炔基、C6-C10芳基、4-8元杂芳基、4-8元杂环基、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基或C1-C4硫代烷基。
4.如权利要求1所述的化合物,其特征在于,R1为取代或未取代的选自下组的基团:C1-C6烷基、C2-C4烯基、C2-C4炔基、苯基、5-7元杂芳基、5-7元杂环基、C3-C8环烷基、-(C1-C6亚烷基)(C3-C8环烷基)、-(C1-C6亚烷基)苯基、-(C1-C6亚烷基)(4-10元杂芳基)、-(C1-C6亚烷基)(5-7元杂环基);其中所述取代是指被选自下组的一个或多个基团取代:氰基、氧代(=O)、C1-C6烷基、氟、氯、溴、C1-C4卤代烷基、卤代5-7元杂芳基、-C(=O)NH(C1-C6烷基)、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C2-C6烯基、硝基、羟基、C2-C6炔基、苯基、4-8元杂芳基、4-8元杂环基、-O-苯基或C1-C6硫代烷基。
5.如权利要求1所述的化合物,其特征在于,所述化合物为表1中的任一化合物。
6.一种农药组合物,其特征在于,包含:
(a)权利要求1-5中任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐、或者它们的组合;以及
(b)农药学上可接受的载体和/或赋形剂。
7.如权利要求6所述的农药组合物,其特征在于,所述农药组合物还包括:氟吗啉、炼酰吗啉、叶枯酞、磺菌胺、甲磺菌胺、噻氟菌胺、环氟菌胺、链噻菌胺、吡噻菌胺、环酰菌胺、苯酰菌胺、环丙酰菌胺、噻酰菌胺、氰菌胺、双氯氰菌胺、高效甲霜灵、高效苯霜灵、萎锈灵、呋吡酰胺、甲呋酰胺、氟酰胺、嘧菌酯、肟菌酯、啶氧菌酯、唑菌胺酯、氟嘧菌酯、烯肟菌酯、苯氧菌胺、烯肟菌胺、嘧菌胺、肟嘧菌胺、唪菌灵、氟菌唑、高效抑霉唑、咪唑菌酮、氰霜唑、抑霉唑、咪鲜胺、恶咪唑、麦穂宁、稻瘟酯、氧环唑、氟环唑、氟喹唑、苯醚甲环唑、四氟醚唑、戊唑醇、氟硅畔、硅氟唑、三唑醉、联苯三唑醉、环丙唑醇、高效烯唑醇、烯唑醇、粉唑醇、己唑醇、丙硫菌唑、灭菌唑、戊菌唑、腈菌唑、腈苯唑、亚胺唑、糖菌唑、种菌唑、叶菌唑;噻唑类:噻唑菌胺、苯噻硫氰、辛噻酮、多菌灵、十二环吗啉、丁苯吗啉、十三吗啉;吡咯类:拌种咯、咯菌腈、氟啶胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、环啶菌胺、啶斑肟、嘧啶环胺、氯苯嘧啶醇、氟苯嘧啶醇、嘧霉胺、嘧菌腙、嘧菌胺、氟嘧菌胺、灭螨猛、二氰蒽醌、乙氧喹啉、8-羟基喹啉、丙氧喹啉、苯氧喹啉、异丙菌胺、乙霉威、苯噻菌胺、霜霉威、硫菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯灵、梧宁霉素、灭瘟素、春雷霉素、多抗霉素、多氧霉素、活化酯、吲哚酯、溴硝醇、苯磺菌胺、甲苯磺菌胺、螺环菌胺、嗪胺灵、敌磺钠、戊菌隆、四氯苯酞、三环唑、烯丙苯噻唑、苯锈啶、氯硝胺、双胍辛胺、多果定、霜服氛、略嗤嗣、苯囷嗣、嗤囷嗣、啦囷嗣、链霉素、甲霜灵、丙森梓、苯霜灵、叶枯哩、有效霉素、井冈霉素、五氯硝基苯、代森锰锌、三乙膦酸铝、乙嘧酚磺酸酯、乙嘧酚、二甲嘧酚、三唑酮、甲基硫菌灵、多菌灵、苯菌灵、克菌丹、敌菌丹、灭锈胺、灭菌丹、呋酰胺、氟氯菌核利、乙烯菌核利、菌核净、福美双、稻瘟灵、稻瘟净、百菌清、硫磺、波尔多液、氢氧化锏、氧化亚铜、氧氣化铜、硫酸铜、苦参碱、蛇床子素、虎杖提取物、樟脑、腐殖酸铜、松脂酸铜(钠)、混合氨基酸铜、琥胶肥酸铜、柠檬酸铜、丁子香酚、香芹酚、小檗碱、乙蒜素、几丁聚糖、低聚糖素、葡聚烯糖、大蒜素。
8.如权利要求1-5中任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐或者如权利要求6所述的农药组合物的用途,其特征在于,用于制备杀菌剂。
9.如权利要求8所述的用途,其特征在于,所述杀菌剂防治以下病害:黄瓜炭疽病,霜霉病(黄瓜霜霉病、油菜霜霉病、大豆霜霉病、甜菜霜霉病、甘蔗霜霉病、烟草霜霉病、豌豆霜霉病、丝瓜霜霉病、冬瓜霜霉病、甜瓜霜霉病、白菜霜霉病、菠菜霜霉病、萝卜霜霉病、葡萄霜霉病、葱霜霉病),白锈菌(油菜白锈菌、白菜白锈菌),猝倒病(油菜猝倒病、烟草猝倒病、番茄猝倒病、辣椒猝倒病、茄子猝倒病、黄瓜猝倒病、棉苗猝倒病)、绵腐病(辣椒绵腐病、丝瓜绵腐病、冬瓜绵腐病),疫病(蚕豆疫病、黄瓜疫病、冬瓜疫病、西瓜疫病、甜瓜疫病、辣椒疫病、韭菜疫病、大蒜疫病、棉花疫病),晚疫病(马铃磐晚疫病、番茄晚疫病)等;根腐病(辣椒根腐病、茄子根腐病、菜豆根腐病、黄瓜根腐病、苦瓜根腐病、棉花根腐病、蚕豆根腐病),立枯病(棉苗立枯病、芝麻立枯病、辣椒立枯病、黄瓜立枯病、白菜立枯病),黄萎病(棉花黄萎病、向日葵黄萎病、番茄黄萎病、辣椒黄萎病、茄子黄萎病),黑星病(西葫芦黑星病、冬瓜黑星病、甜瓜黑星病),灰霉病(棉铃黑灰霉病、红麻灰霉病、番茄灰霉病、辣椒灰霉病、菜豆灰霉病、韭菜灰霉病、猕猴桃灰霉病、草莓灰霉病、黄瓜灰霉病),褐斑病(棉花褐斑病、黄麻褐斑病、甜菜褐斑病、花生褐斑病、辣椒褐斑病、冬瓜褐斑病、大豆褐斑病、向日葵褐斑病、豌豆褐斑病、蚕豆褐斑病),黑斑病(亚麻假黑斑病、油菜黑斑病、芝麻黑斑病、向日葵黑斑病、蓖麻黑斑病、番茄黑斑病、辣椒黑斑病、茄子黑斑病、菜豆黑斑病、黄瓜黑斑病、芹菜黑斑病、胡萝卜黑斑病、苹果黑斑病、花生黑斑病),斑枯病(番茄斑枯病、辣椒斑枯病、芹菜斑枯病),早疫病(番茄早疫病、辣椒早疫病、茄子早疫病、马铃薯早疫病、芹菜早疫病),轮纹病(大豆轮纹病、芝麻轮纹病、菜豆轮纹病),叶枯病(芝麻叶枯病、向日葵叶枯病、西瓜叶枯病、甜瓜叶枯病),茎基腐病(番茄茎基腐病、菜豆茎基腐病),及其他(玉米圆斑病、稻瘟病、粟黑鞘病、甘蔗眼斑病、棉铃曲苒病、花生冠腐病、大豆茎腐病、大豆黑点病、甜瓜大斑病、花生网斑病、茶赤叶斑病、辣椒白星病、冬瓜叶斑病、芽菜黑腐病、疲菜心腐病、红麻叶霉病、红麻斑点病、黄麻茎斑病、大豆紫斑病、芝麻叶斑病、蓖麻灰斑病、茶褐色叶斑病、茄子褐色圆星病、菜豆红斑病、苦瓜白斑病、西瓜斑点病、黄麻枯腐病、向日葵根茎腐病、菜豆碳腐病、茄子棒叶斑病、黄瓜靶斑病、番茄叶霉病、茄子叶霉病、蚕豆赤斑病)等:担子菌病害,如锈病(小麦条锈病、小麦秆锈病、小麦叶锈病、花生锈病、向日葵锈病、甘鹿锈病、韭菜锈病、葱锈病、栗锈病、大豆锈病、玉米锈病),黑穗病(玉米丝黑穗病、玉米黑粉病、高粱丝黑穗病、高粱散黑穂病、高粱坚黑穗病、高粱柱黑粉病、粟粒黑穂病、甘蔗黑穂病、菜豆锈病)及其他(如小麦纹枯病、水稻纹枯病等)等;子囊菌病害,如白粉病(小麦白粉病、生菜白粉病、芝麻白粉病、向日葵白粉病、甜菜白粉病、茄子白粉病、豌豆白粉病、丝瓜白粉病、南瓜白粉病、西葫芦白粉病、冬瓜白粉病、甜瓜白粉病、葡萄白粉病、蚕豆白粉病),菌核病(亚麻菌核病、油菜菌核病、大豆菌核病、花生菌核病、烟草菌核病、辣椒菌核病、茄子菌核病、菜豆菌核病、豌豆菌核病、黄瓜菌核病、苦瓜菌核病、冬瓜菌核病、西瓜菌核病、芹菜菌核病),黑星病(苹果黑星病、梨黑星病),根肿病(甘蓝根肿病、白菜根肿病、花椰菜根肿病、撇蓝根肿病、芥菜根肿病、萝卜根肿病、芜菁根肿病、油菜根肿病)。
10.一种防治植物病菌的方法,其特征在于,包括给植物施用权利要求1-5中任一所述的化合物,其光学异构体、顺反异构体或其农药学上可接受的盐或者如权利要求6所述的农药组合物。
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