CN111057024A - 悉尼酮与悉尼酮亚胺类化合物及其制备方法和用途 - Google Patents
悉尼酮与悉尼酮亚胺类化合物及其制备方法和用途 Download PDFInfo
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- CN111057024A CN111057024A CN201911347375.4A CN201911347375A CN111057024A CN 111057024 A CN111057024 A CN 111057024A CN 201911347375 A CN201911347375 A CN 201911347375A CN 111057024 A CN111057024 A CN 111057024A
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- membered heteroaryl
- alkyl
- alkylene
- cycloalkyl
- radical
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- 238000002360 preparation method Methods 0.000 title abstract description 68
- 150000002466 imines Chemical class 0.000 title description 2
- -1 sydnone imine compounds Chemical class 0.000 claims abstract description 229
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- 201000010099 disease Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract description 21
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 77
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- 150000003839 salts Chemical class 0.000 claims description 19
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
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- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
-
- 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
-
- 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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
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- C—CHEMISTRY; METALLURGY
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6527—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and oxygen atoms as the only ring hetero atoms
- C07F9/653—Five-membered rings
- C07F9/65306—Five-membered rings containing two nitrogen atoms
Abstract
本发明公开了悉尼酮与悉尼酮亚胺类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
本发明涉及悉尼酮与悉尼酮亚胺类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。
悉尼酮或者悉尼酮亚胺类化合物为研究最为广泛的介离子类化合物,该结构的化合物具有广泛的生物活性,具有抗癌,抗病毒,止痛,解痉挛,退热,自由基清除及一氧化氮供体的生物活性。尚需进一步开发。
发明内容
本发明的目的是提供一类结构新颖的含悉尼酮或悉尼酮亚胺结构的化合物,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,L为H、卤素(如氟、氯、溴、碘)、羟基、硝基、羧基、氰基、SHSF5、SCN、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、-CONRaRb、C6-C10芳基、-C(O)(C6-C10芳基)、-COO(C6-C10芳基)、-COO(C6-C10芳基)(C2-C6烯基)、-COO(C1-C8亚烷基)(C6-C10芳基)、-COO(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)、-C(O)(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-C(O)(C1-C8烷基)、-C(O)(4-8元杂芳基)、-C(O)(4-8元杂环基)、-C(O)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHCO(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;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、-CONH(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、-COO(C1-C8烷基)或C1-C6硫代烷基;
Q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、-(C1-C8亚烷基)(C3-C6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)、-COO(C6-C10芳基)、-COO(4-8元杂芳基)、-COO(C1-C10烷基)、-COO(C3-C6环烷基)、-COO(4-8元杂环基)、-C(O)(C6-C10芳基)NHCO(4-10元杂芳基)、-(C6-C10芳基)(C6-C10芳基)NHCO(4-10元杂芳基)、-(C6-C10芳基)NHCO(4-10元杂芳基)、-CONRcRd、-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、-CONH(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;
M为O-或N-R1;其中,R1为取代或未取代的选自下组的基团:-COO(C1-C8烷基)、-SO2(C1-C8烷基)、-C(O)(C1-C8烷基)、-C(O)(C6-C10芳基)、-SO2(C6-C10芳基)、-C(O)(4-8元杂芳基)、-P(O)(OC1-C8烷基)(OC1-C8烷基)、-CO(C1-C8亚烷基)(4-8元杂环基)、-COO(C6-C10芳基)、-COO(4-8元杂芳基)、-COO(C3-C8环烷基)、-COO(4-8元杂环基)、-SO2(C3-C8环烷基)、-SO2(4-8元杂芳基)、-SO2(4-8元杂环基)、-C(O)(C3-C8环烷基)、-C(O)(4-8元杂环基)、-CO(C1-C8亚烷基)(C3-C8环烷基)、-CO(C1-C8亚烷基)(C6-C10芳基)、-CO(C1-C8亚烷基)(4-8元杂芳基)、-CO(C1-C8亚烷基)(C3-C8环烷基)、-SO(C1-C8烷基)、-SO(C6-C10芳基)、-SO(C3-C8环烷基)、-SO(4-8元杂芳基)、-SO(4-8元杂环基)、-CONReRf,其中Re、Rf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;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,M为O-或N-R1;其中,R1为取代或未取代的选自下组的基团:-COO(C1-C6烷基)、-SO2(C1-C4烷基)、-C(O)(C1-C4烷基)、-C(O)苯基、-SO2苯基、-C(O)(5-6元杂芳基)、-P(O)(OC1-C4烷基)(OC1-C4烷基)、-CO(C1-C4亚烷基)(5-6元杂环基)、-COO苯基、-COO(5-6元杂芳基)、-COO(C3-C6环烷基)、-COO(5-6元杂环基)、-SO2(C3-C6环烷基)、-SO2(5-6元杂芳基)、-SO2(5-6元杂环基)、-C(O)(C3-C6环烷基)、-C(O)(5-6元杂环基)、-CO(C1-C4亚烷基)(C3-C6环烷基)、-CO(C1-C4亚烷基)苯基、-CO(C1-C4亚烷基)(5-6元杂芳基)、-CO(C1-C4亚烷基)(C3-C6环烷基)、-SO(C1-C4烷基)、-SO苯基、-SO(C3-C6环烷基)、-SO(5-6元杂芳基)、-SO(5-6元杂环基)、-CONReRf,其中Re、Rf独立地选自H、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、4-8元杂芳基、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: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、苯基、5-6元杂芳基、5-6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,R1为取代或未取代的选自下组的基团:-COO(C1-C6烷基)、-SO2(C1-C4烷基)、-C(O)(C1-C4烷基)、-C(O)苯基、-SO2苯基、-C(O)(5-6元杂芳基)、-P(O)(OC1-C4烷基)(OC1-C4烷基)、-CO(C1-C4亚烷基)(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:卤素(氟、氯、溴)、氰基、C1-C4烷基、C1-C4卤代烷基。
在另一优选例中,R1为-COO(C1-C6烷基)、卤素(氟)取代的或未取代的-SO2(C1-C4烷基)、卤素和/或氰基取代或未取代的-C(O)苯基、C1-C4烷基取代的或未取代的-SO2苯基、卤素(氟、氯)取代的或未取代的-C(O)(C1-C4烷基)、C1-C4烷基和C1-C4卤代烷基取代的或未取代的-C(O)(5-6元杂芳基)、-CO(C1-C4亚烷基)(5-6元杂环基)、-P(O)(OC1-C4烷基)(OC1-C4烷基)、卤素(氯)和/或C1-C4卤代烷基取代的-C(O)(5-6元杂芳基)、卤代烷基取代的-C(O)苯基。
在另一优选例中,R1为表1中列出的基团。
在另一优选例中,L为H、氟、氯、溴、碘、羟基、硝基、羧基、氰基、SHSF5、SCN、或者取代或未取代的选自下组的基团:C1-C4烷基、C2-C4烯基、C3-C6环烷基、C2-C4烯氧基、C2-C4炔基、C2-C4炔氧基、C1-C4烷氧基、C3-C6环烷氧基、C5-C6环烯基、5-6元杂环基、-CONRaRb、苯基、-C(O)苯基、-COO苯基、-COO苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基、5-6元杂芳基、-(C1-C4亚烷基)(4-10元杂芳基)、-(C1-C4亚烷基)苯基、-C(O)(C1-C4亚烷基)苯基、-(C1-C4亚烷基)(C3-C6环烷基)、-C(O)(C1-C4烷基)、-C(O)(5-6元杂芳基)、-C(O)(5-6元杂环基)、-C(O)(C3-C6环烷基)、-(C1-C4亚烷基)(5-10元杂环基)、-(C1-C4亚烷基)NHCO(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、5-6元杂芳基、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:氰基、羟基、氧代(=O)、C1-C4烷基、卤素(氟、氯、溴)、C1-C4卤代烷基、-CONH(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、C2-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-COO(C1-C4烷基)或C1-C4硫代烷基。
在另一优选例中,L为H、氟、氯、溴、碘或者取代或未取代的选自下组的基团:C1-C4烷基、-CONRaRb、苯基、-C(O)苯基、-COO苯基、-COO苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基、5-6元杂芳基、-(C1-C4亚烷基)(4-10元杂芳基)、-(C1-C4亚烷基)(5-10元杂环基)、-(C1-C4亚烷基)NHCO(4-10元杂芳基);其中Ra、Rb各自独立地选自H、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基;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-C4烷基、卤素(氟、氯、溴)、C1-C4卤代烷基、-CONH(C1-C4烷基)、C3-C6环烷基、C1-C4烷氧基、C1-C4卤代烷氧基、或-COO(C1-C4烷基)。
在另一优选例中,L为表1中列出的基团。
在另一优选例中,Q为取代或未取代的选自下组的基团:C2-C10烷基、C2-C5烯基、C2-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-(C1-C4亚烷基)(C3-C6环烷基)、-(C1-C4亚烷基)(苯基)、-(C1-C4亚烷基)(5-6元杂芳基)、-(C1-C4亚烷基)(5-6元杂环基)、-C(O)(苯基)、-C(O)(5-6元杂芳基)、-C(O)(C1-C4烷基)、-C(O)(C3-C6环烷基)、-C(O)(5-6元杂环基)、-COO(苯基)、-COO(5-6元杂芳基)、-COO(C1-C4烷基)、-COO(C3-C6环烷基)、-COO(5-6元杂环基)、-C(O)(苯基)NHCO(4-6元杂芳基)、-(苯基)(苯基)NHCO(4-6元杂芳基)、-(苯基)NHCO(4-6元杂芳基)、-CONRcRd、-NRcRd;其中Rc、Rd各自独立地选自:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、4-8元杂芳基、4-8元杂环基、-C(O)(苯基)、-C(O)(4-6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-C4烷基、氟、氯、溴、C1-C4卤代烷基、卤代4-6元杂芳基、-CONH(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-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-O(苯基)或C1-C4硫代烷基。
在另一优选例中,Q为取代或未取代的选自下组的基团:-(C1-C4亚烷基)(C3-C6环烷基)、-(C1-C4亚烷基)(苯基)、-(C1-C4亚烷基)(5-6元杂芳基)、-(C1-C4亚烷基)(5-6元杂环基)、-C(O)(苯基)、-C(O)(5-6元杂芳基)、-C(O)(C1-C4烷基)、-C(O)(C3-C6环烷基)、-C(O)(5-6元杂环基)、-COO(苯基)、-COO(5-6元杂芳基)、-COO(C1-C4烷基)、-COO(C3-C6环烷基)、-COO(5-6元杂环基)、-C(O)(苯基)NHCO(4-6元杂芳基)、-(苯基)(苯基)NHCO(4-6元杂芳基)、-(苯基)NHCO(4-6元杂芳基)、-CONRcRd、-NRcRd;其中Rc、Rd各自独立地选自:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、4-8元杂芳基、4-8元杂环基、-C(O)(苯基)、-C(O)(4-6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-C4烷基、氟、氯、溴、C1-C4卤代烷基、卤代4-6元杂芳基、-CONH(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-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-O(苯基)或C1-C4硫代烷基。
在另一优选例中,Q为表1中列出的基团。
在另一优选例中,R1为被一个或多个选自氢、卤素、氰基、硝基、羟基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6硫代烷基的取代基所取代的甲基羰基;较佳地为三氟甲基羰基。
在另一优选例中,L为氢、卤素、C1-C8烷基、五元或六元芳基、五元或六元杂芳基、五元或六元杂芳基胺基羰基、五元或六元杂环、五元或六元杂环基胺基羰基;上述基团任选被选自下组的基团单取代或多取代:氢、卤素、氰基、硝基、羟基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6硫代烷基。
在另一优选例中,L为被一个或多个选自氢、卤素、氰基、硝基、羟基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6硫代烷基的取代基所取代的苄基或苯基;较佳地为三氟甲氧基取代的苯基。
在另一优选例中,Q为C1-C8烷基、C1-C6卤代烷基、五元或六元芳基、五元或六元芳基-C1-C6烷基、五元或六元杂芳基、五元或六元杂芳基-C1-C6烷基、五元或六元杂环、五元或六元杂环基-C1-C6烷基;上述基团任选选自下组的一个或多个基团取代:氢、卤素、氰基、硝基、羟基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6硫代烷基。
在另一优选例中,Q为被一个或多个选自氢、卤素、氰基、硝基、羟基、C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C6环烷基、C1-C6烷氧基、C1-C6卤代烷基、C1-C6卤代烷氧基或C1-C6硫代烷基的取代基所取代的苄基或苯基;较佳地为3,5-三氯取代的苯基。
在另一优选例中,所述化合物为表1中的任一化合物。
在另一优选例中,M为O-,L为H时,A或Q不为以下基团:未取代的苯基或苄基、C1-C4烷基取代的苯基或苄基、硝基取代的苯基或苄基。
在另一优选例中,M为O-,A为苯基时,L不为以下基团:3-三氟甲基苯基、吡啶基、C1-C2烷氧基取代的苯基,硝基取代的苯基、三氟甲基、氧杂环丁烷基、4-甲基苯基、碘、酰胺基亚甲基、羧基亚甲基、酰肼基亚甲基、杂环酰基、噻唑基、锂、氯、甲磺酰基、吗啉基亚甲基酰基、吡啶基亚甲基酰基、氯亚甲基酰基、乙酰基、酰基和羟基取代的亚甲基、甲基亚磺酰基、硫醚基、甲氧基甲酰基、苯基、异丁基取代的苯基、取代氨基取代的苯基、酰胺基、羧基、N’N-二乙基甲基、N’N-二甲基甲基。
在另一优选例中,M为O-,L为乙酸基时,A不为以下基团:取代苯基,苄基。在另一优选例中,M为O-,L为酰胺基亚甲基时,A不为以下基团:取代苯基。在另一优选例中,M为O-,L为甲氧基乙酰基时,A不为以下基团:取代苯基。在另一优选例中,M为O-,A为4-甲基苯基时,L不为以下基团:甲酰基、溴。在另一优选例中,M为O-,A为甲氧基取代苯基时,L不为以下基团:溴乙基、溴、吗啉基亚甲基、苯基、N’N-二乙基甲基、N’N-二甲基乙基。在另一优选例中,M为O-,L为亚甲基吗啉基时,A不为以下基团:C1-C6烷基、苄基。在另一优选例中,M为O-,L为苯基时,A不为以下基团:N’N-二甲基甲基、吗啉亚甲基、哌啶亚甲基、四氢吡咯亚甲基、酰胺基、三甲基硅基、苯基和羟基取代的甲基、烯丙基、硝基取代苯基、4-氯苯基、羧基、硫醚基亚甲基、甲酸亚甲基、N’N-二乙基甲基、在另一优选例中,M为O-,L为硝基时,A不为以下基团:硝基取代苯基。在另一优选例中,M为O-,L为硝基取代苯基时,A不为以下基团:硝基取代苯基。在另一优选例中,M为O-,Q为丙基时,A不为以下基团:酰胺基。在另一优选例中,M为O-,Q为异丙基时,A不为以下基团:酰胺基。在另一优选例中,M为O-,L为苯基和羟基取代的甲基时,A不为以下基团:氨基取代的亚甲基。在另一优选例中,M为O-,A为氰基亚甲基时,L不为以下基团:溴、碘。在另一优选例中,M为O-,L为苯乙酰基时,A不为以下基团:氨基取代的亚甲基。在另一优选例中,M为O-,A为苯基亚甲基时,L不为以下基团:吗啉亚甲基。在另一优选例中,M为O-,A为N’N-二甲基乙基时,L不为以下基团:苯基亚甲基、4-甲氧基苯基。在另一优选例中,M为O-,A为N’N-二甲基甲基时,L不为以下基团:4-甲氧基苯基。在另一优选例中,M为O-,L为甲基时,A不为以下基团:N’N-二乙基甲基、N’N-二甲基乙基、哌啶亚甲基、四氢吡咯亚甲基、巯基亚甲基、苯基亚甲基、N’N-二甲基甲基亚甲基氧甲基、溴二硝基甲基、氯二硝基甲基、硫醚基亚甲基、苯基取代亚乙基、胺基磺酰基亚甲基、磺酰基亚甲基、亚磺酰基亚甲基、三硝基甲基、羧基、吗啉亚甲基。在另一优选例中,M为O-,L为叔丁基时,A不为以下基团:苯基取代亚乙基、硫醚基亚甲基。在另一优选例中,M为O-,L为溴时,A不为以下基团:酰胺基、取代苯乙酰基、十五烷基、乙氧基甲酰基、羧基。在另一优选例中,M为O-,L为氯时,A不为以下基团:羧基、酰胺基。在另一优选例中,M为O-,L为苯基亚甲基时,A不为以下基团:苯基亚甲基、氰基、乙氧基乙酰基、羧基、酰胺基、N’N-二甲基乙基。在另一优选例中,M为O-,A为丙基时,L不为以下基团:酯基。在另一优选例中,M为O-,L为羧基亚乙基时,A不为以下基团:氰基亚甲基。在另一优选例中,M为O-,A为酰胺基时,L不为以下基团:羟基和苯基取代的甲基、苯甲酰基、甲酯基亚乙基酰基。在另一优选例中,M为O-,A为甲氧基甲酰基时,L不为以下基团:取代酰基、取代羟基。在另一优选例中,M为O-,A为羧基时,L不为以下基团:硝基取代的苯基。在另一优选例中,M为O-,A为氰基亚甲基时,L不为以下基团:苄基、异丁基、甲基、苯基。在另一优选例中,M为O-,A、L不为以下基团:C1-C4烷基。
在另一优选例中,M为BocN-,A不为以下基团:C1-C4烷基、甲氧基亚甲基。在另一优选例中,M为苯甲酰基N-,A不为以下基团:甲氧基亚甲基、C1-C4烷基、苯基、酰胺基。在另一优选例中,M为乙酰基N-,A不为以下基团:C1-C4烷基、苯基。在另一优选例中,M为三氟乙酰基N-,A不为以下基团:C1-C4烷基。在另一优选例中,M为丁胺酰基N-,A不为以下基团:C1-C4烷基。在另一优选例中,M为甲胺酰基N-,A不为以下基团:酯基、酰胺基、苯基。在另一优选例中,M为甲氧基酰基N-,A不为以下基团:C1-C4烷基。在另一优选例中,M为苯胺酰基N-,A不为以下基团:酰胺基、酯基、羧基。
本发明的第二方面,提供一种农药组合物,包含:
(a)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%。
在需要的时候,在所述农药组合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。
在另一优选例中,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。
本发明的第三方面,提供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,或者第二方面所述的农药组合物的用途,用于防治植物病害或制备杀菌剂。
在另一优选例中,所述植物病害为植物真菌病害。
在另一优选例中,所述杀菌剂防治以下病害:炭疽病、霜霉病、白锈菌、猝倒病、绵腐病、疫病、晚疫病、根腐病、立枯病、黄萎病、黑星病、灰霉病、褐斑病、黑斑病、斑枯病、早疫病、轮纹病、叶枯病、茎基腐病、锈病、黑穗病、纹枯病、白粉病、菌核病、黑星病、根肿病。在另一优选例中,所述杀菌剂防治以下病害:炭疽病、霜霉病、灰霉病、锈病、纹枯病、白粉病。
在另一优选例中,所述杀菌剂防治以下病害:黄瓜炭疽病、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、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、小麦条锈病、小麦杆锈病、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、小麦纹枯病、水稻纹枯病、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。
本发明的第四方面,提供一种防治植物真菌病害的方法,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所述的农药组合物的步骤。
在另一优选例中,所述真菌病害选自:炭疽病、霜霉病、白锈菌、猝倒病、绵腐病、疫病、晚疫病、根腐病、立枯病、黄萎病、黑星病、灰霉病、褐斑病、黑斑病、斑枯病、早疫病、轮纹病、叶枯病、茎基腐病、锈病、黑穗病、纹枯病、白粉病、菌核病、黑星病、根肿病。
本发明合成含悉尼酮或悉尼酮亚胺的类似物,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。本发明含悉尼酮或悉尼酮亚胺的类似物,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。
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。说明书中所揭示的各个特征,可以被任何提供相同、均等或相似目的的替代性特征取代。限于篇幅,在此不再一一累述。
具体实施方式
本申请的发明人经过广泛而深入的研究,研发出一系列含有悉尼酮或悉尼酮亚胺结构的类似物,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。
术语
在本发明中,术语“C1-C8”是指具有1、2、3、4、5、6、7或8个碳原子,依此类推。“4-8元”是指具有4-8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,例如甲基、乙基、丙基、异丙基、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3-6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、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。
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“亚烷基”是指烷烃分子中少掉两个氢原子而成的基团。
术语“芳基”表示包含一个或多个芳环的烃基部分。例如术语“C6-C10芳基”是指在环上不含杂原子的具有6至10个碳原子的芳香族环基,如苯基、萘基等。
术语“杂芳基”表示包含1至4个杂原子的杂芳族体系,所述杂原子包括氮、氧和S(O)r(其中r是整数0、1、2)的杂原子,例如,4-8元杂芳基指含有4-8个环原子的杂芳族体系,4-10元杂芳基指含有4-10个环原子的杂芳族体系,包括但不限于吡咯基、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、苯并咪唑基、三唑基等。
术语“环系”指碳环或杂环。
术语“杂环基”指包含至少一个环杂原子(例如N,O或S)的环状基团。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。杂环基的例子包括但不限于吗啉基、六氢异吲哚基、四氢呋喃基、四氢吡咯基等。
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,如醋酸盐,苯甲酸盐等。
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1:3-(2-甲基-4-七氟异丙基苄基)悉尼酮的制备
1.1 2-(2-甲基-4-七氟异丙基苄基)氨基乙酸的制备
将10mmol的4-七氟异丙基苄胺溶解在80ml丙酮中,加入10mmol的氯乙酸和50g无水碳酸钾。过夜加热回流反应,TLC追踪反应。过滤反应液,滤液旋蒸后,通过柱层析得到2-(2-甲基-4-七氟异丙基苯基)氨基乙酸(收率72%,淡黄色液体)。1H NMR(400MHz,CDCl3 d)δ:7.36(m,2H),7.21(m,2H),3.79(s,2H),3.49(s,2H);HRMS(ESI)m/z[M+H]+C12H11F7NO2,计算值:334.0415,实测值:334.0419.
1.2 3-(4-七氟异丙基苄基)悉尼酮的制备
将13.81mmol 2-(2-甲基-4-七氟异丙基苯基)氨基乙酸溶解在150ml无水四氢呋喃中,在0℃氩气保护下,逐滴加入20.71mmol亚硝酸叔丁酯。反应在1小时内逐步回升到室温,TLC追踪反应。反应结束后,加入15mmol的三氟乙酸酐,在室温下搅拌1小时,TLC追踪反应。反应结束后,加入乙酸乙酯/水淬灭反应,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-(2-甲基-4-七氟异丙基苯基)悉尼酮(收率73%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.76(s,1H),7.28(m,2H),7.20(m,2H),2.29(s,2H);HRMS(ESI)m/z[M+H]+C12H8F7N2O2,计算值:345.1928,实测值:345.1930.
实施例2:3-(4-三氟甲基苄基)悉尼酮的制备
2.1 4-(三氟甲基苄基)氨基乙酸的制备
将10mmol的4-三氟甲基苄胺溶解在80ml丙酮中,加入10mmol的氯乙酸和50g无水碳酸钾。过夜加热回流反应,TLC追踪反应。过滤反应液,滤液旋蒸后,通过柱层析得到4-(三氟甲基苄基)氨基乙酸(收率75%,淡黄色液体)。1H NMR(400MHz,CDCl3 d)δ:12.59(s,1H),7.49(m,2H),7.15(m,2H),4.10(s,1H),3.9(s,2H),3.29(s,2H);HRMS(ESI)m/z[M+H]+C10H11F3NO2,计算值:234.1907,实测值:234.1908.
2.2 3-(4-三氟甲基苄基)悉尼酮的制备
将13.81mmol 4-(三氟甲基苄基)氨基乙酸溶解在150ml无水四氢呋喃中,在0℃氩气保护下,逐滴加入20.71mmol亚硝酸叔丁酯。反应在1小时内逐步回升到室温,TLC追踪反应。反应结束后,加入15mmol的三氟乙酸酐,在室温下搅拌1小时,TLC追踪反应。反应结束后,加入乙酸乙酯/水淬灭反应,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-(4-三氟甲基苄基)悉尼酮(收率65%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.76(s,1H),7.45(m,2H),7.10(m,2H),2.29(s,2H);HRMS(ESI)m/z[M+H]+C10H8F3N2O2,计算值:245.1752,实测值:245.1730.
实施例3:3-(3-三氟甲基苄基)悉尼酮
3.1 3-(三氟甲基苄基)氨基乙酸的制备
将10mmol的3-三氟甲基苄胺溶解在80ml丙酮中,加入10mmol的氯乙酸和50g无水碳酸钾。过夜加热回流反应,TLC追踪反应。过滤反应液,滤液旋蒸后,通过柱层析得到3-(三氟甲基苄基)氨基乙酸(收率76%,淡黄色液体)。1H NMR(400MHz,CDCl3 d)δ:13.00(s,1H),7.45-7.53(m,3H),7.28(m,1H),4.12(s,1H),3.80(s,2H),3.19(s,2H);HRMS(ESI)m/z[M+H]+C10H11F3NO2,计算值:234.1907,实测值:234.1909.
3.2 3-(3-三氟甲基苄基)悉尼酮的制备
将13.81mmol 3-(三氟甲基苄基)氨基乙酸溶解在150ml无水四氢呋喃中,在0℃氩气保护下,逐滴加入20.71mmol亚硝酸叔丁酯。反应在1小时内逐步回升到室温,TLC追踪反应。反应结束后,加入15mmol的三氟乙酸酐,在室温下搅拌1小时,TLC追踪反应。反应结束后,加入乙酸乙酯/水淬灭反应,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-(3-三氟甲基苄基)悉尼酮(收率67%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.76(s,1H),7.47(s,1H),7.45(s,1H),7.43(m,1H),7.41(m,1H),2.29(s,2H);HRMS(ESI)m/z[M+H]+C10H8F3N2O2,计算值:245.1752,实测值:245.1731.
实施例4:3-(5-氯呋喃-2-甲基)悉尼酮的制备
4.1 2-(5-氯呋喃甲基氨基)-2-苯乙酸的制备
将10mmol的2-(5-氯呋喃)甲胺溶解在50ml乙酸乙酯中,加入10mmol的α-溴苯乙酸和10mmol的三乙胺。过夜加热回流反应,TLC追踪反应。反应结束后加水,使用乙酸乙酯萃取,之后使用饱和氯化钠溶液洗,分离得到有机相,旋蒸后,通过柱层析得到:2-(5-氯呋喃甲基氨基)-2-苯乙酸(收率60%,淡红色液体)。1H NMR(400MHz,CDCl3 d)δ:12.69(s,1H),6.39(m,1H),6.29(m,1H),4.16(s,1H),4.92(s,1H),3.66(s,1H),3.49(s,2H);HRMS(ESI)m/z[M+H]+C7H9NClO3,计算值:190.0602,实测值:190.0603.
4.2 3-(5-氯呋喃-2-甲基)悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-(5-氯呋喃甲基氨基)-2-苯乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率66%,淡黄色固体)。1HNMR(400MHz,CDCl3 d)δ:7.76(m,1H),6.33(m,1H),6.10(m,1H),2.10(s,2H);HRMS(ESI)m/z[M+H]+C7H6N2ClO3,计算值:201.1452,实测值:201.1420.
实施例5:3-(吡啶-4-甲基)-4-苯基悉尼酮的制备
5.1 2-苯基-2-(4-吡啶基甲基氨基)乙酸的制备
将20mmol的4-甲氨基吡啶溶解在50ml乙醚中,加入10mmol的α-溴苯乙酸。过夜加热回流反应,TLC追踪反应。反应结束后加水,过滤可得:2-苯基-2-(4-吡啶基甲基氨基)乙酸(收率80%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:12.69(s,1H),8.55(m,2H),7.25-7.35(m,6H),5.01(s,1H),4.65(s,1H),4.20(s,2H);HRMS(ESI)m/z[M+H]+C14H15N2O2,计算值:243.2803,实测值:243.2805.
5.2 3-(吡啶-4-甲基)-4-苯基悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-苯基-2-(4-吡啶基甲基氨基)乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率70%,淡黄色固体)。1HNMR(400MHz,CDCl3 d)δ:8.53(m,2H),7.68(m,2H),7.55(m,1H),7.53(m,2H),7.22(m,2H)2.29(s,2H);HRMS(ESI)m/z[M+H]+C14H12N3O2,计算值:254.2612,实测值:254.2622.
实施例6:3-对三氟甲氧基苄基-4-苯基悉尼酮的制备
6.1 2-(4-三氟甲氧基苄基氨基)-2-苯乙酸的制备
将20mmol的对三氟甲氧基苄胺溶解在50ml乙醚中,加入10mmol的α-溴苯乙酸。过夜加热回流反应,TLC追踪反应。反应结束后加水,过滤可得:2-(4-三氟甲氧基苄基氨基)-2-苯乙酸(收率85%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:12.65(s,1H),7.25-7.33(m,5H),7.13(m,2H),6.89(m,2H),4.92(s,1H),4.70(s,1H),3.80(s,2H);HRMS(ESI)m/z[M+H]+C16H13NO3F3,计算值:326.1314,实测值:326.1312.
6.2 3-对三氟甲氧基苄基-4-苯基悉尼酮的制备
将13.81mmol 2-(4-三氟甲氧基苄基氨基)-2-苯乙酸溶解在150ml无水四氢呋喃中,在0℃氩气保护下,逐滴加入20.71mmol亚硝酸叔丁酯。反应在1小时内逐步回升到室温,TLC追踪反应。反应结束后,加入15mmol的三氟乙酸酐,在室温下搅拌1小时,TLC追踪反应。反应结束后,加入乙酸乙酯/水淬灭反应,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-对三氟甲氧基苄基-4-苯基悉尼酮(收率70%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.68(m,1H),7.56-7.58(m,4H),7.10(m,2H),7.01(m,2H),2.29(s,2H);HRMS(ESI)m/z[M+H]+C16H11N2O3F3,计算值:337.1102,实测值:337.1101.
实施例7:3-三氟甲基苄基-4-三氟甲基苯基悉尼酮的制备
7.1 2-溴-2-(3-三氟甲基苯基)乙酸的制备
将5mmol的NBS,0.2mmol的过氧化二苯甲酰溶解在5ml的四氯化碳中,加热回流该混合物,之后加入溶解在3ml四氯化碳的5mmol的2-三氟甲基苯乙酸。反应加热回流6小时,TLC追踪反应。反应结束后静置冷却,过滤,滤液使用碳酸氢钠溶液洗,分离得到有机相,旋蒸后,通过柱层析得到:2-溴-2-(3-三氟甲基苯基)乙酸(收率70%,淡黄色液体)。1H NMR(400MHz,CDCl3 d)δ:12.75(s,1H),7.45-7.51(m,3H),7.21(m,1H),5.90(s,1H);HRMS(ESI)m/z[M+H]+C9H7BrF3O2,计算值:284.0416,实测值:284.0415.
7.2 2-((4-三氟甲基苄基)氨基)-2-(3-三氟甲基苯基)乙酸的制备
目标化合物的合成与实施例5的步骤5.1类似,不同点在于,用2-溴-2-(3-三氟甲基苯基)乙酸代替α-溴苯乙酸,用4-三氟甲基苄胺代替4-甲氨基吡啶。(收率80%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:12.73(s,1H),7.45-7.51(m,5H),7.21(m,1H),7.15(m,2H),4.90(s,1H),4.80(s,1H),3.80(s,2H);HRMS(ESI)m/z[M+H]+C17H14NF6O2,计算值:378.2916,实测值:378.2954.
7.3 3-三氟甲基苄基-4-三氟甲基苯基悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-((4-三氟甲基苄基)氨基)-2-(3-三氟甲基苯基)乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率59%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:8.09(m,1H),7.78(m,2H),7.65(m,2H),7.53(m,1H),7.22(m,2H)2.25(s,2H);HRMS(ESI)m/z[M+H]+C17H11F6N2O2,计算值:389.2712,实测值:389.2716.
实施例8:3-三氟甲基苄基-4-(3,5-二氯苯基)悉尼酮的制备
8.1 2-溴-2-(3,5-二氯苯基)乙酸的制备
将5mmol的NBS,0.2mmol的过氧化二苯甲酰溶解在5ml的四氯化碳中,加热回流该混合物,之后加入溶解在3ml四氯化碳的5mmol的3,5-二氯苯乙酸。反应加热回流6小时,TLC追踪反应。反应结束后静置冷却,过滤,滤液使用碳酸氢钠溶液洗,分离得到有机相,旋蒸后,通过柱层析得到:2-溴-2-(3,5-二氯苯基)乙酸(收率75%,淡黄色液体)。1H NMR(400MHz,CDCl3 d)δ:12.73(s,1H),7.51(s,1H),7.31(s,2H),5.92(s,1H);HRMS(ESI)m/z[M+H]+C8H6BrCl2O2,计算值:284.8842,实测值:284.8843.
8.2 2-((4-三氟甲基苄基)氨基)-2-(3,5-二氯苯基)乙酸的制备
目标化合物的合成与实施例5的步骤5.1类似,不同点在于,用2-溴-2-(3,5-二氯苯基)乙酸代替α-溴苯乙酸,用4-三氟甲基苄胺代替4-甲氨基吡啶。(收率82%,白色固体)。1HNMR(400MHz,CDCl3 d)δ:12.72(s,1H),7.55-7.58(m,3H),7.34(s,2H),7.20(m,2H),5.00(s,1H),4.82(s,1H).3.80(s,2H);HRMS(ESI)m/z[M+H]+C16H13Cl2NF3O2,计算值:379.1725,实测值:379.1735.
8.3 3-三氟甲基苄基-4-(3,5-二氯苯基)悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-((4-三氟甲基苄基)氨基)-2-(3,5-二氯苯基)乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率63%,淡黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.89(m,2H),7.78(m,1H),7.65(m,2H),7.53(m,2H),2.28(s,2H);HRMS(ESI)m/z[M+H]+C16H10 Cl2F3N2O2,计算值:390.1622,实测值:390.1631.
实施例9:3-噻吩甲基-4-苯基悉尼酮的制备
9.1 2-苯基-2-(2-噻吩基甲基氨基)乙酸的制备
目标化合物的合成与实施例5的步骤5.1类似,不同点在于,用2-氨甲基噻吩代替4-甲氨基吡啶。(收率92%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:12.72(s,1H),7.27-7.31(m,5H),7.44(m,1H),7.10(m,1H),7.00(m,1H),5.00(s,1H),4.82(s,1H).3.80(s,2H);HRMS(ESI)m/z[M+H]+C13H14NSO2,计算值:248.3112,实测值:248.3115.
9.2 3-噻吩甲基-4-苯基悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-苯基-2-(2-噻吩基甲基氨基)乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率63%,淡黄色固体)。1HNMR(400MHz,CDCl3 d)δ:7.69(m,2H),7.56(m,1H),7.51(m,2H),7.33(m,1H),6.95(m,1H),6.82(m,1H),2.30(s,2H);HRMS(ESI)m/z[M+H]+C13H11SN2O2,计算值:259.3012,实测值:259.3022.
实施例10:3-环丙基甲基-4-苯基悉尼酮的制备
10.1 2-苯基-2-(环丙基甲基氨基)乙酸的制备
目标化合物的合成与实施例5的步骤5.1类似,不同点在于,用环丙基甲胺代替4-甲氨基吡啶。(收率81%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:12.72(s,1H),7.27-7.31(m,5H),4.82(s,1H),4.78(s,1H).2.44(s,2H),1.02(m,1H),0.41(m,2H),0.15(m,2H);HRMS(ESI)m/z[M+H]+C12H16NO2,计算值:206.2612,实测值:206.2615.
10.2 3-环丙基甲基-4-苯基悉尼酮的制备
目标化合物的合成与实施例1的步骤1.2类似,不同点在于,用2-苯基-2-(环丙基甲基氨基)乙酸代替2-(2-甲基-4-七氟异丙基苯基)氨基乙酸。(收率50%,淡黄色固体)。1HNMR(400MHz,CDCl3 d)δ:7.69(m,2H),7.56(m,1H),7.51(m,2H),1.03(m,1H),0.92(m,2H),0.40(m,2H),0.16(m,2H);HRMS(ESI)m/z[M+H]+C12H13N2O2,计算值:217.2412,实测值:217.2435.
实施例11:N-Boc-3-庚基悉尼酮亚胺的制备
11.1 2-庚胺基乙腈的制备
将92.29mmol的庚胺与101.79mmol的三乙胺加入到33.8ml乙酸乙酯中,保持反应体系低于5℃。92.54mmol的溴乙腈在2小时内逐滴加入到反应体系中。结束滴加后,反应室温搅拌3小时,TLC追踪反应。反应结束后加入33.8ml的水。分离有机相,使用10%的氯化钠溶液洗,悬除溶剂,柱层析纯化,得到2-(庚胺)乙腈(收率58%,无色液体)。1H NMR(400MHz,CDCl3 d1)δ:3.81(s,2H),3.31(s,1H),2.46(m,2H),1.41(m,2H),1.31-1.36(m,8H),0.92(m,3H);HRMS(ESI)m/z[M+H]+C9H19N2,计算值:155.2642,实测值:155.2641.
11.2 3-庚基悉尼酮亚胺盐酸盐的制备
将5mmol 2-(庚胺)乙腈溶解到5ml乙醚中,加入7.5mmol的亚硝酸叔丁酯,TLC追踪反应。反应结束后,在冰浴条件下,向反应液中通入干燥的氯化氢气体,TLC追踪反应。反应结束后,悉尼酮亚胺盐酸盐会结晶析出,通过过滤,石油醚/乙醚(1:1)洗之后,在异丙醇或乙醇中重结晶得到产物(收率71%,白色固体)。1H NMR(400MHz,D2O)δ:9.95(br.s,2H),7.71(s,1H),1.41(m,2H),1.33-1.38(m,8H),0.92(m,2H),0.82(m,3H);HRMS(ESI)m/z[M+H]+C9H19N3O,计算值:185.2603,实测值:185.2604.
11.3N-Boc-3-庚基悉尼酮亚胺的制备
将25mmol 3-庚基悉尼酮亚胺盐酸盐,75mmol二碳酸二叔丁酯,1.25mmol DMAP,溶解在100ml氯仿中,回流2-3小时,直至反应停止放出气体。冷却至室温后,加入20ml5%的碳酸氢钠溶液,分离后水相用氯仿萃取,合并有机相,使用无水硫酸钠干燥,之后悬干溶剂。产物通过异丙醇/石油醚进行重结晶(收率65%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.72(s,1H),1.48(s,9H),1.43(m,2H),1.32-1.37(m,8H),0.90(m,2H),0.81(m,3H);HRMS(ESI)m/z[M+H]+C14H26N3O3,计算值:284.1903,实测值:284.1904.
实施例12:N(6)-Boc-3-对氟苄基-4-苯基悉尼酮亚胺的制备
12.1α-溴苯乙腈的制备
将5mmol的NBS,0.2mmol的过氧化二苯甲酰溶解在5ml的四氯化碳中,加热回流该混合物,之后加入溶解在3ml四氯化碳的5mmol的苯乙腈。反应加热回流6小时,TLC追踪反应。反应结束后静置冷却,过滤,滤液使用碳酸氢钠溶液洗,分离得到有机相,旋蒸后,通过柱层析得到:α-溴苯乙腈(收率75%,淡黄色液体)。1H NMR(400MHz,CDCl3d)δ:7.25-7.35(m,5H),5.97(s,1H);HRMS(ESI)m/z[M+H]+C8H7BrN,计算值:196.9703,实测值:196.9705.
12.2 2-(4-氟苄基氨基)-2-苯乙腈的制备
将10mmol的对氟苄胺溶解在50ml乙酸乙酯中,加入10mmol的α-溴苯乙腈和10mmol的三乙胺。过夜搅拌反应,TLC追踪反应。反应结束后加水,使用乙酸乙酯萃取,之后使用饱和氯化钠溶液洗,分离得到有机相,旋蒸后,通过柱层析得到:2-(4-氟苄基氨基)-2-苯乙腈(收率70%,黄色液体)。1H NMR(400MHz,CDCl3 d)δ:7.62(m,2H),7.41-7.44(m,5H),7.07(m,2H),5.01(s,1H),4.93(s,1H),3.78(s,2H);HRMS(ESI)m/z[M+H]+C15H14FN2,计算值:241.1101,实测值:241.1102.
12.3 3-对氟苄基-4-苯基悉尼酮亚胺盐酸盐的制备
将5mmol 2-(4-氟苄基氨基)-2-苯乙腈溶解到5ml乙醚中,加入7.5mmol的亚硝酸叔丁酯,TLC追踪反应。反应结束后,在冰浴条件下,向反应液中通入干燥的氯化氢气体,TLC追踪反应。反应结束后,悉尼酮亚胺盐酸盐会结晶析出,通过过滤,石油醚/乙醚(1:1)洗之后,在异丙醇或乙醇中重结晶得到产物(收率71%,白色固体)。1H NMR(400MHz,D2O)δ:9.95(br.s,2H),7.75(m,2H),7.69(m,2H),7.59-7.61(m,3H),7.18(m,2H),2.28(s,2H);HRMS(ESI)m/z[M+H]+C15H14FN3O,计算值:271.0721,实测值:271.0720.
12.4 N(6)-Boc-3-对氟苄基-4-苯基悉尼酮亚胺的制备
将25mmol 3-对氟苄基-4-苯基悉尼酮亚胺盐酸盐,75mmol二碳酸二叔丁酯,1.25mmol DMAP,溶解在100ml氯仿中,回流2-3小时,直至反应停止放出气体。冷却至室温后,加入20ml 5%的碳酸氢钠溶液,分离后水相用氯仿萃取,合并有机相,使用无水硫酸钠干燥,之后悬干溶剂。产物通过异丙醇/石油醚进行重结晶(收率65%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.72(m,2H),7.68(m,2H),7.61(m,2H),7.56(m,1H),7.21(m,2H),2.25(m,2H),1.42(m,9H);HRMS(ESI)m/z[M+H]+C20H21FN3O3,计算值:370.1503,实测值:370.1505.
实施例13:N(6)-苯甲酰基-3-庚基悉尼酮亚胺的制备
将37mmol 3-庚基悉尼酮亚胺盐酸盐加入到溶有44mmol苯甲酰氯的70ml二氯甲烷中,之后加入11.8ml三乙胺,在-20℃中搅拌15分钟。在室温下搅拌16小时,加入50ml水,分离后水相用二氯甲烷萃取,合并有机相,使用无水硫酸钠干燥,之后悬干溶剂。产物通过异丙醇进行重结晶(收率62%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.86(m,2H),7.75(m,1H),7.72(s,1H),7.62(m,2H),1.22-1.27(m,10H),0.90(m,2H),0.81(m,3H);HRMS(ESI)m/z[M+H]+C16H22N3O2,计算值:288.1626,实测值:288.1627.
实施例14:3-庚基-N(6)-对甲基苯磺酰基-悉尼酮亚胺的制备
将92mmol 3-庚基悉尼酮亚胺盐酸盐加入到溶有101mmol对甲基苯磺酰氯的150ml二氯甲烷中,之后将此混合物滴加到含有138mmol三乙胺的50ml二氯甲烷中,之后在-20℃中搅拌15分钟。在室温下搅拌16小时,过滤除去不溶物,溶液使用水和5%的碳酸钾溶液洗涤,使用无水硫酸钠干燥,之后悬干溶剂。产物通过异丙醇/石油醚(1:1.2)进行重结晶(收率72%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.76(m,3H),7.40(m,2H),2.45(m,3H),1.23-1.30(m,10H),0.95(m,2H),0.86(m,3H);HRMS(ESI)m/z[M+H]+C16H24N3O3S,计算值:338.1534,实测值:338.1533.
实施例15:3-庚基-N(6)-三氟乙酰基-悉尼酮亚胺的制备
将62mmol 3-庚基悉尼酮亚胺盐酸盐溶解在200ml二氯甲烷中,在此混合物中滴加10.4ml三氟乙酸酐,在-20℃中搅拌中滴加20.5ml三乙胺,之后搅拌30分钟。在室温下搅拌16小时。加入150ml水,使用碳酸钾中和,分离得到有机相,使用无水硫酸钠干燥,之后悬干溶剂。产物通过异丙醇/石油醚(1:2)进行重结晶(收率82%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.76(s,1H),1.25-1.30(m,10H),0.97(m,2H),0.87(m,3H);HRMS(ESI)m/z[M+H]+C11H17F3N3O2,计算值:280.1203,实测值:280.1204.
实施例16:3-(3,5-二氯苄基)-N(6)-三氟乙酰基-悉尼酮亚胺
16.1 2-(3,5-二氯苯基)氨基乙腈的制备
将10mmol的3,5-二氯苯甲醛将入到溶有20mmol的氢氧化钾和10mmol的氨基乙腈盐酸盐的20ml水溶液中,然后加入20ml乙醇,搅拌一小时。之后加入12mmol的硼氢化钠,室温过夜搅拌。之后加入盐酸,将反应调整至酸性,使用乙酸乙酯萃取,分离得到有机相,使用饱和食盐水洗,分离有机相,使用无水硫酸钠干燥,悬干溶剂得到产物。(收率80%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.58(s,1H),7.31(m,2H),4.16(s,1H),3.77(s,2H),3.66(s,2H);HRMS(ESI)m/z[M+H]+C9H9N2Cl2,计算值:216.0812,实测值:216.0835.
16.2 3,5-二氯苄基悉尼酮亚胺盐酸盐的制备
目标化合物的合成与实施例11的步骤11.2类似,不同点在于,用2-(3,5-二氯苯基)氨基乙腈代替2-庚胺基乙腈。(收率81%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:9.95(br.s,2H),7.78(s,1H),7.58(s,1H),7.31(m,2H),2.22(s,2H);HRMS(ESI)m/z[M+H]+C9H9N3OCl2,计算值:246.0812,实测值:246.0825.
16.3 3-(3,5-二氯苄基)-N(6)-三氟乙酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐。(收率51%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),2.21(s,2H);HRMS(ESI)m/z[M+H]+C11H7N3O2Cl2F3,计算值:341.0822,实测值:341.0832.
实施例17:3-(3,5-二氯苄基)-N(6)-二氯乙酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用二氯乙酰氯代替三氟乙酸酐。(收率50%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),6.33(s,1H),2.21(s,2H);HRMS(ESI)m/z[M+H]+C11H8N3O2Cl4,计算值:356.0013,实测值:356.0012.
实施例18:3-(3,5-二氯苄基)-N(6)-溴乙酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用溴乙酰氯代替三氟乙酸酐。(收率50%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),4.41(s,2H),2.21(s,2H);HRMS(ESI)m/z[M+H]+C11H9N3O2Cl2Br,计算值:366.0123,实测值:366.0122.
实施例19:N(6)-二氟乙酰基-3-对氟苄基-4-苯基悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3-对氟苄基-4-苯基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用二氟乙酰氯代替三氟乙酸酐。(收率50%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(m,2H),7.69(m,2H),7.61(m,2H),7.51(m,1H),7.21(m,2H),6.02(m,1H),2.23(s,2H);HRMS(ESI)m/z[M+H]+C17H13N3O2F3,计算值:348.3053,实测值:348.3056.
实施例20:3-庚基-N(6)-三氯乙酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用三氯乙酰氯代替三氟乙酸酐。(收率51%,黄色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(m,2H),1.26-1.30(m,10H),0.98(m,3H),0.86(m,2H);HRMS(ESI)m/z[M+H]+C11H17N3O2Cl3,计算值:329.6212,实测值:329.6216.
实施例21:3-(3,5-二氯苄基)-N(6)-6-三氟甲基烟酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用6-三氟甲基烟酰氯代替三氟乙酸酐。(收率40%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:8.66(s,1H),8.06(m,1H),7.75(s,1H),7.61(s,1H),7.36(m,1H),7.21(m,2H),2.26(s,2H);HRMS(ESI)m/z[M+H]+C16H10N4O2Cl2F3,计算值:418.0133,实测值:418.0132.
实施例22:3-(3,5-二氯苄基)-N(6)-3-(二氟甲基)-1-甲基-1H-吡唑-4-酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用3-(二氟甲基)-1-甲基-1H-吡唑-4-酰氯代替三氟乙酸酐。(收率48%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:8.70(s,1H),7.75(s,1H),7.61(s,1H),7.21(m,2H),6.45(m,1H),3.82(s,3H),2.26(s,2H);HRMS(ESI)m/z[M+H]+C15H12N5O2Cl2F2,计算值:403.0243,实测值:403.0242.
实施例23:3-(3,5-二氯苄基)-N(6)-磷酰二甲酯-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用磷酰氯二甲酯代替三氟乙酸酐。(收率68%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),3.81(s,6H),2.26(s,2H);HRMS(ESI)m/z[M+H]+C11H13N3O4PCl2,计算值:353.1022,实测值:353.1040.
实施例24:3-(3,5-二氯苄基)-N(6)-4-吗啉乙酰基-悉尼酮亚胺的制备
目标化合物的合成与实施例15类似,不同点在于,用3,5-二氯苄基悉尼酮亚胺盐酸盐代替3-庚基悉尼酮亚胺盐酸盐,用4-吗啉乙酰氯代替三氟乙酸酐。(收率52%,白色固体)。1H NMR(400MHz,CDCl3 d)δ:7.75(s,1H),7.61(s,1H),7.21(m,2H),3.68(m,4H),3.41(s,2H),2.57(m,4H),2.26(s,2H);HRMS(ESI)m/z[M+H]+C15H17N4O3Cl2,计算值:372.2024,实测值:372.2034.
采用与实施例1-24的合成方法,选用不用的原料制备表1中的其他化合物。
实施例25:本发明化合物的活体抗菌活性测试
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。另配制对照药氰霜唑6.25mg/L的药液20ml,嘧菌酯25mg/L的药液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。根据以下公式计算防治效果(抑制率)。
实施例26:本发明化合物的离体抗菌活性测试
取新化合物0.00625mg溶解入1ml中二甲亚砜,配制成6.25mg/L的药液。另配制对照药剂啶菌噁唑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80μL,稻瘟病置于28℃黑暗培养箱中培养18h,灰霉病置于18℃黑暗培养箱中培养18h,之后调查。
离体筛选采用HTS方法。
表1式(I)化合物的抗菌活性
实施例27: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-268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-268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-268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,L为H、卤素(氟、氯、溴、碘)、羟基、硝基、羧基、氰基、SHSF5、SCN、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、-CONRaRb、C6-C10芳基、-C(O)(C6-C10芳基)、-COO(C6-C10芳基)、-COO(C6-C10芳基)(C2-C6烯基)、-COO(C1-C8亚烷基)(C6-C10芳基)、-COO(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)、-C(O)(C1-C8亚烷基)(C6-C10芳基)、-(C1-C8亚烷基)(C3-C6环烷基)、-C(O)(C1-C8烷基)、-C(O)(4-8元杂芳基)、-C(O)(4-8元杂环基)、-C(O)(C3-C6环烷基)、-(C1-C8亚烷基)(4-10元杂环基)、-(C1-C8亚烷基)NHCO(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;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、-CONH(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、-COO(C1-C8烷基)或C1-C6硫代烷基;
Q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、-(C1-C8亚烷基)(C3-C6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)、-COO(C6-C10芳基)、-COO(4-8元杂芳基)、-COO(C1-C10烷基)、-COO(C3-C6环烷基)、-COO(4-8元杂环基)、-C(O)(C6-C10芳基)NHCO(4-10元杂芳基)、-(C6-C10芳基)(C6-C10芳基)NHCO(4-10元杂芳基)、-(C6-C10芳基)NHCO(4-10元杂芳基)、-CONRcRd、-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、-CONH(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;
M为O-或N-R1;其中,R1为取代或未取代的选自下组的基团:-COO(C1-C8烷基)、-SO2(C1-C8烷基)、-C(O)(C1-C8烷基)、-C(O)(C6-C10芳基)、-SO2(C6-C10芳基)、-C(O)(4-8元杂芳基)、-P(O)(OC1-C8烷基)(OC1-C8烷基)、-CO(C1-C8亚烷基)(4-8元杂环基)、-COO(C6-C10芳基)、-COO(4-8元杂芳基)、-COO(C3-C8环烷基)、-COO(4-8元杂环基)、-SO2(C3-C8环烷基)、-SO2(4-8元杂芳基)、-SO2(4-8元杂环基)、-C(O)(C3-C8环烷基)、-C(O)(4-8元杂环基)、-CO(C1-C8亚烷基)(C3-C8环烷基)、-CO(C1-C8亚烷基)(C6-C10芳基)、-CO(C1-C8亚烷基)(4-8元杂芳基)、-CO(C1-C8亚烷基)(C3-C8环烷基)、-SO(C1-C8烷基)、-SO(C6-C10芳基)、-SO(C3-C8环烷基)、-SO(4-8元杂芳基)、-SO(4-8元杂环基)、-CONReRf,其中Re、Rf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;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。
2.如权利要求1所述的化合物,其特征在于,M为O-或N-R1;其中,R1为取代或未取代的选自下组的基团:-COO(C1-C6烷基)、-SO2(C1-C4烷基)、-C(O)(C1-C4烷基)、-C(O)苯基、-SO2苯基、-C(O)(5-6元杂芳基)、-P(O)(OC1-C4烷基)(OC1-C4烷基)、-CO(C1-C4亚烷基)(5-6元杂环基)、-COO苯基、-COO(5-6元杂芳基)、-COO(C3-C6环烷基)、-COO(5-6元杂环基)、-SO2(C3-C6环烷基)、-SO2(5-6元杂芳基)、-SO2(5-6元杂环基)、-C(O)(C3-C6环烷基)、-C(O)(5-6元杂环基)、-CO(C1-C4亚烷基)(C3-C6环烷基)、-CO(C1-C4亚烷基)苯基、-CO(C1-C4亚烷基)(5-6元杂芳基)、-CO(C1-C4亚烷基)(C3-C6环烷基)、-SO(C1-C4烷基)、-SO苯基、-SO(C3-C6环烷基)、-SO(5-6元杂芳基)、-SO(5-6元杂环基)、-CONReRf,其中Re、Rf独立地选自H、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、4-8元杂芳基、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: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、苯基、5-6元杂芳基、5-6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。
3.如权利要求1所述的化合物,其特征在于,L为H、氟、氯、溴、碘、羟基、硝基、羧基、氰基、SHSF5、SCN、或者取代或未取代的选自下组的基团:C1-C4烷基、C2-C4烯基、C3-C6环烷基、C2-C4烯氧基、C2-C4炔基、C2-C4炔氧基、C1-C4烷氧基、C3-C6环烷氧基、C5-C6环烯基、5-6元杂环基、-CONRaRb、苯基、-C(O)苯基、-COO苯基、-COO苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基(C2-C4烯基)、-COO(C1-C4亚烷基)苯基、5-6元杂芳基、-(C1-C4亚烷基)(4-10元杂芳基)、-(C1-C4亚烷基)苯基、-C(O)(C1-C4亚烷基)苯基、-(C1-C4亚烷基)(C3-C6环烷基)、-C(O)(C1-C4烷基)、-C(O)(5-6元杂芳基)、-C(O)(5-6元杂环基)、-C(O)(C3-C6环烷基)、-(C1-C4亚烷基)(5-10元杂环基)、-(C1-C4亚烷基)NHCO(4-10元杂芳基)、-NRaRb;其中Ra、Rb各自独立地选自H、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、5-6元杂芳基、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:氰基、羟基、氧代(=O)、C1-C4烷基、卤素(氟、氯、溴)、C1-C4卤代烷基、-CONH(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、C2-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-COO(C1-C4烷基)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,Q为取代或未取代的选自下组的基团:C2-C10烷基、C2-C5烯基、C2-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-(C1-C4亚烷基)(C3-C6环烷基)、-(C1-C4亚烷基)(苯基)、-(C1-C4亚烷基)(5-6元杂芳基)、-(C1-C4亚烷基)(5-6元杂环基)、-C(O)(苯基)、-C(O)(5-6元杂芳基)、-C(O)(C1-C4烷基)、-C(O)(C3-C6环烷基)、-C(O)(5-6元杂环基)、-COO(苯基)、-COO(5-6元杂芳基)、-COO(C1-C4烷基)、-COO(C3-C6环烷基)、-COO(5-6元杂环基)、-C(O)(苯基)NHCO(4-6元杂芳基)、-(苯基)(苯基)NHCO(4-6元杂芳基)、-(苯基)NHCO(4-6元杂芳基)、-CONRcRd、-NRcRd;其中Rc、Rd各自独立地选自:氢、C1-C4烷基、C3-C6环烷基、C1-C4卤代烷基、苯基、4-8元杂芳基、4-8元杂环基、-C(O)(苯基)、-C(O)(4-6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-C4烷基、氟、氯、溴、C1-C4卤代烷基、卤代4-6元杂芳基、-CONH(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-C4炔基、苯基、5-6元杂芳基、5-6元杂环基、-O(苯基)或C1-C4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中任一项所述的化合物,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,用于防治植物病害或制备杀菌剂。
9.如权利要求1所述的用途,其特征在于,所述杀菌剂防治以下病害:炭疽病、霜霉病、白锈菌、猝倒病、绵腐病、疫病、晚疫病、根腐病、立枯病、黄萎病、黑星病、灰霉病、褐斑病、黑斑病、斑枯病、早疫病、轮纹病、叶枯病、茎基腐病、锈病、黑穗病、纹枯病、白粉病、菌核病、黑星病、根肿病。
10.一种防治植物真菌病害的方法,其特征在于,包括给植物施用权利要求1-5中任一项所述的化合物,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步骤。
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