CN107778298B - 含嘧啶的取代唑类化合物及其用途 - Google Patents
含嘧啶的取代唑类化合物及其用途 Download PDFInfo
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- CN107778298B CN107778298B CN201610720596.1A CN201610720596A CN107778298B CN 107778298 B CN107778298 B CN 107778298B CN 201610720596 A CN201610720596 A CN 201610720596A CN 107778298 B CN107778298 B CN 107778298B
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
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- CKTMNVYYEURBPC-UHFFFAOYSA-N bromic acid;2-bromoethanamine Chemical compound NCCBr.OBr(=O)=O CKTMNVYYEURBPC-UHFFFAOYSA-N 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
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- 239000013043 chemical agent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 229940099686 dirofilaria immitis Drugs 0.000 description 1
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- 239000002552 dosage form Substances 0.000 description 1
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- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000004994 halo alkoxy alkyl group Chemical group 0.000 description 1
- 125000005280 halo alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000000262 haloalkenyl group Chemical group 0.000 description 1
- 125000005291 haloalkenyloxy group Chemical group 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000006797 haloalkoxycarbonyloxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004992 haloalkylamino group Chemical group 0.000 description 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 description 1
- 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 description 1
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
- 125000004995 haloalkylthio group Chemical group 0.000 description 1
- 125000000232 haloalkynyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 210000001624 hip Anatomy 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229930189914 platycodon Natural products 0.000 description 1
- 150000004291 polyenes Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 210000000623 ulna Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/74—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
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—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 three or more hetero rings
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Abstract
本发明公开了一种含嘧啶的取代唑类化合物,结构如通式I所示:
Description
技术领域
本发明属农用杀菌杀虫杀螨剂领域,具体涉及一种含嘧啶的取代唑类化合物及其用途。
背景技术
WO 2003049739报道了如下含嘧啶的取代唑类化合物可以抑制蛋白激酶活性,从而对相关蛋白激酶引起的疾病具有治疗作用,如糖尿病、肿瘤、中风等。
WO 2015187089和WO 2014084778均报道了如下含嘧啶的取代噻二唑类化合物,分别对自身免疫性疾病具有治疗作用、抗炎作用和抗肿瘤作用。
现有技术中,结构如本发明通式I所示的化合物未见报道。
发明内容
本发明的目的在于提供一种可以控制多种病菌、害虫害螨的含嘧啶的取代唑类化合物,它可用于农业或其他领域中制备防治病菌和/或害虫害螨的药物。
本发明的技术方案如下:
一种含嘧啶的取代唑类化合物,其特征在于:化合物如通式I所示:
R1选自氢、卤素、氰基、硝基、氨基、羧基、C1-C12烷基、卤代C1-C12烷基、C3-C12环烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C1-C12烷硫基、卤代C1-C12烷硫基、C1-C12烷基亚磺酰基、C1-C12烷基磺酰基、C2-C12烯基、卤代C2-C12烯基、C2-C12炔基、卤代C2-C12炔基、C3-C12烯氧基、卤代C3-C12烯氧基、C3-C12炔氧基、卤代C3-C12炔氧基、C1-C12烷基氨基、二(C1-C12烷基)氨基、C1-C12烷基氨基羰基、卤代C1-C12烷基氨基羰基、C1-C12烷氧基羰基、卤代C1-C12烷氧基羰基、C1-C12烷氧基C1-C12烷基或C1-C2烷硫基C1-C12烷基;
R2选自氢、卤素、氰基、硝基、氨基、羧基、甲酰基、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷氧基;
R1和R2与相连的嘧啶环组成含C、N、O或S的五元、六元、七元或八元环;
X选自NR3、O或S;
Y选自NR3、O或S;
R3选自氢、羟基、甲酰基、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C3-C12环烷基、C1-C12烷硫基、C2-C12烯基硫基、C2-C12烯基、C2-C12炔基、卤代C2-C12烯基、卤代C2-C12炔基、C1-C12烷氧基C1-C12烷基、卤代C1-C12烷氧基C1-C12烷基、C1-C12烷硫基C1-C12烷基、卤代C1-C12烷硫基C1-C12烷基、C1-C12烷基亚磺酰基、卤代C1-C12烷基亚磺酰基、C1-C12烷基磺酰基、卤代C1-C12烷基磺酰基、C1-C12烷基氨基磺酰基、二(C1-C12烷基)氨基磺酰基、C1-C12烷基磺酰基氨基羰基、C1-C12烷基羰基氨基磺酰基、C3-C12环烷基氧基羰基、C1-C12烷基羰基、卤代C1-C12烷基羰基、C1-C12烷氧基羰基、卤代C1-C12烷氧基羰基、C1-C12烷基羰基C1-C12烷基、C1-C12烷氧基羰基C1-C12烷基、C1-C12烷基氨基羰基、二(C1-C12烷基)氨基羰基、C2-C12烯氧基羰基、C2-C12炔氧基羰基、C1-C12烷氧基C1-C12烷氧基羰基、C1-C12烷基氨基硫基、二(C1-C12烷基)氨基硫基、未取代的或被1-5个下述基团(A)取代的基团(B),其中,基团(B)为芳基羰基C1-C6烷基、芳基羰基、芳氧基羰基、芳基C1-C6烷基氧基羰基、芳基C1-C6烷基、杂芳基羰基C1-C6烷基、杂芳基羰基、杂芳氧基羰基、杂芳基C1-C6烷基氧基羰基或杂芳基C1-C6烷基,下述基团(A)为卤素、硝基、氰基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;
R4、R5为相同或不同,分别选自氢、卤素、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷氧基;或,R4、R5与其相连的C组成C3-C8的环;
R6、R7为相同或不同,分别选自氢、卤素、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷氧基;或,R6、R7与其相连的C组成C3-C8的环;
m选自0至5的整数;
Het选自未取代的或被R8或R9取代的含有三个杂原子的五元环;其中,三个杂原子可相同或不同的选自N、S或O;
R8选自氢、氰基、卤素、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基羰基、卤代C1-C12烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R9选自C1-C12烷基、C3-C8环烷基、卤代C1-C12烷基、C1-C12烷基羰基、卤代C1-C12烷基羰基、C1-C12烷基磺酰基、卤代C1-C12烷基磺酰基、C1-C12烷氧基羰基、C1-C12烷氧基C1-C12烷基、C1-C12烷氧基羰基C1-C12烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R10选自卤素、羟基、氨基、氰基、硝基、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基、卤代C1-C12烷氧基、C3-C12环烷基、C1-C12烷基氨基、卤代C1-C12烷基氨基、二(C1-C12烷基)氨基、卤代二(C1-C12烷基)氨基、C(=O)NR11R12、C1-C12烷硫基、卤代C1-C12烷硫基、C2-C12烯基、C2-C12炔基、C2-C12烯氧基、卤代C2-C12烯氧基、C2-C12炔氧基、卤代C2-C12炔氧基、C1-C12烷基磺酰基、卤代C1-C12烷基磺酰基、C1-C12烷基羰基、卤代C1-C12烷基羰基、C1-C12烷氧基羰基、卤代C1-C12烷氧基羰基、C1-C12烷氧基C1-C12烷基、卤代C1-C12烷氧基C1-C12烷基、C1-C12烷硫基C1-C12烷基、卤代C1-C12烷硫基C1-C12烷基、C1-C12烷氧基羰基C1-C12烷基、卤代C1-C12烷氧基羰基C1-C12烷基、C1-C12烷硫基羰基C1-C12烷基、卤代C1-C12烷硫基羰基C1-C12烷基、C1-C12烷基羰基氧基、卤代C1-C12烷基羰基氧基、C1-C12烷氧基羰基氧基、卤代C1-C12烷氧基羰基氧基、C1-C12烷基磺酰基氧基、卤代C1-C12烷基磺酰基氧基、C1-C12烷氧基C1-C12烷氧基或卤代C1-C12烷氧基C1-C12烷氧基;
R11、R12为相同或不同,分别选自氢、C1-C12烷基或卤代C1-C12烷基;
W选自氢、卤素、C1-C12烷基、卤代C1-C12烷基、C3-C8环烷基、C1-C12烷氧基、C1-C12烷硫基或C1-C12烷基磺酰基;
或通式I所示化合物的盐。
优选,通式I所示含嘧啶的取代唑类化合物,式中,
R1选自氢、卤素、氰基、硝基、氨基、羧基、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷硫基、C2-C6烯基、卤代C2-C6烯基、C2-C6炔基、卤代C2-C6炔基、C3-C6烯氧基、卤代C3-C6烯氧基、C3-C6炔氧基、卤代C3-C6炔氧基、C1-C6烷基氨基、二(C1-C6烷基)氨基、C1-C6烷基氨基羰基、卤代C1-C6烷基氨基羰基、C1-C6烷氧基羰基、卤代C1-C6烷氧基羰基、C1-C6烷氧基C1-C6烷基或C1-C6烷硫基C1-C6烷基;
R2选自氢、卤素、氰基、硝基、氨基、羧基、甲酰基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;
R1和R2与相连的嘧啶环组成含C、N、O或S的五元或六元环;
X选自NR3、O或S;
Y选自NR3、O或S;
R3选自氢、羟基、甲酰基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C3-C6环烷基、C1-C6烷硫基、C2-C6烯基硫基、C2-C6烯基、C2-C6炔基、卤代C2-C6烯基、卤代C2-C6炔基、C1-C6烷氧基C1-C6烷基、卤代C1-C6烷氧基C1-C6烷基、C1-C6烷硫基C1-C6烷基、卤代C1-C6烷硫基C1-C6烷基、C1-C6烷基亚磺酰基、卤代C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6烷基)氨基磺酰基、C1-C6烷基磺酰基氨基羰基、C1-C6烷基羰基氨基磺酰基、C3-C6环烷基氧基羰基、C1-C6烷基羰基、卤代C1-C6烷基羰基、C1-C6烷氧基羰基、卤代C1-C6烷氧基羰基、C1-C6烷基羰基C1-C6烷基、C1-C6烷氧基羰基C1-C6烷基、C1-C6烷基氨基羰基、二(C1-C6烷基)氨基羰基、C2-C6烯氧基羰基、C2-C6炔氧基羰基、C1-C6烷氧基C1-C6烷氧基羰基、C1-C6烷基氨基硫基、二(C1-C6烷基)氨基硫基、未取代的或被1-5个下述基团(A)取代的基团(B),其中,基团(B)为芳基羰基C1-C6烷基、芳基羰基、芳氧基羰基、芳基C1-C6烷基氧基羰基、芳基C1-C6烷基、杂芳基羰基C1-C6烷基、杂芳基羰基、杂芳氧基羰基、杂芳基C1-C6烷基氧基羰基或杂芳基C1-C6烷基,下述基团(A)为卤素、硝基、氰基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;
R4、R5为相同或不同,分别选自氢、卤素、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;或,R4、R5与其相连的C组成C3-C6的环;
R6、R7为相同或不同,分别选自氢、卤素、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基或卤代C1-C6烷氧基;或,R6、R7与其相连的C组成C3-C6的环;
m选自0至4的整数;
Het选自未取代的或被R8或R9取代的含有三个杂原子的五元环;
R8选自氢、氰基、卤素、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基羰基、卤代C1-C6烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R9选自C1-C6烷基、C3-C6环烷基、卤代C1-C6烷基、C1-C6烷基羰基、卤代C1-C6烷基羰基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷氧基羰基、C1-C6烷氧基C1-C6烷基、C1-C6烷氧基羰基C1-C6烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R10选自卤素、羟基、氨基、氰基、硝基、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C3-C6环烷基、C1-C6烷基氨基、卤代C1-C6烷基氨基、二(C1-C6烷基)氨基、卤代二(C1-C6烷基)氨基、C(=O)NR11R12、C1-C6烷硫基、卤代C1-C6烷硫基、C2-C6烯基、C2-C6炔基、C2-C6烯氧基、卤代C2-C6烯氧基、C2-C6炔氧基、卤代C2-C6炔氧基、C1-C6烷基磺酰基、卤代C1-C6烷基磺酰基、C1-C6烷基羰基、卤代C1-C6烷基羰基、C1-C6烷氧基羰基、卤代C1-C6烷氧基羰基、C1-C6烷氧基C1-C6烷基、卤代C1-C6烷氧基C1-C6烷基、C1-C6烷硫基C1-C6烷基、卤代C1-C6烷硫基C1-C6烷基、C1-C6烷氧基羰基C1-C6烷基、卤代C1-C6烷氧基羰基C1-C6烷基、C1-C6烷硫基羰基C1-C6烷基、卤代C1-C6烷硫基羰基C1-C6烷基、C1-C6烷基羰基氧基、卤代C1-C6烷基羰基氧基、C1-C6烷氧基羰基氧基、卤代C1-C6烷氧基羰基氧基、C1-C6烷基磺酰基氧基、卤代C1-C6烷基磺酰基氧基、C1-C6烷氧基C1-C6烷氧基或卤代C1-C6烷氧基C1-C6烷氧基;
R11、R12为相同或不同,分别选自氢、C1-C6烷基或卤代C1-C6烷基;
W选自氢、卤素、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基;
或通式I所示化合物的盐。
进一步优选,通式I所示含嘧啶的取代唑类化合物,式中,
R1选自氢、卤素、氰基、硝基、氨基、羧基、C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤代C1-C4烷硫基、C2-C4烯基、卤代C2-C4烯基、C2-C4炔基、卤代C2-C4炔基、C3-C4烯氧基、卤代C3-C4烯氧基、C3-C4炔氧基、卤代C3-C4炔氧基、C1-C4烷基氨基、二(C1-C4烷基)氨基、C1-C4烷基氨基羰基、卤代C1-C4烷基氨基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基或C1-C4烷硫基C1-C4烷基;
R2选自氢、卤素、氰基、硝基、氨基、羧基、甲酰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R1和R2与相连的嘧啶环组成含C、N、O或S的五元或六元环;
X选自NR3、O或S;
Y选自O;
R3选自氢、羟基、甲酰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C4环烷基、C1-C4烷硫基、C2-C4烯基硫基、C2-C4烯基、C2-C4炔基、卤代C2-C4烯基、卤代C2-C4炔基、C1-C4烷氧基C1-C4烷基、卤代C1-C4烷氧基C1-C4烷基、C1-C4烷硫基C1-C4烷基、卤代C1-C4烷硫基C1-C4烷基、C1-C4烷基亚磺酰基、卤代C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基氨基磺酰基、二(C1-C4烷基)氨基磺酰基、C1-C4烷基磺酰基氨基羰基、C1-C4烷基羰基氨基磺酰基、C3-C4环烷基氧基羰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷基羰基C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、C1-C4烷基氨基羰基、二(C1-C4烷基)氨基羰基、C2-C4烯氧基羰基、C2-C4炔氧基羰基、C1-C4烷氧基C1-C4烷氧基羰基、C1-C4烷基氨基硫基、二(C1-C4烷基)氨基硫基、未取代的或被1-5个下述基团(A)取代的基团(B),其中,基团(B)为芳基羰基C1-C4烷基、芳基羰基、芳氧基羰基、芳基C1-C4烷基氧基羰基、芳基C1-C4烷基、杂芳基羰基C1-C4烷基、杂芳基羰基、杂芳氧基羰基、杂芳基C1-C4烷基氧基羰基或杂芳基C1-C4烷基,下述基团(A)为卤素、硝基、氰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R4、R5为相同或不同,分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;或,R4、R5与其相连的C组成C3-C4的环;
R6、R7为相同或不同,分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;或,R6、R7与其相连的C组成C3-C4的环;
m选自0至3的整数;
Het选自未取代的或被R8或R9取代的1,2,4-三唑基、1,2,3-三唑基、1,2,4-噻二唑基、1,2,3-噻二唑基、1,3,4-噻二唑基或1,3,4-恶二唑基;
R8选自氢、氰基、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R9选自C1-C4烷基、C3-C4环烷基、卤代C1-C4烷基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R10选自卤素、羟基、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C4环烷基、C1-C4烷基氨基、卤代C1-C4烷基氨基、二(C1-C4烷基)氨基、卤代二(C1-C4烷基)氨基、C(=O)NR11R12、C1-C4烷硫基、卤代C1-C4烷硫基、C2-C4烯基、C2-C4炔基、C2-C4烯氧基、卤代C2-C4烯氧基、C2-C4炔氧基、卤代C2-C4炔氧基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基、卤代C1-C4烷氧基C1-C4烷基、C1-C4烷硫基C1-C4烷基、卤代C1-C4烷硫基C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、卤代C1-C4烷氧基羰基C1-C4烷基、C1-C4烷硫基羰基C1-C4烷基、卤代C1-C4烷硫基羰基C1-C4烷基、C1-C4烷基羰基氧基、卤代C1-C4烷基羰基氧基、C1-C4烷氧基羰基氧基、卤代C1-C4烷氧基羰基氧基、C1-C4烷基磺酰基氧基、卤代C1-C4烷基磺酰基氧基、C1-C4烷氧基C1-C4烷氧基或卤代C1-C4烷氧基C1-C4烷氧基;
R11、R12为相同或不同,分别选自氢、C1-C4烷基或卤代C1-C4烷基;
W选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C4烷基磺酰基;
或通式I所示化合物的盐。
再进一步优选,通式I结构中如通式I结构如IA、IB、IC、ID、IE、IF、IG、IH、II、IJ、IK、IL、IM、IN、IO、IP、IQ或IR所示,
式中:
R1选自氢、卤素、氰基、硝基、氨基、羧基、C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C2-C4烯基、卤代C2-C4烯基、C2-C4炔基、卤代C2-C4炔基、C3-C4烯氧基、卤代C3-C4烯氧基、C3-C4炔氧基、卤代C3-C4炔氧基、C1-C4烷基氨基、二(C1-C4烷基)氨基、C1-C4烷基氨基羰基、卤代C1-C4烷基氨基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基或C1-C4烷硫基C1-C4烷基;
R2选自氢、卤素、氰基、硝基、氨基、羧基、甲酰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R3选自氢、羟基、甲酰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C4环烷基、C1-C4烷硫基、C2-C4烯基硫基、C2-C4烯基、C2-C4炔基、卤代C2-C4烯基、卤代C2-C4炔基、C1-C4烷氧基C1-C4烷基、卤代C1-C4烷氧基C1-C4烷基、C1-C4烷硫基C1-C4烷基、卤代C1-C4烷硫基C1-C4烷基、C1-C4烷基亚磺酰基、卤代C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基氨基磺酰基、二(C1-C4烷基)氨基磺酰基、C1-C4烷基磺酰基氨基羰基、C1-C4烷基羰基氨基磺酰基、C3-C4环烷基氧基羰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷基羰基C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、C1-C4烷基氨基羰基、二(C1-C4烷基)氨基羰基、C2-C4烯氧基羰基、C2-C4炔氧基羰基、C1-C4烷氧基C1-C4烷氧基羰基、C1-C4烷基氨基硫基、二(C1-C4烷基)氨基硫基、未取代的或被1-5个下述基团(A)取代的基团(B),其中,基团(B)为芳基羰基C1-C4烷基、芳基羰基、芳氧基羰基、芳基C1-C4烷基氧基羰基、芳基C1-C4烷基、杂芳基羰基C1-C4烷基、杂芳基羰基、杂芳氧基羰基、杂芳基C1-C4烷基氧基羰基、杂芳基C1-C4烷基,下述基团(A)为卤素、硝基、氰基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R4、R5为相同或不同,分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;或,R4、R5与其相连的C组成C3-C4的环;
R6、R7为相同或不同,分别选氢、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;或,R6、R7与其相连的C组成C3-C4的环;
m选自1至2的整数;
R8选自氢、氰基、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R10选自卤素、羟基、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C3-C4环烷基、C1-C4烷基氨基、卤代C1-C4烷基氨基、二(C1-C4烷基)氨基、卤代二(C1-C4烷基)氨基、C(=O)NR11R12、C1-C4烷硫基、卤代C1-C4烷硫基、C2-C4烯基、C2-C4炔基、C2-C4烯氧基、卤代C2-C4烯氧基、C2-C4炔氧基、卤代C2-C4炔氧基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基、卤代C1-C4烷氧基C1-C4烷基、C1-C4烷硫基C1-C4烷基、卤代C1-C4烷硫基C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、卤代C1-C4烷氧基羰基C1-C4烷基、C1-C4烷硫基羰基C1-C4烷基、卤代C1-C4烷硫基羰基C1-C4烷基、C1-C4烷基羰基氧基、卤代C1-C4烷基羰基氧基、C1-C4烷氧基羰基氧基、卤代C1-C4烷氧基羰基氧基、C1-C4烷基磺酰基氧基、卤代C1-C4烷基磺酰基氧基、C1-C4烷氧基C1-C4烷氧基或卤代C1-C4烷氧基C1-C4烷氧基;
n选自0至5的整数,当n为0时,苯环上无取代基;当n大于1时,R10为相同或不同;
R11、R12为相同或不同,分别选自氢、C1-C4烷基或卤代C1-C4烷基;
R13选自C1-C4烷基、C3-C4环烷基、卤代C1-C4烷基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷氧基羰基、C1-C4烷氧基C1-C4烷基或C1-C4烷氧基羰基C1-C4烷基;
R14、R15为相同或不同,分别选自氢、卤素、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C3-C4环烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R16、R17、R18、R19为相同或不同,分别选自氢、卤素、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基或卤代C1-C4烷氧基;
R20、R21为相同或不同,分别选自氢、卤素、羟基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C3-C4环烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R22、R23、R24、R25为相同或不同,分别选自氢、卤素、羟基、氨基、氰基、硝基、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基或C3-C4环烷基;
R26、R27为相同或不同,分别选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、卤代C1-C4烷氧基、C1-C4烷硫基、卤代C1-C4烷硫基、C3-C4环烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R28选自C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R29选自氢、氰基、卤素、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R30选自C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷基磺酰基、卤代C1-C4烷基磺酰基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R31选自氢、氰基、卤素、C1-C4烷基、卤代C1-C4烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R32、R33为分别独立的选自C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷基羰基、卤代C1-C4烷基羰基、C1-C4烷氧基羰基、卤代C1-C4烷氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R34、R35为分别独立的选自氢、氰基、卤素、C1-C4烷基、卤代C1-C4烷基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
W选自氢、卤素、C1-C4烷基、卤代C1-C4烷基、C3-C4环烷基、C1-C4烷氧基、C1-C4烷硫基或C1-C4烷基磺酰基;
Het1选自被R8或R9取代的或非取代的1,2,3-三唑、1,2,4-噻二唑、1,2,3-噻二唑基、1,3,4-噻二唑或1,3,4-恶二唑;
或通式IA、IB、IC、ID、IE、IF、IG、IH、II、IJ、IK、IL、IM、IN、IO、IP、IQ或IR所示的化合物与盐酸、硫酸、磷酸、甲酸、乙酸、三氟乙酸、草酸、甲磺酸、对甲苯磺酸、苯甲酸、邻苯二甲酸、马来酸、富马酸、山梨酸、苹果酸或柠檬酸形成的盐。
更进一步优选,通式IA、IB、IC、ID、IE、IF、IG、IH、II、IJ、IK、IL、IM、IN、IO、IP和IQ所示的化合物,式中
R1选自氢、氟、氯、溴、碘、氰基、硝基、氨基、羧基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、一氟甲基、一氯甲基、二氟甲基、三氟甲基、三氟乙基、甲氧基甲基、乙氧基甲基或三氟乙氧基甲基;
R2选自氢、氟、氯、溴、碘、氰基、硝基、氨基、羧基、甲酰基、甲基、乙基、甲氧基、乙氧基或三氟乙氧基;
R3选自氢、羟基、甲酰基、乙酰基、丙酰基、丁酰基、三氟乙酰基、苯甲酰基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氟乙基、甲氧基、乙氧基、三氟乙氧基、环丙基氧基、甲硫基、乙硫基、烯丙基、炔丙基、甲磺酰基、乙磺酰基、三氟乙基磺酰基、甲氨基磺酰基、乙氨基磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、甲磺酰基氨基羰基、甲氧基羰基、乙氧基羰基、丙氧基羰基、异丙氧基羰基、甲氨基羰基、二甲氨基羰基、乙烯氧基羰基、乙炔氧基羰基、甲氨基硫基、乙氨基硫基或二甲氨基硫基;
R4、R5为相同或不同,分别选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基或叔丁氧基;
R6、R7为相同或不同,分别选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基或叔丁氧基;
R8选自氢、氰基、氟、氯、溴、碘、甲基、乙基或三氟甲基;
R10选自氟、氯、溴、碘、氰基、氨基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、甲氧基羰基、乙氧基羰基、氨基羰基、甲基氨基羰基、乙基氨基羰基或二甲氨基羰基;
n选自0至5的整数,当n为0时,苯环上无取代基;当n大于1时,R10为相同或不同;
R13选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、环丙基、环丁基、一氟甲基、一氯甲基、二氟甲基、三氟甲基或三氟乙基;
R14、R15为相同或不同,分别选自氢、氟、氯、溴、碘、氨基、氰基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R16、R17、R18、R19为相同或不同,分别选自氢、氟、氯、溴、碘、氰基、硝基、甲基、三氟甲基、甲氧基或三氟甲氧基;
R20、R21为相同或不同,分别选自氢、氟、氯、溴、碘、羟基、氰基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R22、R23、R24、R25为相同或不同,分别选自氢、氟、氯、溴、碘、氨基、氰基、硝基、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲氧基或三氟乙氧基;
R26、R27为相同或不同,分别选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、三氟乙基、甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、三氟甲氧基、三氟乙氧基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R28选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、环丙基、甲基磺酰基、乙基磺酰基、甲基羰基、乙基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R29选自氢、氰基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R30选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、环丙基、甲基磺酰基、乙基磺酰基、甲基羰基、乙基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R31选自氢、氰基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R32、R33为分别独立的选自甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、环丙基、甲基羰基、乙基羰基、甲氧基羰基、乙氧基羰基、三氟乙氧基羰基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
R34、R35为分别独立的选自氢、氰基、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、三氟甲基、三氯甲基、二氟一氯甲基、二氯一氟甲基、未取代的或被1-5个R10取代的基团(C),其中,基团(C)为芳基、芳甲基、芳基羰基、芳甲基羰基、芳氧基羰基、杂芳基、杂芳甲基、杂芳基羰基、杂芳甲基羰基或杂芳氧基羰基;
W选自氢、氟、氯、溴、碘、甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、一氟甲基、一氯甲基、二氟甲基、三氟甲基、三氟乙基、甲氧基、乙氧基、甲硫基、乙硫基、甲基磺酰基或乙基磺酰基;
或通式IA、IB、IC、ID、IE、IF、IG、IH、II、IJ、IK、IL、IM、IN、IO、IP或IQ化合物与盐酸、硫酸、磷酸、甲酸、乙酸、三氟乙酸、草酸、甲磺酸、对甲苯磺酸、苯甲酸、邻苯二甲酸、马来酸、富马酸、山梨酸、苹果酸或柠檬酸形成的盐。
更再进一步优选,通式IC、IF、IG、IO、IP和IQ化合物,式中
R1选自氢、氟、氯、溴、碘、甲基、乙基或二氟甲基;
R2选自氢、氟、氯、溴、碘、硝基、氨基、甲酰基、甲基、乙基、甲氧基或乙氧基;
R3选自氢、甲基、乙酰基、三氟乙酰基、甲氧基、甲硫基、烯丙基、甲磺酰基、甲氨基磺酰基、二甲氨基磺酰基、甲氧基羰基、甲氨基羰基、二甲氨基羰基、甲氨基硫基或二甲氨基硫基;
R4、R5为相同或不同,分别选自氢、氟、氯、溴或甲基;
R6、R7均选自氢;
R8选自氢;
R10选自氟、氯、溴、碘、氰基、硝基、甲基、三氟甲基、甲氧基或三氟甲氧基;
n选自0至5的整数,当n为0时,苯环上无取代基;当n大于1时,R10为相同或不同;
R22、R23、R24、R25为相同或不同,分别选自氢、氟、氯、溴、碘或甲基;
R26、R27为相同或不同,分别选自氢、氟、氯、溴或碘;
W选自氢、氟、氯、溴、碘或甲基;
或通式IC、IF、IG、IO、IP或IQ化合物与盐酸、硫酸、磷酸、甲酸、乙酸、三氟乙酸、草酸、甲磺酸、对甲苯磺酸、苯甲酸、邻苯二甲酸、马来酸、富马酸、山梨酸、苹果酸或柠檬酸形成的盐。
又一步优选地,通式IC、IF、IG、IO、IP和IQ化合物,式中
R1选自氢、氯、甲基、乙基或二氟甲基;
R2选自氢、氟、氯、溴、硝基、氨基、甲基或甲氧基;
R3选自氢、甲基或甲氨基羰基;
R4、R5为相同或不同,分别选自氢或甲基;
R6、R7均选自氢;
R8选自氢;
R10选自氟、氯、溴、碘、氰基、硝基、甲基、三氟甲基、甲氧基或三氟甲氧基;
n选自0至3的整数,当n为0时,苯环上无取代基;当n大于1时,R10为相同或不同;
R22、R23、R24、R25为相同或不同,分别选自氢或溴;
R26选自氢;
R27选自氯;
W选自氢、氟、氯、溴、碘或甲基;
或通式IC、IF、IG、IO、IP或IQ化合物与盐酸、硫酸、磷酸、甲酸、乙酸、三氟乙酸、草酸、甲磺酸、对甲苯磺酸、苯甲酸、邻苯二甲酸、马来酸、富马酸、山梨酸、苹果酸或柠檬酸形成的盐。
一种所述含嘧啶的取代唑类化合物在农业或其他领域中用作制备杀菌剂、杀虫杀螨剂药物的用途。
一种杀菌杀虫杀螨组合物,组合物以含嘧啶的取代唑类化合物作为活性组分,组合物中活性组分的重量百分含量为0.1-99%。
一种组合物在农业或其他领域中防治病菌、害虫害螨的用途。
上面给出的通式I化合物的定义中,汇集所用术语一般定义如下:
卤素:指氟、氯、溴或碘。
烷基:直链或支链烷基,例如甲基、乙基、丙基、异丙基、正丁基或叔丁基。
环烷基:取代或未取代的环状烷基,例如环丙基、环戊基或环己基。取代基如甲基、卤素等。
卤代烷基:直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤原子所取代,例如,氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。
烷基亚磺酰基:直链或支链烷基经亚磺酰基(-SO-)连接到结构上,如甲基亚磺酰基。
卤代烷基亚磺酰基:直链或支链烷基亚磺酰基,其烷基上的氢原子可部分或全部被卤原子所取代。
卤代烷基磺酰基:直链或支链烷基磺酰基,其烷基上的氢原子可部分或全部被卤原子所取代。
烷基氨基硫基:如CH3NHS-、C2H5NHS-。
二烷基氨基硫基:如(CH3)2NS-、(C2H5)2NS-。
烷基氨基磺酰基:烷基-NH-SO2-。
二烷基氨基磺酰基:(烷基)2-N-SO2-。
烷基磺酰基氨基羰基:烷基-SO2-NH-CO-。
烷基羰基氨基磺酰基:烷基-CO-NH-SO2-。
烷基羰基烷基:烷基-CO-烷基-。
烷基磺酰基氧基:烷基-S(O)2-O-。
卤代烷基磺酰基氧基:烷基磺酰基氧基的烷基上的氢原子可部分或全部被卤原子所取代,例如CF3-SO2-O。
环烷基氧基羰基:如环丙氧基羰基、环己氧基羰基等。
烷氧基:直链或支链烷基,经氧原子键连接到结构上。
卤代烷氧基:直链或支链烷氧基,在这些烷氧基上的氢原子可部分或全部被卤原子所取代。例如,氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。
卤代烷氧基羰基:烷氧基羰基的烷基上的氢原子可部分或全部被卤原子所取代,如ClCH2CH2OCO-、CF3CH2OCO-等。
烷氧基烷基:烷基-O-烷基-,例如CH3OCH2-。
卤代烷氧基烷基:烷氧基烷基的烷基上的氢原子可部分或全部被卤原子所取代,如ClCH2CH2OCH2-、CF3CH2OCH2-等。
烷氧基羰基烷基:烷氧基羰基-烷基-,例如CH3OCOCH2-。
卤代烷氧基羰基烷基:烷氧基羰基烷基的烷基上的氢原子可部分或全部被卤原子所取代,例如CF3CH2OCOCH2-。
烷基羰基氧基:如CH3COO-等。
卤代烷基羰基氧基:烷基羰基氧基的氢原子可部分或全部被卤原子所取代,如CF3COO-等。
烷氧基羰基氧基:烷氧基羰基-氧基-,例如CH3OCOO-。
卤代烷氧基羰基氧基:烷氧基羰基氧基的烷基上的氢原子可部分或全部被卤原子所取代,例如CF3OCOO-。
烷硫基羰基烷基:烷硫基羰基-烷基-,例如CH3SCOCH2-。
卤代烷硫基羰基烷基:烷硫基羰基烷基的烷基上的氢原子可部分或全部被卤原子所取代,例如CF3CH2SCOCH2-。
烷氧基烷氧基:如CH3OCH2O-等。
卤代烷氧基烷氧基:烷氧基上的氢原子可部分或全部被卤原子所取代,例如CF3OCH2O-。
烷氧基烷氧基羰基:如CH3OCH2CH2OCO-等。
烷硫基:直链或支链烷基,经硫原子键连接到结构上。
卤代烷硫基:直链或支链烷硫基,在这些烷基上的氢原子可部分或全部被卤原子所取代。例如,氯甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基等。
烷硫基烷基:烷基-S-烷基-,例如CH3SCH2-。
卤代烷硫基烷基:烷硫基烷基的烷基上的氢原子可部分或全部被卤原子所取代,如ClCH2CH2SCH2-、CF3CH2SCH2-等。
烷基氨基:直链或支链烷基,经氮原子键连接到结构上。
卤代烷基氨基:直链或支链烷基氨基,在这些烷基上的氢原子可部分或全部被卤原子所取代。
二烷基氨基:如(CH3)2N-,(CH3CH2)2N-。
卤代二烷基氨基:烷基上的氢原子可部分或全部被卤原子所取代,如(CF3)2N-,(CF3CH2)2N-。
烯基:直链或支链烯类,例如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体。烯基还包括多烯类,如1,2-丙二烯基和2,4-己二烯基。
卤代烯基:直链或支链烯类,在这些烯基上的氢原子可部分或全部被卤原子所取代。
烯氧基:直链或支链烯类,经氧原子键连接到结构上。
卤代烯氧基:直链或支链烯氧基,在这些烯氧基上的氢原子可部分或全部被卤原子所取代。
烯基硫基:直链或支链烯类,经硫原子键连接到结构上。如CH2=CHCH2S-。
烯氧基羰基:如CH2=CHCH2OCO-等。
炔基:直链或支链炔类,例如乙炔基、1-丙炔基、2-丙炔基和不同的丁炔基、戊炔基和己炔基异构体。炔基还包括由多个三键组成的基团,如2,5-己二炔基。
卤代炔基:直链或支链炔类,在这些炔基上的氢原子可部分或全部被卤原子所取代。
炔氧基:直链或支链炔类,经氧原子键连接到结构上。
卤代炔氧基:直链或支链炔氧基,在这些炔氧基上的氢原子可部分或全部被卤原子所取代。
炔氧基羰基:如CH≡CCH2OCO-等。
烷基磺酰基:直链或支链烷基经磺酰基(-SO2-)连接到结构上,如甲基磺酰基。
卤代烷基磺酰基:直链或支链烷基磺酰基,其烷基上的氢原子可部分或全部被卤原子所取代。
烷基羰基:烷基经羰基连接到结构上,如CH3CO-,CH3CH2CO-。
卤代烷基羰基:烷基羰基的烷基上的氢原子可部分或全部被卤原子所取代,如CF3CO-。
烷氧基羰基:烷氧基经羰基连接到结构上。如CH3OCO-,CH3CH2OCO-。
氨基羰基:如NH2CO-,
烷基氨基羰基:烷基-NH-CO-,例如CH3NHCO-,CH3CH2NHCO-。
二烷基氨基羰基:如(CH3)2NCO-,(CH3CH2)2NCO-。
(杂)芳基、(杂)芳基烷基、(杂)芳基羰基、(杂)芳甲基羰基、(杂)芳基羰基烷基、(杂)芳氧基羰基、(杂)芳基烷基氧基羰基中的芳基部分包括苯基或萘基等。杂芳基是含1个或多个N、O、S杂原子的五元环或六元环。例如呋喃基、吡唑基、噻唑基、吡啶基、嘧啶基、吡嗪基、哒嗪基、三嗪基、喹啉基等。
(杂)芳基:如苯基等。
(杂)芳基烷基:如苯甲基、苯乙基、对氯苯甲基、2-氯吡啶-5-基、2-氯-噻唑-5-基等。
(杂)芳基羰基:如苯甲酰基、4-氯苯甲酰基等。
(杂)芳甲基羰基:如PhCH2CO-
(杂)芳基羰基烷基:如PhCOCH2-。
(杂)芳氧基羰基:如苯氧基羰基、4-氯苯氧基羰基、4-硝基苯氧基羰基、萘氧基羰基等。芳基烷基氧基羰基:如苄基氧基羰基、4-氯苄基氧基羰基、4-三氟甲基苄基氧基羰基等。
(杂)芳基烷基氧基羰基:如PhCH2OCO-、4-Cl-PhCH2OCO-等。
表1、表2、表3、表4、表5、表6、表7、表8分别列举了通式I中R1、R2、R3(X=NR3)、R4和R5、R6和R7、R8、R9、W的部分具体取代基,但它们并非仅限于这些取代基。
表1 R1取代基
表2 R2取代基
R2 | R2 | R2 | R2 |
H | F | Cl | Br |
I | CN | NO2 | NH2 |
CHO | CH3 | C2H5 | n-C3H7 |
i-C3H7 | n-C4H9 | s-C4H9 | i-C4H9 |
t-C4H9 | OCH3 | OC2H5 | OC3H7-n |
OC3H7-i | OC4H9-n | OC4H9-i | OC4H9-t |
OCH2F | OCHF2 | OCF3 | OCH2CF3 |
表3 R3取代基
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表4 R4(R5)取代基
表5 R6(R7)取代基
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表6 R8取代基
R8 | R8 | R8 | R8 |
H | CN | CH3 | C2H5 |
n-C3H7 | i-C3H7 | n-C4H9 | s-C4H9 |
i-C4H9 | t-C4H9 | CF3 | CCl3 |
CHF2 | CH2F | CH2Cl | CH2CF3 |
CF2CF3 | COOCH3 | Ph | Ph-4-Cl |
表7 R9取代基
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表8 W取代基
本发明的部分化合物可以用表9-表82中列出的具体化合物来说明,但并不限定本发明。表中涉及的通式化合物IA、IB、IC、ID、IE、IF、IG、IH、II、IJ、IK、IL、IM、IN、IO、IP、IQ或IR中,W=R6=R7=R8=R22=R23=R24=R25=R26=H;
具体为:
通式IA中,
当R1=Cl、R2=Cl、R3=R4=R5=H时,R13取代基见表9,代表化合物编号依次为9-1—9-15。
表9
表10:通式IA中,当R1=CH3、R2=Cl、R3=R4=R5=H时,取代基R13与表9中所示取代基一致,代表化合物编号依次为10-1—10-15。
表11:通式IA中,当R1=C2H5、R2=Cl、R3=R4=R5=H时,取代基R13与表9中所示取代基一致,代表化合物编号依次为11-1—11-15。
表12:通式IA中,当R1=CHF2、R2=Cl、R3=R4=R5=H时,取代基R13与表9中所示取代基一致,代表化合物编号依次为12-1—12-15。
表13:通式IA中,当R1=CF3、R2=Cl、R3=R4=R5=H时,取代基R13与表9中所示取代基一致,代表化合物编号依次为13-1—13-15。
表14:通式IA中,当R1=Cl、R2=Cl、R3=R4=H、R5=CH3时,取代基R13与表9中所示取代基一致,代表化合物编号依次为14-1—14-15。
表15:通式IA中,当R1=CH3、R2=Cl、R3=R4=H、R5=CH3时,取代基R13与表9中所示取代基一致,代表化合物编号依次为15-1—15-15。
表16:通式IA中,当R1=C2H5、R2=Cl、R3=R4=H、R5=CH3时,取代基R13与表9中所示取代基一致,代表化合物编号依次为16-1—16-15。
表17:通式IA中,当R1=CHF2、R2=Cl、R3=R4=H、R5=CH3时,取代基R13与表9中所示取代基一致,代表化合物编号依次为17-1—17-15。
表18:通式IA中,当R1=CF3、R2=Cl、R3=R4=H、R5=CH3时,取代基R13与表9中所示取代基一致,代表化合物编号依次为18-1—18-15。
通式IB中,
当R1=Cl、R2=Cl、R3=R4=R5=H时,R14、R15取代基见表19,代表化合物编号依次为19-1—19-10。
表19
编号 | R14 | R15 |
19-1 | H | H |
19-2 | H | Br |
19-3 | H | CH3 |
19-4 | H | NO2 |
19-5 | H | CN |
19-6 | H | CF3 |
19-7 | Cl | H |
19-8 | CH3 | H |
19-9 | CF3 | H |
19-10 | CF3 | CO2CH3 |
表20:通式IB中,当R1=CH3、R2=Cl、R3=R4=R5=H时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为20-1—20-10。
表21:通式IB中,当R1=C2H5、R2=Cl、R3=R4=R5=H时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为21-1—21-10。
表22:通式IB中,当R1=CHF2、R2=Cl、R3=R4=R5=H时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为22-1—22-10。
表23:通式IB中,当R1=CF3、R2=Cl、R3=R4=R5=H时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为23-1—23-10。
表24:通式IB中,当R1=Cl、R2=Cl、R3=R4=H、R5=CH3时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为24-1—24-10。
表25:通式IB中,当R1=CH3、R2=Cl、R3=R4=H、R5=CH3时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为25-1—25-10。
表26:通式IB中,当R1=C2H5、R2=Cl、R3=R4=H、R5=CH3时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为26-1—26-10。
表27:通式IB中,当R1=CHF2、R2=Cl、R3=R4=H、R5=CH3时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为27-1—27-10。
表28:通式IB中,当R1=CF3、R2=Cl、R3=R4=H、R5=CH3时,取代基R14、R15与表19中所示取代基一致,代表化合物编号依次为28-1—28-10。
通式IC中,
当R1=Cl、R2=Cl、R3=R4=R5=H时,(R10)n取代基见表29,代表化合物编号依次为29-1—29-279。
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表30:通式IC中,当R1=Cl、R2=CH3、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为30-1—30-279。
表31:通式IC中,当R1=Cl、R2=OCH3、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为31-1—31-279。
表32:通式IC中,当R1=Cl、R2=CHO、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为32-1—32-279。
表33:通式IC中,当R1=Cl、R2=Br、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为33-1—33-279。
表34:通式IC中,当R1=CH3、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为34-1—34-279。
表35:通式IC中,当R1=C2H5、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为35-1—35-279。
表36:通式IC中,当R1=CHF2、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为36-1—36-279。
表37:通式IC中,当R1=CF3、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为37-1—37-279。
表38:通式IC中,当R1=Cl、R2=Cl、R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为38-1—38-279。
表39:通式IC中,当R1=CH3、R2=Cl、R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为39-1—39-279。
表40:通式IC中,当R1=C2H5、R2=Cl、R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为40-1—40-279。
表41:通式IC中,当R1=CHF2、R2=Cl、R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为41-1—41-279。
表42:通式IC中,当R1=CF3、R2=Cl、R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为42-1—42-279。
表43:通式IF中,当R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为43-1—43-279。
表44:通式IF中,当R3=R4=H、R5=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为44-1—44-279。
表45:通式IG中,当R3=R4=R5=H,R27=Cl时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为45-1—45-279。
表46:通式IG中,当R3=R4=R5=H,R27=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为46-1—46-279。
表47:通式IG中,当R3=R4=H、R5=CH3,R27=Cl时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为47-1—47-279。
表48:通式IG中,当R3=R4=H、R5=CH3,R27=CH3时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为48-1—48-279。
表49:通式IC中,当R1=CH3、R2=Cl、R3=R4=H、R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为49-1—49-279。
表50:通式IC中,当R1=C2H5、R2=Cl、R3=R4=H、R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为50-1—50-279。
表51:通式IC中,当R1=CHF2、R2=Cl、R3=R4=H、R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为51-1—51-279。
表52:通式IC中,当R1=CH3、R2=Cl、R3=R4=R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为52-1—52-279。
表53:通式IC中,当R1=C2H5、R2=Cl、R3=R4=R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为53-1—53-279。
表54:通式IC中,当R1=CHF2、R2=Cl、R3=R4=R5=F时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为54-1—54-279。
表55:通式IH中,当R3=R4=R5=H、R28=CH3、R29=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为55-1—55-279。
表56:通式II中,当R3=R4=R5=H、R30=CH3、R31=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为56-1—56-279。
表57:通式IJ中,当R3=R4=R5=H、R32=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为57-1—57-279。
表58:通式IK中,当R3=R4=R5=H、R33=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为58-1—58-279。
表59:通式IL中,当R3=R4=R5=H、R34=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为59-1—59-279。
表60:通式IM中,当R3=R4=R5=H、R35=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为60-1—60-279。
通式IN中,
IN(X=O或S)
表61:通式IN中,当R1=CH3、R2=Cl、R3=R4=R5=H、X=O时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为61-1—61-279,依次对应表29的29-1—29-279。
表62:通式IN中,当R1=C2H5、R2=Cl、R3=R4=R5=H、X=O时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为62-1—62-279,依次对应表29的29-1—29-279。
表63:通式IN中,当R1=CHF2、R2=Cl、R3=R4=R5=H、X=O时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为63-1—63-279,依次对应表29的29-1—29-279。
表64:通式IN中,当R1=CH3、R2=Cl、R3=R4=R5=H、X=S时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为64-1—64-279,依次对应表29的29-1—29-279。
表65:通式IN中,当R1=C2H5、R2=Cl、R3=R4=R5=H、X=S时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为65-1—65-279,依次对应表29的29-1—29-279。
表66:通式IN中,当R1=CHF2、R2=Cl、R3=R4=R5=H、X=S时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为66-1—66-279,依次对应表29的29-1—29-279。
表67:通式IO中,当R1=Cl、R2=Br、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为67-1—67-279。
表68:通式IO中,当R1=Cl、R2=NH2、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为68-1—68-279。
表69:通式IO中,当R1=Cl、R2=NO2、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为69-1—69-279。
表70:通式IO中,当R1=Cl、R2=CHO、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为70-1—70-279。
表71:通式IO中,当R1=Cl、R2=CH3、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为71-1—71-279。
表72:通式IO中,当R1=Cl、R2=OCH3、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为72-1—72-279。
表73:通式IO中,当R1=CH3、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为73-1—73-279。
表74:通式IO中,当R1=C2H5、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为74-1—74-279。
表75:通式IO中,当R1=CHF2、R2=Cl、R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为75-1—75-279。
表76:通式IP中,当R3=R4=R5=H时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为76-1—76-279。
表76-2:通式IP中,当R3=R4=R5=H,R24=Br时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为76-2-1—76-2-279。
表77:通式IQ中,当R3=R4=R5=H,R27=Cl时,取代基(R10)n与表29中所示取代基一致,代表化合物编号依次为77-1—77-279。
通式IC中,当R1=C2H5、R2=Cl、R4=R5=H、(R10)n=H时,取代基R3(不为氢时)为不同的取代基见表78,代表化合物编号依次为78-1—78-140。
表78
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通式IR中,
通式IR中,当R1=CH3、R2=Cl、R3=R4=R5=H、m=1时,取代基Het1见表80,代表化合物编号依次为80-1—80-15。
表80 Het1取代基
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表81:通式IR中,当R1=C2H5、R2=Cl、R3=R4=R5=H、m=1时,取代基Het1与表80中所示取代基一致,代表化合物编号依次为81-1—81-15。
表82:通式IR中,当R1=CHF2、R2=Cl、R3=R4=R5=H、m=1时,取代基Het1与表80中所示取代基一致,代表化合物编号依次为82-1—82-15。
表83:通式IR中,当R1=CH3、R2=Cl、R3=R4=R5=H、m=2时,取代基Het1与表80中所示取代基一致,代表化合物编号依次为83-1—83-15。
表84:通式IR中,当R1=C2H5、R2=Cl、R3=R4=R5=H、m=2时,取代基Het1与表80中所示取代基一致,代表化合物编号依次为84-1—84-15。
表85:通式IR中,当R1=CHF2、R2=Cl、R3=R4=R5=H、m=2时,取代基Het1与表80中所示取代基一致,代表化合物编号依次为85-1—85-15。
本发明通式I部分化合物的盐可以用表79中列出的具体化合物的盐来说明,但并不限定本发明。
表79部分化合物盐
本发明化合物按照以下方法制备,反应式如下,式中各基团除另有说明外定义同前:
通式化合物I的制备根据Y的定义不同,分为以下两种情况:
(1)当Y=O时,通式化合物I-1的制备方法如下:
中间体II和III在碱性条件下于适宜的溶剂中反应得到通式I-1化合物。
适宜的碱可选自如氢氧化钾、氢氧化钠、碳酸钠、碳酸钾、碳酸氢钠、三乙胺、吡啶、甲醇钠、乙醇钠、氢化钠、叔丁醇钾或叔丁醇钠等。
反应在适宜的溶剂中进行,适宜的溶剂可选自如四氢呋喃、1,4-二氧六环、乙腈、甲苯、二甲苯、苯、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二甲亚砜、丙酮或丁酮等。
反应温度可在室温至溶剂沸点温度之间,通常为20-100℃。
应时间为30分钟至20小时,通常1-10小时。
中间体II部分有市售,也可以按公知方法制备,例如参照文献JP2000007662、US4977264、US6090815、US20040092402、JP09124613、US5468751、US4985426、US4845097、Recueil des Travaux Chimiques des Pays-Bas(1978),97(11),Pages288-92、Journalof the American Chemical Society,79,1455(1957)、Journal of Chemical Society,p.3478-3481(1955)描述的方法制备。
中间体Ⅲ是制备本发明通式I-1化合物的关键中间体,按以下方法制备:
X-1与相应的卤化物反应制得III,此步骤操作方法参照US20100158860、WO2011133444和Bioorganic&Medicinal Chemistry,20(20),6109-6122,2012。
中间体来源如下:中间体X-1参照如下报道的方法制备,或是部分中间体X-1经市售获得;
当Het为1,2,3-三唑基时,参照BR 102013026761;Helvetica Chimica Acta(1962),45,2441-62;Helvetica Chimica Acta(1962),45,2426-41;Tetrahedron Letters(1962),917-19;等制备;
当Het为1,2,4-噻二唑基时,参照Chemiker-Zeitung(1976),100(11),497-8等制备;
当Het为1,2,3-噻二唑基时,参照Journal of the Chemical Society,PerkinTransactions 1:Organic and Bio-Organic Chemistry(1972-1999)(1979),(4),956-9等制备;
当Het为1,3,4-噻二唑基时,参照Bulletin de la Societe Chimique deFrance,(1),62-5,1985;Helvetica Chimica Acta,65(8),2606-21,1982;等制备;
当Het为1,3,4-恶二唑基时,参照Journal of Organic Chemistry,80(11),5713-5718;2015;Green Chemistry,17(8),4300-4306;2015;RSC Advances,5(80),65351-65357;2015等制备;
当Het为1,2,4-三唑时,参照Journal of Heterocydic Chemistry,25(5),1467-1470,1988;US20020037905、WO2013093484、US20140364414等制备,路线如下:
上述反应的适宜温度优选0~50℃;反应时间为30分钟至20小时,优选0.5~10小时。
适宜的溶剂选自乙酸乙酯、乙酸甲酯、甲酸甲酯、苯、甲苯、二甲苯、氯仿、二氯甲烷、水、四氢呋喃、乙腈、二噁烷、N,N-二甲基甲酰胺、N-甲基吡咯烷酮或二甲亚砜等。
适宜的碱可选自如氢氧化钾、氢氧化钠、碳酸钠、碳酸钾、碳酸氢钠、三乙胺、吡啶、甲醇钠、乙醇钠、氢化钠、叔丁醇钾或叔丁醇钠等。
(2)当Y=NR3或S时,通式化合物I-2可按如下通式制备。中间体IV的具体制备方法可参考Journal of the Institution of Chemists(India),79(2),54-57;2007、WO2003049739、WO2000031072等。
虽然本发明的通式I化合物与现有技术中公开的某些化合物也属于含嘧啶的取代唑类化合物,但结构特征仍存在显著不同。并且由于这些结构上的差异而使得本发明的化合物具有更好的杀菌和/或杀虫杀螨活性。
通式I化合物对农业或其他领域中的多种病菌显示出优异的活性,对害虫害螨也显示出较好的活性。因此,本发明的技术方案还包括通式I化合物在农业或其他领域中用作制备杀菌剂、杀虫杀螨剂的用途。
下面提及的病害的例子仅用来说明本发明,但绝不限定本发明。
通式I化合物可用于防治下列病害:卵菌纲病害,如霜霉病(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、白菜类霜霉病、菠菜霜霉病、萝卜霜霉病、葡萄霜霉病、葱霜霉病),白锈菌(油菜白锈病、白菜类白锈病),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、南瓜疫病、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(马铃薯晚疫病、番茄晚疫病)等;半知菌病害,如枯萎病(甘薯枯萎病、棉花枯萎病、芝麻枯萎病、蓖麻枯萎病、番茄枯萎病、菜豆枯萎病、黄瓜枯萎病、丝瓜枯萎病、南瓜枯萎病、冬瓜枯萎病、西瓜枯萎病、甜瓜枯萎病、辣椒枯萎病、蚕豆枯萎病、油菜枯萎病、大豆枯萎病),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、棉黑根腐病、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),炭疽病(高粱炭疽病、棉花炭疽病、红麻炭疽病、黄麻炭疽病、亚麻炭疽病、烟草炭疽病、桑炭疽病、辣椒炭疽病、茄子炭疽病、菜豆炭疽病、黄瓜炭疽病、苦瓜炭疽病、西葫芦炭疽病、冬瓜炭疽病、西瓜炭疽病、甜瓜炭疽病、荔枝炭疽病),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(棉铃灰霉病、红麻灰霉病、番茄灰霉病、辣椒灰霉病、菜豆灰霉病、芹菜灰霉病、菠菜灰霉病、猕猴桃灰霉病),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、胡萝卜黑腐病、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、红麻腰折病、稻瘟病、栗黑鞘病、甘蔗眼斑病、棉铃曲霉病、花生冠腐病、大豆茎枯病、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、芹菜黑腐病、菠菜心腐病、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、菜豆炭腐病、大豆靶点病、茄子棒孢叶斑病、黄瓜靶斑病、番茄叶霉病、茄子叶霉病、蚕豆赤斑病等)等;担子菌病害,如锈病(小麦条锈病、小麦杆锈病、小麦叶锈病、花生锈病、向日葵锈病、甘蔗锈病、韭菜锈病、葱锈病、栗锈病、大豆锈病),黑穗病(玉米丝黑穗病、玉米黑粉病、高粱丝黑穗病、高粱散黑穗病、高粱坚黑穗病、高梁柱黑粉病、栗粒黑穗病、甘蔗黑穗病、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、油菜白粉病、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)等。特别地,对黄瓜霜霉病、玉米锈病和黄瓜炭疽病,在较低剂量下仍具有很好的防治效果。
通式I化合物可用于防治下列害虫:
鞘翅目(Coleoptera)(甲虫):豆象属种(Acanthoscelides spp.)(象虫)、菜豆象(Acanthoscelides obtectus)(普通豌豆象)、白蜡窄吉丁(Agrilus planipennis)(花曲柳窄吉丁)、金针虫属种(Agriotes spp.)(金针虫)、光肩星天牛(Anoplophoraglabripennis)(亚洲长角天牛)、棉铃象属种(Anthonomus spp.)(象甲科)、墨西哥棉铃象(Anthonomus grandis)(棉铃虫)、茧蜂属种(Aphidius spp.)、象甲属种(Apion spp.)(象虫)、甘蔗金龟属种(Apogonia spp.)(蛴螬)、黑绒金龟(Atacnius sprctulus)(黑绒金龟子)、甜菜隐食甲(Atomaria linearis)(小甜菜甲虫(pygmy mangold beetle)、守瓜属种(Aulacophore spp.)、甜菜象(Bothynoderes punctiventris)(甜菜根象虫)、豆象属种(Bruchus spp.)(象虫)、豌豆象(Bruchus pisorum)(豌豆象虫)、Cacoesia属种(Cacoesiaspp.)、四纹豆象(Callosobruchus maculatus)(南方豇豆象虫)、黄斑露尾甲(Carpophilushemipteras)(干果甲虫)、甜菜龟甲(Cassida vittata)、天牛属种(Ccrostcrna spp.),Ccrotoma属种(Ccrotoma spp.)(金滴虫(chrysomcids))、豆叶甲(Cerotoma trifur cata)(豆叶甲虫)、龟象属种(Ceutorhynchus spp.)(象虫)、白菜籽龟象(Ceutorhynchusassimilis)(白菜象鼻虫(cabbage seedpod weevil))、芜菁龟象(Ceutorhynchus napi)(卷心菜象虫(cabbage curculio))、跳甲属种(Chaetocnema spp.)(金滴虫)、Colaspis属种(Colaspis spp.)(土甲虫)、Conoderus scalaris、Conoderus stigmosus、李象(Conotrachelus nenuphar)(梅锥象甲),Cotinus nitidis(绿花金龟(Green Junebeetle))、石刁柏负泥虫(Crioceris asparagi)(石刁柏甲虫)、锈赤扁谷盗(Cryptolestesferrugincus)(锈谷甲虫(rusty grainbeetle))、长角扁谷盗(Cryptolestes pusillus)(扁谷盗)、土耳其扁谷盗(Cryptolestes turcicus)(土耳其谷甲虫(Turkish grainbeetle))、Ctenicera属种(Ctenicera spp.)(线虫)、象虫属种(Curculio spp.)(象虫)、圆头犀金龟属种(Cyclocephala spp.)(蛴螬)、密点细枝象(Cylindrocpturus adspersus)(向日葵草象虫(sunflower stem weevil))、芒果剪叶象(Deporaus marginatus)(芒果剪叶象虫(mango leaf-cutting weevil))、火腿皮蠢(Dermestes lardarius)(火腿皮蠢)、白腹皮蠢(Dermestes maculates)(白腹皮蠢)、叶甲属种(Diabrotica spp.)(叶甲)、墨西哥豆瓢虫(Epilachna varivcstis)(墨西哥豆甲虫)、蛀茎象甲(raustinus cubae)、苍白根颈象(Hylobius pales)(好斗象甲(pales weevil))、叶象属种(Hypera spp.)(象虫)、紫苜蓿叶象(Hypera postica)(紫苜蓿象鼻虫)、Hyperdoes属种(Hyperdoes spp.)(阿根廷茎象甲(Hyperodes weevil))、咖啡果小蠢(Hypothenemus hampei)(咖啡果甲虫)、齿小蠢属种(Ips spp.)(棘胫小蠢(engravers))、烟草甲(Lasioderma serricorne)(烟草甲虫)、马铃薯甲虫(Leptinotarsa decemlineata)(科罗拉多马铃薯甲虫)、Liogenys fuscus、Liogenys suturalis、稻水象甲(Lissorhoptrus oryzophilus)(稻水象甲)、粉蠢属种(Lyctus spp.)(木蠢蛾/粉蠢甲虫(powder post beetles))、Maecolaspis joliveti,Megascelis属种(Megascelis spp.)、玉米叩甲(Melanotus communis)、露尾甲属种(Meligethes spp.)、油菜露尾甲(Meligethes aeneus)(花金龟(blossom beetle))、五月金龟子(Melolontha melolontha)(普通欧洲金龟子)、Oberea brevis、线形筒天牛(Oberealinearis)、椰蛀犀金龟(Oryctes rhinoceros)(椰枣甲虫(date palm beetle))、贸易锯谷盗(Oryzaephilus mercator)(市场锯谷盗(merchant grain beetle))、锯谷盗(Oryzaephilus surinamensis)(锯齿谷甲虫(sawtoothcd grain bcctlc))、喙象甲属种(Otiorhynchus spp.)(象虫)、黑角负泥虫(Oulema melanopus)(橙足负泥虫(cerealleafbeetle))、水稻负泥虫(Oulema oryzae)、玫瑰短喙象属种(Pantomorus spp.)(象虫)、食叶鳃金龟属种(Phyllophaga spp.)(五月/六月金龟子),Phvllophaga cuyabana、黄条跳甲属种(Phyllotreta spp.)(金滴虫)、苹虎象属种(Phynchites spp.)、日本弧丽金龟(Popillia japonica)(日本金龟子)、大谷蠢(Prostephanus truncates)(大谷长蠢(larger grain borer))、谷蠢(Rhizopertha dominica)(谷小蛀虫(lesser grainborer))、根鳃金龟属种(Rhizotrogus spp.)(欧洲金龟子(Eurpoean chafer))、隐喙象属种(Rhynchophorus spp.)(象虫)、小蠢属种(Scolytus spp.)(木蠢蛾)、Shenophorus属种(Shenophorus spp.)(谷象)、豌豆叶象(Sitona lincatus)(豌豆叶象甲(pca leafweevil))、米象属种(Sitophilus spp.)(谷象甲)、谷象(Sitophilus granaries)(谷虫(granary weevil))、米象(Sitophilus oryzae)(米象甲(rice weevil))、药材谷盗(Stegobium paniceum)(药材甲(drugstore beetle))、拟谷盗属种(Tribolium spp.)(面象虫)、赤拟谷盗(Tribolium castaneum)(赤拟谷盗(red flour beetle))、杂拟谷濡(Tribolium confusum)(杂拟谷盗(confused flour beetle))、花斑皮蠢(Trogodermavariabile)(仓库皮蠢(warehouse beetle))和Zabrus tenebioides。
革翅目(Dcrmaptcra)(蠼螋)。
脉翅目(Dictyoptera)(蟑螂):德国小蠊(Blattella germanica)(德国小蠊(German cockroach))、东方蜚蠊(Blatta orientalis)(东方蠊)、宾夕法尼亚木蠊(Parcoblatta pennylvanica)、美洲大蠊(Periplaneta americana)(美洲蜚痨(Americancockroach))、澳洲大蠊(Periplaneta australoasiae)(澳洲大蠊(Australiancockroach))、褐色大蠊(Pcriplancta brunnca)(褐色大蠊(brown cockroach))、烟色大蠊(Periplaneta fuliginosa)(黑胸大蠊(smokybrown cockroach))、蔗绿蜚蠊(Pyncoselussuninamensis)(蔗蠊(Surinam cockroach))和长须蜚蠊(Supella longipalpa)(褐带蜚蠊(brownbanded cockroach))。
双翅目(Diptera)(苍蝇):伊蚊属种(Aedes spp.)(蚊)、紫苜蓿潜蝇(Agromyzafrontella)(紫苜蓿潜蝇(alfalfa blotch leafminer))、潜蝇属种((Agromyza spp.)(潜叶蝇)、按实蝇属种(Anastrepha spp.)(果蝇)、加勒比按实蝇(Anastrepha suspensa)(加勒比按实蝇(Caribbean fruit fly))、疟蚊属种(Anopheles spp.)(蚊)、果实蝇属种(Batrocera spp.)(果蝇)、瓜实蝇(Bactrocera cucurbitae)(瓜蝇)、桔小实蝇(Bactrocera dorsalis)(桔实蝇)、小条实蝇属种(Ceratitis spp.)(果蝇)、地中海小条实蝇(Ceratitis capitata)(地中海果蝇)、斑虻属种(Chrysops spp.)(鹿虻)、锥蝇属种(Cochliomyia spp.)(旋丽蝇幼虫)、廮蚊属种(Contarinia spp.)(廮蚊)、库蚊属种(Culexspp.)(蚊)、叶廮蚊属种(Dasineura spp.)(廮蚊)、油菜叶廮蚊(Dasineura brassicae)(卷心菜廮蚊)、地种蝇属种(Delia spp.)、灰地种蝇(Delia platura)(根蛆(seedcornmaggot))、果蝇属种(Drosophila spp.)(醋蝇)、厕蝇属种(Fannia spp.)(家蝇)、黄腹厕蝇(Fannia canicularis)(夏厕蝇(little house fly))、灰腹厕蝇(Fannia scalaris)(灰腹厕蝇)、大马胃蝇(Gasterophilus intestinalis)(马胃蝇)、Gracillia perseae、扰血蝇(Haematobia irritans)(角蝇)、黑蝇属种(Hylemyia spp.)(根蛆(root maggot))、纹皮蝇(Hypoderma lineatum)(普通纹皮蝇(common cattle grub))、斑潜蝇属种(Liriomyzaspp.)(潜叶蝇)、甘蓝斑潜蝇(Liriomyza brassica)(蛇行潜叶蝇(serpentineleafminer))、绵羊虱蝇(Melophagus ovinus)(绵羊蜱)、蝇属种(Musca spp.)(家蝇(muscid fly))、秋家蝇(Musca autumnalis)(秋家蝇(face fly))、家蝇(Vuscadomestica)(家蝇(house fly))、羊狂蝇(Oestrus ovis)(羊鼻蝇(sheep bot fly))、欧洲麦秆蝇(Oscinella frit)(瑞典麦秆蝇)、甜菜泉蝇(Pegomyia betae)(菠菜潜叶蝇(beetleafminer))、麦蝇属种(Phorbia spp.)、胡萝卜茎蝇(Psila rosae)(胡萝卜锈蝇(carrotrust fly))、樱桃果蝇(Rhagoletis cerasi)(樱桃果蝇(cherry fruit fly))、苹果实蝇(Rhagoletis pomonella)(苹果蛆(apple maggot))、麦红吸浆虫(Sitodiplosismosellana)(橙色小麦花蚊(orange wheat blossom midge))、厩螫蝇(stomoxyscalcitruns)(厩螫蝇(stable fly))、牛虻属种(Tahanus spp.)(马蝇)和大蚊属种(Tipulaspp.)(大蚊)。
半翅目(Hemiptera)(蝽):拟绿蝽(Acrosternum hilare)(绿蝽(green stinkbug))、美洲谷长蝽(Blissus leucopterus)(长蝽(chinch bug))、马铃薯俊盲蝽(Calocoris norvegicus)(马铃薯盲蝽(potato mirid))、热带臭虫(Cimex hemipterus)(热带臭虫(tropical bed bug))、臭虫(Cimex lectularius)(臭虫(bed hug))、Daghertusfasciatus、Dichelops furcatus、棉黑翅红蝽(Dysdercus suturellus)(棉红蝽(cottonstainer))、Edessa meditabunda、欧扁盾蝽(Eurygaster maura)(谷虫(cereal bug))、Euschistus heros、褐臭蝽(Euschistus servus)(褐蝽(brown stink bug))、安氏角盲蝽(Helopeltis antonii)、茶角盲蝽(Helopeltis theivora)(tea blight plantbug)、蝽属种(Lagynotomus spp.)(蝽)、大稻缘蝽(Leptocorisa oratorius)、异稻缘蝽(Leptocorisavaricornis)、草盲蝽属种(Lygus spp.)(盲蝽(plant bug))、豆荚草盲蝽(Lygushesperus)(western tarnished plant bug)、木槿曼粉蝽(Maconellicoccus hirsutus)、Neurocolpus longirostris、稻绿蝽(Nezara viridula)(southern green stink bug)、植盲蝽属种(PhyLocoris spp.)(盲蝽)、加利福尼亚植盲蝽(Phytocoris californicus)、Phytocoris relativus,、Piezodorus guildingi、四线盲蝽(Poecilocapsus lineatus)(fourlined plant bug)、Psallus vaccinicola、Pseudacysta perseae、Scaptocoriscastanea和锥蝽属种(Triatoma spp.)(吸血锥鼻虫(bloodsuckingconenose bug)/猎蝽(kissing bug))。
同翅目(Homoptera)(蚜虫、蚧、粉虱、叶蝉):豌豆蚜(Acrythosiphonpisum)(豌豆蚜(pea aphid))、球蚜属种(Adelges spp.)(adelgids)、甘蓝粉虱(Aleurodesproletella)(卷心菜粉虱)、螺旋粉虱(Aleurodicus disperses)、丝绒粉虱(Aleurothrixus flccosus)(棉粉虱(woolly whitefly))、白轮盾蚧属种(Aluacaspisspp.)、Amrasca bigutella bigutella、沫蝉属种(Aphrophora spp.)(叶蝉(leafhopper))、红圆蚧(Aonidiella aurantii)(加利福尼亚红蚧(California redscale))、蚜虫属种(Aphis spp.)(蚜虫)、棉蚜(Aphis gossypii)(cotton aphid)、苹果蚜(Aphis pomi)(apple aphid)、茄无网蚜(Aulacorthitm solani)(毛地黄蚜(foxgloveaphid))、粉虱属种(Bemisia spp.)(粉虱)、银叶粉虱(Bemisia argentifolii)、甘薯粉虱(Bemisia tabaci)(sweetpotato whitefly)、麦双尾蚜(Brachycolus noxius)(俄罗斯蚜(Russian aphid))、石刁柏小管蚜(Brachycorynclia asparagi)(石刁柏蚜(asparagusaphid))、Brevennia rehi、甘蓝蚜(Brevicoryne brassicae)(卷心菜蚜)、蜡蚧属种(Ceroplastes spp.)(蚧)、红蜡蚧(Ceroplastes rubens)(red wax scale)、雪盾蚧属种(Chionaspis spp.)(蚧)、圆盾蚧属种(Chrysomphalus spp.)(蚧)、软蜡蚧属种(Coccusspp.)(蚧)、苹粉红劣蚜(Dysaphis plantaginea)(rosy apple aphid)、绿小叶蝉属种(Empoasca spp.)(叶蝉)、苹果棉蚜(Eriosoma lanigerum)(woolly apple aphid)、吹棉蚧(Icerya purchasi)(cottony cushion scale)、芒果黄线叶蝉(Idioscopus nitidulus)(mango leafhopper)、灰飞虱(Laodelphax striatellus)(smaller brown planthopper)、蛎盾蚧属种(Lepidosaphes spp.)、长管蚜属种(Macrosiphum spp.)、大戟长管蚜(Macrosiphum euphorbiae)(马铃薯蚜(potato aphid))、麦长管蚜(Macrosiphumgranarium)(英国麦蚜(English grain aphid))、蔷薇长管蚜(Macrosiphum rosae)(蔷薇蚜(rose aphid))、四线叶蝉(Macrosteles quadrilineatus)(紫莞叶蝉(asterleafhopper))、Mahanarva frimbiolata、麦无网长管蚜(Metopolophium dirhodum)(蔷薇麦蚜(rose grain aphid))、Midis longicornis、桃蚜(Myzus persicae)(桃蚜(greenpeach aphid))、黑尾叶蝉属种(Nephotettix spp.)(叶蝉)、黑尾叶蝉(Nephotettixcinctipes)(绿叶蝉(green leafhopper))、褐飞虱(Nilaparvata lugens)(brownplanthopper)、糠片盾蚧(Parlatoria pergandii)(chaff scale)、黑檀盾蚧(Parlatoriaziziphi)(ebony scale)、玉米花翅飞虱(Peregrinus maidis)(corn delphacid)、沫蝉属种(Philaenus spp.)(吹沫虫)、葡萄根瘤蚜(Phylloxera vitifoliae)(grapephylloxera)、去杉球蚧(Physokermes piceae)(spruce bud scale)、臀纹粉蚧属种(Planococcus spp.)(粉蚧)、粉蚧属种(Pseudococcus spp.)(粉蚧)、菠萝洁粉蚧(Pscudococcus brcvipcs)(pinc apple mcalybug)、梨园盾蚧(Quadraspidiotusperniciosus)(圣约瑟虫(San Jose scale))、蚜蚧属种(Rhapalosiphum spp.)(蚜虫)、玉米叶蚜(Rhapalosiphum maida)(玉米蚜(corn leaf aphid))、禾谷缢管蚜(Rhapalosiphumpadi)(oatbird-cherry aphid)、珠蜡蚧属种(Saissetia spp.)(蚧)、榄珠蜡蚧(Saissetiaoleae)(黑蚧)、麦二叉蚜(Schizaphis graminum)(麦二叉蚜(gr eenbug))、麦长管蚜(Sitobion avenge)(英国麦蚜)、白背飞虱(Sogatella furcifera)(white-backedplanthopper)、彩斑蚜属种(Therioaphis spp.)(蚜虫)、纹蜡蚧属种(Toumeyella spp.)(蚧)、声蚜属种(Toxoptera spp.)(蚜虫)、白粉虱属种(Trialeurodes spp.)(粉虱)、温室白粉虱(Trialeurodes vaporariorum)(温室粉虱(greenhouse whitefly))、结翅白粉虱(Trialeurodes abutiloneus)(bandedwing whitefly)、尖盾蚧属种(Unaspis spp.)(蚧)、矢尖蛤(Unaspis yanonensis)(箭头蚧(arrowhead scale))和Zulia entreriana。
膜翅目(Hymenoptera)(蚂蚁、黄蜂和蜜蜂):切叶蚁属种(Acromyrrmex spp.)、新疆菜叶蜂(Athalia rosae)、叶蚁属种(Atta spp.)(Ieafcutting ants)、黑蚁属种(Camponotus spp.)(木蚁(carpenter ant))、松叶蜂属种(Diprion spp.)(叶蜂(sawfly))、蚁属种(Formica spp.)(蚂蚁)、阿根廷蚁(Iridomyrmex humilis)(Argentineant)、厨蚁属亚种(Monomorium ssp.)、小家蚁(Monomorium minumum)(littleblack ant)、厨蚁(Monomorium pharaonis)(法老蚁(Pharaoh ant))、新松叶蜂属种(Neodiprion spp.)(叶蜂)、收获蚁属种(Pogonomyrmex spp.)(收获蚁)、马蜂属种(Polistes spp.)(胡蜂(paper wasp))、火蚁属种(Solenopsis spp.)(火蚁)、香家蚁(Tapoinoma sessile)(香家蚁(odorous house ant))、铺道蚁属种(Tetranomorium spp.)(铺道蚁(pavement ant))、黄胡蜂属种(Vespula spp.)(小黄蜂(yellow jacket))和木蜂属种(Xylocopa spp.)(木蜂(carpenter bee))。
等翅目(Isoptera)(白蚁):乳白蚁属种(Coptotcrmcs spp.)、曲颚白蚁(Coptotermes curvignathus)、法国白蚁(Coptotermes frenchii)、家白蚁(Coptotermesformosanus)(Formosan subterranean termite)、角白蚁属种(Cornitermes spp.)(长鼻白蚁(nasute termite))、砂白蚁属种(Cryptotermes spp.)(干木白蚁)、异白蚁属种(Heterotermes spp.)(沙漠土栖白蚁(desert subterranean termite))、金黄异白蚁((IIeterotermes aureus)、木白蚁属种(Kalotermes spp.)(干木白蚁)、楹白蚁属种(Incistitermes spp.)(干木白蚁)、大白蚁属种(Macrotermes spp.)(培菌白蚁(fungusgrowing termite))、缘木白蚁属种((Marginitermes spp.)(干木白蚁)、锯白蚁属种(Microcerotermes spp.)(草白蚁(harvester termite))、稻麦小白蚁(Microtermesobesi)、原角白蚁属种(Procornitermes spp.)、散白蚁属种(Reticulitermes spp.)(土栖白蚁)、Reticulitermes banyulensis、草地散白蚁(Reticulitermes grassei)、黄肢散白蚁(Reticulitermes flavipes)(东方土栖白蚁)、美小黄散白蚁(Reticulitermeshageni)、西方散白蚁(Reticulitermes hesperus)(西方土栖白蚁)、桑特散白蚁(Reticulitermes santonensis)、栖北散白蚁(Reticulitermes speratus)、美黑胫散白蚁(Reticulitermes tibialis)、美小黑散白蚁(Reticulitermes virginicus)、长鼻散白蚁属种(Schedorhinotermes spp.)和古白蚁属种(Zootermopsis spp.)(腐木白蚁)。
鳞翅目(Lepidoptera)(蛾和蝶):Achoea janata,褐带卷蛾属种(Adoxophyesspp.)、棉褐带卷蛾(Adoxophyes orana)、地虎属种(Agrotis spp.)(切根虫)、小地蚕((Agrotis ipsilon)(黑切根虫)、棉叶波纹夜蛾(Alabama argillacea)(棉叶虫(cottonleafworm))、Amorbia cuneana,Amyelosis transitella(navel orangeworm)、Anacamptodes defectaria、棉条麦蛾(Anarsia lineatella)(peach twig borer)、黄麻桥夜峨(Anomis sabulijera)(jute looper)、黎豆夜蛾(Anticarsia gemmatalis)(velvetbean caterpillar)、果树卷叶蛾(Archips argyrospila)(fruit treeleafroller)、蔷薇卷叶蛾(Archips rosana)(rose leaf roller)、卷蛾属种(Argyrotaenia spp.)(tortricid moths)、桔带卷蛾(Argyrotaenia citrana)(柑桔卷叶蛾(orange tortrix))、Autographa gamma、Bonagota cranaodcs、稻纵卷叶螟(Borbocinnara)(rice leaf folder)、棉叶潜蛾(Bucculatrix thurberiella)(cottonleafperforator)、细蛾属种(Caloptilia spp.)(潜叶蛾)、Capua reticulana、桃蛀果蛾(Carposina niponensis)(桃果蛾(peach fruit moth))、禾草螟属种(Chilo spp.)、芒果横线尾夜蛾(Chlumetia transversa)(mango shoot borer)、玫瑰色卷蛾(Choristoneurarosaceana)(oblique banded leaf roller)、夜蛾属种(Chrysodeixis spp.)、稻纵卷叶野螟(Cnaphalocerus medinalis)(草地卷叶蛾(grass leafroller))、豆粉蝶属种(Coliasspp.)、荔枝爻纹细蛾(Conpomorpha cramerella)、芳香木蠢蛾(Cossus cossus)(木蠢蛾)、草螟属种(Crambus spp.)(Sod webworms)、李小食心虫(Cydia funebrana)(李果蛾(plumfruit moth))、梨小食心虫(Cydia molesta)(东方食心虫(oriental fruit moth))、豌豆蛀荚峨(Cydia nignicana)(pea moth)、苹果蠢蛾(Cydia pomonella)(苹果小卷蛾(codling moth)),Darna diducta、绢野螟属种(Diaphania spp.)(蛀茎虫(stem borer)),螟属种(Diatr aea spp.)(蛀茎虫(stalk bor er))、小蔗螟(Diatraea saccharalis)(sugarcane borer)、西南玉米杆草螟(Diatraea graniosella)(southwester cornborer)、金刚钻属种(Earias spp.)(棉铃虫)、埃及金刚钻(Earias insulata)(Egyptianbollworm)、翠纹金刚钻(Earias vit.ella)(rough northern bollworm)、Ecdytopophaaurantianum、南美玉米苗斑螟(Elasmopalpus lignosellus)(lesser cornstalk borer)、浅褐苹果蛾(Epiphysias postruttana)(light brown apple moth)、粉斑螟属种(Ephestia spp.)(粉螟)、粉斑螟(Ephestia cautella)(almond moth)、烟草粉斑螟(Ephestia elutella)(烟草螟(tobbaco moth))、地中海粉螟(Ephestia kuehniella)(Mediterranean flour moth)、Epimeces属种(Epimeces spp.)、夜小卷蛾(Epinotiaaporema)、香蕉弄蝶(Erionota thrax)(banana skipper)、女贞细卷蛾(Eupoeciliaambiguella)(葡萄浆果蛾(grape berry moth))、原切根虫(Euxoa auxiliaris)(armycutworm)、地老虎属种(Feltia spp.)(切根虫)、角剑夜蛾属种(Gortyna spp.)(蛀茎虫)、东方蛀果蛾(Grapholita molesta)(桃(杏)子食心虫(oriental fruit moth))、三纹螟蛾(Hedylepta indicata)(豆卷叶螟(bean leaf webber))、青虫属种(Helicoverpa spp.)(夜蛾)、棉铃虫(Helicoverpa armigera)(cotton bollworm)、谷实夜蛾(Helicoverpazea)(玉米螟岭(螟岭虫/棉铃虫))、实夜蛾属种(Heliothis spp.)(夜蛾)、烟芽夜蛾(Heliothis virescens)(tobacco budworm)、菜心野螟(Hellula undalis)(cabbagewebworm)、Indarbela属种(Indarbela spp.)(根蛀虫)、番茄蠢蛾(Keiferialycopersicella)(tomato pinworm)、茄白翅野螟(Leucinodes orbonalis)(eggplantfruit borer)、旋纹潜蛾(Leucoptera malifoliella)、细蛾属种(Lithocollectis spp.),葡萄小卷叶蛾(Lobesia botrana)(grape fruit moth)、Loxagrotis属种(Loxagrotisspp.)(夜蛾)、豆白线切根虫(Loxagrotis albicosta)(western bean cutworm)、舞毒蛾(Lymantria dispar)(gypsy moth)、桃潜蛾(Lyonetiaclerkella)(苹果潜叶蛾(appleleafminer))、油棕榈袋蛾(Mahasena corbetti)(oil palm bagworm)、天幕毛虫属种(Malacosoma spp.)(tent caterpillars)、甘蓝夜蛾(Mamestra brassicae)(菜行军蛾(cabbage armyworm))、豆荚野螟(Maruca testulalis)(豆野螟)、袋蛾(Metisa plana)(结草虫)、Mythimna unipuncta(true armyworm)、Neoleucinodes elegantalis(小番茄蛀虫(small tomato borer))、三点水螟(Nymphula depunctalis)(稻纵卷叶螟(ricecaseworm))、冬尺蠖(Operophthera brumata)(winter moth)、欧洲玉米螟(Ostrinianubilalis)(欧洲玉米螟(European corn borer))、Oxydia vesulia、疆褐卷蛾(Pandemiscerasana)(普通葡萄卷叶蛾(common currant tortrix))、苹褐卷蛾(Pandemis heparana)(brown apple tortrix)、非洲达摩凤蝶(Papilio demodocus)、红铃麦蛾(Pectinophoragossypiella)(红铃虫(pink bollworm))、疆夜蛾属种(Peridroma spp.)(切根虫)、杂色地老虎(Peridroma saucia)(variegated cutworm)、咖啡潜叶蛾(Perileucopteracoffeella)(white coffee leafminer)、马铃薯块茎蛾(Phthorimaea operculella)(potato tuber moth)、柑桔叶潜蛾(Phyllocnisitis citrella)、细蛾属种(Phyllonorycter spp.)(潜叶蛾)、菜粉蝶(Pieris rapae)(外来菜青虫(importedcabbageworm))、首藉绿夜蛾(Plathypena scabra)、印度谷斑蛾(Plodia interpunctella)(Indian meal moth)、菜蛾(Plutella xylostella)(diamondback moth)、葡萄浆果蛾(Polychrosis viteana)(grape berry moth)、桔果巢蛾(Prays endocarps)、油橄榄巢蛾(Prsys oleae)(olive moth)、粘虫属种(Pseudaletia spp.)(夜蛾)、Pseudaletiaunipunctata(行军虫)、大豆夜蛾(Pseudoplusia includens)(soybean looper)、尺蠖(Rachiplusia nu)、三化螟(Scirpophaga incertulas)、蛀茎夜峨属种(Sesamia spp.)(蛀茎虫)、稻蛀茎夜蛾(Sesamia inferens)(pink rice stemborer)、粉茎螟(Sesamianonagrioides)、铜斑褐刺蛾(Setora nitens)、麦蛾(Sitotroga cerealella)(Angoumoisgrain moth)、葡萄长须卷蛾(Sparganothis pilleriana)、灰翅夜蛾属种(Spodopteraspp.)(行军虫)、甜菜夜蛾(Spodoptera exigua)(甜菜行军虫(beet armyworm))、草地贪夜蛾(Spodoptcra fugipcrda)(秋季行军虫(fall armyworm))、南方灰翅夜蛾(Spodopteraoridania)(南方行军虫(southern armyworm))、兴透夜蛾属种(Synanthedon spp.)(根蛀虫)、Thecla basilides、Thermisia gemmatalis、衣蛾(Tineola bisselliella)(webbingclothes moth)、粉斑夜蛾(Trichoplusia ni)(cabbage looper)、番茄斑潜蝇(Tutsabsoluta)、巢蛾属种(Yponomeuta spp.)、咖啡豹蠢蛾(Zeuzeracoffeae)(red branchborer)和Zeuzera pyrina(梨豹蠢蛾(leopard moth))。
食毛目((Mallophaga)羽虱(chewing lice)):羊羽虱(Bovicola ovis)(sheepbiting louse)、火鸡短角羽虱(Menacanthus stramineus)(雏鸡羽虱(chicken bodylouse))和鸡羽虱(Menopon gallinea)(普通鸡舍(common hen house))。
直翅目(Orthoptera)(蚱蜢、蝗虫和蟋蟀):黑斑阿纳螽(Anabrus simplex)(摩门螽斯(Mormon cricket))、蝼蛄(Gryllotalpidae)(蝼蛄(mole cricket))、东亚飞蝗(Locusta migratoria)、蚱蜢属种(Melanoplus spp.)(蚱蜢)、纲翅细刺螽(Microcentrumretinerve)(角翅螽斯(angular winged katydid))、Pterophylla属种(Pterophyllaspp.)(螽斯)、chistocerca gregaria、叉尾螽斯(Scudderia furcata)(叉尾灌丛树螽(fork tailed bush katydid))和黑角隆脊蝗(Valanga nigricorni)。
虱目(Phthiraptera)(吸吮虱(sucking louse)):吸血虱属种(Haematopinusspp.)(牛虱和猪虱)、绵羊颚虱(Linognathus ovillus)(羊虱(sheep louse))、头虱(Pediculus humanus capitis)(体虱)、人体虱(Pediculus humanus humanus)(体虱)和阴虱(Pthirus pubis)(阴虱(crab louse))。蚤目(Siphonaptera)(跳蚤):犬栉首蚤(Ctenocephal ides canis)(dog flea)、猫栉首蚤(Ctenocephalides felis)(cat flea)和人蚤(Pulex irritans)(human flea)。
缨翅目(蓟马):烟褐蓟马(Frankliniella fusca)(tobacco thrip)、西方花蓟马(Frankliniella occidentalis)(western flower thrips)、Frankliniella shultzei、威廉斯花蓟马(Frankliniella williamsi)(玉米蓟马(corn thrip))、温室蓟马(IIeliothrips haemorrhaidalis)(greenhouse thrip)、Riphiphorothrips cruentatus、硬蓟马属种(Scirtothrips spp)、桔梗蓟马(Scirtothrips cirri)(citrus thrip)、茶黄蓟马(Scirtothrips dorsalis)(yellow tea thrips)、Taeniothrips rhopalantennalis和蓟马属种(Thrips spp.)。
缨尾目(Thysanura)(蛀虫(bristletail)):衣鱼属种(Lepisma spp.)(蠢虫(silverfish))和小灶衣鱼属种(Thermobia spp.)(小灶鱼)。
螨目(Acarina)(螨(mite)和蝉(tick)):伍氏蜂盾螨(Acarapsis woodi)(蜜蜂气管内寄生螨(tracheal mite of honeybee))、粉螨属种(Acarus spp.)(食物螨)、粗脚粉螨(Acarus siro)(谷螨(grain mite))、芒果芽螨(Aceria mangiferae)(mango bud mite)、刺皮瘿螨属种(Aculops spp.)、番茄刺皮瘿螨(Aculops lycopersici)(tomato russetmite)、Aculops pelekasi、桔刺皮瘿螨(Aculus pelekassi)、斯氏刺瘿螨(Aculusschlechtendali)(苹刺瘿螨(apple rust mite))、美洲花蜱(Amblyomma amcricanum)(lone star tick)、牛蜱属种(Boophilus spp.)(蜱)、卵形短须蜱(Brevipalpusobovatus)(privet mite)、紫红短须螨(Brevipalpus phoenicis)(red and black flatmite)、脂蜱属种(Demodex spp.)(mange mites)、革蜱属种(Dermacentorspp.)(硬蜱)、美洲狗蜱(Dermacentor variabilis)(american dog tick)、屋尘螨(Dermatophagoidespteronyssinus)(house dust mite)、始叶螨属种(Eotetranycus spp.)、鹅耳枥始叶螨(Eotetranychus carpini)(黄蜘蛛螨(yellow spider mite))、上瘿螨属种(Epitimerusspp.)、瘿螨属种(Eriophyes spp.)、硬蜱属种(工;odes spp.)(蜱)、全爪螨属种((Metatetranycus spp.)、猫耳螨(Notoedres cati)、小爪螨属种(Oligonychus spp.)、咖啡小爪螨(Oligonychus coffee)、冬青小爪螨(Oligonychus ilicus)(southernred mite)、全爪螨属种(Panonychus spp.)、桔全爪螨(Panonychus cirri)(桔红蜘蛛(citrusred mite))、苹果全爪螨(Panonychus ulmi)(欧洲红蜘蛛(European red mite))、桔皱叶刺瘿(Phyllocoptruta oleivora)(citrus rust mite)、侧多食跗线螨(Polyphagotarsonemun latus)(广明螨(broad mite))、血红扇头蜱(Rhipicephalussanguineus)(褐狗蜱(brown dog tick))、根螨属种(Rhizoglyphus spp.)(根螨(bulbmite))、疥螨(Sarcoptes scabiei)(itch mite)、鳄梨顶冠瘿螨(Tegolophusperseaflorae)、叶螨属种(Tetranychus spp.)、二点叶螨(Tetranychus urticae)(二点蜘蛛螨(twospotted spider mite))和狄氏瓦螨(Varroa destructor)(蜜蜂螨)。
线虫纲(线虫):滑刃线虫属种(Aphelenchoides spp.)(芽和叶以及松材线虫(budand leaf&pine wood nematode))、刺线虫属种(Belonolaimus spp.)(sting nematodes)、小环线虫属种(Criconemella spp.)(ring nematodes)、犬恶丝虫(Dirofilaria immitis)(dog heartworm)、茎线虫属种(Ditylenchus spp.)(茎和球茎线虫)、棘皮线虫属种(Heterodera spp.)(cyst nematode)、玉米胞囊线虫(Heterodera zeae)(corn cystnematode)、潜根线虫属种(Hirschmanniella spp.)(root nematodes)、纽带线虫属种(Hoplolaimus spp.)(lance nematodes)、根结线虫属种(Meloidogyne spp.)(根结线虫)、南方根结线虫((Meloidogyne incognita)(根结线虫)、旋盘尾丝虫(Onchocercavolvulus)(hook-tail worm)、短体线虫属种(PraLylenchus spp.)(腐线虫(lesionnematode))、穿孔线虫属种(Radopholus spp.)(穿孔线虫(burrowing nematode))和香蕉肾状线虫(Rotylenchus reniformis)(kidney-shaped nematode)。
综合纲(综合虫类):白松虫(Scutigerella immaculata)。
特别地,在较低剂量下对桃蚜和朱砂叶螨仍具有很好的防治效果。
由于其积极的特性,上述化合物可有利地用于保护农业和园艺业重要的作物、家畜和种畜,以及人类常去的环境免于病菌、害虫害螨的伤害。
为获得理想效果,化合物的用量因各种因素而改变,例如所用化合物、预保护的作物、有害生物的类型、感染程度、气候条件、施药方法、采用的剂型。
每公顷10克-5公斤的化合物剂量能提供充分的防治。
本发明还包括以通式I化合物作为活性组分的杀菌、杀虫杀螨组合物。该杀菌、杀虫杀螨组合物中活性组分的重量百分含量在0.5-99%之间。该杀菌、杀虫杀螨组合物中还包括农业、林业、卫生上可接受的载体。
本发明的组合物可以制剂的形式施用。通式I化合物作为活性组分溶解或分散于载体中或配制成制剂以便作为杀菌、杀虫使用时更易于分散。例如:这些化学制剂可被制成可湿性粉剂、油悬剂、水悬剂、水乳剂、水剂或乳油等。在这些组合物中,至少加入一种液体或固体载体,并且当需要时可以加入适当的表面活性剂。
本发明的技术方案还包括防治病菌、害虫害螨的方法:将本发明的杀菌、杀虫杀螨组合物施于所述的病菌或其生长介质上。通常选择的较为适宜有效量为每公顷10克到1000克,优选有效量为每公顷20克到500克。
对于某些应用,例如在农业上可在本发明的杀菌、杀虫杀螨组合物中加入一种或多种其它的杀菌剂、杀虫杀螨剂、除草剂、植物生长调节剂或肥料等,由此可产生附加的优点和效果。
应明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非仅限于这些例子(除另有注明外,所用原料均有市售)。
合成实施例
实施例1:中间体4,5-二氯-6-甲基嘧啶的制备
1)4-羟基-5-氯-6-甲基嘧啶的制备
室温搅拌下向11.30g(0.11mol)醋酸甲脒的50ml甲醇溶液中缓慢滴加8.80g(0.16mol)甲醇钠的甲醇溶液,滴毕室温继续搅拌2h。然后向上述溶液中滴加11.17g(0.068mol)中间体2-氯乙酰乙酸乙酯,继续室温搅拌反应5-7小时。TLC监测反应完毕后,减压蒸除溶剂,用盐酸调pH=5~6,抽滤得橙黄色固体,水相用(3×50ml)乙酸乙酯萃取,无水硫酸镁干燥、过滤、脱溶。残余物溶于50ml乙酸乙酯中,放置过夜,过滤得橙黄色固体6.48g。收率66%,熔点181~184℃。
2)4,5-二氯-6-甲基嘧啶的制备
将14.5g(0.1mol)4-羟基-5-氯-6-甲基嘧啶溶于50ml甲苯溶液中,搅拌下向反应瓶中滴入50ml三氯氧磷,滴毕升温回流反应5-7小时。TLC监测反应完毕后,减压蒸除甲苯和过量的三氯氧磷,搅拌下将反应物倾入冰水中,水相用(3×50ml)乙酸乙酯萃取,合并有机相,无水硫酸镁干燥、过滤、脱溶。残余物柱层析(洗脱剂为乙酸乙酯与石油醚,体积比为1:5)分离得黄色液体14.43g,收率88.5%。
实施例2:4,5-二氯噻吩并[2,3-d]嘧啶的制备
取2-氨基-3-氰基-4-氧代-5,5-二氢噻吩和250ml三氯氧磷(POCl3)于反应瓶中,室温下慢慢滴加38ml N,N-二甲基甲酰胺,约30分钟滴加完毕。室温反应1小时,再升温至75℃反应3小时。降至室温后,将反应液倒入碎冰中,过滤得深灰色固体89.1g,收率86.9%,熔点160-161℃。
实施例3:中间体4-氯喹唑啉的制备
1)喹唑啉-4(3H)-酮的制备
取13.7g(0.1mol)邻氨基苯甲酸与20ml甲酰胺于250ml三口瓶中,升温至140℃反应5-8小时。TLC监测反应完毕后,将反应液降温至100℃,搅拌下滴加80ml水,之后冷却至室温,过滤并用用无水乙醚洗涤滤饼得红棕色10.96g,收率75.1%。
2)4-氯喹唑啉的制备
取14.6g(0.1mol)喹唑啉-4(3H)-酮于250ml单口瓶中,50ml氯化亚砜作溶剂,升温至回流反应4-6小时。TLC监测反应完毕后,冷却后将反应液倒入水中搅拌30min,过滤并用无水乙醚洗涤得红棕色固体10.96g,收率92.7%。
实施例4:中间体2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺盐酸盐的合成
1)N-Boc-2-溴乙胺的制备
将20.5g(0.1mol)溴乙胺溴酸盐置于80ml四氢呋喃中,依次加入10.08g(0.12mol)碳酸氢钠、50ml水,室温搅拌下滴加21.80g(0.1mol)二碳酸二叔丁酯,滴毕,继续反应4-10小时。反应完毕后,减压蒸除溶剂,加入(3×50ml)乙酸乙酯萃取,有机相用饱和食盐水50ml洗涤,脱溶后得无色油状液体21.84g,收率97.5%。
2)N-Boc-2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺的制备
将2.24g(0.01mol)N-Boc-2-溴乙胺与1.61g(0.01mol)1-苯基-1H-1,2,4-三唑-3-醇加入50ml DMF中,加入2.76g(0.02mol)碳酸钾,搅拌下加热至回流,反应4-10小时,TLC监测反应完毕后,减压蒸除溶剂,加入(3×50ml)乙酸乙酯萃取,有机相用饱和食盐水50ml洗涤,脱溶后残余物柱层析(洗脱剂为乙酸乙酯与石油醚,体积比为1:6)得白色固体2.28g,收率75.1%。
3)2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺盐酸盐的制备
将3.04g(0.01mol)N-Boc-2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺加入50ml乙酸乙酯中,室温搅拌下滴加6ml浓盐酸,固体溶解,继续搅拌4-5小时,TLC监测反应完毕后,减压蒸除溶剂,加入10ml二氯甲烷搅拌半小时,过滤,并用二氯甲烷洗涤滤饼得1.75g白色固体。
实施例5:化合物35-1的制备
将1.77g(0.01mol)4,5-二氯-6-乙基嘧啶和2.4g(0.01mol)2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺盐酸盐加入50ml甲苯中。加入4.45g(0.022mol)三乙胺,加热至回流,反应4-10小时,TLC监测反应完毕后,减压蒸除溶剂,加入(3×50ml)乙酸乙酯萃取,有机相用饱和食盐水50ml洗涤,脱溶后残余物柱层析(洗脱剂为乙酸乙酯与石油醚(沸程60-90℃),体积比为1:4)得白色固体2.58g,收率75%,熔点157.0℃。
1H-NMR(300MHz,内标TMS,溶剂CDCl3)δ(ppm):8.43(s,Triazole-1H),8.26(s,Pyrimidine-1H),7.60(d,J=8.1Hz,Ph-2,6-2H),7.50-7.33(m,Ph-3,4,5-3H),5.60(s,1H,NH),4.58(t,J=4.8Hz,2H,O-CH2),3.99(q,J=5.1Hz,2H,N-CH2),2.77(q,J=7.2Hz,2H,CH2),1.25(t,J=7.2Hz,3H,CH3)
实施例6:化合物43-1的制备
将1.64g(0.01mol)4-氯喹唑啉和2.4g(0.01mol)2-(1-苯基-1H-1,2,4-三唑-3-氧基)乙胺盐酸盐加入50ml甲苯中。加入4.45g(0.022mol)三乙胺,加热至回流,反应4-10小时,TLC监测反应完毕后,减压蒸除溶剂,加入(3×50ml)乙酸乙酯萃取,有机相用饱和食盐水50ml洗涤,脱溶后残余物柱层析(洗脱剂为乙酸乙酯与石油醚(沸程60-90℃),体积比为1:4)得2.59g黄色油状物,收率78.1%。
1H-NMR(300MHz,内标TMS,溶剂CDCl3)δ(ppm):8.91(s,Triazole-1H),8.50(s,Pyrimidine-1H),8.44(s,1H,NH),8.24(d,J=8.1Hz,Ph-2,6-2H),7.74-7.67(m,Ph-4H),7.49-7.44(m,Ph-3,4,5-3H),4.55(t,J=5.4Hz,2H,O-CH2),3.97(q,J=5.7Hz,2H,N-CH2)
本发明的其他化合物可以参照以上实施例制备。
部分化合物的物性数据及核磁数据(1HNMR,300MHz,内标TMS,ppm)如下:
化合物36-1:熔点138.2℃。δ(CDCl3)8.56(s,Triazole-1H),8.26(s,Pyrimidine-1H),7.61(d,J=8.4Hz,Ph-2,6-2H),7.51-7.34(m,Ph-3,4,5-3H),6.70(s,1H,CHF2),4.61(t,J=5.1Hz,2H,O-CH2),4.03(q,J=5.1Hz,2H,N-CH2)。
化合物45-1:熔点123.6℃。δ(CDCl3)8.48(s,Triazole-1H),8.25(s,Pyrimidine-1H),7.58(d,J=8.7Hz,Ph-2,6-2H),7.49-7.35(m,Ph-3,4,5-3H),7.04(s,Thiophene-1H),4.64(t,J=5.1Hz,2H,O-CH2),4.12(q,J=5.1Hz,2H,N-CH2)。
化合物67-1:熔点120.6℃。δ(CDCl3)8.27(s,2H),7.62(d,J=8.1Hz,Ph-2,6-2H),7.52-7.35(m,Ph-3,4,5-3H),6.26(s,1H,NH),4.51(t,J=5.4Hz,2H,O-CH2),3.76(q,J=6.0Hz,2H,N-CH2),2.17(m,2H,CH2)。
化合物68-1:δ(CDCl3)8.27(s,Triazole-1H),8.05(s,Pyrimidine-1H),7.59(d,J=7.8Hz,Ph-2,6-2H),7.51-7.35(m,Ph-3,4,5-3H),5.73(s,1H,NH),4.54(t,J=5.7Hz,2H,O-CH2),3.74(q,J=6.3Hz,2H,N-CH2),2.17(m,2H,CH2)。
化合物69-1:δ(CDCl3)9.53(s,Triazole-1H),8.28(s,Pyrimidine-1H),7.62(d,J=7.5Hz,Ph-2,6-2H),7.55-7.35(m,Ph-3,4,5-3H),4.47(t,J=5.4Hz,2H,O-CH2),3.85(q,J=6.6Hz,2H,N-CH2),2.21(m,2H,CH2)。
化合物71-1:熔点135℃。δ(CDCl3)8.27(s,1H),7.61(d,J=8.4Hz,Ph-2,6-2H),7.52-7.38(m,Ph-3,4,5-3H),4.53(t,J=5.4Hz,2H,O-CH2),3.73(q,J=6.0Hz,2H,N-CH2),2.18(m,5H)。
化合物72-1:δ(CDCl3)8.28(s,Triazole-1H),8.14(s,Pyrimidine-1H),7.61(d,J=8.1Hz,Ph-2,6-2H),7.51-7.36(m,Ph-3,4,5-3H),6.06(s,1H,NH),4.50(t,J=5.7Hz,2H,O-CH2),3.99(s,3H),3.72(q,J=6.3Hz,2H,N-CH2),2.18(m,2H,CH2)。
化合物73-1:熔点102.1℃。δ(CDCl3)8.36(s,Triazole-1H),8.26(s,Pyrimidine-1H),7.62(d,J=8.1Hz,Ph-2,6-2H),7.51-7.34(m,Ph-3,4,5-3H),5.90(s,1H,NH),4.50(t,J=5.7Hz,2H,O-CH2),3.74(q,J=6.3Hz,2H,N-CH2),2.18(m,2H,CH2),2.45(s,3H,CH3)。
化合物74-1:熔点149.5℃。δ(CDCl3)8.41(s,Triazole-1H),8.26(s,Pyrimidine-1H),7.62(d,J=8.1Hz,Ph-2,6-2H),7.51-7.34(m,Ph-3,4,5-3H),5.91(s,1H,NH),4.51(t,J=6.0Hz,2H,O-CH2),3.74(q,J=6.3Hz,2H,N-CH2),2.78(q,J=7.5Hz,2H,CH2),2.18(m,2H,CH2),1.26(t,J=7.8Hz,3H,CH3)。
化合物75-1:熔点118.9℃。δ(CDCl3)8.53(s,Triazole-1H),8.26(s,Pyrimidine-1H),7.61(d,J=8.1Hz,Ph-2,6-2H),7.51-7.34(m,Ph-3,4,5-3H),6.72(s,1H,CHF2),6.32(s,1H,NH),4.52(t,J=5.7Hz,2H,O-CH2),3.80(q,J=6.3Hz,2H,N-CH2),2.19(m,2H,CH2)。
化合物76-1:熔点130.6℃。δ(CDCl3)8.65(s,Triazole-1H),8.28(s,Pyrimidine-1H),7.84-7.60(m,4H),7.52-7.36(m,5H),6.64(s,1H,NH),4.60(t,J=5.4Hz,2H,O-CH2),3.91(q,J=5.7Hz,2H,N-CH2),2.27(m,2H,CH2)。
化合物76-2-1:熔点210.5℃。δ(CDCl3):8.92(s,Triazole-1H),8.51(s,Pyrimidine-1H),8.40(s,Ph-1H),7.80-7.72(m,Ph-3H),7.57(d,J=8.7Hz,Ph-1H),7.49-7.31(m,Ph-3H),4.40(t,J=6.0Hz,2H,O-CH2),3.69(q,J=6.2Hz,2H,N-CH2),2.16(m,2H,CH2)。
化合物77-1:熔点111.7℃。δ(CDCl3)8.45(s,Triazole-1H),8.25(s,Pyrimidine-1H),7.61(d,J=8.4Hz,Ph-2,6-2H),7.50-7.33(m,Ph-3,4,5-3H),7.05(s,Thiophene-1H),6.98(s,1H,NH),4.55(t,J=6.0Hz,2H,O-CH2),3.88(q,J=6.0Hz,2H,N-CH2),2.25(m,2H,CH2)。
生物活性测定实施例
本发明化合物对农业领域中的多种病菌、害虫害螨都表现出很好的活性。
实施例8:杀菌活性测定
用本发明化合物样品对植物的多种真菌病害进行了离体抑菌活性或活体保护效果试验。杀菌活性测定结果见以下各实施例。
(1)离体杀菌活性测定
测定方法如下:采用高通量筛选方法,即将待测化合物样品用适合的溶剂(溶剂的种类如丙酮、甲醇、DMF等,并且依据其对样品的溶解能力而选择)溶解,配制成所需浓度待测液。在超净工作环境下,将待测液加入到96孔培养板的微孔中,再将病原菌繁殖体悬浮液加入其中,处理后的培养板放置在恒温培养箱中培养。24小时后进行调查,调查时目测病原菌繁殖体萌发或生长情况,并根据对照处理的萌发或生长情况,评价化合物抑菌活性。
部分化合物的离体抑菌活性(以抑制率表示)测试结果如下:
对稻瘟病菌的抑制率:
在25ppm剂量下,化合物35-1和77-1对稻瘟病的抑制率为100%;在8.3ppm剂量下,化合物35-1、77-1对稻瘟病的抑制率在80%以上。
(2)活体保护活性测定
测定方法如下:采用活体盆栽测定方法,即将待测化合物样品用少量溶剂(溶剂的种类如丙酮、甲醇、DMF等,并且依据其对样品的溶解能力而选择,溶剂量与喷液量的体积比等于或小于0.05)溶解,用含有0.1%吐温80的水稀释,配制成所需浓度待测液。在作物喷雾机上,将待测液喷施于病害寄主植物上(寄主植物为在温室内培养的标准盆栽苗),24小时后进行病害接种。依据病害特点,将需要控温保湿培养的病害植物接种后放在人工气候室中培养,待病害完成侵染后,移入温室培养,将不需要保湿培养的病害植物直接在温室内接种并培养。待对照充分发病后(通常为一周时间)进行化合物防病效果评估。
部分化合物的活体保护活性测试结果如下:
对黄瓜霜霉病的活体保护活性:
在400ppm剂量下,化合物35-1、36-1、43-1、45-1、73-1、74-1、75-1、76-1、77-1等化合物对黄瓜霜霉病防效在80%以上,其中化合物36-1、43-1、45-1、73-1、74-1、75-1、76-1、77-1的防效接近100%;在100ppm剂量下,化合物75-1、77-1对黄瓜霜霉病防效在80%以上。
对小麦白粉病的活体保护活性:
在400ppm剂量下,化合物75-1、76-1等对小麦白粉病的防效接近100%。
对玉米锈病的活体保护活性:
在400ppm剂量下,化合物35-1、74-1、75-1、76-1、77-1等对玉米锈病防效在80%以上,其中化合物74-1、75-1、76-1、77-1对玉米锈病的防效接近100%;在100ppm剂量下,化合物74-1对玉米锈病的防效大于80%。
对黄瓜炭疽病的活体保护活性:
在400ppm剂量下,化合物75-1、76-1、77-1等对黄瓜炭疽病防效在80%以上;在100ppm剂量下,化合物75-1对黄瓜炭疽病的防效大于80%。
实施例9:杀虫杀螨活性测定
用本发明化合物对几种昆虫进行了杀虫活性测定试验。测定方法如下:
待测化合物用丙酮/甲醇(1:1)的混合溶剂溶解后,用含有0.1%(wt)吐温80的水稀释至所需的浓度。
以桃蚜、朱砂叶螨为靶标,采用airbrush喷雾法进行杀虫活性测定。
(1)杀桃蚜的活性测定
测定方法:取直径6cm培养皿,皿底覆一层滤纸,并滴加适量自来水保湿。从培养桃蚜的甘蓝植株上剪取大小适宜(直径约3cm)且长有15~30头蚜虫的甘蓝叶片,去除有翅蚜及叶片正面的蚜虫,叶背向上置于培养皿内。airbrush喷雾处理的压力为10psi(约合0.7kg/cm2),喷液量为0.5ml,每处理3次重复。处理后放入25℃、相对湿度60~70%观察室内培养,48小时后调查存活虫数,计算死亡率。
在600ppm剂量下,化合物74-1、75-1、76-2-1等对桃蚜的致死率在80%以上;其中化合物74-1、75-1对桃蚜的致死率接近100%。
(2)杀朱砂叶螨的活性测定
测定方法:取两片真叶菜豆苗,接上朱砂叶螨成螨并调查基数后,用airbrush喷雾器进行整株处理,压力为10psi(约合0.7kg/cm2),喷液量为0.5ml。每处理3次重复,处理后置于标准观察室,72小时后调查存活螨数,计算死亡率。
对朱砂叶螨的部分测试结果如下:
在600ppm剂量下,化合物74-1、76-2-1等对朱砂叶螨的致死率在80%以上。
Claims (5)
1.一种含嘧啶的取代唑类化合物,其特征在于:化合物如通式IC和IO所示:
R1选自氢、卤素、C1-C12烷基、卤代C1-C12烷基;
R2选自氢、卤素、硝基、氨基、C1-C12烷基、卤代C1-C12烷基、C1-C12烷氧基或卤代C1-C12烷氧基;
R1和R2与相连的嘧啶环组成含C或S的五元或六元环;
R3选自氢;
R4、R5分别选自氢;
R6、R7分别选自氢;
R8选自氢;
R10选自氢;
W选自氢;
或通式IC和IO所示化合物的盐。
2.根据权利要求1所述的含嘧啶的取代唑类化合物,其特征在于:通式IC和IO中
R1选自氢、氯、甲基、乙基或二氟甲基;
R2选自氢、氯、溴、硝基、氨基、甲基或甲氧基;
R1和R2与相连的嘧啶环组成含C或S的五元或六元环;
R3选自氢;
R4、R5分别选自氢;
R6、R7均选自氢;
R8选自氢;
W选自氢;
或通式IC和IO化合物与盐酸、硫酸、磷酸、甲酸、乙酸、三氟乙酸、草酸、甲磺酸、对甲苯磺酸、苯甲酸、邻苯二甲酸、马来酸、富马酸、山梨酸、苹果酸或柠檬酸形成的盐。
3.一种按照权利要求1-2中任意一项所述含嘧啶的取代唑类化合物在农业或其他领域中用作制备杀菌剂、杀虫杀螨剂药物的用途。
4.一种杀菌杀虫杀螨组合物,其特征在于:组合物以如权利要求1-2中任意一项所述含嘧啶的取代唑类化合物作为活性组分,组合物中活性组分的重量百分含量为0.1-99%。
5.一种按照权利要求4所述的组合物在农业或其他领域中防治病菌、害虫害螨的用途。
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