CN110475776A - 用于防治节肢动物的三环羧酰胺 - Google Patents
用于防治节肢动物的三环羧酰胺 Download PDFInfo
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- CN110475776A CN110475776A CN201880023366.7A CN201880023366A CN110475776A CN 110475776 A CN110475776 A CN 110475776A CN 201880023366 A CN201880023366 A CN 201880023366A CN 110475776 A CN110475776 A CN 110475776A
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- IHNSIFFSNUQGQN-UHFFFAOYSA-N tioxazafen Chemical compound C1=CSC(C=2ON=C(N=2)C=2C=CC=CC=2)=C1 IHNSIFFSNUQGQN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000006000 trichloroethyl group Chemical group 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- DBXFMOWZRXXBRN-LWKPJOBUSA-N valifenalate Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)NC(CC(=O)OC)C1=CC=C(Cl)C=C1 DBXFMOWZRXXBRN-LWKPJOBUSA-N 0.000 description 1
- 239000013598 vector Substances 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
- 239000012873 virucide Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-nitrogen bonds, e.g. azides, diazo-amino compounds, diazonium compounds, hydrazine derivatives
-
- C—CHEMISTRY; METALLURGY
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P7/00—Arthropodicides
- A01P7/04—Insecticides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Abstract
本发明尤其涉及通式(I)的化合物。本发明还涉及合成式(I)的化合物的方法。本发明的化合物特别适用于防治农业应用中的昆虫、蛛形纲动物和线虫以及防治兽医学中的体外寄生虫。
Description
引言
本申请涉及新的化合物、其制备方法及其用于防治动物害虫、特别是节肢动物且尤其是昆虫、蛛形纲动物和线虫的用途。
已知特定的卤素取代的化合物具有杀昆虫活性(EP 1911751、WO 2012/069366、WO2012/080376、WO2012/107434和WO2012/175474)。
WO 2011/113756公开了具有杀昆虫活性的三唑衍生物。
此外,已知某些卤素取代的化合物具有细胞因子抑制活性(WO 2000/07980)。
现代作物保护组合物必须满足许多要求,例如关于其作用程度、作用持久性和作用谱,以及可能的用途。毒性问题以及与其他活性成分或制剂助剂的结合性问题占据一席之位,在合成活性成分时所涉及的成本和复杂性问题亦是如此。此外,会产生抗性。出于所有这些原因,绝不能认为对新的作物保护剂的探寻已经完成,而是不断需要与已知化合物相比至少在个别方面具有改进的特性的新的化合物。
本发明的一个目的是提供在各方面拓宽农药谱和/或改进活性的化合物。
出乎意料地,现已发现,特定的卤素取代的化合物及其盐具有生物学特性并且尤其适用于防治动物害虫,因此其在农业化学领域和动物健康领域具有特别好的适用性。
类似的化合物已由WO 2010/051926、WO 2012/102387、WO 2012/000896、WO 2011/045224、WO 2008/074835已知。
本发明化合物的实施方案
本发明的一方面涉及新的卤素取代的化合物,其具有杀昆虫、杀螨和/或杀寄生虫活性且具有通式(I)的结构,以及式(I)的化合物的盐、N-氧化物和互变异构形式:
(I)
其中
R1 为H,任选地在每种情况下彼此独立地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰基、C1-C4-羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基(C1-C4-alkylsulfenyl)和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基(C1-C4-alkylphosphinyl)、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基(例如亚甲基或亚乙基)、氧代基取代的或亚氨基取代的C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C7-环烷基、C1-C6-烷基羰 基、C1-C6-烷氧基羰基、C6-芳基(C1-C3)-烷基、C10-芳基(C1-C3)-烷基、C14-芳基(C1-C3)-烷 基、3-元杂环基、4-元杂环基、5-元杂环基、6-元杂环基、7-元杂环基、8-元杂环基、9-元杂环 基或10-元杂环基(如硫杂环丁烷基,如硫杂环丁烷-3-基、氧化硫杂环丁烷如1-氧化硫杂环丁烷-3-基、或二氧化硫杂环丁烷如1,1-二氧化硫杂环丁烷-3-基)或3-元杂环基(C 1 -C 3 )-烷基、4-元杂环基(C 1 -C 3 )-烷基、5-元杂环基(C 1 -C 3 )-烷基、6-元杂环基(C 1 -C 3 )-烷基、7-元杂环基(C 1 -C 3 )-烷基、8-元杂环基(C1-C3)-烷基、9-元杂环基(C1-C3)-烷基或10-元杂环基(C1- C3)-烷基,
优选任选被卤素或氰基取代的C3-C7-环烷基,或
C6-芳基(C1-C3)-烷基、C10-芳基(C1-C3)-烷基、C14-芳基(C1-C3)-烷基,其中C6-芳基、C10-芳基、C14-芳基可任选地彼此独立地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基和C1-C4-烷基,或
C1-C6-烷基羰基;
更优选任选地被氰基取代的C3-环烷基(尤其是环丙基或1-CN-环丙基),或C6-芳基(C1-C3)-烷基(尤其是–CH2-C6H5);
R2 为H或任选地彼此独立地被一个或多个选自以下的取代基取代:
氨基、羟基、卤素、硝基、氰基、巯基、C1-C4-羧基、碳酰胺基、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基(如亚甲基或亚乙基)或氧代基取代的C1-C6-烷基(优选H或–CH3);
部分
A1、A2和A3各自独立地为N、O、CR3、S或N-R4,优选N、CR3、S或N-R4,其中A1、A2、A3、Z和环的碳原子形成芳族体系;
R3各自独立地为H、Cl、F、I、Br或任选卤代的C1-C4-烷基,优选甲基;
R4各自独立地为H或任选卤代的C1-C4-烷基,优选甲基;
Q为O或S,优选O;
Z为C或N;优选C;
B1和B5各自独立地为N或C-R5,并且
B2、B3和B4各自独立地为C-R5,其中
R5各自独立地为H、卤素、氰基、硝基、SF5,在每种情况下任选地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰基、C1-C4-羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基(如亚甲基或亚乙基)、氧代基取代的或亚氨基取代的C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、N-C1-C6-烷氧基亚氨基-C1-C3-烷基、C1-C6-烷基硫烷基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、N-C1-C6-烷基氨基或N,N-二-C1-C6-烷基氨基;
T为下文所示的5元杂芳族体系T1-T4和T6之一,其中与连接的键用#号表示,
本发明的一个优选的实施方案涉及根据第[0009]段的化合物,其中R2为H或甲基。
另一个优选的实施方案涉及根据第[0009]或[0010]段的化合物,其中T为T1、T2或T4,更优选T1。
另一个优选的实施方案涉及根据第[0009]至[0011]段中任一段的化合物,其中R1为任选地被氰基取代的环丙基(优选环丙基或1-CN-环丙基),或C6-芳基(C1-C3)-烷基(优选–CH2-C6H5)。R1特别优选为苄基、环丙基或1-CN-环丙基,尤其优选环丙基或1-CN-环丙基。
另一个优选的实施方案涉及根据第[0009]至[0012]段中任一段的化合物,其中Q为O。
另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中A3为S。
另一个优选的实施方案涉及根据第[0009]至[0014]段中任一段的化合物,其中A3为S,Z为C,A2为C-(任选卤代的C1-C4-烷基)(优选C-CH3)、C-H或C-Hal,其中Hal为Cl、Br或I,优选Br或Cl,且A1为C-H或N。在另一个优选的实施方案中,A3为S,Z为C,A2为C-Hal,其中Hal为Cl、Br或I,且A1为C-H。在另一个优选的实施方案中,A3为S,Z为C,A2为C-H或C-Hal,其中Hal为Cl、Br或I,优选Cl,且A1为N。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中A1为S,优选其中A1为S,A2为C-H或C-Hal,优选C-Hal,其中Hal为Cl、Br或I,优选Br或Cl,甚至更优选Cl,Z为C,且A3为C-H。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中A3为O。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0017]段中任一段的化合物,其中A3为O,Z为C,A1为C-H且A2为C-Hal,其中Hal为Cl、Br或I,优选Cl。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中A3为C-H,A1为S,Z为C且A2为C-Hal,其中Hal为Cl、Br或I,优选Cl。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中A3为C-H或C-Hal,其中Hal为Cl、Br或I,优选Cl,A2为N-H或N-(C1-C4-烷基)(优选N-(C1-C4-烷基),更优选N-CH3),A1为C-H、C-Hal,其中Hal为Cl、Br或I,优选Cl,或C-(C1-C4-烷基),更优选其中A3为C-H或C-Cl,A2为N-CH3,A1为C-H。
在这种情况下,另一个优选的实施方案涉及根据第[0009]至[0013]段中任一段的化合物,其中Z为C,A1为N,A2为S且A3为C-H。
在这种情况下,另一个优选的实施方案涉及根据第[0009]段至前述段落中任一段的化合物,其中B1和B5各自为C-H、C-CH3或C-Hal,优选C-Cl。特别优选其中B1和B5各自为C-Cl。
在这种情况下,另一个优选的实施方案涉及根据第[0009]段至前述段落中任一段的化合物,其中B2和B4各自为C-H。
在这种情况下,另一个优选的实施方案涉及根据第[0009]段至前述段落中任一段的化合物,其中B3为CR5且R5为全卤代的C1-C4-烷基,优选全氟代的C1-C4-烷基,更优选全氟代的丙基。
在这种情况下,另一个优选的实施方案涉及式(Ia)的化合物,
其中B1至B5、A1至A3、Z、R1、R2和T如本文对式(I)的化合物及其优选实施方案所定义。
在这种情况下,另一个优选的实施方案涉及式(Ib)的化合物,
其中B1至B5、A1至A3、Z、R1、R2和T如本文对式(I)的化合物及其优选实施方案所定义。
在每种情况下,另一个优选的实施方案涉及式(1c)、(1d)和(1f)至(1k)的化合物,其中如果这些式之一没有明确定义,则任选出现的符号A1至A3、B1至B5、T、Z、R1至R2各自如本文对式(I)的化合物及其优选实施方案所定义,并且“Alk”为C1-C4-烷基,“Hal”为氯或溴,且V为C1-C4-烷氧基或N(R1R2)。
在这种情况下,另一个优选的实施方案涉及式(I‘a)的化合物,
其中Q、R1、R2、A1、A2和A3如本文对式(I)的化合物及其优选实施方案所定义。
在这种情况下,另一个优选的实施方案涉及式(I‘b)的化合物,
其中A1为N或C-H且R3如本文所定义,优选C1-C4-烷基、C-H或C-Hal,其中Hal为Cl、Br或I,优选Br或Cl,尤其优选R3为CH3,另外R1和R2如本文所定义。
在这种情况下,另一个优选的实施方案涉及式(I‘c)的化合物,
其中A1为C-H且R3优选为C-Cl且另外R1和R2如本文所定义。
在这种情况下,另一个优选的实施方案涉及式(I‘d)的化合物,
其中如果A2为N-(卤代的C1-C4-烷基)或N-(C1-C4-烷基),则A1为C-R3,优选C-H;或如果A2为S,则A1为N且另外R1和R2如本文所定义。
在式(I‘a)、(I‘b)、(I‘c)和(I‘d)之一中,R2优选为H或CH3且R1为任选地被CN取代的环丙基(如环丙基或1-CN-环丙基)。
另一方面涉及杀昆虫组合物,其包含至少一种根据第[0009]段至前述段落中任一段的式(I)或由式(I)衍生的式的化合物以及增量剂和/或表面活性物质。
另一方面涉及一种保护转基因或常规种子和由其生长的植物免受害虫侵害的方法,其特征在于,使用至少一种根据第[0009]至[0032]段中任一段的化合物处理种子。
另一方面涉及根据第[0009]至[0032]段中任一段的化合物或根据第[0033]段的杀昆虫组合物用于防治害虫的用途。
另一方面涉及种子,其中将第[0009]至[0032]段中任一段的化合物作为包衣成分或作为除包衣之外的另一层或另几层施用于种子。
另一方面涉及一种保护转基因或常规种子和由其生长的植物免受害虫侵害的方法,其特征在于,使用至少一种如本文所述的式(I)或由式(I)衍生的式的化合物处理种子。
又一方面涉及如本文所述的式(I)或由式(I)衍生的式的化合物或如本文所述的杀昆虫组合物用于防治害虫的用途。
又一方面涉及如本文所述的式(I)或由式(I)衍生的式的化合物在病媒防治中的用途。
又一方面涉及种子,其中将如本文所述的式(I)或由式(I)衍生的式的化合物作为包衣成分或作为除包衣之外的另一层或另几层施用于所述种子。
因此,另一个方面涉及一种施用包含至少一种如本文所述的式(I)或由式(I)衍生的式的化合物的包衣的方法,或一种施用如本文所述的式(I)或由式(I)衍生的式的化合物的方法,将所述化合物作为除包衣之外的一层或另几层施用于种子,所述方法包括以下步骤:a)将种子与由如本文所述的式(I)或由式(I)衍生的式的化合物组成的包衣材料或包括如本文所述的式(I)或由式(I)衍生的式的化合物的包衣材料混合,b)富集所得到的经包衣的种子组合物,c)干燥所得到的经富集的种子组合物,d)使所得到的经干燥的种子组合物分散或解附聚。
根据取代基的性质,本文所述的式(I)或由式(I)衍生的式的化合物可任选地呈几何异构体和/或旋光异构体或不同组成的相应异构体混合物的形式。本发明涉及纯的异构体和异构体混合物。
本发明的化合物还可以作为金属络合物存在。
定义
本领域的技术人员应知晓,如果没有明确说明,在本申请中使用的表述“一个”或“一种”根据情况可以意指“一个/种”、“一或多个/种”或“至少一个/种”。
在本申请中,具有可变数量的可能碳原子(C原子)的结构可以称为C碳原子数下限-C碳原子数上限结构(CLL-CUL结构),以便由此进行更具体的规定。实例:烷基可以由3至10个碳原子组成,并且在这种情况下对应于C3-C10-烷基。由碳原子和杂原子构成的环结构可以称为“LL元至UL元”结构。6元环结构的一个实例为甲苯(一个被甲基取代的6元环结构)。
对于本领域技术人员显而易见的是,本申请中给出的实例不应被认为是限制性的,而仅仅是更详细地描述一些实施方案。
在复合取代基中(如羟基烷基或烷氧基或烷基羰基),第二个提及的取代基在每种情况下被连接至基础结构(如羟基甲基:-CH2-OH或甲氧基:-O-CH3或甲基羰基:-C(=O)-CH3)。
在上述式中给出的符号的定义中,使用总体上代表以下取代基的集合性术语:
卤素是指第七主族的元素,优选氟、氯、溴和碘,更优选氟、氯和溴。
根据本发明,“烷基”——其本身或作为化学基团的一部分——代表优选具有1至6个碳原子的直链烃或支链烃,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丙基、1,3-二甲基丁基、1,4-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基和2-乙基丁基。还优选具有1至4个碳原子的烷基,例如尤其是甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基。本发明的烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烯基”——其本身或作为化学基团的一部分——代表优选具有2至6个碳原子和至少一个双键的直链烃或支链烃,例如乙烯基、2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-2-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基。还优选具有2至4个碳原子的烯基,例如尤其是2-丙烯基、2-丁烯基或1-甲基-2-丙烯基。本发明的烯基可以被一个或多个相同或不同的基团取代。
根据本发明,“炔基”——其本身或作为化学基团的一部分——代表优选具有2至6个碳原子和至少一个叁键的直链烃或支链烃,例如2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基和2,5-己二炔基。还优选具有2至4个碳原子的炔基,例如尤其是乙炔基、2-丙炔基或2-丁炔基-2-丙烯基。本发明的炔基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基”——其单独或作为化学基团的一部分——代表优选具有3至10个碳的单环烃、双环烃或三环烃,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、双环[2.2.1]庚基、双环[2.2.2]辛基或金刚烷基。还优选具有3、4、5、6或7个碳原子的环烷基,例如尤其是环丙基或环丁基。本发明的环烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基环烷基”代表优选具有4至10个或4至7个碳原子的单环、双环或三环的烷基环烷基,例如甲基环丙基、乙基环丙基、异丙基环丁基、3-甲基环戊基和4-甲基环己基。还优选具有4、5或7个碳原子的烷基环烷基,例如尤其是乙基环丙基或4-甲基环己基。本发明的烷基环烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基烷基”代表优选具有4至10个或4至7个碳原子的单环、双环或三环的环烷基烷基,例如环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基和环戊基乙基。还优选具有4、5或7个碳原子的环烷基烷基,例如尤其是环丙基甲基或环丁基甲基。本发明的环烷基烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“羟基烷基”代表优选具有1至6个碳原子的直链醇或支链醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇和叔丁醇。还优选具有1至4个碳原子的羟基烷基。本发明的羟基烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷氧基”代表优选具有1至6个碳原子的直链或支链的O-烷基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基。还优选具有1至4个碳原子的烷氧基。本发明的烷氧基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基硫烷基”代表优选具有1至6个碳原子的直链或支链的S-烷基,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基和叔丁硫基。还优选具有1至4个碳原子的烷基硫烷基。本发明的烷基硫烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基亚磺酰基”代表优选具有1至6个碳原子的直链或支链的烷基亚磺酰基,例如甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基和叔丁基亚磺酰基。还优选具有1至4个碳原子的烷基亚磺酰基。本发明的烷基亚磺酰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基磺酰基”代表优选具有1至6个碳原子的直链或支链的烷基磺酰基,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基和叔丁基磺酰基。还优选具有1至4个碳原子的烷基磺酰基。本发明的烷基磺酰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基羰基”代表优选具有2至7个碳原子的直链或支链的烷基-C(=O),例如甲基羰基、乙基羰基、正丙基羰基、异丙基羰基、仲丁基羰基和叔丁基羰基。还优选具有1至4个碳原子的烷基羰基。本发明的烷基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基羰基”代表优选在环烷基部分具有3至10个碳原子的直链或支链的环烷基羰基,例如环丙基羰基、环丁基羰基、环戊基羰基、环己基羰基、环庚基羰基、环辛基羰基、双环[2.2.1]庚基、双环[2.2.2]辛基羰基和金刚烷基羰基。还优选在环烷基部分具有3、5或7个碳原子的环烷基羰基。本发明的环烷基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷氧基羰基”——其单独或作为化学基团的组成——代表优选在烷氧基部分具有1至6个碳原子或具有1至4个碳原子的直链或支链的烷氧基羰基,例如甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、仲丁氧基羰基和叔丁氧基羰基。本发明的烷氧基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基氨基羰基”代表优选在烷基部分具有1至6个碳原子或1至4个碳原子的直链或支链的烷基氨基羰基,例如甲基氨基羰基、乙基氨基羰基、正丙基氨基羰基、异丙基氨基羰基、仲丁基氨基羰基和叔丁基氨基羰基。本发明的烷基氨基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“N,N-二烷基氨基羰基”代表优选在烷基部分具有1至6个碳原子或1至4个碳原子的直链或支链的N,N-二烷基氨基羰基,例如N,N-二甲基氨基羰基、N,N-二乙基氨基羰基、N,N-二(正丙基氨基)羰基、N,N-二(异丙基氨基)羰基和N,N-二(仲丁基氨基)羰基。本发明的N,N-二烷基氨基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“芳基”代表优选具有6至14个、特别是6至10个环碳原子的单环、双环或多环芳族体系,例如苯基、萘基、蒽基、菲基,优选苯基。另外,芳基还代表多环体系,例如四氢萘基、茚基、茚满基、芴基、联苯基,其中键合位点在芳族体系上。本发明的芳基可以被一个或多个相同或不同的基团取代。
取代的芳基的实例为芳基烷基,其同样可在C1-C4-烷基和/或C6-C14-芳基部分中被一个或多个相同或不同的基团取代。这样的芳基烷基的实例包括苄基和1-苯基乙基。
根据本发明,“杂环”、“杂环族环”或“杂环体系”代表具有至少一个环的碳环体系,其中至少一个碳原子被杂原子替代,优选被选自N、O、S、P、B、Si、Se的杂原子替代,并且其为饱和的、不饱和的或杂芳族的,并且可以是未取代的或取代的,其中键合位点位于环原子上。除非另有定义,所述杂环优选含有3至9个环原子,尤其是3至6个环原子,并且杂环中含有1个或多个、优选1至4个、尤其是1、2或3个优选选自N、O和S的杂原子,但是两个氧原子不能直接相邻。杂环通常含有不超过4个氮原子和/或不超过2个氧原子和/或不超过2个硫原子。如果杂环基团或杂环任选被取代,则其可以与其他碳环或杂环稠合。在任选取代的杂环基的情况下,本发明还包括多环体系,例如8-氮杂双环[3.2.1]辛基或1-氮杂双环[2.2.1]庚基。在任选取代的杂环基的情况下,本发明还包括螺环体系,例如1-氧杂-5-氮杂螺[2.3]己基。
本发明的杂环基为,例如哌啶基、哌嗪基、吗啉基、硫代吗啉基、二氢吡喃基、四氢吡喃基、二氧杂环己烷基(dioxanyl)、吡咯啉基、吡咯烷基、咪唑啉基、咪唑烷基、噻唑烷基、噁唑烷基、二氧戊环基、间二氧杂环戊烯基、吡唑烷基、四氢呋喃基、二氢呋喃基、氧杂环丁烷基(oxetanyl)、氧杂环丙烷基(oxiranyl)、氮杂环丁烷基(azetidinyl)、氮杂环丙烷基(aziridinyl)、氧氮杂环丁烷基(oxazetidinyl)、氧氮杂环丙烷基(oxaziridinyl)、氧氮杂环庚烷基(oxazepanyl)、氧氮杂环己烷基(oxazinanyl)、氮杂环庚烷基(azepanyl)、氧代吡咯烷基、二氧代吡咯烷基、氧代吗啉基、氧代哌嗪基和氧杂环庚烷基(oxepanyl)。
亚杂芳基(即杂芳族体系)具有特别的含义。根据本发明,表述“杂芳基”代表杂芳族化合物,即被上述杂环定义所涵盖的完全不饱和的芳族杂环化合物,优选具有1至3个、优选1或2个相同或不同的选自上述基团的杂原子的5元至7元环。本发明的杂芳基为,例如,呋喃基、噻吩基、吡唑基、咪唑基、1,2,3-三唑基和1,2,4-三唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,3,4-噁二唑基、1,2,4-噁二唑基和1,2,5-噁二唑基、氮杂基(azepinyl)、吡咯基、吡啶基、哒嗪基、嘧啶基、吡嗪基、1,3,5-三嗪基、1,2,4-三嗪基和1,2,3-三嗪基、1,2,4-噁嗪基、1,3,2-噁嗪基、1,3,6-噁嗪基和1,2,6-噁嗪基、氧杂环庚三烯基(oxepinyl)、硫杂环庚三烯基(thiepinyl)、1,2,4-三唑酮基和1,2,4-二氮杂基。本发明的杂芳基也可以被一个或多个相同或不同的基团取代。
表述“(任选)取代的”基团/取代基,例如取代的烷基、烯基、炔基、烷氧基、烷基硫烷基、烷基亚磺酰基、烷基磺酰基、环烷基、芳基、苯基、苄基、杂环基和杂芳基,意指例如由未取代的基础结构获得的取代的基团,其中取代基为例如一个(1)取代基或多于一个取代基,优选1、2、3、4、5、6或7个取代基,其选自:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰基、C1-C4-羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基和C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,通过双键连接的取代基,例如C1-C4-亚烷基(例如亚甲基或亚乙基)、氧代基、亚氨基以及取代的亚氨基。特别优选的取代的基团为卤代的基团。它们可具有一个或多个卤素取代基,但这些基团也具有至少一个C-H键,或它们可被全卤代。
以举例方式提及的取代基(“第一取代基级别”)如果包含含烃部分,则其可以任选地在该含烃部分被进一步取代(“第二取代基级别”),例如被一个或多个各自独立地选自以下的取代基取代:卤素、羟基、氨基、硝基、氰基、异氰基、叠氮基、酰氨基、氧代基和亚氨基。术语“(任选)取代的”基团优选正好包括一个或两个取代基级别。
本发明的卤素取代的化学基团或卤代基团(例如烷基或烷氧基)被卤素单取代或多取代,直至最大可能的取代基数目。这类基团也称为卤代基团(例如卤代烷基)。在被卤素多取代的情况下,卤素原子可相同或不同,并且可以全部键合到一个碳原子或可以键合到多个碳原子上。在本文中,卤素特别代表氟、氯、溴或碘,优选氟、氯或溴,且更优选氟或Cl。更具体而言,卤素取代的基团为单卤代环烷基,例如1-氟环丙基、2-氟环丙基或1-氟环丁基;单卤代烷基,例如2-氯乙基、2-氟乙基、1-氯乙基、1-氟乙基、氯甲基或氟甲基;全卤代烷基,例如三氯甲基或三氟甲基或CF2CF3;多卤代烷基,例如二氟甲基、2-氟-2-氯乙基、二氯甲基、1,1,2,2-四氟乙基或2,2,2-三氟乙基。卤代烷基的其他实例为三氯甲基、氯二氟甲基、二氯氟甲基、氯甲基、溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2,2,2-三氯乙基、2-氯-2,2-二氟乙基、五氟乙基、3,3,3-三氟丙基和五氟叔丁基。优选这样的卤代烷基:其具有1至4个碳原子和1至9个、优选1至5个相同或不同的选自氟、氯和溴的卤素原子。特别优选具有1或2个碳原子和1至5个相同或不同的选自氟和氯的卤素原子的卤代烷基,例如尤其是二氟甲基、三氟甲基或2,2-二氟乙基。被卤素取代的化合物的其他实例为:卤代烷氧基,例如OCF3、OCHF2、OCH2F、OCF2CF3、OCH2CF3、OCH2CHF2和OCH2CH2Cl;卤代烷基硫烷基,例如二氟甲硫基、三氟甲硫基、三氯甲硫基、氯二氟甲硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、1,1,2,2-四氟乙硫基、2,2,2-三氟乙硫基或2-氯-1,1,2-三氟乙硫基;卤代烷基亚磺酰基,例如二氟甲基亚磺酰基、三氟甲基亚磺酰基、三氯甲基亚磺酰基、氯二氟甲基亚磺酰基、1-氟乙基亚磺酰基、2-氟乙基亚磺酰基、2,2-二氟乙基亚磺酰基、1,1,2,2-四氟乙基亚磺酰基、2,2,2-三氟乙基亚磺酰基和2-氯-1,1,2-三氟乙基亚磺酰基;卤代烷基亚磺酰基,例如二氟甲基亚磺酰基、三氟甲基亚磺酰基、三氯甲基亚磺酰基、氯二氟甲基亚磺酰基、1-氟乙基亚磺酰基、2-氟乙基亚磺酰基、2,2-二氟乙基亚磺酰基、1,1,2,2-四氟乙基亚磺酰基、2,2,2-三氟乙基亚磺酰基和2-氯-1,1,2-三氟乙基亚磺酰基;卤代烷基磺酰基,例如二氟甲基磺酰基、三氟甲基磺酰基、三氯甲基磺酰基、氯二氟甲基磺酰基、1-氟乙基磺酰基、2-氟乙基磺酰基、2,2-二氟乙基磺酰基、1,1,2,2-四氟乙基磺酰基、2,2,2-三氟乙基磺酰基和2-氯-1,1,2-三氟乙基磺酰基。
对于具有碳原子的基团,优选具有1至4个碳原子、尤其是1或2个碳原子的那些基团。通常优选选自以下的取代基:卤素,例如氟和氯;(C1-C4)烷基,优选甲基或乙基;(C1-C4)卤代烷基,优选三氟甲基;(C1-C4)烷氧基,优选甲氧基或乙氧基;(C1-C4)卤代烷氧基;硝基和氰基。本文特别优选以下取代基:甲基、甲氧基、氟和氯。
取代的氨基如单取代或二取代的氨基为选自下述的取代的氨基的基团,即所述氨基例如被一个或两个相同或不同的选自以下的基团N-取代:烷基、羟基、氨基、烷氧基、酰基和芳基;优选为N-单烷基氨基和N,N-二烷基氨基(例如,甲基氨基、乙基氨基、N,N-二甲基氨基、N,N-二乙基氨基、N,N-二正丙基氨基、N,N-二异丙基氨基或N,N-二丁基氨基)、N-单烷氧基烷基氨基或N,N-二烷氧基烷基氨基(例如,N-甲氧基甲基氨基、N-甲氧基乙基氨基、N,N-二(甲氧基甲基)氨基或N,N-二(甲氧基乙基)氨基)、N-单芳基氨基和N,N-二芳基氨基(如任选取代的苯胺)、酰基氨基、N,N-二酰基氨基、N-烷基-N-芳基氨基、N-烷基-N-酰基氨基以及饱和的N-杂环;优选具有1至4个碳原子的烷基;芳基优选为苯基或取代的苯基;酰基如下进一步所定义,优选(C1-C4)烷酰基。这同样适用于取代的羟氨基或肼基。
根据本发明,术语“环状氨基”包括具有一个或多个氮原子的杂芳族环或脂族环体系。杂环是饱和或不饱和的,由一个或多个任选稠合的环体系组成,并且任选地包含其他杂原子,例如一个或两个氮、氧和/或硫原子。此外,该术语还包括具有螺环或桥环体系的基团。形成环状氨基的原子数没有限制,并且例如在单环体系的情况下可为3至8个环原子,在双环体系的情况下可为7至11个原子。
具有氮原子作为杂原子的饱和和不饱和的单环基团的环状氨基的实例包括:1-氮杂环丁烷基、吡咯烷基、2-吡咯烷-1-基、1-吡咯基、哌啶基、1,4-二氢吡嗪-1-基、1,2,5,6-四氢吡嗪-1-基、1,4-二氢吡啶-1-基、1,2,5,6-四氢吡啶-1-基、高哌啶基;具有两个或更多个氮原子作为杂原子的饱和和不饱和的单环基团的环状氨基的实例包括:1-咪唑烷基、1-咪唑基、1-吡唑基、1-三唑基、1-四唑基、1-哌嗪基、1-高哌嗪基、1,2-二氢哌嗪-1-基、1,2-二氢嘧啶-1-基、全氢化嘧啶-1-基、1,4-二氮杂环庚烷-1-基;具有一个或两个氧原子和一个至三个氮原子作为杂原子的饱和和不饱和的单环基团的环状氨基的实例为:例如,噁唑烷-3-基、2,3-二氢异噁唑-2-基、异噁唑-2-基、1,2,3-噁二嗪-2-基、吗啉基;具有一个至三个氮原子和一个至二个硫原子作为杂原子的饱和和不饱和的单环基团的环状氨基的实例包括:噻唑烷-3-基、异噻唑啉-2-基、硫代吗啉基或二氧代硫代吗啉基;具有饱和和不饱和的稠合环状基团的环状氨基的实例包括:吲哚-1-基、1,2-二氢苯并咪唑-1-基、全氢吡咯并[1.2-a]吡嗪-2-基;具有螺环基团的环状氨基的实例包括2-氮杂螺[4.5]癸-2-基;具有桥接杂环基团的环状氨基的实例包括2-氮杂双环[2.2.1]庚-7-基。
取代的氨基还包括在氮原子上具有四个有机取代基的季铵化合物(盐)。
任选取代的苯基优选为未取代的或者被相同或不同的基团单取代或多取代、优选最多三取代的苯基,所述基团选自:卤素、(C1-C4)-烷基、(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷氧基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-卤代烷氧基、(C1-C4)-烷基硫烷基、(C1-C4)-卤代烷基硫烷基、氰基、异氰基和硝基,例如邻-甲苯基、间-甲苯基和对-甲苯基、二甲基苯基、2-氯苯基、3-氯苯基和4-氯苯基、2-氟苯基、3-氟苯基和4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基和4-三氟甲基苯基和2-三氯甲基苯基、3-三氯甲基苯基和4-三氯甲基苯基、2,4-二氯苯基、3,5-二氯苯基、2,5-二氯苯基和2,3-二氯苯基、邻-甲氧基苯基、间-甲氧基苯基和对-甲氧基苯基、4-七氟苯基。
任选取代的环烷基优选为未取代的或者被相同或不同的基团单取代或多取代、优选最多三取代的环烷基,所述基团选自:卤素、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷基和C1-C4-卤代烷氧基,尤其是被一个或两个C1-C4-烷基取代的环烷基。
任选取代的杂环基优选为未取代的或者被相同或不同的基团单取代或多取代、优选最多三取代的杂环基,所述基团选自:卤素、氰基、C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-卤代烷基、C1-C4-卤代烷氧基、硝基和氧代,尤其是被选自以下的基团单取代或多取代的杂环基:卤素、C1-C4-烷基、C1-C4-烷氧基、C1-C4-卤代烷基和氧代,最优选被一个或两个C1-C4-烷基取代的杂环基。
烷基取代的杂芳基的实例为呋喃基甲基、噻吩基甲基、吡唑基甲基、咪唑基甲基、1,2,3-三唑基甲基和1,2,4-三唑基甲基、异噁唑基甲基、噻唑基甲基、异噻唑基甲基、1,2,3-噁二唑基甲基、1,3,4-噁二唑基甲基、1,2,4-噁二唑基甲基和1,2,5-噁二唑基甲基、氮杂基甲基、吡咯基甲基、吡啶基甲基、哒嗪基甲基、嘧啶基甲基、吡嗪基甲基、1,3,5-三嗪基甲基、1,2,4-三嗪基甲基和1,2,3-三嗪基甲基、1,2,4-噁嗪基甲基、1,3,2-噁嗪基甲基、1,3,6-噁嗪基甲基和1,2,6-噁嗪基甲基、氧杂环庚三烯基甲基(oxepinylmethyl)、硫杂环庚三烯基甲基(thiepinylmethyl)和1,2,4-二氮杂基甲基。
本发明的化合物可以优选的实施方案存在。本文中所述的各个实施方案可以彼此结合。不包括违反自然规律的结合以及本领域技术人员根据他/她的专业知识由此排除的结合。例如,排除具有三个或更多个相邻氧原子的环结构。
异构体
根据取代基的性质,式(I)的化合物可呈几何异构体和/或旋光异构体或不同组成的相应异构体混合物的形式。这些立体异构体为,例如,对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明包括纯的立体异构体和这些异构体的任何所需的混合物。
方法和用途
本发明还涉及防治动物害虫的方法,其中使式(I)的化合物作用于动物害虫和/或其生境。动物害虫的防治优选在农业和林业中、以及在材料保护中进行。这优选排除手术性或治疗性治疗人体或动物体的方法和在人体或动物体上进行的诊断方法。
本发明还涉及式(I)的化合物作为农药、尤其是作物保护剂的用途。
在本申请的上下文中,术语“农药”总是还包括术语“作物保护剂”。
鉴于式(I)的化合物具有良好的植物耐受性、有利的恒温动物毒性和良好的环境相容性,其适用于下述用途:保护植物和植物器官抵抗生物和非生物胁迫因素,提高采收产量,提高采收物的品质,以及防治在农业、园艺、畜牧业、水产养殖、林业、花园和休闲设施、储存产品和材料的保护以及卫生领域中遇到的动物害虫,尤其是昆虫、蛛形纲动物、蠕虫、线虫和软体动物。
在本专利申请的上下文中,术语“卫生”应理解为意指旨在预防病症——特别是感染性疾病——以及用于保持人类、动物和/或环境健康和/或维持清洁的所有措施、方法和步骤的全部。根据本发明,这特别包括对例如纺织品或主要由玻璃、木材、混凝土、瓷、陶瓷、塑料或金属制成的硬质表面进行清洁、消毒和杀菌,并且使它们保持清洁而没有卫生害虫和/或其粪便的措施。在这方面,本发明再次排除手术性或治疗性治疗人体或动物体的方法和在人体或动物体上进行的诊断方法。
因此,术语“卫生领域”包括其中所述卫生措施、方法和步骤十分重要的所有区域、技术领域和商业应用,例如厨房、面包房、机场、浴室、游泳池、购物中心、酒店、医院、厩舍等的卫生。
因此,术语“卫生害虫”应理解为意指一种或多种这样的动物害虫,其在卫生领域中的存在是成问题的,特别是出于健康的原因。因此,主要目的是尽可能减少或预防卫生领域中的卫生害虫或与其接触。这可以特别通过使用农药来实现,其中该试剂可以预防性使用,也可以仅在侵袭的情况下使用,以防治害虫。还可以使用通过避免或减少与害虫接触而起作用的试剂。卫生害虫为例如下面提及的生物。
因此,术语“卫生保护”包括用于维持和/或改进所述卫生措施、方法和步骤的所有行为。
式(I)的化合物可优选用作农药。它们对通常敏感且具有抗性的物种以及对所有或特定的发育阶段均具有活性。上述害虫包括:
来自节肢动物门(Arthropoda)、尤其是蛛形纲(Arachnida)的害虫,例如,粉螨属种(Acarus spp.),例如粗脚粉螨(Acarus siro);枸杞瘤瘿螨(Aceria kuko)、桔芽瘿螨(Aceria sheldoni);刺皮节蜱属种(Aculops spp.);刺锈螨属种(Aculus spp.),例如Aculus fockeui、苹果刺锈螨(Aculus schlechtendali);钝眼蜱属种(Amblyomma spp.);山楂叶螨(Amphitetranychus viennensis);锐缘蜱属种(Argas spp.);牛蜱属种(Boophilus spp.);短须螨属种(Brevipalpus spp.),例如紫红短须螨(Brevipalpusphoenicis);Bryobia graminum、苜蓿苔螨(Bryobia praetiosa);刺尾蝎属种(Centruroides spp.);皮螨属种(Chorioptes spp.);鸡皮刺螨(Dermanyssus gallinae);屋尘螨(Dermatophagoides pteronyssinus)、粉尘螨(Dermatophagoides farinae);革蜱属种(Dermacentor spp.);始叶螨属种(Eotetranychus spp.),例如核桃始叶螨(Eotetranychus hicoriae);梨上瘿螨(Epitrimerus pyri);真叶螨属种(Eutetranychusspp.),例如班氏真叶螨(Eutetranychus banksi);瘿螨属种(Eriophyes spp.),例如梨叶瘿螨(Eriophyes pyri);家食甜螨(Glycyphagus domesticus);红足土螨(Halotydeusdestructor);半跗线螨属种(Hemitarsonemus spp.),例如茶半跗线螨(Hemitarsonemuslatus)(=Polyphagotarsonemus latus);璃眼蜱属种(Hyalomma spp.);硬蜱属种(Ixodesspp.);寇蛛属种(Latrodectus spp.);斜蛛属种(Loxosceles spp.);秋收恙螨(Neutrombicula autumnalis);Nuphersa属种;小爪螨属种(Oligonychus spp.),例如咖啡小爪螨(Oligonychus coffeae)、Oligonychus coniferarum、冬青小爪螨(Oligonychusilicis)、Oligonychus indicus、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychus pratensis)、石榴小爪螨(Oligonychus punicae)、樟小爪螨(Oligonychusyothersi);纯缘蜱属种(Ornithodorus spp.);禽剌螨属种(Ornithonyssus spp.);全爪螨属种(Panonychus spp.),例如桔全爪螨(Panonychus citri)(=Metatetranychuscitri)、苹果全爪螨(Panonychus ulmi)(=Metatetranychus ulmi);柑芸锈螨(Phyllocoptruta oleivora);Platytetranychus multidigituli;侧多食跗线螨(Polyphagotarsonemus latus);痒螨属种(Psoroptes spp.);扇头蜱属种(Rhipicephalusspp.);根嗜螨属种(Rhizoglyphus spp.);疥螨属种(Sarcoptes spp.);中东金蝎(Scorpiomaurus);狭跗线螨属种(Steneotarsonemus spp.),稻细螨(Steneotarsonemus spinki);跗线螨属种(Tarsonemus spp.),例如乱跗线螨(Tarsonemus confusus)、白跗线螨(Tarsonemus pallidus);叶螨属种(Tetranychus spp.),例如四点红蜘蛛(Tetranychuscanadensis)、红叶螨(Tetranychus cinnabarinus)、土耳其斯坦叶螨(Tetranychusturkestani)、风团叶螨(Tetranychus urticae);阿氏真恙螨(Trombiculaalfreddugesi);Vaejovis属种;番茄刺皮瘿螨(Vasates lycopersici);
来自唇足纲(Chilopoda)的害虫,例如,地蜈蚣属种(Geophilus spp.)、蚰蜒属种(Scutigera spp.);
来自弹尾目或弹尾纲(Collembola)的害虫,例如,武装棘跳虫(Onychiurus armatus)、绿圆跳虫(Sminthurus viridis);
来自倍足纲(Diplopoda)的害虫,例如,千足虫(Blaniulus guttulatus);
来自昆虫纲(Insecta)的害虫,例如蜚蠊目(Blattodea),例如,东方蜚蠊(Blattaorientalis)、亚洲蜚蠊(Blattella asahinai)、德国蜚蠊(Blattella germanica);马德拉蜚蠊(Leucophaea maderae);Loboptera decipiens;家屋斑蠊(Neostylopygarhombifolia);古巴蠊属种(Panchlora spp.);木蠊属种(Parcoblatta spp.);大蠊属种(Periplaneta spp.),例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplanetaaustralasiae);蔗蠊(Pycnoscelus surinamensis);棕带蜚蠊(Supella longipalpa);
来自鞘翅目(Coleoptera)的害虫,例如,条纹南瓜甲虫(Acalymma vittatum);菜豆象(Acanthoscelides obtectus);喙丽金龟属种(Adoretus spp.);Aethina tumida;杨树萤叶甲(Agelastica alni);叩甲属种(Agriotes spp.),例如直条叩头虫(Agrioteslinneatus)、小麦金针虫(Agriotes mancus);小粉虫(Alphitobius diaperinus);马铃薯鳃角金龟(Amphimallon solstitialis);家具窃蠹(Anobium punctatum);星天牛属种(Anoplophora spp.);花象属种(Anthonomus spp.),例如墨西哥棉铃象虫(Anthonomusgrandis);圆皮蠹属种(Anthrenus spp.);长喙小象属种(Apion spp.);甘蔗金龟属种(Apogonia spp.);隐食甲属种(Atomaria spp.),例如甜菜隐食甲(Atomaria linearis);毛皮蠹属种(Attagenus spp.);Baris caerulescens;恶条豆象(Bruchidius obtectus);豆象属种(Bruchus spp.),例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus);龟甲属种(Cassida spp.);菜豆莹叶甲(Cerotoma trifurcata);象甲属种(Ceutorrhynchus spp.),例如白菜籽龟象(Ceutorrhynchus assimilis)、Ceutorrhynchusquadridens、Ceutorrhynchus rapae;凹胫跳甲属种(Chaetocnema spp.),例如甘薯叶甲(Chaetocnema confinis)、Chaetocnema denticulata、Chaetocnema ectypa;方喙象属种(Cleonus mendicus);宽胸叩头虫属种(Conoderus spp.);根颈象属种(Cosmopolitesspp.),例如香蕉根茎象(Cosmopolites sordidus);褐新西兰肋翅鳃角金龟(Costelytrazealandica);叩甲属种(Ctenicera spp.);象虫属种(Curculio spp.),例如核桃象甲(Curculio caryae)、Curculio caryatrypes、榛子象甲(Curculio obtusus)、Curculiosayi;锈赤扁谷盗(Cryptolestes ferrugineus)、长角扁谷盗(Cryptolestes pusillus);杨干隐喙象(Cryptorhynchus lapathi)、Cryptorhynchus mangiferae;细枝象属种(Cylindrocopturus spp.),密点细枝象(Cylindrocopturus adspersus)、Cylindrocopturus furnissi;皮蠹属种(Dermestes spp.);叶甲属种(Diabrotica spp.),例如黄瓜条叶甲(Diabrotica balteata)、北方玉米根虫(Diabrotica barberi)、十一星叶甲食根亚虫(Diabrotica undecimpunctata howardi)、十一星黄瓜甲虫(Diabroticaundecimpunctata undecimpunctata)、西部玉米根虫(Diabrotica virgiferavirgifera)、玉米根虫(Diabrotica virgifera zeae);蛀野螟属种(Dichocrocis spp.);水稻铁甲(Dicladispa armigera);Diloboderus属种;芽象甲属种(Epicaerus spp.);食植瓢虫属种(Epilachna spp.),例如南瓜瓢虫(Epilachna borealis)、墨西哥豆象(Epilachna varivestis);毛跳甲属种(Epitrix spp.),例如黄瓜跳甲(Epitrixcucumeris)、Epitrix fuscula、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrix tuberis);Faustinus属种;裸蛛甲(Gibbiumpsylloides);阔角谷盗(Gnathocerus cornutus);菜心螟(Hellula undalis);黑异爪蔗金龟(Heteronychus arator);寡节鳃金龟属种(Heteronyx spp.);Hylamorpha elegans;北美家天牛(Hylotrupes bajulus);紫苜蓿叶象(Hypera postica);蓝绿象(Hypomecessquamosus);咪小蠹属种(Hypothenemus spp.),例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemus obscurus)、Hypothenemus pubescens;甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea);烟草甲(Lasioderma serricorne);长头谷盗(Latheticusoryzae);Lathridius属种;合爪负泥虫属种(Lema spp.);马铃薯甲虫(Leptinotarsadecemlineata);银潜蛾属种(Leucoptera spp.),例如咖啡潜叶蛾(Leucopteracoffeella);稻根象(Lissorhoptrus oryzophilus);Listronotus(=Hyperodes)属种;筒喙象属种(Lixus spp.);Luperodes属种;黄胸叶甲(Luperomorpha xanthodera);粉蠹属种(Lyctus spp.);美洲叶甲属种(Megascelis spp.);梳爪叩头虫属种(Melanotus spp.),例如Melanotus longulus oregonensis;油菜花露尾甲(Meligethes aeneus);鳃金龟属种(Melolontha spp.),例如大栗鳃角金龟(Melolontha melolontha);Migdolus属种;墨天牛属种(Monochamus spp.);象甲(Naupactus xanthographus);隐跗郭公虫属种(Necrobiaspp.);Neogalerucella属种;黄蛛甲(Niptus hololeucus);椰蛀犀金龟(Oryctesrhinoceros);锯谷盗(Oryzaephilus surinamensis);Oryzaphagus oryzae;黑葡萄耳象属种(Otiorhynchus spp.),例如Otiorhynchus cribricollis、Otiorhynchus ligustici、草莓耳喙象(Otiorhynchus ovatus)、草莓根耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳象(Otiorhynchus sulcatus);负泥虫属种(Oulema spp.),例如黑角负泥虫(Oulemamelanopus)、稻负泥虫(Oulema oryzae);小青花金龟(Oxycetonia jucunda);辣根猿叶虫(Phaedon cochleariae);鳃角金龟属种(Phyllophaga spp),Phyllophaga helleri;条跳甲属种(Phyllotreta spp.),例如辣根菜跳甲(Phyllotreta armoraciae)、柔弱黑跳甲(Phyllotreta pusilla)、Phyllotreta ramosa、黄曲条菜跳甲(Phyllotreta striolata);日本丽金龟(Popillia japonica);象甲属种(Premnotrypes spp.);大谷蠹(Prostephanustruncatus);蚤跳甲属种(Psylliodes spp.),例如Psylliodes affinis、油菜金头跳甲(Psylliodes chrysocephala)、Psylliodes punctulata;蛛甲属种(Ptinus spp.);暗色瓢虫(Rhizobius ventralis);面炮蠹(Rhizopertha dominica);隐喙象属种(Rhynchophorusspp.),红棕象甲(Rhynchophorus ferrugineus)、棕榈象甲(Rhynchophorus palmarum);Sinoxylon perforans;米象属种(Sitophilus spp.),例如麦子象鼻虫(Sitophilusgranarius)、Sitophilus linearis、米象(Sitophilus oryzae)、玉米象(Sitophiluszeamais);尖隐喙象属种(Sphenophorus spp.);药材甲(Stegobium paniceum);茎干象属种(Sternechus spp.),例如豆茎象(Sternechus paludatus);Symphyletes属种;纤毛象属种(Tanymecus spp.),例如Tanymecus dilaticollis、Tanymecus indicus、Tanymecuspalliatus;黄粉虫(Tenebrio molitor);大谷盗(Tenebrioides mauretanicus);拟谷盗属种(Tribolium spp.),例如Tribolium audax、赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Tribolium confusum);斑皮蠹属种(Trogoderma spp.);籽象属种(Tychius spp.);脊虎天牛属种(Xylotrechus spp.);距步甲属种(Zabrus spp.),例如玉米距步甲(Zabrustenebrioides);
来自革翅目(Dermaptera)的害虫,例如Anisolabis maritime、欧洲球螋(Forficulaauricularia)、红蠼螋(Labidura riparia);
来自双翅目(Diptera)的害虫,例如,伊蚊属种(Aedes spp.),例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、刺扰伊蚊(Aedesvexans);潜蝇属种(Agromyza spp.),例如苜蓿斑潜蝇(Agromyza frontella)、Agromyzaparvicornis;按实蝇属种(Anastrepha spp.);按蚊属种(Anopheles spp.),例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae);瘿蚊属种(Asphondylia spp.);果实蝇属种(Bactrocera spp.),例如瓜实蝇(Bactroceracucurbitae)、东方果实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae);花园毛蚊(Bibio hortulanus);红头丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina);地中海实蝇(Ceratitis capitata);摇蚊属种(Chironomus spp.);金蝇属种(Chrysomya spp.);斑虻属种(Chrysops spp.);高额麻虻(Chrysozonapluvialis);锥蝇属种(Cochliomya spp.);康瘿蚊属种(Contarinia spp.),例如Contarinia johnsoni、甘蓝瘿蚊(Contarinia nasturtii)、梨叶瘿蚊(Contariniapyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱瘿蚊(Contarinia sorghicola)、麦黄吸浆虫(Contarinia tritici);嗜人瘤蝇(Cordylobia anthropophaga);Cricotopussylvestris;库蚊属种(Culex spp.),例如尖音库蚊(Culex pipiens)、致倦库蚊(Culexquinquefasciatus);库蠓属种(Culicoides spp.);脉毛蚊属种(Culiseta spp.);黄蝇属种(Cuterebra spp.);橄榄实蝇(Dacus oleae);叶瘿蚊属种(Dasineura spp.),例如油菜荚叶瘿蚊(Dasineura brassicae);地种蝇属种(Delia spp.),例如葱地种蝇(Deliaantiqua)、麦地种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Deliaplatura)、甘蓝地种蝇(Delia radicum);人皮蝇(Dermatobia hominis);果蝇属种(Drosophila spp.),例如黄猩猩果蝇(Drosphila melanogaster)、樱桃果蝇(Drosophilasuzukii);稻象属种(Echinocnemus spp.);Euleia heraclei;厕蝇属种(Fannia spp.);胃蝇属种(Gasterophilus spp.);舌蝇属种(Glossina spp.);麻虻属种(Haematopotaspp.);毛眼水蝇属种(Hydrellia spp.);大麦水蝇(Hydrellia griseola);种蝇属种(Hylemya spp.);虱蝇属种(Hippobosca spp.);皮下蝇属种(Hypoderma spp.);斑潜蝇属种(Liriomyza spp.),例如菜斑潜蝇(Liriomyza brassicae)、南美斑潜蝇(Liriomyzahuidobrensis)、美洲斑潜蝇(Liriomyza sativae);绿蝇属种(Lucilia spp.),例如铜绿蝇(Lucilia cuprina);罗蛉属种(Lutzomyia spp.);曼蚊属种(Mansonia spp.);家蝇属种(Musca spp.),例如家蝇(Musca domestica)、舍蝇(Musca domestica vicina);狂蝇属种(Oestrus spp.);瑞典麦秆蝇(Oscinella frit);Paratanytarsus属种;Paralauterborniella subcincta;泉蝇属种(Pegomya或Pegomyia spp.),例如甜菜蝇(Pegomya betae)、甜菜潜叶蝇(Pegomya hyoscyami)、悬钩子泉蝇(Pegomya rubivora);白蛉属种(Phlebotomus spp.);草种蝇属种(Phorbia spp.);伏蝇属种(Phormia spp.);酪蝇(Piophila casei);Platyparea poeciloptera;Prodiplosis属种;胡萝卜茎蝇(Psilarosae);绕实蝇属种(Rhagoletis spp.),例如樱桃实蝇(Rhagoletis cingulata)、核桃绕实蝇(Rhagoletis completa)、黑樱桃实蝇(Rhagoletis fausta)、西部樱桃实蝇(Rhagoletis indifferens)、蓝橘绕实蝇(Rhagoletis mendax)、苹果实蝇(Rhagoletispomonella);麻蝇属种(Sarcophaga spp.);蚋属种(Simulium spp.),例如南方蚋(Simulium meridionale);螫蝇属种(Stomoxys spp.);虻属种(Tabanus spp.);根斑蝇属种(Tetanops spp.);大蚊属种(Tipula spp.),例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex);番木瓜长尾实蝇(Toxotrypana curvicauda);
来自半翅目(Hemiptera)的害虫,例如,Acizzia acaciaebaileyanae、Acizziadodonaeae、Acizzia uncatoides;长头蝗(Acrida turrita);无网长管蚜属种(Acyrthosipon spp.),例如碗豆长管蚜(Acyrthosiphon pisum);Acrogonia属种;沫蝉属种(Aeneolamia spp.);隆脉木虱属种(Agonoscena spp.);刺粉虱属种(Aleurocanthusspp.);欧洲甘蓝粉虱(Aleyrodes proletella);甘蔗穴粉虱(Aleurolobus barodensis);软毛粉虱(Aleurothrixus floccosus);Allocaridara malayensis;芒果叶蝉属种(Amrasca spp.),例如Amrasca bigutulla、叶蝉(Amrasca devastans);飞廉短尾蚜(Anuraphis cardui);肾圆盾介壳虫属种(Aonidiella spp.),例如橘红肾圆盾介壳虫(Aonidiella aurantii)、黄圆蹄盾蚧(Aonidiella citrina)、赤圆介壳虫(Aonidiellainornata);苏联黄粉蚜(Aphanostigma piri);蚜属种(Aphis spp.),例如苹果黄蚜(Aphiscitricola)、豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、Aphis forbesi、大豆蚜(Aphis glycines)、棉蚜(Aphis gossypii)、Aphis hederae、Aphis illinoisensis、Aphismiddletoni、鼠李马铃薯蚜(Aphis nasturtii)、夹竹桃蚜(Aphis nerii)、苹果蚜(Aphispomi)、绣线菊蚜(Aphis spiraecola)、Aphis viburniphila;葡萄叶蜂(Arboridiaapicalis);Arytainilla属种;小圆盾蚧属种(Aspidiella spp.);薄圆盾介壳虫属种(Aspidiotus spp.),例如常春藤圆盾蚧(Aspidiotus nerii);Atanus属种;茄沟无网蚜(Aulacorthum solani);烟粉虱(Bemisia tabaci);Blastopsylla occidentalis;Boreioglycaspis melaleucae;李短尾蚜(Brachycaudus helichrysi);微管蚜属种(Brachycolus spp.);甘蓝蚜(Brevicoryne brassicae);喀木虱属种(Cacopsylla spp.),例如梨木虱(Cacopsylla pyricola);小褐稻虱(Calligypona marginata);Capulinia属种;黄头大叶蝉(Carneocephala fulgida);甘蔗绵蚜(Ceratovacuna lanigera);沫蝉科(Cercopidae);蜡蚧属种(Ceroplastes spp.);草莓钉蚜(Chaetosiphon fragaefolii);蔗黄雪盾蚧(Chionaspis tegalensis);茶绿叶蜂(Chlorita onukii);台湾大蝗(Chondracris rosea);核桃黑斑蚜(Chromaphis juglandicola);褐圆蚧(Chrysomphalusaonidum)、黑褐圆盾蚧(Chrysomphalus ficus);玉米叶蝉(Cicadulina mbila);Coccomytilus halli;软蚧属种(Coccus spp.),例如褐软蚧(Coccus hesperidum)、长椭圆软蚧(Coccus longulus)、橘软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿软蚧(Coccusviridis);隐瘤蚜(Cryptomyzus ribis);Cryptoneossa属种;Ctenarytaina属种;角顶叶蝉属种(Dalbulus spp.);Dialeurodes chittendeni、柑橘粉虱(Dialeurodes citri);柑橘木虱(Diaphorina citri);白背盾蚧属种(Diaspis spp.);Diuraphis属种;Doralis属种;草履介壳虫属种(Drosicha spp.);西圆尾蚜属种(Dysaphis spp.),例如Dysaphisapiifolia、车前圆尾蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphis tulipae);灰粉蚧属种(Dysmicoccus spp.);小绿叶蝉属种(Empoasca spp.),例如Empoasca abrupta、马铃薯小绿叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、Empoascasolana、Empoasca stevensi;绵蚜属种(Eriosoma spp.),例如Eriosoma americanum、苹果绵蚜(Eriosoma lanigerum)、Eriosoma pyricola;斑叶蝉属种(Erythroneura spp.);Eucalyptolyma属种;褐木虱属种(Euphyllura spp.);Euscelis bilobatus;弗氏粉蚧属种(Ferrisia spp.);Fiorinia属种;Furcaspis oceanica;咖啡地粉蚧(Geococcuscoffeae);Glycaspis属种;银合欢木虱(Heteropsylla cubana)、Heteropsyllaspinulosa;假桃病毒叶蝉(Homalodisca coagulata);桃大尾蚜(Hyalopterusarundinis)、桃粉蚜(Hyalopterus pruni);吹绵蚧属种(Icerya spp.),例如吹绵蚧(Icerya purchasi);片角叶蝉属种(Idiocerus spp.);扁喙叶蝉属种(Idioscopus spp.);灰飞虱(Laodelphax striatellus);蜡蚧属种(Lecanium spp.),例如褐盔蜡蚧(Lecaniumcorni)(=Parthenolecanium corni);牡蛎蚧属种(Lepidosaphes spp.),例如榆蛎盾蚧(Lepidosaphes ulmi);萝卜蚜(Lipaphis erysimi);日本长片盾介壳虫(Lopholeucaspisjaponica);斑衣蜡蝉(Lycorma delicatula);长管蚜属种(Macrosiphum spp.),例如马铃薯长管蚜(Macrosiphum euphorbiae)、Macrosiphum lilii、蔷薇长管蚜(Macrosiphumrosae);二点叶蜂(Macrosteles facifrons);突眼长蝽属种(Mahanarva spp.);高粱蚜(Melanaphis sacchari);Metcalfiella属种;Metcalfa pruinosa;麦无网蚜(Metopolophium dirhodum);黑缘平翅斑蚜(Monellia costalis);Monelliopsispecanis;瘤蚜属种(Myzus spp.),例如冬葱蚜(Myzus ascalonicus)、Myzus cerasi、Myzusligustri、Myzus ornatus、桃蚜(Myzus persicae)、烟蚜(Myzus nicotianae);莴苣衲长管蚜(Nasonovia ribisnigri);Neomaskellia属种;黑尾叶蝉属种(Nephotettix spp.),例如黑尾叶蝉(Nephotettix cincticeps)、二条斑黑尾叶蝉(Nephotettix nigropictus);Nettigoniclla spectra;稻褐飞虱(Nilaparvata lugens);Oncometopia属种;Ortheziapraelonga;中华稻蝗(Oxya chinensis);Pachypsylla属种;杨梅缘粉虱(Parabemisiamyricae);木虱属种(Paratrioza spp.),例如Paratrioza cockerelli;片盾蚧属种(Parlatoria spp.);瘿绵蚜属种(Pemphigus spp.),例如囊柄瘿绵蚜(Pemphigusbursarius)、Pemphigus populivenae;玉米蜡蝉(Peregrinus maidis);扁角飞虱属种(Perkinsiella spp.);绵粉蚧属种(Phenacoccus spp.),例如苏铁褐点并盾蚧(Phenacoccus madeirensis);杨平翅绵蚜(Phloeomyzus passerinii);忽布疣蚜(Phorodon humuli);葡萄根瘤蚜属种(Phylloxera spp.),例如Phylloxera devastatrix、Phylloxera notabilis;苏铁褐点并盾蚧(Pinnaspis aspidistrae);臀纹粉蚧属种(Planococcus spp.),例如枯臀纹粉蚧(Planococcus citri);Prosopidopsylla flava;梨形原绵蚧(Protopulvinaria pyriformis);桑白盾蚧(Pseudaulacaspis pentagona);粉蚧属种(Pseudococcus spp.),例如嗜桔粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、长尾粉蚧(Pseudococcus longispinus)、真葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni);Psyllopsis属种;木虱属种(Psylla spp.),例如Psylla buxi、苹果木虱(Psylla mali)、梨木虱(Psylla pyri);金小蜂属种(Pteromalus spp.);Pulvinaria属种;Pyrilla属种;笠圆盾蚧属种(Quadraspidiotus spp.),例如胡桃圆盾蚧(Quadraspidiotus juglansregiae)、Quadraspidiotus ostreaeformis、梨圆盾蚧(Quadraspidiotus perniciosus);Quesadagigas;平刺粉蚧属种(Rastrococcus spp.);缢管蚜属种(Rhopalosiphum spp.),例如玉米蚜(Rhopalosiphum maidis)、Rhopalosiphum oxyacanthae、禾谷缢管蚜(Rhopalosiphumpadi)、红腹缢管蚜(Rhopalosiphum rufiabdominale);黑盔蚧属种(Saissetia spp.),例如咖啡硬介壳虫(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、橄榄黑盔蚧(Saissetia oleae);葡萄带叶蝉(Scaphoideus titanus);麦二叉蚜(Schizaphisgraminum);苏铁刺圆盾蚧(Selenaspidus articulatus);Sipha flava;麦长管蚜(Sitobion avenae);长唇基飞虱属种(Sogata spp.);白背飞虱(Sogatella furcifera);Sogatodes属种;三角蝶(Stictocephala festina);树粉虱(Siphoninus phillyreae);Tenalaphara malayensis;Tetragonocephela属种;美洲山核桃长斑蚜(Tinocalliscaryaefoliae);广胸沫蝉属种(Tomaspis spp.);声蚜属种(Toxoptera spp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus);温室白粉虱(Trialeurodesvaporariorum);尖翅木虱属种(Trioza spp.),例如Trioza diospyri;小叶蝉属种(Typhlocyba spp.);尖盾蚧属种(Unaspis spp.);葡萄根瘤虱(Viteus vitifolii);么叶蝉属种(Zygina spp.);
来自异翅亚目(Heteroptera)的害虫,例如,麦蝽属种(Aelia spp.);南瓜缘蝽(Anasatristis);拟丽蝽属种(Antestiopsis spp.);Boisea属种;土长蝽属种(Blissus spp.);俊盲蝽属种(Calocoris spp.);斑腿微刺盲蝽(Campylomma livida);异背长蝽属种(Cavelerius spp.);臭虫属种(Cimex spp.),例如Cimex adjunctus、热带臭虫(Cimexhemipterus)、温带臭虫(Cimex lectularius)、蝠臭虫(Cimex pilosellus);白瓣麦寄蝇属种(Collaria spp.);绿盲蝽(Creontiades dilutus);胡椒缘蝽(Dasynus piperis);Dichelops furcatus;厚氏长棒网蝽(Diconocoris hewetti);棉红蝽属种(Dysdercusspp.);美洲蝽属种(Euschistus spp.),例如Euschistus heros、褐臭蝽(Euschistusservus)、Euschistus tristigmus、Euschistus variolarius;菜蝽属种(Eurydema spp.);扁盾蝽属种(Eurygaster spp.);茶翅蝽(Halyomorpha halys);刺盲蝽属种(Heliopeltisspp.);Horcias nobilellus;稻缘蝽属种(Leptocorisa spp.);异稻缘蝽(Leptocorisavaricornis);Leptoglossus occidentalis;叶足缘蝽(Leptoglossus phyllopus);丽盲蝽属种(Lygocoris spp.),例如原丽盲蝽(Lygocoris pabulinus);草盲蝽属种(Lygusspp.),例如Lygus elisus、豆荚盲蝽(Lygus hesperus)、牧草盲蝽(Lygus lineolaris);蔗黑长蝽(Macropes excavatus);筛豆龟蝽(Megacopta cribraria);盲蝽科(Miridae);黑摩盲蝽(Monalonion atratum);绿蝽属种(Nezara spp.),例如稻绿蝽(Nezara viridula);小长蝽属种(Nysius spp.);稻蝽属种(Oebalus spp.);Pentomidae;方背皮蝽(Piesmaquadrata);壁蝽属种(Piezodorus spp.),例如Piezodorus guildinii;杂盲蝽属种(Psallus spp.);Pseudacysta persea;长红猎蝽属种(Rhodnius spp.);可可褐盲蝽(Sahlbergella singularis);Scaptocoris castanea;黑蝽属种(Scotinophora spp.);梨冠网蝽(Stephanitis nashi);Tibraca属种;锥猎蝽属种(Triatoma spp.);
来自膜翅目(Hymenoptera)的害虫,例如,顶切叶蚁属种(Acromyrmex spp.);菜叶蜂属种(Athalia spp.),例如黄翅菜叶蜂(Athalia rosae);切叶蚁属种(Atta spp.);弓背蚁属种(Camponotus spp.);长黄胡蜂属(Dolichovespula spp.);松叶蜂属种(Diprion spp.),例如类欧松叶蜂(Diprion similis);实叶蜂属种(Hoplocampa spp.),例如樱实叶蜂(Hoplocampa cookei)、苹叶蜂(Hoplocampa testudinea);毛蚁属种(Lasius spp.);阿根廷蚁(Linepithema(Iridiomyrmex)humile);小家蚁(Monomorium pharaonis);立毛蚁属种(Paratrechina spp.);Paravespula属种;斜结蚁属种(Plagiolepis spp.);树蜂属种(Sirex spp.);红火蚁(Solenopsis invicta);蚁属种(Tapinoma spp.);白足狡臭蚁(Technomyrmex albipes);树蜂属种(Urocerus spp.);胡蜂属种(Vespa spp.),例如黄边胡蜂(Vespa crabro);小火蚁(Wasmannia auropunctata);黑树蜂属种(Xeris spp.);
来自等足目(Isopoda)的害虫,例如,鼠妇(Armadillidium vulgare)、栉水虱(Oniscusasellus)、球鼠妇(Porcellio scaber);
来自等翅目(Isoptera)的害虫,例如,家白蚁属种(Coptotermes spp.),例如台湾乳白蚁(Coptotermes formosanus);堆角白蚁(Cornitermes cumulans);堆砂白蚁属种(Cryptotermes spp.);楹白蚁属种(Incisitermes spp.);木白蚁属种(Kalotermesspp.);稻麦小白蚁(Microtermes obesi);象白蚁属种(Nasutitermes spp.);土白蚁属种(Odontotermes spp.);洞白蚁属种(Porotermes spp.);散白蚁属种(Reticulitermesspp.),例如黄肢散白蚁(Reticulitermes flavipes)、西方散白蚁(Reticulitermeshesperus);
来自鳞翅目(Lepidoptera)的害虫,例如,小蜡螟(Achroia grisella);桑剑纹夜蛾(Acronicta major);褐带卷蛾属种(Adoxophyes spp.),例如棉褐带卷蛾(Adoxophyesorana);烦夜蛾(Aedia leucomelas);地老虎属种(Agrotis spp.),例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon);波纹夜蛾属种(Alabama spp.),例如棉叶波纹夜蛾(Alabama argillacea);脐橙螟蛾(Amyelois transitella);条麦蛾属种(Anarsiaspp.);干煞夜蛾属种(Anticarsia spp.),例如大豆夜蛾(Anticarsia gemmatalis);条小卷蛾属种(Argyroploce spp.);Autographa属种;甘蓝夜蛾(Barathra brassicae);Blastodacna atra;籼弄蝶(Borbo cinnara);棉潜蛾(Bucculatrix thurberiella);松尺蠖(Bupalus piniarius);蛀褐夜蛾属种(Busseola spp.);卷叶蛾属种(Cacoecia spp.);茶细蛾(Caloptilia theivora);烟卷蛾(Capua reticulana);苹果蠹蛾(Carpocapsapomonella);桃柱果蛾(Carposina niponensis);冬尺蛾(Cheimatobia brumata);禾草螟属种(Chilo spp.),例如禾草螟(Chilo plejadellus)、二化螟(Chilo suppressalis);苹果舞蛾(Choreutis pariana);色卷蛾属种(Choristoneura spp.);Chrysodeixischalcites;葡萄果蠹蛾(Clysia ambiguella);纵卷叶野螟属种(Cnaphalocerus spp.);稻纵卷叶螟(Cnaphalocrocis medinalis);云卷蛾属种(Cnephasia spp.);细蛾属种(Conopomorpha spp.);球颈象属种(Conotrachelus spp.);Copitarsia属种;小卷蛾属种(Cydia spp.),例如豌豆小卷蛾(Cydia nigricana)、苹果小卷蛾(Cydia pomonella);Dalaca noctuides;绢野螟属种(Diaphania spp.);Diparopsis属种;小蔗螟(Diatraeasaccharalis);钻夜蛾属种(Earias spp.);Ecdytolopha aurantium;南美玉米苗斑螟(Elasmopalpus lignosellus);非洲蔗螟(Eldana saccharina);粉斑螟属种(Ephestiaspp.),例如烟草粉螟(Ephestia elutella)、地中海粉螟(Ephestia kuehniella);叶小卷蛾属种(Epinotia spp.);苹淡褐卷蛾(Epiphyas postvittana);Erannis属种;Erschoviella musculana;荚斑螟属种(Etiella spp.);Eudocima属种;棕卷蛾属种(Euliaspp.);女贞细卷蛾(Eupoecilia ambiguella);黄毒蛾属种(Euproctis spp.),例如褐尾蠹(Euproctis chrysorrhoea);切夜蛾属种(Euxoa spp.);脏切夜蛾属种(Feltia spp.);大蜡螟(Galleria mellonella);细蛾属种(Gracillaria spp.);小食心虫属种(Grapholithaspp.),例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholita prunivora);蚀叶野螟属种(Hedylepta spp.);铃夜蛾属种(Helicoverpa spp.),例如棉铃虫(Helicoverpa armigera)、玉米穗虫(Helicoverpa zea);实夜蛾属种(Heliothis spp.),例如烟芽夜蛾(Heliothis virescens);褐织蛾(Hofmannophila pseudospretella);同斑螟属种(Homoeosoma spp.);长卷蛾属种(Homona spp.);苹果巢蛾(Hyponomeutapadella);柿蒂虫(Kakivoria flavofasciata);亮灰蝶属种(Lampides spp.);贪夜蛾属种(Laphygma spp.);梨小食心虫(Laspeyresia molesta);茄黄斑螟蛾(Leucinodesorbonalis);潜叶蛾属种(Leucoptera spp.),例如咖啡潜叶蛾(Leucoptera coffeella);潜叶细蛾属种(Lithocolletis spp.),例如Lithocolletis blancardella;绿果冬夜蛾(Lithophane antennata);花翅小卷蛾属种(Lobesia spp.),例如葡萄花翅小卷蛾(Lobesia botrana);白缘豆夜蛾(Loxagrotis albicosta);毒蛾属种(Lymantria spp.),例如舞毒蛾(Lymantria dispar);潜蛾属种(Lyonetia spp.),例如桃潜蛾(Lyonetiaclerkella);黄褐天幕毛虫(Malacosoma neustria);豆荚野螟(Maruca testulalis);甘蓝夜蛾(Mamestra brassicae);暮眼蝶(Melanitis leda);毛胫夜蛾属种(Mocis spp.);Monopis obviella;东方粘虫(Mythimna separata);Nemapogon cloacellus;水螟属种(Nymphula spp.);Oiketicus属种;Omphisa属种;秋尺蛾属种(Operophtera spp.);麦秆夜蛾属种(Oria spp.);瘤丛螟属种(Orthaga spp.);秆野螟属种(Ostrinia spp.),例如欧洲玉米螟(Ostrinia nubilalis);小眼夜蛾(Panolis flammea);稻弄蝶属种(Parnaraspp.);红铃麦蛾属种(Pectinophora spp.),例如棉红铃虫(Pectinophora gossypiella);潜跳甲属种(Perileucoptera spp.);块茎蛾属种(Phthorimaea spp.),例如马铃薯块茎蛾(Phthorimaea operculella);桔潜蛾(Phyllocnistis citrella);小潜细蛾属种(Phyllonorycter spp.),例如斑幕潜叶蛾(Phyllonorycter blancardella)、Phyllonorycter crataegella;菜粉蝶属种(Pieris spp.),例如菜青虫(Pieris rapae);荷兰石竹小卷蛾(Platynota stultana);印度谷蛾(Plodia interpunctella);金翅夜蛾属种(Plusia spp.);小菜蛾(Plutella xylostella)(=Plutella maculipennis);小白巢蛾属种(Prays spp.);斜纹夜蛾属种(Prodenia spp.);烟草天蛾属种(Protoparce spp.);粘虫属种(Pseudaletia spp.),例如一星粘虫(Pseudaletia unipuncta);大豆尺夜蛾(Pseudoplusia includens);玉米螟(Pyrausta nubilalis);薄荷灰夜蛾(Rachiplusianu);禾螟属种(Schoenobius spp.),例如Schoenobius bipunctifer;白禾螟属种(Scirpophaga spp.),例如稻白螟(Scirpophaga innotata);黄地老虎(Scotia segetum);蛀茎夜蛾属种(Sesamia spp.),例如大螟(Sesamia inferens);长须卷蛾属种(Sparganothis spp.);灰翅夜蛾属种(Spodoptera spp.),例如Spodoptera eradiana、甜菜夜蛾(Spodoptera exigua)、草地贪夜蛾(Spodoptera frugiperda)、Spodopterapraefica;举肢蛾属种(Stathmopoda spp.);Stenoma属种;花生麦蛾(Stomopteryxsubsecivella);兴透翅蛾属种(Synanthedon spp.);安第斯马铃薯块茎蛾(Teciasolanivora);带蛾属种(Thaumetopoea spp.);大显夜蛾(Thermesia gemmatalis);木塞谷蛾(Tinea cloacella)、袋谷蛾(Tinea pellionella);幕谷蛾(Tineola bisselliella);栎绿卷蛾属种(Tortrix spp.);毛毡衣蛾(Trichophaga tapetzella);粉夜蛾属种(Trichoplusia spp.),例如粉纹夜蛾(Trichoplusia ni);三化螟(Tryporyzaincertulas);番茄斑潜蝇(Tuta absoluta);灰蝶属种(Virachola spp.);
来自直翅目(Orthoptera)或跳跃目(Saltatoria)的害虫,例如,家蟋(Achetadomesticus);Dichroplus属种;蝼蛄属种(Gryllotalpa spp.),例如欧洲蝼蛄(Gryllotalpa gryllotalpa);蔗蝗属种(Hieroglyphus spp.);飞蝗属种(Locusta spp.),例如东亚飞蝗(Locusta migratoria);黑蝗属种(Melanoplus spp.),例如Melanoplusdevastator;Paratlanticus ussuriensis;沙漠蝗(Schistocerca gregaria);
来自虱目(Phthiraptera)的害虫,例如,畜虱属种(Damalinia spp.)、血虱属种(Haematopinus spp.)、毛虱属种(Linognathus spp.)、虱属种(Pediculus spp.)、根瘤蚜(Phylloera vastatrix)、阴虱(Phthirus pubis)、嚼虱属种(Trichodectes spp.);
来自啮虫目(Psocoptera)的害虫,例如,粉啮虫属种(Lepinotus spp.)、书虱属种(Liposcelis spp.);
来自蚤目(Siphonaptera)的害虫,例如,角叶蚤属种(Ceratophyllus spp.);栉首蚤属种(Ctenocephalides spp.),例如犬栉首蚤(Ctenocephalides canis)、猫栉头蚤(Ctenocephalides felis);扰蚤(Pulex irritans);穿皮潜蚤(Tunga penetrans);印鼠客蚤(Xenopsylla cheopsis);
来自缨翅目(Thysanoptera)的害虫,例如,玉米黄呆蓟马(Anaphothrips obscurus);稻蓟马(Baliothrips biformis);Chaetanaphothrips leeuweni;鲜食葡萄镰蓟马(Drepanothrips reuteri);Enneothrips flavens;花蓟马属种(Frankliniella spp.),例如烟褐花蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、东方花蓟马(Frankliniella tritici)、Frankliniellavaccinii、威廉期花蓟马(Frankliniella williamsi);Haplothrips属种;阳蓟马属种(Heliothrips spp.);温室条篱蓟马(Hercinothrips femoralis);卡蓟马属种(Kakothrips spp.);葡萄蓟马(Rhipiphorothrips cruentatus);硬蓟马属种(Scirtothrips spp.);Taeniothrips cardamomi;蓟马属种(Thrips spp.),例如南黄蓟马(Thrips palmi)、葱蓟马(Thrips tabaci);
来自衣鱼目(Zygentoma)(=缨尾目(Thysanura))的害虫,例如,栉衣鱼属种(Ctenolepisma spp.)、衣鱼(Lepisma saccharina)、盗火虫(Lepismodes inquilinus)、小灶衣鱼(Thermobia domestica);
来自综合纲(Symphyla)的害虫,例如,么蚰属种(Scutigerella spp.),例如白松虫(Scutigerella immaculata);
来自软体动物门(Mollusca)、特别是双壳纲(Bivalvia)的害虫,例如,贻贝属种(Dreissena spp.),
以及来自腹足纲(Gastropoda)的害虫,例如,阿勇蛞蝓属种(Arion spp.),例如黑蛞蝓(Arionater rufus);双脐螺属种(Biomphalaria spp.);泡螺属种(Bulinus spp.);野蛞蝓属种(Deroceras spp.),例如光滑野蛞蝓(Deroceras laeve);土蜗属种(Galba spp.);椎实螺属种(Lymnaea spp.);钉螺属种(Oncomelania spp.);福寿螺属种(Pomacea spp.);琥珀螺属种(Succinea spp.);
来自扁形动物门(Platyhelminthes)和线虫动物门(Nematoda)的动物寄生虫和人类寄生虫,例如,猫圆线虫属种(Aelurostrongylus spp.)、裂口线虫属种(Amidostomumspp.)、钩口线虫属种(Ancylostoma spp.)(例如十二指肠钩口线虫(Ancylostomaduodenale)、斯里兰卡钩口线虫(Ancylostoma ceylanicum)、巴西钩口线虫(Acylostomabraziliensis))、管圆线虫属种(Angiostrongylus spp.)、异尖线虫属种(Anisakisspp.)、裸头绦虫属种(Anoplocephala spp.)、蛔虫属种(Ascaris spp.)、鸡蛔虫属种(Ascaridia spp.)、贝利蛔虫属种(Baylisascaris spp.)、布鲁线虫属种(Brugia spp.)(例如马来布鲁线虫(Brugia malayi)、帝汶布鲁线虫(Brugia timori))、仰口线虫属种(Bunostomum spp.)、毛细线虫属种(Capillaria spp.)、夏柏特线虫属种(Chabertiaspp.)、支睾吸虫属种(Clonorchis spp.)、古柏线虫属种(Cooperia spp.)、环体线虫属种(Crenosoma spp.)、杯口属种(Cyathostoma spp.)、双腔吸虫属种(Dicrocoelium spp.)、网尾线虫属种(Dictyocaulus spp.)(例如丝状网尾线虫(Dictyocaulus filaria))、裂头绦虫属种(Diphyllobothrium spp.)(例如阔节裂头绦虫(Diphyllobothrium latum))、复孔绦虫属种(Dipylidium spp.)、恶丝虫属种(Dirofilaria spp.)、龙线虫属种(Dracunculus spp.)(例如麦地那龙线虫(Dracunculus medinensis))、棘球绦虫属种(Echinococcus spp.)(例如细粒棘球绦虫(Echinococcus granulosus)、多房棘球绦虫(Echinococcus multilocularis))、棘口吸虫属种(Echinostoma spp.)、蛲虫属种(Enterobius spp.)(例如蠕形住肠蛲虫(Enterobius vermicularis))、真鞘属种(Eucoleus spp.)、片形吸虫属种(Fasciola spp.)、拟片形吸虫属种(Fascioloidesspp.)、姜片虫属种(Fasciolopsis spp.)、类丝虫属种(Filaroides spp.)、筒线属种(Gongylonema spp.)、三代虫属种(Gyrodactylus spp.)、丽线虫属种(Habronema spp.)、血矛线虫属种(Haemonchus spp.)、似绕体线虫属种(Heligmosomoides spp.)、异刺线虫属种(Heterakis spp.)、膜壳绦虫属种(Hymenolepis spp.)(例如Hymenolepis nana)、猪圆形属种(Hyostrongylus spp.)、光丝虫属种(Litomosoides spp.)、罗阿丝虫属种(Loaspp.)(例如罗阿罗阿线虫(LoaLoa))、后圆线虫属种(Metastrongylus spp.)、次睾吸虫属种(Metorchis spp.)、中殖孔绦虫属种(Mesocestoides spp.)、蒙尼茨绦虫属种(Monieziaspp.)、缪勒线虫属种(Muellerius spp.)、板口线虫属种(Necator spp.)、细颈线虫属种(Nematodirus spp.)、日本圆线虫属种(Nippostrongylus spp.)、结节线虫属种(Oesophagostomum spp.)、沃鲁线虫属种(Ollulanus spp.)、盘尾丝虫属种(Onchocercaspp.)(例如旋盘尾丝虫(Onchocerca volvulus))、后睾吸虫属种(Opisthorchis spp.)、奥斯勒线虫属种(Oslerus spp.)、胃线虫属种(Ostertagia spp.)、尖尾线虫属种(Oxyurisspp.)、Paracapillaria属种、副丝虫属种(Parafilaria spp.)、并殖吸虫属种(Paragonimus spp.)、同端盘吸虫属种(Paramphistomum spp.)、副裸头绦虫属种(Paranoplocephala spp.)、副蛔虫属种(Parascaris spp.)、栓尾线虫属种(Passalurusspp.)、原圆线虫属种(Protostrongylus spp.)、血吸虫属种(Schistosoma spp.)、腹腔丝虫属种(Setaria spp.)、旋尾线虫属种(Spirocerca spp.)、冠丝虫属种(Stephanofilariaspp.)、冠尾线属种(Stephanurus spp.)、类圆线虫属种(Strongyloides spp.)(例如富氏类圆线虫(Strongyloides fuelleborni)、粪类圆线虫(Strongyloides stercoralis))、圆线虫属种(Strongylus spp.)、开口虫属种(Syngamus spp.)、带绦虫属种(Taenia spp.)(例如牛带绦虫(Taenia saginata)、猪带绦虫(Taenia solium))、背带线虫属种(Teladorsagia spp.)、吸吮线虫属种(Thelazia spp.)、弓蛔线虫属种(Toxascarisspp.)、弓蛔虫属种(Toxocara spp.)、毛线虫属种(Trichinella spp.)(例如旋毛形线虫(Trichinella spiralis)、本地毛形线虫(Trichinella nativa)、抹布氏旋毛虫(Trichinella britovi)、南方旋毛虫(Trichinella nelsoni)、Trichinellapseudopsiralis)、毛毕吸虫属种(Trichobilharzia spp.)、毛圆线虫属种(Trichostrongylus spp.)、鞭虫属种(Trichuris spp.)(例如Trichuris trichuria)、钩虫属种(Uncinaria spp.)、吴策线虫属种(Wuchereria spp.)(例如班氏吴策线虫(Wuchereria bancrofti));
来自线虫动物门的植物害虫,即植物寄生性线虫,特别是野外垫刃属种(Aglenchus spp.),例如居农野外垫刃线虫(Aglenchus agricola);粒线虫属种(Anguinaspp.),例如小麦粒线虫(Anguina tritici);滑刃线虫属种(Aphelenchoides spp.),例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoidesfragariae);刺线虫属种(Belonolaimus spp.),例如Belonolaimus gracilis、长尾刺线虫(Belonolaimus longicaudatus)、Belonolaimus nortoni;伞滑刃线虫属种(Bursaphelenchus spp.),例如椰子红环腐线虫(Bursaphelenchus cocophilus)、荒漠伞滑刃线虫(Bursaphelenchus eremus)、松材线虫(Bursaphelenchus xylophilus);坏死线虫属种(Cacopaurus spp.),例如Cacopaurus pestis;小环线虫属种(Criconemellaspp.),例如弯曲小环线虫(Criconemella curvata)、俄尼小环线虫(Criconemellaonoensis)、装饰小环线虫(Criconemella ornata)、Criconemella rusium、薄叶小环线虫(Criconemella xenoplax)(=Mesocriconema xenoplax);轮线虫属种(Criconemoidesspp.),例如Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum;茎线虫属种(Ditylenchus spp.),例如鳞球茎茎线虫(Ditylenchus dipsaci);锥线虫属种(Dolichodorus spp.);球异皮线虫属种(Globodera spp.),例如马铃薯白线虫(Globoderapallida)、马铃薯金线虫(Globodera rostochiensis);螺旋线虫属种(Helicotylenchusspp.),例如双宫螺旋线虫(Helicotylenchus dihystera);半轮线虫属种(Hemicriconemoides spp.);鞘线虫属种(Hemicycliophora spp.);异皮线虫属种(Heterodera spp.),例如燕麦异皮线虫(Heterodera avenae)、大豆异皮线虫(Heteroderaglycines)、甜菜异皮线虫(Heterodera schachtii);潜根线虫属种(Hirschmaniellaspp.);纽带线虫属种(Hoplolaimus spp.);长针线虫属种(Longidorus spp.),例如非洲长针线虫(Longidorus africanus);根结线虫属种(Meloidogyne spp.),例如哥伦比亚根结线虫(Meloidogyne chitwoodi)、伪根结线虫(Meloidogyne fallax)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita);Meloinema属种;珍珠线虫属种(Nacobbus spp.);拟茎线虫属种(Neotylenchus spp.);Paralongidorus属种;拟滑刃线虫属种(Paraphelenchus spp.);拟毛刺线虫属种(Paratrichodorus spp.),例如较小拟毛刺线虫(Paratrichodorus minor);针线虫属种(Paratylenchus spp.);短体线虫属种(Pratylenchus spp.),例如穿刺短体线虫(Pratylenchus penetrans);Pseudohalenchus属种;Psilenchus属种;Punctodera属种;五沟线虫属种(Quinisulcius spp.);穿孔线虫属种(Radopholus spp.),例如柑橘穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis);肾型线虫属种(Rotylenchulus spp.);盘旋线虫属种(Rotylenchus spp.);盾线虫属种(Scutellonema spp.);亚蛇形线虫属种(Subanguinaspp.);毛刺线虫属种(Trichodorus spp.),例如Trichodorus obtusus、原始毛刺线虫(Trichodorus primitivus);矮化线虫属种(Tylenchorhynchus spp.),例如饰环矮化线虫(Tylenchorhynchus annulatus);半穿刺线虫属(Tylenchulus spp.),例如柑橘半穿刺线虫(Tylenchulus semipenetrans);剑线虫属种(Xiphinema spp.),例如标准剑线虫(Xiphinema index)。
此外,还可以防治来自原生动物(Protozoa)亚门、球虫目(Coccidia)的害虫,例如艾美球虫属种(Eimeria spp.)。
线虫
在本文中,术语“线虫”包括线虫动物门的所有物种,并且在本文中特别是作为寄生虫作用于植物或真菌的物种(例如,滑刃目(Aphelenchida)、根结线虫属(Meloidogyne)、垫刃目(Tylenchida)等的物种)或作用于人和动物的物种(例如,毛形线虫科(Trichinellida)、垫刃目、杆形目(Rhabditida)和旋尾目(Spirurida)的物种)或在这些活的生物体中或生物体上造成损害的物种,以及其他寄生蠕虫。
如本文所述,作物保护中的杀线虫剂能够防治线虫。
术语“防治线虫”意指杀死线虫或预防或阻止其发育或其生长或者预防或阻止其渗入或吸食植物组织。
在本文中,化合物的功效如下确定:通过比较用式(I)的化合物处理的植物或植物部位或者经处理的土壤与未处理的植物或植物部位或未处理的土壤(100%)之间的线虫死亡率、虫瘿(gall)形成、孢囊(cyst)形成、每体积土壤的线虫密度、每个根部的线虫密度、每体积土壤的线虫卵数量、线虫的活动性。优选地,与未处理的植物、植物部位或未处理的土壤相比,所达到的减少为25-50%,更优选51-79%,且最优选通过达到80%至100%的减少而完全杀灭线虫或完全预防线虫的发育和生长。本文所述的防治线虫还包括防治线虫繁殖(孢囊和/或卵的发育)。式(I)的化合物还可用于保持植物或动物健康,并且它们可治疗性、预防性或内吸性(systemically)地用于防治线虫。
本领域技术人员知晓测定线虫死亡率、虫瘿形成、孢囊形成、每体积土壤的线虫密度、每个根部的线虫密度、每体积土壤的线虫卵数量、线虫的活动性的方法。
使用式(I)的化合物可保持植物健康,并且还包括减少由线虫引起的损害和增加采收产量。
在本文中,术语“线虫”指植物线虫,其包括所有损害植物的线虫。植物线虫包括植物寄生线虫和土传线虫。植物寄生线虫包括体外寄生虫,例如剑线虫属种(Xiphinemaspp.)、长针线虫属种(Longidorus spp.)和毛刺线虫属种(Trichodorus spp.);半寄生虫,例如半穿刺线虫属种(Tylenchulus spp.);迁移性内寄生虫,例如短体线虫属种(Pratylenchus spp.)、穿孔线虫属种(Radopholus spp.)和盾线虫属种(Scutellonemaspp.);非迁移性寄生虫,例如异皮线虫属种(Heterodera spp.)、球异皮线虫属种(Globodera spp.)和根结线虫属种(Meloidogyne spp.);以及茎和叶内寄生虫,例如茎线虫属种(Ditylenchus spp.)、滑刃线虫属种(Aphelenchoides spp.)和潜根线虫属种(Hirshmaniella spp.)。特别有害的根部寄生的土壤线虫为,例如,异皮线虫属或球异皮线虫属的形成孢囊的线虫,和/或根结线虫属的根瘿线虫。这些属的有害物种为,例如,南方根结线虫(Meloidogyne incognita)、大豆异皮线虫(Heterodera glycines)(大豆孢囊线虫)、马铃薯白线虫(Globodera pallida)和马铃薯金线虫(Globodera rostochiensis)(马铃薯孢囊线虫),通过本文所述的化合物可有效防治这些物种。但是,本文所述的化合物的用途绝不限于这些属或物种,而是以相同方式扩展至其他线虫。
植物线虫包括,例如,居农野外垫刃线虫(Aglenchus agricola);小麦粒线虫(Anguina tritici);花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoides fragaria)和滑刃线虫属种(Aphelenchoides spp.)的茎和叶内寄生虫;细小刺线虫(Belonolaimus gracilis)、长尾刺线虫(Belonolaimus longicaudatus)、Belonolaimus nortoni,椰子红环腐线虫(Bursaphelenchus cocophilus)、荒漠伞滑刃线虫(Bursaphelenchus eremus)、松材线虫(Bursaphelenchus xylophilus)和伞滑刃线虫属种(Bursaphelenchus spp.);Cacopaurus pestis;弯曲小环线虫(Criconemellacurvata)、俄尼小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemellaornata)、Criconemella rusium、薄叶小环线虫(Criconemella xenoplax)(=Mesocriconema xenoplax)和小环线虫属种(Criconemella spp.);
Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum和轮线虫属种(Criconemoides spp.);马铃薯茎线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchus dipsaci)、食菌茎线虫(Ditylenchus myceliophagus)以及茎线虫属种(Ditylenchus spp.)的茎和叶内寄生虫;Dolichodorus heterocephalus,马铃薯白线虫(Globodera pallida)(=苍白异皮线虫(Heterodera pallida))、马铃薯金线虫(Globodera rostochiensis)(马铃薯孢囊线虫)、茄球皮线虫(Globodera solanacearum)、烟草孢囊线虫(Globodera tabacum)、弗吉尼亚球皮线虫(Globodera virginia)和球异皮线虫属种(Globodera spp.)的非迁移性的形成孢囊的寄生虫;双角螺旋线虫(Helicotylenchus digonicus)、双宫螺旋线虫(Helicotylenchus dihystera)、刺桐螺旋线虫(Helicotylenchus erythrine)、多带螺旋线虫(Helicotylenchus multicinctus)、短螺旋线虫(Helicotylenchus nannus)、假强壮螺旋线虫(Helicotylenchuspseudorobustus)和螺旋线虫属种(Helicotylenchus spp.);半轮线虫属(Hemicriconemoides);花生鞘线虫(Hemicycliophora arenaria)、Hemicycliophoranudata、微细鞘线虫(Hemicycliophora parvana);燕麦异皮线虫(Heterodera avenae)、十字花科异皮线虫(Heterodera cruciferae)、大豆异皮线虫(Heterodera glycines)(大豆孢囊线虫)、水稻异皮线虫(Heterodera oryzae)、甜菜异皮线虫(Heterodera schachtii)、玉米异皮线虫(Heterodera zeae)和异皮线虫属种(Heterodera spp.)的非迁移性的形成孢囊的寄生虫;纤细潜根线虫(Hirschmaniella gracilis)、水稻潜根线虫(Hirschmaniella oryzae)、刺尾潜根线虫(Hirschmaniella spinicaudata)和潜根线虫属种(Hirschmaniella spp.)的茎和叶内寄生虫,埃及纽带线虫(Hoplolaimus aegyptii)、加利福尼亚纽带线虫(Hoplolaimus californicus)、哥伦比亚纽带线虫(Hoplolaimuscolumbus)、帽状纽带线虫(Hoplolaimus galeatus)、印度纽带线虫(Hoplolaimusindicus)、大针纽带线虫(Hoplolaimus magnistylus)、似强壮纽带线虫(Hoplolaimuspararobustus);非洲长针线虫(Longidorus africanus)、短环长针线虫(Longidorusbreviannulatus)、逃逸长针线虫(Longidorus elongatus)、Longidorus laevicapitatus、Longidorus vineacola和长针线虫属种(Longidorus spp.)的体外寄生虫,高粱根结线虫(Meloidogyne acronea)、非洲根结线虫(Meloidogyne africana)、花生根结线虫(Meloidogyne arenaria)、Meloidogyne arenaria thamesi、甘蓝根结线虫(Meloidogyneartiella)、奇氏根结线虫(Meloidogyne chitwoodi)、咖啡根结线虫(Meloidogynecoffeicola)、埃塞俄比亚根结线虫(Meloidogyne ethiopica)、短小根结线虫(Meloidogyne exigua)、伪根结线虫(Meloidogyne fallax)、禾草根结线虫(Meloidogynegraminicola)、禾本科根结线虫(Meloidogyne graminis)、北方根结线虫(Meloidogynehapla)、南方根结线虫(Meloidogyne incognita)、Meloidogyne incognita acrita、爪哇根结线虫(Meloidogyne javanica)、吉库尤根结线虫(Meloidogyne kikuyensis)、较小根结线虫(Meloidogyne minor)、纳西根结线虫(Meloidogyne naasi)、巴拉纳根结线虫(Meloidogyne paranaensis)、泰晤士根结线虫(Meloidogyne thamesi)和根结线虫属种(Meloidogyne spp.)的非迁移性寄生虫;Meloinema属种;异常珍珠线虫(Nacobbusaberrans);Neotylenchus vigissi;假墙草异滑刃线虫(Paraphelenchuspseudoparietinus);葱拟毛刺线虫(Paratrichodorus allius)、Paratrichodoruslobatus、较小拟毛刺线虫(Paratrichodorus minor)、短小拟毛刺线虫(Paratrichodorusnanus)、胼胝拟毛刺线虫(Paratrichodorus porosus)、光滑拟毛刺线虫(Paratrichodorusteres)和拟毛刺线虫属种(Paratrichodorus spp.),具钩针线虫(Paratylenchushamatus)、微小针线虫(Paratylenchus minutus)、突出针线虫(Paratylenchusprojectus)和针线虫属种(Paratylenchus spp.),敏捷短体线虫(Pratylenchus agilis)、艾伦短体线虫(Pratylenchus alleni)、安第斯短体线虫(Pratylenchus andinus)、最短尾短体线虫(Pratylenchus brachyurus)、谷类短体线虫(Pratylenchus cerealis)、咖啡短体线虫(Pratylenchus coffeae)、刻痕短体线虫(Pratylenchus crenatus)、德拉特短体线虫(Pratylenchus delattrei)、Pratylenchus giibbicaudatus、Pratylenchus goodeyi、具钩短体线虫(Pratylenchus hamatus)、六裂短体线虫(Pratylenchus hexincisus)、卢斯短体线虫(Pratylenchus loosi)、落选短体线虫(Pratylenchus neglectus)、穿刺短体线虫(Pratylenchus penetrans)、草地短体线虫(Pratylenchus pratensis)、斯克里布纳短体线虫(Pratylenchus scribneri)、光滑短体线虫(Pratylenchus teres)、索氏短体线虫(Pratylenchus thornei)、伤残短体线虫(Pratylenchus vulnus)、玉米短体线虫(Pratylenchus zeae)和短体线虫属种(Pratylenchus spp.)的迁移性内寄生虫;Pseudohalenchus minutus;Psilenchus magnidens、尾粗裸矛线虫(Psilenchustumidus);查尔科斑皮线虫(Punctodera chalcoensis),尖锐五沟线虫(Quinisulciusacutus);柑橘穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholussimilis)、穿孔线虫属种(Radopholus spp.)的迁移性内寄生虫,北方肾型线虫(Rotylenchulus borealis)、微小肾型线虫(Rotylenchulus parvus)、肾形肾状线虫(Rotylenchulus reniformis)和肾型线虫属种(Rotylenchulus spp.),直沟盘旋线虫(Rotylenchus laurentinus)、大囊盘旋线虫(Rotylenchus macrodoratus)、强壮盘旋线虫(Rotylenchus robustus)、Rotylenchus uniformis和盘旋线虫属种(Rotylenchus spp.),小尾盾线虫(Scutellonema brachyurum)、缓慢盾线虫(Scutellonema bradys)、Scutellonema clathricaudatum和盾线虫属种(Scutellonema spp.)的迁移性内寄生虫,根瘿亚粒线虫(Subanguina radiciola),烟草细垫线虫(Tetylenchus nicotianae);圆桶毛刺线虫(Trichodorus cylindricus)、小毛刺线虫(Trichodorus minor)、原始毛刺线虫(Trichodorus primitivus)、邻近毛刺线虫(Trichodorus proximus)、相似毛刺线虫(Trichodorus similis)、稀少毛刺线虫(Trichodorus sparsus)和毛刺线虫属种(Trichodorus spp.)的体外寄生虫;农田矮化线虫(Tylenchorhynchus agri)、甘蓝矮化线虫(Tylenchorhynchus brassicae)、清亮矮化线虫(Tylenchorhynchus clarus)、克莱顿矮化线虫(Tylenchorhynchus claytoni)、指状矮化线虫(Tylenchorhynchus digitatus)、Tylenchorhynchus ebriensis、最大矮化线虫(Tylenchorhynchus maximus)、裸矮化线虫(Tylenchorhynchus nudus)、寻常矮化线虫(Tylenchorhynchus vulgaris)和矮化线虫属种(Tylenchorhynchus spp.);柑橘半穿刺线虫(Tylenchulus semipenetrans)和半穿刺线虫属种(Tylenchulus spp.)的半寄生虫;美洲剑线虫(Xiphinema americanum)、短颈剑线虫(Xiphinema brevicolle)、Xiphinema dimorphicaudatum、标准剑线虫(Xiphinemaindex)和剑线虫属种(Xiphinema spp.)的体外寄生虫。
可使用式(I)的化合物来防治的线虫包括:根结线虫属的线虫,例如南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)、北方根结线虫(Meloidogyne hapla)和花生根结线虫(Meloidogyne arenaria);茎线虫属(Ditylenchus)的线虫,例如马铃薯腐烂线虫(马铃薯茎线虫(Ditylenchus destructor))和茎和球茎线虫(鳞球茎茎线虫(Ditylenchus dipsaci));短体线虫属(Pratylenchus)的线虫,例如玉米根损害线虫(穿刺短体线虫(Pratylenchus penetrans))、菊根损害线虫(伪短体线虫(Pratylenchus fallax))、咖啡根损害线虫(咖啡短体线虫(Pratylenchus coffeae))、茶树根损害线虫(卢斯短体线虫(Pratylenchus loosi))和胡桃根损害线虫(伤残短体线虫(Pratylenchus vulnus));球异皮线虫属(Globodera)的线虫,例如黄色马铃薯孢囊线虫(马铃薯金线虫(Globodera rostochiensis))和白色马铃薯孢囊线虫(马铃薯白线虫(Globodera pallida));异皮线虫属(Heterodera)的线虫,例如大豆孢囊线虫(大豆异皮线虫(Heterodera glycines))和甜菜孢囊线虫(甜菜异皮线虫(Heterodera schachtii));滑刃线虫属(Aphelenchoides)的线虫,例如稻干尖线虫(贝西滑刃线虫(Aphelenchoidesbesseyi))、菊叶线虫(菊叶芽滑刃线虫(Aphelenchoides ritzemabosi))和草莓线虫(草莓滑刃线虫(Aphelenchoides fragariae));真滑刃线虫属(Aphelenchus)的线虫,例如食菌线虫(燕麦真滑刃线虫(Aphelenchus avenae));穿孔线虫属(Radopholus)的线虫,例如掘穴线虫(香蕉穿孔线虫(Radopholus similis));半穿刺线虫属(Tylenchulus)的线虫,例如柑橘根线虫(柑橘半穿刺线虫(Tylenchulus semipenetrans));肾型线虫属(Rotylenchulus)的线虫,例如肾形线虫(肾形肾状线虫(Rotylenchulus reniformis));存在于树木中的线虫,例如松木线虫(松材线虫(Bursaphelenchus xylophilus))和红环线虫(椰子红环腐线虫(Bursaphelenchus cocophilus))等。
可使用式(I)的化合物来保护的植物包括以下植物:例如谷物(例如,稻、大麦、小麦、黑麦、燕麦、玉米等)、豆类(大豆、红豆、菜豆、蚕豆、豌豆、花生等)、果树/果实(苹果、柑橘类、梨、葡萄、桃、日本杏、樱桃、胡桃、扁桃、香蕉、草莓等)、蔬菜(甘蓝、番茄、菠菜、花椰菜、莴苣、洋葱、大葱、胡椒等)、根作物(胡萝卜、马铃薯、甘薯、萝卜、莲藕、芜菁等)、工业原料用植物(棉花、大麻、构树、三桠、油菜、甜菜、蛇麻草、甘蔗、糖用甜菜、橄榄、橡胶、棕榈树、咖啡、烟草、茶等)、瓜类(南瓜、黄瓜、西瓜、甜瓜等)、牧草植物(鸭茅草、高粱、梯牧草、三叶草、紫花苜蓿等)、草坪草(结缕草、剪股颖等)、香料植物(薰衣草、迷迭香、百里香、欧芹、胡椒、姜等)等,以及花(菊花、玫瑰、兰花等)。
式(I)的化合物特别适用于防治咖啡线虫,特别是最短尾短体线虫(Pratylenchusbrachyurus)、咖啡短体线虫(Pratylenchus coffeae)、短小根结线虫(Meloidogyneexigua)、南方根结线虫(Meloidogyne incognita)、咖啡根结线虫(Meloidogynecoffeicola)、螺旋线虫属种(Helicotylenchus spp.)以及巴拉纳根结线虫(Meloidogyneparanaensis)、盘旋线虫属种(Rotylenchus spp.)、剑线虫属种(Xiphinema spp.)、矮化线虫属种(Tylenchorhynchus spp.)和盾线虫属种(Scutellonema spp.)。
式(I)的化合物特别适用于防治马铃薯线虫,特别是最短尾短体线虫、草地短体线虫、斯克里布纳短体线虫、穿刺短体线虫、咖啡短体线虫、鳞球茎茎线虫以及艾伦短体线虫、安第斯短体线虫、谷类短体线虫、刻痕短体线虫、六裂短体线虫、卢斯短体线虫、落选短体线虫、光滑短体线虫、索氏短体线虫、伤残短体线虫、长尾刺线虫、圆桶毛刺线虫、原始毛刺线虫、邻近毛刺线虫、相似毛刺线虫、稀少毛刺线虫、较小拟毛刺线虫、葱拟毛刺线虫、短小拟毛刺线虫、光滑拟毛刺线虫、花生根结线虫、伪根结线虫、北方根结线虫、泰晤士根结线虫、南方根结线虫、奇氏根结线虫、爪哇根结线虫、异常珍珠线虫、马铃薯金线虫、马铃薯白线虫、马铃薯茎线虫、相似穿孔线虫、肾形肾状线虫、Neotylenchus vigissi、假墙草异滑刃线虫、草莓滑刃线虫和Meloinema属种。
式(I)的化合物特别适用于防治番茄线虫,特别是花生根结线虫、北方根结线虫、爪哇根结线虫、南方根结线虫、穿刺短体线虫以及最短尾短体线虫、咖啡短体线虫、斯克里布纳短体线虫、伤残短体线虫、较小拟毛刺线虫、短小根结线虫、异常珍珠线虫、茄球皮线虫、Dolichodorus heterocephalus和肾形肾状线虫。
式(I)的化合物特别适用于防治黄瓜植物线虫,特别是花生根结线虫、北方根结线虫、爪哇根结线虫、南方根结线虫、肾形肾状线虫和索氏短体线虫。
式(I)的化合物特别适用于防治棉花线虫,特别是长尾刺线虫、南方根结线虫、哥伦比亚纽带线虫、帽状纽带线虫和肾形肾状线虫。
式(I)的化合物特别适用于防治玉米线虫,特别是长尾刺线虫、较小拟毛刺线虫以及最短尾短体线虫、德拉特短体线虫、六裂短体线虫、穿刺短体线虫、玉米短体线虫、(细小刺线虫)、Belonolaimus nortoni、短环长针线虫、花生根结线虫、Meloidogyne arenariathamesi、禾本科根结线虫、南方根结线虫、Meloidogyne incognita acrita、爪哇根结线虫、纳西根结线虫、燕麦异皮线虫、水稻异皮线虫、玉米异皮线虫、查尔科斑皮线虫、鳞球茎茎线虫、埃及纽带线虫、大针纽带线虫、帽状纽带线虫、印度纽带线虫、双角螺旋线虫、双宫螺旋线虫、假强壮螺旋线虫、美洲剑线虫、Dolichodorus heterocephalus、装饰小环线虫、俄尼小环线虫、相似穿孔线虫、北方肾型线虫、微小肾型线虫、农田矮化线虫、清亮矮化线虫、克莱顿矮化线虫、最大矮化线虫、裸矮化线虫、寻常矮化线虫、尖锐五沟线虫、微小针线虫、微细鞘线虫、居农野外垫刃线虫、小麦粒线虫、花生滑刃线虫、小尾盾线虫和根瘿亚粒线虫。
式(I)的化合物特别适用于防治大豆线虫,特别是最短尾短体线虫、草地短体线虫、穿刺短体线虫、斯克里布纳短体线虫、长尾刺线虫、大豆异皮线虫、哥伦比亚纽带线虫以及咖啡短体线虫、六裂短体线虫、落选短体线虫、刻痕短体线虫、艾伦短体线虫、敏捷短体线虫、玉米短体线虫、伤残短体线虫、(细小刺线虫)、花生根结线虫、南方根结线虫、爪哇根结线虫、北方根结线虫、哥伦比亚纽带线虫、帽状纽带线虫和肾形肾状线虫。
式(I)的化合物特别适用于防治烟草线虫,特别是南方根结线虫、爪哇根结线虫以及最短尾短体线虫、草地短体线虫、六裂短体线虫、穿刺短体线虫、落选短体线虫、刻痕短体线虫、索氏短体线虫、伤残短体线虫、玉米短体线虫、逃逸长针线虫、Paratrichodoruslobatus、毛刺线虫属种、花生根结线虫、北方根结线虫、烟草孢囊线虫、茄球皮线虫、弗吉尼亚球皮线虫、鳞球茎茎线虫、盘旋线虫属种、螺旋线虫属种、美洲剑线虫、小环线虫属种、肾形肾状线虫、克莱顿矮化线虫、针线虫属种和烟草细垫线虫。
式(I)的化合物特别适用于防治柑橘线虫,特别是咖啡短体线虫以及最短尾短体线虫、伤残短体线虫、长尾刺线虫、较小拟毛刺线虫、胼胝拟毛刺线虫、毛刺线虫属、南方根结线虫、Meloidogyne incognita acrita、爪哇根结线虫、大囊盘旋线虫、美洲剑线虫、短颈剑线虫、标准剑线虫、小环线虫属种、半轮线虫属、香蕉穿孔线虫和柑橘穿孔线虫、花生鞘线虫、Hemicycliophora nudata和柑橘半穿刺线虫。
式(I)的化合物特别适用于防治香蕉线虫,特别是咖啡短体线虫、香蕉穿孔线虫以及Pratylenchus giibbicaudatus、卢斯短体线虫、根结线虫属种、多带螺旋线虫、双宫螺旋线虫和肾型线虫属种。
式(I)的化合物特别适用于防治菠萝线虫,特别是玉米短体线虫、草地短体线虫、最短尾短体线虫、Pratylenchus goodeyi、根结线虫属种、肾形肾状线虫以及逃逸长针线虫、Longidorus laevicapitatus、原始毛刺线虫、小毛刺线虫、异皮线虫属种、食菌茎线虫、加利福尼亚纽带线虫、似强壮纽带线虫、印度纽带线虫、双宫螺旋线虫、短螺旋线虫、多带螺旋线虫、刺桐螺旋线虫、Xiphinema dimorphicaudatum、香蕉穿孔线虫、指状矮化线虫、Tylenchorhynchus ebriensis、微小针线虫、Scutellonema clathricaudatum、缓慢盾线虫、尾粗裸矛线虫、Psilenchus magnidens、Pseudohalenchus minutus、Criconemoidesferniae、Criconemoides onoense和Criconemoides ornatum。
式(I)的化合物特别适用于防治葡萄线虫,特别是伤残短体线虫、花生根结线虫、南方根结线虫、爪哇根结线虫、美洲剑线虫、标准剑线虫以及草地短体线虫、斯克里布纳短体线虫、落选短体线虫、最短尾短体线虫、索氏短体线虫和柑橘半穿刺线虫。
式(I)的化合物特别适用于防治树木作物——仁果中的线虫,特别是穿刺短体线虫以及伤残短体线虫、逃逸长针线虫、南方根结线虫和北方根结线虫。
式(I)的化合物特别适用于防治树木作物——核果中的线虫,特别是穿刺短体线虫、伤残短体线虫、花生根结线虫、北方根结线虫、爪哇根结线虫、南方根结线虫、薄叶小环线虫以及最短尾短体线虫、咖啡短体线虫、斯克里布纳短体线虫、玉米短体线虫、长尾刺线虫、双宫螺旋线虫、美洲剑线虫、弯曲小环线虫、克莱顿矮化线虫、具钩针线虫、突出针线虫、小尾盾线虫和帽状纽带线虫。
式(I)的化合物特别适用于防治树木作物、甘蔗和稻中的线虫,特别是毛刺线虫属种、小环线虫属种以及短体线虫属种、拟毛刺线虫属种、根结线虫属种、螺旋线虫属种、矮化线虫属种、滑刃线虫属种、异皮线虫属种、剑线虫属种和Cacopaurus pestis。
在本文中,术语“线虫”还指损害人或动物的线虫。
对人或动物有害的具体的线虫物种为:
毛形线虫科(Trichinellida),例如:鞭虫属种(Trichuris spp.)、毛细线虫属种(Capillaria spp.)、Paracapillaria属种、优鞘属种(Eucoleus spp.)、Trichomosoides属种、毛线虫属种(Trichinella spp.);
垫刃目(Tylenchida),例如:细丝鲶属种(Micronema spp.)、类圆线虫属种(Strongyloides spp.);
杆形目(Rhabditida),例如:圆线虫属种(Strongylus spp.)、三齿属种(Triodontophorus spp.)、食道齿属种(Oesophagodontus spp.)、毛线属种(Trichonemaspp.)、辐首线虫属种(Gyalocephalus spp.)、柱咽属种(Cylindropharynx spp.)、杯口线虫属种(Poteriostomum spp.)、Cyclococercus属种、杯冠属种(Cylicostephanus spp.)、结节线虫属种(Oesophagostomum spp.)、夏柏特线虫属种(Chabertia spp.)、肾线虫属种(Stephanurus spp.)、钩口线虫属种(Ancylostoma spp.)、钩虫属种(Uncinaria spp.)、板口线虫属种(Necator spp.)、仰口线虫属种(Bunostomum spp.)、球头线虫属种(Globocephalus spp.)、比翼线虫属种(Syngamus spp.)、杯口线虫属种(Cyathostomaspp.)、后圆线虫属种(Metastrongylus spp.)、网尾线虫属种(Dictyocaulus spp.)、缪勒线虫属种(Muellerius spp.)、原圆线虫属种(Protostrongylus spp.)、新圆线虫属种(Neostrongylus spp.)、囊尾线虫属种(Cystocaulus spp.)、肺圆线虫属种(Pneumostrongylus spp.)、Spicocaulus属种、麂圆线虫属种(Elaphostrongylus spp.)、拟马鹿圆线虫属种(Parelaphostrongylus spp.)、环体线虫属种(Crenosoma spp.)、Paracrenosoma属种、奥斯勒丝虫属种(Oslerus spp.)、管圆线虫属种(Angiostrongylusspp.)、猫圆线虫属种(Aelurostrongylus spp.)、类丝虫属种(Filaroides spp.)、副类丝虫属种(Parafilaroides spp.)、毛圆线虫属种(Trichostrongylus spp.)、血矛线虫属种(Haemonchus spp.)、胃线虫属种(Ostertagia spp.)、背带线虫属种(Teladorsagiaspp.)、马歇尔线虫属种(Marshallagia spp.)、古柏线虫属种(Cooperia spp.)、日圆线虫属种(Nippostrongylus spp.)、似绕体线虫属种(Heligmosomoides spp.)、细颈线虫属种(Nematodirus spp.)、猪圆线虫属种(Hyostrongylus spp.)、尖柱线虫属种(Obeliscoidesspp.)、裂口线虫属种(Amidostomum spp.)、沃鲁线虫属种(Ollulanus spp.);
旋尾目(Spirurida),例如:尖尾线虫属种(Oxyuris spp.)、蛲虫属种(Enterobiusspp.)、栓尾线虫属种(Passalurus spp.)、管状线虫属种(Syphacia spp.)、无刺线虫属种(Aspiculuris spp.)、异刺线虫属种(Heterakis spp.);蛔虫属种(Ascaris spp.)、弓蛔线虫属种(Toxascaris spp.)、弓蛔虫属种(Toxocara spp.)、贝利蛔线虫属种(Baylisascaris spp.)、副蛔虫属种(Parascaris spp.)、异尖线虫属种(Anisakis spp.)、鸡蛔虫属种(Ascaridia spp.);颚口线虫属种(Gnathostoma spp.)、泡翼线虫属种(Physaloptera spp.)、吸吮线虫属种(Thelazia spp.)、筒线虫属种(Gongylonema spp.)、丽线虫属种(Habronema spp.)、副柔线虫属种(Parabronema spp.)、德拉西线虫属种(Draschia spp.)、龙线虫属种(Dracunculus spp.);冠丝虫属种(Stephanofilariaspp.)、副丝虫属种(Parafilaria spp.)、腹腔丝虫属种(Setaria spp.)、罗阿丝虫属种(Loa spp.)、恶丝虫属种(Dirofilaria spp.)、光丝虫属种(Litomosoides spp.)、布鲁线虫属种(Brugia spp.)、吴策线虫属种(Wuchereria spp.)、盘尾丝虫属种(Onchocercaspp.)、旋尾线虫属种(Spirocerca spp.)。
许多已知的杀线虫剂还作用于其它寄生蠕虫,并因此用于防治作为人体和动物中的寄生虫的蠕虫——不一定属于线虫类。本发明还涉及式(I)的化合物作为抗蠕虫的药剂的用途。病原性内寄生蠕虫包括扁形动物门(Platyhelmintha)(例如,单殖亚纲(Monogenea)、绦虫类(cestodes)和吸虫类(trematodes))、棘头动物门(Acanthocephala)和舌形动物门(Pentastoma)。可优选提及以下蠕虫:
单殖亚纲:例如,三代虫属种(Gyrodactylus spp.)、指环虫属种(Dactylogyrusspp.)、多盘吸虫属种(Polystoma spp.);
绦虫类:假叶目(Pseudophyllidea),例如,裂头属种(Diphyllobothrium spp.)、迭宫绦虫属种(Spirometra spp.)、裂头绦虫属种(Schistocephalus spp.)、舌状绦虫属种(Ligula spp.)、突盘绦虫属种(Bothridium spp.)、复殖孔绦虫属种(Diphlogonoporusspp.);
圆叶目(Cyclophyllida),例如,中殖孔绦虫属种(Mesocestoides spp.)、裸头绦虫属种(Anoplocephala spp.)、副裸头绦虫属种(Paranoplocephala spp.)、蒙尼茨绦虫属种(Moniezia spp.)、繸体绦虫属种(Thysanosoma spp.)、曲子宫绦虫属种(Thysanieziaspp.)、无卵黄腺绦虫属种(Avitellina spp.)、斯泰绦虫属种(Stilesia spp.)、鸣绦虫属种(Cittotaenia spp.)、Andyra属种、伯特绦虫属种(Bertiella spp.)、带绦虫属种(Taenia spp.)、棘球绦虫属种(Echinococcus spp.)、泡尾绦虫属种(Hydatigera spp.)、戴文氏绦虫属种(Davainea spp.)、瑞立绦虫属种(Raillietina spp.)、膜壳绦虫属种(Hymenolepis spp.)、棘鳞绦虫属种(Echinolepis spp.)、Echinocotyle属种、双睾绦虫属种(Diorchis spp.)、复孔绦虫属种(Dipylidium spp.)、约优克斯绦虫属种(Joyeuxiellaspp.)、复孔绦虫属种(Diplopylidium spp.);
吸虫类:复殖纲(Digenea),例如,双穴吸虫属种(Diplostomum spp.)、茎双穴吸虫属种(Posthodiplostomum spp.)、血吸虫属种(Schistosoma spp.)、毛毕吸虫属种(Trichobilharzia spp.)、鸟毕吸虫属种(Ornithobilharzia spp.)、澳毕吸虫属种(Austrobilharzia spp.)、巨毕吸虫属种(Gigantobilharzia spp.)、彩蚴吸虫属种(Leucochloridium spp.)、短咽吸虫属种(Brachylaima spp.)、棘口吸虫属种(Echinostoma spp.)、棘缘吸虫属种(Echinoparyphium spp.)、棘隙吸虫属种(Echinochasmus spp.)、低颈吸虫属种(Hypoderaeum spp.)、片形吸虫属种(Fasciolaspp.)、Fasciolides属种、姜片吸虫属种(Fasciolopsis spp.)、环腔吸虫属种(Cyclocoelum spp.)、盲腔吸虫属种(Typhlocoelum spp.)、同盘吸虫属种(Paramphistomum spp.)、杯殖吸虫属种(Calicophoron spp.)、殖盘吸虫属种(Cotylophoron spp.)、巨孔吸虫属种(Gigantocotyle spp.)、菲策吸虫属种(Fischoederius spp.)、腹袋吸虫属种(Gastrothylacus spp.)、背孔吸虫属种(Notocotylus spp.)、下弯吸虫属种(Catatropis spp.)、斜睾吸虫属种(Plagiorchisspp.)、前殖吸虫属种(Prosthogonimus spp.)、双腔吸虫属种(Dicrocoelium spp.)、阔盘吸虫属种(Eurytrema spp.)、隐孔吸虫属种(Troglotrema spp.)、并殖吸虫属种(Paragonimus spp.)、肛瘤吸虫属种(Collyriclum spp.)、侏形吸虫属种(Nanophyetusspp.)、后睾吸虫属种(Opisthorchis spp.)、支睾吸虫属种(Clonorchis spp.)、次睾吸虫属种(Metorchis spp.)、异形吸虫属种(Heterophyes spp.)、后殖吸虫属种(Metagonimusspp.);
棘头动物门:少棘目(Oligacanthorhynchida),例如,巨吻棘头虫属种(Macracanthorhynchus spp.)、前睾棘头虫属种(Prosthenorchis spp.);多形目(Polymorphida),例如,细颈棘头虫属种(Filicollis spp.);念珠目(Moniliformida),例如,念珠棘虫属种(Moniliformis spp.);
棘吻目(Echinorhynchida),例如,棘头虫属种(Acanthocephalus spp.)、棘吻虫属种(Echinorhynchus spp.)、似细吻棘头虫属种(Leptorhynchoides spp.);
舌形动物门:蛇舌状虫目(Porocephalida),例如舌形虫属种(Linguatula spp.)。
在兽医领域和动物饲养中,式(I)的化合物的给药通过已知的方式直接或经肠内、经胃肠外、经皮或经鼻以合适的使用形式进行。给药可为预防性的或治疗性的。
在某些浓度或施用率下,式(I)的化合物视情况还可用作除草剂、安全剂、生长调节剂或用于改善植物特性的试剂,用作杀微生物剂或杀配子剂,例如用作杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括抵抗类病毒的试剂)或用作抗MLO(类支原体生物)和RLO(类立克次氏体生物)的试剂。它们视情况还可用作用于合成其他活性化合物的中间体或前体。
制剂
本发明还涉及包含至少一种式(I)的化合物的制剂和由其制备的作为农药的使用形式,例如浸液、滴液和喷液。任选地,所述使用形式还包含具有改善作用的其他农药和/或佐剂,如渗透剂,例如植物油(如油菜籽油、葵花籽油)、矿物油(如石蜡油)、植物脂肪酸的烷基酯(如菜籽油甲酯或大豆油甲酯)或烷醇烷氧基化物;和/或展着剂(spreader),例如烷基硅氧烷和/或盐(例如有机或无机铵盐或鏻盐,如硫酸铵或磷酸氢二铵);和/或保持促进剂,例如磺基琥珀酸二辛酯或羟丙基瓜儿胶聚合物;和/或保湿剂,例如甘油;和/或肥料,例如铵肥、钾肥或磷肥。
常规制剂为例如水溶性液剂(SL)、乳油(EC)、水乳剂(EW)、悬浮浓缩剂(SC、SE、FS、OD)、水分散性颗粒剂(WG)、颗粒剂(GR)和胶囊浓缩剂(CS);这些和其他可能的制剂类型例如由国际作物生命组织(Crop Life International)记载于以下文献中:农药说明书(Pesticide Specifications)、联合国粮农组织和世界卫生组织农药说明书开发与使用手册(Manual on development and use of FAO and WHO specifications forpesticides)、联合国粮农组织植物生产与保护文献-173(FAO Plant Production andProtection Papers–173)(由联合国粮农组织/世界卫生组织关于农药说明书的联合会议制订,2004,ISBN:9251048576)。除一种或多种式(I)的化合物外,所述制剂还任选地包含其他农业化学活性成分。
优选包含下述物质的制剂或使用形式:助剂,例如增量剂、溶剂、自发性促进剂、载体、乳化剂、分散剂、防冻剂、杀生物剂、增稠剂;和/或其他助剂,例如佐剂。在本文中,佐剂为增强制剂的生物效应的组分,而该组分本身不具有任何生物效应。佐剂的实例为促进保持、铺展、附着到叶子表面或渗透的试剂。
这些制剂以已知的方式制备,例如通过将式(I)的化合物与助剂混合,所述助剂为例如增量剂、溶剂和/或固体载体和/或其他助剂如表面活性剂。所述制剂要么在合适的设施中生产,要么在施用之前或施用过程中制备。
使用的助剂可为适合于将特定的特性(如某些物理、工业和/或生物特性)赋予式(I)的化合物的制剂或由这些制剂制得的使用形式(例如即用型农药,如喷液或拌种产品)的物质。
合适的增量剂为例如水、极性和非极性有机化学液体,例如芳族和非芳族烃(如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(如果合适,其还可被取代、醚化和/或酯化)、酮(如丙酮、环己酮)、酯(包括脂肪和油)和(聚)醚、简单的和取代的胺、酰胺、内酰胺(如N-烷基吡咯烷酮)以及内酯、砜和亚砜(如二甲基亚砜)。
如果使用的增量剂为水,则还可使用例如有机溶剂作为助溶剂。液体溶剂主要为:芳族化合物,如二甲苯、甲苯或烷基萘;氯代芳族烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或石蜡,例如矿物油馏分;矿物油和植物油;醇,如丁醇或乙二醇以及它们的醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜,以及水。
原则上,可以使用所有合适的溶剂。合适的溶剂的实例为芳族烃,如二甲苯、甲苯或烷基萘;氯代芳族烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷、石蜡、矿物油馏分;矿物油和植物油;醇,如甲醇、乙醇、异丙醇、丁醇或乙二醇,以及它们的醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基亚砜,以及水。
原则上,可以使用所有合适的载体。可用的载体尤其包括:例如,铵盐和粉碎的天然矿物,如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土;和粉碎的合成矿物,如细分散的二氧化硅、氧化铝和天然或合成的硅酸盐、树脂、蜡和/或固体肥料。同样可使用所述载体的混合物。可用的用于颗粒剂的载体包括:例如粉碎并分级的天然岩石,如方解石、大理石、浮石、海泡石、白云石;和无机和有机粉的合成颗粒;以及有机材料的颗粒,如锯屑、纸、椰壳、玉米穗轴和烟草秆。
还可使用液化的气态增量剂或溶剂。特别合适的是在标准温度和大气压力下为气态的那些增量剂或载体,例如气溶胶推进剂,如卤代烃,以及丁烷、丙烷、氮气和二氧化碳。
具有离子或非离子特性的乳化剂和/或发泡剂、分散剂或润湿剂或这些表面活性物质的混合物的实例为:聚丙烯酸的盐;木素磺酸的盐;苯酚磺酸的盐或萘磺酸的盐;环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺、与取代的酚(优选烷基酚或芳基酚)的缩聚物;磺基琥珀酸酯的盐;牛磺酸衍生物(优选牛磺酸烷基酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯;以及含有硫酸酯、磺酸酯和磷酸酯的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、蛋白质水解物、木素亚硫酸盐废液和甲基纤维素。如果式(I)的化合物之一和/或惰性载体之一不溶于水并且当施用是在水中进行时,则表面活性剂的存在是有利的。
可存在于制剂及由其获得的使用形式中的其他助剂为染料,例如无机颜料如氧化铁、氧化钛和普鲁士蓝,和有机染料如茜素染料、偶氮染料和金属酞菁染料;以及营养素和痕量营养素,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
可存在的其他组分为稳定剂,例如低温稳定剂、防腐剂、抗氧化剂、光稳定剂或改进化学和/或物理稳定性的其他试剂。还可存在发泡剂(foam generator)或消泡剂。
此外,所述制剂和由其获得的使用形式还可包含以下物质作为另外的助剂:粘着剂(sticker),例如羧甲基纤维素以及粉末、颗粒或胶乳形式的天然和合成聚合物(如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯),或天然磷脂如脑磷脂和卵磷脂,以及合成磷脂。其他助剂可为矿物油和植物油。
如果合适,所述制剂和由其获得的使用形式中还可存在其他助剂。这样的添加剂的实例为香料、保护性胶体、粘结剂、粘合剂、增稠剂、触变剂、渗透剂、保持促进剂、稳定剂、螯合剂、络合剂、保湿剂、展着剂。通常,式(I)的化合物可与常用于制剂目的的任何固体或液体添加剂结合。
可用的保持促进剂包括降低动态表面张力的所有那些物质,例如磺基琥珀酸二辛酯;或提高粘弹性的所有那些物质,例如羟丙基瓜尔胶聚合物。
在本文中,可用的渗透剂为常用于提高农业化学活性化合物向植物渗透的所有那些物质。在本文中,渗透剂通过以下来定义:其从(通常为水性的)施用液体和/或从喷雾涂层向植物的表皮渗透从而增加活性成分在表皮中的迁移性的能力。可使用文献(Baur等人,1997,Pesticide Science51,131-152)中记载的方法来测定此特性。实例包括醇烷氧基化物,如椰子脂肪乙氧基化物(10)或异十三烷基乙氧基化物(12);脂肪酸酯,例如菜籽油甲酯或大豆油甲酯;脂肪胺烷氧基化物,例如牛脂胺乙氧基化物(15);或铵盐和/或鏻盐,例如硫酸铵或磷酸氢二铵。
所述制剂优选包含0.00000001重量%至98重量%的式(I)的化合物,更优选0.01重量%至95重量%的式(I)的化合物,最优选0.5重量%至90重量%的式(I)的化合物,基于制剂的重量计。
在由所述制剂制得的使用形式(特别是农药)中,式(I)的化合物的含量可在宽范围内变化。在使用形式中,式(I)的化合物的浓度通常可为0.00000001重量%至95重量%的式(I)的化合物,优选0.00001重量%至1重量%,基于使用形式的重量计。施用以适合于使用形式的常规方式完成。
混合物
式(I)的化合物还可与一种或多种合适的以下物质以混合物的形式使用:杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物试剂、有益生物、除草剂、肥料、驱鸟剂、phytotonics、止繁殖剂、安全剂、化学信息素和/或植物生长调节剂,从而由此例如拓宽作用谱、延长作用时间、提高作用速率、防止排斥或防止抗性的发展。此外,这类活性成分结合物可改善植物生长和/或对非生物因素(例如高温或低温、干旱或高的水含量或土壤盐度)的耐受性。还可以改善开花和结果性能、优化发芽能力和根发育、促进采收并提高产量、影响成熟、提高采收产品的品质和/或营养价值、延长采收产品的储存期和/或提高其加工性。
此外,式(I)的化合物可以与其他活性成分或化学信息素(如引诱剂和/或驱鸟剂和/或植物激活剂和/或生长调节剂和/或肥料)以混合物的形式存在。同样,式(I)的化合物可以与改善植物特性例如生长、采收物的产量和品质的试剂的混合物的形式使用。
在本发明的一个具体的实施方案中,在制剂或由这些制剂制备的使用形式中,式(I)的化合物以与其他化合物、优选下文所述的那些化合物的混合物的形式存在。
如果下述化合物之一可以不同的互变异构形式存在,则在每种情况下还包括这些形式,即使没有明确提及。
杀昆虫剂/杀螨剂/杀线虫剂
本文中以通用名称说明的活性成分是已知的,并且记载于例如《农药手册》(“ThePesticide Manual”),第16版,British Crop Protection Council 2012中或可在互联网(例如http://www.alanwood.net/pesticides)上检索到。
(1)乙酰胆碱酯酶(AChE)抑制剂,例如氨基甲酸酯类,例如棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、甲萘威(carbaryl)、克百威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、甲硫威(methiocarb)、灭多威(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC和灭杀威(xylylcarb);或有机磷酸酯类,例如乙酰甲胺磷(acephate)、甲基吡啶磷(azamethiphos)、益棉磷(azinphos-ethyl)、保棉磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、毒死蜱(chloropyrifos)、甲基毒死蜱(chloropyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪磷(diazinon)、敌敌畏/DDVP(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟硫磷(fenitrothion)、倍硫磷(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、imicyafos、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯(isopropyl O-(methoxyaminothiophosphoryl)salicylate)、噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、对硫磷(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、辛硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion);
(2)GABA门控氯化物通道拮抗剂,例如环戊二烯有机氯类,例如氯丹(chlordane)和硫丹(endosulfan);或苯基吡唑类(fiproles),例如乙虫腈(ethiprole)和氟虫腈(fipronil);
(3)钠通道调节剂/电压门控钠通道阻断剂,例如拟除虫菊酯(pyrethroid)类,例如氟丙菊酯(acrinathrin)、烯丙菊酯(allethrin)、d-顺-反烯丙菊酯(d-cis-transallethrin)、d-反烯丙菊酯(d-trans allethrin)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯S-环戊烯基异构体、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、氟氯氰菊酯(cyhalothrin)、λ-氟氯氰菊酯(lambda-cyhalothrin)、γ-氟氯氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、β-氯氰菊酯(beta-cypermethrin)、θ-氯氰菊酯(theta-cypermethrin)、ζ-氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-trans isomers])、溴氰菊酯(deltamethrin)、烯炔菊酯[(EZ)-(1R)异构体](empenthrin[(EZ)-(1R)isomers])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、苄氯菊酯(permethrin)、苯醚菊酯((1R)-反式异构体)(phenothrin[(1R)-trans isomer])、炔丙菊酯(prallethrin)、除虫菊酯(除虫菊)(pyrethrins(pyrethrum))、灭虫菊(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(1R)异构体)]、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin);或DDT;或甲氧氯(methoxychlor);
(4)烟碱型(Nicotinergic)乙酰胆碱受体(nAChR)激动剂,例如新烟碱类(neonicotinoids),例如啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam);或烟碱(nicotine);或氟啶虫胺腈(sulfoxaflor);或氟吡呋喃酮(flupyradifurone);
(5)烟碱乙酰胆碱受体(nAChR)变构激活剂,例如多杀菌素类(spinosyns),例如乙基多杀菌素(spinetoram)和多杀菌素(spinosad);
(6)氯化物通道激活剂,例如阿维菌素类(avermectins)/米尔倍霉素类(milbemycins),例如阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectinbenzoate)、雷皮菌素(lepimectin)和弥拜菌素(milbemectin);
(7)保幼激素模拟物,例如保幼激素类似物,例如烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)和烯虫酯(methoprene);或苯氧威(fenoxycarb);或吡丙醚(pyriproxyfen);
(8)具有未知的或不明确的作用机理的活性成分,例如
卤代烷,例如溴代甲烷和其他卤代烷;或氯化苦(chloropicrine);或硫酰氟(sulfurylfluoride);或硼砂;或吐酒石;
(9)选择性拒食剂,例如吡蚜酮(pymetrozine);或氟啶虫酰胺(flonicamid);
(10)螨生长抑制剂,例如四螨嗪(clofentezine)、噻螨酮(hexythiazox)和氟螨嗪(diflovidazin);或乙螨唑(etoxazole);
(11)昆虫肠膜微生物干扰剂,例如苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis),以及BT植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1;
(12)氧化磷酸化抑制剂、ATP干扰剂,例如丁醚脲(diafenthiuron);或有机锡化合物,例如三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatin oxide);或克螨特(propargite);或四氯杀螨砜(tetradifon);
(13)间断H质子梯度的氧化磷酸化解偶联剂,例如虫螨腈(chlorfenapyr)、DNOC和氟虫胺(sulfluramid);
(14)烟碱乙酰胆碱受体拮抗剂,例如杀虫磺(bensultap)、杀螟丹盐酸盐(cartaphydrochloride)、杀虫环(thiocyclam)和杀虫双(thiosultap-sodium);
(15)几丁质生物合成抑制剂,0型,例如双三氟虫脲(bistrifluron)、定虫隆(chlofluazuron)、除虫脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀虫隆(triflumuron);
(16)几丁质生物合成抑制剂,1型,例如,例如噻嗪酮(buprofezin);
(17)蜕皮干扰剂(尤其是针对双翅目,即双翅类昆虫),例如灭蝇胺(cyromazine);
(18)蜕皮激素受体激动剂,例如环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide);
(19)章鱼胺能激动剂,例如双甲脒(amitraz);
(20)复合物-III电子转移抑制剂,例如氟蚁腙(hydramethylnon)或灭螨醌(acequinocyl)或嘧螨酯(fluacrypyrim);
(21)复合物-I电子转移抑制剂,例如METI杀螨剂,例如喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)和唑虫酰胺(tolfenpyrad),或鱼藤酮(rotenone)(鱼藤属(Derris));
(22)电压门控钠通道阻断剂,例如茚虫威(indoxacarb)或氰氟虫胺(metaflumizone);
(23)乙酰基-CoA羧化酶抑制剂,例如特窗酸和特特拉姆酸衍生物,例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat);
(24)复合物-IV电子转移抑制剂,例如膦类化合物,如磷化铝、磷化钙、膦和磷化锌;或氰化物;
(25)复合物-II电子转移抑制剂,例如腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen);
(28)兰尼碱(ryanodine)受体效应物,例如二酰胺,如氯虫苯甲酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)和氟虫双酰胺(flubendiamide);
作用机理未知或不确定的其他活性化合物,例如afidopyropen、阿福拉纳(afoxolaner)、印楝素(azadirachtin)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、broflanilide、溴螨酯(bromopropylate)、灭螨猛(quinomethionate)、冰晶石(cryolite)、环溴虫酰胺(cyclaniliprole)、环氧虫啶(cycloxaprid)、氯氟氰虫酰胺(cyhalodiamide)、dicloromezotiaz、三氯杀螨醇(dicofol)、氟螨嗪(diflovidazin)、flometoquin、fluazaindolizine、氟噻虫砜(fluensulfone)、嘧虫胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、丁烯氟虫腈(flufiprole)、fluhexafon、氟吡菌酰胺(fluopyram)、氟雷拉纳(fluralaner)、fluxametamide、呋喃虫酰肼(fufenozide)、戊吡虫胍(Guadipyr)、heptafluthrin、氯噻啉(imidaclothiz)、异菌脲(iprodione)、lotilaner、氯氟醚菊酯(meperfluthrin)、哌虫啶(paichongding)、pyflubumide、啶虫丙醚(pyridalyl)、pyrifluquinazon、嘧螨胺(pyriminostrobin)、sarolaner、四氟醚菊酯(tetramethylfluthrin)、氟氰虫酰胺(tetraniliprole)、氯虫苯甲酰胺(tetrachlorantraniliprole)、tioxazafen、thiofluoximate、triflumezopyrim和碘甲烷(iodomethane);以及另外基于坚强芽孢杆菌(Bacillus firmus)(I-1582,BioNeem,Votivo)的制剂,和以下已知的活性化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(已知于WO2006/043635)、{1'-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]-5-氟螺[吲哚-3,4'-哌啶]-1(2H)-基}(2-氯吡啶-4-基)甲酮(已知于WO2003/106457)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]异烟酰胺(已知于WO2006/003494)、3-(2,5-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(已知于WO2009/049851)、3-(2,5-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基碳酸乙酯(已知于WO2009/049851)、4-(丁-2-炔-1-基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(已知于WO2004/099160)、4-(丁-2-炔-1-基氧基)-6-(3-氯苯基)嘧啶(已知于WO2003/076415)、PF1364(CAS登记号1204776-60-2)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氯-3-甲基苯甲酰基]-2-甲基肼甲羧酸甲酯(已知于WO2005/085216)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氰基-3-甲基苯甲酰基]-2-乙基肼甲羧酸甲酯(已知于WO2005/085216)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氰基-3-甲基苯甲酰基]-2-甲基肼甲羧酸甲酯(已知于WO2005/085216)、2-[3,5-二溴-2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)苯甲酰基]-2-乙基肼甲羧酸甲酯(已知于WO2005/085216)、N-[2-(5-氨基-1,3,4-噻二唑-2-基)-4-氯-6-甲基苯基]-3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺(已知于CN102057925)、4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4,5-二氢-1,2-噁唑-3-基]-2-甲基-N-(1-氧化硫杂环丁烷(oxidothietan)-3-基)苯甲酰胺(已知于WO2009/080250)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(已知于WO2012/029672)、1-[(2-氯-1,3-噻唑-5-基)甲基]-4-氧代-3-苯基-4H-吡啶并[1,2-a]嘧啶-1-鎓-2-醇化物(已知于WO2009/099929)、1-[(6-氯吡啶-3-基)甲基]-4-氧代-3-苯基-4H-吡啶并[1,2-a]嘧啶-1-鎓-2-醇化物(已知于WO2009/099929)、4-(3-{2,6-二氯-4-[(3,3-二氯丙-2-烯-1-基)氧基]苯氧基}丙氧基)-2-甲氧基-6-(三氟甲基)嘧啶(已知于CN101337940)、N-[2-(叔丁基氨基甲酰基)-4-氯-6-甲基苯基]-1-(3-氯吡啶-2-基)-3-(氟甲氧基)-1H-吡唑-5-甲酰胺(已知于WO2008/134969)、[2-(2,4-二氯苯基)-3-氧代-4-氧杂螺[4.5]癸-1-烯-1-基]碳酸丁酯(已知于CN 102060818)、3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-1,1,1-三氟丙-2-酮(已知于WO2013/144213)、N-(甲基磺酰基)-6-[2-(吡啶-3-基)-1,3-噻唑-5-基]吡啶-2-甲酰胺(已知于WO2012/000896)、N-[3-(苄基氨基甲酰基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-羧酰胺(已知于WO2010/051926)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基氨基甲酰基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲酰胺(已知于CN103232431)。
杀真菌剂
本文中以通用名称说明的活性成分是已知的,并且记载于例如《农药手册》中或互联网(例如:http://www.alanwood.net/pesticides)上。
如果存在合适的官能团,则在(1)至(15)类中列出的所有杀真菌混合组分可任选地与相应的碱或酸形成盐。此外,如果互变异构是可行的,则(1)至(15)类中列出的杀真菌混合组分也包括互变异构形式。
1)麦角固醇生物合成抑制剂,例如(1.01)4-十二烷基-2,6-二甲基吗啉(aldimorph)、(1.02)阿扎康唑(azaconazole)、(1.03)双苯三唑醇(bitertanol)、(1.04)糠菌唑(bromuconazole)、(1.05)环唑醇(cyproconazole)、(1.06)苄氯三唑醇(diclobutrazole)、(1.07)苯醚甲环唑(difenoconazole)、(1.08)烯唑醇(diniconazole)、(1.09)烯唑醇(diniconazole-M)、(1.10)十二环吗啉(dodemorph)、(1.11)十二环吗啉乙酸盐(dodemorphacetate)、(1.12)氟环唑(epoxiconazole)、(1.13)乙环唑(etaconazole)、(1.14)氯苯嘧啶醇(fenarimol)、(1.15)腈苯唑(fenbuconazole)、(1.16)环酰菌胺(fenhexamide)、(1.17)苯锈啶(fenpropidin)、(1.18)丁苯吗啉(fenpropimorph)、(1.19)氟喹唑(fluquinconazole)、(1.20)呋嘧醇(flurprimidol)、(1.21)氟硅唑(flusilazole)、(1.22)粉唑醇(flutriafol)、(1.23)呋菌唑(furconazole)、(1.24)呋醚唑(furconazole-cis)、(1.25)己唑醇(hexaconazole)、(1.26)抑霉唑(imazalil)、(1.27)烯菌灵硫酸盐(imazalilsulphate)、(1.28)亚胺唑(imibenconazole)、(1.29)种菌唑(ipconazole)、(1.30)叶菌唑(metconazole)、(1.31)腈菌唑(myclobutanil)、(1.32)萘替芬(naftifine)、(1.33)氟苯嘧啶醇(nuarimol)、(1.34)噁咪唑(oxpoconazole)、(1.35)多效唑(paclobutrazole)、(1.36)稻瘟酯(pefurazoate)、(1.37)戊菌唑(penconazole)、(1.38)粉病灵(piperalin)、(1.39)咪鲜胺(prochloraz)、(1.40)丙环唑(propiconazole)、(1.41)丙硫菌唑(prothioconazole)、(1.42)稗草丹(pyributicarb)、(1.43)啶斑肟(pyrifenox)、(1.44)唑喹菌酮(quinconazole)、(1.45)硅氟唑(simeconazole)、(1.46)螺环菌胺(spiroxamine)、(1.47)戊唑醇(tebuconazole)、(1.48)特比萘芬(terbinafin)、(1.49)四氟醚唑(tetraconazole)、(1.50)三唑酮(triadimefon)、(1.51)唑菌醇(triadimenol)、(1.52)十三吗啉(tridemorph)、(1.53)氟菌唑(triflumizole)、(1.54)嗪氨灵(triforin)、(1.55)灭菌唑(triticonazole)、(1.56)烯效唑(uniconazole)、(1.57)精烯效唑(uniconazole-p)、(1.58)烯霜苄唑(viniconazole)、(1.59)伏立康唑(voriconazole)、(1.60)1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、(1.61)1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯、(1.62)N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基亚氨基甲酰胺、(1.63)N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}亚氨基甲酰胺、(1.64)O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]1H-咪唑-1-硫代甲酸酯(carbothioate)、(1.65)啶菌噁唑(pyrisoxazole)、(1.66)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.67)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.68)5-(烯丙基硫烷基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.69)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.70)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.71)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.72)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.73)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.74)5-(烯丙基硫烷基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.75)5-(烯丙基硫烷基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.76)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.77)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.78)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.79)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.80)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.81)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.82)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.83)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.84)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.85)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.86)2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)戊-2-醇、(1.87)2-[2-氯-4-(4-氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.88)2-[2-氯-4-(2,4-二氯苯氧基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.89)(2R)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.90)(2R)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.91)(2S)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.92)(2S)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.93)(1S,2R,5R)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.94)(1R,2S,5S)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.95)5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇;
2)呼吸链复合物I或II抑制剂,例如(2.01)联苯吡菌胺(bixafen)、(2.02)啶酰菌胺(boscalid)、(2.03)萎锈灵(carboxin)、(2.04)氟嘧菌胺(diflumetorim)、(2.05)甲呋酰胺(fenfuram)、(2.06)氟吡菌酰胺(fluopyram)、(2.07)氟酰胺(flutolanil)、(2.08)氟唑菌酰胺(fluxapyroxad)、(2.09)呋吡菌胺(furametpyr)、(2.10)拌种胺(furmecyclox)、(2.11)吡唑萘菌胺(isopyrazam)(顺式差向异构外消旋体1RS、4SR、9RS与反式差向异构外消旋体1RS,4SR,9SR的混合物)、(2.12)吡唑萘菌胺(反式差向异构外消旋体1RS,4SR,9SR)、(2.13)吡唑萘菌胺(反式差向异构对映体1R,4S,9S)、(2.14)吡唑萘菌胺(反式差向异构对映体1S,4R,9R)、(2.15)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.16)吡唑萘菌胺(顺式差向异构对映体1R,4S,9R)、(2.17)吡唑萘菌胺(顺式差向异构对映体1S,4R,9S)、(2.18)灭锈胺(mepronil)、(2.19)氧化萎锈灵(oxycarboxin)、(2.20)戊苯吡菌胺(penflufen)、(2.21)吡噻菌胺(penthiopyrad)、(2.22)氟唑环菌胺(sedaxane)、(2.23)噻氟菌胺(thifluzamide)、(2.24)1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(2.25)3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、(2.26)3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、(2.27)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.28)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.29)苯并烯氟菌唑(benzovindiflupyr)、(2.30)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘(methanonaphthalen)-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.31)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.32)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.33)1,3,5-三甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.34)1-甲基-3-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.35)1-甲基-3-(三氟甲基)-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.36)1-甲基-3-(三氟甲基)-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.37)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.38)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.39)1,3,5-三甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.40)1,3,5-三甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.41)麦锈灵(benodanil)、(2.42)2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、(2.43)isofetamide、(2.44)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.45)N-(4'-氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.46)N-(2',4'-二氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.47)3-(二氟甲基)-1-甲基-N-[4'-(三氟甲基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.48)N-(2',5'-二氟联苯-2-基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(2.49)3-(二氟甲基)-1-甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.50)5-氟-1,3-二甲基-N-[4'-(丙-1-炔-1-基)联苯-2-基]-1H-吡唑-4-甲酰胺、(2.51)2-氯-N-[4'-(丙-1-炔-1-基)联苯-2-基]烟酰胺、(2.52)3-(二氟甲基)-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.53)N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、(2.54)3-(二氟甲基)-N-(4'-乙炔基联苯-2-基)-1-甲基-1H-吡唑-4-甲酰胺、(2.55)N-(4'-乙炔基联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、(2.56)2-氯-N-(4'-乙炔基联苯-2-基)烟酰胺、(2.57)2-氯-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(2.58)4-(二氟甲基)-2-甲基-N-[4'-(三氟甲基)联苯-2-基]-1,3-噻唑-5-甲酰胺、(2.59)5-氟-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、(2.60)2-氯-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(2.61)3-(二氟甲基)-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.62)5-氟-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]-1,3-二甲基-1H-吡唑-4-甲酰胺、(2.63)2-氯-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(2.64)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.65)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.66)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.67)3-(二氟甲基)-N-甲氧基-1-甲基-N-[1-(2,4,6-三氯苯基)丙-2-基]-1H-吡唑-4-甲酰胺、(2.68)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲酰胺、(2.69)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.70)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺;
3)呼吸链复合物III抑制剂,例如(3.01)唑嘧菌胺(ametoctradin)、(3.02)吲唑磺菌胺(amisulbrom)、(3.03)嘧菌酯(azoxystrobin)、(3.04)氰霜唑(cyazofamid)、(3.05)甲香菌酯(coumethoxystrobin)、(3.06)丁香菌酯(coumoxystrobin)、(3.07)醚菌胺(dimoxystrobin)、(3.08)enoxastrobin、(3.09)噁唑菌酮(famoxadon)、(3.10)咪唑菌酮(fenamidon)、(3.11)氟菌螨酯(flufenoxystrobin)、(3.12)氟嘧菌酯(fluoxastrobin)、(3.13)醚菌酯(kresoxim-methyl)、(3.14)苯氧菌胺(metominostrobin)、(3.15)肟醚菌胺(orysastrobin)、(3.16)啶氧菌酯(picoxystrobin)、(3.17)唑菌胺酯(pyraclostrobin)、(3.18)唑胺菌酯(pyrametostrobin)、(3.19)唑菌酯(pyraoxystrobin)、(3.20)吡菌苯威(pyribencarb)、(3.21)氯啶菌酯(triclopyricarb)、(3.22)肟菌酯(trifloxystrobin)、(3.23)(2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.24)(2E)-2-(甲氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺、(3.25)(2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺、(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.27)fenaminostrobin、(3.28)5-甲氧基-2-甲基-4-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)-2,4-二氢-3H-1,2,4-三唑-3-酮、(3.29)(2E)-2-{2-[({环丙基[(4-甲氧基苯基)亚氨基]甲基}硫烷基)甲基]苯基}-3-甲氧基丙烯酸甲酯、(3.30)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰胺基-2-羟基苯甲酰胺、(3.31)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.32)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.33)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基五-3-烯酰胺;
4)有丝分裂和细胞分裂抑制剂,例如(4.01)苯菌灵(benomyl)、(4.02)多菌灵(carbendazim)、(4.03)苯咪唑菌(chlorfenazole)、(4.04)乙霉威(diethofencarb)、(4.05)噻唑菌胺(ethaboxam)、(4.06)氟啶酰菌胺(fluopicolide)、(4.07)麦穗宁(fuberidazole)、(4.08)戊菌隆(pencycuron)、(4.09)噻菌灵(thiabendazole)、(4.10)甲基硫菌灵(thiophanate-methyl)、(4.11)硫菌灵(thiophanate)、(4.12)苯酰菌胺(zoxamide)、(4.13)5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶、(4.14)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪;
5)具有多位点作用的化合物,例如(5.01)波尔多混合液(Bordeaux mixture)、(5.02)敌菌丹(captafol)、(5.03)克菌丹(captan)、(5.04)百菌清(chlorothalonil)、(5.05)氢氧化铜、(5.06)环烷酸铜、(5.07)氧化铜、(5.08)氯氧化铜(copper oxychloride)、(5.09)硫酸铜(2+)、(5.10)抑菌灵(dichlofluanid)、(5.11)二氰蒽醌(dithianon)、(5.12)多果定(dodine)、(5.13)多果定游离碱(dodine free base)、(5.14)福美铁(ferbam)、(5.15)fluorofolpet、(5.16)灭菌丹(folpet)、(5.17)双胍辛盐(guazatine)、(5.18)双胍辛乙酸盐(guazatine acetate)、(5.19)双胍辛胺(iminoctadine)、(5.20)双胍辛胺苯磺酸盐(iminoctadine albesilate)、(5.21)双胍辛胺三乙酸盐(iminoctadine triacetate)、(5.22)代森锰铜(mancopper)、(5.23)代森锰锌(mancozeb)、(5.24)代森锰(maneb)、(5.25)代森联(metiram)、(5.26)代森联锌(metiram zinc)、(5.27)喹啉铜(oxine-copper)、(5.28)丙烷脒(propamidine)、(5.29)丙森锌(propineb)、(5.30)包括多硫化钙(calciumpolysulfide)的硫和硫制品、(5.31)福美双(thiram)、(5.32)甲苯氟磺胺(tolylfluanid)、(5.33)代森锌(zineb)、(5.34)福美锌(ziram)、(5.35)敌菌灵(anilazine);
6)能够诱导寄主防御的化合物,例如(6.01)苯并噻二唑(acibenzolar-S-methyl)、(6.02)异噻菌胺(isotianil)、(6.03)烯丙苯噻唑(probenazole)、(6.04)噻酰菌胺(tiadinil)、(6.05)海带多糖(laminarin);
7)氨基酸和/或蛋白质生物合成抑制剂,例如(7.01)andoprim、(7.02)灭瘟素(blasticidin-S)、(7.03)嘧菌环胺(cyprodinil)、(7.04)春雷霉素(kasug amycin)、(7.05)春雷霉素盐酸盐水合物(kasugamycin hydrochloride hydrate)、(7.06)嘧菌胺(mepanipyrim)、(7.07)嘧霉胺(pyrimethanil)、(7.08)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉、(7.09)氧四环素(oxytetracycline)、(7.10)链霉素(streptomycin);
8)ATP产生抑制剂,例如(8.01)三苯基乙酸锡(fentin acetate)、(8.02)三苯基氯化锡(fentin chloride)、(8.03)毒菌锡(fentin hydroxide)、(8.04)硅噻菌胺(silthiofam);
9)细胞壁合成抑制剂,例如(9.01)苯噻菌胺(benthiavalicarb)、(9.02)烯酰吗啉(dimethomorph)、(9.03)氟吗啉(flumorph)、(9.04)异丙菌胺(iprovalicarb)、(9.05)双炔酰菌胺(mandipropamide)、(9.06)多抗霉素(polyoxins)、(9.07)多氧霉素(polyoxorim)、(9.08)有效霉素A(validamycin A)、(9.09)霜霉灭(valifenalate)、(9.10)多氧菌素B(polyoxin B)、(9.11)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(9.12)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮;
10)脂质和膜合成抑制剂,例如(10.01)联苯、(10.02)地茂散(chloroneb)、(10.03)氯硝胺(dicloran)、(10.04)敌瘟磷(edifenphos)、(10.05)土菌灵(etridiazole)、(10.06)碘代丙炔基丁基甲胺酸酯(iodocarb)、(10.07)异稻瘟净(iprobenfos)、(10.08)稻瘟灵(isoprothiolane)、(10.09)霜霉威(propamocarb)、(10.10)霜霉威盐酸盐(propamocarbhydrochloride)、(10.11)硫菌威(prothiocarb)、(10.12)吡菌磷(pyrazophos)、(10.13)五氯硝基苯(quintozene)、(10.14)四氯硝基苯(tecnazene)、(10.15)甲基立枯磷(tolclofos-methyl);
11)黑色素生物合成抑制剂,例如(11.01)环丙酰菌胺(capropamide)、(11.02)双氯氰菌胺(diclocymet)、(11.03)氰菌胺(fenoxanil)、(11.04)四氯苯酞(phthalide)、(11.05)咯喹酮(pyroquilon)、(11.06)三环唑(tricyclazole)、(11.07)2,2,2-三氟乙基{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸酯;
12)核酸合成抑制剂,例如(12.01)苯霜灵(benalaxyl)、(12.02)精苯霜灵(benalaxyl-M)(kiralaxyl)、(12.03)乙嘧酚磺酸酯(bupirimate)、(12.04)clozylacon、(12.05)二甲嘧酚(dimethirimol)、(12.06)乙嘧酚(ethirimol)、(12.07)呋霜灵(furalaxyl)、(12.08)噁霉灵(hymexazol)、(12.09)甲霜灵(metalaxyl)、(12.10)高效甲霜灵(精甲霜灵)((metalaxyl-M)(mefenoxam))、(12.11)呋酰胺(ofurace)、(12.12)噁霜灵(oxadixyl)、(12.13)噁喹酸(oxolinic acid)、(12.14)辛噻酮(octhilinone);
13)信号转导抑制剂,例如(13.01)乙菌利(chlozolinate)、(13.02)拌种咯(fenpiclonil)、(13.03)咯菌腈(fludioxonil)、(13.04)异菌脲(iprodione)、(13.05)腐霉利(procymidone)、(13.06)苯氧喹啉(quinoxyfen)、(13.07)乙烯菌核利(vinclozolin)、(13.08)丙氧喹啉(proquinazid);
14)能用作解偶联剂的化合物,例如(14.01)乐杀螨(binapacryl)、(14.02)敌螨普(dinocap)、(14.03)嘧菌腙(ferimzone)、(14.04)氟啶胺(fluazinam)、(14.05)消螨多(meptyldinocap);
15)其他化合物,例如(15.001)苯噻硫氰(benthiazole)、(15.002)bethoxazin、(15.003)卡巴西霉素(capsimycin)、(15.004)香芹酮(carvone)、(15.005)灭螨猛(quinomethionate)、(15.006)pyriofenone(氯芬酮(chlazafenone))、(15.007)硫杂灵(cufraneb)、(15.008)环氟菌胺(cyflufenamid)、(15.009)霜脲氰(cymoxanil)、(15.010)啶酰菌胺(cyprosulfamide)、(15.011)棉隆(dazomet)、(15.012)咪菌威(debacarb)、(15.013)双氯酚(dichlorophen)、(15.014)哒菌清(diclomezin)、(15.015)野燕枯(difenzoquat)、(15.016)野燕枯甲基硫酸酯(difenzoquat metilsulfate)、(15.017)二苯胺(diphenylamine)、(15.018)ecomate、(15.019)胺苯吡菌酮(fenpyrazamine)、(15.020)氟酰菌胺(flumetover)、(15.021)氟酰亚胺(fluoroimide)、(15.022)磺菌胺(flusulfamide)、(15.023)flutianil、(15.024)三乙膦酸铝(fosetyl-aluminium)、(15.025)三乙膦酸钙(fosetyl-calcium)、(15.026)三乙膦酸钠(fosetyl-sodium)、(15.027)六氯苯(hexachlorobenzene)、(15.028)人间霉素(irumamycin)、(15.029)磺菌威(methasulfocarb)、(15.030)异硫氰酸甲酯(methyl isothiocyanate)、(15.031)苯菌酮(metrafenone)、(15.032)米多霉素(mildiomycin)、(15.033)纳他霉素(natamycin)、(15.034)福美镍(nickel dimethyldithiocarbamate)、(15.035)酞菌酯(nitrothal-isopropyl)、(15.036)oxamocarb、(15.037)oxyfenthiin、(15.038)五氯苯酚(pentachlorophenol)及其盐、(15.039)苯醚菊酯(phenothrin)、(15.040)磷酸及其盐、(15.041)霜霉威乙膦酸盐(propamocarb-fosetylate)、(15.042)propanosine-sodium、(15.043)吡吗啉(Pyrimorph)、(15.044)吡咯尼群(pyrrolnitrin)、(15.045)异丁乙氧喹啉(tebufloquin)、(15.046)叶枯酞(tecloftalam)、(15.047)tolnifanid、(15.048)咪唑嗪(triazoxide)、(15.049)水杨菌胺(trichlamid)、(15.050)氰菌胺(zarilamid)、(15.051)2-甲基丙酸(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧壬-7-基酯、(15.052)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.053)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(15.054)oxathiapiproline、(15.055)1H-咪唑-1-甲酸1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基酯、(15.056)2,3,5,6-四氯-4-(甲基磺酰基)吡啶、(15.057)2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮、(15.058)2,6-二甲基-1H,5H-[1,4]二噻英并[2,3-c:5,6-c']联吡咯-1,3,5,7(2H,6H)-四酮、(15.059)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5R)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、(15.060)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-(4-{4-[(5S)-5-苯基-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)乙酮、(15.061)2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]-1-{4-[4-(5-苯基-4,5-二氢-1,2-噁唑-3-基)-1,3-噻唑-2-基]哌啶-1-基}乙酮、(15.062)2-丁氧基-6-碘-3-丙基-4H-苯并吡喃-4-酮、(15.063)2-氯-5-[2-氯-1-(2,6-二氟-4-甲氧基苯基)-4-甲基-1H-咪唑-5-基]吡啶、(15.064)2-苯基苯酚和盐、(15.065)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.066)3,4,5-三氯吡啶-2,6-二甲酸腈、(15.067)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(15.068)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(15.069)5-氨基-1,3,4-噻二唑-2-硫醇、(15.070)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、(15.071)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.072)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.073)5-甲基-6-辛基[1,2,4]三唑并[1,5-a]嘧啶-7-胺、(15.074)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.075)N'-(4-{[3-(4-氯苄基)-1,2,4-噻二唑-5-基]氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.076)N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.077)N-[(4-氯苯基)(氰基)甲基]-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.078)N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯烟酰胺、(15.079)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、(15.080)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘烟酰胺、(15.081)N-{(E)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.082)N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.083)N'-{4-[(3-叔丁基-4-氰基-1,2-噻唑-5-基)氧基]-2-氯-5-甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(15.084)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-(1,2,3,4-四氢萘-1-基)-1,3-噻唑-4-甲酰胺、(15.085)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1R)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、(15.086)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-[(1S)-1,2,3,4-四氢萘-1-基]-1,3-噻唑-4-甲酰胺、(15.087){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸戊酯、(15.088)吩嗪-1-甲酸、(15.089)喹啉-8-醇、(15.090)喹啉-8-醇硫酸酯(2:1)、(15.091){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁基酯、(15.092)(5-溴-2-甲氧基-4-甲基吡啶-3-基)(2,3,4-三甲氧基-6-甲基苯基)甲酮、(15.093)N-[2-(4-{[3-(4-氯苯基)丙-2-炔-1-基]氧基}-3-甲氧基苯基)乙基]-N2-(甲基磺酰基)缬氨酰胺、(15.094)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.095){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁-3-炔-1-基酯、(15.096)4-氨基-5-氟嘧啶-2-醇(互变异构形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.097)3,4,5-三羟基苯甲酸丙酯、(15.098)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.099)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.100)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-噁唑-4-基](吡啶-3-基)甲醇、(15.101)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(15.102)2-(6-苄基吡啶-2-基)喹唑啉、(15.103)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.104)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.105)脱落酸、(15.106)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亚氨基甲酰胺、(15.107)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.108)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.109)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.110)N'-{5-溴-6-[(顺式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.111)N'-{5-溴-6-[(反式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(15.112)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.113)N-环丙基-N-(2-环丙基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.114)N-(2-叔丁基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.115)N-(5-氯-2-乙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.116)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.117)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.118)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.119)N-环丙基-N-(2-环丙基-5-氟苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.120)N-(2-环戊基-5-氟苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.121)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.122)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.123)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.124)N-环丙基-N-(2-环丙基-5-甲基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.125)N-(2-叔丁基-5-甲基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.126)N-[5-氯-2-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.127)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基]-1H-吡唑-4-甲酰胺、(15.128)N-[2-氯-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.129)N-[3-氯-2-氟-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.130)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.131)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-硫代甲酰胺、(15.132)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.133)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(15.134)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.135)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氢-1,4-苯并氧杂吖庚因、(15.136)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.137)2-{2-[(7,8-二氟-2-甲基喹啉-3-基)氧基]-6-氟苯基}丙-2-醇、(15.138)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.139)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.140)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.141)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.142)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.143)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.144)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.145)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.146)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.147)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.148)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.149)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(15.150)N'-(4-{3-[(二氟甲基)硫烷基]苯氧基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.151)N'-(2,5-二甲基-4-{3-[(1,1,2,2-四氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.152)N'-(2,5-二甲基-4-{3-[(2,2,2-三氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.153)N'-(2,5-二甲基-4-{3-[(2,2,3,3-四氟丙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.154)N'-(2,5-二甲基-4-{3-[(五氟乙基)硫烷基]苯氧基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.155)N'-(4-{[3-(二氟甲氧基)苯基]硫烷基}-2,5-二甲基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.156)N'-(2,5-二甲基-4-{[3-(1,1,2,2-四氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.157)N'-(2,5-二甲基-4-{[3-(2,2,2-三氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.158)N'-(2,5-二甲基-4-{[3-(2,2,3,3-四氟丙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.159)N'-(2,5-二甲基-4-{[3-(五氟乙氧基)苯基]硫烷基}苯基)-N-乙基-N-甲基亚氨基甲酰胺、(15.160)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.161)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.162)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.163)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯基甲磺酸酯、(15.164)2-{3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.165)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5S)-5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.166)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5R)-5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.167)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5S)-5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.168)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5R)-5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.169)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5S)-5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.170)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{(5R)-5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(15.171)2-{(5S)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯基甲磺酸酯、(15.172)2-{(5R)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}苯基甲磺酸酯、(15.173)2-{(5S)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯、(15.174)2-{(5R)-3-[2-(1-{[3,5-二(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基甲磺酸酯。
作为混合组分的生物农药
式(I)的化合物可与生物农药结合。
生物农药尤其包括细菌、真菌、酵母、植物提取物和由微生物形成的产物,包括蛋白质和次级代谢物。
生物农药包括以下细菌:例如,形成孢子的细菌、根部定殖细菌和用作生物杀昆虫剂、杀真菌剂或杀线虫剂的细菌。
用作或可用作生物农药的这类细菌的实例为:
解淀粉芽孢杆菌(Bacillus amyloliquefaciens),菌株FZB42(DSM231179);或蜡样芽孢杆菌(Bacillus cereus),特别是蜡样芽孢杆菌菌株CNCM I-1562;或坚强芽孢杆菌(Bacillus firmus),菌株I-1582(登记号CNCM I-1582);或短小芽孢杆菌(Bacilluspumilus),特别是菌株GB34(登记号ATCC 700814)和菌株QST2808(登记号NRRL B-30087);或枯草芽孢杆菌(Bacillus subtilis),特别是菌株GB03(登记号ATCC SD-1397);或枯草芽孢杆菌菌株QST713(登记号NRRL B-21661)或枯草芽孢杆菌菌株OST30002(登记号NRRL B-50421);苏云金芽孢杆菌(Bacillus thuringiensis),特别是苏云金芽孢杆菌以色列亚种(血清型H-14),菌株AM65-52(登记号ATCC 1276);或苏云金芽孢杆菌鲇泽亚种,特别是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌塔克亚种菌株HD-1,或苏云金芽孢杆菌tenebrionis亚种菌株NB 176(SD-5428);穿刺芽孢杆菌(Pasteuria penetrans);巴斯德氏芽菌属种(Pasteuria spp.)(肾形线虫(Rotylenchulus reniformis nematode))-PR3(登记号ATCC SD-5834);细黄链霉菌(Streptomyces microflavus)菌株AQ6121(=QRD31.013,NRRL B-50550);鲜黄链霉菌(Streptomyces galbus)菌株AQ6047(登记号NRRL 30232)。
用作或可用作生物农药的真菌和酵母的实例是:
球孢白僵菌(Beauveria bassiana),特别是菌株ATCC 74040;盾壳霉(Coniothyriumminitans),特别是菌株CON/M/91-8(登记号DSM-9660);蜡蚧菌属种(Lecanicilliumspp.),特别是菌株HRO LEC12;蜡蚧轮枝菌(Lecanicillium lecanii)(曾用名:Verticillium lecanii),特别是菌株KV01;绿僵菌(Metarhizium anisopliae),特别是菌株F52(DSM3884/ATCC 90448);核果梅奇酵母(Metschnikowia fructicola),特别是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现用名:Isariafumosorosea),特别是菌株IFPC 200613或菌株Apopka97(登记号ATCC 20874);淡紫色拟青霉(Paecilomyces lilacinus),特别是淡紫色拟青霉菌株251(AGAL 89/030550);黄色蠕形霉(Talaromyces flavus),特别是菌株V117b;深绿木霉(Trichoderma atroviride),特别是菌株SC1(登记号CBS 122089);哈茨木霉菌(Trichoderma harzianum),特别是哈茨木霉菌(T.harzianum rifai)T39(登记号CNCM I-952)。
用作或可用作生物农药的病毒的实例是:
棉褐带卷蛾(Adoxophyes orana)(夏季水果卷叶蛾(summer fruit tortrix))微粒子病病毒(GV)、苹果蠹蛾(Cydia pomonella)(codling moth)微粒子病病毒(GV)、棉铃虫(Helicoverpa armigera)(cotton bollworm)核多角体病病毒(NPV)、甜菜夜蛾(Spodoptera exigua)(beet armyworm)mNPV、草地贪夜蛾(Spodoptera frugiperda)(fallarmyworm)mNPV、海灰翅夜蛾(Spodoptera littoralis)(African cotton leafworm)NPV。
还包括作为“接种菌”加入植物或植物部位或植物器官并借助其特殊的性质来促进植物生长和植物健康的细菌和真菌。实例包括:
土壤杆菌属种(Agrobacterium spp.);茎瘤固氮根瘤菌(Azorhizobiumcaulinodans);固氮螺菌属种(Azospirillum spp.);固氮菌属种(Azotobacter spp.);慢生根瘤菌属种(Bradyrhizobium spp.);伯克霍尔德菌属种(Burkholderia spp.),尤其是洋葱伯克霍尔德菌(Burkholderia cepacia)(曾用名:洋葱假单胞菌(Pseudomonascepacia));巨孢囊霉属种(Gigaspora spp.)或单孢巨孢囊霉(Gigaspora monosporum);球囊霉属种(Glomus spp.);蜡蘑属种(Laccaria spp.);布氏乳杆菌(Lactobacillusbuchneri);类球囊霉属种(Paraglomus spp.);Pisolithus tinctorus;假单胞菌属种(Pseudomonas spp.);根瘤菌属种(Rhizobium spp.),尤其是三叶草根瘤菌(Rhizobiumtrifolii);须腹菌属种(Rhizopogon spp.);硬皮马勃属种(Scleroderma spp.);乳牛杆菌属种(Suillus spp.);链霉菌属种(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白质和次级代谢物)的实例为:
大蒜(Allium sativum);苦艾(Artemisia absinthium);印楝素;Biokeeper WP;Cassia nigricans;苦皮藤(Celastrus angulatus);Chenopodium anthelminticum;几丁质(chitin);Armour-Zen;欧洲鳞毛蕨(Dryopteris filix-mas);问荆(Equisetumarvense);Fortune Aza;Fungastop;Heads Up(藜麦皂素(Chenopodium quinoa saponin)提取物);除虫菊/除虫菊素(pyrethrum/pyrethrins);苦木(Quassia amara);栎属(Quercus);皂树(Quillaja);Regalia;“RequiemTM杀昆虫剂”;鱼藤酮(rotenone);鱼尼丁(ryania)/兰尼碱;聚合草(Symphytum officinale);菊蒿(Tanacetum vulgare);百里香酚(thymol);Triact70;TriCon;Tropaeulummajus;大荨麻(Urtica dioica);藜芦碱(Veratrin);白槲寄生(Viscum album);十字花科(Brassicaceae)提取物,尤其是油菜粉或芥末粉。
作为混合组分的安全剂
式(I)的化合物可与安全剂结合,例如与解草嗪(benoxacor)、解草酯(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(CAS 52836-31-4)。
植物和植物部位
可根据本发明处理所有的植物和植物部位。在本文中,植物应理解为意指所有的植物和植物种群,例如需要和不需要的野生植物或作物植物(包括天然存在的作物植物),例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、番茄、柿子辣和红辣椒、黄瓜、甜瓜、胡萝卜、西瓜、洋葱、莴苣、菠菜、韭菜、菜豆、甘蓝(Brassicaoleracea)(例如卷心菜)和其他蔬菜品种、棉花、烟草、油菜以及结果植物(果实为苹果、梨、柑橘类果实和葡萄)。作物植物可为可通过常规育种和优化方法或通过生物技术和基因工程方法或这些方法的结合而获得的植物,包括转基因植物且包括可受和不受植物育种者权利保护的植物栽培种。植物应理解为意指植物的所有发育阶段,例如种子、插条和幼小(未成熟)植物直至成熟植物。植物部位应理解为意指植物的所有地上和地下的部位和器官,例如芽、叶、花及根,实例为叶、针叶、茎、干、花、子实体、果实和种子,以及根、块茎及根茎。植物部位还包括采收材料(采收的植物或植物部位)以及无性和有性繁殖材料,例如插条、块茎、根茎、幼枝(slip)和种子。
根据本发明使用式(I)的化合物对植物和植物部位的处理通过常规处理方法直接进行或使所述化合物作用于其环境、生境或贮存空间来进行,所述常规处理方法为例如浸渍、喷雾、蒸发、弥雾(fogging)、散布(scattering)、涂抹、注入,并且在繁殖材料、特别是在种子的情况下,还通过施加一层或多层包衣来进行。
如上所述,可根据本发明处理所有的植物及其部位。在一个优选的实施方案中,处理野生植物品种和植物栽培种,或通过常规生物育种方法(如杂交或原生质体融合)而得到的那些植物及其部位。在另一个优选的实施方案中,处理通过基因工程方法——如果合适,与常规方法相结合——而得到的转基因植物和植物栽培种(遗传修饰生物体)及其部位。术语“部位”或“植物的部位”或“植物部位”已在上文作出解释。根据本发明特别优选处理相应市售的常规植物栽培种的植物或在使用中的那些植物。植物栽培种应理解为意指通过常规育种、诱变或重组DNA技术生长的具有新特性(“性状”)的植物。它们可以是栽培种、变种、生物型或基因型。
转基因植物、种子处理和整合株系(integration event)
根据本发明处理的优选的转基因植物或植物栽培种(通过基因工程获得的那些植物)包括通过遗传修饰而接受了将特别有利的有用特性(“性状”)赋予这些植物的遗传物质的所有植物。这些特性的实例为更好的植物生长、提高的对高温或低温的耐受性、提高的对干旱或对水或土壤盐度水平的耐受性、增强的开花性能、更容易采收、加速成熟、更高的采收产率、采收产品的品质更高和/或营养价值更高、采收产品的贮存能力和/或加工性更好。这些特性的其他且特别强调的实例为:由于例如在植物内形成的毒素、特别是通过来自苏云金芽孢杆菌的遗传物质(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF以及其组合)在植物内产生的毒素而使植物对动物害虫和微生物害虫(例如昆虫、蛛形纲动物、线虫、螨、蛞蝓和腹足类动物)的抗性提高;以及例如通过系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子(elicitor)和抗性基因以及相应表达的蛋白质和毒素而导致的植物对植物病原性真菌、细菌和/或病毒的抗性提高;以及植物对某些除草活性化合物例如咪唑啉酮、磺酰脲、草甘膦或草丁膦(phosphinothricin)的耐受性提高(例如“PAT”基因)。赋予所述期望特性(“性状”)的基因还可在转基因植物中以相互结合的方式存在。提及的转基因植物的实例包括重要的作物植物,例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、西红柿、豌豆和其他蔬菜品种、棉花、烟草、油菜以及结果植物(果实为苹果、梨、柑橘类果实和葡萄),特别强调的是玉米、大豆、小麦、稻、马铃薯、棉花、甘蔗、烟草和油菜。特别强调的特性(“性状”)为植物对昆虫、蛛形纲动物、线虫以及蛞蝓和腹足类动物的抗性提高。
作物保护——处理的类型
通过使用常规处理方法使用式(I)的化合物对植物和植物部位直接处理或通过作用于其环境、生境或储存空间来处理,所述常规处理方法为,例如浸渍、喷雾、雾化、灌溉、蒸发、撒粉、弥雾、撒播、发泡、涂布、铺展(spreading-on)、注射、浇水(浸透)、滴灌,并且在繁殖材料、特别是种子的情况下,还通过干燥种子处理、液体种子处理、浆料处理,通过形成包壳(incrusting),通过用一层或多层包衣包覆等。还可通过超低容量法施用式(I)的化合物,或将所述施用形式或式(I)的化合物本身注入土壤中。
优选的对植物的直接处理为叶面施用,即将式(I)的化合物施用于叶子,其中应当根据所述害虫的侵染水平来调节处理频率和施用率。
在内吸性活性化合物的情况下,式(I)的化合物还通过根系进入植物。于是,通过将式(I)的化合物作用于植物的生境来处理植物。这可以例如通过以下方式来完成:浸透或混入土壤或营养液中,意指用式(I)的化合物的液体形式浸渍植物的位置(例如土壤或水培体系);或土壤施用,意指将式(I)的化合物以固体形式(例如以颗粒剂的形式)引入植物的位置。在水稻作物的情况下,这还可通过将式(I)的化合物以固体施用形式(例如以颗粒剂的形式)计量加入淹没的(flooded)水稻田中来完成。
种子处理
通过处理植物的种子来防治动物害虫是早就已知的,并且是不断改进的主题。然而,种子处理涉及一系列始终不能以令人满意的方式解决的问题。因此,期望开发保护种子和发芽植物的方法,所述方法在植物的储存过程中、播种后或出苗后免除、或至少显著地减少额外的农药施用。此外,期望优化活性成分的用量,从而为种子和发芽植物提供最佳保护,使其免受动物害虫的侵袭,而使用的活性成分不会损害植物本身。特别地,处理种子的方法还应考虑抵抗或耐受害虫的转基因植物所固有的杀昆虫或杀线虫特性,以便使用最少量的农药实现对种子和发芽植物的最佳保护。
因此,本发明还特别涉及一种通过用式(I)的化合物之一处理种子来保护种子和发芽植物免受害虫侵袭的方法。本发明的保护种子和发芽植物免受害虫侵袭的方法还包括这样的方法:其中,在一次操作中同时用式(I)的化合物和混合组分或者依序用式(I)的化合物和混合组分处理种子。其还进一步包括这样的方法:其中在不同时间用式(I)的化合物和混合组分处理种子。
本发明还涉及式(I)的化合物用于处理种子以保护种子和所得植物免受动物害虫侵袭的用途。
本发明还涉及已用式(I)的化合物处理以保护其免受动物害虫侵袭的种子。本发明还涉及已同时用式(I)的化合物和混合组分处理的种子。本发明还涉及已在不同时间用式(I)的化合物和混合组分处理的种子。对于已在不同时间用式(I)的化合物和混合组分处理的种子,各物质可以不同的层存在于种子上。在此情况下,包含式(I)的化合物和混合组分的层可任选地被中间层隔开。本发明还涉及这样的种子:其中将式(I)的化合物和混合组分作为包衣的一部分或作为除包衣之外的另一层或另几层进行施用。
本发明还涉及这样的种子:在用式(I)的化合物处理之后,对其进行薄膜包衣处理以防止灰尘对种子的磨损。
具有内吸性作用的式(I)的化合物的优点之一在于,通过处理种子,不仅保护种子本身,还保护由其生长的植物在出苗后免受动物害虫的侵袭。以这种方式,可无需在播种时或在播种后不久对作物进行即时处理。
另一优点在于,用式(I)的化合物处理种子可促进经处理的种子的发芽和出苗。
同样认为有利的是,式(I)的化合物还可特别地用于转基因种子。
此外,式(I)的化合物可与信号技术组合物结合使用,从而使得通过共生体(例如根瘤菌、菌根/或植物内生细菌或真菌)而更好地定植和/或优化固氮作用。
式(I)的化合物适合于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。更具体而言,包括以下植物的种子:谷物(例如小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、稻、马铃薯、向日葵、咖啡、烟草、加拿大油菜(canola)、油菜、甜菜(例如糖用甜菜和饲用甜菜)、花生、蔬菜(例如番茄、黄瓜、菜豆、十字花科蔬菜、洋葱和莴苣)、结果植物、草坪和观赏植物。特别有意义的是处理谷物(如小麦、大麦、黑麦和燕麦)、玉米、大豆、棉花、加拿大油菜、油菜、蔬菜和稻的种子。
如上所述,用式(I)的化合物处理转基因种子也是特别重要的。这涉及通常包含至少一种异源基因的植物的种子,所述异源基因控制特别是具有杀昆虫和/或杀线虫特性的多肽的表达。在这种情况下,转基因种子中的异源基因可源自以下微生物:例如,芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单孢菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棒状杆菌属(Clavibacter)、球囊霉属(Glomus)或粘帚霉属(Gliocladium)。本发明特别适用于处理包含至少一种源自芽孢杆菌属种(Bacillussp)的异源基因的转基因种子。所述异源基因更优选源自苏云金芽孢杆菌。
在本发明的上下文中,将(I)的化合物施用于种子。优选在种子稳定得足以在处理过程中不发生损害的状态下处理种子。通常,可在采收和播种之间的任何时间处理种子。通常使用已从植物中分离并且已除去穗轴、外壳、茎、表皮、毛或果肉的种子。因此,例如,可以使用已采收、清洁且干燥至含水量允许储存的种子。或者,还可使用在干燥后用例如水处理然后再干燥(例如灌注(priming))的种子。在稻的种子的情况下,还可以使用例如已经在水中吸胀直至某一阶段(胚乳期(pigeon breast stage))的种子,这改善了发芽情况并使出苗更均匀。
当处理种子时,通常必须注意选择施用于种子的式(I)的化合物的量和/或其他添加剂的量,以使种子的发芽不受到不利影响或所得植物不受到损害。对于在某些施用率下可表现出植物毒性作用的活性成分,必须特别确保这一点。
通常,将式(I)的化合物以合适的制剂形式施用于种子。合适的用于种子处理的制剂和方法对于本领域技术人员是已知的。
可将式(I)的化合物转化为常规的拌种制剂,如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂或其他种子包衣组合物,以及ULV制剂。
这些制剂以已知方式通过将式(I)的化合物与常规添加剂混合而制备,所述常规添加剂为例如常规的增量剂以及溶剂或稀释剂、染料、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、粘着剂、赤霉素以及水。
可存在于可根据本发明使用的拌种制剂中的染料为通常用于此目的的所有染料。可以使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿剂为促进润湿并常用于配制农用化学活性成分的所有物质。可优选使用萘磺酸烷基酯,如萘磺酸二异丙酯或萘磺酸二异丁酯。
可存在于可根据本发明使用的拌种制剂中的合适的分散剂和/或乳化剂为常用于配制农用化学活性成分的所有非离子、阴离子和阳离子分散剂。可优选使用非离子或阴离子分散剂,或非离子或阴离子分散剂的混合物。合适的非离子分散剂尤其包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚,及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其为木素磺酸盐、聚丙烯酸盐和芳基磺酸酯-甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为常用于配制农用化学活性成分的所有抑制泡沫的物质。可优选使用有机硅(silicone)消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为在农用化学组合物中可用于此目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为在农用化学组合物中可用于此目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的粘着剂为可用于拌种产品中的所有常规的粘结剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素(tylose)。
可存在于可根据本发明使用的拌种制剂中的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。赤霉素是已知的(参见R.Wegler“Chemie derPflanzenschutz-und”,第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可用于直接或预先用水稀释后处理各种不同种类的种子。例如,浓缩剂或可通过用水稀释而由其获得的制剂可用于对以下种子进行拌种:谷物(如小麦、大麦、黑麦、燕麦和黑小麦)的种子,以及玉米、稻、油菜、豌豆、菜豆、棉花、向日葵、大豆和甜菜的种子,或各种不同的蔬菜种子。可根据本发明使用的拌种制剂或其稀释的使用形式还可用于对转基因植物的种子进行拌种。
对于用可根据本发明使用的拌种制剂或由其制备的使用形式处理种子而言,所有可常规用于拌种的混合装置都是有用的。具体而言,拌种的过程为:将种子以分批或连续操作的方式置于混合器内;加入特定所需量的拌种制剂(以其本身或在预先用水稀释后);并混合直至制剂均匀地分布在种子上。如果合适,随后进行干燥操作。
可根据本发明使用的拌种制剂的施用率可在相对宽的范围内变化。这由制剂中式(I)的化合物的具体含量和种子决定。式(I)的化合物的施用率通常为每千克种子0.001至50g,优选每千克种子0.01至15g。
动物健康
在动物健康领域,即在兽医学领域,式(I)的化合物对动物寄生虫、特别是体外寄生虫或体内寄生虫具有活性。术语“体内寄生虫”尤其包括蠕虫和原生动物,如球虫(coccidia)。体外寄生虫通常且优选为节肢动物,尤其是昆虫和螨类。
在兽医学领域,具有有利的恒温动物毒性的式(I)的化合物适合于防治在家畜、育种动物、动物园动物、实验室动物、实验动物和家养动物的动物育种和动物饲养中出现的寄生虫。它们对寄生虫的所有或特定的发育阶段具有活性。
农业家畜包括,例如,哺乳动物,如绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿,且特别是牛和猪;家禽,如火鸡、鸭、鹅,且特别是鸡;例如在水产养殖中的鱼和甲壳类动物;以及昆虫,如蜜蜂。
家养动物包括,例如,哺乳动物,如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,以及特别是狗、猫、笼养鸟、爬行动物、两栖动物和观赏鱼。
在一个优选的实施方案中,将式(I)的化合物给予哺乳动物。
在另一个优选的实施方案中,将式(I)的化合物给予鸟类,即笼养鸟,以及特别是家禽。
使用式(I)的化合物来防治动物寄生虫旨在减少或预防疾病、死亡病例和性能下降(在肉、奶、羊毛、皮、蛋、蜜等的情况下),从而使得动物饲养更经济、更简单,并可实现更好的动物健康。
关于动物健康领域,术语“防治”意指式(I)的化合物有效地将特定寄生虫在被这类寄生虫感染的动物中的发病率降低至无害的程度。更具体而言,本文中的“防治”意指式(I)的化合物可杀死各寄生虫、抑制其生长或抑制其繁殖。
节肢动物包括:
虱目(Anoplurida)的节肢动物,例如,血虱属种(Haematopinus spp.)、毛虱属种(Linognathus spp.)、虱属种(Pediculus spp.)、阴虱属种(Phtirus spp.)、管虱属种(Solenopotes spp.);食毛目(Mallophagida)和钝角亚目(Amblycerina)和细角亚目(Ischnocerina)的节肢动物,例如毛羽虱属种(Trimenopon spp.)、禽虱属种(Menoponspp.)、鸭虱属种(Trinoton spp.)、牛羽虱属种(Bovicola spp.)、Werneckiella属种、Lepikentron属种、畜虱属种(Damalina spp.)、啮毛虱属种(Trichodectes spp.)、猫羽虱属种(Felicola spp.);来自双翅目(Diptera)和长角亚目(Nematocerina)和短角亚目(Brachycerina)的节肢动物,例如伊蚊属种(Aedes spp.)、按蚊属种(Anopheles spp.)、库蚊属种(Culex spp.)、蚋属种(Simulium spp.)、真蚋属种(Eusimulium spp.)、白蛉属种(Phlebotomus spp.)、罗蛉属种(Lutzomyia spp.)、库蠓属种(Culicoides spp.)、斑虻属种(Chrysops spp.)、短蚋亚属种(Odagmia spp.)、维蚋属种(Wilhelmia spp.)、瘤虻属种(Hybomitra spp.)、黄虻属种(Atylotus spp.)、虻属种(Tabanus spp.)、麻虻属种(Haematopota spp.)、Philipomyia属种、蜂虱蝇属种(Braula spp.)、蝇属种(Muscaspp.)、齿股蝇属种(Hydrotaea spp.)、螫蝇属种(Stomoxys spp.)、血蝇属种(Haematobiaspp.)、Morellia属种、厕蝇属种(Fannia spp.)、舌蝇属种(Glossina spp.)、丽蝇属种(Calliphora spp.)、绿蝇属种(Lucilia spp.)、金蝇属种(Chrysomyia spp.)、污蝇属种(Wohlfahrtia spp.)、麻蝇属种(Sarcophaga spp.)、Oestrus属种、皮蝇属种(Hypodermaspp.)、胃蝇属种(Gasterophilus spp.)、虱蝇属种(Hippobosca spp.)、Lipoptena属种、蜱蝇属种(Melophagus spp.)、鼻狂蝇属种(Rhinoestrus spp.)、大蚊属种(Tipula spp.);蚤目(Siphonapterida)的节肢动物,例如蚤属种(Pulex spp.)、栉首蚤属种(Ctenocephalides spp.)、潜蚤属种(Tunga spp.)、客蚤属种(Xenopsylla spp.)、角叶蚤属种(Ceratophyllus spp.);
异翅目(Heteropterida)的节肢动物,例如,臭虫属种(Cimex spp.)、锥猎蝽属种(Triatoma spp.)、红猎蝽属种(Rhodnius spp.)、锥蝽属种(Panstrongylus spp.);以及蜚蠊目的令人生厌的害虫和卫生害虫。
节肢动物还包括:
蜱螨亚纲(Acari)(蜱螨目(Acarina))和后气门目(Metastigmata)的节肢动物,例如隐喙蜱科(Argasidae)如锐缘蜱属种(Argas spp.)、钝缘蜱属种(Ornithodorus spp.)、耳疥癣虫属种(Otobius spp.),硬蜱科(Ixodidae)如硬蜱属种(Ixodes spp.)、花蜱属种(Amblyomma spp.)、扇头蜱属种(Rhipicephalus(牛蜱属种(Boophilus))spp.)、革蜱属种(Dermacentor spp.)、Haemophysalis属种、璃眼蜱属种(Hyalomma spp.)、扇头蜱属种(Rhipicephalus spp.)(多宿主蜱虫的原始属种);中气门目(Mesostigmata)的节肢动物如皮刺螨属种(Dermanyssus spp.)、禽刺螨属种(Ornithonyssus spp.)、Pneumonyssus属种、刺利螨属种(Raillietia spp.)、肺刺螨属种(Pneumonyssus spp.)、胸刺螨属种(Sternostoma spp.)、瓦螨属种(Varroa spp.)、蜂盾螨属种(Acarapis spp.);辐螨目(Actinedida)(前气门目(Prostigmata))的节肢动物,例如蜂盾螨属种(Acarapis spp.)、姬螯螨属种(Cheyletiella spp.)、禽螯螨属种(Ornithocheyletia spp.)、肉螨属种(Myobia spp.)、疮螨属种(Psorergates spp.)、蠕形螨属种(Demodex spp.)、恙螨属种(Trombicula spp.)、Neotrombiculla属种、Listrophorus属种;粉螨目(Acaridida)(无气门目(Astigmata))的节肢动物,例如粉螨属种(Acarus spp.)、食酪螨属种(Tyrophagusspp.)、嗜木螨属种(Caloglyphus spp.)、颈下螨属种(Hypodectes spp.)、翅螨属种(Pterolichus spp.)、痒螨属种(Psoroptes spp.)、足螨属种(Chorioptes spp.)、耳螨属种(Otodectes spp.)、疥螨属种(Sarcoptes spp.)、背肛螨属种(Notoedres spp.)、疙螨属种(Knemidocoptes spp.)、胞螨属种(Cytodites spp.)、鸡雏螨属种(Laminosioptesspp.)。
寄生性原生动物包括:
鞭毛纲(Mastigophora(Flagellata)),例如,锥虫科(Trypanosomatidae),例如,布鲁斯锥虫(Trypanosoma b.brucei)、冈比锥虫(T.b.gambiense)、罗德森锥虫(T.b.rhodesiense)、刚果锥虫(T.congolense)、克鲁兹锥虫(T.cruzi)、伊氏锥虫(T.evansi)、马锥虫(T.equinum)、刘氏锥虫(T.lewisi)、鲈鱼锥虫(T.percae)、猿猴锥虫(T.simiae)、活跃锥虫(T.vivax)、巴西利什曼虫(Leishmania brasiliensis)、多氏利什曼虫(L.donovani)、热带利什曼虫(L.tropica),例如毛滴虫科(Trichomonadidae),例如兰氏贾第虫(Giardia lamblia)、犬贾第虫(G.canis);
肉鞭毛虫亚门(Sarcomastigophora)(根足虫纲(Rhizopoda)),例如内阿米巴科(Entamoebidae),例如痢疾内阿米巴(Entamoeba histolytica);哈氏虫科(Hartmanellidae),例如棘变形虫属种(Acanthamoeba sp.)、哈氏虫属种(Harmanellasp.);
顶复亚门(Apicomplexa)(孢子纲(Sporozoa)),例如艾美虫科(Eimeridae),例如堆形艾美虫(Eimeria acervulina)、腺样艾美虫(E.adenoides)、阿州艾美虫(E.alabamensis)、鸭艾美虫(E.anatis)、鹅艾美虫(E.anserina)、阿氏艾美虫(E.arloingi)、阿洛尼氏艾美虫(E.ashata)、奥本艾美虫(E.auburnensis)、牛艾美虫(E.bovis)、波氏艾美虫(E.brunetti)、犬艾美虫(E.canis)、美栗鼠艾美虫(E.chinchillae)、E.clupearum、鸽艾美虫(E.columbae)、E.contorta、槌状艾美虫(E.crandalis)、德氏艾美虫(E.debliecki)、散布艾美虫(E.dispersa)、椭圆艾美虫(E.ellipsoidales)、镰刀形艾美虫(E.falciformis)、福氏艾美虫(E.faurei)、黄色艾美虫(E.flavescens)、加洛帕沃尼艾美虫(E.gallopavonis)、哈氏艾美虫(E.hagani)、肠艾美虫(E.intestinalis)、E.iroquoina、无残艾美虫(E.irresidua)、唇艾美虫(E.labbeana)、勒氏艾美虫(E.leucarti)、大型艾美虫(E.magna)、巨型艾美虫(E.maxima)、中型艾美虫(E.media)、珠鸡艾美虫(E.meleagridis)、火鸡和缓艾美虫(E.meleagrimitis)、和缓艾美虫(E.mitis)、毒害艾美虫(E.necatrix)、雅氏艾美虫(E.ninakohlyakimovae)、羊艾美虫(E.ovis)、小型艾美虫(E.parva)、孔雀艾美虫(E.pavonis)、穿孔艾美虫(E.perforans)、E.phasani、梨形艾美虫(E.piriformis)、早熟艾美虫(E.praecox)、E.residua、粗糙艾美虫(E.scabra)、E.spec.、斯氏艾美虫(E.stiedai)、猪艾美虫(E.suis)、禽艾美虫(E.tenella)、树艾美虫(E.truncata)、特鲁特艾美虫(E.truttae)、邱氏艾美虫(E.zuernii);格洛虫属种(Globidium spec.),贝氏等孢子虫(Isospora belli)、犬等孢子虫(I.canis)、猫等孢子虫(I.felis)、俄亥俄等孢子虫(I.ohioensis)、I.rivolta、等孢子虫属种(I.spec.)、猪等孢子虫(I.suis)、Cystisospora属种、隐抱属种(Cryptosporidium spec.),特别是C.parvum;例如弓形虫科(Toxoplasmadidae),例如鼠弓形虫(Toxoplasma gondii)、Hammondia heydornii、Neospora caninum、贝斯虫(Besnoitia besnoitii);例如肉抱子虫科(Sarcocystidae),例如牛犬肉抱子虫(Sarcocystis bovicanis)、牛人肉抱子虫(S.bovihominis)、羊犬肉孢子虫(S.ovicanis)、羊猫肉孢子虫(S.ovifelis)、S.neurona、肉抱子虫属种(S.spec.)、猪人肉抱子虫(S.suihominis),例如Leucozoidae如Leucozytozoon simondi,例如症原虫科(Plasmodiidae),例如伯氏鼠症原虫(Plasmodium berghei)、镰状症原虫(P.falciparum)、三日症原虫(P.malariae)、卵形症原虫(P.ovale)、间日症原虫(P.vivax),症原虫属种(P.spec.),例如焦虫纲(Piroplasmea),例如阿根廷巴贝虫(Babesia argentina)、牛巴贝虫(B.bovis)、犬巴贝虫(B.canis)、巴贝虫属种(B.spec.)、泰勒原虫(Theileria parva),泰勒虫属种(Theileria spec.),例如匿虫亚目(Adeleina),例如犬肝簇虫(Hepatozooncanis)、肝簇虫属种(H.spec.);
蠕虫的病原性体内寄生虫包括扁形动物门(Platyhelmintha)(例如,单殖亚纲(Monogenea)、绦虫类(cestodes)和吸虫类(trematodes))、线虫类(nematodes)、棘头动物门(Acanthocephala)和舌形动物门(Pentastoma)。它们包括:
单殖亚纲(Monogenea):例如,三代虫属种(Gyrodactylus spp.)、指环虫属种(Dactylogyrus spp.)、多盘吸虫属种(Polystoma spp.);
绦虫类:假叶目(Pseudophyllidea)的绦虫,例如,裂头属种(Diphyllobothriumspp.)、迭宫绦虫属种(Spirometra spp.)、裂头绦虫属种(Schistocephalus spp.)、舌状绦虫属种(Ligula spp.)、吸叶绦虫属种(Bothridium spp.)、大复殖孔绦虫属种(Diplogonoporus spp.);
圆叶目(Cyclophyllida)的绦虫:例如,中殖孔绦虫属种(Mesocestoides spp.)、裸头绦虫属种(Anoplocephala spp.)、副裸头绦虫属种(Paranoplocephala spp.)、蒙尼茨绦虫属种(Moniezia spp.)、繸体绦虫属种(Thysanosoma spp.)、曲子宫绦虫属种(Thysanieziaspp.)、无卵黄腺绦虫属种(Avitellina spp.)、斯泰绦虫属种(Stilesia spp.)、鸣绦虫属种(Cittotaenia spp.)、Andyra属种、伯特绦虫属种(Bertiella spp.)、带绦虫属种(Taenia spp.)、棘球绦虫属种(Echinococcus spp.)、泡尾绦虫属种(Hydatigera spp.)、戴文氏绦虫属种(Davainea spp.)、瑞立绦虫属种(Raillietina spp.)、膜壳绦虫属种(Hymenolepis spp.)、棘鳞绦虫属种(Echinolepis spp.)、Echinocotyle属种、双睾绦虫属种(Diorchis spp.)、复孔绦虫属种(Dipylidium spp.)、约优克斯绦虫属种(Joyeuxiellaspp.)、复孔绦虫属种(Diplopylidium spp.);
吸虫类:复殖纲(Digenea)的吸虫,例如:双穴吸虫属种(Diplostomum spp.)、茎双穴吸虫属种(Posthodiplostomum spp.)、血吸虫属种(Schistosoma spp.)、毛毕吸虫属种(Trichobilharzia spp.)、鸟毕吸虫属种(Ornithobilharzia spp.)、澳毕吸虫属种(Austrobilharzia spp.)、巨毕吸虫属种(Gigantobilharzia spp.)、彩蚴吸虫属种(Leucochloridium spp.)、短咽吸虫属种(Brachylaima spp.)、棘口吸虫属种(Echinostoma spp.)、棘缘吸虫属种(Echinoparyphium spp.)、棘隙吸虫属种(Echinochasmus spp.)、低颈吸虫属种(Hypoderaeum spp.)、片形吸虫属种(Fasciolaspp.)、Fascioloides属种、姜片吸虫属种(Fasciolopsis spp.)、环腔吸虫属种(Cyclocoelum spp.)、盲腔吸虫属种(Typhlocoelum spp.)、同盘吸虫属种(Paramphistomum spp.)、杯殖吸虫属种(Calicophoron spp.)、殖盘吸虫属种(Cotylophoron spp.)、巨孔吸虫属种(Gigantocotyle spp.)、菲策吸虫属种(Fischoederius spp.)、腹袋吸虫属种(Gastrothylacus spp.)、背孔吸虫属种(Notocotylus spp.)、下弯吸虫属种(Catatropis spp.)、斜睾吸虫属种(Plagiorchisspp.)、前殖吸虫属种(Prosthogonimus spp.)、双腔吸虫属种(Dicrocoelium spp.)、阔盘吸虫属种(Eurytrema spp.)、隐孔吸虫属种(Troglotrema spp.)、并殖吸虫属种(Paragonimus spp.)、肛瘤吸虫属种(Collyriclum spp.)、侏形吸虫属种(Nanophyetusspp.)、后睾吸虫属种(Opisthorchis spp.)、支睾吸虫属种(Clonorchis spp.)、次睾吸虫属种(Metorchis spp.)、异形吸虫属种(Heterophyes spp.)、后殖吸虫属种(Metagonimusspp.);
线虫类:毛形线虫科(Trichinellida),例如:鞭虫属种(Trichuris spp.)、毛细线虫属种(Capillaria spp.)、Paracapillaria属种、优鞘属种(Eucoleus spp.)、Trichomosoides属种、毛线虫属种(Trichinella spp.);
垫刃目(Tylenchida)的线虫,例如:细丝鲶属种(Micronema spp.)、类圆线虫属种(Strongyloides spp.);
杆形目(Rhabditida)的线虫,例如:圆线虫属种(Strongylus spp.)、三齿属种(Triodontophorus spp.)、食道齿属种(Oesophagodontus spp.)、毛线属种(Trichonemaspp.)、辐首线虫属种(Gyalocephalus spp.)、柱咽属种(Cylindropharynx spp.)、杯口线虫属种(Poteriostomum spp.)、Cyclococercus属种、杯冠属种(Cylicostephanus spp.)、结节线虫属种(Oesophagostomum spp.)、夏柏特线虫属种(Chabertia spp.)、肾线虫属种(Stephanurus spp.)、钩口线虫属种(Ancylostoma spp.)、钩虫属种(Uncinaria spp.)、板口线虫属种(Necator spp.)、仰口线虫属种(Bunostomum spp.)、球头线虫属种(Globocephalus spp.)、比翼线虫属种(Syngamus spp.)、杯口线虫属种(Cyathostomaspp.)、后圆线虫属种(Metastrongylus spp.)、网尾线虫属种(Dictyocaulus spp.)、缪勒线虫属种(Muellerius spp.)、原圆线虫属种(Protostrongylus spp.)、新圆线虫属种(Neostrongylus spp.)、囊尾线虫属种(Cystocaulus spp.)、肺圆线虫属种(Pneumostrongylus spp.)、Spicocaulus属种、麂圆线虫属种(Elaphostrongylus spp.)、拟马鹿圆线虫属种(Parelaphostrongylus spp.)、环体线虫属种(Crenosoma spp.)、Paracrenosoma属种、奥斯勒丝虫属种(Oslerus spp.)、管圆线虫属种(Angiostrongylusspp.)、猫圆线虫属种(Aelurostrongylus spp.)、类丝虫属种(Filaroides spp.)、副类丝虫属种(Parafilaroides spp.)、毛圆线虫属种(Trichostrongylus spp.)、血矛线虫属种(Haemonchus spp.)、胃线虫属种(Ostertagia spp.)、背带线虫属种(Teladorsagiaspp.)、马歇尔线虫属种(Marshallagia spp.)、古柏线虫属种(Cooperia spp.)、日圆线虫属种(Nippostrongylus spp.)、螺旋线虫属种(Heligmosomoides spp.)、细颈线虫属种(Nematodirus spp.)、猪圆线虫属种(Hyostrongylus spp.)、尖柱线虫属种(Obeliscoidesspp.)、裂口线虫属种(Amidostomum spp.)、沃鲁线虫属种(Ollulanus spp.);
旋尾目(Spirurida)的线虫,例如:尖尾线虫属种(Oxyuris spp.)、蛲虫属种(Enterobius spp.)、栓尾线虫属种(Passalurus spp.)、管状线虫属种(Syphacia spp.)、无刺线虫属种(Aspiculuris spp.)、异刺线虫属种(Heterakis spp.);蛔虫属种(Ascarisspp.)、弓蛔线虫属种(Toxascaris spp.)、弓蛔虫属种(Toxocara spp.)、贝利蛔线虫属种(Baylisascaris spp.)、副蛔虫属种(Parascaris spp.)、异尖线虫属种(Anisakis spp.)、鸡蛔虫属种(Ascaridia spp.);颚口线虫属种(Gnathostoma spp.)、泡翼线虫属种(Physaloptera spp.)、吸吮线虫属种(Thelazia spp.)、筒线虫属种(Gongylonema spp.)、丽线虫属种(Habronema spp.)、副柔线虫属种(Parabronema spp.)、德拉西线虫属种(Draschia spp.)、龙线虫属种(Dracunculus spp.);冠丝虫属种(Stephanofilariaspp.)、副丝虫属种(Parafilaria spp.)、腹腔丝虫属种(Setaria spp.)、罗阿丝虫属种(Loa spp.)、恶丝虫属种(Dirofilaria spp.)、光丝虫属种(Litomosoides spp.)、布鲁线虫属种(Brugia spp.)、吴策线虫属种(Wuchereria spp.)、盘尾丝虫属种(Onchocercaspp.)、旋尾线虫属种(Spirocerca spp.);
棘头动物门:少棘目(Oligacanthorhynchida),例如:巨吻棘头虫属种(Macracanthorhynchus spp.)、前睾棘头虫属种(Prosthenorchis spp.);多形目(Polymorphida),例如:细颈棘头虫属种(Filicollis spp.);念珠目(Moniliformida),例如:念珠棘虫属种(Moniliformis spp.);
棘吻目(Echinorhynchida),例如棘头虫属种(Acanthocephalus spp.)、棘吻虫属种(Echinorhynchus spp.)、似细吻棘头虫属种(Leptorhynchoides spp.);
舌形动物门:蛇舌状虫目(Porocephalida),例如舌形虫属种(Linguatula spp.)。
在兽医领域和动物饲养中,通过本领域通常已知的方法(如经肠内、肠外、真皮或鼻途径)以合适制剂的形式给予式(I)的化合物。给予可为预防性或治疗性的。
因此,本发明的一个实施方案涉及式(I)的化合物作为药物的用途。
另一个方面涉及式(I)的化合物作为抗体内寄生虫剂(antiendoparasiticagent)、特别是杀蠕虫剂(helminthicidal agent)或抗原生动物剂(antiprotozoicagent)的用途。式(I)的化合物适合于例如在动物育种、动物饲养、动物笼舍和卫生领域中用作抗体内寄生虫剂、尤其是杀蠕虫剂或抗原生动物剂。
另一个方面还涉及式(I)的化合物作为抗体外寄生虫剂(antiectoparasiticagent)、特别是杀节肢动物剂如杀昆虫剂或杀螨剂的用途。另一个方面涉及式(I)的化合物例如在动物饲养、动物育种、动物笼舍或卫生领域中用作抗体外寄生虫剂、特别是杀节肢动物剂如杀昆虫剂或杀螨剂的用途。
抗蠕虫混合组分
例如可提及以下抗蠕虫混合组分:
抗蠕虫活性化合物,包括杀吸虫和杀绦虫活性化合物:
大环内酯类,例如:阿维菌素(abamectin)、多拉菌素(doramectin)、依马菌素(emamectin)、依立诺克丁(eprinomectin)、伊维菌素(ivermectin)、美倍霉素(milbemycin)、莫西菌素(moxidectin)、奈马克丁(nemadectin)、塞拉菌素(selamectin);
苯并咪唑(benzimidazole)类和probenzimidazole类,例如:阿苯达唑(albendazole)、阿苯达唑亚砜(albendazole-sulfoxide)、坎苯达唑(cambendazole)、环苯达唑(cyclobendazole)、苯硫氨酯(febantel)、芬苯达唑(fenbendazole)、氟苯达唑(flubendazole)、甲苯达唑(mebendazole)、奈托比胺(netobimin)、奥芬达唑(oxfendazole)、奥苯达唑(oxibendazole)、帕苯达唑(parbendazole)、噻苯达唑(thiabendazole)、托布津(thiophanate)、三氯苯达唑(triclabendazole);
环辛缩酹肽(cyclooctadepsipeptide)类,例如:emodepside、PF1022;
氨基乙腈衍生物类,例如:莫奈太尔(monepantel);
四氢嘧啶类,例如:莫仑太尔(morantel)、噻嘧啶(pyrantel)、奥克太尔(oxantel);
咪唑并噻唑(imidazothiazole)类,例如:丁咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
水杨酰苯胺(salicylanilide)类,例如:溴沙尼特(bromoxanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯生太尔(closantel)、氯硝柳胺(niclosamide)、羟氯扎胺(oxyclozanide)、雷复尼特(rafoxanide)、三溴沙仑(tribromsalan);
paraherquamide类,例如:得曲恩特(derquantel)、paraherquamide;
氨基苯基脒类,例如:阿米太尔(amidantel)、脱酰阿米太尔(dAMD)、三苯双脒(tribendimidine);
有机磷酸酯类,例如:蝇毒磷(coumaphos)、育畜磷(crufomate)、敌敌畏(dichlorvos)、哈洛克酮(haloxon)、naphthalofos、敌百虫(trichlorfon);
取代的酚类,例如:硫氯酚(bithionol)、二碘硝酚(disophenol)、六氯酚(hexachlorophene)、硝氯酚(niclofolan)、meniclopholan、硝碘酚腈(nitroxynil);
哌嗪酮(piperazinone)类,例如:吡喹酮(praziquantel)、依西太尔(epsiprantel);
各种其他种类,例如:硝硫氰胺(amoscanate)、酚乙铵(bephenium)、丁萘脒(bunamidine)、氯硝安定(clonazepam)、氯舒隆(clorsulon)、地芬尼泰(diamfenetid)、双氯酚(dichlorophen)、乙胺嗪(diethylcarbamazine)、依米丁(emetine)、三氯苯哌嗪(hetolin)、海恩酮(hycanthone)、硫蒽酮(lucanthone)、盐酸卢甘宋(Miracil)、mirasan、氯硝柳胺(niclosamide)、尼立达唑(niridazole)、硝碘酚腈(nitroxynile)、硝硫氰酯(nitroscanate)、奥替普拉(oltipraz)、omphalotin、奥沙尼喹(oxamniquin)、巴龙霉素(paromomycin)、哌嗪(piperazine)、雷琐太尔(resorantel)。
病媒防治(vector
control)
式(I)的化合物还可用于病媒防治。在本发明的上下文中,病媒是能将病原体例如病毒、蠕虫、单细胞生物和细菌从贮主(reservoir)(植物、动物、人类等)传播到宿主的节肢动物,尤其是昆虫或蛛形纲动物。病原体可被机械地传播至宿主(例如通过非叮咬蝇(non-stinging fly)传播沙眼)或可在注射后传播至宿主(例如通过蚊子传播疟原虫)。
病媒及其传播的疾病或病原体的实例为:
1)蚊
-按蚊:疟疾、丝虫病;
-库蚊:日本脑炎、丝虫病、其他病毒性疾病、蠕虫的传播;
-伊蚊:黄热病、登革热、丝虫病、其他病毒性疾病;
-蚋科:蠕虫的传播,特别是旋盘尾丝虫(Onchocerca volvulus);
2)虱:皮肤感染、流行性斑疹伤寒;
3)蚤:鼠疫、地方性斑疹伤寒;
4)蝇:昏睡病(锥虫病);霍乱、其他细菌性疾病;
5)螨:螨病、流行性斑疹伤寒、立克次氏体痘、土拉菌病、圣路易斯型脑炎、蜱媒脑炎(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、疏螺旋体病(borreliosis);
6)蜱:borellioses如达氏疏螺旋体(Borrelia duttoni)、蜱媒脑炎、Q热(贝氏柯克斯体(Coxiella burnetii))、巴贝西虫病(babesioses)(犬巴贝虫(Babesia canis canis))。
在本发明的上下文中,病媒的实例为可将植物病毒传播至植物的昆虫,例如蚜虫、蝇、叶蝉或蓟马。能传播植物病毒的其他病媒为叶螨、虱、甲虫和线虫。
在本发明的上下文中,病媒的其他实例为可将病原体传播至动物和/或人的昆虫和蛛形纲动物,如蚊,尤其是伊蚊属,按蚊属,例如冈比亚按蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、不吉按蚊(A.funestus)、大劣按蚊(A.dirus)(疟疾),和库蚊属;虱;蚤;蝇;螨和蜱。
如果式(I)的化合物为破坏抗性(resistance-breaking)的,则病媒防治也是可行的。
式(I)的化合物适用于预防通过病媒传播的疾病和/或病原体。因此,本发明的另一个方面为式(I)的化合物用于例如在农业、园艺、林业、花园和休闲设施中,以及在材料和贮存产品的保护中的病媒防治的用途。
工业材料保护
式(I)的化合物适用于保护工业材料免受昆虫的侵袭或破坏,所述昆虫例如来自鞘翅目(Coleoptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鳞翅目(Lepidoptera)、啮虫目(Psocoptera)和衣鱼目(Zygentoma)。
在本文中,工业材料应理解为意指无生命材料,如优选塑料、粘合剂、胶料、纸类和卡片、皮革、木材、加工的木制品和涂料组合物。特别优选本发明用于保护木材的用途。
在另一个实施方案中,式(I)的化合物与至少一种其他杀昆虫剂和/或至少一种杀真菌剂一起使用。
在另一个实施方案中,式(I)的化合物以即用型农药的形式存在,即它可以不经进一步的修饰而应用于所述材料。特别地,合适的其他杀昆虫剂或杀真菌剂为上文提及的那些。
出乎意料地,还已发现,式(I)的化合物可用于保护与盐水或微咸水接触的物体(特别是船体、筛、网、建筑物、系泊用具和信号系统)免受污损。式(I)的化合物也可以单独地或与其他活性成分结合用作防污剂。
卫生领域中的动物害虫的防治
式(I)的化合物适用于防治卫生领域中的动物害虫。更具体而言,本发明可用于家用保护领域、卫生保护领域和贮存产品的保护中,特别是用于防治在封闭空间(例如住所、工厂车间、办公室、车辆舱室)中遇到的昆虫、蛛形纲动物和螨。为了防治动物害虫,将式(I)的化合物单独使用或与其他活性成分和/或助剂结合使用。它们优选用于家用杀昆虫剂产品中。式(I)的化合物对敏感和抗性物种以及对所有发育阶段均有效。
这些害虫包括例如以下害虫:蛛形纲(Arachnida),蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足纲(Chilopoda)和倍足纲(Diplopoda);昆虫纲(Insecta),蜚蠊目(Blattodea)、鞘翅目(Coleoptera)、革翅目(Dermaptera)、双翅目(Diptera)、异翅目(Heteroptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鳞翅目(Lepidoptera)、虱目(Phthiraptera)、啮虫目(Psocoptera)、跳跃目(Saltatoria)或直翅目(Orthoptera)、蚤目(Siphonaptera)和衣鱼目(Zygentoma);以及软甲亚纲(Malacostraca),等足目(Isopoda)。
以下列形式进行施用:例如,气雾剂、无压喷雾产品(如泵式喷雾剂和雾化喷雾剂)、自动起雾体系、喷雾剂、泡沫剂、凝胶剂、具有由纤维素或塑料制成的蒸发片剂(evaporator tablet)的蒸发产品、液体蒸发剂、凝胶和薄膜蒸发剂、推进器驱动的蒸发剂、无动力或无源的蒸发体系、捕蛾纸、捕蛾袋和捕蛾胶,作为颗粒剂或粉剂,用于撒播的饵料中或饵站(bait station)中。
本发明的另一个方面为式(I)的化合物作为除草剂的用途。
制备方法
本发明的化合物可通过本领域技术人员已知的常规方法进行制备。
反应方案1示出了本发明化合物(Ia)和(Ib)的一般制备方法。
反应方案1
基团A1、A2、A3、Z、T、B1、B2、B3、B4、B5、R1和R2如上文所定义。Alk为C1-C4-烷基。
通过活化中间体2并随后使经活化的中间体与通式3的胺进行反应,可获得本发明通式(Ia)的化合物。对于这种酰胺化步骤,已记载了许多反应条件。可在Houben-Weyl,Methoden der Organischen Chemie,Volume E5(Georg Thieme Verlag Stuttgart),第934页找到综述。这些反应中的一些通过中间体羰基氯化物进行,该中间体羰基氯化物可以分离使用或原位产生。通式3的胺或其盐可以商购获得,或者可以通过本领域技术人员已知的方法制备。
本发明通式(Ia)的化合物的酰胺官能团可以通过合适的硫化试剂(例如Lawesson试剂或硫化磷(V))转化成硫代酰胺官能团,由此形成本发明通式(Ib)的化合物(参见,例如WO 2004/018439)。
通式2的羧酸可由通式1的羧酸酯,根据已知的文献方法,借助于合适的碱(如氢氧化锂或氢氧化钠水溶液)在合适的溶剂或稀释剂(如二氧六环或THF)中进行水解而获得。
在反应方案1a中,示出了通式1c的中间体的一般制备方法。
反应方案1a
基团A1、A2、A3、B1、B2、B3、B4、B5、R1和R2具有上文所述的定义。T为T1、T2或T3。Alk为C1-C4-烷基。如果M为硼酸、硼酸酯或卤化锌,则U为溴或碘。如果M为溴、碘或三氟甲磺酸根,则U为硼酸、硼酸酯或卤化锌。
通式1c的化合物可由反应参与物4和5通过钯催化的反应来制备(参见,例如WO2011/149874;WO 2014/152115;WO 2010/093885;Organic&biomolecular chemistry(2016),14,第2352页)。通式5的化合物可商购获得或可通过本领域技术人员已知的方法制备(参见,例如WO 2009/106441;WO 2012/038743;Angewandte Chemie,InternationalEdition(2013),52,第7818页)。通式4的化合物可通过已知的文献方法制备(参见,例如WO2016/174052;Organic&biomolecular chemistry(2016),14,第2352页)。
在反应方案1b中,示出了通式1d的中间体的一般制备方法。
反应方案1b
基团A1、A2、A3、B1、B2、B3、B4和B5具有上文所述的定义。Alk为C1-C4-烷基。
通式1d的中间体可以由通式8和6的中间体通过类似于已知的文献方法获得。在这里,肟8首先与合适的卤化试剂(如N-卤代琥珀酰亚胺)反应,然后在合适的碱(例如三乙胺)存在下与通式6的乙炔反应(参见,例如European Journal of Medicinal Chemistry2014,82,214-224;WO 2016/174052)。
通式8的肟是已知的或者可以由通式7的醛通过类似于已知的文献方法制备(例如Bioorganic&Medicinal Chemistry 2012,20,5763-5773;J.Chem.Soc.Perk.Trans.11980,4,1029-1037)。通式7的醛可商购获得或可通过本领域技术人员已知的方法制备。通式6的炔是已知的或可以通过类似于已知的文献方法制备(参见,例如WO 2016/174052)。
在反应方案1c中,示出了通式1e的中间体的一般制备方法。
反应方案1c
基团A1、A2、A3、B1、B2、B3、B4和B5具有上文所述的定义。Alk为C1-C4-烷基。M为氟、氯、溴或碘。
通式1e的中间体可通过通式10的叠氮化物与通式6的乙炔的Cu-催化(参见,例如WO 2008/074835)反应来获得。
通式10的叠氮化物可由通式9的胺通过类似于已知的文献方法来获得(例如Tetrahedron Lett.2013,54,1294-1297;Tetrahedron 2009,65,2678-2683)。通式9的胺可商购获得或可通过本领域技术人员已知的方法制备。
或者,通式10的叠氮化物可由通式5的卤化物(其中M为氟、氯、溴或碘)通过亲核取代来获得。与叠氮化钠的反应通过热活化(参见,例如WO 2010/121675或WO 2012/107434)或在Cu催化(参见,例如WO 2014/114532)下进行。在Cu催化下的反应可在通式6的炔的存在下进行,使得用于获得通式1c的中间体的反应以一锅法进行(参见,例如BeilsteinJ.Org.Chem.2012,8,683–692)。
在反应方案1d中,示出了通式1f的中间体的一般制备方法。
反应方案1d
基团A1、A2、A3、B1、B2、B3、B4和B5具有上文所述的定义。Alk为C1-C4-烷基。Alk‘为任选取代的C1-C6-烷基。M为溴或碘。
通式1f的中间体可通过通式11的叠氮化物与通式13的乙炔的Cu-催化反应获得(参见,例如Journal of Combinatorial Chemistry2009,11,947;Journal of MedicinalChemistry 2012,55,5642)。
通式11的叠氮化物是已知的或可通过类似于已知的文献方法来制备(参见,例如WO2016/008830)。通式13的炔是已知的或可以两阶段顺序通过通式5的卤化物与通式12的三烷基甲硅烷基乙炔的过渡金属催化反应,然后剪切甲硅烷基团来获得(参见,例如WO2016/055947)。
在反应方案1e中,示出了通式1g–1i的中间体的制备方法。
反应方案1e
基团B1、B2、B3、B4、B5、R4和T具有上文所述的定义。Alk为C1-C4-烷基。基团A1、A2和A3为N或CR3。
通式1g-1i的中间体可通过合适的碱使通式14-16的中间体去质子化并随后与烷基化剂反应而获得。所用的烷基化剂为,例如,烷基卤化物并结合作为碱的碱金属氢化物或碱金属碳酸盐(参见,例如关于碘甲烷和氢化钠的组合的WO 2015/011281,关于碳酸钾和溴乙烷的组合的WO 2012/038904)。通式14–16的中间体可通过反应方案1a–d中所示的制备方法获得。为此,可使用尤其是通式5、8、10或13的化合物,其中取代基A1、A2或A3之一为N-(叔丁氧基羰基),[参见,例如EP 2594555]。为获得通式14–16的化合物,必须剪切(叔丁氧基羰基)基团,任选地还在酸性条件下(参见,例如WO 2013/092512)。
在反应方案2中,示出了通式1j、1k的中间体和落在通式(Ia)下的本发明化合物的制备方法。
反应方案2
基团B1、B2、B3、B4、B5和T具有上文所述的定义。A3和A2为S、O或N-R4。Hal为氯或溴。V为C1-C4-烷氧基或NR1R2。
通式1j和1k的化合物可以通过使通式17或18的中间体分别与卤化试剂反应而获得。使用的卤化试剂为例如N-卤代琥珀酰亚胺(参见,例如关于Hal=氯的WO 2009/112845、WO2008/098105、关于Hal=溴的WO 2012/137181,WO 2013/079223)。根据反应方案1,其中V为C1-C4-烷氧基的通式1j和1k的化合物可以转化为落在通式(I'a)下的本发明化合物。如果V为NR1R2,则通式1j至1k的化合物为本发明结构(Ia)的化合物。
反应方案3
基团A1、A2、A3、B1、B2、B3、B4、B5、R1和R2具有上文所述的定义。T为T1、T2或T3。Hal为溴或碘。U为硼酸、硼酸酯或卤化锌。
通过活化通式19的羧酸并随后使活化的中间体与通式3的胺反应,可以获得通式20的酰胺。对于该酰胺化步骤,已经记载了许多反应条件。可以在Houben-Weyl,Methodender Organischen Chemie,Volume E5(Georg Thieme Verlag Stuttgart),第934页中找到综述。这些反应中的一些通过中间体羰基氯化物进行,该中间体可以分离或原位产生。通式3的胺或其盐可商购获得或可通过本领域技术人员已知的方法制备。通式19的羧酸可商购或可通过本领域技术人员已知的方法制备(参见,例如关于合成5-溴-2-甲基噻吩-3-甲酸的WO2012/033390)。
通式(Ia)的化合物可通过反应参与物4和20的钯催化的反应来制备(参见,例如关于U=硼酸酯或硼酸的WO2009/112845;关于U=卤化锌的Angewandte ChemieInternational Edition,2013,52,615)。
反应方案4
基团A1、A2、A3、B1、B2、B3、B4、B5、T和R1具有上文所述的定义。R2为C1-C6-烷基。LG为离去基团,如碘或溴。
本发明通式21的化合物根据反应方案4可通过用合适的碱(例如氢化钠)去质子化,并与合适的亲电子试剂(如碘甲烷)反应而转化为本发明通式(Ia)的化合物,其中R2为C1-C6-烷基。
用于制备式(I)的化合物的以下中间体(A)(其中B2和B4在每种情况下为C-H,B1和B5为C-Cl且B3为全氟代的丙基)是由WO2017/025590已知的:
此外,本发明涉及可用于制备式(I)的化合物的以下式(B)和(C)的中间体,其中Z为C,A1为CH,A2为C-CH3,A3为S,Q为O,R2为H,且R1为环烷基或1-氰基环丙基。
试验部分
制备1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-(4,4,5,5-四甲基-1,
3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑
在-39℃下,将2.12mL 1.3m的异丙基氯化镁氯化锂复合物的溶液滴加至1.27g(2.50mmol)1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-碘-1H-吡唑在THF中的溶液中,然后将反应溶液在-38℃下搅拌30分钟。然后滴加0.59mL(2.9mmol)2-异丙氧基-4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷。移除冷却浴并将反应溶液在室温下搅拌1小时。加入饱和的氯化铵溶液并用环己烷反复萃取混合物。将合并的有机相用饱和碳酸氢钠溶液和饱和氯化钠溶液进行洗涤,经硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过MPLC在硅胶上进行色谱纯化(梯度:乙酸乙酯/环己烷0:100→30:70)。得到270mg 1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑。
1H-NMR(400.0MHz,d6-DMSO):
δ=8.3610(1.8);8.0447(2.5);7.9563(1.8);3.3155(30.9);2.5234(1.0);2.5099(19.5);2.5057(38.9);2.5012(51.1);2.4967(37.6);2.4925(18.8);1.3981(3.0);1.2932(16.0);-0.0002(1.8)
制备N-(1-氰基环丙基)-2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-
1H-吡唑-4-基}-1,3-噻唑-4-甲酰胺
阶段1:2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-
1,3-噻唑-4-甲酸甲酯
在100℃下,将1.0g(1.8mmol)1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑、400mg(1.8mmol)2-溴-1,3-噻唑-4-甲酸甲酯、416mg(360μmol)的四(三苯基膦)钯、1.7g(5.2mmol)碳酸铯、8mL1,4-二氧六环和0.8mL水的混合物在微波反应器中加热2小时。将100mL乙酸乙酯加入反应混合物中,用饱和氯化钠水溶液洗涤反应混合物并然后用硫酸钠干燥有机相。过滤掉干燥剂,在减压下除去溶剂。残余物通过制备型薄层色谱法色谱分离(梯度:乙酸乙酯/石油醚)。得到400mg 2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1,3-噻唑-4-甲酸甲酯。
1H-NMR(300.1MHz,d6-DMSO):
δ=8.9335(5.3);8.5257(7.3);8.4429(5.3);8.1134(8.1);6.5446(0.3);3.8618(16.0);3.3211(54.8);2.7275(0.4);2.5074(54.8);2.5017(71.9);2.4960(51.6);2.2712(0.5);0.0109(0.4);-0.0001(10.4);-0.0111(0.4)
阶段2:2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-
1,3-噻唑-4-甲酸
在室温下,将420mg(804μmol)2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1,3-噻唑-4-甲酸甲酯和336mg(800μmol)氢氧化锂一水合物、2mL水和5mL甲醇的混合物搅拌4小时。然后通过加入浓盐酸将溶液调节至pH为5–6并用二氯甲烷萃取混合物。合并的有机相用饱和的氯化钠水溶液洗涤,用硫酸钠干燥并过滤。在减压下除去溶剂。得到510mg的2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1,3-噻唑-4-甲酸与未知杂质的混合物。
1H-NMR(400.2MHz,d6-DMSO):
δ=8.7673(5.0);8.3477(4.3);8.1073(16.0);7.6718(3.4);4.0228(0.6);4.0064(0.5);3.8629(0.5);3.3328(173.3);3.3101(5.0);2.8922(0.4);2.7327(0.3);2.6725(1.3);2.5036(214.5);2.3304(1.3);2.0878(0.3);1.2356(2.2);1.1482(1.3);0.9410(1.4);0.9241(1.4);0.8548(0.4);0.0016(71.0);-0.1479(0.4)
阶段3:N-(1-氰基环丙基)-2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯
基]-1H-吡唑-4-基}-1,3-噻唑-4-甲酰胺
将35mg(0.30mmol)1-氨基环丙腈盐酸盐、114mg(300μmol)N,N,N,N-四甲基-O-(7-氮杂苯并三唑-1-基)脲六氟磷酸盐(HATU)和52mg(0.40mmol)二异丙基乙胺加入100mg来自阶段2的残余物在4mL N,N-二甲基甲酰胺中的溶液中。将反应混合物在室温下搅拌6小时。然后加入饱和氯化钠水溶液并用乙酸乙酯萃取混合物。用饱和氯化钠水溶液洗涤合并的有机相,用硫酸钠干燥并过滤。在减压下除去溶剂。残余物通过HPLC色谱分离。得到19mg的N-(1-氰基环丙基)-2-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1,3-噻唑-4-甲酰胺。
1H-NMR(300.1MHz,d6-DMSO):
δ=9.3332(5.8);8.9075(0.7);8.8701(10.7);8.4267(10.4);8.3503(14.4);8.1109(16.0);6.5159(3.8);5.7424(1.3);3.6057(0.6);3.3890(0.8);3.3134(232.3);3.2896(8.2);2.7270(5.2);2.7211(3.8);2.6517(0.7);2.5849(1.2);2.5065(611.3);2.5007(800.6);2.4951(565.5);2.2766(3.7);2.2704(4.6);2.1633(1.0);2.0899(1.2);2.0495(0.7);1.5985(2.2);1.5789(5.3);1.5703(5.8);1.5529(2.6);1.3563(3.0);1.3396(5.6);1.3301(5.4);1.3117(2.0);1.2342(0.9);0.8563(0.6);0.1949(2.2);0.0108(22.0);-0.0001(542.6);-0.0111(19.3);-0.1987(2.2);-2.2299(0.6);-3.3736(0.6);-3.5153(0.7)
制备4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1-
甲基-1H-吡咯-2-甲酸甲酯
阶段1:4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-
1H-吡咯-2-甲酸甲酯
将1.7g(3.4mmol)1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑、3.0g(9.9mmol)4-溴-1H-吡咯-1,2-二甲酸1-叔丁基2-甲基酯、763mg(660μmol)四(三苯基膦)钯、3.2g(9.8mmol)碳酸铯、20mL1,4-二氧六环和2mL水的混合物在微波反应器中在100℃下加热2小时。将100mL乙酸乙酯加入反应混合物,该反应混合物用饱和氯化钠水溶液洗涤并然后用硫酸钠干燥有机相。过滤掉干燥剂并在减压下除去溶剂。残余物通过制备型薄层色谱法色谱分离(梯度:乙酸乙酯/石油醚)。得到600mg 4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1H-吡咯-2-甲酸甲酯。
1H-NMR(300.1MHz,d6-DMSO):
δ=11.9847(1.1);8.3084(5.9);8.1316(5.9);8.0531(8.7);7.3581(1.8);7.3527(2.2);7.3489(2.2);7.3435(1.8);7.0571(2.0);7.0512(2.8);7.0442(1.8);6.5190(0.4);3.7806(16.0);3.3136(68.4);2.7268(0.5);2.5066(60.6);2.5010(77.6);2.4954(55.0);2.2764(0.4);2.2711(0.5);1.2355(1.5);1.0688(0.8);0.0105(0.5);-0.0001(10.3)
阶段2:4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-
1-甲基-1H-吡咯-2-甲酸甲酯
在0℃下,将58mg(2.4mmol)氢化钠加入600mg(1.19mmol)4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1H-吡咯-2-甲酸甲酯在5mL N,N-二甲基甲酰胺中的溶液中,并将混合物在此温度下搅拌15分钟。然后加入255mg(1.80mmol)碘甲烷。将反应混合物在室温下搅拌6小时,加入冰水并用乙酸乙酯重复萃取混合物。合并的有机相用饱和氯化钠水溶液洗涤,经硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过制备型薄层色谱法色谱分离(梯度:乙酸乙酯/石油醚)。得到400mg 4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1-甲基-1H-吡咯-2-甲酸甲酯。
1H-NMR(300.1MHz,d6-DMSO):
δ=8.2975(5.4);8.0894(5.4);8.0585(8.0);7.4203(2.8);7.4140(2.9);7.1076(3.6);7.1010(3.5);4.1281(0.4);4.1107(1.1);4.0932(1.1);4.0759(0.4);3.8832(14.4);3.7625(16.0);3.7393(0.4);3.3300(7.6);3.1773(4.9);3.1599(5.3);2.5143(7.4);2.5086(14.6);2.5028(19.3);2.4970(13.6);-0.0001(4.1)
制备2-溴-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-
基}噻吩-3-甲酸乙酯
将130mg(730μmol)N-溴代琥珀酰亚胺加入500mg(959μmol)5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酸乙酯在3mL乙酸中的溶液中。将反应混合物在室温下搅拌30分钟,加入饱和盐水溶液并用乙酸乙酯重复萃取混合物。合并的有机相用饱和的氯化钠水溶液洗涤,经硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过柱色谱法在硅胶上色谱分离(梯度:乙酸乙酯/石油醚)。得到390mg2-溴-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酸乙酯。
1H-NMR(300.1MHz,d6-DMSO):
δ=8.6631(8.8);8.6452(0.5);8.3343(8.9);8.0962(13.3);7.5786(11.6);6.5358(1.0);4.3404(2.1);4.3168(6.8);4.2932(7.0);4.2696(2.2);3.3266(121.6);2.7345(0.6);2.7279(0.7);2.5079(93.7);2.5021(122.5);2.4964(85.7);2.2708(0.7);1.3710(0.4);1.3510(7.6);1.3274(16.0);1.3037(7.2);1.2356(0.6);0.0109(0.8);-0.0001(20.1)
制备5-氯-N-环丙基-4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-
吡唑-4-基}-1-甲基-1H-吡咯-2-甲酰胺
在0℃下,将10mg(75μmol)N-氯代琥珀酰亚胺加入45mg(83μmol)N-环丙基-4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1-甲基-1H-吡咯-2-甲酰胺在3mL乙酸中的溶液中。将反应混合物在室温下搅拌30分钟,加入饱和硫代硫酸钠水溶液并将混合物在室温下再搅拌30分钟。然后加入饱和盐水溶液并用乙酸乙酯重复萃取混合物。合并的有机相用饱和氯化钠水溶液洗涤,经硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过HPLC色谱分离。得到13mg 5-氯-N-环丙基-4-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-1-甲基-1H-吡咯-2-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=8.3976(5.6);8.1968(1.5);8.1869(1.5);8.0746(5.5);8.0489(8.4);7.0532(5.8);3.8637(16.0);3.3216(75.3);2.9610(0.3);2.7964(0.5);2.7869(0.8);2.7783(1.1);2.7685(1.2);2.7600(0.8);2.7505(0.5);2.6749(0.5);2.6706(0.7);2.6663(0.5);2.5061(88.6);2.5017(116.5);2.4973(85.5);2.3284(0.7);2.3237(0.5);2.0742(6.1);0.7006(0.7);0.6877(1.9);0.6826(2.7);0.6706(2.5);0.6645(2.2);0.6534(0.9);0.5535(0.9);0.5430(2.8);0.5369(2.5);0.5275(2.2);0.5152(0.7);0.0079(0.7);-0.0002(18.7)
制备2-氯-N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-
吡唑-4-基}噻吩-3-甲酰胺
阶段1:5-溴-N-环丙基噻吩-3-甲酰胺
将一滴N,N-二甲基甲酰胺和1.0mL(11mmol)草酰氯加入1.00g(4.83mmol)5-溴噻吩-3-甲酸在20mL CH2Cl2中的溶液中。将溶液在回流下加热3小时并再次向其中加入1.0mL(11mmol)草酰氯并将混合物在回流下再加热1.5小时。然后在减压下除去溶剂。
在0℃下,将残余物溶于20mL CH2Cl2,加入0.75mL(5.4mmol)三乙胺和0.37mL(5.3mmol)环丙胺并然后将混合物在室温下搅拌过夜。用CH2Cl2稀释反应溶液并用水重复洗涤。有机相用硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过MPLC在RP硅胶上色谱分离(梯度:H2O/乙腈)。得到1.06g 5-溴-N-环丙基噻吩-3-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=8.2864(4.0);8.2781(4.0);8.0736(15.3);8.0696(15.5);7.5558(16.0);7.5517(15.8);3.3238(22.1);2.8055(0.8);2.7956(2.4);2.7861(3.3);2.7774(5.4);2.7676(5.4);2.7590(3.4);2.7495(2.5);2.7395(0.9);2.6718(0.4);2.5250(1.0);2.5116(27.4);2.5072(55.9);2.5028(73.5);2.4983(52.4);2.4940(25.1);2.3339(0.3);2.3294(0.4);2.0756(0.7);0.7038(3.0);0.6915(8.8);0.6859(11.8);0.6739(11.6);0.6679(8.9);0.6566(4.3);0.6354(0.6);0.6174(0.6);0.5848(0.6);0.5747(0.6);0.5452(4.2);0.5347(11.7);0.5280(10.3);0.5245(9.5);0.5185(9.2);0.5065(2.9);-0.0002(3.2)
阶段2:N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡
唑-4-基}噻吩-3-甲酰胺
将380mg(749μmol)1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑、185mg(752μmol)5-溴-N-环丙基噻吩-3-甲酰胺、173mg(150μmol)四(三苯基膦)钯、735mg(2.25mmol)碳酸铯、4mL 1,4-二氧六环和0.4mL水的混合物在微波反应器中在100℃下加热2小时。然后在真空下除去溶剂。将水加入残余物中并用乙酸乙酯萃取混合物。合并的有机相用硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过MPLC在硅胶上色谱分离(梯度:乙酸乙酯/环己烷)。得到262mg N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=8.5643(10.2);8.3084(3.2);8.2986(3.3);8.2151(10.4);8.0821(16.0);7.9803(7.3);7.6416(7.2);3.9294(0.8);3.3239(34.4);2.8354(0.3);2.8251(1.0);2.8159(1.5);2.8070(2.2);2.7975(2.2);2.7888(1.5);2.7794(1.0);2.7690(0.4);2.6719(0.5);2.5066(70.2);2.5027(90.6);2.4990(68.6);2.3299(0.5);1.0695(4.9);0.7210(1.2);0.7080(3.8);0.7032(5.2);0.6910(4.8);0.6853(4.2);0.6742(1.7);0.5698(1.7);0.5593(5.3);0.5528(5.1);0.5438(4.4);0.5313(1.2);0.0000(9.6)
阶段3:2-氯-N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-
1H-吡唑-4-基}噻吩-3-甲酰胺
在10℃下,将13mg(97μmol)N-氯代琥珀酰亚胺在1mL乙酸中的溶液经30分钟加入50mg(86μmol)N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺在2mL乙酸中的溶液中。将反应混合物在60℃下搅拌18小时,加入饱和的硫代硫酸钠水溶液并将混合物在室温下再搅拌30分钟。然后加入饱和的盐水溶液并用乙酸乙酯重复萃取混合物。合并的有机相用硫酸钠干燥,过滤并在减压下除去溶剂。残余物通过HPLC色谱分离(梯度:H2O/乙腈)。得到31mg 2-氯-N-环丙基-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=9.1968(0.4);8.7769(1.0);8.7466(0.4);8.5761(9.3);8.5621(0.6);8.3702(2.5);8.3595(2.6);8.2724(1.1);8.2292(9.3);8.2007(0.6);8.0858(16.0);7.8646(0.6);7.4156(10.1);7.3687(0.6);5.7567(12.1);3.3217(86.6);2.8437(0.4);2.8330(1.0);2.8241(1.4);2.8148(2.0);2.8052(2.0);2.7964(1.3);2.7863(0.9);2.7770(0.4);2.6712(0.9);2.5062(129.2);2.5020(170.7);2.4979(125.2);2.3284(0.9);2.0744(2.6);1.5860(0.4);1.5797(0.4);1.2624(0.4);1.2569(0.4);0.7379(0.5);0.7270(1.4);0.7146(3.3);0.7093(4.5);0.6971(4.3);0.6913(3.6);0.6802(1.5);0.5629(1.5);0.5522(4.5);0.5455(4.3);0.5363(3.9);0.5240(1.4);0.5069(0.5);0.1463(0.3);0.0077(2.5);-0.0002(68.7);-0.1495(0.3)
制备2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)
苯基]-1H-吡唑-4-基}-N-甲基噻吩-3-甲酰胺
阶段1:2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-
基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺
将32mg(0.14mmol)2-氯-1,3-双(甲氧基羰基)胍加入70mg(0.12mmol)N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺在1mL氯仿中的溶液中,并将混合物在室温下搅拌过夜。然后在减压下除去溶剂并将残余物通过HPLC色谱分离(梯度:H2O/乙腈)。得到60mg 2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=9.6859(1.5);9.2607(5.2);8.8019(2.3);8.5964(8.8);8.2949(2.4);8.2366(8.9);8.0890(16.0);7.4870(10.3);3.3210(33.2);2.6752(0.5);2.6709(0.7);2.6665(0.5);2.5240(1.7);2.5104(42.9);2.5062(89.1);2.5018(119.6);2.4974(86.3);2.4932(41.6);2.3289(0.6);2.3237(0.5);1.6520(0.5);1.6379(1.3);1.6310(1.3);1.6175(0.6);1.5987(1.9);1.5843(4.8);1.5774(5.1);1.5644(2.2);1.2817(2.2);1.2682(4.8);1.2615(5.2);1.2469(2.4);1.2329(1.4);1.2262(1.4);1.2118(0.5);0.9264(0.3);0.9097(0.3);0.0077(1.6);-0.0004(42.8);-0.0086(1.6)
阶段2:2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-
基)苯基]-1H-吡唑-4-基}-N-甲基噻吩-3-甲酰胺
在0℃下,将5mg(0.1mmol)氢化钠(55%的矿物油分散体)加入50mg(83μmol)2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}噻吩-3-甲酰胺在四氢呋喃中的溶液中。将悬浮液在0℃下搅拌10分钟,然后加入7μL(0.1mmol)碘甲烷并将混合物在室温下搅拌过夜。用CH2Cl2稀释反应溶液并用水洗涤。用硫酸钠干燥有机相,过滤并在减压下除去溶剂。残余物通过HPLC色谱分离(梯度:H2O/乙腈)。得到25mg 2-氯-N-(1-氰基环丙基)-5-{1-[2,6-二氯-4-(1,1,1,2,3,3,3-七氟丙烷-2-基)苯基]-1H-吡唑-4-基}-N-甲基噻吩-3-甲酰胺。
1H-NMR(400.0MHz,d6-DMSO):
δ=8.8156(1.0);8.6100(9.3);8.3161(1.2);8.2652(8.4);8.0870(16.0);7.3933(12.2);5.7553(1.7);3.3194(128.0);3.0327(13.4);2.9944(2.9);2.6749(1.2);2.6706(1.8);2.6665(1.3);2.5240(4.5);2.5104(109.0);2.5061(227.3);2.5017(304.5);2.4973(220.5);2.4934(108.7);2.3327(1.3);2.3285(1.7);2.3244(1.3);2.0739(0.4);2.0084(0.4);1.9891(0.4);1.7318(0.4);1.7190(0.5);1.7076(0.4);1.6376(2.3);1.4846(0.4);1.4441(2.3);1.4305(4.3);1.4245(4.4);1.4085(1.4);1.2354(3.1);0.8542(0.7);0.1463(0.8);0.0079(5.5);-0.0001(165.6);-0.0084(7.0);-0.1495(0.8)
表I-T1
B2和B4=CH
实施例编号 | B<sub>1</sub> | B<sub>3</sub> | B<sub>5</sub> | R<sub>1</sub> | R<sub>2</sub> | Z | A<sub>1</sub> | A<sub>2</sub> | A<sub>3</sub> | Q |
I-T1-1 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | C-Br | S | O |
I-T1-2 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | C-Br | S | O |
I-T1-3 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | N-CH<sub>3</sub> | C-H | O |
I-T1-4 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | N-CH<sub>3</sub> | C-H | O |
I-T1-5 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | N | C-H | S | O |
I-T1-6 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 苄基 | H | C | C-H | C-Br | S | O |
I-T1-7 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | N | C-Cl | S | O |
I-T1-8 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | N | C-H | S | O |
I-T1-9 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | N-CH<sub>3</sub> | C-Cl | O |
I-T1-10 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | C-CH<sub>3</sub> | S | O |
I-T1-11 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | C-CH<sub>3</sub> | S | O |
I-T1-12 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | C-H | S | O |
I-T1-13 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | C-H | S | O |
I-T1-14 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | C-I | S | O |
I-T1-15 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | C-I | S | O |
I-T1-16 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 环丙基 | H | C | C-H | C-Cl | S | O |
I-T1-17 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | H | C | C-H | C-Cl | S | O |
I-T1-18 | C-Cl | C-i-C<sub>3</sub>F<sub>7</sub> | C-Cl | 1-(氰基)环丙基 | CH<sub>3</sub> | C | C-H | C-Cl | S | O |
所选实施例的NMR数据
NMR峰列表方法
所选实施例的1H NMR数据以1H NMR峰列表的形式说明。对于每个信号峰,首先列出以ppm计的δ值,然后在圆括号内列出信号强度。不同信号峰的一对δ值-信号强度数通过分号彼此间隔列出。
因此,一个实施例的峰列表采取以下形式:
δ1(强度1);δ2(强度2);........;δi(强度i);........;δn(强度n)
尖峰信号的强度与在NMR谱的打印实例中以cm计的信号高度相关,并且示出了信号强度的真实比例。在宽峰信号的情况下,可以示出信号的若干峰或信号的中央,以及其与谱图中的最强信号相比的相对强度。
为了校准1H NMR谱的化学位移,我们使用四甲基硅烷和/或溶剂的化学位移,特别是在DMSO中测量的图谱的情况下。因此,在NMR峰列表中,可以但不一定出现四甲基硅烷峰。
1HNMR峰的列表与常规1H NMR打印件相似,因此通常包含在常规NMR解析中列出的所有峰。
此外,如同常规的1H NMR打印件,它们可以示出溶剂信号、目标化合物的立体异构体(其同样由本发明提供)的信号和/或杂质的峰。
在记录溶剂和/或水的δ范围内的化合物信号时,我们的1H NMR峰的列表示出了标准的溶剂峰,例如在DMSO-d6中DMSO的峰和水的峰,它们通常具有平均较高的强度。
目标化合物的立体异构体的峰和/或杂质的峰通常具有比目标化合物(例如具有>90%的纯度)的峰平均更低的强度。
这样的立体异构体和/或杂质可以是特定的制备方法所特有的。因此,通过参考“副产物指纹”,它们的峰可有助于识别我们的制备方法的再现性。
视需要,通过已知方法(MestreC,ACD模拟,以及使用靠经验估算的预期值)计算目标化合物的峰的专业人员可任选地使用其他强度滤波器来分离目标化合物的峰。这种分离与在常规1HNMR解析中挑选相关峰相似。
1H NMR峰列表的其他细节可在研究公开数据库(Research DisclosureDatabase)第564025号中找到。
生物实施例
猫栉头蚤(Ctenocephalides felis)-与成年猫蚤的体外接触试验
为了涂覆试管,首先将9mg活性成分溶解于1mL分析纯丙酮中,然后用分析纯丙酮稀释到所需浓度。通过在定轨振动器上旋转和振动(在30rpm下振动旋转2h),将250μL溶液均匀分布在25mL玻璃管的内壁和底部上。使用900ppm的活性成分溶液和44.7cm2的内表面积,假设均匀分布,则获得基于面积计5μg/cm2的剂量。
在溶剂蒸发后,在管中放入5至10只成年猫蚤(猫栉头蚤),用带孔的塑料盖密封,并在室温和环境湿度下水平放置培育。48h后,测定功效。为此,将管直立并将蚤敲落到管的底部。将在底部保持静止或以不协调的方式活动的蚤视为死亡或将要死亡。
在该试验中,如果在5μg/cm2的施用率下获得至少80%的功效,则物质显示出良好的抵抗猫栉头蚤的功效。100%的功效意指所有蚤均死亡或将要死亡。0%的功效意指没有蚤受到伤害。
在该试验中,例如,以下制备实施例的化合物在5μg/cm2(=500g/ha)的施用率下显示出100%的功效:1、11、12
血红扇头蜱(Rhipicephalus sanguineus)-与成年棕色犬蜱的体外接触试验
为了涂覆试管,首先将9mg活性成分溶解于1mL分析纯丙酮中,然后用分析纯丙酮稀释到所需浓度。通过在定轨振动器上旋转和振动(在30rpm下振动旋转2h),将250μL溶液均匀分布在25mL玻璃管的内壁和底部上。使用900ppm的活性成分溶液和44.7cm2的内表面积,假设均匀分布,则获得基于面积计5μg/cm2的剂量。
在溶剂蒸发后,在管中放入5至10只成年犬蜱(血红扇头蜱),用带孔的塑料盖密封,并在室温和环境湿度下在黑暗中水平放置培育。48h后,测定功效。为此,将蜱敲落到管的底部,并在45-50℃的热板上培育不超过5min。将在底部保持静止或以不协调的方式活动——即其不能通过向上爬而有意地避开热——的蜱视为死亡或将要死亡。
在该试验中,如果在5μg/cm2的施用率下获得至少80%的功效,则物质显示出良好的抵抗血红扇头蜱的活性。100%的功效意指所有蜱均死亡或将要死亡。0%的功效意指没有蜱受到伤害。
在该试验中,例如,以下制备实施例的化合物在5μg/cm2(=500g/ha)的施用率下显示出100%的功效:1、2、3、11、12、14
在该试验中,例如,以下制备实施例的化合物在5μg/cm2(=500g/ha)的施用率下显示出80%的功效:15
微小牛蜱(Boophilus microplus)-浸渍试验
试验动物:牛蜱(微小牛蜱)Parkhurst品系,SP-抗性
溶剂:二甲基亚砜
将10mg活性成分溶解于0.5mL二甲基亚砜中。为了制备合适的制剂,在每种情况下,将活性成分溶液用水稀释到所需浓度。
将该活性成分制剂用移液管吸移到管中。将8至10只饱食的成年雌牛蜱(微小牛蜱)转移到另一个带洞的管中。将该管浸泡在活性成分制剂中,并使所有蜱完全浸润。在液体耗尽后,将蜱在滤盘上转移到塑料培养皿中,并储存在温控室中。
7天后,通过受精卵的产卵数来评估功效。将目测没有能育性的卵储存在温控箱中,直到约42天后孵化出幼虫。100%的功效意指没有蜱产下任何受精卵;0%的功效意指所有卵都是能育的。
在该试验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出100%的功效:1、2、11、14
微小牛蜱-注射试验
溶剂:二甲基亚砜
为了制备合适的活性化合物制剂,将10mg活性化合物与0.5mL溶剂混合,并用溶剂将浓液稀释到所需浓度。
将1μL活性成分溶液注射到5只饱食的成年雌牛蜱(微小牛蜱)的腹部。将动物转移到培养皿中,并放在温控室中。
7天后,通过受精卵的产卵数来评估功效。将目测没有能育性的卵储存在温控箱中,直到约42天后孵出幼虫。100%的功效意指没有蜱产生任何受精卵;0%的功效意指所有卵都是能育的。
在该试验中,例如,以下制备实施例的化合物在20μg/动物的施用率下显示出100%的功效:1、2、3、4、6、7、10、11、13、14、15
猫栉头蚤-口服试验
溶剂:二甲基亚砜
为了制备合适的活性化合物制剂,将10mg活性成分与0.5mL二甲基亚砜混合。用柠檬酸化的牛血稀释,得到所需浓度。
将约20只未进食的成年猫蚤(猫栉头蚤)放置到顶部和底部用纱布密封的容器内。将底部用石蜡膜密封的金属圆筒放置在容器上。圆筒中包含血液/活性成分制剂,其可透过石蜡膜被蚤吸食。
2天后,测定以%计的杀死率。100%意指所有蚤都已被杀死;0%意指没有蚤被杀死。
在该试验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出100%的功效:1、2、3、4、5、6、8、10、11、12、13、14、15
铜绿蝇(Luciliacuprina)试验
溶剂:二甲基亚砜
为了制备合适的活性成分制剂,将10mg活性成分与0.5mL二甲基亚砜混合,并用水将浓液稀释到所需浓度。
将约20只澳大利亚绵羊绿头蝇(Australian sheep blowfly)(铜绿蝇)的L1幼虫转移到含有切碎的马肉和所需浓度的活性化合物制剂的试验容器中。
2天后,测定以%计的杀死率。100%意指所有幼虫都已被杀死;0%意指没有幼虫被杀死。
在该实验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出100%的功效:1、2、3、4、10、11、12、13、14、15
在该实验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出95%的功效:6
在该实验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出80%的功效:5、8
家蝇(Musca
domestica)试验
溶剂:二甲基亚砜
为了制备合适的活性成分制剂,将10mg活性成分与0.5mL二甲基亚砜混合,并用水将浓液稀释到所需浓度。
在含有用糖溶液和所需浓度的活性成分制剂处理的海绵的容器中放入10只成年家蝇。
2天后,测定以%计的杀死率。100%意指所有家蝇都已被杀死;0%意指没有家蝇被杀死。
在该实验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出100%的功效:1、2、10、11、12、13、14、15
在该实验中,例如,以下制备实施例的化合物在100ppm的施用率下显示出90%的功效:5
桃蚜(Myzus persicae)–口服测试
溶剂:100重量份的丙酮
为了制备合适的活性化合物制剂,将1重量份的活性化合物使用指定重量份的溶剂来溶解,并用水补充直至所需的浓度。
将50μL的活性化合物制剂转移至微量滴定板,并用150μL的IPL41昆虫培养基(33%+15%糖)补充至200μL的最终体积。随后,使用石蜡膜密封该板,在第二个微量滴定板内的桃蚜的混合种群能够刺破并穿过该石蜡膜而吸收溶液。
5天后,测定以%计的功效。100%表示所有蚜虫都已被杀死;0%表示没有蚜虫被杀死。
在本测试中,例如,以下制备实施例的化合物在4ppm的施用率下显示出100%的功效:10、12、16
在本测试中,例如,以下制备实施例的化合物在4ppm的施用率下显示出90%的功效:11
桃蚜(Myzus persicae)-喷洒试验
溶剂:78重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的绿桃蚜(green peach aphid)(桃蚜)侵染的大白菜(Chinesecabbage)(大白菜(Brassica pekinensis))的叶盘上喷洒所需浓度的活性化合物制剂。
5天后,测定以%计的功效。100%意指所有蚜虫都已被杀死;0%意指没有蚜虫被杀死。
在该试验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出100%的功效:1、2、16
在该试验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出90%的功效:11
辣根猿叶甲(Phaedon
cochleariae)-喷洒试验
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向大白菜(Chinese cabbage)(大白菜)的叶盘上喷洒所需浓度的活性化合物制剂,并在干燥后,使芥菜甲虫(辣根猿叶甲)的幼虫栖居于叶盘上。
7天后,测定以%计的功效。100%意指所有甲虫幼虫都已被杀死;0%意指没有甲虫幼虫被杀死。
在该试验中,例如,以下制备实施例的化合物在100g/h的施用率下显示出100%的功效:1、2、3、4、5、9、10、11、12、13、14、15、16、17、18
在该试验中,例如,以下制备实施例的化合物在100g/h的施用率下显示出83%的功效:7、8
草地贪夜蛾(Spodoptera frugiperda)-喷洒试验
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向玉米(maize)(玉米(Zea mays))的叶盘上喷洒所需浓度的活性成分制剂,并在干燥后,使夜蛾(草地贪夜蛾)的毛虫栖居于叶盘上。
7天后,测定以%计的功效。100%意指所有毛虫都已被杀死;0%意指没有毛虫被杀死。
在该实验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出100%的功效:1、2、3、6、9、10、11、12、13、14、15、16、17、18
二斑叶螨(Tetranychus urticae)-喷洒试验,OP-抗性
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的温室红叶螨(greenhouse red spider mite)(二斑叶螨)侵染的菜豆(bean)(菜豆(Phaseolus vulgaris))的叶盘上喷洒所需浓度的活性化合物制剂。
6天后,测定以%计的功效。100%意指所有叶螨都已被杀死;0%意指没有叶螨被杀死。
在该试验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出100%的功效:10、11、13、14、15、16、17
在该试验中,例如,以下制备实施例的化合物在20g/ha的施用率下显示出100%的功效:1、10、11、17
在该试验中,例如,以下制备实施例的化合物在20g/ha的施用率下显示出90%的功效:2、13、15、16
按蚊试验(ANPHGB表面处理)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为了制备合适的活性化合物制剂,将活性化合物溶解于溶剂(2mg/mL)中。将活性化合物制剂用移液管吸移到釉面砖上,并且在干燥后,将冈比亚按蚊品系RSPH(homozygotkdr)的成年蚊子置于经处理的砖上。暴露时间为30分钟。
与经处理的表面接触24小时后,测定以%计的死亡率。100%意指所有蚊子都已被杀死;0%意指没有蚊子被杀死。
在该试验中,例如,以下制备实施例的化合物在100mg/m2的施用率下显示出80-100%的功效:1、2、3、8、6、9、10、14、15
按蚊试验(ANPHFU表面处理)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为了制备合适的活性化合物制剂,将活性化合物溶解于溶剂(2mg/mL)中。将活性化合物制剂用移液管吸移到釉面砖上,并且在干燥后,将不吉按蚊(Anopheles funestus)品系FUMOZ-R(Hunt等人,Med Vet Entomol.2005Sep;19(3):271-5)的成年蚊子置于经处理的砖上。暴露时间为30分钟。
与经处理的表面接触24小时后,测定以%计的死亡率。100%意指所有蚊子都已被杀死;0%意指没有蚊子被杀死。
在该试验中,例如,以下制备实施例的化合物在100mg/m2的施用率下显示出80-100%的功效:1、2、9、10、14、15。
伊蚊试验(AEDSAE表面处理)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为了制备合适的活性化合物制剂,将活性化合物溶解于溶剂(2mg/mL)中。将活性化合物制剂用移液管吸移到釉面砖上,并且在干燥后,将埃及伊蚊品系MONHEIM的成年蚊子置于经处理的砖上。暴露时间为30分钟。
与经处理的表面接触24小时后,测定以%计的死亡率。100%意指所有蚊子都已被杀死;0%意指没有蚊子被杀死。
在该试验中,例如,以下制备实施例的化合物在100mg/m2的施用率下显示出80-100%的功效:1、2、9、10、13、14、15。
对比实施例
辣根猿叶甲(Phaedon cochleariae)-喷洒试验(PHAECO)
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向大白菜(Chinese cabbage)(大白菜)的叶盘上喷洒所需浓度的活性化合物制剂,并在干燥后,使芥菜甲虫(辣根猿叶甲)的幼虫栖居于叶盘上。
在所需时间后,测定以%计的功效。100%意指所有甲虫幼虫都已被杀死;0%意指没有甲虫幼虫被杀死。
在该试验中,例如,与现有技术相比,以下制备实施例的化合物显示出更好的功效:参见表II
草地贪夜蛾(Spodoptera frugiperda)-喷洒试验(SPODFR)
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向玉米(maize)(玉米(Zea mays))的叶盘上喷洒所需浓度的活性化合物制剂,并在干燥后,使夜蛾(草地贪夜蛾)的毛虫栖居于叶盘上。
在所需时间后,测定以%计的功效。100%意指所有毛虫都已被杀死;0%意指没有毛虫被杀死。
在该试验中,例如,与现有技术相比,以下制备实施例的化合物显示出更好的功效:参见表II
桃蚜(Myzus persicae)-喷洒试验(MYZUPE)
溶剂:78重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的绿桃蚜(green peach aphid)(绿桃蚜)侵染的大白菜(Chinesecabbage)(大白菜(Brassica pekinensis))的叶盘上喷洒所需浓度的活性化合物制剂。
在所需时间后,测定以%计的功效。100%意指所有蚜虫都已被杀死;0%意指没有蚜虫被杀死。
在该试验中,例如,与现有技术相比,以下制备实施例的化合物显示出更好的功效:参见表II
二斑叶螨(Tetranychusurticae)-喷洒试验;OP-抗性(TETRUR)溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为了制备合适的活性化合物制剂,将1重量份的活性化合物用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充至所需浓度。为了制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的温室红叶螨(greenhouse red spider mite)(二斑叶螨)侵染的菜豆(bean)(菜豆(Phaseolus vulgaris))的叶盘上喷洒所需浓度的活性化合物制剂。
在所需时间后,测定以%计的功效。100%意指所有叶螨都已被杀死;0%意指没有叶螨被杀死。
在该试验中,例如,与现有技术相比,以下制备实施例的化合物显示出更好的功效:参见表II
表II
Claims (17)
1.通式(I)的化合物,以及式(I)的化合物的盐、N-氧化物和互变异构形式:
其中
R1 为H,任选地在每种情况下彼此独立地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰基、C1-C4-羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基、氧代基取代的或亚氨基取代的C1-C6-烷基、C2-C6-烯基、C2-C6-炔基、C3-C7-环烷基、 C1 -C6-烷基羰基、C1-C6-烷氧基羰基、C6-芳基(C1-C3)-烷基、C10-芳基(C1-C3)-烷基、C14-芳基 (C1-C3)-烷基、3-元杂环基、4-元杂环基、5-元杂环基、6-元杂环基、7-元杂环基、8-元杂环 基、9-元杂环基或10-元杂环基(如硫杂环丁烷基,如硫杂环丁烷-3-基、氧化硫杂环丁烷如1-氧化硫杂环丁烷-3-基、或二氧化硫杂环丁烷如1,1-二氧化硫杂环丁烷-3-基)或3-元杂 环基(C1-C3)-烷基、4-元杂环基(C1-C3)-烷基、5-元杂环基(C1-C3)-烷基、6-元杂环基(C1- C3)-烷基、7-元杂环基(C1-C3)-烷基、8-元杂环基(C1-C3)-烷基、9-元杂环基(C1-C3)-烷基或 10-元杂环基(C1-C3)-烷基,
优选任选被卤素或氰基取代的C3-C7-环烷基,或
C6-芳基(C1-C3)-烷基、C10-芳基(C1-C3)-烷基、C14-芳基(C1-C3)-烷基,其中C6-芳基、C10-芳基、C14-芳基可任选地彼此独立地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基和C1-C4-烷基,或
C1-C6-烷基羰基;
更优选任选地被氰基取代的C3-环烷基,或C6-芳基(C1-C3)-烷基;
R2为H或任选地彼此独立地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、巯基、C1-C4-羧基、碳酰胺基、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基或氧代基取代的C1-C6-烷基;
部分
A1、A2和A3各自独立地为N、O、CR3、S或N-R4,优选N、CR3、S或N-R4,其中A1、A2、A3、Z和环的碳原子形成芳族体系;
R3各自独立地为H、Cl、F、I、Br或任选卤代的C1-C4-烷基,优选甲基;
R4各自独立地为H或任选卤代的C1-C4-烷基,优选甲基;
Q为O或S,优选O;
Z为C或N;优选C;
B1和B5各自独立地为N或C-R5,并且
B2、B3和B4各自独立地为C-R5,其中
R5各自独立地为H、卤素、氰基、硝基、SF5,在每种情况下任选地被一个或多个选自以下的取代基取代:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰基、C1-C4-羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4-烷基、C3-C4-环烷基、C2-C4-烯基、C5-C6-环烯基、C2-C4-炔基、N-单-C1-C4-烷基氨基、N,N-二-C1-C4-烷基氨基、N-C1-C4-烷酰基氨基、C1-C4-烷氧基、C2-C4-烯氧基、C2-C4-炔氧基、C3-C4-环烷氧基、C5-C6-环烯氧基、C1-C4-烷氧基羰基、C2-C4-烯氧基羰基、C2-C4-炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4-烷酰基、C2-C4-烯基羰基、C2-C4-炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4-烷基硫烷基、C3-C4-环烷基硫烷基、C1-C4-烷硫基、C2-C4-烯硫基、C5-C6-环烯硫基、C2-C4-炔硫基、C1-C4-烷基次磺酰基和C1-C4-烷基亚磺酰基(其中包括C1-C4-烷基亚磺酰基的两个对映异构体)、C1-C4-烷基磺酰基、N-单-C1-C4-烷基氨基磺酰基、N,N-二-C1-C4-烷基氨基磺酰基、C1-C4-烷基亚膦酰基、C1-C4-烷基膦酰基(其中对于C1-C4-烷基亚膦酰基或C1-C4-烷基膦酰基,包括两个对映异构体)、N-C1-C4-烷基氨基羰基、N,N-二-C1-C4-烷基氨基羰基、N-C1-C4-烷酰基氨基羰基、N-C1-C4-烷酰基-N-C1-C4-烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苄基、苄氧基、苄硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳基氨基、C10-芳基氨基、C14-芳基氨基、苄基氨基、杂环基和三烷基甲硅烷基,具有通过双键连接的取代基,如C1-C4-亚烷基、氧代基取代的或亚氨基取代的C1-C6-烷基、C3-C6-环烷基、C1-C6-烷氧基、N-C1-C6-烷氧基亚氨基-C1-C3-烷基、C1-C6-烷基硫烷基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、N-C1-C6-烷基氨基或N,N-二-C1-C6-烷基氨基;
T为下文所列的5元杂芳族T1-T4和T6之一,其中与
连接的键用#号表示,
2.根据权利要求1所述的化合物,其中R2为H或甲基。
3.根据前述权利要求中任一项所述的化合物,其中T为T1、T2或T4,特别优选T1。
4.根据前述权利要求中任一项所述的化合物,其中R1为苄基、环丙基或1-CN-环丙基。
5.根据前述权利要求中任一项所述的化合物,其中所述化合物为根据式(Ia)、(Ib)、(Ic)、(Id)或(If)至(1k)的式之一的化合物
6.根据前述权利要求中任一项所述的化合物,其中所述化合物为式(I‘a)的化合物
7.根据前述权利要求中任一项所述的化合物,其中所述化合物为式(I‘b)的化合物
8.根据前述权利要求中任一项所述的化合物,其中所述化合物为式(I‘c)的化合物
9.根据前述权利要求中任一项所述的化合物,其中所述化合物为式(I‘d)的化合物
10.根据前述权利要求中任一项所述的化合物,其特征在于,B2和B4在每种情况下为C-H。
11.根据前述权利要求中任一项所述的化合物,其特征在于,B3为CR5且R5为全卤代的C1-C4-烷基。
12.根据权利要求11所述的化合物,其特征在于,R5为全氟代的C1-C4-烷基,优选全氟代的丙基。
13.杀昆虫组合物,其包含至少一种权利要求1至8中任一项所述的式(I)的化合物以及增量剂和/或表面活性物质。
14.一种保护转基因种子或常规种子以及由其生长的植物免受害虫侵袭的方法,其特征在于,用至少一种权利要求1至12中任一项所述的化合物处理所述种子。
15.权利要求1至12中任一项的化合物或权利要求13所述的杀昆虫组合物用于防治害虫的用途。
16.种子,其中将权利要求1至12中任一项所述的化合物作为包衣成分或作为除包衣之外的另一层或另几层施用于所述种子。
17.式(B)和(C)的中间体化合物
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