CN105980366A - 作为害虫防治剂的六元c-n-连接的芳基硫醚衍生物和芳基亚砜衍生物 - Google Patents
作为害虫防治剂的六元c-n-连接的芳基硫醚衍生物和芳基亚砜衍生物 Download PDFInfo
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- CN105980366A CN105980366A CN201480075563.5A CN201480075563A CN105980366A CN 105980366 A CN105980366 A CN 105980366A CN 201480075563 A CN201480075563 A CN 201480075563A CN 105980366 A CN105980366 A CN 105980366A
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- 239000003531 protein hydrolysate Substances 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 239000002423 protozoacide Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 210000003689 pubic bone Anatomy 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- DZVWKNFPXMUIFA-UHFFFAOYSA-N pyflubumide Chemical compound C1=C(CC(C)C)C(C(OC)(C(F)(F)F)C(F)(F)F)=CC=C1N(C(=O)C(C)C)C(=O)C1=C(C)N(C)N=C1C DZVWKNFPXMUIFA-UHFFFAOYSA-N 0.000 description 1
- DWTVBEZBWMDXIY-UHFFFAOYSA-N pyrametostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=C(C)C(C=2C=CC=CC=2)=NN1C DWTVBEZBWMDXIY-UHFFFAOYSA-N 0.000 description 1
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- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
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- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
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- MIOBBYRMXGNORL-UHFFFAOYSA-N pyrifluquinazon Chemical compound C1C2=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C2N(C(=O)C)C(=O)N1NCC1=CC=CN=C1 MIOBBYRMXGNORL-UHFFFAOYSA-N 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
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- IYYIUOWKEMQYNV-UHFFFAOYSA-N sodium;ethoxy-oxido-oxophosphanium Chemical compound [Na+].CCO[P+]([O-])=O IYYIUOWKEMQYNV-UHFFFAOYSA-N 0.000 description 1
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- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
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- 229940095064 tartrate Drugs 0.000 description 1
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- 229960003080 taurine Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- AWYOMXWDGWUJHS-UHFFFAOYSA-N tebupirimfos Chemical compound CCOP(=S)(OC(C)C)OC1=CN=C(C(C)(C)C)N=C1 AWYOMXWDGWUJHS-UHFFFAOYSA-N 0.000 description 1
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- BJNLLBUOHPVGFT-QRZIFLFXSA-N teichomycin Chemical class CCCCCCCCCC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)OC=2C(=CC(=CC=2)[C@@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@H]2C(N[C@H](C3=CC(O)=CC(O[C@@H]4[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)=C3C=3C(O)=CC=C(C=3)[C@@H](NC3=O)C(=O)N2)C(O)=O)=O)Cl)=C(OC=2C(=CC(C[C@H](C(N4)=O)NC(=O)[C@H](N)C=5C=C(O6)C(O)=CC=5)=CC=2)Cl)C=C1[C@H]3NC(=O)[C@@H]4C1=CC6=CC(O)=C1 BJNLLBUOHPVGFT-QRZIFLFXSA-N 0.000 description 1
- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 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
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- 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
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
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- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000003190 viscoelastic substance Substances 0.000 description 1
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- 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Tropical Medicine & Parasitology (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
公开了式(I)的化合物,其适用于防治动物害虫(其中包括节肢动物,特别是昆虫和螨),
Description
本申请涉及新的杂环化合物,涉及其制备方法以及其用于防治动物害虫的用途,所述动物害虫包括节肢动物且尤其是昆虫。
芳基硫醚和芳基亚砜衍生物以及它们的杀虫和杀螨作用已经从例如WO 1999/055668 A1中已知。芳基喹唑啉酮及其杀虫和杀螨作用已经从WO 2010/100189 A1中已知。
作物保护剂——其还包括农药——必须在例如功效、持久性和作用谱以及可能的用途方面满足很多要求。毒性问题以及与其他活性化合物或制剂助剂的相容性问题起一定作用,合成活性化合物所需要的费用问题也起一定作用。此外,会出现抗性。基于所有这些原因,不能认为对新的作物保护组合物的研究已经结束,而是持续需要新的化合物,其特性相对于已知的化合物至少在个别方面有所改进。
本发明的一个目的是提供在多个方面拓宽或改进农药谱的化合物。
该目的以及没有明确述及但可由本文所讨论的内容辨别或推出的其他目的通过式(I)的新的化合物来实现
其中(实施方案1-1)
V代表氧或代表硫或代表取代的氮;
Q代表取代的碳或代表氮;
R3和R6彼此独立地代表
氢、卤素、氰基或硝基;或
代表烷基、烯基、炔基、烷氧基、烷基硫烷基、烷基亚磺酰基、烷基磺酰基、卤代烷基羰基、烷基羰基或烷氧基羰基,其中上述基团可任选地被取代;或者
代表环烷基、环烷基烷基或环烯基,其中所述环可包含至少一个选自硫、氧和氮的杂原子,条件是两个氧原子不能直接彼此相邻,其中上述基团可任选地被取代;或者
代表芳基、杂芳基、芳基烷基或杂芳基烷基,其中上述基团可任选地被取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、氰基、烷基、卤代烷基、氰基烷基、羟基烷基、烷氧基烷基、烷基硫烷基烷基、烷基亚磺酰基烷基、烷基磺酰基烷基、烯基、卤素烯基、氰基烯基、炔基、卤代炔基、氰基炔基、酰基或烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成任选取代的、饱和或不饱和的三至八元环,所述环任选地被一个以上的独立地选自O、S和N的杂原子所间隔,条件是两个氧原子不能直接彼此相邻;或
W代表氢或卤素;
n代表数字0、1或2;
Y代表氢、卤素、(C1-C6)-烷基、三氟甲基、(C2-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基或氨基;或代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C6)-烷基或(C1-C6)-卤代烷基;
X代表氢、卤素、氰基、(C1-C6)-烷基、(C2-C6)-卤代烷基或(C1-C6)-烷氧基。
还已发现新的式(I)的化合物作为农药具有良好的例如抵抗节肢动物且尤其是昆虫、线虫和螨虫的功效,且通常还具有非常良好的与植物、特别是作物植物的相容性,和/或具有有利的毒理学和/或环境相关的特性。
下面阐述在式(I)的化合物中所示基团的优选取代基或范围(实施方案2-1)。
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C3-C6)-环烷基或(C1-C6)-烷氧基;
R3和R6彼此独立地
代表氢、卤素、氰基或硝基;或
代表(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、
(C1-C5)-烷基羰基、(C1-C5)-卤代烷基羰基或(C2-C6)-烷氧基羰基;或者
代表(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C3)-烷基或(C3-C6)-环烯基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表苯基、杂芳基、苯基-(C1-C3)-烷基或杂芳基-(C1-C3)-烷基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-羟基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C3-C4)-烯基、(C3-C4)-卤代烯基、(C2-C4)-氰基烯基、(C3-C4)-炔基、(C3-C4)-卤代炔基、(C3-C4)-氰基炔基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代的、饱和或不饱和的三至八元环,所述环任选地被一个以上的独立地选自O、S和N的杂原子间隔,条件是两个氧原子不能直接彼此相邻;或
W代表氢或卤素;
n代表数字0或1;
Y代表氢、卤素、(C1-C4)-烷基、三氟甲基、(C2-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或氨基;或
代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C4)-烷基或(C2-C4)-卤代烷基;
X代表氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基或(C1-C4)-烷氧基。
在另一个实施方案(实施方案2-2)中,在式(I)的化合物中所示基团的优选取代基或范围如下:
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基或(C1-C6)-烷氧基;
R3和R6彼此独立地
代表氢、卤素、氰基或硝基;或
代表(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C5)-卤代烷基羰基或(C2-C6)-烷氧基羰基;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-羟基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C3-C4)-烯基、(C3-C4)-卤素烯基、(C2-C4)-氰基烯基、(C3-C4)-炔基、(C3-C4)-卤代炔基、(C3-C4)-氰基炔基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
W代表氢或卤素;
n代表数字0或1;
Y代表氢、卤素、(C1-C4)-烷基、三氟甲基、(C2-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或氨基;或
代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C4)-烷基或(C2-C4)-卤代烷基;
X代表氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基或(C1-C4)-烷氧基。
在另一个实施方案(实施方案2-3)中,在式(I)的化合物中给出的基团的优选取代基或范围如下:
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C3-C6)-环烷基或(C1-C6)-烷氧基;
R3和R6彼此独立地
代表(C1-C5)-烷基羰基;或者
代表(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C3)-烷基或(C3-C6)-环烯基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表苯基、杂芳基、苯基-(C1-C3)-烷基或杂芳基-(C1-C3)-烷基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表NR‘R“,
其中R‘和R“连同它们所连接的氮原子一起可形成任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代的、饱和或不饱和的三至八元环,所述环任选地被一个以上的独立地选自O、S和N的杂原子间隔,条件是两个氧原子不能直接彼此相邻;或
W代表氢或卤素;
n代表数字0或1;
Y代表氢、卤素、(C1-C4)-烷基、三氟甲基、(C2-C4)-卤代烷基、(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或氨基;或代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C4)-烷基或(C2-C4)-卤代烷基;
X代表氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基或(C1-C4)-烷氧基。
下面阐述在式(I)的化合物中所示基团的更优选的取代基或范围(实施方案3-1)。
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基;
R3和R6彼此独立地
代表氢或卤素;或
代表(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基;或者
代表(C3-C6)-环烷基或(C3-C6)-环烷基-(C1-C2)-烷基,其中所有上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基取代;或者
代表苯基或苯基-(C1-C3)-烷基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表选自下列的杂芳基:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、吲哚基、异吲哚基和吲唑基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成饱和的四至六元环,所述环任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代,以及任选地被选自O、S和N的杂原子间隔;
W代表氢或氟;
n代表数字0或1;
Y代表氢、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、氨基、甲基氨基或二甲基氨基;
X代表氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基或乙氧基。
在另一个实施方案(实施方案3-2)中,在式(I)的化合物中给出的基团的更优选的取代基或范围如下:
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基;
R3和R6彼此独立地
代表氢或卤素;或
代表(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
W代表氢或氟;
n代表数字0或1;
Y代表氢、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、氨基、甲基氨基或二甲基氨基;
X代表氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基或乙氧基。
在另一个实施方案(实施方案3-3)中,在式(I)的化合物中给出的基团的更优选的取代基或范围如下:
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基;
R3和R6彼此独立地
代表(C3-C6)-环烷基或(C3-C6)-环烷基-(C1-C2)-烷基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基取代;或者
代表苯基或苯基-(C1-C3)-烷基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表选自下列的杂芳基:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、吲哚基、异吲哚基和吲唑基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表NR‘R“,
其中R‘和R“连同它们所连接的氮原子一起可形成饱和的四至六元环,所述环任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代,以及任选地被选自O、S和N的杂原子间隔;或
W代表氢或氟;
n代表数字0或1;
Y代表氢、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、氨基、甲基氨基或二甲基氨基;
X代表氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基或乙氧基。
下面阐述在式(I)的化合物中所示基团的特别优选的取代基或范围(实施方案4-1)。
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基、甲氧基、环丙基或三氟甲基;
R3和R6彼此独立地代表氢、甲基、乙基、三氟甲基、二氟甲基、二氟氯甲基、环丙基或苯基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
在另一个实施方案(实施方案4-2)中,在式(I)的化合物中给出的基团的特别优选的取代基或范围如下:
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基或三氟甲基;
R3和R6彼此独立地代表氢、甲基、乙基、三氟甲基、二氟甲基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
在另一个实施方案(实施方案4-3)中,在式(I)的化合物中给出的基团的特别优选的取代基或范围如下:
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基、甲氧基、环丙基或三氟甲基;
R3和R6彼此独立地代表二氟氯甲基、环丙基或苯基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
在另一个实施方案(实施方案4-4)中,在式(I)的化合物中给出的基团的特别优选的取代基或范围如下:
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基、甲氧基、环丙基或三氟甲基;
R3和R6彼此独立地代表氢、氟、甲基、乙基、异丙基、三氟甲基、五氟乙基、二氟甲基、1,1-二氟乙基、二氟氯甲基、环丙基或苯基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
在另一个实施方案(实施方案4-5)中,在式(I)的化合物中给出的基团的特别优选的取代基或范围如下:
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基、甲氧基、环丙基或三氟甲基;
R3和R6彼此独立地代表氟、异丙基、五氟乙基、1,1-二氟乙基、二氟氯甲基、环丙基或苯基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
下面阐述在式(I)的化合物中所示基团的非常特别优选的取代基或范围(实施方案5-1)。
V代表氧;
Q代表C-R5,其中
R5代表氢;
R3代表三氟甲基;
R6代表氢;
W代表氟;
n代表数字0或1;
Y代表氯或甲基;
X代表氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,Me)、(Cl,Cl)。
在另一个实施方案(实施方案5-2)中,在式(I)的化合物中给出的基团的非常特别优选的取代基或范围如下:
V代表氧;
Q代表C-R5,其中
R5代表氢或甲基;
R3代表氢、甲基、乙基、环丙基、异丙基、二氟甲基、三氟甲基、五氟乙基、1,1-二氟乙基或苯基;
R6代表氢、氟或甲基;
W代表氟;
n代表数字0或1;
Y代表溴、氯或甲基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,H)、(Me,Cl)、(Me,F)、(Me,Me)、(Cl,Cl)、(Cl,F)、(Cl,H)、(Br,F)。
在上述定义中当硫和/或氮存在于环中时,例如在表述如“其中所述环可包含至少一个选自硫、氧(其中氧原子不能直接相邻)和氮的杂原子”或“其中一个或两个环成员可各自被选自硫、氧(其中氧原子不能直接相邻)和氮的杂原子替代”中,除非另有说明,硫还可以以SO或SO2的形式存在;如果氮不为-N=的形式,则其除NH之外还可以为N-烷基(尤其是N-C1-C6-烷基)的形式。
在最宽泛且优选的定义中,除非另有说明,
卤素选自氟、氯、溴和碘,还优选氟、氯和溴,
杂芳基(hetaryl,与杂芳基(heteroaryl)同义,包括作为更大单元的部分,例如杂芳基烷基)选自呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、苯并异呋喃基、苯并噻吩基、苯并异噻吩基、吲哚基、异吲哚基、吲唑基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、苯并咪唑基、2,1,3-苯并噁二唑基、喹啉基、异喹啉基、噌啉基、酞嗪基、喹唑啉基、喹喔啉基、萘啶基、苯并三嗪基、嘌呤基、蝶啶基和吲嗪基(indolizinyl)。
在进一步优选的定义中,除非另有说明,
卤素选自氟、氯、溴和碘,还优选氟、氯和溴,
卤素取代的基团(例如卤代烷基)为单卤代的或多卤代最高至最大可能数目的取代基。在多卤代的情况下,卤素原子可以相同或不同。卤素为氟、氯、溴和碘,尤其是氟、氯和溴。
饱和或不饱和的烃基,例如烷基或烯基,可各自为直链的,或如果可能为支链的,包括与杂原子结合,例如,烷氧基。
任选取代的基团可为单取代的或多取代的,其中在多取代的情况下,取代基可以相同或不同。如果有意使用或任选地有意使用取代基,除非另有说明,则该取代基为卤素、烷基、环烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基,特别是氟、氯、(C1-C3)-烷基、(C3-C6)-环烷基(特别是环丙基)、氰基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基。
上文以通用术语或在优选范围内给出的基团定义或阐明相应地适用于最终产品(包括具有亚结构(I-A)的式(I)的化合物,其将在下文中阐明),以及适用于原料和中间体。这些基团定义可按照需要彼此组合,即,包括各优选范围之间的组合。
根据本发明,优选其中存在上文作为优选给出的定义的组合的式(I)的化合物,并且上文作为优选所述的每个实施方案构成独立的组合,特别是在实施方案2-1或实施方案2-2或实施方案2-3中所述的组合。
根据本发明,更优选其中存在上文作为更优选给出的定义的组合的式(I)的化合物,并且上文作为更优选所述的每个实施方案构成独立的组合,特别是在实施方案3-1或实施方案3-2或实施方案3-3中所述的组合。
根据本发明,特别优选其中存在上文作为特别优选给出的定义的组合的式(I)的化合物,并且上文作为特别优选所述的每个实施方案构成独立的组合,特别是在实施方案4-1或实施方案4-2或实施方案4-3或实施方案4-4或实施方案4-5中所述的组合。
根据本发明,非常特别优选其中存在上文作为非常特别优选给出的定义的组合的式(I)的化合物,并且上文作为非常特别优选所述的每个实施方案构成独立的组合,特别是在实施方案5-1或实施方案5-2中所述的组合。
在另一个优选的实施方案中,本发明涉及其中Q代表C-R5的式(I)的化合物。这得到式(I-A)的化合物
在由结构(I-A)定义的式(I)的化合物中,基团和结构元素R5、R3、R6、W、n、Y和X具有上述含义,特别是如实施方案1-1中所述的含义。
更特别地,X和Y代表以下(Y,X)组合:(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F),特别优选以下(Y,X)组合:(Me,F)、(Me,Me)、(Cl,Cl)。
在由结构(I-A)定义的式(I)的化合物中,优选其中存在上文作为优选给出的定义的组合的那些化合物,并且上文作为优选所述的每个实施方案构成独立的组合,特别是在实施方案2-1或实施方案2-2或实施方案2-3中所述的组合。
在由结构(I-A)定义的式(I)的化合物中,更优选其中存在上文作为更优选给出的定义的组合的那些化合物,并且上文作为更优选所述的每个实施方案构成独立的组合,特别是在实施方案3-1或实施方案3-2或实施方案3-3中所述的组合。
在由结构(I-A)定义的式(I)的化合物中,特别优选其中存在上文作为特别优选给出的定义的组合的那些化合物,并且上文作为特别优选所述的每个实施方案构成独立的组合,特别是在实施方案4-1或实施方案4-2或实施方案4-3或实施方案4-4或实施方案4-5中所述的组合。
在由结构(I-A)定义的式(I)的化合物中,非常特别优选其中存在上文作为非常特别优选给出的定义的组合的那些化合物,并且上文作为非常特别优选所述的每个实施方案构成独立的组合,特别是在实施方案5-1或实施方案5-2中所述的组合。
式(I)的化合物还可以作为盐、特别是酸加成盐和金属盐络合物存在。式(I)的化合物及其酸加成盐和金属盐络合物具有良好的特别是用于防治动物害虫的功效,所述动物害虫包括节肢动物,以及尤其是昆虫和螨虫。
通式(I)的化合物的合适的盐包括常规的无毒盐,即,与适当的碱形成的盐以及与所添加的酸形成的盐。优选与无机碱形成的盐,例如碱金属盐(例如,钠盐、钾盐或铯盐)、碱土金属盐(例如,钙盐或镁盐)、铵盐;与有机碱及与无机胺形成的盐,例如三乙胺、二环己胺、N,N’-二苄基乙二胺、吡啶盐、甲基吡啶盐或乙醇铵盐;与无机酸形成的盐,例如,盐酸盐、氢溴酸盐、硫酸二氢盐、硫酸三氢盐或磷酸盐;与有机羧酸或磺酸形成的盐,例如甲酸盐、乙酸盐、三氟乙酸盐、马来酸盐、酒石酸盐、甲磺酸盐、苯基磺酸盐或对甲苯磺酸盐;与碱性氨基酸形成的盐,例如精氨酸盐、天冬氨酸盐或谷氨酸盐;等等。
根据取代基的性质,式(I)的化合物还可为立体异构体的形式,即,几何异构体和/或光学活性异构体或不同组成的异构体混合物的形式。本发明既提供纯的立体异构体,也提供这些异构体的任意所需的混合物,即使在本文中通常仅讨论式(I)的化合物。
然而,根据本发明,优选使用式(I)的化合物及其盐的光学活性、立体异构体形式。
因此,本发明既涉及用于防治动物害虫的纯的对映异构体和非对映异构体,也涉及其混合物,所述动物害虫包括节肢动物且尤其是昆虫和螨虫。因此,本发明的单个构型涉及存在的R对映异构体或涉及包含大部分R对映异构体的混合物,优选其中R与S对映异构体的比例为至少60:40,且按照增加的优选性,至少为70:30、75:25、80:20、85:15及90:10。因此,本发明的另一种单个构型涉及存在的S对映异构体,或涉及包含大部分S对映异构体的混合物,优选其中S与R对映异构体的比例为至少60:40,且按照增加的优选性,至少为70:30、75:25、80:20、85:15及90:10。
式(I)的化合物可以以不同的多晶型形式存在或作为不同的多晶型形式的混合物存在。纯的多晶型物和多晶型物混合物构成了本发明的部分主题,且可根据本发明使用。
根据本发明,化合物由式(I)以通用术语进行定义,其包括所有可行的旋转异构体及其混合物。
根据本发明,式(I)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。各种制备方法——其同样构成了本发明的部分主题的——在下文中描述。
制备方法
通式(I)的化合物可分为其中n=0(Ia)、n=1(Ib)和n=2(Ic)的化合物,以及可根据下列方案制备,例如根据方法A和B制备,如申请WO 2010/100189中所述。偏离于这些方法,式(I)的化合物还可以通过下文中所示的方法D和E或方法F和G制备,或通过在WO1999/055668中所述的方法制备。
方法A
式(IIIa)的化合物或其互变异构体可以例如根据方法A通过使式(IVa)的苯胺与式(V)的硝基化合物(其中R*代表羟基或卤素(优选Cl和Br))反应来制备。
由羧酸(R*=羟基)或酰卤(R*=卤素)制备酰胺的许多不同的方法是已知的,例如G.Benz的Comprehensive Organic Synthesis,第1版,Pergamon Press,Oxford,1991,第6卷,第381-417页;P.D.Bailey等人的Comprehensive Organic Functional GroupTransformation,第1版,Elsevier Science Ltd.,Oxford,1995,第5卷,第257-308页以及R.C.Larock的Comprehensive Organic Transformations,第2版,Wiley-VCH,New York,Weinheim,1999,第1929-1994页。酰氯可以被分离或按原位产生的进行使用。
任选地在缩合剂的存在下、任选地在酸活化剂的存在下、任选地在酸受体的存在下和任选地在溶剂的存在下进行酰胺化反应。有用的缩合剂为通常可用于这种酰胺化反应的所有缩合剂。可以提及的实例为酰卤形成剂,例如光气、三氯化磷、草酰氯或亚硫酰氯;碳二亚胺,例如N,N'-二环己基碳二亚胺(DCC)和1-(3-二甲基氨基丙基)-3-乙基碳二亚胺(EDCI);或其他常规缩合剂,例如五氧化二磷、多磷酸、N,N'-羰基二咪唑、2-氯吡啶-1-甲基碘化物(Mukaiyama试剂)、2-乙氧基-N-乙氧基羰基-1,2-二氢喹啉(EEDQ)、三苯基膦/四氯化碳、溴代三吡咯烷基鏻六氟磷酸盐(BROP)、O-(1H-苯并三唑-1-基氧基)三(二甲基氨基)鏻六氟磷酸盐(BOP)、N,N,N',N'-双(四亚甲基)氯脲四氟硼酸盐、O-(1H-苯并三唑-1-基)-N,N,N',N'-四甲基脲六氟磷酸盐(HBTU)、O-(1H-苯并三唑-1-基)-N,N,N',N'-双(四亚甲基)脲六氟磷酸盐、O-(1H-苯并三唑-1-基)-N,N,N',N'-四甲基脲四氟硼酸盐(TBTU)、O-(1H-苯并三唑-1-基)-N,N,N',N'-双(四亚甲基)脲四氟硼酸盐、O-(7-氮杂苯并三唑-1-基)-N,N,N',N'-四甲基脲六氟磷酸盐(HATU)和1-羟基苯并三唑。这些试剂可以独立地使用或如果合适,以结合的方式使用。有用的酸受体为所有常规的无机或有机碱,例如三乙胺、二异丙基乙胺、N-甲基吗啉或N,N-二甲基氨基吡啶。根据本发明,方法A任选地在合适的反应助剂(例如N,N-二甲基甲酰胺或N,N-二甲基氨基吡啶)的存在下进行。
此外,还可使用混合的酸酐来制备(IIIa),如公开在例如J.Am.Chem.Soc 1967,5012中。在该方法中,可使用不同的氯甲酸酯,例如氯甲酸异丁酯、氯甲酸异丙酯。同样为了该目的,可使用二乙基乙酰氯、三甲基乙酰氯等。
通式(IIa)的化合物或其互变异构体可以根据文献中已知的方法例如通过还原通式(IIIa)的硝基化合物来制备。用于这种还原的合适的方法特别为金属介导的反应,例如氯化亚锡(II)、铁粉末、锌粉末、Raney镍、在碳上的钯(0)或二氧化铂(如水合物)。例如用氯化亚锡(II)进行的金属介导的还原可以根据Organic Syntheses Coll.第(III)卷,453中所述的方法进行。
方法B
或者,通式(IIa)的化合物可以根据方法B通过酰化反应进行制备,其中使通式(IVa)的苯胺与合适的式(VI)的羧酸衍生物反应,其中R**优选代表烷基。该反应无需活化就可发生,如B.M.Trost和I.Fleming在Comprehensive Organic Synthesis,编辑Pergamon,1991,第6卷中的记载。或者,文献公开了通过形成酰胺铝的活化方法,如T.Ooi和K.Marouka在Science of Synthesis,编辑Georg Thieme,2003,第7卷,225-246中的记载。这些酰胺铝可以由苯胺或它们的盐通过与三甲基铝反应或它们与1,4-重氮基双环[2.2.3]辛烷(DABCO)的空气稳定的加合物来得到,如S.Woodward在Tet.Lett.2006,47,5767-5769中的记载。
R**还可以代表氢,以便方法A中描述的所有合成方法还将适用于式(IIa)的化合物的合成。
各种方法适用于通式(Ia)的硫醚的制备。可以提及的实例为:由式(IIa)的化合物开始通过环闭合;由式(IVa)的苯胺开始根据方法C通过与式(IX)的化合物反应,或由式(VIIa)的卤化物或式(VIIIa)或(VIIIb)的硼酸开始根据方法D或方法E通过金属-催化反应。
环化
对于Q=C-R5,其中R5代表H或烷基,通式(Ia)的硫醚的制备可以根据文献中已知的方法任选地在溶剂和稀释剂的存在下、任选地在催化量或化学计量量或过量的或代替所述溶剂或稀释剂的有机性质的酸(例如对甲苯磺酸)或无机性质的酸(例如盐酸或硫酸)的存在下,通过式(IIa)的开链前体与原酸酯(例如原甲酸三乙酯或原乙酸三乙酯)的环化来进行。或者,通式(Ia)的硫醚可以利用文献中已知的方法通过与DMF-DMA反应,随后与甲酸反应来制备。
对于Q=C-R5,其中R5代表烷基或卤代烷基,通式(Ia)的硫醚的制备也可以根据文献中已知的方法(例如在专利WO 2008/039489中关于R5=CF3的记载),通过与合适的羧酸酐或酰氯反应来进行。
对于Q=N,式(Ia)的化合物可以根据文献中已知的方法通过式(IIa)的化合物的重氮化来制备。例如,在0至5℃下、在有机酸或无机酸的存在下,通常在水、醇或极性惰性溶剂中,将亚硝酸盐源(例如亚硝酸钠或亚硝酸异丁酯)加入到式(IIa)的化合物中。示例性的反应条件可参见例如专利WO 2004/242572或J.Amer.Chem.Soc.Perkin Trans.1,1980,633-638。
方法C
或者,式(Ia)的化合物可以根据方法C由式(IVa)的苯胺通过与式(IX)的化合物或其互变异构的羟基嘧啶酮反应来制备。如Yang等人在Org.Lett.2009,11,6,1421-1424中的记载,羟基嘧啶酮的N-芳基化在温和的反应条件下进行,例如在大多数情况下在室温或在最高达70℃下,在作为溶剂的乙腈中,利用作为碱的DBU通过与伯胺进行HATU-介导的耦合。
方法D
式(Ia)的化合物的另一制备方法通过在金属催化反应条件下式(VIIa)的卤化物与式(IX)的化合物反应来提供。文献公开了许多方法,例如在Chem.Pharm.Bull.1997,45,4,719-721;Tet.Lett.2006,47,7677-7680;或Synlett 2008,9,1335-1340中,其中在高温(例如从120至150℃)下,在碱和任选的配体存在下,所用的金属源为碘化铜。
方法E
同样,已发现通过金属催化反应使式(VIIIa)的硼酸与式(IX)的化合物反应可以用来制备式(Ia)的化合物。这种反应的综述可参见Synthesis 2011,6,829-856。合适的金属源为乙酸铜(II),如在Synlett 2010,5,721-724;Tetrahedron 2006,62,8,1764-1771;Tetrahedron Lett.2005,46,34,5699-5702或WO 2010/104818中。
根据文献中已知的方法,例如用高碘酸钠使式(VIIIa)的硼酸或其硼酸酯氧化生成式(VIIIb)的亚砜,在金属催化的反应条件下,同样可使(VIIIb)的亚砜与式(IX)的化合物反应生成目标化合物(Ib)。
根据本发明当进行方法D和E时,可以任选地使用适用于这些反应的任何市售的微波装置(例如Anton Paar Monowave 300,CEM Discover S,Biotage Initiator 60)。
或者,通式(Ib)的化合物可以通过类似于本文提及的那些方法以不同的顺序进行的方法来制备,例如根据方法A、B或C通过使式(IVa)的苯胺氧化来得到式(IVb)的亚砜以及它们的进一步的转化。
偏离于这些方法,其中Q=C-R5的式(I)的化合物还可根据方法F进行制备。
例如根据Assiut Univ.J.of Chemistry 2006,45-63,式(IVa)的苯胺可以与式(XXII)的嗪酮反应来得到式(Ia)的目标化合物。式(XXII)的嗪酮是已知的或可通过文献中已知的方法来制备,例如在Journal of the Chemical Society 1965,4240-4246中所述。
偏离于这些方法,式(I)的化合物还可根据方法G进行制备。
例如根据WO 2004/056785,式(IVa)的苯胺可以与式(XXX)的β-酮酯反应来得到式(XXXI)的烯醇。用胺化剂(例如氨(ammoniak)或乙酸铵)使式(XXXI)的烯醇胺化生成式(IIa)的开链化合物。由(IIa)制备式(I)的化合物已经在上文中描述。
在微波中的反应
在进行本发明的方法中,可以任选地使用适用于这些反应的任何市售的微波装置(例如Anton Paar Monowave 300,CEM Discover S,Biotage Initiator 60)。
硫化
用于制备本发明的通式(Ia)或(Ib)的化合物(其中V为硫)的另一种通用方法涉及在合适的溶剂(例如吡啶、二甲苯或异丙基苯)中,借助于合适的硫化剂(例如五硫化二磷或Lawesson’s试剂)使相应前体中的羰基转化成硫代羰基基团。这种变型记载于许多出版物中,例如J.Amer.Chem.Soc.1956,1938-1941、Chem.Pharm.Bull.1962,10,647-652、US3007927、DE 2554866或WO 2000026194。
用于将硫醚氧化为亚砜的通用制备方法
通式(Ib)的化合物可以通过文献中已知的方法在合适的溶剂和稀释剂中由通式(Ia)的化合物例如借助于氧化剂来氧化而制备。合适的氧化剂为,例如,稀硝酸、过氧化氢和过氧羧酸,例如间氯过苯甲酸。合适的溶剂为惰性有机溶剂,通常为乙腈以及卤化溶剂例如二氯甲烷、三氯甲烷或二氯乙烷。
大量的不同的方法适用于产生对映体富集(enantiomerically enriched)的亚砜,如A.R.Maguire在ARKIVOC,2011(i),1-110中的记载:例如使用钛或钒作为最常用的催化剂源,以Ti(OiPr4)或VO(acac)2的形式,连同手性配体和氧化剂(例如叔丁基氢过氧化物(TBHP)、2-苯基丙烷-2-基氢过氧化物(CHP)或过氧化氢)一起对硫醚进行金属催化的非对称氧化;使用手性氧化剂或手性催化剂进行非金属催化的不对称氧化;亚砜的电化学或生物学的不对称氧化以及动力学拆分,和亲核转移(根据Andersen法)。
对映体还可以由外消旋体获得,例如通过手性HPLC以制备级将其分离而获得。
原料和中间体的说明
式(IV)的苯胺、式(VII)的卤化物和式(VIII)的硼酸是用于制备式(I)的化合物的核心结构单元。
通式(IV)的苯胺可以分为其中n=0的化合物(IVa)和n=1的化合物(IVb)。
式(IVa)的苯胺是文献(例如JP2007/284356)中已知的,或其可通过文献中已知的方法合成。
通式(IVa)的苯胺可以例如在以下方案中进行制备:
其中X、Y和W具有上文中给出的含义,AG代表离去基团且PG代表保护基团。
式(XIV)的苯胺是市售可得的或可通过已知的方法来制备。它们可用合适的保护基团(例如乙酰基)进行保护,以生成式(XIII)的化合物。在酸、酸酐或酰氯的存在下,例如,苯胺(XIV)可转化为相应的酰替苯胺(XIII)。用氯磺酸使所保护的苯胺(XIII)氯磺化生成相应的磺酰氯(XII)。可通过文献中已知的方法(例如盐酸中的铁或碘化物)将磺酰氯(XII)还原成二硫化物(XI)。二硫化物(XI)与式(XV)的卤代烷基亲电试剂(其中AG为离去基团,例如氯、溴、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)反应生成硫醚(X)。所述保护基团可通过文献中已知的合适的方法来除去,以获得(IVa)的苯胺。
替代还原成二硫化物(XI),可用合适的还原剂(例如碘/磷)还原磺酰氯(XII)以生成硫代烷基酯(alkyl thioate)(XVII),然后通过合适的方法(例如与氢氧化钾溶液反应)脱保护,以生成式(XVI)的硫醇。硫醇(XVI)与式(XV)的卤代烷基亲电试剂(其中AG代表离去基团,例如氯、溴、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)反应提供硫醚(IVa)。
同样优选地,或者式(IVa)的硫醚可根据以下方案进行制备:
其中X、Y和W具有上文中给出的含义,AG代表离去基团且PG代表保护基团。
用氯磺酸使式(XXI)的硝基芳族化合物氯磺化以生成相应的磺酰氯(XX)。可通过文献中已知的方法(例如碘化物)将磺酰氯(XX)还原成双(硝基芳基)二硫化物(XIX)。可用通常已知的还原剂(例如氢),任选地借助于非均相催化剂(例如Raney镍、活性碳负载的铂或活性碳负载的钯)将二硫化物(XIX)还原成二硫烷二基双苯胺(XVIII),其中一些与相应的氨基芳基硫醇(XVI)形成了混合物。二硫化物(XVIII)或苯硫酚(XVI)与式(XV)的卤代烷基亲电试剂(其中AG代表离去基团,例如氯、溴、碘、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)反应提供式(IVa)的3-[(2,2,2-三氟乙基)硫烷基]苯胺。
通式(VIIa)的卤化物
其中X、Y和W具有上文中给出的含义以及Hal代表氯、溴或碘,由文献(WO2007/034755、JP2007/081019、JP2007/284385、JP2008/260706、JP2008/308448、JP2009/023910或WO2012/176856)已知,或可通过文献中已知的方法来合成,所述方法可以任选地稍微改进。
用于合成通式(VIIa)的碘化物的合适的原料为具有相同式的溴化物,例如根据文献中已知的方法——如果合适在金属催化下——进行卤素交换反应(参见H.Suzuki,Chem.Let.1985,3,411-412;S.L.Buchwald,J.Amer.Chem.Soc.2002,124(50),14844-14845)。如E.B.Merkushev在Synthesis 1988,12,923-937中所述,同样可以由式(IVa)的苯胺在Sandmeyer反应条件下进行合成。
通式(VIIIa)和(VIIIb)的硼酸
其中X、Y和W具有上文中给出的含义,由文献(例如,WO2007/034755、JP2007/284385、JP2009/023910和WO2012/176856)已知,或可通过文献中已知的方法来合成。
另外,特别关注的是在所述过程和方法中所示的中间体。这些中间体也构成了本发明的部分主题。除了上述中间体外,其他中间体如下所述。
本发明还提供式(IIa)的化合物
其中R3、R6、W、X和Y具有上文中给出的含义。
优选的式(IIa)的化合物为其中存在上文作为优选给出的定义的组合的那些,且上文作为优选描述的每个实施方案构成独立的组合。
更优选的式(IIa)的化合物为其中存在上文作为更优选给出的定义的组合的那些,且上文作为更优选描述的每个实施方案构成独立的组合。
特别优选的式(IIa)的化合物为其中存在上文作为特别优选给出的定义的组合的那些,且上文作为特别优选描述的每个实施方案构成独立的组合。
非常特别优选的式(IIa)的化合物为其中存在上文作为非常特别优选给出的定义的组合的那些,且上文作为非常特别优选描述的每个实施方案构成独立的组合。
式(IIa)的化合物可以不同的互变异构体形式存在。因此,还涵盖这些形式,即使未明确示出。
本发明还提供式(XXXI)的化合物
其中R3、R6、W、X和Y具有上文中给出的含义。
优选的式(XXXI)的化合物为其中存在上文作为优选给出的定义的组合的那些,且上文作为优选描述的每个实施方案构成独立的组合。
更优选的式(XXXI)的化合物为其中存在上文作为更优选给出的定义的组合的那些,且上文作为更优选描述的每个实施方案构成独立的组合。
特别优选的式(XXXI)的化合物为其中存在上文作为特别优选给出的定义的组合的那些,且上文作为特别优选描述的每个实施方案构成独立的组合。
非常特别优选的式(XXXI)的化合物为其中存在上文作为非常特别优选给出的定义的组合的那些,以及上文作为非常特别优选描述的每个实施方案构成独立的组合。
式(XXXI)的化合物可以不同的互变异构体形式存在。因此,还涵盖这些形式,即使未明确示出。
异构体
根据取代基的性质,式(I)的化合物可以为几何异构体和/或光学活性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,对映体、非对映体、阻转异构体或几何异构体。因此,本发明既涵盖纯的立体异构体,也涵盖这些异构体的任何混合物。
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/或它们的栖息地。动物害虫的防治优选在农业和林业以及材料保护中进行。除了这些之外,还优选的是用于人体或动物体的外科或治疗性的治疗方法以及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”通常还包括术语“作物保护剂”。
如果式(I)的化合物具有良好的植物耐受性、有利的温血动物毒性和良好的环境相容性,则其适用于保护植物和植物器官免受生物和非生物胁迫因子,以便提高采收产量,改进采收材料的品质,以及防治在农业、园艺业、畜牧业、水产养殖业、林业、花园以及休闲设施、贮存产品及材料的保护、和卫生领域中遇到的动物害虫,特别是昆虫、蜘形纲动物、蠕虫、线虫及软体动物。它们可优选用作农药。它们对通常敏感和抗性的物种以及对全部或某些发育阶段是有效的。上述害虫包括:
来自节肢动物门(Anthropoda)的害虫,尤其是来自蛛形纲(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)、柑橘瘤瘿螨(Aceria sheldoni)、刺皮瘿螨属种(Aculops spp.)、刺瘿螨属种(Aculusspp.)(例如佛氏刺瘿螨(Aculus fockeui)、苹果刺瘿螨(Aculus schlechtendali))、花蜱属种(Amblyomma spp.)、山楂叶螨(Amphitetranychus viennensis)、锐缘蜱属种(Argasspp.)、牛蜱属种(Boophilus spp.)、短须螨属种(Brevipalpus spp.)(例如紫红短须螨(Brevipalpus phoenicis))、蚜苔螨(Bryobia graminum)、苜蓿苔螨(Bryobiapraetiosa)、刺尾蝎属种(Centruroides spp.)、足螨属种(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(Eutetranychus spp.)(例如班氏真叶螨(Eutetranychus banksi))、瘿螨属种(Eriophyes spp.)(例如梨叶肿瘿螨(Eriophyespyri))、家甜食螨(Glycyphagus domesticus)、红足海镰螯螨(Halotydeus destructor)、半跗线螨属种(Hemitarsonemus spp.)(例如茶半跗线螨(Hemitarsonemus latus)(=侧多食跗线螨(Polyphagotarsonemus latus)))、璃眼蜱属种(Hyalomma spp.)、硬蜱属种(Ixodes spp.)、毒蛛属种(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Oligonychus coniferarum、冬青小爪螨(Oligonychus ilicis)、甘蔗小爪螨(Oligonychusindicus)、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychuspratensis)、樟小爪螨(Oligonychus punicae)、Oligonychus yothersi)、钝缘蜱属种(Ornithodorus spp.)、禽刺螨属种(Ornithonyssus spp.)、全爪螨属种(Panonychusspp.)(例如柑桔全爪螨(Panonychus citri)(=Metatetranychus citri)、苹果全爪螨(Panonychus ulmi)(=Metatetranychus ulmi))、桔芸锈螨(Phyllocoptruta oleivora)、Platytetranychus multidigituli、侧多食跗线螨(Polyphagotarsonemus latus)、痒螨属种(Psoroptes spp.)、扇头蜱属种(Rhipicephalus spp.)、根螨属种(Rhizoglyphusspp.)、疥螨属种(Sarcoptes spp.)、中东金蝎(Scorpio maurus)、狭跗线螨属种(Stenotarsonemus spp.)、稻细螨(Steneotarsonemus spinki)、跗线螨属种(Tarsonemusspp.)(例如乱跗线螨(Tarsonemus confusus)、白跗线螨(Tarsonemus pallidus))、叶螨属种(Tetranychus spp.)(例如加拿大叶螨(Tetranychus canadensis)、朱砂叶螨(Tetranychus cinnabarinus)、土耳其斯坦叶螨(Tetranychus turkestani)、二斑叶螨(Tetranychus urticae))、阿氏真恙螨(Trombicula alfreddugesi)、Vaejovis属种、番茄斜背瘤瘿螨(Vasates lycopersici);
来自唇足纲(Chilopoda)的害虫,例如,地蜈蚣属种(Geophilus spp.)、蚰蜓属种(Scutigera spp.);
来自弹尾目或弹尾纲(Collembola)的害虫,例如,武装棘跳虫(Onychiurusarmatus)、绿圆跳虫(Sminthurus viridis);
来自倍足纲(Diplopoda)的害虫,例如,千足虫(Blaniulus guttulatus);
来自昆虫纲的害虫,例如来自蜚蠊目(Blattodea)的害虫,例如东方蜚蠊(Blattaorientalis)、亚洲蜚蠊(Blattella asahinai)、德国小蠊(Blattella germanica)、马德拉蜚蠊(Leucophaea maderae)、古巴蠊属种(Panchlora spp.)、木蠊属种(Parcoblattaspp.)、大蠊属种(Periplaneta spp.)(例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplaneta australasiae))、棕带蜚蠊(Supella longipalpa);
来自鞘翅目(Coleoptera)的害虫,例如,条纹叶甲(Acalymma vittatum)、菜豆象(Acanthoscelides obtectus)、喙丽金龟属种(Adoretus spp.)、杨树萤叶甲(Agelasticaalni)、叩甲属种(Agriotes spp.)(例如直条叩头虫(Agriotes linneatus)、金针虫(Agriotes mancus))、黑菌虫(Alphitobius diaperinus)、六月金龟子(Amphimallonsolstitialis)、家具窃蠹(Anobium punctatum)、星天牛属种(Anoplophora spp.)、花象属种(Anthonomus spp.)(例如棉铃象甲(Anthonomus grandis))、圆皮蠹属种(Anthrenusspp.)、梨象属种(Apion spp.)、甘蔗金龟属种(Apogonia spp.)、隐翅甲属种(Atomariaspp.)(例如甜菜隐食甲(Atomaria linearis))、毛皮蠹属种(Attagenus spp.)、Bariscaerulescens、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)、龟象属种(Ceuthorhynchus spp.)(例如白菜龟象(Ceutorrhynchus assimilis)、油菜茎象甲(Ceutorrhynchus quadridens)、芜菁象甲(Ceutorrhynchus rapae))、跳甲属种(Chaetocnema spp.)(例如甘薯跳甲(Chaetocnemaconfinis)、Chaetocnema denticulata、玉米跳甲(Chaetocnema ectypa))、Cleonusmendicus、宽胸叩头虫属种(Conoderus spp.)、根颈象属种(Cosmopolites spp.)(例如香蕉黑象(Cosmopolites sordidus))、新西兰草地蛴螬(Costelytra zealandica)、叩甲属种(Ctenicera spp.)、象虫属种(Curculio spp.)(例如美核桃象(Curculio caryae)、Curculio caryatrypes、榛子象甲(Curculio obtusus)、Curculio sayi)、锈赤扁谷盗(Cryptolestes ferrugineus)、长角扁谷盗(Cryptolestes pusillus)、杨干象隐喙属种(Cryptorhynchus lapathi)、芒果果核象甲(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)、北方玉米根叶甲(Diabrotica barberi)、南方十一星瓜叶甲(Diabrotica undecimpunctata howardi)、南方十一星瓜叶甲亚种(Diabrotica undecimpunctata undecimpunctata)、西方玉米根叶甲(Diabroticavirgifera virgifera)、墨西哥玉米根叶甲(Diabrotica virgifera zeae))、蛀野螟属种(Dichocrocis spp.)、水稻铁甲(Dicladispa armigera)、Diloboderus属种、食植瓢虫属种(Epilachna spp.)(例如南瓜瓢虫(Epilachna borealis)、墨西哥豆瓢虫(Epilachnavarivestis))、毛跳甲属种(Epitrix spp.)(例如黄瓜跳甲(Epitrix cucumeris)、茄子跳甲(Epitrix fuscula)、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrixsubcrinita)、块茎跳甲(Epitrix tuberis))、钻孔虫属种(Faustinus spp.)、裸蛛甲(Gibbium psylloides)、阔角谷盗(Gnathocerus cornutus)、菜心野螟(Hellulaundalis)、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(Hypomeces squamosus)、咪小蠹属种(Hypothenemus spp.)(例如咖啡果小蠹(Hypothenemus hampei)、暗咪小蠹(Hypothenemus obscurus)、毛竹小蠹(Hypothenemuspubescens))、甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea)、烟草甲(Lasiodermaserricorne)、长头谷盗(Latheticus oryzae)、波缘薪甲属种(Lathridius spp.)、合爪负泥虫属种(Lema spp.)、马铃薯甲虫(Leptinotarsa decemlineata)、银潜蛾属种(Leucoptera spp.)(例如咖啡潜叶蛾(Leucoptera coffeella))、稻根象(Lissorhoptrusoryzophilus)、筒喙象属种(Lixus spp.)、黄胸寡毛跳甲(Luperomorpha xanthodera)、萤叶甲属种(Luperodes spp.)、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.)(例如欧洲鳃金龟(Melolonthamelolontha))、Migdolus属种、墨天牛属种(Monochamus spp.)、Naupactusxanthographus、隐跗郭公虫属种(Necrobia spp.)、黄蛛甲(Niptus hololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilus surinamensis)、Oryzaphagusoryzae、耳象属种(Otiorrhynchus spp.)(例如苹果耳象(Otiorhynchus cribricollis)、苜蓿象鼻虫(Otiorhynchus ligustici)、草莓根耳象(Otiorhynchus ovatus)、粗糙草莓耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳象(Otiorhynchus sulcatus))、小青花金龟(Oxycetonia jucunda)、辣根猿叶虫(Phaedon cochleariae)、食叶鳃金龟属种(Phyllophaga spp.)、鳃金龟(Phyllophaga helleri)、条跳甲属种(Phyllotreta spp.)(例如辣根条跳甲(Phyllotreta armoraciae)、西方黑跳甲(Phyllotreta pusilla)、Phyllotreta ramosa、黄曲条跳甲(Phyllotreta striolata))、日本弧丽金龟(Popilliajaponica)、象甲属种(Premnotrypes spp.)、大谷蠹(Prostephanus truncatus)、跳甲属种(Psylliodes spp.)(例如Psylliodes affinis、油菜兰跳甲(Psylliodeschrysocephala)、忽布跳甲(Psylliodes punctulata))、蛛甲属种(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizopertha dominica)、谷象属种(Sitophilus spp.)(例如小麦象鼻虫(Sitophilus granarius)、Sitophilus linearis、米象(Sitophilusoryzae)、玉米象(Sitophilus zeamais))、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(Sternechuspaludatus))、宽幅天牛属种(Symphyletes spp.)、纤毛象属种(Tanymecus spp.)(例如玉米象鼻虫(Tanymecus dilaticollis)、印度纤毛象(Tanymecus indicus)、甜菜灰象虫(Tanymecus palliatus))、黄粉虫(Tenebrio molitor)、大谷盗(Tenebrioidesmauretanicus)、拟谷盗属种(Tribolium spp.)(例如美洲黑拟谷盗(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(Zabrus tenebrioides));
来自双翅目(Diptera)的害虫,例如,伊蚊属种(Aedes spp.)(例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、骚扰伊蚊(Aedes vexans))、潜蝇属种(Agromyza spp.)(例如苜蓿斑潜蝇(Agromyza frontella)、美洲黍潜蝇(Agromyza parvicornis))、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(Anophelesgambiae))、瘿蚊属种(Asphondylia spp.)、果实蝇属种(Bactrocera spp.)(例如瓜实蝇(Bactrocera cucurbitae)、东方果实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae))、花园毛蚊(Bibio hortulanus)、琉璃蝇(Calliphoraerythrocephala)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、摇蚊属种(Chironomus spp.)、金蝇属种(Chrysomyia spp.)、斑虻属种(Chrysops spp.)、高额麻虻(Chrysozona pluvialis)、锥蝇属种(Cochliomyia spp.)、康瘿蚊属种(Contariniaspp.)(例如葡萄瘿蚊(Contarinia johnsoni)、甘蓝瘿蚊(Contarinia nasturtii)、梨实康瘿蚊(Contarinia pyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱康瘿蚊(Contarinia sorghicola)、麦黄康癭蚊(Contarinia tritici))、人皮蝇(Cordylobiaanthropophaga)、环足摇蚊(Cricotopus sylvestris)、库蚊属种(Culex spp.)(例如尖音库蚊(Culex pipiens)、致乏库蚊(Culex quinquefasciatus))、库蠓属种(Culicoidesspp.)、脉毛蚊属种(Culiseta spp.)、黄蝇属种(Cuterebra spp.)、橄榄大实蝇(Dacusoleae)、叶瘿蚊属种(Dasyneura spp.)(例如油菜叶瘿蚊(Dasineura brassicae))、地种蝇属种(Delia spp.)(例如葱蝇(Delia antiqua)、麦种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum))、人肤蝇(Dermatobia hominis)、果蝇属种(Drosophila spp.)(例如黑腹果蝇(Drosphilamelanogaster)、斑翅果蝇(Drosophila suzukii))、稻象属种(Echinocnemus spp.)、厕蝇属种(Fannia spp.)、胃蝇属种(Gastrophilus spp.)、舌蝇属种(Glossina spp.)、麻虻属种(Haematopota spp.)、毛眼水蝇属种(Hydrellia spp.)、稻潜叶蝇(Hydrelliagriseola)、黑蝇属种(Hylemya spp.)、虱蝇属种(Hippobosca spp.)、皮蝇属种(Hypodermaspp.)、斑潜蝇属种(Liriomyza spp.)(例如菜斑潜蝇(Liriomyza brassicae)、南美斑潜蝇(Liriomyza huidobrensis)、美洲斑潜蝇(Liriomyza sativae))、绿蝇属种(Luciliaspp.)(例如铜绿蝇(Lucilia cuprina))、罗蛉属种(Lutzomyia spp.)、曼蚊属种(Mansoniaspp.)、家蝇属种(Musca spp.)(例如家蝇(Musca domestica)、舍蝇(Musca domesticavicina))、狂蝇属种(Oestrus spp.)、瑞典麦茎蝇(Oscinella frit)、拟长跑摇蚊属种(Paratanytarsus spp.)、Paralauterborniella subcincta、泉蝇属种(Pegomya spp.)(例如甜菜泉蝇(Pegomya betae)、天仙子泉蝇(Pegomya hyoscyami)、悬钩子泉蝇(Pegomyarubivora))、白蛉属种(Phlebotomus spp.)、草种蝇属种(Phorbia spp.)、伏蝇属种(Phormia spp.)、酪蝇(Piophila casei)、Prodiplosis属种、胡萝卜茎蝇(Psila rosae)、绕实蝇属种(Rhagoletis spp.)(例如东部樱桃实蝇(Rhagoletis cingulata)、核桃绕实蝇(Rhagoletis completa)、黑樱桃实蝇(Rhagoletis fausta)、西部樱桃实蝇(Rhagoletisindifferens)、越桔实蝇(Rhagoletis mendax)、苹果实蝇(Rhagoletis pomonella))、麻蝇属种(Sarcophaga spp.)、蚋属种(Simulium spp.)(例如南方蚋(Simuliummeridionale))、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));
来自半翅目(Hemiptera)的害虫,例如Acizzia acaciaebaileyanae、Acizziadodonaeae、木虱(Acizzia uncatoides)、长头蝗(Acrida turrita)、无网长管蚜属种(Acyrthosipon spp.)(例如豌豆蚜(Acyrthosiphon pisum))、Acrogonia属种、Aeneolamia属种、隆脉木虱属种(Agonoscena spp.)、欧洲甘蓝粉虱(Aleyrodes proletella)、蔗粉穴粉虱(Aleurolobus barodensis)、棉粉虱(Aleurothrixus floccosus)、植莲木风(Allocaridara malayensis)、芒果叶蝉属种(Amrasca spp.)(例如小绿叶蝉(Amrascabigutulla)、小叶蝉(Amrasca devastans))、圆尾蚜(Anuraphis cardui)、肾圆盾蚧属种(Aonidiella spp.)(例如红肾圆盾蚧(Aonidiella aurantii)、黄肾圆盾蚧(Aonidiellacitrina)、苏铁肾盾蚧(Aonidiella inornata))、梨瘤蚜(Aphanostigma piri)、蚜属种(Aphis spp.)(例如绣线菊蚜(Aphis citricola)、黑豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphis glycines)、棉蚜(Aphisgossypii)、常春藤蚜(Aphis hederae)、葡萄藤蚜(Aphis illinoisensis)、Aphismiddletoni、鼠李马铃薯蚜(Aphis nasturtii)、夹竹桃蚜(Aphis nerii)、苹果蚜(Aphispomi)、卷叶蚜(Aphis spiraecola)、Aphis viburniphila)、葡萄叶蜂(Arboridiaapicalis)、Arytainilla属种、小圆盾蚧属种(Aspidiella spp.)、圆盾蚧属种(Aspidiotusspp.)(例如常春藤圆盾蚧(Aspidiotus nerii))、Atanus属种、茄沟无网蚜(Aulacorthumsolani)、烟粉虱(Bemisia tabaci)、澳大利亚木虱(Blastopsylla occidentalis)、Boreioglycaspis melaleucae、李短尾蚜(Brachycaudus helichrysii)、微管姆属种(Brachycolus spp.)、甘蓝蚜(Brevicoryne brassicae)、喀目虱属种(Cacopsylla spp.)(例如梨木虱(Cacopsylla pyricola))、小褐稻虱(Calligypona marginata)、丽黄头大叶蝉(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(Chondracrisrosea)、核桃黑斑蚜(Chromaphis juglandicola)、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)、桔软蜡蚧(Coccuspseudomagnoliarum)、咖啡绿蚧(Coccus viridis))、隐瘤蚜(Cryptomyzus ribis)、Cryptoneossa属种、梳木风属种(Ctenarytaina spp.)、黄翅叶蝶属种(Dalbulus spp.)、柑橘粉虱(Dialeurodes citri)、柑橘木虱(Diaphorina citri)、白背盾蚧属种(Diaspisspp.)、履绵蚧属种(Drosicha spp.)、西圆尾蚜属种(Dysaphis spp.)(例如锈条蚜(Dysaphis apiifolia)、车前草蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphistulipae))、灰粉蚧属种(Dysmicoccus spp.)、小绿叶蝉属种(Empoasca spp.)(例如西部马铃薯叶蝉(Empoasca abrupta)、蚕豆小叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoascamaligna)、茄微叶蝉(Empoasca solana)、Empoasca stevensi)、绵蚜属种(Eriosoma spp.)(例如美洲绵蚜(Eriosoma americanum)、苹果绵蚜(Eriosoma lanigerum)、梨根绵蚜(Eriosoma pyricola))、斑叶蝉属种(Erythroneura spp.)、Eucalyptolyma属种、褐木虱属种(Euphyllura spp.)、殃叶蝉(Euscelis bilobatus)、拂粉阶属种(Ferrisia spp.)、咖啡地粉蚧(Geococcus coffeae)、Glycaspis属种、银合欢木虱(Heteropsylla cubana)、颊木虱(Heteropsylla spinulosa)、假桃病毒叶蝉(Homalodisca coagulata)、梅大尾蚜(Hyalopterus arundinis)、桃大尾蚜(Hyalopterus pruni)、吹绵蚧属种(Icerya spp.)(例如吹绵蚧壳虫(Icerya purchasi))、Idiocerus属种、扁喙叶蝉属种(Idioscopusspp.)、灰飞虱(Laodelphax striatellus)、蜡蚧属种(Lecanium spp.)(例如水土坚蚧(Lecanium corni)(=Parthenolecanium corni))、盾蚧属种(Lepidosaphes spp.)(例如榆蛎盾蚧(Lepidosaphes ulmi))、萝卜蚜(Lipaphis erysimi)、斑衣蜡蝉(Lycormadelicatula)、长管蚜属种(Macrosiphum spp.)(例如马铃薯长管蚜(Macrosiphumeuphorbiae)、百合长管蚜(Macrosiphum lilii)、蔷薇长管蚜(Macrosiphum rosae))、二点叶蜂(Macrosteles facifrons)、沫蝶属种(Mahanarva spp.)、高粱蚜(Melanaphissacchari)、Metcalfiella属种、Metcalfa pruinosa、麦无网蚜(Metopolophiumdirhodum)、黑缘平翅斑蚜(Monellia costalis)、Monelliopsis pecanis、瘤蚜属种(Myzusspp.)(例如冬葱瘤蚜(Myzus ascalonicus)、梅瘤蚜(Myzus cerasi)、女贞瘤蚜(Myzusligustri)、堇菜瘤蚜(Myzus ornatus)、桃蚜(Myzus persicae)、烟蚜(Myzusnicotianae))、莴苣衲长管蚜(Nasonovia ribisnigri)、黑尾叶蝉属种(Nephotettixspp.)(例如黑尾叶蝉(Nephotettix cincticeps)、二条黑尾叶蝉(Nephotettixnigropictus))、褐飞虱(Nilaparvata lugens)、Oncometopia属种、Orthezia praelonga、中华稻蝗(Oxya chinensis)、Pachypsylla属种、杨梅粉虱(Parabemisia myricae)、虱啮属种(Paratrioza spp.)(例如马铃薯木虱(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)、绵粉蚧属种(Phenacoccus spp.)(例如美地绵粉蚧(Phenacoccus madeirensis))、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、葡萄根瘤蚜属种(Phylloxeraspp.)(例如Phylloxera devastatrix、警根瘤蚜(Phylloxera notabilis))、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、臀纹粉蚧属种(Planococcus spp.)(例如橘臀纹粉蚧(Planococcus citri))、Prosopidopsylla flava、梨形原绵腊蚧(Protopulvinariapyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属种(Pseudococcus spp.)(例如柑栖粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、拟长尾粉蚧(Pseudococcus longispinus)、葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni))、Psyllopsis属种、木虱属种(Psylla spp.)(例如黄杨木虱(Psylla buxi)、苹木虱(Psylla mali)、梨木虱(Psylla pyri))、金小蜂属种(Pteromalusspp.)、Pyrilla属种、笠圆盾蚧属种(Quadraspidiotus spp.)(例如胡桃园盾蚧(Quadraspidiotus juglansregiae)、杨笠圆盾蚧(Quadraspidiotus ostreaeformis)、梨笠盾蚧(Quadraspidiotus perniciosus))、Quesada gigas、平刺粉蚧属种(Rastrococcusspp.)、缢管蚜属种(Rhopalosiphum spp.)(例如玉米蚜(Rhopalosiphum maidis)、苹草缢管蚜(Rhopalosiphum oxyacanthae)、稻麦蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphum rufiabdominale))、黑盔蚧属种(Saissetia spp.)(例如咖啡黑盔蚧(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、黑蜡蚧(Saissetiaoleae))、葡萄带叶蝉(Scaphoideus titanus)、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidus articulatus)、麦长管蚜(Sitobion avenae)、长唇基飞虱属种(Sogata spp.)、白背飞虱(Sogatella furcifera)、稻飞风属种(Sogatodes spp.)、Stictocephala festina、树粉虱(Siphoninus phillyreae)、Tenalaphara malayensis、Tetragonocephela属种、长斑蚜属种(Tinocallis caryaefoliae)、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))、温室粉虱(Trialeurodes vaporariorum)、尖翅木虱属种(Trioza spp.)(例如柿木虱(Trioza diospyri))、小叶蝉属种(Typhlocyba spp.)、尖盾蚧属种(Unaspis spp.)、葡萄根瘤蚜(Viteus vitifolii)、么叶蝉属种(Zygin spp.);
来自异翅亚目(Heteroptera)的害虫,例如,南瓜缘蝽(Anasa tristis)、拟丽蝽属种(Antestiopsis spp.)、Boisea属种、土长蝽属种(Blissus spp.)、俊盲蝽属种(Calocoris spp.)、微刺盲蝽属(Campylomma livida)、异背长蝽属种(Cavelerius spp.)、臭虫属种(Cimex spp.)(例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimex lectularius)、蝠臭虫(Cimex pilosellus))、白辧麦寄蝇属种(Collaria spp.)、Creontiades dilutus、胡椒缘蝽(Dasynus piperis)、Dichelops furcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属种(Dysdercus spp.)、美洲蝽属种(Euschistus spp.)(例如英雄美洲蝽(Euschistus heros)、褐臭蝽(Euschistus servus)、三色美洲蝽(Euschistus tristigmus)、广斑臭蝽(Euschistus variolarius))、扁盾蝽属种(Eurygaster spp.)、茶翅蝽(Halyomorpha halys)、角盲蝽属种(Heliopeltis spp.)、Horcias nobilellus、稻缘蝽属种(Leptocorisa spp.)、稻缘蝽象(Leptocorisavaricornis)、西部喙缘蝽(Leptoglossus occidentalis)、叶缘缘蝽(Leptoglossusphyllopus)、丽盲蝽属种(Lygocoris spp.)(例如原丽盲蝽(Lygocoris pabulinus))、草盲蝽属种(Lygus spp.)(例如Lygus elisus、豆荚草盲蝽(Lygus hesperus)、美国牧草盲蝽(Lygus lineolaris))、巨股长蝽属种(Macropes excavatus)、黑摩盲蝽(Monalonionatratum)、绿蝽属种(Nezara spp.)(例如稻绿蝽(Nezara viridula))、稻蝽属种(Oebalusspp.)、方背皮蝽(Piesma quadrata)、璧蝽属种(Piezodorus spp.)(例如盖德拟壁蝽(Piezodorus guildinii))、盲蝽属种(Psallus spp.)、Pseudacysta persea、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))、叶蚁属种(Atta spp.)、松叶蜂属种(Diprion spp.)(例如类欧松叶蜂(Diprion similis))、实叶蜂属种(Hoplocampaspp.)(例如Hoplocampa cookei、苹叶蜂(Hoplocampa testudinea))、毛蚁属种(Lasiusspp.)、小家蚁(Monomorium pharaonis)、树蜂虫属种(Sirex spp.)、红火蚁(Solenopsisinvicta)、臭蚁属种(Tapinoma spp.)、树蜂属种(Urocerus spp.)、胡蜂属种(Vespa spp.)(例如黄边胡蜂(Vespa crabro))、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(Oniscus asellus)、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.)、稻麦小白蚁(Microtermesobesi)、土白蚁属种(Odontotermes spp.)、散白蚁属种(Reticulitermes spp.)(例如黄肢散白蚁(Reticulitermes flavipes)、美国散白蚁(Reticulitermes hesperus));
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(Agrotis segetum)、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(Amyelois transitella)、条麦蛾属种(Anarsia spp.)、干煞夜蛾属种(Anticarsia spp.)(例如大豆夜蛾(Anticarsiagemmatalis))、条小卷蛾属种(Argyroploce spp.)、甘蓝夜蛾(Barathra brassicae)、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(Caloptiliatheivora)、烟卷蛾(Capua reticulana)、苹果小卷蛾(Carpocapsa pomonella)、桃蛀果蛾(Carposina niponensis)、冬尺蛾(Cheimatobia brumata)、禾草螟属种(Chilo spp.)(例如Chilo plejadellus、二化螟(Chilo suppressalis))、色卷蛾属种(Choristoneuraspp.)、葡萄果蠹蛾(Clysia ambiguella)、Cnaphalocerus属种、稻纵卷叶野螟(Cnaphalocrocis medinalis)、云卷蛾属种(Cnephasia spp.)、茶枝尖细蛾属种(Conopomorpha spp.)、象甲属种(Conotrachelus spp.)、Copitarsia属种、小卷蛾属种(Cydia spp.)(例如豆荚小卷蛾(Cydia nigricana)、苹果蠹蛾(Cydia pomonella))、Dalaca noctuides、绢野螟属种(Diaphania spp.)、小蔗杆草螟(Diatraea saccharalis)、钻夜蛾属种(Earias spp.)、Ecdytolopha aurantium、南美玉米苗斑螟(Elasmopalpuslignosellus)、甘薯杆螟(Eldana saccharina)、粉斑螟属种(Ephestia spp.)(例如烟草粉斑螟(Ephestia elutella)、地中海斑螟(Ephestia kuehniella))、叶小卷蛾属种(Epinotia spp.)、苹淡褐卷蛾(Epiphyas postvittana)、荚斑螟属种(Etiella spp.)、棕卷蛾属种(Eulia spp.)、女贞细卷蛾(Eupoecilia ambiguella)、毒蛾属种(Euproctisspp.)(例如黄毒蛾(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(Grapholitha spp.)(例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholita prunivora))、甘蔗螟属种(Hedylepta spp.)、铃夜蛾属种(Helicoverpaspp.)(例如棉铃虫(Helicoverpa armigera)、玉米夜蛾(Helicoverpa zea))、实夜蛾属种(Heliothis spp.)(例如烟芽夜蛾(Heliothis virescens))、褐织蛾(Hofmannophilapseudospretella)、同斑螟属种(Homoeosoma spp.)、长卷蛾属种(Homona spp.)、苹果巢蛾(Hyponomeuta padella)、柿举枝蛾(Kakivoria flavofasciata)、贪夜蛾属种(Laphygmaspp.)、茄白翅野螟(Leucinodes orbonalis)、纹潜蛾属种(Leucoptera spp.)(例如咖啡潜叶蛾(Leucoptera coffeella))、潜叶细蛾属种(Lithocolletis spp.)(例如苹果斑幕潜叶蛾(Lithocolletis blancardella))、绿果冬夜蛾(Lithophane antennata)、花翅小蛾属种(Lobesia spp.)(例如葡萄花翅小卷蛾(Lobesia botrana))、豆白隆切根虫(Loxagrotisalbicosta)、毒蛾属种(Lymantria spp.)(例如舞毒蛾(Lymantria dispar))、潜蛾属种(Lyonetia spp.)(例如桃潜叶蛾(Lyonetia clerkella))、黄褐天幕毛虫(Malacosomaneustria)、豆荚野螟(Maruca testulalis)、甘蓝夜蛾(Mamstra brassicae)、稻暮眼蝶(Melanitis leda)、毛胫夜蛾属种(Mocis spp.)、Monopis obviella、粘虫(Mythimnaseparata)、橡长角蛾(Nemapogon cloacellus)、水螟属种(Nymphula spp.)、Oiketicus属种、麦茎夜蛾属种(Oria spp.)、瘤丛螟属种(Orthaga spp.)、茎野螟属种(Ostrinia spp.)(例如欧洲玉米螟(Ostrinia nubilalis))、黑角负泥虫(Oulema melanopus)、水稻负泥虫(Oulema oryzae)、小眼夜蛾(Panolis flammea)、稻弄蝶属种(Parnara spp.)、红铃虫属种(Pectinophora spp.)(例如棉红铃虫(Pectinophora gossypiella))、潜跳甲属种(Perileucoptera spp.)、茄麦蛾属种(Phthorimaea spp.)(例如马铃薯麦蛾(Phthorimaeaoperculella))、桔潜蛾(Phyllocnistis citrella)、小潜细蛾属种(Phyllonorycterspp.)(例如金纹小潜细蛾(Phyllonorycter blancardella)、山楂潜叶蛾(Phyllonoryctercrataegella))、粉蝶属种(Pieris spp.)(例如菜粉蝶(Pieris rapae))、荷兰石竹小卷蛾(Platynota stultana)、印度谷斑螟(Plodia interpunctella)、金翅夜蛾属种(Plusiaspp.)、菜蛾(Plutella xylostella)(=钻石背蛾(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)、Rachiplusia nu、禾螟属种(Schoenobius spp.)(例如三化螟(Schoenobius bipunctifer))、白禾螟属种(Scirpophaga spp.)(例如稻白螟属种(Scirpophaga innotata))、黄地老虎(Scotiasegetum)、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)、草地夜蛾(Spodoptera frugiperda)、Spodopterapraefica)、展足蛾属种(Stathmopoda spp.)、花生麦蛾(Stomopteryx subsecivella)、透翅蛾属种(Synanthedon spp.)、安第斯马铃薯块茎蛾(Tecia solanivora)、大豆夜蛾(Thermesia gemmatalis)、木塞谷蛾(Tinea cloacella)、袋谷蛾(Tinea pellionella)、幕谷蛾(Tineola bisselliella)、卷蛾属种(Tortrix spp.)、毛毡衣蛾(Trichophagatapetzella)、粉夜蛾属种(Trichoplusia spp.)(例如粉纹夜蛾(Trichoplusia ni))、三化螟(Tryporyza incertulas)、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,家蟋蟀(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.)(例如飞蝗(Locusta migratoria))、黑蝗属种(Melanoplus spp.)(例如Melanoplusdevastator)、乌苏里拟寰螽(Paratlanticus ussuriensis)、沙漠蝗(Schistocercagregaria);
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(Phylloxera vastatrix)、阴虱(Ptirus pubis)、啮毛虱属种(Trichodectes spp.);
来自啮虫目(Psocoptera)的害虫,例如,Lepinatus属种、粉啮虫属种(Liposcelisspp.);
来自蚤目(Siphonaptera)的害虫,例如,角叶蚤属种(Ceratophyllus spp.)、栉首蚤属种(Ctenocephalides spp.)(例如犬栉头蚤(Ctenocephalides canis),猫栉头蚤(Ctenocephalides felis))、跳蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤(Xenopsylla cheopis);
来自缨翅目(Thysanoptera)的害虫,例如,玉米黄呆蓟马(Anaphothripsobscurus)、稻蓟马(Baliothrips biformis)、葡萄镰蓟马(Drepanothris reuteri)、Enneothrips flavens、花蓟马属种(Frankliniella spp.)(例如烟褐蓟马(Frankliniellafusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniellaschultzei)、麦花蓟马(Frankliniella tritici)、越桔花蓟马(Frankliniellavaccinii)、威廉期花蓟马(Frankliniella williamsi))、阳蓟马属种(Heliothripsspp.)、温室条篱蓟马(Hercinothrips femoralis)、葡萄蓟马(Rhipiphorothripscruentatus)、硬蓟马属种(Scirtothrips spp.)、小豆蘧带蓟马(Taeniothripscardamoni)、蓟马属种(Thrips spp.)(例如棕榈蓟马(Thrips palmi)、烟蓟马(Thripstabaci));
来自衣鱼目(Zygentoma)(=缨尾亚目(Thysanura))的害虫,例如,栉衣鱼属种(Ctenolepisma spp.)、蠹鱼(Lepisma saccharina)、衣鱼(Lepismodes inquilinus)、家衣鱼(Thermobia domestica);
来自综合纲(Symphyla)的害虫,例如,幺蚰属种(Scutigerella spp.)(例如无斑点幺蚰(Scutigerella immaculata));
来自软体动物门(Mollusca)的害虫,例如来自双壳纲(Bivalvia)的害虫,如饰贝属种(Dreissena spp.),
以及来自腹足纲(Gastropoda)的害虫,例如阿勇蛞蝓属种(Arion spp.)(例如黑红阿勇蛞蝓(Arion ater rufus))、双脐螺属种(Biomphalaria spp.)、小泡螺属种(Bulinus spp.)、野蛞蝓属种(Deroceras spp.)(例如田灰蛞蝓(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(Plathelminthes)和线虫动物门(Nematoda)的动物和人体寄生虫,例如猫圆线虫属种(Aelurostrongylus spp.)、裂口线虫属种(Amidostomum spp.)、钩口线虫属种(Ancylostoma spp)、血管圆线虫属种(Angiostrongylus spp.)、异尖线虫属种(Anisakis spp.)、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.)、布鲁格氏丝虫属种(Brugia spp.)、仰口线虫属种(Bunostomum spp.)、毛细线虫属种(Capillaria spp.)、夏氏线虫属种(Chabertia spp.)、支睾吸虫属种(Clonorchis spp.)、古柏线虫属种(Cooperia spp.)、环体线虫属种(Crenosoma spp.)、杯口线虫属种(Cyathostoma spp.)、双腔吸虫属种(Dicrocoelium spp.)、网尾线虫属种(Dictyocaulus spp.)、裂头绦虫属种(Diphyllobothrium spp.)、复孔绦虫属种(Dipylidium spp.)、恶丝虫属种(Dirofilariaspp.)、龙线虫属种(Dracunculus spp.)、棘球绦虫属种(Echinococcus spp.)、棘口吸虫属种(Echinostoma spp.)、蛲虫属种(Enterobius spp.)、真鞘线虫属种(Eucoleus spp.)、片吸虫属种(Fasciola spp.)、拟片吸虫属种(Fascioloides spp.)、姜片虫属种(Fasciolopsis spp.)、类丝线虫属种(Filaroides spp.)、筒线虫属种(Gongylonemaspp.)、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(Heterakisspp.)、膜壳绦虫属种(Hymenolepis spp.)、猪圆线虫属种(Hyostrongylus spp.)、光丝虫属种(Litomosoides spp.)、罗阿丝虫属种(Loa spp.)、后圆线虫属种(Metastrongylusspp.)、次睾吸虫属种(Metorchis spp.)、中殖孔绦虫属种(Mesocestoides spp.)、蒙尼茨绦虫属种(Moniezia spp.)、缪勒线虫属种(Muellerius spp.)、板口线虫属种(Necatorspp.)、细颈线虫属种(Nematodirus spp.)、日圆线虫属种(Nippostrongylus spp.)、结节线虫属种(Oesophagostomum spp.)、Ollulanus属种、盘尾丝虫属种(Onchocerca spp)、后睾吸虫属种(Opisthorchis spp.)、奥斯勒丝虫属种(Oslerus spp.)、胃线虫属种(Ostertagia spp.)、尖尾线虫属种(Oxyuris spp.)、Paracapillaria属种、副丝虫属种(Parafilaria spp.)、并殖吸虫属种(Paragonimus spp.)、同盘吸虫属种(Paramphistomumspp.)、副裸头绦虫属种(Paranoplocephala spp.)、副蛔虫属种(Parascaris spp.)、Passalurus属种、原圆线虫属种(Protostrongylus spp.)、裂体吸虫属种(Schistosomaspp.)、鬃丝虫属种(Setaria spp.)、Spirocerca属种、冠丝虫属种(Stephanofilariaspp.)、冠线虫属种(Stephanurus spp.)、类圆线虫属种(Strongyloides spp.)、圆线虫属种(Strongylus spp.)、比翼线虫属种(Syngamus spp.)、绦虫属种(Taenia spp.)、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.)、毛血吸虫属种(Trichobilharzia spp.)、毛圆线虫属种(Trichostrongylus spp.)、鞭虫属种(Trichurisspp.)、钩虫属种(Uncinaria spp.)、吴策线虫属种(Wuchereria spp.);
来自线虫动物门(Nematoda)的植物害虫,即植物寄生性线虫,尤其是野外垫刃线虫属种(Aglenchus spp.)(例如居农野外垫刃线虫(Aglenchus agricola))、粒线虫属种(Anguina spp.)(例如小麦粒线虫(Anguina tritici))、滑刃线虫属种(Aphelenchoidesspp.)(例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoidesfragariae))、刺线虫属种(Belonolaimus spp.)(例如细小刺线虫(Belonolaimusgracilis)、长尾刺线虫(Belonolaimus longicaudatus)、诺顿刺线虫(Belonolaimusnortoni))、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.)(例如瘟疫坏死线虫(Cacopaurus pestis))、小环线虫属种(Criconemella spp.)(例如弯曲小环线虫(Criconemella curvata)、刻线小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemella ornata)、Criconemella rusium、薄叶小环线虫(Criconemella xenoplax(=环腐线虫(Mesocriconema xenoplax))))、小环线虫属种(Criconemoides spp.)(例如Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum)、双垫刃属种(Ditylenchus app.)(例如续断双垫刃线虫(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))、半小环线虫属种(Hemicriconemoides spp.)、鞘线虫属种(Hemicycliophora spp.)、异皮线虫属种(Heterodera spp.)(例如燕麦胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heteroderaglycines)、甜菜胞囊线虫(Heterodera schachtii))、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.)、拟滑刃线虫属种(Paraphelenchus spp.)、拟毛刺线虫属种(Paratrichodorus spp.)(例如次拟毛刺线虫(Paratrichodorus minor))、短体线虫属种(Pratylenchus spp.)(例如穿刺短体线虫(Pratylenchus penetrans))、Pseudohalenchus属种、平滑垫刃属种(Psilenchus spp.)、斑皮球异皮线虫属种(Punctodera spp.)、五沟线虫属种(Quinisulcius spp.)、穿孔线虫属种(Radopholus spp.)(例如柑桔穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis))、肾状线虫属种(Rotylenchulus spp.)、盘旋线虫属种(Rotylenchus spp.)、盾线虫属种(Scutellonemaspp.)、小麦根瘿线虫属种(Subanguina spp.)、毛刺线虫属种(Trichodorus spp.)(例如短粗根毛刺线虫(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(Tylenchorhynchusannulatus))、麦线虫属种(Tylenchulus spp.)(例如柑桔根线虫(Tylenchulussemipenetrans))、剑线虫属种(Xiphinema spp.)(例如标准剑线虫(Xiphinema index));
此外,还可防治来自原生动物(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”包括线虫门的所有物种以及特别是本文中作为寄生虫作用于植物或真菌(例如滑刃目(Aphelenchida)、根结线虫、垫刃目(Tylenchida)及其他目的物种)或者人体和动物(例如毛线虫目(Trichinellida)、垫刃目、小杆目(Rhabditida)和旋尾目(Spirurida)的物种)并且在这些活体内或上造成侵害的物种、以及其它寄生蠕虫。
如本文中所述,在作物保护中的杀线虫剂能防治线虫。
术语“防治线虫”意指杀死线虫或者预防或阻止它们的发育或它们的生长或者预防或阻止它们侵入植物组织中或它们吸食植物组织。
在本文中,化合物的功效通过下列方式来确定:在用式(I)的化合物处理过的植物或植物部位或处理过的土壤与未处理的植物或植物部位或未经处理的土壤(100%)之间比较死亡率、瘿的形成、孢囊的形成、每体积土壤的线虫密度、每株根部的线虫密度、每体积土壤的线虫卵数量、线虫的运动性。优选地,相对于未处理的植物、植物部位或未处理的土壤,所得的减少量为25-50%,特别优选51-79%以及非常特别优选通过80至100%的减少量完全杀死线虫或完全预防线虫的发育和生长。如上所述的线虫的防治还包括线虫繁殖(胞囊和/或卵的发育)的防治。式(I)的化合物还可以用于保持植物或动物健康,并且它们还可以治疗性地、预防性地或全身性地用于防治线虫。
本领域技术人员熟知用于确定死亡率、瘿的形成、孢囊的形成、每体积土壤的线虫密度、每株根部的线虫密度、每体积土壤的线虫卵数量、线虫的运动性的方法。
式(I)的化合物的用途可保持植物健康并且还包括减少由线虫引起的侵害和提高采收产量。
在本文中,术语“线虫”指植物线虫,其包括侵害植物的所有线虫。植物线虫包括植物寄生线虫和土传线虫。植物寄生线虫包括外寄生虫,例如剑线虫属种(Xiphinema spp.)、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.);移栖的内寄生虫,例如短体线虫属种(Pratylenchusspp.)、内侵线虫属种(Radopholus spp.)和盾线虫属种(Scutellonema spp.);非移栖的寄生虫,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.);以及茎和叶的内寄生虫,例如双垫刃属种(Ditylenchusspp.)、滑刃线虫属种(Aphelenchoides spp.)和潜根线虫属种(Hirschmaniella spp.)。破坏性的寄生在根部的土壤线虫优选为,例如,异皮线虫属种或球形球异皮线虫属种的胞囊形成的线虫,和/或根结线虫属种的根瘿线虫。这些属种的破坏性的物种为,例如,南方根结线虫(Meloidogyne incognita)、大豆异皮线虫(Heterodera glycines)(大豆胞囊线虫)、马铃薯白线虫(Globodera pallida)和马铃薯金线虫(Globodera rostochiensis)(黄色马铃薯胞囊线虫),这些物种通过本文中所述的化合物进行有效地防治。然而,本文中所述的化合物的用途在任何情况下都不限于这些属种或物种,并且以相同的方式延伸至其它线虫。
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 fragariae))以及滑刃线虫属种(Aphelenchoides spp.)的茎和叶的内寄生虫;细小刺线虫(Belonolaimus gracilis)、长尾刺线虫(Belonolaimuslongicaudatus)、诺顿刺线虫(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)以及伞滑刃线虫属种(Bursaphelenchus spp.);瘟疫坏死线虫(Cacopaurus pestis);弯曲小环线虫(Criconemella curvata)、刻线小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemella ornata)、Criconemellarusium、薄叶小环线虫(Criconemella xenoplax)(=环腐线虫(Mesocriconemaxenoplax))以及小环线虫属种(Criconemella spp.)、Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum以及小环线虫属种(Criconemoidesspp.);腐烂茎线虫(Ditylenchus destructor)、续断双垫刃线虫(Ditylenchus dipsaci)、食菌茎线虫(Ditylenchus myceliophagus)以及双垫刃属种(Ditylenchus spp.)的茎和叶的内寄生虫;异头锥线虫(Dolichodorus heterocephalus);马铃薯白线虫(Globoderapallida)(=马铃薯胞囊线虫(Heterodera pallida))、马铃薯金线虫(Globoderarostochiensis)(黄色马铃薯胞囊线虫(yellow potato cyst nematode))、Globoderasolanacearum、烟草孢囊线虫(Globodera tabacum)、佛吉亚球胞囊线虫(Globoderavirgini)以及异皮线虫属种(Globodera spp.)的非移栖的胞囊形成的寄生虫;双角螺旋线虫(Helicotylenchus digonicus)、双宫螺旋线虫(Helicotylenchus dihystera)、刺桐双角螺旋线虫(Helicotylenchus erythrine)、香蕉螺旋线虫(Helicotylenchusmulticinctus)、短小双角螺旋线虫(Helicotylenchus nannus)、壮螺旋线虫(Helicotylenchus pseudorobustus)以及螺旋线虫属种(Helicotylenchus spp.);半小环线虫(Hemicriconemoides);蚤缀鞘线虫(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)和异皮线虫属种的非移栖的孢囊形成的寄生虫;纤细潜根线虫(Hirschmaniella gracilis)、水稻潜根线虫(Hirschmaniella oryzae)、棘尾赫希曼线虫(Hirschmaniella spinicaudata)和潜根线虫属种(Hirschmaniella spp.)的茎和叶的内寄生虫;埃及纽带线虫(Hoplolaimus aegyptii)、Hoplolaimus californicus、哥伦比亚纽带线虫(Hoplolaimus columbus)、帽状纽带线虫(Hoplolaimus galeatus)、印度纽带线虫(Hoplolaimus indicus)、大针纽带线虫(Hoplolaimus magnistylus)、不强纽带线虫(Hoplolaimus pararobustus)、非洲长针线虫(Longidorus africanus)、短环长针线虫(Longidorus breviannulatus)、延伸长针线虫(Longidorus elongatus)、光头长针线虫(Longidorus laevicapitatus)、藤蔓长针线虫(Longidorus vineacola)和长针线虫属种的外寄生虫;高粱根结线虫(Meloidogyne acronea)、非洲根结线虫(Meloidogyneafricana)、花生根结线虫(Meloidogyne arenaria)、Meloidogyne arenaria thamesi、甘兰根结线虫(Meloidogyne artiella)、奇氏根结线虫(Meloidogyne chitwoodi)、Meloidogyne coffeicola、埃塞俄比亚根结线虫(Meloidogyne ethiopica)、短小根结线虫(Meloidogyne exigua)、大叶含笑根结线虫(Meloidogyne fallax)、禾草根结线虫(Meloidogyne graminicola)、禾本科根结线虫(Meloidogyne graminis)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、原生南方根结线虫(Meloidogyne incognita acrita)、爪哇根结线虫(Meloidogyne javanica)、吉库尤根结线虫(Meloidogyne kikuyensis)、微小根结线虫(Meloidogyne minor)、纳西根结线虫(Meloidogyne naasi)、巴拉那根结线虫(Meloidogyne paranaensis)、泰晤士根结线虫(Meloidogyne thamesi)和根结线虫属的非移栖的寄生虫;瓢线虫属种(Meloinema spp.)、异常科布线虫(Nacobbus aberrans)、Neotylenchus vigissi、Paraphelenchuspseudoparietinus、葱拟毛刺线虫(Paratrichodorus allius)、裂片拟毛刺线虫(Paratrichodorus lobatus)、微小拟毛刺线虫(Paratrichodorus minor)、矮小拟毛刺线虫(Paratrichodorus nanus)、胼胝拟毛刺线虫(Paratrichodorus porosus)、光滑拟毛刺线虫(Paratrichodorus teres)和拟毛刺线虫属种(Paratrichodorus spp.);钩针线虫(Paratylenchus hamatus)、不显著针线虫(Paratylenchus minutus)、突出针线虫(Paratylenchus projectus)和针线虫属种(Paratylenchus spp.);敏捷短体线虫(Pratylenchus agilis)、艾氏短体线虫(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)、德式短体线虫(Pratylenchus delattrei)、圆尾短体线虫(Pratylenchus giibbicaudatus)、古氏短体线虫(Pratylenchus goodeyi)、钩状短体线虫(Pratylenchus hamatus)、六纹短体线虫(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)、斯氏短体线虫(Pratylenchus scribneri)、精美短体线虫(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)和短体线虫属种的移栖的内寄生虫;Pseudohalenchus minutus、大齿平滑垫刃线虫(Psilenchus magnidens)、肿大平滑垫刃线虫(Psilenchus tumidus)、查尔斑皮线(Punctodera chalcoensis)、尖锐五沟线虫(Quinisulcius acutus)、柑橘穿孔线虫(Radopholus citrophilus)、相似穿孔线虫(Radopholus similis)、穿孔线虫属种的移栖的内寄生虫;北方肾型线虫(Rotylenchulus borealis)、微小肾型线虫(Rotylenchulusparvus)、肾形小环线虫(Rotylenchulus reniformis)和肾型线虫属种(Rotylenchulusspp.);直沟盘旋线虫(Rotylenchus laurentinus)、Rotylenchus macrodoratus、强壮盘旋线虫(Rotylenchus robustus)、单型盘旋线虫(Rotylenchus uniformis)和宽泛的盘旋线虫属种(Rotylenchus spp.);小尾盾线虫(Scutellonema brachyurum)、缓慢盾线虫(Scutellonema bradys)、格尾盾线虫(Scutellonema clathricaudatum)和盾线虫属种(Scutellonema spp.)的移栖的内寄生虫;根瘿亚蟃线虫(Subanguina radiciola)、Tetylenchus nicotianae、圆筒毛刺线虫(Trichodorus cylindricus)、微小毛刺线虫(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)、少见毛刺线虫(Trichodorus sparsus)和毛刺线虫属种的外寄生虫;农田矮化线虫(Tylenchorhynchusagri)、菜蔬矮化线虫(Tylenchorhynchus brassicae)、清亮矮化线虫(Tylenchorhynchusclarus)、克莱顿矮化线虫(Tylenchorhynchus claytoni)、指状矮化线虫(Tylenchorhynchus digitatus)、伊布里矮化线虫(Tylenchorhynchus ebriensis)、最大矮化线虫(Tylenchorhynchus maximus)、裸矮化线虫(Tylenchorhynchus nudus)、普通矮化线虫(Tylenchorhynchus vulgaris)和矮化线虫属种(Tylenchorhynchus spp.);柑桔根线虫(Tylenchulus semipenetrans)和小垫刃线虫属种的半寄生虫;美洲剑线虫(Xiphinema americanum)、短颈剑线虫(Xiphinema brevicolle)、Xiphinemadimorphicaudatum、标记剑线虫(Xiphinema index)和剑线虫属种(Xiphinema spp.)的外寄生虫。
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);茎线虫属的线虫,例如马铃薯腐烂线虫(马铃薯茎线虫(Ditylenchus destructor))以及茎和球茎线虫(续断双垫刃线虫(Ditylenchus dipsaci));短体线虫(Pratylenchus)属的线虫,如玉米根腐线虫(穿刺短体线虫(Pratylenchus penetrans))、菊花根腐线虫(伪短体线虫(Pratylenchusfallax))、咖啡根腐线虫(咖啡短体线虫(Pratylenchus coffeae))、茶树根腐线虫(卢斯短体线虫(Pratylenchus loosi))和胡桃根腐线虫(伤残短体线虫(Pratylenchus vulnus));球异皮线虫属(Globodera)的线虫,如黄色马铃薯孢囊线虫(马铃薯金线虫(Globoderarostochiensis))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,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,如稻干尖线虫(贝西拟滑刃线虫(Aphelenchoides besseyi))、菊叶线虫(菊叶芽滑刃线虫(Aphelenchoides ritzemabosi))和草莓线虫(草莓滑刃线虫(Aphelenchoidesfragariae));真滑刃线虫属(Aphelenchus)的线虫,如食菌线虫(燕麦真滑刃线虫(Aphelenchus avenae));穿孔线虫属(Radopholus)的线虫,如掘穴线虫(相似穿孔线虫(Radopholus similis));半穿刺线虫属(Tylenchulus)的线虫,如柑橘根线虫(柑橘半穿刺线虫(Tylenchulus semipenetrans));肾状线虫属(Rotylenchulus)的线虫,如肾形线虫(肾形肾状线虫(Rotylenchulus reniformis));存在于树木中的线虫,如松木线虫(松材线虫(Bursaphelenchus xylophilus))和红环线虫(椰子伞滑刃线虫(Bursaphelenchuscocophilus))等。
可使用式(I)的化合物来保护的植物包括下列植物:例如谷类(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/果类(苹果、柑橘类、梨、葡萄、桃、日本杏、樱桃、胡桃、苦扁桃、香蕉、草莓等)、蔬菜类(甘蓝、番茄、菠菜、茎椰菜、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)、用作工业原料的植物(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)、葫芦科(南瓜、黄瓜、西瓜、甜瓜等)、牧草植物(鸭茅草、高粱、梯牧草(thimosy-grassa)、三叶草、紫花苜蓿(alfalfa)等)、草坪草(结缕草、剪股颖等)、香料植物(熏衣草、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、咖啡短体线虫、短小根结线虫、南方根结线虫、咖啡根结线虫、螺旋线虫属以及巴拉那根结线虫、肾状线虫属种、剑线虫属种、矮化线虫属种、盾线虫属种。
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、斯氏短体线虫、穿刺短体线虫、咖啡短体线虫、续断双垫刃线虫以及艾氏短体线虫、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、精美短体线虫、索氏短体线虫、伤残短体线虫、长尾刺线虫、圆筒毛刺线虫、原始毛刺线虫、邻近毛刺线虫、相似毛刺线虫、少见毛刺线虫、微小拟毛刺线虫、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、爪哇根结线虫、异常科布线虫、马铃薯金线虫、马铃薯白线虫、马铃薯腐烂茎线虫、相似穿孔线虫、肾形肾状线虫、Neotylenchus vigissi、假墙草异滑刃线虫(Paraphelenchus pseudoparietinus)、草莓滑刃线虫和瓢线虫属种(Meloinema spp.)。
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、斯氏短体线虫、伤残短体线虫、微小拟毛刺线虫、短小根结线虫、异常科布线虫、茄球异皮线虫、异头锥线虫(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、肾形肾状线虫以及索氏短体线虫。
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、微小拟毛刺线虫以及最短尾短体线虫、德式短体线虫、六裂短体线虫、穿刺短体线虫、玉米短体线虫、细小刺线虫、诺顿刺线虫(Belonolaimus nortoni)、短环长针线虫、花生根结线虫、Meloidogynearenariathamesi、禾本科根结线虫、南方根结线虫、Meloidogyne incognitaacrita、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、续断双垫刃线虫、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、异头锥线虫(Dolichodorusheterocephalus)、装饰小环线虫、俄尼小环线虫、相似穿孔线虫、北方肾状线虫、微小肾状线虫、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、普通矮化线虫、尖锐五沟线虫、微小针线虫、微细鞘线虫、土壤粗纹膜垫线虫、小麦粒瘿线虫、花生滑刃线虫、小尾盾线虫和根瘿亚蟃线虫。
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、斯氏短体线虫、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、艾氏短体线虫、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、裂片拟毛刺线虫(Paratrichodorus lobatus)、毛刺线虫属种、花生根结线虫、北方根结线虫、烟草球异皮线虫、茄球异皮线虫、弗吉尼亚球异皮线虫、续断双垫刃线虫、肾状线虫属种、螺旋线虫属种、美洲剑线虫、小环线虫属种(Criconemoides spp.)、肾形肾状线虫、克莱顿矮化线虫、短体线虫属种(Pratylenchus spp.)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、微小拟毛刺线虫、多孔拟毛刺线虫、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(Rotylenchusmacrodoratus)、美洲剑线虫、短颈剑线虫、标准剑线虫、小环线虫属种、半小环线虫属、相似穿孔线虫和嗜柑橘穿孔线虫、花生鞘线虫、Hemicycliophora nudata和半穿刺线虫。
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、相似穿孔线虫以及圆尾短体线虫、卢斯短体线虫、根结线虫属种、多带螺旋线虫、双宫螺旋线虫和肾状线虫属种。
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、古氏短体线虫、根结线虫属种、肾形肾状线虫以及逃逸长针线虫、光头长针线虫(Longidorus laevicapitatus)、原始毛刺线虫、微小毛刺线虫、异皮线虫属种、食菌茎线虫、加利福尼亚纽带线虫、拟强壮纽带线虫、印度纽带线虫、双宫螺旋线虫、短小螺旋线虫、多带螺旋线虫、刺桐螺旋线虫、双形尾剑线虫、相似穿孔线虫、指状矮化线虫、伊布里矮化线虫、微小针线虫、格尾盾线虫、缓慢盾线虫、尾粗裸矛线虫、Psilenchus magnidens、Pseudohalenchus minutus、弗尼亚小环线虫、俄尼小环线虫和畸形小环线虫。
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、斯氏短体线虫、落选短体线虫、最短尾短体线虫、索氏短体线虫和半穿刺线虫。
式(I)的化合物特别适用于防治树木作物——仁果类线虫,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——核果类线虫,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、斯氏短体线虫、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、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、甘蔗和稻类的线虫,特别是毛刺线虫属种、小环线虫属种(Criconemella spp.)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Cacopauruspestis。
在本文中,术语“线虫”还指侵害人或动物的线虫。
对人或动物有害的具体线虫种类为:
毛形亚目(Trichinellida)的线虫,例如,鞭虫属种(Trichuris spp.)、毛细线虫属种(Capillaria spp.)、Paracapillaria属种、真鞘线虫属种(Eucoleus spp.)、Trichomosoides属种、毛线虫属种(Trichinella spp.);
垫刃目(Tylenchida)的线虫,例如,微线虫属种(Micronema spp.)、粪圆线虫属种(Strongyloides spp.);
小杆亚目(Rhabditina)的线虫,例如,圆线虫属种(Strongylus spp.)、三齿线虫属种(Triodontophorus spp.)、食管齿线虫属种(Oesophagodontus spp.)、毛线线虫属种(Trichonema spp.)、辐首线虫属种(Gyalocephalus spp.)、柱咽线虫属种(Cylindropharynx spp.)、杯口线虫属种(Poteriostomum spp.)、Cyclococercus属种、杯冠线虫属种(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(Ancylostomaspp.)、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(Syngamusspp.)、盅口线虫属种(Cyathostoma spp.)、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.)、囊尾属种(Cystocaulusspp.)、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(Angiostrongylus spp.)、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(Ostertagiaspp.)、背带丝虫属种(Teladorsagia spp.)、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.)、猪圆形线虫属种(Hyostrongylus spp.)、尖柱线虫属种(Obeliscoides spp.)、裂口线虫属种(Amidostomumspp.)、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.)、尤线虫属种(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.)、布鲁丝虫属种(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,并因此用于防治蠕虫——不一定属于线虫类——其是人体和动物中的寄生虫。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(例如单殖亚纲(Monogenea)、绦虫(cestodes)和吸虫(trematodes))、棘头动物门(Acanthocephala)和舌形虫属种(Pentastoma)。可优选提及下列蠕虫:
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: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(Diplogonoporusspp.);
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.)、燧体绦虫属种(Thysanosmsa 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.)、Anhyra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(Hydratigera spp.)、戴文氏绦虫属种(Davainea spp.)、瑞列绦虫属种(Raillietina spp.)、膜壳绦虫属种(Hymenolepsis spp.)、棘鳞绦虫属种(Echinolepsis 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(Joyeuxiella spp.)、复孔绦虫属种(Diplopylidium spp.)。
吸虫:复殖亚纲(Digenea),例如,双穴吸虫属种(Diplostomum spp.)、茎穴吸虫属种(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(Typhloccelum spp.)、同端盘吸虫属种(Paramphistomum spp.)、杯殖吸虫属种(Calicophoron spp.)、殖盘吸虫属种(Cotylphoron 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(Prosthogonismus 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.);
棘头虫纲: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(Linguatulaspp.)。
在兽医学领域和动物饲养中,式(I)的化合物的给药以合适的制剂形式通过本领域广泛已知的方法直接或经肠内、经肠胃外、经皮或经鼻进行。给药可以是预防性的或治疗性的。
在某些浓度或施用率下,式(I)的化合物还可以任选地用作除草剂、安全剂、生长调节剂或改进植物特性的试剂,用作杀微生物剂和杀配子剂,例如用作杀真菌剂、抗真菌剂、杀细菌剂、杀病毒剂(例如抵抗类病毒的试剂)或用作抵抗MLO(类支原体生物)和/或RLO(类立克次氏体生物)的试剂。若合适的话,它们还可以用作用于合成其它活性化合物的中间体或前体。
制剂
本发明还涉及作为农药的制剂和由其制备的使用形式(例如浸液、滴液和喷雾液体),其包含至少一种式(I)的化合物。在一些情况下,所述使用形式包含其他农药和/或改善作用的佐剂,如渗透剂,例如植物油(例如菜籽油、葵花油)、矿物油(例如石蜡油)、植物脂肪酸的烷基酯(例如菜籽油甲酯或大豆油甲酯)、或烷醇烷氧基化物;和/或铺展剂,例如烷基硅氧烷;和/或盐,例如有机或无机铵盐或鏻盐,例如硫酸铵或磷酸氢二铵;和/或保持促进剂,例如磺基丁二酸二辛酯或羟丙基瓜尔胶聚合物;和/或保湿剂,例如丙三醇;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)、乳液浓缩剂(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);这些制剂和其他可能的制剂类型由国际作物生命(Crop Life International)记载于下列文献中:例如《农药说明书》、《联合国粮农组织和世界卫生组织关于农药说明书的发展和使用手册》、《联合国粮农组织植物生产与保护文献-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定,2004,ISBN:9251048576)。除一种以上的式(I)的化合物之外,所述制剂还任选地包含其他农业化学活性化合物。
这些制剂或使用形式优选包含助剂,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,佐剂是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、对叶片表面的附着或渗透的试剂。
这些制剂是以已知的方式制备的,例如通过将式(I)的化合物与助剂(例如增量剂、溶剂和/或固体载体)和/或其他助剂(例如表面活性剂)进行混合来制备。所述制剂在合适的设备中制备,或在施用之前或施用过程中制备。
所用的助剂可以为适用于赋予式(I)的化合物的制剂或由这些制剂制备的使用形式(例如即用型农药,如喷雾液剂或拌种产品)以特殊的性质(例如某些物理的、技术的和/或生物学性质)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类(例如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(如果合适的话,其还可被取代、醚化和/或酯化)、酮类(例如丙酮、环己酮)、酯类(包括脂肪和油)以及(聚)醚、未取代和取代的胺、酰胺、内酰胺(例如N-烷基吡咯烷酮)以及内酯、砜和亚砜(例如二甲亚砜)。
如果所用的增量剂为水,则还可使用例如有机溶剂作为助溶剂。有用的液体溶剂主要为: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;醇类,例如丁醇或乙二醇,及其醚和酯;酮类,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基甲酰胺和二甲亚砜;以及水。
原则上,可使用所有合适的溶剂。合适的溶剂的实例为芳族烃,例如二甲苯、甲苯或烷基萘;氯代芳族烃或氯代脂族烃,例如氯苯、氯乙烯或二氯甲烷;脂族烃,例如环己烷、石蜡、石油馏分、矿物油和植物油;醇类,例如甲醇、乙醇、异丙醇、丁醇或乙二醇,及其醚和酯;酮类,例如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,例如二甲基亚砜;以及水。
原则上,可使用所有合适的载体。有用的载体尤其包括:例如,铵盐和粉碎的天然矿物,例如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土;以及粉碎的合成材料,例如细分散的二氧化硅、氧化铝及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。用于颗粒剂的有用载体包括:例如,压碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石、白云石,以及无机和有机粗粉的合成颗粒,以及有机材料的颗粒,例如锯屑、纸、椰壳、玉米穗轴及烟草秸秆。
还可使用液化的气体增量剂或溶剂。特别合适的增量剂或载体是在环境温度及大气压力下为气态的那些增量剂或载体,例如气溶胶推进剂气体,例如卤代烃、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,或这些表面活性剂的混合物的实例包括:聚丙烯酸盐;木素磺酸盐;苯酚磺酸盐或萘磺酸盐;环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺、与取代的苯酚(优选烷基酚或芳基酚)的缩聚物;磺基丁二酸酯的盐;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;以及含有硫酸盐、磺酸盐和磷酸盐的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐、蛋白质水解物、木素亚硫酸盐废液及甲基纤维素。如果式(I)的化合物中的一种和/或惰性载体中的一种不溶于水并且当施用发生在水中时,则表面活性剂的存在是有利的。
可存在于所述制剂及由其获得的使用形式中的其他助剂包括染料如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;和有机染料,例如茜素染料、偶氮染料及金属酞菁染料;以及营养素和微量营养素,例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
其它组分可为稳定剂,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。还可存在发泡剂或消泡剂。
此外,所述制剂及由其获得的使用形式还可包含作为其它助剂的粘着剂(例如羧甲基纤维素)以及以粉末、颗粒或胶乳形式的天然及合成聚合物(例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯),或天然磷脂(例如脑磷脂和卵磷脂)和合成磷脂。其他可行的助剂为矿物油和植物油。
任选地,其他助剂可存在于制剂及由其获得的使用形式中。所述添加剂的实例包括香料、保护胶体、粘结剂(binder)、粘合剂(adhesive)、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、铺展剂。一般而言,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。
有用的保持促进剂包括降低动力学表面张力的所有那些物质,例如磺基丁二酸二辛酯;或增加粘弹性的物质,例如羟丙基瓜尔胶聚合物。
在本文中,合适的渗透剂为常用于改进农业化学活性化合物向植物渗透的所有那些物质。在本文中渗透剂定义为:其从(通常为含水的)施用液剂和/或从喷雾涂层中向植物表皮中渗透从而提高活性化合物在表皮中的运动性的能力。可使用文献(Baur等人,1997,Pesticide Science 51,131-152)中记载的方法测定这种特性。实例包括醇烷氧基化物,例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);或者铵盐和/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,特别优选0.01重量%至95重量%的式(I)的化合物,更优选0.5重量%至90重量%的式(I)的化合物,基于制剂的重量计。
在由制剂(特别是农药)制备的使用形式中,式(I)的化合物的含量可在宽范围内变化。所述使用形式中的式(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%,基于所述使用形式的重量计。以适于使用形式的常规方式进行施用。
混合物
式(I)的化合物还可与一种以上的合适的杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物、有益物种、除草剂、肥料、驱鸟剂、植物强壮素(phytotonic)、止繁殖剂、安全剂、化学信息素和/或植物生长调节剂混合使用,从而例如拓宽作用谱、延长作用持续时间、增加作用速率、防止排斥或防止抗性进化。另外,这种活性化合物结合物可改进植物生长和/或对非生物因素(例如高温或低温)、干旱或高含水量或土壤盐度的耐受性。还可改进开花和结果性能、优化发芽能力和根系发育、促进采收并提高产量、影响成熟、改进采收产品的品质和/或营养价值、延长储存期限和/或改进采收产品的可加工性。
此外,式(I)的化合物可与其他活性化合物或化学信息素(例如引诱剂和/或驱鸟剂和/或植物活化剂和/或生长调节剂和/或肥料)混合存在。同样,式(I)的化合物可与改进植物特性(例如生长、采收材料的产量和品质)的试剂混合使用。
在本发明的具体的实施方案中,式(I)的化合物与其他化合物(优选下列描述的那些化合物)以混合物的形式存在于制剂或由这些制剂制备的使用形式中。
如果下述化合物的一种可以不同的互变异构的形式存在,则在每种情况下还包括这些形式,即使未明确说明。
杀昆虫剂/杀螨剂/杀线虫剂:
本文中以其通用名识别的活性化合物是已知的,并且记载于例如农药手册(“农药手册(The Pesticide Manual)”第16版,英国作物保护委员会(British Crop ProtectionCouncil)2012)中或可在网站(例如http://www.alanwood.net/pesticides)上找到。
(1)乙酰胆碱酯酶(AChE)抑制剂,例如氨基甲酸酯类,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)、灭除威(XMC)和灭杀威(xylylcarb);或有机磷酸酯类,如乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(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)、噻唑酮磷(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、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)、氧化乐果(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)、虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹噁磷(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门控氯离子通道拮抗剂,例如环二烯有机氯类,如氯丹(chlordane)和硫丹(endosulfan);或苯基吡唑类(fiproles),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-transallethrin)、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)、氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、γ-氯氟氰菊酯(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)、右旋烯炔菊酯[(EZ)-(1R)异构体](empenthrin[(EZ)-(1R)-isomers])、S-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)、咪炔菊酯(imiprothrin)、噻恩菊酯(kadethrin)、氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans-isomer])、炔丙菊酯(prallethrin)、除虫菊素(pyrethrine)(除虫菊(pyrethrum))、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(1R)-异构体](tetramethrin[(1R)-isomer])、四溴菊酯(tralomethrin)和四氟菊酯(transfluthrin);或滴滴涕(DDT);或甲氧滴滴涕(methoxychlor);
(4)烟碱能乙酰胆碱受体(nAChR)激动剂,例如新烟碱类(neonicotinoids),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);或砜虫啶(sulfoxaflor);
(5)烟碱能乙酰胆碱受体(nAChR)变构活化剂,例如多杀霉素类(spinosyns),例如乙基多杀霉素(spinetoram)和多杀菌素(spinosad);
(6)氯离子通道活化剂,例如阿维菌素类(avermectins)/米尔倍霉素类(milbemycins),如阿巴克丁(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(Juvenile hormone imitator),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)具有未知的或非特异性的作用机理的活性化合物,例如烷基卤化物,如溴甲烷和其他烷基卤化物;或氯化苦(chloropicrin);或硫酰氟(sulphurylfluoride);或硼砂(borax);或酒石酸氧锑钾(tartaremetic);
(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)昆虫肠膜的微生物干扰剂,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)、苏云金芽孢杆菌鲇泽亚种(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),和BT植物蛋白质: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);或有机锡化合物类,例如三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatinoxide);或克螨特(propargite);或四氯二苯砜(tetradifon);
(13)中断H质子梯度的氧化磷酸化解偶剂,例如虫螨腈(chlorfenapyr)、DNOC和氟虫胺(sulfluramid);
(14)烟碱能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(thiocylam)和杀虫双(thiosultap-sodium);
(15)0型几丁质生物合成抑制剂,例如双三氟虫脲(bistrifluron)、氟啶脲(chlorfluazuron)、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)和杀铃脲(triflumuron);
(16)1型几丁质生物合成抑制剂,例如噻嗪酮(buprofezin);
(17)蜕皮抑制剂(特别是用于双翅目,即双翅类),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,例如灭蚁腙(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杀螨剂类,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);
(22)电压门控钠通道阻断剂,例如茚虫威(indoxacarb)或氰氟虫胺(metaflumizone);
(23)乙酰辅酶A羧化酶抑制剂,例如,特窗酸(tetronicacid)和特特拉姆酸(tetramicacid)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,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,苯腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen);
(28)兰尼碱受体效应物,例如,二酰胺类,如氯虫酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)和氟虫酰胺(flubendiamide);
其他活性化合物,例如afidopyropen、印楝素(azadirachtin)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、冰晶石(cryolite)、三氯杀螨醇(dicofol)、氟螨嗪(diflovidazin)、氟噻虫砜(fluensulfone)、flometoquin、嘧虫胺(flufenerim)、氟菌螨酯(flufenoxystrobin)、丁虫腈(flufiprole)、氟吡菌酰胺(fluopyram)、flupyradifurone、呋喃虫酰肼(fufenozide)、氯氟醚菊酯(heptafluthrin)、氯噻啉(imidaclothiz)、异菌脲(iprodione)、氯氟醚菊酯(meperfluthrin)、哌虫啶(paichongding)、pyflubumide、敌磺酸(pyrifluquinazon)、嘧螨胺(pyriminostrobin)、四氟醚菊酯(tetramethylfluthrin)和碘甲烷;以及基于坚强芽孢杆菌(Bacillusfirmus)的制剂(I-1582,BioNeem,Votivo),和以下化合物:3-溴-N-{2-溴-4-氯-6-[(1-环丙基乙基)氨基甲酰基]苯基}-1-(3-氯吡啶-2-基)-1H-吡唑-5-甲酰胺(已知于WO2005/077934)和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-乙基碳酸酯(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)、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-{2-氧代-2-[(2,2,2-三氟乙基)氨基]乙基}苯甲酰胺(已知于WO2005/085216)、4-{5-[3-氯-5-(三氟甲基)苯基]-5-(三氟甲基)-4,5-二氢-1,2-噁唑-3-基}-N-{2-氧代-2-[(2,2,2-三氟乙基)氨基]乙基}-1-萘甲酰胺(已知于WO2009/002809)、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-乙基肼羧酸甲酯(已知于WO2005/085216)、1-(3-氯吡啶-2-基)-N-[4-氰基-2-甲基-6-(甲基氨基甲酰基)苯基]-3-{[5-(三氟甲基)-2H-四唑-2-基]甲基}-1H-吡唑-5-甲酰胺(已知于WO2010/069502)、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)、3-氯-N-(2-氰基丙烷-2-基)-N-[4-(1,1,1,2,3,3,3-七氟丙烷-2-基)-2-甲基苯基]酞酰胺(已知于WO2012/034472)、8-氯-N-[(2-氯-5-甲氧基苯基)磺酰基]-6-(三氟甲基)咪唑并[1,2-a]吡啶-2-甲酰胺(已知于WO2010/129500)、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-氧桥硫杂环丁烷-3-基)苯甲酰胺(已知于WO2009/080250)、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-氧桥硫杂环丁烷-3-基)苯甲酰胺(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-酚盐(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-酚盐(已知于WO2009/099929)、(5S,8R)-1-[(6-氯吡啶-3-基)甲基]-9-硝基-2,3,5,6,7,8-六氢-1H-5,8-环氧咪唑并[1,2-a]氮杂卓(已知于WO2010/069266)、(2E)-1-[(6-氯吡啶-3-基)甲基]-N'-硝基-2-亚戊基肼甲酰亚胺酰胺(已知于WO2010/060231)、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)。
杀真菌剂
本文中以其通用名识别的活性化合物是已知的,并且记载于例如“农药手册(ThePesticide Manual)”中或网站(例如:http://www.alanwood.net/pesticides)上。
(1)麦角固醇生物合成抑制剂,例如(1.1)杀螟丹(aldimorph)、(1.2)戊环唑(azaconazole)、(1.3)双苯三唑醇(bitertanol)、(1.4)糠菌唑(bromuconazole)、(1.5)环丙唑醇(cyproconazole)、(1.6)苄氯三唑醇(diclobutrazole)、(1.7)噁醚唑(difenoconazole)、(1.8)烯唑醇(diniconazole)、(1.9)高效烯唑醇(diniconazole-M)、(1.10)吗菌灵(dodemorph)、(1.11)吗菌灵乙酸盐(dodemorph acetate)、(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(fenhexamid)、(1.17)苯锈啶(fenpropidin)、(1.18)丁苯吗啉(fenpropimorph)、(1.19)喹唑菌酮(fluquinconazole)、(1.20)调嘧醇(flurprimidol)、(1.21)氟硅唑(flusilazole)、(1.22)粉唑醇(flutriafole)、(1.23)呋菌唑(furconazole)、(1.24)顺呋醚唑(furconazole-cis)、(1.25)己唑醇(hexaconazole)、(1.26)烯菌灵(imazalil)、(1.27)烯菌灵硫酸盐(imazalil sulfate)、(1.28)酰胺唑(imibenconazole)、(1.29)环戊唑醇(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(paclobutrazol)、(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)稗草畏(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(terbinafine)、(1.49)氟醚唑(tetraconazole)、(1.50)三唑酮(triadimefon)、(1.51)唑菌醇(triadimenol)、(1.52)克啉菌(tridemorph)、(1.53)氟菌唑(triflumizole)、(1.54)嗪氨灵(triforine)、(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-羧酸甲酯、(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-甲基酰亚氨基甲酰胺、(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}酰亚氨基甲酰胺、(1.64)邻-[1-(4-甲氧基苯氧基)-3,3-二甲基丁烷-2-基]1H-咪唑-1-硫代甲酸酯、(1.65)啶菌噁唑(pyrisoxazole);
(2)呼吸抑制剂(呼吸链抑制剂),例如(2.1)联苯吡菌胺(bixafen)、(2.2)啶酰菌胺(boscalid)、(2.3)萎锈灵(carboxin)、(2.4)二氟林(diflumetorim)、(2.5)甲呋酰胺(fenfuram)、(2.6)氟吡菌酰胺(fluopyram)、(2.7)氟酰胺(flutolanil)、(2.8)氟唑菌酰胺(fluxapyroxad)、(2.9)呋吡菌胺(furametpyr)、(2.10)拌种胺(furmecyclox)、(2.11)吡唑萘菌胺(顺式差向异构外消旋体1RS、4SR、9RS和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)、(2.13)吡唑萘菌胺(反式差向异构外消旋体1R、4S、9S)、(2.14)吡唑萘菌胺(反式差向异构外消旋体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(顺式差向异构外消旋体1R、4S、9R)、(2.17)吡唑萘菌胺(顺式差向异构外消旋体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-甲氧基丙烷-2-基]-3-(二氟甲基)-1-甲基l-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-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基l-1H-吡唑-4-甲酰胺、和(2.31)N-[(1R,4S)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-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-[(1R)-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-[(1S)-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l-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l-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)isofetamid;
(3)作用在呼吸链的复合物-III的呼吸抑制剂(呼吸链抑制剂),例如,(3.1)唑嘧菌胺(ametoctradin)、(3.2)安美速(amisulbrom)、(3.3)嘧菌酯(azoxystrobin)、(3.4)氰霜唑(cyazofamid)、(3.5)甲香菌酯(coumethoxystrobin)、(3.6)丁香菌酯(coumoxystrobin)、(3.7)醚菌胺(dimoxystrobin)、(3.8)烯肟菌酯(enestroburin)、(3.9)噁唑菌酮(famoxadone)、(3.10)咪唑菌酮(fenamidone)、(3.11)氟菌螨酯(flufenoxystrobin)、(3.12)氟嘧菌酯(fluoxastrobin)、(3.13)亚胺菌(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)(2E)-2-{2-[({[(2E,3E)-4-(2,6-二氯苯基)丁-3-烯-2-基亚基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.28)2-氯-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)吡啶-3-甲酰胺、(3.29)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、(3.30)(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-2-烯酸甲酯、(3.31)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、(3.32)2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺;
(4)有丝分裂和细胞分裂抑制剂,例如(4.1)苯菌灵(benomyl)、(4.2)多菌灵(carbendazim)、(4.3)氯苯咪唑(chlorfenazole)、(4.4)乙霉威(diethofencarb)、(4.5)噻唑菌胺(ethaboxam)、(4.6)氟吡菌胺(fluopicolid)、(4.7)麦穗宁(fuberidazole)、(4.8)戊菌隆(pencycuron)、(4.9)噻苯咪唑(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)具有多位点活性的化合物,例如,(5.1)波尔多液混合物(bordeaux mixture)、(5.2)敌菌丹(captafol)、(5.3)克菌丹(captan)、(5.4)百菌清(chlorothalonil)、(5.5)铜制剂如氢氧化铜、(5.6)环烷酸铜(copper naphthenate)、(5.7)氧化铜、(5.8)氧氯化铜(copper oxychloride)、(5.9)硫酸铜(copper sulfate)、(5.10)抑菌灵(dichlofluanid)、(5.11)二噻农(dithianon)、(5.12)多果定(dodine)、(5.13)多果定游离碱(dodine freebase)、(5.14)福美铁(ferbam)、(5.15)氟灭菌丹(fluorofolpet)、(5.16)灭菌丹(folpet)、(5.17)双胍盐(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(zincmetiram)、(5.27)喹啉铜(copper-oxine)、(5.28)丙烷脒(propamidine)、(5.29)甲基代森锌(propineb)、(5.30)硫和硫制剂如多硫化钙、(5.31)福美双(thiram)、(5.32)对甲抑菌灵(tolylfluanid)、(5.33)代森锌(zineb)、(5.34)福美锌(ziram)和(5.35)敌菌灵(anilazine);
(6)抗性诱导剂,例如,(6.1)苯并噻二唑(acibenzolar-S-methyl)、(6.2)异噻菌胺(isotianil)、(6.3)噻菌灵(probenazole)、(6.4)噻酰菌胺(tiadinil)和(6.5)海带多糖(laminarin);
(7)氨基酸和蛋白质生物合成抑制剂,例如,(7.1)胺扑灭(andoprim)、(7.2)灭瘟素(blasticidin-S)、(7.3)环丙嘧啶(cyprodinil)、(7.4)春雷霉素(kasugamycin)、(7.5)春雷霉素盐酸盐水合物(kasugamycin hydrochloride hydrate)、(7.6)嘧菌胺(mepanipyrim)、(7.7)嘧霉胺(pyrimethanil)、(7.8)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉和(7.9)土霉素(oxytetracycline)和(7.10)链霉素(streptomycin);
(8)ATP生成抑制剂,例如,(8.1)薯瘟锡(fentin acetate)、(8.2)三苯锡氯(fentin chloride)、(8.3)毒菌锡(fentin hydroxide)、(8.4)噻菌胺(silthiofam);
(9)细胞壁合成抑制剂,例如(9.1)苯噻菌胺(benthiavalicarb)、(9.2)烯酰吗啉(dimethomorph)、(9.3)氟吗啉(flumorph)、(9.4)缬霉威(iprovalicarb)、(9.5)双炔酰菌胺(mandipropamid)、(9.6)多抗霉素(polyoxins)、(9.7)保粒霉素(polyoxorim)、(9.8)井冈霉素A(validamycin A)、(9.9)霜霉灭(valifenalate)和(9.10)多氧菌素B(polyoxinB);
(10)脂类和膜合成抑制剂,例如,(10.1)联苯、(10.2)地茂散(chloroneb)、(10.3)氯硝胺(dicloran)、(10.4)克瘟散(edifenphos)、(10.5)土菌灵(etridiazole)、(10.6)依杜卡(iodocarb)、(10.7)异稻瘟净(iprobenfos)、(10.8)稻瘟灵(isoprothiolane)、(10.9)霜霉威(propamocarb)、(10.10)霜霉威盐酸盐(propamocarb hydrochloride)、(10.11)胺丙威(prothiocarb)、(10.12)吡菌磷(pyrazophos)、(10.13)五氯硝基苯(quintozene)、(10.14)四氧硝基苯(tecnazene)和(10.15)甲基立枯磷(tolclofos-methyl);
(11)黑色素生物合成抑制剂,例如(11.1)加普胺(carpropamid)、(11.2)双氯氰菌胺(diclocymet)、(11.3)稻瘟酰胺(fenoxanil)、(11.4)四氯苯酞(fthalide)、(11.5)咯喹酮(pyroquilon)、(11.6)三环唑(tricyclazole)、(11.7)2,2,2-三氟乙基{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁烷-2-基}氨基甲酸酯;
(12)核酸合成抑制剂,例如,(12.1)苯霜灵(benalaxyl)、(12.2)高效苯霜灵(benalaxyl-M)(kiralaxyl)、(12.3)磺酸丁嘧啶(bupirimate)、(12.4)柯罗泽尔昆(clozylacon)、(12.5)甲菌定(dimethirimol)、(12.6)乙菌定(ethirimol)、(12.7)呋霜灵(furalaxyl)、(12.8)噁霉灵(hymexazol)、(12.9)甲霜灵(metalaxyl)、(12.10)高效甲霜灵(metalaxyl-M)(mefenoxam)、(12.11)甲呋酰胺(ofurace)、(12.12)噁霜灵(oxadixyl)、(12.13)噁喹酸(oxolinic acid)和(12.14)辛噻酮(octhilinone);
(13)信号转导抑制剂,例如,(13.1)乙菌利(chlozolinate)、(13.2)拌种咯(fenpiclonil)、(13.3)咯菌腈(fludioxonil)、(13.4)异菌脲(iprodione)、(13.5)腐霉利(procymidone)、(13.6)喹氧灵(quinoxyfen)、(13.7)乙烯菌核利(vinclozolin)和(13.8)丙氧喹啉(proquinazid);
(14)解偶剂,例如,(14.1)乐杀螨(binapacryl)、(14.2)敌螨普(dinocap)、(14.3)嘧菌腙(ferimzone)、(14.4)氟啶胺(fluazinam)和(14.5)消螨多(meptyldinocap);
(15)其他化合物,例如,(15.1)苯噻硫氰(benthiazole)、(15.2)3-苯并[b]噻吩-2-基-5,6-二氢-1,4,2-噻嗪-4-氧化物(bethoxazine)、(15.3)卡巴西霉素(capsimycin)、(15.4)香芹酮(carvone)、(15.5)灭螨猛(chinomethionat)、(15.6)甲氧苯啶菌(pyriofenone)(氯芬酮(chlazafenone))、(15.7)硫杂灵(cufraneb)、(15.8)环氟菌胺(cyflufenamid)、(15.9)霜脲氰(cymoxanil)、(15.10)环丙磺酰胺(cyprosulfamide)、(15.11)棉隆原粉(dazomet)、(15.12)咪菌威(debacarb)、(15.13)双氯酚(dichlorophen)、(15.14)哒菌酮(diclomezine)、(15.15)野燕枯(difenzoquat)、(15.16)野燕枯甲基硫酸盐(difenzoquat methylsulphate)、(15.17)二苯胺(diphenylamine)、(15.18)乙克霉特(EcoMate)、(15.19)胺苯吡菌酮(fenpyrazamine)、(15.20)氟联苯菌(flumetover)、(15.21)唑呋草(fluorimid)、(15.22)磺菌胺(flusulfamide)、(15.23)氟噻菌灵(flutianil)、(15.24)乙膦酸铝(fosetyl-aluminium)、(15.25)乙膦酸钙(fosetyl-calcium)、(15.26)乙膦酸钠(fosetyl-sodium)、(15.27)六氯苯(hexachlorobenzene)、(15.28)人间霉素(irumamycin)、(15.29)磺菌威(methasulfocarb)、(15.30)异硫氰酸甲酯(methyl isothiocyanate)、(15.31)苯菌酮(metrafenone)、(15.32)灭粉霉素(mildiomycin)、(15.33)游霉素(natamycin)、(15.34)二甲基二硫代氨基甲酸镍(nickeldimethyldithiocarbamate)、(15.35)酞菌酯(nitrothal-isopropyl)、(15.36)辛噻酮(octhilinone)、(15.37)奥克斯莫卡宾(oxamocarb)、(15.38)奥施康定(oxyfenthiin)、(15.39)五氯苯酚(pentachlorophenol)及其盐、(15.40)苯氧司林(phenothrin)、(15.41)磷酸及其盐、(15.42)霜霉威-乙膦酸盐(propamocarb-fosetylate)、(15.43)丙醇菌素钠(propanosine-sodium)、(15.44)丁吡吗啉(pyrimorph)、(15.45)(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、(15.46)(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、(15.47)吡咯尼林(pyrrolnitrin)、(15.48)特弗喹啉(tebufloquin)、(15.49)叶枯酞(tecloftalam)、(15.50)甲磺菌胺(tolnifanide)、(15.51)咪唑嗪(triazoxide)、(15.52)水杨菌胺(trichlamide)、(15.53)氰菌胺(zarilamid)、(15.54)(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-1,5-二氧杂环戊烷-7-基2-甲基丙酸酯、(15.55)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、(15.56)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、(15.57)1-(4-{4-[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、(15.58)1-(4-甲氧基苯氧基)-3,3-二甲基丁烷-2-基1H-咪唑-1-羧酸酯、(15.59)2,3,5,6-四氯-4-(甲基磺酰基)吡啶、(15.60)2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮、(15.61)2,6-二甲基-1H,5H-[1,4]二硫杂[2,3-c:5,6-c']二吡咯-1,3,5,7(2H,6H)-四酮、(15.62)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、(15.63)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、(15.64)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、(15.65)2-丁氧基-6-碘代-3-丙基-4H-苯并吡喃-4-酮、(15.66)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、(15.67)2-苯基苯酚及其盐、(15.68)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.69)3,4,5-三氯吡啶-2,6-二甲腈、(15.70)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(15.71)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(15.72)5-氨基-1,3,4-噻二唑-2-硫醇、(15.73)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、(15.74)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.75)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.76)5-甲基-6-辛基[1,2,4]三唑并[1,5-a]嘧啶-7-胺、(15.77)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.78)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-甲基酰亚氨基甲酰胺、(15.79)N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.80)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、(15.81)N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯烟酰胺、(15.82)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、(15.83)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘烟酰胺、(15.84)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、(15.85)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、(15.86)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-甲基酰亚氨基甲酰胺、(15.87)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-(1,2,3,4-四氢化萘-1-基)-1,3-噻唑-4-甲酰胺、(15.88)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)-1,2,3,4-四氢化萘-1-基]-1,3-噻唑-4-甲酰胺、(15.89)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)-1,2,3,4-四氢化萘-1-基]-1,3-噻唑-4-甲酰胺、(15.90){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、(15.91)吩嗪-1-羧酸、(15.92)喹啉-8-醇、(15.93)喹啉-8-醇硫酸盐(2:1)、(15.94){6-[({[(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸叔丁酯、(15.95)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、(15.96)N-(4'-氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(15.97)N-(2',4'-二氯联苯-2-基)-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(15.98)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、(15.99)N-(2',5'-二氟联苯-2-基)-1-甲基-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(15.100)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、(15.101)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、(15.102)2-氯-N-[4'-(丙-1-炔-1-基)联苯-2-基]烟酰胺、(15.103)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、(15.104)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、(15.105)3-(二氟甲基)-N-(4'-乙炔基联苯-2-基)-1-甲基-1H-吡唑-4-甲酰胺、(15.106)N-(4'-乙炔基联苯-2-基)-5-氟-1,3-二甲基-1H-吡唑-4-甲酰胺、(15.107)2-氯-N-(4'-乙炔基联苯-2-基)烟酰胺、(15.108)2-氯-N-[4'-(3,3-二甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.109)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、(15.110)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、(15.111)2-氯-N-[4'-(3-羟基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.112)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、(15.113)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、(15.114)2-氯-N-[4'-(3-甲氧基-3-甲基丁-1-炔-1-基)联苯-2-基]烟酰胺、(15.115)(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、(15.116)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、(15.117)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.118){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、(15.119)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)、(15.120)3,4,5-三羟基苯甲酸丙酯、(15.121)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、(15.122)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、(15.123)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、(15.124)[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、(15.125)(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、(15.126)(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、(15.127)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、(15.128)硫氰酸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-基酯、(15.129)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、(15.130)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.131)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、(15.132)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、(15.133)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、(15.134)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、(15.135)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、(15.136)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、(15.137)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.138)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.139)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.140)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.141)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.142)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.143)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.144)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚烷-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(15.145)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、(15.146)2-(6-苄基吡啶-2-基)喹唑啉、(15.147)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.148)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.149)脱落酸(abscisic acid)、(15.150)3-(二氟甲基)-N-甲氧基-1-甲基-N-[1-(2,4,6-三氯苯基)丙烷-2-基]-1H-吡唑-4-甲酰胺、(15.151)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-甲基酰亚氨基甲酰胺、(15.152)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-甲基酰亚氨基甲酰胺、(15.153)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-甲基酰亚氨基甲酰胺、(15.154)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-甲基酰亚氨基甲酰胺、(15.155)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-甲基酰亚氨基甲酰胺、(15.156)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-甲基酰亚氨基甲酰胺、(15.157)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、(15.158)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、(15.159)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、(15.160)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、(15.161)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、(15.162)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、(15.163)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、(15.164)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、(15.165)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、(15.166)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、(15.167)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、(15.168)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、(15.169)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、(15.170)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、(15.171)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、(15.172)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、(15.173)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、(15.174)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、(15.175)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、(15.176)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、(15.177)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、(15.178)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、(15.179)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、(15.180)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基酰亚氨基甲酰胺、(15.181)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-甲基酰亚氨基甲酰胺、(15.182)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。视情况而定,(1)至(15)类提及的所有混合配对体可以与合适的碱或酸形成盐,如果它们基于其官能团能够如此的话。
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、酵母菌、植物提取物和由微生物产生的包括蛋白质和次级代谢产物在内的产物。
生物农药包括诸如形成胞子的细菌、根定殖细菌的细菌以及充当生物杀昆虫剂、杀真菌剂或杀线虫剂的细菌。
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(DSM 231179);或蜡状芽孢杆菌(Bacillus cereus),具体是蜡状芽孢杆菌菌株CNCM I-1562;或者坚强芽孢杆菌(Bacillus firmus),菌株I-1582(登录号CNCMI-1582);或短小芽胞杆菌(Bacilluspumilus),具体是菌株GB34(登录号ATCC 700814)和菌株QST2808(登录号NRRL B-30087);或枯草芽孢杆菌(Bacillus subtilis),具体是菌株GB03(登录号ATCC SD-1397),或枯草芽孢杆菌菌株QST713(登录号NRRL B-21661)或枯草芽孢杆菌菌株OST 30002(登录号NRRL B-50421);苏云金芽孢杆菌(Bacillus thuringiensis),具体是苏云金芽孢杆菌以色列亚种(血清型H-14),菌株AM65-52(登录号ATCC 1276),或苏云金芽孢杆菌鲇泽亚种,具体是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌库尔斯塔克亚种菌株HD-1,或苏云金芽孢杆菌拟步行甲亚种菌株NB 176(SD-5428);侵入巴斯德氏芽菌(Pasteuria penetrans),巴斯德氏芽菌属种(Pasteuria spp.)(肾形肾状线虫(Rotylenchulus reniformis nematode))-PR3(登录号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AQ 6047(登录号NRRL30232)。
用作或可用作生物农药的真菌和酵母菌的实例为:
球孢白僵菌(Beauveria bassiana),具体是菌株ATCC 74040;盾壳霉(Coniothyrium minitans),具体是菌株CON/M/91-8(登录号DSM-9660);刀孢蜡蚧菌属种(Lecanicillium spp.),具体是菌株HRO LEC 12;蜡蚧霉(Lecanicillium lecanii),(原名为蜡蚧轮枝菌(Verticillium lecanii)),具体是菌株KV01;绿僵菌(Metarhiziumanisopliae),具体是菌株F52(DSM3884/ATCC 90448);梅奇酵母菌(Metschnikowiafructicola),具体是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现名:玫烟色棒束孢(Isaria fumosorosea)),具体是菌株IFPC 200613,或菌株阿波普卡(Apopka)97(登录号ATCC 20874);淡紫拟青霉(Paecilomyces lilacinus),具体是淡紫拟青霉菌株251(AGAL 89/030550);黄色蠕形霉(Talaromyces flavus),具体是菌株V117b;深绿木霉(Trichoderma atroviride),具体是菌株SC1(登录号CBS 122089);哈茨木霉(Trichoderma harzianum),具体是哈茨木霉(T.harzianum rifai)T39(登录号CNCM I-952)。
用作或可用作生物农药的病毒的实例为:
棉褐带卷蛾(Adoxophyes orana)(夏季水果小卷蛾(summer fruit tortrix))颗粒体病毒(GV)、苹果小卷蛾(Cydia pomonella)(苹果蠹蛾(codling moth))颗粒体病毒(GV)、棉铃虫(Helicoverpa armigera)(棉铃虫(cotton bollworm))核型多角体病毒(NPV)、甜菜夜蛾(Spodoptera exigua)(甜菜夜蛾(beet armyworm))mNPV、草地贪夜蛾(Spodoptera frugiperda)(草地粘虫(fall armyworm))mNPV、海灰翅夜蛾(Spodopteralittoralis)(美国棉树叶虫(African cotton leafworm))NPV。
还包括作为“接种剂”添加到植物或植物部位或植物器官中的细菌和真菌,并且所述细菌和真菌通过其特殊性能促进植物生长和植物健康。实例包括:
土壤杆菌属种(Agrobacterium spp.)、固氮根瘤菌(Azorhizobiumcaulinodans)、固氮螺菌属种(Azospirillum spp.)、固氮菌属种(Azotobacter spp.)、短根瘤菌属种(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)(原名为洋葱假单胞菌(Pseudomonascepacia))、巨孢囊霉属种(Gigaspora spp.)、或单包巨孢囊霉属种(Gigasporamonosporum)、球囊霉属种(Glomus spp.)、蜡蘑属种(Laccaria spp.)、布氏乳杆菌(Lactobacillus buchneri)、类球囊霉属种(Paraglomus spp.)、彩色豆马勃(Pisolithustinctorus)、假单胞菌属种(Pseudomonas spp.)、根瘤菌属种(Rhizobium spp.),尤其是三叶草根瘤菌(Rhizobium trifolii)、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产生的包括蛋白质和次级代谢产物在内的产品的实例为:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印苦楝子素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、美洲土荆芥(Chenopodium anthelminticum)、几丁质(chitin)、Armour-Zen、绵马(Dryopterisfilix-mas)、马尾草(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(奎藜籽皂甙(Chenopodium quinoa saponin)提取物)、除虫菊/除虫菊素(pyrethrum/pyrethrins)、苏里南苦树(Quassia amara)、栎(Quercus)、皂树(Quillaja)、Regalia、"RequiemTM杀昆虫剂"、鱼藤酮(rotenone)、ryania/ryanodine、西门肺草(Symphytum officinale)、艾菊(Tanacetum vulgare)、麝香草酚(thymol)、Triact 70、TriCon、大金莲花(Tropaeulummajus)、大荨麻(Urtica dioica)、藜芦定(Veratrin)、桑寄生(Viscum album)、Brassicaceae提取物,尤其是油菜籽粉或芥末。
作为混合组分的安全剂
式(I)的化合物可与安全剂结合,所述安全剂为例如解草酮(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)、解草安(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。在本文中植物理解为意指所有的植物和植物种群,例如期望和不期望的野生植物或作物植物(包括天然存在的作物植物),例如谷类(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、土豆、糖用甜菜、甘蔗、番茄、豌豆和其他蔬菜种类、棉花、烟草、油菜以及果实植物(具有下述果实:苹果、豌豆、柑橘类果实和葡萄)。作物植物可为可通过常规的育种和优化方法或者通过生物技术和基因工程方法或这些方法的组合获得的植物,包括转基因植物以及包括受植物育种者的权利保护和不保护的植物栽培种。植物部位应当理解为意指植物的所有地上和地下的部位和器官,如芽、叶、花和根,给出的实例为叶、针叶、茎、干、花、子实体、果实和种子、以及块茎、根和根茎。植物部位还包括采收的材料以及无性和有性繁殖的材料,例如插枝、块茎、根茎、分檗(slip)和种子。
根据本发明,利用式(I)的化合物来处理植物和植物部位通过常规处理方法直接进行或使所述化合物作用于其生境、环境或储存空间来进行,所述常规处理方法为例如浸润、喷洒、蒸发、雾化、散布、喷涂、注射,以及在繁殖材料的情况下,尤其是在种子的情况下,还可施用一层或更多层包衣。
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,处理野生植物物种和植物栽培种、或通过常规生物育种(如交叉或原生质体融合)获得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结合——获得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”已在上文中解释。根据本发明,特别优选分别处理市售常规栽培种或正在使用中的那些植物。植物栽培种理解为意指具有新特性(“性状”)的植物,并且其已通过常规育种、通过突变或通过重组DNA技术获得。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
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)包括通过遗传修饰接受遗传材料的所有植物,该遗传材料赋予这些植物特别有利的有用性状。这种特性的实例为:更好的植物生长、增强的对高温或低温的耐受性、增强的对干旱或对含水量或土壤盐度的耐受性、提高的开花性能、更容易采收、加速成熟、更高的产量、采收产品的更高的品质和/或更高的营养价值、采收产品的更好的储存期限和/或可加工性。这种特性的其他和特别强调的实例为增强植物对动物和微生物害虫的抗性,例如抵抗昆虫、蛛形纲动物、线虫、螨、蛞蝓以及蜗牛,例如,这是由于植物中形成的毒素、特别是通过来自苏云金芽孢杆菌的遗传材料(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c Cry2Ab、Cry3Bb和CryIF及其组合)在植物中形成的那些毒素;以及增强植物对植物病原性真菌、细菌和/或病毒的抗性,该抗性由例如系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子和抗性基因以及相应的表达蛋白和毒素引起;以及提高植物对某些除草活性化合物(例如咪唑啉酮类、磺酰脲类、草甘膦或草丁膦)的耐受性(例如“PAT”基因)。赋予所述所需性状的基因还可在转基因植物中以彼此结合的方式存在。转基因植物的实例包括重要的作物植物,例如谷类(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、糖用甜菜、甘蔗、番茄、豌豆和其他类型的蔬菜、棉花、烟草、油菜以及果实植物(具有下述果实: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。特别强调的性状是增强植物对昆虫、蛛形纲动物、线虫以及蛞蝓和蜗牛的抗性。
作物保护——处理的类型
利用式(I)的化合物来处理植物和植物部位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、生境或储存空间来进行,所述常规处理方法为例如浸渍、喷洒、喷雾、灌溉、蒸发、喷粉、雾化、撒播、发泡、喷涂、铺展、注射、浇水(浸透)、滴灌,以及在繁殖材料的情况下,尤其是在种子的情况下,还通过结壳、用一层或更多层涂料涂覆等方法作为粉末用于干种子处理、作为溶液用于液体种子处理、作为水溶性粉末用于浆剂处理。还可以通过超低量方法施用式(I)的化合物或者将式(I)化合物的使用形式或其本身注射到土壤中。
植物的一种优选的直接处理为叶面施用,即将式(I)的化合物施用到叶子上,其中处理频率和施用率应根据所述害虫的侵染水平来调节。
在系统性活性化合物的情况下,式(I)的化合物还通过根体系进入植物。然后,通过将式(I)的化合物作用于植物的生境来处理该植物。这可以通过下述方式来完成:例如浸透;或者混入土壤或营养液中,这意味着植物位点(例如土壤或水培系统)充满液体形式的式(I)的化合物;或土壤施用,这意味着将式(I)的化合物以固体形式(例如以颗粒的形式)引入到植物位点。在水稻作物的情况下,这还可以通过将式(I)的化合物以固体施用的形式(例如作为颗粒)计量加入淹没的稻田来完成。
种子处理
通过处理植物种子来防治动物害虫早已所知并且是不断改进的主题。然而,种子处理涉及一系列总是不能以令人满意的方式解决的问题。因此,需要开发保护种子和发芽作物的方法,所述方法不需要或至少显著降低在储存过程中、在播种后或植物出苗后农药的额外施用。还需要优化所使用的活性化合物的量,从而为种子和发芽植物提供最佳的保护以免于动物害虫的侵袭,而所使用的活性化合物不会损害植物本身。特别地,用于种子处理的方法还应考虑到害虫抗性或耐受性转基因植物的固有的杀昆虫和/或杀线虫特性,以便以作物保护产品的最少使用量获得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。根据本发明,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,其中在一个操作中或连续地用式(I)的化合物和混合组分同时处理种子。其还包括在不同的时间用式(I)的化合物和混合组分处理种子的方法。
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。在已在不同时间用式(I)的化合物和混合组分处理的种子的情况下,各物质可存在于种子的不同层中。在这种情况下,包含式(I)的化合物和混合组分的层可以任选地被中间层隔开。本发明还涉及这样的种子,其中已经施用作为部分包衣或作为除了包衣外的其他一层或其他多层的式(I)的化合物和混合组分。
本发明还涉及这样的种子,其在用式(I)的化合物处理后,经过薄膜包覆过程以避免该种子免受灰尘磨损。
用式(I)的化合物进行系统地作用的优势之一在于下列事实:通过处理种子,不仅保护种子本身还保护由其(出苗后)得到的植物免受动物害虫。以这种方式,可免除在播种时或在播种后不久对作物进行直接处理。
另一个优势在于,用式(I)的化合物处理种子可促进经处理的种子发芽和出苗。
同样认为有利的是,式(I)的化合物还可尤其用于转基因种子。
另外,式(I)的化合物还可与信号技术组合物或化合物结合使用,其使得共生体的集群(colonization)更好,例如根瘤菌、菌根和/或内生细菌或真菌,和/或优化固氮作用。
式(I)的化合物适用于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。更具体地,所述种子包括下列植物的种子: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、油菜、甜菜(例如糖用甜菜和饲用甜菜)、花生、蔬菜(例如西红柿、黄瓜、菜豆、十字花科蔬菜、洋葱和生菜)、果实植物、草坪植物和观赏性植物。特别重要的是处理谷物(小麦、大麦、黑麦、燕麦)、玉米、大豆、棉花、加拿大油菜、油菜和稻的种子。
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。所述种子包括通常包含至少一种防治特别是具有杀昆虫和/或杀线虫特性的多肽的表达的异源基因的植物的种子。转基因种子中的异源基因可来自微生物如芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单孢菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棒形杆菌属(Clavibacter)、球囊霉属(Glomus)或粘帚霉属(Gliocladium)。本发明特别适合于处理包含至少一种源自芽孢杆菌属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(Bacillus thuringiensis)。
在本发明的上下文中,将式(I)的化合物施用于种子。优选在这样的状态下处理种子:其足够稳定以使得在处理过程中不发生损害。一般而言,种子可在采收和播种之间的任意时间处理。通常使用已从植物分离并且已除去穗轴、外壳、茎、表皮、毛或果肉的种子。例如,可使用已采收、清洁并干燥至允许贮存的水分含量的种子。或者,也可使用在干燥之后例如再经水处理,然后再经干燥(例如灌注)的种子。
在处理种子时,通常必须确保以这样的方式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,使得种子的发芽不会受到不利的影响以及所得植物不会受到损害。在某些施用率下,在可表现出毒害植物效应的活性化合物的情况下,这必须特别保证。
通常,式(I)的化合物以合适的制剂形式施用于种子。合适的制剂和种子处理方法是本领域技术人员已知的。
可将式(I)的化合物转化为常规拌种制剂,例如溶液剂、乳剂、悬液剂、粉剂、泡沫剂、浆剂或用于种子的其他包衣组合物,以及ULV制剂。
这些制剂以已知的方式通过将式(I)的化合物与常规添加剂混合而制备,所述添加剂为例如常规的增量剂以及溶剂或稀释剂、着色剂、湿润剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、粘合剂、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所述目的的所有染料。可以使用微溶于水的颜料,或者可溶于水的染料。实例包括已知的命名为罗丹明B(Rhodamine 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且通常用于活性农用化学化合物制剂的所有物质。优选使用萘磺酸烷基酯,例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/或乳化剂为通常用于活性农用化学化合物制剂中的所有非离子、阴离子和阳离子分散剂。优选使用非离子或阴离子分散剂或者非离子或阴离子分散剂的混合物。合适的非离子分散剂特别包括环氧乙烷/环氧丙烷嵌段共聚物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚、以及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其是木素磺酸盐、聚丙烯酸盐、以及芳基磺酸盐/甲醛的缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为通常用于活性农用化学化合物制剂中的所有泡沫抑制物质。优选使用硅酮消泡剂和硬脂酸镁。
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。实例包括二氯苯和苯甲醇半缩甲醛。
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、改性粘土和细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的粘和剂为可在拌种产品中使用的所有常规粘结剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和纤基乙酸钠(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.Wegle,“Chemie derPflanzenschutz-und ”,[Chemistry of the CropProtection Compositions and Pesticides],第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可以直接或预先用水稀释后用于处理多种不同种类的种子。例如,可使用浓缩剂或通过用水稀释而由其得到的制剂来拌种下列种子: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,或多种不同的蔬菜种子。根据本发明使用的拌种制剂或其稀释使用形式还可用于拌种转基因植物的种子。
对于用根据本发明使用的拌种制剂或通过添加水而由其制备的使用形式来处理种子而言,常规用于拌种的所有混合单元均为可用的。更具体地,拌种的过程为:将种子分批或连续地置于混合器中;以其本身或预先用水稀释之后,加入特定所需量的拌种制剂;并进行混合直到制剂均匀分布于种子上。如果合适的话,随后进行干燥操作。
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。其取决于该制剂中式(I)的化合物的具体含量以及种子。式(I)的化合物的施用率通常为每千克种子0.001g至50g,优选每千克种子0.01g至15g。
动物健康
在动物健康领域中,即在兽医学领域中,式(I)的化合物对动物寄生虫、特别是外寄生虫或内寄生虫有活性。术语“内寄生虫”特别包括蠕虫纲和原生动物,例如球虫目。外寄生虫通常且优选为节肢动物,尤其为昆虫和螨。
在兽医学领域中,具有有利的恒温动物毒性的式(I)的化合物适用于防治在动物繁育和动物畜牧中遇到的在家畜、繁育动物、动物园动物、实验室动物、实验动物和驯养动物上的寄生虫。它们对寄生虫发育的所有阶段或特定阶段有活性。
农业家畜包括,例如,哺乳动物,例如,绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿且尤其是牛和猪;家禽,例如,火鸡、鸭、鹅且尤其是鸡;例如在水产养殖中的鱼和甲壳动物;以及昆虫,例如蜜蜂。
驯养动物包括,例如,哺乳动物,例如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,尤其是狗、猫;笼鸟;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)的化合物施用于哺乳动物。
在另一个优选的实施方案中,将式(I)的化合物施用于禽类,即笼鸟,尤其是家禽。
式(I)的化合物用于防治动物寄生虫的用途旨在减少或预防疾病、死亡病例及性能下降(在肉、奶、毛、皮、蛋、蜜等的情况下),以使得更经济的和更简单的动物饲养成为可能,并可实现更好的动物健康。
关于动物健康的领域,术语“防治(control)”或“防治(controlling)”意指,式(I)的化合物有效地将被特定寄生虫感染的动物中的所述寄生虫的发生率降低至无害水平。更具体地,本文中的“防治”意指,式(I)的化合物可杀死相应的寄生虫、抑制它的生长或抑制它的增殖。
节肢动物包括:
虱目(Anoplurida),例如血虱属种(Haematopinus spp.)、毛虱属种(Linognathusspp.)、虱属种(Pediculus spp.)、阴虱属种(Phtirus spp.)、盲虱属种(Solenopotesspp.);食毛目(Mallophagida)以及钝角亚目(Amblycerina)和丝角亚目(Ischnocerina),例如毛羽虱属种(Trimenopon spp.)、禽虱属种(Menopon spp.)、巨羽虱属种(Trinotonspp.)、牛羽虱属种(Bovicola spp.)、Werneckiella属种、Lepikentron属种、畜虱属种(Damalina spp.)、嚼虱属种(Trichodectes spp.)、猫羽虱属种(Felicola spp.);双翅目(Diptera)以及长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属种(Aedes spp.)、按蚊属种(Anopheles spp.)、库蚊属种(Culex spp.)、蚋属种(Simuliumspp.)、真蚋属种(Eusimulium spp.)、白蛉属种(Phlebotomus spp.)、罗蛉属种(Lutzomyiaspp.)、库蠓属种(Culicoides spp.)、斑虻属种(Chrysops spp.)、短蚋属种(Odagmiaspp.)、维蚋属种(Wilhelmia spp.)、瘤虻属种(Hybomitra spp.)、黄虻属种(Atylotusspp.)、虻属种(Tabanus spp.)、麻虻属种(Haematopota spp.)、Philipomyia属种、蜂虱蝇属种(Braula spp.)、家蝇属种(Musca spp.)、齿股蝇属种(Hydrotaea spp.)、螫蝇属种(Stomoxys spp.)、黑角蝇属种(Haematobia spp.)、莫蝇属种(Morellia spp.)、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.)、狂蝇属种(Oestrus spp.)、皮蝇属种(Hypoderma spp.)、胃蝇属种(Gasterophilus spp.)、虱蝇属种(Hippobosca spp.)、羊虱蝇属种(Lipoptena spp.)、蜱蝇属种(Melophagus spp.)、鼻狂蝇属种(Rhinoestrus spp.)、大蚊属种(Tipula spp.);蚤目(Siphonapterida),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),例如臭虫属种(Cimex spp.)、锥猎蝽属种(Triatomaspp.)、红猎蝽属种(Rhodnius spp.)、锥蝽属种(Panstrongylus spp.);以及来自蜚蠊目(Blattarida)的公害和卫生害虫。
节肢动物还包括:
蜱螨亚纲(Acari)(螨蜱目(Acarina))和后气门目(Metastigmata),例如软蜱科(argasidae),如锐缘蜱属种(Argas spp.)、钝缘蜱属种(Ornithodorus spp.)、残喙蜱属种(Otobius spp.);硬蜱科(Ixodidae),如硬蜱属种(Ixodes spp.)、花蜱属种(Amblyommaspp.)、扇头蜱属种(牛蜱属种)(Rhipicephalus(Boophilus)spp.)、革蜱属种(Dermacentorspp.)、血蜱属种(Haemophysalis spp.)、璃眼蜱属种(Hyalomma spp.)、扇头蜱属种(Rhipicephalus spp.)(多宿主蜱的原属);中气门目(Mesostigmata),如皮刺螨属种(Dermanyssus spp.)、禽刺螨属种(Ornithonyssus spp.)、肺刺螨属种(Pneumonyssusspp.)、刺利螨属种(Raillietia spp.)、肺刺螨属种(Pneumonyssus spp.)、胸刺螨属种(Sternostoma spp.)、蜂螨属种(Varroa spp.)、蜂盾螨属种(Acarapis spp.);辐螨目(Actinedida)(前气门目(Prostigmata)),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(Trombiculaspp.)、Neotrombiculla属种、Listrophorus属种;以及粉螨目(Acaridida)(无气门亚目(Astigmata)),例如粉螨属种(Acarus spp.)、食酪螨属种(Tyrophagus spp.)、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.)、皮螨属种(Chorioptes spp.)、耳疥螨属种(Otodectes spp.)、疥螨属种(Sarcoptes spp.)、耳螨属种(Notoedres spp.)、鸟疥螨属种(Knemidocoptesspp.)、气囊螨属种(Cytodites spp.)、鸡雏螨属种(Laminosioptes spp.)。
寄生的原生动物包括:
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(根足总纲)(Sarcomastigophora(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(孢子纲)(Apicomplexa(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)、球虫属(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(I.spec.)、猪等孢子虫(I.suis)、Cystisospora spec.、隐孢子虫属(Cryptosporidiumspec.),特别是C.parvum;例如弓形虫科(Toxoplasmadidae),例如鼠弓形虫(Toxoplasmagondii)、Hammondia heydornii、Neospora caninum、贝斯虫(Besnoitia besnoitii);例如肉孢子虫科(Sarcocystidae),例如牛犬肉孢子虫(Sarcocystis bovicanis)、牛人肉孢子虫(S.bovihominis)、羊犬肉孢子虫(S.ovicanis)、羊猫肉孢子虫(S.ovifelis)、S.neurona、肉孢子虫属(S.spec.)、猪人肉孢子虫(S.suihominis),例如Leucozoidae,例如Leucozytozoon simondi,例如症原虫科(Plasmodiidae),例如,伯氏鼠症原虫(Plasmodiumberghei)、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(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(B.spec.)、泰勒原虫(Theileria parva),泰勒虫属(Theileria spec.),例如匿虫亚目(Adeleina),例如,犬肝簇虫(Hepatozoon canis)、肝簇虫属(H.spec.);
蠕虫纲(helminths)的病原性内寄生虫,包括扁形动物(例如单殖亚纲(monogenea)、绦虫(cestodes)和吸虫(trematodes))、线虫、棘头纲(acanthocephala)及舌形虫属种(pentastoma)。这些包括:
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:假叶目(Pseudophyllidea),例如:裂头绦虫属种(Diphyllobothriumspp.)、迭宫绦虫属种(Spirometra spp.)、Schistocephalus属种、舌状绦虫属种(Ligulaspp.)、吸叶绦虫属种(Bothridium spp.)、大复殖孔绦虫属种(Diplogonoporus spp.);
圆叶目(Cyclophyllidea),例如:中殖孔绦虫属种(Mesocestoides spp.)、裸头绦虫属种(Anoplocephala spp.)、Paranoplocehala属种、蒙尼绦虫属种(Moniezia spp.)、Thysanosomsa属种、曲子宫绦虫属种(Thysaniezia spp.)、无卵黄腺绦虫属种(Avitellinaspp.)、西里西亚绦虫属种(Stilesia spp.)、鸣绦虫属种(Cittotaenia spp.)、Andyra属种、伯特绦虫属种(Bertiella spp.)、血寄生绦虫属种(Taenia spp.)、棘球绦虫属种(Echinococcus spp.)、泡尾绦虫属种(Hydatigera spp.)、代凡绦虫属种(Davaineaspp.)、方形绦虫属种(Raillietina spp.)、膜壳绦虫属种(Hymenolepis spp.)、棘鳞绦虫属种(Echinolepis spp.)、棘叶绦虫属种(Echinocotyle spp.)、双睾绦虫属种(Diorchisspp.)、犬复孔绦虫属种(Dipylidium spp.)、约优克斯绦虫属种(Joyeuxiella spp.)、复孔绦虫属种(Diplopylidium spp.);
吸虫:复殖纲(Digenea),例如:双穴吸虫属种(Diplostomum spp.)、茎穴吸虫属种(Posthodiplostomum spp.)、血吸虫属种(Schistosoma spp.)、毛血吸虫属种(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.)、短咽类吸虫属种(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.)、片形吸虫属种(Fasciolides spp.)、姜片虫属种(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.)、Gigantoctyle属种、菲策吸虫属种(Fischoederius spp.)、Gastrothylacus属种、背孔吸虫属种(Notocotylus spp.)、下弯吸虫属种(Catatropisspp.)、斜睾吸虫属种(Plagiorchis spp.)、前殖吸虫属种(Prosthogonimus spp.)、双腔吸虫属种(Dicrocoelium spp.)、阔盘吸虫属种(Eurytema spp.)、隐孔吸虫属种(Troglotrema spp.)、并殖吸虫属种(Paragonimus spp.)、豆形肛瘤吸虫属种(Collyriclum spp.)、侏形吸虫属种(Nanophyetus spp.)、后睾吸虫属种(Opisthorchisspp.)、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(Metagonimus spp.);
线虫:Trichinellida,例如:鞭虫属种(Trichuris spp.)、毛细线虫属种(Capillaria spp.)、Paracapillaria属种、真鞘线虫属种(Eucoleus spp.)、Trichomosoides属种、旋毛形线虫属种(Trichinella spp.);
垫刃目(Tylenchida),例如:Micronema属种、类圆线虫属种(Strongyloidesspp.);
小杆目(Rhabditina),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.)、辐首属种(Gyalocephalus spp.)、柱咽属种(Cylindropharynx spp.)、盂口属种(Poteriostomum spp.)、Cyclococercus属种、Cylicostephanus属种、结节线虫属种(Oesophagostomum spp.)、夏氏线虫属种(Chabertia spp.)、冠线虫属种(Stephanurusspp.)、钩口线虫属种(Ancylostoma spp.)、钩虫属种(Uncinaria spp.)、仰口线虫属种(Bunostomum spp.)、球首属种(Globocephalus spp.)、比翼线虫属种(Syngamus spp.)、Cyathostoma属种、后圆线虫属种(Metastrongylus spp.)、网尾线虫属种(Dictyocaulusspp.)、缪勒线虫属种(Muellerius spp.)、原圆线虫属种(Protostrongylus spp.)、Neostrongylus属种、囊尾线虫属种(Cystocaulus spp.)、Pneumostrongylus属种、Spicocaulus属种、Elaphostrongylus属种、副鹿圆线虫属种(Parelaphostrongylusspp.)、环体线虫属种(Crenosoma spp.)、Paracrenosoma属种、奥斯勒线虫属种(Oslerusspp.)、血管圆线虫属种(Angiostrongylus spp.)、猫圆线虫属种(Aelurostrongylusspp.)、类丝虫属种(Filaroides spp.)、副类线虫属种(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(Teladorsagia spp.)、马歇尔线虫属种(Marshallagiaspp.)、短古柏线虫属种(Cooperia spp.)、细颈线虫属种(Nematodirus spp.)、猪圆线虫属种(Hyostrongylus spp.)、Obeliscoides属种、裂口线虫属种(Amidostomum spp.)、盘头线虫属种(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.)、三种管状属种(Syphacia spp.)、无刺线虫属种(Aspiculuris spp.)、异刺属种(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(Baylisascarisspp.)、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(Physalopteraspp.)、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(Draschiaspp.)、龙线虫属种(Dracunculus spp.);冠丝虫属种(Stephanofilaria spp.)、副丝虫属种(Parafilaria spp.)、鬃丝虫属种(Setaria spp.)、罗阿丝虫属种(Loa spp.)、恶丝虫属种(Dirofilaria spp.)、类平滑丝虫属种(Litomosoides spp.)、布鲁格丝虫属种(Brugiaspp.)、吴策线虫属种(Wuchereria spp.)、盘尾属种(Onchocerca spp.)、旋尾线虫属种(Spirocerca spp.);
棘头虫纲(Acanthocephala):少棘目(Oligacanthorhynchida),例如:巨吻棘虫属种(Macracanthorhynchus spp.)、前睾棘头虫属种(Prosthenorchis spp.);多态目(Polymorphida),例如:细颈棘头虫属种(Filicollis spp.);念珠菌目(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.);
舌形虫属(Pentastoma):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)的化合物以合适制剂的形式通过本领域中通常已知的方法(例如肠内、肠胃外、皮肤或鼻途径)给药。给药可以是预防性的或治疗性的。
因此,本发明的一个实施方案涉及式(I)的化合物用作药物的用途。
另一个方面涉及式(I)的化合物用作抗内寄生虫剂、尤其是杀蠕虫剂或抗原生动物剂的用途。式(I)的化合物适于例如在动物畜牧业中、在动物繁育中、在动物圈养中及在卫生领域中用作抗内寄生虫剂、尤其是杀蠕虫剂或抗原生动物剂。
另一个方面还涉及式(I)的化合物用作抗外寄生虫剂、尤其是杀节肢动物剂(例如,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畜牧业中、在动物繁育中、在动物圈养中或在卫生领域中用作抗外寄生虫剂,尤其是杀节肢动物剂(例如,杀昆虫剂或杀螨剂)的用途。
抗蠕虫混合组分
例如可提及下列抗蠕虫混合组分:
包括杀线虫和杀绦虫活性化合物的抗蠕虫活性化合物:
大环内酯类,例如,阿维菌素(abamectin)、多拉菌素(doramectin)、甲氨基阿维菌素(emamectin)、依立诺克丁(eprinomectin)、伊佛霉素(ivermectin)、米尔倍霉素(milbemycin)、莫西菌素(moxidectin)、尼莫克汀(nemadectin)、塞拉菌素(selamectin);
苯并咪唑类和聚苯并咪唑类(probenzimidazoles),例如,阿苯达唑(albendazole)、阿苯达唑亚砜(albendazole-sulphoxide)、坎苯达唑(cambendazole)、环苯达唑(cyclobendazole)、非班太(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)、丁苯咪酯(parbendazole)、噻苯达唑(thiabendazole)、托布津(thiophanate)、三氯苯达唑(triclabendazole);
环辛缩肽(cyclooctadepsipeptides)类,例如,emodepside、PF 1022;
氨基乙腈衍生物类,例如,monepantel;
四氢嘧啶类,例如:甲噻嘧啶(morantel)、噻嘧啶(pyrantel)、奥克太尔(oxantel);
咪唑并噻唑类(Imidazothiazoles),例如,丁咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
水杨酰苯胺(salicylanilides)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)、三溴水杨酰苯胺(tribromsalan);
paraherquamides类,例如得曲恩特(derquantel)、paraherquamide;
氨基苯基脒类,例如:阿米登太(amidantel)、脱酰基的阿米登太(dAMD)、三苯双脒;
有机磷酸酯类,例如,蝇毒磷(coumaphos)、育畜磷(crufomate)、敌敌畏(dichlorvos)、哈洛克酮(haloxone)、驱虫磷(naphthalofos)、敌百虫(trichlorfon);
取代的苯酚类,例如,硫氯酚(bithionol)、二碘硝酚(disophenol)、六氯酚(hexachlorophene)、硝氯酚(niclofolan)、联硝氯酚(meniclopholan)、硝碘酚腈(nitroxynil);
哌嗪酮,例如:吡喹酮(praziquantel)、依西太尔(epsiprantel);
不同的其它种类,例如,硝硫氰胺(amoscanate)、酚乙铵(bephenium)、丁萘脒(bunamidine)、氯硝安定(clonazepam)、氯舒隆(clorsulon)、联胺苯醚(diamfenetid)、双氯酚(dichlorophen)、乙胺嗪(diethylcarbamazine)、吐根碱(emetine)、三氯苯丙酰嗪(hetolin)、海恩酮(hycanthone)、硫蒽酮(lucanthone)、盐酸卢甘宋(Miracil)、mirasan、氯硝柳胺(niclosamide)、硝唑咪(niridazole)、硝碘酚腈(nitroxynil)、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)。
载体防治
式(I)的化合物还可用于载体防治。在本发明的上下文中,载体为能将病原体(例如病毒、蠕虫、单细胞生物和细菌)从贮主(植物、动物、人等)传播给宿主的节肢动物,尤其是昆虫或蛛形纲动物。病原体可被机械地传播给宿主(例如通过无刺蝇(non-stinging)的沙眼),或者可在注射后传播给宿主(例如通过蚊子的疟原虫)。
载体以及它们传播的疾病或病原体的实例为:
1)蚊
-按蚊属:疟疾、丝虫病;
-库蚊属:日本脑炎、丝虫病、其他病毒性疾病、蠕虫的传播;
-伊蚊属: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(epidemic typhus);
3)跳蚤:鼠疫、地方性斑疹伤寒;
4)蝇类:昏睡病(锥体虫病(trypanosomiasis))、霍乱、其他细菌性疾病;
5)螨:壁虱病、流行性斑疹伤寒、立克次氏体痘、土拉菌病、圣路易斯脑炎(SaintLouis encephalitis)、蜱媒脑炎(tick-borne encephalitis)(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、疏螺旋体病(borreliosis);
6)蜱:疏螺旋体病(borellioses)如达氏疏螺旋体(Borrelia duttoni)、蜱媒脑炎、Q热(贝氏柯克斯体(Coxiella burnetii))、焦虫病(babesioses)(犬巴贝斯虫(Babesiacanis canis))。
在本发明的上下文中,载体的实例为昆虫,例如蚜虫、蝇、叶蝉或蓟马(thrip),其可向植物传播植物病毒。能够传播植物病毒的其他载体为蛛状螨、虱、甲虫和线虫。
在本发明的上下文中,载体的其他实例为昆虫和蛛形纲动物,例如蚊,尤其是伊蚊属、按蚊属的蚊,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);以及库蚊属蚊子、虱、跳骚、蝇、螨和蜱,其可向动物和/或人类传播病原体。
如果式(I)的化合物为抗破坏性的,则载体防治也是可行的。
式(I)的化合物适合用于预防通过载体传播的疾病和/或病原体。因此,本发明的另一个方面为式(I)的化合物在例如农业、园艺、林业、园林以及休闲设备中,以及材料和贮存产品的保护中用于载体防治的用途。
工业材料的保护
式(I)的化合物适合用于保护工业材料免受昆虫的侵袭或破环,例如来自鞘翅目、膜翅目、等翅目、鳞翅目、啮虫目和衣鱼目(Zygentoma)的昆虫。
在本文中,工业材料应理解为意指无生命材料,例如,优选塑料、粘合剂、胶料、纸和纸片、皮革、木材、加工的木制品和涂层组合物。特别优选本发明的用于保护木材的用途。
在另一个实施方案中,式(I)的化合物连同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)的化合物表现为即用型(ready-to-use)农药,即它们不需要其他修饰即可应用到所述材料上。合适的其他杀昆虫剂或杀真菌剂特别为上述提及的那些。
出乎意料地,还已经发现,式(I)的化合物可用于保护与盐水或微咸水接触的物体(尤其是船体、筛、网、建筑物、系船设备及信号系统)免受污染。式(I)的化合物同样可单独或与其他活性化合物结合用作防污剂。
卫生领域中动物害虫的防治
式(I)的化合物适合用于防治卫生领域中的动物害虫。更具体而言,本发明可以用于家用领域、卫生领域和储存产品的保护中,特别是用于防治密闭空间中遭遇的昆虫、蛛形纲动物和螨,所述密闭空间为例如住所、工厂车间、办公室、车辆客舱。为了防治动物害虫,式(I)的化合物单独或与其他活性化合物和/或助剂结合使用。它们优选用于家用的杀昆虫剂产品中。式(I)的化合物对敏感的及抗性物种以及对全部发育阶段均有效。
这些害虫包括,例如,来自下述的害虫:蛛形纲;蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足纲和倍足纲;昆虫纲的蜚蠊目;鞘翅目、革翅目、双翅目、异翅亚目、膜翅目、等翅目、鳞翅目、虱目(Phthiraptera)、啮虫目、跳跃目(Saltatoria)或直翅目、蚤目和衣鱼目;软甲亚纲的等足目。
在用于扩展的诱饵或诱饵站(bait station)中,施用以下列形式进行: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、烟雾剂、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(energy-free)或无源(passive)的蒸发体系、捕蛾纸、捕蛾袋和捕蛾胶;作为颗粒剂或粉剂。
实施例:
方法和中间体的说明
以下制备和用途实施例阐明本发明而不限制本发明。所述产物通过1H-NMR光谱和/或LC-MS(液相色谱质谱联用光谱法)和/或GC-MS(气相色谱质谱联用光谱法)进行表征。
logP值以类似于OECD Guideline 117(EC directive 92/69/EEC)的方式通过使用反相柱(C18)的HPLC(高效液相色谱)测定,所述测定使用以下方法:
[a]酸性范围中的LC-MS测定用0.1%甲酸水溶液和乙腈(含0.1%甲酸)作为洗脱剂在pH 2.7下进行,线性梯度为10%乙腈至95%乙腈。logP[a]还称为logP(HCOOH)。
[b]中性范围中的LC-MS测定用0.001摩尔的碳酸氢铵水溶液和乙腈作为洗脱剂在pH 7.8下进行;线性梯度为10%乙腈至95%乙腈。logP[b]还称为logP(中性)。
使用同系列的具有已知logP值(通过在两个连续的烷酮之间的线性插值法基于保留时间所测定的logP值)的无支链烷-2-酮(其具有3至16个碳原子)溶液进行校准。
用安装有1.7mm TCI探头的Bruker II Avance 400测定NMR谱。在个别情况下,使用Bruker Avance II 600测定NMR谱。
所选择的实施例的NMR数据以常规形式列出(δ值,多重态分裂,氢原子的数目)。信号的分裂描述如下:s(单峰),d(二重峰),t(三重峰),q(四重峰),m(多重峰),broad(宽信号)。所用溶剂为CD3CN、CDCl3或D6-DMSO,并使用四甲基硅烷(0.00ppm)作为参比。
GC-MS光谱利用50℃至320℃的温度梯度使用Agilent 6890GC,HP 5973 MSD在二甲基硅酮相中进行测定。GC-MS指数作为Kovats指数使用同系列的正烷烃(具有8至38的偶数个碳原子)溶液进行测定。
制备实施例1:3-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-6-(三氟甲基)嘧啶-4(3H)-酮(实施例编号2)
步骤1:4,4,4-三氟-N-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫烷基]苯基}-3-羟基丁-2-烯酰胺(实施例编号XXXI-1)
首先,将2g(8.36mmol)的2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫烷基]苯胺加入到42ml的甲苯中。加入2.48ml(16.7mmol)的4,4,4-三氟乙酰乙酸乙酯和20.4mg(0.16mmol)的4-DMAP,并将反应混合物加热回流14h。反应混合物冷却后,在旋转蒸发仪上减压除去溶剂,无需进一步纯化将残留物(3.45g)转移到步骤2中。
logP(HCOOH):2.77
步骤2:3-氨基-4,4,4-三氟-N-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫烷基]苯基}丁-2-烯酰胺(实施例编号IIa-1)
将残留物(3.45g)溶解于乙酸乙酯(37.5ml)中,并加入乙酸铵(4.51g,58.5mmol)。将反应混合物加热回流7h。反应混合物冷却后,加入乙酸乙酯(64ml),并将有机相先用水洗涤,再用饱和NaCl溶液洗涤。将有机相用MgSO4干燥,并将溶剂在旋转蒸发仪上减压移出。无需纯化将残留物(2.78g)转移到步骤3中。
logP(HCOOH):3.61
步骤3:3-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫烷基]苯基}-6-(三氟甲基)嘧啶-4(3H)-酮(实施例编号1)
将残留物(2.78g)溶于DMF-DMA(6.2g)中,并在100℃下搅拌7h。反应混合物冷却后,将溶剂在旋转蒸发仪上减压移出,并将残留物溶于甲酸(17ml)中,将反应混合物加热回流2h。反应混合物冷却后,将溶剂在旋转蒸发仪上减压移出,并将乙酸乙酯加入至残留物中。将有机相用水洗涤,并用MgSO4干燥。将溶剂在旋转蒸发仪上减压移出,并将残留物用MPLC(环己烷/丙酮)纯化。得到670mg的标题化合物(经过3个步骤的理论值的27%,根据LC-MS测得纯度为80%)。通过MPLC(环己烷/乙酸乙酯)进一步纯化得到157mg的具有更高纯度的标题化合物(根据LC-MS的100%)。
1H-NMR(D6-DMSO)δppm:8.72(s,1H),7.89(d,1H),7.48(d,1H),7.17(s,1H),4.01(q,2H),2.44(s,3H)
logP(HCOOH):3.42 logP(中性):3.4
步骤4:3-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-6-(三氟甲基)嘧啶-4(3H)-酮(实施例编号2)
首先,将190mg(0.492mmol)的3-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫烷基]苯基}-6-(三氟甲基)嘧啶-4(3H)-酮加入到二氯甲烷中,加入124mg(0.541mmol)的间氯过苯甲酸,并将反应混合物在0℃搅拌3h,然后用硫代硫酸钠和碳酸氢钠溶液萃取。将有机相用硫酸镁干燥,并过滤。在减压下移出溶剂得到170mg的标题化合物(理论值的84%,根据LC/MS的纯度为97%)。
1H-NMR(D6-DMSO)δppm:8.75(s,1H),8.17(d,1H),7.59(d,1H),7.17(s,1H),4.29-4.22(m,1H),4.07-4.01(m,1H),2.48(s,3H)
logP(HCOOH):2.4 logP(中性):2.38
制备实施例2:3-[2,4-二甲基-5-(2,2,2-三氟乙基亚磺酰基)苯基]-6-(三氟甲基)嘧啶-4-酮(实施例编号6)
步骤1:N-[2,4-二甲基-5-(2,2,2-三氟乙基硫烷基)苯基]-4,4,4-三氟-3-羟基丁-2-烯酰胺(实施例编号XXXI-2)
首先,将5g(21.2mmol)的2,4-二甲基-5-[(2,2,2-三氟乙基)硫烷基]苯胺加入到42ml的甲苯中。加入6.21ml(42.5mmol)的4,4,4-三氟乙酰乙酸乙酯和51.9mg(0.42mmol)的4-DMAP,并将反应混合物加热回流14h。反应混合物冷却后,将溶剂在旋转蒸发仪上减压移出,无需进一步纯化将残留物(7.93g)转移到步骤2中。
logP(HCOOH):2.87
步骤2:3-氨基-N-[2,4-二甲基-5-(2,2,2-三氟乙基硫烷基)苯基]-4,4,4-三氟丁-2-烯酰胺(实施例编号IIA-2)
将残留物(7.93g)溶于乙酸乙酯(82.8ml)中,并加入乙酸铵(6.68g,86.6mmol)。将反应混合物加热回流7h。反应混合物冷却后,将溶剂在旋转蒸发仪上减压移出。无需进一步纯化将残留物(7.91g)转移到步骤3中。
logP(HCOOH):3.63
步骤3:3-[2,4-二甲基-5-(2,2,2-三氟乙基硫烷基)苯基]-6-(三氟甲基)嘧啶-4-酮(实施例编号5)
将残留物(7.91g)溶于原甲酸三乙酯(53ml)中,并加入硫酸(0.33ml)。将混合物在140℃下搅拌3h。反应混合物冷却后,将溶剂在旋转蒸发仪上减压移出。将水加入到残留物中,并用乙酸乙酯萃取混合物。将有机相用Na2SO4干燥,并过滤。将溶剂在旋转蒸发仪上减压移出,并用MPLC(环己烷/丙酮)纯化残留物。得到2.99g的标题化合物(经过3个步骤的理论值的37%,根据LC-MS测得纯度为96%)。
1H-NMR(D6-DMSO)δppm:8.59(s,1H),7.64(s,1H),7.33(s,1H),7.13(s,1H),4.00(q,2H),2.38(s,3H),2.04(s,3H)
logP(HCOOH):3.56 logP(中性):3.5
步骤4:3-[2,4-二甲基-5-(2,2,2-三氟乙基亚磺酰基)苯基]-6-(三氟甲基)嘧啶-4-酮(实施例编号6)
首先,将500mg(1.30mmol)的3-[2,4-二甲基-5-(2,2,2-三氟乙基硫烷基)苯基]-6-(三氟甲基)嘧啶-4-酮加入到二氯甲烷(25ml)中,加入331mg(1.43mmol)的间氯过苯甲酸,并将反应混合物在0℃搅拌1h,然后用硫代硫酸钠和碳酸氢钠溶液洗涤。将有机相用硫酸钠干燥,并过滤。在减压下移出溶剂得到490mg的标题化合物(理论值92%,根据LC/MS测得纯度为98%)。
1H-NMR(D6-DMSO)δppm:8.64-8.62(m,1H),7.92(s,1H),7.47-7.44(m,1H),7.13(s,1H),4.30-3.88(m,2H),2.43(s,3H),2.15(s,3H)
logP(HCOOH):2.43 logP(中性):2.39
通过HPLC在手性柱(ChiralCel OJ-H,例如5nm 250×4.6mm)上使用流动相庚烷/甲醇/乙醇由外消旋体通过将其制备性地分离来获得对映体。
在Perkin Elmer 341,序号9123上于589nm的波长和20℃的温度下测定旋光度。
下列的比旋光度(specific optical rotation)应理解为5种不同的测量值的平均值:
对映体1(实施例编号56):在CHCl3中为89.5(c=0.022)
对映体2(实施例编号49):在CHCl3中为-87.8(c=0.019)
通过上述方法,制备下列式(I)的化合物。
表1:具有结构(I-A)的式(I)的化合物
其中W=F和V=O
另外,根据上述方法制备下列式(IIa)的化合物(参见表2)和式(XXXI)的化合物(参见表3)。
表2:式(IIa)的化合物
其中W=F
n.d.=未测定
表3:式(XXXI)的化合物
其中W=F
n.d.=未测定
NMR峰列表的方法
所选实施例的1H NMR数据以1H NMR峰列表的形式记录。对于每个信号峰,首先列出以ppm计的δ值,然后列出圆括号内的信号强度。对于不同信号峰的δ值-信号强度数对之间彼此以分号分隔列出。
因此,一个实施例的峰列表采用以下形式:
δ1(强度1);δ2(强度2);........;δi(强度i);........;δn(强度n)
尖峰信号的强度与NMR光谱的输出实例中的信号高度(以cm计)相关,并且示出了信号强度的真实比例。对于宽峰信号,可以示出信号的若干峰值或中值,以及其与光谱中的最强信号相比的相对强度。
对于1H NMR光谱的化学位移的校准,我们使用四甲基硅烷和/或溶剂的化学位移,特别是对于在DMSO中测量的光谱而言。因此,四甲基硅烷峰可以但不一定在NMR峰列表中出现。
1H NMR峰的列表类似于常规1H NMR的打印输出,并因此通常包括在常规NMR解析中列出的所有峰。
另外,如同常规1H NMR的打印输出,其可显示溶剂信号、目标化合物的立体异构体(其同样构成了本发明的部分主题)的信号、和/或杂质峰的信号。
在溶剂和/或水的δ范围内的化合物信号的记录中,我们的1H NMR峰的列表显示出常见的溶剂峰,例如在DMSO-D6中的DMSO峰以及水峰,这通常平均具有高强度。
目标化合物的立体异构体的峰和/或杂质的峰通常具有比所述目标化合物(例如具有>90%的纯度)的峰平均更低的强度。
这些立体异构体和/或杂质对于特定的制备方法而言可能是典型的。因此,在这种情况下,它们的峰可参照“副产物指纹”而有助于识别我们的制备方法的再现性。
专业人员通过已知方法(MestreC,ACD模拟,且使用经验评估的预期值)计算目标化合物的峰,并且可以根据需要,任选地使用其他强度滤波器离析出目标化合物的峰。这种离析类似于常规1H NMR解析中的相关峰的挑选。
1H NMR峰列表的其他细节可参见研究公开数据库第564025号(ResearchDisclosure Database Number 564025)。
表4:表1的化合物的NMR数据:
用途实施例:
1.微小牛蜱(Boophilus microplus)-注射测试
溶剂:二甲亚砜
为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,并将浓液用溶剂稀释到所需浓度。
将1μl活性化合物溶液注射到5只过饱的成年雌牛蜱(微小牛蜱)的腹部。将该动物转移到培养皿中,并保持在温控室中。
7天后,通过受精卵的产卵数来评估功效。将没有明显能育性的卵储存在温控箱中,直到约42天后幼虫孵化出来。100%的功效意指没有牛蜱产下任何受精卵;0%意指所有卵都是能育性的。
在该测试中,例如,由制备实施例获得的下列化合物在20μg/动物的施用率下显示出100%的功效:2、4、5、6、9、22、26、34、47、50、53、59。
2.根结线虫(Meloidogyne incognita)测试
溶剂:125.0重量份的丙酮
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂混合,并将浓液用水稀释至所需浓度。
在容器内装入沙子、活性化合物溶液、南方根结线虫(根结线虫)的卵/幼虫的悬浮液和莴笋种子。莴笋种子发芽,并长成植物。虫瘿在根部发育。
14天后,通过形成的虫瘿测定以%计的杀线虫功效。100%意指未发现虫瘿;0%意指经处理的植物上的虫瘿数量相当于未经处理的对照组。
在该测试中,例如,由制备实施例获得的下列化合物在20ppm的施用率下显示出100%的功效:18、21、33、45、55。
在该测试中,例如,由制备实施例获得的下列化合物在20ppm的施用率下显示出90%的功效:9、12、18、21、26、27、30、41、55。
3.辣根猿叶甲(Phaedon cochleariae)-喷雾测试
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
为制备合适的活性化合物制剂,使用规定重量份的溶剂来溶解1重量份的活性化合物,并用含有浓度为1000ppm的乳化剂的水调节直至获得所需浓度。为制备其他测试浓度,用含有乳化剂的水稀释所述制剂。
在大白菜叶片的叶面上喷洒所需浓度的活性化合物制剂,并在干燥后,接种芥菜甲虫(辣根猿叶甲)的幼虫。
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。
在该测试中,例如,由制备实施例获得的下列化合物在500g/ha的施用率下显示出100%的功效:2、9、44、53、55。
在该测试中,例如,制备实施例的下列化合物在500g/ha的施用率下显示出83%的功效:18、34、46。
4.二斑叶螨(Tetranychus urticae)–喷雾测试,OP-抗性
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
为制备合适的活性化合物制剂,使用规定重量份的溶剂来溶解1重量份的活性化合物,并用含有浓度为1000ppm的乳化剂的水调节直至获得所需浓度。为制备其他测试浓度,用含有乳化剂的水稀释所述制剂。
在受到所有阶段的温室红叶螨(二斑叶螨)侵害的菜豆(Phaseolus vulgaris)叶片的叶面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。
在该测试中,例如,制备实施例的下列化合物在500g/ha的施用率下显示出100%的功效:1、2、4、5、6、7、8、9、10、13、14、15、16、17、18、19、20、22、23、26、29、30、31、32、33、34、36、37、39、40、41、44、45、46、47、50、51、52、53、54、55、57、59。
在该测试中,例如,制备实施例的下列化合物在500g/ha的施用率下显示出90%的功效:12、24、28、35、43、48。
5.根结线虫(Meloidogyne incognita)测试
溶剂:7重量份的二甲基甲酰胺
乳化剂:2.5重量份的烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述量的溶剂和乳化剂混合,并将浓液用水稀释至所需浓度,在计算中有必要包括被浸湿的土壤体积。应当确保在土壤中乳化剂的浓度不超过20ppm。为制备其他测试浓度,使用水进行稀释。
用活性化合物溶液喷淋装满土壤(壤砂土)的容器。加入南方根结线虫(根结线虫)的卵/幼虫悬浮液,将莴笋种子散播在土壤表面,并用石英砂将其覆盖。莴笋种子发芽,并长成植物。虫瘿在根部发育。
21天后,通过形成的虫瘿测定以%计的杀线虫功效。100%意指未发现虫瘿;0%意指经处理的植物上的虫瘿数量相当于未处理的对照组。
在该测试中,例如,制备实施例的下列化合物在8ppm的施用率下显示出85%的功效:2。
6.二斑叶螨(Tetranychus urticae)–喷物测试,OP-抗性
溶剂:7重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,使用规定重量份的溶剂来溶解1重量份的活性化合物,并用含有浓度为1000ppm的乳化剂的水调节直至获得所需浓度。为制备其他测试浓度,用含有乳化剂的水稀释所述制剂。如果需要添加铵盐和/或渗透剂,则它们各自以1000ppm的浓度添加到制剂溶液中。
通过喷洒所需浓度的活性化合物制剂来处理受到所有阶段的温室红叶螨(二斑叶螨)严重侵害的菜豆(Phaseolus vulgaris)植株。
7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。
在该测试中,例如,由制备实施例获得的下列化合物在20ppm的施用率下显示出100%的功效:49、56。
对比实施例:
1.辣根猿叶甲(Phaedon cochleariae)-喷雾测试(PHAECO)
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
为制备合适的活性化合物制剂,使用规定重量份的溶剂来溶解1重量份的活性化合物,并用含有浓度为1000ppm的乳化剂的水调节直至获得所需浓度。为制备其他测试浓度,用含有乳化剂的水稀释所述制剂。
在大白菜叶片的叶面上喷洒所需浓度的活性化合物制剂,并在干燥后,接种芥菜甲虫(辣根猿叶甲)的幼虫。
在所需的一段时间后,测定以%计的功效。100%意指所有的甲虫幼虫都已被杀死;0%意指没有甲虫幼虫被杀死。
在该测试中,例如,与4-[6-氧代-4-(三氟甲基)嘧啶-1-基]-2-(2,2,2-三氟乙基亚磺酰基)苄腈和5-氟-4-[6-氧代-4-(三氟甲基)嘧啶-1-基]
-2-(2,2,2-三氟乙基亚磺酰基)苄腈相比,制备实施例的下列化合物显示出优异的功效:参见下文中的表5。
2.二斑叶螨(Tetranychus urticae)–喷雾测试;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
为制备合适的活性化合物制剂,使用规定重量份的溶剂来溶解1重量份的活性化合物,并用含有浓度为1000ppm的乳化剂的水调节直至获得所需浓度。为制备其他测试浓度,用含有乳化剂的水稀释所述制剂。
在受到所有阶段的温室红叶螨(二斑叶螨)侵害的菜豆(Phaseolus vulgaris)叶片的叶面上喷洒所需浓度的活性化合物制剂。
在所需的一段时间后,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。
在该测试中,例如,与4-[6-氧代-4-(三氟甲基)嘧啶-1-基]-2-(2,2,2-三氟乙基亚磺酰基)苄腈和5-氟-4-[6-氧代-4-(三氟甲基)嘧啶-1-基]-2-(2,2,2-三氟乙基亚磺酰基)苄腈相比,制备实施例的下列化合物显示出优异的功效:参见下文中的表5。
表5:
Claims (19)
1.式(I)的化合物
其中
V代表氧或代表硫或代表取代的氮;
Q代表取代的碳或代表氮;
R3和R6彼此独立地
代表氢、卤素、氰基或硝基;或
代表烷基、烯基、炔基、烷氧基、烷基硫烷基、烷基亚磺酰基、烷基磺酰基、卤代烷基羰基、烷基羰基或烷氧基羰基,其中上述基团可任选地被取代;或者
代表环烷基、环烷基烷基或环烯基,其中所述环可包含至少一个选自硫、氧和氮的杂原子,条件是两个氧原子不能直接彼此相邻,其中上述基团可任选地被取代;或者
代表芳基、杂芳基、芳基烷基或杂芳基烷基,其中上述基团可任选地被取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、氰基、烷基、卤代烷基、氰基烷基、羟基烷基、烷氧基烷基、烷基硫烷基烷基、烷基亚磺酰基烷基、烷基磺酰基烷基、烯基、卤代烯基、氰基烯基、炔基、卤代炔基、氰基炔基、酰基或烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成任选地取代的、饱和或不饱和三至八元环,所述环可以任选地被一个以上的独立地选自O、S和N的杂原子间隔,条件是两个氧原子不能直接彼此相邻;或
W代表氢或卤素;
n代表数字0、1或2;
Y代表氢、卤素、(C1-C6)-烷基、三氟甲基、(C2-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基或氨基;或
代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C6)-烷基或(C1-C6)-卤代烷基;
X代表氢、卤素、氰基、(C1-C6)-烷基、(C2-C6)-卤代烷基或(C1-C6)-烷氧基。
2.根据权利要求1所述的化合物,其中
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C3-C6)-环烷基或(C1-C6)-烷氧基;
R3和R6彼此独立地
代表氢、卤素、氰基或硝基;或
代表(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-卤代烷基硫烷基、(C1-C6)-卤代烷基亚磺酰基、(C1-C6)-卤代烷基磺酰基、(C1-C6)-烷基硫烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、(C1-C5)-烷基羰基、(C1-C5)-卤代烷基羰基或(C2-C6)-烷氧基羰基;或者
代表(C3-C6)-环烷基、(C3-C6)-环烷基-(C1-C3)-烷基或(C3-C6)-环烯基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表苯基、杂芳基、苯基-(C1-C3)-烷基或杂芳基-(C1-C3)-烷基,其中上述基团可任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-羟基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C3-C4)-烯基、(C3-C4)-卤素烯基、(C2-C4)-氰基烯基、(C3-C4)-炔基、(C3-C4)-卤代炔基、(C3-C4)-氰基炔基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成任选地被卤素、烷基、氰基、硝基、烷氧基、卤代烷基或卤代烷氧基取代的、饱和或不饱和三至八元环,所述环任选地被一个以上的独立地选自O、S和N的杂原子间隔,条件是两个氧原子不能直接彼此相邻;或
W代表氢或卤素;
n代表数字0或1;
Y代表氢、卤素、(C1-C4)-烷基、三氟甲基、(C2-C4)-卤代烷基、
(C1-C4)-烷氧基、(C1-C4)-卤代烷氧基或氨基;或
代表NR“‘R““,
其中R“‘和R““彼此独立地代表氢、(C1-C4)-烷基或(C2-C4)-卤代烷基;
X代表氢、卤素、氰基、(C1-C4)-烷基、(C1-C4)-卤代烷基或(C1-C4)-烷氧基。
3.根据权利要求1或2所述的化合物,其中
V代表氧;
Q代表C-R5或氮,其中
R5代表氢、卤素、氨基、氰基、硝基、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C3-C6)-环烷基或(C1-C4)-烷氧基;
R3和R6彼此独立地
代表氢或卤素;或
代表(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-烷氧基或(C1-C4)-卤代烷氧基;或者
代表(C3-C6)-环烷基或(C3-C6)-环烷基-(C1-C2)-烷基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基取代;或者
代表苯基或苯基-(C1-C3)-烷基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表选自下列的杂芳基:呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、吲哚基、异吲哚基和吲唑基,其中上述基团可任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代;或者
代表NR‘R“,
其中R‘和R“彼此独立地代表氢、(C1-C4)-烷基、(C1-C4)-卤代烷基、(C1-C4)-氰基烷基、(C1-C4)-烷氧基-(C1-C4)-烷基、(C1-C4)-烷基硫烷基-(C1-C4)-烷基、(C1-C4)-烷基亚磺酰基-(C1-C4)-烷基、(C1-C4)-烷基磺酰基-(C1-C4)-烷基、(C1-C4)-烷基羰基或(C1-C4)-烷氧基羰基;
或
其中R‘和R“连同它们所连接的氮原子一起可形成饱和的四至六元环,所述环任选地被氟、氯、溴、碘、(C1-C3)-烷基、氰基、硝基、(C1-C3)-烷氧基、(C1-C3)-卤代烷基或(C1-C3)-卤代烷氧基单取代或二取代,以及任选地被选自O、S和N的杂原子间隔;
W代表氢或氟;
n代表数字0或1;
Y代表氢、氟、氯、溴、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、氨基、甲基氨基或二甲基氨基;
X代表氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基或乙氧基。
4.根据权利要求1至3中任一项所述的化合物,其中
V代表氧;
Q代表C-R5,其中
R5代表氢、甲基、乙基、甲氧基、环丙基或三氟甲基;
R3和R6彼此独立地代表氢、氟、甲基、乙基、异丙基、三氟甲基、五氟乙基、二氟甲基、1,1-二氟乙基、二氟氯甲基、环丙基或苯基;
W代表氢或氟;
n代表数字0或1;
Y代表氟、氯、溴、甲基、三氟甲基或甲氧基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,F)、(Me,H)、(Me,Cl)、(Me,Me)、(Cl,Cl)、(Cl,F)、(MeO,F)、(MeO,H)、(Cl,H)、(Br,H)、(Br,F)、(F,F)、(CF3,H)、(CF3,F)。
5.根据权利要求1至4中任一项所述的化合物,其中
V代表氧;
Q代表C-R5,其中
R5代表氢或甲基;
R3代表氢、甲基、乙基、环丙基、异丙基、二氟甲基、三氟甲基、五氟乙基、1,1-二氟乙基或苯基;
R6代表氢、氟或甲基;
W代表氟;
n代表数字0或1;
Y代表溴、氯或甲基;
X代表氢、氯、氟或甲基;
其中X和Y特别是代表下列组合(Y,X):(Me,H)、(Me,Cl)、(Me,F)、(Me,Me)、(Cl,Cl)、(Cl,F)、(Br,F)。
6.根据权利要求1至5中任一项所述的化合物,其中Q代表C-R5,以及R5、R3、R6、W、n、Y和X具有权利要求2中定义的含义或权利要求3中定义的含义或权利要求4中定义的含义或权利要求5中定义的含义。
7.式(IIa)的化合物,
其中R3、R6、W、X和Y具有权利要求1中定义的含义或权利要求2中定义的含义或权利要求3中定义的含义或权利要求4中定义的含义或权利要求5中定义的含义。
8.式(XXXI)的化合物,
其中R3、R6、W、X和Y具有权利要求1中定义的含义或权利要求2中定义的含义或权利要求3中定义的含义或权利要求4中定义的含义或权利要求5中定义的含义。
9.制剂,特别是农用化学制剂,其包含至少一种根据权利要求1至6中任一项所述的式(I)的化合物。
10.根据权利要求9所述的制剂,其还包含至少一种增量剂和/或至少一种表面活性物质。
11.根据权利要求9或10所述的制剂,其特征在于式(I)的化合物与至少一种其他活性化合物混合。
12.防治害虫,尤其是动物害虫的方法,其特征在于使根据权利要求1至6中任一项所述的式(I)的化合物或根据权利要求9至11中任一项所述的制剂作用于害虫和/或它们的栖息地。
13.根据权利要求12所述的方法,其特征在于所述害虫为动物害虫,并且包括昆虫、螨或线虫;或其特征在于所述害虫为昆虫、螨或线虫。
14.根据权利要求1至6中任一项所述的式(I)的化合物或根据权利要求9至11中任一项所述的制剂用于防治动物害虫的用途。
15.根据权利要求14所述的方法,其特征在于所述动物害虫包括昆虫、螨或线虫;或其特征在于所述动物害虫为昆虫、螨或线虫。
16.根据权利要求14或15所述的在作物保护中的用途。
17.根据权利要求14或15所述的在动物健康领域中的用途。
18.保护种子或发芽植物免受害虫,特别是动物害虫的方法,其包括下列方法步骤:其中使种子与根据权利要求1至6中任一项所述的式(I)的化合物或根据权利要求9至11中任一项所述的制剂接触。
19.通过根据权利要求18所述的方法得到的种子。
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RU2748695C2 (ru) * | 2016-07-07 | 2021-05-28 | Сумитомо Кемикал Компани, Лимитед | Гетероциклическое соединение и содержащее его средство для борьбы с вредными членистоногими |
TW201841890A (zh) * | 2017-04-05 | 2018-12-01 | 日商阿格諾卡那休股份有限公司 | 新穎1-苯基哌啶衍生物及以其為有效成份之農園藝用藥劑 |
WO2019079369A1 (en) | 2017-10-19 | 2019-04-25 | Effector Therapeutics, Inc. | BENZIMIDAZOLE INDOLE INHIBITORS OF MNK1 AND MNK2 |
US11180754B2 (en) | 2017-12-15 | 2021-11-23 | Cj Cheiljedang Corporation | Polypeptide and method of producing IMP using the same |
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