CN106795140A - 新的卤素取代的化合物 - Google Patents
新的卤素取代的化合物 Download PDFInfo
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- CN106795140A CN106795140A CN201580054567.XA CN201580054567A CN106795140A CN 106795140 A CN106795140 A CN 106795140A CN 201580054567 A CN201580054567 A CN 201580054567A CN 106795140 A CN106795140 A CN 106795140A
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
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- JUVIOZPCNVVQFO-HBGVWJBISA-N rotenone Chemical compound O([C@H](CC1=C2O3)C(C)=C)C1=CC=C2C(=O)[C@@H]1[C@H]3COC2=C1C=C(OC)C(OC)=C2 JUVIOZPCNVVQFO-HBGVWJBISA-N 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
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- 239000003352 sequestering agent Substances 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- WESJNFANGQJVKA-UHFFFAOYSA-M sodium;2,3-dichloro-2-methylpropanoate Chemical compound [Na+].ClCC(Cl)(C)C([O-])=O WESJNFANGQJVKA-UHFFFAOYSA-M 0.000 description 1
- 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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- 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
- 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
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- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical class CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- 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
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JPLIYTCALCWKAS-UHFFFAOYSA-N triphenyl-$l^{3}-chlorane Chemical compound C1=CC=CC=C1Cl(C=1C=CC=CC=1)C1=CC=CC=C1 JPLIYTCALCWKAS-UHFFFAOYSA-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
- VRNFXUOQGOAQBZ-DYXAMGHASA-N veratrin Chemical compound C1[C@@H](C)CC[C@H]2[C@](O)(C)[C@@]3(O)[C@@H](O)C[C@@]4(O)[C@@H]5CC[C@H]6[C@]7(C)CC[C@H](OC(=O)C(\C)=C/C)[C@@]6(O)O[C@@]75C[C@@]4(O)[C@@H]3CN21.C1=C(OC)C(OC)=CC=C1C(=O)O[C@@H]1[C@@]2(O)O[C@@]34C[C@@]5(O)[C@H](CN6[C@@H](CC[C@H](C)C6)[C@@]6(C)O)[C@]6(O)[C@@H](O)C[C@@]5(O)[C@@H]4CC[C@H]2[C@]3(C)CC1 VRNFXUOQGOAQBZ-DYXAMGHASA-N 0.000 description 1
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Classifications
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
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Abstract
本发明尤其涉及卤素‑取代的通式(I)化合物,其中取代基A1、R1‑R3和Z1‑Z3具有说明书中所给出的含义。还描述了用于制备通式(I)化合物的方法和用于制备这些化合物的可能的中间体。本发明的化合物特别适合在农业中用于防治昆虫、蛛形纲动物和线虫以及在兽医中防治外寄生虫。
Description
技术背景
本申请涉及新的卤素取代的化合物、其制备方法以及其用于防治动物有害生物的用途,特别是节肢动物,且尤其是昆虫、蛛形纲动物和线虫。
已知某些卤素取代的化合物具有除草作用(参见J.Org.Chem.1997,62(17),5908-5919;J.Heterocycl.Chem.1998,35(6),1493-1499;WO 2004/035545;WO 2004/106324;US2006/069132;WO 2008/029084)。
此外,已知某些卤素取代的化合物具有杀昆虫作用(EP 1 911 751、WO2012/069366、WO2012/080376&WO2012/107434)。
另外,已知某些卤素取代的化合物具有细胞因子抑制活性(WO 2000/07980)。
现代作物保护组合物必须满足许多需求,例如关于它们作用的功效、持久性和作用谱以及可能的用途。毒性问题、与其它活性化合物或制剂助剂的可组合性以及活性化合物合成所需的费用问题很关键。此外,可能产生抗性。由于所有这些原因,决不能认为对新的作物保护剂的探寻已经完成,而是存在着对具有与已知化合物相比至少在个别方面得以改进的性质的新化合物的持续的需求。
本发明的一个目的是提供在各方面拓宽农药作用谱和/或改进它们的活性的化合物。
出人意料地,现已发现,某些卤素取代的化合物及其N-氧化物和盐具有生物活性且特别适合用于防治动物有害生物,因此可特别好地用于农业化学领域和动物健康领域。
类似的化合物已知于WO 2010/051926。
发明内容
本发明的一个方面涉及通式(I)的化合物,
其中
Z1代表1-卤化的环丙基;
Z2代表-S(O)0-2-(C1-C2)-烷基、(C1-C2)-卤代烷基或硝基(NO2);
Z3代表(C1-C2)-烷基;
R1代表氢(H)或(C1-C2)-烷基;
R2代表H或氰基(CN);
R3代表CH3或氯(Cl);
A1代表CH或氮(N)。
技术人员会理解,本发明的所有实施方案皆可组合。排除违反自然规律的部分组合。
在一个优选的实施方案中,在式(I)化合物中A1为CH(同时所有其他取代基均如上文所定义)。
在另一个优选实施方案中,在式(I)化合物中A1为CH且R3为Cl(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF3、Cl、Br、I或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为-S-CH3、Cl、Br、I、CF3或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为I、CF3或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为氟化甲基(CF3CF2H或CFH2)或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为CF3、CF2H或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为CF2H或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为CF3或NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为S(O)0、1或2-CH3;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为S-CH3;
Z3为CH3(同时所有其他取代基均如上文所定义)。在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为S(O)1-CH3;
Z3为CH3(同时所有其他取代基均如上文所定义)。在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为S(O)2-CH3;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为NO2;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为CF3;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中
Z1为1-氟-环丙基或1-氯-环丙基或1-溴环丙基;
Z2为CF2H;
Z3为CH3(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中R1为H(同时所有其他取代基均如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中A1为N(同时Z1、Z2、Z3、R1、R2和R3如上文所定义)。
在又一个优选实施方案中,在式(I)化合物中R3为Cl(同时所有其他取代基均如上文所定义)。
另一方面涉及本发明的化合物用于防治昆虫、蛛形纲动物和线虫的用途。
又一个方面涉及包含至少一种本发明的化合物的药物组合物。
又一个方面涉及一种用作药物的本发明的化合物。
又一个方面涉及本发明的化合物用于制备用于防治动物寄生虫的药物组合物的用途。
又一个方面涉及一种用于制备作物保护组合物的方法,所述作物保护组合物包含本发明的化合物以及常规增量剂和/或表面活性剂。
又一个方面涉及选自如本文所描述的化合物(10)、(11)、(12)、(13)、(14)和(24)的化合物。
又一个方面涉及式(10)的化合物。
又一个方面涉及式(11)的化合物。
又一个方面涉及式(12)的化合物。
又一个方面涉及式(13)的化合物。
又一个方面涉及式(14)的化合物。
又一个方面涉及式(24)的化合物。
又一个方面涉及一种用于制备式(I)化合物的方法,包括制备如本文所述的式(10)、(11)、(12)、(13)和(14)化合物的步骤。
又一个方面涉及防治有害生物的方法,其特征在于使本发明的化合物作用于有害生物和/或它们的生境。
又一个方面涉及本发明的化合物用于保护植物的繁殖材料的用途。
定义
根据本发明,“烷基”——其本身或作为化学基团的一部分——代表优选具有1至6个碳原子的直链或支链烃,例如,甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基,1-乙基丙基,己基,1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丙基、1,3-二甲基丁基、1,4-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基和2-乙基丁基。此外优选具有1至2个碳原子的烷基基团。
根据本发明,“卤素(halogen)”或“卤(halo)”代表氟、氯、溴或碘,特别是氟、氯或溴。
本发明的卤素取代的化学基团,例如,卤代烷基为单取代或为被最高达取代基的最大可能数目(全卤代)的卤素多取代。如果被卤素多取代,则卤素原子可相同或不同,且可连接至碳原子中的一个或多个。在本文中,卤素具体代表氟、氯、溴或碘,优选氟、氯或溴且特别优选氟。
根据本发明,“环烷基”——其本身或作为化学基团的一部分——代表优选具有3个碳原子的单环烃(环丙基)。本发明的环烷基可被一种或多种相同或不同的基团取代。
根据本发明,“卤代烷基(halogenalkyl)”、“卤代环烷基(halogencycloalkyl)”、“卤化烷基(halogenated alkyl)”和“卤化环烷基(halogenated cycloalkyl)”代表优选具有1至5个相同或不同卤素原子的卤素取代的烷基/环烷基,例如,单卤代烷基例如CH2CH2Cl、CH2CH2F、CHClCH3、CHFCH3、CH2Cl、CH2F;单卤代环烷基例如1-氟-环烷基或1-氯-环烷基;全卤代烷基例如CCl3或CF3或CF2CF3;多卤代烷基例如CHF2、CH2F、CH2CHFCl、CHCl2、CF2CF2H、CH2CF3。
根据取代基的性质,本发明的化合物可为几何异构体和/或光学活性异构体的形式或相应的具有不同组成的异构体混合物。这些立体异构体为例如对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明既涵盖纯的立体异构体也涵盖这些异构体的任意混合物。
如果合适,本发明的化合物可以各种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皆由本发明提供且可根据本发明使用。
具体实施方式
本发明的卤素取代的化合物通过通式(I)定义
其中
Z1代表1-卤化的环丙基;
Z2代表-S(O)0-2-(C1-C2)-烷基、(C1-C2)-卤代烷基或硝基(NO2);
Z3代表(C1-C2)-烷基;
R1代表氢(H)或(C1-C2)-烷基;
R2代表H或氰基(CN);
R3代表CH3或氯(Cl);
A1代表CH或氮(N)。
在下述优选实施方案中,如果在所述优选实施方案中没有另外定义,则式(I)化合物的任意取代基R1至R3、A1、Z1至Z3均具有上述这一段落中所定义的含义。普通技术人员会理解,优选实施方案可组合,只要该组合不违背现有的自然规律。
在一个优选的实施方案中A1为CH。
在另一个优选实施方案中A1为CH且R3为Cl。
在另一个优选实施方案中Z3为CH3。
在另一个优选实施方案中Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF3、CF2H、Cl、Br、I或NO2。
在另一个优选实施方案中Z2为-S-CH3、Cl、Br、I、CF3、CF2H或NO2。
在另一个优选实施方案中,Z2为-S(O)0-2-CH3、CF3,
在另一个优选实施方案中Z2为I、CF2H、CF3或NO2。
在另一个优选实施方案中Z1为1-氟-环丙基或1-氯-环丙基。
在另一个优选实施方案中
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中,R1为H或CH3。
在另一个优选实施方案中,R1为H。
在另一个优选实施方案中,R1为CH3
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、
或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中,A1为N。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中R2为H。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中R2为CN。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF3、CF2H、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为Cl,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中A1为CH且R3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为H,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为CH,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I、或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为H,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氟-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF2H、CF3、Cl、Br、I或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为-S-CH3、Cl、Br、I、CF2H、CF3或NO2,且
Z3为CH3。
在另一个优选实施方案中
R1为CH3,
R2为CN,
A1为N,
R3为CH3,
Z1为1-氯-环丙基,
Z2为I、CF2H、CF3或NO2,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-卤-环丙基,优选1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-S-C1-C3-烷基、氟化C1-C3-烷基或NO2,优选-S-CH3、-CF3、-CF2H、-CFH2或-NO2,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-S-C1-C3-烷基,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-S-CH3,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为氟化C1-C3-烷基,优选氟化甲基,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-CF3、-CF2H、-CFH2且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-CF3,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-CF2H,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,
Z2为-NO2,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为N或C-H,优选C-H,
R3为Cl或Me,优选Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,甚至更优选1-氟-环丙基或1-氯-环丙基,
Z2为CF3,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物其中
R1为H,
R2为CN或H,
A1为C-H,
R3为Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为CF3,且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H或N,优选C-H,
R3为Cl或Me,优选Cl,
Z1为1-氟-环丙基、1-氯-环丙基、1-溴-环丙基或1-碘-环丙基,更优选1-氟-环丙基、1-氯-环丙基或1-溴-环丙基,甚至更优选1-氟-环丙基或1-氯-环丙基,
Z2为S(=O)n-(CH3),且
Z3为CH3。
又一个优选的实施方案涉及式(I)化合物
其中
R1为H,
R2为CN或H,
A1为C-H
R3为Cl或Me,优选Cl,
Z1为1-氟-环丙基或1-氯-环丙基,
Z2为S(=O)n-(CH3),且
Z3为CH3。
本发明的化合物可通过本领域普通技术人员已知的常规方法制备。
异构体
根据取代基的性质,式(I)化合物可为几何异构体和/或光学活性异构体的形式或相应的具有不同组成的异构体混合物。这些立体异构体为例如对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明既涵盖纯的立体异构体也涵盖这些异构体的任意混合物。
方法和用途
本发明还涉及用于防治动物有害生物的方法,其中使式(I)化合物作用于动物有害生物和/或它们的生境。动物有害生物的防治优选在农业和林业以及在材料保护中进行。优选从中排除用于人体或动物体的手术性或治疗性处理的方法以及在人体或动物体上进行的诊断方法。
此外,本发明涉及式(I)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,在每种情况下,术语“农药”还始终包括术语“作物保护剂”。
具有良好的植物耐受性、有利的恒温动物毒性和良好的环境相容性的式(I)化合物适合用于保护植物和植物器官抵抗生物胁迫因子和非生物胁迫因子,增加采收产量,提高采收材料的品质,以及防治在农业、园艺业、畜牧业、水产业、林业、园林和休闲设施中、在储存产品的保护和材料的保护中以及在卫生领域中遇到的动物有害生物,特别是昆虫、蛛形纲动物、蠕虫、线虫和软体动物。它们可优选用作农药。它们对通常敏感的且具有抗性的物种具有活性以及对发育的所有阶段或某些阶段具有活性。上述有害生物包括:
节肢动物门(Arthropoda)的有害生物,尤其是蛛形纲(Arachnida),例如,粉螨属(Acarus spp.),例如粗脚粉螨(Acarus siro);枸杞瘤瘿螨(Aceria kuko)、桔芽瘿螨(Aceria sheldoni);刺皮瘿螨属(Aculops spp.);针刺瘿螨属(Aculus spp.),例如佛氏刺瘿螨(Aculus fockeui)、苹果刺瘿螨(Aculus schlechtendali);钝眼蜱属(Amblyommaspp.);山楂叶螨(Amphitetranychus viennensis);锐缘蜱属(Argas spp.);牛蜱属(Boophilus spp.);短须螨属(Brevipalpus spp.),例如紫红短须螨(Brevipalpusphoenicis);蚜苔螨(Bryobia graminum)、苜蓿苔螨(Bryobia praetiosa);刺尾蝎属(Centruroides spp.);皮螨属(Chorioptes spp.);鸡皮刺螨(Dermanyssus gallinae);欧洲屋尘螨(Dermatophagoides pteronyssinus)、美洲粉尘螨(Dermatophagoidesfarinae);革蜱属(Dermacentor spp.);始叶螨属(Eotetranychus spp.),例如核桃始叶螨(Eotetranychus hicoriae);梨上瘿螨(Epitrimerus pyri);真叶螨属(Eutetranychusspp.),例如班氏真叶螨(Eutetranychus banksi);瘿螨属(Eriophyes spp.),例如梨瘿螨(Eriophyes pyri);家甜食螨(Glycyphagus domesticus);红足海镰螯螨(Halotydeusdestructor);半跗线螨属(Hemitarsonemus spp.),例如荼半跗线螨(Hemitarsonemuslatus)(=Polyphagotarsonemus latus);璃眼蜱属(Hyalomma spp.);硬蜱属(Ixodesspp.);毒蛛属(Latrodectus spp.);斜蛛属(Loxosceles spp.);秋收恙螨(Neutrombiculaautumnalis);Nuphersa属;小爪螨属(Oligonychus spp.),例如Oligonychusconiferarum、冬青小爪螨(Oligonychus ilicis)、甘蔗小爪螨(Oligonychus indicus)、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychus pratensis)、石榴小爪螨(Oligonychus punicae)、樟小爪螨(Oligonychus yothersi);纯缘蜱属(Ornithodorusspp.);禽剌螨属(Ornithonyssus spp.);全爪螨属(Panonychus spp.),例如柑桔全爪螨(Panonychus citri)(=Metatetranychus citri)、苹果全爪螨(Panonychus ulmi)(=Metatetranychus ulmi);柑柑锈螨(Phyllocoptruta oleivora);多趾宽叶螨(Platytetranychus multidigituli);侧多食跗线螨(Polyphagotarsonemus latus);痒螨属(Psoroptes spp.);扇头蜱属(Rhipicephalus spp.);根嗜螨属(Rhizoglyphus spp.);疥螨属(Sarcoptes spp.);中东金蝎(Scorpio maurus);狭跗线螨属(Steneotarsonemusspp.),稻细螨(Steneotarsonemus spinki);跗线螨属(Tarsonemus spp.),例如乱跗线螨(Tarsonemus confusus)、樱草狭跗线螨(Tarsonemus pallidus);叶螨属(Tetranychusspp.),例如加拿大叶螨(Tetranychus canadensis)、红叶螨(Tetranychuscinnabarinus)、土耳其斯坦叶螨(Tetranychus turkestani)、二斑叶螨(Tetranychusurticae);阿氏真恙螨(Trombicula alfreddugesi);Vaejovis spp.;番茄斜背瘤瘿螨(Vasates lycopersici);
唇足亚纲(Chilopoda),例如,地蜈蚣属(Geophilus spp.)、蚰蜒属(Scutigeraspp.);
弹尾目或弹尾纲(Collembola),例如,武装棘跳虫(Onychiurus armatus)、绿圆跳虫(Sminthurus viridis);
倍足纲(Diplopoda),例如,千足虫(Blaniulus guttulatus);
昆虫纲(Insecta),例如蜚蠊目(Blattodea),例如,东方蜚蠊(Blattaorientalis);亚洲蜚蠊(Blattella asahinai)、德国蜚蠊(Blattella germanica);马德拉蜚蠊(Leucophaea maderae);古巴蠊属(Panchlora spp.);木蠊属种(Parcoblatta spp.);大蠊属(Periplaneta spp.),例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplaneta australasiae);棕带蜚蠊(Supella longipalpa);
鞘翅目(Coleoptera),例如,条纹南瓜甲虫(Acalymma vittatum);菜豆象(Acanthoscelides obtectus);喙丽金龟属(Adoretus spp.);杨树萤叶甲(Agelasticaalni);叩甲属(Agriotes spp.),例如直条叩头虫(Agriotes linneatus)、小麦叩头虫(Agriotes mancus);黑菌虫(Alphitobius diaperinus);马铃薯鳃角金龟(Amphimallonsolstitialis);家具窃蠹(Anobium punctatum);星天牛属(Anoplophora spp.);花象属(Anthonomus spp.),例如棉铃象甲(Anthonomus grandis);圆皮蠹属(Anthrenus spp.);梨象属(Apion spp.);阿鳃金龟属(Apogonia spp.);隐食甲属(Atomaria spp.),例如甜菜隐食甲(Atomaria linearis);毛皮蠹属(Attagenus spp.);Baris caerulescens;恶条豆象(Bruchidius obtectus);豆象属(Bruchus spp.),例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus);龟叶甲属(Cassida spp.);菜豆莹叶甲(Cerotoma trifurcata);龟象属(Ceutorrhynchus spp.),例如白菜籽龟象(Ceutorrhynchus assimilis)、甘蓝茎龟象(Ceutorrhynchus quadridens)、Ceutorrhynchus rapae;跳甲属(Chaetocnema spp.),例如甘薯跳甲(Chaetocnema confinis)、美国齿跳甲(Chaetocnema denticulata)、荒地玉米跳甲(Chaetocnema ectypa);Cleonus mendicus;宽胸叩头虫属(Conoderus spp.);根颈象属(Cosmopolites spp.),例如香蕉根茎象甲(Cosmopolites sordidus);褐新西兰肋翅鳃角金龟(Costelytra zealandica);叩甲属(Ctenicera spp.);象虫属(Curculio spp.),例如美核桃象(Curculio caryae)、大栗象(Curculio caryatrypes)、美洲榛子象(Curculio obtusus)、小栗象(Curculio sayi);锈赤扁谷盗(Cryptolestesferrugineus)、长角扁谷盗(Cryptolestes pusillus);杨干隐喙象(Cryptorhynchuslapathi)、芒果果核象甲(Cryptorhynchus mangiferae);细枝象属(Cylindrocopturusspp.),密点细枝象(Cylindrocopturus adspersus)、洋松细枝象(Cylindrocopturusfurnissi);皮蠹属(Dermestes spp.);叶甲属(Diabrotica spp.),例如带斑黄瓜条叶甲(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(Diabroticaundecimpunctata undecimpunctata)、西方玉米根叶甲(Diabrotica virgiferavirgifera)、墨西哥玉米根叶甲(Diabrotica virgifera zeae);蛀野螟属种(Dichocrocisspp.);水稻铁甲(Dicladispa armigera);Diloboderus spp.;食植瓢虫属(Epilachnaspp.),例如瓜食植瓢虫(Epilachna borealis)、墨西哥豆瓢虫(Epilachna varivestis);毛跳甲属(Epitrix spp.),例如黄瓜跳甲(Epitrix cucumeris)、茄子跳甲(Epitrixfuscula)、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrix tuberis);钻孔虫属(Faustinus spp.);裸蛛甲(Gibbium psylloides);阔角谷盗(Gnathocerus cornutus);菜心野螟(Hellula undalis);黑异爪蔗金龟(Heteronychus arator);寡节鳃金龟属(Heteronyx spp.);Hylamorpha elegans;北美家天牛(Hylotrupes bajulus);紫苜蓿叶象(Hypera postica);蓝绿象(Hypomecessquamosus);咪小蠹属(Hypothenemus spp.),例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemus obscurus)、毛竹小蠹(Hypothenemus pubescens);甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea);烟草甲(Lasioderma serricorne);长头谷盗(Latheticus oryzae);波缘薪甲属(Lathridius spp.);负泥虫属(Lema spp.);马铃薯甲虫(Leptinotarsa decemlineata);潜叶蛾属(Leucoptera spp.),例如咖啡潜叶蛾(Leucoptera coffeella);稻根象(Lissorhoptrus oryzophilus);筒喙象属(Lixusspp.);黄胸寡毛跳甲(Luperomorpha xanthodera);萤叶甲属(Luperodes spp.);粉蠹属种(Lyctus spp.);美洲叶甲属(Megascelis spp.);梳爪叩头虫属(Melanotus spp.),例如Melanotus longulus oregonensis;油菜花露尾甲(Meligethes aeneus);鳃金龟属(Melolontha spp.),例如欧洲鳃金龟(Melolontha melolontha);Migdolus spp.;墨天牛属(Monochamus spp.);象甲(Naupactus xanthographus);隐跗郭公虫属(Necrobiaspp.);黄蛛甲(Niptus hololeucus);椰蛀犀金龟(Oryctes rhinoceros);锯谷盗(Oryzaephilus surinamensis);Oryzaphagus oryzae;耳喙象属(Otiorhynchus spp.),例如苹果耳喙象(Otiorhynchus cribricollis)、苜蓿耳喙象(Otiorhynchus ligustici)、草莓耳喙象(Otiorhynchus ovatus)、粗糙草莓耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳喙象(Otiorhynchus sulcatus);小青花金龟(Oxycetonia jucunda);辣根猿叶虫(Phaedon cochleariae);食叶鳃金龟属(Phyllophaga spp),鳃金龟(Phyllophagahelleri);黄条跳甲属(Phyllotreta spp.),例如辣根菜跳甲(Phyllotreta armoraciae)、西方黑跳甲(Phyllotreta pusilla)、美条纹跳甲(Phyllotreta ramosa)、黄曲条跳甲(Phyllotreta striolata);日本丽金龟(Popillia japonica);象甲属(Premnotrypesspp.);大谷蠹(Prostephanus truncatus);跳甲属(Psylliodes spp.),例如马铃薯跳甲(Psylliodes affinis)、油菜金头跳甲(Psylliodes chrysocephala)、忽布跳甲(Psylliodes punctulata);蛛甲属(Ptinus spp.);暗色瓢虫(Rhizobius ventralis);谷蠹(Rhizopertha dominica);谷象属(Sitophilus spp.),例如谷象(Sitophilusgranarius)、罗望子象(Sitophilus linearis)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais);尖隐喙象属(Sphenophorus spp.);药材甲(Stegobiumpaniceum);茎干象属(Sternechus spp.),例如豆茎象(Sternechus paludatus);宽幅天牛属(Symphyletes spp.);纤毛象属种(Tanymecus spp.),例如双宽隆突纤毛象(Tanymecusdilaticollis)、印度纤毛象(Tanymecus indicus)、红豆草灰象甲(Tanymecuspalliatus);黄粉虫(Tenebrio molitor);大谷盗(Tenebrioides mauretanicus);拟谷盗属(Tribolium spp.),例如美洲黑拟谷盗(Tribolium audax)、赤拟谷盗(Triboliumcastaneum)、杂拟谷盗(Tribolium confusum);斑皮蠹属(Trogoderma spp.);籽象属(Tychius spp.);脊虎天牛属(Xylotrechus spp.);距步甲属(Zabrus spp.),例如玉米距步甲(Zabrus tenebrioides);
双翅目(Diptera),例如,伊蚊属(Aedes spp.),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、刺扰伊蚊(Aedes vexans);潜蝇属(Agromyza spp.),例如苜蓿斑潜蝇(Agromyza frontella)、美洲黍潜蝇(Agromyzaparvicornis);按实蝇属(Anastrepha spp.);按蚊属(Anopheles spp.),例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae);瘿蚊属(Asphondyliaspp.);果实蝇属(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(Bibiohortulanus);天青丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina);地中海实蝇(Ceratitis capitata);摇蚊属(Chironomus spp.);金蝇属(Chrysomyaspp.);斑虻属种Chrysops spp.);高额麻虻(Chrysozona pluvialis);锥蝇属(Cochliomyaspp.);康瘿蚊属(Contarinia spp.),例如葡萄瘿蚊(Contarinia johnsoni)、甘蓝瘿蚊(Contarinia nasturtii)、梨叶瘿蚊(C ontarinia pyrivora)、向日葵瘿蚊(Contariniaschulzi)、高粱瘿蚊(Contarinia sorghicola)、麦黄康瘿蚊(Contarinia tritici);嗜人瘤蝇(Cordylobia anthropophaga);环足摇蚊(Cricotopus sylvestris);库蚊属(Culexspp.),例如尖音库蚊(Culex pipiens)、致倦库蚊(Culex quinquefasciatus);库蠓属(Culicoides spp.);脉毛蚊属(Culiseta spp.);黄蝇属(Cuterebra spp.);橄榄实蝇(Dacus oleae);叶瘿蚊属(Dasineura spp.),例如油菜荚叶瘿蚊(Dasineura brassicae);地种蝇属(Delia spp.),例如葱地种蝇(Delia antiqua)、麦地种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum);人皮蝇(Dermatobia hominis);果蝇属(Drosophila spp.),例如黄猩猩果蝇(Drosphilamelanogaster)、樱桃果蝇(Drosophila suzukii);稻象属(Echinocnemus spp.);厕蝇属(Fannia spp.);胃蝇属(Gasterophilus spp.);舌蝇属(Glossina spp.);麻虻属(Haematopota spp.);毛眼水蝇属(Hydrellia spp.);大麦毛眼水蝇(Hydrelliagriseola);种蝇属(Hylemya spp.);虱蝇属(Hippobosca spp.);皮下蝇属(Hypodermaspp.);斑潜蝇属(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(Lucilia spp.),例如铜绿蝇(Lucilia cuprina);罗蛉属(Lutzomyia spp.);曼蚊属(Mansonia spp.);家蝇属(Musca spp.),例如家蝇(Musca domestica)、舍蝇(Musca domestica vicina);狂蝇属(Oestrus spp.);瑞典麦秆蝇(Oscinella frit);拟长跑摇蚊属(Paratanytarsus spp.);Paralauterborniella subcincta;泉蝇属(Pegomya spp.),例如甜菜蝇(Pegomya betae)、天仙子泉蝇(Pegomya hyoscyami)、悬钩子泉蝇(Pegomya rubivora);白蛉属(Phlebotomusspp.);草种蝇属(Phorbia spp.);伏蝇属(Phormia spp.);酪蝇(Piophila casei);Prodiplosis spp.;胡萝卜茎蝇(Psila rosae);绕实蝇属(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(Rhagoletis indifferens)、蓝橘绕实蝇(Rhagoletis mendax)、苹果实蝇(Rhagoletis pomonella);麻蝇属(Sarcophaga spp.);蚋属(Simulium spp.),例如南方蚋(Simulium meridionale);螫蝇属(Stomoxys spp.);虻属(Tabanus spp.);根斑蝇属(Tetanops spp.);大蚊属(Tipula spp.),例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex);
半翅目(Hemiptera),例如,Acizzia acaciaebaileyanae、Acizzia dodonaeae、Acizzia uncatoides;长头蝗(Acrida turrita);无网长管蚜属(Acyrthosipon spp.),例如碗豆长管蚜(Acyrthosiphon pisum);Acrogonia spp.;沫蝉属(Aeneolamia spp.);隆脉木虱属(Agonoscena spp.);欧洲甘蓝粉虱(Aleyrodes proletella);甘蔗穴粉虱(Aleurolobus barodensis);软毛粉虱(Aleurothrixus floccosus);Allocaridaramalayensis;芒果叶蝉属(Amrasca spp.),例如小绿叶蝉(Amrasca bigutulla)、小叶蝉(Amrasca devastans);飞廉短尾蚜(Anuraphis cardui);肾圆盾蚧属(Aonidiella spp.),例如红肾圆盾蚧(Aonidiella aurantii)、黄肾圆盾蚧(Aonidiella citrina)、苏铁肾盾蚧(Aonidiella inornata);苏联黄粉蚜(Aphanostigma piri);蚜属(Aphis spp.),例如苹果黄蚜(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(Aphis gossypii)、常春藤蚜(Aphishederae)、葡萄藤蚜(Aphis illinoisensis)、Aphis middletoni、鼠李马铃薯蚜(Aphisnasturtii)、夹竹桃蚜(Aphis nerii)、苹果蚜(Aphis pomi)、绣线菊蚜(Aphisspiraecola)、Aphis viburniphila;葡萄叶蜂(Arboridia apicalis);Arytainilla spp.;小圆盾蚧属种(Aspidiella spp.);圆盾蚧属(Aspidiotus spp.),例如常春藤圆盾蚧(Aspidiotus nerii);Atanus spp.;茄沟无网蚜(Aulacorthum solani);烟粉虱(Bemisiatabaci);澳大利亚木虱(Blastopsylla occidentalis);Boreioglycaspis melaleucae;李短尾蚜(Brachycaudus helichrysii);微管蚜属(Brachycolus spp.);甘蓝蚜(Brevicoryne brassicae);喀木虱属(Cacopsylla spp.),例如梨木虱(Cacopsyllapyricola);小褐稻虱(Calligypona marginata);黄头大叶蝉(Carneocephala fulgida);甘蔗绵蚜(Ceratovacuna lanigera);沫蝉科(Cercopidae);蜡蚧属(Ceroplastes spp.);草莓钉蚜(Chaetosiphon fragaefolii);蔗黄雪盾蚧(Chionaspis tegalensis);荼绿叶蜂(Chlorita onukii);台湾大蝗(Chondracris rosea);核桃黑斑蚜(Chromaphisjuglandicola);黑褐圆盾蚧(Chrysomphalus ficus);玉米叶蝉(Cicadulina mbila);Coccomytilus halli;软蚧属(Coccus spp.),例如褐软蚧(Coccus hesperidum)、长椭圆软蚧(Coccus longulus)、橘软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿软蚧(Coccusviridis);隐瘤蚜(Cryptomyzus ribis);Cryptoneossa spp.;Ctenarytaina spp.;角顶叶蝉属(Dalbulus spp.);柑橘粉虱(Dialeurodes citri);柑橘木虱(Diaphorina citri);白背盾蚧属(Diaspis spp.);草履介壳虫属(Drosicha spp.);西圆尾蚜属(Dysaphis spp.),例如Dysaphis apiifolia、车前圆尾蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphistulipae);灰粉蚧属(Dysmicoccus spp.);小绿叶蝉属(Empoasca spp.),例如Empoascaabrupta、马铃薯小绿叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、茄微叶蝉(Empoasca solana)、Empoasca stevensi;绵蚜属(Eriosoma spp.),例如Eriosomaamericanum、苹果绵蚜(Eriosoma lanigerum)、Eriosoma pyricola;斑叶蝉属(Erythroneura spp.);Eucalyptolyma spp.;褐木虱属(Euphyllura spp.);Euscelisbilobatus;弗氏粉蚧属(Ferrisia spp.);咖啡地粉蚧(Geococcus coffeae);Glycaspisspp.;银合欢木虱(Heteropsylla cubana)、颊木虱(Heteropsylla spinulosa);假桃病毒叶蝉(Homalodisca coagulata);桃大尾蚜(Hyalopterus arundinis),李大尾蚜(Hyalopterus pruni);吹绵蚧属(Icerya spp.),例如吹绵蚧(Icerya purchasi);片角叶蝉属(Idiocerus spp.);扁喙叶蝉属(Idioscopus spp.);灰飞虱(Laodelphaxstriatellus);蜡蚧属(Lecanium spp.),例如褐盔蜡蚧(Lecanium corni)(=Parthenolecanium corni);盾蚧属(Lepidosaphes spp.),例如榆蛎盾蚧(Lepidosaphesulmi);萝卜蚜(Lipaphis erysimi);斑衣蜡蝉(Lycorma delicatula);长管蚜属(Macrosiphum spp.),例如马铃薯长管蚜(Macrosiphum euphorbiae)、Macrosiphumlilii、蔷薇长管蚜(Macrosiphum rosae);二点叶蜂(Macrosteles facifrons);突眼长蝽属(Mahanarva spp.);高粱蚜(Melanaphis sacchari);Metcalfiella spp.;Metcalfapruinosa;麦无网蚜(Metopolophium dirhodum);黑缘平翅斑蚜(Monellia costalis);Monelliopsis pecanis;瘤蚜属(Myzus spp.),例如冬葱瘤蚜(Myzus ascalonicus)、李瘤蚜(Myzus cerasi)、Myzus ligustri、饰瘤蚜(Myzus ornatus)、桃蚜(Myzus persicae)、烟蚜(Myzus nicotianae);莴苣衲长管蚜(Nasonovia ribisnigri);黑尾叶蝉属(Nephotettix spp.),例如黑尾叶蝉(Nephotettix cincticeps)、二条斑黑尾叶蝉(Nephotettix nigropictus);稻褐飞虱(Nilaparvata lugens);Oncometopia spp.;Orthezia praelonga;中华稻蝗(Oxya chinensis);Pachypsylla spp.;杨梅缘粉虱(Parabemisia myricae);木虱属(Paratrioza spp.),例如马铃薯木虱(Paratriozacockerelli);片盾蚧属(Parlatoria spp.);瘿绵蚜属(Pemphigus spp.),例如囊柄瘿绵蚜(Pemphigus bursarius)、Pemphigus populivenae;玉米蜡蝉(Peregrinus maidis);绵粉蚧属(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(Phylloxeraspp.),例如Phylloxera devastatrix、Phylloxera notabilis;苏铁褐点并盾蚧(Pinnaspis aspidistrae);臀纹粉蚧属(Planococcus spp.),例如枯臀纹粉蚧(Planococcus citri);Prosopidopsylla flava;梨形原绵蚧(Protopulvinariapyriformis);桑白盾蚧(Pseudaulacaspis pentagona);粉蚧属(Pseudococcus spp.),例如嗜桔粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、长尾粉蚧(Pseudococcus longispinus)、真葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni);Psyllopsis spp.;木虱属(Psylla spp.),例如Psylla buxi、苹果木虱(Psylla mali)、梨木虱(Psylla pyri);金小蜂属(Pteromalus spp.);Pyrillaspp.;笠圆盾蚧属(Quadraspidiotus spp.),例如胡桃圆盾蚧(Quadraspidiotusjuglansregiae)、Quadraspidiotus ostreaeformis、梨圆盾蚧(Quadraspidiotusperniciosus);Quesada gigas;平刺粉蚧属(Rastrococcus spp.);缢管蚜属(Rhopalosiphum spp.),例如玉米蚜(Rhopalosiphum maidis)、Rhopalosiphumoxyacanthae、禾谷缢管蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphumrufiabdominale);黑盔蚧属(Saissetia spp.),例如咖啡黑盔蚧(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、橄榄黑盔蚧(Saissetia oleae);葡萄带叶蝉(Scaphoideus titanus);麦二叉蚜(Schizaphis graminum);苏铁刺圆盾蚧(Selenaspidusarticulatus);麦长管蚜(Sitobion avenae);长唇基飞虱属(Sogata spp.);白背飞虱(Sogatella furcifera);Sogatodes spp.;三角蝶(Stictocephala festina);树粉虱(Siphoninus phillyreae);Tenalaphara malayensis;Tetragonocephela spp.;美洲山核桃长斑蚜(Tinocallis caryaefoliae);广胸沫蝉属(Tomaspis spp.);声蚜属(Toxopteraspp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus);温室白粉虱(Trialeurodes vaporariorum);尖翅木虱属(Trioza spp.),例如Trioza diospyri;小叶蝉属(Typhlocyba spp.);尖盾蚧属(Unaspis spp.);葡萄根瘤虱(Viteus vitifolii);么叶蝉属(Zygina spp.);
异翅亚目(Heteroptera),例如,南瓜缘蝽(Anasa tristis);拟丽蝽属(Antestiopsis spp.);Boisea spp.;土长蝽属(Blissus spp.);俊盲蝽属(Calocorisspp.);斑腿微刺盲蝽(Campylomma livida);异背长蝽属(Cavelerius spp.);臭虫属(Cimex spp.),例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、蝠臭虫(Cimex pilosellus);白瓣麦寄蝇属(Collaria spp.);绿盲蝽(Creontiades dilutus);胡椒缘蝽(Dasynus piperis);Dichelops furcatus;厚氏长棒网蝽(Diconocoris hewetti);棉红蝽属(Dysdercus spp.);美洲蝽属(Euschistus spp.),例如Euschistus heros、褐美洲蝽(Euschistus servus)、Euschistus tristigmus、三点美洲蝽(Euschistus variolarius);扁盾蝽属(Eurygaster spp.);荼翅蝽(Halyomorphahalys);盲蝽属(Heliopeltis spp.);Horcias nobilellus;稻缘蝽属(Leptocorisaspp.);异稻缘蝽(Leptocorisa varicornis);Leptoglossus occidentalis;叶足缘蝽(Leptoglossus phyllopus);丽盲蝽属(Lygocoris spp.),例如原丽盲蝽(Lygocorispabulinus);草盲蝽属(Lygus spp.),例如灰豆草盲蝽(Lygus elisus)、豆荚草盲蝽(Lygushesperus)、牧草盲蝽(Lygus lineolaris);蔗黑长蝽(Macropes excavatus);金光绿盲蝽(Monalonion atratum);绿蝽属(Nezara spp.),例如稻绿蝽(Nezara viridula);稻蝽属(Oebalus spp.);方背皮蝽(Piesma quadrata);壁蝽属(Piezodorus spp.),例如Piezodorus guildinii;杂盲蝽属(Psallus spp.);Pseudacysta persea;长红猎蝽属(Rhodnius spp.);可可褐盲蝽(Sahlbergella singularis);Scaptocoris castanea;黑蝽属(Scotinophora spp.);梨冠网蝽(Stephanitis nashi);Tibraca属种;锥猎蝽属种(Triatoma spp.);
膜翅目(Hymenoptera),例如,顶切叶蚁属(Acromyrmex spp.);残青叶蜂属(Athalia spp.),例如芜菁叶蜂(Athalia rosae);美切叶蚁属(Atta spp.);松叶蜂属(Diprion spp.),例如类欧松叶蜂(Diprion similis);实叶蜂属(Hoplocampa spp.),例如樱实叶蜂(Hoplocampa cookei)、苹叶蜂(Hoplocampa testudinea);毛蚁属(Lasiusspp.);阿根廷蚁(Linepithema humile);小家蚁(Monomorium pharaonis);树蜂属(Sirexspp.);红火蚁(Solenopsis invicta);蚁属(Tapinoma spp.);大树蜂属(Urocerus spp.);胡蜂属(Vespa spp.),例如黄边胡蜂(Vespa crabro);黑树蜂属(Xeris spp.);
等足目(Isopoda),例如,鼠妇虫(Armadillidium vulgare)、栉水虱(Oniscusasellus)、球鼠妇(Porcellio scaber);
等翅目(Isoptera),例如,家白蚁属(Coptotermes spp.),例如台湾乳白蚁(Coptotermes formosanus);堆角白蚁(Cornitermes cumulans);堆砂白蚁属(Cryptotermes spp.);楹白蚁属(Incisitermes spp.);稻麦小白蚁(Microtermesobesi);土白蚁属(Odontotermes spp.);散白蚁属(Reticulitermes spp.),例如黄肢散白蚁(Reticulitermes flavipes)、西方散白蚁(Reticulitermes hesperus);
鳞翅目(Lepidoptera),例如,小蜡螟(Achroia grisella);桑剑纹夜蛾(Acronicta major);褐带卷蛾属(Adoxophyes spp.),例如棉褐带卷蛾(Adoxophyesorana);烦夜蛾(Aedia leucomelas);地老虎属(Agrotis spp.),例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon);波纹夜蛾属(Alabama spp.),例如棉叶波纹夜蛾(Alabama argillacea);脐橙螟蛾(Amyelois transitella);条麦蛾属(Anarsia spp.);干煞夜蛾属(Anticarsia spp.),例如大豆夜蛾(Anticarsia gemmatalis);条小卷蛾属(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(Busseolaspp.);卷叶蛾属(Cacoecia spp.);荼细蛾(Caloptilia theivora);烟卷蛾(Capuareticulana);苹果蠹蛾(Carpocapsa pomonella);桃柱果蛾(Carposina niponensis);冬天蛾(Cheimatobia brumata);禾草螟属(Chilo spp.),例如禾草螟(Chilo plejadellus)、二化螟(Chilo suppressalis);色卷蛾属(Choristoneura spp.);葡萄果蠹蛾(Clysiaambiguella);纵卷叶野螟属(Cnaphalocerus spp.);稻纵卷叶螟(Cnaphalocrocismedinalis);云卷蛾属(Cnephasia spp.);细蛾属(Conopomorpha spp.);球颈象属(Conotrachelus spp.);Copitarsia spp.;小卷蛾属(Cydia spp.),例如豌豆小卷蛾(Cydia nigricana)、苹果小卷蛾(Cydia pomonella);Dalaca noctuides;绢野螟属(Diaphania spp.);小蔗螟(Diatraea saccharalis);钻夜蛾属(Earias spp.);Ecdytolopha aurantium;南美玉米苗斑螟(Elasmopalpus lignosellus);非洲蔗螟(Eldana saccharina);粉斑螟属(Ephestia spp.),例如烟草粉螟(Ephestia elutella)、地中海粉螟(Ephestia kuehniella);叶小卷蛾属(Epinotia spp.);苹淡褐卷蛾(Epiphyaspostvittana);荚斑螟属(Etiella spp.);棕卷蛾属(Eulia spp.);女贞细卷蛾(Eupoecilia ambiguella);黄毒蛾属(Euproctis spp.),例如褐尾蠹(Euproctischrysorrhoea);切夜蛾属(Euxoa spp.);脏切夜蛾属(Feltia spp.);大蜡螟(Galleriamellonella);细蛾属(Gracillaria spp.);小食心虫属(Grapholitha spp.),例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholita prunivora);蚀叶野螟属(Hedylepta spp.);铃夜蛾属(Helicoverpa spp.),例如棉铃虫(Helicoverpa armigera)、玉米穗虫(Helicoverpa zea);实夜蛾属(Heliothis spp.),例如烟芽夜蛾(Heliothisvirescens);褐织蛾(Hofmannophila pseudospretella);同斑螟属(Homoeosoma spp.);长卷蛾属(Homona spp.);苹果巢蛾(Hyponomeuta padella);柿蒂虫(Kakivoriaflavofasciata);贪夜蛾属(Laphygma spp.);茄黄斑螟蛾(Leucinodes orbonalis);潜叶蛾属(Leucoptera spp.),例如咖啡潜叶蛾(Leucoptera coffeella);潜叶细蛾属(Lithocolletis spp.),例如苹果斑幕潜叶蛾(Lithocolletis blancardella);绿果冬夜蛾(Lithophane antennata);花翅小卷蛾属(Lobesia spp.),例如葡萄花翅小卷蛾(Lobesia botrana);白缘豆夜蛾(Loxagrotis albicosta);毒蛾属(Lymantria spp.),例如舞毒蛾(Lymantria dispar);潜蛾属(Lyonetia spp.),例如桃潜蛾(Lyonetiaclerkella);黄褐天幕毛虫(Malacosoma neustria);豆荚野螟(Maruca testulalis);甘蓝夜蛾(Mamestra brassicae);暮眼蝶(Melanitis leda);毛胫夜蛾属(Mocis spp.);Monopis obviella;东方粘虫(Mythimna separata);Nemapogon cloacellus;水螟属(Nymphula spp.);Oiketicus spp.;麦秆夜蛾属种(Oria spp.);瘤丛螟属(Orthagaspp.);秆野螟属(Ostrinia spp.),例如欧洲玉米螟(Ostrinia nubilalis);黑角负泥虫(Oulema melanopus)、稻负泥虫(Oulema oryzae);小眼夜蛾(Panolis flammea);稻弄蝶属(Parnara spp.);红铃麦蛾属(Pectinophora spp.),例如棉红铃虫(Pectinophoragossypiella);潜跳甲属(Perileucoptera spp.);块茎蛾属(Phthorimaea spp.),例如马铃薯块茎蛾(Phthorimaea operculella);桔潜蛾(Phyllocnistis citrella);小潜细蛾属(Phyllonorycter spp.),例如斑幕潜叶蛾(Phyllonorycter blancardella)、Phyllonorycter crataegella;粉蝶属(Pieris spp.),例如菜粉蝶(Pieris rapae);荷兰石竹小卷蛾(Platynota stultana);印度谷蛾(Plodia interpunctella);金翅夜蛾属(Plusia spp.);小菜蛾(Plutellaxylostella)(=Plutella maculipennis);小白巢蛾属(Prays spp.);斜纹夜蛾属(Prodenia spp.);烟草天蛾属(Protoparce spp.);粘虫属(Pseudaletia spp.),例如一星粘虫(Pseudaletia unipuncta);大豆尺夜蛾(Pseudoplusia includens);玉米螟(Pyrausta nubilalis);薄荷灰夜蛾(Rachiplusianu);禾螟属(Schoenobius spp.),例如三化螟(Schoenobius bipunctifer);白禾螟属(Scirpophaga spp.),例如稻白螟(Scirpophaga innotata);黄地老虎(Scotia segetum);蛀茎夜蛾属(Sesamia spp.),例如大螟(Sesamia inferens);长须卷蛾属(Sparganothisspp.);灰翅夜蛾属(Spodoptera spp.),例如Spodoptera eradiana、甜菜夜蛾(Spodopteraexigua)、草地贪夜蛾(Spodoptera frugiperda)、Spodoptera praefica;举肢蛾属(Stathmopoda spp.);花生麦蛾(Stomopteryx subsecivella);兴透翅蛾属(Synanthedonspp.);安笫斯马铃薯块茎蛾(Tecia solanivora);大显夜蛾(Thermesia gemmatalis);木塞谷蛾(Tinea cloacella)、袋谷蛾(Tinea pellionella);幕谷蛾(Tineolabisselliella);栎绿卷蛾属(Tortrix spp.);毛毡衣蛾(Trichophaga tapetzella);粉夜蛾属(Trichoplusia spp.),例如粉纹夜蛾(Trichoplusia ni);三化螟(Tryporyzaincertulas);番茄斑潜蝇(Tuta absoluta);灰蝶属(Virachola spp.);
直翅目(Orthoptera)或跳跃亚目(Saltatoria),例如,家蟋(Achetadomesticus);Dichroplus spp.;蝼蛄属(Gryllotalpa spp.),例如欧洲蝼蛄(Gryllotalpagryllotalpa);蔗蝗属(Hieroglyphus spp.);飞蝗属(Locusta spp.),例如东亚飞蝗(Locusta migratoria);黑蝗属(Melanoplus spp.),例如迁飞黑蝗(Melanoplusdevastator);Paratlanticus ussuriensis;沙漠蝗(Schistocerca gregaria);
虱目(Phthiraptera),例如,牛羽虱属(Damalinia spp.)、血虱属(Haematopinusspp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、Phylloera vastatrix、阴虱(Phthirus pubis)、嚼虱属(Trichodectes spp.);
啮虫目(Psocoptera),例如,粉啮虫属(Lepinotus spp.)、书虱属(Liposcelisspp.);
蚤目(Siphonaptera),例如,角叶蚤属(Ceratophyllus spp.);栉首蚤属(Ctenocephalides spp.),例如犬栉首蚤(Ctenocephalides canis)、猫栉头蚤(Ctenocephalides felis);扰蚤(Pulex irritans);穿皮潜蚤(Tunga penetrans);印鼠客蚤(Xenopsylla cheopsis);
缨翅目(Thysanoptera),例如,玉米黄呆蓟马(Anaphothrips obscurus);稻蓟马(Baliothrips biformis);鲜食葡萄镰蓟马(Drepanothrips reuteri);Enneothripsflavens;花蓟马属(Frankliniella spp.),例如烟褐花蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、东方花蓟马(Frankliniella tritici)、Frankliniella vaccinii、威廉期花蓟马(Frankliniellawilliamsi);阳蓟马属(Heliothrips spp.);温室条篱蓟马(Hercinothrips femoralis);葡萄蓟马(Rhipiphorothrips cruentatus);硬蓟马属(Scirtothrips spp.);Taeniothrips cardamomi;蓟马属(Thrips spp.),例如南黄蓟马(Thrips palmi)、葱蓟马(Thrips tabaci);
衣鱼目(Zygentoma)(=缨尾目(Thysanura)),例如,栉衣鱼属(Ctenolepismaspp.)、衣鱼(Lepisma saccharina)、盗火虫(Lepismodes inquilinus)、小灶衣鱼(Thermobia domestica);
综合纲(Symphyla),例如,么蚰属(Scutigerella spp.),例如白松虫(Scutigerella immaculata);
软体动物门(Mollusca),例如双壳纲(Bivalvia)的有害生物,例如,贻贝属(Dreissena spp.),
以及腹足纲(Gastropoda),例如,阿勇蛞蝓属(Arion spp.),例如黑蛞蝓(Arionater rufus);双脐螺属(Biomphalaria spp.);泡螺属(Bulinus spp.);野蛞蝓属(Deroceras spp.),例如光滑野蛞蝓(Deroceras laeve);土蜗属(Galba spp.);椎实螺属(Lymnaea spp.);钉螺属(Oncomelania spp.);福寿螺属(Pomacea spp.);琥珀螺属(Succinea spp.);
来自扁形动物门(Platyhlminthes)和线虫动物门(Nematoda)的动物寄生虫和人类寄生虫,例如,猫圆线虫属(Aelurostrongylus spp.)、裂口线虫属(Amidostomum spp.)、钩口线虫属(Ancylostoma spp.)、管圆线虫属(Angiostrongylus spp.)、异尖线虫属(Anisakis spp.)、裸头绦虫属(Anoplocephala spp.)、蛔虫属(Ascaris spp.)、鸡蛔虫属(Ascaridia spp.)、贝利蛔虫属(Baylisascaris spp.)、布鲁线虫属(Brugia spp.)、仰口线虫属(Bunostomum spp.)、毛细线虫属(Capillaria spp.)、夏柏特线虫属(Chabertiaspp.)、支睾吸虫属(Clonorchis spp.)、古柏线虫属(Cooperia spp.)、环体线虫属(Crenosoma spp.)、杯口属(Cyathostoma spp.)、双腔吸虫属(Dicrocoelium spp.)、网尾线虫属(Dictyocaulus spp.)、裂头绦虫属(Diphyllobothrium spp.)、复孔绦虫属(Dipylidium spp.)、恶丝虫属(Dirofilaria spp.)、龙线虫属(Dracunculus spp.)、棘球绦虫属(Echinococcus spp.)、棘口吸虫属(Echinostoma spp.)、蛲虫属(Enterobiusspp.)、真鞘属(Eucoleus spp.)、片形吸虫属(Fasciola spp.)、拟片形吸虫属(Fascioloides spp.)、姜片虫属(Fasciolopsis spp.)、类丝虫属(Filaroides spp.)、筒线属(Gongylonema spp.)、三代虫属(Gyrodactylus spp.)、丽线虫属(Habronema spp.)、血矛线虫属(Haemonchus spp.)、螺旋线虫属(Heligmosomoides spp.)、异刺线虫属(Heterakis spp.)、膜壳绦虫属(Hymenolepis spp.)、猪圆形属(Hyostrongylus spp.)、光丝虫属(Litomosoides spp.)、罗阿丝虫属(Loa spp.)、后圆线虫属(Metastrongylusspp.)、次睾吸虫属(Metorchis spp.)、中殖孔绦虫属(Mesocestoides spp.)、蒙尼茨绦虫属(Moniezia spp.)、缪勒线虫属(Muellerius spp.)、板口线虫属(Necator spp.)、细颈线虫属种(Nematodirus spp.)、日本圆线虫属(Nippostrongylus spp.)、结节线虫属(Oesophagostomum spp.)、沃鲁线虫属(Ollulanus spp.)、盘尾丝虫属(Onchocercaspp.)、后睾吸虫属(Opisthorchis spp.)、奥斯勒线虫属(Oslerus spp.)、胃线虫属(Ostertagia spp.)、尖尾线虫属(Oxyuris spp.)、Paracapillaria spp.、副丝虫属(Parafilaria spp.)、并殖吸虫属(Paragonimus spp.)、同端盘吸虫属(Paramphistomumspp.)、副裸头绦虫属(Paranoplocephala spp.)、副蛔虫属(Parascaris spp.)、栓尾线虫属(Passalurus spp.)、原圆线虫属(Protostrongylus spp.)、血吸虫属(Schistosomaspp.)、腹腔丝虫属(Setaria spp.)、旋毛线虫属(Spirocerca spp.)、冠丝虫属(Stephanofilaria spp.)、冠尾线属(Stephanurus spp.)、粪圆线虫属(Strongyloidesspp.)、圆线虫属(Strongylus spp.)、开口虫属(Syngamus spp.)、绦虫属(Taenia spp.)、背带线虫属(Teladorsagia spp.)、吸吮线虫属(Thelazia spp.)、弓蛔线虫属(Toxascarisspp.)、弓蛔虫属(Toxocara spp.)、毛线虫属(Trichinella spp.)、毛毕吸虫属(Trichobilharzia spp.)、毛圆线虫属(Trichostrongylus spp.)、鞭虫属(Trichurisspp.)、钩虫属(Uncinaria spp.)、吴策线虫属(Wuchereria spp.);
线虫动物门的植物有害生物,即植物寄生性线虫,尤其是野外垫刃属(Aglenchusspp.),例如居农野外垫刃线虫(Aglenchus agricola);蛇线虫属(Anguina spp.),例如小麦粒瘿线虫(Anguina tritici);滑刃线虫属(Aphelenchoides spp.),例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoides fragariae);刺线虫属(Belonolaimus spp.),例如细小刺线虫(Belonolaimus gracilis)、芹刺线虫(Belonolaimus longicaudatus)、Belonolaimus nortoni;伞滑刃线虫属(Bursaphelenchus spp.),例如椰子红环腐线虫(Bursaphelenchus cocophilus)、Bursaphelenchus eremus、松材线虫(Bursaphelenchus xylophilus);坏死线虫属(Cacopaurus spp.),例如胡桃线虫(Cacopaurus pestis);小环线虫属(Criconemellaspp.),例如弯曲小环线虫(Criconemella curvata)、Criconemella onoensis、装饰小环线虫(Criconemella ornata)、畸形小环线虫(Criconemella rusium)、异盘中环线虫(Criconemella xenoplax)(=Mesocriconema xenoplax);轮线虫属(Criconemoidesspp.),例如Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum;茎线虫属(Ditylenchus spp.),例如鳞球茎茎线虫(Ditylenchus dipsaci);锥线虫属(Dolichodorus spp.);球异皮线虫属(Globodera spp.),例如马铃薯白线虫(Globoderapallida)、马铃薯金线虫(Globodera rostochiensis);螺旋线虫属(Helicotylenchusspp.),例如双宫螺旋线虫(Helicotylenchus dihystera);半轮线虫属(Hemicriconemoides spp.);鞘线虫属(Hemicycliophora spp.);异皮线虫属(Heteroderaspp.),例如燕麦异皮线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜异皮线虫(Heterodera schachtii);纽带线虫属(Hoplolaimus spp.);长针线虫属(Longidorus spp.),例如非洲长针线虫(Longidorus africanus);根结线虫属(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(Meloidogyneincognita);瓢线虫属(Meloinema spp.);珍珠线虫属(Nacobbus spp.);拟茎线虫属(Neotylenchus spp.);拟滑刃线虫(Paraphelenchus spp.);拟毛刺线虫属(Paratrichodorus spp.),例如微小拟毛刺线虫(Paratrichodorus minor);短体线虫属(Pratylenchus spp.),例如穿刺短体线虫(Pratylenchus penetrans);Pseudohalenchusspp.;平滑垫刃属(Psilenchus spp.);斑皮胞囊线虫属(Punctodera spp.);五沟线虫属种(Quinisulcius spp.);穿孔线虫属(Radopholus spp.),例如柑橘穿孔线虫(Radopholuscitrophilus)、香蕉穿孔线虫(Radopholus similis);肾状线虫属(Rotylenchulus spp.);盘旋线虫属(Rotylenchus spp.);盾线虫属(Scutellonema spp.);亚蛇形线虫属(Subanguina spp.);毛刺线虫属(Trichodorus spp.),例如Trichodorus obtusus;原始毛刺线虫(Trichodorus primitivus);矮化线虫属(Tylenchorhynchus spp.),例如饰环矮化线虫(Tylenchorhynchus annulatus);垫刃线虫属(Tylenchulus spp.),例如半穿刺线虫(Tylenchulus semipenetrans);剑线虫属种(Xiphinema spp.),例如剑线虫(Xiphinemaindex)。
此外,还可以防治原生动物(Protozoa)亚界、球虫目(Coccidia)例如艾美球虫属(Eimeria spp.)的有害生物。
式(I)化合物还可任选地以特定浓度或施用率用作除草剂、安全剂、生长调节剂或用于改进植物特性的试剂,用作杀微生物剂或杀配子剂,例如用作杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括抗类病毒的试剂)或用作抗MLO(类支原体生物体)和RLO(类立克次氏体生物体)的试剂。如果合适,它们还可用作合成其他活性化合物的中间体或前体。
制剂
本发明还涉及包含至少一种式(I)化合物的作为农药的制剂和由其制备的使用形式,例如浸液、滴液和喷液。在一些情况下,所述使用形式还包含农药和/或改善活性的佐剂,如渗透剂,例如植物油,例如油菜籽油、葵花籽油,矿物油,例如石蜡油,植物脂肪酸的烷基酯,例如油菜籽油甲酯或大豆油甲酯,或烷醇烷氧基化物;和/或展着剂(spreader),例如烷基硅氧烷和/或盐类,例如有机或无机铵盐或鳞盐,例如硫酸铵或磷酸氢二铵;和/或保持促进剂,例如磺基琥珀酸二辛酯或羟丙基瓜儿胶聚合物;和/或保湿剂,例如甘油;和/或肥料,例如含铵、含钾或含磷的肥料。
常规制剂为例如水溶性液体剂(SL)、乳液浓缩剂(EC)、水包乳剂(EW)、悬浮浓缩剂(SC、SE、FS、OD)、水分散粒剂(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例如由Crop Life International记载,以及记载于Pesticide Specifications、Manual on development and use of FAO and WHO specifications for pesticides、FAO Plant Production and Protection Papers-173(由FAO/WHO关于PesticideSpecifications的联合会议制订,2004,ISBN:9251048576)。所述制剂除包含一种或多种式(I)化合物以外,还任选地包含其他农业化学活性化合物。
优选地,这些制剂或使用形式包含助剂,例如增量剂、溶剂、自发性促进剂、载体、乳化剂、分散剂、防霜剂、杀生物剂、增稠剂和/或其他助剂,例如佐剂。在本文中,佐剂为一种增强制剂的生物学作用而其本身不具有任何生物学作用的组分。佐剂的实例为促进保持、铺展、附着到叶子表面或渗透的试剂。
这些制剂以已知的方式制备,例如通过将式(I)化合物与助剂如增量剂、溶剂和/或固体载体和/或其他助剂例如表面活性剂相混合。所述制剂在合适的设施中制备,或在施用之前或施用过程中制备。
所使用的助剂可为适合于将特定特性如特定物理、技术和/或生物学特性赋予式(I)化合物的制剂或由这些制剂制得的使用形式(例如即用型农药,如喷液或拌种产品)的物质。
合适的增量剂为例如水、极性和非极性有机化学液体,例如选自以下种类:芳族和非芳族烃(如石蜡、烷基苯、烷基萘、氯苯)、醇和多元醇(如果合适,其也可被取代、醚化和/或酯化)、酮(如丙酮、环己酮)、酯(包括脂肪和油)和(聚)醚、未取代和取代的胺、酰胺、内酰胺(如N-烷基吡咯烷酮)和内酯、砜和亚砜(如二甲基亚砜)。
如果所使用的增量剂为水,则还可使用例如有机溶剂作为助溶剂。基本上,合适的液体溶剂为:芳族化合物,如二甲苯、甲苯或烷基萘;氯代芳族烃或氯化脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷或石蜡,例如矿物油馏分;矿物油和植物油;醇,如丁醇或乙二醇以及它们的醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基甲酰胺和二甲基亚砜;以及水。
原则上,可以使用所有合适的溶剂。合适的溶剂的实例为芳族烃,如二甲苯、甲苯或烷基萘;氯代芳族烃或氯代脂族烃,如氯苯、氯乙烯或二氯甲烷;脂族烃,如环己烷、石蜡、石油馏分;矿物油和植物油;醇,如甲醇、乙醇、异丙醇、丁醇或乙二醇,以及它们的醚和酯;酮,如丙酮、甲基乙基酮、甲基异丁基酮或环己酮;强极性溶剂,如二甲基亚砜;以及水。
原则上,可以使用所有合适的载体。可用的载体尤其包括:例如,铵盐和粉碎的天然矿物质如高岭土、粘土、滑石、白垩、石英、绿坡缕石、蒙脱石或硅藻土,以及粉碎的合成材料如细碎的二氧化硅、氧化铝和天然或合成的硅酸盐、树脂、蜡和/或固体肥料。同样可使用这些载体的混合物。用于颗粒剂的有用载体包括:例如压碎并分级的天然岩石,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,以及有机材料如锯屑、纸、椰壳、玉米穗轴和烟草秆的颗粒。
还可使用液化的气态增量剂或溶剂。特别合适的增量剂或载体为在环境温度和大气压力下为气态的那些,例如气溶胶推进剂气体,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为聚丙烯酸盐;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的缩聚物、与取代的酚(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;以及含有硫酸根、磺酸根和磷酸根的化合物的衍生物,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、蛋白质水解产物、木素亚硫酸盐废液和甲基纤维素。如果式(I)的化合物之一和/或惰性载体之一不溶于水并且当在水中进行施用时,则表面活性剂的存在是有利的。
可以使用着色剂作为制剂及源自其的使用形式中的其他助剂,所述着色剂例如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料如茜素染料、偶氮染料和金属酞菁染料;以及营养素和痕量营养素如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐以及锌盐。
其他的组分可为稳定剂,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。
增粘剂也可作为其他助剂存在于制剂和源自其的使用形式中,所述增粘剂例如羧甲基纤维素以及粉末、颗粒或胶乳形式的天然和合成聚合物(如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯),或天然磷脂如脑磷脂和卵磷脂和合成磷脂。其他可能的助剂为矿物油和植物油。
任选地,所述制剂和源自其的使用形式中可存在其他助剂。这些添加剂的实例包括香料、保护胶体、粘合剂、胶粘剂、增稠剂、触变剂、渗透剂、保持促进剂、稳定剂、螯合剂(sequestrants)、络合剂、保湿剂、展着剂。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所有那些降低动态表面张力的物质,例如磺基琥珀酸二辛酯,或提高粘弹性的物质,例如羟丙基瓜尔胶聚合物。
在本文中,合适的渗透剂为所有那些常用于促进农业化学活性化合物向植物渗透的物质。在本文中,渗透剂通过其从(通常为水性的)施用液体和/或从喷雾涂层渗入植物的表皮从而增加活性化合物在表皮中移动性的能力来定义。可使用文献(Baur等,1997,Pesticide Science 51,131-152)中记载的方法测定此特性。实例包括:醇烷氧基化物,如椰子脂肪乙氧基化物(10)或异十三烷基乙氧基化物(12);脂肪酸酯,例如油菜籽油甲酯或大豆油甲酯;脂肪胺烷氧基化物,例如牛脂胺乙氧基化物(15);或铵盐和/或鳞盐,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)化合物,或特别优选0.01重量%至95重量%的式(I)化合物,更优选0.5重量%至90重量%的式(I)化合物,基于所述制剂的重量计。
由所述制剂制备的使用形式(特别是农药)中式(I)化合物的含量可在宽范围内变化。所述使用形式中式(I)化合物的浓度通常为0.00000001重量%至95重量%的式(I)化合物,优选0.00001重量%至1重量%,基于使用形式的重量计。所述化合物以适合于使用形式的常规方式使用。
混合物
式(I)化合物还可作为与以下一种或多种合适的物质的混合物来使用:杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀虫剂、微生物制品(microbiologicals)、有益物种(beneficial species)、除草剂、肥料、鸟驱避剂、植物增强剂(phytotonics)、止繁殖剂、安全剂、信息化学物质和/或植物生长调节剂,从而由此例如拓宽作用谱、延长作用时间、增加作用速率、防止排斥或防止抗性的发展。此外,这些活性化合物的组合物可改善植物生长和/或提高对非生物因子,例如高温或低温、对干旱或对高水量或土壤盐度的耐受性。还可以改善开花和结果的性能、优化发芽能力和根发育、促进采收并提高产量、影响成熟、提高采收产品的品质和/或营养价值、延长采收产品的储存寿命和/或提高其可加工性。
此外,式(I)化合物可以与其他活性化合物或信息化学物质如引诱剂和/或鸟驱避剂和/或植物激活剂和/或生长调节剂和/或肥料的混合物的形式存在。同样,式(I)化合物可用于改善植物特性例如采收材料的生长、产量和品质。
在本发明的一个具体实施方案中,式(I)化合物以与其他化合物——优选下文所述的化合物——的混合物的制剂或由这些制剂制备的使用形式而存在。
如果下述化合物中的某种化合物可以不同互变异构形式存在,那么这些形式也包括在内,即使在每种情况下没有明确提及。
杀虫剂/杀螨剂/杀线虫剂:
本文中以其通用名称说明的活性化合物是已知的并记载于例如农药手册(“ThePesticide Mannual”,笫16版,British Crop Protection Concil 2012)中或可在互联网(例如http://www.alanwood.net/pesticides)上搜索到。
(1)乙酰胆碱酯酶(AChE)抑制剂,例如,氨基甲酸酯类,例如棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、胺甲萘(carbaryl)、虫螨威(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)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、XMC和灭杀威(xylylcarb);或有机磷酸酯类,例如乙酰甲胺磷(acephate)、甲基吡恶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、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/DDVP(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、imicyafos、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯、异恶唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、砜吸磷(oxydemeton-methyl)、对硫磷甲酯(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀硫磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、肟硫磷(phoxim)、甲基嘧啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基嘧啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)和蚜灭磷(vamidothion)。
(2)GABA门控氯化物通道拮抗剂类,例如环戊二烯有机氯类,例如氯丹(chlordane)和硫丹(endosulfan);或苯基吡唑类(fiproles),例如乙虫腈(ethiprole)和氟虫腈(fipronil)。
(3)钠通道调节剂/电压门控钠通道阻断剂,例如,拟除虫菊酯类,例如氟丙菊酯(acrinathrin)、丙烯除虫菊酯(allethrin)、d-顺-反烯丙菊酯、d-反烯丙菊酯、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(bioallethrin s-cyclopentenyl isomer)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfiuthrin)、p-氟氯氰菊酯、氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯、γ-氯氟氰菊酯、氯氰菊酯(cypermethrin)、α-氯氰菊酯、β-氯氰菊酯、θ-氯氰菊酯、ζ-氯氰菊酯、苯醚氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-transisomers)、溴氰菊酯(deltamethrin)、右旋烯炔菊酯[(EZ)-(1R)异构体](empenthrin[(EZ)-(1R)isomers)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻恩菊酯(kadethrin)、苄氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans isomer)、炔烯菊酯(prallethrin)、除虫菊素(pyrethrins)(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]、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin);或DDT;或甲氧氯(methoxychlor)。
(4)烟碱乙酰胆碱受体(nAChR)激动剂类,例如新烟碱类(neonicotinoids),例如啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam);或烟碱(nicotine);或氟啶虫胺腈(sulfoxaflor)。
(5)烟碱乙酰胆碱受体(nAChR)变构激活剂,例如多杀霉素类(spinosyns),例如乙基多杀菌素(spinetoram)和多杀菌素(spinosad)。
(6)氯离子通道激活剂类,例如阿凡曼菌素类(avermectins)/米尔倍霉素类(milbemycins),例如阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectinbenzoate)、雷皮菌素(lepimectin)和弥拜菌素(milbemectin)。
(7)保幼激素模拟物,例如保幼激素类似物类,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
卤代烷,例如溴甲烷和其他卤代烷;或氯化苦(chloropicrine);或硫酰氟(sulfuryl fluoride);或硼砂;或吐酒石。
(9)选择性拒食素,例如吡蚜酮(pymetrozine);或氟啶虫酰胺(flonicamid)。
(10)螨生长抑制剂类,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)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis),以及BT植物蛋白:Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb、Cry34/35Ab1。
(12)氧化磷酸化抑制剂类,ATP干扰剂类,例如丁醚脲(diafenthiuron);或有机锡化合物,例如三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatin oxide);或炔螨特(propargite);或四氯杀螨砜(tetradifon)。
(13)通过中断H质子梯度而起作用的氧化磷酸化解偶联剂类,例如虫螨腈(chlorfenapyr)、二硝甲酚(DNOC)和氟虫胺(sulfluramid)。
(14)烟碱乙酰胆碱受体拮抗剂类,例如杀虫磺(bensultap)、杀螟丹盐酸盐(cartap hydrochloride)、杀虫环(thiocylam)和杀虫双(thiosultap-sodium)。
(15)几丁质生物合成抑制剂类,0型,例如双三氟虫脲(bistrifluron)、定虫隆(chlofluazuron)、除虫脲(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、虱螨脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、伏虫脲(teflubenzuron)和杀铃脲(triflumuron)。
(16)几丁质生物合成抑制剂类,1型,例如噻嗪酮(buprofezin)。
(17)蜕皮抑制剂类(特别用于双翅目,即双翅类昆虫),例如,灭蝇胺(cyromazine)。
(18)蜕皮激素受体激动剂类,例如环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)。
(19)章鱼胺能激动剂类,例如双甲脒(amitraz)。
(20)复合物-III型电子传递抑制剂类,例如氟蚁腙(hydramethylnone);或灭螨醌(acequinocyl);或嘧螨酯(fluacrypyrim)。
(21)复合物-I型电子传递抑制剂类,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(Derris))。
(22)电压门控钠通道阻断剂类,例如茚虫威(indoxacarb)或氰氟虫腙(metaflumizone)。
(23)乙酰基-CoA羧化酶的抑制剂类,例如特窗酸(tetronic acid)和特特拉姆酸(tetramic acid)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型电子传递抑制剂类,例如膦类,例如磷化铝、磷化钙、膦和磷化锌;或氰化物。
(25)复合物-II型电子传递抑制剂类,例如腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen)。
(28)鱼尼丁(ryanodine)受体效应剂(effector)类,例如二酰胺类,例如氯虫苯甲酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)和氟虫双酰胺(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)、丁烯氟虫腈(flufiprole)、氟吡菌酰胺(fluopyram)、氟吡呋喃酮(flupyradifurone)、呋喃虫酰肼(fufenozide)、heptafluthrin、氯噻啉(imidaclothiz)、异菌脲(iprodione)、氯氟醚菊酯(meperfluthrin)、哌虫啶(paichongding)、pyflubumide、pyrifluquinazon、嘧螨胺(pyriminostrobin)、四氟醚菊酯(tetramethylfluthrin)和碘甲烷;以及此外基于坚强芽孢杆菌(Bacillus firmus)(I-1582,BioNeem,Votivo)的制品,以及下列化合物: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(由WO2005/077934获知)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(由WO2006/043635获知)、{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(由WO2003/106457获知)、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(由WO2006/003494获知)、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(由WO2009/049851获知)、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(由WO2009/049851获知)、4-(丁-2-炔-1基氧基)-6-(3,5-二甲基哌啶-1-基)-5-氟嘧啶(由WO2004/099160获知)、4-(丁-2-炔-1-基氧基)-6-(3-氯苯基)嘧啶(由WO2003/076415获知)、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(由WO2005/085216获知)、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(由WO2009/002809获知)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氯-3-甲基苯甲酰基]-2-甲基肼甲酸甲酯(由WO2005/085216获知)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氰基-3-甲基苯甲酰基]-2-乙基肼甲酸甲酯(由WO2005/085216获知)、2-[2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)-5-氰基-3-甲基苯甲酰基]-2-甲基肼甲酸甲酯(由WO2005/085216获知)、2-[3,5-二溴-2-({[3-溴-1-(3-氯吡啶-2-基)-1H-吡唑-5-基]羰基}氨基)苯甲酰基]-2-乙基肼甲酸甲酯(由WO2005/085216获知)、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(由WO2010/069502获知)、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(由CN102057925获知)、3-氯-N-(2-氰基丙-2-基)-N-[4-(1,1,1,2,3,3,3-七氟丙-2-基)-2-甲基苯基]酞酰胺(由WO2012/034472获知)、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(由WO2010/129500获知)、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-氧代硫杂环丁烷基-3-基)苯甲酰胺(由WO2009/080250获知)、N-[(2E)-1-[(6-氯吡啶-3-基)甲基]吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(由WO2012/029672获知)、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(由WO2009/099929获知)、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(由WO2009/099929获知)、(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(由WO2010/069266获知)、(2E)-1-[(6-氯吡啶-3-基)甲基]-N′-硝基-2-亚戊基肼甲脒(由WO2010/060231获知)、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(由CN101337940获知)、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(由WO2008/134969获知)。
杀真菌剂
本文中以其通用名称说明的活性化合物是已知的并记载于例如“农药手册”中或互联网(例如:http://www.alanwood.net/pesticides)上。
(1)麦角固醇生物合成抑制剂,例如(1.1)aldimorph、(1.2)戊环唑(azaconazole)、(1.3)联苯三唑醇(bitertanol)、(1.4)糠菌唑(bromuconazole)、(1.5)环丙唑醇(cyproconazole)、(1.6)苄氯三唑醇(diclobutrazole)、(1.7)苯醚甲环唑(difenoconazole)、(1.8)烯唑醇(diniconazole)、(1.9)M-烯唑醇(diniconazole-M)、(1.10)十二环吗啉(dodemorph)、(1.11)十二环吗啉乙酸盐(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)氟喹唑(fluquinconazole)、(1.20)呋嘧醇(flurprimidol)、(1.21)氟硅唑(flusilazole)、(1.22)粉唑醇(flutriafol)、(1.23)呋菌唑(furconazole)、(1.24)顺呋醚唑(furconazole-cis)、(1.25)己唑醇(hexaconazole)、(1.26)抑霉唑(imazalil)、(1.27)抑霉唑硫酸盐(imazalilsulphate)、(1.28)亚胺唑(imibenconazole)、(1.29)种菌唑(ipconazole)、(1.30)叶菌唑(metconazole)、(1.31)腈菌唑(myclobutanil)、(1.32)萘替芬(naftifin)、(1.33)氟苯嘧啶醇(nuarimol)、(1.34)恶咪唑(oxpoconazole)、(1.35)多效唑(paclobutrazole)、(1.36)稻瘟酯(pefurazoate)、(1.37)戊菌唑(penconazole)、(1.38)粉病灵(piperalin)、(1.39)咪鲜胺(prochloraz)、(1.40)丙环唑(propiconazole)、(1.41)丙硫菌唑(prothioconazole)、(1.42)稗草丹(pyributicarb)、(1.43)啶斑肟(pyrifenox)、(1.44)唑喹菌酮(quinconazole)、(1.45)硅氟唑(simeconazole)、(1.46)螺环菌胺(spiroxamine)、(1.47)戊唑醇(tebuconazole)、(1.48)特比萘芬(terbinafin)、(1.49)氟醚唑(tetraconazole)、(1.50)三唑酮(triadimefon)、(1.51)三唑醇(triadimenol)、(1.52)十三吗啉(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)烯效唑-p(uniconazole-p)、(1.58)烯霜苄唑(viniconazole)、(1.59)伏立康唑(voriconazole)、(1.60)1-(4-氯苯基)-2-(1H-1,2,4-三唑-1-基)环庚醇、(1.61)1-(2,2-二甲基-2,3-二氢-1H-茚-1-基)-1H-咪唑-5-甲酸甲酯、(1.62)N′-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基甲脒、(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}甲脒和(1.64)O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]-1H-咪唑-1-硫代甲酸酯、(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)氟嘧菌胺(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(isopyrazam)顺式差向异构外消旋体1RS,4SR,9RS与反式差向异构外消旋体1RS,4SR,9SR的混合物、(2.12)吡唑萘菌胺(反式差向异构外消旋体)、(2.13)吡唑萘菌胺(反式差向异构对映异构体1R,4S,9S)、(2.14)吡唑萘菌胺(反式差向异构对映异构体1S,4R,9R)、(2.15)吡唑萘菌胺(顺式差向异构外消旋体1RS,4SR,9RS)、(2.16)吡唑萘菌胺(顺式差向异构对映异构体1R,4S,9R)、(2.17)吡唑萘菌胺(顺式差向异构对映异构体1S,4R,9S)、(2.18)灭锈胺(mepronil)、(2.19)氧化萎锈灵(oxycarboxin)、(2.20)氟唑菌苯胺(penflufen)、(2.21)吡噻菌胺(penthiopyrad)、(2.22)氟唑环菌胺(sedaxane)、(2.23)噻氟菌胺(thifluzamide)、(2.24)1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(2.25)3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、(2.26)3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、(2.27)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.28)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.29)苯并烯氟菌唑(benzovindiflupyr)、(2.30)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-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-桥亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.32)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.33)1,3,5-三甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.34)1-甲基-3-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.35)1-甲基-3-(三氟甲基)-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.36)1-甲基-3-(三氟甲基)-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.37)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.38)3-(二氟甲基)-1-甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.39)1,3,5-三甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.40)1,3,5-三甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.41)麦锈灵(benodanil)、(2.42)2-氯-N-(1,1,3-三甲基-2,3-二氢-iH-茚-4-基)吡啶-3-甲酰胺、(2.43)isofetamid。
(3)作用于呼吸链复合物III的呼吸抑制剂(呼吸链抑制剂),例如(3.1)唑嘧菌胺(ametoctradin)、(3.2)吲唑磺菌胺(amisulbrom)、(3.3)腈嘧菌酯(azoxystrobin)、(3.4)氰霜唑(cyazofamid)、(3.5)甲香菌酯(coumethoxystrobin)、(3.6)丁香菌酯(coumoxystrobin)、(3.5)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)醚菌酯(kresoxim-methyl)、(3.14)苯氧菌胺(metominostrobin)、(3.15)肟醚菌胺(orysastrobin)、(3.16)啶氧菌酯(picoxystrobin)、(3.17)唑菌胺酯(pyraclostrobin)、(3.18)唑胺菌酯(pyrametostrobin)、(3.19)唑胺菌酯(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-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-(甲酰基氨基)-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)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)噻苯哒唑(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]嘧啶和(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)波尔多混合液、(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、(5.7)氧化铜、(5.8)氯氧化铜(copper oxychloride)、(5.9)硫酸铜、(5.10)苯氟磺胺(dichlofluanid)、(5.11)二氰蒽醌(dithianon)、(5.12)多果定(dodine)、(5.13)多果定游离碱(dodine free base)、(5.14)福美铁(ferbam)、(5.15)氟灭菌丹(fluorfolpet)、(5.16)灭菌丹(folpet)、(5.17)双胍辛盐(guazatine)、(5.18)双胍辛乙酸盐(guazatine acetate)、(5.19)双胍辛胺(iminoctadine)、(5.20)双胍辛烷基苯磺酸盐(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(zinc metiram)、(5.27)喹啉铜(copper-oxine)、(5.28)丙烷脒(propamidine)、(5.29)丙森锌(propineb)、(5.30)硫和硫制品,例如,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)、(7.2)杀稻瘟菌素-S(blasticidin-S)、(7.3)嘧菌环胺(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)喹啉以及(7.9)氧四环素(oxytetracycline)和(7.10)链霉素(streptomycin)。
(8)ATP产生抑制剂,例如,(8.1)三苯基乙酸锡(fentin acetate)、(8.2)三苯基氯化锡(fentin chloride)、(8.3)毒菌锡(fentin hydroxide)和(8.4)硅噻菌胺(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)异丙菌胺(iprovalicarb)、(9.5)双炔酰菌胺(mandipropamid)、(9.6)多抗霉素(polyoxins)、(9.7)多氧霉素(polyoxorim)、(9.8)有效霉素A(validamycin A)、(9.9)缬菌胺(valifenalate)和(9.10)多抗霉素B(polyoxinB)。
(10)脂质和膜合成抑制剂,例如(10.1)联苯、(10.2)氯苯甲醚(chloroneb)、(10.3)氯硝胺(dicloran)、(10.4)敌瘟磷(edifenphos)、(10.5)土菌灵(etridiazole)、(10.6)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)硫菌威(prothiocarb)、(10.12)吡菌磷(pyrazophos)、(10.13)五氯硝苯(quintozene)、(10.14)四氯硝基苯(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)环丙酰菌胺(carpropamid)、(11.2)双氯氰菌胺(diclocymet)、(11.3)氰菌胺(fenoxanil)、(11.4)四氯苯酞(fthalide)、(11.5)咯喹酮(pyroquilon)、(11.6)三环唑(tricyclazole)和(11.7)2,2,2-三氟乙基{3-甲基-1-[(4-甲基苯甲酰基)氨基]丁-2-基}氨基甲酸酯。
(12)核酸合成抑制剂,例如(12.1)苯霜灵(benalaxyl)、(12.2)精苯霜灵(benalaxyl-M(kiralaxyl))、(12.3)乙嘧酚磺酸酯(bupirimate)、(12.4)clozylacon、(12.5)二甲嘧酚(dimethirimol)、(12.6)乙嘧酚(ethirimol)、(12.7)呋霜灵(furalaxyl)、(12.8)恶霉灵(hymexazole)、(12.9)甲霜灵(metalaxyl)、(12.10)高效甲霜灵(metalaxyl-M)(精甲霜灵(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)解偶联剂,例如(14.1)乐杀螨(binapacryl)、(14.2)消螨普(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)bethoxazin、(15.3)卡巴西霉素(capsimycin)、(15.4)香芹酮(carvone)、(15.5)灭螨猛(chinomethionat)、(15.6)pyriofenone)(chlazafenone)、(15.7)硫杂灵(cufraneb)、(15.8)环氟菌胺(cyflufenamid)、(15.9)霜脲氰(cymoxanil)、(15.10)啶酰菌胺(cyprosulfamide)、(15.11)棉隆(dazomet)、(15.12)咪菌威(debacarb)、(15.13)双氯酚(dichlorophen)、(15.14)哒菌清(diclomezine)、(15.15)野燕枯(difenzoquat)、(15.16)野燕枯甲基硫酸酯(difenzoquat metilsulphate)、(15.17)二苯胺(diphenylamine)、(15.18)EcoMate、(15.19)胺苯吡菌酮(fenpyrazamine)、(15.20)氟酰菌胺(flumetover)、(15.21)fluorimid、(15.22)磺菌胺(flusulfamide)、(15.23)flutianil、(15.24)三乙膦酸铝(fosetyl-aluminium)、(15.25)三乙膦酸钙(fosetyl-calcium)、(15.26)三乙膦酸钠(fosetyl-sodium)、(15.27)六氯苯(hexachlorobenzene)、(15.28)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)米多霉素(mildiomycin)、(15.33)纳他霉素(natamycin)、(15.34)二甲基二硫代氨基甲酸镍(nickel dimethyldithiocarbamate)、(15.35)酞菌酯(nitrothal-isopropyl)、(15.36)辛噻酮(octhilinone)、(15.37)oxamocarb、(15.38)oxyfenthiin、(15.39)五氯苯酚(pentachlorophenol)及其盐、(15.40)苯醚菊酯(phenothrin)、(15.41)磷酸及其盐、(15.42)霜霉威乙膦酸盐(propamocarb-fosetylate)、(15.43)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)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-1,5-二氧杂环壬-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-2-基1H-咪唑-1-甲酸酯、(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]二噻英并[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-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-苯基苯酚和盐、(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-甲基甲脒、(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-甲基甲脒、(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-甲酸、(15.92)喹啉-8-醇、(15.93)喹啉-8-醇硫酸酯(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)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(15.129)5-(烯丙基硫基)-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-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l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-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-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-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-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-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-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-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-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、(15.150)3-(二氟甲基)-N-甲氧基-1-甲基-N-[1-(2,4,6-三氯苯基)丙-2-基]-1H-吡唑-4-甲酰胺、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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-甲基甲脒、(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。(1)至(15)类中所提及的所有混合组分任选地与合适的碱或酸形成盐,如果它们能够基于其官能团形成盐的话。
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、植物提取物和由微生物形成的产物,包括蛋白质和次级代谢产物。
生物农药包括细菌,如产芽孢细菌、根部定殖细菌和起生物杀虫剂、杀真菌剂或杀线虫剂作用的细菌。
用作或可用作生物农药的这类细菌的实例为:
解淀粉芽孢杆菌(Bacillus amyloliquefaciens),菌株FZB42(DSM 231179);或蜡样芽孢杆菌(Bacillus cereus),特别是蜡样芽孢杆菌菌株CNCM I-1562;或坚强芽孢杆菌(Bacillus firmus),菌株1-1582(登录号(Accession Number)CNCM I-1582);或短小芽孢杆菌(Bacillus pumilus),特别是菌株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),特别是菌株GB03(登记号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);苏芸金芽孢杆菌(Bacillus thuringiensis),特别是苏云金芽孢杆菌以色列亚种(B.thuringiensis subspecies israelensis)(血清型H-14),菌株AM65-52(登录号ATCC 1276),或苏云金芽胞杆菌鲇泽亚种(B.thuringiensis subsp.aizawai),特别是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌库尔斯塔克亚种(B.thuringiensissubsp.kurstaki)菌株HD-1,或苏云金芽孢杆菌拟步行甲亚种(B.thuringiensissubsp.tenebrionis)菌株NB 176(SD-5428);穿刺巴斯德芽菌(Pasteuria penetrans),巴斯德氏芽菌属(Pasteuria spp.)(肾形肾状线虫(Rotylenchulus reniformisnematode))-PR3(登录号ATCC SD-5834);细黄链霉菌(Streptomyces microflavus)菌株AQ6121(=QRD 31.013,NRRL B-50550);鲜黄链霉菌(Streptomyces galbus)菌株AQ 6047(登录号NRRL 30232)。
用作或可用作生物农药的真菌和酵母的实例为:
球孢白僵菌(Beauveria bassiana),特别是菌株ATCC 74040;盾壳霉(Coniothyrium minitans),特别是菌株CON/M/91-8(登录号DSM-9660);轮枝孢属(Lecanicillium spp.),特别是菌株HRO LEC 12,蜡蚧轮枝菌(Lecanicilliumlecanii),(以前称为Verticilliumlecanii),特别是菌株KV01;金龟子绿僵菌(Metarhiziumanisopliae),特别是菌株F52(DSM3884/ATCC 90448);核果梅奇酵母菌(Metschnikowiafructicola),特别是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现名:Isaria fumosorosea),特别是菌株IFPC 200613或菌株Apopka 97(登录号ATCC20874);淡紫色拟青霉(Paecilomyces lilacinus),特别是淡紫色拟青霉菌株251(AGAL89/030550);黄蓝状菌(Talaromyces flavus),特别是菌株V117b;深绿木霉(Trichodermaatroviride),特别是菌株SC1(登录号CBS 122089);哈茨木霉(Trichoderma harzianum),特别是哈茨木霉(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)(夏季水果卷叶蛾(summer fruit tortrix))颗粒体病毒(GV)、苹果蠹蛾(Cydia pomonella(codling moth))颗粒体病毒(GV)、棉铃虫(Helicoverpa armigera(cotton bollworm))核型多角体病毒(NPV)、甜菜夜蛾(Spodoptera exigua(beet armyworm))mNPV、草地贪夜蛾(Spodoptera frugiperda(fallarmyworm))mNPV、海灰翅夜蛾(Spodoptera littoralis(非洲棉树叶虫(African cottonleafworm)))NPV。
还包括作为“接种菌”加入至植物或植物部位或植物器官并通过其特定的性质来促进植物生长和植物键康的细菌和真菌。可提及的实例为:
土壤杆菌属(Agrobacterium spp.);茎瘤固氮根瘤菌(Azorhizobiumcaulinodans);固氮螺菌属(Azospirillum spp.);固氮菌属(Azotobacter spp.);慢生根瘤菌属(Bradyrhizobium spp.);伯霍尔德菌属(Burkholderia spp.),特别是洋葱伯霍尔德菌(Burkholderia cepacia)(以前称为洋葱假单胞菌(Pseudomonas cepacia));巨孢囊霉属(Gigaspora spp.),或Gigaspora monosporum;球囊霉属(Glomus spp.);蜡蘑属(Laccaria spp.);布氏乳杆菌(Lactobacillus buchneri);类球囊霉属(Paraglomusspp.);豆包菌(Pisolithus tinctorus);假单胞菌属(Pseudomonas spp.);根瘤菌属(Rhizobium spp.),尤其是三叶草根瘤菌(Rhizobium trifolii);须腹菌属(Rhizopogonspp.);硬皮锈菌属(Scleroderma spp.);乳牛肝菌属(Suillus spp.);链霉菌属(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白质和次级代谢产物)的实例为:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、Chenopodiumanthelminticum、几丁质(chitin)、Armour-Zen、欧洲鳞毛蕨(Dryopteris filix-mas)、问荆(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(奎奴亚藜皂苷(Chenopodiumquinoa saponin)提取物);除虫菊/除虫菊酯类(Pyrethrins/Pyrethrins)、苏里南苦木(Quassia amara);栎属(Quercus);皂树(Quillaja);Regalia;“RequiemTM Insecticide”;鱼藤酮(rotenone);鱼尼丁(ryania)/兰尼碱(ryanodine);聚合草(Symphytumofficinale);菊蒿(Tanacetumvulgare);百里香酚(thymol);Triact 70;TriCon;旱金莲(Tropaeulum majus);大荨麻(Urtica dioica);藜芦碱(Veratrin);白果槲寄生(Viscumalbum);十字花科(Brassicaceae)提取物,尤其是油菜粉末或芥末粉。
作为混合组分的安全剂
式(I)化合物可与安全剂结合,所述安全剂例如解草嗪(benoxacor)、喹氧乙酸(解草酯)(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(乙酯)(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalicanhydride)、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(CAS 129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS71526-07-3)、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
所有的植物和植物部位均可根据本发明进行处理。在本文中,植物应理解为意指所有的植物和植物部位,例如想要的和不想要的野生植物或作物植物(包括天然存在的作物植物),例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、番茄、豌豆和其他蔬菜物种、棉花、烟草、油菜以及果实植物(具有以下果实:苹果、梨、柑橘类果实和葡萄)。作物植物可为可通过常规育种和优化方法、或通过生物技术和基因工程法、或通过这些方法的结合而获得的植物,包括转基因植物且包括可受和不可受品种产权保护的植物品种。植物部位应理解为意指植物的地上和地下的所有部位和器官,如芽、叶、花及根,实例为叶、针叶、茎、干、花、子实体、果实和种子,以及块茎、根及地下茎。植物部位还包括采收材料、以及无性与有性繁殖材料,例如秧苗、块茎、根茎、插条和种子。
根据本发明用式(I)化合物对植物和植物部位进行的处理为直接进行的或通过常规处理方法使所述化合物作用于其周围、环境或贮存空间而进行,所述常规处理方法例如浸渍、喷洒、蒸发、喷雾(fogging)、散布(scattering)、涂抹、注入,以及在繁殖材料的情况下,特别是种子的情况下,还可通过施用一层或多层包衣进行。
如上所提及,可根据本发明处理所有植物及其部位。在一个优选的实施方案中,处理野生植物种和植物栽培种,或那些通过常规生物育种方法如杂交或原生质体融合而得到的植物物种,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——如果合适的话可与常规方法相结合——而得到的转基因植物和植物栽培种(基因修饰的有机体)及其部位。术语“部位”、“植物的部位”和“植物部位”已在上文作出解释。特别优选使用本发明来处理相应的市售的常规栽培种的植物或使用中的植物。植物栽培种理解为意指具有新特性(“性状”)的并且其已通过常规育种、诱变或重组DNA技术获得的植物。这些植物可以是栽培种、变种、生物型或基因型。
转基因植物、种子处理和整合事件
根据本发明优选处理的转基因植物或植物栽培种(通过基因工程而获得)包括通过基因修饰而接受了将特别有利的有用的特性(“性状”)赋予这些植物的基因材料的所有植物。这些特性的实例为:更好的植物生长、对高温或低温的提高的耐受性、对干旱或对水或土壤盐度水平的提高的耐受性、提高的开花性能、更容易采收、加速成熟、采收产品的更高的产量、更高的品质和/或更高的营养价值、采收产品的更好的贮存期和/或可加工性。这些特性的其他的和特别强调的实例为:植物对动物有害生物和微生物有害生物的提高的抵抗力,例如对昆虫、蛛形纲动物、线虫、螨虫、蛞蝓和蜗牛的抵抗力,其归因于例如在植物中形成的毒素、特别是通过苏云金芽孢杆菌的基因材料(例如通过基因CryIA(a)、CryIA(b)、CryIA(c)、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF,及其组合)在植物中形成的毒素;以及植物对植物病原性真菌、细菌和/或病毒提高的抵抗力,其归因于例如系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子(elicitor)以及抗性基因和相应地表达的蛋白质和毒素;以及植物对特定活性除草化合物的提高的耐受性,例如对咪唑啉酮、磺酰脲、草甘膦或草丁膦(phosphinothricin)(例如“PAT”基因)。赋予了所讨论的所需性状的基因也可在转基因植物中以相互结合的方式存在。可提及的转基因植物的实例为重要的作物植物,例如谷物(小麦、水稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、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(具有以下果实:苹果、梨、柑橘类果实和葡萄),特别强调的是玉米、大豆、小麦、水稻、马铃薯、棉花、甘蔗、烟草和油菜。特别强调的性状为植物对昆虫、蛛形纲动物、线虫以及蛞蝓和蜗牛的提高的抵抗力。
作物保护——处理类型
使用式(I)化合物对植物和植物部位的处理是直接进行的或通过使用常规处理方法作用于其环境、生境或储存空间而进行的,例如通过浸渍、喷洒、喷雾、灌溉、蒸发、撒粉、雾化、撒播、发泡、涂抹、撒布(spreading-on)、注入、浇水(浇灌)、滴灌,以及在繁殖材料,特别是种子的情况下,还以作为用于干燥种子处理的粉末、用于液体种子的处理的溶液、用于浆液处理的水溶性粉末,通过结壳(incrusting),通过用一层或多层包衣包覆等进行处理。此外,还可以通过超低容量法施用式(I)的化合物,或将所述施用形式或式(I)化合物本身注入到土壤中。
一种优选的对植物的直接处理是叶面施用,即将式(I)化合物施用于叶面上,其中处理频率和施用率应当根据所讨论的有害生物的侵染水平来调整。
在系统活性化合物的情况下,式(I)化合物也可通过根系统进入植物。然后,通过使式(I)化合物作用于植物的生境来处理该植物。这可以例如通过以下方式来完成:浇灌;或者通过混入土壤或营养液中,即,植物的位点(例如土壤或水培体系)被液体形式的式(I)化合物浸渍;或通过土壤施用,即,将本发明的式(I)化合物以固体形式(例如以颗粒剂的形式)引入至植物的位点。在水稻作物的情况下,其也可通过将式(I)化合物以固体施用形式(例如以颗粒剂的形式)计量加入到淹没的(flooded)水稻田来完成。
种子处理
通过处理植物的种子来防治动物有害生物是早就已知的,并且是持续改进的主题。然而,种子处理牵涉一系列的始终无法以令人满意的方式解决的问题。因此,期望开发用于保护种子和发芽植物的方法,该方法不需要或至少显著地降低在储存过程中、播种后或植物出苗后额外施用农药。此外,期望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保护,使其免受动物有害生物的侵害,而所使用的活性化合物则不会损害植物本身。特别地,为了以使用最少量的农药来实现对种子和发芽植物的最佳保护,用于处理种子的方法还应考虑抵抗或耐受有害生物的转基因植物的固有的杀虫或杀线虫的特性。
因此,本发明还特别涉及通过用式(I)化合物之一处理种子来保护种子和发芽植物免受有害生物侵害的方法。本发明的用于保护种子和发芽植物免受有害生物侵害的方法还包括在一次操作中同时地或依序地用式(I)的化合物和混合组分处理种子的方法。其还包括在不同时间用式(I)化合物和混合组分处理种子的方法。
本发明还涉及式(I)化合物用于处理种子以保护种子和所得植物免受动物有害物侵害的用途。
此外,本发明涉及已用本发明的式(I)化合物处理过以保护其免受动物有害生物侵害的种子。本发明还涉及已用式(I)化合物和混合组分同时处理过的种子。本发明还涉及已用式(I)化合物和混合组分在不同时间处理过的种子。在已用式(I)化合物和混合组分在不同时间处理过的种子的情况下,各物质可存在于该种子的不同层上。在这种情况下,包含式(I)化合物和混合组分的层可任选地被中间层隔开。本发明还涉及这样的种子:其中已经施用了式(I)化合物和混合组分作为包衣的组分或作为除包衣之外的其他一层或其他几层。
此外,本发明还涉及这样的种子:其在用式(I)化合物处理之后,对其进行涂膜过程以防止该种子遭受灰尘磨损。
系统性作用的式(I)化合物的优点之一在于,通过处理种子,不仅保护种子本身而且还保护由其所得的植物在出苗后免受动物有害生物的侵害。以此方式,可无需在播种时或其后不久对作物立即进行处理。
必需考虑的另一优点是,通过用式(I)化合物处理种子,可促进经处理过的种子的发芽和出苗。
同样被认为有利的是,式(I)化合物也可特别地用于转基因种子。
此外,式(I)化合物可与信号技术组合物或化合物结合使用,从而使得通过共生体例如根瘤菌、菌根/或植物内生细菌或真菌的定植更好,和/或优化固氮作用。
式(I)化合物适合于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。具体而言,其表现为以下的种子的形式:谷物(例如,小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、水稻、马铃薯、向日葵、咖啡、烟草、加拿大油菜(canola)、油菜、甜菜(例如,糖用甜菜和饲用甜菜)、花生、蔬菜(例如番茄、黄瓜、豆、十字花科蔬菜、洋葱和莴苣)、果实植物、草坪和观赏植物的种子。特别重要的是处理谷物(如小麦、大麦、黑麦和燕麦)、玉米、大豆、棉花、加拿大油菜、油菜和水稻的种子。
如上所提及,用式(I)化合物处理转基因种子也是特别重要的。其表现为通常包含至少一种控制特别是具有杀虫和/或杀线虫特性的多肽的表达的异源基因的植物的种子的形式。转基因种子中的异源基因可源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)、棒状杆菌属(Clavibacter)、球囊霉属(Glomus)或者粘帚霉属(Gliocladium)。本发明特别适于处理包含至少一种源自芽孢杆菌属(Bacillus sp)的异源基因的转基因种子。所述异源基因特别优选源自苏云金芽孢杆菌。
在本发明的上下文中,将式(I)化合物施用于种子。优选在种子足够稳定以避免在处理过程中发生损害的状态下处理种子。通常,可在采收和播种之间的任何时间点处理种子。通常使用的种子已从植物中分离并且已除去穗轴、外壳、茎、英、毛或果肉。例如,可以使用已采收、清理且干燥至允许储存的含水量的种子。或者,也可使用在干燥后用例如水处理然后再干燥(例如灌注(priming))的种子。如果是水稻的种子,也可以使用已经例如在水中浸泡至稻胚的某一阶段(“鸡胸阶段(pigeon breast stage)阶段”)的种子,从而刺激发芽和更均匀的出苗。
当处理种子时,通常必须注意对施用于种子的式(I)化合物的量和/或其他添加剂的量的选择为,使种子的发芽不会受到不利影响,或所得的植物不会受到损害。对于在某些施用率下可表现出植物毒性效应的活性化合物,必须特别确保这一点。
通常,将式(I)的化合物以合适的制剂形式施用至种子。用于种子处理的合适的制剂和方法对于本领域技术人员是已知的。
可将式(I)化合物转化成常规拌种制剂,如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂或其他种子包衣组合物,以及ULV制剂。
这些制剂以已知方式通过将式(I)化合物与常规添加剂混合而制备,所述常规添加剂,例如,常规增量剂以及溶剂或稀释剂、着色剂、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、胶粘剂、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着色剂为常规用于此目的的所有着色剂。可使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿剂为促进润湿且常规用于活性农业化学化合物的制剂的所有物质。优选使用烷基萘磺酸盐,如二异丙基萘磺酸盐或二异丁基萘磺酸盐。
可存在于可根据本发明使用的拌种制剂中的有用的分散剂和/或乳化剂为常规用于活性农业化学成分的制剂的所有非离子、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地包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基酚聚乙二醇醚,及其磷酸化或硫酸化衍生物。合适的阴离子分散剂尤其为木素磺酸盐、聚丙烯酸盐和芳基磺酸盐/甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为常规用于活性农业化学成分的制剂的所有抑制泡沫的物质。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业化学组合物中可用于此目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为在农业化学组合物中可用于此目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细碎的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的胶粘剂包括可用于拌种产品中的所有常规粘合剂。可优选提及的实例为聚乙烯吡咯烷酮、聚乙酸乙烯基酯、聚乙烯醇和甲基纤维素(tylose)。
可存在于可根据本发明使用的拌种制剂中的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。赤霉素是已知的(参见R.Wegler“Chemie derPflanzenschutz-und gsmittel”,第2卷,Springer Verlag,1970,笫401-412页)。
可根据本发明使用的拌种制剂可以直接或在预先用水稀释后用于处理各种不同种类的种子。例如,可使用浓缩剂或可通过用水稀释而由其获得的制剂来对以下种子进行拌种:谷物如小麦、大麦、黑麦、燕麦和黑小麦的种子,以及玉米、水稻、油菜、豌豆、豆、棉花、向日葵、大豆和甜菜的种子,或各种不同的蔬菜种子。可根据本发明使用的拌种制剂或其稀释的使用形式也可用于转基因植物的拌种。
对于用可根据本发明使用的拌种制剂或通过添加水而由其制得的使用形式处理种子而言,常规的用于拌种的所有混合单元都是有用的。具体而言,拌种的过程是:将种子以分批操作或连续操作的方式置于混合器内,加入特定的需要量的拌种制剂(以其本身或预先用水稀释后),然后将所有物质混合直到制剂均匀地分布在种子上。如果合适,之后进行干燥操作。
可根据本发明使用的拌种制剂的施用率可在相对宽的范围内变化。施用率取决于制剂中的式(I)化合物的具体含量和种子。式(I)化合物的施用率通常为0.001至50g/kg种子,优选0.01至15g/kg种子。
动物健康
在动物健康领域,即在兽医领域,式(I)化合物对于动物寄生虫、特别是外寄生虫或内寄生虫具有活性。术语内寄生虫特别包括蠕虫和原生动物,如球虫目(coccidia)。外寄生虫通常且优选为节肢动物,特别是昆虫和螨类。
在兽医领域,具有有利的恒温动物毒性的式(I)化合物适合于防治在畜禽养殖和畜牧业中,在家畜中、在养殖动物、动物园动物、实验室动物、实验动物和家养动物中出现的寄生虫。它们对寄生虫的所有发育阶段或特定发育阶段均具有活性。
农业家畜包括,例如,哺乳动物,如绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿,以及特别是牛和猪;或家禽,如火鸡、鸭、鹅,以及特别是鸡;鱼或甲壳动物,例如在水产养殖中;以及昆虫,如蜜蜂。
家养动物包括,例如,哺乳动物,如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,以及特别是狗、猫、笼鸟、爬行动物、两栖动物和观赏鱼。
根据一个优选实施方案,将式(I)化合物给药于哺乳动物。
根据另一个优选实施方案,将式(I)化合物给药于鸟类,即笼鸟,以及特别是家禽。
通过使用式(I)化合物防治动物寄生虫旨在减少或预防疾病、死亡和性能降低(在肉、奶、羊毛、皮、蛋、蜜等的情况下),从而使得动物饲养更经济、更简单,并可实现更好的动物健康状态。
本文中使用的关于动物健康领域的术语“防治(control或controlling)”意指式(I)化合物有效地将各寄生虫在被这类寄生虫感染的动物中的发病率降低至无害水平。更具体而言,本文中使用的“防治”意指式(I)化合物有效地杀死各寄生虫、抑制其生长或抑制其增殖方面。
节肢动物包括:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、颚虱属(Linognathusspp.)、人虱属(Pediculus spp.)、阴虱属(Phtirus spp.)、管虱属(Solenopotes spp.);食毛目(Mallophagida)和钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属(Trimenopon spp.)、禽虱属(Menopon spp.)、巨羽虱属(Trinoton spp.)、牛羽虱属(Bovicola spp.)、Werneckiella spp.、Lepikentron spp.、畜虱属(Damalina spp.)、啮毛虱属(Trichodectes spp.)、猫羽虱属(Felicola spp.);双翅目(Diptera)和长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、库蚊属(Culex spp.)、蚋属(Simulium spp.)、真蚋属(Eusimuliumspp.)、白蛉属(Phlebotomus spp.)、罗蛉属(Lutzomyia spp.)、库蠓属(Culicoidesspp.)、斑虻属(Chrysops spp.)、短蚋亚属(Odagmia spp.)、维蚋亚属(Wilhelmia spp.)、瘤虻属(Hybomitra spp.)、黄虻属(Atylotus spp.)、虻属(Tabanus spp.)、麻虻属(Haematopota spp.)、Philipomyia spp.、蜂虱蝇属(Braula spp.)、家蝇属(Musca spp.)、齿股蝇属(Hydrotaea spp.)、螫蝇属(Stomoxys spp.)、黑角蝇属(Haematobia spp.)、莫蝇属(Morellia spp.)、厕蝇属(Fannia spp.)、舌蝇属(Glossina spp.)、丽蝇属(Calliphoraspp.)、绿蝇属(Lucilia spp.)、金蝇属(Chrysomyia spp.)、污蝇属(Wohlfahrtia spp.)、麻蝇属(Sarcophaga spp.)、狂蝇属(Oestrus spp.)、皮蝇属(Hypoderma spp.)、胃蝇属(Gasterophilus spp.)、虱蝇属(Hippobosca spp.)、羊虱蝇属(Lipoptena spp.)、蜱蝇属(Melophagus spp.)、鼻狂蝇属(Rhinoestrus spp.)、大蚊属(Tipula spp.);蚤目(Siphonapterida),例如蚤属(Pulex spp.)、栉头蚤属(Ctenocephalides spp.)、潜蚤属(Tunga spp.)、客蚤属(Xenopsylla spp.)、角叶蚤属(Ceratophyllus spp.);
异翅亚目(Heteropterida),例如臭虫属(Cimex spp.)、锥猎蝽属(Triatomaspp.)、红猎蝽属(Rhodnius spp.)、大锥蝽属(Panstrongylus spp.);以及蜚蠊目(Blattarida)的公害有害生物和卫生有害生物。
节肢动物还包括:
蜱螨亚纲(Acari)(蜱螨目(Acarina))和后气门目(Metastigmata),例如软蜱科(argasidae),如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、残喙蜱属(Otobius spp.);硬蜱科(Ixodidae),如硬蜱属(Ixodes spp.)、花蜱属(Amblyomma spp.)、扇头蜱属(牛蜱属)(Rhipicephalus(Boophilus)spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemophysalis spp.)、璃眼蜱属(Hyalomma spp.)、扇头蜱属(Rhipicephalus spp.)(多宿主蜱的原属);中气门目(mesostigmata),如皮刺螨属(Dermanyssus spp.)、禽刺螨属(Ornithonyssus spp.)、肺刺螨属(Pneumonyssus spp.)、刺利螨属(Raillietia spp.)、肺刺螨属(Pneumonyssus spp.)、胸刺螨属(Sternostoma spp.)、蜂螨属(Varroa spp.)、蜂盾螨属(Acarapis spp.);辐螨目(Actinedida)(前气门亚目(Prostigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、禽螯螨属(Ornithocheyletia spp.)、肉螨属(Myobia spp.)、疮螨属(Psorergates spp.)、蠕形螨属(Demodex spp.)、恙螨属(Trombicula spp.)、Neotrombiculla spp.、Listrophorus spp.;和粉螨目(Acaridida)(无气门亚目(Astigmata)),例如粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、颈下螨属(Hypodectes spp.)、翅螨属(Pterolichus spp.)、痒螨属(Psoroptes spp.)、皮螨属(Chorioptes spp.)、耳疥螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、背肛螨属(Notoedres spp.)、鸟疥螨属(Knemidocoptes spp.)、气囊螨属(Cytodites spp.)、鸡雏螨属(Laminosioptes spp.)。
寄生性原生动物包括:
鞭毛纲(鞭毛虫纲)(Mastigophora(Flagellata)),例如锥虫科(Trypanosomatidae),例如,布氏锥虫(Trypanosoma b.brucei)、布氏冈比亚锥虫(T.b.gambiense)、布氏罗德西亚锥虫(T.b.rhodesiense)、刚果锥虫(T.congolense)、克氏锥虫(T.cruzi)、伊氏锥虫(T.evansi)、马锥虫(T.equinum)、路氏锥虫(T.lewisi)、鲈鱼锥虫(T.percae)、猿猴锥虫(T.simiae)、活跃锥虫(T.vivax)、巴西利什曼原虫(Leishmaniabrasiliensis)、杜氏利什曼原虫(L.donovani)、热带利什曼原虫(L.tropica),例如毛滴虫科(Trichomonadidae),例如兰伯贾笫虫(Giardia lamblia)、犬贾笫虫(G.canis);
肉鞭虫门(Sarcomastigophora)(根足总纲(Rhizopoda)),如内阿米巴科(Entamoebidae),例如,痢疾内阿米巴(Entamoeba histolytica);Hartmanellidae,例如,棘阿米巴属(Acanthamoeba sp.)、Harmanella sp.;
顶复门(Apicomplexa)(孢子虫纲(Sporozoa))如艾美球虫科(Eimeridae),例如,堆形艾美球虫(Eimeria acervulina)、E.adenoides、阿拉巴马艾美球虫(E.alabamensis)、鸭艾美球虫(E.anatis)、鹅艾美球虫(E.anserina)、阿氏艾美球虫(E.arloingi)、阿沙塔艾美球虫(E.ashata)、奥博伦艾美球虫(E.auburnensis)、牛艾美球虫(E.bovis)、布氏艾美球虫(E.brunetti)、犬艾美球虫(E.canis)、E.chinchillae、E.clupearum、鸽艾美球虫(E.columbae)、E.contorta、克兰多尔氏艾美球虫(E.crandalis)、狄氏艾美球虫(E.debliecki)、分散艾美球虫(E.dispersa)、E.ellipsoidales、镰刀形艾美球虫(E.falciformis)、福氏艾美球虫(E.faurei)、黄色艾美球虫(E.flavescens)、加洛帕沃尼艾美球虫(E.gallopavonis)、哈氏艾美球虫(E.hagani)、肠艾美球虫(E.intestinalis)、E.iroquoina、无残艾美球虫(E.irresidua)、唇艾美球虫(E.labbeana)、E.leucarti、大型艾美球虫(E.magna)、巨型艾美球虫(E.maxima)、中型艾美球虫(E.media)、珠鸡艾美球虫(E.meleagridis)、珠鸡和缓米堤艾美球虫(E.meleagrimitis)、和缓艾美球虫(E.mitis)、毒害艾美球虫(E.necatrix)、雅氏艾美球虫(E.ninakohlyakimovae)、羊艾美球虫(E.ovis)、小型艾美球虫(E.parva)、孔雀艾美球虫(E.pavonis)、穿孔艾美球虫(E.perforans)、E.phasani、梨形艾美球虫(E.piriformis)、早熟艾美球虫(E.praecox)、E.residua、粗糙艾美球虫(E.scabra)、艾美球虫属种(E.spec.)、斯氏艾美球虫(E.stiedai)、猪艾美球虫(E.suis)、禽艾美球虫(E.tenella)、树艾美球虫(E.truncata)、特鲁特艾美球虫(E.truttae)、朱氏艾美球虫(E.zuernii)、球虫属(Globidium spec.),贝氏等孢子球虫(Isospora belli)、犬等孢子球虫(I.canis)、猫等孢子球虫(I.felis)、俄亥俄等孢子球虫(I.ohioensis)、芮氏等孢子球虫(I.rivolta)、等孢子球虫属(I.spec.)、猪等孢子球虫(I.suis)、Cystisospora spec.、隐孢子虫属(Cryptosporidium spec.),特别是微小隐孢子虫(C.parvum);如弓形虫科(Toxoplasmadidae),例如鼠弓形虫(Toxoplasmagondii)、Hammondia heydornii、犬新孢子虫(Neospora caninum)、Besnoitia besnoitii;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)、S.ovicanis、S.ovifelis、S.neurona、肉孢子虫属(S.spec.)、猪人肉孢子虫(S.suihominis),如Leucozoidae,例如Leucozytozoon simondi,如疟原虫科(Plasmodiidae),例如伯氏疟原虫(Plasmodium berghei)、P.falciparum、P.malariae、卵形疟原虫(P.ovale)、间日疟原虫(P.vivax),疟原虫属(P.spec.),如梨质纲(Piroplasmea),例如阿根廷巴贝虫(Babesia argentina)、牛巴贝虫(B.bovis)、B.canis、巴贝虫属(B.spec.)、小泰勒虫(Theileria parva),泰勒虫属(Theileria spec.),如匿虫亚目(Adeleina),例如犬肝簇虫(Hepatozoon canis)、肝簇虫属(H.spec.)。
病原性内寄生虫,其为蠕虫,包括扁形动物门(Platyhelmintha)(例如单殖亚纲(Monogenea)、绦虫(cestode)和吸虫(Trematode))、线虫类、棘头虫纲(Acanthocephala)和舌形虫属(Pentastoma),包括:
单殖亚纲:例如:三代虫属(Gyrodactylus spp.)、指环虫属(Dactylogyrusspp.)、多盘吸虫属(Polystoma spp.);
绦虫:假叶目(Pseudophyllidea),例如:裂头属(Diphyllobothrium spp.)、迭宫绦虫属(Spirometra spp.)、Schistocephalus spp.、舌状绦虫属(Ligula spp.)、Bothridium spp.、复殖孔绦虫属(Diplogonoporus spp.);
圆叶目(Cyclophyllidea),例如:中殖孔绦虫属(Mesocestoides spp.)、裸头绦虫属(Anoplocephala spp.)、副裸头绦虫属(Paranoplocehala spp.)、蒙尼茨绦虫属(Moniezia spp.)、繸体绦虫属(Thysanosomsa spp.)、曲子宫绦虫属(Thysaniezia spp.)、无卵黄腺绦虫属(Avitellina spp.)、Stilesia spp.、鸣绦虫属(Cittotaenia spp.)、Andyra spp.、伯特绦虫属(Bertiella spp.)、带绦虫属(Taenia spp.)、棘球绦虫属(Echinococcus spp.)、泡尾绦虫属(Hydatigera spp.)、代凡绦虫属(Davainea spp.)、瑞利绦虫属(Raillietina spp.)、膜壳绦虫属(Hymenolepis spp.)、棘鳞绦虫属(Echinolepis spp.)、Echinocotyle spp.、双睾绦虫属(Diorchis spp.)、复孔绦虫属(Dipylidium spp.)、约优克斯绦虫属(Joyeuxiella spp.)、复孔绦虫属(Diplopylidiumspp.);
吸虫:复殖亚纲(Digenea),例如:双穴吸虫属(Diplostomum spp.)、茎双穴吸虫属(Posthodiplostomum spp.)、血吸虫属(Schistosoma spp.)、毛毕吸虫属(Trichobilharzia spp.)、鸟毕吸虫属(Ornithobilharzia spp.)、澳毕吸虫属(Austrobilharzia spp.)、巨毕吸虫属(Gigantobilharzia spp.)、彩蚴吸虫属(Leucochloridium spp.)、短咽吸虫属(Brachylaima spp.)、棘口吸虫属(Echinostomaspp.)、棘缘吸虫属(Echinoparyphium spp.)、棘隙吸虫属(Echinochasmus spp.)、Hypoderaeum spp.、片形吸虫属(Fasciola spp.)、Fascioloides spp.、姜片吸虫属(Fasciolopsis spp.)、环腔吸虫属(Cyclocoelum spp.)、盲腔吸虫属(Typhlocoelumspp.)、同端盘吸虫属(Paramphistomum spp.)、杯殖吸虫属(Calicophoron spp.)、殖盘吸虫属(Cotylophoron spp.)、巨盘吸虫属(Gigantoctyle spp.)、Fischoederius spp.、Gastrothylacus spp.)背孔吸虫属(Notocotylus spp.)、下弯吸虫属(Catatropis spp.)、斜睾吸虫属(Plagiorchis spp.)、前殖吸虫属(Prosthogonimus spp.)、双腔吸虫属(Dicrocoelium spp.)、阔盘吸虫属(Eurytema spp.)、隐孔吸虫属(Troglotrema spp.)、并殖吸虫属(Paragonimus spp.)、表孔吸虫属(Collyriclum spp.)、侏形吸虫属(Nanophyetus spp.)、后睾吸虫属(Opisthorchis spp.)、支睾吸虫属(Clonorchis spp.)、次睾吸虫属(Metorchis spp.)、异形吸虫属(Heterophyes spp.)、后殖吸虫属(Metagonimus spp.);
线虫:毛形科(Trichinellida),例如:鞭虫属(Trichuris spp.)、毛细线虫属(Capillaria spp.)、Paracapillaria spp.、真鞘属(Eucoleus spp.)、Trichomosoidesspp.、毛线虫属(Trichinella spp.);
垫刃目(Tylenchida),例如:细丝鲶属(Micronema spp.)、类圆线虫属(Strongyloides spp.)。
杆形亚目(Rhabditina),例如:圆线虫属(Strongylus spp.)、三齿属(Triodontophorus spp.)、食道齿属(Oesophagodontus spp.)、毛线属(Trichonemaspp.)、辐首线虫属(Gyalocephalus spp.)、柱咽属(Cylindropharynx spp.)、杯口线虫属(Poteriostomum spp.)、Cyclococercus spp.、杯冠属(Cylicostephanus spp.)、结节线虫属(Oesophagostomum spp.)、夏柏特线虫属(Chabertia spp.)、冠尾线属(Stephanurusspp.)、钩口线虫属(Ancylostoma spp.)、钩虫属(Uncinaria spp.)、板口线虫属(Necatorspp.)、仰口线虫属(Bunostomum spp.)、球头线虫属(Globocephalus spp.)、开口虫属(Syngamus spp.)、杯口属(Cyathostoma spp.)、后圆线虫属(Metastrongylus spp.)、网尾线虫属(Dictyocaulus spp.)、缪勒线虫属(Muellerius spp.)、原圆线虫属(Protostrongylus spp.)、新圆线虫属种(Neostrongylus spp.)、囊尾线虫属(Cystocaulus spp.)、肺圆属(Pneumostrongylus spp.)、Spicocaulus spp.、麂圆线虫属(Elaphostrongylus spp.)、拟马鹿圆线虫属(Parelaphostrongylus spp.)、环体线虫属(Crenosoma spp.)、Paracrenosoma spp.、Oslerus spp.、管圆线虫属(Angiostrongylusspp.)、猫圆线虫属(Aelurostrongylus spp.)、类丝虫属(Filaroides spp.)、副类丝虫属(Parafilaroides spp.)、毛圆线虫属(Trichostrongylus spp.)、血矛线虫属(Haemonchusspp.)、胃线虫属(Ostertagia spp.)、背带线虫属(Teladorsagia spp.)、马歇尔线虫属(Marshallagia spp.)、古柏线虫属(Cooperia spp.)、日圆线虫属(Nippostrongylusspp.)、Heligmosomoides spp.、细颈线虫属(Nematodirus spp.)、猪圆线虫属(Hyostrongylus spp.)、尖柱线虫属(Obeliscoides spp.)、裂口线虫属(Amidostomumspp.)、沃鲁线虫属(Ollulanus spp.);
旋尾目(Spirurida),例如:尖尾线虫属(Oxyuris spp.)、蛲虫属(Enterobiusspp.)、栓尾线虫属(Passalurus spp.)、管状线虫属(Syphacia spp.)、无刺线虫属(Aspiculuris spp.)、异刺线虫属(Heterakis spp.);蛔虫属(Ascaris spp.)、弓蛔线虫属(Toxascaris spp.)、弓蛔虫属(Toxocara spp.)、贝利蛔线虫属(Baylisascaris spp.)、副蛔虫属(Parascaris spp.)、异尖线虫属(Anisakis spp.)、鸡蛔虫属(Ascaridia spp.);颚口线虫属(Gnathostoma spp.)、泡翼线虫属(Physaloptera spp.)、吸吮线虫属(Thelaziaspp.)、筒线虫属(Gongylonema spp.)、丽线虫属(Habronema spp.)、Parabronema spp.、德拉西线虫属(Draschia spp.)、龙线虫属(Dracunculus spp.);冠丝虫属(Stephanofilariaspp.)、副丝虫属(Parafilaria spp.)、腹腔丝虫属(Setaria spp.)、罗阿丝虫属(Loaspp.)、恶丝虫属(Dirofilaria spp.)、光丝虫属(Litomosoides spp.)、布鲁线虫属(Brugia spp.)、吴策线虫属(Wuchereria spp.)、盘尾丝虫属(Onchocerca spp.)、旋毛线虫属(Spirocerca spp.);
棘头虫纲(Acanthocephala):少棘目(Oligacanthorhynchida),例如:巨吻棘头虫属(Macracanthorhynchus spp.)、前睾棘头虫属(Prosthenorchis spp.);多形目(Polymorphida),例如:细颈棘头虫属(Filicollis spp.);念珠目(Moniliformida),例如:念珠棘虫属(Moniliformis spp.);
棘吻目(Echinorhynchida),例如,棘头虫属(Acanthocephalus spp.)、钩头虫属(Echinorhynchus spp.)、似细吻棘头虫属(Leptorhynchoides spp.);
舌形动物门(Pentastoma):蛇舌状虫目(Porocephalida),例如,舌形虫属(Linguatula spp.)。
在兽医领域和动物饲养中,通过本领域通常已知的方法(如经肠内、胃肠外、真皮或鼻途径)以合适制剂的形式给药式(I)化合物。施用可预防性地或治疗性地进行。
因此,本发明的一个实施方案涉及式(I)化合物作为药物的用途。
另一个方面涉及式(I)化合物作为抗体内寄生虫剂(antiendoparasitic agent),特别是杀蠕虫剂(helminthicidal agent)或抗原生动物剂(antiprotozoic agent)的用途。式(I)化合物适于用作抗体内寄生虫剂、尤其是杀蠕虫剂或抗原生动物剂,例如用于畜牧业、动物饲养、动物笼舍和卫生领域中。
相应地,另一个方面涉及式(I)化合物作为抗体外寄生虫剂(antiectoparasitic)、特别是杀节肢动物剂如杀虫剂或杀螨剂的用途。另一个方面涉及式(I)化合物作为抗体外寄生虫剂、特别是杀节肢动物剂如杀虫剂或杀螨剂的用途,例如用于动物畜牧业、动物饲养、马厩或卫生领域中。
病媒的防治(vector control)
式(I)的化合物还可用于病媒的防治。为本发明的目的,病媒是能将病原体例如病毒、蠕虫、单细胞生物和细菌从贮主(reservoir)(植物、动物、人类等)传播至宿主的节肢动物,尤其是昆虫或蛛形纲动物。所述病原体可被机械地传播至宿主(例如通过无刺苍蝇传播沙眼)或通过注射传播至宿主中(例如通过蚊子传播疟原虫)。
病媒和它们传播的疾病或病原体的实例为:
1)蚊子
-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;
-蚋科属:蠕虫的传播,特别是旋盘尾丝虫(Onchocerca volvulus);
2)虱子:皮肤感染、流行性斑疹伤寒;
3)跳蚤:鼠疫、地方性斑疹伤寒;
4)苍蝇:昏睡病(锥虫病),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、圣路易斯型脑炎、蜱传脑炎(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、包柔氏螺旋体病(borreliosis);
6)蜱:borellioses如杜通氏螺旋体(Borrelia duttoni)、蜱传脑炎、Q热(伯内特考克斯体(Coxiella burnetii))、巴贝西虫病(babesioses)(犬巴贝虫(Babesia caniscanis))。
本发明意义上的病媒的实例为可将植物病毒传播至植物的昆虫,例如蚜虫、苍蝇、叶蝉或蓟马。能传播植物病毒的其他病媒为蛛螨、虱、甲虫和线虫。
本发明意义上的病媒的其他实例为能将病原体传播至动物和/或人的昆虫和蛛形纲动物,如蚊子,尤其是伊蚊属,按蚊属,例如冈比亚按蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、不吉按蚊(A.funestus)、大劣按蚊(A.dirus)(疟疾)和库蚊属,虱,跳蚤,苍蝇,螨虫和蜱。
如果式(I)化合物为抗性突破(resistance-breaking)的,则病媒防治也是可能的。
式(I)化合物适用于预防由病媒传播的疾病和/或病原体。因此,本发明的另一个方面为式(I)化合物,例如在农业、园艺、园林和休闲设施中,以及在材料和储藏产品的保护中,用于病媒防治的用途。
工业材料保护
式(I)化合物适合用于保护工业材料免受昆虫的侵害或破坏,所述昆虫例如来自鞘翅目(Coleoptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鳞翅目(Lepidoptera)、啮虫目(Psocoptera)和衣鱼目(Zygentoma)。
在本文中,工业材料理解为意指无生命材料,如优选塑料、胶粘剂、胶料、纸类和卡片、皮革、木材、木制加工产品和涂料组合物。特别优选本发明用于保护木材的用途。
在另一个实施方案中,式(I)化合物与至少一种其他杀虫剂和/或至少一种杀真菌剂一起使用。
在另一个实施方案中,式(I)化合物以即用型农药的形式存在,即它们可以不经进一步的改变即可应用于所讨论的材料。特别地,合适的其他杀虫剂或杀真菌剂为上述杀虫剂或杀真菌剂。
出人意料地,还已发现,式(I)化合物可用于保护与盐水或半咸水接触的物体免受污染,特别是船体、筛、网、建筑物、系泊设备和信号系统。同样,式(I)化合物可单独地或与其它活性化合物结合地用作为防污剂。
卫生领域中动物有害生物的防治
式(I)化合物适合用于防治卫生领域中的动物有害生物。具体而言,本发明可应用于家用领域、卫生领域和储藏产品的保护中,尤其是用于防治在封闭空间例如住所、工厂大厅、办公室、车厢中遇到的昆虫、蛛形纲动物和螨。为了防治动物有害生物,将式(I)化合物单独使用或与其他活性化合物和/或助剂结合使用。它们优选用于家用杀虫剂产品中。式(I)化合物对敏感物种和抗性物种以及对所有发育阶段都是有效的。
这些害虫包括,例如,以下害虫:蛛形纲(Arachnida),蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足亚纲(Chilopoda)和倍足亚纲(Diplopoda);昆虫纲(Insecta),蜚蠊目(Blattodea)、鞘翅目(Coleoptera)、革翅目(Dermaptera)、双翅目(Diptera)、异翅亚目(Heteroptera)、膜翅目(Hymenoptera)、等翅目(Isoptera)、鳞翅目(Lepidoptera)、虱目(Phthiraptera)、啮虫目(Psocoptera)、跳跃亚目(Saltatoria)或直翅目(Orthoptera)、蚤目(Siphonaptera)和衣鱼目(Zygentoma);以及软甲亚纲(Malacostraca),等足目(Isopoda)。
它们用于例如气雾剂、无压喷雾产品,例如泵喷雾剂及雾化器喷雾剂,自动雾化系统,喷雾剂,泡沫,凝胶,具有由纤维素或塑料制成的蒸发片的蒸发产品,液体蒸发器,凝胶和膜蒸发器,螺旋桨式蒸发器,无能量或无源的蒸发系统,捕蛾纸、捕蛾袋和捕蛾胶,作为颗粒剂或粉末剂,用在散播的饵料中或饵站中。
反应方案
本发明的化合物可通过以下方法制备。
下面示出了本发明化合物(I)的合成路线,其中Z2代表-S(O)1-2-(C1-C2)-烷基、(C1-C2)-卤代烷基或硝基(NO2)。
Z1、Z3、R1、R2、R3和A1代表上述残基。L代表溴或碘,而M代表硼酸、硼酸酯或三氟硼酸酯。Z2代表-S(O)1-2-(C1-C2)-烷基、(C1-C2)-卤代烷基或硝基(NO2)。X代表合适的离去基团如氯或氟。
式(I)化合物(其中Z2代表-S(O)1-2-(C1-C2)-烷基、(C1-C2)-卤代烷基或硝基(NO2))可通过过渡金属(例如钯)催化的式(3)化合物与式(4)化合物的反应合成。这些反应可类似于文献[参见,例如:WO2005-040110;WO2009-089508]中所记载的过程进行。式(4)化合物为市售可得的或可以类似于文献中已知的过程合成。式(3)化合物可由式(1)化合物和相应的吡唑衍生物(2)的亲核取代来制备。类似的反应的实例记载于文献中[参见,例如:EuropeanChemical Bulletin 2013,2(12),981-984;Monatshefte fuer Chemie 1981,112(5),675-678]。本章随后描述式(1)化合物的一般合成路线。
下面示出了本发明(I)的化合物(其中Z2代表-S-(C1-C2)-烷基)的合成路线的实例。
Z1、Z3、R1、R2、R3和A1代表上述残基。Z2代表-S-(C1-C2)-烷基,L代表溴或碘,而M代表代表硼酸、硼酸酯或三氟硼酸酯。X代表合适的离去基团如氯或氟。
式(I)化合物(其中Z2代表-S-(C1-C2)-烷基)可通过过渡金属(例如钯)催化的式(3)化合物与式(4)化合物的反应合成。这些反应可类似于文献[参见,例如:WO2005-040110;WO2009-089508]中所记载的过程进行。式(4)化合物为市售可得的或可以类似于文献中已知的过程合成。式(3)化合物可类似于文献已知的过程由式(5)化合物合成[参见,例如:WO2013-092522]。式(5)化合物可通过式(3a)化合物的还原而制备。合适的还原剂可为氯化锡(II)或铁(0)。实例广泛记载于文献中[参见,例如:Fe(0)WO2012-062783或WO2014-023258;参见,例如:Sn(II)Cl2WO2009-056556或WO2002-016364]。式(3a)化合物可如上文(3)的合成中所述由式(1a)化合物和相应的吡唑衍生物(2)的亲核取代来制备。式(1a)化合物的一般合成路线在以下描述。
下面示出了中心中间体(1a)-(1e)的一般合成。
式(1d)和式(1e)化合物可通过式(1c)化合物的氧化而合成。合适的氧化剂为,例如间氯过苯甲酸和过氧化氢。合适的过程已记载于文献中[参见,例如:氧化至砜:WO2013-018804;WO2007-138050;氧化至亚砜:WO2010-035915;WO2007-138050]。
式(1c)化合物可以类似于文献[参见,例如:WO2013-092522]已知的过程由式(9)化合物合成。式(9)化合物可如上文(5)的合成中所述以类似于文献已知的过程由式(1a)化合物合成。式(1a)化合物可通过硝化反应由式(7)化合物起始来制备。类似的反应记载于文献中[参见,例如:EP1987-110490;DE1985-3528478]。式(7)化合物可通过氯化反应由式(6)化合物起始来制备。类似的反应记载于文献中[参见,例如:WO2012-062783;WO2011-131615]。
式(1b)化合物可由式(8)化合物合成。类似的反应记载于文献中[参见,例如:WO2010-051926,WO2005-095351]。式(8)化合物可通过碘化由式(7)化合物合成。类似的反应记载于于文献中[参见,例如:WO2010-051926,WO2008-098104]。
本发明的一个优选实施方案涉及以下任一中间体
实验部分
2-氯-N-(1-氰基环丙基)-5-[5′-(1-氟环丙基)-2′-甲基-4′-(三氟甲基)-2′H-1,
3′-二吡唑-4-基]苯甲酰胺(I-1)的合成
5-氯-3-(1-氟环丙基)-1-甲基-1H-吡唑(11)
在氩气气氛下,将840mg(5.99mmol)3-(1-氟环丙基)-1-甲基-1H-吡唑溶于10mL无水THF中,并冷却至-75℃。用5.62mL(8.99mmol)正丁基锂于己烷中的1.6M的溶液逐滴处理溶液。将混合物在-75℃下搅拌30分钟。在氩气气氛下将1.70g(7.19mmol)六氯乙烷溶于10mL无水THF中并冷却至-75℃。将吡唑反应混合物经聚四氟乙烯导管缓慢转移至冷却的六氯乙烷溶液中。将合并的反应混合物在-75℃下搅拌1小时。通过加入饱和碳酸钠溶液使反应结束。将反应混合物温热至室温。粗产品用乙酸乙酯萃取几遍。将合并的有机相用MgSO4干燥、过滤并在真空(最高35℃;>80mbar)下浓缩。残余物通过快速色谱法在SiO2上纯化。
分离出535mg 5-氯-3-(1-氟环丙基)-1-甲基-1H-吡唑(11),其为与3-(1-氟环丙基)-1-甲基-1H-吡唑的1∶1混合物,为黄色液体。
GC-MS**):指数=1128,质量(m/z)=174[M]+。
1H-NMR(400MHz,DMSO-d6):6.51(s,1H),3.76(s,3H),1.45-1.30(m,2H),1.10-1.00(m,2H)。
5-氯-3-(1-氟环丙基)-4-碘-1-甲基-1H-吡唑(12)
将上述混合物(535mg)溶于5mL MeCN中。加入266mg I2(1.05mmol)和479mg(NH4)Ce(NO2)6(0.87mmol),并将混合物在回流下搅拌3h,并继续在室温下搅拌过夜。混合物分配于H2O和EtOAc之间。有机层用Na2S2O3水溶液洗涤并用MgSO4干燥。将溶剂蒸发。
分离出863mg 5-氯-3-(1-氟环丙基)-4-碘-1-甲基-1H-吡唑(12),其为与3-(1-氟环丙基)-4-碘-1-甲基-1H-吡唑的混合物,并不经纯化即用于下一步骤。
GC-MS**):指数=1490,质量(m/z)=300[M]+。
1H-NMR(400MHz,DMSO-d6):3.86(s,3H),1.41-1.31(m,2H),1.06-0.99。
5-氯-3-(1-氟环丙基)-1-甲基-4-(三氟甲基)-1H-吡唑(13)
将665mg CuI(3.49mmol)和162mg KF(2.80mmol)溶于6mL无水DMF中,并使溶液用氩气饱和。加入700mg的上面分离出的混合物(12)和994mg三甲基(三氟甲基)硅烷并将混合物在80℃下搅拌6小时。将混合物用EtOAc稀释并用SiO2塞过滤。滤液用H2O洗涤并将有机层用MgSO4干燥。将溶剂蒸发。
分离出776mg粗的5-氯-3-(1-氟环丙基)-1-甲基-4-(三氟甲基)-1H-吡唑(13),其为棕色液体。
GC-MS**):指数=1195,质量(m/z)=242[M]+。
2-氯-N-(1-氰基环丙基)-5-[5′-(1-氟环丙基)-2′-甲基-4′-(三氟甲基)-2′H-1,
3′-二吡唑-4-基]苯甲酰胺(I-1)
在氩气气氛下,将300mg 5-氯-3-(1-氟环丙基)-1-甲基-4-(三氟甲基)-1H-吡唑(13)、121mg 2-氯-N-(1-氰基环丙基)-5-(1H-吡唑-4-基)苯甲酰胺(14)(0.42mmol)和342mg Cs2CO3(1.05mmol)溶于10mL无水DMF中。将混合物在80℃下搅拌过夜。混合物用EtOAc稀释并加入NH4Cl水溶液。用EtOAc萃取该混合物。合并的有机层用H2O和盐水洗涤并用MgSO4干燥。将溶剂蒸发,然后将残余物通过快速色谱法和HPLC纯化。
分离出3mg 2-氯-N-(1-氰基环丙基)-5-[5′-(1-氟环丙基)-2′-甲基-4′-(三氟甲基)-2′H-1,3′-二吡唑-4-基]苯甲酰胺(I-1),其为无色树脂。
HPLC-MS*):请参考表1
1H-NMR数据:请参考峰列表。
所述质量为具有最高强度的[M+H]+离子的同位素模式的峰;如果检测到[M-H]-离子,则将所述质量标记为2。
2所述质量为具有最高强度的[M-H]-离子的同位素模式的峰。如果所述质量通过GCMS(方法参见下文)测量法确定,则将所述质量标记为3。
*)注释:关于logP值的测定和质量检测:所给出的logP值的测定根据EECDirective 79/831 Annex V.A8通过HPLC(高效液相色谱法)在反相色谱柱(C18)上进行。安捷伦1100 LC系统;50*4.6Zorbax Eclipse Plus C18 1.8微米;流动相A:乙腈(0.1%甲酸);流动相B:水(0.09%甲酸);线性梯度为在4.25min内从10%乙腈至95%乙腈,然后95%乙腈持续1.25min;柱温箱温度55℃;流速:2.0ml/min。质量检测通过Agilend MSD系统进行。
**)安捷伦6890 GC,HP5979 MSD,10m DB-1,iD=0.18mm,FILM=0。4μm,Inj.:250℃,恒定流速:1.6mm/min He,Det.:MSD:280℃,FID:320℃,柱温箱:50℃(1min)-40℃/min-320℃(3.25min)
所选实施例的NMR数据
NMR峰列表方法
所选实施例的1H NMR数据以1H NMR峰列表的形式给出。对于每个信号峰,列出以ppm计的δ值并在圆括号中列出信号强度。δ值-信号强度对之间通过分号分开。
因此,一个实例的峰列表具有以下形式:
δ1(强度1);δ2(强度2);........;δi(强度i);......;δn(强度n)
在打印出的以cm计的NMR谱的实例中,尖峰信号的强度与信号的高度相关,并且示出了信号强度的真实比例。对于宽峰信号,可示出若干个峰或信号的中值及其相对于谱图中的最强峰的相对强度。
对于1H NMR谱的化学位移的标定,我们使用四甲基硅烷和/或所用溶剂的化学位移,尤其是在DMSO中测量的谱图的情况下。因此,在NMR峰列表中,四甲基硅烷峰可出现但并不必须出现。
1H NMR峰的列表与常规1H NMR输出图谱相似,因此通常包含在常规NMR解析中列出的所有峰。
此外,与常规1H NMR输出图谱一样,它们可以示出溶剂信号、目标化合物的立体异构体(其同样是本发明的目的)的信号和/或杂质的峰。
为示出溶剂和/或水的δ范围内的化合物的信号,我们的1H NMR峰列表示出了常见的溶剂峰,例如在DMSO-d6中的DMSO的峰,和水的峰,它们通常平均具有高的强度。
目标化合物的立体异构体的峰和/或杂质的峰通常平均具有比目标化合物(例如,纯度>90%)的峰更低的强度。
这类立体异构体和/或杂质可以是特定的制备方法特有的。因此,它们的峰可有助于通过“副产物指纹(side-products-fingerprints)”来确认我们的制备方法的再现性。
通过已知方法(MestreC,ACD模拟,并且使用靠经验估算的期望值)计算目标化合物的峰的专业人员可根据需要任选地使用其他强度过滤器来分离目标化合物的峰。这种分离类似于常规1H NMR解析中的相关峰的拾取。
具有峰列表的NMR数据说明的其他细节见于公开物研究公开数据库(ResearchDisclosure Database)笫564025号的“Citation of NMR Peaklist Data within PatentApplications”。
起始材料的制备
3-(1-氟环丙基)-1-甲基-1H-吡唑(10)的合成
(2E)-3-(二甲基氨基)-1-(1-氟环丙基)丙-2-烯-1-酮(16)
按照J.Med.Chem.2011,54,7974中对于(2E)-3-(二甲基氨基)-1-(环丙基)丙-2-烯-1-酮的描述,由(15)起始合成(2E)-3-(二甲基氨基)-1-(1-氟环丙基)丙-2-烯-1-酮(16)。
HPLC-MS*):logP=1.16,质量(m/z)=158[M+H]+。
1H-NMR(400MHz,DMSO-d6):7.63(d,1H),5.47-5.43(m,1H),3.12(s,3H),2.84(s,3H),1.28-1.10(m,4H)
3-(1-氟环丙基)-1-甲基-1H-吡唑(10)
将685mg(4.35mmol)(2E)-3-(二甲基氨基)-1-(1-氟环丙基)丙-2-烯-1-酮(16)溶于10mL EtOH中并加入0.35mL甲肼(6.53mmol)。将混合物在60℃下搅拌过夜。加入1.16mL甲肼(2.18mmol)并在60℃下再继续搅拌5小时。将混合物冷却至环境温度并将溶剂蒸发。将残余物溶于EtOAc中,然后将溶液用饱和Na2CO3水溶液和盐水洗涤。有机层用MgSO4干燥,然后将溶剂蒸发。残余物通过快速色谱法在SiO2上纯化。
分离出156mg 3-(1-氟环丙基)-1-甲基-1H-吡唑(10),其为与5-(1-氟环丙基)-1-甲基-1H-吡唑的6∶4混合物,且为黄色液体。
GC-MS**):指数=1086,质量(m/z)=140[M]+。
1H-NMR(400MHz,DMSO-d6):7.67(d,1H),6.29(d,1H),3.79(s,3H),1.38-1.30(m,2H),1.07-1.00(m,2H)。
2-氯-N-(1-氰基环丙基)-5-(1H-吡唑-4-基)苯甲酰胺(14)的合成
将2.25g 4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1H-吡唑(17)(11.5mmol)、2.00g 2-氯-N-(1-氰基环丙基)-5-碘代苯甲酰胺(18)(5.77mmol)和667mg Pd(PPh3)4(1.16mmol)溶于186mL 2-丙醇中并加入18mL 1M NaHCO3水溶液。将混合物脱气并回流搅拌过夜。将溶剂蒸发并将残余物溶于EtOAc中。有机层用H2O和盐水洗涤,用MgSO4干燥并将溶剂蒸发。残余物通过快速色谱法在SiO2上纯化。
分离出995mg 2-氯-N-(1-氰基环丙基)-5-(1H-吡唑-4-基)苯甲酰胺(14),其为无色固体。
HPLC-MS*):logP=1.31,质量(m/z)=287[M+H]+。
1H-NMR(400MHz,乙腈-d3):7.93(s,2H),7.66-7.59(m,3H),7.43(d,1H),1.59-1.56(m,2H),1.36-1.32(m,2H)。
下面示出了本发明(I)的化合物(其中Z2代表-CHF2)的合成实例。
Z1、Z3、R1、R2、R3和A1代表上述残基。Z2代表-CHF2,L代表溴或碘,而M代表硼酸、硼酸酯或三氟硼酸酯。X代表合适的离去基团如氯或氟。
式(I)化合物(其中Z2代表-CHF2)可通过过渡金属(例如钯)催化的式(3)化合物与式(4)化合物的反应合成。这些反应可类似于文献[参见,例如:WO2005-040110;WO2009-089508]中所记载的过程进行。式(4)化合物为市售可得的或可以类似于文献中已知的过程合成。式(3)化合物可以类似于文献已知的过程由式(20)化合物合成[参见,例如:US2008-0033013]。式(20)化合物可如上文(3)的合成中所述由式(19)化合物和相应的吡唑衍生物(2)的亲核取代来制备。式(19)化合物的一般合成路线在以下描述。
下面示出了中间体(19)的一般合成。
式(19)化合物可由式(23)化合物合成。类似的反应记载于文献中[参见,例如:Org.Lett.2015,17,932-935.]。式(23)化合物可通过由式(21)化合物与肼衍生物(22)的缩合合成。类似的反应记载于文献中[参见,例如:US2008-0194617]。
2-氯-N-(1-氰基环丙基)-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酰胺(I-2)的合成
5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑-4′-甲醛(25)
将593mg 5-氯-3-(1-氟环丙基)-1-甲基-1H-吡唑-4-甲醛(24)(2.70mmol)加入至840mg 4-碘-1H-吡唑(4.33mmol)和2.20g Cs2CO3(6.76mmo)于无水DMF中的溶液中。将溶液在室温下搅拌16小时。溶液用EtOAc稀释,用NH4Cl溶液洗涤,并且水层用EtOAc萃取。将合并的有机层用盐水洗涤,用MgSO4干燥,然后将溶剂蒸发。残余物通过快速色谱法纯化。
分离出200mg 5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑-4′-甲醛(25),其为无色固体。
HPLC-MS*):logP=2.86,质量(m/z)=376[M+]。
1H-NMR(400MHz,DMSO-d6):9.86(s,1H),8.54(s,1H),8.06(s,1H),3.73(s,3H),1.47-1.46(m,4H)
4′-(二氟甲基)-5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑(26)
将200mg 5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑-4′-甲醛(25)(0.5mmol)溶于10mL CH2Cl2中,然后加入溶于20mL CH2Cl2的542mg N,N-二乙基氨基三氟化硫。将溶液在室温下搅拌48小时。通过加入NaHCO3水溶液使反应结束。用EtOAc萃取混合物。合并的有机相用Na2SO4干燥,然后将溶剂蒸发。
分离出214mg 4′-(二氟甲基)-5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑(26),其为黄色油且不经进一步纯化即用于下一步骤。
HPLC-MS*):logP=3.37,质量(m/z)=398[M+]。
1H-NMR(400MHz,DMSO-d6):8.38(s,1H),8.01(s,1H),6.99(t,1H),3.62(s,3H),1.44-1.43(m,4H)
2-氯-5-[4′(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸甲酯(28)
将189mg 4′-(二氟甲基)-5′-(1-氟环丙基)-4-碘-2′-甲基-2′H-1,3′-二吡唑(26)、170mg 2-氯-5-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)苯甲酸甲酯(27)和22.8mg Pd(PPh3)4溶于5mL 1,4-二氧六环中,然后加入2mL NaHCO3溶液。将混合物在80℃下搅拌16小时。将溶液冷却至室温并经二氧化硅过滤。将滤液浓缩,并将残余物通过快速色谱法纯化。
分离出87mg 2-氯-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸甲酯(28),其为黄色油。
HPLC-MS*):logP=3.63,质量(m/z)=424[M+]。
1H-NMR(400MHz,DMSO-d6):8.77(s,1H),8.50(s,1H),8.12(d,1H),7.93-7.91(m,1H),7.65(d,1H),7.00(t,1H),3.90(s,3H),3.71(s,3H),1.49-1.41(m,2H),1.23-1.16(m,2H)
2-氯-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸(29)
将87mg 2-氯-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸甲酯(28)溶于2mL THF中,然后加入溶于2mL H2O的14.7mg LiOH。将溶液在室温下搅拌3小时。混合物用EtOAc稀释并用HCl 1M和盐水洗涤。有机相用MgSO4干燥,然后将溶剂蒸发。残余物不经进一步纯化即用于下个步骤。
分离出82mg 2-氯-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸(29),其为黄色油。
HPLC-MS*):logP=2.71,质量(m/z)=410[M+]。
2-氯-N-(1-氰基环丙基)-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酰胺(I-2)
将41mg 2-氯-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酸(29)、36.5mg 4-N,N-二甲基氨基吡啶以及57.4mg 1-乙基-3-(3-二甲基氨基丙基)碳二亚胺溶于9mL CH2Cl2和1mL DMF中。将混合物在室温下搅拌12小时。溶液用CH2Cl2稀释并用HCL 1M和盐水洗涤。有机层用MgSO4干燥,然后将溶剂蒸发。残余物通过制备型HPLC纯化。
分离出25mg 2-氯-N-(1-氰基环丙基)-5-[4′-(二氟甲基)-5′-(1-氟环丙基)-2′-甲基-2′H-1,3′-二吡唑-4-基]苯甲酰胺(I-2),其为无色固体。
HPLC-MS*):请参考表1
1H-NMR数据:请参考峰列表。
起始材料的制备
5-氯-3-(1-氟环丙基)-1-甲基-1H-吡唑-4-甲醛(24)的合成
3-(1-氟环丙基)-3-氧代丙酸甲酯(31)
将10g 1-氟环丙烷甲酸(30)溶于80mL CH2Cl2中,并逐滴加入10.9g TMS-CH2N2。将混合物在室温下搅拌1小时。将溶剂蒸发,产品不经进一步纯化即用于下一步骤。
将11.3g乙酸乙酯溶于150mL THF中。在-78℃下逐滴加入122mL LiHMDS 1M的己烷溶液。将混合物在-78℃下搅拌1小时。在-78℃下,逐滴加入8.0g上述溶于150mL THF的甲酯,并将混合物再搅拌3小时。通过加入饱和NH4Cl水溶液使反应结束。使混合物温热至室温,并用EtOAc萃取。合并的有机层用盐水洗涤并用MgSO4干燥。将溶剂蒸发,产品不经进一步纯化即用于下一步骤。
分离出10.9g 3-(1-氟环丙基)-3-氧代丙酸甲酯(31),其为黄色油。
GC-MS**):指数=1502,质量(m/z)=175[M+H]+
5-(1-氟环丙基)-2-甲基-2,4-二氢-3H-吡唑-3-酮(32)
将10.9g 3-(1-氟环丙基)-3-氧代丙酸甲酯(31)溶于150mL甲苯中。在0℃下逐滴加入2.31g溶于100mL甲苯中的甲肼。将混合物加热至100℃并搅拌2小时。将溶剂蒸发,残余物通过快速色谱法纯化。
分离出1.5g 5-(1-氟环丙基)-2-甲基-2,4-二氢-3H-吡唑-3-酮(32),其为黄色固体。
HPLC-MS*):logP=0.38,质量(m/z)=157[M+H]+。
1H-NMR(400MHz,DMSO-d6):11.00(s,1H),5.41(s,1H),3.46(s,3H),1.30-1.18(m,2H),0.99-0.93(m,2H)
5-氯-3-(1-氟环丙基)-1-甲基-1H-吡唑-4-甲醛(24)
将298mg 5-(1-氟环丙基)-2-甲基-2,4-二氢-3H-吡唑-3-酮(32)溶于5mL DMF中,并加入732mg POCl3。将反应物在80℃下搅拌4小时。将溶液冷却至室温并倒至冰上。混合物用CH2Cl2萃取。合并的有机层用MgSO4干燥,并将溶剂蒸发。残余物不经进一步纯化即用于下一步骤。
分离出795mg 5-(1-氟环丙基)-2-甲基-2,4-二氢-3H-吡唑-3-酮(32),其为与DMF的混合的黄色油。
HPLC-MS*):logP=1.71,质量(m/z)=203[M+H]+。
1H-NMR(400MHz,DMSO-d6):3.83(s,3H),1.47-1.43(m,2H)1.19-1.17(m,2H)
生物功效
微小牛蜱(Boophilus microplus)——注射测试(BOOPMI Inj)
溶剂:二甲基亚砜
为制备合适的活性化合物制剂,将10mg活性化合物溶于0.5ml溶剂中,并将该浓缩物用溶剂稀释至所需浓度。
将1μl化合物溶液注射到5只饱食的成年雌性蜱(微小牛蜱)的腹部。将这些蜱转移至复制平皿(replica plate)中并在人工气候室(climate chamber)中培育。
7天后,检测能育卵的产卵情况。将没有明显能育性的卵储存在人工气候室中直到约42天后孵化。100%的功效表示所有卵皆是不育的;0%表示所有的卵皆是能育的。
在该测试中,例如,以下制备实施例的化合物在20μg/动物的施用率下表现出100%的良好活性:I-4
猫栉首蚤(Ctenocephalides felis)——经口测试(CTECFE)
溶剂:二甲基亚砜
为制备合适的活性化合物制剂,将10mg活性化合物溶于0.Sml溶剂中,并将浓缩物用牛血稀释至所需的浓度。
将约20个未喂食的成年猫蚤(猫栉首蚤)置于跳蚤室(flea chambers)中。向底部用石蜡膜封住的血室填充提供有化合物溶液的牛血并置于跳蚤室的纱布(gauze)覆盖的顶部,以使所述蚤能够吮吸血液。将血室加热至37℃,而跳蚤室保持在室温。
2天后,测定以%计的杀死率。100%表示所有蚤均被杀死;0%表示没有蚤被杀死。
在该测试中,例如,以下制备实施例的化合物在100ppm的施用率下表现出100%的良好活性:I-4
铜绿蝇(Lucilia cuprina)——测试(LUCICU)
溶剂:二甲基亚砜
将10mg活性化合物溶于0.5ml二甲基亚砜中。制备一系列稀释液以获得所需比率。
将约20个第一龄期的澳大利亚绵羊绿头苍蝇(铜绿蝇)的幼虫转移至含有切碎的马肉和所需浓度的化合物溶液的试管中。
2天后,测定以%计的杀死率。100%表示所有幼虫均被杀死;0%表示没有幼虫被杀死。
在该测试中,例如,以下制备实施例的化合物在100ppm的施用率下表现出100%的良好活性:I-4
桃蚜(Myzus persicae)——喷洒测试
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,将1重量份的活性化合物与上述量的溶剂混合并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。其他测试浓度通过用含有乳化剂的水稀释而制备。
向被所有龄期的绿桃蚜(Myzus persicae)侵染的大白菜(Brassica pekinensis)的叶片上喷洒所需浓度的活性成分制剂。
6天后,测定以%计的杀死率。100%表示所有蚜虫均已被杀死,而0%表示没有蚜虫被杀死。
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出100%的良好活性:I-9
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出90%的良好活性:I-3、I-7、I-10、I-11、I-12
辣根猿叶虫(Phaedon cochleariae)——喷洒测试
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,将1重量份活性化合物与上述量的溶剂混合,并用含浓度为1000ppm的乳化剂的水稀释至所需浓度。其他测试浓度通过用含乳化剂的水稀释来制备。
使用所需浓度的活性成分制剂喷洒大白菜(Brassica pekinensis)的叶片。干燥后,使芥末甲虫(辣根猿叶虫)的幼虫栖居于叶片。
7天后测定以%计的杀死率。100%表示所有甲虫幼虫均被杀死,而0%表示没有甲虫幼虫被杀死。
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出100%的良好活性:I-2,I-3,I-4,I-6,I-7,I-8,I-9,I-10,I-11,I-12
草地贪夜蛾(Spodoptera frugiperda)——喷洒测试
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,将1重量份活性化合物与上述量的溶剂混合,并用含浓度为1000ppm的乳化剂的水稀释至所需浓度。其他测试浓度通过用含乳化剂的水稀释而制备。
对玉米(Zea mays)的叶片部分(leaf section)喷洒所需浓度的活性成分制剂。干燥后,使夜蛾(Spodoptera frugiperda)的毛虫栖居于叶片部分。
7天后测定以%计的杀死率。100%表示所有毛虫均被杀死,而0%表示没有毛虫被杀死。
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出100%的良好活性:I-2、I-7、I-8
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出83%的良好活性:I-3
二斑叶螨(Tetranychus urticae)——喷洒测试OP-抗性
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与上述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。其他测试浓度通过用含有乳化剂的水稀释而制备。
向被所有龄期的二斑叶螨(Tetranychus urticae)侵染的菜豆(Phaseolusvulgaris)叶片上喷洒所需浓度的活性成分制剂。
6天后,测定以%计的杀死率。100%表示所有叶螨均已被杀死,而0%表示没有叶螨被杀死。
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出100%的良好活性:I-2、I-3、I-4、I-6、I-7、I-8、I-9、I-11、I-12
在该测试中,例如,以下制备实施例的化合物在100g/ha的施用率下表现出90%的良好活性:I-10。
Claims (15)
1.通式(I)的化合物,
其中
Z1代表1-卤化的环丙基;
Z2代表-S(O)0-2-(C1-C2)-烷基、(C1-C2)-卤代烷基,或硝基(NO2);
Z3代表(C1-C2)-烷基;
R1代表氢(H)或(C1-C2)-烷基;
R2代表H或氰基(CN);
R3代表CH3或氯(Cl);
A1代表CH或氮(N)。
2.根据权利要求1所述的化合物,其中A1为CH。
3.根据权利要求1或2所述的化合物,其中A1为CH且R3为Cl。
4.根据前述权利要求中任一项所述的化合物,其中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为-S-CH3、-SO-CH3、-SO2-CH3、CF3、CF2H、Cl、Br、I或NO2;
Z3为CH3。
5.根据前述权利要求中任一项所述的化合物,其中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为-S-CH3、Cl、Br、I、CF3、CF2H或NO2;
Z3为CH3。
6.根据前述权利要求中任一项所述的化合物,其中
Z1为1-氟-环丙基或1-氯-环丙基;
Z2为I、CF3、CF2H或NO2;
Z3为CH3。
7.根据前述权利要求中任一项所述的化合物,其中R1为H。
8.根据权利要求1或4至7中任一项所述的化合物,其中A1为N。
9.根据权利要求8所述的化合物,其中R3为Cl。
10.根据权利要求1至8中任一项所述的通式(I)的化合物用于防治昆虫、蛛形纲动物和线虫的用途。
11.包含至少一种根据权利要求1至9中任一项所述的化合物的药物组合物。
12.根据权利要求1至8中任一项所述的化合物,其用作药物。
13.根据权利要求1至9中任一项所述的化合物用于制备用于防治动物寄生虫的药物组合物的用途。
14.一种化合物,其选自以下:
15.根据权利要求1至9中任一项所述的化合物用于保护植物的繁殖材料的用途。
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PCT/EP2015/068061 WO2016020441A1 (en) | 2014-08-08 | 2015-08-05 | Novel halogen-substituted compounds |
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CN112424170A (zh) * | 2018-07-05 | 2021-02-26 | 拜耳动物保健有限责任公司 | 用于控制节肢动物的新型化合物 |
CN114423740A (zh) * | 2019-07-29 | 2022-04-29 | 拜耳动物保健有限责任公司 | 用于防治节肢动物的吡唑衍生物 |
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BR112017002370B1 (pt) | 2014-08-08 | 2022-11-22 | Janssen Sciences Ireland Uc | Compostos indóis, composição farmacêutica que os compreende e seu uso na inibição da replicação do vírus da gripe |
WO2016174049A1 (en) * | 2015-04-30 | 2016-11-03 | Bayer Animal Health Gmbh | Anti-parasitic combinations including halogen-substituted compounds |
US20180084782A1 (en) * | 2015-05-05 | 2018-03-29 | Syngenta Participations Ag | Method of control of stinkbugs |
BR112018016794B1 (pt) | 2016-02-18 | 2022-07-19 | Syngenta Participations Ag | Compostos derivados de pirazol ativos em termos pesticidas, composição pesticida, método para controle de pragas, método para a proteção de material de propagação vegetal do ataque por pragas e material de propagação vegetal |
WO2018177993A1 (de) | 2017-03-31 | 2018-10-04 | Bayer Cropscience Aktiengesellschaft | Pyrazole zur bekämpfung von arthropoden |
EP3606917A1 (en) | 2017-04-05 | 2020-02-12 | Syngenta Participations AG | Pesticidally active pyrazole derivatives |
BR112022021832A2 (pt) * | 2020-04-29 | 2022-12-13 | Syngenta Crop Protection Ag | Intensificação de culturas |
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- 2015-08-05 WO PCT/EP2015/068061 patent/WO2016020441A1/en active Application Filing
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RU2017107553A (ru) | 2018-09-10 |
EP3177607A1 (en) | 2017-06-14 |
TW201619138A (zh) | 2016-06-01 |
AR101448A1 (es) | 2016-12-21 |
ZA201701640B (en) | 2018-12-19 |
BR112017002508B1 (pt) | 2022-01-18 |
UY36255A (es) | 2016-01-29 |
CA2957308A1 (en) | 2016-02-11 |
AU2015299036B2 (en) | 2020-02-20 |
EP3177607B1 (en) | 2018-09-26 |
BR112017002508A2 (pt) | 2018-06-26 |
CL2017000314A1 (es) | 2017-09-29 |
US20170217899A1 (en) | 2017-08-03 |
JP2017528443A (ja) | 2017-09-28 |
MX2017001789A (es) | 2017-05-23 |
AU2015299036A1 (en) | 2017-02-23 |
WO2016020441A1 (en) | 2016-02-11 |
ES2703853T3 (es) | 2019-03-12 |
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