CN106255686B - 作为害虫防治剂的杂环化合物 - Google Patents
作为害虫防治剂的杂环化合物 Download PDFInfo
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- CN106255686B CN106255686B CN201580022756.9A CN201580022756A CN106255686B CN 106255686 B CN106255686 B CN 106255686B CN 201580022756 A CN201580022756 A CN 201580022756A CN 106255686 B CN106255686 B CN 106255686B
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- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical group CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 229930003945 thebaine Natural products 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- 125000002053 thietanyl group Chemical group 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
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 125000001730 thiiranyl group Chemical group 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- 125000001166 thiolanyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide 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 group COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- 229950004288 tosilate Drugs 0.000 description 1
- IAQRGUVFOMOMEM-ONEGZZNKSA-N trans-but-2-ene Chemical compound C\C=C\C IAQRGUVFOMOMEM-ONEGZZNKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZFDIRQKJPRINOQ-UHFFFAOYSA-N transbutenic acid ethyl ester Natural products CCOC(=O)C=CC ZFDIRQKJPRINOQ-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- FFSJPOPLSWBGQY-UHFFFAOYSA-N triazol-4-one Chemical compound O=C1C=NN=N1 FFSJPOPLSWBGQY-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QFNFRZHOXWNWAQ-UHFFFAOYSA-N triclopyricarb Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NC(Cl)=C(Cl)C=C1Cl QFNFRZHOXWNWAQ-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 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
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 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
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 239000013598 vector Substances 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
- 230000003612 virological effect Effects 0.000 description 1
- 239000012873 virucide Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000010938 white gold Substances 0.000 description 1
- 229910000832 white gold Inorganic materials 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明涉及新的式(I)杂环化合物其中G、R1、R2、Q和V具有说明书中所述的含义,涉及它们的制备方法,以及涉及它们用于防治动物害虫的用途。
Description
本申请涉及新的杂环化合物、用于制备其的方法和中间体、及其用于防治动物害虫的用途。
WO 2012/102387 A1记载了尤其可用作杀虫剂和杀螨剂的杂环化合物。
WO 2004/009597 A2、WO 2008/107418 A1、WO 2009/068617 A1和US 2004/242596A1中公开了用于制药应用的杂环化合物。
Bioorganic&Medicinal Chemistry Letters(2007),17(15),4303-4307报道了特定吡唑并[3,4-d]嘧啶-4-酮的合成和药理学特性。
现代的作物保护组合物必须满足许多要求,例如关于功效、持久性和它们的作用谱以及可能的用途。毒性、环境特性、施用率、与其他活性成分或制剂助剂的可结合性的问题发挥着作用,如同合成活性成分所需的努力的问题一样;此外,可能产生抗性,这里仅提及一些参数。仅基于所有这些原因,不能认为对新的作物保护组合物的探寻已经结束,而是不断需要与已知化合物相比至少在个别方面具有改进的特性的新的化合物。
本发明的一个目的是提供从多个方面拓宽农药谱的化合物。
该目的以及没有明确陈述但可从本文所讨论的关系看出或得出的其他目的通过提供式(I)的化合物而实现
其中
G代表N或C-A1,
A1代表选自以下的基团:氢、卤素、氰基、硝基、烷基、卤代烷基、烷氧基、卤代烷氧基或在每种情况下任选地被取代的环烷基或环烯基,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表NR7R8,或代表在每种情况下任选地被取代的选自以下的基团:烷基、烯基、炔基、烷氧基烷基、烷基-S(O)m-烷基、R7-CO-烷基、NR7R8-CO-烷基、环烷基、环烯基、环烷基烷基、环烯基烷基、杂环基、杂环基烷基、苯基、苯基烷基、杂芳基和杂芳基烷基,
W代表选自以下的基团:O、S、SO和SO2,
X代表选自以下的基团:氢、卤素、氰基、烷基、卤代烷基、烷氧基、卤代烷氧基和环烷基,
Y代表选自以下的基团:氢、卤素、氰基、烷基、卤代烷基、烷氧基、卤代烷氧基、环烷基和NR5R6,
R2代表氢或烷基,
Q代表氮或C-R3,其中
R3代表选自以下的基团:氢、卤素、氰基、硝基、羟基、烷基、卤代烷基、环烷基、烷氧基、卤代烷氧基、环烷基烷基、烷氧基烷基、卤代烷氧基烷基、SH、烷基硫基、烷基亚磺酰基、烷基磺酰基、卤代烷基硫基、卤代烷基亚磺酰基、卤代烷基磺酰基、NH2、烷基氨基和二烷基氨基,
V代表选自以下的基团:氧、硫和NR4,并且
R4代表选自以下的基团:氢、氰基、烷基、卤代烷基、环烷基、硝基、羰基烷基、羰基卤代烷基和羰基烷氧基,
R5代表选自以下的基团:氢、烷基和卤代烷基,
R6代表选自以下的基团:氢、烷基和卤代烷基,
或
R5和R6与它们所键合的氮一起代表任选地被取代的饱和或不饱和的3元至6元环,其任选地包含其他杂原子,
R7代表氢,羟基,或在每种情况下任选地被取代的选自以下的基团:烷基、烷氧基、烷氧基烷基、烷基-S(O)m-烷基、烷基羰基、烷氧基羰基、环烷基、环烯基、环烷基烷基、环烯基烷基、杂环基、杂环基烷基、苯基、苯基烷基、杂芳基和杂芳基烷基,
R8代表氢,金属离子,任选地被取代的铵离子,或在每种情况下任选地被取代的选自以下的基团:烷基、烷氧基、烷氧基烷基、烷基-S(O)m-烷基,并且
m代表选自0、1和2的数。
下面阐述式(I)化合物中所示基团的优选的取代基或范围。其组合形成优选范围(1)。
G代表N或C-A1。
A1代表选自以下的基团:氢、卤素、氰基、C1-C6-烷基、C1-C6-卤代烷基和C3-C6-环烷基。
T代表电子对或氧。
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表NR7R8;或代表C1-C6-烷基、C3-C6-烯基、C3-C6-炔基、C1-C6-烷氧基-C1-C4-烷基、C1-C6-烷基-S(O)m-C1-C4-烷基,其中的每一个任选地被卤素或氰基取代;或代表R7-CO-C1-C4-烷基;或代表NR7R8-CO-C1-C4-烷基;或代表C3-C8-环烷基,其中的每一个任选地被氧(产生C=O)、卤素、氰基、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表C3-C8-环烯基,其中的每一个任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表C3-C6-环烷基-C1-C4-烷基,其任选地被氧(产生C=O)、卤素、氰基、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表C3-C6-环烯基-C1-C4-烷基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表杂环基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表杂环基-C1-C4-烷基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表苯基、苯基-C1-C4-烷基、杂芳基和杂芳基-C1-C4-烷基,其中的每一个任选地被卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基单取代至三取代。
m代表选自0、1和2的数。
W代表选自以下的基团:O、S、SO和SO2。
X代表选自以下的基团:氢、卤素、氰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基和C3-C6-环烷基。
Y代表选自以下的基团:氢、卤素、氰基、C1-C6-烷基、C1-C6-卤代烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基和NR5R6。
R2代表氢或C1-C6-烷基。
Q代表氮或C-R3。
R3代表选自以下的基团:氢、羟基、C1-C6-烷基、C1-C6-卤代烷基、C3-C6-环烷基、C1-C6-烷氧基、C1-C6-卤代烷氧基、C3-C6-环烷基-C1-C4-烷基、C1-C6-烷氧基-C1-C4-烷基、C1-C6-卤代烷氧基-C1-C4-烷基、SH、C1-C6-烷基硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、NH2、C1-C6-烷基氨基和二(C1-C6-烷基)-氨基。
V代表选自以下的基团:氧、硫和NR4。
R4代表选自以下的基团:氢、氰基、C1-C6-烷基、C2-C6-卤代烷基和C3-C6-环烷基。
R5代表选自以下的基团:氢、C1-C6-烷基和C2-C6-卤代烷基。
R6代表选自以下的基团:氢、C1-C6-烷基和C2-C6-卤代烷基。
R5和R6也可与它们所键合的氮原子一起代表饱和至三不饱和的3至6元环,其任选地被卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基取代,特别是氮杂环丙烯基(aziridinyl)、azirenyl、二氮杂环丙烯基、diazirenyl、氮杂环丁烷基(azetidinyl)、dihydroazetyl、二氮杂环丁烷基、dihydrodiazetyl、1,2-氧氮杂环丁烷基(oxazetidinyl)、oxazetyl、硫氮杂环丁烷基(thiazetidinyl)、thiazetyl、吡咯烷基、二氢吡咯基、吡唑烷基、二氢吡唑基、咪唑烷基、二氢咪唑基、噁唑烷基、二氢噁唑基、噻唑烷基、二氢噻唑基(dihydrothyazolyl)、哌啶基、哌嗪基、六氢哒嗪基、六氢嘧啶基、吗啉、二噁嗪基(dioxazinanyl)、硫代吗啉、二噻嗪烷(dithiazinane)、吡咯基、吡唑基、咪唑基、三唑基和四唑基。
R7代表选自以下的基团:氢,羟基,或C1-C6-烷基、C1-C6-烷氧基、C1-C6-烷氧基-C1-C4-烷基、C1-C6-烷基-S(O)m-C1-C4-烷基、C1-C6-烷基羰基、C1-C6-烷氧基羰基、C3-C6-环烷基、C3-C6-环烯基、C3-C6-环烷基-C1-C3-烷基、C3-C6-环烯基-C1-C3-烷基、杂环基、杂环基-C1-C3-烷基,其中的每一个任选地被卤素单取代或多取代或被氰基单取代或二取代;以及代表苯基、苯基-C1-C3-烷基、杂芳基和杂芳基-C1-C3-烷基,其中的每一个任选地被C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C3-C6-环烷基、卤素或氰基单取代至四取代。
R8代表氢、金属离子;或代表任选地被C1-C4-烷基单取代至四取代的铵离子;或代表选自以下的基团:C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基和C1-C4-烷基-S(O)m-烷基,其中的每一个任选地被卤素单取代或多取代或被氰基单取代或二取代。
下面阐述式(I)化合物中所示的基团的特别优选的取代基或范围。其组合形成优选范围(2)。
G代表N或C-A1。
A1代表选自以下的基团:氢、氟、氯、溴、C1-C4-烷基和C1-C4-卤代烷基。
T代表电子对或氧。
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表NR7R8;或代表C1-C6-烷基、C3-C6-烯基、C3-C6-炔基、C1-C4-烷氧基-C1-C3-烷基、C1-C4-烷基-S(O)m-C1-C3-烷基,其中的每一个任选地被卤素单取代至七取代或被氰基单取代或二取代;或代表R7-CO-C1-C2-烷基;或代表NR7R8-CO-C1-C2-烷基;或代表C3-C8-环烷基,其任选地被氧(产生C=O)、卤素、氰基、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表C3-C8-环烯基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表C3-C6-环烷基-C1-C4-烷基,其任选地被氧(产生C=O)、卤素、氰基、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表饱和或不饱和的C3-C6-环烯基-C1-C4-烷基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表杂环基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表杂环基-C1-C4-烷基,其任选地被氧(产生C=O)、C1-C4-烷基、C1-C4-烷氧基和C1-C4-卤代烷基单取代或二取代;或代表苯基、苯基-C1-C3-烷基、杂芳基和杂芳基-C1-C3-烷基,其中的每一个任选地被卤素、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基单取代至三取代。
W代表选自S、SO和SO2的基团。
X代表选自以下的基团:氢、氟、氯、溴、碘、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基。
Y代表选自以下的基团:氢、氟、氯、溴、碘、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基和C1-C4-卤代烷氧基。
R2代表氢或C1-C4-烷基。
Q代表氮或C-R3。
R3代表选自以下的基团:氢、羟基、C1-C4-烷基、C1-C4-卤代烷基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C3-C6-环烷基-C1-C3-烷基、C1-C4-烷氧基-C1-C3-烷基、C1-C4-卤代烷氧基-C1-C3-烷基、SH、C1-C4-烷基硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基、NH2、C1-C4-烷基氨基和二(C1-C4-烷基)-氨基,
V代表氧,
R7代表氢、羟基;或代表选自以下的基团:C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷基-S(O)m-C1-C3-烷基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C3-C6-环烷基、C3-C6-环烷基-C1-C3-烷基、杂环基、杂环基-C1-C3-烷基,其中的每一个任选地被卤素单取代或多取代或被氰基单取代或二取代;以及代表苯基、苄基、吡啶基、嘧啶基、噻唑基、噁唑基、吡唑基、噻吩基、呋喃基、吡啶基甲基和噻唑基甲基,其中的每一个任选地被C1-C4-烷基、C1-C3-卤代烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、环丙基、氟、氯、溴或氰基单取代至三取代,
R8代表氢、金属离子;或代表任选被C1-C4-烷基单取代至四取代的铵离子,或选自以下的基团:C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C2-烷基和C1-C4-烷基-S(O)m-C1-C2-烷基,其中的每一个任选地被卤素单取代或多取代或被氰基单取代或二取代,
m代表选自0、1和2的数。
下面阐述式(I)化合物中所示的基团的非常特别优选的取代基或范围。其组合形成优选范围(3)。
G代表N或C-A1,
A1代表选自以下的基团:氢、氟、氯、溴、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、2,2,2-三氟乙基和2,2-二氟乙基,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表NR7R8;或代表选自以下的基团:C1-C4-烷基、C3-C4-烯基、C3-C4-炔基、C1-C2-烷氧基-C1-C2-烷基和C1-C2-烷基-S(O)m-C1-C2-烷基,其中的每一个任选地被氟、氯单取代、二取代、三取代、四取代或五取代或被氰基二取代;或代表R7-CO-C1-C2-烷基;或代表NR7R8-CO-C1-C2-烷基;或代表C3-C6-环烷基,其任选地被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代或二取代或被氧原子单取代或二取代(产生C=O);或代表C3-C6-环烯基,其任选地被C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代或二取代或被氧原子单取代或二取代(产生C=O);或代表C3-C6-环烷基-C1-C2-烷基,其任选地被卤素、氰基、C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代至二取代;或代表C3-C6-环烯基-C1-C2-烷基,其任选地被C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代或二取代;或代表杂环基,其任选地被C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代或二取代;或代表杂环基-C1-C2-烷基,其任选地被C1-C2-烷基、C1-C2-烷氧基或C1-C2-卤代烷基单取代或二取代;以及代表苯基、苄基、吡啶基、嘧啶基、噻唑基、噁唑基、吡唑基、噻吩基、呋喃基、吡啶基甲基和噻唑基甲基,其中的每一个任选地被氟、氯、溴、氰基、C1-C4-烷基、C1-C4-卤代烷基、C1-C4-烷氧基或C1-C4-卤代烷氧基单取代或二取代。
W代表选自S、SO和SO2的基团,
X代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基和三氟甲氧基,
Y代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基和三氟甲氧基,
R2代表氢或甲基,
Q代表氮或C-R3,
R3代表选自以下的基团:氢、甲基、三氟甲基和环丙基,
V代表氧,
R7代表选自以下的基团:氢,羟基,或C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C4-烷基、C1-C4-烷基-S(O)m-C1-C2-烷基、C1-C4-烷基羰基、C1-C4-烷氧基羰基、C3-C6-环烷基、C3-C6-环烷基-C1-C3-烷基、杂环基和杂环基-C1-C3-烷基,其中的每一个任选地被氟、氯单取代、二取代、三取代、四取代或五取代或被氰基单取代或二取代;以及代表苯基、苄基、吡啶基、嘧啶基、噻唑基、噁唑基、吡唑基、噻吩基、呋喃基、吡啶基甲基和噻唑基甲基,其中的每一个任选地被C1-C4-烷基、C1-C3-卤代烷基、C1-C3-烷氧基、C1-C3-卤代烷氧基、环丙基、氟、氯、溴或氰基单取代至三取代,
R8代表氢、碱金属离子或碱土金属离子、任选地被C1-C4-烷基单取代至四取代的铵离子;或代表选自以下的基团:C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷氧基-C1-C2-烷基和C1-C4-烷基-S(O)m-C1-C2-烷基,其中的每一个任选地氟、氯单取代或多取代或被氰基单取代或二取代,
m代表选自0、1和2的数。
下面阐述式(I)化合物中所示的基团的尤其优选的取代基或范围。其组合形成优选范围(4)。
G代表N或C-A1,
A1代表选自氢和氟的基团,
T代表电子对或氧,
R1代表以下基团中的一个:
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、2-丁烯基、炔丙基、2-丁炔基,其中的每一个任选地被氟单取代、二取代或三取代或被氰基单取代;或代表C3-C6-环烷基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基、乙氧基或三氟甲基单取代;或代表C3-C6-环烷基甲基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基或三氟甲基单取代;或代表苯基、苄基、吡啶基、嘧啶基、噻唑基和吡啶基甲基,其中的每一个任选地被氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基单取代或二取代,
W代表选自S、SO和SO2的基团,
X代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基和三氟甲氧基,
Y代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基和三氟甲氧基,
R2代表氢或甲基,
Q代表氮或C-R3,
R3代表选自以下的基团:氢、甲基、三氟甲基和环丙基,
V代表氧。
下面阐述式(I)化合物中所示的基团的重点优选的取代基或范围。其组合形成优选范围(5)。
G代表N或C-A1,
A1代表选自氢和氟的基团,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、2-丁烯基、炔丙基、2-丁炔基,其中的每一个任选地被氟单取代、二取代或三取代或被氰基单取代;或代表C3-C6-环烷基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基、乙氧基或三氟甲基单取代;或代表C3-C6-环烷基甲基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基或三氟甲基单取代;或代表苯基、苄基、吡啶基、嘧啶基、噻唑基和吡啶基甲基,其中的每一个任选地被氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基单取代或二取代,
W代表选自S、SO和SO2的基团,
X代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
Y代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
R2代表氢或甲基,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
下面阐述式(I)化合物中所示的基团的重点优选的取代基或范围。其组合形成优选范围(6)。
G代表N或C-A1,
A1代表选自氢或氟的基团,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、2-丁烯基、炔丙基、2-丁炔基,其中的每一个任选地被氟单取代、二取代或三取代或被氰基单取代;或代表C3-C6-环烷基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基、乙氧基或三氟甲基单取代;或代表C3-C6-环烷基甲基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基或三氟甲基单取代;或代表苯基、苄基、吡啶基、嘧啶基、噻唑基和吡啶基甲基,其中的每一个任选地被氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基单取代或二取代,
W代表选自S、SO和SO2的基团,
X代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
Y代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
R2代表氢或甲基,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
下面阐述式(I)化合物中所示的基团的还重点优选的取代基或范围。其组合形成优选范围(7)。
G代表N或C-A1,
A1代表选自氢或氟的基团,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、烯丙基、2-丁烯基、炔丙基、2-丁炔基,其中的每一个任选地被氟单取代、二取代或三取代或被氰基单取代;或代表C3-C6-环烷基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基、乙氧基或三氟甲基单取代;或代表C3-C6-环烷基甲基,其任选地被氟、氯、氰基、甲基、乙基、甲氧基或三氟甲基单取代;或代表苯基、苄基、吡啶基、嘧啶基、噻唑基和吡啶基甲基,其中的每一个任选地被氟、氯、溴、氰基、甲基、乙基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、二氟甲氧基或三氟甲氧基单取代或二取代,
W代表选自S、SO和SO2的基团,
X代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
Y代表选自以下的基团:氢、氟、氯、溴、氰基、甲基、乙基和三氟甲基,
R2代表氢或甲基,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
本发明的另一个具体实施方案(优选范围(8))涉及式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表选自甲基、三氟乙基和环丙基甲基的基团,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯和甲基,
Y代表选自氢、氯和甲基的基团,
R2代表氢,
Q代表氮或C-R3,
R3代表氢或甲基,并且
V代表氧。
在优选范围(1)中,除非另有说明,
卤素选自氟、氯、溴和碘,优选依次选自氟、氯和溴,
杂芳基(hetaryl)(与杂芳基(heteroaryl)同义,包括例如杂芳基烷基作为较大单元的一部分)选自呋喃基、噻吩基、吡咯基、吡唑基、咪唑基、1,2,3-三唑基、1,2,4-三唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,3,4-噁二唑基、1,2,5-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,5-噻二唑基、吡啶基、嘧啶基、哒嗪基、吡嗪基、1,2,3-三嗪基、1,2,4-三嗪基、1,3,5-三嗪基、苯并呋喃基、苯并异呋喃基(benzoisofuryl)、苯并噻吩基、苯并异噻吩基(benzoisothienyl)、吲哚基、异吲哚基、吲唑基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、苯并咪唑基、2,1,3-苯并噁二唑、喹啉基、异喹啉基、噌啉基、酞嗪基、喹唑啉基、喹喔啉基、萘啶基、苯并三嗪基、嘌呤基、蝶啶基和中氮茚基,
杂环基代表饱和的3元、4元、5元或6元环,所述环含有1或2个氮原子和/或一个氧原子和/或一个硫原子,但是其中2个氮原子不应直接相邻,例如:氮杂环丙烯基、氮杂环丁烷基、氮杂环戊烷基(azolidinyl)、氮杂环己烷基(azinanyl)、环氧乙烷基(oxiranyl)、氧杂环丁烷基(oxetanyl)、氧杂环戊烷基(oxolanyl)、氧杂环己烷基(oxanyl)、二氧杂环己烷基(dioxanyl)、硫杂环丙烷基基(thiiranyl)、硫杂环丁烷基(thietanyl)、硫杂环戊烷基(thiolanyl)、硫杂环己烷基(thianyl)和四氢呋喃基。
在优选范围(2)中,除非另有说明,
卤素为氟、氯、溴和碘,优选氟、氯和溴,
杂芳基(包括例如杂芳基烷基作为较大单元()的一部分)代表吡啶基、嘧啶基、噻唑基、噁唑基、吡唑基、噻吩基、呋喃基、苄基、吡啶基甲基和噻唑基甲基,并且
杂环基(包括例如杂环基烷基作为较大单元()的一部分)代表饱和或不饱和的3元、4元或5元环,所述环含有1或2个氮原子和/或一个氧原子和/或一个硫原子,但是其中2个氮原子不应直接相邻,例如1-氮杂环丙烯基或2-氮杂环丙烯基,2-环氧乙烷基,2-硫杂环丙烷基,1-氮杂环丁烷基或2-氮杂环丁烷基,2-氧杂环丁烷基或3-氧杂环丁烷基,2-硫杂环丁烷基或3-硫杂环丁烷基,1,3-二氧杂环丁烷-2-基,1-吡咯烷基、2-吡咯烷基或3-吡咯烷基。
在优选范围(3)中,除非另有说明,
卤素代表氟、氯、溴和碘,优选氟、氯和溴,并且
杂环基(包括例如杂环基烷基作为较大单元的一部分)代表饱和或不饱和的3元或4元环,所述环含有1或2个氮原子和/或一个氧原子和/或一个硫原子,但是其中2个氮原子不应直接相邻,例如1-氮杂环丙烯基或2-氮杂环丙烯基、2-环氧乙烷基、2-硫杂环丙烷基、1-氮杂环丁烷基或2-氮杂环丁烷基、2-氧杂环丁烷基或3-氧杂环丁烷基、2-硫杂环丁烷基或3-硫杂环丁烷基、或1,3-二氧杂环丁烷-2-基。
除非另有指明,卤素取代的基团(例如卤代烷基)为单卤代或多卤代的,最高达可能的取代基的最大数目。在多卤代的情况下,卤素原子可相同或不同。在这种情况下,卤素代表氟、氯、溴或碘,尤其是氟、氯或溴。
术语金属离子包括碱金属离子和碱土金属离子,但不限于此。
在本申请中,术语碱金属离子代表选自锂、钠、钾、铷和铯的离子,优选选自锂、钠和钾的离子。
在本申请中,术语碱土金属离子代表选自铍、镁、钙、锶和钡的离子,优选选自镁和钙的离子。
饱和或不饱和的烃基(例如烷基或烯基)可各自是直链或如果可能的话是支链的,包括与杂原子结合,例如在烷氧基中。
除非另有说明,任选地被取代的基团可为单取代或多取代的,其中在多取代的情况下,取代基可相同或不同。
在式(I)化合物中,如果T代表氧,那么这些化合物以N-氧化物的形式存在。
在式(I)化合物中,如果T代表电子对,那么这些化合物以吡啶的形式存在,或对于G=N,以嘧啶的形式存在。
以上给出的一般情况或优选范围内的基团定义或阐述适用于终产物并相应地适用于起始材料和中间体。这些基团定义根据需要彼此结合,即包括在各自的优选范围之间的组合。
根据本发明,优选和优选地使用的是这样的式(I)化合物,其中存在以上列出的作为优选的定义的组合(优选范围(1))。
根据本发明,尤其优选和尤其优选地使用的式(I)化合物,其中存在以上列出的作为特别优选的定义的组合(优选范围(2))。
根据本发明,非常尤其优选和非常尤其优选地使用的式(I)化合物,其中存在以上列出的作为非常尤其优选的定义的组合(优选范围(3))。
本发明的另一个优选的实施方案由优选范围(4)定义。
本发明的另一个优选的实施方案由优选范围(5)定义。
本发明的另一个优选的实施方案由优选范围(6)定义。
本发明的另一个优选的实施方案由优选范围(7)定义。
本发明的另一个优选的实施方案由优选范围(8)定义。
本发明的另一个优选的实施方案涉及式(I)的化合物,其中G代表CH。
本发明的另一个优选的实施方案涉及式(I)的化合物,其中V代表O。
本发明的另一个优选的实施方案涉及式(I)的化合物,其中R1代表下式的基团
本发明的另一个优选的实施方案涉及式(I)的化合物,其中R2代表H。
根据取代基的性质,式(I)化合物也可能为立体异构体的形式,即为几何异构体和/或光学异构体的形式或不同组成的异构体混合物。本发明既提供纯的立体异构体,又提供这些异构体的任何所需混合物,即使在本文中通常只讨论式(I)化合物。
然而,根据本发明优选使用式(I)化合物及其盐的光学活性的、立体异构形式和互变异构形式。
可提及的式(I)化合物的合适的盐为常规无毒盐,即与适当的碱形成的盐和与加成酸形成的盐。优选与无机碱形成的盐,例如碱金属盐(例如钠盐、钾盐或铯盐)、碱土金属盐(例如钙盐或镁盐)、铵盐;与有机碱以及与无机胺形成的盐,例如三乙基铵盐、二环己基铵盐、N,N’-二苄基乙二铵盐、吡啶盐、甲基吡啶盐(picolinium)或乙醇铵盐;与无机酸形成的盐,例如盐酸盐、氢溴酸盐、硫酸二氢盐(dihydrosulphates)、硫酸三氢盐(trihydrosulphates)或磷酸盐;与有机羧酸或有机磺酸形成的盐,例如甲酸盐、乙酸盐、三氟乙酸盐、马来酸盐、酒石酸盐、甲磺酸盐、苯磺酸盐或对甲苯磺酸盐;与碱性氨基酸形成的盐,例如精氨酸盐、天冬氨酸盐或谷氨酸盐等。
互变异构形式在例如R3代表羟基的情况下出现:
因此,本发明涉及用于防治动物害虫(包括节肢动物且特别是昆虫)的纯的对映异构体和非对映异构体及其混合物。
此外,已发现可通过下文所述的方法制备新的式(I)化合物。
例如,可通过方法A-1和A-2以两个步骤制备式(I)化合物,如下文的方案中所示。在该方案和以下的方案中,除非上下文另有说明,Het代表基团
其通过由星号标记的键与吡唑环上的氮连接。
方法A-1和A-2所需要的式(III)氨基吡唑可例如通过方法B和C来制备。
其中Het、Q、R1和R2各自如上定义,R’为氢或烷基(尤其是甲基和乙基),Hal为卤素(优选氯、溴和碘),并且PG为合适的保护基团。
方法A-1
可借助于文献中已知的方法以两个步骤合成式(I)化合物。
在第一合成步骤中,可通过多种方法将式(III)的化合物转化成式(II)的酰胺。当R’=烷基时,该转化过程无需活化即可实现(参见B.M.Trost和I.Fleming在ComprehensiveOrganic Synthesis,Ed.Pergamon,1991,第6卷中)。作为替代方案,文献公开了通过形成氨基化铝(aluminium amide)进行活化的方法(参见T.Ooi和K.Marouka在Science ofSynthesis,Ed.Georg Thieme,2003,第7卷,225-246中)。这些氨基化铝可例如由胺或其盐通过与三甲基铝或它们与1,4-二氮杂二环[2.2.2]辛烷(DABCO)的空气稳定的加合物反应来制备(参见S.Woodward在Tet.Lett.2006,47,5767-5769中)。
作为替代方案,可将其中R’=烷基的式(III)的氨基吡唑经两个阶段转化成式(II)的酰胺:首先水解得到羧酸盐,例如通过与无机碱(优选氢氧化钠和氢氧化钾溶液)反应,所述反应任选使用惰性有机溶剂,可任选地通过用稀酸(例如盐酸水溶液)的酸化来制备和分离其中R’=氢的式(III)的羧酸;随后与所需的胺进行酰胺化反应产生式(II)的化合物。对于酰胺化步骤,已经记载了大量的反应条件,例如G.Benz在ComprehensiveOrganic Synthesis,第1版,Pergamon Press,Oxford,1991,第6卷,第381-417页中;P.D.Bailey等在Comprehensive Organic Functional Group Transformation,第1版,Elsevier Science Ltd.,Oxford,1995,第5卷,第257-308页中和R.C.Larock在Comprehensive Organic Transformations,第2版,Wiley-VCH,纽约,Weinheim,1999,第1929-1994页中。这些反应中的一些通过中间体碳酰氯进行,所述碳酰氯可以单独的形式或在原位产生的形式使用。
酰胺化反应任选地在缩合剂存在下、任选地在酸受体存在下以及任选地在溶剂存在下进行。
可用的缩合剂为通常可用于此类酰胺化反应的所有缩合剂。实例包括酰卤形成剂如光气、三氯化磷、乙二酰氯或亚硫酰氯;碳二亚胺如N,N′-二环己基碳二亚胺(DCC)和1-(3-二甲基氨基丙基)-3-乙基碳二亚胺(EDCI);或其他常规缩合剂如五氧化二磷、多聚磷酸、N,N′-羰基二咪唑、2-氯1-甲碘化吡啶(2-chloropyridine 1-methoiodide)(Mukaiyama's试剂)、2-乙氧基-N-乙氧基羰基-1,2-二氢喹啉(EEDQ)、三苯基膦/四氯化碳、三吡咯烷基溴化鏻六氟磷酸盐(BROP)、O-(1H-苯并三唑-1-基氧基)三(二甲基氨基)鏻六氟磷酸盐(BOP)、N,N,N,N′-二(四亚甲基)氯脲四氟硼酸盐、O-(1H-苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸盐(HBTU)、O-(1H-苯并三唑-1-基)-N,N,N′,N′-二(四亚甲基)脲六氟磷酸盐、O-(1H-苯并三唑-1-基)-N,N,N′,N′-四甲基脲四氟硼酸盐(TBTU)、O-(1H-苯并三唑-1-基)-N,N,N′,N′-二(四亚甲基)脲四氟硼酸盐、O-(7-氮杂苯并三唑-1-基)-N,N,N′,N′-四甲基脲六氟磷酸盐(HATU)、1-羟基苯并三唑(HOBt)和4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉鎓盐(DMT.MM)(通常以氯化物的形式使用)。这些试剂可单独使用或结合使用。
可用的酸受体为所有常规的无机碱或有机碱,例如三乙胺、二异丙基乙胺、N-甲基吗啉或N,N-二甲基氨基吡啶。本发明的方法A任选地在合适的反应助剂例如N,N-二甲基甲酰胺或N,N-二甲基氨基吡啶的存在下进行。可用的溶剂或稀释剂包括所有惰性有机溶剂,例如脂族烃或芳族烃(如石油醚、甲苯)、卤代烃(如氯甲苯、二氯甲烷、氯仿、1,2-二氯乙烷)、醚(如二乙醚、二氧六环、四氢呋喃、1,2-二甲氧基乙烷)、酯(如乙酸乙酯或乙酸甲酯)、硝基烃(如硝基甲烷、硝基乙烷、硝基苯)、腈(如乙腈、苄腈)、酰胺(如N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基甲酰苯胺、N-甲基吡唑烷酮、六甲基磷三酰胺(hexamethylphosphortriamide))以及二甲基亚砜或水或所提及溶剂的混合物。
还可以使用混合酸酐来制备式(III)化合物(参见J.Am.Chem.Soc.1967,5012)。在该方法中,可以使用氯甲酸酯,例如氯甲酸异丁酯和氯甲酸异丙酯。为此目的,也可以使用二乙基乙酰氯、三甲基乙酰氯或类似化合物。
在第二个合成步骤中,可使式(II)的酰胺环化为式(I)的化合物。
在Q=C-R3(其中R3为H或烷基)的情况下,式(II)的酰胺的环化可使用原酸酯(如原甲酸三乙酯或原乙酸三乙酯)进行,任选地在溶剂或稀释剂存在下(例如在醇如乙醇存在下,但也在N,N-二甲基甲酰胺或N,N-二甲基乙酰胺存在下),任选地在催化量或化学计量或过量的有机酸(例如对甲苯磺酸或乙酸)或无机酸(例如盐酸或硫酸)存在下进行。也可使用所提及的酸代替所述溶剂或稀释剂。在R3=H的情况下,与原甲酸三乙酯的反应的这类实例存在于Archiv der Pharmazie 2000,333(8),261-266(用于制备喹唑啉酮)、J.Het.Chem.1990,27(7),1953-1956(同上)和WO 2010/54398(用于制备吡嗪并嘧啶酮(pyrazinopyrimidinones))中。在R3=甲基的情况下,参见例如WO2010/100189(用于制备喹唑啉酮)。
在Q=C-R3(其中R3代表烷基或卤代烷基)的情况下,式(I)的吡唑并嘧啶酮(pyrazolopyrimidinones)也可通过文献中已知的方法使式(II)的酰胺与合适的碳酰卤或羧酸酐反应来制备,所述方法例如,在R3=甲基的情况下记载于WO2009/143049中,在R3=三氟甲基的情况下记载于WO 2008/039489中。
在Q=N的情况下,可根据文献中已知的方法通过式(II)的酰胺的偶氮重氮化(azodiazotization)来制备式(I)的吡唑并嘧啶酮。例如,在0至5℃下,在有机酸或无机酸存在下,通常在水、醇或极性惰性溶剂中用亚硝酸盐(酯)源例如亚硝酸钠或亚硝酸异丁酯处理式(II)化合物。反应条件的实例可见于WO 2004/242572或J.Amer.Chem.Soc.PerkinTrans.1,1980,633-638。
方法A-2
式(I)的N-取代的吡唑并嘧啶酮——其中Q=C-R3,其中R3代表H或烷基——可以两个步骤由式(III)的氨基吡唑通过以下方法来制备:首先转化成式(I-H)的中间体,然后在这些中间体的氮上进行取代。
对于Q=C-H,通过使式(III)的氨基吡唑与乙酸甲脒在甲氧基乙醇中在回流条件下反应过夜而得到式(I-H)的吡唑并嘧啶酮由文献中已知,参见US 2007/0281949。
式(I-H)的吡唑并嘧啶酮的N-取代可以多种方式进行。文献公开了通过在碱和惰性有机溶剂的存在下与合适的芳基底物的SNAr反应进行嘧啶酮的N-芳基化,所述芳基底物为例如通过硝基、腈或三氟甲基基团活化的芳基氟化物,实例参见DE 4431218。对于不同的芳基化合物和杂芳基化合物,反应优选在过渡金属的催化或介入下进行。许多的反应条件的说明记载于文献中,例如WO2007/146824。优选的是,通常在配体——例如二元胺配体,如N,N'-二甲基乙二胺、N,N-二甲基乙二胺或反式-N,N'-二甲基-1,2-环己烷二胺——的存在下,使用铜或铜盐例如碘化铜(I)、氧化铜(I)、三氟甲磺酸铜(I)、或三氟甲磺酸铜(II)作为催化剂。综述见于例如Chem.Sci.2010,第1卷,13-31。作为替代方案,可以使用1,3-二酮,例如2,4-戊二酮、2,2,6,6-四甲基-3,5-庚二酮或二苯甲酰基甲烷;氨基酸,例如L-脯氨酸或甘氨酸;或其他化合物,如8-羟基喹啉(Tetrahedron Lett.2009,第50卷,7293-7296)、二亚苄基丙酮、联吡啶或二氮杂菲。通常,反应在以下条件下进行:在碱的存在下,通常是碳酸盐或磷酸盐的碱,例如碳酸钾、碳酸钠、碳酸铯或磷酸钾;在合适的溶剂中,例如二氧六环、甲苯、二甲基亚砜或N,N-二甲基甲酰胺。还可以使用添加剂,例如碘化钾、氟化铯或其他盐。
或者,可以在钯催化下在配体和碱的存在下在合适的溶剂中进行此类反应,所述钯催化例如使用催化剂,如乙酸钯、四(三苯基膦)钯、双(三苯基膦)氯化钯(II)、三(二亚苄基丙酮)二钯(0),所述配体例如2,2'-双(二苯基膦基)-1,1'-联萘、9,9-二甲基-4,5-双(二苯基膦基)氧杂蒽、1,1'-双(二苯基膦基)二茂铁,所述碱例如碳酸钾、碳酸钠、碳酸铯或磷酸钾,所述溶剂例如二氧六环、甲苯、二甲基亚砜或N,N-二甲基甲酰胺。
作为替代方案,式(I)化合物可通过使适合的硼酸与式(I-H)的吡唑并嘧啶酮反应来制备。通常,所述反应在铜(II)盐例如乙酸铜(II)、三氟甲磺酸铜(II)、或铜(I)盐例如氯化铜(I)、乙酸铜(I)的催化或介入下,在空气或氧气气氛下,通常在脱水条件(例如使用分子筛)下进行。使用的碱为例如在适合的溶剂中的三乙胺、N-乙基二异丙胺、吡啶、2,6-二甲基吡啶、N-甲基吗啉或1,8-二氮杂二环十一碳-7-烯,所述溶剂例如二氯甲烷、二氯乙烷、甲醇、N,N-二甲基甲酰胺、四氢呋喃、二氧六环、乙腈、乙酸乙酯或甲苯。文献中记载了嘧啶酮的大量实例,包括WO 2008/062905或WO 2009/133970。概括性综述见于例如Synthesis2011,第6号,829-856或Tetrahedron 2012,第68卷,7735-7754。除了硼酸,也可以使用其他的硼化合物,例如三氟硼酸钾、硼酸酯等,或其他有机金属化合物,例如锡烷、硅烷或铋烷(bismuthanes)。
方法A-1和A-2中所需的式(III)的氨基吡唑可例如通过方法B和C来制备。
方法B
式(III)和(IIIa)的氨基吡唑可以一个步骤例如通过乌尔曼(Ullmann)反应通过原则上已知的方法(参见Chem.Rev.2008,108,3054-3131)由相应的式(IV)的溴化物和式(V)的氨基吡唑来制备。
氨基吡唑的芳基化的实例记载于WO2007/039146中。对于此类反应,例如,在碱(例如碳酸钾)和配体(例如反式-1,2-二氨基环己烷或反式-N,N′-二甲基-1,2-环己烷二胺)或其组合的存在下,在适合的溶剂(例如二氧六环、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺或吡啶)或溶剂的组合中,使用基于铜(I)的催化剂(例如碘化铜(I))。反应通常需要的温度在80和180℃之间。
在进行本发明的方法B时,可以使用任何适合用于这些反应的市售微波设备(例如Anton Paar Monowave 300,CEM Discover S,Biotage Initiator 60)。
以此方式制备的式(III)和(IIIa)的氨基吡唑可例如通过在硅胶或RP(C-18)上的色谱分离或通过使用适合的溶剂搅拌或重结晶进行分离。
方法C
作为方法B的替代方案,可通过文献中已知的方法由式(VI)的肼或其盐(优选盐酸盐)来制备式(III)的氨基吡唑(参见E.J.Med.Chem.2011,46,3867-3876)。
在步骤1中,式(VI)的肼例如通过与醛(通常为苯甲醛,参见Biorg.Med.Chem.Let2004,14,4585-4589)反应形成式(VII)的腙被保护。被保护的式(VII)化合物通常在惰性有机溶剂(例如醇)中在50℃和100℃之间的温度下与式(IX)的氰基衍生物反应得到式(VIII)的化合物(参见J.Het.Chem.1990,27,1805-1807)(步骤2)。随后在步骤3中式(VIII)化合物与酸(例如盐酸)反应产生式(IIIb)的氨基吡唑。
将硫醚氧化形成亚砜和砜的一般方法
其中W代表SO的式(I)化合物(亚砜)或W代表SO2的式(I)的化合物(砜)可通过文献中已知的方法在合适的溶剂或稀释剂中由其中W代表S的式(I)化合物(硫醚)例如通过氧化剂氧化而制备。合适的氧化剂为例如稀硝酸、过氧化氢、和过氧羧酸,例如间氯过苯甲酸。合适的溶剂或稀释剂为惰性有机溶剂,通常为乙腈和卤代溶剂如二氯甲烷、氯仿或二氯乙烷,以及水和醇,例如甲醇用于使用的反应。
还可以通过方法A-1或A-2引入合适的苯胺R1-NH2、卤化物R1-hal或硼酸R1-B(OH)2,其中W代表SO或SO2。这些可从其中W代表S的相应前体通过文献中已知的方法氧化得到,例如,WO 2013/092350中记载的方法。
许多不同的方法适合于产生富含对映异构体的亚砜,如A.R.Maguire在ARKIVOC,2011(i),1-110中所述:金属催化的硫醚的不对称氧化,例如使用作为最常用的催化剂源的Ti(OiPr4)或VO(acac)2形式的钛和钒以及手性配体和氧化剂,所述氧化剂例如叔丁基氢过氧化物(TBHP)、2-苯基丙-2-基氢过氧化物(CHP)或过氧化氢;使用手性氧化剂或手性催化剂的非金属催化的不对称氧化;亚砜的电化学不对称氧化或生物不对称氧化以及动力学拆分和亲核移位(nucleophilic shift)(根据Andersen方法法)。
所述对映异构体还可由外消旋化合物例如借助手性HPLC通过制备型分离来获得。
起始物料和中间体的说明
式(IV)的卤化物(优选氯化物、溴化物和碘化物)是市售可得的或可通过文献中已知的方法合成,参见例如Y.Yamamoto,Heterocycles 1981,16(7),1161-1164(对于3-碘吡啶(Hal=碘));S.M.E.Englert,J.Amer.Chem.Soc.1929,51(3),863-866(对于3-溴吡啶(Hal=溴));D.E.Pearson,J.Org.Chem.1961,26,789-792(对于3-氯吡啶(Hal=氯));WO2006/074884(对于3-溴-5-氟吡啶)以及M.Schlosser,Eur.J.Org.Chem.2002,24,4174-4180(对于3-氟-5-碘吡啶)。
式(VI)的杂环肼是市售可得的或可通过文献中已知的方法由相应的式(IV)的卤化物制备,如例如WO 2010/015849中所记载,对于不同杂环:通过任选地在惰性有机溶剂(例如乙醇)中,在60和120℃之间的温度下,与水合肼的反应;或通过与肼二羧酸二叔丁酯反应以及随后通过加入酸(通常是在有机溶剂例如二氧六环中的盐酸;也使用三氟乙酸)使羧酸叔丁酯基团裂解,其导致形成了相应的盐。
例如,下列式(VI)的肼是市售可得的:3-肼基吡啶、5-肼基嘧啶。
式(IX)的氰基化合物可根据文献中已知的方法由氰基乙酸烷基酯(优选甲酯和乙酯)制备。
市售可得的实例包括2-氰基-3-乙氧基丙烯酸乙酯(R=R’′=乙基;R2=氢)、2-氰基-3-乙氧基丁-2-烯酸乙酯——也称为2-氰基-3-乙氧基巴豆酸乙酯——(R=R’′=乙基;R2=甲基)、(2E)-2-氰基-3-乙氧基戊-2-烯酸乙酯(R=R’′=R2=乙基)。对于其他烷基基团,式(IX)的氰基化合物的合成可通过J.Amer.Chem.Soc.1956,75,5294-5299中记载的方法进行。这涉及相应的原酸酯(例如在R2=丙基情况下的原丙酸三乙酯)与氰基乙酸烷基酯在相对较高温度下的反应。
式R1-NH2的苯胺是市售可得的或可通过文献中已知的方法制备。它们可分为式(X-1)、式(X-2)和式(X-3)的化合物。
式(X-1)的苯胺由文献例如JP 2007/284356中已知,或它们可通过文献中已知的方法合成。式(X-2)和式(X-3)的苯胺可类似地合成。
其中W代表S的式(X-1)的苯胺可例如如以下方案所示制备。
其中X和Y具有上述含义,AG代表离去基团且PG代表保护基团。
式(XV-1)的苯胺是市售可得的或可通过已知的方法制备。它们可用合适的保护基团例如乙酰基进行保护,作为式(XIV-1)化合物。例如,在酸、酸酐或酰基氯的存在下,可将苯胺(XV-1)转化成相应的酰替苯胺(anilides)(XIV-1)。被保护的苯胺(XIV-1)与氯磺酸的氯磺化得到相应的磺酰氯(XIII-1)。将磺酰氯(XIII-1)还原成二硫化物(XII-1)的反应可通过文献中已知的方法进行,例如盐酸中的铁或碘化物。二硫化物(XII-1)与式(XVI)的卤代烷基亲电体(其中AG为离去基团,例如氯、溴、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)的反应产生硫化物(XI-1)。所述保护基团可通过文献中已知的合适方法去除,从而得到式(X-I)的苯胺。
除了还原成二硫化物(XII-1)之外,还可用合适的还原剂(例如碘/磷)还原磺酰氯(XIII-1),以得到硫代烷基酯(alkyl thioate)(XVIII-1),然后通过适合的方法反应,例如与氢氧化钾溶液的反应,以产生式(XVII-1)的硫醇。硫醇(XVII-1)与式(XVI)的卤代烷基亲电体(其中AG代表离去基团,例如氯、溴、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)的反应得到硫化物(X-1)。
同样优选地,式(X-1)的硫醚可通过以下方案制备:
其中X和Y具有上述含义,AG代表离去基团且PG代表保护基团。
式(XXII-1)的硝基芳族化合物与氯磺酸的氯磺化得到相应的磺酰氯(XXI-1)。将磺酰氯(XXI-1)还原成双(硝基芳基)二硫化物(XX-1)的反应可以通过文献中已知的方法例如与碘化物反应进行。二硫化物(XX-1)还原成二硫烷二基双苯胺(disulphanediyldianilines)(XIX-1)——其中一些作为与相应的氨基芳基硫醇(XVII-1)的混合物形成——的反应可以使用通常已知的还原剂例如氢、任选地借助非均相催化剂例如雷尼镍、活性炭负载的铂或活性炭负载的钯进行。二硫化物(XIX-1)或苯硫酚(XVII-1)与式(XVI)的卤代烷基亲电体(其中AG代表离去基团,例如氯、溴、碘、甲苯磺酸根、甲磺酸根或三氟甲磺酸根)的反应得到式(X-1)的苯胺。
异构体
根据取代基的性质,式(I)的化合物可为几何异构体和/或光学活性异构体的形式或不同组成的相应的异构体混合物。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,本发明既包括纯的立体异构体也包括这些异构体的任何混合物。
方法和用途
本发明还涉及防治动物害虫的方法,其中使式(I)化合物作用于动物害虫和/或它们的生境。动物害虫的防治优选在农业和林业以及材料保护中进行。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和在人体或动物体上进行的诊断方法。
本发明还涉及式(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,在各种情况下,术语“农药”还总是包括术语“作物保护剂”。
鉴于良好的植物耐受性、对温血物种有利的毒性和良好的环境相容性,式(I)化合物适于保护植物和植物器官抵抗生物和非生物胁迫因素;增加采收产量;提高采收物的质量;以及防治在以下领域中遇到的动物害虫:农业、园艺业、畜牧业、水产业、林业、花园以及休闲设施中;贮存产品的保护及材料的保护中;以及卫生领域中尤其是昆虫、蛛形纲动物、蠕虫、线虫和软体动物。它们可优选地用作农药。它们对通常敏感的且具有抗性的物种以及对所有或某些发育阶段有效。上述害虫包括:
节肢动物门(Arthropoda)的害虫,尤其是蛛形纲(Arachnida),例如,粉螨属种(Acarus spp.),例如粗脚粉螨(Acarus siro);枸杞瘤瘿螨(Aceria kuko)、桔芽瘿螨(Aceria sheldoni);刺皮节蜱属种(Aculops spp.);刺锈螨属种(Aculus spp.),例如Aculus fockeui、苹果刺锈螨(Aculus schlechtendali);钝眼蜱属种(Amblyomma spp.);山楂叶螨(Amphitetranychus viennensis);锐缘蜱属种(Argas spp.);牛蜱属种(Boophilus spp.);短须螨属种(Brevipalpus spp.),例如紫红短须螨(Brevipalpusphoenicis);Bryobia graminum、苜蓿苔螨(Bryobia praetiosa);刺尾蝎属种(Centruroides spp.);皮螨属种(Chorioptes spp.);鸡皮刺螨(Dermanyssus gallinae);屋尘螨(Dermatophagoides pteronyssinus)、粉尘螨(Dermatophagoides farinae);革蜱属种(Dermacentor spp.);始叶螨属种(Eotetranychus spp.),例如核桃始叶螨(Eotetranychus hicoriae);梨上瘿螨(Epitrimerus pyri);真叶螨属种(Eutetranychusspp.),例如柑橘褐蜘蛛(Eutetranychus banksi);瘿螨属种(Eriophyes spp.),例如梨上瘿螨(Eriophyes pyri);家食甜螨(Glycyphagus domesticus);红足土螨(Halotydeusdestructor);半跗线螨属种(Hemitarsonemus spp.),例如茶半跗线螨(Hemitarsonemuslatus)(=Polyphagotarsonemus latus);璃眼蜱属种(Hyalomma spp.);硬蜱属种(Ixodesspp.);盗蛛属种(Latrodectus spp.);斜蛛属种(Loxosceles spp.);秋收恙螨(Neutrombicula autumnalis);Nuphersa属种;小爪螨属种(Oligonychus spp.),例如Oligonychus coniferarum、冬青小爪螨(Oligonychus ilicis)、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);纯缘蜱属种(Ornithodorusspp.);禽剌螨属种(Ornithonyssus spp.);全爪螨属种(Panonychus spp.),例如桔全爪螨(Panonychus citri)(=Metatetranychus citri)、苹果全爪螨(Panonychus ulmi)(=Metatetranychus ulmi);柑芸锈螨(Phyllocoptruta oleivora);Platytetranychusmultidigituli;侧多食跗线螨(Polyphagotarsonemus latus);痒螨属种(Psoroptesspp.);扇头蜱属种(Rhipicephalus spp.);根嗜螨属种(Rhizoglyphus spp.);疥螨属种(Sarcoptes spp.);中东金蝎(Scorpio maurus);狭跗线螨属种(Steneotarsonemusspp.),稻细螨(Steneotarsonemus spinki);跗线螨属种(Tarsonemus spp.),例如乱跗线螨(Tarsonemus confusus)、白跗线螨(Tarsonemus pallidus);叶螨属种(Tetranychusspp.),例如四点红蜘蛛(Tetranychus canadensis)、红叶螨(Tetranychuscinnabarinus)、土耳其斯坦叶螨(Tetranychus turkestani)、风团叶螨(Tetranychusurticae);阿氏真恙螨(Trombicula alfreddugesi);Vaejovis属种;番茄刺皮瘿螨(Vasates lycopersici);
唇足亚纲(Chilopoda),例如,地蜈蚣属种(Geophilus spp.)、蚰蜒属种(Scutigera spp.);
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,具斑马陆(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);古巴蠊属种(Panchlora spp.);木蠊属种(Parcoblattaspp.);大蠊属种(Periplaneta spp.),例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplaneta australasiae);棕带蜚蠊(Supella longipalpa);
鞘翅目(Coleoptera),例如,条纹南瓜甲虫(Acalymma vittatum);菜豆象(Acanthoscelides obtectus);喙丽金龟属种(Adoretus spp.);杨树萤叶甲(Agelasticaalni);叩甲属种(Agriotes spp.),例如Agriotes linneatus、小麦金针虫(Agriotesmancus);小粉虫(Alphitobius diaperinus);马铃薯鳃角金龟(Amphimallonsolstitialis);家具窃蠹(Anobium punctatum);星天牛属种(Anoplophora spp.);花象属种(Anthonomus spp.),例如墨西哥棉铃象虫(Anthonomus grandis);圆皮蠹属种(Anthrenus spp.);长喙小象属种(Apion spp.);甘蔗金龟属种(Apogonia spp.);隐食甲属种(Atomaria spp.),例如甜菜隐食甲(Atomaria linearis);毛皮蠹属种(Attagenusspp.);Baris caerulescens;恶条豆象(Bruchidius obtectus);豆象属种(Bruchusspp.),例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus);龟甲属种(Cassidaspp.);菜豆莹叶甲(Cerotoma trifurcata);象甲属种(Ceutorrhynchus spp.),例如白菜籽龟象(Ceutorrhynchus assimilis)、Ceutorrhynchus quadridens、Ceutorrhynchusrapae;凹胫跳甲属种(Chaetocnema spp.),例如甘薯叶甲(Chaetocnema confinis)、Chaetocnema denticulata、Chaetocnema ectypa;方喙象属种(Cleonus mendicus);宽胸叩头虫属种(Conoderus spp.);根颈象属种(Cosmopolites spp.),例如香蕉根茎象(Cosmopolites sordidus);褐新西兰肋翅鳃角金龟(Costelytra zealandica);叩甲属种(Ctenicera spp.);象虫属种(Curculio spp.),例如核桃象甲(Curculio caryae)、Curculio caryatrypes、Curculio obtusus、Curculio sayi;锈赤扁谷盗(Cryptolestesferrugineus)、长角扁谷盗(Cryptolestes pusillus);杨干隐喙象(Cryptorhynchuslapathi)、Cryptorhynchus mangiferae;细枝象属种(Cylindrocopturus spp.),密点细枝象(Cylindrocopturus adspersus)、Cylindrocopturus furnissi;皮蠹属种(Dermestesspp.);叶甲属种(Diabrotica spp.),例如黄瓜条叶甲(Diabrotica balteata)、北方玉米根虫(Diabrotica barberi)、十一星叶甲食根亚虫(Diabrotica undecimpunctatahowardi)、十一星黄瓜甲虫(Diabrotica undecimpunctata undecimpunctata)、西部玉米根虫(Diabrotica virgifera virgifera)、玉米根虫(Diabrotica virgifera zeae);蛀野螟属种(Dichocrocis spp.);水稻铁甲(Dicladispa armigera);Diloboderus属种;食植瓢虫属种(Epilachna spp.),例如南瓜瓢虫(Epilachna borealis)、墨西哥豆象(Epilachnavarivestis);毛跳甲属种(Epitrix spp.),例如黄瓜跳甲(Epitrix cucumeris)、Epitrixfuscula、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrix tuberis);Faustinus属种;裸蛛甲(Gibbium psylloides);阔角谷盗(Gnathocerus cornutus);菜心螟(Hellula undalis);黑异爪蔗金龟(Heteronychusarator);寡节鳃金龟属种(Heteronyx spp.);Hylamorpha elegans;北美家天牛(Hylotrupes bajulus);紫苜蓿叶象(Hypera postica);蓝绿象(Hypomeces squamosus);咪小蠹属种(Hypothenemus spp.),例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemus obscurus)、Hypothenemus pubescens;甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea);烟草甲(Lasioderma serricorne);长头谷盗(Latheticusoryzae);Lathridius属种;合爪负泥虫属种(Lema spp.);马铃薯甲虫(Leptinotarsadecemlineata);银潜蛾属种(Leucoptera spp.),例如咖啡潜叶蛾(Leucopteracoffeella);稻根象(Lissorhoptrus oryzophilus);筒喙象属种(Lixus spp.);黄胸叶甲(Luperomorpha xanthodera);Luperodes属种;粉蠹属种(Lyctus spp.);美洲叶甲属种(Megascelis spp.);梳爪叩头虫属种(Melanotus spp.),例如Melanotus longulusoregonensis;油菜花露尾甲(Meligethes aeneus);鳃金龟属种(Melolontha spp.),例如大栗鳃角金龟(Melolontha melolontha);Migdolus属种;墨天牛属种(Monochamus spp.);象甲(Naupactus xanthographus);隐跗郭公虫属种(Necrobia spp.);黄蛛甲(Niptushololeucus);椰蛀犀金龟(Oryctes rhinoceros);锯谷盗(Oryzaephilus surinamensis);Oryzaphagus oryzae;黑葡萄耳象属种(Otiorhynchus spp.),例如Otiorhynchuscribricollis、Otiorhynchus ligustici、草莓耳喙象(Otiorhynchus ovatus)、草莓根耳喙象(Otiorhynchus rugosostriarus)、黑葡萄耳象(Otiorhynchus sulcatus);小青花金龟(Oxycetonia jucunda);辣根猿叶虫(Phaedon cochleariae);鳃角金龟属种(Phyllophaga spp),Phyllophaga helleri;条跳甲属种(Phyllotreta spp.),例如辣根菜跳甲(Phyllotreta armoraciae)、柔弱黑跳甲(Phyllotreta pusilla)、Phyllotretaramosa、黄曲条菜跳甲(Phyllotreta striolata);日本丽金龟(Popillia japonica);象甲属种(Premnotrypes spp.);大谷蠹(Prostephanus truncatus);蚤跳甲属种(Psylliodesspp.),例如Psylliodes affinis、油菜金头跳甲(Psylliodes chrysocephala)、Psylliodes punctulata;蛛甲属种(Ptinus spp.);暗色瓢虫(Rhizobius ventralis);面炮蠹(Rhizopertha dominica);米象属种(Sitophilus spp.),例如麦子象鼻虫(Sitophilus granarius)、Sitophilus linearis、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais);尖隐喙象属种(Sphenophorus spp.);药材甲(Stegobiumpaniceum);茎干象属种(Sternechus spp.),例如豆茎象(Sternechus paludatus);Symphyletes属种;纤毛象属种(Tanymecus spp.),例如Tanymecus dilaticollis、Tanymecus indicus、Tanymecus palliatus;黄粉虫(Tenebrio molitor);大谷盗(Tenebrioides mauretanicus);拟谷盗属种(Tribolium spp.),例如Tribolium audax、赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Tribolium confusum);斑皮蠹属种(Trogoderma spp.);籽象属种(Tychius spp.);脊虎天牛属种(Xylotrechus spp.);距步甲属种(Zabrus spp.),例如Zabrus tenebrioides;
双翅目(Diptera),例如,伊蚊属种(Aedes spp.),例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、刺扰伊蚊(Aedesvexans);潜蝇属种(Agromyza spp.),例如苜蓿斑潜蝇(Agromyza frontella)、Agromyzaparvicornis;按实蝇属种(Anastrepha spp.);按蚊属种(Anopheles spp.)、例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae);瘿蚊属种(Asphondylia spp.);果实蝇属种(Bactrocera spp.),例如瓜实蝇(Bactroceracucurbitae)、东方果实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae);花园毛蚊(Bibio hortulanus);红头丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina);地中海实蝇(Ceratitis capitata);摇蚊属种(Chironomus spp.);金蝇属种(Chrysomya spp.);斑虻属种(Chrysops spp.);高额麻虻(Chrysozonapluvialis);锥蝇属种(Cochliomya spp.);康瘿蚊属种(Contarinia spp.),例如Contarinia johnsoni、甘蓝瘿蚊(Contarinia nasturtii)、梨叶瘿蚊(Contariniapyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱瘿蚊(Contarinia sorghicola)、麦黄吸浆虫(Contarinia tritici);嗜人瘤蝇(Cordylobia anthropophaga);Cricotopussylvestris;库蚊属种(Culex spp.),例如尖音库蚊(Culex pipiens)、致倦库蚊(Culexquinquefasciatus);库蠓属种(Culicoides spp.);脉毛蚊属种(Culiseta spp.);黄蝇属种(Cuterebra spp.);橄榄实蝇(Dacus oleae);叶瘿蚊属种(Dasineura spp.),例如油菜荚叶瘿蚊(Dasineura brassicae);地种蝇属种(Delia spp.),例如葱地种蝇(Deliaantiqua)、麦地种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Deliaplatura)、甘蓝地种蝇(Delia radicum);人皮蝇(Dermatobia hominis);果蝇属种(Drosophila spp.),例如黄猩猩果蝇(Drosphila melanogaster)、樱桃果蝇(Drosophilasuzukii);稻象属种(Echinocnemus spp.);厕蝇属种(Fannia spp.);胃蝇属种(Gasterophilus spp.);舌蝇属种(Glossina spp.);麻虻属种(Haematopota spp.);毛眼水蝇属种(Hydrellia spp.);大麦水蝇(Hydrellia griseola);种蝇属种(Hylemya spp.);虱蝇属种(Hippobosca spp.);皮下蝇属种(Hypoderma spp.);斑潜蝇属种(Liriomyzaspp.),例如菜斑潜蝇(Liriomyza brassicae)、南美斑潜蝇(Liriomyza huidobrensis)、美洲斑潜蝇(Liriomyza sativae);绿蝇属种(Lucilia spp.),例如铜绿蝇(Luciliacuprina);罗蛉属种(Lutzomyia spp.);曼蚊属种(Mansonia spp.);家蝇属种(Muscaspp.),例如家蝇(Musca domestica)、舍蝇(Musca domestica vicina);狂蝇属种(Oestrusspp.);瑞典麦秆蝇(Oscinella frit);Paratanytarsus属种;Paralauterborniellasubcincta;泉蝇属种(Pegomya spp.),例如甜菜蝇(Pegomya betae)、甜菜潜叶蝇(Pegomyahyoscyami)、悬钩子泉蝇(Pegomya rubivora);白蛉属种(Phlebotomus spp.);草种蝇属种(Phorbia spp.);伏蝇属种(Phormia spp.);酪蝇(Piophila casei);Prodiplosis属种;胡萝卜茎蝇(Psila rosae);绕实蝇属种(Rhagoletis spp.),例如樱桃实蝇(Rhagoletiscingulata)、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);麻蝇属种(Sarcophaga spp.);蚋属种(Simulium spp.),例如南方蚋(Simulium meridionale);螫蝇属种(Stomoxys spp.);虻属种(Tabanus spp.);根斑蝇属种(Tetanops spp.);大蚊属种(Tipula spp.),例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex);
半翅目(Hemiptera),例如,Acizzia acaciaebaileyanae、Acizzia dodonaeae、Acizzia uncatoides;长头蝗(Acrida turrita);无网长管蚜属种(Acyrthosipon spp.),例如碗豆长管蚜(Acyrthosiphon pisum);Acrogonia属种;沫蝉属种(Aeneolamia spp.);隆脉木虱属种(Agonoscena spp.);欧洲甘蓝粉虱(Aleyrodes proletella);甘蔗穴粉虱(Aleurolobus barodensis);软毛粉虱(Aleurothrixus floccosus);Allocaridaramalayensis;芒果叶蝉属种(Amrasca spp.),例如Amrasca bigutulla、叶蝉(Amrascadevastans);飞廉短尾蚜(Anuraphis cardui);肾圆盾介壳虫属种(Aonidiella spp.),例如橘红肾圆盾介壳虫(Aonidiella aurantii)、黄圆蹄盾蚧(Aonidiella citrina)、赤圆介壳虫(Aonidiella inornata);苏联黄粉蚜(Aphanostigma piri);蚜属种(Aphis spp.),例如苹果黄蚜(Aphis citricola)、豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、Aphisforbesi、大豆蚜(Aphis glycines)、棉蚜(Aphis gossypii)、Aphis hederae、Aphisillinoisensis、Aphis middletoni、鼠李马铃薯蚜(Aphis nasturtii)、夹竹桃蚜(Aphisnerii)、苹果蚜(Aphis pomi)、绣线菊蚜(Aphis spiraecola)、Aphis viburniphila;葡萄叶蜂(Arboridia apicalis);Arytainilla属种;小圆盾蚧属种(Aspidiella spp.);薄圆盾介壳虫属种(Aspidiotus spp.),例如常春藤圆盾蚧(Aspidiotus nerii);Atanus属种;茄沟无网蚜(Aulacorthum solani);烟粉虱(Bemisia tabaci);Blastopsyllaoccidentalis;Boreioglycaspis melaleucae;李短尾蚜(Brachycaudus helichrysii);微管蚜属种(Brachycolus spp.);甘蓝蚜(Brevicoryne brassicae);喀木虱属种(Cacopsylla spp.),例如梨木虱(Cacopsylla pyricola);小褐稻虱(Calligyponamarginata);黄头大叶蝉(Carneocephala fulgida);甘蔗绵蚜(Ceratovacuna lanigera);沫蝉科(Cercopidae);蜡蚧属种(Ceroplastes spp.);草莓钉蚜(Chaetosiphonfragaefolii);蔗黄雪盾蚧(Chionaspis tegalensis);茶绿叶蜂(Chlorita onukii);台湾大蝗(Chondracris rosea);核桃黑斑蚜(Chromaphis juglandicola);黑褐圆盾蚧(Chrysomphalus ficus);玉米叶蝉(Cicadulina mbila);Coccomytilus halli;软蚧属种(Coccus spp.),例如褐软蚧(Coccus hesperidum)、长椭圆软蚧(Coccus longulus)、橘软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿软蚧(Coccus viridis);隐瘤蚜(Cryptomyzusribis);Cryptoneossa属种;Ctenarytaina属种;角顶叶蝉属种(Dalbulus spp.);柑橘粉虱(Dialeurodes citri);柑橘木虱(Diaphorina citri);白背盾蚧属种(Diaspis spp.);草履介壳虫属种(Drosicha spp.);西圆尾蚜属种(Dysaphis spp.),例如Dysaphisapiifolia、车前圆尾蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphis tulipae);灰粉蚧属种(Dysmicoccus spp.);小绿叶蝉属种(Empoasca spp.),例如Empoasca abrupta、马铃薯小绿叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、Empoascasolana、Empoasca stevensi;绵蚜属种(Eriosoma spp.),例如Eriosoma americanum、苹果绵蚜(Eriosoma lanigerum)、Eriosoma pyricola;斑叶蝉属种(Erythroneura spp.);Eucalyptolyma属种;褐木虱属种(Euphyllura spp.);Euscelis bilobatus;弗氏粉蚧属种(Ferrisia spp.);咖啡地粉蚧(Geococcus coffeae);Glycaspis属种;银合欢木虱(Heteropsylla cubana)、Heteropsylla spinulosa;假桃病毒叶蝉(Homalodiscacoagulata);桃大尾蚜(Hyalopterus arundinis),桃粉蚜(Hyalopterus pruni);吹绵蚧属种(Icerya spp.),例如吹绵蚧(Icerya purchasi);片角叶蝉属种(Idiocerus spp.);扁喙叶蝉属种(Idioscopus spp.);灰飞虱(Laodelphax striatellus);蜡蚧属种(Lecaniumspp.),例如褐盔蜡蚧(Lecanium corni)(=Parthenolecanium corni);牡蛎蚧属种(Lepidosaphes spp.),例如榆蛎盾蚧(Lepidosaphes ulmi);萝卜蚜(Lipaphis erysimi);斑衣蜡蝉(Lycorma delicatula);长管蚜属种(Macrosiphum spp.),例如马铃薯长管蚜(Macrosiphum euphorbiae)、Macrosiphum lilii、蔷薇长管蚜(Macrosiphum rosae);二点叶蜂(Macrosteles facifrons);突眼长蝽属种(Mahanarva spp.);高粱蚜(Melanaphissacchari);Metcalfiella属种;Metcalfa pruinosa;麦无网蚜(Metopolophiumdirhodum);黑缘平翅斑蚜(Monellia costalis);Monelliopsis pecanis;瘤蚜属种(Myzusspp.),例如冬葱蚜(Myzus ascalonicus)、Myzus cerasi、Myzus ligustri、Myzusornatus、桃蚜(Myzus persicae)、烟蚜(Myzus nicotianae);莴苣衲长管蚜(Nasonoviaribisnigri);黑尾叶蝉属种(Nephotettix spp.),例如黑尾叶蝉(Nephotettixcincticeps)、二条斑黑尾叶蝉(Nephotettix nigropictus);稻褐飞虱(Nilaparvatalugens);Oncometopia属种;Orthezia praelonga;中华稻蝗(Oxya chinensis);Pachypsylla属种;杨梅缘粉虱(Parabemisia myricae);木虱属种(Paratrioza spp.),例如Paratrioza cockerelli;片盾蚧属种(Parlatoria spp.);瘿绵蚜属种(Pemphigusspp.),例如囊柄瘿绵蚜(Pemphigus bursarius)、Pemphigus populivenae;玉米蜡蝉(Peregrinus maidis);绵粉蚧属种(Phenacoccus spp.),例如苏铁褐点并盾蚧(Phenacoccus madeirensis);杨平翅绵蚜(Phloeomyzus passerinii);忽布疣蚜(Phorodon humuli);葡萄根瘤蚜属种(Phylloxera spp.),例如Phylloxera devastatrix、Phylloxera notabilis;苏铁褐点并盾蚧(Pinnaspis aspidistrae);臀纹粉蚧属种(Planococcus spp.),例如枯臀纹粉蚧(Planococcus citri);Prosopidopsylla flava;梨形原绵蚧(Protopulvinaria pyriformis);桑白盾蚧(Pseudaulacaspis pentagona);粉蚧属种(Pseudococcus spp.),例如嗜桔粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、长尾粉蚧(Pseudococcus longispinus)、真葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni);Psyllopsis属种;木虱属种(Psylla spp.),例如Psylla buxi、苹果木虱(Psylla mali)、梨木虱(Psylla pyri);金小蜂属种(Pteromalus spp.);Pyrilla属种;笠圆盾蚧属种(Quadraspidiotus spp.),例如胡桃圆盾蚧(Quadraspidiotus juglansregiae)、Quadraspidiotus ostreaeformis、梨圆盾蚧(Quadraspidiotus perniciosus);Quesada gigas;平刺粉蚧属种(Rastrococcusspp.);缢管蚜属种(Rhopalosiphum spp.),例如玉米蚜(Rhopalosiphum maidis)、Rhopalosiphum oxyacanthae、禾谷缢管蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphum rufiabdominale);黑盔蚧属种(Saissetia spp.),例如咖啡硬介壳虫(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、橄榄黑盔蚧(Saissetiaoleae);葡萄带叶蝉(Scaphoideus titanus);麦二叉蚜(Schizaphis graminum);苏铁刺圆盾蚧(Selenaspidus articulatus);麦长管蚜(Sitobion avenae);长唇基飞虱属种(Sogata spp.);白背飞虱(Sogatella furcifera);Sogatodes属种;三角蝶(Stictocephala festina);树粉虱(Siphoninus phillyreae);Tenalaphara malayensis;Tetragonocephela属种;美洲山核桃长斑蚜(Tinocallis caryaefoliae);广胸沫蝉属种(Tomaspis spp.);声蚜属种(Toxoptera spp.),例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxoptera citricidus);温室白粉虱(Trialeurodes vaporariorum);尖翅木虱属种(Trioza spp.),例如Trioza diospyri;小叶蝉属种(Typhlocyba spp.);尖盾蚧属种(Unaspis spp.);葡萄根瘤虱(Viteus vitifolii);么叶蝉属种(Zygina spp.);
异翅亚目(Heteroptera),例如,南瓜缘蝽(Anasa tristis);拟丽蝽属种(Antestiopsis spp.);Boisea属种;土长蝽属种(Blissus spp.);俊盲蝽属种(Calocorisspp.);斑腿微刺盲蝽(Campylomma livida);异背长蝽属种(Cavelerius spp.);臭虫属种(Cimex spp.),例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、蝠臭虫(Cimex pilosellus);白瓣麦寄蝇属种(Collaria spp.);绿盲蝽(Creontiades dilutus);胡椒缘蝽(Dasynus piperis);Dichelops furcatus;厚氏长棒网蝽(Diconocoris hewetti);棉红蝽属种(Dysdercus spp.);美洲蝽属种(Euschistusspp.),例如Euschistus heros、褐臭蝽(Euschistus servus)、Euschistus tristigmus、Euschistus variolarius;扁盾蝽属种(Eurygaster spp.);茶翅蝽(Halyomorpha halys);刺盲蝽属种(Heliopeltis spp.);Horcias nobilellus;稻缘蝽属种(Leptocorisa spp.);异稻缘蝽(Leptocorisa varicornis);Leptoglossus occidentalis;叶足缘蝽(Leptoglossus phyllopus);丽盲蝽属种(Lygocoris spp.),例如原丽盲蝽(Lygocorispabulinus);草盲蝽属种(Lygus spp.),例如Lygus elisus、豆荚盲蝽(Lygus hesperus)、牧草盲蝽(Lygus lineolaris);蔗黑长蝽(Macropes excavatus);黑摩盲蝽(Monalonionatratum);绿蝽属种(Nezara spp.),例如稻绿蝽(Nezara viridula);稻蝽属种(Oebalusspp.);方背皮蝽(Piesma quadrata);壁蝽属种(Piezodorus spp.),例如Piezodorusguildinii;杂盲蝽属种(Psallus spp.);Pseudacysta persea;长红猎蝽属种(Rhodniusspp.);可可褐盲蝽(Sahlbergella singularis);Scaptocoris castanea;黑蝽属种(Scotinophora spp.);梨冠网蝽(Stephanitis nashi);Tibraca属种;锥猎蝽属种(Triatoma spp.);
膜翅目(Hymenoptera),例如,顶切叶蚁属种(Acromyrmex spp.);残青叶蜂属种(Athalia spp.),例如芜菁叶蜂(Athalia rosae);切叶蚁属种(Atta spp.);松叶蜂属种(Diprion spp.),例如类欧松叶蜂(Diprion similis);实叶蜂属种(Hoplocampa spp.),例如樱实叶蜂(Hoplocampa cookei)、苹叶蜂(Hoplocampa testudinea);毛蚁属种(Lasiusspp.);阿根廷蚁(Linepithema humile);小家蚁(Monomorium pharaonis);Sirex属种;红火蚁(Solenopsis invicta);蚁属种(Tapinoma spp.);树蜂属种(Urocerus spp.);胡蜂属种(Vespa spp.),例如黄边胡蜂(Vespa crabro);黑树蜂属种(Xeris spp.);
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,家白蚁属种(Coptotermes spp.),例如台湾乳白蚁(Coptotermes formosanus);堆角白蚁(Cornitermes cumulans);堆砂白蚁属种(Cryptotermes spp.);楹白蚁属种(Incisitermes spp.);稻麦小白蚁(Microtermesobesi);土白蚁属种(Odontotermes spp.);散白蚁属种(Reticulitermes spp.),例如黄肢散白蚁(Reticulitermes flavipes)、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);褐带卷蛾属种(Adoxophyes spp.),例如棉褐带卷蛾(Adoxophyesorana);烦夜蛾(Aedia leucomelas);地老虎属种(Agrotis spp.),例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon);波纹夜蛾属种(Alabama spp.),例如棉叶波纹夜蛾(Alabama argillacea);脐橙螟蛾(Amyelois transitella);条麦蛾属种(Anarsiaspp.);干煞夜蛾属种(Anticarsia spp.),例如大豆夜蛾(Anticarsia gemmatalis);条小卷蛾属种(Argyroploce spp.);甘蓝夜蛾(Barathra brassicae);籼弄蝶(Borbocinnara);棉潜蛾(Bucculatrix thurberiella);松尺蠖(Bupalus piniarius);蛀褐夜蛾属种(Busseola spp.);卷叶蛾属种(Cacoecia spp.);茶细蛾(Caloptilia theivora);烟卷蛾(Capua reticulana);苹果蠹蛾(Carpocapsa pomonella);桃柱果蛾(Carposinaniponensis);冬尺蛾(Cheimatobia brumata);禾草螟属种(Chilo spp.),例如禾草螟(Chilo plejadellus)、二化螟(Chilo suppressalis);色卷蛾属种(Choristoneuraspp.);葡萄果蠹蛾(Clysia ambiguella);纵卷叶野螟属种(Cnaphalocerus spp.);稻纵卷叶螟(Cnaphalocrocis medinalis);云卷蛾属种(Cnephasia spp.);细蛾属种(Conopomorpha spp.);球颈象属种(Conotrachelus spp.);Copitarsia属种;小卷蛾属种(Cydia spp.),例如豌豆小卷蛾(Cydia nigricana)、苹果小卷蛾(Cydia pomonella);Dalaca noctuides;绢野螟属种(Diaphania spp.);小蔗螟(Diatraea saccharalis);钻夜蛾属种(Earias spp.);Ecdytolopha aurantium;南美玉米苗斑螟(Elasmopalpuslignosellus);非洲蔗螟(Eldana saccharina);粉斑螟属种(Ephestia spp.),例如烟草粉螟(Ephestia elutella)、地中海粉螟(Ephestia kuehniella);叶小卷蛾属种(Epinotiaspp.);苹淡褐卷蛾(Epiphyas postvittana);荚斑螟属种(Etiella spp.);棕卷蛾属种(Eulia spp.);女贞细卷蛾(Eupoecilia ambiguella);黄毒蛾属种(Euproctis spp.),例如褐尾蠹(Euproctis chrysorrhoea);切夜蛾属种(Euxoa spp.);脏切夜蛾属种(Feltiaspp.);大蜡螟(Galleria mellonella);细蛾属种(Gracillaria spp.);小食心虫属种(Grapholitha spp.),例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholitaprunivora);蚀叶野螟属种(Hedylepta spp.);铃夜蛾属种(Helicoverpa spp.),例如棉铃虫(Helicoverpa armigera)、玉米穗虫(Helicoverpa zea);实夜蛾属种(Heliothisspp.),例如烟芽夜蛾(Heliothis virescens);褐织蛾(Hofmannophilapseudospretella);同斑螟属种(Homoeosoma spp.);长卷蛾属种(Homona spp.);苹果巢蛾(Hyponomeuta padella);柿蒂虫(Kakivoria flavofasciata);贪夜蛾属种(Laphygmaspp.);茄黄斑螟蛾(Leucinodes orbonalis);潜叶蛾属种(Leucoptera spp.),例如咖啡潜叶蛾(Leucoptera coffeella);潜叶细蛾属种(Lithocolletis spp.),例如Lithocolletisblancardella;绿果冬夜蛾(Lithophane antennata);花翅小卷蛾属种(Lobesia spp.),例如葡萄花翅小卷蛾(Lobesia botrana);白缘豆夜蛾(Loxagrotis albicosta);毒蛾属种(Lymantria spp.),例如舞毒蛾(Lymantria dispar);潜蛾属种(Lyonetia spp.),例如桃潜蛾(Lyonetia clerkella);黄褐天幕毛虫(Malacosoma neustria);豆荚野螟(Marucatestulalis);甘蓝夜蛾(Mamestra brassicae);暮眼蝶(Melanitis leda);毛胫夜蛾属种(Mocis spp.);Monopis obviella;东方粘虫(Mythimna separata);Nemapogoncloacellus;水螟属种(Nymphula spp.);Oiketicus属种;麦秆夜蛾属种(Oria spp.);瘤丛螟属种(Orthaga spp.);秆野螟属种(Ostrinia spp.),例如欧洲玉米螟(Ostrinianubilalis);黑角负泥虫(Oulema melanopus)、稻负泥虫(Oulema oryzae);小眼夜蛾(Panolis flammea);稻弄蝶属种(Parnara spp.);红铃麦蛾属种(Pectinophora spp.),例如棉红铃虫(Pectinophora gossypiella);潜跳甲属种(Perileucoptera spp.);块茎蛾属种(Phthorimaea spp.),例如马铃薯块茎蛾(Phthorimaea operculella);桔潜蛾(Phyllocnistis citrella);小潜细蛾属种(Phyllonorycter spp.),例如斑幕潜叶蛾(Phyllonorycter blancardella)、Phyllonorycter crataegella;菜粉蝶属种(Pierisspp.),例如菜青虫(Pieris rapae);荷兰石竹小卷蛾(Platynota stultana);印度谷蛾(Plodia interpunctella);金翅夜蛾属种(Plusia spp.);小菜蛾(Plutella xylostella)(=Plutella maculipennis);小白巢蛾属种(Prays spp.);斜纹夜蛾属种(Prodeniaspp.);烟草天蛾属种(Protoparce spp.);粘虫属种(Pseudaletia spp.),例如一星粘虫(Pseudaletia unipuncta);大豆尺夜蛾(Pseudoplusia includens);玉米螟(Pyraustanubilalis);薄荷灰夜蛾(Rachiplusia nu);禾螟属种(Schoenobius spp.),例如Schoenobius bipunctifer;白禾螟属种(Scirpophaga spp.),例如稻白螟(Scirpophagainnotata);黄地老虎(Scotia segetum);蛀茎夜蛾属种(Sesamia spp.),例如大螟(Sesamia inferens);长须卷蛾属种(Sparganothis spp.);灰翅夜蛾属种(Spodopteraspp.),例如Spodoptera eradiana、甜菜夜蛾(Spodoptera exigua)、草地贪夜蛾(Spodoptera frugiperda)、Spodoptera praefica;举肢蛾属种(Stathmopoda spp.);花生麦蛾(Stomopteryx subsecivella);兴透翅蛾属种(Synanthedon spp.);安第斯马铃薯块茎蛾(Tecia solanivora);大显夜蛾(Thermesia gemmatalis);木塞谷蛾(Tineacloacella)、袋谷蛾(Tinea pellionella);幕谷蛾(Tineola bisselliella);栎绿卷蛾属种(Tortrix spp.);毛毡衣蛾(Trichophaga tapetzella);粉夜蛾属种(Trichoplusiaspp.),例如粉纹夜蛾(Trichoplusia ni);三化螟(Tryporyza incertulas);番茄斑潜蝇(Tuta absoluta);灰蝶属种(Virachola spp.);
直翅目(Orthoptera)或跳跃亚目(Saltatoria),例如,家蟋(Achetadomesticus);Dichroplus属种;蝼蛄属种(Gryllotalpa spp.),例如欧洲蝼蛄(Gryllotalpa gryllotalpa);蔗蝗属种(Hieroglyphus spp.);飞蝗属种(Locusta spp.),例如东亚飞蝗(Locusta migratoria);黑蝗属种(Melanoplus spp.),例如Melanoplusdevastator;Paratlanticus ussuriensis;沙漠蝗(Schistocerca gregaria);
虱目(Phthiraptera),例如,牛羽虱属种(Damalinia spp.)、血虱属种(Haematopinus spp.)、毛虱属种(Linognathus spp.)、虱属种(Pediculus spp.)、Phylloera vastatrix、阴虱(Phthirus pubis)、嚼虱属种(Trichodectes spp.);
啮虫目(Psocoptera),例如,粉啮虫属种(Lepinotus spp.)、书虱属种(Liposcelis spp.);
蚤目(Siphonaptera),例如,角叶蚤属种(Ceratophyllus spp.);栉首蚤属种(Ctenocephalides spp.),例如犬栉首蚤(Ctenocephalides canis)、猫栉头蚤(Ctenocephalides felis);扰蚤(Pulex irritans);穿皮潜蚤(Tunga penetrans);印鼠客蚤(Xenopsylla cheopsis);
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;花蓟马属种(Frankliniella spp.),例如烟褐花蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、东方花蓟马(Frankliniella tritici)、Frankliniella vaccinii、威廉期花蓟马(Frankliniellawilliamsi);阳蓟马属种(Heliothrips spp.);温室条篱蓟马(Hercinothripsfemoralis);葡萄蓟马(Rhipiphorothrips cruentatus);硬蓟马属种(Scirtothripsspp.);Taeniothrips cardamomi;蓟马属种(Thrips spp.),例如南黄蓟马(Thripspalmi)、葱蓟马(Thrips tabaci);
衣鱼目(Zygentoma)(=缨尾目(Thysanura)),例如,栉衣鱼属种(Ctenolepismaspp.)、衣鱼(Lepisma saccharina)、盗火虫(Lepismodes inquilinus)、小灶衣鱼(Thermobia domestica);
综合纲(Symphyla),例如,么蚰属种(Scutigerella spp.),例如白松虫(Scutigerella immaculata);
软体动物门(Mollusca),特别是来自双壳纲(Bivalvia)的害虫,例如,贻贝属种(Dreissena spp.),
以及腹足纲(Gastropoda),例如,阿勇蛞蝓属种(Arion spp.),例如黑蛞蝓(Arionater rufus);双脐螺属种(Biomphalaria spp.);泡螺属种(Bulinus spp.);野蛞蝓属种(Deroceras spp.),例如光滑野蛞蝓(Deroceras laeve);土蜗属种(Galba spp.);椎实螺属种(Lymnaea spp.);钉螺属种(Oncomelania spp.);福寿螺属种(Pomacea spp.);琥珀螺属种(Succinea spp.);
来自扁形动物门(Platyhelminthes)和线虫动物门(Nematoda)的动物寄生虫和人类寄生虫,例如,猫圆线虫属种(Aelurostrongylus spp.)、裂口线虫属种(Amidostomumspp.)、钩口线虫属种(Ancylostoma spp.)、管圆线虫属种(Angiostrongylus spp.)、异尖线虫属种(Anisakis spp.)、裸头绦虫属种(Anoplocephala spp.)、蛔虫属种(Ascarisspp.)、鸡蛔虫属种(Ascaridia spp.)、贝利蛔虫属种(Baylisascaris spp.)、布鲁线虫属种(Brugia spp.)、仰口线虫属种(Bunostomum spp.)、毛细线虫属种(Capillaria spp.)、夏柏特线虫属种(Chabertia spp.)、支睾吸虫属种(Clonorchis spp.)、古柏线虫属种(Cooperia spp.)、环体线虫属种(Crenosoma spp.)、杯口属种(Cyathostoma spp.)、双腔吸虫属种(Dicrocoelium spp.)、网尾线虫属种(Dictyocaulus spp.)、裂头绦虫属种(Diphyllobothrium spp.)、复孔绦虫属种(Dipylidium spp.)、恶丝虫属种(Dirofilariaspp.)、龙线虫属种(Dracunculus spp.)、棘球绦虫属种(Echinococcus spp.)、棘口吸虫属种(Echinostoma spp.)、蛲虫属种(Enterobius spp.)、真鞘属种(Eucoleus spp.)、片形吸虫属种(Fasciola spp.)、拟片形吸虫属种(Fascioloides spp.)、姜片虫属种(Fasciolopsis spp.)、类丝虫属种(Filaroides spp.)、筒线属种(Gongylonema spp.)、三代虫属种(Gyrodactylus spp.)、丽线虫属种(Habronema spp.)、血矛线虫属种(Haemonchus spp.)、螺旋线虫属种(Heligmosomoides spp.)、异刺线虫属种(Heterakisspp.)、膜壳绦虫属种(Hymenolepis spp.)、猪圆形属种(Hyostrongylus spp.)、光丝虫属种(Litomosoides spp.)、罗阿丝虫属种(Loa spp.)、后圆线虫属种(Metastrongylusspp.)、次睾吸虫属种(Metorchis spp.)、中殖孔绦虫属种(Mesocestoides spp.)、蒙尼茨绦虫属种(Moniezia spp.)、缪勒线虫属种(Muellerius spp.)、板口线虫属种(Necatorspp.)、细颈线虫属种(Nematodirus spp.)、日本圆线虫属种(Nippostrongylus spp.)、结节线虫属种(Oesophagostomum spp.)、沃鲁线虫属种(Ollulanus spp.)、盘尾丝虫属种(Onchocerca spp.)、后睾吸虫属种(Opisthorchis spp.)、奥斯勒线虫属种(Oslerusspp.)、胃线虫属种(Ostertagia spp.)、尖尾线虫属种(Oxyuris spp.)、Paracapillaria属种、副丝虫属种(Parafilaria spp.)、并殖吸虫属种(Paragonimus spp.)、同端盘吸虫属种(Paramphistomum spp.)、副裸头绦虫属种(Paranoplocephala spp.)、副蛔虫属种(Parascaris spp.)、栓尾线虫属种(Passalurus spp.)、原圆线虫属种(Protostrongylusspp.)、血吸虫属种(Schistosoma spp.)、腹腔丝虫属种(Setaria spp.)、旋毛线虫属种(Spirocerca spp.)、冠丝虫属种(Stephanofilaria spp.)、冠尾线属种(Stephanurusspp.)、粪圆线虫属种(Strongyloides spp.)、圆线虫属种(Strongylus spp.)、开口虫属种(Syngamus spp.)、绦虫属种(Taenia spp.)、背带线虫属种(Teladorsagia spp.)、吸吮线虫属种(Thelazia spp.)、弓蛔线虫属种(Toxascaris spp.)、弓蛔虫属种(Toxocaraspp.)、毛线虫属种(Trichinella spp.)、毛毕吸虫属种(Trichobilharzia spp.)、毛圆线虫属种(Trichostrongylus spp.)、鞭虫属种(Trichuris spp.)、钩虫属种(Uncinariaspp.)、吴策线虫属种(Wuchereria spp.);
来自线虫动物门的植物害虫,即植物寄生性线虫,尤其是野外垫刃属种(Aglenchus spp.),例如居农野外垫刃线虫(Aglenchus agricola);蛇线虫属种(Anguinaspp.),例如小麦粒瘿线虫(Anguina tritici);滑刃线虫属种(Aphelenchoides spp.),例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoidesfragariae);刺线虫属种(Belonolaimus spp.),例如Belonolaimus gracilis、芹刺线虫(Belonolaimus longicaudatus)、Belonolaimus nortoni;伞滑刃线虫属种(Bursaphelenchus spp.),例如椰子红环腐线虫(Bursaphelenchus cocophilus)、Bursaphelenchus eremus、松材线虫(Bursaphelenchus xylophilus);坏死线虫属种(Cacopaurus spp.),例如胡桃线虫(Cacopaurus pestis);小环线虫属种(Criconemellaspp.),例如弯曲小环线虫(Criconemella curvata)、Criconemella onoensis、装饰小环线虫(Criconemella ornata)、Criconemella rusium、异盘中环线虫(Criconemellaxenoplax)(=Mesocriconema xenoplax);轮线虫属种(Criconemoides spp.),例如Criconemoides ferniae、Criconemoides onoense、Criconemoides ornatum;茎线虫属种(Ditylenchus spp.),例如鳞球茎茎线虫(Ditylenchus dipsaci);锥线虫属种(Dolichodorus spp.);球异皮线虫属种(Globodera spp.),例如马铃薯白线虫(Globoderapallida)、马铃薯金线虫(Globodera rostochiensis);螺旋线虫属种(Helicotylenchusspp.),例如双宫螺旋线虫(Helicotylenchus dihystera);半轮线虫属种(Hemicriconemoides spp.);鞘线虫属种(Hemicycliophora spp.);异皮线虫属种(Heterodera spp.),例如燕麦异皮线虫(Heterodera avenae)、大豆胞囊线虫(Heteroderaglycines)、甜菜异皮线虫(Heterodera schachtii);纽带线虫属种(Hoplolaimus spp.);长针线虫属种(Longidorus spp.),例如Longidorus africanus;根结线虫属种(Meloidogyne spp.),例如哥伦比亚根结线虫(Meloidogyne chitwoodi)、Meloidogynefallax、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita);Meloinema属种;珍珠线虫属种(Nacobbus spp.);拟茎线虫属种(Neotylenchus spp.);拟滑刃线虫(Paraphelenchus spp.);拟毛刺线虫属种(Paratrichodorus spp.),例如微小拟毛刺线虫(Paratrichodorus minor);短体线虫属种(Pratylenchus spp.),例如穿刺短体线虫(Pratylenchus penetrans);Pseudohalenchus属种;Psilenchus属种;Punctodera属种;五沟线虫属种(Quinisulcius spp.);穿孔线虫属种(Radopholus spp.),例如柑橘穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis);肾状线虫属种(Rotylenchulus spp.);盘旋线虫属种(Rotylenchus spp.);盾线虫属种(Scutellonemaspp.);亚蛇形线虫属种(Subanguina spp.);轮胎虫属种(Trichodorus spp.),例如Trichodorus obtusus;原始毛刺线虫(Trichodorus primitivus);矮化线虫属种(Tylenchorhynchus spp.),例如饰环矮化线虫(Tylenchorhynchus annulatus);垫刃线虫属种(Tylenchulus spp.),例如半穿刺线虫(Tylenchulus semipenetrans);剑线虫属种(Xiphinema spp.),例如剑线虫(Xiphinema index)。
此外,还可以防治来自原生动物(Protozoa)亚界、球虫目(Coccidia)例如艾美球虫属种(Eimeria spp.)的害虫。
式(I)化合物还可任选地以特定浓度或施用率下用作除草剂、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(包括抵抗类病毒的试剂)或用作抗MLO(支原体样生物体)和RLO(立克次氏体样生物体)的试剂。如果合适,它们还可用作合成其他活性成分的中间体或前体。
制剂
本发明还涉及作为农药的制剂和由其制备的使用形式,例如浸液、滴液和喷液,其包含至少一种式(I)化合物。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鏻盐,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,例如铵肥、钾肥或磷肥。
常规制剂为例如水溶性液体(SL)、乳油(EC)、水乳剂(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);这些和其他可能的制剂类型例如被国际作物生命组织(Crop Life International)在以下文献中描述:农药说明书(Pesticide Specifications)、联合国粮农组织和世界卫生组织农药说明书开发与使用手册(Manual on development and use of FAO and WHO specifications forpesticides)、联合国粮农组织植物生产与保护文献-173(FAO Plant Production andProtection Papers–173)(由联合国粮农组织/世界卫生组织关于农药手册的联合会议制订,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成分。
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、扩散、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)化合物与助剂混合,所述助剂例如增量剂、溶剂和/或固体载体和/或其他助剂,例如,表面活性剂。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。
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)。
如果使用的增量剂为水,还可使用例如有机溶剂作为助溶剂。可用的液体溶剂主要为:芳族化合物,如二甲苯、甲苯或烷基萘;氯化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,例如石油馏分;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;氯化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、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,和粉碎的合成材料如细分散的二氧化硅、氧化铝和天然或合成的硅酸盐、树脂、蜡和/或固体肥料。同样可使用这些载体的混合物。可用的用于颗粒剂的载体包括:例如粉碎并分级的天然岩石,如方解石、大理石、浮石、海泡石、白云石,和无机和有机粉的合成颗粒,以及有机材料如锯屑、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包括聚丙烯酸盐;木素磺酸盐;苯酚磺酸盐或萘磺酸盐;环氧乙烷与脂肪醇或与脂肪酸或与脂肪胺、与取代的酚(优选烷基酚或芳基酚)的缩聚物;磺基琥珀酸酯的盐;牛磺酸衍生物(优选牛磺酸烷基酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯;以及含有硫酸酯、磺酸酯和磷酸酯的化合物的衍生物,例如烷基芳基聚乙二醇醚、烷基磺酸酯、烷基硫酸酯、芳基磺酸酯、蛋白质水解物、木素亚硫酸盐废液和甲基纤维素。如果式(I)的化合物之一和/或惰性病媒之一不溶于水并且如果在水中进行施用,则表面活性剂的存在是有利的。
可存在于制剂及由其衍生的使用形式中的其他助剂包括:染料,如无机颜料,例如氧化铁、氧化钛和普鲁士蓝,和有机染料如茜素染料、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(foam generator)或消泡剂。
此外,所述制剂和由其衍生的使用形式还可包含以下物质作为其他助剂:增粘剂(sticker),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,所述制剂和由其衍生的使用形式中可存在其他助剂。这类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、多价螯合剂(sequestrants)、络合剂、保湿剂、展着剂。通常,式(I)的化合物可与常用于制剂目的的任何固体或液体添加剂结合。
可用的保持促进剂包括降低动态表面张力的所有那些物质,例如磺基琥珀酸二辛酯,或提高粘弹性的所有那些物质,例如羟丙基瓜尔胶聚合物。
在本文中,合适的渗透剂为常用于促进农业化学活性化合物向植物渗透的所有那些物质。在本文中,由其从(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成分在表皮中迁移的能力来定义渗透剂。可使用文献(Baur等,1997,PesticideScience 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/或鏻盐,例如硫酸铵或磷酸氢二铵。
所述制剂优选包含0.00000001重量%至98重量%的式(I)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,基于制剂的重量计。
由所述制剂制得的使用形式(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)化合物的浓度通常可为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。施用以适合于使用形式的常规方式完成。
混合物
式(I)化合物还可作为与一种或多种合适的杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物剂(microbiologicals)、有益物种(beneficialspecies)、除草剂、肥料、鸟驱避剂、phytotonics、止繁殖剂、安全剂、信息化学物质和/或植物生长调节剂的混合物使用,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,这种类型的活性化合物的组合可改善植物生长和/或提高对非生物因子(例如高温或低温)、干旱或增加的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、提高采收物的品质和/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)化合物也可以与改善植物特性例如生长、产量和采收物的品质的试剂的混合物的形式使用。
在本发明的具体实施方案中,在制剂或由这些制剂制备的使用形式中,式(I)化合物以与其他化合物——优选下文所述的那些——的混合物的形式存在。
如果下述化合物中的某种化合物可存在不同互变异构形式,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。
杀昆虫剂/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”,第16版,British Crop Protection Concil2012)中或可在互联网(例如http://www.alanwood.net/pesticides)上搜索。
(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)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏/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(parathion)、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(cyfluthrin)、β-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(cyphenothrin)[(1R)-反式异构体]、溴氰菊酯(deltamethrin)、右旋烯炔菊酯(empenthrin)[(EZ)-(1R)异构体]、杀灭阿菊酯(esfenvalerate)、依芬普司(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)、扑灭司林(permethrin)、苯氧司林(phenothrin)[(1R)-反式异构体]、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(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)氯化物通道激活剂类,例如阿凡曼菌素(avermectins)/米尔倍霉素类(milbemycins),例如阿巴克丁(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectinbenzoate)、雷皮菌素(lepimectin)和弥拜菌素(milbemectin)。
(7)保幼激素模拟物,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)具有未知的或不明确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);或快螨特(propargite);或四氯杀螨砜(tetradifon)。
(13)间断H质子梯度的氧化磷酸化解偶联剂类,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)、二氟苯隆(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氯芬奴隆(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,环丙马秦(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,例如阿米曲士(amitraz)。
(20)复合物-III电子传递抑制剂类,例如氟蚁腙(hydramethylnon);或灭螨醌(acequinocyl);或嘧螨酯(fluacrypyrim)。
(21)复合物-I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)(鱼藤属(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)乙酰辅酶A羧化酶抑制剂类,例如特窗酸和特特拉姆酸衍生物,例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)和螺虫乙酯(spirotetramat)。
(24)复合物-IV电子传递抑制剂类,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电子传递抑制剂类,例如唑螨氰(cyenopyrafen)和丁氟螨酯(cyflumetofen)。
(28)兰尼碱(ryanodine)受体效应物(effector)类,例如二酰胺,例如氯虫酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)和氟虫酰胺(flubendiamide),
其他活性成分,例如afidopyropen、印楝素(azadirachtin)、benclothiaz、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、灭螨锰(quinomethionate)、冰晶石、
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;以及基于坚强芽孢杆菌(Bacillus firmus)(I-1582,BioNeem,Votivo)的制剂,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-甲基肼羧酸甲酯(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-乙基肼羧酸甲酯(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-甲基肼羧酸甲酯(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-乙基肼羧酸甲酯(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-氧化硫杂环丁烷基(oxidothietan)-3-基)苯甲酰胺(由WO2009/080250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-氧化硫杂环丁烷基-3-基)苯甲酰胺(WO2012/029672)、1-[(2-氯-1,3-噻唑-5-基)甲基]-4-氧代-3-苯基-4H-吡啶并[1,2-a]嘧啶-1-鎓-2-醇盐(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-醇盐(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)4-十二烷基-2,6-二甲基吗啉(aldimorph)、(1.2)(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(dodemorphacetate)、(1.12)(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)呋醚唑(furconazole-cis)、(1.25)己唑醇(hexaconazole)、(1.26)抑霉唑(imazalil)、(1.27)烯菌灵(imazalil sulphate)、(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-羧酸甲酯、(1.62)N'-{5-(二氟甲基)-2-甲基-4-[3-(三甲基甲硅烷基)丙氧基]苯基}-N-乙基-N-甲基酰亚胺基甲酰胺、(1.63)N-乙基-N-甲基-N'-{2-甲基-5-(三氟甲基)-4-[3-(三甲基甲硅烷基)丙氧基]苯基}酰亚胺基甲酰胺和(1.64)O-[1-(4-甲氧基苯氧基)-3,3-二甲基丁-2-基]-1H-咪唑-1-硫代羧酸酯、(1.65)啶菌噁唑(pyrisoxazole)。
(2)呼吸抑制剂(呼吸链抑制剂),例如(2.1)联苯吡菌胺(bixafen)、(2.2)啶酰菌胺(boscalid)、(2.3)萎锈灵(carboxin)、(2.4)二氟林(diflumetorim)、(2.5)甲呋酰胺(fenfuram)、(2.6)氟吡菌酰胺(fluopyram)、(2.7)氟酰胺(flutolanil)、(2.8)氟唑菌酰胺(fluxapyroxad)、(2.9)呋吡菌胺(furametpyr)、(2.10)拌种胺(furmecyclox)、(2.11)吡唑萘菌胺(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)戊苯吡菌胺(penflufen)、(2.21)吡噻菌胺(penthiopyrad)、(2.22)氟唑环菌胺(sedaxane)、(2.23)噻氟菌胺(thifluzamide)、(2.24)1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-3-(三氟甲基)-1H-吡唑-4-甲酰胺、(2.25)3-(二氟甲基)-1-甲基-N-[2-(1,1,2,2-四氟乙氧基)苯基]-1H-吡唑-4-甲酰胺、(2.26)3-(二氟甲基)-N-[4-氟-2-(1,1,2,3,3,3-六氟丙氧基)苯基]-1-甲基-1H-吡唑-4-甲酰胺、(2.27)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.28)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.29)苯并烯氟菌唑(benzovindiflupyr)、(2.30)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-桥亚甲基萘-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-1H-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)、(3.7)醚菌胺(dimoxystrobin)、(3.8)烯肟菌酯(enestroburin)、(3.9)噁唑菌酮(famoxadone)、(3.10)咪唑菌酮(fenamidone)、(3.11)氟菌螨酯(flufenoxystrobin)、(3.12)氟嘧菌酯(fluoxastrobin)、(3.13)醚菌酯(kresoxim-methyl)、(3.14)苯氧菌胺(metominostrobin)、(3.15)肟醚菌胺(orysastrobin)、(3.16)啶氧菌酯(picoxystrobin)、(3.17)唑菌胺酯(pyraclostrobin)、(3.18)唑胺菌酯(pyrametostrobin)、(3.19)唑菌酯(pyraoxystrobin)、(3.20)吡菌苯威(pyribencarb)、(3.21)氯啶菌酯(triclopyricarb)、(3.22)肟菌酯(trifloxystrobin)、(3.23)(2E)-2-(2-{[6-(3-氯-2-甲基苯氧基)-5-氟嘧啶-4-基]氧基}苯基)-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.24)(2E)-2-(甲氧基亚氨基)-N-甲基-2-(2-{[({(1E)-1-[3-(三氟甲基)苯基]亚乙基}氨基)氧基]甲基}苯基)乙酰胺、(3.25)(2E)-2-(甲氧基亚氨基)-N-甲基-2-{2-[(E)-({1-[3-(三氟甲基)苯基]乙氧基}亚氨基)甲基]苯基}乙酰胺、(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基次乙基]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)苯咪唑菌(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)抗病诱导剂(Resistance inducers),例如(6.1)苯并噻二唑(acibenzolar-S-methyl)、(6.2)异噻菌胺(isotianil)、(6.3)烯丙苯噻唑(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)霜霉灭(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)碘代丙炔基丁基甲胺酸酯(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(propamocarbhydrochloride)、(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)柯罗泽尔昆(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)苯噻清(benthiazole)、(15.2)嗪(bethoxazin)、(15.3)卡巴西霉素(capsimycin)、(15.4)香芹酮(carvone)、(15.5)灭螨猛(quinomethionate)、(15.6)甲氧苯啶菌(pyriofenone)(氯芬酮(chlazafenone))、(15.7)硫杂灵(cufraneb)、(15.8)环氟菌胺(cyflufenamid)、(15.9)霜脲氰(cymoxanil)、(15.10)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)氟氯菌核利(fluorimid)、(15.22)磺菌胺(flusulfamide)、(15.23)氟噻菌灵(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)人间霉素(irumamycin)、(15.29)磺菌威(methasulfocarb)、(15.30)异硫氰酸甲酯(methyl isothiocyanate)、(15.31)苯菌酮(metrafenone)、(15.32)米多霉素(mildiomycin)、(15.33)纳他霉素(natamycin)、(15.34)福美镍(nickel dimethyldithiocarbamate)、(15.35)酞菌酯(nitrothal-isopropyl)、(15.36)辛噻酮(octhilinone)、(15.37)奥克斯莫卡宾(oxamocarb)、(15.38)奥施康定(oxyfenthiin)、(15.39)五氯苯酚(pentachlorophenol)及其盐、(15.40)苯氧司林(phenothrin)、(15.41)磷酸及其盐、(15.42)霜霉威乙膦酸盐(propamocarb-fosetylate)、(15.43)丙烷辛钠(propanosine-sodium)、(15.44)丁吡吗啉(pyrimorph)、(15.45)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(15.46)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(15.47)吡咯尼林(pyrrolnitrin)、(15.48)异丁乙氧喹啉(tebufloquin)、(15.49)叶枯酞(tecloftalam)、(15.50)甲磺菌胺(tolnifanide)、(15.51)咪唑嗪(triazoxide)、(15.52)水杨菌胺(trichlamide)、(15.53)氰菌胺(zarilamid)、(15.54)(3S,6S,7R,8R)-8-苄基-3-[({3-[(异丁酰氧基)甲氧基]-4-甲氧基吡啶-2-基}羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧壬-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-羧酸酯、(15.59)2,3,5,6-四氯-4-(甲基磺酰基)吡啶、(15.60)2,3-二丁基-6-氯噻吩并[2,3-d]嘧啶-4(3H)-酮、(15.61)2,6-二甲基-1H,5H-[1,4]二噻英并[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-甲基酰亚胺基甲酰胺、(15.79)N-(4-氯苄基)-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.80)N-[(4-氯苯基)(氰基)甲基]-3-[3-甲氧基-4-(丙-2-炔-1-基氧基)苯基]丙酰胺、(15.81)N-[(5-溴-3-氯吡啶-2-基)甲基]-2,4-二氯烟酰胺、(15.82)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2,4-二氯烟酰胺、(15.83)N-[1-(5-溴-3-氯吡啶-2-基)乙基]-2-氟-4-碘烟酰胺、(15.84)N-{(E)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.85)N-{(Z)-[(环丙基甲氧基)亚氨基][6-(二氟甲氧基)-2,3-二氟苯基]甲基}-2-苯基乙酰胺、(15.86)N'-{4-[(3-叔丁基-4-氰基-1,2-噻唑-5-基)氧基]-2-氯-5-甲基苯基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.87)N-甲基-2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-N-(1,2,3,4-四氢萘-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-羧酸、(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]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-甲基酰亚胺基甲酰胺、(15.152)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.153)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.154)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.155)N'-{5-溴-6-[(顺式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.156)N'-{5-溴-6-[(反式-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.157)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.158)N-环丙基-N-(2-环丙基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.159)N-(2-叔丁基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.160)N-(5-氯-2-乙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.161)N-(5-氯-2-异丙基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.162)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-氟苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.163)N-环丙基-3-(二氟甲基)-5-氟-N-(5-氟-2-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.164)N-环丙基-N-(2-环丙基-5-氟苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.165)N-(2-环戊基-5-氟苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.166)N-环丙基-3-(二氟甲基)-5-氟-N-(2-氟-6-异丙基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.167)N-环丙基-3-(二氟甲基)-N-(2-乙基-5-甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.168)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基-5-甲基苄基)-1-甲基-1H-吡唑-4-甲酰胺、(15.169)N-环丙基-N-(2-环丙基-5-甲基苄基)-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.170)N-(2-叔丁基-5-甲基苄基)-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.171)N-[5-氯-2-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.172)N-环丙基-3-(二氟甲基)-5-氟-1-甲基-N-[5-甲基-2-(三氟甲基)苄基]-1H-吡唑-4-甲酰胺、(15.173)N-[2-氯-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.174)N-[3-氯-2-氟-6-(三氟甲基)苄基]-N-环丙基-3-(二氟甲基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.175)N-环丙基-3-(二氟甲基)-N-(2-乙基-4,5-二甲基苄基)-5-氟-1-甲基-1H-吡唑-4-甲酰胺、(15.176)N-环丙基-3-(二氟甲基)-5-氟-N-(2-异丙基苄基)-1-甲基-1H-吡唑-4-硫代甲酰胺、(15.177)3-(二氟甲基)-N-(7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1-甲基-1H-吡唑-4-甲酰胺、(15.178)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.179)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(15.180)N'-(2,5-二甲基-4-苯氧基苯基)-N-乙基-N-甲基酰亚胺基甲酰胺、(15.181)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基酰亚胺基甲酰胺、(15.182)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。根据具体情况,(1)至(15)类中提及的所有混合成分可与合适的碱或酸形成盐,只要它们基于其官能团能形成盐。
生物农药作为混合组分
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,如形成孢子的细菌、根部定殖细菌和起生物杀昆虫剂、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(DSM231179),或蜡状芽孢杆菌(Bacillus cereus),特别是蜡样芽孢杆菌菌株CNCM I-1562或坚强芽孢杆菌,菌株I-1582(登录号(Accession Number)CNCM I-1582)或短小芽孢杆菌(Bacilluspumilus),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(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,特别是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌库尔斯塔克亚种菌株HD-1,或苏云金芽孢杆菌拟步行甲亚种菌株NB 176(SD-5428),穿刺芽孢杆菌(Pasteuria penetrans),巴斯德氏芽菌属种(Pasteuria spp.)(肾形线虫(Rotylenchulus reniformis nematode))-PR3(登录号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);蜡蚧菌属种(Lecanicillium spp.),特别是菌株HRO LEC12;蜡蚧轮枝菌(Lecanicillium lecanii),(以前称为Verticillium lecanii),特别是菌株KV01;绿僵菌(Metarhizium anisopliae),特别是菌株F52(DSM3884/ATCC 90448);核果梅奇酵母菌(Metschnikowia fructicola),特别是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现为:Isariafumosorosea),特别是菌株IFPC 200613或菌株Apopka97(登录号ATCC 20874);淡紫色拟青霉(Paecilomyces lilacinus),特别是淡紫色拟青霉菌株251(AGAL 89/030550);黄蓝状菌(Talaromyces flavus),特别是菌株V117b;深绿木霉(Trichoderma atroviride),特别是菌株SC1(登录号CBS 122089);哈茨木霉(Trichoderma harzianum),特别是哈茨木霉rifaiT39(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”加入植物或植物部位或植物器官并借助其特殊的性质来促进植物生长和植物健康的细菌和真菌。实例包括:
土壤杆菌属种(Agrobacterium spp.);茎瘤固氮根瘤菌(Azorhizobiumcaulinodans);固氮螺菌属种(Azospirillum spp.)、固氮菌属种(Azotobacter spp.);短根瘤菌属种(Bradyrhizobium spp.);伯霍尔德杆菌属种(Burkholderia spp.),特别是洋葱伯霍尔德杆菌(Burkholderia cepacia)(以前称为洋葱假单胞菌(Pseudomonascepacia));巨孢囊霉属种(Gigaspora spp.),或单孢巨孢囊霉(Gigaspora monosporum);球囊霉属种(Glomus spp.);蜡蘑属种(Laccaria spp.);布氏乳杆菌(Lactobacillusbuchneri);类球囊霉属种(Paraglomus spp.);Pisolithus tinctorus;假单胞菌属种(Pseudomonas spp.);根瘤菌属种(Rhizobium spp.),尤其是三叶草根瘤菌(Rhizobiumtrifolii);须腹菌属种(Rhizopogon spp.);硬皮马勃属种(Scleroderma spp.);乳牛杆菌属种(Suillus spp.);链霉菌属种(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白质和次级代谢产物)的实例为:
大蒜(Allium sativum);苦艾(Artemisia absinthium);印楝素(azadirachtin);Biokeeper WP;Cassia nigricans;苦皮藤素(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);苦木(Quassiaamara);栎属(Quercus);皂树(Quillaja);Regalia;“RequiemTM杀昆虫剂”;鱼藤酮(rotenone);鱼尼丁(ryania)/兰尼碱(ryanodine);聚合草(Symphytum officinale);菊蒿(Tanacetum vulgare);百里香酚(thymol);Triact 70;TriCon;Tropaeulum majus;大荨麻(Urtica dioica);藜芦碱(Veratrin);白槲寄生(Viscum album);十字花科(Brassicaceae)提取物,尤其是油菜粉末或芥末粉。
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)、解草酯(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、2-甲氧基-N-({4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS 71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(CAS 52836-31-4)。
植物和植物部位
根据本发明可处理所有的植物和植物部位。在本文中,植物理解为意指所有的植物和植物种群,例如需要的和不需要的野生植物或作物植物(包括天然存在的作物植物),例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、番茄、豌豆和其他蔬菜品种、棉花、烟草、油菜以及水果植物(果实为苹果、梨、柑橘类水果和葡萄)。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受植物育种者权利保护的植物栽培种。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,以及根、块茎及根茎。植物部位还包括采收材料、以及无性与有性繁殖材料,例如插条、块茎、根茎、幼枝(slips)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通过常规处理方法直接进行或使所述化合物作用于其环境、生境或贮存空间而进行,所述常规处理方法例如浸渍、喷雾、蒸发、弥雾(fogging)、散布(scattering)、涂抹、注入,并且在繁殖材料的情况下,特别是种子的情况下,还可施用一层或多层包衣。
如上所提及,根据本发明可处理所有植物及其部位。在优选的实施方案中,处理野生植物种和植物栽培种,或由常规生物育种方法如杂交或原生质体融合而得到的那些,及其部位。在另一个优选的实施方案中,处理通过基因工程方法——如果合适与常规方法相结合——而得到的转基因植物和植物栽培种(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。根据本发明特别优选处理分别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通过常规育种、诱变或重组DNA技术获得的具有新特性(“性状”)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
根据本发明优选的待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、对高温或低温提高的耐受性、对干旱或对水或土壤盐度水平提高的耐受性、增强的开花性能、使采收更容易、加速成熟、更高的产量、使采收物的品质更高和/或营养价值更高、使采收物的贮存寿命更长和/或可加工性更好。这些特性的其他的、特别强调的实例为:由于例如在植物体内形成的毒素、特别是通过来自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)在植物体内形成的毒素而提高的植物对动物害虫和微生物有害物的抵抗力,例如对昆虫、蛛形纲动物、线虫、螨虫、蛞蝓和蜗牛的抵抗力;以及例如通过系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子(elicitor)和抗性基因以及相应地表达的蛋白质和毒素而导致的植物对植物致病真菌、细菌和/或病毒提高的抵抗力;以及植物对某些活性除草成分例如咪唑啉酮、磺酰脲、草甘膦或草丁膦(phosphinothricin)提高的耐受性(例如“PAT”基因)。赋予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。转基因植物的实例包括重要的作物植物,例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、甜菜、甘蔗、西红柿、豌豆和其他蔬菜品种、棉花、烟草、油菜以及水果植物(果实为苹果、梨、柑橘类水果和葡萄),特别强调的是玉米、大豆、小麦、稻、马铃薯、棉花、甘蔗、烟草和油菜。特别强调的性状为植物对昆虫、蜘蛛、线虫以及蛞蝓和蜗牛的提高的抵抗力。
作物保护——处理方式
使用式(I)化合物对植物和植物部位的处理是直接进行或通过作用于其环境、生境或储存空间而进行的,所述处理使用常规处理方法,例如通过浸渍、喷雾、雾化、灌溉、蒸发、撒粉、弥雾、撒播、发泡、涂抹、铺展(spreading-on)、注入、浇水(浸透)、滴灌,并且如果是处理繁殖材料,特别是如果是种子,还以粉末的形式用于干燥种子的处理、以溶液的形式用于液体种子的处理、以水溶性粉末的形式用于浆的处理,通过成包壳(incrusting),通过用一层或多层包衣包覆等。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。
优选植物的直接处理是叶施用,即将式(I)化合物施用于叶子,其中应当根据所讨论的害虫的侵染水平来调整处理频率和施用率。
在内吸收的活性化合物的情况下,式(I)化合物也可通过根系统到达植物。因此通过使式(I)化合物作用于植物的生境来处理植物。这可以例如通过以下方式来完成:浸透;混入土壤或营养液中,意指用式(I)化合物的液体形式浸渍植物的位置(例如土壤或水培体系);或土壤施用,意指将固体形式(例如以颗粒剂的形式)的式(I)化合物引入至植物的位置。在水稻作物的情况下,这也可通过将固体施用形式(例如以颗粒剂的形式)的式(I)化合物计量加入到淹没的(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害虫是早就已知的,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,所述方法在植物的储存过程中、播种后或出苗后免除、或至少显著地减少额外的农药施用。此外,期望优化使用的活性成分的量,从而为种子和发芽植物提供最佳保护,使其免受动物害虫的侵袭,而使用的活性成分不会损害植物本身。特别地,为了使用最少量的农药实现对种子和发芽植物的最佳保护,处理种子的方法还应考虑抵抗或耐受害虫的转基因植物固有的杀昆虫或杀线虫的特性。
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害虫侵袭的方法。本发明的用于保护种子和发芽植物免受害虫侵袭的方法还包括这样一种方法:其中种子用式(I)化合物和混合组分在一次操作中同时处理或依序处理。其还包括这样一种方法:其中种子用式(I)化合物和混合组分在不同时间处理。
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害虫侵袭的用途。
本发明还涉及已用式(I)化合物处理以免受动物害虫侵袭的种子。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的种子。在已用式(I)化合物和混合组分在不同时间处理的种子的情况下,单个物质可以不同层存在于种子上。在此情况下,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:其中式(I)化合物和混合组分作为包衣的一部分或作为除包衣之外的另一层或另几层而被施用。
本发明还涉及这样的种子:在用式(I)化合物处理之后,对其进行薄膜涂覆工艺以防止灰尘对种子的磨损。
内吸收作用的式(I)化合物的优点之一在于,通过处理种子,种子本身和由其所得的植物在出苗后皆受到保护以免受动物害虫的侵袭。这样,可无需在播种时或其后短时间内对作物立即进行处理。
另一优点是用式(I)化合物处理种子可促进被处理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更好地定植,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。更具体而言,包括以下植物的种子:谷物(例如,小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、稻、马铃薯、向日葵、咖啡、烟草、芸苔(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)、水果植物、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、芸苔、油菜和稻的种子。
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。这涉及通常包含至少一种异源基因的植物的种子,所述异源基因控制特别是具有杀昆虫和/或杀线虫特性的多肽的表达。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)或者胶霉属(Gliocladium)。本发明特别适于处理包含至少一种源自芽孢杆菌属种(Bacillus sp)的异源基因的转基因种子。所述异源基因更优选源自苏云金芽孢杆菌。
在本发明的上下文中,将(I)化合物施用于种子。优选在种子足够稳定以在处理过程中不发生损伤的状态下处理种子。通常,可在采收和播种之间的任何时间处理种子。通常使用已从植物中分离并且已除去穗轴、外壳、茎、外壳、毛或果肉的种子。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。如果是稻的种子,也可以使用例如已吸收水直到达到特定阶段(鸡胸(pigeon breast)阶段)的种子,这改善了发芽情况并使出苗更均匀。
当处理种子时,通常必须注意选择施用于种子的式(I)化合物的量和/或其他添加剂的量,以使种子的发芽不受到不利影响,或必须注意不使所得的植物受到损害。对于在特定施用率下可表现出植物毒性作用的活性成分,必须特别确保这一点。
通常,将式(I)的化合物以合适的制剂形式施用至种子。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、浆液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用化学成分的制剂的所有物质。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合适的分散剂和/或乳化剂为常规用于活性农用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具体包括环氧乙烷/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/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用化学化合物的制剂的所有抑制泡沫的物质。可优选使用有机硅消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为在农用化学组合物中可用于此目的的所有物质。实例包括双氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为在农用化学组合物中可用于此目的的所有物质。优选的实例包括纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的有用的胶粘剂包括可用于拌种产品中的所有常规粘合剂。优选的实例包括聚乙烯吡咯烷酮、聚乙酸乙烯基酯、聚乙烯醇和甲基纤维素。
可存在于可根据本发明使用的拌种制剂中的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。赤霉素是已知的(参见R.Wegler“Chemie derPflanzenschutz-und”,第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可以直接或在先用水稀释后用于处理各种不同种类的种子。例如,浓缩剂或可通过用水稀释而由其获得的制剂可用于对以下种子进行拌种:谷物如小麦、大麦、黑麦、燕麦和黑小麦的种子,以及玉米、稻、油菜、豌豆、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:将种子分批或以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。施用率由制剂中的式(I)化合物的具体含量和种子决定。式(I)化合物的施用率通常为0.001-50g/kg种子,优选0.01-15g/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有抵抗活性。术语“内寄生虫”尤其包括蠕虫和原生动物,如球虫目(coccidia)。外寄生虫通常优选为节肢动物,尤其是昆虫和螨类。
在兽医领域,对温血物种具有有利的毒性的式(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有抵抗活性。
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;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。
在一个优选实施方案中,将式(I)化合物给予哺乳动物。
在另一个优选实施方案中,将式(I)化合物给予鸟类,即笼鸟,以及特别是家禽。
使用式(I)化合物来防治动物寄生虫旨在减少或预防疾病、死亡病例和性能下降(在肉、奶、羊毛、皮、蛋、蜜等的情况下),从而使得动物饲养更经济、更简单,并可实现更好的动物健康。
关于动物健康领域,术语“防治(control或controlling)”意指式(I)化合物有效地将特定寄生虫在被这类寄生虫感染的动物中的的发病率降低至无害的程度。更具体而言,本文中的“防治”意指式(I)化合物可杀死各寄生虫、抑制其生长或抑制其增殖。
节肢动物包括:
虱目(Anoplurida),例如血虱属种(Haematopinus spp.)、毛虱属种(Linognathusspp.)、虱属种(Pediculus spp.)、阴风属种(Phtirus spp.)、管虱属种(Solenopotesspp.);食毛目(Mallophagida)和钝角亚目(Amblycerina)和细角亚目(Ischnocerina),例如毛羽虱属种(Trimenopon spp.)、禽虱属种(Menopon spp.)、巨羽虱属种(Trinotonspp.)、牛羽虱属种(Bovicola spp.)、Werneckiella属种、Lepikentron属种、畜虱属种(Damalina spp.)、嚼虱属种(Trichodectes spp.)、猫羽虱属种(Felicola spp.);双翅目(Diptera)和长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属种(Aedesspp.)、按蚊属种(Anopheles spp.)、库蚊属种(Culex spp.)、蚋属种(Simulium spp.)、真蚋属种(Eusimulium spp.)、白蛉属种(Phlebotomus spp.)、罗蛉属种(Lutzomyia spp.)、库蠓属种(Culicoides spp.)、斑虻属种(Chrysops spp.)、短蚋亚属种(Odagmia spp.)、维蚋亚属种(Wilhelmia spp.)、瘤虻属种(Hybomitra spp.)、黄虻属种(Atylotus spp.)、虻属种(Tabanus spp.)、麻虻属种(Haematopota spp.)、Philipomyia属种、蜂虱蝇属种(Braula spp.)、家蝇属种(Musca spp.)、齿股蝇属种(Hydrotaea spp.)、螫蝇属种(Stomoxys spp.)、黑角蝇属种(Haematobia spp.)、莫蝇属种(Morellia spp.)、厕蝇属种(Fannia spp.)、舌蝇属种(Glossina spp.)、丽蝇属种(Calliphora spp.)、绿蝇属种(Lucilia spp.)、金蝇属种(Chrysomyia spp.)、污蝇属种(Wohlfahrtia spp.)、麻蝇属种(Sarcophaga spp.)、狂蝇属种(Oestrus spp.)、皮蝇属种(Hypoderma spp.)、胃蝇属种(Gasterophilus spp.)、虱蝇属种(Hippobosca spp.)、羊虱蝇属种(Lipoptena spp.)、蜱蝇属种(Melophagus spp.)、鼻狂蝇属种(Rhinoestrus spp.)、大蚊属种(Tipula spp.);蚤目(Siphonapterida),例如蚤属种(Pulex spp.)、栉头蚤属种(Ctenocephalides spp.)、潜蚤属种(Tunga spp.)、客蚤属种(Xenopsylla spp.)、角叶蚤属种(Ceratophyllus spp.);
异翅目(Heteropterida),例如臭虫属种(Cimex spp.)、锥猎蝽属种(Triatomaspp.)、红猎蝽属种(Rhodnius spp.)、锥蝽属种(Panstrongylus spp.);以及来自蜚蠊目(Blattarida)的公害害虫和卫生害虫。
节肢动物还包括:
蜱螨亚纲(Acari)(蜱螨目(Acarina))和后气门目(Metastigmata),例如软蜱科(Argasidae),如锐缘蜱属种(Argas spp.)、钝缘蜱属种(Ornithodorus spp.)、残喙蜱属种(Otobius spp.);硬蜱科(Ixodidae),如硬蜱属种(Ixodes spp.)、花蜱属种(Amblyommaspp.)、扇头蜱属(牛蜱属)种(Rhipicephalus(Boophilus)spp.)、革蜱属种(Dermacentorspp.)、血蜱属种(Haemophysalis spp.)、璃眼蜱属种(Hyalomma spp.)、扇头蜱属种(Rhipicephalus spp.)(多宿主蜱的原始的属);中气门目(Mesostigmata),如皮刺螨属种(Dermanyssus spp.)、禽刺螨属种(Ornithonyssus spp.)、肺刺螨属种(Pneumonyssusspp.)、刺利螨属种(Raillietia spp.)、肺刺螨属种(Pneumonyssus spp.)、胸刺螨属种(Sternostoma spp.)、蜂螨属种(Varroa spp.)、蜂盾螨属种(Acarapis spp.);辐螨目(Actinedida)(前气门目(Prostigmata)),例如蜂盾螨属种(Acarapis spp.)、姬螯螨属种(Cheyletiella spp.)、禽螯螨属种(Ornithocheyletia spp.)、肉螨属种(Myobia spp.)、疮螨属种(Psorergates spp.)、蠕形螨属种(Demodex spp.)、恙螨属种(Trombiculaspp.)、Neotrombiculla属种、Listrophorus属种;和粉螨目(Acaridida)(无气门目(Astigmata)),例如粉螨属种(Acarus spp.)、食酪螨属种(Tyrophagus spp.)、嗜木螨属种(Caloglyphus spp.)、颈下螨属种(Hypodectes spp.)、翅螨属种(Pterolichus spp.)、痒螨属种(Psoroptes spp.)、皮螨属种(Chorioptes spp.)、耳疥螨属种(Otodectes spp.)、疥螨属种(Sarcoptes spp.)、耳螨属种(Notoedres spp.)、鸟疥螨属种(Knemidocoptesspp.)、气囊螨属种(Cytodites spp.)、鸡雏螨属种(Laminosioptes spp.)。
寄生性原生动物包括:
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),例如兰伯贾第虫(Giardia lamblia)、犬贾第虫(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);哈氏科(Hartmanellidae),例如,棘阿米巴属种(Acanthamoeba sp.)、哈氏属种(Harmanellasp.)。
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)、腺样艾美球虫(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)、青紫蓝兔艾美球虫(E.chinchillae)、鲱鱼艾美球虫(E.clupearum)、鸽艾美球虫(E.columbae)、弯曲艾美球虫(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)、椭圆艾美球虫(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)、勒氏艾美球虫(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)、锥艾美球虫(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)、格洛虫属种(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)、等孢子球虫属种(I.spec.)、猪等孢子球虫(I.suis)、囊等孢虫属种(Cystisospora spec.)、隐孢子虫属种(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(Toxoplasma gondii)、Hammondia heydornii、犬新孢子虫(Neospora caninum)、贝斯虫(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)、羊犬肉孢子虫(S.ovicanis)、羊猫肉孢子虫(S.ovifelis)、S.neurona、肉孢子虫属种(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(Plasmodiumberghei)、恶性疟原虫(P.falciparum)、三日疟原虫(P.malariae)、卵形疟原虫(P.ovale)、间日疟原虫(P.vivax),疟原虫属种(P.spec.),如梨质纲(Piroplasmea),例如阿根廷巴贝虫(Babesia argentina)、牛巴贝虫(B.bovis)、犬巴贝虫(B.canis)、巴贝虫属种(B.spec.)、小泰勒虫(Theileria parva),泰勒虫属种(Theileria spec.),如匿虫亚目(Adeleina),例如犬肝簇虫(Hepatozoon canis)、肝簇虫属种(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)。这些包括:
单殖亚纲:例如:三代虫属种(Gyrodactylus spp.)、指环虫(Dactylogyrusspp.)、多盘吸虫属种(Polystoma spp.)。
绦虫:假叶目(Pseudophyllidea),例如:裂头属种(Diphyllobothrium spp.)、迭宫绦虫属种(Spirometra spp.)、裂头绦虫属种(Schistocephalus spp.)、舌状绦虫属种(Ligula spp.)、吸叶绦虫属种(Bothridium spp.)、复殖孔绦虫属种(Diplogonoporusspp.)。
圆叶目(Cyclophyllidea),例如:中殖孔绦虫属种(Mesocestoides spp.)、裸头绦虫属种(Anoplocephala spp.)、副裸头绦虫属种(Paranoplocehala spp.)、蒙尼绦虫属种(Moniezia spp.)、繸体绦虫属种(Thysanosomsa spp.)、曲子宫绦虫属种(Thysanieziaspp.)、无卵黄腺绦虫属种(Avitellina spp.)、斯泰勒绦虫属种(Stilesia spp.)、鸣绦虫属种(Cittotaenia spp.)、Andyra属种、伯特绦虫属种(Bertiella spp.)、带绦虫属种(Taenia spp.)、棘球绦虫属种(Echinococcus spp.)、泡尾绦虫属种(Hydatigera spp.)、代凡绦虫属种(Davainea spp.)、瑞利绦虫属种(Raillietina spp.)、膜壳绦虫属种(Hymenolepis spp.)、棘鳞绦虫属种(Echinolepis spp.)、棘叶绦虫属种(Echinocotylespp.)、双睾绦虫属种(Diorchis spp.)、复孔绦虫属种(Dipylidium spp.)、约优克斯绦虫属种(Joyeuxiella spp.)、复孔绦虫属种(Diplopylidium spp.)。
吸虫:复殖亚纲(Digenea),例如:双穴吸虫属种(Diplostomum spp.)、茎双穴吸虫属种(Posthodiplostomum spp.)、血吸虫属种(Schistosoma spp.)、毛毕吸虫属种(Trichobilharzia spp.)、鸟毕吸虫属种(Ornithobilharzia spp.)、澳毕吸虫属种(Austrobilharzia spp.)、巨毕吸虫属种(Gigantobilharzia spp.)、彩蚴吸虫属种(Leucochloridium spp.)、短咽吸虫属种(Brachylaima spp.)、棘口吸虫属种(Echinostoma spp.)、棘缘吸虫属种(Echinoparyphium spp.)、棘隙吸虫属种(Echinochasmus spp.)、低颈吸虫属种(Hypoderaeum spp.)、片形吸虫属种(Fasciolaspp.)、片形吸虫属种(Fasciolides spp.)、姜片吸虫属种(Fasciolopsis spp.)、环腔吸虫属种(Cyclocoelum spp.)、盲腔吸虫属种(Typhlocoelum spp.)、同端盘吸虫属种(Paramphistomum spp.)、杯殖吸虫属种(Calicophoron spp.)、殖盘吸虫属种(Cotylophoron spp.)、巨盘吸虫属种(Gigantoctyle spp.)、菲策吸虫属种(Fischoederius spp.)、腹袋吸虫属种(Gastrothylacus spp.)、背孔吸虫属种(Notocotylus spp.)、下弯吸虫属种(Catatropis spp.)、斜睾吸虫属种(Plagiorchisspp.)、前殖吸虫属种(Prosthogonimus spp.)、双腔吸虫属种(Dicrocoelium spp.)、阔盘吸虫属种(Eurytema spp.)、鲑吸虫属种(Troglotrema spp.)、并殖吸虫属种(Paragonimusspp.)、表孔吸虫属种(Collyriclum spp.)、侏形吸虫属种(Nanophyetus spp.)、后睾吸虫属种(Opisthorchis spp.)、支睾吸虫属种(Clonorchis spp.)、次睾吸虫属种(Metorchisspp.)、异形吸虫属种(Heterophyes spp.)、后殖吸虫属种(Metagonimus spp.);
线虫:毛形科(Trichinellida),例如:鞭虫属种(Trichuris spp.)、毛细线虫属种(Capillaria spp.)、Paracapillaria属种、优鞘属种(Eucoleus spp.)、Trichomosoides属种、毛线虫属种(Trichinella spp.);
垫刃目(Tylenchida),例如:细丝鲶属种(Micronema spp.)、类圆线虫属种(Strongyloides spp.)。
杆形亚目(Rhabditina),例如:圆线虫属种(Strongylus spp.)、三齿属种(Triodontophorus spp.)、食道齿属种(Oesophagodontus spp.)、毛线属种(Trichonemaspp.)、辐首线虫属种(Gyalocephalus spp.)、柱咽属种(Cylindropharynx spp.)、杯口线虫属种(Poteriostomum spp.)、Cyclococercus属种、杯冠属种(Cylicostephanus spp.)、结节线虫属种(Oesophagostomum spp.)、夏柏特线虫属种(Chabertia spp.)、冠尾线属种(Stephanurus spp.)、钩口线虫属种(Ancylostoma spp.)、钩虫属种(Uncinaria spp.)、板口线虫属种(Necator spp.)、仰口线虫属种(Bunostomum spp.)、球头线虫属种(Globocephalus spp.)、开口虫属种(Syngamus spp.)、杯口属种(Cyathostoma spp.)、后圆线虫属种(Metastrongylus spp.)、网尾线虫属种(Dictyocaulus spp.)、缪勒线虫属种(Muellerius spp.)、原圆线虫属种(Protostrongylus spp.)、新圆线虫属种(Neostrongylus spp.)、囊尾线虫属种(Cystocaulus spp.)、肺圆属种(Pneumostrongylusspp.)、Spicocaulus属种、麂圆线虫属种(Elaphostrongylus spp.)、拟马鹿圆线虫属种(Parelaphostrongylus spp.)、环体线虫属种(Crenosoma spp.)、Paracrenosoma属种、奥斯勒线虫属种(Oslerus spp.)、管圆线虫属种(Angiostrongylus spp.)、猫圆线虫属种(Aelurostrongylus spp.)、类丝虫属种(Filaroides spp.)、副类丝虫属种(Parafilaroides spp.)、毛圆线虫属种(Trichostrongylus spp.)、血矛线虫属种(Haemonchus spp.)、胃线虫属种(Ostertagia spp.)、背带线虫属种(Teladorsagiaspp.)、马歇尔线虫属种(Marshallagia spp.)、古柏线虫属种(Cooperia spp.)、日圆线虫属种(Nippostrongylus spp.)、螺旋线虫属种(Heligmosomoides spp.)、细颈线虫属种(Nematodirus spp.)、猪圆线虫属种(Hyostrongylus spp.)、尖柱线虫属种(Obeliscoidesspp.)、裂口线虫属种(Amidostomum spp.)、沃鲁线虫属种(Ollulanus spp.);
旋尾目(Spirurida),例如:尖尾线虫属种(Oxyuris spp.)、蛲虫属种(Enterobiusspp.)、栓尾线虫属种(Passalurus spp.)、管状线虫属种(Syphacia spp.)、无刺线虫属种(Aspiculuris spp.)、异刺线虫属种(Heterakis spp.);蛔虫属种(Ascaris spp.)、弓蛔线虫属种(Toxascaris spp.)、弓蛔虫属种(Toxocara spp.)、贝利蛔线虫属种(Baylisascaris spp.)、副蛔虫属种(Parascaris spp.)、异尖线虫属种(Anisakis spp.)、鸡蛔虫属种(Ascaridia spp.);颚口线虫属种(Gnathostoma spp.)、泡翼线虫属种(Physaloptera spp.)、吸吮线虫属种(Thelazia spp.)、筒线虫属种(Gongylonema spp.)、丽线虫属种(Habronema spp.)、副柔线属种(Parabronema spp.)、德拉西线虫属种(Draschia spp.)、龙线虫属种(Dracunculus spp.);冠丝虫属种(Stephanofilariaspp.)、副丝虫属种(Parafilaria spp.)、腹腔丝虫属种(Setaria spp.)、罗阿丝虫属种(Loa spp.)、恶丝虫属种(Dirofilaria spp.)、光丝虫属种(Litomosoides spp.)、布鲁线虫属种(Brugia spp.)、吴策线虫属种(Wuchereria spp.)、盘尾丝虫属种(Onchocercaspp.)、旋毛线虫属种(Spirocerca spp.);
棘头虫纲(Acanthocephala):寡棘吻目(Oligacanthorhynchida),例如:巨吻棘头虫属种(Macracanthorhynchus spp.)、前睾棘头虫属种(Prosthenorchis spp.);多形目(Polymorphida),例如:细颈棘头虫属种(Filicollis spp.);念珠目(Moniliformida),例如:念珠棘虫属种(Moniliformis spp.);
棘吻目(Echinorhynchida),例如,棘头虫属种(Acanthocephalus spp.)、钩头虫属种(Echinorhynchus spp.)、似细吻棘头虫属种(Leptorhynchoides spp.)。
舌形动物门(Pentastoma):洞头虫目(Porocephalida),例如,舌形虫属种(Linguatula spp.)。
在兽医领域和动物饲养中,式(I)化合物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予。给予可为预防性的或治疗性的。
因此,本发明的一个实施方案涉及式(I)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。
反之,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昆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昆虫剂或杀螨剂的用途,例如用于动物畜牧业、动物饲养、动物笼舍或卫生领域中。
病媒的防治(vector control)
式(I)的化合物还可用于病媒的防治。在本发明的上下文中,病媒是能将病原体例如病毒、蠕虫、单细胞生物和细菌从贮主(reservoir)(植物、动物、人类等)传播到宿主的节肢动物,尤其是昆虫或蛛形纲动物。病原体可被机械地传播至宿主(例如沙眼通过无刺苍蝇传播)或在注入后被传播至宿主(例如通过蚊子传播的疟原虫)。
病媒和它们传播的疾病或病原体的实例为:
1)蚊子
-疟蚊:疟疾、丝虫病;
-库蚊:日本脑炎、丝虫病、其他病毒性疾病、蠕虫的传播;
-伊蚊:黄热病、登革热、丝虫病、其他病毒性疾病;
-蚋科:蠕虫的传播,特别是旋盘尾丝虫(Onchocerca volvulus);
2)虱子: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:螨病、流行性斑疹伤寒、立克次氏体痘、土拉菌病、圣路易斯型脑炎、蜱传脑炎(TBE)、克里米亚-刚果出血热(Crimean–Congo haemorrhagic fever)、包柔氏螺旋体病(borreliosis);
6)壁虱: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))。
在本发明的上下文中,病媒的实例为可将植物病毒传播至植物的昆虫,例如蚜虫、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。
在本发明的上下文中,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;螨虫和壁虱。
如果式(I)化合物具有抗突破性(resistance-breaking),则也可实现病媒防治。
式(I)化合物适用于预防通过病媒传播的疾病和/或病原体。因此,本发明的另一个方面为式(I)化合物用于病媒防治的用途,例如在农业、园艺、林业、花园和休闲设施中,以及在材料和储藏产品的保护中。
工业材料保护
式(I)化合物适合用于保护工业材料抵抗昆虫的攻击或破坏,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昆虫剂和/或至少一种杀真菌剂一起使用。
在另一个实施方案中,式(I)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而应用于所讨论的材料。特别地,合适的其他杀昆虫剂或杀真菌剂为上述那些。
出人意料地,还已发现,式(I)化合物可用于保护与海水或含盐水接触的物体以抵抗污损,特别是船体、筛、网、建筑物、系泊用具和信号系统。式(I)化合物也可以单独地或与其它活性成分结合地用作为防污剂。
卫生领域中动物害虫的防治
式(I)化合物适合用于防治卫生领域中的动物害虫。更具体而言,本发明可用于家用领域、卫生领域和储藏产品的保护中,特别是用于防治在封闭空间例如住所、工厂大厅、办公室、车辆舱室中遇到的昆虫、蛛形纲动物和螨。为了防治动物害虫,将式(I)化合物单独使用或与其他活性成分和/或助剂结合使用。它们优选用于家用杀昆虫剂产品中。式(I)化合物对抗敏感物种和抗性物种以及对抗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)。
以下列形式进行施用:例如,气雾剂、非加压喷雾产品,例如泵喷雾剂及雾化器喷雾剂;自动弥雾系统;烟雾发生器;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;推进器驱动的蒸发器;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。
方法和中间体的说明
下面的制备实施例和用途实施例说明本发明,而非限制本发明。产品通过1H NMR谱和/或LC/MS(液相色谱质谱联用)表征。
logP值按照OECD Guideline 117(EC Directive 92/69/EEC)通过HPLC(高效液相色谱法)使用反相(RP)柱(C18)由以下方法测定:
[a]酸性范围内的LC-MS测定用0.1%甲酸水溶液和乙腈(含有0.1%甲酸)作为洗脱剂在pH 2.7下进行;线性梯度为10%乙腈至95%乙腈。
[b]中性范围内的LC-MS测定用0.001摩尔的碳酸氢铵水溶液和乙腈作为洗脱剂在pH 7.8下进行;线性梯度为10%乙腈至95%乙腈。
用logP值已知的无支链的烷-2-酮(具有3至16个碳原子)进行校正(logP值基于保留时间通过两个连续烷酮之间的线性内插来确定)。
NMR谱使用安装有流动探头(体积60μl)的Bruker Avance 400进行测定。在个别情况下,NMR谱使用Bruker Avance II 600进行测量。
所选实例的NMR数据以常规形式(δ值、多重峰分裂、氢原子数目)列出。信号的分裂描述如下:s(单峰)、d(双峰)、t(三重峰)、q(四重峰)、quint(五重峰)、m(多重峰)、b(宽峰信号)。使用的溶剂是CD3CN、CDCl3或D6-DMSO,并使用四甲基硅烷(0.00ppm)作为参比物。
制备实施例
实施例1
5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-2-(吡啶-3-基)-2,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮(I-1-1)
步骤1:
3-氨基-N-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-1-(吡啶-3-基)-1H-吡唑-4-甲酰胺(II-1)
将2.09ml 2M三甲基铝的甲苯溶液缓慢滴加到于1.3ml 1,2-二氯乙烷中的500mg(2.09mmol)2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯胺中,并将混合物在室温下搅拌1小时(h)。将562mg(2.09mmol)3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)加到1.3ml 1,2-二氯乙烷中,并将反应混合物回流过夜。冷却后,将反应混合物用水稀释并小心地倾倒入至10%酒石酸钠钾溶液中。所述混合物通过振摇用二氯甲烷萃取三次,并将有机相取出,经硫酸钠干燥,过滤并浓缩。使残余物吸附到硅胶上并通过制备型MPLC在硅胶柱上纯化(流动相:环己烷/乙酸乙酯)。分离出的级分得到551mg(根据LC/MS纯度为100%,理论值的62%)的标题化合物。
logP[a]:2.72;logP[b]:2.63;1H NMR(D6-DMSO,400MHz)δppm:9.61(d,1H),9.05(s,1H),8.95(d,1H),8.49-8.48(m,1H),8.06-8.02(m,1H),7.91(d,1H),7.57-7.53(m,1H),7.29(d,1H),5.89(s,2H),3.85(q,2H),2.41(s,3H)
步骤2:
5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-2-(吡啶-3-基)-2,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮(I-1-1)
将34.0mg(0.20mmol)对甲苯磺酸和200μl(178mmol,1.20mmol)原甲酸三乙酯加入到于2ml N,N-二甲基乙酰胺中的170mg(0.40mmol)3-氨基-N-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-1-(吡啶-3-基)-1H-吡唑-4-甲酰胺(II-1)中。将反应混合物在CEMDiscover微波中在200瓦特下加热至130℃并保持1h。冷却后,将反应混合物与RP-18材料混合,并在减压下除去溶剂。将残余物通过制备型MPLC(流动相:水/乙腈)在RP-18柱上纯化。分离出的级分含有80.0mg(根据LC/MS纯度为96%,理论值的44%)的标题化合物。
logP[a]:2.65;logP[b]:2,63;1H NMR(D6-DMSO,400MHz)δppm:9.59(d,1H),9.29(s,1H),8.68(dd,1H),8.47-8.44(m,1H),8.36(s,1H),7.87(d,1H),7.68-7.64(m,1H),7.46(d,1H),4.03(q,2H),2.46(s,3H)
实施例2
3-[2-氟-4-甲基-5-(2,2,2-三氟乙基亚磺酰基)苯基]-6-(3-吡啶基)吡唑并[3,4-d]三嗪-4-酮(I-1-2)和3-[2-氟-4-甲基-5-(2,2,2-三氟乙基硫基)苯基]-6-(3-吡啶基)吡唑并[3,4-d]三嗪-4-酮(I-1-3)
将248mg(3.60mmol)亚硝酸钠于5ml水中的溶液滴加到于5ml水和5ml浓盐酸中的180mg(0.42mmol)3-氨基-N-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-1-(吡啶-3-基)-1H-吡唑-4-甲酰胺(II-1)中。将混合物在70℃下搅拌6小时。冷却后,将反应混合物倾倒入二氯甲烷中,并用浓碳酸氢钠溶液将pH调节至7。将混合物用二氯甲烷萃取三次,并将合并的有机相用水洗涤,用硫酸钠干燥,过滤并浓缩。将残余物吸附到RP-18上并通过制备型MPLC(流动相:水/乙腈)在RP-18柱上纯化。分离出的级分含有64.0mg(根据LC/MS纯度为100%,理论值的33%)的3-[2-氟-4-甲基-5-(2,2,2-三氟乙基亚磺酰基)苯基]-6-(3-吡啶基)吡唑并[3,4-d]三嗪-4-酮(I-1-2)和72.0mg(根据LC/MS纯度为100%,理论值的39%)的3-[2-氟-4-甲基-5-(2,2,2-三氟乙基硫基)苯基]-6-(3-吡啶基)吡唑并[3,4-d]三嗪-4-酮(I-1-3)。
(I-1-2)logP[a]:2.22;logP[b]:2.19;1H NMR(D6-DMSO,400MHz)δppm:9.84(s,1H),9.37(s,1H),9.36(d,1H),8.78-8.76(m,1H),8.20(d,1H),7.75-7.71(m,1H),7.64(d,1H),4.39-4.01(m,2H),3H在DMSO峰下。
(I-1-3)logP[a]:3.18;logP[b]:3.14;1H NMR(D6-DMSO,400MHz)δppm:9.84(s,1H),9.36(s,1H),8.78-8.76(m,1H),8.56-8.53(d,1H),7.95(d,1H),7.75-7.71(m,1H),7.52(d,1H),3.99(q,2H),3H在DMSO峰下。
实施例3
5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-2-(吡啶-3-基)-2,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮(I-1-4)
在0℃下将35.4mg(0.14mmol)间氯过苯甲酸加入到61.0mg(0.14mmol)5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-2-(吡啶-3-基)-2,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮(I-1-1)于3ml二氯甲烷的溶液中。将反应混合物在室温下搅拌2小时,然后用二氯甲烷稀释并用浓碳酸氢钠溶液处理。10分钟后,进行相分离,将有机相与RP-18材料混合,并在减压下除去溶剂。将残余物通过制备型MPLC(流动相:水/乙腈)在RP-18柱上纯化。分离出的级分含有36.0mg(根据LC/MS纯度为98.5%,理论值的56%)的标题化合物。
logP[a]:1.79;logP[b]:1,78;1H NMR(D6-DMSO,400MHz)δppm:9.60(s,1H),9.30(d,1H),8.68(d,1H),8.47-8.42(m,2H),8.11(d,1H),7.67-7.65(m,1H),7.58(d,1H),4.35-4.05(m,2H),3H在DMSO峰下。
实施例4
5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-2-(1-氧化吡啶(oxidopyridin)-1-鎓-3-基)吡唑并[3,4-d]嘧啶-4-酮(I-1-5)
在0℃下将119mg(0.48mmol)间氯过苯甲酸加入到100mg(0.23mmol)5-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)硫基]苯基}-2-(吡啶-3-基)-2,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮(I-1-1)于3ml二氯甲烷的溶液中。将反应混合物在室温下搅拌过夜,随后用28.0mg(0.12mmol)间氯过苯甲酸处理。在室温下再过一夜后,将反应混合物用二氯甲烷稀释并用浓碳酸氢钠溶液处理。10分钟后,将固体抽滤出,用水和二氯甲烷洗涤并干燥。固体中含有43.0mg(根据LC/MS纯度为78%,理论值的31%)的标题化合物。
logP[a]:1.39;logP[b]:1.33;1H NMR(D6-DMSO,400MHz)δppm:9.60(s,1H),9.02(s,1H),8.44(s,1H),8.31(d,1H),8.11(d,1H),8.03(d,1H),7.65-7.57(m,2H),4.32-4.05(m,2H),3H在DMSO峰下
中间体的合成
通过方法B合成5-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(IIIa-1)和3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)
首先将82.3g(0.59mol)碳酸钾加入到三口烧瓶中。在氩气下烘烤烧瓶,然后依次加入以下物质:2.70g(0.014mol)的碘化铜(I)、44.0g(0.28mol)的3-氨基-4-吡唑甲酸乙酯和440ml的N,N-二甲基乙酰胺。将悬浮液搅拌10分钟,然后加入7.18g(0.056mol)反式-1,2-二氨基环己烷和53.77g(0.34mol)3-溴吡啶。使反应混合物达到回流温度并在145℃下搅拌过夜。冷却后,抽吸滤出反应混合物,将母液浓缩并将残余物通过MPLC使用RP(C-18)柱用乙腈/水/0.1%甲酸进行纯化。根据LC/MS,第一级分含有39g的70%的5-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(IIIa-1)和30%的3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)的混合物。根据LC/MS,第二级分有10g,其由83%的3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(IIIb-1)组成。通过制备型HPLC将第一级分中的(IIIa-1)和(III-1)分离,又得到24.5g(纯度96%)5-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯作为甲酸酯(IIIa-1)和11.5g(纯度99%)3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)。
(IIIa-1).HCOOH logP[a]:1.18;logP[b]:1.27;1H NMR(D6-DMSO,400MHz)δppm:12.8(bs,1H),8.78(d,1H),8.62(dd,1H),8.14(s,1H),7.99-7.96(m,1H),7.76(s,1H),7.58(dd,1H),6.51(bs,2H),4.23(q,2H),1.28(t,3H)
(III-1)logP[a]:1.12;logP[b]:1.32;1H NMR(D6-DMSO,400MHz)δppm:9.06(d,1H),8.86(s,1H),8.47(d,1H),8.19(bd,1H),7.49(dd,1H),5.78(bs,2H),4.26(q,2H),1.30(t,3H)
通过方法C合成3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)
步骤1:苯甲醛吡啶-3-基腙(VII-1)
向于150ml甲苯中的15.00g(103.0mol)3-肼基吡啶盐酸盐(1:1)和9.49g(68.7mmol)碳酸钾中缓慢加入溶于100ml甲苯中的7ml(68.7mmol)苯甲醛。将反应混合物在回流下(带有水分离器)搅拌过夜。冷却后,抽吸滤出不溶的级分。将固体残余物在乙酸乙酯中反复搅拌。将固体物质抽吸滤出并在热的异丙醇中反复搅拌。将不溶的级分抽吸滤出并丢弃;将滤液浓缩。将得到的5.50g(纯度98%,理论值的40%)的标题化合物直接进行进一步转化。
logP[a]:0.86;logP[b]:2.22
步骤2:3-[2-亚苄基-1-(吡啶-3-基)肼基]-2-氰基丙烯酸乙酯(VIII-1)
向于14ml甲苯中的5.50g(27.9mmol)苯甲醛吡啶-3-基腙中加入4.72g(27.9mmol)2-氰基-3-乙氧基丙烯酸乙酯。将反应混合物先回流加热2h,加入一刮勺尖儿的对甲苯磺酸后,再回流加热2h。冷却后,抽吸滤出沉淀出的固体,并丢弃有机相。先将固体再次加入到15ml甲苯中,然后与1.69g(10.0mmol)2-氰基-3-乙氧基丙烯酸乙酯混合。将反应混合物回流加热过夜,然后静置直至冷却,随后用甲苯稀释。加入约0.5ml乙腈后,将不溶的残余物抽吸滤出并在真空下干燥。分离出3.11g(纯度90%,理论值的31%)的标题化合物。
logP[a]:2.54;logP[b]:2.48
步骤3:3-氨基-1-(吡啶-3-基)-1H-吡唑-4-甲酸乙酯(III-1)
首先将3.00g(9.37mmol)3-[2-亚苄基-1-(吡啶-3-基)肼基]-2-氰基丙烯酸乙酯加入到11ml乙醇中,然后加入1.1ml(13.11mmol)37%盐酸溶液。将反应混合物回流加热1h,冷却,然后浓缩。将残余物在微温的甲苯中搅拌两次。将固体物质抽吸滤出并在减压下干燥。分离出2.64g(纯度92%,理论值的97%)的标题化合物。
式(I)的其他化合物列于下表中。
表1
式(I-1)的化合物
其中V代表氧,R2代表氢,并且其余变量具有下表中所述的含义
表2
报告的所述化合物的分析数据
表3
式(I-2)的化合物
其中V代表氧,R2代表氢并且其余变量具有下表中所述的含义:
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,首先列出以ppm计的δ值,然后在圆括号中列出信号强度。不同信号峰的δ值-信号强度-峰对数通过分号彼此分隔列出。
因此,对于一个实施例,峰列表采取以下形式:
δ1(强度1);δ2(强度2);……..;δi(强度i);……;δn(强度n)
在打印出的NMR谱的实例中,尖峰信号的强度与以cm计的信号的高度相关,并且示出了信号强度的真实比例。在宽峰信号的情况下,可能示出了与谱图中最强的信号相比较的所述信号中的几个峰或中间峰及其相对强度。
对于1H NMR谱的化学位移的校正,我们使用四甲基硅烷和/或溶剂的化学位移,特别是在使用DMSO测得的谱图的情况下。因此,在NMR峰列表中,可出现但并不必须出现四甲基硅烷峰。
1H NMR峰的列表与常规1H NMR打印件相似,因此通常包含在常规NMR说明中列出的所有峰。
此外,与常规1H NMR打印件一样,它们可以示出溶剂信号、目标化合物的立体异构体(其同样形成本发明主题的一部分)的信号、和/或杂质的峰。
在报告溶剂和/或水中的化合物信号的δ范围时,我们的1H NMR峰的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,它们通常具有平均较高的强度。
目标化合物的立体异构体的峰和/或杂质的峰的平均强度通常比目标化合物(例如,纯度>90%)的峰的强度更低。
这类立体异构体和/或杂质是特定的制备方法特有的。因此,在这种情况下,它们的峰可有助于根据“副产物指纹(by-product fingerprint)”来识别我们的制备方法的再现性。
如果需要,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任选地使用其他强度滤波器来分离目标化合物的峰。这种分离与从常规1H NMR说明中选择相关峰相似。
1H NMR峰列表的其他细节可见于研究公开数据库(Research DisclosureDatabase)第564025号。
生物实施例
家蝇(Musca domestica)试验(MUSCDO)
溶剂:二甲基亚砜
为制备合适的活性成分制剂,将10mg活性成分与0.5ml二甲基亚砜混合,并将该浓缩液用水稀释至所需浓度。
将10只成年家蝇(Musca domestica)放入包含用糖溶液和所需浓度的活性成分制剂处理过的海绵的容器中。
2天后,测定以%计的杀死率。100%意指所有苍蝇已被杀死;0%意指没有苍蝇被杀死。
在该试验中,例如,制备实施例的以下化合物在100ppm的施用率下表现出80%的功效:I-1-2、I-1-3。
桃蚜(Myzuspersicae)-喷雾试验(MYZUPE)
溶剂:78重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充直到达到所需浓度。为制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的绿桃蚜(Myzus persicae)侵染的大白菜(Brassica pekinensis)叶盘上喷洒所需浓度的活性成分制剂。
6天后,测定以%计的功效。100%意指所有蚜虫已被杀死;0%意指没有蚜虫被杀死。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下表现出100%的功效:I-1-2、I-1-3、I-1-4、I-1-5、I-1-10、I-1-11。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下表现出90%的功效:I-1-6、I-1-7、I-1-8、I-1-12、I-1-14、I-1-15、I-1-16、I-1-17、I-1-18、I-1-19、I-1-21、I-1-22、I-2-23。
在该试验中,例如,来自制备实施例的以下化合物在100g/ha的施用率下表现出90%的功效:I-1-9。
在该试验中,例如,来自制备实施例的以下化合物在20g/ha的施用率下表现出90%的功效:I-1-20。
二斑叶螨(Tetranychus urticae)-喷雾试验,OP-抗性(TETRUR)
溶剂:78.0重量份的丙酮
1.5重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充直到达到所需浓度。为制备其他试验浓度,将该制剂用含有乳化剂的水稀释。
向被所有阶段的温室红叶螨(greenhouse red spider mite)(二斑叶螨(Tetranychus urticae))侵染的菜豆(Phaseolus vulgaris)叶盘上喷洒所需浓度的活性化合物制剂。
6天后,测定以%计的功效。100%意指所有叶螨已被杀死;0%意指没有叶螨被杀死。
在该试验中,例如,来自制备实施例的以下化合物在500g/ha的施用率下表现出100%的功效:I-1-4。
在该试验中,例如,来自制备实施例的以下化合物在500g/ha的施用率下表现出90%的功效:I-1-20。
桃蚜-喷雾试验(MYZUPE)
溶剂:7重量份的二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性成分制剂,将1重量份的活性成分用指定重量份的溶剂溶解,并用含有浓度为1000ppm的乳化剂的水补充直到达到所需浓度。为制备其他试验浓度,将该制剂用含有乳化剂的水稀释。如果需要添加铵盐或/和渗透剂,则将它们各自以1000ppm的浓度添加至制剂溶液。
通过喷洒所需浓度的活性成分制剂来处理被绿桃蚜(Myzus persicae)严重侵染的甜椒(Capsicum annuum)植株。
6天后,测定以%计的杀死率。100%意指所有蚜虫已被杀死;0%意指没有蚜虫被杀死。
在此试验中,例如,来自制备实施例的以下化合物在20ppm的施用率下表现出100%的功效:I-1-1。
在此试验中,例如,来自制备实施例的以下化合物在4ppm的施用率下表现出100%的功效:I-1-13。
Claims (11)
1.式(I)化合物
其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表C1-C6-烷基,其任选地被卤素取代;或代表C3-C6-环烷基-C1-C4-烷基,
W代表选自以下的基团:S和SO,
X代表选自以下的基团:氢、卤素和C1-C6-烷基,
Y代表选自以下的基团:氢、卤素和C1-C6-烷基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自以下的基团:氢和C1-C6-烷基,
V代表氧。
2.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表C1-C6-烷基,其任选地被卤素单取代至七取代;或代表C3-C6-环烷基-C1-C4-烷基,
W代表选自S和SO基团,
X代表选自以下的基团:氢、氟、氯、溴、碘和C1-C4-烷基,
Y代表选自以下的基团:氢、氟、氯、溴、碘和C1-C4-烷基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自以下的基团:氢和C1-C4-烷基,
V代表氧。
3.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表C1-C4-烷基,其任选地被氟、氯单取代、二取代、三取代、四取代或五取代;或代表C3-C6-环烷基-C1-C2-烷基,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
Y代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自以下的基团:氢和甲基,
V代表氧。
4.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表选自以下的基团:
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基,其中的每一个任选地被氟单取代、二取代或三取代;或代表C3-C6-环烷基甲基,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
Y代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自以下的基团:氢和甲基,
V代表氧。
5.根据权利要求1所述的式(I)的化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基,其中的每一个任选地被氟单取代、二取代或三取代;或代表C3-C6-环烷基甲基,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
Y代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
6.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基,其中的每一个任选地被氟单取代、二取代或三取代;或代表C3-C6-环烷基甲基,
W代表选自S和SO基团,
X代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
Y代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
7.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基,其中的每一个任选地被氟单取代、二取代或三取代;或代表C3-C6-环烷基甲基,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
Y代表选自以下的基团:氢、氟、氯、溴、甲基和乙基,
R2代表氢,
Q代表氮或C-R3,
R3代表选自氢和甲基的基团,
V代表氧。
8.根据权利要求1所述的式(I)化合物,其中
G代表C-A1,
A1代表氢,
T代表电子对或氧,
R1代表下式的基团
其中用星号(*)标记与式(I)的C(=V)-N-Q基团的氮原子连接的键,
R代表选自甲基、三氟乙基和环丙基甲基的基团,
W代表选自S和SO的基团,
X代表选自以下的基团:氢、氟、氯和甲基,
Y代表选自氢、氯和甲基的基团,
R2代表氢,
Q代表氮或C-R3,
R3代表氢或甲基,并且
V代表氧。
9.组合物,其特征在于含有至少一种根据权利要求1至8中任一项所述的式(I)化合物以及常规增量剂和/或表面活性物质。
10.根据权利要求1至8中任一项所述的式(I)化合物或根据权利要求9所述的组合物用于非治疗目的地防治害虫的用途。
11.式(II)的化合物
其中G、T、R1和R2具有权利要求1中所提及的含义。
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- 2015-03-06 US US15/124,122 patent/US9920059B2/en not_active Expired - Fee Related
- 2015-03-06 BR BR112016020756A patent/BR112016020756A2/pt not_active Application Discontinuation
- 2015-03-06 JP JP2016556854A patent/JP6445040B2/ja not_active Expired - Fee Related
- 2015-03-06 ES ES15707980.7T patent/ES2685970T3/es active Active
- 2015-03-06 EP EP15707980.7A patent/EP3116868B1/de not_active Not-in-force
- 2015-03-06 TW TW104107123A patent/TW201623308A/zh unknown
- 2015-03-06 CN CN201580022756.9A patent/CN106255686B/zh not_active Expired - Fee Related
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JP6445040B2 (ja) | 2018-12-26 |
CN106255686A (zh) | 2016-12-21 |
WO2015135843A1 (de) | 2015-09-17 |
TW201623308A (zh) | 2016-07-01 |
EP3116868A1 (de) | 2017-01-18 |
BR112016020756A2 (pt) | 2018-08-07 |
JP2017509626A (ja) | 2017-04-06 |
US20170226107A1 (en) | 2017-08-10 |
EP3116868B1 (de) | 2018-06-06 |
ES2685970T3 (es) | 2018-10-15 |
AR099701A1 (es) | 2016-08-10 |
US9920059B2 (en) | 2018-03-20 |
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