CN105324374B - 用于对抗动物害虫的n-取代酰基-亚氨基-吡啶化合物和衍生物 - Google Patents
用于对抗动物害虫的n-取代酰基-亚氨基-吡啶化合物和衍生物 Download PDFInfo
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- CN105324374B CN105324374B CN201480034839.5A CN201480034839A CN105324374B CN 105324374 B CN105324374 B CN 105324374B CN 201480034839 A CN201480034839 A CN 201480034839A CN 105324374 B CN105324374 B CN 105324374B
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- 229930003945 thebaine Natural products 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- GINSRDSEEGBTJO-UHFFFAOYSA-N thietane 1-oxide Chemical compound O=S1CCC1 GINSRDSEEGBTJO-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- PPEZWDDRWXDXOQ-UHFFFAOYSA-N tributoxy(sulfanylidene)-$l^{5}-phosphane Chemical class CCCCOP(=S)(OCCCC)OCCCC PPEZWDDRWXDXOQ-UHFFFAOYSA-N 0.000 description 1
- 229940116861 trichinella britovi Drugs 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- UGCNRZFAUBJVPT-UHFFFAOYSA-N tricyclohexyltin;hydrate Chemical compound O.C1CCCCC1[Sn](C1CCCCC1)C1CCCCC1 UGCNRZFAUBJVPT-UHFFFAOYSA-N 0.000 description 1
- MCVUKOYZUCWLQQ-UHFFFAOYSA-N tridecylbenzene Chemical compound CCCCCCCCCCCCCC1=CC=CC=C1 MCVUKOYZUCWLQQ-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 239000002753 trypsin inhibitor Substances 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
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000002578 wasp venom Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 210000002268 wool Anatomy 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
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 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
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/14—Ectoparasiticides, e.g. scabicides
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- 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
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
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Abstract
本发明涉及式(I)的N‑取代酰基‑亚氨基‑吡啶化合物、其对映体、非对映体和盐以及包含这类化合物的组合物。本发明还涉及这些N‑取代酰基‑亚氨基‑吡啶化合物和包含它的组合物对抗和防治动物害虫的方法和用途。此外,本发明还涉及施用该N‑取代酰基‑亚氨基‑吡啶化合物的农药方法。本发明N‑取代酰基‑亚氨基‑吡啶化合物由下式I定义,其中p、X、Y、W1、W2、W3、W4、Het、R1、R2、R3a、R3b、R4a、R4b和R5如说明书中所定义。
Description
本发明涉及N-取代酰基-亚氨基-吡啶化合物,其对映体、非对映体、衍生物和盐以及包含这类化合物的组合物。本发明还涉及N-取代酰基-亚氨基-吡啶化合物、其盐或者包含它们的组合物在对抗动物害虫中的用途。此外,本发明还涉及施用这类化合物的方法。
动物害虫破坏生长和收获的作物并且侵袭木制住宅和商业建筑,对食品供应和财产造成大的经济损失。尽管已知许多杀虫试剂,但由于目标害虫能够对所述试剂产生耐药性,仍然需要对抗动物害虫的新试剂。特别地,动物害虫如昆虫和螨难以被有效地防治。
因此,本发明的目的是提供具有良好的杀虫活性,尤其是对抗难以防治的昆虫和螨的化合物。
发现这些目的由用于防治和/或对抗动物害虫的通式I的N-取代酰基-亚氨基-吡啶衍生物和/或其对映体、非对映体、E/Z-异构体或者农业或兽用可接受盐解决:
其中:
p为选自0、1、2、3、4、5或6的整数;
X为O或S;
Y为O或S(O)m,其中m为0、1、2;
Het为5或6员碳结合或任选氮结合的杂环或杂芳环体系,各个环成员选自碳原子和至少1个至至多3个独立地选自硫、氧或氮的杂原子,其中碳、硫和氮环成员可独立地部分或完全氧化,且其中各个环任选被k个选自R6a的取代基取代,其中k为选自1、2、3、4或5的整数,且2个或更多个取代基R6a相互独立地选择;
W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成饱和、不饱和或部分不饱和5或6员含氮杂环,
其中W1、W2、W3和W4各自单独地表示CRw,其中各个:
Rw相互独立地选自氢、卤素、氰基、叠氮基、硝基、SCN、SF5、C1-C10烷基、C3-C8环烷基、C2-C10烯基、C2-C10炔基,且其中上述脂族和脂环族基团的碳原子可以为未被取代或者部分或完全卤代的,或者可任选进一步相互独立地被一个或多个R7取代;
OR8、NR9aR9b、S(O)nRa、S(O)nNR9aR9b、C(=O)R7、C(=O)NR9aR9b、C(=O)OR8、C(=S)R7、C(=S)NR9aR9b、C(=S)OR8、C(=S)SR8、C(=NR9a)R7、C(=NR9a)NR9aR9b、Si(R11)2R12;
苯基,其任选被1、2、3、4或5个独立地选自R10的取代基取代;3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2、3或4个选自氧、氮和/或硫的杂原子,任选被1、2、3、4或5个独立地选自R10的取代基取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
存在于一个环碳原子上的两个Rw可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a;
或者
相邻碳原子的两个Rw可一起并与现有键一起形成在相邻碳原子之间形成双键;
且其中:
W2或W3中的一个可任选表示相邻碳原子之间的单键或双键;
R1、R2相互独立地选自氢、卤素、CN、SCN、硝基、C1-C6烷基、C3-C6环烷基,其中上述脂族碳链基团各自为未被取代的、部分或完全卤代的或者可带有一个或多个基团R7的任意组合;
Si(R11)2R12、OR16、OSO2R16、S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)NR17aR17b、C(=S)NR17aR17b、C(=O)OR16、C(=O)R15、C(=S)R15,苯基,其任选被一个或多个,例如1、2、3、4或5个相互独立地选择的取代基R10取代,
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化,
或者
R1和R2与它们所连接的碳原子一起形成3-6员饱和或部分不饱和碳环或杂环,其中所述环的各个碳原子未被取代或者可带有1或2个基团R7的任意组合;
或者
R1和R2可一起为=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a;
R3a、R3b各自相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基和C3-C8环烷基,其中最后提到的6个基团各自为未被取代的、部分或完全卤代的,
OR8、OSO2R8、S(O)nR8、S(O)nNR9aR9b、NR9aR9b、C(=O)NR9aR9b、C(=S)NR9aR9b、C(=O)R7、C(=S)R7,
苯基,其任选被一个或多个,例如1、2、3、4或5个相互独立地选择的取代基R10取代,
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,其中杂环的氮和/或硫原子可任选被氧化,
或者
其中R3a和R3b可与它们所结合的碳原子一起形成3、4或5员脂族环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的,
或者
其中R3a和R3b可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a,并且,如果p为1或更大,
则R3a或R3b中的一个可与相邻碳原子的R4a或R4b形成双键,
R4a、R4b各自相互独立地且独立于整数p地选自氢、卤素、CN、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基和C3-C8环烷基,其中最后提到的6个基团各自为未被取代的、部分或完全卤代的,
或者
其中R4a和R4b可与它们所结合的碳原子一起形成3、4或5员脂族碳环,
其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的,
或者
其中R4a和R4b可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a,
或者如果p为1或更大,则R4a或R4b中的一个可与R3a或R3b或者与相邻碳原子的另一R4a或R4b形成双键,
R5选自氢、氰基、C1-C6烷基、C7-C12烷基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C3-C8环烷基、C3-C8环烷基硫基、C3-C8环烷基亚硫酰基、C3-C8环烷基磺酰基、C2-C6烯基、C2-C6烯硫基、C2-C6烯基亚硫酰基、C2-C6烯基磺酰基、C2-C6炔基、C2-C6炔硫基、C2-C6炔基亚硫酰基和C2-C6炔基磺酰基,其中上述脂族和脂环族基团的碳链原子为未被取代的、部分或完全卤代的或者可带有一个或多个基团R7的任意组合;
C(=O)NR9aR9b、C(=S)NR9aR9b、C(=O)R7、C(=S)R7;
苯基或CH2-苯基,其任选被一个或多个,例如1、2、3、4或5个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被q个独立于q且相互独立地选择的取代基Ry取代,且其中杂环的氮和/或硫原子可任选被氧化,其中杂环可直接结合在或者经由CH2基团连接在分子的其余部分上,且其中
q为选自1、2、3或4的整数,且
Ry选自氢、卤素、氰基、硝基、C1-C10烷基、C2-C10烯基,其中上述脂族基团的碳原子可任选被一个或多个相互独立地选择的R15取代,OR16、-S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)R15、C(=O)OR16、-C(=NR17a)R15、C(=O)NR17aR17b、C(=S)NR17aR17b,
或者
存在于部分饱和杂环的一个原子上的两个Ry一起可以为=O、=CR13R14;=NR17a、=NOR16或=NNR17a;
或者
相邻碳原子上的两个Ry可以为选自CH2CH2CH2CH2、CH=CH-CH=CH、N=CH-CH=CH、CH=N-CH=CH、N=CH-N=CH、CH2CH2CH2、CH=CHCH2、CH2CH2NR17a、CH2CH=N、CH=CH-NR17a的桥,并与两个Ry所结合的碳原子一起形成5员或6员稠合的部分饱和或不饱和、芳族碳环或杂环,其中环可任选被1个或2个选自=O、OH、CH3、OCH3、卤素、氰基、卤代甲基或卤代甲氧基的取代基取代;
R6a选自氢、卤素、氰基、叠氮基、硝基、SCN、SF5、C1-C10烷基、C3-C8环烷基、C2-C10烯基、C2-C10炔基,且其中上述脂族和脂环族基团的碳原子可任选进一步相互独立地被一个或多个R7取代,OR8、NR9aR9b、S(O)nR8、S(O)nNR9aR9b、C(=O)R7、C(=O)NR9aR9b、C(=O)OR8、C(=S)R7、C(=S)NR9aR9b、C(=S)OR8、C(=S)SR8、C(=NR9a)R7、C(=NR9a)NR9aR9b、Si(R11)2R12;
苯基,其任选被1、2、3、4或5个独立地选自R10的取代基取代;3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2、3或4个选自氧、氮和/或硫的杂原子,任选被1、2、3、4或5个独立地选自R10的取代基取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者存在于一个环碳或硫原子上的两个R6a可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a;
或者两个R6a一起形成C2-C7亚烷基链,因此与它们所结合的环原子一起形成3-、4-、5-、6-、7-或8员环,其中亚烷基链可被1或2个O、S和/或NR17a间隔和/或亚烷基链的1或2个CH2基团可被基团C=O、C=S和/或C=NR17a替代;和/或亚烷基链可被一个或多个选自如下的基团取代:卤素、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基,可被1个或多个,例如1、2、3、4或5个基团R10取代的苯基,和包含1、2或3个选自N、O、S、NO、SO和SO2的杂原子或杂原子基团作为环成员的3-、4-、5-、6-或7员饱和、部分不饱和或芳族杂环,其中杂环可被一个或多个基团R10取代;
R7各自相互独立地选自氢、卤素、氰基、叠氮基、硝基、-SCN、SF5、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、Si(R11)2R12、OR16、OSO2R16、S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)NR17aR17b、C(=S)NR17aR17b、C(=O)OR16、C(=O)R15、C(=S)R15、C(=NR17a)R15,
苯基,其任选被1、2、3、4或5个相互独立地选择的取代基R10取代,3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化,
或者
存在于一个碳原子上的两个R7可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a;
或者
两个R7可与这两个R7所结合的碳原子一起形成3-、4-、5-、6-、7-或8员饱和或部分不饱和碳环或杂环;
R8各自相互独立地选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C3-C8环烷基、C4-C8烷基环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、-Si(R11)2R12、S(O)nR16、S(O)nNR17aR17b、NR17aR17b、-N=CR13R14、-C(=O)R15、C(=O)NR17aR17b、C(=S)NR17aR17b、C(=O)OR16,
苯基,其任选被一个或多个相互独立地选择的取代基R10取代,3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
R9a、R9b各自相互独立地选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基,
S(O)nR16、-S(O)nNR17aR17b、C(=O)R15、C(=O)OR16、C(=O)NR17aR17b、C(=S)R15、C(=S)SR16、C(=S)NR17aR17b、C(=NR17a)R15;
苯基,其任选被一个或多个,例如1、2、3或4个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2、3或4个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
R9a和R9b一起为C2-C7亚烷基链并与它们所结合的氮原子一起形成3-、4-、5-、6-、7-或8员饱和、部分饱和或不饱和芳环,其中亚烷基链可包含1或2个选自氧、硫或氮的杂原子并且可任选被卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基取代,
苯基,其任选被一个或多个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被一个或多个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
R9a和R9b可一起形成=CR13R14、=NR17或=NOR16基团;
R10各自相互独立地选自氢、卤素、氰基、叠氮基、硝基、SCN、SF5、C1-C10烷基、C3-C8环烷基、C2-C10烯基、C2-C10炔基,其中上述脂族和脂环族基团的碳原子可任选被一个或多个相互独立地选择的R15取代,
Si(R11)2R12、OR16、OS(O)nR16、-S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)R15、C(=S)R15、C(=O)OR16、-C(=NR17a)R15、C(=O)NR17aR17b、C(=S)NR17aR17b,
苯基,其任选被卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代,
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被一个或多个独立地选自卤素、氰基、NO2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基的取代基取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
一起存在于部分饱和杂环的一个原子上的两个R10可以为=O、=CR13R14;=NR17a、=NOR16或=NNR17a;
或者
相邻碳原子上的两个R10可以为选自CH2CH2CH2CH2、CH=CH-CH=CH、N=CH-CH=CH、CH=N-CH=CH、N=CH-N=CH、OCH2CH2CH2、OCH=CHCH2、CH2OCH2CH2、OCH2CH2O、OCH2OCH2、CH2CH2CH2、CH=CHCH2、CH2CH2O、CH=CHO、CH2OCH2、CH2C(=O)O、C(=O)OCH2、O(CH2)O、SCH2CH2CH2、SCH=CHCH2、CH2SCH2CH2、SCH2CH2S、SCH2SCH2、CH2CH2S、CH=CHS、CH2SCH2、CH2C(=S)S、C(=S)SCH2、S(CH2)S、CH2CH2NR17a、CH2CH=N、CH=CH-NR17a、OCH=N、SCH=N的桥,并与两个R10所结合的碳原子一起形成5员或6员部分饱和或不饱和、芳族碳环或杂环,其中环可任选被1或2个选自=O、OH、CH3、OCH3、卤素、氰基、卤代甲基或卤代甲氧基的取代基取代;
R11、R12各自相互独立地选自氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6烷氧基烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷氧基烷基、C1-C6卤代烷氧基烷基,和苯基,其任选被一个或多个相互独立地选择的取代基R10取代;
R13、R14各自相互独立地选自氢、C1-C4烷基、C1-C6环烷基、C1-C4烷氧基烷基、苯基和苄基;
R15各自相互独立地选自氢、卤素、氰基、硝基、OH、SH、SCN、SF5、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,
C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个脂族和脂环族基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团;
苯基、苄基、吡啶基、苯氧基,其中后4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、(C1-C6烷氧基)羰基、(C1-C6烷基)氨基或二-(C1-C6烷基)氨基的取代基,
或者
存在于相同碳原子上的两个R15可一起为=O、=CH(C1-C4)、=C(C1-C4烷基)C1-C4烷基、=N(C1-C6烷基)或=NO(C1-C6烷基);
R16各自相互独立地选自氢、氰基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团,
苯基、苄基、吡啶基、苯氧基,其中后4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或(C1-C6烷氧基)羰基的取代基;
R17a、R17b各自相互独立地选自氢、氰基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,
C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个脂族和脂环族基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团,
苯基、苄基、吡啶基、苯氧基,其中后4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或(C1-C6烷氧基)羰基的取代基,
或者
R17a和R17b可一起为C2-C6亚烷基链,与R17a和R17b所结合的氮原子一起形成3-7员饱和、部分饱和或不饱和环,其中亚烷基链可含有1或2个选自氧、硫或氮的杂原子,并可任选被卤素、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代,且其中杂环的氮和/或硫原子可任选被氧化;
n为相互独立地选自0、1或2的整数。
取代的硝基亚氨基-和氰基亚氨基-吡啶及其作为农药的用途已公开于EP 259738中。类似的取代亚氨基吡啶作为除草剂已描述于EP 432600中。
三氟乙酰杂环基亚胺作为杀虫剂公开于EP 268915中。
取代的酰亚氨基吡啶作为杀虫剂已公开于WO 2012/029672中。其制备描述于WO2013/031671中。WO2013/129692涉及具有2-亚氨基的含氮杂环衍生物和使用它的新的害虫防治剂。某些杂环基亚胺及其作为杀虫剂的用途描述于WO 9215564中。
式I的N-取代酰基-亚氨基-吡啶化合物及其农业或兽用可接受盐对动物害虫,即有害节肢动物和线虫,尤其是对难以防治的昆虫和螨具有高活性。
因此,本发明涉及通式I的N-取代酰基-亚氨基-吡啶化合物,其农业或兽用有用盐、其对映体或非对映体。
此外,本发明涉及并包括以下实施方案:
-包含一定量的至少一种式I化合物或其对映体、非对映体或盐的农业和兽用组合物;
-式I化合物或其对映体、非对映体或盐在对抗动物害虫中的用途;
-对抗动物害虫的方法,其包括使动物害虫,其栖息地,繁殖地,食物源,动物害虫生长或可能生长的植物、种子、土壤、区域、材料或环境或者待保护以防动物侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种式I化合物或其对映体、非对映体或盐接触;
-保护作物以防动物害虫侵袭或侵染的方法,其包括使作物与杀虫有效量的至少一种式I化合物或其对映体、非对映体或盐接触;
-保护植物繁殖体,尤其是种子以防土壤昆虫以及保护秧苗的根和芽以防土壤和叶面昆虫的方法,其包括使种子在播种以前和/或催芽以后与至少一种式I化合物或其对映体、非对映体或盐接触;
-包含式I化合物或其对映体、非对映体或盐的种子;
-式I化合物或其对映体、非对映体或兽用可接受盐在对抗动物中和动物上的寄生虫的用途;
-处理、防治、防止或保护动物以防寄生虫侵袭或侵染的方法,其包括为动物口服、局部或肠道外给药或施用杀寄生虫有效量的式I化合物或其对映体、非对映体或兽用可接受盐;
-制备用于处理、防治、防止或保护动物以防寄生虫侵袭或侵染的兽用组合物的方法,其包括将杀寄生虫有效量的式I化合物或其对映体、非对映体或兽用可接受盐加入适于兽用用途的载体组合物中;
-式I化合物或其对映体、非对映体或兽用可接受盐在制备用于处理、防治、防止和/或保护动物以防寄生虫侵袭或侵染的药物中的用途。
本发明尤其涉及包含至少一种式I化合物和/或其农业可接受盐的植物繁殖材料,特别是如上所述种子。
本发明涉及式I化合物的每种可能的立体异构体,即单一对映体或非对映体以及其混合物。
本发明涉及各个单独的异构体或者异构体的彼此任意比例的混合物或组合。
本发明化合物可以为无定形的或者可以以一种或多种不同的晶态(多晶型)或晶型存在,这些晶态或晶型可具有不同的宏观性能如稳定性或显示出不同的生物性能如活性。本发明包括无定形和结晶的式I化合物、各化合物I的不同晶态或者晶型的混合物,以及式I化合物的无定形或结晶盐。
式I化合物的盐优选为农业和/或兽用可接受盐。它们可以以常规方法形成,例如如果式I化合物具有碱性官能的话通过使该化合物与涉及的阴离子的酸反应,或者通过使酸性式I化合物与合适的碱反应。
合适的农业或兽用有用盐尤其是那些阳离子的盐或那些酸的酸加成盐,所述盐的阳离子和阴离子分别对本发明化合物的作用不具有不利影响。合适的阳离子特别是碱金属,优选锂、钠和钾,碱土金属,优选钙、镁和钡,过渡金属,优选锰、铜、锌和铁的离子,以及铵(NH4 +)和其中1-4个氢原子被C1-C4烷基、C1-C4羟烷基、C1-C4烷氧基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的取代铵。取代铵离子的实例包括甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、四甲基铵、四乙基铵、四丁基铵、2-羟乙基铵、2-(2-羟基乙氧基)乙基铵、双(2-羟乙基)铵、苄基三甲基铵和苄基三乙基铵,还有离子、锍离子、优选三(C1-C4烷基)锍,和氧化锍离子,优选三(C1-C4烷基)氧化锍。
有用酸加成盐的阴离子主要是氯、溴、氟、硫酸氢根、硫酸根、磷酸二氢根、磷酸氢根、磷酸根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根,和C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。它们可通过使式I化合物与相应阴离子的酸,优选盐酸、氢溴酸、硫酸、磷酸或硝酸反应而形成。
变量的以上定义中提到的有机结构部分如同术语卤素一样为各基团成员的各个列举的集合性术语。前缀Cn-Cm每种情况下表示基团中可能的碳原子数目。
“卤素”意指氟、氯、溴和碘。
术语“部分或完全卤代”意指给定基团的1个或更多,例如1、2、3、4或5个或者所有氢原子被卤原子,特别是被氟或氯替代。
如本文所用术语“Cn-Cm烷基”(以及Cn-Cm烷基氨基、二-Cn-Cm烷基氨基、Cn-Cm烷基氨基羰基、二-(Cn-Cm烷基氨基)羰基、Cn-Cm烷硫基、Cn-Cm烷基亚硫酰基和Cn-Cm烷基磺酰基中的该术语)指具有n至m个,例如1-10个碳原子,优选1-6个碳原子的支化或非支化饱和烃基团,例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、庚基、辛基、2-乙基己基、壬基和癸基以及它们的异构体。C1-C4烷基意指例如甲基、乙基、丙基、1-甲基乙基、丁基、1-甲基丙基、2-甲基丙基或1,1-二甲基乙基。
如本文所用术语“Cn-Cm卤代烷基”(以及Cn-Cm卤代烷基亚硫酰基和Cn-Cm卤代烷基磺酰基中的该术语)指具有n至m个碳原子,例如1-10,特别是1-6个碳原子的直链或支化烷基(如上文所提到的),其中这些基团中的一些或所有氢原子可被如上所述卤原子替代,例如C1-C4卤代烷基,例如氯甲基、溴甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基、氯氟甲基、二氯氟甲基、氯二氟甲基、1-氯乙基、1-溴乙基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2-氯-2-氟乙基、2-氯-2,2-二氟乙基、2,2-二氯-2-氟乙基、2,2,2-三氯乙基、五氟乙基等。术语C1-C10卤代烷基特别包括C1-C2氟烷基,其与其中1、2、3、4或5个氢原子被氟原子替代的甲基或乙基是同义词,例如氟甲基、二氟甲基、三氟甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基和五氟甲基。
类似地,“Cn-Cm烷氧基”和“Cn-Cm烷硫基”(或者Cn-Cm烷基硫基分别)指在烷基的任何键位置分别通过氧或硫连接键键合的具有n至m个碳原子,例如1-10,特别是1-6或1-4个碳原子的直链或支化烷基(如上文所提到的)。实例包括C1-C4烷氧基,例如甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、仲丁氧基、异丁氧基和叔丁氧基,还有C1-C4烷硫基,例如甲硫基、乙硫基、丙硫基、异丙硫基和正丁硫基。
因此,术语“Cn-Cm卤代烷氧基”和“Cn-Cm卤代烷硫基”(或者Cn-Cm卤代烷基硫基分别)指在烷基的任何键位置分别通过氧或硫连接键键合的具有n至m个碳原子,例如1-10,特别是1-6或1-4个碳原子的直链或支化烷基(如上文所提到的),其中这些基团中的一些或所有氢原子可被如上所述卤原子替代,例如C1-C2卤代烷氧基,例如氯甲氧基、溴甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、二氯氟甲氧基、氯二氟甲氧基、1-氯乙氧基、1-溴乙氧基、1-氟乙氧基、2-氟乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、2-氯-2-氟乙氧基、2-氯-2,2-二氟乙氧基、2,2-二氯-2-氟乙氧基、2,2,2-三氯乙氧基和五氟乙氧基,还有C1-C2卤代烷硫基,例如氯甲硫基、溴甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基、二氯氟甲硫基、氯二氟甲硫基、1-氯乙硫基、1-溴乙硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、2,2,2-三氟乙硫基、2-氯-2-氟乙硫基、2-氯-2,2-二氟乙硫基、2,2-二氯-2-氟乙硫基、2,2,2-三氯乙硫基和五氟乙硫基等。类似地,术语C1-C2氟烷氧基和C1-C2氟烷硫基指分别经由氧原子或硫原子与分子的其余部分键合的C1-C2氟烷基。
如本文所用术语“C2-Cm烯基″”意指具有2至m,例如2-10或2-6个碳原子和在任何位置上的双键的支化或非支化不饱和烃基团,例如乙烯基、1-丙烯基、2-丙烯基、1-甲基-乙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基、2-甲基-1-丙烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、1-戊烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-1-丁烯基、2-甲基-1-丁烯基、3-甲基-1-丁烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-1-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-1-丙烯基、1-乙基-2-丙烯基、1-己烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-1-戊烯基、2-甲基-1-戊烯基、3-甲基-1-戊烯基、4-甲基-1-戊烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、1-甲基-3-戊烯基、2-甲基-3-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-1-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-1-丁烯基、1,3-二甲基-2-丁烯基、1,3-二甲基-3-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-1-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、3,3-二甲基-1-丁烯基、3,3-二甲基-2-丁烯基、1-乙基-1-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-1-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基、1-乙基-2-甲基-1-丙烯基和1-乙基-2-甲基-2-丙烯基。
如本文所用术语“C2-Cm炔基”指具有2至m,例如2-10或2-6个碳原子且包含至少一个三键的支化或非支化不饱和烃基团,例如乙炔基、丙炔基、1-丁炔基、2-丁炔基等。
如本文所用术语“C1-C4烷氧基-C1-C4烷基”指具有1-4个碳原子的烷基,例如如上文提到的具体实例,其中烷基的一个氢原子被C1-C4烷氧基替代。
如本文所用术语“C3-Cm环烷基”指单环3至m员饱和脂环族基团,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基和环癸基。
如本文所用术语“芳基”指芳族烃基,例如萘基或者特别是苯基。
如本文所用术语“3-6员碳环”指环丙烷、环丁烷、环戊烷和环己烷环。
如本文所用术语“包含1、2或3个杂原子的3-、4-、5-、6-或7员饱和、部分不饱和或芳族杂环”或者“包含杂原子”,其中那些杂原子(基团)选自N、O、S、NO、SO和SO2且为环成员,指单环基团,其中单环基团为饱和、部分不饱和或芳族的。杂环基团可经由碳环成员或者经由氮环成员连接在分子的其余部分上。
3-、4-、5-、6-或7员饱和杂环基或杂环的实例包括:氧杂环丙烷基、氮杂环丙烷基、氮杂环丁烷基、2-四氢呋喃基、3-四氢呋喃基、2-四氢噻吩基、3-四氢噻吩基、2-吡咯烷基、3-吡咯烷基、3-吡唑烷基、4-吡唑烷基、5-吡唑烷基、2-咪唑烷基、4-咪唑烷基、2-唑烷基、4-唑烷基、5-唑烷基、3-异唑烷基、4-异唑烷基、5-异唑烷基、2-噻唑烷基、4-噻唑烷基、5-噻唑烷基、3-异噻唑烷基、4-异噻唑烷基、5-异噻唑烷基、1,2,4-二唑烷-3-基、1,2,4-二唑烷-5-基、1,2,4-噻二唑烷-3-基、1,2,4-噻二唑烷-5-基、1,2,4-三唑烷-3-基、1,3,4-二唑烷-2-基、1,3,4-噻二唑烷-2-基、1,3,4-三唑烷-2-基、2-四氢吡喃基、4-四氢吡喃基、1,3-二烷-5-基、1,4-二烷-2-基、2-哌啶基、3-哌啶基、4-哌啶基、3-六氢哒嗪基、4-六氢哒嗪基、2-六氢嘧啶基、4-六氢嘧啶基、5-六氢嘧啶基、2-哌嗪基、1,3,5-六氢三嗪-2-基和1,2,4-六氢三嗪-3-基、2-吗啉基、3-吗啉基、2-硫代吗啉基、3-硫代吗啉基、1-氧硫代吗啉-2-基、1-氧硫代吗啉-3-基、1,1-二氧硫代吗啉-2-基、1,1-二氧硫代吗啉-3-基、六氢氮杂环庚烯-1-、-2-、-3-或-4-基、六氢氧杂环庚烯基、六氢-1,3-二氮杂环庚烯基、六氢-1,4-二氮杂环庚烯基、六氢-1,3-氧氮杂环庚烯基、六氢-1,4-氧氮杂环庚烯基、六氢-1,3-二氧杂环庚烯基、六氢-1,4-二氧杂环庚烯基等。
3-、4-、5-、6-或7员部分不饱和杂环基或杂环的实例包括:2,3-二氢呋喃-2-基、2,3-二氢呋喃-3-基、2,4-二氢呋喃-2-基、2,4-二氢呋喃-3-基、2,3-二氢噻吩-2-基、2,3二氢噻吩-3-基、2,4二氢噻吩-2-基、2,4-二氢噻吩-3-基、2-吡咯啉-2-基、2-吡咯啉-3-基、3吡咯啉-2-基、3-吡咯啉-3-基、2-异唑啉-3-基、3-异唑啉-3-基、4异唑啉-3-基、2-异唑啉-4-基、3-异唑啉-4-基、4-异唑啉-4-基、2异唑啉-5-基、3-异唑啉-5-基、4-异唑啉-5-基、2-异噻唑啉-3-基、3异噻唑啉-3-基、4-异噻唑啉-3-基、2-异噻唑啉-4-基、3-异噻唑啉-4-基、4异噻唑啉-4-基、2-异噻唑啉-5-基、3-异噻唑啉-5-基、4-异噻唑啉-5-基、2,3-二氢吡唑-1-基、2,3-二氢吡唑-2-基、2,3-二氢吡唑-3-基、2,3-二氢吡唑-4-基、2,3-二氢吡唑-5-基、3,4-二氢吡唑-1-基、3,4-二氢吡唑-3-基、3,4-二氢吡唑-4-基、3,4-二氢吡唑-5-基、4,5-二氢吡唑-1-基、4,5-二氢吡唑-3-基、4,5-二氢吡唑-4-基、4,5-二氢吡唑-5-基、2,3-二氢唑-2-基、2,3-二氢唑-3-基、2,3-二氢唑-4-基、2,3-二氢唑-5-基、3,4-二氢唑-2-基、3,4-二氢唑-3-基、3,4-二氢唑-4-基、3,4-二氢唑-5-基、3,4-二氢唑-2-基、3,4-二氢唑-3-基、3,4-二氢唑-4-基、2-、3-、4-、5-或6-二-或四氢吡啶基、3-二-或四氢哒嗪基、4-二-或四氢哒嗪基、2-二-或四氢嘧啶基、4-二-或四氢嘧啶基、5-二-或四氢嘧啶基、二-或四氢吡嗪基、1,3,5-二-或四氢三嗪-2-基、1,2,4-二-或四氢三嗪-3-基、2,3,4,5-四氢[1H]氮杂环庚烯-1-、-2-、-3-、-4-、-5-、-6-或-7-基、3,4,5,6-四氢[2H]氮杂环庚烯-2-、-3-、-4-、-5-、-6-或-7-基、2,3,4,7四氢[1H]氮杂环庚烯-1-、-2-、-3-、-4-、-5-、-6-或-7-基、2,3,6,7四氢[1H]氮杂环庚烯-1-、-2-、-3-、-4-、-5-、-6-或-7-基、四氢氧杂环庚烯基,例如2,3,4,5-四氢[1H]氧杂环庚烯-2-、-3-、-4-、-5-、-6-或-7-基、2,3,4,7四氢[1H]氧杂环庚烯-2-、-3-、-4-、-5-、-6-或-7-基、2,3,6,7四氢[1H]氧杂环庚烯-2-、-3-、-4-、-5-、-6-或-7-基、四氢-1,3-二氮杂环庚烯基、四氢-1,4-二氮杂环庚烯基、四氢-1,3-氧氮杂环庚烯基、四氢-1,4-氧氮杂环庚烯基、四氢-1,3-二氧杂环庚烯基和四氢-1,4-二氧杂环庚烯基。
5-或6员芳族杂环基(杂芳基)或杂芳环的实例为:2-呋喃基、3-呋喃基、2-噻吩基、3-噻吩基、2-吡咯基、3-吡咯基、3-吡唑基、4-吡唑基、5-吡唑基、2-唑基、4-唑基、5-唑基、2-噻唑基、4 噻唑基、5-噻唑基、2-咪唑基、4-咪唑基、1,3,4-三唑-2-基、2-吡啶基、3-吡啶基、4-吡啶基、3-哒嗪基、4-哒嗪基、2-嘧啶基、4-嘧啶基、5-嘧啶基和2-吡嗪基。
“C2-Cm亚烷基”为具有2至m,例如2-7个碳原子的二价支化或者优选非支化饱和脂族链,例如CH2CH2、-CH(CH3)-、CH2CH2CH2、CH(CH3)CH2、CH2CH(CH3)、CH2CH2CH2CH2、CH2CH2CH2CH2CH2、CH2CH2CH2CH2CH2CH2和CH2CH2CH2CH2CH2CH2CH2。
优选
本发明的实施方案和优选化合物描述于以下段落中。
下文关于式I化合物的变量,尤其是关于其取代基X、Y、W1、W2、W3、W4、Het、R1、R2、R3a、R3b、R4a、R4b和R5及其变量p的优选实施方案做出的注释对于它们本身以及特别是彼此的每种可能的组合都是有效的。
当#在显示本发明化合物的优选结构的式中出现时,它表示在其余分子中的连接键。
优选的是其中Het选自式Het-1至Het-28的基团的式(I)化合物:
其中#表示式(I)中的键,k为0、1或2,且R6a具有如下文进一步定义的优选含义。
尤其优选这样的式(I)化合物,其中Het选自式Het-1、Het-11a和Het-24的基团:
且其中#表示式(I)中的键,k为0、1或2,且R6a具有如下文进一步定义的优选含义。
尤其更优选这样的式(I)化合物,其中Het为Het-1a:
且其中#表示式(I)中的键,且R6a具有如下文进一步定义的优选含义。
尤其更优选这样的式(I)化合物,其中Het为Het-11a:
且其中#表示式(I)中的键,且R6a具有如下文进一步定义的优选含义。
尤其优选这样的式(I)化合物,其中Het为Het-24:
且其中#表示式(I)中的键,且其中k为0。
尤其优选这样的式(I)化合物,其中Het为Het-24,且其中#表示式(I)中的键,且其中k选自1或2,且R6a具有如下文进一步定义的优选含义。
尤其更优选这样的式(I)化合物,其中Het为Het-23a:
且其中#表示式(I)中的键,且R6a具有如下文进一步定义的优选含义。
优选这样的式(I)化合物,其中在Het上,k选自0、1或2。
尤其优选这样的式(I)化合物,其中在Het上,k为0、1或2且R6a具有如下文中所定义的优选含义。
优选这样的式(I)化合物,其中Het被R6a取代,所述R6a各自相互独立地选自氢、卤素、氰基、C1-C6烷基、C3-C8环烷基、C2-C6烯基、C2-C6炔基,其中上述脂族和脂环族基团的碳原子可任选进一步相互独立地被一个或多个R7取代,OR8、NR9aR9b、S(O)nR8、S(O)nNR9aR9b、C(=O)R7、C(=O)NR9aR9b、C(=O)OR8、C(=S)R7、C(=S)NR9aR9b、C(=NR9a)R7、C(=NR9a)NR9aR9b。
尤其优选这样的式(I)化合物,其中Het被R6a取代,所述R6a各自相互独立地选自氢、卤素、C1-C4烷氧基或C1-C4烷基,其中后两个基团的碳原子可以为部分或完全卤代的。
优选这样的式(I)化合物,其中R1和R2相互独立地选自氢、卤素、CN、C1-C6烷基、C3-C6环烷基、C1-C6卤代烷基、C2-C6卤代环烷基;或者
R1和R2可以一起为=O、=CR13R14或=S;或者
R1和R2与它们所连接的碳原子一起形成3-5员饱和碳环。
尤其优选这样的式(I)化合物,其中R1和R2相互独立地选自氢、卤素、氰基、C1-C3烷基或C1-C3卤代烷基。
尤其优选这样的式(I)化合物,其中R1和R2都为氢。
尤其优选这样的式(I)化合物,其中R1为氢,且R2为CH3。
优选这样的式(I)化合物,其中R3a和R3b各自相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基和OR8,其中R8为C(=O)R15,且R15为C1-C6烷基,其中脂族基团可以为未被取代的、部分或完全卤代的。
优选这样的式(I)化合物,其中R3a、R3b各自相互独立地选自氢、卤素、CN、C1-C6烷基和C1-C6卤代烷基。
尤其优选这样的式(I)化合物,其中R3a、R3b各自相互独立地选自氢或氟。
优选这样的式(I)化合物,其中R3a、R3b与它们所结合的碳原子一起形成环丙烷环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的。
优选这样的式(I)化合物,其中p为0。
优选这样的式(I)化合物,其中p为1,且R4a、R4b相互独立地选自氢或卤素。
尤其优选这样的式(I)化合物,其中p为1,且R4a、R4b相互独立地选自氢或氟。
尤其优选这样的式(I)化合物,其中p为1,且其中R4a和R4b中的一个可与相邻碳原子的R3a或R3b形成双键。
优选这样的式(I)化合物,其中X为S。
优选这样的式(I)化合物,其中X为O。
优选这样的式(I)化合物,其中Y选自O。
优选这样的式(I)化合物,其中Y选自S、S=O或S(O)2。
尤其优选这样的式(I)化合物,其中Y选自S。
尤其优选这样的式(I)化合物,其中Y选自S=O。
尤其优选式(I)化合物,其中Y选自S(O)2。
优选这样的式(I)化合物,其中R5选自氢、氰基、C1-C6烷基、C7-C10烷基、C3-C10环烷基、C2-C6烯基和C2-C6炔基,其中上述4个脂族和脂环族基团的碳链原子为未被取代的、部分或完全卤代的或者可带有一个或多个基团R7的任意组合,其中R7相互独立地选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或C(=O)O-R16,且其中R16相互独立地为C1-C6烷基,其中烷基可以为未被取代的、部分或完全卤代的和/或可带有1或2个选自C1-C4烷氧基的基团。
优选这样的式(I)化合物,其中R5选自苯基或CH2-苯基,其任选被1、2或3个取代基取代,所述取代基相互独立地选自氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或苯氧基。
优选这样的式(I)化合物,其中R5选自5-或6-员饱和、部分饱和或不饱和芳族杂环,所述芳族杂环选自吡啶、呋喃、唑、二唑、异唑、噻唑、噻二唑或异噻唑,其中杂环可直接结合在或经由CH2基团连接在分子的其余部分上,其中杂环为未被取代或者任选被1、2或3个相互独立地选择的取代基Ry取代,且其中Ry选自卤素、氰基和C1-C4烷基,其中烷基的碳原子可以为未被取代或者部分或完全卤代的和/或可带有1、2或3个选自C1-C4烷氧基的基团。
优选这样的式(I)化合物,其中R5选自5-或6-员饱和、部分饱和或不饱和芳族杂环,所述芳族杂环选自吡啶、呋喃、唑、二唑、异唑、噻唑、噻二唑或异噻唑,其中杂环为未被取代或者任选被1、2或3个相互独立地选择的取代基Ry取代,且其中Ry选自卤素、氰基和C1-C4烷基,其中烷基的碳原子可以为未被取代或者部分或完全卤代的和/或可带有1、2或3个选自C1-C4烷氧基的基团。
优选这样的式(I)化合物,其中R5选自氢、卤素、氰基、C1-C6烷基、C3-C10环烷基、C2-C6烯基或C2-C6炔基,其中最后提到的4个脂族基团各自为未被取代的、部分或完全卤代的。
优选这样的式(I)化合物,其中R5选自S-CN、C1-C4烷硫基、C3-C6环烷基硫基、C2-C6烯硫基和C2-C6炔硫基,其中最后提到的4个脂族基团各自为未被取代的、部分或完全卤代的。
优选这样的式(I)化合物,其中R5为苯基或苄基。
优选这样的式(I)化合物,其中R5为苯基或CH2-苯基,其中芳环任选被1或2个取代基取代,所述取代基相互独立地选自氢、卤素、CN、C1-C4烷基、C1-C4烷氧基,其中最后提到的2个脂族基团都可以为未被取代或者部分或完全卤代的。
优选这样的式(I)化合物,其中R5为选自如下的5-或6-员芳族杂环:
其中#表示与分子其余部分的键,且
其中该键可以为单键或者经由CH2基团连接在分子的其余部分上;
其中:
q选自0、1或2,且其中:
Ry独立于q值且相互独立地选自氢、卤素、CN、-C1-C4烷基和C1-C4烷氧基,其中最后提到的2个脂族基团都可以为未被取代的、部分或完全卤代的,
苯基,其任选被卤素、氰基、硝基、C1-C4烷基和C1-C4烷氧基取代,其中最后提到的2个脂族基团都可以为未被取代的、部分或完全卤代的,
或者
相邻碳原子上的两个Ry可以为选自CH=CH-CH=CH或CH=CHCH2的桥,并因此与这两个Ry所结合的碳原子一起形成稠合的5员或6员芳族碳环,其中该环可任选被一个或多个取代基取代,所述取代基选自卤素、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷基或C1-C4卤代烷基。
优选这样的式(I)化合物,其中W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成饱和、不饱和或部分不饱和6员含氮杂环,所述含氮杂环选自W.Het-1、W.Het-2、W.Het-3、W.Het-4、W.Het-5、W.Het-6、W.Het-7、W.Het-8、W.Het-9、W.Het-10、W.Het-11和W.Het-12:
其中#表示与分子其余部分的键;R1、R2和Het如上文所定义,且其中Rw3、Rw4、Rw5和Rw6选自氢、卤素、C1-C4烷氧基和C1-C4烷基,其中最后提到的两个脂族基团都可以为未被取代的、部分或完全卤代的。
尤其优选这样的式(I)化合物,其中W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成选自W.Het-1、W.Het-5和W.Het-9的饱和、不饱和或部分不饱和6员含氮杂环:
其中#表示与分子其余部分的键,且Rw6选自氢、卤素、C1-C4烷基;或C1-C4卤代烷基。
优选这样的式(I)化合物,其中各个Rw相互独立地选自氢、卤素、C1-C4烷氧基或C1-C4烷基,其中最后提到的两个脂族基团都可以为未被取代的、部分或完全卤代的。
优选的本发明化合物为这样的式(I)化合物:
其中:
W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成选自W.Het-1、W.Het-5和W.Het-9的饱和、不饱和或部分不饱和6员含氮杂环:
其中#表示与分子其余部分的键,且其中Rw6选自氢、卤素、C1-C4烷基;或C1-C4卤代烷基;且其中:
Het选自式Het-1、Het-11a和Het-24的基团:
其中#表示式(I)中的键,且其中R6a选自氢、卤素、C1-C4烷氧基或C1-C4烷基,其中后两个基团的碳原子可以为部分或完全卤代的;
k为0、1或2;
且其中进一步:
R1、R2相互独立地选自氢、卤素、氰基、C1-C3烷基或C1-C3卤代烷基;
X选自O或S;
R3a、R3b相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6卤代烷基,或者其中R3a、R3b与它们所结合的碳原子一起形成环丙烷环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的;
p为0;
Y为S(O)m,其中m为0、1或2;
且
R5选自氢、卤素、CN、S-CN、C1-C6烷基、C1-C4烷硫基、C3-C6环烷基、C3-C6环烷基硫基、C2-C6烯基、C2-C6烯硫基、C2-C6炔基或C2-C6炔硫基,其中最后提到的8个脂族和脂环族基团各自为未被取代的、部分或完全卤代的。
尤其优选这样的式(I)化合物,其中:
W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成不饱和6员含氮杂环W.Het-1:
其中#表示与分子其余部分的键,且其中Rw6选自氢、卤素、C1-C4烷基或C1-C4卤代烷基;
且其中Het为Het-1或Het-11a:
其中#表示式(I)中的键,且其中R6a选自氢、卤素或C1-C4卤代烷基;
R1、R2都为氢;
X选自O或S;
且其中进一步:
R3a、R3b相互独立地选自氢或氟;
p为0;
Y为为S(O)m,其中m为0、1或2;
且
R5为未被取代或者部分或完全卤代的C1-C3烷基。
优选和尤其优选的式I化合物的实例在下文中给出。
一般而言,优选的本发明化合物为下文所述式I-A.0至I-P.2的化合物,其中Het、R1、R2R3a、R3b和R5具有上文给出的含义。
尤其优选的下文所述式(I-A.0)至式(I-P.2)化合物为其中Het、R1、R2R3a、R3b和R5具有下表C的第1-784行中任一行给出的含义的那些。
这类尤其优选的化合物的实例为式(I-A.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-A.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-A.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-B.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-B.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-B.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-C.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-C.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-C.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-D.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-D.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-D.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-E.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-E.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-E.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-F.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-F.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-F.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-G.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-G.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-G.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-H.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-H.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-H.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-I.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-I.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-I.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-J.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-J.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-J.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-K.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-K.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-K.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-L.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-L.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-L.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-M.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-M.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-M.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-N.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-N.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-N.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-O.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-O.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-O.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-P.0)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-P.1)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
这类尤其优选的化合物的实例为式(I-P.2)化合物,其中Het、R1、R2R3a、R3b和R5具有表C的第1-784行中任一行中给出的含义。
表C:
*其中#表示与分子其余部分的键。
例如,以下尤其优选的化合物N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2-甲硫基-乙酰胺:
在表C中由式I-M.0的化合物C.1表示。
此外,关于表中那些单独变量提到的以及更前面提到的含义本身为所述取代基的特别优选实施方案,不依赖于提到它们的组合。
制备方法
本发明式(I)化合物可例如根据如下所述制备方法和制备方案制备。
本发明式(I)化合物可通过有机化学的标准方法,例如通过如下所述制备方法和制备方案制备。方案中给出的分子结构的Het、x、Y、R1、R2、R3a、R3b、R4a、R4b和R5的定义如上文所定义。室温意指约20-25℃的温度范围。
制备式(I)化合物的一般方法的实例在下文中显示于方案A中。因此,存在于式(I)化合物中的吡啶元素3的结构可例如通过将合适的2-氨基吡啶基前体1用合适的式2试剂烷基化而得到。转化优选在极性溶剂如乙腈、丙酮、二氯甲烷、四氢呋喃、N,N-二甲基甲酰胺或C1-C6醇中在室温至溶剂的回流温度之间进行。将类似于式1的吡啶前体烷基化的代表性反应条件在Tett.Lett.2011,52(23),3033-3037中给出。式5前体的合成可通过使用就地活化的酸4将式3化合物中的吡啶氮酰化而得到。该转化优选在极性溶剂如乙腈、丙酮、四氢呋喃、N,N-二甲基甲酰胺中,或者在惰性溶剂如二氯甲烷、1,2-二氯乙烷或1,2-二甲氧基乙烷中,在室温至溶剂的回流温度之间的温度下进行。将2-取代吡啶酰化的代表性程序条件在Journal of Medicinal Chemistry,1988,31,4,807-814中给出。式2和4中的合适离去基团(LG)的实例包括但不限于卤素、烷基磺酸酯、卤代烷基磺酸酯、烷基膦酸酯以及衍生自游离碳酸与肽偶联试剂在胺碱的存在下反应的各种活化酯。这两个步骤的颠倒也会产生可接受的所需化合物合成。在Y为S的情况下,硫原子可通过以下标准反应条件使用mCPBA、H2O2和NaIO4作为末端氧化剂(oxident)而氧化成亚砜或砜。代表性的氧化程序可在TetrahedronLetters,1982,23,22,2269-2272或Journal of Heterocyclic Chemistry,1978,15,1361-1366中找到。
方案A:
制备子类9的式(I)化合物的一般方法的实例显示于方案B中。结构类型9的化合物表示其中p=0的式(I)化合物的子结构。可使用对5的合成所述的条件将如上文在方案A中所述制备的化合物3的溶液用试剂6酰化以提供类别7的化合物。LG2的选择包括但不限于:氯、溴、碘、烷基磺酸酯和芳基磺酸酯。在随后的反应中,亲核体8置换LG2产生所需的化合物9。该反应理想地在极性溶剂如乙腈、丙酮、二甲亚砜、N,N-二甲基甲酰胺、N,N-甲基乙酰胺、N-甲基吡咯烷酮或二甲氧基乙烷中,在室温至溶剂的回流温度之间的温度下,在碱如氢化锂、氢化钠、氢化钾、碳酸钾、碳酸钠、碳酸锂、碳酸氢钠、叔丁醇钾、叔丁醇钠、叔丁醇锂的存在下进行。代表性的程序可在Journal of Medicinal Chemistry,2003,46,12,2361-2375中找到。
方案B:
用于制备子类12的式(I)化合物的一般方法的实例显示于方案C中。结构类型12的化合物表示其中p=1的式(I)化合物的子结构。可使用对5的合成描述的条件将如上文在方案A中所述制备的化合物3的溶液用试剂10酰化以提供类别11的化合物。化合物10中的LG的选择包括但不限于:氯、溴、碘、烷基磺酸酯和芳基磺酸酯。在随后的反应中,亲核体8加成到11中的烯烃上产生所需化合物12。反应最佳地在惰性或极性溶剂:二氯甲烷、四氢呋喃、1,2-二氯乙烷、1,2-二甲氧基乙烷、1,4-二烷、二甲亚砜、N,N-二甲基甲酰胺、N,N-甲基乙酰胺、N-甲基吡咯烷酮、水中,在碱如三乙胺、二异丙基乙胺、吡啶、哌啶、三甲基苄基氢氧化物、碳酸钾、碳酸钠、碳酸锂或碳酸氢钠的存在下进行。反应在0℃至溶剂的回流温度之间的温度下进行。代表性程序可在Journal of the American Chemical Society,2008,130,16295-16309中找到。
方案C:
如果各个化合物不能借助上述路线制备,则它们可通过将其它化合物(I)衍生化或者通过常规改变所述合成路线而制备。
将反应混合物以常规方式后处理,例如通过与水混合,分离相并且如果合适的话通过色谱法,例如在氧化铝或硅胶上提纯粗产物而后处理。一些中间体和最终产物可以以无色或浅褐色粘性油的形式获得,在降低的压和适当升高的温度下除去或纯化掉挥发性组分。如果中间体和最终产物以固体得到,则它们可通过再结晶或浸提来纯化。
害虫
式I化合物及其盐特别适于有效地防治节肢动物害虫如蜘蛛类、多足类和昆虫以及线虫。
式I化合物尤其适于有效地对抗以下害虫:
鳞翅目昆虫(鳞翅目(Lepidoptera)),例如桑剑纹夜蛾(Acronicta major)、茶小卷叶蛾(Adoxophyes orana)、三条伊蚊(Aedia leucomelas),地老虎属(Agrotis spp.),例如燕青地老虎(Agrotis fucosa)、黄地老虎(Agrotis segetum)、小地老虎(Agrotisypsilon);棉叶波纹夜蛾(Alabama argillacea)、黎豆夜蛾(Anticarsia gemmatalis)、干煞夜蛾属(Anticarsia spp.)、Argyresthia conjugella、叉纹夜蛾(Autographa gamma)、甘蓝夜蛾(Barathra brassicae)、棉潜蛾(Bucculatrix thurberiella)、树尺蠖(Bupaluspiniarius)、Cacoecia murinana、卷叶蛾(Cacoecia podana)、Capua reticulana、苹果蠹蛾(Carpocapsa pomonella)、Cheimatobia brumata,二化螟属(Chilo spp.),例如二化螟(Chilo suppressalis);云杉色卷蛾(Choristoneura fumiferana)、Choristoneuraoccidentalis、Cirphis unipuncta、葡萄果蠹蛾(Clysia ambiguella)、Cnaphalocerusspp.、苹果小卷蛾(Cydia pomonella)、欧洲松毛虫(Dendrolimus pini)、Diaphanianitidalis、西南玉米杆草螟(Diatraea grandiosella)、埃及钻夜蛾(Earias insulana)、南美玉米苗斑螟(Elasmopalpus lignosellus)、粉斑螟蛾(Ephestia cautella)、地中海斑螟(Ephestia kuehniella)、女贞细卷蛾(Eupoecilia ambiguella)、Euproctischrysorrhoea、切叶蛾属(Euxoa spp.)、Evetria bouliana,褐夜蛾属(Feltia spp.),例如Feltia subterranean;蜡螟(Galleria mellonella)、李小食心虫(Grapholithafunebrana)、梨小食心虫(Grapholitha molesta),铃夜蛾属(Helicoverpa spp.),例如Helicoverpa armigera、美洲棉铃虫(Helicoverpa zea);棉铃虫属(Heliothis spp.),例如棉铃虫(Heliothis armigera)、烟芽夜蛾(Heliothis virescens)、玉米穗虫(Heliothiszea);菜螟(Hellula undalis)、Hibernia defoliaria、拟衣蛾(Hofmannophilapseudospretella)、茶长卷叶蛾(Homona magnanima)、美国白蛾(Hyphantria cunea)、苹果巢蛾(Hyponomeuta padella)、Hyponomeuta malinellus、番茄虫蛾(Keiferialycopersicella)、Lambdina fiscellaria,甜菜夜蛾属(Laphygma spp.),例如甜菜夜蛾(Laphygma exigua);咖啡潜叶蛾(Leucoptera coffeella)、旋纹潜蛾(Leucopterascitella)、Lithocolletis blancardella、绿果冬夜蛾(Lithophane antennata)、葡萄浆果小卷蛾(Lobesia botrana)、Loxagrotis albicosta、甜菜网螟(Loxostegesticticalis),毒蛾属(Lymantria spp.),例如舞毒蛾(Lymantria dispar)、模毒蛾(Lymantria monacha);桃潜蛾(Lyonetia clerkella)、黄褐天幕毛虫(Malacosomaneustria),甘蓝夜蛾属(Mamestra spp.),例如甘蓝夜蛾(Mamestra brassicae);Mocisrepanda、粘虫(Mythimna separata)、黄杉毒蛾(Orgyia pseudotsugata)、Oria spp.,秆野螟属(Ostrinia spp.),例如玉米螟(Ostrinia nubilalis);水稻负泥虫(Oulema oryzae)、小眼夜蛾(Panolis flammea),Pectinophora spp.,例如Pectinophora gossypiella;疆夜蛾(Peridroma saucia)、圆掌舟蛾(Phalera bucephala),Phthorimaea spp.,例如马铃薯麦蛾(Phthorimaea operculella);柑桔潜叶蛾(Phyllocnistis citrella),粉蝶属(Pieris spp.),例如欧洲粉蝶(Pieris brassicae)、菜青虫(Pieris rapae);苜蓿绿夜蛾(Plathypena scabra)、菜蛾(Plutella maculipennis)、菜蛾(Plutella xylostella),Prodenia spp.,Pseudaletia spp.、大豆夜蛾(Pseudoplusia includens)、Pyraustanubilalis、Rhyacionia frustrana、Scrobipalpula absoluta、麦蛾(sitotrogacerealella)、葡萄卷叶蛾(Sparganothis pilleriana),斜纹夜蛾属(Spodoptera spp.),例如草地夜蛾(Spodoptera frugiperda)、海灰翅夜蛾(Spodoptera littoralis)、斜纹夜蛾(Spodoptera litura);Thaumatopoea pityocampa、Thermesia gemmatalis、袋衣蛾(Tinea pellionella)、衣蛾(Tineola bisselliella)、绿色橡木飞蛾(Tortrixviridana),粉纹夜蛾属(Trichoplusia spp.),例如粉纹夜蛾(Trichoplusia ni);Tutaabsoluta和Zeiraphera canadensis,
甲虫(鞘翅目(Coleoptera)),例如Acanthoscehdes obtectus、像丽金龟属(Adoretus spp.)、杨树萤叶甲(Agelastica alni)、梨窄吉丁(Agrilus sinuatus),细胸金针虫属(Agriotes spp.),例如细胸金针虫(Agriotes fuscicollis)、直条叩头虫(Agriotes lineatus)、暗色叩头虫(Agriotes obscurus);Amphimallus solstitialis、Anisandrus dispar、具斑窃蠹(Anobium punctatum)、红铜丽金龟(Anomala rufocuprea),星天牛属(Anoplophora spp.),例如Anoplophora glabripennis;花象属(Anthonomusspp.),例如墨西哥棉铃象(Anthonomus grandis)、苹花象(Anthonomus pomorum);圆皮蠹属(Anthrenus spp.)、Aphthona euphoridae、阿鱼思金龟属(Apogonia spp.)、Athoushaemorrhoidalis,隐翅甲属(Atomaria spp.),例如甜菜隐食甲(Atomaria linearis);毛蠹属(Attagenus spp.)、黄守瓜(Aulacophora femoralis)、纵坑切梢小蠹(Blastophaguspiniperda)、Blitophaga undata、豆象(Bruchidius obtectus),豆象属(Bruchus spp.),例如欧洲兵豆象(Bruchus lentis)、豌豆象(Bruchus pisorum)、蚕豆象(Bruchusrufimanus);苹卷象(Byctiscus betulae)、绿豆象(Callosobruchus chinensis)、甜菜大龟甲(Cassida nebulosa)、Cerotoma trifurcata、金花金龟(Cetonia aurata),龟象属(Ceuthorhynchus spp.),例如白菜籽龟象(Ceuthorrhynchus assimilis)、芫菁龟象(Ceuthorrhynchus napi);甜菜胫跳甲(Chaetocnema tibialis)、Cleonus mendicus,宽胸叩头虫属(Conoderus spp.),例如Conoderus vespertinus;根颈象属(Cosmopolitesspp.)、Costelytra zealandica、石刁柏负泥虫(Crioceris asparagi)、杨干象(Cryptorhynchus lapathi),Ctenicera ssp.,例如Ctenicera destructor;象鼻虫属(Curculio spp.)、Dectes texanus、皮蠹属(Dermestes spp.),叶甲属(Diabroticaspp.),例如Diabrotica 12-punctata、南美叶甲(Diabrotica speciosa)、Diabroticalongicornis、Diabrotica semipunctata、玉米根叶甲(Diabrotica virgifera);食植瓢虫属(Epilachna spp.),例如墨西哥豆瓢虫(Epilachna varivestis)、马铃薯瓢虫(Epilachna vigintioctomaculata);跳甲属(Epitrix spp.),例如烟草跳甲(Epitrixhirtipennis);Eutinobothrus brasiliensis、烟草钻孔虫(Faustinus cubae)、裸蛛甲(Gibbium psylloides)、黑异爪蔗金龟(Heteronychus arator)、Hylamorpha elegans、欧洲松树皮象(Hylobius abietis)、北美家天牛(Hylotrupes bajulus)、埃及苜蓿叶象(Hypera brunneipennis)、紫苜蓿叶象(Hypera postica),小蠹属(Hypothenemus spp.)、云杉八齿小蠹(Ips typographus)、甘蔗大褐齿爪總金龟(Lachnosterna consanguinea)、烟草负泥虫(Lema bilineata)、黑角负泥虫(Lema melanopus),Leptinotarsa spp.,例如马铃薯叶甲(Leptinotarsa decemlineata);Limonius californicus、稻水象甲(Lissorhoptrus oryzophilus)、稻水象甲(Lissorhoptrus oryzophilus)、筒味象属(Lixus spp.),粉蠹属(Lyctus spp.),例如褐粉蠹(Lyctus bruneus);Melanotuscommunis、Meligethes spp.,例如油菜露尾甲(Meligethes aeneus);大栗鳃金龟(Melolontha hippocastani)、五月鳃金龟(Melolontha melolontha),Migdolus spp.,墨天牛属(Monochamus spp.),例如松褐天牛(Monochamus alternatus);象甲(Naupactusxanthographus)、黄蛛甲(Niptushololeucus)、椰犀角金龟子(Oryctes rhinoceros)、锯谷盗(Oryzaephilus surinamensis)、黑葡萄耳象(Otiorrhynchus sulcatus)、草莓根象甲(Otiorrhynchus ovatus)、黑葡萄耳象(Otiorrhynchus sulcatus)、水稻负泥虫(Oulemaoryzae)、小青花金龟(Oxycetoniajucunda)、辣根猿叶甲(Phaedon cochleariae)、梨树叶象(Phyllobius pyri)、庭园发丽金龟(Phyllopertha horticola),食叶鳃金龟属(Phyllophaga spp.),跳甲属(Phyllotreta spp.),例如Phyllotreta chrysocephala、大豆淡足跳甲(Phyllotreta nemorum)、黄曲条菜跳甲(Phyllotreta striolata);食叶鳃金龟属(Phyllophaga spp.)、庭园发丽金龟(Phyllopertha horticola)、日本金龟子(Popillia japonica),Premnotrypes spp.,油菜蚤跳甲(Psylliodes chrysocephala),蛛甲属(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizopertha dominica)、豌豆叶象(Sitona lineatus)、谷象属(Sitophilus spp.),例如谷象(Sitophilusgranaria)、玉米象(Sitophilus zeamais);尖隐味象属(Sphenophorus spp.),例如Sphenophorus levis;莲干象属(Sternechus spp.),例如Sternechus subsignatus;Symphyletes spp.、黄粉虫(Tenebrio molitor),拟谷盗属(Tribolium spp.),例如赤拟谷盗(Tribolium castaneum);斑皮蠹属(Trogoderma spp.),籽象属(Tychius spp.)、脊虎天牛属(Xylotrechus spp.)和距步甲属(Zabrus spp.),例如Zabrus Tenebrioides,
来自双翅目(Diptera)的飞虫,例如伊蚊属(Aedes spp.),例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、剌扰伊蚊(Aedes vexans);墨西哥果蝇(Anastrepha ludens)、按蚊属(Anopheles spp.),例如白足按蚊(Anopheles albimanus)、Anopheles crucians、Anopheles freeborni、冈比亚按蚊(Anopheles gambiae)、海南岛白踝按蚊(Anopheles leucosphyrus)、五斑按蚊(Anopheles maculipennis)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anopheles quadrimaculatus)、中华按蚊(Anophelessinensis);全北毛蚊(Bibio hortulanus)、红头丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina)、Cerafitis capitata、地中海实蝇(Ceratitis capitata)、金蝇属(Chrysomyia spp.),例如蛆症金蝇(Chrysomya bezziana)、Chrysomya hominivorax、Chrysomya macellaria;Chrysops atlanticus、鹿蝇(Chrysops discalis)、Chrysopssilacea、锥蝇属(Cochliomyia spp.),例如螺旋蝇(Cochliomyia hominivorax);瘦蚊属(Contarinia spp.),例如高粱瘿蚊(Contarinia sorghicola);Cordylobiaanthropophaga、库蚊属(Culex spp.),例如斑蚊(Culex nigripalpus)、尖音库蚊(Culexpipiens)、致倦库蚊(Culex quinquefasciatus)、煤斑蚊(Culex tarsalis)、Culextritaeniorhynchus;狂怒库蠓(Culicoides furens)、Culiseta inornata、Culisetamelanura、黄狂蝇属(Cuterebra spp.)、瓜蝇(Dacus cucurbitae)、油橄榄实蝇(Dacusoleae)、油菜叶瘿蚊(Dasineura brassicae)、Delia spp.,例如Delia antique、麦地种蝇(Delia coarctata)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum);Dermatobia hominis、果蝇(Drosophila spp.)、Fannia spp.,例如小毛厕蝇(Fanniacanicularis);Gastraphilus spp.,例如马蝇(Gasterophilus intestinalis);GeomyzaTripunctata、Glossina fuscipes、刺舌蝇(Glossina morsitans)、须舌蝇(Glossinapalpalis)、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosisequestris、潜蝇属(Hippelates spp.)、黑蝇属(Hylemyia spp.),例如花生田灰地种蝇(Hylemyia platura);牛蝇属(Hypoderma spp.),例如纹皮蝇(Hypoderma lineata);Hyppobosca spp.、Leptoconops torrens、斑潜蝇(Liriomyza spp.),例如蔬菜斑潜蝇(Liriomyza sativae)、美国潜叶蝇(Liriomyza trifolii);绿蝇属(Lucilia spp.),例如Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Lucilia sericata);Lycoriapectoralis、Mansonia titillanus、麦瘿蚊属(Mayetiola spp.),例如麦瘿蚊(Mayetioladestructor);家蝇属(Musca spp.),例如秋家蝇(Musca autumnalis)、家蝇(Muscadomestica);厩腐蝇(Muscina stabulans)、狂蝇属(Oestrus spp.),例如羊狂蝇(Oestrusovis);Opomyza florum、Oscinella spp.,例如欧洲麦秆蝇(Oscinella frit);天仙子泉蝇(Pegomya hysocyami)、银足白蛉(Phlebotomus argentipes)、Phorbia spp.,例如Phorbiaantiqua、萝卜蝇(Phorbia brassicae)、Phorbia coarctata;Prosimulium mixtum、胡萝卜茎蝇(Psila rosae)、Psorophora columbiae、Psorophora discolor、樱桃实蝇(Rhagoletiscerasi)、苹果实蝇(Rhagoletis pomonella)、麻蝇属(Sarcophaga spp.),例如赤尾麻蝇(Sarcophaga haemorrhoidalis);Simulium vittatum、螫蝇属(Stomoxys spp.),例如厩螫蝇(Stomoxys calcitrans);虻属(Tabanus spp.),例如Tabanus atratus、Tabanusbovinus、红色原虻(Tabanus lineola)、Tabanus similis;Tannia spp.、Tipulaoleracea、欧洲大蚊(Tipula paludosa)和污蝇属(Wohlfahrtia spp.),
蓟马(缨翅目(Thysanoptera)),例如稻蓟马(Baliothrips biformis)、兰花蓟马(Dichromothrips corbetti)、Dichromothrips ssp.、Enneothrips flavens、花蓟马属(Frankliniella spp.),例如烟褐蓟马(Frankliniella fusca)、苜蓿花蓟马(Frankliniella occidentalis)、东方花蓟马(Frankliniella tritici);实夜蛾属(Heliothrips spp.)、温室蓟马(Hercinothrips femoralis)、卡蓟马属(Kakothripsspp.)、Rhipiphorothrips cruentatus、硬蓟马属(Scirtothrips spp.),例如桔硬蓟马(Scirtothrips citri);Taeniothrips cardamoni、蓟马属(Thrips spp.),例如稻蓟马(Thrips oryzae)、棕榈蓟马(Thrips palmi)和烟蓟马(Thrips tabaci),
白蚁(等翅目(Isoptera)),例如Calotermes flavicollis、台湾乳白蚁(Coptotermes formosanus)、金黄异白蚁(Heterotermes aureus)、Heterotermeslongiceps、Heterotermes tenuis、Leucotermes flavipes、土白蚁属(Odontotermesspp.)、散白蚁属(Reticulitermes spp.),例如黄胸散白蚁(Reticulitermes speratus)、黄肢散白蚁(Reticulitermes flavipes)、Reticulitermes grassei、欧洲散白蚁(Reticulitermes lucifugus)、桑特散白蚁(Reticulitermes santonensis)、美小黑散白蚁(Reticulitermes virginicus);Termes natalensis,
蟑螂(蜚蠊目(Blattaria-Blattodea)),例如居屋艾蟋(Acheta domesticus)、东方蜚蠊(Blatta orientalis)、Blattella asahinae、德国小蠊(Blattella germanica)、蝼蛄属(Gryllotalpa spp.)、Leucophaea maderae、飞蝗属(Locusta spp.)、黑蝗属种(Melanoplus spp.)、美洲蟑螂(Periplaneta americana)、澳洲蜚蠊(Periplanetaaustralasiae)、棕色蜚蠊(Periplaneta brunnea)、Periplaneta fuligginosa、日本大蠊(Periplaneta japonica),
臭虫、蚜虫、叶蝉、烟粉虱、介壳虫、臭虫(半翅目(Hemiptera)),例如Acrosternumspp.,例如拟绿蝽(Acrosternum hilare);Acyrthosipon spp.,例如Acyrthosiphononobrychis、豌豆蚜(Acyrthosiphon pisum);落叶松球蚜(Adelges laricis)、Aeneolamiaspp.、Agonoscena spp.、Aleurodes spp.、Aleurolobus barodensis、Aleurothrixusspp.、Amrasca spp.、南瓜缘蝽(Anasa tristis)、拟丽蝽属(Antestiopsis spp.)、飞廉短尾虫牙(Anuraphis cardui)、蹄盾蚧属(Aonidiella spp.)、梨瘤蚜(Aphanostigma piri)、Aphidula nasturtii、蚜属(Aphis spp.),例如甜菜蚜(Aphis fabae)、草莓根蚜(Aphisforbesi)、棉蚜(Aphis gossypii)、北美茶簏子蚜(Aphis grossulariae)、苹果蚜(Aphispomi)、Aphis sambuci、希奈德蚜(Aphis schneideri)、卷叶蚜(Aphis spiraecola);葡萄叶蝉(Arboridia apicalis)、Arilus critatus、Aspidiella spp.、Aspidiotus spp.、Atanus spp.、马铃薯蚜(Aulacorthum solani)、烟属(Bemisia spp.),例如银叶粉虱(Bemisia argentifolii)、烟粉虱(Bemisia tabaci);Blissus spp.,例如玉米长蝽(Blissus leucopterus);Brachycaudus cardui、杏圆尾蚜(Brachycaudus helichrysi)、Brachycaudus persicae、Brachycaudus prunicola、Brachycolus spp.、甘蓝蚜(Brevicoryne brassicae)、小褐稻虱(Calligypona marginata)、俊盲蝽属(Calocorisspp.)、Campylomma livida、Capitophorus horni、Carneocephala fulgida、异背长蝽属(Cavelerius spp.)、Ceraplastes spp.、Ceratovacuna lanigera、沫蝉科(Cercopidae)、Cerosipha gossypii、Chaetosiphon fragaefolii、蔗黄雪盾蜂(Chionaspistcgalensis)、茶绿叶蜂(Chlorita onukii)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalus ficus)、Cicadulina mbila、臭虫属(Cimex spp.),例如热带臭虫(Cimex hemipterus)、温带臭虫(Cimex lectularius);Coccomytilus halli、球菌属(Coccus spp.)、绿盲蝽(Creontiades dilutus)、Cryptomyzus ribis、Cryptomyzusribis、黑斑烟盲蝽(Cyrtopeltis notatus)、Dalbulus spp.、胡椒缘蝽(Dasynuspiperis)、Dialeurades spp.、Diaphorina spp.、Diaspis spp.、Dichelops furcatus、Diconocoris hewetti、Doralis spp.、高加索冷杉椎球蚜(Dreyfusia nordmannianae)、云杉椎球蚜(Dreyfusia piceae)、履棉蚧属(Drosicha spp.)、Dysaphis spp.,例如Dysaphisplantaginea、Dysaphis pyri、居根西圆尾蚜(Dysaphis radicola);Dysaulacorthumpseudosolani、红蝽(Dysdercus spp.),例如棉红蝽(Dysdercus cingulatus)、Dysdercusintermedius;灰粉阶属(Dysmicoccus spp.)、叶蝉属(Empoasca spp.),例如蚕豆微叶蝉(Empoasca fabae)、南方浮尘子(Empoasca solana);Eriosoma spp.、小叶蝉属(Erythroneura spp.)、Eurygaster spp.,例如麦扁盾蝽(Eurygaster integriceps);殃叶蝉(Euscelis bilobatus)、Euschistus spp.,例如Euschistuos heros、Euschistusimpictiventris、Euschistus servus;咖啡地粉蚁(Geococcus coffeae)、Halyomorphaspp.,例如茶翅蝽(Halyomorpha halys);Heliopeltis spp.、Homalodisca coagulata、Horcias nobilellus、桃大尾蚜(Hyalopterus pruni)、Hyperomyzus lactucae、吹绵蚧属(Icerya spp.)、片角叶蝉属(Idiocerus spp.)、叶蝶属(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、Lecanium spp.、Lepidosaphes spp.、Leptocorisa spp.、棉红铃喙缘蝽(Leptoglossus phyllopus)、萝卜蚜(Lipaphis erysimi)、棉盲蝽(Lygusspp.),例如豆荚草盲蝽(Lygus hesperus)、美洲牧草盲蝽(Lygus lineolaris)、牧草盲蝽(Lygus pratensis);Macropes excavatus、Macrosiphum spp.,例如蔷薇长管蚜(Macrosiphum rosae)、麦长管蚜(Macrosiphum avenae)、大戟长管蚜(Macrosiphumeuphorbiae);Mahanarva fimbriolata、筛豆龟蝽(Megacopta cribraria)、Megouraviciae、巢莱修尾蚜(Melanaphis pyrarius)、高粱蚜(Melanaphis sacchari)、Metcafiella spp.、麦无网蚜(Metopolophium dirhodum)、Miridae spp.、黑缘平翅斑姆(Monellia costalis)、Monelliopsis pecanis、Myzus spp.,例如冬葱瘤额蚜(Myzusascalonicus)、Myzus cerasi、桃蚜(Myzus persicae)、李瘤蚜(Myzus varians);Nasonovia ribis-nigri、浮尘子属(Nephotettix spp.,例如Nephotettix malayanus、黑尾叶蝉(Nephotettix nigropictus)、细小黑尾叶蝉(Nephotettix parvus)、二点黑尾叶蝉(Nephotettix virescens);绿蝽(Nezara spp.),例如稻绿蝽(Nezara viridula);稻飞虱(Nilaparvata lugens)、Oebalus spp.、Oncometopia spp.、Orthezia praelonga、Parabemisia myricae、木虱(Paratrioza spp.)、黑点蚧(Parlatoria spp.)、瘿绵蚜属(Pemphigus spp.),例如囊柄瘿绵蚜(Pemphigus bursarius);Pentomidae、玉米蜡蝉(Peregrinus maidis)、蔗飞虱(Perkinsiella saccharicida)、绵粉蚧(Phenacoccusspp.)、Phloeomyzus passerinii、忽布疣蚜(Phorodon humuli)、根瘤蚜属(Phylloxeraspp)、甜菜拟网蝽(Piesma quadrata)、Piezodorus spp.,例如Piezodorus guildinii、百合并盾虫介(Pinnaspis aspidistrae)、臀纹粉蚧属(Planococcus spp.)、梨形圆棉蚧(Protopulvinaria pyriformis)、棉跳盲蝽(Psallus seriatus)、Pseudacysta persea、桑盾蚧(Pseudaulacaspis pentagona)、粉蚧属(Pseudococcus spp.),例如康氏粉蚧(Pseudococcus comstocki);木虱属(Psylla spp.),例如苹木虱(Psylla mali)、梨木虱(Psylla piri);金小蜂属(Pteromalus spp.)、Pyrilla spp.、Quadraspidiotus spp.、Quesada gigas、Rastrococcus spp.、Reduvius senilis、红猎蝽属(Rhodnius spp.)、冬葱瘤蛾蚜(Rhopalomyzus ascalonicus)、缢管蚜属(Rhopalosiphum spp.),例如Rhopalosiphum pseudobrassicas、Rhopalosiphum insertum、玉米蚜(Rhopalosiphummaidis)、禾谷溢管蚜(Rhopalosiphum padi);Sagatodes spp.、可可斑褐盲蝽(Sahlbergella singularis)、黑盔蚧属(Saissetia spp.)、Sappaphis mala、Sappaphismali、Scaphoides titanus、麦二叉蚜(Schizaphis graminum)、Schizoneura lanuginosa、漂虫舂属(Scotinophora spp.)、Selenaspidus articulatus、麦长管蚜(sitobionavenae)、Sogata spp.、白背飞虱(Sogatella furcifera)、Solubea insularis、梨网蝽(Stephanitis nashi)、三角蝶(Stictocephala festina)、Tenalaphara malayensis、Thyanta spp.,例如Thyanta perditor;Tibraca spp.、美国核桃黑蚜(Tinocalliscaryaefoliae)、Tomaspis spp.、Toxoptera spp.,例如Toxoptera aurantii;粉虱属(Trialeurodes spp.),例如白粉虱(Trialeurodes vaporariorum);Triatoma spp.、Trioza spp.、小叶蝉属(Typhlocyba spp.)、Unaspis spp.,例如矢尖蚧(Unaspisyanonensis);和葡萄根瘤蚜(Viteus vitifolii),
蚂蚁、蜜蜂、黄蜂、锯蝇(膜翅目(Hymenoptera)),例如新疆菜叶蜂(Athaliarosae)、Atta capiguara、切叶蚁(Atta cephalotes)、切叶蚁(Atta cephalotes)、Attalaevigata、Atta robusta、Atta sexdens、Atta texana、熊蜂属(Bombus spp.)、Camponotus floridanus、举腹蚁属(Crematogaster spp.)、天鹅绒蚂蚁(Dasymutillaoccidentalis)、松锯蜂属(Diprion spp.)、姬胡蜂(Dolichovespula maculata)、实蜂属(Hoplocampa spp.),例如Hoplocampa minuta、Hoplocampa testudinea;Lasius spp.,例如黑毛蚁(Lasius niger)、阿根廷蚁(Linepithema humile)、小黄家蚁(Monomoriumpharaonis)、Paravespula germanica、Paravespula pennsylvanica、Paravespulavulgaris、Pheidole megacephala、红蚂蚁(Pogonomyrmex barbatus)、Pogonomyrmexcalifornicus、胡蜂(Polistes rubiginosa)、热带火蚁(Solenopsis geminata)、红火蚁(Solenopsis invicta)、黑火蚁(Solenopsis richteri)、南方火蚁(solenopsis xyloni)、胡蜂属(Vespa spp.),例如黄边胡蜂(Vespa crabro)和大黄蜂(Vespula squamosa),
蟋蟀、蚱蜢、蝗虫(直翅目(Orthoptera)),例如居屋艾蟋(Acheta domestica)、意大利蝗(Calliptamus italicus)、澳洲草栖蝗(Chortoicetes terminifera)、摩洛哥戟纹蝗(Dociostaurus maroccanus)、非洲蝼蛄(Gryllotalpa africana)、蝼蛄(Gryllotalpagryllotalpa)、非洲蔗蝗(Hieroglyphus daganensis)、Kraussaria angulifera、飞蝗(Locusta migratoria)、褐色拟飞蝗(Locustana pardalina)、双纹黑蝗(Melanoplusbivittatus)、红足黑蝗(Melanoplus femurrubrum)、墨西哥黑蝗(Melanoplusmexicanus)、迁飞黑蝗(Melanoplus sanguinipes)、石栖黑蝗(Melanoplus spretus)、条纹红蝗(Nomadacris septemfasciata)、塞纳加尔小车蝗(Oedaleus senegalensis)、美洲沙漠蝗(Schistocerca americana)、沙漠蝗(Schistocerca gregaria)、庭疾灶螽(Tachycines asynamorus)和Zonozerus variegatus,
蜘蛛纲(蜱螨目(Arachnida)),例如蜱螨,如软蜱科(Argasidae)、硬蜱科(Ixodidae)和疥螨科(Sarcoptidae),例如Amblyomma spp.(例如长星形壁虱(Amblyommaamericanum)、热带花蜱(Amblyomma variegatum)、Amblyomma maculatum)、锐缘蜱属(Argas spp.)(例如波斯锐缘蜱(Argas persicus))、牛蜱属(Boophilus spp.)(例如牛壁虱(Boophilus annulatus)、Boophilus decoloratus、微小牛蜱(Boophilus microplus))、Dermacentor silvarum、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentorvariabilis)、璃眼蜱属(Hyalomma spp.)(例如Hyalomma truncatum)、Ixodes spp.(例如蓖子硬蜱(Ixodes ricinus)、Ixodes rubicundus、黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus))、钝缘蜱属(Ornithodorusspp.).(例如Ornithodorus moubata、Ornithodorus hermsi、Ornithodorus turicata)、柏氏禽刺螨(Ornithonyssus bacoti)、Otobius megnini、鸡皮刺螨(Dermanyssusgallinae)、痒螨属(Psoroptes spp.)(例如绵羊疥病(Psoroptes ovis))、Rhipicephalusspp.(例如Rhipicephalus sanguineus、Rhipicephalus appendiculatus、Rhipicephalusevertsi)、根嗜螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)(例如人疥螨(Sarcoptes scabiei))和瘿螨属(Eriophyidae spp.),例如Acaria sheldoni、Aculopsspp.(例如Aculops pelekassi),刺绣螨属(Aculus spp.)(例如苹果刺锈螨(Aculusschlechtendali))、Epitrimerus pyri、Phyllocoptruta oleivora,和瘦螨属(Eriophyesspp.)(例如Eriophyes sheldoni);细螨属(Tarsonemidae spp.),例如半跗线螨属(Hemitarsonemus spp.)、Phytonemus pallidus和侧多食跗线螨(Polyphagotarsonemuslatus)、狭足付线螨属(Stenotarsonemus spp.);细须螨属(Tenuipalpidae spp.),例如短须螨属(Brevipalpus spp.)(例如紫红短须螨(Brevipalpus phoenicis));叶螨属(Tetranychidae spp.),例如始叶螨属(Eotetranychus spp.)、真叶螨属(Eutetranychusspp.)、小爪觸属(Oligonychus spp.)、朱砂叶螨(Tetranychus cinnabarinus)、神泽叶螨(Tetranychus kanzawai)、太平洋叶螨(Tetranychus pacificus)、棉叶螨(Tetranychustelarius)和二点叶螨(Tetranychus urticae);Bryobia praetiosa、全爪螨属(Panonychus spp.)(例如苹果叶螨(Panonychus ulmi)、柑椐叶螨(Panonychus citri))、Metatetranychus spp.和小爪觸属(Oligonychus spp.)(例如Oligonychus pratensis)、Vasates lycopersici;蜘蛛目(Araneida),例如毒蜘蛛(Latrodectus mactans)和褐丝蛛(Loxosceles reclusa),和脚粉螨(Acarus siro)、足螨属(Chorioptes spp.)、蝎(Scorpiomaurus),
跳蚤(蚤目(Siphonaptera)),例如角叶蚤属(Ceratophyllus spp.)、猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(xenopsyllacheopis)、致痒蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyllus fasciatus)
衣鱼、家衣鱼(缨尾目(Thysanura)),例如衣鱼(Lepisma saccharina)和斑衣鱼(Thermobia domestica),
百足虫(唇足纲(Chilopoda)),例如地蜈松属(Geophilus spp.)、蚰蜒(Scutigeraspp.),例如Scutigera coleoptrata;
千足虫(倍足纲(Diplopoda)),例如Blaniulus guttulatus、Narceus spp.,
蠼蛸(革翅目(Dermaptera)),例如欧洲球螋(forficula auricularia),
虱(毛虱目(Phthiraptera)),例如畜虱属(Damalinia spp.)、人虱属(Pediculusspp.),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanuscorporis);阴虱(Pthirus pubis)、血虱属(Haematopinus spp.),例如牛血虱(Haematopinus eurysternus)、猪血虱(Haematopinus suis);颚虱属(Linognathusspp.),例如牛颚虱(Linognathus vituli);Bovicola bovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus、啮毛虱属(Trichodectes spp.),
跳虫(弹尾目(Collembola)),例如Onychiurus ssp.,例如Onychiurus armatus。
它们还适于防治线虫:植物寄生线虫如根结线虫,北方根结线虫(Meloidogynehapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)和其他根结线虫属(Meloidogyne);形成胞囊的线虫,马铃薯金线虫(Globoderarostochiensis)和其他球胞囊属(Globodera);谷胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)和其他胞囊线虫属(Heterodera);种子肿瘿线虫,粒线虫属(Anguina);茎叶线虫,滑刃线虫属(Aphelenchoides)如叶芽线虫(Aphelenchoidesbesseyi);刺线虫,长尾刺线虫(Belonolaimus longicaudatus)和其它针刺线虫属(Belonolaimus);松线虫,松材线虫(Bursaphelenchus lignicolus Mamiya etKiyohara)、松材线虫(Bursaphelenchus xylophilus)和其他伞滑刃线虫属(Bursaphelenchus);环形线虫,环纹线虫属(Criconema)、小环线虫属(Criconemella)、轮线虫属(Criconemoides)和中环线虫属(Mesocriconema);球茎线虫,腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)和其他茎线虫属(Ditylenchus);锥线虫,锥线虫属(Dolichodorus);螺旋形线虫、Heliocotylenchusmulticinctus和其它Helicotylenchus属;鞘线虫和鞘形(sheathoid)线虫,鞘线虫属(Hemicycliophora)和Hemicriconemoides属;Hirshmanniella属;矛线虫(Lancenematodes)、Hoploaimus属;伪根结线虫,珍珠线虫属(Nacobbus);针线虫,Longidoruselongatus和其他长针线虫属(Longidorus);根腐线虫,Pratylenchus brachyurus、Pratylenchus neglectus、穿刺根腐线虫(Pratylenchus penetrans)、Pratylenchuscurvitatus、Pratylenchus goodeyi和其他根腐线虫属(Pratylenchus);穿孔线虫,香蕉穿孔线虫(Radopholus similis)和其他穿孔线虫属(Radopholus);肾形线虫,Rotylenchusrobustus、香蕉肾形线虫(Rotylenchus reniformis)和其他盘旋线虫属(Rotylenchus);Scutellonema属;残根线虫,Trichodorus primitivus和其他毛刺线虫属(Trichodorus)、拟毛刺属(Paratrichodorus);阻长线虫,Tylenchorhynchus claytoni、Tylenchorhynchusdubius和其它矮化线虫属(Tylenchorhynchus);柑桔线虫,垫刃线虫属(Tylenchulus)如柑桔半穿刺线虫(Tylenchulus semipenetrans);剑线虫,剑线虫属(Xiphinema);以及其他植物寄生线虫属。
可通过式(I)化合物防治的其它害虫物种的实例包括:双壳纲(bivalva)如Dreissena spp.;腹足纲(Gastropoda)如Arion spp.、双脐螺属(Biomphalaria spp.)、水泡螺属(Bulinus spp.)、Deroceras spp.、Galba spp.、椎实螺属(Lymnaea spp.)、钉螺属(Oncomelania spp.)、琥珀螺属(Succinea spp.);蠕虫纲(helminths),例如十二指肠钩口线虫(Ancylostoma duodenale)、锡兰钩虫(ancylostoma ceylanicum)、巴西钩线虫(Acylostoma braziliensis)、钩线虫属(Ancylostoma spp.)、似引蛔线虫(Ascarislubricoides)、蛔虫属(Ascaris spp.)、马来丝虫(Brugia malayi)、帝纹布鲁线虫(Brugia timori)、仰口线虫(Bunostomum spp.)、夏伯特线虫属(Chabertia spp.)、支睾属(Clonorchis spp.)、库珀线虫属(Cooperia spp.)、双腔属(Dicrocoelium spp.)、Dictyocaulus filaria、阔节裂头绦虫(Diphyllobothrium latum)、麦地那龙线虫(Dracunculus medinensis)、Echinococcus granulosus、Echinococcus multilocularis、蛲虫(Enterobius vermicularis)、Faciola spp.、捻转血属(Haemonchus spp.),例如捻转血矛线虫(Haemonchus contortus.);鸡异刺线虫属(Heterakis spp.)、微小膜壳绦虫(Hymenolepis nana)、Hyostrongulus spp.、Loa Loa、细颈属(Nematodirus spp.)、食道口线虫属(Oesophagostomum spp.)、Opisthorchis spp.、旋盘尾丝虫(Onchocercavolvulus)、胃线虫属(Ostertagia spp.)、并殖属(Paragonimus spp.)、Schistosomenspp.、富氏类圆线虫(Strongyloides fuelleborni)、粪类圆线虫(Strongyloidesstercoralis)、类圆线虫属(Stronyloides spp.)、Taenia saginata、Taenia solium、旋毛虫(Trichinella spiralis)、乡土旋毛虫(Trichinella nativa)、Trichinella britovi、纳氏旋毛虫(Trichinella nelsoni)、Trichinella pseudopsiralis、毛形线虫属种(Trichostrongulus spp.)、Trichuris trichuria、班氏吴策线虫(Wuchereriabancrofti);等足目(Isopoda),例如Armadillidium vulgare、Oniscus asellus、Porcellio scaber;综合目(Symphyla),例如洁幺蚰(Scutigerella immaculata)。
可通过式(I)化合物防治的害虫物种的其它实例包括:奥国塞丽金龟(Anisopliaaustriaca)、Apamea spp.、棉小叶蝉(Austroasca viridigrisea)、稻蓟马(Baliothripsbiformis)、秀丽隐杆线虫(Caenorhabditis elegans)、Cephus spp.、芫菁龟象(Ceutorhynchus napi)、Chaetocnema aridula、台湾稻螟(Chilo auricilius)、Chiloindicus、Chilo polychrysus、Chortiocetes terminifera、Cnaphalocroci medinalis、Cnaphalocrosis spp.、苜蓿黄蝶(Colias eurytheme)、Collops spp.、Cornitermescumulans、翻枣蝽(Creontiades spp.)、圆头犀金龟属(Cyclocephala spp.)、Dalbulusmaidis、Deraceras reticulatum、甘蔗蛀虫(Diatrea saccharalis)、Dichelopsfurcatus、水稻铁甲(Diclaispaarmigera)、蛴螬(Diloboderus spp.),例如阿根廷兜(Diloboderus abderus);Edessa spp.、油松小卷蛾(Epinotia spp.)、蚁科(Formicidae)、大眼长蝽Geocoris spp.)、黄球白蚁(Globitermes sulfureus)、蝼蛄科(Gryllotalpidae)、红腿地螨(Halotydeus destructor)、Hipnodes bicolor、菲岛毛眼水蝇(Hydrellia philippina)、Julus spp.、Laodelphax spp.、Leptocorsia acuta、Leptocorsia oratorius、Liogenys fuscus、绿蝇属(Lucillia spp.)、Lyogenys fuscus、Mahanarva spp.、鳃金龟(Maladera matrida)、刷须野螟属(Marasmia spp.)、Mastotermesspp.、粉蚧(Mealybugs)、Megascelis ssp、Metamasius hemipterus、Microtheca spp.、魔鱼(Mocis latipes)、Murgantia spp.、Mythemina separata、Neocapritermes opacus、Neocapritermes parvus、Neomegalotomus spp.、新白蚁属(Neotermes spp.)、稻三点螟(Nymphula depunctalis)、Oebalus pugnax、Orseolia spp.,例如稻瘿蚊(Orseoliaoryzae);棉籽长蝽(Oxycarenus hyalinipennis)、Plusia spp.、福寿螺(Pomaceacanaliculata)、前角白蚁属(Procornitermes ssp)、Procornitermes triacifer、Psylloides spp.、Rachiplusia spp.、Rhodopholus spp.、Scaptocoris castanea、Scaptocoris spp.、三化螟属(Scirpophaga spp.),例如Scirpophaga incertulas、Scirpophaga innotata;拟稻黑蝽属(Scotinophara spp.),例如Scotinopharacoarctata;蛀茎夜蛾属(Sesamia spp.),例如大螟(Sesamia inferens)、Sogaellafrucifera、Solenapsis geminata、三刺角蝉属(Spissistilus spp.)、Stalk borer、稻蓟马(Stenchaetothrips biformis)、Steneotarsonemus spinki、棉卷叶野螟(Syleptaderogata)、Telehin licus、毛圆线虫属(Trichostrongylus spp.)。
配制剂
本发明还涉及包含辅助剂和至少一种本发明化合物I的农用化学组合物。
农用化学组合物包含杀虫有效量的化合物I。术语“有效量”表示组合物或化合物I在栽培植物、植物繁殖材料或作物上足以防治有害害虫或者在材料的保护中足以防治有害害虫且不产生对被处理植物的实质性损害的量。该量可在宽范围内变化且取决于各种因素,例如待防治的害虫种类、处理的栽培植物或材料、气候条件和所用具体化合物I。
化合物I、其N-氧化物和盐可转化成常规类型的农用化学组合物,例如溶液、乳液、悬浮液、粉剂、粉末、糊、颗粒、压片、胶囊及其混合物。组合物类型的实例为悬浮液(例如SC、OD、FS)、可乳化浓缩物(例如EC)、乳液(例如EW、EO、ES、ME)、胶囊(例如CS、ZC)、糊、锭剂、可润湿粉末或粉剂(例如WP、SP、WS、DP、DS)、压片(例如BR、TB、DT)、颗粒(例如WG、SG、GR、FG、GG、MG)、杀虫制品(例如LN以及用于植物繁殖材料如种子处理的凝胶配制剂(例如GF)。这些和其它组合物类型定义于“Catalogue of pesticide formulation types andinternational coding system”,Technical Monograph No.2,第6版,2008年5月,CropLife International中。
组合物以已知的方式制备,例如Mollet和Grubemann,Formulation technology,Wiley VCH,Weinheim,2001;或Knowles,New developments in crop protection productformulation,Agrow Reports DS243,T&F Informa,London,2005所述。
合适辅助剂的实例为溶剂、液体载体、固体载体或填料、表面活性剂、分散剂、乳化剂、润湿剂、助剂、增溶剂、渗透增强剂、保护胶体、粘着剂、增稠剂、湿润剂、驱避剂、引诱剂、取食刺激剂、相容剂、杀菌剂、防冻剂、消泡剂、着色剂、增粘剂和粘合剂。
合适的溶剂和液体载体为水和有机溶剂,例如中至高沸点的矿物油馏分如煤油、柴油;植物或动物来源的油;脂族、环状和芳族烃如甲苯、石蜡、四氢化萘、烷基化萘;醇,例如乙醇、丙醇、丁醇、苄醇、环己醇;二醇;DMSO;酮,例如环己酮;酯,例如乳酸酯、碳酸酯、脂肪酸酯、γ-丁内酯;脂肪酸;膦酸酯;胺;酰胺,例如N-甲基吡咯烷酮、脂肪酸二甲基酰胺;及其混合物。
合适的固体载体或填料为矿土,例如硅酸盐、硅胶、滑石、高岭土、石灰石、石灰、白垩、粘土、白云石、硅藻土、膨润土、硫酸钙、硫酸镁、氧化镁;多糖粉末,例如纤维素、淀粉;肥料,例如硫酸铵、磷酸铵、硝酸铵、尿素;植物来源的产品,例如谷物粉、树皮粉、木粉、坚果壳粉及其混合物。
合适的表面活性剂为表面活性化合物,例如阴离子、阳离子、非离子和两性表面活性剂、嵌段聚合物、聚电解质及其混合物。这类表面活性剂可用作乳化剂、分散剂、增溶剂、润湿剂、渗透增强剂、保护胶体或助剂。表面活性剂的实例列于McCutcheon’s,第1卷:Emulsifiers&Detergents,McCutcheon’s Directories,Glen Rock,美国,2008(国际版或北美版)中。
合适的阴离子表面活性剂为磺酸、硫酸、磷酸、羧酸的碱金属、碱土金属或铵盐及其混合物。磺酸盐的实例为烷基芳基磺酸盐、二苯基磺酸盐、α-烯烃磺酸盐、木素磺酸盐、脂肪酸和油的磺酸盐、乙氧基化烷基苯酚的磺酸盐、烷氧基化芳基苯酚的磺酸盐、缩合萘的磺酸盐、十二烷基-和十三烷基苯的磺酸盐、萘和烷基萘的磺酸盐、磺基琥珀酸盐或磺基琥珀酰胺酸盐。硫酸盐的实例为脂肪酸和油的硫酸盐、乙氧基化烷基苯酚的硫酸盐、醇的的硫酸盐、乙氧基化醇的硫酸盐或脂肪酸酯的硫酸盐。磷酸盐的实例为磷酸酯。羧酸盐的实例为烷基羧酸盐和羧化醇或烷基苯酚乙氧基化物。
合适的非离子表面活性剂为烷氧基化物、N-取代的脂肪酸酰胺、胺氧化物、酯、基于糖的表面活性剂、聚合物表面活性剂及其混合物。烷基化物的实例为以1-50当量烷氧基化的化合物,例如醇、烷基苯酚、胺、酰胺、芳基苯酚、脂肪酸或脂肪酸酯。氧化乙烯和/或氧化丙烯可用于烷氧基化,优选氧化乙烯。N-取代脂肪酸酰胺的实例为脂肪酸葡糖酰胺或脂肪酸链烷醇酰胺。酯的实例为脂肪酸酯、甘油酯或单酸甘油酯。基于糖的表面活性剂的实例为脱水山梨糖醇、乙氧基化脱水山梨糖醇、蔗糖和蔗糖酯或烷基聚葡糖苷。聚合物表面活性剂的实例为乙烯基吡咯烷酮、乙烯基醇或乙酸乙烯酯的均聚物或共聚物。
合适的阳离子表面活性剂为季铵表面活性剂,例如具有1或2个疏水基团的季铵化合物,或长链伯胺的盐。合适的两性表面活性剂为烷基甜菜碱和咪唑啉。合适的嵌段聚合物为包含聚氧化乙烯和聚氧化丙烯嵌段的A-B或A-B-A型,或包含链烷醇、聚氧化乙烯和聚氧化丙烯的A-B-C型嵌段聚合物。合适的聚电解质为聚酸或聚碱。聚酸的实例为聚丙烯酸的碱金属盐或聚酸梳型聚合物。聚碱的实例为聚乙烯基胺或聚乙烯胺。
合适助剂为本身具有可忽略的农药活性或甚至不具有农药活性的化合物,其改进化合物I对目标的生物性能。实例为表面活性剂、矿物或植物油和其它辅助剂。其它实例由Knowles,Adjuvants and Additives,Agrow Reports DS256,T&F Informa UK,2006,第5章列出。
合适的增稠剂为多糖(例如黄原胶、羧甲基纤维素)、有机粘土(有机改性或未改性的)、聚羧酸酯和硅酸盐。
合适的杀菌剂为溴硝丙二醇(bronopol)和异噻唑啉酮衍生物,例如烷基异噻唑啉酮和苯并异噻唑啉酮。
合适的防冻剂为乙二醇、丙二醇、脲和甘油。
合适的消泡剂为聚硅氧烷、长链醇和脂肪酸的盐。
合适的着色剂(例如红色、蓝色或绿色)为具有低水溶度的颜料和水溶性的染料。实例为无机着色剂(例如氧化铁、氧化钛、亚铁氰化铁)和有机着色剂(例如茜素-、偶氮-和酞菁着色剂)。
合适的增粘剂或粘合剂为聚乙烯吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇、聚丙烯酸酯、生物或合成蜡和纤维素醚。
组合物类型及其制备的实例为:
i)水溶性浓缩物(SL、LS)
将10-60重量%本发明化合物I和5-15重量%润湿剂(例如醇烷氧基化物)溶于水和/或水溶性溶剂(例如醇)中直至100重量%。活性物质经水稀释而溶解。
ii)分散性浓缩物(DC)
将5-25重量%本发明化合物I和1-10重量%分散剂(例如聚乙烯吡咯烷酮)溶于补至100重量%的有机溶剂(例如环己酮)中。用水稀释得到分散体。
iii)可乳化浓缩物(EC)
将15-70重量%本发明化合物I和5-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于补至100重量%的水不溶性有机溶剂(例如芳族烃)中。用水稀释得到乳液。
iv)乳液(EW、EO、ES)
将5-40重量%本发明化合物I和1-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于20-40重量%水不溶性有机溶剂(例如芳族烃)中。将该混合物借助乳化机器引入补至100重量%的水中,并制成均匀乳液。用水稀释得到乳液。
v)悬浮液(SC、OD、FS)
在搅拌球磨机中,将20-60重量%本发明化合物I通过加入2-10重量%分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)、0.1-2重量%增稠剂(例如黄原胶)和补至100重量%的水而粉碎得到细活性物质悬浮液。用水稀释得到活性物质的稳定悬浮液。对于FS型组合物,加入至多40重量%粘合剂(例如聚乙烯醇)。
vi)水分散性颗粒和水溶性颗粒(WG、SG)
将50-80重量%本发明化合物I通过加入补至100重量%的分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)而精细磨碎并通过工业装置(例如挤出机、喷雾塔、流化床)而制得水分散性或水溶性颗粒。用水稀释得到活性物质的稳定分散体或溶液。
vii)水分散性粉末和水溶性粉末(WP、SP、WS)
将50-80重量%本发明化合物I在转子-定子磨机中通过加入1-5重量%分散剂(例如木素磺酸钠)、1-3重量%润湿剂(例如醇乙氧基化物)和补至100重量%的固体载体如硅胶而磨碎。用水稀释得到活性物质的稳定分散体或溶液。
viii)凝胶(GW、GF)
在搅拌球磨机中,将5-25重量%本发明化合物I通过加入3-10重量%分散剂(例如木素磺酸钠)、1-5重量%增稠剂(例如羧甲基纤维素)和补至100重量%的水而粉碎以得到活性物质精细悬浮液。用水稀释得到活性物质的稳定悬浮液。
ix)微乳液(ME)
将5-20重量%本发明化合物I加入5-30重量%有机溶剂混合物(例如脂肪酸二甲基酰胺和环己酮)、10-25重量%表面活性剂混合物(例如醇乙氧基化物和芳基苯酚乙氧基化物)和补至100%的水中。将该混合物搅拌1小时以自发地产生热动力稳定微乳液。
x)微胶囊(CS)
将包含5-50重量%本发明化合物I、0-40重量%水不溶性有机溶剂(例如芳族烃)、2-15重量%丙烯酸单体(例如甲基丙烯酸甲酯、甲基丙烯酸和二-或三丙烯酸酯)的油相分散于保护胶体(例如聚乙烯醇)的水溶液中。通过自由基引发剂引发的自由基聚合导致聚(甲基)丙烯酸酯微胶囊的形成。或者,将包含5-50重量%本发明化合物I、0-40重量%水不溶性有机溶剂(例如芳族烃)和异氰酸酯单体(例如二苯基甲烷-4,4’-二异氰酸酯)的油相分散于保护胶体(例如聚乙烯醇)的水溶液中。多胺(例如六亚甲基二胺)的加入导致聚脲微胶囊的形成。单体合计为1-10重量%。重量%涉及总CS组合物。xi)可撒粉粉末(DP、DS)
将1-10重量%本发明化合物I细碎研磨并与补至100重量%的固体载体如细碎高岭土充分混合。
xii)颗粒(GR、FG)
将0.5-30重量%本发明化合物I细碎研磨并结合补至100重量%的固体载体(例如硅酸盐)。制粒通过挤出、喷雾干燥或流化床实现。
xiii)超低容量液体(UL)
将1-50重量%本发明化合物I溶于补至100重量%的有机溶剂如芳族烃中。
组合物类型i)至xiii)可任选包含其它辅助剂,例如0.1-1重量%杀菌剂、5-15重量%防冻剂、0.1-1重量%消泡剂和0.1-1重量%着色剂。
所得农用化学组合物通常包含0.01-95%,优选0.1-90%,最优选0.5-75重量%活性物质。活性物质以90-100%,优选95-100%的纯度(根据NMR谱)使用。
水溶性浓缩物(LS)、悬浮乳液(SE)、可流动浓缩物(FS)、干处理用粉末(DS)、淤浆处理用水分散性粉末(WS)、水溶性粉末(SS)、乳液(ES)、可乳化浓缩物(EC)和凝胶(GF)通常用于处理植物繁殖材料,特别是种子。所述组合物在2-10倍稀释以后得到即用制剂中0.01-60重量%,优选0.1-40重量%的活性物质浓度。施用可在播种以前或期间进行。将化合物I及其组合物施用或处理到植物繁殖材料,尤其是种子上的方法分别包括繁殖材料的拌种、涂覆、造粒、撒粉、浸泡和犁沟施用方法。优选,化合物I或其组合物分别通过使得不引起发芽的方法如拌种、遣粒、涂覆和撒粉施用于植物繁殖材料上。
当用于植物保护中时,施用的活性物质的量取决于所需效果的种类为0.001-2kg/ha,优选0.005-2kg/ha,更优选0.05-0.9kg/ha,特别是0.1-0.75kg/ha。
在植物繁殖材料如种子的处理中,例如对种子撒粉、涂覆或拌种中,通常想要0.1-1000g,优选1-1000g,更优选1-100g,最优选5-100g每100kg植物繁殖材料(优选种子)的活性物质量。
当用于保护材料或储存产品种时,施用的活性物质的量取决于施用面积的种类和所需效果。材料保护中常规施用的量为0.001g至2kg,优选0.005g至1kg活性物质每立方米处理材料。
可将各类油、润湿剂、助剂、肥料或微量营养素和其它农药(例如除草剂、杀虫剂、杀真菌剂、生长调节剂、安全剂)加入活性物质或包含它们的组合物中作为预混料,或者如果合适的话恰在紧邻使用前加入(桶混合)。这些试剂可与本发明组合物以1∶100-100∶1,优选1∶10-10∶1的重量比混合。
使用者通常由预剂量装置、背负式喷雾器、喷雾罐、喷雾飞机或灌溉系统施用本发明组合物。通常,农用化学组合物由水、缓冲剂和/或其它辅助剂补充至所需施用浓度,因此得到本发明即用喷雾液或农用化学组合物。通常,每公顷农业有用面积施用20-2000升,优选50-400升即用喷雾液。
根据一个实施方案,使用者本人可将本发明组合物的各个组分如试剂盒的各部分或者二元或三元混合物的各部分在喷雾罐中混合并且如果合适的话可加入其它辅助剂。
在另一实施方案中,使用者可将本发明组合物的各个组分或部分预混合组分,例如包含化合物I和/或来自下文进一步描述的组的活性物质的组分在喷雾罐中混合并且如果合适的话可加入其它辅助剂和添加剂。
在另一实施方案中,本发明组合物的各个组分或部分预混合组分,例如包含化合物I和/或来自下文进一步描述的组的活性物质的组分可联合(例如在桶混合以后)或相继地施用。
如上所述,在本发明方法中,化合物I可与其它活性成分一起,例如作为与其它农药、杀虫剂、除草剂、肥料如硝酸铵、尿素、钾碱和过磷酸盐、植物毒素和植物生长调节剂、安全剂和杀线虫剂的混合物施用。
这些其它成分可顺序地或者与上述组合物组合使用,如果合适的话还仅恰在使用以前加入(桶混合)。例如,可将植物在用其它活性成分处理以前或以后用本发明组合物喷雾。
混合物
可与本发明化合物一起使用并且可产生潜在的协同增效作用的根据the Mode ofAction Classification of the Insecticide Resistance Action Committee(IRRAC)分组和编号的下列M农药意欲阐述可能的组合,但不施以任何限制:
M.1以下类别的乙酰胆碱酯酶(AChE)抑制剂:
M.1A氨基甲酸酯类,例如涕灭威(aldicarb)、棉铃威(alanycarb)、虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁叉威(butocarboxim)、氧丁叉威(butoxycarboxim)、甲萘威(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、苯虫威(ethiofencarb)、丁苯威(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)、甲氨叉威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、特氨叉威(thiofanox)、混杀威(trimethacarb)、二甲威(XMC)、灭杀威(xylylcarb)和唑蚜威(triazamate);或者
M.1B有机磷酸酯类,例如高灭磷(acephate)、唑啶磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、保棉磷(azinphosmethyl)、硫线磷(cadusafos)、壤虫氯磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲磷(chlormephos)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos)/DDVP、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、EPN、乙硫磷(ethion)、灭克磷(ethoprophos)、氨磺磷(famphur)、克线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑酮磷(fosthiazate)、庚虫磷(heptenophos)、imicyafos、丙胺磷(isofenphos)、O-(甲氧基氨基硫代磷酰)水杨酸异丙酯、异唑磷(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)、一六零五(parathion)、甲基对硫磷(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(Phosphamidon)、辛硫磷(phoxim)、甲基虫螨磷(pirimiphos-methyl)、丙溴磷(profenofos)、烯虫磷(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、打杀磷(pyridaphenthion)、喹磷(quinalphos)、硫特普(sulfotep)、嘧丙磷(tebupirimfos)、硫甲双磷(temephos)、特丁磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(trichlorfon)和蚜灭多(vamidothion);
M.2.GABA门控氯化物通道拮抗剂,例如:
M.2A环二烯有机氯化合物类,例如硫丹(endosulfan)或氯丹(chlordane);或者
M.2B fiproles(苯基吡唑类),例如乙虫清(ethiprole)、锐劲特(fipronil)、丁虫腈(flufiprole)、pyrafluprole和pyriprole;
M.3以下类别的钠通道调制剂:
M.3A合成除虫菊酯类,例如氟丙菊酯(acrinathrin)、丙烯菊酯(allethrin)、d-顺-反丙烯除虫菊(d-cis-trans allethrin)、反丙烯除虫菊(d-trans allethrin)、氟氯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、bioallethrin S-cylclopentenyl、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfiuthrin)、β-氟氯氰聚酯(beta-cyfluthrin)、(RS)氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、γ-氟氯氰聚酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、β-氯氰菊酯(beta-cypermethrin)、θ-氯氰菊酯(theta-cypermethrin)、ζ-氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯(cyphenothrin)、溴氰菊酯(deltamethrin)、烯炔菊酯(empenthrin)、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、杀灭菊酯(fenvalerate)、氟氰菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、氟胺氰菊酯(tau-fluvalinate)、卤醚菊酯(halfenprox)、heptafluthrin、咪炔菊酯(imiprothrin)、氯氟醚菊酯(meperfluthrin)、甲氧苄氟菊酯(metofluthrin)、momfluorothrin、氯菊酯(permethrin)、苯醚菊酯(phenothrin)、炔酮菊酯(prallethrin)、丙氟菊酯(profluthrin)、除虫菊酯(pyrethrin)(pyrethrum)、灭虫菊(resmethrin)、灭虫硅醚(silafluofen)、七氟菊酯(tefluthrin)、四氟醚菊酯(tetramethylfluthrin)、胺菊酯(tetramethrin)、四溴菊酯(tralomethrin)和四氟菊酯(transfluthrin);或者
M.3B钠通道调制剂,例如DDT或甲氧滴滴涕(methoxychlor);
M.4以下类别的烟碱型乙酰胆碱受体激动剂(nAChR):
M.4A新烟碱类,例如啶虫脒(acetamiprid)、噻虫胺(chlothianidin)、cycloxaprid、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、硝胺烯啶(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam);或者如下化合物:
M.4A.2:(2E-)-1-[(6-氯吡啶-3-基)甲基]-N′-硝基-2-亚戊基肼羧酰亚胺酰胺;或
M4.A.3:1-[(6-氯吡啶-3-基)甲基]-7-甲基-8-硝基-5-丙氧基-1,2,3,5,6,7-六氢咪唑并[1,2-a]吡啶;
M.4B烟碱;
M.5赐诺司类(spinosyns)烟碱型乙酰胆碱受体变构激活体,例如艾克敌105(spinosad)或spinetoram;
M.6阿维菌素(avermectins)和米尔贝霉素(milbemycins)类的氯化物通道活化剂,例如齐墩螨素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、伊维菌素(ivermectin)、雷皮菌素(lepimectin)或弥拜菌素(milbemectin);
M.7拟保幼激素(Juvenile hormone mimics),例如:
M.7A保幼激素类似物如蒙五一二(hydroprene)、蒙七七七(kinoprene)和蒙五一五(methoprene);或者其它如M.7B双氧威(fenoxycarb)或M.7C蚊蝇醚(pyriproxyfen);
M.8其他非特异性(多位点)抑制剂,例如:
M.8A烷基卤代物如甲基溴和其它烷基卤代物,或者
M.8B氯化苦(chloropicrin),或者M.8C硫酰氟(sulfuryl fluoride),或者M.8D硼砂,或者M.8E吐酒石(tartar emetic);
M.9选择性同翅目昆虫取食阻滞剂,例如:
M.9B拒嗪酮(pymetrozine),或者M.9C氟啶虫酰胺(flonicamid);
M.10螨生长抑制剂,例如:
M.10A四螨嗪(clofentezine)、噻螨酮(hexythiazox)和氟螨嗪(diflovidazin),或者M.10B特苯唑(etoxazole);
M.11昆虫中肠膜微生物破话剂,例如苏云金芽孢杆菌(bacillus thuringiensis)或球形芽孢杆菌(Bacillus sphaericus)以及它们产生的杀虫蛋白质如苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis subsp.israelensis)、球形芽孢杆菌(Bacillussphaericus)、苏云金芽孢杆菌鲇泽亚种(bacillus thuringiensis subsp.aizawai)、苏云金芽孢杆菌库斯塔克亚种(bacillus thuringiensis subsp.kurstaki)和苏云金芽孢杆菌拟步行甲亚种(bacillus thuringiensis subsp.tenebrionis),或者Bt作物蛋白质:Cry1Ab、Cry1Ac、Cry1Fa、Cry2Ab、mCry3A、Cry3Ab、Cry3Bb和Cry34/35Ab1;
M.12线粒体ATP合酶抑制剂,例如:
M.12A杀螨硫隆(diafenthiuron),或者
M.12B有机锡杀螨剂如唑环锡(azocyclotin)、三环锡(cyhexatin)或杀螨锡(fenbutatin oxide),或者M.12C克螨特(propargite),或者M.12D四氯杀螨砜(tetradifon);
M.13借助破坏质子梯度的氧化磷酰化解偶联剂,例如氟唑虫清(chlorfenapyr)、DNOC或氟虫胺(sulfluramid);
M.14烟碱型乙酰胆碱受体(nAChR)通道阻滞剂,例如沙蚕毒素类似物如杀虫磺(bensultap)、巴丹(cartap hydrochloride)、硫环杀(thiocyclam)或杀虫双(thiosultapsodium);
M.15几丁质生物合成抑制剂0型,例如苯甲酰脲类,例如双三氟虫脲(bistrifluron)、定虫隆(chlorfluazuron)、氟脲杀(diflubenzuron)、氟螨脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氟氟丙氧脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、伏虫隆(teflubenzuron)或杀虫隆(triflumuron);
M.16几丁质生物合成抑制剂1型,例如噻嗪酮(buprofezin);
M.17脱毛破坏剂,双翅类的,例如灭蝇胺(cyromazine);
M.18蜕皮激素受体激动剂如二酰肼类,例如甲氧苯酰肼(methoxyfenozide)、双苯酰肼(tebufenozide)、特丁苯酰肼(halofenozide)、呋喃虫酰肼(fufenozide)或环虫酰肼(chromafenozide);
M.19奥克巴胺受体激动剂,例如虫螨脒(amitraz);
M.20线粒体络合物III电子转移抑制剂,例如:
M.20A灭蚁腙(hydramethylnon),或者M.20B灭螨醌(acequinocyl),或者M.20C嘧螨酯(fluacrypyrim);
M.21线粒体络合物I电子转移抑制剂,例如
M.21A METI杀螨剂和杀虫剂如喹螨醚(fenazaquin)、fenpyroximate、嘧胺苯醚(pyrimidifen)、哒螨酮(pyridaben)、吡螨胺(tebufenpyrad)或唑虫酰胺(tolfenpyrad),或者M.21B鱼藤酮(rotenone);
M.22电压相关钠通道阻滞剂,例如
M.22A二唑虫(indoxacarb),或者M.22B氰氟虫腙(metaflumizone),或者M.22B.1:2-[2-(4-氰基苯基)-1-[3-(三氟甲基)苯基]亚乙基]-N-[4-(二氟甲氧基)苯基]-肼羧酰胺,或者M.22B.2:N-(3-氯-2-甲基苯基)-2-[(4-氯苯基)[4-[甲基(甲基磺酰基)氨基]苯基]亚甲基]-肼羧酰胺;
M.23乙酰CoA羧化酶抑制剂,例如特窗酸和Tetramic酸衍生物,例如螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)或螺虫乙酯(spirotetramat);
M.24线粒体络合物IV电子转移抑制剂,例如:
M.24A膦,例如磷化铝、磷化钙、膦或磷化锌,或者M.24B氰化物;
M.25线粒体络合物II电子转移抑制剂,例如β-酮腈衍生物类,例如cyenopyrafen或丁氟螨酯(cyflumetofen);
M.28二酰胺类的利阿诺定(Ryanodine)受体-调制剂,例如氟虫酰胺(flubendiamide)、氯虫酰胺(chlorantraniliprole)溴氰虫酰胺(cyantraniliprole)或者邻苯二甲酰亚胺化合物:
M.28.1:(R)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺,和
M.28.2:(S)-3-氯-N1-{2-甲基-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基}-N2-(1-甲基-2-甲基磺酰基乙基)邻苯二甲酰胺,或者化合物:
M.28.3:3-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-羧酰胺(推荐ISO名:cyclaniliprole),或者化合物:
M.28.4:甲基-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]-1,2-二甲肼羧酸酯;或者选自M.28.5a)至M.28.51)的化合物:
M.28.5a)N-[4,6-二氯-2-[(二乙基-λ-4-硫烷亚基)氨基甲酰基]-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5b)N-[4-氯-2-[(二乙基-λ-4-硫烷亚基)氨基甲酰基]-6-甲基-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5c)N-[4-氯-2-[(二-2-丙基-λ-4-硫烷亚基)氨基甲酰基]-6-甲基-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5d)N-[4,6-二氯-2-[(二-2-丙基-λ-4-硫烷亚基)氨基甲酰基]-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5e)N-[4,6-二氯-2-[(二乙基-λ-4-硫烷亚基)氨基甲酰基]-苯基]-2-(3-氯-2-吡啶基)-5-(二氟甲基)吡唑-3-羧酰胺;
M.28.5f)N-[4,6-二溴-2-[(二-2-丙基-λ-4-硫烷亚基)氨基甲酰基]-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5g)N-[4-氯-2-[(二-2-丙基-λ-4-硫烷亚基)氨基甲酰基]-6-氰基-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5h)N-[4,6-二溴-2-[(二乙基-λ-4-硫烷亚基)氨基甲酰基]-苯基]-2-(3-氯-2-吡啶基)-5-(三氟甲基)吡唑-3-羧酰胺;
M.28.5i)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-2-吡啶基)-1H-吡唑-5-羧酰胺;
M.28.5j)3-氯-1-(3-氯-2-吡啶基)-N-[2,4-二氯-6-[[(1-氰基-1-甲基乙基)氨基]羰基]苯基]-1H-吡唑-5-酸酰胺;
M.28.5k)3-溴-N-[2,4-二氯-6-(甲基氨基甲酰基)苯基]-1-(3,5-二氯-2-吡啶基)-1H-吡唑-5-羧酰胺;
M.28.51)N-[4-氯-2-[[(1,1-二甲基乙基)氨基]羰基]-6-甲基苯基]-1-(3-氯-2-吡啶基)-3-(氟甲氧基)-1H-吡唑-5-羧酰胺;
或者选自如下的化合物:
M.28.6:N-(2-氰基丙-2-基)-N-(2,4-二甲基苯基)-3-碘代苯-1,2-二羧酰胺;或
M.28.7:3-氯-N-(2-氰基丙-2-基)-N-(2,4-二甲基苯基)-苯-1,2-二羧酰胺;
M.28.8a)1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-3-[[5-(三氟甲基)-2H-四唑-2-基]甲基]-1H-吡唑-5-羧酰胺;或
M.28.8b)1-(3-氯-2-吡啶基)-N-[4-氰基-2-甲基-6-[(甲基氨基)羰基]苯基]-3-[[5-(三氟甲基)-1H-四唑-1-基]甲基]-1H-吡唑-5-羧酰胺;
M.UN.未知或不确定作用模式的杀虫活性化合物,例如afidopyropen、afoxolaner、艾扎丁(azadirachtin)、磺胺蜻酯(amidoflumet)、苯螨特(benzoximate)、联苯肼酯(bifenazate)、溴螨酯(bromopropylate)、灭螨猛(chinomethionat)、cryolite、开乐散(dicofol)、啼虫胺(flufenerim)、flometoquin、氟噻虫砜(fluensulfone)、氟吡菌酰胺(fluopyram)、flupyradifurone、fluralaner、恶虫酮(metoxadiazone)、增效醚(piperonyl butoxide)、pyflubumide、啶虫丙醚(pyridalyl)、pyrifluquinazon、氟啶虫胺腈(sulfoxaflor)、tioxazafen、triflumezopyrim或者化合物:
M.UN.3:11-(4-氯-2,6-二甲基苯基)-12-羟基-1,4-二氧杂-9-氮杂二螺[4.2.4.2]-十四碳-11-烯-10-酮,或者化合物:
M.UN.4:3-(4’-氟-2,4-二甲基联苯-3-基)-4-羟基-8-氧杂-1-氮杂螺[4.5]癸-3-烯-2-酮,或者化合物:
M.UN.5:1-[2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚硫酰基]苯基]-3-(三氟甲基)-1H-1,2,4-三唑-5-胺,或者基于强固芽胞杆菌(bacillus firmus)的活性物质(Votivo,I-1582);或者选自M.UN.6组的化合物,其中化合物选自M.UN.6a)至M.UN.6k):
M.UN.6a)(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2,2-三氟-乙酰胺;
M.UN.6b)(E/Z)-N-[1-[(6-氯-5-氟-3-吡啶基)甲基]-2-吡啶亚基]-2,2,2-三氟-乙酰胺;
M.UN.6c)(E/Z)-2,2,2-三氟-N-[1-[(6-氟-3-吡啶基)甲基]-2-吡啶亚基]乙酰胺;
M.UN.6d)(E/Z)-N-[1-[(6-溴-3-吡啶基)甲基]-2-吡啶亚基]-2,2,2-三氟-乙酰胺;
M.UN.6e)(E/Z)-N-[1-[1-(6-氯-3-吡啶基)乙基]-2-吡啶亚基]-2,2,2-三氟-乙酰胺;
M.UN.6f)(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2-二氟-乙酰胺;
M.UN.6g)(E/Z)-2-氯-N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2-二氟-乙酰胺;
M.UN.6h)(E/Z)-N-[1-[(2-氯嘧啶-5-基)甲基]-2-吡啶亚基]-2,2,2-三氟-乙酰胺;
M.UN.6i)(E/Z)-N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2,3,3,3-五氟-丙酰胺);
M.UN.6j)N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2,2-三氟-硫代乙酰胺,或者化合物:
M.UN.6k)N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2,2,2-三氟-N′-异丙基-乙脒
或者化合物:
M.UN.8:8-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-羧酰胺;或
M.UN.9:4-[5-(3,5-二氯苯基)-5-(三氟甲基)-4H-异唑-3-基]-2-甲基-N-(1-氧代硫杂环丁烷-3-基)苯甲酰胺;或
M.UN.10:5-[3-[2,6-二氯-4-(3,3-二氯烯丙氧基)苯氧基]丙氧基]-1H-吡唑;或者选自组M.UN.11的化合物,其中化合物选自M.UN.11a)至M.UN.11p):
M.UN.11.a)3-[苯甲酰(甲基)氨基]-N-[2-溴-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]-2-氟-苯甲酰胺;
M.UN.11.b)3-(苯甲酰甲基氨基)-N-[2-溴-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]-6-(三氟甲基)苯基]-2-氟-苯甲酰胺;
M.UN.11.c)3-(苯甲酰甲基氨基)-2-氟-N-[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]-苯甲酰胺;
M.UN.11.d)N-[3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]氨基]羰基]苯基]-N-甲基-苯甲酰胺;
M.UN.11.e)N-[3-[[[2-溴-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]氨基]羰基]-2-氟苯基]-4-氟-N-甲基-苯甲酰胺;
M.UN.11.f)4-氟-N-[2-氟-3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]氨基]羰基]苯基]-N-甲基-苯甲酰胺;
M.UN.11.g)3-氟-N-[2-氟-3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]氨基]羰基]苯基]-N-甲基-苯甲酰胺;
M.UN.11.h)2-氯-N-[3-[[[2-碘-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]-6-(三氟甲基)苯基]氨基]羰基]苯基]-3-吡啶羧酰胺;
M.UN.11.i)4-氰基-N-[2-氰基-5-[[2,6-二溴-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]氨基甲酰]苯基]-2-甲基-苯甲酰胺;
M.UN.11.j)4-氰基-3-[(4-氰基-2-甲基-苯甲酰)氨基]-N-[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]-2-氟-苯甲酰胺;
M.UN.11.k)N-[5-[[2-氯-6-氰基-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]氨基甲酰]-2-氰基-苯基]-4-氰基-2-甲基-苯甲酰胺;
M.UN.11.l)N-[5-[[2-溴-6-氯-4-[2,2,2-三氟-1-羟基-1-(三氟甲基)乙基]苯基]氨基甲酰]-2-氰基-苯基]-4-氰基-2-甲基-苯甲酰胺;
M.UN.11.m)N-[5-[[2-溴-6-氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]氨基甲酰]-2-氰基-苯基]-4-氰基-2-甲基-苯甲酰胺;
M.UN.11.n)4-氰基-N-[2-氰基-5-[[2,6-二氯-4-[1,2,2,3,3,3-六氟-1-(三氟甲基)丙基]苯基]氨基甲酰]苯基]-2-甲基-苯甲酰胺;
M.UN.11.o)4-氰基-N-[2-氰基-5-[[2,6-二氯-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]氨基甲酰]苯基]-2-甲基-苯甲酰胺;
M.UN.11.p)N-[5-[[2-溴-6-氯-4-[1,2,2,2-四氟-1-(三氟甲基)乙基]苯基]氨基甲酰]-2-氰基-苯基]-4-氰基-2-甲基-苯甲酰胺;
或选自组M.UN.12的化合物,其中化合物选自M.UN.12a)至M.UN.12m):
M.UN.12.a)2-(1,3-二烷-2-基)-6-[2-(3-吡啶基)-5-噻唑基]-吡啶;
M.UN.12.b)2-[6-[2-(5-氟-3-吡啶基)-5-噻唑基]-2-吡啶基]-嘧啶;
M.UN.12.c)2-[6-[2-(3-吡啶基)-5-噻唑基]-2-吡啶基]-嘧啶;
M.UN.12.d)N-甲基磺酰基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-羧酰胺
M.UN.12.e)N-甲基磺酰基-6-[2-(3-吡啶基)噻唑-5-基]吡啶-2-羧酰胺
M.UN.12.f)N-乙基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙酰胺
M.UN.12.g)N-甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙酰胺
M.UN.12.h)N,2-二甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙酰胺
M.UN.12.i)N-乙基-2-甲基-N-[4-甲基-2-(3-吡啶基)噻唑-5-基]-3-甲硫基-丙酰胺
M.UN.12.j)N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-乙基-2-甲基-3-甲硫基-丙酰胺
M.UN.12.k)N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N,2-二甲基-3-甲硫基-丙酰胺
M.UN.12.l)N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-甲基-3-甲硫基-丙酰胺
M.UN.12.m)N-[4-氯-2-(3-吡啶基)噻唑-5-基]-N-乙基-3-甲硫基-丙酰胺;或者化合物:
M.UN.13:2-(4-甲氧基亚氨基环己基)-2-(3,3,3-三氟丙基磺酰基)乙腈;
或者化合物:
M.UN.14a)1-[(6-氯-3-吡啶基)甲基]-1,2,3,5,6,7-六氢-5-甲氧基-7-甲基-8-硝基-咪唑并[1,2-a]吡啶;或
M.UN.14b)1-[(6-氯吡啶-3-基)甲基]-7-甲基-8-硝基-1,2,3,5,6,7-六氢咪唑并[1,2-a]吡啶-5醇;或者化合物:
M.UN.15:1-[(2-氯-1,3-噻唑-5-基)甲基]-3-(3,5-二氯苯基)-9-甲基-4-氧代-4H-吡啶并[1,2-a]嘧啶-1--2-醇化物。
上面列举的M组市售化合物可在The Pesticide Manual,第15版,C.D.S.Tomlin,British Crop Protection Council(2011)中找到,还有其他出版物。
新烟碱类cycloxaprid由WO20120/069266和WO2011/06946已知,有时也称为Guadipyr的新烟碱类化合物M.4A.2由WO2013/003977已知,新烟碱类化合物M.4A.3.(在中国以哌虫啶审批)由WO2010/069266已知。Metaflumizone类似物M.22B.1描述于CN10171577中,类似物M.22B.2描述于CN102126994中。邻苯二甲酰胺类M.28.1和M.28.2都由WO 2007/101540已知。邻氨基苯甲酰胺M.28.3描述于WO2005/077934中。酰肼化合物M.28.4描述于WO 2007/043677中。邻氨基苯甲酰胺M.28.5a)至M.28.5h)可如WO 2007/006670、WO2013/024009和WO2013/024010所述制备。邻氨基苯甲酰胺化合物M.28.5i)描述于WO2011/085575中,化合物M.28.5j)描述于WO2008/134969中,化合物M.28.5k)描述于US2011/046186中,化合物M.28.5l)描述于WO2012/034403中。二酰胺化合物M.28.6和M.28.7可在CN102613183中找到。邻氨基苯甲酰胺化合物M.28.8a)和M.28.8b)由WO2010/069502已知。
喹啉衍生物flometoquin显示于WO2006/013896中。氨基呋喃酮化合物flupyradifurone由WO 2007/115644已知。亚砜亚胺化合物sulfoxaflor由WO2007/149134已知。合成除虫菊酯组中的momfluorothrin由US6908945已知和heptafluthrin由WO10133098已知。二唑酮化合物恶虫酮(metoxadiazone)可在JP13/166707中找到。吡唑杀螨剂pyflubumide由WO2007/020986已知。异唑啉化合物描述于以下出版物中:fluralaner在WO2005/085216中,afoxolaner在WO2009/002809和WO2011/149749中,异唑啉化合物M.UN.9在WO2013/050317中。pyripyropene衍生物afidopyropen描述于WO2006/129714中。杀线虫剂tioxazafen公开于WO09023721中,杀线虫剂fluopyram公开于WO2008126922中。包含flupyram的杀线虫混合物公开于WO2010108616中。triflumezopyrim化合物描述于WO2012/092115中。
螺缩酮取代的环状酮烯醇衍生物M.UN.3由WO2006/089633已知,联苯基取代的螺环酮烯醇衍生物M.UN.4由WO2008/067911已知。三唑基苯基硫化物M.UN.5描述于WO2006/043635中,基于强固芽胞杆菌(bacillus firmus)的生物防治剂描述于WO2009/124707中。
M.UN.6下所列化合物M.UN.6a)至M.UN.6i)描述于WO2012/029672中,化合物M.UN.6j)和M.UN.6k)描述于WO2013129688中。杀线虫剂化合物M.UN.8描述于WO2013/055584中,啶虫丙醚(pyridalyl)类类似物M.UN.10描述于WO2010/060379中。羧酰胺化合物M.UN.11.a)至M.UN.11.h)可如WO 2010/018714所述制备,羧酰胺M.UN.11i)至M.UN.11.p)描述于WO2010/127926中。吡啶基噻唑M.UN.12.a)至M.UN.12.c)由WO2010/006713已知,M.UN.12.c)和M.UN.12.d)由WO2012000896已知,M.UN.12.f)至M.UN.12.m)由WO2010129497已知。丙二腈化合物M.UN.13描述于WO2009/005110中。化合物M.UN.14a)和M.UN.14b)由WO2007/101369已知。化合物M.UN.15可在WO13192035中找到。
在本发明另一实施方案中,式(I)化合物或其立体异构体、盐、互变异构体和N-氧化物也可与作为化合物II的杀真菌剂一起施用。
可与本发明化合物一起使用的下列F活性物质意欲阐述可能的组合,但不限制它们:
F.I)呼吸抑制剂
F.I-1)Qo位点上的络合物III抑制剂:
嗜球果伞素类(strobilurins):腈嘧菌酯(azoxystrobin)、甲香菌酯(coumethoxystrobin)、丁香菌酯(coumoxystrobin)、醚菌胺(dimoxystrobin)、烯肟菌酯(enestroburin)、氟嘧菌酯(fluoxastrobin)、亚胺菌(kresoxim-methyl)、叉氨苯酰胺(metominostrobin)、肟醚菌胺(orysastrobin)、啶氧菌酯(picoxystrobin)、唑菌胺酯(pyraclostrobin)、唑胺菌酯(pyrametostrobin)、唑菌酯(pyraoxystrobin)、吡菌苯威(pyribencarb)、氯啶菌酯(triclopyricarb/chlorodincarb)、肟菌酯(trifloxystrobin)、2-[2-(2,5-二甲基-苯氧基甲基)-苯基]-3-甲氧基-丙烯酸甲酯和2(2-(3-(2,6-二氯苯基)-1-甲基-烯丙亚基氨基氧基甲基)-苯基)-2-甲氧基亚氨基-N甲基-乙酰胺;
唑烷二酮类和咪唑啉酮类:唑酮菌(famoxadone)、咪唑菌酮(fenamidone);
F.I-2)络合物II抑制剂(例如羧酰胺类):
羧酰替苯胺:麦锈灵(benodanil)、苯并烯氟菌唑(benzovindiflupyr)、bixafen、啶酰菌胺(boscalid)、萎锈灵(carboxin)、呋菌胺(fenfuram)、fenhexamid、氟吡菌酰胺(fluopyram)、氟酰胺(flutolanil)、呋吡唑灵(furametpyr)、吡唑萘菌胺(isopyrazam)、isotianil、丙氧灭绣胺(mepronil),氧化萎锈灵(oxycarboxin)、氟唑菌苯胺(penflufen)、吡噻菌胺(penthiopyrad)、氟唑环菌胺(sedaxane)、叶枯酞(tecloftalam)、溴氟唑菌(thifluzamide)、tiadinil、2-氨基-4甲基-噻唑-5-羧酰替苯胺、N-(3′,4′,5′三氟联苯-2基)-3-二氟甲基-1-甲基-1H-吡唑-4羧酰胺(fluxapyroxad)、N-(4′-三氟甲硫基联苯-2-基)-3二氟甲基-1-甲基-1H吡唑-4-羧酰胺、N-(2-(1,3,3-三甲基-丁基)-苯基)-1,3-二甲基-5氟-1H-吡唑-4羧酰胺、3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(三氟甲基)-1-甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、1,3-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(三氟甲基)-1,5-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(二氟甲基)-1,5-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、1,3,5-三甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(三氟甲基)-1-甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、1,3-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(三氟甲基)-1,5-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、3-(二氟甲基)-1,5-二甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺、1,3,5-三甲基-N-(1,1,3-三甲基茚满-4-基)吡唑-4-羧酰胺;
F.I-3)Qi位点上的络合物III抑制剂:氰霜唑(cyazofamid)、吲唑磺菌胺(amisulbrom)、[(3S,6S,7R,8R)-8-苄基-3-[(3-乙酰氧基-4-甲氧基-吡啶-2-羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环戊烷-7-基]2-甲基丙酸酯、[(3S,6S,7R,8R)-8-苄基-3-[[3-(乙酰氧基甲氧基)-4-甲氧基-吡啶-2-羰基]氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环戊烷-7-基]2-甲基丙酸酯、[(3S,6S,7R,8R)-8-苄基-3-[(3-异丁氧基羰氧基-4-甲氧基-吡啶-2-羰基)氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环戊烷-7-基]2-甲基丙酸酯、[(3S,6S,7R,8R)-8-苄基-3-[[3-(1,3-苯并二氧杂环戊烯-5-基甲氧基)-4-甲氧基-吡啶-2-羰基]氨基]-6-甲基-4,9-二氧代-1,5-二氧杂环戊烷-7-基]2-甲基丙酸酯、(3S,6S,7R,8R)-3-[[(3-羟基-4-甲氧基-2-吡啶基)羰基]氨基]-6-甲基-4,9-二氧代-8-(苯基甲基)-1,5-二氧杂环戊烷-7-基2-甲基丙酸酯;
F.I-4)其它呼吸抑制剂(络合物I,解偶联剂):氟嘧菌胺(diflumetorim)、(5,8-二氟喹唑啉-4-基)-{2-[2-氟4-(4-三氟甲基吡啶-2-基氧基)-苯基]-乙基}-胺;tecnazen;唑嘧菌胺(ametoctradin);硅噻菌胺(silthiofam);硝基苯基衍生物:乐杀螨(binapacryl)、敌螨通(dinobuton)、敌螨普(dinocap)、氟啶胺(fluazinam);嘧菌腙(ferimzone)、nitrthal-isopropyl,
还包括有机金属化合物:三苯基锡盐,例如薯瘟锡(fentin-acetate)、三苯基锡氯(fentin chloride)或毒菌锡(fentin hydroxide);
F.II)甾醇生物合成抑制剂(SBI杀真菌剂)
F.II-1)C14脱甲基酶抑制剂(DMI杀真菌剂,例如三唑类、咪唑类)
三唑类:戊环唑(azaconazole)、双苯三唑醇(bitertanol)、糠菌唑(bromuconazole)、环唑醇(cyproconazole)、醚唑(difenoconazole)、烯唑醇(diniconazole)、烯唑醇(diniconazole-M)、氧唑菌(epoxiconazole)、腈苯唑(fenbuconazole)、喹唑菌酮(fluquinconazole)、氟硅唑(flusilazole)、粉唑醇(flutriafol)、己唑醇(hexaconazole)、酰胺唑(imibenconazole)、环戊唑醇(ipconazole)、环戊唑菌(metconazole)、腈菌唑(myclobutanil)、多效唑(paclobutrazole)、戊菌唑(penconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、硅氟唑(simeconazole)、戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、三唑酮(triadimefon)、唑菌醇(triadimenol)、戊叉唑菌(triticonazole)、烯效唑(uniconazole)、1-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)-氧杂环丙烷基甲基]-5-硫氰酸根合-1H-[1,2,4]三唑、2-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)-氧杂环丙烷基甲基]-2H-[1,2,4]三唑-3-硫醇;
咪唑类:烯菌灵(imazalil)、稻瘟酯(pefurazoate)、oxpoconazole、丙氯灵(prochloraz)、氟菌唑(triflumizol);
嘧啶类、吡啶类和哌嗪类:异嘧菌醇(fenarimol)、氟苯嘧啶醇(nuarimol)、啶斑肟(pyrifenox)、嗪氨灵(triforine)、1-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)-氧杂环丙烷基甲基]-5-硫氰酸根合-1H-[1,2,4]三唑、2-[rel-(2S;3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)-氧杂环丙烷基甲基]-2H-[1,2,4]三唑-3-硫醇;
F.II-2)Delta 14-还原酶抑制剂(胺类,例如吗啉类、哌啶类)
吗啉类:4-十二烷基-2,6-二甲基吗啉(aldimorph)、吗菌灵(dodemorph)、吗菌灵乙酸盐(dodemorph-acetate)、丁苯吗啉(fenpropimorph)、克啉菌(tridemorph);
哌啶类:苯锈啶(fenpropidin)、粉病灵(piperalin);
螺缩酮胺类:螺茂胺(spiroxamine);
F.II-3)3-酮还原酶抑制剂:羟基苯胺类:环酰菌胺(fenhexamid);
F.III)核酸合成抑制剂
F.III-1)RNA、DNA合成:
苯基酰胺类或酰基氨基酸杀真菌剂类:苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M)、精苯霜灵(kiralaxyl)、甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M)(精甲霜灵(mefenoxam))、甲呋酰胺(ofurace)、霜灵(oxadixyl);
异唑类和异噻唑酮类:土菌消(hymexazole)、异噻菌酮(octhilinonc);
F.III-2)DNA拓扑异构酶抑制剂:喹菌酮(oxolinic acid);
F.III-3)核苷酸代谢(例如腺苷脱氨酶)、羟基(2-氨基)-嘧啶:磺嘧菌灵(bupirimate);
F.IV)细胞分裂和或细胞骨架抑制剂
F.IV-1)微管蛋白抑制剂:苯并咪唑类和托布津(thiophanate)类:苯菌灵(benomyl)、多菌灵(carbendazim)、麦穗宁(fuberidazole)、涕必灵(thiabendazole)、甲基托布津(thiophanate-methyl);
三唑并嘧啶类: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;
F.IV-2)其它细胞分裂抑制剂:苯甲酰胺类和苯基乙酰胺类:乙霉威(diethofencarb)、噻唑菌胺(ethaboxam)、戊菌隆(pencycuron)、氟吡菌胺(Fluopicolide)、苯酰菌胺(zoxamide);
F.IV-3)肌动蛋白抑制剂:二苯甲酮类:苯菌酮(metrafenone)、pyriofenone;
F.V)氨基酸和蛋白质合成抑制剂
F.V-1)蛋氨酸合成抑制剂(苯胺基-嘧啶类):
苯胺基-嘧啶类:环丙嘧啶(cyprodinil)、嘧菌胺(mepanipyrim)、nitrapyrin、二甲嘧菌胺(pyrimethanil);
F.V-2)蛋白质合成抑制剂(苯胺基-嘧啶类):
抗生素:灭瘟素(blasticidin-S)、春雷素(kasugamycin)、春雷霉素盐酸盐水合物(kasugamycin hydrochloride-hydrate)、米多霉素(mildiomycin)、链霉素(streptomycin)、土霉素(oxytetracyclin)、多氧霉素(polyoxine)、井冈霉素(validamycin A);
F.VI)信号传导抑制剂
F.VI-1)MAP/组氨酸激酶抑制剂(例如苯胺基-嘧啶类):
二羧酰亚胺类:唑呋草(fluoroimid)、异丙定(iprodione)、杀菌利(procymidone)、烯菌酮(vinclozolin);
苯基吡咯类:拌种咯(fenpiclonil)、氟菌(fludioxonil);
F.VI-2)G蛋白抑制剂:喹啉类:喹氧灵(quinoxyfen);
F.VII)类脂和膜合成抑制剂
F.VII-1)磷脂生物合成抑制剂
有机磷化合物:克瘟散(edifenphos)、异稻瘟净(iprobenfos)、定菌磷(pyrazophos);
二硫戊环类:稻瘟灵(isoprothiolane);
F.VII-2)类脂过氧化作用:芳族烃类:氯硝胺(dicloran)、五氯硝基苯(quintozene)、四氯硝基苯(tecnazene)、甲基立枯磷(tolclofos-methyl)、联苯、地茂散(Chloroneb)、氯唑灵(etridiazole);
F.VII-3)羧酸酰胺类(CAA杀真菌剂)
肉桂酸或扁桃酸酰胺:烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、双炔酰菌胺(mandipropamid)、丁吡吗啉(Pyrimorph);
缬氨酰胺氨基甲酸酯类:苯噻菌胺(benthiavalicarb)、异丙菌胺(iprovalicarb)、吡菌苯威(pyribencarb)、valifenalate和N-(1-(1-(4-氰基-苯基)乙烷磺酰基)-丁-2-基)氨基甲酸-(4-氟苯基)酯;
F.VII-4)影响细胞膜渗透性的化合物和脂肪酸类:1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮,氨基甲酸酯类:百维灵(propamocarb)、百维灵盐酸盐(propamocarb-hydrochlorid);
F.VII-5)脂肪酸酰胺水解酶抑制剂:1-[4-[4-[5-(2,6-二氟苯基)-4,5-二氢-3-异唑基]-2-噻唑基]-1-哌啶基]-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮;
F.VIII)具有多点作用的抑制剂
F.VIII-1)无机活性物质:波尔多混合液(Bordeaux mixture)、乙酸铜、氢氧化铜、氯氧化铜、碱式硫酸铜、硫;
F.VIII-2)硫代-和二硫代氨基甲酸酯类:福美铁(ferbam)、代森锰锌(mancozeb)、代森锰(maneb)、威百亩(metam)、methasulphocarb、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)、代森锌(zineb)、福美锌(ziram);
F.VIII-3)有机氯化合物类(例如邻苯二甲酰胺、磺酰胺、氯腈):敌菌灵(anilazine)、百菌清(chlorothalonil)、敌菌丹(captafol)、克菌丹(captan)、灭菌丹(folpet)、抑菌灵(dichlofluanid)、菌霉净(dichlorophen)、flusulfamide、六氯苯、五氯酚及其盐、四氯苯酞(phthalide)、对甲抑菌灵(tolylfluanid)、N-(4-氯-2-硝基-苯基)-N-乙基-4-甲基-苯磺酰胺;
F.VIII-4)胍类和其它:胍、多果定(dodine)、多果定游离碱、双胍盐(guazatine)、双胍醋酸盐(guazatine-acetate)、双胍辛醋酸盐(iminoctadine)、双胍辛醋酸盐(iminoctadine-triacetate)、双八胍盐(iminoctadine-tris(albesilate))、2,6-二甲基-1H,5H-[1,4]二硫(dithiino)[2,3-c:5,6-c′]二吡咯-1,3,5,7(2H,6H)-四酮;
F.VIII-5)蒽醌类:二噻农(dithianon);
F.IX)细胞壁合成抑制剂
F.IX-1)葡聚糖合成抑制剂:有效霉素(validamycin)、多氧霉素(polyoxin)B;
F.IX-2)黑色素合成抑制剂:咯喹酮(pyroquilon)、三环唑(tricyclazole)、氯环丙酰胺(carpropamid)、双氯氰菌胺(dicyclomet)、氰菌胺(fenoxanil);
F.X)植物防御诱导剂
F.X-1)水杨酸通道:噻二唑素(acibenzolar-S-methyl);
F.X-2)其它:噻菌灵(probenazole)、异噻菌胺(isotianil)、噻酰菌胺(tiadinil)、调环酸钙(prohexadione-calcium);膦酸盐类:藻菌磷(fosetyl)、藻菌磷(fosetyl-aluminum)、磷酸及其盐;
F.XI)未知作用模式:
溴硝丙二醇(bronopol)、灭螨猛(chinomethionat)、环氟菌胺(cyflufenamid)、清菌脲(cymoxanil)、棉隆(dazomet)、双乙氧咪菌威(debacarb)、哒菌清(diclomezine)、苯敌快(difenzoquat)、野燕枯甲基硫酸酯(difenzoquat-methylsulfate)、二苯胺(diphenylamin)、胺苯吡菌酮(fenpyrazamine)、氟联苯菌(flumetover)、磺菌胺(flusulfamide)、flutianil、磺菌威(methasulfocarb)、氯定(nitrapyrin)、异丙消(nitrothal-isopropyl)、oxathiapiprolin、喹啉铜(oxin-copper)、丙氧喹啉(proquinazid)、tebufloquin、叶枯酞(tecloftalam)、唑菌嗪(triazoxide)、2-丁氧基-6-碘-3-丙基苯并吡喃-4-酮、N-(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、N′-(4-(4-氯-3-三氟甲基-丙氧基)-2,5-二甲基-苯基)-N-乙基-N甲基甲脒、N′(4-(4-氟-3-三氟甲基-苯氧基)-2,5-二甲基-苯基)-N-乙基-N-甲基甲脒、N′-(2-甲基-5-三氟甲基-4-(3-三甲基硅烷基-丙氧基)-苯基)-N-乙基-N-甲基甲脒、N′-(5-二氟甲基-2甲基-4-(3-三甲基硅烷基-丙氧基)-苯基)-N-乙基-N-甲基甲脒、2-{1-[2-(5-甲基-3-三氟甲基-吡唑-1-基)-乙酰基]-哌啶-4-基}-噻唑-4-羧酸甲基-(1,2,3,4-四氢-萘-1-基)-酰胺、2-{1-[2-(5-甲基-3-三氟甲基-吡唑-1-基)-乙酰基]-哌啶-4-基}-噻唑-4-羧酸甲基-(R)-1,2,3,4-四氢-萘-1-基-酰胺、甲氧基-乙酸6-叔丁基-8-氟-2,3-二甲基-喹啉-4-基酯和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]-4-噻唑羧酰胺、3-[5-(4-氯-苯基)-2,3-二甲基-异唑烷-3基]-吡啶、pyrisoxazole、5-氨基-2-异丙基-3-氧代-4-邻-甲苯基-2,3-二氢-吡唑-1硫代碳酸S-烯丙基酯、N-(6-甲氧基-吡啶-3-基)环丙烷羧酸酰胺、5-氯-1(4,6-二甲氧基-嘧啶-2-基)-2-甲基-1H-苯并咪唑、2-(4-氯-苯基)-N-[4-(3,4-二甲氧基-苯基)-异唑-5-基]-2-丙-2-炔氧基-乙酰胺;
F.XI)生长调节剂:
脱落酸、呋喃丹(amidochlor)、嘧啶醇(ancymidol)、6-苄基氨基嘌呤、芸苔素内酯(brassinolide)、地乐胺(butralin)、矮壮素(chlormequat(chlormequat chloride))、氯化胆碱、环丙酸酰胺(cyclanilide)、丁酰肼(daminozide)、敌草克(dikegulac)、噻节因(dimethipin)、2,6-dimethylpuridine、乙烯利(ethephon)、氟节胺(flumetralin)、调嘧醇(flurprimidol)、达草氟(fluthiacet)、氯吡脲(forchlorfenuron)、赤霉酸、抗倒胺(inabenfide)、吲哚-3-乙酸、马来酰肼、氟草磺(mefluidide)、甲哌(mepiquat(mepiquat chloride))、萘乙酸、N-6-苄基腺嘌呤、多效唑(paclobutrazol)、调环酸钙(prohexadione(prohexadione-calcium))、prohydrojasmon、赛二唑素(thidiazuron)、抑芽唑(triapenthenol)、三硫代磷酸三丁酯、2,3,5三碘代苯甲酸、抗倒酯(trinexapac-ethyl)和烯效唑(uniconazole);
F.XII)生物防治剂
白粉寄生孢(Ampelomyces quisqualis)(例如来自Intrachem Bio GmbH&Co.KG,德国的AQ)、黄曲霉菌(Aspergillus flavus)(例如来自Syngenta,瑞士的)、出芽短梗霉菌(Aureobasidium pullulans)(例如来自bio-fermGmbH,德国的)、短小芽孢杆菌(Bacillus pumilus)(例如来自AgraQuestInc.,美国的和中的NRRL Accession No.B-30087)、枯草芽胞杆菌(Bacillus subtilis)(例如来自AgraQuest Inc.,美国的MAX和ASO中的分离物NRRL-Nr.B-21661)、解淀粉枯草芽孢杆菌变种(Bacillus subtilis var.Amyloliquefaciens FZB24(例如来自Novozyme Biologicals,Inc.,美国的)、假丝酵母(Candida oleophila)I-82(例如来自Ecogen Inc.,美国的)、假丝酵母(Candida saitoana)(例如来自Micro Flo Company,美国(BASF SE)和Arysta的(与溶菌酶的混合物)和)、脱乙酰壳多糖(例如来自BotriZen Ltd.,NZ的ARMOUR-ZEN)、Clonostachys rosea f.catenulata,也称为链孢粘帚菌(Gliocladium catenulatum)(例如分离物J1446:来自Verdera,芬兰的)、小盾壳霉(Coniothyrium minitans)(例如来自Prophyta,德国的)、板栗疫病菌(Cryphonectria parasitica)(例如来自CNICM,法国的Endothia parasitica)、白色隐球菌(Cryptococcus albidus)(例如来自Anchor Bio-Technologies,南非的YIELD)、大豆根腐病菌(Fusarium oxysporum)(例如来自S.I.A.P.A.,意大利的来自Natural Plant Protection,法国的)、Metschnikowia fructicola(例如来自Agrogreen,以色列的)、Microdochium dimerum(例如来自Agrauxine,法国的)、大伏革菌(Phlebiopsis gigantea)(例如来自Verdera,芬兰的)、Pseudozymaflocculosa(例如来自Plant Products Co.Ltd.,加拿大的)、寡雄腐霉(Pythium oligandrum)DV74(例如来自Remeslo SSRO,Biopreparaty,捷克共和国的)、Reynoutria sachlinensis(例如来自Marrone BioInnovations,美国的)、黄蓝状菌(Talaromyces flavus)V117b(例如来自Prophyta,德国的)、棘孢木霉(Trichoderma asperellum)SKT-1(例如来自Kumiai ChemicalIndustry Co.,Ltd.,日本的)、深绿木霉(T.atroviride)LC52(例如来自Agrimm Technologies Ltd,NZ的)、哈茨木霉(T.harzianum)T-22(例如来自Firma BioWorks Inc.,美国的)、哈茨木霉(T.harzianum)TH 35(例如来自Mycontrol Ltd.,以色列的)、哈茨木霉(T.harzianum)T-39(例如来自Mycontrol Ltd.,以色列和Makhteshim Ltd.,以色列的和)、哈茨木霉(T.harzianum)和绿色木霉菌(T.viride)(例如来自Agrimm Technologies Ltd,NZ的TRICHOPEL)、哈茨木霉(T.harzianum)ICC012和绿色木霉菌(T.viride)ICC080(例如来自Isagro Ricerca,意大利的WP)、多孢木霉(T.polysporum)和哈茨木霉(T.harzianum)(例如来自BINAB Bio-Innovation AB,瑞典的)、钩木霉(T.stromaticum)(例如来自C.E.P.L.A.C.,巴西的)、绿木霉(T.virens)GL-21(例如来自Certis LLC,美国的)、绿色木霉菌(T.viride)(例如来自Ecosense Labs.(India)Pvt.Ltd.,印度的来自T.Stanes&Co.Ltd.,印度的)、绿色木霉菌(T.viride)TV1(例如来自Agribiotec srl,意大利的绿色木霉菌(T.viride)TV1)、奥德曼细基格孢(Ulocladiumoudemansii)HRU3(例如来自Botry-Zen Ltd,NZ的)。
上列F组的市售化合物II可在The Pesticide Manual,第15版,C.D.S.Tomlin,British Crop Protection Council(2011)中找到,还可见于其他出版物。它们的制备及其对抗有害真菌的活性是已知的(参见:http://www.alanwood.net/pesticides/);这些物质是市售的。IUPAC描述的化合物、其制备及其杀真菌活性也是已知的(参见Can.J.PlantSci.48(6),587-94,1968;EP A 141 317;EP-A 152 031;EP-A 226 917;EP A 243 970;EPA 256 503;EP-A 428 941;EP-A 532 022;EP-A 1 028 125;EP-A 1 035 122;EP A 1 201648;EP A 1 122 244、JP 2002316902;DE 19650197;DE 10021412;DE 102005009458;US3,296,272;US 3,325,503;WO 98/46608;WO 99/14187;WO 99/24413;WO 99/27783;WO 00/29404;WO 00/46148;WO 00/65913;WO 01/54501;WO 01/56358;WO 02/22583;WO 02/40431;WO 03/10149;WO 03/11853;WO 03/14103;WO 03/16286;WO 03/53145;WO 03/61388;WO 03/66609;WO 03/74491;WO 04/49804;WO 04/83193;WO 05/120234;WO 05/123689;WO 05/123690;WO 05/63721;WO 05/87772;WO 05/87773;WO 06/15866;WO 06/87325;WO 06/87343;WO 07/82098;WO 07/90624、WO 11/028657)。
应用
动物害虫,例如昆虫、蜘蛛和线虫、植物、植物生长的土壤或水可通过本领域中已知的任何施用方法与本发明式I化合物或包含它们的组合物接触。因而,“接触”包括直接接触(将化合物/组合物直接施用于动物害虫或植物-通常植物的叶面、茎或根上)和间接接触(将化合物/组合物施用于动物害虫或植物的场所)。
式I化合物或包含它们的农药组合物可通过使植物/作物与杀虫有效量的式I化合物接触而用于保护生长的植物和作物以防动物害虫,尤其是昆虫、螨或蜘蛛侵袭或侵染。术语“作物”既指生长的作物,也指收获的作物。
本发明化合物和包含它们的组合物在防治各种栽培植物如禾谷类、根作物、油作物、蔬菜、香料、观赏植物,例如硬质小麦和其它小麦、大麦、燕麦、黑麦、玉米(饲料玉米和甜玉米/甜和田间玉米)、大豆、油作物、十字花科植物、棉花、向日葵、香蕉、稻、油菜籽油菜、芜菁油菜、糖用甜菜、饲料甜菜、茄子、土豆、禾草、草坪、草皮、饲料牧草、西红柿、韭菜、南瓜/西葫芦、卷心菜、卷心莴苣、胡椒、黄瓜、甜瓜、芸苔属、甜瓜、菜豆、豌豆、大蒜、洋葱、胡萝卜的种子、块茎植物如土豆、甘蔗、烟草、葡萄、矮牵牛花、老鹤草/鼠掌老鹤草、三色堇和凤仙花上的大量昆虫中特别重要。
本发明化合物通过用杀虫有效量的活性化合物处理昆虫或待保护以防昆虫侵袭的植物、植物繁殖材料如种子、土壤、表面、材料或空间,直接或以组合物的形式使用。施用可在植物、植物繁殖材料如种子、土壤、表面、材料或空间受昆虫侵染以前和以后进行。
本发明还包括对抗动物害虫的方法,其包括使动物害虫、其栖息地、繁殖地、食物源或动物害虫生长或可能生长的栽培植物、种子、土壤、区域、材料或环境,或待保护以防动物侵袭或侵染的材料、植物、种子、土壤、表面或空间与杀虫有效量的至少一种活性化合物I的混合物接触。
此外,动物害虫可通过将目标害虫、其食物源、栖息地、繁殖地或其场所与杀虫有效量的式I化合物接触而防治。因而,施用可在场所、生长的作物或收获的作物受害虫侵染以前或以后进行。
本发明化合物也可预防性地施用于预期害虫出现的地方。
式I化合物也可通过使植物与杀虫有效量的式I化合物接触用于保护生长的植物以防害虫侵袭或侵染。因而,“接触”包括直接接触(将化合物/组合物直接施用于害虫和/或植物-通常植物的叶面、茎或根上)和间接接触(将化合物/组合物施用于害虫和/或植物的场所)。
“场所”意指害虫或寄生虫生长或可能生长的栖息地、繁殖地、植物、种子、土壤、区域、材料或环境。
术语“植物繁殖材料”应当理解表示可用于植物繁殖的植物的所有有繁殖能力的部分,例如种子,和有生长力的植物材料如切条和块茎(例如土豆)。这包括植物的种子、根、果实、块茎、球根、根茎、芽、苗和其它部分。也可包括在发芽以后或在从土壤中出苗以后要移植的秧苗和幼小植物。这些植物繁殖材料可在种植或移植时或以前用植物保护化合物预防性处理。
术语“栽培植物”应当理解为包括已通过培育、突变或基因工程改性的植物。遗传修饰植物为遗传物质已通过使用DNA重组技术修饰而在自然环境下不易通过杂交育种、突变或自然重组得到的植物。通常,一个或多个基因已整合到遗传修饰植物的遗传物质中来改善植物的某些性能。这种遗传修饰还包括,但不限于蛋白质(寡肽或多肽)的靶向翻译后修饰,例如通过糖基化或聚合物添加如异戊二烯基化、乙酰化或法呢基化结构部分或PEG结构部分(例如如Biotechnol Prog.2001 Jul-Aug;17(4):720-8.,Protein Eng DesSel.2004 Jan;17(1):57-66,Nat Protoc.2007;2(5):1225-35.,Curr Opin ChemBiol.2006 Oct;10(5):487-91.Epub 2006Aug 28.,Biomaterials.2001 Mar;22(5):405-17,Bioconjug Chem.2005 Jan-Feb;16(1):113-21所公开的)。
术语“栽培植物”应当理解还包括由于常规育种方法或基因工程而被赋予了对特定类别的除草剂类的施用有耐性的植物,所述除草剂例如有:羟基-苯基丙酮酸双加氧酶(HPPD)抑制剂;乙酰乳酸合酶(ALS)抑制剂如磺酰基脲(例如见US 6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073)或咪唑啉酮(例如见US 6,222,100、WO 01/82685、WO 00/26390、WO 97/41218、WO 98/02526、WO 98/02527、WO 04/106529、WO 05/20673、WO 03/14357、WO 03/13225、WO 03/14356、WO 04/16073);烯醇丙酮酰莽草酸酯-3-磷酸酯合酶(EPSPS)抑制剂,如草甘膦(glyphosate)(例如见WO 92/00377);谷氨酰胺合成酶(GS)抑制剂如草铵膦(glufosinate)(例如见EP-A-0242236、EP-A-242246)或oxynil除草剂(例如见US 5,559,024)。数种栽培植物已通过常规育种方法(突变)被赋予了除草剂耐受性,例如耐受咪唑啉酮类如咪草啶酸(Imazamox)的夏季油菜(Canola)。基因工程方法已用于赋予栽培植物如大豆、棉花、玉米、甜菜和油菜对除草剂如草甘膦(glyphosate)和草铵膦(glufosinate)的耐受性,其中一些以商品名(草甘膦(glyphosate))和(草铵膦(glufosinate))市售。
术语“栽培植物”应当理解还包括这样的植物,它们通过使用DNA重组技术能合成一种或多种杀虫蛋白质,尤其是已知来自细菌属杆菌,特别是苏云金芽孢杆菌(Bacillusthuringiensis)的那些,例如δ-内毒素如CryIA(b)、CryIA(c)、CryIF、CryIF(a2)、CryIIA(b)、CryIIIA、CryIIIB(b1)或Cry9c;植物性杀虫蛋白质(VIP)如VIP1、VIP2、VIP3或VIP3A;细菌拓殖线虫的杀虫蛋白质如光杆菌属(Photorhabdus spp.)或异杆菌属(Xenorhabdusspp.);由动物产生的毒素如蝎毒素、蜘蛛毒素、黄蜂毒素,或其它昆虫特异性神经毒素;由真菌产生的毒素如链霉菌毒素,植物凝集素(lectins)如梨或大麦凝集素;凝集素(agglutinins);蛋白酶抑制剂如胰蛋白酶抑制剂、丝氨酸蛋白酶抑制剂、马铃薯块茎蛋白(patatin)、半胱氨酸蛋白酶抑制剂(cystatin)或木瓜酶抑制剂;核糖体钝化蛋白质(RIP)如蓖麻毒、玉米-RIP、相思豆毒蛋白、丝瓜籽蛋白(luffin)、肥皂草毒素(saporin)或异株泻根毒蛋白(bryodin);类固醇代谢酶如3-羟基类固醇氧化酶、蜕皮类固醇-IDP-糖基转移酶、胆固醇氧化酶、蜕皮激素抑制剂或HMG-CoA-还原酶;铁通道阻断剂如钠或钙通道阻断剂;保幼激素酯酶;利尿激素受体(helicokinin受体);1,2-二苯乙烯合酶、联苄合酶、几丁质酶或葡聚糖酶。在本发明上下文中,这些杀虫蛋白质或毒素应当明确理解为前毒素、杂化蛋白、截断或修饰蛋白质。杂化蛋白的特征在于蛋白质域的新组合(例如见WO 02/015701)。这些毒素或能合成这些毒素的遗传修饰植物例如公开于EP-A 374 753、WO 93/007278、WO 95/34656、EP-A 427 529、EP-A 451 878、WO 03/018810和WO 03/052073中。生产这类遗传修饰植物的方法通常为本领域技术人员已知的,并且例如公开于上述出版物中。含在遗传修饰植物中的这些杀虫蛋白质赋予产生这些蛋白质的植物防护某些分类学上节肢动物组的有害害虫,特别是甲虫(鞘翅目(Coleoptera))、飞虫(双翅目(Diptera))和蝴蝶和蛾(鳞翅目(Lepidoptera)),和植物寄生线虫(线虫类(Nematoda))。
术语“栽培植物”应当理解还包括这样的植物,它们通过使用DNA重组技术能够合成一种或多种蛋白质以提高那些植物对细菌、病毒或真菌病原体的抗性或耐受性。这种蛋白质的实例为所谓的“病原性相关蛋白质”(PR蛋白质,例如见EP-A 0 392 225)、植物抗病性基因(例如土豆栽培变种,其表达对来自于墨西哥野生土豆Solanum bulbocastanum)的致病疫霉(Phytophthora infestans)起作用的抗性基因,或T4-lyso-zym(土豆栽培变种,其例如能合成具有提高的对细菌如Erwinia amylvora的抗性的这些蛋白质)。生产这种遗传修饰植物的方法通常为本领域技术人员已知的,并且例如公开于上述出版物中。
术语“栽培植物”应当理解还包括这样的植物,它们通过使用DNA重组技术能够合成一种或多种蛋白质以提高那些植物的产量(例如生物质产量、谷粒收率、淀粉含量、油含量或蛋白质含量),耐干旱、盐或其它限制生长的环境因素或耐害虫和真菌、细菌或病毒病原体。
术语“栽培植物”应当理解还包括这样的植物,它们通过使用DNA重组技术而含有改进量的合意物质或含有合意新物质,尤其是改善人类或动物营养,例如产生促进健康的长链ω-3脂肪酸或不饱和ω-9脂肪酸的油作物(例如油菜)。
术语“栽培植物”应当理解还包括这样的植物,它们通过使用DNA重组技术而含有改进量的合意物质或含有合意新物质,尤其是改善原料生产,例如产生提高量的支链淀粉的土豆(例如土豆)。
一般而言,“杀虫有效量”意指实现对生长可观察到的效力,包括坏死、死亡、阻滞、防止和除去、破坏或减少目标有机体的出现和活性的效力所需的活性成分的量。对于本发明所用各种化合物/组合物,杀虫有效量可变化。组合物的杀虫有效量也可根据主导条件如所需的杀虫效力和持续时间、气候、目标物种、场所、施用模式等变化。
在土壤处理或施用于害虫居所或巢的情况下,活性成分的量为0.0001-500g每100m2,优选0.001-20g每100m2。
材料保护中的常规施用率为例如0.01g至1000g活性化合物每m2处理材料,理想地,0.1g至50g每m2。
用于浸渍材料的杀虫组合物通常包含0.001-95重量%,优选0.1-45重量%,更优选1-25重量%至少一种驱避剂和/或杀虫剂。
对于在处理作物植物中的使用,本发明活性成分的施用率可以为0.1g至4000g每公顷,理想地为25g至600g每公顷,更理想地为50g至500g每公顷。
式I化合物通过接触(经由土壤、玻璃、墙壁、床帐(bed net)、地毯、植物部分或动物部分)和摄食(诱饵或植物部分)而发挥效力。
还可施用本发明化合物以防非作物昆虫害虫如蚂蚁、白蚁、黄蜂、蝇、蚊、蟋蟀或蟑螂。对于用于对抗所述非作物害虫,式I化合物优选以诱饵制剂使用。
诱饵可以为液体、固体或半固体制剂(例如凝胶)。固体诱饵可成形为适于相应施用的各种形状和形式,例如颗粒、块、棒、片。液体诱饵可装入各种装置中以确保正确施用,例如开口容器、喷雾装置、液滴源或蒸发源。凝胶可基于水性或油性基质并且可根据与粘性、保水性或老化特性相关的特殊需要而配置。
组合物中所用的诱饵为对刺激昆虫如蚂蚁、白蚁、黄蜂、蝇、蚊、蟋蟀等或蟑螂来吃具有足够吸引力的产品。这种吸引力可通过使用取食刺激剂或性信息素来控制。取食刺激剂例如但不仅仅选自动物和/或植物蛋白质(肉粉、鱼粉或血粉,昆虫部分、蛋黄),动物和/或植物来源的脂肪和油,或单、寡-或聚有机糖类,尤其是蔗糖、乳糖、果糖、右旋糖、葡萄糖、淀粉、果胶或甚至糖蜜或蜂蜜。水果、作物、植物、动物、昆虫或其特殊部分的新鲜或腐烂部分也可用作取食刺激剂。已知性信息素更具昆虫特异性。特殊信息素描述于文献中并且为本领域技术人员已知的。
对于在诱饵组合物中的使用,活性成分的典型含量为0.001重量%至15重量%,理想地,0.001重量%至5%重量%活性化合物。
气溶胶(例如在喷雾罐中)、油喷雾或泵喷雾形式的式I化合物配制剂非常适于非专业使用者防治害虫如蝇、跳蚤、扁虱、蚊或蟑螂。气溶胶配方优选包含活性化合物,溶剂,例如低级醇(例如甲醇、乙醇、丙醇、丁醇)、酮(例如丙酮、甲乙酮)、沸程为约50-250℃的链烷烃(例如煤油)、二甲基甲酰胺、N-甲基吡咯烷酮、二甲亚砜、芳族烃如甲苯、二甲苯、水,此外还有辅助剂,例如乳化剂如山梨糖醇单油酸酯、具有3-7摩尔氧化乙烯的油基乙氧基化物、脂肪醇乙氧基化物,芳香油,例如香精油、中脂肪酸与低级醇的酯、芳族羰基化合物,如果合适的话稳定剂,例如苯甲酸钠、两性表面活性剂、低级环氧化物、原甲酸三乙酯,以及如果需要的话推进剂如丙烷、丁烷、氮气、压缩空气、二甲醚、二氧化碳、一氧化二氮或者这些气体的混合物。
油喷雾配制剂与气溶胶配方不同的是不使用推进剂。
对于喷雾组合物中的使用,活性成分的含量为0.001-80重量%,优选0.01-50重量%,最优选0.01-15重量%。
式I化合物及其相应的组合物也可用于蚊虫和蚊香(fumigating coils)、烟筒、蒸发板或长期蒸发器以及蛾纸、蛾垫或其它热独立性蒸发器体系中。
用式I化合物及其相应的组合物防治由昆虫传播的传染病(例如疟疾、登革热和黄热病、淋巴丝虫病和利什曼病)的方法还包括处理小屋和房子的表面,将窗帘、帐篷、衣物件、床帐空气喷雾和浸渍、采采蝇捕集器等。施用于纤维、织物、针织品、无纺布、网材料或箔和防水油布上的杀虫组合物优选包含含有杀虫剂、任选驱避剂和至少一种粘合剂的混合物。合适的驱避剂例如为N,N-二乙基-间-甲苯甲酰胺(DEET)、N,N-二乙基苯基乙酰胺(DEPA)、1-(3-环己-1-基-羰基)-2-甲基哌啶、(2-羟甲基环己基)乙酸内酯、2-乙基-1,3-己二醇、避蚊酮(indalone)、甲基辛癸酰胺(MNDA)、不用于昆虫防治的合成除虫菊酯类如{(+/-)-3-烯丙基-2-甲基-4-氧代环戊-2-(+)-烯基-(+)-反式-菊酸酯(S-反丙烯除虫菊(Esbiothrin))、衍生自植物提取物或者与植物提取物相同的驱避剂如柠檬烯、丁子香酚、(+)-Eucamalol(1)、(-)-1-表-eucamalol或来自植物如花皮桉(Eucalyptus maculata)、蔓荆(Vitex rotundifolia)、Cymbopogan martinii、香茅(Cymbopogan citratus)(香茅草)、亚香茅(Cymopogan nartdus)(香茅)的粗植物提取物。合适的粘合剂例如选自如下物质的聚合物和共聚物:脂族酸的乙烯酯(例如乙酸乙烯酯和vinyl versatate)、醇的丙烯酸和甲基丙烯酸酯如丙烯酸丁酯、丙烯酸2-乙基己酯和丙烯酸甲酯、单-和二-烯属不饱和烃如苯乙烯和脂族二烯如丁二烯。
窗帘和床帐的浸渍通常通过将织物材料浸入杀虫剂的乳液或分散体中或者将它们喷雾在帐上而进行。
式I化合物及其组合物可用于保护木制材料如树、木栅栏、枕木等和建筑物如房子、外屋、工厂,以及建筑材料、家具、皮革、纤维、乙烯基制品、电线和电缆等以防蚂蚁和/或白蚁,以及用于防治蚂蚁和白蚁不损害作物或人类(例如当害虫侵入房屋和公共建筑时)。式I化合物不仅施用于周围土壤表面或者地板下土壤以保护木制材料,而且它可施用于木材制品如地板下混凝土、凉亭柱、横梁、胶合板、家具等的表面,木制制品如颗粒板、半板等和乙烯基制品如涂覆电线、乙烯板,热绝缘材料如苯乙烯泡沫等。在施用以防蚂蚁损害作物或人类的情况下,将本发明的蚂蚁防治剂施用于作物或周围土壤,或者直接施用于蚂蚁的巢等。
种子处理
式I化合物还适于种子处理以保护种子以防昆虫害虫,特别是土壤生昆虫害虫,和保护产生的植物根和芽以防土壤害虫和叶面昆虫。
式I化合物特别可用于保护种子以防土壤害虫和保护产生的植物根和芽以防土壤害虫和叶面昆虫。优选保护产生的植物根和芽。更优选保护产生的植物芽以防刺吸式昆虫,其中最优选保护以防蚜虫。
因此,本发明包括保护种子以防昆虫,特别是土壤昆虫,和保护秧苗根和芽以防昆虫,特别是土壤和叶面昆虫的方法,所述方法包括在播种以前和/或催芽以后使种子与通式I化合物或其盐接触。特别优选的是保护植物根和芽的方法,更优选的是保护植物芽以防刺吸式昆虫的方法,最优选的是保护植物芽以防蚜虫的方法。
术语种子包括种子和所有种类的植物繁殖体,包括但不限于真正的种子、插条(seed pieces)、吸根、球茎、球根、果实、块茎、谷粒、切条、切枝等,在优选实施方案中意指真正的种子。
术语种子处理包括本领域已知的所有适合的种子处理技术,例如拌种、种子涂覆、种子撒粉、种子浸泡和种子造粒。
本发明还包含涂覆有或含有活性化合物的种子。
术语“涂覆有和/或含有”通常表示在施用时活性成分大部分位于繁殖产品表面上,但取决于施用方法,更多或更少部分成分可能渗入繁殖产品中。当(再)种植所述繁殖产品时,它可吸收活性成分。
适合的种子为禾谷类、根作物、油作物、蔬菜、香料、观赏植物的种子,例如硬质小麦和其它小麦、大麦、燕麦、黑麦、玉米(饲料玉米和糖玉米/甜玉米和田间玉米)、大豆、油作物、十字花科植物、棉花、向日葵、香蕉、稻、油籽油菜、芜菁油菜、糖用甜菜、饲料甜菜、茄子、马铃薯、草、草坪、草皮、饲料牧草、西红柿、韭菜、南瓜/西葫芦、甘蓝、卷心莴苣、胡椒、黄瓜、甜瓜、芸苔属、甜瓜、菜豆、豌豆、大蒜、洋葱、胡萝卜、块茎类植物如土豆、甘蔗、烟草、葡萄、矮牵牛花、老鹤草/鼠掌老鹤草、三色堇和凤仙花属植物的种子。
另外,活性化合物也可用于处理由于育种,包括遗传工程方法,可耐受除草剂或杀真菌剂或杀虫剂作用的植物的种子。
例如,活性化合物可用于处理耐选自磺酰脲、咪唑啉酮、草铵膦(glufosinate-ammonium)或草甘膦异丙铵(glyphosate-isopropyl ammonium)和类似活性物质的除草剂的植物的种子(例如见EP-A-0242236、EP-A-242246)(WO 92/00377)(EP-A-0257993、美国专利No.5,013,659),或用于能够产生使植物耐某些害虫的苏云金芽孢杆菌(Bacillusthuringiensis)毒素(Bt毒素)的转基因作物植物如棉花中(EP-A-0142924、EP-A-0193259)。
此外,活性化合物还可用于处理可例如通过传统育种方法和/或产生突变体,或通过重组程序而产生的与现有植物相比具有改进性能的植物的种子。例如已有很多将作物植物重组改性以使植物中合成的淀粉改性的情况(例如WO 92/11376、WO 92/14827、WO 91/19806),或具有改性脂肪酸组成的转基因作物植物的情况(WO 91/13972)。
活性化合物的种子处理施用在植物播种以前和植物出苗以前通过对种子喷雾或撒粉而进行。
尤其可用于种子处理的组合物为例如:
A 可溶性浓缩物(SL、LS)
D 乳液(EW、EO、ES)
E 悬浮液(SC、OD、FS)
F 水分散性颗粒和水溶性颗粒(WG、SG)
G 水分散性粉末和水溶性粉末(WP、SP、WS)
H 凝胶配制剂(GF)
I 可撒粉粉末(DP、DS)
常规种子处理配制剂包括例如可流动浓缩物FS、溶液LS、干处理用粉末DS、淤浆处理用水分散性粉末WS、水溶性粉末SS以及乳液ES和EC和凝胶配制剂GF。这些配制剂可稀释或未稀释而施用于种子。在种子上的施用在播种之前,或者直接在种子上或者在催芽之后进行。
在一个优选实施方案中,FS配制剂用于种子处理。FS配制剂通常可包含1-800g/l活性成分、1-200g/l表面活性剂、0-200g/l防冻剂、0-400g/l粘合剂、0-200g/l颜料和至多1升溶剂,优选水。
用于种子处理的式l化合物的尤其优选的FS配制剂通常包含0.1-80重量%(1-800g/l)活性成分,0.1-20重量%(1-200g/l)至少一种表面活性剂,例如0.05-5重量%润湿剂和0.5-15重量%分散剂,至多20重量%,例如5-20重量%防冻剂,0-15重量%,例如1-15重量%颜料和/或染料,0-40重量%,例如1-40重量%粘合剂(粘着剂/粘合剂),任选至多5重量%,例如0.1-5重量%增稠剂,任选0.1-2%消泡剂,和任选的防腐剂如杀生物剂、抗氧化剂等,其量例如为0.01-1重量%,以及直至100重量%的填料/赋形剂。
种子处理配制剂也可另外包含粘合剂和任选着色剂。
可加入粘合剂以改善处理以后活性材料在种子上的粘着力。合适的粘合剂为氧化烯如氧化乙烯或氧化丙烯的均聚物和共聚物、聚乙酸乙烯酯、聚乙烯醇、聚乙烯吡咯烷酮及其共聚物、乙烯-乙酸乙烯酯共聚物、丙烯酸均聚物和共聚物、聚乙烯胺、聚乙烯酰胺和聚乙烯亚胺、多糖如纤维素、甲基纤维素和淀粉、聚烯烃均聚物和共聚物如烯烃/马来酸酐共聚物、聚氨酯、聚酯、聚苯乙烯均聚物和共聚物。
任选地,着色剂也可包含在配制剂中。适于种子处理配制剂的着色剂或染料为Rhodamin B、C.I.颜料红(Pigment Red)112、C.I.溶剂红(Solvent Red)1、颜料蓝(pigmentblue)15:4、颜料蓝(pigment blue)15:3、颜料蓝(pigment blue)15:2、颜料蓝(pigmentblue)15:1、颜料蓝(pigment blue)80、颜料黄(pigment yellow)1、颜料黄(pigmentyellow)13、颜料红(pigment red)112、颜料红(pigment red)48:2、颜料红(pigment red)48:1、颜料红(pigment red)57:1、颜料红(pigment red)53:1、颜料橙(pigment orange)43、颜料橙(pigment orange)34、颜料橙(pigment orange)5、颜料绿(pigment green)36、颜料绿(pigment green)7、颜料白(pigment white)6、颜料棕(pigment brown)25、碱性紫(basic violet)10、碱性紫(basic violet)49、酸性红(acid red)51、酸性红(acid red)52、酸性红(acid red)14、酸性蓝(acid blue)9、酸性黄(acid yellow)23、碱性红(basicred)10、碱性红(basic red)108。
胶凝剂的实例为角叉菜
在种子处理中,化合物I的施用率通常为0.1g至10kg每100kg种子,优选1g至5kg每100kg种子,更优选1g至1000g每100kg种子,特别是1g至200g每100kg种子。
因此,本发明还涉及包含如本文所定义的式I化合物或I的农用盐的种子。化合物I或其农用盐的量通常在0.1g至10kg每100kg种子,优选1g至5kg每100kg种子,特别是1g至1000g每100kg种子的范围变化。对于具体作物如莴苣,施用率可以较高。
动物健康
式I化合物或其对映体或其兽用可接受盐还特别适用于对抗动物中和动物上的寄生虫。
因此,本发明的目的还在于提供防治动物中和动物上的寄生虫的新方法。本发明的另一个目的是提供对于动物更安全的农药。本发明的另一个目的进一步在于提供可以以比现有农药更低的剂量使用的动物杀虫剂。本发明的另一个目的是提供对寄生虫提供长期后效控制的动物杀虫剂。
本发明还涉及用于对抗动物中和动物上寄生虫的包含杀寄生虫有效量的式I化合物或其对映体或其兽用可接受盐和可接受载体的组合物。
本发明还提供处理、防治、防止和保护动物以防寄生虫侵袭和侵染的方法,其包括为动物口服、局部或肠道外给药或施用杀寄生虫有效量的式I化合物或其对映体或其兽用可接受盐或包含它的组合物。
本发明还提供制备用于处理、防治、防止或保护动物以防寄生虫侵袭或侵染且包含杀寄生虫有效量的式I化合物或其对映体或其兽用可接受盐或包含它的组合物的组合物的方法。
对抗农业害虫的化合物的活性不意味着它们适于防治动物中和动物上的体内-和体外寄生虫,这例如要求在口服施用情况下的低、非催吐剂量、与动物的代谢相容性、低毒性和安全操作。
令人惊讶的是,现在已发现式I化合物适于对抗动物中和动物上的体内-和体外寄生虫。
式I化合物或其对映体或其兽用可接受盐和包含它们的组合物优选用于防治和防止动物,包括温血动物(包括人类)和鱼不受侵染和侵袭。它们例如适于防治和防止哺乳动物如牛、绵羊、猪、骆驼、鹿、马、猪、家禽、兔、山羊、狗和猫、水牛、驴、扁角鹿和驯鹿,以及毛皮动物如貂、栗鼠和浣熊,鸟类如母鸡、鹅、火鸡和鸭以及鱼类如淡水鱼和咸水鱼如鲑鱼、鲤鱼和鳗鱼中的侵染和侵袭。
式I化合物或其对映体或其兽用可接受盐和包含它们的组合物优选用于防治和防止家养动物如狗和猫中的侵染和侵袭。
温血动物和鱼中的侵染包括但不限于虱子、羽虱、扁虱、鼻蝇、羊蜱蝇、刺蝇、muscoid蝇、蝇、myiasitic蝇幼虫、恙螨、蚋、蚊子和跳蚤。
式I化合物或其对映体或其兽用可接受盐和包含它们的组合物适于内吸和/或非内吸防治体外和/或体内寄生虫。它们对于所有或一些发育阶段具有活性。
式I化合物尤其可用于对抗体外寄生虫。
式I化合物尤其可用于对抗以下目和属的寄生虫:
跳蚤(蚤目(Siphonaptera)),例如猫跳蚤(Ctenocephalides felis)、狗跳蚤(Ctenocephalides canis)、印鼠客蚤(Xenopsylla cheopis)、致痒蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)和具带病蚤(Nosopsyilus fasciatus),
蟑螂(蜚蠊目(Blattaria-Blattodea)),例如德国小蠊(Blattella germanica)、Blattella asahinae、美洲蟑螂(Periplaneta americana)、日本大蠊(Periplanetajaponica)、棕色蜚蠊(Periplaneta brunnea)、Periplaneta fuligginosa、澳洲蜚蠊(Periplaneta australasiae)和东方蜚蠊(Blatta orientalis),
蝇、蚊(双翅目(Diptera)),例如埃及伊蚊(Aedes aegypti)、白纹伊蚊(Aedesalbopictus)、刺扰伊蚊(Aedes vexans)、墨西哥果蝇(Anastrepha ludens)、五斑按蚊(Anopheles maculipennis)、Anopheles crucians、白足按蚊(Anopheles albimanus)、冈比亚按蚊(Anopheles gambiae)、Anopheles freeborni、海南岛白踝按蚊(Anophelesleucosphyrus)、云南微小按蚊(Anopheles minimus)、四斑按蚊(Anophelesquadrimaculatus)、红头丽蝇(Calliphora vicina)、蛆症金蝇(Chrysomya bezziana)、Chrysomya hominivorax、Chrysomya macellaria、鹿蝇(Chrysops discalis)、Chrysopssilacea、Chrysops atlanticus、螺旋蝇(Cochliomyia hominivorax)、Cordylobiaanthropophaga、狂怒库蠓(Culicoides furens)、尖音库蚊(Culex pipiens)、斑蚊(Culexnigripalpus)、致倦库蚊(Culex quinquefasciatus)、媒斑蚊(Culex tarsalis)、Culisetainornata、Culiseta meianura、Dermatobia hominis、小毛厕蝇(Fannia canicularis)、马蝇(Gasterophilus intestinalis)、刺舌蝇(Glossina morsitans)、须舌蝇(Glossinapalpalis)、Glossina fuscipes、胶舌蝇(Glossina tachinoides)、Haematobia irritans、Haplodiplosis equestris、潜蝇属(Hippelates spp.)、纹皮蝇(Hypoderma lineata)、Leptoconops torrens、Lucilia caprina、铜绿蝇(Lucilia cuprina)、丝光绿蝇(Luciliasericata)、Lycoria pectoralis、曼蚊属(Mansonia spp.)、家蝇(Musca domestica)、厩腐蝇(Muscina stabulans)、羊狂蝇(Oestrus ovis)、银足白蛉(Phlebotomus argentipes)、Psorophora columbiae、Psorophora discolor、Prosimulium mixtum、赤尾麻蝇(Sarcophaga haemorrhoidalis)、肉蝇属(Sarcophaga sp.)、Simulium vittatum、厩螯蝇(Stomoxys calcitrans)、Tabanus bovinus、Tabanus atratus、红色原虻(Tabanuslineola)和Tabanus similis,
虱(毛虱目(Phthiraptera)),例如人头虱(Pediculus humanus capitis)、人体虱(Pediculus humanus corporis)、阴虱(Pthirus pubis)、牛血虱(Haematopinuseurysternus)、猪血虱(Haematopinus suis)、牛颚虱(Linognathus vituli)、Bovicolabovis、鸡虱(Menopon gallinae)、Menacanthus stramineus和Solenopotes capillatus。
扁虱和寄生螨类(寄螨目(Parasitiformes)):蜱(蜱目(Ixodida)),例如黑脚硬蜱(Ixodes scapularis)、全环硬蜱(Ixodes holocyclus)、太平洋硬蜱(Ixodes pacificus)、Rhiphicephalus sanguineus、安氏革蜱(Dermacentor andersoni)、美洲大革蜱(Dermacentor variabilis)、长星形壁虱(Amblyomma americanum)、Ambryommamaculatum、Ornithodorus hermsi、Ornithodorus turicata和寄生性螨类(中气门目(Mesostigmata)),例如柏氏禽刺螨(Ornithonyssus bacoti)和鸡皮刺螨(Dermanyssusgallinae),
幅螨亚目(Actinedida)(前气门目(Prostigmata))和粉螨亚目(Acaridida)(无气门目(Astigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、Ornithocheyletia spp.、Myobia spp.、Psorergates spp.、毛囊虫属(Demodex spp.)、恙螨属(Trombicula spp.)、Listrophorus spp.、粉螨属(Acarus spp.)、食酪螨属(Tyrophagus spp.)、嗜木螨属(Caloglyphus spp.)、Hypodectes spp.、Pterolichusspp.、痒螨属(Psoroptes spp.)、足螨属(Chorioptes spp.)、耳痒螨属(Otodectes spp.)、疥螨属(Sarcoptes spp.)、痂螨属(Notoedres spp.)、膝螨属(Knemidocoptes spp.)、Cytodites spp.和Laminosioptes spp,
臭虫(半翅目(Heteropterida)):温带臭虫(Cimex lectularius)、热带臭虫(Cimex hemipterus)、Reduvius senilis、Triatoma属、红猎蝽属(Rhodnius spp.)、Panstrongylus属和Arilus critatus,
Anoplurida,例如血虱属(Haematopinus spp.)、颚虱属(Linognathus spp.)、人虱属(Pediculus spp.)、Phtirus spp.和管虱属(Solenopotes spp.),
Mallophagida(Arnblycerina和Ischnocerina亚目),例如Trimenopon spp.、鸡虱属(Menopon spp.)、鸭虱属(Trinoton spp.)、绵羊虱属(Bovicola spp.)、Werneckiellaspp.、Lepikentron spp.、啮毛虱属(Trichodectes spp.)和猫毛虱属(Felicola spp.),
蛔虫线虫类:
Wipeworms和旋毛虫病(Trichinosis)(Trichosyringida),例如毛形虫科(Trichinellidae)(旋毛形线虫属(Trichinella spp.))、(鞭虫科(Trichuridae))鞭虫属(Trichuris spp.)、毛细线虫属(Capillaria spp),
杆形目(Rhabditida),例如小杆线虫属(Rhabditis spp)、粪杆线虫属(Strongyloides spp.)、Helicephalobus spp,
圆线虫目(Strongylida),例如圆线虫属(Strongylus spp.)、钩口线虫属(Ancylostoma spp.)、美洲板口线虫(Necator americanus)、仰口线虫(Bunostomum spp.)(钩虫)、毛圆线虫属(Trichostrongylus spp.)、捻转血矛线虫(Haemonchus contortus.)、胃线虫属(Ostertagia spp.)、库珀线虫属(Cooperia spp.)、细颈属(Nematodirus spp.)、网尾线虫属(Dictyocaulus spp.)、盅口属(Cyathostoma spp.)、食道口线虫属(Oesophagostomum spp.)、有齿冠尾线虫(Stephanurus dentatus)、猪盘头线虫(Ollulanus spp.)、夏伯特线虫属(Chabertia spp.)、有齿冠尾线虫(Stephanurusdentatus)、气管比翼线虫(Syngamus trachea)、钩虫线虫属(Ancylostoma spp.)、钩虫属(Uncinaria spp.)、球首属(Globocephalus spp.)、板口线虫属(Necator spp.)、后圆属(Metastrongylus spp.)、缪勒属线虫(Muellerius capillaris)、原圆属(Protostrongylus spp.)、血管团线虫属(Angiostrongylus spp.)、Parelaphostrongylusspp.、Aleurostrongylus abstrusus和肾膨结线虫(Dioctophyma renale),
肠内蛔虫(Ascaridida),例如似蚓蛔线虫(Ascaris lumbricoides)、猪蛔虫(Ascaris suum)、鸡蛔虫(Ascaridia galli)、马蛔虫(Parascaris equorum)、蛲虫(Enterobius vermicularis)(绕虫)、犬蛔虫(Toxocara canis)、狮弓蛔虫(Toxascarisleonine)、斯氏虫属(Skrjabinema spp.)和马尖尾线虫(Oxyuris equi),
驼形目(Camallanida),例如麦地那龙线虫(Dracunculus medinensis)(龙线虫),
旋尾目(Spirurida),例如吸吮线虫属(Thelazia spp.)、吴策线虫属(Wuchereriaspp.)、布鲁丝虫属(Brugia spp.)、盘尾丝虫属(Onchocerca spp.)、Dirofilari spp.a、双瓣丝虫属(Dipetalonema spp.)、狗尾草属(Setaria spp.)、丝绒虫属(Elaeophora spp.)、Spirocerca lupi和柔线属(Habronema spp.),
多刺有头蠕虫(Acanthocephala),例如Acanthocephalus spp.、猪巨吻棘头虫(Macracanthorhynchus hirudinaceus)和Oncicola spp,
真涡虫(Plathelminthes):
Flukes(吸虫(Trematoda)),例如Faciola spp.、Fascioloides magna、并殖属(Paragonimus spp.)、双腔属(Dicrocoelium spp.)、布氏姜片吸虫(Fasciolopsisbuski)、华支睾吸虫(Clonorchis sinensis)、裂体属(Schistosoma spp.)、毛毕属(Trichobilharzia spp.)、有翼翼形吸虫(Alaria alata)、肺吸虫属(Paragonimus spp.)和Nanocyetes spp,
Cercomeromorpha,尤其是绦虫类(绦虫类(Tapeworms)),例如裂头属(Diphyllobothrium spp.)、Tenia spp.、棘球绦虫属(Echinococcus spp.)、犬复孔绦虫(Dipylidium caninum)、多头绦虫属(Multiceps spp.)、膜壳属(Hymenolepis spp.)、中殖孔绦虫属(Mesocestoides spp.)、Vampirolepis spp.、莫尼茨属(Moniezia spp.)、裸头属(Anoplocephala spp.)、Sirometra spp.、裸头属(Anoplocephala spp.)和膜壳属(Hymenolepis spp.)。
式I化合物和包含它们的组合物特别可用于防治来自双翅目(Diptera)、蚤目(Siphonaptera)和蜱目(Ixodida)目的害虫。
此外,尤其优选的是式I化合物和包含它们的组合物在对抗蚊子中的用途。
式I化合物和包含它们的组合物在对抗蝇中的用途是本发明的另一优选实施方案。
此外,尤其优选式I化合物和包含它们的组合物在对抗跳蚤中的用途。
式I化合物和包含它们的组合物在对抗扁虱中的用途是本发明的另一优选实施方案。
式I化合物还尤其可用于对抗体内寄生虫(蛔虫线虫、棘头虫和真涡虫)。
给药既可预防性地进行,也可治疗性地进行。
活性化合物的给药直接或以适合的制剂形式口服、局部/皮肤或肠道外进行。
对于温血动物的口服给药,可以将式I的化合物配制成动物饲料、动物饲料预混物、动物饲料浓缩物、丸剂、溶液、糊、悬浮液、顿服药、凝胶、片剂、大丸剂(boluses)和胶囊。另外,式I化合物可以在饮用水中给药于动物。对于口服给药,所选剂量应给动物提供0.01mg/kg至100mg/kg动物体重/天的式I化合物,优选0.5mg/kg至100mg/kg动物体重/天。
或者,式I化合物可肠道外给药于动物,例如通过瘤胃(intraruminal)、肌内、静脉内或皮下注射。对于皮下注射,式I化合物可分散或溶解于生理可接受载体中。或者,式I化合物可配制成皮下给药用植入物。另外,式I化合物可透皮给药于动物。对于肠道外给药,选择的剂量应提供给动物0.01mg/kg至100mg/kg动物体重/天的式I化合物。
式I化合物也可以以浸液(dips)、粉剂、粉末、项圈、挂牌(medallions)、喷剂、洗发剂、蘸点(spot-on)和浇泼(pour-on)配制剂和软膏或水包油或油包水乳液的形式局部施用于动物。对于局部施用,浸液和喷剂通常包含0.5ppm至5,000ppm,优选1ppm至3,000ppm式I化合物。另外,式I化合物可配制成动物,特别是四足动物如牛和绵羊用耳标。
适合的制剂为:
-溶液如口服溶液、稀释以后用于口服给药的浓缩物、用于皮肤上或体腔中的溶液、浇泼配制剂、凝胶;
-口服或皮肤给药用的乳液和悬浮液;半固体制剂;
-其中活性化合物加工到软膏基中或水包油或油包水乳液基中的配制剂;
-固体制剂如粉末、预混物或浓缩物、颗粒、丸、片、大丸剂、胶囊;气溶胶和吸入剂,和含活性化合物的成型制品。
适于注射的组合物通过将活性成分溶于适合的溶剂中并任选加入其它成分如酸、碱、缓冲盐、防腐剂和增溶剂而制备。过滤溶液并无菌灌装。
适合的溶剂为生理可耐受溶剂如水,链烷醇如乙醇、丁醇、苄醇、甘油、丙二醇、聚乙二醇,N-甲基-吡咯烷酮,2-吡咯烷酮及其混合物。
活性化合物可任选溶于适于注射的生理可耐受植物或合成油中。
适合的增溶剂为促进活性化合物在主要溶剂中溶解或防止其沉淀的溶剂。实例为聚乙烯吡咯烷酮、聚乙烯醇、聚氧乙基化蓖麻油和聚氧乙基化脱水山梨糖醇酯。
适合的防腐剂为苄醇、三氯丁醇、对羟基苯甲酸酯和正丁醇。
口服溶液直接给药。浓缩物在预先稀释至使用浓度以后口服给药。口服溶液和浓缩物根据技术和如上关于注射溶液的描述而制备,其中不需要无菌程序。
用于皮肤上的溶液滴流、涂布、用力擦入、喷洒上或喷雾在皮肤上。
用于皮肤上的溶液根据技术并根据以上关于注射溶液的描述而制备,其中不需要无菌程序。
其它适合的溶剂为聚丙二醇,苯基乙醇,苯氧基乙醇,酯如乙酸乙酯或丁酯、苯甲酸苄酯,醚如亚烷基二醇烷基醚如二丙二醇单甲基醚,酮类如丙酮、甲基乙基酮,芳族烃,植物和合成油,二甲基甲酰胺,二甲基乙酰胺,transcutol,solketal,异丙二醇碳酸酯及其混合物。
在制备期间可有利地加入增稠剂。适合的增稠剂为无机增稠剂如膨润土、胶质硅酸、单硬脂酸铝,有机增稠剂如纤维素衍生物、聚乙烯醇和它们的共聚物、丙烯酸酯和甲基丙烯酸酯。
将凝胶施用于或涂布在皮肤上或引入体腔中。凝胶通过将已通过如在注射溶液情况下所述而制备的溶液用足够的增稠剂处理而制备,产生具有软膏状稠度的透明材料。所用增稠剂为上面给出的增稠剂。
浇泼配制剂浇泼在或喷在皮肤的限制区域上,活性化合物渗透皮肤并内吸起作用。
浇泼配制剂通过使活性化合物在适合的皮肤相容性的溶剂或溶剂混合物中溶解、悬浮或乳化而制备。如果适合的话,加入其它助剂如着色剂、生物吸收促进物质、抗氧化剂、光稳定剂、粘着剂。
适合的溶剂为:水,链烷醇,二醇,聚乙二醇,聚丙二醇,甘油,芳族醇如苄醇、苯基乙醇、苯氧基乙醇,酯如乙酸乙酯、乙酸丁酯、苯甲酸苄酯,醚如亚烷基二醇烷基醚如二丙二醇单甲基醚、二乙二醇单丁基醚,酮类如丙酮、甲基乙基酮,环状碳酸酯如异丙二醇碳酸酯、碳酸亚乙酯,芳族和/或脂族烃,植物或合成油,DMF,二甲基乙酰胺,正烷基吡咯烷酮如甲基吡咯烷酮、正丁基吡咯烷酮或正辛基吡咯烷酮,N-甲基吡咯烷酮,2-吡咯烷酮,2,2-二甲基-4-氧基-亚甲基-1,3-二氧-戊环和甘油缩甲醛。
适合的着色剂为允许用于动物上并且可溶解或悬浮的所有着色剂。
适合的吸收促进物质例如为DMSO,涂布油如肉豆蔻酸异丙酯、壬酸二丙二醇酯,硅油及其与聚醚的共聚物,脂肪酸酯、甘油三酸酯,脂肪醇。
适合的抗氧化剂为亚硫酸盐或焦亚硫酸盐如焦亚硫酸钾,抗坏血酸,丁基羟基甲苯,丁基羟基茴香醚,生育酚。
适合的光稳定剂例如为2-苯基苯并咪唑-5-磺酸(novantisolic acid)。
适合的粘着剂例如为纤维素衍生物、淀粉衍生物、聚丙烯酸酯、天然聚合物如藻酸盐、明胶。
乳液可口服给药、皮肤给药或作为注射剂给药。
乳液为油包水类型或水包油类型。
它们通过将活性化合物溶于疏水或亲水相中并与其它相的溶剂借助适合的乳化剂和如果合适的话其它助剂如着色剂、吸收促进物质、防腐剂、抗氧化剂、光稳定剂、增粘物质使其均化而制备。
适合的疏水相(油)为:
液体石蜡,硅油,天然植物油如芝麻油、杏仁油、蓖麻油,合成甘油三酸酯如辛酸/癸酸二甘油酯、具有链长C8-C12的植物脂肪酸或其它特别选择的天然脂肪酸的甘油三酸酯混合物,还可含羟基的饱和或不饱和脂肪酸的偏甘油酯混合物,C8-C10脂肪酸的单甘油酯和二甘油酯,
脂肪酸酯如硬脂酸乙酯、己二酸二正丁酰酯、月桂酸己酯、二丙二醇perlargonate,中等链长的支化脂肪酸与链长C16-C18的饱和脂肪醇的酯,肉豆蔻酸异丙酯、棕榈酸异丙酯,链长C12-C18的饱和脂肪醇的辛酸/癸酸酯,硬脂酸异丙酯、油酸油基酯、油酸癸酯、油酸乙酯、乳酸乙酯,蜡质脂肪酸酯如合成鸭尾脂腺脂肪,邻苯二甲酸二丁酯,己二酸二异丙酯,和涉及后者的酯混合物,脂肪醇如异十三醇、2-辛基十二醇、鲸蜡基硬脂基醇、油醇,和脂肪酸如油酸及其混合物。
适合的亲水相为:水,醇如丙二醇、甘油、山梨糖醇及其混合物。
适合的乳化剂为:
非离子表面活性剂如聚乙氧基化蓖麻油、聚乙氧基化脱水山梨糖醇单油酸酯、脱水山梨糖醇单硬脂酸酯、甘油单硬脂酸酯、聚氧乙基硬脂酸酯、烷基酚聚二醇醚;
两性表面活性剂如N-月桂基-p-亚氨基二丙酸二-钠或卵磷脂;
阴离子表面活性剂如月桂基硫酸钠、脂肪醇醚硫酸盐、单/二烷基聚二醇醚正磷酸酯单乙醇胺盐;
阳离子活性表面活性剂如鲸蜡基三甲基氯化铵。
适合的其它助剂为:增强粘度和稳定乳液的物质,例如羧甲基纤维素、甲基纤维素和其它纤维素和淀粉衍生物、聚丙烯酸酯、藻酸盐、明胶、阿拉伯胶、聚乙烯吡咯烷酮、聚乙烯醇、甲基乙烯基醚与马来酸酐的共聚物、聚乙二醇、蜡、胶质硅酸或所述物质的混合物。
悬浮液可口服或局部/皮肤给药。它们通过使活性化合物在悬浮剂中悬浮,如果合适的话加入其它助剂如润湿剂、着色剂、生物吸收促进物质、防腐剂、抗氧化剂、光稳定剂而制备。
液体悬浮剂为所有均质溶剂和溶剂混合物。
适合的润湿剂(分散剂)为以上给出的乳化剂。
可提到的其它助剂为以上给出的那些。
半固体制剂可口服或局部/皮肤给药。它们不同于上述悬浮液和乳液之处在于它们的更高粘度。
为制备固体制剂,将活性化合物与适合的赋形剂混合,如果合适的话加入助剂,并形成所需形式。
适合的赋形剂为所有生理可耐受的固体惰性物质。所用那些为无机和有机物质。无机物质例如为氯化钠、碳酸盐如碳酸钙、碳酸氢盐、氧化铝、氧化钛、硅酸、粘土、沉淀或胶态氧化硅或磷酸盐。有机物质例如为糖、纤维素、食品和饲料如奶粉、动物粉、谷粉和谷碎、淀粉。
适合的助剂为防腐剂、抗氧化剂和/或上述着色剂。
其它适合的助剂为润滑剂和助流剂如硬脂酸镁、硬脂酸、滑石、膨润土、促崩解物质如淀粉或交联聚乙烯吡咯烷酮、粘合剂如淀粉、明胶或线性聚乙烯吡咯烷酮,和干粘合剂如微晶纤维素。
一般而言,“杀寄生虫有效量”意指对生长实现可观察到的效力,包括坏死、死亡、阻滞、防止和除去、破坏或减少目标有机体的出现和活性的效力所需的活性成分量。对于本发明所用各种化合物/组合物,杀寄生虫有效量可变化。组合物的杀寄生虫有效量也可根据主导条件如所需的杀寄生虫效力和持续时间、目标种、施用模式等变化。
可用于本发明的组合物可通常包含约0.001-95%式I化合物。
一般而言,有利的是以0.5mg/kg至100mg/kg每天,优选1mg/kg至50mg/kg每天的总量施用式I化合物。
即用制剂以10ppm至80重量%,优选0.1-65重量%,更优选1-50重量%,最优选5-40重量%的浓度包含对寄生虫,优选体外寄生虫起作用的化合物。
在使用以前稀释的制剂以0.5-90重量%,优选1-50重量%的浓度含有对体外寄生虫起作用的化合物。
此外,制剂以10ppm至2重量%,优选0.05-0.9重量%,非常特别优选0.005-0.25重量%的浓度包含对抗体内寄生虫的式I化合物。
在本发明一个优选实施方案中,包含式I化合物的组合物皮肤/局部施用。
在另一优选实施方案中,局部施用以包含化合物的成型制品如项圈、挂牌(medallions)、耳标、固定在身体部分的带,和粘合条和箔的形式进行。
一般而言,有利的是施用在三星期期间以10mg/kg至300mg/kg,优选20mg/kg至200mg/kg,最优选25mg/kg至160mg/kg处理动物的体重的总量释放式I化合物的固体配制剂。
为制备成型制品,使用热塑性和柔性塑料以及弹性体和热塑性弹性体。适合的塑料和弹性体为与I化合物充分相容的聚乙烯基树脂、聚氨酯、聚丙烯酸酯、环氧树脂、纤维素、纤维素衍生物、聚酰胺和聚酯。塑料和弹性体以及成型制品的制备程序的详情例如在WO03/086075中给出。
实施例
现在通过以下实施例进一步详细阐述本发明,而不施以任何限制。
S.合成实施例
合成实施例S.1:N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-3-甲氧基-丙酰胺(实施例化合物E1.3)
步骤1:制备1-[(6-氯-3-吡啶基)甲基]吡啶-1--2-胺氯化物(中间体化合物IE.1)]
将2-氯-5-氯-甲基吡啶(16.20g,100毫摩尔)和2-氨基-吡啶(9.60g,102毫摩尔)在乙醇(100mL)中的溶液回流24小时。然后将反应冷却至室温并在真空中浓缩。然后将100mL苯基甲基加入残余物中,并将混合物在真空中浓缩。将75mL CH2Cl2加入残余物中并将混合物快速搅拌15分钟,在此期间形成沉淀物。然后将沉淀物过滤,并用CH2Cl2(50mL)、二乙醚(50mL)洗涤并在真空下干燥,得到浅黄色固体产物1-[(6-氯-3-吡啶基)甲基]吡啶-1--2-胺氯化物IE.1(14.0g,55%收率)。
LC-MS:C11H11ClN3[M]+的计算质量220.1,发现值220.1;tR=0.529分钟。
步骤2:制备N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-3-甲氧基-丙酰胺(实施例化合物E1.3)
在0℃下向1-[(6-氯-3-吡啶基)甲基]吡啶-1--2-胺氯化物胺盐IE.1(0.250g,0.97毫摩尔)、3-甲氧基丙酸(0.132g,1.26毫摩尔)和三乙胺(0.267g,2.63毫摩尔)在CH2Cl2(8mL)中的溶液中加入丙基磷酸酐溶液(50重量%)(0.496g,1.55毫摩尔,1mL 50重量%的EtOAc溶液)。然后使反应回温至室温,并搅拌60小时。将反应用EtOAc(200mL)稀释,用饱和含水NaHCO3洗涤,层分离,将有机层经Na2SO4干燥并在真空中浓缩,得到米色固体所需产物E1.3(0.120g,40%收率)。
LC-MS:C15H17ClN3O2[M+H]+计算质量306.1,发现值306.1;tR=0.630分钟。
合成实施例S.2:N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2-甲硫基-乙酰胺(实施例化合物E1.9)
在0℃下向中间体胺盐IE.1(1.30g,5.08毫摩尔)、甲硫基乙酸(0.70g,6.60毫摩尔)和三乙胺(1.39g,13.70毫摩尔)在CH2Cl2(15mL)中的溶液中加入PPA溶液(50重量%)(2.58g,1.60毫摩尔,5mL 50重量%的EtOAc溶液)。然后使反应回温至室温,并搅拌60小时。将反应用EtOAc(200mL)稀释,用饱和含水NaHCO3洗涤,层分离,将有机层经Na2SO4干燥并在真空中浓缩,得到残余物。将残余物使用硅胶层析用100%EtOAc洗脱,然后用4%MeOH/CH2Cl2洗脱而提纯,得到米色固体所需产物E1.9(0.750g,46%收率)。HRMS(ESI,Na):C11H18N2O3Na(M+Na)+的m/z计算值249.1210,
LC-MS:C14H15ClN3OS[M+H]+计算质量308.1,发现值308.1;tR=0.611分钟。
合成实施例S.3:N-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-2-甲基磺酰基-乙酰胺(实施例化合物E1.10)
在0℃下向酰胺E1.9(0.400g,1.300毫摩尔)在CH2Cl2(7mL)中的溶液以一份加入mCPBA(0.750g,3.250毫摩尔)。将反应搅拌20分钟,然后在沉淀物形成时变得极稠,然后加入7mL CH2Cl2。然后将反应在室温下搅拌6小时,然后用饱和含水NaHCO3(100mL)稀释,用EtOAc(200mL)萃取,将有机层经Na2SO4干燥,过滤并在真空中浓缩。将所得残余物使用硅胶层析用100%EtOAc洗脱,然后用4%MeOH/CH2Cl2洗脱而提纯,得到米色固体所需产物E1.10(0.300g,84%收率)。
LC-MS:C14H15ClN3O3S[M+H]+计算质量340.0,发现值340.0;tR=0.621分钟。
C.化合物实施例
根据本发明的一些化合物实施例与其物理数据一起显示于下表中,并在下文中说明其生物活性。
化合物实施例可通过其物理-化学数据*),例如通过联合高效液相色谱、质谱(HPLC/MS)或其熔点表征。
*)分析UPLC柱:Phenomenex Kinetex 1.7μm XB-C18 100A;50×2.1mm;流动相:A:水+0.1%三氟乙酸(TFA);B:乙腈+0.1%TFA;梯度:1.50分钟内5-100%B;100%B 0.20分钟;流速:在1.50分钟内在60℃下0.8-1.0mL/min。
MS-方法:ESI positive。
根据本发明的式E1化合物的实施例和数据在下表E1中给出。
下式的化合物实施例与其物理化学数据一起在此处的下表E1中给出。
表E1:
a)#表示与分子的其余部分的连接点;
*)分析UPLC柱(参见下文)
在以下实施例和表E中,Het根据下表表示:
E2下式的化合物实施例与其物理化学数据一起在此处的下表E2中给出。
E3.下式的化合物实施例及其物理化学数据在此处的下表E3中给出。
表E3:
E4.下式的化合物实施例及其物理化学数据在此处的下表E4中给出。
表E4:
No. | Het | R1 | R2 | R3a | R4a | R5 | X | Y | RT[min] | m/z[MH]+ |
E4-1 | Het1A | H | H | H | H | CH2CH3 | O | S | NA | NA |
E5.下式的化合物实施例及其物理化学数据在此处的下表E5中给出。
表E5:
No. | Het | R1 | R2 | R3a | R4a | R5 | X | RT[min] | m/z[MH]+ |
E5-1 | Het1A | H | H | H | H | CH2CH3 | O | 0.750 | 346.5 |
B.生物实施例
本发明式I化合物的生物活性可在如下文所述的生物试验中评估。
一般条件:如果没有另外说明,所述试验溶液如下制备:将活性化合物以所需浓度溶于1∶1(vol∶vol)蒸馏水∶丙酮混合物中。另外,试验溶液在使用当天制备(并且如果没有另外说明,浓度通常为重量/体积)。
B.1桃蚜(Myzus persicae)
活性化合物通过Tecan液体处理器在100%环己酮中配制成在管中提供的10,000ppm溶液。将该10,000ppm溶液在100%环己酮中连续地稀释以制备过渡溶液。这些用作通过储液,将其通过Tecan在50%丙酮∶50%水(v/v)中进行最终稀释放入5或10ml玻璃瓶中。非离子表面活性剂以0.01%(v/v)的体积包含在溶液中。然后将小瓶插入装配有雾化喷嘴的自动化静电喷雾器中以施用于植物/昆虫。
在处理以前通过将来自主群的被重度侵染的叶子放在处理植物顶部而将第一真叶期的柿子椒植物侵染。使蚜虫转移一整夜以实现30-50只蚜虫每植物的侵染,并除去宿主叶子。然后通过装配有雾化喷嘴的自动化静电植物喷雾器对受侵染的植物喷雾。将植物在喷雾器通风橱中干燥,取出,然后在生长室中在约25℃和约20-40%相对湿度下在荧光照明下保持24小时光照期。在5天以后测定相对于未处理对照植物的处理植物上的蚜虫死亡率。
在该试验中,如下化合物在2500ppm下显示出与未处理对照相比至少75%死亡率:E1-6,E1-7,E1-8,E1-9,E1-10,E2-1,E2-2,E2-3,E2-4,E2-5,E2-6,E2-7,E2-8,E2-9,E2-10,E2-11,E2-12,E2-13,E2-14,E2-15,E2-16,E2-17,E2-18,E2-19,E2-20,E2-21,E2-22,E2-26,E2-27,E2-28,E2-30,E2-31,E2-32,E2-33,E2-34,E2-35,E2-36,E2-37,E2-38,E2-42,E2-44,E2-45,E2-46,E2-50,E2-51,E2-53,E2-54,E2-55,E2-57,E2-58,E2-59,E2-60,E2-62,E2-63,E2-64,E2-66,E2-67,E2-69,E2-70,E2-71,E2-72,E2-74,E2-75,E2-76,E2-77,E2-78,E2-79,E2-80,E2-82,E2-83,E2-84,E2-87,E2-88,E2-89,E2-90,E2-91,E2-92,E2-95,E2-97,E2-98,E2-99,E2-100,E2-101,E2-102,E2-103,E2-104,E2-105,E2-108,E2-109,E2-110,E2-111,E2-112,E2-113,E2-114,E2-120,E2-121,E2-122,E2-123,E2-124,E2-125,E2-126,E2-127,E2-128,E2-129,E2-131,E2-132,E2-133,E2-134,E2-135,E2-138,E2-139,E2-140,E2-141,E2-142,E2-144,E2-145,E2-146,E2-147,E2-150,E2-152,E2-154,E2-155,E2-156,E2-157,E2-158,E2-159,E2-161,E2-163,E2-164,E2-165,E2-166,E2-167,E2-168,E2-169,E2-170,E2-171,E2-172,E2-173,E2-174,E2-175,E2-176,E2-177,E2-178,E2-179,E2-180,E2-181,E2-182,E2-183,E2-184,E2-185,E2-187,E2-188,E2-189,E2-191,E2-192,E2-193,E2-194,E2-195,E2-196,E2-200,E2-201,E2-203,E2-205,E2-207,E2-208,E2-209,E2-211,E3-1,E3-2,E3-5,E3-6,E3-7,E3-8,E3-9,E4-1和E5-1。
B.2蚕豆修尾蚜(Megoura viciae)
对于评估通过接触或内吸措施防治蚕豆修尾蚜(Megoura viciae),试验装置由包含蚕豆叶片的24-孔微滴定板组成。
将化合物使用包含75%v/v水和25%v/v DMSO的溶液配制。使用定制的微型雾化器将不同浓度的配制化合物以2.5μl喷雾在叶片上,喷两次。
在施用以后,将叶片风干并将5-8个蚜虫成虫放在微滴定板孔内的叶片上。然后使蚜虫吸吮处理的叶片并在约23±1℃和约50±5%相对湿度下接种5天。然后视觉评估蚜虫死亡率和繁殖力。
在该试验中,如下化合物在2500ppm下显示出与未处理对照相比至少75%死亡率:E1-6,E1-8,E1-9,E1-10,E2-1,E2-2,E2-3,E2-4,E2-5,E2-6,E2-7,E2-8,E2-9,E2-10,E2-11,E2-12,E2-13,E2-14,E2-15,E2-16,E2-17,E2-19,E2-20,E2-21,E2-24,E2-27,E2-28,E2-31,E2-33,E2-34,E2-36,E2-44,E2-45,E2-50,E2-51,E2-53,E2-55,E2-57,E2-58,E2-59,E2-63,E2-66,E2-69,E2-71,E2-72,E2-74,E2-75,E2-76,E2-82,E2-87,E2-95,E2-98,E2-99,E2-104,E2-105,E2-109,E2-110,E2-111,E2-112,E2-114,E2-120,E2-121,E2-124,E2-125,E2-126,E2-127,E2-128,E2-129,E2-131,E2-132,E2-135,E2-138,E2-139,E2-140,E2-141,E2-142,E2-145,E2-146,E2-147,E2-150,E2-152,E2-154,E2-155,E2-156,E2-157,E2-158,E2-159,E2-163,E2-164,E2-165,E2-166,E2-167,E2-168,E2-169,E2-170,E2-171,E2-172,E2-173,E2-174,E2-176,E2-177,E2-178,E2-179,E2-180,E2-181,E2-182,E2-183,E2-184,E2-185,E2-187,E2-188,E2-189,E2-191,E2-192,E2-194,E2-195,E2-200,E2-203,E2-205,E2-207,E2-208,E2-209,E2-211,E3-1,E3-2,E3-5,E3-6,E3-8,E3-9,E4-1和E5-1。
B.3棉蚜(Aphis gossypii)
活性化合物通过Tecan液体处理器在100%环己酮中配制成在管中提供的10,000ppm溶液。将该10,000ppm溶液在100%环己酮中连续地稀释以制备过渡溶液。这些用作通过储液,将其通过Tecan在50%丙酮∶50%水(v/v)中进行最终稀释放入5或10ml玻璃瓶中。非离子表面活性剂以0.01%(v/v)的体积包含在溶液中。然后将小瓶插入装配有雾化喷嘴的自动化静电喷雾器中以施用于植物/昆虫。
在处理以前通过将来自主蚜虫群落的被重度侵染的叶片放在各个子叶的顶部而将子叶期的棉花植物用蚜虫侵染。使蚜虫转移整夜以实现80-100只蚜虫每植物的侵染,并除去宿主叶。然后通过装配有雾化喷嘴的自动化静电植物喷雾器对受侵染的植物喷雾。将植物在喷雾器通风橱中干燥,从喷雾器中取出,然后在生长室中在约25℃和约20-40%相对湿度下在荧光照明下保持24小时光照期。在5天以后测定相对于未处理对照植物的处理植物上的蚜虫死亡率。
在该试验中,化合物E1-8、E2-4、E2-14、E2-139、E2-154、E2-155、E2-159和E2-184在500ppm下显示出与未处理对照相比至少75%死亡率。
B.4豇豆蚜(Aphis craccivora)
将活性化合物以所需浓度溶于1∶1(vol∶vol)蒸馏水∶丙酮混合物中。以0.1%(vol/vol)的比例加入表面活性剂(EL 620)。试验溶液在使用当天制备。
在施用以前,通过手动转移从受侵染植物上切下的叶组织而将盆栽的豇豆植物用约50-100只各阶段的蚜虫拓殖24小时。在记录害虫数量以后将植物喷雾。将处理的植物在轻型推车上保持在约28℃下。在72小时以后评估%死亡率。
在该试验中,如下化合物在500ppm下显示出与未处理对照相比至少75%死亡率:E1-6,E1-8,E1-9,E1-10,E2-2,E2-3,E2-4,E2-5,E2-6,E2-7,E2-8,E2-9,E2-12,E2-13,E2-14,E2-15,E2-16,E2-17,E2-19,E2-20,E2-21,E2-26,E2-28,E2-34,E2-51,E2-57,E2-58,E2-59,E2-61,E2-66,E2-71,E2-74,E2-75,E2-76,E2-82,E2-95,E2-98,E2-99,E2-101,E2-105,E2-107,E2-111,E2-112,E2-113,E2-114,E2-115,E2-120,E2-124,E2-125,E2-126,E2-127,E2-128,E2-129,E2-131,E2-133,E2-138,E2-139,E2-141,E2-142,E3-1,E3-2,E3-5,E3-6,E3-7,E3-8,E3-9,E4-1,和E5-1。
B.5银叶粉虱(bemisia argentifolii)
活性化合物通过Tecan液体处理器在100%环己酮中配制成在管中提供的10,000ppm溶液。将该10,000ppm溶液在100%环己酮中连续地稀释以制备过渡溶液。这些用作通过储液,将其通过Tecan在50%丙酮∶50%水(v/v)中进行最终稀释放入5或10ml玻璃瓶中。非离子表面活性剂以0.01%(v/v)的体积包含在溶液中。然后将小瓶插入装配有雾化喷嘴的自动化静电喷雾器中以施用于植物/昆虫。
通过装配有雾化喷嘴的自动化静电植物喷雾器对子叶期的棉花植物(每盆一棵植物)喷雾。将植物在喷雾器通风橱中干燥,然后从喷雾器中取出。将各个盆放入塑料杯中并引入约10-12只粉虱成虫(约3-5天龄)。使用吸出器和与屏障吸移管端部连接的无毒管收集昆虫。然后将包含收集的昆虫的端部温和地插入包含处理植物的土壤中,使昆虫从端部中爬出以到达叶面取食。将杯子用可再用屏蔽盖盖上。将试验植物在生长室中在约25℃和约20-40%相对湿度下保持3天,避免直接暴露于荧光灯(24小时光照期)下以防止热捕集在杯中。在处理以后3天评估与未处理对照植物相比的死亡率。
在该试验中,化合物E1-8、E2-4、E2-5、E2-9、E2-14、E2-139、E2-143、E2-147、E2-155和E2-189在500ppm下显示出与未处理对照相比至少75%的死亡率。
B.6兰花蓟马(dichromothrips corbetti)
用于生物试验的兰花蓟马由连续保持在实验室条件下的群落得到。为了试验,将试验化合物在丙酮∶水(vol∶vol)的1∶1混合物加0.01%vol/volEL 620表面活性剂中稀释。
通过使用花卉浸渍技术评估各化合物的蓟马效力。将塑料陪替氏培养皿用作试验台。将各个完整兰花的所有花瓣浸入处理溶液中并使其干燥。将处理的花与约20只蓟马成虫一起放入各陪替氏培养皿中。然后将陪替氏培养皿用盖子盖上。在试验持续期间中,将所有试验台保持在连续光和约28℃的温度下。在3天以后,计数各个花以及各陪替氏培养皿内壁上的活蓟马数目。在处理以后72小时记录死亡率百分数。
在该试验中,如下化合物在500ppm下显示出与未处理对照相比至少75%的死亡率:E1-8,E1-10,E2-2,E2-4,E2-5,E2-6,E2-7,E2-9,E2-11,E2-12,E2-14,E2-15,E2-16,E2-17,E2-19,E2-20,E2-21,E2-25,E2-28,E2-32,E2-35,E2-45,E2-46,E2-47,E2-48,E2-50,E2-51,E2-56,E2-58,E2-59,E2-61,E2-64,E2-66,E2-71,E2-72,E2-74,E2-75,E2-76,E2-77,E2-79,E2-80,E2-82,E2-86,E2-91,E2-95,E2-98,E2-99,E2-107,E2-113,E2-114,E2-117,E2-120,E2-124,E2-126,E2-128,E2-129,E2-131,E2-133,E2-138,E2-139,E2-140,E3-5,E3-6,E3-9,E4-1和E5-1。
B.7稻绿叶蝉(Nephotettix virescens)
在喷雾前24小时将稻秧苗清洗。活性化合物在50∶50丙酮∶水(vol∶vol)中配制,并加入0.1%vol/vol表面活性剂(EL 620)。将盆栽的稻秧苗用5ml试验溶液喷雾,风干,放入笼中并用10只成虫接种。将处理的稻植物保持在约28-29℃和约50-60%的相对湿度下。在72小时以后记录死亡率百分数。
在该试验中,如下化合物在500ppm下显示出与未处理对照相比至少75%的死亡率:E1-6,E1-8,E1-9,E1-10,E2-3,E2-4,E2-5,E2-6,E2-7,E2-8,E2-9,E2-10,E2-11,E2-12,E2-14,E2-15,E2-16,E2-17,E2-19,E2-20,E2-21,E2-28,E2-34,E2-35,E2-45,E2-50,E2-51,E2-53,E2-56,E2-57,E2-58,E2-59,E2-71,E2-74,E2-75,E2-76,E2-82,E2-98,E2-112,E2-114,E2-116,E2-117,E2-118,E2-120,E2-121,E2-124,E2-125,E2-126,E2-127,E2-128,E2-129,E2-131,E2-132,E2-134,E2-135,E2-136,E2-138,E2-139,E2-141,E2-142,E2-144,E3-2,E3-5,E3-6,E3-9和E4-1。
B.8稻褐飞虱(Nilaparvata lugens)
在喷雾前24小时将稻秧苗清洗。活性化合物在50∶50丙酮∶水(vol∶vol)中配制,并加入0.1%vol/vol表面活性剂(EL 620)。将盆栽的稻秧苗用5ml试验溶液喷雾,风干,放入笼中并用10只成虫接种。将处理的稻植物保持在约28-29℃和约50-60%的相对湿度下。在72小时以后记录死亡率百分数。
在该试验中,如下化合物在500ppm下显示出与未处理对照相比至少75%的死亡率:E1-6,E1-9,E1-10,E2-3,E2-4,E2-5,E2-6,E2-7,E2-8,E2-9,E2-12,E2-13,E2-14,E2-15,E2-17,E2-19,E2-20,E2-21,E2-28,E2-34,E2-35,E2-45,E2-50,E2-51,E2-56,E2-57,E2-58,E2-59,E2-71,E2-74,E2-75,E2-76,E2-98,E2-114,E2-120,E2-126,E2-129,E2-131,E2-133,E2-135,E2-139,E2-142,E3-5,E3-6和E4-1。
B.9棉铃象鼻虫(墨西哥棉铃象(Anthonomus grandis))
对于评估棉铃象鼻虫的防治,试验装置由包含昆虫食物和5-10个棉铃象鼻虫卵的96-孔-微滴定板组成。
将化合物使用包含75%v/v水和25%v/v DMSO的溶液配制。使用定制的微型雾化器将不同浓度的配制化合物以5μl喷雾在昆虫食物上,喷两次。
在施用以后,将微滴定板在约25±1℃和约75±5%相对湿度下接种5天。然后视觉评估卵和幼虫死亡率。
在该试验中,如下化合物在500ppm下显示出与未处理对照相比至少75%的死亡率:E2-2,E2-4,E2-6,E2-7,E2-14,E2-15,E2-17,E2-33,E2-39,E2-49,E2-53,E2-57,E2-66,E2-74,E2-82,E2-84,E2-99,E2-100,E2-110,E2-112,E2-113,E2-116,E2-122,E2-123,E2-126,E2-132,E2-154,E2-159,E2-180,E2-189和E2-195。
B.10地中海果蝇(地中海实蝇(Ceratitis capitata))
对于评估地中海果蝇的防治,试验装置由包含昆虫食物和50-80个地中海果蝇卵的微滴定板组成。
将化合物使用包含75%v/v水和25%v/v DMSO的溶液配制。使用定制的微型雾化器将不同浓度的配制化合物以5μl喷雾在昆虫食物上,喷两次。
在施用以后,将微滴定板在约28±1℃和约80±5%相对湿度下接种5天。视觉评估卵和幼虫死亡率。
在该试验中,如下化合物在2500ppm下显示出与未处理对照相比至少75%的死亡率:E2-3,E2-4,E2-7,E2-12,E2-15,E2-17,E2-35,E2-39,E2-46,E2-63,E2-66,E2-69,E2-72,E2-74,E2-76,E2-78,E2-92,E2-95,E2-97,E2-99,E2-100,E2-105,E2-107,E2-108,E2-109,E2-110,E2-121,E2-140,E2-159和E3-6。
B.11烟夜蛾(烟芽夜蛾(Heliothis virescens))
对于评估烟夜蛾的防治,试验装置由包含昆虫食物和15-25个烟夜蛾(H.virescens)卵的96-孔-微滴定板组成。
将化合物使用包含75%v/v水和25%v/v DMSO的溶液配制。使用定制的微型雾化器将不同浓度的配制化合物以10μl喷雾在昆虫食物上,喷两次。
在施用以后,将微滴定板在约28+1℃和约80+5%相对湿度下接种5天。视觉评估卵和幼虫死亡率。
在该试验中,如下化合物在2500ppm下显示出与未处理对照相比至少75%的死亡率:E2-2,E2-4,E2-13,E2-14,E2-15,E2-26,E2-44,E2-49,E2-51,E2-66,E2-105,E2-109,E2-110,E2-113,E2-116,E2-132,E2-153,E2-155,E2-156,E2-159,E2-193,E3-1和E3-2。
B.12小菜蛾(Plutella xylostella)
将活性化合物以所需浓度溶于1∶1(vol∶vol)蒸馏水∶丙酮混合物中。以0.1%(vol/vol)的比率加入表面活性剂(EL 620)。试验溶液在使用当天制备。
将卷心菜的叶子浸入试验溶液中并风干。将处理的叶子放入用湿滤纸衬垫的陪替式培养皿中并用10个三龄幼虫接种。在处理以后72小时记录死亡率。还使用0-100%的等级记录进食损害。
在该试验中,化合物E2-5、E2-6、E2-9、E2-19、E2-44、E2-49、E2-51、E2-58、E2-59、E2-113、E2-124和E2-145在500ppm下显示出与未处理对照相比至少75%的死亡率。
Claims (27)
1.用于防治和/或对抗动物害虫的式(I)的N-取代吡啶亚基羰基化合物和/或其对映体、非对映体、E/Z-异构体或者农业或兽用可接受盐:
其中:
p为选自0、1、2、3、4、5或6的整数;
X为O或S;
Y为O或S(O)m,其中m为0、1、2;
Het选自下式Het-1、Het-4、Het-11、Het-23、Het-24和Het-27的基团:
其中#表示式(I)中的键,且其中:
k为0、1或2;且
R6a各自相互独立地选自氢、卤素、氰基、C1-C6烷基、C3-C8环烷基、C2-C6烯基、C2-C6炔基且其中上述脂族和脂环族基团的碳原子可任选进一步相互独立地被一个或多个R7取代,
OR8、NR9aR9b、S(O)nR8、S(O)nNR9aR9b、C(=O)R7、C(=O)NR9aR9b、C(=O)OR8、C(=S)R7、C(=S)NR9aR9b、C(=NR9a)R7、C(=NR9a)NR9aR9b;W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成选自如下的饱和、不饱和或部分不饱和6员含氮杂环:W.Het-1:
其中#表示与分子其余部分的键;且其中:
Rw6选自氢;
R1、R2相互独立地选自氢、C1-C3烷基;
R3a、R3b各自相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基或OR8,其中脂族基团为未被取代的、部分或完全卤代的,或者
其中R3a、R3b与它们所结合的碳原子一起形成3、4、5元脂族环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的;
并且,如果p为1或更大,则R3a或R3b中的一个可与相邻碳原子的R4a或R4b形成双键,
R4a、R4b各自相互独立地且独立于整数p地选自氢、卤素、CN、C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基和C3-C8环烷基,其中最后提到的6个基团各自为未被取代的、部分或完全卤代的,
或者
其中R4a和R4b可一起形成=O、=CR13R14;=S,
或者如果p为1或更大,则R4a或R4b中的一个可与R3a或R3b或者与相邻碳原子的另一R4a或R4b形成双键,
R5选自氢、氰基、C1-C6烷基、C7-C12烷基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C3-C8环烷基、C3-C8环烷基硫基、C3-C8环烷基亚硫酰基、C3-C8环烷基磺酰基,其中上述脂族和脂环族基团的碳链原子为未被取代的、部分或完全卤代的或者可带有一个或多个基团R7的任意组合;
C(=O)R7、C(=S)R7;
苯基或CH2-苯基,其任选被1、2、3、4或5个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被q个独立于q且相互独立地选择的取代基Ry取代,且其中杂环的氮和/或硫原子可任选被氧化,其中杂环可直接结合在或者经由CH2基团连接在分子的其余部分上,且其中:
q为选自1、2、3或4的整数,且
Ry选自氢、卤素、氰基、硝基、C1-C10烷基、C2-C10烯基,其中上述脂族基团的碳原子可任选被一个或多个相互独立地选择的R15取代,
OR16、-S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)R15、C(=O)OR16、-C(=NR17a)R15、C(=O)NR17aR17b、C(=S)NR17aR17b,
或者
存在于部分饱和杂环的一个原子上的两个Ry一起可以为=O、=CR13R14、=NR17a、=NOR16或=NNR17a;
或者
相邻碳原子上的两个Ry可以为选自CH2CH2CH2CH2、CH=CH-CH=CH、N=CH-CH=CH、CH=N-CH=CH、N=CH-N=CH、CH2CH2CH2、CH=CHCH2、CH2CH2NR17a、CH2CH=N、CH=CH-NR17a的桥,并与这两个Ry所结合的碳原子一起形成5员或6员稠合的部分饱和或不饱和、芳族碳环或杂环,其中环可任选被1个或2个选自=O、OH、CH3、OCH3、卤素、氰基、卤代甲基或卤代甲氧基的取代基取代;
R7各自相互独立地选自氢、卤素、氰基、叠氮基、硝基、-SCN、SF5、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、Si(R11)2R12、OR16、OSO2R16、S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)NR17aR17b、C(=S)NR17aR17b、C(=O)OR16、C(=O)R15、C(=S)R15、C(=NR17a)R15,
苯基,其任选被1、2、3、4或5个相互独立地选择的取代基R10取代,3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化,
或者
存在于一个碳原子上的两个R7可一起形成=O、=CR13R14;=S;=NR17a、=NOR16;=NNR17a;
或者
两个R7可与这两个R7所结合的碳原子一起形成3-、4-、5-、6-、7-或8员饱和或部分不饱和碳环或杂环;
R8各自相互独立地选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、C3-C8环烷基、C4-C8烷基环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、-Si(R11)2R12、S(O)nR16、S(O)nNR17aR17b、NR17aR17b、-N=CR13R14、-C(=O)R15、C(=O)NR17aR17b、C(=S)NR17aR17b、C(=O)OR16,
苯基,其任选被一个或多个相互独立地选择的取代基R10取代,
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
R9a、R9b各自相互独立地选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基,
S(O)nR16、-S(O)nNR17aR17b、C(=O)R15、C(=O)OR16、C(=O)NR17aR17b、C(=S)R15、C(=S)SR16、C(=S)NR17aR17b、C(=NR17a)R15;
苯基,其任选被1、2、3或4个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2、3或4个选自氧、氮和/或硫的杂原子,任选被1、2、3或4个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
R9a和R9b一起为C2-C7亚烷基链并与它们所结合的氮原子一起形成3-、4-、5-、6-、7-或8员饱和、部分饱和或不饱和芳环,其中亚烷基链可包含1或2个选自氧、硫或氮的杂原子并且可任选被卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6卤代烷硫基、C3-C8环烷基、C3-C8卤代环烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基取代,
苯基,其任选被一个或多个相互独立地选择的取代基R10取代;
3-、4-、5-、6-或7员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被一个或多个相互独立地选择的取代基R10取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
R9a和R9b可一起形成=CR13R14、=NR17a或=NOR16基团;
R10各自相互独立地选自氢、卤素、氰基、叠氮基、硝基、SCN、SF5、C1-C10烷基、C3-C8环烷基、C2-C10烯基、C2-C10炔基,其中上述脂族和脂环族基团的碳原子可任选被一个或多个相互独立地选择的R15取代,
Si(R11)2R12、OR16、OS(O)nR16、-S(O)nR16、S(O)nNR17aR17b、NR17aR17b、C(=O)R15、C(=S)R15、C(=O)OR16、-C(=NR17a)R15、C(=O)NR17aR17b、C(=S)NR17aR17b,
苯基,其任选被卤素、氰基、硝基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基取代,
3-、4-、5-、6-或7-员饱和、部分饱和或不饱和芳族杂环,其包含1、2或3个选自氧、氮和/或硫的杂原子,任选被一个或多个独立地选自卤素、氰基、NO2、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基或C1-C6卤代烷氧基的取代基取代,且其中杂环的氮和/或硫原子可任选被氧化;
或者
一起存在于部分饱和杂环的一个原子上的两个R10可以为=O、=CR13R14;=NR17a、=NOR16或=NNR17a;
或者
相邻碳原子上的两个R10可以为选自CH2CH2CH2CH2、CH=CH-CH=CH、N=CH-CH=CH、CH=N-CH=CH、N=CH-N=CH、OCH2CH2CH2、OCH=CHCH2、CH2OCH2CH2、OCH2CH2O、OCH2OCH2、CH2CH2CH2、CH=CHCH2、CH2CH2O、CH=CHO、CH2OCH2、CH2C(=O)O、C(=O)OCH2、O(CH2)O、SCH2CH2CH2、SCH=CHCH2、CH2SCH2CH2、SCH2CH2S、SCH2SCH2、CH2CH2S、CH=CHS、CH2SCH2、CH2C(=S)S、C(=S)SCH2、S(CH2)S、CH2CH2NR17a、CH2CH=N、CH=CH-NR17a、OCH=N、SCH=N的桥,并与这两个R10所结合的碳原子一起形成5员或6员部分饱和或不饱和、芳族碳环或杂环,其中环可任选被1或2个选自=O、OH、CH3、OCH3、卤素、氰基、卤代甲基或卤代甲氧基的取代基取代;
R11、R12各自相互独立地选自氢、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6烷氧基烷基、C2-C6烯基、C2-C6卤代烯基、C2-C6炔基、C2-C6卤代炔基、C3-C8环烷基、C3-C8卤代环烷基、C1-C6烷氧基烷基、C1-C6卤代烷氧基烷基,和
苯基,其任选被一个或多个相互独立地选择的取代基R10取代;
R13、R14各自相互独立地选自氢、C1-C4烷基、C1-C6环烷基、C1-C4烷氧基烷基、苯基和苄基;
R15各自相互独立地选自氢、卤素、氰基、硝基、OH、SH、SCN、SF5、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,
C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个脂族和脂环族基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团;
苯基、苄基、吡啶基、苯氧基,其中后4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、(C1-C6烷氧基)羰基、(C1-C6烷基)氨基或二-(C1-C6烷基)氨基的取代基,
或者
存在于相同碳原子上的两个R15可一起为=O、=CH(C1-C4)、=C(C1-C4烷基)C1-C4烷基、=N(C1-C6烷基)或=NO(C1-C6烷基);
R16各自相互独立地选自氢、氰基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团,
苯基、苄基、吡啶基、苯氧基,其中后4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或(C1-C6烷氧基)羰基的取代基;
R17a、R17b各自相互独立地选自氢、氰基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基、C1-C6烷基亚硫酰基、C1-C6烷基磺酰基、C1-C6卤代烷硫基、三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基,
C1-C6烷基、C2-C6烯基、C2-C6炔基、C3-C8环烷基,其中最后提到的4个脂族和脂环族基团可以为未被取代的、部分或完全卤代和/或氧合的和/或可带有1或2个选自C1-C4烷氧基的基团,
苯基、苄基、吡啶基、苯氧基,其中最后提到的4个基团可以为未被取代的、部分或完全卤代的和/或带有1、2或3个选自C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或(C1-C6烷氧基)羰基的取代基,
或者
R17a和R17b可一起为C2-C6亚烷基链,与R17a和R17b所结合的氮原子一起形成3-7员饱和、部分饱和或不饱和环,其中亚烷基链可含有1或2个选自氧、硫或氮的杂原子,并可任选被卤素、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基取代,且其中杂环的氮和/或硫原子可任选被氧化;
n为相互独立地选自0、1或2的整数。
2.根据权利要求1的式(I)化合物,其中:
Het选自式Het-1、Het-11a和Het-24的基团:
其中#表示式(I)中的键,且其中:
R6a选自氢、卤素、C1-C4烷氧基或C1-C4烷基,其中后两个基团的碳原子可以为部分或完全卤代的;
k为0、1或2。
3.根据权利要求1的式(I)化合物,其中R1和R2都为氢。
4.根据权利要求1的式(I)化合物,其中:
R1为氢,且
R2为CH3。
5.根据权利要求1-4中任一项的式(I)化合物,其中:
R3a、R3b各自相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6卤代烷硫基、C1-C6烷硫基和OR8,其中R8为C(=O)R15,且R15为C1-C6烷基,其中脂族基团可以为未被取代的、部分或完全卤代的。
6.根据权利要求1-4中任一项的式(I)化合物,其中:
R3a、R3b各自相互独立地选自氢、氟、CN、C1-C6烷基和C1-C6卤代烷基。
7.根据权利要求1-4中任一项的式(I)化合物,其中:
R3a、R3b与它们所结合的碳原子一起形成环丙烷环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的。
8.根据权利要求1-4中任一项的式(I)化合物,其中p为0。
9.根据权利要求1-4中任一项的式(I)化合物,其中:
p为1,且
R4a、R4b相互独立地选自氢或卤素。
10.根据权利要求1-4中任一项的式(I)化合物,其中:
p为1,
且其中R4a或R4b中的一个可与相邻碳原子的R3a或R3b形成双键。
11.根据权利要求1-4中任一项的式(I)化合物,其中Y选自S、S=O或S(O)2。
12.根据权利要求1-4中任一项的式(I)化合物,其中Y为O。
13.根据权利要求1-4中任一项的式(I)化合物,其中:
R5选自氢、氰基、C1-C6烷基、C7-C10烷基、C3-C8环烷基,其中上述脂族和脂环族基团的碳链原子为未被取代的、部分或完全卤代的或者可带有一个或多个基团R7的任意组合,其中R7相互独立地选自卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基或C(=O)O-R16,
其中R16相互独立地为C1-C6烷基,其中烷基可以为未被取代的、部分或完全卤代的和/或可带有1或2个选自C1-C4烷氧基的取代基;
苯基或CH2-苯基、任选被1、2或3个取代基取代,所述取代基相互独立地选自氢、卤素、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基或苯氧基;
5-或6-员饱和、部分饱和或不饱和芳族杂环,所述芳族杂环选自吡啶、呋喃、唑、二唑、异唑、噻唑、噻二唑或异噻唑,其中杂环可直接结合在或经由CH2基团连接在分子的其余部分上,其中杂环为未被取代或者任选被1、2或3个相互独立地选择的取代基Ry取代,且其中:
Ry选自卤素、氰基和C1-C4烷基,其中烷基的碳原子可以为未被取代或者部分或完全卤代的和/或可带有1、2或3个选自C1-C4烷氧基的基团。
14.根据权利要求1-4中任一项的式(I)化合物,其中:
R5选自氢、氰基、C1-C6烷基、C3-C8环烷基,其中上述脂族基团各自为未被取代的、部分或完全卤代的。
15.根据权利要求1-4中任一项的式(I)化合物,其中:
R5选自C1-C4烷硫基、C3-C6环烷基硫基,其中上述脂族基团各自为未被取代的、部分或完全卤代的。
16.根据权利要求1-4中任一项的式(I)化合物,其中:
R5为苯基或CH2-苯基,其中芳环任选被1或2个取代基取代,所述取代基相互独立地选自氢、卤素、CN、C1-C4烷基、C1-C4烷氧基,其中最后提到的2个脂族基团都可以为未被取代或者部分或完全卤代的。
17.根据权利要求1-4中任一项的式(I)化合物,其中:
R5为选自如下的5-或6-员芳族杂环:
其中#表示与分子其余部分的键,且
其中键可以为单键或者经由CH2基团连接在分子的其余部分上;
其中:
Ry独立于q值且相互独立地选自氢、卤素、CN、C1-C4烷基和C1-C4烷氧基,其中最后提到的2个脂族基团都可以为未被取代的、部分或完全卤代的,
或者
相邻碳原子上的两个Ry可以为选自CH=CH-CH=CH或CH=CHCH2的桥,并因此与这两个Ry所结合的碳原子一起形成稠合的5员或6员芳族碳环,其中该环可任选被1或2个选自=O、OH、CH3、OCH3、卤素、氰基、卤代甲基或卤代甲氧基的取代基取代。
18.根据权利要求1-4中任一项的式(I)化合物,其中X为S。
19.根据权利要求1-4的式(I)化合物,其中X为O。
20.根据权利要求1的式(I)化合物:
其中:
W1、W2、W3和W4表示碳链基团,与N和C=N连接并并因此形成选自W.Het-1的饱和、不饱和或部分不饱和6员含氮杂环:
其中#表示与分子其余部分的键,
Rw6为氢;
且其中:
Het选自式Het-1、Het-11a和Het-24的基团:
其中#表示式(I)中的键,且其中:
R6a选自氢、卤素、C1-C4烷氧基或C1-C4烷基,其中后两个基团的碳原子可以为部分或完全卤代的;
k为0、1或2;
R1、R2相互独立地选自氢、C1-C3烷基;
X选自O或S;
且其中:
R3a、R3b相互独立地选自氢、卤素、CN、C1-C6烷基、C1-C6卤代烷基,或者其中:
R3a、R3b与它们所结合的碳原子一起形成环丙烷环,其中环的碳原子各自可以为未被取代的或者可以为部分或完全卤代的;
p为0;
Y为S(O)m,其中m为0、1或2;
且
R5选自氢、CN、C1-C6烷基、C1-C4烷硫基、C3-C6环烷基、C3-C6环烷基硫基,其中上述脂族和脂环族基团各自为未被取代的、部分或完全卤代的。
21.根据权利要求20的式(I)化合物,其中:
W1、W2、W3和W4表示碳链基团,与N和C=N连接并因此形成不饱和6员含氮杂环W.Het-1
其中#表示与分子其余部分的键,
Rw6为氢;
其中:
Het为Het-1或Het-11a:
其中#表示式(I)中的键,且其中:
R6a选自氢、卤素或C1-C4卤代烷基;
R1、R2都为氢;
X选自O或S,
且其中:
R3a、R3b相互独立地选自氢或氟;
p为0;
Y为S(O)m,其中m为0、1或2;且
R5为未被取代或者部分或完全卤代的C1-C3烷基。
22.用于对抗动物害虫的农用或兽用组合物,其包含至少一种如权利要求1-21中任一项所定义的化合物和至少一种惰性液体和/或固体可接受载体以及任选如果需要的话至少一种表面活性剂。
23.对抗或防治昆虫、蜘蛛或线虫组无脊椎害虫的方法,所述方法包括使所述害虫或其食物源、栖息地或繁殖地与杀虫有效量的至少一种如权利要求1-21中任一项所定义的化合物接触。
24.保护生长的植物以防昆虫、蜘蛛或线虫组无脊椎害虫侵袭或侵染的方法,所述方法包括使植物或者植物生长的土壤或水与杀虫有效量的至少一种如权利要求1-21中任一项所定义的化合物接触。
25.保护植物繁殖材料以防土壤昆虫以及保护秧苗根和芽以防土壤和叶面昆虫的方法,其包括使植物繁殖材料在播种以前和/或催芽以后与至少一种如权利要求1-21中任一项所定义的化合物接触。
26.根据权利要求25的方法,其中植物繁殖材料为种子。
27.如权利要求1-21中任一项所定义的化合物在制备用于处理受寄生虫侵袭或侵染的动物、防止动物受到寄生虫侵袭或侵染或者保护动物以防寄生虫侵袭或侵染的兽用组合物中的用途。
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CN104125774B (zh) | 2012-02-29 | 2016-09-28 | 明治制果药业株式会社 | 包括亚氨基吡啶衍生物的有害物防治组合物 |
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2014
- 2014-04-15 US US14/784,126 patent/US20160050923A1/en not_active Abandoned
- 2014-04-15 CN CN201480034839.5A patent/CN105324374B/zh not_active Expired - Fee Related
- 2014-04-15 EP EP14718046.7A patent/EP2986598B1/en not_active Not-in-force
- 2014-04-15 BR BR112015026357A patent/BR112015026357A2/pt not_active Application Discontinuation
- 2014-04-15 JP JP2016508126A patent/JP2016522173A/ja active Pending
- 2014-04-15 ES ES14718046.7T patent/ES2630373T3/es active Active
- 2014-04-15 WO PCT/EP2014/057573 patent/WO2014170300A1/en active Application Filing
- 2014-04-16 AR ARP140101636A patent/AR095895A1/es unknown
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US5250498A (en) * | 1989-12-14 | 1993-10-05 | Bayer Aktiengesellschaft | Herbicidal 2-iminopyridines |
EP0639569A1 (en) * | 1991-03-11 | 1995-02-22 | Nippon Soda Co., Ltd. | Novel heterocyclic compound |
CN102892290A (zh) * | 2010-08-31 | 2013-01-23 | 明治制果药业株式会社 | 有害生物防除剂 |
Also Published As
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CN105324374A (zh) | 2016-02-10 |
US20160050923A1 (en) | 2016-02-25 |
EP2986598B1 (en) | 2017-03-29 |
BR112015026357A2 (pt) | 2017-07-25 |
AR095895A1 (es) | 2015-11-18 |
EP2986598A1 (en) | 2016-02-24 |
WO2014170300A1 (en) | 2014-10-23 |
JP2016522173A (ja) | 2016-07-28 |
ES2630373T3 (es) | 2017-08-21 |
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