CN118103364A - 作为农药的新的吡嗪基-三唑化合物 - Google Patents
作为农药的新的吡嗪基-三唑化合物 Download PDFInfo
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- CN118103364A CN118103364A CN202280068781.0A CN202280068781A CN118103364A CN 118103364 A CN118103364 A CN 118103364A CN 202280068781 A CN202280068781 A CN 202280068781A CN 118103364 A CN118103364 A CN 118103364A
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- methyl
- ethyl
- triazol
- pyrazine
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- LQTPJFKKSLWSNB-UHFFFAOYSA-N 2-(2h-triazol-4-yl)pyrazine Chemical class C1=NNN=C1C1=CN=CC=N1 LQTPJFKKSLWSNB-UHFFFAOYSA-N 0.000 title abstract description 4
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- -1 chloro, bromo, iodo Chemical group 0.000 claims description 295
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 35
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
本发明涉及通式(I)的新型吡嗪基‑三唑化合物,其中结构元素X、R1、R2、R31、R31和R4具有说明书中给出的含义,涉及包含此类化合物的制剂和组合物,以及它们在植物保护中防治动物害虫(包括节肢动物和昆虫)中的用途以及它们在防治动物体外寄生虫中的用途。
Description
本发明涉及新的吡嗪基-三唑化合物、包含此类化合物的制剂和组合物,以及它们在植物保护中用于防治动物害虫(包括节肢动物和昆虫)的用途,以及它们用于防治动物体外寄生虫的用途。
在WO 2017/192385中公开了某些杂芳基-三唑化合物用于防治动物体外寄生虫的用途,在WO 2019/170626和WO 2019/215198中公开了其在植物保护领域中用于防治动物害虫(包括节肢动物和昆虫)的用途。此外,专利申请WO 2019/197468、WO 2019/201835、WO2019/202077、WO 2019/206799、WO 2021/013719、WO 2021/013720、WO 2021/069575、WO2021/069567、WO 2021/069569、WO 2021/099303、WO 2021/105091、WO 2021/165195、WO2021/224323和WO 2021/259997公开了某些杂芳基-三唑或杂芳基-吡嗪化合物用于防治动物体外寄生虫以及在植物保护领域中用于防治动物害虫(包括节肢动物和昆虫)的用途。WO2020/002563、WO 2020/053364、WO 2020/053365、WO 2020/070049、WO 2020/079198、WO2020/094363、WO 2020/169445、WO 2020/182649、WO 2020/188014、WO 2020/188027、WO2020/193341、WO 2020/201079、WO 2020/201398、WO 2020/208036、WO 2021/037614、WO2021/122645和WO2021/170881记载了所有可用作杀昆虫剂的唑-酰胺或吡嗪-酰胺化合物。
现代植物保护产品和兽用体外杀寄生虫剂必须满足许多要求,例如与功效、持久性、作用谱和抗性破坏特性相关的要求。毒性、与其他活性化合物或制剂助剂的相容性问题发挥着作用,以及合成活性化合物所需的费用问题也发挥着作用。此外,可能会出现抗性。由于所有这些原因,不能认为对新的作物保护组合物或兽用体外杀寄生虫剂的研究已经完成,而是持续需要与已知化合物相比至少在个别方面具有改进性质的新的化合物。
本发明的一个目的是提供在多个方面拓宽农药谱的化合物。
因此,本发明提供通式(I)的化合物
其中(构型1-1):
X为O或S;
R1为氢;
R2为选自以下的子结构Q1和Q2,其中连至C=X-基团的键用#标记:
其中
R21为卤素、-CN、-SF5、C1-C3卤代烷基、C1-C3卤代烷氧基、C1-C3卤代烷硫基、C1-C3卤代烷基亚磺酰基、C1-C3卤代烷基磺酰基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、C3-C4环烷硫基、C3-C4环烷基亚磺酰基、C3-C4环烷基磺酰基;或苯磺酰基,其中苯基任选地被一至两个选自卤素、-CN、甲基、三氟甲基和三氟甲氧基的取代基取代;或环丙基,其中环丙基任选地被一至两个选自卤素、-CN、甲基和三氟甲基的取代基取代;
R22为氢、卤素、-CN、C1-C3卤代烷基、C1-C3卤代烷氧基或C1-C3卤代烷基磺酰基;
R31为氢、C1-C3烷基或C3-C6环烷基;
R32为氢、C1-C3烷基或C3-C6环烷基,其中C1-C3烷基和C3-C6环烷基任选地被一至三个选自卤素、-CN、C3-C6环烷基和C1-C3烷氧基的取代基取代;
R4为氢、C1-C3烷基、C1-C3烷氧基或C3-C4环烷基。
本文任何位置记载的式(I)的化合物同样涵盖式(I)化合物的存在的任何非对映异构体或对映异构体和E/Z异构体,以及盐和N-氧化物,及其用于防治动物害虫的用途。
取决于取代基的性质,本文任何位置记载的式(I)化合物也可能是立体异构体的形式,即几何和/或旋光异构体或不同组成的异构体混合物的形式。本发明提供了纯立体异构体和这些异构体的任何所需混合物,尽管这里通常仅讨论式(I)的化合物。
然而,根据本发明优选使用式(I)化合物及其盐的光学活性、立体异构形式。
因此,本发明涉及纯对映异构体和非对映异构体及其混合物。
如果合适,式(I)化合物可以以各种多晶型形式或作为各种多晶型形式的混合物存在。纯多晶型物和多晶型物混合物均由本发明提供并且可以根据本发明使用。
优选式(I)的化合物(构型2-1),其中
X为O或S;
R1为氢;
R2选自以下子结构Q1和Q2,其中连接至C=X-基团的键用#标记:
其中
R21为氟、氯、溴、碘、-CN、环丙基、1-甲基环丙基、1-氰基环丙基、二氟甲基、1,1-二氟乙基、三氟甲基、氯二氟甲基、2-氟丙-2-基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、二氟甲基磺酰基、三氟甲基磺酰基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基磺酰基、环丙基磺酰基或4-氯苯基-磺酰基;
R22为氢、氟、氯、溴、碘、-CN、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、二氟甲基磺酰基或三氟甲基磺酰基;
R31为氢、甲基、乙基或环丙基;
R32为氢、C1-C3烷基或环丙基,其中C1-C3烷基和环丙基任选被1至3个选自氟、氯、-CN、环丙基和甲氧基的取代基取代;
R4为氢、甲基、环丙基或甲氧基。
还优选式(I)化合物(构型2-2),其中
X为O或S;
R1为氢;
R2选自以下子结构Q1和Q2,其中连接至C=X-基团的键用#标记:
其中
R21为氟、氯、溴、碘、-CN、-SF5、环丙基、1-甲基环丙基、1-氰基环丙基、二氟甲基、1,1-二氟乙基、三氟甲基、氯二氟甲基、2-氟丙-2-基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、二氟甲基磺酰基、三氟甲基磺酰基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基磺酰基、环丙基磺酰基或4-氯苯基-磺酰基;
R22为氢、氟、氯、溴、碘、-CN、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、1,1,2,2-四氟乙氧基、二氟甲基磺酰基或三氟甲基磺酰基;
R31为氢、甲基、乙基或环丙基;
R32为氢、C1-C3烷基或环丙基,其中C1-C3烷基和环丙基任选地被1至3个选自氟、氯、-CN、环丙基和甲氧基的取代基取代;
R4 R为氢、甲基、甲氧基或环丙基。
进一步优选式(I)化合物(构型3-1),其中
X为O;
R1为氢;
R2为3,5-双(三氟甲基)苯基、3,5-双(三氟甲氧基)苯基、3-环丙基-5-(三氟甲氧基)苯基、3-(1-甲基环丙基)-5-(三氟甲氧基)苯基、3-(1-氰基环丙基)-5-(三氟甲氧基)苯基、3-甲基磺酰基-5-(三氟甲基)苯基或3-甲基磺酰基-5-(三氟甲氧基)苯基;
R31为氢、甲基或乙基;
R32为氢、甲基、环丙基或环丙基甲基;
R4为氢、甲基或环丙基。
还进一步优选式(I)化合物(构型3-2),其中
X为O;
R1为氢;
R2为3-氯-5-(三氟甲基)苯基、3,5-双(二氟甲基)苯基、3,5-双(三氟甲基)苯基、3-溴-5-(2-氟丙-2-基)苯基、3-氟-5-(三氟甲氧基)苯基、3-溴-5-(三氟甲氧基)苯基、3,5-双(二氟甲氧基)苯基、3,5-双(三氟甲氧基)苯基、3-环丙基-5-(三氟甲氧基)苯基、3-(1-甲基环丙基)-5-(三氟甲氧基)苯基、3-(1-氰基环丙基)-5-(三氟甲氧基)苯基、3-氯-5-(五氟-λ6-硫烷基)苯基、3-溴-5-(五氟-λ6-硫烷基)苯基、3-氯-5-甲基磺酰基苯基、3-甲基磺酰基-5-(三氟甲基)苯基、3-甲基磺酰基-5-(三氟甲氧基)苯基、3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯基、3-(二氟甲基磺酰基)-5-(三氟甲氧基)苯基或2,6-双(二氟甲基)吡啶-4-基;
R31为氢、甲基或乙基;
R32为氢、甲基、氰基甲基、氰基乙基、2,2-二氟乙基、环丙基或环丙基甲基;
R4为氢、甲基、甲氧基或环丙基。
在另一个优选的实施方案中,本发明涉及式(I’)的化合物
其中结构元素R1、R2、R31、R32和R4具有构型(1-1)中给出的含义或构型(2-1)中给出的含义或构型(2-2)中给出的含或构型(3-1)中给出的含义或构型(3-2)中给出的含义。
在另一个优选的实施方案中,本发明涉及式(I”)的化合物,其中R1为氢并且
其中结构元素R1、R2、R31、R32和R4具有构型(1-1)中给出的含义或构型(2-1)中给出的含义或构型(2-2)中给出的含义或构型(3-1)中给出的含义或构型(3-2)中给出的含义。
在另一个优选的实施方案中,本发明涉及式(I”’)的化合物,其中R1为氢并且
其中结构元素R1、R2、R31、R32和R4具有构型(1-1)中给出的含义或构型(2-1)中给出的含义或构型(2-2)中给出的含义或构型(3-1)中给出的含义或构型(3-2)中给出的含义。
根据另一方面,本发明涵盖用于制备上述通式(I)化合物的中间体化合物。
特别地,本发明涵盖中间体化合物INT-001至INT-022(参见表2):
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(甲磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(3-甲基-5-{(1S)-1-[3-(甲磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(3-甲基-5-{(1S)-1-[3-(甲磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-[5-[(1S)-1-氨基乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺盐酸盐,
5-(5-{(1S)-1-[(叔丁氧基羰基)氨基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-{5-[(1S)-1-氨基乙基]-3-环丙基-1H-1,2,4-三唑-1-基}吡嗪-2-甲酸甲酯盐酸盐,
5-(3-环丙基-5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(二氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸。
定义
本领域技术人员应知晓,若无明确说明,本申请中使用的表述“一个”(“a”,“an”)可根据情况意指“一(1)个”、“一(1)或多个”或“至少一(1)个”。
对于本文所述的所有结构,例如环体系和基团,相邻的原子不得为-O-O-或-O-S-。
在本申请中,具有可变数目的可能碳原子(C原子)的结构可称为C碳原子的下限-C碳原子的上限结构(CLL-CUL结构),以便由此进行更具体的规定。实例:烷基可由3至10个碳原子组成,并且在这种情况下对应于C3-C10烷基。由碳原子和杂原子构成的环结构可称为“LL元至UL元”结构。6元环结构的一个实例为甲苯(被甲基取代的6元环结构)。
如果取代基的集合性术语(例如CLL-CUL烷基)位于复合取代基(例如,CLL-CUL环烷基-CLL-CUL烷基)的末端,则位于复合取代基的起始端的组分(例如,CLL-CUL环烷基)可以被在后取代基(例如,CLL-CUL-烷基)独立地且相同或不同地单取代或多取代。对于化学基团、环状体系和环状基团,在本申请中使用的所有集合性术语都可以通过附加词“CLL-CUL”或“LL元至UL元”进行更具体的规定。
在上述式中给出的符号的定义中,使用总体上代表以下取代基的集合性术语:
卤素是指第七主族的元素,优选氟、氯、溴和碘,更优选氟、氯和溴,且甚至更优选氟和氯。
杂原子的实例为N、O、S、P、B、Si。优选地,术语“杂原子”是指N、S和O。
根据本发明,“烷基”——其本身或作为化学基团的一部分——代表优选具有1至6个碳原子的直链烃或支链烃,例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、1,2-二甲基丙基、1,1-二甲基丙基、2,2-二甲基丙基、1-乙基丙基、己基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,2-二甲基丙基、1,3-二甲基丁基、1,4-二甲基丁基、2,3-二甲基丁基、1,1-二甲基丁基、2,2-二甲基丁基、3,3-二甲基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基丁基和2-乙基丁基。还优选具有1至4个碳原子的烷基,例如尤其是甲基、乙基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基或叔丁基。本发明的烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烯基”——其本身或作为化学基团的一部分——代表优选具有2至6个碳原子和至少一个双键的直链烃或支链烃,例如乙烯基、2-丙烯基、2-丁烯基、3-丁烯基、1-甲基-2-丙烯基、2-甲基-2-丙烯基、2-戊烯基、3-戊烯基、4-戊烯基、1-甲基-2-丁烯基、2-甲基-2-丁烯基、3-甲基-2-丁烯基、1-甲基-3-丁烯基、2-甲基-3-丁烯基、3-甲基-3-丁烯基、1,1-二甲基-2-丙烯基、1,2-二甲基-2-丙烯基、1-乙基-2-丙烯基、2-己烯基、3-己烯基、4-己烯基、5-己烯基、1-甲基-2-戊烯基、2-甲基-2-戊烯基、3-甲基-2-戊烯基、4-甲基-2-戊烯基、3-甲基-3-戊烯基、4-甲基-3-戊烯基、1-甲基-4-戊烯基、2-甲基-4-戊烯基、3-甲基-4-戊烯基、4-甲基-4-戊烯基、1,1-二甲基-2-丁烯基、1,1-二甲基-3-丁烯基、1,2-二甲基-2-丁烯基、1,2-二甲基-3-丁烯基、1,3-二甲基-2-丁烯基、2,2-二甲基-3-丁烯基、2,3-二甲基-2-丁烯基、2,3-二甲基-3-丁烯基、1-乙基-2-丁烯基、1-乙基-3-丁烯基、2-乙基-2-丁烯基、2-乙基-3-丁烯基、1,1,2-三甲基-2-丙烯基、1-乙基-1-甲基-2-丙烯基和1-乙基-2-甲基-2-丙烯基。还优选具有2至4个碳原子的烯基,例如尤其是2-丙烯基、2-丁烯基或1-甲基-2-丙烯基。本发明的烯基可以被一个或多个相同或不同的基团取代。
根据本发明,“炔基”——其本身或作为化学基团的一部分——代表优选具有2至6个碳原子和至少一个三键的直链烃或支链烃,例如2-丙炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-戊炔基、3-戊炔基、4-戊炔基、1-甲基-3-丁炔基、2-甲基-3-丁炔基、1-甲基-2-丁炔基、1,1-二甲基-2-丙炔基、1-乙基-2-丙炔基、2-己炔基、3-己炔基、4-己炔基、5-己炔基、1-甲基-2-戊炔基、1-甲基-3-戊炔基、1-甲基-4-戊炔基、2-甲基-3-戊炔基、2-甲基-4-戊炔基、3-甲基-4-戊炔基、4-甲基-2-戊炔基、1,1-二甲基-3-丁炔基、1,2-二甲基-3-丁炔基、2,2-二甲基-3-丁炔基、1-乙基-3-丁炔基、2-乙基-3-丁炔基、1-乙基-1-甲基-2-丙炔基和2,5-己二炔基。还优选具有2至4个碳原子的炔基,例如尤其是乙炔基、2-丙炔基或2-丁炔基-2-丙烯基。本发明的炔基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基”——其本身或作为化学基团的一部分——代表优选具有3至10个碳原子的单环烃、双环烃或三环烃,例如环丙基、环丁基、环戊基、环己基、环庚基、环辛基、双环[2.2.1]庚基、双环[2.2.2]辛基或金刚烷基。还优选具有3、4、5、6或7个碳原子的环烷基,例如尤其是环丙基或环丁基。本发明的环烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基环烷基”代表优选具有4至10个或4至7个碳原子的单环、双环或三环烷基环烷基,例如甲基环丙基、乙基环丙基、异丙基环丁基、3-甲基环戊基和4-甲基环己基。还优选具有4、5或7个碳原子的烷基环烷基,例如尤其是乙基环丙基或4-甲基环己基。本发明的烷基环烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基烷基”代表优选具有4至10个或4至7个碳原子的单环、双环或三环环烷基烷基,例如环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基和环戊基乙基。还优选具有4、5或7个碳原子的环烷基烷基,例如尤其是环丙基甲基或环丁基甲基。本发明的环烷基烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“羟烷基”代表优选具有1至6个碳原子的直链醇或支链醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇和叔丁醇。还优选具有1至4个碳原子的羟烷基。本发明的羟烷基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷氧基”代表优选具有1至6个碳原子的直链或支链O-烷基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基和叔丁氧基。还优选具有1至4个碳原子的烷氧基。本发明的烷氧基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷硫基(alkylthio)”或“烷基硫烷基(alkylsulfanyl)”代表优选具有1至6个碳原子的直链或支链S-烷基,例如甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基和叔丁硫基。还优选具有1至4个碳原子的烷硫基。本发明的烷硫基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基亚磺酰基”代表优选具有1至6个碳原子的直链或支链烷基亚磺酰基,例如甲基亚磺酰基、乙基亚磺酰基、正丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基和叔丁基亚磺酰基。还优选具有1至4个碳原子的烷基亚磺酰基。本发明的烷基亚磺酰基可以被一个或多个相同或不同的基团取代,并包括两种对映异构体。
根据本发明,“烷基磺酰基”代表优选具有1至6个碳原子的直链或支链烷基磺酰基,例如甲基磺酰基、乙基磺酰基、正丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基和叔丁基磺酰基。还优选具有1至4个碳原子的烷基磺酰基。本发明的烷基磺酰基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基硫基(cycloalkylthio)”或“环烷基硫烷基(cycloalkylsulfanyl)”代表优选具有3至6个碳原子的-S-环烷基,例如环丙硫基、环丁硫基、环戊硫基、环己硫基。还优选具有3至5个碳原子的环烷基硫基。本发明的环烷基硫基可以被一个或多个相同或不同的基团取代。
根据本发明,“环烷基亚磺酰基”代表优选具有3至6个碳原子的-S(O)-环烷基,例如环丙基亚磺酰基、环丁基亚磺酰基、环戊基亚磺酰基、环己基亚磺酰基。还优选具有3至5个碳原子的环烷基亚磺酰基。本发明的环烷基亚磺酰基可以被一个或多个相同或不同的基团取代,并包括两种对映异构体。
根据本发明,“环烷基磺酰基”代表优选具有3至6个碳原子的-SO2-环烷基,例如环丙基磺酰基、环丁基磺酰基、环戊基磺酰基、环己基磺酰基。还优选具有3至5个碳原子的环烷基磺酰基。本发明的环烷基磺酰基可以被一个或多个相同或不同的基团取代。
根据本发明,“苯硫基(phenylthio)”或“苯基硫烷基(phenylsulfanyl)”代表-S-苯基,例如苯硫基。本发明的苯硫基可以被一个或多个相同或不同的基团取代。
根据本发明,“苯基亚磺酰基”代表-S(O)-苯基,例如苯基亚磺酰基。本发明的苯基亚磺酰基可以被一个或多个相同或不同的基团取代,并包括两种对映异构体。
根据本发明,“苯基磺酰基”代表-SO2-苯基,例如苯基磺酰基。本发明的苯基磺酰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基羰基”代表优选具有2至7个碳原子的直链或支链烷基-C(=O),例如甲基羰基、乙基羰基、正丙基羰基、异丙基羰基、仲丁基羰基和叔丁基羰基。还优选具有1至4个碳原子的烷基羰基。本发明的烷基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷氧基羰基”——其单独或作为化学基团的组成部分——代表优选在烷氧基部分具有1至6个碳原子或具有1至4个碳原子的直链或支链烷氧基羰基,例如甲氧基羰基、乙氧基羰基、正丙氧基羰基、异丙氧基羰基、仲丁氧基羰基和叔丁氧基羰基。本发明的烷氧基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“烷基氨基羰基”代表优选在烷基部分具有1至6个碳原子或具有1至4个碳原子的直链或支链烷基氨基羰基,例如甲基氨基羰基、乙基氨基羰基、正丙基氨基羰基、异丙基氨基羰基、仲丁基氨基羰基和叔丁基氨基羰基。本发明的烷基氨基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“N,N-二烷基氨基羰基”代表优选在烷基部分具有1至6个碳原子或具有1至4个碳原子的直链或支链N,N-二烷基氨基羰基,例如N,N-二甲基氨基羰基、N,N-二乙基氨基羰基、N,N-二(正丙基氨基)羰基、N,N-二(异丙基氨基)羰基和N,N-二-(仲丁基氨基)羰基。本发明的N,N-二烷基氨基羰基可以被一个或多个相同或不同的基团取代。
根据本发明,“芳基”代表优选具有6至14个、特别是6至10个环碳原子的单环、双环或多环芳族体系,例如苯基、萘基、蒽基、菲基,优选苯基。此外,芳基还代表多环体系,如四氢萘基、茚基、茚满基、芴基、联苯基,其中键合位点在芳族体系上。本发明的芳基可以被一个或多个相同或不同的基团取代。
取代的芳基的实例为芳基烷基,其同样可以在C1-C4烷基和/或C6-C14芳基部分中被一个或多个相同或不同的基团取代。这种芳基烷基的实例包括苯甲基和苯基-1-乙基。
根据本发明,术语“多环”环是指稠合的、桥接的和螺环的碳环和杂环以及通过单键或双键连接的环体系。
根据本发明,“杂环”、“杂环族环”或“杂环体系”代表具有至少一个环的碳环体系,所述环中至少一个碳原子被杂原子替代,优选被选自N、O、S、P、B、Si、Se的杂原子替代,并且其为饱和的、不饱和的或杂芳族的,并且可以是未取代的或取代的,其中键合位点在环原子上。除非另有不同定义,杂环包含优选3至9个环原子,尤其是3至6个环原子,并且杂环中的一个或多个、优选1至4个、尤其是1个、2个或3个杂原子优选选自N、O和S,但是两个氧原子不应直接相邻。杂环通常含有不超过4个氮原子和/或不超过2个氧原子和/或不超过2个硫原子。在任选地取代的杂环基的情况下,本发明还包括多环环体系,例如8-氮杂双环[3.2.1]辛基、1-氮杂双环[2.2.1]庚基、1-氧杂-5-氮杂螺[2.3]己基或2,3-二氢-1H-吲哚。
本发明的杂环基为例如:哌啶基、哌嗪基、吗啉基、硫代吗啉基、二氢吡喃基、四氢吡喃基、二氧杂环己烷基(dioxanyl)、吡咯啉基、吡咯烷基、咪唑啉基、咪唑烷基、噻唑烷基、噁唑烷基、二氧戊环基、二氧杂环戊烯基(dioxolyl)、吡唑烷基、四氢呋喃基、二氢呋喃基、氧杂环丁烷基(oxetanyl)、氧杂环丙烷基(oxiranyl)、氮杂环丁烷基(azetidinyl)、氮杂环丙烷基(aziridinyl)、氧氮杂环丁烷基(oxazetidinyl)、氧氮杂环丙烷基(oxaziridinyl)、氧氮杂环庚烷基(oxazepanyl)、氧氮杂环己烷基(oxazinanyl)、氮杂环庚烷基(azepanyl)、氧代吡咯烷基、二氧代吡咯烷基、氧代吗啉基、氧代哌嗪基和氧杂环庚烷基(oxepanyl)。
特别重要的是杂芳基,即杂芳族体系。根据本发明,术语“杂芳基”代表杂芳族化合物,即落入上述杂环定义下的完全不饱和的芳族杂环化合物。优选选自上述的具有1至3个、优选1或2个相同或不同的杂原子的5至7元环。本发明的杂芳基为例如:呋喃基、噻吩基、吡唑基、咪唑基、1,2,3-三唑基和1,2,4-三唑基、异噁唑基、噻唑基、异噻唑基、1,2,3-噁二唑基、1,3,4-噁二唑基、1,2,4-噁二唑基和1,2,5-噁二唑基、氮杂环庚三烯基(azepinyl)、吡咯基、吡啶基、哒嗪基、嘧啶基、吡嗪基、1,3,5-三嗪基、1,2,4-三嗪基和1,2,3-三嗪基、1,2,4-噁嗪基、1,3,2-噁嗪基、1,3,6-噁嗪基和1,2,6-噁嗪基、氧杂环庚三烯基(oxepinyl)、硫杂环庚三烯基(thiepinyl)、1,2,4-三唑酮基(1,2,4-triazolonyl)和1,2,4-二氮杂环庚三烯基(1,2,4-diazepinyl)。本发明的杂芳基还可以被一个或多个相同或不同的基团取代。
根据本发明,取代基=O(氧代)可以替代亚甲基(CH2)基团的两个氢原子或仅带有氢以外的取代基的硫、氮和磷原子的孤对电子。例如,基团C2-烷基通过被=O(氧代)取代而变为例如-COCH3,而杂环硫杂环丁-3-基-通过被一个=O(氧代)取代而变为例如1-氧代硫杂环丁-3-基,或被两个=O(氧代)基团取代而变为1,1-二氧代硫杂环丁-3-基。
根据本发明,取代基=S(硫酮(thiono))可以替代亚甲基(CH2)基团的两个氢原子。例如,基团C2-烷基通过被=S(硫酮)取代而变为例如-CSCH3。
如本文所用,术语“任选地取代的”意指任选地取代的基团或者被另外的取代基取代或者不被另外的取代基取代。
术语“在各自情况下任选地取代的”意指基团/取代基——例如烷基、烯基、炔基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、环烷基、芳基、苯基、苯甲基、杂环基和杂芳基——被取代,意指,例如由未取代的基础结构衍生出的取代的基团,其中取代基,例如一个(1)取代基或多个取代基,优选1、2、3、4、5、6或7个取代基选自:氨基、羟基、卤素、硝基、氰基、异氰基、巯基、异硫氰酸酯基、C1-C4羧基、碳酰胺基、SF5、氨基磺酰基、C1-C4烷基、C1-C4卤代烷基、C3-C4环烷基、C2-C4烯基、C5-C6环烯基、C2-C4炔基、N-单-C1-C4烷基氨基、N,N-二-C1-C4烷基氨基、N-C1-C4烷酰基氨基、C1-C4烷氧基、C1-C4卤代烷氧基、C2-C4烯氧基、C2-C4炔氧基、C3-C4环烷氧基、C5-C6环烯氧基、C1-C4烷氧基羰基、C2-C4烯氧基羰基、C2-C4炔氧基羰基、C6-芳氧基羰基、C10-芳氧基羰基、C14-芳氧基羰基、C1-C4烷酰基、C2-C4烯基羰基、C2-C4炔基羰基、C6-芳基羰基、C10-芳基羰基、C14-芳基羰基、C1-C4烷硫基、C1-C4卤代烷硫基、C3-C4环烷基硫基、C2-C4烯硫基、C5-C6环烯基硫基、C2-C4炔硫基、C1-C4烷基亚磺酰基(包括C1-C4烷基亚磺酰基的两种对映异构体)、C1-C4卤代烷基亚磺酰基(包括C1-C4卤代烷基亚磺酰基的两种对映异构体)、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、N-单-C1-C4烷基氨基磺酰基、N,N-二-C1-C4烷基氨基磺酰基、C1-C4烷基亚膦酰基、C1-C4烷基膦酰基(包括C1-C4烷基亚膦酰基和C1-C4烷基膦酰基的两种对映异构体)、N-C1-C4烷基氨基羰基、N,N-二-C1-C4烷基氨基羰基、N-C1-C4烷酰基氨基羰基、N-C1-C4烷酰基-N-C1-C4烷基氨基羰基、C6-芳基、C10-芳基、C14-芳基、C6-芳氧基、C10-芳氧基、C14-芳氧基、苯甲基、苯甲氧基、苯甲硫基、C6-芳硫基、C10-芳硫基、C14-芳硫基、C6-芳氨基、C10-芳氨基、C14-芳氨基、苯甲氨基、杂环基和三烷基甲硅烷基,通过双键键合的取代基,如C1-C4-亚烷基(例如亚甲基或亚乙基)、氧代基团、亚氨基和取代的亚氨基。当两个或更多个基团形成一个或多个环时,这些环可以是碳环、杂环、饱和的、部分饱和的、不饱和的,例如包括芳族环和具有进一步的取代。以举例方式提及的取代基(“第一取代基级别”)——如果它们包含含烃部分——可任选地在其中具有进一步的取代(“第二取代基级别”),例如被一个或多个各自独立地选自以下的取代基取代:卤素、羟基、氨基、硝基、氰基、异氰基、叠氮基、酰胺基、氧代基团和亚氨基。术语“(任选)取代的”基团优选仅包括一个或两个取代基级别。
本发明的卤素取代的化学基团或卤代基团(例如,烷基或烷氧基)被卤素单取代或多取代,最多至最大可能的取代基数目。这类基团也称为卤代基团(例如,卤代烷基)。在被卤素多取代的情况下,卤素原子可以是相同或不同的,并且可以全部键合到一个碳原子上或可以键合到多个碳原子上。卤素特别为氟、氯、溴或碘,优选氟、氯或溴并且更优选氟。更具体而言,卤素取代的基团是单卤代环烷基,如1-氟环丙基、2-氟环丙基或1-氟环丁基;单卤代烷基,如2-氯乙基、2-氟乙基、1-氯乙基、1-氟乙基、氯甲基或氟甲基;全卤代烷基,如三氯甲基或三氟甲基或CF2CF3;多卤代烷基,如二氟甲基、2-氟-2-氯乙基、二氯甲基、1,1,2,2-四氟乙基或2,2,2-三氟乙基。卤代烷基的其他实例为三氯甲基、氯二氟甲基、二氯氟甲基、氯甲基、溴甲基、1-氟乙基、2-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2,2,2-三氯乙基、2-氯-2,2-二氟乙基、五氟乙基、3,3,3-三氟丙基和五氟叔丁基。优选这样的卤代烷基:其具有1至4个碳原子和1至9个、优选1至5个相同或不同的选自氟、氯和溴的卤素原子。特别优选具有1或2个碳原子和1至5个相同或不同的选自氟和氯的卤素原子的卤代烷基,例如尤其是二氟甲基、三氟甲基或2,2-二氟乙基。卤素取代的化合物的其他实例为卤代烷氧基,如OCF3、OCHF2、OCH2F、OCF2CF3、OCH2CF3、OCH2CHF2和OCH2CH2Cl;卤代烷基硫烷基,如二氟甲硫基、三氟甲硫基、三氯甲硫基、氯二氟甲硫基、1-氟乙硫基、2-氟乙硫基、2,2-二氟乙硫基、1,1,2-四氟乙硫基、2,2,2-三氟乙硫基或2-氯-1,1,2-三氟乙硫基;卤代烷基亚磺酰基,如二氟甲基亚磺酰基、三氟甲基亚磺酰基、三氯甲基亚磺酰基、氯二氟甲基亚磺酰基、1-氟乙基亚磺酰基、2-氟乙基亚磺酰基、2,2-二氟乙基亚磺酰基、1,1,2,2-四氟乙基亚磺酰基、2,2,2-三氟乙基亚磺酰基和2-氯-1,1,2-三氟乙基亚磺酰基;卤代烷基亚磺酰基,如二氟甲基亚磺酰基、三氟甲基亚磺酰基、三氯甲基亚磺酰基、氯二氟甲基亚磺酰基、1-氟乙基亚磺酰基、2-氟乙基亚磺酰基、2,2-二氟乙基亚磺酰基、1,1,2,2-四氟乙基亚磺酰基、2,2,2-三氟乙基亚磺酰基和2-氯-1,1,2-三氟乙基亚磺酰基;卤代烷基磺酰基,如二氟甲基磺酰基、三氟甲基磺酰基、三氯甲基磺酰基、氯二氟甲基磺酰基、1-氟乙基磺酰基、2-氟乙基磺酰基、2,2-二氟乙基磺酰基、1,1,2,2-四氟乙基磺酰基、2,2,2-三氟乙基磺酰基和2-氯-1,1,2-三氟乙基磺酰基。
在具有碳原子的基团的情况下,优选具有1至4个碳原子,特别是1或2个碳原子的那些基团。通常优选选自以下的取代基:卤素,例如氟和氯;(C1-C4)烷基,优选甲基或乙基;(C1-C4)卤代烷基,优选三氟甲基;(C1-C4)烷氧基,优选甲氧基或乙氧基;(C1-C4)卤代烷氧基;硝基和氰基。本文特别优选以下取代基:甲基、甲氧基、氟和氯。
取代的氨基,例如单取代或二取代的氨基,意指选自以下的取代的氨基基团,即所述氨基例如被一个或两个相同或不同的选自以下的基团N-取代:烷基、羟基、氨基、烷氧基、酰基和芳基;优选N-单烷基氨基和N,N-二烷基氨基(如甲基氨基、乙基氨基、N,N-二甲基氨基、N,N-二乙基氨基、N,N-二正丙基氨基、N,N-二异丙基氨基或N,N-二丁基氨基),N-单烷氧基烷基氨基或N,N-二烷氧基烷基氨基基团(如N-甲氧基甲基氨基、N-甲氧基乙基氨基、N,N-二(甲氧基甲基)氨基或N,N-二(甲氧基乙基)氨基),N-单芳基氨基和N,N-二芳基氨基,如任选取代的苯胺、酰基氨基、N,N-二酰基氨基、N-烷基-N-芳基氨基、N-烷基-N-酰基氨基以及饱和的N-杂环;本文优选具有1至4个碳原子的烷基基团;在本文中,芳基优选为苯基或取代的苯基;对于酰基,适用下文进一步给出的定义,优选(C1-C4)烷酰基。这同样适用于取代的羟氨基或肼基。
取代的氨基还包括在氮原子上具有四个有机取代基的季铵化合物(盐)。
任选地取代的苯基优选为未取代的或被相同或不同的选自以下的基团单取代或多取代、优选最高达三取代的苯基,所述基团选自:卤素、(C1-C4)烷基、(C1-C4)烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷基、(C1-C4)卤代烷氧基、(C1-C4)烷硫基、(C1-C4)卤代烷硫基、(C1-C4)烷基亚磺酰基、(C1-C4)卤代烷基亚磺酰基、(C1-C4)烷基磺酰基、(C1-C4)卤代烷基磺酰基、氰基、异氰基和硝基,例如邻甲苯基、间甲苯基和对甲苯基、二甲基苯基、2-氯苯基、3-氯苯基和4-氯苯基、2-氟苯基、3-氟苯基和4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基和4-三氟甲基苯基和4-三氯甲基苯基、2,4-二氯苯基、3,5-二氯苯基、2,5-二氯苯基和2,3-二氯苯基、邻甲氧基苯基、间甲氧基苯基和对甲氧基苯基、4-七氟苯基。
任选地取代的环烷基优选为未取代的或被相同或不同的选自以下的基团单取代或多取代、优选最高达三取代的环烷基,所述基团选自:卤素、氰基、(C1-C4)烷基、(C1-C4)烷氧基、(C1-C4)烷氧基-(C1-C4)烷氧基、(C1-C4)烷氧基-(C1-C4)烷基、(C1-C4)卤代烷基和(C1-C4)卤代烷氧基,尤其是被1个或2个(C1-C4)烷基基团取代。
本发明的化合物可以以优选的实施方案存在。本文中所述的各个实施方案可以彼此组合。不包括违反自然规律的组合以及本领域技术人员会基于他/她的专业知识由此排除的组合。例如,排除具有三个或更多个相邻氧原子的环结构。
异构体
根据取代基的性质,式(I)的化合物可为几何异构体和/或光学活性异构体或相应的具有不同组成的异构体混合物的形式。这些立体异构体为例如对映异构体、非对映异构体、阻转异构体或几何异构体。因此,本发明包括纯的立体异构体和任何这些异构体的混合物。
同位素变体
本发明还涵盖式(I)化合物所有合适的同位素变体。此类化合物的同位素变体被理解为意指至少一个原子被同一原子序数但原子质量与自然界中通常或主要存在的原子质量不同的另一个原子替换的式(I)的化合物。纳入式(I)化合物的同位素实例为氢、碳、氮、氧、磷、硫、氟、氯、溴和碘的同位素,如2H(氘)、3H(氚)、13C、14C、15N、17O、18O、32P、33P、33S、34S、35S、36S、18F、36Cl、82Br、123I、124I、129I和131I。式(I)化合物的特定同位素变体,特别是含有一个或多个放射性同位素的变体,可有益于比如研究作用机制或体内活性成分的分布;由于比较容易制备和检测,特别是用3H或14C同位素标记的化合物适用于此目的。此外,掺入同位素(例如氘),由于化合物的代谢稳定性增强,可带来好处,例如延长半衰期或减少所需的有效剂量。因此,式(I)化合物的同位素修饰也可以构成本发明的优选实施方案。式(I)化合物的同位素变体可以通过本领域技术人员已知的方法制备,例如通过下文描述的方法和实施例中给出的说明,通过对相应的试剂和/或起始化合物进行合适的同位素修饰而进行。
方法和用途
本发明还涉及防治动物害虫的方法,其中将式(I)的化合物作用于动物害虫和/或其生境。动物害虫的防治优选在农业和林业中、以及在材料保护中进行。由此优选排除对人体或动物体的手术方法或治疗方法以及在人体或动物体上实施的诊断方法。
本发明还涉及式(I)的化合物作为农药的用途,尤其是作为作物保护剂的用途。
在本申请的上下文中,术语“农药”在每种情况下还总是包括术语“作物保护剂”。
式(I)的化合物由于具有良好的植物耐受性、有利的恒温动物毒性和良好的环境相容性而适用于下述用途:保护植物和植物器官抵抗生物和非生物胁迫因素、提高采收产量、改善采收物的品质以及防治在农业、园艺、畜牧业、水产养殖业、林业、园林和休闲设施、储存产品和材料的保护以及卫生领域中遇到的动物害虫,尤其是昆虫、蛛形纲动物、蠕虫,尤其是线虫和软体动物。
在本专利申请的上下文中,术语“卫生”理解为意指旨在预防疾病、特别是感染性疾病以及用于保护人类和动物健康和/或保护环境和/或保持清洁的任何和所有措施、方法和实践。根据本发明,这尤其包括对例如纺织品或硬质表面,特别是玻璃、木材、混凝土、瓷器、陶瓷、塑料或金属表面进行清洁、消毒和杀菌,以及确保它们免于卫生害虫和/或其分泌物的措施。在这方面,本发明的范围优选排除可施用于人体或动物体的手术或治疗性的方法以及在人体或动物体上实施的诊断方法。
因此,术语“卫生领域”包括这些卫生措施、方法和实践对其很重要的所有区域、技术领域和工业应用,例如在厨房、面包房、机场、浴室、游泳池、百货商店、酒店、医院、马厩、动物饲养等中的卫生。
因此,术语“卫生害虫”理解为意指一种或多种这样的动物害虫:其在卫生领域中的存在是成问题的,特别是出于健康原因。因此,主要目的是避免在卫生领域中存在卫生害虫和/或避免暴露于这些卫生害虫,或使其最小化。这尤其可以通过施加既可以用于预防感染也可以用于处理已存在的感染的农药来实现。还可以使用避免或减少暴露于害虫的制剂。例如,卫生害虫包括下文提及的生物体。
因此,术语“卫生保护”涵盖用于维持和/或改善这些卫生措施、方法和实践的所有行为。
式(I)的化合物可优选用作农药。它们对于通常敏感性和抗性的物种以及对于发育的所有或某些阶段均具有活性。上述害虫包括:
节肢动物门(Arthropoda)、尤其是蛛形纲(Arachnida)的害虫,例如粉螨属(Acarus spp.)(例如粗脚粉螨(Acarus siro)、枸杞瘤瘿螨(Aceria kuko)、柑橘瘤瘿螨(Aceria sheldoni))、刺皮瘿螨属(Aculops spp.)、针刺瘿螨属(Aculus spp.)(例如佛氏刺瘿螨(Aculus fockeui)、苹果刺瘿螨(Aculus schlechtendali))、花蜱属(Amblyommaspp.)、山楂叶螨(Amphitetranychus viennensis)、锐缘蜱属(Argas spp.)、牛蜱属(Boophilus spp.)、短须螨属(Brevipalpus spp.)(例如紫红短须螨(Brevipalpusphoenicis))、蚜苔螨(Bryobia graminum)、苜蓿苔螨(Bryobia praetiosa)、刺尾蝎属(Centruroides spp.)、皮螨属(Chorioptes spp.)、鸡皮刺螨(Dermanyssus gallinae)、欧洲屋尘螨(Dermatophagoides pteronyssinus)、美洲屋尘螨(Dermatophagoidesfarinae)、革蜱属(Dermacentor spp.)、始叶螨属(Eotetranychus spp.)(例如核桃始叶螨(Eotetranychus hicoriae))、梨上瘿螨(Epitrimerus pyri)、真叶螨属(Eutetranychusspp.)(例如班氏真叶螨(Eutetranychus banksi))、瘿螨属(Eriophyes spp.)(例如梨瘿螨(Eriophyes pyri))、家甜食螨(Glycyphagus domesticus)、红足海镰螯螨(Halotydeusdestructor)、半跗线螨属(Hemitarsonemus spp.)(例如茶半跗线螨(Hemitarsonemuslatus)(=侧多食跗线螨(Polyphagotarsonemus latus)))、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、毒蛛属(Latrodectus spp.)、斜蛛属(Loxosceles spp.)、秋收恙螨(Neutrombicula autumnalis)、Nuphersa属、小爪螨属(Oligonychus spp.)(例如跗线螨(Oligonychus coffeae)、Oligonychus coniferarum、冬青小爪螨(Oligonychus ilicis)、甘蔗小爪螨(Oligonychus indicus)、芒果小爪螨(Oligonychus mangiferus)、草地小爪螨(Oligonychus pratensis)、石榴小爪螨(Oligonychus punicae)、樟小爪螨(Oligonychusyothersi))、钝缘蜱属(Ornithodorus spp)、禽刺螨属(Ornithonyssus spp.)、全爪螨属(Panonychus spp.)(例如柑桔全爪螨(Panonychus citri(=Metatetranychus citri))、苹果全爪螨(Panonychus ulmi(=Metatetranychus ulmi)))、柑桔锈螨(Phyllocoptrutaoleivora)、多趾宽叶螨(Platytetranychus multidigituli)、侧多食跗线螨(Polyphagotarsonemus latus)、痒螨属(Psoroptes spp.)、扇头蜱属(Rhipicephalusspp.)、根螨属(Rhizoglyphus spp.)、疥螨属(Sarcoptes spp.)、中东金蝎(Scorpiomaurus)、狭跗线螨种(Stenotarsonemus spp.)、稻细螨(Steneotarsonemus spinki)、跗线螨属(Tarsonemus spp.)(例如乱跗线螨(Tarsonemus confusus)、樱草狭跗线螨(Tarsonemus pallidus))、叶螨属(Tetranychus spp.)(例如加拿大叶螨(Tetranychuscanadensis)、朱砂叶螨(Tetranychus cinnabarinus)、土耳其斯坦叶螨(Tetranychusturkestani)、二斑叶螨(Tetranychus urticae))、阿氏真恙螨(Trombiculaalfreddugesi)、Vaejovis属、番茄斜背瘤瘿螨(Vasates lycopersici);
唇足纲(Chilopoda)的害虫,例如,地蜈蚣属(Geophilus spp.)、蚰蜓属(Scutigera spp.);
弹尾目或弹尾纲(Collembola)的害虫,例如,武装棘跳虫(Onychiurus armatus);绿圆跳虫(Sminthurus viridis);
倍足纲(Diplopoda)的害虫,例如,千足虫(Blaniulus guttulatus);
昆虫纲(Insecta)的害虫,例如蜚蠊目(Blattodea),如东方蜚蠊(Blattaorientalis)、亚洲蜚蠊(Blattella asahinai)、德国小蠊(Blattella germanica)、马德拉蜚蠊(Leucophaea maderae)、Loboptera decipiens、家屋斑蠊(Neostylopygarhombifolia)、古巴蠊属(Panchlora spp.)、木蠊属(Parcoblatta spp.)、大蠊属(Periplaneta spp.)(例如美洲大蠊(Periplaneta americana)、澳洲大蠊(Periplanetaaustralasiae))、蔗蠊(Pycnoscelus surinamensis)、棕带蜚蠊(Supella longipalpa);
鞘翅目(Coleoptera)的害虫,例如,条纹南瓜甲(Acalymma vittatum)、菜豆象(Acanthoscelides obtectus)、喙丽金龟属(Adoretus spp.)、小蜂窝甲虫(Aethinatumida)、杨树萤叶甲(Agelastica alni)、长吉丁属(Agrilus spp.),例如(白蜡窄吉丁(Agrilus planipennis)、Agrilus coxalis、Agrilus bilineatus、Agrilus anxius)、叩甲属(Agriotes spp.)(例如直条叩头虫(Agriotes linneatus)、小麦叩头虫(Agriotesmancus))、Agriotes obscurus、黑菌虫(Alphitobius diaperinus)、马铃薯鳃角金龟(Amphimallon solstitialis)、家具窃蠹(Anobium punctatum)、Anomala dubia、星天牛属(Anoplophora spp.)(例如光肩星天牛(Anoplophora glabripennis))、花象属(Anthonomus spp.)(例如棉铃象甲(Anthonomus grandis))、圆皮蠹属(Anthrenus spp.)、梨象属(Apion spp.)、阿鳃金龟属(Apogonia spp.)、Athous haemorrhoidales、隐食甲属(Atomaria spp.)(例如甜菜隐食甲(Atomaria linearis))、毛皮蠹属(Attagenus spp.)、Baris caerulescens、噁条豆象(Bruchidius obtectus)、豆象属(Bruchus spp.)(例如豌豆象(Bruchus pisorum)、蚕豆象(Bruchus rufimanus))、龟叶甲属(Cassida spp.)、菜豆莹叶甲(Cerotoma trifurcata)、龟象属(Ceuthorhynchus spp.)(例如白菜籽龟象(Ceutorrhynchus assimilis)、甘蓝茎龟象(Ceutorrhynchus quadridens)、白菜龟象(Ceutorrhynchus rapae))、跳甲属(Chaetocnema spp.)(例如甘薯跳甲(Chaetocnemaconfinis)、美国齿跳甲(Chaetocnema denticulata)、荒地玉米跳甲(Chaetocnemaectypa))、Cleonus mendicus、宽胸叩头虫属(Conoderus spp.)、根颈象属(Cosmopolitesspp.)(例如香蕉根颈象甲(Cosmopolites sordidus))、褐新西兰肋翅鳃角金龟(Costelytra zealandica)、叩甲属(Ctenicera spp.)、象虫属(Curculio spp.)(例如美核桃象(Curculio caryae)、大栗象(Curculio caryatrypes)、美洲榛子象(Curculioobtusus)、小栗象(Curculio sayi))、锈赤扁谷盗(Cryptolestes ferrugineus)、长角扁谷盗(Cryptolestes pusillus)、杨干隐喙(Cryptorhynchus lapathi)、芒果果核象甲(Cryptorhynchus mangiferae)、细枝象属(Cylindrocopturus spp.)、密点细枝象(Cylindrocopturus adspersus)、洋松细枝象(Cylindrocopturus furnissi)、大小蠹属(Dendroctonus spp.)(例如中欧山松大小蠹(Dendroctonus ponderosae))、皮蠹属(Dermestes spp.)、叶甲属(Diabrotica spp.)(例如带斑黄瓜条叶甲(Diabroticabalteata)、北方玉米根叶甲(Diabrotica barberi)、南方十一星瓜叶甲(Diabroticaundecimpunctata howardi)、南方十一星瓜叶甲亚种(Diabrotica undecimpunctataundecimpunctata)、西方玉米根叶甲(Diabrotica virgifera virgifera)、墨西哥玉米根叶甲(Diabrotica virgifera zeae))、蛀野螟属(Dichocrocis spp.)、水稻铁甲(Dicladispa armigera)、Diloboderus属、Epicaerus属、食植瓢虫属(Epilachna spp.)(例如瓜食植瓢虫(Epilachna borealis)、墨西哥豆瓢虫(Epilachna varivestis))、毛跳甲属(Epitrix spp.)(例如黄瓜跳甲(Epitrix cucumeris)、茄子跳甲(Epitrix fuscula)、烟草跳甲(Epitrix hirtipennis)、美国马铃薯跳甲(Epitrix subcrinita)、块茎跳甲(Epitrixtuberis))、钻孔虫属(Faustinus spp.)、裸蛛甲(Gibbium psylloides)、阔角谷盗(Gnathocerus cornutus)、菜心野螟(Hellula undalis)、黑异爪蔗金龟(Heteronychusarator)、寡节鳃金龟属(Heteronyx spp.)、Hoplia argentea、Hylamorpha elegans、北美家天牛(Hylotrupes bajulus)、紫苜蓿叶象(Hypera postica)、蓝绿象(Hypomecessquamosus)、咪小蠹属(Hypothenemus spp.)(例如咖啡果小蠹(Hypothenemus hampei)、苹枝小囊(Hypothenemus obscurus)、毛竹小蠹(Hypothenemus pubescens))、甘蔗大褐齿爪鳃金龟(Lachnosterna consanguinea)、烟草甲(Lasioderma serricorne)、长头谷盗(Latheticus oryzae)、波缘薪甲属(Lathridius spp.)、负泥虫属(Lema spp.)、马铃薯甲虫(Leptinotarsa decemlineata)、潜叶蛾属(Leucoptera spp.)(例如咖啡潜叶蛾(Leucoptera coffeella))、Limonius ectypus、稻根象(Lissorhoptrus oryzophilus)、Listronotus(=Hyperodes)属、筒喙象属(Lixus spp.)、Luperodes属、黄胸寡毛跳甲(Luperomorpha xanthodera)、粉蠹属(Lyctus spp.)、Megacyllene属(例如Megacyllenerobiniae)、美洲叶甲属(Megascelis spp.)、梳爪叩头虫属(Melanotus spp.)(例如Melanotus longulus oregonensis)、油菜花露尾甲(Meligethes aeneus)、鳃金龟属(Melolontha spp.)(例如欧洲鳃金龟(Melolontha melolontha))、Migdolus属、墨天牛属(Monochamus spp.)、象甲(Naupactus xanthographus)、隐跗郭公虫属(Necrobia spp.)、Neogalerucella属、黄蛛甲(Niptus hololeucus)、椰蛀犀金龟(Oryctes rhinoceros)、锯谷盗(Oryzaephilus surinamensis)、Oryzaphagus oryzae、耳喙象属(Otiorrhynchusspp.)(例如苹果耳喙象(Otiorhynchus cribricollis)、苜蓿耳喙象(Otiorhynchusligustici)、草莓耳喙象(Otiorhynchus ovatus)、粗糙草莓耳喙象(Otiorhynchusrugosostriarus)、黑葡萄耳喙象(Otiorhynchus sulcatus))、负泥虫属(Oulema spp.)(例如橙足负泥虫(Oulema melanopus)、稻负泥虫(Oulema oryzae))、小青花金龟(Oxycetoniajucunda)、辣根猿叶虫(Phaedon cochleariae)、食叶鳃金龟属(Phyllophaga spp.)、鳃金龟(Phyllophaga helleri)、黄条跳甲属(Phyllotreta spp.)(例如辣根条跳甲(Phyllotreta armoraciae)、西方黑跳甲(Phyllotreta pusilla)、美条纹跳甲(Phyllotreta ramosa)、黄曲条跳甲(Phyllotreta striolata))、日本弧丽金龟(Popilliajaponica)、象甲属(Premnotrypes spp.)、大谷蠹(Prostephanus truncatus)、跳甲属(Psylliodes spp.)(例如马铃薯跳甲(Psylliodes affinis)、油菜兰跳甲(Psylliodeschrysocephala)、忽布跳甲(Psylliodes punctulata))、蛛甲属(Ptinus spp.)、暗色瓢虫(Rhizobius ventralis)、谷蠹(Rhizopertha dominica)、隐喙象属(Rhynchophorusspp.)、红棕象甲(Rhynchophorus ferrugineus)、棕榈象甲(Rhynchophorus palmarum)、小蠹属(Scolytus spp.)(例如欧洲榆小蠹(Scolytus multistriatus))、Sinoxylonperforans、谷象属(Sitophilus spp.)(例如谷象(Sitophilus granarius)、罗望子象(Sitophilus linearis)、米象(Sitophilus oryzae)、玉米象(Sitophilus zeamais))、尖隐喙象属(Sphenophorus spp.)、药材甲(Stegobium paniceum)、茎干象属(Sternechusspp.)(例如豆茎象(Sternechus paludatus))、宽幅天牛属(Symphyletes spp.)、纤毛象属(Tanymecus spp.)(例如双宽隆突纤毛象(Tanymecus dilaticollis)、印度纤毛象(Tanymecus indicus)、红豆草灰象甲(Tanymecus palliatus))、黄粉虫(Tenebriomolitor)、大谷盗(Tenebrioides mauretanicus)、拟谷盗属(Tribolium spp.)(例如美洲黑拟谷盗(Tribolium audax)、赤拟谷盗(Tribolium castaneum)、杂拟谷盗(Triboliumconfusum))、斑皮蠹属(Trogoderma spp.)、籽象属(Tychius spp.)、脊虎天牛属(Xylotrechus spp.)、距步甲属(Zabrus spp.)(例如玉米距步甲(Zabrustenebrioides));
革翅目(Dermaptera)的害虫,例如,肥螋(Anisolabis maritime)、欧洲球螋(Forficula auricularia)、溪岸蠼螋(Labidura riparia);
双翅目(Diptera)的害虫,例如,伊蚊属(Aedes spp.)(例如埃及伊蚊(Aedesaegypti)、白纹伊蚊(Aedes albopictus)、叮刺伊蚊(Aedes sticticus)、骚扰伊蚊(Aedesvexans))、潜蝇属(Agromyza spp.)(例如苜蓿斑潜蝇(Agromyza frontella)、美洲黍潜蝇(Agromyza parvicornis))、按实蝇属(Anastrepha spp.)、按蚊属(Anopheles spp.)(例如四斑按蚊(Anopheles quadrimaculatus)、冈比亚按蚊(Anopheles gambiae))、瘿蚊属(Asphondylia spp.)、果实蝇属(Bactrocera spp.)(例如瓜实蝇(Bactroceracucurbitae)、东方果实蝇(Bactrocera dorsalis)、油橄榄果实蝇(Bactrocera oleae))、花园毛蚊(Bibio hortulanus)、天青丽蝇(Calliphora erythrocephala)、红头丽蝇(Calliphora vicina)、地中海实蝇(Ceratitis capitata)、摇蚊属(Chironomus spp.)、金蝇属(Chrysomya spp.)、斑虻属(Chrysops spp.)、高额麻虻(Chrysozona pluvialis)、锥蝇属(Cochliomya spp.)、康瘿蚊属(Contarinia spp.)(例如葡萄瘿蚊(Contariniajohnsoni)、甘蓝瘿蚊(Contarinia nasturtii)、梨实康瘿蚊(Contarinia pyrivora)、向日葵瘿蚊(Contarinia schulzi)、高粱康瘿蚊(Contarinia sorghicola)、麦黄康癭蚊(Contarinia tritici))、人皮蝇(Cordylobia anthropophaga)、环足摇蚊(Cricotopussylvestris)、库蚊属(Culex spp.)(例如尖音库蚊(Culex pipiens)、致倦库蚊(Culexquinquefasciatus))、库蠓属(Culicoides spp.)、脉毛蚊属(Culiseta spp.)、黄蝇属(Cuterebra spp.)、橄榄大实蝇(Dacus oleae)、叶瘿蚊属(Dasineura spp.)(例如油菜叶瘿蚊(Dasineura brassicae))、地种蝇属(Delia spp.)(例如葱蝇(Delia antiqua)、麦种蝇(Delia coarctata)、毛跗地种蝇(Delia florilega)、灰地种蝇(Delia platura)、甘蓝地种蝇(Delia radicum))、人肤蝇(Dermatobia hominis)、果蝇属(Drosophila spp.)(例如黑腹果蝇(Drosphila melanogaster)、樱桃果蝇(Drosophila suzukii))、稻象属(Echinocnemus spp.)、Euleia heraclei、厕蝇属(Fannia spp.)、胃蝇属(Gastrophilusspp.)、舌蝇属(Glossina spp.)、麻虻属(Haematopota spp.)、毛眼水蝇属(Hydrelliaspp.)、大麦毛眼水蝇(Hydrellia griseola)、黑蝇属(Hylemya spp.)、虱蝇属(Hippoboscaspp.)、皮蝇属(Hypoderma spp.)、斑潜蝇属(Liriomyza spp.)(例如菜斑潜蝇(Liriomyzabrassicae)、南美斑潜蝇(Liriomyza huidobrensis)、美洲斑潜蝇(Liriomyza sativae))、绿蝇属(Lucilia spp.)(例如铜绿蝇(Lucilia cuprina))、罗蛉属(Lutzomyia spp.)、曼蚊属(Mansonia spp.)、家蝇属(Musca spp.)(例如家蝇(Musca domestica)、舍蝇(Muscadomestica vicina))、狂蝇属(Oestrus spp.)、瑞典麦秆蝇(Oscinella frit)、拟长跑摇蚊属(Paratanytarsus spp.)、Paralauterborniella subcincta、泉蝇属(Pegomya或Pegomyia spp.)(例如甜菜泉蝇(Pegomya betae)、天仙子泉蝇(Pegomya hyoscyami)、悬钩子泉蝇(Pegomya rubivora))、白蛉属(Phlebotomus spp.)、草种蝇属(Phorbia spp.)、伏蝇属(Phormia spp.)、酪蝇(Piophila casei)、Platyparea poeciloptera、Prodiplosis属、胡萝卜茎蝇(Psila rosae)、绕实蝇属(Rhagoletis spp.)(例如东部樱桃实蝇(Rhagoletis cingulata)、核桃绕实蝇(Rhagoletis completa)、黑樱桃实蝇(Rhagoletisfausta)、西部樱桃实蝇(Rhagoletis indifferens)、越桔实蝇(Rhagoletis mendax)、苹果实蝇(Rhagoletis pomonella))、麻蝇属(Sarcophaga spp.)、蚋属(Simulium spp.)(例如南方蚋(Simulium meridionale))、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、根斑蝇属(Tetanops spp.)、大蚊属(Tipula spp.)(例如欧洲大蚊(Tipula paludosa)、牧场大蚊(Tipula simplex))、Toxotrypana curvicauda;
半翅目(Hemiptera)的害虫,例如Acizzia acaciaebaileyanae、Acizziadodonaeae、木虱(Acizzia uncatoides)、长头蝗(Acrida turrita)、无网长管蚜属(Acyrthosipon spp.)(例如豌豆长管蚜(Acyrthosiphon pisum))、Acrogonia属、Aeneolamia属、隆脉木虱属(Agonoscena spp.)、刺粉虱属(Aleurocanthus spp.)、欧洲甘蓝粉虱(Aleyrodes proletella)、蔗粉穴粉虱(Aleurolobus barodensis)、棉粉虱(Aleurothrixus floccosus)、植莲木风(Allocaridara malayensis)、芒果叶蝉属(Amrasca spp.)(例如小绿叶蝉(Amrasca bigutulla)、小叶蝉(Amrasca devastans))、圆尾蚜(Anuraphis cardui)、肾圆盾蚧属(Aonidiella spp.)(例如红肾圆盾蚧(Aonidiellaaurantii)、黄肾圆盾蚧(Aonidiella citrina)、苏铁肾盾蚧(Aonidiella inornata))、梨瘤蚜(Aphanostigma piri)、蚜属(Aphis spp.)(例如绣线菊蚜(Aphis citricola)、黑豆蚜(Aphis craccivora)、甜菜蚜(Aphis fabae)、草莓根蚜(Aphis forbesi)、大豆蚜(Aphisglycines)、棉蚜(Aphis gossypii)、常春藤蚜(Aphis hederae)、葡萄藤蚜(Aphisillinoisensis)、Aphis middletoni、鼠李马铃薯蚜(Aphis nasturtii)、夹竹桃蚜(Aphisnerii)、苹果蚜(Aphis pomi)、卷叶蚜(Aphis spiraecola)、Aphis viburniphila)、葡萄叶蜂(Arboridia apicalis)、Arytainilla属、小圆盾蚧属(Aspidiella spp.)、圆盾蚧属(Aspidiotus spp.)(例如常春藤圆盾蚧(Aspidiotus nerii))、Atanus属、茄沟无网蚜(Aulacorthum solani)、烟粉虱(Bemisia tabaci)、澳大利亚木虱(Blastopsyllaoccidentalis)、Boreioglycaspis melaleucae、李短尾蚜(Brachycaudus helichrysii)、微管姆属(Brachycolus spp.)、甘蓝蚜(Brevicoryne brassicae)、喀木虱属(Cacopsyllaspp.)(例如梨木虱(Cacopsylla pyricola))、小褐稻虱(Calligypona marginata)、Capulinia属、丽黄头大叶蝉(Carneocephala fulgida)、甘蔗绵蚜(Ceratovacunalanigera)、沫蝉科(Cercopidae)、蜡蚧属(Ceroplastes spp.)、草莓钉蚜(Chaetosiphonfragaefolii)、蔗黄雪盾蚧(Chionaspis tegalensis)、茶绿叶蜂(Chlorita onukii)、台湾大蝗(Chondracris rosea)、核桃黑斑蚜(Chromaphis juglandicola)、黑褐圆盾蚧(Chrysomphalus aonidum)、黑褐圆盾蚧(Chrysomphalus ficus)、玉米叶蝉(Cicadulinambila)、Coccomytilus halli、软蚧属(Coccus spp.)(例如褐软蚧(Coccus hesperidum)、长椭圆软蚧(Coccus longulus)、桔软蜡蚧(Coccus pseudomagnoliarum)、咖啡绿蚧(Coccus viridis))、隐瘤蚜(Cryptomyzus ribis)、Cryptoneossa属、梳木风属(Ctenarytaina spp.)、黄翅叶蝶属(Dalbulus spp.)、Dialeurodes chittendeni、柑橘粉虱(Dialeurodes citri)、柑橘木虱(Diaphorina citri)、白背盾蚧属(Diaspis spp.)、Diuraphis属、Doralis属、履绵蚧属(Drosicha spp.)、西圆尾蚜属(Dysaphis spp.)(例如锈条蚜(Dysaphis apiifolia)、车前草蚜(Dysaphis plantaginea)、百合西圆尾蚜(Dysaphis tulipae))、灰粉蚧属(Dysmicoccus spp.)、小绿叶蝉属(Empoasca spp.)(例如西部马铃薯叶蝉(Empoasca abrupta)、蚕豆小叶蝉(Empoasca fabae)、苹果小绿叶蝉(Empoasca maligna)、茄微叶蝉(Empoasca solana)、Empoasca stevensi、绵蚜属(Eriosoma spp.)(例如美洲绵蚜(Eriosoma americanum)、苹果绵蚜(Eriosomalanigerum)、梨根绵蚜(Eriosoma pyricola))、斑叶蝉属(Erythroneura spp.)、Eucalyptolyma属、褐木虱属(Euphyllura spp.)、殃叶蝉(Euscelis bilobatus)、拂粉阶属(Ferrisia spp.)、Fiorinia属、Furcaspis oceanica、咖啡地粉蚧(Geococcus coffeae)、Glycaspis属、银合欢木虱(Heteropsylla cubana)、颊木虱(Heteropsylla spinulosa)、假桃病毒叶蝉(Homalodisca coagulata)、梅大尾蚜(Hyalopterus arundinis)、桃大尾蚜(Hyalopterus pruni)、吹绵蚧属(Icerya spp.)(例如吹绵蚧壳虫(Icerya purchasi))、Idiocerus属、扁喙叶蝉属(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、蜡蚧属(Lecanium spp.)(例如水土坚蚧(Lecanium corni)(=Parthenolecanium corni))、盾蚧属(Lepidosaphes spp.)(例如榆蛎盾蚧(Lepidosaphes ulmi))、萝卜蚜(Lipaphiserysimi)、日本长白蚧(Lopholeucaspis japonica)、斑衣蜡蝉(Lycorma delicatula)、长管蚜属(Macrosiphum spp.)(例如马铃薯长管蚜(Macrosiphum euphorbiae)、百合长管蚜(Macrosiphum lilii)、蔷薇长管蚜(Macrosiphum rosae))、二点叶蜂(Macrostelesfacifrons)、沫蝶属(Mahanarva spp.)、高粱蚜(Melanaphis sacchari)、Metcalfiella属、Metcalfa pruinosa、麦无网蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monelliacostalis)、Monelliopsis pecanis、瘤蚜属(Myzus spp.)(例如冬葱瘤蚜(Myzusascalonicus)、梅瘤蚜(Myzus cerasi)、女贞瘤蚜(Myzus ligustri)、堇菜瘤蚜(Myzusornatus)、桃蚜(Myzus persicae)、烟蚜(Myzus nicotianae))、莴苣衲长管蚜(Nasonoviaribisnigri)、Neomaskellia属、黑尾叶蝉属(Nephotettix spp.)(例如黑尾叶蝉(Nephotettix cincticeps)、二条黑尾叶蝉(Nephotettix nigropictus))、Nettigonicllaspectra、褐飞虱(Nilaparvata lugens)、Oncometopia属、Orthezia praelonga、中华稻蝗(Oxya chinensis)、Pachypsylla属、杨梅粉虱(Parabemisia myricae)、虱啮属(Paratrioza spp.)(例如马铃薯木虱(Paratrioza cockerelli))、片盾蚧属(Parlatoriaspp.)、瘿绵蚜属(Pemphigus spp.)(例如囊柄瘿绵蚜(Pemphigus bursarius)、Pemphiguspopulivenae)、玉米蜡蝉(Peregrinus maidis)、Perkinsiella属、绵粉蚧属(Phenacoccusspp.)(例如美地绵粉蚧(Phenacoccus madeirensis))、杨平翅绵蚜(Phloeomyzuspasserinii)、忽布疣蚜(Phorodon humuli)、葡萄根瘤蚜属(Phylloxera spp.)(例如Phylloxera devastatrix、警根瘤蚜(Phylloxera notabilis))、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、臀纹粉蚧属(Planococcus spp.)(例如橘臀纹粉蚧(Planococcus citri))、Prosopidopsylla flava、梨形原绵腊蚧(Protopulvinariapyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属(Pseudococcus spp.)(例如柑栖粉蚧(Pseudococcus calceolariae)、康氏粉蚧(Pseudococcus comstocki)、拟长尾粉蚧(Pseudococcus longispinus)、葡萄粉蚧(Pseudococcus maritimus)、暗色粉蚧(Pseudococcus viburni))、Psyllopsis属、木虱属(Psylla spp.)(例如黄杨木虱(Psyllabuxi)、苹木虱(Psylla mali)、梨木虱(Psylla pyri))、金小蜂属(Pteromalus spp.)、桃绵蜡蚧(Pulvinaria spp.)、Pyrilla属、笠圆盾蚧属(Quadraspidiotus spp.)(例如胡桃园盾蚧(Quadraspidiotus juglansregiae)、杨笠圆盾蚧(Quadraspidiotus ostreaeformis)、梨笠盾蚧(Quadraspidiotus perniciosus))、Quesada gigas、平刺粉蚧属(Rastrococcusspp.)、缢管蚜属(Rhopalosiphum spp.)(例如玉米蚜(Rhopalosiphum maidis)、苹草缢管蚜(Rhopalosiphum oxyacanthae)、稻麦蚜(Rhopalosiphum padi)、红腹缢管蚜(Rhopalosiphum rufiabdominale))、黑盔蚧属(Saissetia spp.)(例如咖啡黑盔蚧(Saissetia coffeae)、Saissetia miranda、Saissetia neglecta、黑蜡蚧(Saissetiaoleae))、葡萄带叶蝉(Scaphoideus titanus)、麦二叉蚜(Schizaphis graminum)、苏铁刺圆盾蚧(Selenaspidus articulatus)、Sipha flava、麦长管蚜(Sitobion avenae)、长唇基飞虱属(Sogata spp.)、白背飞虱(Sogatella furcifera)、稻飞风属(Sogatodes spp.)、Stictocephala festina、树粉虱(Siphoninus phillyreae)、Tenalaphara malayensis、Tetragonocephela属、长斑蚜属(Tinocallis caryaefoliae)、广胸沫蝉属(Tomaspisspp.)、声蚜属(Toxoptera spp.)(例如小桔蚜(Toxoptera aurantii)、大桔蚜(Toxopteracitricidus))、温室粉虱(Trialeurodes vaporariorum)、尖翅木虱属(Trioza spp.)(例如柿木虱(Trioza diospyri))、小叶蝉属(Typhlocyba spp.)、尖盾蚧属(Unaspis spp.)、葡萄根瘤蚜(Viteus vitifolii)、么叶蝉属(Zygina spp.);
异翅亚目(Heteroptera)的害虫,例如,Aelia属、南瓜缘蝽(Anasa tristis)、拟丽蝽属(Antestiopsis spp.)、Boisea属、土长蝽属(Blissus spp.)、俊盲蝽属(Calocorisspp.)、斑腿微剌盲蝽(Campylomma livida)、异背长蝽属(Cavelerius spp.)、臭虫属(Cimex spp.)(例如Cimex adjunctus、热带臭虫(Cimex hemipterus)、温带臭虫(Cimexlectularius)、蝠臭虫(Cimex pilosellus))、白瓣麦寄蝇属(Collaria spp.)、绿盲蝽(Creontiades dilutus)、胡椒缘蝽(Dasynus piperis)、Dichelops furcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属(Dysdercus spp.)、美洲蝽属(Euschistus spp.)(例如英雄美洲蝽(Euschistus heros)、褐美洲蝽(Euschistus servus)、三色美洲蝽(Euschistus tristigmus)、三点美洲蝽(Euschistus variolarius))、菜蝽属(Eurydemaspp.)、扁盾蝽属(Eurygaster spp.)、茶翅蝽(Halyomorpha halys)、盲蝽属(Heliopeltisspp.)、Horcias nobilellus、稻缘蝽属(Leptocorisa spp.)、异稻缘蝽(Leptocorisavaricornis)、西部喙缘蝽(Leptoglossus occidentalis)、叶缘缘蝽(Leptoglossusphyllopus)、丽盲蝽属(Lygocoris spp.)(例如原丽盲蝽(Lygocoris pabulinus))、草盲蝽属(Lygus spp.)(例如灰豆草盲蝽(Lygus elisus)、豆荚草盲蝽(Lygus hesperus)、美国牧草盲蝽(Lygus lineolaris))、蔗黑长蝽(Macropes excavatus)、Megacopta cribraria、Miridae、金光绿盲蝽(Monalonion atratum)、绿蝽属(Nezara spp.)(例如稻绿蝽(Nezaraviridula))、Nysius属、稻蝽属(Oebalus spp.)、Pentomidae、方背皮蝽(Piesmaquadrata)、璧蝽属(Piezodorus spp.)(例如盖德拟壁蝽(Piezodorus guildinii))、盲蝽属(Psallus spp.)、Pseudacysta persea、红猎蝽属(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、Scaptocoris castanea、黑蝽属(Scotinophora spp.)、梨冠网蝽(Stephanitis nashi)、Tibraca属、锥猎蝽属(Triatoma spp.);
膜翅目(Hymenoptera)的害虫,例如,顶切叶蚁属(Acromyrmex spp.)、菜叶蜂属(Athalia spp.)(例如黄翅菜叶蜂(Athalia rosae))、美切叶蚁属(Atta spp.)、弓背蚁属(Camponotus spp.)、Dolichovespula属、松叶蜂属(Diprion spp.)(例如类欧松叶蜂(Diprion similis))、实叶蜂属(Hoplocampa spp.)(例如樱实叶蜂(Hoplocampa cookei)、苹叶蜂(Hoplocampa testudinea))、毛蚁属(Lasius spp.)、阿根廷蚁(Linepithema(Iridiomyrmex)humile)、小家蚁(Monomorium pharaonis)、立毛蚁属(Paratrechinaspp.)、Paravespula属、Plagiolepis属、树蜂属(Sirex spp.)(例如云杉蓝树蜂(Sirexnoctilio))、红火蚁(Solenopsis invicta)、臭蚁属(Tapinoma spp.)、白足狡臭蚁(Technomyrmex albipes)、大树蜂属(Urocerus spp.)、胡蜂属(Vespa spp.)(例如黄边胡蜂(Vespa crabro))、小火蚁(Wasmannia auropunctata)、黑树蜂属(Xeris spp.);
等足目(Isopoda)的害虫,例如,鼠妇(Armadillidium vulgare)、栉水虱(Oniscusasellus)、球鼠妇(Porcellio scaber);
等翅目(Isoptera)的害虫,例如,家白蚁属(Coptotermes spp.)(例如台湾乳白蚁(Coptotermes formosanus))、堆角白蚁(Cornitermes cumulans)、堆砂白蚁属(Cryptotermes spp.)、楹白蚁属(Incisitermes spp.)、木白蚁属(Kalotermes spp.)、稻麦小白蚁(Microtermes obesi)、鼻白蚁属(Nasutitermes spp.)、土白蚁属(Odontotermesspp.)、Porotermes属、散白蚁属(Reticulitermes spp.)(例如黄肢散白蚁(Reticulitermes flavipes)、美国散白蚁(Reticulitermes hesperus));
鳞翅目(Lepidoptera)的害虫,例如,小蜡螟(Achroia grisella)、桑剑纹夜蛾(Acronicta major)、褐带卷蛾属(Adoxophyes spp.)(例如棉褐带卷蛾(Adoxophyesorana))、烦夜蛾(Aedia leucomelas)、地老虎属(Agrotis spp.)(例如黄地老虎(Agrotissegetum)、小地老虎(Agrotis ipsilon))、波纹夜蛾属(Alabama spp.)(例如棉叶波纹夜蛾(Alabama argillacea))、脐橙螟(Amyelois transitella)、条麦蛾属(Anarsia spp.)、干煞夜蛾属(Anticarsia spp.)(例如大豆夜蛾(Anticarsia gemmatalis))、条小卷蛾属(Argyroploce spp.)、苜蓿银纹夜蛾属(Autographa spp.)、甘蓝夜蛾(Barathrabrassicae)、苹髓尖蛾(Blastodacna atra)、籼弄蝶(Borbo cinnara)、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、蛀褐夜蛾属(Busseolaspp.)、卷叶蛾属(Cacoecia spp.)、茶细蛾(Caloptilia theivora)、烟卷蛾(Capuareticulana)、苹果小卷蛾(Carpocapsa pomonella)、桃蛀果蛾(Carposina niponensis)、冬尺蛾(Cheimatobia brumata)、禾草螟属(Chilo spp.)(例如Chilo plejadellus、二化螟(Chilo suppressalis))、Choreutis pariana、色卷蛾属(Choristoneura spp.)、Chrysodeixis chalcites、葡萄果蠹蛾(Clysia ambiguella)、纵卷叶野螟属(Cnaphalocerus spp.)、稻纵卷叶野螟(Cnaphalocrocis medinalis)、云卷蛾属(Cnephasia spp.)、茶枝尖细蛾属(Conopomorpha spp.)、球颈象属(Conotrachelusspp.)、Copitarsia属、小卷蛾属(Cydia spp.)(例如豆荚小卷蛾(Cydia nigricana)、苹果蠹蛾(Cydia pomonella))、Dalaca noctuides、绢野螟属(Diaphania spp.)、Diparopsis属、小蔗杆草螟(Diatraea saccharalis)、梢斑螟属(Dioryctria spp.)(例如Dioryctriazimmermani)、钻夜蛾属(Earias spp.)、Ecdytolopha aurantium、南美玉米苗斑螟(Elasmopalpus lignosellus)、甘薯杆螟(Eldana saccharina)、粉斑螟属(Ephestiaspp.)(例如烟草粉斑螟(Ephestia elutella)、地中海斑螟(Ephestia kuehniella))、叶小卷蛾属(Epinotia spp.)、苹淡褐卷蛾(Epiphyas postvittana)、Erannis属、亚洲胡桃蛾(Erschoviella musculana)、荚斑螟属(Etiella spp.)、Eudocima属、棕卷蛾属(Euliaspp.)、女贞细卷蛾(Eupoecilia ambiguella)、毒蛾属(Euproctis spp.)(例如黄毒蛾(Euproctis chrysorrhoea))、切夜蛾属(Euxoa spp.)、脏切夜蛾属(Feltia spp.)、大蜡螟(Galleria mellonella)、细蛾属(Gracillaria spp.)、小食心虫属(Grapholitha spp.)(例如梨小食心虫(Grapholita molesta)、杏小食心虫(Grapholita prunivora))、甘蔗螟属(Hedylepta spp.)、铃夜蛾属(Helicoverpa spp.)(例如棉铃虫(Helicoverpaarmigera)、玉米夜蛾(Helicoverpa zea))、实夜蛾属(Heliothis spp.)(例如烟芽夜蛾(Heliothis virescens))、Hepialus spp.(例如Hepialus humuli)、褐织蛾(Hofmannophila pseudospretella)、同斑螟属(Homoeosoma spp.)、长卷蛾属(Homonaspp.)、苹果巢蛾(Hyponomeuta padella)、柿举枝蛾(Kakivoria flavofasciata)、亮灰蝶属(Lampides spp.)、贪夜蛾属(Laphygma spp.)、蠹食心虫(Laspeyresia molesta)、茄白翅野螟(Leucinodes orbonalis)、纹潜蛾属(Leucoptera spp.)(例如咖啡潜叶蛾(Leucoptera coffeella))、潜叶细蛾属(Lithocolletis spp.)(例如苹果斑幕潜叶蛾(Lithocolletis blancardella))、绿果冬夜蛾(Lithophane antennata)、花翅小蛾属(Lobesia spp.)(例如葡萄花翅小卷蛾(Lobesia botrana))、豆白隆切根虫(Loxagrotisalbicosta)、毒蛾属(Lymantria spp.)(例如舞毒蛾(Lymantria dispar))、潜蛾属(Lyonetia spp.)(例如桃潜叶蛾(Lyonetia clerkella))、黄褐天幕毛虫(Malacosomaneustria)、豆荚野螟(Maruca testulalis)、甘蓝夜蛾(Mamstra brassicae)、稻暮眼蝶(Melanitis leda)、毛胫夜蛾属(Mocis spp.)、Monopis obviella、粘虫(Mythimnaseparata)、橡长角蛾(Nemapogon cloacellus)、水螟属(Nymphula spp.)、Oiketicus属、楸属(Omphisa spp.)、Operophtera属、麦秆夜蛾属(Oria spp.)、瘤丛螟属(Orthaga spp.)、秆野螟属(Ostrinia spp.)(例如欧洲玉米螟(Ostrinia nubilalis))、小眼夜蛾(Panolisflammea)、稻弄蝶属(Parnara spp.)、红铃虫属(Pectinophora spp.)(例如棉红铃虫(Pectinophora gossypiella))、潜跳甲属(Perileucoptera spp.)、茄麦蛾属(Phthorimaea spp.)(例如马铃薯麦蛾(Phthorimaea operculella))、桔潜蛾(Phyllocnistis citrella)、小潜细蛾属(Phyllonorycter spp.)(例如金纹小潜细蛾(Phyllonorycter blancardella)、山楂潜叶蛾(Phyllonorycter crataegella))、粉蝶属(Pieris spp.)(例如菜粉蝶(Pieris rapae))、荷兰石竹小卷蛾(Platynota stultana)、印度谷斑螟(Plodia interpunctella)、金翅夜蛾属(Plusia spp.)、菜蛾(Plutellaxylostella)(=钻石背蛾(Plutella maculipennis))、Podesia属(例如Podesiasyringae)、小白巢蛾属(Prays spp.)、斜纹夜蛾属(Prodenia spp.)、烟草天蛾属(Protoparce spp.)、粘虫属(Pseudaletia spp.)(例如一星粘虫(Pseudaletiaunipuncta))、大豆尺夜蛾(Pseudoplusia includens)、玉米螟(Pyrausta nubilalis)、薄荷灰夜蛾(Rachiplusia nu)、禾螟属(Schoenobius spp.)(例如三化螟(Schoenobiusbipunctifer))、白禾螟属(Scirpophaga spp.)(例如稻白螟(Scirpophaga innotata))、黄地老虎(Scotia segetum)、茎夜蛾属(Sesamia spp.)(例如大螟(Sesamia inferens))、长须卷蛾属(Sparganothis spp.)、灰翅夜蛾属(Spodoptera spp.)(例如Spodopteraeradiana、甜菜夜蛾(Spodoptera exigua)、草地贪夜蛾(Spodoptera frugiperda)、Spodoptera praefica、展足蛾属(Stathmopoda spp.)、Stenoma属、花生麦蛾(Stomopteryxsubsecivella)、透翅蛾属(Synanthedon spp.)、安第斯马铃薯块茎蛾(Teciasolanivora)、异舟蛾属(Thaumetopoea spp.)、大豆夜蛾(Thermesia gemmatalis)、木塞谷蛾(Tinea cloacella)、袋谷蛾(Tinea pellionella)、幕谷蛾(Tineola bisselliella)、卷蛾属(Tortrix spp.)、毛毡衣蛾(Trichophaga tapetzella)、粉夜蛾属(Trichoplusiaspp.)(例如粉纹夜蛾(Trichoplusia ni))、三化螟(Tryporyza incertulas)、番茄斑潜蝇(Tuta absoluta)、灰蝶属(Virachola spp.);
直翅目(Orthoptera)或跳跃目(Saltatoria)的害虫,例如,家蟋蟀(Achetadomesticus)、Dichroplus属、蝼蛄属(Gryllotalpa spp.)(例如欧洲蝼蛄(Gryllotalpagryllotalpa))、蔗蝗属(Hieroglyphus spp.)、飞蝗属(Locusta spp.)(例如飞蝗(Locustamigratoria))、黑蝗属(Melanoplus spp.)(例如迁飞黑蝗(Melanoplus devastator)、Paratlanticus ussuriensis)、沙漠蝗(Schistocerca gregaria);
虱目(Phthiraptera)的害虫,例如,例如畜虱属(Damalinia spp.)、血虱属(Haematopinus spp.)、毛虱属(Linognathus spp.)、虱属(Pediculus spp.)、根瘤蚜(Phylloxera vastatrix)、阴虱(Ptirus pubis)、啮毛虱属(Trichodectes spp.);
啮虫目(Psocoptera)的害虫,例如,粉啮虫属(Lepinatus spp.)、书虱属(Liposcelis spp.);
蚤目(Siphonaptera)的害虫,例如,角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)(例如犬栉头蚤(Ctenocephalides canis),猫栉头蚤(Ctenocephalides felis))、跳蚤(Pulex irritans)、穿皮潜蚤(Tunga penetrans)、印鼠客蚤(Xenopsylla cheopis);
缨翅目(Thysanoptera)的害虫,例如,玉米黄呆蓟马(Anaphothrips obscurus)、稻蓟马(Baliothrips biformis)、Chaetanaphothrips leeuweni、葡萄镰蓟马(Drepanothris reuteri)、Enneothrips flavens、花蓟马属(Frankliniella spp.)(例如烟褐蓟马(Frankliniella fusca)、西花蓟马(Frankliniella occidentalis)、苏花蓟马(Frankliniella schultzei)、麦花蓟马(Frankliniella tritici)、越桔花蓟马(Frankliniella vaccinii)、威廉期花蓟马(Frankliniella williamsi))、蓟马属(Haplothrips spp.)、阳蓟马属(Heliothrips spp.)、温室条篱蓟马(Hercinothripsfemoralis)、卡蓟马属(Kakothrips spp.)、葡萄蓟马(Rhipiphorothrips cruentatus)、硬蓟马属(Scirtothrips spp.)、小豆蘧带蓟马(Taeniothrips cardamomi)、蓟马属(Thripsspp.)(例如棕榈蓟马(Thrips palmi)、烟蓟马(Thrips tabaci));
衣鱼目(Zygentoma)(=缨尾亚目(Thysanura))的害虫,例如,栉衣鱼属(Ctenolepisma spp.)、衣鱼(Lepisma saccharina)、盗火虫(Lepismodes inquilinus)、家衣鱼(Thermobia domestica);
综合纲(Symphyla)的害虫,例如,幺蚰属(Scutigerella spp.)(例如无斑点幺蚰(Scutigerella immaculata));
软体动物门(Mollusca)的害虫,例如双壳纲(Bivalvia)的害虫,如饰贝属(Dreissena spp.),
以及腹足纲(Gastropoda)的害虫,如阿勇蛞蝓属(Arion spp.)(例如黑红阿勇蛞蝓(Arion ater rufus))、双脐螺属(Biomphalaria spp.)、小泡螺属(Bulinus spp.)、野蛞蝓属(Deroceras spp.)(例如田灰蛞蝓(Deroceras laeve))、土蜗属(Galba spp.)、椎实螺属(Lymnaea spp.)、钉螺属(Oncomelania spp.)、福寿螺属(Pomacea spp.)、琥珀螺属(Succinea spp.);
线虫纲(Nematoda)的植物害虫,即植物寄生性线虫,尤其是野外垫刃线虫属(Aglenchus spp.)(例如居农野外垫刃线虫(Aglenchus agricola))、粒线虫属(Anguinaspp.)(例如小麦粒线虫(Anguina tritici))、滑刃线虫属(Aphelenchoides spp.)(例如花生滑刃线虫(Aphelenchoides arachidis)、草莓滑刃线虫(Aphelenchoides fragariae))、刺线虫属(Belonolaimus spp.)(例如细小刺线虫(Belonolaimus gracilis)、长尾刺线虫(Belonolaimus longicaudatus)、诺顿刺线虫(Belonolaimus nortoni))、伞滑刃线虫属(Bursaphelenchus spp.)(例如椰子红环腐线虫(Bursaphelenchus cocophilus)、荒漠伞滑刃线虫(Bursaphelenchus eremus)、松材线虫(Bursaphelenchus xylophilus))、坏死线虫属(Cacopaurus spp.)(例如瘟疫坏死线虫(Cacopaurus pestis))、小环线虫属(Criconemella spp.)(例如弯曲小环线虫(Criconemella curvata)、刻线小环线虫(Criconemella onoensis)、装饰小环线虫(Criconemella ornata)、畸形小环线虫(Criconemella rusium)、薄叶小环线虫(Criconemella xenoplax(=环腐线虫(Mesocriconema xenoplax))))、轮线虫属(Criconemoides spp.)(例如Criconemoidesferniae、Criconemoides onoense、Criconemoides ornatum)、双垫刃属(Ditylenchusapp.)(例如续断双垫刃线虫(Ditylenchus dipsaci))、锥线虫属(Dolichodorus spp.)、球异皮线虫属(Globodera spp.)(例如马铃薯白线虫(Globodera pallida)、马铃薯金线虫(Globodera rostochiensis))、螺旋线虫属(Helicotylenchus spp.)(例如双宫螺旋线虫(Helicotylenchus dihystera))、半轮线虫属(Hemicriconemoides spp.)、鞘线虫属(Hemicycliophora spp.)、异皮线虫属(Heterodera spp.)(例如燕麦胞囊线虫(Heterodera avenae)、大豆胞囊线虫(Heterodera glycines)、甜菜胞囊线虫(Heteroderaschachtii))、Hirschmaniella属、纽带线虫属(Hoplolaimus spp.)、长针线虫属(Longidorus spp.)(例如非洲长针线虫(Longidorus africanus))、根结线虫属(Meloidogyne spp.)(例如哥伦比亚根结线虫(Meloidogyne chitwoodi)、伪根结线虫(Meloidogyne fallax)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyneincognita))、瓢线虫属(Meloinema spp.)、珍珠线虫属(Nacobbus spp.)、拟茎线虫属(Neotylenchus spp.)、拟长针线虫属(Paralongidorus spp.)、拟滑刃线虫属(Paraphelenchus spp.)、拟毛刺线虫属(Paratrichodorus spp.)(例如次拟毛刺线虫(Paratrichodorus minor))、针线虫属(Paratylenchus spp.)、短体线虫属(Pratylenchusspp.)(例如穿刺短体线虫(Pratylenchus penetrans))、Pseudohalenchus属、平滑垫刃属(Psilenchus spp.)、斑皮胞囊线虫属(Punctodera spp.)、五沟线虫属(Quinisulciusspp.)、穿孔线虫属(Radopholus spp.)(例如柑桔穿孔线虫(Radopholus citrophilus)、香蕉穿孔线虫(Radopholus similis))、肾状线虫属(Rotylenchulus spp.)、盘旋线虫属(Rotylenchus spp.)、盾线虫属(Scutellonema spp.)、亚蛇形线虫属(Subanguina spp.)、毛刺线虫属(Trichodorus spp.)(例如短粗根毛刺线虫(Trichodorus obtusus)、原始毛刺线虫(Trichodorus primitivus))、矮化线虫属(Tylenchorhynchus spp.)(例如饰环矮化线虫(Tylenchorhynchus annulatus))、麦线虫属(Tylenchulus spp.)(例如柑桔根线虫(Tylenchulus semipenetrans))、剑线虫属(Xiphinema spp.)(例如标准剑线虫(Xiphinema index))。
在一定的浓度或施用率下,还可将式(I)的化合物任选地用作除草剂、安全剂、生长调节剂或改善植物特性的试剂,用作杀微生物剂或杀配子剂,例如用作杀真菌剂、抗霉菌剂、杀细菌剂、杀病毒剂(包括对抗类病毒的试剂)或用作对抗MLO(类支原体生物)和RLO(类立克次氏体生物)的试剂。如果合适的话,它们还可用作用于合成其他活性化合物的中间体或前体。
制剂/使用形式
本发明还涉及制剂,特别是用于防治有害动物害虫的制剂。所述制剂可以应用于动物害虫和/或它们的生境。
本发明的制剂可以作为“即用型”使用形式提供给最终用户,即可以通过合适的装置如喷雾器或喷粉器将制剂直接施用于植物或种子。或者,制剂可以以在使用前必须被稀释、优选用水稀释的浓缩物的形式提供给最终用户。除非另有说明,术语“制剂”因此是指这样的浓缩物,而术语“使用形式”是指一种对最终用户为“即用型”的溶液,即通常为这样的稀释制剂。
本发明的制剂可以以常规方法制备,例如通过使本发明的化合物与一种或多种合适的助剂(例如本文所公开的)混合。
所述制剂包含至少一种本发明的化合物和至少一种农业上合适的助剂,例如载体和/或表面活性剂。
载体通常为惰性的固体或液体、天然的或合成的、有机或无机物质。载体通常改进化合物的应用,例如对植物、植物部分或种子的应用。合适的固体载体的实例包括但不限于铵盐,特别是硫酸铵、磷酸铵和硝酸铵;天然岩石粉,例如高岭土、粘土、滑石、白垩、石英、绿坡缕石(attapulgite)、蒙脱石和硅藻土、硅胶和合成岩石粉,例如精细研磨的二氧化硅、氧化铝和硅酸盐。通常有用的用于制备颗粒的固体载体的实例包括但不限于压碎并分级的天然岩石,例如方解石、大理石、浮石、海泡石和白云石,以及无机粉末和有机粉末的合成颗粒以及有机材料的颗粒例如纸、锯屑、椰壳、玉米穗轴和烟草茎。合适的液体载体的实例包括但不限于水、有机溶剂及其组合。合适溶剂的实例包括极性和非极性有机化学液体,例如芳族和非芳族烃类(例如环己烷、链烷烃、烷基苯、二甲苯、甲苯、四氢萘、烷基萘、氯化芳烃或氯化脂族烃如氯苯、氯乙烯或二氯甲烷),醇和多元醇(也可以任选地被取代、醚化和/或酯化,例如乙醇、丙醇、丁醇、苯甲醇、环己醇或乙二醇),酮(例如丙酮、甲基乙基酮、甲基异丁基酮、苯乙酮或环己酮),酯(包括脂肪和油)和(聚)醚,未被取代和取代的胺,酰胺(例如二甲基甲酰胺或脂肪酸酰胺)及其酯、内酰胺(例如N-烷基吡咯烷酮,特别是N-甲基吡咯烷酮)和内酯,砜和亚砜(如二甲基亚砜),植物油或动物油,腈(烷基腈如乙腈、丙腈、丁腈或芳族腈如苯甲腈),碳酸酯(环状碳酸酯如碳酸亚乙酯、碳酸亚丙酯、碳酸亚丁酯,或碳酸二烷基酯如碳酸二甲酯、碳酸二乙酯、碳酸二丙酯、碳酸二丁酯、碳酸二辛酯)。载体也可以是液化的气体增量剂,即在标准温度和标准压力下呈气态的液体,例如气溶胶推进剂,例如卤代烃、丁烷、丙烷、氮气和二氧化碳。
优选的固体载体选自粘土、滑石和二氧化硅。
优选的液体载体选自水、脂肪酸酰胺及其酯、芳族烃和非芳族烃、内酰胺、内酯、碳酸酯、酮和(聚)醚。
载体的量通常为制剂的1至99.99重量%、优选5至99.9重量%、特别优选10至99.5重量%、且最优选20至99重量%。
液体载体通常以制剂的20至90重量%,例如30至80重量%存在。
固体载体通常以制剂的0至50重量%,优选5至45重量%,例如10至30重量%存在。
如果制剂包含两种或更多种载体,则定义的范围是指载体的总量。
表面活性剂可以是离子(阳离子或阴离子)、两性或非离子表面活性剂,例如离子或非离子乳化剂、发泡剂、分散剂、润湿剂、渗透促进剂及其任意混合物。合适的表面活性剂的实例包括但不限于聚丙烯酸盐;乙氧基化聚(α-取代的)丙烯酸酯衍生物;木质素磺酸盐(例如木质素磺酸钠);苯酚磺酸或萘磺酸的盐;环氧乙烷和/或环氧丙烷与或不与醇的缩聚物;脂肪酸或脂肪胺(例如聚氧乙烯脂肪酸酯例如蓖麻油乙氧基化物、聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚);取代的酚(优选烷基酚或芳基酚);磺基琥珀酸酯的盐;牛磺酸衍生物(优选牛磺酸烷基酯);聚乙氧基化醇或酚的磷酸酯;多元醇的脂肪酸酯(例如甘油、山梨糖醇或蔗糖的脂肪酸酯);硫酸盐(例如烷基硫酸盐和烷基醚硫酸盐);磺酸盐(例如烷基磺酸盐、芳基磺酸盐和烷基苯磺酸盐);萘/甲醛的磺化聚合物;磷酸酯;蛋白质水解产物;木质素亚硫酸盐废液和甲基纤维素。在本段中提及的任何盐优选是指相应的碱金属盐、碱土金属盐和铵盐。
优选的表面活性剂选自乙氧基化聚(α-取代的)丙烯酸酯衍生物、环氧乙烷和/或环氧丙烷与醇的缩聚物、聚氧乙烯脂肪酸酯、烷基苯磺酸盐、萘/甲醛的磺化聚合物;聚氧乙烯脂肪酸酯如蓖麻油乙氧基化物、木质素磺酸钠和芳基苯酚乙氧基化物。
表面活性剂的量通常为制剂的5至40重量%,例如10至20重量%。
合适的助剂的其他实例包括防水剂、干燥剂、粘合剂(胶粘剂;增粘剂;固定剂例如羧甲基纤维素;粉末、颗粒或胶乳形式的天然和合成聚合物,例如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯、天然磷脂如脑磷脂和卵磷脂和合成磷脂、聚乙烯吡咯烷酮和甲基纤维素)、增稠剂和二级增稠剂(如纤维素醚、丙烯酸衍生物、黄原胶、改性粘土,例如以膨润土为名的产品和精细研磨的二氧化硅)、稳定剂(例如冷稳定剂、防腐剂(例如二氯酚、苯甲醇半缩甲醛、1,2-苯并异噻唑啉-3-酮、2-甲基-4-异噻唑啉-3-酮)、抗氧化剂、光稳定剂、特别是UV稳定剂和其他改善化学和/或物理稳定性的试剂)、染料或颜料(例如无机颜料,例如氧化铁、氧化钛和普鲁士蓝;有机颜料例如茜素、偶氮和金属酞菁染料)、消泡剂(例如有机硅消泡剂和硬脂酸镁)、防冻剂、黏着剂、赤霉素和加工助剂、矿物油和植物油、香料、蜡、营养素(包括微量营养素,如铁、锰、硼、铜、钴、钼和锌的盐)、保护胶体、触变物质、渗透剂、螯合剂和络合物形成剂。
助剂的选择取决于本发明的化合物的预期应用形式和/或化合物的物理特性。此外,可以选择能够赋予制剂或由其制备的使用形式某些特性(技术、物理和/或生物学特性)的助剂。助剂的选择可以使制剂满足特定需求。
该制剂包含杀昆虫/杀螨/杀线虫有效量的本发明的化合物。术语“有效量”是指足以防治栽培植物上或材料保护中的有害昆虫/螨/线虫并且对所处理的植物不会导致实质损害的量。这样的量可以在宽范围内变化并且取决于各种因素,例如要防治的昆虫/螨/线虫的种属、所处理的栽培植物或材料、气候条件以及所用的本发明的化合物。通常,本发明的制剂包含0.01至99重量%、优选0.05至98重量%、更优选0.1至95重量%、甚至更优选0.5至90重量%、最优选1至80重量%的本发明的化合物。制剂可以包含两种或更多种本发明的化合物。在这类情况下,所定义的范围是指本发明的化合物的总量。
本发明的制剂可以任何常规制剂类型存在,例如溶液(例如水溶液)、乳液、水基和油基悬浮液、粉剂(powder)(例如可湿性粉剂、可溶性粉剂)、粉末剂(dust)、糊剂、粒剂(例如可溶性粒剂、播撒粒剂)、悬乳浓缩剂、用本发明化合物浸渍的天然或合成产品、肥料以及聚合物质中的微胶囊。本发明的化合物可以以悬浮、乳化或溶解的形式存在。特别合适的制剂类型的实例为溶液剂、水溶性浓缩剂(例如SL、LS)、可分散浓缩剂(DC)、悬浮剂和悬浮浓缩剂(例如SC、OD、OF、FS)、乳液浓缩剂(例如EC)、乳剂(例如EW、EO、ES、ME、SE)、胶囊(例如CS、ZC)、糊剂、锭剂、可湿性粉剂或粉末剂(例如WP、SP、WS、DP、DS)、压制剂(例如BR、TB、DT)、颗粒剂(例如WG、SG、GR、FG、GG、MG)、杀虫制品(例如LN)和用于处理植物繁殖材料例如种子的凝胶制剂(例如GW、GF)。这些和其他制剂类型由联合国粮农组织(FAO)定义。综述见“Catalogue of pesticide formulation types and international coding system”,Technical Monograph第2期,第6版,2008年5月,Croplife International。
优选地,本发明的制剂为下列类型之一的形式:EC、SC、FS、SE、OD、WG、WP、CS,更优选EC、SC、OD、WG、CS。
下文给出关于制剂类型及其制备的实例的进一步细节。如果存在两种或更多种本发明的化合物,则本发明化合物的所述量是指本发明化合物的总量。如果存在两种或更多种此类组分(例如润湿剂或粘合剂)的代表,加以适当修改,则这也适用于制剂的所有其他组分。
i)水溶性浓缩剂(SL、LS)
将10至60重量%的至少一种本发明的化合物与5至15重量%的表面活性剂(例如环氧乙烷和/或环氧丙烷与醇的缩聚物)溶于一定量的水和/或水溶性溶剂(例如醇类如丙二醇等或碳酸酯如碳酸亚丙酯)中,使得总量为100重量%。使用前,将浓缩物用水稀释。
ii)可分散浓缩剂(DC)
将5至25重量%的至少一种本发明的化合物与1至10重量%的表面活性剂和/或粘合剂(例如聚乙烯吡咯烷酮)溶于一定量的有机溶剂(例如环己酮)中,使得总量为100重量%。用水稀释得到分散体。
iii)乳液浓缩剂(EC)
将15至70重量%的至少一种本发明的化合物与5至10重量%的表面活性剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物的混合物)溶于一定量的水不溶性有机溶剂(例如芳烃或脂肪酸酰胺)和其他水溶性溶剂(如果需要),使得总量为100重量%。用水稀释得到乳剂。
iv)乳剂(EW、EO、ES)
将5至40重量%的至少一种本发明的化合物与1至10重量%的表面活性剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物的混合物,或环氧乙烷和/或环氧丙烷与或不与醇的缩聚物)溶于20至40重量%的水不溶性有机溶剂(例如芳烃)中。使用乳化机,将混合物加入至一定量的水中,使得总量为100重量%。得到的制剂为均匀的乳剂。在使用之前,乳剂可以用水进一步稀释。
v)悬浮剂和悬浮浓缩剂
v-1)水基(SC、FS)
在合适的研磨装置中,例如在搅拌球磨机中,将20至60重量%的至少一种本发明的化合物,在加入2至10重量%的表面活性剂(例如木质素磺酸钠和聚氧乙烯脂肪醇醚)、0.1至2重量%的增稠剂(例如黄原胶)和水的情况下粉碎,得到活性化合物的微细悬浮剂。加入水的量使得总量为100重量%。用水稀释得到活性物质的稳定悬浮剂。对于FS型制剂,最多添加40%重量的粘合剂(例如聚乙烯醇)。
v-2)油基(OD、OF)
在合适的研磨装置中,例如在搅拌球磨机中,将20至60重量%的至少一种本发明的化合物,在加入2至10重量%的表面活性剂(例如木质素磺酸钠和聚氧乙烯脂肪醇醚)、0.1至2重量%的增稠剂(例如改性粘土,特别是膨润土或二氧化硅)和有机载体的情况下粉碎,得到活性物质的微细油悬浮剂。有机载体以使得总量为100重量%的量加入。用水稀释得到活性化合物的稳定分散体。
vi)水分散粒剂和水溶性粒剂(WG、SG)
将1至90重量%、优选20至80重量%、最优选50至80重量%的至少一种本发明的化合物在加入表面活性剂(例如木质素磺酸钠和烷基萘磺酸钠)和任选的载体材料的情况下精细研磨并通过典型的工业工艺(如挤出、喷雾干燥、流化床造粒)转化为水分散性或水溶性粒剂。表面活性剂和载体材料以使得总量达到100重量%的量使用。用水稀释得到活性物质的稳定分散体或溶液。
vii)水分散性粉末剂和水溶性粉末剂(WP、SP、WS)
将50至80重量%的至少一种本发明的化合物在加入1至20重量%的表面活性剂(例如木质素磺酸钠、烷基萘磺酸钠)和一定量的固体载体(例如硅胶)的情况下在转子/定子研磨机中研磨,固体载体的加入量使得总量为100重量%。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至25重量%的至少一种本发明化合物,在加入3至10重量%的表面活性剂(例如木质素磺酸钠)、1至5重量%的粘合剂(例如羧甲基纤维素)和使得总量为100重量%的水的情况下粉碎。得到活性物质的精细悬浮剂。用水稀释得到活性物质的稳定悬浮剂。
ix)微乳液(ME)
将5至20重量%的至少一种本发明的化合物加入至5至30重量%的有机溶剂混合物(例如脂肪酸二甲基酰胺和环己酮)、10至25重量%的表面活性剂混合物(例如聚氧乙烯脂肪醇醚和芳基苯酚乙氧基化物)和一定量的水中,使得其总量为100重量%。将该混合物搅拌1小时,以自发形成热力学稳定的微乳液。
x)微胶囊(CS)
油相包含5至50重量%的至少一种本发明的化合物、0至40重量%的水不溶性有机溶剂(例如芳烃)、2至15重量%的丙烯酸单体(例如甲基丙烯酸甲酯、甲基丙烯酸和二或三丙烯酸酯)分散在保护胶体(例如聚乙烯醇)的水溶液中。用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,油相包含5至50重量%的至少一种本发明的化合物、0至40重量%的水不溶性有机溶剂(例如芳烃)和异氰酸酯单体(例如二苯基甲烷4,4'-二异氰酸酯),将所述油相分散在保护胶体(例如聚乙烯醇)的水溶液中,这导致聚脲微胶囊的形成。任选地,添加多胺(例如六亚甲基二胺)用以导致聚脲微胶囊的形成。单体占总CS制剂的1至10重量%。
xi)可撒粉粉剂(DP、DS)
将1至10重量%的至少一种本发明的化合物精细研磨并与一定量的固体载体(例如精细研磨的高岭土)充分混合,使得总量为100重量%。
xii)颗粒剂(GR、FG)
0.5至30重量%的至少一种本发明的化合物被精细研磨并与一定量的固体载体(例如硅酸盐)结合,使得总量为100重量%。
xiii)超低容量液体(UL)
将1至50重量%的至少一种本发明的化合物溶解于一定量的有机溶剂(例如芳烃)中,使得其总量为100重量%。
制剂类型i)至xiii)可任选地包含其他助剂,例如0.1至1重量%的防腐剂、0.1至1重量%的消泡剂、0.1至1重量%的染料和/或颜料和5至10重量%的防冻剂。
混合物
式(I)的化合物还可与一种或多种合适的以下物质混合使用:杀真菌剂、杀细菌剂、杀螨剂、杀软体动物剂、杀线虫剂、杀昆虫剂、微生物剂、有益物种、除草剂、肥料、驱鸟剂、植物性毒素、止繁殖剂、安全剂、化学信息素和/或植物生长调节剂,从而例如拓宽作用谱、延长作用时间、提高作用速率、防止排斥或防止抗性发展。另外,这类活性化合物组合物可以改善植物生长和/或对非生物因素的耐受性,如对高温或低温、对干旱或对高水含量或土壤盐度的耐受性。还可改善开花和结果性能、优化发芽能力和根系发育、促进采收和提高产量、影响熟化、改善采收产品的品质和/或营养价值、延长储存期和/或改善采收产品的可加工性。
此外,式(I)的化合物可与其他活性化合物或化学信息素如引诱剂和/或驱鸟剂和/或植物活化剂和/或生长调节剂和/或肥料混合存在。同样地,式(I)的化合物可用于改善植物性能,如采收物的生长、产量和品质。
在本发明的一个具体的实施方案中,式(I)的化合物与其他化合物(优选下文所述的那些化合物)混合存在于制剂或由这些制剂制备的使用形式中。
如果下文提到的化合物之一可以以不同的互变异构形式存在,则这些形式也被包括在内,即使在各种情况下没有被明确提及。此外,所有被指出的混合配对剂可以——如果它们的官能团能够形成盐的话——任选地与合适的碱或酸形成盐。
杀昆虫剂/杀螨剂/杀线虫剂
本文中以其通用名称描述的活性化合物是已知的,并且记载于例如《农药手册》(“The Pesticide Manual”第16版,British Crop Protection Council 2012)中,或者可以在互联网(例如http://www.alanwood.net/pesticides)上找到。该分类基于在提交本专利申请时现行的IRAC作用方式分类方案。
(1)乙酰胆碱酯酶(AChE)抑制剂,优选氨基甲酸酯类,选自棉铃威(alanycarb)、涕灭威(aldicarb)、噁虫威(bendiocarb)、丙硫克百威(benfuracarb)、丁酮威(butocarboxim)、丁酮砜威(butoxycarboxim)、胺甲萘(carbaryl)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)、乙硫苯威(ethiofencarb)、仲丁威(fenobucarb)、伐虫脒(formetanate)、呋线威(furathiocarb)、异丙威(isoprocarb)、灭虫威(methiocarb)、灭多虫(methomyl)、速灭威(metolcarb)、杀线威(oxamyl)、抗蚜威(pirimicarb)、残杀威(propoxur)、硫双威(thiodicarb)、久效威(thiofanox)、唑蚜威(triazamate)、混杀威(trimethacarb)、灭除威(XMC)和灭杀威(xylylcarb);或有机磷酸酯类,选自乙酰甲胺磷(acephate)、甲基吡噁磷(azamethiphos)、乙基谷硫磷(azinphos-ethyl)、甲基谷硫磷(azinphos-methyl)、硫线磷(cadusafos)、氯氧磷(chlorethoxyfos)、毒虫畏(chlorfenvinphos)、氯甲硫磷(chlormephos)、甲基毒死蜱(chloropyrifos-methyl)、蝇毒磷(coumaphos)、杀螟腈(cyanophos)、甲基内吸磷(demeton-S-methyl)、二嗪农(diazinon)、敌敌畏(dichlorvos/DDVP)、百治磷(dicrotophos)、乐果(dimethoate)、甲基毒虫畏(dimethylvinphos)、乙拌磷(disulfoton)、苯硫磷(EPN)、乙硫磷(ethion)、灭线磷(ethoprophos)、伐灭磷(famphur)、苯线磷(fenamiphos)、杀螟松(fenitrothion)、倍硫磷(fenthion)、噻唑磷(fosthiazate)、庚烯磷(heptenophos)、氰咪唑硫磷(imicyafos)、异柳磷(isofenphos)、O-(甲氧基氨基硫代磷酰基)水杨酸异丙酯、异噁唑磷(isoxathion)、马拉硫磷(malathion)、灭蚜磷(mecarbam)、甲胺磷(methamidophos)、杀扑磷(methidathion)、速灭磷(mevinphos)、久效磷(monocrotophos)、二溴磷(naled)、氧乐果(omethoate)、亚砜磷(oxydemeton-methyl)、对硫磷甲酯(parathion-methyl)、稻丰散(phenthoate)、甲拌磷(phorate)、伏杀磷(phosalone)、亚胺硫磷(phosmet)、磷胺(phosphamidon)、肟硫磷(phoxim)、甲基吡啶磷(pirimiphos-methyl)、丙溴磷(profenofos)、胺丙畏(propetamphos)、丙硫磷(prothiofos)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、喹硫磷(quinalphos)、治螟磷(sulfotep)、丁基吡啶磷(tebupirimfos)、双硫磷(temephos)、特丁硫磷(terbufos)、杀虫畏(tetrachlorvinphos)、甲基乙拌磷(thiometon)、三唑磷(triazophos)、敌百虫(triclorfon)和蚜灭磷(vamidothion)。
(2)GABA-门控氯化物通道阻断剂,优选环戊二烯有机氯类,选自氯丹(chlordane)和硫丹(endosulfan);或苯基吡唑类(fiproles),例如乙虫腈(ethiprole)和氟虫腈(fipronil)。
(3)钠通道调节剂,优选拟除虫菊酯类(pyrethroid),选自氟丙菊酯(acrinathrin)、丙烯除虫菊酯(allethrin)、d-顺式-反式丙烯除虫菊酯(d-cis-transallethrin)、d-反式丙烯除虫菊酯(d-trans allethrin)、联苯菊酯(bifenthrin)、生物烯丙菊酯(bioallethrin)、生物烯丙菊酯s-环戊烯基异构体(bioallethrin s-cyclopentenyl isomer)、生物苄呋菊酯(bioresmethrin)、乙氰菊酯(cycloprothrin)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、氯氟氰菊酯(cyhalothrin)、λ-氯氟氰菊酯(lambda-cyhalothrin)、γ-氯氟氰菊酯(gamma-cyhalothrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、β-氯氰菊酯(beta-cypermethrin)、θ-氯氰菊酯(theta-cypermethrin)、ζ-氯氰菊酯(zeta-cypermethrin)、苯醚氰菊酯[(1R)-反式异构体](cyphenothrin[(1R)-trans-isomer])、溴氰菊酯(deltamethrin)、右旋烯炔菊酯[(EZ)-(1R)-异构体](empenthrin[(EZ)-(1R)-isomer])、高氰戊菊酯(esfenvalerate)、醚菊酯(etofenprox)、甲氰菊酯(fenpropathrin)、氰戊菊酯(fenvalerate)、氟氰戊菊酯(flucythrinate)、氟氯苯菊酯(flumethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、苄螨醚(halfenprox)、炔咪菊酯(imiprothrin)、噻嗯菊酯(kadethrin)、甲氧苄氟菊酯(momfluorothrin)、苄氯菊酯(permethrin)、苯醚菊酯[(1R)-反式异构体](phenothrin[(1R)-trans-isomer])、炔丙菊酯(prallethrin)、除虫菊酯(pyrethrine、pyrethrum)、苄呋菊酯(resmethrin)、氟硅菊酯(silafluofen)、七氟菊酯(tefluthrin)、胺菊酯(tetramethrin)、胺菊酯[(1R)-异构体](tetramethrin[(1R)-isomer])、四溴菊酯(tralomethrin)和四氟苯菊酯(transfluthrin);或DDT;或甲氧氯。
(4)烟碱乙酰胆碱受体(nAChR)竞争调节剂,优选新烟碱类(neonicotinoids),选自啶虫脒(acetamiprid)、噻虫胺(clothianidin)、呋虫胺(dinotefuran)、吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、噻虫啉(thiacloprid)和噻虫嗪(thiamethoxam)或尼古丁(nicotine)或选自氟啶虫胺腈(sulfoxaflor)的亚砜亚胺类(sulfoximines);或选自氟吡呋喃酮(flupyradifurone)的丁烯酸内酯类(butenolids),或选自三氟苯嘧啶(triflumezopyrim)的介离子物(mesoionics)。
(5)烟碱乙酰胆碱受体(nAChR)变构调节剂(位点I),优选多杀菌素类(spinosyns),选自乙基多杀菌素(spinetoram)和多杀菌素(spinosad)。
(6)谷氨酸门控氯化物通道(GluCl)变构调节剂,优选阿凡曼维菌素类/米尔倍霉素类(avermectins/milbemycins),选自阿巴克丁(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、雷皮菌素(lepimectin)和灭螨菌素(milbemectin)。
(7)保幼激素模仿物,优选保幼激素类似物,选自烯虫乙酯(hydroprene)、烯虫炔酯(kinoprene)和烯虫酯(methoprene)或苯氧威(fenoxycarb)或蚊蝇醚(pyriproxyfen)。
(8)各种非特异性(多位点)抑制剂,优选烷基卤化物,选自甲基溴化物和其他烷基卤化物;或氯化苦(chloropicrine)或硫酰氟或硼砂或吐酒石(tartar emetic)或异氰酸甲酯生成剂,选自棉隆(diazomet)或威百亩(metam)。
(9)弦音器官TRPV通道调节剂,优选选自吡蚜酮(pymetrozine)和氟虫吡喹(pyrifluquinazone)的吡啶偶氮甲烷(pyridine azomethane),或选自双丙环虫酯(Afidopyropen)的pyropene。
(10)影响CHS1的螨生长抑制剂,选自四螨嗪(clofentezine)、噻螨酮(hexythiazox)和氟螨嗪(diflovidazin)或乙螨唑(etoxazole)。
(11)昆虫肠膜的微生物干扰剂,选自苏云金芽孢杆菌以色列亚种(Bacillusthuringiensis subspecies israelensis)、球形芽孢杆菌(Bacillus sphaericus)、苏云金芽胞杆菌鲇泽亚种(Bacillus thuringiensis subspecies aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis subspecies kurstaki)、苏云金芽孢杆菌拟步行甲亚种(Bacillus thuringiensis subspecies tenebrionis)和B.t.植物蛋白,选自Cry1Ab、Cry1Ac、Cry1Fa、Cry1A.105、Cry2Ab、Vip3A、mCry3A、Cry3Ab、Cry3Bb和Cry34Ab1/35Ab1。
(12)线粒体ATP合成酶的抑制剂,优选ATP干扰剂,选自丁醚脲(diafenthiuron)或有机锡化合物,其选自三唑锡(azocyclotin)、三环锡(cyhexatin)和苯丁锡(fenbutatinoxide),或克螨特(propargite)或四氯杀螨砜(tetradifon)。
(13)通过阻断质子梯度的氧化磷酸化的解偶联剂,选自虫螨腈(chlorfenapyr)、二硝甲酚(DNOC)和氟虫胺(sulphluramid)。
(14)烟碱乙酰胆碱受体通道阻断剂,选自杀虫磺(bensultap)、杀螟丹氢氯化物(cartap hydrochloride)、杀虫环(thiocyclam)和杀虫双(thiosultap-sodium)。
(15)几丁质生物合成抑制剂,其影响CHS1,优选选自双三氟虫脲(bistrifluron)、定虫隆(chlofluazuron)、二氟苯隆(diflubenzuron)、氟环脲(flucycloxuron)、氟虫脲(flufenoxuron)、氟铃脲(hexaflumuron)、氯芬奴隆(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、氟苯脲(teflubenzuron)和杀铃脲(triflumuron)的苯甲酰脲(benzoylurea)类。
(16)几丁质生物合成抑制剂,1型,选自噻嗪酮(buprofezin)。
(17)蜕皮干扰剂(特别是对于双翅目(Diptera),即双翅昆虫(dipteran)),选自灭蝇胺(cyromazine)。
(18)蜕皮激素受体激动剂,优选选自环虫酰胺(chromafenozide)、氯虫酰肼(halofenozide)、甲氧虫酰肼(methoxyfenozide)和虫酰肼(tebufenozide)的二酰基肼(diacylhydrazine)类。
(19)章鱼胺受体激动剂,选自双甲脒(amitraz)。
(20)线粒体复合物III电子传递抑制剂,选自氟蚁腙(hydramethylnone)、灭螨醌(acequinocyl)、嘧螨酯(fluacrypyrim)和联苯肼酯(bifenazate)。
(21)线粒体复合物I电子传递抑制剂,优选METI杀螨剂和杀昆虫剂,选自喹螨醚(fenazaquin)、唑螨酯(fenpyroximate)、嘧螨醚(pyrimidifen)、哒螨灵(pyridaben)、吡螨胺(tebufenpyrad)和唑虫酰胺(tolfenpyrad);或鱼藤酮(rotenone)(鱼藤属(Derris))。
(22)电压依赖型钠通道阻断剂,优选选自茚虫威(indoxacarb)的噁二嗪(oxadiazine)类和选自氰氟虫腙(metaflumizone)的缩氨脲(semicarbazone)。
(23)乙酰基CoA羧化酶的抑制剂,优选特窗酸(tetronic acid)和特特拉姆酸(tetramic acid)衍生物,选自螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、甲氧哌啶乙酯(spiropidion)和螺虫乙酯(spirotetramat)。
(24)线粒体复合物IV电子传递抑制剂,优选选自磷化铝、磷化钙、膦和磷化锌的磷化物,或选自氰化钙、氰化钾和氰化钠的氰化物。
(25)线粒体复合物II电子传递抑制剂,优选β-酮腈衍生物,选自腈吡螨酯(cyenopyrafen)和丁氟螨酯(cyflumetofen)或选自pyflubumide的甲酰苯胺,。
(28)鱼尼丁受体调节剂,优选二酰胺类,选自氯虫苯甲酰胺(chlorantraniliprole)、溴氰虫酰胺(cyantraniliprole)、环溴虫酰胺(cyclaniliprole)、氟虫双酰胺(flubendiamide)和氟氰虫酰胺(tetraniliprole);
(29)弦音器官调节剂(具有未定义的靶位点),选自氟啶虫酰胺(flonicamid)。
(30)GABA门控氯化物通道变构调节剂,优选选自溴氟苯胺(broflanilide)的间二酰胺或选自fluxametamide的异噁唑。
(31)杆状病毒,优选选自苹果蠹蛾(Cydia pomonella GV)和Thaumatotibialeucotreta(GV)的颗粒病毒(GV)或选自Anticarsia gemmatalis MNPV、Flucypyriprole和Helicoverpa armigera NPV的核型多角体病毒(NPV)。
(32)烟碱型乙酰胆碱受体的变构调节剂(位点II),其选自GS-ω/κ-HXTX-Hv1a肽。
(33)其他活性成分,选自:Acynonapyr、阿福拉纳(Afoxolaner)、印楝素(Azadirachtin)、Benclothiaz、苯螨特(Benzoximate)、Benzpyrimoxan、溴螨酯(Bromopropylate)、灭螨猛(Chinomethionat)、氯丙炔菊酯(Chloroprallethrin)、冰晶石(Cryolite)、Cyclobutrifluram、环氧虫啶(Cycloxaprid)、Cyetpyrafen、氯氟氰虫酰胺(Cyhalodiamide)、Cyproflanilide(CAS2375110-88-4)、Dicloromezotiaz、三氯杀螨醇(Dicofol)、Dimpropyridaz、ε-甲氧苄氟菊酯(epsilon-Metofluthrin)、ε-Momfluthrin、Flometoquin、Fluazaindolizine、Flucypyriprole(CAS1771741-86-6)、联氟砜(Fluensulfone)、嘧虫胺(Flufenerim)、氟菌螨酯(Flufenoxystrobin)、丁虫腈(Flufiprole)、Fluhexafon、氟吡菌酰胺(Fluopyram)、Flupyrimin、氟雷拉纳(Fluralaner)、呋喃虫酰肼(Fufenozide)、Flupentiofenox、戊吡虫胍(Guadipyr)、Heptafluthrin、氯噻啉(Imidaclothiz)、异菌脲(Iprodione)、Isocycloseram、κ-联苯菊酯(kappa-Bifenthrin)、κ-七氟菊酯(kappa-Tefluthrin)、Lotilaner、氯氟醚菊酯(Meperfluthrin)、Nicofluprole(CAS1771741-86-6)、Oxazosulfyl、哌虫啶(Paichongding)、啶虫丙醚(Pyridalyl)、Pyrifluquinazon、嘧螨胺(Pyriminostrobin)、Sarolaner、Spidoxamat、Spirobudiclofen、四氟醚菊酯(Tetramethylfluthrin)、四氯虫酰胺(Tetrachlorantraniliprole)、Tigolaner、Tioxazafen、硫氟肟醚(Thiofluoximate)、Tyclopyrazoflor、碘甲烷;以及基于坚强芽孢杆菌(Bacillus firmus)(I-1582,Votivo)和印楝素(azadirachtin)(BioNeem)的制剂,以及以下化合物:1-{2-氟-4-甲基-5-[(2,2,2-三氟乙基)亚磺酰基]苯基}-3-(三氟甲基)-1H-1,2,4-三唑-5-胺(由WO2006/043635已知)(CAS 885026-50-6)、2-氯-N-[2-{1-[(2E)-3-(4-氯苯基)丙-2-烯-1-基]哌啶-4-基}-4-(三氟甲基)苯基]异烟酰胺(由WO2006/003494已知)(CAS 872999-66-1)、3-(4-氯-2,6-二甲基苯基)-4-羟基-8-甲氧基-1,8-二氮杂螺[4.5]癸-3-烯-2-酮(由WO 2010052161已知)(CAS1225292-17-0)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基乙基碳酸酯(由EP2647626已知)(CAS1440516-42-6)、PF1364(由JP2010/018586已知)(CAS1204776-60-2)、(3E)-3-[1-[(6-氯-3-吡啶基)甲基]-2-吡啶亚基]-1,1,1-三氟-丙-2-酮(由WO2013/144213已知)(CAS 1461743-15-6)、N-[3-(苄基氨基甲酰基)-4-氯苯基]-1-甲基-3-(五氟乙基)-4-(三氟甲基)-1H-吡唑-5-甲酰胺(由WO2010/051926已知)(CAS 1226889-14-0)、5-溴-4-氯-N-[4-氯-2-甲基-6-(甲基氨基甲酰基)苯基]-2-(3-氯-2-吡啶基)吡唑-3-甲酰胺(由CN103232431已知)(CAS 1449220-44-3)、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧代-3-硫杂环丁基)-苯甲酰胺、4-[5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(反式-1-氧代-3-硫杂环丁基)-苯甲酰胺和4-[(5S)-5-(3,5-二氯苯基)-4,5-二氢-5-(三氟甲基)-3-异噁唑基]-2-甲基-N-(顺式-1-氧代-3-硫杂环丁基)苯甲酰胺(由WO 2013/050317A1已知)(CAS1332628-83-7)、N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]-丙酰胺、(+)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]-丙酰胺和(-)-N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)亚磺酰基]-丙酰胺(由WO 2013/162715 A2、WO 2013/162716 A2、US2014/0213448A1已知)(CAS1477923-37-7)、5-[[(2E)-3-氯-2-丙烯-1-基]氨基]-1-[2,6-二氯-4-(三氟甲基)苯基]-4-[(三氟甲基)亚磺酰基]-1H-吡唑-3-甲腈(由CN101337937 A已知)(CAS1105672-77-2)、3-溴-N-[4-氯-2-甲基-6-[(甲基氨基)硫代甲基]苯基]-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(Liudaibenjiaxuanan,由CN 103109816 A已知)(CAS1232543-85-9);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-甲酰胺(由WO 2012/034403A1已知)(CAS1268277-22-0)、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-甲酰胺(由WO 2011/085575 A1已知)(CAS1233882-22-8)、4-[3-[2,6-二氯-4-[(3,3-二氯-2-丙烯-1-基)氧基]苯氧基]丙氧基]-2-甲氧基-6-(三氟甲基)-嘧啶(由CN 101337940 A已知)(CAS1108184-52-6);(2E)-和2(Z)-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]-肼甲酰胺(由CN 101715774 A已知)(CAS1232543-85-9);3-(2,2-二氯乙烯基)-2,2-二甲基-4-(1H-苯并咪唑-2-基)苯基环丙烷甲酸酯(由CN 103524422 A已知)(CAS1542271-46-4);(4aS)-7-氯-2,5-二氢-2-[[(甲氧基羰基)[4-[(三氟甲基)硫基]苯基]氨基]羰基]-茚并[1,2-e][1,3,4]噁二嗪-4a(3H)-甲酸甲酯(由CN 102391261 A已知)(CAS 1370358-69-2);6-脱氧-3-O-乙基-2,4-二-O-甲基-1-[N-[4-[1-[4-(1,1,2,2,2-五氟乙氧基)苯基]-1H-1,2,4-三唑-3-基]苯基]氨基甲酸酯]-α-L-吡喃甘露糖(由US2014/0275503 A1已知)(CAS1181213-14-8);8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基-哒嗪-3-基)-3-氮杂双环[3.2.1]辛烷(CAS1253850-56-4)、(8-反式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂双环[3.2.1]辛烷(CAS933798-27-7)、(8-顺式)-8-(2-环丙基甲氧基-4-三氟甲基苯氧基)-3-(6-三氟甲基哒嗪-3-基)-3-氮杂双环[3.2.1]辛烷(由WO2007040280 A1、WO 2007040282A1已知)(CAS 934001-66-8)、N-[4-(氨基硫代甲基)-2-甲基-6-[(甲基氨基)羰基]苯基]-3-溴-1-(3-氯-2-吡啶基)-1H-吡唑-5-甲酰胺(由CN103265527 A已知)(CAS1452877-50-7)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-1,8-二氮杂螺[4.5]癸烷-2,4-二酮(由WO 2014/187846A1已知)(CAS1638765-58-8)、3-(4-氯-2,6-二甲基苯基)-8-甲氧基-1-甲基-2-氧代-1,8-二氮杂螺[4.5]癸-3-烯-4-基碳酸乙酯(由WO 2010/066780A1,WO 2011151146 A1已知)(CAS1229023-00-0)、N-[1-(2,6-二氟苯基)-1H-吡唑-3-基]-2-(三氟甲基)苯甲酰胺(由WO 2014/053450A1已知)(CAS1594624-87-9)、N-[2-(2,6-二氟苯基)-2H-1,2,3-三唑-4-基]-2-(三氟甲基)苯甲酰胺(由WO 2014/053450 A1已知)(CAS1594637-65-6)、N-[1-(3,5-二氟-2-吡啶)-1H-吡唑-3-基]-2-(三氟甲基)苯甲酰胺(由WO 2014/053450 A1已知)(CAS 1594626-19-3)、(3R)-3-(2-氯-5-噻唑)-2,3-二氢-8-甲基-5,7-二氧杂-6-苯基-5H-噻唑并[3,2-a]嘧啶内盐(由WO 2018/177970 A1已知)(CAS 2246757-58-2);3-(2-氯-5-噻唑基)-2,3-二氢-8-甲基-5,7-二氧杂-6-苯基-5H-噻唑并[3,2-a]嘧啶内盐(由WO 2018/177970 A1已知)(CAS 2246757-56-0);N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-2-(甲磺酰基)丙酰胺(由WO 2019/236274 A1已知)(CAS2396747-83-2);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-3-[(4-氟苯甲酰基)氨基]苯甲酰胺(由WO 2019059412 A1已知)(CAS1207977-87-4);3-溴-1-(3-氯-2-吡啶基)-N-[4,6-二氯-3-氟-2-[(甲基氨基)羰基]苯基]-1H-吡唑-5-甲酰胺(氟氯二酰胺;由CN110835330 A、CN106977494A已知)(CAS:2129147-03-9)。
杀线虫剂
本文中以其通用名称描述的活性化合物是已知的,并且记载于例如《农药手册》(“The Pesticide Manual”第16版,British Crop Protection Council 2012)中,或者可以在互联网(例如http://www.alanwood.net/pesticides)上找到。该分类基于在提交本专利申请时现行的IRAC作用方式分类方案。
(方案N-1)乙酰胆碱酯酶(AChE)抑制剂,优选氨基甲酸酯类(N-1A),选自涕灭威(aldicarb)、丙硫克百威(benfuracarb)、虫螨威(carbofuran)、丁硫克百威(carbosulfan)和硫双威(thiodicarb);或有机磷酸酯类(N-1B),选自硫线磷(cadusafos)、灭线磷(ethoprofos)、苯线磷(fenamiphos)、噻唑磷(fosthiazate)、氰咪唑硫磷(imicyafos)、甲拌磷(phorate)和特丁硫磷(terbufos)。
(方案N-2)谷氨酸门控氯化物通道(GluCl)变构调节剂,优选阿凡曼维菌素类(avermectins),选自阿巴克丁(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectinbenzoate)。
(方案N-3)线粒体复合物II电子传递抑制剂,尤其是琥珀酸辅酶Q还原酶的抑制剂,优选选自氟吡菌酰胺(Fluopyram)的吡啶基甲基苯甲酰胺。
(方案N-4)脂质合成/生长调节调节剂,尤其是乙酰基CoA羧化酶的抑制剂,优选选自螺虫乙酯(spirotetramat)的特窗酸和特特拉姆酸。
(方案N-UN)具有各种化学性质的作用方式未知或不确定的化合物,选自氟噻虫砜(fluensulfone)、三氟咪啶酰胺(fluazaindolizine)、糠醛(furfural)、异菌脲(iprodione)和tioxazafen。
(方案N-UNX)作用方式未知或不确定的化合物:推测的多位点抑制剂,优选选自二硫化碳和二甲基二硫(DMDS)的挥发性硫生成剂,或选自四硫代碳酸钠的二硫化碳释放剂,或选自甲基溴化物和甲基碘化物(碘甲烷)的烷基卤化物,或选自以下的卤代烃:1,2-二溴-3-氯丙烷(DBCP)和1,3-二氯丙烯的卤代烃,或氯化苦(Chloropicrin),或选自异硫氰酸烯丙酯(allyl isothiocyanate)、diazomet、N-甲基二硫代氨基甲酸钾(metam potassium)和N-甲基二硫代氨基甲酸钠(metam sodium)的异硫氰酸甲盐生成剂。
(方案N-UNB)作用方式未知或不确定的细菌剂(非Bt),优选细菌或细菌衍生的,选自伯霍尔德杆菌属(Burkholderia spp.),例如rinojensis A396;芽孢杆菌属(Bacillusspp.),例如坚强芽孢杆菌(firmus)、地衣芽孢杆菌(licheniformis)、解淀粉芽孢杆菌(amyloliquefaciens)或枯草芽孢杆菌(subtilis);巴斯德氏芽菌属(Pasteuria spp.),例如穿刺巴氏杆菌(penetrans)或nishizawae;假单胞菌属(Pseudomonas spp.),例如绿针假单胞菌(chlororaphis)或荧光假单胞菌(fluorescens)和链霉菌属(Streptomyces spp.),例如利迪链霉菌(lydicus)、dicklowii或albogriseolus。
(方案N-UNF)作用方式未知或不确定的真菌剂,优选真菌或真菌衍生的,选自放线菌属(Actinomyces spp.)、例如链球菌(streptococcus);线虫捕足菌属(Arthrobotrysspp.),例如oligospora;曲霉属(Aspergillus spp.),例如黑曲霉(niger);产气菌属(Muscodor spp.),例如白色产气菌属(albus);漆斑菌属(Myrothecium spp.),例如疣孢漆斑菌(verrucaria);拟青霉属(Paecilomyces spp.),例如淡紫拟青霉(lilacinus(Purpureocillium lilacinum))、肉色拟青霉(carneus)或玫烟色拟青霉(fumosoroseus);厚垣普奇尼亚菌属(Pochonia spp.),例如chlamydosporia,和木霉属(Trichodermaspp.),例如哈次木霉(harzianum)、virens、atroviride或viride。
(方案N-UNE)作用方式未知或不确定的植物或动物来源的试剂,包括合成提取物和未精炼的油,优选选自印苦楝子素(azadirachtin)、山茶籽饼(camellia seed cake)、精油、大蒜提取物、卡兰贾油(pongamia oil)、萜烯(terpenes),例如香芹酚(carvacrol)和皂树(Quillaja saponaria)提取物的植物或动物来源的试剂。
杀真菌剂
本文通过其通用名称提及的活性成分是已知的,并且例如记载于《农药手册》(第16版,British Crop Protection Council)中或可在互联网(例如:www.alanwood.net/pesticides)上检索到。
(1)至(15)类的所有命名的杀真菌混合配对剂——如果它们的官能团能够形成盐的话——可任选地与合适的碱或酸形成盐。(1)至(15)类的所有命名的混合配对剂在适用的情况下可包括互变异构形式。
1)麦角甾醇生物合成抑制剂,例如(1.001)环丙唑醇(cyproconazole)、(1.002)苯醚甲环唑(difenoconazole)、(1.003)氟环唑(epoxiconazole)、(1.004)腈苯唑(fenbuconazole)、(1.005)环酰菌胺(fenhexamid)、(1.006)苯锈啶(fenpropidin)、(1.007)丁苯吗啉(fenpropimorph)、(1.008)胺苯吡菌酮(fenpyrazamine)、(1.009)氟喹唑(fluquinconazole)、(1.010)粉唑醇(flutriafol)、(1.011)己唑醇(hexaconazole)、(1.012)烯菌灵(imazalil)、(1.013)烯菌灵硫酸盐(imazalil sulfate)、(1.014)种菌唑(ipconazole)、(1.015)ipfentrifluconazole、(1.016)氯氟醚菌唑(mefentrifluconazole)、(1.017)叶菌唑(metconazole)、(1.018)腈菌唑(myclobutanil)、(1.019)多效唑(paclobutrazol)、(1.020)戊菌唑(penconazole)、(1.021)咪鲜胺(prochloraz)、(1.022)丙环唑(propiconazole)、(1.023)丙硫菌唑(prothioconazole)、(1.024)氯啶菌酯(pyrisoxazole)、(1.025)螺环菌胺(spiroxamine)、(1.026)戊唑醇(tebuconazole)、(1.027)氟醚唑(tetraconazole)、(1.028)三唑醇(triadimenol)、(1.029)克啉菌(tridemorph)、(1.030)灭菌唑(triticonazole)、(1.031)(1R,2S,5S)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.032)(1S,2R,5R)-5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环戊醇、(1.033)(2R)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.034)(2R)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.035)(2R)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.036)(2S)-2-(1-氯环丙基)-4-[(1R)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.037)(2S)-2-(1-氯环丙基)-4-[(1S)-2,2-二氯环丙基]-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(1.038)(2S)-2-[4-(4-氯苯氧基)-2-(三氟甲基)苯基]-1-(1H-1,2,4-三唑-1-基)丙-2-醇、(1.039)(R)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.040)(S)-[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.041)[3-(4-氯-2-氟苯基)-5-(2,4-二氟苯基)-1,2-唑-4-基](吡啶-3-基)甲醇、(1.042)1-({(2R,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.043)1-({(2S,4S)-2-[2-氯-4-(4-氯苯氧基)苯基]-4-甲基-1,3-二氧戊环-2-基}甲基)-1H-1,2,4-三唑、(1.044)1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.045)1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.046)1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑-5-基硫氰酸酯、(1.047)2-[(2R,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.048)2-[(2R,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.049)2-[(2R,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.050)2-[(2R,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.051)2-[(2S,4R,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.052)2-[(2S,4R,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.053)2-[(2S,4S,5R)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.054)2-[(2S,4S,5S)-1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.055)2-[1-(2,4-二氯苯基)-5-羟基-2,6,6-三甲基庚-4-基]-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.056)2-[6-(4-溴苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇、(1.057)2-[6-(4-氯苯氧基)-2-(三氟甲基)-3-吡啶基]-1-(1,2,4-三唑-1-基)丙-2-醇、(1.058)2-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.059)2-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.060)2-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟苯基)-环氧乙烷-2-基]甲基}-2,4-二氢-3H-1,2,4-三唑-3-硫酮、(1.061)3-[2-(1-氯环丙基)-3-(3-氯-2-氟-苯基)-2-羟基-丙基]咪唑-4-腈、(1.062)4-[[6-[rac-(2R)-2-(2,4-二氟苯基)-1,1-二氟-2-羟基-3-(5-硫代-4H-1,2,4-三唑-1-基)丙基]-3-吡啶基]氧基]-苯基腈、(1.063)5-(4-氯苄基)-2-(氯甲基)-2-甲基-1-(1H-1,2,4-三唑-1-基甲基)环-戊醇、(1.064)5-(烯丙基硫烷基)-1-{[3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.065)5-(烯丙基硫烷基)-1-{[rel(2R,3R)-3-(2-氯苯基)-2-(2,4-二氟苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.066)5-(烯丙基硫烷基)-1-{[rel(2R,3S)-3-(2-氯苯基)-2-(2,4-二氟-苯基)环氧乙烷-2-基]甲基}-1H-1,2,4-三唑、(1.067)2-[2-氯-4-(4-氯苯氧基)苯基]-2-羟基-3-(1H-1,2,4-三唑-1-基)丙酸甲酯、(1.068)N'-(2-氯-5-甲基-4-苯氧基苯基)-N-乙基-N-甲基亚氨基甲酰胺、(1.069)N'-[2-氯-4-(2-氟苯氧基)-5-甲基苯基]-N-乙基-N-甲基亚氨基甲酰胺、(1.070)N'-[5-溴-6-(2,3-二氢-1H-茚-2-基氧基)-2-甲基吡啶-3-基]-N-乙基-N-甲基亚氨基甲酰胺、(1.071)N'-{4-[(4,5-二氯-1,3-噻唑-2-基)氧基]-2,5-二甲基苯基}-N-乙基-N-甲基亚氨基甲酰胺、(1.072)N'-{5-溴-2-甲基-6-[(1-丙氧基丙-2-基)氧基]吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.073)N'-{5-溴-6-[(1R)-1-(3,5-二氟苯基)乙氧基]-2-甲基-吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.074)N'-{5-溴-6-[(1S)-1-(3,5-二氟苯基)-乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.075)N'-{5-溴-6-[(cis-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.076)N'-{5-溴-6-[(trans-4-异丙基环己基)氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.077)N'-{5-溴-6-[1-(3,5-二氟苯基)乙氧基]-2-甲基吡啶-3-基}-N-乙基-N-甲基亚氨基甲酰胺、(1.078)N-异丙基-N'-[5-甲氧基-2-甲基-4-(2,2,2-三氟-1-羟基-1-苯基乙基)苯基]-N-甲基亚氨基甲酰胺。
2)呼吸链复合物I或II的抑制剂,例如(2.001)苯并烯氟菌唑(benzovindiflupyr)、(2.002)联苯吡菌胺(bixafen)、(2.003)啶酰菌胺(boscalid)、(2.004)萎锈灵(carboxin)、(2.005)cyclobutrifluram、(2.006)flubeneteram、(2.007)fluindapyr、(2.008)氟吡菌酰胺(Fluopyram)、(2.009)氟酰胺(flutolanil)、(2.010)氟唑菌酰胺(fluxapyroxad)、(2.011)呋吡菌胺(furametpyr)、(2.012)inpyrfluxam、(2.013)噻吩酰菌酮(Isofetamid)、(2.014)isoflucypram、(2.015)吡唑萘菌胺(isopyrazam)、(2.016)氟唑菌苯胺(penflufen)、(2.017)吡噻菌胺(penthiopyrad)、(2.018)氟唑菌酰羟胺(pydiflumetofen)、(2.019)pyrapropoyne、(2.020)pyraziflumid、(2.021)氟唑环菌胺(sedaxane)、(2.022)1,3-二甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.023)1,3-二甲基-N-[(3R)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.024)1,3-二甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.025)1-甲基-3-(三氟甲基)-N-[2'-(三氟甲基)联苯基-2-基]-1H-吡唑-4-甲酰胺、(2.026)2-氟-6-(三氟甲基)-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)苯甲酰胺、(2.027)3-(二氟甲基)-1-甲基-N-(1,1,3-三甲基-2,3-二氢-1H-茚-4-基)-1H-吡唑-4-甲酰胺、(2.028)3-(二氟甲基)-1-甲基-N-[(3S)-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1H-吡唑-4-甲酰胺、(2.029)3-(二氟甲基)-N-[(3R)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.030)3-(二氟甲基)-N-[(3S)-7-氟-1,1,3-三甲基-2,3-二氢-1H-茚-4-基]-1-甲基-1H-吡唑-4-甲酰胺、(2.031)5,8-二氟-N-[2-(2-氟-4-{[4-(三氟甲基)吡啶-2-基]氧基}苯基)乙基]喹唑啉-4-胺、(2.032)N-[(1R,4S)-9-(二氯-亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.033)N-[(1S,4R)-9-(二氯亚甲基)-1,2,3,4-四氢-1,4-亚甲基萘-5-基]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.034)N-[1-(2,4-二氯苯基)-1-甲氧基丙-2-yl]-3-(二氟甲基)-1-甲基-1H-吡唑-4-甲酰胺、(2.035)N-[rac-(1S,2S)-2-(2,4-二氯苯基)环丁基]-2-(三氟甲基)烟酰胺。
3)呼吸链复合物III的抑制剂,例如(3.001)唑嘧菌胺(ametoctradin)、(3.002)安美速(amisulbrom)、(3.003)腈嘧菌酯(azoxystrobin)、(3.004)甲香菌酯(coumethoxystrobin)、(3.005)丁香菌酯(coumoxystrobin)、(3.006)氰霜唑(cyazofamid)、(3.007)醚菌胺(dimoxystrobin)、(3.008)烯肟菌酯(enoxastrobin)、(3.009)唑菌酮(famoxadone)、(3.010)咪唑菌酮(fenamidone)、(3.011)fenpicoxamid、(3.012)florylpicoxamid、(3.013)氟菌螨酯(flufenoxystrobin)、(3.014)氟嘧菌酯(fluoxastrobin)、(3.015)醚菌酯(kresoxim-甲基)、(3.016)mandestrobin、(3.017)苯氧菌胺(metominostrobin)、(3.018)metyltetraprole、(3.019)肟醚菌胺(orysastrobin)、(3.020)啶氧菌酯(picoxystrobin)、(3.021)唑菌胺酯(pyraclostrobin)、(3.022)唑胺菌酯(pyrametostrobin)、(3.023)唑胺菌酯(pyraoxystrobin)、(3.024)肟菌酯(trifloxystrobin)、(3.025)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-氟-2-苯基乙烯基]氧基}苯基)亚乙基]氨基}氧基)甲基]苯基}-2-(甲氧基亚氨基)-N-甲基乙酰胺、(3.026)(2E,3Z)-5-{[1-(4-氯苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.027)(2R)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.028)(2S)-2-{2-[(2,5-二甲基苯氧基)甲基]苯基}-2-甲氧基-N-甲基乙酰胺、(3.029)N-(3-乙基-3,5,5-三甲基环己基)-3-甲酰胺基-2-羟基苯甲酰胺、(3.030)(2E,3Z)-5-{[1-(4-氯-2-氟苯基)-1H-吡唑-3-基]氧基}-2-(甲氧基亚氨基)-N,3-二甲基戊-3-烯酰胺、(3.031){5-[3-(2,4-二甲基苯基)-1H-吡唑-1-基]-2-甲基苄基}氨基甲酸甲酯。
4)有丝分裂和细胞分裂抑制剂,例如(4.001)多菌灵(carbendazim)、(4.002)乙霉威(diethofencarb)、(4.003)噻唑菌胺(ethaboxam)、(4.004)氟吡菌胺(fluopicolide)、(4.005)fluopimomid、(4.006)苯菌酮(metrafenone)、(4.007)戊菌隆(pencycuron)、(4.008)pyridachlometyl、(4.009)pyriofenone(chlazafenone)、(4.010)噻苯咪唑(thiabendazole)、(4.011)甲基硫菌灵(thiophanate-甲基)、(4.012)苯酰菌胺(zoxamide)、(4.013)3-氯-5-(4-氯苯基)-4-(2,6-二氟苯基)-6-甲基哒嗪、(4.014)3-氯-5-(6-氯吡啶-3-基)-6-甲基-4-(2,4,6-三氟苯基)哒嗪、(4.015)4-(2-溴-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.016)4-(2-溴-4-氟苯基)-N-(2-溴-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.017)4-(2-溴-4-氟苯基)-N-(2-溴苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.018)4-(2-溴-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.019)4-(2-溴-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.020)4-(2-溴-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.021)4-(2-氯-4-氟苯基)-N-(2,6-二氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.022)4-(2-氯-4-氟苯基)-N-(2-氯-6-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.023)4-(2-氯-4-氟苯基)-N-(2-氯苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.024)4-(2-氯-4-氟苯基)-N-(2-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.025)4-(4-氯苯基)-5-(2,6-二氟苯基)-3,6-二甲基哒嗪、(4.026)N-(2-溴-6-氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.027)N-(2-溴苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺、(4.028)N-(4-氯-2,6-二氟苯基)-4-(2-氯-4-氟苯基)-1,3-二甲基-1H-吡唑-5-胺。
5)具有多位点活性的化合物,例如(5.001)波尔多液(bordeaux mixture)、(5.002)敌菌丹(captafol)、(5.003)克菌丹(captan)、(5.004)百菌清(chlorothalonil)、(5.005)氢氧化铜、(5.006)环烷酸铜(copper naphthenate)、(5.007)氧化铜、(5.008)氧氯化铜(copper oxychloride)、(5.009)硫酸铜(2+)(copper(2+)sulfate)、(5.010)二噻农(dithianon)、(5.011)多果定(dodine)、(5.012)灭菌丹(folpet)、(5.013)代森锰锌(mancozeb)、(5.014)代森锰(maneb)、(5.015)代森联(metiram)、(5.016)代森联锌(metiram zinc)、(5.017)喹啉铜(oxine-copper)、(5.018)丙森锌(propineb)、(5.019)硫和硫制剂(包括多硫化钙)、(5.020)福美双(thiram)、(5.021)代森锌(zineb)、(5.022)福美锌(ziram)、(5.023)6-乙基-5,7-二氧代-6,7-二氢-5H-吡咯并[3',4':5,6][1,4]二噻英并[2,3-c][1,2]噻唑-3-甲腈。
6)诱导宿主防御的化合物,例如(6.001)阿拉酸式苯-S-甲基(acibenzolar-S-甲基)、(6.002)三乙膦酸铝(fosetyl-aluminium)、(6.003)乙膦酸钙(fosetyl-calcium)、(6.004)乙膦酸钠(fosetyl-sodium)、(6.005)异噻菌胺(isotianil)、(6.006)亚磷酸及其盐、(6.007)烯丙苯噻唑(probenazole)、(6.008)噻酰菌胺(tiadinil)。
7)氨基酸和/或蛋白质生物合成抑制剂,例如(7.001)嘧菌环胺(cyprodinil)、(7.002)春雷霉素(kasugamycin)、(7.003)春雷霉素盐酸盐水合物(kasugamycin盐酸盐hydrate)、(7.004)土霉素(oxytetracycline)、(7.005)嘧霉胺(pyrimethanil)。
8)ATP生成抑制剂,例如(8.001)硅噻菌胺(silthiofam)。
9)细胞壁合成抑制剂,例如(9.001)苯噻菌胺(benthiavalicarb)、(9.002)烯酰吗啉(dimethomorph)、(9.003)氟吗啉(flumorph)、(9.004)缬霉威(iprovalicarb)、(9.005)双炔酰菌胺(mandipropamid)、(9.006)丁吡吗啉(pyrimorph)、(9.007)缬菌胺(valifenalate)、(9.008)(2E)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮、(9.009)(2Z)-3-(4-叔丁基苯基)-3-(2-氯吡啶-4-基)-1-(吗啉-4-基)丙-2-烯-1-酮。
10)脂质合成或运输抑制剂,或膜合成抑制剂,例如(10.001)fluoxapiprolin、(10.002)纳他霉素(natamycin)、(10.003)氟噻唑吡乙酮(Oxathiapiprolin)、(10.004)霜霉威(propamocarb)、(10.005)霜霉威盐酸盐(propamocarb hydrochloride)、(10.006)霜霉威-乙膦酸盐(propamocarb-fosetylate)、(10.007)甲基立枯磷(tolclofos-methyl)、(10.008)1-(4-{4-[(5R)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(10.009)1-(4-{4-[(5S)-5-(2,6-二氟苯基)-4,5-二氢-1,2-噁唑-3-基]-1,3-噻唑-2-基}哌啶-1-基)-2-[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酮、(10.010)2-[3,5-二(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(10.011)2-[3,5-双(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氯-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(10.012)2-[3,5-双(二氟甲基)-1H-吡唑-1-基]-1-[4-(4-{5-[2-氟-6-(丙-2-炔-1-基氧基)苯基]-4,5-二氢-1,2-噁唑-3-基}-1,3-噻唑-2-基)哌啶-1-基]乙酮、(10.013)甲磺酸2-{(5R)-3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基酯、(10.014)甲磺酸2-{(5S)-3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-3-氯苯基酯、(10.015)甲磺酸2-{3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-4,5-二氢-1,2-噁唑-5-基}-苯基酯、(10.016)甲磺酸3-[2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氢-2,4-苯并二氧杂卓-6-基酯、(10.017)甲磺酸9-氟-3-[2-(1-{[5-甲基-3-(三氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氢-2,4-苯并二氧杂卓-6-基酯、(10.018)甲磺酸3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-1,5-二氢-2,4-苯并二氧杂卓-6-基酯、(10.019)甲磺酸3-[2-(1-{[3,5-双(二氟甲基)-1H-吡唑-1-基]乙酰基}哌啶-4-基)-1,3-噻唑-4-基]-9-氟-1,5-二氢-2,4-苯并二氧杂卓-6-基酯。
11)黑色素生物合成抑制剂,例如(11.001)tolprocarb、(11.002)三环唑(tricyclazole)。
12)核酸合成抑制剂,例如(12.001)苯霜灵(benalaxyl)、(12.002)精苯霜灵(benalaxyl-M)(kiralaxyl)、(12.003)甲霜灵(metalaxyl)、(12.004)高效甲霜灵(metalaxyl-M)(精甲霜灵(mefenoxam)).
13)信号转导抑制剂,例如(13.001)咯菌腈(fludioxonil)、(13.002)异菌脲(iprodione)、(13.003)腐霉利(procymidone)、(13.004)丙氧喹啉(proquinazid)、(13.005)喹氧灵(quinoxyfen)、(13.006)乙烯菌核利(vinclozolin)。
14)能作为解偶联剂的化合物,例如(14.001)氟啶胺(fluazinam)、(14.002)消螨多(meptyldinocap)。
15)其他化合物,例如(15.001)脱落酸(abscisic acid)、(15.002)aminopyrifen、(15.003)苯噻硫氰(benthiazole)、(15.004)bethoxazin、(15.005)卡巴西霉素(capsimycin)、(15.006)香芹酮(carvone)、(15.007)灭螨锰(chinomethionat)、(15.008)硫杂灵(cufraneb)、(15.009)环氟菌胺(cyflufenamid)、(15.010)霜脲氰(cymoxanil)、(15.011)环丙磺酰胺(cyprosulfamide)、(15.012)dipymetitrone、(15.013)flutianil、(15.014)ipflufenoquin、(15.015)异硫氰酸甲酯(methyl isothiocyanate)、(15.016)米多霉素(mildiomycin)、(15.017)福美镍(nickel dimethyldithiocarbamate)、(15.018)酞菌酯(nitrothal-异丙基)、(15.019)oxyfenthiin、(15.020)五氯苯酚及盐、(15.021)picarbutrazox、(15.022)quinofumelin、(15.023)塔格糖(D-tagatose)、(15.024)tebufloquin、(15.025)叶枯酞(tecloftalam)、(15.026)甲磺菌胺(tolnifanide)、(15.027)2-(6-苄基吡啶-2-基)喹唑啉、(15.028)2-[6-(3-氟-4-甲氧基苯基)-5-甲基吡啶-2-基]喹唑啉、(15.029)2-苯基苯酚及其盐、(15.030)4-氨基-5-氟嘧啶-2-醇(互变异构形式:4-氨基-5-氟嘧啶-2(1H)-酮)、(15.031)4-氧代-4-[(2-苯基乙基)氨基]丁酸、(15.032)5-氨基-1,3,4-噻二唑-2-硫醇、(15.033)5-氯-N'-苯基-N'-(丙-2-炔-1-基)噻吩-2-磺酰肼、(15.034)5-氟-2-[(4-氟苄基)氧基]嘧啶-4-胺、(15.035)5-氟-2-[(4-甲基苄基)氧基]嘧啶-4-胺、(15.036)5-氟-4-亚氨基-3-甲基-1-[(4-甲基苯基)磺酰基]-3,4-二氢嘧啶-2(1H)-酮、(15.037){6-[({[(Z)-(1-甲基-1H-四唑-5-基)(苯基)亚甲基]氨基}氧基)甲基]吡啶-2-基}氨基甲酸丁-3-炔-1-基酯、(15.038)(2Z)-3-氨基-2-氰基-3-苯基丙烯酸乙酯、(15.039)吩嗪-1-甲酸、(15.040)3,4,5-三羟基苯甲酸丙酯、(15.041)喹啉-8-醇、(15.042)喹啉-8-醇硫酸酯(2:1)、(15.043)(1-(4,5-二甲基-1H-苯并咪唑-1-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉)、(15.044)1-(5-(氟甲基)-6-甲基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉、(15.045)1-(5,6-二甲基吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉、(15.046)1-(6-(二氟甲基)-5-甲氧基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉、(15.047)1-(6-(二氟甲基)-5-甲基-吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉、(15.048)1-(6,7-二甲基吡唑并[1,5-a]吡啶-3-基)-4,4-二氟-3,3-二甲基-3,4-二氢异喹啉、(15.049)2-{2-氟-6-[(8-氟-2-甲基喹啉-3-基)氧基]苯基}丙-2-醇、(15.050)3-(4,4,5-三氟-3,3-二甲基-3,4-二氢异喹啉-1-基)喹啉、(15.051)3-(4,4-二氟-3,3-二甲基-3,4-二氢异喹啉-1-基)-8-氟喹啉、(15.052)3-(4,4-二氟-5,5-二甲基-4,5-二氢噻吩并[2,3-c]吡啶-7-基)喹啉、(15.053)3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)喹啉、(15.054)5-溴-1-(5,6-二甲基吡啶-3-基)-3,3-二甲基-3,4-二氢异喹啉、(15.055)8-氟-3-(5-氟-3,3,4,4-四甲基-3,4-二氢异喹啉-1-基)-喹啉、(15.056)8-氟-3-(5-氟-3,3-二甲基-3,4-二氢异喹啉-1-基)-喹啉、(15.057)8-氟-N-(4,4,4-三氟-2-甲基-1-苯基丁-2-基)喹啉-3-甲酰胺、(15.058)8-氟-N-[(2S)-4,4,4-三氟-2-甲基-1-苯基丁-2-基]喹啉-3-甲酰胺、(15.059)9-氟-2,2-二甲基-5-(喹啉-3-基)-2,3-二氢-1,4-苯并氧氮杂环庚三烯、(15.060)N-(2,4-二甲基-1-苯基戊-2-基)-8-氟喹啉-3-甲酰胺、(15.061)N-[(2S)-2,4-二甲基-1-苯基戊-2-基]-8-氟喹啉-3-甲酰胺、(15.062)1,1-二乙基-3-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.063)1,3-二甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.064)1-[[3-氟-4-(5-(三氟甲基)-1,2,4-噁二唑-3-基)苯基]甲基]氮杂环庚烷-2-酮、(15.065)1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]哌啶-2-酮、(15.066)1-甲氧基-1-甲基-3-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.067)1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.068)1-甲氧基-3-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.069)2,2-二氟-N-甲基-2-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]乙酰胺、(15.070)3,3-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]哌啶-2-酮、(15.071)3-乙基-1-甲氧基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]脲、(15.072)4,4-二甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡咯烷-2-酮、(15.073)4,4-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、(15.074)4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基二甲基氨基甲酸酯、(15.075)5,5-二甲基-2-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]异噁唑烷-3-酮、(15.076)5-甲基-1-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]吡咯烷-2-酮、(15.077)1-{4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苄基}-1H-吡唑-4-甲酸乙酯、(15.078){4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基}氨基甲酸甲酯、(15.079)N-(1-甲基环丙基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.080)N-(2,4-二氟苯基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.081)N-(2-氟苯基)-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.082)N,2-二甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、(15.083)N,N-二甲基-1-{4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苄基}-1H-1,2,4-三唑-3-胺、(15.084)N-[(E)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.085)N-[(E)-N-甲氧基-C-甲基-碳亚胺酰基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.086)N-[(Z)-甲氧基亚氨基甲基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.087)N-[(Z)-N-甲氧基-C-甲基-碳亚胺酰基]-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.088)N-[[2,3-二氟-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]-3,3,3-三氟-丙酰胺、(15.089)N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、(15.090)N-[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]环丙烷甲酰胺、(15.091)N-{2,3-二氟-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苄基}丁酰胺、(15.092)N-{4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苄基}环丙烷甲酰胺、(15.093)N-{4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基}丙酰胺、(15.094)N-烯丙基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]乙酰胺、(15.095)N-烯丙基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、(15.096)N-乙基-2-甲基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]丙酰胺、(15.097)N-甲氧基-N-[[4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯基]甲基]环丙烷甲酰胺、(15.098)N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺、(15.099)N-甲基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯硫代甲酰胺、(15.100)N-甲基-N-苯基-4-[5-(三氟甲基)-1,2,4-噁二唑-3-基]苯甲酰胺。
作为混合组分的生物农药
式(I)的化合物可与生物农药组合。
生物农药尤其包括细菌、真菌、酵母菌、植物提取物和由微生物形成的产物,包括蛋白质和次级代谢物。
生物农药包括细菌如产芽孢细菌(spore-forming bacteria)、根定殖细菌(root-colonizing bacteria)和作为生物杀昆虫剂、杀真菌剂或杀线虫剂起作用的细菌。
用作或可用作生物农药的这类细菌的实例为:
解淀粉芽孢杆菌(Bacillus amyloliquefaciens),菌株FZB42(DSM231179);或蜡样芽胞杆菌(Bacillus cereus),尤其是蜡样芽孢杆菌菌株CNCM I-1562;或者坚强芽孢杆菌(Bacillus firmus),菌株I-1582(登记号CNCMI-1582);或短小芽胞杆菌(Bacilluspumilus),尤其是菌株GB34(登记号ATCC 700814)和菌株QST2808(登记号NRRL B-30087);或枯草芽孢杆菌(Bacillus subtilis),尤其是菌株GB03(登记号ATCC SD-1397),或枯草芽孢杆菌菌株QST713(登记号NRRL B-21661)或枯草芽孢杆菌菌株OST 30002(登记号NRRL B-50421);苏云金芽孢杆菌(Bacillus thuringiensis),尤其是苏云金芽孢杆菌以色列亚种(B.thuringiensis subspecies israelensis)(血清型H-14)、菌株AM65-52(登记号ATCC1276),或苏云金芽孢杆菌鲇泽亚种(B.thuringiensis subsp.aizawai),尤其是菌株ABTS-1857(SD-1372),或苏云金芽孢杆菌库尔斯塔克亚种(B.thuringiensis subsp.kurstaki)菌株HD-1,或苏云金芽孢杆菌粉虫变种(thuringiensis subsp.tenebrionis)菌株NB 176(SD-5428);侵入巴斯德氏芽菌(Pasteuria penetrans)、巴斯德氏芽菌属(Pasteuriaspp.)(肾形肾状线虫(Rotylenchulus reniformis nematode))-PR3(登记号ATCC SD-5834);细黄链霉菌(Streptomyces microflavus)菌株AQ6121(=QRD 31.013,NRRL B-50550);鲜黄链霉菌(Streptomyces galbus)菌株AQ 6047(登记号NRRL 30232)。
用作或可用作生物农药的真菌和酵母菌的实例为:
巴西安白僵菌(Beauveria bassiana),尤其是菌株ATCC 74040;盾壳霉(Coniothyrium minitans),尤其是菌株CON/M/91-8(登记号DSM-9660);轮枝孢属(Lecanicillium spp.),尤其是菌株HRO LEC 12;蜡蚧轮枝菌(Lecanicillium lecanii),(曾用名Verticillium lecanii),尤其是菌株KV01;金龟子绿僵菌(Metarhiziumanisopliae),尤其是菌株F52(DSM3884/ATCC 90448);梅奇酵母菌(Metschnikowiafructicola),尤其是菌株NRRL Y-30752;玫烟色拟青霉(Paecilomyces fumosoroseus)(现用名:玫烟色棒束孢(Isaria fumosorosea)),尤其是菌株IFPC 200613,或菌株Apopka 97(登记号ATCC 20874);淡紫拟青霉(Paecilomyces lilacinus),尤其是淡紫拟青霉菌株251(AGAL 89/030550);黄色蠕形霉(Talaromyces flavus),尤其是菌株V117b;深绿木霉(Trichoderma atroviride),尤其是菌株SC1(登记号CBS122089);哈茨木霉(Trichodermaharzianum),尤其是哈茨木霉T39(登记号CNCM I-952)。
用作或可用作生物农药的病毒的实例为:
棉褐带卷蛾(Adoxophyes orana)(夏季水果卷叶蛾(summer fruit tortrix))颗粒型病毒(GV)、苹果蠹蛾(Cydia pomonella(codling moth))颗粒型病毒(GV)、棉铃虫(Helicoverpa armigera(cotton bollworm))核型多角体病毒(NPV)、甜菜夜蛾(Spodoptera exigua(beet armyworm))mNPV、草地贪夜蛾(Spodoptera frugiperda(秋夜蛾(fall armyworm)))mNPV、海灰翅夜蛾(Spodoptera littoralis(非洲棉树叶虫(Africancotton leafworm)))NPV。
还包括作为“接种剂”添加到植物或植物部位或植物器官中的细菌和真菌,这些细菌和真菌通过其特定性质促进植物生长和植物健康。可提及的实例为:
土壤杆菌属(Agrobacterium spp.)、茎瘤固氮根瘤菌(Azorhizobiumcaulinodans)、固氮螺菌属(Azospirillum spp.)、固氮菌属(Azotobacterspp.)、短根瘤菌属(Bradyrhizobium spp.)、伯霍尔德杆菌属(Burkholderia spp.),尤其是洋葱伯霍尔德杆菌(Burkholderia cepacia)(曾用名:洋葱假单胞菌(Pseudomonascepacia))、巨孢囊霉属(Gigaspora spp.)或Gigaspora monosporum、球囊霉属(Glomusspp.)、蜡蘑属(Laccaria spp.)、布赫纳乳杆菌(Lactobacillus buchneri)、类球囊霉属(Paraglomus spp.)、豆包菌(Pisolithus tinctorus)、假单胞菌属(Pseudomonas spp.)、根瘤菌属(Rhizobium spp.)尤其是三叶草根瘤菌(Rhizobium trifolii)、须腹菌属(Rhizopogon spp.)、硬皮锈菌属(Scleroderma spp.)、乳牛肝菌属(Suillus spp.)、链霉菌属(Streptomyces spp.)。
用作或可用作生物农药的植物提取物和由微生物形成的产物(包括蛋白质和次级代谢物)的实例为:
大蒜(Allium sativum)、苦艾(Artemisia absinthium)、印楝素(azadirachtin)、Biokeeper WP、Cassia nigricans、苦皮藤(Celastrus angulatus)、Chenopodiumanthelminticum、壳多糖(chitin)、Armour-Zen、鳞毛蕨(Dryopteris filix-mas)、问荆(Equisetum arvense)、Fortune Aza、Fungastop、Heads Up(奎奴亚藜(Chenopodiumquinoa)皂苷提取物)、除虫菊/除虫菊酯类、苏里南苦木(Quassia amara)、栎树属(Quercus)、皂树属(Quillaja)、Regalia、“RequiemTM杀昆虫剂”、鱼藤酮(rotenone)、鱼尼丁/兰尼碱、聚合草(Symphytum officinale)、艾菊(Tanacetum vulgare)、麝香草酚(thymol)、Triact70、TriCon、旱金莲(Tropaeulum majus)、大荨麻(Urtica dioica)、Veratrin、槲寄生(Viscum album)、十字花科(Brassicaceae)提取物,特别是油菜籽粉末或芥末粉,以及从橄榄油中获得的生物杀虫/杀螨活性物质,特别是作为活性成分的具有碳链长度C16-C20的不饱和脂肪酸/羧酸,例如在商品名为的产品中包含的活性成分。
作为混合组分的安全剂
式(I)的化合物可与安全剂组合,所述安全剂为例如解草酮(benoxacor)、喹氧乙酸(cloquintocet(-mexyl))、解草胺腈(cyometrinil)、环丙磺酰胺(cyprosulfamide)、二氯丙烯胺(dichlormid)、解草唑(fenchlorazole(-ethyl))、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草噁唑(furilazole)、双苯噁唑酸(乙酯)(isoxadifen(-ethyl))、吡唑解草酯(mefenpyr(-diethyl))、萘二甲酸酐(naphthalicanhydride)、解草腈(oxabetrinil)、2-甲氧基-N-{4-[(甲基氨基甲酰基)氨基]苯基}磺酰基)苯甲酰胺(CAS129531-12-0)、4-(二氯乙酰基)-1-氧杂-4-氮杂螺[4.5]癸烷(CAS71526-07-3)、2,2,5-三甲基-3-(二氯乙酰基)-1,3-噁唑烷(CAS 52836-31-4)。
植物和植物部位
所有的植物和植物部位均可根据本发明进行处理。在本文中植物应理解为意指所有植物和植物部位,例如想要和不想要的野生植物或作物植物(包括天然存在的作物植物),例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、糖用甜菜、甘蔗、番茄、辣椒、黄瓜、甜瓜、胡萝卜、西瓜、洋葱、莴苣、菠菜、韭葱、豆类、甘蓝(如卷心菜)和其他蔬菜品种,棉花、烟草、油菜,以及水果植物(水果为苹果、梨、柑橘类水果和葡萄)。作物植物可以为可通过常规的育种和优化方法或者通过生物技术方法和基因工程方法或这些方法的组合而获得的植物,包括转基因植物以及包括可受或不受品种产权(varietal propertyright)保护的植物品种。植物应理解为意指所有发育阶段,例如种子、幼苗和早期(未成熟)植物直至成熟植物。植物部位应理解为意指植物的地上和地下的所有部位和器官,如芽、叶、花和根,给出的实例为叶、针叶、茎、枝干、花、子实体、果实和种子,以及块茎、根和根茎。植物部位还包括采收植物或采收植物部位以及无性和有性繁殖的材料,例如幼苗、块茎、根茎、插条和种子。
本发明使用式(I)的化合物对植物和植物部位进行的处理通过常规处理方法直接进行或使所述化合物作用于环境、生境或储存空间来进行,所述常规处理方法为例如浸渍、喷雾、蒸发、雾化(fogging)、撒播(scattering)、涂抹、注入,以及在繁殖材料、尤其是种子的情况下,还通过施用一层或多层包衣来进行。
如上所述,可根据本发明处理所有植物及其部位。在一个优选的实施方案中,处理野生植物品种和植物栽培种,或通过常规生物育种方法(如杂交或原生质体融合)而获得的那些植物及其部位。在另一优选的实施方案中,处理通过基因工程方法—如果合适,与常规方法组合—而获得的转基因植物和植物栽培种(遗传修饰生物体)及其部位。术语“部位”或“植物的部位”或“植物部位”已在上文中作出解释。本发明用于特别优选处理各市售可得的常规栽培种的植物或正在使用的那些植物。植物栽培种应理解为意指具有新特性(“性状”)并且通过常规育种、通过诱变或通过重组DNA技术获得的植物。它们可以是栽培种、变种、生物型或基因型。
转基因植物、种子处理和整合株系(integration event)
根据本发明,式(I)的化合物可以有利地用于处理转基因植物、植物栽培种或植物部分,这些植物、植物栽培种或植物部分已经接受了赋予这些植物、植物栽培种或植物部分有利和/或有用的特性(性状)的遗传物质。因此,考虑将本发明与一种或多种重组性状或转基因株系或其组合进行组合。为了本申请的目的,转基因株系是通过将特定重组DNA分子插入植物基因组染色体中的特定位置(基因座)而产生。插入会产生一个新的称为“株系”的DNA序列,其特征是插入的重组DNA分子和与该插入的DNA相邻/在该插入的DNA两端的两侧的一定数量的基因组DNA。此类性状或转基因株系包括但不限于害虫抗性、水利用效率、产量性能、耐旱性、种子质量、改进的营养质量、杂交种子生产和除草剂耐受性,其中所述性状相对于缺乏此类性状或转基因株系的植物进行测量。这种有利和/或有用的特性(性状)的具体实例为更好的植物生长、活力、胁迫耐受性、直立性、抗倒伏性、养分吸收、植物营养和/或产量,特别是改善的生长、增加的对高温或低温的耐受性、增加对干旱的耐受性或水或土壤盐分水平的耐受性、提高的开花性能、更容易收获、加速成熟、更高的产量、收获产品的更好的质量和/或更高的营养价值、更长的储存期限和/或收获产品更好的加工性以及增加的对动物和微生物害虫(例如昆虫、蜘蛛、线虫、螨虫、蛞蝓和蜗牛)的抗性或耐受性。
在编码赋予对此类动物和微生物害虫(特别是昆虫)的抗性或耐受性状的蛋白质的DNA序列中,可以特别提及编码Bt蛋白的苏云金芽孢杆菌的遗传物质,其广泛地记载于文献并且为本领域技术人员所熟知。还应提及从细菌如Photorhabdus(WO97/17432和WO98/08932)中提取的蛋白质。可特别提及Bt-Cry或VIP蛋白,其包括CrylA、CryIAb、CryIAc、CryIIA、CryIIIA、CryIIIB2、Cry9c、Cry2Ab、Cry3Bb和CryIF蛋白或其毒性片段;以及其他杂合体或它们的组合,特别是Cry1F蛋白或衍生自Cry1F蛋白的杂合体(hybrid)(例如杂合体Cry1A-Cry1F蛋白或其毒性片段);Cry1A类型的蛋白质或其毒性片段,优选Cry1Ac蛋白或衍生自Cry1Ac蛋白的杂合体(例如杂合体Cry1Ab-CryAc蛋白)或CryAb或Bt2蛋白或其毒性片段;Cry2Ae、Cry2Af或Cry2Ag蛋白或其毒性片段;Cry1A.105蛋白或其毒性片段;VIP3Aa19蛋白、VIP3Aa20蛋白,VIP3A蛋白在COT202或COT203棉花株系中产生;VIP3Aa蛋白或其毒性片段,如记载于Estruch et al.(1996),Proc Natl Acad Sci USA.28;93(11):5389-94中;Cry蛋白如记载于WO2001/47952中;获自Xenorhabdus(记载于WO98/50427中)、Serratia(特别是获自S.entomophila)或Photorhabdus属菌株的农药蛋白,例如获自Photorhabdus的Tc蛋白,如记载于WO98/08932中。这也包括任何这些蛋白的所有变体或突变体,它们在一些氨基酸(1至10,优选1至5)上与任何上述序列(特别是它们的毒性片段的序列)不同,或与转运肽如质体转运肽或另一种蛋白质或肽融合。
这些性质的另一个和特别强调的实例是对一种或多种除草剂例如咪唑啉酮(imidazolinone)、磺酰脲(sulfonylurea)、草甘膦(glyphosate)或膦丝菌素(phosphinothricin)的耐受性。在编码赋予转化的植物细胞或植物对某些除草剂耐受性状的蛋白质的DNA序列中,可以特别提及记载于WO2009/152359中的抗除草剂基因(bar gene)或PAT基因或天蓝色链霉菌(Streptomyces coelicolor)基因,其赋予对草铵膦除草剂的耐受性;一种编码适合的EPSPS(5-烯醇丙酮酸莽草酸3-磷酸合酶(5-Enolpyruvylshikimat-3-phosphat-synthase))的基因,它赋予对以EPSPS为靶标的除草剂的耐受性,特别是例如草甘膦及其盐类的除草剂;编码草甘膦n-乙酰转移酶的基因或编码草甘膦氧化还原酶的基因。其他合适的除草剂耐受性状包括至少一种ALS(乙酰乳酸合酶)抑制剂(例如WO2007/024782),突变鼠耳芥(Arabidopsis)ALS/AHAS基因(例如美国专利6,855,533)、编码2,4-D-单加氧酶的基因,其赋予对2,4-D(2,4-二氯苯氧乙酸)的耐受性,以及编码麦草畏单加氧酶的基因,其赋予对麦草畏(3,6-二氯-2-甲氧基苯甲酸)的耐受性。
这些特性的其他和特别强调的实例是例如由系统获得性抗性(SAR)、系统素、植物抗毒素、诱导子以及抗性基因和相应表达的蛋白质和毒素引起的对植物病原真菌、细菌和/或病毒的抗性增加。
可以根据本发明优先处理的转基因植物或植物栽培品种中特别有用的转基因株系包括:株系531/PV-GHBK04(棉花,昆虫防治,记载于WO2002/040677中),株系1143-14A(棉花,昆虫防治,未保藏,记载于WO2006/128569中);株系1143-51B(棉花,昆虫防治,未保藏,记载于WO2006/128570中);株系1445(棉花、除草剂耐受性、未保藏,记载于USA 2002-120964或WO2002/034946中);株系17053(稻,除草剂耐受性,保藏为PTA-9843,记载于WO2010/117737中);株系17314(稻,除草剂耐受性,保藏为PTA-9844,记载于WO2010/117735中);株系281-24-236(棉花,昆虫防治-除草剂耐受性,保藏为PTA-6233,记载于WO2005/103266或USA 2005-216969中);株系3006-210-23(棉花,昆虫防治-除草剂耐受性,保藏为PTA-6233,记载于USA 2007-143876或WO2005/103266中);株系3272(玉米,质量性状,保藏为PTA-9972,记载于WO2006/098952或USA 2006-230473中);株系33391(小麦,除草剂耐受性,保藏为PTA-2347,记载于WO2002/027004中),株系40416(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-11508,记载于WO 11/075593中);株系43A47(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-11509,记载于WO2011/075595中);株系5307(玉米,昆虫防治,保藏为ATCC PTA-9561,记载于WO2010/077816中);株系ASR-368(翦股颖(bentgrass),除草剂耐受性,保藏为ATCC PTA-4816,记载于USA 2006-162007或WO2004/053062中);株系B16(玉米,除草剂耐受性,未保藏,记载于USA 2003-126634);株系BPS-CV127-9(大豆,除草剂耐受性,保藏为NCIMB Nr.41603,记载于WO2010/080829中);株系BLR1(油菜,雄性不育系的恢复,保藏为NCIMB 41193,记载于WO2005/074671中),株系CE43-67B(棉花,昆虫防治,保藏为DSMACC2724,记载于USA 2009-217423或WO2006/128573中);株系CE44-69D(棉花,昆虫防治,未保藏,记载于USA 2010-0024077中);株系CE44-69D(棉花,昆虫防治,未保藏,记载于WO2006/128571中);株系CE46-02A(棉花,昆虫防治,未保藏,记载于WO2006/128572中);株系COT102(棉花,昆虫防治,未保藏,记载于USA 2006-130175或WO2004/039986中);株系COT202(棉花,昆虫防治,未保藏,记载于USA 2007-067868或WO2005/054479中);株系COT203(棉花,昆虫防治,未保藏,记载于WO2005/054480中);株系DAS21606-3/1606(大豆,除草剂耐受性,保藏为PTA-11028,记载于WO2012/033794中),株系DAS40278(玉米,除草剂耐受性,保藏为ATCC PTA-10244,记载于WO2011/022469);株系DAS-44406-6/pDAB8264.44.06.l(大豆,除草剂耐受性,保藏为PTA-11336,记载于WO2012/075426中),株系DAS-14536-7/pDAB8291.45.36.2(大豆,除草剂耐受性,保藏为PTA-11335,记载于WO2012/075429中),株系DAS-59122-7(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA11384,记载于USA 2006-070139中);株系DAS-59132(玉米,昆虫防治-除草剂耐受性,未保藏,记载于WO2009/100188中);株系DAS68416(大豆,除草剂耐受性,保藏为ATCC PTA-10442,记载于WO2011/066384或WO2011/066360中);株系DP-098140-6(玉米,除草剂耐受性,保藏为ATCC PTA-8296,记载于USA 2009-137395或WO 08/112019中);株系DP-305423-1(大豆,质量性状,未保藏,记载于USA 2008-312082或WO2008/054747中);株系DP-32138-1(玉米,杂交系统,保藏为ATCC PTA-9158,记载于USA 2009-0210970或WO2009/103049中);株系DP-356043-5(大豆,除草剂耐受性,保藏为ATCC PTA-8287,记载于USA 2010-0184079或WO2008/002872中);株系EE-I(茄子,昆虫防治,未保藏,记载于WO 07/091277中);株系Fil 17(玉米,除草剂耐受性,保藏为ATCC 209031,记载于USA 2006-059581或WO 98/044140中);株系FG72(大豆,除草剂耐受性,保藏为PTA-11041,记载于WO2011/063413中),株系GA21(玉米,除草剂耐受性,保藏为ATCC 209033,记载于USA 2005-086719或WO 98/044140中);株系GG25(玉米,除草剂耐受性,保藏为ATCC 209032,记载于USA 2005-188434或WO98/044140中);株系GHB119(棉花,昆虫防治-除草剂耐受性,保藏为ATCC PTA-8398,记载于WO2008/151780中);株系GHB614(棉花,除草剂耐受性,保藏为ATCC PTA-6878,记载于USA 2010-050282或WO2007/017186中);株系GJ11(玉米,除草剂耐受性,保藏为ATCC209030,记载于USA 2005-188434或WO98/044140中);株系GM RZ13(甜菜,病毒抗性,保藏为NCIMB-41601,记载于WO2010/076212中);株系H7-1(糖用甜菜,除草剂耐受性,保藏为NCIMB41158或NCIMB 41159,记载于USA 2004-172669或WO 2004/074492中);株系JOPLIN1(小麦,抗病性,未保藏,记载于USA 2008-064032中);株系LL27(大豆,除草剂耐受性,保藏为NCIMB41658,记载于WO2006/108674或USA 2008-320616中);株系LL55(大豆,除草剂耐受性,保藏为NCIMB 41660,记载于WO 2006/108675或USA 2008-196127中);株系LLcotton25(棉花,除草剂耐受性,保藏为ATCC PTA-3343,记载于WO2003/013224或USA 2003-097687中);株系LLRICE06(稻,除草剂耐受性,保藏为ATCC 203353,记载于US 6,468,747或WO2000/026345中);株系LLRice62(稻,除草剂耐受性,保藏为ATCC203352,记载于WO2000/026345中),株系LLRICE601(稻,除草剂耐受性,保藏为ATCC PTA-2600,记载于USA 2008-2289060或WO2000/026356中);株系LY038(玉米,质量性状,保藏为ATCC PTA-5623,记载于USA 2007-028322或WO2005/061720中);株系MIR162(玉米,昆虫防治,保藏为PTA-8166,记载于USA 2009-300784或WO2007/142840中);株系MIR604(玉米,昆虫防治,未保藏,记载于USA 2008-167456或WO2005/103301中);株系MON15985(棉花,昆虫防治,保藏为ATCC PTA-2516,记载于USA 2004-250317或WO2002/100163中);株系MON810(玉米,昆虫防治,未保藏,记载于USA 2002-102582);株系MON863(玉米,昆虫防治,保藏为ATCC PTA-2605,记载于WO2004/011601或USA 2006-095986中);株系MON87427(玉米,授粉对照,以ATCC PTA-7899保藏,记载于WO2011/062904);株系MON87460(玉米,胁迫耐受性,保藏为ATCC PTA-8910,记载于WO2009/111263或USA 2011-0138504);株系MON87701(大豆,昆虫防治,以ATCC PTA-8194保藏,记载于USA 2009-130071或WO2009/064652中);株系MON87705(大豆,质量性状-除草剂耐受性,保藏为ATCC PTA-9241,记载于USA 2010-0080887或WO2010/037016中);株系MON87708(大豆,除草剂耐受性,保藏为ATCC PTA-9670,记载于WO2011/034704);株系MON87712(大豆,产量,保藏为PTA-10296,记载于WO2012/051199中);株系MON87754(大豆,质量性状,保藏为ATCC PTA-9385,记载于WO2010/024976中);株系MON87769(大豆,质量性状,保藏为ATCC PTA-8911,记载于USA 2011-0067141或WO2009/102873);株系MON88017(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-5582,记载于USA 2008-028482或WO2005/059103中);株系MON88913(棉花,除草剂耐受性,保藏为ATCC PTA-4854,记载于WO2004/072235或USA 2006-059590中);株系MON88302(油菜,除草剂耐受性,保藏为PTA-10955,记载于WO2011/153186),株系MON88701(棉花,除草剂耐受性,保藏为PTA-11754,记载于WO2012/134808),株系MON89034(玉米,昆虫防治,作为ATCC PTA-7455保藏,记载于WO 07/140256或USA 2008-260932中);株系MON89788(大豆,除草剂耐受性,保藏为ATCC PTA-6708,记载于USA 2006-282915或WO2006/130436中);株系MS1 1(油菜,授粉控制-除草剂耐受性,保藏为ATCC PTA-850或PTA-2485,记载于WO2001/031042中);株系MS8(油菜,授粉控制-除草剂耐受性,保藏为ATCC PTA-730,记载于WO2001/041558或USA 2003-188347中);株系NK603(玉米,除草剂耐受性,保藏为ATCC PTA-2478,记载于USA 2007-292854中);株系PE-7(稻,昆虫防治,未保藏,记载于WO2008/114282中);株系RF3(油菜,授粉控制-除草剂耐受性,保藏为ATCC PTA-730,记载于WO2001/041558或USA 2003-188347中);株系RT73(油菜,除草剂耐受性,未保藏,记载于WO2002/036831或USA 2008-070260中);株系SYHT0H2/SYN-000H2-5(大豆,除草剂耐受性,保藏为PTA-11226,记载于WO2012/082548中);株系T227-1(糖用甜菜,除草剂耐受性,未保藏,记载于WO2002/44407或USA 2009-265817中);株系T25(玉米,除草剂耐受性,未保藏,记载于USA 2001-029014或WO2001/051654中);株系T304-40(棉花,昆虫防治-除草剂耐受性,保藏为ATCC PTA-8171,记载于USA 2010-077501或WO2008/122406中);株系T342-142(棉花,昆虫防治,未保藏,记载于WO2006/128568中);株系TC1507(玉米,昆虫防治-除草剂耐受性,未保藏,记载于USA 2005-039226或WO2004/099447中);株系VIP1034(玉米,昆虫防治-除草剂耐受性,保藏为ATCC PTA-3925,记载于WO2003/052073中);株系32316(玉米,昆虫防治-除草剂耐受性,保藏为PTA-11507,记载于WO2011/084632中);株系4114(玉米,昆虫防治-除草剂耐受性,保藏为PTA-11506,记载于WO2011/084621中);株系EE-GM3/FG72(大豆,除草剂耐受性,ATCC登记号PTA-11041)任选地与株系EE-GM1/LL27或株系EE-GM2/LL55(WO2011/063413A2)叠加;株系DAS-68416-4(大豆,除草剂耐受性,ATCC登记号PTA-10442,WO2011/066360Al);株系DAS-68416-4(大豆,除草剂耐受性,ATCC登记号PTA-10442,WO2011/066384Al);株系DP-040416-8(玉米,昆虫防治,ATCC登记号PTA-11508,WO2011/075593Al);株系DP-043A47-3(玉米,昆虫防治,ATCC登记号PTA-11509,WO2011/075595Al中);株系DP-004114-3(玉米,昆虫防治,ATCC登记号PTA-11506,WO2011/084621Al);株系DP-032316-8(玉米,昆虫防治,ATCC登记号PTA-11507,WO2011/084632Al);株系MON-88302-9(油菜,除草剂耐受性,ATCC登记号PTA-10955,WO2011/153186Al);株系DAS-21606-3(大豆,除草剂耐受性,ATCC登记号PTA-11028,WO2012/033794A2);株系MON-87712-4(大豆,质量性状,ATCC登记号PTA-10296,WO2012/051199A2);株系DAS-44406-6(大豆,叠加除草剂耐受性,ATCC登记号PTA-11336,WO2012/075426Al);株系DAS-14536-7(大豆,叠加除草剂耐受性,ATCC登记号PTA-11335,WO2012/075429Al);株系SYN-000H2-5(大豆,除草剂耐受性,ATCC登记号PTA-11226,WO2012/082548A2);株系DP-061061-7(油菜,除草剂耐受性,无保藏号,WO2012071039A1);株系DP-073496-4(油菜,除草剂耐受性,无保藏号,US2012131692);株系8264.44.06.1(大豆,叠加除草剂耐受性,登记号PTA-11336,WO2012075426A2);株系8291.45.36.2(大豆,叠加除草剂耐受性,登记号PTA-11335,WO2012075429A2);株系SYHT0H2(大豆,ATCC登记号PTA-11226,WO2012/082548A2);株系MON88701(棉花,ATCC登记号PTA-11754,WO2012/134808Al);株系KK179-2(苜蓿,ATCC登记号PTA-11833,WO2013/003558Al);株系pDAB8264.42.32.1(大豆,叠加除草剂耐受性,ATCC登记号PTA-11993,WO2013/010094Al),株系MZDT09Y(玉米,ATCC登记号PTA-13025,WO2013/012775Al)。
此外,转基因株系列表由美国农业部(USDA)动植物健康检验局(APHIS)提供,可在其万维网网站aphis.usda.gov上找到。对于本申请,该列表截至本申请的申请日的状态是相关的。
在转基因植物中,赋予所讨论的所需性状的基因/株系也可以彼此组合存在。可以提及的转基因植物的例子包括重要的农作物,例如谷物(小麦、稻、黑小麦、大麦、黑麦、燕麦)、玉米、大豆、马铃薯、糖用甜菜、甘蔗、西红柿、豌豆和其他蔬菜种类、棉花、烟草、油菜,以及水果植物(水果是苹果、梨、柑橘类水果和葡萄),特别强调玉米、大豆、小麦、稻、马铃薯、棉花、甘蔗、烟草和油菜。应特别强调的特性是植物对昆虫、蜘蛛、线虫、蛞蝓和蜗牛的抗性增加,以及植物对一种或多种除草剂的抗性增加。
可优选根据本发明处理的此类植物、植物部分或植物种子的市售可得的实例包括市售可得的产品,例如销售或可以如下商品名获得的植物种子: ROUNDUP />VT DOUBLE />VT TRIPLE />BOLLGARD />ROUNDUP READY /> ROUNDUP2XTENDTM、INTACTA RR2/>和/或XTENDFLEXTM。
作物保护——处理类型
使用常规处理方法利用式(I)的化合物对植物和植物部位进行直接处理或通过作用于其环境、生境或储存空间来进行处理,所述常规处理方法为例如浸渍、喷雾、弥雾、灌溉、蒸发、撒粉、雾化、撒播、发泡、涂抹、铺展、注射、浇水(浸透)、滴灌,以及在繁殖材料、尤其是种子的情况下,还作为粉末进行干种子处理、作为溶液进行湿种子处理、作为水溶性粉末进行浆体处理,通过结壳、通过用一层或多层包衣包覆等进行处理。还可以通过超低容量法施用式(I)的化合物或者将施用形式或式(I)的化合物本身注射到土壤中。
优选的对植物的直接处理为叶面施用,即将式(I)的化合物施用到叶面上,在该情况下处理频率和施用率应根据所述害虫的侵染水平来调节。
在内吸性活性化合物的情况下,式(I)的化合物还经由根系统进入植物。于是通过将式(I)的化合物作用于植物的生境来处理该植物。这可以通过下述方式完成:例如,浸透;或者通过混入土壤或营养液中,即植物的生长场所(例如土壤或水培体系)被液体形式的式(I)的化合物浸渍;或通过土壤施用,即将本发明的式(I)的化合物以固体形式(例如以颗粒剂的形式)引入到植物的生长场所;或者通过滴灌施用(通常也称为“化学灌溉”),即在一定时间内,液体施用来自地表或地下滴灌线的本发明的式(I)的化合物,同时在植物附近的确定位置施加不同量的水。在水稻作物的情况下,还可以通过将式(I)的化合物以固体施用形式(例如作为颗粒剂)计量加入淹没的水稻田来完成。
数字技术
本发明的化合物可以与例如嵌入计算机程序中的模型结合使用,所述模型用于特定地点作物管理(site-specific crop management)、卫星农业、精准农业或精准种植业。此类模型使用来自许多来源的数据支持农业站点的特定地点管理,旨在优化盈利能力、可持续性和环境保护,所述来源为例如土壤、天气、作物(例如类型、生长阶段、植物健康)、杂草(例如类型、生长阶段)、疾病、害虫、养分、水、湿度、生物量、卫星数据、产量等。特别地,此类模型尤其有助于优化农艺决策、控制农药施用的精准度和记录所进行的工作。
例如,如果模型模拟出害虫的发生并计算出已达到推荐对作物植物施用本发明的化合物的阈值,则可根据合适的剂量范围对作物植物施用本发明的化合物。
包括农艺模型在内的市售系统有,例如The Climate Corporation的FieldScriptsTM、BASF的XarvioTM、John Deere的AGLogicTM等。
本发明的化合物还可以与智能喷雾设备组合使用,例如用于选择性喷雾或精准喷雾的设备,该设备附接至或集成于农用车辆中,例如拖拉机、机器人、直升机、飞机、无人驾驶载具(UAV),例如无人机等。这类设备通常包括输入传感器(例如照相机)和被构建用于分析输入数据并基于输入数据的分析提供决策的处理单元,用于将本发明的化合物特定和精确施用于农作物(或杂草)。使用这种智能喷雾器通常需要定位系统(例如GPS接收器)(来定位获取的数据并操纵或控制农用车辆)、地理信息系统(GIS)——代表可理解地图上的信息以及适当的农用车辆以执行所需的农业活动(例如喷洒)的信息。
在一个实施例中,可以从照相机拍摄的图片中检测到害虫。在一个实施例中,可以基于这些图片来识别害虫和/或将害虫分类。在这类识别和/或分类中,可以采用图像处理算法。这类图像处理算法可以使用机器学习的算法,例如人工神经网络、决策树和人工智能算法。以这种方式,可以将本文所述的化合物仅施用在需要它们的地方。
种子处理
人们早已知道通过处理植物种子来防治动物害虫,并且这是不断改进的主题。然而,种子处理涉及一系列不能总是以令人满意的方式得以解决的问题。因此,需要开发保护种子和发芽植物的方法,该方法不需要或至少显著地减少了在储存过程中、在播种后或在植物出苗后农药的额外施用。此外还需要优化所使用的活性化合物的量,以便为种子和发芽植物提供最佳的保护以免受动物害虫的侵害,而所使用的活性化合物则不会损害植物本身。特别地,处理种子的方法还应考虑到害虫抗性或害虫耐受性转基因植物的固有的杀昆虫或杀线虫特性,以便用最少量的农药来实现对种子以及发芽植物的最佳保护。
因此,特别地,本发明还涉及一种通过用式(I)的化合物之一处理种子来保护种子和发芽植物免受害虫侵害的方法。本发明的保护种子和发芽植物免受害虫侵害的方法还包括在一个操作中同时或依序使用式(I)的化合物和混合组分处理种子的方法。这还包括在不同的时间使用式(I)的化合物和混合组分处理种子的方法。
本发明还涉及式(I)的化合物用于处理种子以保护种子和所得植物免受动物害虫侵害的用途。
此外,本发明还涉及使用本发明的式(I)的化合物处理以提供保护使其免受动物害虫侵害的种子。本发明还涉及同时使用式(I)的化合物和混合组分处理的种子。本发明还涉及在不同时间使用式(I)的化合物和混合组分处理的种子。在不同时间点使用式(I)的化合物和混合组分处理的种子的情况下,各物质可以以不同的层存在于种子上。在本文,包含式(I)的化合物和混合组分的层可以任选地被中间层分隔。本发明还涉及其中施用了式(I)的化合物和混合组分作为包衣的组分或作为除包衣外的另一层或另几层的种子。
此外,本发明还涉及在用式(I)的化合物处理后进行薄膜包衣过程以防止种子遭受灰尘磨损的种子。
在式(I)的化合物内吸性地起作用时,产生的优点之一在于以下事实:通过处理种子,不仅保护种子本身,还保护由其得到的植物在出苗后免受动物害虫的侵害。以这种方式,可无需在播种时或在其之后不久对作物进行即时处理。
必须考虑另一个优势:通过用式(I)的化合物处理种子,可促进已处理过的种子的发芽和出苗。
同样认为有利的是,式(I)的化合物还可特别地用于转基因种子。
此外,式(I)的化合物可与信号技术组合物或化合物结合使用,从而使得通过共生体(例如根瘤菌、菌根和/或内生细菌或真菌)更好的定殖(colonization)和/或优化固氮作用。
式(I)的化合物适于保护在农业、温室、林业或园艺中使用的任何植物品种的种子。特别地,其采用以下植物种子的形式:谷物(例如小麦、大麦、黑麦、粟和燕麦)、玉米、棉花、大豆、稻、马铃薯、向日葵、咖啡、烟草、加拿大油菜、油菜、甜菜(例如糖用甜菜和饲用甜菜)、花生、蔬菜(例如番茄、黄瓜、菜豆、十字花科蔬菜、洋葱和莴苣)、水果植物、草坪植物和观赏性植物。特别重要的是处理谷物(例如小麦、大麦、黑麦和燕麦)、玉米、大豆、棉花、加拿大油菜、油菜、蔬菜和稻的种子。
如上所述,用式(I)的化合物处理转基因种子也是特别重要的。这采用通常包含至少一种异源基因的植物的种子的形式,所述异源基因控制特别是具有杀昆虫和/或杀线虫特性的多肽的表达。转基因种子中的异源基因可源自微生物如芽孢杆菌属(Bacillus)、根瘤菌属(Rhizobium)、假单孢菌属(Pseudomonas)、沙雷氏菌属(Serratia)、木霉属(Trichoderma)、棍状杆菌属(Clavibacter)、球囊霉属(Glomus)或胶霉属(Gliocladium)。本发明特别适用于处理包含至少一种源自芽孢杆菌属的异源基因的转基因种子。特别优选衍生自苏云金芽孢杆菌(Bacillus thuringiensis)的异源基因。
在本发明的上下文中,将式(I)的化合物施用于种子。优选在这样的状态下处理种子:其足够稳定以使得在处理过程中避免损害。通常,可在采收和播种之间的任意时间点处理种子。通常使用已与植物分离并且已除去穗轴、壳、茎、荚(coat)、毛或果肉的种子。例如,可使用已采收、清洁并干燥至允许贮存的水分含量的种子。或者,还可使用在干燥之后例如用水处理然后再干燥(例如灌注(priming))的种子。在稻种子的情况下,还可以使用例如在水中浸泡至稻胚芽的某一阶段(‘胚乳(pigeon breast)期’)的种子,这刺激了发芽并使出苗更均匀。
在处理种子时,通常必须注意选择施用于种子的式(I)的化合物的量和/或其他添加剂的量,以使不对种子的发芽产生不利的影响,或不损害所得的植物。特别是在某些施用率下可能会表现出植物毒性效应的活性化合物,必须确保这一点。
通常,将式(I)的化合物以合适的制剂施用于种子。用于种子处理的合适的制剂和方法是本领域技术人员已知的。
可将式(I)的化合物转化为常规的拌种制剂,例如溶液剂、乳剂、悬浮剂、粉剂、泡沫剂、浆剂(slurry)或其他种子包衣组合物,以及ULV制剂。
这些制剂用已知方式通过将式(I)的化合物与常规添加剂(例如常规的增量剂以及溶剂或稀释剂、着色剂、润湿剂、分散剂、乳化剂、消泡剂、防腐剂、二次增稠剂、胶粘剂、赤霉素以及水)进行混合而制备。
可存在于可根据本发明使用的拌种制剂中的着色剂为常用于此目的的所有着色剂。可使用微溶于水的颜料或溶于水的染料。实例包括已知的名称为罗丹明B(RhodamineB)、C.I.颜料红112和C.I.溶剂红1的染料。
可存在于可根据本发明使用的拌种制剂中的有用的润湿剂为促进润湿并通常用于配制农用化学活性化合物的所有物质。优选使用萘磺酸烷基酯,如萘磺酸二异丙酯或萘磺酸二异丁酯。
可存在于可根据本发明使用的拌种制剂中的有用的分散剂和/或乳化剂为常用于配制农用化学活性成分的所有非离子、阴离子和阳离子分散剂。优选使用非离子或阴离子分散剂,或者非离子或阴离子分散剂的混合物。合适的非离子分散剂特别地包括环氧乙烷/环氧丙烷嵌段聚合物、烷基酚聚乙二醇醚和三苯乙烯基苯酚聚乙二醇醚,以及其磷酸化或硫酸化衍生物。合适的阴离子分散剂特别为木质素磺酸盐、聚丙烯酸盐和芳基磺酸盐/甲醛缩合物。
可存在于可根据本发明使用的拌种制剂中的消泡剂为常用于配制农用化学活性成分的所有抑制泡沫的物质。优选使用硅酮消泡剂和硬脂酸镁。
可存在于可根据本发明使用的拌种制剂中的防腐剂为所有可在农用化学组合物中用于此目的的物质。实例包括二氯酚和苄醇半缩甲醛。
可存在于可根据本发明使用的拌种制剂中的二次增稠剂为所有可在农用化学组合物中用于此目的的物质。优选为纤维素衍生物、丙烯酸衍生物、黄原胶、改性粘土以及精细分散的二氧化硅。
可存在于可根据本发明使用的拌种制剂中的胶粘剂为可用于拌种产品的所有常规的粘合剂。聚乙烯基吡咯烷酮、聚乙酸乙烯酯、聚乙烯醇和甲基纤维素(tylose)可被认为是优选的。
可存在于可根据本发明使用的拌种制剂中的赤霉素优选为赤霉素A1、A3(=赤霉酸)、A4和A7;特别优选使用赤霉酸。赤霉素是已知的(参见R.Wegler“Chemie derPflanzenschutz-and ”,第2卷,Springer Verlag,1970,第401-412页)。
可根据本发明使用的拌种制剂可以直接地或在预先用水稀释后用于处理各种不同类型的种子。例如,浓缩剂或可通过用水稀释而由其获得的制剂可用于拌种以下植物的种子:谷物(例如小麦、大麦、黑麦、燕麦和黑小麦),以及玉米、稻、油菜、豌豆、豆类、棉花、向日葵、大豆和甜菜,或各种不同的蔬菜。可根据本发明使用的拌种制剂或其稀释使用形式还可用于拌种转基因植物的种子。
对于用可根据本发明使用的拌种制剂或通过加入水而由其制得的使用形式来处理种子,所有常规用于拌种的混合装置都是有用的。具体而言,拌种过程为将种子置于间歇操作或连续操作的混合器中;加入具体所需量的拌种制剂(以其本身或在预先用水稀释后);以及混合所有物质直到制剂均匀地分布在种子上。如果合适,之后进行干燥操作。
可根据本发明使用的拌种制剂的施用率可在较宽的范围内变化。这由制剂中式(I)的化合物的具体含量以及种子决定。式(I)的化合物的施用率通常为0.001至50g/kg种子,优选0.01至15g/kg种子。
动物健康
在动物健康领域,即兽医学领域,式(I)的化合物对于动物寄生虫、特别是体外寄生虫或体内寄生虫具有活性。术语体内寄生虫特别包括蠕虫和原生动物,如球虫目(coccidia)。体外寄生虫通常且优选为节肢动物,尤其是昆虫或螨类。
在兽医学领域中,具有有利的温血动物毒性的式(I)的化合物适用于防治在家畜、育种动物、动物园动物、实验室动物、实验动物和家养动物的动物育种和动物饲养中出现的寄生虫。它们对寄生虫的所有或特定发育阶段均具有活性。
农业家畜包括例如哺乳动物,如绵羊、山羊、马、驴、骆驼、水牛、兔、驯鹿、扁角鹿,尤其是牛和猪;或家禽,如火鸡、鸭、鹅,尤其是鸡;或鱼或甲壳类动物,如在水产养殖中;或可视情况,昆虫如蜜蜂。
家养动物包括例如哺乳动物,如仓鼠、豚鼠、大鼠、小鼠、毛丝鼠、雪貂,或特别是狗、猫、笼养鸟;爬行动物、两栖动物或观赏鱼。
根据一个具体实施方案,将式(I)的化合物施用于哺乳动物。
根据另一具体实施方案,将式(I)的化合物施用于禽类,即笼养鸟或特别是家禽。
通过使用式(I)的化合物来防治动物寄生虫,旨在减少或预防疾病、死亡病例和性能下降(在肉、乳、羊毛、皮、蛋、蜜等情况下),从而使得动物饲养更经济且更简单,并可实现更好的动物健康。
关于动物健康领域,本文使用的术语“防治”(control或controlling)意指式(I)的化合物有效地将被寄生虫感染的动物中的各种寄生虫的发生率降低至无害水平。更具体而言,本文使用的“防治”意指式(I)的化合物有效地杀死各种寄生虫、抑制其生长或抑制其增殖。
示例性的节肢动物包括但不限于:
虱目(Anoplurida),例如血虱属(Haematopinus spp.)、毛虱属(Linognathusspp.)、虱属(Pediculus spp.)、Phtirus属和管虱属(Solenopotes spp.);
食毛目(Mallophagida)和钝角亚目(Amblycerina)和丝角亚目(Ischnocerina),例如牛羽虱属(Bovicola spp.)、畜虱属(Damalina spp.)、猫虱属(Felicola spp.)、Lepikentron属、禽虱属(Menopon spp.)、嚼虱属(Trichodectes spp.)、毛羽虱属(Trimenopon spp.)、巨羽虱属(Trinoton spp.)、Werneckiella属;
双翅目(Diptera)和长角亚目(Nematocerina)和短角亚目(Brachycerina),例如伊蚊属(Aedes spp.)、按蚊属(Anopheles spp.)、黄虻属(Atylotus spp.)、蜂虱蝇属(Braula spp.)、丽蝇属(Calliphora spp.)、金蝇属(Chrysomyia spp.)、斑虻属(Chrysopsspp.)、库蚊属(Culex spp.)、库蠓属(Culicoides spp.)、真蚋属(Eusimulium spp.)、厕蝇属(Fannia spp.)、胃蝇属(Gasterophilus spp.)、舌蝇属(Glossina spp.)、角蝇属(Haematobia spp.)、麻虻属(Haematopota spp.)、虱蝇属(Hippobosca spp.)、瘤虻属(Hybomitra spp.)、齿股蝇属(Hydrotaea spp.)、皮蝇属(Hypoderma spp.)、羊虱蝇属(Lipoptena spp.)、绿蝇属(Lucilia spp.)、罗蛉属(Lutzomyia spp.)、蜱蝇属(Melophagus spp.)、莫蝇属(Morellia spp.)、家蝇属(Musca spp.)、短蚋属(Odagmiaspp.)、狂蝇属(Oestrus spp.)、Philipomyia属、白蛉属(Phlebotomus spp.)、鼻狂蝇属(Rhinoestrus spp.)、麻蝇属(Sarcophaga spp.)、蚋属(Simulium spp.)、螫蝇属(Stomoxys spp.)、虻属(Tabanus spp.)、大蚊属(Tipula spp.)、维蚋属(Wilhelmiaspp.)、污蝇属(Wohlfahrtia spp.);
蚤目(Siphonapterida),例如角叶蚤属(Ceratophyllus spp.)、栉头蚤属(Ctenocephalides spp.)、蚤属(Pulex spp.)、潜蚤属(Tunga spp.)、客蚤属(Xenopsyllaspp.);
异翅目(Heteropterida),例如臭虫属(Cimex spp.)、锥蝽属(Panstrongylusspp.)、红猎蝽属(Rhodnius spp.)、锥猎蝽属(Triatoma spp.);以及来自蜚蠊目(Blattarida)的令人生厌的害虫和卫生害虫。
此外,在节肢动物中,可提及例如但不限于以下蜱螨亚纲(acari):
蜱螨亚纲(Acari)(蜱螨目(Acarina))和后气门目(Metastigmata),例如软蜱科(argasidae)如锐缘蜱属(Argas spp.)、钝缘蜱属(Ornithodorus spp.)、耳蜱属(Otobiusspp.),硬蜱科(Ixodidae)如花蜱属(Amblyomma spp.)、革蜱属(Dermacentor spp.)、血蜱属(Haemophysalis spp.)、璃眼蜱属(Hyalomma spp.)、硬蜱属(Ixodes spp.)、扇头蜱属(Rhipicephalus(牛蜱属(Boophilus))spp.)、扇头蜱属(Rhipicephalus spp.)(多宿主蜱的原始属);中气门目(mesostigmata)如皮刺螨属(Dermanyssus spp.)、禽刺螨属(Ornithonyssus spp.)、肺刺螨属(Pneumonyssus spp.)、刺利螨属(Raillietia spp.)、胸孔螨属(Sternostoma spp.)、厉螨属(Tropilaelaps spp.)、瓦螨属(Varroa spp.);辐螨目(Actinedida)(前气门目(Prostigmata)),例如蜂盾螨属(Acarapis spp.)、姬螯螨属(Cheyletiella spp.)、蠕形螨属(Demodex spp.)、Listrophorus属、肉螨属(Myobiaspp.)、新恙螨属(Neotrombicula spp.)、禽螯螨属(Ornithocheyletia spp.)、疮螨属(Psorergates spp.)、恙螨属(Trombicula spp.);和粉螨目(Acaridida)(无气门目(Astigmata)),例如粉螨属(Acarus spp.)、嗜木螨属(Caloglyphus spp.)、皮螨属(Chorioptes spp.)、气囊螨属(Cytodites spp.)、颈下螨属(Hypodectes spp.)、鸟疥螨属(Knemidocoptes spp.)、鸡雏螨属(Laminosioptes spp.)、耳螨属(Notoedres spp.)、耳疥螨属(Otodectes spp.)、痒螨属(Psoroptes spp.)、翅螨属(Pterolichus spp.)、疥螨属(Sarcoptes spp.)、Trixacarus属、食酪螨属(Tyrophagus spp.)。
示例性的寄生性原生动物包括但不限于:
鞭毛纲(Mastigophora)(鞭毛虫纲(Flagellata)),例如:
后滴门(Metamonada):双滴虫目(Diplomonadida),例如贾第虫属(Giardiaspp.)、螺旋核虫属(Spironucleus spp.)。
Parabasala:毛滴虫目(Trichomonadida),例如组织滴虫属(Histomonas spp.)、五鞭毛滴虫属(Pentatrichomonas spp.)、四毛滴虫属(Tetratrichomonas spp.)、毛滴虫属(Trichomonas spp.)、三毛滴虫属(Tritrichomonas spp.)。
眼虫门(Euglenozoa):锥体虫目(Trypanosomatida),例如利什曼原虫属(Leishmania spp.)、锥体虫属(Trypanosoma spp.)。
肉鞭虫亚门(Sarcomastigophora)(肉足亚门(Rhizopoda)),例如内阿米巴科(Entamoebidae),例如内阿米巴属(Entamoeba spp.)、Centramoebidae,例如棘变形虫属(Acanthamoeba sp.)、Euamoebidae,例如哈氏虫属(Harmanella sp.)。
囊泡虫类(Alveolata),如顶复亚门(Apicomplexa)(孢子重亚门(Sporozoa)):如隐孢子虫属(Cryptosporidium spp.);艾美耳球虫目(Eimeriida),例如贝诺孢子虫属(Besnoitia spp.)、囊等孢虫属(Cystoisospora spp.)、艾美球虫属(Eimeria spp.)、哈蒙德虫属(Hammondia spp.)、等孢子球虫属(Isospora spp.)、新孢子虫属(Neospora spp.)、肉孢子虫属(Sarcocystis spp.)、弓形虫属(Toxoplasma spp.);Adeleida目,例如肝簇虫属(Hepatozoon spp.)、克洛虫属(Klossiella spp.);血孢子虫目(Haemosporida),例如住白虫属(Leucocytozoon spp.)、疟原虫属(Plasmodium spp.);梨形虫目(Piroplasmida),例如巴贝虫属(Babesia spp.)、纤毛虫属(Ciliophora spp.)、Echinozoon属、泰勒虫属(Theileria spp.);Vesibuliferida目,例如肠袋虫属(Balantidium spp.)、布克斯顿纤毛虫属(Buxtonella spp.)。
微孢子门(Microspora),例如脑胞内原虫属(Encephalitozoon spp.)、肠孢虫属(Enterocytozoon spp.)、球形虫属(Globidium spp.)、微粒子虫属(Nosema spp.),以及例如粘原虫属(Myxozoa spp.)。
对人或动物致病的蠕虫包括例如棘头虫纲(acanthocephala)、线虫、舌形动物门(pentastoma)和扁形动物门(platyhelmintha)(如,单殖亚纲(monogenea)、绦虫(cestodes)和吸虫(trematodes))。
示例性的蠕虫包括但不限于:
单殖亚纲:例如:指环虫属(Dactylogyrus spp.)、三代虫属(Gyrodactylusspp.)、Microbothrium属、多盘吸虫属(Polystoma spp.)、Troglecephalus属;
绦虫:假叶目(Pseudophyllidea),例如:吸叶绦虫属(Bothridium spp.)、裂头绦虫属(Diphyllobothrium spp.)、复殖孔绦虫属(Diplogonoporus spp.)、Ichthyobothrium属、舌状绦虫属(Ligula spp.)、Schistocephalus属、迭宫绦虫属(Spirometra spp.);
圆叶目(Cyclophyllidea),例如:Andyra属、裸头绦虫属(Anoplocephala spp.)、无卵黄腺绦虫属(Avitellina spp.)、伯特绦虫属(Bertiella spp.)、鸣绦虫属(Cittotaenia spp.)、代凡绦虫属(Davainea spp.)、双睾绦虫属(Diorchis spp.)、复孔绦虫属(Diplopylidium spp.)、犬复孔绦虫属(Dipylidium spp.)、棘球绦虫属(Echinococcus spp.)、棘叶绦虫属(Echinocotyle spp.)、棘鳞绦虫属(Echinolepisspp.)、泡尾绦虫属(Hydatigera spp.)、膜壳绦虫属(Hymenolepis spp.)、约优克斯绦虫属(Joyeuxiella spp.)、中殖孔绦虫属(Mesocestoides spp.)、蒙尼茨绦虫属(Monieziaspp.)、副裸头绦虫属(Paranoplocehala spp.)、瑞利绦虫属(Raillietina spp.)、西里西亚绦虫属(Stilesia spp.)、带绦虫属(Taenia spp.)、曲子宫绦虫属(Thysaniezia spp.)、Thysanosomsa属;
吸虫:选自复殖纲(Digenea),例如:澳毕吸虫属(Austrobilharzia spp.)、短咽吸虫属(Brachylaima spp.)、杯殖吸虫属(Calicophoron spp.)、下弯吸虫属(Catatropisspp.)、支睾吸虫属(Clonorchis spp.)、肛瘤吸虫属(Collyriclum spp.)、殖盘吸虫属(Cotylophoron spp.)、环腔吸虫属(Cyclocoelum spp.)、双腔吸虫属(Dicrocoeliumspp.)、双穴吸虫属(Diplostomum spp.)、棘隙吸虫属(Echinochasmus spp.)、棘缘吸虫属(Echinoparyphium spp.)、棘口吸虫属(Echinostoma spp.)、阔盘吸虫属(Eurytemaspp.)、片形吸虫属(Fasciola spp.)、片形吸虫属(Fascioloides spp.)、姜片吸虫属(Fasciolopsis spp.)、菲策吸虫(Fischoederius spp.)、腹袋吸虫属(Gastrothylacusspp.)、巨毕吸虫属(Gigantobilharzia spp.)、巨盘吸虫属(Gigantoctyle spp.)、异形吸虫属(Heterophyes spp.)、低颈吸虫属(Hypoderaeum spp.)、彩蚴吸虫属(Leucochloridium spp.)、后殖吸虫属(Metagonimus spp.)、次睾吸虫属(Metorchisspp.)、侏形吸虫属(Nanophyetus spp.)、背孔吸虫属(Notocotylus spp.)、后睾吸虫属(Opisthorchis spp.)、鸟毕吸虫属(Ornithobilharzia spp.)、并殖吸虫属(Paragonimusspp.)、同端盘吸虫属(Paramphistomum spp.)、斜睾吸虫属(Plagiorchis spp.)、茎双穴吸虫属(Posthodiplostomum spp.)、前殖吸虫属(Prosthogonimus spp.)、血吸虫属(Schistosoma spp.)、毛毕吸虫属(Trichobilharzia spp.)、鲑吸虫属(Troglotremaspp.)、盲腔吸虫属(Typhlocoelum spp.);
线虫:毛线目(Trichinellida),例如:毛细线虫属(Capillaria spp.)、Eucoleus属、Paracapillaria属、旋毛虫属(Trichinella spp.)、Trichomosoides属、鞭虫属(Trichuris spp.);
垫刃目(Tylenchida),例如:细丝鲶属(Micronema spp.)、Parastrangyloides属、类圆线虫属(Strongyloides spp.);
杆形目(Rhabditida),例如:猫圆线虫属(Aelurostrongylus spp.)、裂口线虫属(Amidostomum spp.)、钩虫线虫属(Ancylostoma spp.)、血管圆线虫属(Angiostrongylusspp.)、Bronchonema属、仰口线虫属(Bunostomum spp.)、夏伯特线虫属(Chabertia spp.)、古柏线虫属(Cooperia spp.)、Cooperioides属、环体线虫属(Crenosoma spp.)、杯口属(Cyathostomum spp.)、Cyclococercus属、Cyclodontostomum属、杯杯属(Cylicocyclusspp.)、杯冠属(Cylicostephanus spp.)、柱咽属(Cylindropharynx spp.)、囊尾线虫属(Cystocaulus spp.)、网尾线虫属(Dictyocaulus spp.)、鹿圆线虫属(Elaphostrongylusspp.)、类丝虫属(Filaroides spp.)、球首属(Globocephalus spp.)、细纹线虫属(Graphidium spp.)、辐首线虫属(Gyalocephalus spp.)、血矛线虫属(Haemonchus spp.)、螺旋线虫属(Heligmosomoides spp.)、猪圆线虫属(Hyostrongylus spp.)、马歇尔线虫属(Marshallagia spp.)、后圆线虫属(Metastrongylus spp.)、缪勒线虫属(Muelleriusspp.)、板口线虫属(Necator spp.)、细颈线虫属(Nematodirus spp.)、新圆线虫属(Neostrongylus spp.)、日本圆线虫属(Nippostrongylus spp.)、尖柱线虫属(Obeliscoides spp.)、食道齿属(Oesophagodontus spp.)、食道口线虫属(Oesophagostomum spp.)、沃鲁线虫属(Ollulanus spp.)、鸟圆线虫属(Ornithostrongylus spp.)、奥斯勒线虫属(Oslerus spp.)、奥斯特线虫属(Ostertagiaspp.)、副库柏属(Paracooperia spp.)、Paracrenosoma属、副类丝虫属(Parafilaroidesspp.)、拟马鹿圆线虫属(Parelaphostrongylus spp.)、肺尾属(Pneumocaulus spp.)、肺圆线虫属(Pneumostrongylus spp.)、杯口线虫属(Poteriostomum spp.)、原圆线虫属(Protostrongylus spp.)、Spicocaulus属、冠尾线属(Stephanurus spp.)、圆线虫属(Strongylus spp.)、比翼属(Syngamus spp.)、背带线虫属(Teladorsagia spp.)、毛线属(Trichonema spp.)、毛圆线虫属(Trichostrongylus spp.)、三齿属(Triodontophorusspp.)、隐圆线虫属(Troglostrongylus spp.)、弯口属(Uncinaria spp.);
旋尾目(Spirurida),例如:棘唇线虫属(Acanthocheilonema spp.)、异尖线虫属(Anisakis spp.)、禽蛔虫属(Ascaridia spp.)、蛔虫属(Ascaris spp.)、斜环咽线虫属(Ascarops spp.)、无刺线虫属(Aspiculuris spp.)、贝利蛔线虫属(Baylisascarisspp.)、布鲁线虫属(Brugia spp.)、Cercopithifilaria属、Crassicauda属、棘唇线虫属(Dipetalonema spp.)、噁丝虫属(Dirofilaria spp.)、龙线虫属(Dracunculus spp.)、德拉西线虫属(Draschia spp.)、蛲虫属(Enterobius spp.)、丝虫属(Filaria spp.)、颚口线虫属(Gnathostoma spp.)、筒线虫属(Gongylonema spp.)、丽线虫属(Habronema spp.)、异刺线虫属(Heterakis spp.);光丝虫属(Litomosoides spp.)、罗阿丝虫属(Loa spp.)、盘尾丝虫属(Onchocerca spp.)、尖尾线虫属(Oxyuris spp.)、副柔线属(Parabronemaspp.)、副丝虫属(Parafilaria spp.)、副蛔虫属(Parascaris spp.)、栓尾线虫属(Passalurus spp.)、泡翼线虫属(Physaloptera spp.)、普氏线虫属(Probstmayriaspp.)、Pseudofilaria属、腹腔丝虫属(Setaria spp.)、Skjrabinema属、旋毛线虫属(Spirocerca spp.)、冠丝虫属(Stephanofilaria spp.)、Strongyluris属、管状线虫属(Syphacia spp.)、吸吮线虫属(Thelazia spp.)、弓蛔线虫属(Toxascaris spp.)、弓蛔虫属(Toxocara spp.)、吴策线虫属(Wuchereria spp.);
棘头虫纲(Acanthocephala):寡棘吻目(Oligacanthorhynchida),例如:巨吻棘头虫属(Macracanthorhynchus spp.)、前睾棘头虫属(Prosthenorchis spp.);Moniliformida目,例如:念珠棘虫属(Moniliformis spp.);
多形目(Polymorphida),例如细颈棘头虫属(Filicollis spp.);棘吻目(Echinorhynchida),例如棘头花属(Acanthocephalus spp.)、棘吻虫属(Echinorhynchusspp.)、似细吻棘头虫属(Leptorhynchoides spp.);
舌形动物门(Pentastoma):蛇舌状虫目(Porocephalida),例如舌形虫属(Linguatula spp.)。
在兽医学领域和动物饲养中,通过本领域通常已知的方法(例如经肠内、胃肠外、真皮或鼻途径)以合适的制剂形式施用式(I)的化合物。施用可以预防性地、补救性地(metaphylactically)或治疗性地进行。
因此,本发明的一个实施方案涉及用作药剂的式(I)的化合物。
另一个方面涉及用作抗体内寄生虫剂的式(I)的化合物。
另一具体的方面涉及用作抗蠕虫剂、更特别是用作杀线虫剂、杀扁形动物剂、杀棘头虫剂或杀舌形动物剂的式(I)的化合物。
另一具体的方面涉及用作抗原生动物剂的式(I)的化合物。
另一方面涉及用作抗体外寄生虫剂、尤其是杀节肢动物剂、更特别是杀昆虫剂或杀螨剂的式(I)的化合物。
本发明的其他方面为兽用制剂,其包含有效量的至少一种式(I)的化合物和至少一种以下物质:药学上可接受的赋形剂(例如固体或液体稀释剂)、药学上可接受的助剂(例如表面活性剂),尤其是通常用于兽用制剂中的药学上可接受的赋形剂和/或药学上可接受的助剂。
本发明的相关方面为一种制备如本文所述的兽用制剂的方法,其包括以下步骤:将至少一种式(I)的化合物与药学上可接受的赋形剂和/或助剂、尤其是与通常用于兽用制剂中的药学上可接受的赋形剂和/或助剂进行混合。
本发明的另一具体方面为兽用制剂及其制备方法,所述兽用制剂选自杀体外寄生虫制剂和杀体内寄生虫制剂,更特别选自上述方面的驱虫、抗原生动物和杀节肢动物制剂,甚至更特别选自杀线虫、杀扁形动物、杀棘头虫、杀舌形动物、杀昆虫和杀螨制剂。
另一方面涉及一种治疗寄生虫感染、尤其是由选自本文所提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染的方法,所述方法通过在需要治疗的动物、尤其是非人动物中施用有效量的式(I)的化合物来进行。
另一方面涉及一种治疗寄生虫感染、尤其是由选自本文所提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染的方法,所述方法通过向需要治疗的动物、尤其是非人动物施用本文所定义的兽用制剂来进行。
另一方面涉及式(I)的化合物在治疗动物、尤其是非人动物的寄生虫感染、尤其是由选自本文所提及的体外寄生虫和体内寄生虫的寄生虫所引起的感染中的用途。
在本发明的动物健康或兽医领域的上下文中,术语“治疗”包括预防性的、补救性的或治疗性的治疗。
在一个具体实施方案中,提供用于兽医领域的至少一种式(I)的化合物与其他活性成分,尤其是与杀体内寄生虫剂和杀体外寄生虫剂的混合物。
在动物健康领域,“混合物”不仅是指将两种(或更多种)不同的活性成分以联合制剂进行配制并相应地一起施用,而且还指包含每种活性化合物的单独制剂的产品。因此,如果施用多于两种活性化合物时,则可将所有活性化合物以联合制剂进行配制或者可将所有活性化合物以单独制剂进行配制;还可为混合的形式,其中一些活性化合物共同配制而一些活性化合物单独配制。单独的制剂可允许单独或依次施用所述活性化合物。
本文中以其通用名称提及的活性化合物是已知的,并且记载于例如《农药手册》(Pesticide Manual)中(参见上文),或者可以在互联网(例如http://www.alanwood.net/pesticides)上检索到。
作为混合配伍剂的杀体外寄生虫剂的示例性活性成分包括但不限于上文详细列出的杀昆虫剂和杀螨剂。其他可使用的活性成分按照上述基于现行的IRAC作用方式分类方案的分类列于下文中:(1)乙酰胆碱酯酶(AChE)抑制剂;(2)GABA-门控氯化物通道阻断剂;(3)钠通道调节剂;(4)烟碱乙酰胆碱受体(nAChR)竞争调节剂;(5)烟碱乙酰胆碱受体(nAChR)变构调节剂;(6)谷氨酸门控氯化物通道(GluCl)变构调节剂;(7)保幼激素模仿物;(8)各种非特异性(多位点)抑制剂;(9)弦音器官调节剂;(10)螨生长抑制剂;(12)线粒体ATP合成酶抑制剂,如ATP干扰剂;(13)通过阻断质子梯度的氧化磷酸化的解偶联剂;(14)烟碱乙酰胆碱受体通道阻断剂;(15)几丁质生物合成抑制剂,0型;(16)几丁质生物合成抑制剂,1型;(17)蜕皮干扰剂(尤其是对于双翅目(Diptera),即双翅昆虫);(18)蜕皮激素受体激动剂;(19)章鱼胺受体激动剂;(21)线粒体复合物I电子传递抑制剂;(25)线粒体复合物II电子传递抑制剂;(20)线粒体复合物III电子传递抑制剂;(22)电压依赖型钠通道阻断剂;(23)乙酰基CoA羧化酶抑制剂;(28)鱼尼丁受体调节剂;(30)GABA门控氯化物通道变构调节剂。
具有未知或非特异性的作用方式的活性化合物,如fentrifanil、氧嘧酰胺(fenoxacrim)、cycloprene、乙酯杀螨醇(chlorobenzilate)、杀虫脒(chlordimeform)、氟苯灭(flubenzimine)、地昔尼尔(dicyclanil)、磺胺螨酯(amidoflumet)、灭螨猛(quinomethionate)、三苯噻螨吩(triarathene)、clothiazoben、杀螨氯硫(tetrasul)、油酸钾(potassium oleate)、石油(petroleum)、噁虫酮(metoxadiazone)、gossyplure、氟螨嗪(flutenzin)、溴满酯(bromopropylate)、氟铝酸钠(cryolite);
其他种类的化合物:畜虫威(butacarb)、敌蝇威(dimetilan)、除线威(cloethocarb)、磷虫威(phosphocarb)、嘧啶磷(乙基嘧啶磷)(pirimiphos(-ethyl))、对硫磷(乙基对硫磷)(parathion(-ethyl))、虫螨畏(methacrifos)、水杨酸异丙酯(isopropylo-salicylate)、三氯膦酸酯(trichlorfon)、硫丙磷(sulprofos)、丙虫磷(propaphos)、克线丹(sebufos)、哒硫磷(pyridathion)、发硫磷(prothoate)、除线磷(dichlofenthion)、甲基砜内吸磷(demeton-S-methylsulphone)、氯唑磷(isazofos)、苯腈膦(cyanofenphos)、氯亚胺硫磷(dialifos)、三硫磷(carbophenothion)、特嘧硫磷(autathiofos)、aromfenvinfos(-methyl)、谷硫磷(乙基谷硫磷)(azinphos(-ethyl))、毒死蜱(乙基毒死蜱)(chlorpyrifos(-ethyl))、丁苯硫磷(fosmethilan)、碘硫磷(iodofenphos)、蔬果磷(dioxabenzofos)、安果(formothion)、地虫磷(fonofos)、吡氟硫磷(flupyrazofos)、丰索磷(fensulfothion)、乙嘧硫磷(etrimfos);
有机氯,例如毒杀芬(camphechlor)、林丹(lindane)、七氯(heptachlor);
苯基吡唑类,如乙酰虫腈(acetoprole)、pyrafluprole、pyriprole、vaniliprole、维吉霉素(sisapronil);
异噁唑啉类,如afoxolaner、氟雷拉纳(fluralaner)、lotilaner、sarolaner;
吡唑基-芳基酰胺类,例如nicofluprole、tigolaner;
拟除虫菊酯(pyrethroid),如(顺式-、反式-)甲氧苄氟菊酯((cis-,trans-)metofluthrin)、丙氟菊酯(profluthrin)、三氟醚菊酯(flufenprox)、溴氟菊酯(flubrocythrinate)、fubfenprox、芬氟司林(fenfluthrin)、protrifenbute、pyresmethrin、RU15525、环戊烯丙菊酯(terallethrin)、顺式-苄呋菊酯(cis-resmethrin)、heptafluthrin、bioethanomethrin、生物氯菊酯(biopermethrin)、吡氯氰菊酯(fenpyrithrin)、顺式-氯氰菊酯(cis-cypermethrin)、顺式-苄氯菊酯(cis-permethrin)、氰菊酯(clocythrin)、(高效)氯氟氰菊酯(cyhalothrin(lambda-))、二氯炔戊菊酯(chlovaporthrin),或卤代烃化合物(HCH),
新烟碱类,如硝乙脲噻唑(nithiazine)
dicloromezotiaz,三氟苯嘧啶(triflumezopyrim)
大环内酯类,如奈马克丁(nemadectin)、伊维菌素(ivermectin)、拉替待克丁(latidectin)、莫昔克丁(moxidectin)、司拉克丁(selamectin)、依立诺克丁(eprinomectin)、多拉克丁(doramectin)、埃玛菌素(emamectin benzoate);米尔贝肟(milbemycin oxime)
烯虫硫酯(triprene)、保幼醚(epofenonane)、苯虫醚(diofenolan);
生物制剂、激素或信息素,例如天然产物,如苏云金素(thuringiensin)、十二碳二烯醇(codlemone)或印楝(neem)成分
二硝基酚类,例如敌螨普(dinocap)、消螨通(dinobuton)、乐杀螨(binapacryl);
苯甲酰基脲类,例如氟佐隆(fluazuron)、氟幼脲(penfluron),脒衍生物,例如chlormebuform、螨蜱胺(cymiazole)、得米地曲(demiditraz)
蜂巢杀螨剂(bee hive varroa acaricide),例如有机酸,如甲酸、乙二酸。
作为混合配对剂的杀体内寄生虫剂的示例性活性成分包括但不限于活性驱虫化合物和活性抗原生动物化合物。
活性驱虫化合物包括但不限于以下活性杀线虫、杀吸虫(trematicidally)和/或杀绦虫(cestocidally)化合物:
大环内酯类,例如:依立诺克丁(eprinomectin)、阿巴克丁(abamectin)、奈马克丁(nemadectin)、莫昔克丁(moxidectin)、多拉克丁(doramectin)、司拉克丁(selamectin)、雷皮菌素(lepimectin)、拉替待克丁(latidectin)、弥拜菌素(milbemectin)、伊维菌素(ivermectin)、依马菌素(emamectin)、米尔倍霉素(milbemycin);
苯并咪唑类和probenzimidazole,例如:奥苯达唑(oxibendazole)、甲苯咪唑(mebendazole)、三氯苯咪唑(triclabendazole)、托布津(thiophanate)、丁苯咪唑(parbendazole)、奥吩达唑(oxfendazole)、奈托比胺(netobimin)、芬苯达唑(fenbendazole)、非班太(febantel)、噻苯哒唑(thiabendazole)、环苯达唑(cyclobendazole)、坎苯达唑(cambendazole)、阿苯达唑亚砜(albendazole-sulphoxide)、阿苯达唑(albendazole)、氟苯达唑(flubendazole);
缩肽类,优选环状缩肽,尤其是24元环状缩肽,例如:依吗德塞(emodepside)、PF1022A;
四氢嘧啶类,例如:莫仑太尔(morantel)、噻嘧啶(pyrantel)、奥克太尔(oxantel);
咪唑并噻唑类,例如:布他咪唑(butamisole)、左旋咪唑(levamisole)、四咪唑(tetramisole);
氨基苯基脒类,例如:阿米太尔(amidantel)、脱酰化阿米太尔(dAMD)、三苯双脒(tribendimidine);
氨基乙腈类,例如:莫奈太尔(monepantel);
paraherquamide类,例如:paraherquamide、德奎太尔(derquantel);
水杨酰苯胺类,例如:三溴沙仑(tribromsalan)、溴沙尼特(bromoxanide)、溴替尼特(brotianide)、氯碘沙尼(clioxanide)、氯生太尔(closantel)、氯硝柳胺(niclosamide)、羟氯扎胺(oxyclozanide)、雷复尼特(rafoxanide);
取代的酚类,例如:硝碘酚腈(nitroxynil)、硫氯酚(bithionol)、二碘硝酚(disophenol)、六氯芬(hexachlorophen)、联硝氯酚(niclofolan)、meniclopholan;
有机磷酸酯类,例如:三氯磷酸酯(trichlorfon)、naphthalofos、敌敌畏(dichlorvos/DDVP)、克芦磷酯(crufomate)、蝇毒磷(coumaphos)、哈洛克酮(haloxon);
哌嗪酮/喹啉类,例如:吡喹酮(praziquantel)、依西太尔(epsiprantel);
哌嗪类,例如:哌嗪(piperazine)、羟嗪(hydroxyzine);
四环素类,例如:四环素(tetracyclin)、金霉素(chlorotetracycline)、多西环素(doxycyclin)、土霉素(oxytetracyclin)、罗利环素(rolitetracyclin);
各种其他种类,例如:丁萘脒(bunamidine)、尼立达唑(niridazole)、雷琐太尔(resorantel)、omphalotin、奥替普拉(oltipraz)、硝硫氰酯(nitroscanate)、硝碘酚腈(nitroxynile)、奥沙尼喹(oxamniquine)、mirasan、米拉西尔(miracil)、硫坎酮(lucanthone)、羟胺硫蒽酮(hycanthone)、海涛林(hetolin)、依米丁(emetine)、乙胺嗪(diethylcarbamazine)、双氯酚(dichlorophen)、地芬尼太(diamfenetide)、氯硝西泮(clonazepam)、苄酚宁(bephenium)、硝硫氰胺(amoscanate)、氯舒隆(clorsulon)。
活性抗原生动物化合物包括但不限于以下活性化合物:
三嗪类,例如:地克珠利(diclazuril)、帕那珠利(ponazuril)、来曲珠利(letrazuril)、托曲珠利(toltrazuril);
聚醚离子载体类,例如:莫能菌素(monensin)、盐霉素(salinomycin)、马度米星(maduramicin)、甲基盐霉素(narasin);
大环内酯类,例如:米尔倍霉素(milbemycin)、红霉素(erythromycin);
喹诺酮类,例如:恩氟沙星(enrofloxacin)、普拉沙星(pradofloxacin);
奎宁类,例如:氯喹(chloroquine);
嘧啶类,例如:乙胺嘧啶(pyrimethamine);
磺酰胺类,例如:磺胺喹噁啉(sulfaquinoxaline)、甲氧苄氨嘧啶(trimethoprim)、磺胺氯吡嗪(sulfaclozin);
硫胺素类,例如:安普罗铵(amprolium);
林可胺类,例如:克林霉素(clindamycin);
碳酰苯胺类,例如:咪多卡(imidocarb);
硝基呋喃类,例如:硝呋莫司(nifurtimox);
喹唑啉酮生物碱类,例如:卤夫酮(halofuginon);
各种其他种类,例如:奥沙尼喹(oxamniquin)、巴龙霉素(paromomycin);
来自微生物的疫苗或抗原,所述微生物为例如:罗氏巴贝斯虫亚种(Babesiacanis rossi)、柔嫩艾美耳球虫(Eimeria tenella)、早熟艾美尔球虫(Eimeria praecox)、毒害艾美球虫(Eimeria necatrix)、和缓艾美球虫(Eimeria mitis)、巨型艾美耳球虫(Eimeria maxima)、布氏艾美耳球虫(Eimeria brunetti)、堆型艾美耳球虫(Eimeriaacervulina)、韦氏巴贝斯虫亚种(Babesia canis vogeli)、婴儿利什曼虫(Leishmaniainfantum)、犬巴贝斯虫亚种(Babesia canis canis)、胎生网尾线虫(Dictyocaulusviviparus)。
所有命名的混合配对剂——如果它们的官能团能够形成盐的话——可任选地与合适的碱或酸形成盐。
病媒防治
式(I)的化合物还可用于病媒防治。针对本发明的目的,病媒为能够将病原体例如病毒、蠕虫、单细胞生物和细菌从贮主(植物、动物、人等)传播给宿主的节肢动物,尤其是昆虫或蛛形纲动物。病原体可以机械地传播给宿主(例如通过非叮咬蝇(non-stinging fly)传播沙眼),或者可以通过注射传播给宿主(例如通过蚊传播疟原虫)。
病媒及其传播的疾病或病原体的实例为:
1)蚊
-按蚊属(Anopheles):疟疾、丝虫病;
-库蚊属(Culex):日本脑炎、其他病毒性疾病、丝虫病、其他蠕虫传播;
-伊蚊属(Aedes):黄热病、登革热、其他病毒性疾病、丝虫病;
-蚋科(Simuliidae):蠕虫传播,尤其是盘尾丝虫(Onchocerca volvulus);
-毛蠓科(Psychodidae):利什曼病传播;
2)虱:皮肤感染、流行性斑疹伤寒(epidemic typhus);
3)跳蚤:鼠疫、地方性斑疹伤寒、绦虫;
4)蝇:昏睡病(锥虫病(trypanosomiasis));霍乱、其他细菌性疾病;
5)螨:壁虱病、流行性斑疹伤寒、立克次氏体痘、土拉菌病、圣路易斯脑炎(SaintLouis encephalitis)、蜱媒脑炎(tick-borne encephalitis)(TBE)、克里米亚-刚果出血热(Crimean-Congo haemorrhagic fever)、疏螺旋体病(borreliosis);
6)蜱:borellioses,如Borrelia bungdorferi sensu lato.、达氏疏螺旋体(Borrelia duttoni)、蜱媒脑炎、Q热(贝氏柯克斯体(Coxiella burnetii))、巴贝斯虫(babesioses)(犬巴贝斯虫(Babesia canis canis))、埃立克体病。
就本发明而言,病媒的实例为可向植物传播植物病毒的昆虫,例如蚜虫、蝇、叶蝉或蓟马(thrip)。能够传播植物病毒的其他病媒是蜘蛛螨、虱、甲虫和线虫。
就本发明而言,病媒的其他实例为可向动物和/或人类传播病原体的昆虫和蛛形纲动物,例如蚊,尤其是伊蚊属、按蚊属,例如冈比亚按蚊(A.gambiae)、阿拉伯按蚊(A.arabiensis)、不吉按蚊(A.funestus)、大劣按蚊(A.dirus)(疟疾)和库蚊属,毛蠓科,如白蛉属、罗蛉属、虱、跳蚤、蝇、螨和蜱。
如果式(I)的化合物为抗性突破(resistance-breaking)的,则病媒防治也是可能的。
式(I)的化合物适用于预防由病媒传播的疾病和/或病原体。因此,本发明的另一方面为式(I)的化合物在例如农业、园艺、园林以及休闲设备中、以及在材料和贮存产品的保护中用于病媒防治的用途。
工业材料的保护
式(I)的化合物适用于保护工业材料免受昆虫的侵害或破坏,所述昆虫例如来自鞘翅目、膜翅目、等翅目、鳞翅目、啮虫目和衣鱼目(Zygentoma)。
在本发明的上下文中,工业材料应理解为意指无生命的材料,例如,优选塑料、胶粘剂、胶料、纸和卡片、皮革、木材、加工的木制品和涂料组合物。特别优选本发明的用于保护木材的用途。
在另一实施方案中,式(I)的化合物与至少一种其他杀昆虫剂和/或至少一种杀真菌剂一起使用。
在另一实施方案中,式(I)的化合物作为即用型农药存在,即其不需要进一步改变即可施用于所述材料。合适的其他杀虫剂或杀菌剂特别地为上文提及的那些。
出乎意料地,还发现式(I)的化合物可用于保护与盐水或微咸水接触的物体免受沾污,所述物体特别是船体、隔板、网、建筑物、系泊设备和信号系统。同样,式(I)的化合物还可单独地或与其他活性化合物结合用作防污剂。
卫生领域中动物害虫的防治
式(I)的化合物适用于防治卫生领域中的动物害虫。特别地,本发明可以用于室内领域、卫生领域以及储存产品的保护,特别是用于防治密闭空间中遇到的昆虫、蛛形纲动物、蜱和螨,所述密闭空间为例如住所、工厂大厅、办公室、车辆舱室、畜牧业。为了防治动物害虫,将式(I)的化合物单独使用或与其他活性化合物和/或助剂结合使用。它们优选用于室内杀昆虫剂产品中。式(I)的化合物有效地对抗敏感性和抗性物种,以及对抗全部的发育阶段。
这些害虫包括例如下述害虫:蛛形纲,蝎目(Scorpiones)、蜘蛛目(Araneae)和盲蛛目(Opiliones);唇足纲和倍足纲;昆虫纲蜚蠊目、鞘翅目、革翅目、双翅目、异翅亚目、膜翅目、等翅目、鳞翅目、虱目、啮虫目、跳跃亚目(Saltatoria)或直翅目、蚤目和衣鱼目;软甲纲等足目。
它们以以下方式使用:例如,气溶胶、无压喷雾产品如泵式喷雾剂和雾化喷雾剂、自动雾化系统、喷雾剂、泡沫剂、凝胶剂、具有由纤维素或塑料制成的蒸发片剂的蒸发产品、液体蒸发剂、凝胶和薄膜蒸发剂、推进器驱动的蒸发剂、无动力(energy-free)或无源(passive)的蒸发系统、捕蛾纸、捕蛾袋和捕蛾胶,作为颗粒剂或粉剂,用于撒播的诱饵或诱饵站中。
缩略语和符号
AcOH: 乙酸
aq.: 含水的
br.: 宽峰
d: 双重峰
DABCO 1,4-二氮杂双环[2.2.2]辛烷
DCC: N,N’-二环己基碳二亚胺
DCM: 二氯甲烷
DIPEA: N,N-二异丙基乙基胺
DMF: N,N-二甲基甲酰胺
DMSO: 二甲基亚砜
ee: 对映体过量
eq.: 当量
ES: 电喷射离子化
Et3N 三乙基胺
EtOAc: 乙酸乙酯
h(rs) 小时
HATU: 1-[双(二甲基氨基)亚甲基]-1H-1,2,3-三唑并[4,5-b]吡啶鎓-3-氧化物六氟磷酸盐
HOBt: 1-羟基苯并三唑水合物
HPLC: 高效液相色谱法
iPrOH: 异丙醇
J: 偶联常数
LCMS: 液相色谱-质谱法
m/z: 质荷比
M: 摩尔浓度
m: 多重峰
MeCN 乙腈
MeOH: 甲醇
NaH2PO4 磷酸单钠
NaOH 氢氧化钠
Na2SO4 硫酸钠
NH4Cl 氯化铵
NMR: 核磁共振
q: 四重峰
r.t.: 室温
Rt: 保留时间
s: 单峰
sat.: 饱和的
T: 温度
t: 三重峰
丙基膦酸酐
THF: 四氢呋喃
TMSOK 三甲基硅醇钾
wt.: 重量
xantphos: 4,5-双(二苯基膦)-9,9-二甲基氧杂蒽
δ: 化学位移
λ: 波长
方法与中间体的说明
式(I’)的化合物可如以下方案1中所示进行制备,其中R1、R2、R31、R32和R4如前文所定义,并且X1代表OH或Cl,并且Alk代表C1-C4烷基。
方案1
X1=OH:使式(1)的三唑化合物与式(2a)的羧酸(X1=OH)反应以形成式(3)的化合物。例如,将式(1)的三唑、式(2a)的羧酸(X1=OH)、合适的偶联剂(如HATU、或DCC/HOBt)、合适的碱(如三乙胺或DIPEA)在合适的溶剂(如乙酸乙酯或DMF)中的混合物在约0至100℃的温度下进行混合,得到式(3)的化合物,然后可以对其分离,并在必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
X1=Cl:使式(1)的三唑类化合物与式(2b)的羧酸氯化物(X1=Cl)反应以形成式(3)的化合物。例如,将式(1)的三唑、式(2b)的羧酸氯化物(X1=Cl)、合适的碱(如三乙胺或DIPEA)于合适的溶剂(如二氯甲烷或THF)中的混合物在约0至100℃的温度范围内进行混合,得到式(3)的化合物,然后可以对其分离,并在必要和需要时,使用本领域中众所周知的技术(如色谱法)进行纯化。
式(2a)的羧酸(X1=OH)和式(2b)的羧酸氯化物(X1=Cl)可商购获得或可通过本领域技术人员已知的方法合成。式(2a)的某些羧酸(X1=OH)的合成已经记载于WO 2019/197468中。
通过本领域技术人员已知的方法用胺HNR31R32将式(3)的吡嗪基酯转化为式(I')的吡嗪基酰胺。
或者,根据酰胺键形成策略,将式(3)的吡嗪基酯皂化以形成吡嗪基羧酸,随后将其转化为羧酸氯化物(如果需要)。所需的式(I')酰的胺可以通过本申请中描述的方法或本领域技术人员已知的方法合成。
式(I)的硫代酰胺(其中X=S)可以通过如例如WO 2005/009435中所记载的使用劳森试剂(Lawesson’s reagent)在沸腾的甲苯中处理式(I')的化合物来获得。
式(1)的化合物可如以下方案2中所示进行制备,其中R1如前文所定义,R4为氢或C1-C3烷基,并且Alk为C1-C4烷基。
方案2
式(4)的酰胺与式(5)的N,N-二甲基酰胺二甲缩醛反应以形成式(6)的化合物,其随后与式(7)的取代的肼或其合适的盐(例如盐酸盐)在酸性条件下反应以形成式(8)的化合物。例如,式(4)的化合物与式(5)的N,N-二甲基酰胺二甲缩醛在合适的溶剂(例如CH2Cl2)中在回流下反应以提供式(6)的化合物。除去溶剂后,式(6)的化合物与式(7)的取代的肼或其合适的盐(例如盐酸盐)在合适的溶剂(例如1,4二噁烷、乙酸或此类溶剂的混合物)中在约20至80℃的温度下反应。然后可以分离所得的式(8)化合物,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
用酸处理式(8)的氨基甲酸酯以形成式(1)的胺。例如,式(8)的氨基甲酸酯和合适的酸(例如氯化氢或三氟乙酸)在合适的溶剂(例如1,4-二噁烷)中或者在三氟乙酸(没有额外的溶剂)的情况下在约0至80℃的温度下反应。然后可以将所得的式(1)的胺以其酸式盐的形式进行分离,或者在碱处理后以游离胺的形式进行分离,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
必需的式(4)的酰胺和式(7)的肼或其合适的盐(例如盐酸盐)是可商购的或者可以通过本申请中描述的方法或本领域技术人员已知的方法合成。
例如,式(7)的肼可以如下获得:
类似于WO2021/58595A1,可商购的5-氯吡嗪-2-甲酸甲酯可以通过与肼水合物在溶剂如乙醇中在室温或至高达78℃的升高的温度下反应而转化为相应的吡嗪基肼。
或者,式(I')的化合物可如以下方案3中所示进行制备,其中R1、R2、R31和R32如前文所定义且R4为氢或C1-C3烷基,并且Alk为C1-C4烷基。
方案3
式(9)的酰胺与式(5)的N,N-二甲基酰胺二甲缩醛反应以形成式(10)的化合物,其随后与式(7)的取代的肼或其合适的盐(例如盐酸盐)在酸性条件下反应以形成式(3)的化合物。例如,式(9)的化合物和式(5)的N,N-二甲基酰胺二甲缩醛在合适的溶剂例如(CH2Cl2)中在回流下反应以提供式(10)的化合物。除去溶剂后,式(10)的化合物与式(7)的取代的肼或其合适的盐(例如盐酸盐)在合适的溶剂如(1,4-二噁烷、乙酸或这些溶剂的混合物)在约20至100℃的温度下反应。然后可以分离所得的式(3)化合物,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
必需的式(7)的肼或其合适的盐(例如盐酸盐)是可商购获得的或者可以通过本申请中描述的方法或本领域技术人员已知的方法合成。
通过本领域技术人员已知的方法使用胺HNR31R32将式(3)的吡嗪基酯转化为式(I')的吡嗪基酰胺。
或者,根据酰胺键形成策略,将式(3)的吡嗪基酯皂化以形成吡嗪基羧酸,随后将其转化为羧酸氯化物(如果需要)。所需的式(I')的酰胺可以通过本申请中描述的方法或本领域技术人员已知的方法合成。
或者,式(I')的化合物可如以下方案4中所示进行制备,其中R1、R2、R31和R32如前文所定义且R4为氢或C1-C3烷基,并且Alk为C1-C4烷基。
方案4
根据酰胺键形成策略,将式(11)的吡嗪基酯皂化以形成式(12a)的吡嗪基羧酸,随后通过本领域技术人员已知的方法将其转化为式(12b)的羧酸氯化物(如果需要)。
X=OH:式(12a)的吡嗪基化合物与胺反应以形成式(13)的化合物。例如,将式(12a)的吡嗪基羧酸、胺、合适的偶联剂(例如HATU或DCC/HOBt)、合适的碱例如(三乙胺或DIPEA)在合适的溶剂(例如乙酸乙酯或DMF)中的混合物在约0至100℃的温度下混合以提供式(13)的化合物,然后可以将其分离,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
X=Cl:式(12b)的吡嗪基化合物与胺反应以形成式(13)的化合物。例如,将式(12b)的吡嗪基羧酸氯化物、胺、合适的碱(例如三乙胺或DIPEA)在合适的溶剂(例如二氯甲烷或THF)中的混合物在约0至100℃的温度下混合以提供式(13)的化合物,然后可以将其分离,并且必要和需要时,使用本领域中众所周知的技术(例如色谱法)进行纯化。
式(13)的吡嗪基氯化物通过与肼反应而转化为相应的式(14)的吡嗪基肼。例如,类似于WO2021/58595 A1,将式(13)的吡嗪基氯化物与肼水合物的混合物在合适的溶剂如乙醇中在约0至78℃的温度下混合,以提供式(14)的化合物或其合适的盐(例如盐酸盐),然后可以将其分离,并且必要和需要时,使用本领域众所周知的技术(例如重结晶)进行纯化。
如方案3中所述制备的式(10)化合物与式(14)的吡嗪基肼或其合适的盐(例如盐酸盐)在酸性条件下反应,形成式(I')化合物。例如,式(10)的化合物与式(14)的吡嗪基肼或其合适的盐(例如盐酸盐)在合适的溶剂(如1,4-二噁烷、乙酸或这些溶剂的其混合物)中在20至100℃的温度下反应。然后可以分离所得的式(I')化合物,并且必要和需要时,可以使用本领域众所周知的技术(例如色谱法)进行纯化。
所需的式(9)的酰胺可如以下方案5中所示进行制备,其中R1和R2如前文所记载(也参见WO 2017/192385)。
方案5
式(15)的氨基酰胺与式(2a)的羧酸(X1=OH)反应形成式(9)的化合物。例如,式(15)的氨基酰胺、羧酸(2a)(X1=OH)、合适的偶联剂(例如HATU或DCC/HOBt)、合适的碱(例如三乙胺或DIPEA)的混合物在合适的溶剂(如乙酸乙酯或DMF)中,在约0至100℃的温度下混合以提供式(9)的化合物,然后可以将其分离,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
或者,使式(15)的氨基酰胺与式(2b)的羧酸氯化物(X1=Cl)反应以形成式(9)的化合物。例如,式(15)的氨基酰胺、式(2b)的羧酸氯化物(X1=Cl)、合适的碱(例如三乙胺或DIPEA)在合适的溶剂(例如二氯甲烷或THF)中的混合物在约0至100℃的温度下混合以提供式(9)的化合物,然后可以将其分离,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
式(15)的化合物为可商购获得的或者可以通过本领域技术人员已知的方法合成。式(2a)的羧酸(X1=OH)和式(2b)的羧酸氯化物(X1=Cl)可商购获得或可以通过本领域技术人员已知的方法合成。式(2a)(X1=OH)的某些羧酸的合成已记载于WO 2019/197468中。
方案6示出了含烷基三唑和环烷基三唑的胺(1a)的制备,其中R4为C1-C3烷基或C3-C4环烷基。Z为NH2或OC1-C6烷基。
方案6
N-(叔丁氧基羰基)-丙氨酸(16)与烷基脒(17a,Z=NH2)或烷基亚氨酸酯(17b,Z=OC1-C6烷基)反应以形成式(18a)或(18b)的中间体,其随后与式(7)的取代的肼反应以形成式(8a)的烷基三唑。
例如,在(17a,Z=NH2)(比较J.Org.Chem.2011,76,1177-1179)的情况下,N-(叔丁氧基羰基)-丙氨酸(16)和式(17a)的烷基脒在合适的偶联剂(如HATU)、合适的碱(如三乙胺或DIPEA)的存在下,在合适的溶剂如DMF中,在0至50℃的温度下反应,以形成式(18a)的酰基脒中间体。除去溶剂后,式(18a)的中间体与式(7)的取代的肼或其合适的盐(例如盐酸盐)在合适的溶剂(例如乙酸)中在约20至80℃的温度下反应。然后可以分离所得的式(8a)的烷基三唑,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
在Z=OC1-C6烷基的情况下,N-(叔丁氧基羰基)-丙氨酸(16)和式(17b)的烷基亚氨酸酯或其合适的盐在合适的偶联剂(例如HATU)、合适的碱(例如三乙胺或DIPEA)的存在下,在合适的溶剂(例如THF)中在约0至25℃的温度下反应,以形成式(18b)的酰基亚氨酸酯中间体。加入式(7)的取代的肼或其合适的盐(例如盐酸盐)后,式(18b)的中间体在约20至80℃的温度下反应,得到式(8a)的烷基三唑,然后可以将其分离,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
将式(8a)的氨基甲酸酯用酸处理以形成式(1a)的胺或相关盐,如方案2中关于通式(1)的胺所记载的。
所需的烷基脒(17a)和烷基亚氨酸酯(17b)或它们合适的盐和式(7)的肼或其合适的盐(例如盐酸盐)为可商购获得的或者可以通过本申请中描述的方法或本领域已知的方法进行合成(参见例如WO 2011/133447关于环丙烷甲亚氨酸甲酯盐酸盐的合成)。
方案7示出了含三唑的胺(23)的制备,其中R4、R31和R32如前文所述,Alk为C1-C4烷基且Hal为氯、溴或碘。
方案7
式(6a)、(18a)或(18b)的中间体与式(19)的取代的肼或其合适的盐(例如盐酸盐)在合适的溶剂(例如乙酸)中在约20至80℃的温度下反应。然后可以分离所得的式(20)的5-卤素-吡嗪基-2-基-三唑,并且必要和需要时,使用本领域众所周知的技术(例如色谱法)进行纯化。
随后,在合适的C1-C4醇如甲醇或乙醇中,在钯催化剂(例如1,1'-双(二苯基膦)二茂铁]二氯化钯)的存在下,用一氧化碳对式(20)的5-卤素-吡嗪基-2-基-三唑进行加压,同样记载于WO 2012/035039中。所得式(21)的酯可以通过本申请中描述的方法或本领域技术人员已知的方法转化为式(22)的酰胺。
将式(22)的氨基甲酸酯用酸处理以形成式(23)的胺或相关盐,如方案2中关于通式(1)的胺所记载的。
所需的脒(6a)和亚氨酸酯(18a)和(18b)记载于方案2和方案6中,并且式(19)的肼或其合适的盐(例如盐酸盐)可商购获得或可以通过本申请中所描述的方法或通过本领域技术人员已知的方法进行合成。
例如,式(19)的肼可以如以下获得:
商购可得的2,5-二氯吡嗪可以通过与肼水合物在溶剂(如乙醇)中在室温或至高达78℃的升高的温度下反应而转化为相应的2-氯-5-肼基吡嗪(19a),类似于J.Org.Chem.2020,85,13438。
制备实施例
合成实施例I-032
N-环丙基-5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)-N-甲基吡嗪-2-甲酰胺
步骤1:5-氯吡嗪-2-甲酰氯
向4.0g(25.2mmol)5-氯吡嗪-2-甲酸的溶液中加入3.3ml(37.8mmol)草酰氯,并将反应混合物在室温下搅拌过夜。在压力下蒸发溶剂后,化合物(8.36g)粗产物无需进一步纯化即可用于下一步骤。
步骤2:5-氯-N-环丙基-N-甲基吡嗪-2-甲酰胺
向669.1mg(9.40mmol)环丙基甲胺和1.97ml(11.2mmol)DIPEA在15ml干燥二氯甲烷中的溶液中添加2.07g(6.27mmol,53%纯度)5-氯吡嗪-2-碳酰氯于15ml二氯甲烷的溶液,随后额外加入10ml二氯甲烷。将反应混合物在室温下搅拌3天。将混合物用NaHCO3萃取,经MgSO4干燥并真空蒸发溶剂。粗产物(1.3g,53%纯度)无需进一步纯化即可用于下一步骤。
ESI质量[m/z]:212.1[M+H]+
步骤3:N-环丙基-5-肼基-N-甲基吡嗪-2-甲酰胺
向1.3g(6.14mmol)5-氯-N-环丙基-N-甲基吡嗪-2-甲酰胺于13ml无水THF中的溶液中加入0.60ml(12.2mmol)肼水合物,并将反应混合物在室温下搅拌过夜然后加热回流4小时。将混合物冷却至室温并真空蒸发溶剂。获得的粗产物(1.6g)无需进一步纯化即可用于下一步骤。
ESI质量[m/z]:208.2[M+H]+
步骤4:N-环丙基-5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)-N-甲基吡嗪-2-甲酰胺
向120.0mg(0.37mmol)N-[(2S)-1-氨基-1-氧代丙-2-基]-3-环丙基-5-(三氟甲氧基)苯甲酰胺(类似于WO 2021/099303中所述的方法合成)于3ml二噁烷中的溶液中加入76.0mg(0.56mmol)1,1-二甲氧基-N,N-二甲基乙胺,并将反应混合物加热回流90分钟。一旦混合物冷却至室温,将3ml乙酸和随后96.0mg(0.46mmol)N-环丙基-5-肼基-N-甲基吡嗪-2-甲酰胺加入到混合物中,然后将反应物在100℃下搅拌6小时并在室温下搅拌16小时。将混合物用水稀释并用乙酸乙酯萃取几次。将合并的有机相用饱和NaHCO3溶液、盐水洗涤,干燥,最后在压力下减少溶剂。将残余物通过反相色谱法(H2O/乙腈)纯化,得到44mg(纯度:96%,产率:21%)标题化合物。
ESI质量[m/z]:530.5[M+H]+
1H-NMR(600.4MHz,d6-DMSO):δ=9.166(d,1H),9.095(s,1H),8.772(d,1H),7.507(s,2H),7.268(s,1H),5.982(quin,1H),3.038(s,3H),2.891(m,1H),2.372(s,3H),2.033(m,1H),1.623(d,3H),1.015(m,2H),0.770(m,2H),0.401(m,4H)。
合成实施例I-047
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)-N,N-二甲基吡嗪-2-甲酰胺
步骤1:5-肼基吡嗪-2-甲酸甲酯
在0℃下,向2.0g(11.5mmol)5-氯吡嗪-2-甲酸甲酯于14ml无水THF中的溶液中加入0.43ml肼水合物,并将混合物在0℃下搅拌5小时。然后在0℃下再加入0.42ml(11.5mmol)肼水合物之后,将混合物在室温下搅拌3天。过滤沉淀物,用水洗涤并真空干燥。获得的固体(1.67g,纯度86%)无需进一步纯化即可用于下一步骤。
ESI质量[m/z]:169.1[M+H]+
步骤2:5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯
向800.0mg(2.52mmol)N-[(2S)-1-氨基-1-氧代丙-2-基]-3-环丙基-5-(三氟甲氧基)苯甲酰胺(类似于WO2021/099303中记载的方法合成)于15ml二噁烷的溶液中加入0.50g(3.79mmol)1,1-二甲氧基-N,N-二甲基乙胺,并将反应混合物加热回流90分钟。一旦混合物冷却至室温,将14.6ml乙酸和随后657.0mg(3.08mmol,80%纯度)5-肼基吡嗪-2-甲酸甲酯加入,并将反应混合物在100℃搅拌2.5小时并在室温下搅拌16小时。将混合物用水稀释并用乙酸乙酯萃取几次。将合并的有机相用饱和NaHCO3溶液、盐水洗涤,干燥,最后在压力下减少溶剂。将残余物通过反相色谱法(H2O/乙腈)纯化,得到302mg(纯度:96%,产率:23%)的标题化合物。
ESI质量[m/z]:491.1[M+H]+
1H-NMR(400.2MHz,d6-DMSO),峰列表:δ=9.2399(3.8);9.2366(4.2);9.1797(1.4);9.1619(1.4);9.1069(4.1);9.1035(4.1);7.4875(4.1);7.4842(4.2);7.2734(2.0);6.0218(1.0);6.0043(1.6);5.9868(1.0);3.9407(16.0);3.6489(0.4);3.3583(0.4);3.3368(140.2);3.3177(0.4);2.6767(0.4);2.6722(0.6);2.6679(0.4);2.5257(1.4);2.5210(2.1);2.5122(31.2);2.5078(67.9);2.5032(92.8);2.4987(67.2);2.4943(31.8);2.3818(15.5);2.3346(0.4);2.3300(0.6);2.3255(0.5);2.0478(0.6);2.0392(0.6);2.0269(1.2);2.0144(0.7);2.0060(0.6);1.6259(5.5);1.6085(5.5);1.0420(0.7);1.0308(2.0);1.0252(2.2);1.0147(1.1);1.0099(2.1);1.0043(2.1);0.9940(0.8);0.7864(0.9);0.7756(2.3);0.7705(2.4);0.7634(2.1);0.7582(2.5);0.7467(0.7);-0.0002(0.5)。
步骤3:5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸
向310.0mg(0.61mmol)5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯于9.9ml THF和0.99ml水中的溶液中加入52.0mg(1.22mmol)氢氧化锂,并将混合物在室温下搅拌48小时。将混合物在真空下蒸发并将残余物用10%HCl水溶液酸化。并用乙酸乙酯萃取数次。将合并的有机层用盐水洗涤,经Na2SO4干燥,最后真空蒸发溶剂,得到标题化合物(314.1mg,78%,纯度72%),其不经进一步纯化即用于下一步骤。
ESI质量[m/z]:477.2[M+H]+
1H-NMR(400.2MHz,d6-DMSO),峰列表:δ=9.2202(4.3);9.2169(4.5);9.1830(1.6);9.1654(1.6);9.0843(4.5);9.0810(4.4);7.6068(0.7);7.6032(0.7);7.4873(5.1);7.4836(5.1);7.2997(0.4);7.2724(2.2);6.0209(1.1);6.0035(1.7);5.9860(1.1);4.0556(0.6);4.0378(1.8);4.0200(1.8);4.0022(0.6);3.9928(1.1);3.4076(3.7);2.6772(0.4);2.6726(0.6);2.6681(0.4);2.5261(1.3);2.5213(2.0);2.5126(30.1);2.5082(64.5);2.5037(87.1);2.4992(62.6);2.4948(29.6);2.3797(16.0);2.3300(1.8);2.0602(0.4);2.0482(0.8);2.0394(0.8);2.0272(1.3);2.0150(0.8);2.0065(0.7);1.9900(8.2);1.9100(11.6);1.6278(5.9);1.6104(5.9);1.5229(0.9);1.5053(0.9);1.3553(0.6);1.2336(1.0);1.1930(2.2);1.1818(0.4);1.1752(4.6);1.1694(1.1);1.1574(2.2);1.0553(0.3);1.0481(0.6);1.0412(1.2);1.0297(2.5);1.0244(2.6);1.0137(1.3);1.0090(2.3);1.0034(2.3);0.9930(0.9);0.8147(0.5);0.8121(0.5);0.8020(0.5);0.7971(0.5);0.7890(1.1);0.7784(2.7);0.7733(2.8);0.7663(2.4);0.7610(2.8);0.7494(0.8)。
步骤4:5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)-N,N-二甲基吡嗪-2-甲酰胺
向78mg(0.16mmol)5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸于2ml二氯甲烷中的溶液中加入0.04ml(0.22mmol)N,N-二异丙基乙胺和75.0mg(0.19mmol)HATU,并将反应混合物在室温下搅拌10分钟。最后将0.12ml(0.24mmol)的2M二乙胺于THF中的溶液加入到混合物中并在室温下进一步搅拌过夜。将混合物用5% NaH2PO4水溶液洗涤,用硫酸钠干燥并减压减少溶剂。将残余物通过反相色谱法(H2O/乙腈)纯化,得到47mg(纯度:95%;收率:54%)标题化合物。
ESI质量[m/z]:504.3[M+H]+
1H-NMR(400.2MHz,d6-DMSO),峰列表:δ=9.1715(1.5);9.1537(1.5);9.0847(3.5);9.0813(3.8);8.7661(3.6);8.7628(3.7);7.4930(4.3);7.4897(4.9);7.2721(2.1);7.1192(0.4);7.1159(0.3);5.9764(1.0);5.9589(1.6);5.9413(1.0);3.3324(60.1);3.0436(13.2);2.9689(0.5);2.9478(16.0);2.8682(0.6);2.6763(0.4);2.6717(0.5);2.6672(0.4);2.5252(1.2);2.5204(1.8);2.5115(26.7);2.5073(56.7);2.5029(76.9);2.4984(56.8);2.4942(28.1);2.3694(14.2);2.3339(0.4);2.3295(0.5);2.3252(0.4);2.0602(0.3);2.0476(0.6);2.0391(0.8);2.0268(1.2);2.0144(0.7);2.0060(0.7);1.6254(5.4);1.6080(5.4);1.2336(0.4);1.0420(0.7);1.0308(2.0);1.0253(2.3);1.0149(1.1);1.0101(2.1);1.0045(2.2);0.9942(0.8);0.7901(0.8);0.7793(2.3);0.7743(2.5);0.7674(2.3);0.7621(2.7);0.7506(0.7)。
合成实施例I-097
N-(氰甲基)-5-[3-甲基-5-[(1S)-1-[[3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酰基]-氨基]乙基]-1,2,4-三唑-1-基]吡嗪-2-甲酰胺
步骤1:3-羟基-5-甲磺酰基-苯甲酸甲酯
将3-羟基-5-溴-苯甲酸甲酯(9.5g,41.1mmol)于DMSO(70mL)中的混合物在15℃下在氮气下搅拌10分钟。然后在15℃下在氮气下将甲基亚磺酰氧基钠(6.30g,61.6mmol)、NaOH(986mg,24.6mmol)、CuI(4.70g,24.6mmol)和L-脯氨酸(5.68g,49.3mmol)分批添加至反应混合物中。将混合物加热至100℃并搅拌24小时。通过在15℃下添加H2O(250mL)来淬灭反应混合物,用乙酸乙酯(500mL×3)萃取,经Na2SO4干燥,过滤并减压浓缩,得到残余物。将残余物通过硅胶色谱法纯化(二氯甲烷/甲醇=100/1,0/1)。获得呈黄色固体状的3-羟基-5-甲磺酰基-苯甲酸甲酯(7g,27.6mmol,67.2%产率,91%纯度)。
ESI质量[m/z]:459.1[M+H]+
步骤2:3-(2-溴-1,1,2,2-四氟-乙氧基)-5-甲磺酰基-苯甲酸甲酯
将3-羟基-5-甲基磺酰基-苯甲酸甲酯(7g,30.4mmol)、1,2-二溴-1,1,2,2-四氟乙烷(15.8g,60.8mmol)、Cs2CO3(14.8g,45.6mmol)于DMSO(70mL)的混合物脱气并用氮气吹扫3次,然后将混合物在氮气气氛下在60℃下搅拌12小时。将反应混合物倒入水(100mL)中并搅拌10分钟。用乙酸乙酯(150mL×3)萃取水相。将合并的有机相用盐水(100mL)洗涤,用无水Na2SO4干燥,过滤并真空浓缩。将残余物通过硅胶色谱法(石油醚/乙酸乙酯=100/1,0/1)纯化。获得黄色固体状的3-(2-溴-1,1,2,2-四氟-乙氧基)-5-甲基磺酰基-苯甲酸甲酯(7.1g,15.9mmol,52.5%产率,92%纯度)。
1H NMR(400MHz,DMSO-d6):δ=8.44(t,J=1.5Hz,1H),8.17(s,1H),8.10(d,J=0.8Hz,1H),3.95(s,3H),3.41(s,3H)。
步骤3:3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸甲酯
在50℃和氮气下,向3-(2-溴-1,1,2,2-四氟-乙氧基)-5-甲基磺酰基-苯甲酸甲酯(6.1g,14.9mmol)于AcOH(30mL)的混合物中分批加入Zn(2.92g,44.7mmol)。将混合物在50℃下搅拌12小时。将反应混合物过滤并在真空下浓缩。将残余物通过硅胶(石油醚/乙酸乙酯=100/1,0/1)纯化。获得黄色固体状的3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸甲酯(3.5g,10.1mmol,67.5%产率,95%纯度)。
1H NMR(400MHz,DMSO-d6):δ=8.40(s,1H),8.10(br d,J=15.4Hz,2H),7.05-6.77(m,1H),3.94(s,3H),3.39(s,3H)。
步骤4:3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸
将3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸甲酯(3.5g,10.6mmol)和LiOH*H2O(2M,10.6mL)于THF(25mL)中的混合物脱气并用氮气吹扫3次,然后将混合物在氮气气氛下在15℃下搅拌2小时。将反应混合物减压浓缩,得到残余物,用水(20mL)稀释,用2M KHSO4调节至pH=2,过滤并减压浓缩,得到为白色固体的3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸(3.13g,9.80mmol,92.5%产率,99%纯度)。
1H NMR(400MHz,DMSO-d6):δ=14.35-13.58(m,1H),8.39(s,1H),8.06(br d,J=4.6Hz,2H),7.12-6.70(m,1H),3.38(s,3H)。
ESI质量[m/z]:315.0[M+H]+
步骤5:5-氯吡嗪-2-甲酰氯
向3.0g(18.9mmol)5-氯吡嗪-2-甲酸于20mL二氯甲烷中的溶液中加入2滴N,N-二甲基甲酰胺和2.43ml(28.4mmol)草酰氯,并将反应混合物在室温下搅拌过夜。减压蒸发溶剂后,将粗化合物(3.70g,15.7mmol,82.9%收率,75%纯度)用于下一步骤而无需进一步纯化。
步骤6:5-氯-N-(氰甲基)吡嗪-2-甲酰胺
向2.90g(31.4mmol)氨基乙腈盐酸盐和6.55ml(37.6mmol)DIPEA的30mL无水二氯甲烷的溶液中加入3.70g(20.9mmol)5-氯吡嗪-2-甲酰氯的20ml二氯甲烷的溶液。将反应混合物在室温下搅拌过夜。然后,添加20mL 5%NaH2PO4-溶液,分离各相并用二氯甲烷(2x10mL)萃取水相。将合并的有机层用饱和NaHCO3溶液和盐水洗涤,经Na2SO4干燥并真空蒸发溶剂。粗产物(3.43g,16.8mmol,产率80.5%,纯度96.5%)用于下一步骤而无需进一步纯化。
ESI质量[m/z]:197.1[M+H]+
步骤7:5-肼基-N-(氰甲基)吡嗪-2-甲酰胺
向3.65g(18.6mmol)5-氯-N-(氰基甲基)吡嗪-2-甲酰胺的36.5mL乙醇的溶液中加1.81mL(37.1mmol)肼水合物并将混合物在60℃下搅拌3小时。将反应混合物冷却至0℃并过滤沉淀物。将固体悬浮在30mL热水中,冷却至0℃(冰浴)并再次过滤。然后将固体真空干燥。将获得的产物(3.27g,17.0mmol,91.6%产率)用于下一步骤而无需进一步纯化。
ESI质量[m/z]:193.0[M+H]+
步骤8:N-[(1S)-1-[2-[5-(氰基甲基氨基甲酰基)吡嗪-2-基]-5-甲基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯
向500.0mg(2.66mmol)N-[(1S)-2-氨基-1-甲基-2-氧代-乙基]氨基甲酸叔丁酯的5mL 1,4-二噁烷的溶液中加入0.43mL(2.92mmol)的1,1-二甲氧基-N,N-二甲基乙胺,并将反应混合物加热至50℃并保持1小时。然后减压除去溶剂,加入5mL乙酸,随后加入612mg(3.19mmol)5-肼基-N-(氰基甲基)吡嗪-2-甲酰胺,并将混合物在50℃下搅拌1小时。然后在80℃下保持3小时。冷却至室温后,将反应混合物用水洗涤并用EtOAc(3x)萃取。将合并的有机层用水(2x)洗涤,通过添加Na2SO4干燥,过滤并蒸发。通过反相色谱法(H2O/乙腈)纯化残余物以提供671mg(1.65mmol,62.2%产率,95.2%纯度)的标题化合物。
ESI质量[m/z]:387.5[M+H]+
步骤9:5-[5-[(1S)-1-氨基乙基]-3-甲基-1,2,4-三唑-1-基]-N-(氰基甲基)吡嗪-2-甲酰胺盐酸盐
向672mg(1.74mmol)N-[(1S)-1-[2-[5-(氰基甲基氨基甲酰基)吡嗪-2-基]-5-甲基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯的5.9mL 1,4-二噁烷的溶液中加入8.70mL(34.8mmol)的4M HCl溶液(于1,4-二噁烷中),并将反应混合物在室温下搅拌2小时。然后减压除去溶剂并将残余物悬浮于6mL叔丁基甲醚中。通过过滤收集固体并在减压下干燥。将获得的产物(502mg,1.10mmol,产率63.0%,纯度70.5%)用于下一步骤而无需进一步纯化。
ESI质量[m/z]:287.0[M-Cl]+
步骤10:N-(氰甲基)-5-[3-甲基-5-[(1S)-1-[[3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酰基]氨基]乙基]-1,2,4-三唑-1-基]吡嗪-2-甲酰胺
向68mg(0.22mmol)3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸的2mL二氯甲烷的溶液中加入0.05mL(0.30mmol)N,N-二异丙基乙胺和98.4mg(0.26mmol)HATU并将反应混合物在室温下搅拌30分钟。然后,加入69.6mg 5-[5-[(1S)-1-氨基乙基]-3-甲基-1,2,4-三唑-1-基]-N-(氰基甲基)吡嗪-2-甲酰胺盐酸盐和0.075mL(0.43mmol)N,N-二异丙基乙胺,并将反应混合物在室温下搅拌2小时。减压除去溶剂,将残余物悬浮在8mL乙腈中并通过注射器过滤器过滤。通过反相色谱法(H2O/乙腈)纯化滤液,得到41mg(0.065mmol,29.9%产率,92%纯度)的标题化合物。
ESI质量[m/z]:585.4[M+H]+
1H-NMR(400.2MHz,CD3CN),峰列表:δ=9.1543(10.4);8.4368(0.4);8.4206(0.8);8.2466(1.5);8.2432(2.7);8.2396(1.6);7.9927(0.7);7.9756(0.6);7.9396(1.8);7.9044(1.7);6.4257(0.6);6.3023(0.6);6.2948(1.2);6.2872(0.6);6.1713(0.4);6.1641(0.7);6.1563(0.4);6.1489(1.0);6.1312(1.4);6.1134(0.9);4.3347(4.8);4.3195(4.7);3.9868(0.4);3.7050(0.7);3.1429(0.8);3.1384(1.4);3.1270(16.0);2.3909(15.5);2.3339(0.4);2.2041(116.3);2.1207(0.9);2.1145(0.9);2.1084(0.9);2.1022(0.8);2.0957(0.6);2.0877(0.5);2.0527(0.3);1.9652(1.4);1.9589(1.4);1.9532(17.9);1.9471(34.3);1.9409(49.1);1.9347(33.6);1.9285(17.2);1.7694(0.3);1.6788(6.2);1.6614(6.2);1.4892(0.4);1.4709(0.3);1.2705(0.6);-0.0002(0.4)。
合成实施例I-094
5-[5-[(1S)-1-[[2,6-双(二氟甲基)吡啶-4-羰基]氨基]乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺
步骤1:2,6-双(二氟甲基)吡啶-4-甲酰胺
向500mg(4.09mmol)异烟酰胺和2.42g(8.19mmol)二氟甲烷亚磺酸锌(DFMS)在16mL二氯甲烷和6mL水的混合物中加入315μL(4.09mmol)三氟乙酸。将混合物剧烈搅拌并在室温水浴中冷却,同时非常缓慢地加入1.7mL(12.3mmol,70%水溶液)叔丁基过氧化氢。添加完成后,将混合物在室温下搅拌2小时。添加另外2.42g(8.19mmol)DFMS,随后缓慢添加1.7mL(12.3mmol,70%水溶液)叔丁基过氧化氢。将混合物在室温下搅拌16小时。加入饱和NaHCO3溶液,分离各相并用二氯甲烷(3x)萃取水相。通过添加Na2SO4干燥合并的有机层,过滤并蒸发。通过反相色谱法(H2O/乙腈)纯化粗产物,得到168mg(0.756mmol,18.4%产率,100%纯度)的标题化合物。
ESI质量[m/z]:223.1[M+H]+
步骤2:2,6-双(二氟甲基)吡啶-4-甲酸
向170mg(0.765mmol)2,6-双(二氟甲基)吡啶-4-甲酰胺的1.8mL甲醇的溶液中加入1.32mL(7.63mmol,5.8M水溶液)NaOH,并将反应混合物在65℃搅拌16小时。将混合物减压浓缩,将残余物稀释在水中并用1M HCl酸化。用乙酸乙酯萃取混合物,通过添加Na2SO4干燥有机层,过滤并蒸发,得到178mg(0.688mmol,89.9%产率,86.3%纯度)的标题化合物。
ESI质量[m/z]:224.1[M+H]+
步骤3:(5-氯吡嗪-2-基)肼
在10℃下,向50.0g 2,5-二氯吡嗪(335mmol)的500mL乙醇的溶液中加入36.8g肼水合物(721mmol,35.7mL,98.0%纯度)。添加后,将反应混合物在80℃下搅拌12小时。将反应混合物冷却至20℃并沉淀出大量黄色固体。将混合物减压浓缩以除去300mL乙醇并通过过滤收集固体。将滤饼用100mL乙醇洗涤,得到56.0g黄色固体。将产物用100mL水洗涤并干燥,得到36.0g(249mmol,74.2%产率)黄色固体状的标题化合物。
1H-NMR(400.2MHz,DMSO-d6):δ=8.19(s,1H),8.04(d,J=1.3Hz,1H),7.94(d,J=1.3Hz,1H),4.34(s,2H)。
步骤4:[(2S)-2-(叔丁氧基羰基氨基)丙酰基]2,2-二甲基丙酸酯
在20℃下,向50.0g N-(叔丁氧基羰基)-L-丙氨酸(264mmol)的600mL二氯甲烷的溶液中加入34.2mL三乙胺(245mmol)。在0℃滴加三甲基乙酰氯(31.9g,264mmol,32.5mL)。将混合物在20℃下搅拌16小时并且直接用于下一步骤而无需后处理或者纯化。
步骤5:(Z)-N-[(2S)-2-(叔丁氧基羰基氨基)丙酰基]环丙烷甲亚氨酸乙酯
在20℃下,向步骤4中制备的[(2S)-2-(叔丁氧基羰基氨基)丙酰基]2,2-二甲基丙酸酯的600mL二氯甲烷的溶液中加入36.7mL三乙胺(263mmol)。在20℃下分批加入环丙烷甲亚氨酸乙酯盐酸盐(39.4g,263mmol)。将混合物在20℃下搅拌16小时并且直接用于下一步骤而无需后处理或纯化。
步骤6:N-[(1S)-1-[2-(5-氯吡嗪-2-基)-5-环丙基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯
在25℃下,向100mL步骤5中制备的(Z)-N-[(2S)-2-(叔丁氧基羰基氨基)丙酰基]环丙烷甲酰亚氨酸乙酯的二氯甲烷溶液中加入11.7g(5-氯吡嗪-2-基)肼(80.9mmol)。将混合物在25℃搅拌16小时并变成棕色悬浮液。在20℃下,通过加入200mL饱和NaHCO3水溶液将反应混合物淬灭,并用二氯甲烷(3x 100mL)萃取。将合并的有机层用盐水(200mL)洗涤,经Na2SO4干燥,过滤并减压浓缩,得到残余物。将残余物通过柱色谱法(SiO2,石油醚/乙酸乙酯=30/1至0/1)纯化,得到13.0g为白色固体的标题化合物(35.6mmol,产率41.8%)。
1H-NMR(400.2MHz,DMSO-d6):δ=8.93(s,1H),8.77(s,1H),7.44(br d,J=7.3Hz,1H),5.37(quin,J=6.9Hz,1H),2.13-2.02(m,1H),1.39(d,J=7.3Hz,3H),1.30(s,8H),1.10-1.04(m,1H),1.00(dd,J=3.4,8.4Hz,2H),0.89-0.83(m,2H)。
步骤7:5-[5-[(1S)-1-(叔丁氧基羰基氨基)乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酸甲酯
在20℃下,向14.0g N-[(1S)-1-[2-(5-氯吡嗪-2-基)-5-环丙基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯的280mL甲醇的溶液中,加入10.7mL三乙胺(76.8mmol)和2.81gPd(dppf)Cl2(3.84mmol)。将悬浮液在真空下脱气并用CO吹扫数次。将混合物在CO(38.4mmol,860uL)(50psi)下在40℃下搅拌16小时并变成红褐色悬浮液。将反应混合物过滤,减压浓缩滤液,得到残余物。将残余物通过柱色谱法(SiO2,石油醚/乙酸乙酯=10/1至1/1)纯化,得到13.0g为白色固体的标题化合物(33.5mmol,产率86.3%),。
1H-NMR(400.2MHz,CDCl3):δ=9.33(s,1H),9.15(s,1H),5.84(br d,J=4.2Hz,1H),5.61-5.45(m,1H),4.07(s,3H),2.17-1.98(m,1H),1.53(d,J=6.7Hz,3H),1.43(br s,9H),1.12-0.98(m,4H)。
步骤8:N-[(1S)-1-[2-(5-氨基甲酰基吡嗪-2-基)-5-环丙基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯
在10℃下,向12.0g 5-[5-[(1S)-1-(叔丁氧基羰基氨基)乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酸甲酯(30.9mmol)的72mL四氢呋喃和24mL甲醇的溶液中,添加28.6mL NH3·H2O(185mmol,25%纯度)。将混合物在10℃下搅拌3小时并变成白色悬浮液。将反应混合物过滤并将固体用EtOAc在10℃下研磨15分钟,然后过滤以提供10.5g白色固体状的标题化合物(28.1mmol,91.0%产率)。
1H-NMR(400.2MHz,MeOD-d4):δ=9.30(s,1H),9.16(d,J=0.86Hz,1H),5.49(q,J=6.81Hz,1H),2.16-2.24(m,1H),1.67-1.81(m,3H),1.04-1.17(m,4H)。
步骤9:5-[5-[(1S)-1-氨基乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺盐酸盐
将三甲基氯硅烷(9.16g,84.3mmol,10.7mL)滴加至105mL 2,2,2-三氟乙醇中,并在10℃下搅拌30分钟。在20℃以下,将N-[(1S)-1-[2-(5-氨基甲酰基吡嗪-2-基)-5-环丙基-1,2,4-三唑-3-基]乙基]氨基甲酸叔丁酯(10.5g,28.1mmol)于105mL 2,2,2-三氟乙醇中滴加至上述溶液中。将混合物在10℃搅拌1小时。将反应混合物减压浓缩,得到粗产物。将粗产物用MTBE在10℃下研磨30分钟,然后过滤,得到8.52g为白色固体的标题化合物(27.5mmol,96.5%产率)。
1H-NMR(400.2MHz,MeOD-d4):δ=9.31(d,J=1.34Hz,1H),9.16(d,J=1.34Hz,1H),5.48(q,J=6.72Hz,1H),2.16-2.23(m,1H),1.75(d,J=6.72Hz,3H),1.08-1.12(m,4H)。
步骤10:5-[5-[(1S)-1-[[2,6-双(二氟甲基)吡啶-4-羰基]氨基]乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺
向99mg 5-[5-[(1S)-1-氨基乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺盐酸盐(0.319mmol)的2mL二氯甲烷的溶液中加入111μLN,N-二异丙基乙胺(0.638mmol),并将混合物在室温下搅拌30分钟。然后,加入100mg 2,6-双(二氟甲基)吡啶-4-甲酸(0.447mmol)、145mg HATU(0.383mmol)、78μL N,N-二异丙基乙胺(0.447mmol)和2mL二氯甲烷,然后将悬浮液在室温下搅拌16小时。减压除去溶剂,将残余物溶解在乙腈中,并通过反相色谱法(H2O/乙腈)纯化,得到105mg(0.219mmol,68.5%产率,100%纯度)的标题化合物。
ESI质量[m/z]:479.4[M+H]+
1H-NMR(400.2MHz,DMSO-d6),峰列表:δ=9.6885(3.0);9.6710(3.1);9.1153(6.8);9.1126(7.4);9.0504(7.4);9.0477(6.9);8.2782(3.1);8.1982(16.0);7.9025(3.0);7.2467(4.7);7.1106(10.7);6.9745(5.2);6.0466(0.4);6.0293(2.1);6.0120(3.3);5.9946(2.1);5.9772(0.4);3.3157(101.8);2.6901(2.6);2.6754(0.6);2.6712(0.8);2.6669(0.6);2.5242(2.7);2.5066(95.2);2.5022(126.2);2.4978(94.0);2.3334(0.6);2.3290(0.8);2.3248(0.6);2.1371(0.6);2.1249(1.2);2.1162(1.4);2.1042(2.6);2.0922(1.5);2.0837(1.4);2.0716(0.7);1.6330(11.6);1.6156(11.6);1.0244(3.4);1.0195(4.8);1.0033(3.4);0.9987(4.9);0.9807(0.6);0.9733(0.6);0.9641(0.4);0.9487(0.9);0.9364(0.9);0.9245(2.9);0.9190(1.6);0.9123(3.1);0.9068(2.6);0.8997(2.2);0.8876(1.9);0.8725(0.8);0.8632(0.5)。
分析方法
下文描述的分析方法涉及整个文件中的所有信息,除非在相应段落中单独描述了相应分析测定的方法。
质谱
[M+H]+或M-的测定通过LC-MS在酸性色谱条件下进行,使用1ml甲酸每升乙腈和0.9ml甲酸每升Millipore水作为洗脱液。使用Zorbax Eclipse Plus C18 50mm*2.1mm柱。柱温箱的温度为55℃。
1H-NMR数据使用配备有1.7mm TCI采样头的Bruker Avance III 400MHz光谱仪进行测定,以四甲基硅烷作为参比(0.00ppm),并且通常从溶剂CD3CN、CDCl3或d6-DMSO的溶液中记录测量值。或者,使用配备有5mm CPNMP采样头的Bruker Avance III 600MHz仪器或配备5mm TCI采样头的Bruker Avance NEO 600MHz仪器进行测量。通常测量是在采样头温度为298K的情况下进行的。其他测量温度会明确注明。
NMR峰列表法
所选实施例的1H-NMR数据以1H-NMR峰列表的形式记录。对于每个信号峰,列出了以ppm计的δ值和圆括号中的信号强度。δ值-信号强度数对通过分号彼此间隔列出。
因此,一个实施例的峰列表具有以下形式:
δ1(强度1);δ2(强度2);……;δi(强度i);……;δn(强度n)
尖峰信号的强度与1H-NMR谱的打印图像中以cm计的信号高度有关,并且显示了信号强度的真实比例。来自宽信号或者中间信号的数个峰以及它们与最强信号相比的相对强度可以显现出来。
四甲基硅烷或样品不含四甲基硅烷的情况下溶剂的化学位移用于校准1H谱的化学位移。因此,四甲基硅烷峰可以出现在1H-NMR峰列表中,但不是必须的。
1H-NMR峰列表相当于常规1H-NMR图谱,通常包含所有峰,这些峰也在常规1H-NMR说明中列出。
此外,它们可以显示溶剂信号、任选为本发明目的的化合物的立体异构体和/或杂质峰,如常规1H-NMR图谱。
1H-NMR溶剂信号、四甲基硅烷信号和相应溶剂中的水信号被排除在相对强度的校准之外,由于它们具有非常高的强度值。
平均而言,本发明化合物的立体异构体的峰和/或杂质的峰通常具有比本发明化合物的峰更低的强度(例如纯度>90%)。
这种立体异构体和/或杂质对于特定的制备方法来说是典型的。因此,相应的峰可以帮助通过“副产物指纹”识别制备方法的再现性。
使用已知方法(MestreC、ACD模拟,但也使用经验评估的期望值)计算目标化合物的峰的专业人员可根据需要任选地使用额外的强度过滤器来确定目标化合物的峰。该确定类似于常规1H-NMR说明中通常的峰选取。
使用的溶剂可以通过参数“溶剂”从JCAMP文件中读取,光谱仪频率通过“观察频率”读取,光谱仪类型通过“光谱仪/数据系统”读取。
13C-NMR数据可类似于1H-NMR数据报告为来自宽带解耦(broadband decoupled)的峰列表。13C-NMR溶剂信号和四甲基硅烷被排除在相对强度校准之外,由于这些信号可能具有非常高的强度。
使用峰列表描述NMR数据的其他详细信息公开于出版物Research DisclosureDatabase Number 564025的“Citation of NMR Peaklist Data within PatentApplications”中。
下表1中描述的本发明化合物同样是优选的式(I)化合物,其中R1为氢并且X为氧,并且其根据或类似于上述制备实施例获得。
表1
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1)“abs”表示化合物以对映体富集形式或纯物质形式获得,其中主要立体异构体具有图中所示的绝对构型。
2)“低T”表示测量是在260开尔文的温度下进行的。
3)所述质量对应于具有最高强度的[M+H]+离子的同位素谱峰。#表示记录了[M-H]-离子。
表2(中间体)
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1)“abs”表示化合物以对映体富集形式或纯物质形式获得,其中主要立体异构体具有图中所示的绝对构型。
2)所述质量对应于具有最高强度的[M+H]+离子的同位素谱峰。#表示记录了[M-H]-离子。
生物学实施例
微小扇头蜱(牛蜱属)(Rhipicephalus(Boophilus)microplus)–幼虫牛蜱的体外
接触测试(Parkhurst品系,抗合成拟除虫菊酯)
将9mg化合物溶解在1ml丙酮中,然后用丙酮稀释到所需浓度。将250μl测试溶液装入25ml玻璃试管中,并通过在振荡器上旋转和倾斜(2h,30rpm)而均匀分布在内壁上。在化合物浓度为900ppm、内表面为44.7cm2并且均匀分布的情况下,获得5μg/cm2的剂量。
在溶剂蒸发后,在每个试管中放入20-50只幼虫牛蜱(微小扇头蜱),用穿孔盖密封,并在培育箱中在27℃下和85%相对湿度下水平放置培育。48小时后,测定功效。将幼虫拍打至试管的底部,并记录消极的趋地行为。将以与未经处理的对照幼虫相当的方式爬回试管顶部的幼虫标记为存活,将没有以与未经处理的对照幼虫相当的方式爬回但以不协调方式移动或仅抽搐它们的腿的幼虫标记为将要死亡,将留在底部并且完全不动的蜱幼虫标记为死亡。
如果在5μg/cm2的化合物浓度下监测到至少80%的功效,则该化合物对微小扇头蜱显示出良好的功效。100%的功效表示所有幼虫均死亡或将要死亡;0%表示没有幼虫死亡或将要死亡。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出100%的良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-011、I-012、I-013、I-014、I-015、I-016、I-017、I-019、I-020、I-021、I-022、I-023、I-024、I-025、I-026、I-027、I-029、I-031、I-032、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-043、I-044、I-045、I-046、I-047、I-049、I-050、I-051、I-053、I-055、I-056、I-060、I-062、I-064、I-065、I-066、I-067、I-098。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出90%的良好活性:I-018、I-028。
微小扇头蜱(牛蜱属)-注射测试
溶剂:二甲基亚砜
为制备合适的活性化合物制剂,将10mg的活性化合物溶解于0.5ml溶剂中,并将浓缩物用溶剂稀释到所需浓度。
将1μl化合物溶液注射到5只成年饱食的雌蜱(微小扇头蜱)的腹部。将蜱转移到复制板上,并在气候室中培育。
在7天后,监测能育卵的产卵数。将没有明显能育性的卵储存在气候室中,直到约42天后孵化。100%的功效表示所有卵都是不育的;0%表示所有卵都是能育的。
在本测试中,例如,以下制备实施例的化合物在4μg/蜱的施用率下显示出100%的良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-083、I-084。
猫栉头蚤(Ctenocephalides felis)-成年猫蚤(cat flea)的体外接触测试
将9mg化合物溶解在1ml丙酮中,并用丙酮稀释到所需浓度。将250μl测试溶液装入25ml玻璃试管中,并通过在振荡器上旋转和倾斜(2h,30rpm)而均匀分布在内壁上。在化合物浓度为900ppm、内表面为44.7cm2并且均匀分布的情况下,获得5μg/cm2的剂量。
在溶剂蒸发后,在每个试管中放入5-10只成年猫蚤(猫栉头蚤),用穿孔盖密封,并在室温和相对湿度下水平放置培育。48小时后,测定功效。将猫蚤拍打至试管的底部,并在45-50℃的加热板上培育最多5分钟。将不能通过向上爬来逃离热量的不移动或以不协调方式移动的跳蚤标记为死亡或将要死亡。
如果在5μg/cm2的化合物浓度下监测到至少80%的功效,则化合物显示出对猫栉头蚤具有良好的功效。100%的功效表示所有跳蚤均死亡或将要死亡。0%表示没有跳蚤死亡或将要死亡。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出100%的良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-011、I-015、I-016、I-017、I-018、I-019、I-021、I-023、I-025、I-026、I-029、I-032、I-037、I-038、I-039、I-040、I-041,I-042、I-045、I-047、I-055、I-064、I-067。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出90%的良好活性:I-049、I-050。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出80%的良好活性:I-031、I-053。
猫栉头蚤-口服试验
溶剂:二甲亚砜
为制备合适的活性化合物制剂,将10mg活性化合物溶于0.5ml溶剂中,并用柠檬酸盐牛血将浓缩液稀释至所需浓度。
将约20只未喂食的成年猫蚤(猫栉头蚤)放入到一个顶部和底部用纱布覆盖的蚤室中。将底部用石蜡膜密封的室用血-化合物溶液填充,并将其放置在蚤室顶部,以便蚤能够吸食血液。将血室加热至37℃,而将蚤室保持在室温。
在2天后,测定以%计的杀死率。100%表示所有的蚤均已被杀死;0%意指没有蚤被杀死。
在本测试中,例如,以下制备实施例的化合物在100ppm的施用率下显示出100%的良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I 008、I-009、I-010。
血红扇头蜱(Rhipicephalus
sanguineus)-成年棕色狗蜱(dog
ticks)的体外接
触测试
将9mg化合物溶解在1ml丙酮中,然后用丙酮稀释到所需浓度。将250μl测试溶液装入25ml玻璃试管中,并通过在振荡器上旋转和倾斜(2h,30rpm)而均匀分布在内壁上。在化合物浓度为900ppm、内表面为44.7cm2并且均匀分布的情况下,获得5μg/cm2的剂量。
在溶剂蒸发后,在每个试管中放入5-10只成年棕色狗蜱(血红扇头蜱),用穿孔盖密封,并在室温和相对湿度下水平放置培育。48小时后,测定功效。将蜱拍打至试管的底部,并在45-50℃的加热板上培育最多5分钟。将不能通过向上爬来逃离热量的不移动或以不协调方式移动的蜱标记为死亡或将要死亡。
如果在5μg/cm2的化合物浓度下监测到至少80%的功效,则化合物显示出对血红扇头蜱具有良好的功效。100%的功效表示所有蜱均死亡或将要死亡。0%表示没有蜱死亡或将要死亡。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出100%的良好活性:I-001、I-002、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-011、I-012、I-013、I-014、I-015、I-016、I-017、I-018、I-019、I-021、I-023、I-024、I-025、I-026、I-029、I-036、I-037、I-038、I-039、I-040、I-041、I-042、I-045、I-047、I-049、I-053、I-064、I-067。
在本测试中,例如,以下制备实施例的化合物在1μg/cm2(=100g/ha)的施用率下显示出80%的良好活性:I-003、I-032、I-034、I-043、I-044、I-050、I-055。
黄瓜条叶甲(Diabrotica balteata)-喷洒测试
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水将浓缩液稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
将浸泡的小麦种子(小麦(Triticum aestivum))放置到填充有琼脂和一些水的多孔板中,并培育1天以发芽(5颗种子每孔)。向发芽的小麦种子喷洒含有所需浓度活性成分的试验溶液。其后,用10-20只带状黄瓜甲虫(黄瓜条叶甲)的幼虫侵染各单元。
7天后,测定以%计的功效。100%意指所有的幼苗都已经如未经处理、未被感染的对照组那样长大;0%意指没有幼苗生长。
在本测试中,例如,以下制备实施例的化合物在100g/ha(=32μg/孔)的施用率下显示出100%的良好活性:I-002、I-003、I-004、I-007、I-008、I-017、I-018、I-019、I-020、I-021、I-022、I-023、I-024、I-025、I-026、I-028、I-030、I-033、I-037、I-038、I-039、I-044、I-045、I-046、I-054、I-056、I-057、I-058、I-062、I-063、I-064、I-065、I-066、I-067、I-070、I-071、I-072、I-075、I-078、I-080、I-081、I-082、I-086、I-087、I-088、I-089、I-094、I-095、I-096、I-100、I-101、I-104、I-105。
在本测试中,例如,以下制备实施例的化合物在100g/ha(=32μg/孔)的施用率下显示出80%的良好活性:I-034、I-047、I-074、I-099。
桃蚜(Myzuspersicae)-喷洒试验
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
用所需浓度的活性成分制剂喷洒感染所有龄期的绿桃蚜(桃蚜)的大白菜(白菜(Brassica pekinensis))的叶盘。
5天后,测定以%计的死亡率。100%意指所有的蚜虫都已被杀死,0%意指没有蚜虫被杀死。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出100%的良好活性:I-005、I-006、I-012、I-016、I-017、I-018、I-020、I-037、I-040、I-041、I-102、I-104。
在该试验中,例如,制备实施例的以下化合物在100g/ha的施用率下显示出90%的良好活性:I-001、I-002、I-003、I-004、I-007、I-008、I-009、I-010、I-011、I-014、I-015、I-019、I-021、I-023、I-025、I-028、I-032、I-038、I-039、I-042、I-045、I-046、I-047、I-050、I-051、I-054、I-098、I-099、I-100、I-103、I-105。
桃蚜-口服测试
溶剂:100重量份丙酮
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用水将浓缩液稀释至所需浓度。
向微量滴定板中填充50μl化合物溶液,并加入150μl IPL41昆虫培养基(33%+15%糖),以获得每孔200μl的总体积。其后,用石蜡膜密封所述板,绿桃蚜(桃蚜)的混合种群可通过石蜡膜吸取化合物制剂。
5天后,测定以%计的死亡率。100%意指所有的蚜虫都已被杀死,0%意指没有蚜虫被杀死。
在本测试中,例如,以下制备实施例的化合物在20ppm的施用率下显示出100%的良好活性:I-004、I-018、I-030、I-043、I-048、I-049、I-050、I-051、I-055。
稻绿蝽(Nezaraviridula)-喷洒试验
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水将浓缩液稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
用含有所需浓度的活性成分的试验溶液喷洒经南方绿椿象(稻绿蝽)的幼虫侵染的大麦植株(大麦(Hordeum vulgare))。
4天后,测定以%计的死亡率。100%意指所有的椿象都已被杀死;0%意指没有椿象被杀死。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下显示出100%的良好活性:I-001、I-008、I-009、I-010、I-011、I-012、I-015、I-016、I-017、I-018、I-019、I-020、I-021、I-022、I-025、I-026、I-028、I-033、I-034、I-037、I-038、I-040、I-041、I-042、I-043、I-047、I-048、I-049、I-050、I-054、I-055、I-067、I-069、I-070、I-073、I-076、I-077、I-078、I-079、I-080、I-086、I-087、I-088、I-091、I-092、I-093、I-094、I-095、I-098、I-099、I-100、I-101、I-102、I-103。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下显示出90%的良好活性:I-014、I-030、I-051、I-068、I-071、I-072、I-082。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下显示出70%的良好活性:I-004。
褐飞虱(Nilaparvatalugens)-喷洒试验
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
将稻植物(水稻(Oryza sativa))用含有所需浓度的活性成分的试验溶液喷洒,并用褐飞虱侵染植物。
4天后,测定以%计的死亡率。100%意指所有的飞虱都已被杀死;0%意指没有飞虱被杀死。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下显示出100%的良好活性:I-001、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-012、I-014、I-015、I-016、I-017、I-018、I-019、I-020、I-021、I-023、I-024、I-025、I-026、I-032、I-037、I-038、I-040、I-041、I-042、I-043、I-045、I-047、I-048、I-049、I-050、I-051、I-054、I-055、I-067、I-073、I-098。
在该试验中,例如,以下制备实施例的化合物在500g/ha的施用率下显示出90%的良好活性:I-002、I-031、I-069、I-071、I-072。
草地贪夜蛾(Spodoptera
frugiperda)-喷洒试验
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
用所需浓度的活性成分制剂喷洒玉米(玉米(Zea mays))的叶片部分。干燥后,用秋粘虫幼虫(草地贪夜蛾)侵染所述叶片部分。
7天后,测定以%计的死亡率。100%意指所有的毛虫都已被杀死;0%意指没有毛虫被杀死。
在该试验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出100%的良好活性:I-001、I-002、I-003、I-004、I-005、I-006、I-007、I-008、I-009、I-010、I-011、I-012、I-013、I-014、I-015、I-016、I-018、I-019、I-021、I-022、I-023、I-024、I-025、I-026、I-028、I-029、I-031、I-032、I-033、I-034、I-035、I-036、I-037、I-038、I-039、I-040、I-044、I-045、I-046、I-047、I-050、I-053、I-054、I-055、I-056、I-057、I-058、I-060、I-061、I-062、I-063、I-064、I-065、I-066、I-067、I-068、I-069、I-070、I-071、I-072、I-073、I-074、I-075、I-076、I-077、I-078、I-079、I-081、I-082、I-084、I-086、I-089、I-090、I-093、I-099、I-100、I-101、I-102、I-103、I-105。
在该试验中,例如,以下制备实施例的化合物在100g/ha的施用率下显示出83%的良好活性:I-027、I-094。
埃及伊蚊(Aedes aegypti)测试(AEDSAE表面处理&接触试验)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为制备含足够的活性成分的溶液,需要将试验化合物溶于该溶剂混合物(丙酮,2mg/ml/RME 2000ppm)中。将该溶液吸移到釉面砖上,并且在丙酮蒸发后,将物种埃及伊蚊MONHEIM种的成年蚊放置到干燥后的表面上。暴露时间为30分钟。在昆虫与经处理的表面接触24小时后,测定以百分比(%)计的死亡率。100%的死亡率意指所有试验的昆虫均死亡,而0%意指没有昆虫死亡。
在该试验中以下实施例在20mg/m2的表面浓度下显示出80-100%的功效:I-002、I-007、I-008、I-009、I-021、I-022、I-023、I-025、I-037、I-038、I-039。
在该试验中以下实施例在4mg/m2的表面浓度下显示出80-100%的功效:I-002、I-007、I-008、I-009、I-019、I-021、I-022、I-023、I-025、I-037、I-038。
不吉按蚊(Anopheles
funestus)测试(ANPHFU表面处理&接触试验)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为制备含足够的活性成分的溶液,需要将试验化合物溶于该溶剂混合物(丙酮,2mg/ml/RME 2000ppm)中。将该溶液吸移到釉面砖上,并且在丙酮蒸发后,将物种不吉按蚊FUMOZ-R种(Hunt等人,Med.Vet.Entomol.2005年9月;19(3):271-275)的成年蚊放置到干燥后的表面上。暴露时间为30分钟。在昆虫与经处理的表面接触24小时后,测定以百分比(%)计的死亡率。100%的死亡率意指所有试验的昆虫均死亡,而0%意指没有昆虫死亡。
在本测验中以下实施例在20mg/m2的表面浓度下显示出85-100%的功效:I-002、I-009。
在本测验中以下实施例在4mg/m2的表面浓度下显示出85-100%的功效:I-002、I-009。
致倦库蚊(Culex quinquefasciatus)测试(CULXFA表面处理&接触试验)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为制备含足够的活性成分的溶液,需要将试验化合物溶于该溶剂混合物(丙酮,2mg/ml/RME 2000ppm)中。将该溶液吸移到釉面砖上,并且在丙酮蒸发后,将物种致倦库蚊P00种的成年蚊放置到干燥后的表面上。暴露时间为30分钟。在昆虫与经处理的表面接触24小时后,测定以百分比(%)计的死亡率。100%的死亡率意指所有试验的昆虫均死亡,而0%意指没有昆虫死亡。
在本测验中以下实施例在20mg/m2的表面浓度下显示出80-100%的功效:I-002、I-007、I-008、I-009、I-021、I-022、I-023、I-025、I-037、I-038、I-039。
在本测验中以下实施例在4mg/m2的表面浓度下显示出80-100%的功效:I-007、I-008、I-009、I-021、I-022、I-023、I-038、I-039。
家蝇(Musca domestica)测试(MUSCDO表面处理&接触试验)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为制备含足够的活性成分的溶液,需要将试验化合物溶于该溶剂混合物(丙酮,2mg/ml/RME 2000ppm)中。将该溶液吸移到釉面砖上,并且在丙酮蒸发后,将物种家蝇WHO-N种的成年蝇放置到干燥后的表面上。暴露时间为30分钟。在昆虫与经处理的表面接触24小时后,测定以百分比(%)计的死亡率。100%的死亡率意指所有试验的昆虫均死亡,而0%意指没有昆虫死亡。
在本测试中以下实施例在20mg/m2的表面浓度下显示出80-100%的功效:I-002、I-007、I-008、I-009、I-021、I-022、I-038、I-039、I-023、I-025、I-037。
在本测试中以下实施例在4mg/m2的表面浓度下显示出80-100%的功效:I-007、I-008、I-009、I-009、I-021、I-022、I-038、I-039、I-023。
德国小蠊(Blattella
germanica)测试(BLTTGE表面处理&接触试验)
溶剂:丙酮+2000ppm菜籽油甲酯(RME)
为制备含足够的活性成分的溶液,需要将试验化合物溶于该溶剂混合物(丙酮,2mg/ml/RME 2000ppm)中。将该溶液吸移到釉面砖上,并且在丙酮蒸发后,将物种德国小蠊PAULINIA种的成年动物放置到干燥后的表面上。暴露时间为30分钟。
在昆虫与经处理的表面接触24小时后,测定以百分比(%)计的死亡率。100%的死亡率意指所有试验的昆虫均死亡,而0%意指没有昆虫死亡。
在本测试中以下实施例在20mg/m2的表面浓度下显示出80-100%的功效:I-002、I-007、I-008、I-009、I-019、I-021、I-022、I-023、I-025、I-037。
在本测试中以下实施例在4mg/m2的表面浓度下显示出80-100%的功效:I-007、I-008、I-009、I-021、I-022、I-023、I-025。
比较实施例
桃蚜喷洒试验(MYZUPE)
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
用所需浓度的活性成分制剂喷洒被所有阶段的绿桃蚜(桃蚜)侵染的大白菜(白菜)的叶盘。
经过指定的时间后,测定以%计的死亡率。100%意指所有的蚜虫都已被杀死;0%意指没有蚜虫被杀死。
在本次测试中,例如,与现有技术相比,以下制备实施例的化合物表现出更高水平的活性:参见表格。
草地贪夜蛾-喷洒试验(SPODFR)
溶剂:78.0重量份丙酮
1.5重量份二甲基甲酰胺
乳化剂:烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份活性化合物与所述量的溶剂混合,并用含有浓度为1000ppm的乳化剂的水稀释至所需浓度。通过用含有乳化剂的水稀释来制备其他试验浓度。
将玉米(Zea mays)叶片部分喷洒所需浓度的活性成分制剂。一旦干燥,将叶片部分使用秋粘虫幼虫(草地贪夜蛾)侵染。
经过指定的时间后,测定以%计的死亡率。100%意指所有的毛虫都已被杀死;0%意指没有毛虫被杀死。
在本次测试中,例如,与现有技术相比,以下制备实施例的化合物表现出更高水平的活性:参见表格。
表3-比较实施例
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Dat=处理后的天数
Claims (16)
1.式(I)的化合物,
其中,
X为O或S;
R1为氢;
R2为选自以下的子结构Q1和Q2,其中连至C=X-基团的键用#标记:
其中
R21为卤素、-CN、-SF5、C1-C3卤代烷基、C1-C3卤代烷氧基、C1-C3卤代烷硫基、C1-C3卤代烷基亚磺酰基、C1-C3卤代烷基磺酰基、C1-C3烷硫基、C1-C3烷基亚磺酰基、C1-C3烷基磺酰基、C3-C4环烷硫基、C3-C4环烷基亚磺酰基、C3-C4环烷基磺酰基;或苯磺酰基,其中苯基任选地被一至两个选自卤素、-CN、甲基、三氟甲基和三氟甲氧基的取代基取代;或环丙基,其中环丙基任选地被一至两个选自卤素、-CN、甲基和三氟甲基的取代基取代;
R22为氢、卤素、-CN、C1-C3卤代烷基、C1-C3卤代烷氧基或C1-C3卤代烷基磺酰基;
R31为氢、C1-C3烷基或C3-C6环烷基;
R32为氢、C1-C3烷基或C3-C6环烷基,其中C1-C3烷基和C3-C6环烷基任选地被一至三个选自卤素、-CN、C3-C6环烷基和C1-C3烷氧基的取代基取代;
R4为氢、C1-C3烷基、C1-C3烷氧基或C3-C4环烷基。
2.根据权利要求1的化合物,其中
X为O或S;
R1为氢;
R2选自以下子结构Q1和Q2,其中连接至C=X-基团的键用#标记:
其中
R21为氟、氯、溴、碘、-CN、-SF5、环丙基、1-甲基环丙基、1-氰基环丙基、二氟甲基、1,1-二氟乙基、三氟甲基、氯二氟甲基、2-氟丙-2-基、二氟甲氧基、三氟甲氧基、二氟甲硫基、三氟甲硫基、二氟甲基磺酰基、三氟甲基磺酰基、甲基硫烷基、甲基亚磺酰基、甲基磺酰基、乙基磺酰基、环丙基磺酰基或4-氯苯基-磺酰基;
R22为氢、氟、氯、溴、碘、-CN、二氟甲基、三氟甲基、二氟甲氧基、三氟甲氧基、1,1,2,2-四氟乙氧基、二氟甲基磺酰基或三氟甲基磺酰基;
R31为氢、甲基、乙基或环丙基;
R32为氢、C1-C3烷基或环丙基,其中C1-C3烷基和环丙基任选地被1至3个选自氟、氯、-CN、环丙基和甲氧基的取代基取代;R4 R为氢、甲基、甲氧基或环丙基。
3.根据权利要求1或2的化合物,其中
X为O;
R1为氢;
R2为3-氯-5-(三氟甲基)苯基、3,5-双(二氟甲基)苯基、3,5-双(三氟甲基)苯基、3-溴-5-(2-氟丙-2-基)苯基、3-氟-5-(三氟甲氧基)苯基、3-溴-5-(三氟甲氧基)苯基、3,5-双(二氟甲氧基)苯基、3,5-双(三氟甲氧基)苯基、3-环丙基-5-(三氟甲氧基)苯基、3-(1-甲基环丙基)-5-(三氟甲氧基)苯基、3-(1-氰基环丙基)-5-(三氟甲氧基)苯基、3-氯-5-(五氟-λ6-硫烷基)苯基、3-溴-5-(五氟-λ6-硫烷基)苯基、3-氯-5-甲基磺酰基苯基、3-甲基磺酰基-5-(三氟甲基)苯基、3-甲基磺酰基-5-(三氟甲氧基)苯基、3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯基、3-(二氟甲基磺酰基)-5-(三氟甲氧基)苯基或2,6-双(二氟甲基)吡啶-4-基;
R31为氢、甲基或乙基;
R32为氢、甲基、氰基甲基、氰基乙基、2,2-二氟乙基、环丙基或环丙基甲基;
R4为氢、甲基、甲氧基或环丙基。
4.化合物
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-环丙基-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(3-甲基-5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(3-甲基-5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-甲基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸,
5-(5-{(1S)-1-[3,5-双(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-[5-[(1S)-1-氨基乙基]-3-环丙基-1,2,4-三唑-1-基]吡嗪-2-甲酰胺盐酸盐,
5-(5-{(1S)-1-[(叔丁氧基羰基)氨基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-{5-[(1S)-1-氨基乙基]-3-环丙基-1H-1,2,4-三唑-1-基}吡嗪-2-甲酸甲酯盐酸盐,
5-(3-环丙基-5-{(1S)-1-[3-(甲基磺酰基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3,5-双(二氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
5-(5-{(1S)-1-[3-(1-氰基环丙基)-5-(三氟甲氧基)苯甲酰胺基]乙基}-3-环丙基-1H-1,2,4-三唑-1-基)吡嗪-2-甲酸甲酯,
3-甲基磺酰基-5-(1,1,2,2-四氟乙氧基)苯甲酸。
5.制剂,尤其是农业化学制剂,其包含至少一种根据权利要求1至3中任一项所述的式(I)化合物。
6.根据权利要求5的制剂,进一步包含至少一种增量剂和/或至少一种表面活性物质。
7.根据权利要求5或6的制剂,其特征在于式(I)化合物与至少一种其他活性化合物混合。
8.防治害虫的方法,尤其是防治动物害虫的方法,其特征在于使根据权利要求1至3中任一项的式(I)化合物或根据权利要求5至7中任一项的制剂作用于害虫和/或它们的生境,然而排除通过手术或疗法对动物体进行治疗的方法以及对动物体实施的诊断方法。
9.根据权利要求8的方法,其特征在于所述害虫为动物害虫并且包括昆虫、蛛形纲动物或线虫,或者在于所述害虫为昆虫、蛛形纲动物或线虫。
10.根据权利要求1至3中任一项所述的式(I)化合物或根据权利要求5至7中任一项所述的制剂用于防治动物害虫的用途,然而排除通过手术或疗法对动物体进行治疗的方法以及对动物体实施的诊断方法。
11.根据权利要求10的用途,其特征在于所述动物害虫包括昆虫、蛛形纲动物或线虫,或者在于所述动物害虫为昆虫、蛛形纲动物或线虫。
12.根据权利要求10或11的用途,其用于作物保护。
13.根据权利要求10或11的用途,其用于动物健康领域。
14.根据权利要求10或11的化合物或盐在病媒防治中的用途。
15.保护种子或发芽植物免受害虫、尤其是动物害虫侵害的方法,包括使种子与根据权利要求1至3中任一项的式(I)的化合物或根据权利要求5至7中的任一项的制剂接触的方法步骤。
16.种子,其通过根据权利要求15的方法获得。
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