CN108349953A - 杀虫组合物和方法 - Google Patents
杀虫组合物和方法 Download PDFInfo
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- CN108349953A CN108349953A CN201680067009.1A CN201680067009A CN108349953A CN 108349953 A CN108349953 A CN 108349953A CN 201680067009 A CN201680067009 A CN 201680067009A CN 108349953 A CN108349953 A CN 108349953A
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Classifications
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Plural Heterocyclic Compounds (AREA)
Abstract
取代的咪唑和取代的吡唑化合物及由其衍生的组合物可用于防治害虫。合适的咪唑化合物可以是2,4,5‑三苯基‑1H‑咪唑的类似物,其中C‑2苯基具有至少一个取代,C‑4和C‑5苯基任选被取代,并且N‑1是未取代的。合适的吡唑化合物可以具有1,3,4‑取代模式,其中在N‑1处存在任选取代的芳基或任选取代的烷基,在C‑3处存在任选取代的芳基或任选取代的杂芳基,并且在C‑4处存在仲酰胺基团。这些化合物和由其衍生的组合物可以施用于植物、种子、土壤或昆虫以防治各种害虫。
Description
相关申请的交叉引用
本申请根据35U.S.C.§119要求于2015年11月18日提交的美国临时专利申请62/256,867的优先权权益,并且所述申请通过引用整体并入本文。
关于由联邦政府资助研究或研发的声明
不适用。
领域
本申请总体上涉及昆虫防治,并且更具体地涉及使用取代的咪唑和取代的吡唑化合物用于防治害虫的组合物和方法。
背景
害虫可在农业中造成重大损失,这可能会影响粮食产量,并导致消费者成本增加。有效防治无脊椎害虫可有助于更高效的作物生产。
在害虫中尤其不期望的是那些能够显著影响重要中耕作物产量的害虫,所述作物包括例如玉米、大豆、棉花和某些其它类型的蔬菜。可能对这些作物具有破坏性影响的害虫的例子包括但不限于秋夜蛾、西方玉米根虫、小菜蛾、西方牧草盲蝽(Western tarnishedplantbug)和大豆夜蛾。
同样地,不是作为食物来源栽培的观赏植物或其它类型的植物可能会受到一系列害虫的影响。不同的害虫可能会影响这些类型的植物。
害虫也可能对人类和动物造成滋扰或健康危害。由于他们接近以昆虫为目标的农产品,所以农业工作者通常会受到特别的影响。蚊子是可能对人类和动物造成滋扰或健康危害的害虫的众多例子之一。
尽管可以在市场上买到用于防治害虫的产品,但仍然需要更有效、成本更低、对环境更安全和/或显示新的作用模式的新制剂。鉴定具有改善的抗虫活性的新化合物可能是寻找具有改善的杀虫活性的制剂的驱动因素。
概述
本文描述了表现出杀虫活性的化合物。本文所述的化合物可以用于例如制备组合物并根据下文详细阐述的防治害虫的方法来使用。更具体地说,本文描述了使用取代的咪唑和取代的吡唑化合物用于防治害虫的组合物和方法。
在一些实施方案中,本公开的方法包括向植物、种子、土壤或昆虫施用包含式I的化合物、其互变异构体或其盐的组合物
R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基。R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基。R1-R5中至少一者不是氢。R6和R7独立地选自氢、卤素和烷基。R8选自氢、烷基和任选取代的酰基苯基。
还描述了包含式I的化合物、其互变异构体(tautometer)或其盐的处理组合物。
处理过的种子可通过向种子施用式I的化合物、其互变异构体或其盐来制得,其中处理过的种子包含式I的化合物。
在一些或其它示例性实施方案中,本公开的方法包括向植物、种子、土壤或昆虫施用包含式II的化合物或其盐的组合物
R10选自任选取代的芳基和任选取代的烷基。R11选自任选取代的芳基和任选取代的杂芳基。R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基。Z是C1-C6烷基或键。
还描述了包含式II的化合物或其盐的处理组合物。
处理过的种子可通过向种子施用式II的化合物或其盐来制得,其中处理过的种子包含式II的化合物。
附图简述
不适用。
详述
本文描述了表现出杀虫活性的化合物。本文所述的化合物可以用于例如制备组合物并根据下文详细阐述的防治害虫的方法来使用。更具体地说,本文描述了使用取代的咪唑和取代的吡唑化合物用于防治害虫的组合物和方法。
如本文所用,术语“害虫”是指侵扰植物或种植地点的任何昆虫,或者是对人或动物有害的昆虫。下文提供害虫的更具体实例。
本公开提供了许多对防治害虫具有有益活性的化合物。属于本文讨论的类型的取代的咪唑和取代的吡唑化合物可用于此目的。这些化合物可单独使用或彼此组合用于防治害虫。取决于化合物中存在的取代基,一些害虫可优先于其它害虫被靶向。
在一些实施方案中,适用于防治害虫的化合物可以是式I的化合物、其互变异构体或其盐
R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基。R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基。R1-R5中至少一者不是氢。R6和R7独立地选自氢、卤素和烷基。R8选自氢、烷基和任选取代的酰基苯基。R9选自氢和烷基。
在一些或其它实施方案中,适用于防治害虫的化合物可以是式II的化合物或其盐。
R10选自任选取代的芳基和任选取代的烷基。R11选自任选取代的芳基和任选取代的杂芳基。R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基。Z是C1-C6烷基或键。
如本文所用,术语“互变异构体”是指以至少两种形式存在的任何化合物,所述形式容易相互转化,并且在至少两种形式之间建立平衡状态。
如本文所用,术语"卤素"是指氟、氯、溴或碘的任何基团。
如本文所用,术语“烷基”本身或作为另一基团的一部分是指具有多达10个碳的直链和支链基团,其可任选独立地被取代。C1-C10烷基的非限制性实例包括甲基、乙基、丙基、异丙基、丁基、仲丁基、叔丁基、戊基、异戊基、己基、庚基和辛基。在本公开的一些实施方案中,术语“烷基”本身或作为另一基团的一部分是指包含一至六个碳原子或一至三个碳原子的直链或支链基团。
如本文所用,术语“卤代烷基”本身或作为另一基团的一部分是指被至少一个卤素取代的烷基。卤代烷基的非限制性实例包括三氟甲基和2,2,2-三氟乙基。
如本文所用,术语“烷氧基”本身或作为另一基团的一部分是指通过氧原子附接至母体分子实体的烷基。烷氧基的非限制性实例包括甲氧基、乙氧基、丙氧基、2-丙氧基、1-丁氧基、2-丁氧基、叔丁氧基、1-戊氧基、2-戊氧基、3-戊氧基、1-己氧基、2-己氧基和3-己氧基。
如本文所用,术语“硫代烷基”是指烷氧基的硫类似物,其中烷基单独或作为另一基团的一部分通过硫原子附接至母体分子实体上。
如本文所用,术语“卤代烷氧基”本身或作为另一基团的一部分是指其中所附接的烷基进一步被至少一个卤素取代的烷氧基。卤代烷氧基的非限制性实例包括三氟甲氧基、2,2-二氯乙氧基和2,2,2-三氟乙氧基。
如本文所用,术语“环烷基”是指形成包含3至8个碳原子或6至10个碳原子的闭环的烷基,其可以任选被取代。环烷基基团的非限制性实例包括环丙基、环丁基、环戊基、环己基、甲基环己基和环庚基。术语“环烷基”进一步是指任何单环、双环和多环含碳环。
如本文所用,术语“任选取代的”是指可以作为连接至含碳环或链的侧基存在的部分。在一些实施方案中,任选的取代可以是包含至少一个杂原子的侧基。如本文所用,术语“杂原子”是指氧、氮、硫或卤素原子。
如本文所用,术语“杂环烷基”是指含有一个或多个选自O、S和N的杂原子的饱和或部分饱和的单环或双环烃,所述杂原子取代含碳环中的一个或多个碳原子。杂环烷基可以经由任何碳原子或氮原子(如果存在)连接至母体分子实体。杂环烷基的非限制性实例包括但不限于4元环,例如氮杂环丁烷基和氧杂环丁基;5元环,例如四氢呋喃基、二氧杂环戊烯基(dioxolinyl)、吡咯烷基、吡咯烷酮基(pyrrolidinonyl)、咪唑烷基、吡唑烷基和吡咯啉基;6元环,例如四氢吡喃基、四氢硫代吡喃基、哌啶基、吗啉基、二噻烷基、硫代吗啉基、哌嗪基和三噻烷基;或7元环,例如二氮杂环庚烷环。
如本文所用,术语“芳基”本身或作为另一基团的一部分是指含有6至14个碳原子的单环、二环或三环芳族基团。常见的芳基包括C6-C14芳基,特别是C6-C10芳基。C6-C14芳基的非限制性实例包括苯基、萘基、菲基、蒽基、茚基、薁基(azulenyl)、联苯基、亚联苯基和芴基。
如本文所用,术语“杂芳基”本身或作为另一基团的一部分是指具有5至14个环原子和6、10或14个在环状阵列中共享的π电子的环状部分,其中1、2或3个环原子是氧原子、氮原子和/或硫原子,其余的环原子是碳原子。杂芳基的非限制性实例包括噻吩基(噻吩基)、苯并[b]噻吩基、萘并[2,3-b]噻吩基、噻蒽基、呋喃基(呋喃基)、吡喃基、异苯并呋喃基、色烯基、呫吨基、吩噻噁基(phenoxanthinyl)、吡咯基,包括但不限于2H吡咯基、咪唑基、吡唑基、吡啶基(吡啶基),包括但不限于2-吡啶基、3-吡啶基和4-吡啶基、吡嗪基、嘧啶基、哒嗪基、吲嗪基、异吲哚基、3H-吲哚基、吲哚基、吲唑基、嘌呤基、4H-喹嗪基、异喹啉基、喹啉基、酞嗪基、萘啶基、喹唑啉基、噌啉基、蝶啶基、咔唑基、β-咔啉基、菲啶基、吖啶基(acrindinyl)、嘧啶基、菲咯啉基、吩嗪基、异噻唑基、吩噻嗪基、异噁唑基、呋咱基、吩噁嗪基、1,4-二氢喹喔啉-2,3-二酮、7-氨基异香豆素、吡啶并[1,2-α]嘧啶-4-酮、吡唑并[1,5-α]嘧啶基,包括但不限于吡唑并[1,5-α]嘧啶-3-基、1,2-苯并异噁唑-3-基、苯并咪唑基、2-羟吲哚基和2-氧代苯并咪唑基。在杂芳基于环中含有氮原子的情况下,氮原子可以任选地为N-氧化物形式,例如吡啶基N-氧化物、吡嗪基N-氧化物或嘧啶基N-氧化物。
如本文所用,术语“烯基”是指其中至少一个碳-碳双键已经替代碳-碳单键的直链或支链烷基。该至少一个碳-碳双键可以在任何位置并且是E或Z构型的。烯基的非限制性实例包括乙烯基、E-和Z-丙烯基、2-丙烯基(烯丙基)、E-和Z-丁烯基、E-和Z-异丁烯基、E-和Z-戊烯基、E-和Z-己烯基、E,E-、E,Z-、Z,E-、Z,Z-己二烯基等。
如本文所用,术语“炔基”是指其中至少一个碳-碳三键已经替代碳-碳单键的直链或支链烷基。炔基的非限制性实例包括CH2-CH≡CH(炔丙基)、CH2-C≡C-CH3,和CH2-C≡C-CH(CH3)-CH2-CH3
如本文所用,术语“烯氧基”和“炔氧基”分别是指通过氧原子附接至母体分子实体上的烯基或炔基。
如本文所用,术语“酰基苯基”是指通过羰基部分附接至母体分子实体的苯基。
如本领域普通技术人员将理解的,N-未取代的咪唑化合物在1H和3H形式之间是互变异构和相互转化的。1H和3H形式之间的平衡分布可以取决于许多因素,包括例如pH、温度和存在于咪唑基团上的取代基的类型。因此,应该理解,本文对具有式I的结构的化合物的任何提及也等同地指式I’的互变异构3H结构或具有式I和I’的结构的化合物的平衡混合物。
认为具有式II的结构的化合物基本上不是互变异构的。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基和炔氧基。在一些或其它实施方案中,组合物包含式I的化合物、互变异构体或盐,其中、R1、R2和R3独立地选自氢、卤素、烷基、烷氧基和炔氧基。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1、R2和R3各自是烷基,并且在更特定的实施方案中,R1、R2和R3各自是甲基。在更特定的实施方案中,R1、R2和R3各自是甲基且R4-R9各自是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1和R2各自是烷基,并且在更特定的实施方案中,R1和R2各自是甲基。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1和R3各自是卤素,或R1和R2各自是卤素。在更特定的实施方案中,R1和R3各自是氯,或R1是氯且R3是氟,或R1和R2各自是氯。在更特定的实施方案中,R1和R3各自是氯,R6和R7各自是甲基,并且R2、R4、R5、R8和R9各自是氢;或R1是氯,R3是氟,R6和R7各自是甲基,并且R2、R4、R5、R8和R9各自是氢;或R1和R2各自是氯,R6是氯,并且R3、R4、R5、R7、R8和R9各自是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R4和R5中的一者或两者是卤素,并且在更特定的实施方案中,R4和/或R5是氯或氟。在更特定的实施方案中,R4是氟,R9是酰基苯基或酰基(4-氟苯基),并且R1-R3和R5-R8是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1和R2中的至少一者是烷氧基,并且在更特定的实施方案中,R1和R2各自是甲氧基,或R1是乙氧基,或R2是甲氧基。在更特定的实施方案中,R1和R2各自是甲氧基,并且R3-R9是氢;或R1是乙氧基且R2-R9是氢;或R2是甲氧基,R4和R5各自是甲氧基,并且R1、R3和R6-R9是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1是炔氧基,并且在更特定的实施方案中,R1是炔丙氧基(propargyloxy)。在更特定的实施方案中,R1是炔丙氧基且R2-R9是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R2是硫代烷基,并且在更特定的实施方案中,R2是硫代甲基。在更特定的实施方案中,R2是硫代甲基,R8是甲基,并且R1、R3-R7和R9是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1是氢,或R2是氢,或R3是氢。在一些实施方案中,R2和R3各自是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R4和R5是烷氧基,并且在更特定的实施方案中,R4和R5是甲氧基。在其它实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R1、R2和R4是烷氧基,并且在更特定的实施方案中,R1、R2和R4是甲氧基。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R6和R7是烷基,并且在更特定的实施方案中,R6和R7各自是甲基。在更特定的实施方案中,R6和R7各自是甲基且R8是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R6是卤素且R7是氢,并且在更特定的实施方案中,R6是氯且R7是氢。在更特定的实施方案中,R6是氯且R7和R8是氢。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R9是烷基,并且在更特定的实施方案中,R9是甲基。
在一些实施方案中,组合物包含式I的化合物、互变异构体或盐,其中R9是任选取代的酰基苯基,并且在更特定的实施方案中,R9是酰基苯基或酰基(4-氟苯基)。
在一些实施方案中,组合物包含式II的化合物或盐,其中R10是任选取代的芳基,并且在更特定的实施方案中,R10是任选取代的苯基,或R10是甲苯基。在更特定的实施方案中,R10是对甲苯基。在更特定的实施方案中,R10是对甲苯基,R11是苯基,R12是烯丙基,并且Z是键;或R10是苯基,R11是2-噻吩基,R12是2-甲基环己基,并且Z是键。
在一些实施方案中,组合物包含式II的化合物或盐,其中R10是烷基或任选取代的烷基,并且在更特定的实施方案中,R10是甲基。在更特定的实施方案中,R10是甲基且R11是2-氯苯基。在又一些更特定的实施方案中,R10是甲基,R11是2-氯苯基,R12是乙氧基,并且Z是C2烷基;或R10是甲基,R11是2-氯苯基,R12是四氢呋喃-2-基,并且Z是C2烷基;或R10是甲基,R11是2-氯苯基,R12是四氢噻喃-4-基,并且Z是键。
在一些实施方案中,组合物包含式II的化合物或盐,其中R11是任选取代的芳基,并且在更特定的实施方案中,R11是苯基或卤代苯基。在更特定的实施方案中,R11是氯苯基,并且在又一些更具体的实施方案中,R11是2-氯苯基。
在一些实施方案中,组合物包含式II的化合物或盐,其中R11是任选取代的杂芳基,并且在更特定的实施方案中,R11是噻吩基。在更特定的实施方案中,R11是2-噻吩基。
在一些实施方案中,组合物包含式II的化合物或盐,其中R12是任选取代的完全饱和的环烷基,并且在更特定的实施方案中,R12是任选取代的完全饱和的C3-C6环烷基。在更特定的实施方案中,R12是2-甲基环己基,并且在更特定的实施方案中,R12是2-甲基环己基并且Z是键。
在一些实施方案中,组合物包含式II的化合物或盐,其中R12是任选取代的杂环烷基,并且在更特定的实施方案中,R12是四氢呋喃基或四氢噻喃基。在更特定的实施方案中,R12是四氢呋喃-2-基,并且Z是C2烷基;或R12是四氢-2H-噻喃-4-基并且Z是键。
在一些实施方案中,组合物包含式II的化合物或盐,其中R12是烯基,并且在更特定的实施方案中,R12是烯丙基。在更特定的实施方案中,R12是烯丙基并且Z是键。
在一些实施方案中,组合物包含式II的化合物或盐,其中R12是烷氧基,并且在更特定的实施方案中,R12是乙氧基。在更特定的实施方案中,R12是乙氧基并且Z是C2烷基。
在一些实施方案中,组合物包含式II的化合物或盐,其中Z是C1-C6烷基,并且在一些实施方案中,Z是C1-C3烷基。在更特定的实施方案中,Z是直链饱和亚烷基部分,具体为二价亚甲基、亚乙基、亚丙基、亚丁基、亚戊基或亚己基部分。
在一些实施方案中,组合物包含式II的化合物或盐,其中Z是键。如本文所用,术语“键”是指式II的酰胺氮原子与包含R12的部分之间的直接连接。也就是说,在酰胺氮原子和R12之间存在键的实施方案中,没有插入的桥接原子。
在非限制性实施方案中,符合可适用于本公开的各种实施方案的式I和II的结构要求的特定化合物的实例包括:
式I-i:2-均三甲苯基-4,5-二苯基-1H-咪唑,
式I-ii:2-(2,6-二氯苯基)-4-(2,5-二甲基苯基)-5-苯基-1H-咪唑,
式I-iii:2-(2-氯-6-氟苯基)-4-(2,5-二甲基苯基)-5-苯基-1H-咪唑,
式I-iv:2-(2,4-二甲氧基苯基)-4,5-二苯基-1H-咪唑,
式I-v:2-(2-乙氧基苯基)-4,5-二苯基-1H-咪唑,
式I-vi:4,5-二苯基-2-(2-(丙-2-炔-1-基氧基)苯基)-1H-咪唑,
式I-vii:5-(3-氯苯基)-2-(2,4-二氯苯基)-4-苯基-1H-咪唑,
式I-viii:4,5-二苯基-2-(2,3,4-三甲氧基苯基)-1H-咪唑,
式I-ix:2-(4-(甲硫基)苯基)-4,5-二-对甲苯基-1H-咪唑,
式I-x:(4-氟苯基)(4-(2-(3-氟苯基)-5-苯基-1H-咪唑-4-基)苯基)甲酮,
式II-i:N-烯丙基-3-苯基-1-(对甲苯基)-1H-吡唑-4-甲酰胺,
式II-ii:N-(2-甲基环己基)-1-苯基-3-(噻吩-2-基)-1H-吡唑-4-甲酰胺,
式II-iii:3-(2-氯苯基)-N-(2-乙氧基乙基)-1-甲基-1H-吡唑-4-甲酰胺,
式II-iv:3-(2-氯苯基)-1-甲基-N-(2-(四氢呋喃-2-基)乙基)-1H-吡唑-4-甲酰胺,和
式II-v:3-(2-氯苯基)-1-甲基-N-(四氢-2H-噻喃-4-基)-1H-吡唑-4-甲酰胺,
本文还提供了包含有效量的式I、式II的化合物或其混合物的组合物,用于施用于植物、种子、土壤或昆虫以防治害虫。本文还明确描述了使用含有有效量的此类化合物的组合物的方法。应该认识到,式I和/或式II的化合物的有效量可以根据组合物的施用方式而不同。例如,与将组合物直接施用于昆虫时相比,将组合物施用于植物可能需要不同的有效量。在另一个实例中,对于不同类型的昆虫,式I或式II化合物的有效量可能不同。此外,应该认识到,式I和/或式II化合物的有效量可代表足以杀死某种类型的害虫的量。然而,应该认识到,在一些替代实施方案中,例如,有效量可以代表足以驱除害虫远离目标区域和/或防止害虫再生的量。
可以有效量存在于本公开的组合物中的特定化合物、互变异构体或盐包括例如式I-i至I-x和II-i至II-v的化合物。
本公开的组合物可以选自多种制剂类型,包括但不限于可溶性浓缩物、悬浮浓缩物、油混溶性液体、超低容量液体、可乳化浓缩物、可分散浓缩物、微乳液、乳液(油包水和油包水)、油分散体、胶囊悬浮液和微囊化颗粒。其它实例包括干组合物,包括但不限于可喷撒粉末、可溶性粉剂、水溶性颗粒剂、可湿性粉剂、水分散性颗粒剂、可涂抹颗粒剂和种子处理剂。
本文所述的组合物可以包含本领域已知的任何佐剂、赋形剂或其它期望的组分。附加成分的非限制性实例包括表面活性剂、助表面活性剂、渗透促进剂、分散剂、润湿剂和共溶剂。
在一些实施方案中,本文所述的组合物可以进一步包含表面活性剂。合适的表面活性剂可以包括促进式I或式II的化合物在液相中分散的那些。可以针对与特定应用和化合物的相容性选择表面活性剂。合适的表面活性剂可选自阳离子表面活性剂、阴离子表面活性剂、两性离子表面活性剂和中性表面活性剂,并且每种类别的说明性实例对于本领域普通技术人员来说都是熟悉的。
在另外的实施方案中,本文所述的组合物可以进一步包含另外的共活性物质。共活性物质可以是例如杀昆虫剂、杀真菌剂、除草剂、杀线虫剂、生物防治剂、微生物或其任何混合物。下文提供了这些另外的共活性物质的合适实例。
杀昆虫剂和杀线虫剂的非限制性实例包括氨基甲酸酯、二酰胺、大环内酯、新烟碱、有机磷酸酯、苯基吡唑、除虫菊酯、多杀菌素、合成除虫菊酯、四氢酸以及四聚酸。例如,液态种子处理组合物可包含一种或多种以下的杀昆虫剂和杀线虫剂:阿维菌素、涕灭威、涕灭砜威、联苯菊酯、克百威、氯虫苯甲酰胺、可尼丁、氰虫酰胺、氟氯氰菊酯、三氟氯氰菊酯、氯氰菊酯、溴氰菊酯、呋虫胺、甲氨基阿维菌素、乙虫腈、克线磷、氟虫腈、氟虫双酰胺、噻唑磷、吡虫啉、双氢除虫菌素、高效氯氟氰菊酯、密灭汀、替噁扎芬(tioxazafen)、烯啶虫胺、草氨酰、氯菊酯、乙基多杀菌素、多杀霉素、季酮螨酯(spirodichlofen)、螺虫乙酯、七氟菊酯、噻虫啉、噻虫嗪、替噁扎芬以及硫双威。
适用的杀真菌剂的非限制性实例包括芳族烃、苯并咪唑、苯并噻二唑、羧酰胺、羧酸酰胺、吗啉、苯基酰胺、膦酸酯、醌外部抑制剂(例如嗜球果伞素(strobilurin))、噻唑烷、托布津(thiophanate)、噻吩羧酰胺和三唑。杀真菌剂的非限制性实例包括阿拉酸式苯-S-甲基(acibenzolar-S-methyl)、嘧菌酯(azoxystrobin)、苯霜灵(benalaxyl)、联苯吡菌胺(bixafen)、啶酰菌胺(boscalid)、多菌灵(carbendazim)、百菌清(chlorothalonil)、环丙唑醇(cyproconazole)、烯酰吗啉(dimethomorph)、氟环唑(epoxiconazole)、咯菌腈(fludioxonil)、氟吡菌酰胺(fluopyram)、氟唑菌酰胺(fluxapyroxad)、氟嘧菌酯(fluoxastrobin)、氟噻菌净(flutianil)、氟酰胺(flutolanil)、氟苯吡菌胺(fluxapyroxad)、三乙膦酸铝(fosetyl-Al)、种菌唑(ipconazole)、吡唑萘菌胺(isopyrazam)、醚菌酯(kresoxim-methyl)、精甲霜灵(mefenoxam)、甲霜灵(metalaxyl)、叶菌唑(metconazole)、腈菌唑(myclobutanil)、肟醚菌胺(orysastrobin)、戊苯吡菌胺(penflufen)、吡噻菌胺(penthiopyrad)、啶氧菌酯(picoxystrobin)、丙环唑(propiconazole)、丙硫菌唑(prothiconazole)、吡唑醚菌酯(pyraclostrobin)、氟唑环菌胺(sedaxane)、硅噻菌胺(silthiofam)、戊唑醇(tebuconazole)、噻苯咪唑(thiabendazole)、噻呋酰胺(thifluzamide)、托布津(thiophanate)、甲基立枯磷(tolclofos-methyl)、肟菌酯(trifloxystrobin)和灭菌唑(triticonazole)。
除草剂的非限制性实例包括ACC酶抑制剂、乙酰苯胺、AHAS抑制剂、类胡萝卜素生物合成抑制剂、EPSPS抑制剂、谷氨酰胺合成酶抑制剂、PPO抑制剂、PS II抑制剂以及合成生长素。除草剂的特定实例包括乙草胺、烯草酮、麦草畏、丙炔氟草胺、氟磺胺草醚、草甘膦、草胺磷、甲基磺草酮、喹禾灵、苯嘧磺草胺、磺草酮和2,4-D(2,4-二氯苯氧乙酸)。
另外的共活性物质还可包括诸如生物防治剂、微生物提取物、天然产物、植物生长活化剂或植物防御剂的物质。生物防治剂的非限制性实例包括细菌、真菌、有益线虫以及病毒。
在某些实施方案中,生物防治剂可包含以下属的细菌:放线菌属、农杆菌属、节细菌属、产碱杆菌属、金杆菌属、固氮菌属、芽孢杆菌属、拜叶林克氏菌属、慢生根瘤菌属、短芽孢杆菌属、伯克氏菌属、色杆菌属、梭菌属、棍状杆菌属、丛毛单胞菌属、棒状杆菌属、短杆菌属、肠杆菌属、黄杆菌属、葡糖杆菌属、噬氢菌属、克雷伯菌属、绿僵菌属、甲基杆菌属、类芽孢杆菌属、巴斯德氏芽菌属、发光杆菌属、叶杆菌属、假单胞菌属、根瘤菌、沙雷氏菌属、鞘氨醇杆菌属、寡养单胞菌属、链霉菌属、贪噬菌属和致病杆菌属。在某些实施方案中,细菌选自解淀粉芽孢杆菌、蜡样芽孢杆菌、坚强芽孢杆菌、地衣芽孢杆菌、短小芽孢杆菌、球形芽孢杆菌、枯草芽孢杆菌、苏云金杆菌、慢生型大豆根瘤菌血吸虫(japonicum)、津贺色杆菌(Chromobacterium subtsugae)、绿僵菌、拟斯扎瓦巴斯德氏芽菌(Pasteurianishizawae)、穿刺巴斯德氏芽菌属(Pasteuria penetrans)、巴氏杆菌(Pasteuriausage)、荧光假单胞菌和利迪链霉菌。
在某些实施方案中,生物防治剂可包含以下属的真菌:链格孢属、白粉寄生孢属、曲霉属、短梗霉属、白僵菌属、刺盘抱属、盾壳霉属、胶霉属、绿僵菌属、麝香霉属、拟青霉属、青霉属、木霉属、核瑚菌属、单格孢属、轮枝孢属。在另一个实施方案中,真菌是白僵菌、盾壳霉、绿粘帚菌、白粘帚菌、淡紫色拟青霉、比莱青霉、棘胞木霉、多抱木霉菌或绿木霉。
在某些实施方案中,生物防治剂可以包含超敏蛋白、大虎杖(Reynoutriasachalinensis)、茉莉酮酸酯、脂壳寡糖、水杨酸和/或异黄酮。在另一个实施方案中,生物防治剂可以包含坚强芽孢杆菌。
本文所述的化合物和组合物可以施用于种子、植物或植物的生长介质(例如,土壤),其中期望防治昆虫。化合物和组合物同样可以直接施用于昆虫用于类似的目的。例如,在各个实施方案中,本公开提供了防治害虫的方法,其中所述方法包括向植物、种子、土壤或昆虫施用包含有效量的本文所述化合物的组合物。
更具体地,在一些实施方案中,本文所述的方法可包括向植物、种子、土壤或昆虫施用包含式I的化合物、其互变异构体或其盐的组合物,其中式I中的变量如上所定义。在一些或其它实施方案中,本文所述的方法可包括向植物、种子、土壤或昆虫施用包含式II的化合物或其盐的组合物,其中式II中的变量如上所定义。
认为组合物施用于植物、种子、土壤和/或昆虫的技术不被特别限制。具体的技术可以根据组合物施用的靶标来选择。合适的技术可以包括例如在施用于植物或昆虫的情况下铺展固体制剂或喷洒组合物的液体制剂。例如,在施用于种子的情况下,可以将组合物与料斗中的多个种子混合,或者可以将液体制剂喷洒在多个种子上。
在一些实施方案中,组合物可以施用于种子。在其它实施方案中,组合物可以施用于植物。在更特定的实施方案中,组合物可以施用于植物的叶子或植物根区周围的土壤。在其它实施方案中,组合物可以直接施用于昆虫。例如,以给定方式进行的施用的选择可以由昆虫主要是表层昆虫还是亚表层昆虫来决定。
根据本文所述的方法可以被保护免受害虫侵害的植物的非限制性实例包括单子叶植物如玉米、小麦、大麦、黑麦、甘蔗、稻、高粱、燕麦;双子叶植物如棉花、甜菜、花生、马铃薯、甘薯、山药向日葵、大豆、苜蓿、亚麻、卡诺拉油菜、葡萄、烟草;蔬菜包括茄科蔬菜如茄子、番茄、青椒和胡椒;葫芦科蔬菜如黄瓜、南瓜、西葫芦、西瓜、甜瓜和南瓜;十字花科蔬菜如萝卜(radish)、萝卜(turnip)、辣根、大白菜、卷心菜、芥菜、西兰花和菜花;菊科蔬菜如朝鲜蓟和生菜;百合科蔬菜如韭葱、洋葱、大蒜和芦笋;伞形科蔬菜如胡萝卜、欧芹、芹菜和欧洲防风草;藜科蔬菜如菠菜和牛皮菜;唇形科蔬菜如薄荷和罗勒;花卉如矮牵牛、牵牛花、康乃馨、菊花和玫瑰;叶子植物;果树如梨果(例如,苹果,梨和日本梨)、核果(例如,桃、李子、油桃、樱桃、杏和西梅)、柑橘(例如,橙、柠檬、酸橙和葡萄柚)、坚果(例如,栗子、山核桃、核桃、榛子、杏仁、开心果、腰果和夏威夷果)、浆果如蓝莓、蔓越莓、黑莓、草莓和覆盆子;柿子;橄榄;枇杷;香蕉;咖啡;棕榈;可可;其它树木如茶树、桑树、花树和风景树(例如,灰桦木(ash,birch)、山茱萸、桉树、银杏、紫丁香、枫树、橡树、白杨、福尔摩沙甜树胶、美国梧桐、冷杉、铁杉、杜松、松树、云杉和红豆杉);和草皮。
可通过本文所述方法防治的害虫的非限制性实例包括鞘翅目、双翅目、半翅目和鳞翅目的成员。
鞘翅目成员的非限制性实例包括Acalymma、三齿豆象属(Acanthoscelides)、喙丽金龟属(Adoretus)、杨树萤叶甲(Agelastica)、叩甲属(Agriotes)、粉虫属(Alphitobius)、双绺鳃金龟科(Amphimallon)、窃蠹属(Anobium)、星天牛属(Anoplophora)、花象属(Anthonomus)、圆皮蠹属(Anthrenus)、阿皮翁(Apion)、甘蔗金龟属(Apogonia)、谷类蚜虫(Atomaria)、毛皮蠹属(Attagenus)、多型豆象(属Bruchidius)、豆象属(Bruchus)、龟甲属(Cassida)、叶甲属(Cerotoma)、象甲属(Ceutorrhynchus)、凹胫跳甲属(Chaetocnema)、方喙象属(Cleonus)、宽胸叩头虫属(Conoderus)、根颈象属(Cosmopolites)、肋翅鳃角金龟属(Costelytra)、叩甲属(Ctenicera)、象虫属(Curculio)、隐喙象属(Cryptorhynchus)、细枝象属(Cylindrocopturus)、皮蠹属(Dermestes)、叶甲属(Diabrotica)、蛀野螟属(Dichocrocis)、挤螬(Diloboderus)、食植瓢虫属(Epilachna)、毛跳甲属(Epitrix)、烟草钻孔虫(Faustinus)、裸蛛甲属(Gibbium)、菜心野螟属(Hellula)、异爪犀金龟属(Heteronychus)、寡节鲍金龟属(Heteronyx)、褐翅椿象(Hylamorpha)、家天牛属(Hylotrupes)、细叉叶象属(Hypera)、咪小蠹属(Hypothenemus)、甘蔗大褐齿爪鲍金龟(Lachnosterna)、细颈金花虫属(Lema)、叶甲属(Leptinotarsa)、银潜蛾属(Leucoptera)、稻水象属(Lissorhoptrus)、筒喙象属(Lixus)、萤叶甲属(Luperodes)、粉蠹属(Lyctus)、美洲叶甲属(Megascelis)、梳爪叩头虫属(Melanotus)、菜花露尾甲属(Meligethes)、鳃金龟属(Melolontha)、天牛属(Migdolus)、墨天牛属(Monochanus)、缘象属(Naupactus)、褐蛛甲属(Niptus)、蛀犀金龟属(Oryctes)、锯谷盗属(Oryzaephilus)、(Oryzaphagus)、耳象属(Otiorrhynchus)、小青花金龟(Oxycetonia)、条背金花虫属(Phaedon)、鳃角金龟属(Phyllophaga)、条跳甲属(Phyllotreta)、弧丽金龟属(Popillia)、象甲属(Premnotrypes)、尖帽胸长蠹属(Prostephanus)、蚤跳甲属(Psylliodes)、蛛甲属(Ptinus)、暗色瓢虫属(Rhizobius)、谷蠹属(Rhizopertha)、谷象属(Sitophilus)、尖隐喙象属(Sphenophorus)、药材甲属(Stegobium)、茎干象属种(Sternechus)、(Symphyletes)、纤毛象属(Tanymecus)、粉甲虫属(Tenebrio)、拟谷盗属(Tribolium)、斑皮蠹属(Trogoderma)、籽象属(Tychius)、脊虎天牛属(Xylotrechus)和距步甲属(Zabrus)。
双翅目成员的非限制性实例包括伊蚊属(Aedes)、潜蝇属(Agromyza)、实蝇属(Anastrepha)、按蚊属(Anopheles)、花椒瘿蚊(Asphondylia)、果实蝇属(Bactrocera)、毛蚊属(Bibio)、丽蝇属(Calliphora)、蜡实蝇属(Ceratitis)、摇蚊属(Chironomus)、金蝇属(Chrysomyia)、斑虻属(CHrysops)、锥蝇属(Cochliomyia)、康瘿蚊属(Contarinia)、瘤蝇属(Cordylobia)、库蚊属(Culex)、库蠓属(Culicoides)、脉毛蚊属(Culiseta)、黄蝇属(Cuterebra)、寡毛实蝇属(Dacus)、叶癭蚊属(Dasyneura)、地种蝇属(Delia)、皮蝇属(Dermatobia)、果蝇属(Drosophila)、稻象属(Echinocnemus)、厕蝇属(Fannia)、胃蝇属(Gasterophilus)、舌蝇属(Glossina)、麻虻属(Haematopota)、毛眼水蝇属(Hydrellia)、黑蝇属(Hylemyia)、虱蝇属((Hyppobosca)、皮蝇属(Hypoderma)、斑潜蝇属(Liriomyza)、绿蝇属(Lucilia)、罗蛉属(Lutzomia)、曼蝇属(Mansonia)、蝇属(Musca)、绿蝽属(Nezara)、狂蝇属(Oestrus)、麦杆蝇(Oscinella)、泉蝇属(Pegomyia)、白蛉属(Phlebotomus)、草种蝇属(Phorbia)、伏蝇属(Phormia)、(Prodiplosis)、茎潜蝇属(Psila)、绕实蝇属(Rhagoletis)、嘛蝇属(Sarcophaga)、蚋属(Simulium)、蝇属(Stomoxys)、虻属(Tabanus)、螗蜩属(Tannia)、根斑蝇属(Tetanops)和大蚊属(Tipula)。
半翅目(亚目异翅目)的非限制性实例包括南瓜缘蝽(Anasa tristis)、拟丽蝽属种(Antestiopsis spp.)、Boisea spp.、土长蝽属种(Blissus spp.)、俊盲蝽属种(Calocoris spp.)、绿微刺盲蝽(Campylomma livida)、异背长蝽属种(Cavelerius spp.)、臭虫属种(Cimex spp.)、温带臭虫(Cimex lectularius)、热带臭虫(Cimex hemipterus)、白辧麦寄绳属种(Collaria spp.)、绿盲蝽(Creontiades dilutus)、胡椒缘蝽(Dasynuspiperis)、Dichelops furcatus、厚氏长棒网蝽(Diconocoris hewetti)、棉红蝽属种(Dysdercus spp.)、美洲蝽属种(Euschistus spp.)、扁盾蝽属种(Eurygaster spp.),茶角盲蝽属种(Heliopeltis spp.)、具凹巨股长蝽(Horcias nobilellus)、稻缘蝽属种(Leptocorisa spp.)、叶足缘蝽(Leptoglossus phyllopus)、草盲蝽属种(Lygus spp.)、鹿黑长蝽(Macropes excavatus)、盲蝽科(Miridae)、黑摩盲蝽(Monalonion atratum)、绿蝽属种(Nezara spp.)、稻蝽属种(Oebalus spp.)、蝽科动物(Pentomidae)、方背皮蝽(Piesmaquadrata)、璧蝽属种(Piezodorus spp.)、杂盲蝽属种(Psallus spp.)、Pseudacystapersea,红猎蝽属种(Rhodnius spp.)、可可褐盲蝽(Sahlbergella singularis)、齿栗叶盾蝽(Scaptocoris castanea)、黑蝽属种(Scotinophora spp.)、梨冠网蝽(Stephanitisnashi)、Tibraca spp.、锥猎蝽属种((Triatoma spp)。
同翅目成员的非限制性实例包括无网长管虫牙属种(Acyrthosiponspp.)、Acrogonia spp.、Aeneolamia spp.、隆脉木虱属种(Agonoscena spp.)、粉虱属种(Aleurodes spp.)、甘蔗穴粉虱(Aleurolobus barodensis)、颈粉虱属种(Aleurothrixusspp.)、芒果叶蝉属种(Amrasca spp.)、飞廉短尾蚜(Anuraphis cardui)、肾圆盾介壳虫属种(Aonidiella spp.)、梨矮蚜(Aphanostigma piri)、蚜虫属种(Aphis spp.)、葡萄叶蝉(Arboridia apicalis)、小圆盾蚁属种(Aspidiella spp.)、薄圆盾介壳虫属种(Aspidiotus spp.)、Atanus spp.、茄沟无网蚜(Aulacorthum solani)、小粉虱属(Bemisiaspp.)、李短尾蚜(Brachycaudus helichrysii)、小管蚜属种(Brachycolus spp.)、甘蓝蚜(Brevicoryne brassicae)、小褐稻虱(Calligypona marginata)、丽黄头大叶蝉(Carneocephala fulgida)、甘庶粉角蚜(Ceratovacuna lanigera)、沫蝉科(Cercopidae)、蜡蚧属种(Ceroplastes spp.)、草莓钉蚜(Chaetosiphon fragaefolii)、庶黄雪盾蚁(Chionaspis tegalensis)、荼绿叶蝉(Chlorita onukii)、核桃黑斑蚜(Chromaphisjuglandicola)、褐圆介壳虫(Chrysomphalus ficus)、玉米叶蝉(Cicadulina mbila)、葛根贝盾蚧(Coccomytilus halli)、软蚧属种(Coccus spp.)、隐瘤蚜(Cryptomyzus ribis)、叶蝉属种(Dalbulus spp.)、裸粉虱属种(Dialeurodes spp.)、桔木虱属种(Diaphorinaspp.)、白背盾蚧属种(Diaspis spp.)、草履介壳虫属种(Drosicha spp.)、西圆尾蚜属种(Dysaphis spp.)、灰粉蚧属种(Dysmicoccus spp.)、小绿叶蝉属种(Empoasca spp.)、绵蚜属种(Eriosoma spp.)、斑叶蝉属种(Erythroneura spp.)、钝鼻叶蝉(Euscelisbilobatus)、腺刺粉蚧属(Ferrisia spp.)、咖啡地粉蚧(Geococcus coffeae)、蔗蝗属种(Hieroglyphus spp.)、琉璃叶蝉(Homalodisca coagulata)、桃大尾蚜(Hyalopterusarundinis)、吹绵蚧属种(Icerya spp.)、片角叶蝉属种(Idiocerus spp.)、扁喙叶蝉属种(Idioscopus spp.)、灰飞虱(Laodelphax striatellus)、蜡蚧属(Lecanium spp.)、牡蛎蚧属种(Lepidosaphes spp.)、萝卜蚜(Lipaphis erysimi)、长管蚜属(Macrosiphum spp.)、沫蝶属种(Mahanarva spp.)、高粱蚜(Melanaphis sacchari)、角蝉属种(Metcalfiellaspp.)、麦无网长管蚜(Metopolophium dirhodum)、黑缘平翅斑蚜(Monellia costalis)、山核桃平翅斑蚜(Monelliopsis pecanis)、瘤蚜属种(Myzus spp.)、苣衲长管蚜(Nasonoviaribisnigri)、黑尾叶蝉属种(Nephotettix spp.)、褐飞虱(Nilaparvata lugens)、大叶蝉属种(Oncometopia spp.)、普来隆旌蚧(Orthezia praelonga)、杨梅粉虱(Parabemisiamyricae)、木虱属种(Paratrioza spp.)、片盾蚧属种(Parlatoria spp.)、瘿绵蚜属属种(Pemphigus spp.)、玉米蜡蝉(Peregrinus maidis)、绵粉蚧属属种(Phenacoccus spp.)、杨平翅绵蚜(Phloeomyzus passerinii)、忽布疣蚜(Phorodon humuli)、葡萄根瘤蚜(Phylloxera spp.)、苏铁褐点并盾蚧(Pinnaspis aspidistrae)、动性球菌属种(Planococcus spp.)、梨形原绵腊蚧(Protopulvinaria pyriformis)、桑白盾蚧(Pseudaulacaspis pentagona)、粉蚧属种(Pseudococcus spp.)、木虱属种(Psyllaspp.)、金小蜂属种(Pteromalus spp.)、蜡蝉属种(Pyrilla spp.)、齿盾蚧属种(Quadraspidiotus spp.)、Quesada gigas、平刺粉蚧属种(Rastrococcus spp.)、缢管蚜属种(Rhopalosiphum spp.)、黑盔蚧属种(Saissetia spp.)、葡萄带叶蝉(Scaphoidestitanus)、麦二叉蚜(Schizaphis graminum)、刺盾蚧(Selenaspidus articulatus)、长唇基飞虱属种(Sogata spp.)、白背飞虱(Sogatella furcifera)、稻飞虱属种(Sogatodesspp.)、三角蝶(Stictocephala festina)、Tenalaphara malayensis、美洲山核桃长斑蚜(Tinocallis caryaefoliae)、广胸沫蝉属种(Tomaspis spp.)、声蚜属种(Toxopteraspp.)、粉虱属种(Trialeurodes spp.)、尖翅木虱属种(Trioza spp.)、小叶蝉属种(Typhlocyba spp.)、矢尖盾蚧属种(Unaspis spp.)、葡萄根瘤蚜(Viteus vitifolii)、么叶蝉属种(Zygina spp.)。
鳞翅目的成员的非限制性实例包括桑剑纹夜蛾(Acronicta major)、褐带卷蛾属(Adoxophyes)、白斑烦夜蛾(Aedia leucomelas)、地夜蛾属(Agrotis)、波纹夜蛾属(Alabama)、脐橙螟蛾(Amyelois transitclla)、条麦蛾属(Anarsia)、(Anticarsia)、干煞夜蛾属(Argyroploce)、甘蓝夜蛾(Barathra brassicae)、禾弄蝶(Borbo cinnara)、棉潜蛾(Bucculatrix thurberiella)、松尺蠖(Bupalus piniarius)、蛀褐夜蛾属(Busseola)、卷夜蛾属(Cacoecia)、茶细蛾(Caloptilia theivora)、烟卷蛾(Capua reticulana)、苹果蠹蛾(Carpocapsa pomonella)、桃蛀果蛾(Carposina niponensis)、Chematobia brumata、禾草螟属(Chilo)、色卷蛾属(Choristoneura)、葡萄果蠹蛾(Clysia ambiguella)、纵卷叶野螟属(Cnaphalocerus)、云卷蛾属(Cnephasia)、细蛾属(Conopomorpha)、球颈象属(Conotrachelus)、Copitarsia、小卷蛾属(Cydia)、Dalaca noctuides、绢野螟属(Diaphania)、小蔗螟(Diatraea saccharalis)、钻夜蛾属(Earias)、Ecdytolophaaurantium、南美玉米苗斑螟(Elasmopalpus lignosellus)、甘薯杆螟(Eldanasaccharina)、粉斑螟属(Ephestia)、叶小卷蛾属(Epinotia)、苹果褐卷蛾(Epiphyaspostvittana)、荚斑螟属(Etiella)、Eulia、葡萄与苹果卷叶蛾(Eupoecilia ambiguella)、黄毒蛾属(Euproctis)、切夜蛾属(Euxoa)、脏切叶蛾属(Feltia)、大蜡螟(Galleriamellonella)、细蛾属(Gracillaria)、小食心虫属(Grapholitha)、蚀叶野螟属(Hedylepta)、铃夜蛾属(Helicoverpa)、实夜蛾属(Heliothis)、褐织蛾(Hofmannophilapseudospretella)、斑螟属(Homoeosoma)、长卷蛾属(Homona)、苹果巢蛾(Hyponomeutapadella)、柿蒂虫(Kakivoria flavofasciata)、夜蛾属(Laphygma)、梨小食心虫(Laspeyresia molesta)、黄斑螟(Leucinodes orbonalis)、银潜蛾属(Leucoptera)、潜叶细蛾属(Lithocolletis)、绿果冬夜蛾(Lithophane antennata)、花翅小蛾属(Lobesia)、豆白隆切根虫(Loxagrotis albicosta)、毒蛾属(Lymantria)、潜蛾属(Lyonetia)、幕毛虫(Malacosoma neustria)、豆荚野螟(Maruca testulalis)、甘蓝夜蛾(Mamestrabrassicae)、毛胫夜蛾属(Mocis)、粘虫(Mythimna separata)、水螟属(Nymphula)、(Oiketicus)、麦杆夜蛾属(Oria)、瘤丛螟属(Orthaga)、秆野螟属(Ostrinia)、水稻负泥虫(Oulema oryzae)、小眼夜蛾(Panolis flammea)、稻弄蝶属(Parnara)、红铃麦蛾属(Pectinophora)、潜叶蛾属(Perileucoptera)、茄麦蛾属(Phthorimaea)、柑桔叶潜蛾(Phyllocnistis citrella)、小潜细蛾属(Phyllonorycter)、粉蝶属(Pieris)、荷兰石竹小卷蛾(Platynota stultana)、印度谷螟(Plodia interpunctella)、金翅夜蛾属(Plusia)、小菜蛾(Plutella xylostella)、小白巢蛾属(Prays)、斜纹夜蛾属(Prodenia)、烟草天蛾(Protoparce)、黏虫属(Pseudaletia)、大豆尺夜蛾(Pseudoplusia includens)、欧洲玉蜀黍螟(Pyrausta nubilalis)、尺蠖(Rachiplusia nu)、禾螟属(Schoenobius)、白禾螟属(Scirpophaga)、黄地老虎(Scotia segetum)、蛀茎夜蛾属(Sesamia)、长须卷蛾属(Sparganothis)、灰翅夜蛾属(Spodoptera)、展足蛾属(Stathmopoda)、花生麦蛾属(Stomopteryx subsecivella)、兴透翅蛾属(Synanthedon)、马铃墓块茎蛾属(Teciasolanivora)、Thermesia gemmatalis、袋谷蛾(Tinea pellionella)、幕谷蛾(Tineolabisselliella)、卷夜蛾(Tortrix)、毛毡衣蛾(Trichophaga tapetzella)、粉夜蛾属(Trichoplusia)、番茄斑潜蝇(Tuta absoluta)和灰蝶属(Virachola)。
在更特定的实施方案中,可以通过实施本文的公开内容来防治的示例性害虫包括例如小菜蛾、秋夜蛾、大豆夜蛾、西方玉米根虫,西方牧草盲蝽和埃及伊蚊。
根据本文公开内容可被保护免受害虫侵害的植物的非限制性实例包括作物植物。根据本文公开内容可被保护的示例性作物植物包括例如玉米、棉花、大豆、谷类、花生、向日葵、干豆类、豌豆、豆荚蔬菜、甘蔗、苜蓿和卡诺拉油菜。观赏植物可以用类似的方式进行保护。
在一些实施方案中,本公开涉及已用本文所述的组合物处理的种子,所述组合物包含式I的化合物、互变异构体或盐和/或式II的化合物或盐。式I和/或式II的化合物与得到的经处理的种子相关联。经处理的种子在种植时可促进式I和/或式II的化合物向植物周围的根区分布。在一些实施方案中,可以利用种子处理(例如固体基质引发、吸入、涂布和喷雾)将组合物施用于种子。经处理的种子可以是本文所述的任何植物物种的种子。在一些实施方案中,种子可以用本文所述的组合物处理,包括配制,在种子处理池中混合,或者通过外涂一种或多种另外的活性成分在种子上结合。活性成分可以是例如杀昆虫剂、杀真菌剂、除草剂、杀线虫剂、生物防治剂或微生物。在一些实施方案中,种子也可以是转基因种子。
本文公开的实施方案包括:
实施方案A.一种防治害虫的方法。该方法包括:向植物、种子、土壤或昆虫施用包含式I的化合物、其互变异构体或其盐的组合物
其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基;其中R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基;其中R1-R5中至少一者不是氢;其中R6和R7独立地选自氢、卤素和烷基;其中R8选自氢、烷基和任选取代的酰基苯基;并且其中R9选自氢和烷基。
实施方案B.一种防治害虫的方法。该方法包括:向植物、种子、土壤或昆虫施用包含式II的化合物或其盐的组合物
其中R10选自任选取代的芳基和任选取代的烷基;其中R11选自任选取代的芳基和任选取代的杂芳基;其中R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基;并且其中Z是C1-C6烷基或键。
实施方案C.杀虫处理组合物。处理组合物包含:式I的化合物、其互变异构体或其盐
其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基;其中R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基;其中R1-R5中至少一者不是氢;其中R6和R7独立地选自氢、卤素和烷基;其中R8选自氢、烷基和任选取代的酰基苯基;并且其中R9选自氢和烷基。
实施方案D.经处理的种子。经处理的种子包含式I的化合物、其互变异构体或其盐。
实施方案E.杀虫处理组合物。处理组合物包含:式II的化合物或其盐
其中R10选自任选取代的芳基和任选取代的烷基;其中R11选自任选取代的芳基和任选取代的杂芳基;其中R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基;并且其中Z是C1-C6烷基或键。
实施方案F.经处理的种子。经处理的种子包含式II的化合物或其盐。
实施方案A-F中的每一个可具有任意组合的下列附加要素中的一个或多个。
要素1:其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基和炔氧基。
要素2:其中将有效量的选自2-均三甲苯基-4,5-二苯基-1H-咪唑、2-(2,6-二氯苯基)-4-(2,5-二甲基苯基)-5-苯基-1H咪唑、2-(2-氯-6-氟苯基)-4-(2,5-二甲基苯基)-5-苯基-1H-咪唑、2-(2,4-二甲氧基苯基)-4,5-二苯基-1H-咪唑、2-(2-乙氧基苯基)-4,5-二苯基-1H咪唑、4,5-二苯基-2-(2-(丙-2-炔-1-基氧基)苯基)-1-H-咪唑、5-(3-氯苯基)-2-(2,4-二氯苯基)-4-苯基-1H咪唑、4,5-二苯基-2-(2,3,4-三甲氧基苯基)-1H-咪唑、2-(4-(甲硫基)苯基)-4,5-二-对甲苯基-1H-咪唑、(4-氟苯基)(4-(2-(3-氟苯基)-5-苯基-1H-咪唑-4-基)苯基)甲酮的化合物、其互变异构体及其盐施用于植物、种子、土壤或昆虫。
要素3:其中将组合物施用于种子。
要素4:其中将组合物施用于植物。
要素5:其中将组合物施加于植物的叶子。
要素6:其中将组合物施加于植物根区周围的土壤。
要素7:其中植物是选自玉米、棉花、大豆、谷类、花生、向日葵、干豆类、豌豆、豆荚蔬菜、甘蔗、苜蓿和卡诺拉油菜的作物植物。
要素8:其中害虫是选自鞘翅目、双翅目、半翅目和鳞翅目的成员。
要素9:其中害虫是以下属的成员:伊蚊属、叶甲属、草盲蝽属、菜蛾属、尺夜蛾属和灰翅夜蛾属。
要素10:其中害虫选自小菜蛾、秋夜蛾、大豆夜蛾、西方玉米根虫和埃及伊蚊。
要素11:其中处理组合物还包含表面活性剂。
要素12:其中处理组合物还包含杀真菌剂、杀昆虫剂、杀线虫剂、除草剂、微生物或其混合物。
要素13:其中R10选自苯基和甲苯基,并且R11选自苯基、噻吩基和氯苯基。
要素14:其中R12选自烯丙基、2-甲基环己基、乙氧基、四氢呋喃-2-基、四氢-2H-噻喃-4-基,并且Z是C1-C3烷基或键。
要素15:其中将有效量的选自N-烯丙基-3-苯基-1-(对甲苯基)-1H-吡唑-4-甲酰胺、N-(2-甲基环己基)-1-苯基-3-(噻吩-2-基)-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-N-(2-(乙氧基乙基)-1-甲基-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-1-甲基-N-(2-(四氢呋喃-2-基)乙基)-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-1-甲基-N-(四氢-2H-噻喃-4-基)-1H-吡唑-4-甲酰胺的化合物及其盐施用于植物、种子、土壤或昆虫。
已详细描述本公开,将显而易见的是,在不脱离权利要求的范围的情况下,修改和变化是可能的。以下实施例仅被认为是说明性的,并不意图限制本发明的范围。
实施例
通常,式I和II的化合物可以使用本领域普通技术人员已知的方法的扩展来制备。
实施例1:式I的化合物的合成。式I的化合物可以如以下方案1中示出的示例性合成路线所示制备。具有不同组取代的5-溴咪唑3可以通过1,1-二溴烯烃1与相应的脒2的铜催化环胺化反应来制备。三取代的咪唑5可以由相应的5-溴咪唑3与适当的芳基硼酸4在方案1中描述的条件下进行Suzuki-Miyaura交叉偶联来制备。脱保护后,得到式I的化合物。
方案1:制备式I的化合物的合成方案
此外,式I的某些化合物还可以如以下方案2中大体阐述的那样制备。2-芳基-4,5-二溴咪唑8可以通过使芳醛6与1,2-乙二胺反应然后用N-溴代琥珀酰亚胺溴化中间体7来制备。如方案2所述,式I的化合物可以由4,5-二溴咪唑8通过与芳基硼酸9进行Suzuki-Miyaura交叉偶联来制备。如方案2所示,选择芳基硼酸9被使得具有对称取代的式I的化合物形成(即,R8=R9且R6=R7=H)。式I的不对称化合物可以通过使用差异取代的芳基硼酸9(即,一种具有R6、R7和R8全取代的芳基硼酸和一个具有R9取代的芳基硼酸)来制备。当采用不同的芳基硼酸9时,可能会产生由芳基硼酸9和4,5-二溴咪唑8的统计反应生成的差异取代的区域异构体,其可能需要进一步分离。
方案2:制备式I的化合物的合成方案
实施例2:式II的化合物的合成。式II的化合物可以如方案3中的示例性反应所示制备。中间体吡唑甲醛14可以通过芳基腙12与Vilsmeier-Haack试剂(DMF/POCl3)的反应来制备。在0℃、氨基磺酸清除剂存在下,用NaOCl2对中间体吡唑甲醛14进行的氧化提供相应的酸15。芳基腙12由相应的苯乙酮、二苯甲酮或酰基杂芳族衍生物10和肼11在乙酸存在下于乙醇中制备。式II的化合物可以由相应的酸15和胺16在碱(例如,三乙胺)存在下使用标准偶联试剂如CDI或EDCI/HOBt来制备。
方案3:制备式II的化合物的合成方案
实施例3:昆虫饲养测定。为了评估对昆虫物种的防治,试验装置由填充了物种特异性的人工饵料的96孔生物测定板构成。将化合物溶解于DMSO中并作为饵料覆盖物添加至指定浓度,并在侵染前干燥/维持过夜。一经干燥,生物测定板每孔用单个新生幼虫(草盲蝽属若虫)侵染。然后将生物测定板在27℃且相对湿度为50%的培养箱中保持6天。然后根据昆虫的死亡率和发育迟缓来视觉评估样本响应。对显示高于未处理的对照的任何水平的发育迟缓和/或死亡率的样本给予“+”得分。对显示无活性的样本给予“-”得分。西方玉米根虫数据代表三次重复的汇总。所有其它昆虫物种的数据代表两次重复的汇总。汇总结果提供于下表中。
表1A:昆虫饲养测定-西方玉米根虫(WCR)
表1B:昆虫饲养测定-小菜蛾(DBM)
表1C:昆虫饲养测定-埃及伊蚊(YFM)
实施例4:昆虫饲养测定。在该实施例中,为了评估对昆虫物种的防治,试验装置由填充了物种特异性的人工饵料的96孔生物测定板构成。将化合物溶解于DMSO中并作为饵料覆盖物添加至指定浓度,并在侵染前干燥/维持过夜。一经干燥,生物测定板每孔用单个新生幼虫(草盲蝽属若虫)侵染。将生物测定板在27℃且相对湿度为50%的培养箱中保持6天。对每孔进行侵染和污染评估。受污染或未感染的孔不纳入发育迟缓和死亡率评估。基于8孔列内存活昆虫的相对大小报告发育迟缓得分,跨越3列重复取平均值。未经处理的对照昆虫被用作参考。死亡率百分比确定为未能从化合物处理存活下来的昆虫除以8孔列内的总昆虫的百分数并跨越3列重复取平均值。在这些测定条件下,+”代表与未处理的对照相比死亡率或发育迟缓显著不同,“-”代表与未处理的对照相比死亡率或发育迟缓无显著差异。
表2A:昆虫饲养测定-小菜蛾(DBM)
表2B:昆虫饲养测定-秋夜蛾(FAW)
表2C:昆虫饲养试验-大豆夜蛾(SL)
表2D:昆虫饲养测定-西方玉米根虫(WCR)
表2E:昆虫饲养测定-西方牧草盲蝽
表2F:昆虫饲养测定-埃及伊蚊(YFM)
在介绍本发明或其优选实施方案的要素时,冠词“一个/一种(a,an)”和“所述(the,said)”意指存在一个或多个要素。术语“包括”、“包含”以及“具有”旨在是包括性的,并且意指除所列出的要素之外可存在另外的要素。
鉴于以上,将明白的是:实现了本发明的若干目标,并且获得其它有利结果。
因为在不背离本发明范围的情况下,可在上述产品和方法中做出各种改变,所以以上说明中包含的所有内容均应理解为是说明性的并且不具有限制意义。
Claims (20)
1.一种防治害虫的方法,所述方法包括:
向植物、种子、土壤或昆虫施用包含式I的化合物、其互变异构体或其盐的组合物
其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基;
其中R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基;
其中R1-R5中至少一者不是氢;
其中R6和R7独立地选自氢、卤素和烷基;
其中R8选自氢、烷基和任选取代的酰基苯基;并且
其中R9选自氢和烷基。
2.如权利要求1所述的方法,其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基和炔氧基。
3.如权利要求1所述的方法,其中将有效量的选自2-均三甲苯基-4,5-二苯基-1H-咪唑、2-(2,6-二氯苯基)-4-(2,5-二甲基苯基)-5-苯基-1H-咪唑、2-(2-氯-6-氟苯基)-4-(2,5-二甲基苯基)-5-苯基-1H-咪唑、2-(2,4-二甲氧基苯基)-4,5-二苯基-1H-咪唑、2-(2-乙氧基苯基)-4,5-二苯基-1H-咪唑、4,5-二苯基-2-(2-(丙-2-炔-1-基氧基)苯基)-1-H-咪唑、5-(3-氯苯基)-2-(2,4-二氯苯基)-4-苯基-1H-咪唑、4,5-二苯基-2-(2,3,4-三甲氧基苯基)-1H-咪唑、2-(4-(甲硫基)苯基)-4,5-二-对甲苯基-1H-咪唑、(4-氟苯基)(4-(2-(3-氟苯基)-5-苯基-1H-咪唑-4-基)苯基)甲酮的化合物、其互变异构体及其盐施用于植物、种子、土壤或昆虫。
4.如权利要求1-3中任一项所述的方法,其中将所述组合物施用于种子。
5.如权利要求1至5中任一项所述的方法,其中所述害虫选自小菜蛾、秋夜蛾、大豆夜蛾、西方玉米根虫、西方牧草盲蝽和埃及伊蚊。
6.根据权利要求4所述的方法制备的经处理的种子,所述经处理的种子包含式I的化合物、其互变异构体或其盐。
7.一种处理组合物,其包含式I的化合物、其互变异构体或其盐
其中R1、R2和R3独立地选自氢、卤素、烷基、烷氧基、硫代烷基、烯氧基、炔氧基、卤代烷基和卤代烷氧基;
其中R4和R5独立地选自氢、卤素、烷基、烷氧基、烯氧基和炔氧基;
其中R1-R5中至少一者不是氢;
其中R6和R7独立地选自氢、卤素和烷基;
其中R8选自氢、烷基和任选取代的酰基苯基;并且
并且其中R9选自氢和烷基。
8.如权利要求7所述的处理组合物,其还包含表面活性剂。
9.如权利要求7或权利要求8所述的处理组合物,其进一步包含:
杀真菌剂、杀昆虫剂、杀线虫剂、除草剂、微生物或其混合物。
10.一种防治害虫的方法,所述方法包括:
向植物、种子、土壤或昆虫施用包含式II的化合物或其盐的组合物
其中R10选自任选取代的芳基和任选取代的烷基;
其中R11选自任选取代的芳基和任选取代的杂芳基;
其中R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基;并且
其中Z是C1-C6烷基或键。
11.如权利要求10所述的方法,其中R10选自苯基和甲苯基,并且R11选自苯基、噻吩基和氯苯基。
12.如权利要求10或权利要求11所述的方法,其中R12选自烯丙基、2-甲基环己基、乙氧基、四氢呋喃-2-基、四氢-2H-噻喃-4-基,并且Z是C1-C3烷基或键。
13.如权利要求10所述的方法,其中将有效量的选自N-烯丙基-3-苯基-1-(对甲苯基)-1H-吡唑-4-甲酰胺、N-(2-甲基环己基)-1-苯基-3-(噻吩-2-基)-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-N-(2-乙氧基乙基)-1-甲基-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-1-甲基-N-(2-(四氢呋喃-2-基)乙基)-1H-吡唑-4-甲酰胺、3-(2-氯苯基)-1-甲基-N-(四氢-2H-噻喃-4-基)-1H-吡唑-4-甲酰胺的化合物及其盐施用于植物、种子、土壤或昆虫。
14.如权利要求10-13中任一项所述的方法,其中将所述组合物施用于种子。
15.如权利要求10-13中任一项所述的方法,其中将所述组合物施用于植物。
16.如权利要求10-15中任一项所述的方法,其中所述害虫选自小菜蛾、秋夜蛾、大豆夜蛾、西方玉米根虫、西方牧草盲蝽和埃及伊蚊。
17.根据权利要求14的方法制备的经处理的种子,所述经处理的种子包含式II的化合物或其盐。
18.一种处理组合物,其包含式II的化合物或其盐
其中R10选自任选取代的芳基和任选取代的烷基;
其中R11选自任选取代的芳基和任选取代的杂芳基;
其中R12选自任选取代的烷基、任选取代的烯基、任选取代的炔基、任选取代的烷氧基、任选取代的杂环烷基和任选取代的完全饱和的环烷基;并且
其中Z是C1-C6烷基或键。
19.如权利要求18所述的处理组合物,其还包含表面活性剂。
20.如权利要求18或权利要求19所述的处理组合物,其进一步包含:
杀真菌剂、杀昆虫剂、杀线虫剂、除草剂、微生物或其混合物。
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US20210030001A1 (en) | 2021-02-04 |
CA3002451A1 (en) | 2017-05-26 |
BR112018009906A2 (pt) | 2018-11-13 |
WO2017087218A1 (en) | 2017-05-26 |
AR106735A1 (es) | 2018-02-14 |
EP3377486A4 (en) | 2019-09-04 |
US20180325112A1 (en) | 2018-11-15 |
EP3377486A1 (en) | 2018-09-26 |
US11771088B2 (en) | 2023-10-03 |
CN108349953B (zh) | 2022-06-17 |
US10827755B2 (en) | 2020-11-10 |
MX2018005549A (es) | 2018-11-09 |
BR112018009906B1 (pt) | 2022-05-31 |
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