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CN113527129A - 具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途 - Google Patents

具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途 Download PDF

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CN113527129A
CN113527129A CN202010286890.2A CN202010286890A CN113527129A CN 113527129 A CN113527129 A CN 113527129A CN 202010286890 A CN202010286890 A CN 202010286890A CN 113527129 A CN113527129 A CN 113527129A
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membered
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徐晓勇
李忠
张瑞峰
刘城
陈佃聪
邵旭升
须志平
程家高
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East China University of Science and Technology
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East China University of Science and Technology
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    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract

本发明涉及一种具有杀线虫活性的含三氟烯烃类化合物及其制法和用途。具体地，本发明公开了具有式(I)化合物或其光学异构体、顺反异构体或农药学上可接受的盐，及其制备方法。上述化合物具有优异的杀线虫活性。

Description

具有杀线虫活性的三氟烯烃类化合物及其制备方法和用途
技术领域
本发明属于农药领域。具体地说，本发明涉及一种具有杀线虫活性的三氟烯 烃类化合物及其制备方法和用途。
背景技术
植物寄生线虫是一类危害极大的病原微生物，其分布范围广、种类繁多、环 境适应能力强，可以寄生在植物的根系、茎、叶、种子、幼芽和果实内，能通过取 食活动对寄主植物造成机械损伤，并掠夺寄主植物的营养，尤其是其食道腺分泌物 会导致寄主植物发生一系列病变，还会和其它病原微生物共同侵染寄主植物，引起 复合病害，造成产量损失。在全球范围内，植物寄生线虫每年造成的农业损失高达 1000亿美元以上，严重制约了农业经济的发展。
农业上对线虫的防治手段有很多，目前以化学防治为主。广泛应用的化学杀 线虫剂主要为高毒性、高残留的有机磷或氨基甲酸酯类农药，如硫线磷、丙线磷、 苯线磷、噻唑磷、涕灭威、杀线威和克百威等，对人类与其它非靶标生物的安全性 低，对土壤、水源和农产品也会造成不同程度的污染。另外，由于品种单一，该类 杀线虫剂被过量、频繁使用，已经引起了严重的抗药性，使得线虫的防治难度日益 增加。因此，寻找高效、低毒和环境相容性好的结构新颖的化学杀线虫剂，成为本 领域迫切需要解决的技术问题。
综上所述，本领域迫切需要开发具有杀线虫活性的新化合物。
发明内容
本发明的目的是提供一种高效、低毒和环境相容性好的结构新颖的化学杀线 虫剂。
本发明的另一目的是提供所述化学杀线虫剂的制备方法和应用。
在第一方面，本发明提供式(I)所示化合物、或其光学异构体、顺反异构体或 农药学上可接受的盐：
Figure BDA0002448851040000021
式中，
n为0-5的整数，优选1-3的整数，更优选1；
A为氧或硫原子；
G选自下组：H、取代或未取代的C1-6烷基、取代或未取代的C3-6环烷基、取代 或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的C5-7环烯基、取代 或未取代的5-10元芳基(优选苯基、萘基)、取代或未取代的5元或6元芳杂环基、取 代或未取代的5元或6元脂杂环基；
M为取代或未取代的5-7元芳环、取代或未取代的5-7元碳环、取代或未取代的 5-7元芳杂环或9-12元的稠芳杂环、或取代或未取代的5-7元脂杂环、CH2SN2、CO、 SO，SO2、(CH2)m，其中m为0-5的整数；所述环M的取代基选自下组：H、卤素、 取代或未取代的C1-6烷基或烷氧基、取代或未取代的C3-6环烷基、取代或未取代的 C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的C5-7环烯基、取代或未取代的 5-10元芳基(优选苯基、萘基)、取代或未取代的5元或6元芳杂环基、取代或未取代 的5元或6元脂杂环基；
Q为取代或未取代的5-12元芳环，取代或未取代的5-12元碳环，取代或未取代 的5-12元芳杂环，取代或未取代的5-12元脂杂环(包括全部或部分不饱和的脂杂环)， 取代或未取代的烯基，或选自如下U-1～U-34：
Figure BDA0002448851040000031
其中p为0-7的整数，优选0-5的整数，最优选0-3的整数；
其中R1选自下组：＝O、取代或未取代的C1-6烷基或烷氧基、卤素、取代或未取 代的C3-7环烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取 代的C5-7环烯基、取代或未取代的5-10元芳基(优选苯基、萘基)、取代或未取代的5 元或6元芳杂环基、取代或未取代的5元或6元脂杂环基。
在优选的实施方式中，Q为5-12元芳环或芳杂环。
在进一步的优选实施方式中，Q为5-12元苯并芳杂环或5-12元苯连芳杂环。
在具体的实施方式中，所述化合物如式I-I、I-II、I-III或I-IV所示：
Figure BDA0002448851040000041
其中，m、n、A、G和Q如上文所定义。
在具体的实施方式中，所述化合物如式I-I所示，
其中，m为0或1；
n为1-3的整数；
A为氧原子或硫原子；
G为H、取代或未取代的C1-6烷基或烷氧基(优选卤素取代的烷基)、五元或六 元芳杂环；
Q为取代或未取代的5-12元芳环、取代或未取代的5-12元芳杂环、取代或未取 代的5-12元脂杂环。
在优选的实施方式中，所述芳环是取代或未取代的芳环连芳环，优选取代或 未取代的苯基连苯基；
在优选的实施方式中，所述芳杂环是含氮芳杂环、五元或六元芳杂环、芳环(优 选苯环)并芳杂环、稠芳杂环、芳杂环连芳杂环、芳环连芳杂环；
在优选的实施方式中，所述五元芳杂环包括但不限于：取代或未取代的噁唑、 取代或未取代的噻二唑、取代或未取代的恶二唑、取代或未取代的异噁唑、取代或 未取代的异恶唑啉；
所述六元杂环包括但不限于：取代或未取代的吡啶、取代或未取代的三嗪环、 取代或未取代的恶二唑啉；
所述芳环并芳杂环是苯并芳杂环，包括但不限于：苯并噁唑，苯并三唑、苯 并喹二酮环；
所述稠芳杂环包括但不限于：噻唑并吡唑、三唑并噻二唑，；
所述芳环连芳杂环包括但不限于苯连芳杂环，例如苯连吡唑，苯连噻(恶)唑、 或苯连异恶唑啉；
所述芳杂环连芳杂环包括但不限于：吡嗪联吡啶、吡啶连吡唑。
在具体的实施方式中，所述化合物如式I-I所示，
式中，m为0或1；
n为1-2的整数；
A为氧原子或硫原子；
G为H、取代或未取代的C1-6烷基或烷氧基(优选C1-3烷基或烷氧基)；
Q为取代或未取代的五元或六元芳杂环、取代或未取代的五元或六元脂杂环、 取代或未取代的5-12元芳环(优选苯环)并芳杂环、取代或未取代的5-12元芳杂环连 芳杂环、取代或未取代的5-12元芳环连芳环。
在具体的实施方式中，式I-I所示化合物为选自以下的化合物：
Figure BDA0002448851040000051
Figure BDA0002448851040000061
Figure BDA0002448851040000071
Figure BDA0002448851040000081
Figure BDA0002448851040000091
Figure BDA0002448851040000101
Figure BDA0002448851040000111
Figure BDA0002448851040000121
Figure BDA0002448851040000131
式I-II所示化合物为选自以下的化合物：
Figure BDA0002448851040000132
Figure BDA0002448851040000141
式I-III所示化合物为选自以下的化合物：
Figure BDA0002448851040000142
式I-IV所示化合物为选自以下的化合物：
Figure BDA0002448851040000143
Figure BDA0002448851040000151
在第二方面，本发明提供一种农药组合物，所述农药组合物包含第一方面所 述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，以及任选的农 药学上可接受的赋形剂。
在第三方面，本发明提供第一方面所述的化合物、或其光学异构体、顺反异 构体或农药学上可接受的盐的用途，用于杀线虫或用于制备杀线虫的农药组合物。
在第四方面，本发明提供第二方面所述的农药组合物的用途，用于杀线虫。
在第五方面，本发明提供一种控制和消灭线虫的方法，所述方法包括将有效 量的第一方面所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐 或第二方面所述的农药组合物给予需要控制和消灭线虫的植物或农作物的步骤。
在第六方面，本发明提供第一方面所述的化合物的制备方法，所述化合物采 用以下合成路线制备：
1)当M为取代或未取代的5-7元芳环,取代或未取代的5-7元碳环，取代或未取 代的5-7元芳杂环，或取代或未取代的5-7元杂环，(CH2)m其中m＝0-5时采用以下反 应式所示方法制备：
Figure BDA0002448851040000161
a)将式1-1所示化合物酰氯化得到式1-2所示化合物；
b)将式1-2所示化合物与相应的胺或磺酰胺在碱或缩合剂的存在下反应得到 式1-3所示化合物；
c)将式1-3所示化合物与溴代物在有存在下反应，生成式1-4所示化合物；
或者
2)当M为CH2SN2时采用以下反应式所示方法制备：
Figure BDA0002448851040000162
a)将式2-1所示化合物酰氯化得到式2-2所示化合物；
b)将式2-2所示化合物与相应的硫氰酸铵反应得到相应的异硫氰酸酯，即式 2-3所示化合物；和
c)将式2-3所示化合物与氨基化合物反应生成式2-4所示化合物；
或者
3)当M为SO2时采用以下反应式所示方法制备：
Figure BDA0002448851040000171
a)在有缩合剂存在下，将式3-1所示化合物与相应的磺酰胺反应得到式3-2所 示化合物；
b)将式3-2所示化合物与溴代物在有碱存在下反应生成式3-3所示化合物。
应理解，在本发明范围内中，本发明的上述各技术特征和在下文(如实施例) 中具体描述的各技术特征之间都可以互相组合，从而构成新的或优选的技术方案。 限于篇幅，在此不再一一累述。
附图说明
图1显示了本发明的化合物的构建思路；
图2显示了病情指数分级计算方式。
具体实施方式
本发明人经过长期而深入的研究，设计并合成了一系列结构新颖、具有显著 杀虫活性的含三氟烯烃类化合物。所述化合物能够具备高效、低毒和环境相容性好 等优点。在此基础上，发明人完成了本发明。
基团定义
术语“C1-6烷基”是指具有1-6个碳原子的直链或支链烷基，例如甲基、乙基、丙 基、异丙基、丁基、异丁基、仲丁基、叔丁基、或类似基团。
术语“C2-6烯基”指具有2-6个碳原子的直链或支链的烯基，例如乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、或类似基团。
术语“C2-6炔基”是指具有2-6个碳原子的直链或支链的炔基，例如乙炔基、丙炔基、或类似基团。
术语“C3-7环烷基”指具有3-7个碳原子的环状烷基，例如环丙基、环丁基、环戊 基、环己基、环庚基、或类似基团。
术语“C5-7环烯基”指具有5-7个碳原子的、具有一个或多个双键的环状烯基，例 如环戊烯基、环己烯基、环庚烯基、1,3-环己二烯基、1,4-环己二烯基、或类似基 团。
如本文所用，术语“C1-4烷氧基”指具有1-4个碳原子的直链或支链烷氧基，例如 甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、 或类似基团。
术语“卤素”指氟、氯、溴、或碘。术语“卤代的”指被相同或不同的一个或多个 上述卤原子取代的基团，例如三氟甲基、五氟乙基、七氟异丙基、或类似基团。
术语“环”或“环系”指碳环或杂环。
术语“杂环”指形成所述杂环骨架的原子中至少一个原子不是碳，而是氮、氧 或硫等杂原子。本领域技术人员公知，杂环可分为脂杂环、芳杂环两大类；杂环通 常包含不超过4个氮、不超过2个氧和/或不超过2个硫。除非另外指明，杂环可以是 饱和的、部分不饱和的或完全不饱和的环。
术语“环系”指两个或更多个环并在一起的稠环。
如本文所用，术语“5元或6元杂环基”指含一个或多个选自氮、氧或硫的杂原 子的五元或六元环，例如吡啶基、噻唑基、异噻唑基、噻吩基、呋喃基、吡咯基、 吡唑基、嘧啶基、四氢呋喃基、4,5-二氢噻唑-2-基、2-氰基亚胺基-4-氧-1,3-噻唑烷 -3-基、2-氰基亚胺基-4-氧-1,3-噻嗪烷-3-基、噁唑基、异噁唑基、1H-四唑基、1H-1,2,3- 三唑基、4H-1,2,4-三唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,3,4-噻二唑基、1,2,4- 噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基或四唑基等。
术语“杂环环系”指环系中的至少一个环是杂环的环系。
术语“杂芳环环系”指环系中的至少一个环为芳族环的体系。
术语“烷基”是指烷烃分子中少掉一个氢原子而成的基团；术语“亚烷基”是指烷烃分子中少掉两个氢原子而成的基团。类似地，“亚烯基”、“亚炔基”、“亚环烷基”、 “亚环烯基”、“亚苯基”、“亚萘基”、“亚杂环基”或“亚杂芳二环或三环环系”的定义 类似。
本发明所述的基团除非特别说明是“取代或未取代的”，否则本发明的基团均 可被选自下组的取代基所取代：卤素、氰基、硝基、C1-6烷基、C1-6卤代烷基、C2-6烯基、C2-6卤代烯基、C2-6炔基、C2-6卤代炔基、羟基、羟基C1-4烷基、OR’、Si(R’)3、 NR’R"、C(O)R’、C(O)OR’、C(O)NR’R"、SR’、S(O)mR’、S(O)2NR’R"、OC(O)R’、 OC(O)NR’R"、OS(O)2R’、OS(O)2NR’R"、N(R”)C(O)R’、NCH2R’、N(R”)C(O)NR’R"、 N(R”)S(O)2R’或N(R')S(O)2NR’R"等；
其中，所述的其中，R'、R”各自独立地为H、C1-6烷基或环烷基、C1-6卤代烷基、 C2-6烯基、C2-6卤代烯基、C2-6炔基或C2-6卤代炔基。
惰性溶剂指的是不与原料发生反应的各种溶剂，包括各种直链、支链或环状 的醇，醚或酮，卤代烷，1,4-二氧六环，乙腈，四氢呋喃，N,N-二甲基甲酰胺(DMF)， 二甲基亚砜(DMSO)等。
本发明的具有杀线虫活性的化合物
术语“本发明的活性物质”或“本发明的活性化合物”是指通式(I)所示结构的化合物或农药学上可接受的盐。
在具体的实施方式中，本发明的化合物是通式I所示化合物：
Figure BDA0002448851040000191
式中的n、A、G、M和Q如上文所述。
在进一步的实施方式中，根据通式I中连接桥M的不同，本发明的化合物可分 为几种不同类型的化合物：
当M为(CH2)m，其中m＝0-5时，得到酰胺类化合物I-I，其具体结构示例如上文 所示；
当M为
Figure RE-GDA0002604393530000192
时，得到磺酰胺类化合物I-II，其具体示例如上文所示；
当M为
Figure RE-GDA0002604393530000201
时，得到氨基硫脲类化合物I-III，其具体示例如上文所示；
当M为六元芳(杂)环时，得到化合物I-IV，其中当Q为
Figure RE-GDA0002604393530000202
时得到双 联酰胺类化合物，具体示例如上文所示。
本发明的活性物质能用作控制和消灭广泛的农林植物寄生线虫。在本说明书 中，“杀线虫剂”是具有防治本文提到的所有植物寄生线虫的作用的物质的统称。
植物寄生线虫的例子包括但不限于：根结线虫，如花生根结线虫(Meloidogynearenaria)、奇氏根结线虫(Meloidogyne chitwoodi)、短小根结线虫(Meloidogyneexigua)、北方根结线虫(Meloidogyne hapla)、南方根结线虫(Meloidogyne incognita)、爪哇根结线虫(Meloidogyne javanica)，和其它根结线虫属 (Meloidogyne)；孢囊线虫，如马铃薯金线虫(Globodera rostochiensis)、马铃薯白线 虫(Globodera pallida)、烟草孢囊线虫(Globodera tabacum)，和其它孢囊线虫属 (Globodera)；异皮线虫，如禾谷孢囊线虫(Heterodera avenae)、大豆孢囊线虫 (Heterodera glycines)、甜菜孢囊线虫(Heterodera schachtii)、三叶草孢囊线虫 (Heterodera trifolii)，和其它异皮线虫属(Heterodera)；种瘤线虫，如剪股颖粒线虫 (Anguina funesta)、小麦粒线虫(Anguinatritici)和其它粒线虫属(Anguina)；茎和叶 芽线虫，如水稻干尖线虫(Aphelenchoidesbesseyi)、草莓滑刃线虫(Aphelenchoides fragariae)、菊花滑刃线虫(Aphelenchoidesritzemabosi)，和其它滑刃线虫属 (Aphelenchoides)；刺线虫，如杂草刺线虫(Belonolaimus longicaudatus)和其它针刺 线虫属(Belonolaimus)；松线虫，如松材线虫(Bursaphelenchus xylophilus)和其它 伞滑刃线虫属(Bursaphelenchus)；环形线虫，如环纹线虫属(Criconema)、小环线虫 属(Criconemella)、轮线虫属(Criconemoides)和中环线虫属(Mesocriconema)；球 茎线虫，如腐烂茎线虫(Ditylenchus destructor)、甘薯茎线虫(Ditylenchus dipsaci)、 蘑菇茎线虫(Ditylenchus myceliophagus)，和其它茎线虫属(Ditylenchus)；锥线虫， 如锥线虫属(Dolichodorus)；螺旋线虫，如双宫螺旋线虫(Helicotylenchus dihystera)、多带螺旋线虫(Helicotylenchus multicintus)，和其它螺旋线虫属 (Helicotylenchus)；鞘线虫，如鞘线虫属(Hemicycliophora)和半轮线虫属(Hemicriconemoides)；冠线虫，如哥伦比亚纽带线虫(Hoploaimus columbus)和其它 纽带线虫属(Hoploaimus)；伪根瘤线虫，如异常珍珠线虫(Nacobbus aberrans)和 其它珍珠线虫属(Nacobbus)；针线虫，如逸去长针线虫(Longidorus elongatus)和 其它长针线虫属(Longidorus)；钉线虫，如钉线虫属(Paratylenchus)；根腐线虫， 如最短尾短体线虫(Pratylenchus brachyurus)、咖啡短体线虫(Pratylenchus coffee)、 玉米短体线虫(Pratylenchus zeae)、穿刺短体线虫(Pratylenchus penetrans)，和其 它短体线虫属(Pratylenchus)；穿孔线虫，如香蕉穿孔线虫(Radopholus similis)和 其它穿孔线虫属(Radopholus)；肾形线虫，如肾形肾状线虫(Rotylenchus robustus) 和其它肾形线虫属(Rotylenchus)；残根线虫，如原始毛刺线虫(Trichodorus primitivus)和其它毛刺线虫属(Trichodorus)；矮化线虫，如克莱顿矮化线虫 (Tylenchorhynchus claytoni)、不定矮化线虫(Tylenchorhynchus dubius)，和其它矮化 线虫属(Tylenchorhynchus)；柑桔线虫，如柑桔半穿刺线虫(Tylenchulus semipenetrans)和其它小垫刃线虫属(Tylenchulus)；剑线虫，如美洲剑线虫 (Xiphinema americanum)、标准剑线虫(Xiphinema index)、裂尾剑线虫(Xiphinema diversicaudatum)，和其它剑线虫属(Xiphinema)。
本发明涉及的化合物尤其对南方根结线虫(Meloidogyne incognita)有较好的防治效果。
含本发明活性物质的杀线虫剂组合物
可将本发明的活性物质以常规的方法制备成杀线虫剂组合物。这些活性化合 物可做成常规的制剂，例如溶液剂、乳剂、混悬剂、粉剂、泡沫剂、糊剂、颗粒剂、 气雾剂、用活性物质浸渍的天然的和合成的材料、在多聚物中的微胶囊、用于种子 的包衣复方、和与燃烧装置一块使用的制剂，例如烟熏药筒、烟熏罐和烟熏盘，以 及ULV冷雾(Cold mist)和热雾(Warm mist)制剂。
这些制剂可用已知的方法生产，例如，将活性化合物与扩充剂混合，这些扩 充剂就是液体的或液化气的或固体的稀释剂或载体，并可任意选用表面活性剂即乳 化剂和/或分散剂和/或泡沫形成剂。例如在用水作扩充剂时，有机溶剂也可用作助 剂。
用液体溶剂作稀释剂或载体时，基本上是合适的，如：芳香烃类，例如二甲 苯、甲苯或烷基萘；氯化的芳香或氯化的脂肪烃类，例如氯苯、氯乙烯或二氯甲烷； 脂肪烃类，例如环己烷或石蜡，例如矿物油馏分；醇类，例如乙醇或乙二醇以及它 们的醚和脂类；酮类，例如丙酮、甲乙酮、甲基异丁基酮或环已酮；或不常用的极 性溶剂，例如二甲基甲酰胺和二甲基亚砜，以及水。
液化气的稀释剂或载体，指的是在常温常压下将成为气体的液体，例如气溶 胶推进剂，如卤化的烃类以及丁烷、丙烷、氮气和二氧化碳。
固体载体可用磨碎的天然的矿物质，例如高岭土、粘土、滑石、石英、活性 白土、蒙脱土、或硅藻土；和磨碎的合成的矿物质，例如高度分散的硅酸、氧化铝 和硅酸盐。供颗粒用的固体载体是碾碎的和分级的天然锆石，例如方解石、大理石、 浮石、海泡石和白云石，以及无机和有机粗粉合成的颗粒，和有机材料例如锯木屑、 椰子壳、玉米棒子和烟草梗的颗粒等。
非离子的和阴离子的乳化列可用作乳化剂和/或泡沫形成剂。例如聚氧乙烯- 脂肪酸酯类，聚氧乙烯-脂肪醇醚类，例如烷芳基聚乙二醇醚类，烷基磺酸酯类， 烷基硫酸酯类，芳基磺酸酯类以及白蛋白水解产物。分散剂包括木质素亚硫酸盐废 液和甲基纤维素。
在制剂中可以用粘合剂，例如羧甲基纤维素和以粉末、颗粒或乳液形式的天 然和合成的多聚物，例如阿拉伯胶、聚乙烯基醇和聚乙烯醋酸酯。
可以用着色剂例如无机染料，如氧化铁、氧化钴和普鲁士蓝；有机染料，如 偶氮染料或金属酞菁染料；和用痕量营养剂，如铁、锰、硼、铜、钴、铝和锌的盐 等。
本发明的这些活性化合物可与其他活性化合物制成一种混合物存在于它们的 商品制剂中或从这些制剂制备的使用剂型中，这些其他的活性化合物为杀虫剂、杀 菌剂、杀真菌剂、除草剂、生长控制剂等。杀虫剂包括，例如磷酸酯类、氨基甲酸 酯类、氯化烃类以及由微生物产生的物质，如阿维菌素等，杀真菌剂包括甲氧基丙 烯酸酯类、酰胺类、三唑类等。
此外，本发明的这些活性化合物也可与增效剂制成一种混合物存在于它们的 商品制剂中或从这些制剂制备的使用剂型中，这些增效剂是提高活性化合物作用的 化合物，由于活性化合物本身有活性，也可不必加增效剂。
这些制剂通常含有占所述杀线虫剂组合物总重量的0.001-99.99重量％，优选0.01-99.9重量％，更优选0.05-90重量％的本发明的活性化合物。商品制剂或使用剂 型中的活性化合物的浓度可在广阔的范围内变动。使用剂型中的活性化合物的浓度 可从0.0000001-100％(g/v)，最好在0.0001与1％(g/v)之间。
本发明化合物的制备方法
本发明通式所示化合物可通过如下的方法制得，然而该方法的条件，例如反 应物、溶剂、碱、所用化合物的量、反应温度、反应所需时间等不限于下面的解释。 本发明化合物还可以任选将在本说明书中描述的或本领域已知的各种合成方法组 合起来而方便的制得，这样的组合可由本发明所属领域的技术人员容易的进行。如 果可行，试剂可以通过商业途径购买。
本发明的化合物中典型的实施方案可以使用下述的通用反应方案来合成。从 本文中给出的描述中显而易见的是，可以通过用具有类似结构的其他材料代替来改 变通用方案从而获得相应的不同产物。合成方法可以根据需要以提供大量的生产。 原料可以通过商业方法获得或者使用公开的方法来合成。本文给出的实施例，通过 简单的检验步骤，最终产物的特征通常使得必要原料的特征显而易见。
合成反应参数可以使用，例如，以下的一般方法和程序，从容易获得的起始 材料来制备本发明的化合物。将认识到在给出典型或优化方法条件(即，反应温度、 时间、反应物的摩尔比、溶剂、催化剂、压力等)的情况下，也可以使用其他的方 法条件，除非另外指出。最佳的反应条件可以随所用的特定反应物或溶剂而变化， 但是这样的条件可以由本领域技术人员通过常规优化程序来决定。
用于以下反应的原料通常是已知的化合物，或可以通过已知的步骤或其显而 易见的修饰来制备。例如，很多原料可以通过商业供应者获得，其他的可以通过在 标准参考文献正文中描述的步骤或者显而易见的修改来制备。
在本发明的制备方法中，各反应通常在惰性溶剂中，反应温度-20～120℃(优 选-10～0℃或20～30℃或80～100℃)下进行。反应时间通常为2～24小时，较佳地 为4～18小时，可以根据反应需要适当的延长反应时间，具体反应时间根据反应程 度来定。
反应中所用的碱包括(但并不限于)：三乙胺、吡啶、二异丙基乙基胺、二乙胺、 哌啶、哌嗪、吗啉、N-甲基吗啉、三乙烯二胺(DABCO)、1,8-二氮杂二环[5.4.0]十 一碳-7-烯(DBU)、1,5-二氮杂二环[4.3.0]壬-5-烯(DBN)、碳酸钾、碳酸氢钾、碳酸 钠、碳酸氢钠、碳酸铯、氢氧化钠、氢氧化钾、甲醇钠、乙醇钠，或其组合。
反应中所用缩合剂包括(但不限于)：4-二甲氨基吡啶(4-DMAP、PyBop)、叠氮 磷酸二苯酯(DPPA)、二环己基碳二亚胺(DCC)、HATU、二苯基次膦酰氯(DPP-Cl)。
合成路线：
一、当M为取代或未取代的5-7元芳环,取代或未取代的5-7元碳环，取代或未 取代的5-7元芳杂环，或取代或未取代的5-7元杂环，(CH2)m其中m＝0-5时采用方案 一中方法。
方案1：
Figure BDA0002448851040000241
在一个方案中，由1-1酰氯化，然后与相应的胺或磺酰胺在碱或缩合剂的存在 下得到1-3，1-3再与溴代物在碱的条件下反应生成化合物1-4。
当M为CH2SN2时采用方案二中方法。
方案二：
Figure BDA0002448851040000242
在一个方案中，由2-1酰氯化，然后与相应的硫氰酸铵反应得到相应的异硫氰 酸酯2-3，2-3再与氨基化合物反应生成化合物2-4。
当M为SO2时采用方案三：
Figure BDA0002448851040000243
在一个方案中，由3-1在缩合剂存在下，与相应的磺酰胺反应得到3-2，3-2再 与溴代物在碱的条件下反应生成化合物3-3。
合成实施例
1、制备I-I化合物
以制备I-I-2 N-(5-氯噻唑-2-基)-4,5,5-三氟戊烯-4-酰胺为例。
(1)、I-I-2中间体的制备。
4,5,5-三氟戊烯酰氯的合成
Figure BDA0002448851040000251
将4,5,5-三氟戊烯酰氯2mmol，二氯甲烷15mL加入至50mL单口瓶，冰浴滴加2.5mmol草酰氯的二氯甲烷溶液，滴加完毕后加入0.05mL DMF。室温搅拌3h。反 应完成后蒸馏除去二氯甲烷得粗品4,5,5-三氟戊烯酰氯，收率91％。未经纯化直接 投下一步反应。
2-氨基-4-氯噻唑的合成
Figure BDA0002448851040000252
将2-氨基噻唑5mmol，乙酸10mL，NCS 6mmol加入至100mL单口瓶，室温 搅拌反应，TLC跟踪反应，反应完成后将反应液到入至50mL蒸馏水中，用饱和碳 酸氢钠水溶液调节PH＝7。用二氯甲烷萃取(15mL×3)，合并有机层，用无水硫酸钠 干燥，抽滤，浓缩滤液。石油醚/乙酸乙酯＝3/1柱层析得2-氨基-4-氯噻唑纯品，收 率72％。
(2)、I-I-2的制备
Figure BDA0002448851040000253
N-(5-氯噻唑-2-基)-4,5,5-三氟戊烯-4-酰胺为例。将2-氨基-5-氯噻唑3mmol，4,5,5-三氟戊烯酰氯3mmol，三乙胺4.5mmol，二氯甲烷20mL，加入至单口瓶中， 室温搅拌反应。TLC跟踪，反应完成后，减压除去溶剂，向残留物中加入饱和氯化 铵水溶液30mL，二氯甲烷(15mL×3)萃取，合并有机相，用无水硫酸钠干燥，抽滤， 收集并浓缩滤液，石油醚乙酸乙酯柱层析得纯品N-(5-氯噻唑-2-基)-4,5,5-三氟戊烯 -4-酰胺。
2、制备I-II化合物
以制备I-II-1 4,5,5-三氟-N-(噻唑-2-基磺酰基)戊-4-烯胺为例
Figure BDA0002448851040000261
将噻唑-2-磺酰胺1.7mmol，4,5,5-三氟戊烯酸3mmol，三乙胺4.5mmol，二氯 甲烷20mL，加入至单口瓶中，室温搅拌反应。TLC跟踪，反应完成后，减压除去 溶剂，向残留物中加入饱和氯化铵水溶液30 mL，二氯甲烷(15mL×3)萃取，合并有 机相，用无水硫酸钠干燥，抽滤，收集并浓缩滤液，石油醚乙酸乙酯柱层析得纯品 N-(5-氯噻唑-2-基)-4,5,5-三氟戊烯-4-酰胺。
3、制备I-III化合物
以制备I-III-1 4,5,5-三氟-N-(2-(噻唑-2-基)肼-1-硫代羰基)戊-4-烯酰胺为例
(1)中间体4,5,5-三氟戊-4-烯酰基异硫氰酸酯的制备
Figure BDA0002448851040000262
将硫氰酸铵2mmol，4,5,5-三氟戊烯酰氯2mmol，碳酸二甲酯20mL，加入至 单口瓶中，搅拌加热至回流。30min后，停止加热，冷却至室温。减压除去溶剂， 向残留物中加入饱和氯化钠水溶液30mL，二氯甲烷(15mL×3)萃取，合并有机相， 用无水硫酸钠干燥，抽滤，收集并浓缩滤液，得粗品4,5,5-三氟戊-4-烯酰基异硫氰 酸酯。
(2)4,5,5-三氟-N-(2-(噻唑-2-基)肼-1-硫代羰基)戊-4-烯酰胺的制备
Figure BDA0002448851040000263
将4,5,5-三氟戊-4-烯酰基异硫氰酸酯2mmol，2-噻唑肼2mmol，乙酸乙酯20 mL，加入至单口瓶中，搅拌冷却至0℃反应。TLC跟踪，反应完成后，加入饱和氯 化钠水溶液30mL，萃取，合并有机相，用无水硫酸钠干燥，抽滤，收集并浓缩滤 液，柱层析得4,5,5-三氟-N-(2-(噻唑-2-基)肼-1-硫代羰基)戊-4-烯酰胺。
4、制备I-IV化合物
以制备I-IV-6 N2,N6-双(4,5,5-三氟戊-4-烯-1-基)吡嗪-2,6-酰胺为例
Figure BDA0002448851040000271
将2,6-二氨基吡嗪1.5mmol，4,5,5-三氟戊烯酸3mmol，吡啶4.5mmol，二氯甲 烷20mL，加入至单口瓶中，室温搅拌反应。TLC跟踪，反应完成后，减压除去溶 剂，向残留物中加入饱和氯化铵水溶液30mL，二氯甲烷(15mL×3)萃取，合并有机 相，用无水硫酸钠干燥，抽滤，收集并浓缩滤液，石油醚乙酸乙酯柱层析得纯品 N2,N6-双(4,5,5-三氟戊-4-烯-1-基)吡嗪-2,6-酰胺。
目标化合物核磁数据：
表5：化合物I-I核磁数据
Figure BDA0002448851040000273
Figure BDA0002448851040000272
Figure BDA0002448851040000281
Figure BDA0002448851040000291
Figure BDA0002448851040000301
Figure BDA0002448851040000311
Figure BDA0002448851040000321
Figure BDA0002448851040000331
Figure BDA0002448851040000341
Figure BDA0002448851040000351
表6：化合物I-II核磁数据：
Figure BDA0002448851040000353
Figure BDA0002448851040000352
Figure BDA0002448851040000361
表7：化合物I-III核磁数据
Figure BDA0002448851040000363
Figure BDA0002448851040000362
Figure BDA0002448851040000371
表8：化合物I-IV核磁数据：
Figure BDA0002448851040000373
Figure BDA0002448851040000372
Figure BDA0002448851040000381
测试实施例.本发明化合物的杀线虫活性测试
根结线虫属于线虫门、垫刃目(Tylenchida)、垫刃亚目、异皮总科、异皮科(Heteroderidea)、根结线虫亚科(Meloidogyninae)、根结线虫属，是一种危害严重的 植物寄生线虫。
活体活性
以南方根结线虫(Meloidogyne incognita)为测试对象，以黄瓜苗为供试寄主，采用试管种植法测试。
操作过程：将待试样品按所需浓度配成药液待用，并准备好足量的根结线虫 二龄幼虫。将一周龄的黄瓜苗种植到试管中后，向试管中加入适量配好的药液，并 向每支试管中接入约2000条幼虫。试管置于20～25℃，10小时光照下培养，45天 后调查结果，计数每株植株根系上的根结数。每个样品重复试验3次，每次试验每 个样品做4个重复处理。
以蒸馏水为空白对照，蒸馏水加根结线虫为阴性对照，以阿维菌素溶液为阳 性对照。
病情指数分级计算参照图2。
化合物活体杀线虫活性：
表9：化合物I-I活体活性：
Figure BDA0002448851040000392
Figure BDA0002448851040000391
Figure BDA0002448851040000401
Figure BDA0002448851040000411
表10：化合物I-II活体活性：
Figure BDA0002448851040000413
Figure BDA0002448851040000412
Figure BDA0002448851040000421
表11：化合物I-III活体活性：
Figure BDA0002448851040000424
Figure BDA0002448851040000422
表12：化合物I-IV活体活性：
Figure BDA0002448851040000425
Figure BDA0002448851040000423
离体活性
以南方根结线虫(Meloidogyne incognita)为测试对象，在96孔板中进行离体试验。
将待测化合物用丙酮稀释成一定浓度的溶液，再用一定量水将其稀释成测试 浓度。将药液与一定量南方根结线虫的二龄幼虫加入至96孔板，每个孔中不少于50 条幼虫。配制完成后将96孔板放置在25℃恒温箱中，在72h观察并记录线虫的死亡 情况。在测试中，每个化合物平行测定两次，以丙酮的水溶液作为空白对照，以氟 噻虫砜作为阳性对照。死亡率见下表。
化合物离体杀线虫活性：
表13：化合物I-I离体活性：
Figure BDA0002448851040000432
Figure BDA0002448851040000431
Figure BDA0002448851040000441
Figure BDA0002448851040000451
Figure BDA0002448851040000461
Figure BDA0002448851040000471
表14：化合物I-II离体活性：
Figure BDA0002448851040000474
Figure BDA0002448851040000472
表15：化合物I-III离体活性
Figure BDA0002448851040000475
Figure BDA0002448851040000473
表16：化合物I-IV离体活性：
Figure BDA0002448851040000482
Figure BDA0002448851040000481
通过以上表格总结的活性可见，本发明的化合物具有非常好的杀线虫活性， 在低达40ppm浓度下即可表现出明显的杀线虫效果。
在本发明提及的所有文献都在本申请中引用作为参考，就如同每一篇文献被 单独引用作为参考那样。此外应理解，在阅读了本发明的上述讲授内容之后，本领 域技术人员可以对本发明作各种改动或修改，这些等价形式同样落于本申请所附权 利要求书所限定的范围。

Claims (10)

1.式(I)所示化合物、或其光学异构体、顺反异构体或农药学上可接受的盐：
Figure FDA0002448851030000011
式中，
n为0-5的整数，优选1-3的整数，更优选1；
A为氧或硫原子；
G选自下组：H、取代或未取代的C1-6烷基、取代或未取代的C3-6环烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的C5-7环烯基、取代或未取代的5-10元芳基(优选苯基、萘基)、取代或未取代的5元或6元芳杂环基、取代或未取代的5元或6元脂杂环基；
M为取代或未取代的5-7元芳环、取代或未取代的5-7元碳环、取代或未取代的5-7元芳杂环或9-12元的稠芳杂环、或取代或未取代的5-7元脂杂环、CH2SN2、CO、SO，SO2、(CH2)m，其中m为0-5的整数；所述环M的取代基选自下组：H、卤素、取代或未取代的C1-6烷基或烷氧基、取代或未取代的C3-6环烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的C5-7环烯基、取代或未取代的5-10元芳基(优选苯基、萘基)、取代或未取代的5元或6元芳杂环基、取代或未取代的5元或6元脂杂环基；
Q为取代或未取代的5-12元芳环，取代或未取代的5-12元碳环，取代或未取代的5-12元芳杂环，取代或未取代的5-12元脂杂环(包括全部或部分不饱和的脂杂环)，取代或未取代的烯基，或选自如下U-1～U-34：
Figure FDA0002448851030000021
其中p为0-7的整数，优选0-5的整数，最优选0-3的整数；
其中R1选自下组：＝O、取代或未取代的C1-6烷基或烷氧基、卤素、取代或未取代的C3-7环烷基、取代或未取代的C2-6烯基、取代或未取代的C2-6炔基、取代或未取代的C5-7环烯基、取代或未取代的5-10元芳基(优选苯基、萘基)、取代或未取代的5元或6元芳杂环基、取代或未取代的5元或6元脂杂环基。
2.如权利要求1所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，其特征在于，所述化合物如式I-I、I-II、I-III或I-IV所示：
Figure FDA0002448851030000031
其中，m、、n、A、G和Q如权利要求1中所定义。
3.如权利要求2所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，其特征在于，所述化合物如式I-I所示，
其中，m为0或1；
n为1-3的整数；
A为氧原子或硫原子；
G为H、取代或未取代的C1-6烷基或烷氧基(优选卤素取代的烷基)、五元或六元芳杂环；
Q为取代或未取代的5-12元芳环、取代或未取代的5-12元芳杂环、取代或未取代的5-12元脂杂环。
4.如权利要求3所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，其特征在于，
式中，m为0或1；
n为1-2的整数；
A为氧原子或硫原子；
G为H、取代或未取代的C1-6烷基或烷氧基(优选C1-3烷基或烷氧基)；
Q为取代或未取代的五元或六元芳杂环、取代或未取代的五元或六元脂杂环、取代或未取代的5-12元芳环(优选苯环)并芳杂环、取代或未取代的5-12元芳杂环连芳杂环、取代或未取代的5-12元芳环连芳环。
5.如权利要求2所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，其特征在于，式I-I所示化合物为选自以下的化合物：
Figure FDA0002448851030000041
Figure FDA0002448851030000051
Figure FDA0002448851030000061
Figure FDA0002448851030000071
Figure FDA0002448851030000081
Figure FDA0002448851030000091
Figure FDA0002448851030000101
Figure FDA0002448851030000111
Figure FDA0002448851030000121
式I-II所示化合物为选自以下的化合物：
Figure FDA0002448851030000122
式I-III所示化合物为选自以下的化合物：
Figure FDA0002448851030000123
Figure FDA0002448851030000131
式I-IV所示化合物为选自以下的化合物：
Figure FDA0002448851030000132
Figure FDA0002448851030000141
6.一种农药组合物，所述农药组合物包含权利要求1-5中任一项所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐，以及任选的农药学上可接受的赋形剂。
7.权利要求1-5中任一项所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐的用途，用于杀线虫或用于制备杀线虫的农药组合物。
8.权利要求6所述的农药组合物的用途，用于杀线虫。
9.一种控制和消灭线虫的方法，其特征在于，所述方法包括将有效量的权利要求1-5中任一项所述的化合物、或其光学异构体、顺反异构体或农药学上可接受的盐或权利要求6所述的农药组合物给予需要控制和消灭线虫的植物或农作物的步骤。
10.权利要求1-5中任一项所述的化合物的制备方法，其特征在于，所述化合物采用以下合成路线制备：
1)当M为取代或未取代的5-7元芳环,取代或未取代的5-7元碳环，取代或未取代的5-7元芳杂环，或取代或未取代的5-7元杂环，(CH2)m其中m＝0-5时采用以下反应式所示方法制备：
Figure FDA0002448851030000142
a)将式1-1所示化合物酰氯化得到式1-2所示化合物；
b)将式1-2所示化合物与相应的胺或磺酰胺在碱或缩合剂的存在下反应得到式1-3所示化合物；
c)将式1-3所示化合物与溴代物在有存在下反应，生成式1-4所示化合物；
或者
2)当M为CH2SN2时采用以下反应式所示方法制备：
Figure FDA0002448851030000151
a)将式2-1所示化合物酰氯化得到式2-2所示化合物；
b)将式2-2所示化合物与相应的硫氰酸铵反应得到相应的异硫氰酸酯，即式2-3所示化合物；和
c)将式2-3所示化合物与氨基化合物反应生成式2-4所示化合物；
或者
3)当M为SO2时采用以下反应式所示方法制备：
Figure FDA0002448851030000152
a)在有缩合剂存在下，将式3-1所示化合物与相应的磺酰胺反应得到式3-2所示化合物；
b)将式3-2所示化合物与溴代物在有碱存在下反应生成式3-3所示化合物。
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Inventor after: Shao Xusheng

Inventor after: Xu Zhiping

Inventor after: Cheng Jiagao

Inventor before: Xu Xiaoyong

Inventor before: Li Zhong

Inventor before: Zhang Ruifeng

Inventor before: Liu Cheng

Inventor before: Chen Diancong

Inventor before: Shao Xusheng

Inventor before: Xu Zhiping

Inventor before: Cheng Jiagao

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