CN113754563B - 一种2-氰基丙烯酸酯类化合物、其制备方法及应用 - Google Patents
一种2-氰基丙烯酸酯类化合物、其制备方法及应用 Download PDFInfo
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- CN113754563B CN113754563B CN202010493009.6A CN202010493009A CN113754563B CN 113754563 B CN113754563 B CN 113754563B CN 202010493009 A CN202010493009 A CN 202010493009A CN 113754563 B CN113754563 B CN 113754563B
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- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/41—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by carboxyl groups, other than cyano groups
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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Abstract
本发明公开了一种通式(I)表示的2‑氰基丙烯酸酯类化合物：
Description
技术领域
本发明属于杀菌剂领域，具体涉及一种2-氰基丙烯酸酯类化合物及其对真菌病害的防治应用。
背景技术
2-氰基丙烯酸酯类化合物不仅具有抗肿瘤等医药活性，而且具有除草、抗真菌、抗植物病毒等农药活性，因此在农药创制领域一直备受重视。例如杀菌剂品种氰烯菌酯，可以有效防治小麦赤霉病、水稻恶苗病等病害。
江苏省农药研究所专利CN1160318C公开了一类如下通式(A)所示的2-氰基-3-取代苯基丙烯酸酯类化合物，该化合物可以抑制小麦赤霉病菌菌丝生长，从而起到防治小麦赤霉病的效果。
江苏省农药研究所专利CN109879834A还公开了一类如下通式(B)所示的2-氰基-3-氨基丙烯酸酯类化合物，该类曼尼希碱类杀菌剂能抑制菌丝生长，对小麦赤霉病等镰刀菌引起的植物病害具有防治效果。
江苏省农药研究所专利CN109879841A还公开了一类如以下通式(C)所示的(Z)-3-亚氨基-1-丙烯醇类化合物，该化合物对引起植物病害的镰刀菌具有优异的专杀活性，如对小麦赤霉病、黄瓜炭疽病、黄瓜枯萎病、花生根腐病、西瓜枯萎病、水稻恶苗病、芒果炭疽病等由镰刀菌引起的植物病害具有防效，尤其是对小麦赤霉病，能够抑制菌丝生长的同时还能降低小麦赤霉病毒素(DON)的产生。
由此可知，上述公开专利中为了防治小麦赤霉病等真菌病害，均是通过抑制菌丝生长来实现，尤其是丙烯酸酯类化合物和丙烯醇类化合物。而本领域技术人员知悉，真菌的生长包括孢子萌发和菌丝生长两个阶段，从孢子萌发阶段对真菌进行抑制才能从源头上更高效率、更好效果地对真菌病害进行防治。
发明内容
为了解决上述技术问题，本发明提出了下式(I)所示的2-氰基丙烯酸酯类化合物：
所述2-氰基丙烯酸酯类化合物中，与氰基和烷氧羰基相连的双键可以为Z式或E式构型，也即，本发明的2-氰基丙烯酸酯类化合物可以是顺式结构或反式结构。
本发明提供的通式(I)所示的2-氰基丙烯酸酯类化合物中，X1、X2、X3、X4独立地选自氢、C1-C10烷基、卤代C1-C10烷基、C3-C10环烷基、卤代C3-C10环烷基、C1-C10烷氧基、卤代C1-C10烷氧基、C2-C10烯基、C2-C10炔基、卤素、硝基、氰基、羟基、巯基、羧基、C1-C10烷氧基羰基。
作为一种优选的方式，所述取代基X1、X2、X3、X4独立地选自氢、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、卤代C3-C6环烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C2-C6烯基、C2-C6炔基、卤素、硝基、氰基、羟基、巯基、羧基、C1-C6烷氧基羰基。
作为进一步优选的方式，所述取代基X1、X2、X3、X4独立地选自氢、C1-C3烷基、卤代C1-C3烷基、C3-C6环烷基、卤代C3-C6环烷基、C1-C3烷氧基、卤代C1-C3烷氧基、卤素、硝基、氰基、羟基、巯基、羧基、C1-C3烷氧基羰基。
作为更进一步优选的方式，所述取代基X1、X2、X3、X4独立地选自氢、C1-C3烷基、卤代C1-C3烷基、C1-C3烷氧基、卤代C1-C3烷氧基、卤素、硝基、氰基、羟基、巯基、羧基、C1-C3烷氧基羰基。
本发明提供的通式(I)所示的2-氰基丙烯酸酯类化合物中，Y1、Y2独立地选自氢、C1-C10烷基、卤代C1-C10烷基、C3-C6环烷基、卤代C3-C10环烷基、C1-C10烷氧基、卤代C1-C10烷氧基、卤素、氰基、硝基、羟基、巯基。
作为一种优选的方式，所述取代基Y1、Y2独立地选自氢、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、卤代C3-C6环烷基、C1-C6烷氧基、卤代C1-C6烷氧基、卤素、氰基、硝基、羟基、巯基。
作为进一步优选的方式，所述取代基Y1、Y2独立地选自氢、C1-C3烷基、卤代C1-C3烷基、C3-C6环烷基、卤代C3-C6环烷基、C1-C3烷氧基、卤代C1-C3烷氧基、卤素、氰基、硝基、羟基、巯基。
作为更进一步优选的方式，所述取代基Y1、Y2独立地选自氢、卤素、羟基、巯基。
本发明提供的通式(I)所示的2-氰基丙烯酸酯类化合物中，R独立地选自氢、C1-C10烷基、卤代C1-C10烷基、C3-C10环烷基、卤代C3-C10环烷基、C2-C10烯基、C2-C10炔基、苯基或如下R1至R3所示结构中的一种：
作为一种优选的方式，所述取代基R独立地选自氢、C1-C6烷基、卤代C1-C6烷基、C3-C6环烷基、卤代C3-C6环烷基、C2-C6烯基、C2-C6炔基、苯基或R1至R3所示结构中的一种。
作为进一步优选的方式，所述取代基R独立地选自氢、C1-C3烷基、卤代C1-C3烷基、C3-C6环烷基、卤代C3-C6环烷基、苯基或R1至R3所示结构中的一种。
作为更进一步优选的方式，所述取代基R独立地选自氢、C1-C3烷基、卤代C1-C3烷基或R1至R2所示结构中的一种。
上述R1至R3所示的结构中，p为1～10的整数。
作为一种优选的方式，所述p为1～6的整数。
作为进一步优选的方式，所述p为1～3的整数。
作为更进一步优选的方式，所述p为1～2的整数。
作为最为优选的实施方式，上述通式(I)所示的2-氰基丙烯酸酯类化合物选自以下结构式所示化合物中的至少一种，
本发明所述的取代基中：烷基是指直链或支链形式，例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、特丁基、正戊基、异戊基、正己基等基团；环烷基是指包括环状链形式，例如环丙基、环丁基、环戊基、环己基等基团；烯基是指直链或支链形式，例如乙烯基、1-丙烯基、烯丙基、异丙烯基、1-丁烯基、1，3-丁二烯基、1-己烯基等基团；炔基是指直链或支链形式，例如乙炔基、1-丙炔基、炔丙基、2-丁炔基、2-戊炔基、3-己炔基等基团；卤代烷基是指烷基被一个或多个卤原子取代的基团；烷氧基是指烷基末端连有氧原子的基团，例如甲氧基、乙氧基、正丙氧基、异丙氧基、特丁氧基等；卤代烷氧基是指烷基被一个或多个卤原子取代，末端连有氧原子的基团；卤素是指氟、氯、溴、碘。
本发明所述的通式(I)所示的2-氰基丙烯酸酯类化合物，当与氰基和烷氧羰基相连的双键为Z式构型时，其具有以下结构式(I-1)，
索引表1列举了结构式(I-1)表示的典型化合物，但索引表1所述典型化合物并不限制本发明的范围。
索引表1
本发明所述的通式(I)表所示的2-氰基丙烯酸酯类化合物，当与氰基和烷氧羰基相连的双键为E式构型时，其具有以下结构式(I-2)，
索引表2列举了结构式(I-2)表示的典型化合物，但索引表2所述典型化合物并不限制本发明的范围。
索引表2
以下表3为索引表1和索引表2中所述部分化合物的核磁数据。表3中所述化合物编号与索引表1和索引表2中所述化合物编号相对应，即：表3所述化合物编号1的化合物与索引表1所述化合物编号1的化合物一致。表3中，s为单峰，d为双峰，dd为双二重峰，t为三重峰，td为三重二重峰，q为四重峰，m为多重峰。
表3化合物核磁数据
本发明还提供了一种上述结构式(I)所示的2-氰基丙烯酸酯类化合物的制备方法，首先由氰乙酸乙酯与式(II)表示的取代1-茚酮在催化剂、脱水剂的存在下，在有机溶剂中通过缩合反应制备式(III)表示的中间体，式(III)表示的中间体然后在卤代试剂、碱的存在下，在有机溶剂中通过卤代、消去等反应一锅法或分步制备结构式(I)所示的2-氰基丙烯酸酯类化合物：
所述各取代基的定义及其优选如前所述。
所述制备方法中，本领域常用的催化剂、卤代试剂、碱、溶剂等均能用于本发明。
优选的是，所述催化剂选自四氯化钛、三氯化铝、三氟化硼、二氯化锌、三氯化铁、三溴化铁和四氯化锡中的至少一种；当Y为氯时，所述卤代试剂选自氯气、三氯化磷、二氯化二硫和N-氯代丁二酰亚胺中的至少一种；当Y为溴时，所述卤代试剂选自溴素、氢溴酸、N-溴代丁二酰亚胺和二溴海因中的至少一种；当Y为氟时，所述卤代试剂选自氟化钾、N-氟代双苯磺酰胺和选择性氟试剂(SELECTFLUOR)中的至少一种；所述碱选自4-二甲氨基吡啶、吡啶、哌啶、N,N-二异丙基乙基胺、二乙胺、三乙胺和三乙烯二胺中的至少一种；所述溶剂选自二氯甲烷、三氯甲烷、甲苯、苯、乙腈、丙酮、N,N-二甲基甲酰胺、四氢呋喃和二氧六环中的至少一种。
本发明还提供一种通式(I)所示的2-氰基丙烯酸酯类化合物的应用，所述通式(I)所示的2-氰基丙烯酸酯类化合物适合用于防治真菌病害。所述2-氰基丙烯酸酯类化合物用于抑制真菌的孢子萌发，从而防治真菌病害。
当所述通式(I)所示的2-氰基丙烯酸酯类化合物用于防治真菌病害时，所述通式(I)所示的2-氰基丙烯酸酯类化合物用于防治由镰刀菌属、布氏白粉菌属、驼孢锈属、盘梗霉属、疫霉属、链格孢属、芽枝霉属、革菌属、顶囊壳属、轴黑粉菌属、多黑粉菌属、曲霉菌属、壳二孢属、葡萄孢属、丝核菌属和黄单孢菌属中的至少一种引起的病害。
当所述通式(I)所示的2-氰基丙烯酸酯类化合物用于防治真菌病害时，所述通式(I)所示的2-氰基丙烯酸酯类化合物用于防治赤霉病、稻瘟病、灰霉病、炭疽病、恶苗病、霜霉病和白粉病中的至少一种病害。
本发明还提供一种农药制剂，所述农药制剂含有0.001％-99.99％重量百分比的通式(I)所示的2-氰基丙烯酸酯类化合物。所述农药制剂，可以被配制成乳油、悬浮剂、水悬剂、微乳剂、(水)乳剂、粉剂、可湿性粉剂、可溶性粉剂、(水分散性)颗粒剂或胶囊剂等。
本发明提供的农药制剂，除含有0.001％-99.99％重量百分比的通式(I)所示的2-氰基丙烯酸酯类化合物外，还可以进一步地含有农业上可接受的载体。
载体可以是固体或液体。合适的固体载体包括天然的或合成的粘土和硅酸盐，例如天然硅石和硅藻土；硅酸镁例如滑石；硅酸铝镁例如高岭石、高岭土、蒙脱土和云母；白碳黑、碳酸钙、轻质碳酸钙；硫酸钙；石灰石；硫酸钠；胺盐如硫酸铵、六甲撑二胺。液体载体包括水和有机溶剂，当用水做溶剂或稀释剂时，有机溶剂也能用做辅助剂或防冻添加剂。合适的有机溶剂包括芳烃例如苯、二甲苯、甲苯等；氯代烃，例如氯代苯、氯乙烯、三氯甲烷、二氯甲烷等；脂肪烃，例如石油馏分、环己烷、轻质矿物油；醇类，例如异丙醇、丁醇、乙二醇、丙三醇和环己醇等；以及它们的醚和酯；还有酮类，例如丙酮、环己酮以及二甲基甲酰胺和N-甲基-吡咯烷酮。
载体也可以是表面活性剂。合适的表面活性剂可以是乳化剂、分散剂或湿润剂；可以是离子型的或非离子型的。非离子型乳化剂例如聚氧乙烯脂肪酸脂、聚氧乙烯脂肪醇醚、聚氧乙烯脂肪氨，以及市售的乳化剂：农乳2201B、农乳0203B、农乳100#、农乳500#、农乳600#、农乳600-2#、农乳1601、农乳2201、农乳NP-10、农乳NP-15、农乳507#、农乳OX-635、农乳OX-622、农乳OX-653、农乳OX-667、宁乳36#。分散剂包括木质素磺酸钠、拉开粉、木质素磺酸钙、甲基萘磺酸甲醛缩合物等。湿润剂为：月桂醇硫酸钠、十二烷基苯磺酸钠、烷基萘磺酸钠等。
本发明还提供一种杀菌方法，所述方法包括：将通式(I)所示的2-氰基丙烯酸酯类化合物施用于需要控制的病菌或其生长的介质上。当将通式(I)所示的2-氰基丙烯酸酯类化合物施用于需要控制的病菌或其生长的介质上时，其施用量为每公顷10～1000克。
具体实施方式
下面结合具体实施例来对本发明进行进一步说明，但并不将本发明局限于这些具体实施方式。本领域技术人员应该认识到，本发明涵盖了权利要求书范围内所可能包括的所有备选方案、改进方案和等效方案。
一、化合物制备
实施例1：化合物20和124的合成
步骤1：中间体20a的合成
将1.09g 4,6-二氯-1-茚酮和0.74g氰乙酸乙酯、20mL二氯甲烷加入反应瓶中，冰浴下缓慢滴加2.08g四氯化钛，滴加结束后搅拌30分钟。冰浴下继续滴加0.3mL吡啶，滴加结束后升至室温并搅拌1小时，然后再加入0.9mL吡啶，室温搅拌12小时。反应结束后，用3M盐酸水溶液淬灭反应，分出有机相，水相再用二氯甲烷萃取两次。合并有机相，经无水Na2SO4干燥后浓缩，得到0.91g含有Z式和E式构型的混合物20a(褐色固体，收率56.5％)，该粗品未经进一步纯化直接投入下一步反应。
步骤2：化合物20和124的合成
零下30℃下，将5.35g二氯化二硫缓慢滴入含有1.30g中间体20a、2.84g N,N-二异丙基乙胺的四氢呋喃溶液中。滴加结束后升温至0℃，并搅拌24小时。向反应液中加入含有2.94g N-氯代丁二酰亚胺的四氢呋喃溶液，并加热回流5小时。反应结束后，过滤，滤液浓缩后用柱色谱分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：20)，分别得到0.50g Z式构型的化合物20(红色固体，收率31.3％)和0.20g E式构型的化合物124(红色固体，收率12.8％)。
实施例2：化合物24和128的合成
步骤1：中间体24a的合成
将0.72g 1-茚酮和0.74g氰乙酸乙酯、20mL二氯甲烷加入反应瓶中，冰浴下缓慢滴加2.08g四氯化钛，滴加结束后搅拌30分钟。冰浴下继续滴加0.3mL吡啶，滴加结束后升至室温并搅拌1小时，然后再加入0.9mL吡啶，室温搅拌12小时。反应结束后，用3M盐酸水溶液淬灭反应，分出有机相，水相再用二氯甲烷萃取两次。合并有机相，经无水Na2SO4干燥后浓缩，得到1.01g含有Z式和E式构型的混合物24a(褐色固体，收率91.4％)，该粗品未经进一步纯化直接投入下一步反应。
步骤2：化合物24和128的合成
将0.50g中间体24a、2.35g N-溴代丁二酰亚胺、0.49g三乙烯二胺、50mL四氢呋喃加入反应瓶中，室温搅拌24小时。反应结束后，加入10％的硫酸水溶液，并用二氯甲烷萃取两次。合并有机相，经无水Na2SO4干燥后浓缩，再用柱色谱分离(洗脱剂为乙酸乙酯与石油醚，体积比为1：20)，分别得到0.24g Z式构型的化合物24(红色固体，收率28.8％)和0.09gE式构型的化合物128(红色固体，收率10.9％)。
二、制剂制备
以下实施例3至实施例7给出以本发明的化合物(I)作为活性物质组份，加工配制几种杀菌剂剂型的实际例子，需要指出的是本发明并不仅仅局限在下述实例的范围内。在这些配方例子中，所有的“％”均指重量百分比。
实施例3、可湿性粉剂配方
将15％的化合物(I)(索引表1和索引表2)、5％的木质素磺酸盐(Mq)、1％的月桂醇聚氧乙烯醚(JFC)、40％的硅藻土和44％的轻质碳酸钙均匀地混合，粉碎，即得可湿性粉剂。
实施例4、乳油配方
将10％的化合物(I)(索引表1和索引表2)、5％的农乳500号(钙盐)、5％的农乳602号、5％的N-甲基-2-吡咯烷酮和75％的二甲苯加热搅拌均匀，即得乳油。
实施例5、粒剂配方
将5％的化合物(I)(索引表1和索引表2)、1％的聚乙烯醇(PVA)、4％的萘磺酸钠甲醛缩合物(NMO)和90％粘土均匀地混合，粉碎，然后向此100份混合物加入20份水，捏合，用挤压成粒机，制成14－32目的颗粒，干燥，即得颗粒剂。
实施例6、水分散性颗粒剂配方
将20％的化合物(I)(索引表1和索引表2)、萘磺酸盐甲醛缩合物4％、萘磺酸盐1％、白炭黑2％和73％高岭土进行混合粉碎，再加水捏合后，加入装有一定规格筛网的造粒机中进行造粒。然后再经干燥、筛分(按筛网范围)即得颗粒状产品。
实施例7、水悬浮剂配方
将20％的化合物(I)(索引表1和索引表2)、脂肪醇聚氧乙烯醚1％、松香嵌段聚氧乙烯醚聚氧丙烯醚磺酸盐3％、硅酸镁铝1％、有机硅消泡剂0.4％、丙二醇5％和去离子水(69.5％)进行预先混合均匀，再加入砂磨机中砂磨，过滤后得到悬浮母液，加入配置好的黄原胶(0.1％)水溶液剪切混合均匀即可。
三、活性测试
下面给出使用本发明的化合物进行生物活性测定的实例，需要指出的是本发明并不仅仅局限在下述实例的范围内。
实施例8、室内活性测定试验
采用孢子萌发法测定化合物对真菌的抑制活性。将试验病原菌置于PDA平板上，培养3天，然后在新鲜菌落边缘用打孔器打取5个直径0.5cm的菌块接种到装有30mL CMC(15gcarboxylmethyl cellulose,1g yeast extract,0.5g MgSO4,1g NH4NO3,1g KH2PO4 and1L water)培养液的50ml三角瓶中25℃，180rpm光照摇培4天诱导产生孢子。用三层擦净纸过滤孢子，制备孢子悬浮液。将分生孢子(终浓度为104/mL)添加到装有2％蔗糖溶液的24孔(每孔2.0毫升)的培养皿中，待测化合物用DMSO溶解，然后用DMSO将待测化合物分别稀释到所测试的浓度。然后将不同浓度的待测化合物加入24孔培养皿中，测试它们对分生孢子萌发的活性。25℃静置培养3h后，在显微镜下用血球计数器统计各孔中萌发的分生孢子数，用公式MGIR％＝[(C-N)/C]×100计算孢子萌发抑制率(MGIR)，其中C为未处理对照组孢子萌发数，N为处理组孢子萌发数。计算各处理的分生孢子萌发率。每个实验重复三次。试验病原菌为小麦赤霉病原菌、黄瓜灰霉病原菌、水稻纹枯病原病和炭疽病原菌。
本发明对索引表1和索引表2中所述编号化合物进行离体杀菌活性评价并将氰烯菌酯作为对照药剂，结果表明：本发明化合物具有良好的杀菌活性，特别是对赤霉病原菌具有很好的杀菌活性，“mg/L”均指每毫克活性物/升，具体如下：
在2.0mg/L浓度下，化合物1、12、15、24、70、93、94、96、101、102、103、104、105、116、119、128、174、197、198、200、205、206、207、208对赤霉病原菌的的孢子萌发的抑制率大于90％，对照药剂氰烯菌酯(2.0mg/L)对赤霉病原菌的的孢子萌发的抑制率为76％；
在1.0mg/L浓度下，化合物1、15、24、93、94、101、102、104、105、119、197、205、206、208对赤霉病原菌的的孢子萌发的抑制率大于90％，对照药剂氰烯菌酯(1.0mg/L)对赤霉病原菌的的孢子萌发的抑制率为46％。
实施例9、小麦赤霉病田间药效试验
在江苏省海安市对待测化合物进行了小麦赤霉病的田间防效试验，所测小麦品种为Jimai 22。田间试验采用随机的小区设计，每个处理重复三次。每个地块的面积为5×10平方米。在小麦抽穗杨花期(15％)喷洒禾谷镰刀菌分生孢子悬液(104/mL)。接种2天后，喷洒待测化合物(5％乳油)或对照药剂氰烯菌酯(25％悬浮剂)。接种40天后，统计每个小区的小麦赤霉病病情指数(Disease index，DI)。小麦病情指数按照5个等级来进行评估，分类等级编号为0到4，对应一株小麦的发病程度的百分比(0＝0；1＝1-25；2＝26-50；3＝51-75；4＝>75％)。用公式[(Σ每个点的小麦数量×评价等级)/(总数小麦×4)]×100％计算各个处理的病情指数。采用Abbott公式[(阴性对照的DI-处理的DI)/阴性对照的DI)]×100％计算各个处理的防效，具体结果见表4。
表4小麦赤霉病田间药效试验结果
| 试验药剂 | 剂量(g/ha) | 田间防效％ |
| 化合物1 | 375 | 45.7±0.75 |
| 化合物24 | 375 | 42.5±1.05 |
| 化合物101 | 375 | 85.3±0.97 |
| 化合物104 | 375 | 62.6±0.82 |
| 氰烯菌酯 | 375 | 60.3±1.28 |
Claims (7)
1.一种通式(I)所示的2-氰基丙烯酸酯类化合物的应用，其特征在于：所述2-氰基丙烯酸酯类化合物用于防治真菌病害，所述防治真菌病害为防治赤霉病、稻瘟病、灰霉病、炭疽病、恶苗病、霜霉病和白粉病中的至少一种病害；
所述2-氰基丙烯酸酯类化合物如下通式(I)所示：
其中：
X1、X3、X4选自氢；X2选自氢、氯或甲基；Y1选自氟、氯或溴；Y2选自氢、氯或溴；R选自甲基、乙基、乙氧基乙基或四氢-2-呋喃基；
所述应用不包括人体/动物疾病的诊断和治疗。
2.根据权利要求1所述的2-氰基丙烯酸酯类化合物的应用，其特征在于：所述2-氰基丙烯酸酯类化合物为顺式结构或反式结构。
3.根据权利要求1所述的2-氰基丙烯酸酯类化合物的应用，其特征在于：所述2-氰基丙烯酸酯类化合物选自以下化合物中的至少一种：
4.根据权利要求1所述的2-氰基丙烯酸酯类化合物的应用，其特征在于：所述2-氰基丙烯酸酯类化合物的制备方法包括：
其中，所述催化剂选自四氯化钛、三氯化铝、三氟化硼、二氯化锌、三氯化铁、三溴化铁或四氯化锡中的至少一种；
所述卤代试剂选自氯气、三氯化磷、二氯化二硫、N-氯代丁二酰亚胺、溴素、氢溴酸、N-溴代丁二酰亚胺、二溴海因、氟化钾、N-氟代双苯磺酰胺或选择性氟试剂中的至少一种；
所述碱选自4-二甲氨基吡啶、吡啶、哌啶、N,N-二异丙基乙基胺、二乙胺、三乙胺和三乙烯二胺中的至少一种；
所述溶剂选自二氯甲烷、三氯甲烷、甲苯、苯、乙腈、丙酮、N,N-二甲基甲酰胺、四氢呋喃和二氧六环中的至少一种。
5.一种农药制剂，其特征在于：所述农药制剂含有0.001％-99.99％重量百分比的权利要求1-3任一所述通式(I)所示的2-氰基丙烯酸酯类化合物。
6.一种杀菌方法，其特征在于：将权利要求1-3任一所述通式(I)所示的2-氰基丙烯酸酯类化合物施用于需要控制的病菌或其生长的介质上，所述病菌为赤霉病原菌、稻瘟病原菌、灰霉病原菌、炭疽病原菌、恶苗病原菌、霜霉病原菌和白粉病原菌中的至少一种，所述杀菌方法不包括人体/动物疾病的诊断和治疗。
7.按照权利要求6所述的杀菌方法，其特征在于：所述2-氰基丙烯酸酯类化合物的施用量为每公顷10～1000克。
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Denomination of invention: A 2-cyanoacrylate compound, its preparation method and application Granted publication date: 20230919 Pledgee: Industrial and Commercial Bank of China Limited Hangzhou Zhaohui sub branch Pledgor: SINOCHEM LANTIAN Co.,Ltd. Registration number: Y2024330001056 |