CN114644596A - 一种含氟嘧啶芳胺类化合物及其用途 - Google Patents
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Abstract
本发明提供了一种含氟嘧啶芳胺类化合物及其用途，结构如式Ⅰ所示：
Description
技术领域 本发明属于农药中杀虫剂的领域，涉及一种含氟嘧啶芳胺杀虫剂及其用于农业或林业的害虫的防治。
背景技术 农业上害虫危害农作物的生长，导致减产及品质下降。目前对害虫的防治主要依赖化学农药，由于大量频繁使用杀虫剂，害虫对其均产生了严重的抗药性，导致用药量越来越大，防效越来越低，持效期缩短，农残升高等一系列问题。新的不同作用机制的杀虫剂的开发及应用，是解决有害生物抗性的有效手段。文献[吴宁捷,龙程,等.新型4-芳氨基嘧啶类衍生物的合成及其杀虫活性[J].有机化学,2019(39):852-856.]报道了一类4-芳氨基嘧啶类衍生物，经生物活性测试表明，在质量浓度500mg/L时，该系列化合物对粘虫(Mythimna separata)的致死率为100％；且在质量浓度降至为20mg/L时，化合物2-甲基-4-[N-(2-氯-4-氟苯基)氨基]-5-[2-三氟甲基-4-(苯氧基)苯基]-6-甲基嘧啶对粘虫和小菜蛾的致死率分别为80％和60％。
在现有技术中，本发明所述的含氟嘧啶芳胺类化合物(式I)未见公开。
发明内容 本发明的目的在于提供一种结构新颖，合成方法简便、安全高效的杀虫剂，它可用于农业或林业害虫的防治。
本发明的技术方案如下：
一种含氟嘧啶芳胺类化合物及其用途，结构如式Ⅰ所示：
本发明式Ⅰ化合物可由如下反应路线制备：
式Ⅱ化合物与式Ⅲ化合物在乙腈中以三乙胺为催化剂，在室温下进行取代反应，制得式Ⅰ化合物。具体制备方法见本发明实施例。
本发明的优点和积极效果：
本发明化合物作为农业杀虫剂，具有结构新颖、制备简便、且有一定的杀菌作用的优点。本发明化合物对小菜蛾有优异的抑杀效果，可以达到对农林业害虫的优异效果。与商品化杀虫剂唑虫酰胺相比，对小菜蛾的杀灭活性Ⅰ化合物略超过唑虫酰胺，在10mg/L这样的极低浓度下，对小菜蛾的杀灭率也达97％。本发明化合物为含氟氮杂环类化合物，具有生物活性高、对有益生物低毒性、易降解、环境相容性好的特点，特别适用于目前普遍存在的抗药性农业害虫的治理，作为杀虫优异兼具杀菌作用的农药新品种具有很好的开发及应用前景。
本发明化合物在防治农业害虫可单独使用，也可与其它活性物质组合使用，以提高产品的综合性能。
本发明还包括以式Ⅰ化合物为活性组分的杀虫剂组合物，其中活性组分在组合物的重量百分含量为1～99％。该杀虫剂组合物还包括农业或林业上可接受的载体。
应该明确的是，在本发明的权利要求的限定范围内，可进行各种变动或改动。
具体实施方式
下列合成实例、生测试验结果可用来进一步说明本发明，但不意味着限制本发明。
合成实例
实例1、化合物Ⅰ的制备：
(1)中间体式Ⅱ化合物的合成：
在250mL三口反应瓶中，将2-巯基-4-羟基-6-三氟甲基嘧啶19.62g(0.10mol)和碳酸钾16.59g(0.12mol)加入50mL DMF中，室温下搅拌10min后，滴加正溴丁烷15.07g(0.11mol)，滴加完毕后室温反应3h，TLC监测至反应完全，将反应液倒入150mL水中，搅拌下滴加盐酸调至中性，析出固体。抽滤，洗涤，收集滤饼并烘干，得到化合物2-正丁硫基-4-羟基-6-三氟甲基嘧啶，收率87％。
在250mL三口烧瓶中，将2-(正丁硫基)-4-羟基-6-三氟甲基嘧啶25.5g(0.1mol)加入到100mL氯化亚砜中，搅拌，加催化量DMF，加热至回流，反应3h小时，TLC检测至反应完全，减压蒸馏脱去剩余的氯化亚砜。不经纯化直接进行下一步反应。
(2)化合物Ⅰ的合成：
在100mL三口烧瓶中，将式Ⅱ化合物2.71g(10.0mmol)和三乙胺1.21g(12.0mmol)加入20mL乙腈中，室温搅拌0.5h，分批加入2,5-二氯-4-(1,1,2,3,3,3-六氟丙氧基)苯胺3.43g(10.5mmol)，保持室温继续反应3～5h，TLC检测至反应完全。将反应液加入到60mL水中，搅拌，析出固体粗品，粗品经柱层析(V(乙酸乙酯):V(石油醚)＝1:10)分离，得到目标化合物Ⅰ，收率为71％。白色固体，m.p.85.7～87℃。
本发明式Ⅰ的化合物核磁数据如下：
1H NMR(500MHz,DMSO-d6)δ9.98(s,1H),8.19(s,1H),7.70(s,1H),7.05(s,1H),6.51(d,J＝41.3Hz,1H),2.91(t,J＝7.5Hz,2H),1.52–1.44(m,2H),1.26–1.19(m,2H),0.76(t,J＝7.6Hz,3H).
13C NMR(126MHz,DMSO)δ171.99,160.83,153.40,153.12,152.85,152.57,140.58,134.72,127.66,126.32,125.26,124.52,121.55,119.37,99.24,84.86,84.58,84.31,84.03,83.31,83.03,82.75,82.48,39.95,39.78,39.62,39.45,39.28,39.11,38.95,30.89,29.77,21.28,13.12。
生物活性测试
实例2、杀虫活性测定方法
选择小菜蛾为对象进行杀虫活性试验。对小菜蛾的杀虫活性测试所采用的方法是浸叶法(即由国际杀虫剂抗性行动委员会Insecticide Resistance Action Committee，IRAC所提出的)。具体操作方法为：用直头眼科镊子在提前配置好的药液中将甘蓝叶片浸渍3-5s，然后取出药片，除去多余的药液，每次浸渍1片甘蓝叶片，每个样品做三个平行实验，按照标记顺序将叶片放置于处理纸上。待叶片上的药液晾干后，将其分别放入标记好的10cm长的直型试管中，每个试管内各接种3龄小菜蛾幼虫30头，用纱布盖好管口后放置于标准培养室内。该测试以唑虫酰胺为阳性对照药剂，清水为阴性对照药剂。48h后观察实验结果，判断小菜蛾死亡的标准为：虫体干瘪、变黑、并且用毛笔轻轻触试后无明显反应；判断活虫的标准为：虫体湿润、新鲜、用毛笔清扫并保持动态者。根据调查结果计算死亡率(％)。
死亡率(％)＝[(药剂处理死亡率-空白对照死亡率)/(1-空白对照死亡率)]*100
表1式Ⅰ化合物的杀小菜蛾活性测试结果
测试结果表明，本发明化合物Ⅰ对小菜蛾的杀灭效果略优于唑虫酰胺，在10mg/L超低浓度下，杀灭率也达到了97％。
实例3、杀菌活性测定
测试方法采用真菌生长抑制法，培养基为50μg/mL的马铃薯葡萄琼脂培养基(PDA)。具体操作方法为：在无菌环境下，于待测药剂母液中吸取0.5mL加入培养皿中，另外添加9.5mL的PDA培养基，摇晃均匀，形成50mL的含药平板，然后沿菌丝外缘用打孔器截取直径为4mm的菌盘，再移植到含药平板上，之后将培养皿放入培养箱中，24±1℃下培养72h，观测菌盘直径，计算其相对抑制率，重复处理三次，取平均值。所测试用菌株为：油菜菌核病菌(Sclerotinia sclerotiorum(Lib.)de Bary)、小麦赤霉病菌(Fusarium graminearumschw.)、水稻稻瘟病菌(Pyricularia oryae Cav)、水稻纹枯病菌(Rhizoctonia solani)等。该测试的空白对照为含有丙酮和0.1mL/L的Triton X-100的水溶液。
表2式Ⅰ化合物的杀菌活性测试结果
测试结果表明，本发明化合物在50mg/L浓度下，对油菜菌核病菌、小麦赤霉病菌、水稻稻瘟病菌、水稻纹枯病菌有一定的杀菌作用。
Claims (3)
1.一种含氟嘧啶芳胺类化合物及其用途，结构如式Ⅰ所示：
2.根据权利要求1所述的一种含氟嘧啶芳胺类化合物的用途，其特征在于式I化合物用作农业或林业杀虫剂，对农业害虫有防治效果。
3.一种杀虫组合物，含有权利要求1所述的式Ⅰ化合物为活性组分和农业或林业上可接受的载体。
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87103906A (zh) * | 1986-06-04 | 1988-02-24 | 赫彻斯特股份公司 | 新的嘧啶衍生物的制备和应用 |
| WO1992005158A1 (de) * | 1990-09-19 | 1992-04-02 | Hoechst Aktiengesellschaft | 4-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide |
| US5439911A (en) * | 1992-12-28 | 1995-08-08 | Shionogi & Co., Ltd. | Aminopyrimidine derivatives and their production and use |
| WO2002040473A1 (fr) * | 2000-11-17 | 2002-05-23 | Ishihara Sangyo Kaisha, Ltd. | Composes de pyrimidine ou leurs sels, herbicides contenant ces composes ou ces sels, leur procede d'utilisation dans l'elimination des mauvaises herbes |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87103906A (zh) * | 1986-06-04 | 1988-02-24 | 赫彻斯特股份公司 | 新的嘧啶衍生物的制备和应用 |
| WO1992005158A1 (de) * | 1990-09-19 | 1992-04-02 | Hoechst Aktiengesellschaft | 4-anilino-pyrimidine, verfahren zu ihrer herstellung, sie enthaltene mittel und ihre verwendung als fungizide |
| US5439911A (en) * | 1992-12-28 | 1995-08-08 | Shionogi & Co., Ltd. | Aminopyrimidine derivatives and their production and use |
| WO2002040473A1 (fr) * | 2000-11-17 | 2002-05-23 | Ishihara Sangyo Kaisha, Ltd. | Composes de pyrimidine ou leurs sels, herbicides contenant ces composes ou ces sels, leur procede d'utilisation dans l'elimination des mauvaises herbes |
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