CN103109816A - 硫代苯甲酰胺类化合物及其应用 - Google Patents
硫代苯甲酰胺类化合物及其应用 Download PDFInfo
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Abstract
本发明公开了一种新型硫代苯甲酰胺类化合物，其结构如通式I所示：
式I中：R1选自Cl或Br；R2选自甲基，异丙基，烯丙基；R3选自H或Cl。通式I化合物具有优异的杀虫活性，可用于农、林常见害虫尤其是抗性害虫的防治。
Description
技术领域
本发明属于农用杀虫剂领域，涉及一种硫代苯甲酰胺类化合物及其应用。
背景技术
由于大量频繁的用药，害虫对现有杀虫剂均产生了不同程度的抗药性，开发新型作用机制的杀虫剂，是治理害虫抗药性的有效手段。随着人们对生活质量及环保要求的提高，研究开发高效安全、绿色环保杀虫剂符合农药发展趋势要求。WO2003/015519公开了如下具有杀虫活性的化合物(KC)。该化合物作为杀虫剂已商品化(商品化名：康宽)，对鳞翅目害虫具有超高效、长持效等特点，但存在溶解性差、可加工剂型少等缺点。
在现有的技术中，如本发明所示的硫代酰胺类化合物的制备及其杀虫活性未见公开。
发明内容
本发明的目的在于提供一种新的害虫防治剂，它可用于农业(或林业)常见害虫的防治。根据生物电子等排理论，本发明化合物不仅继承了原有化合物(如KC)的高活性，且在有机溶剂中有较高的溶解度，特别有利于配制水乳剂、微乳剂等绿色剂型制剂，硫取代氧也有利于降低化合物对有脊柱动物的毒性。因此本发明的化合物更有潜力开发成高效绿色环保杀虫剂。
本发明的技术方案如下：
一种硫代苯甲酰胺类化合物，如通式I所示：
式中：R1选自Cl或Br；
R2选自H，甲基，乙基，异丙基，烯丙基；
R3选自H或Cl。
本发明中进一步优选化合物为，通式I中：
R1选自Cl；
R2选自甲基，异丙基，烯丙基；
R3选自H或Cl。
综合原料来源、合成简便、防治成本低廉及环保等因素，本发明更进一步优选的化合物为：通式I中：
R1选自Cl；
R2选自甲基，烯丙基；
R3选自H或Cl。
本发明的通式I化合物可由如下方法制备，反应式中各基团定义同前。
通式II化合物在适宜的溶剂中，温度为-5℃到回流温度下与化合物III反应1-24h制得通式I化合物，反应过程中可加入缚酸剂提高反应速度，适宜的缚酸剂选自三乙胺、吡啶、甲基吡啶或碳酸钠、碳酸钾等；反应过程适宜的溶剂选自乙酸乙酯、乙腈、苯、甲苯、THF、二氧六环或DMF等；通式III化合物可以参考US2006/079561A1、WO2009/085816A1或CN101333213A中的方法制备。表1列出了部分通式I化合物的结构和物理性质。
表1部分通式I化合物的结构和物理性质
| 化合物 | R1 | R2 | R3 | 外观(熔点℃) |
| 1 | Cl | CH3 | H | 淡黄色(178～181) |
| 2 | Cl | CH(CH3)2 | H | 淡黄色(167～171) |
| 3 | Cl | CH2CH＝CH2 | H | 淡黄色(162～165) |
| 4 | Br | CH3 | Cl | 白色(172～175) |
| 5 | Br | CH2CH＝CH2 | H | 淡黄色(171～173) |
| 6 | Cl | CH3 | Cl | 白色(161～164) |
| 7 | Cl | CH(CH3)2 | Cl | 白色(156～159) |
| 8 | Cl | CH2CH＝CH2 | Cl | 白色(148～151) |
本发明的优点和积极效果：与已知的苯甲酰胺类化合物(如KC)相比，本发明的硫代苯甲酰胺类化合物不仅对鳞翅目害虫具有高活性，且对刺吸式害虫(如稻飞虱)亦有意想不到的高活性，因此具有更好的兼治作用及综合功能。本发明的硫代苯甲酰胺类化合物进入无脊椎的害虫体内，硫原子迅速被氧化成氧原子而发挥毒杀作用，但这个过程在有脊椎的高等动物体内进行很缓慢，故硫原子取代氧原子有利于降低化合物对人畜及环境的影响，因而更安全环保。且硫原子取代氧原子后所制得的本发明化合物在常见有机溶剂中(如乙腈、二氯甲 烷等)有较好的溶解性，克服了已知化合物(如KC)难溶性的弊端，既可制成悬浮剂，也可制成水乳剂、微乳剂等绿色剂型，从而使有效利用率成倍提高，实现了从有效成分到剂型绿色化的统一。
需要明确的是，本发明的权利要求所限定的范围内，可进行各种变化和改动。
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。
实施例1化合物1的制备
(1)8-甲基-1H-[1，3]-苯并噁嗪-2，4-二酮的合成
向500mL反应瓶中，分别加入15.1g(0.1mol)2-氨基-3-甲基苯甲酸，150mL乙酸乙酯，0.5g吡啶，搅拌下于10℃以下滴加由19.8g(0.067mol)三光气和100mL乙酸乙酯组成的溶液，滴毕，于30-35℃搅拌反应4小时，然后升温回流2小时，去尽光气，冷至室温，抽滤，水洗，得到白色固体15.9g，收率89.8％。
(2)2-氨基-N，3-二甲基苯甲酰胺的合成
向250mL反应瓶依次加入8-甲基-1H-[1，3]-苯并噁嗪-2，4-二酮17.8g(0.1mol)，100mL乙酸乙酯，1.5g冰乙酸，于15-20℃下逐渐加入15.5g(0.2mol)40％的甲胺水溶液，滴毕，室温搅拌2小时，分液，静置分去水层，无水硫酸镁干燥，抽滤，蒸干溶剂，得到白色固体14.1g，收率86％。
(3)2-氨基-5-氯-N，3-二甲基苯甲酰胺的合成
向250mL反应瓶依次加入2-氨基-5-氯-N，3-二甲基苯甲酰胺16.4g(0.1mol)，乙腈80mL，冰浴下滴加SO2Cl216.2g(0.12mol)，滴毕升至室温，搅拌反应4h，加入20％NaHCO3水溶液调pH至中性，抽滤，水洗，得到白色固体17.6g，收率88.6％。
依此法可制得其它R2基团的同类化合物。
(4)2-氨基-5-氯-N，3-二甲基硫代苯甲酰胺的合成
向500mL的四口瓶中，加入P2S522.2g(0.1mol)，Na2CO310.6g(0.1mol)，乙酸乙酯200mL，室温搅拌1h至体系澄清，分批次加入2-氨基-5-氯-N，3-二甲基苯甲酰胺19.85g(0.1mol)，升温至回流5h，待原料反应完全后，降至室温，加入30mL水至体系澄清，分液，乙酸乙酯层用饱和食盐水溶液洗涤(30mL×2)，无水Na2SO4干燥，蒸干溶剂，得到黄色固体17.3g，产率80.65％。
(5)化合物1的合成
向100mL反应瓶中加入2.14g(0.01mol)2-氨基-5-氯-N，3-二甲基硫代苯甲酰胺，20mL乙腈，1.21g(0.012mol)三乙胺，搅拌下于0-10℃滴加由3.53g(0.011mol)1-(3-氯-2-吡啶基)-3-溴-1H-吡唑-5-甲酰氯与10mL乙腈组成的混合溶液，滴毕，室温搅拌3小时，旋蒸出溶剂，加水30mL，用80mL二氯甲烷萃取，有机层用饱和碳酸氢钠溶液和食盐水溶液洗涤，无水硫酸钠干燥后浓缩，残余物柱层析提纯(淋洗剂为乙酸乙酯∶石油醚＝1∶2)得4.4g的淡黄色固体，收率84.1％。1H NMR(500MHz，DMSO-d6)δ(ppm)：2.137(s，3H)，2.888-2.987(d，3H)，7.116(s，1H)，7.311(s，1H)，7.385(s，1H)，7.592-7.618(m，1H)，8.161-8.177(d，1H)，8.487-8.496(d，1H)，10.120(s，1H)，10.257(s，1H)。
实施例2化合物3的制备
(1)2-氨基-3-甲基-5-氯-N-烯丙基硫代苯甲酰胺的合成
向500mL的四口瓶中，加入P2S522.2g(0.1mol)，Na2CO310.6g(0.1mol)，乙酸乙酯200mL，室温搅拌1h至体系澄清，分批次加入22.45g(0.1mol)2-氨基-3-甲基-5-氯-N-烯丙基苯甲酰胺(按实施例1方法制备)，升温至回流6h，待原料反应完全后，降至室温，加入30mL水至体系澄清，分液，乙酸乙酯层用饱和食盐水溶液洗涤(30mL×2)，无水Na2SO4干燥，蒸干溶剂，得到橙黄色固体17.3g，产率71.93％。
(2)化合物3的合成
向100mL反应瓶中加入2.4g(0.01mol)2-氨基-3-甲基-5-氯N-烯丙基硫代苯甲酰胺，20mL乙腈，1.21g(0.012mol)三乙胺，搅拌下于0-10℃滴加由3.53g(0.011mol)1-(3-氯-2-吡啶基)-3-溴-1H-吡唑-5-甲酰氯与10mL乙腈组成的混合溶液，滴毕，室温搅拌3小时，旋蒸出溶剂，加水30mL，用80mL二氯甲烷萃取，有机层用饱和碳酸氢钠溶液和食盐水洗涤，无水硫酸钠干燥后浓缩，残余物柱层析提纯(淋洗剂为乙酸乙酯∶石油醚＝1∶2)，得3.4g淡黄色固体，收率64.8％。1H NMR(500MHz，DMSO-d6)δ(ppm)：2.139(s，3H)，3.801(s，2H)，5.049-5.184(d，2H)，6.227-6.538(m，1H)7.313(s，1H)，7.381(s，1H)，7.588-7.622(m，1H)，7.756(s，1H)，8.151-8.174(d，1H)，8.485-8.516(d，1H)，10.132(s，1H)，10.301(s，1H)。
实施例3化合物7的制备
(1)2-氨基-3-甲基-5-氯-N-异丙基硫代苯甲酰胺的合成
向500mL的四口瓶中，加入P2S522.2g(0.1mol)，Na2CO310.6g(0.1mol)，乙酸乙酯200mL，室温搅拌1h至体系澄清，分批次加入2-氨基-3-甲基-5-氯N-异丙基苯甲酰胺(按实施例1方法制备)22.65g(0.1mol)，升温至回流6h，待原料反应完全后，降至室温，加入30mL水至体系澄清，分液，乙酸乙酯层用饱和食盐水溶液洗涤(30mL×2)，无水Na2SO4干燥，蒸干溶剂，得到黄色固体17.8g，产率73.4％。
(2)化合物7的合成
向100mL反应瓶中加入2.42g(0.01mol)2-氨基-3-甲基-5-氯-N-异丙基硫代苯甲酰胺，20mL乙腈，1.21g(0.012mol)三乙胺，搅拌下于0-10℃滴加由3.91g(0.011mol)1-(3-氯-2-吡啶基)-3-溴-1H-吡唑-5-甲酰氯与10mL乙腈组成的混合溶液，滴毕，室温搅拌3h，旋蒸出溶剂，加水30mL，用80mL二氯甲烷萃取，有机层用饱和碳酸氢钠溶液和食盐水溶液洗涤，无水硫酸钠干燥后浓缩，残余物柱层析提纯(淋洗剂为乙酸乙酯∶石油醚＝1∶2)得 3.62g的白色固体，收率64.5％。1H NMR(500MHz，DMSO-d6)δ(ppm)：1.088(d，6H)，2.137(s，3H)，4.211-4.463(m，1H)，7.218(s，1H)，7.467(s，1H)，7.761(s，1H)，8.148(s，1H)，8.472(s，1H)，10.191-10.207(d，1H)，10.409(s，1H)。
按照以上方法来制备本发明通式I中的其他化合物。通式I部分化合物的1H NMR(500MHz，DMSO-d6)δ(ppm)数据如下：
化合物2：1.074(d，6H)，2.137(s，3H)，4.211-4.463(m，1H)，7.214(s，1H)，7.455(s，1H)，7.587-7.613(m，1H)，7.756(s，1H)，8.142-8.158(d，1H)，8.468-8.477(d，1H)，10.191-10.207(d，1H)，10.409(s，1H)。
化合物4：2.137(s，3H)，2.887-2.977(d，3H)，7.112(s，1H)，7.308(s，1H)，7.365(s，1H)，8.172(s，1H)，8.488(d，1H)，10.186(s，1H)，10.347(s，1H)。
化合物5：2.139(s，3H)，3.811(s，2H)，5.052-5.185(d，2H)，6.217-6.536(m，1H)7.312(s，1H)，7.385(s，1H)，7.577-7.631(m，1H)，7.756(s，1H)8.149-8.174(d，1H)，8.479-8.518(d，1H)，10.135(s，1H)，10.321(s，1H)。
化合物6：2.145(s，3H)，2.788-2.993(d，3H)，7.127(s，1H)，7.305(s，1H)，7.403(s，1H)，8.153(s，1H)，8.467(s，1H)，10.132(s，1H)，10.257(s，1H)。
化合物8：2.142(s，3H)，3.811(s，2H)，5.049-5.182(d，2H)，6.228-6.538(m，1H)7.309(s，1H)，7.367(s，1H)，8.274(s，1H)，8.536(s，1H)，10.147(s，1H)，10.331(s，1H)。
生物活性测定
实施例4杀虫活性测定
杀小菜蛾活性测定：
采用浸叶法。采用国际抗性行动委员会(IRAC)提出的浸叶法。用配制好的待测药液，用直头眼科镊子浸渍甘蓝叶片，时间3-5秒甩掉余液，每次1片，每个样品共3片，按样品标记顺序依次放在处理纸上。待药液干后，放入具有标记的10cm长的直型管内，接入2龄小菜蛾幼虫30头，用纱布盖好管口。将试验处理置于标准处理室内，48h检查结果，以拔针轻触虫体，不动者为死亡。计算死亡率。试验做3次重复，取平均值，实验结果见表2。
表2式I化合物与已知化合物KC杀小菜蛾活性平行比较(死亡率％)
杀稻飞虱活性测定：
采用浸稻芽法：将长10-15cm的水稻幼苗浸入相应处理药液中5秒钟后取出，放在报纸上摊开吸干多余的药液后，植入100mL透明饲养瓶中，用适量润湿细沙固定，减掉长出瓶口 的叶片，再把试虫放到饲养瓶中饲养，于观察室内保温保湿饲养，药后2天分别调查各处理活虫数、死虫数、计算死亡率及校正死亡率。实验结果见表3
表3部分化合物对稻飞虱活性试验结果
| 化合物 | 浓度(ppm) | 校正死亡率(％) |
| 1 | 20 | 78 |
| 2 | 20 | 65 |
| 4 | 20 | 73 |
| 5 | 20 | 42 |
| 9 | 20 | 55 |
| KC | 20 | 34 |
从表2和表3生测结果看出，本发明部分化合物较已知化合物KC有更高的杀小菜蛾和稻飞虱活性。
Claims (3)
1.一种邻氨基硫代苯甲酰胺类杀虫剂，结构如通式I所示：
式I中：R1选自Cl或Br；
R2选自甲基，异丙基，烯丙基；
R3选自H或Cl。
2.一种按照权利要求1所述的通式I化合物控制虫害的用途。
3.一种杀虫组合物，含有权利要求1所述的通式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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