CN108299409A - 一种苯醚噁二唑类杀虫剂 - Google Patents
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Abstract
本发明提供一种苯醚噁二唑类杀虫剂,化学结构如式Ⅰ所示：
Description
技术领域 本发明属于农药杀虫剂领域，具体涉及一种苯醚噁二唑类化合物及其作为农业和林业杀虫剂的用途。
背景技术 农业病虫害是导致作物减产或品质降低的主要原因之一，有机磷类及氨基甲酸酯类等常规农药的大量使用，除存在高残留、高毒等问题外，也使害虫产生了严重的抗药性。因此开发高活性、低毒性的新型作用机制的绿色环保化合物是当今农业杀虫剂的主要发展方向。US5039693公开的化合物(式II)，商品名“唑虫酰胺”，对蓟马、小菜蛾等有很好的防治效果。在现有技术中，如本发明所示的3,5-二取代-1,4-噁二唑类杀虫剂(式I)及其杀虫活性未见公开。
发明内容 本发明的目的是提供一种超高效、长持效、抗性小、毒性低、结构新颖的农用杀虫剂，可用于农业或林业害虫的防治。
本发明的技术方案如下：
一种苯醚噁二唑类化合物，结构如式Ⅰ所示：
式I化合物可由如下反应制备：
具体制备方法见本发明实施例1。
本发明的优点和积极效果：
本发明将噁二唑基团引入“唑虫酰胺”(式II化合物)结构中，并对吡唑环上的取代基进行改造，制备了苯醚和吡唑环3,5-二取代-1,4-噁二唑类化合物，是一种全新结构的新型、广谱、内吸性杀虫剂，其新颖的化学结构赋予其与众不同的作用机理和优越的产品性能，对害虫有非常好的杀虫效果，杀虫活性远高于商品化的杀虫剂“唑虫酰胺”(见生测实例2)。此外作为，本化合物生产过程简单、安全，不使用特殊设备和高温高压。因此，本发明化合物作为农药创制新品种，具有高活性、低抗性、低成本及生产工艺简单等优点，同时也弥补了噁二唑类杀虫剂短缺的问题，对我国抗性害虫的治理具有十分积极的意义，作为高效低毒广谱内吸性杀虫剂具有巨大的商品化潜力。
本发明化合物在防治虫害时，根据实际需要可单独使用，也可与其它活性物质如杀虫、杀螨剂组合使用，以利于提高产品的综合性能。
本发明还包括式Ⅰ化合物作为活性组分的杀虫组合物，该组合物中还包括农业或林业上可接受的载体。
本发明的组合物可以制剂的形式施用，式Ⅰ化合物作为活性组分溶于或分散于载体或溶剂中，添加适当的表面活性剂配制成乳油、水乳剂、微乳剂、悬浮剂等。
应明确的是，在本发明的权利要求的限定的范围内，可进行各种变换和改动。
具体实施方式
下列合成实例及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、式Ⅰ化合物的制备：
(1)化合物V的制备
向250mL三口烧瓶中加入7.65g(0.05mol)化合物IV、150mL乙酸乙酯，搅拌条件下滴加2.3g(0.05mol)乙醇，加热至60℃保温反应2h，TLC检测化合物IV消失。旋蒸除去乙酸乙酯，得化合物V8.5g，收率94％。
(2)化合物VI的制备
向250mL三口烧瓶中加入9.05g(0.05mol)化合物V、150mL乙酸乙酯，在搅拌条件下缓慢滴加8.8g(0.065mol)SO2Cl2，室温反应3h，TLC检测化合物V消失，旋蒸除去乙酸乙酯，得化合物VI10.0g，收率92.6％。
(3)化合物VII的制备
向250mL三口烧瓶中加入10.8g(0.05mol)化合物VI、100mL水、50mL甲醇及3gNaOH，水浴加热至50℃，搅拌条件下反应4h，TLC检测化合物VI消失，将反应液降至室温，向反应液中缓慢滴加盐酸，调pH至5-6，抽滤，将滤饼烘干，得淡黄色固体8.6g，即为化合物VII，收率91.5％。
(4)化合物VIII的制备
向250mL三口烧瓶中加入9.4g(0.05mol)化合物VII、150mL甲苯，搅拌条件下加入7.8g(0.065mol)SOCl2，加毕升温回流反应5h，TLC检测化合物VII消失，旋蒸除去甲苯得化合物VIII9.6g，收率93％。
(5)化合物X的制备
向250mL三口烧瓶中加入10.45g(0.05mol)化合物IX、4.2g(0.06mol)盐酸羟胺、150mL乙醇及6g(0.06mol)三乙胺，搅拌条件下加热至回流，在回流条件下反应5h，TLC检测化合物IX消失。旋蒸除去乙醇，加入200mL水洗涤，抽滤，烘干滤饼得白色固体11.5g，即为化合物X，收率95％。
(6)化合物XI的制备
向250mL三口烧瓶中加入12.1g(0.05mol)化合物X、150mL乙酸乙酯及10g(0.1mol)三乙胺，冰水浴搅拌条件下缓慢滴加10.4g(0.05mol)化合物VIII，反应3h，TLC检测化合物X消失。将反应液加入500mL分液漏斗中并加入200mL水洗涤分液，取乙酸乙酯层，用无水硫酸钠干燥后抽滤，旋蒸滤液得深红色油状粘稠液体，用甲醇重结晶得淡黄色固体15.6g，即为化合物XI，收率75.7％。
(7)化合物I的制备
向250mL三口烧瓶中加入20.6g(0.05mol)化合物XI，150mL甲苯，加热至回流，进行回流脱水，反应4h，TLC检测化合物XI消失，旋蒸除去甲苯后得深红色油状粘稠液体，用甲醇重结晶得淡黄色固体15.0g，即为化合物I，收率76.1％。
式I化合物的表征：1H-NMR(500MHz，DMSO)：δ/ppm 1.334-1.4399(t,3H),2.205-2.224(s,3H),2.84-2.323(s,3H),4.562-4.645(q,2H),6.985-7.042(d,2H),7.084-7.141(d,2H),7.212-7.269(d,2H),8.013-8.069(d,2H)。熔点：75-78℃。
生测实例
实例2、式Ⅰ化合物杀虫活性试验
根据本发明化合物的溶解性，将化合物(式I)用DMSO或丙酮溶解，之后用1‰的吐温-80溶液配置成所需浓度的待测试溶液100mL。
杀甜菜夜蛾活性测定：
将甘蓝叶片用打孔器打出直径为1cm的叶碟，进行喷雾处理，对每个叶碟的正反面进行喷雾，喷雾量0.5mL，待叶片阴干后每个处理的叶碟接入30头试虫(3龄)，每个叶碟进行三次重复性试验。处理后将其放入温度为24℃、相对湿度为60～70％、无光照的室内培养96h，之后调查存活虫数，计算死亡率。每个样品进行3次重复实验，结果取平均值，试验结果见表2。
表2杀甜菜夜蛾活性测试数据
从表2生测结果看出，本发明化合物(式I)较唑虫酰胺(式II)有更高的杀虫活性。
Claims (3)
1.一种苯醚噁二唑类杀虫剂,化学结构如式Ⅰ所示：
2.根据权利要求1所述的一种苯醚噁二唑类杀虫剂的用途，其特征在于式Ⅰ化合物单一使用或与另外的生物活性化合物的组合使用，防治农业或林业虫害。
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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| HONGJIAN SONG,ET AL.: "Design, Synthesis, and Insecticidal Activity of Novel Pyrazole Derivatives Containing α-Hydroxymethyl-N-benzyl Carboxamide, α-Chloromethyl-N-benzyl Carboxamide, and 4,5-Dihydrooxazole Moieties", 《JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY》 * |
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