CN114560825A - 一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法及应用 - Google Patents
一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法及应用 Download PDFInfo
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Abstract
本发明公开了一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法及应用。这种用于水稻二化螟防治的苯并异噻唑类化合物的合成方法简单，用这种苯并异噻唑类化合物制备的杀虫剂能解决二化螟的抗药性，同时可降低防治成本和减轻对环境的污染，在用于水稻二化螟防治的防治中具有很好的前景。
Description
技术领域
本发明涉及农用杀虫剂技术，具体一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法及应用。
背景技术
水稻是我国三大粮食作物之一，目前种植面积已居世界第二位，产量占全球32％左右，全国65％以上人口以稻米为主食，生产的85％以上稻米作为口粮消费，为保障中国粮食安全做出了巨大贡献。所以，提高水稻的单产、总产对保证粮食安全有举足轻重的意义。农作物有害生物治理是农业生产重要环节之一，是农业科技工作者关注的重点课题。随着对有害生物化学物防治的一年又一年的延续、农药使用量的增加以及不科学使用农药等因素的影响，导致病虫害抗性日益严重，产生抗性的害虫、病菌种类不断增多。同时，由于高强度地使用农药，引起农产品农药残留超标、污染环境等一系列社会问题，不利于农业的可持续发展。
水稻二化螟(Chilo surpressalis(Walker))属鳞翅目螟蛾科，常被称作蛀干虫、钻心虫，是我国水稻产业危害最严重、最常见的害虫之一。自20世纪80年代以来，随着杂交稻种植面积不断扩大等耕种形式的变化，二化螟表现出危害加重的趋势，已逐渐上升为稻螟的优势种群，二化螟虫对水稻生长各个时期均有危害，以秧苗分蘖期和出穗期危害最为明显，影响时间长达5个月，可影响3～4代水稻的种植。二化螟是目前水稻上最重要害虫之一,随着我国水稻大面积种植、秸秆禁止焚烧、轻减栽培的推广,二化螟种群数量将迎来爆发。目前化学防治依然是当前田间防治二化螟的主要措施,常用药剂有阿维菌素、甲胺基阿维菌素苯甲酸盐、杀虫单、氯虫苯甲酰胺、氟苯虫酰胺、乙基多杀菌素、甲氧虫酰肼等,而长期不合理用药会导致二化螟抗药性上升、防效下降,对水稻产量和品质造成很大影响。
发明内容
本发明的目的是针对现有技术的不足，而提供一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法及应用。这种用于水稻二化螟防治的苯并异噻唑类化合物的合成方法简单，用这种苯并异噻唑类化合物制备的杀虫剂能解决二化螟的抗药性，同时可降低防治成本和减轻对环境的污染，在用于水稻二化螟防治的防治中具有很好的前景。
实现本发明目的的技术方案是：
一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法，所述苯并异噻唑类化合物结构式如下所示:
苯并异噻唑类化合物理化性质为:熔点193-194℃、外观为白色晶体，核磁数据及质谱数据如为：
1H NMR(600MHz,Chloroform-d)δ＝10.70(s,1H),8.11(dt,J＝8.0,1.0,1H),7.76-7.70(m,1H),7.63(dt,J＝8.2,0.9,1H),7.55(d,J＝1.1,2H),7.48-7.41(m,1H)；13CNMR(151MHz,Chloroform-d)δ＝165.63,148.45,148.19,148.18,141.04,134.43,132.97,127.65,126.15,124.97,124.91,124.41,124.20,121.03,120.58,119.31；HRMS(ESI)calcdfor C15H8Br2F3N2O3S+m/z[M+H]+：512.8549，found 512.8548。
用于水稻二化螟防治的苯并异噻唑类化合物的制备方法为：
1)将固体三光气和二氯甲烷搅拌溶解，冰水浴；
2)在步骤1)得到的混合液中滴加3,5-二溴-4-氨基三氟甲氧基苯和二氯甲烷的混合液，搅拌均匀；
3)在步骤2)混合液降温后滴入三乙胺和二氯甲烷混合液物，随后升至室温反应完；
4)在步骤3)得到的混合液中再滴加苯并异噻唑-3-酮和四氢呋喃溶液，并加热至45℃-55℃进行回流反应，反应完毕后真空浓缩得黄色固体粗品；
5)往黄色固体粗品中加入洗涤液洗涤，最后得到目标物白色苯并异噻唑类化合物，所述洗涤液为V丙酮/V水＝1:1(体积比)。
一种用于水稻二化螟防治的苯并异噻唑类化合物杀虫剂制备：准确称取的原药即白色苯并异噻唑类化合物，用二甲基亚砜溶解配制成45％-50％母液，然后用含0.1％Trition X-100的去离子水按等比方法将母液稀释成0.1mg/L-0.5mg/L的药液备用，备用药液与水充分混匀、在24小时内施用，如果备用药液即杀虫剂和水没有充分混匀就会显著降低杀二化螟效果。
所述苯并异噻唑类化合物作为杀虫剂的用途，它可以根据需要按照常规方法制成不同的剂型，如液体、乳油或微乳液。
这种用于水稻二化螟防治的苯并异噻唑类化合物的合成方法简单，用这种苯并异噻唑类化合物制备的杀虫剂能解决二化螟的抗药性，同时可降低防治成本和减轻对环境的污染，在用于水稻二化螟防治的防治中具有很好的前景。
具体实施方式
下面结合实施例对本发明的内容作进一步的阐述，但不是对本发明的限定。
实施例：
一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法为：
1)将固体三光气和二氯甲烷搅拌溶解，冰水浴；
2)在步骤1)得到的混合液中滴加3,5-二溴-4-氨基三氟甲氧基苯和二氯甲烷的混合液，搅拌均匀；
3)在步骤2)混合液降温后滴入三乙胺和二氯甲烷混合液物，随后升至室温反应完；
4)在步骤3)得到的混合液中再滴加苯并异噻唑-3-酮和四氢呋喃溶液，并加热至45℃-55℃进行回流反应，反应完毕后真空浓缩得黄色固体粗品；
5)往黄色固体粗品中加入洗涤液洗涤，最后得到目标物白色苯并异噻唑类化合物，所述洗涤液为V丙酮/V水＝1:1(体积比)。
一种用于水稻二化螟防治的苯并异噻唑类化合物杀虫剂制备：准确称取1.00克的原药，用二甲基亚砜溶解配制成50％的母液，然后用含0.1％Trition X-100的去离子水按等比方法将母液稀释成0.1mg/L浓度的药液备用，然后使用喷雾剂均匀喷洒到目标作物上即可。
本例的杀虫剂用来防治水稻二化螟。
试验1：苯并异噻唑类化合物杀虫剂对水稻二化螟的防治试验。
1.试验材料与方法：
1-1)供试虫源：二化螟室内人工饲养种群，当幼虫饲养至3龄时用于生测；
1-2)供试药剂：96％供试样品原药、92％阿维菌素原药来自江西正邦作物保护有限公司；
1-3)人工饲料浸药法：
1-3-1)药液配制：准确称取1.00g的原药，用二甲基亚砜溶解配制成50％的母液，然后用含0.1％Trition X-100的去离子水按等比方法将母液稀释成0.1mg/L浓度的药液备用，配制含0.1％Trition X-100的去离子水的阿维菌素的0.1mg/L浓度，同时以含0.1％Trition X-100的去离子水为对照；
1-3-2)混药饲料配制：按中国专利公开号为CN107167583A的一种检测二化螟抗药性的方法中的方法制备人工饲料，将制备的人工饲料切成长度1.5cm×宽度1.5cm×厚度1.2mm的薄片，把薄片挑入至0.1mg/L浓度药液中浸泡10s后捞出，置于与水平面呈45度的不锈钢丝网面上晾干30min，吸去多余药液后，将带药的人工饲料薄片挑入到直径20cm高9cm的平底玻璃管中，30片薄片/玻璃管；
1-3-3)药剂处理：将3龄敏感二化螟幼虫挑入至1.3.2中含带药人工饲料的玻璃管中，在0.1mg/L浓度处理120头，3次重复，共计360头，药剂处理后12h、24h、48h、72h、96h检查各浓度处理的幼虫死亡数率，幼虫死亡标准：以尖锐镊子轻触虫体，不能正常爬行者视作为死亡个体，计算公式如下：
表1药剂对水稻二化螟药效试验结果
2.结果与分析：如表1所示，试验结果表明：药后12h，苯并异噻唑类杀虫剂显示了更优良的杀虫速效性；药后48h，在供试药剂0.1mg/L的浓度下二化螟的死亡率为56.7％，而阿维菌素0.1mg/L浓度下二化螟的死亡率65％，72h、96h的结果与48小时的结果差异不大，可见供试药剂对水稻二化螟有一定防治效果，作为杀虫剂应用的潜力较大。
Claims (3)
1.一种用于水稻二化螟防治的苯并异噻唑类化合物的制备方法，其特征在于，所述苯并异噻唑类化合物结构式如下所示:
2.根据权利要求1所述的用于水稻二化螟防治的苯并异噻唑类化合物的制备方法，其特征在于，所述方法为：
1)将固体三光气和二氯甲烷搅拌溶解，冰水浴；
2)在步骤1)得到的混合液中滴加3,5-二溴-4-氨基三氟甲氧基苯和二氯甲烷的混合液，搅拌均匀；
3)在步骤2)混合液降温后滴入三乙胺和二氯甲烷混合液物，随后升至室温反应完；
4)在步骤3)得到的混合液中再滴加苯并异噻唑-3-酮和四氢呋喃溶液，并加热至45℃-55℃进行回流反应，反应完毕后真空浓缩得黄色固体粗品；
5)往黄色固体粗品中加入洗涤液洗涤，最后得到目标物白色苯并异噻唑类化合物，所述洗涤液为V丙酮/V水＝1:1(体积比)。
3.一种用于水稻二化螟防治的苯并异噻唑类化合物杀虫剂，其特征在于，所述水稻二化螟防治的苯并异噻唑类化合物杀虫剂的制备为：准确称取的原药即白色苯并异噻唑类化合物，用二甲基亚砜溶解配制成45％-50％母液，然后用含0.1％Trition X-100的去离子水按等比方法将母液稀释成0.1mg/L-0.5mg/L的药液备用，备用药液与水充分混匀、在24小时内施用。
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517022A (en) * | 1967-10-03 | 1970-06-23 | Rohm & Haas | Certain 2-carbamoyl-1,2-benzisothiazolones |
| US20060287375A1 (en) * | 2003-08-26 | 2006-12-21 | Kumiai Chemical Industry Co., Ltd. | Benzisothiazoline derivative, plant disease control agent for agricultural or horticultural use, and pest control agent for agricultural or horticultural use |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3517022A (en) * | 1967-10-03 | 1970-06-23 | Rohm & Haas | Certain 2-carbamoyl-1,2-benzisothiazolones |
| US20060287375A1 (en) * | 2003-08-26 | 2006-12-21 | Kumiai Chemical Industry Co., Ltd. | Benzisothiazoline derivative, plant disease control agent for agricultural or horticultural use, and pest control agent for agricultural or horticultural use |
Non-Patent Citations (1)
| Title |
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| 魏婕等: "苯并异噻唑啉酮甲酰胺类衍生物的合成及海洋防污性能研究" * |
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