CN105330661A - 一种n-芳甲基取代的噁二嗪硝基亚胺衍生物及其用途 - Google Patents
一种n-芳甲基取代的噁二嗪硝基亚胺衍生物及其用途 Download PDFInfo
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- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
Abstract
本发明公开了一种N-芳甲基取代的噁二嗪硝基亚胺衍生物,结构如式I所示:
Description
技术领域本发明属于农药中杀虫剂领域,涉及一种N-芳甲基取代的噁二嗪硝基亚胺衍生物及其杀虫剂用途。
背景技术噻虫嗪(式Ⅱ化合物)(KC)是诺华公司开发的新型烟碱类高效低毒杀虫剂,对害虫具有胃毒、触杀及内吸活性,对鞘翅目、双翅目、鳞翅目,尤其是同翅目害虫有高活性,可有效防治各种蚜虫、叶蝉、飞虱类、粉虱、金龟子幼虫、马铃薯甲虫、线虫、地面甲虫、潜叶蛾等害虫及对多种类型化学农药产生抗性的害虫,与吡虫啉、啶虫脒、烯啶虫胺无交互抗性,既可用于茎叶处理、种子处理、也可用于土壤处理,已成为目前水稻、甜菜、油菜、马铃薯、花生、大豆、棉花等农作物和果树害虫防治的常规农药品种。噁二嗪环N上烷基取代基部分对不同害虫药效有影响(程霞编译,亦冰校,第二代新烟碱类杀虫剂噻虫嗪的开发,世界农药,2001,23(4):17-25),因此本发明在噻虫嗪的基础上设计合成了式Ⅰ化合物,出乎意料地提高了对蚜虫、飞虱类害虫的药效,增加了防效。在现有技术中,如本发明所示的式Ⅰ化合物用作杀虫剂未见公开。
发明内容本发明的目的是提供一种N-芳甲基取代的噁二嗪硝基亚胺衍生物杀虫剂,可用于农业或林业有害虫的防治。
本发明的技术方案如下:
一种N-芳甲基取代的噁二嗪硝基亚胺衍生物杀虫剂,结构如式I所示:
根据需要,式I化合物作为杀虫组分用于杀虫单剂或复合制剂,其适宜剂型为乳油、水分散粒剂、悬浮剂及可湿性粉剂等。
式I化合物的制备见本发明合成实例。
本发明的优点和积极效果:
蚜虫、蓟马、飞虱类等吸收式口器害虫,通过昆虫口器刺吸植物幼嫩组织,吸食组织中的汁液。根据现代农业对低公害、超高效、长持效药剂的要求,防治这类害虫的药剂必须具有较强的内吸传导功能,这是提高防治效果和延长持效期的基础。本发明人首次将具有亲水亲油双亲作用的呋喃基引入噻虫嗪母体结构中,显著提高了其内吸传导作用,大幅度延长了防治稻飞虱的持效期(见表2),这对减少施药次数、降低防治费用、减少环境污染、省时省工等具有十分重要的意义。本发明化合物毒性低、用药量小,符合现代农业对低公害、超高效、长持效的要求,具有创制商品化杀虫剂的潜力。
本发明式I化合物及其盐在防治有害虫时,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。
应该明确的是,在本发明的权利要求所限定的范围内,可进行各种变换和改动。
具体实施方式
下列合成实例、制剂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
实施例1、3-(2-氯-1,3-噻唑-5-基甲基)-5-呋喃甲基-1,3,5-噁二嗪-4-基叉(硝基)胺的制备:
(1)化合物1-呋喃甲基-3-硝基胍的合成:
合成反应式:
在250mL三口烧瓶中,加入10.40g(0.10mol)硝基胍,搅拌下滴加26.71g40%的2-呋喃甲胺水溶液,后加热至50℃反应,用薄层色谱法(TLC法)跟踪反应进程,待原料硝基胍反应完全后结束反应,约4h。冷却降温,将混合物抽滤、水洗、烘干后得白色粉末16.76g,产率91%。熔点:178~182℃。
1HNMR(500MHz,DMSO),δ/ppm:2.120-2.143(t,J=11.5Hz,1H,NH),2.322(s,2H,NH2),3.767-3.754(d,J=6.5Hz,2H,CH2),6.042-6.061(d,J=9.5Hz,1H,CH),6.233-6.245(t,J=6.0Hz,1H,CH),7.272-7.287(d,J=7.5Hz,1H,CH)。
(2)3-呋喃甲基-4-硝基亚胺四氢-1,3,5-噁二嗪的合成:
合成反应式:
在250mL三口烧瓶中加入1-呋喃甲基-3-硝基胍18.4g(0.10mol),多聚甲醛6.90g(以甲醛的分子量30计,为3-呋喃甲基-4-硝基亚胺四氢-1,3,5-噁二嗪的2.3倍),甲酸60g,,浓磷酸5g,加热至70℃反应,用薄层色谱法(TLC法)跟踪反应进程,待原料反应完全后结束反应,约13h,冷却至常温,用30%氢氧化钠水溶液调PH至6.5左右,抽滤、冰水洗涤、烘干得白色固体19.72g,产率87.2%。熔点:161~164℃。
1HNMR(500MHz,DMSO),δ/ppm:2.304(s,2H,NH2),3.683(s,2H,CH2),4.627-4.630(d,J=1.5Hz,2H,CH2),4.716-4.737(d,J=10.5Hz,2H,CH2),6.047-6.069(d,J=11Hz,1H,CH),6.226-6.240(t,J=7Hz,1H,CH),7.265-7.279(d,J=7Hz,1H,CH)。
(3)3-(2-氯-1,3-噻唑-5-基甲基)-5-呋喃甲基-1,3,5-噁二嗪-4-基叉(硝基)胺的合成:
合成反应式:
在装有搅拌器、温度计和冷凝管的250mL三口烧瓶中,加入3-呋喃甲基-4-硝基亚胺四氢-1,3,5-噁二嗪11.31g(0.05mol)、8.0g无水碳酸钾、1.2g四丁基溴化铵、50ml乙腈,常温搅拌约5min,在室温下滴加含10.3g2-氯-5氯甲基噻唑的乙腈溶液,约2h滴加完毕,加热反应液至65℃恒温反应,用薄层色谱法(TLC法)跟踪反应进程,约11h反应结束,冷却反应液,用二氯甲烷洗涤固体几次,合并洗涤液,旋蒸除去溶剂,加入少量乙酸乙酯和乙醇的混合液,摇晃析出黄色固体,抽滤、烘干得目标产物15.14g,产率84.65%。熔点:166~168℃。
1HNMR(500MHz,DMSO),δ/ppm:3.677(s,2H,CH2),3.802(s,2H,CH2),4.622-4.626(d,J=2Hz,2H,CH2),4.631-4.636(d,J=2.5Hz,2H,CH2),6.050-6.073(d,J=11.5Hz,1H,CH),6.218-6.235(t,J=8.5Hz,1H,CH),7.281-7.294(d,J=6.5Hz,1H,CH),7.416(s,1H,CH)。
制剂实施例
实例2、25%式I化合物悬浮剂的制备:
称取式I化合物25g,硅酸镁铝2g,消泡剂1g,乙二醇4g,SC-6助剂10g,水58g,搅拌均匀。
生物活性测定实施例
实例3、杀虫活性测定
1.对桃蚜活性测定:
取直径6厘米培养皿,皿底覆盖一层滤纸,并滴加适量自来水保湿,从培养桃蚜的甘蓝植株上剪取大小适宜(直径约3厘米)且长有15-30头蚜虫的甘蓝片,去除有蚜翅及叶片正面的蚜虫,调查基数后,叶背向上置于培养皿内,用手持式airbrush喷雾器进行喷雾处理,每处理3次重复,处理后置于标准观察室内,48小时后调查存活虫数,计算死亡率。化合物I在浓度100ppm时对桃蚜的防效较好,死亡率在100%。按照以上方法,已知化合物KC进行杀桃蚜活性平行测定。试验结果见表1。
表1杀桃蚜活性测定结果
由表1结果说明,本发明化合物杀桃蚜活性极显著优于对比已知化合物(KC)。
2.防治稻飞虱田间试验:
选择水稻生长、土壤墒情、水肥条件一致的田块,划分成试验区及空白对照区,各小区面积30m2,设3次重复。试验时水稻长势嫩绿,正值灌浆乳熟期,田间百蔸虫量3万头左右。防治对象为水稻五代褐飞虱。将待试验样品用砂磨机研磨配制成25%悬浮剂,稀释3000倍液,用工农-16型背负式手动喷雾器于稻飞虱卵孵盛期至低龄若虫高发期施药,每亩用量有效成份量为1g,分别于药后1天、3天、7天调查若虫数量。方法是:采用每小区5点取样,每点调查2丛水稻,平行跳跃法调查5点,共计10丛,用盆拍法调查若虫数量。施药前进行基数调查,药后1、3、7天调查残虫量,计算校正防效。
虫口减退率=(处理区药前虫数-处理区药后虫数)/处理区药前虫数×100%
ck0对照区药前;ck1对照区药后;pt0处理区药前;pt1处理区药后。
试验结果见表2。
表2防治稻飞虱试验结果
从表2结果可知,本发明化合物对稻飞虱速效性好,无论是杀虫效果还是持效期均显著优于对比药剂KC。
Claims (3)
1.一种N-芳甲基取代的噁二嗪硝基亚胺衍生物,结构如式I所示:
2.根据权利要求1所述的一种N-芳甲基取代的噁二嗪硝基亚胺衍生物的用途,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组合使用,对农业或林业害虫有防治效果。
3.一种杀虫组合物,含有权利要求1所述的通式I化合物为活性组分和农业、林业上可接受的载体。
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CN1084171A (zh) * | 1992-07-22 | 1994-03-23 | 希巴-盖吉股份公司 | 噁二嗪衍生物 |
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