CN108329263A - 一种1,8-萘二甲酰亚胺酰胺类化合物及其用途 - Google Patents
一种1,8-萘二甲酰亚胺酰胺类化合物及其用途 Download PDFInfo
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
本发明公开了一种1,8‑萘二甲酰亚胺酰胺类化合物及其合成方法和用途，其结构如通式I所示：式中：R选自：
Description
技术领域 本发明属于农用杀螨剂领域，具体涉及一种1,8-萘二甲酰亚胺酰胺类化合物及其用途。
背景技术 目前常用的杀螨剂主要有季酮酸类、丙烯腈类、肼基甲酸酯类、吡唑类等，但由于螨类在形态、习性及栖息场所等方面具有多样性，分布广，适应性强，种类繁多，繁殖能力极强，所以经过多代迭代后容易产生抗性，短时间内能给农林业造成巨大损失。又由于大面积长时间单一使用，加快了抗性的进程。为了应对出现的抗性问题，在保证绿色环保的前提下，开发低毒高效具有新结构、新作用机制的农药是目前的发展趋势。专利CN103641781 B公布了一种萘二酰亚胺类化合物及其盐作为植物生长调节剂的应用。萘二甲酰亚胺作为一种活性结构，已引起科研工作者的广泛注意。在现有技术中，如本发明所述的一种萘二酰亚胺类化合物作为杀螨剂还未见报道。
发明内容 本发明的目的是提供一种结构新颖、生产及使用安全、杀螨效果好、防治成本低的1,8-萘二甲酰亚胺酰胺杀螨剂，可用于农业或林业害螨的防治。
本发明的技术方案如下：
一种1,8-萘二甲酰亚胺酰胺类化合物，如通式I所示：
式中：R选自
本发明通式I化合物可由如下方法制备；
式III化合物(1,8-萘二甲酸酐)与1,2-乙二胺化合物以水或者乙醇做溶剂，在60-100℃反应2h，可制得式Ⅱ化合物。由式Ⅱ化合物制备通式Ⅰ化合物时，溶剂可以用二氯甲烷、三氯甲烷、乙酸乙酯、乙腈、甲苯等有机溶剂；缚酸剂可用无机碱碳酸钠、碳酸钾，有机碱三乙胺。通式Ⅰ与通式II化合物的制备见本发明实施例合成实例。通式Ⅰ化合物的结构与物理性质列于表1。制得的通式Ⅰ化合物的生物活性测试与常用杀螨剂螺螨酯进行对比实验。
表1通式Ⅰ化合物的结构与物理性质
本发明的优点和积极效果：
本发明化合物(式I)将萘二酰亚胺结构和酰胺或氨基甲酸酯引入杀螨剂结构中，具有显著的结构新颖性。此类一种1,8-萘二甲酰亚胺酰胺化合物对螨卵有显著的抑杀效果，表现出超高效性的显著优点。在1ppm对朱砂叶螨螨卵的杀灭率在80％以上，特别是化合物1和化合物3分别达92％和95％，显著高于同浓度下商品螺螨酯(86％)；化合物2和化合物4基本与螺螨酯相当。此外，本发明合成的通式I类化合物具有合成步骤简单、生产成本低、三废低的优点。而且本发明化合物为氮环类、酰胺或酯类化合物，具有对有益生物低毒性、易降解、环境相容性好的特点，具有作为创制性杀螨剂新品种产业化的前景。
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组合使用以提高产品的综合性能。
本发明还包括以通式I化合物为活性组分的杀虫组合物，其中活性组分在组合物的重量百分含量为1-99％，该杀虫组合物还包括农业或林业上可接受的载体。
本发明的组合物可以以制剂的形式施用。通式I化合物作为活性组分溶解或分散于载体或溶剂中，添加适当的表面活性剂配置乳油、悬浮剂、微乳剂和可湿性粉剂等。
应该明确的是，在本发明的权利要求所限定的范围内，可进行各种变换或改动。
具体实施方式
下列合成实施例或生测实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3的制备
(1)N-(2-氨乙基)-1,8-萘酰亚胺的合成
向250mL反应瓶中分别加入39.6g(0.2mol)1,8-萘二甲酸酐、100mL水和30mL乙酸、30g(0.5mol)1,2-乙二胺，回流4h，反应液中的固体由淡黄色针状晶体逐渐变成白色固体，薄层色谱(TLC)检测原料消失，降至室温，抽滤，滤液收集回收套用，将滤饼烘干，得白色固体39.4g，收率82％。
(2)对叔丁基苯甲酰氯的合成
向250mL三口反应瓶中加入17.8g(0.1mol)对叔丁基苯甲酸、80g甲苯、14.3g(0.12mol)SOCl2，缓慢升温至80℃，保温反应2h，减压蒸馏除去过量的氯化亚砜和甲苯，馏分收集回收套用，得黄色油状液体19.5g，收率99％。
(3)4-叔丁基-N-(2-(1,8-萘酰亚胺)乙基)苯甲酰胺的合成
向250mL反应瓶中分别加入24g(0.1mol)N-(2-氨乙基)-1,8-萘酰亚胺、100mL二氯甲烷和12.1g(0.12mol)三乙胺，室温下滴加对叔丁基苯甲酰氯23.6g(0.12mol)，薄层色谱(TLC)检测原料Ⅱ消失，抽滤，水洗，烘干得白色固体36g，收率90％。熔点：206.5～209.1℃1H NMR(500MHz，DMSO-d6)δ(ppm)：8.47(t,1H),8.42(d,2H),8.38(d,2H),7.79(d,2H),7.60(d,2H),7.38(d,2H),4.24(t,2H),3.60(q,2H),1.24(s,9H).
实例2、化合物4的制备
(1)N-(2-氨乙基)-1,8-萘酰亚胺的合成，方法同实例1
(2)4-氯-3-甲基-1-乙基吡唑-5-甲酰氯的合成
向250mL三口反应瓶中加入18.9g(0.1mol)4-氯-3-甲基-1-乙基吡唑-5-甲酸、80mL甲苯、17.9g(0.15mol)SOCl2，缓慢升温至80℃，保温反应4h，减压蒸馏除去过量的氯化亚砜和甲苯，馏分收集回收套用，得棕色油状液体20.1g，收率98％。
(3)4-氯-3-甲基-1-乙基-5-[N-(2-(1,8-萘酰亚胺)乙基)]吡唑甲酰胺的合成
向250mL反应瓶中分别加入24g(0.1mol)N-(2-氨乙基)-1,8-萘酰亚胺、100mL乙腈和12.1g(0.12mol)三乙胺，室温下滴加4-氯-3-甲基-1-乙基吡唑-5-甲酰氯24.8g(0.12mol)，薄层色谱(TLC)检测原料Ⅱ消失，加50mL水并搅拌10min，抽滤，水洗，烘干得白色固体37.8g，收率92％。熔点：185.5～188.3℃，1H NMR(500MHz，DMSO-d6)δ(ppm)：8.51(t,1H),8.40(d,2H),8.36(d,2H),7.66(dd,2H),4.29(q,2H),3.77(s,3H),3.59(q,2H),2.43(t,2H),1.08(t,3H).
按照以上方法，以氯甲酸正丁酯、氯甲酸异丁酯与化合物Ⅱ反应可分别得到化合物1和2，1H NMR(500MHz，DMSO-d6),δ(ppm)数据如下：
化合物1:8.53(d,2H),8.49(d,2H),7.91(dd,2H),7.25(t,1H),4.23(t,2H),3.91(t,2H),3.40(q,2H),1.51–1.41(m,2H),1.34–1.26(m,2H),0.91(t,3H).
化合物2:8.60(d,2H),8.56(d,2H),8.01(dd,2H),7.25(t,1H),4.59–4.55(m,1H),4.30(t,2H),3.58–3.52(m,2H),1.54–1.48(m,2H),1.15(d,3H),0.89(t,3H).
生物活性测定
实例3、杀螨活性测定
对朱砂叶螨螨卵活性具体测定方法：
根据《农药室内生物测定试验准则》标准，采用浸渍法。将供试药剂按有效成分分别稀释至所需浓度，将载有朱砂叶螨螨卵(螨卵按室内标准化方法正常饲养的群体)的叶片浸入药液中，轻轻振荡5s后取出。吸去叶片上多余的药液，置于铺有润湿滤纸的培养皿内，用透光性好的保鲜膜覆盖，以不含药剂的处理做空白对照，将培养皿放在(25±1)℃恒温培养箱内饲养和观察，待对照卵孵化并发育至弱螨阶段时调查孵化数，统计校正害虫死亡率。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化合物Ⅰ与已知化合物螺螨酯杀朱砂叶螨螨卵活性数据
从表2生测结果看出，本发明部分化合物1、3较已知化合物螺螨酯对朱砂叶螨有更高的活性。
Claims (3)
1.一种1,8-萘二甲酰亚胺酰胺类化合物，结构如通式I所示：
式中：R选自：
2.根据权利要求1所述的一种1,8-萘二甲酰亚胺酰胺类化合物的用途，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，用于防治农业害螨。
3.一种杀螨组合物，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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