Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita

Synthesis and nematicidal activities of 1,2,3-benzotriazin-4-one containing 4,5-dihydrothiazole-2-thiol derivatives against Meloidogyne incognita
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含4,5-二氢噻唑-2-硫醇衍生物的1,2,3-苯并三嗪-4-酮的合成及其对南方根结线虫的杀线虫活性

DOI:
10.1080/10426507.2019.1661413
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发表时间:
2020-03
期刊:
Phosphorus, Sulfur, and Silicon and the Related Elements
影响因子:
--
通讯作者:
Xu Xiaoyong
Xu Xiaoyong
中科院分区:
其他
文献类型:
--
作者:
Chen Xiulei;Zhou Zhen;Li Zhong;Xu Xiaoyong

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摘要合成了一系列含4,5-二氢噻唑-2-硫醇的1,2,3-苯并三嗪-4-酮衍生物,并用1H NMR,13 C NMR,19 F NMR和HRMS进行了表征。生物活性测定结果表明,化合物3-(3-((4,5-二氢噻唑-2-基)硫基)丙基)-7-甲氧基苯并[d][1-3]三嗪-4(3 H)-酮,3-(3-((4,5-二氢噻唑-2-基)硫基)丙基)-6-硝基苯并[d][1-3]三嗪-4(3 H)-酮,7-氯-3-甲基-IH-吡唑(3-((4,5-二氢噻唑-2-基)硫基)丙基)苯并[d][1-3]三嗪-4(3 H)-酮在10.0 mg L-1的浓度下对由南方根结线虫引起的黄瓜根结线虫病表现出良好的体内防治效果。化合物7-氯-3-(3-((4,5-二氢噻唑-2-基)硫基)丙基)苯并[d][1-3]三嗪-4(3 H)-酮显示出优异的杀线虫活性,在1.0 mg L-1的浓度下抑制率为68.3%。结果表明,含4,5-二氢噻唑-2-硫醇的1,2,3-苯并三嗪-4-酮的结构可以进一步优化。图形摘要
Abstract A series of novel 1,2,3-benzotriazin-4-one derivatives containing 4,5-dihydrothiazole-2-thiol were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. The bioassay results showed that compounds 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-7-methoxybenzo[d][1–3]triazin-4(3H)-one, 3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)-6-nitrobenzo[d][1–3]triazin-4(3H)-one, 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one exhibited good control efficacy against the cucumber root-knot nematode disease caused by Meloidogyne incognita at the concentration of 10.0 mg L−1 in vivo. Compound 7-chloro-3-(3-((4,5-dihydrothiazol-2-yl)thio)propyl)benzo[d][1–3]triazin-4(3H)-one showed excellent nematicidal activity with inhibition 68.3% at a concentration of 1.0 mg L−1. It suggested that the structure of 1,2,3-benzotriazin-4-one containing 4,5-dihydro-thiazole-2-thiol could be optimized further. Graphical Abstract
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