Synthesis, Herbicidal Activity, and Molecular Mode of Action Evaluation of Novel Quinazolinone—Phenoxypropionate Hybrids Containing a Diester Moiety

Agronomy Pub Date : 2024-09-18 DOI:10.3390/agronomy14092124

Shumin Wang, Na Li, Shibo Han, Shuyue Fu, Ke Chen, Wenjing Cheng, Kang Lei

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Abstract

To develop aryloxyphenoxypropionate herbicides with novel structure and improved activity, a total of twenty-eight novel quinazolinone–phenoxypropionate derivatives containing a diester moiety were designed and synthesized. The herbicidal bioassay results in the greenhouse showed that QPEP-I-4 exhibited excellent herbicidal activity against E. crusgalli, D. sanguinalis, S. alterniflora, E. indica, and P. alopecuroides with inhibition rates >80% at a dosage of 150 g ha−1 and displayed higher crop safety to G. hirsutum, G. max, and A. hypogaea than the commercial herbicide quizalofop-p-ethyl. Studying the herbicidal mechanism by phenotypic observation, membrane permeability evaluation, and transcriptomic analysis revealed that a growth inhibition of plants by QPPE-I-4 was the result from damage of the plants’ biomembrane. The evaluation of ACCase activity in vivo indicated that QPPE-I-4 could inhibit ACCase and may be a new type of ACCase inhibitor. The present work indicated that QPPE-I-4 could represent a lead compound for further developing novel AOPP herbicides.

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含有二酯分子的新型喹唑啉酮-苯氧基丙酸酯杂交化合物的合成、除草活性和分子作用模式评估

为了开发结构新颖、活性更强的芳氧基苯氧基丙酸酯类除草剂，我们设计并合成了 28 种含有二酯分子的新型喹唑啉酮苯氧基丙酸酯类衍生物。在温室中进行的除草生物测定结果表明，QPEP-I-4 对 E. crusgalli、D. sanguinalis、S. alterniflora、E. indica 和 P. alopecuroides 具有优异的除草活性，在 150 g ha-1 的用量下抑制率大于 80%；与商品除草剂 quizalofop-p-ethyl 相比，QPEP-I-4 对 G. hirsutum、G. max 和 A. hypogaea 具有更高的作物安全性。通过表型观察、膜渗透性评估和转录组分析研究其除草机制，发现 QPPE-I-4 对植物生长的抑制是由植物生物膜的破坏造成的。体内 ACC 酶活性评价表明，QPPE-I-4 可抑制 ACC 酶，可能是一种新型的 ACC 酶抑制剂。本研究结果表明，QPPE-I-4 可能是进一步开发新型 AOPP 除草剂的先导化合物。

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Agronomy

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