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Design, Synthesis, and Herbicidal Activity of Novel Tetrahydrophthalimide Derivatives Containing Oxadiazole/Thiadiazole Moieties.
Geng, Wang; Zhang, Qi; Liu, Li; Tai, Gangyin; Gan, Xiuhai.
Afiliación
  • Geng W; State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
  • Zhang Q; State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
  • Liu L; State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
  • Tai G; State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
  • Gan X; State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
J Agric Food Chem ; 72(31): 17191-17199, 2024 Aug 07.
Article en En | MEDLINE | ID: mdl-39054861
ABSTRACT
Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) has a high status in the development of new inhibitors. To develop novel and highly effective PPO inhibitors, active substructure linking and bioisosterism replacement strategies were used to design and synthesize novel tetrahydrophthalimide derivatives containing oxadiazole/thiadiazole moieties, and their inhibitory effects on Nicotiana tobacco PPO (NtPPO) and herbicidal activity were evaluated. Among them, compounds B11 (Ki = 9.05 nM) and B20 (Ki = 10.23 nM) showed significantly better inhibitory activity against NtPPO than that against flumiclorac-pentyl (Ki = 46.02 nM). Meanwhile, compounds A20 and B20 were 100% effective against three weeds (Abutilon theophrasti, Amaranthus retroflexus, and Portulaca oleracea) at 37.5 g a.i./ha. It was worth observing that compound B11 was more than 90% effective against three weeds (Abutilon theophrasti, Amaranthus retroflexus, and Portulaca oleracea) at 18.75 and 9.375 g a.i./ha. It was also safer to rice, maize, and wheat than flumiclorac-pentyl at 150 g a.i./ha. In addition, the molecular docking results showed that compound B11 could stably bind to NtPPO and it had a stronger hydrogen bond with Arg98 (2.9 Å) than that of flumiclorac-pentyl (3.2 Å). This research suggests that compound B11 could be used as a new PPO inhibitor, and it could help control weeds in agricultural production.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Oxadiazoles / Ftalimidas / Tiadiazoles / Diseño de Fármacos / Amaranthus / Inhibidores Enzimáticos / Protoporfirinógeno-Oxidasa / Malezas / Simulación del Acoplamiento Molecular / Herbicidas Idioma: En Revista: J Agric Food Chem Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Oxadiazoles / Ftalimidas / Tiadiazoles / Diseño de Fármacos / Amaranthus / Inhibidores Enzimáticos / Protoporfirinógeno-Oxidasa / Malezas / Simulación del Acoplamiento Molecular / Herbicidas Idioma: En Revista: J Agric Food Chem Año: 2024 Tipo del documento: Article País de afiliación: China Pais de publicación: Estados Unidos