Trifluoromethylpyridine: An Important Active Fragment for the Discovery of New Pesticides

Zheng, Zhiguo; Dai, Ali; Jin, Zhichao; Robin, Yonggui; Wu, Jian

doi:10.1021/acs.jafc.1c08383

Cited by 32 publications

(23 citation statements)

References 40 publications

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“…Moreover, the unique electronic effects and fat-soluble penetration effects of trifluoromethyl pyridine could greatly affect the conformation and metabolism of compounds ( Zheng et al., 2022 ). It has become one of the main active structures of many commercial pesticides, such as the herbicide pyroxsulam ( Nugent et al., 2015 ), the insecticide fluazuron ( Cai et al., 2010 ; Chen et al., 2019 ), and the fungicide fluopyram ( Xie et al., 2014 ), etc ( Figure 1C ).…”

Section: Introductionmentioning

confidence: 99%

Novel trifluoromethylpyridine piperazine derivatives as potential plant activators

et al. 2022

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Plant virus diseases seriously affect crop yield, especially tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). The development of plant immune activators has been an important direction in the innovation of new pesticides. Therefore, we designed and synthesized a series of trifluoromethyl pyridine piperazine derivatives (A1-A27), and explored the action mechanism of active compound. The antiviral activity test showed that compounds A1, A2, A3, A9, A10, A16, A17 and A21 possessed higher activities than commercialized ningnanmycin. Particularly, the in vivo antiviral activity indicated that compound A16 showed the most potent protective activity toward TMV (EC50 = 18.4 μg/mL) and CMV (EC50 = 347.8 μg/mL), compared to ningnanmycin (50.2 μg /mL for TMV, 359.6 μg/mL for CMV). The activities of defense enzyme, label -free proteomic and qRT-PCR analysis showed that compound A16 could enhance the defensive enzyme activities of superoxide dismutase (SOD),polyphenol oxidase (PPO) and phenylalanine ammonialyase (PAL), and activate the phenylpropanoid biosynthesis pathway to strenthen the antiviral activities of tobacco. This study provides reliable support for the development of new antiviral pesticides and potential antiviral mechanism.

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Section: Introductionmentioning

confidence: 99%

Novel trifluoromethylpyridine piperazine derivatives as potential plant activators

et al. 2022

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“…We have long been devoted into the search and development of novel small molecular structures for pesticide innovations and applications. [125][126][127][128][129][130][131][132][133] Therefore, we are very interested in their potential applications as leading structures for the development of novel pesticides. Two of the most signi cant plant pathogens of Xanthomonas oryzae pv.…”

Section: Resultsmentioning

confidence: 99%

Facile Access to Benzofuran Derivatives through Radical Reactions with Heteroatom-centered Super-electron-donors

Robin

Jiang

Wang

et al. 2023

Preprint

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Heteroatom anions are applied as super-electron-donors (SEDs) to initiate radical reactions for facile synthesis of 3-substituted benzofurans. Phosphines, thiols and anilines bearing different substitution patterns work well in this inter-molecular radical coupling reaction and the 3-functionalized benzofuran products bearing heteroatomic functionalities are given in moderate to excellent yields. The reaction mechanism is elucidated via control experiments and computational methods. The afforded products showed promising applications in both organic synthesis and pesticide development.

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“…Chemical tools have proven to be effective in plant protection against harmful insects, weeds and various plant pathogens, including bacteria, fungi and viruses. [16][17][18] The development and application of green pesticides have made significant contributions to reducing economic loss in world agricultural production. Encouraged by achievements in the development of small molecular green pesticides, we aimed to explore novel chemical structures for the effective control of significant plant viruses such as PVY to facilitate a highly effective plant protection strategy and a clear antiviral mechanism.…”

Section: Introductionmentioning

confidence: 99%

Development of axially chiral urazole scaffolds for antiplant virus applications againstpotato virus Y

Jin

Mou

Zou

et al. 2023

Pest Management Science

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BACKGROUND Potato virus Y (PVY) was first discovered by Smith in 1931 and is currently ranked as the fifth most significant plant virus. It can cause severe damage to plants from the family Solanaceae, which results in billions of dollars of economic loss worldwide every year. To discover new antiviral drugs, a class of multifunctional urazole derivatives bearing a stereogenic CN axis were synthesized with excellent optical purities for antiviral evaluations against PVY. RESULTS The absolute configurations of the axially chiral compounds exhibited obvious distinctions in antiviral bioactivities, with several of these enantio‐enriched axially chiral molecules showing excellent anti‐PVY activities. In particular, compound (R)‐9f exhibited remarkable curative activities against PVY with a 50% maximal effective concentration (EC50) of 224.9 μg mL−1, which was better than that of ningnanmycin (NNM), which had an EC50 of 234.0 μg mL−1. And the EC50 value of the protective activities of compound (R)‐9f was 462.2 μg mL−1, which was comparable to that of NNM (442.0 μg mL−1). The mechanisms of two enantiomer of the axially chiral compounds 9f were studied by both molecule docking and defensive enzyme activity tests. CONCLUSION Mechanistic studies demonstrated that the axially chiral configurations of the compounds played significant roles in the molecule PVY‐CP (PVY Coat Protein) interactions and could enhance the activities of the defense enzymes. The (S)‐9f showed only one carbon–hydrogen bond and one π–cation interaction between the chiral molecule and the PVY‐CP amino acid sites. In contrast, the (R)‐enantiomer of 9f exhibited three hydrogen bonding interactions between the carbonyl groups and the PVY‐CP active sites of ARG157 and GLN158. The current study provides significant information on the roles that axial chiralities play in plant protection against viruses, which will facilitate the development of novel green pesticides bearing axial chiralities with excellent optical purities. © 2023 Society of Chemical Industry.

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Trifluoromethylpyridine: An Important Active Fragment for the Discovery of New Pesticides

Cited by 32 publications

References 40 publications

Novel trifluoromethylpyridine piperazine derivatives as potential plant activators

Novel trifluoromethylpyridine piperazine derivatives as potential plant activators

Facile Access to Benzofuran Derivatives through Radical Reactions with Heteroatom-centered Super-electron-donors

Development of axially chiral urazole scaffolds for antiplant virus applications againstpotato virus Y

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