Design, synthesis and insecticidal activities of novel anthranilic diamides containing polyfluoroalkyl pyrazole moiety

Shi, Jianjun; Ren, Guihua; Wu, Ningjie; Weng, Jian‐Quan; Xu, Ting; Liu, Xinghai; Tan, Cheng‐Xia

doi:10.1016/j.cclet.2017.05.015

Cited by 35 publications

(17 citation statements)

References 27 publications

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“…A series of new dipeptide-chlorantraniliprole conjugates were synthesized by coupling chlorantraniliprole with different dipeptides as shown in Scheme 1. Reacting intermediate 1 with corresponding amino acid methyl ester hydrochlorides led to 2a-b [24,25]. Then, to a solution of compound 2a or 2b in tetrahydrofuran (THF), lithium hydroxide was slowly added.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

Zheng

Lin

et al. 2020

BMC Chemistry

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Phloem systemicity is a desirable property for insecticides to control sucking insects. However, the development of phloem systemic insecticides is challenging. One possible strategy is to link existed insecticides with endogenous substances so that the resulting conjugates can be transported by specific transporters into the phloem. In this study, novel dipeptide promoieties were introduced into chlorantraniliprole, which is an efficient and broad-spectrum anthranilic diamide insecticide without phloem mobility. Twenty-two new dipeptide-chlorantraniliprole conjugates have been synthesized. Systemic tests showed that all conjugates exhibited phloem mobility in Ricinus communis. In particular, compound 4g with alanyl-alanine dipeptide fragment was able to accumulate in phloem sap (114.49 ± 11.10 μM) in the form of its hydrolysis product 5g. Results of bioassay showed that conjugates 4g and 5g were able to exhibit comparable insecticidal activity against Plutella xylostella L. and Spodoptera exigua compared to its parent compound chlorantraniliprole. This work demonstrated that the dipeptide structures were able to contribute to the improvement of the uptake and phloem mobility of chlorantraniliprole, and two phloem mobile conjugates with satisfactory in vivo insecticidal effect was obtained as new candidates for high-efficient insecticides.

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Section: Chemistrymentioning

confidence: 99%

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

Zheng

Lin

et al. 2020

BMC Chemistry

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“…However, as people’s environmental awareness gradually deepens, high-efficiency, low-toxicity, and environmentally friendly pesticides have become an inevitable trend in the creation of new pesticides [ 1 , 2 , 3 ]. There is no doubt that heterocyclic structures are important feature in synthetic pesticides for their high-efficiency, various biological activities, and diversity of possible substituents [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 ]. 1,2,4-Oxadiazole heterocycle, as an important kind of the five-membered oxygen-nitrogen heterocycle, has exhibited a wide range of biological activities in the field of pesticides, such as insecticidal [ 26 , 27 , 28 ], antifungal [ 29 , 30 ], and herbicidal activities [ 31 ].…”

Section: Introductionmentioning

confidence: 99%

1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo

Yang

Ren

et al. 2021

IJMS

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To discover new compounds with broad spectrum and high activity, we designed a series of novel benzamides containing 1,2,4-oxadiazole moiety by bioisosterism, and 28 benzamides derivatives with antifungal activity were synthesized. These compounds were evaluated against four fungi: Botrytis cinereal, FusaHum graminearum, Marssonina mali, and Thanatephorus cucumeris. The results indicated that most of the compounds displayed good fungicidal activities, especially against Botrytis cinereal. For example, 10a (84.4%), 10d (83.6%), 10e (83.3%), 10f (83.1%), 10i (83.3%), and 10l (83.6%) were better than pyraclostrobin (81.4%) at 100 mg/L. In addition, the acute toxicity of 10f to zebrafish embryo was 20.58 mg/L, which was classified as a low-toxicity compound.

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“…This novel scaffold of anthranilic diamides attracts great attention and many efforts have been devoted by researchers for the structural modification of chlorantraniliprole. Most reports were mainly focused on three parts: the aliphatic amide 1 [15][16][17][18][19], the amide bridge 2 [19][20][21][22][23], and the Npyridylpyrazole 3 [24][25][26][27][28][29][30][31][32][33][34][35]. Based on these modifications, structures such as cyantraniliprole, tetrachlorantraniliprole, cyclaniliprole, and tetraniliprole were developed thereafter (Figure 1) [36][37][38].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of N‐pyridylpyrazole derivatives containing 3‐thioethers

Sun

Zhang

et al. 2021

Journal of Heterocyclic Chem

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Thioether and its derivatives are important active pharmacophores, widely adopted in the molecular design of agrochemicals. The introduction of thioether into drug intermediate is important to improve the liposolubility, hydrophobicity, and bioactivity of molecules. For development of novel insecticides targeting at ryanodine receptor (RyR), a series of anthranilic diamides of N‐pyridylpyrazole derivatives containing 3‐thioether were designed and synthesized. The structures of these compounds were verified using 1H NMR, 13C NMR, and HRMS. Their insecticidal activities against Mythimna separata (M. separata, oriental armyworms) and Plutella xylostella (P. xylostella, diamondback moths) were evaluated and the preliminary structure–activity relationship (SAR) was discussed, among which 9f, 9g exhibited favorable insecticidal activities against M. separata at 5 mg/L (9f, 50%; 9g, 40%). In addition, insecticidal activity of the intermediate 8 indicated that bromomethyl group at 3‐position of pyrazole moiety has an important impact for retaining insecticidal activity. Calcium imaging experiment and molecular docking were carried out to elaborate insecticidal mechanism from the perspective of experiment and molecular simulation, respectively.

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Design, synthesis and insecticidal activities of novel anthranilic diamides containing polyfluoroalkyl pyrazole moiety

Cited by 35 publications

References 27 publications

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

Synthesis, bioactivities and phloem uptake of dipeptide-chlorantraniliprole derivatives

1,2,4-Oxadiazole-Based Bio-Isosteres of Benzamides: Synthesis, Biological Activity and Toxicity to Zebrafish Embryo

Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of N‐pyridylpyrazole derivatives containing 3‐thioethers

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