Synthesis, Larvicidal Activities and Antifungal Activities of Novel Chlorantraniliprole Derivatives and Their Target in the Ryanodine Receptor

Chen, Qichao; Xiong, Lixia; Luo, Min; Wang, Jin; Hu, Changyan; Zhang, Xiao; Shibata, Yu; Li, Yonghong; Sun, Dequn

doi:10.3390/molecules20033854

Cited by 10 publications

(6 citation statements)

References 19 publications

(27 reference statements)

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“…Due to the discovery of the excellent performance of flubendiamide A (Figure 1), chlorantraniliprole B (Figure 1), and pyflubumide (Figure 2) against pest insects and phytophagous mites in crop protection and their subsequent commercialization, the design and synthesis of new compounds containing diamide groups has become a major trend in the search for potential compounds with insecticidal and acaricidal activities [14,15].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Novel 1,3,5-Trimethylpyrazole-Containing Malonamide Derivatives

Liao

Liu

et al. 2019

Molecules

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New 1,3,5-trimethylpyrazole-containing malonamide derivatives based on pyflubumide were designed, synthesized, and characterized using 1H-NMR, 13C-NMR, and high-resolution mass spectra (HRMS). The results of preliminary bioassays showed that the target compounds possessed good activities against Tetranychus cinnabarinus, Plutella xylostella, and Aphis craccivora. Most of the target compounds exhibited moderate to good acaricidal activity against Tetranychus cinnabarinus at a concentration of 400 µg/mL, and some showed moderate activity at a concentration of 200 µg/mL; in particular, compounds 8m and 8p exhibited 70.0% mortality. In addition, some of the target compounds exhibited good insecticidal activities against Plutella xylostella at a concentration of 200 µg/mL, especially compounds 8i and 8o, which achieved 100.0% mortality at a concentration of 100 µg/mL. Interestingly, some of the target compounds exhibited potent anti-aphid activity against Aphis craccivora at a concentration of 200 µg/mL; furthermore, compounds 8p and 8q demonstrated 100.0% anti-aphid activity at a concentration of 50 µg/mL. The preliminary analyses of the structure–activity relationships (SAR) indicated that the acaricidal and insecticidal activities varied significantly depending on the type of substituent and substitution pattern, which provides guidance for the further investigation of such structural modifications.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Activities of Novel 1,3,5-Trimethylpyrazole-Containing Malonamide Derivatives

Liao

Liu

et al. 2019

Molecules

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“…(Scheme 2) 21,22 To a dry round-bottomed flask containing a solution of dry triethylamine (TEA) (12 mmol) in anhydrous CH 3 CN (30 mL), methyl glycinate (or ethyl glycinate) (12 mmol) was added under nitrogen. The reaction mixture was stirred for 30 min at room temperature.…”

Section: Synthesis Of Compounds 7b 7c 8b 8c 9b and 9cmentioning

confidence: 99%

Novel amino acid ester–chlorantraniliprole conjugates: design, synthesis, phloem accumulation and bioactivity

Yao

Wen

Zhao

et al. 2017

Pest Management Science

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“…This insecticide affects the ryanodine receptors that regulate the release of intracellular calcium stores critical for muscle contraction (Lahm et al, 2007). Chlorantraniliprole is already registered for application in potato crops in several potato‐producing countries (EPA, 2008; PPDB Management Team, 2019) and previous studies have shown its promising ovicidal and larvicidal effects against lepidopteran pest species (Bassi, Rison, & Wiles, 2009; Chen et al, 2015; Ioriatti, Anfora, Angeli, Mazzoni, & Trona, 2009). Although it has been demonstrated that chlorantraniliprole affects a broad range of lepidopteran species (Hannig, Ziegler, & Marçon, 2009; Lahm et al, 2007), no study to date has explored the toxic effects of chlorantraniliprole on the potato tuber moth T. solanivora in a comprehensive way.…”

Section: Introductionmentioning

confidence: 99%

Toxic effect of chlorantraniliprole on new‐born larvae of the potato tuber moth Tecia solanivora (Lepidoptera: Gelechiidae)

Bacca

Cabrera

Gutiérrez³

2021

Annals of Applied Biology

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The potato tuber moth Tecia solanivora is an invasive species threatening potato crops and stored tubers. Previous studies have shown that South American populations of this species have evolved insecticide resistance to major classes of insecticides (i.e., pyrethroids, carbamates and organophosphates). Therefore, testing for other methods of pest control is of increasing importance. In this study, we evaluated the toxic effect of chlorantraniliprole against early immature stages of T. solanivora. We carried out a concentration–mortality bioassay using eggs. Subsequently, we subjected eggs to several insecticide application scenarios and evaluated hatching success, larvae activity and overall mortality of immature stages. Additionally, we analysed the hatching behaviour of larvae when the eggs were treated with chlorantraniliprole. After the concentration–mortality bioassay, we calculated an LC50 of 298.6 ppm, yet the mortality did not occur during the egg‐phase, but rather the neonate larvae experienced the toxic effects of chlorantraniliprole. In the subsequent exposure‐mode bioassay, the hatching success was overall high in all treatments, and larvae mortality reached 100% regardless of exposure mode. Consequently, larvae activity was severely reduced when in contact with the insecticide. Furthermore, when eggs are subjected to such LC50 dose, larvae manage to break through the chorion, but after releasing the legs, each hatching stages takes longer than the previous. Our results highlight the potential use of chlorantraniliprole for the control of T. solanivora in stored potato tubers. Additionally, chlorantraniliprole appears to be a promising alternative for the control of T. solanivora populations resistant to neurotoxic insecticides.

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Synthesis, Larvicidal Activities and Antifungal Activities of Novel Chlorantraniliprole Derivatives and Their Target in the Ryanodine Receptor

Cited by 10 publications

References 19 publications

Design, Synthesis, and Biological Activities of Novel 1,3,5-Trimethylpyrazole-Containing Malonamide Derivatives

Design, Synthesis, and Biological Activities of Novel 1,3,5-Trimethylpyrazole-Containing Malonamide Derivatives

Novel amino acid ester–chlorantraniliprole conjugates: design, synthesis, phloem accumulation and bioactivity

Toxic effect of chlorantraniliprole on new‐born larvae of the potato tuber moth Tecia solanivora (Lepidoptera: Gelechiidae)

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