Synthesis of Hinokitiol Sulfonate Derivatives and Their Anti‐Oomycete and Nematicidal Activities

Che, Zhiping; Liu, Yibo; Chen, Luyao; Xing, Puhou; Li, Xiangdong; Huang, Xiaobo; Liu, Shengming; Chen, Genqiang; X, Lin; Tian, Yuee

doi:10.1002/cbdv.202200580

Cited by 7 publications

(1 citation statement)

References 32 publications

(111 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although they have alleviated the threat of agricultural pests and diseases to some extent, they also caused serious problems, such as pesticide residues, environmental pollution, and threats to non-target creatures . Therefore, people have been exploring alternatives to traditional chemical pesticides, and natural-product-based pesticides have received much attention recently on account of their characteristics, such as relative safety, easy degradation, and environmental compatibility. − …”

Section: Introductionmentioning

confidence: 99%

Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates

Yang

Liu

Han

et al. 2022

J. Agric. Food Chem.

View full text Add to dashboard Cite

To discover novel natural-product-based insecticide candidates, herein, a variety of osthole-derived Nbenzoylthioureas were synthesized and assessed for their insecticidal activities against three insect pests. An insecticidal assay showed that most of the target osthole-derived N-benzoylthioureas displayed a more potent and broad-spectrum insecticidal effect than the parent osthole after the introduction of N-benzoylthioureas on the C-3′ position of osthole. Compound B24 displayed the most potent growth inhibitory (GI) effect on Mythimna separata Walker, with a final corrected mortality rate of 82.1% when treated with a concentration of 1 mg/mL, which was 1.64-and 1.53-fold higher in comparison to osthole and the botanical insecticide toosendanin, respectively. Compounds B22, B23, and B25 displayed a more promising aphicidal effect on Myzus persicae Sulzer, and their LD 50 values were 0.015, 0.017, and 0.019 μg/larvae, respectively, superior to the commercially available insecticide rotenone (0.024 μg/larvae). Derivatives B19, B20, B23, and B25 displayed more potent larvicidal activity against Plutella xylostella Linnaeus, with LC 50 values of 0.22, 0.26, 0.15, and 0.30 mg/mL, respectively, exceeding that of rotenone (0.37 mg/mL). Furthermore, both compounds B19 and B23 against P. xylostella were found to be more effective than rotenone in a control efficacy assay under greenhouse conditions. The structure−activity relationship (SAR) suggested that osthole-derived N-benzoylthioureas are more active in most cases when the R group is an electron-withdrawing group than when it is an electron-donating group, especially for halogenated groups. Additionally, the potent compounds B19 and B23 possessed good selectivity and were less toxic to non-target organisms. This study suggests that these osthole-derived N-benzoylthioureas could be further studied in depth as eco-friendly natural product pesticides in crop protection.

show abstract

Section: Introductionmentioning

confidence: 99%

Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates

Yang

Liu

Han

et al. 2022

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

Che

Chen

Zhang

et al. 2023

Chemistry & Biodiversity

View full text Add to dashboard Cite

Using cinchona alkaloid as the lead compound, twenty-four cinchona alkaloid sulfonate derivatives (1 a-l, 2 a-c, 3 a-c, 4 ac, and 5 a-c) were designed and prepared by modifying their C9 position, and structurally confirmed by 1 H-NMR, 13 C-NMR, HR-MS and melting points. Moreover, the stereochemical configurations of compounds 1 f and 1 l were unambiguously confirmed by single-crystal X-ray diffraction. Furthermore, we determined the anti-oomycete and anti-fungal activities of these target compounds against Phytophthora capsici and Fusarium graminearum in vitro. The results showed that two compounds 4 b and 4 c exhibited prominent anti-oomycete activity, and the median effective concentration (EC 50 ) values of 4 b and 4 c against P. capsici were 22.55 and 16.32 mg/L, respectively. This study suggested that when the C9 position of cinchona alkaloid sulfonate derivatives is in the S configuration and the 6'-position methoxy group is not present, the anti-oomycete activity is superior. In addition, five compounds 1 e, 1 f, 1 k, 3 c and 4 c displayed significant anti-fungal activity, with EC 50 values of 43.64, 45.07, 80.18, 48.58 and 41.88 mg/L against F. graminearum, respectively. This result indicates that only when a specific substituent is introduced into the structural framework of the target compound, the corresponding compound exhibits significant inhibitory activity against fungi.

show abstract

Design, synthesis, and anti-oomycete activity of 3-acyloxymaltol/ethyl maltol derivatives

Guo,

Liu,

et al. 2024

Journal of Asian Natural Products Research

View full text Add to dashboard Cite

Synthesis of Hinokitiol Sulfonate Derivatives and Their Anti‐Oomycete and Nematicidal Activities

Cited by 7 publications

References 32 publications

Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates

Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates

Synthesis, Anti‐Oomycete and Anti‐fungal Activities of Novel Cinchona Alkaloid Derivatives Containing Sulfonate Moiety

Design, synthesis, and anti-oomycete activity of 3-acyloxymaltol/ethyl maltol derivatives

Contact Info

Product

Resources

About