Acaricidal and insecticidal efficacy of new esters derivatives of a natural coumarin osthole

Shan, Xijie; Lv, Min; Wang, Jingru; Qin, Yujia; Xu, Hui

doi:10.1016/j.indcrop.2022.114855

Cited by 14 publications

(24 citation statements)

References 30 publications

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“…separata, which had slow-acting insecticidal effects. , Among these target osthole-derived N -benzoylthioureas, compounds B6 , B7 , B10 , B17 , B19 , B21 , and B24 showed more potent GI activity, with CMRs over 70% at 30 days, which was superior to toosendanin (53.6%). Especially, compound B24 exhibited the most potent GI activity, with a final CMR of 82.1%, exceeding the reported osthole-based esters . The structure–activity relationship (SAR) indicated that the corresponding derivative is more active in most cases when R is an electron-withdrawing group, especially when it is a dihalogenated group than when R is an electron-donating group.…”

Section: Resultsmentioning

confidence: 92%

“…sepatata but also M. persicae, with a broader spectrum of insecticidal activity compared to some previously reported osthole derivatives. , Additionally, as for the aphicidal activity, we found that, similar to the SAR of the derivatives against M. sepatata, the aphicidal activity of osthole-derived N -benzoylthioureas is lower when R is an electron-donating group than when R is an electron-withdrawing group, especially for halogenated groups; e.g., the CMRs of compounds B11 (R = 2-CH 3 ), B12 (R = 3-CH 3 ), and B14 (R = 3-OCH 3 ) against M.…”

Section: Resultsmentioning

confidence: 99%

“…Especially, compound B24 exhibited the most potent GI activity, with a final CMR of 82.1%, exceeding the reported osthole-based esters. 22 The structure−activity relationship (SAR) indicated that the corresponding derivative is more active in most cases when R is an electron-withdrawing group, especially when it is a dihalogenated group than when R is an electron-donating group. For example, the CMRs of compounds B11 (R = 2-CH 3 ), B13 (R = 4-CH 3 ), and B15 (R = 4-OCH 3 ) at 30 days were 42.9, 46.4, and 39.3%, respectively, while the CMRs of compounds B21 (R = 2,4-di-Cl), B24 (R = 3,5-di-Cl), and B27 (R = 3,4-di-F) at 30 days were 75.0, 82.1, and 64.3%, respectively.…”

Section: Data Formentioning

confidence: 99%

“…This result indicated that these osthole-derived N-benzoylthioureas had good insecticidal activity against not only M. sepatata but also M. persicae, with a broader spectrum of insecticidal activity compared to some previously reported osthole derivatives. 21,22 Additionally, as for the aphicidal activity, we found that, similar to the SAR of the derivatives against M. sepatata, the aphicidal activity of osthole-derived N-benzoylthioureas is lower when R is an electron-donating group than when R is an electron-withdrawing group, especially for halogenated groups; e.g., the CMRs of compounds B11 (R = 2-CH 3 ), B12 (R = 3-CH 3 ), and B14 (R = 3-OCH 3 ) against M. persicae were 52.6, 35.1, and 45.6%, whereas the CMRs of compounds B16 (R = 4- Larvicidal Activity of Osthole-Derived N-Benzoylthioureas against P. xylostella. The leaf disk-dipping assay was used to evaluate the larvicidal activity of compounds B1−B29 against P. xylostella in accordance with some previous reports.…”

Section: Data Formentioning

confidence: 99%

“…Currently, the marketed thiourea pesticides include methyl-thiophanate, diafenthiuron, and chloromethiuron (Figure ). Previously, some osthole-based esters and isoxazoline derivatives , have been reported to possess good insecticidal activity against Mythimna separata and Plutella xylostella, but to our knowledge, the introduction of active thiourea moieties of such listed thiourea pesticides (Figure ) into the structure of osthole has not been reported. In light of the above, we envisage that the introduction of the thiourea moiety at the C-3′ position of osthole using an active substructure splicing strategy may yield osthole derivatives with more potent and broad-spectrum insecticidal activities (Figure ).…”

Section: Introductionmentioning

confidence: 99%

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

Yang

Liu

Han

et al. 2022

J. Agric. Food Chem.

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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.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Data Formentioning

confidence: 99%

Section: Data Formentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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

Yang

Liu

Han

et al. 2022

J. Agric. Food Chem.

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Plant natural product‐based pesticides in crop protection: semi‐synthesis, mono‐crystal structures and agrochemical activities of osthole ester derivatives, and study of their toxicology against Tetranychus cinnabarinus (Boisduval)

Hao,

Jiang,

et al. 2024

Pest Management Science

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BACKGROUNDOwing to large amounts of synthetic pesticides being extensively and unreasonably used for crop protection, currently, resistance and negative impacts on human health and environment safety have appeared. Therefore, development of potential pesticide candidates is highly urgent. Herein, a series of ester derivatives of osthole were designed and synthesized as pesticidal agents.RESULTSSix spatial configurations of 4′‐(p‐toluenoyloxy)osthole (4b), 4′‐(m‐fluorobenzoyloxy)osthole (4f), 4′‐(p‐fluorophenylacetyloxy)osthole (4m), 4′‐(3′′,4′′‐methylenedioxybenzoyloxy)osthole (4q), 4′‐formyloxyosthole (4u) and 4′‐acetyloxyosthole (4v) were determined by X‐ray mono‐crystal diffraction. Compounds 4b, 4′‐(p‐chlorobenzoyloxy)osthole (4g), 4′‐(m‐chlorobenzoyloxy)osthole (4h), 4′‐(p‐bromobenzoyloxy)osthole (4i) and 4′‐(2′′‐chloropyridin‐3′′‐ylcarbonyloxy)osthole (4p) showed higher insecticidal activity than toosendanin against Mythimna separata Walker; notably, compound 4b displayed 1.8 times insecticidal activity of the precursor osthole. Against Tetranychus cinnabarinus Boisduval, compounds 4g and 4h showed 3.3 and 2.6 times acaricidal activity of osthole, and good control effects in the glasshouse. Scanning electron microscopy assay demonstrated that compound 4g can damage the cuticle layer of T. cinnabarinus resulting in death.CONCLUSIONCompounds 4g and 4h can be further studied as lead pesticidal agents for the management of M. separata and T. cinnabarinus. These results will pave the way for application of osthole derivatives as agrochemicals. © 2024 Society of Chemical Industry.

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Recent advances in the natural products-based lead discovery for new agrochemicals

Zhang,

Duan,

Jin

et al. 2023

Advanced Agrochem

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Acaricidal and insecticidal efficacy of new esters derivatives of a natural coumarin osthole

Cited by 14 publications

References 30 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

Plant natural product‐based pesticides in crop protection: semi‐synthesis, mono‐crystal structures and agrochemical activities of osthole ester derivatives, and study of their toxicology against Tetranychus cinnabarinus (Boisduval)

Recent advances in the natural products-based lead discovery for new agrochemicals

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