Nematicidal activity of 3-acyltetramic acid analogues against pine wood nematode, Bursaphelenchus xylophilus
| Autor: | Seon-Mi Seo, Yong-Chul Jeong, Il-Kwon Park, Ji-Eun Lee, Hyo-Rim Lee, Sung-Chan Lee, Mark G. Moloney, Chan-Sik Jung |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Tylenchida
Surface Properties Substituent Pharmaceutical Science Bursaphelenchus xylophilus 010402 general chemistry 01 natural sciences Article Analytical Chemistry Polar surface area lcsh:QD241-441 chemistry.chemical_compound Structure-Activity Relationship lcsh:Organic chemistry Drug Discovery Botany lead compounds Structure–activity relationship Animals pine wood nematode Food science Physical and Theoretical Chemistry Wilt disease pine wilt disease toxicity 3-acyltetramic acid analogues biology Molecular Structure 010405 organic chemistry Antinematodal Agents Organic Chemistry biology.organism_classification Pinus Pyrrolidinones 0104 chemical sciences Partition coefficient Nematode chemistry Chemistry (miscellaneous) Pine wood Molecular Medicine |
| Zdroj: | Molecules, Vol 22, Iss 9, p 1568 (2017) Molecules; Volume 22; Issue 9; Pages: 1568 Molecules : A Journal of Synthetic Chemistry and Natural Product Chemistry |
| Popis: | Among 98 3-acyltetramic acid analogues, compounds 1c, 2c, 2f and 2g, showed >90% nematicidal activity against the pine wood nematode Bursaphelenchus xylophilus at a 10 μg/mL concentration. The nematicidal activities of compounds 1d, 1h, and 2k were a little lower at 88.0%, 85.8%, and 57.2% at a 10 μg/mL concentration, respectively. The nematicidal activity of emamection benzoate, widely used in Korea for the prevention of pine wilt disease, was 32.3% at a 10 μg/mL concentration. Other 3-acyltetramic acid analogues showed less than 30% nematicidal activity. A structure-activity relationship study indicated that the chain length of the C-acyl substituent was very important for high nematicidal activity. All active compounds had C13H27 or C11H23 acyl substituents, in two closely related groups with the common physicochemical properties of a polar surface area 57.6A2, PSA (polar surface area) 7.8–8.6% and ClogP (calculated partition coefficient) 5.1–5.9 and a polar surface area 75–84A2, PSA 11.1–11.6% and ClogP 4.7–5.1, respectively. Our study indicates that active 3-acyltetramic acid analogues could have potential as lead compounds for developing novel pine wood nematode control agents. |
| Databáze: | OpenAIRE |
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