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Molecules 2017, 22(9), 1568; doi:10.3390/molecules22091568

Nematicidal Activity of 3-Acyltetramic Acid Analogues Against Pine Wood Nematode, Bursaphelenchus xylophilus

1
Department of Forest Sciences, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Korea
2
Research Institute of Agriculture and Life Science, College of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Korea
3
Chemistry Research Laboratory, University of Oxford, Oxford OS1 3TA, UK
4
Division of Forest Insect Pests and Diseases, National Institute of Forest Science, Seoul 02455, Korea
*
Authors to whom correspondence should be addressed.
Received: 1 September 2017 / Revised: 13 September 2017 / Accepted: 15 September 2017 / Published: 18 September 2017
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Abstract

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. View Full-Text
Keywords: pine wilt disease; pine wood nematode; toxicity; lead compounds; 3-acyltetramic acid analogues pine wilt disease; pine wood nematode; toxicity; lead compounds; 3-acyltetramic acid analogues
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MDPI and ACS Style

Lee, H.-R.; Lee, S.-C.; Lee, J.-E.; Seo, S.-M.; Jeong, Y.-C.; Jung, C.-S.; Moloney, M.G.; Park, I.-K. Nematicidal Activity of 3-Acyltetramic Acid Analogues Against Pine Wood Nematode, Bursaphelenchus xylophilus. Molecules 2017, 22, 1568.

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