Activity of 1,4-Benzoquinones Against Formosan Subterranean Termites (Coptotermes formosanus)

• Published in: Journal of agricultural and food chemistry Vol. 56; no. 11; pp. 4021 - 4026
• Main Authors: Mozaina, Kobaisy, Cantrell, Charles L, Mims, Amelia B, Lax, Alan R, Tellez, Maria R, Osbrink, Weste L. A
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 11-06-2008
• Subjects: 1,4-benzoquinones; Animals; antitermite activity; Benzoquinone; benzoquinones; Benzoquinones - chemistry; Bioactive Constituents; Coptotermes formosanus; Eating - drug effects; Insect Control - methods; insecticidal properties; Insecticides; Isoptera; Quantitative Structure-Activity Relationship; quantitative structure-activity relationships; Structure-Activity Relationship; termiticide; termiticides; antitermite activity; Benzoquinone; termiticide
• ISSN: 0021-8561; 1520-5118
• DOI: 10.1021/jf800331r

A large number of naturally occurring and synthetic benzoquinones were evaluated for activity against the Formosan subterranean termite, Coptotermes formosanus, with potential use in termite control. Among these bioactive naturally occurring benzoquinones are 2-methyl-5-isopropyl-1,4-benzoquinone, 2-methoxy-6-pentyl-1,4-benzoquinone, 2,3-dimethoxy-5-methyl-6-(3-methyl-2-butenyl)-1,4-benzoquinone, 2,3-dimethoxy-5,6-dimethyl-1,4-benzoquinone, and 2,3-dichloro-5,6-dimethyl-1,4-benzoquinone. All five of these compounds demonstrated 100% mortality against C. formosanus by day 11 at a concentration of 1% (wt/wt) or less. In general, benzoquinones with one or two hydrophobic groups on the 5 and/or 6 positions of the quinone ring along with one or two group(s) on the opposite side of the ring, at the 2 and/or 3 position, led to high rates of mortality against C. formosanus. Quantitative structure−activity relationship (QSAR) studies showed no correlation between lipophilicity (calculated log P) and mortality for the entire group of nonhalogenated benzoquinones. A correlation was observed between C-6 chain length and day 3 percent mortality for 2,3-dimethoxy-5-methyl-6-substituted aliphatic benzoquinones where short chain lengths resulted in higher mortality.