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

Abstract

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.

Fungal biosynthesis of the bibenzoquinone oosporein to evade insect immunity

“…Although 1,4-benzoquinones cause 100% mortality in subterranean termites (39), topical application of oosporein on the sap-sucking whitefly indicated that the use of toxin alone resulted in ∼20% insect mortality, and the use of the fungal spores alone led to ∼60% mortality. However, the percentage of insect death increased to 92% when the fungal spores were used in combination with the red pigment (16).…”

Recent advances in 1,4-benzoquinone chemistry

“…The antitermite activity of selected naturally occurring and synthetic 1,4-benzoquinones have been reported by Mozaina et al 37 They evaluated a set of chosen benzoquinones for activity against the Formosan subterranean termite, Coptotermes formosanus and showed that five bioactive naturally occurring 1,4-benzoquinones (4, 7-10) demonstrated 100% mortality against C. formosanus.…”

“…Another important 2,5-dihydroxy-3-alkyl-1,4-benzoquinone is embelin (2,5-dihydroxy-3-undecyl-1,4-benzoquinone) (37) which is a major constituent in the extracts of various parts of the shrub Embelia ribes. Embelin is reported to elicit a wide range of biological effects including anti-helmintic, analgesic, antifertility, antitumor and antioxidant properties.…”

“…58 Recently an unusual N-containing benzoquinone derivative was isolated from the roots of Embelia ribes by Lin et al 59 and assigned the structure N-(3-carboxypropyl)-5-amino-2-hydroxy-3-tridecyl-1,4-benzoquinone, 38. It shares the long unbranched 3-alkyl side chain of embelin (37) although it has two extra carbons and has the unusual incorporation of g-aminobutyric acid linked to the quinone through the nitrogen. Compound 38 has the distinction of first naturally occurring nitrogen containing 2,5-dihydroxy-3-alkyl-1,4-benzoquinone derivative.…”

Antitermite Activities of Coumarin Derivatives and Scopoletin from Protium javanicum Burm. f.

“…Among the many species, Coptotermes formosanus Shiraki is the subterranean termite responsible for major destruction of wooden materials in countries such as Japan, and Taiwan, and the southern parts of the United States. For this reason, Coptotermes formosanus Shiraki has been bioassayed in many research studies (Chang and Cheng 2002;Zhu et al 2003;Cheng et al 2007;Katsumata et al 2007; Mozaina et al 2008).…”