A New Group of Plant-Derived Naphthoquinone Pesticides

A series of compounds with structures based on insecticidal/acaricidal naphthoquinones isolated from Calceolaria andina has been synthesised. A feature of the series is the lack of resistance shown by strains resistant to established classes of pesticides. The importance for activity of the tetra-substituted carbon atom in the side-chain, as observed in the natural products, has been investigated. In analogues with acyclic side-chains the position of the tetra-substituted carbon for optimum activity was dependent on the length of the side-chain. With cyclic side-chains, activity was dependent on the size of the ring, the number and position of the substituents therein. Activity of the compounds examined was particularly high against Bemisia tabaci and Tetranychus urticae in direct-contact tests, but was much lower than expected in leaf-dip tests. A partial improvement based on formulation has been demonstrated. © 1997 SCI     

Dehydro-alpha-lapachone isolated from Catalpa ovata stems: activity against plant pathogenic fungi

The methanol extract of stems of Catalpa ovata G Don exhibits potent in vivo antifungal activity against Magnaporthe grisea (Hebert) Barr (rice blast) on rice plants, Botrytis cinerea Pers ex Fr (tomato grey mould) and Phytophthora infestans (Mont) de Bary (tomato late blight) on tomato plants, Puccinia recondita Rob ex Desm (wheat leaf rust) on wheat plants and Blumeria graminis (DC) Speer f. sp. hordei Marchal (barley powdery mildew) on barley plants. An antifungal substance was isolated and identified as dehydro-alpha-lapachone from mass and nuclear magnetic resonance spectral data. It completely inhibited the mycelial growth of B. cinerea, Colletotrichum acutatum Simmonds, Colletotrichum gloeosporioides Simmonds, M. grisea and Pythium ultimum Trow over a range of 0.4-33.3 mg litre(-1). It also controlled the development of rice blast, tomato late blight, wheat leaf rust, barley powdery mildew and red pepper anthracnose (Colletotrichum coccodes (Wallr) S Hughes). The chemical was particularly effective in suppressing red pepper anthracnose by 95% at a concentration of 125 mg litre(-1).     

METI-acaricide resistance in Tetranychus urticae does not confer resistance to the naphthoquinones

The naphthoquinones and the METI group of compounds act on sites associated with mitochondrial respiration, but METI-resistant strains of two-spotted spider mite from Japan and the UK exhibited no cross-resistance to the naphthoquinones. The potential for developing commercial naphthoquinones therefore remains high.     

Effect of Botanical Insecticides on the Foraging and Feeding Behavior of the Coccinellid PredatorCryptolaemus montrouzieri

To investigate the effect of botanicals on the foraging behavior of the mealybug predatorCryptolaemus montrouzieri Mulsant, predator larvae and adults were exposed to leaves and the mealybugPlanococcus citri (Risso) treated with one of the following: a crude neem seed extract; a formulation of azadirachtin (Azatin EC®); a pyrethrum extract; and one of two naphthoquinones isolated fromCalceolaria andina Benth. (BTG 504 and BTG 505). All the botanicals influenced the foraging behavior ofC. montrouzieri, at one or more concentrations. Larval and adult foraging behavior was influenced most by BTG 504 and neem also affected larval behavior; the predators contacted fewer treated leaves and spent less time on treated than on untreated leaves. Larvae also consumed fewer mealybugs treated with BTG 504 and BTG 505 compared with untreated mealybugs.