Quantitative structure-activity relationships of pyrethroid insecticides

The structure-activity relationships of two congeneric series of pyrethroid insecticides, the methylbenzyl (1RS)-cis,trans-chrysanthemates tested against Musca domestica (houseflies) and Phaedon cochleariae (mustard beetles), and the (E)-4-aryl-3-chlorobut-2-enyl chrysanthemates and their corresponding 2,2,3,3-tetramethylcyclo-propanecarboxylates tested against M. domestica only, have been examined using multiple regression analyses and substituent constants. With M. domestica, different optimum partition values (π) were indicated for knockdown and toxicity; with P. cochleariae, an optimum π value for toxicity, similar to that for M. domestica, was obtained 24 h after application, but at later times the more lipophilic compounds were more effective. For the methylbenzyl chrysanthemates, a steric constraint associated with 3,5-dimethyl substitution reduced toxicity approximately five-fold. The influence on toxicity of geometrical isomerism and electronic effects are briefly discussed. Differences between the required polarities for knockdown and toxicity are attributed to variations in the binding affinities of pyrethroid molecules at the sites of action.     

昆虫对拟除虫菊酯类杀虫剂的代谢抗性机制研究进展

随着拟除虫菊酯类杀虫剂在卫生和农业害虫防治中的广泛应用,昆虫对此类杀虫剂产生抗性的报道越来越多。目前已明确昆虫对拟除虫菊酯类杀虫剂的抗性机制包括表皮穿透率下降、靶标抗性以及代谢抗性,其中代谢抗性机制较为普遍,而且其与昆虫对多种杀虫剂的交互抗性关系密切。目前,随着基因组、转录组以及蛋白质组学等新技术的发展及应用,昆虫对拟除虫菊酯类杀虫剂的代谢抗性机制研究也取得了很多新进展。昆虫体内细胞色素P450酶（P450s）、羧酸酯酶（CarE）及谷胱甘肽S-转移酶（GSTs）等重要解毒酶系的改变均与昆虫对拟除虫菊酯类杀虫剂的代谢抗性有关,其中这3类解毒酶的活性及相关基因表达量的变化是昆虫对此类杀虫剂产生代谢抗性的主要原因。明确昆虫对拟除虫菊酯类杀虫剂的代谢抗性机制,对合理使用此类杀虫剂及延缓抗药性的产生均具有重要意义。本文在总结拟除虫菊酯类杀虫剂代谢路径及相关生物酶研究概况的基础上,综述了近年来有关昆虫对此类杀虫剂代谢抗性机制研究的主要进展。     

Metabolic chemistry of pyrethroid insecticides

This review of studies on 20 pyrethroids with nine different acid moieties and ten different alcohol moieties reveals a diversity of functional groups undergoing metabolism in mammals, insects, other organisms, and microsomal esterase and oxidase systems. Seventy-nine metabolites are identified from the cis-isomer of permethrin and transpermethrin but fewer from other pyrethroids examined in less detail. The sites and rates of metabolic attack on each pyrethroid depend on the organism or system. Metabolism of pyrethoids by esterase and oxidase action usually limits their toxicity to mammals more than to insects, thereby conferring useful selective toxicity properties.     

Structural aspects of the knockdown of pyrethroid

The polarities of pyrethroids and their performance as knockdown and killing agents against houseflies are discussed. The optimum polarity for knockdown is here shown to be greater than that needed for kill, probably because knockdown depends on relatively rapid penetration through the cuticle into the haemolymph and thence to the site of action.     

Resistance of Bemisia tabaci (Homoptera: Aleyrodidae) to insecticides in southern Spain with special reference to neonicotinoids

The tobacco whitefly, Bemisia tabaci Gennadius (Homoptera: Aleyrodidae) which occurs in various parts of the world, has developed a high degree of resistance against several chemical classes of insecticide, including organophosphates, carbamates, pyrethroids, insect growth regulators and chlorinated hydrocarbons. The present studies were done in order to monitor the susceptibility of whitefly populations in southern Spain to insecticides commonly used there. Systemic bioassays using Spanish field populations of B tabaci collected in 1994, 1996 and 1998 indicated an increase, albeit a slow one, in resistance to imidacloprid over this period. Comparative studies of other neonicotinoids using the same bioassay revealed a high degree of cross‐resistance to acetamiprid and thiamethoxam. Leaf‐dip bioassays with adult females from these populations revealed a high level of resistance to cyfluthrin, endosulfan, monocrotophos, methamidophos, and pymetrozine, each at 200 mg litre⁻¹. Buprofezin and pyriproxyfen were tested against second‐instar nymphs and eggs, respectively. Buprofezin also showed a lower efficacy against ESP‐98, a strain of B tabaci received from Almeria in 1998, but pyriproxyfen resistance was not obvious when tested against eggs of strain ESP‐98. Field trials in 1998 revealed good efficacy of imidacloprid in one farm in the Almeria region and two greenhouses in Murcia and Sevilla, but a loss of activity by imidacloprid in another farm in the Almeria region. Cross‐resistance between imidacloprid and thiamethoxam was also confirmed under field conditions. © 2000 Society of Chemical Industry     

The toxicity of mixtures of a pyrethroid with organophosphorus insecticides to Tetranychus urticae Koch

Laboratory studies of the cotoxicity of a pyrethroid insecticide, fenvalerate, and several organophosphorus insecticides against the two-spotted spider mite, Tetranychus urticae Koch, showed that a useful degree of potientation of toxicity occurred. The most effective combination of fenvalerate and azinphos-methyl was found to be a 1:1 ratio. Phosphates and phosphorodithioates in combination with fenvalerate were more toxic than phosphoromonothioates. The results suggest a practical method of improving the acaricidal activity of pyrethroid insecticides.     

RU-15525, a new pyrethroid with a very strong knockdown effect

(E)-5-Benzyl-3- furylmethyl (1-R),3-S)-2,2-dimethyl-3-(2,3,4,5-tetrahydro-2-oxothien-3-ylidenemethyl)cyclopropanecarboxylate or RU-15525 is a new pyrethroid. The action of this compound was tested on Musca domestica and Aedes aegypti and a very strong knockdown effect was observed in comparison with the knockdown effect of allethrin, bioallethrin and (S)-bioallethrin.     

Residues of synthetic pyrethroid insecticides on horticultural crops

Foliar applications of synthetic pyrethroids were made to several crops to determine residue levels at various intervals after application. On onions, residues of cypermethrin, permethrin and fenvalerate were negligible > 0.1 mg kg^?1, 7 days after application. On lettuce, residues of fenvalerate and permethrin were 0.8 mg kg^?1. On celery, residues of fenvalerate did not decline and ranged from 0.12 to 0.25 mg kg^?1 during the 14-day period. On green bush-beans, residues of permethrin and cypermethrin did not decline during the 14-day period and ranged from 0.1 to 0.6 mg kg^?1. By day 7, residues of cyfluthrin, cypermethrin, deltamethrin, fenvalerate and permethrin on strawberries were less than the acceptable maximum tolerance of 0.1 mg kg^?1 with the exception of cypermethrin, applied at the rate of 0.14 kg a.i. ha^?1 which gave a residue of 0.14 mg kg^?1.     

Structure-activity relationships in a group of azoles,with special reference to 1,3-dioxolan-2-ylmethyl derivatives

Substituted imidazoles and substituted 1,2,4-triazoles are active to varying degrees in the control of fungi pathogenic to plants, animals and man. The relationship between chemical structure and their antifungal activity, both in-vitro and in-vivo, is reviewed.     

Actions of pyrethroid insecticides on insect axonal sodium channels

The actions of pyrethroid insecticides were tested on isolated giant axons of the cockroach Periplaneta americana, using oil-gap, single-fibre recording techniques. Current-clamp and voltage-clamp experiments were used to determine the actions of pyrethroids on axonal membrane potentials and ionic currents. Treatment with deltamethrin at micromolar concentrations caused gradual depolarisation of the axon accompanied by a reduction in amplitude of the action potential. This depolarisation was enhanced by an increase in stimulation frequency. Other synthetic pyrethroids: 3,4,5,6-tetrahydrophthalimidomethyl (1RS)-cis-3-[(RS)-2,2-dimethylcyclopropyl]-2,2-dimethylcyclopropanecarboxylate, biopermethrin and its (1S)-enantiomer, (1R)-tetramethrin, S-bioallethrin, bioresmethrin and its (1S)-enantiomer, cismethrin, and 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate (RU-15525, ‘Kadethrin’) were investigated. The (1S)-enantiomers were inactive, but all the other pyrethroids tested, apart from deltamethrin, induced prolonged negative (depolarising) after-potentials. All the treatments with the active pyrethroids resulted in the appearance of a voltage and time-dependent ‘maintained’ sodium conductance. The duration of this ‘slow’ conductance varied considerably depending on the pyrethroid under test. Clearly, the effectiveness of pyrethroids on whole insects is not determined only by the degree to which they directly modify the properties of sodium channels. Nevertheless, voltage-clamp experiments on isolated axons readily permit direct comparison of the actions of different pyrethroids on the sodium channels of insect neurones.     

Resistance of Thrips tabaci to pyrethroid and organophosphorus insecticides in Ontario, Canada

Onion thrips, Thrips tabaci Lindeman, were collected from commercial onion fields in 2001, 2002 and 2003 to assess resistance to lambda-cyhalothrin, deltamethrin and diazinon. In 2001, six of eight adult populations were resistant to lambda-cyhalothrin, with resistance ratios (RR) ranging from 2 to 13.1 and four of these were also resistant to deltamethrin, with RR ranging from 19.3 to 120. Three of four adult populations were resistant to diazinon with RR ranging from 2.5 to 165.8. In 2002, four of seven nymphal populations and three of six adult populations were resistant to deltamethrin, with RR ranging from 4.3 to 72.5 and 9.4 to 839.2, respectively. Only one of six nymphal populations and one of five adult populations were resistant to diazinon, with RR of 5.6 and 2.3, respectively. In 2003 diagnostic dose bioassays, 15 of 16 onion thrips populations were resistant to lambda-cyhalothrin and all were resistant to deltamethrin. Eight of the 16 were resistant to diazinon. These results indicate that insecticide resistance is widespread in onion thrips in commercial onion fields in Ontario.     

Polyclonal and monoclonal antibodies specific to the chrysanthemic acid moiety of pyrethroid insecticides

Two polyclonal and two monoclonal antibodies raised against chrysanthemic acid (CAA) were prepared for ELISA of pyrethroid insecticides with the common CAA moiety. The monoclonal antibody KCA226 showed the highest reactivity towards allethrin among the antibodies in C-ELISA, although KCA226 was more sensitive to higher concentrations of methanol than the polyclonal antibodies in ELISA. KCA226 was reacted linearly with allethrin at concentrations ranging from 1 to 10 μg litre^-1 in 0·5% methanol and from 300 to 10000 μg litre^-1 in 30% methanol. KCA226 reacted specifically with the pyrethroid insecticides with the CAA moiety but was much less reactive with CAA itself. These results suggest that C-ELISA based on KCA226 is useful for the assay of pyrethroid residues with the common CAA moiety. © 1998 Society of Chemical Industry     

Chemotherapy of experimental toxoplasmosis with special reference to robenidine

Robenidine as an anticoccidial agent alone (in doses of 50 and 100 mg/kg) or in association with two other antiprotozoal compounds--pyrimethamine and sulfadoxine (in doses of 2.5 and 250 mg/kg, respectively) were tested in the treatment of chronically infected mice with an avirulent cyst-forming HF strain of Toxoplasma gondii. The efficacy of the used drugs was evaluated by the cysts number in the brains of treated mice versus control group, antibody level and viability of survived cysts by the consecutive infection of mice. According to these criteria none of the tested drugs alone or combined exhibited to be able to produce an effective cure of cyst-stage of toxoplasmosis in experimental mice.     

Alternaria leaf spot of cotton with special reference to Zimbabwe

Abstract

Leaf spots caused by Alternaria macrospora and A. alternata are common in cotton crops around the world. Both species are, however, usually considered to be minor pathogens of Upland cotton (Gossypium hirsutum) but A. macrospora causes premature defoliation with resulting yield loss in cultivars of G. barbadense in Israel and in the USA. A. macrospora is also able to cause defoliation in Upland cotton if the crop is. predisposed to infection by environmental or physiological stress. In Zimbabwe the main predisposing factor is potassium deficiency. The paper discusses the disease in Zimbabwe against the background of work reported from other countries on its effect on yield and on its epidemiology and control.     

Cotton whitefly (Bemisia tabaci) resistance to organophosphate and pyrethroid insecticides in Pakistan

Resistance to three organophosphate and four pyrethroid insecticides was monitored from 1992 to 2000 in field populations of adult whiteflies, Bemisia tabaci, from Pakistan using a leaf-dip method. There was generally a very high resistance to dimethoate and deltamethrin, and a moderate resistance to monocrotophos during 1992 to 1996. From 1997 to 2000, resistance to these insecticides dropped to low levels because of less reliance on them for whitefly control, and introduction of new chemistries with novel modes of action that had no cross-resistance to conventional insecticides. Concurrently, whitefly resistance to acephate, fenpropathrin, lambda-cyhalothrin and bifenthrin mostly remained low. An insecticide resistance management strategy is recommended that particularly emphasizes the rotation of still-effective insecticides from different chemical classes along with the use of novel chemicals and other tactics of integrated pest management.     

Charcoal rot in common bean with special reference to Kenya

Abstract

Charcoal rot caused by Macrophomina phaseolina (Deuteromycetes: Coelomycetes) is found throughout the tropics and subtropics and has a wide host range. Together with most of the legume crops, the common bean (Phaseolus vulgaris) Is a good host for the fungus which causes a range of symptoms, depending on environmental conditions and age of the plant. In addition to charcoal rot, which is a stem or stalk rot disease, the pathogen also causes damping‐off and seedling blight in beans. Charcoal rot in the mature plant is associated with senescence which is accelerated by water stress. The disease is most damaging in areas of unreliable rainfall and high temperature. In Kenya, beans are usually grown in mixed stands with maize, sorghum or millet. Population pressure has led to the cultivation of beans on land prone to drought. M. phaseolina is one of the most important pathogens affecting all the main crops of the farming systems in the semi‐arid areas of eastern Kenya and resistance to charcoal rot is a priority if beans are to be increasingly grown in these areas. The paper reviews the literature on charcoal rot of beans and on other crops where similar work has not been reported specifically for beans.     

Use and misuse of calorimetry with special reference to muscle physiology

Calorimetric experiments, on their own, can be extremely dangerous to biologists, for there are usually several possible, but alternative interpretations. The simplest interpretation is often not correct. The best way to use biological calorimetry on its own is to indicate good targets for biochemical investigations of a tissue. Even when biochemical investigations are carried out in parallel with calorimetry, dangers remain. In particular it is easy to assume that the heat observed is necessarily derived from the biochemical process measured. The way to avoid this error is to make an energy balance study. In most cases such a study requires calorimetric measurements on cell-free systems of known composition to establish ΔH values for in vivo conditions. Used in this way biological calorimetry is much more than a mere indicator that something is happening; it can lead to the most important statement about what is happening: that we do not yet understand it!     

Pathology of Pinus radiata in ecuador with special reference to Dothistroma

Abstract

Scirrhía pini Funk & Parker (Dothistroma septospora (Dorog.) Morelet) is reported for the first time from Ecuador. Dothistroma needle blight was recorded on Pinus radiata in both nurseries and plantations (2–9 years old), from various high altitude localities in the Sierra. Infection was particularly severe in plantations situated between 2500–3000 m a.s.l. Pinus patula showed a resistant reaction to the fungus as did some older P. radiata trees. Several associated fungi are also listed together with those facultative fungal pathogens isolated from necrotic needles and stem cankers.