Laboratory evaluation of fipronil,a phenylpyrazole insecticide,against adult Anopheles (Diptera: Culicidae) and investigation of its possible cross‐resistance with dieldrin in Anopheles stephensi

Adult mosquitoes from two strains of Anopheles gambiae and from three strains of Anopheles stephensi were exposed to 0.25% fipronil‐treated papers in WHO test kits or to 500 mg fipronil m⁻² impregnated mosquito netting in bioassay spheres. For comparison, tests were also carried out with the pyrethroid permethrin, using the same methods and doses, and on papers treated with 0.4 and 4% of the cyclodiene insecticide dieldrin. Compared with the same doses of permethrin, fipronil showed less and delayed activity. Two of the An stephensi strains were resistant to fipronil and dieldrin. To investigate whether this was due to a resistance mechanism in the An stephensi strains acting against both insecticides, the most fipronil‐ and dieldrin‐tolerant strain was further selected in two separate lines with one of the insecticides, followed by tests with the insecticide that the line had not been selected with. This indicated a concomitant rise of resistance to dieldrin in the fipronil‐selected line and vice versa. Repeated back‐crossing of the two lines with a susceptible strain and re‐selection with either dieldrin or fipronil gave evidence for the involvement of a single resistance mechanism to both insecticides. Permethrin resistance in both lines declined with selection for dieldrin or fipronil and confirms the absence of cross‐resistance between fipronil and pyrethroids. © 2001 Society of Chemical Industry     

Insect epoxide hydrolase: Properties of a purified enzyme from the southern armyworm (Spodoptera eridania)

An epoxide hydrolase purified from midgut microsomes of southern armyworm (Spodoptera eridania) larvae exhibited high activity toward monosubstituted epoxides (1,2-epoxyoctane, 1,2-epoxypropane, and styrene oxide) and lower activity toward cis-1,2-disubstituted epoxides (cyclohexene oxide, and the cyclodienes HEOM, HCE, and chlordene epoxide). Trisubstituted epoxides (2-methyl-2,3-epoxyheptane and JH-1) as well as several cyclodiene insecticides (dieldrin, endrin, endo-epoxyaldrin, and anti-heptachlor epoxide) were refractory to enzymatic attack. It is concluded that both lipophilic and steric factors dictate the substrate specificity of the enzyme. With cyclohexene oxide the enzyme yields the 1R, 2R enantiomer of the trans-diol. The purified enzyme is inhibited by several epoxides and mixed-function oxidase inhibitors and the potency of 3,3,3-trichloro-1,2-epoxypropane and sodium picrylsulfonate suggest the importance of electronic factors in the inhibitory mechanism. Studies with specific amino acid modifiers suggest the presence of an essential lysine or histidine residue at the active site and indicate that the enzyme lacks a metal ion requirement and an essential cysteine residue. The purified enzyme has a molecular weight of 46,000 daltons and amino acid analysis and immunochemical studies show it to be very similar to, but not identical with, the epoxide hydrolase from mammalian liver microsomes.     

Toxicity of insecticides to the tsetse fly,Glossina palpalis palpalis in Nigeria and comparison of tolerances in 1974–1975 and 1979–1982

Abstract

Toxicities o1 12 chemical insecticides to wild‐caught tsetse flies, Glossina palpalis palpalis in Nigeria were measured by topical application. Median lethal doses (as ng per fly) at 48 h after application for older flies, males (females), were: DDT 331 (700), dieldrin 14 (46), endosulfan 8 (15), malathion 193 (273), fenitrothion 47, pirimiphos methyl 31 (45), tetrachlorvinphos 14 (33), sumicidin 28 (58), neopynamin 12 (15), sumithrin 10 (8), permethrin 4.4 (5.9), deltamethrin 0.45 (0.94). Lethality expressed as dose per whole fly can be termed effective toxicity/tolerance and those expressed as dose per weight unit of fly can be termed intrinsic (or true) toxicity/tolerance. Generally, effective tolerance was greater for females than males, especially for older flies. However, intrinsic tolerance was often about equal for the sexes or greater for males. Regardless of sex, effective tolerance increased with increasing fly age and intrinsic tolerance increased during later ageing but not during early ageing. This suggested that protecting mechanisms developed during ageing. Flies fed a few hours before treatment in 1979–1982 were more tolerant of three organochlorines and three organophosphates than flies fed the day before treatment in 1974–1975, probably due to diversion of poisons from sites of action into inert undigested blood. However, results and statistical analysis suggested a slight increase in true tolerance of males to DDT during the intervening years. Continued monitoring of tolerance in the fly populations is recommended.     

Toxicity of Mixtures of Bacillus thuringiensis with Endosulfan and Other Insecticides to the Cotton Boll Worm Helicoverpa armigera

In the laboratory, low concentrations of Bacillus thuringiensis Berliner (B.t.), as ‘Dipel’ 2X applied (at about the LC₅) to cotton leaves enhanced the activity of endosulfan and reduced resistance to endosulfan from approximately seven fold to two fold in neonate larvae of Helicoverpa armigera (Hubner). Low (LC₅) concentrations of endosulfan also increased the toxicity of B.t. Both endo-sulfan and B.t. increased the toxicity of the stomach poison cryolite to H. armigera. This increased toxicity was not observed where B.t./endosulfan combinations were applied topically to larvae or where B.t. was combined with organophosphorus or pyrethroid insecticides which are considered primarily to be contact toxicants. Mixtures of B.t. and endosulfan applied at equitoxic concentrations were less toxic than similar concentrations applied alone.     

Sub-lethal influences of different insecticides on oviposition preference of Helicoverpa armigera (Hübner) (Lepidoptera: Noctuidae) on cotton in relation to altered plant morphology

We investigated the sub-lethal influences of spinosad, chlorpyriphos, endosulfan, acephate and cypermethrin on the oviposition responses of Helicoverpa armigera (Hübner) to cotton plants, under cage and laboratory conditions. The rank order of toxicity (LC₅₀ values as a per cent) of test insecticides against third instar larvae using the leaf disc method was: spinosad > chlorpyriphos > endosulfan > acephate > cypermethrin. On whole plants, females laid more eggs on acephate LC₅₀-, acephate LC₃₀- and cypermethrin LC₅₀-treated cotton plants than on the control. The chlorpyriphos-treated plants were least preferred for oviposition. When excised cotton leaves from different treatments were used in a multiple-choice test, cypermethrin LC₅₀- and endosulfan LC₃₀-treated leaves received more eggs than the control. The repeated application of sub-lethal concentrations of different insecticides reduced plant height in the case of acephate LC₃₀ and cypermethrin LC₅₀, while plant spread and upper canopy leaf area were reduced in both treatments of acephate and cypermethrin. Reduced plant spread, upper canopy leaf area followed by plant height were found associated with oviposition preference by H. armigera females.     

Toxicity of spinosad to susceptible and resistant strains of house flies,Musca domestica

The toxicity of spinosad, a new insecticide derived from the bacterium Saccharopolyspora spinosa, was evaluated against susceptible and resistant strains of house fly (Musca domestica L.). Spinosad was highly toxic to house flies based on 72-h LD₅₀ values and the symptoms of poisoning were consistent with a neurotoxic mechanism of action. Spinosad was relatively slow acting, with the maximum toxicity noted at 72 h. Piperonyl butoxide and S,S,S,-tribu-tylphosphorotrithioate synergized the toxicity of spinosad by 3·0- and 1·8-fold, respectively, while diethyl maleate had no significant effect. These results suggest that there is a small degree of monooxygenase-mediated spinosad detoxification in house flies, while hydrolases may be only minimally important and glutathione transferases may have no role. There were no substantial levels of cross-resistance detected, except in the LPR strain where a low 4·3-fold cross-resistance was observed. The cyclodiene-resistant OCR strain was 2·7-fold more sensitive to spinosad than the susceptible strain (CS). These results suggest that cross-resistance may not be a limiting factor for the use of spinosad against house flies. © 1998 Society of Chemical Industry     

The antifungal activity of some sulphonyl derivatives of isoxazole,pyrazole, thiazole and thiophene

Fifty-three heterocyclic sulphonyl derivatives including eight sulphonamides, three sulphonyl azides, nine sulphonohydrazides and twenty sulphonohydrazones of substituted thiophenes, and a smaller range of analogous isoxazoles pryazoles and thiazoles, were tested as potential fungicides in a simple screening procedure against Mucor mucedo, Septoria nodorum, Trichoderma viride, Chaetomium globosum and Aspergillus niger. Several thiophene-2-sulphonyl based compounds exhibited a high level of antifungal activity at 100 mg litre^?1 against the five test species, especially the mono-halogen-substituted sulphonamides and sulphonohydrazines, in which a single chlorine or bromine atom was substituted in the para position of an attached phenyl ring. The most active compound, against all five species of fungus was N-(4-chlorophenyl)-N-(trichloromethylthio) thiophene-2-sulphonamide which had average MIC₅₀ and MIC₁₀₀ values of 86 and 180 μmol respectively. (MIC₅₀ and MIC₁₀₀ values are, respectively, the concentrations required to inhibit fungal growth by 50% and to inhibit it totally.) In general, the isoxazole analogues of the thiophene-2-sulphonyl compounds exhibited a much lower fungitoxic activity, whilst the pyrazole and thiazole based compounds had little or no activity. Compared with the other results, the considerable activity shown by 4-[2′-(3,4-dichlorobenzylidene)hydrazinosulphonyl]thiophene-2-carboxylic acid was unexpected.     

Phytotoxic activity of norbornane and nortricyclene lactones

A series of bromo-, hydroxy- and keto-derivatives of norbornane-6-hydroxy-2-carboxylic acid, y-lactone and some related compounds have been prepared and examined for phytotoxic activity. The 3-exo-propionyl, and 3-exo-5-exo-dibromo substituted compounds have been found to have the greatest activity.     

Toxicity of some pyrethroids to the adult desert locust,Schistocerca gregaria forsk

The toxicity of a number of topically applied pyrethroids has been tested against adult male desert locusts, Schistocerca gregaria: the most potent proved to be 5-benzyl-3-furylmethyl (+)-trans-chrysanthemate (bioresmethrin) with a weighted mean LD₅₀ of 4.0 μg/g. The remaining compounds may be ranked in order of toxicity as follows: 5-benzyl-3-furylmethyl (±)-cis-trans-chrysanthemate (resmethrin) > 4-allyl-2,6-dimethyl-benzyl(+)-trans-chrysanthemate > 4-allylbenzyl (+)-trans-chrysanthemate > 2,4,6-trimethylbenzyl (+)-cis-trans-chrysanthemate > 2,3,4-trimethylbenzyl (+)-cis-trans-chrysanthemate > 2,4-dimethylbenzyl (±)-cis-trans-chrysanthemate; 2-methylbenzyl (±)-cis-trans-chrysanthemate. A small factor of synergism (4.2) was obtained with bioresmethrin following pre-treatment with sesamex, but with resmethrin the synergistic ratio (1.6) was of little practical significance.     

Heterocyclic Insecticides Acting at the GABA-Gated Chloride Channel: 5-Alkyl-2-arylpyrimidines and -1,3-thiazines

5-tert-Butyl-2-(4-ethynylphenyl)pyrimidine and the corresponding 2,5-disubstituted-4H-1,3-thiazine block the GABA-gated chloride channel at c.20and c.200 nm , respectively, measured as 50% inhibition of the binding of 1-(4-ethynylphenyl)-4-[³H]propyl-2,6,7-trioxabicyclo[2.2.2]octane (4′-ethynyl-4-n-[³H]propylbicycloorthobenzoate; [³H]EBOB) in house fly and mouse brain membranes, and they are also toxic to topically-treated flies with LD₅₀ values of 6–27 μg g⁻¹ alone and 2–6 μg g⁻¹ with piperonyl butoxide (PB) as synergist. In the pyrimidine series, the general pattern of effectiveness of substituents in the 5-position is tert-butyl>isopropyl≈cyclohexyl≈cyclopropyl>methyl, phenyl and 3- and 4-fluorophenyl, and in the 2-position is 4-ethynylphenyl≪4-bromophenyl. These planar pyrimidines and nearly-planar 4H-1,3-thiazines with 2-ethynylphenyl or 2-bromophenyl and 5-tert-butyl or 5-isopropyl substituents are more effective than the corresponding 6H-1,3-thiazine, 6-oxo-1,3-thiazines and 4,6-dioxo-1,3-thiazine examined, but they are less active than the analogous conformationally flexible trans-1,3-dioxanes and -1,3-dithianes. The heterocyclic moiety confers a region of high electron density and positions the 2- and 5-substituents in a linear or parallel relationship for optimal affinity at the receptor. Two observations indicate that the new pyrimidines and thiazines probably act as chloride channel blockers. First, the poisoning signs are identical to those of EBOB in both mice and house flies. Second, each of the pyrimidines, thiazines and dioxanes falls on the same correlation line for inhibition of [³H]EBOB binding and toxicity to house flies (with PB) as that obtained earlier for EBOB analogs, dithianes and polychlorocycloalkanes, suggesting that they all act at the same or closely coupled binding sites in the GABA-gated chloride channel.     

The fungicidal activity of substituted 1,4-naphthoquinones. Part III: Amino,anilino and acylamino derivatives

A variety of 2-amino-, 2-anilino- and 2-acylamino-1, 4-naphthoquinones, with hydrogen, chlorine, alkoxy, phenoxy, methylthio or phenylthio as the 3-substituent, have been synthesised and assayed against Botrytis cinerea, Cladosporium fulvum and Venturia inaequalis. With few exceptions, only the 2-acylamino compounds possessed appreciable fungicidal activity: this was of a high order in the cases of 2-prop-ionamido-, 2-N-methylacetamido-3-methylthio-, and 3-methoxy-2-N-methylacetamido-1, 4-naphthoquinones.     

Characterization of an endopolygalacturonase Gene cppg1 from Phytopathogenic Fungus Chondrostereum purpureum

Chondrostereum purpureum, a phytopathogenic fungus, produces endopolygalacturonase (endoPG) which has been suggested to have a causal role in the silver-leaf symptom of apple trees. In this paper, we detected C. purpureurn-derived endoPG at the infection sites using ELISA with a polyclonal antibody against endoPG I. A gene encoding endoPG I and its homolog were also isolated from the C. purpureum genome. The endoPG I gene was designated as cppg1. The cppg1 gene is the first fungal endoPG gene reported in the Basidiomycetes. Received 31 May 2000/ Accepted in revised form 13 September 2000     

Insecticidal potency of novel compounds on multiple insect species of medical and veterinary importance

BACKGROUND: Vector‐borne diseases continue to present significant threats to human, animal and plant health. Mosquitoes, houseflies, sand flies and stable flies are well‐known vectors of several human and animal pathogens. The toxicity of selected semiochemicals with molecular structures indicative of insecticidal activity was determined against these insect species with the aim of developing novel insecticides toxic to multiple insect species. RESULTS: Three semiochemicals, namely beta‐damascone, cyclemone A and melafleur, showed remarkable toxicity to three mosquitoes, Aedes aegypti L., Ae. albopictus (Skuse) and Anopheles quadrimaculatus Say, the housefly, Musca domestica L., the stable fly, Stomoxys calcitrans L., and the sand fly, Lutzomyia shannoni (Dyar). The chemicals were equally toxic to several field‐collected permethrin‐tolerant housefly strains. When formulated as 500 mL L^?1 emulsifiable concentrates, the chemicals demonstrated stability and toxicity on filter paper and camouflage military fabrics, with persistence up to 8 days under laboratory conditions. The chemicals were equally effective under field conditions when evaluated on unpainted plywood panels, although a higher dosage was required under field conditions to achieve similar efficacy. CONCLUSION: Laboratory quantification of LC₅₀ values and field efficacy of three semiochemicals as formulated compounds on mosquitoes, houseflies, stable flies and sand flies showed that these semiochemicals could serve as potent insecticides for multiple insect species. Copyright © 2010 Society of Chemical Industry     

Lethal and sublethal effects of chlorantraniliprole on three species of Rhagoletis fruit flies (Diptera: Tephritidae)

BACKGROUND: Chlorantraniliprole formulated as a 350 g kg^?1 WG (Altacor 35WG) for management of apple maggot Rhagoletis pomonella (Walsh), blueberry maggot R. mendax Curran and cherry fruit fly R. cingulata (Loew) (Diptera: Tephritidae) was evaluated in laboratory assays and field trials. RESULTS: A tarsal contact toxicity bioassay showed that a surface residue of 500 mg L^?1 of chlorantraniliprole caused significantly higher mortality of male and female flies of all species compared with a control. Male apple maggot and blueberry maggot mortality was significantly higher than that for females, but there was similar mortality of male and female cherry fruit flies. An ingestion toxicity bioassay showed that 500 mg L^?1 of chlorantraniliprole in diet caused significantly higher mortality of male and female flies of all species than the control, but there were no significant differences among the sexes. Delayed egglaying by females that had ingested chlorantraniliprole was found, but there were no significant sublethal effects on either the number of eggs laid or the egg hatch. Field trials with apple maggot and cherry fruit fly showed that protection of fruit by chlorantraniliprole was comparable with that of standard broad‐spectrum insecticides. CONCLUSIONS: The present data indicate that chlorantraniliprole has suppressant activity against Rhagoletis fruit flies, preventing fruit infestation primarily through direct lethal effects. Copyright © 2008 Society of Chemical Industry     

Selection of Anopheles stephensi with DDT and dieldrin and cross-resistance spectrum to pyrethroids and fipronil

The field strain of Anopheles stephensi, the main malaria vector in south of Iran, was colonized in laboratory and selected with DDT and dieldrin in two separate lines for 3 generations to a level of 19.5- and 14-fold for DDT and dieldrin resistance, respectively. Synergist tests with chlorofenethol (DMC) and piperonyl butoxide (PBO) on the selected strains indicated that dehydrochlorination and oxidative detoxification might be the underlying mechanisms involved in the resistance to dieldrin and DDT in selected strains. DDT selection decreased susceptibility to DDT and pyrethroids including lambdacyhalothrin, permethrin deltamethrin and cyfluthrin. The result also showed that selection with dieldrin caused negative and positive cross-resistance to pyrethroid and fipronil, respectively. Based on these results, it can be concluded that besides metabolic resistance mechanisms, other factors such as mutation in γ aminobutyric acid (GABA) and voltage-gated sodium channels (Kdr) might be involved.     

PCR-based differentiation of Fusarium oxysporum ff. sp. lycopersici and radicis-lycopersici and races of F. oxysporum f. sp. lycopersici

The pathogenic type (form and race) of Fusarium oxysporum, which generates wilt symptoms on tomato, was rapidly identified with a polymerase chain reaction (PCR)-based technique. We compared the partial nucleotide sequences of endo polygalacturonase (pg1) and exo polygalacturonase (pgx4) genes from isolates of F. oxysporum ff. sp. lycopersici (FOL) and radicis-lycopersici (FORL) from Japan and designed specific primer sets (uni, sp13, sp23, and sprl) based on the nucleotide differences that appeared among the pathogenic types. PCR with the uni primer set amplified a 670∼672-bp fragment from all isolates of FOL and FORL. With the sp13 primer set, an amplicon of 445 bp was obtained only from isolates of FOL race 1 and 3. With the sp23 primer set, a 518-bp fragment was obtained from isolates of FOL race 2 and 3. The sprl primer set yielded a 947-bp fragment from isolates of FORL, but not from FOL. A combination of amplifications with these primer sets effectively differentiated the pathogenic types of F. oxysporum in tomato.     

Second International Symposium of the European Weed Research Society,Uppsala, August 1977

Abstract

The results of a discriminative spray application of decamethrin from a helicopter to fringing forest habitats of Glossina tachinoides in the Komoe valley, Upper Volta, are described. The insecticide formulated as a 2.5% emulsion concentrate was diluted with river water and applied from a Bell 47G-4A helicopter to the fringing forests of a 14 km long stretch of the River Komoe at a dosage of 12.5 g a.i./ha. The insecticide application equipment was so adjusted that when the helicopter was flown at 30 km/h, the effective swath width was about 30 m and the vmd of emitted spray was c.150 μm. Insecticide swaths were applied to the inner edges of fringing forests that were up to 100 m wide. Forests wider than 100 m received an additional insecticide swath.

The experimental area was protected from reinvasion by the establishment of dieldrin barriers at its extremities and along some tributaries and woodland/floodplain ecotones. The dieldrin was applied by the same method as was used to apply the decamethrin. The single discriminative application of decamethrin was extremely effective in controlling G. tachinoides for a period of at least 38 days, at the end of which time the wet season had commenced and there was evidence that flies were entering the experimental area from nearby unsprayed areas. The authors discuss the possible practical applications of the technique and make suggestions on how it might possibly be refined in order to reduce undesirable river water contamination and operational costs. The authors draw attention to the need for field trials, such as that reported upon, to be conducted on a sufficiently large scale and for the experimental areas to be well protected against reinvasion, if meaningful evaluation data are to be obtained.     

The effect of topical and injected olive oil on knockdown by DDT,dieldrin, methyl parathion,and dimethoate in Musca domestica

Houseflies were pretreated with olive oil by two methods, topical application or injection, then exposed to residues of DDT, dieldrin, methyl parathion, or dimethoate. Knockdown was recorded for normal and pretreated flies. Knockdown rates of pretreated flies were significantly different (generally lower) from normal flies in practically all cases. Protection against knockdown was positively correlated with olive oil-water partition coefficients of the insecticides. The effect of dosage on the degree of protection was investigated with DDT. These data support the possibility that hemolymph distributes insecticides throughout the body in exposed insects.     

The Pyrethrins and Related Compounds. Part XLI. Structure–Activity Relationships in Non-ester Pyrethroids against Resistant Strains of Housefly (Musca domestica L.)

A series of pyrethroids, related to NRDC 200 and etofenprox (MTI500) in which the central region is represented by a non-ester link, have been tested against one susceptible and two resistant strains (kdr and super-kdr) of houseflies (Musca domestica L.). A range of structural variations in the central region have been examined. Resistance factors mostly fell within narrow ranges for both resistant strains i.e. 10–50-fold resistance against kdr and 50–150-fold against super-kdr; thus no correlation of resistance with structural features was detectable for this region. Other changes examined were the substituent on the phenyl ring in the ‘acid’ component and the bridging group in the ‘alcohol’ component where small variations in response were observed. Examination of the effect of varying the ‘alcohol’ side chain was limited by lack of active analogues.     

The effects of dieldrin and isomeric aldrin diols on synaptic transmission in the American cockroach and their relevance to the dieldrin poisoning syndrome

Dieldrin and two of its metabolites, 6,7-trans-dihydroaldrindiol, and 6,7-cis-dihydroaldrindiol, were studied with regard to their toxicity to the American cockroach, effects on ganglia of the ventral nerve cord, and penetration into the ventral nerve cord of poisoned cockroaches. An approximate LD₅₀ for injected doses of dieldrin was 0.45 mg/kg. After injection at 115 mg/kg, the trans isomer of aldrin diol caused about 70%, and the cis isomer about 50% mortality. Injected doses of 40 mg/kg of the three compounds appeared in the ventral nerve cord to the extent of 0.13–0.26% of the doses. Dieldrin was more potent, but slower acting than the diols in causing synaptic after-discharge and elevated spontaneous activity in isolated nerve cords. The results are discussed in relation to other studies on these compounds. It was concluded that, in the American cockroach, dieldrin, rather than either of the diols, is the insecticidal agent in dieldrin poisoning, and that metabolic conversion of dieldrin to the cis and/or trans aldrindiol constitutes a detoxification.