Synthetic Pyrethroid Bifenthrin Research Articles

Synthesis, antimosquito activities, photodegradation, and toxic assessment of novel pyrethroids containing 2-chlorobiphenyl and 2-chlorophenylpyridine.

Aedes albopictus is a mosquito species and a vector of dengue virus and malaria parasites that represents a significant threat to global public health. Although mosquito populations have been effectively controlled through the use of synthetic insecticides, the emergence of widespread insecticide resistance in wild mosquito populations is a strong motivation to explore new insecticidal chemistries. In this study, A. albopictus was treated with a series of novel pyrethroids containing 2-chlorobiphenyl and 2-chlorophenylpyridine via topical application. The relative antimosquito activity of each novel compound was determined, as measured by the LC50 , and compared with the synthetic pyrethroid bifenthrin. The most antimosquito activity compound (SZ-B-11) was 4.69 times more active than bifenthrin. The novel compounds were also sensitive to wild A. albopictus. In addition, in silico toxicity assessment of aquatic organisms showed that the acute toxicity and chronic toxicity of SZ-B-11 were 31.96 times and 934.40 times lower than those of bifenthrin, respectively. Cytotoxicity assessment demonstrated that all tested compounds were nontoxic against SH-SY5Y cell lines. Furthermore, photolytic results suggested that SZ-B-11 would be photodegraded more easily than bifenthrin and would reduce secondary pollution. Novel pyrethroids containing 2-chlorobiphenyl and 2-chlorophenylpyridine, through simple synthesis steps, have better antimosquito activity, low resistance, less ecotoxicity, readily degradable characteristics, and may reduce secondary pollution. They are promising insecticides with potential application prospects in agricultural production and environmental protection. © 2021 Society of Chemical Industry.

Field evaluation of water plant extracts on sucking insect pests and their associated predators in transgenic Bt cotton

Several plant species and their compounds are well-known to have some pesticidal properties against a wide range of insect pests. Potential of two water plant extracts, Azadirachta indica A. Juss and Melia azedarach L., in comparison with the synthetic pyrethroid bifenthrin against sucking insect pests and their associated predators, as well on the yield in Bt cotton, was evaluated. The population of the sucking insect pests was found lowest in the positive control (only bifenthrin application). The A. indica extract reduced the pest population equivalent to the positive control, but the highest populations were observed in both negative controls (only water and 0.1% soap with water application). The M. azedarach did not show any harmful effect on the insect population. The predators’ abundance was higher in the plots where botanicals were applied, while the lowest population was observed in the bifenthrin treatment. In comparison to the negative control (only water application), (63.4%) cotton yield was increased by the application of A. indica and (58.8%) by the application of the synthetic insecticide. Using plant extracts of A. indica to control sucking insect pests of cotton can be as effective as synthetic insecticides in terms of crop yield beside they are safer for natural enemies in the field.

Effects of polyethylene microplastics on the acute toxicity of a synthetic pyrethroid to midge larvae (Chironomus tepperi) in synthetic and river water

Microplastics are ubiquitous pollutants in the aquatic environment. However, our understanding of the interaction of chemicals, particularly synthetic pyrethroids, with microplastics and the potential toxic effects of sorbed contaminants on aquatic organisms under realistic conditions is still extremely limited. In this study, we examined whether the presence of polyethylene (PE) microplastics can affect the acute toxicity of the synthetic pyrethroid bifenthrin to an invertebrate Chironomus tepperi in both synthetic and river water. Bifenthrin alone was, as expected, acutely toxic to exposed larvae (LC50 of 0.5 μg/L after 48 h exposure). The addition of microplastics to synthetic water significantly reduced the toxicity of bifenthrin (apparent LC50 = 1.3 μg/L), most likely because sorption of bifenthrin to microplastics reduced its bioavailability to the exposed larvae. A sorption capacity experiment showed that >92% of bifenthrin was sorbed to microplastics. In river water containing 9.6 mg/L organic carbon, bifenthrin alone was less toxic (LC50 = 1.3 μg/L) than in synthetic water. Strikingly, the addition of microplastics to river water did not mitigate bifenthrin toxicity (apparent LC50 = 1.4 μg/L), most likely due to greater interaction of bifenthrin with organic carbon than with microplastics. While PE microplastics reduced the negative effects of bifenthrin in synthetic water, the presence of organic carbon in river water without microplastics also reduced toxicity. This suggests that while sorption of contaminants to microplastics does occur, it may not be as relevant under environmentally realistic conditions with mg/L concentrations of organic matter.

Toxicant mixtures in sediment alter gene expression in the cysteine metabolism of Chironomus tepperi.

Sediment contamination can pose risks to the environment, and sediment toxicity tests have been developed to isolate the impact of sediment from other factors. Mixtures of contaminants often occur in sediments, and traditional endpoints used in toxicity testing, such as growth, reproduction, and survival, cannot discern the cause of toxicity from chemical mixtures because of complex interactions. In urban waterways, the synthetic pyrethroid bifenthrin and the metal copper are commonly found in mixtures, so the present study was designed to investigate how these contaminants cause toxicity in mixtures. To investigate this, Chironomus tepperi was exposed to environmentally relevant concentrations of copper and bifenthrin-spiked sediments in a 2-way factorial mixture for 5 d. Growth and expression profiles of cysteine metabolism genes were measured after exposure. Growth increased at low copper concentrations, decreased at high copper concentrations, and was unaffected by bifenthrin exposures. Copper exposures induced possible cellular repair by upregulating S-adenosylmethionine synthetase expression and downregulating expression of S-adenosylhomocysteine hydrolase and cystathionine-β-synthase. Metallothionein upregulation was also observed. Bifenthrin exposure altered cysteine metabolism to a lesser extent, downregulating cystathionine-β-synthase and γ-glutamylcysteine synthase. Synergistic, antagonistic, and dose-dependent interactions were observed, and there was evidence of conflicting modes of action and limited substrate production. These findings demonstrate how contextual gene expression changes can be sensitive and specific identifiers of toxicant exposure in mixtures. Environ Toxicol Chem 2017;36:691-698. © 2016 SETAC.

Changes in gene transcription and whole organism responses in larval fathead minnow ( Pimephales promelas) following short-term exposure to the synthetic pyrethroid bifenthrin

The combination of molecular and whole-organism endpoints in ecotoxicology provides valuable information about the ecological relevance of sublethal stressor effects in aquatic ecosystems such as those caused by the use of insecticides and translocation of their residues into surface waters. This study contributes knowledge about the sublethal effects of a common use insecticide, the synthetic pyrethroid bifenthrin, on larval fathead minnow ( Pimephales promelas). Transcriptomic responses, assessed by quantitative real-time PCR, combined with individual effects on swimming performance were used to estimate the ecological relevance of insecticide impacts. Significant transcriptomic responses were observed at 0.07 μg L −1 bifenthrin (lowest observed effect concentration, LOEC) but mostly followed a biphasic rather than a linear dose–response with increasing concentration. Transcript patterns for genes involved in detoxification, neuromuscular function and energy metabolism were linked to an impairment of swimming performance at ≥0.14 μg L −1 bifenthrin. With increasing treatment concentration, a significant down-regulation was observed for genes coding for cyp3a, aspartoacylase, and creatine kinase, whereas metallothionein was up-regulated. Additionally, bifenthrin induced endocrine responses as evident from a significant up-regulation of vitellogenin and down-regulation of insuline-like growth factor transcripts. Recovery occurred after 6 days and was dependent on the magnitude of the initial stress. During the recovery period, down-regulation of vitellogenin was observed at lowest exposure concentrations. The data presented here emphasize that links can be made between gene transcription changes and behavioral responses which is of great value for the evaluation and interpretation of biomarker responses.

Examination of the Interaction Between the Black Vine Weevil (Coleoptera: Curculionidae) and an Entomopathogenic Fungus Reveals a New Tritrophic Interaction

Abstract The purpose of this study was to characterize the behavior of black vine weevil larvae, Otiorhynchus sulcatus (F.), in the presence of two possible control options: the synthetic pyrethroid bifenthrin and the entomopathogenic fungus Metarhizium anisopliae (Metch.) Sorokin. Five third-instar black vine weevil were placed in two-choice soil olfactometers that allowed larvae to infest one of two pots. Larvae were allowed to choose between M. anisopliae (1 × 106 spores/g dry media) and untreated media, bifenthrin (25 ppm) and untreated media, as well as M. anisopliae– and bifenthrin-treated media. For all comparisons, experiments were conducted without plants in the system to test for innate responses, as well as with plants to test host–plant influence. Larvae were significantly deterred by bifenthrin without plants present in the system. No significant effect on larval preference was observed when M. anisopliae was present in media for trials without plants. M. anisopliae–treated media was preferre...

Host plant-induced changes in detoxification enzymes and susceptibility to pesticides in the twospotted spider mite (Acari: Tetranychidae).

Adult female twospotted spider mites, Tetranychus urticae Koch, reared on lima bean plants were moved to cucumber, maize, or new lima bean plants (the latter being a control) and evaluated after 24 h or 7 d for changes in susceptibility to three pesticides and in levels of related detoxification enzymes. The largest and most consistent changes were observed in mites feeding on cucumber. Susceptibility of mites on cucumber to the synthetic pyrethroids bifenthrin and lambda-cyhalothrin was greater than that of mites reared on lima bean and maize after only 24 h on the plants, and remained higher after 7 d. Mites on cucumber also were more susceptible to the organophosphate dimethoate than were mites on lima bean, but only after 7 d on the host. Susceptibility was inversely related to activities of both general esterase and glutathione S-transferase (GST) in mites on cucumber; general esterase and GST activities were 60 and 25% lower, respectively, than activities of twospotted spider mite on lima bean after 7 d of feeding. Mites on maize were slightly but significantly more susceptible than those on lima bean to bifenthrin, but not to lambda-cyhalothrin, after 7 d and to dimethoate after 24 h but not after 7 d. General esterase and GST activities in twospotted spider mite fed on maize for 24 h were 20 and 16% higher, respectively, than activities in twospotted spider mite on lima bean, but general esterase activity was 30% lower than lima bean-fed mites and GST was not different after 7 d. Thus, plant-induced changes in general esterase activity, perhaps in combination with GST activity, in twospotted spider mite appear to be inversely related to, and possibly responsible for, changes in susceptibility of twospotted spider mite to several pesticides, particularly the synthetic pyrethroids. General esterases appear to play less of a role in the detoxification of the organophosphate insecticide dimethoate.

Determination of endosulfan and some pyrethroids in waters by micro liquid-liquid extraction and GC-MS

A simple, rapid and reproducible method for the determination of some pesticide residues in water was developed using micro liquid-liquid extraction and gas chromatography - mass spectrometry with selected ion monitoring (GC/MS-SIM). The chlorinated insecticides α- and β-endosulfan and endosulfan-sulfate as well as the synthetic pyrethroids bifenthrin, permethrin, cypermethrin, fenvalerate and deltamethrin can be separated from a 500 mL sample water extracted with 0.5 mL of n-hexane containing anthracene-d10 as internal standard without clean-up in only 13 min. The recovery efficiencies of the tested compounds yielded more than 93.0% at a fortification level of 5 ng mL–1 and their relative standard deviations were between 1.9 and 11.7%. Detection limit of each compound ranged between 3 and 35 pg mL–1. The method was applied to ground, sea and tap waters from Almeria (Spain). The solubilities in water at 20° C were determined.