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PubMed2005

Separation and aquatic toxicity of enantiomers of synthetic pyrethroid insecticides.

Synthetic pyrethroid insecticides are chiral compounds with multiple asymmetric positions. In this study, isomers of four commonly used pyrethroids were separated at the enantiomeric level by enantioselective high-performance liquid chromatography (HPLC), and differences between enantiomers in aquatic toxicity were characterized using individual isomers. Isomers of cis-bifenthrin and permethrin were completely resolved on a Sumichiral OA-2500-I column. All eight isomers of cypermethrin and cyfluthrin were completely separated on two chained Chirex 00G-3019-DO columns. Great differences were found between enantiomers in the acute toxicity to aquatic invertebrates Ceriodaphnia dubia or Daphnia magna. In cis-bifenthrin (cis-BF) and cis-permethrin (cis-PM), the 1R-cis isomer was 15-38 times more active than the 1S-cis enantiomer, while in trans-PM, the 1R-trans isomer was substantially more toxic than the 1S-trans enantiomer. In cypermethrin or cyfluthrin, two of the eight isomers, 1R-cis-alphaS and 1R-trans-alphaS, contributed for almost all the toxicity in the racemate, while the other six enantiomers were inactive. These results suggest that significant enantioselectivity occurs for pyrethroids in aquatic toxicity, and such enantiomeric differences must be considered when evaluating ecological effects of pyrethroid insecticides.

Animals↗
PubMed2006

Rapid separation and determination of carbamate insecticides using isocratic elution pressurized capillary electrochromatography.

An isocratic elution pressurized CEC (pCEC) system was used to separate and determine ten carbamate insecticides. It was found that introduction of the electrical field, supplementary pressure, and SDS in the proposed method greatly improved the speed, column efficiency, selectivity, and repeatability for separation and determination of carbamates. On a capillary column of 75 microm ID packed with 3 microm octadecyl silica, baseline separation and detection of ten analytes was performed by using a mobile phase consisting of 30% v/v ACN and 70% v/v of 5 mmol/L ammonium acetate (pH 6.5) containing 1 mmol/L SDS and 0.01% triethylamine (TEA). Under the optimum conditions ten carbamate insecticides could be completely separated within 20 min. For the real vegetable samples, an SPE procedure for the cleanup of matrices was carried out prior to pCEC analysis. The detection limits of 0.05-1.6 mg/kg for ten carbamates and mean recoveries of 51.3-109.2% for eight kinds of vegetable samples at different concentrations of carbamates with RSD less than 11.4% were obtained, respectively. The proposed method has been proved to be effective in the rapid analysis of carbamate residues in vegetables.

Buffers↗
PubMedDate not supplied

Possible androgenic/anti-androgenic activity of the insecticide fenitrothion.

To date, within the field of endocrine disruption, much focus has been placed on chemicals that mimic oestrogens (so-called xenoestrogens), and the number of such chemicals apparently detected continues to grow steadily. Less effort has been expended on investigating chemicals that mimic, or antagonize, other hormones. Nevertheless, a number of chemicals have been reported to have a weak affinity for the androgen receptor, all of which have, to date, been found to have anti-androgenic activity in vivo. In this report, we present evidence that the insecticide fenitrothion can interact with the androgen, but not with the oestrogen, receptor. Using recombinant yeast expressing the human androgen receptor, we found that fenitrothion behaved as an androgen agonist in vitro when tested alone, and that it could antagonize the androgen DHT when both chemicals competed for the androgen receptor in vitro. In vivo studies using both intact and castrated male rats showed no conclusive androgenic or anti-androgenic responses. Changes in organ weights suggestive of anti-androgenic effects were mitigated against by the reduced body weights of fenitrothion-treated rats. The toxicity of the compound precluded the use of higher dose levels to substantiate any tentative findings. Interestingly, fenitrothion (and related insecticides) is structurally similar to flutamide, an anti-androgen used clinically that gives clearly positive responses in both intact and castrated rats.

Androgens↗
PubMedDate not supplied

Alterations in hepatic detoxifying enzymes induced by new organophosphorus insecticides following subchronic exposure in rats.

The present study examined the structure-toxicity relationship of two novel phosphorothionates, a methyl ester (RPR-II) and an ethyl ester (RPR-V), with regard to their interaction with certain biochemical indices in rat. Male rats were treated orally with 10% (low), 20% (medium) and 30% (high) doses of the two compounds (14, 28 and 42 microg kg(-1) day (-1) of RPR-II and 33, 66 and 99 microg kg(-1) day(-1) of RPR-V) daily for 90 days. The activity of hepatic glutathione S-transferase (GST) and UDP-glucuronyl transferase (UDPGT) and the level of glutathione (GSH) were estimated at 0, 45 and 90 days of treatment as well as 28 days after cessation of treatment. RPR-II caused statistically significant depletion of GSH after 45 and 90 days of treatment at the high dose, whereas RPR-V depleted GSH only after 90 days at the high dose. RPR-II inhibited GST after 45 and 90 days at medium and high doses, whereas RPR-V caused inhibition of GST after 45 and 90 days only at the high dose. Significantly, UDPGT activity was increased only by the high dose of RPR-II after 90 days. However, a dose and time-dependent increase in UDPGT activity was observed at all three doses of RPR-V after 45 and 90 days. There was no modulation in any of the three indices at low doses of the two organophosphorus insecticides. The withdrawal study revealed that induced changes in hepatic parameters were reversible 28 days after cessation of treatment. The results indicated that the two insecticides had different potential to modulate hepatic GST, UDPGT and GSH due to subchronic exposure and that these metabolic alterations are quite reversible after withdrawal of treatment.

Administration, Oral↗
PubMed1985

Notochordal development as influenced by the insecticide dicrotophos (Bidrin).

White Leghorn chicken embryos were treated at different ages with the insecticide dicrotophos to determine the time period of maximum effect upon notochordal development. Doses of insecticide ranging from 250 micrograms to 2.0 mg were injected into eggs at 8, 16, 24, 32, 40, 48, 72, or 96 hr of incubation and the eggs allowed to incubate for an additional 48 hr. Dicrotophos treatment caused dorsoventral and lateral folding of the notochord, with the cervical region being most severely affected. Although there was no apparent difference in dose responsiveness at any one age, there was an obvious age relationship. Notochordal responsiveness, expressed as both the number and severity of folds, was low among the 8- and 16-hr treated embryos, increased to a maximum in the 48-hr treatment group, and then declined among the older embryos. The time of maximum effect correlates closely with the time of sheath deposition and vacuolization of the notochord, but not to initial formation of the notochord from the mesoblast or later extracellular matrix production by sclerotome cells. It is proposed that dicrotophos interferes with some aspect of sheath formation. The pressure exerted by the vacuolization upon a structurally weakened sheath is thought to cause the observed folding.

Abnormalities, Drug-Induced↗
PubMed1989

Effects of the organophosphate insecticides diazinon and parathion on bobwhite quail embryos: skeletal defects and acetylcholinesterase activity.

Bobwhite quail eggs were injected at 48 or 72 hr of incubation with various doses of the organophosphate (OP) insecticides diazinon or parathion and the embryos were examined after an additional 48 hr of incubation by both histological and cartilage-staining methods. Bobwhite embryos did not display the notochordal folding or vascular enlargement reported for OP-injected chicken embryos. Cartilage staining of embryos injected with insecticide at 72 hr of incubation and recovered at day 12 of incubation revealed severe shortening and contortion of the vertebral axis, as well as tibiotarsal, rib, and sternum defects. Parathion was more potent in causing skeletal defects than diazinon. No type I defects (micromelia, parrot beak) were detected. Radiometric acetylcholinesterase (AChE) assays of whole embryo homogenates were performed for day 6, 9, and 12 diazinon-injected and control embryos. Diazinon effected drastic reductions in AChE activity. Although the AChE and axial skeletal responses of bobwhite embryos to OP injection are similar to those reported in the literature for other species, some major differences in the bobwhite response were noted: namely, the absence of notochordal folding in the young bobwhite embryo and the absence of type I defects at day 12. These differences suggest that further studies with the bobwhite quail would be useful in clarifying the mechanisms involved in OP-induced teratogenesis.

Acetylcholinesterase↗
PubMed2004

Differences in retention of dioxin-like compounds and organochlorinated insecticides on an immunochromatographic column. Interpretation and applicability.

The retention of organochlorinated compounds on an immunochromatographic column is studied. The compounds considered are usually found together in real samples of environmental concern, and include chlorinated biphenyls, chlorinated dibenzo-p-dioxins, chlorinated dibenzofurans, and organochlorinated insecticides. The different retention observed for different compounds is interpreted in light of the structural similarities of the compound studied with that used as a hapten to raise the antibodies employed as ligands in the immunochromatographic column. Differences in retention of the organochlorinated compounds on the immunocolumn make it possible to fractionate them. Mixtures of phosphate buffer solution and ACN in different ratios were used as desorption agents. Depending on the percentage of ACN employed, different fractionations of the organochlorinated compounds are obtained. The use of 20% ACN allows fractionation of most insecticides from chlorinated biphenyls, dioxins, and furans. Besides, chlorinated biphenyls of different chlorination degree can be separated. Moreover, pentachlorinated dioxins and pentachlorinated furans are separated from hexachlorinated biphenyls. Fractionation is of critical importance from a practical point of view, as it avoids some of the interferences that otherwise take place during the subsequent gas chromatography/mass spectrometry (GC/MS) analysis of these compounds. In this way, immunochromatography makes it possible to perform in a single step all the processes (extraction, clean-up, concentration, and fractionation) that are needed prior to the GC/MS analysis of these analytes in aqueous samples. An additional advantage of this method is the reusability of the immunoaffinity chromatography column for more than 500 times.

Chromatography↗
PubMed1992

Purification and crystallization of insecticidal delta-endotoxin CryIIIB2 from Bacillus thuringiensis.

CryIIIB2, an insecticidal protein from Bacillus thuringiensis has been crystallized from 0.6 M NaBr and HEPES buffer at pH 7.0 and X-ray diffraction data collected on a native crystal to 2.4 A. The insecticidal protein was obtained from a Bacillus thuringiensis (Bt) strain EG7231. Crystals of the endotoxin are orthorhombic, space group C2221, with unit cell dimensions of a = 122.44, b = 131.81, and c = 105.37 A. A unit cell contains one molecule of the 67,000 Da endotoxin per asymmetric unit.

Bacillus thuringiensis↗
PubMed2006

Effect of pretreatment with piperonyl butoxide on pyrethroid efficacy against insecticide-resistant Helicoverpa armigera (Lepidoptera: Noctuidae) and Bemisia tabaci (Sternorrhyncha: Aleyrodidae).

Pyrethroid resistance in B-type Bemisia tabaci Gennadius and Australian Helicoverpa armigera Hübner field populations is primarily conferred by esterase isoenzymes which metabolise and sequester pyrethroid insecticides. It has been shown previously that pyrethroid resistance-associated esterases in H. armigera are inhibited by the insecticide synergist piperonyl butoxide (PBO) over a 22-h period. It is demonstrated here that similar inhibition can be obtained against B-type B. tabaci. Small-scale field trials showed excellent levels of pyrethroid control when insects were pretreated with PBO and then dosed with pyrethroid during the time of maximum esterase inhibition. These results demonstrate that PBO can restore pyrethroid efficacy in the field against both B-type B. tabaci and resistant H. armigera.

Animals↗
PubMed2006

Use of oils combined with low doses of insecticide for the control of Myzus persicae and PVY epidemics.

Experiments were carried out in the laboratory to assess the insecticidal effect on Myzus persicae Sulzer of different oils applied alone or combined with imidacloprid or pirimicarb. The oils tested were a horticultural mineral oil, a refined rapeseed oil, a refined soya oil and a raw fish oil. When the oils were sprayed alone on pepper plants infested with M. persicae, mineral oil caused the highest mortality of aphids (over 80%). Applied before aphid infestation of pepper leaves and in mixture with low doses of imidacloprid (at one-fifth of the dose recommended by the manufacturer) and pirimicarb (at one-tenth of the dose recommended by the manufacturer), the oils did not significantly increase the toxicity of the insecticides alone. However, sprayed on aphid-infested pepper plants, the mortality rates achieved by imidacloprid/mineral oil and imidacloprid/rapeseed oil mixtures were significantly higher than those achieved by imidacloprid alone at 16 and 24 h. In a field experiment the effect on the incidence of the potato virus (PVY) of the oils in combination with imidacloprid was determined. Mineral oil, rapeseed oil and soya oil were sprayed eight times onto seed potato plants treated with imidacloprid before sowing. Mineral oil reduced PVY-infected plants by 60% and rapeseed oil by 40% compared with plots treated with imidacloprid. The oils applied as 10 ml litre-1 emulsions in water did not cause symptoms of phytotoxicity on the potato plants, and yield was not reduced.

Animals↗
PubMed2007

Disruption of mating in codling moth (Lepidoptera: Tortricidae) by chlorantranilipole, an anthranilic diamide insecticide.

The influence of the anthranilic diamide insecticide chlorantranilipole (DPX-E2Y45; Rynaxypyr against the adult stage of codling moth, Cydia pomonella L., was examined. Insecticide residues in plastic cups sprayed with 56 mg AI L(-1) (equivalent to the recommended field rate) had a minimal effect on adult survival or fecundity, but significantly fewer female moths were mated in treated than in untreated cups. Similar results were found in field studies with adults placed in screened cages on treated apple foliage for up to 3 weeks. Mating was disrupted when either sex was topically dosed with technical material (0.01-0.1 microg). Males were more sensitive to the disruptive effects of chlorantranilipole than females. A 2 h exposure significantly reduced male activity (walking and wing fanning), but not female calling. A 25 h exposure significantly reduced the activity of both sexes. The proportion of males landing near a sex pheromone source in a flight tunnel was significantly reduced following exposures of 2-4 h and completely eliminated following a 17 h exposure. Male moths partially recovered from either topical or residual exposure to chlorantranilipole, but the extent of their recovery was dose and time dependent. Male response to sex pheromone recovered within 2 h following a 4 h exposure, but following a 17 h exposure only a partial recovery occurred after 48 h. Mating by moth pairs exposed to chlorantranilipole residues for 24 h did not significantly increase during recovery periods of 24-96 h, except in cups treated with 10% of the standard concentration. The proportion of field-collected female codling moths caught in pear ester-baited traps that were mated was significantly lower in apple orchards treated season-long with chlorantranilipole compared with females caught in either untreated orchards or those treated with sex pheromones to cause mating disruption.

Animals↗
PubMed2001

Enhanced efficiency of electrostatically charged insecticide aerosols.

The bioefficacy of a standard domestic aerosol insecticide has been compared with that of a similar spray in which the droplets were electrostatically charged. The aerosol was charged without the need for an external power supply, by enhancing natural charge separation processes that occur during atomisation. The charge-to-mass ratio achieved was 1.1 x 10(-4) C kg-1, compared with 2.2 x 10(-5) C kg-1 for the standard aerosol. Efficiency was assessed for insects in free flight. A direct space-spray application method was used to study the bioefficacy of these aerosols on houseflies, Musca domestica, and an indirect space-spray method on houseflies and mosquitoes, Culex quinquefasciatus. Two levels of concentration of active ingredients were compared. At low concentrations of 1.57 g kg-1 of bioallethrin and 0.29 g kg-1 of bioresmethrin, the charged aerosol achieved a significant reduction in KDT50 (time at which 50% of the flies were knocked down), compared with the standard aerosol. In the direct spray application to houseflies, the KDT50 was reduced by 50%, while in the indirect spray the KDT50 was reduced by 40%. In the indirect spray of mosquitoes, the KDT50 was reduced by 22%. With higher active ingredient concentrations of 2.09 g kg-1 for bioallethrin and 0.39 g kg-1 for bioresmethrin, the charged aerosol also demonstrated faster knockdown than the standard, but the improvement was less marked. In the direct spray application to houseflies, the KDT50 was reduced by 21% compared with the standard aerosol, while in the indirect spray the KDT50 was reduced by 16%. In the indirect spray of mosquitoes, the KDT50 was reduced by 24%. The percentage mortality after 24 h was also increased with the charged aerosol. Charge carried by the droplets results in increased interception of the insecticide, as the droplets are attracted to the insects in flight and space charge effects within the aerosol could cause improved dispersion in the test chamber.

Aerosols↗
PubMed2001

Natural products as insecticides: the biology, biochemistry and quantitative structure-activity relationships of spinosyns and spinosoids.

The spinosyns, a novel family of insecticidal macrocyclic lactones, are active on a wide variety of insect pests, especially lepidopterans and dipterans. The biological activity of a mixture (spinosad; Tracer, Spin-Tor, Success) of the two most abundant spinosyns (spinosyns A and D) against pest insects is on a par with that of many pyrethroid insecticides. The spinosyns also exhibit a very favorable environmental and toxicological profile, and possess a mode of action that appears unique, with studies to date suggesting that both nicotinic and gamma-aminobutryic acid receptor functions are altered in a novel manner. Compared to pyrethroids such as cypermethrin, spinosyn A is slow to penetrate into insect larvae such as tobacco budworm larvae (Heliothis virescens); however, once inside the insect, spinosyn A is not readily metabolized. To date, more than 20 spinosyns and more than 800 spinosoids (semi-synthetic analogs) have been isolated or synthesized, respectively. Artificial neural network-based quantitative structure activity relationship (QSAR) studies for the spinosyns suggested that modification of the 2',3',4'-tri-O-methylrhamnosyl moiety could improve activity and several spinosoids incorporating these modifications exhibited markedly improved lepidopteran activity compared to spinosad. Multiple linear regression-based QSAR studies also suggest that whole molecule properties such as CLogP and MOPAC dipole moment can explain much of the biological activity observed for the spinosyns and closely related spinosoids.

Animals↗
PubMed2001

Neonicotinoid insecticides alter diapause behavior and survival of overwintering white grubs (Coleoptera: Scarabaeidae).

The chloronicotinyl, imidacloprid, and the thianicotinyl, thiamethoxam, are effective insecticides against white grubs when applied as preventative treatments during or immediately after egg laying. Their efficacy sharply declines when the grubs reach late-instar stage. As both imidacloprid and thiamethoxam act on post-synaptic nicotinic acetylcholine receptors and modify insect behavior, we hypothesized that the two compounds will interfere with overwintering behavior of scarabs, thus reducing their ecological fitness and exposing them to increased winter mortality. We tested this hypothesis by applying the two compounds curatively against late second-instar and early third-instar Popillia japonica and Cyclocephala borealis grubs in turfgrass. Imidacloprid provided control of P japonica equivalent to the most widely used curative organophosphate, trichlorfon, by 14 days after treatment, but thiamethoxam had no affect. In contrast, both imidacloprid and thiamethoxam caused significant reductions in C borealis populations. Both insecticides altered the overwintering behavior of P japonica by significantly reducing the normal downward movement of grubs in October. Halofenozide, an ecdysone agonist, also caused rapid mortality of the late second-instar C borealis equivalent to trichlorfon, but had no affect on P japonica. In another experiment on a site naturally infested with entomopathogenic nematodes, the exclusive treatment of third-instar P japonica with imidacloprid resulted in no significant mortality in the autumn (up to 15 days after treatment), but caused a significant reduction in the survival of overwintered grubs. There was an increase in the numbers of grubs infected with nematodes in the imidacloprid and trichlorfon treatments compared with control, but these differences were significant only for trichlorfon. These results indicate that imidacloprid can effectively control late second-instars of both P japonca and C borealis and can significantly reduce survival of overwintered third-instar P japonica by altering their normal overwintering behavior.

Animals↗
PubMed2002

Nicotinic acetylcholine receptor binding of imidacloprid-related diaza compounds with various ring sizes and their insecticidal activity against Musca domestica.

Fifteen 5-substituted 1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-1,3- diazacyclohexanes and three other related compounds having a five- or seven-membered ring were synthesized and their biological activities were measured in vivo and in vitro. The insecticidal (in vivo) activity was evaluated against houseflies Musca domestica L under synergistic conditions with propargyl propyl phenyl phosphonate and piperonyl butoxide. The binding activity of each compound to nicotinic acetylcholine receptor in vitro was measured using [125I] alpha-bungarotoxin. The insecticidal activities of the unsubstituted diazacyclohexane analogues were slightly higher than those of the imidazolidine analogues, but the enlargement of ring size to diazacycloheptane lowered the activity. Substitution of 1,3-diazacyclohexane or imidazolidine rings was not generally favourable for the activity, but the unsubstituted 1,3-diazacyclohexane analogue showed the highest binding activity. Ring substitutions and ring enlargement decreased the activity 100-30,000-fold.

Animals↗
PubMed2002

Structural effects of dinotefuran and analogues in insecticidal and neural activities.

The insecticidal potencies of dinotefuran and analogues against the adult male American cockroach, Periplaneta americana (L) were measured by injection with or without metabolic inhibitors. The potency of dinotefuran was close to those of clothianidin and imidacloprid under the conditions used. The nerve-excitatory and nerve-blocking activities were measured with central nerve cords of P americana. The nerve-excitatory activity of dinotefuran was lower than that of imidacloprid, but was comparable with that of clothianidin. The nerve-blocking activity of dinotefuran was comparable with that of imidacloprid and slightly higher than that of clothianidin. Quantitative analyses showed that variations in the insecticidal activity were better correlated with variations in the nerve-blocking activity than with those in the nerve-excitatory activity when the contribution of the hydrophobic factor was allowed for.

Animals↗
PubMed2002

Activated transformations of organophosphorus insecticides in the case of non-AChE inhibitory oxons.

Many organophosphorus (OP) compounds are of the thiono form and in insects or animals are converted by microsomal mixed function oxidases (MFO) into the oxon forms which inhibit acetylcholinesterase (AChE) and give toxic activity. However, certain S-alkyl phosphorothiolates (RS-P(O) <) such as methamidophos, profenophos and prothiophos oxon are strongly insecticidal, but very poor inhibitors of AChE in vitro. Their oxons are converted further to the S-oxides, which either inhibit AChE or decompose, depending on the alkyl substituents on the sulfur atom. It is also inferred in the case of prothiophos oxon that its S-oxide not only inhibits AChE but also conjugates with glutathione (GSH) by the action of glutathione S-transferase (GST), and the conjugate inhibits AChE. Certain phosphoramidates (R2N-P(O) <) such as isofenphos oxon, schradan and propetamphos oxon are weak AChE inhibitors, but strongly insecticidal. It is well known that isofenphos oxon is converted into the stable N-desalkyl form (H2N-P(O) <) by oxidative dealkylation to inhibit AChE. The authors have studied activation of phosphoramidates using 2,4-dichlorophenyl methyl N-alkylphosphoramidates as model compounds using various approaches including computational chemistry, and these studies indicated that the O-aminophosphate structure (R2N-O-P(O) <) is an activated form.

Acetylcholinesterase↗
PubMed2003

Field relevance of a synergistic effect observed in the laboratory between an EBI fungicide and a chloronicotinyl insecticide in the honeybee (Apis mellifera L, Hymenoptera).

It had been found earlier that the chloronicotinyl insecticide thiacloprid (as the 480 g litre(-1) SC Calypso) poses a favourably low toxicity hazard to the honeybee, Apis mellifera L. As with pyrethroids, the metabolization of chloronicotinyl compounds involves monooxygenases, which are known to be inhibited by some ergosterol biosynthesis inhibitor (EBI) fungicides potentially co-applied with these insecticides. The potential synergistic enhancement of the toxicity of thiacloprid to honeybees when co-applied with such fungicides was therefore studied under laboratory and semi-field conditions. Fungicides of other chemical classes were also examined for synergistic potential to reveal other metabolic interactions. In the laboratory, only a slight synergistic effect was observed with the anilinopyrimidine fungicide examined, while a significant enhancement of thiacloprid toxicity to honeybees was found with EBI fungicides. In three tunnel tests conducted under different environmental conditions to simulate field exposure, no increased mortality was observed when honeybees were directly sprayed with thiacloprid (Calypso) alone or in combination with the EBI fungicide tebuconazole (250 g litre(-1) EW, Folicur). There was also no synergized reduction in the foraging intensity on the treated crop. In general, the foraging intensity decreased after thiacloprid treatment but was restored within 24-48 h. The hive vitality was not affected by either thiacloprid or its tank mix with tebuconazole. Our results suggest that, at the recommended use rates, thiacloprid poses a negligible lethal risk to honeybees when applied either alone or in tank mixes with fungicides of various chemical classes.

Animals↗