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At least 19 recordsLinked to original sources

PubMed1996

Monooxygenase, Esterase, and Glutathione Transferase Activity Associated with Azinphosmethyl Resistance in the Tufted Apple Bud Moth, Platynota idaeusalis

Azinphosmethyl-selected tufted apple bud moths were compared to susceptible and reverted strains with respect to possible metabolic mechanisms of resistance within the third instar, fifth instar, and adults. Based upon bioassays conducted by topical application with azinphosmethyl, LD50s were as high as 867-fold in the selected strain as compared to that seen in susceptible bud moths. The LD50 of the reverted strain was intermediate to that of the susceptible and selected insects at all stages studied. Glutathione transferase activity measured with 1-chloro-2,4-dinitrobenzene was elevated in the selected strain 1.6- and 2.2-fold as compared to third and fifth stadium susceptible bud moths, respectively. No consistent strain differences were noted for 1,2-dichloro-4-nitrobenzene. Cytochrome P450 content and P450 mRNA was not significantly different in fifth instars of the susceptible and selected strain. However, there was a 2.7- and 1.9-fold increase in benzphetamine and p-nitroanisole metabolism, respectively, in the guts of azinphosmethyl-selected fifth instars. Benzo[a]pyrene metabolism was elevated 2.4-fold in the carcass of selected bud moths and no differences were noted for methoxyresorufrin in either gut or carcass. Susceptible fifth instars demonstrated a reduced rate of metabolism of azinphosmethyl to the oxon and methyl benzazamide. Piperonyl butoxide failed to synergize azinphosmethyl toxicity. Esterase activity measured with 1-naphthyl acetate and p-nitrophenyl acetate was elevated in selected larvae compared to that seen in susceptible tufted apple bud moths in both larvae and adults. This increased esterase activity was attributed to several isoforms as resolved by analytical isoelectric focusing. One of these forms was consistently overexpressed in all of the life stages examined. Pretreatment of selected fifth instars with S,S,S-tributylphosphorotrithioate increased the toxicity of azinphosmethyl 400-fold and had minimal effect on toxicity in susceptible insects. It appears that multiple hydrolases are the primary metabolic factor in azinphosmethyl resistance in the tufted apple bud moth.

Journal Article↗

PubMed2001

Susceptibility of male oriental fruit moth (Lepidoptera: Tortricidae) populations from New Jersey apple orchards to azinphosmethyl.

Toxicological responses to azinphosmethyl of male Oriental fruit moth, Grapholita molesta (Busck), from five commercial orchards in which control failures had occurred were examined for azinphosmethyl resistance and for potential resistance mechanisms by using topical pheromone trap bioassay and compared with a reference population that had no history of control failure and had received little selection pressure. The 1998 field survey indicated moderate level of resistance to azinphosmethyl (2.7-4.1-fold); slopes of regressions lines (2.47-2.76) indicate genetically heterogeneous populations. An approximate twofold decline was observed between the fourth flight of 1998 and the first flight of 1999, suggesting the presence of unstable resistance in moths collected from these study sites. The 1999 field surveys indicated lower levels of tolerance to azinphosmethyl. The resistance ratios ranged from 1.17 to 1.86 during the first flight of 1999 and 1.24-2.64 during the fourth flight of 1999. Steep slopes of the concentration-response lines during 1999 season indicated the presence of genetically homogeneous populations with some exceptions. A 1.5-2.0-fold increase was observed between the first and fourth flights of 1999, indicating that resistance can build up during the growing season. S,S,S,-tri-n-butyl phosphorotrithioate (DEF), but not piperonyl butoxide, significantly enhanced the toxicity of azinphosmethyl, suggesting that enhanced metabolism by esterases is involved in the tolerance of azinphosmethyl in moths collected from these study sties.

Animals↗

PubMed1978

Bioassay of azinphosmethyl for possible carcinogenicity.

A bioassay of technical-grade azinphosmethyl for possible carcinogenicity was conducted by administering the test chemical in feed to Osborne-Mendel rats and B6C3F1 mice. Groups of 50 rats of each sex were administered azinphosmethyl at one of two doses for 80 weeks, then observed for 34 or 35 weeks. Time-weighted average doses of either 78 or 156 ppm were used for the males. Initial doses of 62.5 or 125 ppm used for the females were maintained throughout the bioassay. Matched controls consisted of groups of 10 untreated rats of each sex; pooled controls consisted of the matched controls combined with 95 male and 95 female untreated rats from similar bioassays of 10 other test chemicals. All surviving rats were killed at 114 or 115 weeks. Groups of 50 mice of each sex were administered azinphosmethyl at one of two doses for 80 weeks, then observed for 12 or 13 weeks. The doses were either 31.3 or 62.5 ppm for the males and either 62.5 or 125 ppm for the females. Matched controls consisted of groups of 10 untreated mice of each sex; pooled controls consisted of the matched controls combined with 130 male and 120 female untreated mice from similar bioassays of 11 other test chemicals. All surviving mice were killed at 92 or 93 weeks. High- and low-dose male rats and mice and high-dose female rats and mice had lower mean body weights than corresponding matched controls throughout the bioassay. Typical signs of organophosphate intoxication were observed in a few animals of both species, and included hyperactivity, tremors, and dyspnea. Sufficient numbers of animals were at risk in each species for development of late-appearing tumors. A great many tumors of the endocrine organs were observed in both dosed male and dosed female rats. Those of the adrenal in dosed males and females, the follicular cells of the thyroid in dosed females, the anterior pituitary in dosed males, and the parathyroid in dosed males occurred at statistically significant incidences when compared with pooled controls, but not with matched controls, and they were not considered to be related to administration of the test compound. The incidences of tumors of the pancreatic islets and of the follicular cells of the thyroid in the male rats suggest, but do not clearly implicate, azinphosmethyl as a carcinogen in these animals. In mice of each sex there were no increased incidences of tumors that could be related to administration of the test chemical. It is concluded that under the conditions of this bioassay, neoplasms of the thyroid and pancreatic islets suggest but do not provide sufficient evidence for the carcinogenicity of azinphosmethyl in male Osborne-Mendel rats. Azinphosmethyl was not shown to be carcinogenic in female Osborne-Mendel rats or in B6C3F1 mice of either sex.

Journal Article↗

PubMed2004

Adsorption kinetics of azinphosmethyl from aqueous solution onto pyrolyzed Horseshoe sea crab shell from the Atlantic Ocean.

The adsorption behavior of azinphosmethyl on pyrolyzed Horseshoe Crab (Limulus polyphemus) outer shell, as a residue, from the Atlantic Ocean, collected along the Maine coast, USA, has been studied with regards to its kinetic and equilibrium conditions, taking into account adsorbate concentrations of 2 x 10(-3), 4 x 10(-3), 6 x 10(-3), and 8 x 10(-3), as well as temperatures of 30 degrees C, 40 degrees C, 50 degrees C, and 60 degrees C. The yield of adsorption of azinphosmethyl from aqueous solution ranged from 56.1% to 61% with temperature increasing. Kinetic studies showed that adsorption rate decreased as the initial azinphosmethyl concentration increased. It was found, that the adsorption reaction obeyed first-order kinetics. The overall rate constants were estimated for different temperatures. The activation energy for adsorption was about 1.52 kJmol(-1), which implies that azinphosmethyl mainly adsorbed physically onto Horseshoe Crab outer shell. Langmuir and Freundlich isotherms were applied to the experimental data and isotherm constants were calculated. The thermodynamic parameters DeltaG0, DeltaH0 and DeltaS0 for the adsorption reaction were evaluated based on equilibrium data and in connection with this result the thermodynamic aspects of adsorption reaction were discussed. The adsorption was found to be endothermic in nature. The adsorbent used in this study proved highly efficient for the removal of azinphosmethyl.

Adsorption↗

PubMed2000

Correlated insecticide cross-resistance in azinphosmethyl resistant codling moth (Lepidoptera: Tortricidae).

Resistance to several classes of insecticides was correlated with azinphosmethyl resistance in codling moth, Cydia pomonella (L.), in California. In tests of laboratory and field populations, cross-resistance was positively correlated with azinphosmethyl and two organophosphates (diazinon, phosmet), a carbamate (carbaryl), a chlorinated hydrocarbon (DDT), and two pyrethroids (esfenvalerate and fenpropathrin). Additionally, negatively correlated cross-resistance was identified between azinphosmethyl and two other organophosphates, chlorpyrifos and methyl parathion. Patterns of resistance observed in laboratory colonies were confirmed with field bioassays. In bioassays of field populations, azinphosmethyl resistance was observed to increase from 1991 to 1993, although levels of resistance remained < 13-fold. Because orchards with azinphosmethyl resistance have had difficulties with suppression of codling moth, and cross-resistance was found for all tested classes of insecticides, strategies for managing resistance will need to be developed so as to protect current and future control tactics. The two insecticides with negatively correlated cross-resistance are discussed as potential tools for resistance management.

Animals↗

PubMed1978

Personnel safety and foliage residue in an orchard spray program using azinphosmethyl and captan.

Residue levels of azinphosmethyl and captan were determined from blotter paper patches attached to the clothing of personnel participating in an orchard spray program. Average exposure of 1.74 mg/man/hr for azinphosmethyl and 1.94 mg/man/hr for captan were extrapolated from mean residue values obtained from analyzing the patches. Azinphosmethyl residue found on apple and peach foliage had been reached by 69% by the tenth day post-application, while captan residue had been reduced 50% for the same period. There was no evidence of a buildup of either azinphosmethyl or captan on treated foliage as the season progressed.

Agricultural Workers' Diseases↗

PubMed2000

Combined effects of 2,4-D and azinphosmethyl on antioxidant enzymes and lipid peroxidation in liver of Oreochromis niloticus.

This study aims to investigate the effects of the herbicide 2,4-D and the insecticide azinphosmethyl on hepatic antioxidant enzyme activities and lipid peroxidation in tilapia. Fish were exposed to 27 ppm 2,4-D, 0.03 ppm azinphosmethyl and to a mixture of both for 24, 48, 72 and 96 h. Activities of catalase (EC 1.11.1.6), glutathione-S-transferase (GST, EC 2.5.1.18) and the level of malondialdehyde (MDA) in the liver of Oreochromis niloticus exposed to 2,4-D and azinphosmethyl, both individually and in combination, were not affected by the pesticide exposures. However, glucose-6-phosphate dehydrogenase (G6PD, EC 1.1.1.49) and glutathione reductase (GR, EC 1.6.4.2) activities in individual and combined treatments, increased significantly compared to controls. Furthermore, glutathione peroxidase (GPx, EC 1.11.1.9) activity increased in individual treatment, while the same enzyme activity decreased in combination. 2,4-D did not affect the activity of superoxide dismutase (SOD, EC 1.15.1.1), but the activity of this enzyme in azinphosmethyl treatment decreased, while its activity increased in combination. Combined treatment of the pesticides exerted synergistic effects in the activity of SOD, while antagonistic effects were found in the activities of G6PD, GPx, GR. The results indicate that O. niloticus resisted oxidative stress by antioxidant mechanisms and prevented increases in lipid peroxidation.

2,4-Dichlorophenoxyacetic Acid↗

PubMed2003

The effect of the 14-day agricultural restricted entry interval on azinphosmethyl exposures in a group of apple thinners in Washington state.

We examined the effect of the 14-day agricultural restricted entry period on absorbed pesticide doses in a group of twenty experienced apple thinners. Thinners entered orchards 1-49 days following azinphosmethyl applications. Urine samples (n=296) collected throughout the thinning season were analyzed for the three dialkylphosphate metabolites of azinphosmethyl to estimate absorbed daily doses. Separate dose distributions were created for samples collected when the interval was <14 days, or 14 days or more; geometric mean doses for these two categories differed by a factor of two (42 and 19 microg/kg/day, respectively; p<0.0001). Dose estimates were compared to US Environmental Protection Agency and California EPA regulatory guidance values for occupational azinphosmethyl risk. None of the doses exceeded the U.S. EPA NOAEL (560 microg/kg/day), but nearly all had a margin of exposure of less than 100. Addition of a 10-fold uncertainty factor to California EPAs NOAEL produced a guidance value of 75 microg/kg/day. Only 2.4% of the doses exceeded this value for re-entry intervals 14 days or more, while 27% exceeded the value for re-entry intervals <14 days. We conclude that the 14-day restricted entry interval provides an appropriate level of worker health protection under the field conditions studied.

Agriculture↗

PubMed1996

A Point Mutation of Acetylcholinesterase Associated with Azinphosmethyl Resistance and Reduced Fitness in Colorado Potato Beetle

A serine to glycine point mutation of acetylcholinesterase (AChE, EC 1.1.1.7) was identified in an azinphosmethyl-resistant strain of Colorado potato beetle [Leptinotarsa decemlineata (Say)]. The position of the mutation corresponds to Val 238 of the Torpedo AChE and represents the first amino acid residue to form the alpha-helix, alpha-E'1. The predicted secondary structure of the mutation-containing region of AChE suggested that the transition from the turn to the alpha-helix occurs sooner in the sequence when serine is replaced by glycine. Thus, conformational changes in the AChE due to the alpha-helix deformation were expected to impinge upon both the catalytic and the peripheral binding sites, resulting in the modification of the bindings of organophosphorus insecticides and other ligands to these sites. The mutation appeared to be associated with the fitness of the beetle. The intrinsic rate of increase of the azinphosmethyl-resistant (AZ-R) strain was relatively low when the beetles were reared on the Russet Burbank potato cultivar, but was relatively high when they were reared on the NDA 1725-1 potato cultivar. Because these two potato cultivars contain different amounts of steroidal glycoalkaloids (e.g., alpha-solanine and alpha-chaconine), the different fitness of the AZ-R strain on different potato cultivars may be partially attributed to the increased sensitivity of the azinphosmethyl-resistant form of AChE to the inhibition by alpha-solanine and reduced sensitivity to alpha-chaconine as previously reported.

Journal Article↗

PubMed2002

Marker enzyme assessment in the liver of cyprinus carpio (L.) exposed to 2,4-D and azinphosmethyl.

The potential utility of antioxidant enzymes and lipid peroxidation as indicators of exposure to 2,4-D and azinphosmethyl together with the toxic effects of these compounds in freshwater fish Cyprinus carpio were evaluated. Biochemical parameters were recorded spectrophotometrically in fish liver, which were exposed to a single dose of 2,4-D and azinphosmehtyl (1/3 LC(50)), and their mixture at 1:1 ratio for 24, 48, 72, and 96 h. The most sensitive parameter was glutathione S-transferase (GST) activity, which significantly increased with experimental exposures. Glucose 6-phosphate dehydrogenase activity did not change after 24 and 48 h while there was an elevation after 72 h in all exposure groups. The activity decreased only when these were applied in combination at 96 h. Superoxide dismutase activity increased after azinphosmethyl exposure for 48 and 96 h. 2,4-D decreased the activity after 24 h while the activity remained at the same level with control after 48 h. An elevation was found between 72 and 96 h. Mixture treatment did not changed the activity. Glutathione reductase and catalase enzyme activities, and malondialdehyde levels remained constant in all the treatment groups compared with controls. These results suggest that induction of GST activity may be used as biomarker for the assessment of water pollution in C. carpio.

2,4-Dichlorophenoxyacetic Acid↗

PubMed2004

Tissue-specific oxidative stress responses in fish exposed to 2,4-D and azinphosmethyl.

Species- and tissue-specific defenses against the possibility of oxidative stress and lipid peroxidation were compared in adult fish, Oreochromis niloticus and Cyprinus carpio, exposed to 2,4-dichlorophenoxyacetic acid (2,4-D), azinphosmethyl and their combination for 96 h. Superoxide dismutase (SOD), glutathione peroxidase (GPx) and catalase activities were monitored in kidney, brain and gill. In all exposure groups there was a marked increase in SOD activity in gill tissues in both fish species, while it was at the control level in other tissues. The highest elevation of SOD activity by combined treatment was observed in C. carpio. Individual and combined treatments caused an elevation in catalase and GPx activities in kidney of C. carpio. Catalase activity was unaffected in brain of O. niloticus, while GPx activity was decreased after all treatments. Glutathione S-transferase (GST) activity was higher than the control levels in kidney of both fish exposed to pesticides. No significant changes were observed in malondialdehyde level in kidney and brain of C. carpio. Our results indicate that the toxicities of azinphosmethyl and 2,4-D may be related to oxidative stress. Also, the results show that SOD activity in gill and GST activity in kidney may be used as biomarkers for pollution monitoring and indicate that the activities of certain biomarkers in C. carpio are more sensitive to pesticides than those in O. niloticus.

2,4-Dichlorophenoxyacetic Acid↗

PubMed2006

Kinetics and thermodynamics of adsorption of azinphosmethyl from aqueous solution onto pyrolyzed (at 600 degrees C) ocean peat moss (Sphagnum sp.).

The removal of azinphosmethyl from aqueous solution onto pyrolyzed ocean peat moss (Sphagnum sp.), as a residue, from the Rhode Island coast (USA), has been investigated at different temperatures and initial concentrations. The ocean peat moss had been pyrolyzed at 600 degrees C in nitrogen atmosphere before the adsorption process. The kinetic data obtained from batch studies have been analyzed using pseudo-first order kinetic model. The rate constants were evaluated at different temperatures. The thermodynamic parameters (DeltaG degrees , DeltaH degrees , DeltaS degrees ) for the adsorption process were calculated and the results suggest that the nature of adsorption is endothermic and the process is spontaneous and favorable. The activation energy for adsorption process was estimated, about 18.3 kJ mol(-1). According to this value the adsorption of azinphosmethyl onto pyrolyzed ocean peat moss is in the range of physical adsorption. The experimental data have been modeled using Langmuir, Freundlich and Temkin isotherms. It was found that Langmuir and Freundlich isotherms give the best correlation with the experimental data.

Adsorption↗

PubMed2004

Time course of brain cholinesterase inhibition and recovery following acute and subacute azinphosmethyl, parathion and carbaryl exposure in the goldfish (Carassius auratus).

Laboratory toxicity data contrasting mortality and brain cholinesterase inhibition in the goldfish (Carassius auratus) are presented. Brain cholinesterase (ChE) was greatly reduced after 96 h of exposure in vivo at sublethal concentrations of azinphosmethyl and parathion. The inhibition of the enzyme was dose dependent, and concentrations higher than 0.1mg/L caused more than 90% inhibition. The effect of carbaryl was less pronounced, achieving an 86% inhibition at concentrations corresponding to the 96-h LC50. After in vivo exposure to sublethal concentrations of parathion and azinphosmethyl (0.1 mg/L) and carbaryl (3.0 mg/L), the activity of the goldfish brain ChE was greatly reduced. In the following 96 h of recovery, the enzyme inhibited with carbaryl was restored to 75% activity, while the enzyme inhibited with organophosphates (OPs) required more than 35 days for recovery. Goldfish were able to withstand high percentages of brain ChE inhibition without mortality, suggesting that another target may be responsible for the lethal effects. However, the enzyme is a good biomarker of acute and subacute exposure to OPs and carbamates.

Acetylcholinesterase↗

PubMedDate not supplied

Assessment of azinphosmethyl exposure in California peach harvest workers.

We compared measurements of urinary alkylphosphate metabolites and oxime-induced reactivation of plasma cholinesterase (P-ChE) and erythrocyte acetylcholinesterase (RBC-AChE) with measurements of foliar residues, skin and clothing contamination, and P-ChE and RBC-AChE activities among 20 Northern California peach orchard workers exposed to the organophosphate agent azinphosmethyl (Guthion). Subjects entered orchards treated 30 d previously with azinphosmethyl and worked 21 d in treated fields during the ensuing 6 wk. Dislodgeable foliar residues ranged from 0.32-0.96 micrograms/cm2. Median reduction in RBC-AChE activity was 7% (p < .001) over the initial 3-d period of exposure and 19% (p < .01) over the 6-wk season. Urinary metabolites were the most sensitive indicator of recent exposure and correlated moderately with dermal and clothing levels (rs = +0.31-(+)0.55); urinary metabolites correlated well with RBC-AChE drawn 3 d after exposure began (rs = -0.77). No significant oxime-induced reactivation was found.

Acetylcholinesterase↗

PubMed2003

Susceptibility of leafrollers (Lepidoptera: Tortricidae) from organic and conventional orchards to azinphosmethyl, spinosad, and Bacillus thuringiensis.

Populations of obliquebanded leafroller, Choristoneura rosaceana Harris, and three-lined leafroller, Pandemis limitata Robinson, were obtained from seven sites in the Okanagan and Similkameen Valleys of British Columbia and assayed for their responses to three insecticides using a leaf disk bioassay. Lethal concentration ratios (LCRs) were calculated for all populations compared with a susceptible laboratory colony of C. rosaceana; significant variation was detected in response to all three insecticides. LCRs were 0.86-15.52 for azinphosmethyl, 0.38-2.37 for spinosad (Success), and 0.58-4.89 for Bacillus thuringiensis (Foray). Correlation analysis indicated no cross-resistance among the three insecticides. Leafroller populations obtained from apple orchards managed with organic production practices were more susceptible to azinphosmethyl than leafrollers obtained from conventionally managed sites. Conversely, the highest levels of tolerance to B. thuringiensis were observed in the populations from organic sites, possibly reflecting usage patterns; B. thuringiensis is one of the few insecticides allowed under organic production guidelines. All populations were highly susceptible to spinosad, which may be a useful tool for resistance management programs if used judiciously.

Animals↗

PubMed1975

Dislodgeable azinphosmethyl residues from air blast spraying of apple foliage in Ohio.

The distribution and decay rates of dislodgeable residues of azinphosmethyl applied by two types of air blast sprayers on apple foliage in Ohio were investigated. Leaf discs were taken from nine sites located on the periphery of Cortland apple trees at five dates after spraying. The sprayer delivering the higher airflow rate, but lower velocity, deposited the pesticide much more uniformly over the trees and applied more in the top of the tree. The other sprayer deposited the greatest proportion of pesticide on the site nearest the sprayer. The residue decreased at all sites and ranged from 42 to near 100% decrease at 14 days after spraying.

Agriculture↗

PubMed2003

Impact of dermal absorption factors in occupational exposure assessment: comparison of two models for agricultural reentry workers exposed to azinphosmethyl.

This analysis compares two deterministic reentry exposure models that differ in their treatment of the time dependence of dermal absorption. The first model, called the "traditional model," assumes that dermal absorption is a fixed fraction of the cumulative load on skin at the end of the workshift and that absorption is independent of residence time on the skin. The second model, called the "time-integrated model," incorporates the time dependence of both exposure and absorption by assuming that absorption begins at the outset of exposure and continues through the workshift and beyond, until an effective washing event occurs. These two models were evaluated using previously collected biological monitoring data from apple thinners exposed to azinphosmethyl. Daily doses predicted by the models were compared to doses estimated from the biological sampling results assuming pseudo steady-state excretion. The geometric mean dose estimated from the biological sampling data was 20 microg/kg/day. Corresponding geometric mean doses produced by the traditional model and the time-integrated model were 79 microg/kg/day and 24 microg/kg/day, respectively. When the doses predicted by the traditional model were plotted against those estimated from the biological measurements, the slope of the regression line was significantly greater than 1 (beta = 1.37). However, when this same analysis was conducted for the doses predicted by the time-integrated model, the confidence interval around the slope encompassed 1 (beta = 1.01). Thus, time-integrated treatment of absorption appeared to provide more realistic dose estimates than did the traditional approach.

Agriculture↗

PubMed1999

A toxicokinetic model to assess the risk of azinphosmethyl exposure in humans through measures of urinary elimination of alkylphosphates.

Azinphosmethyl (APM) is one of the most common insecticides used in fruit farming. The object of this paper is to develop a quick and practical test for assessing the risk for humans coming into contact with APM. It has been shown that the principal component of occupational and/or accidental exposure is through the skin (C. A. Franklin et al., 1981, J. Toxicol. Environ. Health 7, 715-731), but our approach is applicable to exposures via any route or a combination of routes. The method proposed in the present paper can accommodate a single-event exposure or repeated exposures over long periods. Urinary alkylphosphate (AP) metabolites are reliable bioindicators of the presence of APM in the body; they are easily accessible and can be used to estimate APM body burden. We developed a simple toxicokinetic model to link the time varying APM body burden to absorbed doses and to rates of elimination in the form of AP urinary metabolites. Using this model and data available in the literature, we are able to propose a "no observed adverse effect level" (NOAEL) for APM body levels and for corresponding absorbed doses. We have established that after a single exposure, the safe limit corresponding to the NOAEL is reached at a cumulative 0.215 mumoles AP/kg bw eliminated in urine in the first 24 hours following the beginning of exposure. For repeated daily exposures at steady state, the corresponding urinary AP metabolite level is equal to a cumulative 0.266 mumoles AP/kg bw eliminated per 24 hours.

Azinphosmethyl↗