N., and Bakry, N. M. (2006)

Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

A procedure for examining the feasibility of composting certain pesticides as a means for their disposal has been developed using a benchtop model compost system. This system is designed such that samples as small as 10 g can be studied, and, by using radiolabelled materials, compound transformation in compost media can be determined. Transformation of radiolabelled diazinon and chlordane has been examined using this procedure. After 3 weeks incubation under aerobic composting conditions (maximum temperature 65 [deg]C), 21.6% of the diazinon radiolabel was recovered from the volatile organics trap. Of this, 15.1% was solvent extractable and was identified by TLC as diazinon and the hydrolysis product 2-isopropyl-7-methyl-6-hydroxypyrimidine (IMHP). This hydrolysis product was the only radiolabelled form present in solvent extracts of the compost media. Radiolabelled chlordane was recovered as the unconverted alpha and gamma forms with 49.6% volatilized and 47.8% remaining in the compost media.

Pewnim, Thanit and Seifert, Josef (1993). Structural requirements for altering the L-tryptophan metabolism in mice by organophosphorous and methylcarbamate insecticides. European Journal of Pharmacology: Environmental Toxicology and Pharmacology 248: 237-241.
Chem Codes: Chemical of Concern: DZ Rejection Code: METABOLISM.

This study defined structural requirements for organophosphorous and methylcarbamate insecticides for altering the L-kynurenine pathway of L-tryptophan metabolism in mice. Kynurenine formamidase inhibition by organophosphorous acid triesters and methylcarbamates is the proposed primary event resulting in increase in xanthurenic acid urinary excretion and plasma L-kynurenine. Alteration of the L-kynurenine pathway occurred with compounds that inhibited liver kynurenine formamidase by more than 80%. Pyrimidinyl phosphorothioates followed by crotonamide phosphates were the most potent compounds that changed L-tryptophan metabolism, i.e., pirimiphos-ethyl (20 mg/kg) inhibited liver kynurenine formamidase by 99%, and increased xanthurenic acid urinary excretion and plasma L-kynurenine by 576 +/- 195 and 330 +/- 44%, respectively. Replacement of sulphur by oxygen in the phosphorothioate diazinon reduced in vivo liver kynurenine formamidase inhibition. Consequently, xanthurenic acid urinary excretion and plasma L-kynurenine were not elevated. Atropine, cycloheximide, 2-PAM and phenylmethylsulfonyl fluoride did not alleviate diazinon-altered L-tryptophan metabolism. Because of the potential of the majority of organophosphorous acid triesters and methylcarbamates to inhibit kynurenine formamidase, this novel noncholinergic mechanism warrants consideration in assessment of organophosphorous and methylcarbamate toxicity in occupational and accidental exposures. Noncholinergic actions/ Organophosphorous insecticides/ Methylcarbamate insecticides/ Kynurenine formamidase inhibition/ Xanthurenic acid (urinary excretion)/ Plasma L-kynurenine/ (Structural requirements)

Phillips, B. M., Anderson, B. S., Hunt, J. W., Nicely, P. A., Kosaka, R. A., Tjeerdema, R. S., De Vlaming, V., and Richard, N. (2004). In Situ Water and Sediment Toxicity in an Agricultural Watershed. Environ.Toxicol.Chem. 23: 435-442.
Chem Codes: Chemical of Concern: DZ,DPY Rejection Code: MIXTURE.

Phillips, P. J., Eckhardt, D. A., Freehafer, D. A., Wall, G. R., and Ingleston, H. H. (2002). Regional patterns of pesticide concentrations in surface waters of New York in 1997. Journal of the American Water Resources Association [J.Am.Water Resour.Assoc.].vol.38 of the American Water Resources Association [J. Am. Water Resour. Assoc.]. vol. 38888, no. 3, pp. 731-746. Jun 2002.: 731-746.

Chem Codes: SZ Rejection Code: NO SPECIES.

U.S. Geological Survey, 425 Jordan Road, Troy, New York 12180, USA, [mailto:[e-mail]]

The predominant mixtures of pesticides found in New York surface waters consist of five principal components. First, herbicides commonly used on corn (atrazine, metolachlor, alachlor, cyanazine) and a herbicide degradate (deethylatrazine) were positively correlated to a corn-herbicide component, and watersheds with the highest corn-herbicide component scores were those in which large amounts of row crops are grown. Second, two insecticides (diazinon and carbaryl) and one herbicide (prometon) widely used in urban and residential settings were positively correlated to an urban/residential component. Watersheds with the highest urban/residential component scores were those with large amounts of urban and residential land use. A third component was related to two herbicides (EPTC and cyanazine) used on dry beans and corn, the fourth to an herbicide (simazine) and an insecticide (carbaryl) commonly used in orchards and vineyards, and the fifth to an herbicide (DCPA). Results of this study indicate that this approach can be used to: (1) identify common mixtures of pesticides in surface waters, (2) relate these mixtures to land use and pesticide applications, and (3) indicate regions where these mixtures of pesticides are commonly found
English

Phillips, P. J., Eckhardt, D. A., Freehafer, D. A., Wall, G. R., and Ingleston, H. H. (2002). Regional patterns of pesticide concentrations in surface waters of New York in 1997. Journal of the American Water Resources Association [J.Am.Water Resour.Assoc.].vol.38 of the American Water Resources Association [J. Am. Water Resour. Assoc.]. vol. 38888, no. 3, pp. 731-746. Jun 2002.: 731-746.

Chem Codes: Chemical of Concern: DEATZ Rejection Code: NO SPECIES.

U.S. Geological Survey, 425 Jordan Road, Troy, New York 12180, USA, [mailto:[e-mail]]

The predominant mixtures of pesticides found in New York surface waters consist of five principal components. First, herbicides commonly used on corn (atrazine, metolachlor, alachlor, cyanazine) and a herbicide degradate (deethylatrazine) were positively correlated to a corn-herbicide component, and watersheds with the highest corn-herbicide component scores were those in which large amounts of row crops are grown. Second, two insecticides (diazinon and carbaryl) and one herbicide (prometon) widely used in urban and residential settings were positively correlated to an urban/residential component. Watersheds with the highest urban/residential component scores were those with large amounts of urban and residential land use. A third component was related to two herbicides (EPTC and cyanazine) used on dry beans and corn, the fourth to an herbicide (simazine) and an insecticide (carbaryl) commonly used in orchards and vineyards, and the fifth to an herbicide (DCPA). Results of this study indicate that this approach can be used to: (1) identify common mixtures of pesticides in surface waters, (2) relate these mixtures to land use and pesticide applications, and (3) indicate regions where these mixtures of pesticides are commonly found
English

Phipps, G. L. (1988). Diazinon Acute Tests for Criteria Development. April 29th Memo to R.Spehar, U.S.EPA, Duluth, MN 2 p.

EcoReference No.: 69471

Chemical of Concern: DZ; Habitat: A; Effect Codes: MOR; Rejection Code: NO ABSTRACT.

Phipps, G. L., Harden, M. J., Leonard, E. N., Roush, T. H., Spehar, D. L., Stephan, C. E., Pickering, Q. H., and Buikema, A. L. J. (1984). Effects of Pollution on Freshwater Organisms. J.Water Pollut.Control Fed. 56: 725-758.

Chem Codes: EcoReference No.: 53156
Chemical of Concern: EDT,AND,Al,NH,PAH,Sb,As,ATZ,Ba,BNZ,BZD,Be,Cd,CBL,CTC,CHD,Cl,Cl2,CPY,Cr,Co,Cu,CN,DDT,DZ,CBZ,CPH,DLD,ES,EN,FA,HPT,HCCH,HCCP,Fe,ISO,Pb,Mn,Hg,Mo,NAPH,Ni,NBZ,NP,PCB,PRN,PNB,PCP,PL,Se,Ag,SZ,TCDD,TOL,TXP,V,Zn Rejection Code: REFS CHECKED/REVIEW.

Pickering, Q. H., Henderson, C., and Lemke, A. E. (1962). The Toxicity of Organic Phosphorus Insecticides to Different Species of Warmwater Fishes. Trans.Am.Fish.Soc. 91: 175-184.

EcoReference No.: 2893

Chemical of Concern: MP,MLN,AZ,PRN,DZ,DEM; Habitat: A; Effect Codes: MOR; Rejection Code: NO CONTROL(ALL CHEMS).

Pierdet, Andre, Nedelec, Lucien, Delaroff, Vladimir, and Allais, Andre (1980). Synthese totale de la (+/-) negamycine. Tetrahedron 36: 1763-1772.

Chem Codes: Chemical of Concern: DZ Rejection Code: METHODS.

ResumeUne synthese totale de la (+/-) negamycine 1 a ete realise en 14 stades a partir du dimere de l'acroleine qui possede le squelette carbone necessaire a l'edification de la lactone intermediaire 4. Le traitement de l'acetoxy-methyl-2 dihydro-3,4[2H]pyranne 8, provenant de 6, par le tetracetate de plomb conduit a l'hemiacetal allylique 15, qui est transforme en ethers methyliques anomeres correspondants 23. L'hydroxylation de la double liaison de 23 par l'acetate mercurique s'effectue selectivement en position [gamma] pour donner les alcools isomeres 24 qui sont isols sous forme des dimesylates 25a et 25b. La condensation de l'azoture de sodium sur le derive trans 25a fournit le diazide cis 26a par inversion de la configuration en C3. L'hydrogenation de 26a suivie de l'acetylation de la diamine intermediaire non isolee conduit alors au diamide 28 ayant la stereochimie attendue. Par oxydation de l'hemicetal correspondant 29 avec le silicate d'argent, on obtient la diacetamido lactone 4, qui est ensuite hydrolysee en (+/-) [delta]-hydroxy [beta]-lysine 2 par reflux dans HCl dilue. La protection des fonctions aminees de 2 sous forme de benzylcarbamates est accompagnee de cyclisation en lactone 30. Cependant, celle-ci, traitee par l'ester benzylique de l'acide N-methylhydrazinoacetique en presence de silice conduit directement a l'hydrazine 36, puis a la (+/-) negamycine apres hydrogenolyse des groupements protecteurs. Les activits antibacteriennes de l'antibiotique racemique ont ete comparees in vitro et in vivo a celles du produit natural et de la gentamicine C.

Pisani-Borg, E., Cuany, A., Brun, A., Amichot, M., Fournier, D., and Berge, J. B. (1996). Oxidative Degradation of Diazinon byDrosophila:Metabolic Changes Associated with Insecticide Resistance and Induction. Pesticide Biochemistry and Physiology 54: 56-64.
Chem Codes: Chemical of Concern: DZ Rejection Code: FATE.

Using [14C]diazinon, it was found that four molecules accounted for most of the metabolites afterin vitroorin vivoincubation withDrosophila melanogaster.RalDDTR, an insecticide-resistant strain ofDrosophila,produced higher amounts of each metabolite than CantonS, a susceptible strain. However, the degradative metabolic pathway giving hydroxydiazinon and pyrimidine was twofold faster than the activating metabolic pathway giving hydroxydiazoxon and diazoxon. Clofibrate and phenobarbital increased the metabolism of diazinon in induced, susceptible flies. Phenobarbital was more potent than clofibrate in stimulating the hydroxylation of diazinon. Kinetic analysis ofin vivoinhibition of brain acetylcholinesterase by diazinon or hydroxydiazinon demonstrated that degradation of diazinon, especially in RalDDTR, was delayed compared to the degradation of hydroxydiazinon. Varying levels of diazinon tolerance amongDrosophilastrains may be explained by differential metabolic pathways. The most conclusive result was a strong interaction between tolerance and the rate of formation of hydroxylated derivatives.

PLANAS, C., CAIXACH, J., SANTOS FJ, and RIVERA, J. (1997). Occurrence of pesticides in Spanish surface waters. Analysis by high resolution gas chromatography coupled to mass spectrometry. CHEMOSPHERE; 34 2393-2406.
Chem Codes: Chemical of Concern: DZ Rejection Code: SURVEY.

BIOSIS COPYRIGHT: BIOL ABS. A general study of the presence of pesticides in Spanish surface waters was carried out. A total of 97 samples were analysed by liquid-liquid extraction followed by HRGC in full scan mode. This procedure allows the detection and identification of several commonly used pesticides at levels of 5-50ng/L. The results obtained are studied with regard to know the most common pesticides found in Spanish surface waters, the percentage of them proposed to be included in the Directive 76/464/EEC and their variability depending on the area (agricultural or industrial) and the period of sampling./GROWTH & DEVELOPMENT Ecology/ Oceanography/ Fresh Water/ Biophysics/ Macromolecular Systems/ Molecular Biology/ Air Pollution/ Soil Pollutants/ Water Pollution/ Plants/Growth & Development/ Soil/ Herbicides/ Pest Control/ Pesticides

PLANT JW, HORTON BJ, ARMSTRONG, R. TF, and CAMPBELL NJ (1999). Modelling pesticide residues on greasy wool: Using organophosphate and synthetic pyrethroid survey data. AUSTRALIAN JOURNAL OF EXPERIMENTAL AGRICULTURE; 39 9-19.
Chem Codes: Chemical of Concern: DZ Rejection Code: SURVEY.

BIOSIS COPYRIGHT: BIOL ABS. Several surveys have examined the relationship between organophosphate and synthetic pyrethroid residues in wool and associated treatments. These have been combined and summarised using a model of on-farm survey data. The model estimated the amount of chemical taken up by the wool at application. This was based on experimental breakdown rates of these pesticides on wool determined in controlled trials. For about 10% of survey results the chemical measured on the wool did not match the chemical t The wide variation in results suggests that some producers may apply excessive amounts of pesticides while others use too little to have a useful effect. The model estimated the amount of pesticide taken up by the fleece using the residue left at shearing and the known breakdown rate for a given method and chemical group. When organophosphates were applied by dipping, the amount of chemical taken up by the fleece appeared to increase as the length of the wool increased. This was Poisoning/ Animals, Laboratory/ Animal Husbandry/ Herbicides/ Pest Control/ Pesticides/ Artiodactyla

Poet, T. S., Kousba, A. A., Dennison, S. L., and Timchalk, C. (2004). Physiologically Based Pharmacokinetic/Pharmacodynamic Model for the Organophosphorus Pesticide Diazinon. NeuroToxicology 25: 1013-1030.
Chem Codes: Chemical of Concern: DZ Rejection Code: MODELING.

Diazinon (DZN) is an organophosphorus pesticide with the possibility for widespread exposures. The toxicological effects of DZN are primarily mediated through the effects of its toxic metabolite, DZN-oxon on acetylcholinesterases, which results in accumulation of acetylcholine at neuronal junctions. A physiologically based pharmacokinetic/pharmacodynamic (PBPK/PD) model was developed to quantitatively assess the kinetics of DZN and its metabolites in blood and the inhibition of cholinesterases in plasma, RBC, brain, and diaphragm. Focused in vivo pharmacokinetic studies were conducted in male Sprague-Dawley rats and the data were used to refine the model. No overt toxicity was noted following doses up to 100 mg/kg. However, cholinesterases in plasma, RBC, brain and diaphragm were substantially inhibited at doses of 50 mg/kg. In plasma, total cholinesterase was inhibited to less than 20% of control by 6 h post dosing with 100 mg/kg. Inhibition of brain acetylcholinesterase (AChE) following 100 mg/kg exposures was approximately 30% of control by 6 h. Diaphragm butyrylcholinesterase (BuChE) inhibition following 100 mg/kg dosing was to less than 20% of control by 6 h. The PBPK/PD model was used to describe the concentrations of DZN and its major, inactive metabolite, 2-isopropyl-4-methyl-6-hydroxypyrimidine (IMHP) in plasma and urinary elimination of IMHP. The fit of the model to plasma, RBC, brain, and diaphragm total cholinesterase and BuChE activity was also assessed and the model was further validated by fitting data from the open literature for intraperitoneal, intravenous, and oral exposures to DZN. The model was shown to quantitatively estimate target tissue dosimetry and cholinesterase inhibition following several routes of exposures. This model further confirms the usefulness of the model structure previously validated for chlorpyrifos and shows the potential utility of the model framework for other related organophosphate pesticides. Organophosphate pesticide/ PBPK/PD/ Cholinesterase inhibition

Poet, T. S., Wu, H., Kousba, A. A., and Timchalk, C. (2003). In Vitro Rat Hepatic and Intestinal Metabolism of the Organophosphate Pesticides Chlorpyrifos and Diazinon. Toxicological Sciences [Toxicol. Sci.]. Vol. 72, no. 2, pp. 193-200. 2003.
Chem Codes: Chemical of Concern: DZ Rejection Code: IN VITRO.

ISSN: 1096-6080

Descriptors: Pesticides (organophosphorus)
Descriptors: Chlorpyrifos
Descriptors: Diazinon
Descriptors: Liver
Descriptors: Intestine
Abstract: Chlorpyrifos (CPF) and diazinon (DZN) are thionophosphorus organophosphate (OP) insecticides; their toxicity is mediated through CYP metabolism to CPF-oxon and DZN-oxon, respectively. Conversely, CYPs also detoxify these OPs to trichloropyridinol (TCP) and 2-isopropyl-4-methyl-6-hydroxypyrimidine (IMHP), respectively. In addition, A-esterase (PON1) metabolism of CPF- and DZN-oxon also forms TCP and IMHP. This study evaluated the role intestinal and hepatic metabolism may play in both the activation and detoxification of CPF and DZN in Sprague-Dawley rats. Similar CYP- and PON1-mediated metabolic profiles were demonstrated in microsomes from liver or isolated intestinal enterocytes. The metabolic efficiency was estimated by calculating the psuedo-1st order rate constant from the metabolic constants by dividing V sub(max)/K sub(m). In enterocyte microsomes, the CYP metabolic efficiency for metabolism to the oxon metabolites was ~28-fold greater for CPF than DZN. Compared on a per nmol P450 basis, the V sub(max) for CPF in enterocytes was ~2-3 times higher than in liver microsomes for the production of CPF-oxon and TCP. The Michaelis-Menten rate constant (K sub(m)) for the metabolism of CPF to CPF-oxon was comparable in liver and enterocyte microsomes; however, the enterocyte K sub(m) for TCP production was higher (indicating a lower affinity). The smaller volume of intestine, lower amount of CYP, and higher K sub(m) for TCP in the enterocyte microsomes, resulted in a lower catalytic efficiency (2 and 62 times) than in liver for oxon and TCP. PON1-mediated metabolism of CPF- and DZN-oxon was also demonstrated in liver and enterocyte microsomes. Although PON1 affinity for the substrates was comparable in hepatic and enterocytic microsomes, the V sub(max) were 48- to 275-fold higher, in the liver. These results suggest that intestinal metabolism may impact the metabolism of CPF and DZN, especially following low-dose oral exposures.
Language: English
English
Publication Type: Journal Article
Classification: X 24133 Metabolism
Subfile: Toxicology Abstracts

Pogacnik, L. and Franko, M. (1999). Determination of organophosphate and carbamate pesticides in spiked samples of tap water and fruit juices by a biosensor with photothermal detection. Biosensors & Bioelectronics 14 : 569-578.

Chem Codes: CBF Rejection Code: METHODS/NO TOX DATA/FOOD.

ABSTRACT: BIOSIS COPYRIGHT: BIOL ABS. The determination of organophosphate (paraoxon, chlorpyrifos, diazinon) and carbamate (carbaryl, carbofuran) pesticides in spiked drinking water and fruit juices was carried out using a photothermal biosensor. The biosensor consists of a cartridge containing immobilised enzyme acetylcholinesterase (AChE) placed in a flow-injection analysis (FIA) manifold and a photothermal detector based on thermal lens spectrometry. With this approach, 0.2 ng/ml of paraoxon can be detected in less than 15 min. raoxon in tap water, orange juice and apple juice were obtained, respectively.

KEYWORDS: Biochemical Methods-General
KEYWORDS: Biochemical Studies-General
KEYWORDS: Biophysics-Bioengineering
KEYWORDS: Enzymes-Methods
KEYWORDS: Food Technology-General
KEYWORDS: Toxicology-General
KEYWORDS: Toxicology-Foods
KEYWORDS: Toxicology-Environmental and Industrial Toxicology
KEYWORDS: Pest Control

POLETIKA NN, HAVENS PL, ROBB CK, and SMITH RD (1998). ORGANOPHOSPHOROUS INSECTICIDE CONCENTRATION PATTERNS IN AN AGRICULTURALLY DOMINATED TRIBUTARY OF THE SAN JOAQUIN RIVER. 215TH AMERICAN CHEMICAL SOCIETY NATIONAL MEETING, DALLAS, TEXAS, USA, MARCH 29-APRIL 2, 1998. ABSTRACTS OF PAPERS AMERICAN CHEMICAL SOCIETY; 215 AGRO 41.

Chem Codes: Chemical of Concern: DZ Rejection Code: ABSTRACT.

BIOSIS COPYRIGHT: BIOL ABS. RRM MEETING ABSTRACT ORGANOPHOSPHOROUS CONCENTRATION PATTERN INSECTICIDE PESTICIDES FRESHWATER ECOLOGY TRIBUTARY SAN JOAQUIN RIVER CALIFORNIA USA Congresses/ Biology/ Ecology/ Biochemistry/ Herbicides/ Pest Control/ Pesticides

Pope, L. M. and Putnam, J. E. ( Effects of urbanization on water quality in the Kansas River, Shunganunga Creek basin and Soldier Creek, Topeka, Kansas, October 1993 through September 1995.
Chem Codes: SZ Rejection Code: HUMAN HEALTH.

A study of urban-related water-quality effects in the Kansas River, Shunganunga Creek Basin and Soldier Creek in Topeka, Kansas, was conducted from October 1993 through September 1995. The purpose of this report is to assess the effects of urbanization on instream concentrations of selected physical and chemical constituents within the city of Topeka. A network of seven sampling sites was established in the study area. Samples principally were collected at monthly intervals from the Kansas River and from the Shunganunga Creek Basin and at quarterly intervals from Soldier Creek. The effects of urbanization were statistically evaluated from differences in constituent concentrations between sites on the same stream. No significant differences in median concentrations of dissolved solids, nutrients, or metals and trace elements, or median densities of fecal bacteria were documented between sampling sites upstream and downstream from the major urbanized length of the Kansas River in Topeka. Discharge from the city's primary wastewater-treatment plant is the largest potential source of contamination to the Kansas River This discharge increased concentrations of dissolved ammonia, total phosphorus and densities of fecal bacteria. Calculated dissolved ammonia as nitrogen concentrations in water from the Kansas River ranged from 0.03 to 1.1 milligrams per liter after receiving treatment-plant discharge. However, most of the calculated concentrations were considerably less than 50 percent of Kansas Department of Health and Environment water-quality criteria, with a median value of 20 percent. Generally, treatment-plant discharge increased calculated total phosphorus concentrations in water from the Kansas River by 0.01 to 0.04 milligrams per liter, with a median percentage increase of 7.6 percent. The calculated median densities of fecal coliform and fecal Streptococci bacteria in water from the Kansas River increased from 120 and 150 colonies per 100 milliliters of water, respectively, before treatment-plant discharge to a calculated 4,900 and 4,700 colonies per 100 milliliters of water, respectively, after discharge. Median concentrations of dissolved solids were not significantly different between three sampling sites in the Shunganunga Creek Basin. Median concentrations of dissolved nitrate as nitrogen, total phosphorus and dissolved orthophosphate were significantly larger in water from the upstream-most Shunganunga Creek sampling site than in water from either of the other sampling sites in the Shunganunga Creek Basin probably because of the site's proximity to a wastewater-treatment plant. Median concentrations of dissolved nitrate as nitrogen and total phosphorus during 1993-95 at upstream sampling sites were either significantly larger than during 1979-81 in response to increase of wastewater-treatment plant discharge or smaller because of the elimination of wastewater-treatment plant discharge. Median concentrations of dissolved ammonia as nitrogen were significantly less during 1993-95 than during 1979-81. Median concentrations of total aluminum, iron, maganese and molybdenum were significantly larger in water from the downstream-most Shunganunga Creek sampling site than in water from the upstream-most sampling site. This probably reflects their widespread use in the urban environment between the upstream and downstream Shunganunga Creek sampling sites. Little water-quality effect from the urbanization was indicated by results from the Soldier Creek sampling site. Median concentrations of most water-quality constituents in water from this sampling site were the smallest in water from any sampling site in the study area. Herbicides were detected in water from all sampling sites. Some of the more frequently detected herbicides included acetochlor, alachlor, atrazine, cyanazine, EPTC, metolachlor, prometon, simazine and tebuthiuron. Detected insecticides including chlordane, chlorpyrifos, Diazinon, lindane and malathion. However, no concentrations exceeded Kansas Department of Health and Environment ambient water-quality criteria USGS Water-Resources Investigations Report. 84 pp