Abstracts
Dithiopyr
CAS No. 97886-45-8
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Adverse Effects

ACTIVITY: Herbicide (pyridine)

CAS Name: S,S?-dimethyl 2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate

Structure:

Reports available from
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NTIS/OTS0537216


1992 - INITIAL SUBMISSION: ACUTE TOXICITY OF MON 7200 TO COMMON CARP WITH COVER LETTER DATED 04-06-92

CHEM BIOTESTING CTR
:

MONSANTO AG CO
MON 7200
ENVIRONMENTAL EFFECTS
ACUTE TOXICITY
FISH-FRESHWATER

97886-45-8 EPA/OTS; Doc #88-920001753
NTIS/OTS0555009 1992 - INITIAL SUBMISSION: LETTER FROM MONSANTO CO TO USEPA REGARDING TOXICITY STUDIES WITH COVER LETTER DATED 08/25/92 MONSANTO CO
VARIOUS
HEALTH EFFECTS
SUBCHRONIC TOXICITY
MAMMALS
RABBITS
DERMAL
ENVIRONMENTAL EFFECTS
ACUTE TOXICITY
FISH-FRESHWATER
ORAL
GAVAGE
REPRODUCTION/FERTILITY EFFECTS
TERATOGENICITY

RATS
ENVIRONMENTAL FATE
PHYSICAL/CHEMICAL PROPERTIES
PARTITION COEFFICIENT
9016-45-9
34256-82-1
56516-72-4
57415-63-1
61791-26-2
97886-45-8
EPA/OTS; Doc #88-920008191
NTIS/OTS0540049

1992 - INITIAL SUBMISSION: 4-WEEK ORAL TOXICITY STUDY WITH MON 7200 IN RATS (FINAL REPORT) WITH COVER LETTER DATED 05-28-92

INST OF ENVIRONMNTL TOXICOLOGY

MONSANTO CO
MON 7200
HEALTH EFFECTS
SUBCHRONIC TOXICITY
MAMMALS
RATS
ORAL
DIET
97886-45-8 EPA/OTS; Doc #88-920003398

From Toxline at Toxnet

J PESTIC SCI; 18 (2). 1993. S91-S97.

SUMMARY OF TOXICOLOGY STUDIES WITH DITHIOPYR

WARD DP

BIOSIS COPYRIGHT: BIOL ABS. RRM TURF GRASS RICE PLANT AGRICHEMICAL MOLECULAR STRUCTURE CROP INDUSTRY HERBICIDE TOXICITY STANDARDS


Xenobiotica, Vol. 21, No. 10, pages 1265-1271, 9 references, 1991

In Vitro Transformation of Dithiopyr by Rat Liver Enzymes: Conversion of Methylthioesters to Acids by Oxygenases

Feng PCC, Solsten RT

The objective of this study was to elucidate the pathway of transformation of dithiopyr (97886-45-8) to acidic metabolites. The in-vitro metabolism of dithiopyr by male rat liver enzyme preparations was examined. Microsomal, cytosolic and S9 fractions were prepared from livers of male Long-Evans-rats. The liver enzymes transformed dithiopyr into the corresponding monoacids as the predominant metabolites. The rat liver microsomal oxygenases but not the esterases mediated this transformation. The monoacid on the CF2 side of dithiopyr was produced at about five times the concentration of the monoacid on the CF3 side. The mechanism of monoacid formation is believed to proceed through an initial sulfur oxidation of the methylthioester group and a subsequent nucleophilic displacement reaction. A hydrolytic process is not thought to be important in this regard. The authors propose that the methylthioester groups in dithiopyr are activated via oxidation of the sulfur atoms. The resulting unstable sulfoxide intermediate is subjected to nucleophilic displacement by hydroxide or glutathione anions to produce the observed monoacids or GSH conjugate. A second metabolic pathway was predicted to be S-demethylation by cytochrome-P-450 enzymes to form the thioacid, which was not detected as a metabolite under in-vitro conditions.

 

Full free study available at http://jeq.scijournals.org/cgi/content/full/30/1/18

J Environ Qual. 2001 Jan-Feb;30(1):18-23.
 
In vitro pesticide degradation in turfgrass soil incubated under open and sealed conditions.

Suzuki T, Yaguchi K, Suzuki S, Suga T.

Tama Branch Lab, Tachikawa, Tokyo, Japan. tsuzuki@tokyo-eiken.go.jp

Degradation of selected pesticides was conducted in a turfgrass soil from a golf course under open (i.e., allowing gas exchange with atmosphere) and sealed systems. The time required for 50% of the initial dose of fenitrothion (O,O-dimethyl O-4-nitro-m-tolyl phosphorothioate), diazinon (O,O-dimethyl O-2-isopropyl-6-methylpyrimidin4-yl phosphorothioate), iprodione [3-(3,5-dichlorophenyl)-N-isopropyl-2,4-dioxo-imidazolidine-1-carboxamide], mecoprop [(RS)-2-(4-chloro-otolyloxy)propionic acid], and asulam (4-aminophenylsulfonyl-carbamate) to dissipate (half-life, t 1/2) was less than 2 wk under both conditions. The t 1/2 values of dithiopyr (S,S'-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoro-methylpyridine-3,5-dicarbothioate) were 324 and 185 d under the open and sealed conditions, respectively. The t 1/2 values of isoprothiolane (di-isopropyl 1,3-dithiolan-2-ylidene-malonate), flutolanil (alpha,alpha,alpha-trifluoro-3'-isopropoxy-o-toluanilide), and benefin (N-butyl-N-ethyl-alpha,alpha,alpha-trifluoro-2,6-dinitro-p-toluidine) under the open conditions were 154, 336, and 47 d, respectively. The t 1/2 values of these pesticides increased slightly under the sealed conditions. The t 1/2 values of terbutol (2,6-di-tert-butyl-4-methylphenyl N-methycarbamate) and one of the major degradation products, N-demethyl-terbutol (2,6-di-tert-butyl-4-methylphenyl carbamate), were 182 and 291 d under the open conditions and increased by six- and threefold under the sealed conditions, respectively. The degradation system under the sealed conditions could characterize the persistence of terbutol and N-demethyl-terbutol, which were the most persistent in the field.


From Toxline at Toxnet

JOURNAL OF ENVIRONMENTAL QUALITY; 26 (2). 1997. 379-386.

Potential movement of dithiopyr following application to golf courses.

HONG S, SMITH AE

Dep. Crop Soil Sci., Univ. Ga., Ga. Exp. Stn., Griffin, GA 30223, USA.

BIOSIS COPYRIGHT: BIOL ABS. Research was conducted to evaluate the potential movement of dithiopyr (S,S-dimethyl2-(difluoromethyl)-4-(2-methylpropyl)-6(trifluoromethyl)-3,5-pyridinedicarbothioate) from golf courses. Dithiopyr was applied as granule and emulsifiable concentrate (EC) formulations to 'Penncross' creeping bentgrass (Agrostis stolonifera L.) and 'Tifdwarf' hybrid bermudagrass (Cynodon dactylon (L.) Pers. Burtt-Davy) in simulated greens. Less than 0.6% of the dithiopyr was transported through the rooting media (a mixture containing at least 97% coarse sand by weight with sphagnum peat moss). Dithiopyr concentrations in the leachate, transported through the greens, did not exceed 3 mug L-1. Most of the dithiopyr (11-31%) was detected in the top 0 to 12.5 cm of rooting media at the end of the greenhouse experiments and as much as 20% of the applied dithiopyr was removed with the leaf clippings over the duration of the greenhouse experiments. The highest concentration of dithiopyr transpo [absract truncated]


From Toxline at Toxnet

203RD ACS (AMERICAN CHEMICAL SOCIETY) NATIONAL MEETING, SAN FRANCISCO, CALIFORNIA, USA, APRIL 5-10, 1992. ABSTR PAP AM CHEM SOC; 203 (1-3). 1992. AGRO130.

POTENTIAL LEACHING OF HERBICIDES APPLIED TO GOLF COURSE GREENS

SMITH AE


BIOSIS COPYRIGHT: BIOL ABS. RRM 2 4-D DITHIOPYR DICAMBA PEST CONTROL WATER INFILTRATION PERCOLATION

CAS Registry Numbers:
97886-45-8
97886-45-8

1918-00-9
94-75-7


From Toxline at Toxnet

PROTOPLASMA; 179 (1-2). 1994. 16-25.

Mitotic disrupter herbicides act by a single mechanism but vary in efficacy.

HOFFMAN JC, VAUGHN KC

Southern Weed Sci. Lab., ARS, U.S. Dep. Agric., P.O. Box 350, Stoneville, MS 38776, USA.

BIOSIS COPYRIGHT: BIOL ABS. Although there are numerous herbicides that disrupt mitosis as a mechanism of action, to date not one has compared the effects of these disrupters on a single species and over a range of concentrations. Oat seedlings, treated with a range of concentrations of nine different "mitotic disrupter herbicides", were examined by immunofluorescence microscopy of tubulin in methacrylate sections. All herbicides caused the same kinds of microtubule disruption, although the concentrations required to cause the effects differed markedly between the herbicides. Effects on spindle and phragmoplast mitotic microtubule arrays were seen at the lowest concentrations and manifested as multipolar spindles and bifurcated phragmoplasts (which subsequently resulted in abnormal cell plate formation). At increasing concentrations, effects on mitotic microtubule arrays manifested as microtubule tufts at kinetochores and reduction of cortical microtubules resulting in arrested prometaphase figure

CAS Registry Numbers:
97886-45-8
97886-45-8

23950-58-5
19044-88-3
16118-49-3
8066-92-0
3337-71-1
1918-11-2
1861-32-1
1582-09-8
122-42-9
101-27-9
101-21-3


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1958076&dopt=Abstract

Arch Environ Contam Toxicol. 1991 Aug;21(2):195-201.

Assessment of lawn care worker exposure to dithiopyr.

Cowell JE, Lottman CM, Manning MJ.

Monsanto Agricultural Company, Environmental Science Department, St. Louis, Missouri 63198.

Eighteen ChemLawn lawn care specialists were monitored for worker exposure by both passive dosimetry and biological monitoring techniques in the performance of normal duties of mixing/loading and application of Dimension herbicide to turfgrass. Passive dosimetry was performed, utilizing cotton gauze patches, silica gel air sampling absorption media, and hand washes as per US Environmental Protection Agency Pesticide Assessment Guidelines. Biological monitoring was performed by analysis of all urine specimens collected from each specialist from initiation until 72 h after application of dithiopyr. The mean body dose estimate from urinalysis of the specimens collected over the 72 h period was 4.60 x 10(-5) mg/kg/lb applied. The passive dosimetry body dose estimates using dermal deposition measurements corrected for skin penetration and simulated inhalation measurements were calculated for the two clothing scenarios observed in the worker tests. The mean body dose estimate for a fully clothed specialist wearing a long-sleeved shirt was 8.09 x 10(-5) mg/kg/lb while for a specialist wearing a short-sleeved shirt the estimate was 3.62 x 10(-4) mg/kg/lb. The lower leg regions, which were protected by long pants and boots, had the highest exposure by passive dosimetry data.

PMID: 1958076 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=1796604&dopt=Abstract

Xenobiotica. 1991 Oct;21(10):1265-71.

In vitro transformation of dithiopyr by rat liver enzymes: conversion of methylthioesters to acids by oxygenases.

Feng PC, Solsten RT.

Monsanto Agricultural Co., A Unit of Monsanto Co., St. Louis, MO 63198.

1. Transformation of dithiopyr by rat liver enzymes in vitro produced the corresponding monoacids as the predominant metabolites.
2. Transformations of the methylthioester functional groups in dithiopyr to the monoacids were mediated via rat liver microsomal oxygenases, and not via esterases.
3. Based on the formation of a dithiopyr-glutathione conjugate, the mechanism of monoacid formation is believed to proceed through an initial sulphur oxidation of the methylthioester group and a subsequent nucleophilic displacement reaction.

PMID: 1796604 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12558106&dopt=Abstract

Pest Manag Sci. 2003 Jan;59(1):114-8.

Dissipation of the herbicide dithiopyr in soil and residues in wheat (Triticum aestivum L) grain under Indian tropical conditions.

Saikia N, Kulshrestha G.

Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi, India.

Dissipation of dithiopyr in soil was monitored after application to wheat crop as pre- or post-emergence applications at two rates, viz 100 and 200 g AI ha(-1). The level of dithiopyr in the soil was assessed by gas chromatography, and its disappearence was found to follow a first-order decay curve irrespective of rate or method of application. The half-life in soil ranged between 17.3 and 25.0 days and residues at harvest (150 days after application) ranged between 4.0 and 8.8% of amounts applied. Investigation of microbial degradation of dithiopyr was conducted in minimal salt and Czapek Dox media in which 80% of the compound degraded within 15 days. Residues were not detected in wheat grain at harvest.

PMID: 12558106 [PubMed - in process]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=12403267&dopt=Abstract

J Environ Sci Health B. 2002 Nov;37(6):573-86.

Adsorption-desorption, persistence, and leaching behavior of dithiopyr in an alluvial soil of India.

Gupta S, Gajbhiye VT.

Division of Agricultural Chemicals, Indian Agricultural Research Institute, New Delhi.

Investigations were undertaken to determine the adsorption-desorption, persistence and leaching of dithiopyr (S,S'-dimethyl 2-difluoromethyl-4-isobutyl-6-trifluoromethyl pyridine-3,5-dicarbothioate) in an alluvial soil under laboratory condition. The adsorption-desorption studies were carried out using batch equilibration technique. The mass balance studies showed that 83-97% of the pesticide was recovered during adsorption-desorption studies. The results revealed strong adsorption of dithiopyr in alluvial soil with Kd values ranging from 3.97-5.78 and Freundlich capacity factor (KF) value of 2.41. The strong adsorption was evident from the hysteresis effect observed during desorption. The hysteresis coefficients ranged from 0.17-0.40. The persistence studies were carried out at two concentrations (1.0 and 10.0 microg g(-1) level) under field capacity moisture and submerged condition by incubating the treated soil at 25 +/- 1 degrees C. In general, dithiopyr persisted beyond 90 days with half-life varying from 11.5-12.9 days under different conditions. The rate of application and moisture regimes had no overall effect on the persistence. The leaching studies carried out in packed column under saturated flow condition revealed that dithiopyr was highly immobile in alluvial soil. Only small amounts (0.02-0.04%) were recovered from leachate whereas major portion (99.9%) remained in top layer of the soil column. The data suggest that strong adsorption of dithiopyr will cause a greater persistence problem in the soil. However, the chances of its movement to ground water will be negligible due to its immobility.

PMID: 12403267 [PubMed - indexed for MEDLINE]


http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11599718&dopt=Abstract

J Environ Sci Health B. 2001 Sep;36(5):529-43.

Sorption and mobility of dithiopyr in golf course greens rooting medium.

Hong S, Smith AE.

Department of Crop and Soil Sciences, College of Agricultural and Environmental Sciences, The University of Georgia, Georgia Experiment Station, Griffin 30223, USA. sh87@cornell.edu

Sorption and mobility of dithiopyr in golf course greens rooting medium (RM) were studied. The sorption increased from 20 to 27 degrees C at 24 h after treatment (HAT) and reached equilibrium in 48 HAT at 20 degrees C. The sorption isotherms had Freundlich values (KF) of 1122, 27.44 to 35.16, and 0.053 to 0.168 for peat moss, the RM, and quartz sand, respectively, and solid to aqueous phase partition coefficients (Kd) of 470 to 1706 L/kg, 14.61 to 84.4 L/kg, and 0.07 to 0.29 L/kg for peat moss, RM, and quartz sand, respectively. Generally, higher dithiopyr concentration in the aqueous solution and the reduced pH of the solution corresponded to the higher Kd values. The average values for dispersion (D, cm2/min), retardation coefficient (R), beta, and omega parameters for solute transport in the RM lysimeter; obtained from CXTFIT curve fitting of Br- breakthrough curves; were 0.95, 1.01, 1, and 93.89, respectively. After elutriation by 18 L of aqueous KNO3 (10 mM), greater than 90% of the added dithiopyr remained in the top 10 cm of the RM lysimeter and no detectable dithiopyr was present at depths beyond 35 cm. The lysimeter effluent contained dithiopyr at concentrations less than 3.5 microg/L. The R value obtained from CXFIT curve fitting is 38.5. Results from both sorption and mobility experiments indicated that dithiopyr is quite immobile in golf course greens RM and has minimal potential for movement into surface water drainage or ground water.

PMID: 11599718 [PubMed - indexed for MEDLINE]


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