molinate
1H-azepine-1-carbothioic acid, hexahydro-, S-ethyl ester
 
Notes:
russian drug.
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CAS Number: 2212-67-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 218-661-0
FDA UNII: 68N5G08DJQ
Nikkaji Web: J1.802C
Beilstein Number: 1239196
MDL: MFCD00055352
XlogP3: 3.20 (est)
Molecular Weight: 187.30569000
Formula: C9 H17 N O S
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: herbicides / pesticides
 
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Physical Properties:
Appearance: colorless to pale yellow clear liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Boiling Point: 279.02 °C. @ 760.00 mm Hg (est)
Vapor Pressure: 0.005600 mmHg @ 25.00 °C. (est)
Flash Point: 253.00 °F. TCC ( 122.50 °C. ) (est)
logP (o/w): 3.210
Soluble in:
 water, 91.97 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Sigma-Aldrich
For experimental / research use only.
Molinate PESTANAL®, analytical standard
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
unreported-mammal (species unspecified) LD50  720 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(5), Pg. 29, 1980.

oral-mouse LD50  530 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SENSE ORGANS AND SPECIAL SENSES: CHANGES IN EXTRA-OCULAR MUSCLES: EYE
Vrachebnoe Delo. Medical Practice. Vol. (1), Pg. 119, 1969.

unreported-mouse LD50  545 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(10), Pg. 104, 1975.

oral-rat LD50  369 mg/kg
Pesticide Manual. Vol. 9, Pg. 594, 1991.

unreported-rat LD50  657 mg/kg
LUNGS, THORAX, OR RESPIRATION: DYSPNEA SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 40(10), Pg. 104, 1975.

Dermal Toxicity:
skin-rabbit LD50 3536 mg/kg
Farm Chemicals Handbook. Vol. -, Pg. C208, 1991.

skin-rat LD50 1167 mg/kg
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 35(8), Pg. 35, 1970.

Inhalation Toxicity:
inhalation-cat LC50 > 200 mg/m3
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 35(8), Pg. 35, 1970.

inhalation-rat LC50 2100 mg/m3/1H
"Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A282, Pg. 1983

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Safety in Use Information:
Category: herbicides / pesticides
Recommendation for molinate usage levels up to:
 not for fragrance use.
 
Recommendation for molinate flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Reasoned opinion on the review of the existing maximum residue levels (MRLs) for molinate according to Article 12 of Regulation (EC) No 396/2005
View page or View pdf
EPI System: View
EPA-Iris: IRIS
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 16653
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 S-ethyl azepane-1-carbothioate
Chemidplus: 0002212671
EPA/NOAA CAMEO: hazardous materials
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References:
 S-ethyl azepane-1-carbothioate
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 16653
Pubchem (sid): 134982850
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C11086
HMDB (The Human Metabolome Database): Search
ChemSpider: View
Wikipedia: View
Formulations/Preparations:
•usepaopp pesticide code 041402; trade names: hydram; ordram; r-4572; felan; jalan; yulan; and sakkimol. •ordram 63 (6 lbgal); ordram 5g (5% by wt). granules--5% & 10% active ingredient. •tech. material is 95% pure. •formulations of this product include an emulsifiable liquid (8 lb active ingredientgal and granules (10% active ingredient). •emulsifiable liquid, granules
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
1H-azepine-1-carbothioic acid hexahydro-S-ethyl ester
1H-azepine-1-carbothioic acid, hexahydro-, S-ethyl ester
S-ethyl 1-azepanecarbothioate
S-ethyl 1-hexamethyleneiminothiocarbamate
S-ethyl azepane-1-carbothioate
S-ethyl hexahydro-1H-azepine-1-carbothioate
S-ethyl hexahydroazepine-1-carbothioate
S-ethyl N,N-hexamethylenethiocarbamate
S-ethyl perhydroazepin-1-carbothioate
S-ethyl perhydroazepine-1-thiocarboxylate
S-ethyl-1-azepancarbothioat
S-ethyl-N-hexamethylenethiocarbamate
S-ethyl-N,N-hexamethylenethiocarbamate
S-ethylazepan-1-carbothioat
 felan
 higalnate
 hydram
 jalan
 molinex
 molmate
 ordram
 stauffer R 4572
 yalan
 yulan
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Articles:
PubMed: Shiga-Like Toxin B Subunit of Escherichia coli as Scaffold for High-Avidity Display of Anti-immunocomplex Peptides.
PubMed: Community air monitoring for pesticides-part 2: multiresidue determination of pesticides in air by gas chromatography, gas chromatography-mass spectrometry, and liquid chromatography-mass spectrometry.
PubMed: Community air monitoring for pesticides. Part 3: using health-based screening levels to evaluate results collected for a year.
PubMed: Four-year advanced monitoring program of polar pesticides in groundwater of Catalonia (NE-Spain).
PubMed: Microbial degradation of the herbicide molinate by defined cultures and in the environment.
PubMed: Dopaminergic neurotoxicity of S-ethyl N,N-dipropylthiocarbamate (EPTC), molinate, and S-methyl-N,N-diethylthiocarbamate (MeDETC) in Caenorhabditis elegans.
PubMed: Assessment of pesticide residues in Karaboğaz Lake from Kızılırmak Delta, Turkey.
PubMed: Molinate quantification in environmental water by a glutathione-S-transferase based biosensor.
PubMed: Nanopeptamers for the development of small-analyte lateral flow tests with a positive readout.
PubMed: Molinate biodegradation in soils: natural attenuation versus bioaugmentation.
PubMed: Determination of vitamin A and its metabolites in rat testis: possible involvement of vitamin A in testicular toxicity caused by molinate.
PubMed: Ultra-sensitive electrochemical immunosensor using analyte peptidomimetics selected from phage display peptide libraries.
PubMed: Gulosibacter molinativorax ON4T molinate hydrolase, a novel cobalt-dependent amidohydrolase.
PubMed: Changes of concentrations, shipment amounts and ecological risk of pesticides in river water flowing into Lake Biwa.
PubMed: Exposure of the cyanobacterium Nostoc muscorum from Portuguese rice fields to Molinate (Ordram(®)): Effects on the antioxidant system and fatty acid profile.
PubMed: Adsorption and desorption variability of four herbicides used in paddy rice production.
PubMed: Noncompetitive phage anti-immunocomplex real-time polymerase chain reaction for sensitive detection of small molecules.
PubMed: Relative inhibitory potency of molinate and metabolites with aldehyde dehydrogenase 2: implications for the mechanism of enzyme inhibition.
PubMed: Bacterial diversity and bioaugmentation in floodwater of a paddy field in the presence of the herbicide molinate.
PubMed: Accumulation of current-use and organochlorine pesticides in crab embryos from northern California, USA.
PubMed: Solid-phase extraction and gas chromatography-tandem mass spectrometry method for the simultaneous determination of several pesticides in water.
PubMed: A multi-residue method for pesticide residue analysis in rice grains using matrix solid-phase dispersion extraction and high-performance liquid chromatography-diode array detection.
PubMed: Cryopreserved hepatocytes from rainbow trout (Oncorhynchus mykiss): a validation study to support their application in bioaccumulation assessment.
PubMed: Development of PBPK model of molinate and molinate sulfoxide in rats and humans.
PubMed: Comparative toxicity of bentazon and molinate on growth, photosynthetic pigments, photosynthesis, and respiration of the Portuguese ricefield cyanobacterium Nostoc muscorum.
PubMed: Effects of thiobencarb in combinations with molinate and chlorpyrifos on selected soil microbial processes.
PubMed: Pesticides in water and sediment from littoral area of Lake Biwa.
PubMed: Pesticides in water, fish and shellfish from littoral area of Lake Biwa.
PubMed: [Emergent treatment of source water contaminated by representative herbicide molinate and ametryn].
PubMed: Effects of molinate on survival and development of Bombina orientalis (Boulenger) embryos.
PubMed: HPLC based method using sample precolumn cleanup for the determination of triazines and thiolcarbamates in hemodialysis saline solutions.
PubMed: Spatial and temporal distribution of pesticide residues in surface waters in northeastern Greece.
PubMed: Detoxification of molinate sulfoxide: comparison of spontaneous and enzmatic glutathione conjugation using human and rat liver cytosol.
PubMed: Xenobiotic intrinsic clearance in freshly isolated hepatocytes from rainbow trout (Oncorhynchus mykiss): determination of trout hepatocellularity, optimization of cell concentrations and comparison of serum and serum-free incubations.
PubMed: New insights into a bacterial metabolic and detoxifying association responsible for the mineralization of the thiocarbamate herbicide molinate.
PubMed: Analysis of 17 polar to semi-polar pesticides in the Ebro river delta during the main growing season of rice by automated on-line solid-phase extraction-liquid chromatography-tandem mass spectrometry.
PubMed: Assessing the biological relevance of exposing freshwater organisms to atrazine and molinate in environmentally realistic exposure test systems.
PubMed: Calibration and field application of a solvent-based cellulose membrane passive sampling device for the monitoring of polar herbicides.
PubMed: Pesticides removal in the process of drinking water production.
PubMed: Calibration and validation of a dynamic water model in agricultural scenarios.
PubMed: Determination of herbicides by solid phase extraction gas chromatography-mass spectrometry in drinking waters.
PubMed: Reactions of thiocarbamate, triazine and urea herbicides, RDX and benzenes on EPA Contaminant Candidate List with ozone and with hydroxyl radicals.
PubMed: Combined use of biomarkers and in situ bioassays in Daphnia magna to monitor environmental hazards of pesticides in the field.
PubMed: Acute toxicities of trace metals and common xenobiotics to the marine copepod Tigriopus japonicus: Evaluation of its use as a benchmark species for routine ecotoxicity tests in Western Pacific coastal regions.
PubMed: Determination of xenobiotic intrinsic clearance in freshly isolated hepatocytes from rainbow trout (Oncorhynchus mykiss) and rat and its application in bioaccumulation assessment.
PubMed: The use of Chironomus riparius larvae to assess effects of pesticides from rice fields in adjacent freshwater ecosystems.
PubMed: Field dissipation and environmental hazard assessment of clomazone, molinate, and thiobencarb in Australian rice culture.
PubMed: The influence of activated carbon surface properties on the adsorption of the herbicide molinate and the bio-regeneration of the adsorbent.
PubMed: Relative rate constants of contaminant candidate list pesticides with hydroxyl radicals.
PubMed: Organic contaminant loads into the Western Mediterranean Sea: estimate of Ebro River inputs.
PubMed: Study of the presence of pesticides in surface waters in the Ebro river basin (Spain).
PubMed: Mode of action: reduction of testosterone availability--molinate-induced inhibition of spermatogenesis.
PubMed: Environmental fate of the herbicide molinate in a rice-paddy-soil lysimeter.
PubMed: Effect of operating parameters on molinate biodegradation.
PubMed: Fully automated multianalyte determination of different classes of pesticides, at picogram per litre levels in water, by on-line solid-phase extraction-liquid chromatography-electrospray-tandem mass spectrometry.
PubMed: Effect of river water, sediment and time on the toxicity and bioavailability of molinate to the marine bacterium Vibrio fischeri (Microtox).
PubMed: Analyte peptidomimetics selected from phage display peptide libraries: a systematic strategy for the development of environmental immunoassays.
PubMed: Toxicity and bioavailability of atrazine and molinate to the freshwater fish (Melanotenia fluviatilis) under laboratory and simulated field conditions.
PubMed: A case study of molinate application in a Portuguese rice field: herbicide dissipation and proposal of a clean-up methodology.
PubMed: The toxicity and bioavailability of atrazine and molinate to Chironomus tepperi larvae in laboratory and river water in the presence and absence of sediment.
PubMed: Square-wave voltametric method for determination of molinate concentration in a biological process using a hanging mercury drop electrode.
PubMed: Acute exposure to molinate alters neuroendocrine control of ovulation in the rat.
PubMed: Toxicity and bioavailability of atrazine and molinate to the freshwater shrimp (Paratya australiensis) under laboratory and simulated field conditions.
PubMed: Laboratory investigation into the development of resistance of Daphnia magna to the herbicide molinate.
PubMed: Preliminary feasibility study for the use of an adsorption/bio-regeneration system for molinate removal from effluents.
PubMed: Toxicity of atrazine and molinate to the cladoceran Daphnia carinata and the effect of river water and bottom sediment on their bioavailability.
PubMed: Alternative control of two biotypes of Echinochloa phyllopogon susceptible and resistant to fenoxaprop-ethyl.
PubMed: Gulosibacter molinativorax gen. nov., sp. nov., a molinate-degrading bacterium, and classification of 'Brevibacterium helvolum' DSM 20419 as Pseudoclavibacter helvolus gen. nov., sp. nov.
PubMed: Oxidative degradation of the carbothioate herbicide, molinate, using nanoscale zero-valent iron.
PubMed: Characterization of S-(N,N-Dialkylaminocarbonyl)cysteine Adducts and Enzyme Inhibition Produced by Thiocarbamate Herbicides in the Rat.
PubMed: Robust and sensitive monoclonal enzyme-linked immunosorbent assay for the herbicide molinate.
PubMed: Cross-resistance pattern and alternative herbicides for Cyperus difformis resistant to sulfonylurea herbicides in Korea.
PubMed: Evaluation of the genotoxicity of four herbicides in the wing spot test of Drosophila melanogaster using two different strains.
PubMed: Multianalyte determination of different classes of pesticides (acidic, triazines, phenyl ureas, anilines, organophosphates, molinate and propanil) by liquid chromatography-electrospray-tandem mass spectrometry.
PubMed: A novel pathway for mineralization of the thiocarbamate herbicide molinate by a defined bacterial mixed culture.
PubMed: Sulfonylurea herbicide-resistant Monochoria vaginalis in Korean rice culture.
PubMed: Comparative study of the toxicity of molinate for freshwater organisms.
PubMed: Pesticides in Portuguese surface and ground waters.
PubMed: Community exposures to airborne agricultural pesticides in California: ranking of inhalation risks.
PubMed: Effects of bensulfuron-methyl and cinosulfuron on growth of four freshwater species of phytoplankton.
PubMed: Factors affecting multiresidue determination of priority herbicides when using solid-phase microextraction.
PubMed: Algal growth inhibition by river water pollutants in the agricultural area around Lake Biwa, Japan.
PubMed: Identification of a S-hexahydro-1H-azepine-1-carbonyl adduct produced by molinate on rat hemoglobin beta(2) and beta(3) chains in vivo.
PubMed: Application of the Microtox test and pollution indices to the study of water toxicity in the Albufera Natural Park (Valencia, Spain).
PubMed: Concentration and loading of pesticide residues in Lake Biwa basin (Japan).
PubMed: Glutathione-dependent resistance of the European eel Anguilla anguilla to the herbicide molinate.
PubMed: Laboratory and field studies on the effect of molinate, clomazone, and thiobencarb on nontarget aquatic invertebrates.
PubMed: Effects of the organophosphorus insecticide fenitrothion on growth in five freshwater species of phytoplankton.
PubMed: Effects of S-ethyl hexahydro-1H-azepine-1-carbothioate (molinate) on di-n-butyl dichlorovinyl phosphate (DBDCVP) neuropathy.
PubMed: Photodegradation of selected herbicides in various natural waters and soils under environmental conditions.
PubMed: Accumulative characteristics of pesticide residues in organs of bivalves (Anodonta woodiana and Corbicula leana) under natural conditions.
PubMed: Adsorption-desorption studies of selected herbicides in soil-Fly ash mixtures.
PubMed: Determination of rice herbicides, their transformation products and clofibric acid using on-line solid-phase extraction followed by liquid chromatography with diode array and atmospheric pressure chemical ionization mass spectrometric detection.
PubMed: Use of solid-phase microextraction for the quantitative determination of herbicides in soil and water samples.
PubMed: Simultaneous determination of acidic and non-acidic pesticides in natural waters by liquid chromatography-mass spectrometry.
PubMed: Cholinesterase activity and hematological parameters as biomarkers of sublethal molinate exposure in Anguilla anguilla.
PubMed: In vitro fertilization after in vivo treatment of rats with three reproductive toxicants.
PubMed: Comparison of the performance of graphitized carbon black and poly(styrene-divinylbenzene) cartridges for the determination of pesticides and industrial phosphates in environmental waters.
PubMed: An assessment of fertility in male workers exposed to molinate.
PubMed: Comparison of human and rat metabolism of molinate in liver microsomes and slices.
PubMed: In vivo and in vitro promutagen activation by Vicia faba of thiocarbamate herbicides molinate and butylate to products inducing sister chromatid exchanges in human lymphocyte cultures.
PubMed: The impact of rice pesticides on the aquatic ecosystems of the Sacramento River and Delta (California).
PubMed: Use of new microbiotests with Daphnia magna and Selenastrum capricornutum immobilized forms.
PubMed: Monitoring of pesticide residues and their metabolites in surface and underground waters of Imathia (N. Greece) by means of solid-phase extraction disks and gas chromatography.
PubMed: Effects of molinate on growth of five freshwater species of phytoplankton.
PubMed: On-line coupling of solid-phase extraction to gas chromatography with mass spectrometric detection to determine pesticides in water.
PubMed: The reproductive toxicity of molinate and metabolites to the male rat: effects on testosterone and sperm morphology.
PubMed: Molinate: rodent reproductive toxicity and its relevance to humans--a review.
PubMed: Identification of a carboxylesterase as the major protein bound by molinate.
PubMed: Testicular toxicity of molinate in the rat: metabolic activation via sulfoxidation.
PubMed: Pesticides and their oxidation products in water and fish from rivers flowing into Lake Biwa.
PubMed: Effects of the herbicide molinate on mixotrophic growth, photosynthetic pigments, and protein content of Anabaena sphaerica under different light conditions.
PubMed: Physiological responses of fathead minnow larvae to rice pesticides.
PubMed: Genotoxicity of six pesticides by Salmonella mutagenicity test and SOS chromotest.
PubMed: Characterization of risks associated with the use of molinate.
PubMed: [Gas chromatographic analysis of molinate residue in rice].
PubMed: Environmental fate of rice pesticides in California.
PubMed: S-methylation as a bioactivation mechanism for mono- and dithiocarbamate pesticides as aldehyde dehydrogenase inhibitors.
PubMed: Acute and chronic toxicity of the thiocarbamate herbicide, molinate, to the cladoceran Moina australiensis Sars.
PubMed: Evaluation of herbicide migration from water to gorgonzola and mozzarella cheeses in industrial processing.
PubMed: Inhibition of rat liver low Km aldehyde dehydrogenase by thiocarbamate herbicides. Occupational implications.
PubMed: Aldehyde dehydrogenase of mice inhibited by thiocarbamate herbicides.
PubMed: Sublethal effects of three pesticides on Japanese medaka.
PubMed: Biological monitoring for pesticide absorption.
PubMed: Biological monitoring for pesticide exposure--the role of human volunteer studies.
PubMed: Reproductive risks from contaminants in drinking water.
PubMed: Molinate decontamination processes in effluent water from rice fields.
PubMed: Mitotic toxicity, sister chromatid exchange, and rec assay of pesticides.
PubMed: Lethality, hexobarbital narcosis and behavior in rats exposed to atrazine, bentazon or molinate.
PubMed: The effect of structurally divergent herbicides on mouse liver xenobiotic-metabolizing enzymes (P-450-dependent mono-oxygenases, epoxide hydrolases and glutathione S-transferases) and carnitine acetyltransferase.
PubMed: Cytogenetic effect of the thiocarbamate herbicides butylate, molinate and vernolate in the mouse bone marrow micronucleus test.
PubMed: Comparison of an enzyme-linked immunosorbent assay and a gas chromatographic procedure for the determination of molinate residues.
PubMed: Genotoxicity of selected herbicides.
PubMed: WHO drinking water quality guidelines for selected herbicides.
PubMed: Comparative biotransformation of molinate (Ordram) in the white sturgeon (Acipenser transmontanus) and common carp (Cyprinus carpio).
PubMed: Pesticide residues in Lake Albufera, Valencia, Spain.
PubMed: Toxicity of some ricefield pesticides to the crayfish P. clarkii, under laboratory and field conditions in Lake Albufera (Spain).
PubMed: Evaluation of immune function in mice exposed to Ordram.
PubMed: The effects of selected rice and soybean pesticides on the eggs of Psorophora columbiae.
PubMed: Worker exposure during aerial application of a liquid and a granular formulation of Ordram Selective Herbicide to rice.
PubMed: [New products of the microbial degradation of ordram].
PubMed: [Ordram transformation by microorganisms].
PubMed: [Role of coryneform bacteria in the degradation of ordram in a reservoir].
PubMed: The degradation of [14C]molinate in soil under flooded and nonflooded conditions.
PubMed: Herbicidal treatments for control of Papaver somniferum L.
PubMed: Mercapturic acid occurrence in fish bile. A terminal product of metabolism of the herbicide molinate.
PubMed: Metabolism of [ring-14C]ordram (molinate) in the rat. 2. Urinary metabolite identification.
PubMed: Metabolism of [ring-14C]ordram (molinate) in the rat. I. Balance and tissue residue study.
PubMed: Acute toxicity of the insecticides toxaphene and carbaryl and the herbicides propanil and molinate to four species of aquatic organisms.
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