thiophanate-methyl

allophanic acid, 4,4'-o-phenylenebis(3-thio-, dimethyl ester

CAS: 23564-05-8 C12 H14 N4 O4 S2 MW: 342.39838000

Identification

Namethiophanate-methyl
IUPACmethyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate
CAS Number23564-05-8
EINECS245-740-7
FDA UNIIK4N81R84L8
Molecular FormulaC12 H14 N4 O4 S2
Molecular Weight342.39838000
MDL NumberMFCD00055294
Nikkaji NumberJ3.471A
Beilstein0937942

Regulatory

Physical Properties

Appearance light brown powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 172.00 °C. @ 760.00 mm Hg
Vapor Pressure 7.130000 mmHg @ 25.00 °C. (est)
Flash Point 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w) 1.400
Soluble in water, 26.6 mg/L @ 20 °C (exp)

No sensory data available

Safety Information

Oral/Parenteral Toxicityoral-dog LDLo 4000 mg/kg
Dermal Toxicityskin-guinea pig LD50 > 10000 mg/kg
Inhalation Toxicityinhalation-rat LC50 1700 mg/m3/4H

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryherbicides / pesticides
Recommendation for thiophanate-methyl usage levels up tonot for fragrance use.
Recommendation for thiophanate-methyl flavor usage levels up tonot for flavor use.

No supplier data available

Potential Uses

None Found

Natural Occurrence

not found in nature

Synonyms

allophanic acid, 4,4'-o-phenylenebis(3-thio-, dimethyl ester caligran carbamic acid, (1,2-phenylenebis(iminocarbonothioyl))bis-, dimethyl ester carbamic acid, (1,2-phenylenebis(iminocarbonothioyl)bis-, dimethyl ester cercobin M cercobin methyl 1,2- di-(3-methoxycarbonyl-2-thioureido)benzene dimethyl ((1,2-phenylene)bis-(iminocarbonothioyl))bis(carbamate) dimethyl ((1,2-phenylene)bis(iminocarbonothioyl))bis(carbamate) dimethyl 4,4'-o-phenylenebis(3-thioallophanate) ditek enovit M enovit methyl fungo fungo 50 o-bis(3- methoxycarbonyl-2-thioureido)benzene 1,2-bis(3-( methoxycarbonyl)-2-thioureido)benzene 1,2-bis( methoxycarbonylthioureido)benzene methyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate methyl thiophanate methyl topsin methylthiofanate methylthiophanate metoben mildothane neotopsin PELT 14 PELT-44 sipcaplant sipcasan sipcavit thiophanate M thiophanate methyl tiofanate metile topsin M topsin Methyl topsin NF 44 topsin NF-44 topsin WP methyl topsin-M PubMed: Isolation and Characterization of the Colletotrichum acutatum ABC Transporter CaABC1. PubMed: Sensitivity of Podosphaera xanthii populations to anti-powdery-mildew fungicides in Spain. PubMed: A variety of pesticides trigger in vitro α-synuclein accumulation, a key event in Parkinson's disease. PubMed: Independent Emergence of Resistance to Seven Chemical Classes of Fungicides in Botrytis cinerea. PubMed: Methyl-thiophanate increases reactive oxygen species production and induces genotoxicity in rat peripheral blood. PubMed: Multiresidue determination of 256 pesticides in lavandin essential oil by LC/ESI/sSRM: advantages and drawbacks of a sampling method involving evaporation under nitrogen. PubMed: Simultaneous determination of thiophanate-methyl and its metabolite carbendazim in tea using isotope dilution ultra performance liquid chromatography-tandem mass spectrometry. PubMed: Influence of different planting seasons of six leaf vegetables on residues of five pesticides. PubMed: Simultaneous quantification of alleles E198A and H6Y in the β-tubulin gene conferring benzimidazole resistance in Monilinia fructicola using a duplex real-time (TaqMan) PCR. PubMed: MSPD sample preparation approach for reversed-phase liquid chromatographic analysis of pesticide residues in stem of coconut palm. PubMed: Salting-out assisted liquid-liquid extraction with the aid of experimental design for determination of benzimidazole fungicides in high salinity samples by high-performance liquid chromatography. PubMed: Spinach or amaranth may represent highest residue of thiophanate-methyl with open field application on six leaf vegetables. PubMed: Effect of preharvest anti-fungal compounds on Aspergillus steynii and A. carbonarius under fluctuating and extreme environmental conditions. PubMed: Unlikely remedy: fungicide clears infection from pathogenic fungus in larval southern leopard frogs (Lithobates sphenocephalus). PubMed: Rational coformer or solvent selection for pharmaceutical cocrystallization or desolvation. PubMed: [Determination of thiophanate-methyl and carbendazim in cucumber and soil by QuEChERS-high performance liquid chromatography-triple quadrupole tandem mass spectrometry]. PubMed: [Rapid determination of 6 pesticide residues in tomato paste by ultra performance liquid chromatography-tandem mass spectrometry]. PubMed: Characterization of Paecilomycescinnamomeus from the camellia whitefly, Aleurocanthus camelliae (Hemiptera: Aleyrodidae), infesting tea in Japan. PubMed: Evaluation of fungicides for the management of Botryosphaeria dieback diseases of grapevines. PubMed: Investigating phenotypic variability in Colletotrichum lindemuthianum populations. PubMed: The impact of pesticides on the pathogen Batrachochytrium dendrobatidis independent of potential hosts. PubMed: The genetic profile and molecular diagnosis of thiophanate-methyl resistant strains of Fusarium asiaticum in Japan. PubMed: Testicular toxicity of methyl thiophanate in the Italian wall lizard (Podarcis sicula): morphological and molecular evaluation. PubMed: Determination of sixteen pesticides in peppers using high-performance liquid chromatography/mass spectrometry. PubMed: Determination of carbendazim, thiophanate, thiophanate-methyl and benomyl residues in agricultural products by liquid chromatography-tandem mass spectrometry. PubMed: Optical spectroscopy studies of the interaction between thiophanate methyl and human serum albumin for biosensor applications. PubMed: Genotoxic effects of the fungicide thiophanate-methyl on Podarcis sicula assessed by micronucleus test, comet assay and chromosome analysis. PubMed: Biodegradation kinetics of the benzimidazole fungicide thiophanate-methyl by bacteria isolated from loamy sand soil. PubMed: Potential for bioremediation of agro-industrial effluents with high loads of pesticides by selected fungi. PubMed: [Pathogen identification of Pinellia ternata tuber disease and selection of fungicide]. PubMed: Dissipation study of thiophanate methyl residue in/on grapes (Vitis vinifera L.) in India. PubMed: Genotoxic fungicide methyl thiophanate as an oxidative stressor inducing 8-oxo-7,8-dihydro-2' -deoxyguanosine adducts in DNA and mutagenesis. PubMed: Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-triazole) Mannich bases containing piperazine rings. PubMed: Methyl thiophanate as a DNA minor groove binder produces MT-Cu(II)-DNA ternary complex preferably with AT rich region for initiation of DNA damage. PubMed: Fungicide methyl thiophanate binding at sub-domain IIA of human serum albumin triggers conformational change and protein damage. PubMed: Pesticide extraction from table grapes and plums using ionic liquid based dispersive liquid-liquid microextraction. PubMed: Description of Cryptosporiopsis kienholzii and species profiles of Neofabraea in major pome fruit growing districts in the Pacific Northwest USA. PubMed: Ionic liquid based dispersive liquid-liquid microextraction for the extraction of pesticides from bananas. PubMed: Flower-inhabiting Frankliniella Thrips (Thysanoptera: Thripidae), pesticides, and Fusarium hardlock in cotton. PubMed: Determination of multi-class pesticides in wines by solid-phase extraction and liquid chromatography-tandem mass spectrometry. PubMed: Assessment of methyl thiophanate-Cu (II) induced DNA damage in human lymphocytes. PubMed: In vitro toxicity of selected fungicides from the groups of benzimidazoles and demethylation inhibitors to Cladobotryum dendroides and Agaricus bisporus. PubMed: In vitro study on the interaction between thiophanate methyl and human serum albumin. PubMed: Rapid development of fungicide resistance by Sclerotinia homoeocarpa on turfgrass. PubMed: Genetic Analysis of Isolates of Botrytis cinerea Sensitive and Resistant to Benzimidazole and Dicarboximide Fungicides. PubMed: Combinations of Fungicides with Phylloplane Yeasts for Improved Control of Botrytis cinerea on Geranium Seedlings. PubMed: Adaptation to fungicides in Monilinia fructicola isolates with different fungicide resistance phenotypes. PubMed: Screening preharvest/postharvest strategies to prevent fruit rot decay. PubMed: [Study on usage of pesticides in various countries]. PubMed: Morphological and functional changes in the thyroid gland of methyl thiophanate-injected lizards, Podarcis sicula. PubMed: Molecular characterization of benzimidazole-resistant isolates of Cladosporium fulvum. PubMed: Quantification of allele E198A in beta-tubulin conferring benzimidazole resistance in Monilinia fructicola using real-time PCR. PubMed: Application of genetic algorithm for selection of variables for the BLLS method applied to determination of pesticides and metabolites in wine. PubMed: The effects of the fungicide methyl thiophanate on adrenal gland morphophysiology of the lizard, Podarcis sicula. PubMed: Determination of thiophanate methyl and carbendazim residues in vegetable samples using microwave-assisted extraction. PubMed: [Susceptibility of Trichogramma pretiosum Riley (Hymenoptera: Trichogrammatidae) adults to fungicides used to control apple diseases]. PubMed: PPARalpha mediates the effects of the pesticide methyl thiophanate on liver of the lizard Podarcis sicula. PubMed: Impact of the stem borer, Dectes texanus, on yield of the cultivated sunflower, Helianthus annuus. PubMed: Survival of adult Tiphia vernalis (Hymenoptera: Tiphiidae) after insecticide, fungicide, and herbicide exposure in laboratory bioassays. PubMed: The newt Triturus carnifex as a model for monitoring the ecotoxic impact of the fungicide thiophanate methyl: adverse effects on the adrenal gland. PubMed: [Determination of thiophanate-methyl residue in peppers by solid phase extraction-HPLC]. PubMed: Characterization and PCR-based detection of benzimidazole-resistant isolates of Monilinia laxa in California. PubMed: Effects of thiophanate-methyl and glyphosate on asexual and sexual reproduction in the rotifer Brachionus calyciflorus Pallas. PubMed: A simple and rapid spectrophotometric method for determination of thiophanate-methyl in commercial formulations and its residues in foodstuffs. PubMed: Activity of some chemicals in the control of Botrytis cinerea on roses. PubMed: Re-identification and characterization of pathogens causing ugurassa (Flacourtia inermis) fruit anthracnose. PubMed: Effect of thiophanate-methyl on the reproduction and survival of the freshwater rotifer Brachionus calyciflorus Pallas. PubMed: Identification and characterization of benzimidazole resistance in Monilinia fructicola from stone fruit orchards in California. PubMed: Histological and histomorphometric alterations in thyroid and adrenals of CD rat pups exposed in utero to methyl thiophanate. PubMed: Complexation of several fungicides with beta-cyclodextrin: determination of the association constants and isolation of the solid complexes. PubMed: Risk assessment of pesticide runoff from turf. PubMed: [Effects of Atractylodes macrocephala seeds coated with SCF on field diseases]. PubMed: On-line automated sample preparation for liquid chromatography using parallel supported liquid membrane extraction and microporous membrane liquid-liquid extraction. PubMed: Effect of insecticides and fungicides on the interaction between members of the mite families Phytoseiidae and Stigmaeidae on citrus. PubMed: [Effect of pesticides on field-controlling root rot of Vicia faba]. PubMed: Differential sensitivity of two green algae, Scenedesmus obliqnus and Chlorella pyrenoidosa, to 12 pesticides. PubMed: [Renal dysfunction in chemical plant workers producing dust pesticides]. PubMed: Liquid chromatographic-mass spectrometric determination of post-harvest fungicides in citrus fruits. PubMed: Determination of thiophanate-methyl and its metabolites at trace level in spiked natural water using the supported liquid membrane extraction and the microporous membrane liquid-liquid extraction techniques combined on-line with high-performance liquid chromatography. PubMed: Determination of imidacloprid and benzimidazole residues in fruits and vegetables by liquid chromatography-mass spectrometry after ethyl acetate multiresidue extraction. PubMed: Flow cytometric analysis of genetic damage, effect on cell cycle progression, and apoptosis by thiophanate-methyl in human lymphocytes. PubMed: Molecular non-genetic biomarkers of effect related to methyl thiophanate cocarcinogenesis: organ- and sex-specific cytochrome P450 induction in the rat. PubMed: Analysis of carbendazim, benomyl, thiophanate methyl and 2,4-dichlorophenoxyacetic acid in fruits and vegetables after supercritical fluid extraction. PubMed: In vivo studies on possible adverse effects on reproduction of the fungicide methyl thiophanate. PubMed: Effects of Some Pesticides on the Growth of ARF18 and Its Pathogenicity to Heterodera glycines. PubMed: Cytotoxic and cell transforming activities of the fungicide methyl thiophanate on BALB/c 3T3 cells in vitro. PubMed: Cytogenetic effects of benzimidazoles in mouse bone marrow. PubMed: Pesticides in the cultivation of carnations in greenhouses: Part I--Exposure and concomitant health risk. PubMed: Postharvest-applied agrochemicals and their residues in fresh fruits and vegetables. PubMed: Ion-pairing liquid chromatographic determination of benzimidazole fungicides in foods. PubMed: An oxidimetric method for the determination of thiophanatemethyl in commercial formulations. PubMed: Determination of thiophanate methyl as carbendazin by high-pressure liquid chromatography: application to onions and cabbage. PubMed: Cytogenetic hazards from agricultural chemicals. 4. Sequential screening in the barley progeny test for cytogenetic activity of some systemic fungicides and a metabolite. PubMed: [Use of fungi as a biological test for determination of fungicide residues in plant material. II. Determination of benomyl, dichlofluanide, folpet, captane, carbendazyme, methyl thiophanate and thiram in fruit, vegetables and champignons]. PubMed: [Use of fungi as a biological test for the determination of residues of various fungicides in plant material. I. Determination of benomyl, methyl thiophanate, carbendazyme and thiabendazol in lemons, oranges, grapefruit and bananas]. PubMed: The toxicity of benomyl, thiophanate-methyl, and BCM to four freshwater organisms. PubMed: Effect of benomyl and thiophanate-methyl on metabolic activities of Rhizoctonia solani Kühn. PubMed: Persistence and metabolism of thiophanate-methyl in soil. PubMed: Mutagenic, cytogenetic and teratogenic studies on thiophanate-methyl. PubMed: Some pharmacologic properties of a new fungicide thiophanate-methyl. PubMed: Acute toxicity on dimethyl 4,4'-o-phenylene bis(3-thioallophanate), thiophanate-methyl fungicide.