thiophanate-methyl
allophanic acid, 4,4'-o-phenylenebis(3-thio-, dimethyl ester
Identification
| Name | thiophanate-methyl |
| IUPAC | methyl N-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate |
| CAS Number | 23564-05-8 |
| EINECS | 245-740-7 |
| FDA UNII | K4N81R84L8 |
| Molecular Formula | C12 H14 N4 O4 S2 |
| Molecular Weight | 342.39838000 |
| MDL Number | MFCD00055294 |
| Nikkaji Number | J3.471A |
| Beilstein | 0937942 |
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 Toxicity | oral-dog LDLo 4000 mg/kg |
| Dermal Toxicity | skin-guinea pig LD50 > 10000 mg/kg |
| Inhalation Toxicity | inhalation-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
| Category | herbicides / pesticides |
| Recommendation for thiophanate-methyl usage levels up to | not for fragrance use. |
| Recommendation for thiophanate-methyl flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
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.