23564-05-8 Usage
Description
Thiophanate-methyl, a member of the benzimidazole class, is a systemic fungicide with protective and curative activity against a broad spectrum of fungal diseases. It exists as colorless crystals or a light brown powder and is effective in controlling various plant diseases in stone fruit, pome fruit, tropical and subtropical fruit crops, grapes, and fruiting vegetables.
Used in Agriculture:
Thiophanate-methyl is used as a fungicide and wound protectant for controlling plant diseases in a variety of crops. It is effective against fungal diseases such as leaf spots, blotches, blights, fruit spots and rots, sooty mould, scabs, bulb/corn/tuber decays, blossom blights, powdery mildews, certain rusts, and common soil-borne crown and root rots.
Used in Fruit Crops:
Thiophanate-methyl is used as a fungicide to protect against powdery mildew, rot, and other fungal diseases in fruits, including stone fruit, pome fruit, tropical, and subtropical fruit crops.
Used in Vegetable Crops:
Thiophanate-methyl is used as a fungicide to control a broad spectrum of fungal diseases in vegetables, such as leaf spots, blotches, blights, and powdery mildews.
Used in Turf and Ornamentals:
Thiophanate-methyl is used as a fungicide to control fungal diseases in turf and ornamental plants, including shade trees, in fields, nurseries, and greenhouses.
Used in Systemic Fungicide:
Thiophanate-methyl is used as a systemic fungicide, providing protection and curative action against a wide range of fungal diseases in various crops, including fruits, vegetables, turf, and ornamentals.
Chemical Properties:
Thiophanate-methyl is characterized by its colorless crystals, prisms, or light brown powder appearance. It has low mammalian toxicity but is an irritant and a skin sensitizer. It may also be mutagenic, with moderate toxicity observed for aquatic organisms and earthworms.
Registration and Use:
In the European Union, thiophanate-methyl is approved for controlling fungal diseases on crops. In Australia, it is not registered for use on food-producing species but is used for the control of soil-borne diseases in ornamental plants. In the United States, it is registered for use in controlling a broad spectrum of fungal diseases on fruits, vegetables, turf, and ornamentals.
Formulation:
For application, thiophanate-methyl is formulated into wettable powders containing 50% and 70% active ingredients.
References
https://apvma.gov.au
https://www.epa.gov
https://sitem.herts.ac.uk
http://www.inchem.org
Terry R Roberts, David H Hutson, Philip W Lee, Peter H Nicholls, and Jack R Plimmer, Metabolic Pathways of Agrochemicals: Part 2: Insecticides and Fungicides, 1999, ISBN 978-0-85404-499-3
Air & Water Reactions
Insoluble in water.
Reactivity Profile
Thiophanate-methyl is incompatible with strong acids and bases, and with strong reducing agents such as hydrides. Produces flammable gaseous hydrogen with active metals or nitrides. Incompatible with strong oxidizing acids, peroxides. Incompatible with alkaline material. Forms complexes with copper salts .
Fire Hazard
Flash point data for Thiophanate-methyl are not available. Thiophanate-methyl is probably combustible.
Flammability and Explosibility
Notclassified
Trade name
BASF? 32500 F; BASF? 32500 Fungicide;
CERCOBIN?; CLEARY? 3336; CONSYST?;
DITEK?[C]; DOMAIN?; DOUSAN?[C]; ENOVIT?;
EVOLVE?; FANATE?; FUNGITOX?; FUNGO?;
MILDOTHANE? Turf Liquid; NEOTOPSIN?; NF-
35?; NF-44?; NSC 170810?; PELT?; PRO-TURF?;
SIPCAVIT?; SNARE?; SPECTRO?; SYSTEC?;
SYSTEMIC? FUNGICIDE; TD 1771?; TOPSIN?;
TOPSIN-WP METHYL?; 3336 TURF FUNGICIDE?;
ZYBAN?
Potential Exposure
Methyl thiophanate is thiocarbamate ester, used in the synthesis of polymers and in agriculture as pesticides, soil fumigants, and seed disinfectants.
Carcinogenicity
Those long-term studies evaluated a
variety of toxicity end points including carcinogenicity.
Both benomyl and carbendazim were weak carcinogens in
some in vivo studies. Rats of the SpDxAug strain were fed 80,
400, and 2000 ppm for 2 years and no evidence for an
increase in tumors was seen. In carcinogenicity
studies in mice with carbendazim, similar liver tumor finding
were found in CD-1 or Swiss strains. On the other
hand, no evidence of tumors was seen in a similar study
conducted using the NMRKf mouse strain, a strain that has a
low incidence of spontaneous tumors.
Metabolic pathway
Thiophanate methyl degradation in water (hydrolytic/ photolysis), soils,
plants and animals follows a common pathway that involves the initial
conversion into methyl benzimidazol-2-ylcarbamate (carbendazim).
Prior to benzimidazole ring formation, at least one side chain undergoes
an oxidative desulfuration reaction and partial hydrolysis (even to
the substituted aniline). Once formed, carbendazim is degraded primarily
via an oxidative mechanism (in animals) or through hydrolysis
to 2-aminobenzimidazole (in soils). Possible metabolism pathways of
thiophanate methyl are depicted in Scheme 1.
Shipping
UN2771 Thiocarbamate pesticides, solid, toxic, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Degradation
Thiophanate methyl (1) is susceptible to alkaline hydrolysis. The principal
degradation product is carbendazim (2). Thiophanate methyl degraded
slowly in water (pH 7-7.4, Noguchi et al., 1971), and in fruit juice (grape
homogenate, Shiga et al., 1985) to primarily carbendazim, but also to 1-(3-
methoxycarbony1thioureido)-2-(3-methoxycarbony1ureido)benzene (3)
and dimethyl 4,4'-(o-phenylene)bis(allophanate) (4).
Thiophanate methyl underwent photolysis in aqueous solution to
carbendazim (DT50 <1 day) when illuminated with UV light (254 nm)
or natural sunlight. A similar photolytic transformation occurred on
moist cotton foliage, although no photolysis occurred when thiophanate
methyl was exposed as a dry film to light (Buchenauer et al., 1973).
Thiophanate methyl on wet filter paper decomposed in sunlight to yield
carbendazim and small amounts of compounds 3 and 4 (Ono and
Tohyama, 1982).
Incompatibilities
Thiocarbamate esters are combustible; dust may form explosive mixture with air. Decomposes163℃Thiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Poisonous gases are generated by the thermal decomposition of thiocarbamate compounds, including carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, and methylamine. Thio and dithio carbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids. Flammable gases are generated by the combination of thiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates are incompatible with acids, peroxides, and acid halides.
Waste Disposal
In accordance with 40CFR 165 recommendations for the disposal of pesticides and pesticide containers. Must be disposed properly by following package label directions or by contacting your local or federal environmental control agency, or by contacting your regional EPA office. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
Check Digit Verification of cas no
The CAS Registry Mumber 23564-05-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,5,6 and 4 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 23564-05:
(7*2)+(6*3)+(5*5)+(4*6)+(3*4)+(2*0)+(1*5)=98
98 % 10 = 8
So 23564-05-8 is a valid CAS Registry Number.
InChI:InChI=1/C12H14N4O4S2/c1-19-11(17)15(9(13)21)7-5-3-4-6-8(7)16(10(14)22)12(18)20-2/h3-6H,1-2H3,(H2,13,21)(H2,14,22)
23564-05-8Relevant articles and documents
Synthesis method of thiophanate-methyl
-
Paragraph 0028-0100, (2020/10/04)
The invention belongs to the technical field of pesticide synthesis, and particularly relates to a synthesis method of thiophanate-methyl. The synthetic method of thiophanate-methyl comprises the following steps: dropwise adding an acetone solution of methyl isothiocyanate into an acetone-acetonitrile solution of o-phenylenediamine; carrying out insulation reaction, cooling crystallization to obtain thiophanate-methyl crystals, wherein a small amount of methyl isothiocyanate is contacted with a large amount of o-phenylenediamine, the contact area of methyl isothiocyanate and o-phenylenediamineis increased, the problem that molecular contact is uneven when o-phenylenediamine is dropwise added into methyl isothiocyanate conventionally is solved, the reaction process is more controllable, and the material rushing phenomenon does not exist. According to the method, acetone and acetonitrile are strong polar solvents, o-phenylenediamine is dissloved in an acetone-acetonitrile mixed solvent,and the volume ratio of acetone to acetonitrile is controlled to be 100: (11-15), so that the solubility of o-phenylenediamine is improved, the contact time of methyl isothiocyanate and o-phenylenediamine is prolonged, the reaction is more complete, and the productivity is improved.
Iminooxy-substituted benzyl phenyl ethers, processes and intermediates for their preparation, compositions comprising them, and their use for controlling harmful fungi
-
, (2008/06/13)
Iminooxy-substituted benzyl phenyl ethers of the formula I in which the substituents and the index are as defined below: Y is H, CH3, F or Cl; Q is C(═CHOCH3)—COOCH3, C(═CHCH3)—COOCH3, C(═NOCH3)—COOCH3, C(═NOCH3)—CONHCH3 or N(—OCH3)—COOCH3; X is hydrogen, halogen, alkyl, alkoxy or CF3; m is 1 or 2, where the radicals X may be different if m=2; R1 is alkyl and R2 is hydrogen or alkyl; or R1 and R2 together are cyclopropyl, cyclopentyl or cyclohexyl; R3 is alkyl or CF3; and R4 is alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; processes and intermediates for their preparation, compositions comprising them, and their use, are described.
Bisimino-substituted phenyl compounds and their use as pesticides
-
, (2008/06/13)
Imino-substituted phenyl compounds of the formula I where the substituents have the following meanings:z is a group A or B ?where? denotes the bond with the phenyl ring and?Ra is halogen, alkyl or alkoxy;y is halogen, alkyl, haloalkyl or alkoxy;n is 0, 1 or 2, it being possible for the radicals Y to be different if n=2;R1 is halogen, haloalkyl or alkoxy;R2 is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl;R3 is cyano, alkyl, haloalkyl, alkoxy, cycloalkoxy, alkoxyalkyl;?unsubstituted or substituted cycloalkyl, aryl, aryloxy or arylmethylene, heteroaryl, heterocyclyl,?C(R3a)=N—OR3b or C(R3a)=CR3cR3d, whereR3a, R3b, R3c, R3d independently of one another are hydrogen, alkyl or unsubstituted or substituted phenyl,processes for their preparation, and their use.
