759-94-4

Usage

Uses

Used in Agriculture:
EPTC is used as a preemergence herbicide for controlling perennial and annual grasses such as johnsongrass, nutgrass, and quackgrass. It is also effective against some broadleaved weeds, including chickweed, henbit, lambsquarters, pigweed, and purslane.
Used in Various Crops:
EPTC is utilized in the cultivation of vegetable crops, alfalfa, cotton, flax, pineapple, almonds, and walnuts, ensuring the growth of healthy crops by eliminating unwanted weeds and grasses.

Synthesis Reference(s)

Journal of the American Chemical Society, 81, p. 714, 1959 DOI: 10.1021/ja01512a052

Air & Water Reactions

Water insoluble. Slowly decomposes in water to form carbon disulfide and propyl amine. Such decompositions are accelerated by acids.

Reactivity Profile

Eradicane may generate flammable gases with aldehydes, nitrides, and hydrides. Incompatible with acids, peroxides, and acid halides.

Health Hazard

SYMPTOMS: Symptoms of exposure to Eradicane may include headache, giddiness, nervousness, blurred vision, weakness, nausea, cramps, diarrhea, sweating, miosis, tearing, salivation, vomiting and cyanosis.

Fire Hazard

Flash point data are not available for Eradicane, but Eradicane is probably combustible.

Flammability and Explosibility

Nonflammable

Trade name

ALIROX?; EPTAM?; EPTAM? 6E; EPTAM 2.3G (granular, 2.3% by weight); EPTAM 10G (granular, 10% by weight); ERADICANE?; GENEP? EPTC; R-1608?; SHORTSTOP?; STAUFFER? R 1608; TORBIN?

Safety Profile

Poison by ingestion, inhalation, and intravenous routes. Moderately toxic by skin contact route. Mutation data reported. An herbicide. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also CARBAMATES

Potential Exposure

EPTC is a pre-emergence and early postemergence thiocarbamate herbicide used to control the growth of germinating annual weeds, including broadleaves, grasses, and sedges. It is used in every region of the United States in the production of a wide variety of food crops. The heaviest usage is in the Corn Belt, Northeastern and Mid-Atlantic states, Coastal and Northern Great Plains and in the Pacific Northwest on corn, potatoes, sweet potatoes, dry beans, peas, alfalfa, and snap beans. EPTC is also used on home-grown vegetables and ornamentals. Some formulations are Restricted Group Pesticides (RUP)

Environmental Fate

Soil. EPTC is rapidly degraded by soil microbes and fungi yielding carbon dioxide, ethyl mercaptan and amino residues (Kaufman, 1967; Lee, 1984; Hartley and Kidd, 1987). Degradation occurs via hydrolysis of the ester linkage forming the corresponding mercaptan, alkylamine (n-dipropylamine) and carbon dioxide. Transthiolation and oxidation of the mercaptan forms the alcohol which is further oxidized to afford a metabolic pool (Kaufman, 1967). EPTC partially degraded in both sterile and nonsterile clay soils. Mineralization was not observed since carbon dioxide was not detected (MacRae and Alex- ander, 1965). EPTC sulfoxide was also reported as a metabolite identified in soil (Somasundaram and Coats, 1991) and in corn plants (Casida et al., 1974). The rapid formation of carbon dioxide was also observed from the microbial degradation of EPTC by a microbial metabolite isolated from Jimtown loam soil and designated JE1 (Dick et al., 1990). These researchers proposed that EPTC hydroxylated at the a-propyl carbon forming the unstable a-hydroxypropyl EPTC which degrades to N-depropyl EPTC and propionaldehyde. Metabolization of N-depropyl EPTC yields s-ethyl formic acid and propylamine. Demethylation of s-ethyl formic acid gives s-methyl formic acid. Propylamine and smethyl formic acid probably degrades to ammonia and methyl mercaptan, respectively and carbon dioxide (Dick et al., 1990). The reported half-lives in soil ranged from 2 to 4 weeks in two agricultural soils (Regina heavy clay and Weyburn loam) (Smith and Fitzpatrick, 1970) to 30 days (Jury et al., 1987). Rajagopal et al. (1989) reported that the persistence of EPTC in soil ranged from <4 to 6 weeks when applied at recommended rates. Plant. EPTC is rapidly metabolized by plants to carbon dioxide and naturally occurring plants constituents (Humburg et al., 1989). Chemical/Physical. Emits toxic fumes of phosphorus and sulfur oxides when heated to decomposition (Sax and Lewis, 1987). In the gas phase, EPTC reacts with hydroxyl and/or NO3 radicals but not with ozone. With hydroxy radicals in the presence of NO3, S-ethyl N-formyl-N-propylthiocarbamate formed as the major product. With NO3 radicals only, the major product was C3H7(CHO)NC(O)SC2H5. In addition, a minor product formed tentatively identified as CH3CH2CH2(CH3CH2C(O))NC(O)SCH2CH3. The calculated photolysis lifetimes of EPTC in the troposphere with hydroxyl and NO3 radicals are 5.8 hours and 5.0 days, respectively (Kwok et al., 1992).

Metabolic pathway

A new class of xenobiotic metabolite derived from the glutathione conjugate is produced by corn, cotton, and corn cell suspension cultures treated with 14C-EPTC (S-ethyl dipropylthiocarbamate). This metabolite is characterized as S-(N,N-dipropylcarbamoyl)-O- malonyl-3-thiolactic acid and is not detected in soybean plants or peanut cell suspension cultures. A second major metabolite of EPTC, S-(N,N- dipropylcarbamoyl)-N-malonylcysteine, is present in all tissues.

Shipping

UN2902 Pesticides, liquid, toxic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Incompatibilities

Thiocarbamate esters are combustible. They react violently with powerful oxidizers such as calcium hypochlorite. Thermal decomposition of thiocarbamate compounds include carbon disulfide, oxides of sulfur, oxides of nitrogen, hydrogen sulfide, ammonia, andmethylamine. Thio and dithiocarbamates 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

Land burial is acceptable for small quantities. Larger quantities can be incinerated. (EPTC is combustible and could be incinerated. Recommendable method: Incineration. Peer-review: Incineration in a unit witheffluent gas scrubbing is recommendable for large amount. Containers must be disposed of 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

InChI:InChI=1/C9H19NOS/c1-4-7-10(8-5-2)9(11)12-6-3/h4-8H2,1-3H3

Upstream product

• 201230-82-2 carbon monoxide 
• 75-03-6 ethyl iodide 
• 142-84-7 di-n-propylamine 
• 75-00-3 chloroethane 
• 62806-88-6 N,N-dipropylcarbamothioate sodium salt 
• 27086-19-7 N,N-dipropylcarbamoyl chloride 
• 64-67-5 diethyl sulfate 
• 1975-85-5 N,N-di-n-propyl O-ethyl thiocarbamate 
• 908126-51-2 di-n-propylammonium hydrogen sulphate 
• 140-90-9 sodium O-ethyl dithiocarbonate 
• 101622-02-0 S-vinyl N,N-di(n-propyl)-thiolcarbamate 
• 71280-90-5 Dipropyl-thiocarbamic acid; compound with dipropyl-amine 

Downstream Products

• 51892-58-1 S-ethyl dipropylthiocarbamate S,S-dioxide 
• 27086-19-7 N,N-dipropylcarbamoyl chloride 

Relevant academic research and scientific papers

New facile one-pot synthesis of S-alkyl thiolcarbamates from xanthogenate in water

A simple and efficient one-pot synthesis was developed for the preparation of S-alkyl thiolcarbamates from xanthogenate without catalyst using water as a solvent. The water can be recycled after removal of the product. The significant features of this protocol are: operational simplicity, mild reaction conditions, recycling of solvent and high product yields. Starting basic alkyl xanthogenate reacts with alkyl ammonium sulfate (aryl ammonium sulfate) and hydrogen peroxide (molar ratio 1:0.55:1) in water at 40 C for 1 h, followed by additional heating at 70-110 C for 1-2.3 h. Good to excellent yields were achieved using ammonium sulfate in 10 % molar excess. Graphical abstract: [Figure not available: see fulltext.]

LIQUID FORMULATIONS

The present invention relates to a liquid formulation comprising a) agrochemically active salts of 2-iodo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl]benzenesulfonamide, and b) one or more non-polar organic solvents selected from the group of the C6-C16-aromatics mixture the Solvesso series (Exxon) and/or the Caromax series (Carless), and also ?optionally further non-polar organic solvents. The liquid formulation is suitable for crop protection.

Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates

A new route to S-alkylcarbamothioates is disclosed. In a first step, N-(2-aminophenyl)-4-methyl-thiazolin-2-thione is transformed into a mono- or disubstituted urea at nitrogen, and then in a second step, alkylated at sulfur. The resulting salts, after treatment with a base, gave S-alkylcarbamothioates in high isolated yields together with 3-methyl[1,3]thiazolo[3,2-a]benzimidazole under very mild conditions.

Solvent-assisted thiocarboxylation of amines and alcohols with carbon monoxide and sulfur under mild conditions

DMSO or DMF as a solvent strongly accelerated the thiocarboxylation of amines and alcohols with carbon monoxide and sulfur. Under mild conditions (1 atm, 20°C), this thiocarboxylation of amines assisted by DMSO with carbon monoxide and sulfur has been developed into a practical and convenient synthetic method for S-alkyl thiocarbamates in good to excellent yields, including EPTC, thiobencarb, orbencarb, and molinate (herbicides). DMF also showed the similar solvent effect. NMP slightly decreased the effect for the thiocarboxylation of amines, and the yield of S-alkyl thiocarbamate was lowered in DMAc. Surprisingly, no formation of S-alkyl thiocarbamate was observed at the use of the other solvents, such as THF, hexane, toluene, AcOEt, MeCN, MeOH, and H 2O. The present solvent-assisted thiocarboxylation with carbon monoxide and sulfur could be also applied to a new synthesis of S-alkyl O-alkyl carbonothioates from alcohols under mild conditions (1 atm, 20°C) in DMF using DBU (1,8-diazabicyclo[5.4.0]undec-7-ene).

Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur

An industrial and economic carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamate herbicides. In the presence of potassium carbonate and solvent DMSO, S-alkyl thiocarbamates, such as thiobencarb and orbencarb (herbicides) are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1atm, 20°C).

Facile S-alkyl thiocarbamate synthesis by a novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur

A novel DBU-assisted carbonylation of amines with carbon monoxide and sulfur has been developed for the synthesis of S-alkyl thiocarbamates. In the presence of DBU (1,8-diazabicyclo[5.4.0]undec-7-ene), S-alkyl thiocarbamates are synthesized in excellent yields from amines, carbon monoxide, sulfur, and alkyl halides under mild conditions (1 atm, 20°C). In the absence of DBU, however, no formation of S-alkyl thiocarbamate is observed. The present DBU-assisted carbonylation can also be applied to new synthetic methods for benthiocarb and orthobencarb (herbicides) and carbamoyl chlorides.

Herbicidal compositions

The present invention relates to a herbicidal composition comprising a) one or more herbicidal active substances, b) one or more surfactants other than silicone surfactants, and c) one or more humectants. The composition according to the invention is outstandingly suitable for controlling a variety of harmful plants.

Herbicidal composition

The present invention relates to a herbicidal composition, comprising A) one or more compounds of the formula (I) 1in which Hal1 and Hal2 are identical or different halogen atoms, R1 is H, a cation or a C1-C20-carbon-containing radical and B) one or more surfactants, comprising as structural element at least 12 alkylene oxide units.

Soluble polymer based matrix for chemically active water insoluble components

This invention relates to a water soluble matrix composition comprising an anionic surfactant, a C6 to C18 alkyl pyrrolidone, urea and a water insoluble copolymer of vinyl pyrrolidone with not more than 50 wt. % of a comonomer selected from the group of an α-olefin, vinyl acetate, an acrylic or methacrylic acid ester and methacrylamide as a free flowing particulate solid which matrix is suitably mixed with a water insoluble, chemically active component, such as an agrochemical, to provide a clear sprayable film forming emulsion, such as a non-leachable film on a plant or other substrate surface. The invention also relates to the method of preparing the matrix and to the incorporation of an agrochemical concentrate and plant spray composition.

Novel synthesis of S-alkyl thiocarbamates from amines, carbon monoxide, elemental sulfur, and alkyl halides in the presence of a selenium catalyst

Carbonyl selenide easily reacted with elemental sulfur at low temperature to form carbonyl sulfide in a good yield, and reaction of ammonium salts of selenocarbamates with elemental sulfur brought about ready transformation to those of thiocarbamates. On the basis of the high catalytic activity of selenium for carbonylation of amines with carbon monoxide in addition to these important findings, a convenient new method for synthesis of S-alkyl thiocarbamates was developed through the carbonylation of amines with carbon monoxide and elemental sulfur in the presence of a selenium catalyst under mild conditions followed by alkylation of ammonium salts of the thiocarbamates with alkyl halides.