2212-67-1 Usage
Uses
Selective herbicide used to control the germination of annual grasses and broadleaved
weeds in rice crops.
General Description
Clear liquid with aromatic odor. Non corrosive. Used as an herbicide.
Reactivity Profile
Molinate is a thiocarbamate. Flammable gases are generated by the combination of thiocarbamates and dithiocarbamates with aldehydes, nitrides, and hydrides. Thiocarbamates and dithiocarbamates are incompatible with acids, peroxides, and acid halides.
Agricultural Uses
Herbicide: Molinate is a selective herbicide used on rice for the
control of water grass and other weeds.
Trade name
ARROSOLO?; FELAN?; HIGALNATE?;
HYDRAM?; JALAN?; MALERBANE-GIAVONI-L?;ORDAM?; ORDRAM?; R-4572?; RICECO;
SAKKIMOL?; STAUFFER R 4,572?; YALAN?; YULAN?
Environmental Fate
Soil. Hydrolyzes in soil forming ethyl mercaptan, carbon dioxide and dialkylamine
(half-life approximately 2–5 weeks) (Hartley and Kidd, 1987). At recommended rates of
application, the half-life of molinate in moist loam soils at 21–27°C is approximately 3
weeks (Humburg et al., 1989). Rajagopal et al. (1989) reported that under flooded conditions,
molinate was hydroxylated at the 3- and 4-position with subsequent oxidation
forming many compounds including molinate sulfoxide, carboxymethyl molinate, hexahydroazepine-
1-carbothioate, 4-hydroxymolinate, 4-hydroxymolinate sulfoxide, hexahydroazepine,
S-methyl hexahydroazepine-1-carbothioate, 4-ketomolinate, 4-hydroxyhexahydroazepine,
4-hydroxy-N-acetyl-hexahydroazepine, carbon dioxide and bound
residues.Plant. Molinate is rapidly metabolized by plants releasing carbon dioxide and naturally
occurring plant constituents (Humburg et al., 1989).Photolytic. Molinate in a hydrogen peroxide solution (120 mM) was irradiated by UV
light (l = 290 nm) at 23°C. The major photooxidation products were the two isomers of
2-oxomolinate (20% yield) and s-molinate oxide (5% yield) (Draper and Crosby, 1984).Half-lives of 180 and 120 hours were observed using one and two equivalents of hydrogen
peroxide, respectively (Draper and Crosby, 1984). Molinate has a UV absorption maximum
at 225 nm and no absorption at wavelengths >290 nm. Therefore, molinate is not expected
to undergo aqueous photolysis under natural sunlight (l = 290 nm). In the presence of
tryptophan, a naturally occurring photosensitizer, molinate in aqueous solution photodegraded
to form 1-((ethylsulfinyl)carbonyl)hexahydro-1H-azepine, S-ethyl hexahydro-2-
oxo-1H-azepine-1-carbothioate and hexamethyleneimine (Soderquist et al., 1977).Chemical/Physical. Metabolites identified in tap water were molinate sulfoxide, 3- and
4-hydroxymolinate, ketohexamethyleneimine and 4-ketomolinate (Verschueren, 1983).
Metabolic pathway
Juvenile white sturgeon and common carp are
exposed to 14C-molinate in a flow-through metabolism
system and oxidize molinate to form several products
and hydrolyze or conjugate with glutathione (GSH),
the sulfoxide, or sulfone. Both fish form a D-glucuronic
acid conjugate. The higher toxicity of molinate in
common carp may be due to greater bioconcentration,
slower depuration, and less efficient metabolic
deactivation. In the blood of common carp, molinate is
oxidized by erythrocytes to the sulfoxide and possibly
the sulfone, then conjugated with GSH or cysteine and
cleaved to form mercapturic acid in both erythrocytes
and plasma. Conjugation and possible hemoglobin
carbamylation occur only after sulfoxidation of
molinate. Molinate is distributed uniformly throughout
the soil layers, and its degradation products are identified as 2-oxomolinate, 4-oxomolinate, molinate
acid, and hexamethyleneimine. In rice plants,
4-hydroxymolinate, 2-oxomolinate, 4-oxomolinate,
S-ethyl-N-carboxymethylthiocarbamate, molinate acid,
and molinate alcohol are detected. By the soil
microorganisms, oxidation of the S-ethyl moiety is
considered to be the main pathway, and hydroxy and
oxoderivatives on the azepine ring are identified.
Check Digit Verification of cas no
The CAS Registry Mumber 2212-67-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,2,1 and 2 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 2212-67:
(6*2)+(5*2)+(4*1)+(3*2)+(2*6)+(1*7)=51
51 % 10 = 1
So 2212-67-1 is a valid CAS Registry Number.
InChI:InChI=1/C9H17NOS/c1-2-12-9(11)10-7-5-3-4-6-8-10/h2-8H2,1H3
2212-67-1Relevant articles and documents
Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives: a route to diversely substituted S-alkylcarbamothioates
Doukara, Abdallah Larbi,Mehdid, Mohammed Amine,Djafri, Ayada,Andreoli, Federico,Vanthuyne, Nicolas,Roussel, Christian
experimental part, p. 1852 - 1858 (2010/04/04)
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.
Practical synthesis of S-alkyl thiocarbamate herbicides by carbonylation of amines with carbon monoxide and sulfur
Mizuno, Takumi,Iwai, Toshiyuki,Ito, Takatoshi
, p. 2869 - 2873 (2007/10/03)
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).
Triazolecarboxamide herbicides
-
, (2008/06/13)
Compounds of the formula: STR1 wherein X is O or S; R and R1 are substituted or unsubstituted alkyl, alkenyl, alkynyl or cycloalkyl or R and R1 may be joined to form a heterocyclic ring; R2 is substituted or unsubstituted cycloalkyl; and n is 0, 1 or 2 are disclosed as well as their postemergence and preemergence selective herbicide use against both monocot and dicot weeds in crops such as sugarbeets, cotton, soybeans and rice.
