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Molinate

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Molinate Basic information
Molinate Chemical Properties
  • Melting point:<25 °C
  • Boiling point:202°C (10 mmHg)
  • Density 1.06
  • refractive index 1.5250 (estimate)
  • Flash point:100 °C
  • storage temp.  0-6°C
  • pka-1.22±0.20(Predicted)
  • form Liquid
  • color Amber
  • Water Solubility 0.08 g/100 mL
  • BRN 1239196
  • CAS DataBase Reference2212-67-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceMolinate(2212-67-1)
  • EPA Substance Registry SystemMolinate (2212-67-1)
Safety Information
  • Hazard Codes T,N,Xn
  • Risk Statements 20/22-40-43-48/22-63-50/53-62
  • Safety Statements 36/37-46-60-61
  • RIDADR 2902
  • WGK Germany 3
  • RTECS CM2625000
  • HazardClass 6.1(b)
  • PackingGroup III
  • Hazardous Substances Data2212-67-1(Hazardous Substances Data)
  • ToxicityLC50 (96-hour) for bluegill sunfish 29–30 mg/L, goldfish 30 mg/L, mosquito fish 16.4 mg/L, rainbow trout 0.2–1.3 mg/L (Hartley and Kidd, 1987); acute oral LD50 of technical molinate for rats and mice 720 and 795 mg/kg, respectively (Ashton and Monaco, 1991), 501 mg/kg (RTECS, 1985).
MSDS
Molinate Usage And Synthesis
  • UsesSelective herbicide used to control the germination of annual grasses and broadleaved weeds in rice crops.
  • General DescriptionClear liquid with aromatic odor. Non corrosive. Used as an herbicide.
  • Air & Water ReactionsWater soluble. Thio and dithiocarbamates slowly decompose in aqueous solution to form carbon disulfide and methylamine or other amines. Such decompositions are accelerated by acids.
  • Reactivity ProfileMolinate 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 UsesHerbicide: Molinate is a selective herbicide used on rice for the control of water grass and other weeds.
  • Trade nameARROSOLO®; FELAN®; HIGALNATE®; HYDRAM®; JALAN®; MALERBANE-GIAVONI-L®;ORDAM®; ORDRAM®; R-4572®; RICECO; SAKKIMOL®; STAUFFER R 4,572®; YALAN®; YULAN®
  • Environmental FateSoil. 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 pathwayJuvenile 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.
Molinate Preparation Products And Raw materials
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