Pirimicarb

Pirimicarb Basic information
Product Name:Pirimicarb
Synonyms:O-(Dimethylamino-5,6-dimethylpirimidin-4-yl)-N,N-dimethyl carbamate;Piricarbe;PIRIMICARB, 1GM, NEAT;PIRIMICARB PESTANAL, 250 MG;pirimicarb (bsi,e-iso,ansi,jmaf);pirimicarb solution;pirimicarbe (f-iso);2-(DIMETHYLAMINO)-5,6-DIMETHYL-4-PYRIMIDINYLDIMETHYLCARBAMATE(PIRIMICARB)
CAS:23103-98-2
MF:C11H18N4O2
MW:238.29
EINECS:245-430-1
Product Categories:INSECTICIDE;Alpha sort;CarbamatesPesticides&Metabolites;Insecticides;N-PAlphabetic;P;PER - POLA;Pesticides
Mol File:23103-98-2.mol
Pirimicarb Structure
Pirimicarb Chemical Properties
Melting point 90.5°C
Boiling point 380.88°C (rough estimate)
density 1.1387 (rough estimate)
vapor pressure 2.1 x 10-3 Pa (30 °C)
refractive index 1.6081 (estimate)
Fp >100 °C
storage temp. APPROX 4°C
solubility Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
pka4.34 (weak base)
Water Solubility 3060 mg l-1
form neat
Merck 13,7579
BRN 663442
LogP1.700
CAS DataBase Reference23103-98-2(CAS DataBase Reference)
NIST Chemistry ReferencePirimicarb(23103-98-2)
EPA Substance Registry SystemPirimicarb (23103-98-2)
Safety Information
Hazard Codes T;N,N,T,Xn,F
Risk Statements 25-50/53-36-20/21/22-11
Safety Statements 22-37-45-60-61-36-26-16-36/37
RIDADR UN 2811
WGK Germany 3
RTECS EZ9100000
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data23103-98-2(Hazardous Substances Data)
ToxicityLD50 orally in female rats: 147 (mg/kg) (Baranyovits, Ghosh)
MSDS Information
ProviderLanguage
Pirimicarb English
Pirimicarb Usage And Synthesis
DescriptionPirimicarb is a colorless solid that is moderately soluble in water, acetone, ethanol, xylene, and chloroform.
Pirimicarb is produced by reaction of 2-dimethylamino- 5,6-dimethyl-4-pyrimidone with dimethylcarbamic acid chloride in the presence of a base or phosgene and dimethylamine. Pirimicarb is a systemic, selective aphicide used largely on grain crops, but also on ornamentals, cotton, fruit, and in greenhouses.
Chemical PropertiesColorless crystalline solid. Odorless. Commercial product may be available as a liquid
UsesPirimicarb is a systemic insecticide with contact, stomach and respiratory action. It is a selective aphicide used in cereals, fruit, ornamentals, strawberries, potatoes, sugar beet, fodder beet, cotton, oilseed rape, tobacco and glasshouse crops.
UsesInsecticide.
DefinitionChEBI: An aminopyrimidine that is N,N,4,5-tetramethylpyrimidin-2-amine substituted by a (dimethylcarbamoyl)oxy group at position 4.
Health HazardHighly toxic insecticide by oral and possibly other routes of entry; cholinesteraseinhibitor; median oral lethal doses in experimental animals ranged at 100–150 mg/kg;toxic symptoms include excessive salivation,lacrimation, slow heartbeat, blurred vision,headache, muscle twitching, tremor and convulsion; gastrointestinal effects include vomiting, nausea, abdominal pain, and diarrhea;severe poisoning can progress to death.
LD50 oral (rat): ~50 mg/kg
LD50 oral (dog): 100 mg/kg.

Agricultural UsesInsecticide: Originally registered in the U.S. for non-food use on alfalfa grown for seed in selected. Elsewhere it is used on a wide range of cereals, potatoes, fruits, vegetables and other crop.
Trade nameABOL®; AFICIDA®; APHOX®; FERNOS®; PIRIMIKARB; PIRIMOR®; PP 062®; PYRIMOR®; RAPID®
Potential ExposurePrimicarb is a carbamate (N-methyl) insecticide. Originally registered in the United States for non-food use on alfalfa grown for seed in selected. Elsewhere it is used on a wide range of cereals, potatoes, fruits, vegetables and other crop
Metabolic pathwayThe influence on the qualitative photochemical behavior of pirimicarb which leads to the photoproducts N-formylpirimicarb and demethylpirimicarb is modified by the waxes that are extracted from nectarines, oranges, and mandarin oranges. The formation of the photoproducts is hindered by the waxes.
ShippingUN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.
DegradationPirimicarb is hydrolysed in alkaline solutions (PM). Sterilised buffer solutions of unlabelled pirimicarb at pH values of 4,7 and 9 were incubated in the dark at 50 °C for 5 days. Samples were taken and analysed by HPLC. No hydrolysis of pirirnicarb was detected. At longer incubation times, some of the N-formyl derivative (2) (see Scheme 1) was produced (PSD, 1995). [14C-pyrimidinyl]Pirimicarb was dissolved in buffer solutions of pH 5,7 or 9 and exposed to natural sunlight (August in southern England) for up to 27 days. Losses of radioactivity by volatilisation were insignificant. After 3 weeks virtually all the pirimicarb was degraded. In neutral and acid solutions the main product was the N-formyl derivative (2). At pH 9 this was unstable. The N-monodemethylpirimicarb (3), aminopirimicarb (4) and the pyrimidinol(5) were also identified and some polar products were formed.
A further study under similar conditions (August 1974) afforded compounds 14 and the pyrimidinol derivatives (5, 6, 7). N,N-Dimethylguanidine (8), N-methylguanidine (9) and guanidine (10) were identified by electrophoretic methods. The guanidines were formed by opening of the pyrimidine ring (PSD, 1995). These pathways are illustrated in Scheme 1.
In other studies in which aqueous solutions or solid samples of pirimicarb were exposed to sunlight or lamps in the laboratory, the products 2, 3, 4 and 5 were also found, the first usually being the major product. Pirisi ef al. (1996) also detected a formylaminodimethylcarbamate (11) whilst Romero et al. (1994) reported that the formaminopyrimidinol (12) was formed via the N-formyl compound (2). [14C-pyrimidinyl]Pirimicarb was applied to a silty-clay loam on a thin-layer plate coated with soil. The plate was exposed under polythene to sunlight in southern England. Pirimicarb was completely degraded over 20 days. The major degradation product was the pyrimidinol (5) formed by hydrolysis of the carbamate ester group. No volatile products were detected (Hill, 1976; PSD, 1995).

IncompatibilitiesMay react with strong oxidizers such as chlorates, peroxides, and nitrates. May form explosive materials with phosphorus pentachloride.
Waste DisposalDo not discharge into drains or sewers. Dispose of waste material as hazardous waste using a licensed disposal contractor to an approved landfill. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Incineration with effluent gas scrubbing is recommended. 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.
Pirimicarb Preparation Products And Raw materials
Raw materialsIodomethane-->Ethyl acetoacetate-->Dimethylamine-->4-Hydroxypyrimidine-->1,1-DIMETHYLGUANIDINE SULFATE-->Ethyl crotonate-->methylguanidine
PIRIMICARB-DEMETHYL,PIRIMICARB-DESMETHYL,Desmethyl-pirimicarb, Pestanal,Pirimicarb III 2-Pyrimidinamine, N-methyl- (9CI) Dacthal Amino formate herbicide 6-METHYL-2-(METHYLAMINO)PYRIMIDIN-4-OL POLYURETHANE Desmethylformamide pirimicarb,Pirimicarb II PIRIMICARB-DESMETHYL-FORMAMIDO 2-Pyrimidinamine, 5-methyl- (9CI) DESMETHYL-FORMAMIDO-PIRIMICARB 5-METHYLPYRIMIDIN-4-OL 4(1H)-Pyrimidinone, 2-amino-5-methyl- (7CI,8CI,9CI) PIRIMICARB SOLUTION 100UG/ML IN ACETONITRILE 1ML 5,6-DIMETHYL-PYRIMIDIN-4-OL PIRIMICARB SOLUTION 100 NG/MYL IN 2-Amino-6-methyl-4-pyrimidinol PIRIMICARB-D6 DESMETHYL-PIRIMICARB

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