| Identification | More | [Name]
Pirimicarb | [CAS]
23103-98-2 | [Synonyms]
2-DIMETHYLAMINO-5,6-DIMETHYL-4-PYRIDIMINYL DIMETHYL CARBAMATE
2-(DIMETHYLAMINO)-5,6-DIMETHYL-4-PYRIMIDINYL DIMETHYLCARBAMATE
APHOX
Aphox powder
Dimethylamino-5,6-dimethylpyrimidin-4-yl N,N-dimethylcarbamate
'LGC' (1626)
PILLY
PIRIMICARB
Pirimicarb powder(content>75%)
Pirimo powder
PIRIMOR
PIRIMOR(R)
TOMBA
2-Dimethylamino-5,6-dimethylpyrimidin-4-yl dimethylcarbamate
5,6-Dimethyl-2-dimethylamino-4-dimethylcarbamoyloxypyrimidine
5,6-Dimethyl-2-dimethylamino-4-pyrimidinyldimethylcarbamate
5,6-Dimethyl-2-dimethylamino-4-pyrimidinyl-dimethylcarbamate
5,6-dwumetylo-2-dwumetyloamino-4-pirimidynylodwukarbaminian
Abol
Aficida | [EINECS(EC#)]
245-430-1 | [Molecular Formula]
C11H18N4O2 | [MDL Number]
MFCD00055520 | [Molecular Weight]
238.29 | [MOL File]
23103-98-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Colorless crystalline solid. Odorless. Commercial product may be available as a liquid | [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) | [form ]
neat | [pka]
4.34 (weak base) | [Water Solubility ]
3060 mg l-1 | [Merck ]
13,7579 | [BRN ]
663442 | [LogP]
1.700 | [CAS DataBase Reference]
23103-98-2(CAS DataBase Reference) | [NIST Chemistry Reference]
Pirimicarb(23103-98-2) | [EPA Substance Registry System]
23103-98-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T;N,N,T,Xn,F | [Risk Statements ]
R25:Toxic if swallowed.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36:Irritating to the eyes.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S22:Do not breathe dust .
S37:Wear suitable gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 2811 | [WGK Germany ]
3 | [RTECS ]
EZ9100000 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [Hazardous Substances Data]
23103-98-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in female rats: 147 (mg/kg) (Baranyovits, Ghosh) |
| Hazard Information | Back Directory | [Potential Exposure]
Primicarb 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 | [First aid]
Speed in removing material from eyes and skin is of extreme importance. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 2448 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy. | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. | [Incompatibilities]
May react with strong oxidizers such as chlorates, peroxides, and nitrates. May form explosive materials with phosphorus pentachloride. | [Description]
Pirimicarb 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 Properties]
Colorless crystalline solid. Odorless. Commercial product may be available as a liquid | [Waste Disposal]
Do 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. | [Uses]
Insecticide. | [Uses]
Pirimicarb 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. | [Definition]
ChEBI: An aminopyrimidine that is N,N,4,5-tetramethylpyrimidin-2-amine substituted by a (dimethylcarbamoyl)oxy group at position 4. | [Health Hazard]
Highly 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 Uses]
Insecticide: 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 name]
ABOL®; AFICIDA®; APHOX®; FERNOS®; PIRIMIKARB; PIRIMOR®; PP 062®; PYRIMOR®; RAPID® | [Metabolic pathway]
The 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. | [Degradation]
Pirimicarb 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). |
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