23103-98-2

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;Primicarb;pirimicarb (bsi,e-iso,ansi,jmaf);pirimicarb solution;pirimicarbe (f-iso)
• CAS NO: 23103-98-2
• Molecular Formula: C₁₁H₁₈N₄O₂
• Molecular Weight: 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
• Article Data: 4

Chemical Properties

• Melting Point: 90.5°C
• Boiling Point: 380.88°C (rough estimate)
• Flash Point: >100 °C
• Appearance: white crystal
• Density: 1.1387 (rough estimate)
• Vapor Pressure: 8.99E-06mmHg at 25°C
• Refractive Index: 1.6081 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: 4.34 (weak base)
• Water Solubility: 3060 mg l-1
• Merck: 13,7579
• BRN: 663442
• CAS DataBase Reference: Pirimicarb(CAS DataBase Reference)
• NIST Chemistry Reference: Pirimicarb(23103-98-2)
• EPA Substance Registry System: Pirimicarb(23103-98-2)

Safety Data

• Hazard Codes: T;N,N,T,Xn,F
• 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 Data: 23103-98-2(Hazardous Substances Data)

Usage

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

Uses

Different sources of media describe the Uses of 23103-98-2 differently. You can refer to the following data:
1. Insecticide.
2. 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/kgLD50 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?

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

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.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required.

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).

Incompatibilities

May react with strong oxidizers such as chlorates, peroxides, and nitrates. May form explosive materials with phosphorus pentachloride.

InChI:InChI=1/C11H18N4O2/c1-7-8(2)12-10(14(3)4)13-9(7)17-11(16)15(5)6/h1-6H3

Downstream Products

• 30614-21-2 2-(amino)-5,6-dimethylpyrimidin-4-yldimethylcarbamate 
• 30614-22-3 2-(methylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate 
• 40778-16-3 2‐dimethylamino‐5,6‐dimethyl‐4‐hydroxypyrimidine 
• 27218-04-8 2-<(methylformyl)amino>-5,6-dimethylpyrimidin-4-yl dimethylcarbamate 
• 178273-91-1 2-(formylamino)-5,6-dimethylpyrimidin-4-yl dimethylcarbamate 
• 74-89-5 methylamine 

Relevant articles and documents

SYSTEM FOR PROTECTING GOODS DURING TRANSPORT

A system for protecting stored goods in a container (10), comprises a cage-like structure (20) formed by at least one pesticide treated net (22), capable of enclosing the stored goods, wherein the cage like structure (20), further comprises means for suspending the pesticide treated nets (14, 28, 30, 32, 34), and means for opening and closing the cage-like structure (26) on at least one section (24) of the at least one net (22). The system is particularly useful for the transport of tobacco, coffee, dried fruits, cocoa, nuts, tea, cereals, vegetables, spices and animals.

Use of citric acid derivatives as pesticidal adjuvants

The invention provides the use as a pesticidal adjuvant of at least one citric acid derivative and compositions containing the derivative, which has a log octanol-water coefficient (log P) of 2.6 to 11 and an equivalent hydrocarbon (EH) value of 29 to 47. The invention has been shown to enhance the efficacy of a range of pesticides.