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Home > Encyclopedia > Pirimicarb

Pirimicarb

Pirimicarb structure

Pirimicarb 

structure
  • CAS No:

    23103-98-2

  • Formula:

    C11H18N4O2

  • Chemical Name:

    Pirimicarb

  • Synonyms:

    Carbamic acid,N,N-dimethyl-,2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl ester;Carbamic acid,dimethyl-,2-(dimethylamino)-5,6-dimethyl-4-pyrimidinyl ester;4-Pyrimidinol,2-(dimethylamino)-5,6-dimethyl-,dimethylcarbamate (ester);Pirimicarb;PP 062;5,6-Dimethyl-2-dimethylamino-4-dimethylcarbamoyloxypyrimidine;Pirimor;2-Dimethylamino-5,6-dimethyl-4-pyrimidinyl dimethylcarbamate;2-Dimethylamino-5,6-dimethylpyrimidin-4-yl N,N-dimethylcarbamate;Fernos;Pyrimor;Pirimor G;Pirimor Granulate;Aphox;Pirimix;Aphox DG;Aficida;Patton Flow

  • Categories:

    Agrochemicals  >  Insecticides

Description

Colorless crystalline solid. Odorless. Commercial product may be available as a liquid


Pirimicarb is an aminopyrimidine that is N,N,4,5-tetramethylpyrimidin-2-amine substituted by a (dimethylcarbamoyl)oxy group at position 4. It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, a carbamate insecticide, an agrochemical, an environmental contaminant, a xenobiotic and an insecticide. It is a carbamate ester, an aminopyrimidine and a tertiary amino compound. It derives from a dimethylcarbamic acid.

Pirimicarb Basic Attributes

238.29

238.29

245-430-1

1I93PS935T

2757

DTXSID1032569

Colorless solid

2933599015

Characteristics

58.6

1.7

white crystal

1.21 g/cm3

90.5 °C

373.4±52.0 °C at 760 mmHg

>100 °C

1.549

In water, 2,700 mg/l @ 25 deg C

APPROX 4°C

2.1 x 10 -3 Pa (30 °C)

Oral-Rat  LD50: 100 mg/kg; Oral-Mouse LD50: 107 mg/kg

Combustion produces toxic nitrogen oxide gas

pKa = 4.53

154.68 Ų [M+H]+ [CCS Type: TW]|155.9 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated]|156.23 Ų [M+H]+

Safety Information

III

6.1(b)

UN 2811

3

25-50/53-36-20/21/22-11

22-37-45-60-61-36-26-16-36/37

EZ9100000

T;N,N,T,Xn,F

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

Compatible with most common, neutral insecticides, fungicides, & acaricides.

P273-P501

H301-H410

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P308+P313, P311, P321, P330, P333+P313, P363, P391, P403+P233, P405, and P501|H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]|Aggregated GHS information provided by 322 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P305+P351+P338, P309+P311, P310, P312, P314, P320, P321, P322, P330, P337+P313, P361, P363, P403+P233, P405, and P501

/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Health: TOXIC; may be fatal if inhaled, ingested or absorbed through skin. Inhalation or contact with some of these materials will irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion and poison hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|/GUIDE 131: FLAMMABLE LIQUIDS-TOXIC/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Carbamate pesticide, liquid, flammable, poisonous; Carbamate pesticide, liquid, flammable, toxic; Carbamate pesticide, liquid, poisonous, flammable; Carbamate pesticide, liquid, toxic, flammable/|For more DOT Emergency Guidelines (Complete) data for PIRIMICARB (16 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

highly toxic

Thiram applied in an equitoxic mixture with pirimicarb evidently intensifies and prolongs the neurochemical effect of pirimicarb in the rat.

LD50 Rat (female) oral 68-221 mg/kg|LD50 Mouse (female) oral 107 mg/kg|LD50 Dog oral 100-200 mg/kg|LD50 Rat (female) dermal >500 mg/kg|For more Non-Human Toxicity Values (Complete) data for PIRIMICARB (8 total), please visit the HSDB record page.

/AQUATIC SPECIES/ Tadpoles of Rana perezi were kept for 14 weeks in water containing two sublethal levels of the carbamate insecticide ZZ-Aphox or the organophosphate Folidol. Approx concns of their active ingredients were 0.25 and 1 mg/l. Resulting malformations were studied by skeletal analysis and histological and histochemical investigation of the rear limbs of the tadpoles. The pesticides caused the animals to have malformations of the spinal column (scoliosis) and/or limbs (short and thick long bones with the epiphyses grossly twisted). Histochemical study showed differences in the composition of the connective matrix, and microscopic exam of the long bones indicated alterations in the thickness of the uncalcified bone matrix (osteoid) and the presence of abundant vascularised connective tissue in the region of the periosteum. The results confirmed changes in the composition of the connective tissue matrix as the cause of the defects observed in bone formation which are also discussed in relation to vitamin D absorption and calcium homeostasis.|/AQUATIC SPECIES/ In tests with newborn and 1-wk-old Daphnia magna, 48-hr EC50 values of 21-24 ug/L and 16 ug/L pirimicarb, respectively, were found.|/FIELD STUDIES/ Pirimicarb is registered for use within cereals ... /and was/ field-tested for toxicity to beneficial nontarget invertebrate groups important as food for farmland birds. Compared to the control, pirimicarb was the least toxic for most invertebrate groups examined. ...Toxicity was further tested on larvae of graminivorous sawflies, an important chick- food group, using field-sprayed plants in laboratory and semifield trials. None of the pyrethroid and carbamate compounds and mixtures was as toxic as the organophosphate, but all were more toxic than the control. The semifield experiments provided a useful way of determining potential insecticide impact on this nontarget group where field populations are often too low for field trials to have statistically conclusive results.

Pirimicarb's production may result in its release to the environment through various waste streams; it's use as an insecticide(1) will result in its direct release to the environment(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 56-800(2,3), indicate that pirimicarb is expected to have high to low mobility in soil(SRC). Soils with a high clay content and low percentage of organic matter tend to sorb pirimicarb stronger than do soils with a high content of organic matter(SRC). Pirimicarb is a weak base with a pKa of 4.54(4), suggesting that it will partially exist in the protonated form in moist soils(SRC). Volatilization of pirimicarb from moist soil surfaces is not expected to be an important fate process(SRC) because cations do not volatilize and given an estimated Henry's Law constant for the free base of 8.4X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 7.28X10-6 mm Hg(4), and water solubility, 2,700 mg/l(4). Pirimicarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure of 7.28X10-6 mm Hg(4). Biodegradation data on pirimicarb in soils suggests that the rate of degradation varies greatly depending upon the conditions of the soil(SRC), with half-lives ranging from several days to several months(4,6-8).|AQUATIC FATE: Based on a classification scheme(1), Koc value ranging from 56-800, measured in different soils(2,3), indicates that pirimicarb is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 8.4X10-10 atm-cu m/mole(SRC), based upon its vapor pressure, 7.28X10-6 mm Hg(5), and water solubility, 2,700 mg/l(6). Furthermore, pirimicarb is a weak base with a pKa of 4.53(12). This pKa indicates that pirimicarb will partially exist in the protonated form in the environment and cations do not volatilize(SRC). According to a classification scheme(7), an estimated BCF of 4(SRC), from a measured log Kow of 1.7(5) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). No biodegradation data exist for pirimicarb in water(SRC), but data in soil shows that biodegradation varies greatly by location and type of soil, with half-lives ranging from several days to several months(5,9-11). Photolysis in sunlit surface water may be an important fate process for pirimicarb based on a photolysis half-life of less than 1 day in aqueous solution(5). Hydrolysis occurs slowly in the environment with a measured half-life of over 23 days in a water/sediment system(5).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pirimicarb, which has a vapor pressure of 7.28X10-6 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the particulate phase in the ambient atmosphere. Vapor-phase pirimicarb is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2 hours(SRC), calculated from its rate constant of 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase pirimicarb may be removed from the air by wet and dry deposition(SRC). Pirimicarb undergoes photolysis in aqueous solutions exposed to UV light with a half-life of less than 1 day(2), which suggests direct photolysis in the atmosphere is also possible(SRC).

The rate constant for the vapor-phase reaction of pirimicarb with photochemically-produced hydroxyl radicals has been estimated as 1.5X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pirimicarb undergoes photolysis in the environment with a half-life of less than 1 day in aqueous solutions exposed to UV light(2). Hydrolysis occurs slowly in the environment with a measured half-life of over 23 days in a water/sediment system(2).

An estimated BCF of 4 was calculated for pirimicarb(SRC), using a log Kow of 1.7(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

79.43 L/kg|The Koc of pirimicarb in soil was reported as 1,387(1), but no details of the soil conditions were provided and the adsorption of pirimicarb is greatly dependent upon the characteristics of the soil(SRC). The adsorption of pirimicarb in 21 different soils was studied(2). The greatest adsorption was observed in soils with a high clay content and low percentage of organic matter(2). Relatively weak adsorption was observed in soils containing a high percentage of organic carbon(2). Using the adsorption coefficient (Kd) and percentage of organic carbon present in the soil, Koc values ranging from about 56 to 270 were calculated for soils with organic carbon content of 1% or greater(SRC). The mobility of pirimicarb was significantly attenuated by soils with a large percentage of clay and a low percentage of organic matter(SRC). The mobility of pirimicarb was studied in 10 soils and smectites(3). Using the adsorption coefficient (Kd) and percentage of organic carbon present in the soil, Koc values of 270 and 800 were calculated for 2 soils with organic carbon content of approximately 1%(SRC). The adsorption was significantly greater in the other 8 soils with a low percentage of organic matter(SRC). According to a classification scheme(4), these Koc values suggest that pirimicarb is expected to have high to low mobility in soil depending upon the conditions(SRC). Pirimicarb was shown to have low mobility in experiments conducted with cultivated and uncultivated sandy loams having pH 6.7 and organic matter of 2.27%(5). Approximately 53-66% of the initially applied 14C-Pirimicarb remained in the upper layer (0-1 cm) of these soils after 7 days with less than 10 % migrating to the lower layer (4-10 cm depth)(5). Other experiments using a sandy loam from northern China (pH 8.6, 1.8% organic matter) showed that pirimicarb was weakly sorbed to the soil surface(6).

Pirimicarb is a weak base with pKa of 4.53(5). This pKa indicates that pirimicarb will partially exist in the protonated form in the environment(SRC). The Henry's Law constant for pirimicarb as the free base is estimated as 8.4X10-10 atm-cu m/mole(SRC) based upon its vapor pressure, 7.28X10-6 mm Hg(1), and water solubility, 2,700 mg/l(2). This Henry's Law constant and the fact that cations are non-volatile indicates that pirimicarb is expected to be essentially nonvolatile from water surfaces and soil surfaces(3). Pirimicarb is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1). Pirimicarb was applied to the surface of a soil and leaves of a French bean plant and studied in a fume hood (air velocity 2 m/s, 13-21 °C in plant experiments and 1 m/s, 19-26 °C in soil experiments) under laboratory conditions(4). After 24 hours 89.5 % of the original pirimicarb was recovered from the soil and 47.4 % of the initial amount was recovered from the leaves(4).

SURFACE WATER: Pirimicarb was detected at a concn of 4 ug/l in surface water near a barley field where it was applied(1). Pirimicarb was detected in water samples of a stream near an agricultural field in Sweden at mean concns of 0.22 ug/l (1990) and 0.02 ug/l (1991)(3). GROUND WATER: Pirimicarb was detected in 2 out of 12 groundwater samples of the Hojvads Rende catchment area, Denmark at concns of less than 0.1 ug/l(5). RAIN/SNOW: Pirimicarb was identified in 19% of the rainfall samples obtained in Germany(2). Pirimicarb was detected in rainfall samples from Greece at concns of 0.08-0.42 ug/l(4).

Pirimicarb was detected in lettuce at concns of 0.04-15.65 ppm(1) and grapes at a concn of 0.11 ppm(2). Pirimicarb was detected in 3 agricultural commodities at a concn of 0.1 ppm and 1 commodity at a concn of 0.05 ppm during a 1982-1986 study on domestic and imported food products(3).

Occupational exposure to pirimicarb may occur through inhalation and dermal contact with this compound at workplaces where pirimicarb is produced or used. Monitoring data indicate that the general population may be exposed to pirimicarb via ingestion of food products containing pirimicarb. (SRC)

Drug Information

Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics. (See all compounds classified as Insecticides.)

In rats given carbonyl-labeled [14C]pirimicarb by gavage or ip injection, >50% of the dose was expired as 14CO2 within 5 hr, & 15% was eliminated in the urine; essentially no residues were detected at sacrifice 8 days after admin. Up to 4 daily admins of pirimicarb to rats resulted in no accumulation in adipose tissue. In dogs, 86-94% of a ring-14C-labeled dose of pirimicarb was recovered, 79-88% in the urine & 6-7% in the feces; recovery was 74-86% after 1 day. Of a carbonyl-labeled dose to dogs, 15-26% was recovered, primarily in the urine; the unrecovered portion was thought to be expired rapidly as 14CO2. Of pirimicarb admin to a lactating dairy cow, 96% of the dose appeared in the urine, 4% in the feces, & <0.3% in the milk.|Mode of action: Selective systemic insecticide with contact, stomach, and respiratory action. Absorbed by the roots, and translocated through the xylem. Penetrates the leaves, but is not translocated extensively.

Pirimicarb's major urinary metabolites in rats, dogs, & cows were similar, resulting from oxidative & hydrolytic mechanisms & consisting primarily of hydroxypyrimidines with modifications of the alkyl constituents of the heterocyclic moiety. Of the administered dose, 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine accounted for 10-16.3%, 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine for 20.5-41%, 2-amino-5,6-dimethyl-4-hydroxypyrimidine for 12.9-21%, & 2-dimethylamino-6-hydroxymethyl-5-methyl-4-hydroxypyrimidine for 1.8-5.7%. The major metabolites were eliminated unconjugated.|... During ... metabolism /of pirimicarb/ in mammals the carbamate moiety is hydrolyzed & subsequent demethylation at the dimethylamino group which is attached to the heterocyclic moiety results in the following major metabolites which are excreted in urine: 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine (DDHP), 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine (MDHP), & 2-amino-5,6-dimethyl-4-hydroxypyrimidine (ADHP). These metabolites were detected in every urine sample of seven workers who had applied pirimicarb. Concns of the 2-methylamino-5,6-dimethyl-4-hydroxypyrimidine & 2-amino-5,6-dimethyl-4-hydroxypyrimidine were much higher than that of 2-dimethylamino-5,6-dimethyl-4-hydroxypyrimidine indicating a considerable demethylation capacity in humans. No metabolites were found in urine specimens of controls. The investigated pyrimidines represent sensitive & specific parameters for biological monitoring of exposure to pirimicarb.

Cholinesterase inhibitor.

Basic treatment: Establish a patent airway. Suction if necessary. Aggressive airway control may be needed. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Carbamates and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. For hypotension if signs of hypovolemia are present, administer fluid cautiously. Watch for signs of pulmonary edema ... . Administer atropine. Correct hypoxia before administration ... . In severely poisoned patients, administer pralidoxime chloride (2 PAM). DIRECT PHYSICIAN ORDERS ONLY ... . Treat seizures with adequate atropinization and correction of hypoxia. Rarely is diazepam necessary ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Carbamates and related compounds/|Airway protection. Ensure that a clear airway exists. Intubate the patient and aspirate the secretions with a large-bore suction device if necessary. Administer oxygen by mechanically assisted pulmonary ventilation if respiration is depressed. Improve tissue oxygenation as much as possible before administering atropine, to minimize the risk of ventricular fibrillation. In severe poisonings, it may be necessary to support pulmonary ventilation mechanically for several days. /N-methyl carbamate insecticides/|Atropine. Administer atropine sulfate intravenously, or intramuscularly if intravenous injection is not possible. Remember that atropine can be administered through an endotracheal tube if initial IV access is difficult to obtain. Carbamates usually reverse with much smaller dosages of atropine than those required to reverse organophosphates. The objective of atropine antidotal therapy is to antagonize the effects of excessive concentrations of acetylcholine at end-organs having muscarinic receptors. Atropine does not reactivate the cholinesterase enzyme or accelerate excretion or breakdown of carbamate. Recrudescence of poisoning may occur if tissue concentrations of toxicant remain high when the effect of atropine wears off. Atropine is effective against muscarinic manifestations, but is ineffective against nicotinic actions, specifically, muscle weakness and twitching, and respiratory depression. Despite these limitations, atropine is often a life-saving agent in N-methyl carbamate poisonings. Favorable response to a test dose of atropine ... given intravenously can help differentiate poisoning by anticholinesterase agents from other conditions such as cardiogenic pulmonary edema and hydrocarbon ingestion. However, lack of response to the test dose, indicating no atropinization (atropine refractoriness), is characteristic of moderately severe to severe poisoning and indicates a need for further atropine. If the test dose does not result in mydriasis and drying of secretions, the patient can be considered atropine refractory. /N-methyl carbamate insecticides/|For more Antidote and Emergency Treatment (Complete) data for PIRIMICARB (15 total), please visit the HSDB record page.

/HUMAN EXPOSURE STUDIES/ Workers in the manufacture of formulated pirimicarb products showed transient cholinergic signs & depressed plasma cholinesterase activity. Investigation of plant procedures indicated that the workers had inhaled vapors generated when pirimicarb volatilized at high temperatures (65 °C). This occupational exposure had no evident long-term effects.|/HUMAN EXPOSURE STUDIES/ Pirimicarb exposure in 5 men employing low-volume application methods in commercial greenhouse operations was estimated. Using the video imaging technique (VITAE) for visualization and quantification of dermal exposure, the authors were able to show that failure to use precautionary handling methods resulted in non-uniform deposition of tracer/pesticide mixtures on various parts of the body. Estimates of pirimicarb exposure using the VITAE method correlated highly with excretion of urinary metabolites. The visual results provided by the VITAE system also proved to be a powerful educational tool in helping them adopt precautionary application techniques. The need to employ protective operating procedures when handling pesticides was demonstrated, no matter how brief the exposure period.|/HUMAN EXPOSURE STUDIES/ A battery of neurological and neurobehavior tests were administered to 137 applicators with pesticide exposure of >10 yr (avg 20 yr), and compared the results to 73 controls. Significant effects were found on peripheral nerve function parameters, in measures of attention and perceptual coding, and on the amount of beta-activity in EEGs. For the majority of the subjects, these effects were small. Exam of the exposed workers showed a number of them with cutaneous allergy to pesticides, although no differences in prevalence of symptoms was reported and measure of liver and renal function were within normal limits.|/HUMAN EXPOSURE STUDIES/ ... Workers at five commercial chrysanthemum operations were video imaged prior to debudding plants which had been treated with a fluorescent tracer and the pesticide, pirimicarb, 36-48 hr earlier. After 1-4 hr of debudding, workers were again imaged and the rates of tracer deposition determined with the /Video Imaging Technique to Assess Exposure/(VITAE) system. Tracer deposition from contact with treated foliage ...increased ...linear/ly/ ... over 4 hr. Greatest deposition occurred on the hands and arms and represented 42% and 20% of total exposure, respectively. No detectable air residue samples of pirimicarb were found while workers were debudding plants. Monitoring of four workers for pirimicarb and its urinary metabolites revealed no detectable residues following 4 hr of contact with foliage, which had been treated 48 hr earlier.|For more Human Toxicity Excerpts (Complete) data for PIRIMICARB (6 total), please visit the HSDB record page.

2-dimethylamino-5,6-dimethylpyrimidin-4-yldimethylcarbamate

Pirimicarb Use and Manufacturing

Methods of Manufacturing

Preparation Method 1 N, N-dimethylguanidine is prepared by reacting thiourea with dimethyl sulfate and then reacting with dimethylamine or dimethylamine hydrochloride to obtain N, N-dimethylguanidine. Preparation of ethyl α-methylacetoacetate Ethyl ethyl acetoacetate was methylated with dimethyl sulfate or methyl iodide to prepare ethyl α-methylacetoacetate. Ethyl α-methylacetoacetate can also be prepared by ethyl dimethylaminobutenoate. The reaction process is: (95%) (80%) 2-dimethylamino-5, 6-dimethyl-4- Preparation of hydroxypyrimidine Mix 14g of N, N-dimethylguanidine (sulfate) with 4.6g of acid-binding agent and alcohol, stir for 2h, add α-methylacetoacetate and solvent, and slowly warm up with stirring, at 140 The reaction was carried out at about ℃ for 2h. The solvent was recovered under reduced pressure. The solid was dissolved in chloroform and the pH was adjusted to 7. The chloroform was concentrated to dryness to obtain 15.7g of the product, with a content of 92.69% and a yield of 93.43%. 2-Dimethylamino-5, 6-dimethyl-4-hydroxypyrimidine can also be prepared by reacting formaldehyde with zinc acetate as a catalyst under pressurized conditions. The synthesis of anti-aphicarb is based on the general synthesis method of carbamate pesticides: Preparation method 2 In 35mL benzene solution containing 12.5% ​​phosgene, add 7.1g 5, 6-dimethyl-2-dimethylamino-4-hydroxypyrimidine A solution of 4.3g of triethylamine in benzene (100mL) was reacted at 5-8°C for 45min. 10mL of an aqueous solution containing 3.9g of dimethylamine was added dropwise and stirred. The reaction temperature was less than 10°C. Then stir at 10°C for more than 30 min and add 50 mL of water until all solids are dissolved. Separate benzene, wash with water, and add saturated Na2CO3 solution to obtain aphicarb, mp88~90℃.

Uses

Insecticide.

USEPA/OPP Pesticide Code 106101; Trade Names: Pirimor, PP 062, Pirimicarb technical.|Abol /trade name/|Aficida /trade name/|Aphox /trade name/|For more Formulations/Preparations (Complete) data for PIRIMICARB (7 total), please visit the HSDB record page.

FDA Method 232.4. Organophosphorous Residues General Methods for Nonfatty Foods Using Acetone Extraction and Isolation in Organic Phase. No detection limit.|FDA Method 242.1. Organonitrogen Residues General Method for Nonfatty Foods Including Acetone Extraction and Isolation in Organic Phase. No detection limit.

Agrochemicals -> Insecticides|Insecticides|Environmental transformation -> Pesticides (parent, predecessor)

Pirimicarb has known environmental transformation products that include 2-dimethylamino-5,6-dimethylpyrimidin-4-ol, 5,6-dimethyl-2-(methylamino)pyrimidin-4-ol, and 5,6-dimethyl-2-(methylformamido)pyrimidin-4-yl dimethylcarbamate.|Pirimicarb has known environmental transformation products that include Desmethyl-Pirimicarb, RO34836, R016192, R016210, R031805, R034865, R034885, and R35140.

Computed Properties

Molecular Weight:238.29
XLogP3:1.7
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:3
Exact Mass:238.14297583
Monoisotopic Mass:238.14297583
Topological Polar Surface Area:58.6
Heavy Atom Count:17
Complexity:270
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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