29232-93-7CCN(CC)c1nc(C)cc(OP(=S)(OC)OC)n1QHOQHJPRIBSPCY-UHFFFAOYSA-NPirimiphos-methyl is a yellow liquid. Corrosive to tin and mild steel. Used as an insecticide.
Pesticides
Pesticide -> EPA IRIS
Insecticides
Active substance -> EU Pesticides database: Approved
Pesticides -> Organophosphate Insecticides
Environmental transformation -> Pesticides (parent, predecessor)
log Kow = 4.12
3.8
In water (mg/L at 20 °C): 11 (pH 5); 10 (pH 7); 9.7 (pH 9)
In water, 5 mg/L at 30 °C
Miscible with most organic solvents
Decomposes on distillation
decomposes
When heated to decomposition it emits very toxic fumes of /nitrogen, phosphorus, and sulfur oxides/.
Decomposes on distillation. ... /Decomposition time/ 50 7.5-35 days (pH range 5.8-8.5, most stable at pH 7). In sunlight, aqueous soln had DT50 1 day.
安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P270, P273, P301+P317, P319, P330, P391, and P501 (click each P-code to see the statement)
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P260, P264, P264+P265, P270, P273, P280, P301+P317, P302+P352, P305+P351+P338, P308+P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)
Hazard Traits - Developmental Toxicity; Environmental tox; Neurotoxicity
Commission Regulation (EC) No 451/2000
Pirimiphos-methyl is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
07/52/EC, Reg. (EU) 2018/917, Reg. (EU) 2019/707, Reg. (EU) 2020/869, Reg. (EU) 2021/745, Reg. (EU) 2022/708, Reg. (EU) 2023/918, Reg. (EU) 2025/787, Reg. (EU) No 540/2011
REACH registered substance: Pirimiphos-methyl (EC: 249-528-5)
Pirimiphos methyl: Does not have an individual approval but may be used under an appropriate group standard
Effects observed in two week study with rats include weight loss, decreased hemoglobin, and reticulocytosis; Minor reversible bile duct proliferation and liver damage observed in 90 day feeding study with dogs; Caused minor skin and eye irritation in rabbits; No evidence of skin sensitization in guinea pigs; [HSDB] The average of two baseline respective cholinesterase activity determinations three days apart, with no exposures to enzyme inhibiting pesticides for at least 30 days, is recommended for each worker prior to exposure to cholinesterase inhibitors because of large inter-individual differences in published baseline values. To be established at least once a year. Removal from workplace exposures is recommended until the cholinesterase activity returns to within 20% of baseline. [TLVs and BEIs]
Systemically, pirimiphos-methyl inhibits cholinesterase, & this is the only known mechanism of its toxic action. In spite of its rapid absorption, rats, given a dosage of 1,450 mg/kg, did not show clear signs of poisoning until 24 hr later, when their brain cholinesterase was inhibited by 46%. Recovery of cholinesterase activity began to be apparent in 72 hr; it was complete for plasma enzyme by 96 hr but was slower for the red cell enzyme.
Female rats given 2-(14)C-pirimiphos-methyl at a dose of 7.5 mg/kg bw orally were bled (cardiac puncture, three rats per time interval) at 0.5, 1, 3, 5, 7 or 24 hr after dosing. Maximum blood concentrations (at 0.5 hr) were 2-3 ug/mL, declining by 50% 1 hr after dosing.
Twelve metabolites of pirimiphos-methyl were separated by thin-layer chromatography from the urine of rats & a dog. No unchanged compound was detected & no metabolite had anticholinesterase activity. Briefly, the P-O bond is cleaved extensively & N-dealkylation &/or conjugation is a further step in the metabolism of the pyrimidine leaving group.
The mechanism by which large repeated doses of pirimiphos-methyl reduces the hemoglobin of rats is unknown. It may be caused by 2-diethylamino-4-hydroxy-6-methylpyrimidine, a metabolite formed by both mammals and plants. Although this metabolite has an acute toxicity of the same order of magnitude as the parent compound, it was (unlike the parent compound) tolerated by rats at a dosage of 400 mg/kg for 2 wk; even so, its action on the blood was indicated by an incr in reticulocytes & a decr in lymphocytes.
Metabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
読み込み中…
29232-93-7DTXSID0024266CHEMBL1886047CHEBI:388430.000015 [mmHg]
2 mPa (1.50X10-5 mg Hg) at 20 °C; 6.9 mPa (5.17X10-5 mm Hg)) at 30 °C
1.5x10-5 mmHg
Pirimiphos-methyl is a yellow liquid. Corrosive to tin and mild steel. Used as an insecticide.
Straw colored liquid; mp = 15-18 deg C (technical grade); [HSDB]
Yellow or straw-colored liquid.
化学的特性Light yellow, straw colored, or amber oily liquid. Odorless when pure.
USEPA/Office of Prevention, Pesticides and Toxic Substances; Interim Reregistration Eligibility Decision (IRED) for Pirimiphos-methyl (June 2001). EPA issues an IRED for a pesticide that is undergoing reregistration, requires a reregistration eligibility decision, and also needs a cumulative assessment under FQPA. The IRED, issued after EPA completes the individual pesticide's aggregate risk assessment, may include taking risk reduction measures -- for example, reducing risks to workers or eliminating uses that the registrant no longer wishes to maintain -- to gain the benefits of these changes before the final RED can be issued following the Agency's consideration of cumulative risks.[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]
USEPA/Office of Prevention, Pesticides and Toxic Substances; Reregistration Eligibility Decision Document - Pirimiphos-methyl (July 2006). The RED summarizes the risk assessment conclusions and outlines any risk reduction measures necessary for the pesticide to continue to be registered in the U.S.[Available from, as of October 11, 2012: http://iaspub.epa.gov/apex/pesticides/f?p=CHEMICALSEARCH:1]
Tolerances are established for residues of the insecticide pirimiphos-methyl (O-(2-diethylamino-6-methyl-4-pyrimidinyl) O,O-dimethyl phosphorothioate) in or on the following raw agricultural commodities:[Table#6553]
... EPA has completed its assessment of the cumulative risks from the organophosphate (OP) class of pesticides as required by the Food Quality Protection Act of 1996. In addition, the individual OPs have also been subject to review through the individual-chemical review process. The Agency's review of individual OPs has resulted in the issuance of Interim Reregistration Eligibility Decisions (IREDs) for 22 OPs /including pirimiphos-methyl/, interim Tolerance Reassessment and Risk Management Decisions (TREDs) for 8 OPs, and a Reregistration Eligibility Decision (RED) for one OP, malathion. These 31 OPs are listed in Appendix A. EPA has concluded, after completing its assessment of the cumulative risks associated with exposures to all of the OPs, that: (1) the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) are indeed eligible for reregistration; and (2) the pesticide tolerances covered by the IREDs and TREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) meet the safety standard under Section 408(b)(2) of the FFDCA. Thus, with regard to the OPs, EPA has fulfilled its obligations as to FFDCA tolerance reassessment and FIFRA reregistration, other than product-specific reregistration.
The Agency has completed its assessment of the occupational and ecological risks associated with the use of pesticides containing the active ingredient pirimiphos-methyl, as well as a pirimiphos-methyl-specific dietary risk assessment that has not considered the cumulative effects of organophosphates as a class. Based on a review of these data and public comments on the Agency's assessments for the active ingredient pirimiphos-methyl, EPA has sufficient information on the human health and ecological effects of pirimiphos-methyl to make an interim determination of reregistration eligibility and to make some interim decisions as part of the tolerance reassessment process under FFDCA and reregistration under FIFRA, as amended by FQPA. The Agency has determined that pirimiphos-methyl is eligible for reregistration provided that: (i) current data gaps and additional data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted, and label amendments are made to reflect these measures; and (iii) 16 the cumulative risk assessment for the organophosphates support a final reregistration eligibility decision. ... At the time that a cumulative assessment is conducted, the Agency will address any outstanding risk concerns. For pirimiphos-methyl, if all changes outlined in this document are incorporated into the labels, then all current risks will be mitigated. But, because this is an interim RED, the Agency may take further actions, if warranted, to finalize the reregistration eligibility decision for pirimiphos-methyl after assessing the cumulative risk of the organophosphate class. Such an incremental approach to the reregistration process is consistent with the Agency's goal of improving the transparency of the reregistration and tolerance reassessment processes. By evaluating each organophosphate in turn and identifying appropriate risk reduction measures, the Agency is addressing the risks from the organophosphates in as timely a manner as possible.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Pirimiphos-methyl is found on List B. Case No: 2535; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): O-[2-(Diethylamino)-6-methyl-4-pyrimidinyl] O,O-dimethyl phosphorothioate; Data Call-in (DCI) Date(s): 06/11/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Organophosphates are susceptible to formation of highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.
Acute Tox. 4 (100%)
Acute toxicity (ingestion) - category 4
Acute toxicity (Oral) - Category 4
Acute toxicity (Oral) - Category 4
Acute Tox. 4
Biological Exposure Indices (BEI) [ACGIH] - Acetylcholinesterase activity in red blood cells = 70% of individual's baseline; Butylcholinesterase activity in serum or plasma = 60% of individual's baseline; Sample at end of shift; [TLVs and BEIs]
Do not use or store near heat or open flame. /Actellic 5E Insecticide Low Odor Formulation/
Do not contaminate water, food or feed by storage or disposal. ... Store in a cool place and protect from freezing. If accidentally frozen, reconstitute by gently warming to room temperature and thoroughly mixing contents. Keep container closed when not in use. /Actellic 5E Insecticide Low Odor Formulation/
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.
Open dumping is prohibited. /Actellic 5E Insecticide Low Odor Formulation/
Pesticides are acutely toxic. Improper disposal of excess pesticide; spray mixture or rinsate is a violation of Federal law. If these wastes cannot be disposed of by use according to label instructions, contact your State Pesticide or Environmental Control Agency, or the Hazardous Waste representative at the nearest EPA Regional Office for guidance. /Actellic 5E Insecticide Low Odor Formulation/
Nonrefillable containers. Do not reuse or refill this container. Clean container promptly after emptying. /Actellic 5E Insecticide Low Odor Formulation/
For more Disposal Methods (Complete) data for PIRIMIPHOS-METHYL (8 total), please visit the HSDB record page.
Users should: Wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet; Remove clothing/PPE immediately if pesticides get inside. Then wash thoroughly and put on clean clothing; Remove PPE immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Actellic 5E Insecticide Low Odor Formulation/
Avoid contact with skin or clothing. Wash thoroughly with soap and water after handling. Remove contaminated clothing and wash clothing before reuse. /Actellic 5E Insecticide Low Odor Formulation/
Follow manufacturer's instructions for cleaning/maintaining PPE. If no such instructions for washables exist, use detergent and hot water. Keep and wash PPE separately from other laundry. Discard clothing and other absorbent material that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. /Actellic 5E Insecticide Low Odor Formulation/
Do not apply directly to water. /Actellic 5E Insecticide Low Odor Formulation/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]:
Mixers, loaders, and other handlers supporting admixture seed and/or grain treatments must: long sleeve shirt and long pants, shoes plus socks, chemical-resistant gloves, protective eyewear. /Actellic 5E Insecticide Low Odor Formulation/
All other mixers, loaders, applicators and other handlers must wear: coveralls over long sleeve shirt and long pants; chemical-resistant footwear plus socks; chemical-resistant gloves; protective eyewear. In addition, mixers and loaders must wear: chemical-resistant apron. /Actellic 5E Insecticide Low Odor Formulation/
Skin decontamination ... In patients ... Attendants should wear rubber gloves as vinyl provides no protection against skin absorption. /Organophosphate pesticides/
If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.
The effect of L-ascorbic acid supplementation on Pirimiphos-methyl induced toxicity was studied in albino rats. Biochemical estimations were made in rats administered orally the insecticide at 100 and 200 mg/kg body weight with or without oral supplementation of L-ascorbic acid at 200 mg/kg b.w. The biochemical assessments included estimations of brain and plasma cholinesterases, levels of ascorbic acid in liver, kidney and adrenals, urinary levels of ascorbic acid and glucuronic acid. A lower degree of inhibition of the cholinesterases was evident in ascorbic acid supplemented rats. Marked elevation in urinary levels of ascorbic acid and glucuronic acid was observed in the insecticide treated rats. Results of this study suggests that L-ascorbic acid supplementation partially offsets Pirimiphos-methyl induced toxicity
Technical hexachlorocyclohexane (100 mg/kg/d) and pirimiphosmethyl EC 50 (250 mg/kg/d) given individually and in combination to female rats for 7, 15 or 30 d by skin application caused poisoning, pathomorphological changes in vital organs, and significant enzymatic changes in liver and serum. The changes produced by the 2 compounds in combination did not suggest potentiation at the tested dose levels.
The pesticides benomyl, a benzimidazole fungicide, and pirimiphos-methyl, an organophosphorus insecticide, were tested separately and in combination at a ratio of 6:1, a mixture frequently found in foodstuffs by residual analysis, to determine their possible genotoxic action. The effect was measured by the micronucleus test carried out on cultured rat hepatocytes stimulated to proliferate by epidermal growth factor (EGF). Adult rat hepatocytes were exposed in vitro for 48 hr to the substances at increasing non-cytotoxic doses, chosen on the basis of cytotoxicity tests such as LDH and Neutral red assays. Benomyl induced a significant dose-related increase in micronucleus frequency; in contrast, pirimiphos-methyl was not genotoxic at any dose tested. When the hepatocytes were exposed to the two pesticides together at increasing doses, an enhancement in micronucleus frequency similar to that of benomyl alone was found, indicating that at this ratio and non-cytotoxic doses (up to 25 micrograms/mL benomyl + 4.2 micrograms/mL pirimiphos-methyl) no interaction occurs.
Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.
LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 11 days; diet 298 ppm for 8 days (95% confidence interval: 163-650 ppm)
LC50; Species: Colinus virginianus (Northern Bobwhite Quail) age 14 days; diet 207 ppm for 8 days (95% confidence interval: 106-407 ppm)
LC50; Species: Anas platyrhynchos (Mallard Duck) age 14 days; diet 633 ppm for 8 days (95% confidence interval: 453-883 ppm)
LD50; Species: Colinus virginianus (Northern Bobwhite Quail) age 1 yr; percutaneous 56.6 mg/kg bw for 24 days
For more Ecotoxicity Values (Complete) data for PIRIMIPHOS-METHYL (33 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), reported Koc values of 950 to 8500(2) indicate that pirimiphos-methyl is expected to have low to no mobility in soil(SRC). Volatilization of pirimiphos-methyl from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 6.0X10-7 atm-cu m/mole(SRC), based upon its vapor pressure, 1.5X10-5 mm Hg(2), and water solubility, 10 mg/L(2). Pirimiphos-methyl is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(2). Pirimiphos-methyl had a dissipation half-life of 5.2 to 5.9 days in soil(3). Calculated hydrolysis half-lives of 7.3 days at pH 5, 79.0 days at pH 7, and 54.0-62.0 days at pH 9(4) suggest that hydrolysis in moist soil may be an important environmental fate process(SRC).
AQUATIC FATE: Based on a classification scheme(1), reported Koc values of 950 to 8500(2) indicate that pirimiphos-methyl is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 6.0X10-7 atm-cu m/mole(SRC), derived from its vapor pressure, 1.5X10-5 mm Hg(2), and water solubility, 10 mg/L(2). According to a classification scheme(4), an estimated BCF of 270(SRC), from its log Kow of 4.12(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Calculated hydrolysis half-lives for pirimiphos-methyl are 7.3 days at pH 5, 79.0 days at pH 7, and 54.0-62.0 days at pH 9(6).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pirimiphos-methyl, which has a vapor pressure of 1.5X10-5 mm Hg at 20 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase pirimiphos-methyl 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 2.4 hours(SRC), calculated from its rate constant of 1.6X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase pirimiphos-methyl may be removed from the air by wet or dry deposition(SRC). Pirimiphos-methyl contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
In a 1995 monitoring program in Egypt pirimiphos-methyl was not detected in cabbage, cauliflower, carrot, courgette, cucumber, eggplant, green beans, green peas, lettuce, onion, pepper, apple, cantaloupe, grape, guava, mango, peach or strawberry samples(1). Pirimiphos-methyl was detected in 1 of 62 tomato samples at 0.06 mg/kg in the same 1995 monitoring program(1). In a 1996 monitoring program in Egypt pirimiphos-methyl was not detected in cabbage, lettuce, melokhia, spinach, watercress, artichoke, broad bean, cauliflower, cantaloupe, eggplant, green peas, okra, onion, squash, tomato, sweet potato, taro, apple, aqricot, banana, dates, fig, grape, quava, lemon lime, mango, peach, pear, plum or strawberry(2). Pirimiphos-methyl was detected in 1 of 24 grape leaf, 2 of 94 cucumber, 1 of 161 green beans, 7 of 91 pepper, and 1 of 42 carrot samples at 0.02, 0.07, 0.03, 0.39, and 0.08 mg/kg, respectively, in the same 1996 monitoring program(2). Pirimiphos-methyl was not detected (detection limit 0.015 mg/kg) in 130 commercial egg samples taken from Sao Paulo City, Brazil from Oct 2003 to July 2005(3). Pirimiphos-methyl was detected in 7 of 2223 fruit and vegetable samples at 0.05 to 0.10 mg/kg (positive detections were in green bean, guava, strawberry, spice, sweet pepper), samples were collected from Brazilian Sao Paulo General Storage and Wholesale over the period of Jan 1994 to Dec 2001(4). A market basket survey of produce conducted in Trinidad, West Indies from Oct 1996 to May 1997 reported that pirimiphos-methyl was not detected in sweet pepper, cabbage, lettuce, cauliflower, celery, Pak-choi, cucumber, spinach, chive tomato, hot pepper, cilantro, okra, watercress, eggplant, sorrel fruit or green beans(5). Pirimiphos-methyl was not detected (detection limit 25 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants, sampling took place Oct 2004, Jan and May 2005(6).
Pirimiphos-methyl was not detected (detection limit 25 ug/kg) in 298 raw milk samples obtained directly from tank trucks during delivery at nine Italian dairy plants, sampling took place Oct 2004, Jan and May 2005(1).
/EXPERIMENTAL/ In cows ... during the first 3 days 0.35% of the label was excreted in milk. The milk contained 0.04 ppm of pirimiphos-methyl equivalents, of which <2% was unchanged compound & phosphorus metabolites.
Pirimiphos-methyl is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.
As part of FDA Total Diet Study between 1984-1986, between the years 1984-1986, the mean daily intake per unit body weight (ug/kg body wt/day) of pirimiphos-methyl was measured for the following age groups: 6-11 mo (0.0014), 2 yr (0.0041), 14-16 yr female (0.0015), 14-16 yr male (0.0018), 25-30 yr female (0.0016), 25-30 yr male (0.0014), 60-65 yr female (0.0006), and 60-65 yr male (0.0007)(1). In Belgium, the average daily intake of pirimiphos-methyl was 0.03 mg/kg/day(2).
/AQUATIC SPECIES/ The acute toxicity of Pirimiphos-methyl (Actellic) was investigated using Guppy (Poecilia reticulata) in a 96 hr static renewal laboratory bioassay. Based on probit analysis the LC50 was 0.026, 0.024, 0.022 and 0.019 ml/L at 24, 48, 72 and 96 hr, respectively. Analysis of Variance (ANOVA) showed that there was significant difference (p < 0.05) in the quantal response (mortality) of P. reticulata to different concentrations of Actellic at 24, 48, 72 and 96 hr of exposure. Actellic insecticide is toxic to fish.
/AQUATIC SPECIES/ ... Evaluations were conducted in southeastern Queensland, Australia, to determine the toxicities of two organophosphate compounds (temephos and pirimiphos-methyl), an insect growth regulator (s-methoprene), and an entomopathogenic bacterium (Bacillus thuringiensis variety israelensis de Barjac ...) to Culex annulirostris ..., an Australian freshwater mosquito vector of arboviruses, and to Caradina indistincta, ... a co-habiting nontarget shrimp species. S-methoprene and B.thuringiensis were safest for C. annulirostris control with lethal dose ratios (LC95 nontarget/LC95 target) of 3,300 and 846,000, respectively. In contrast, lethal dose ratios for temephos and pirimiphos-methyl were 0.05 and 0.00005, respectively, suggesting that they are environmentally unsuitable. Based on their high lethal dose ratios, s-methoprene and B. thuringiensis are recommended for control of larval C.annulirostris in Australian freshwater habitats.
Tolerances are established for residues of the insecticide pirimiphos-methyl (O-(2-diethylamino-6-methyl-4-pyrimidinyl) O,O-dimethyl phosphorothioate) in or on the following raw agricultural commodities:[Table#6553]
... EPA has completed its assessment of the cumulative risks from the organophosphate (OP) class of pesticides as required by the Food Quality Protection Act of 1996. In addition, the individual OPs have also been subject to review through the individual-chemical review process. The Agency's review of individual OPs has resulted in the issuance of Interim Reregistration Eligibility Decisions (IREDs) for 22 OPs /including pirimiphos-methyl/, interim Tolerance Reassessment and Risk Management Decisions (TREDs) for 8 OPs, and a Reregistration Eligibility Decision (RED) for one OP, malathion. These 31 OPs are listed in Appendix A. EPA has concluded, after completing its assessment of the cumulative risks associated with exposures to all of the OPs, that: (1) the pesticides covered by the IREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) are indeed eligible for reregistration; and (2) the pesticide tolerances covered by the IREDs and TREDs that were pending the results of the OP cumulative assessment (listed in Attachment A) meet the safety standard under Section 408(b)(2) of the FFDCA. Thus, with regard to the OPs, EPA has fulfilled its obligations as to FFDCA tolerance reassessment and FIFRA reregistration, other than product-specific reregistration.
The Agency has completed its assessment of the occupational and ecological risks associated with the use of pesticides containing the active ingredient pirimiphos-methyl, as well as a pirimiphos-methyl-specific dietary risk assessment that has not considered the cumulative effects of organophosphates as a class. Based on a review of these data and public comments on the Agency's assessments for the active ingredient pirimiphos-methyl, EPA has sufficient information on the human health and ecological effects of pirimiphos-methyl to make an interim determination of reregistration eligibility and to make some interim decisions as part of the tolerance reassessment process under FFDCA and reregistration under FIFRA, as amended by FQPA. The Agency has determined that pirimiphos-methyl is eligible for reregistration provided that: (i) current data gaps and additional data needs are addressed; (ii) the risk mitigation measures outlined in this document are adopted, and label amendments are made to reflect these measures; and (iii) 16 the cumulative risk assessment for the organophosphates support a final reregistration eligibility decision. ... At the time that a cumulative assessment is conducted, the Agency will address any outstanding risk concerns. For pirimiphos-methyl, if all changes outlined in this document are incorporated into the labels, then all current risks will be mitigated. But, because this is an interim RED, the Agency may take further actions, if warranted, to finalize the reregistration eligibility decision for pirimiphos-methyl after assessing the cumulative risk of the organophosphate class. Such an incremental approach to the reregistration process is consistent with the Agency's goal of improving the transparency of the reregistration and tolerance reassessment processes. By evaluating each organophosphate in turn and identifying appropriate risk reduction measures, the Agency is addressing the risks from the organophosphates in as timely a manner as possible.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their continued use. Under this pesticide reregistration program, EPA examines newer health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether the use of the pesticide does not pose unreasonable risk in accordance to newer saftey standards, such as those described in the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern than those on List C, and with List C containing pesticides of greater concern than those on List D. Pirimiphos-methyl is found on List B. Case No: 2535; Pesticide type: insecticide; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.; Active ingredient (AI): O-[2-(Diethylamino)-6-methyl-4-pyrimidinyl] O,O-dimethyl phosphorothioate; Data Call-in (DCI) Date(s): 06/11/91, 10/13/95; AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Pirimiphos-methyl is known to be absorbed through intact skin, from the GI tract, & by inhalation.
Oral administration of 2-(14)C-ring-labelled pirimiphos-methyl at a dose of 0.6 mg/kg bw to five male rats resulted in a mean urinary excretion of 80.7% and mean fecal excretion of 7.3% in 24 hr, indicating rapid absorption. At 96 h, 86.0% and 15.2% of the administered dose had been excreted in urine and feces, respectively. Nine (unidentified) metabolites were present in the urine.
Female rats given 2-(14)C-pirimiphos-methyl at a dose of 7.5 mg/kg bw orally were bled (cardiac puncture, three rats per time interval) at 0.5, 1, 3, 5, 7 or 24 hr after dosing. Maximum blood concentrations (at 0.5 hr) were 2-3 ug/mL, declining by 50% 1 hr after dosing. By 24 hr, concentrations of (14)C in blood were 0.2-0.3 ug/mL, and of pirimiphos-methyl, 0.01-0.02 ug/mL. Rats treated for 4 days with 2-(14)C-pirimiphos-methyl at a dose of 7.5 mg/kg bw per day and sacrificed at intervals of 24 hr did not show any increase in blood concentrations with time. Tissue concentrations of total radioactivity in the liver, kidney and fat over the 4 days were generally less than 2 mg pirimiphos-methyl equivalents/kg tissue (concentrations of unchanged pirimiphos-methyl being less than 0.15 mg/kg tissue). There was no evidence of tissue accumulation.
Adult male Wistar rats were intubated with (14)C-labelled pirimiphos-methyl at a dose of 1 mg/kg bw per day. Four groups of three animals were dosed for 3, 7, 14 or 21 days and sacrificed 24 hr after the final dose. A further five groups of three rats were given similar doses for 28 days and sacrificed 1, 3, 7, 14, or 28 days after dosing. For each of the nine groups, one rat that did not receive pirimiphos-methyl was used as a control. After sacrifice, samples of liver, kidney, muscle, fat, erythrocytes and plasma were taken for analyses. Urine and feces were collected from two rats during the 24 hr after the seventh dose. Recovery of (14)C from (14)C-labelled pirimiphos-methyl added to control tissues was 96.9 +/- 5.2%. In all tissue samples taken at all time intervals, the concentration of radioactivity was very low, close to or below detection limits. Concentrations did not increase with repeated dosing. Liver concentrations were fairly constant (0.03 ppm) and similar concentrations were detected in some kidney samples. In other tissues, the concentration of radioactivity was generally below the limits of detection (0.04-0.06 ppm). Three days after cessation of dosing, one animal had detectable concentrations of radioactivity in the kidney. At 7 days and on subsequent days, no residues were found. Excretion was between 70% and 80% of a single dose, after administration of seven consecutive doses, providing evidence for rapid metabolism and elimination rather than poor absorption.
For more Absorption, Distribution and Excretion (Complete) data for PIRIMIPHOS-METHYL (6 total), please visit the HSDB record page.
Used as insecticide and veterinary ectoparasiticide; [Merck Index] Used to control insects and mites in vegetables, warehouses, stored grain, animal housings, and domestic and industrial areas; [HSDB] Registered in the US as general use classification insecticide for sorghum and corn (seed and stored), cattle ear tags, and fogging iris bulbs; [Reference #1]
Farming (Pesticides) [Category: Industry]
For pirimiphos-methyl (USEPA/OPP Pesticide Code: 108102) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Control of a wide range of insects and mites in warehouses, stored grain, animal houses, domestic and industrial premises; chewing insects; sucking insect; boring insects; and mites on vegetables, ornamentals, bulb flowers, sugar cane, maize, sorghum, rice, citrus and other fruit, olives, vines, alfalfa, cereals, etc.; and glasshouse pests (especially Whitefly, Thrips, Mealybugs, Aphids and mites) on tomatoes, cucumbers, capsicums, aubergines and other glasshouse crops.
This is a man-made compound that is used as a pesticide.
USEPA/OPP Pesticide Code 108102; Trade Names: R-33986, PP 511, Actellic, Actellifog, Blex, Silosan, Pirimifosmethyl, ENT 27699GC.
Emulsifiable liquid concentrates at 57% a.i. Treated Articles (Ear Tags) at 14% and 20% a.i.
Dispersible powder, emulsifiable concentrate, ultralow-volume liquid, water-soluble powder, aerosol dispersion.
Smoke generate, hot fogging concentrate, cold fogging concentrate, solution for seed treatment, water soluble granules.
For more Formulations/Preparations (Complete) data for PIRIMIPHOS-METHYL (9 total), please visit the HSDB record page.
Acaricides, Insecticides
Environmental transformation -> Pesticides (parent, predecessor)
使用Pirimiphos-methyl is a phosphorothioate used as an insecticide. Pirimiphos-methyl is commonly used for mosquito control as well as control of greenhouse crop pests and stored-product insects.
一般的な説明Yellow liquid. Corrosive to tin and mild steel. Used as an insecticide.
定義ChEBI: An organic thiophosphate that is O,O-dimethyl O-pyrimidin-4-yl phosphorothioate substituted by a methyl group at position 6 and a diethylamino group at position 2.