HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyrinuron
PYRINURON · VACOR · Vacot · dlp787 · dlp-87 · rh-787 · lh 105 · pnu[qr]
Identifiers & Physical Properties
| CAS No. | 53558-25-1 |
|---|---|
| Molecular formula | C13H12N4O3 |
| Average molar mass | 272.26 g/mol |
| Monoisotopic mass | 272.09094024 g/mol |
| SMILES | O=C(NCc1cccnc1)Nc1ccc([N+](=O)[O-])cc1 |
| InChIKey | CLKZWXHKFXZIMA-UHFFFAOYSA-N |
| PubChem CID | 40813 |
| ChEMBL | CHEMBL1528242 |
| EC No. | 258-626-7 |
| DTXSID | DTXSID1042360 |
Chemical & Physical Properties
| XLogP | 1.2 |
|---|---|
| Topological polar surface area | 99.8 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 3 |
| Heavy atoms | 20 |
| Formal charge | 0 |
| Complexity | 337 |
| Pesticides | Pesticides -> Rodenticides |
| LogP (partition coefficient) | log Kow = 2.09 /Estimated/ |
| Color/Form | Yellow, resembles cornmeal or yellow-green powder |
| Solubility | In water, 4.81X10+2 mg/L at 25 °C /Estimated/>40.8 [ug/mL] (The mean of the results at pH 7.4) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Melting point | Decomposes at 433 °F (EPA, 1998)223-225 °C (decomp)223-225° (dec) |
| Vapor pressure | 3.39X10-9 mm Hg at 25 °C /Estimated/0.00001 [mm Hg] @25 °C |
| Henry's law constant | Henry's Law constant = 1.84X10-16 atm-cu m/mol at 25 °C /Estimated/5.4×1010 mol/(m3Pa) at 25℃, HSDB (2015) |
| Physical Description | Pyriminil is a yellow, resembling corn meal. Used as a single-dose, acute rodenticide. Not registered as a pesticide in the U.S. (EPA, 1998)Yellow or yellow-green solid[HSDB] Light yellow flakes[MSDSonline] |
| Dissociation Constants | pKa1 = 3.5 (pyridine ring)pKa2 = 7.6 (benzyl amide) /Estimated/ |
| Collision Cross Section | 174.3 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID1042360] |
| Other Experimental Properties | Hydroxyl radical reaction rate constant = 1.11X10-11 cu cm/molecule-sec at 25 °C /Estimated/ |
| Boiling point | 415.32°C (rough estimate) |
| Density | 1.2545 (rough estimate) |
| Refractive index | 1.6120 (estimate) |
| pKa (acidity coefficient) | 12.25±0.46(Predicted) |
| CAS DataBase Reference | 53558-25-1 |
| FDA UNII | Q7BGS137YP |
| EPA Substance Registry System | Pyrinuron (53558-25-1) |
| GHS pictogram | GHS07,GHS05 |
| Signal word | Danger |
| GHS hazard statements | H318-H335-H302-H315 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P280-P305+P351+P338-P310 |
| UN transport number | 2588 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1(a) |
| Packing group | I |
| Hazardous substances data | 53558-25-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in male, female rats: 6.2, 7.2 mg/kg (Brooks, Htun) |
Safety & Regulations
| GHS classification | DangerH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.H300: Fatal if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatory information | The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.) |
| DOT label | Poison |
| Fire hazards | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Health hazards | This chemical may cause death by cardiovascular collapse and respiratory failure. It may cause diabetes. Also it affects the central nervous system. Human survivors regularly develop an insulin-deficient, ketosis-prone form of diabetes millitus. (EPA, 1998) |
| Hazards summary | Destroys pancreatic beta cellsIn human poisoning cases after ingestion, caused orthostatic hypotension, autonomic dysfunction, encephalopathy, peripheral neuropathy, hyperglycemia, and ketoacidosisSystemic poisoning not reported after inhalation or skin absorptionA dose as low as 19 grams may be fatal[HSDB] Humans who survive poisoning have developed insulin-dependent diabetes mellitus[CAMEO] |
| Reactive group | Amides and Imides |
| Reactivity Profile | An organic compound with a nitroaromatic component as well as a pyridine ring and an amide linker. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| CERCLA reportable quantities | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Pyriminil is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 100 or 10,000 lbs. Extremely hazardous substances that are solids are subject to either of two threshold planning quantities ... The lower quantity applies only if the solid exists in powdered form and has a particle size less than 100 micronsor is handled in solution or in molten formor meets the criteria for a National Fire Protection Association (NFPA) rating of 2, 3 or 4 for reactivity. If the solid does not meet any of these criteria, it is subject to the upper ... threshold planning quantity ... . |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (Oral) - Category 1 |
| Fire fighting | This compound is a solid pesticide. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. |
| First aid | Warning: Acute ingestion of pyriminil may result in development of insulin-deficient, ketosis-prone diabetes millitus. |
| Nonfire spill response | This compound is a solid pesticide. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Ventilate closed spaces before entering them. Remove and isolate contaminated clothing at the site. Do not touch spilled materialstop leak if you can do so without risk. Use water spray to reduce vapors. |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]: |
| Protective Action Criteria (PAC) | 0.52 [mg/m3]5.8 [mg/m3]35 [mg/m3] |
| Personal Protective Equipment (PPE) | For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998) |
| Interactions | Whatever microsomal enzymes are responsible for metabolism of pyriminil are induced by pretreatment with 3-methylcholanthrene, which increases biliary excretion of the metabolites and decreases pyriminil toxicity 50-fold.... The antidotal efficacy of nicotinamide (p.o. or i.p.) was greatest when administered within 1 hr of Vacor, or when pre-fed in diet. Nicotinic acid was less effective. Rats fed high levels of L-tryptophan or acutely pretreated were protected against Vacor, while D-tryp. and other amino acids were less effective. Agents such as atropine, PAM or nikethamide delayed but did not prevent death. Vacor or 2,4-DNP caused similar symptoms, suggesting interference with mitochondrial respiration. While mild Vacor-induced hyperglycemia was seen in rats and reversed by insulin, its role in ultimate toxicity is unclear. Vacor biotransformation appears to be more significant in detoxication, but prior bioactivation was not necessarily excluded. Cyt. P-448 induction by 3-MC pretreatment decreased Vacor toxicity 50-fold, while other classes of MFO inducers (PB, DMSO, PCN) did not significantly alter its potency. Reduction of P-450 complex activity by starvation or CS2 pretreatment potentiated the toxicity, but SKF-525A delayed death. Pretreatment with diethyl maleate, cobaltous chloride, or neomycin did not significantly alter Vacor toxicity. |
| Ecotoxicity values | LC50 Cyprinus carpio >100 mg/L/48 hr /Conditions of bioassay not specified in source examined/ |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,990(SRC), determined from a structure estimation method(2), indicates that pyriminil is expected to have low mobility in soil(SRC). Volatilization of pyriminil from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.84X10-16 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Pyriminil is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.39X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data are not available for pyriminil(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,990(SRC), determined from a structure estimation method(2), indicates that pyriminil 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 1.84X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa values of pyriminil are 3.5 for the conjugate acid of the pyriding ring nitrogen and 7.6 for the benzyl amide acting as an acid(5). The pKa of 3.5 indicates that the pyridine nitrogen will not be ionized at environmental pHs(6). However, the pKa of 7.6 indicates that the benzyl amide group will partially exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 8(SRC), from an estimated log Kow of 2.09(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data are not available for pyriminil(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), pyriminil, which has an estimated vapor pressure of 3.39X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase pyriminil may be removed from the air by wet and dry deposition(SRC). |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Ecotoxicity excerpts | /BIRDS and MAMMALS/ The toxicity of the rodenticidal product Pyriminyl (Vacor) was tested in 4 dogs, 9 cats, 11 coypus, and 16 ducks . In the tested dogs the 1000mg dose per kg l. w. was lethal only in 17% of cases. The results demonstrate that the LD50 for the dog is higher than stated in the literature (1000 mg/kg l. w.). Dogs show a high variability in their sensitivity to the product, since some of them died at lower doses. It can be assumed that 1 to 2% field bait will not induce any lethal intoxication in dogs. Doses of 300 mg/kg l. w. and higher were lethal for cats. The dose of 200 mg/kg killed 66% of the cats tested. There is a high possibility of poisoning cats in field deratization campaigns with Vacor. Coypus show clinical symptoms of intoxication after ingesting a Vacor bait at a 100 mg dose per kg l. w.however, they remain alive. Doses of 300 mg/kg l.w. and higher kill all the animals tested. The high sensitivity of coypus to Vacor suggests that Cpypus can be poisoned during Vacor deratization of coypus farms. Ducks were highly resistant to Vacor. Doses from 710 to 3000 mg per kg l. w. were endured without clinical changes, and the same was the case when the birds were given a diet with 2% concentration of Vacor for six days. The toxicological examination demonstrated the different amounts of Vacor in liver for different periods of time from the ingestion of the toxic agent, including the dependence on the animal species. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc for pyriminil can be estimated to be 1,990(SRC). According to a classification scheme(2), this estimated Koc value suggests that pyriminil is expected to have low mobility in soil. The estimated pKa values of pyriminil are 3.5 for the conjugate acid of the pyriding ring nitrogen and 7.6 for the benzyl amide acting as an acid(3). The pKa of 3.5 indicates that the pyridine nitrogen will not be ionized at environmental pHs(4). However, the pKa of 7.6 indicates that the benzyl amide group will partially exist in anion form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(4). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Accidental ingestion of pyriminil by a 25-mo-old boy resulted in acute vomiting, lethargy, seizures, hypoglycemia (followed by hyperglycemia and glucose intolerance), and autonomic and peripheral neuropathy./SIGNS AND SYMPTOMS/ ... involvement of the eyes ... has been limited to miosis with asymmetrical & sluggishly reactive pupils, sometimes ptosis of the lids, & occasionally nystagmus. In one extraordinary case a patient was found to have homonymous hemianopia, presumably from occipital infarct after intestinal perforation, hemorrhaging, & emergency surgery. This patient, like most patients with Vacor poisoning, had low blood pressure with persistent severe disabling orthostatic hypotension./SIGNS AND SYMPTOMS/ Clinical findings. The principal manifestations of poisoning with vacor are hypotension & hyperglycemia. Symptoms & signs: (From ingestion.) ... diffuse abdominal pain, lightheadedness, chest pain, weakness, blurred vision, polyuria, thirst, numbness of legs, lethargy, ataxia ... tremor, muscle cramps, sluggish pupillary responses, areflexia, loss of muscle stretch reflexes, dysphagia, postural hypotension ... bladder atony, impaired intellect, disturbances of balance, & delirium or stupor. B. Lab findings: The ECG shows ischemic changes in the myocardium. Blood analysis reveals hyperglycemia & hyponatremia. Ketotic acidosis may be present./SIGNS AND SYMPTOMS/ Other manifestations of the autonomic neuropathy include ... impotence, urinary retention, & constipation or diarrhea. A distal motor & sensory peripheral ... /nervous system disease/ was reported after PNU /N-3-pyridylmethyl-N-p-nitrophenylurea/ exposureit began within 1 day of ingestion & persisted with ataxia. A metabolic encephalopathy without seizure activity occurred after PNU (Vacor) ingestion. Decreased gastrointestinal motility may result in nausea, vomiting, & an ileus. A peanut odor may aid the diagnosis of PNU poisoning.For more Human Toxicity Excerpts (Complete) data for PYRIMINIL (12 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Pyriminil's former production and use as a rodenticide(1) may have resulted in its direct release to the environment(SRC). |
| Environmental Bioconcentration | An estimated BCF of 8 was calculated for pyriminil(SRC), using an estimated log Kow of 2.09(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). |
| Volatilization from Water/Soil | The Henry's Law constant for pyriminil is estimated as 1.84X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that pyriminil is expected to be essentially nonvolatile from moist soil or water surfaces(2). Pyriminil is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.39X10-9 mm Hg(SRC), determined from a fragment constant method(3). |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Acute Exposure/ Signs & symptoms of intoxication in dogs ... include abdominal pain, nausea & vomiting, central nervous depression, visual disturbances, anorexia, painful paresthesias, autonomic nervous system dysfunction with dystonia, & orthostatic hypotension. Ataxia, hyporeflexia, tremors & muscular weakness develop later. Death may be delayed for several days./LABORATORY ANIMALS: Acute Exposure/ ...Single dose of 1 mg produced signs of paralysis in rats./LABORATORY ANIMALS: Acute Exposure/ ... however, these same animals showed increased hexobarbital sleeping times & other evidence of inhibition of certain liver microsomal enzymes, especially p-nitro-anisole O-demethylase./LABORATORY ANIMALS: Acute Exposure/ ... in an animal model, the Dutch Belted rabbit. The electroretinogram b wave was especially susceptible to the effects of the rodenticide, and the target tissue appeared to be the retinal pigment epithelium. Injection of PNU itself did not produce ocular toxicity. The poison had to be administered orally. Gentamicin administered orally with PNU prevented the ocular toxicity. Presumably this antibiotic killed those gastrointestinal bacteria responsible for PNU's metabolism into an ocular toxin. L-tryptophan, a known antidote for the lethal effects of PNU, was an antidote for the ocular toxicity when administered orally but not when administered parenterally.For more Non-Human Toxicity Excerpts (Complete) data for PYRIMINIL (14 total), please visit the HSDB record page. |
| Environmental Abiotic Degradation | The rate constant for the vapor-phase reaction of pyriminil with photochemically-produced hydroxyl radicals has been estimated as 1.11X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3.5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Pyriminil is not expected to undergo hydrolysis in the environment due to the lack of functional groups that will hydrolyze under environmental conditions(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm). |
| TSCA inventory status | TSCA listed |
| UN transport number | 2588 |
| Toxicity | LD50 orally in male, female rats: 6.2, 7.2 mg/kg (Brooks, Htun) |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS05 |
| Hazard class | 6.1(a) |
| Packing group | I |
| GHS hazard statements | H318-H335-H302-H315 |
| GHS precautionary statements | P264-P270-P301+P312-P330-P501-P264-P280-P302+P352-P321-P332+P313-P362-P280-P305+P351+P338-P310 |
| Hazardous substances data | 53558-25-1(Hazardous Substances Data) |
Applications & Uses
Description
Pyriminil was used formerly as a rodenticide in products such as DLP 787 as a 10% house mouse tracking powder or Vacor. It is now banned in the United States and Europe for use as a rodenticide and is listed as an extremely hazardous substance by the US Environmental Protection Agency (EPA). Toxic effects of pyriminil include neurotoxicity and pancreatic beta-cell death, which, if not immediately lethal, will lead to prolonged autonomic dysfunction and permanent insulin-dependent diabetes mellitus in most species, including humans.
Uses
Pyriminil was used as a rodenticide in the United States to control rats and house mice since the 1920s. It is especially effective against rodents resistant to anticoagulant poisons. Pyriminil was marketed for indoor use only in the form of bait and tracking powder. However, commercial distribution was voluntarily withdrawn in 1975 in the United States after many severe human poisonings and suicides. In contrast, pyriminil was introduced to British market much later (in 1980).
Uses
Rodenticide.
General Description
Yellow, resembling corn meal. Used as a single-dose, acute rodenticide. Not registered as a pesticide in the U.S.