2-クロロ-4-ジメチルアミノ-6-メチルピリミジン

Rodenticides

Active substance -> EU Pesticides database: Not approved

Pesticides -> Rodenticides

Very soluble in ethanol

In water, 9.4 g/L at 20 °C

Readily soluble in dichloromethane, 2-propanol, toluene

Soluble in most common organic solvents, eg acetone, benzene, chloroform, diethyl ether, ethanol. Soluble in dilute acids.

284 to 297 °F at 4 mmHg (EPA, 1998)

140-147 °C at 4 mm Hg

189 °F (EPA, 1998)

87 °C

Brown waxy solid; mp: 87 °C /commercial crimidine/

MP: 218 °C /Crimidine hydrochloride/

MP: 146 °C /Crimidine picrate/

87 °C

Less than 10-5 at 68F (EPA, 1998)

0.02 [mmHg]

Crimidine appears as brown waxy solid or colorless crystals. Used as a rodenticide. Not registered as a pesticide in the U.S. (EPA, 1998)

Colorless solid; Commercial product is brown and waxy; [HSDB] Colorless odorless crystalline solid; [MSDSonline]

Positive

3.92

2.7

Agilent XCT

Electrospray ionization

formic acid (5.3nM)

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P264, P270, P301+P316, P321, P330, P405, and P501 (click each P-code to see the statement)

A pyridoxine antagonist that causes convulsions 20-40 minutes after ingestion of less than 5 mg/kg or less than 7 drops; A skin, eye, nose, and throat irritant; May cause burns to skin and eyes; [HSDB] May cause serious damage to CNS; [CAMEO] An irritant; May cause serious eye injury; May cause skin sensitization; Effects in high-dose animal studies include convulsions; [MSDSonline]

Anon; Crimidine; In: EPA Chemical Profiles, USEPA, Washington DC 20460, USA, 3p. Dec (1985). Aspects covered in this data sheet: chemical identity; exposure limits; physicochemical properties; fire and explosion hazards; reactivity; health hazards; uses; handling of spills or releases.

CRIMIDINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

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. Crimidine 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 microns; or is handled in solution or in molten form; or 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 ... .

Acute Tox. 1 (100%)

Acute toxicity - category 2

Acute Tox. 2 *

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.

This chemical is a noncombustible solid. Use dry chemical, carbon dioxide, water spray, or alcohol foam extinguishers. Poisonous gases are produced in fire including chloride fumes and nitrogen oxides. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position...

Spill Handling: Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Use organic vapor respiratory protection. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Do not touch spilled material; stop leak if you can do so without risk. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Small dry spills: with clean shovel place material into clean, dry container and cover; move containers from spill area. Large spills: dike far ahead of spill for later disposal. If water pollution occurs, notify appropriate authorities. Ventilate area of spill or leak. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters...

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.

Quickly remove contaminated clothing. Immediately wash area with large amounts of water. Seek medical attention immediately.

0.0038 [mg/m3]

0.041 [mg/m3]

0.25 [mg/m3]

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)

Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work.

Where the potential exists for exposure to Castrix, use a NIOSH approved full facepiece respirator with a pesticide cartridge. Increased protection is obtained from full facepiece air purifying respirators. If while wearing a filter, cartridge or canister respirator, you can smell, taste, or otherwise detect Castrix, or in the case of a full facepiece respirator you experience eye irritation, leave the area immediately. Check to make sure the respirator-to-face seal is still good. If it is, replace the filter, cartridge, or canister. If the seal is no longer good, you may need a new respirator. Where the potential for high exposures exists, use a NIOSH approved supplied-air respirator with a full facepiece operated in the positive pressure mode or with a full facepiece, hood, or helmet in the continuous flow mode, or use a NIOSH approved self-contained breathing apparatus with a full facepiece operated in pressure-demand or other positive pressure mode.

Be sure to use respiratory protection when /mixing/.

Pyridoxine was found to be an excellent antidote for mice poisoned with crimidine.

Subtoxic doses of 4-deoxopyridoxine and semicarbazide also had a protective effect; isonicotinylhydrazine, caffeine, and acetazolamide were partially effective in preventing convulsions due to Castrix.

LD50 Quail oral about 20 mg/kg (about 30 grains)

LC50 Goldfish > 500 mg/l/96 hr (pellets, 0.5%) /Conditions of bioassay not specified/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that crimidine is expected to have very high mobility in soil(SRC). Volatilization of crimidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-8 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Crimidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.023 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2006).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 22(SRC), determined from a structure estimation method(2), indicates that crimidine is not 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 3.8X10-8 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 2 from an estimated log Kow of 1.31(6), and a regression derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), crimidine, which has an estimated vapor pressure of 0.023 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in vapor phase in the ambient atmosphere. Vapor-phase crimidine 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 5 hours(SRC), calculated from its rate constant of 8.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).

/BIRDS and MAMMALS/ Crimidine is not a culmulative poison, but is rapidly metabolized. Birds are not harmed by the ingestion of a few grains of the formulation.

/AQUATIC SPECIES/ The accumulation of crimidine in total samples and in some organs of 5 fish species was studied under experimental conditions. The species were Cyprinus carpio, Carassius carassius, Tinca tinca, Scardinius erythrophthalamus, and Leucaspius delineatus. Fish were exposed to concn of 10 and 50 mg/L. During short-term expt, water and fish samples were taken at intervals of 6, 12, 24, 48, and 72 hr; during the long-term expt, sampling was performed weekly for 6 wk. Total samples were analyzed for Carassius carassius, Tinca tinca, Scardinius erythrophthalamus, and Leucaspius delineatus. Samples of individual organs and tissues were taken as follows: Cyprinus carpio-gills, digestive tract, muscular tissue, kidneys, gonads; Carassius carassius-gills, digestive tract, muscular tissue, ovaries, testes. Crimidine was determined by gas chromatog. The accumulation capacity of individual fish species did not differ greatly. Of the internal organs, only the kidneys had a high accumulation capacity; otherwise, the highest values were found in muscular tissue and the gills. After 1-3 wk, the amt of crimidine in most organs falls, and after transfer to clean water there is a general sharp decline. The authors concluded that crimidine is not firmly bound in the body.

/ACCIDENTAL POISONINGS/ In 12 of 714 stone martens (1.68%), post mortem examination revealed poisoned corn in the stomach and duodenum. All cases occurred in the winter from December-March. Male and female animals of different ages were affected. Morphologically, an extensive hyperemia was found in the skeletal muscles and in all organs. Toxicological examinations were made in 8 cases. In every case crimidine was established.

/FIELD STUDIES/ Crimidine is not a cumulative poison, but rapidly decomposes in the bodies of poisoned animals, which are therefore not toxic to predators.

Using a structure estimation method based on molecular connectivity indices(1), the Koc for crimidine can be estimated to be 22(SRC). According to a classification scheme(2), this estimated Koc value suggests that crimidine is expected to have very high mobility in soil(SRC).

/SIGNS AND SYMPTOMS/ Short Term Exposure: Contact can cause eye and skin irritation and burns. Inhalation can irritate the nose and throat. Exposure may result in serious central nervous system damage with anxiety, restlessness, muscle stiffness, light sensitivity, noise sensitivity, touch sensitive, cold sweat, and leading to convulsions that may be fatal. If patient survives 5 - 6 hours there may not be serious problems. Extremely toxic; ... probable oral lethal dose in humans is less than 5 mg/kg or less than 7 drops for a 70 kg (150 lb) person. Long Term Exposure: Chronic health effects are unknown at this time

/SIGNS AND SYMPTOMS/ Symptomatology (beginning 15 to 30 min after ingestion): 1. Without warning the patient may fall into a violent convulsion, but often prodromal symptoms are described, such as restlessness, apprehension, heightened acuity of perception (hearing, vision, feeling, etc), abrupt movements, hyperreflexia, and especially muscular stiffness of the face and legs. Rarely vomiting occurs. 2. A minor sensory stimulus may suddenly trigger a violent generalized convulsion which lasts from 0.5 to 2 min. At first the movements are intermittent (clonic), but a spinal tetanic phase quickly intervenes. ... Because the muscles of respiration are involved in a sustained spasm, breathing ceases and deep cyanosis appears. Consciousness is retained during the convulsion ... . 3. Between convulsions, muscular relaxation is typically complete. ... Cold perspiration covers the skin. ... Sudden stimuli such as a noise or even a draft of air may precipitate another paroxysm. 4. ... Death from respiratory arrest. ... 5. Repeated convulsions may lead to lactic acidemia, hyperkalemia and dehydration. /Strychnine/

/SIGNS AND SYMPTOMS/ Crimidine (2 chloro, 4 methyl, 6 dimethyl amidopyrine) is a synthetic rodenticide which causes acute poisonings after oral ingestion in /humans/. Major toxic effects are consciousness disorders, hypertonic coma and convulsions. Toxic level in human is about 5 mg/kg. An intoxication case is reported. Five serums collected at different times were analyzed ... Serum levels varied from 368 micrograms/L for H0 to 64 micrograms/L for H10 and elimination of crimidine was linear in time.

An estimated BCF of 2 was calculated for crimidine(SRC), using an estimated log Kow of 1.31(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).

The Henry's Law constant for crimidine is estimated as 3.8X10-8 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that crimidine is expected to be essentially nonvolatile from water surfaces(2). Crimidine's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected(SRC). Crimidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 0.023 mm Hg(SRC), determined from a fragment constant method(3).

/LABORATORY ANIMALS: Acute Exposure/ Crimidine is a rapidly acting convulsant pyridoxine antagonist whose effects became apparent within 20-40 minutes and which effects all species similarly. However, convulsions rarely occur in poultry, the usual sign being ptosis and somolence. There are no age and sex differences in its action on species. Poisoned rats are not toxic to predators. The clinical signs observed in crimidine poisoned dogs include convulsions, salivation, restlessness, fright, and muscular trembling.

/LABORATORY ANIMALS: Acute Exposure/ Crimidine causes convulsions or paralysis, with respiratory disorders as severe as pulmonary edema.

/LABORATORY ANIMALS: Acute Exposure/ Gray rats (Rattus norvegicus) of the experimental group were allowed to observe for 2 hr the action of acute raticides on another group over wire fencing, then the fencing was removed and the experimental group was given the bait with the same poison. The observation decreased the bait intake and thereby increased the survival after exposure to 0.5% crimitox from 0.22 to 0.30, thus showing different degrees of avoidance reaction.

/OTHER TOXICITY INFORMATION/ Unrelated cases of lethal poisoning of cats, 2 pheasants, and 1 dog with castrix grains containing 0.15% crimidine revealed lung edema with focal hemorrhages in certain of the cases.

/OTHER TOXICITY INFORMATION/ Intravenous or intraperitoneal injection of 3-20 mg of castrix/kg was administered to cats and the effects were followed until the death occurred. A toxic-convulsive influence on the central nervous system was established. The electroencephalogram changes preceded the epileptogenic convulsions. The behavior and the electrophysiological examinations distinguish 3 basic phases of the castrix action: initial state of an increased paroxysmal activity, demonstrated by an electroencephalogram desynchronization and the appearance of single spikes and sharp waves; a phase of a generalized epileptic seizure; and an agonal period with blocking of the cerebral electrogenesis. Castrix causes an irreversible intracerebral disintegration. Castrix is a typical chemical convulsant.

The rate constant for the vapor-phase reaction of crimidine with photochemically-produced hydroxyl radicals has been estimated as 8.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 5 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Crimidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).

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. Crimidine 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 microns; or is handled in solution or in molten form; or 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 ... .

Crimidine is a rapidly acting convulsant pyridoxine antagonist ...

In an attempt to elucidate the mechanism of the convulsive action of Castrix, the effects of Castrix and its analogs on several enzymes, their convulsive effects in mice, and the influence of other compounds on the convulsive effects of Castrix were investigated. At high concentrations in vitro, Castrix inhibited the activities of mouse brain pyridoxal kinase, glutamic decarboxylase, and acetylcholinesterase. The activities of these enzymes were not significantly altered by Castrix in vivo. Several structural analogs of Castrix displayed similar convulsive activity in mice. The elimination of chlorine from Castrix changed the mode of convulsive action, and the convulsions in this case could not be prevented by administration of vitamin B6. Replacing the 4-dimethylamino group of Castrix with an amino group eliminated the convulsive action but gave a depressive action. The mechanism by which Castrix competes with vitamin B6 was not found, since other vitamin B6 antagonists (e.g., toxopyrimidine) protected against the convulsive action of Castrix. ...

Pyrimidinamine rodenticide

Used as rodenticide (rapidly induces convulsions); Likely discontinued for pesticide use worldwide; [HSDB]

Not registered with the EPA for use as pesticide in the US; [CAMEO] Banned in the EU for use as pesticide; [eChemPortal: ESIS]

Farming (Pesticides) [Category: Industry]

Rodenticide which acts by rapidly inducing convulsions. Control of mice and voles. /Former/

Active Ingredients Believed to be Obsolete or Discontinued for Use as Pesticides. Active Ingredient: Crimidine, CAS no 535-89-7 /table/.

Rodenticide (pyrimidinamine rodenticide)

Prepared from an appropriate 2,4-dihalopyrimidine and dimethylamine ... US patent 2,219,858 (1940 to Winthrop).

The condensation product of thiourea and ethyl 3-oxobutyrate is chlorinated and reacted with one equivalent of dimethylamine.

Castrix-Giftkorner: 0.1% impregnated wheat grain.

Technical contains about 20% of the non-rodenticidal 4-chloro-N,N,6-trimethylpyrimidin-2-ylamine.

Introduced in early 1940's by I.G. Farben Industrie as rat poison.

The technical product ... containing about 20% of the inactive 4-chloro-2-dimethylamino isomer.

Product discontinued by Bayer AG.

... It is not customary to combine with other preparations.