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Chlorazine

Chlorazine structure

Chlorazine 

structure
  • CAS No:

    580-48-3

  • Formula:

    C11H20ClN5

  • Chemical Name:

    Chlorazine

  • Synonyms:

    1,3,5-Triazine-2,4-diamine,6-chloro-N2,N2,N4,N4-tetraethyl-;s-Triazine,2-chloro-4,6-bis(diethylamino)-;1,3,5-Triazine-2,4-diamine,6-chloro-N,N,N′,N′-tetraethyl-;Geigy 444;6-Chloro-N2,N2,N4,N4-tetraethyl-1,3,5-triazine-2,4-diamine;G 444E;G 25,804;2,4-Bis(diethylamino)-6-chloro-s-triazine;Chlorazin;Chlorazine;2-Chloro-4,6-bis(diethylamino)-s-triazine;Geigy 444E;Geigy Herbicide 444E;NSC 56355;NSC 56840;2,4-Bis(diethylamino)-6-chloro-1,3,5-triazine

Description

Solid. Soluble in hydrocarbons, alcohols, ketones; insoluble in water.


The prototypical phenothiazine antipsychotic drug. Like the other drugs in this class chlorpromazine's antipsychotic actions are thought to be due to long-term adaptation by the brain to blocking DOPAMINE RECEPTORS. Chlorpromazine has several other actions and therapeutic uses, including as an antiemetic and in the treatment of intractable hiccup.

Chlorazine Basic Attributes

257.76

257.76

209-459-3

T60AV22R32

56840|56355

DTXSID6041765

CRYSTALS OR OILY LIQUID

Characteristics

45.2

2.21740

1.0956 g/cm3 @ Temp: 20 °C

27 °C

154-156 °C @ Press: 4.0 Torr

188.3ºC

1.564

> 10% in ligroin

Oral-Rat LD50: 850 mg/kg; Oral-Mouse LD50: 743 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

Safety Information

36/37/38

26-36/37/39

Warehouse ventilated, low temperature and dry

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.|Noncombustible containers should be crushed & buried under more than 40 cm of soil. /Herbicides/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Noncombustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

USDA/Forest Service: Pesticide Background Statements (1984) Agr Hdbk 633|Ghassemi M et al; Environmental Fate and Impacts of Major Forest Use Pesticides, EPA 68-02-3174

The use of personal protective equipment such as glasses, synthetic gloves & /NIOSH approved breathing apparatus/ ... is important. /Herbicides/

Extinguish fire using agent suitable for type of surrounding fire. ... Use water in flooding quantities as fog. Use "alcohol foam" ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticide (compounds and preparations), solid (insecticides, agricultural, not elsewhere classified, other than liquid)/|Avoid breathing dusts & fumes from burning material. Keep upwind. /Triazine pesticide, solid, not otherwise specified, (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/

Only clean clothing ... should be worn & clothing should be changed daily ... Adequate sanitary facilites & washing water should be provided for workers to wash before meals. Smoking & consumption of alcoholic drinks before & during the handling of herbicides should be forbidden. Contaminated clothing should be removed immediately & a hot bath taken if possible. Personal hygiene should be encouraged. /Herbicides/|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. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Triazine pesticide, solid, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/ Not elsewhere classified.|Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Triazine pesticide, solid, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/

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.

The major hazards encountered in the use and handling of chlorazine stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this crystalline (or oily liquid) substance may occur from its use an an herbicide. Effects from exposure may include shortness of breath, muscle spasms, ataxia, and anorexia. In activities and situations where over exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. While chlorazine does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving chlorazine extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Chlorazine may be shipped via air, rail, road, and water, in containers bearing the label "Poison" (for solids), or "Flammable liquid" (for liquid formulations). Chlorazine should be stored away from sparks, flames, or other sources of ignition. Small dry spills of chlorazine may be placed into a clean, dry, covered container for later disposal (liquid solutions are first absorbed in sand or other noncombustible absorbent). Large liquid spills should be diked far ahead to prevent chlorazine from entering water sources and sewers. Before implementing land disposal of chlorazine consult with regulatory agencies for guidance.

Toxicity

moderately toxic

ETHANOL (4 G/KG/DAY FOR 21 DAYS) HAD NO EFFECT ON HEPATIC MICROSOMAL CYTOCHROME P450 IN RATS & ALCOHOL DEHYDROGENASE REMAINED UNCHANGED. CHLORAZINE (20 MG/KG, INTRAPERITONEAL) ADMIN FOLLOWING ETHANOL TREATMENT (4 G/KG/DAY FOR 21 DAYS) DECREASED CYTOCHROME P450 AND ALCOHOL DEHYDROGENASE ACTIVITY IN RATS. THUS ETHANOL & CHLORAZINE INTERACT NOT ONLY AT THE LEVEL OF THE CENTRAL NERVOUS SYSTEM, BUT ALSO AT THE LEVEL OF THE LIVER.

LD50 Rat oral 850 mg/kg

Chlorazine was at one marketed as or reported to be herbicide, but at present it is of little commercial interest. Therefore, at some time in the past it may have been released to the environment via effluents at manufacturing sites and at points of application where it may have been employed as a herbicide(SRC).

TERRESTRIAL FATE: THE FIRST INDICATION OF THE CLEAVAGE OF ALKYL GROUPS IN SOIL CAME FROM EXPT DESIGNED TO STUDY THE REASON FOR THE PRONOUNCED LAG PHASE IN THE PHYTOTOXIC ACTION OF CHLORAZINE ... IN OATS ... THE SHARP INCR OF PHYTOTOXICITY SEVERAL MO AFTER APPLICATION ... MAY BE EXPLAINED BY SUCCESSIVE DEALKYLATIONS TRANSFORMING CHLORAZINE INTO TRIETAZINE & SIMAZINE ...|TERRESTRIAL FATE: If chlorazine is released to soil, it will be expected to exhibit low mobility based upon(3) a calculated Koc of 797 estimated(2,SRC) based upon water solubility(1). Adsorption of chlorazine to clay materials has been observed to vary strongly with pH and electrolyte concn of the system(4). It has been predicted that >95% of the chlorazine applied to soil under field conditions will be adsorbed onto clay materials in the soil based upon experimental results for adsorption onto illite, kaolinite, and montmorillonite(4). Therefore, chlorazine is not expected to leach to ground water(SRC). Chlorazine may be subject to slow degradation in soil which may be due to both chemical hydrolysis and biodegradation based upon limited data for chlorazine and other structurally related s-triazines. It will not be expected to volatilize from near surface soils or surfaces under normal environmental conditions. Chlorazine applied to soil under field conditions is reportedly decomposed by soil microorganisms over 40 days based upon the lack of inhibition in the growth of winter grains in non-sterile soil versus the inhibition observed in sterile-soil(5).|AQUATIC FATE: If released to water, chlorazine will not be expected to bioconcentrate in aquatic organisms, adsorb to sediment and suspended particulate matter, or to volatilize. The s-triazine ring of chlorazine is fairly resistant to microbial attack. Information concerning biodegradation in soil(1) indicates moderately rapid biodegradation of chlorazine may occur in natural waters. Chemical hydrolysis of chlorazine may be more important environmentally than biodegradation at low pH or when various catalysts are present. Chlorazine may be susceptible to direct photolysis(2) and hydrolysis(3) based upon data concerning other s-triazine herbicides.|ATMOSPHERIC FATE: If chlorazine is released to the atmosphere, it may be subject to gas-phase reaction with hydroxyl radicals. The rate constant for the vapor-phase reaction of chlorazine with photochemically produced hydroxyl radicals has been estimated to be 154.4 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 2.5 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1).|TERRESTRIAL FATE: THE LONG SOIL PERSISTENCE OF THESE CMPD DOES ... CREATE THE PROBLEM OF SOIL CARRY OVER, WHICH CAN DAMAGE SUCCEEDING CASH CROPS. THEREFORE EXTREME CAUTION MUST BE TAKEN IN THEIR APPLICATION ON CROPLAND TO AVOID SUCH INJURY TO FOLLOWING CROPS. /TRIAZINES/

Photodecomposition appears to be minimal on soils. /Triazine herbicides/|Most of the triazines are very stable in soil & dissipate slowly through chemical conversion to the hydroxy form ... /Triazines/|The rate constant for the vapor-phase reaction of chlorazine with photochemically produced hydroxyl radicals has been estimated to be 154.4 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 2.5 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). Chlorazine may be subject to slow hydrolysis in water or soil based upon the hydrolysis behavior of other s-triazine herbicides with similar structures (eg, the hydrolysis half-lives for simazine in aqueous buffer solutions at 25 °C at pH 5, 7, and 9 are 70, >200, and >200 days, respectively(6)). Infrared studies of interactions of s-triazines such as simazine with mineral surfaces indicate that adsorption is usually followed by protonation and hydrolysis(2). The rate of hydrolysis may be increased by various catalysts based upon the observed increase in rate of hydrolysis rates for the chemically similar herbicide atrazine in water solutions upon addition of sterilized soil(5) and humic(3) and fulvic acids(4). Chlorazine may be susceptible to photolysis based upon photolysis for s-triazines similar in structure to chlorazine such as simazine from experiments which utilized irradiation with artificial light at wavelenghts >290 nm(7).

Based upon a water solubility of 22 ppm at 26 degC(1), a BCF of 108 has been estimated(2). Based upon this estimated BCF, chlorazine will not be expected to bioconcentrate in aquatic organisms(SRC).

Adsorption of triazines through an exchange process to organic matter & clay minerals is dependent on the pH of the soln & the acidity of the adsorbent surface. Hydrogen bonding & hydrophobic bonding are other mechanisms by which soil organic matter adsorbs triazine herbicides, especially at higher pH levels. ... Transport from soil to water occurs in soln & in sediments. /Triazine herbicides/|Based upon a water solubility of 22 ppm at 26 °C(3), a Koc of 797 has been estimated(4). Based upon this estimated Koc, chlorazine will be expected to exhibit low mobility in soil(5). Evidence has been reported that indicates that the basicity of s-triazine herbicides, such as simazine, is not the main factor governing adsorption to soil humic acids(1). Adsorption of chlorazine to clay materials has been observed to vary strongly with pH and electrolyte concn of the system(6). It has been predicted that >95% of the chlorazine applied to soil under field conditions will be adsorbed onto clay materials in the soil based upon experimental results for adsorption onto illite, kaolinite, and montmorillonite(6). It has been shown that the ability of s-triazines herbicides to act as electron donors to electron acceptor quinone-like units of humic acids also plays an important role in the adsorption(2).

Vapor transport losses of triazines are dependent on vapor pressure & pH of the evaporating surface, since ionized cmpd are less volatile. /Triazine herbicides/|Based upon the Henry's Law constants calculated(SRC,2) from water solubility and vapor pressure for s-triazine herbicides with similar structures with chlorazine (eg, the Henry's Law constant is 4.63X10-10 atm-cu m/mole for simazine(1,SRC)), volatilization of chlorazine is not expected to be environmentally important(2).

Drug Information

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)|Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)|Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

In the metabolism of atrazine ... & other triazines, N-dealkylation of their cysteine & glutathione conjugation is usually observed, including oxidation of N-alkyl groups. /s-Triazines/

... Their chief mode of action appears to involve carbohydrate metabolism. The chlorinated s-triazines inhibit starch accumulation by blocking the production of sugars. Similar behavior has been shown for the methoxy & methylthio-s-triazines. It has been reported that the s-triazines affect the tricarboxylic acid cycle with activation of phospho-phenyl pyruvate-carboxylase causing the disappearance of sucrose & glyceric acid with the formation of aspartic & malic acids. /S-triazines/|SINCE CHLOROSIS IS THE FIRST SIGN OF THE EFFECT OF TRIAZINES ON PLANTS, INTERFERENCE WITH CARBON DIOXIDE ASSIMILATION & SUGAR FORMATION CAN BE EXPECTED. STUDIES SHOWING THAT HILL REACTION IS INHIBITED CONFIRMED THIS. /TRIAZINES/

Aminazine

Chlorazine Use and Manufacturing

Methods of Manufacturing

FORMERLY BY THE REACTION OF CYANURIC CHLORIDE WITH DIETHYLAMINE

Uses

Herbicide.

Production

(1972) NOT PRODUCED COMMERCIALLY IN USA|(1975) NOT PRODUCED COMMERCIALLY IN USA

PRODUCT DISCONTINUED BY CIBA-GEIGY CORPORATION.|NO LONGER PRODUCED COMMERCIALLY IN USA|PREPN: PEARLMAN, BANKS, J AM CHEM SOC 70: 3726 (1948); THURSTON ET AL, J AM CHEM SOC 73: 2981 (1951).|EFFECTIVE DOSE 50 (ED50) FOR CHLORAZINE IN WEEDS IS 0.31 PPM. SELECTIVITY INDEX: 0.38 (ED20 FOR CORN/ED80 FOR WEED).

THE RESULTS OF CHROMATOGRAPHIC ANALYSES OF S-TRIAZINE HERBICIDE RESIDUES WERE COMPARED. DETECTION LIMITS FOR THE 14 S-TRIAZINES WERE: 0.02-0.03 NG GAS CHROMATOGRAPHY/ALKALI FLAME IONIZATION, 0.8 NG IN GAS CHROMATOGRAPHY/FLAME IONIZATION DETECTION, 1 NG IN HIGH-PERFORMANCE LIQ CHROMATOGRAPHY (UV DETECTION), 3-5 NG IN HIGH PERFORMANCE THIN-LAYER CHROMATOGRAPHY (UV DETECTION), & 8-13 NG IN THIN-LAYER CHROMATOGRAPHY (UV DETECTION). CHLORAZINE WAS ANALYZED.|Ten systems are described for identification of 61 pesticides, most of which are herbicides, by thin-layer chromatography. One of the herbicides mentioned is chlorazine.|A PROCEDURE IS DISCUSSED FOR ANALYSIS OF CHLORAZINE IN WASTE WATER USING GAS-LIQ CHROMATOGAPHY.

Procedure for determining s-triazine herbicides in urine & biological tissues by gas chromatography/flame ionization detection is described. Urine samples are extracted with ether & biological tissues with chloroform. Residues obtained after evaporation of solvent are dissolved in dimethylformamide. Most of the lipids can be removed by n-pentane partitioning. /s-Triazine herbicides/|Analytical methodology for the separation and characterization of s-triazine residues in urine was developed. In the sample preparation procedure developed, a urine sample at pH 12 was extracted with hexane 3 times, using sodium chloride as an emulsion inhibitor. The combined hexane extract was dried by passing it through a sodium sulfate column and concentrated by rotary evaporation. The sample was transferred to a centrifuge tube and further concentrated to 0.5 ml under a stream of dry nitrogen. The sample was analyzed by gas chromatography using the Hall electrolytic conductivity detector in the nitrogen-specific mode. /s-Triazines/

Computed Properties

Molecular Weight:257.76
XLogP3:3.8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:257.1407234
Monoisotopic Mass:257.1407234
Topological Polar Surface Area:45.2
Heavy Atom Count:17
Complexity:188
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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