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Chlormequat Chloride

HCID 13836
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Basic information

CAS
999-81-5
Standard SMILES
C[N+](C)(C)CCCl.[Cl-]
InChIKey
UHZZMRAGKVHANO-UHFFFAOYSA-M
Molecular formula
C5H13ClN.Cl
Average molar mass
158.07 g/mol
Monoisotopic mass
157.0425048

Overview

Chlormequat chloride appears as white crystals with a fishlike odor. Used as a plant growth regulator. Said to be effective for cereal grains, tomatoes, and peppers. (EPA, 1998)

Names & identifiers

Preferred name
Chlormequat Chloride
IUPAC
2-chloroethyl(trimethyl)azanium chloride
English name
Chlormequat chloride
Molecular formula
C5H13Cl2N
Molecular weight
158.07

Names & synonyms

Chlormequat chloride999-81-5Chlorocholine chloride2-Chloro-N,N,N-trimethylethanaminium chloride(2-Chloroethyl)trimethylammonium chlorideAntywylegaczCycoganCyclocelStabilanCyocelRetacelCycogan extra
Show more names
CHLORMEQUATTURCYCOCEL(2-CHLORETHYL)TRIMETHYLAMMONIUM CHLORIDEExtraCCC700CECECE
Choline dichlorideBarleyquatBettaquatFarmacelHalloweenHelstoneIncrecelHyquat

Database identifiers

CAS
999-81-5
PubChem CID
13836
DTXSID
DTXSID6020303
ChEMBL
CHEMBL118539
ChEBI
CHEBI:137392
UNII
PPL2215L82
EC Number
213-666-4

Properties

Computed structural properties

Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
8
Formal charge
0
Complexity
46.5

Experimental & physicochemical properties

pHpH = 5.14
PesticidesPesticides -> Plant Growth Regulators
LogPlog Kow = -3.80
Odor · 2 items

TYPICAL AMINE ODOR

Fish-like odor

Density1.14 to 1.15 g/mL at 20 °C
Color/Form · 2 items

White cyrstalline solid

Colorless crystals

Solubility · 6 items

greater than or equal to 100 mg/mL at 73 °F (NTP, 1992)

SOL IN LOWER ALC SUCH AS METHANOL; INSOL IN ETHER & HYDROCARBONS; WATER SOLUBILITY 74% @ 20 °C

In ethanol, 320 g/kg at 20 °C.

Solubility in methanol: >25 kg/kg at 20 °C, dichloroethane, ethyl acetate, n-heptane, and acetone <1, chloroform 0.3 (all in g/kg, 20 °C).

In water, 9.96X10+5 mg/L at 20-25 °C

Solubility in water, g/100ml at 20 °C: 74 (good)

CorrosivityAqueous solutions are corrosive to metal
Decomposition245 °C
Melting Point · 2 items

473 °F Decomposes (EPA, 1998)

239 °C (decomposes)

Vapor Pressure · 5 items

7.5e-08 mmHg at 68 °F (NTP, 1992)

0.00000008 [mmHg]

7.5X10-8 mm Hg at 20 °C

Vapor pressure at 20 °C: negligible

0.000000075 [mm Hg] @20 °C

Surface Tension70.3 mN/m

Physicochemical properties

Melting point
239 · 239-243 °C (dec.)(lit.)
Boiling point
260.3 °C · 260.3°C (rough estimate)
Density
1.2228 · 1.2228 (rough estimate)
refractive index
1.55 · 1.5500 (estimate)
storage temp.
Inert atmosphere,Room Temperature
solubility
DMSO (Slightly), Methanol (Slightly)
form
Crystalline Powder or Crystals
color
White to off-white
Odor
Foul odor
Water Solubility
almost transparency
Sensitive
Hygroscopic
Merck
14 · 14,2104
BRN
3563994 · 3563994
Henry's Law Constant
3.2 · 3.2×109 mol/(m3Pa) at 25℃, Maniere et al. (2011)
Stability
Stable. Combustible. Incompatible with strong oxidizing agents. Corrodes many metals. Very hygroscopic.
Major Application
agricultureenvironmental
InChI
1S/C5H13ClN.ClH/c1-7(2,3)5-4-6;/h4-5H2,1-3H3;1H/q+1;/p-1
InChIKey
UHZZMRAGKVHANO-UHFFFAOYSA-M
SMILES
[Cl-].C[N+](C)(C)CCCl
Toxicology and Carcinogenesis
Bioassay of (2-Chloroethyl)trimethylammonium Chloride (CCC) for Possible Carcinogenicity (CASRN 999-81-5)
CAS DataBase Reference
999 · 999-81-5(CAS DataBase Reference)
EWG's Food Scores
1 · 1
NCI Dictionary of Cancer Terms
TUR
FDA UNII
2215 L82 · PPL2215L82
Pesticides Freedom of Information Act (FOIA)
Chlormequat chloride
EPA Substance Registry System
Chlormequat chloride (999-81-5)
UNSPSC Code
41116107 · 41116107
NACRES
72 · NA.72
Symbol(GHS)
6 · GHS06
Signal word
Danger
Hazard statements
302 · H302-H311
Precautionary statements
264 · P264-P270-P280-P301+P312-P302+P352+P312-P361+P364
PPE
95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
Hazard Codes
Xn
Risk Statements
21 · 21/22
Safety Statements
36 · 36/37
RIDADR
2811 · UN 2811 6.1/PG 3
WGK Germany
2 · 2
RTECS
5250000 · BP5250000
F
3 · 3-10
TSCA
TSCA listed
HazardClass
6.1 · 6.1
PackingGroup
III
HS Code
29239000 · 29239000
Storage Class
6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 4 Oral
Hazardous Substances Data
999 · 999-81-5(Hazardous Substances Data)
Toxicity
50 in · LD50 in mice (mg/kg): 7 i.v., 54 orally (Hennighausen, Wiegershausen)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P280, P301+P317, P302+P352, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Warning

H302 (85.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Regulation (EC) No 396/2005 (amended)

Chlormequat chloride is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

Chlormequat chloride: Does not have an individual approval but may be used under an appropriate group standard

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.)

Other Safety InformationIMAP assessments - Ethanaminium, 2-chloro-N,N,N-trimethyl-, chloride: Environment tier I assessment
DOT LabelPoison
Fire Hazards · 2 items

Flash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)

Not combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Fire PotentialNoncombustible solid.
Health HazardsInhalation of spray and prolonged or repeated contact with skin should be avoided. (EPA, 1998)
Hazards Summary · 1 item

A mild eye irritant; Can be absorbed through skin; The substance may cause effects on the nervous system: cholinergic symptoms without acetylcholinesterase inhibition. [ICSC] An irritant; Can be absorbed through skin; Effects in high-dose animal studies include convulsions; [MSDSonline] Toxic to hamster embryos; No human data; [REPROTOX]

Reactive GroupHalogenated Organic Compounds
EC ClassificationSymbol: Xn; R: 21/22; S: (2)-36/37
Special Reports · 2 items

USEPA/Office of Pesticides Programs; Reregistration Eligibility Decision for Chlormequat Chloride (EPA 738-R-07-014) 73 pp. (September 25, 2007)

DHEW/NCI; Bioassay of (2-Chloroethyl)trimethylammonium chloride for Possible Carcinogenicity (1979) Technical Rpt Series No. 158 DHEW Pub No. (NIH) 79-1714

FIFRA Requirements · 2 items

The Agency has completed its review of submitted data and its assessment of the dietary (drinking water only), occupational and ecological risks associated with the use of pesticide products containing the active ingredient chlormequat chloride. Dietary (food) risks were not assessed because there are no food/feed uses of chlormequat chloride. Based on a review of the chlormequat chloride data, the Agency has sufficient information on the human health and ecological effects of chlormequat chloride to make decisions as part of the reregistration process under FIFRA. The Agency has determined that currently registered uses of chlormequat chloride will not pose unreasonable risks or adverse effects to humans or the environment provided that the risk mitigation measures and label changes outlined in this RED are implemented; therefore, products containing chlormequat chloride are eligible for reregistration.

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. Chloroethyl trimethyl ammonium chloride is found on List C. Case No: 3003; Pesticide type: Fungicide, Herbicide, Antimicrobial; 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 Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Chloroethyl trimethyl ammonium chloride; Data Call-in (DCI) Date(s): 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.

Reactivity ProfileCHLORMEQUAT CHLORIDE is incompatible with strong oxidizing agents. It is corrosive to unprotected metals. (NTP, 1992)

Safety & protection

Fire Fighting · 2 items

(Non-Specific -- Poisonous Solid, n.o.s.) For small fires, use dry chemical, carbon dioxide, water spray, or foam. For large fires, use water spray, fog, or foam. (EPA, 1998)

In case of fire in the surroundings, use appropriate extinguishing media.

First Aid Measures · 4 items

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

First Aid · 1 item

Signs and Symptoms of Chlormequat Chloride Exposure: No information on specific clinical effects of exposure to chlormequat chloride was found in available references. However, because chlormequat chloride is expected to be corrosive, irritation and burning of the skin, eyes, and mucous membranes may be noted. Light-headedness, drowsiness, slurred speech, pupillary dilation, increased salivation, dysphagia (difficulty swallowing), abdominal pain, and spontaneous vomiting may occur. Stridor (high pitched, noisy respirations), dyspnea (shortness of breath), and pulmonary edema may occur. Apathy and mental confusion may develop, with progression to coma and death.

Safe StorageDry. Keep in a well-ventilated room. Store in glass, high-density plastic, rubber or epoxy resin-protected metal containers.
Storage Conditions · 2 items

Pesticide Storage: Store in original container. DO NOT store below freezing temperatures.

It may be stored in containers of glass or high density plastics, or of metal lined with rubber or epoxyresin.

Cleanup MethodsSweep spilled substance into containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment. (Extra personal protection: P2 filter respirator for harmful particles).
Nonfire Spill Response · 1 item

(Non-Specific -- Poisonous Solid, n.o.s.) Keep unnecessary people away. Isolate hazard area and deny entry. Stop leak if you can do it without risk. For small spills: take up with sand or other noncombustible absorbent material and place into containers for later disposal.

Disposal Methods · 3 items

Pesticide Disposal: Wastes resulting from the /agricultural/ use of this product may be disposed of on site or at an approved waste disposal facility. Container Disposal: Triple rinse (or equivalent). Then offer for recycling or reconditioning or puncture and dispose of in /accordance with local, state, and Federal laws/.

This crystalline, water-soluble solid melts at 245 °C with decomp. Incineration is a highly effective disposal method. Heating the product with strong aqueous alkali would result in decomp with the evolution of trimethylamine and other gaseous products. Recommendable method: Incineration. Peer-review: Incinerate in a unit with effluent gas scrubbing. (Peer-review conclusions of an IRPTC expert consultation (May 1985))

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.

Spillage Disposal · 1 item

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations.

Preventive Measures · 5 items

End Use Products Intended for Occupational Use. 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 materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them.

End Use Products Intended for Occupational Use. Users should wash hands before eating, drinking, chewing gum, using tobacco, or using the toilet.

End Use Products Intended for Occupational Use. Users should remove clothing/PPE immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing.

End Use Products Intended for Occupational Use. Users should 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.

For more Preventive Measures (Complete) data for CHLORMEQUAT CHLORIDE (10 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Eye PreventionWear face shield or eye protection in combination with breathing protection.

Toxicology

Ecotoxicity Values · 5 items

LD50 Anas platyrhynchos (Mallard) male oral 265 mg/kg (95% confidence limit 211-334 mg/kg) 3 mo old /sample purity 98%/

LD50 Quail oral 555 mg/kg

LD50 Pheasant oral 261 mg/kg

LC50 Phasianus colchicus (ring-necked pheasant, age 10-15 days) diet >5000 ppm for 8 days

For more Ecotoxicity Values (Complete) data for CHLORMEQUAT CHLORIDE (18 total), please visit the HSDB record page.

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 203(2), indicates that chlormequat chloride is expected to have moderate mobility in soil(SRC). However, this compound exists as a quaternary ammonium cation and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3). In soils, the primary fate processes for the chlormequat chloride cation are expected to be biodegradation and adsorption(SRC). Volatilization from moist soil is not expected because the base exists as a cation and cations do not volatilize. Chlormequat chloride is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). In soil, chlormequat chloride is degraded rapidly by microbial activity(2). Half-lives in 4 soils were reported as averaging 32 days at 10 °C and 1 to 28 days at 22 °C(2).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 203(2) indicates that chlormequat chloride is not expected to adsorb to suspended solids and sediment(SRC). However, this compound exists as a quaternary ammonium cation and therefore would be expected to adsorb strongly to sediments and suspended matter, clay minerals, and other materials with negative surface charges(7). In water, the primary fate processes for the chlormequat chloride cation are expected to be biodegradation and adsorption(SRC). Chlormequat chloride is a quarternary cation at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3.2(SRC), from its log Kow of -3.80(4) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Although no biodegradation data were located for the chlormequat chloride cation in water, chlormequat chloride has been reported to be degraded rapidly by microbial activity in soil(2), suggesting that biodegradation in water could occur. Adsorption to sediments does not appear to reduce biodegradability of some quaternary ammonium compounds; although adsorption to certain clay minerals may retard biodegradation(3). Based on analogy to other quaternary ammonium compounds(3), the reduction of biomass or other nutrient materials in natural water may reduce the biodegradation rate of the chlormequat chloride cation and acclimation enhances biodegradation of quaternary ammonium compounds.

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlormequat chloride, which has a vapor pressure of 7.50X10-8 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlormequat chloride 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 2.2 days(SRC), calculated from its rate constant of 7.4X10-12 cu cm/molecule-sec at 25 °C that was derived using a structure estimation method(3). Particulate-phase chlormequat chloride may be removed from the air by wet or dry deposition(SRC). Chlormequat chloride does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure RoutesThe substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
Milk ConcentrationsChlormequat was determined in four /sow/ milk samples in the range of 0.4 ng/g to 1.2 ng/g...
Ecotoxicity Excerpts · 5 items

/BIRDS and MAMMALS/ /An/ ...avian reproduction study with the Japanese quail... had mean-measured concentrations of 158, 387 and 982 mg/kg diet. The study was conducted with a two week pre-treatment period followed by a 6-week exposure period, rather than the guideline 10-week pre-laying exposure followed by a 10-week egg-laying exposure period. The most sensitive endpoints were the adult parameters of food consumption and male body weight gain; both endpoints showed significant adverse effects at all treatment levels. As a result, the required NOAEC could not be statistically determined (<158 mg ai/kg diet) from this study. The most sensitive reproductive parameter was a significant reduction in hatchlings per eggs set and number of cracked eggs in the highest test concentration. Additionally, absolute testes weight was significantly reduced (by 16%) in the 982 mg/kg group and there was a significant increase in egg shell thinning and decreased egg strength at the highest test concentration. These reductions may reflect effects on endocrine-mediated processes.

/AQUATIC SPECIES/ In a 21-day chronic toxicity study on the water flea, ...a NOAEC of 5.0 mg ai/L was reported based on a statistically significant 20% reduction in live offspring relative to the control.

/AQUATIC SPECIES/ One supplemental subacute 21-day toxicity study following OECD 204 was reviewed. ...Rainbow trout were exposed to chlormequat chloride concentrations of 43, 100, 250, 590, 1400 and 3400 mg/L. By the sixth day of the study (guideline acute fish toxicity tests are 96 hr), 90% of the fish in the 3400 mg ai/L concentration were dead. No other treatment-related mortalities were observed. Therefore, the NOAEC for this study is 1400 mg ai/L and the LC50 is >1400 mg ai/L, which results in chlormequat chloride being classified as practically non-toxic to freshwater fish on an acute exposure basis.

/AQUATIC SPECIES/ Chlormequat is classified as moderately toxic to the aquatic vascular plant Lemna gibba based on reductions in all measured parameters, the most sensitive being frond number, with an EC50 of 2.8 mg ai/L and a NOEC of 0.04 mg ai/L. Chlormequat chloride is less toxic to nonvascular plants such as green algae Scenedesmus subcapitatus with a 96-hr EC50 >899 mg ai/L and a NOAEC of 233 mg ai/L and blue-green algae (cyanobacteria; Anabaena flosaquae) with an EC50 >207 mg ai/L and a NOAEC=207 mg ai/L.

/MAMMALS and BIRDS/ /In 3 month old male mallards/ LD50 at 95% confidence level was 265 mg/kg chlormequat chlorine. Signs of intoxication: Ataxia, miosis, falling, sitting, using wings for pedestrian locomotion, tremors, tetanic seizures, immobility, opisthotonos, and frequent spasms. Signs appeared as soon as 5 min and mortalities usually occurred between 15 and 40 min after /oral/ treatment. Remission took up to 3 days.

Signs and Symptoms · 4 items

See Ingestion.

MAY BE ABSORBED!

Redness.

Excessive salivation. Sweating. Diarrhoea. Dizziness. Headache. Laboured breathing. Nausea. Pupillary constriction.

Acute Toxicity LinkChemical: CHLORMEQUAT CHLORIDE
Ongoing Test Status · 1 item

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=999-81-5]

ICSC Environmental DataThe substance is harmful to aquatic organisms. Avoid release to the environment in circumstances different to normal use.
Soil Adsorption/Mobility · 1 item

The Koc of chlormequat chloride has been reported to be 203(1). According to a classification scheme(2), this Koc value suggests that chlormequat chloride is expected to have moderate mobility in soil. However, this compound exists as a quaternary ammonium cation and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(3). Chlormequat chloride is expected to adsorb strongly to various materials, including suspended solids in wastewater treatment facilities, sediments in rivers and lakes, suspended organics and minerals in natural water systems, clays, proteins, and microorganisms(4-6). Further, adsorption of quaternary ammonium compounds to river sediment occurs primarily by an ion-exchange mechanism(5). Monitoring studies of river water samples from Germany reported that 50% of an alkyltrimethyl quaternary ammonium compound detectable in the water column was associated with suspended solids in the water; the suspended solids in the water comprise a small fraction of the water(7).

Human Toxicity Excerpts · 4 items

/CASE REPORTS/ The suicide of a young man with the plant growth regulator Cycocel (chlorocholine chloride and choline chloride) is reported. Morphological and toxicological findings are presented...

/CASE REPORTS/ Discussion of a case of acute contact dermatitis caused by occupational exposure to the growth inhibitor cycocel.

/CASE REPORTS/ A case was provided of accidental ingestion of Cycocel which manifested as a cholinergic crisis that led to sudden death. The patient was a 59 yr old male nursery worker who accidentally drank a mouthful of plant growth chemical Cycocel, containing the active ingredient (2-chloroethyl)trimethylammonium chloride (chlormequat). Initially he was seen by his family physician and indicated he had not swallowed any of the liquid. He later realized that he must have swallowed some of the liquid. An electrocardiogram revealed-T wave inversion and flat AVF. Following transfer to the hospital, the patient suffered a seizure, demonstrated bradycardia, experienced severe dysrhythmia followed by ventricular fibrillation which eventually resulted in asystole. Autopsy results indicated marked pulmonary edema, coronary atherosclerosis, atheromata of aorta, and localized adenocarcinoma of the prostate. Chlormequat was detected in the stomach contents and urine. The Cycocel the patient ingested apparently was kept in a refrigerator at the nursery along with bottled drinking water. The appearance of these solutions is similar; however, the cycocel has a fishy smell.

/ENDOCRINE MODULATION/ Twenty-four pesticides /including chlormequat chloride/ were tested for interactions with the estrogen receptor (ER) and the androgen receptor (AR) in transactivation assays. Estrogen-like effects on MCF-7 cell proliferation and effects on CYP19 aromatase activity in human placental microsomes were also investigated. .../Chlormequat chloride was inactive in all assays reported./

Regulatory information

FIFRA Requirements · 2 items

The Agency has completed its review of submitted data and its assessment of the dietary (drinking water only), occupational and ecological risks associated with the use of pesticide products containing the active ingredient chlormequat chloride. Dietary (food) risks were not assessed because there are no food/feed uses of chlormequat chloride. Based on a review of the chlormequat chloride data, the Agency has sufficient information on the human health and ecological effects of chlormequat chloride to make decisions as part of the reregistration process under FIFRA. The Agency has determined that currently registered uses of chlormequat chloride will not pose unreasonable risks or adverse effects to humans or the environment provided that the risk mitigation measures and label changes outlined in this RED are implemented; therefore, products containing chlormequat chloride are eligible for reregistration.

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. Chloroethyl trimethyl ammonium chloride is found on List C. Case No: 3003; Pesticide type: Fungicide, Herbicide, Antimicrobial; 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 Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): Chloroethyl trimethyl ammonium chloride; Data Call-in (DCI) Date(s): 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.

CERCLA Reportable Quantities · 1 item

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. Chlormequat chloride 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 ... .

Safety data

F
3-10
PPE
dust mask type N95 (US), Eyeshields, Faceshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
BP5250000
ridadr
UN 2811 6.1/PG 3
hs_code
29239000
Toxicity
LD50 in mice (mg/kg): 7 i.v., 54 orally (Hennighausen, Wiegershausen)
risk_code
21/22
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
Xn
safety_code
36/37
hazard_class
6.1
Storage Class
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group
III
Hazard statements
H302-H311
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 4 Oral
Precautionary statements
P264-P270-P280-P301+P312-P302+P352+P312-P361+P364
Hazardous Substances Data
999-81-5(Hazardous Substances Data)

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

Chlormequat chloride has been reported in the literature to act at the nicotinic receptor site of the neuromuscular junction. The test material may act as a depolarizing agent at this site, leading to muscular excitation followed by muscle weakness. Acute toxicity may lead to respiratory arrest. Acute toxicity of chlormequat chloride has also been reported to differ by species, which is likely due to sensitivity to depolarizing neuromuscular blockers.

Metabolism/Metabolites · 5 items

An experiment was conducted to evaluate the metabolic products of chlorocholine chloride (CCC) in eggs and meat of laying hens fed a diet containing (15)N-CCC. Ten brown laying hens were randomly divided into two groups of five each. One group was offered (15)N-CCC free diet while the other group received a diet with 100 ppm (15)N-CCC for 11 days. Samples of eggs and meat from the laying hens were collected. Egg yolks and albumen were separated. Meat was collected from the breast and femur. The metabolic products of CCC were measured using ion trap electrospray ionization mass spectrometry (ion trap-ESI-MS/MS). Determination of CCC or its metabolites in eggs and meat showed that CCC was metabolized to choline. Corresponding MS/MS spectra were obtained for m/z 104 (choline) or 105 ((15)N-choline), whereas nothing was detected at m/z 122 (CCC) or 123 ((15)N-CCC). The results from this study indicate that CCC will be metabolized in tissues of laying hens.

When (14)C-labeled CCC was applied to kohlrabi, cauliflower, or tomatoes, degradation of CCC was very small. The first product was probably choline which entered the plant pool. Small amounts of labeled methyl groups from choline were found as S-methyl methionine. CCC was not degraded when applied to sugarcane. In alfalfa, CCC was slowly metabolized and was primarily incorporated into choline of phosphatidylcholine.

Almond seedlings were treated with labeled CCC. Translocation to leaves and to the roots was observed. (14)CO2 was formed within 2 h after application. Radioactivity was observed in 17 known amino acids, an unidentified ninhydrin positive compound, malic acid, citric acid, choline and 2-chloroethylamine.

When CCC was incubated in rumen contents or juice under anaerobic conditions, microbial degradation of CCC did not occur.

For more Metabolism/Metabolites (Complete) data for CHLORMEQUAT CHLORIDE (7 total), please visit the HSDB record page.

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.
Absorption, Distribution and Excretion · 3 items

Chlormequat was determined in four /sow/ milk samples in the range of 0.4 ng/g to 1.2 ng/g...

The distribution of Chlorocholine chloride (CCC) in the eggs of laying hens was studied using 15N-CCC. Twelve layers (37 weeks old) were divided into four groups and used in this study consisting of three feeding phases. In phase one (7 days), all the hens received a CCC-free diet [165 g CP/kg dry matter (DM); 11.58 MJ ME/kg DM]. In phase two (11 days), four levels of 15N-CCC: 0, 5, 50 and 250 ppm were added to the respective diets, while in phase three (7 days), CCC-free feed was again offered. Egg samples were taken and the 15N content of egg yolk and albumin were determined. At the end of phase two, there was a significant (p < 0.05) increase in 15N content in egg yolk from hens fed the 50 and 250 ppm CCC diets and in albumin from hens fed the 250 ppm CCC diet. The estimated 15N-CCC residue was 1.71, 6.64, 28.80 ppm in egg yolk and 1.58, 1.08 and 4.50 ppm in albumin from hens fed 5, 50 and 250 ppm CCC, respectively. The CCC residue, from quantitative analysis ranged from 0.21 to 0.93 and 0.93 to 2.43 ppm in yolk of hens fed 50 and 250 ppm CCC, respectively, whereas a range of 0.40-1.46 ppm, was found in the albumin of hens fed 250 ppm. The difference in measured CCC in yolk and albumin and that estimated from 15N-CCC could have been due to breakdown products of 15N-CCC. Seven days after withdrawal of 15N-CCC, the estimated 15N-CCC residue in egg yolk decreased to 0.43, 2.45 and 15.59 ppm, on 5, 50 and 250 ppm CCC dietary treatments, respectively, and to 2.46 ppm in albumin from hens fed 250 ppm CCC. The higher increase in 15N content could have been due to a higher incorporation of 15N-CCC into yolk than albumin during the process of rapid yolk deposition. This experiment showed that consumed CCC is distributed both into yolk and albumin in a dose dependent manner and that CCC is metabolized in laying hens. However, the level of CCC in the diet which could lead to accumulation of detectable CCC levels in eggs as observed in this study, is much higher than the established maximum residual limits in grains.

In mammals, following oral administration, 97% is eliminated within 24 hr, principally as the unchanged substance.

Uses & manufacturing

Uses · 6 items

Used as plant growth regulator; [Merck Index] Works by inhibiting the biosynthesis of a plant hormone; Registered for use on ornamental plants grown in greenhouses and nurseries; May be used outside in containerized ornamentals; [Reference #1]

Farming (Pesticides) [Category: Industry]

For chlormequat chloride (USEPA/OPP Pesticide Code: 018101) 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./

Used to increase resistance to lodging ... and to increase yields in wheat, rye, oats, and triticale; to promote lateral branching and flowering in azaleas, fuchsias, begonias, poinsettias, geraniums, pelargoniums, and other ornamental plants; to promote flower formation and improve fruit setting in pears, almonds, vines, olives, and tomatoes; to prevent premature fruit drop in pears, apricots, and plums. Also used on cotton, vegetables, tobacco, sugar cane, mangoes, and other crops.

Plant growth regulator for cotton, grapes, vegetables, mango, tobacco, ornamentals, and greenhouse use on azaleas, poinsettias, geraniums, and hibiscus.

Chlormequat chloride is currently registered for use on a wide variety of ornamentals grown in greenhouses, shadehouses, and nurseries. Crops include herbaceous and woody annual and perennial plants such as begonias, vincas, azaleas, and poinsettias. Outdoor use is restricted to containerized ornamentals. Chlormequat chloride has no residential or food uses; therefore, there are no associated tolerances.

U.S. Production · 2 items

(1976) PROBABLY GREATER THAN 2.27X10+6 G

(1978) PROBABLY GREATER THAN 2.27X10+6 G

Methods of Manufacturing · 3 items

Condensation of triethylamine and ethylene dichloride

Prepd from choline chloride & benzenesulfonyl chloride; from choline chloride & thionyl chloride.

It is synthesized from trimethylamine and 1,2-dichloroethane.

Formulations/Preparations · 5 items

CHLORMEQUAT CHLORIDE TECHNICAL: Active Ingredient 66.0% Chlormequat chloride

CHLORMEQUAT E-PRO PLANT GROWTH REGULATOR: Active Ingredient 11.8% Chlormequat chloride

CITADEL: Active Ingredient 11.8% Chlormequat chloride

CYCOCEL PLANT GROWTH REGULANT: Active Ingredient 11.8% Chlormequat chloride

For more Formulations/Preparations (Complete) data for CHLORMEQUAT CHLORIDE (12 total), please visit the HSDB record page.

Use ClassificationGROWTH REGULATORS
General Manufacturing Information · 6 items

Ethanaminium, 2-chloro-N,N,N-trimethyl-, chloride (1:1): ACTIVE

Cycocel is a plant growth regulant preventing lodging of cereals in cereal crops ... treated plants are generally compact & sturdy & have typically shortened internodes, dark green leaves & shortened petioles. Plants usually remain dwarfed under optimal watering & fertilization.

Chlormequat chloride applications are applied using several types of application equipment -- including ... low-pressure handwands, backpack sprayers, and high-pressure handwands.

Mixtures with other growth regulator herbicides and with urea are possible, but should be applied immediately after mixing.

... Effective in ... crops such as vegetables (tomatoes, capsicum, cabbage, cauliflower, radishes, cucurbits, peas), grape vines, mango, tobacco, etc. /Former/

... Plant growth regulator which influences the habit of certain plants by shortening and strengthening the stem ... . It can also influence the developmental cycle resulting in increased flowering and harvest.

Applications · 4 items

DescriptionChlormequat chloride is a white to yellowishcrystalline solid with a fish-like odor. Molecularweight=158.1; Freezing/Melting point=245℃ (decomposes); Hazard Identification (based on NFPA 704 M RatingSystem): Health 3, Flammability 0, Reactivity 0. Highly soluble in water. Carrier solvents used in commercial productsmay alter physical and toxicological properties.

UsesChlorocholine Chloride is a plant growth regulator that is primarily used on ornamental plants.

UsesPlant growth regulator on ornamental plants.

General DescriptionWhite crystals with a fishlike odor. Used as a plant growth regulator. Said to be effective for cereal grains, tomatoes, and peppers.

Upstream & downstream products

Upstream raw materials

TrimethylamineDichloroethaneBromocholine chlorideCHOLINE

Additional notes

DefinitionA phytocidal bipyridilium quaternary ammonium salt.

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