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Carbanolate

Carbanolate structure

Carbanolate 

structure
  • CAS No:

    671-04-5

  • Formula:

    C10H12ClNO2

  • Chemical Name:

    Carbanolate

  • Synonyms:

    Phenol,2-chloro-4,5-dimethyl-,1-(N-methylcarbamate);Carbamic acid,methyl-,6-chloro-3,4-xylyl ester;Phenol,2-chloro-4,5-dimethyl-,methylcarbamate;Banol;6-Chloro-3,4-dimethylphenyl N-methylcarbamate;6-Chloro-3,4-xylyl methylcarbamate;Carbanolate;3,4-Xylyl-6-chloro-N-methylcarbamate;3,4-Dimethyl-6-chlorophenyl N-methylcarbamate;2-Chloro-4,5-dimethylphenyl N-methylcarbamate;2-Chloro-4,5-dimethylphenyl methylcarbamate

Description

Carbanolate is a carbamate ester that is phenyl methylcarbamate which is substituted by a chloro group at position 2 and by methyl groups at positions 4 and 5, respectively. It is an insecticide used in the the control of poultry ectoparasites. It has a role as a carbamate insecticide, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an acaricide. It is a member of monochlorobenzenes and a carbamate ester.

Carbanolate Basic Attributes

213.66

213.66

M05Z0Q9XTF

DTXSID7041754

CRYSTALLINE SOLID

2924299090

Characteristics

38.3

2.56

1.2±0.1 g/cm3

130-133 °C

306.8±42.0 °C at 760 mmHg

139.3±27.9 °C

1.530

SOLUBILITY: ACETONE 25%, BENZENE 14%, TOLUENE 10%, XYLENE 6.7%, KEROSENE LESS THAN 2%

Oral-Rat  LD50: 30 mg/kg; Oral-Mouse LD50: 300 mg/kg

Combustion produces toxic nitrogen oxides and chloride gases

NON-CORROSIVE

Safety Information

II

6.1(a)

2757

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

DECOMP IN ALKALI

P264, P270, P301+P310, P321, P330, P405, P501

H300

|Danger|H300: Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501

Toxicity

most toxic

Drug Information

FOLLOWING SUBACUTE ORAL ADMIN OF BANOL TO RATS, ELIMINATION WAS...COMPLETE WITHIN 48 HR. METHYLAMINE TO CARBON DIOXIDE WERE IDENTIFIED AS METABOLITES. A NUMBER OF OTHER METABOLITES INCL GLUCURONATES WERE OBSERVED BUT NOT IDENTIFIED. IN MORE RECENT STUDIES, 2-CHLORO-4,5-XYLYL N-HYDROXYMETHYLCARBAMATE AND 2-CHLORO-4,5-XYLENOL WERE IDENTIFIED AFTER INCUBATION OF BANOL IN RAT LIVER MICROSOME-NADPH2 SYSTEM. ... DEGRADATION OF BANOL BY MICROSOMES OR BY WHOLE BLABERUS GIGANTEUS FAT BODY RESULTED IN FORMATION OF AT LEAST 3 METABOLITES. ONE OF THESE WAS N-HYDROXYMETHYL BANOL.|NATURE OF METABOLITES OF BANOL STUDIES USING (14)C-LABEL AT CARBONYL, 4-METHYL, & N-METHYL GROUPINGS. THE LIVER PREPN WERE ABOUT EQUAL IN THEIR RATES OF BIOTRANSFORMATION... CARBOXYLIC ACIDS...TOGETHER WITH SMALL AMT OF CORRESPONDING PHENOLIC ACIDS (3-4%), FORMED BY SUBSEQUENT ESTERATIC CLEAVAGE, WERE THE MAJOR ETHER-SOL PRODUCTS (8-14%). ONLY RAT LIVER YIELDED THE N-HYDROXYMETHYLCARBAMATE (6%).|BANOL YIELDS 2-CHLORO-4,5-DIMETHYLPHENOL & 2-CHLORO-4,5-DIMETHYLPHENYL HYDROXYMETHYLCARBAMATE IN MAN & IN RAT. STROTHER A; TOXICOL APPL PHARMAC 21: 112 (1972). OONNITHAN ES & CASIDA JE; J AGRIC FD CHEM 16: 28 (1968). 2-CHLORO-4,5-DIMETHYLPHENYL HYDROXYMETHYLCARBAMATE ALSO IN BEANS. KUHR RJ & CASIDA JE; J AGRIC FD CHEM 15: 814 (1967). /FROM TABLE/|THERE IS NO EVIDENCE TO SUGGEST THAT MONOALKYLCARBAMATES SUCH AS...CARBANOLATE ARE DEALKYLATED DIRECTLY; RATHER, THEY ARE ATTACKED BY N-METHYLHYDROXYLATION & SUBSEQUENTLY CONJUGATED.|For more Metabolism/Metabolites (Complete) data for CARBANOLATE (6 total), please visit the HSDB record page.

1) ESTABLISH CLEAR AIRWAY & TISSUE OXYGENATION BY ASPIRATION OF SECRETIONS & IF NECESSARY, BY ASSISTED PULMONARY VENTILATION WITH OXYGEN. IMPROVE TISSUE OXYGENATION AS MUCH AS POSSIBLE BEFORE ADMINISTERING ATROPINE TO MINIMIZE THE RISK OF VENTRICULAR FIBRILLATION. /CARBAMATES, CHOLINESTERASE INHIBITORS/|2) ADMIN ATROPINE SULFATE IV, OR IM IF IV INJECTION IS NOT POSSIBLE... IN MODERATELY SEVERE POISONING: ADULT DOSAGE, INCLUDING CHILDREN OVER 12 YR: 0.4-2.0 MG REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED (TACHYCARDIA, FLUSHING, DRY MOUTH, MYDRIASIS). MAINTAIN ATROPINIZATION BY REPEATED DOSES FOR 2-12 HR, OR LONGER, DEPENDING ON SEVERITY OF POISONING... DOSAGE FOR CHILDREN UNDER 12 YEARS: 0.05 MG/KG BODY WT REPEATED EVERY 15 MIN UNTIL ATROPINIZATION IS ACHIEVED. MAINTAIN ATROPINIZATION WITH REPEATED DOSAGE OF 0.02-0.05 MG/KG. SEVERELY POISONED INDIVIDUALS MAY EXHIBIT REMARKABLE TOLERANCE TO ATROPINE; TWICE THE DOSES SUGGESTED ABOVE MAY BE NEEDED... /CARBAMATES, CHOLINESTERASE INHIBITORS/|3. PRALIDOXIME (PROTOPAM-AYERST, 2-PAM) IS OF DOUBTFUL VALUE IN POISONINGS BY CARBAMATE INHIBITORS OF CHOLINESTERASE. ATROPINE ALONE IS ALMOST ALWAYS AN ADEQUATE ANTIDOTE. PRALIDOXIME IS PROBABLY CONTRAINDICATED IN POISONINGS BY CARBARYL, SPECIFICALLY. IF VICTIM OF CARBAMATE POISONING EXHIBITS SEVERE MUSCLE WEAKNESS &/OR RESPIRATORY DEPRESSION, OR IF POISONING INVOLVES A COMBINATION OF CARBAMATE & ORGANOPHOSPHATE, A DILUTE SOLUTION OF PRALIDOXIME (TOTAL DOSE IN 250 ML 5% GLUCOSE SOLN) MAY BE GIVEN CAUTIOUSLY IV. THE INFUSION SHOULD BE TERMINATED IF PATIENT'S CONDITION WORSENS. PRALIDOXIME DOSAGE: ADULTS, 1.0 G; FOR CHILDREN UNDER 12 YR, 20-50 MG/KG. 4. OBSERVE TREATED PATIENTS CLOSELY AT LEAST 24 HR TO INSURE THAT SYMPTOMS (POSSIBLY PULMONARY EDEMA) DO NOT RECUR AS ATROPINIZATION WEARS OFF. IN VERY SEVERE POISONINGS, METABOLIC DISPOSITION OF TOXICANT MAY REQUIRE SEVERAL HR OR DAYS DURING WHICH ATROPINIZATION MUST BE MAINTAINED. /CARBAMATES, CHOLINESTERASE INHIBITORS/|5. BATHE & SHAMPOO VICTIM WITH SOAP & WATER IF THERE IS ANY CHANCE THAT SKIN & HAIR ARE CONTAMINATED. 6. IF PESTICIDE HAS BEEN INGESTED IN QUANTITY SUFFICIENT TO CAUSE POISONING, EMPTY THE STOMACH & INTESTINE. A. IF VICTIM IS ALERT & RESPIRATION IS NOT DEPRESSED, GIVE SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER TO INDUCE VOMITING; ADULTS (INCLUDING CHILDREN OVER 12), 30 ML; CHILDREN (UNDER 12 YR), 15 ML. CAUTION: OBSERVE VICTIM CLOSELY AFTER ADMIN IPECAC, IF CONSCIOUSNESS LEVEL DECLINES, OR IF VOMITING HAS NOT OCCURRED IN 15 MIN, PROCEED IMMEDIATELY TO INTUBATE THE STOMACH. FOLLOWING EMESIS, HAVE VICTIM DRINK A SUSPENSION OF /PRC: 30 G ACTIVATED CHARCOAL IN 3-4 OZ OF WATER (CHILDREN), 100 G IN 8-10 OZ OF WATER (ADULTS)/...TO BIND TOXICANT REMAINING IN THE GI TRACT. /CARBAMATES, CHOLINESTERASE INHIBITORS/|For more Antidote and Emergency Treatment (Complete) data for CARBANOLATE (6 total), please visit the HSDB record page.

See carbaryl. Symptomatology: 1. Nausea, vomiting, abdominal cramps, diarrhea & excessive salivation...sweating. 2. Lassitude & weakness. 3. Rhinorrhea and sensation of tightness in chest may occur with inhalation exposure. 4. Blurring or dimness of vision. Miosis...tearing, ciliary muscle spasm, loss of accommodation and ocular pain. None of these...signs...is dependable for diagnosis. Mydriasis may be seen... 5. Loss of muscle coordination, slurring of speech, fasciculation & twitching of muscles. 6. Difficulty in breathing, excessive secretions of saliva and of resp tract mucus, oronasal frothing, cyanosis, pulmonary rales & rhonchi, and hypertension. 7. ...jerky movements, incontinence, convulsions and coma. 8. Death...due to resp arrest of central origin, paralysis of resp muscles, intense bronchoconstriction or all three. /Carbaryl/

Banol

Carbanolate Use and Manufacturing

Uses

ACARICIDE, INSECTICIDE

WETTABLE POWDER 75% AI, FOR USE IN CONCENTRATE OR DIL SPRAYS. DUST--VARIABLE CONCN PREPD UPON REQUEST.

Quaternary ammonium compounds, C12-16-alkyl[(dichlorophenyl)methyl]dimethyl, chlorides: INACTIVE|SHOULD NOT BE USED WITH LIME OR OTHER ALKALINE MATERIALS. .../USED/ IN CONTROL OF INSECTS OF PLANTS & ANIMALS. HAS GOOD RESIDUAL PROPERTIES & EXCELLENT PLANT TOLERANCE. EXCELLENT CONTROL OF CHINCH BUG, COCKROACH, ETC. INTRODUCED AS ACARICIDE.|Discontinued product of The Upjohn Company.

(A) DETECTION OF RESIDUES BY GAS CHROMATOGRAPHY AFTER HYDROLYSIS & CHLOROACETYLATION. ARGAUER RJ; J AGRIC FOOD CHEM 17: 888-92 (1962). (B) GAS CHROMATOGRAPHY. WHEELER L & STROTHER A; J CHROMATOGR 45: 362-70 (1969).|GLC METHOD /FOR DETERMINATION OF CARBANOLATE/...IN APPLES, CABBAGE, COLLARDS, CORN KERNELS, GREEN BEANS, KALE, & TURNIP TOPS. RESIDUES MAY BE DETERMINED AT LEVELS OF APPROXIMATELY 0.05 PPM.|TLC: FINOCCHIARO JM & WR BENSON; J ASSOC OFFIC ANAL CHEM 50: 895 (1967). GLC: 14.3, 3.2. STROTHER, ALLEN,;J GAS CHROMATOG 6: 111 (1968).|GENERAL SAMPLE, GAS CHROMATOGRAPHY; ZWEIG, GUNTER; ANALYTICAL METHODS FOR PESTICIDES, PLANT GROWTH REGULATORS, & FOOD ADDITIVES, ACADEMIC PRESS NY NY 1 (5): 207-10 (1964).|For more Analytic Laboratory Methods (Complete) data for CARBANOLATE (7 total), please visit the HSDB record page.

Computed Properties

Molecular Weight:213.66
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:213.0556563
Monoisotopic Mass:213.0556563
Topological Polar Surface Area:38.3
Heavy Atom Count:14
Complexity:210
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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