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Chlorflurazole

HCID 19232
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
3615-21-2
Standard SMILES
FC(F)(F)c1nc2c(Cl)c(Cl)ccc2[nH]1
InChIKey
KSROTSBULDYPKA-UHFFFAOYSA-N
Molecular formula
C8H3Cl2F3N2
Average molar mass
255.02 g/mol
Monoisotopic mass
253.962538

Overview

Benzimidazole, 4,5-dichloro-2-(trifluoromethyl)- appears as a crystalline solid. Fine white needles when pure; the commercial material is brownish. Used as an herbicide. (EPA, 1998)

Names & identifiers

Preferred name
Chlorflurazole
IUPAC
4,5-dichloro-2-(trifluoromethyl)-1H-benzimidazole
English name
4,5-dichloro-2-trifluoromethylBenzimidazole
Molecular formula
C8H3Cl2F3N2
Molecular weight
255.02

Names & synonyms

ChlorflurazoleChlorflurazole [ISO]CHLOROFLUORAZOLECaswell No. 327AHSDB 2764UNII-ZXH1IGJ511EPA Pesticide Chemical Code 327200BRN 0960437Benzimidazole, 4,5-dichloro-2-(trifluoromethyl)-CHLORFLURAZOLE [HSDB]DTXSID0041773RefChem:125313
Show more names
NC-3363CHLORFLURAZOLCHLORFLURAZOLE)Chloroflurazole.4,5-dichloro-2-(trifluoromethyl)4,5-dichloro-2-trifluoromethylBenzimidazoleBENZIMIDAZOLE,4,5-DICHLORO-2-(TRIFLUOROMETHYL)-4,5-Dichloro-2-trifluoromethyl-1H-benzimidazole4,5-dichloro-2-(trifluoromethyl)-1H-benzoimidazole1H-Benzimidazole, 6,7-dichloro-2-(trifluoromethyl)-
DTXCID80217734,5Dichloro2trifluoromethylbenzimidazole4,5Dichloro2(trifluoromethyl)benzimidazole4,5Dichloro2(trifluoromethyl)1HbenzimidazoleBenzimidazole, 4,5dichloro2(trifluoromethyl)1HBenzimidazole, 4,5dichloro2(trifluoromethyl)1-H-BENZIMIDAZOLE, 4,5-DICHLORO-2-(TRIFLUOROMETHYL)-BENZIMIDAZOLE, 4,5(OR 6,7)-DICHLORO-2-(TRIFLUOROMETHYL)-

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
28.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
0
Heavy atoms
15
Formal charge
0
Complexity
249

Experimental & physicochemical properties

PesticidesPesticides -> Herbicides, Other
LogP · 2 items

3.49

3.49

Density3.49 @25 °C
Color/FormCRYSTALLINE SOLID, FORMING FINE WHITE NEEDLES WHEN PURE.
Solubility69 PPM IN WATER @ 25 °C; SPARINGLY SOL IN METHYL NAPHTHALENE & BENZENE; SOL UP TO 25% IN ETHANOL, ETHER, CHLOROFORM, PROPYLENE GLYCOL, GLYCEROL FORMAL, METHYL NAPHTHALENE; VERY SOL IN ACETONE.
Flash Point(Non-Specific -- Pesticide, solid, n.o.s.) May burn, but does not ignite readily. (EPA, 1998)
Melting Point · 2 items

415 to 417 °F (EPA, 1998)

213-214 °C

Vapor Pressure · 4 items

4e-05 mmHg at 72.5 °F (EPA, 1998)

0.0000029 [mmHg]

4X10-5 MM HG @ 22.5 °C

0.00004 [mm Hg] @22.5 °C

Physical Description · 2 items

Safety & regulation

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

Hazard information

Regulatory InformationThe 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.)
Fire Hazards · 1 item

(Non-Specific -- Pesticide, solid, n.o.s.) Fire may produce irritating or poisonous gases. Runoff from fire control or dilution water may cause pollution. Avoid amine salts of hormone herbicides, alkali-unstable fungicides or insecticides. (EPA, 1998)

Health Hazards(Non-specific -- Pesticide, solid, n.o.s.) Poisonous if swallowed. Inhalation of dust poisonous. (EPA, 1998)
Hazards SummaryModerately toxic by ingestion in animal studies; Uncouples oxidative phosphorylation in liver suspensions; [HSDB]
Reactive GroupAmines, Phosphines, and Pyridines
Reactivity Profile · 1 item

BENZIMIDAZOLE, 4,5-DICHLORO-2-(TRIFLUOROMETHYL)- is a halide- and amine-substituted aromatic compound. 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.

Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Lower Explosive Limit (LEL)May burn but does not ignite readily. (EPA, 1998)
Upper Explosive Limit (UEL)May burn but does not ignite readily. (EPA, 1998)

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 3 items

YIELDS 4,5-DICHLORO-6-HYDROXY-2-TRIFLUOROMETHYLBENZIMIDAZOLE & 4,5-DICHLORO-7-HYDROXY-2-TRIFLUOROMETHYLBENZIMIDAZOLE IN RABBIT & RAT. /FROM TABLE/

MICROSOMAL MIXED FUNCTION OXIDASES OF MOUSE LIVER HYDROXYLATED THE BENZENE MOIETY OF CHLOROFLUORAZOLE. URINE OF RATS ADMIN 1.5 MG ORALLY CONTAINED 6-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MAJOR, 7-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MINOR, & 5-HYDROXY-4,6-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE CONJUGATES MINOR.

1ST 24-HR URINARY METAB AFTER ORAL ADMIN TO RABBITS & RATS CONTAINED AFTER ACID HYDROLYSIS 7-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, 6-HYDROXY-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, & 6,7-DIOXO-4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE GLUCURONIDES & SULFATES

Absorption, Distribution and ExcretionFOLLOWING ORAL ADMIN TO RATS & RABBITS OF (14)C-LABELED 4,5-DICHLORO-2-TRIFLUOROMETHYLBENZIMIDAZOLE, (14)C WAS EXCRETED IN THE URINE IN 3 DAYS.

Uses & manufacturing

Uses · 3 items

Used as herbicide; Formerly manufactured by Fisons LTD; [HSDB]

Farming (Pesticides) [Category: Industry]

HERBICIDE

Formulations/Preparations · 1 item

CHLORFLURAZOLE 5, CONTAINING 20% OF SODIUM SALT INTENDED FOR USE ON FLAX. CHLORFLURAZOLE W, CONTAINING 20% OF SODIUM SALT & WETTING AGENT, INTENDED FOR USE ON CEREALS. MIXTURES WITH /4-CHLORO-2-METHYLPHENOXYACETIC ACID/ (MCPA) 1 LB CHLORFLURAZOLE LA; 1.5 LB CHLORFLURAZOLE LB; 2.0 LB CHLORFLURAZOLE LC; EACH CONTAINING 1 LB MCPA.

General Manufacturing Information · 3 items

FORMERLY MANUFACTURED BY FISONS LTD.

INCOMPATIBILITIES: AQUEOUS SALT FORMULATIONS ARE COMPATIBLE WITH SIMILARLY FORMULATED HORMONE WEED KILLERS & WITH TRIAZINES, BUT AMINE SALTS OF HORMONE HERBICIDES ARE NOT COMPATIBLE WITH CHLORFLURAZOLE. ... TREATMENT CAUSES SCORCHING & DRYING OUT OF SUSCEPTIBLE FOLIAGE WITHIN 2-6 DAYS. CHLORFLURAZOLE IS AN ACTIVE UNCOUPLER OF PHOSPHORYLATION IN PLANTS, & IT ALSO APPEARS TO INHIBIT THE HILL REACTION.

Related reactions

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No reaction records under the current filter.

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
3615-21-2
PubChem CID
19232
DTXSID
DTXSID0041773
UNII
ZXH1IGJ511
Nikkaji
J8.183C

Benzimidazole, 4,5-dichloro-2-(trifluoromethyl)- appears as a crystalline solid. Fine white needles when pure; the commercial material is brownish. Used as an herbicide. (EPA, 1998)

Solid (white when pure); Commercial product is brownish; [HSDB]

Stability/Shelf Life... VOLATILITY LOW ... AQUEOUS SALT FORMULATIONS ARE BELIEVED CHEMICALLY STABLE IN AIR.
Other Experimental Properties · 3 items

NO DETECTABLE HYDROLYSIS IN AQ ACID OR ALKALI & NO REACTION AT ROOM TEMP WITH NORMAL LAB OXIDIZING AGENTS.

Brownish /Commercial material/

THE 1-HYDROGEN HAS ACIDIC PROPERTIES (PKA 6.96) FORMING WATER-SOL ALKALI METAL AND AMMONIUM SALTS.

Physicochemical properties

Melting point
213.5 °C · 213.5°C
Boiling point
337.8 · 337.8±42.0 °C(Predicted)
Density
1.5776 · 1.5776 (estimate)
pka
7.34 · 7.34±0.10(Predicted)
Water Solubility
60 mg/L · 60mg/L(temperature not stated)
FDA UNII
1 IGJ511 · ZXH1IGJ511
EPA Substance Registry System
Chlorflurazole (3615-21-2)
RIDADR
2588 · 2588
HazardClass
6.1 · 6.1(a)
PackingGroup
II
Hazardous Substances Data
3615 · 3615-21-2(Hazardous Substances Data)

Safety & protection

Fire Fighting · 1 item

(Non-Specific -- Pesticide, solid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing.

First Aid · 1 item

Inhalation and ingestion are routes of entry. Non-Specific -- Pesticide, solid, n.o.s.Move victim to fresh air; call emergency medical care. Remove and isolate contaminated clothing and shoes at the site. In case of contact with material, immediately flush skin or eyes with running water for at least 15 minutes. (EPA, 1998)

Nonfire Spill Response(Non-Specific -- Pesticide, solid, n.o.s.) Do not touch spilled material; stop leak if you can do it without risk.
Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

78 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

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)

Toxicology

Non-Human Toxicity Excerpts · 1 item

NON-PHYTOTOXIC TO CEREALS. BEES EXPOSED TO SPRAY WERE UNAFFECTED BY 1000 PPM PURE CHLORFLURAZOLE AS AQUEOUS SUSPENSION OR SODIUM SALT SOLN, BUT WERE KILLED BY 4000 PPM. ... AN UNCOUPLER OF OXIDATIVE PHOSPHORYLATION CAUSING 50% UNCOUPLING OF RAT LIVER MITOCHONDRIAL OXIDATIVE PHOSPHORYLATION AT 6X10-7 MOLAR ALSO STIMULATING ATPASE ACTIVITY & CELL RESPIRATION.

Antidote and Emergency Treatment · 3 items

1. SKIN CONTAMINATION SHOULD BE REMOVED PROMPTLY BY WASHING WITH SOAP AND WATER. CONTAMINATION OF THE EYES SHOULD BE TREATED IMMEDIATELY BY PROLONGED FLUSHING OF THE EYES WITH COPIOUS AMOUNTS OF CLEAN WATER. IF DERMAL OR OCULAR IRRITATION PERSISTS, MEDICAL ATTENTION SHOULD BE OBTAINED WITHOUT DELAY. /OTHER HERBICIDES/

2. INGESTIONS OF THESE HERBICIDES ARE LIKELY TO BE FOLLOWED BY VOMITING AND DIARRHEA DUE TO THE IRRITANT PROPERTIES OF MOST OF THE TOXICANTS. ... A. IF LARGE AMOUNTS OF HERBICIDE HAVE BEEN INGESTED, AND IF THE PATIENT IS FULLY ALERT INDUCE EMESIS WITH SYRUP OF IPECAC, FOLLOWED BY SEVERAL GLASSES OF WATER. DOSAGE FOR ADULTS AND CHILDREN OVER 12 YEARS: 30 ML; DOSAGE FOR CHILDREN UNDER 12 YEARS 15 ML. WHEN VOMITING HAS STOPPED, GIVE ACTIVATED CHARCOAL. ADD SORBITOL TO THE CHARCOAL SLURRY UNLESS DIARRHEA HAS ALREADY COMMENCED. IF, FOR SOME REASON, THE PATIENT IS NOT FULLY ALERT, PUT IN PLACE A CUFFED ENDOTRACHEAL TUBE TO PROTECT THE AIRWAY, THEN ASPIRATE AND LAVAGE THE STOMACH WITH A SLURRY OF ACTIVATED CHARCOAL. LEAVE A QUANTITY OF CHARCOAL, WITH SORBITOL, IN THE STOMACH BEFORE WITHDRAWING THE STOMACH TUBE. REPEATED ADMINISTRATION OF CHARCOAL AT HALF OR MORE THE INITIAL DOSAGE EVERY 2-4 HOURS MAY BE BENEFICIAL. /OTHER HERBICIDES/

2. B. IF THE AMOUNT OF INGESTED HERBICIDES WAS SMALL, IF EFFECTIVE EMESIS HAS ALREADY OCCURRED, OR IF TREATMENT IS DELAYED, ADMINISTER THE ACTIVATED CHARCOAL AND SORBITOL BY MOUTH. C. IF SERIOUS DEHYDRATION AND ELECTROLYTE DEPLETION HAVE OCCURRED AS A RESULT OF VOMITING AND DIARRHEA, MONITOR BLOOD ELECTROLYTES AND AND FLUID BALANCE AND ADMINISTER INTRAVENOUS INFUSIONS OF GLUCOSE, NORMAL SALINE RINGER'S SOLUTION, OR RINGER'S LACTATE TO RESTORE EXTRACELLULAR FLUID VOLUME AND ELECTROLYTES. FOLLOW THIS WITH ORAL NUTRIENTS AS SOON AS FLUIDS CAN BE RETAINED. FLUIDS SERVE TO SUPPORT EXCRETION OF THE TOXICANTS. D. SUPPORTIVE MEASURES ARE ORDINARILY SUFFICIENT FOR SUCCESSFUL MANAGEMENT OF EXCESSIVE EXPOSURES TO THESE HERBICIDES. /OTHER HERBICIDES/

Safety data

ridadr
2588
hazard_class
6.1(a)
packing_group
II
Hazardous Substances Data
3615-21-2(Hazardous Substances Data)

INCOMPATIBILITIES: ON ACCOUNT OF THE ALKALINITY, AQUEOUS SALT FORMULATIONS SHOULD NOT BE MIXED WITH VERY ALKALI-UNSTABLE FUNGICIDES OR INSECTICIDES.

Applications

Descriptionchlorflurazole is an obsolete cereal herbicide. It is moderately soluble in water but little else is known about its environmental fate or ecotoxicology. it has a high mammalian oral toxicity.

General DescriptionA crystalline solid. Fine white needles when pure; the commercial material is brownish. Used as an herbicide.

Suppliers2 total

Alfa Chemistry+1-5166625404 · [email protected]
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]