Basic information
- CAS
116-52-9- Standard SMILES
O=C(NC(O)C(Cl)(Cl)Cl)NC(O)C(Cl)(Cl)Cl- InChIKey
PPJXIHLNYDVTDI-UHFFFAOYSA-N- Molecular formula
- C5H6Cl6N2O3
- Average molar mass
- 354.8 g/mol
- Monoisotopic mass
- 351.850958
Overview
structure
Names & identifiers
- Preferred name
- 1,3-Bis(2,2,2-trichloro-1-hydroxyethyl)urea
- IUPAC
- 1,3-bis(2,2,2-trichloro-1-hydroxyethyl)urea
- English name
- DCU
- Molecular formula
- C5H6Cl6N2O3
- Molecular weight
- 354.83
Names & synonyms
Dicloralurea116-52-9Dichloralurea1,3-Bis(2,2,2-trichloro-1-hydroxyethyl)ureaDICHLORAL UREACrag herbicide 2Crag DCU-73WDichloralureeDicloralureeDKhMExperimental herbicide 2Crag experimental herbicide 2
Show more names
eh2rc9485dcu[qr]eh2[qr]dkhm[qr]dichloralrc9485[qr]
1,3-Bis(1-hydroxy-2,2,2-trichloroethyl)ureaSk&F 1995DCU Crag Herbicide 2SKF 1995DTXSID00418529J3ZB93FIENSC-32207RC 9485
Database identifiers
- CAS
116-52-9- PubChem CID
- 8313
- DTXSID
DTXSID0041852- ChEMBL
CHEMBL2106294- UNII
- 9J3ZB93FIE
- EC Number
- 204-144-7
- Nikkaji
- J5.282E
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 81.6 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 228
Experimental & physicochemical properties
PesticidesPesticides -> Herbicides, Urea Derivative
Density1.63 at 25 °C
Color/FormColorless crystals
Solubility
0.0074 PPM SOL IN WATER @ 25 °C
At 25 °C: 18.8 mg/100 g ethanol, 16.8 mg/100 g acetone, 2.5 mg/100 g ether, 5.5 mg/100 g n-hexane, 3.0 mg/100 g benzene, 1.0 mg/100 g chloroform
Melting Point196 °C
Physical DescriptionColorless solid; [HSDB]
Stability/Shelf Life
STABLE TO UV LIGHT ON FILTER PAPER; THERMALLY UNSTABLE
Stable to dilute acids at room temp. Decomposed by alkalis.
Physicochemical properties
- Melting point
- 196 °C · 196 °C
- Boiling point
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
Hazards SummaryUrea-derived herbicides have low toxicity in animal feeding studies; [HSDB] Systemic toxicity unlikely unless large amounts ingested; [EPA Pesticides, p. 122] May cause irritation; [MSDSonline]
Toxicology
Interactions
TOXICITY OF MIXTURES OF TRICHLOROPROPIONITRILE (TCHP) WITH DICHLORAL UREA (DCHU) & TRICHLOROACETIC ACID (TCHA) WITH DICHLORAL UREA WERE STUDIED IN 167 WHITE RATS & CATS. THE HERBICIDE COMBINATIONS EMPLOYED ARE IN ACTUAL AGRICULTURAL USE IN WESTERN PROVINCES OF UKRAINE, ESP IN LVOV PROVINCE. ACUTE POISONING BY COMBINATIONS WAS DIFFERENT FROM THAT BY INDIVIDUAL AGENTS; TOXICITY WAS LOWERED (NO 100% MORTALITY). MORTALITY INCIDENCE WAS 18.8% FOR TCHA & DCHU (6 OF 32 ANIMALS) & FOR TCHP & DCHU, 8.3% (2 OF 24 ANIMALS). MAIN SIGNS OF POISONING FROM INDIVIDUAL HERBICIDES WERE ABSENT WITH THE MIXTURES.
Environmental Biodegradation
MICROBIAL DECOMPOSITION OF 12 & 24 MG/KG DICHLORAL UREA STARTED IMMEDIATELY AFTER IT WAS MIXED WITH MEADOW PODZOLIC SOIL OR A PODZOLIZED CHERNOZEM, & 10-12 DAYS LATER AMT OF FORMED TRICHLOROACETIC ACID WAS EQUAL TO 50% OF TRICHLOROACETIC ACID FOUND IN SOIL SAMPLES MIXED WITH SODIUM TRICHLOROACETATE IN DOSES EQUIVALENT TO DOSES OF DICHLORAL UREA.
Non-Human Toxicity Excerpts
LOW SKIN IRRITANCY. CHRONIC FEEDING IN RATS CAUSED FUNCTIONAL ALTERATIONS IN BLOOD, LIVER AND KIDNEY.
SLIGHT CYTOGENETIC EFFECT WAS FOUND IN MOUSE BONE-MARROW CELLS TREATED WITH DICHLORAL UREA.
Antidote and Emergency Treatment
1. WASH CONTAMINATED SKIN WITH SOAP & WATER. 2. FLUSH CONTAMINATED EYES WITH COPIOUS AMOUNTS OF FRESH WATER FOR 15 MINUTES. 3. INGESTIONS OF SMALL AMOUNTS (LESS THAN 10 MG/KG BODY WEIGHT) OCCURRING LESS THAN AN HOUR BEFORE TREATMENT, ARE PROBABLY BEST TREATED BY: A. SYRUP OF IPECAC, FOLLOWED BY 1-2 GLASSES OF WATER. DOSE FOR ADULTS & CHILDREN OVER 12 YEARS: 30 ML. DOSE FOR CHILDREN UNDER 12 YEARS: 15 ML. B. ACTIVATED CHARCOAL: /PRC: 30 G ACTIVATED CHARCOAL IN 3-4 OZ WATER (CHILDREN), 100 G IN 8-10 OZ WATER (ADULT)/...AFTER VOMITING STOPS. C. SODIUM OR MAGNESIUM SULFATE, 0.25 G/KG IN TAP WATER, AS A CATHARTIC. /PESTICIDES OF LOW OR MODERATE TOXICITY/
Chemistry & industry
Pharmacology
Mechanism of Action...ACCUMULATE IN LEAVES WHERE THEY CAUSE COLLAPSE OF PARENCHYMAL VESSELS. ... IN LEAVES THEY INHIBIT PHOTOSYNTHESIS...& ARE POWERFUL INHIBITORS OF OXIDATION OF WATER TO OXYGEN... /UREA HERBICIDES/
Metabolism/MetabolitesIn the intermediate stages of metab in...plants, monochlorourea and chloral are degraded to the major metabolite TCA (trichloroacetic acid). Residues in rape at harvest are less than 0.02 mg DCU/kg...
Absorption, Distribution and ExcretionSUBSTITUTED UREAS ARE READILY ABSORBED BY PLANT ROOTS & TRANSLOCATED TO ACCUMULATE IN LEAVES... HOWEVER, THEY DO NOT PENETRATE READILY THROUGH LEAVES. /UREA HERBICIDES/
Cellular LocationsCytoplasm
Uses & manufacturing
Uses
Used as pre-emergence herbicide for sugar beets, vegetables, and other crops; Union Carbide superseded product which is currently of little commercial interest; [HSDB]
Farming (Pesticides) [Category: Industry]
PREEMERGENCE HERBICIDE
Formulations/PreparationsWettable powder.
General Manufacturing Information
UNION CARBIDE SUPERSEDED PRODUCT BELIEVED TO BE CURRENTLY OF LITTLE COMMERCIAL INTEREST.
IN THE EARLY 1950'S SEVERAL SUBSTITUTED UREAS WERE DEVELOPED, THE FIRST OF WHICH, DICHLORAL UREA, ATTAINED BRIEF COMMERCIAL USE FOR THE SELECTIVE CONTROL OF WEEDS IN SUGARBEETS.
FORMERLY FOR USE ON SUGAR BEETS & CERTAIN OTHER FIELD & VEGETABLE CROPS.
Miscible with other wettable-powder herbicides.
Applications
Food additive (veterinary).
Related reactions
1 records
Compound notes
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