| Identification | Back Directory | [Name]
SIDURON | [CAS]
1982-49-6 | [Synonyms]
Trey
h1318
SIDURON
DuP-1318
TUPERSAN
dupont1318
NSC 131951
TUPERSAN(R)
UNII:513S964LJO
SIDURON, 1GM, NEAT
dupontherbicide1,318
SALOR-INT L131210-1EA
Siduron 1g [1982-49-6]
Siduron Reference Material
Siduron @100 μg/mL in MeOH
MYCLOBUTANIL PESTANAL, 100 MG
Siduron @0.1 mg/mL in Acetonitrile
1-(2-methylcyclohexyl)-3-phenyl-ure
1-(2-METHYLCYCLOHEXYL)-3-PHENYLUREA
n-(2-methylcyclohexyl)-n’-phenylurea
n-phenyl-n’-(2-methylcyclohexyl)urea
Urea, N-(2-methylcyclohexyl)-N'-phenyl- | [EINECS(EC#)]
217-844-2 | [Molecular Formula]
C14H20N2O | [MDL Number]
MFCD00072453 | [MOL File]
1982-49-6.mol | [Molecular Weight]
232.32 |
| Chemical Properties | Back Directory | [Appearance]
Colorless or white crystalline solid or powder.
Odorless. Commercial product is available as an emulsifi-
able concentrate. | [Melting point ]
135.5℃ | [Boiling point ]
374.49°C (rough estimate) | [density ]
1.0151 (rough estimate) | [refractive index ]
1.5110 (estimate) | [storage temp. ]
0-6°C | [form ]
Powder | [pka]
12.38±0.40(Predicted) | [color ]
Light gray | [Water Solubility ]
18mg/L(25 ºC) | [Merck ]
13,8561 | [BRN ]
2725940 | [Henry's Law Constant]
1.5×105 mol/(m3Pa) at 25℃, HSDB (2015) | [Major Application]
agriculture
environmental | [InChI]
1S/C14H20N2O/c1-11-7-5-6-10-13(11)16-14(17)15-12-8-3-2-4-9-12/h2-4,8-9,11,13H,5-7,10H2,1H3,(H2,15,16,17) | [InChIKey]
JXVIIQLNUPXOII-UHFFFAOYSA-N | [SMILES]
CC1CCCCC1NC(=O)Nc2ccccc2 | [CAS DataBase Reference]
1982-49-6 | [EPA Substance Registry System]
Siduron (1982-49-6) |
| Hazard Information | Back Directory | [Chemical Properties]
Colorless or white crystalline solid or powder.
Odorless. Commercial product is available as an emulsifi-
able concentrate. | [Agricultural Uses]
Herbicide: A pre-emergence herbicide used to control annual grasses, e.g., crabgrass, foxtail, and barnyard grass. Used on newly seeded or established turf and lawn grasses and as pre-emergence treatment to bare soil following spring seeding. Not listed for use in EU countries. Registered for use in the U.S. | [Trade name]
GREENFIELD®; GRO-TONE®[C]; H-1318®; TREY®; TUPERSAN® | [Potential Exposure]
A phenyl urea preemergence herbicide
used to control annual grasses (e. g., crabgrass, foxtail, and
barnyard grass) and on newly seeded or established turf
and lawn grasses and as bare soil treatment following
spring seeding. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions) if
breathing has stopped, and CPR if heart action has stopped.
Transfer promptly to a medical facility. When this chemical
has been swallowed, get medical attention. Give large
quantities of water. Do not induce vomiting when formula-
tions containing petroleum solvents are ingested. Do not
make an unconscious person vomit. | [Shipping]
UN2767 Phenyl urea pesticides, solid, toxic,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
UN3002 Phenyl urea pesticides, liquid, toxic, Hazard
Class: 6.1; Labels: 6.1-Poisonous materials. | [Description]
Siduron is a selective pre-emergence herbicide. It has a moderate aqueous solubility, is volatile and, based on its chemical properties, it is moderately mobile with has a high potential to leach to groundwater. It is persistent in both soil and water systems. It has a relatively low mammalian toxicity and would not be expected to bioaccumulate. It is classified as an irritant. It is not highly toxic to birds, is moderately toxic to fish, algae and honeybees. | [Waste Disposal]
Incinerate in a unit with efflu-
ent gas scrubbing. Containers must be disposed of properly
by following package label directions or by contacting your
local or federal environmental control agency, or by
contacting your regional EPA office. | [Uses]
Selective preemergence herbicide used to control annual weed grasses and prevent
growth of crabgrass, foxtail and barnyard grass in turf, cereals and other food crops. | [Definition]
ChEBI:Siduron is a member of ureas. | [Production Methods]
The production of siduron typically begins with the synthesis of N,N-dimethylurea, which serves as a key intermediate. This compound is then reacted with 2,3-dihydro-1H-indene-1-carbonyl chloride or a similar indanone derivative under controlled conditions to form the final siduron molecule. The reaction involves nucleophilic substitution, where the urea nitrogen attacks the carbonyl carbon of the acid chloride, forming the desired urea linkage. The process may require solvent mediation and temperature control to optimise yield and purity. | [General Description]
Siduron is a pre-emergence and post emergence phenylurea herbicide used for the control of annual grass weeds. Its mode of action involves the inhibition of photosynthesis. | [Mechanism of action]
Selective, absorbed by roots and translocated. Photosynthetic electron transport inhibitor at the photosystem II. | [Environmental Fate]
Soil. A fungus and two Pseudomonas spp. isolated from soil degraded siduron to form
the major metabolites: 1-(4-hydroxy-2-methylcyclohexyl)-3-(p-hydroxyphenyl)urea, 1-(4-
hydroxy-2-methylcyclohexyl)-3-phenylurea and 1-(4-hydroxyphenyl)-3-(2-methycyclohexyl)urea (Belasco and Langsdorf, 1969).
Plant. After 8 days following absorption in barley plants, no metabolites were detected
(Splittstoesser and Hopen, 1968). | [Pesticide Type]
Herbicide |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38-52/53 | [Safety Statements ]
26-61 | [RIDADR ]
UN3077 (solid); UN3082(liquid) | [WGK Germany ]
2 | [RTECS ]
YT7350000 | [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids | [Hazardous Substances Data]
1982-49-6(Hazardous Substances Data) | [Toxicity]
LC50 (48-hour) for carp 18 mg/L and Japanese goldfish 10–40 mg/L (Worthing
and Hance, 1991); acute oral LD50 for rats >7,500 mg/kg (Ashton and Monaco, 1991),
5,000 mg/kg (RTECS, 1985). |
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