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57966-95-7

Basic Information
CAS No.: 57966-95-7
Name: Cymoxanil
Article Data: 9
Molecular Structure:
Molecular Structure of 57966-95-7 (Cymoxanil)
Formula: C7H10N4O3
Molecular Weight: 198.181
Synonyms: 2-Cyano-N-(ethylaminocarbonyl)-2-(methoxyimino)acetamide;2-Cyano-N-ethylcarbamoyl-2-methoxyiminoacetamide;Aktuan;Curzate;DPX 3217;DPX 3217M;Tosca MZ;Cymoxanil;CURZATE;
EINECS: 261-043-0
Density: 1.27 g/cm3
Melting Point: 160-161oC
Boiling Point: 335.48°C (rough estimate)
Flash Point: 100 °C
Solubility: 890 mg l-1 (pH 5), 780 mg l-1 (pH 7), unstable at pH 9 at 20 °C
Appearance: White crystal
Hazard Symbols: HarmfulXn, DangerousN
Risk Codes: 22-43-50/53
Safety: 36/37-60-61
Transport Information: UN 3077
PSA: 103.58000
LogP: 0.13988
Synthetic route
41078-09-5

1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea

77-78-1

dimethyl sulfate

57966-95-7

2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide

Conditions
ConditionsYield
With sodium hydrogencarbonate at 50 - 70℃;
41078-06-2

2-cyano-N-(ethylcarbamoyl)acetamide

57966-95-7

2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNO2 / acetonitrile / 45 °C
2: aq. NaHCO3 / 50 - 70 °C
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Uses

 Cymoxanil is a fungicide applied as a seed treatment or as a foliar application to the plants to control late blight.


 

Toxicity Data With Reference

 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 skin > 3gm/kg (3000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A102, Pg. 1986,
dog LDLo oral 1500mg/kg (1500mg/kg)   National Technical Information Service. Vol. OTS0570815,
dog LDLo oral 1500mg/kg (1500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. OTS0570815,
guinea pig LD50 oral 1096mg/kg (1096mg/kg)   Pesticide Manual. Vol. 9, Pg. 206, 1991.
rabbit LD50 skin > 3gm/kg (3000mg/kg)   Defense des Vegetaux. Vol. 35, Pg. 179, 1981.
rat LCLo inhalation 4980mg/m3/4H (4980mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. OTS0533649-1,
rat LD50 intraperitoneal 166mg/kg (166mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0555067,
rat LD50 oral 1100mg/kg (1100mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C90, 1991.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

 

Safety Info
RTECS: AB5957000
Safety Statements: S36/37-S60-S61
HS Code: 2926909038
RIDADR: UN 3077
Risk Statements: R22; R43; R50/53
Hazard Codes: Xn

 

Specification

The IUPAC name of Cymoxanil is (1E)-2-(ethylcarbamoylamino)-N-methoxy-2-oxoethanimidoyl cyanide. With the CAS registry number 57966-95-7, it is also named as 2-Cyano-N-((ethylamino)carbonyl)-2-(methoxyimino)acetamide. The classification codes are Agricultural Chemical and Fungicide, bactericide, wood preservative. It is white crystal that the solubility at 25 °C is as follows: acetone 10.5%, dimethylformamide 18.5%, chloroform 10.3%, methanol 4.1%, benzene 0.2%, hexane 0.1%, water 0.1%. When heated to decomposition it emits toxic vapors of NOx. Additioanlly, this chemical should be stored at the temperature of 0-6 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 0.67; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.21; (4)ACD/LogD (pH 7.4): -1.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 7.25; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 7; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.537; (13)Molar Refractivity: 48.6 cm3; (14)Molar Volume: 155.5 cm3; (15)Polarizability: 19.26×10-24 cm3; (16)Surface Tension: 46.6 dyne/cm; (17)Rotatable Bond Count: 3; (18)Tautomer Count: 5; (19)Exact Mass: 198.07529; (20)MonoIsotopic Mass: 198.07529; (21)Topological Polar Surface Area: 104; (22)Heavy Atom Count: 14; (23)Complexity: 301.

Preparation of Cymoxanil: N-Ethylurea, cyanoacetic acid and acetic anhydride react to get N-cyanide acetoxy-N-ethylurea. N-cyanide acetoxy-N-ethylurea reacts with sodium nitrite to obtain 2-cyano-2-oximido-acetamide sodium salt. Then slowly adding dimethyl sulfate to 2-cyano-2-oximido-acetamide sodium salt, and continuing to adjust pH with the 50% NaOH solution. The reaction reacts at the pH value of 7-8 to get Cymoxanil.

Uses of Cymoxanil: It is an effective fungicide. It is used to control the downy mildew and late blight of tomato, cucumber, grape and other crops.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. And it may cause sensitization by skin contact. If you want to contact this product, you must wear suitable protective clothing and gloves. This material and its container must be disposed of as hazardous waste. Avoid release to the environment. Refer to special instructions / safety data sheets. 

People can use the following data to convert to the molecule structure.
1. SMILES:N#CC(=NOC)C(=O)NC(=O)NCC
2. InChI: InChI=1/C7H10N4O3/c1-3-9-7(13)10-6(12)5(4-8)11-14-2/h3H2,1-2H3,(H2,9,10,12,13) 
3. InChIKey:XERJKGMBORTKEO-UHFFFAOYAJ

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 skin > 3gm/kg (3000mg/kg)   "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc of Chemistry, 1983-86Vol. A102, Pg. 1986,
dog LDLo oral 1500mg/kg (1500mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. OTS0570815,
guinea pig LD50 oral 1096mg/kg (1096mg/kg)   Pesticide Manual. Vol. 9, Pg. 206, 1991.
rabbit LD50 skin > 3gm/kg (3000mg/kg)   Defense des Vegetaux. Vol. 35, Pg. 179, 1981.
rat LCLo inhalation 4980mg/m3/4H (4980mg/m3) BEHAVIORAL: GENERAL ANESTHETIC

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Technical Information Service. Vol. OTS0533649-1,
rat LD50 intraperitoneal 166mg/kg (166mg/kg) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE
National Technical Information Service. Vol. OTS0555067,
rat LD50 oral 1100mg/kg (1100mg/kg)   Farm Chemicals Handbook. Vol. -, Pg. C90, 1991.