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CAS No.: | 57966-95-7 |
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Name: | Cymoxanil |
Article Data: | 9 |
Molecular Structure: | |
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: | Xn, N |
Risk Codes: | 22-43-50/53 |
Safety: | 36/37-60-61 |
Transport Information: | UN 3077 |
PSA: | 103.58000 |
LogP: | 0.13988 |
1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea
dimethyl sulfate
2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide
Conditions | Yield |
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With sodium hydrogencarbonate at 50 - 70℃; |
2-cyano-N-(ethylcarbamoyl)acetamide
2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide
Conditions | Yield |
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Multi-step reaction with 2 steps 1: NaNO2 / acetonitrile / 45 °C 2: aq. NaHCO3 / 50 - 70 °C View Scheme |
Cymoxanil is a fungicide applied as a seed treatment or as a foliar application to the plants to control late blight.
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. |
Safety Info | |
RTECS: | AB5957000 |
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Safety Statements: | S36/37-S60-S61 |
HS Code: | 2926909038 |
RIDADR: | UN 3077 |
Risk Statements: | R22; R43; R50/53 |
Hazard Codes: | Xn |
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. |