| Cymoxanil Basic information |
| Description Physical Properties Toxicity Absorption, Distribution and Excretion Uses References |
| Product Name: | Cymoxanil |
| Synonyms: | MANEX C-8;CIMOXPRON;CYMOXANIL;CURZATE;CURZATE(R);DPX 3217;cymoxyanil;dpx3217m |
| CAS: | 57966-95-7 |
| MF: | C7H10N4O3 |
| MW: | 198.18 |
| EINECS: | 261-043-0 |
| Product Categories: | FUNGICIDE;57966-95-7 |
| Mol File: | 57966-95-7.mol |
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| Cymoxanil Chemical Properties |
| Melting point | 160-161° |
| Boiling point | 335.48°C (rough estimate) |
| density | 1.3841 (rough estimate) |
| vapor pressure | 1.5 x 10-4 Pa (20 °C) |
| refractive index | 1.6700 (estimate) |
| Fp | 100 °C |
| storage temp. | 0-6°C |
| solubility | DMSO: 100 mg/mL (504.59 mM) |
| pka | 9.7 |
| Water Solubility | 890 mg l-1 (pH 5), 780 mg l-1 (pH 7), unstable at pH 9 at 20 °C |
| form | neat |
| color | White to Light yellow to Light orange |
| Merck | 14,2765 |
| BRN | 2214018 |
| LogP | 0.590 |
| CAS DataBase Reference | 57966-95-7(CAS DataBase Reference) |
| NIST Chemistry Reference | Acetamide, 2-cyano-n-[(ethylamino)carbonyl]-2-(methoxyimino)-(57966-95-7) |
| EPA Substance Registry System | Cymoxanil (57966-95-7) |
| Safety Information |
| Hazard Codes | Xn;N,N,Xn |
| Risk Statements | 22-43-50/53 |
| Safety Statements | 36/37-60-61 |
| RIDADR | UN 3077 |
| WGK Germany | 3 |
| RTECS | AB5957000 |
| HazardClass | 9 |
| PackingGroup | III |
| HS Code | 29269090 |
| Hazardous Substances Data | 57966-95-7(Hazardous Substances Data) |
| Toxicity | For 80% formulations, LD50 orally in male rats: 1425 mg/kg; dermally in male rabbits: >3000 mg/kg. LC50 orally in bobwhite quails, mallard ducks: 2847, >10000 ppm. LC50 (96 hr) in bluegill sunfish, rainbow trout (ppm): 13.5, 18.7 (Klopping, Delp). |
| Cymoxanil Usage And Synthesis |
| Description | Cymoxanil was first introduced in 1977. It is an acetimide compound used as both a curative and preventative foliar fungicide. In Europe it is being sold for use on grapes, potatoes, tomatoes, hops, sugarbeets and other vegetable crops. Cymoxanil is currently not registered in the U.S. Cymoxanil is a fungicide used on crops including potatoes, tomatoes, and grapes. Cymoxanil is not registered for non-crop use in any country. Cymoxanil’s mode of action is as a local systemic. It penetrates rapidly and when inside the plant, it cannot be washed off by rain. It controls diseases during the incubation period and prevents the appearance of damage on the crop. The fungicide is primarily active on fungi belonging to the Peronosporales order: Phytophthora, Plasmopara, and Peronospora. |
| Physical Properties | Technical cymoxanil is a peach colored crystalline, odorless solid. |
| Toxicity | Technical cymoxanil has low acute toxicity. The acute oral LD50 is 960 mg/kg in rats. The acute dermal LD50 is >2,000 mg/kg in rabbits. The 4-hour rat inhalation LC50 is >5.06 mg/L. Minimal transient irritation of the skin and eyes was observed in rabbits. Cymoxanil did not cause skin sensitization in guinea pigs. Cymoxanil should be classified as Toxicity Category III for oral and dermal toxicity and Toxicity Category IV for inhalation toxicity and skin and eye irritation potential. Absorption, Distribution and Excretion Cymoxanil is rapidly absorbed and maximum concentrations in the blood and plasma is reached within 4 hours after dosing. Rapid and almost complete elimination of the administered radioactive dose was observed in urine and feces within 48 hours. Excretion is primarily by urine (64-75%), fecal (16-24%) and expired air (< 5%) of the administered dose. There is no significant difference in residue profiles or elimination rates between sexes, dose levels, or single or multiple dosing. No evidence of bioaccumulation was detected. DPX-T3217 is metabolized extensively and only trace level of the administered (14)C-cymoxanil was detected in the urine and feces. |
| Absorption, Distribution and Excretion | Cymoxanil is rapidly absorbed and maximum concentrations in the blood and plasma is reached within 4 hours after dosing. Rapid and almost complete elimination of the administered radioactive dose was observed in urine and feces within 48 hours. Excretion is primarily by urine (64-75%), fecal (16-24%) and expired air (< 5%) of the administered dose. There is no significant difference in residue profiles or elimination rates between sexes, dose levels, or single or multiple dosing. No evidence of bioaccumulation was detected. DPX-T3217 is metabolized extensively and only trace level of the administered (14)C-cymoxanil was detected in the urine and feces. |
| Uses | Efficient fungicide |
| References | 1. http://pmep.cce.cornell.edu/profiles/extoxnet/carbaryl-dicrotophos/cymoxanil-ext.html 2. https://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+112-31-2 3. http://www.agchemaccess.com/Cymoxanil |
| Description | Cymoxanil is a cyanoacetamide fungicide. It inhibits the mycelial growth of 12 isolates of P. infestans with EC50 values of 0.27-0.57 μg/ml. Cymoxanil (5-100 mg/l) inhibits the growth of several strains of S. cerevisiae (IC50s = 8-25 mg/l) but not S. pombe, K. marxianus, P. anomala, or C. utilis. A spray application of cymoxanil (1 mg/mL) one day after inoculation of potato leaves with P. infestans and cucumber leaves with P. cubensis reduces blighted leaves by 79 and 60%, respectively. It is toxic to rats with an acute LD50 value of 3.8 mmol/kg. Formulations containing cymoxanil have been used to prevent fungal growth on crops and treat late potato blight in agriculture. |
| Chemical Properties | A white to peach (pale pink) crystalline solid. |
| Uses | Cymoxanil is a fungicide applied as a seed treatment or as a foliar application to the plants to control late blight. |
| Uses | Agricultural fungicide. |
| Uses | Cymoxanil is a foliar applied fungicide which provides preventive and curative control of pathogen species of the order Peronosporales (eg. Phytophthora, Plasmopara and Peronospora) in grapes, potatoes, tomatoes, hops, tobacco and cucurbits. |
| Definition | ChEBI: A member of the class of ureas that is urea in which the two nitrogen atoms are substituted by an ethyl group and a 2-cyano-2-(methoxyimino)acetyl group respectively. A fungicide used to control Peronosporales on a range of crops including vin s, hops and potatoes. |
| Agricultural Uses | Fungicide: Cymoxanil is applied as a seed treatment to cut potato seed pieces or as a foliar to control late blight. |
| Trade name | CURZATE®; DPX 3217®; DPX 3217 M®; DPX-T3217®; EVOLVE®; MZ-CURZATE®; TANOS® Cymoxanil |
| Contact allergens | Cymoxanil, an urea derivative, is included (10%) with dithianone (25%) in Aktuan?. It is a fungicide agent, possibly sensitizing agricultural workers |
| Potential Exposure | Cymoxanil is a cyanoacetamide oxime fungicide applied as a seed treatment to cut potato seed pieces or as a foliar to control late blight. |
| Metabolic pathway | Cymoxanil is rapidly degraded in neutral to alkaline aqueous solutions and is metabolised extensively in soil, plants and animals. Cymoxanil degradation follows a series of cyclisation and /or hydrolysis reactions to form 5- and 6-membered ring compounds and shorter chain keto acids and amides. In plants and animals, cymoxanil is metabolised to form natural products, especially glycine. |
| Metabolism | Animals Radiolabeled cymoxanil is metabolized in the goat to natural products, including fatty acids, glycerol, glycerin, and other amino acids, lactose, and acid-hydrolysable formyl and acetyl groups. Plants Rapid degradation to naturally occurring amino acids, particularly to glycine, with subsequent incorporation into constituent sugars, starch, fatty acids, and lignin (6). Soil In laboratory soils, DT50 0.75–1.5 d (5 soils, pH range 5.7–7.8, o.m. 0.8–3.5%). In the field, DT50 (bare soil) 0.9–9 d. |
| Shipping | UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz- ardous material, Technical Name Required. |
| Degradation | The hydrolysis of cymoxanil is pH dependent. It degraded rapidly in alkaline solution at 25 °C with calculated DT50 values at pH 5,7 and 9, of 148 days, 34 hours and 31 minutes, respectively (PM). The principal hydrolysis products at pH 9 were 1-ethyldihydro-dimino-2,4,5(3H)- pyrimidinetrione 5-(O-methyloxime) (2), cyano(methoxyimino)acetic acid (3) and [[(ethylamino)carbonyl]amino]oxoacetic acid (4). Oxalic(5) and aminooxoacetic acid (6) were recovered as minor products. The principal degradation products at pH 7 were compounds 2 and 4. No hydrolytic products at pH 5 exceeded 10% of the applied radioactivity throughout the 30-day incubation (Lawler, 1996). Photolysis of cymoxanil occurred rapidly at pH 5 when irradiated under a xenon arc light source. The DT50 values of cymoxanil at 25 °C were 1.8 and 148 days, light exposed vs. dark control, respectively. 3-Ethyl-4- (methoxyamino)-2,5-dioxo-4-imidazolidinecarbonitrile(7) and 1-ethyl-imidazolidinetrione 5-(O-methyloxime) (8) were the major degradation products. Compounds 2, 4, 6 and ethylimidazolidinetrione (9) were also present as minor products (Anderson et al., 1993). The hydrolytic degradation and photolytic degradation pathways of cymoxanil are presented in Scheme 1. |
| Environmental considerations | Oral LD50 for bobwhite quail and mallard ducks >2,250 mg/kg. Eight-day dietary LC50 for bobwhite quail and mallard ducks >5,620 mg/kg diet. Fish LC50 (in mg/L at 96 h): rainbow trout 61, bluegill sunfish 29, common carp 91, Zebra fish >47.5 mg/L. Earthworm LC50 (14 d) >2,208 mg/kg soil. Daphnia magna LC50 (48 h) 27 mg/L. Algal growth inhibition LC50 (72 h) 5.2 mg/L. Honeybee contact LD50 >25 μg/bee. |
| Toxicity evaluation | Rat oral LD50: 960 mg/kg, mouse oral LD50: 860 mg/kg. Rabbit dermal LD50: >2,000 mg/kg. Mild eye irritant to rabbit (clears at 48 h). Mild, transient dermal irritation to rabbit (clears at 48 h). Inhalation LC50 (4 h) for male and female rats >5.06 mg/L. Nononcogenic and nonteratogenic. |
| Incompatibilities | Slowly hydrolyzes in water, releasing ammonia and forming acetate salts. Light sensitive. |
| Waste Disposal | Do not discharge into drains or sewers. Burn in incinerator specifically designed for pes- ticide disposal or dispose as a Hazardous waste in a landfill approved and licensed for the disposal of pesticides. Consult with environmental regulatory agencies for guid- ance on acceptable disposal practices. Ultimate disposal of the chemical must consider: the material’s impact on air quality; potential migration in soil or water; effects on ani- mal, aquatic, and plant life; and conformance with environ- mental and public health regulations. |
| Cymoxanil Preparation Products And Raw materials |
| Raw materials | Acetic anhydride–>Urea–>Acetamide–>Cyanoacetic acid–>Ethylurea |