| Identification | More | [Name]
Cymoxanil | [CAS]
57966-95-7 | [Synonyms]
1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea
2-CYANO-N-[(ETHYLAMINO)CARBONYL]-2-(METHOXYIMINO)ACETAMIDE
CIMOXPRON
CURZATE
CURZATE(R)
CYMOXANIL
DPX 3217
MANEX C-8
PULSAN
RIFLE XG
2-Cyano-2-methoxyimino-N-(ethylcarbamoyl)-acetamide
2-cyano-n-((ethylamino)carbonyl)-2-(methoxyimino)-acetamid
2-cyano-n-(ethylcarbamoyl)-2-(methoxyimino)acetamide
2-cyano-n-[(ethylamino)carbonyl]-2-(methoxyimino)-acetamid
cymoxyanil
dpx3217m
int-3217-49
1-Cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide
CYMOXANIL PESTANAL (1-(2-CYANO-2-METHOX
CYMOXANIL, 100MG, NEAT | [EINECS(EC#)]
261-043-0 | [Molecular Formula]
C7H10N4O3 | [MDL Number]
MFCD00137381 | [Molecular Weight]
198.18 | [MOL File]
57966-95-7.mol |
| Chemical Properties | Back Directory | [Appearance]
A white to peach (pale pink) crystalline solid. | [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) | [form ]
neat | [pka]
9.7 | [Water Solubility ]
890 mg l-1 (pH 5), 780 mg l-1 (pH 7),
unstable at pH 9 at 20 °C | [color ]
White to Light yellow to Light orange | [Merck ]
13,2794 | [BRN ]
2214018 | [Contact allergens]
Cymoxanil, an urea derivative, is included (10%) with dithianone (25%) in Aktuan®. It is a fungicide agent, possibly sensitizing agricultural workers | [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]
57966-95-7(EPA Substance) |
| Hazard Information | Back Directory | [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. | [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. | [First aid]
f 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 and induce vomiting. Do not make an unconscious
person vomit. Evaluation by a qualified allergist, including
exposure history and testing, may help diagnose allergy. | [Shipping]
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous haz-
ardous material, Technical Name Required. | [Incompatibilities]
Slowly hydrolyzes in water, releasing
ammonia and forming acetate salts. Light sensitive. | [Chemical Properties]
A white to peach (pale pink) crystalline solid. | [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. | [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 | [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. | [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. |
| Safety Data | Back Directory | [Hazard Codes ]
Xn;N,N,Xn | [Risk Statements ]
R22:Harmful if swallowed.
R43:May cause sensitization by skin contact.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3077 | [WGK Germany ]
3 | [RTECS ]
AB5957000 | [HazardClass ]
9 | [PackingGroup ]
III | [HS Code ]
29269090 | [Hazardous Substances Data]
57966-95-7(Hazardous Substances Data) |
| Questions And Answer | Back Directory | [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 |
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