57966-95-7 Usage
Description
Cymoxanil, first introduced in 1977, is a cyanoacetamide fungicide belonging to the class of ureas. It is a peach-colored crystalline, odorless solid that inhibits the mycelial growth of various pathogenic fungi. Cymoxanil is used as both a curative and preventative foliar fungicide, providing control over diseases during the incubation period and preventing damage to crops. Its mode of action is as a local systemic, meaning it penetrates rapidly and cannot be washed off by rain once inside the plant. It is primarily active against fungi belonging to the Peronosporales order, such as Phytophthora, Plasmopara, and Peronospora.
Uses
Used in Agricultural Industry:
Cymoxanil is used as a fungicide for controlling Peronosporales on a range of crops, including grapes, hops, and potatoes. It is applied as a seed treatment to cut potato seed pieces or as a foliar application to provide preventive and curative control of pathogen species.
Cymoxanil is used as an efficient fungicide for controlling late blight in agricultural crops. It is applied as a seed treatment or as a foliar application to the plants, ensuring the protection of crops like potatoes, tomatoes, and grapes from pathogenic fungi.
In addition to its use as a fungicide, Cymoxanil has been found to inhibit the growth of several strains of Saccharomyces cerevisiae, but not other yeast species such as Schizosaccharomyces pombe, Kluyveromyces marxianus, Pichia anomala, or Candida utilis. This selective activity against certain yeast strains may have potential applications in other industries, such as the food and beverage industry, for controlling yeast growth in specific contexts.
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.
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
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.
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.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 57966-95-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,9,6 and 6 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 57966-95:
(7*5)+(6*7)+(5*9)+(4*6)+(3*6)+(2*9)+(1*5)=187
187 % 10 = 7
So 57966-95-7 is a valid CAS Registry Number.
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)/b11-5+
57966-95-7Relevant articles and documents
Improved cymoxanil synthesis method
-
Paragraph 0027; 0028, (2017/05/18)
The invention discloses an improved cymoxanil synthesis method. Wastewater in the process can be recycled, so that the environmental protection pressure is greatly reduced; therefore, the improved cymoxanil synthesis process is high in yield, high in quality, environment-friendly, safe and more suitable for industrial production.
Synergistic Active Compound Combinations Comprising Phenyltriazoles
-
, (2011/07/29)
The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives
-
, (2008/06/13)
Pyrimidine compounds I wherein X is C(CO2CH3)═NOCH3, C(CONHCH3)═NOCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═CHCH3or N(CO2CH3)—OCH3; R1, R2are hydrogen, alkyl, haloalkyl or alkoxy; A is R3is hydrogen, alkyl, haloalkyl, phenoxyalkyl, cycloalkyl, cyano, alkoxy, hydroxyl or halogen; R4is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, cycloalkyl or alkoxy; Y is hydrogen, hydroxyl, halogen, optionally substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, or their salt, their synthesis and intermediates therefore, and their activity against fungi or animal pests.
