57966-95-7

Basic information

• Product Name: Cymoxanil
• Synonyms: MANEX C-8;CIMOXPRON;CYMOXANIL;CURZATE;CURZATE(R);DPX 3217;2-CYANO-N-[(ETHYLAMINO)CARBONYL]-2-(METHOXYIMINO)ACETAMIDE;1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea
• CAS NO: 57966-95-7
• Molecular Formula: C₇H₁₀N₄O₃
• Molecular Weight: 198.18
• EINECS: 261-043-0
• Product Categories: FUNGICIDE
• Mol File: 57966-95-7.mol

Chemical Properties

• Melting Point: 160-161°
• Boiling Point: 335.48°C (rough estimate)
• Flash Point: 100 °C
• Appearance: White crystal
• Density: 1.3841 (rough estimate)
• Vapor Pressure: 1.5 x 10-4 Pa (20 °C)
• Refractive Index: 1.6700 (estimate)
• Storage Temp.: 0-6°C
• PKA: 9.7
• Water Solubility: 890 mg l-1 (pH 5), 780 mg l-1 (pH 7), unstable at pH 9 at 20 °C
• Merck: 14,2765
• BRN: 2214018
• CAS DataBase Reference: Cymoxanil(CAS DataBase Reference)
• NIST Chemistry Reference: Cymoxanil(57966-95-7)
• EPA Substance Registry System: Cymoxanil(57966-95-7)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 22-43-50/53
• Safety Statements: 36/37-60-61
• RIDADR: UN 3077
• WGK Germany: 3
• RTECS: AB5957000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 57966-95-7(Hazardous Substances Data)

Usage

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.

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+

Synthetic route

1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea (41078-09-5) + dimethyl sulfate (77-78-1) → 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide (57966-95-7)

Conditions	Yield
With sodium hydrogencarbonate at 50 - 70℃;

2-cyano-N-(ethylcarbamoyl)acetamide (41078-06-2) → 2-cyano-N-[(ethylamino)carbonyl]-2-(methoxyimino)acetamide (57966-95-7)

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

Upstream product

• 41078-09-5 1-(2-cyano-2-hydroxyiminoacetyl)-3-ethylurea 
• 77-78-1 dimethyl sulfate 
• 74-87-3 methylene chloride 
• 41078-06-2 2-cyano-N-(ethylcarbamoyl)acetamide 

Downstream Products

• 57012-86-9 1-ethyl-2,4,5-trioxoimidazolidine 
• 89188-25-0 acetylamino-cyano-acetic acid 
• 71342-67-1 1-ethyl-5-methoxyimino-2,4-dioxoimidazolidine 
• 1055979-74-2 1-(2,2-dimethyl-5-oxo-4-cyano-3-imidazolin-1-yl)-N-ethyl amide 

Relevant articles and documents

Improved cymoxanil synthesis method

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 Combinations Of Active Ingredients

The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, 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.

Synergistic Active Compound Combinations Comprising Phenyltriazoles

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.

On the stereochemistry of the synthesis of 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea and its E-configuration crystal structure

The synthesis of 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea leads to only one of the two possible diastereomers, which has been found to be in the E-configuration by X-ray analysis.

Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives

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.

Use of aminoisothiazoles as microbicides

PCT No. PCT/EP97/06854 Sec. 371 Date Jun. 16, 1999 Sec. 102(e) Date Jun. 16, 1999 PCT Filed Dec. 9, 1997 PCT Pub. No. WO98/27816 PCT Pub. Date Jul. 2, 1998Aminoisothiazoles of the formula I, where R is hydrogen or C1-C4 alkyl and X is halogen, NO2, CN or SCN, and metal complexes and acid addition salts thereof are used as microbicides for protecting industrial materials from being attacked and destroyed by microorganisms.

Fluoropyrazole-biphenylamide fungicides

PCT No. PCT/EP98/04663 Sec. 371 Date Feb. 10, 2000 Sec. 102(e) Date Feb. 10, 2000 PCT Filed Jul. 25, 1998 PCT Pub. No. WO99/09013 PCT Pub. Date Feb. 25, 1999The invention relates to biphenylamides having general formula (I), and their salts, in which R1 is H or F; R2 is H, halogen, alkyl, halogen methyl, alkoxy, alkylthio; R3 is CH3, CHF2, CF3. The invention also relates to agents containing biphenylamnides, the production of biphenylamides and their use in combating parasitic fungus.