Myclobutanil

Names

[ Name ]:
Myclobutanil

[Synonym ]:
1H-1,2,4-Triazole-1-propanenitrile, α-butyl-α-(4-chlorophenyl)-
α-Butyl-α-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile
Systhane Technical
rac-(2R)-2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
2-(4-Chlorphenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanonitril
Synthane 12E
2-(4-Chlorophényl)-2-(1H-1,2,4-triazol-1-ylméthyl)hexanenitrile
Nova W
2-(4-chlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)hexanenitrile
2-(4-Chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
Systhane
Systhane 6 Flo
a-Butyl-a-(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile
Rally
(RS)-2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile
MFCD00144818
T5NN DNJ A1X4&CN&R DG
Myclobutanil

Biological Activity

[Description]:

Myclobutanil is a conazole class fungicide widely used as an agrichemical.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Infection

[In Vitro]

Myclobutanil reduces cell viability to <50% at 100 ppm and to <10% at 500 ppm. Myclobutanil promotes a slight, but significant, increase in fatty acid (FA)-induced steatotosis at doses from 1 to 100 ppm. Anti-apoptotic biomarkers are significantly reduced by Myclobutanil[1].

[Kinase Assay]

To further evaluate apoptosis, cell extracts are collected after 24 h of exposure to Myclobutanil, centrifuged, and analyzed with a multiplex biometric ELISA-based immunoassay containing dyed microspheres conjugated to a monoclonal antibody specific for the target protein. Apoptosis biomarkers are BCL-xL/Bak dimer and Mcl-1/Bak dimer, quantified using RBM Apoptosis Panel 3. Each experiment is performed in triplicate and apoptosis biomarker levels determined using the Bio-Plex Array Reader. The analytic concentrations are calculated using a standard curve, according to the manufacturer’s instructions[1].

[Cell Assay]

The hepatoma cell line HepG2 is used in this study. The cells are grown on tissue culture plates in an incubator with a humidified atmosphere (95% air/5% CO2 v/v) at 37°C. Steatosis is induced by incubating the hepatocytes with 6 mM of a 1:1 v/v mixture of oleic (18:1) and linoleic (18:2) fatty acids (Fas) for 24 h. After a wash with PBS, cells are exposed for an additional 24 h to Myclobutanil at 0.1, 1, 10, 100 or 500 ppm. Cytotoxicity is assessed in HepG2 cells (1.0×105 cells/well in 24-well plates) by measuring the reduction of the tetrazolium dye 3-(4, 5-dimethylthiazol-2-yl)-5-(3carboxymethoxyphenyl)-2-(4-sulfophenyl)-2H-tetrazolium (MTT)[1].

[References]

[1]. Stellavato A, et al. Myclobutanil worsens nonalcoholic fatty liver disease: An in vitro study of toxicity and apoptosis on HepG2 cells. Toxicol Lett. 2016 Nov 16;262:100-104.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
465.2±55.0 °C at 760 mmHg

[ Melting Point ]:
63-68°C

[ Molecular Formula ]:
C₁₅H₁₇ClN₄

[ Molecular Weight ]:
288.775

[ Flash Point ]:
235.2±31.5 °C

[ Exact Mass ]:
288.114166

[ PSA ]:
54.50000

[ LogP ]:
2.82

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.589

[ Storage condition ]:
0-6°C

[ Water Solubility ]:
142 mg/L (25 ºC)

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ5257000

CHEMICAL NAME :: 1H-1,2,4-Triazole-1-propanenitrile, alpha-butyl-alpha-(4-chlorophenyl)-

CAS REGISTRY NUMBER :: 88671-89-0

LAST UPDATED :: 199710

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C15-H17-Cl-N4

MOLECULAR WEIGHT :: 288.81

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PEMNDP Pesticide Manual. (The British Crop Protection Council, 20 Bridport Rd., Thornton Heath CR4 7QG, UK) V.1- 1968- Volume(issue)/page/year: 9,601,1991

TYPE OF TEST :: LC50 - Lethal concentration, 50 percent kill

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/m3

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FMCHA2 Farm Chemicals Handbook. (Meister Pub., 37841 Euclid Ave., Willoughy, OH 44094) Volume(issue)/page/year: -,C291,1991

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2229 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: DEVEAA Defense des Vegetaux. (Federation Nationale des Groupements de Protection des Cultures, 149, rue de Bercy, 75595 Paris Cedex, 12, France) V.1- 1947- Volume(issue)/page/year: 40(242),9,1986

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - other glands

REFERENCE :: NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: OTS0570641

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 7500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: PBCDDQ Proceedings-British Crop Protection Conference-Pests and Diseases. (British Crop., Protection Council, 2A Kidderminster Rd., Croydon, CRO 2UE, UK) 1977- Volume(issue)/page/year: -,55,1986

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319-H361d-H411

[ Precautionary Statements ]:
P273-P281-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R36;R51/53;R63

[ Safety Phrases ]:
S36/37-S46-S61

[ RIDADR ]:
UN 3077

[ RTECS ]:
XZ5257000

[ HS Code ]:
2933990015

Customs

[ HS Code ]: 2933990015

[ Summary ]:
2933990015 3-((1h-1,2,4-triazol-1-yl)methyl)-1-(4-chlorophenyl)-4,4-dimethylpentan-3-ol。supervision conditions:s(import or export registration certificate for pesticides)。VAT:17.0%。tax rebate rate:9.0%。MFN tarrif:6.5%。general tariff:20.0%

Articles

The effects of the fungicides fenhexamid and myclobutanil on SH-SY5Y and U-251 MG human cell lines.

Environ. Toxicol. Pharmacol. 38(3) , 968-76, (2014)

Mixtures of pesticides in foodstuffs and the environment are ubiquitous in the developed world and although agents are usually exhaustively tested individually, the toxicological implications of pesti...

Triazole fungicides can induce cross-resistance to medical triazoles in Aspergillus fumigatus.

PLoS ONE 7(3) , e31801, (2012)

Azoles play an important role in the management of Aspergillus diseases. Azole resistance is an emerging global problem in Aspergillus fumigatus, and may develop through patient therapy. In addition, ...

Acaricide, fungicide and drug interactions in honey bees (Apis mellifera).

PLoS ONE 8(1) , e54092, (2013)

Chemical analysis shows that honey bees (Apis mellifera) and hive products contain many pesticides derived from various sources. The most abundant pesticides are acaricides applied by beekeepers to co...

Related Compounds

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