penconazole

Names

[ Name ]:
penconazole

[Synonym ]:
topasmz
(RS)-1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole
EINECS 266-275-6
PENCONAZOL
T5NN DNJ A1Y3&R BG DG
1-[2-(2,4-Dichlorophenyl)pentyl]-1H-1,2,4-triazole
onmex
MFCD00078737
1-[2-(2,4-Dichlorophenyl)-n-pentyl]-1H-1,2,4-triazole
Topas
1-(2,4-Dichloro-β-propylphenethyl)-1H-1,2,4-triazole
topaze
1H-1,2,4-Triazole, 1-[2-(2,4-dichlorophenyl)pentyl]-
topazec
penconazole
topasc
Pine gel
rac-1-[(2R)-2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole

Biological Activity

[Description]:

Penconazole is a typical triazole fungicide, and mainly applied on apples, grapes, and vegetables to control powdery mildew. Penconazole inhibits sterol biosynthesis in fungi. Penconazole decrease AChE activity in the cerebrum and cerebellum of rats[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> AChE

[In Vivo]

Penconazole (67 mg/kg; i.p.; every 2 days during 9 days) induces oxidative stress in rat cerebrum and cerebellum tissues[2]. Penconazole has the ability to induce oxidative damage in the brain of adult rats, as evidenced by an increase of lipid peroxidation and protein oxidation, in addition to the perturbations in the enzymatic and nonenzymatic antioxidant status. Penconazole also affects the cholinergic system, activities of membrane-bound ATPases, and brain histoarchitecture. Penconazole is a potential neurotoxicant pesticide that exerts its neurotoxic effects via the generation of oxidative stress. Penconazole causes a significant inhibition of AChE activity in the cerebrum (11%) and cerebellum (25%) of adult rats[2]. Animal Model: Twelve male Wistar rats[2] Dosage: 67 mg/kg Administration: I.p.; every 2 days during 9 days Result: A significant increase was obtained in the absolute and relative weights of the cerebrum and cerebellum, respectively.

[References]

[1]. Husak VV, et al. Acute exposure to the penconazole-containing fungicide Topas partially augments antioxidant potential in goldfish tissues. Comp Biochem Physiol C Toxicol Pharmacol. 2017;193:1-8.

[2]. Chaâbane M, et al. Penconazole alters redox status, cholinergic function, and membrane-bound ATPases in the cerebrum and cerebellum of adult rats. Hum Exp Toxicol. 2017;36(8):854-866.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
415.3±55.0 °C at 760 mmHg

[ Melting Point ]:
57.6-60.3ºC

[ Molecular Formula ]:
C₁₃H₁₅Cl₂N₃

[ Molecular Weight ]:
284.184

[ Flash Point ]:
204.9±31.5 °C

[ Exact Mass ]:
283.064301

[ PSA ]:
30.71000

[ LogP ]:
3.66

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.602

[ Storage condition ]:
0-6°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ4615000

CHEMICAL NAME :: 1H-1,2,4-Triazole, 1-(2-(2,4-dichlorophenyl)pentyl)-

CAS REGISTRY NUMBER :: 66246-88-6

BEILSTEIN REFERENCE NO. :: 0541488

LAST UPDATED :: 199710

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C13-H15-Cl2-N3

MOLECULAR WEIGHT :: 284.21

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 :: 2125 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: 9,554,1991

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/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: 38,195,1984

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2444 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: 38,195,1984

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H361d-H410

[ Precautionary Statements ]:
P201-P273-P301 + P312 + P330-P308 + P313-P391-P501

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
XZ4615000

[ HS Code ]:
2933990015

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990016

[ Summary ]:
2933990016 1-(2-(2,4-dichlorophenyl)pentyl)-1h-1,2,4-triazole。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 dissipation of three fungicides in a biobed organic substrate and their impact on the structure and activity of the microbial community.

Environ. Sci. Pollut. Res. Int. 20(4) , 2546-55, (2013)

Biopurification systems (BPS) have been introduced to minimise the risk for point source contamination of natural water resources by pesticides. Their depuration efficiency relies mostly on the high b...

Enantiomeric separation of triazole fungicides with 3-μm and 5-μml particle chiral columns by reverse-phase high-performance liquid chromatography.

Chirality 23(6) , 479-86, (2011)

This study used chiral columns packed with 3-μm and 5-μm particles to comparatively separate enantiomers of 9 triazole fungicides, and Lux Cellulose-1 columns with chiral stationary phase of cellulose...

Biological monitoring of pesticide exposures in residents living near agricultural land.

BMC Public Health 11 , 856, (2011)

There is currently a lack of reliable information on the exposures of residents and bystanders to pesticides in the UK. Previous research has shown that the methods currently used for assessing pestic...