Pyributicarb

Names

[ Name ]:
Pyributicarb

[Synonym ]:
Carbamothioic acid, N-(6-methoxy-2-pyridinyl)-N-methyl-, O-[3-(1,1-dimethylethyl)phenyl] ester
O-(3-tert-Butylphenyl) (6-methoxypyridin-2-yl)methylcarbamothioate
(6-Méthoxy-2-pyridinyl)méthylthiocarbamate de O-[3-(2-méthyl-2-propanyl)phényle]
O-(3-tert-Butylphenyl)-(6-methoxypyridin-2-yl)methylthiocarbamat
TSH-888
O-[3-(1,1-Dimethylethyl)phenyl] (6-methoxy-2-pyridinyl)methylcarbamothioate
Pyributicarb [ISO]
O-[3-(1,1-dimethylethyl)phenyl] N-(6-methoxy-2-pyridinyl)-N-methylcarbamothioate
Carbamothioic acid,(6-methoxy-2-pyridinyl)methyl-,O-(3-(1,1-dimethylethyl)phenyl) ester
O-(3-tert-butylphenyl) N-(6-methoxypyridin-2-yl)-N-methylcarbamothioate
O-[3-(2-Methyl-2-propanyl)phenyl]-(6-methoxy-2-pyridinyl)methylthiocarbamat
O-[3-(2-Methyl-2-propanyl)phenyl] (6-methoxy-2-pyridinyl)methylcarbamothioate
O-3-tert-Butylphenyl 6-methoxy-2-pyridyl(methyl)thiocarbamate
Thiocarbamic acid,N-(6-methoxy-2-pyridyl)-N-methyl-,O-3-tert-butylphenyl ester

Biological Activity

[Description]:

Pyributicarb, a carbamate-type herbicide, is a potent activator of both CYP3A4 gene and human pregnane X receptor (hPXR).

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Cytochrome P450

Research Areas >> Inflammation/Immunology

[Target]

CYP3A4[1], hPXR[2]

[In Vitro]

Pyributicarb, a carbamate-type herbicide, is a potent activator of both CYP3A4 gene and human pregnane X receptor (hPXR). Pyributicarb is found to increase the CYP3A4 reporter activity at 0.1 to 1 μM more strongly than typical CYP3A4 inducer rifampicin. Expression of hPXR-siRNA clearly diminishes the Pyributicarb-stimulated CYP3A4 reporter activity in 3-1-10 cells and decreases the endogenous CYP3A4 mRNA levels in HepG2 cells[1]. Pyributicarb induces luciferase transcription via hPXR at low concentrations in the order of 10 nM. The relative potency of Pyributicarb for hPXR is 8.6-fold that of rifampicin (RIF)[2].

[In Vivo]

Pyributicarb causes enhancement of CYP3A4-derived reporter activity in mouse livers introduced with hPXR by adenovirus[1].

[Cell Assay]

HepG2-derived cells stably expressing the CYP3A4 reporter gene (3-1-10 cells) are used in this experiment. The cells are treated with 0.3 to 30 μM Pyributicarb for 48 h. Then reporter activities are determined[1].

[Animal admin]

Male ICR mice (5 weeks old) are used and fed standard rodent chow. After 18-h fasting, mice are injected i.v. with adenovirus [4.0 ×109 50% titer culture infectious dose (TCID50)/mouse]. Three days after the infection, vehicle (0.5% methyl cellulose/saline) or Pyributicarb (100 mg/kg/day) is administered p.o. for 2 consecutive days. Animals are killed 20 h after the last dose[1].

[References]

[1]. Matsubara T, et al. Assessment of human pregnane X receptor involvement in pesticide-mediated activation of CYP3A4 gene. Drug Metab Dispos. 2007 May;35(5):728-33.

[2]. Kojima H, et al. Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. Toxicology. 2011 Feb 27;280(3):77-87.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
427.8±55.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₈H₂₂N₂O₂S

[ Molecular Weight ]:
330.444

[ Flash Point ]:
212.5±31.5 °C

[ Exact Mass ]:
330.140198

[ PSA ]:
75.47000

[ LogP ]:
5.21

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

[ Index of Refraction ]:
1.599

[ Storage condition ]:
0-6°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XK4962000

CHEMICAL NAME :: Thiocarbamic acid, N-(6-methoxy-2-pyridyl)-N-methyl-, O-3-tert-butylphenyl ester

CAS REGISTRY NUMBER :: 88678-67-5

LAST UPDATED :: 199706

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C18-H22-N2-O2-S

MOLECULAR WEIGHT :: 330.48

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 :: >5 gm/kg

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

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (57),30,1990

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

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >6520 mg/m3/4H

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

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (57),30,1990

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (57),30,1990

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (57),30,1990

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: JPIFAN Japan Pesticide Information. (Japan Plant Protection Assoc., 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) No.1-61, 1969-92. For publisher information, see AGJAEP. Volume(issue)/page/year: (57),30,1990

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 30030 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Endocrine - hypoglycemia Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 219 gm/kg/2Y-C

TOXIC EFFECTS :: Liver - other changes Kidney, Ureter, Bladder - urine volume decreased Blood - normocytic anemia

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 328 gm/kg/78W-C

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 1368 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - other changes Blood - changes in erythrocyte (RBC) count

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 24813 mg/kg/1Y-C

TOXIC EFFECTS :: Liver - other changes Liver - changes in liver weight Endocrine - changes in thyroid weight

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 845 mg/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - abortion

REFERENCE :: NNGADV Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. (Nippon Noyaku Gakkai, 1-43-11, Komagome, Toshima-ku, Tokyo 170, Japan) V.1- 1976- Volume(issue)/page/year: 15,503,1990

Safety Information

[ Symbol ]:

GHS09

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H410

[ Precautionary Statements ]:
P273-P501

[ Hazard Codes ]:
N

[ Risk Phrases ]:
50/53

[ Safety Phrases ]:
61

[ RIDADR ]:
UN 3077 9 / PGIII

[ RTECS ]:
XK4962000

[ HS Code ]:
2933399029

Customs

[ HS Code ]: 2933399029

[ Summary ]:
2933399029 o-(3-(tert-butyl)phenyl) (6-methoxypyridin-2-yl)(methyl)carbamothioate。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%