Metribuzin

Names

[ Name ]:
Metribuzin

[Synonym ]:
4-amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one
Lexone DF
Sencorer
Sencoral
Sencorex
1,2,4-triazinone
MFCD00055525
Sengoral
4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one
4-amino-6-tert-butyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one
4-amino-6-tert-butyl-3-methylsulfanyl-1,2,4-triazin-5-one
Sencor 75DF
4-Amino-6-(2-methyl-2-propanyl)-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-one
BAY 6159H
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one
Sencor DF
Sencor 4
4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5-one
EINECS 244-209-7
Sencor
Lexone
Metribuzine
1,2,4-Triazin-5(4H)-one, 4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-
4-Amino-6-tert-butyl-3-(methylsulfanyl)-1,2,4-triazin-5(4H)-on
Metribuzin
Senkor
Zenkor
Sencorex L.F.

Biological Activity

[Description]:

Metribuzin is a low-cost non-selective herbicide that belongs to the chemical class of triazinones. Metribuzin hinders DNA synthesis in treated plants and acts on photosystem II, ultimately inhibiting photosynthesis. Metribuzin provides good control of important annual grass and broad-leaf weeds[1].

[Related Catalog]:

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Research Areas >> Others

[References]

[1]. Whitney Pilcher, et al. Genome-wide Microarray Analysis Leads to Identification of Genes in Response to Herbicide, Metribuzin in Wheat Leaves. PLoS One. 2017 Dec 11;12(12):e0189639.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
312.4±25.0 °C at 760 mmHg

[ Melting Point ]:
125°C

[ Molecular Formula ]:
C₈H₁₄N₄OS

[ Molecular Weight ]:
214.288

[ Flash Point ]:
142.7±23.2 °C

[ Exact Mass ]:
214.088837

[ PSA ]:
99.10000

[ LogP ]:
1.30

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.618

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XZ2990000

CHEMICAL NAME :: as-Triazin-5(4H)-one, 4-amino-6-tert-butyl-3-(methylthio)-

CAS REGISTRY NUMBER :: 21087-64-9

BEILSTEIN REFERENCE NO. :: 0746650

LAST UPDATED :: 199712

DATA ITEMS CITED :: 34

MOLECULAR FORMULA :: C8-H14-N4-O-S

MOLECULAR WEIGHT :: 214.32

WISWESSER LINE NOTATION :: T6NN DNVJ CS1 DZ FX1&1&1

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 :: 1100 mg/kg

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: -,C204,1991

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

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >860 mg/m3/4H

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: 12,127,1987

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

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

REFERENCE :: 85JCAE "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986 Volume(issue)/page/year: -,1001,1986

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 239 mg/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: 12,127,1987

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 814 mg/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: 12,127,1987

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 564 mg/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: 12,127,1987

TYPE OF TEST :: LC - Lethal concentration

ROUTE OF EXPOSURE :: Inhalation

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >860 mg/m3/4H

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

REFERENCE :: 85INA8 "Documentation of the Threshold Limit Values and Biological Exposure Indices," 5th ed., Cincinnati, OH, American Conference of Governmental Industrial Hygienists, Inc., 1986 Volume(issue)/page/year: 6,1042,1991

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1 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: 12,127,1987

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 210 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: PCBPBS Pesticide Biochemistry and Physiology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1971- Volume(issue)/page/year: 23,123,1984

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 367 mg/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: 12,127,1987

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: >500 mg/kg

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

REFERENCE :: 85JFAN "Agrochemicals Handbook," with updates, Hartley, D., and H. Kidd, eds., Nottingham, Royal Soc. of Chemistry, 1983-86 Volume(issue)/page/year: A280,1983

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >20 gm/kg

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: -,C204,1991

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 250 mg/kg

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

REFERENCE :: 85DPAN "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976 Volume(issue)/page/year: -,-,1971/1976

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 164 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: 8,573,1987

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

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: 168 mg/kg

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: -,C204,1991 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 64800 ug/kg/15W-C

TOXIC EFFECTS :: Brain and Coverings - other degenerative changes

REFERENCE :: JTEHD6 Journal of Toxicology and Environmental Health. (Hemisphere Pub., 1025 Vermont Ave., NW, Washington, DC 20005) V.1- 1975/76- Volume(issue)/page/year: 30,209,1990

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4550 mg/kg/26W-I

TOXIC EFFECTS :: Immunological Including Allergic - increased immune response

REFERENCE :: GISAAA Gigiena i Sanitariya. For English translation, see HYSAAV. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1- 1936- Volume(issue)/page/year: 52(11),76,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 13140 mg/kg/2Y-C

TOXIC EFFECTS :: 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: 12,127,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 27375 mg/kg/2Y-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

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: 12,127,1987 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 gm/kg

SEX/DURATION :: female 6-15 day(s) after conception

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: 12,127,1987 *** REVIEWS *** ACGIH TLV-Not classifiable as a human carcinogen DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 ACGIH TLV-TWA 5 mg/m3 DTLVS* The Threshold Limit Values (TLVs) and Biological Exposure Indices (BEIs) booklet issues by American Conference of Governmental Industrial Hygienists (ACGIH), Cincinnati, OH, 1996 Volume(issue)/page/year: TLV/BEI,1997 *** U.S. STANDARDS AND REGULATIONS *** EPA FIFRA 1988 PESTICIDE SUBJECT TO REGISTRATION OR RE-REGISTRATION FEREAC Federal Register. (U.S. Government Printing Office, Supt. of Documents, Washington, DC 20402) V.1- 1936- Volume(issue)/page/year: 54,7740,1989 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-AUSTRALIA:TWA 5 mg/m3 JAN 1993 OEL-BELGIUM:TWA 5 mg/m3 JAN 1993 OEL-DENMARK:TWA 5 mg/m3 JAN 1993 OEL-FRANCE:TWA 5 mg/m3 JAN 1993 OEL-THE NETHERLANDS:TWA 5 mg/m3 JAN 1993 OEL IN BULGARIA, COLOMBIA, JORDAN, KOREA check ACGIH TLV OEL IN NEW ZEALAND, SINGAPORE, VIETNAM check ACGIH TLV *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH RECOMMENDED EXPOSURE LEVEL (REL) : NIOSH REL TO METRIBUZIN-air:10H TWA 5 mg/m3 REFERENCE : NIOSH* National Institute for Occupational Safety and Health, U.S. Dept. of Health, Education, and Welfare, Reports and Memoranda. Volume(issue)/page/year: DHHS #92-100,1992

Safety Information

[ Symbol ]:

GHS02, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H225-H302-H302 + H312 + H332-H312-H319-H332

[ Precautionary Statements ]:
P210-P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R50/53

[ Safety Phrases ]:
2-60-61-36-26-16

[ RIDADR ]:
UN3077 9/PG 3

[ RTECS ]:
XZ2990000

[ HS Code ]:
2933699014

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933699014

[ Summary ]:
2933699014 4-amino-6-(tert-butyl)-3-(methylthio)-1,2,4-triazin-5(4h)-one。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

Quantification of triazine herbicides in soil by microwave-assisted extraction and high-performance liquid chromatography.

Environ. Monit. Assess. 178(1-4) , 111-9, (2011)

A method for the determination of herbicides residues, triazine (atrazine, metribuzin, ametryn, and terbutryn), in soil samples with high-performance liquid chromatography (HPLC)-UV detection is descr...

Controlled release formulations of metribuzin: release kinetics in water and soil.

J. Environ. Sci. Health B 45 , 330-335, (2010)

Controlled release (CR) formulations of metribuzin in Polyvinyl chloride [(PVC) (emulsion)], carboxy methyl cellulose (CMC), and carboxy methyl cellulose-kaolinite composite (CMC-KAO), are reported. K...

Reduced downward mobility of metribuzin in fly ash-amended soils.

J. Environ. Sci. Health B 48(7) , 587-92, (2013)

Metribuzin, a triazine herbicide, is poorly sorbed in the soils, therefore leaches to lower soil profile. Fly ash amendment, which enhanced metribuzin sorption in soils, may play a significant role in...