Methoprotryne

271.38

271.38

212-664-0

31X54QGQ17

DTXSID2040286

CRYSTALLINE SOLID|Colorless powder

2933699012

97.3

2.00820

1.186 g/cm³ @ Temp: 20 °C

68-70 °C

444.1ºC at 760 mmHg

222.4ºC

1.543

380 g/l toluene @ 20 deg C

0-6°C

2.85X10-7 mm Hg @ 20 deg C

Oral-Rat LD50: 5000 mg/kg; Oral-Mouse LD50: 2400 mg/kg

Combustion produces toxic sulfur oxide and nitrogen oxide gas

PK: 4.0 @ 21 °C

UN20206.1/PG3

3

22-36/38

26-28-24/25-22

SK8800000

Xn

The warehouse is ventilated, low temperature and dry; stored and transported separately from food materials

STABLE UNDER NORMAL CONDITIONS

P262, P264, P270, P280, P302+P350, P310, P322, P361, P363, P405, P501

H310

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.|Noncombustible containers should be crushed & buried under more than 40 cm of soil. /Herbicides/|Group I Containers: Combustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) should be disposed of in pesticide incinerators or in specified landfill sites. /Organic or metallo-organic pesticides/|Group II Containers: Noncombustible containers from organic or metallo-organic pesticides (except organic mercury, lead, cadmium, or arsenic compounds) must first be triple rinsed. Containers that are in good condition may be returned to the manufacturer or formulator of the pesticide product, or to a drum reconditioner for reuse with the same type of pesticide product, if such reuse is legal under Department of Transportation regulations (eg 49 CFR 173.28). Containers that are not to be reused should be punctured ... and transported to a scrap metal facility for recycling, disposal or burial in a designated landfill. /Organic or metallo-organic pesticides/

|Danger|H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]|P262, P264, P270, P280, P302+P350, P310, P322, P361, P363, P405, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.

The use of personal protective equipment such as glasses, synthetic gloves & /NIOSH approved breathing apparatus/ ... is important. /Herbicides/

Extinguish fire using agent suitable for type of surrounding fire. ... Use water in flooding quantities as fog. Use "alcohol foam" ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Triazine pesticide (compounds and preparations), solid (insecticides, agricultural, not elsewhere classified, other than liquid)/|Avoid breathing dusts & fumes from burning material. Keep upwind. /Triazine pesticide, solid, not otherwise specified, (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/

Avoid contact with eyes, contact with skin, inhalation of dust, & contamination of food & feed.|If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Triazine pesticide, solid, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/ Not elsewhere classified.|Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Triazine pesticide, solid, not otherwise specified (compounds and preparations), (agricultural insecticides, not elsewhere classified, other than liquid)/

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

The major hazards encountered in the use and handling of methoprotryne stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this white, crystalline substance may occur from its manufacture, formulation, and use as a herbicide. Effects from exposure may include nausea, vomiting, and diarrhea. In activities and situations where over exposure may occur, wear a self-contained breathing apparatus and personal protective clothing. If contact should occur, immediately flush affected skin or eyes with running water for at least 15 minutes. Remove contaminated clothing and shoes at the site. While methoprotryne does not ignite easily, it may burn with the production of irritating and poisonous gases. For fires involving this substance, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Methoprotryne may be shipped via air, rail, road, and water, in containers bearing the label "Poison". Small dry spills of methoprotryne may be placed into a clean, dry, covered container for later disposal (liquid solutions are first absorbed in sand or other noncombustible absorbent). Large liquid spills should be diked far ahead to prevent methoprotryne from entering water sources and sewers. Before implementing land disposal of methoprotryne, consult with regulatory agencies for guidance.

moderately toxic

LD50 Rat percutaneous more than 150 mg/kg|LD50 Rat oral > 5000 mg/kg /Technical/

Methoprotryne is a herbicide that is not used in the U.S., but is used in Europe on various crops(1).

TERRESTRIAL FATE: ... TRIAZINES ... ARE NOT READILY DEGRADED BY SOIL MICROORGANISMS. THUS, THEIR RATE OF DECAY IS RELATIVELY SLOW, & AS THESE MATERIALS ALSO DO NOT READILY LEACH FROM THE SOIL, THEY MAY PERSIST FOR QUITE EXTENDED PERIODS OF TIME. /TRIAZINES/|TERRESTRIAL FATE: If methoprotryne is released to soil, it will be expected to exhibit moderate mobility based upon(1) a Koc estimated(5,SRC) using water solubility(4) and, therefore, it may leach to groundwater. It may be susceptible to slow hydrolysis in soil(2,3). Volatilization from near-surface soil is not expected to be an important removal mechanism(SRC). It is unknown whether methoprotryne will biodegrade in soil(SRC).|AQUATIC FATE: If released to water, methoprotryne will not be expected to bioconcentrate in aquatic organisms, adsorb to sediment and suspended particulate matter, or to volatilize. Methoprotryne may be susceptible to slow hydrolysis in water(2) and photooxidation by photochemically produced hydroxyl radicals(1) in water, based upon data for s-triazine herbicides with similar structures to methoprotryne such as prometryn(1,2). It is unknown whether methoprotryne will biodegrade in natural waters(SRC).|ATMOSPHERIC FATE: If methoprotryne is released to the atmosphere, it may be subject to gas-phase reaction with hydroxyl radicals with a half-life of about 2.4 hr estimated for this process(1).|TERRESTRIAL FATE: THE LONG SOIL PERSISTENCE OF THESE CMPD DOES ... CREATE THE PROBLEM OF SOIL CARRY OVER, WHICH CAN DAMAGE SUCCEEDING CASH CROPS. THEREFORE EXTREME CAUTION MUST BE TAKEN IN THEIR APPLICATION ON CROPLAND TO AVOID SUCH INJURY TO FOLLOWING CROPS. /TRIAZINES/

In soil ... cleavage of the thiomethyl group and replacement with hydroxyl /occurs/, presumably after oxidation of the sulfur to sulfoxide and sulfone. Demethylation of the amino groups at C4 and C6, cleavage of the amine moieties and their replacement by hydroxyl, presumably followed by ring opening.|The rate constant for the vapor-phase reaction of prometryn with photochemically produced hydroxyl radicals has been estimated to be 161.9 cu cm/molecule-sec at 25 °C which corresponds to an atmospheric half-life of about 2.4 hr at an atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1). Methoprotryne may be susceptible to slow hydrolysis in water or soil(3), and photooxidation by photochemically produced hydroxyl radicals(4), based upon data for s-triazine herbicides with similar structures with methoprotryne such as prometryn(3,4). The rate of hydrolysis may be increased by various catalysts based upon the observed increase in rate of hydrolysis rates for the chemically similar herbicide atrazine in water solutions upon addition of sterilized soil(5) and humic(6) and fulvic acids(2).

Based upon a water solubility of 320 ppm at 20 °C(1), a BCF of 24 has been estimated(2). Based upon this estimated BCF, methoprotryne will not be expected to bioconcentrate in aquatic organisms(SRC).

ADSORPTION OF TRIAZINES THROUGH EXCHANGE PROCESS TO ORGANIC MATTER & CLAY MINERALS IS DEPENDENT ON PH OF SOLN & ACIDITY OF ADSORBENT SURFACE. HYDROGEN BONDING & HYDROPHOBIC BONDING ARE OTHER MECHANISMS BY WHICH SOIL ORGANIC MATTER ADSORBS TRIAZINE HERBICIDES, ESP AT HIGHER PH LEVELS. ... TRANSPORT FROM SOIL TO WATER OCCURS IN SOLUTION & IN SEDIMENTS. /TRIAZINE HERBICIDES/|Based upon a water solubility of 320 ppm at 20 degC(3), a Koc of 180 has been estimated(4). Based upon this estimated Koc, methoprotryne will be expected to exhibit medium mobility in soil(5). Evidence has been reported which indicates that the basicity of s-triazine herbicides, such as methoprotryne, is not the main factor governing adsorption to soil humic acids(1). It has been shown that the ability of s-triazines herbicides to act as electron donors to electron acceptor quinone-like units of humic acids also plays an important role in the adsorption(2).

Vapor transport losses of triazines are dependent on vapor pressure & pH of evaporating surface, since ionized cmpd are less volatile. /Triazine herbicides/|Based upon a water solubility of 320 mg/l at 20 °C(1) and a vapor pressure of 2.85X10-7 mm Hg at 20 °C(1), the Henry's Law constant for methoprotryne of 3.18X10-10 atm-cu m/mole can be calculated(2,SRC). This value of Henry's Law constant indicates volatilization of methoprotryne will not be environmentally important(2).

After oral administration, 85-95% elimination occurs within 24 hr, in the metabolized form and mainly in the urine. /In plants it is/ absorbed via the leaves and roots.

All of ... /methoxy & methylthio-substituted triazine/ herbicides were rapidly absorbed and metabolized when ingested; amine dealkylation and side chain oxidation are the predominant detoxification reactions. The mercapto derivatives of triazine may also undergo sulfoxidation followed by reaction with hepatic glutathione to yield mercapturic acid derivatives. /Prometon/|In ... plants, cleavage of the thiomethyl group and replacement with hydroxyl /occurs presumably/ after oxidation of the sulfur to sulfoxide and sulfone. Demethylation of the amino groups at C4 and C6, cleavage of the amine moieties and their replacement by hydroxyl, presumably followed by ring opening.

Inhibits photosynthesis.|... Their chief mode of action appears to involve carbohydrate metabolism. The chlorinated s-triazines inhibit starch accumulation by blocking the prodn of sugars. Similar behavior has been shown for the methoxy & methylthio-s-triazines. It has been reported that the s-triazines affect the tricarboxylic acid cycle with activation of phospho-phenyl pyruvate-carboxylase causing the disappearance of sucrose & glyceric acid with the formation of aspartic & malic acids. /s-Triazines/|SINCE CHLOROSIS IS THE FIRST SIGN OF THE EFFECT OF TRIAZINES ON PLANTS, INTERFERENCE WITH CARBON DIOXIDE ASSIMILATION & SUGAR FORMATION CAN BE EXPECTED. STUDIES SHOWING THAT HILL REACTION IS INHIBITED CONFIRMED THIS. /TRIAZINES/

NAUSEA, VOMITING, & DIARRHEA CAN BE EXPECTED TO RESULT FROM INGESTION OF LARGE QUANTITIES. /UREA,- URACIL- & TRIAZINE-BASED HERBICIDES/

GESARAN 2079--WETTABLE POWDER (225 G AI + SIMAZINE (50 G/KG).|Gesaran 25, WP (250 g ai/kg).

The WHO Recommended Classification of Pesticides by Hazard identifies Methoprotryne (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|INTRODUCED IN 1965 BY GEIGY. SWISS PATENT 394,704; BRITISH PATENT 927,348; US PATENT 3,326,914.|Good compatibility with other wettable-powder herbicides.|Discontinued 1984 by Ciba-Geigy Ltd.|CROP ROTATION RESTRICTIONS OR PRECAUTIONS USUALLY ARE NOT REQUIRED BECAUSE OF THE SHORTER RESIDUAL LIFE & ALSO BECAUSE OF THE MUCH GREATER SAFETY MARGIN WHICH MANY SENSITIVE PLANTS HAVE TO METHYLTHIOTRIAZINES COMPARED TO CHLORO OR METHOXYTRIAZINES.

Product analysis by titration with perchloric acid in acetic acid. Bosshardt, HP et al, Assoc Off Anal Chem 54, 749, 1971.|Nine 1,3,5-triazines, one of which was methoprotryne, were separated by thin-layer chromatography. 2-Chloro-1,3,5-triazines were separated from 6-methylthio-1,3,5-triazines with a solvent system of hexane-ethanol on silica gel GF 254 or hexane-ethanol on a mixt of silica gel GF 254 & cellulose MN 300. The 2-chloro- & 6-methylthio-1,3,5-triazines were then individually separated. Visualization was accomplished by 1 of 3 methods, fluorescence inhibition under UV light @ 254 nm, chlorination followed by spraying with benzidine in ethanol, or spraying with silver nitrate in water followed by sodium fluorescein.|RESIDUES MAY BE DETERMINED BY GLC (K RAMSTEINER ET AL, J ASSOC OFF CHEM, 1974, 57, 192). PARTICULARS ARE AVAILABLE FROM CIBA-GEIGY AG.|Product analysis is by gas-liq chromatography (CIPAC Handbook, 1980, 1A, 1302).|For more Analytic Laboratory Methods (Complete) data for METHOPROTRYNE (9 total), please visit the HSDB record page.

Procedure for determining s-triazine herbicides such as methoprotryne in urine & biological tissues by gas chromatography/flame ionization detection is described. Urine samples are extracted with ether & biological tissues with chloroform. Residues obtained after evaporation of solvent are dissolved in dimethylformamide. Most of the lipids can be removed by n-pentane partitioning.

Agrochemicals -> Herbicides|Pharmaceuticals|HERBICIDES