Nitralin

345.37

345.37

225-219-0

697W0VS4HQ

3077

DTXSID9042203

GOLDEN-ORANGE CRYSTALLINE SOLID|FINE CRYSTALLINE, LIGHT YELLOW TO ORANGE|Orange prisms

137

4.66010

Nitralin is a light yellow to orange solid with a mild odor. Sinks in water. (USCG, 1999)

greater than 1 at 68° F (est) (USCG, 1999)

151-152 °C

greater than 437° F at 760 mm Hg (decomposes) (USCG, 1999)

260.5ºC

1.561

Solubility at 25 deg C: methanol 1.1%, isopropanol 0.18%, benzene less than 12.5%

0-6°C

9.3X10-9 mm Hg at 20 deg C; 3.3X10-8 mm Hg at 30 deg C

Oral-Rat LD50: 2000 mg/kg; Oral-Mouse LD50: 2000 mg/kg

Combustion produces toxic nitrogen oxides and nitrogen oxide gases

Decomposes vigorously and exothermically at about 225 deg C /Differential Thermal Analyzer at 5C/min/. The estimated heat of decomposition is 250 cal/g.

MILD CHEMICAL ODOR

No rapid reaction with air. No rapid reaction with water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

NITRALIN decomposes vigorously in a self-sustaining reaction at or above 225°C (USCG, 1999).

435 °F (USCG, 1999)

Noncorrosive

UN30779/PG3

2

50-22

60-61

CY0380000

N,Xn

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

SHELF LIFE OF TECHNICAL PRODUCT IS 3 YR OR MORE WHEN STORED IN FIBER-BOARD DRUMS

P273

H400

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.

DINITROANILINE HERBICIDES. COMPARATIVE SUMMARY; CHEMOSPHERE 9 (1): 67-9 (1980). A COMPARATIVE SUMMARY OF DINITROANILINE HERBICIDES. REVIEW OF DINITROANILINE HERBICIDES IS GIVEN. THE CHEMICAL STRUCTURES ARE INCLUDED. METABOLITES, THE QUALITATIVE COMPOSITION OF RESIDUES, LOCATION IN WHICH VARIOUS METABOLITES MAY BE FOUND FOLLOWING AGRICULTURAL USAGE AND PERSISTENCE ARE DISCUSSED.

Special Hazards of Combustion Products: Irritating oxides of sulfur and nitrogen are formed in fire. Behavior in Fire: Decomposes vigorously in a self-sustaining reaction at or above 225°C (USCG, 1999)

|Warning|H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]|P273, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.

Fire Extinguishing Agents: Water (USCG, 1999)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)

Dust mask; rubber gloves. (USCG, 1999)|Overalls and neoprene or PVC gloves. Conform with normal, safe handling procedures for any pesticide.

Decomposes vigorously and exothermically at about 225 °C /Differential Thermal Analyzer at 5C/min/. The estimated heat of decomposition is 250 cal/g.

CONTACT WITH CONCENTRATED BASES OR TEMP GREATER THAN 200 °C SHOULD BE AVOIDED

As part of the National Pesticide Monitoring Program, 1346 sites in 35 states were sampled for pesticides use(1). The results for nitralin are as follows: Nitralin was used in 7 of these sites, at an average application rate of 0.75 lb/acre, in Alabama, Arkansas, Mississippi, and Tennessee, on cotton and soybean crops(1). In Arkansas, one out of 47 sites contained nitralin at a concentration of 2.47 ppm(1). Concentrations were not given for the other states(1).

moderately toxic

Nitralin's former production and use as a selective pre-emergence herbicide(1) may have resulted in its release to the environment(SRC).

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 980(SRC), determined from a structure estimation method(2), indicates that nitralin will have low mobility in soil(SRC). Volatilization of nitralin is not expected to be important from moist or dry soil surfaces(SRC) given an estimated vapor pressure of 9.3X10-9 mm Hg(3) and an estimated Henry's Law constant of 7X10-9 atm-cu m/mole (calculated from an experimental vapor pressure of 9.3X10-9 mm Hg(3) and an experimental water solubility of 0.6 mg/L at 25 deg(4)). A study on the volatility of dinitroaniline herbicides found that no vapor losses of nitralin were detected at 50 °C from moist Lakeland sand(5) which confirms this prediction(SRC). No losses due to photodecomposition were reported on the surface of a dry Taloka silt loam(6) or on Lakeland sand(7). Nitralin will biodegrade in both aerobic and anaerobic conditions(8) and has half-lives of 2.4 and 3.7 months in Drummer and Cisne soils, respectively(9).|AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 980(SRC), determined from a structure estimation method(2), indicates that nitralin may adsorb to suspended solids and sediment(SRC) in the water. Nitralin is not expected to volatilize from water surfaces based on an estimated Henry's Law constant of 7X10-9 atm-cu m/mole(SRC), calculated using an experimental vapor pressure of 9.3X10-9 mm Hg(3) and an experimental water solubility of 0.6 mg/L at 25 deg(4). An estimated BCF value of 820(4,SRC), from an experimental water solubility of 0.6 mg/l(4), suggests that nitralin will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(5).|ATMOSPHERIC FATE: According to a suggested classification scheme(1), an experimental vapor pressure of 9.3X10-9 mm Hg at 20 °C(2) indicates that nitralin will exist primarily in the particulate phase in the ambient atmosphere. Vapor-phase nitralin is degraded in the atmosphere by reaction with photochemically produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be about 0.64 days(3,SRC). Particulate-phase nitralin may be physically removed from the air by wet and dry deposition(SRC).

CHEMICAL STRUCTURE SIMILARITY OF BENEFIN & NITRALIN & THEIR INSTABILITY TO LIGHT SUGGEST A SIMILAR PATHWAY OF PHOTODECOMPOSITION.|The rate constant for the vapor-phase reaction of nitralin with photochemically produced hydroxyl radicals has been estimated as 2.5X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 0.64 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). When nitralin was applied to the surface of a dry Taloka silt loam (at 1 kg/ha) and exposed to a UV light band of 375-385 nm, 88 and 76 percent remained after 24 hours at 5 and 45 °C, respectively(2). After 24 and 72 hours, no significant losses due to photodecomposition (ultraviolet light at 2900-3400 Ang) were reported for nitralin when comparing radiated and unradiated soil surface treated samples (Lakeland sand) at 26 °C(3). After 7 days of exposing nitralin to unfiltered solar radiation (July) 40.6 percent of the original sample decomposed as a result of photodecomposition(4). After investigating the irradation of nitralin on glass, silica gel, and in acetone or methanol it was found that the reaction proceeded quite rapidly and it was suggested that dimerization occurred at the methylsulfonyl group(5).

An estimated BCF value of 820 was calculated for nitralin(SRC), using an experimental water solubility of 0.6 mg/L(1) and a recommended regression-derived equation(2). According to a classification scheme, this BCF value suggests that bioconcentration in aquatic organisms will be high(3).

831.76 L/kg|IT IS RELATIVELY IMMOBILE IN SOIL & 50% LOSS OCCURS IN ABOUT 30-50 DAYS.|Using a structure estimation method based on molecular connectivity indexes(1), the Koc for nitralin can be estimated to be about 980(SRC). Another value has been experimentally determined to be 960(3). An average value of Koc for nitralin has been determined to be 500 in soil with an organic carbon content of 1-5%(4). According to a recommended classification scheme(2), these Koc values suggest that nitralin has medium to low mobility in soil(SRC).

The Henry's Law constant for nitralin is estimated as 7X10-9 atm-cu m/mole(SRC) from its experimental values for vapor pressure, 9.3X10-9 mm Hg(1), and water solubility, 0.6 mg/L(2). This value indicates that nitralin will be essentially nonvolatile from water surfaces(3,SRC). Nitralin's low vapor pressure(1) and low Henry's Law constant(1,2,SRC) indicate that volatilization from dry and moist soil is not expected to occur(SRC).

NITRALIN IS NOT ABSORBED BY PLANT FOLIAGE & THEREFORE IS NOT A POSTEMERGENCE HERBICIDE. ABSORPTION BY SEED OR ROOTS OF PLANTS IS MEDIATED BY IMBIBITION OF WATER.|Nitralin, as the (14)C-ring-labeled cmpd, has been studied in soybeans, peanuts, peas, and carrots grown under modified field conditions in which the herbicide was soil incorporated at 0.6, 0.75, and 1.0 lb/acre, respectively. In soybeans, the whole plant contained 0.02 ppm equivalents of nitralin. The seeds contained less than 0.01 ppm equivalents of nitralin. Similarly, whole plant parts from peanuts and peas contained an equivalent of 0.03 ppm equivalents of nitralin, with the seeds in a range similar to that of soybeans. Carrots were grown...under greenhouse conditions 11 wk after the initial incorporation study with soybeans. Six wk after planting, carrots were harvested and the roots were divided into peel and cores for analysis. The roots contained 0.006 ppm equivalents of nitralin with 78 and 22% of the radioactivity residing in the peel and cores, respectively.|(14)C-ring-labeled nitralin fed to rats was rapidly excreted, with 52% of the radioactivity being in the urine and 47% in the feces. No (14)CO2 was observed in an expt run in a metabolism cage. Multiple metabolic products were observed. Guernsey cows were fed nitralin at 50 ppm in their ration. Exam of milk revealed no detectable residues of nitralin or its degradation products 4-methylsulfonyl-2,6-dinitro-N-propylaniline, 4-methylsulfonyl-2,6-dinitrophenol and 4-methylsulfonyl-2,6-dinitroaniline. Analyses of various tissues, feces, and urine showed no detectable residues of nitralin or 4-methylsulfonyl-2,-6-dinitrophenol.

PLANAVIN WAS FED TO A CATHETERIZED LACTATING COW AT 5 PPM IN THE FEED RATION FOR 4 DAYS. PLANAVIN OR POSSIBLE SULFUR-CONTAINING METABOLITES WERE NOT DETECTED IN MILK, URINE OR FECES BY ELECTRON AFFINITY & SULFUR-FLAME PHOTOMETRIC GAS CHROMATOGRAPHIC ANALYSIS. THE SULFUR DETECTOR SHOWED THAT THE HERBICIDE RAPIDLY (15 MIN) DECOMPOSED IN FRESH RUMEN FLUID WITH PRODUCTION OF THREE SULFUR-CONTAINING /SRP: METABOLITES NOT DEFINATELY IDENTIFIED/.|Plant metabolites are 2,6-dinitro-4-methylsulfonyl-N-propylaniline, 2,6-dinitro-4-methyl-sulphonylaniline /and/ 2,6-dinitro-4-methylsulfonylphenol.|(14)C-Nitralin was dosed orally to rats 150 mg/kg). The radioactivity was quantitatively (199.8%) between 0-72 hr after dosing. Most of this was distributed equally between the urine and feces; 1.5% was found in the carcass skin and intestines. Structural analysis of the urinary metabolites showed that the metabolism proceeded via a complex multistep series of biotransformations involving nitro-group reduction side-chain oxidation and removal and the subsequent formation of a variety of heterocyclic ring structures. A major metabolite was 7-amino-2-ethyl-5-methylsulfonyl-1-propylbenzimidazole; this accounted for only 3-4% of the ingested radioactivity and was 1 of 5 metabolites produced in this yield. Seven other metabolites were identified none of which was derived from single-step biotransformation of nitralin. The latter simpler metabolites were detected on the incubation of nitralin with rat liver enzymes of the type used in microbial mutagenicity testing. Two pathways nitro-reduction and N-dealkylation) were observed under aerobic conditions but the former greatly predominated under anaerobic conditions.

NITRALIN IS SELECTIVE HERBICIDE ACTING BY DISRUPTION OF PRIMARY CELL WALL FORMATION DURING CELL DIVISION.

Dust irritates eyes. Other forms of exposure produce no observable symptoms. (USCG, 1999)

No cases of clinical toxicity on record. Supportive and symptomatic medical treatment recommended if massive overexposure occurs. EYES: flush with water if irritation occurs. SKIN: wash with soap and water. INGESTION: induce vomiting. (USCG, 1999)

A pruritic scaly erythema developed in a 50-yr-old factory worker who was found to be sensitive to 4-methylsulfonyl-2,6-dinitro-N,N-dipropyianiline (DNA-nitralin); cross-sensitivity to dinitrochlorobenzene was also detected. ...

4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline

WETTABLE POWDER 75%, 89% MILLED CONCENTRATED.|WATER DISPERSABLE LIQUID 425 G AI/L

FORMERLY MANUFACTURED BY SHELL CHEMICAL CO: SHELL INTERNATIONAL CHEMICAL CO.|PLANAVIN IS...REGISTERED FOR USE IN CALIFORNIA ONLY ON POME AND STONE FRUITS, ALMONDS, AND GRAPES.|COMPATIBLE WITH HARD WATER; USE ONLY IN RECOMMENDED COMBINATIONS WITH OTHER PESTICIDES AND FERTILIZERS. CLEANING GLASSWARE AND SPRAY EQUIPMENT: WASH WITH DETERGENT & WATER.|PRE-EMERGENCE WEED CONTROL OF ANNUAL GRASSES & MANY BROAD LEAVED WEEDS IS SUCCESSFUL IN...GROUNDNUTS, RAPE, AND TRANSPLANTED CROPS SUCH AS TOBACCO, TOMATOES, BRASSICAS USING 0.5-0.75 KG AI/HA ON LIGHT SOILS, 1.0-1.5 KG/HA ON HEAVIER SOILS (UP TO 5% OM), NOT USED IN HIGHLY ORGANIC OR PEAT SOILS. SHALLOW MECHANICAL INCORPORATION INTO UPPER 2-4 CM OF SOIL IS RECOMMENDED.|Wheat root growth inhibited at 0.02 mg/kg.

PRODUCT ANALYSIS IS BY INFRARED SPECTROSCOPY OR BY GLC. ANAL METHODS PESTIC PLANT GROWTH REGUL 7: 625 (1973). RESIDUES MAY BE DETERMINED BY GLC...DETAILS OF METHODS ARE AVAILABLE FROM SHELL INTERNATIONAL CHEM CO, LTD.|Product analysis: Extraction (wettable powder) with acetonitrile and determination of IR absorption at 14.07 nm. Elemental analysis: Calculated 12.17% N; 9.37% S. Residue analysis: Extraction of plant material with hexane/isopropanol (soil with diethyl ether, plant oils with acetonitrile), clean-up by column chromatography, and determination by gas chromatography with electron-capture detection.|ANALYSIS OF SOME NO2-CONTAINING HERBICIDES BY GAS CHROMATOGRAPHY WITH ELECTROLYTIC CONDUCTIVITY DETECTION (NITROGEN MODE).

Agrochemicals -> Herbicides|Pharmaceuticals|HERBICIDES