Diphenamid

239.31

239.31

213-482-4

6Z3R6EGA2B

0763

DTXSID8024072

WHITE|CRYSTALS FROM ETHYL ACETATE|WHITE PRISMS|Colorless

29242990

20.3

2.17

White, light Huff Powder

1.17 g/cm³ @ Temp: 23.3 °C

134.5-135.5 °C

382.4ºC

173.3ºC

Solubility in water, g/100ml at 27°C: 0.03

0-6°C

3.00X10-8 mm Hg @ 25 deg C

LD50 orally in rats: 700 mg/kg (Bailey, White)

NO APPRECIABLE ODOR

SOME DECOMP INDICATED AT 210 °C|COMPATIBLE WITH MOST OTHER WETTABLE POWDER HERBICIDAL FORMULATIONS & FERTILIZERS, IF NOT HIGHLY ALKALINE.|Off-white solid /Technical diphenamid/

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

Amides and Imides

DIPHENAMID is an amide. Amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx). This compound is decomposed by strong base or acid.

Non-corrosive

NONH for all modes of transport

3

22-52/53

61

AB8050000

Xn

Separated from strong acids, bases and strong oxidants.

Stable. Incompatible with strong oxidizing agents, strong bases.

P273

H302-H412

Recommendable method: Incineration. Peer-review: Large amt of diphenamid should be burned in incinerator with effluent gas scrubbing when well diluted with other wastes. Solid material can be dissolved in acetone or xylene to ease feeding into incinerator. (Peer-review conclusions of an IRPTC expert consultation (May 1985))|Hydrolysis: Alkali hydrolysis: Slow reaction. Phenylacetic acid and dimethylamine are less phytotoxic.

... Incompatible with highly alkaline materials.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, and P501|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|Aggregated GHS information provided by 130 companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

Nonflammable

Prevent drifting. Keep away from the eyes.

Do NOT let this chemical enter the environment. Then store and dispose of according to local regulations. If appropriate, moisten first to prevent dusting.

Separated from strong acids, bases and strong oxidants.

Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly.

NO open flames.

PREVENT DISPERSION OF DUST!

Use local exhaust.

Wear safety spectacles.

LONG LASTING WEED CONTROL CAN BE EXPECTED FROM RECOMMENDED RATES ... UNDER WARM,MOIST CONDITIONS THE AVG PERSISTENCE @ HERBICIDAL LEVELS IS FROM 3 TO 6 MO. UNDER LOW RAINFALL CONDITIONS, DIPHENAMID MAY BE PERSISTENT IN SOIL.|Theconcn of diphenamid 3-5 days following application of diphenamid at a rate of 4 kg ai/ha in a Russian field was 2.73-2.90 mg/kg(1).

LD50 Rat oral 1050 mg/kg|LD50 Mice oral 600 mg/kg|LD50 Rat percutaneous >225 mg/kg|LD50 Rabbit oral 1500 mg/kg

Diphenamid is not known to occur naturally. (SRC)

Since diphenamid is commercially produced and used as a herbicide(1), it will be released to the environment during production and use(SRC).

TERRESTRIAL FATE: Diphenamid has an estimated Koc of 210(3) and therefore would be expected to leach moderately in soil. Biodegradation is the primary degradative pathway for loss of diphenamid from soils(1-2). The persistence of diphenamid in soil will depend on the soil type, moisture content and the temperature of soil(2). Under warm, moist conditions, the average persistence of diphenamid after application at recommended rates is 3-6 months(2). At higher application rates and under low rainfall or colder temperatures, diphenamid may persist in soil longer than 6 months(5-6). The rate of biodegradation increases moderately in soils that have been previously treated with diphenamid. Diphenamid is non volatile and appears to be stable in sunlight(2).|AQUATIC FATE: Neither hydrolysis(1-2) nor photolysis by sunlight(3-4) should be important for the degradation of diphenamid in water. Based on its ability to undergo biodegradation in soil(5), biodegradation should be the most important process for diphenamid in water(SRC). A Koc value of 210(6) indicates that diphenamid may be moderately adsorbed to suspended solids and sediment in water(SRC). The estimated BCF value of 27(6) indicates that bioconcentration of diphenamid in aquatic organisms will not be important(SRC).|ATMOSPHERIC FATE: Based on a vapor pressure of 3X10-8 mm Hg(1), diphenamid should be present mostly in the particulate form in air, but a small amount may be present in the vapor phase(2,SRC). Based on an estimation method(3), vapor phase diphenamid may be removed from the atmosphere with a half-life of 10.6 hrs due to reaction with photochemically produced hydroxyl radicals(SRC). Partial removal of particulate diphenamid from the air may occur by dry deposition(SRC). Both vapor and particle phase diphenamid may be partly removed from the atmosphere by wet deposition.

/IT/ ... IS NONVOLATILE & APPEARS TO BE RELATIVELY STABLE IN SUNLIGHT.|Diphenamid was photolysed in aqueous solution by ultraviolet irradiation to give mostly N-methyl-2,2-diphenylacetamide.|Diphenamid is stable to hydrolysis in the environmentally significant pH range 5-9(1-2). No degradation occurs over 12 days at 49 °C and a pH of 7(6). When a 10 mg/l aqueous solution of diphenamid was irradiated with an ultraviolet lamp, diphenamid degraded in 15 mins(3). However, no photodecomposition of diphenamid was observed on exposure of aqueous solution of diphenamid to sunlight even after 30 days(4). The inability of sunlight to photodegrade diphenamid in water was also reported by others(5).|Based on an estimation method(1), the rate constant for the reaction of vapor phase diphenamid with hydroxyl radicals in air is 2.42X10-11 cu cm/molecule-sec(SRC). This corresponds to a half-life of 10.6 hrs, based on a 12 hr average OH concentration of 1.5X10+6 radicals/cu cm in the atmosphere.

The bioconcentration factor (BCF) for diphenamid in aquatic organisms has been estimated to be 27(1). The low BCF value indicates that diphenamid would not be expected to bioconcentrate in aquatic organisms(1,SRC).

208.93 L/kg|DIPHENAMID IS NOT TIGHTLY ADSORBED ON SOIL COLLOIDS. IT LEACHES RAPIDLY IN SANDYSOILS BUT SLOWLY IN LOAM OR CLAY SOILS. IN SANDY SOILS, RETENTION OF AN EFFECTIVE CONCN IN THE WEED SEED GERMINATION ZONE WITH HEAVY RAINFALL CAN BE A PROBLEM.|A Koc of 210 for diphenamid has estimated from its water solubility(1-2). According to a suggested classification scheme, this Koc value indicates that diphenamid would be moderately mobile in soil(5). Soil thin layer chromatography studies indicates that the average retention factor (Rf) of diphenamid in a silty loam soil is 0.49(3-4). This Rf value also indicates that diphenamid has moderate mobility in soil(3).

Based on a Henry's Law constant of 2.42X10-11 atm-cu m/mole(1) estimated from the ratio of a vapor pressure of 3.0X10-8 mm Hg(1) and a water solubility of 260 mg/L(1), thevolatilization of diphenamid from water should not be important(2,SRC). Volatilization of diphenamid from soil is also not important(3).|Henry's Law constant = 2.42X10-11 atm-cu m/mole (est)

GROUNDWATER: Diphenamid was not found in 678 ground water samples taken from 676 locations(2). It was detected at a concn 6000 ug/l in a groundwater sample from CA(3). Diphenamid was also detected at a concn 43 ug/l in ground waters under a suspected spill site in a rural area in Ontario,Canada(1).

Exposure to diphenamid is most likely to occur among agricultural workers who formulate and apply the herbicide on fields(SRC). Judging from the spraying of wetable powder, the most probable routes of exposure to diphenamid among this group would be inhalation and dermal contact(1,SRC).|The skin exposure to diphenamid among tree nursery workers at a facility in OR was less than 1%(1). The maximum exposure to diphenamid as indicated by patches attached to clothing was 273 ug/patch(1).

DIPHENAMID ... IS WELL ABSORBED & READILY METABOLIZED IN MAMMALS.|STUDIES WITH POSTEMERGENCE TREATMENTS ON CROPS OR WEEDS INDICATE ONLY A LOW LEVEL OF FOLIAR ABSORPTION. ... /IT/ IS ABSORBED VIA THE ROOTS AND TRANSLOCATED THROUGH THE ROOTS, STEM, & LEAVES.|TOMATO PLANTS (LYCOPERSICON ESCULENTUM MILL, VARIETY SHEYENNE), 27-35 DAYS OLD ... FUMIGATED WITH OZONE PRIOR TO EXPOSING ... ROOTS TO (14)C DIPHENAMID ... DIFFERENCES ... OBSERVED: 1. FUMIGATED PLANTS ABSORBED 70-100% AS MUCH DIPHENAMID AS DID CONTROLS, 2. FUMIGATED PLANTS ... CONTAINED LESS RADIOACTIVITY IN CHCL3-SOL FRACTION ... .|URINARY EXCRETION /BY RATS DOSED WITH (14)C-DIPHENAMID/ OF (14)C WAS FAIRLY RAPID AFTER IP DOSE; 51% WAS PRESENT IN 22 HR URINE & 89% IN 46 HR. THESE RESULTS INDICATED THAT THIS LIPID-SOL UNIONIZED CMPD WAS READILY ABSORBED IN RATS.|For more Absorption, Distribution and Excretion (Complete) data for DIPHENAMID (6 total), please visit the HSDB record page.

The metabolism of diphenamid in cell suspensions of soybeans was studied. When (l4)C-carbonyl-labeled diphenamid was added to the suspensions, the major products were identified as N-hydroxymethyl N-methyl-2,2-diphenylacetamide, N-methyl-2,2-diphenylacetamide, 2,2-diphenylacetamide, an unidentified glucoside, and an acidic conjugate of glucose, malonate and diphenamid.|In cotton, okra, peanut shoots, and soybean shoots, dealkylated products and water-soluble compounds were present. Brightleaf and burley tobacco shoots also had dealkylated products. In cotton, okra, peanut and soybean shoots, the presence of the glucoside and gentiobioside were observed.|Aquatic plants and algae were exposed to diphenamid in trays and jars. The vascular plants and aquatic algae absorbed and removed diphenamid from the water. In algae, water hyacinth, and parrotfeather, N-methyl-2,2-diphenylamide and other unidentified materials were observed.|METABOLISM ... IN CORN ROOTS ... WITH CARBONYL (14)C LABELING. ONLY CMPD IDENTIFIED ... N-METHYL-2,2-DIPHENYLACETAMIDE.|For more Metabolism/Metabolites (Complete) data for DIPHENAMID (14 total), please visit the HSDB record page.

HALF-LIVES FOR (14)C IN BLOOD OF RATS DOSED WITH (14)C-DIPHENAMID ... BY ORAL, IP, & SC ROUTES WERE SIMILAR (ABOUT 4 HR). HOWEVER, BLOOD LEVELS OF (14)C ... GREATER @ PEAK ABOUT 50 MIN AFTER IP DOSING THAN @ PEAK ABOUT 200 MIN AFTER DOSING BY OTHER TWO ROUTES.

Fresh air, rest.

Rinse and then wash skin with water and soap.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

ASSUMED TO ... /HAVE EMETIC/ EFFECTS IN MAN. MAY INDUCE CONVULSIONS.

dimid

The substance can be absorbed into the body by ingestion.

HERBICIDE, OF WHICH APPROXIMATELY 52% IS USED ON FIELD CROPS AND 48% ON VEGETABLE CROPS (1975)

AVAILABLE IN 50 & 80% WETTABLE POWDERS; 4 LB/GAL LIQ DISPERSION, & 5% GRANULES. COMBINATIONS: AVAILABLE AS MIXT OF TREFLAN & DYMID, KNOWN AS TREFMID.|'ENIDE 90W', WP (900 G AI/KG); 'ENIDE 50W', WP (500 G AI/KG);

LAB METHOD OF PURIFICATION: CRUDE PRODUCT CAN BE RECRYSTALLIZED FROM ETHYL ACETATE AND HEXANE OR ETHYL ACETATE ALONE.|... INTRODUCED IN 1960, AS HERBICIDE BY ELI LILLY & CO, UNDER CODE NUMBER "L-34314" & TRADE MARK "DYMID", ALSO "ENIDE" (UPJOHN CO). IT WAS FIRST DESCRIBED AS HERBICIDE BY ALDER, EF ET AL, PROC NC WEED CONTROL CONF, 1960, P 55 & IS PROTECTED BY USP 3,120,434.|TOLERANT CROPS INCL PEANUT, TOMATOES, PEPPERS, IRISH POTATOES, SWEET POTATOES, STRAWBERRIES, APPLE TREES, ORANGE & LIME TREES, SOYBEANS, COTTON, OKRA, TRANSPLANT CABBAGE, DICHONDRA, WOODY ORNAMENTALS ... CEREAL GRAINS ARE SENSITIVE TO ... /IT/ ... SURFACE-APPLIED ... LIGHT RAINFALL OR SPRINKLER IRRIGATION FOLLOWING DIPHENAMID APPLICATION WILL IMPROVE ITS CONTROL OF WEEDS. UNDER CONDITIONS OF DRY WEATHER, FOLLOWING APPLICATION OF DIPHENAMID, SOIL INCORPORATION MAY INCREASE THE EFFICACY OF THE HERBICIDE. DIPHENAMID MAY BE APPLIED IMMEDIATELY AFTER SEEDING THE CROP OR OVER TOP OF TRANSPLANT CROPS ANY TIME AFTER TRANSPLANTING BUT PRIOR TO WEED EMERGENCE. ON PEANUTS DIPHENAMID MAY BE APPLIED AT PLANTING, AT CRACKING, OR UP TO 7 DAYS AFTER CRACKING; WITH THE LATTER TWO APPLICATIONS, DIPHENAMID SHOULD BE COMBINED WITH DINOSEB AMINE. ... RATES: 2.0-6.0 LB/ACRE ... DIPHENAMID WETTABLE POWDER IS NOT SIGNIFICANTLY INFLUENCED IN ITS SPRAYABILITY BY WATER HARDNESS.|Discontinued in 1988 by NOR-AM Chemical Co.

RAPID BIOASSAY FOR DIPHENAMID IN SOIL BASED ON DIFFERENTIAL INHIBITION OF ELONGATION OF OAT ROOTS.|GENERAL SAMPLE, DETERMINATION BY GC.|... RESIDUES MAY BE DETERMINED BY GLC WITH FLAME IONIZATION DETECTION.|Determination of diphenamidresidues in agricultural crops by using GC with a hydrogen flame ionization cell.|The analytical method for residue determinations for diphenamid requires extraction of the crop tissue or soil with a solvent such as acetone, removal of interfering substances on Florisil and alumina columns, and determination by GC utilizing a flame ionization detector. The test sensitivity is approximately 25 ppb.

Agrochemicals -> Herbicides|HERBICIDES