759-94-4CCCN(CCC)C(=O)SCCGUVLYNGULCJVDO-UHFFFAOYSA-NEthyl Dipropylthiocarbamate can cause developmental toxicity according to The Environmental Protection Agency (EPA).
759-94-4DTXSID1024091CHEMBL1371350CHEBI:4738Pesticide -> EPA IRIS
Herbicides
Active substance -> EU Pesticides database: Not approved
Pesticides -> Herbicides, Thiocarbamate
Pesticide (EPTC) -> USDA PDB
Pesticide
log Kow = 3.21
3.20
2.77
0.955 (NTP, 1992) - Less dense than water; will float
0.955 @ 30 °C
Relative density (water = 1): 0.95
Colorless liquid
Yellow liquid (technical)
less than 0.1 mg/mL at 72.5 °F (NTP, 1992)
Miscible with common organic solvents, e.g. acetone, ethanol, isopropanol, benzene, xylene, kerosene
Miscible with hydrogen sulfide
In water, 375 mg/l @ 25 °C
Solubility in water, mg/l at 25 °C: 344 (very slightly soluble)
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Warning
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Hazard Traits - Developmental Toxicity
EPTC (Ethyl dipropylthiocarbamate) is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
REACH registered substance: EPTC (EC: 212-073-8)
Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992)
Combustible. Liquid formulations containing organic solvents may be flammable. Gives off irritating or toxic fumes (or gases) in a fire.
Can be absorbed through the skin; May cause CNS effects; [ICSC] May cause skin and mucous membrane irritation; [HSDB] Demonstrates neurotoxic effects in rats and dogs consistent with effects of thiocarbamates; Cardiomyopathy also observed; [Reference #1] A skin and strong eye irritant; May cause skin sensitization; [ECHA REACH Registrations] An irritant and cholinesterase inhibitor; Toxic by ingestion; Harmful by inhalation and skin absorption; [AccuStandard MSDS]
... THE RATE OF (35)S EPTC DEGRADATION IN GERMINATING SEEDS /WAS REPORTED/. DATA ... SHOW A GREATER DEGRADATION ... IN SEEDS OF THOSE SPECIES WHICH ARE RESISTANT TO THIS HERBICIDE THAN IN SUSCEPTIBLE SPECIES. THE RADIOSULFUR ... WAS INCORPORATED INTO CYSTEIC ACID, CYSTINE, METHIONINE, METHIONINE SULFONE & 2 UNIDENTIFIED COMPD.
COMPLETE OXIDATION OF THE ETHYL MOIETY OF THE EPTC MOLECULE TO CO2 BY RATS WAS REPORTED ... . INCREASING THE DOSE OF EPTC ... LED TO A DECR IN (14)CO2 OUTPUT ... . SIX MAJOR LABELED METABOLITES WERE FOUND ... AND THE RELATIVE AMOUNT OF 3 METABOLITES CHANGED WITH DOSE. ONE OF THE MAJOR METABOLITES WAS ... UREA, & 3 OTHERS, WHICH ACCOUNTED FOR 50-70% OF THE TOTAL RADIOACTIVITY IN THE URINE, WERE CONJUGATES OF EPTC OR EPTC-LIKE CMPD.
THIOCARBAMATE HERBICIDES ALSO REACT WITH GLUTATHIONE AFTER OXIDATIVE ACTIVATION. EG, EPTAM & ITS S-OXIDE LOWER HEPATIC GLUTATHIONE WHEN GIVEN TO MICE AND ARE EXCRETED AS A MERCAPTURIC ACID FROM RATS.
THE MAIN SOL METABOLITE WAS CARBAMOYLATED GLUTATHIONE. EPTC-SULFONE REACTED WITH GSH. EPTC WAS PARTIALLY OXIDIZED TO EPTC-SULFOXIDE IN IN VITRO ASSAYS USING 5 DAY OLD SEEDLINGS.
For more Metabolism/Metabolites (Complete) data for EPTAM (9 total), please visit the HSDB record page.
As a general rule, thiocarbamates can be absorbed via the skin, mucous membranes, and the respiratory and gastrointestinal tracts. They are eliminated quite rapidly, mainly via expired air and urine. Two major pathways exist for the metabolism of thiocarbamates in mammals. One is via sulfoxidation and conjugation with glutathione. The conjugation product is then cleaved to a cysteine derivative, which is metabolized to a mercapturic acid compound. The second route is oxidation of the sulfur to a sulfoxide, which is then oxidized to a sulfone, or hydroxylation to compounds that enter the carbon metabolic pool.
ROOT ABSORPTION OF EPTC WAS REPORTED ... IN OAT ... & IN ALFALFA. THE ABSORBED EPTC WAS READILY MOVED UPWARD TO THE FOLIAGE. THIS CHEMICAL IS ALSO ABSORBED BY THE COLEOPTILES & CAN BE TRANSLOCATED DOWNWARD TO THE ROOTS. ... THE RADIOSULFURFROM LABELED EPTC ACCUMULATES IN GROWING STEM & ROOT TIPS AFTER THE APPLICATION TO THE LEAVES. WHEN THE APPLICATION WAS MADE TO THE ROOTS, THE DISTRIBUTION WAS MORE UNIFORM.
... SEEDS OF KIDNEY BEAN, PEA, CORN, & OAT /WERE COVERED/ WITH DRY SOILS CONTAINING VARIOUS LEVELS OF (35)S EPTC, RANGING FROM 10 TO 100 PPM ... . NO SIGNIFICANT AMT OF RADIOACTIVITY WAS FOUND IN THE SEEDS AFTER 6 DAYS ... . A SIGNIFICANT AMT OF RADIOACTIVITY WAS TAKEN UP WHEN THE GERMINATING SEEDS /KIDNEY BEAN, PEA, CORN, & OAT/ WERE COVERED WITH WET SOIL CONTAINING (35)S EPTC. EPTC WAS ALSO TAKEN UP BY SEEDS THAT WERE GERMINATED BETWEEN 2 SHEETS OF FILTER PAPER MOISTENED WITH AN EPTC SOLN.
Wird geladen…
116 °C (OPEN CUP)
116 °C o.c.
261 °F at 20 mmHg (NTP, 1992)
127 °C @ 20 mm Hg
232 °C
Tolerances are established for negligible residues (N) of the herbicide S-ethyl dipropylthiocarbamate in or on the following raw agricultural commodities: almonds, hulls; asparugus; beans, castor; cotton, forage; cottonseed; flaxseed; fruits, citrus; fruits, small; grain crops; grasses, forage; legumes, forage; nuts; pineapples; safflower, seed; strawberries; sunflower, seed; vegetables, fruiting; vegetables, leafy; vegetables, root crop; and vegetables, seed and pod.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. S-Ethyl dipropylthiocarbamate is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0064; Pesticide type: Herbicide; Registration Standard Date: 09/30/83; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): S-Ethyl dipropylthiocarbamate; Data Call-in (DCI) Date(s): 09/04/90, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
Fires involving this compound should be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
Use water spray, foam, powder, carbon dioxide.
Fresh air, rest. Seek medical attention if you feel unwell.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.
Rinse with plenty of water (remove contact lenses if easily possible). Refer for medical attention if irritation persists.
Rinse mouth. Seek medical attention if you feel unwell.
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
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.
EPTC is combustible and could be incinerated. Recommendable method: Incineration. Peer-review: Incineration in a unit with effluent gas scrubbing is recommendable for large amt. (Peer-review conclusions of an IRPTC expert consultation (May 1985))
No acceptable chemical detoxification is available. Empty containers should be triple rinsed. "Triple rinse" means the flushing of containers three times, each time using a volume of the normal diluent equal to approx ten percent of the container's capacity, and adding the rinse liquid to the spray mixture or disposing of it by a method prescribed for disposing of the pesticide.
Personal protection: complete protective clothing, protective gloves, safety goggles and filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Treatment of carbamate poisoning is similar to that of organophosphate poisoning in that atropine sulfate injections readily reverse the effects. For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
ANTAGONISTIC INTERACTION BETWEEN 2,4-D ([2,4-DICHLOROPHENOXY]ACETIC ACID) & EPTC OR OTHER THIOCARBAMATES HAS BEEN REPORTED ... . GENERALLY, THE INHIBITION OF GROWTH IS RELATED TO THE CONCN OF THIOCARBAMATES, & THIS INHIBITION CAN BE REVERSED BY 2,4-D.
THE HERBICIDE SAFENER N-DICHLOROACETYL-1-OXA-4-AZA-SPIRO-4,5-DECANE IS OF SIMILAR EFFICIENCY AS THE EXTENSIVELY USED N,N-DIALLYL-2,2-DICHLOROACETAMIDE & STRUCTURALLY RELATED 3-(DICHLOROACETYL)-2,2-DIMETHYL-1,3-OXAZOLIDINE IN REDUCING EPTC INJURY TO MAIZE.
Data concerning the effects of thiocarbamates on man are scarce. However, cases of irritation and sensitization have been observed among agricultural workers. Some thiocarbamates, e.g., molinate, have an effect on sperm morphology and, consequently, on reproduction. However, no teratogenic effects have been observed. EPTC was not mutagenic when tested in a series of assays with microbial and human cell culture lines. The results of mutagenicity studies have shown that thiocarbamates containing dichloroallyl groups are highly mutagenic. Some thiocarbamates are acetylcholine esterase inhibitors. Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.
LC50 ASELLUS 23 MG/L/96 HR @ 15 °C (95% CONFIDENCE LIMIT 15-36 MG/L), MATURE TECHNICAL MATERIAL, 98%; STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
LC50 GAMMARUS FASCIATUS 66 MG/L/96 HR @ 15 °C, MATURE, TECHNICAL MATERIAL, 98%; STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
LC50 SALMO CLARKI (CUTTHROAT TROUT) 17 MG/L/96 HR @ 10 °C (95% CONFIDENCE LIMIT 15-19 MG/L), WT 1.0 G, TECHNICAL MATERIAL, 98%; STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
LC50 SALVELINUS NAMAYCUSH (LAKE TROUT) 16.2 MG/L/96 HR @ 10 °C (95% CONFIDENCE LIMIT 14.8-17.7 MG/L), WT 0.9 G, TECHNICAL MATERIAL, 98%; STATIC BIOASSAY WITHOUT AERATION, PH 7.2-7.5, WATER HARDNESS 40-50 MG/L AS CALCIUM CARBONATE AND ALKALINITY OF 30-35 MG/L.
For more Ecotoxicity Values (Complete) data for EPTAM (6 total), please visit the HSDB record page.
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 136-280(2-4) indicate that eptam is expected to have moderate mobility in soil(SRC). The leaching of eptam in soil decreases as clay and organic matter increases(2). Volatilization of eptam from moist soil surfaces is expected to be an important fate process(SRC), given an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-2 mm Hg(12), and water solubility, 375 mg/l(5). Eptam has a half-life in wet soil of 3.4 hrs if eptam is applied when the surface is wet at the time of application and is not immediately incorporated into the soil(6). Microbial breakdown is reported as a main removal process of eptam from soil(2). In a loam soil at 25 °C inoculated with eptam degraders, approximately 100% eptam was removed from the soil within 15 days; 45% of the loss was due to biodegradation; 55% removal by volatilization was reported in the sterile sample(7). The biodegradation half-life of eptam (initial concn of 5 ppm) at 25 °C in Regina heavy clay soil (pH 7.5) and Weyburn loam (pH 7.0) was 4-5 wks and 4 wks, respectively(8). The half-life in moist loam soil at 21-27 °C is about 1 week(2). Eptam was reported to persist in soil for 4 wks(9). According to the US Dept of Agriculture's Pesticide Properties Database, the soil half-life of eptam is 6 days(10). Soil biodegradation studies suggest that eptam is somewhat more persistent under anaerobic conditions with half-lives of 31 to 127 days(4). Eptam was applied to soil at a depth of 10 cm; 13% of the initial mass of eptam volatilized in 10 days(11).
AQUATIC FATE: Based on a classification scheme(1), Koc values of 136 to 280(2-4) indicate that eptam is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(5), based upon an estimated Henry's Law constant of 1.6X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 2.4X10-2 mm Hg(8), and water solubility, 375 mg/l(6). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 and 28 days, respectively(SRC). Eptam does not undergo hydrolysis under environmentally relevant conditions (pH 5 to 9)(4). Biodegradation of eptam is expected to occur in aqueous systems based on its biodegradation in soil(4). According to a classification scheme(7), a range of experimental BCFs of 37 to 110(4), suggest the potential for bioconcentration in aquatic organisms is moderate to high(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), eptam, which has a vapor pressure of 2.4X10-2 mm Hg at 25 °C(2), is expected to exist solely in the vapor-phase in the ambient atmosphere(SRC). Vapor-phase eptam 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 14 hrs(SRC), calculated from its rate constant of 3.18X10-11 cu cm/molecule-sec at 25 °C(3). Physical removal from air by wet deposition (dissolution in clouds, rainfall, etc) occurs(SRC); eptam has been detected in widespread rainwater monitoring studies(4,5). Degradation rates associated with rainwater and clouds are unknown(SRC); these monitoring studies suggest that widespread atmospheric dispersal is possible(4).
The substance can be absorbed into the body by inhalation, through the skin and by ingestion.
Inhalation (L793) ; oral (L793); dermal (L793)
Some thiocarbamates (EPTC, Molinate, Pebulate, and Cycloate) share a common mechanism of toxicity, i.e. the inhibition of acetylcholinesterase. An acetylcholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.
See Inhalation.
As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)
During its use as a herbicide, eptam is released(1) via ground sprayers, cultivation equipment, soil injection and irrigation(2). Eptam may undergo surface runoff via rainfall(3). Herbicidal application of eptam can result in contamination of surrounding areas through accidental spills and spray drift(4,5).
Tolerances are established for negligible residues (N) of the herbicide S-ethyl dipropylthiocarbamate in or on the following raw agricultural commodities: almonds, hulls; asparugus; beans, castor; cotton, forage; cottonseed; flaxseed; fruits, citrus; fruits, small; grain crops; grasses, forage; legumes, forage; nuts; pineapples; safflower, seed; strawberries; sunflower, seed; vegetables, fruiting; vegetables, leafy; vegetables, root crop; and vegetables, seed and pod.
As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. S-Ethyl dipropylthiocarbamate is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA, as amended in 1988. Case No: 0064; Pesticide type: Herbicide; Registration Standard Date: 09/30/83; Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the Reregistration Eligibility Decision (RED) document.; Active ingredient (AI): S-Ethyl dipropylthiocarbamate; Data Call-in (DCI) Date(s): 09/04/90, 10/13/95; AI Status: The producers of the pesticide has made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner.
(AZ) ARIZONA 180 ug/l
(FL) FLORIDA 180 ug/L
(MN) MINNESOTA 200 ug/l
(WI) WISCONSIN 250 ug/l
... VAPORS MAY BE ABSORBED BY FOLIAGE.
... AFTER A 0.6 MG DOSE /EPTC, ORAL, TO RATS/ 8% WAS EXCRETED IN THE URINE, 4% IN THE FECES, & 85% IN THE EXPIRED AIR, WHEREAS AFTER A DOSE OF 100.6 MG, 36, 11, & 38% WERE EXCRETED BY THESE ROUTES RESPECTIVELY. THE LARGER DOSE WAS ALSO EXCRETED MORE SLOWLY.
INCR THE DOSE OF EPTC /IN RATS/ FROM 0.63 TO 103 MG PER RAT LED TO A ... CORRESPONDING INCR IN URINARY EXCRETION OF RADIOACTIVITY. ... THE TIME FOR COMPLETE URINARY ELIMINATION OF RADIOACTIVITY WAS LIKEWISE EXTENDED /TO APPROX 35 HR FOR HIGHER DOSE/.
Used as selective herbicide for control of many types of weeds in food crops, non-food use sites, and residential and public sites; [HSDB]
Farming (Pesticides) [Category: Industry]
For EPTAM (USEPA/OPP Pesticide Code: 041401) ACTIVE products with label matches. /SRP: Registered for use in the U.S. but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
SELECTIVE HERBICIDE FOR CONTROL OF A VARIETY OF WEEDS
Eptam is used in every region of the United States in the agricultural production of a wide variety of food crops. Eptam is used on non-food use sites such as citrus nursery stock, non-bearing fruit orchards, evergreens, deciduous trees, scrubs, pine seeding nurseries, and ornamentals. Eptam is also used at residential/public sites such as parks, flower gardens, turf grasses, and golf course sand traps.
Control of annual and perennial grasses and some broad-leaved weeds in crops.
HERBICIDE, OF WHICH APPROXIMATELY 59% IS USED ON CORN, 31% ON VEGETABLES, 10% ON SUGAR BEETS (1975)
(1975) 2.91X10+9 GRAMS (CONSUMPTION)
Based on available pesticide survey usage information for the years of 1987 through 1996, an annual estimate of EPTC total domestic usage averaged approximately 20 million pounds for almost 6 million acres treated. Most of the usage is in CA, MI, OR, PA, ND, MN, AZ, SC, NC, AR, MT, IL, NE, LA, TX, KY, TN, AND CO.
REACTION OF ETHYL MERCAPTAN WITH PHOSGENE TO PRODUCE ETHYL CHLOROTHIOFORMATE, FOLLOWED BY REACTION OF THIS WITH DI-N-PROPYLAMINE
IT MAY BE SYNTHESIZED EITHER BY THE REACTION OF ETHANETHIOL & DIPROPYLCARBAMOYL CHLORIDE, FORMED FROM DIPROPYLAMINE & PHOSGENE; OR BY THE REACTION OF DIPROPYLAMINE WITH ETHYL CHLOROTHIOFORMATE.
USEPA/OPP Pesticide Code 041401; Trade Names: EPTAM; Eradicane.
Emulsifiable concentrate, granules
Carbamothioic acid, N,N-dipropyl-, S-ethyl ester: ACTIVE
EPTC is sometimes supplied in a mixture with N,N-diallyl-2,2-dichloroacetamide, which is supposed to be less toxic to maize.
Applied pre-planting with soil incorporation. Combinations with the safener dichlormid are used for herbicidal control in maize.
VerwendenA preemergence herbicide.