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DINITROANILINE HERBICIDES

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Classification   |    Detailed evidence-based information

Substances Included Synonyms

Therapeutic Toxic Class

    A) These agents are selective pre-emergence substituted dinitroaniline herbicides used on a wide variety of crops for the control of annual grasses and broadleaf weeds. The herbicides are often applied aerially. They are only slightly soluble in water, have low vapor pressures and are moderately persistent herbicides in the soil. They are degraded in the environment to non-toxic products. Dinitroaniline herbicides are of very low order toxicity to mammals.

Specific Substances

    A) BENFLURALIN
    1) a,a,a-Trifluoro-2,6-dinitro-N,N-ethylbutyl-p-toluidine
    2) Balan
    3) Balfin
    4) Banafine
    5) Benalan
    6) Benefex
    7) Benefin
    8) Bethrodine
    9) Binnell
    10) Blulan
    11) Bonalan
    12) Carpidor
    13) EL-110
    14) Emblem
    15) L 54521
    16) N-Butyl-2,6-dinitro-N-ethyl-4-trifluoromethylaniline
    17) Quilan
    18) Molecular Formula: C13-H16-F3-N3-O4
    19) CAS 1861-40-1
    BUTRALIN
    1) Aniline, N-sec-butyl-4-tert-butyl-2,6-dinitro-
    2) 70-314B
    3) 72-A34
    4) A 820
    5) Amchem 70-25
    6) Amchem A-280
    7) AMEX
    8) AMEX 820
    9) Butalin
    10) Butraline
    11) Dibutalin
    12) N-sec-Butyl-4-tert-butyl-2,6-dinitroaniline
    13) Rutralin
    14) Tamex
    15) Molecular Formula: C14-H21-N3-O4
    16) CAS 33629-47-9
    DINITRAMINE
    1) 3-Diethylamino-2,4-dinitro-6-trifluoromethylaniline
    2) Cobex
    3) Cobexo
    4) Dinintroamine
    5) USB-3584
    6) Molecular Formula: C11-H13-F3-N4-O4
    7) CAS 29091-05-2
    ETHALFLURALIN
    1) Buvalin
    2) EL-161
    3) Sonalan
    4) Molecular Formula: C13-H14-F3-N3-O4
    5) CAS 55283-68-6
    FLUCHLORALIN
    1) BAS 392-H
    2) BAS 3920
    3) BAS 3921
    4) BAS 3921H
    5) BAS 3922
    6) BAS 3924H
    7) Basalin
    8) Molecular Formula: C12-H13-Cl-F3-N3-O4
    9) CAS 33245-39-5
    ISOPROPALIN
    1) Aniline, 2,6-dinitro-N,N-dipropyl-p-isopropyl-
    2) 2,6-Dinitro-N,N-dipropyl-4-isopropylaniline
    3) 2,6-Dinitro-N,N-dipropylcumidine
    4) 4-Isopropyl-2,6-dinitro-N,N-dipropylaniline
    5) Cumidine, 2,6-dinitro-N,N-dipropyl-
    6) EL-179
    7) Isopropaline
    8) Paarlan
    9) Molecular Formula: C15-H23-N3-O4
    10) CAS 33820-53-0
    11) CAS 34113-21-8
    METHALPROPALIN
    1) METHALPROPALIN
    NITRALIN
    1) 2,6-Dinitro-N,N-dipropyl-4-(methylsulfonyl)benzenamine
    2) Nitraline
    3) Planavin
    4) Planavin 75
    5) Planuin
    6) SD 11831
    7) Molecular Formula: C13-H19-N3-O6-S
    8) CAS 4726-14-1
    ORYZALIN
    1) 4-(Dipropylamino)-3,5-Dinitrobenzene Sulfonamide
    2) 3,5-Dinitro-N,N, Dipropylsulfanilamide
    3) Dirimal
    4) EL 119
    5) Rycelan
    6) Rycelon
    7) Ryzelan
    8) Surflan
    9) Sulfanilamide, 3,5-Dinitro-N(SUP 4),N(SUP4)-
    10) Dipropyl-
    11) NIOSH/RTECS WO 9350000
    12) Molecular Formula: C12-H18-N4-O6-S
    13) CAS 19044-88-3
    PENDIMETHALIN
    1) 3,4-Xylidine,2,6-dinitro-N-(1-ethylpropyl)-
    2) AC 92553
    3) Accotab
    4) Herbadox
    5) Horbadox
    6) N-(3-Pentyl)-3,4-dimethyl-2,6-dinitroaniline
    7) Pendimethaline
    8) Penoxalin
    9) Penoxaline
    10) Penoxyn
    11) Phenoxalin
    12) Prowl
    13) Stomp
    14) Stomp 330D
    15) Stomp 330E
    16) Tendimethalin
    17) Wayup
    18) Molecular Formula: C13-H19-N3-O4
    19) CAS 40487-42-1
    20) CAS 64667-17-0
    PRODIAMINE
    1) 5-Dipropylamino-a,a,a-trifluoro-4.6-dinitro-o-toluidine
    2) Blockade
    3) CN-11-2936
    4) Endurance
    5) Kusablock
    6) Marathon
    7) USB-3153
    8) Molecular Formula: C13-H17-F3-N4-O4
    9) CAS 29091-21-2
    PROFLURALIN
    1) CGA 10832
    2) ER5461
    3) GA-10832
    4) Pregard
    5) Profluraline
    6) Tolban
    7) Molecular Formula: C14-H16-F3-N3-O4
    8) CAS 11096-25-6
    9) CAS 26399-36-0
    TRIFLURALIN
    1) Trifluraline
    2) Trifluoralin
    3) a,a,a-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
    4) 2,6-dinitro-N,N-dipropyl-4-trifluoromethylaniline
    5) 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzeneamine
    6) Trifluoralin
    7) Molecular Formula: C13-H16-F3-N3-O4
    8) CAS 1582-09-8

Available Forms Sources

    A) FORMS
    1) BENFLURALIN is a yellow-orange crystalline solid with no appreciable odor (HSDB , 2002).
    2) DINITRAMINE is non-corrosive yellow crystals (HSDB , 2002).
    3) FLUCHLORALIN is an orange-yellow crystalline solid with faint medicinal odor (HSDB , 2002).
    4) ISOPROPALIN is a non-corrosive red-orange liquid (HSDB , 2002).
    5) NITRALIN is a golden-orange crystalline solid or a fine crystalline, light yellow to orange solid with a mild chemical odor (HSDB , 2002).
    6) ORYZALIN is a yellow-orange crystalline solid with no appreciable odor, or a bright orange opaque liquid with a slight aromatic odor (HSDB , 2002). It is manufactured by Elanco and distributed under the trade names of Dirimal, Surflan, and EL-119.
    7) PENDIMETHALIN is orange-yellow crystals with a fruit-like odor (HSDB , 2002). It is available in emulsifiable concentrate, wettable powder, or dispersible granule formulations ((Anon, 1996)).
    8) PROFLURALIN is yellow-orange crystals or liquid with no appreciable odor (HSDB , 2002).
    9) TRIFLURALIN is yellow-orange crystals which is stable to hydrolysis (IARC, 1991). It is available as 25% and 44% emulsifiable concentrate and 2.5% to 10% granules (HSDB , 2002). It is also available as a liquid formulation (IARC, 1991).
    B) SOURCES
    1) These herbicides are all synthetically manufactured. The 2,4-dihalo-3,4-dinitrobenzotrifluoride starting materials are prepared via nitration of the 2,4-dihalobenzotrifluoride with a mixture of fuming nitric and fuming sulfuric acids at a temperature below approximately 80 degrees C (HSDB , 2002).
    2) Benfluralin is made by nitration of chloro-4-trifluoromethylbenzene and reaction with butylethylamine (HSDB , 2002).
    C) USES
    1) These agents are selective pre-emergence dinitroaniline herbicides used against several annual grasses and many broad-leaf weeds. They affect seed germination and prevent weed growth by inhibition of root and shoot development (HSDB , 2002; Hartley & Kidd, 1987).
    2) Dinitroaniline herbicides, which interfere with microtubule dynamics, are being considered as possible candidates for human therapy of Chagas disease, caused by a protozoan parasite. In particular, trifluralin has been found effective against Leishmania, Trypanosoma brucei and several other protozoan parasites. Trifluralin has been shown to inhibit growth and differentiation of the malaria parasite, Plasmodium falciparum. Significant in vitro activity has been shown against Cryptosporidium parvum and Toxoplasma gondii (Traub-Cseko et al, 2001; Chan et al, 1993).

Overview

Life Support

    A) This overview assumes that basic life support measures have been instituted.

Clinical Effects

    0.2.1) SUMMARY OF EXPOSURE
    A) This class of herbicides is of relatively low toxicity to humans via all routes of exposure. Most of these herbicides are classified in WHO and EPA Toxicity as Class III. There has been little in the way of acute poisoning or adverse effects reported after human exposure despite wide usage. Animal studies have confirmed the relatively low toxicity in vertebrates.
    B) Ingestion of an herbicide formulation may result in nausea and vomiting and has resulted in aspiration pneumonitis. Reversible, mild CNS depression has occurred following ingestion. It is not known to what extent the surfactant, solvent or other ingredients contribute to toxicity. Prognosis is generally good following decontamination and symptomatic therapy.
    0.2.4) HEENT
    A) EYE IRRITATION - Although some herbicides in this class have caused eye irritation, oryzalin did not produce this effect when tested in rabbits.
    0.2.6) RESPIRATORY
    A) Ingestion of an herbicide formulation may result in aspiration pneumonitis.
    0.2.7) NEUROLOGIC
    A) Mild and reversible CNS depression may occur following systemic poisoning.
    0.2.8) GASTROINTESTINAL
    A) Nausea and vomiting may occur following ingestion of an herbicide formulation.
    0.2.14) DERMATOLOGIC
    A) Animal testing has shown these agents have mild irritant effects. These agents are NOT caustic.
    0.2.20) REPRODUCTIVE
    A) This group of herbicides is unlikely to cause reproductive effects in humans under normal circumstances. Teratogenic effects are not likely.
    B) Some studies have implicated oryzalin as an agent that might cause heart defects, but the relationship is not well documented.
    0.2.21) CARCINOGENICITY
    A) Some evidence suggests that the dinitroaniline herbicides are not carcinogenic. Metolachlor has shown some evidence of exposure response for lung cancer in pesticide applicators .

Laboratory Monitoring

    A) Dinitroaniline herbicide plasma levels are not clinically useful or readily available.
    B) Monitor vital signs and mental status following significant exposures.
    C) Following ingestions of herbicides in solvent formulations, monitor CBC, respiratory function and liver function tests for signs of toxicity due to the solvent.
    D) If severe vomiting and/or diarrhea occurs following ingestion of an herbicide formulation, monitor fluid and electrolyte levels.

Treatment Overview

    0.4.2) ORAL/PARENTERAL EXPOSURE
    A) There is no known antidote for dinitroaniline herbicide exposures. Treatment is SYMPTOMATIC and SUPPORTIVE. Toxicity is minimal. The major expected clinical effect is CNS depression, which should be monitored in all exposure cases.
    B) Ingestions of dinitroaniline herbicide formulations may result in clinical symptoms related to the surfactants, solvents or other ingredients, some of which may be corrosive. Treat symptomatically.
    C) Rinse the mouth and dilute with milk or water. For smaller ingestions, oral irrigation and dilution may be all that is necessary. Consider gastrointestinal decontamination only after large ingestions.
    1) Emesis is NOT recommended, although spontaneous vomiting may occur due to surfactants or solvents in the formulation.
    2) ACTIVATED CHARCOAL: Administer charcoal as a slurry (240 mL water/30 g charcoal). Usual dose: 25 to 100 g in adults/adolescents, 25 to 50 g in children (1 to 12 years), and 1 g/kg in infants less than 1 year old.
    D) Observe patients with ingestion carefully for the possible development of esophageal or gastrointestinal tract irritation or burns. If signs or symptoms of esophageal irritation or burns are present, consider endoscopy to determine the extent of injury.
    E) Rehydrate the patient losing fluids through vomiting and diarrhea. Fluid and electrolyte status should be carefully monitored.
    0.4.3) INHALATION EXPOSURE
    A) INHALATION: Move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with an inhaled beta2-adrenergic agonist. Consider systemic corticosteroids in patients with significant bronchospasm.
    0.4.4) EYE EXPOSURE
    A) DECONTAMINATION: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, the patient should be seen in a healthcare facility.
    0.4.5) DERMAL EXPOSURE
    A) OVERVIEW
    1) DECONTAMINATION: Remove contaminated clothing and jewelry and place them in plastic bags. Wash exposed areas with soap and water for 10 to 15 minutes with gentle sponging to avoid skin breakdown. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).

Range Of Toxicity

    A) Human toxicity data is minimal. Ingestion of 30 mL of pendimethalin has resulted in death from respiratory failure. Ingestion of 400 mL of pendimethalin has resulted in only moderate effects (intractable retching). In animal studies, evidence of increased locomotor activity has been reported at near-lethal doses of fluchloralin.
    B) ORYZALIN - LD50 for rats orally is greater than 10 g/kg and for dogs and cats it is greater than 1 g/kg.

Clinical Effects

Summary Of Exposure

    A) This class of herbicides is of relatively low toxicity to humans via all routes of exposure. Most of these herbicides are classified in WHO and EPA Toxicity as Class III. There has been little in the way of acute poisoning or adverse effects reported after human exposure despite wide usage. Animal studies have confirmed the relatively low toxicity in vertebrates.
    B) Ingestion of an herbicide formulation may result in nausea and vomiting and has resulted in aspiration pneumonitis. Reversible, mild CNS depression has occurred following ingestion. It is not known to what extent the surfactant, solvent or other ingredients contribute to toxicity. Prognosis is generally good following decontamination and symptomatic therapy.

Heent

    3.4.1) SUMMARY
    A) EYE IRRITATION - Although some herbicides in this class have caused eye irritation, oryzalin did not produce this effect when tested in rabbits.
    3.4.3) EYES
    A) IRRITATION - Oryzalin is not corrosive and did not cause irritation when applied to rabbit eyes (Hartley & Kidd, 1987). Other members of this group have shown minimal eye irritation (Gosselin et al, 1984). Eye application of benefin (benfluralin) to rabbits produced no irritation (HSDB , 2002).
    B) Conjunctivitis has been reported following eye exposure to pendimethalin herbicide formulation in a human (Chuang et al, 1998). Trifluralin and benefin (benfluralin) exposures have been shown to cause minimal eye irritation (Pentel et al, 1994).
    3.4.5) NOSE
    A) Inhalation of the dusts or fumes may result in mild to moderate irritation of the mucous membranes of the nose ((Anon, 1996)).
    3.4.6) THROAT
    A) Inhalation of the dusts or fumes may result in mild to moderate irritation of the mucous membranes of the mouth, nose, throat and lungs ((Anon, 1996)).

Respiratory

    3.6.1) SUMMARY
    A) Ingestion of an herbicide formulation may result in aspiration pneumonitis.
    3.6.2) CLINICAL EFFECTS
    A) INJURY OF UPPER RESPIRATORY TRACT
    1) Inhalation of the dusts or fumes may be mildly to moderately irritating to the upper respiratory tract ((Anon, 1996)).
    B) ASPIRATION PNEUMONITIS
    1) Ingestion of an herbicide formulation in solvent may result in aspiration pneumonitis. One death was reported following ingestion of an unknown amount of pendimethalin in a 50% xylene solvent formulation due to aspiration pneumonia. Respiratory failure and death was reported in another case following ingestion of about 30 mL, most likely due to the xylene (Chuang et al, 1998).

Neurologic

    3.7.1) SUMMARY
    A) Mild and reversible CNS depression may occur following systemic poisoning.
    3.7.2) CLINICAL EFFECTS
    A) CENTRAL NERVOUS SYSTEM DEFICIT
    1) Ingestion of a large amount of these herbicides may result in CNS depression. Coingestion of other chemicals, such as solvents, may contribute to initial consciousness disturbances (HSDB , 2002).
    2) CASE SERIES - In a review of 73 STOMP (pendimethalin and 50% xylene) ingestions, 5 patients were reported to have initial consciousness disturbance. No patient had neurological sequelae (Chuang et al, 1998).
    3.7.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) TREMOR
    a) When fluchloralin was administered dermally (up to 2000 mg/kg) or orally (up to 40 mg/kg) to mice, locomotor activity was significantly increased, with hyperexcitability and tremors. A 16.7% lethality rate was reported in mice that received dermal doses of 2000 mg/kg (HSDB , 2002).

Gastrointestinal

    3.8.1) SUMMARY
    A) Nausea and vomiting may occur following ingestion of an herbicide formulation.
    3.8.2) CLINICAL EFFECTS
    A) NAUSEA AND VOMITING
    1) Following ingestion of an herbicide in a solvent formulation, nausea, vomiting, diarrhea and epigastric pain may occur (HSDB , 2002; Chuang et al, 1998).
    3.8.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) DIARRHEA
    a) Mild salivation and diarrhea were reported in laboratory animals that were fed excessive amounts of nitralin (HSDB , 2002).
    2) VOMITING
    a) Large oral doses of oryzalin caused vomiting in dogs and cats (HSDB , 2002).

Genitourinary

    3.10.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) GLOMERULONEPHRITIS
    a) MICE - A feeding study of technical-grade trifuralin in female mice revealed progressive glomerulonephritis, with increases in BUN (IARC, 1991).

Hematologic

    3.13.2) CLINICAL EFFECTS
    A) METHEMOGLOBINEMIA
    1) LACK OF EFFECT
    a) Unlike dinitrobenzene, the dinitroaniline herbicides do NOT uncouple oxidative phosphorylation or generate methemoglobin in mammals or humans (HSDB , 2002; Chuang et al, 1998).

Dermatologic

    3.14.1) SUMMARY
    A) Animal testing has shown these agents have mild irritant effects. These agents are NOT caustic.
    3.14.2) CLINICAL EFFECTS
    A) SKIN IRRITATION
    1) These herbicides are rated as low toxicity by skin contact, but may cause mild to moderate skin irritation (O'Malley, 2001; Lewis & Sr, 1996; Pentel et al, 1994). They may cause skin sensitization in some susceptible individuals (HSDB , 2002). Dermal irritation was reported following skin contact in one case of pendimethalin exposure (Chuang et al, 1998).
    B) CONTACT DERMATITIS
    1) Contact dermatitis has been reported following dermal exposures to these herbicides. Allergic contact dermatitis (erythematous and pruritic dermatitis) was reported in a worker in a chemical pesticide company following exposures to trifluralin and benefin. Patch testing of the chemicals verified allergens (Pentel et al, 1994). Positive patch test reaction occurred with nitralin in a worker exposed to this chemical; he developed a pruritic eruption with scaly erythema (HSDB , 2002; Nishioka et al, 1983). Cross sensitization to chemically related structures within this group of herbicides may occur.
    3.14.3) ANIMAL EFFECTS
    A) ANIMAL STUDIES
    1) IRRITATION
    a) Testing in RABBITS showed oryzalin to be slightly irritating to the skin (Hartley & Kidd, 1987).

Reproductive

    3.20.1) SUMMARY
    A) This group of herbicides is unlikely to cause reproductive effects in humans under normal circumstances. Teratogenic effects are not likely.
    B) Some studies have implicated oryzalin as an agent that might cause heart defects, but the relationship is not well documented.
    3.20.2) TERATOGENICITY
    A) SKELETAL MALFORMATION
    1) MICE - Oral administration of trifluralin (1 g/kg body weight) to pregnant mice on days 6-15 of gestation resulted in an increased incidence of pups with pathological conditions. In the trifluralin-treated group, 12 out of 88 skeletal variants increased in frequency, with the most obvious being the occurrence of 14 ribs, parted frontals, an undoubled foramen ovale and accessory foramina in the cervical vertebrae (IARC, 1991).
    B) LACK OF EFFECT
    1) ANIMAL STUDIES
    a) Teratogenic and toxic effects on rat and rabbit fetuses have not been observed with pendimethalin or trifluralin ((Anon, 1996); Byrd et al, 1995).
    b) Oryzalin did not appear to demonstrate selective toxicity toward the developing conceptus in rat and rabbit studies. Treatment-related clinical signs of toxicity were not observed (HSDB , 2002).
    3.20.3) EFFECTS IN PREGNANCY
    A) HEART MALFORMATION
    1) HEART ABNORMALITIES - A study was done of 270 single pregnancies to wives of male workers at a plant manufacturing oryzalin. Each pregnancy was classified as to the exposure to oryzalin and pregnancy outcome. Of 15 pregnancies to workers actually exposed to oryzalin, three had heart malformation. The study group concluded there was an unusual cluster of birth defects, but could not decisively determine whether these defects were caused by occupational exposure to oryzalin (Gordon et al, 1985). Birth defects were not noted in another study done by Singal & Lee (1985).

Carcinogenicity

    3.21.1) IARC CATEGORY
    A) IARC Carcinogenicity Ratings for CAS19044-88-3 (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004):
    1) Not Listed
    3.21.2) SUMMARY/HUMAN
    A) Some evidence suggests that the dinitroaniline herbicides are not carcinogenic. Metolachlor has shown some evidence of exposure response for lung cancer in pesticide applicators .
    3.21.3) HUMAN STUDIES
    A) LUNG CANCER
    1) Metolachlor has shown some evidence of exposure response for lung cancer in pesticide applicators (Alavanja et al, 2004).
    3.21.4) ANIMAL STUDIES
    A) LACK OF EFFECT
    1) No carcinogenic response was noted in rats receiving dinitramine (100 or 300 mg/kg) orally in their diets for 2 years (HSDB , 2002).
    2) No increase in tumor formation was reported in mice given dietary doses of pendimethalin 75 mg/kg/day over an 18-month period ((Anon, 1996)).
    3) No remarkable non-neoplastic toxicity was reported in rats or mice in a carcinogenesis bioassay of trifluralin other than a low incidence of forestomach acanthosis and hyperkeratosis in mice. No increased incidence of neoplasms at any site in mice treated for 24 months was noted (IARC, 1991).

Genotoxicity

    A) Mutation data for oryzalin has been reported in the bacteria, S Typhimurium assays (RTECS, 2001; (Lewis & Sr, 1996).
    B) Mutagenic tests of pendimethalin, including tests on live animals and mammalian and bacterial cell cultures, have indicated no mutagenic activity ((Anon, 1996)).
    C) Genotoxic effects of trifluralin in cultured human peripheral blood lymphocytes have not been observed in chromosome aberrations and micronuclei assays. Clastogenic effects were not seen. A slight, but statistically significant, increase in the frequency of sister-chromatid exchanges was reported. The single-cell gel electrophoresis (SCGE) assay was used for the detection of DNA breaks (Ribas et al, 1996; Ribas et al, 1995).
    D) Cultured human lymphocytes were exposed to fluchloralin to assess chromosomal aberrations. Significant dose-dependent increase in total number of chromatid type aberrations was observed. A significant dose-dependent increase in number of micronucleated cells was noted (Panneerselvam et al, 1995).

Laboratory Monitoring

Monitoring Parameters Levels

    4.1.1) SUMMARY
    A) Dinitroaniline herbicide plasma levels are not clinically useful or readily available.
    B) Monitor vital signs and mental status following significant exposures.
    C) Following ingestions of herbicides in solvent formulations, monitor CBC, respiratory function and liver function tests for signs of toxicity due to the solvent.
    D) If severe vomiting and/or diarrhea occurs following ingestion of an herbicide formulation, monitor fluid and electrolyte levels.

Methods

    A) MULTIPLE ANALYTICAL METHODS
    1) Dinitroaniline herbicides have been detected by UV spectrophotometry, colorimetry, GLC, GC-FID, GC-ECD and gas chromatography-mass spectrometry (Kumazawa et al, 1995; Hartley & Kidd, 1987).
    2) Analysis of trace amounts of dinitroaniline herbicides in tissue and excreta has been described by a gas chromatography method, using electron capture detection. Recoveries of greater than 80% were reported over the concentration range of 0.1 to 1.0 mcg/g. Sensitivity of this method was estimated at 0.1 ppm for tissue samples and excreta. This method may be applied to humans when suspected exposure occurs (Edgerton et al, 1985).
    3) Oryzalin and its metabolites have been analyzed via high-pressure liquid chromatography in biological fluids (Dvorakova et al, 1997; Kennedy, 1977). A limit of detection for oryzalin of 0.1 mcg/mL and for depropyloryzalin of 0.01 mcg/mL has been reported (Dvorakova et al, 1997).
    4) Fluorine NMR spectroscopy has been used for the identification and quantitation of profluralin and its metabolites in biological fluids of rats following ingestion of the herbicide (Jacobson & Gerig, 1988).
    5) Kumazawa et al (1995) described gas chromatogram (GC) methods with ECD, SID, NPD, and FID for 300 pmol each of seven dinitroaniline herbicides (benfluralin, ethalfluralin, isopropalin, nitralin, pendimethalin, profluralin and trifluralin). GC with ECD was found to be most powerful for measurement of all dinitroaniline herbicides in human body fluids due to the high level of sensitivity and low background noise. Additionally, isopropalin could be detected by GC-SID with a sensitivity comparable to GC-ECD; high sensitivity was also obtained for isopropalin, pendimethalin, and nitralin using GC-NPD. GC-FID gave the lowest sensitivity.
    6) Guan et al (1998) reported a headspace solid-phase microextraction and gas chromatographic-electron capture detector determination of dinitroaniline herbicides in human blood, urine and environmental water. Herbicides measured included ethalfluralin, benfluralin, fluchloralin, prodiamine, isopropalin and pendimethalin. A reported linear range for the herbicides was 0.1 to 10 ng/mL for urine or water samples, and 1.0 to 60 ng/0.5 mL for whole blood.
    a) The authors recommend this method for use in forensic, clinical and environmental toxicology for analysis of dinitroaniline herbicides. Currently, no data on blood or urine concentrations of these herbicides in humans or animals after acute intoxication or chronic exposure are available.

Treatment

Life Support

    A) Support respiratory and cardiovascular function.

Patient Disposition

    6.3.1) DISPOSITION/ORAL EXPOSURE
    6.3.1.2) HOME CRITERIA/ORAL
    A) Exposure to dinitroaniline herbicides is generally NOT expected to result in significant toxicity. Asymptomatic children with accidental exposures can probably be managed safely at home with telephone follow up.
    6.3.1.5) OBSERVATION CRITERIA/ORAL
    A) Observe all patients following significant exposures to formulations containing toxic surfactants or solvents for at least 6 hours. Admit to hospital if severe vomiting and diarrhea occur; if vital signs are abnormal; or if acidosis, elevated liver function tests, renal insufficiency, impairment of consciousness or respiratory distress develops.
    6.3.3) DISPOSITION/INHALATION EXPOSURE
    6.3.3.1) ADMISSION CRITERIA/INHALATION
    A) Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.

Monitoring

    A) Dinitroaniline herbicide plasma levels are not clinically useful or readily available.
    B) Monitor vital signs and mental status following significant exposures.
    C) Following ingestions of herbicides in solvent formulations, monitor CBC, respiratory function and liver function tests for signs of toxicity due to the solvent.
    D) If severe vomiting and/or diarrhea occurs following ingestion of an herbicide formulation, monitor fluid and electrolyte levels.

Oral Exposure

    6.5.1) PREVENTION OF ABSORPTION/PREHOSPITAL
    A) SUMMARY
    1) Exposure to dinitroaniline herbicides is generally NOT expected to result in significant toxicity. Gastrointestinal decontamination should only be needed after large ingestions. For accidental ingestions in children rinsing the mouth, washing exposed skin and dilution with a few sips of water should be sufficient.
    B) EMESIS/NOT RECOMMENDED
    1) Emesis is not recommended, although spontaneous vomiting may occur due to surfactants, solvents or other ingredients in the herbicide formulation. Some ingredients in the formulation may be corrosive, causing esophageal injury.
    C) ACTIVATED CHARCOAL
    1) PREHOSPITAL ACTIVATED CHARCOAL ADMINISTRATION
    a) Consider prehospital administration of activated charcoal as an aqueous slurry in patients with a potentially toxic ingestion who are awake and able to protect their airway. Activated charcoal is most effective when administered within one hour of ingestion. Administration in the prehospital setting has the potential to significantly decrease the time from toxin ingestion to activated charcoal administration, although it has not been shown to affect outcome (Alaspaa et al, 2005; Thakore & Murphy, 2002; Spiller & Rogers, 2002).
    1) In patients who are at risk for the abrupt onset of seizures or mental status depression, activated charcoal should not be administered in the prehospital setting, due to the risk of aspiration in the event of spontaneous emesis.
    2) The addition of flavoring agents (cola drinks, chocolate milk, cherry syrup) to activated charcoal improves the palatability for children and may facilitate successful administration (Guenther Skokan et al, 2001; Dagnone et al, 2002).
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.2) PREVENTION OF ABSORPTION
    A) SUMMARY
    1) Exposure to dinitroaniline herbicides is generally NOT expected to result in significant toxicity. Gastrointestinal decontamination should only be needed after large ingestions. For accidental ingestions in children rinsing the mouth, washing exposed skin and dilution with a few sips of water should be sufficient.
    B) EMESIS/NOT RECOMMENDED
    1) Emesis is not recommended, although spontaneous vomiting may occur due to surfactants or solvents in the herbicide formulation. Solutions containing hydrocarbons may cause esophageal erosion.
    C) DILUTION
    1) DILUTION: If no respiratory compromise is present, administer milk or water as soon as possible after ingestion. Dilution may only be helpful if performed in the first seconds to minutes after ingestion. The ideal amount is unknown; no more than 8 ounces (240 mL) in adults and 4 ounces (120 mL) in children is recommended to minimize the risk of vomiting (Caravati, 2004).
    D) ACTIVATED CHARCOAL
    1) CHARCOAL ADMINISTRATION
    a) Consider administration of activated charcoal after a potentially toxic ingestion (Chyka et al, 2005). Administer charcoal as an aqueous slurry; most effective when administered within one hour of ingestion.
    2) CHARCOAL DOSE
    a) Use a minimum of 240 milliliters of water per 30 grams charcoal (FDA, 1985). Optimum dose not established; usual dose is 25 to 100 grams in adults and adolescents; 25 to 50 grams in children aged 1 to 12 years (or 0.5 to 1 gram/kilogram body weight) ; and 0.5 to 1 gram/kilogram in infants up to 1 year old (Chyka et al, 2005).
    1) Routine use of a cathartic with activated charcoal is NOT recommended as there is no evidence that cathartics reduce drug absorption and cathartics are known to cause adverse effects such as nausea, vomiting, abdominal cramps, electrolyte imbalances and occasionally hypotension (None Listed, 2004).
    b) ADVERSE EFFECTS/CONTRAINDICATIONS
    1) Complications: emesis, aspiration (Chyka et al, 2005). Aspiration may be complicated by acute respiratory failure, ARDS, bronchiolitis obliterans or chronic lung disease (Golej et al, 2001; Graff et al, 2002; Pollack et al, 1981; Harris & Filandrinos, 1993; Elliot et al, 1989; Rau et al, 1988; Golej et al, 2001; Graff et al, 2002). Refer to the ACTIVATED CHARCOAL/TREATMENT management for further information.
    2) Contraindications: unprotected airway (increases risk/severity of aspiration) , nonfunctioning gastrointestinal tract, uncontrolled vomiting, and ingestion of most hydrocarbons (Chyka et al, 2005).
    6.5.3) TREATMENT
    A) SUPPORT
    1) Dinitroaniline herbicides are of low order toxicity in mammals. Following a massive ingestion, CNS depression may occur. Treatment is symptomatic and supportive. Herbicide formulations may also contain surfactants, solvents, or other ingredients which may be more toxic than the dinitroaniline itself. It is important to elucidate which other toxic substances may be involved and treat accordingly.
    B) IRRIGATION
    1) Irrigate the mouth with water rinses.
    C) DILUTION
    1) DILUTION: If no respiratory compromise is present, administer milk or water as soon as possible after ingestion. Dilution may only be helpful if performed in the first seconds to minutes after ingestion. The ideal amount is unknown; no more than 8 ounces (240 mL) in adults and 4 ounces (120 mL) in children is recommended to minimize the risk of vomiting (Caravati, 2004).
    D) ENDOSCOPIC PROCEDURE
    1) Consider endoscopy in patients with signs or symptoms of mucous membrane irritation following ingestion of formulations containing corrosive solvents.
    E) FLUID/ELECTROLYTE BALANCE REGULATION
    1) Vomiting and diarrhea may be prolonged with large ingestions of herbicide formulations containing solvents, resulting in fluid and electrolyte loss. Monitor and replace as necessary.
    F) TELEPHONE CONSULTATION
    1) Provides consultation to poison centers and other health professionals for the management of pesticide poisoning. Calls will be transferred to the Oregon Poison Center in Portland, Oregon for all emergency cases requiring immediate medical response. The National Pesticide Telecommunications Network has a toll-free number, 1-800-858-7378, or if outside the U.S., the non-toll-free number is 541-737-6094. Hours are 6:30 to 4:40 PM PST Monday-Friday.

Inhalation Exposure

    6.7.1) DECONTAMINATION
    A) Move patient from the toxic environment to fresh air. Monitor for respiratory distress. If cough or difficulty in breathing develops, evaluate for hypoxia, respiratory tract irritation, bronchitis, or pneumonitis.
    B) OBSERVATION: Carefully observe patients with inhalation exposure for the development of any systemic signs or symptoms and administer symptomatic treatment as necessary.
    C) INITIAL TREATMENT: Administer 100% humidified supplemental oxygen, perform endotracheal intubation and provide assisted ventilation as required. Administer inhaled beta-2 adrenergic agonists, if bronchospasm develops. Consider systemic corticosteroids in patients with significant bronchospasm (National Heart,Lung,and Blood Institute, 2007). Exposed skin and eyes should be flushed with copious amounts of water.
    6.7.2) TREATMENT
    A) MONITORING OF PATIENT
    1) If respiratory tract irritation or respiratory depression is evident, monitor arterial blood gases, chest x-ray, and pulmonary function tests.
    B) Treatment should include recommendations listed in the ORAL EXPOSURE section when appropriate.

Eye Exposure

    6.8.1) DECONTAMINATION
    A) EYE IRRIGATION, ROUTINE: Remove contact lenses and irrigate exposed eyes with copious amounts of room temperature 0.9% saline or water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist after 15 minutes of irrigation, an ophthalmologic examination should be performed (Peate, 2007; Naradzay & Barish, 2006).

Dermal Exposure

    6.9.1) DECONTAMINATION
    A) DERMAL DECONTAMINATION
    1) DECONTAMINATION: Remove contaminated clothing and wash exposed area thoroughly with soap and water for 10 to 15 minutes. A physician may need to examine the area if irritation or pain persists (Burgess et al, 1999).
    6.9.2) TREATMENT
    A) IRRITATION SYMPTOM
    1) Treat dermal irritation or burns with standard topical therapy. Patients developing dermal hypersensitivity reactions may require treatment with systemic or topical corticosteroids or antihistamines.
    B) Treatment should include recommendations listed in the ORAL EXPOSURE section when appropriate.

Enhanced Elimination

    A) SUMMARY
    1) No studies have addressed the utilization of extracorporeal elimination techniques in poisoning with this group of herbicides.

Range Of Toxicity

Summary

    A) Human toxicity data is minimal. Ingestion of 30 mL of pendimethalin has resulted in death from respiratory failure. Ingestion of 400 mL of pendimethalin has resulted in only moderate effects (intractable retching). In animal studies, evidence of increased locomotor activity has been reported at near-lethal doses of fluchloralin.
    B) ORYZALIN - LD50 for rats orally is greater than 10 g/kg and for dogs and cats it is greater than 1 g/kg.

Minimum Lethal Exposure

    A) GENERAL/SUMMARY
    1) The minimum lethal human dose to any agent in this class of herbicides has not been delineated.
    2) In a series of 71 cases of pendimethalin poisoning there were 4 deaths from respiratory failure and/or aspiration pneumonitis. Fatalities were reported after ingestion of as little as 30 milliliters, although coingestants were likely involved (Cuang et al, 1998).
    B) ANIMAL DATA
    1) When fluchloralin was administered dermally (up to 2000 mg/kg) or orally (up to 40 mg/kg) to mice, locomotor activity was significantly increased, with hyperexcitability and tremors. A 16.7% lethality rate was reported in mice that received dermal doses of 2000 mg/kg (HSDB , 2002).

Maximum Tolerated Exposure

    A) GENERAL/SUMMARY
    1) The maximum tolerated human exposure to any agent in this class of herbicides has not been delineated.
    2) Chuang et al (1998) report a series of 71 cases of pendimethalin poisoning (64 deliberate ingestions, average ingestion 106.1 +/- 13.4 milliliters, range 3 to 400 milliliters). Twenty subjects (28%) were asymptomatic, 40 (56%) had mild signs and symptoms (headache, sore throat, dermal irritation, nausea, vomiting, abdominal pain), seven (9%) had moderate effects (intractable retching, hematemesis, initial altered mental status) and four (5%) had severe effects, most of whom were also intoxicated by other herbicides.
    B) ANIMAL DATA
    1) ORYZALIN - In a 2 year feeding trial done on rats, no adverse effects were seen when given 300 mg/kg (Hartley & Kidd, 1987).

Workplace Standards

    A) ACGIH TLV Values for CAS19044-88-3 (American Conference of Governmental Industrial Hygienists, 2010):
    1) Not Listed

    B) NIOSH REL and IDLH Values for CAS19044-88-3 (National Institute for Occupational Safety and Health, 2007):
    1) Not Listed

    C) Carcinogenicity Ratings for CAS19044-88-3 :
    1) ACGIH (American Conference of Governmental Industrial Hygienists, 2010): Not Listed
    2) EPA (U.S. Environmental Protection Agency, 2011): C ; Listed as: Oryzalin
    a) C : Possible human carcinogen.
    3) IARC (International Agency for Research on Cancer (IARC), 2016; International Agency for Research on Cancer, 2015; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2010a; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2008; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2007; IARC Working Group on the Evaluation of Carcinogenic Risks to Humans, 2006; IARC, 2004): Not Listed
    4) NIOSH (National Institute for Occupational Safety and Health, 2007): Not Listed
    5) MAK (DFG, 2002): Not Listed
    6) NTP (U.S. Department of Health and Human Services, Public Health Service, National Toxicology Project ): Not Listed

    D) OSHA PEL Values for CAS19044-88-3 (U.S. Occupational Safety, and Health Administration (OSHA), 2010):
    1) Not Listed

Toxicity Information

    7.7.1) TOXICITY VALUES
    A) LD50- (ORAL)MOUSE:
    1) >5 g/kg
    B) LD50- (ORAL)RAT:
    1) >10 g/kg
    C) LD50- (ORAL)RAT:
    1) 2500 mg/kg
    D) LD50- (ORAL)RAT:
    1) 3 g/kg
    E) LD50- (ORAL)MOUSE:
    1) >10 g/kg
    F) LD50- (ORAL)RAT:
    1) >10 g/kg
    G) LD50- (ORAL)MOUSE:
    1) 730 mg/kg
    H) LD50- (ORAL)RAT:
    1) 2940 mg/kg
    I) LD50- (SKIN)RAT:
    1) >4 g/kg
    J) LD50- (ORAL)MOUSE:
    1) >5 g/kg
    K) LD50- (ORAL)RAT:
    1) >5 g/kg
    L) LD50- (ORAL)MOUSE:
    1) >2 g/kg
    M) LD50- (ORAL)RAT:
    1) >2 g/kg
    N) LD50- (SKIN)RAT:
    1) >2 g/kg
    O) LD50- (ORAL)RAT:
    1) 10 g/kg
    P) LD50- (ORAL)MOUSE:
    1) 1340 mg/kg
    Q) LD50- (ORAL)RAT:
    1) 1050 mg/kg
    R) LD50- (ORAL)MOUSE:
    1) >15 g/kg
    S) LD50- (ORAL)RAT:
    1) 15380 mg/kg
    T) LD50- (SKIN)RAT:
    1) >2 g/kg
    U) LD50- (ORAL)RAT:
    1) 1808 mg/kg
    V) LD50- (SKIN)RAT:
    1) >3170 mg/kg
    W) LD50- (ORAL)MOUSE:
    1) 3197 mg/kg
    X) LD50- (ORAL)RAT:
    1) 1930 mg/kg
    Y) LD50- (SKIN)RAT:
    1) 5 g/kg

Pharmacology Toxicology

Pharmacologic Mechanism

    A) PLANTS - Inhibition of microtubule formation in algae and higher plants is the primary mechanism of action of dinitroaniline herbicides. These herbicides bind selectively free plant tubulin to form a complex that is incapable of polymerizing into microtubules (Traub-Cseko et al, 2001; Dvorakova et al, 1997). They affect the physiological processes necessary for seed germination (Hartley & Kidd, 1987). These herbicides do NOT inhibit microtubule function in animal cells (Dvorakova et al, 1997; Powis et al, 1997). They affect seed germination and prevent weed growth via inhibition of root and shoot development. They act by disrupting primary cell wall formation during cell division (HSDB , 2002).
    B) WHEAT - Oryzalin is a cytoskeleton-disrupting agent causing disassembly of microtubules in immature leaf sections. Cortical bands of microtubules and transverse hoops of wall reinforcement were not established following exposure of wheat leaf sections to oryzalin. Cell elongation and shaping was significantly impeded (Wernicke & Jung, 1992).
    C) PROTOZOA - Oryzalin, a microtubule-depolymerizing agent, contrary to expectations, caused an increase in alpha-tubulin synthesis and message level in the protozoan cells of Tetrahymena thermophilia. This is opposite of what is observed in mammalian cells (Stargell et al, 1992). Dinitroaniline herbicides, which interfere with microtubule dynamics, are being considered as possible candidates for human therapy of Chagas disease, caused by a protozoan parasite. In particular, trifluralin has been found effective against Leishmania, Trypanosoma brucei and several other protozoan parasites. Trifluralin has been shown to inhibit growth and differentiation of the malaria parasite, Plasmodium falciparum. Significant in vitro activity has been shown against Cryptosporidium parvum and Toxoplasma gondii. Trifluralin has been shown to be effective in-vivo, as a topical ointment, against L. major and Leishmania mexicana murine cutaneous leishmaniasis (Traub-Cseko et al, 2001; Chan et al, 1993).
    1) Oryzalin, ethalfluralin and other trifluralin appear to block replication of infectious T. gondii via disruption of the spindle-pole-body microtubules necessary for nuclear division, without altering the parasite's metabolism (Traub-Cseko et al, 2001; Stokkermans et al, 1996).
    2) Dinitroaniline herbicides appear to have a stronger effect on unstable microtubules, such as those going through an active process of depolymerization and polymerization. Microtubules involved in more dynamic processes, e.g., cytokinesis or endocytosis and organelle intracellular transport, seem to be the primary targets of the dinitroaniline drugs (Traub-Cseko et al, 2001).
    3) Due to low solubility of this group of herbicides, it is unlikely that they could be effective as systemic drugs; however, when delivered by topical formulations, trifluralin has been shown to be active against cutaneous Leishmania lesions in vivo (Stokkermans et al, 1996).
    D) MAMMALS - Oryzalin, and possibly other dinitroaniline herbicides, has been found to be an inhibitor of intracellular free Ca++ signaling in mammalian cells. It has also been found to have antitumor activity in mammals. An association was found between the ability to inhibit Ca++ signaling and inhibition of the growth of HT-29 human colon cancer cells and of CCRF-CEM human leukemia cells. When oryzalin was administered several days after tumor inoculation, no activity was seen against a panel of human tumor xenografts; antitumor activity was reported when oryzalin was given within 1 day of tumor inoculation. The in-vitro cytotoxicity of the major metabolite, N-depropyloryzalin, was similar to that of oryzalin (Dvorakova et al, 1997; Powis et al, 1997).

Physicochemical

Physical Characteristics

    A) BENFLURALIN is a yellow-orange crystalline solid with no appreciable odor (HSDB , 2002).
    B) DINITRAMINE is non-corrosive yellow crystals (HSDB , 2002).
    C) FLUCHLORALIN is an orange-yellow crystalline solid with faint medicinal odor (HSDB , 2002).
    D) ISOPROPALIN is a non-corrosive red-orange liquid (HSDB , 2002).
    E) NITRALIN is a golden-orange crystalline solid or a fine crystalline, light yellow to orange solid with a mild chemical odor (HSDB , 2002).
    F) ORYZALIN - This compound exists as yellow to orange crystals with no appreciable odor, or as a bright orange opaque liquid with a slight aromatic odor (HSDB , 2002; Budavari, 1996).
    G) PENDIMETHALIN is orange-yellow crystals with a fruit-like odor (HSDB , 2002). It is available in emulsifiable concentrate, wettable powder, or dispersible granule formulations ((Anon, 1996)).
    H) PROFLURALIN is yellow-orange crystals or liquid with no appreciable odor (HSDB , 2002).
    I) TRIFLURALIN - is yellow-orange crystals which is slightly soluble in water and freely soluble in common organic solvents, such as acetone. It is stable to hydrolysis (IARC, 1991).

Ph

    A) ORYZALIN - Very weak acid; pKa=9.4 (HSDB , 2002)

Molecular Weight

    1) Benfluralin: 335.32
    2) Butralin: 295.38
    3) Dinitramine: 322.28
    4) Ethalfluralin: 333.30
    5) Fluchloralin: 355.73
    6) Isopropalin: 309.41
    7) Nitralin: 345.41
    8) Oryzalin: 346.36
    9) Pendimethalin: 281.35
    10) Prodiamine: 350.34
    11) Profluralin: 347.33
    12) Trifluralin: 335.32

References

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