1861-40-1 Usage
Description
Benfluralin, also known as a preemergent dinitroaniline herbicide, is a yellow-orange solid that has been registered in the United States since 1970. It is a tertiany amino compound that is 2,6-dinitro-4-(trifluoromethyl)aniline in which the hydrogens attached to the aniline nitrogen have been replaced by one ethyl and one butyl group. Benfluralin is used for the control of a wide range of annual grass and broadleaf weeds in various crops.
Uses
Used in Agriculture:
Benfluralin is used as a selective pre-emergence herbicide for the control of annual grasses and broad-leaf weeds in various crops such as groundnuts, tobacco, lettuce, turf, alfalfa, clover, watermelons, and sweet melons. It is particularly effective against target species like Johnson grass seedlings, chickweed, lamb quarters, purslane, knotweed, clover, and barnyard grass. Benfluralin affects seed germination and prevents weed growth by inhibiting root development. It is absorbed by roots and disrupts cell division by binding to tubulin, thereby inhibiting microtubule formation and leading to microfibril disorientation.
Used in Commercial and Residential Applications:
Benfluralin is used as a preemergent herbicide to control monocot and dicot weeded species in commercial and residential applications. It can be used alone or formulated with other structurally related preemergent herbicides such as oryzalin, isoxaben, triclopyr, and/or trifluralin. Various formulated types include emulsifiable concentrate, granules, soluble concentrate/liquid, and water dispersed granules. Benfluralin is formulated as granules in 42 end-use products and one product in the form of water dispersible granules. Applications can be by broadcast (granules and fertilizer mixed) and band treatment, golf course treatment, soil incorporated treatment, and spray with ground/sprinkler irrigation systems.
Used in Vegetables and Turf:
Benfluralin is used as a trifluoromethyl dinitroaniline selective preemergence herbicide for the control of annual grasses and some broad-leaved weeds in vegetables and turf. It is also used on crops such as alfalfa, red clover, seeded lettuce, trefoil, peanuts, certain tobaccos, and vegetables like endive, field and French beans, and lentils.
Air & Water Reactions
Slightly water soluble.
Reactivity Profile
A dinitroaniline derivative.
Hazard
Highly toxic.
Trade name
BALAN?; BALFIN?; BENEFEX?;
BETHRODINE?; BHULAN?; BINNELL?;
BONALAN?; CARPIDOR?; EL-110?; EMBLEM?;
FLUBALEX?; PEL-TECH?; QUILAN?; TEAM; XL 2G
Chemical class: 2,6-Dinitroaniline
Potential Exposure
Selective preemergence herbicide used
to control of annual grasses and broad-leaf weeds. Used on
alfalfa, red clover, seeded lettuce, trefoil; peanuts, certain
tobaccos, vegetables such as endive, field and French
beans, and lentils. A dinitroaniline derivative.
Environmental Fate
Soil. Benfluralin degraded faster in flooded soils under anaerobic conditions than when
oxygen was present. The major route of benfluralin degradation in flooded soil is the
formation of polar products (Golab et al., 1970) including N-butyl-N-ethyl-α,α,α-trifluoro-
5-nitrotoluene-3,4-diamine, N-butyl-N-ethyl-α,α,α-trifluorotoluene-3,4,5-triamine, N butyl-N-ethyl-α,α,α-trifluorotoluene-3,4,5-triamine, N-butyl-α,α,α-trifluoro-2,6-dinitro p-toluidine, N-ethyl-α,α,α-trifluoro-2,6-dinitro-p-toluidine, N-butyl-α,α,α-trifluoro-5-
nitrotoluene-3,4-diamine, N-butyl-α,α,α-trifluorotoluene-3,4,5-triamine, N-ethyl-α,α,α-
trifluoro-5-nitrotoluene-3,4-diamine, α,α,α-trifluoro-5-nitrotoluene-3,4-diamine, and
α,α,α-trifluorotoluene-3,4,5-triamine (Williams, 1977). The rate of degradation was high est under anaerobic conditions.Nash (1988) reported a dissipation half-life of 2 days for benfluralin in soil.Photolytic. Though no products were identified, benfluralin is subject to photodegra dation by UV light (Worthing and Hance, 1991). A photodegradation yield of 79% was
achieved after the herbicide in dry soil was subjected to sunlight for 7 daysChemical/Physical. In aqueous solutions (pH 5–9 and 26°C), benfluralin is stable up
to 30 days (Worthing and Hance, 1991).
Shipping
UN3077 Environmentally hazardous substances,
solid, n.o.s., Hazard class: 9; Labels: 9—Miscellaneous
hazardous material, Technical Name Required. UN1596
Dinotoanilines, Hazard Class: 6.1; Labels: 6.1—Poisonous
materials.
Toxicity evaluation
Use of benfluralin as a preemergent herbicide results in
a direct release into the environment. Benfluralin has an
estimated Henry’s law constant of 2.91×10-4 atm-m3mol-1
derived from a vapor pressure of 6.6×105 mmHg. Benfluralin
has a water solubility of 0.1 mg l-1, an octanol/water
partition coefficient of Kow = 5.29 and a soil organic carbon–
water partitioning coefficient range of Koc= 9840 to
11660.
Based on the Henry’s law constant, volatilization of benfluralin
from moist soil surfaces and water surfaces is expected.
However, volatilization of benfluralin from dry soil surface is
not expected. Benfluralin is typically formulated and applied to
minimize volatilization. Benfluralin Koc value range indicates
a decreased mobility in soil. The Koc value also indicates that
benfluralin can be expected to adsorb to suspended solids and
sediment in the water column.
Incompatibilities
Incompatible with oxidizers (chlorates,
nitrates, peroxides, permanganates, perchlorates, chlorine,
bromine, fluorine, etc.); contact may cause fires or explosions.
Keep away from alkaline materials, strong bases,
strong acids, oxoacids, epoxides. Moderate heat causes
decomposition that produces toxic vapors that can form an
explosive mixture with air.
Waste Disposal
Do not discharge into drains
or sewers. Dispose of waste material as hazardous waste
using a licensed disposal contractor to an approved landfill.
Consult with environmental regulatory agencies for guidance
on acceptable disposal practices. If allowed,
Incineration with effluent gas scrubbing is recommended.
Containers must be disposed of properly by following package
label directions or by contacting your local or federal
environmental control agency, or by contacting your
regional EPA office. Ultraviolet-radiation: This liquid herbicide
is reported to be susceptible to decomposition by
UV radiation.
Check Digit Verification of cas no
The CAS Registry Mumber 1861-40-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,8,6 and 1 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1861-40:
(6*1)+(5*8)+(4*6)+(3*1)+(2*4)+(1*0)=81
81 % 10 = 1
So 1861-40-1 is a valid CAS Registry Number.
InChI:InChI=1/C13H16F3N3O4/c1-3-5-6-17(4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3
1861-40-1Relevant articles and documents
Regioselectivity and stereoelectronic effects in the reactions of the dinitroaniline herbicides trifluralin and benefin with nucleophiles
Annandale, Michael T.,VanLoon, Gary W.,Buncel, Erwin
, p. 873 - 883 (2007/10/03)
The reactions of two members of the dinitroaniline class of herbicides, N,N-di-n-propyl-2,6-dinitro-4-(trifluoromethyl)aniline (trifluralin; 1) and N-ethyl-N-n-butyl-2,6-dinitro-4-(trifluoromethyl)aniline (benefin; 2), along with their analogue, N-phenyl-2,6-dinitro-4-(trifluoromethyl)aniline (3), with the nucleophiles, OD- and SO32-, have been investigated using 400 MHz 1H NMR spectroscopy. The reactions of both 1 and 2 with OD- result in formation of Meisenheimer anionic σ-complexes according to a K3T1 (kinetic preference for formation of the C-3 adduct with thermodynamic preference for formation of the C-1 adduct) reaction sequence while the reaction of 3 with OD- and that of 1 with SO32- follow a K3T3 (kinetic and thermodynamic preference for formation of the C-3 adduct) sequence. There was no observation of the C-1 adducts of 1 and 2 with OD-, but the products of S(N)Ar displacement at C-1 were observed as the final thermodynamic products. Geometry optimization calculations support our hypothesis of n → σ* stabilization of the C-1 adduct leading to S(N)Ar displacement. In the reaction of 3 with OD-, initial N-deprotonation to form the anion, 3a, is followed by σ-complex formation. The final thermodynamic product observed in this system is 3,5-dinitro-4-(N-phenylamino)benzoic acid formed through hydrolysis of the trifluoromethyl group on the anion, 3a. Aryl H-D exchange has been found for the systems of 1 and 2 with OD-, but not for the SO32- system and neither for the reaction of 3 with OD-. Since dimethylpicramide showed significantly slower H-D exchange under identical conditions, it is argued that this discrepancy has as origin the ability of the amino N lone electron pair to interact with the π-system of the ring. With both 1 and 2 the larger size of the amino alkyl chains prevent the amino N lone pair from aligning with the π-system of the ring, thus hindering electron density donation to the electron-deficient ring carbons.
4-Trifluoromethyl-2,6-dinitroanilines
-
, (2008/06/13)
This invention relates to a group of novel substituent anilines, useful in eliminating germinating and seedling weed grasses and selected broadleaf weeds.
Plant-protective and pest-control agent
-
, (2008/06/13)
A herbicidal composition capable of preventing weed growth of potatoes or soybean plants consists of a triazene or an aromatic nitro compound together with an inorganic salt, especially sodium bisulfate or potassium bisulfate which reduced the quantity of the organic herbicide below that usually required to obtain a corresponding herbicidal effect and hence prevents phytotoxic damage. The composition contains 0.1:1 to 15:1 parts by weight of the inorganic compound to the organic compound and is applied in an amount of 0.1 to 30 kg of the composition per hectare.
