25057-89-0 Usage
Description
Bentazon is unique under these herbicides
because it is the only compound that bears a sulfonyl
group. A puzzle that is not solved yet is that bentazone
is an excellent herbicide but has a very low pI50-value.
Chemical Properties
Bentazon is a colorless to white crystalline
powder.
Uses
Different sources of media describe the Uses of 25057-89-0 differently. You can refer to the following data:
1. Herbicide.
2. Selective, contact, postemergence herbicide used to control a variety of annual and
perennial broad-leaved weeds in most grass and legume crops.
Definition
ChEBI: A benzothiadiazine that is 1H-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide substituted by an isopropyl group at position 3.
Agricultural Uses
Selective post-emergent herbicide: A post-emergence herbicide used to control broadleaf
weeds in crops such as beans, corn, mint, soybeans,
rice, and peanuts. All products formerly marketed in the
U.S. contain the sodium salt of bentazon as the active ingredient, referred to as sodium bentazon. Also used in
selective post-emergent control of broadlelaf weeds and
sedges in alfalfa, asparagus, cereals, clover, digitalis, dry
peas, flax, garlic, grasses, green lima beans, mint, onions,
potatoes, snap beans for seed, sorghum, soybeans and sugarcane.
Not currently registered in the U.S. It is reported to
be used in most European countries.
Trade name
ASAGIO?; BAS 351-H?; BASAGRAN?;
BENDIOXIDE?; BENTA?; BLAST?; ENTRY?;
LADDOK?; LEADER?; PLEDGE?; STORM?
Safety Profile
Moderately toxic by
ingestion and skin contact. An experimental
teratogen. Other experimental reproductive
effects. When heated to decomposition it
emits very toxic fumes of SO, and NOx.
Potential Exposure
A potential danger to those involved
in the manufacture, formulation or application of this selective
postemergent thiadiazine herbicide.
Environmental Fate
Soil. Under aerobic conditions, bentazone was reported to degrade to 6- and 8-hydrox ybentazone compounds. In addition, anthranilic acid and isopropylamide were reported
as soil hydrolysis products (Otto et al., 1978). Persistence in soil is less than 6 weeks
(Hartley and Kidd, 1987). Bentazone is readily adsorbed onto organic carbon and therefore,
is not expected to leach to groundwater (Abernathy and Wax, 1973). The dissipation half life of bentazone in field soil is 5 days (Ross et al., 1989).Plant. Undergoes hydroxylation of the aromatic ring and subsequent conju-gation in
plants (Otto et al., 1978; Hartley and Kidd, 1987) forming 6- and 8-hydroxybentazone
compounds (Otto et al., 1978). The half-life in and/or on plants is 2–3 days (Photolytic. Humburg et al. (1989) reported that 30% degradation of bentazone on glass
plates occurred when exposed to UV light (λ = 200–400 nm); however, no photoproduct(s)
were reported. The natural sunlight and simulated sunlight irradiation ofChiron et al. (1995) investigated the photodegradation of bentazone (20 μg/L) in
distilled water and Ebro River water using an xenon arc irradiation. In distilled water,
bentazone completely disappeared after 16 hours of irradiation. Photodegradation appeared
to follow pseudo-first-order kinetics with a half-life of about 2.5 hours. The presence of
humic substances (4 mg/L) increased the rate of photodegradation and the disappearance
of bentazone was achieved in 8 hours. No significant breakdown photoproducts were
identified.
Metabolic pathway
14C-Bentazon degrades in soils under conventional
tillage and no-tillage (3-18 years) with varying
histories of bentazon application. The half-life for
bentazon degradation ranges from 4.6 to 49.5 days;
half-lives for some no-tillage soils with the longest
histories of application are lower than those of
conventional tillage soils. Half-lives for soils with no
bentazon history are 3-11 times higher than the half-
lives of those previously exposed to bentazon. N-
Methylbentazon is the most consistently observed
metabolite. The other metabolites identified in soils
result from hydroxylation on the phenyl ring and the
cleavage of the benzothiadiazine ring, yielding 6- and
8-hydroxybentazons and anthranilic acid via
2-amino-N-isopropylbenzamide.
Incompatibilities
Keep away from flammable materials,
heat and flame. Risk of fire and explosion if formulations
contain flammable/explosive solvents.
Waste Disposal
In accordance with
40CFR165, follow recommendations for the disposal of
pesticides and pesticide containers. Must be disposed properly
by following package label directions or by contacting
your local or federal environmental control agency, or by
contacting your regional EPA office.
Check Digit Verification of cas no
The CAS Registry Mumber 25057-89-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,5,0,5 and 7 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 25057-89:
(7*2)+(6*5)+(5*0)+(4*5)+(3*7)+(2*8)+(1*9)=110
110 % 10 = 0
So 25057-89-0 is a valid CAS Registry Number.
InChI:InChI=1/C10H12N2O3S/c1-7(2)12-10(13)8-5-3-4-6-9(8)11-16(12,14)15/h3-7,11H,1-2H3
25057-89-0Relevant articles and documents
2,1,3-Benzothiadiazine derivatives: Synthesis and screening versus PDE4 enzyme
Tait, Annalisa,Luppi, Amedeo,Avallone, Rossella,Baraldi, Mario
, p. 653 - 663 (2007/10/03)
A series of N-1,3 disubstituted 2,1,3-benzothiadiazine derivatives (BTDs) were synthesized and evaluated for their inhibitory activity versus enzymatic isoform PDE4 extracted from U937 cell line. Some of the tested compounds showed a high PDE4 inhibitory activity at 100:μM and the IC50 value of the most interesting terms were evaluated. The structure-activity relationships of these compounds showed that the 3,5-di-tert-butyl-4-hydroxybenzyl moiety at N-1 position is important to obtain activity at micromolar level as previously reported. For the same compounds the antioxidant activity were evaluated highlighting 14 as the most significative one. The introduction of other bulky substituents in N-1 position is detrimental.
Method for the production of 3-isopropyl-1H-2, 1,3-benzothiadiazine-4 (3H)-one-2,2-dioxide
-
, (2008/06/13)
A process for preparing 3-isopropyl-1H-2,1,3-benzothiadiazin-4 (3H)-one 2,2-dioxide (I) or a salt of I which comprises reacting anthranilic isopropylamide II simultaneously with sulfur trioxide or chlorosulfonic acid in the presence of an organic base or with adducts of sulfur trioxide and organic bases and phosphorus oxychloride at from 50° C. to the reflux temperature, followed, if appropriate, by conversion into its salts, is described.
Herbicidal mixtures having a synergistic effect
-
, (2008/06/13)
PCT No. PCT/EP96/03996 Sec. 371 Date Feb. 17, 1998 Sec. 102(e) Date Feb. 17, 1998 PCT Filed Sep. 12, 1996 PCT Pub. No. WO97/10714 PCT Pub. Date Mar. 27, 1997A composition comprising at least one sulfonylurea of the formula I wherein R1 is substituted alkyl; halogen; a group ER6 (E=O, S or NR7); COOR8; NO2; S(O)oR9; SO2NR10R11; or CONR10R11; R2 is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, haloalkoxy, haloalkyl, alkylsulfonyl, nitro, cyano or alkylthio; R3 is F, CF3, CF2Cl, CF2H, OCF3, OCF2Cl, or, if R1 is CO2CH3 and R2 is simultaneously fluorine, R3 is Cl, or, if R1 is CH2CF3 or CF2CF3, R3 is methyl, or, if R4 is OCF3 or OCF2Cl, R3 is OCF2H or OCF2Br; R4 is alkoxy, alkyl, alkylthio, alkylamino, dialkylamino, halogen, haloalkyl or haloalkoxy; and R5 is hydrogen, alkoxy or alkyl; or an enviromentally compatible salt of I, and an aryloxyalkanoic acid selected from the group consisting of 2,4-D, 2,4-DB, clomeprop, dichlorprop, dichlorprop-P, dichlorprop-P (2,4-DP-P), fenoprop (2,4,5-TP), fluoroxypyr, MCPA, MCPB, mecoprop, mecoprop-P, napropamide, napropanilide, triclopyr, and an enviromentally compatible salt thereof exhibits a synergistic herbicidal effect.
