Dinitroaniline derivatives

DimethyItin dichloride lb 319 Dimetinden lb 354 Dinitramine lb 110-112 Dinitroaniline derivatives lb 111 Dinitroaniline herbicides lb 110,112... 

The step 4 product (1.0 mol) was converted into the corresponding dinitroaniline derivative by condensing with 2,4-dinitrofluoro benzene (1.0 mol) in dimethylformamide. 

Dinitroaniline herbicides. Trifluralin (Treflan ), a 4-trifluoromethyl substituted 2,6-dinitroaniline derivative, was the first main fluorine-containing herbicide to be marketed, with 18,000 tons sold in 1982 in the United States alone [16]. Trifluralin, which was introduced in 1960 by Eli Lilly, is a pre-emergence herbicide used in soybean for the control of a variety of grass and broadleaf weeds [17]. It is prepared from the nitration of 4-chlorobenzotrifluoride, followed by nucleophilic displacement of chlorine with di-n-propyl amine (Fig. 3). Following the success of trifluralin, a number of related A/,A/-dialkyl 4-trifluoromethyl 2,6-dinitroaniline herbicides were later introduced [18]. 

Urinary excretion of activity at 6 and 24 h after dosing accounted for 30% and 63%, respectively, of the administered dose. Fecal excretion over 3 days accounted for 23% of the dose. Elimination of 2,4-dinitroaniline-derived activity in the bile amounted to 12.5% of the dose after 5 h. 

The general formula of dinitroaniline derivatives with herbicidal properties is the following ... 

The more important dinitroaniline derivatives known today are N,N-bis(2-chloroethyl)-4-trifluoromethyl-2,6-dinitroaniline (BAS 3870 H, 1) N-butyl-N-ethyl-a,a,a-trifluoro-2,6-dinitro-p-toluidide (benfluralin, 2) N-jec-butyl-4-r-butyl-... 

Butralin is the sole dinitroaniline derivative in which the amino nitrogen carries only one substituent. It is interesting, on the other hand, that contrary to expectation, the N,N-di-5ec-butyl derivative exhibits no herbicidal activity. 

N,N DIPROP YL-4-TRIFLUORO-METHYL-2,6-DINITROANILINE (1582-09-8) Ci3HjsF3N304 Combustible solid (flash point >185 F/>85°C oc Fire rating 1). May react violently with barium, potassium, sodium. Incompatible with organic anhydrides, acrylates, alcohols, aldehydes, alkylene oxides, substituted allyls, cellulose nitrate, cresols, caprolactam solution, epichlorohydrin, ethylene dichloride, isocyanates, ketones, glycols, nitrates, phenols, vinyl acetate. Exothermic decomposition with maleic anhydride. May increase the explosive sensitivity of nitromethane. Reacts with nitroalkanes, forming explosive products. As a dinitroaniline derivative, the extremes of heat (do not store above 90°F/32°C), mechanical shock, and fnction might be... 

Dimethyltin dichloride 15 319 Dimetinden 15 354 Dinitiamine 15110-112 Dinitroaniline derivatives 15111 Dinitroaniline herbicides 15110,112... 

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