2- benzanilide moiety

The major metabolic pathways of flutolanil in plants are para-hydroxylation of the aniline ring and hydr-oxylation of the isopropoxy side chain. For potatoes, flutolanil anddesisopropyl-flutolanil (M-4) are selected as the target analytes. For rice plant, other metabolites containing 2-(trifluoromethyl)benzanilide moiety are also selected as the target analytes. For soil and water samples, flutolanil is selected as the only target analyte. 

Flutolanil and its metabolites containing the 2-(trifluoromethyl)benzanilide moiety are converted to methyl 2-(trifluoromethyl)benzoate (2-TFBA Me-ester) by alkaline hydrolysis and methylation for GC/MS analyses. 

Other studies on the PFR in the presence of cyclodextrins include substrates with different acyl moieties (phenyl propionate and phenyl valerate) [261] 1-naphthyl acetate [262,263], 1-naphthyl benzoate [263], sulfonate esters, [264,265], benzenesulfonylanilides [266], acetanilide [259,267], and benzanilide [259,268]. 

For the acid-catalysed hydrolysis of benzanilides substituted in the aromatic amine moiety p = 1.66. (8 ).The positive sign of the reaction constant can be easily understood in terms of the hydrolysis mechanism. The protonation of the carbonyl oxygen should not be very much affected by the polarity of a remote substituent in the N-ary 1 group. On the other hand, the rate of approach of a nucleophile depends upon the electrophilicity of the carbonyl carbon, which in turn is modified by the electron -releasing or electron - donating properties of the N-substituent. 

Substituents on the aromatic moiety of the acetanilide substrate substantially affect the efficiency of the coupling reaction (Table 2). As expected, ortho-substitution hampers the reaction. It has been reported that the palladation of ortho-substituted acetanilides does not occur [7] or occurs at elevated temperatures only [7b]. With N-m-tolylacetamide (6) the reaction efficiency is enhanced to give a 91 % yield of 14. Interestingly, reaction of N-methylanilide (10) gave no conversion at all. Formanilide and benzanilide (entries 7, 8) can be applied, although the yields are low to moderate. 

Acetophenones and benzyl phenyl ketones are arylated not only on the a-posi-tion, but also on the two orfho-positions using excess aryl bromides (Eq. 63) [129]. The reaction proceeds via a-arylation (see Sect. 2.2) followed by aromatic arylation. The latter seems to occur via coordination of the enolate oxygen to arylpalladium species, as in the reaction of 2-phenylphenols and 1-naphthols (Eqs. 56-58). Benzanilides are similarly diarylated on the benzoyl moiety using aryl bromides or triflates (Eq. 64) [130]. AT-Arylation [ 131 ] is not observed under the given conditions. 

Since, in homogeneous catalysis, the chemical nature of the amine moiety has a large influence on the hydrolysis rate [2,6,7], the previous conditions with zeolites were applied to several aromatic amides containing different substituents and to benzanilide. 

In benzoic acid anilide (benzanilide, 353 X = Y = H), the phenyl ring A is relatively deactivated towards electrophilic substitution by the attached carbonyl group as compared with ring B, which is activated by the amino moiety, so sulfonation of benzanilide occurs selectively in ring B. 

In 2008, Fagnou et al. reported that acetanilide couples with alkynes in the presence of a Cp Rh catalyst and a copper salt oxidant through ortho C—H bond cleavage to produce Al-acetylindole derivatives [Eq. (a) in Scheme 25.36] [28a]. In contrast, the authors found that benzanilide, which possesses two types of cleavable ortho C—H bonds on anilino and benzoyl moieties, undergoes annulation accompanied by the selective cleavage of the benzoyl C—H bond to give isoquinolinone derivatives [Eq. b] [20]. 

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