Pesticides aniline derivatives

Table VIII. Absorption Maxima of Some Aniline Derivative Pesticides and Related Compounds...

Various halogenated and nitrated aniline derivatives are used in the manufacture of dyestuffs and carbamate and urea based pesticides. Many of these compounds are suspected to be carcinogenic. 

The photoreactions characteristic for the halogenated phenols and anilines have shown to occur in most members of the series of chlorophenoxy and halophenylurea derivative pesticides, and in some other related biocides as well. Photohydrolysis is a frequently encountered process, but carbene formation has been demonstrated in several cases too. The phototransformation mechanisms of these molecules, however, are frequently complex, owing to the greater complexity of the molecules in question, and homolytic cleavage steps have been found to contribute in several cases. 

During the summer of 1982, the California Department of Food and Agriculture s Worker Health and Safety Unit staff monitored worker s exposure associated with the use of chlordimeform as pesticide on cotton in Imperial County, California, under a very tightly regulated exposure reduction program. Table IV gives a summary of chlordimeform (as aniline derivatives) measured in the urine of workers involved in applications of this pesticide. 

Most of these applications are in the area of water analysis for the determination of various pesticides, carboxylic and amino acids, aromatic compounds, surfactants, aniline derivatives, and metal ions. There are a few applications of SL membranes in soil and air analysis of carboxylic acids (Table 1). 

Eight carbamate pesticides were analyzed in bovine rumen. The method was based on extraction, partition, and an addititmal sweep condistillation step. This cleanup gave more re oducible results compared to cellulose-carbon column cleanup. The spots were visualized with either anisaldehyde or lV,2,6-trichloto-benzoquinoneimine after reversed-phase TLC (68). Carbamate and urea herbicides such as chlorpropham, metobromuron, and chlorbromuron were determined in medicinal plants by TLC. First they were hydrolyzed by alkali to 3-chloro-, 4-bromo-, and 3-chloro-4-bromoaniIines. These aniline derivatives were detected with 4-dimethylaminobenzaldehyde after TLC separation (Table 4) (69). Af-methyl carbamate pesticides can be separated by reversed-phase chromatography and analyzed by MS (70). 

Pesticides and pesticide metabolites e. g. aniline and urea derivatives [4]... 

Finally, a few miscellaneous compounds which were identified in the Delaware River and which have not been previously reported as water contaminants will be discussed Chloro (trifluoromethyl) aniline and chloro (trifluoromethyl) nitrobenzene (no. 55 and 56) were identified in the water, they had maximum concentrations at river mile 78. Both compounds represent common sub-structures in various pesticide and dye molecules, and several of the companies located along the river have patents using these compounds (30-32j. It is possible that these compounds are actually present in the river water as such, but it is also possible that they are formed in the GC injection port by pyrolytic degradation of larger pesticide or dye molecules (see above). All three binaphthyl-sulfone isomers (no. 92) were identified in the river water near Philadelphia. Product literature for one of the companies in the area indicates production of condensed sulfonated polymers derived from naphthalene sulfonic acid and maleic anhydride. It seems likely that the binaphthylsulfones are formed as by-products during preparation of this commercial product. 

After styrene production, approximately 20% of benzene production is used to produce cumene (isopropylbenzene), which is converted to phenol and acetone. Benzene is also converted to cyclohexane, which is used to produce nylon and synthetic fibers. Nitrobenzene derived from benzene is used to produce aniline, which has widespread use in dye production. Besides the benzene derivatives mentioned in this section, countless other products are based on the benzene ring. Cosmetics, drugs, pesticides, and petroleum products are just a few... 

Moreale, A., Van Bladel, R. (1976) Influence of soil properties on adsorption of pesticide-derived aniline and p-chloroaniline. J. Soil Sci. 27, 48-57. 

Bowman and Beroza [472] hydrolysed carbamates by heating with 10% NaOH solution and condensed the phenol produced with chlorothiophosphate in the presence of pyridine (Scheme 5.37). The resulting derivative is highly specific for the compound under analysis and, with the use of a flame photometric detector, it permits its sensitive analysis (at the level of hundredths of 1 ppm in foodstuffs). A column packed with 10% of DC-200 was used for the analysis at 190°C. Holden et al. [473] also obtained a high sensitivity in the analysis of N-methyl- and dimethylcarbamates if they condensed amines released by alkaline hydrolysis with l-fluoro-2,4-dinitrobenzene and applied an ECD for detection (2% of XE-60, 190°C). Different substituted anilines were similarly analysed as products from the decomposition of different pesticides [474] in the form of different perfluorinated acyl derivatives. 

Another group of compounds that can become enriched in soil or water comprises persistent organic chemicals, such as pesticides or other substances derived from chemical processes. Among these, halogenated ring systems are important pollutants. A research group at the Vienna University of Technology [37] has successfully screened several bacterial strains that are able to decompose chlorinated phenoxyalkanoates and anilines as well as phenolic compounds. 

The amine aniline is used in the production of dyes with deep shades of color. The common name aniline is derived from the plant in which it was historically obtained. Cyclohexylamine and ethylamine are important in the manufacture of pesticides, plastics, pharmaceuticals, and rubber that is used to make tires. 

In situ generated micelles have been applied to the inspection of aniline pesticidic metabolites in lake water. The separation of 16 PAH in SUA oligomer electrolytes was reported. Creosote-contaminated soil samples were extracted by accelerated solvent extraction using methylene chloride-acetone mixtures. The extracts were further fractioned by gel permeation chromatography before analysis. The EKC chromatogram of a creosote-contaminated soil fraction shows the resolution of at least 50 peaks. The separation of the 11 priority phenols in river and sea water was demonstrated in MEKC with DBTD surfactants, whereas examples of the use of liposomes as carriers include the separation of benzene derivatives and phenols." ... 

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