Dinitrophenol herbicide

Stemmler EA, Hites RA. 1987. The electron capture negative ion mass spectra of 2,6-dinitroaniline and 2,4-dinitrophenol herbicides and related nitrobenzene derivatives. Biomed Environ Mass Spectrom 14 417-434. 

Wallnoefer PR, Ziegler W, Engelhart J, et al. 1978. Transformation of dinitrophenol herbicide by Azobacter sp. Chemosphere 12 967-972. 

Figure 5 Calibration curves for the dinitrophenol herbicide DNOC in aqueous solution when using different techniques (A) PDS Photothermal deflection spectroscopy, (B) TL thermal leasing, (C) PIS Photothermal Interferometric spectroscopy, (D) PAS a photoacoustic spectroscopy, (E) a conventional spectrophotometer Cary 2400. Reproduced with permission of SPIE from Faubel W (1997) Detection of pollutants in liquids and gases. In Mandelis A and Hess P (eds) Life and Earth Sciences. Progress in Photothermal and Photoacoustic Science and Technology, Vol III, Chapter 8. Bellingham SPIE.

Up until 1986 the major use for 2-j -butylphenol was in the production of the herbicide, 2-j -butyl-4,6-dinitrophenol [88-85-7] which was used as a pre- and postemergent herbicide and as a defoHant for potatoes (30). The EPA banned its use in October 1986 based on a European study which showed that workers who came in contact with 2-j -butyl-4,6-dinitrophenol experienced an abnormally high rate of reproduction problems. Erance and the Netherlands followed with a ban in 1991. A significant volume of 2-j -butyl-4,6-dinitrophenol is used worldwide as a polymerization inhibitor in the production of styrene where it is added to the reboiler of the styrene distillation tower to prevent the formation of polystyrene (31). OSBP is used in the Par East as the carbamate derivative, 2-j -butylphenyl-Ai-methylcarbamate [3766-81-2] (BPMC) (32). BPMC is an insecticide used against leaf hoppers which affect the rice fields. 

Another factor that can influence the environmental distribution of a chemical is the presence of charged groups. Some pollutants, such as the sodium or potassium salts of phenoxyalkanoic herbicides, dinitrophenols, and tetra- or penta-chlo-rophenol, exist as anions in solution. Others, such as the bipyridyl herbicides diquat and paraquat, are present as cations. In either case, the ions may become bound to organic macromolecules or minerals of soils or sediments that bear the opposite... 

Nitrophenols are phytotoxic, and dinoseb (6-iec-butyl-2,4-dinitrophenol) has been used as a herbicide, while nitrophenols have been detected in rainwater and plausible mechanisms for their abiotic formation have been proposed (Kohler and Heeb 2003 Vione et al. 2005). The pathway for the degradation of phenols with a single nitro group depends on the position of the substituents, while... 

Kaake RH, DJ Roberts, TO Stevens, RL Crawford, DL Crawford (1992) Bioremediation of soils contaminated with the herbicide 2-5ec-butyl-4,6-dinitrophenol (Dinoseb). Appl Environ Microbiol 58 1683-1689. 

One of the major problems in rice production is grass control. Various grasses compete with rice and drastically reduce yields. Results of preliminary experiments in Venezuela (9) indicate that rice yields may be increased by the application of dinitrophenol as a pre-emergence herbicide, even though rice stands are reduced by this chemical. Additional research is needed in this field, as the possibility exists... 

CF 2, see 1,1,1-Trichloroethane CFC 11, see Trichlorofluoromethane CFC 21, see Dichlorofluoromethane CFC 112, see 1,2-Difluorotetrachloroethane CFC 112a, see 1,1-Difluorotetrachloroethane CFC 113, see 1,1,2-Trichlorotrifluoroethane Chelen, see Chloroethane Chemform, see Methoxychlor Chemathion, see Malathion Chemical 109, see ANTU Chemical mace, see a-Chloroacetophenone Chemox PE, see 2,4-Dinitrophenol Chempenta, see Pentachlorophenol Chemphene, see Toxaphene Chemrat, see Pindone Chemsect DNOC, see 4,6-Dinitro-ocresol Chemtol, see Pentachlorophenol Chevron acetone, see Acetone Chimec NR, see 2-Bntoxyethanol Chinone, see / Qninone Chinnfnr, see Carbofuran Chipco thiram 75, see Thiram Chipco turf herbicide "D", see 2,4-D Chladone 11, see Trichlorofluoromethane Chlon, see Pentachlorophenol Chlorallylene, see Allyl chloride Chloran, see Lindane 4-Chloraniline, see 4-Chloroaniline p-Chloraniline, see 4-Chloroaniline Chlorbenzene, see Chlorobenzene Chlorbenzol, see Chlorobenzene p-Chlor-ro-cresol, see p-Chloro-ro-cresol Chlordantoin, see Amyl acetate Chlordan, see Chlordane... 

Dinitrophenols had been used as insecticides since 1892 but it was not until the 1930s that their value as herbicides was discovered and 4,6-dinitro-o-cresol (DNOC) was introduced. The trouble with dinitrophenols was their toxicity to all living organisms that respire. Their mode of action is through the uncoupling of oxidative phosphorylation, an effect that leads to a rapid death of any organism that comes into contact with the chemical, including the operator. 

Estimate the Kiow values at 25°C of (a) ethylacetate, (b) 2,3,7,8-tetrachloro-dibenzodioxin, (c) the herbicide 2-s-butyl-4,6-dinitrophenol (Dinoseb), (d) the insecticide parathion, and (e) the hormone testosterone using solely the fragment coefficients and correction factors given in Tables 7.4 and 7.5 (Eq. 7-15). 

Figure 10.15 Plot of log 1 /LCi50 for guppies versus (a) log octanol-water distribution ratio (log Z),ow, Eq. 10-41), and (b) log liposome-water distribution ratio (log Z),lipsw, Eq. 10-41) at pH 7 for a series of chlorinated benzenes (o) and chlorinated phenols ( ) as well as for the herbicide 2-.9ec-butyl-4.6-dinitrophenol (dinoseb) (v). The liposomes used were L-a-dimy-ristoyl-phosphatidylcholine (chlorinated benzenes) and L-a-dioleyl-phosphatidylcholine (chlorinated phenols and dinoseb). The pH dependence of D/ow and D,lipsw of pentachlorophenol (PCP) and dinoseb is shown in Fig. 10.14. Data from Saarikoski and Viluskela (1992), Gobas et al. (1988), Escher and Schwarzenbach (1996), and Gunatilleka and Poole (1999).

Dr Otto Borgmann obtd patents in 1893 for the manuf of expls contg salts or additive compds similar to those produced from Dinitrophenols (cited in Ref 4). The shock sensitiveness of Dinitrocresols, and a number of other expls, was detd by Wohler Wenzelberg (Ref 6a). In addn to their use as expls, Dinitrocresols have been used in selective herbicides insecticides (Ref 11). See also Cresylates Refs l) Beil 6, 368, (180) [34ll 2) Beil 6,... 

Dinitrophenol was used in explosives during World War I. It was used as an insecticide and an herbicide. It was also a popular weight loss remedy 100,000 people took dinitrophenol in 1936. 

DNOC (4,6 -dinitro-o-cresol) is one of a group of dinitrophenol and dinitrocresol herbicides that are highly toxic to both humans and animals. Most compounds in this class are well absorbed from the GI tract, via the skin and by the lung (as fine droplets). 

In addition to the most popular chlorophenoxy herbicides, the group includes a variety of other chemical classes—e.g., amides, bipyridyls, carbamates, dinitrophenols, substituted ureas and triazines. Most of the chemicals tested are animal teratogens, as are many of the fungicides in this miscellaneous group (ref. 185. p. 578 and 586). 

Herbicides are chemicals used to destroy unwanted plants (terrestrial or aquatic) called weeds. Herbicides fall into two broad categories inorganic (e.g., copper sulfate, sodium chlorate, and sodium arsenite) and organic (e.g., chlorophenoxy compounds, dinitrophenols, bipyridyl compounds, carbamates, and amide herbicides). Historically, inorganic compounds were the first available and the first used. There has been over a long period a continuous effort to develop herbicide compounds that are more selective—that affect weeds, as opposed to desirable plants. 

Some good inhibitors of the Hill reaction, however, do not contain the carbonyl oxygen-nitrogen moiety. Examples are the dinitroanilines, diphenylethers, 2,4-dinitrophenols, halogenated benzonitriles, and pyridinols. Hence, the postulates proposed are not all inclusive. Three of these herbicides are phenols. Under physiological pH s, the molecules can be expected to be ionized, and it may be the ionized form of the molecule that binds to the receptor. 

Broholm M. M., Tuxen N., Riigge K., and Bjerg P. L. (2001) Sorption and degradation of the herbicide 2-methyl-4,6-dinitrophenol under aerobic conditions in a sandy aquifer in Vejen, Denmark. Environ. Sci. Technol. 35(24), 4789-4797. 

Dinitrophenols are used as fungicides, herbicides, or insecticides. The fungicidal, herbicidal, or insecticidal properties depend on minor differences in the chemical structures of the different dinitrophenol compounds. Several dinitrophenol compounds have more than one pesticidal use. The pesticidal use of one dinitrophenol, dinoseb, was eliminated in the United States in 1986. There has recently been a voluntary cancellation of all US product registrations for the fungicide/miticide Dinocap. 

DNP was formerly used as a weight-reducing agent. 2,5-DNP is used in the manufacture of dyes, organic chemicals, and as a pH indicator. 2,4-DNP is used as an insecticide, acaricide, and fungicide. Dinitrophenols are also used in the manufacture of acaricides, herbicides, fungicides, and in the manufacture of styrene as inhibitors in the purification stills to reduce polymerization (Merck 1989 Coulter et al. 1969 HSDB 1994 Metcalf 1966 Sax and Lewis 1987). 

Other nitrogenous herbicides are derived from phenols and show the same UV spectrum shape as nitrophenol, such as dinoterb (terbutyl dinitrophenol, Fig. 57), for instance. 

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