Polymeric Herbicides

The influences of herbicides on cell division fall into two classes, ie, dismption of the mitotic sequence and inhibition of mitotic entry from interphase (G, S, G2). If ceU-cycle analyses indicate increases in abnormal mitotic figures, combined with decreases in one or more of the normal mitotic stages, the effect is upon mitosis. Mitotic effects usually involve the microtubules of the spindle apparatus in the form of spindle depolymerization, blocked tubulin synthesis, or inhibited microtubule polymerization (163). Alkaloids such as colchicine [64-86-8J,viahla.stiae [865-21-4] and vincristine [57-22-7] dismpt microtubule function (164). Colchicine prevents microtubule formation and promotes disassembly of those already present. Vinblastine and vincristine also bind to free tubulin molecules, precipitating crystalline tubulin in the cytoplasm. The capacities of these dmgs to interfere with mitotic spindles, blocking cell division, makes them useful in cancer treatment. 

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. 

The majority of 2-methylphenol is used in the production of novolak phenoHc resins. High purity novolaks based on 2-methylphenol are used in photoresist appHcations (37). Novolaks based on 2-methylphenol are also epoxidized with epichlorohydrin, yielding epoxy resins after dehydrohalogenation, which are used as encapsulating resins in the electronics industry. Other uses of 2-methylphenol include its conversion to a dinitro compound, 4,6-dinitro-2-methylphenol [534-52-1] (DNOC), which is used as a herbicide (38). DNOC is also used to a limited extent as a polymerization inhibitor in the production of styrene, but this use is expected to decline because of concerns about the toxicity of the dinitro derivative. 

B. M., Price, M. W., and Stoner, W. C., Jr., Polymeric-pellet delivery systems for controlled release of aquatic herbicides, Toronto Controlled Release Society, Proc. 14th Int. Symp. Control. Rel. Bioact. Materials, 291-292, 1987. 

Ferrer and Barcelo [131] used online solid-phase-liquid chromatography mass spectrometry for the simultanous determination of organotin antifouling herbicides in marine water. The solid-phase extraction was carried out on polymeric cartridges after percolation of 100 ml of the seawater sample, and... 

Used in the manufacture of pesticides, herbicides, veterinary medicines, polymerization initiators, blowing agents, and other chemicals. 

Chlorophenols, manufacture of, 23 654 Chlorophenoxy acid herbicides, 73 304 (E) -(RS) -1 -(4-Chlorophenyl) -4,4-dimethyl-2-(lH- l,2,4-triazol-l-yl)-pent-l-en-3-ol, 73 47—48. See also 4-Chlorophenyl-4,4- dimethyltriazol pentenol 4-Chlorophenyl-4,4-dimethyltriazol pentenol, 73 40t, 47 48 Chlorophosphazenes, 19 55, 56 in silicone polymerization, 22 556... 

A potential polymeric herbicide and/or pesticide has been made from poly(vinyl alcohol) and 2,6-dichlorobenzaldehyde, which is a known pesticide with strong herbacidal and moderate fungicidal activity, as outlined in Equation 16. This polymer shows negligible hydrolysis at room temperature and only 2% hydrolysis after three days at 60°C. The extent of substitution ranged from 18-68% (56). 

In recent years there has been a growing interest in the use of polymeric herbicides, pesticides and drugs. Several reviews have appeared on this general area (69-71) and we earlier noted several examples of such potential behavior with poly(vinyl alcohol) modifications. These included modifications containing 6-methylthiopurine (an antileukemia drug) (55), 2,6-dichloro-benzaldehyde (a herbicide) (56), various enzymes (52,53), aspirin (analgesic)(51) and mercapto groups (46-49). 

Savage, K.E., C.L. McCormick, and B.H. Hutchinson, "Biological Evaluation of Polymeric Controlled Activity Herbicide Systems Containing Pendant Metribuzin,"... 

Fig. 5. Polymerization reactions that occur with the herbicide Propanil during biodegradation...

Uses Coolant and refrigerant herbicide and fumigant organic synthesis-methylating agent manufacturing of silicone polymers, pharmaceuticals, tetramethyl lead, synthetic rubber, methyl cellulose, agricultural chemicals and nonflammable films preparation of methylene chloride, carbon tetrachloride, chloroform low temperature solvent and extractant catalytic carrier for butyl rubber polymerization topical anesthetic fluid for thermometric and thermostatic equipment. 

Uses. Herbicide insecticide intermediate in the synthesis of fungicides polymerization inhibitor for vinyl aromatic compounds... 

Methyl chloride is used in the production of tetramethyllead antiknock compounds for gasoline and methyl silicone resins and polymers, and as a catalyst carrier in low-temperature polymerization (e g., butyl rubber), a refrigerant, a fluid for thermometric and thermostatic equipment, a methylating agent in organic synthesis, an extractant and low-temperature solvent, a herbicide, a topical antiseptic, and a slowing agent (lARC, 1986 Lewis, 1993). 

Several polymeric acyl-transfer reactants have been used to give am-ide/ester products in the solution phase. The excess polymer-bound acyl-transfer reactants and polymer-bound nucleofuge byproducts are easily removed after completion of the reactions. One such application involved the activated nitrophenyl esters 25 (reaction 8).40 A mixture of 10 acid chlorides was converted to an equimolar mixture of 10 amide products a potent preemergent herbicide was discovered using this parallel synthetic approach.41... 

Another nice example of nanostructuring an MIP layer is the work published by Wu et al. [138, 139] who developed a label-free optical sensor based on molecularly imprinted photonic polymers. Photonic crystals were prepared by self-assembly of silica nanospheres. The space between the spheres was then filled with MIP precursor solution. After polymerization, the silica was dissolved, leaving an MIP in the form of a 3D-ordered interconnected macroporous inverse polymer opal (Fig. 15). The authors were able to detect traces of the herbicide atrazine at low concentrations in aqueous solution [139]. Analyte adsorption into the binding sites resulted in a change in Bragg diffraction of the polymer characterized by a color modification (Fig. 15). 

Surugiu et al. [67] have introduced an Enzyme Immuno-Like Assays (EzILA) for the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D). The label was a 2,4-D conjugate with the tobacco peroxidase (TOP) enzyme, which allows for both colorimetric and chemiluminescent detection. In this case, the polymer imprinted with 2,4-D was synthesized in the form of microspheres. In contrast, despite its higher binding capacity for radiolabeled 2,4-D, a conventional MIP prepared by bulk polymerization showed only weak binding of the 2,4-D-TOP tracer. 

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