unique role of halogen substituents in the design of modern agrochemicals

The past 30 years have witnessed a period of significant expansion in the use of halogenated compounds in the field of agrochemical research and development. The introduction of halogens into active ingredients has become an important concept in the quest for a modern agrochemical with optimal effic...

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Bibliographic Details
Published in:Pest management science 2010, Vol.66 (1), p.10-27
Main Author: Jeschke, Peter
Format: Article
Language:English
Subjects:
Agriculture
agrochemicals
bioavailability
Biological and medical sciences
Chemical compounds
Chlorine
Control
Effects
Fundamental and applied biological sciences. Psychology
Fungal plant pathogens
fungicides
Fungicides, Industrial - chemistry
halogen effects
halogenated agrochemicals
halogens
Halogens - chemistry
herbicides
Herbicides - chemistry
insecticides
Insecticides - chemistry
literature reviews
mechanism of action
mode of action
Molecules
Parasitic plants. Weeds
Pesticides
physicochemical properties
physicochemistry
Phytopathology. Animal pests. Plant and forest protection
Protozoa. Invertebrates
R&D
Research & development
resistance
selectivity
structure-activity relationship
structure-activity relationships
Weeds
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Summary:The past 30 years have witnessed a period of significant expansion in the use of halogenated compounds in the field of agrochemical research and development. The introduction of halogens into active ingredients has become an important concept in the quest for a modern agrochemical with optimal efficacy, environmental safety, user friendliness and economic viability. Outstanding progress has been made, especially in synthetic methods for particular halogen-substituted key intermediates that were previously prohibitively expensive. Interestingly, there has been a rise in the number of commercial products containing 'mixed' halogens, e.g. one or more fluorine, chlorine, bromine or iodine atoms in addition to one or more further halogen atoms. Extrapolation of the current trend indicates that a definite growth is to be expected in fluorine-substituted agrochemicals throughout the twenty-first century. A number of these recently developed agrochemical candidates containing halogen substituents represent novel classes of chemical compounds with new modes of action. However, the complex structure-activity relationships associated with biologically active molecules mean that the introduction of halogens can lead to either an increase or a decrease in the efficacy of a compound, depending on its changed mode of action, physicochemical properties, target interaction or metabolic susceptibility and transformation. In spite of modern design concepts, it is still difficult to predict the sites in a molecule at which halogen substitution will result in optimal desired effects. This review describes comprehensively the successful utilisation of halogens and their unique role in the design of modern agrochemicals, exemplified by various commercial products from Bayer CropScience coming from different agrochemical areas.
ISSN:1526-498X
1526-4998
1526-4998
DOI:10.1002/ps.1829