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Book Review Pesticide Chemistry. (Series Studies in Environmental Science Vol. 32). Edited by Gy. Matolcsy M. Ndasy and V

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grouped together from a different viewpoint (keyword:
model enzymes). Beginning with the chemistry of the cyclodextrins, the discussion is concerned mainly with the
bonding of neutral guest molecules in host systems such as
cyclophanes and cryptophanes, though some ionic guest
molecules are also discussed. Chapter 4 ends with an account
of the host-guest chemistry of non-macrocyclic molecular
pincers.
Chapters 5 and 6 are devoted to inclusion complexes in the
solid state and their applications. Chapter 7 describes systems that can function as molecular switches, beginning with
those based on azobenzenes. Chapter 8 gives a very detailed
treatment of liquid crystal systems, from the physico-chemical fundamentals through LCDs to the latest applications in
polymer chemistry. The book concludes with short chapters
on surface-active agents, micelles and vesicles (Chapter 9),
organic conductors (Chapter lo), molecular electronics
(Chapter 1 l), and light-induced decomposition of water
(Chapter 12); these describe new developments, mainly
those based on supramolecular chemistry.
The division of such a new field as supramolecular chemistry into separate sub-areas is very difficult, and the author
addresses this problem in the preface. Thus, for example, the
photoactive cryptands (Chapter 2, Section 2.2.2.6) seem
rather out of place in the section on multinuclear host-guest
complexes (2.2.2), as also do the catenanes (Section 2.5) in
Chapter 2, which is on host-guest chemistry involving
cations and anions.
Excellent and detailed descriptions of synthetic methods
are given for some host molecules and supramolecuIar structures, e.g. Collet’s synthesis for cryptophanes, Corey’s total
synthesis of enterobactin, Schill‘s method for catenanes, and
Sauvage’s for catenands. Unfortunately the policy of making
each chapter self-contained results in some repetition, e.g.
the separation of the enantiomers of cyclotriveratrylene
derivatives appears on pages 173 and 217.
Last but not least, thanks to the 48 pages of literature
references (up to 1988) the book provides a good guide to
published work in many different areas of supramolecular
chemistry, especially in the author’s own fields of research.
However, the provision of references varies greatly between
individual topics. In Section 2.2 the introduction alone has
94 references, whereas there is only one reference for the
whole of Chapter 6. The collecting together of all the references at the end of the book is a good feature. However, it
does not entirely eliminate repeated searching, since in each
chapter the references begin again with [I].
Whereas most of the sections are written in such a way
that a knowledge at undergraduate level is enough to understand them, Section 2.3 goes into great depth, and Table 1
contains many abbreviations which are incomprehensible
without a familiarity with the original literature. The book
contains few spelling mistakes, although there are some
which occur repeatedly (e.g. Allcook instead of Allcock). On
page 191 the impression is given that Whitlock did not begin
his researches until after 1985. The modern German names
Benzen and Toluen are used; on the other hand, the pressure
unit atm (atmosphere) still finds its way into this book
(p. 271). The structural diagrams are clear and consistent,
which is a considerable achievement in view of the fact that
some of the three-dimensional structures are very complicated.
It has, of course, not been possible to include in this book
all that is known about supramolecular chemistry. For example, a few readers may notice the absence of some particularly effective host structures such as molecular boxes, collars o r belts. Syntheses also could have been given a further
324
33 VCH Verlaggesellschaft mbH, 0-6940 Weinheim, 1990
section, as the “dilution principle” and the “template effect”
have received insufficient attention. The coverage of historical aspects could also have been extended: the first macrocyclic polyethers were reported by Liittringhaus 30 years earlier than Pedersen, and even the chemistry of the cyclam
macrocycles has been known for many years.
Reactions, including those of a catalytic nature, that can
be carried out using supramolecular systems are treated
rather too briefly. Perhaps it will be possible in a future
edition to devote a separate chapter to these applications.
The desirability of publishing an English translation of the
work has already been mentioned at the 1989 Conference on
Macrocyclic Chemistry.
In summary, this is a very interesting book on the many
different aspects of supramolecular chemistry, which provides both a good introduction to the topic, through the
comprehensive introductory sections included in each of the
chapters, and a good starting point for reading the original
literature (with 48 pages of references). It is also a valuable
source of new ideas, especially in the last few chapters. However, two facts in particular stand out: the book is written in
the German language, and each page costs less than ten pfennigs!
Ulrich Liining [NB 1009 IE]
Institut fur Organische Chemie und Biochemie
der Universitat Freiburg (FRG)
Pesticide Chemistry. (Series: Studies in Environmental Science, Vol. 32). Edited by Cy. Mutolcsy, M . Nadasy and
I.: Andrisku. Elsevier, Amsterdam 1988. 800 pp., hardcover, HF1 495.00. - ISBN 0-444-98903-X
The last comprehensive review of the chemistry of plant
protection chemicals appeared about ten years ago. On the
other hand there are numerous excellent and up-to-date
monographs on individual topics which have been well cataloged. It is to be welcomed, therefore, that Gy. Matolcsy, M .
Nadusy and V: Andriska, as they indicate in the preface to
this new review of the field, have set out to devote particular
attention to the most recent developments in plant protection chemistry, and on products which exemplify interesting
new trends. The expert will immediately think in this context
of keywords such as pyrethroids, azoles, sterol biosynthesis
inhibitors, sulfonylureas, imidazolinones, ALS inhibitors,
chlorotics and photosynthesis inhibitors, and will be glad to
learn that at last a compact treatment of these topics, which
has long been needed, has arrived. However, the expectation
will be dampened to some extent on glancing through the
contents list of this bulky volume. The reader will find only
nine pages on pyrethroids, as a sub-section in a chapter on
“Insecticides of Natural Origin”, whereas a little later on, no
less than 43 pages are allocated to the older chlorinated
hydrocarbons. The triazoles, which are now probably the
most important and intensively studied single class of fungicides, are dealt with in eight pages, and the sulfonylureas,
which have set new standards in the area of herbicides, are
given only three pages. This apparent lack of topical emphasis can perhaps be explained by the book having been a long
time in preparation. From an analysis of the literature citations, which are very numerous in all the chapters, one can
conclude that the manuscript deadline was in 1984. The delay in publication is regrettable, expecially as the authors
have been exceptionally thorough and careful in summarizing the published material up to that date; the coverage is
considerably wider than in the earlier reviews, especially as
regards mechanisms of action, metabolism and the effects of
0570-0833/90j0303-0324$02.50/0
Angew. Chem. Int. Ed. Engl. 29 (1990) No. 3
residues, aspects which have been given more space for every
class of compounds where the information was available.
Within each of the six large chapters on insecticides, acaricides, nematicides, rodenticides, fungicides and herbicides,
the material is arranged strictly according to chemical classes. Of course this is reasonable, but it makes it more difficult
to recognize the characteristic behaviour of each of the various classes of compounds, which in practical use as well as
in research are determined by their common mechanisms of
action or activity spectra. The clarity of presentation within
the individual chapters would have benefited greatly from a
consistent and more visibly obvious division into the recurring sections dealing with chemistry, spectrum of biological
activity, mechanism of action, metabolism and toxicology,
together with a greater use of tables to summarize the information.
The chapter on insecticides is clearly dominated by the
conventional classes of compounds. The pyrethroids, for example, are definitely under-represented. Compared with the
space devoted to other compound classes one notices the
absence here not only of some of the newer products such as
Cyfluthrin and Fenpropathrin, but, more importantly, of
any impression of the considerable chemical research activity
in this field that was already under way in the late 1970s. For
example, although there is a description of one of the enantiospecific, but commercially quite insignificant, syntheses of
chrysanthemum dicarboxylic acid, one searches in vain for
one of the more commercially important permethrin acid
syntheses, which was the subject of a brilliant research
project. Again under phosphoric acid esters some important,
and even quite old, products such as Azodrina, (Monocrotophos), Counter" (Terbufos), MiraF (Isazofos) and
Nemacur" (Fenamifos) are not included. The last two are
also missing from the appropriate part of the chapter on
nema ticides.
In contrast the section on insect growth regulators is excellent. On the basis of the literature up to 1984, the theoretical
studies that have been carried out in this area with the aim
of developing highly specific insecticides with favorable toxicological properties are reviewed. The chemistry and synthesis of these compounds and the insect physiological aspects are discussed in detail. Research along these lines has
so far failed to yield products of wide applicability, despite
some limited successes in narrow areas, and the accurate
assessment given here still remains appropriate now.
On the other hand, the chapter of acaricides, the section
on triazoles, and some parts of the chapter on herbicides are
considerably diminished in value by the rapid further developments in these areas during the long time that it has taken
to complete the book. For example, it has not been possible
to include the new standards in acaricides that were introduced into the market between 1983 and 1985, namely
Hexythiazox (Nissorun"), and Clofentezine (ApolloS), nor
to convey an impression of the wide-ranging developments
and many new products in the triazoles area. The mechanism
whereby these act as sterol biosynthesis inhibitors is only
briefly mentioned as a literature reference.
However, the chapter on herbicides, which is the longest in
the book (300pp.), is a very detailed and comprehensive
account of these classes of compounds. Particularly noteworthy are the sections on phenoxyalkanecarboxylic acids,
phenoxyethanols and dinitroanilines. The chapter includes a
detailed review of structure-activity relationships and of the
biodecomposition of phenoxyacetic acids, a discussion of the
TCDD problem, and a comprehensive account of the research on 2,4-dichlorophenoxyethanol (DCPE) and on Buvinolg (pp. 533-541). Here, as also in many other parts of
Angm
Chem. In!. Ed. EngI. 29 (1990) No. 3
the book, one gains an interesting impression of plant protection research in Eastern Europe and of the products developed from it; this does not emerge to the same extent from
books published in the West. The photochemical decomposition of Trifluralin is described in detail, and alternative
routes are given in the two schemes on pages 608 and 609;
however, the difference between these is only one of emphasis, and this illustrates that there are many points where the
material could be tightened up and presented more concisely. In the case of the sulfonylureas there is regrettably no
mention of the results published in 1984 on the mechanism
of action of this group of compounds as acetolactate-synthase inhibitors, nor of the intensive worldwide chemical
research, leading to a flood of patents, that has occurred since
the appearance of the first examples of these compounds.
From today's standpoint the book definitely does not justify the claim to present current trends and synthetic methods of modern plant protection chemistry; furthermore,
some of the obsolete plant protection chemicals that are
discussed in detail here, such as the organomercury fungicides and the chlorinated hydrocarbon insecticides, need to
be differently evaluated nowadays. NevertheIess, despite the
fact that other more up-to-date books exist, the considerable
amount of material which this book contains, and the special
attention that is given to biochemical, toxicological and ecological aspects, make it a valuable addition to the existing
review literature. It will therefore be a useful source book for
those engaged in research or applications who need rapid
access to comprehensive information, and a guide to the
original pubhations on particular classes of compounds
that are or have been important in plant protection. The high
price means that it will not be easy for individuals to commit
themselves to buying it, but the book will find a place in
well-equipped departmental libraries.
Joachim Wei$miiller [NB 999 IE]
Bayer AG, Agrochemical Division
PF-Zentrum Monheim (FRG)
Modern Supercritical Fluid Chromatography. Edited by
C. M . White. Dr. Alfred Huthig Verlag, Heidelberg 1988.
xii, 239 pp., hardcover, DM 98.00. - ISBN 3-7785-1 569-1
Supercritical fluid chromatography (SFC), in which a supercritical gas is used as the mobile phase, has established a
place as a third technique intermediate between gas chromatography and liquid chromatography. Rapid strides are
being made in the development of this method and of commercially available instruments. In the book reviewed here
Curt M . White provides an up-to-date account of the development of SFC.
The editor has been successful in enlisting a number of
eminent authors as collaborators. The eleven chapters, dealing with such varied and topical themes as an introduction to
the mechanisms producing gradients in SFC, the advantages
and disadvantages of packed columns in SFC, the solubility
of modifiers in CO,, interfacing SFC to mass spectrometry
and FTIR, applications of SFC in petrochemicals analysis,
and restrictor properties, are all written by scientists with
many years of experience in these fields.
The individual contributions are self-contained rather
than forming a sequence of interdependent chapters. A few
of the authors preface their contributions by short introductions to the essentials of SFC, but the inclusion of a general
introductory overview would have given the book a better
defined structure, and would undoubtedly have made it useful to a wider readership.
i.; VCH ~ r l a g g r . s e l l , ~ ~ hmhH,
u / 1 D-6940 Weinheini, 1990
0570-0H233/90/0303-0325SC 02.Sf):fI
325
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