The Discovery of Oxathiapiprolin: A New, Highly-Active Oomycete Fungicide with a Novel Site of Action

152

The agrochemical industry is searching continuously for new pesticides to develop products that have optimal efficacy, lower application rates in the field, increased selectivity, favourable toxicological and environmental safety, enhanced user friendliness and better economic viability. One strategy by which to achieve these ambitious goals makes use of the unique properties of molecules containing asymmetric centres. In the past, many natural products and their congeners have been a source of inspiration in the design of new active ingredients, and the molecular structures of the resulting compounds have become increasingly complex; some 30% contain fragments with asymmetric centres. However, despite enormous progress in catalytic asymmetric processes over the past decade, few agrochemicals are produced in an enantiomerically pure or enriched form on an industrial scale. Since 2007, ∼ 43% of the 44 products launched (insecticides, acaricides, fungicides, nematicides and herbicides) contain one or more asymmetric centres in the molecule (∼ 47%) and most have been launched as racemic mixtures of enantiomers or diastereomers. This review provides an overview of the current status of chiral agrochemicals launched over the past 10 years and describes the inherently connected challenges of modern agricultural chemistry by managing important aspects resulting from the stereochemistry of these innovative products. © 2018 Society of Chemical Industry.

Section: Selected Chiral Development Candidate Fungicidesmentioning

confidence: 95%

Section: Fungicidesmentioning

confidence: 99%

Section: Fungicidesmentioning

confidence: 99%

See 1 more Smart Citation

Current status of chirality in agrochemicals

Jeschke

2018

152

“…Oxathiapiprolin (Fig. ), is the first member of the halogenated piperidinyl thiazole fungicides, and contains a mixture of 5‐methyl‐3‐(trifluoromethyl)‐1 H ‐pyrazole, which has been selected as important for its xylem mobility, and 2,6‐difluoro‐phenyl moieties. It is highly active against plant diseases caused by Oomycete pathogens.…”

Section: Fungicidesmentioning

confidence: 99%

Latest generation of halogen‐containing pesticides

Jeschke

2017

200

134

Agriculture is confronted with enormous challenges, from production of enough high-quality food to water use, environmental impacts and issues combined with a continually growing world population. Modern agricultural chemistry has to support farmers by providing innovative agrichemicals, used in applied agriculture. In this context, the introduction of halogen atoms into an active ingredient is still an important tool to modulate the properties of new crop protection compounds. Since 2010, around 96% of the launched products (herbicides, fungicides, insecticides/acaricides and nematicides) contain halogen atoms. The launched nematicides contain the largest number of halogen atoms, followed by insecticides/acaricides, herbicides and fungicides. In this context, fungicides and herbicides contain in most cases fluorine atoms, whereas nematicides and insecticides contain in most cases 'mixed' halogen atoms, for example chlorine and fluorine. This review gives an overview of the latest generation of halogen-containing pesticides launched over the past 6 years and describes current halogen-containing development candidates. © 2017 Society of Chemical Industry.

“…Oxathiapiprolin ( 114 ) achieves a paradigm shift in the use rate of downy mildew and late blight fungicides as it works reliably at one‐tenth of the conventional application rates (Fig. S11) , …”

Section: Combined Approaches – True Masterpieces Of Scaffold Hoppingmentioning

confidence: 99%

Agrochemical lead optimization by scaffold hopping

Lamberth

2017

102

Scaffold hopping, the exchange of a specific portion of a potential active ingredient with another substructure with the aim of finding isofunctional molecular structures with significantly different molecular backbones, often offers the chance in lead discovery or optimization to mitigate problems related to toxicity, intellectual property, and insufficient potency or stability. Scaffold hopping tools such as isosteric ring replacement including 1,3 nitrogen shift and cyclic imine-amide isosterism, but also ring opening and ring closure approaches, functional group isosterism, reversion of functional groups, chain shortening, chain lengthening, and scaffolds delivered by natural products, have become a permanent fixture of the innovation and optimization process in crop protection research. Their appropriate use will be explained through examples of success stories in the field of agrochemistry. Analogies to, but also differences from, the main categories of scaffold hopping in medicinal drug discovery are discussed. © 2017 Society of Chemical Industry.