Discovery and SAR of Pinoxaden: A New Broad Spectrum, Postemergence Cereal Herbicide

Muehlebach, Michel; Brunner, H.; Cederbaum, Fredrik; Maetzke, Thomas; Mutti, R. J.; Schnyder, Anita; Stoller, André; Wendeborn, Sebastian; Wenger, Jean; Boutsalis, Peter; Cornes, Derek; Friedmann, Adrian; Glock, Jutta; Hofer, U.; Hole, Stephen; Niderman, Thierry; Quadranti, M.

doi:10.1002/9783527611249.ch10

Cited by 13 publications

(15 citation statements)

References 2 publications

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“…Biological evaluation of a number of analogues 15 led to a general structure–activity profile, summarised in a pictorial form (Fig. 6), from which the following key messages may be extracted 29. Within 4‐aryl‐pyrazolidine‐3,5‐diones, an optimal structural fragment combination associating a 2,6‐diethyl‐4‐methyl‐phenyl part to a [1,4,5]oxadiazepane ring generated pinoxaden dione 15a for high graminicidal activity and cereal crop tolerance to both wheat and barley.…”

Section: Resultsmentioning

confidence: 99%

“…14b ) the ring, were prepared by N , N ′‐alkylation of the bis‐anion of 1,2‐bis‐BOC protected hydrazine 11 with an appropriate bis‐mesylate reagent 12 , followed by BOC‐deprotection of 13 under standard conditions. The [1,4,5]oxadiazepane derivatives 14a / 14c 17 and the benzyloxy‐[1,2]diazepane analogue 14b were produced as hydrobromide salts, facilitating isolation and further handling.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…6), from which the following key messages may be extracted. 29 Within 4-aryl-pyrazolidine-3,5-diones, an optimal structural fragment combination associating a 2,6-diethyl-4-methyl-phenyl part to a [1,4,5]oxadiazepane ring generated pinoxaden dione 15a for high graminicidal activity and cereal crop tolerance to both wheat and barley. Each area contributed in a distinct and differentiated manner to overall bioperformance.…”

Section: Structure-activity Relationships Summarymentioning

confidence: 99%

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Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: Chemistry and biology of the cereal herbicide pinoxaden

Muehlebach

Cederbaum

Cornes

et al. 2011

Pest Management Science

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Methodsmentioning

confidence: 99%

Section: Structure-activity Relationships Summarymentioning

confidence: 99%

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Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: Chemistry and biology of the cereal herbicide pinoxaden

Muehlebach

Cederbaum

Cornes

et al. 2011

Pest Management Science

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“…and other monocotyledonous weed species in cereals. 70 Pinoxaden is hydrolysed very rapidly in soil or plants, forming the vinylogous 'pinoxaden acid' (R = H) under aerobic, aerobic-anaerobic and sterile-aerobic conditions as a herbicidally active metabolite (see also Section 7.3). 69 Its tolerance in key cereal crops (wheat, barley) under adverse climatic conditions is obtained by incorporating the proprietary safener (see Section 6) cloquintocet-mexyl into an easy-to-use liquid formulation, which delivers maximum performance of pinoxaden when used with a specially optimised adjuvant.…”

Section: Acetyl Coa Carboxylase (Accase) Inhibitorsmentioning

confidence: 99%

Progress of modern agricultural chemistry and future prospects

2015

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Agriculture is facing an enormous challenge: it must ensure that enough high-quality food is available to meet the needs of a continually growing population. Current and future agronomic production of food, feed, fuel and fibre requires innovative solutions for existing and future challenges, such as climate change, resistance to pests, increased regulatory demands, renewable raw materials or requirements resulting from food chain partnerships. Modern agricultural chemistry has to support farmers to manage these tasks. Today, the so-called 'side effects' of agrochemicals regarding yield and quality are gaining more importance. Agrochemical companies with a strong research and development focus will have the opportunity to shape the future of agriculture by delivering innovative integrated solutions. This review gives a comprehensive overview of the innovative products launched over the past 10 years and describes the progress of modern agricultural chemistry and its future prospects.

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“…), foxtails ( Setaria spp.) and other monocotyledonous weed species in cereals . It was found that pinoxaden is hydrolysed very rapidly in soil to ‘pinoxaden acid’ under aerobic, aerobic–anaerobic and sterile–aerobic conditions as herbicidally active metabolite (Fig.…”

Section: Proherbicides For Weed Controlmentioning

confidence: 99%

Propesticides and their use as agrochemicals

2015

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The synthesis of propesticides is an important concept in design of modern agrochemicals with optimal efficacy, environmental safety, user friendliness and economic variability. Based on increasing knowledge of the biochemistry and genetics of major pest insects, weeds and agricultural pathogens, the search for selectivity has become an ever more important part of pesticide development and can be achieved by appropriate structural modifications of the active ingredient. Propesticides affect the absorption, distribution, metabolism and excretion parameters, which can lead to biological superiority of these modified active ingredients over their non-derivatised analogues. Various selected commercial propesticides testify to the successful utilisation of this concept in the design of agrochemicals. This review describes comprehensively the successful utilisation of propesticides and their role in syntheses of modern agrochemicals, exemplified by selected commercial products coming from different agrochemical areas.

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Discovery and SAR of Pinoxaden: A New Broad Spectrum, Postemergence Cereal Herbicide

Cited by 13 publications

References 2 publications

Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: Chemistry and biology of the cereal herbicide pinoxaden

Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part 2: Chemistry and biology of the cereal herbicide pinoxaden

Progress of modern agricultural chemistry and future prospects

Propesticides and their use as agrochemicals

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