Characterization of 4-hydroxyphenylpyruvate dioxygenases, inhibition by herbicides and engineering for herbicide tolerance in crops

Hawkes, Timothy R.; Langford, Michael P.; Viner, Russell; Blain, Rachael E.; Callaghan, Fiona M.; Mackay, Elaine A.; Hogg, Bridget; Singh, Sanchita; Dale, Richard P.

doi:10.1016/j.pestbp.2019.01.006

Cited by 32 publications

(53 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In plants, HPPD inhibitors competitively restrain HPPA from chelating to Fe II . The production of plastoquinone is inhibited and phytoene is accumulated when the transformation of HPPA to HGA is interfered with an HPPD inhibitor [9,10]; consequently, plants become severely damage when exposed to sunlight, ultimately resulting in bleaching symptoms followed by necrosis and death [11,12]. Therefore, HPPD inhibitors play important roles in the herbicide industry.…”

Section: Introductionmentioning

confidence: 99%

“…A considerable number of HPPD inhibiting herbicides have recently been commercialized and applied in the agrochemical industry. These herbicides are mainly divided into three categories: triketones, pyrazoles, and isoxazoles [9,15,16]. Figure 1 shows some HPPD-inhibiting herbicides, namely mesotrione, tefuryltrione, isoxaflutole, topramezone, and pyrasulfotole.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Wang¹,

Huang²,

Shu³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

A series of aryloxyacetic acid derivatives were designed and synthesized as 4-hydoxyphenylpyruvate dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (K i = 0.011 µM) and I23 (K i = 0.012 µM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (K i = 0.013 µM). Furthermore, the newly synthesized compounds show significant greenhouse herbicidal activities against tested weeds at dosages of 150 g ai/ha. In particular, II4 exhibited high herbicidal activity for pre-emergence treatment that was slightly better than that of mesotrione. In addition, compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Wang¹,

Huang²,

Shu³

et al. 2020

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…(iii) Conferring herbicide resistance. Many herbicides act by inhibiting essential metabolic enzymes, and mutations that alleviate this inhibition confer resistance [56,57]. Continuous directed evolution has already been used to evolve antibiotic resistance in microbial enzymes [26,27]; this approach could be similarly applied to evolve herbicide-resistant crop enzymes.…”

Section: Future Perspectivesmentioning

confidence: 99%

Potential For Applying Continuous Directed Evolution To Plant Enzymes

García‐García

Joshi

Patterson

et al. 2020

Preprint

View full text Add to dashboard Cite

SUMMARYPlant evolution has produced enzymes that may not be optimal for maximizing yield and quality in today’s agricultural environments and plant biotechnology applications. By improving enzyme performance, it should be possible to alleviate constraints on yield and quality currently imposed by kinetic properties or enzyme instability. Enzymes can be optimized faster than naturally possible by applying directed evolution, which entails mutating a target gene in vitro and screening or selecting the mutated gene products for the desired characteristics. Continuous directed evolution is a more efficient and scalable version that accomplishes the mutagenesis and selection steps simultaneously in vivo via error-prone replication of the target gene and coupling of the host cell’s growth rate to the target gene’s function. However, published continuous systems require custom plasmid assembly, and convenient multipurpose platforms are not available. We discuss two systems suitable for continuous directed evolution of enzymes, OrthoRep in Saccharomyces cerevisiae and EvolvR in Escherichia coli, and our pilot efforts to adapt each system for high-throughput plant enzyme engineering. To test our modified systems, we used the thiamin synthesis enzyme THI4, previously identified as a prime candidate for improvement. Our adapted OrthoRep system shows promise for efficient plant enzyme engineering.

show abstract

“…When HPPD is inhibited, the levels of tocopherol and PQ decrease, leading to carotenoid depletion, then leaf bleaching and plant death . Many HPPD‐inhibiting herbicides are now introduced globally for use in the naturally tolerant major grain crops corn ( Zea mays ), rice ( Oryza sativa ) and wheat ( Triticum aestivum ), and in genetically modified (GM) soybean ( Glycine max ) …”

Section: Introductionmentioning

confidence: 99%

“…5,8 Many HPPD-inhibiting herbicides are now introduced globally for use in the naturally tolerant major grain crops corn (Zea mays), rice (Oryza sativa) and wheat (Triticum aestivum), and in genetically modified (GM) soybean (Glycine max). 9 Resistance to HPPD-inhibiting herbicides has thus far only been reported in North America in waterhemp (Amaranthus tuberculatus) and Palmer amaranth (Amaranthus palmeri). 3,10-16 Among these resistant populations, most of them have been selected by HPPD-inhibiting herbicides, with the exception of a Palmer amaranth population.…”

Section: Introductionmentioning

confidence: 99%

Evolution of resistance to HPPD‐inhibiting herbicides in a wild radish population via enhanced herbicide metabolism

Han

et al. 2020

Pest Management Science

View full text Add to dashboard Cite

BACKGROUND Relatively new herbicides that target 4‐hydroxyphenylpyruvate dioxygenase (HPPD) are now available for use on the world's great grain crops (rice, wheat, corn and soybean) and for other uses. With widespread and persistent use of HPPD‐inhibiting herbicides, the evolution of HPPD‐inhibiting herbicide resistant weeds is inevitable. Currently, resistance to HPPD‐inhibiting herbicides is known in two weed species, waterhemp and Palmer amaranth. Here, we report a HPPD‐inhibiting herbicide resistant wild radish population from the Western Australia grain belt. This population was not selected with HPPD‐inhibiting herbicides, rather it evolved resistance to earlier used herbicides with different modes of action and exhibits cross‐resistance to HPPD‐inhibiting herbicides. RESULTS Dose–response experiments showed the resistant (R) population exhibits 4 to 6.5‐fold resistance to the HPPD‐inhibiting herbicides mesotrione, tembotrione and isoxaflutole, compared to the susceptible (S) population. This resistance is not target‐site based as cloning of full coding sequences of the HPPD genes from S and R plants did not reveal resistance‐endowing single nucleotide polymorphisms. The HPPD gene expression levels are similar in S and R plants. In addition, no differences in [14C]‐mesotrione uptake and translocation were observed in the S and R plants. However, the time required for R plants to metabolise 50% [14C]‐mesotrione is 7.7‐fold faster than for the S plants. CONCLUSION We confirm resistance to HPPD‐inhibiting herbicides exists in a population of the economically damaging global weed wild radish. The resistance in this population is due to a non‐target‐site based enhanced rate of herbicide metabolism. © 2019 Society of Chemical Industry

show abstract

Characterization of 4-hydroxyphenylpyruvate dioxygenases, inhibition by herbicides and engineering for herbicide tolerance in crops

Cited by 32 publications

References 25 publications

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

Potential For Applying Continuous Directed Evolution To Plant Enzymes

Evolution of resistance to HPPD‐inhibiting herbicides in a wild radish population via enhanced herbicide metabolism

Contact Info

Product

Resources

About