Enhanced production of water‐soluble cinmethylin metabolites by Lolium rigidum populations with reduced cinmethylin sensitivity

Abstract Background Cinmethylin, a pre‐emergence herbicide inhibiting fatty acid thioesterase activity, has recently been introduced to Australian cereal cropping for the control of Lolium rigidum Gaud. (annual ryegrass). To date, there have been no confirmed cases of cinmethylin resistance identified in this species, but some populations exhibit reduced sensitivity to this herbicide. To explore the mechanism which contributes to reduced sensitivity of annual ryegrass to cinmethylin, the extent and nature of cinmethylin metabolism, using carbon‐14 (14C)‐labelled herbicide, were analysed in three reduced‐sensitivity annual ryegrass populations, alongside a susceptible population and cinmethylin‐tolerant wheat as controls. Results All samples showed the same metabolite profile, with the extent of production of a specific water‐soluble metabolite being correlated to the level of herbicide sensitivity. Application of the cytochrome P450 inhibitor phorate caused a decrease in water‐soluble metabolite production as well as seedling growth in the presence of cinmethylin, indicating that reduced cinmethylin sensitivity in annual ryegrass could be wholly or partially due to oxidative modification of cinmethylin. Conclusion Because annual ryegrass has the potential to metabolize cinmethylin in the same way as wheat, careful stewardship is required to ensure the longevity of this herbicide. © 2022 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

[1]  H. Beckie,et al.  Herbicide resistance across the Australian continent. , 2021, Pest management science.

[2]  H. Beckie,et al.  Pyroxasulfone-Resistant Annual Ryegrass (Lolium rigidum) Has Enhanced Capacity for Glutathione Transferase-Mediated Pyroxasulfone Conjugation. , 2021, Journal of Agricultural and Food Chemistry.

[3]  B. Nidetzky,et al.  Selective β-Mono-Glycosylation of a C15-Hydroxylated Metabolite of the Agricultural Herbicide Cinmethylin Using Leloir Glycosyltransferases , 2021, Journal of agricultural and food chemistry.

[4]  C. Preston,et al.  Resistance to Bixlozone and Clomazone in Cross-Resistant Rigid Ryegrass (Lolium rigidum) Populations from Southern Australia , 2021, Weed Science.

[5]  C. Preston,et al.  Review: evolutionary drivers of agricultural adaptation in Lolium spp. , 2020, Pest management science.

[6]  N. Navrot,et al.  Innate promiscuity of the CYP706 family of P450 enzymes provides a suitable context for the evolution of dinitroaniline resistance in weed. , 2020, The New phytologist.

[7]  S. Iwakami,et al.  Cytochrome P450-mediated herbicide metabolism in plants: Current understanding and prospects. , 2020, Pest management science.

[8]  H. Beckie,et al.  Cinmethylin controls multiple herbicide-resistant Lolium rigidum and its wheat selectivity is P450-based. , 2020, Pest management science.

[9]  C. Preston,et al.  Control of thiocarbamate-resistant rigid ryegrass (Lolium rigidum) in wheat in southern Australia , 2019, Weed Technology.

[10]  Steven L Levine,et al.  Review and recommendations on criteria to evaluate the relevance of pesticide interaction data for ecological risk assessments. , 2018, Chemosphere.

[11]  S. Powles,et al.  Enhanced Trifluralin Metabolism Can Confer Resistance in Lolium rigidum. , 2018, Journal of agricultural and food chemistry.

[12]  C. Preston,et al.  Resistance to Multiple PRE Herbicides in a Field-Evolved Rigid Ryegrass (Lolium rigidum) Population , 2018, Weed Science.

[13]  W. E. Dyer Stress-induced evolution of herbicide resistance and related pleiotropic effects. , 2018, Pest management science.

[14]  Johannes Hutzler,et al.  A new herbicidal site of action: Cinmethylin binds to acyl-ACP thioesterase and inhibits plant fatty acid biosynthesis. , 2018, Pesticide biochemistry and physiology.

[15]  S. Powles,et al.  Phorate can reverse P450 metabolism-based herbicide resistance in Lolium rigidum. , 2017, Pest management science.

[16]  Florent Baty,et al.  Dose-Response Analysis Using R , 2015, PLoS ONE.

[17]  Stephen B. Powles,et al.  Multiple herbicide‐resistant Lolium rigidum (annual ryegrass) now dominates across the Western Australian grain belt , 2014 .

[18]  S. Powles,et al.  Inheritance of evolved resistance to a novel herbicide (pyroxasulfone). , 2014, Plant science : an international journal of experimental plant biology.

[19]  Stephen B. Powles,et al.  Understanding the potential for resistance evolution to the new herbicide pyroxasulfone: Field selection at high doses versus recurrent selection at low doses , 2012 .

[20]  K. Kawai,et al.  Action mechanism of a novel herbicide, pyroxasulfone , 2009 .

[21]  Joshua S. Yuan,et al.  Non-target-site herbicide resistance: a family business. , 2007, Trends in plant science.

[22]  M. Barrett,et al.  Studies of clomazone mode of action , 2006 .

[23]  S. Powles,et al.  Recurrent selection with reduced herbicide rates results in the rapid evolution of herbicide resistance in Lolium rigidum , 2005, Theoretical and Applied Genetics.

[24]  M. Barrett,et al.  The basis for the safening of clomazone by phorate insecticide in cotton and inhibitors of cytochrome P450s , 2005 .

[25]  Julian J. Faraway,et al.  Practical Regression and Anova using R , 2002 .

[26]  S. Moss Detecting herbicide resistance: guidelines for conducting diagnostic tests and interpreting results. June 1999 , 1999 .

[27]  W. E. Dyer,et al.  Triallate Resistance inAvena fatuaL. Is Due to Reduced Herbicide Activation , 1996 .

[28]  J. Holtum,et al.  Dintroaniline Herbicide Resistance in Rigid Ryegrass (Lolium rigidum) , 1995, Weed Science.

[29]  A. Yang,et al.  Study of root uptake and xylem translocation of cinmethylin and related compounds in detopped soybean roots using a pressure chamber technique. , 1990, Plant physiology.

[30]  J. Weber,et al.  Influence of Simulated Rainfall and Soil Moisture on Herbicidal Activity of Cinmethylin , 1990, Weed Science.

[31]  P. Cornelius,et al.  Analyzing Herbicide Interactions: A Statistical Treatment of Colby's Method , 1988, Weed Technology.

[32]  E. Fuerst,et al.  Understanding the Mode of Action of the Chloroacetamide and Thiocarbamate Herbicides , 1987, Weed Technology.

[33]  Philip W. Lee,et al.  Metabolic fate of cinmethylin in goat , 1986 .