Boscalid is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases. It was first marketed by BASF in 2002 using their brand name Endura.[3] The compound is an biphenylamide derived inhibitor of succinate dehydrogenase.[4]
Inhibition of succinate dehydrogenase, the complex II in the mitochondrial respiration chain, has been known as a fungicidal mechanism of action since the first examples were marketed in the 1960s. The first compound in this class was carboxin, which had a narrow spectrum of useful biological activity, mainly on basidiomycetes and was used as a seed treatment. Many companies made analogues with the aim of expanding the range of species controlled and boscalid was successful in doing so.[5][6]
Synthesisedit
The first synthesis of boscalid was disclosed in patents filed by BASF in 1995.[7][8][9]
The aminobiphenyl required for reaction with the acid chloride of 2-chloronicotinic acid is prepared in two steps. The first is a palladium-catalysed Suzuki reaction, followed by reduction. As the final product has been manufactured at the multi-tonne scale, considerable efforts have been made to optimise these reactions.[8][9]
The estimated annual use of boscalid in US agriculture is mapped by the US Geological Survey and shows that it is mainly applied to fruit crops, with a maximum use of over 600,000 pounds (270,000 kg) in 2016.[12] Global sales in 2014 were estimated at $390 million. The compound lacks full control of important cereal diseases, especially septoria leaf blotch Zymoseptoria tritici, which has limited its potential.[5]
Human safetyedit
Boscalid has low acute toxicity:[1] the Codex Alimentarius database maintained by the FAO lists the maximum residue limits for it in various food products.[13]
Environmental effectsedit
The compound is very persistent in field conditions[1] and its environmental fate and consequent ecotoxicology have been reviewed.[4]
Resistance managementedit
Fungal populations have the ability to develop resistance to SDHI inhibitors.[14] This potential can be mitigated by careful management. Reports of individual pest species becoming resistant[1] are monitored by manufacturers, regulatory bodies such as the EPA and the Fungicides Resistance Action Committee (FRAC).[15] The risks of resistance developing can be reduced by using a mixture of two or more fungicides which each have activity on relevant pests but with unrelated mechanisms of action. FRAC assigns fungicides into classes so as to facilitate this.[16]
Brandsedit
Boscalid is the ISOcommon name for the active ingredient which is formulated into the branded product sold to end-users. It was also known as nicobifen.[17] Endura and Emerald are the brand names first used by BASF's formulations[3] but the compound has subsequently been sold under a range of product names.[1]
Referencesedit
^ abcdePesticide Properties Database (2023-07-25). "Boscalid". University of Hertfordshire. Retrieved 2023-08-10.
^ abYibing, He (2006). "Boscalid" (PDF). FAO. Retrieved 2023-08-10.
^ abcWalter, Harald (2016). "Fungicidal Succinate-Dehydrogenase-Inhibiting Carboxamides". In Lamberth, Clemens; Dinges, Jürgen (eds.). Bioactive Carboxylic Compound Classes: Pharmaceuticals and Agrochemicals. Wiley. pp. 405–425. doi:10.1002/9783527693931.ch31. ISBN9783527339471.
^"History of SDHI-fungicides". frac.info. Retrieved 2023-07-26.
^US patent 5589493, Eicken, K; Goetz, N & Harreus, A et al., "Anilide derivatives and their use for combating botrytis", published 1996-12-31, assigned to BASF SE
^ abGlasnov, Toma N.; Kappe, C. Oliver (2010). "Toward a Continuous-Flow Synthesis of Boscalid" (PDF). Advanced Synthesis & Catalysis. 352 (17): 3089–3097. doi:10.1002/adsc.201000646.
^ abTakale, Balaram S.; Thakore, Ruchita R.; Mallarapu, Rushil; Gallou, Fabrice; Lipshutz, Bruce H. (2020). "A Sustainable 1-Pot, 3-Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water". Organic Process Research & Development. 24: 101–105. doi:10.1021/acs.oprd.9b00455. S2CID 212964123.
^Oyedotun, Kayode S.; Lemire, Bernard D. (2004). "The Quaternary Structure of the Saccharomyces cerevisiae Succinate Dehydrogenase". Journal of Biological Chemistry. 279 (10): 9424–9431. doi:10.1074/jbc.M311876200. PMID 14672929.
^Avenot, Hervé F.; Michailides, Themis J. (2010). "Progress in understanding molecular mechanisms and evolution of resistance to succinate dehydrogenase inhibiting (SDHI) fungicides in phytopathogenic fungi". Crop Protection. 29 (7): 643–651. doi:10.1016/j.cropro.2010.02.019.
^US Geological Survey (2021-10-12). "Estimated Agricultural Use for boscalid, 2019". Retrieved 2023-08-10.
^Cosseboom, Scott; Hu, Mengjun (2021). "Identification and Characterization of Fungicide Resistance in Botrytis Populations from Small Fruit Fields in the Mid-Atlantic United States". Plant Disease. 105 (9): 2366–2373. doi:10.1094/pdis-03-20-0487-re. PMID 33719541. S2CID 232231834.
^"Search Fungicides to find FRAC Recommendations". Retrieved 2020-09-04.
^"Compendium of Pesticide Common Names: Boscalid". BCPC. Retrieved 2023-07-27.
External linksedit
PPDB pesticides properties database entry for boscalid
December 15, 2023
boscalid, broad, spectrum, fungicide, used, agriculture, protect, crops, from, fungal, diseases, first, marketed, basf, 2002, using, their, brand, name, endura, compound, biphenyl, amide, derived, inhibitor, succinate, dehydrogenase, namespreferred, iupac, nam. Boscalid is a broad spectrum fungicide used in agriculture to protect crops from fungal diseases It was first marketed by BASF in 2002 using their brand name Endura 3 The compound is an biphenyl amide derived inhibitor of succinate dehydrogenase 4 Boscalid NamesPreferred IUPAC name 2 chloro N 4 chloro 1 1 biphenyl 2 yl pyridine 3 carboxamideOther names BAS 510F NicobifenIdentifiersCAS Number 188425 85 6 Y3D model JSmol Interactive imageBeilstein Reference 10092464ChEBI CHEBI 81822 YChEMBL ChEMBL1076544 Y EMBL ChemSpider 184713 YDrugBank DB12792ECHA InfoCard 100 115 343EC Number 606 143 0KEGG C18547 YPubChem CID 213013UNII 32MS8ZRD1VCompTox Dashboard EPA DTXSID6034392InChI InChI 1S C18H12Cl2N2O c19 13 9 7 12 8 10 13 14 4 1 2 6 16 14 22 18 23 15 5 3 11 21 17 15 20 h1 11H H 22 23 f h22H YKey WYEMLYFITZORAB UHFFFAOYSA N YSMILES C1 CC C C C1 C2 CC C C C2 Cl NC O C3 C N CC C3 ClProperties 1 Chemical formula C 18H 12Cl 2N 2OMolar mass 343 21Appearance White to beige coloured crystalline powderDensity 1 381 g cm3Melting point 143 CSolubility in water 4 6 mg L 20 C log P 2 96HazardsGHS labelling 2 PictogramsHazard statements H411Precautionary statements P273 P391 P501Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references Contents 1 History 2 Synthesis 3 Mechanism of action 4 Usage 5 Human safety 6 Environmental effects 7 Resistance management 8 Brands 9 References 10 External linksHistory editInhibition of succinate dehydrogenase the complex II in the mitochondrial respiration chain has been known as a fungicidal mechanism of action since the first examples were marketed in the 1960s The first compound in this class was carboxin which had a narrow spectrum of useful biological activity mainly on basidiomycetes and was used as a seed treatment Many companies made analogues with the aim of expanding the range of species controlled and boscalid was successful in doing so 5 6 Synthesis editThe first synthesis of boscalid was disclosed in patents filed by BASF in 1995 7 8 9 nbsp The aminobiphenyl required for reaction with the acid chloride of 2 chloronicotinic acid is prepared in two steps The first is a palladium catalysed Suzuki reaction followed by reduction As the final product has been manufactured at the multi tonne scale considerable efforts have been made to optimise these reactions 8 9 Mechanism of action editSuccinate dehydrogenase inhibitors SDHI of this type act by binding at the quinone reduction site of the enzyme complex preventing ubiquinone from doing so As a consequence the tricarboxylic acid cycle and electron transport chain cannot function 10 11 Usage editBoscalid has fungicidal effects against a wide range of crop pests These include Alternaria grey mold Botrytis cinerea white mold Sclerotinia sclerotiorum and powdery mildew Uncinula necator As a result it has use in crops including fruits soybeans and vegetables 3 5 nbsp Boscalid usage in the US to 2019 estimated The estimated annual use of boscalid in US agriculture is mapped by the US Geological Survey and shows that it is mainly applied to fruit crops with a maximum use of over 600 000 pounds 270 000 kg in 2016 12 Global sales in 2014 were estimated at 390 million The compound lacks full control of important cereal diseases especially septoria leaf blotch Zymoseptoria tritici which has limited its potential 5 Human safety editBoscalid has low acute toxicity 1 the Codex Alimentarius database maintained by the FAO lists the maximum residue limits for it in various food products 13 Environmental effects editThe compound is very persistent in field conditions 1 and its environmental fate and consequent ecotoxicology have been reviewed 4 Resistance management editFungal populations have the ability to develop resistance to SDHI inhibitors 14 This potential can be mitigated by careful management Reports of individual pest species becoming resistant 1 are monitored by manufacturers regulatory bodies such as the EPA and the Fungicides Resistance Action Committee FRAC 15 The risks of resistance developing can be reduced by using a mixture of two or more fungicides which each have activity on relevant pests but with unrelated mechanisms of action FRAC assigns fungicides into classes so as to facilitate this 16 Brands editBoscalid is the ISO common name for the active ingredient which is formulated into the branded product sold to end users It was also known as nicobifen 17 Endura and Emerald are the brand names first used by BASF s formulations 3 but the compound has subsequently been sold under a range of product names 1 References edit a b c d e Pesticide Properties Database 2023 07 25 Boscalid University of Hertfordshire Retrieved 2023 08 10 GHS Classification pubchem ncbi nlm nih gov 2023 07 22 Retrieved 2023 07 27 a b c Endura fungicide PDF EPA 2002 11 08 Retrieved 2023 08 10 a b Yibing He 2006 Boscalid PDF FAO Retrieved 2023 08 10 a b c Walter Harald 2016 Fungicidal Succinate Dehydrogenase Inhibiting Carboxamides In Lamberth Clemens Dinges Jurgen eds Bioactive Carboxylic Compound Classes Pharmaceuticals and Agrochemicals Wiley pp 405 425 doi 10 1002 9783527693931 ch31 ISBN 9783527339471 History of SDHI fungicides frac info Retrieved 2023 07 26 US patent 5589493 Eicken K Goetz N amp Harreus A et al Anilide derivatives and their use for combating botrytis published 1996 12 31 assigned to BASF SE a b Glasnov Toma N Kappe C Oliver 2010 Toward a Continuous Flow Synthesis of Boscalid PDF Advanced Synthesis amp Catalysis 352 17 3089 3097 doi 10 1002 adsc 201000646 a b Takale Balaram S Thakore Ruchita R Mallarapu Rushil Gallou Fabrice Lipshutz Bruce H 2020 A Sustainable 1 Pot 3 Step Synthesis of Boscalid Using Part per Million Level Pd Catalysis in Water Organic Process Research amp Development 24 101 105 doi 10 1021 acs oprd 9b00455 S2CID 212964123 Oyedotun Kayode S Lemire Bernard D 2004 The Quaternary Structure of the Saccharomyces cerevisiae Succinate Dehydrogenase Journal of Biological Chemistry 279 10 9424 9431 doi 10 1074 jbc M311876200 PMID 14672929 Avenot Herve F Michailides Themis J 2010 Progress in understanding molecular mechanisms and evolution of resistance to succinate dehydrogenase inhibiting SDHI fungicides in phytopathogenic fungi Crop Protection 29 7 643 651 doi 10 1016 j cropro 2010 02 019 US Geological Survey 2021 10 12 Estimated Agricultural Use for boscalid 2019 Retrieved 2023 08 10 FAO WHO Boscalid Cosseboom Scott Hu Mengjun 2021 Identification and Characterization of Fungicide Resistance in Botrytis Populations from Small Fruit Fields in the Mid Atlantic United States Plant Disease 105 9 2366 2373 doi 10 1094 pdis 03 20 0487 re PMID 33719541 S2CID 232231834 Fungicides Resistance Action Committee website Search Fungicides to find FRAC Recommendations Retrieved 2020 09 04 Compendium of Pesticide Common Names Boscalid BCPC Retrieved 2023 07 27 External links editPPDB pesticides properties database entry for boscalid Retrieved from https en wikipedia org w index php title Boscalid amp oldid 1174698863, wikipedia, wiki, book, books, library,
