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Strobilurin

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475: 371: 459: 491: 443: 291: 262: 347: 312: 225: 196: 175: 120: 52:. Commercial strobilurin fungicides were developed through optimization of photostability and activity. Strobilurins represented a major development in fungus-based fungicides. First released in 1996, there are now ten major strobilurin fungicides on the market, which account for 23-25 % of the global fungicide sales. Examples of commercialized strobilurin derivatives are 87:
Strobilurins are mostly contact fungicides with a long half time as they are absorbed into the cuticle and not transported any further. They have a suppressive effect on other fungi, reducing competition for
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Schramm, Georg; Steglich, Wolfgang; Anke, Timm; Oberwinkler, Franz (1978). "Antibiotika aus Basidiomyceten, III. Strobilurin a und B, antifungische Stoffwechselprodukte aus Strobilurus tenacellus".
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Juliet D. Tang, Tina Ciaramitaro, Maria Tomaso-Peterson, Susan V. Diehl (2017). "Activity of Two Strobilurin Fungicides Against Three Species of Decay Fungi in Agar Plate Tests".
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Zakharychev, Vladimir V; Kovalenko, Leonid V (1998-06-30). "Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors".
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The discovery of the strobilurin class of fungicides led to the development of a group of commercial fungicides used in agriculture. Examples are shown below.
909: 776: 670: 592: 566: 866:"Antibiotics from basidiomycetes. IX. Oudemansin, an antifungal antibiotic from Oudemansiella mucida (Schrader ex Fr.) hoehnel (Agaricales)" 237:. Its structure was originally incorrectly assigned and is now considered to be identical to that of strobilurin G, produced by 977: 972: 579:
Sauter, Hubert; Steglich, Wolfgang; Anke, Timm (1999). "Strobilurins: Evolution of a New Class of Active Substances".
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hydroxy group in place of the aromatic methoxy group of strobilurin H is called strobilurin F1 and is found in
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are a group of natural products and their synthetic analogs. A number of strobilurins are used in
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The oudemansins are closely related to the strobilurins and are also quinone outside inhibitors.
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The first parent natural products, strobilurins A and B, were extracted from the fungus
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10.1002/(SICI)1521-3773(19990517)38:10<1328::AID-ANIE1328>3.0.CO;2-1
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Anke, Timm; Hecht, Hans Jürgen; Chramm, Georgs; Steglich, Wolfgang (1979).
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Peter Jeschke, Matthias Witschel, Wolfgang Krämer, Ulrich Schirmer (eds.):
346: 311: 261: 224: 195: 174: 144:, and others. When first isolated it was incorrectly assigned as the E E E 119: 891: 332: 242: 89: 323: 695:"Basidiomycetes as a Source for New Bioactive Natural Products" 241:. A related material, hydroxystrobilurin D, with an additional 245:
group attached to the methyl of the main chain is produced by
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Schaefer, Bernd (2014). "Agrochemicals: 8.2 Strobilurins".
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Agricultural mycocides for the 21st century: strobilurins
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Anke, T.; Erkel, G. (2002). "Non-β-Lactam Antibiotics".
35:(Quinone outside Inhibitors), which act to inhibit the 406:. The latter fungus also produces oudemansin B, with R 126:
Strobilurin A (also known as mucidin) is produced by
693:Lorenzen, K.; Anke, T. (1998). Mori, Kenji (ed.). 911:Resistance to strobilurins in the southern USA 8: 628:: CS1 maint: multiple names: authors list ( 104:and preventing growth of the target fungi. 705:(4). Bentham Science Publishers: 329–364. 688: 686: 684: 682: 648: 646: 644: 946:, from: David Moore, Geoffrey D. Robson, 881: 655:Natural Products in the Chemical Industry 581:Angewandte Chemie International Edition 523: 438: 27:. They are part of the larger group of 754: 752: 750: 748: 746: 744: 742: 740: 738: 736: 621: 160:9-Methoxystrobilurin A is produced by 152:as being the E Z E isomer, as shown. 7: 14: 711:10.2174/1385272802666220128213627 561:, 3rd edition, Wiley-VCH, 2019, 559:Modern Crop Protection Compounds 489: 473: 457: 441: 369: 345: 310: 289: 260: 223: 194: 173: 118: 952:21st Century Guidebook to Fungi 938:from the original on 2019-09-08 918:from the original on 2019-09-08 835:10.1070/rc1998v067n06abeh000426 297:Strobilurin F2 is produced by 1: 353:Strobilurin X is produced by 322:. The natural product with a 318:Strobilurin H is produced by 268:Strobilurin E is produced by 231:Strobilurin D is produced by 202:Strobilurin C is produced by 181:Strobilurin B is produced by 148:but was later identified by 883:10.7164/antibiotics.32.1112 769:10.1007/978-3-662-10378-4_5 663:10.1007/978-3-642-54461-3_8 999: 870:The Journal of Antibiotics 414:= Cl. Oudemansin X, with R 271:Crepidotus fulvotomentosus 699:Current Organic Chemistry 809:Russian Chemical Reviews 616:Proc. IRG Annual Meeting 545:10.1002/cber.19781110806 422:= MeO was isolated from 761:Industrial Applications 978:Complex III inhibitors 432:Synthetic strobilurins 425:Oudemansiella radicata 156:9-Methoxystrobilurin A 135:Strobilurus tenacellus 49:Strobilurus tenacellus 948:Anthony P. J. Trinci 811:] (Успехи химии) 763:. pp. 101–104. 657:. pp. 688–704. 394:Oudemansiella mucida 248:Mycena sanguinolenta 234:Cyphellopsis anomala 129:Oudemansiella mucida 108:Natural strobilurins 827:1998RuCRv..67..535Z 404:Xerula melanotricha 218:Strobilurin D and G 973:Respiratory toxins 618:: IRG/WP 17-30704. 533:Chemische Berichte 876:(11): 1112–1117. 778:978-3-642-07481-3 672:978-3-642-54460-6 587:(10): 1328–1349. 567:978-3-527-34089-7 399:Mycena polygramma 94:electron transfer 37:respiratory chain 990: 945: 944: 943: 925: 924: 923: 896: 895: 885: 861: 855: 854: 802: 783: 782: 756: 731: 730: 690: 677: 676: 650: 639: 633: 627: 619: 611: 605: 604: 576: 570: 555: 549: 548: 539:(8): 2779–2784. 528: 493: 477: 461: 445: 373: 349: 314: 293: 264: 227: 198: 177: 146:geometric isomer 122: 39:at the level of 998: 997: 993: 992: 991: 989: 988: 987: 958: 957: 941: 939: 928: 921: 919: 908: 905: 900: 899: 863: 862: 858: 804: 803: 786: 779: 758: 757: 734: 692: 691: 680: 673: 652: 651: 642: 620: 613: 612: 608: 578: 577: 573: 556: 552: 530: 529: 525: 520: 512:Plant pathology 508: 501: 500: 494: 485: 484: 482:Kresoxim methyl 478: 469: 468: 466:Trifloxystrobin 462: 453: 452: 446: 434: 421: 417: 413: 409: 387: 383: 363: 342: 307: 286: 257: 220: 211:X. melanotricha 191: 170: 158: 150:total synthesis 115: 110: 92:; they inhibit 82:trifloxystrobin 58:kresoxim-methyl 32: 12: 11: 5: 996: 994: 986: 985: 980: 975: 970: 960: 959: 956: 955: 954:, 2nd edition. 926: 904: 903:External links 901: 898: 897: 856: 819:IOP Publishing 784: 777: 732: 678: 671: 640: 606: 571: 550: 522: 521: 519: 516: 515: 514: 507: 504: 503: 502: 498:Pyraclostrobin 496: 495: 488: 486: 480: 479: 472: 470: 464: 463: 456: 454: 448: 447: 440: 433: 430: 419: 415: 411: 407: 385: 381: 375: 374: 362: 359: 351: 350: 341: 338: 316: 315: 306: 303: 295: 294: 285: 284:Strobilurin F2 282: 266: 265: 256: 253: 229: 228: 219: 216: 200: 199: 190: 187: 179: 178: 169: 166: 157: 154: 124: 123: 114: 111: 109: 106: 78:pyraclostrobin 30: 13: 10: 9: 6: 4: 3: 2: 995: 984: 981: 979: 976: 974: 971: 969: 966: 965: 963: 953: 949: 937: 933: 932: 927: 917: 913: 912: 907: 906: 902: 893: 889: 884: 879: 875: 871: 867: 860: 857: 852: 848: 844: 840: 836: 832: 828: 824: 820: 816: 812: 810: 801: 799: 797: 795: 793: 791: 789: 785: 780: 774: 770: 766: 762: 755: 753: 751: 749: 747: 745: 743: 741: 739: 737: 733: 728: 724: 720: 716: 712: 708: 704: 700: 696: 689: 687: 685: 683: 679: 674: 668: 664: 660: 656: 649: 647: 645: 641: 637: 631: 625: 617: 610: 607: 602: 598: 594: 590: 586: 582: 575: 572: 568: 564: 560: 554: 551: 546: 542: 538: 534: 527: 524: 517: 513: 510: 509: 505: 499: 492: 487: 483: 476: 471: 467: 460: 455: 451: 444: 439: 437: 431: 429: 427: 426: 405: 401: 400: 395: 391: 390:basidiomycete 379: 372: 368: 367: 366: 360: 358: 356: 348: 344: 343: 340:Strobilurin X 339: 337: 336: 334: 329: 325: 321: 313: 309: 308: 305:Strobilurin H 304: 302: 300: 292: 288: 287: 283: 281: 279: 278: 273: 272: 263: 259: 258: 255:Strobilurin E 254: 252: 250: 249: 244: 240: 236: 235: 226: 222: 221: 217: 215: 213: 212: 207: 206: 197: 193: 192: 189:Strobilurin C 188: 186: 184: 183:S. tenacellus 176: 172: 171: 168:Strobilurin B 167: 165: 163: 155: 153: 151: 147: 143: 142: 141:Bolinea lutea 137: 136: 131: 130: 121: 117: 116: 113:Strobilurin A 112: 107: 105: 103: 100:, disrupting 99: 95: 91: 85: 83: 79: 75: 74:dimoxystrobin 71: 67: 66:fluoxastrobin 63: 62:picoxystrobin 59: 55: 51: 50: 44: 42: 38: 34: 26: 22: 18: 983:Strobilurins 951: 940:, retrieved 930: 920:, retrieved 910: 873: 869: 859: 814: 806: 760: 702: 698: 654: 624:cite journal 615: 609: 584: 580: 574: 558: 553: 536: 532: 526: 450:Azoxystrobin 435: 423: 403: 397: 393: 378:Oudemansin A 376: 364: 354: 352: 331: 327: 319: 317: 298: 296: 275: 269: 267: 246: 238: 232: 230: 209: 203: 201: 182: 180: 161: 159: 139: 133: 127: 125: 98:mitochondria 86: 70:oryzastrobin 54:azoxystrobin 47: 45: 17:Strobilurins 16: 15: 821:: 535–544. 410:= MeO and R 361:Oudemansins 277:Favolaschia 205:X. longipes 162:Favolaschia 41:Complex III 21:agriculture 968:Fungicides 962:Categories 942:2019-09-08 922:2019-09-08 518:References 328:C. anomala 102:metabolism 25:fungicides 843:0036-021X 727:246934805 719:1385-2728 418:= H and R 355:O. mucida 90:nutrients 936:archived 916:archived 851:95676421 636:pdf link 601:29711574 506:See also 333:Agaricus 324:phenolic 320:B. lutea 299:B. lutea 243:hydroxyl 239:B. lutea 823:Bibcode 392:fungus 892:528381 890:  849:  841:  775:  725:  717:  669:  599:  565:  380:with R 847:S2CID 817:(6). 807:[ 723:S2CID 280:spp. 164:spp. 888:PMID 839:ISSN 773:ISBN 715:ISSN 667:ISBN 630:link 597:PMID 563:ISBN 402:and 335:spp. 330:and 274:and 208:and 80:and 878:doi 831:doi 765:doi 707:doi 659:doi 589:doi 541:doi 537:111 384:= R 96:in 23:as 964:: 950:, 934:, 914:, 886:. 874:32 872:. 868:. 845:. 837:. 829:. 815:67 813:. 787:^ 771:. 735:^ 721:. 713:. 701:. 697:. 681:^ 665:. 643:^ 626:}} 622:{{ 595:. 585:38 583:. 535:. 428:. 357:. 301:. 251:. 214:. 185:. 138:, 132:, 84:. 76:, 72:, 68:, 64:, 60:, 56:, 43:. 33:Is 894:. 880:: 853:. 833:: 825:: 781:. 767:: 729:. 709:: 703:2 675:. 661:: 638:) 634:( 632:) 603:. 591:: 569:. 547:. 543:: 420:2 416:1 412:2 408:1 386:2 382:1 31:o 29:Q

Index

agriculture
fungicides
QoIs
respiratory chain
Complex III
Strobilurus tenacellus
azoxystrobin
kresoxim-methyl
picoxystrobin
fluoxastrobin
oryzastrobin
dimoxystrobin
pyraclostrobin
trifloxystrobin
nutrients
electron transfer
mitochondria
metabolism

Oudemansiella mucida
Strobilurus tenacellus
Bolinea lutea
geometric isomer
total synthesis


X. longipes
X. melanotricha

Cyphellopsis anomala

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