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
915:
531:
Schramm, Georg; Steglich, Wolfgang; Anke, Timm; Oberwinkler, Franz (1978). "Antibiotika aus
Basidiomyceten, III. Strobilurin a und B, antifungische Stoffwechselprodukte aus Strobilurus tenacellus".
614:
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".
805:
Zakharychev, Vladimir V; Kovalenko, Leonid V (1998-06-30). "Natural compounds of the strobilurin series and their synthetic analogues as cell respiration inhibitors".
629:
935:
436:
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".
474:
929:
270:
808:
326:
hydroxy group in place of the aromatic methoxy group of strobilurin H is called strobilurin F1 and is found in
424:
233:
134:
48:
210:
982:
623:
458:
947:
822:
481:
465:
247:
204:
128:
81:
57:
967:
490:
140:
73:
65:
61:
635:
69:
19:
are a group of natural products and their synthetic analogs. A number of strobilurins are used in
846:
722:
365:
The oudemansins are closely related to the strobilurins and are also quinone outside inhibitors.
442:
887:
838:
772:
714:
694:
666:
596:
562:
398:
93:
36:
877:
830:
764:
706:
658:
588:
540:
145:
511:
149:
388:= H was first described in 1979, after being isolated from mycelial fermentations of the
826:
46:
The first parent natural products, strobilurins A and B, were extracted from the fungus
818:
497:
77:
710:
961:
726:
389:
850:
834:
449:
377:
370:
97:
53:
882:
865:
768:
662:
593:
10.1002/(SICI)1521-3773(19990517)38:10<1328::AID-ANIE1328>3.0.CO;2-1
276:
40:
20:
101:
842:
718:
544:
290:
24:
864:
Anke, Timm; Hecht, Hans Jürgen; Chramm, Georgs; Steglich, Wolfgang (1979).
600:
557:
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
28:
800:
798:
796:
794:
792:
790:
788:
396:. Later it was found in cultures of the basidiomycete fungi
653:
Schaefer, Bernd (2014). "Agrochemicals: 8.2 Strobilurins".
931:
Agricultural mycocides for the 21st century: strobilurins
759:
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:
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899:
863:
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858:
804:
803:
786:
779:
758:
757:
734:
692:
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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
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