248:
173:
24:
1316:"Commission Regulation (EU) No 1004/2013 of 15 October 2013 amending Annexes II and III to Regulation (EC) No 396/2005 of the European Parliament and of the Council as regards maximum residue levels for 8-hydroxyquinoline, cyproconazole, cyprodinil, fluopyram, nicotine, pendimethalin, penthiopyrad and trifloxystrobin in or on certain products Text with EEA relevance"
718:
in soybeans, and in 2008, it issued a
Section 3 registration. In 2009, Syngenta applied for full registration of cyproconazole use on soybean. In 2012, Syngenta requested the EPA to establish regulations for residues of cyproconazole in or on peanut including nutmeat, peanut hay, peanut meal, peanut
690:
Development of fungal resistance can be prevented by not using cyproconazole "repeatedly alone in the same season" or by not using it late in the infection, that is, curatively. Fungi can develop resistance if the same fungicide is used repeatedly or when fungicides with the same mode of action are
619:
has classified cyproconazole into carcinogen category 3 as limited evidence, into the reproduction risk category 3 as "possible risk of harm to the unborn child", as harmful if swallowed, and dangerous for the environment, because it is very toxic to aquatic organisms, causing long-term adverse
620:
effects in the aquatic environment. While it is moderately toxic to mammals and most aquatic organisms, earthworms and honeybees, it is highly toxic to birds. In sandy loam soil, half life was 148 days.
467:, causing acute and long-term adverse effects in the aquatic environment. While it is moderately toxic to mammals and most aquatic organisms, earthworms and honeybees, it is highly toxic to birds.
1005:
Tamura K, Inoue K, Takahashi M, et al. (April 2015). "Involvement of constitutive androstane receptor in liver hypertrophy and liver tumor development induced by triazole fungicides".
487:. This explains why it must be used, when fungal growth is at a maximum, early in the infection, because in late infections fungal growth slows down and the agent is ineffective.
704:
1091:
Konwick BJ, Garrison AW, Avants JK, Fisk AT (December 2006). "Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss)".
1388:
612:
448:
878:
297:
1149:
914:
787:
710:
In 2006, EPA settled with
Syngenta for $ 15,600, because they failed to report cyproconazole production in India and Switzerland. In 2007, the
1266:
1127:
915:"Review report for the active substance cyproconazole finalised in the Standing Committee on the Food Chain and Animal Health, 11 March 2011"
1220:
711:
1175:
573:
90:
564:, and applied by air or on the ground to cereal crops, coffee, sugar beet, fruit trees and grapes. It controls the following pests:
1383:
262:
1221:"Registration of Alto 100 SL (EPA Reg. No. 100-1226) Which Contains the New Active Ingredient Cyproconazole (Chemical Code 128993)"
941:
639:
521:
714:
had issued a
Section 18 quarantine exemption for using Syngenta's then unregistered cyproconazole product "Alto 100 SL" against
1197:
1042:"Combination effects of (tri)azole fungicides on hormone production and xenobiotic metabolism in a human placental cell line"
728:
976:
1368:
885:
1150:"U.S. EPA settles with agribusiness firm for $ 15,600 for failing to report pesticides produced in India and Switzerland"
731:
recommended cyproconazole be registered in 2010. Approval began in June 2011 and expired after 10 years in May 2021. The
385:
205:
226:
1373:
736:
628:
581:
1363:
1345:, Pesticide Properties DataBase, University of Hertfordshire, U.K., 26 June 2015, accessed 19 September 2015
965:, Pesticide Properties DataBase, University of Hertfordshire, U.K., 26 June 2015, accessed 19 September 2015
732:
1291:
1244:
271:
InChI=1S/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3
168:
1378:
603:
penetration. The re-entry interval is 12 hours. Reapplication within 30 days of harvest is not permitted.
401:
281:
InChI=1/C15H18ClN3O/c1-11(12-2-3-12)15(20,8-19-10-17-9-18-19)13-4-6-14(16)7-5-13/h4-7,9-12,20H,2-3,8H2,1H3
130:
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624:
456:
36:
580:
species. It can be used on above-ground wood to prevent it from decay from fungi as an alternative to
1358:
821:
643:
611:
Cyproconazole is moderately soluble in water and has a high risk of leaching to groundwater. It is
243:
56:
715:
616:
452:
1108:
1073:
1022:
565:
537:
525:
1245:"Pesticide Petitions Filed for Residues of Pesticide Chemicals in or on Various Commodities"
1100:
1063:
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1040:
Rieke S, Koehn S, Hirsch-Ernst K, Pfeil R, Kneuer C, Marx-Stoelting P (September 2014).
962:
942:"cyproconazole - Registration of Sentinel 40 WG Turf Fungicide (EPA Reg. No. 55947-132)"
623:
In EPA's 2011 predictive model of reproductive toxicity cyproconazole was shown to be a
110:
1068:
1041:
638:, a triazole used in human medicine, can induce liver swelling in mice. As of 2015 the
553:
509:
421:
379:
1352:
853:. University of Wisconsin extension service, Cooperative Extension in coop. with USDA
751:
vary from 0.05 mg/kg for most vegetables up to 0,1 mg/kg in stone fruit and cereals.
505:
476:
367:
161:
848:"Fungicide resistance management in corn, soybean, and wheat in Wisconsin NPM A3878"
647:
529:
517:
479:, a particular step in the synthesis of a component of the fungal cell wall called
1104:
977:"Predictive Model of Reproductive Toxicity from ToxCast High Throughput Screening"
194:
1315:
984:
Office of
Research & Development National Center for Computational Toxicology
797:. Food and Agriculture Organization of the United Nations (FAO). pp. 766–938
707:(FIFRA) with the U.S. EPA, and cyproconazole was approved on December 22, 1993.
635:
592:
513:
484:
455:
has classified cyproconazole into carcinogen category 3 as limited evidence, as
433:
409:
447:. EU approval began in June 2011 and expired after 10 years in May 2021. It is
1018:
913:
EUROPEAN COMMISSION HEALTH & CONSUMERS DIRECTORATE-GENERAL (7 July 2015).
671:
667:
561:
439:
In the US approval began in 1993, and it was introduced to the market by then
429:
354:
141:
1058:
767:
679:
1176:"Office of Pesticide Programs Emergency Exemption Static PageCyproconazole"
1112:
1077:
1026:
23:
739:
is 0.02 mg/kg body weight per day. Cyproconazole is registered under the
528:
in two foliar fungicides for soybeans in the U.S.: Alto X, and mixed with
1219:
New York State
Department of Environmental Conservation (July 14, 2009).
659:
577:
569:
533:
501:
460:
444:
822:"Chromated Copper Arsenate (CCA): Cyproconazole - An Alternative to CCA"
599:
with 5 gallon per acre; ground application is adequate for coverage and
1198:"Syngenta's Alto fungicide receives Section 3 registration in soybeans"
181:
700:
480:
440:
121:
378:
Except where otherwise noted, data are given for materials in their
642:
has been shown to be mediator for this effect. Cyproconazole is an
405:
101:
89:
79:
727:
In Europe, Syngenta had applied for registration in 2009 and the
719:
butter and refined oil, which as of 2015 was still under review.
786:
Joint FAO/WHO Meeting on
Pesticide Residues (24 February 2011).
744:
557:
425:
413:
412:, coffee, sugar beet, fruit trees and grapes, and peanuts, on
231:
884:. University of Nebraska–Lincoln. p. 1. Archived from
646:
and has been shown to cause a dose dependent inhibition of
483:. This means it affects fungal growth, but not the fungal
674:
synthesis. In fish, CYP mediated steroid metabolism and
877:
Tom
Weissling, Plant Disease Central (26 January 2010).
420:
and on wood as a preservative. It has been used against
584:. It was originally marketed for use on sod farms and
520:, and copper. In wood preservatives it is mixed with
705:
595:is allowed with less than half inch application,
1247:. US Environmental Protection Agency. 9 May 2012
193:
65:
650:production in human placental cells in vitro.
691:repeatedly.(package insert Alto 100Syngenta)
682:of cyproconazole in trout was about one day.
8:
846:Paul Esker; Richard Proost (December 2010).
432:, and applied by air or on the ground or by
372:107.5 °C (225.5 °F; 380.6 K)
703:applied in 1988 for registration under the
246:
171:
149:
15:
1067:
1057:
213:
1292:"Substance Information - cyproconazole"
759:
500:Many different formulations exist with
302:
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242:
986:. U.S. Environmental Protection Agency
678:can be affected in opposite ways. The
162:
1389:Lanosterol 14α-demethylase inhibitors
872:
870:
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814:
812:
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779:
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274:Key: UFNOUKDBUJZYDE-UHFFFAOYSA-N
129:
109:
40:2-(4-Chlorophenyl)-3-cyclopropyl-1-(1
7:
908:
906:
841:
839:
712:U.S. Environmental Protection Agency
615:in both soil and water systems. The
451:in both soil and water systems. The
574:Pseudocercosporella herpotrichoides
443:in 1994, which as of 2000 has been
305:CC(C1CC1)C(Cn2cncn2)(c3ccc(cc3)Cl)O
284:Key: UFNOUKDBUJZYDE-UHFFFAOYAK
184:
666:, so it can no longer demethylate
14:
879:"Soybean foliar fungicides table"
795:2010 JMPR Monograph - Agriculture
1200:. Delta Farm Press. May 23, 2008
640:constitutive androstane receptor
522:didecyldimethylammonium chloride
341:
338:
332:
22:
1046:Int J Environ Res Public Health
465:very toxic to aquatic organisms
382:(at 25 °C , 100 kPa).
1128:"FR Doc. 94-7703 Filed 4-5-94"
975:Matthew Martin (26 May 2011).
729:European Food Safety Authority
552:Cyproconazole is used against
504:, difenoconazole, prochloraz,
347:
326:
44:-1,2,4-triazol-1-yl)-2-butanol
1:
1105:10.1016/j.aquatox.2006.10.003
766:Record for CAS#94361-06-5 in
536:. It is also manufactured by
461:dangerous for the environment
670:, an intermediate needed in
1290:European Chemicals Agency.
1178:. US EPA. 18 September 2015
1156:. US EPA. 20 September 2006
1154:News Releases from Region 9
1405:
1019:10.1016/j.fct.2015.01.021
737:European Chemicals Agency
629:high-throughput screening
582:Chromated Copper Arsenate
532:in Quadris Xtra, both by
376:
313:
293:
258:
49:
35:
30:
21:
1384:4-Chlorophenyl compounds
1267:"EU Pesticides Database"
747:. Since 2013, permitted
1059:10.3390/ijerph110909660
733:acceptable daily intake
658:Cyproconazole as other
475:Cyproconazole inhibits
940:EPA (September 1995).
919:EU Pesticides database
749:maximum residue levels
402:agricultural fungicide
676:xenobiotic metabolism
625:reproductive toxicant
457:reproductive toxicant
1369:Triazole antifungals
662:inhibits the enzyme
607:Hazards, ecotoxicity
891:on 23 November 2012
644:endocrine disruptor
634:Cyproconazole like
471:Mechanism of action
362: g·mol
18:
1130:. Federal Register
1007:Food Chem. Toxicol
824:. EPA. 2 July 2014
716:Asian soybean rust
617:European Community
453:European Community
386:Infobox references
16:
1374:Tertiary alcohols
1322:. 15 October 2013
1320:eur-lex.europa.eu
686:Fungal resistance
566:Puccinia graminis
538:Bayer CropScience
526:active ingredient
394:Chemical compound
392:
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227:CompTox Dashboard
91:Interactive image
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741:REACH Regulation
664:cytochrome P-450
586:golf course turf
560:on cereals and
542:Dow AgroSciences
428:on cereals and
418:golf course turf
404:of the class of
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512:, cyprodinil,
510:chlorothalonil
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1271:ec.europa.eu
1270:
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893:. Retrieved
886:the original
855:. Retrieved
826:. Retrieved
799:. Retrieved
794:
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709:
699:In the U.S.
698:
689:
657:
648:progesterone
633:
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610:
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551:
530:azoxystrobin
524:. It is the
518:azoxystrobin
499:
496:Formulations
474:
438:
410:cereal crops
397:
396:
50:Identifiers
41:
636:fluconazole
593:chemigation
548:Application
514:fludioxonil
485:sporulation
434:chemigation
314:Properties
169:100.130.443
111:CHEBI:83748
1359:Fungicides
1353:Categories
1326:2024-06-03
1301:2024-06-03
1276:2024-06-03
755:References
695:Regulation
672:ergosterol
668:lanosterol
613:persistent
562:apple scab
463:, because
449:persistent
430:apple scab
416:farms and
408:, used on
355:Molar mass
215:622B9C3E6T
142:ChemSpider
78:3D model (
67:94361-06-5
57:CAS Number
37:IUPAC name
1013:: 86–95.
768:SciFinder
743:with the
680:half-life
660:triazoles
459:, and as
1113:17118468
1078:25233012
1027:25656644
735:per the
578:Septoria
570:Puccinia
534:Syngenta
502:imazalil
445:Syngenta
1069:4199042
182:PubChem
1229:4 June
1134:4 June
1111:
1076:
1066:
1025:
948:4 June
857:4 June
828:4 June
801:4 June
723:Europe
701:Sandoz
601:canopy
572:spp.,
481:sterol
441:Sandoz
406:azoles
400:is an
360:291.78
298:SMILES
122:ChEMBL
31:Names
1224:(PDF)
1126:EPA.
980:(PDF)
944:. EPA
889:(PDF)
882:(PDF)
851:(PDF)
791:(PDF)
263:InChI
195:86132
151:77706
102:ChEBI
80:JSmol
1253:2015
1231:2015
1206:2015
1184:2015
1162:2015
1136:2015
1109:PMID
1074:PMID
1023:PMID
992:2015
950:2015
927:2015
921:. EU
897:2015
859:2015
830:2015
803:2015
745:ECHA
576:and
558:rust
540:and
426:rust
206:UNII
1101:doi
1064:PMC
1054:doi
1015:doi
491:Use
414:sod
232:EPA
185:CID
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348:O
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342:N
333:H
327:C
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42:H
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