24:
267:
192:
723:
the discovery of a potentially toxic metabolite in technical grade PCNB to be used in fungicide formulations, the sale of PCNB was halted by the U.S. EPA until the issue could be resolved. In
November 2011, the EPA approved certain registrations for PCNB, allowing it back on the market for golf course turf, potato, cotton, ornamental bulb and cole crop uses in the United States. PCNB is used widely as a fungicide in other countries, such as China and Japan, however, "it is no longer approved for use within the European Union".
33:
444:
722:
In April 1993, PCNB was declared a hazardous air pollutant in the U.S. PCNB was reexamined for re-registration eligibility by the U.S. EPA in 2006 as part of the 1996 Food
Protection Quality Act (FPQA) and as a result, use on a number of crops were ended or limited. In August 2010, in response to
713:
PCNB is used as a fungicide to suppress the growth of fungi in various crops, such as cotton, rice, and seed grains. It is also used to prevent the formation of slime in industrial waters. Residual amounts of the compound and its metabolites can be found in crops. The degradation products, PCA and
811:
Sung-Kyu Shin; et al. (2003). "Isolation and
Identification of a Pentachloronitrobenzene (PCNB) Degrading bacterium Alcaligenes xylosoxidans PCNB-2 from Agricultural Soil".
739:
Cairns, Thomas; Siegmund, Emil G.; Krick, Fred (1987). "Identification of several new metabolites from pentachloronitrobenzene by gas chromatography/Mass spectrometry".
639:
576:
627:
109:
457:
828:"Determination of 17 kinds of Banned Organochlorine Pestides in Water by Activated Carbon Fiber-Solid Phase Microextraction Coupled with GC-MS"
626:
Although PCNB has a long shelflife, it is labile in soil, with a half life of 1.8 days. It degrades to other metabolites, mainly reducing to
316:
642:(PCTA). Another metabolite is methyl pentachlorophenyl sulfide (MPCPS). Little information is available about the degradation mechanisms.
923:
452:
911:
879:
1014:
495:
PCNB was originally synthesized in the laboratory in 1868. It was introduced to the agricultural world in the 1930s in
1019:
903:
775:
281:
464:
930:
522:. It can also be produced by the nitration of chlorinated benzenes. A side product of the synthesis of PCNB is
1029:
944:
224:
187:
245:
149:
969:
797:
262:
504:
23:
233:
45:
169:
8:
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874:(2nd ed.). Philadelphia, PA: Lippincott Williams & Wilkins. pp. 1111–1112.
572:
511:
75:
266:
191:
129:
85:
785:
907:
899:
875:
849:
771:
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523:
896:
Handbook of
Environmental Fate and Exposure Data for Organic Chemicals: Pesticides
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339:
213:
435:
1008:
401:
391:
180:
32:
853:
844:
827:
484:
752:
635:
510:. PCNB is prepared by chlorination of nitrobenzene at 60–70 °C in
423:
370:
160:
507:
434:
Except where otherwise noted, data are given for materials in their
519:
500:
487:. It is a off-white to yellow crystalline solid with a musty odor.
108:
951:. Golf Course Superintendents Association of America. 28 Nov 2011
924:"Reregistration Eligibility Decision for Pentachloronitrobenzene"
568:
496:
200:
515:
140:
714:
PCTA have been found in farming soils and in river sediments.
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120:
98:
250:
999:
Metabolism of pentachloronitrobenzene by goats and sheep
770:(electronic release 7th ed.). Weinheim: Wiley-VCH.
290:
InChI=1S/C6Cl5NO2/c7-1-2(8)4(10)6(12(13)14)5(11)3(1)9
300:
InChI=1/C6Cl5NO2/c7-1-2(8)4(10)6(12(13)14)5(11)3(1)9
738:
483:, is a registered fungicide formally derived from
872:Clinical Environmental Health and Toxic Exposures
526:(HCB), which is considered as hazardous as PCNB.
406:328 °C (622 °F; 601 K) decomposes
1006:
1001:; J Agric Food Chem. 1983 Nov-Dec; 31(6):1150-8.
212:
84:
945:"PCNB back on the market for golf course turf"
810:
825:
865:
863:
741:Journal of Agricultural and Food Chemistry
265:
190:
168:
843:
765:
232:
870:Sullivan, J. B.; Krieger, G. R. (2001).
860:
261:
1007:
396:144 °C (291 °F; 417 K)
181:
888:
293:Key: LKPLKUMXSAEKID-UHFFFAOYSA-N
148:
128:
759:
50:1,2,3,4,5-Pentachloro-6-nitrobenzene
303:Key: LKPLKUMXSAEKID-UHFFFAOYAW
203:
13:
579:, indicating its high reactivity:
14:
1041:
826:Tonghua Sun; et al. (2006).
562:
898:, CRC Press, 1991; pp. 551-553.
442:
357:
351:
31:
22:
991:
931:Environmental Protection Agency
708:
438:(at 25 °C , 100 kPa).
976:. National Library of Medicine
962:
937:
916:
819:
804:
732:
490:
360:
345:
324:O=()c1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl
1:
726:
717:
428:Slightly soluble in alcohols
386:Off-white or yellow crystals
7:
813:The Journal of Microbiology
10:
1046:
1015:Chlorobenzene derivatives
970:"Pentachloronitrobenzene"
768:Nitro Compounds, Aromatic
432:
332:
312:
277:
68:
56:
44:
39:
30:
21:
1020:Nitrobenzene derivatives
997:Aschbacher PW, Feil VJ,
479:, typically abbreviated
17:Pentachloronitrobenzene
477:Pentachloronitrobenzene
59:Pentachloronitrobenzene
845:10.2116/analsci.22.293
640:pentachlorothioanisole
1030:Endocrine disruptors
577:pentachlorophenetole
46:Preferred IUPAC name
753:10.1021/jf00075a037
630:(PCA), but also to
573:potassium hydroxide
512:chlorosulfuric acid
503:as a substitute to
413:Solubility in water
378: g·mol
18:
766:Booth, G. (2000).
628:pentachloroaniline
465:Infobox references
16:
912:978-0-87371-328-3
881:978-0-683-08027-8
632:pentachlorophenol
524:hexachlorobenzene
473:Chemical compound
471:
470:
246:CompTox Dashboard
110:Interactive image
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340:Chemical formula
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567:Reaction with
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563:Main reactions
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904:0-87371-328-1
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777:9783527306732
773:
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676:
658:+ 6 → C
645:
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402:Boiling point
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392:Melting point
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263:DTXSID2021105
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182:ECHA InfoCard
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992:Bibliography
978:. Retrieved
973:
964:
953:. Retrieved
948:
939:
918:
895:
890:
871:
838:(2): 293–8.
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812:
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712:
709:Applications
625:
566:
494:
485:nitrobenzene
480:
476:
475:
150:ChEMBL468759
69:Identifiers
57:Other names
980:28 November
794:|work=
491:Preparation
383:Appearance
333:Properties
188:100.001.305
130:CHEBI:34908
1025:Fungicides
1009:Categories
955:2013-05-28
949:GCSAA News
815:: 165–168.
727:References
718:Regulation
701:OH + HNO
636:hydrolysis
508:pesticides
424:Solubility
418:0.44 mg/L
371:Molar mass
234:Q37G40S4S8
161:ChemSpider
97:3D model (
76:CAS Number
63:Quintozene
832:Anal. Sci
796:ignored (
786:cite book
693:O → C
505:mercurial
854:16512425
558:+ 5 HCl
520:catalyst
501:Bayer AG
974:Pubchem
575:yields
569:ethanol
514:, with
497:Germany
458:what is
456: (
201:PubChem
86:82-68-8
910:
902:
878:
852:
774:
689:+ 6 H
670:+ 2 H
619:+ KNO
595:+ KOCH
516:iodine
453:verify
450:
376:295.32
317:SMILES
141:ChEMBL
40:Names
927:(PDF)
603:→ C
546:→ C
518:as a
282:InChI
121:ChEBI
99:JSmol
982:2022
908:ISBN
900:ISBN
876:ISBN
850:PMID
798:help
772:ISBN
638:and
571:and
534:+ C
530:5 Cl
481:PCNB
225:UNII
214:6720
170:6464
61:PCNB
840:doi
749:doi
611:OCH
499:by
251:EPA
204:CID
1011::
972:.
947:.
929:.
906:,
862:^
848:.
836:22
834:.
830:.
790::
788:}}
784:{{
745:35
743:.
697:Cl
685:NO
681:Cl
666:NH
662:Cl
654:NO
650:Cl
615:CH
607:Cl
599:CH
591:NO
587:Cl
554:NO
550:Cl
542:NO
352:Cl
984:.
958:.
933:.
884:.
856:.
842::
800:)
780:.
755:.
751::
703:2
699:5
695:6
691:2
687:2
683:5
679:6
677:C
674:O
672:2
668:2
664:5
660:6
656:2
652:5
648:6
646:C
621:2
617:3
613:2
609:5
605:6
601:3
597:2
593:2
589:5
585:6
583:C
556:2
552:5
548:6
544:2
540:5
538:H
536:6
532:2
448:N
364:2
361:O
358:N
355:5
349:6
346:C
253:)
249:(
101:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
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