nitralin

{{Short description|Weed control herbicide}}

{{Chembox

| Reference ={{cite web |title=Nitralin data sheet |url=http://www.bcpcpesticidecompendium.org/nitralin.html |website=www.bcpcpesticidecompendium.org |publisher=Compendium of Pesticide Common Names}}

| ImageFile = Nitralin.svg

| ImageSize =180px

| PIN =4-(methylsulfonyl)-2,6-dinitro-N,N-dipropylaniline

| OtherNames = Nitralin; Planavin; SD 11831; 4-(Methylsulfonyl)-2,6-dinitro-N,N-dipropylbenzenamine

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 19622

| EC_number = 225-219-0

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19064

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 82190

| StdInChI=1S/C13H19N3O6S/c1-4-6-14(7-5-2)13-11(15(17)18)8-10(23(3,21)22)9-12(13)16(19)20/h8-9H,4-7H2,1-3H3

| StdInChIKey = UMKANAFDOQQUKE-UHFFFAOYSA-N

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1256763

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 4726-14-1

| PubChem =20848

| UNII_Ref =

| UNII = 697W0VS4HQ

| UNNumber = 3077

| SMILES = CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])S(=O)(=O)C)[N+](=O)[O-]

}}

|Section2={{Chembox Properties

| C=13|H=19|N=3|O=6|S=1

| Appearance = Yellow/orange powder

| Odour = Mild odour{{cite web |last1=U.S. Coast Guard |title=Chemical Hazards Response Information System (CHRIS) Hazardous Chemical Data; Commandant Instruction 16465.12C |url=https://hero.epa.gov/hero/index.cfm/reference/details/reference_id/5208492 |publisher=Department of Transportation |access-date=11 October 2024 |location=Washington, DC |format=Technical Report |date=1999}}

| Density = 1.001{{cite web |last1=Boyer |first1=Kevin R. |last2=Hodge |first2=Virginia E. |last3=Wetzel |first3=Roger S. |last4=Science Applications International Corporation |title=Handbook: Responding to Discharges of sinking Hazardous Substances; EPA/540/2-87/001 |url=https://nepis.epa.gov/Exe/ZyNET.exe/10001HBK.txt?ZyActionD=ZyDocument&Client=EPA&Index=1986%20Thru%201990&Docs=&Query=%28nitralin%29%20OR%20FNAME%3D%2210001HBK.txt%22%20AND%20FNAME%3D%2210001HBK.txt%22&Time=&EndTime=&SearchMethod=1&TocRestrict=n&Toc=&TocEntry=&QField=&QFieldYear=&QFieldMonth=&QFieldDay=&UseQField=&IntQFieldOp=0&ExtQFieldOp=0&XmlQuery=&File=D%3A%5CZYFILES%5CINDEX%20DATA%5C86THRU90%5CTXT%5C00000000%5C10001HBK.txt&User=ANONYMOUS&Password=anonymous&SortMethod=h%7C-&MaximumDocuments=1&FuzzyDegree=0&ImageQuality=r75g8/r75g8/x150y150g16/i425&Display=hpfr&DefSeekPage=x&SearchBack=ZyActionL&Back=ZyActionS&BackDesc=Results%20page&MaximumPages=1&ZyEntry=2&SeekPage=f |publisher=Environmental Protection Agency |date=September 1987}}

| MeltingPtC = 151

| MeltingPt_notes =

| BoilingPtF = 437

| BoilingPt_notes = (decomposes)

| Solubility =0.0006 g/L

| Solvent1 = acetone

| Solubility1 = Soluble

| VaporPressure = 0.2 x10⁻⁶ mm Hg (25°C){{cite journal |last1=Huffman |first1=J. B. |last2=Camper |first2=N. D. |title=Growth Inhibition in Tobacco (Nicotiana tabacum) Callus by 2,6-Dinitroaniline Herbicides and Protection by D-α-Tocopherol Acetate |journal=Weed Science |date=1978 |volume=26 |issue=6 |pages=527–530 |doi=10.1017/S0043174500064468 |jstor=4042920 |url=https://www.jstor.org/stable/4042920 |issn=0043-1745}}

}}

|Section3={{Chembox Hazards

| GHS_ref= {{cite web |title=Safety data sheet according to 1907/2006/EC, Article 31 |url=https://www.lgcstandards.com/DE/en/Nitralin/p/DRE-C15540000# |website=www.lgcstandards.com |publisher=LGC Standards |access-date=11 October 2024 |format=PDF |date=9 July 2019}}

| MainHazards =

| GHSPictograms = {{GHS09}}

| HPhrases = {{H-phrases|228|410}}

| PPhrases = {{P-phrases|273|391|501}}

| LD50 = >5000 mg/kg (rats and mice); >2000 mg/kg (waterfowl)

| LC50 = 46 mg/L (fish)

| FlashPt =

| AutoignitionPtF = 435

}}

}}

Nitralin is a selective pre-emergent dinitroaniline herbicide{{cite web |title=Planavin 75 Herbicide Wettable Powder |url=https://www3.epa.gov/pesticides/chem_search/ppls/000201-00167-19670313.pdf |publisher=Shell Plc |access-date=11 October 2024}} that is closely related to trifluralin, and released two years later in 1966. Today it is largely obsolete. It was used in the USA, France and Australia to control annual grasses and broad-leaved weeds, and was applied on vines, crops{{cite web |title=Nitralin (Ref: HSDB 789) |url=http://sitem.herts.ac.uk/aeru/ppdb/en/Reports/1284.htm |website=Pesticide Properties Database |publisher=University of Hertfordshire |access-date=10 October 2024}}{{cite web |last1=Elite |first1=Trademark |title=PLANAVIN, An Australia Trademark of Shell International Petroleum Co Limited. Application Number: 204428 :: Trademark Elite Trademarks |url=https://www.trademarkelite.com/australia/trademark/trademark-detail/204428/PLANAVIN |website=www.trademarkelite.com |language=en}}{{cite journal |last1=Boulanger |first1=Mathilde |last2=Tual |first2=Séverine |last3=Lemarchand |first3=Clémentine |last4=Baldi |first4=Isabelle |last5=Clin |first5=Bénédicte |last6=Lebailly |first6=Pierre |journal=Occupational & Environmental Medicine |title=0441 Exposure to dinitroanilines and risk of lung cancer (Lc) by subtypes: Results from the agrican cohort |date=August 2017 |volume=74 |issue=Suppl 1|page=A140.1 |doi=10.1136/oemed-2017-104636.365}} and turf.

American farmers used {{convert|405,000|lbs|t}} in 1974, though trifluralin still overshadowed it, with {{convert|22,960,000|lbs|t}}.{{cite web |title=Pesticide Usage Survey of Agricultural, Governmental, and Industrial Sectors in the United States, 1974 |url=https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=91012P4O.txt |website=epa.gov |publisher=EPA |date=1977}} A 1992 report mentions extensive use on potatoes,{{cite journal |last1=Thriveni |first1=T. |last2=Rajesh Kumar |first2=J. |last3=Sujatha |first3=D. |last4=Sreedhar |first4=N.Y. |title=Voltammetric determination of the herbicides nitralin and oryzalin in agricultural formulations, vegetables and grape juice samples |journal=Food Chemistry |date=January 2007 |volume=104 |issue=3 |pages=1304–1309 |doi=10.1016/j.foodchem.2006.10.014}} though Shell's "Planavin" trademark expired in 1989.{{cite web |last1=Elite |first1=Trademark |title=Trademark Search and Trademark Registration - Register a Trademark and File Your Trademark Application Online |url=https://www.trademarkelite.com/trademark/trademark-search.aspx?sw=planavin&hline= |access-date=11 October 2024 |language=en}}

On ryegrass meristems, nitralin suppressed elongation and made the roots wider. After 1 hour, mitosis was reduced by 76%. Cell nuclei expanded, becoming polymorphic, and with increased ploidy levels. Other dinitroanilines have similar effects, except butralin.{{cite journal |last1=Elmore |first1=C. L. |last2=Bayer |first2=D. E. |title=Mitotic and structural effects of nitralin and butralin on ryegrass ( Lolium perenne L.) root meristems |journal=Weed Research |date=April 1992 |volume=32 |issue=2 |pages=77–86 |doi=10.1111/j.1365-3180.1992.tb01864.x}}

Nitralin is not associated with lung cancer.