Compounds > isopropalin
Page last updated: 2024-11-06

isopropalin

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Isopropalin is a pre-emergent herbicide used to control broadleaf weeds in various crops, such as soybeans, peanuts, and cotton. Its synthesis involves a multi-step process that begins with the reaction of 2,6-dichloroaniline with 2-methyl-1-propanol. This reaction forms a key intermediate, which is then reacted with isobutylene oxide to yield isopropalin. Isopropalin inhibits the growth of weeds by disrupting the formation of microtubules, which are essential for cell division and growth. It has been found to be effective in controlling a wide range of weed species, including pigweed, ragweed, and crabgrass. Its use in agriculture has been crucial for maintaining crop yields and minimizing weed competition. Due to its effectiveness and environmental impact, isopropalin has been extensively studied to understand its fate and transport in the environment. Researchers investigate its degradation pathways, potential leaching into groundwater, and its effects on non-target organisms. '

isopropalin: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID36606
CHEMBL ID1256728
CHEBI ID82189
SCHEMBL ID55296
MeSH IDM0051842

Synonyms (48)

Synonym
4-isopropyl-2,6-dinitro-n,n-dipropylaniline
brn 2762577
paarlan
epa pesticide chemical code 100201
isopropaline [iso-french]
hsdb 6687
cumidine, 2,6-dinitro-n,n-dipropyl-
2,6-dinitro-n,n-dipropylcumidine
caswell no. 506a
el-179
aniline, 2,6-dinitro-n,n-dipropyl-p-isopropyl-
isopropaline
2,6-dinitro-n,n-dipropyl-4-isopropylaniline
4-(1-methylethyl)-2,6-dinitro-n,n-dipropylbenzenamine
isopropalin [ansi:bsi:iso]
einecs 251-690-7
benzenamine, 4-(1-methylethyl)-2,6-dinitro-n,n-dipropyl-
isopropalin
33820-53-0
(4-isopropyl-2,6-dinitrophenyl)dipropylamine
4-isopropyl-2,6-dinitro-n,n-dipropyl-aniline
2,6-dinitro-4-propan-2-yl-n,n-dipropylaniline
NCGC00248025-02
NCGC00248025-01
C19063
CHEMBL1256728
chebi:82189 ,
NCGC00259777-01
cas-33820-53-0
tox21_300422
dtxsid8024157 ,
tox21_202228
NCGC00254366-01
dtxcid904157
unii-52gzd1i41n
52gzd1i41n ,
AKOS015892015
SCHEMBL55296
isopropalin [mi]
isopropalin [hsdb]
isopropalin [iso]
NEKOXWSIMFDGMA-UHFFFAOYSA-N
n-(4-isopropyl-2,6-dinitrophenyl)-n,n-dipropylamine #
el 179
isopropalin, pestanal(r), analytical standard
isopropalin, analytical standard
J-019332
Q27155794

Research Excerpts

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
C-nitro compoundA nitro compound having the nitro group (-NO2) attached to a carbon atom.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
GLI family zinc finger 3Homo sapiens (human)Potency2.73060.000714.592883.7951AID1259369
AR proteinHomo sapiens (human)Potency39.36140.000221.22318,912.5098AID1259243; AID743035; AID743042; AID743063
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency16.82220.001022.650876.6163AID1224838; AID1224839
progesterone receptorHomo sapiens (human)Potency33.64340.000417.946075.1148AID1346795
retinoid X nuclear receptor alphaHomo sapiens (human)Potency19.09140.000817.505159.3239AID1159531
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency67.12740.001530.607315,848.9004AID1224841
pregnane X nuclear receptorHomo sapiens (human)Potency21.57440.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency23.86600.000229.305416,493.5996AID743069; AID743075
thyroid stimulating hormone receptorHomo sapiens (human)Potency7.77520.001628.015177.1139AID1224843; AID1224895
thyroid hormone receptor beta isoform 2Rattus norvegicus (Norway rat)Potency64.12900.000323.4451159.6830AID743065; AID743067
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID522809Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin H28Q mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522806Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin V4L mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522816Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243S mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522812Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235T mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522810Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin L136F mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522808Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin F24H mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522805Antimicrobial activity against Toxoplasma gondii RH infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522807Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin S6I mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522813Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235V mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522811Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin I235L mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522815Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin R243C mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
AID522814Antimicrobial activity against Toxoplasma gondii RH containing alpha1-tubulin T239I mutation infected in HFF cells by plaque assay2010Antimicrobial agents and chemotherapy, Apr, Volume: 54, Issue:4
Dinitroaniline activity in Toxoplasma gondii expressing wild-type or mutant alpha-tubulin.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (33.33)18.7374
1990's0 (0.00)18.2507
2000's2 (33.33)29.6817
2010's1 (16.67)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 26.49

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index26.49 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.14 (4.65)
Search Engine Demand Index29.80 (26.88)
Search Engine Supply Index2.60 (0.95)

This Compound (26.49)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
acetone
methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).		2.0310ketone body;
methyl ketone;
propanones;
volatile organic compound		EC 3.5.1.4 (amidase) inhibitor;
human metabolite;
polar aprotic solvent
benefin
benefin: structure. benfluralin : A tertiany amino compound that is 2,6-dinitro-4-(trifluoromethyl)aniline in which the hydrogens attached to the aniline nitrogen have been replaced by one ethyl and one butyl group. It is used as a pre-emergence herbicide used for the control of grass and other weeds in a range of food and non-food crops.		2.420C-nitro compound;
organofluorine compound;
substituted aniline;
tertiary amino compound		agrochemical;
herbicide
metolachlor
metolachlor: structure given in first source. metolachlor : A racemate that consists of equimolar amounts of (R)- and (S)-metolachlor.. 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide : An organochlorine compound that is 2-chloroacetamide substituted by a (2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl) group at the nitrogen atom.		2.0310aromatic amide;
benzenes;
ether;
organochlorine compound
trifluralin
Trifluralin: A microtubule-disrupting pre-emergence herbicide.. trifluralin : A substituted aniline that is N,N-dipropylaniline substituted by a nitro groups at positions 2 and 6 and a trifluoromethyl group at position 4. It is an agrochemical used as a pre-emergence herbicide.		2.420(trifluoromethyl)benzenes;
C-nitro compound;
substituted aniline		agrochemical;
environmental contaminant;
herbicide;
xenobiotic
alanine
Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.		2.0310alanine zwitterion;
alanine;
L-alpha-amino acid;
proteinogenic amino acid;
pyruvate family amino acid		EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor;
fundamental metabolite
chloroform
Chloroform: A commonly used laboratory solvent. It was previously used as an anesthetic, but was banned from use in the U.S. due to its suspected carcinogenicity.. chloroform : A one-carbon compound that is methane in which three of the hydrogens are replaced by chlorines.		1.9510chloromethanes;
one-carbon compound		carcinogenic agent;
central nervous system drug;
inhalation anaesthetic;
non-polar solvent;
refrigerant
nitralin
nitralin: structure		2.0510C-nitro compound
oryzalin
oryzalin: a dinitroaniline; preemergence herbicide; structure. oryzalin : A sulfonamide that is benzenesulfonamide substituted at positions 3 and 5 by nitro groups and at position 4 by a dipropylamino group.		2.7230aromatic amine;
C-nitro compound;
sulfonamide;
tertiary amino compound		agrochemical;
antimitotic;
herbicide
profluralin
[no description available]		2.0510C-nitro compound
dinitramine
dinitramine: structure		2.0510C-nitro compound
fluchloralin
fluchloralin: structure		2.0510C-nitro compound
butralin
butralin: structure		7.7630C-nitro compound
pendimethalin
pendimethalin : A member of the class of substituted anilines that is N-(pentan-3-yl)aniline bearing two additional nitro substituents at positions 2 and 6 as well as two methyl substituents at positions 3 and 4. A herbicide used to control most annual grasses and many annual broad-leaved weeds.		7.9740C-nitro compound;
secondary amino compound;
substituted aniline		agrochemical;
environmental contaminant;
herbicide
ethafluralin
[no description available]		2.0510C-nitro compound
metalaxyl
metalaxyl: RN given refers to (DL-Ala)-isomer. metalaxyl : A racemate comprising equal amounts of (R)- and (S)-metalaxyl. A systemic fungicide, it is active against phytopathogens of the order Peronosporales and is used to conrtrol Pythium in a number of vegetable crops.. methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate : An alanine derivative that is methyl alaninate in which one of the hydrogens attached to the nitrogen is substituted by a methoxyacetyl group, while the other is substituted by a 2,6-dimethylphenyl group.		2.0310alanine derivative;
aromatic amide;
carboxamide;
ether;
methyl ester
florisil
Florisil: hard, porous, granular substance used in vitamin analysis, chromatography, & antibiotic processing		2.0310
amiprophos methyl
amiprophos methyl: structure		2.0510
n1-phenyl-3,5-dinitro-n4,n4-di-n-propylsulfanilamide
N1-phenyl-3,5-dinitro-N4,N4-di-n-propylsulfanilamide: a potent, selective antimitotic agent against kinetoplastid parasites; structure in first source		2.0510
dinitrobenzenes
Dinitrobenzenes: Benzene derivatives which are substituted with two nitro groups in the ortho, meta or para positions.		2.4320
ConditionIndicatedRelationship StrengthStudiesTrials