Page last updated: 2024-11-05

diphenamid

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

Description

Diphenamid is a selective pre-emergence herbicide used to control a wide range of annual grasses and broadleaf weeds in various crops, including corn, soybeans, and cotton. It is a member of the propionic acid family of herbicides. Diphenamid is synthesized by reacting 2,6-dichloro-N,N-dipropylbenzamide with sodium hydroxide. The resulting sodium salt is then acidified to produce the free acid, diphenamid. Diphenamid acts by inhibiting cell division in germinating seeds. It disrupts the synthesis of microtubules, which are essential for cell division and elongation. Diphenamid is applied to the soil surface and incorporated into the top layer before crop emergence. It is also used as a soil fumigant. Diphenamid is relatively persistent in the soil and can remain active for several months. Its persistence in the environment has raised concerns about its potential to contaminate water sources. Diphenamid is also a known endocrine disruptor, meaning it can interfere with the hormonal systems of animals and humans. Its use has been restricted in some countries due to these concerns. Diphenamid is studied to understand its effects on different organisms, including plants, animals, and humans. Researchers are investigating ways to reduce its environmental impact and minimize its potential health risks.'

diphenamid: do not confuse with anti-inflammatory agent difenpiramide; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID13728
CHEMBL ID2252192
CHEBI ID81915
SCHEMBL ID39339
MeSH IDM0046050

Synonyms (76)

Synonym
CBMICRO_004881
unii-6z3r6ega2b
6z3r6ega2b ,
difenamid
dimethylamid kyseliny difenyloctove
5104-31-4
benzeneacetamide, n,n-dimethyl-.alpha.-phenyl-
acetamide, n,n-dimethyl-2,2-diphenyl-
ICCB1_000103
diphenamid [ansi:bsi:iso]
dymid
2,2-diphenyl-n,n-dimethylacetamide
dimethylamid kyseliny difenyloctove [czech]
dimid
diherbid
lilly 34,314
ent-28567
l-34314
rideon
hsdb 367
benzeneacetamide, n,n-dimethyl-alpha-phenyl-
u 4513
n,n-dimethyl-alpha-phenylbenzeneacetamide
zarur
epa pesticide chemical code 036601
difenamide [iso-french]
caswell no. 395
trefmid
n,n,dimethyl-2,2-diphenylacetamide
enide 50
enide
enide 50w
difenamide
dif 4
difenamid [czech]
fenam
einecs 213-482-4
n,n-dimethyldiphenylacetamide
brn 2052009
BIM-0004804.P001
diphenamid
n,n-dimethyl-2,2-diphenylacetamide
957-51-7
inchi=1/c16h17no/c1-17(2)16(18)15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12,15h,1-2h
AKOS002959926
NCGC00249013-01
C18722
NCGC00256969-01
tox21_303077
dtxcid304072
dtxsid8024072 ,
cas-957-51-7
tox21_201282
NCGC00258834-01
smsf0003236
CB06865
FT-0633188
CHEMBL2252192
diphenamide
chebi:81915 ,
diphenamid [hsdb]
n,n-dimethyl-.alpha.-phenylbenzeneacetamide
n,n-dimethyl-.alpha.,.alpha.-diphenyl acetamide
diphenamid [mi]
diphenamid [iso]
SCHEMBL39339
n,n-dimethyl-alpha,alpha-diphenylacetamide
n,n-dimethyl-.alpha.,.alpha.-diphenylacetamide
cambridge id 5104314
SR-01000195224-1
sr-01000195224
diphenamid, pestanal(r), analytical standard
Z32014572
n,n-dimethyl-a-phenylbenzene ethanamide
Q2111674
diphenamid standard
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
diarylmethaneAny compound containing two aryl groups connected by a single C 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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency11.11020.001022.650876.6163AID1224838; AID1224839; AID1224893
progesterone receptorHomo sapiens (human)Potency43.23310.000417.946075.1148AID1346784; AID1347036
estrogen-related nuclear receptor alphaHomo sapiens (human)Potency54.42730.001530.607315,848.9004AID1224849
pregnane X nuclear receptorHomo sapiens (human)Potency19.31150.005428.02631,258.9301AID1346982
estrogen nuclear receptor alphaHomo sapiens (human)Potency53.65260.000229.305416,493.5996AID743079
peroxisome proliferator-activated receptor deltaHomo sapiens (human)Potency43.60380.001024.504861.6448AID743215
vitamin D (1,25- dihydroxyvitamin D3) receptorHomo sapiens (human)Potency0.48920.023723.228263.5986AID743222
nuclear factor erythroid 2-related factor 2 isoform 1Homo sapiens (human)Potency34.99170.000627.21521,122.0200AID743202; AID743219
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (35)

Assay IDTitleYearJournalArticle
AID1104609Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]malonate assessed as inhibition of [14C]-labeled 22C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104654Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]acetate assessed as [14C]-labeled 16C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 29.5 +/- 1.3%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104648Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]acetate assessed as [14C]-labeled 18C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 60.3 +/- 1.3%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104503Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]malonate assessed as inhibition of [14C]-labeled 18C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090120Growth inhibition of Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104600Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]malonate assessed as inhibition of [14C]-labeled 24C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090125Inhibition of Arbidopsis thaliana C-terminal His-tagged At1g04220 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104603Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]malonate assessed as inhibition of [14C]-labeled 24C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090128Inhibition of Arbidopsis thaliana C-terminal His-tagged KCS1 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104621Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]malonate assessed as inhibition of [14C]-labeled 16C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104500Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]malonate assessed as inhibition of [14C]-labeled 18C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104615Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]malonate assessed as inhibition of [14C]-labeled 20C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104642Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]acetate assessed as [14C]-labeled 20C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 4.7 +/- 1.6%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090124Inhibition of Arbidopsis thaliana C-terminal His-tagged At5g43760 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104618Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]malonate assessed as inhibition of [14C]-labeled 16C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090127Inhibition of Arbidopsis thaliana C-terminal His-tagged KCS2 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104660Inhibition of fatty acid synthesis in Hordeum vulgare (barley) assessed as inhibition of [14C]acetate incoporation in total fatty acids at 300 uM measured as total disintegration per g of fresh weight after 3 hr by liquid scintillation counting (Rvb = 5.72010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104630Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]acetate assessed as [14C]-labeled 24C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 6.5 +/- 1%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104636Inhibition of fatty acid synthesis in Hordeum vulgare (barley) using [14C]acetate assessed as [14C]-labeled 22C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 5.5 +/- 0.2%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090119Inhibition of Saccharomyces cerevisiae INVSc1 ELO at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104657Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) assessed as inhibition of [14C]acetate incoporation in total fatty acids at 300 uM measured as total disintegration per g of fresh weight after 3 hr by liquid scintillation counting (Rvb = 62010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104633Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]acetate assessed as [14C]-labeled 22C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 17.9 +/- 2.5%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104624Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) assessed as inhibition of [14C]malonate incoporation in total fatty acids at 300 uM measured after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104612Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]malonate assessed as inhibition of [14C]-labeled 20C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104606Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]malonate assessed as inhibition of [14C]-labeled 22C fatty acid production at 300 uM after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090129Inhibition of Arbidopsis thaliana C-terminal His-tagged FAE1 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104627Inhibition of fatty acid synthesis in Hordeum vulgare (barley) assessed as inhibition of [14C]malonate incoporation in total fatty acids at 300 uM measured after 3 hr by liquid scintillation counting2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090126Inhibition of Arbidopsis thaliana C-terminal His-tagged CER60 expressed in Saccharomyces cerevisiae INVSc1 at 100 uM after 18 to 20 hr by GC/MS analysis2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104645Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]acetate assessed as [14C]-labeled 18C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 41.2 +/- 1.1%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1090123Herbicidal activity against Arabidopsis thaliana assessed as apperance of fiddle head phenotype2004Proceedings of the National Academy of Sciences of the United States of America, Aug-10, Volume: 101, Issue:32
Specific and differential inhibition of very-long-chain fatty acid elongases from Arabidopsis thaliana by different herbicides.
AID1104651Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]acetate assessed as [14C]-labeled 16C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 29.2 +/- 3.5%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1104639Inhibition of fatty acid synthesis in Cucumis sativus (cucumber) using [14C]acetate assessed as [14C]-labeled 20C fatty acid level at 300 uM after 3 hr by liquid scintillation counting (Rvb = 5.1 +/- 0.7%)2010Pest management science, Jul, Volume: 66, Issue:7
The action of herbicides on fatty acid biosynthesis and elongation in barley and cucumber.
AID1159537qHTS screening for TAG (triacylglycerol) accumulators in algae2017Plant physiology, Aug, Volume: 174, Issue:4
Identification and Metabolite Profiling of Chemical Activators of Lipid Accumulation in Green Algae.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (11)

TimeframeStudies, This Drug (%)All Drugs %
pre-19902 (18.18)18.7374
1990's2 (18.18)18.2507
2000's2 (18.18)29.6817
2010's4 (36.36)24.3611
2020's1 (9.09)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.29

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 Index27.29 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.55 (4.65)
Search Engine Demand Index31.18 (26.88)
Search Engine Supply Index2.36 (0.95)

This Compound (27.29)

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]