Dichlofluanid is a fungicide used to control a wide range of fungal diseases in various crops, including grapes, apples, and potatoes. It is a member of the anilide class of fungicides and is known for its broad-spectrum activity against Ascomycetes, Basidiomycetes, and Deuteromycetes fungi. Dichlofluanid is applied as a foliar spray and is effective in protecting plants from fungal infections, especially during the early stages of growth. The mechanism of action of dichlofluanid involves the inhibition of mitochondrial respiration in fungal cells, leading to their death. Its use is important due to its effectiveness against a wide range of fungal pathogens, its relatively low toxicity to mammals, and its ability to control diseases that can cause significant crop losses. However, dichlofluanid has been found to have some environmental impacts, including potential toxicity to aquatic organisms. Research on dichlofluanid focuses on understanding its environmental fate, its potential for resistance development, and its effects on non-target organisms. This research aims to ensure its safe and sustainable use in agriculture.'
dichlofluanid: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
dichlofluanid : A member of the class of sulfamides that is sulfamide in which the hydrogens attached to one of the nitrogens are replaced by methyl groups, while those attached to the other nitrogen are replaced by a phenyl and a [dichloro(fluoro)methyl]sulfanediyl group. A fungicide introduced in 1965 and used in the cultivation of fruit and vegetables, as well as in wood preservatives, it is no longer approved for use in the European Union. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 14145 |
| CHEMBL ID | 1269177 |
| CHEBI ID | 74875 |
| SCHEMBL ID | 20684 |
| MeSH ID | M0066308 |
| Synonym |
|---|
| n-(dichlor-fluor-methyl-thio)-n',n'-dimethyl-n-phenyl-schwefel-saeurediamid |
| bay 47531 |
| n,n-dimethyl-n'-phenyl-n'-[(fluorodichloromethyl)thio]sulfamide |
| eparen |
| wln: gxgfsnr&swn1&1 |
| 1,1-dichloro-n-[(dimethylamino)sulfonyl]-1-fluoro-n-phenylmethanesulfenamide |
| kue 13032c |
| bayer 47531 |
| oiparen |
| pecudin |
| dichlofluanid |
| euparene |
| n-dichloroacetyl-n-phenylsemicarbazide |
| elvaron |
| sulfamide,n'-dimethyl-n-phenyl- |
| n-[(dichlorofluoromethyl)thio]-n',n'-dimethyl-n-phenylsulfamide |
| methanesulfenamide,1-dichloro-n-[(dimethylamino)sulfonyl]-1-fluoro-n-phenyl- |
| ku 13-o32-c |
| 1085-98-9 |
| aniline, n-[(dichlorofluoromethyl)thio]-n-[(dimethylamino)sulfonyl]- |
| dichlofluanide |
| euparen |
| nsc218451 |
| nsc-218451 |
| methanesulfenamide, 1,1-dichloro-n-[(dimethylamino)sulfonyl]-1-fluoro-n-phenyl- |
| dichlofluanid [bsi:iso] |
| n-(dichlor-fluor-methyl-thio)-n',n'-dimethyl-n-phenyl-schwefel-saeurediamid [german] |
| n-dichlorfluormethylthio-n',n'-dimethylaminosulfonsaeureanilid [german] |
| dichlorfluanid |
| hsdb 1565 |
| sulfamide, n-((dichlorofluoromethyl)thio)-n',n'-dimethyl-n-phenyl- |
| n,n-dimethyl-n'-phenyl-n'-fluorodichloromethylthiosulfamide |
| 1,1-dichloro-n-((dimethylamino)sulfonyl)-1-fluoro-n-phenylmethanesulfenamide |
| nsc 218451 |
| n-dichlorofluoromethylthio-n',n'-dimethyl-n-phenylsulphamide |
| ccris 3647 |
| n-dichlorofluoromethanesulphenyl-n',n'-dimethyl-n-phenylsulphamide |
| diparen |
| epa pesticide chemical code 128844 |
| ku 13-032-c |
| dichlofluanide [iso-french] |
| brn 2947992 |
| 1,1-dichloro-n-((dimethylamino)sulfonyl)-1-fluoro-n-phenylmethane sulfenamide |
| aniline, n-((dichlorofluoromethyl)thio)-n-((dimethylamino)sulfonyl)- |
| dichlorfluanid [czech] |
| caswell no. 297a |
| n-(dichlorofluoromethylthio)-n',n'-dimethyl-n-phenylsulfamide |
| methanesulfenamide, 1,1-dichloro-n-((dimethylamino)sulfonyl)-1-fluoro-n-phenyl- |
| einecs 214-118-7 |
| n-(dichlorofluoromethylthio)-n-(dimethylsulfamoyl)-aniline |
| n-[dichloro(fluoro)methyl]sulfanyl-n-(dimethylsulfamoyl)aniline |
| inchi=1/c9h11cl2fn2o2s2/c1-13(2)18(15,16)14(17-9(10,11)12)8-6-4-3-5-7-8/h3-7h,1-2h3 |
| wurgxgvfsmyfcg-uhfffaoysa- |
| n-(dichloro-fluoromethyl)sulfanyl-n-(dimethylsulfamoyl)aniline |
| NCGC00248229-01 |
| C18820 |
| n-dichlorfluormethylthio-n',n'-dimethylaminosulfonsaeureanilid |
| unii-76a92xu36y |
| 76a92xu36y , |
| chebi:74875 , |
| CHEMBL1269177 |
| dtxsid5041851 , |
| dtxcid3021851 |
| cas-1085-98-9 |
| tox21_300960 |
| NCGC00254862-01 |
| FT-0603081 |
| n-{[dichloro(fluoro)methyl]sulfanyl}-n',n'-dimethyl-n-phenylsulfuric diamide |
| n-(dichlor-fluor-methyl-thio)-n',n'-dimethyl-n-phenylschwefel-saeurediamid |
| AKOS015888203 |
| dichlofluanid [iso] |
| bayer-47531 |
| n-dichlorofluoromethylthio-n',n'-dimethyl-n-phenylsulfamide |
| kue-13032c |
| dichlofluanid [hsdb] |
| dichlofluanid [mi] |
| n-((dichlorofluoromethyl)thio)-n',n'-dimethyl-n-phenylsulfamide |
| SCHEMBL20684 |
| WURGXGVFSMYFCG-UHFFFAOYSA-N |
| sulfamide, n-[(dichlorofluoromethyl)thio]-n',n'-dimethyl-n-phenyl- |
| n'-dichlorofluoromethylthio-nn-dimethyl-n'-phenylsulphamide |
| diclofluanide |
| n,n-dimethyl-n'-phenyl-n'-((fluorodichloromethyl)thio)sulfamide |
| n-([dichloro(fluoro)methyl]sulfanyl)-n',n'-dimethyl-n-phenylsulfamide # |
| J-002166 |
| dichlofluanid, pestanal(r), analytical standard |
| dichlofluanid 100 microg/ml in isooctane |
| Q421444 |
| AS-35177 |
| eparen; euparen; euparene |
| BCP28604 |
Dichlofluanid is a fungicide employed as a booster biocide in antifouling paints. Information its toxicity to aquatic organisms is scarce.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Dichlofluanid is a fungicide employed as a booster biocide in antifouling paints, but information its toxicity to aquatic organisms is scarce. " | ( Antifouling biocide dichlofluanid modulates the antioxidant defense system of the brown mussel Perna perna. da Rosa, CE; Gabe, H; Geihs, MA; Guerreiro, AS; Rola, RC; Sandrini, JZ, 2020) | 2.32 |
The EC10 and EC50 for chlorothalonil ranged from 2 to 108 and from 25 to 159 nM. Irgarol 1051 was the least toxic compound showing values from 3145 to >25600.
| Excerpt | Reference | Relevance |
|---|---|---|
| " The EC10 and EC50 for chlorothalonil ranged from 2 to 108 and from 25 to 159 nM; for Sea-Nine 211 values were 6-204 and 38-372 nM; for dichlofluanid effective concentrations were 95-830 and 244-4311 nM; tolylfluanid yielded values between 99-631 and 213-2839 nM; and Irgarol 1051 was the least toxic compound showing values from 3145 to >25600 and from 6076 to >25600 nM." | ( Comparative toxicity of alternative antifouling biocides on embryos and larvae of marine invertebrates. Bellas, J, 2006) | 0.54 |
| " The results of the toxicity experiments follow a normal distribution around the average value which allows to consider these values as reliable for comparison of the level of toxic effect detected with the two types of test containers." | ( A new simple method with high precision for determining the toxicity of antifouling paints on brine shrimp larvae (Artemia): first results. Bourdaniotis, N; Castritsi-Catharios, J; Persoone, G, 2007) | 0.34 |
| "Results obtained with the ANPP/CEB guideline allow the demonstration of significant differences between two slightly toxic products, a dichlofluanid 500 g kg(-1) kWP (Euparen) 50WP) and a quinoxyfen 250 g L(-1) SCC (Legend), and a highly toxic cymoxanil 60/mancozeb 200/folpet 275 g kg(-1) WP [Remiltine F Pepite) (RFP)], on the basis of bioassays conducted in the laboratory." | ( Suitability of two laboratory testing methods to evaluate the side effects of pesticides on Typhlodromus pyri Scheuten (Acari: Phytoseiidae). Auger, P; Bonafos, R; Guichou, S; Kreiter, S, 2008) | 0.55 |
| " Some are highly toxic to algae, including antifoulants, herbicides, and fungicides." | ( Mixture toxicity of five biocides with dissimilar modes of action on the growth and photosystem II efficiency of Chlamydomonas reinhardtii. de Almeida, ACG; Langford, K; Petersen, K; Thomas, KV; Tollefsen, KE, 2017) | 0.46 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "A method for rapid determination of dichlofluanid residue in vegetables using dispersive solid-phase extraction (dispersive-SPE) sample preparation combined with gas chromatography-mass spectrometry (GC-MS) was developed." | ( Rapid Determination of Dichlofluanid Residues in Vegetables Using Dispersive-SPE Sample Preparation Combined with Gas Chromatography-Mass Spectrometry. Cao, S; Chen, Z; Ding, X; Hu, J; Li, X; Xi, C; Xu, F; Zhou, X, ) | 0.72 |
| Role | Description |
|---|---|
| acaricide | A substance used to destroy pests of the subclass Acari (mites and ticks). |
| antifungal agrochemical | Any substance used in acriculture, horticulture, forestry, etc. for its fungicidal properties. |
| [role 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] | |
| Class | Description |
|---|---|
| sulfamides | Compounds where two amino groups are bound to an SO2 unit. |
| organofluorine compound | An organofluorine compound is a compound containing at least one carbon-fluorine bond. |
| organochlorine compound | An organochlorine compound is a compound containing at least one carbon-chlorine bond. |
| phenylsulfamide fungicide | An amide fungicide whose structure contains a phenylsulfamide moiety [ArN(R(1))SO2NR(2)R(3), where Ar represents phenyl or substituted phenyl]. |
| [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 | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Luciferase | Photinus pyralis (common eastern firefly) | Potency | 35.5742 | 0.0072 | 15.7588 | 89.3584 | AID1224835 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 56.6050 | 0.0025 | 41.7960 | 15,848.9004 | AID1347397; AID1347398; AID1347399 |
| hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 20.0510 | 3.1890 | 29.8841 | 59.4836 | AID1224846; AID1224894 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 5.1520 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| SMAD family member 2 | Homo sapiens (human) | Potency | 24.5412 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
| SMAD family member 3 | Homo sapiens (human) | Potency | 24.5412 | 0.1737 | 34.3047 | 61.8120 | AID1346924 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 2.3013 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 15.5268 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743035; AID743036; AID743042; AID743054; AID743063 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 9.2987 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377; AID1259378 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 32.9037 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| progesterone receptor | Homo sapiens (human) | Potency | 48.5577 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 17.7517 | 0.0002 | 14.3764 | 60.0339 | AID720691; AID720692 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 18.3441 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 14.2154 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 28.0566 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 12.2998 | 0.3758 | 27.4851 | 61.6524 | AID743217 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 54.4827 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 28.6861 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID743069; AID743075; AID743078; AID743079; AID743080; AID743091 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 4.1759 | 0.0010 | 24.5048 | 61.6448 | AID743212; AID743215 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 6.6965 | 0.0010 | 19.4141 | 70.9645 | AID743094; AID743140; AID743191 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 5.0389 | 0.0237 | 23.2282 | 63.5986 | AID743222; AID743223; AID743241 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 3.4376 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 35.9541 | 0.0016 | 28.0151 | 77.1139 | AID1224895; AID1259385; AID1259395 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 61.6448 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| thyrotropin-releasing hormone receptor | Homo sapiens (human) | Potency | 12.0019 | 0.1549 | 17.8702 | 43.6557 | AID1346877 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 13.8006 | 19.7391 | 45.9784 | 64.9432 | AID1159509 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 17.3739 | 0.0578 | 21.1097 | 61.2679 | AID1159526 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 1.2684 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 21.2130 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 14.9999 | 0.0006 | 27.2152 | 1,122.0200 | AID743202; AID743219 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 30.6379 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 39.2191 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID720552 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 30.6379 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 30.6379 | 0.0119 | 17.9420 | 71.5630 | AID651632 |
| Ataxin-2 | Homo sapiens (human) | Potency | 30.6379 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1102280 | Fungicidal activity against Blumeria graminis infected first-leaf stage of barley plant at 50 mg/l applied as spray under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| AID527529 | Fungistatic activity against Botrytis cinerea assessed as inhibition of fungal growth at 100 mg/L relative to control | 2010 | Bioorganic & medicinal chemistry letters, Nov-15, Volume: 20, Issue:22 | Metallocene catalyzed synthesis of fungistatic vicinal aminoalcohols under solvent free conditions. |
| AID1102285 | Fungicidal activity against Puccinia recondita infected first leaf stage of wheat plant at 50 mg/l applied as spray after 10 days under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| AID1102300 | Fungicidal activity against Rhizoctonia solani infected in third leaf stage of rice plant at 50 mg/l applied as spray after 5 days under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| AID1102295 | Fungicidal activity against Botryotinia fuckeliana infected first-leaf stage of cucumber plant at 50 mg/l applied as spray after 4 to 5 days under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| AID1102305 | Fungicidal activity against Magnaporthe grisea infected second leaf stage of rice plant at 50 mg/l applied as spray after 5 days under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| AID1102290 | Fungicidal activity against Phytophthora infestans infected second leaf-stage of tomato plant at 50 mg/l applied as spray after 4 days under green house conditions relative to control | 2003 | Journal of agricultural and food chemistry, Mar-12, Volume: 51, Issue:6 | Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 6 (11.32) | 18.7374 |
| 1990's | 6 (11.32) | 18.2507 |
| 2000's | 18 (33.96) | 29.6817 |
| 2010's | 20 (37.74) | 24.3611 |
| 2020's | 3 (5.66) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
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.
| This Compound (34.87) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 1 (1.82%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 54 (98.18%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||