131807-57-3 Usage
Trade name
DPX-JE874?; FAMOXATE?; MEDLEY?;
TANOS-50DF?
Pharmacology
Famoxadone inhibits activity of ubiquinol : cytochrome
c oxidoreductase at the Qo site of complex III,
the same target protein as the strobilurins (34,35). However,
studies show a difference in the potency of various
strobilurins compared with famoxadone in single amino
acid mutants of the cytochrome b protein, suggesting that
Famoxadone may interact differently with the target
protein (38).
Metabolic pathway
Famoxadone undergoes extensive degradation and metabolism in aqueous
and soil environments, in wheat plants, rats, goats and hens via common
pathways. The primary reactions include the hydrolytic opening of
the oxazolidinedione ring, aryl hydroxylation, cleavage of the phenoxyphenyl
and the oxazolidinedione-aminophenyl linkages and conjugation.
More than 25 degradation products have been identified.
Degradation
Famoxadone is relatively stable to hydrolytic degradation under dark
conditions in pH 5 buffer solution (DT50 41 days) (Jernberg et al., 1998a). It
was hydrolysed rapidly at pH 7 and pH 9 at 25 °C (DT50 values 2 days and
<2 hours, respectively). No sigruficant sunlight-induced degradation was
observed at pH 7. Hydrolytic degradation was catalysed in acidic conditions
(pH 5) under natural sunlight (DT50 4.6 days in contrast to 41 days at
pH 7). Primary hydrolytic degradation reactions include the opening
of the oxazolidinedione ring [to yieldα-hydroxy-α-methyl-4-phenoxyphenylacetic acid 2-phenylhydrazide (2) and 1-carboxy-1-(4-phenoxy-phenyl) ethyl-2-phenylhydrazinecarboxylic acid (3)], and the cleavage
of the oxazolidine-aminophenyl linkage to yield various products from
both the phenoxyphenyl moiety [ 1-(4-phenoxyphenyl)ethanone (4) and α-hydroxy-
α-methyl-4-phenoxyphenylacetiac acid (5)] and the aminophenyl moiety [small amounts of phenol (6), catechol (7) and benzene (8) via
the proposed 2-phenylhydrazinecarboxylic acid intermediate (9)] (see
Scheme 1).
Toxicity evaluation
Famoxadone has an acute oral LD50 > 5,000 mg/kg and
an acute percutaneous LD50 > 2,000 mg/kg in rats. It is
not a skin or eye irritant, is negative in the Ames test, and
is nonteratogenic. It shows very little soil degradation, is
nonmobile, and has a good ecotoxicological profile.
Check Digit Verification of cas no
The CAS Registry Mumber 131807-57-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,8,0 and 7 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 131807-57:
(8*1)+(7*3)+(6*1)+(5*8)+(4*0)+(3*7)+(2*5)+(1*7)=113
113 % 10 = 3
So 131807-57-3 is a valid CAS Registry Number.
InChI:InChI=1/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3
131807-57-3Relevant academic research and scientific papers
Synergistic Combinations Of Active Ingredients
-
, (2012/02/15)
The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and A have the meanings given in the description and, secondly, at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
Synergistic Active Compound Combinations Comprising Phenyltriazoles
-
, (2011/07/29)
The present invention relates to novel active compound combinations comprising, firstly, at least one known compound of the formula (I) in which R1 and R2 have the meanings given in the description. and at least one further known active compound from groups (2) to (27) listed in the description, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids and also phytopathogenic fungi.
Famoxadone: The discovery and optimisation of a new agricultural fungicide
Sternberg, Jeffrey A.,Geffken, Detlef,Adams Jr., John B.,Poestages, Reiner,Sternberg, Charlene G.,Campbell, Carlton L.,Moberg, William K.
, p. 143 - 152 (2007/10/03)
Famoxadone (3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione), is a new agricultural fungicide recently commercialized by DuPont under the trade name Famoxate. Famoxadone is a member of a new class of oxazolidinone fungicides th
Process for preparing fungicidal oxazolidinones and imidazolinones
-
, (2008/06/13)
The present invention pertains to a process for preparing compounds of Formula I (useful as fungicides and/or intermediates for producing fungicides) wherein Q is O or NH; W is O or S; X is H, halogen, C1-C4 alkyl, C1-Csu
Fungicidal mixtures
-
, (2008/06/13)
Advantageous combinations of an oxazolidinone and cymoxanil (or their agriculturally suitable salts) and their use to control fungus disease in plants are disclosed, the oxazolidinone having the formula STR1
Imidazole and triazole carboxylates, and processes for preparing 2,4-oxazolidinediones
-
, (2008/06/13)
Processes are described for preparing 2,4-oxazolidinediones having Formula (I) STR1 wherein: R1 is phenyl optionally substituted with 1-2 halogens; or 4-phenoxy, 4-(1-phenethyloxy) or 4-benzyloxy each optionally substituted with R2 o
Fungicidal oxazolidinones
-
, (2008/06/13)
Compounds for an methods of controlling plant diseases using thiooxazolidinones, oxazolidindiones and agriculturally suitable compositions containing them are disclosed.
