Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-04-10
2001-06-05
Dees, Jose′ G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S222800, C514S223200, C514S223500
Reexamination Certificate
active
06242440
ABSTRACT:
CROSS REFERENCE TO RELATED APPLICATIONS
This application is the national stage of application no. PCT/EP98/06495, filed Oct. 7, 1998 which application claims priority from EP 97203227.0, filed Oct. 15, 1997.
This invention relates to synergistic compositions of oxathiazines and benzothiophene-2-carboxamide-S,S-dioxides for use as fungicidal preservatives in tie protection of materials, such as protection of wood, wood products, biodegradable materials and coatings.
It now has been found that compositions comprising particular ratios of an oxathiazine of formula (I) and a benzotihiophene-2-carboxamide-S,Sdioxide of formula (II) exhibit synergistic fungicidal activity.
The present invention is concerned with compositions comprising an oxathiazine of formula (I), or a salt thereof, and a benzothiophene-2-carboxamide-S,S-dioxide of formula (II), or a salt thereof, in quantities producing a mutual synergistic effect, and a carrier.
The oxathiazines of formula (I) have the following structure
wherein n is 0, 1 or 2; R
1
is hydrogen, C
1-4
alkyl or benzyl; and R
2
represents (a) phenyl; phenyl substituted with 1 to 3 substituents independently selected from hydroxyl, halo, C
1-12
alkyl, C
5-6
cycloaLkyl, trihalomethyl, phenyl, C
1-5
alkoxy, C
1-5
alkylthio, tetrahydropyranyloxy, phenoxy, C
1-5
alkycarbonyl, phenylcarbonyl, C
1-4
alkylsuifinyl, C
1-4
alkylsulfonyl, carboxy or its alkali metal salt, C
1-5
alkyloxy-carbonyl, C
1-5
alkylaminocarbonyl, phenylaminocarbonyl, tolylainocarbonyl, morpholinocarbonyl, amnino, nitro, cyano, dioxolanyl or C
1-4
alkyloxyiminomethyl; naphthyl; pyridinyl; thienyl, preferably when n is not 2; furanyl; or thienyl or furanyl substituted with one to three substituents independently selected from C
1-4
alkyl, C
1-4
alkyloxy, C
1-4
alkylthio, halo, cyano, formyl, acetyl, benzoyl, nitro, C
1-4
alkyloxy-carbonyl, phenyl, phenylaminocarbonyl and C
1-4
alkyloxyiminomethyl; or R
2
represents a radical of formula
wherein X is oxygen or suilfr; Y is nitrogen or CH or C(C
1-4
allyloxy); and R
3
is hydrogen or C
1-4
akyl.
Said compounds of formula (I) are described in WO-95/06043, published on Mar. 2, 1995, as a bactericidal and fungicidal compounds useful in wood-protection. The use of said compounds for the protection of non-living materials, in particular the anti-fouling use, is described in WO-95/05739, published on Mar. 2, 1995. WO95/05739 also describes the antibacterial, anti-yeast, antifungal, algicidal, anti-crustacean and molluscicidal properties of said compounds of formula (I) and compositions comprising them.
All compounds of formula (I) can be prepared following the procedures described in U.S. Pat. No. 4,569,690.
The benzothiophene-2-carboxamide-S,S-dioxides of formula (II) can be represented by the formula
wherein R
8
represents straight-chain or branched alkyl having 1 to 20 carbon atoms, or represents in each case straight-chain or branched halogenoalkyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl or alkoxycarbonylalkyl, each of which has 1 to 8 carbon atoms in the individual alkyl moieties, or represents straight-chain or branched alkenyl having 2 to 12 carbon atoms, or represents straight-chain or branched alkynyl having 2 to 12 carbon atoms, or represents cycloalkylalkyl or cycloalkyl, each of which has 3 to 7 carbon atoms in the cycloalkyl moiety and, in the case of cycloalkylalkyl, 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety, and each of which is optionally monosubstituted to hexasubstituted in the cycloalky moiety by identical or different substituents, suitable cycloalkyl substituents in each case being: halogen, in each case straight-chain or branched alkyl having 1 to 4 carbon atoms or in each case straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; furthermore represents arylalkyl, arylalkenyl, arylalyynyl or aryl, each of which has 6 or 10 carbon atoms in the aryl moiety and, in the cases of arylalkyl, arylalkenyl and arylalkynyl, up to 12 carbon atoms in the respective straight-chain or branched alkyl or alkenyl or alkynyl moiety, each of which is optionally monosubstituted to pentasubstituted in the aryl moiety by identical or different substituents, suitable aryl substituents in each case being: halogen, cyano, nitro, formylamido, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each of which has 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkylcarbonyl, alkoxycarbonyl, aminocarbonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl, alkylcarbonylamino, N-alkyl-alkylcarbonylamino, N-alkylformyl-carbonylamino or alkoximinoalkyl, each of which has 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally monosubstituted or polysubstituted by identical or different substituents from the group consisting of halogen and/or straight-chain or branched aLkyl having 1 to 4 carbon atoms; R
9
represents hydrogen or straight-chain or branched alkyl which has 1 to 6 carbon atoms and which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents being: hydroxyl, halogen, cyano, and in each case straight-chain or branched alkoxy, alkoxycarbonyl or dialkylamino; each of which has 1 to 6 carbon atoms in the individual akyl moieties; or R
8
and R
9
together with the nitrogen atom to which they are bonded represent a saturated 5- to 7-membered heterocycle which is optionally monosubstituted or polysubstituted by identical or different substituents and which can optionally contain 1 or 2 further hetero atoms selected from the group consisting of nitrogen, oxygen and sulphur, suitable substituents in each case being: halogen, in each case straight-chain or branched alkyl, alkoxy or alkoxycarbonyl having in each case 1 to 4 carbon atoms or straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms; and
R
4
, R
5
, R
6
and R
7
independently of one another in each case represent hydrogen, halogen, cyano, nitro or in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio each of which has 1 to 6 carbon atoms and, in the case of halogenoaLky, halogenoalkoxy or halogenoalkylthio, 1 to 13 identical or different halogen atoms.
Said compounds of formula (II), their preparation and use in plant protection, the protection of materials and in the field of human and veterinary medicine, are described in EP-0,512,349, published on Nov. 11, 1992.
All compounds of formula (II) can be prepared following the procedures described in EP-0,512,349.
In the foregoing definitions halo is generic to fluoro, chloro, bromo and iodo; C
1-4
alkyl defines straight and branch chained saturated hydrocarbon radicals having from 1 to 4 carbon atoms comprising methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1,1-dimethyl-ethyl, 1-methylpropyl, 2-methylpropyl; C
1-5
alkyl includes C
1-4
alkyl radicals as defined above and saturated hydrocarbon radicals having five carbon atoms, e.g. n-pentyl and the branched pentyl isomers; C
1-6
alkyl includes C
1-5
alkyl radicals as defined above and six carbon containing homologues, e.g. n-hexyl and the branched hexyl isomers; C
1-12
alkyl includes C
1-6
alkyl and saturated hydrocarbon radicals having from 7 to 12 carbon atoms, e.g. heptyl, octyl, nonyl, decyl, undecyl and their isomers. The term alkali metal cation in particular is a sodiurm or potassium cation. Trihalomethyl defines a methyl group being fully substituted with halo atoms, in particular trifluoromethyl and trichloromethyl. C
1-4
alkyloxyiminomethyl defines a radical of formula —CH═N—O—C
1-4
alkyl. C
5-6
cycloalkyl comprises cyclopentyl and cyclohexyl.
Particular compounds of formula (I) for use in the method are those wherein n is 0, 1 or 2; R
1
is hydrogen, C
1-4
alkyl or benzyl; an
De Witte Ludo Antoinnette
Valcke Alex Raymond Albert
Van Der Flaas Mark Arthur Josepha
Willems Willy Modest Louisa
Dees Jose′ G.
Janssen Pharmaceutica N.V.
Pryor Alton
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