Compositions: coating or plastic – Coating or plastic compositions – Contains fireproofing or biocidal agent
Reexamination Certificate
1998-03-11
2001-04-17
Green, Anthony (Department: 1755)
Compositions: coating or plastic
Coating or plastic compositions
Contains fireproofing or biocidal agent
C424S405000, C424S078090, C504S154000, C514S378000, C514S443000, C548S240000, C548S525000, C549S053000, C549S055000, C549S057000
Reexamination Certificate
active
06217642
ABSTRACT:
This application is a 371 of PCT/EP96/03941, which was filed on Sep. 9, 1996.
The present invention relates to a method and composition for protecting objects from fouling, in particular ships' hulls, screens, nets, structures, wharfs and signalling installations, which come into contact with sea-water or brackish water.
Fouling by species of the group Lepadomorpha (goose barnacles), such as various Lepas and Scalpellum species, or by species of the group Balanomorpha (acorn bamacles), such as Balanus or Pollicipes species, increases the frictional resistance of ships and as a result, due to increased consumption of energy and frequent periods in dry dock, leads to a significant increase in operating costs.
In addition to fouling by algae, for example Ectocarpus sp. and Ceramium sp., fouling by sessile Entomossra groups, called collectively by the name Cirripedia (barnacle crabs) is of special importance in particular.
Benzothiophene-2-carboxamide S,S-dioxides (BCDs), a process for their preparation and their fungicidal action are known (DE-A41 15 184). Their activity against phytopathogenic fungi and dermatophytes is described in particular. It is furthermore stated that BCDs are suitable for protection of industrial materials against microbial change or destruction.
Their use for treatment of mould-resistant emulsion paints is known from U.S. Pat. No. 5,622,546, equivalented to EP 714420.
It has now been found, surprisingly, that BCDs not only attack the species of moulds which usually grow on paints, but also have an outstanding antifouling action.
The application therefore relates to the use of benzothiophene-2-carboxamide S,S-dioxides for protection of objects against fouling.
The compounds used as antifouling active compounds in this invention are represented by the formula (I)
in which
R
1
represents optionally substituted alkyl, or represents alkenyl or alkinyl, or represents in each case optionally substituted cycloalkyl or cycloalkylalkyl, or represents in each case optionally substituted aralkyl, aralkenyl, aralkinyl or aryl,
R
2
represents hydrogen, or represents optionally substituted alkyl, or
R
1
and R
2
, together with the nitrogen atom to which they are bonded, represent an optionally substituted heterocyclic radical and
R
3
, R
4
, R
5
and R
6
independently of one another each represent hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy or halogenoalkylthio.
Compounds of the formula (I) which are preferably used are those in which
R
1
represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or i-octyl, n- or i-nonyl, n- or i-decyl, n- or i-dodecyl or n- or i-octadecyl, or represents allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butinyl, n- or i-pentinyl, n- or i-hexinyl, chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl, cyanomethyl, cyanoethyl, cyanopropyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, ethoxycarbonylpropyl, propoxycarbonylmethyl, propoxycarbonylethyl or propoxycarbonylpropyl; or further represents cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclopentyl, cyclopentylmethyl, cyclopentylethyl, cyclpentylpropyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl or cyclohexylpropyl, in each case optionally substituted in the cycloalkyl part once to four times in an identical or different manner by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl or trifluoromethyl; or furthermore represents phenylalkyl, phenylalkenyl, phenylalkinyl, phenyl or naphthyl, in each case optionally substituted in the aryl part once to three times in an identical or different manner and in each case, where appropriate, having up to 6 carbon atomns in the straight-chain or branched alkyl or alkenyl or alkinyl part, possible substituents on the aryl in each case being: fluorine, chlorine, bromine, hydroxy, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, tifluoromethoxy, trifluoromethylthio, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, aminocarbonyl, N-methylaminocarbonyl, N,N-dimethylaminocarbonyl, N-ethylaminocrbonyl, N,N-diethylaminocarbonyl, N-formylamino, N-acetylamino, N-methyl-N-formylamino, N-methyl-N-acetyl-amino, N-ethyl-N-formylamino, N-ethyl-N-acetyl-amino, methoximinomethyl, methoximinoethyl, ethoximinomethyl, ethoximinoethyl or phenyl which is optionally substituted once to three times in an identical or different manner by fluorine, chlorine, bromine, methyl and/or ethyl,
R
2
represents hydroge, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl, cyanomethyl, cyanoethyl, cyanopropyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, methoxycarbonylmethyl, methoxycarbonylethyl, methoxycarbonylpropyl, ethoxycarbonylmethyl, ethoxycarbonylethyl, ethoxycarbonylpropyl, propoxycarbonylmethyl, propoxycarbonylethyl, propoxycarbonylpropyl, dimethylaminomethyl, diethylaminomethyl, dipropylaminomethyl, dimethylaminoethyl, diethylaminoethyl, dipropylaminoethyl, dimethylaminopropyl, diethylaminopropyl or dipropylaminopropyl or
R
1
and R
2
, together with the nitrogen atom to which they are bonded, represent a heterocyclic radical of the formula
which is optionally substituted once, twice or three times by methyl and/or ethyl, and
R
3
, R
4
, R
5
and R
6
independently of one another each represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio.
Compounds of the formula (I) which are particularly preferably used are those in which
R
1
represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n- or i-pentyl, n- or i-hexyl, n- or i-heptyl, n- or ioctyl, n- or i-nonyl, n- or i-ecyl, n- or i-dodecyl, n- or i-octadecyl, or represents allyl, n- or i-butenyl, n- or i-pentenyl, n- or i-hexenyl, propargyl, n- or i-butinyl, n- or i-pentinyl, n- or i-hexinyl, chloromethyl, bromomethyl, chloroethyl, bromoethyl, chloropropyl, bromopropyl, cyanomethyl, cyanoethyl, cyanopropyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, or furthermore represents cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclopropylpropyl, cyclopentyl, cyclopentylmethyl, cyclopentylethyl, cyclopentylpropyl, cyclohexyl, cyclohexylmethyl, cyclohexylethyl or cyclohexylpropyl, in each case optionally substituted in the cycloalkyl part once to four times in an identical or different manner by fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, chloromethyl, dichloromethyl or trifluoromethyl; or furthermore represents phenylalkyl, phenylalkenyl, phenylaikinyl, phenyl or naphthyl, in each case optionally substituted in the aryl part once to three times in an identical or different manner and in each case, where appropriate, having up to 6 carbon atoms in the straight-chain or branched alkyl or alkenyl or alkinyl part, possible substituents on the aryl in each case being: fluorine, chlorine, bromine, hydroxy, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylcarbonyl, ethylcarbonyl, methoxycarbonyl, ethoxycarbonyl, or phenyl which is optionally substituted once to three times in an ident
Elbe Hans-Ludwig
Kugler Martin
Kunisch Franz
Schrage Heinrich
Bayer Aktiengesellschaft
Green Anthony
Norris & McLaughlin & Marcus
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