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US 5,855,654 AGranted
Pyridazinones as marine antifouling agents
AssigneeRohm and Haas Company
InventorsGary Lewis Willingham, Samuel Eugene Sherba, Barry Clifford Lange, Enrique Luis Michelotti
Life of this patent
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Abstract
Disclosed is a method of inhibiting the growth of marine organisms on a marine structure, by applying dihydropyridazinone and pyridazinone compounds onto or into the marine structure. These compounds may be directly incorporated into the marine structure during manufacture, directly applied to the structure, or applied to the structure by means of a coating.
Claims7
A method of inhibiting the growth of marine organisms on a marine structure, comprising applying to, on, or in the marine structure a marine organism inhibiting amount of a marine antifouling agent of formula:
- ##STR6## wherein:
- A=--(CHR.sup.2).sub.n --CHR.sup.7 --Z;
- --CR.sup.2 .dbd.CR.sup.7 --Z--;
- CHR.sup.2 --CR.sup.7 .dbd.X--;
- or --CR.sup.2 .dbd.CR.sup.2 --X--;
- D=nitrogen;
- Q=an aromatic group selected from ##STR7## Z=a carbonyl or thiocarbonyl;
- X=a carbon substituted by halo, alkoxy, alkynylthio, or triazolyl;
- R.sup.1 =(C.sub.3 -C.sub.10)alkynyl, (C.sub.4 -C.sub.20)dialkynyl, halo(C.sub.3 -C.sub.6)alkynyl, phenyl(C.sub.3 -C.sub.6)alkynyl, heterocyclyl(C.sub.3 -C.sub.6)alkynyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.3 -C.sub.6)alkynyl, (C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl, hydroxy(C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkanoyloxy(C.sub.3 -C.sub.6)alkynyl, formyl(C.sub.3 -C.sub.6)alkynyl, tri(C.sub.1 -C.sub.6)alkylsilyl(C.sub.3 -C.sub.6)alkynyl, halo(C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl, carboxy(C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.3 -C.sub.6)alkynyl;
- R.sup.2 =hydrogen, (C.sub.1 -C.sub.3)alkyl, phenyl, or halogen;
- R.sup.3 and R.sup.6 are independently hydrogen, (C.sub.1 --C.sub.6)alkoxy, or halogen;
- R.sup.2 and R.sup.3 may together form a (C.sub.1 -C.sub.3)alkyl;
- R.sup.4 =hydrogen, halogen, (C.sub.1 -C.sub.6)alkoxy, or nitro;
- R.sup.5 =hydrogen, halogen, nitro, (C.sub.1 -C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkoxy, halo(C.sub.1 -C.sub.6)alkylthio, phenyl, phenoxy, or cyano;
- R.sup.7 =hydrogen, (C.sub.1 -C.sub.3)alkyl, phenyl, halogen, (C.sub.3 -C.sub.6)alkynyl(C.sub.2 -C.sub.6)alkenyl, (C.sub.3 -C.sub.10)alkynyl, (C.sub.4 -C.sub.20)dialkynyl, halo(C.sub.3 -C.sub.6)alkynyl, or (C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl;
- R.sup.2 and R.sup.7 may together form a fused phenyl ring;
- and
- n=1.
15 more elements
A method of inhibiting the growth of marine organisms on a marine structure comprising applying to, on or in the marine structure a marine organism inhibiting amount of a combination of a first marine antifouling agent of the formula ##STR8## wherein:
- A=--(CHR.sup.2).sub.n --CHR.sup.7 --Z;
- --CR.sup.2 .dbd.CR.sup.7 --Z--;
- CHR.sup.2 --CR.sup.7 .dbd.X--;
- or --CR.sup.2 .dbd.CR.sup.2 --X--;
- D=nitrogen,
- Q=an aromatic group selected from ##STR9## Z=a carbonyl or thiocarbonyl;
- X=a carbon substituted by halo, alkoxy, alkynylthio, or triazolyl;
- R.sup.1 =(C.sub.3 -C.sub.10)alkynyl, (C.sub.4 -C.sub.20)dialkynyl, halo(C.sub.3 -C.sub.6)alkynyl, phenyl(C.sub.3 -C.sub.6)alkynyl, heterocyclyl(C.sub.3 -C.sub.6)alkynyl, (C.sub.3 -C.sub.6)cycloalkyl(C.sub.3 -C.sub.6)alkynyl, (C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl, hydroxy(C.sub.3 -C.sub.6)alknyl, (C.sub.1 -C.sub.6)alkoxy(C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkanoyloxy(C.sub.3 -C.sub.6)alkynyl, formyl(C.sub.3 -C.sub.6)alkynyl, tri(C.sub.1 -C.sub.6)alkylsilyl(C.sub.3 -C.sub.6)alkynyl, halo(C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl, carboxy(C.sub.3 -C.sub.6)alkynyl, (C.sub.1 -C.sub.6)alkoxycarbonyl(C.sub.3 -C.sub.6)alkynyl;
- R.sup.2 =hydrogen, (C.sub.1 -C.sub.3)alkyl, phenyl, or halogen;
- R.sup.3 and R.sup.6 are independently hydrogen, (C.sub.1 -C.sub.6)alkoxy, or halogen;
- R.sup.2 and R.sup.3 may together form a (C.sub.1 -C.sub.3)alkyl;
- R.sup.4 =hydrogen, halogen, (C.sub.1 -C.sub.6)alkoxy, or nitro;
- R.sup.5 =hydrogen, halogen, nitro, (C.sub.1 --C.sub.6)alkyl, (C.sub.1 -C.sub.6)alkoxy, (C.sub.1 -C.sub.6)alkylthio, halo(C.sub.1 -C.sub.6)alkyl, halo(C.sub.1 -C.sub.6)alkoxy, halo(C.sub.1 -C.sub.6)alkylthio, phenyl, phenoxy, or cyano;
- R.sup.7 =hydrogen, (C.sub.1 -C.sub.3)alkyl, phenyl, halogen, (C.sub.3 -C.sub.6)alkynyl(C.sub.2 -C.sub.6)alkenyl, (C.sub.3 -C.sub.10)alkynyl, (C.sub.4 -C.sub.20)dialkynyl, halo(C.sub.3 -C.sub.6)alkynyl, or (C.sub.3 -C.sub.6)alkenyl(C.sub.3 -C.sub.6)alkynyl;
- R.sup.2 and R.sup.7 may together form a fused phenyl ring;
- n=1;
- and a second marine antifouling agent selected from the group consisting of:
- tin based marine antifoulants;
- manganese ethylenebisdithiocarbamate;
- zinc dimethyl dithiocarbamate;
- 2-methyl-4-t-butylamino-6-cyclopropylamino-s-triazine;
- 2,4,5,6-tetrachloroisophthalonitrile;
- N,N-dimethyl dichlorophenyl urea;
- zinc ethylenebisdithiocarbamate;
- copper thiocyanate;
- 4,5-dichloro-2-n-octyl-3-isothiazolone;
- N-(fluorodichloromethylthio)-phthalimide;
- N,N-dimethyl-N'-phenyl-N'-fluorodichloromethylthio-sulfamide;
- zinc 2-pyridinethiol-1-oxide;
- tetramethylthiuram disulfide;
- copper-10% nickel alloy solid solution;
- 2,4,6-trichlorophenylmaleimide;
- 2,3,5,6-tetrachloro-4-(methylsulfonyl)-pyridine;
- 3-iodo-2-propynyl butyl carbamate;
- diiodomethyl p-tolyl sulfone;
- bis dimethyl dithiocarbamoyl zinc ethylenebisdithiocarbamate;
- phenyl (bispyridil) bismuth dichloride;
- 2-(4-thiazolyl)-benzimidazole;
- pyridine triphenyl borane;
- and 2-haloalkoxyaryl-3-isothiazolones;
- wherein the ratio of the first marine antifouling agent to the second marine antifouling agent is from 99:1 to 1:99.
38 more elements
Dependencies are inferred from the claim text.