Controlled release compositions

Details Controlled release compositions Controlled release compositions

1998-05-06

2001-04-24

Levy, Neil S. (Department: 1616)

Drug, bio-affecting and body treating compositions

Preparations characterized by special physical form

Biocides; animal or insect repellents or attractants

C424S406000, C424S407000, C424S411000, C514S372000, C514S731000, C514S734000

Reexamination Certificate

active

06221374

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates generally to a composition for controlling the release of biologically active compounds. In particular, this invention relates to the use of certain polyphenolic compounds to control the release of biologically active compounds.
The ability to control release of biologically active compounds to a locus to be protected is important in the field of biologically active compounds. Typically, when a biologically active compound is added to a locus to be protected, the compound is rapidly released, whether or not it is needed. Controlled release compositions deliver the biologically active compound in a manner that more closely matches the need for the compound. In this way, only the amount of the biologically active compound needed is released into the locus to be protected. Controlled release offers the advantages of reduced cost, lowered toxicity and increased efficiency.
Various methods of controlled release are known. Such methods include encapsulation of the biologically active compound, adsorption of the biologically active compound on an inert carrier, such as silica gel, and clathration of the biologically active compound.
All of these methods have drawbacks to widespread commercial use, such as expensive starting materials, limited compatibility of the controlled release method to the compounds to be released or locus to be protected, and limited control of the release of the biologically active compounds. For example, whether a clathrate forms is solvent dependent, which limits available solvent choices. An additional problem with clathrates is that solvent, rather than the desired biologically active compound, is sometimes incorporated into the complex.
For example, EP 709 358 A (Suzuki et al.) discloses a clathrate of isothiazolones using a tetrakisphenol compound. Although these compositions provide some control of the release of the isothiazolone, the amount of control is limited and the tetrakisphenol compound used to prepare the clathrate is very expensive. Suzuki et al. do not discuss polyphenolic compounds other than tetrakisphenols.
JP 07 003 191 A, assigned to Kurita, discloses a clathrate of isothiazolones with 5,5′-dichloro-2,2′-dihydroxydiphenylmethane for use in marine antifouling paints. These compositions have achieved limited success because 5,5′-dichloro-2,2′-dihydroxydiphenylmethane is banned in some countries.
There is therefore a continuing need for controlled release biologically active compositions that are inexpensive, compatible in a broad range of loci to be protected, and more effective at controlling the release of the biologically active compound than compositions currently available.
SUMMARY OF THE INVENTION
The present invention is directed to a controlled release composition comprising a biologically active compound and a polyphenolic compound of the formula
wherein A=CR
4
R
5
, dicyclopentadiene; R
1
=H, (C
1
-C
8
)alkyl; R
2
, R
3
, R
4
, R
5
, R
6
are independently selected from R
1
, OR
1
, SR
1
, NO
2
, CN, CO
2
R
1
, halo, phenyl, substituted phenyl, phenoxy, substituted phenoxy, (C
1
-C
4
)alkoxyphenyl, substituted (C
1
-C
4
)alkoxyphenyl; m=0 or 1; n=0-100; provided that when m=0 n=0; and wherein the polyphenolic compound is optionally crosslinked.
The present invention is also directed to a method of controlling or inhibiting the growth of microorganisms in a locus comprising introducing into or onto the locus to be protected an effective amount of the composition described above.
The present invention is further directed to a method of eliminating or inhibiting the growth of marine organisms on a structure comprising introducing into or onto the structure to be protected an effective amount of the composition described above.
The present invention is further directed to a method of eliminating or inhibiting the growth of fungi, plants and insects comprising introducing into or onto the locus to be protected an effective amount of the composition described above.
DETAILED DESCRIPTION OF THE INVENTION
As used throughout the specification, the following terms shall have the following meanings, unless the context clearly indicates otherwise.
The term “biologically active compounds” refers to microbicides, marine antifouling agents, and agricultural pesticides. “Microbicide” refers to a compound capable of inhibiting the growth of or controlling the growth of microorganisms at a locus. The term “microorganism” includes, but is not limited to, fungi, bacteria, and algae.
“Marine antifouling agent” includes algaecides and molluscicides. “Marine antifouling activity” is intended to include both the elimination of and inhibition of growth of marine organisms. Marine organisms controlled by marine antifouling agents suitable for use in this invention include both hard and soft fouling organisms. Generally speaking, the term “soft fouling organisms” refers to plants and invertebrates, such as slime, algae, kelp, soft corals, tunicates, hydroids, sponges, and anemones, while the term “hard fouling organisms” refers to invertebrates having some type of hard outer shell, such as barnacles, tubeworms, and molluscs.
“Agricultural pesticides” include agricultural fungicides, herbicides and insecticides. “Agricultural fungicide” refers to a compound capable of inhibiting the growth of or controlling the growth of fungi in an agricultural application, such as treatment of plants and soil; “herbicide” refers to a compound capable of inhibiting the growth of or controlling the growth of certain plants; and “insecticide” refers to a compound capable of controlling insects.
“Alkyl” means straight chain, branched, cyclic, or any combination thereof; “halogen” and “halo” mean fluorine, chlorine, bromine, or iodine. “Substituted phenyl,” “substituted phenoxy” and “substituted (C
1
-C
4
)alkoxyphenyl” mean one or more of the hydrogens on the aromatic ring are replaced by another substituent, such as cyano, hydroxy, (C
1
-C4)alkyl, nitro, mercapto, (C
1
-C
4
)alkylthio, halo and (C
1
-C4)alkoxy. All amounts are percent by weight (“%wt”), unless otherwise noted and all %wt ranges are inclusive. As used throughout the specification, the following abbreviations are applied: g=gram; mg=microgram; mL=milliliter; MW=molecular weight; IR=infrared; rpm=revolutions per minute; HPLC=high performance liquid chromatography; ppm=parts per million; and AWPA=American Wood Preservers Association.
The biologically active compounds useful in this invention are those which are hydrogen bond acceptors. That is, the compounds are those having one or more atoms selected from nitrogen, oxygen, fluorine or mixtures thereof. The nitrogen or oxygen may have single or multiple bonds, such as in a carbonyl, imine, nitrile, hydroxy, amide, alkoxy, ester, ether or amine group.
Suitable microbicides of the present invention include, but are not limited to: 5-chloro-2-methyl-3-isothiazolone; 2-methyl-3-isothiazolone; 2-n-octyl-3-isothiazolone; 4,5-dichloro-2-n-octyl-3-isothiazolone; 3-iodo-2-propynyl butyl carbamate; 1,2-dibromo-2,4-dicyanobutane; methylene-bis-thiocyanate; 2-thiocyanomethylthiobenzothiazole; tetrachloroisophthalonitrile; 5-bromo-5-nitro-1,3-dioxane; 2-bromo-2-nitopropanediol; 2,2-dibromo-3-nitrilopropionamide; N,N′-dimethylhydroxyl-5, 5′- dimethylhydantoin; bromochlorodimethylhydantoin; 1,2-benzisothiazolin-3-one; 4,5-trimethylene-2-methyl-3-isothiazolone; 5-chloro-2-(2,4-dichlorophenoxy)phenol and 3,4,4′-trichlorocarbanilide.
Suitable marine antifouling agents of the present invention include, but are not limited to: 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&p

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