Alkynyl aryl sulfones

Details Alkynyl aryl sulfones Alkynyl aryl sulfones

1999-09-21

2001-05-15

Vollano, Jean F (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Sulfur containing

C568S030000, C568S031000, C568S029000, C568S033000

Reexamination Certificate

active

06232503

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to alkynyl aryl sulfones and the use of such compounds as biocides.
BACKGROUND OF THE INVENTION
Aryl sulfones are known to be effective as herbicides and plant growth regulators. See, for example, U.S. Pat. Nos. 4,335,142; 4,559,082; and 3,267,150.
Moore et al., U.S. Pat. No. 3,267,150, discloses halo-alkenyl sulfones useful as agricultural products, such as germicides and fungicides.
Felix et al., U.S. Pat. No. 4,559,082, describes herbicidal compositions comprising an herbicidally effective amount of a thiocarbamate and an amount of an unsaturated aryl sulfide, sulfoxide, or sulfone sufficient to extend the soil life of the thiocarbamate.
Although there are numerous biocidal compositions on the market, there is a continuing need for neutral compositions with high biocidal efficacy.
SUMMARY OF THE INVENTION
Applicants have discovered alkynyl aryl sulfones having high biocidal activity. These compounds are useful as biocides, including, but not limited to, bactericides, fungicides, and preservatives. Applicants have also discovered that haloalkynyl aryl sulfones may be prepared by reacting the corresponding non-halogenated alkynyl aryl sulfone with N-iodosuccinamide or N-bromosuccinamide, acetone, and silver nitrate.
Biocidal compositions comprising a microbiocidally effective amount of one or more of the alkynyl aryl sulfones are a further embodiment of the present invention.
Still another embodiment is a method of controlling microorganisms comprising applying an effective amount of one or more alkynyl aryl sulfones to the microorganisms.
DETAILED DESCRIPTION OF THE INVENTION
The present invention encompasses halogenated alkynyl aryl sulfones having formula I below:
where R
1
, R
2
, R
3
, R
4
, and R
5
are independently hydrogen, chlorine, bromine, fluorine, iodine, substituted or unsubstituted linear or branched C
1
-C
3
alkoxy, substituted or unsubstituted linear or branched C
1
-C
3
thioalkoxy, substituted or unsubstituted linear or branched C
1
-C
8
alkyl, hydroxyl, thiol, —CN, —CF
3
, —OCF
3
, —NO
2
, acetyl, or —NR
6
R
7
; R
6
and R
7
are independently hydrogen, methyl, or ethyl; and X is iodine or bromine. R
1
and R
2
are preferably hydrogen. Preferably, at least two of R
3
, R
4
, and R
5
are hydrogen and X is iodine. More preferably, two of R
3
, R
4
, and R
5
are hydrogen and the third group is hydrogen, chlorine, bromine, fluorine, iodine, methyl, ethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, thiomethoxy, thioethoxy, n-thiopropoxy, iso-thiopropoxy, linear or branched C
1
,-C
8
alkyl, —CF
3
, or—NO
2
. Most preferably, two of R
3
, R
4
, and R
5
are hydrogen and the third group is hydrogen, chlorine, bromine, fluorine, iodine, methyl, ethyl, methoxy, ethoxy, n-propoxy, or iso-propoxy.
Examples of preferred compounds of formula I include, but are not limited to, iodoethynyl 4-methylbenzene sulfone; iodoethynyl 4-methoxybenzene sulfone; iodoethynyl 4-thiomethoxybenzene sulfone; iodoethynyl 4-t-butylbenzene sulfone; iodoethynyl 4-ethylbenzene sulfone; iodoethynyl 4-trifluoromethoxybenzene sulfone; iodoethynyl 2,4,6-trimethylbezene sulfone; iodoethynyl 3,4-dimethoxybenzene sulfone; and iodoethynyl benzene sulfone. Examples of more preferred compounds of formula I include, but are not limited to, iodoethynyl 4-methylbenzene sulfone, iodoethynyl 4-ethylbenzene sulfone, and iodoethynyl 4-methoxybenzene sulfone.
Another embodiment of the present invention encompasses alkynyl aryl sulfones having formula II below:
where R
8
, R
9
, R
10
, R
11
, and R
12
are independently hydrogen, chlorine, bromine, fluorine, iodine, substituted or unsubstituted linear or branched C
1
-C
3
alkoxy, substituted or unsubstituted linear or branched C
1
-C
3
thioalkoxy, substituted or unsubstituted linear or branched C
1
-C
8
alkyl, hydroxyl, thiol, —CN, —CF
3
, —OCF
3
, —NO
2
, acetyl, or —NR
13
R
14
; R
13
and R
14
are independently hydrogen, methyl, or ethyl; and at least one of R
8
, R
9
, R
10
, R
11
, and R
12
is not hydrogen or methyl; with the proviso that R
10
is fluorine, iodine, ethoxy, substituted or unsubstituted n-propoxy, substituted or unsubstituted iso-propoxy, substituted or unsubstituted linear or branched C
1
-C
3
thioalkoxy, substituted or unsubstituted ethyl, substituted or unsubstituted linear or branched C
3
-C
8
, alkyl, hydroxyl, thiol, —CN, —CF
3
, —OCF
3
, acetyl, or —NR
13
R
14
when R
8
, R
9
, R
11
, and R
12
are hydrogen. R
8
and R
9
are preferably hydrogen. When R
8
, R
9
, and R
10
are hydrogen, preferably, one of R
11
and R
12
is hydrogen and the other is chlorine, bromine, fluorine, iodine, methoxy, ethoxy, n-propoxy, iso-propoxy, thiomethoxy, thioethoxy, n-thiopropoxy, or iso-thiopropoxy. When R
8
, R
9
, R
11
, and R
12
are hydrogen, R
10
is preferably fluorine, iodine, ethoxy, n-propoxy, iso-propoxy, thiomethoxy, thioethoxy, n-thiopropoxy, or iso-thiopropoxy.
Examples of preferred compounds of formula II include, but are not limited to, ethynyl 4-t-butylbenzene sulfone; ethynyl 4-thiomethoxybenzene sulfone; ethynyl 4-ethylbenzene sulfone; ethynyl 4-trifluoromethoxybenzene sulfone; and ethynyl 3,4-dimethoxybenzene sulfone.
The invention also encompasses alkynyl aryl sulfones having formula III below:
wherein R
8
, R
9
, R
10
, R
12
, and R
11
are independently hydrogen or methyl and at least two of R
8
, R
9
, R
10
, R
11
, and R
12
are methyl; with the proviso that R
8
is not methyl when R
9
and R
11
are hydrogen and R
10
and R
12
are methyl.
Another embodiment of the invention is a biocidal concentrate comprising from about 1 to about 15%, preferably from about 1 to about 5%, by weight of one or more alkynyl aryl sulfones having the formula
where R
15
, R
16
, R
17
, R
18
, and R
19
are independently hydrogen, chlorine, bromine, fluorine, iodine, substituted or unsubstituted linear or branched C
1
-C
3
alkoxy, substituted or unsubstituted linear or branched C
1
-C
3
thioalkoxy, substituted or unsubstituted linear or branched C
1
-C
8
alkyl, hydroxyl, thiol, —CN, —CF
3
, —OCF
3
, —NO
2
, acetyl, or —NR
20
R
21
; R
20
and R
21
are independently hydrogen, methyl, or ethyl; and X is hydrogen, iodine, or bromine, based upon 100% weight of total concentrate. The compounds of formula IV include, but are not limited to, the aforementioned compounds of formulas I, II, and III; ethynyl p-tolyl sulfone; ethynylbenzene sulfone; ethynyl 4-methoxybenzene sulfone; ethynyl 4-n-hexoxybenzene sulfone; ethynyl 4-nitrobenzene sulfone; ethynyl 4-chlorobenzene sulfone; ethynyl 4-bromobenzene sulfone; ethynyl 2-methylbenzene sulfone; ethynyl 3-methylbenzene sulfone; and ethynyl 2,4,6-trimethylbenzene sulfone. Preferred alkynyl sulfones incorporated in the biocidal concentrate include, but are not limited to, ethynyl 4-methylbenzene sulfone, ethynyl 4-methoxybenzene sulfone, iodoethynyl 4methylbenzene sulfone, iodoethynyl 4-methoxybenzene sulfone, and combinations thereof. Biocides are materials that prevent the growth of, inhibit the growth of, or kill microorganisms, including, but not limited to, bacteria and fungi. Interestingly, the halogenated haloalkynyl aryl sulfones of the present invention remain biocidally effective even after cursory decomposition, i.e., loss of the halogen.
Generally, the biocidal concentrate further comprises from about 1 to about 10%, preferably from about 1 to about 5%, by weight of a solid or liquid formulation adjuvant and up to 15%, preferably from about 0.5 to 10%, by weight of one or more surfactants, based upon 100% weight of total biocidal concentrate.
The compositions may also comprise further auxiliaries, such as wetting agents, adhesives, emulsifiers, preservatives, fillers, carriers, viscosity and pH regulators, binders, tackifiers, fertilizers, other active ingredients, and any combination of any of the foregoing. Other conventional adjuvants may be added to the composition for different applications as known to those of ordinary skill in the art.
The alkynyl aryl sulfones may be incorporated into different formulations including, but not lim

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