Oxaboroles and salts thereof, and their use as biocides

Details Oxaboroles and salts thereof, and their use as biocides Oxaboroles and salts thereof, and their use as biocides

1996-12-09

1999-03-09

Morgan, Kriellion S.

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

524111, 424405, 514 64, 558288, 558290, 558291, C08K 515, A01N 5508, C07F 504

Patent

active

058801880

DESCRIPTION:

BRIEF SUMMARY
This application is the national phase of international application PCT/GB95/01206 filed May 26, 1995 which designated the U.S.
The present invention relates to the use of oxaboroles and salts thereof as industrial biocides, especially fungicides, biocidal compositions containing the oxaboroles including their salts and certain oxaboroles.
No single industrial biocide is ideal for all applications and new biocides are constantly being sought with better activity against individual spoilage micro-organisms, wider spectrum of activity, improved compatibility with the medium in which they are used and improved persistence in use. Safety in use is another important consideration.
A small number of compounds containing an oxaborole ring (hereinafter "oxaborole") have already been described in the literature. These are N-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-yl)-succinamic acid (CA 55 23423c); 4-(1,3-dihydro-1-hydroxy-2,1-benzoxaborol-6-ylazo)-2-naphthoic acid (CA 55 23423c); 1,3-dihydro-1-hydroxy-6-nitro-2,1-benzoxaborole (CA 55 23423b); 6-amino-1,3-dihydro-1-hydroxy-2,1-benzoxaborole and its hydrochloride (CA 55 23423c); 1,3-dihydro-1-hydroxy-7-methyl-2,1-benzoxaborole (CA 55 6473f); 1-(benzyloxy)-1,3-dihydro-2,1-benzoxaborole (CA 61 16084f); 1,3-dihydro-1-hydroxy-N,N-dimethyl-2,1-benzoxaborol-6-amine (CA 1(3) 22633f); 4-bromo-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (CA 1(3) 22633f); 1-(cyclohexyloxy)-1,3-dihydro-2,1-benzoxaborole (CA 61 16084f); 1-ethoxy-1,3-dihydro-2,1-benzoxaborole (CA 61 16084f); 61 14698a); 1,3-dihydro-1-hydroxy-6-methyl-2,1-benzoxaborole (CA 61 14698b); 5-bromo-1,3-dihydro-1-hydroxy-2,1-benzoxaborole-6-methanol (CA 51 boronophthalide (CA 116(13) 129587q). French certificate of utility No 73 29370 discloses boronophthalide (1-hydroxy-3H-1,2-benzoxaborole) and this is the only citation known which discloses that an oxaborole is biologically active. It is disclosed as being useful in inhibiting the growth of micro organisms in aviation fuels. However, at least 100 ppm of the boronophthalide is required to protect the fuel.
It has now been found that compounds containing an oxaborole ring are particularly effective against micro-organisms such as bacteria, algae, yeasts and particularly fungi, especially fungi which cause degradation of plastics materials. The level of microbiological activity now found is surprising in the light of the disclosure in the above utility certificate.
According to the present invention there is provided a method for the protection of a medium susceptible to microbial attack by the treatment of the medium with an effective amount of an oxaborole of general formula (1) ##STR1## or a salt thereof wherein
A and D are each independently, hydrogen, optionally substituted C.sub.1-8 -alkyl, aralkyl, aryl, or heterocyclyl or where A and D together with the carbon atoms to which they are attached form a 5,6 or 7-membered fused ring which itself may be substituted;
X is a group --CR.sup.1 R.sup.2 wherein R.sup.1 and R.sup.2 are each, independently, hydrogen, optionally substituted C.sub.1-6 -alkyl, nitrile, nitro, aryl or aralkyl or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form an alicyclic ring;
R is hydrogen, optionally substituted C.sub.1-8 -alkyl, aralkyl, aryl, heteroaryl, cycloalkyl or a radical of formula (2) ##STR2## wherein A, D and X are as hereinbefore defined except where the medium is aviation fuel and the only oxaborole is boronophthalide.
When A and/or D is alkyl, it may be linear or branched and is preferably C.sub.1-12 -, more preferably C.sub.1-8 - and especially C.sub.1-4 -alkyl.
When A and/or D is substituted alkyl, the substituent may be C.sub.1-6 -alkoxy, hydroxy, halogen, nitrile, amino, substituted amino, carboxy, acyl, aryloxy or carbonylamnino optionally substituted by C.sub.1-6 -alkyl.
When A and/or D is alkyl the alkyl group or groups are preferably unsubstituted.
When A and/or D is aryl, it is preferably phenyl which may itself be substituted.
When A and/or D is aralkyl, it is preferably benzyl or 2-ethyl

REFERENCES:
patent: 3104255 (1963-09-01), Emrick et al.
patent: 3361672 (1968-01-01), Andress, Jr. et al.
patent: 3655775 (1972-04-01), Nauta
patent: 3686398 (1972-08-01), Kohn et al.
Dale et al: "Substituted Styrenes VII The Synthesis and Some Reactions of the Vinylbenzeneboronic Acids", The Journal of Organic Chemistry, vol. 27, 1962, pp. 2598-2603, Table 1, compounds 19 and 20.
Cummings et al: "Arylboronic Acids. A Medium-size Ring Containing Boronic Ester Groups", The Journal of Organic Chemistry, vol. 34, 1969, pp. 1669-1674. see the whole document.
Tschampel et al: "Arylboronic Acids VII. Some Reactions of O-Formylbanzeneboronic Acid", The Journal of Organic Chemistry, vol. 29, 1964, pp. 2168-2172. see the whole document.
Grassberger:"Zum Abbau Von 1,2-Dihydro-1-Hydroxy-2-Organosulfonyl-2,3,1-Benzodiazaborinen Und-Thieno83,2-D)(1,2,3)Diazaborinen in Alkalischer Wassriger Losung", Liebigs Annalen Der Chemie, 1985, pp. 683-688, cited in the application * Compound 5 *.

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