Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1993-11-19
1997-02-04
Kumar, Shailendra
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
514631, A01N 3304
Patent
active
055998470
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB92/00964 filed May 28, 1992.
1. Field of the Invention
This invention is in the field of the control of fungal infection in plants.
2. Description of the Prior Art
Polyamines are essential for the growth and development of all organisms, including plants and fungi. However, whereas plants possess two pathways for polyamine biosynthesis, i.e. via the enzymes ornithine decarboxylase [ODC] and arginine decarboxylase [ADC], fungal polyamine biosynthesis appears to be a result of ODC activity only.
Plants are attacked by a wide range of fungi which are the cause of considerable losses of yield and quality. Since fungi possess only the ODC pathway of polyamine biosynthesis, the inhibition of this enzyme should control their growth.
Such inhibitors have been extensively researched but the major breakthrough was directly attributable to the synthesis of enzyme-activated irreversible inhibitors of ODC and ADC notably difluoromethylornithine [DFMO], which has been tested as an anti-cancer agent and also as an anti-parasitic agent, and difluoromethylarginine [DFMA].
Recent work has shown that DFMO can reduce fungal growth and has led to the investigation of the use of DFMO as a fungicide, see for example N088/02986 (Weinstein and Galston) and U.S. Pat. No. 4,760,091 (Carson et al.).
The effect of compounds (including DFMO) which interfere with polyamine metabolism on the growth of the fungus Botrytis cinerea has been investigated (Smith et al., J. Gen. Microbiol. 1990, 136, 985). This work demonstrated that the DFMO inhibition of fungal growth could be reversed with the addition of putrescine, cadaverine, spermidine and spermine. "Butenediamine", caused some inhibition of fungal growth but significantly reversed the inhibitory effect of DFMO.
SUMMARY OF THE INVENTION
It has surprisingly been found that certain derivatives of 2-butene-1,4-diamine exhibit considerable anti-fungal activity. Accordingly, the invention provides the use as a fungicide of compounds having the general formula (I) below: different represent a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a cycloalkyl group having from 3 to 6 carbon atoms, a heterocyclic group, an aryl group, a heteroaryl group, having from 3 to 6 atoms or an amidino group or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together represent a carbocyclic or heterocyclic group comprising from 3 to 6 atoms, with the proviso that R.sub.1, R.sub.2, R.sub.3 and R.sub.4 cannot simultaneously represent hydrogen atoms.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The antifungal activity of the compounds of formula (I) is thought to be due mainly to their properties of polyamine metabolism interference. However, other mechanisms may play a role in the activity of these compounds as antifungal agents.
The groups R.sub.1, R.sub.2, R.sub.3 and R.sub.4 in formula (I) may be the same or different. Preferably the groups R.sub.1 and R.sub.2 identical and the groups R.sub.3 and R.sub.4 are identical and even more preferably, the groups R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are all identical.
Preferred compounds are those wherein at least one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are alkyl groups, preferably having 1 to 3 carbon atoms. More preferably at least one of R.sub.1 and R.sub.2 and at least one of R.sub.3 and R.sub.4 represents an alkyl group having from 1 to 3 carbon atoms.
A particularly preferred compound is E-(N',N'-dimethyl)-1,4diaminobut-2-ene.
Another preferred group of compounds are those wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 all represent alkyl groups having from 1 to 4 carbon atoms. A particularly preferred compound is E-(N,N,N',N-tetraethyl)-1,4-diaminobut-2-ene (TED).
The compounds of formula (I) may be synthesised using the conventional techniques of synthetic organic chemistry. The substituted diamines may be synthesised by displacement of bromine from (E)-1,4-dibromo-2-butene by a primary or secondary amine.
The compounds of formula (I) also exhibit antifungal activity when prepared in the form of their aci
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patent: 2415020 (1947-01-01), Morey
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patent: 4760091 (1988-07-01), Carson et al.
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patent: 5283367 (1994-02-01), Babiarz et al.
Smith et al., J. of General Microbiology, 1990, 136, 985-992.
Patent Abstracts of Japan, vol. 14 No. 539. 28 Nov. 1990.
Chemical Abstracts, vol. 84 No. 1, 5 Jan. 1976. Abstract # 1710c. Noel et al "Potent inhibition of . . . ".
Robins David J.
Walters Dale R.
British Technology Group Limited
Kumar Shailendra
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