Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1994-10-21
1995-11-07
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
A01N 3302
Patent
active
054648734
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/a13 93/01125, filed May 28, 1993.
FIELD OF THE INVENTION
This invention is in the field of the control of fungal infection in plants.
DESCRIPTION OF THE PRIOR ART
The effect of compounds which interfere with polyamine metabolism on the growth of the fungus Botrytis cinerea has been investigated, Smith et al., J. Gen. Microbiol. 136, 985 (1990). This work demonstrated that difluoromethylornithine, (DFMO) inhibition of fungal growth could be reversed with the addition of putrescine, cadaverine, spermidine and spermine. "Butenediamine" itself caused some inhibition of fungal growth but significantly reversed the inhibitory effect of DFMO.
SUMMARY OF THE INVENTION
We have now discovered that certain alicyclic diamines exhibit useful antifungal activity.
Accordingly, the invention provides the use of a compound having the general formula (1): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 which may be the same or different represent hydrogen atoms or alkyl groups of 1-6 carbon atoms or NR.sup.1 R.sup.2 and/or NR.sup.3 R.sup.4 together represent a heterocyclic group having 5 or 6 ring atoms, x is 0 or 1 and when x is 0 the dashed line represents a double bond, W represents a saturated or ethylenically unsaturated divalent hydrocarbyl group required to complete a cycloalkane, cycloalkene or cycloalkadiene ring of 3 to 6 ring atoms, preferably 4 to 6 ring atoms, and from 0 to 2 double bonds, in the form of a free base or acid addition salt tolerable to plants, as a plant fungicide.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
One class of preferred compounds of formula (1) is those wherein W completes a cycloalkane or cycloalkene ring of 4 to 6 ring atoms. W represents preferably a group having the formula--(CH.sub.2).sub.n -- wherein n is from 2 to 4 or a group --CH.sub.2 --CHyR.sup.5 ---CHyR.sup.6 --CH.sub.2 -- wherein y is 0 or 1 and when y is 0 the dashed line represents a double bond and R.sup.5 and R.sup.6 which may be the same or different represent hydrogen atoms or alkyl groups of 1 to 4 carbon atoms, especially methyl groups.
R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are preferably alkyl groups of 1 to 4 carbon atoms, especially methyl, or hydrogen atoms.
One particularly preferred class of compounds for use as a plant fungicide is tran s-N,N,N',N'-tetramethyl or -tetraethyl-1,2-bis(aminomethyl)cyclobutane [better named trans-1,2-bis(dimethylaminomethyl or diethylaminomethyl)cyclobutane] and also 1,2-bis-(methylaminomethyl or ethylaminomethyl)cyclohexa-1,4-diene.
Others are the primary amines, (R.sup.1,R.sup.2,R.sup.3 and R.sup.4 are all hydrogen). Within this group, particularly preferred compounds are 1,2-bis(aminomethyl)-4,5-dimethylcyclohexa-1,4-diene and 1,2-dimethyl-4,5-bis(aminomethyl)cyclohex-1-ene, of which the trans isomer is more preferred than the cis isomer.
Preferred heterocyclic groups NR.sup.1 R.sup.2 and/or NR.sup.3 R.sup.4 are pyrrolidino, piperidino, 4-methylpiperidino and morpholino.
All these diamines can form salts with mineral acids or organic acids. Preferred mineral acids are HCl, HBr, HNO.sub.3, H.sub.2 SO.sub.4, H.sub.3 PO.sub.4. Preferred organic acids are propionic, benzoic, formic, acetic, trifluoroacetic, maleic, fumaric, succinic, malonic, tartaric, ascorbic, citric, oxalic, glyoxalic, alkyl or anyl sulphonic. These salts may be prepared by standard techniques and procedures well known in the art.
The compounds of the invention may be prepared by conventional techniques in organic chemistry and/or techniques analogous to those of the Examples herein, e.g. substituting pyrrolidine or morpholine for aliphatic amines.
The diamine compounds of the Invention also exhibit antifungal activity when prepared in the form of their acid salts and such salts may be used as fungicides according to this invention. The compounds of the invention are particularly useful fungicides against fungi of the genera Erysiphe and Podosphaera. These fungi cause mildew in plants. Thus the compounds of the invention are particularly useful mildewicides.
This
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Robins David J.
Walters Dale R.
British Technology Group Limited
Robinson Allen J.
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