CA2230102A1

CA2230102A1 - Agents with antifungal activity and methods of use thereof

Info

Publication number: CA2230102A1
Application number: CA 2230102
Authority: CA
Inventors: Latchezar S. Trifonov; Priyotosh Chakravarty; William A. Ayer; Yasuvuki Hiratsuka
Original assignee: University Of Alberta; Latchezar S. Trifonov; Priyotosh Chakravarty; William A. Ayer; Yasuvuki Hiratsuka
Current assignee: University of Alberta
Priority date: 1996-06-21
Filing date: 1997-06-20
Publication date: 1997-12-24
Also published as: AU3103697A; WO1997048279A1

Abstract

An antifungal composition is disclosed comprising at least one compound selected from the group consisting of: (a) at least one compound of formula (I), and (b) at least one compound of formula (II), or an alkali or alkali earth salt thereof, and a carrier or diluent therefor. Methods of reducing or inhibiting fungal growth, fungal wood decay and fungal wood stain are also disclosed, along with a method of reducing or inhibiting fairy rings. Paints, stains, cleaning products, disinfectants and wood or lawn treatments containing the compounds are also disclosed.

Description

W O 97/48279 PCT~B97/007S0 AGENTS WlTtJ ANTIFUNGAL ACTIVITY AND METHODS OF IJSF
THEREOF

This application claims priority from provisionai application Serial No. 60/020,035, filed June 21, 1996.

5 Background Of the Inventiion This invention relates to compounds that have antifun~al activity.
These compounds reduce or inhibit the growth of fungi from a variety of genera and species.

Trembling aspen or aspen (Populus tremuloides Michx.) is an 10 important source of pulp for the paper-making industry. Aspen is also used for making particle board and solid wood products. Decay and stain caused by several fungi have been identified as the two most important factors limiting the use of aspen (Hiratsuka et al. 199û, 1995~. Recently, the present inventors reported on the inhibition of the growth of aspen 15 decay and stain fungi using certain antagonistic fungi (Chakravarty and Hiratsuka 1992, 1994; Chakravarty et al. 1994; Hutchison et al. 1994). The growth of aspen decay fungus Phellinus tremulae ~Bond.) Bond. et Borisov was inhibited by metabolites of another decay fungus Peniophora polygonia (Pers.:Fr.) Bou. et Gal. (Trifonov et al. 1992). The antagonistic 20 activity of the coprophilous fungus Sporormiella simiJis Khan and Cain, frequently found on aspen black gali, as well as the activity of its metabolites were also studied (Chakravarty et al. 1994). It was shown that S. similis inhibits the in vltro growth as well as aspen wood chip colonization by blue stain fungi. The present invention is an extension of 25 work reported on the antifungal activity of metabolites of Peniophora poJygonia (Trifonov et al. 1992) and SporormielJa similis (Chakravarty et al. 1994) against aspen pathogens.

CtlNrlnl\1~10N COPY

W O 97/48279 PCT~B97/00750 Summary of the Invention The inventors extracted a variety of compounds ~rom decay fungus Peniophora polygonia and found that isobutyric and isovaleric acid were amongst the most active compounds. Following this lead, they tested 4-S phenyl-3-butenoic acid - a structural analog of the above acids. 4-phenyl-3-butenoic acid is known as a potent mechanism-based inhibitor of peptidylglycine amidating monooxygenase (Bradbury et al. 1990; Rhodes and Honsinger 1993), as a modulator of the activlty of y-glutamic acid transpeptidase (Thompson and Meister 1980), as well as an antibacterial 10 compound (Khristov 1973).

The objective of this invention is to provide an antifungal composition and methods of use against a wide range of fungi. Specifically, the invention is directed to methods of re~ cing or inhibiting fungal growth by applying the conll)o~ulds of the invention to a region to be treated. The antifungal compositions of the 15 invention can be used against a wide variety of fi ngi, and it is well within the skill of an ohlhl~ worker in the art to screen particular fungi against which the compositions of the invention are effective.

The objective of part of this invention was to determine the activity of homologs and analogs of 4-phenyl-3-butenoic acid against P. tremulae and two 20 species of blue stain fungi, Ophiostoma piliferum (Fr.) H. and P. Sydow and O.
crassivaginatum (~.D. Griffin) T.C. ~rnngtcln For cc ,npa~iso~ purposes, phomalone (Ayer and Jimenez 1994), pentachlorophenol, copper 8-oxyquinolinate, Zn salt of 1o-lln~lpcenoic acid, as well as lauric acid were included in this study.

The inventors have also found that tiglic acid and senecioic acids, minor 2~ metabolites of S. similis, significantly inhibited the growth of the blue stain fimgus Ophiostoma piliferum, even at concentrations as low as 1 ~lg/ml. The inventors therefore synthPsi7P~ derivatives and analogs of these two leads to test their activity against the aspen decay fungus Phellinus tremulae and the aspen blue stain , WO 97/48Z79 PCT~B971007~0 fi~ngi Ophios~oma crassivaginatum and 0. piliferum.

Selected com~ ds from the derivatives, homologs and analogs of tiglic acid, senecioic acid and 4-phenyl-3-butenoic acid were also tested against the conifer decay fimgi Phellinus pini and ~aematostereum sanguinolentum and the - 5 conifer blue stain fimgi Ophiostoma clavigerum and 0. ips. Finally, select compounds were tested against the fairy ring f~ngus Marasmius oreades.

Thus, ~e l~lc;s~llLly-disclosed compounds include deliv~ s, homologs and analogs of tiglic acid, senecioic acid and 4-phenyl-3-butenoic acid which are ~;Live ~ntifim~l compounds. These compounds can be used in ~lli compositions, and methods of reduc;ng or inhibiting fungal growth.

More specifically, the present invention is directed to an antifungal co,~ o~i~on compri~in~ at least one compound selec~ed from the group con.~i~t;n~of:

(a) at least one compound of formula I

R- ~3 R C C (CH2)n COOR6 _ h 1 5 wherein R~ is selecte~ from the group con~i~ting of (1) H, (2) Cl-C~5 alkyl, (3) a group R~

R~

W O 97/48279 PCT~B97/00750 wherein R7 and R8 are Cl-CIs alkyl or, together with the carbon ...
atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wht;~ Ar is an aromatic ring;
R2 through Rs are each independently H or C~-C~5 alkyl, or R2 and R3 5 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or RZ and R3 together, and R4 and Rs together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R' through R5, together with the carbon atoms to which they are bound, fo~n part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through Rs are each H, then Rl is only Ar;
R6 is selected from the group consisting of (l) H, (2) Cl-C~5 alkyl, (3) phenyl, (4) a group N(CH3)2(CloH2,)2, (5) a group N(CI-Cl5 alkyl~4, wherein the alkyl groups are the same or different, (6) NHm~X)4 ,l" wherein each X is~5 independently selected from Cl-CI5 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when Rl is Ar, then R6 is other than phenyl;
nisO-lOandn'isOor l;and (b) at least one compound of formula II

R9~ R~' R
.

W O 97/48279 PCTnB97100750 Wil~
R9 is seiected from the group con.~i~ting of H, OH and C,-C,5 alkyl;
R'~ is H or OH; and Rl' and Rl2 are each indepen~7P-ntly H or C,-CIs alkyl, or an alkali or alkali earth salt thereof, and a carrier or diluent therefor.

It is ~l~r~lc;d that Ar is s~lecte~ from the group consict;ng of 10 wherein each of the rings may have non~ fe,hlg substihlpnt~ thereon.

The present invention also re~ates to a method of re~ cing or inhibiting fungal growth in a region to be treated, comrri~;ng applying to the region a fungal rerl~lr-ing- or inhibiting-e~cli~ amount of at least one compound selected f~om the group con~ictin~ of:

(a) at least one conlpoLIlld of fiorml7~,7 I, wherein formula I is as defined above; and (b) at least one compound of formula II, wherein formula II is as defined above, or an alkali or alkali earth salt thereof.

W 097/48279 PCT~B97/00750 .

The more ~fer~lled embonim~nt~ of the present invention are disclosed in the Detailed Description of the Invention, as follows.

Dt,~ tion of the ~r~f~. I ed Embodiments In a ~irst aspect, ~e present invention is di~ ,L~d to an ~ntifimg~l 5 co~ o~ilion co,1~ g at least one compound selected from the group Con~i~ting of:

(a) at least one compound of fonm ~- R3 Rl C C (CH,)~, .COOR6 R4 R~ ~

wl~
R' is select~d from the group COn~ lg of (1) H, (2) C,-C,5 ~ 1, (3) a 1 0 group R\

wherein R7 and Rg are Cl-C,5a~ or, together with the carbon W O 97/48279 PCT~B97100750atoms to which tbey are bound, f~rm a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C,-C15 alkyl, or R2 and R3 are a bond thus creating a double bond between the carbon atoms to which they are 5 bound, or R2 and R3 and R4 and R5 are bonds thus creating a triple bond bc;l~
the carbon atoms to which they are bound, or two of R~ thrt~ugh R5, together with the carbon atorns to which they are bound, folm part of a 3-8 ~.~I)eled carbocyclic ring, with the proviso that when R2 through ~5 are each H, t~en R~ is only 10 Ar;
R6 is s~l~cte~ om the group cn...~ o~(1) H, (2) C,-C15 alkyl, (3) phenyl, (4) a group N~C~I3)2(C",H2,)2, (5) a group N(C,-CI5 allcyl)4, wherein the alkyl groups are the sarne or ~Iirr~G~lt, (6) NHm(X)~,I" wherein each X is independently selected from Cl-C~s alkyl arld 2-hydroxyethyl, and m is 0-4, 1~ with the proviso that when R' is Ar, then R6 is other than pheny~;
n is O-lO and n' is O or l; and (b) at least one compound of for~nula II

R9 ~ < Rl' wherein - R~ is selected i~om the group consisting of ~, OH and C,-C~s allcyl;
R'~ is H or OH; and W 097/48279 PCT~B97/007S0 Rl l and Rl2 are each independently H or (~,-C,5allcyl, or an alkali or alkali earth salt thereof, and a carrier or diluent therefor.

Unless otherwise spe~ifie~l ~r is preferably selected from the group ~o~ Lil~g of wherein each of the rings may have non-interfering substit~lPntc thereon. Non-Ç~"illg substituents can include, for exarnple, but are not limited to, lower all~yl 10 groups, lower alkoxy groups, lower acyl groups, am;no groups, hydroxyl groups, etc. The terrn "lower" is u~derstood as meaning 1-6 brarlched or unbranched carbon atoms. Usually, monocyclic rings may have 0-2 substitnpntc~ and bicyclic rings may have 0-4 substi~l~nt~ but this number is not critical.

There are generally four classes of p.~ .d compounds. A first class is 1~ cc,.l.~ou.lds of forrnula III

Rl ~ C~O~ 6 wherein R~3 through R'5 are each independently H or C~-C ~5 alkyl, or two of R'3 W O 97/48279 PCT~B97/00750 through R'5, toget~er with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and R~ is as defined above.

A second class of ~Ic~l~ed compounds are co.u~ou.lds of forrn R~
Q~

~; W~ 1G~1 R6 through R8 and n are as defined above.

A third class of ~lG~lled compounds are compounds of forrnula V

RJ~ ~18 2)n--COO~LI
R'~ R~

wherein Rl6 is a group Ar, WLC1~ Ar is as defined above;
R'7 through R20 are each H, or R'' and Rl8 are a bond thus creating a double bond between the carbon atoms to which they are bourld, or Rl' and Rl8 and Rl9 - and R2~ are bonds thus creating a triple bond between the carbon atoms to which they are bound;

W 097/48279 PCT~B97/00750 R2' is selected ~om the group con~i~tin~ of (1) EI, (2) C,-C,5 alkyl, (3) a group N(CH3)~(C~oH7~)2~ (4~ a group N(C,-C,s alkyl)4, wherein the alkyl groups are the same or difr~rc.ll, (5) NH",(X)~m, wherein each X is independently selected from C,-CI5 alkyl and 2-hy~l.v~y~lyl, and m is û-4; and n is as defined above. '' The fourth class of ~lef~ ,1 compounds are cor~oul~ds of fonn~

R

R9 ~) Ç~ Rl' R~

wherein R9 through Rl2 are as defLlled above.

In another aspect, the present invention is directed to a method of reducing or inhibiting fungal growth in a region to be treated, comrri~ing applying to the 10 region a fungal re~ ring- or inhibiting-effeetive amount of at least one compound selected from the group consi~ting of:

(a) at least one compound of forrnula I, wherein forrnula I is as defiIled above, and (b) at least one colllpou,ld of formula II, wherein formula II is as defined 1 ~ above, or an alkali or alkali earth salt thereof.

W 097148279 PCT~B97/00750 The term "antifimgal" as used herein includes, but is not limited to, compounds that reduce, destroy or '.cill fungi (fungicidal) or innibit the growth of fungi (filngi~t~tic). The terrn "antifimgal composition" as used herein includes not only the compounds of the present invention in a conventional diluent and/or solvent, but also inrlll~es the compounds of the present invention in other carriers and/or fi~al ~le~ ;on~, such as paints, stains, wood stains, elt ~n~rs, tli~ii"re~ , rinses and wood or lawn Lr~i~lr~

The term "wood" as used herein inrhl~ec, but is not lir~uted to, trees, logs, woody plants, wood products, wood chips, processed wood, saw dust or items 10 made completely or partially of wood.

The term "wood tre~trnent" includes, but is not limited to, washes. rinses, stains, pigrnented fini~hec, natural fini~he~, exterior fini~h~, interior fini~htos, ru~ c fini~he~, filling, washcoating, sealing, topco~ing, cleaners, polishes or fire ~eL~L~d~lL~. Preferred tre~trnent includes oil based or water based l~ni~h~s The term "region" refers not only to the surface of the area to be treated, but also to areas lmcl~rn.~th the surface, if the surface is permeable. For example, the term "region" applies not only to the surface of soil having plants thereon, but also to areas lm~rne~th the soil surface. Similarly, the term "region" includes the inner portion of wood below the surface of the wood. However, the term "region" is also meant to include the surface of non-permeable substrates, such as bathroom tile or kitchen coLl~ Lops, or non-permeable painted s-lrf~s.

Herein, the term "alkyl" is a radical co..li.;..i..~ only carbon and hydrogen, and lacking double or triple bonds. In this invention, unless stated otherwise, alkyl radicals contain 1 to 15 carbons and, unless stated otherwise, the alkyl radicals can 25 be branched or unbranched.

The antifungal compositions of the present invention are effective against a W O 97148279 PCT~B97/00750variety of genera ~nd species of fungi. Preferred fungi against which the present compositions are effective include the genera Phellinus, Ophiostoma fCeratocystis), Haematostereum and ll~arasmius. Preferred species include P.
tremulae, P. pini, O. crassivaginatum, O. piliferum, O. clavigerum, O. ips, H.
5 sanguinolentum and M. oreades.

Preferred woods to be treated include aspen and conifers.

This invention also in-~.h~ c the use of the present compounds in a method for the tre~tm~llt of wood or wood products to reduce or inhibit decay a~d/or st~ining comrri.~in~ applying to a region to be treated a fungal-decay andlor 1 () fungal-st~inin~ re~ ring- or inhibiting-erf~ilivt: amount of at least one coll~o~ld selected from the group co~ lhlg of:

(a) at least one compound of formula I, wherein formula I is as defined above; and (b) at least one compound of formula II, wherein forrnula II is as defined 1 5 above, or an alkali or alkali earth salt thereof.
.

This invention also incll~les the use of these compounds in a method of treating fairy rings comprising applying to a region to be treated a fairy-ring fungal reducin~- or inhibiting-effective amount of at least one compound selected from the group con~i~tin~ of:

(a) at least one compound of formula I, wherein formula I is as defined above; and (b) at least one compound of formula II, wherein formula II is as defined above, or an alkali or alkali earth salt thereof.

It is l3lcr~ d to use these compounds to reduce or inhibit t~e grow~h of fairy rings on grassy regions (e.g., golf courses and other grassy lawns).

The compounds of the present invention can be used in pa~nts, stains, wood stains, cleaners, disil~cL~lL~, rinses or other wood k~ .CntC The compounds can 5 aiso be u~sed for other plants besides woody plants and ~accec Although ~
for wood, grasses and other plants are preferred, ~e compounds of the present invention can also be ~ced on non-wood ~-- r~C~s as an active agent of çl~nf~rs,di~ fe~ or rinses, such as ~athroom or kitchen c3e~nt?r~, cleaners for non-wood ~e.g., ~ ll;lllllll or vinyl) house siding or other ~ ning products or 1 0 disinfectants where reducing or inhibiting fungal grow~ is desired.

With reference to the numerical listings of vanous co~ ou~ds of the invention in Tables 1-7, the following compounds are ~re~.-ed ~or the following uses:

~ The use of one or more of the following compounds in a me~od for 1 5 reduction or inhibition of fungal growth: la, le, lf, 2, 4a, 4b, 6a, 6d, 7, 8a, 8c, 8f, 9a, 9b, 13, 14, 15,20, 21a, 21d, 21e,22, 24,25d, 31, 32, 33, 34, 26a, 26b, 26c, 26d, 26e, 26f, 26g, 28, 29, 23a and 35. The use of at least one of the followingcompounds is especially preferred: la,2, 4b, 7, 8f, 13, 14, 20,21a, 26c, 26d, 26f, 28, 31 and 32.

~ The use of one or more of the folIowing compounds in a method for reducing decay and/or staining of wood: la, 2, 4b, 7, 8c, 8f, 13, 14, 3:~, 34, 20, 21a, 21e, 24, 26b, 26c, 26d, 26f, 28, 31 and 32.

~ A method for reducing wood staining using one or more of the following compounds: la, 2, 4a, 4b, 6a, 7, 8a,8c, 8f, 9a, 9b, 13, 14, 20, 21a, 21d, 21e, 22, 24, 26b, 26c, 26d, 26f, 28, 31 and 32 .

, W O 97t48279 PCTAB97/00750 ~ A method for re~ ing wood decay using one or more of the followin~
compounds: 1~, le, 2, ~b, 7, 8c, 8f, 13, 14, 15, 33,34, 20, 21a, 21e, 24, Z~d, 26c, 26d~ 26f, 26g, 28, 31 and 32.

., ~ A method for reducing or inhibiting growth of fairy ring fungus growth using one or more of the following compounds: la, 8f, 13, 14, 21a, 26d, 32 and 35.

An ~ntifi-ngsll composition in accol~ce with the present invention ef~,.ably contains at least one of the following compounds: la, le, lf, 2, 4a, 4b, 6a, 6d, 7, 8a, 8c, 8f, 9a, 9b, 12, 13, 14, 15, 33, 34, 20, 21a, 21d, 21e, 22, 23a, 24, 25d, 26a, 26b, 26c, 26d, 26e, 26f, 26g,28, 29, 31, 32 and 35. More ~ d are 1 0 at least one of the following compounds: la, le, lf,2, 4a, 4b, 7, 8c, 8f, 12, 13, 14, 20, 21a, 26b, 26c, 26d, 26f,28,31,32, 33, and 34, and most preferred are at least one of the following compounds: la, 2, 4b, 7, 8c and 8f.

An antifungal composition and method of use for re~ ing or inhibiting fungal growth preferably inc~ two or more compounds to increase the bread~h 1 5 of OL~ inhibited or reduced, or to increase the potency of the compounds. It is particularly preferred to use at least one compound of the present invention,along with benzoic acid and/or salicylic acid. Preferred compositions in this regard are compositions cont~inin~ benzoic acid and at least one of the following compounds of the invention: 8f, la, 13 and 14. It is ~l~r~l,ed to apply the 20 co.l,~o~lds in 50:50 ratios (ben~oic acid:compound(s) of the invention). However, a range of 25:75 to 75:25 is suitable.

Formulations The present compounds are soluble in at least one of acetone, alcohol and water. These compounds can also be dissolved in a variety of other solutions or 25 solvents. The compounds can also be directly added to a final ~ ~dlion (e.g.,paint, stain, wood or lawn treatrnent, cleaner or disinfectant). Tf the antifungal .

W O 97/48279 PCT~B97/007S0 compound will not readily dissolve in the final ~)lcy<~ ;OIt~ then the c~n{ o~ d must be first dissolved in an ~u~-iate organic solvent and then diluted, as known in the art. The ~y~v~l;ate solvent must dissolve the compound and be able to rnix with the final p,.,~dlion. A worker skilled in the art can readily ~let~rrnine the 5 ~ .~liatesolventwithoutundue~ nt~tion. Thedesiredamountofthe ~ntifimF~;~1 compounds in the composition is between l and 50 times the amount which inhibited 95 to 100% of fungal growth ~accordill~ to ;.- rO. . . ~;~I;on from Tabies l to7,fore~mple). Thecu..~ ionofthe ~..1;r,."~,.l co~l~oulldsinthe composition is not critical. Normally, however, the ch~ ion range will be from 0.1% to 50%, more ~r~r~ d 1% to 30%. It is well within the Ol lhl~ y skill of a worker in the art to (let~-rrnin~ suitable amounts and con~ ~ntr~ti~ ns of the specific ~ 1 composition to be form~ tt?ll, dc~illg on the treatmPnt strategy.

One or more of the present compounds can be applied to wood using a 15 variety of methods in~ in~ but not limited to using a brush Ll~ t, dipping, seeping, diffusion, spraying, dusting, ~c;s~ processes or ground line tre?~trnt~nt~

The basic forrnulations for wood tre~tments, cleaners and disil~ ~ are known to those skilled in the art.

Formulations for other applications may include but are not limited to 20 solutions, emulsions, suspensions, dusting powders, lyoI~hi1i7~d solutions, liposome form~ tions or slow release form~ tions. These forrn~ tions can include a variet,v of additives including solvents, lipids, b1~ffering chemicals, d~Le.~e~ , fertilizers or other nutrients. Pl~ d dLion of specific fnrrn~ tion~ is well within the skill of an ordinarv worker in the art, and will depend on the 25 particular L~edLme.lt strategy employed.

~,Y~ mrl~c -WO 97/48279 PCT~B97/00750The effect of, 8 homologs and analogs of 4-phenyl-3-butenoic acid against Phellinus tremulae. Ophiosroma crassivaginatum, and 0. piliferum was studied.
These compounds showed varied inhibition of the in viko growth and the wood chip colonization by these fungi (Table 1). Six of the compounds tested prevented the development of blue stain caused by 0. ~ ivaginatum and 0. piliferum in wood chips at conr~nlT~tions of lO llg/rnl (Table 3).

The effect of d~,i iv~lives and analogs of tiglic acid and senecioic acids, minor metabolites of S. similis, were also studied. Activity was tested against the aspen decay fungus Phellinus tremulae and ~e aspen blue stain fungi Ophiostoma crassivaginatum and 0. piliferum (Table 2).

The effect of selected compounds against the conifer decay fungi P~ellinus pini and Haematostereum sanguinolentum and the conifer blue stain fungi Ophiostoma clavigerum and O. ips were also studied (Tables 4 and j).

Table 6 shows the effect of selected con~ ds on the in vitro growth of fairy ring fungus l~arasmius oreades. Ta~le 7 shows the effect of ber~70ic acid alone and in combination with selected compounds on the in vitro growth of M.
oreades.

E~ample 1. Org~lniem~
Phellinus tremulae (P. tremulae, NOF 1464 = UAMH 7005), an aspen decay fungus and two species of blue stain fungi, O. crassivaginatum (NOF 1509 - Ceratocystiopsis crassivaginata), and 0. piliferum ~OF 1772) isolated from decayed and stained wood of P. tremuloides were used in this study. Two conifer decay fungi Phellinus pini (NOF 2231) and Haematostereum sanguinolentum (NOF 1 l 8) and two species of conifer blue stain fungi Ophiostoma cZavigerum (NOF 838) and 0. ips (NOF 684), isolated from conifers were also used in this study. These fungi were m~int~inecl at 5~C on 2% malt extract agar in McCartney ' W O 97/48279 PCTAB97/007~0 bottles until used and a~e deposited in the fimgal culture collechon at the Northern Forestry Centre, C.ln~ n Forest Service~ Edmonton, Alberta (NOF) under the listed accession numbers.

Marasmius oreades (~OF 2255) was obtained from a fairy ring and 5 ~ on malt extract agar.

le 2. ChPmi'!~
The mo~lifi~ti~n~ of the ~l.u~;LLue of the lead-compound la included:
Pst~ifir~tion (Ib), ~ub~iLulion of the phenyl group ~lc,d), replacement of the phenyl group by a naphthyl group (le,f ), introduction of a triple bond (2) and an 10 allenic group (3), reduction (4a,b), introduction of a cycloL).o~le ring (~), chain shul~el~ g (6, 7, 8), and chain elongation (9-12). Two dicarboxylic acids (10, 11) were also included in the study. The hydro~y~ ...ic acids 6b and 6c, phenyl~.o~ylloic acid (7), and hydro~inn~mic acid (8a) were considered as promising candidates because of their low toxicity and enzyme inhibitory activity 15 (Hodgins 1971, Kubata et al. 1974).

The methyl ester of 4-phenyl-3-butenoic acid was prepared by tre~ nt of the acid with diazomethane. The naphthyl analogs le and If (Table 1~ were synthe~i7e~1 from 1- or 2-naphthyl ~et~kl~hyde and malonic acid (Ment~er &
Pillon, 1950). l'he acetylenic acid 2 and the allene carboxylic acid 3 were 20 synthesi7~1 according to Shevchenko et al. 1974, Mansfield and Whiting, 1956,and Maer~l 1961. The saturated acids 4a, 8d, 8e, 11, and 12 were obtained by catalytic hydrogenation of the colle~ol,ding ullsdluLdL~d acids la, 6e, 6f, 9b, and 10 over Pd/C at 1 atm. The dicarboxylic acid 10 and the phenyl analog of sorbic - acid 9b were ~y~ ii7~(1 following the method of Stuart et al. (1886).

The identity of the synthetic compounds was based on three independent W O 97/48279 PCT~B97100750 criteria (usually m.p. proton NMR spect~n and IR spectrum).

Compounds la, 4b, 4c, 6a, 6b, 6c, 6d, 6e, 6f, 6g, 7, 8a, 8b, 8f, 9a, 13, 14, 16, 17, 18, 19, 33, 34, and 35 are commercially available and were purchased from Aldrich.

The modifications of the lead co~ ou,lds tiglic (20) and senecioic (21a) acids incl~ formation of metal and lt~ 01~;11l l l salts (21b-e), synthesis of esters (23b, 24) and amides (25), replArPm~t of the OH group with ~ul)~liLuled phenyl groups (senecioph-?none~ 26) removal of the methyl groups (acrylophenone 28 and its precursor 27, as well as the ~b~I; L~ r1 acrylophenones 29 and 30), and 1 0 repl~ ment of the methyl groups by a cyclohexane ring (31 32).

Compounds 20, 21a, and 22 are cornmercially available and were purchased from Aldrich. The Zn salt of senecioic acid was pl~cLL_d by stirring asuspension of ZnO in a dilute solution of senecioic acid. The amrnonium salt 21dwas plcpaL~ed by lL. cLL~ L of 21a with 1 equivalent of diethanolamine while for1 5 the ~ LLalion of the ammonium salt 21e the sodium salt of senecioic acid was treated with didecyldimethylamrnonium bromide. Tr~o~tn~nt of 23a (Nie~ki et al.
1887) with senecioic anhydride afforded the diester 23b (Keh~n~nn 1895). The ester 24 was obtained from phenol and 21a in the attempt to syntheci7~ 26b (Bragole et al. 1960). The amides 25a,b,c were obtained by treAtTn~nt of senecioyl chloride with the coL,e~oLlding amine, while 25d was prepared by acylation of A~ lAllilicacidwithsenecioicanhydride(~I.r...A~ 1909).Seneciophenone (26a), and its deL;vcLliv~s 26b, 26d, and 26e were ~yll~ ed by Friedel-Krafts reaction with b~n7t-n~, anisole (afforded a mixture of 26b and 26c) toluene, or isopropylbenzene (Smith 1949). Compounds 26c and 26f were prepared following the procedures of Dev (1956) and Sowrnithr m (1985~ respectively. Methylation of26f with di~omethane afforded compound 26g. Compounds 27 and 28 were prepared as described (Mzmr~ich et al. 1922). Con~n~tion of p- -WO 97/48Z79 PCT~B97/00750methylacetoph~none with ffirfural or cinnamic aldehyde afforded compounds 29 (Kostanecki 1896) and 30 (Scholtz, 1903).1-Cyclohexene-l-carboxylic acid (31) was obtained by ~Ik~lin~ hydrolysis of the cornmercial methyl ester. The unsaturated acid 32 was prepared by Wittig reaction of cyclohexanone (G. Fodor, 5 1961) followed by ~Ik~line hydrolysis ofthe ester.

The identity of all compounds was based on three criteria (usually m.p., 'H-nmr, and IR spectra).

The co~ r-;ial wood pL~ sel ~L~es 22 and 23a were also included in this study for colnp~ on purposes.

F~ rle 3. Improved ~y~h~ . of 4-phenyl-3-butynoic acid Metallic lithium (0.77g, 0.11 M) was added to a mixture of dry benzene (15 ml) and hexamethylphosphoric triamide (HMPT) (45 ml) under nitrogen at room tt;lll~ dlule and stirred until dissolved (approximately 2 h). A solution of phenylacetylene (10.2 g, 0.10M) in benzene (20 ml) was added dropwise and the 15 mixture was stirred overnight at room temperature. The reaction mixture was cooled to 0~C and a solution of ethylene oxide (5.72 g, 0.1 3 M) in dry bell~;elle ( I S
ml) was added dropwise. A~ter stirring for 24 hours at room temperature, the reaction mixture was q~nch~(l with ice and ~ a~ d with ether (3 x 150 ml). The ether extract was washed with water (3 x 150 ml), dried over sodium sulfate, 20 filtered and the solvent removed under vacuum. The residue was passed through a short silica gel column with petroleum ether:ether equals 1:1 to give pure 4-phenyl-3-butynol (7.2 g, 50%) as an oil. 'H n.m.r. (CDC13):7.45-7.38, (m,2H,aromatic), 7.33-7.25 (m, 3H, aromatic), 3.81 (t,J=6.5, 2H, H-C(l)), 2.80 (t, J=6.5, 2~, H-C(2)), 2.88 (br. s, lH, OH~.

A solution of CrO3 (2.67 g) in 8 ml of 30% H2SO4 was added dropwise to a W 097/48279 PCT~B97/00750 solution of 4- phenyl-3-butynol (lg, 0.0068 M) in acetone (35 ml) at 0~C. The reaction ~ ule was stirred for 30 minntes at 0~C and for 4 hours at room t~nl~ Lule. Saturated solution of NaCl was added and the organic m~teri~l was extracted with ether. The ether extract was dried over sodium sulfate, the solvent 5 removed and the residue recryst~lli7ç~1 from petroleum ether:benzene to give 4-phenyl-3-butynoic acid (0.3 g). The mother liquor was sub~ected to column chromatography with methylene chloride:ethanol equals 95:5 to provide ~ ition:~
amount of the acid (0.14g). Total yield 40~/O. M.p. 74.0-?5.5~C (Mansfield and Whiting, 1956; m.p. 71~C). I.r. ~CHC13): 3400-2600, 3051, 1690, 1428, 1087 cm~l.1 0 'H n.m.r. (CDCl3): 7.45 (dd, J=8.0, 2.0, 2~I, arom.), 7.38-7.30 (m, 3H, arom.), 3.62 (s,2H, H-C(2)).

Example 4. Bioass..y~
A. Agar cultures.
To test the effect of the above compounds on the in vitro growth of P.
15 tremulae, O. crassivaginatum, and O. piliferum, these fungi were grown on MULTIWELLTM Tissue culture plates (1.~. cm x 1.5 crh, rli~net~r x length, individual well; m~nllf~-~tured by Becton Dickinson Labware, NJ, U.~.A.).
MULTIWELLTM culture plates were prepared by adding 2 ml of st-?rili7~1 carrot agar into each well. Twenty five ~ll of each of the compounds at 1, lO, 100, and20 1000 ,ug/ml in acetone was added s~;~.al~Lt;ly to the surface of the agar in each well.
In the case of the controls, 25 ~11 acetone was added. All the MULTIWELLTM
plates were kept in a laminar flow hood for two mintlt~s to allow the acetone toevaporate. Each agar well was then individually inoc~ tecl with S mm agar plugs of P. tremulae, O.crassivaginatum, and O. piliferum. The MULTIWELL~M plates 25 were then wrapped with parafilm and inrllb~t~d at 22~C in the dark. The colony diameter was measured and mycelia were observed under a microscope.

The same method was used to screen for inhibition of Marasmius oreades W O 97148279 PCT~B97~0750 except the agar was malt extract agar.

Many of these compounds also may have antibacterial or other ~ntimicrobial activity. The breadth of each compound's activity can be ~l~t~rmin~d using a similar assay. For testing other fungi, b~-t~ or other microbes the same5 procedure can be used, but the nl~tri~nt media used will be based on the nlltrient requirements of the u~ ll to be tested. Some examples include blood agar plates, nutrient agar or another media or agar selected based on the organism being screened. An individual skilled in the art would be famili~r with which agar or media is suitable for a specific organism for this assay.

B. Aspen wood chips Two hundred grams of aspen wood chips were soaked in water in each of seventy-six 250 ml flaslcs. After one hour excess of water was drained and the flasks were autoclaved for one hour at 121~C. When the wood chips were cooled, the flasks were treated s~aLely with S ml of 1, 10, and 100 ,ug/ml ofthe most active compounds listed in Table 1, namely: la, 2, 4b, 7, 8c, and 8f, and then inoculated separately with P tremulae, O. crassivaginatum, and O. piliferum. Four flasks were used for each tre~tm~tlt In the case of the controls, flasks were treated with 2 ml sterile distilled water and five sterile agar plugs without inoculum. The flasks were kept in the inrub~tor in the dark at 22~C and were shaken periodically 20 to fragment the growing mycelia in the wood chips. After 60 days of incubation, wood chips were removed from flasks and photographed. The ~ u...ical structures of the wood chips were also studied by fixing wood chips in formalin-acetic acid-ethanol (FAA). After ten days, the chips were rinsed with 50% ethanol, dehydrated through a n-butanol series under vacuum, and infiltered with 25 PARAPLAST X-TRATM (Monoject Scientific, St. Louis, Missouri) under vacuum at ~6~C. Transverse and radial or tangential sections were made using a rotary microtome. The sections were then observed under a microscope. Data were W O 97/48279 PCTAB97/007~0 subjected to analysis of variance. The individual means were conlL,~ed using Scheffe's test for nnllltirle co~ on using SAS so~ware (S~S Tn~itllte ~nc.
1990).

A visual ~ses~m~nt of colony growth can also be perforrned and used as an indicator of the potency of a colllp~ d. Table 3 ~1lllllll~l ;~es the effects of some congeners of 4-phenyl-3-butenoic acid on col~ni7~ti~-n of aspen chips by P.
tremulae, O. crassivaginatum and O. piliferum.

Toxicity The toxicity of many of these compounds is relatively iow, for examp}e 1 0 senecioic acid has an LD5D intr~g~trically of 3130 mg/kg in rats (Chemical Abstracts 103, 33135w; Gurova, A.I., Smolyar, N.Y., Dr~7h7hin~ N.A., Gig. Tr.
Prof. Zabol. 1985 et al, 1985) and tiglic acid has an LDfr (Amount of chemical ingested during the Food Reduction test which killed or did not kill more than 50% of the test mice) equal to 1150 mg/kg/day (Chemical Abstracts 103: 1655) or 1 5 LD50 equals 111 mg/kg acute oral toxicity (Chemical abstracts 99:65537).

Other org~ni~
Some of these compounds have antibacterial activity or inhibit the growth of other microor~;~ni~m~, for example, senecioic acid inhibits Clostridium botulinum (Hnht~nen et al, 1985).

The same procedures described above can be used to test the activit,v of the present compounds against other microorg~ni~m~ (including other fungi of interest) or other types of wood including hardwoods or softwoods, conifers or deciduous trees.

W 097/48279 PCT~B97/00750 Example ~. Activity against aspen decay and stain fun~
A. Co..~ of 4-phenyl -3-hutenoic acid (Table 1) Thirty eight compounds related to 4-phenyl-3-butenoic acid were tested against P. tremulae, O.crassivaginatum, and O. piliferum and varied inhibition of these fimgi was observed. E4-Phenyl-3-butenoic acid (la3, E4-(1-naphthyl)-3-butenoic acid (le), 4-phenyl-3 -butynoic acid (2), 4-cyclohexylbutanoic acid (4b), ph~l~yl~ noic acid (7), 3-cycloh~yl~opalloic acid (8c), 3-(3-indolyl)propanoic acid (8~, cyclok~ c~. boxylic acid (13), cyclohexylacetic acid (14), pt?nt~ lorophenol (16), copper 8-oxyquinolinate (18), and the zinc salt of 10-llntl~-c~noic acid (~9) completely inhibited the in vitro growth of P. tremulae at 100 and 1000 llg/ml (Table 1). Except for compounds le, 7, and 19, the other nine compounds were inhibitory to P. tremulae even at 1 llg/ml.

Compounds If, 8a, and lS showed inhibition of P. tremulae only at 1000 llg/ml, while the ~ ;llg 22 compounds were inact*e.

For O. crassivaginatum, compounds 2, 4b, 8c, 8f, 14, 16, and 18 were highly toxic and showed an inhibitory effect even at 1 llg/ml. Compounds 7,13, and 19 did not show any inhibitory effect against O. crassivaginatum at 1 ,ug/ml, however, at 10-1000 llg/ml the growth was signific~ntIy reduced. The acids la, le, 9a, and 9b showed inhibitory effect against O. crassivaginatum at 100-1000 ~lg/ml.
The acids lf and 6d showed growth reduction by 25% and 18%, respectively, at 1000 ,ug/ml. The rem~inin~ 22 col.~oullds did not show any inhibitory effect against O. crassivaginatum (Table 1).

For O. piliferum, compounds 2,13, and 14, as well as compounds 16, 18, and 19 completely inhibited the in vitro growth at 10 ~g/ml, while co.l.3.oullds la, 4a, 4b, 8a, and 8c were inhibitory at 1-1000 ~lglml. The acids le, 6a, 7, 8~, and sorbic acid (9a) inhibited the growth of O. piliferum at 100 to 1000 llg/ml. Therem~ining 22 compounds did not show any inhibition at 1-1000 ,ug/ml.

W O 97/48279 PCT~B97/00750 Six of the most active compounds, namely la, 2, 4b, 7, 8c, and 8f, were chosen for tre~tmen1 of aspen wood chips. The organic co-solvent used for these expe~ IG-ll~ was acetone. All six compounds prevented colonization of aspen by P.
tremulae, O. crassivaginatum, and O. piliferum even at 10 llg/ml (Table 3).

P. tremulae is a serious pathogen causing ~2~LeI~si~e decay of aspen.
Previously, the inventors reported growth inhibition of P. tremulae by the metabolites of an antagonistic fimgus Peniophora polygonia (Per.:Fr.) Boud. et Galzin (Trifonov et al. 1992). The redIlctinn of growth and colonization of aspen wood chips by blue stain fungi (O. crassivaginatum and O. piliferum) was also observed when treated with metabolites of the antagonistic hypomyceteous fungi Lecythophora hoffmannii (van Beyma) W. Gams and McGinnis, Stachybotrys cylindrospora C.N.Jensen, and Sporormiella similis Khan and Cain (HildL~ d et al. 1994, Chahav~Ly and Hiratsuka 1994, and Chahdv~ly et al. 19943.

Growth of P. tremulae, O. crassivaginatum, and O. piliferum is significant}y reduced when these are treated with congeners of the enzyme inhibitor 4-phenyl-3-butenoic acid (la).

Of the compounds which retain the chain length of the lead compound la (group C4) the naphthyl analog le showed coll.p~dble activity against P.
tremulae. 4-Cyclohexylbutanoic acid 14b~, which is the product of complete reduction of la, showed the same activity against P. tremulae as la, and was also very active against the blue-stain fungi. The most active product in the C4 group of derivatives is 4-phenyl-3-butynoic acid (2), which inhibited the growth of all three fungi by appro~im~tely 50% at 1 ,ug/ml and by 100% at 10 ~Lglml, thus proving tobe a more active and more general fimgicide than la. The methyl ester of la, thederivatives with para-bromo (lc) or methoxy (Id) substit~ nt~> as well as the cyclo~.Iopa~le analog ~ were completely inactive even at the highest concentration tested (Table l).

W O 97~48279 PCT~B97/00750 The chain shortening of la leading to group C3 was less effective. Only the acids with a triple bond (7), cyclohexyl (8c), or 3-indolyl (8f) substituent exhibited activity comparable to that of la.

The chain elongation (group C5) proved to be least effective. Sorbic acid (ga) and its phenyl analog 9b showed only a weak inhibition of O.
crassivaginatum and O. piliferum. Lauric acid (17), although lcnown as filngici~(Byrde, 1969), showed no activity against the three fu~gi even at 1000 ~lg/ml.
Cyclohe~necarboxylic acid (13~ and especially cyclohexylacetic acid (14) were the most active of the compounds tested. The latter inhibited the growth of all three fungi by at least 50% at I ,uglml and is superior to pentachlorophenol against P.
tremulae.

The activity of these congeners was co~ ~kd with the activity of the known fungicides pentachlorophenol (16), copper 8-oxyquinolinate (18), and the zinc salt of 10-~1n~lec~noic acid (19). Several of the compounds tested showed activity similar to that of the cornmercial filngicidçs The high toxicity and pereiet~nce of pentachlorophenol in the en-vho~ cnt for a long period of time has resulted in its withdrawal from the mar~et. The copper complex 18 and the zinc salt 19 have sirnilar characteristics. Our results show that some of the congeners of the enzyme inhibitor la can be used to control P. tremulae, O. crassivaginatum, and O. piliferum since their efficacy is very similar to that of pentachlorophenol.
These congeners are less toxic, do not contain heavy metals or covalently bound chlorine, and do not persist in the ellvilullllle~lt as does pentachlorophenol, which makes them good candidates for use as antifungal agen~s.

B. D~ ali~es of tiglic acid and senecioic acid (Table 2) Twenty seven compounds which are related to tiglic acid or senecioic acid were tested against P tremulae, O. crassivaginatum, and O. piliferum. The growth W 097/48279 PCT~B97/00750 of P. tremu/ae was completely inhibited by tiglic acid (20), and the cyclic analogs 31 and 32 at 10 ,ug/ml. Of the p-substituted seneciophenones the methyl derivative 26d showed the highest activity - complete inhibition at 100 llg/ml and 47%
inhibition at 10 ~lg/ml. The ie~t~ g seneciophenones 26~,h~c~ç,f and g, the ~mmorlium salts 21d,e, the wood preservative 22, phenyl senecioate (24), p-methylacrylophenon~ (28), and compound 29 showed moderate activity at concentrations 1-1000 llg/ml, while the rlom~inin~ compounds were inactive.

Tiglic acid (20), senecioic acid (21a), and their cyclohexyl analogs 31 and 32 were the most active compounds against O. crassivaginatum (complete inhibition at 10 ~g/ml), followed by the 4~t~ mmonium salt 21e, the substituted seneciophenones 26d,f, and p-methylacrylophenone (28), which had the same efficacy at lO0 llg/ml. Compounds 22, 24, 26c, 26e, and 29 were weakly active at lO0-1000 ,ug/ml, while the rem~ining co~ ou~lds were inactive.

For O. piliferum 100% inhibition was observed with the parent acids 20 and 1 5 21a, with the substituted seneciophenones 26b,c,f, as well as with compounds 31 and 32 at lO ,ug/ml. For p-methylseneciophenone (26d) the inhibition concentration was 100 ~g/ml, while conl~ou~lds 21d, 21e, 22, 24, 26a, 26e, 26g, and 28 exhibited weaker activity at concentrations 1-1000 ~lg/ml. The metal salts 21b, 21c, benzophenone oxime (23a), its ester 23b, the senecioic acid amides 25a, 25b, 25c, the Mannich base 27, as well as colll~ounds 29 and 30 were completely inactive at 1000 ~lg/ml.

The most active compounds reported in Table 2 include the acids 20, 21a, 31, and 32 (against all three fiungi), and the p-sllb~l;L~-Ie~1 seneciophenones 26d and ~6f (against the blue stain fungi O. crassivaginatum and O. piliferum), and 26b (against O. piliferum) which show efficacy superior to tbat of the commercial fungicides 22 and 23a. In addition the above compounds have a low ms-mm~ n toxicity (Gurova et al. 1985) which makes them good candidates for chemiç~l =

W O 97/48279 PCTnB97/00750 protection of aspen wood.

Example 6. Activity against conifer decay and stain fungi (Tables 4 and 5~
Selected most active against aspen pathogens compounds showed varied inhibitory effect on the in vitro growth of two conifer decay fungi Haematostereum sanguinolentum and Phellinus pini. The most active compounds against ~1:
sanguinolentum were la, 4b, 8c, 14, 20, 21a, 22, and 26b (Table 4). Complete inhibition at 100 llglml was observed for 8c, while la, 4b, 14, 20, 21a, 26b, and the commçrcial fim~ici~e 22 showed 45-65% inhibition at this concentration. For 1 O P. pini only compounds 4b, 8c, 8f, 20, and 21a showed activity comparable to that of the cornmercial fungicide 18 (Table 4). These compounds were also inhibitory against two species of conifer blue stain fungi Ophiostoma clavigerum and 0. ips.
For 0. clavigerum the growth was completely arrested by compounds la, 14, 18, and 22 at 100 ,ug/ml, while 4b, 8c, 8f, 20, and 21a, showed 50-80% inhibition atthe same concentration. For 0. ips compounds la and 8c (10û% inhibition at 100 ,ugtml), as well as 4b, 14, 20, and 21a (25-75% inhibition at the same concentration) were superior to the commercial fungicides 18 and 22 (Table 5).

lh.Y~lnrle 7. Activity against fairy ring fungus Mur~~,.i~ oreades (Tables 6 and 7) Several of the compounds described in Tables 1 and 2 were also tested against the fairy ring fungus Marasmius oreades (Table 6). Of the compounds tested for their ability to inhibit the growth of Marasmius oreades the most potent inhibitors were structures la, 21a, 14, 13, 32, 8f, and 35. Structures 19 and 26d were also inhibitory but for this o~ sln they were not as potent.

Combinations of compounds were also tested for their ability to ;nhibit Marasmius oreades (Table 7). The combinations of equal amounts of benzoic acid W O 97/48279 PCT~B97/00750 (35) with la, 21a, 13, 14 or 8f resulted in the inhibition of growth more than or equal to the inhibition of la, 21a, ~3, 14 or 8f alone and significantly more inhibition than 35 alone. There was a potentiation observed when the compounds were combined~

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. .

W 097/48279 PCT~B97/00750 Sow,~ .,..., D., Prasad, KJ., 1985, Allllllillilllll chloride/phosphoryl chloride as an efflcient acylating compound, Synthesis, 545-546.
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~o--W O 97/48279 PCT~B97/00750 Table 7: Effect of Benzoic acid alone and in cQ~ t~ with other compounds on the in r~ro growfh of MUr~~ L~S oreades Co~l~uul.d name cQl~re~ n (,ug/mL)~

la ~Phenyl-3-butenoic acid 25c 35b lOOa lOOa lOOa lOOa lOOa +35 ~ Benzoic acid 21a Senecioic ~id 45c 65b lOOa lOQa lOOa lOOa lOOa +35 + Benzoic acid 14 Cyclohexylacetic acid lSd 45c 68b lOOa lOOa lOOa lOOa +35 + Benzoic ~id 13 Cyrloh.ox~,.r~ ~,boxylic acid lOe 21d 45c 75b lOOa lOOa lOOa +35 + Benzoic acid 8f 3-(3-Indolyl)propanoic acid 35d 65c 75b lOOa lOOa lOOa lOOa +35 ~ Benzoic acid la ~Phenyl-3-butenoic acid 14c 65b lOOa lOOa lOOa lOOa lOOa 21a Senecioic acid 37c 75b lOOa lOOa lOOa lOOa lOOa 14 Cyclohexylacetic acid 13c 35b 35b lOOa lOOa lOOa lOOa 13 Cy~loh~-x~.~rc;1,bo,~ylic acid Sd lOc llc 75b lOOa lOOa lOOa 8f 3-(3-Indolyl)propanoic acid 20e SOd 56c 88b lOOa lOOa lOOa Benzoic acid - - lSc 4~b lOOa lOOa lOOa ' Values are means of 10 replicates. Data analyzed by one-way ANOVA and Scheffe's test for multiple coll~L)~ison after Arscine Transforrnation. Values in each row followed by the same letter do not differ significantly (P=0.05).
Concentrations refer to that of the ~lrst coll~u..ent in the two component mixtures.
Benzoic acid is added in equal amounts.
The media was malt extract.

Claims

We claim:
An antifungal composition at least compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R' is selected from the group consisting of (1) H,(2) C1-C15 alkyl,(3) a group wherein R7 and R8 are C1-CI5 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;

R2 through R5 are each independently H or Cl-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of Rl through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R' is only Ar;
R6 is selected from the group consisting of (1) H, (2) Cl-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from Cl-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or l; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl, R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof, and a carrier or diluent therefor.
2. The antifungal composition of claim 1, wherein the at least one compound is of formula III

wherein R13 through R15 are each independently H or C1-C15 alkyl, or two of R13 through R15, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring; and R6 is as defined above.
3. The antifungal composition of claim 1, wherein the at least one compound is of formula IV

wherein R6 through R8 and n are as defined above.
4. The antifungal composition of claim 1, wherein the at least one compound is of formula V

wherein R16 is a group Ar, wherein Ar is as defined above;

R17 through R20 are each H, or R17 and R18 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R17 and R18 together, and R19 and R20 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound;
R21 is selected from the group consisting of (1) H,(2) C1-C15 alkyl, (3) a group N(CH3)2(C10H21)2, (4) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (5) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4; and n is as defined above.
5. The antifungal composition of claim 1, wherein the composition comprises at least one compound of formula II, wherein R9 through R12 are as defined above.
6. The antifungal composition of claim 1, wherein the composition comprises at least one compound selected from the group consisting of:
E-4-phenyl-3-butenoic acid, E-4-(1-naphthyl)-3-butenoic acid, E-4-(2-naphtnyl)-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-phenylbutanoic acid, 4-cyclohexylbutanoic acid, E-cinnamic acid, E-4-hydroxy-3-methoxycinnamic acid, phenylpropynoic acid, hydrocinnamic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, sorbic acid, E,E-5-phenyl-2-4-pentadienoic acid, 5-phenylpentanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, phomalone, isobutyric acid, isovaleric acid, tiglic acid, senecioic acid, p-benzoquinone dioxime, phenyl senecioate, N-senecioylanthranilic acid, seneciophenone, p-hydroxyseneciophenone, p-methoxyseneciophenone, p-methylseneciophenone, p-isopropylseneciophenone,2,4-dihydroxyseneciophenone, 2-hydroxy-4-methoxyseneciophenone, p-methylacrylophenone,3-(2-furyl)-4'-methylacrylophenone, cyclohexene-1-carboxylic acid and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
7. The antifungal composition of claim 6, wherein the composition comprises at least one compound selected from the group consisting of:
E-4-phenyl-3-butenoic acid, E-4-(1-naphthyl)-3-butenoic acid, E-4-(2-naphthyl)-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-phenylbutanoic acid, 4-cyclohexylbutanoic acid, phenylpropynoic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, 5-phenylpentanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, isobutyric acid, isovaleric acid, tiglic acid, senecioic acid, p-hydroxyseneciophenone, p-methoxyseneciophenone,p-methylseneciophenone, 2,4-dihydroxyseneciophenone, p-methylacrylophenone, cyclohexene-1-carboxylic acid and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
8. The antifungal composition of claim 6, wherein the composition comprises at least one compound selected from the group consisting of:
E-4-phenyl-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-cyclohexylbutanoic acid, phenylpropynoic acid, 3-cyclohexylpropanoic acid and 3-(3-indolyl)propanoic acid, or an alkali or alkali earth salt thereof.
9. The antifungal composition of claim 1, further comprising benzoic acid.
10. The antifungal composition of claim 1, further comprising salicylic acid.
11. The antifungal composition of claim 6, further comprising benzoic acid.
12. The antifungal composition of claim 11, wherein the compound is selected from the group consisting of E-4-phenyl-3-butenoic acid, 3-(3-indolyl)propanoic acid, cyclohexanecarboxylic acid and cyclohexylacetic acid, or an alkali or alkali earth salt thereof.
13. The antifungal composition of claim 1, wherein the group Ar is selected from the group consisting of , , and
14. A method of reducing or inhibiting fungal growth in a region to be treated, comprising applying to the region a fungal reducing- or inhibiting-effective amount of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1)H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2,(5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
15. The method of claim 14, wherein the at least one compound is of formula III

wherein R13 through R15 are each independently H or C1-C15 alkyl, or two of R13 through R15, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring; and R6 is as defined above.
16. The method of claim 14, wherein the at least one compound is of formula IV

wherein R6 through R8 and n are as defined above.
17. The method of claim 14, wherein the at least one compound is of formula V

wherein R16 is a group Ar, wherein Ar is as defined above;
R17 through R20 are each H, or R17 and R18 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R17 and R18 together, and R19 and R20 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound;
R21 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) a group N(CH3)2(C10H21)2, (4) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (5)NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4; and n is as defined above.
18. The method of claim 14, wherein the at least one compound is of formula II, wherein R9 through R12 are as defined above.
19. The method of claim 14, wherein the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, E-4-(1-naphthyl)-3-butenoic acid, E-4-(2-naphthyl)-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-phenylbutanoic acid, 4-cyclohexylbutanoic acid, E-cinnamic acid, E-4-hydroxy-3-methoxycinnamic acid, phenylpropyonic acid, hydrocinnamic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, sorbic acid, E,E-5-phenyl-2,4-pentadienoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, phomalone, isobutyric acid, isovaleric acid, tiglic acid, senecioic acid, phenyl senecioate, N-senecioylanthranilic acid, cyclohexene-1-carboxylic acid, cyclohexylideneacetic acid, seneciophenone, p-hydroxyseneciophenone, p-methoxyseneciophenone, p-methylseneciophenone, p-isopropylseneciophenone, 2,4-dihydroxyseneciophenone, 2-hydroxy-4-methoxyseneciophenone,p-methylacrylophenone,3-(2-furyl)-4'-methylacrylophenone and p-benzoquinone dioxime, or an alkali or alkali earth salt thereof.
20. The method of claim 19, wherein the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-cyclohexylbutanoic acid, phenylpropyonic acid, 3-(3-indolyl)propanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, tiglic acid, senecioic acid, cyclohexene-1-carboxylic acid, cyclohexylideneacetic acid, p-methoxyseneciophenone, p-methylseneciophenone, 2,4-dihydroxyseneciophenone and p-methylacrylophenone, or an alkali or alkali earth salt thereof.
21. The method of claim 14, further comprising contacting benzoic acid with the region, wherein the at least one compound and the benzoic acid are present in amounts to produce a fungal reducing- or inhibiting-effect.
22. The method of claim 21, wherein the benzoic acid and the at least one compound are co-applied.
23. The method of claim 14, wherein the region comprises a plant surface.
24. The method of claim 14, wherein the region comprises a wood surface.
25. The method of claim 14, wherein the region is a soil region having plants thereon.
26. The method of claim 14, wherein the group Ar is selected from the group consisting of , , and
27. A method of reducing or inhibiting at least one of fungal wood decay and fungal wood stain on a wood substrate, comprising applying to the wood substrate at least one of a fungal-decay and fungal-stain reducing- or inhibiting-effective amount of at least one compound selected from the group consisting of:

(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
28. The method of claim 27, wherein the at least one compound is of the formula III

wherein R13 through R15 are each independently H or C1-C15 alkyl, or two of R13 through R15, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring; and R6 is as defined above.
29. The method of claim 27, wherein the at least one compound is of formula IV

wherein R6 through R8 and n are as defined above.
30. The method of claim 27, wherein the at least one compound is of formula V

wherein R16 is a group Ar, wherein Ar is as defined above;
R17 through R20 are each H, or R17 and R18 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R17 and R18 together, and R19 and R20 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound;
R21 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) a group N(CH3)2(C10H21)2, (4) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different (5) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4; and n is as defined above.
31. The method of claim 27, wherein the at least one compound is of formula II, wherein R9 through R12 are as defined above.
32. The method of claim 27, wherein the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-cyclohexylbutanoic acid, phenylpropynoic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, isobutyric acid, isovaleric acid, tiglic acid, senecioic acid, phenyl senecioate, p-hydroxyseneciophenone, p-methoxyseneciophenone, p-methylseneciophenone, 2,4-dihydroxyseneciophenone, p-methylacrylophenone, cyclohexene-1-carboxylic acid and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
33. The method of claim 27, wherein the method is for reducing or inhibiting fungal wood stain and the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-phenylbutanoic acid, 4-cyclohexylbutanoic acid, E-cinnamic acid, phenylpropynoic acid, hydrocinnamic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, sorbic acid, E,E-5-phenyl-2,4-pentadienoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, tiglic acid, senecioic acid, phenyl senecioate, p-hydroxyseneciophenone, p- methoxyseneciophenone, p-methylseneciophenone, 2,4-dihydroxyseneciophenone, p-methylacrylophenone, cyclohexene-1-carboxylic acid and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
34. The method of claim 27, wherein the method is for reducing or inhibiting fungal wood decay and the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, E-4-(1-naphthyl)-3-butenoic acid, 4-phenyl-3-butynoic acid, 4-cyclohexylbutanoic acid, phenylpropynoic acid, 3-cyclohexylpropanoic acid, 3-(3-indolyl)propanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, phomalone, isobutyric acid, isovaleric acid, tiglic acid, senecioic acid, phenyl senecioate, N-senecioylanthranilic acid, p-methoxyseneciophenone, p-methylseneciophenone, 2,4-dihydroxyseneciophenone, 2-hydroxy-4-methoxyseneciophenone, p-methylacrylophenone, cyclohexene-l-carboxylic acid and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
35. The method of claim 27, wherein the group Ar is selected from the group consisting of , , and
36. A method of reducing or inhibiting fairy rings in a region to be treated, comprising applying to the region a fairy-ring fungal reducing- or inhibiting-effective amount of at least one compound selected from the group consisting of:

(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1)H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n'is 0 or l; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
37. The method of claim 36, wherein the at least one compound is of the formula III

wherein R13 through R15 are each independently H or C1-C15 alkyl, or two of R13 through R15, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring; and R6 is as defined above.
38. The method of claim 36, wherein the at least one compound is of formula IV

wherein R6 through R8 and n are as defined above.
39. The method of claim 36, wherein the at least one compound is of formula V

wherein R16 is a group Ar, wherein Ar is as defined above;
R17 through R20 are each H, or R17 and R18 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R17 and R18 together, and R19 and R20 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound;
R21 is selected from the group consisting of (1)H, (2)C1-C15 alkyl, (3) a group N(CH3)2(C10H21)2, (4) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (5) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4; and n is as defined above.
40. The method of claim 36, wherein the at least one compound is of formula II, wherein R9 through R12 are as defined above.
41. The method of claim 36, wherein the at least one compound is selected from the group consisting of:
E-4-phenyl-3-butenoic acid, 3-(3-indolyl)propanoic acid, cyclohexanecarboxylic acid, cyclohexylacetic acid, senecioic acid, p-methylseneciophenone and cyclohexylideneacetic acid, or an alkali or alkali earth salt thereof.
42. The method of claim 36, further comprising contacting benzoic acid with the region, wherein the at least one compound and the benzoic acid are present in amounts to produce a fairy-ring fungal reducing- or inhibiting-effect.
43. The method of claim 42, wherein the benzoic acid and the at least one compound are co-applied.
44. The method of claim 36, wherein the group Ar is selected from the group consisting of , , and
45. A paint containing at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group .

wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
46. A stain containing at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C16 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar, R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1, and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH, and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
47. A cleaning product containing at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring, R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m , wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R1 is other than phenyl, n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH, and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
48. A disinfectant containing at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m , wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
49. A wood or lawn treatment containing at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof.
50. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m , wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an active ingredient in the preparation of an antifungal composition.
51. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar, R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H12)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl, n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH, and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an ingredient in the preparation of a paint.
52. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R3 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4.m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1, and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an ingredient in the preparation of a stain.
53. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar, R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an ingredient in the preparation of a cleaning product.
54. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring, R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar, R5 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH, and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an ingredient in the preparation of a disinfectant.
55. Use of at least one compound selected from the group consisting of:
(a) at least one compound of formula I

wherein R1 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) a group wherein R7 and R8 are C1-C15 alkyl or, together with the carbon atoms to which they are bound, form a 3-8 membered carbocyclic ring, and (4) a group Ar, wherein Ar is an aromatic ring;
R2 through R5 are each independently H or C1-C15 alkyl, or R2 and R3 together are a bond thus creating a double bond between the carbon atoms to which they are bound, or R2 and R3 together, and R4 and R5 together, are bonds thus creating a triple bond between the carbon atoms to which they are bound, or two of R1 through R5, together with the carbon atoms to which they are bound, form part of a 3-8 membered carbocyclic ring, with the proviso that when R2 through R5 are each H, then R1 is only Ar;
R6 is selected from the group consisting of (1) H, (2) C1-C15 alkyl, (3) phenyl, (4) a group N(CH3)2(C10H21)2, (5) a group N(C1-C15 alkyl)4, wherein the alkyl groups are the same or different, (6) NHm(X)4-m, wherein each X is independently selected from C1-C15 alkyl and 2-hydroxyethyl, and m is 0-4, with the proviso that when R1 is Ar, then R6 is other than phenyl;
n is 0-10 and n' is 0 or 1; and (b) at least one compound of formula II

wherein R9 is selected from the group consisting of H, OH and C1-C15 alkyl;
R10 is H or OH; and R11 and R12 are each independently H or C1-C15 alkyl, or an alkali or alkali earth salt thereof as an ingredient in the preparation of a wood or law. treatment