CA1171866A - Phenyl triazole ethanols and their use as fungicides - Google Patents

Abstract

Abstract of the Disclosure Novel phenyl triacole compounds are described of the general formula I, I
They are useful as fumalcides.

Description

I 1 71~
Case 136-6878 The present invention relates to a-aryl-lH-1,2,4-triazole-l-ethanols, more particularly a-alkyl-~-phenyl-lH-1,2,4-triazole-l-ethanols, their use as fungicides and agricultural compositions for facilitating such use.
More specifically, the present invention provides compounds of formula I, R~ OH ~=~N
C - CH -N J
R~

wherein R is alkyl of l to 12 carbon atoms, cyclo-alkyl of 3 to 8 carbon atoms or cyclo-alkylalkyl of 4 to ll carbon atoms in which the cycloalkyl portion is of 3 to 8 earbon atoms and the alkyl portion of 1 to 3 earbon atoms, said eycloalkyl and eyeloalkylalkyl aroups being optionally substituted by one or two alkyl group~
of 1 to 3 carbon atoms, R is hydrogen, halogen having an atomic number of from 9 to 35, alkyl of l to 4 earbon atoms, mono-, di- or tri-halo-alkyl of l to 4 earbon atoms in whieh the halo is independent].y an halogen ha~ing an atomie number of from 9 to 35, alkoxy of l to 4 earbon atoms, alkylthio ~ ~.

' 17186~

- 2 - 13~-687 of 1 to 4 carbon atoms, or nitro, and R' is hydrogen, halogen having an atomic number of from 9 to 53, alkyl of 1 to 4 carbon atoms, mono-, di- or tri-halo-alkyl of 1 to 4 carbon atoms in ~hich the halo is inde~endently an halogen having an atomic number of from 9 to 35, alkoxy of 1 to 4 carbon atoms, mono-, di or tri-haloalkoxy of 1 to 4 carbon atoms in which the halo i5 independently an halogen having an atomic number of from 9 to 35, alkylthio of 1 to 4 carbon atoms, nitro, -CN, -COOR", Y

Y or yO
- Z~

R" is hydroyen, alkyl of 1 to 4 carbon atoms, R"' is hydrogen, an halogen having an atomic number of from 9 to 17 or alkyl of 1 or 2 carbon atoms, Z is oxygen or sulfur, or R and R' together represent alkylenedloxy o 1 or 2 carbon atoms substituted onto a.djacent carbon atoms of the phenyl ~ing A, and ~ 17186B

- 3 - 136-6878 Y and Y are independently hydrogen, halo~en having an atomic number of from 9 to 35, alkyl of 1 to 4 carbon atoms or a].koxy of 1 to 4 carbon atoms.
Halogen atoms having an atom.ic number of from 9 to 53 are fluoro, chloro, bromo and iodo, such having an atomic number of from 9 to 35 are fluoro, chloro, bromo and those having an atomic number of from 9 to 17 are fluoro and chloro.
When any R or R' is or includes mono-, di- or tri-haloalkyl this is e.g. CF3 The invention also provide~s processes for the production of compounds of formula I comprising a) reacting a compound of the formula II:
H2C~
R ~ / O II

R' ~ CRo R"' wherein R, R, R' and R"' are as above defined, with a compound of forrnula III

X-N III
~-wherein X is an alkali metal in an inert organic solvent, b) obtaini.ng a compound of forrnula Ia, ' ~71866

- 4 - 136-6878 R ~ , 2 ~N ~ Ia HOOC R
wherein R and R are as defined above by oxidation of the CH3 group of a compound of formula Ib, R ~ C - CH2 - N ~ Ib wherein R and R are as defined above, or c) obtaining a compound of formula Ic, AlkOOC ~ C - CH2 - N ~ Ic where1.n R and R are as defined above and 1~11. i~ Cl_ 4alkyl, by esterification of a compound of formula Ia ~1ith an alcohol. of formula IV
Alk-OH IV

wherein Alk. is as defined above, or a reactive nctional derivative the~eof.
The process a) may be carried out at temperatures typically fxor.l 0C to 1.80, preferably ~0C to 120C, in an inert organic solvent of conventional type, e.g. an amide of an oxganic carboxylic acid such as dimethyl-forrnamide. ~s is conventional, the compound of the forrnula III is preferably prGvided by reacting tr.ia~ole with a strong base such as an alkaii metal hydride e.g.
sodil1m hydride, in an inert organic solvent which is - -`` ! 171866 conveniently the same solvent which is to be used in process a).
The oxidation according to process b) may be carried out with the aid of oxidizing agent capable of oxidizing an CH3-group to a COOH group. Suitable oxidizing agents are potassium permanganate, manganese dioxide and the like, preferably potassium permanganate. The reaction is conven-iently carried out in aqueous solution. A suitable reaction temperature for process b) is from 20 to 150C, preferably from 60 to 120C.
The compounds of formula Ia are depending on the reaction conditions and the recovery steps obtained in free form or in salt form (H of- COOH substituted by a cation). Free forms of compounds of formula Ia may be converted into salt forms in conventional manner and vice versa. The cation of the salt form of compounds of formula Ia is preferably an agriculturally acceptable cation such as Na , K and NH4 The process c) may be carried out in accordance with known esterification procedures for compounds containing a potentially reactive hydroxyl group. The esterification with an alcohol of formula IV is conveniently carried out at a reaction temperature of from 30C to 80C, advant-ageously under anhydrous conditions and in the presence of an acid, such as hydrogen chloride. Suitable solvents for this reaction are inert organic solvents or an excess of the alcohol of formula IV.

~ 171S~66 - 5a -Suitable reactive functional derivatives of an alcohol of formula IV are the corresponding diazoalkane, e.g. a diazoalkane of 1 to 3 carbon atoms, or an alkylhalide, particularly a chloride, bromide or iodide. The reaction with a diazoalkane is conveniently carried out under anhy-drous conditions in an inert organic solvent. A suitable reaction temperature is then -20C to +40C, more usually -5C to +20C. For the reaction with an alkylhalide the compounds of formula Ia are preferably in salt form, e.g.
the alkali metal and silver salt form. Such reaction is conveniently carried out in an inert organic solvent at temperatures of from 0C to 100C, more usually 40C to 90C .
The reaction product of processes a), b) and c) may be recovered from the reaction mixture in which it is formed by working up by established procedures.
The compounds of formula I wherein R' is other than COOH may be prepared and used in the form of acid addition - salt forms. The compounds of formula I are ethanol deriva-tives and can therefore exist in free form and in alternate forms such as an ethanolate salt form, e.g. a sodium ethanolate form, and in metal complex form, e.g. of metals from the groups Ib, IIa, IIb, VIb, VIIb and VIII of the periodic table, such as copper and zinc, and with anions such as chloride, sulphate, nitrate, carbonate, acetate, citrate, dimethyldithiocarbamate and the like.

J 171~66 Any salt form of compounds of formula I is preferably in the form of an agriculturally acceptable salt form.
The acid addition salt forms, the ethanolate salt form and the metal complex form can be prepared from the corres-ponding free form in conventional manner and vice versa.
The compounds of formula II may be prepared byreacting a compound of the formula V

R
~ R"' V

R - C = O
wherein R, R, R' and R"' are as above defined, with 10 the reaction productof a strong base andtrimeJchy]sulfonium iodide which provides a rea~ent which may be repre~ented by the formula VI

CH 1~ CH e VI

which process is carrled out in an inert organic 15 solvent. This process is a known type reaction for the - preparation of epoxy derivatives from ketones.
Many of the compounds of the formula V are kno~7n and those whlch are not known E~ se may be prepa~red f~om known ~aterials b~ procedures analogous to those 20 known for preparation of the known compounds. Ilany of the compounds II are also known.

~ 171866 The compounds of the formula I are useful as fungi-cides in combatting phytophathogenic fungi including particularly powdery mildews and rust fun~i, as indicated by standard in vivo and in vitro tests of the type hereinafter illustrated. ~or such use the compounds of .he formula I may be applied to plants seed or ~oil in a manner conventional in the use of fungicidal agents.
As will be appreciated, the amount of the compound of the formula I to be applied will vary depending upon Xnown factors such as the particular compound employed, whether the treatment is prophylactic or therapeutic whether the compound is applied as a foliar spray, a ~oil treatment or a seed dressing, the species of fungus under treatment and the time of application. Ilowever, in general, satisfactory re~sults are obtained when the compound is applied to a crop locus, either on crops or to 5011, at a rate of from about O.OOS to 2, preferably about 0.01 to 1 kg (active ingredient)/hectare. The treatment may be repeated as required, e.g. at 8 to 30 day intervals. When employed as a seed dressing, satis-factory results are obtained when the compound is employed at a rate of irom about O.OS to O.S, preferab].y about 0.1 to 0.~ g/]cg seed.
The term 'soil' a~ used herein is intended to embrace any conventional growing medium whether natural or artiflcial.

.

1 ~71866 The invention also provides, as an additional feature, fungicidal compositions, comprising, as fungi-cide, a compound of for~.ula I in free fo~m or in agriculturally acceptable salt form and an inert fungicide carrier or diluent. In general, such composi-tions contain from about O.OC05 to 9o, preferably from about 0.1 to 50% by wei~ht of active agent. They may be in concentrate form, for dilution down prior to appli-cation, or in dilute, ready ~o apply, form. As examples of particular form~ may be given wettable powder, emulsion concentrate, dusting, spraying, granulate and delayed release forms~ incorporating conventional carriers and sucn other diluents and/or adjuvants acceptable in the agricultural art. Application ~orms of those compositions generally contain between about 0.0005 and 10~ by .~eight of a compound of formula I as active agent. Typical spray suspensions may contain, for example, from 0.0005% to 0.05%, preferably 0.001~ to 0.02 by ~Jeight of active ingredient. Concentrate forms of composition~ for fungicide use generally contain bet~een about 2 and 90%, preferably between about 5 and 70%, by weight of a compound of formula I as active agent.
Emulsion concentrate forms aenerally contain from about 10 to 70%, preferably about 20 to 60% by welyht of active ingredient. Solid, particulate composltions are preferred.
The compositions particularly adapted for spraying preferably include a surfactant swch as a liquid ooly-- ` ' 171866 - 9 - 136-~878 glycol ether, a fatty alkyl sulphate or a lignin sulpho-nate.
In addition to conventional caxrier and surface-active materials, formulations of the compound I of the invention may also contain further additives with special purposes e.g. stabilizers, deactivators (for solid f~rmu-lations on carriers with an active surface), agents for improving the adhesion to plants, corrosion inhibi~ors, anti-foaming agents and colorants.
Moreover, further fungicides, bactericides or other beneficially-acting materials, such as insecticides, may be present in the formulations and are contemlated as further er~odiments of this invention.
Exarnples of the production of fungicide formulations are as follows:
a) Wettable_e_wder formulation 50 part~ of a compound of formula I, e.g~ ~-t-butyl-a-(p-methylphenyl)-1~1-1,2,4-triazole-1-(?,thanol are ground with 2 parts of lauryl sulphate, 3 parts sodium lignln sulphonate and 45 parts of finely divided kaolinite until the mean particle size is below 5 microns. The resulting spray liquor may be applied bv foliar spray as ~Jell as hy root drench application.
b) Granulat,e formulat _n 25, Onto 94.5 parts by wei~ht of quartz sanci in a tumhler mixer i9 sprayed 0.5 parts by ~leiaht of a binder (non-ionic tensi.de) and the whol,e thoroughly mi~:ed. 5 Parts ~ 171866 - 10 - ~36-6878 by weight of a compound of formula I, e.g. powdered ~-t butyl-a-(p-methylphenyl)-lH-1,2,4-triazole-1-ethanol are then added and thorough mixing con~inued to obtain a granulate formulation with a particle size in the range of from 0.3 to 0.7 mm. The granulate may be applied by incorporation into the soil adjacent the p]ants to be treated.
c) Emulsion Concentrate . _ .
25 Parts by weiaht of a compound of formula I, e.g.
a-t~-butyl-a-(p~methylphenyl)-1~-1,2,4-triazole-1 ethanol are mixed with 30 parts by weight of iso-octyl phenyl octaglycol ether and 45 parts by weight of a petroleum fraction with a boiling ranse of 210-280C (D2o:0.92).
The concentrate is diluted with water to the desired concentration.
d) Seed dres~
45 Parts of a compound of a compound of formula I, e.g.
~-t-butyl-a-(p-methylphenyl)-lH-1,2,4-triazole~l-ethanol are mixed with 1.5 parts of diamyl phenoldecaglycolether 20 ethylene oxide adduct, 2 parts of spindle oil, 51 parts of fine talcum and 0.5 parts of colorant rhodamin B. The mixture is ground in a contraplex mill at 10,000 rpm until an average particle of less than 20 microns is obtained.
The resulting dry seed dressing powder has good adherance 25 and may be applied to seeds, e.g. by mixing for 2 to 5 minutes in a slowly turning vesse].

' ! 1718f66 ~ ,6-6878 Fungi a~ainst which the compounds of the formula I
are indicated to be particularly of interest include by way of illustration i:he following:
A) _ S 1 m~es, comprisi~g S A.l) those of the Order Uredinales such as those of the genus Uromyces in plants such as beans, e.g. Uromyces aE~endicu1atus, and orna~.entals, e.g. UromYces dianthi, those of the genws Hemileia in plants such as coffee, -e.~. Hemileia vastatrix, those of the genus Puccinia in plants such as cereals (e.g. whea~, oats, barley) e.g.
Puccinia graminis, Puccinia recondita and Puccinia striiformis, or ornamentals, e.g. _ccinia ~araonii-zonalis and Pucc. antirrhin , those of the genus Phakopsora in plants such as soya, e.g. Phako~so~a ~ y~ , those of the genus ~ in plants such flax, e.g. ~ llni, and those of the genus ranz~chelia, e.g. ~ranzschella pruni in plums;
A.2) those o the Order IJstilaginales such as those of the ~enus Ust~ in plants such as barley, wheat, corn and sugarcane, e.g. U. maydis on corn and U. nuda on barley, and P..3~ those of the ~enus Stereum in pip and stone fruit ~rees, e.g. Stereum ~ur~ureum in apple and prune.
B) Ascom~_etes, comprislng B,l) those of the Order Erysiphales such as thosn of the genus Ery_~he in plants such as cucumber, barley, ~heat and sugarbeet, e.g. ~r~s~he ~r ~inls f.~. t~itici ! 17t866 on wheat and Erysiphe cichoraceareum on cucumbers; those of the genus Spohaerotheca on cucumbers and roses, e.g.

Spohaerotheca pannosa on roses; those of the genus Podosphaera in apples, pears and prunes, e.g. Podosphaera leucotricha on apples; those of the genus Uncinula on _. .
plants such as grapes, e.g. Uncinula necator on grapevines;
those of the "genus" Oidium on a wide variety of plants;
and those of the genus Leveillula in plants such as cotton and other Malvaceae, e.g. Leveillula taurica on cotton.
C) Oomycetes, comprising C.1) those of the genus Phytophthora spp., e.g. Ph.
cactorum, Ph. parasitica and Ph. cinamomi on susceptible plants; and C.2) those of the genus Aphanomyces in plants such as pea and sugar beet, e.g. Aphanomyces euteiches in sugar beet, and D) Deuteromycetes, comprising D.l) those of the genus Helminthosporium in plants such as barley and corn, e.g. Helm. Sativum;
D.2) those of the genus Septoria in plants such as wheat, tomato and celery, e.g. Sept. tritici in wheat, tomato and celery, e.g. Sept. tritici in wheat;
D.3) those of the genus Rhizoctonia in plants such as cotton and potato, e.g. Rhiz. solani in cotton;
D.4) those of the genus Fusarium spp, e.g. F.oxysporum f. sp. lycopersici in tomato, F. oxysporum f. sp. vasin-fectum in cotton, F. oxysporum f. sp. cubense in banana, ,, -.~
!~, -! 171~66 - 13 - 13~-6~78 F. solani in vegetables, F. culmorum in cereals and F. ~raminearum in cereals;
D.5) those of the genus Thiela~iiopsis in plants such as cotton, tobacco etc., e.g. Th'ielaviopsis'basicola in co~ton;
D.6) those of the genus Phoma in plants such as sugar beet, rape etc., e.g. Phoma betae in suyar beet;
D.7~ those of the genus P icularia spp,, e.g. P.ory~ae - on rice; and D.8) those of the genus Colletotrichum sp~., e.g.
C. lindemuthianum in beans.

The followin~ conventional tests are i].lustrative of the manner by which the fungicidal activity of the ',' compounds of the formula I may be inaicated.
~, 15 'rest Method A: In vivo employing bean rust (Uromyces appendiculatus). Phaseolus vulgaris (pole bcan plant) is cultivated in a mixture of peat and sand in plastic pots ~ of 6 cm diameter for 9 days. The plants are sprayed with " a spray liquor containing 0.0008 to 0.05~ (e.g. at 20 0.0008%, O.OG3~, 0.012~ and 0.05%) active inyredient.
Treatment comprises foliar spraying to near run-of f or soil drenching (28 ml of spray liquor per pot). ~fter , dryi.ng, the plants are inoculated "ith a spore suspension ;, s~ray (S00,~00 to 700,000 spores/ml) and in.,ubated for 7 days in an incubatiQn chamber at 100~ relative humidity and 21. The sfficacy of the active agent treatment is -- g ~71866 determined by comparing the number OL pustulesjleaf with that on untreated, similarly inoculated check plants.
The compounds of formula I, particularly ~he compour~ds of the Examples hereinafter e.g. the co~ ounds of the E~,les

5 1, lA, lB, lC, 2A, 2B, 2D, 2F, 2G, 2I~, 2L, 2N, ~, 2Z-l, 2'Z~3~ 2~-4, 2Z-7, 2Z-8, 2Z-9, 2Z-11, 2Z-13, 2Z-1~, 2Z-15, 2Z-24~ 2Z-27~ 2Z-28 2Z-32, 2Z-33~ 2Z-41t,o 2Z-44 and 3 hereinaf~er used in the wettable powder formulation given above provide a significant degree of funyicidal activity in the above lOtest, botn by contact as well as root-systemic action.
Anzlogous tests are run on the following crc)p/fungi with similar results.
Coffee : cofee leaf rust (Hemileia vas~atrix) Wheat : black stem rust (Puccinja graminis) 15Wheat : bro~n leaf rust (Puccin1a recondita) ~eat : yellow ~r striPe rust (Puccinia strii-forrni,s) Flax : fl.ax rust (Melarns~ora Li.nl) Pelargonlum : Pelargonium rust (Puccinia pelaryonii.-20 ' zonali ) Snapdragon : Sn~pdragon rust (Puc~cinia antirrhin~.).
" Test ethocl B: In vivr) employing cucumber po~ldery mi.ldew ~y~Ehe cichor cearum). Cucumis sati,vus (cucumber) . 1~ cultlvated ln a mi,Y.ture of peat and sand in plastic ', 25pots of 6 cm diarneter for 7 days. The plants are spra~ed with a spray l.iquor contai.nlng 0.0008 to 0.05~ (e.g. at ,0.0008%, 0.(~03~, 0.012~ arld 0.05~,) acti.ve ingre~diellt.
,, 1 ~71 ~fi~

Treatment cornprises foliar spraying ~o near run-off or soil drenching (28 ml of spray liquor per pot). After drying, the plants are inoculated by dusting them with freshly collected conidia and are then incubated for 7 days in an incubation chamber at 60-80% relative humidity and 25-30C. The efficacy of the active ingre-dient is determined by cornparing the degree of fungal attack with that on untreated, similarly inoculated check plants. The compounds of formula I particularly ~he 10 compounds of the examples hereinafter, e.g. the cornpounds of the Examples 1, 2A, 2B, 2C, 2D, 2F, 2G, 2H 2L 2N 2P, 2Q, 2R, 2S 2T, 2U, 2V, 2Z-1 2Z-3 2Z-4, 2Z-6 to 2z-~,-2z-11 2Z-13 to 2Z~15, 2Z-24, 2Z-26, 2Z-27, 2Z-2~, 2Z-35, 2Z-~0 to 2Z-~7, lA, lB, IC and Example 3 hereinafter 15 us~d in the wettable powder formulation given above ~r, provide a significant degree of fungicidal activity, both by contact as well as root-systemic action.

T~sts analogous to Test ~iethod B are made with similar results on the follo-"ing crop/fun~i:
20 Wheat : wheat powdery mildew (Erys. ~m. f.s tritici) Barley : barley powdery mildew (Erys. gram. f.s hordei) Apple : apple powdery mildew (Podos _eu~otr1cha) Grape : grapevi.ne powdery mildew ( ncinula r.ecator) : Test Method B, above, as regards cucumber po-,7dery 25 mildew and the preferred compound of Exarnple 1, herein-after is repeated (both foliar spray and soil drench) but at t}le low~r concentrations 0c 0.0002% and 0.00005~ with the result that 100% control of the fungi is still obtained, thereby still further indicating the remark-able potency provided by the invention. At concentrations of 0.000012% and 0.000003% in the same test a control of 70% and 50%, respectively, is obtained in spray applica-tion and a control of 90% and 70%, respectively in the soil drench application. In repeating Test Method B, above, against barley powdery mildew at the 0.0002% and 0.00005%
concentrations a control of 70% and 55%, respectively, is obtained on spray application and a control of 80% and 70%, respectively, is obtained in soil drench application.
Against wheat powdery mildew in the Test Method B at the 0.0002% and 0.00005% concentrations a control of 80% and 60%, respectively, is obtained on spray applica-tion and a control 90% and 70%, respectively, in the soil drench application.
Test Method C; In vitro test employing Ustilago maydis (corn smut). Different concentrations of the active ingredient are incorporated in malt agar plates to give concentrations of 0.8 to 200 ppm a.i. (e.g. at 0.8, 3.2, 12.5, 50 and 200 ppm). The plates are then inoculated by spraying a spore suspension of U. maydis onto them or placing an agar plug containing the fungis in the centre of the plate. The plates are incubated at room temperature for 2-5 days. The efficacy of the active agent treatment is determined by comparing the growth of the fungus with that in untreated, similarly inoculated plates. The '--~ ~71866 compounds of formula I provide moderate to good cor.trol in test Method C. The compounds of Exarnple 1, 2A and 2Z-l hereinafter provide for example good control at both the lo~7er and higher concentrations in r~est Method 5 C. In an analogous test on Fusarium oxysporum f.sp. the t~ compounds of formula I, e.g. the compounds of Example 2A, 2~, 2D, 2P, 2R, 2S, 2Z, 2Z-32, 2Z-34 and 2Z-46 herein-after provide rnoderate to good control~
Fungi of the aforementioned ~enera cause considerable 0damage ln agriculture and are difficult to prevent or ~ control. In addition to combatting such fungi, the ;, compounds of the formula I are indicated to be non-phytotoxic at efective doses in ~lants subject to such fungi and are further indicated to be of particular 15intcrest as al.go actlny to combat fungi by systemic action as deterrnined, for example, in tlle combatting of Vromyces a~p diculatus on beans.
Additional tests analogous to Test Method C at 13, -; 50 and 200 ppm a.i. sho~7, except ~7here indicated, a lOO~o 20control with the compound o~ Example 1 hereinafter at at least one test dosage on the following: Phytophthora cactorum ~maximum control 45~0); Ph~tophtllo1^a c~namom (maxirnum control 65%); Aphanomyces euteiche~; Stereum pur~ eum; Thielaviopsis basicola; Pirlcularia ~zae;
___ ._____ __ _ _ _ _ 25 and Colletotrichum linde~uthianum (maximum control 90%) Additional tests analogous to Test Methods A and B
at doses of 32, 125 and 5~0 ppm a.i. conducted ~7ith the '' 1718~6 co~pound of Ex~lple 1 hereinafter show bv spray a~pIi-cation a 75%,95~and lOO~o control, respectively of Helminthosporium on barley with 20~ phytotoxicity at the higher dose.
Tes-t Method D: In vi~o, em~lovin~ Rhi~octonia solani.
The fungus is cultivated in a sterile mixture of Zonolite and corn meal (10:1 w/w) to whicn water is added in a ratio of about 1:1 (w/w); cultivation lasts for 14 days at 25C. The fungus is then mixed into a semi-sterile 10 mixture of peat and sand which then is treated with a suspension containing the formulated active ingredient to give concentration of 10 to 160 ppm (e.g. 10, 40 and 160 ppm) calculated per volume substrate. The substrate is transferred to pots of 5 c7n di~neter which are ~lanted 15 with cotton seedlings (cotyledonous stagej. The planted - pots are incllbated at 24C and 60 - 70~ relativ~ hurnidity in an incubatiorl cha~ber for 14 days, after whlch disease ; attack is determinecl by comparing the unyal attack on roots and hypocotyl with that on untreated, similarly 20 lnoculated check plants. The compound~ of formula I
provide good control in test D. The compound of ~xample 1, hereina~ter, used in the wettable powder formulation given ahote, provides for example 100% disease control with no phytotoxicity at the lower dose.
In 2 test analo~ous to ~'est l~ekhocl D run with Phoma hetae on sugar heet, the cornpouncls of formula I, e.~. khe cornpounds of forrnula 1, 1~, lE, lC, 2A, 2B, 2~, 2N, 2P, ~ ~71~66 2R, 2T, 2Y, 2Z, 2~-1, 2~-~, 2Z-7, 2Z-8, 2Z-11, 2Z-15, 2z-32, 2z-33, ~Z-3~ and 2Z-41 provide good control.

From the foxegoing it will be evident to those skilled in the art that the compounds of the present 5 invention are also indicated to be of parti.cular i~terest with regard to the control OL iln.portant soil- and seed-borne funyi, e~g. _ lmin~,ho~por _ n, Phoma, ~hizortonia and Thielavio~sis, in addition to thei.r considerable _ __ _ __ interest and value in the control of po~dery milde~s lOand rusts.
The particular value and advantages of the invention are cGnfirmed and/or further indicated in more detailed evaluat,ions of the co~pound of Example 1 herein~
after ~7hi.ch exhibi.ts the following outstanding and in sore 15cases remar~able pro~erties: 1) a persistency of action that still produces 100~ control of Ur r.~ . on pole beanr~ at spray concentrations of 0.012~ on a~p:lication 8 days before inoculation; 2) a good stability of a~ueous r~pray .suspenr.ions as ind.icated by 100So control of Uroryc,es 20app, on pole beans on application 3 days after preparation of the suspension (0.012~ concentrati.on); 3) rapid and lastlng penetration of the active substance into leaves oE
plants to be protected as indlcated by 100% control at the 0.012% concentration afteJ: a) washin~ the leaves of 25pole beans for 10 rinuteC only 10 minutes after application of the act.ive ingredient fol~o~ed by infest,a-- ~ i71866 tion with Uromyces ~EP ~ b) washing the leaves of grape-vine for 15 minutes 2 hours after app]ication of the active irgredient followed by infestatioll with Un nula, c) simulated rain washing of the leaves of coffee plant~
5 at a rain rate of SO MM/hour first applied t~o hours after application of the active inyredient for 15 minutes followed by drying, a second application of rain for 15 minutes again foLlowed by drying and then a third application of rain for 15 minutes, followed by infesta-10 tion of the coffee plant with ~emileia vastatrlx, and d)simulated rain washing of the leaves of pole ~eans at a rain rate of 50 MM/hour first applied 2 hours arter applicati.on of the active ingredient for 10 minutes ollowed by dryiny, a second application of rain for 15 10 minutes again followed by drying and then a third application of rain for lO minutes, followed by infestation of pole bean plants with Uromyces app; and 4) outstanding systemicity of action involving transport after uptake through the leaves of the upper or lower 20 portions of grapevine to the other portion whi.ch is untreated wherehy a 70% and 75~ control of UnclnuLa ln the untreated upper and lower leaves, respectively, is observed, lndicatiny that such transport lnto the untreated leaves takes place both acro- and basipetallv.
25 In still further evaluation of the compound of Example 1 herelna~ter a rungicidal activi~y of :LOG~ com-~ ~71866 pared with untreated standard is obtained on application of the active ingred.ient at a concentration of 0.012~
3 days (before sporulation) after pole beans are infested ~7ith IJromyces a~p.
When applied at a concentration of 0.05% onto pole bean plants already showing sporulation pustules of Urom~c_s ~Æ~. there is obtained a 60~ control of visible disease symptoms compared to an untreated control 10 days after application wi~h a 50% control obtained after only 10 3 days after aoplication. From the foregoing further evaluations of the compound of Example 1 the desired prope.rties of a curative activity and at least a partial eradicative e'-fect are indicated.
Other compounds of the formula I particularly the 15 compounds of Es~.arnples 2A, 2~, 2D, 2E', 2G, 2H, 2L, 2N, 2P, 2Z-1, 2Z-3, 2Z-4, 2Z-7 to 2Z-9, 2Z-11, 2Z-13 to 2Z-15, 2Z-24, 2Z-32, 2Z-33, 2Z-43 to 2Z-45 and 3 hereinafter also shcw very good to outstallding fungicidal actlvity in evaluation procedures described above. The fungicidal activity of 20 the compound of Example 2A is for example at least equal to the activity of the compound of ~s~ample 1 and also the compound of Example 2Z-33 has the same order of fungicidal activity as that of Example 1.

~ ~71866 Preferred compounds of Lhe formula I have one or more and preferably all of the following features. a) R
is alkyl of 2 to lO carbon atoms, particularly alkyl of 3 to lO carbon atoms and more particularly alkyl of 3 to

6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or cycloalkylmethyl in ,~hich the cyclcalkyl portion is of 3 to 6; b) R is hydrogen, fluoro, chloro, bromo, CF3 or Cl-C4 a].kyl; c) R' is hyd.rogen, fluoro, chioro, bromo, Cl-C4 alkyl, Cl-C~ alkoxy, all:ylthio of 1 to 4 carbon 10 atoms, CN, - yO yO
~ F -~
~herein Y and Y are as above defined; d) R"' i9 hydrogen.
The more prefQrred among the above-mentioned prererred compounds of the formula I have one or more and prefetably all of the follo~,liny features:
; 15 a) R ls alkyl of 3 to 6 carbon atoms or cycloa].kyl of 3 to 6 carbon atorns such as cyclopropyl and cyclopentyl;
b) R is hydrogen, fluoro, Cl, ~r, CF3 or Cl-C2 alkyl; and c) R' is hydrogen~ fluoro, Cl, CN, Cl-C2 aJ.kyl or Cl-C2-alkoxy; or d) R is hydrogen and R' is yO O
~ or ~~ ~

201Ocated at the para-pos~tion of Ring A, more preferably ~'~71~66 ~:
,, with Y and Y being hydrogen.
The particularly preferred compounds of the formula I are indicated to be those in which R is propyl or butyl, e.g. n-propyl, isopropyl, n-butyl, sec.-butyl, i-butyl and t-butyl, especially n-propyl, isopropyl, the branched butyls and most especially t-butyl. Other branched a].kyls of 5 to 6 carbon atoms, e.~. iscpentyl and neopentyl, are also indicated to be of parti.cular interest. Also of particular interest are those in ~hich 10 R is cyclopropyl, cyclopentyl or cyclohexyl.
The following examples further illustrate he present invention. All temperatures are in centigrade.

EX~`~PLE 1 ~-t-butyl-~lp-methyl~henvl)-l~ 2~4-triazole-l-ethan A 0.62 g portion of 61.4~ sodium hydride is washed three times with petrole~m ether and then lo ml of dimethylformamide is added ~7hile maintaining stirring. To 5 the resulting suspension is added slowly with stirring ; 1.1 g of triazole in 10 ~1 of dimethylforma~ide followed by stirring at 20 until bubbling ceases. To the resulting mixture is then added 3.0 g of 2-(t-butyl)-2-(4-methylphenyl)-oxirane followed by heating with stirring lOat 9~ for 6 hours. The resulting reaction mixture is then poured onto water, extracte~ with ethyl acetate, dried and chromatocraphed over silica gel while eluding with hexane/chloroform (50:50) to obtain a yello~7 oil which crystallizes on stand.ing to a solid which on recrystal-15lization from ethanol yields a-t~butyl-a-(p-methylphenyl)-lH-1,2,4-triazvl~-1-ethanol, m.p. 69-71. 'r~e correspond-ing h~drogen oxalate (Example lA) has a m.p. of 1~7-150, the p~neth~lbenzene sulfonate (Example 1~) a m.p. æ 21~-220 and the hvdrochloride (E ~ ?1e lC) a m.~?. of 247-250, and the scdiu~nethanolate 20 of the ~tle c ~ ound a m.p. of > 250 (Example lDI.
EX~MPLE 2 Following the procedure of Example 1 the followi.ng additional compounds of the invention are obtained:
A) a-t-butyl-a-(p-ch].orophQnyl)~lH-1,2,4-tria~ole-l-ethanol, m.p. 114-115.
2S Bj a-t-butyl-a-(o,p-~q.tchlorophenyl)-lH-1,2,4-tri-t 171866 azole-l-et~allol, m.p. 63-64.
C) a-t~butyl--(m,p-dichlorophenyl)-lH-1,2,4-tri-azole-l-ethanol, m.p. 156-157.
D) ~-t-butyl~a-phenyl-lH-],2,4-triazole-1-ethanol, 5 m.p. 84-86.
E) a-n-decyl-a-(p-methylphenyl)-lH-1,2,4-trla201e-l-ethanol.
F) a-t-butyl-a-(p-fluorophenyl)-lH-l 2,4-triazole-l-ethanol, m.p. 104-106~
10 G) a-t-butyl-a-(p-methoxyphenyl)-lEi-1,2,a-triazole-l-ethanol, m.p. 76-79.
H) a-n-butyl-a-(o,p-dichlorophenyl)-iH-1,2,4-tri-aæole-l-ethanol, m.p. 109-110.
I) ~-n-propyl-a-(p-chlorophenyl)-lH-1,2,4-triazole-l-ethanol.
~ a-l-butyl--(p-chlorophenyl)-lH-1,2,4--trlazole-l-ethanol.
K) a-methyl-a-(p-chlorophenyl)-lH-1,2,4~triazole-l-ethanol .
20 L) a-t-butyl-a-(p-biphenylyl)-lH-1,2,4-triazole-1-ethanol, m.p. 117-118.
M) a~t-butyl-a-(m,p-methylenedioxyphenyl)-lE~-1,2,4-triazole-l-ethanol.
N) a~t-butyl-a-(~-cyano~Jhenyl)-lH-1,2~4-triazole-l-ethanol, m.p. 123-124.
t 0) a-t-butyl-a-(m-nitrophenyl)-1~-1,2,4-triazole-1-ethanol .
P) ~-t-butyl-a-(p-phenoxyphenyl)-1~l-1,2,4-triazole-1-., - ~6 - 136-6878 ethanol, m.p. 112--113.
Q) a-methyl~ (m~p-dichlorophenyl)-lH-1,2,4-tri-azole-l-ethanol, m.p. 97-95.
R) -n~propyl-a-phenyl-lH-1,2,4-triazole-1-eth2nol, m.p. 81-83.
S) a-ethyl-a-(p-chlorophenyl)-lH-1,2,4-triazole-1-ethanol, Jn . p . 108-109.
T) a-n-butyl-a-phenyl-1~-1,2,4-triazole-1-etllanol, m.p. 67-68.
U) a-isopentyl-a-phenyl-lH-1,2,4-triazole-1-ethaIlol, m.p. 78-80.
V) a-n-propyl-a-(p-methylphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 86-88.
W) a-methyl-a-(p-methy].phenyl)-lH-1,2,4-triazole-1-ethanol, m p. 78-80.
X) a~n-pentyl-a-phenyl-lH-1,2,4-triazole~l-ethanol, m.p. 89-90.
Y) a-isopropyl-~-phenyl-lH-1,2,4-triazole-1-ethanol, m.p. 71-73.
Z) a-n-butyl-a-(p-chlorophenyl)-lH-].,2,~-triazole-1-ethanol, m.p. 108-109.
Z-l) a-n--butyl-a-(p-methylphenyl)-lH-1,2,4-triazole-l-ethanol, rn.p. 79-80'.
Z-2) a-methyl-a-(m-tri~luoromethylphenyl)-lH-1,2,4-trlazole-l-ethanol, a~ an oil.
Z-3) a-t-butyl-a ~mtri~luoromethylphenyl)~].II-1,2,4-triazole-l-ethanol, m.p. 120-122.

~ 171866 ~ -4) a-t-buty~-a-(m-methylphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 93-94.
Z-5) -t-butyl-a-(o-met.hylphenyl)-111-1,2,4-triazcie-l-ethanol.
Z-6) a-t-butyl-a- (p-t-butylphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 1~8-llo~.
Z-7) a-t-butyl-a-(p-ethylphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 91-g4.
Z-8~ a-t-butyl-a-(m-phenoxy~henyl)-lH~1,2,4-triazole-10 1-ethanol, m.p. 133-135.
Z-9) a-t-butyl-a-(m-methoxyphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 59-61.
Z-10) -t-butyl-a-(p-trifluoromethoxyphenyl)-lH-1,2,4-triazole-l-ethanol.
Z-ll) ~-cyclohexyl-a-(p-methylphenyl)-lH-l~2~-trlazole : l-ethanol, m.p. 102-103.
Z-12) a-hexyl-a-(p-methylphenyl)-lH-1,2,4-triazole-l-ethanol.
Z-13) -octyl-a-(p-methylphenyl)-lH-1,2,4-triazole-20 1-ethanol, m.p. 79-81.
Z-14) a-dodecyl-a-(p-methylphènyl)-lH-1,2,4-triazole-l-ethanol, m.p. 78-79.
Z-lS) a-t-butyl-a-(p-bromophenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 124-125~.
Z-16) a-neopentyl-a-(p-methylphenyl)-lH-1,2,4-triazole-l-ethanol.
Z-17) a-sec.-butyl-a-(p-methylphenyl)-].H-1,2,4-triazole---` ~1718~6 l-ethanol.
Z-1.8) a-(1,1-dimethylpropyl)-a-(p-metllyl~henyl)`-1H-1,2,4-triazole-l-ethanol.
Z-19) -t-butyl-a-(m,m-dibromophenyl)-lH-1,2,4-triazole-5 l-ethanol.
z-20) a-cyc1opropyl-a-(p-m~thylphenyl)-lH-1,2,4-triazole-l-ethanol.
Z-21) a-(2-methylcyclopropyl)-a-(p methylphenyl)-lH-1,2,4-triazole-l-ethanol.
Z-22) a-cyclohexylmethyl-a-(p.methylphenyl~ lH-1,2,4-triazole-l-ethanol, m.p~ 7~-81.
%-23)a-cyclopentylmethyl-a-(p-methylphenyl)-lH-1,2,4-tr~.azole-l-ethanol, m.p 74-76.
Z-24) a-(1-ethylpxopyl)-a-(p-methylphenyl)-lH~1,2,4-tri-l5azole-1-ethanol, m.p. 87-89.
Z-25) a-(1-meti-ylbutyl)-a-(p-methylpheny].)-lH-1,2,4-tr.i-aæole-1-ethanol.
Z-26) a-t-butyl-a-(~-bromo-p-methylphenyl)--lH-1,2,4-tri-azole-1-ethanol, m.p. 155-158.
20 Z-27) -t-butyl-a-(m-fluoro-p-methylphenyl)-lH-1,2,4-tri-azole-l-ethanol, m.p. 102-104.
z-28) -t-butyl-a-(m-chloro-p-methylphenyl)-l~i-1,2,4-triazole-l-ethanol, m.p. 144-147.
Z-29) a-t-butyl-a-(m-chloro-m-J,~ethoxypilenyl)-lI-i-1,2,4-25 triazole-l-ethanol.
Z-30) a--t-butyl-a-(p-tri.fluoromethyl-m-~hlorophenyl)-lH-1,2,4-triazole-1-ethanol.

- t 171~6~

Z-31) a-t-butyi-a-(m-chloro-m-phenoxyphenyl)-lH-1,2,4-triazole-l-ethanol.
z-32) a-cyclopentyl-a-phenyl-lH-1,2,4-triazole-1-ethanol, as an oil.
z-33) a-cyclopropyl-a-(p-chlorophenyl)-lH-1,2,4-tri-azole-l-ethanol, as an oil.
Z-34) a-cyclobutyl-a-(p-~luorophenvl)-lH-1,2,4-triazole-l-ethanol, m.p. 83-84.
Z-35) -t-butyl-a-(m,p-dimethylphenyl)-lH-1,2,4-triazole-10 l-ethanol, m.p. 120-122.
Z-36) a-t-butyl-.(o-methoxy-m-methylphenyl)-lH-1,2,4-tr.iazole-l-etnanol.
z-37) a-t-butyl-a-(o-methyl-p-methylthiophenylj-lH-1,2,4-triazole-l~ethanol.
15 Z-38) a-t-butyl--(m-methyl-p.phenoxyphenyl)-lH-1,2,4-triazole-l-ethanol.
; Z-39)- a-t-butyl-a-(o-methyl-m-nitrophenyl)-lH 1,2,4-i triazole-l-ethanol.
Z-~O)a-cyclobutyl-a-phenyl-lH-1,2,4-triazole-1-ethanol, 20 a~ an oil.
Z-41) a-sec.-butyl-a-(p-chlorophenyl)-lH-1,2,4-triazole-1-ethanol, as an oil.
Z-42) a-t-butyl-a-(m,m-dichlorophenyl)-lH-1,2,4-tri-azole-l-ethanol, m.p. 145-147 Z-43) -t-butyl-a-(m-chlorophenyl)-1~l-1,2,4-triazole-l-ethanol, m.p. 126-127 Z-44) a-t-butyl-a-(p-cyanophenyl)-lH-1,2,4-triazole-~; .
., ' 171~66 l-ethanol, m.p. 105-107.
Z-95) a-cyclopentyl-a-~p-methylphenyl)-lH 1,2,4-tri-azole-l-ethanol.
Z-46) ~-isobutyl-a-phenyl-lH-1,2,4-tria701e-l-ethanol.
5 z-47) a_(l-methylcyclopropyl)-a-p.methylphenyl-lH-1,2,4-triazole-l-ethanol, m.p. 126-128.
Z-48) ~-methyl-~-(p-biphenylyl)-lH-1,2,4-triazole-1-ethanol, m.p. 115-120.
Z-49) ~tert.butyl-~-(p-iodophenyl)-lH-1,2,4-triazole-1-10 ethanol, m.p. 78-80.
Z-50) ~-(3-heptyl)-~-(p-methylphenyl)-lH-1,2,4-triazole-1-ethanol, oil.
Z-51) ~-(2-pentyl)-~-(p-methylphenyl)-lH-1,2,4-triazole-1-ethanol, m.p. 89-91.
Z-52) ~-(tert.butyl)-~-(mlml-dimethylphenyl)-lH-l~2~4 triazole-l-ethanol, m.p. 128-130.
Z-53) a-tert.butyl-~-(3-nitro-4-methylphenyl)-lH-1,2,4-triazole-l-ethanol, m.p. 160-161C.
Z-54) ~-tert.butyl-~-(3,5-dinitro-4-methylphenyl)-lH-1,2, 204-triazole-1-ethanol, m.p. 194-196C.

,, , . .. ,,, . , . .. . . , . , . . , - ~ ~ , , ~ l 7186~

- 30a -a-t-butyl-~-(p-carboxyphenyl) -lH-l, 2, 4-triazole-l-ethanol, and potassium salt A mixture of 1.3 g of a-t-butyl-a-(p-methylphenyl)-lH-1,2,4-triazole-l-ethanol, 1-89 g of potassium permang-nate and l9 ml of water are refluxed with stirring for l hour. The resulting reaction mixture is filtered while still hot, the residue washed with 10 ml of hot water, the filtrate treated with charcoal and concentrated in vacuum to a small volume (4 ml) which is dried under high vacuum to obtain the potassium salt of a-t-butyl-a-(p-carboxyphenyl)-lH-1,2,4-triazole-1-ethanol, m.p. 194 , (decomposition).
; The above reaction is repeated using three times the amounts of the materials specified above except that the filtrate i8 washed with ether, the ether washing washed with water, the combined aqueous layers acidified with concentrated hydrochloric acid with stirring until no additional precipitate formed, and the precipitate ~0 collected by filtration, washed several times with ether and dried under a high vacuum to obtain ~-t-butyl-a-(p-'~

! l 718~6 - 31 - 1~6-6~78 carbo~yphenyl) -lH-l, 2 4-triazole-1-ethanol m.p. 248-250.
EX~iPLE 4 2-(t-butyl)-2-(4-methylphenyl?-oxirane A 2.2 g portion of 61.4% sodium hydride is washed 5 three times with petroleum ether then 70 ml of dimethyl-sulfoxide added and the mixture heated with stirring to 70 and carried to 85 by the exotherm after ~Jhich the mixture is heated at 75 for 40 minutes. The resulting mixture is cooled to 0 in an ice/salt bath and then under lOa nitrogen blanket there is added dropwise a solution of

7.0 g of trimethylsulfonium iodide in 50 m]. of dimethyl-sulfoxide and 20 ml. tetrahydrofuran while maintaining the temperature belo" 18. To the resulting mixture is then added with stirring under the nitrogen blanket a solution of 3.0 y of t-butyl-p-methylphenyl ketone in 30 ml of tetrahydrofuran whi].e maintaining the temperature below 10. The resulting mixture is stirred at 0 for 30 minutes and then at room temperature for 2 hours. The resulting reaction mixture is then poured onto 400 ml 200f water, extracted with me~hylene chloride, the organic phase ~ashed with water and then brine, dried and evaporated to obtain a yellow oil of 2-(t-hutyl)-~-(4-methylphenyl)-oxirane.

7ia66 ~ 31a -~-(tert.-butyl)-~-~p-methoxycarbonyl-phenyl)-lH-1,2,4-triazole-l-ethanol To a flask containing at 0 an ether solution of CH2N2 prepared in the conventional manner from 3.39 9 of N-methyl-N-nitroso-p-toluenesulphonamide is added dropwise, while maintaining ice bath cooling, a solution of 1.5 g of -(tert.-butyl)- -(p-carboxyphenyl)-lH-1,2,4-triazole-l-ethanol in 85 ml of dry tetrahydrofuran. The resulting mixture is allowed to stand under ice cooling until thin layer chromatography analysis shows an essen-tial absence of the triazole starting material. A few drops of acetic acid are added to destroy excess diazo-methane, the mixture is then concentrated to remove tetrahydrofuran, the concentrate extracted with ether and washed with 2N NaOH solution. After drying white crystals are formed on standing. The crystals are recovered by filtering and recrystallized from CH2C12/ether to obtain the title compound, m.p. 152-154.

Claims (17)

Claims:

1. A compound of the formula wherein R° is t-butyl, cycloalkyl of 3 to 8 carbon atoms or cycloalkylalkyl of 4 to 11 carbon atoms in which the cycloalkyl portion is of 3 to 8 carbon atoms and the alkyl portion of 1 to 3 carbon atoms, said cycloalkyl and cycloalkylalkyl groups being optionally substituted by one or two alkyl groups of 1 to 3 carbon atoms, R is hydrogen, halogen having an atomic number of from 9 to 35, alkyl of 1 to 4 carbon atoms, mono-, di- or tri-haloalkyl of 1 to 4 carbon atoms in which the halo is independently an halogen having an atomic number of from 9 to 35 , alkoxy of 1 to 4 carbon atoms, alkylthio of 1 to 4 carbon atoms, or nitro, and R' is hydrogen, halogen having an atomic number of from 9 to 53, alkyl of 1 to 4 carbon atoms, mono-, di- or tri-haloalkyl of 1 to 4 carbon atoms in which the halo is independently an halogen having an atomic numbex of from 9 to 35, alkoxy of 1 to 4 carbon atoms, mono-, di- or tri-haloalkoxy of 1 to 4 carbon atoms in which the halo is independently an halogen having an atomic number of from 9 to 35, alkylthio of 1 to 4 carbon atoms, nitro, -CN, -COOR", R" is hydrogen, alkyl of 1 to 4 carbon atoms, R'" is hydrogen, an halogen having an atomic number of from 9 to 17 or alkyl of 1 or 2 carbon atoms, Z is oxygen or sulfur, or R and R' together represent alkylenedioxy of 1 or 2 carbon atoms substituted onto adjacent carbon atoms of the phenyl Ring A, and Y° and Y are independently hydrogen, halogen having an atomic number of from 9 to 35, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, in free form or in agriculturally acceptable salt or metal complex form.

2. A compound of Claim 1 in which R° is cycloalkyl of 3 to 8 carbon atoms or cycloalkylalkyl of 4 to 11 carbon atoms in which the cycloalkyl portion is of 3 to 8 carbon atoms and the alkyl portion of 1 to 3 carbon atoms, said cycloalkyl and cycloalkylalkyl groups being optionally substituted by one or two alkyl groups of 1 to 3 carbon atoms.

3. A compound of Claim 2 in which R is hydrogen, halogen having an atomic number of from 9 to 35, CF3 or C1-4 alkyl, R' is hydrogen, halogen having an atomic number of from 9 to 35, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylthio, CN, or in which Y° and Y are as defined in Claim 1, and R"' is hydrogen.

4. A compound of formula I, in which R° is t-butyl, R is hydrogen, R' is 4-CF3O and R"' is hydrogen, a halogen having an atomic number of from 9 to 17 or alkyl of 1 or 2 carbon atoms.

5. A compound of formula I, in which R° is C3-6 cycloalkyl or (C3-6 cycloalkyl)-methyl, R is H, F, C1, Br or C1-2 alkyl, R' is F, C1, Br, C1-2 alkyl or C1-2 alkoxy and R"' is hydrogen.

6. The novel compound .alpha.-cyclobutyl-.alpha.-(p-fluorophenyl)-1H-1,2,4-triazole-1-ethanol.

7. The novel compound .alpha.-(l-ethylpropyl)-.alpha.-(p-methyl-phenyl)-1H-1,2,4-triazole-1-ethanol.

8. A compound of Claim 5, wherein R° is cyclopropyl.

9. The novel compound .alpha.-cyclopropyl-.alpha.-(p-chlorophenyl)-1H-1,2,4,-triazole-1-ethanol.

10. A compound of formula I

in which R° is t-butyl, R is H, F, C1, Br or C1-2 alkyl, R' is F, Cl, Br, C1-2 alkyl or C1-2 alkoxy and R"' is hydrogen.

11. The novel compound .alpha.-t-butyl-.alpha.-(p-methylphenyl)-1H-1,2,4-triazole-1-ethanol.

12. The novel compound .alpha.-t-butyl-.alpha.-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol.

13. The novel compound .alpha.-t-butyl-.alpha.-(p-methoxyphenyl)-1H-1,2,4-triazole-1-ethanol.

14. The method of combatting phytopathogenic fungus in plants, seeds or soil comprising treating said plants, seeds or soil with a non-phytotoxic fungicidally effective amount of a compound of Claim 1.

15. The method of Claim 14 in which the compound is a) .alpha.-t-butyl-.alpha.-(p-CF3O-phenyl)-1H-1,2,4-triazole-1-ethanol or b) .alpha.-cyclobutyl-.alpha.-(p-fluorophenyl)-1H-1,2,4-triazole-1-ethanol or c) .alpha.-(l-ethylpropyl)-.alpha.-(p-methylphenyl)-1H-1,2,4-triazole-l-ethanol or d) .alpha.-cyclobutyl-.alpha.-(p-chlorophenyl)-1H-1,2,4-triazole-l-ethanol or e) .alpha.-t-butyl-.alpha.-(p-methylphenyl)-1H-1,2,4-triazole-l-ethanol or f) .alpha.-t-butyl-.alpha.-(p-methoxyphenyl)-1H-1,2,4-triazole-l-ethanol.

16. The method of Claim 14 in which the compound is .alpha.-t-butyl-.alpha.-(p-chlorophenyl)-1H-1,2,4-triazole-1-ethanol.

17. A process for the production of compounds of formula I, stated in Claim 1, 2 or 3, which comprises a) reacting a compound of the formula II

II

wherein R°, R, R' and R"' are as above defined, with a compound of formula III

III
wherein X is an alkali metal in an inert organic solvent, b) obtaining a compound of formula Ia Ia wherein R° and R are as defined above, by oxidation of the CH, group of a compound of formula Ib, Ib wherein R° and R are as defined above, or c) obtaining a compound of formula Ic, Ic wherein R and R° are as defined above and Alk is C1-4alkyl, by esterification of a compound of formula Ia with an alcohol of formula IV
Alk-OH IV
wherein Alk is as defined above.