Carbamoyl-triazolyl-0,n-acetals, their preparation and use as fungicides

The present invention relates to a process for the preparation of carbamoyl-triazolyl-O.NHaoetiaIs of the form I:

O-CO-NHR / o -O-CH-CH-C (CH₃bx / -^Z In which R represents ό alkyl, halogenalkyl, allyl (eoxisaaTboni.l, afooxiallichill, phenylsubstituted phenyl) alkylsulphonyl.all'C'henM-iciarbaimoyl, X denotes a halogen atom, an alkyl group, cycloheoxyalkyl] , halogemailkyl, alkylphio, alkyloxyicarbyl, optionally substituted phenyl or phenoxy, optionally substituted phenylalkyl, an amimo, cyano or nitro group and n represents whole numbers. between 0 and 5, as well as the addition salts with their acids and their complexes, metal salts.

They are known proided.ee for the preparation of some · ΐιΦ9ΕθιΙΐ1-Ο, Ν-θ'θ0ΐ »ί1ΐ hereylated by the coru es derivative tiru'baîr, punzaitoirL of trlazol.il with dte, acclaimed, or acid halides, compounds having proprietary patents (fungus patented) , RFG, no. 2600799),

The present invention extends the range of fungicides reallifzinid fungicides with form5 to I above egg yolk. Higher thetate, in that they are derived from triazoles ha ving the general formula. II:

_ ^OH / A> -O-CH-CH-qcH₃)₃7 „ | /^N\

N ^{Q! | T} in which X and n have indi20 signi fi cance of sheep before, they react with isocyanates of general formula III:

: .. O == C = NR (IU) in which R has sificaifiioaATIille indficaltie 25 before, the components being iuiaffie in equimolar proportions '' and the reaction takes place in itetrabidrofuran in the presence of triethylamine and laureate of dibutylthanium,

3o the reflux temperature.

. ...... THE PRICE OF LAW. 22.43

17 embodiments are given below, in accordance with the present invention.

Example 1

Ό CO-NH CH₂-O GH₃R o R - ζ O \ - O-CH —'CH - C (CHj)₃ /^N\

II N N_ ||

505 µg (1.5 mol) 1- (4-biphenyloxy) 3,3-dimethyl-1 (1,2,4-trazazole-14) are heated.

-iyl) -b.utan-2-ol (form A ') and 140 g (1. 6 mole) of methoxyimethyl isothiocyanate in 2.5 1 tetrahydrofuran in the presence of 40 ml> trietUamine and 1 ml larurnatt of dibutyl-sla5 mu for 48 h with no flow. After this, the solvent is vacuumed and the residue is vacuumed! s, e treats with 3 1 petroleum ether. The precipitate crifetaOan formed is mixed with 1.5 liters of ether dlizcxprogillc. it^t0 obtain 528 g (82.5% of theory) of 1- (d -phenylylloxy) -3,3-sdimeithiyl-2-methoxymethylloarbamyloxy-1- (1,2,4-triazole-ii), -button (form A *) with melting point 85 ...

98 ° C.

In the analogous manner, the compounds of the examples shown in Table 1 are prepared.

Table 1 1

O-CO-NHR / o ^ -O-CH ^ H-CiCHab X- / i /^N\

II N

N__J |

<td>Example no.</td><td>- x "</td><td>R</td><td>- Drilling point, ° C.</td>

<td> 1</td><td> 2</td><td> 3</td><td> 4</td>

<td> 2</td><td></td><td>- (CH_?),-BUT</td><td>138 ... 141 vfofoima iB *).</td>

<td> 3 · '</td><td>^ &lt;S&gt;</td><td>-COaOCHj</td><td>184 ... 185 (form B)</td>

<td> .4</td><td></td><td>-CO-OC₂H₃</td><td>164 ... 166 (form-B)</td>

<td> 5</td><td>/ - &lt;I&gt;</td><td>But</td><td>103 ... 105 (form A)</td>

<td> 6</td><td></td><td>-CO-OCH.</td><td>120 (form A)</td>

<td> 7</td><td>4- &lt;O&gt;</td><td>-CO-OC, H_S</td><td>100 (form A)</td>

<td> 8 :</td><td> «-&lt;£&gt;</td><td>;, -CIVO-CH</td><td>141 .., 144 (S-shape)</td>

<td> 9</td><td>4- &lt;O&gt;</td><td>-CO-N-SO_ofCH_{, and}and CKrCH-CHD</td><td>141,. 144, (form B)</td>

<td> 10</td><td></td><td>- (CiHtîJî-CHjCHjJ-CH</td><td>109 ... Π5, (formal in)</td>

<td></td><td></td><td>C '(CH._:)_S</td><td>¹ · ^r</td>

<td>11 rf; ·</td><td>⁴ &lt; &gt;</td><td> _/’()\ \_/ ^X Chi-CH-COOCH,</td><td> 194...200</td>

7573¹)

<td> 1 ·</td><td> 2 '</td><td> 3</td><td> 4</td>

<td></td><td></td><td>gh₃\</td><td></td>

<td> 12</td><td>4- &lt;o&gt;</td><td>-ΛΆ \ ° /</td><td> 158...165</td>

<td></td><td></td><td>I-CsHZ</td><td></td>

<td> 13</td><td>"-θ</td><td>- &lt;o&gt; C (CH₃)₃</td><td> 193...206</td>

<td> 14</td><td>4- &lt;ό&gt;</td><td>- • (a) -op</td><td> 148...155</td>

<td></td><td></td><td>^XOCH₃</td><td></td>

<td> 15</td><td>ihCI</td><td>-CO-OCH</td><td>151 ... 154 (-A form)</td>

<td> 16</td><td>4- &lt;ό&gt;</td><td>-CH, OC₂H₅</td><td>140 (x HCI)</td>

<td> 17</td><td>¹ (A</td><td>- (CH₂)._r-O-CH₃</td><td>100. (x HCI)</td>

*) Form A and Β - defines one of two possible geometric isomers.

It is easy to see that the egg derivatives I have two thousand carbon asymmetrical grandparents; they can thus be in the form of erythro- or freo-. in both aazes. they are in the form of prinlcaiplaR '. by paoemate. - As it was clear from the examples, the compounds of thearbaimoillifcriaBolâd -O, N-acetyl as general formula I are prepared by the reaction of the triazolyl derivatives of general formula II:

OH z- \ ICO&gt; -O-CH-CH-C (CHJ₃ x / ~^z | /^N\

II NN II 'in. 'which X and n have'. before and -isocyanates of general formula III:

- O — C = NR '·' (III) ²⁵ in which'R has the meanings indicated above, in the presence of a student^: ventual in the presence of a caibalizer. _3θ Further, the carbamoyl-triaz'dyl-OjN-ac ethals of formula, 1_; obtained ,. according to the invention, they can be transformed into their salts with acids !, '/ respect can be. bro, bro. through the fascination with '/ metal strings in 35 ζdbreap-lightening metal complexes,',_: .But though _fliţiÎlizează,_;ica ,, ampi% prime, lA (4-biÎfen ^ iibxi) ₉ -3 / 3-.dÎjpefibld '(4,2,4 / -friiaEo, blril) -bu &amp;^:n_rQ2-'0i_;-.and_and._andMethioethyl methyl acetate, the reaction progress may. the following reaction scheme has been reproduced:

OH \ ° / “\ /^N\

II N

Ν I!

GCH₃-O-C'H-₂-N-C-O ^:--^--“---“

O-CO-NH-CHj-O-CHj / rA-ZiA

-O-CH-CH-qCHsh /^N\

II NN || . The derivatives of photosylated triazazoyl or a raw material are generally defined. formula II. In the same formula, X preferably represents halogen, amber, cyan, nitro, straight chain or branched alkyl and up to 4 atoms; of icăor • bon, cfeloatehiil ou, 5 da 7 atoms of parbgn, in particular cyclohexifi, haiogemailchiil cp, up to ,, ion 2 aftQipi of carbon and up to

... 5 ha atoms, logen, in spediial atoms of - efflmor and chlorine,, of example, thousands of peas, zhnthe preference of the alkoxyicarbonyl in all with up to 5 carbon atoms, of the '' febicUşi ailichiltio 'de' 'each egg chops up to 2 carbon fatons.' ΐή · other than your own, X is still 'preferably. substituted phenyl and .phenoxy groups, as sub75 / 3ί&gt;

preferred being: h-halogen atoms, atmiue, -c-ian, n-iltro or a «l .. chil. «With 1 ... 2 carbon atoms, then 'also preferably phenylalkyl groups with 1 ... 2 carbon atoms then also preferably phenylal chyl groups with 1 ... 2 atoms of« carbon in the alkyl test, possibly suibsltiitiirilt-e, the substituents on the alkyl moiety being preferably groups of "alohyloarbonyl-oxy-total with up to 3 carbon atoms and the substituents on phenyl preferably halogen, nitro and cyan. The index n preferably represents the numbers from 0 to 3.

The starting materials of formula II are known (Patent, RFG, no. 2324010). Isocyanates usable as raw materials in the desert process - are generally defined by formula III, ίη - in this formula, R preferably represents a group, alkyl or linear or branched coffee with 5 to 4 to 12 «oainbon, hafogenaijdhse to 4 carbon atoms and up to 5 identical or different halogen atoms, - especially fluorine and ethyl atoms, also atoxo-iububonium and altoxlialebiyl groups each day egg 1 ... 4 carbon atoms take the remaining alkyl. R is also preferably a phenill-substituted grapevine with one or more substituents, which may be less¹ preferably: atlchil or linear or branched moiety with 1 ...- 4-carbon atoms, alkoxy and alkylthio each time with 1 ... 2 atoms of carbon, halo-halogene or o-up to 2 atoms of "shaft and up" to 5. identical or different ha-logene atoms, in particular 'phryl and chlorine atoms, as well as 1-alkoxy-alkylthioalbbonylshenyl;¹ of carbon lia restuil aliehil and 2., - 4 laltomd of carbon in the -alichenyl side. R mal may preferably represent an alkylsulfond-aliohenyl-oarbamolill group with 1, 4 carbon atoms at the alkyl residue and 2 ... 4 carbon atoms at the a'-lioheuill residue.

Isoociiaimations of the general formula III are known and can be prepared by the generally known ic-on methods, known for example by the reaction between 'himSnje and' (fosgen-'ișî '&lt;iiio &amp; il5Mreia fe oontihuare. ¹ 'during the feasts you can use advance. 'IaijdS as debibivabates - you do the students of the organiiiiiiiiiiii organiii: Among the abbeys, they are preferably found' «etonelh, for example^;dfe '^ - dfcefon *,' dar'in * -.^;«AicjeftioTi (a- and me '' 'tiletylphetone, hitMlIi, oa · for example, pipprîgmihfV' and. Fo special '' aoetonStrîl. · _Λ / eterM,&gt; joa-. itfririahitdroforanι. · and . piioxan; -sflssteȚÎfc eaaiăpeithitiuî Λ .. '. © ΐϋ1; ί jfaiîidrocaîbu “Lîâle-i ianoimăitîioes, ·' - - | âa't5be # fflen -« β® 'itolluen' '-Șî hțdroloi ^ bhfîile' · icatfim

methylene chloride, carbon tetrachloride or -olaroforimujl.

«In catalytic catalysts, preferential lipids may be used,« oxytriethylamine and pyridine, or organic compounds of stianiiulluî, a feiucaf of ditoultilsiBamiiin.

Reaction temperatures may vary, depending on the range. In general, it works at- (temperatures between Ό and 100 ° C, preferably between 20 and 70 ° C.

In carrying out the process according to the invention, it is preferably worked in equimolar proportions. For the isolation of the compounds of formula I the solvent is distilled and the residue is processed by the usual meffodle.

During the preparation of the addition salts of the compounds of formula I with acids, all acids that are physiologically tolerated can be forgotten. These include haylogenetic acids, for example ephorhildric acid and bromofluoric acid, in particular hydrochloric acid, followed by phosphoric acid, nitric acid, sulfuric acid, oarboxylic acids and hydroxy monohydroxy acids. bi-functional ', an o-example «alephoiic, mal-eic acid, -suric acid, fumarir atild, tartaric arid, (citric acid, salicylic acid, sorbic acid, lactic acid, as well as sulphonated acids, as for example, «Jp-lboteenisuilfonllc acid and 1,5-n acid.

- The salts of the compounds with the formula can be prepared in a simple way, by conventional methods of preparation «of charcoal, for example, by dissolving the butter« compound of formula I suitable inert solvent and «adding acid, for example .aciid chlorhildrla gas; They can be isolated in the known manner, for example by means of .fiilttiaire. they can possibly be purified by washing with an inert organic solvent.

For the preparation of chelmpleicles with metal salts «of« compounds in formula I the «Ufoa look in. moid - advantageous salts of the metals from the main groups II to IV and from the secondary groups I and II as well as IV and VIII VIII, reading for example copper, zinc, miamg-ano, magmezini, «citani, iron and nickel. «As anions you have¹ those saline salts «usable for them come from fiziollpgiio compatible killers. Among these, he cites «hiatogehihydriic acids, .exetaipHu hydrochloric acid and hydrochloric acid, then phosphoric, nitric and sulfuric acids.

'Compiecșiișcu with metallic salts and compounds, I formula I is simply prepared according to conventional methods, for example ήρπη diitolVaifea'. «Rmetalfee salt in a. 'alcohol,' for example, 'in ethanol, and addition¹ be the compound with the furnace I.

The metal compounds can be isolated in the known way, for example by filtration, and possibly purified by recrystallization.

As examples of compounds - especially of the additives according to the present invention, the ones from the examples in the following table are mentioned; Î- {4-dorphene • xi) -3,3-dimethyl-'2-ine toxime til - blind aimooyloxl-ί- (1,4,4-triazol-1-yl) -b.ut'an; 1- (2,4-dichlorophenoxy) -3,3-dian. Tll-2-methexymethylearbamoyloxy-1- (1,2,4-thiazol-1-yl) -butane; 1- (4-carboxyloxy) -3,3-dimethyl-2-trifluoromethylcarbamoyloxy-1- (1,2,4-triazol-1-yl) -butane; 1- (4-dithiylenyloxy) -3,3-dimethyl-2-IrifluoromethylciaTibamoyloxy -1- (1,2,4-tri-azol-1-yl) -butyl.

It was not surprisingly found that C'arbamoiQdriazolil-ON-acet'alii, according to the invention, has a considerably improved fungicidal activity in relation to the compounds having • the chemical structure and the most .appropriate activity, as they are • Ιηβζ-οΰΙ , -Ν-βίοβΙάΙ-Μ -acylates and in. Specials 2 - atlichiyl-carbonyl oxy- 3.5 - dianeiifcl -1 -fe noxi-1 - (1,2,4-triazol-1-yl) -phenyl substituted hutaases . They also feel more active than ethylene-1,2-bis-di'tiiaoair-zamidatr.il of zinc, an iconic material that has the same activity direction.

In the concentrations necessary for the control of fungi, the active substances according to the invention do not have a harmful action. ns-upra of cultivated plants. For this reason they are suitable for the use of a plant protection agent in the fight against fungi, the fungitoxic compositions are introduced in the protection of plants for the control of the plant species: Plasmodiophoromycetes, Oomycetea, Chytridiomycetes.es, Zytridiomycetes.es , Basidiomycetes, Deuteromycetes.

.-Active substances, oonif-oxm, present invention, year one. .spirit lairg of this year and can be jufified against parasitic fungi © ane attacks .the above part of the soil ialplants and ether attacks the plants from. soil, as well as the impotable - seed-borne pathogens. The compounds, according to the invention .exercise .o .a particularly good stewardship of parasitic pimples of the parts^rof plants above the husband.

The compounds, according to the invention, are commonly used with particular results as .hune agents. of protection of leaflets in combating varieties of Venturia, for example against. 'the agent-brown stain of the apple fiBasidadium dendriticum),: by jLfr0iîiyeeî., &lt;âa derexemplu' dmpotayia. ageiduluii-'de,) dew a.-fasoJei ('4 / roinyees p / iascolij), -, as well as in the rcomJbat'erea of ​​the varieties sriey, xBivyt0phthora and_:.a of diseases of oerealc. ·; -; J. C's. r.

io

Acit-ivil compounds, according to. The invention can be used to treat seeds that are uranase &lt;to be sown. .and of the «ol, as well as for the treatment of the parts of the plant by the dieaisuipna of the soil.

The active substances can be formulated in the usual way as -solutions, emulsions, powders, -suspensions, -powders, foams, pastes, powders, granules, aerosols., © onieentnaibe suispendabi-them ^ emuJsIB powders for seeds, natural or synthetic materials - impregnate I © - with the active substance, in the presence of it. - fine in polymeric materials and in seed dressings, then they can be presented in formulations with ignition batches, - as they are - cartridges, dosages, supply spirals and the like, as well as - cold fog formulations they were warmed up by the ultra-low volume (ULV) procedure.

These are formulations. it is made in the known way, for example, by mixing the active substances with dilution materials, where we feel liquid substances, pressurized gases and / or maienial © of solid support, possibly with the use, by the air, of the active agents humor. surface, -oa emullgafori and 7 »have -dispersants and / or foaming agents. In oasis-1 when. the water is used as a dillnamt, it can be used again, and it can be used as an organic substance or as a soft drink. As liquid solvates' e can Jiuia into consideration in essence: ichthenocarbons aromatic hydrocarbons, aromatic hydrocarbons, such as xylenes, foliars, or alChiUnjaftaline, be chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethane, methane, chlorine, paraffin, paraffin, for example, paraffin, for example, 'petroleum,' alicooyl, 'oa-' butanol or glliiool and also 'ethers and esters thereof, ketones aioeitone, methylthiethetetone, methylisobutillcotone or -clohexanoin, are strongly polar, © a dimethylformamide and 'dlimetiUsulfoxiduil, as well as water; by dilution or support material 'gaseous liquefaction' means alleles. liquids which at 'normal temperature and normal pressure are gaseous, for example. aerosol spraying gases, such as' halogenated hhhuoarburâlle and, by Aseania; the button, pr, opane, nitrogen, and bioxiildil of icanbon; "solid support materials" means "natural stone flour, such as caoil.N'n'ile, iamgilia, talic, chalk, quartz, attapulgita, .montmorîllonita. and the diatomifcele, the synibtic piatra of 'synibtic',. cajs'ilioe film. dispersed aluminum oxide, iSifi-ions; by materials of, support penitr, u '.- .. granule'. understand the natural stone

Crushed and fractionated such as calcite, marble, pumice,. Sepioiliite, dofomite, as well as organic and organic diphenic synthetic grains and granules of organic materials, such as wood sawdust, coconut shells, corn and teal cocoons. I, tobacco pines; By emiaisioinary and / or foaming agents are meant nonionic emulsions or antonias, such as polyethoxylated fatty acid doors, polyethoxylated fatty atoms, for example alkylylpongoyloyl esters, alkyl aryl, sulfyl aryl, sulfyl aryl, sulfyl aryl; as well as nudroPizaite of light; dispersants, for example, lignin-sulfite lithium and mytilioetalose.

In this formulations, adhesive agents can be used, such as cardoxylmetricalJiceiuiosis, podibers suib in the form of puioerl, granules or latex, its natural synthetic, such as, gum arabic, alcohol podi vin and ic, pliaoeitait vini.

Colored majors, such as inorganic pigments, for example iron oxides, titanium, ferocious and organic dyes, for example ahzairmar dyes, azomothalphthalocyanide stains, and fertilizers from, have been used. milcroelemanite, a salt of iron, manganese, boron, copper, comolibden and zinc.

the formulations generally contain between 0.1 and 95% by weight of the aotite weight, preferably between '' 0.5 and 90%.

Active 'stubstants' according to the invention can be found in these formulations in combination with some known active substances, such as fungicides, insecticides, acaricides, nematocides, herbicides, protective agents against the attack of birds, substances to accelerate growth. fertilizers and soil structure improvement agents. "

Laotonic substances can be used, in the form of mixtures formulated or in the form of lufiiflification. Obtained. To dilute them further, for example, ready-to-use solutions, emulsions, suspensions,^; powders, pastes or granules. The application is done in the usual way, for example, by updating the splash, '. Pulveriiz.aire, ,,_: dust, 'scattered the air, whistling. dry, .washing liquid, 'dripping with' his suspension Inlay. ; // A,, /. 77 in the .forms of⁷ application, '/ .concentrated by .aidUrve substances may be' varied, in one. wider range ~ at 'use', ^ ''. fungicide for haze. ' ΈΙ, θ, / ρόί .ΐί /. various .. between; o, l and) D, 00b01_and% 'AA7₁greittâţe, 'iiar_it it is preferably between 0.05 and 0.0001%. vpi ^ utrdtaibia of the seeds is used^:bgenerally · 'quantities of' active substance between &lt;0.001 and .: 50 g per kilogram of seed, preferably 0.01 to g per kilogram of seed.

For the treatment of the soil, quantities of active substance between 1 and 1,000 g per m are required³ of soil, especially 10 to 200 g / m³.

The various possibilities of use are solved by the following tests:

Test A. Test with Pusicladium (apple) / protection:

- solvent: 4.7 parts by weight added;

- emulsifier: 0.3 parts by weight of alkyl alcoholic glycolic ether, · - water: 95.0 weight percent.

The amount of active substance required to obtain the desired concentration of active substance in the spray liquid, mix with the indicated amount of solvent and dilute the concentrate with the indicated amount of water, which contains said addition.

Apple seedlings that are in the stage with 4 .., 6 leaves are sprayed with the spray liquid, until the drops drop by watering. The plants remain in the greenhouse for 24 hours at 20 ° C and a relative air humidity of 70%. Further, they are inoculated with an aqueous suspension of conidia of the brown - apple stain agent (Pusicladium dendriticum) and incubated for 18 h in a humid room at 8 ... 20 ° C and relative humidity of the air. 100%. .

After that the plants are kept again for 14 days in the greenhouse. 15 days after inoculation, the attack on the seedlings is determined. The evaluation values ​​obtained are recalculated in percentage attack. 0% represents the lack of attack, 100% means that the plants are complete-attacked.

In this test the compounds described in Examples 1, 2, -8, 16 and 17, according to the invention, show a very good activity, which is &lt;net superior _;that presented by the compounds known in the art.

Test B. Uromyces test (iasole) / protection;

-, solvent: 4.7 parts by weight. Acetone;

- emulsifier: 0,3 parts by weight .eter. .alchilarilp.oliglicoii; . .

n water: Ό5.0 parts by weight.

'Amount of active substance required' to obtain the concentration of · substance: active in the spray liquid, mix with the amount of 75739 declared by the solvent and dilute the concentrate with the indicated amount of water, which contains said addition,

Young bean plants, which are in the stage with two leaves, sprinkle with the sprayed liquid until the drops drop by watering. The plants are kept for drying 24 h at 2O ... 22 ° C and 70% relative humidity in the greenhouse, then they are inoculated with an aqueous suspension of uredospores of the bean rust agent (Uromyces phasoli) and incubated for a while. 24 h in a humid room, dark at 2O ... 22 ° C and relative humidity of 100% air.

The plants are kept, afterwards in the greenhouse under intense lighting, for 9 days at 20 ... 22 ° C and a relative air humidity of 70, 80%.

The attack on the plants is determined 10 days after inoculation. The evaluation values ​​obtained are recalculated in percentage attack. 0% represents the lack of attack, 100% means that the plants are slightly overgrown.

In this embodiment, the compounds resulting in the preparation examples 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, .13, 14, 15, 16, 17, according to the present invention, present a very good activity, which is clearly superior to that presented by the well-known compounds of the art.

Test C. Phytophthora test (tomatoes) / projection:

- solvent: 4.7 parts by weight acetone;

- emulsifier: 0.3 parts by weight alohilaril-potiglycolic ether;

- water: 95.0 parts by weight.

The amount of active substance required to obtain the desired concentration of active substance in the spray liquid is mixed with the indicated amount of solvent and the concentrate diluted with the indicated amount of water, which contains said addition.

'Young tomato leaflets with 2 ... 4 leaves are sprayed with the spray liquid until the drops drop by watering, the plants are kept 24 h at 20 ° C and the relative humidity of the air 70% in the greenhouse. They still feel inoculated, with a suspension-aided by spoilers of Phy-.fophihprainf.es, taris. .The plant is. bring to a humid room with 100% air humidity and a temperature of 18 ,,. 20 ° C. The attack on tomato plants is determined after 5 days. The evaluation values ​​obtained are recalculated in percentage attack. 0% represents the absence of attack, 100% means that the plants feel completely-attacked.

In this test, the compounds resulting in the preparation examples 1, 5, 8, 16 and 17, according to the invention, show a very good activity, which is clearly superior to that presented by the compounds known in the art.

The present advantage of the present invention is that it elaborates a process for the preparation of some carbamoiithiazolyl-0, N-acetyl, of formula I of the above, whose superior fungicidal activity and toxicity are relative to that of the present invention. crop plants, broadens the range of fungicidal egg products.