CA1195992A - 1,2,4-triazol-1-yl-propionitrile derivatives, their preparation and use - Google Patents

Abstract

Abstract 1,2,4-Triazol-l-yl-propionitriles of the general formula in which R represents an aryl radical optionally substituted by one or more of the same or different sub-stituents selected from halogen atoms and (C1-C4)-alkyl, (C1-C4)alkoxy, (C,1-C4)alkylthio, trifluoro-methyl and nitro groups and represents a (C1-C10)alkyl, (C3-C8)alkenyl, or (C3-C8)alkynyl radical, or a phenylalkyl radical optionally substituted by one or more of the same or different substituents selected from halogen atoms and (Cl-C4)alkyl, (Cl-C4)alkoxy, (C1-C4)-alkylthio, trifluoromethyl and nitro groups, acid addition salts thereof with inorganic and organic acids, a process for the preparation of these compounds, and biocidal agents containing them are provided.
The agents have a herbicidal, fungicidal, plant growth-regulatory action and also a bactericidal action and may be used for treating seeds, living plants and crop areas and also animate and inanimate substrates subject to bacterial attack.

Description

~3~

1,2,4-triazol-~yl~propionitrile derivativec~
their preparation and use.

The present invention is concerned with new 1,2,4-triazol-1~yl~propionitrile derivatives, their 5 preparation and use as biocidal agenkx, esp~cially those having a fungicidal, herbicidal, bactericidal and growth regulating action.
Imidaæolyl-propionitrile derivatives having a fungicidal action ~re ~lready kno~n ( see German Offenlegungsschrift ~o. 26 04 047). These, however, have a relatively narrow range of action, which is unsatisfactory.
: It is an aim of the present invention to provide new propionitrile derivatives that offer a wide variety of possible applications t especially in the field of plant prote~tion, and have a broad fungicidal range of action.
The present inYention provides a compound of the general formula ~0 R C _ C~
C~

in which ,...........

s~

R repre~ents an aryl radical ~hich i~ unsubsti~uted or substituted by one or more of the same or different ~ubstituent~ selected from halogen atoms, (C~-C4)alkyl group~, (C~-C~)alkoxy group~
(Cl-C~)alkylthio groups9 trifl~oromethyl groups and nitro groups, and R~ represents a (C1~C10)alkyl radical~ a (~3,C~)alkenyl radical, a (C3-C8~alkynyl radical or a phenylalkyl . radical which is un3ub~titute~ or substituted by one or more of the ~ame or different ~ubstituent~
selected from halogen atoms, (C~ C4)alXyl groups, ~C~-C4)alkoxy groups, (C1-C~)alkylthi 3 groupsO
trifluoromethyl groups and nitro groups, 15 or an acid addition salt thereof with an inorganic or oxganic acid.
The compounds according to the present invention are, in the broadest sense, biocidally active, but are distinguished in particular by a fungicidal action in 20 which they are ~urprisingly superior to known activ~
substance~ of analogous constitution and mode of action~
The fungicidal action ~urprisingly extends to action against fungi which attack different systematic positions in plants. In th~ treatment of parts of the 25 plant above 50il level the cornpounds of the present invention can give protection agai~st wind-borne pathGgen~. To control seed-tran~rmtted pathogens, the - \
~s~

compounds can also be used for treating seeds them~elves. In addition, these compounds can act systemically, that is to say they can be taken up by the roots of the plant, for example after being app1ied to the seed, and be tran~ported to the parts of the plant above soil level to protect those parts against pathogens.
Further actions e~hibited by compounds of the present invention which may be mentioned are growth-regulatory action and bactericidal action.
Owing to the broad range of action which they have been found to possess, the compounds are suitable not only for the protection of crop plants but also for the general protection of materials and for the control of/ for example, microbes causing disease in humans and an;m~l5, and, as a result, their possible applications are very varied.
As may be appreciated, the f i~lds of application in which the compounds exhibit outstanding actions can vary in accordance with the specific meaning of the substituents. Thus, they can be u~ed as fungicides, plant growth regulators or bactericides.
An alkyl group present in a compound of the invention may ~e a straight-chain or hranched-chain alkyl group. Similarly an alkenyl or alkynyl group present in a compound of the invention may be a straight~
chain or branched-chain alkenyl or alkynyl groupn ~ ~\

In the compounds of the general formula I
R may repre~ent, for ~xample, any of the following groups:
phenyl, 2-fluorophenyl, 3-fluorophenyl, 4~fluorophenyl, 2-chlorophenyl, 3- hlorophenyl, 4-chlorophenyl, 2-bromophenyl t 3-bromophenyl, 4 bromophenyl, 2-iodophenyl, 3 iodophenyl, 4-iodophenyl, 2,4-dichlorophenyl, 3,4 dichl~ro-phenyl, 2,6 dichlorophenyl, 2-methylphenyl, 3 methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, ~-ethylphenyl, 2 propylphenyl, 3~propylphenyl, 4-propylphenyl, 2 isopropylphenyl, 3-isopropylphenyl/ 4-isopropylphenyl, 2-butyl-pheny:L, 3-butylphenyl, 4-butylphenyl, 2-sec.-butylphenyl, 3-~ec~-butylphenyl, 4-sec.-butyl-phenyl, 2-~ert.-butylphenyl, 3-tert~-butylphenyl, 4~tert~-butylphenyl t 2-methoxyphenyl, 3-methoxy phenyl J 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxy-phenyl, 4-ethoxyphenyl, 2~ methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-ethylthio~
phenyl, 3 ethylthiophenyl, 4-ethy~thiophenyl,

2-trifluoromethylphenyl, 3-~rifluorome~hylpheny 4 trifluoromethylphenyl, 2-nitrophenyl, 3-nitro-phenyl, 4-nitrophenyl, 3-fluoro-4-methoxyphenyl;

3-chloro-5-nitrophenyl, 4-chloro-2~fluorophenyl, 3,495-trimethoxyphenyl, and 2-chloro-2-nitro-phenyl and R~ may repre~ent, for example, any one o~ the following groups: (C1~C10)alkyl, for example methylg ethyl, propyl, butyll pentyl, hexyl 9 heptyl, octyl, nonyl, decyl, isopropyl, 2,2-dimethylprop-1-yl, 3,3-dimethylbu~2-yl, (C3-C8)alkenyl, for ex~nple allyl, 2-buten-1-yl, 3-methyl-2 buten-1-yl, hexenyl, heptenyl, octenyl, phenylalkyl, for example benzyl, 2 fluorobenzyl, 3-fluoro-benæy~, 4-fluorobenzyl~ 2-chlorokenzyl, 3-chloro~
benzyl, 4-chlorobenzyl, 2-bromobenzyl, 3-bromo-benzyl, 4-bromobenzyl, 2 3 4-dichlorobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, 2-methyl~enzyl~
3 methylbenzyl~ 4-methylbenzyl/ 2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-trifluoro-methylbenzyl, 3-tr.ifluoromethylbenæyl, 4-tri~
fluoromethylbenzyl, 2-metho~ybenzyl, 3~metho~y-benzyl, 4~methoxybenzyl, 2-ethoxy~e~zyl, 3-ethoxy-benzyl, 4-ethoxybenzyl, 2-propoxybenzyl, 3-pro-poxybenzyl, 4-propoxybellzyl 9 2 butoxybenzyl, 3-butoxybenzyl, 4-butoxy~enæyl, 2-methylthioberlzyl, 3-methylthiobenzyl, 4-methylthiobenzyl, 2~ethyl-thiobenzyl, 3-ethylthiobe~zyl, 4-ethylthiobenzyl~
2~butylthiobenzyl, 3-butylthiobenzyl, and 4-butyl-thiobenzyl.
An aryl radical repre,sented by R i~s preferably a phenyl group, especially an alkyl or halogen-substituted phenyl group.

S9~;~

A radical represented ~y Rl is preferably a ~C~-Clo)~lkyl group or an allyl group.
I~oxganic and organic acids for the formation o the acid addition salts of the present invention which may be mentioned by way of example are hydrohalic acids~
such a~, for examp e, hydrochloric acid and hydrobromic acid~ phosphoric acid, sulphuric acid, nitric acid, especi~lly conc~ nitric acid, mono- or bi-functional ~arboxylic acid~ and hydroxycar~oxylic acids~ such as, for example, acetic acid~ maleic acid, ~uccinic acid~
fumaric acid, tartaric acid, citxic aoid~ sàlicylic acid, sorbîc acid~ lactic acid t and also ~ulphonic acids, ~uch as, for example, ~ toluenesulphonic acid and 1,5-naphthalenedisulphonic acid.
The acid addition salts of the present invention may be obtained by the customary salt formation proce~eQ, for example by dissolving a compound of the gener~l formu~a I in a suitable solvent and addi~g the desired acidr A~ an acid addition salt of a compound of the present invention, a hydronitrate salt is preferred.
The compounds of the prese~t in~ention that are distinguished by an outstanding fungieidal action are especially those compounds of the general formula I in which the radical R represent~ any one of the following group~-phenyl, 7-chlorophenyl d 3 chlorophenyl, 4-chloro-C3`~

phenyl, 2,4-dichlorophenyl, 3,4~dichlorophenylO

4-bromop~enyl, 2-~luorophenyl, 4-fluorophenyl and 2-methylphenyl and the radical R1 repre~ents any one of the following group~:
ethyl, allyl t propyl~ isopropyl, butyl and hexyl~
Preferably, of these compound~, there are to be mentioned ~ho~e in which R represent~ a phenylO 4~chlorophenyl or 2-methyl-phenyl yroup and Rl repre~ents a propyl~ i~opr3pyl or butyl group.
~ ha following COmpGUndS according to the inven~ivnha~e been found to have an outst~n~ing action:
2-isopropo~y-2-phenyl-3~ c4-triazol-l yl~-propioni-trile hydronitrate, 2-butoxy-Z-~2-methylphenyl)-3-(1,2,4-tri~zol-l yl3 propionitrile hydronitrate, 2-phenyl-2-propoxy-3-~1,204-triazol-l-yl~ propionitrile hydronitrate, 2-butoxy-2-(4-chlorophenyl)-3-(1 t ~ o 4-triazol~l-yl~-propionitrile hydronitrate, 2 (4-chlorophenyl)-2-propo~y~3 (1,2,4-triazol-l-yl)-propionitrile hydronitrate, 2-i~opropoxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propion-nitrile,

5~

a -2-butoxy~2-(2-methylphenyl~-3-~1~2,4-triazol-1-yl)-propionitrile, 2-hexyloxy-2-phenyl 3~ 2,4-txiazol-1-yl)-propionitrile hydronitrate, S 2~butoxy~2~(4-ch`lorophenyl) 3~ 2~4-tria propionitrile~
2 t4-chlorophenyl)-2-propoxy-3~ 2~4~riazo~ yl) propionitrile, 2-~exylo~y-2-(2-methylphenyl)-3~ 2~4-triazo~ yl) 10 propionitrile hydronitrate D
2 butoxy-2-phenyl-3-~1,2,4-triazol-1-yl)~propionitrile hydronitrate, 2-butoxy-2~(2-chlorophenyl~ 3~(t,2,4~triazol-1-yl~-propionitrile hydronitrate, 2-ethoxy-2-phenyl-3-(1,2~4-triazol-1-yl)-propionitrile hydronitrate, 2-allyloxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propionitrile hydronitrat~, 2-(2-chlorophenyl)-2~propoxy~3~ 2,4-triazol-1-yl)-propionitrile hydronitrate,2-(4-chlorophenyl)-2-hexyloxy-3-~1,2~4-triazol~l-yl)-pxopionitril~ hydronitrate, 2-hexyloxy-2 (2-methylphenyl)-3~ 2,4-triazol-1-yl)-propionitrile, 2-butoxy-2-ph~nyl-3-~1~2,~-triazol-1-yl~ propionitrile~
2-(2 ch~orophenyl~-2-butoxy-3~ 9 4~triazol~l-yl) propionitrileO

5~
., 2~ethoxy-2-phenyl-3-(1,2,4-triazol-1-yt)-propionitrile, 2-allyloxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propionitrile, 2-(2-chlorophenyl)-2-propoxy~3-(1,2,4 triazol-l-yl~-propionitrile.
Th~ compounds ~ccording to the pre~ent invention exhibitO in p~rticular, fungicidal actions but/ at the same timP/ are distinguished by a growth-xegulatory action in a number o~ crop plants~ Further, dep~n~;n~
on the type of plant and the application quantityO
herbicidal effects also are produoed and make possible weed control in such c ses.
Since the compounds according to the inv~ntion can both bring about quantitative and qualitative changes in the plant~ and alter the metabolism o plant~ they are to be classified as plant yrowth regulatorsO which are di~tinguished by the following possible application~:
inhibition of the vegetati~e growth in woody and herbaceous plant~, for example on road~ides, railway track3? etc., to prevent l~lsh growth, 2~ growth inhibition in cereals to prevent lo~ging or snapping off and in cotton ~o increase the yield, illfluencing of branching of vegetative and gen~rative organs in orn~mental and crop plants to increase the amOUllt ~f blo~som or in tobacco and ~5 tomatoes to inhibit the formation of side sh~ots, improvement of fruit quality, for example an increase in the sugar content in ~ugar cane, in sugax beet ox in fruit, and a more even maturation of the crop whieh result~ in higher yield3, 3~
. , -- o --raising of the re3istance to climatic effect~ quch a3 cold and drought~
influenciny of the latex flow in rubber pl~nt~
Other po~sible applications areo development of parthenocarpic fruits, pollen sterility and sex determi~ation, control of the germination of seeds or the pro-duction of buds~
defolia~ion or influenciny of fruit drop to faci-li~ate harvestinq.
Th~ compounds accordi~g to the invention are especially suitable for influencing the growth of Beta (~eet) cxop~ but also have desirable growth-regulatory ; effect~ in cereals, soya and cotton or also generally in plantation crops.
It will be appreciated that not every com~ound will have the same herbi~ida~, fungicidal and/or regulating actions with every ~ype o plant, type o applicationt time of application or concentration appliedO
Depending on the purpose ~f application, the application quantities are generally in the range of from 0.05 to 5 kg of active substance/hectare, but gr~ater applic~tion quantities may be used if appropriate. When two or more cornpounds axe used the range of from 0.05 ~o 5 kg per hectare refer3, of course~ to the total application quantities~

The time of application varie~ in accordance with the purpose of application and the climatic conditions~
The compounds o t~e present invention can ~e applied to seeds, germinating ~eeds (before or after S emergence~, roots, stalks, l~ave~, blos~om, produce or other parts of the plant~ as desired.
Surprisingly, the action of the compounds according to the present inYention i9 broader or stronger than that of known products having the same direction of actionO
In addition to the actions described above, the compounds according to the present inventio~ al50 have a bactericidal action which allows further pos~ible application~. Treatment of animate, for example living plan~s, and ; n~n;m~te ~ubstrates to pro~ect against bacterial attack is thu~ possible.
The present invention accordingly al30 pxovide~
a biocidal preparatio~ which c~mprises at least one compound selected rrom compounds of the general formula I and salts thereof with inorganic and organic acids, in admixture or ~onjunction with a suitable carrier.
The present invention further provide~ a method of protecting a living plant against weeds and/or phytopathogenic fungi andJor of regulating its growth, wherein the living plant and/or the area in the vicinity of the ~iving plant i~/are treated with a compound sel~cted from compounds of the general formula I and ~alt~ thereof with inorganic and organic acid~

.3~
,~ ..

The present invention fuxther provides a method of protecting a crop area against weeds and/or phytopath~-genic fungi and/or of regulating the growth of plant~ in the area, wherein the crop area is treated with a compound selected from compounds of the general fonnula I and salts thereof with inoryanic and organic acids.
The pre~e~t invention further provide3 a method of dressing seeds0 wherein t~e seeds are treated with a compound selected from compounds of the general formula I and salts thereof with inorganic and organic acid~.
The present invention also provide~ a method of protecting a substrate against hacteria, wherein the su~strate i~ treated with a sompound select~d from compounds of the general formula I and salts thereof with inorganic and organic acidsO
The presenk invention further provides a pack which compri~es a compound selected from compound~ of the general formula I and salts thereof with inorganic and organic acids, together with instructions for it5 use as a herbici~e and/or fungicide and/or bactericide and/or for regulating the growth of a living plant~
The compounds according to the invention can be used on their own or in admixture wit h one anothex or with other active substances. Other plant-protective 25 agent s or pest-cont rolling agerlt s or defoliants may opkionally be added~ depending on the desired application~

5~

The active substances of the present invention or mixtures thereof are advantageously ap~lied in the form of biocidal preparations, for example powder~, strewable agent3l granule~, solutions, emulsions or suspension~, with the addition of solid and/or liquid carriers, and diluPnt~ and, if de~ired, wetting ayents, adhe3ive agent~, emulsifiers and/or dispersing auxili~rie~O
Suita~le liquid carriers are, for exampleg water 9 aliphatic and aromatic hydrocarkon~, for example benzene, lG toluenel xylene, cyclohexanone, i~ophorone, dimethyl sulphoxide, dimethylformamide, and al~o mineral oil fractions and vegetable oilq9 As solid carrier~ there are suitable mineral earth~, for ex~mple Tonsil ~a trade marX~, silica gel, talcO kaslin, attapulgite, limestone, silicic acid and vegetable product~, for exam~le meals.
Surface~actiYe substance which may be mentioned are, for examplel calciwm lignin sulphonate, polyoxy-ethylene-alkylphenyl ethers, naphthalenesulphonic acids ~0 and salts there~f~ formaldehyde condensates, fatty alco~ol sulphates and al~o substituted benzenesul.phonic acids and salts thereof.
Where the active substances are to be u~ed fGr dressiny seeds, they may also be admixed with colouring substances to give the dressed seed a clearly visible coloux.

The total amount of the active ~ub~tance or suhstance~ in the various preparations can vary within wide limit~ For example, the ~gents ma~y contain in the range of from approxi~ately 10 to 9~0 by weight active ~ubstance(s), from approximately 90 to 10 by weight liquid or solid carrier~s) and also, if desired, up to 2~h by weight ~urface-active agent(s~.
The agent3 may be ~pplied in custom~ry manner, for ~m~l e with water as the carrier in spray liquor quantities of in the range of from appro~imately ~00 to 1000 litre~/hectare. It is equally possible to use the agents in a s~-called "Low-Volume-Proce3s"
or "Ultra-Lvw-~olume-Process" and to apply them in the fvrm of so-called microgranules.
The following constikuents~ for example, may be used for the manufacture of a preparatio~ of the invention:

A. Sprayable powder a) 40 % by weight active substance 25 % by weight clay minerals 20 % by weight silicic acid 10 % by weigh~ cellulose pitch 5 % by weight surface-active substance based on a mixture o~ the calcium salt o~

5~

~ 5 ~

l; ,~ni n~phonic acid ~d al~l~
phenolpolygl~cvl ethe~s b) 25 % by weight active substa~e 60 % by weight kaoli~
10 5~ b;y ~-eight silicic acid 5 5~ bsr weight surface~ astive su~sta7lces based nn the sodium ~alt of :~met~
o~ e;yltaurirle ~ ~he calcium ~alt 0~ J ~ ~i n~ulphon:ic acid lo . c3 lo ~ by ~eight acti~e ~ubsl;~ce 60 % b~sr ~eight clay mi~eral~
:15 ~ by weight ~ilicic acid 10 ~ ~y weight oell~lo~ pit~h 5 % by weight ~ face acti~e su~3t~ces ba~ed o:~
.,he 30dium s~lt o~ ~-methyl~ oleyl~
tau~ e a~d the ~ci~m sal t o~
1 ~ ~n i n ~ l.phonic ac~id R. Pa~e 4~ ~ by weight act~ive substance 20 5 % b~ weight sodi~L~n aluminium s~licate 15 5~ by weight cetylpol~gl~col e~he~o ~ith 8 moles o:~
ethylerLe o~:ide 2 ~; by wei~ht spindle vil 10 % ~y weight polyeth~lerleglyc~l 25 2~ part~ water C. Emulsion concentrate 25 % by weight active sub~tance 15 % by weight cyclohexanone 55 % by weight ~ylene 5 % by weight mixture o~ nonylphenylpolyoxyethylene or calcium dodecyl~enzene ~ulphonate~
The pre~ent invention further prQVideS a process for the preparation of a compound of the invention, or a salt thereof, which compri~es reacting a c~mpound of the general formula O~

R _ C _ CH2 - Y II

CN

in which R and Rl have th~ meaning~ given above and Y
represents a halogen atom or an alkylsulphonyloxy or arylsulphonyloxy radical which is optionally halogenat~d in the side chain with a compcund o~ the formula ~ - CH
Il 11 HC N
H

or an alkali. metal derivative thereof if desired in the pre~ence o~ a ~olvent and, optionally, in the pre~ence of a ba~e 9~

and, if d~ired, a ~ompound of the general formula I
i~ convexted into an acid addition salt thereof with an inorganic or organic acid and/or acid addition salt i~ converted înto a corre~ponding free compound of the general formula I.
As a halo~en atom represented by Y, ther~ may be mentioned, for ~x~mrle, a chlorine, bromine and iodine atom' as an alkylsulphonyloxy ra~ical repre~ented by Y ther~ are suita~le, for exa~ple a methyl,, ethyl--, propyl~ and trifluoromethyl-sulphonyloxy group, and a~ an arylsulp~onyloxy radical represented by ~ there may be ~entioned~ ~or exampl~, a ben enesulphonyloxy and p-toluenesulphonyloxy group, The reaction may ke carried out bo~h with an exce~s of 1,204-triazole optionally in the presence of a ~olvent and with the addition of a strong base, for example sodi~m hydroxide ox potassium hydroxide.
In additi~n~ a 1,2,4 triazole-alkali metal derivative may be used instead of 1,2,4-triazoleO
Suitable solvents are those which are inert toward~ the reactants, preferably those o~ a polar, aprotic nature, ~uch a~ ~,N-dimethylfonmamide, ,~ ¢~ 3<~

dimethylacetamide, ~-methylpyrrolidone, tetramethylurea~ hexamethylphosphoric acid triamide and k~nzonitrile, but higher boiling point aromatic and aliphatic hydrocar~ons, such as toluene, 5 chlorobenzene or xylene, may also be u~ed~
The reaction tempera~ure may be varied within wide limit~O A temperature in the range of from 10~ C to 200C i~ preferred~ The reaction may be caxried out under normal or exce~s pressure.
The 1,2,4-triazol-1-yl-propionitriles according to the invention are, in general, almost colourless and odourless ~olid substance~O The acid addition - 19 ~
salts derived therefrom are also colourless ~nd odourles~, crystalline compounds. The free base3 are ~paringly soluble in water and more or les~ readily soluble in organic so7vents, such a~, for exa~ple, alcohols d ethers or chlorinated hydrocarbons~ The acid addition salts are to some extent soluble in water and readily soluble in polar organic solvents such as acetonitrile~ N,~-dimethylform~mide~ lower alcohols~
chloroform and methylene chloride.
The following Examp~e.~ illustrate the invention. Unless otherwise specified 9 percentages are given hereinafter on a - weight basis~ -Exampl~ 1 2-Isopropoxy-2-phenyl 3~ 2~4-triazo~ yl)~propi nitrile hydronitrate (Compound no. 2) 0.55 mol of 1,2,4-triazole is added~ while stirring and cooling, to sodium hydride (0.55 mol~ suspended in 50 ml of dry dimethyl formamide (DM~). O.11 mol of 2-isopropoxy-3-methylsulphonyloxy-2-phenylpropionitrile in 50 ml of DMF i~ then added an~ the whole is maintained at a bath temperature of 150 C for 1.5 hours. After cooling, the mixture is extracted three times with 100 ml of ether, the com~ined ether phases are washed twice with water and dried with ma~nesium sulphateO
MgS0~. The ether i9 concentrated by rotary evaporation in vacuo, 50 ml of isopropanol are added to the residue an~, while 3tirring and cooling J 6~8 ml of ~ hJ

- 20 _ concentrated nitric acid are added dropwi~e. After the additon of 80 ml of ether, the mix~ure i9 ~tirred for a further 1~4 hour and then suction-filtered.
Recry~talli~ation i~ effected from isopropanoln m.~. 185-189 C (with deco~po~itlon) Yield: 15 g = 43 % o~ the theoretlcal yield~
Example 2 2 Isopropoxy-2-phenyl-3~(1,2,4-triazol-l-yl~-pr~pi~
nitrile (C~ d no. 3) 10 g of the hydronitxa~e of ~-isopropoxy~2-phenyl-3-(1 t 2,4-triaæol-l-yl~-propionitrile ~btained in Example 1 are di~olved in ~ethanol and 8 ml of 32 %:-~
strength ~mmo~ia water are added~ ~he mixture is poured into water, extracted with ethyl acet~te, dried over magnesium ~ulphate, MgS04, the ethyl acetate i~
concentrated by rotary evaporation in VACUO, a lit~e ethyl acetate and active carbon are added, the mixture i~ boiled briefly, 3u~tion-filtered and again concen tratecl by rotary evaporation. The re~ulting ~olid i~
analytically pure~
m.p. 176-177C
Yield: 6.65 g ~ 83 % of the theoretical yieldO

~ 21 -The Xoll~win~ compounds according to the invention can be prepared in an analogou~ r~anner tc~ that de~cribed in Exal~ple 1 or E~ample 2. "D" under physical con3tant indicate~3 ~decompo~;it~

3{~
~2 -Compound no. N~me of c~mpound Physical c~n~tant lo 2-~xyloxy-2-t2-methylphenyl)-3~
(1,2,4~triazol-1-ylj-prop.ionitrile hydronitrate m.p. 159-162C (D) 4. 2-Butoxy-2 (2-methylphenyl~-3 (102,4-triazol-l~
y7)-propionitrile m.p. 58 62~C
2-Butoxy-2-(2-methylphenyl)-3-~1,2,4-triazol-1-yl) propionitrile ~5 hydronitrate m.p. 158-~61C (D) 2-Hexyloxy~2~ 20 methylphenyl3~3-( 1 ~ 2 J 4-triazol 1-yl)~propionitrile nD40: 1.5121 2D 7. 2-Butoxy-2~phenyl-3-(~2,4-$riazol~-l-yl)-propionitrile hydr~nltrate m.p. 159~1~0C (D3 8~ 2~Butoxy~2~2-chlorophenyl)-3 (1,2,4-triazol-1-yl)-propionitrile hydronitrate m.p. 142.5-i44C ~D~

_ ~3 _ Compound no. Name of compound Physical constant 9. 2-Ethoxy-2-phenyl-3-~1,2,4-triazol-l-yl)-propionitrile hydronitrate mOp. 169-170~C (D) 10. 2-P~enyl-2-propoxy-3~ 2,4-tria ol~l-yl3-pxopionitrile hydronitrate m.p. 178 179 C ~D) ~0 11. 2-~3~Chlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)~propio~
nitrile hydronitrate m.p. ~73-~75~C (D) 12~ 2-Butoxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile m.p. 67-68C
13. 2-Pheny~-2-propoxy-3-(1S2 t 4-triazol l-yl)-propionitrile mvp. 107-108C
20 1~0 2-~thoxy-2-phenyl-3 (1,2~4-triazol-l-yl)-propionitrile m.p. 74~75~C
15 . 2--~Iexyloxy~ 2-phenyl-3- ( 1, 2, 4-triazol~
l~yl )-propionitrile hydrorlitrate m.pO 158~1 60C ~D~

Compound no,, ~ne of compound Phy3ical con~tant 1 ~. 2~ 1ylox~r~2-~enyl-3 r ( 1 ~ 2 ~ 4 txiazol-l-yl )-propionitrile hydronitrate m~p. 145-~47C (D~
1 7 . 2-Butoxy~ 2- ( 4 chlorophenyl )-3-( 1, 2, 4 -triazol-l-yl )~propio nitrile hydro-nitrate m~pO ~ 73-1 ~5C ~D) 1 8. 2-Allyloxy-2-phenyl-3- ~ 1, 2, 4~triazol~
l~yl )-propionitrile m.p. 86-88C
19 . 2-~5ethoxy-2-phenyl 3- ~ ~, 2, 4-triazol-l-yl )-propionitrile m.p. 77-?9C
20 . 2-~Ie~yloxy~ 2-phe~nyl-3- ( 1 ~ 2 ~ 4-triazol-l-yl )-propionitrile ~IIIap~ 58 SOC
21 ,. 2- ( 2-Chlorophenyl ~
2-hexyloxy 3~ ~1, 2, 4-triazol-1-yl ~-propionitrile hydrc) nitrate m.p. 157--1 59C (D) _ . I

~5~
,., ~ ~5 --Co~pous~d no. Narne of compound Physical constant ~2 . 2- ( 2-Chlorophenyl )-2--p~opoxy--3--( 1, 2, txiazol~ yl ~-pro-pionitrile hydro-nitrate la.p,, 138-1 39C~c (D) 2 3 7 2- ( 4-Chlorc:phenyl ) -2-propo~-3-(1 "2,~
triazol-l-yl )-prs-1 S~ pionitrile hydrs:
- nitra~e m.p. 155-1 7~C (D) 24 ~. 2- ~ 4-Chlorophenyl 3-2-hexyloxy-3- ( t ~ 2, 4 triazol-~ -yl )-pro-pionitrile hydro-nitrate m~p. 155-1 5g C (D) 2~ . 2~ Chlorophenyl )-2 ~propoxy- 3 ( 1, 2, 4-triazol-l-yl ~-pro-pionitrile m~p.115-119~
26 . 2-BIltoxy-2- ( 4-chlorophenyl )-3~
( 1, 2, 4-triazol-l -yl )-propionitrile m.p.54-60C
27 . 2- ( 2-Methylphenyl )-~--oc~loxy-3-5 l, ~ ~4-triazol l-yl ~-pro~
pionitrile hydro~
nitrate m~p . ~ 2l3 1 34~C ~D ) 5~3~

Compound no. Name c:~f compound ~hy3ical constant 28......... 2-Decyloxy-2-( ~-methylphenyl ) 3- ( 1, 2, 4-~riazol-l~ propionitrile hydronitrate m.p. 116~1 20C7c ~D~
2g ,. ~- ( 2-Methylphenyl )~
2--oc~rloxy--3~ 9 4-triaæol-l-yl ~-pro-pionitrile nD2C). 1.~930 30. 2- ( 2-Chlorophenyl )-2-~ut~x~ 3- ( I , ~ ~ 4-triazol-l-yl )-pro-pioni~ril.o n~ ~40 1 . 5273 1 5 3 ~ . 2- ( 2-Chlorophenyl )-2-propoxy-3 ~ ~ 1, 2 t 4~
triazol~l-yl ~-pro-pionitrile nD40 t . 5 308 3 2 . 2-Butoxy 2- ( 2, 4-clichl~rophenyl )-3- ( 1, 2, 4-triazol-1-yl )-propioni~rile hydronitrat~ ra.p. 163-1 66C
3 3 " ~ -~3utc~xy--2-- ~ 2 " ~
dichlorophenyl ~-3- ( t 3 ;! ~ 4-triazc)l-l-yl ~-propionitrile m.p,. 53-55C

35~
.. , ~
_ 27 ~
Compo~md no. Ncl~e of compound Physical constant 3~. 2~ lo~y 2-(2,4-dichloro-phenyl)~3-(1,2,4-triazol-l~yl)-pro-pionitri~ m~p. 104-1 07C
35. 2-(3,4~ichloro-p~enyl)-~-propoxy-3-~1,2,4-triazol-l-yl)-propionitrile hydronitr~te m.p. 1~ 155C (D~
36. 2-(3,4-Dichloro-phenyl)-2-propoxy-3-(1,2,~-triazol-l-yl)-propionitrile m.p. 60-66C
37. 2-~3,4-Dichloro-phenyl)-2~hexyloxy-3~(1,2~4-triazol-l-yl)-propionitrile hydronitrate ~.p. 166-168~
38. 2-~3~4-Dichloro~-~henyl)-2-hexyloxy~
3-(1,~,4-triazol-1 yl)-prQpionitrile nD40 1.5240 25 390 2-~4-Fluorophenyl)-2~pr~poxy-3-~1,2,4-triazol~l-yl~pro-pionîtrile hydro-nitrate m.p~ 172-175C [D~

3~43~

~ 28 _ Compound no. ~ame of compound Phy~ical con~tant 40 n 2-(4~Fluorophenyl~-2-propoxy-3-(1,2,4-triazol-l-yl)-pxo-pionitrile m.p. 98-100C
41. 2-Butoxy-2-(4-~
fluorophe~yl)-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate m.p. 173-175~C (D~
42. 2-Butoxy-2-~4-fluorophenyl)-3-~1,2,~-triazol-l-yl~propionitrile m.p~ 56-58~C
43. 2-(2-Fluorophenyl)-2-propoxy-3-(1 t ~ ~ 4~
triazol-l-yl)-pro-pionitrile hydro~
nitrat~ m~p~ 150-153~C (D) 44. 2-(2-Fluorophenyl~-2-propoxy-3-(1,2,4-triazol-l-yl)-pro~
pionitrile m.p. 66-69C
45. 2-Butox~-2-(2-fluorophenyl)-3-~1,2,4-triazol-l-yl)-propionitrile hydronitrate m.p~ 138-143& (D) 3~

Compound no~ ~me of compound Phy3ical con~t~nt 4~0 2-~utoxy-~-(2-fluorophenyl3 3-(1,2,4-triazol l-yl)-propionitrile m~pO 76-79C
47~ 2 (2~Fluorophenyl) -2-h~xyloxy 3-~1,204 triazol-l-yl)-pro-pionitrile hydro-nitxate m.p. 134-137 (D) 48~ 2-(2-Fluorophenyl)-2-hexyloxy-3-(1,2,4-triazol~l-yl)-pro~r pionitrile m.pO 58-60~C
15 49. 2-(4-Bromophenyl~-2-propoxy-3-(1,2,4 triazol-l~yl)-pro-pionitrile hydro-nitrate m.p. 150-153C (D) 20 50. ~-(4-Bromophenyl)-2~propoxy-3-~1,2,4 triazol-l-yl)-pro-pionitril2 m.p. 118-121~C
51. 2-~4-Bromophenyl~-2-hexyloxy-3-(1,2,4-triazol~l-yl)-pro-pionitrile hydro-nitrate m~pO 161-164~C ~D~

t,~-' 7 Q~

- 30 _ Compound noO Name of compound Physical con~k~nt 52. 2 (4 Bromophenyl~-2-hexyloxy-3-(1,2,4-triazol-l~yl)-pxo-pionitrile m.p. 60-62C
53. 2-(2,4~Dichlo~o phenyl)~2-propo~y-3~ 2,4-triazol~
l-yl)-propionitrile hydronitrate m.p. 166-170C (D) 54. ~-(2,4-Dichloro-phenyl)-2-propoxy-3~ 2,4 tria~ol~
l-yl)-propionitril~ m.p~ 61~63C
55. 2-~2-Methylphenyl~-2~pentyl~3~(1,2,4~
triazol-l-yl)-prs-pionitrile hydro-nitrate m~p. ~51=~54C (D) 5~- 2 (2-Methylp~enyl)-2-pentyl~3-~1,2,4-triazol-l-yl)-pro-piGnitrile ~ 4~: 1.5~1 57. 2-(4-Methylphenyl)-2-propoxy-3~ 2~4 kriazol-l~yl)-pro-pion.itrile hydro~
nitrate m~pO t70~171~C (D~

~9~

Compound noO Name of compound Physical con~tant 58~ 2~exyloxy-2~(4~
methylphenyl)-3-(1,2,4-triazol~
yl)-propionitrile hydronitrate m~p. 177-1 8~C ~D) S9~ 2-(4-Methylphenyl)-2-propoxy-~-(1ç2,4-triazol-l~yl)-pro-pionitrile m.p. 1 20 - 124&
500 2-~exyloxy-2~
methylphenyl) 3-( 1, , 4-t~iazol~l yl)-propionitrile n~400 1.5065 15 61. 2~But~xy-2-~4-methylphenyl)-3-(1,2,4-triazol-1-yl)-propionitrile mOp~ 71-73C~

~ 32 -The 3-aryl- and 3-alkyl-sulphonyloxypropionitrile~
of the ge~eral for~ula II in which Y repre ent3 respectively aryl~ and alkyl~3ulphonyloxy which are to bP used as starting materials ha~e not hithexto been 5 described in the literature.
~ hey may be obtained by hydroxymethylati~gO by methods known ~ se, phenylacetonitriles of the _ general formula - Rl R C~ III
C~

in which R and R1 have the meanings given a~ove, some of w~ich are known or can be obtained by method3 known E~ se (cfo for example Rubin et al. ! JACS 67, 192 f (19~5), Hess et a~., Ber~ dto chem. GesO 50, 394 ~1917))or by rea~ting the 3-hydroxypropionitriles of the general formula R ~ C~ _ O~I IV

CN

with a suitable sulphonic acid derivativel for example, a sulphonic acid chloride, optionally with the addition of an acid binder~ The hydroxymethyl compounds of the general formula IV have not hitherto 3~;~

been k~o~ ~rom the literatu:rei The mar~u~acture of a Btl3:rt~;, material is des-cribed belo~
~S-Meth~rlsulphon~ 2-phen~1~2-proPo:~-Pr~ ~ionitrile 27 g (00154 mol) of 2-p~e~ propo~y-aceto~ .
~itrile are d*ssol~rea in 120 ml of p;srridi~, ~d la;,~ g ~0~,614 mol~ o~ paraformaldehyde are addea~ To ~
su~perl~ion~ 7.7 ml o~ tet;rabutylammonium h;yaro~:ide (T~0~) are added as a 40 ~ ~tre~th sc)lu~io~ wh~l~
~0 cooling with ice and the whole is m~ ed thoroughl~ by srigorous B'GirT~g. ~fter a fe~ hours (~1~ morLLto~i~g), the mixture i~ poured i~ltC ice~water allG e~ctracted wi Ith ether,, The ethe~ p~se i~ ~ashea wi~h dil~te hydr~c~loYic acid and the:r~ with ~di~n chloride ~ol~-5 tiorl ~d dried over ma,gDesium ~lalp~atel. ~ter re-mo~ing ~he dryi~lg age~t by iiltrati~n a~d co~centrat-ing by rotary evaporatio~ in vacuo, a colourles~ oil reln~;nF~ beh~:Ld which is fou~d to be homo~eIleo~s according t~ t~in layer chromato~ph~ a~ caD be 20 *ur~her prooes~ed Wit~lGUJt further puri~icati~e, Yield~ 28.4 g = 90 ~ o~ the theoretical ~eld of 3 hydro~y-2 pl~exlyl-2-propo~ propio~tril~
~D D 1~ 5027 28 g ( O ~ 6 mol ) OI 3-hydro~y-2~phe~yl-2--pr~
25 po~y-propionitrile are dissolved i~ 200 ~1 of toltle~
and 19,D5 g ( 0~171 mol) of meth~e3ulpho~1 c~loride are added~. ~t lO~C, 18,.6 g (0,,18~ mol~ OI t~ Le~h;yl I

9~
3~, amir~e are added dropwi~e. The mi~ure is sti~red for 30 minute~ at room temperature9 Ii~tered ~rom the precip~tated triethylamin~ h~drorhloride and co~ce~-tratedO ~he re~iaue i~ taken up ~n ether~ ~a~hed ~ith 5 ~?ater~ driea over magnesium sulphate arld c~rlcentrated.
~he oily re~idue i~ f~ d ts be p~re accord:Lng to th~
7 a;srer chromatograph;~O
~ielda 32~27 g - 86 ~ OI the theoretical ~ield o~ 3-me~h;yls~alpho;~yl-2~phe2:ly?-2 propo:~y-propio-0 nitr;l~
rlD20: 1. 5QOS) ~ he following e:~empla~ emb~dime~t~ illustratethe po~ible applicatio~s o~ the compo~d~ acco:rd~g to the ~ventio~) in the ~orm o~ the preparatioII3 5 menti onea abov~O

~amPle E:f ~ect OI prophylactic leaf treatme~t ~gain~t true milde~r ~rYsiphe ~r~min;æ ~ barley irl a greenho~
~oung barle r plaD~ at the Iir3t lea~ stage were 20 ~pray~d u:llt~l drippi:~g wet with the stated concentratio~
When the spray coating~ had dried9 the treated plant~
a~d also untreated co~trol plants were inoculated with d~ mildew spore~ by bei~g ~tr~ked ~ith in~ected plants. The te~t pla~t~ were then cu:Lti~ted i~n a 25 greenhou~e a~ appro:~imately 20 to 22C and; a~ter o~e ~ee ,, ~ere E1~18e~19~1l *or the RercerLt 3ge attack of ~m 3~ ~

the lea~ ~ur~aceO ~he fungicidal e~fec~ WEL8 ca:Lcu-lated a~ ~ollow~

100 ~ttac3~ ~ treated O lO0 _ % eE~f~ct;
httack in urltrea~ed 5~he compounds ~ere us~d P9 20 ~6 ~tren~th ~ormu lation~ .
Compow~d accord~ Er~ he ,E~r~m;n~
t~ the in~elltion ~oO ~ effe~t 5~0 ppM ILOO ppm;~
1 lOO 95 2 ~00 ~9 100 ~Oo 4 10~ 100 lOû ~5 1 5 6 lOO 94 7 lOO 100 8 l~O lO0 10~ ~

2~ 11 100 9 1~ 100 1~
1~ 100 100 14 ~OO 100 1~ 100 100 1~ 10~ 10 1~ 100 ~ 0 18 1(~

Compvu~d accord~ng :~iphe ~mi n-;
to the i~Yentio~ ~Jo~ f:e~ct ~00 ppm 10~ pp6 19 10~:) 10 )0 9~
~00 1~0 23 109 1~)0 2~ 100 0 ~5 100 26 1(10 ~8 100 95 3C) 10~ 100 31 10~) 100 33 100 lt)O
34 1~30 10~
3~ 100 100 36 lbO 1(:~0 38 ~ 0~
41 100 1~0 ~2 100 lQO
44 100 ~ ~0 ~8 1(~ 95 49 100 lC)~) ~ 10 51 lûO 10~

s~

Compound according:E~rvsiphe ~ram:lnis t~ the i~er~tion NoO ~ eXfect 50û ppm 103 ppm 53 1(~0 100 0 ~0~
' 100 1~0 ~7 1~0 l~û

5~ 100 :1 00 1 O 60 10~ 100 ~1 100 100 amPle 4 ~ffect of prophylactic lea~ treatme::Lt agai~L3t Er~siphe cichoracearum in go~ -plant~ ~ a greenhou~ -~ourd pla~Lts sprayed u~til drippi:clg ~et ~ith the ~tated concentrations ~ere ~oculatcd9 aIter the ~pray coati~g had dri~at by being du~ted with d~ milde~
~pores o~ :E~}siphe cichoracearum a:~d i:~lcubated toge~her ~.h inoculated untreated co~trol plarlts i3~ a g~ee~-20 hou~e at 24C. ~ter o~e ~e~k~ the ~urXace area a:fIected by milde~ a~ a percentage OI the en~ire lea~
~urface ar~a was estirllated9 ~he fungicldal effect ~as calculated as f ollow6:

100 100 o ~ttack i~ treated = ~, eEf~c~;
httack i~ untreaJçed ~he letter "~ the fol~ ow~ng table denote~

~s~

3~ ~

thal; th~ iungicida~ ac~ion co~d al60 be ~s~e~ed the growth of the plant~ ( a~ter treatme~t~ ~nd wa~ .
xound to be positive~ Tha~ is to sa;sr, the act.ive ~ubst~ces ~re tran~ported s:~ste~icall~ in the addi-5 tio~al growth ~d showed one hu~dred per ce~t aetio~
i n Rt mildew ~n that grow th al800 The compoulld~ accordirlg to the inventio~l were used a3 20 5~ s-~rength formulati~n~0 Compou~d according ~ lph~ cichoracear~m ~o to the in~ention 15~o~ ~ effect 250 ~5 5 2.5 0.5 ppm 1~08 10~8 10~
100~ 1005 lOOs 3 10û6 100~ 06 4 100~ 1~0~ 100 10~ 1008 10~

6 1008 1~)09 100

7 ~00 100 1~0

8 . 100~ 9E~ 100 . 9 100~ 1008 100 100~ 10~ 10~
11 100~ lOOs 100 12 10~ 100 13 100~
1~ 1008 1008 100 1~ 100~ 1~0 10~
1~ lûO~ 100 99O 5 .2~

Compound accordingErv~iphe cichoracearum the ~ent i~ eII e ct 25C) ~ 2~g45 PP~
17 ~0~ 1008 1~0 1~ 10~)~ 100 19 100~ 100 97 0~' 100 9~
~2 100~ 103 1 00 0 ~7 l~)Os 2g ~.00~

39 l~û~
1 ~ 40 10~8 ~ lOûs lC~
4~; 1008 ~ ~6 100 ~:~ampl~ 5 :E~fect ~%) of prophylactic lea~ treatment aga~n~t Helmintho~porium teres (= P~reno~hora tere~3, net blotch disea~e, in barley Yo~g barle;y plant~ at the fir~t lea~ stage were ~pray~d until dripping ~et with the atated co~centra-tion~. When the ~pray coating~3 ~ad dried, the treated 5~
.

-~ 40 ~

plant~ and untreated control pl~ta wzre ~prayed ~ith a ~u~pensio~ o~ ~he conidio~pores of He:Lmintho~orium teres a~d :incubated ill a moi6t chamber ~or 2 day~ at ~rcm 20 to 22CC., ~he pla~ts ~e~ç then culti~ated in 5 a gree~iholl~e at 20 to 22ar O~le ~ek a:~ter ~oculatioxl, the percPntage attack of the les:~ sur:~ace~ wa~ no~edl, ~he f~gicidal e~ect wa~ calculated a~ ~ol:lo~o ~ttack i~l treated . 100 100 ~ ef~ect ~ttack i~ untrea~e~

~ he compound~-were used a~ 20 ~ strength :forml:Lla ti~n~"

Compou~d according Hel "~ tho~o~ium teres to the in~er~tion ~0~D ~ e:ffect 5G0 ppm1 00 ppm 10 ppm 2 l~0 lO0 lO0 3 lO0 ~ :)0 ~() g5 90 l~0 lO0 6 9~
7 9~ 90 1~)0 8 2~ lO 95 g5 12 94 9C) ~1~5~

Compou~d accord-~g Helmintho~pori~m teres to the inve~tion ~o,, ,~ effect 500 ppm lûû ppm 10 ppm 1~5 92 85 14 ~39 8~) - 15 94 9~

18 100 7~) 1 0~9 9~
7~) 23 . ~35 ~, 9~ go ~ 9~ 95 1 5 2~ 80 :E~am~le 6 :liifect o~ proph~ylactic leaf treatmell~ agai~st dwarf ~ Puccinia horde:~ in ba:rley in a controlled cl~mat~
20 plænt grow~h chamber You~g barle;y p:La~t~ at the ~i~st lea~ stage were sprayed until dripping ~et with the ~ta ted conce~tra~
tion9~ When the spra~ coati:~gs had dried" the treated pl~nts and untrea~ed c~:~trol plants were ~culated b~y be:ing ~troked with plan~s ai~ectea by dwar~ rust and placed ~ a plant grow th c~m~er~ ~t ~ 5C, and in almDst moi~turesaturated air ~or the first tw~ day~, ~5~3~
.~

~2 ~he pla~s were culti~rated ~or 10 day~O ~e per-ce~tage propor~ion OI the :Leaf ~urface attacked b;y ~ust ~ the~ :~oted~D ~h~ fu:ngic~dal effect wa~ calcu~
lated as follOW8:

Atta~k i~ treat~d ~, 101~
; e*feot ~ttaek ~n ~trea~
'~he compo~ds wer~ used a~ 20 ~ ~tre~gth ~rm~a~
t~ons~, o Compound . according to the invention ~o., Placcinia hordei ~ ef~ect 500 ppm 100 ppm 20 pp~
1~ 77 1 5 2 ~0 ~3 100 1~0 94 . 6 100 9~
2~ 7 10~ 98 E~9 8 10~ 34 94

9 80 ~0 100 98 ~4 12 ~
1~ ~39 14 ~5 80 ~5~

-- ~3. --C~mpsu~d according . .
to the inventinn Ii~ ccln a hordei 5C0 ppm 100 ppm 20 p~m ~. 7~3 ~7 100 100 1 ~ 9~3 1~ 95 ~35 21 1~) :) 7 0 22 1~0 100 ~4 90 7~
9 :) gO

5 30 ~;
31 g7 ~am~le 7 ~ctio~ n~t Pseudomvnzs ph~3eolicola, the cause o~
halo b~ight in bean~; ~ itro Biomalt agar ~as r~oledj after heat st~r~ ation9 t~ appro~imatel;sr 45C aIld was then poured, together with the te~t ~ubatance~ which had been m~:ed together i~ a~ aqueou~ preparatiorLp ir~to plast~c~ petri dishesO
Whe:~ the nutrie~t medilam had ~et, the dishe~ o:f treated agar alld a:Ls0 di~hee cont~;nirl untreated agax a~ a co~trol were inoculated ~ the cen~re by mean~ o~

--- 44 ~

inoculat:ing lo~p with a suspe~ion of the halo bli~ht pathogen Pseudomonas ~haseolicola. ~he di~he~ were therl incubated at ~2C. ~Xter 2~ ~eek~, the radial E3pread o~ the colo~e~ of bacte~ia which had grG~I
5 were mea~ured. ~om the ~verage Df t~o repe~itio~s per te~t 3ample9 the bact~ria inhibi.ti:~lg action wa~
calculated as :~OllC~7E3., l~adial growth in treated O lOû = ~% ~h biti~
R~ growth i~ urltreatea The compoundæ. were uæed a~ 20 % stre~gth ~o~nula tionse, Compo~d according 5~ action ~ith 250 ppm to the i~ention N o O acti~e E~lab~ta~ce co~centratio:a 2~ 66 20 :Example 8 Act~ y o~ su}:)stance~ ln va~?ur f O~L again~t FIelminthos~orium teres in barley in a greenhouse~
To determine thevapo~lr acti~ity, a po~ Cont~nin~
appro~cimatel~r 20 barley seedlings ~it.h the second lea~
~5 be~ nning to appezr was placed bet~eerL ~ pots oi barley OXI which a d:~ ~p~;y coatillg ~ad dried ~ter a dripping wet treatmen~G. The drip~ing wet treatme~t 5 ~ ~ ~
-- 45 ~

was carried out at arl active ~ub~tance concentration o~ 0;,~ su~pensiox~ of the co~dia o~ the net blotc~ pathogen Eelmintho~p~rium tere~, prepa:red with a~ aqu~ou~3 ~o~ution o~ 0.,05 5~ ~odi~m oleate alld 0.0~! ~
5 gela~ine and adJ~sted to 10091:)00 ~p~re~; per m~ ;tre9 ~a~ aprayed over ~11 three p4t~ in each test ~amp3~eO
~ter spraying o~ the ~pore~, the three pots i~ ~ach te~t ~ample were enclo~ed in a polyethylene bag ~or three d~ya a~d kepg ~der gree~:house c~xlditic:~3 o~
appro:~:imately 20Co The bags ~ere the:l:L opened ~y cuttin~ them at the lev81 o' the leaf tips" ~ter 13 days ~ the num~er o~ net blo~ches per pot ~aa courltedO
m thi~ the :f~gic:~dalvapour action wa~ cal~ ed as ~ollow~:

net blotches o~ e:~:pos~d barley ~ 100 = ~ actio~L

~et blotche~ on u~e g:po~ed barley ~he substar~ces according to ~:he in~e~tiorl were u~ed a~ 20 ~ ~tre~th ~ormulati3ns. ~11 vapcur e~s-i!O posures could be tolerated by t}:Le plants.

Compound according ~ effect to the lnventio~ ~o~.

1~0 I

_ 46 ~--Compotand accordi~g to the ixaventio~ No" % ~f~e~

:L~ 8 5 Com~arlson a~ent 1- (4--Chloropheno~ 3 9 3 dlm~thyl~
1-(19,2~4 tria~ol-l-yl~ bu~rlon~ 86 :Exam~l~ 9 Sy~temic e~ect OI ~oil treatme~t beiore emerge~ce ~in~t ~ugar b~et mi:Lde~ :Ervsiphe pc>l~o~ ~ a gree~
house Pla~ pot s~rn with BUgar ~eet were ~prayed with 0~,3 kg o~ actl~e substance per hectare a~d placea be~
~ide u~trea~ed pot~ in a greenho~e a~ appro:;:imately 20C. ~fter the beet plants had emerged (12 to 14 per po1;~ ~ a ~aitirLg period ~as observed u~til the ~ir~t two trlle le~es had de~eloped a~d the plants were the~
in~culated b~ being dusted with the dry ~pore~ o~
true beet mildew ~ siphe Pol~onil ~hree wee~
2c~ ~ ater ~ eekæ a~ter æoil treal;merlt~ the Attack oi the lea~e~ was a~sessed, T~e ~ungîcidal effect c~uld ha~e been achi eved only a~ a re~ult of the substance~
be~g ab~orbed v~a the plant roots arld was calculated a~ ~0110~30 25 . Attack ~ treated ~
eI:~ect ~ttack ~n u~.treated I

5~
. .

~7 ~ he compound~ were u~ed as 20 ~ strengt~ formula~
tion~ 11 treatments ~ere ~ou~d to be tolerable the pla:zlt6 and res~lted ~ mo:re vigorou~ ~d more compact gro~h in comp~iso~ wit~ the untreated co~trol~

5 Compound according to the inventio~ ~ot. ~fe~
1~ 10

10 E~ample 10 Soya and wheat ~ere sprayed i~ pr~emerge~ce with eml:L18iO:!18 OI the test ~ub~tance~ he q~Pntit~ applied was appro:gimately 2 kg o~ active substarlce~hectare.
The pla:~-t8 were then cu:Lti~ated in ~ gree~ouse and 5 m~a~red ~ter th~ee week~O
~ he recorded perce~tage growth inhibi~io~ iB
given iIl the ~able~

Oompound according Gro~th inhil~i~ion 1~ %
to the ~ve~tio~ Nc~o ~o;ya Wheat ~2 ~3 g 0 17 1~ 4 ~4 25 14 17 2~, t~
....

Compo~nd accord~ Growth inhibition to the i~ention ~ S~a Wheat 18 13 1~
22 6~ 21 ~7 2~ 35 24 Com~ariE;on com~ound 1 o 2-Chloro~th;yl~r:~neth;yl_ ammonium chlor~ de 0 17 It will be ~3ee~ t~t 2 as a rale, the ac~io:~ c:f the compou~d~ accord~g to the i:~entiorl iB stro:z~ge2 than that o~ t~e compari son comp~nd.

5 ~amPle ~1 Rice was treated i~ pre-emerge~oe with the com;~
pounds according to the invention irL application quantitie~ o~ 2 kg of acti~e æub~.,ance~hec~are~, ~ter three weeks ' cultivatio~ in a greenhou~;e, the per-20 ce~tage gro~h inhibition ~as dete~minedO
Thi~ ls sh~wn in the ~able ~ompound accordingGrowth i~hlbitio~
to the ~nvention ~oO
22 ~1 2~ 7 ., I

5~

_ 49 _ Gompo~d accordi~lg t~ the inve~tion ~o.Growth inhibitior Coml~ari~on comound 5 2-Ch:Loroe~hyltrimethyl~
ammon:ium chloride O

~ he growth inhibition b;y the compounds accordi3:~g to the in~erltion was not achieved by the comparison compou3~d with the applicatio~ used her~.

Exam~le 12 Sugar beet ~a~ sprayed ln pre-emergence with all appli.cation quantity of 2 k~g of active ~ub~tallce~hec;
tare0 T~e perce~tage ~ro~rth ir~ibition a~d the colour o~ the pl~ts a:fter three ~eek~' cultivatiorl in a 5 g~e~hou~e ~ere recordedl, ~ he re~ult~ are sho~m in the following ~bleO

Compound accordi~g to the i~ention ~og ~ro~rth inhibition ~ ~ Coîou:r g ~ 3~ 1 1~ 22 ~5~¢~
~ 50 ~ompo~d acoordirlg t~ the invention NoO Gro~th i~h~bition ir~ lour 13 41 e~
14 4~ 0 1~ 53 17 ~
:1 ~ . 22 ~9 3 2~ ` ~7 1~ 2~ 6 ~2 ~7 3 ~3 2~ 22 26 ~7 2 ~omParison a~ent 2 Chlsroethyltrimethyl ammorlium chloride O O
~ Eey to colour: O ~ - as control 1 = i~tenBe green 2 - dark g:ree~

~he oompotmds according to the invention a~fect the gx owth of the beets whil~t the same is not achieved bsr the comparisorl c~mpound i~ the applica'Gio~ used here~.

~xam~l ~ 13 fect of propl~ actic leaf treat!nent agairL~t th0 lea~
~pot pathogen Fusarium culmorum ill Italiar~ millet ( Penni~etum .~:laucum~ ~ a greeI~ou~
~o~g millet plant~ ~appro~ ~ate~y ~0 pe~ po~
with the ~eco~ld lea:F be~;nni~f~ t~ appear were ~pra~ea u~til drippi~ wet with the ~tated concent~atiorl~0 When 1the ~pray coa~Ging~ had dried9 the treated pl~n~G~
arld untreated co~rol pl~ts were spra sred with a s~6-0 pensio~ l~f the conidia of ~sarium culmorum a3ld place~
damp in a greenhou~e ai; approx~ately 22C. ~ter days, the percentage proportion of the leaf ~ ace a l;tacked was e~timated ., ~he lungicida~ effect wa~
cal~ulated a~ f~llo~:

10~ . Attack iQ treated dttack in uIltreated 100 ~ eff ect The compou~d~ accorai~ to the in~e~tion wer~
used a~ 20 % strengih formu:Lation~0 ;~0 Compounà accordi~g 5~ e~ect with to the ixlve~tis:n NoO 500 ppm lOa ppm Compo~a~d according5~ effec~ ~ith to the i~entio~ ~o.500 ppm lûO ppm 16 9~

11 95 1~3 95 1 0 23 1()~ g9 2~ 100 97 2~ 100 9 ~6 98 93 27 9~
1 5 2~ 97 90 ~0 97 90 31 100 ~8 ~am~le 14 ~ect o~ proph;~rlactic lea~ ~reat~erLt again~t -the 2C) lea~ po~ ho~en Cercospora betico~a in su~ar beet i~ a gxeenho-a~e Sugar beet plants having a~ lea~t two wel:l de~eloped trae leaveswere spra~e~ ~tîl ~ippi~g wet with the stated concentrations . ~hen the spra;y coat-25 ir~g~ :had dried, the treated pla~t~ and untreated c~trol pla~tfi were spr~red with a ~laspensio~ ~ th~

3~

-- ~3 conidia O:e ~ercoapora beticola and ~ncubated d~mp f or da~ a greenhou~e at 26OC~D ~he pl~nts wer~ ~e~
clllt~vated u~der ~ormal gree~hou~e conditio~ ~o weeks a~ter treatment9 the percentage atta~ wa~
5 a~e~s~d~
~he fungicidal e~fect wa~ calcula~d as fo:Llow~:

lûO o Attack i~ treated 100 ~ - c % effect l~ttac~ in untreated ~he compou~d~ wer~ used as 20 % ~trength :Eorm~l tions~

Compou~d accora~ eIfect with to thein~e~tion 15~o;, 500 ppm 100 pp~
3 lOO lOO
ll 93

12 9~

13 lOo 1~ ~3 17 ~7 2~ 100 96 22 ~30 100 ~3 100 lOC~
24 1~)0 100 ~5~

_ 5~

Compound accord~g~ effec~ h t~ the illvent~orL ~oO 500 ppm 10~ ppm ~6 10~ ~6 27 9~ ~8 ~9 1~)0 9~
OO lOD
~1 100 ~00 0 E:~amp'le 15 :~fiect OI ~eed treatmeD,t ~; nF::t ~eed-borDe He~inthos~ri~ ativllm (ca~e oi f~ot rot) in barleyO
Barleg ~eed in~ectea ~ith :EIelm~ntho~orium ~ati~m was treated ~ith the acti~e ~u~tan~e i~ application quantit;y of 50 m~ OI active 8ubstance per 100 ~amO
2 g o~ treated eeed and 2 g o~ untreated seed were i~
each ca~e ~ow~ i~L pot~ in t~o repet~tio~s and incl;Lbat~d at 15C i~ ~ cl imatic chamber~. ~?rom the ~me that th~
pla~t~ emerged~ arti~icial lighti~Lg wa~ gi~er~ ~ a 12 20 hoar o;ycl~. ~fter 4 week~ l the percentage o~ plant~
~howing ioot rot wa5 determ~ledo ~ the ~ntreated pl~nts were diseased~

Compound accord~
to t~e inven~io~ No. ~ e~ect 4 lC~
9~,5 ~ he compo~and~ were used a~ 20 5~ strength ~ormula~
~ion~ .

:Examp~ e 16 0 :Efîec~ o~ ~eed treatme~t ~i n.q~c ~eed~o~n~ Phoma betae in 8uga:r bee1t.
Sugar beet seed in~ected with P~noma betae wa~
treated with 250 mg o~ active ~ub3ta~ce per lO0 gramp 25 grai~ of treated a:~d OI untreated ~eed were i:n eaoh ca~e ~ow~ iD pot~ i~ fo~r repetition33. Whe:tl the plant~
had emerged, a:rti~icial lighti~g was give2l in a 12 holar cycle,D ~n~il t~e end oi the ~est after 7 ~e~s,, t~e di~ea~ed plan~ were c~ ted ~eekly and removed~
~ total OI 76.,1 % e~ the emerged plant~ i~L the untreated 20 contrs~l were diseased,. The protectlve e:~fe~t o~ th~
treatment wa~ calculated as Iol:Low~:

~ttack i~ tre~ted . :L00 100 ~ e~ect ~ttack in ~treated The compound~ accordi~lg to the i~vention were us2d a~ 20 % ~trength ~orm~at~ on~, ~ompou~d according to t:he i~entlo~ ~o, ~ e~ect ~7 $ 4 g7 6 8~

14 aompari~on a~erLts beta~ 33iphen~1 4-~lo~y)-~
alpha~(l, l~di~ethyïe~hyl~
1, 2 9 4-triazol-1 et~anol 51 1 5 1- ( 4~Chlorophe~o~ dimethyl-1-(1,2~4-triazol-1wyl)~ 2-b~tarLorle ~7 i

Claims (172)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A 1,2,4-triazol-1-yl propionitrile of the general formula I

in which R represents an aryl radical which is unsubstituted or substituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)alkyl groups, (C1-C4)alkoxy groups, (C1-C4) alkylthio groups, trifluoromethyl groups and nitro groups, and R1 represents a (C1-C10)alkyl radical, (C3-C8)alkenyl radical, (C3-C8)alkynyl radical, or a phenyl-alkyl radical which is unsubstituted or sub-stituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)alkyl groups, (C1-C4)alkoxy groups, (C1-C4)alkylthio groups, trifluoromethyl groups and nitro groups.

2. A compound as claimed in claim 1, in which R represents a phenyl radical which is unsubstituted or substituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)alkyl groups, (C1-C4)alkoxy groups, (C1-C4)alkylthio groups, trifluoromethyl groups and nitro groups, and R1 represents a (C1-C10)alkyl radical, (C3-C8)alkenyl radical, or a benzyl radical which is unsubtituted or substituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)alkyl groups, (C1-C4)alkoxy groups, (C1-C4 )alkylthio groups, trifluoromethyl groups and nitro groups.

3. A compound as claimed in claim 2, wherein R represents a phenyl group which is unsubstituted or substituted by one or more alkyl groups and/or halogen atoms, and R1 represents a (C1-C10)alkyl group or an allyl group.

4. A compound as claimed in claim 3, wherein .
R represents a phenyl, 2-chlorophenyl, 3-chloro-phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 4-bromophenyl, 2-fluorophenyl, 4-fluorophenyl or 2-methylphenyl group and represents an ethyl, allyl, propyl, isopropyl, butyl or hexyl group.

5. A compound as claimed in claim 4, wherein R represents a phenyl, 4-chlorophenyl or 2-methyl-phenyl group and R1 represents a propyl, isopropyl or butyl group.

6. An acid addition salt of a compound as claimed in claim 1.

7. An acid addition salt as claimed in claim 6, which is a hydronitrate salt.

8. 2-Isopropoxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propionitrile hydronitrate.

9. 2-Isopropoxy-2-phenyl-3-(1,2,4 triazol-l-yl)-propionitrile.

10. 2-Hexyloxy-2-(2-methylphenyl)-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

11. 2-Butoxy-2-(2-methylphenyl)-3-(1,2,4-triazol-1-yl)-propionitrile.

12. 2-Butoxy-2-(2-methylphenyl)-3-(1,2,4-triazol l-yl)-propionitrile hydronitrate.

13. 2-Hexyloxy-2-(2-methylphenyl)-3-(1,2,4-triazol-l-yl)-propionitrile.

14. 2-Butoxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propionitrile hydronitrate.

15. 2-Butoxy-2-(2-chlorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

16. 2-Ethoxy-2-phenyl-3-(1,2,4-triazol-1-yl)-propionitrile hydronitrate.

17. 2-Phenyl-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

18. 2-(3-Chlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

19. 2-Butoxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile.

20. 2-Phenyl-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

21. 2-Ethoxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile.

22. 2-Hexyloxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

23. 2-Allyloxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

24. 2-Butoxy-2-(4-chlorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

25. 2-Allyloxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile.

26. 2-Methoxy-2-phenyl-3-(1,2,4-triazol-l-yl)-propionitrile.

27. 2-Hexyloxy-2-phenyl-3-(1,2,4-triazol-l-yl) propionitrile.

28. 2-(2-Chlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

29. 2-(2-Chlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

30. 2-(4-Chlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

31. 2-(4-Chlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

32. 2-(4-Chlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

33. 2-Butoxy-2-(4-chlorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrile.

34. 2-(2-Methylphenyl)-2-octyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

35. 2-Decyloxy-2-(2-methylphenyl)-3-(1y2,4-triazol l-yl)-propionitrile hydronitrate.

36. 2-(2-Methylphenyl)-2-octyloxy-3-(1,2,4-triazol-l-yl)-propionitrile.

37. 2-Butoxy-2-(2-chlorophenyl)-3-i1,2,4-triazol-l-yl)-propionitrile.

38. 2-(2-Chlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl) propionitrile.

39. 2-Butoxy-2-(2,4-dichlorophenyl)-3-(1,2 7 4 triazol-l-yl)-propionitrile hydronitrate.

40. 2-Butoxy-2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrile.

41. 2-Allyloxy 2-(2,4-dichlorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrlle.

42. 2-(3,4-Dichlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrat2.

43. 2-(3,4-Dichlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

44. 2-(3,4-Dichlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

45. 2-(3,4-Dichlorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile.

46. 2-(4-Fluorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

47. 2-(4-Fluorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl-propionitrile.

48. 2-Butoxy-2-(4-fluorophenyl)-3-(1,2,4-triazol l-yl)-propionitrile hydronitrate.

49. 2-Butoxy-2-(4-fluorophenyl)-3-(102,4-t.riazol-l-yl)-propionitrile.

50. 2-(2-Fluorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

51. 2-(2-Fluorophenyl)-2-propoxy-3-(1,2,4-triazol l-yl)-propionitrile.

52. 2-Butoxy-2-(2-fluorophenyl)-3-(1,2,4-triazol l-yl)-propionitrile hydronitrate.

53. 2-Butoxy-2-(2-fluorophenyl)-3-(1,2,4-triazol-l-yl)-propionitrile.

54. 2-(2-Fluorophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

55. 2-(2-Fluorophenyl)-2-hexyloxy 3-(1,2,4-triazol-l-yl)-propionitrile.

56. 2-(4-Bromophenyl)-2-propoxy-3-(1,2,4 triazol-l-yl)-propionitrile hydronitrate.

57. 2-(4-Bromophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

58. 2-(4-Bromophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

59. 2-(4-Bromophenyl)-2-hexyloxy-3-(1,2,4-triazol-l-yl)-propionitrile.

60. 2-(2,4-Dichlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

61. 2-(2,4-Dichlorophenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

62. 2-(2-Methylphenyl)-2-pentyl-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

63. 2-(2-Methylphenyl)-2-pentyl-3-(1,2,4-triazol-l-yl)-propionitrile.

64. 2-(4-Methylphenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

65. 2-Hexyloxy-2-(4-methylphenyl)-3-(1,2,4-triazol-l-yl)-propionitrile hydronitrate.

66. 2-(4-Methylphenyl)-2-propoxy-3-(1,2,4-triazol-l-yl)-propionitrile.

67. 2-Hexyloxy-2-(4-methylphenyl)-3-(1,2,4-triazol-l-yl)-propionitrile.

68. 2-Butoxy-2-(4-methylphenyl)-3-(1,2,4-triazol l-yl)-propionitrile.

69. A process for the preparation of a compound of the general formula I as claimed in claim 1, or an acid addition salt thereof, which comprises reacting a compound of the general formula II

in which R and Rl have the meanings given in claim 1 and Y represents a halogen atom or an alkylsulphonyloxy or arylsulphonyloxy radical which is optionally halogenated in the side chain with 1,2,4-triazole of the formula or an alkali metal derivative thereof if desired in the presence of a solvent and, optionally, in the presence of a base and, if desired, a compound of the general formula I

is converted into an acid addition salt thereof with an acid and/or an acid addition salt is converted into a corresponding free compound of the general formula I.

70. A process as claimed in claim 69 which is carried out at a temperature in the range of from 100 to 200°C.

71. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 1 and acid addition salts thereof.

72. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 2, 3 or 4 and acid addition salts thereof.

73. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 5, 6 or 7 and acid addition salts thereof.

74. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 8, 9 or 10 and acid addition salts thereof.

75. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 11, 12 or 13 and acid addi-tion salts thereof.

76. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 14, 15 or 16 and acid addi-tion salts thereof.

77. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 17, 18 or 19 and acid addi-tion salts thereof.

78. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 20, 21 or 22 and acid addi-tion salts thereof.

79. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 23, 24 or 25 and acid addi-tion salts thereof.

80. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 26, 27 or 28 and acid addi-tion salts thereof.

81. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 29, 30 or 31 and acid addi-tion salts thereof.

82. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plan-t and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 32, 33 or 34 and acid addi-tion salts thereof.

83. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 35, 36 or 37 and acid addi-tion salts thereof.

84. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 38, 39 or 40 and acid addi-tion salts thereof.

85. A method as claimed in claim 71, wherein a compound selected from compounds of the general formula I
and salts thereof is used for the treatment in an amount in the range of from 0.05 to 5 kg per hectare.

86. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 1 and acid addition salts thereof.

87. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 2, 3 or 4 and acid addition salts thereof.

88. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 5, 6 or 7 and acid addition salts thereof.

89. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 8, 9 or 10 and acid addition salts thereof.

90. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 1l, 12 or 13 and acid addition salts thereof.

91. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 14, 15 or 16 and acid addition salts thereof.

92. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 17, 18 or 19 and acid addition salts thereof.

93. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is treated with a compound selected from compounds of claim 20, 21 or 22 and acid addition salts thereof.

94. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 23, 24 or 25 and acid addition salts thereof.

95. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 26, 27 or 28 and acid addition salts thereof.

96. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 29, 30 or 31 and acid addition salts thereof.

97. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 32, 33 or 34 and acid addition salts thereof.

98. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 35, 36 or 37 and acid addition salts thereof.

99. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 38, 39 or 40 and acid addition salts thereof.

100. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 41, 42 or 43 and acid addition salts thereof.

101. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 44, 45 or 46 and acid addition salts thereof.

102. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-with a compound selected from compounds of claim 47, 48 or 49 and acid addition salts thereof.

103. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 50, 51 or 52 and acid addition salts thereof.

104. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 53, 54 or 55 and acid addition salts thereof.

105. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 56, 57 or 58 and acid addition salts thereof.

106. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 59, 60 or 61 and acid addition salts thereof.

107. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 62, 63 or 64 and acid addition salts thereof.

108. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 65, 66 or 67 and acid addition salts thereof.

109. A method of protecting a crop area against weeds and/or phytopathogenic fungi and/or of regulating the growth of plants in the area, wherein the crop area is trea-ted with a compound selected from compounds of claim 68 and acid addition salts thereof.

110. A method as claimed in claim 86, wherein a compound selected from compounds of the general formula I and salts thereof is used for the treatment in an amount in the range of from 0.05 to 5 kg per hectare.

111. A method as claimed in claim 86, wherein the crop is a plantation crop.

112. A method as claimed in claim 86, wherein the crop is a cereal, cotton, sugar or soya bean crop.

113. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 1 and an acid addition salt thereof.

114. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 2, 3 or 4 and acid addition salts thereof.

115. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 5, 6 or 7 and acid addition salts thereof.

116. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 8, 9 or 10 and acid addition salts thereof.

117. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 11, 12 or 13 and acid addition salts thereof.

118. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 14, 15 or 16 and acid addition salts thereof.

119. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 17, 18 or 19 and acid addition salts thereof.

120. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 20, 21 or 22 and acid addition salts thereof.

121. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 23, 24 or 25 and acid addition salts thereof.

122. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 26, 27 or 28 and acid addition salts thereof.

123. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 29, 30 or 31 and acid addition salts thereof.

124. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 32, 33 or 34 and acid addition salts thereof.

125. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 35, 36 or 37 and acid addition salts thereof.

126. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 38, 39 or 40 and acid addition salts thereof.

127. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 41, 42 or 43 and acid addition salts thereof.

128. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 44, 45 or 46 and acid addition salts thereof.

129. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 47, 48 or 49 and acid addition salts thereof.

130. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 50, 51 or 52 and acid addition salts thereof.

131. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 53, 54 or 55 and acid addition salts thereof.

132. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 56, 57 or 58 and acid addition salts thereof.

133. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 59, 60 or 61 and acid addition salts thereof.

134. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 62, 63 or 64 and acid addition salts thereof.

135. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 65, 66 or 67 and acid addition salts thereof.

136. A method of dressing seeds, wherein the seeds are treated with a compound selected from compounds of claim 68 and acid addition salts thereof.

137. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 1 and acid addition salts thereof.

138. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 2, 3 or 4 and acid addition salts thereof.

139. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 5, 6 or 7 and acid addition salts thereof.

140. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 8, 9 or 10 and acid addi-tion salts thereof.

141. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 11, 12 or 13 and acid addi-tion salts thereof.

142. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 14, 15 or 16 and acid addi-tion salts thereof.

143. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 17, 18 or 19 and acid addi-tion salts thereof.

144. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 20, 21 or 22 and acid addi-tion salts thereof.

145. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 23, 24 or 25 and acid addi-tion salts thereof.

146. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 26, 27 or 28 and acid addi-tion salts thereof.

147. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 29, 30 or 31 and acid addi-tion salts thereof.

148. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 32, 33 or 34 and acid addi-tion salts thereof.

149. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 35, 36 or 37 and acid addi-tion salts thereof.

150. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 38, 39 or 40 and acid addi-tion salts thereof.

151. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 41, 42 or 43 and acid addi-tion salts thereof.

152. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 44, 45 or 46 and acid addi-tion salts thereof.

153. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 47, 48 or 49 and acid addi-tion salts thereof.

154. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 50, 51 or 52 and acid addi-tion salts thereof.

155. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 53, 54 or 55 and acid addi-tion salts thereof.

156. A method of protecting a substate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 56, 57 or 58 and acid addi-tion salts thereof.

157. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 59, 60 or 61 and acid addi-tion salts thereof.

158. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 62, 63 or 64 and acid addi-tion salts thereof.

159. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 65, 66 or 67 and acid addi-tion salts thereof.

160. A method of protecting a substrate against bacteria, wherein the substrate is treated with a compound selected from compounds of claim 68 and acid addition salts thereof.

161. A method as claimed in claim 137, wherein the substrate is a living plant or an area in the vicinity of the living plant.

162. A method as claimed in claim 137, wherein the substrate is an inanimate object.

163. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 41, 42 or 43 and acid addition salts thereof.

164. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 44, 45 or 46 and acid addition salts thereof.

165. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 47, 48 or 49 and acid addition salts thereof.

166. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 50, 51 or 52 and acid addition salts thereof.

167. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 53, 54 or 55 and acid addition salts thereof.

168. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 56, 57 or 58 and acid addi-tion salts thereof.

169. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 59, 60 or 61 and acid addition salts thereof.

170. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 62, 63 or 64 and acid addi-tion salts thereof.

171. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 65, 66 or 67 and acid addition salts thereof.

172. A method of protecting a living plant against weeds and/or phytopathogenic fungi and/or of regulating its growth, wherein the living plant and/or the area in the vicinity of the living plant is/are treated with a compound selected from compounds of claim 68 and acid addition salts thereof.