5- (2-Arylacetamido) isothiazole compounds having pesticidal and fungicidal action have been described in various documents of the prior art, for example in DE-A 19846008, WO 95/31448, WO 97/18198, WO 98/02424, WO 01/55144, WO 01/55145, WO 01/90105, WO 02/059118, WO 02/059119 and WO 02/059120.

In principle, there is a constant demand for novel active compounds which allow the control of harmful fungi and/or animal pests, in order to widen the activity spectrum or to prevent a possible development of resistance against known active compounds.

Novel active compounds should kill the harmful fungi and/or the animal pests at application rates which are as low as possible and reduce or, even better, prevent their reestablishment. Moreover, the active compounds should be well tolerated by useful plants, i. e. they should cause little, if any, damage to the useful plants.

It is an object of the present invention to provide active compounds which allow the control of harmful fungi and/or animal pests. In particular, this object should be achieved at low application rates, with good compatibility with useful plants.

We have found that this object is, surprisingly, achieved by the 5- (2-arylacetamido)- isothiazole compounds of the formula I described below and by their agriculturally acceptable salts.

Accordingly, the present invention relates to 5- (2-arylacetamido) isothiazole compounds of the formula I in which X is oxygen or sulfur ; R'is hydrogen, Cy-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy ;

R2 is a group-C (R2a) =C (R2b) (R2C) or a group-C=C-R2d in which R2a, R2b, R2C and R2d independently of one another are H, C1-C4-alkyl which may carry a hydroxyl group or a Ci-C4-alkoxy group, C1-C4-haloalkyl or C3-C6-cycloalkyl ; R3 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkylcarbonyl, C1-C4-alkoxy-C1-C4-alkyl or a group C02-R3a in which R3a is C1-C6- alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-cycloalkyl, phenyl or benzyl, where the phenyl ring of the two last-mentioned groups may have 1,2 or 3 substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy ; R4 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl ; R5 is hydrogen, halogen, C1-C4-alkyl or C1-C4-haloalkyl ; R6 is hydrogen, halogen, nitro, amino, cyano,-COOH,-CHO, C1-C6-alkyl, C3-C6- cycloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, (C1-C4-alkyl) amino, di- (Ci-C4-alkyl)- amino, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, Ci-C6-alkylcarbonyl, C1-C4-alkoxycarbonyl, where the 12 last-mentioned groups may have 1,2 or 3 substituents selected from the group consisting of halogen and C1-C4-alkoxy, is a group of the formula R7O-N=C(R8)- in which R7 is Ct-C6-alkyl or phenyl-Cl- C4-alkyl, where the alkyl moiety of the two last-mentioned groups may have 1,2 or 3 substituents selected from the group consisting of Ct-C4-alkoxy and halogen and the phenyl moiety in phenyl-C1-C4-alkyl may have 1,2 or 3 substituents selected from the group consisting of Ci-C4-alkoxy, hydroxyl and halogen, and Ra is hydrogen or C-C6-alkyl which may be substituted by halogen or C1-C4-alkoxy, is phenyl, benzyl, phenylthio, phenoxy, benzyloxy or benzylthio, where the phenyl ring of the 6 last-mentioned groups may have 1 or 2 substituents selected from the group consisting of halogen, nitro, cyano, hydroxyl, C1-C4-alkyl, C1-C4- haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1- C4-alkylsulfonyl and benzyloxy ; and n is 1,2 or 3; and the agriculturally acceptable salts of compounds of the formule 1.

The present invention also provides the use of the compounds of the formula I and their agriculturally acceptable salts for controlling plant-damaging microorganisms, in particular phytopathogenic fungi (= harmful fungi), and a method for controlling plant- damaging microorganisms which comprises treating the plant-damaging micro- organisms or the materials, plants, the soil or seeds to be protected against attack by plant-damaging microorganisms with an effective amount of a compound of the formula I and/or an agriculturally acceptable salt of 1.

The present invention also provides the use of the compounds of the formula I and their agriculturally acceptable salts as pesticides, i. e. for controlling plant-damaging animal organisms, and a method for controlling plant-damaging animal organisms which comprises treating the plant-damaging animal organisms or the materials, plants, the soil or seeds to be protected against attack by plant-damaging animal organisms with an effective amount of a compound of the formula I and/or with an agriculturally acceptable salt of 1.

The present invention furthermore provides an agricultural composition which comprises at least one compound of the formula I and/or an agriculturally acceptable salt of I and at least one agriculturally acceptable carrier.

The present invention furthermore provides a composition for controlling harmful fungi, which composition comprises at least one compound of the formula I and/or an agriculturally acceptable salt thereof and at least one liquid or solid carrier.

Depending on the substitution pattern, the compounds of the formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. The present invention provides both the pure enantiomers or diastereomers and their mixtures. The present invention also provides tautomers of compounds of the formula 1.

Suitable agriculturally useful salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no negative effect on the fungicidal action of the compounds 1. Thus, suitable cations are in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions,

sulfonium ions, preferably tri (Ci-C4-alkyl) sulfonium, and sulfoxonium ions, preferably tri (Ci-C4-alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen- sulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

They can be formed by reacting I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

In the definitions of the variables given in the formulae above, collective terms are used which are generally representative for the respective substituents. The term Cn-Cm denotes the number of carbon atoms possible in each case in the respective substituent or substituent moiety: halogen : fluorine, chlorine, bromine and iodine; alkyl and all alkyl moieties in alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl- amino, dialkylamino and alkylcarbonyl : saturated straight-chain or branched hydrocarbon radicals having 1 to 4 or 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethyl- butyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethyl- propyl, 1,2, 2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl ; haloalkyl and all haloalkyl moieties in haloalkoxy : straight-chain or branched alkyl groups having 1 to 4 or 1 to 6 carbon atoms (as mentioned above), where in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example C1-C2-haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloro- <BR> <BR> <BR> fluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2, 2-trichloroethyl, pentafluoro- ethyl, 2,2, 3,3, 3-pentafluoropropyl, heptafluoropropyl and 1,1, 1-trifluoroprop-2-yl ; alkenyl : monounsaturated straight-chain or branched hydrocarbon radicals having 2 to 4 or 2 to 6 carbon atoms and a double bond in any position, for example C2-C6-alkenyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl,

3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2- propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl- 1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2- propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl- 2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1- pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2- pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4- pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl- 2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3- butenyl, 2, 2-dimethyl-3-butenyl, 2, 3-dimethyl-1-butenyl, 2, 3-dimethyl-2-butenyl, 2, 3-dimethyl-3-butenyl, 3, 3-dimethyl-1-butenyl, 3, 3-dimethyl-2-butenyl, 1-ethyl-1- butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2- methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl ; alkynyl : straight-chain or branched hydrocarbon groups having 2 to 4 or 2 to 6 carbon atoms and a triple bond in any position, for example C2-C6-alkynyl, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyi, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3- butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl-2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, 3, 3-dimethyl-1- <BR> <BR> <BR> butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2- propynyl ; cycloalkyl : monocyclic saturated hydrocarbon groups having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl ; C-C4-alkoxy : an alkyl group having 1 to 4 carbon atoms which is attached via an oxygen: for example methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methyl- propoxy, 2-methylpropoxy or 1, 1-dimethylethoxy ; C1-C6-alkoxy : C,-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethyl- propoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methyl-

pentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1, 2-trimethylpropoxy, 1,2, 2-trimethylpropoxy, 1-ethyl-1- methylpropoxy or 1-ethyl-2-methylpropoxy ; C,-C4-haloalkoxy : a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, preferably by fluorine, i. e. , for example OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2- fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2,2, 2-trichloro- ethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2, 2-difluoropropoxy, 2, 3-difluoro- propoxy, 2-chloropropoxy, 3-chloropropoxy, 2, 3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3, 3-trifluoropropoxy, 3,3, 3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1- (CH2F)-2-fluoroethoxy, 1- (CH2CI)-2-chloroethoxy, 1- (CH2Br)-2-bromo- ethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy ; Ci-C6-haloalkoxy : C,-C4-haloalkoxy as mentioned above, and also, for example ; 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoro- pentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodeca- fluorohexoxy ; C1-C2-fluoroalkyl : Ci-C2-alkyl which carries 1,2, 3,4 or 5 fluorine atoms, for example difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2,2, 2-trifluoroethyl, 1,1, 2, 2-tetrafluoroethyl and pentafluoroethyl ; Ct-C2-fluoroalkoxy : Ci-C2-alkoxy which carries 1,2, 3,4 or 5 fluorine atoms, for example difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2, 2-difluoroethoxy, 2,2, 2- trifluoroethoxy, 1,1, 2, 2-tetrafluoroethoxy and pentafluoroethoxy ; alkylthio : straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as mentioned above) which are attached to the skeleton via a sulfur atom (-S-); alkoxyalkyl : an alkoxy group having 1 to 4 carbon atoms (as mentioned above) which is attached to the skeleton via a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as mentioned above); alkylcarbonyl : a straight-chain or branched alkyl group having 1 to 6 carbon atoms (as mentioned above) which is attached to the skeleton via a carbonyl group (-CO-);

alkylsulfinyl : a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as mentioned above) which is attached to the skeleton via a sulfinyl group (-SO-); alkylsulfonyl : a straight-chain or branched alkyl group having 1 to 4 carbon atoms (as mentioned above) which is attached to the skeleton via a sulfonyl group (-SO2-).

With respect to the activity of the compounds according to the invention, the variables n, X, R1, R2, R2a, R2b, R, R, R3, R4, R5 and R6 independently of one another and preferably in combination are preferably as defined below.

Preferably, n in formula) is 1 or 2. If n is 2, one substituent R5 is preferabiy located in the 3-position and the other substituent in the 4-position relative to the group CR4R5.

X is preferably oxygen.

R'in formula I is preferably Ci-C4-alkyl and very particularly preferably methyl.

R2a, R2b, R2C and R2d are preferably selected from the group consisting of hydrogen and Ci-C4-alkyl, especially methyl. In particular, R2a and R2b are hydrogen.

Particularly preferably, R2 in formula I is vinyl, cis-or trans-propen-1-yl, isopropenyl, ethynyl or propyn-1-yl, and very particularly preferably ethynyl.

R3 in formula I is preferably hydrogen, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl or a group COOR3a, where R3a is as defined above and is in particular Ci-C4-alkyl or benzyl. In particular, R3 is hydrogen.

Preferably at least one of the radicals R4 and R5 in formula I is hydrogen. In this case, the other radical R4 or R5 is preferably Ci-C4-alkyl, especially methyl. In particular, both R4 and R5 are hydrogen.

In a preferred embodiment of the present invention, at least one substituent R6 in formula I is selected from the group consisting of C1-C4-alkyl, C1-C4-alkoxy, Ci-C2- fluoroalkyl, C1-C2-fluoroalkoxy, C1-C4-alkylcarbonyl, Ci-C4-alkoxycarbonyl and halogen, for example from the group consisting of tert-butyl, methoxy, trifluoromethyl, trifluoromethoxy, methoxycarbonyl, acetyl, chlorine, fluorine and bromine.

In a further preferred embodiment of the present invention, at least one substituent R5 in formula I is selected from the group consisting of phenyl, benzyl, phenylthio, phenoxy, benzyloxy and benzylthio, and especially selected from the group consisting

of phenyloxy and benzyloxy. In this embodiment, the following radicals are preferred as substituent on the phenyl ring in phenyl, benzyl, phenylthio, phenoxy, benzyloxy and benzylthio : halogen, nitro, cyano, C-C4-alkyl, C1-C4-haloalkyl, C,-C4-alkoxy, Ci-C4- haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl and benzyloxy ; in particular halogen, nitro, cyano, C,-C4-alkyl, C1-C2-fluoroalkyl, Ci-C4-alkoxy and Cl-C4- alkylsulfonyl and especially halogen, CN, NO2, Ci-C4-alkyl, methoxy, methylsulfonyl and trifluoromethyl.

In principle, the substituents R6 can be located in any position on the phenyl ring. With a view to the activity of the compounds I according to the invention, a substituent R6 is preferably located in the para-position to the group CR4R5, in particular if the substituent in question is a radical R6 which is selected from the group consisting of unsubstituted or substituted phenyl, benzyl, phenylthio, phenoxy and benzyloxy.

With a view to the activity of the compounds I according to the invention, one substituent R6 is very particularly preferably phenoxy which may be substituted in the manner mentioned above. Below, these compounds are referred to as compounds). A.

Among these, preference is given to those compounds in which the phenyl ring in phenoxy has at least one, for example 1 or 2, of the abovementioned substituents and in particular exactly one of the abovementioned substituents in the para-position to the phenoxy oxygen. The substituent in the para-position is in particular selected from the group consisting of halogen, nitro, cyano, C1-C4-alkyl, C1-C2-fluoroalkyl, C1-C4-alkoxy and C1-C4-alkylsulfonyl and especially from the group consisting of halogen, CN, N02, Ci-C4-alkyl, methoxy, methylsulfonyl and trifluoromethyl.

Compounds of the formula I in which at least one substituent R6 is unsubstituted or substituted phenyl are referred to below as compounds). B; these compounds are likewise particularly preferred.

Compounds of the formula I in which at least one substituent R6 is unsubstituted or substituted benzyl are referred to below as compounds I. C; these compounds are likewise particularly preferred.

Compounds of the formula I in which at least one substituent R6 is unsubstituted or substituted benzyloxy are referred to below as compounds). D; these compounds are likewise particularly preferred.

Among the compounds I. A-I. D, preference is given to 5- (2-arylacetamido) isothiazole compounds of the formulae I. A1, I. B1, I. C1, I. D1, I. D2 and I. D3

(I. D3) in which the substituents are as defined below : R'is C,-C4-alkyl ; R2 is vinyl, cis-propen-1-yl, trans-propen-1-yl, ethynyl, propyn-1-yl, in particular ethinyl ; R3 is hydrogen, C1-C4-alkyl or C1-C4-alkoxy-C1-C4-alkyl ;

R4 is hydrogen or C1-C4-alkyl, and in which Ra, Rb independently of one another are selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl and benzyloxy ; particularly preferably selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-C4-alkyl, C1-C2-fluoroalkyl, C1-C4-alkoxy and C1-C4- alkylsulfonyl and especially selected from the group consisting of hydrogen, halogen, CN, NO2, C1-C4-alkyl, methoxy, methylsulfonyl and trifluoromethyl. Rb is preferably hydrogen.

Examples of compounds which are represented bythe formulae I. A1, I. B1, I. C1, I. D1, I. D2 and I. D3 are the individual compounds compiled in Tables 1 to 60 below.

Table A: No. R3 R4 Ra R A-1 H H H H A-2 H H F H A-3 H H Cl H A-4 H H Br H A-5 H H CF3 H A-6 H H NO2 H A-7 H H CN H A-8 H H SO2CH3 H A-9 H H OCH3 H A-10 H H OCH3 OCH2C6H5 A-11 H H OCH3 OCH3 A-12 H H CH3 H A-12 H H CH3 H A-13 H H C2H5 H A-14 H H CH (CH2) 3 H A-15 H H F F A-16 H H F Cl A-17 H CH3 H H A-18 H CH3 F H A-19 H CH3 Cl H A-20 H CH3 Br H A-21 H CH3 CF3 H A-22 H CH3 N02 H A-23 H CH3 CN H A-24 H CH3 S02CH3 H No. R3 R4 Ra R A-25 H CH3 OCH3 H A-26 H CH3 OCH3 OCH2C6H5 A-27 H CH3 OCH3 OCH3 A-28 H CH3 CH3 H A-29 H CH3 C2H5 H A-30 H CH3 CH (CH2) 3 H A-31 H CH3 F F A-32 H CH3 F Cl A-33 CH3 H H H A-34 CH3 H F H A-35 CH3 H Cl H A-36 CH3 H Br H A-37 CH3 H CF3 H A-38 CH3 H NO2 H A-39 CH3 H CN H A-40 CH3 H SO2CH3 H A-41 CH3 H OCH3 H A-42 CH3 H OCH3 OCH2C6H5 A-43 CH3 H OCH3 OCH3 A-44 CH3 H CH3 H A-45 CH3 H C2H5 H A-46 CH3 H CH (CH2) 3 H A-47 CH3 H F F A-48 CH3 H F Cl A-49 CH3 CH3 H H A-50 CH3 CH3 F H A-51 CH3 CH3 Cl H A-52 CH3 CH3 Br H A-53 CH3 CH3 CF3 H A-54 CH3 CH3 N02 H A-55 CH3 CH3 CN H A-56 CH3 CH3 SO2CH3 H A-57 CH3 CH3 OCH3 H A-58 CH3 CH3 OCH3 OCH2C6H5 A-59 CH3 CH3 OCH3 OCH3 A-60 CH3 CH3 CH3 H A-61 CH3 CH3 C2H5 H A-62 CH3 CH3 CH (CH2) 3 H No. R3 R4 Ra R6 A-63 CH3 CH3 F F A-64 CH3 CH3 F Cl A-65 CH20CH3 H H H A-66 CH20CH3 H F H A-67 CH2OCH3 H Cl H A-68 CH20CH3 H Br H A-69 CH20CH3 H CF3 H A-70 CH2OCH3 H NO2 H A-71 CH20CH3 H CN H A-72 CH20CH3 H S02CH3 H A-73 CH20CH3 H OCH3 H A-74 CH20CH3 H OCH3 OCH2C6H5 A-75 CH20CH3 H OCH3 OCH3 A-76 CH20CH3 H CH3 H A-77 CH20CH3 H C2H5 H A-78 CH20CH3 H CH (CH2) 3 H A-79 CH20CH3 H F F A-80 CH2OCH3 H F Cl A-81 CH20CH3 H H H A-82 CH2OCH3 CH3 F H A-83 CH20CH3 CH3 Cl H A-84 CH2OCH3 CH3 Br H A-85 CH2OCH3 CH3 CF3 H A-86 CH2OCH3 CH3 NO2 H A-87 CH2OCH3 CH3 CN H A-88 CH20CH3 CH3 S02CH3 H A-89 CH20CH3 CH3 OCH3 H A-90 CH20CH3 CH3 OCH3 OCH2C6H5 A-91 CH20CH3 CH3 OCH3 OCH3 A-92 CH20CH3 CH3 CH3 H A-93 CH20CH3 CH3 C2H5 H A-94 CH20CH3 CH3 CH (CH2) 3 H A-95 CH20CH3 CH3 F F A-96 CH20CH3 CH3 F Table 1 : Compounds of the formula). A1, in which

Rt is methyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 2: Compounds of the formula I. A1 in which Rt is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 3: Compounds of the formula). A1 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 4: Compounds of the formula I. A1 in which R'is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 5: Compounds of the formula I. A1 in which R'is methyl, Rz is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 6: Compounds of the formula I. A1 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 7: Compounds of the formula I. A1 in which R'is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 8:

Compounds of the formula). A1 in which R'is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 9: Compounds of the formula I.A1 in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 10: Compounds of the formula I. A1 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 11 : Compounds of the formula I. B1 in which R'is methyl, R2 is ethynyl, R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 12 : Compounds of the formula I. B1 in which R'is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 13 : Compounds of the formula I. B1 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 14 : Compounds of the formula I. B1 in which R1 is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 15 : Compounds of the formula I. B1 in which R'is methyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 16 : Compounds of the formula I. B1 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 17 : Compounds of the formula I. B1 in which Rt is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 18 : Compounds of the formula I. B1 in which R'is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 19 : Compounds of the formula l. B1 in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 20: Compounds of the formula I. B1 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 21: Compounds of the formula I.C1 in which

R1 is methyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 22: Compounds of the formula I. C1 in which R'is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 23: Compounds of the formula I. C1 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 24: Compounds of the formula I. C1 in which R'is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 25: Compounds of the formula I.C1 in which R'is methyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 26: Compounds of the formula I. C1 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 27: Compounds of the formula I. C1 in which R'is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 28:

Compounds of the formula I. C1 in which R1 is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 29: Compounds of the formula I. C1 in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 30: Compounds of the formula I. C1 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 31: Compounds of the formula). D1 in which R'is methyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 32: Compounds of the formula I.D1 in which R'is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 33: Compounds of the formula I. D1 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 34: Compounds of the formula). D1 in which R'is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 35: Compounds of the formula). D1 in which R'is methyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 36: Compounds of the formula). D1 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 37: Compounds of the formula). D1 in which R'is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 38: Compounds of the formula I. D1 in which R'is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 39: Compounds of the formula I. D1 in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 40: Compounds of the formula). D1 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 41: Compounds of the formula l. D2 in which

R'is methyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 42: Compounds of the formula l. D2 in which R'is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 43: Compounds of the formula l. D2 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 44: Compounds of the formula I. D2 in which R'is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 45: Compounds of the formula l. D2 in which R'is methyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 46: Compounds of the formula I. D2 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 47: Compounds of the formula I. D2 in which R'is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 48:

Compounds of the formula I. D2 in which R1 is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond. in each case to one row of Table A.

Table 49: Compounds of the formula I. D2 in which R1 is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 50: Compounds of the formula I. D2 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 51 : Compounds of the formula I. D3 in which R'is methyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 52: Compounds of the formula I. D3 in which R1 is methyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 53: Compounds of the formula I. D3 in which R'is methyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 54: Compounds of the formula I. D3 in which R'is methyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 55: Compounds of the formula I. D3 in which R'is methyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 56: Compounds of the formula l. D3 in which R'is ethyl, R2 is ethynyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 57: Compounds of the formula I. D3 in which R1 is ethyl, R2 is propyn-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 58: Compounds of the formula l. D3 in which R'is ethyl, R2 is vinyl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 59: Compounds of the formula I. D3 in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Table 60: Compounds of the formula I. D3 in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4, Ra and Rb for each individual compound correspond in each case to one row of Table A.

Particular preference is also given to 5- (2-arylacetamido) isothiazole compounds of the formula l. E

in which the substituents are as defined below : R1 is C1-C4-alkyl ; R2 is vinyl, cis-propen-1-yl, trans-propen-1-yl, ethynyl, propyn-1-yl ; R3 is hydrogen, C1-C4-alkyl or C1-C4-alkyl ; R4 is hydrogen or C1-C4-alkyl, R6 is in each case independently of the other radicals R6 selected from the group consisting of halogen, C1-C4-alkyl, C1-C2-fluoroalkyl, C1-C2-fluoroalkoxy, Ci-C4- alkoxy, C1-C4-alkylcarbonyl and C1-C4-alkoxycarbonyl ; and in which n is 1 or 2.

Examples of compounds). E are the individual compounds in Tables 61 to 70 below.

Table B: No. R3 R4 (R6)n B-1 H H 2-F B-2 H H 3-F B-3 H H 4-F B-4 H H 2-Cl B-5 H H 3-CI B-6 H H 4-CI B-7 H H 4-CN B-8 H H 4-NO2 B-9 H H 4-CH3 B-10 H H 4-C2H5 B-11 H H 4-CH (CH3) 2 B-12 H H 4-C (CH3) 3 B-13 H H 4-CH (CH3) (C2H5) B-14 H H 4-CH2CH(CH3) 2 B-15 H H 4-CF3 B-16 H H 4-OCH3 B-17 H H 4-OCF3 B-18 H H 4-OC(CH3) 3 B-19 H H 3-OCH3, 4-OCH3; No. R3 R4 (R6)n B-20 H H 4-OCH2C6H5 B-21 H H 4-C (O) CH3 B-22 H H 4-C (O) OCH3 B-23 CH3 H 2-F B-24. CH3 H 3-F B-25 CH3 H 4-F B-26 CH3 H 2-Cl B-27 CH3 H 3-Cl B-28 CH3 H 4-Cl B-29 CH3 H 4-CN B-30 CH3 H 4-NO2 B-31 CH3 H 4-CH3 B-32 CH3 H 4-C2H5 B-33 CH3 H 4-CH (CH3) 2 B-34 CH3 H 4-C (CH3) 3 B-35 CH3 H 4-CH (CH3) (C2H5) B-36 CH3 H 4-CH2CH (CH3) 2 B-37 CH3 H 4-CF3 B-38 CH3 H 4-OCH3 B-39 CH3 H 4-OCF3 B-40 CH3 H 4-OC (CH3) 3 B-41 CH3 H 3-OCH3, 4-OCH3; B-42 CH3 H 4-OCH2C6H5 B-43 CH3 H 4-C (O) CH3 B-44 CH3 H 4-C (O) OCH3 B-45 H CH3 2-F B-46 H CH3 3-F B-47 H CH3 4-F B-48 H CH3 2-Cl B-49 H CH3 3-CI B-50 H CH3 4-CI B-51 H CH3 4-CN B-52 H CH3 4-NO2 B-53 H CH3 4-CH3 B-54 H CH3 4-C2H5 B-55 H CH3 4-CH (CH3) 2 B-56 H CH3 4-C (CH3) 3 B-57 H CH3 4-CH (CH3) (C2H5) No. R R4 (R6)n B-58 H CH3 4-CH2CH (CH3) 2 B-59 H CH3 4-CF3 B-60 H CH3 4-OCH3 B-61 H CH3 4-OCF3 B-62 H CH3 4-OC (CH3) 3 B-63 H CH3 3-OCH3, 4-OCH3; B-64 H CH3 4-OCH2C6H5 B-65 H CH3 4-C (O) CH3 B-66 H CH3 4-C (O) OCH3 B-67 CH3 CH3 2-F B-68 CH3 CH3 3-F B-69 CH3 CH3 4-F B-70 CH3 CH3 2-CI B-71 CH3 CH3 3-CI B-72 CH3 CH3 4-CI B-73 CH3 CH3 4-CN B-74 CH3 CH3 4-NO2 B-75 CH3 CH3 4-CH3 B-76 CH3 CH3 4-C2H5 B-77 CH3 CH3 4-CH (CH3) 2 B-78 CH3 CH3 4-C (CH3) 3 B-79 CH3 CH3 4-CH (CH3) (C2H5) B-80 CH3 CH3 4-CH2CH (CH3) 2 B-81 CH3 CH3 4-CF3 B-82 CH3 CH3 4-OCH3 B-83 CH3 CH3 4-OCF3 B-84 CH3 CH3 4-OC (CH3) 3 B-85 CH3 CH3 3-OCH3, 4-OCH3; B-86 CH3 CH3 4-OCH2C6H5 B-87 CH3 CH3 4-C (O) CH3 B-88 CH3 CH3 4-C (O) OCH3 B-89 CH20CH3 H 2-F B-90 CH20CH3 H 3-F B-91 CH20CH3 H 4-F B-92 CH2OCH3 H 2-Cl B-93 CH2OCH3 H 3-Cl B-94 CH2OCH3 H 4-Cl B-95 CH2OCH3 H 4-CN No. R3 R4 (R6)n B-96 CH2OCH3 H 4-NO2 B-97 CH20CH3 H 4-CH3 B-98 CH2OCH3 H 4-C2H5 B-99 CH20CH3 H 4-CH (CH3) 2 B-100 CH2OCH3 H 4-C(CH3) 3 B-101 CH20CH3 H 4-CH (CH3) (C2H5) B-102 CH2OCH3 H 4-CH2CH(CH3) 2 B-103 CH2OCH3 H 4-CF3 B-104 CH2OCH3 H 4-OCH3 B-105 CH2OCH3 H 4-OCF3 B-106 CH2OCH3 H 4-OC (CH3) 3 B-107 CH2OCH3 H 3-OCH3, 4-OCH3; B-108 CH2OCH3 H 4-OCH2C6H5 B-109 CH2OCH3 H 4-C(O) CH3 B-110 CH2OCH3 H 4-C (O) OCH3 B-111 CH2OCH3 CH3 2-F B-112 CH2OCH3 CH3 3-F B-113 CH2OCH3 CH3 4-F B-114 CH2OCH3 CH3 2-Cl B-115 CH2OCH3 CH3 3-Cl B-116 CH2OCH3 CH3 4-Cl B-117 CH2OCH3 CH3 4-CN B-118 CH2OCH3 CH3 4-NO2 B-119 CH2OCH3 CH3 4-CH3 B-120 CH2OCH3 CH3 4-C2H5 B-121 CH2OCH3 CH3 4-CH (CH3) 2 B-122 CH2OCH3 CH3 4-C (CH3) 3 B-123 CH2OCH3 CH3 4-CH (CH3) (C2H5) B-124 CH2OCH3 CH3 4-CH2CH (CH3) 2 B-125 CH2OCH3 CH3 4-CF3 B-126 CH20CH3 CH3 4-OCH3 B-127 CH2OCH3 CH3 4-OCF3 B-128 CH2OCH3 CH3 4-OC(CH3) 3 B-129 CH2OCH3 CH3 3-OCH3, 4-OCH3 ; B-130 CH2OCH3 CH3 4-OCH2C6H5 B-131 CH2OCH3 CH3 4-C(O)CH3 B-132 CH2OCH3 CH3 4-C(O)OCH3

Table 61: Compounds of the formula I. E in which R'is methyl, R2 is ethynyl and R3, R4 and (R6)n for each individual compound correspond in each case to one row of Table B.

Table 62: Compounds of the formula l. E in which R'is methyl, R2 is propyn-1-yl and R3, R4 and (R6)n for each individual compound correspond in each case to one row of Table B.

Table 63: Compounds of the formula I. E in which R'is methyl, R2 is trans-propen-1-yl and R3, R4 and (R6)n for each individual compound correspond in each case to one row of Table B.

Table 64: Compounds of the formula l. E in which R'is methyl, R2 is cis-propen-1-yl and R3, R4 and (R6) n for each individual compound in each case to one row of Table B.

Table 65: Compounds of the formula l. E in which R'is methyl, R2 is vinyl and R3, R4 and (R6) n for each individual compound in each case to one row of Table B.

Table 66: Compounds of the formula I. E in which R'is ethyl, R2 is ethynyl and R3, R4 and (R6)n for each individual compound correspond in each case to one row of Table B.

Table 67: Compounds of the formula I. E in which R'is ethyl, R2 is propyn-1-yl and R3, R4 and (R6) n for each individual compound

correspond in each case to one row of Table B.

Table 68: Compounds of the formula I. E in which R'is ethyl, R2 is trans-propen-1-yl and R3, R4 and (R6)n for each individual compound correspond in each case to one row of Table B.

Table 69: Compounds of the formula l. E in which R'is ethyl, R2 is cis-propen-1-yl and R3, R4 and (R6) n for each individual compound correspond in each case to one row of Table B.

Table 70: Compounds of the formula l. E in which R'is ethyl, R2 is vinyl and R3, R4 and (R6) n for each individual compound correspond in each case to one row of Table B.

The compounds of the formula I according to the invention can be prepared analogously to the methods described in the prior art cited at the outset. In general, in order to prepare compounds of the formula I where X = 0 and R3 = H, a 5-amino- isothiazole compound of the formula 11 is reacted in a process known per se with a carboxylic acid or a carboxylic acid derivative of the formula III in which L is a nucleophilically displaceable leaving group, for example OH, halogen, in particular chlorine, alkoxy and the like, as shown in Scheme 1. In the formulae 11 and IiI, R', R2, R4, R5, R6 and n are as defined above.

Scheme 1: This reaction is usually carried out at temperatures of from 0°C to 100°C, preferably from 0°C to 50°C, in an inert organic solvent. If L in formula III is a halogen atom, the

reaction is preferably carried out in the presence of a base. If L in formula III is OH, the reaction is preferably carried out in the presence of a coupling agent which activates the OH group.

Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons, such as toluene, o-, m-and p-xylene, halogenated hydrocarbons, such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, disopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles, such as acetonitrile and propionitrile, ketones, such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylformamide and dimethylacetamide and ethyl acetate. It is also possible to use mixtures of the solvents mentioned.

Suitable bases are, in general, alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and also alkali metal bicarbonates, such as sodium bicarboate, moreover organic bases, for example tertiary amines, such as trimethylamine, triethylamine, triisopropylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminopyridine, and also bicyclic amines. Particular preference is given to triethylamine, pyridine and 4-dimethylaminopyridine. The bases are generally employed in equimolar amounts; however, they can also be used in excess or, if appropriate, as solvent Suitable coupling agents are in particular carbodiimides, for example 1, 3-dicyclohexyl- carbodiimide, 1, 3-diisopropylcarbodiimide and 1- (3-dimethylaminopropyl)-3-ethylcarbo- diimide. The coupling agents are generally employed in equimolar amounts; however, they can also be used in excess, for example in an amount of up to 2 mol per mole of the compound Ill.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to use an excess of one of the reaction partners.

The reaction mixtures are worked up in a customary manner, for example by mixing with dilute acid, water or dilute base, separating the phases and, if appropriate, chromatographic purification of the crude products. Some of the intermediates and end products are obtained in the form of colorless or slightly brownish viscous oils which are free from volatile components or purified under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, the purification may also be carried out by recrystallization or digestion.

The compounds I where X = O and R3 = H obtained according to Scheme 1 can then be converted by alkylating or acylating processes known per se into compounds I where R3 has the meanings given above which are different from hydrogen. Processes suitable for this purpose are described, for example, in WO 02/059120 or by A. B. Smith et al., J. Am. Chem. Soc. , 1995 (117) p. 10777. To prepare compounds I where R3 ?"H, it is, of course, also possible, analogously to the method shown in Scheme 1, to react aminoisothiazoles which have a substituent R3 different from hydrogen at the amino nitrogen.

Compounds I where X = O may be converted by known methods to compounds of the formula I where X = S by treating with sulfurizing agents. Examples of suitable sulfurizing agents are organophosphorus sulfides such as Lawesson reagent, organotin sulfides or phosphorus (V) sulfides (see also J. March, Advanced Organic Synthesis, 2nd edition, Wiley Interscience 1985, p. 794 and literature cited there). The reaction may be carried out in a solvent or in substance. Suitable solvents are the abovementioned inert solvents and the like. The temperature required for the reaction is generally above room temperature and is in particular in the range from 50 to 200°C.

The aminoisothiazoles of the formula II required for preparing the compounds I can be prepared by processes known per se. A preferred route to aminoisothiazoles 11 is shown in Scheme 2.

Scheme 2: route a) e R'R'Hal-e RI 1 R cat S NH2 S NH2 [Pd] S NH2 N'SNH 2 (IV) (IIA) (IIB) Z-C (R2a) =C (R2b) (R2c) route b) [Pd] R2b V Ri roi X Rt, NH2 N NH2 S NH2 (IIB) (11) : {R2 = ethynyl}

In Scheme 2, R', R2a, R2b, R2 and R2d are as defined above. Re has the meanings given for R2b, R2C or R2d or is a trialkylsilyl radical, such as trimethylsilyl, triethylsilyl, dimethylbutylsilyl, etc. Hal is bromine or iodine. [Hal] is a brominating or iodinating agent. [Pd] is a homogeneous catalyst with palladium as active metal. Cat is a heterogeneous catalyst comprising a transition metal of group 8. Z is hydrogen, a trialkylstannyl radical in which alkyl has 1 to 6 carbon atoms, such as in tributylstannyl, a radical B (OR) 2 in which R is hydrogen or alkyl having 1 to 4 carbon atoms.

For this purpose, initially an isothiazole compound II I will be reacted with a brominating agent or an iodinating agent, for example N-bromosuccinimide or N-iodosuccinimide, if appropriate in an inert solvent, for example an alkane or a halogenated hydrocarbon or a mixture thereof. Processes to achieve this are known in principle, for example from WO 95/33418, and can be employed analogously to the preparation of the compound IV.

The resulting 5-amino-4-haloisothiazole IV can then be reacted according to route a) with an alkyne of the formula HC=C-Re in the presence of a palladium catalyst, giving the alkynylated isothiazole of the formula IIA. The palladium catalysts used are usually palladium salts or palladium compounds which are capable of forming Pd (0) complexes with triarylphosphines such as triphenylphosphine. If required, the use of copper (l) salts as cocatalysts may be recommended. Processes for this purpose are known in principle, for example from N. Harris et al., Synlett 1990 (10) p. 577, US 4705799, J. M.

Kehoe et al. Organic Lett. 2000 (2), p. 969, K. H. H. Fabian et al. Tetrahedron Lett. 2000 (41) p. 2855, and they can be employed analogously to the preparation of the compound IIA. The reaction of compound IV with the alkyne is preferably carried out in the presence of a base, preferably a tertiary organic amine, in particular a trialkylamine, such as triethylamine. The reaction is preferably carried out in a solvent or diluent, for example one of the solvents mentioned in connection with Scheme 1, in particular an ether.

If Reis a trialkylsilyl group, for example a trimethylsilyl group, this is subsequently removed by known processes. The removal of the trialkylsilyl group from the compound IIA can be carried out analogously to known processes for removing acetylenically attached trialkylsilyl groups, as described, for example, by C. J. Yu et al., J. Org. Chem. 1999, (64) p. 2070 or by D. Holmes et al., Chem. Eur. J. 1999 (5), p.

3399. To this end, the compound IIA is generally reacted with a fluoride source, for example a tetraalkylammonium fluoride, such as tetrabutylammonium fluoride, or an alkali metal fluoride, such as sodium fluoride or potassium fluoride, if appropriate in the presence of a complex ligand, such as a crown ether. The reaction is preferably carried

out in an organic solvent, for example in one of the solvents mentioned above, and in particular in an ether, such as tetrahydrofuran or dioxane.

If Re has the meaning given for R2b or R, the alkyne compound can also be subjected to a catalytic hydrogenation, giving the isothiazole compound IIB. Processes for the catalytic hydrogenation of alkynes are known to the person skilled in the art, for example from J. March, Advanced Organic Chemistry, 3rd edition, John Wiley & Sons 1985, pp. 691-700, and the literature cited therein. The catalysts used are usually supported palladium catalysts of the Lindlar type. Suitable carrier materials are generally barium sulfate or calcium carbonate. The palladium content is usually in the range from 0.5 to 5% by weight and in particular in the range from 1 to 2% by weight, based on the carrier material. The catalysts are usually employed in poisoned form; the poisoning can be carried out, for example, by treatment with quinoline and/or lead (II) acetate (see also H. Lindlar et al., Org. Synth. Coll. Vol. V, 1973, p. 880). The reaction is usually carried out in an organic solvent. Suitable organic solvents include aromatic hydrocarbons, such as benzene, toluene, xylenes, cumene, aliphatic hydrocarbons, such as n-hexane, ethers, such as tetrahydrofuran, methyl tert-butyl ether, chlorinated hydrocarbons, such as dichloromethane and dichloroethane, alkanols, such as methanol, ethanol and the like, and also esters, for example ethyl acetate. Also suitable are mixtures of the solvents mentioned above. The hydrogenation is usually carried out at temperatures in the range from-10 to 150°C and in particular in the range from 10 to 50°C.

Alternatively, isothiazole compounds of the formula 11 in which R2 is C (R2a) =C (R2b) (R2C) can also be prepared by reaction of the 4-haloisothiazole IV with a (semi) organometallic olefin compound Z-C (R2a) =C (R2b) (R2C), for example a vinylboronic acid (ester) compound (Z = B (OR) 2; R = C1-C6-alkyl) in the sense of a Suzuki reaction, a trialkylvinylstannane (Z = SnR3 ; R = C4-C6-alkyl) in the sense of a Stille coupling, or an olefin H2C=CH-Rzb in the sense of a Heck reaction. Such processes are known to the person skilled in the art, for example from the review articles in Org. React. 1982 (27) pp. 345-390, Acc. Chem. Res. 1995,28, pp. 2-7 (Heck reaction); Angew. Chem.

1998 (96), pp. 504-519 (Stille reaction); Chem. Rev. 1995 (95), pp. 2457-2483 (Suzuki coupling) and the literature cited therein, and they can be employed in a manner analogous to the preparation of the compounds li. The reaction conditions are essentially comparable to those of the reaction of IV with an alkyne.

The starting materials of the formula III required for preparing the compounds I are known from the literature, for example from the prior art cited at the outset or from WO- A 97/18198, WO-A 98/02424, DE-A 198 38 708 or WO-A 02/059118, or they can be prepared in accordance with the literature cited therein.

The compounds I and their salts are suitable for controlling plant-damaging microorganisms, in particular harmful fungi (i. e. as fungicides) and for controlling animal plant pests, i. e. as pesticides.

They are distinguished in particular by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, especially from the class of the Ascomycetes, Deuteromycetes, Oomycetes and Basidiomycetes. Some are systemically effective and can be used in crop protection as foliar and soil fungicides.

They are particularly important in the control of a multitude of fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, corn, grass, bananas, cotton, soybean, coffee, sugar cane, vines, fruits and ornamental plants, and vegetables, such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

They are especially suitable for controlling the following plant diseases: Alternaria species on fruit and vegetables, Bipolaris and Drechslera species on cereals, rice and lawns, Blumeria graminis (powdery mildew) on cereals, Botrytis cinerea (gray mold) on strawberries, vegetables, ornamental plants and grapevines, # Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbits, # Fusarium and Verticillium species on various plants, Mycosphaerella species on cereals, bananas and peanuts, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on grapevines, Podosphaera leucotricha on apples, # Pseudocercosporella herpotrichoides on wheat and barley, # Pseudoperonospora species on hops and cucumbers, # Puccinia species on cereals, Pyricularia oryzae on rice, Rhizoctonia species on cotton, rice and lawns, Rhynchosporium secalis leaf blotch on cereals, # Septoria tritici and Stagonospora nodorum on wheat, # Uncinula necator on grapevines, # Ustilago species on cereals and sugar cane, and

Venturia species (scab) on apples and pears.

The compounds I are also suitable for controlling harmful fungi, such as Paecilomyces variotii, in the protection of materials (e. g. wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.

The compounds of the formula I are furthermore suitable for the effective control of animal pests from the class of the insects, arachnids and nematodes. They can be used for controlling animal pests in crop protection and in the sectors of hygiene and of protection of stored products and in the veterinary sector. They are particularly suitable for controlling the following animal pests: Insects from the order of the lepidopterons (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Spodoptera eridania, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis, beetles (Coleoptera), e. g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, lps typographus, Lema bilineata, Lema melanopus, Leptinotarsa

decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp. , Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria, dipterons (Diptera), e. g. Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula oleracea and Tipula paludosa, thrips (Thysanoptera), e. g. Frankliniella fusca, Frankliniella occidentalis, Frarikliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci, hymenopterans (Hymenoptera), e. g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta, heteropterans (Heteroptera), e. g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis and Thyanta perditor, w homopterans (Homoptera), e. g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Cerosipha gossypii (Aphis gossypii), Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avanea, Sogatella furcifera, Trialeurodes vaporariorum, Toxoptera aurantiiand and Viteus vitifolii, termites (Isoptera), e. g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,

orthopterans (Orthoptera), e. g. Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus, Arachnoidea such as arachnids (Acarina), e. g. Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Paratetranychus pilous, Dermanyssus gallinae, Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, nematodes such as root ball nematodes, e. g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e. g. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stem and leaf nematodes, e. g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidbrus elongatus, Radopholus similis, Rotylenchus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglects, Pratylenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The compounds I are employed by treating the plant-damaging microorganisms or the animal pests or the plants, seeds, materials or soil to be protected from attack by these harmful organisms with an effective amount of the active compounds. The application can be carried out both before and after the infection/infestation of the materials, plants or seeds by the harmful organisms.

The compositions according to the invention generally comprise between 0.1 and 95%, preferably between 0.5 and 90%, by weight of active compound.

When employed in plant protection, the amounts applied are, depending on the kind of effect desired, between 0.01 and 2.0 kg of active compound per ha.

In seed treatment, amounts of active compound of 0.001 to 1 g, preferably 0.01 to 0.05 g, per kilogram of seed are generally required.

When used in the protection of materials or stored products, the amount of active compound applied depends on the kind of application area and on the desired effect.

Amounts customarily applied in the protection of materials are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active compound per cubic meter of treated material.

Under outdoor conditions, the application rate of active compound for controlling animal pests are from 0.1 to 2.0, preferably from 0.2 to 1.0, kg/ha.

The compounds I can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application form depends on the particular purpose; in each case, it should ensure a fine and uniform distribution of the compound according to the invention.

The formulations are prepared in a known way, e. g. by extending the active compound with solvents and/or carriers, if desired using emulsifiers and dispersants, it being possible, when water is the diluent, also to use other organic solvents as auxiliary solvents. Suitable auxiliaries for this purpose are essentially : solvents, such as aromatics (e. g. xylene), chlorinated aromatics (e. g. chiorobenzenes), paraffins (e. g. petroleum fractions), alcohols (e. g. methanol, butanol), ketones (e. g. cyclohexanone), amines (e. g. ethanolamine, dimethylformamide) and water; carriers, such as ground natural minerals (e. g. kaolins, clays, talc, chalk) and ground synthetic ores (e. g. highly dispersed silicic acid, silicates); emulsifiers, such as nonionic and anionic emulsifiers (e. g. polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates) and dispersants, such as lignosulfite waste liquors and methylcellulose.

Suitable surfactants are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid and dibutyl- naphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates and fatty acids, and alkali metal and alkaline earth metal salts thereof, salts of sulfate fatty alcohol glycol ethers, condensation products of sulfonate naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxy- ethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol and nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Petroleum fractions having medium to high boiling points, such as kerosene or diesel fuel, furthermore coal tar oils, and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e. g. benzene, toluene, xylene, paraffin, tetrahydro- naphthalene, alkylated naphthalenes or derivatives thereof, methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene or isophorone, or highly polar solvents, e. g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water, are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions.

Powders, preparations for broadcasting and dusts can be prepared by mixing or mutually grinding the active substances with a solid carrier.

Granules, e. g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are, e. g. , mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, e. g., ammonium sulfate, ammonium phosphate, ammonium nitrate or ureas, and plant products, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

The formulations generally comprise between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight, of the active compound. The active compounds are employed therein in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples for formulations are: I. 5 parts by weight of a compound according to the invention are intimately mixed with 95 parts by weight of finely divided kaolin. In this way, a dust comprising 5% by weight of the active compound is obtained.

II. 30 parts by weight of a compound according to the invention are intimately mixed with a mixture of 92 parts by weight of pulverulent silica gel and 8 parts by weight of liquid paraffin, which had been sprayed onto the surface of this silica gel. In this way, an active compound preparation with good adhesive properties (active compound content 23% by weight) is obtained.

III. 10 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the addition

product of 8 to 10 mol of ethylene oxide with 1 mol of the N-monoethanolamide of oleic acid, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil (active compound content 9% by weight).

IV. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition product of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 5 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil (active compound content 16% by weight).

V. 80 parts by weight of a compound according to the invention are intimately mixed with 3 parts by weight of the sodium salt of diisobutyinaphthalene-a-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of pulverulent silica gel and are ground in a hammer mill (active compound content 80% by weight).

Vl. 90 parts by weight of a compound according to the invention are mixed with 10 parts by weight of N-methyl-a-pyrrolidone and a solution is obtained which is suitable for use in the form of very small drops (active compound content 90% by weight).

Vil. 20 parts by weight of a compound according to the invention are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition product of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the addition product of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100 000 parts by weight of water and finely dispersing it therein, an aqueous dispersion is obtained comprising 0.02% by weight of the active compound.

Vill. 20 parts by weight of a compound according to the invention are intimately mixed with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pulverulent silica gel and are ground in a hammer mill. A spray emulsion comprising 0.1 % by weight of the active compound is obtained by fine dispersion of the mixture in 20 000 parts by weight of water.

The active compounds can be used as such, in the form of their formulations or of the application forms prepared therefrom, e. g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts,

preparations for broadcasting or granules, by spraying, atomizing, dusting, broadcasting or watering. The application forms depend entirely on the intended uses; they should always ensure the finest possible dispersion of the active compounds according to the invention.

Aqueous use forms can be prepared from emulsifiable concentrates, pastes or wettable powders (spray powders, oil dispersions) by addition of water. To prepare emulsions, pastes or oil dispersions, the substances can be homogenized in water, as such or dissolved in an oil or solvent, by means of wetting agents, tackifiers, dispersants or emulsifiers. However, concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil can also be prepared, which concentrates are suitable for dilution with water.

The concentrations of active compound in the ready-for-use preparations can be varied within relatively wide ranges. In general, they are between 0.0001 and 10%, preferably between 0. 01 and 1 %.

The active compounds can also be used with great success in the ultra low volume (ULV) process, it being possible to apply formulations with more than 95% by weight of active compound or even the active compound without additives.

Oils of various types, herbicides, fungicides, other pesticides and bactericides can be added to the active compounds, including if need be not until immediately before use (tank mix). These agents can be added to the preparations according to the invention in a weight ratio of 1: 10 to 10: 1.

The preparations according to the invention can, in the application form as fungicides, also be present together with other active compounds, e. g. with herbicides, insecticides, growth regulators, fungicides or also with fertilizers. On mixing the compounds I or the preparations comprising them in the application form as fungicides with other fungicides, in many cases an expansion of the fungicidal spectrum of activity is obtained.

The following list of fungicides, with which the compounds according to the invention can be used in conjunction, is intended to illustrate the possible combinations but does not limit them: acylaianines, such as benalaxyl, metalaxyl, ofurace or oxadixyl, amine derivatives, such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine or tridemorph,

anilinopyrimidines, such as pyrimethanil, mepanipyrim or cyprodinil, 'antibiotics, such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin, 'ago azoles, such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochloraz, prothioconazole, tebuconazole, triadimefon, triadimenol, triflumizole or triticonazole, dicarboximides, such as iprodione, myclozolin, procymidone or vinclozolin, dithiocarbamates, such as ferbam, nabam, maneb, mancozeb, metam, metiram, propineb, polycarbamate, thiram, ziram or zineb, heterocyclic compounds, such as anilazine, benomyl, boscalid, carbendazim, carboxin, oxycarboxin, cyazofamid, dazomet, dithianon, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazid, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole or triforine, copper fungicides, such as Bordeaux mixture, copper acetate, copper oxychloride or basic copper sulfate, nitrophenyl derivatives, such as binapacryl, dinocap, dinobuton or nitrophthal- isopropyl, phenylpyrroles, such as fenpiclonil or fludioxonil, sulfur, other fungicides, such as acibenzolar-S-methyl, benthiavalicarb, carpropamid, chlorothalonil, cyflufenamid, cymoxanil, dazomet, diclomezine, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamid, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, tolclofos-methyl, quintozene or zoxamide, strobilurins, such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim- methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin or trifloxystrobin, 'su sulfenic acid derivatives, such as captafol, captan, dichlofluanid, folpet or tolylfluanid, cinnamamides and analogous compounds, such as dimethomorph, flumetover or flumorph.

Synthesis examples

The procedures described in the following synthesis example were used to prepare further compounds I by appropriate modification of the starting compounds. The compounds thus obtained are listed in the following table 1, together with physical data.

Example 1: N- (4-Ethynyl-3-methylisothiazol-5-yl)-2- [4- (4-nitrophenoxy) phenyl]- acetamide 1.1 : 4-lodo-3-methylisothiazol-5-ylamine 87 g (765 mmol) of 3-methylisothiazol-5-ylamine are dissolved in 3 ! of carbon tetrachloride. The solution is warmed to 30°C, 172 g of N-iodosuccinimide are added and the mixture is then stirred at 30°C for 20 h. For work-up, 800 mi of methyl ter-butyl ether are added, insoluble components are filtered off and the filtrate is washed with water. The organic phase is dried over sodium sulfate and evaporated to dryness, giving the iodine compound in a yield of 65 g (33% of theory).

'H-NMR (CDCI3) : 5 2.43 (s, 3H), 4.80, (br. s. , 2H) 1.2 : 3-Methyl-4-trimethylsilylethynyl-isothiazol-5-ylamine 60 g (252 mmol) of 4-iodo-3-methylisothiazol-5-ylamine are, together with 49 g (500 mmol) of trimethylsilylacetylene, 2.1 g of tetrakis (triphenylphosphine)- palladium (0) and 2.1 g of triphenylphosphine, dissolved in 800 mi of triethylamine and 300 ml of tetrahydrofuran. A mixture of 2.1 g of copper (l) bromide and 4.2 g of lithium bromide in 350 ml of tetrahydrofuran is added, and the mixture is heated at 55°C for 20 h. For work-up, ice-water is added and the resulting mixture is extracted repeatedly with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to dryness, giving the acetylene compound in a yield of 44.9 g (54% of theory).

'H-NMR (CDCI3) : 6 0. 13 (s. 9H), 2.38 (s, 3H), 4.90, (br. s. , 2H) 1.3 : 4-Ethynyl-3-methyl-isothiazol-5-ylamine 44.9 g (765 mmol) of 3-methyl-4-trimethylsilylethynyl-isothiazol-5-ylamine are dissolved in 900 ml of dichloromethane. The solution is cooled to 0°C, 250 ml of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added and the mixture is then stirred at room temperature for 48 h. For work-up, the reaction mixture is concentrated and the residue is chromatographed on silica gel (mobile phase cyclohexane : ethyl acetate 8: 2 v/v), giving the ethynyl compound in a yield of 14.0 g (47% of theory).

'H-NMR (CDC13) : 5 2.36 (s, 3H), 3.48 (s, 1 H), 5.05, (br. s. , 2H) 1.4 : N- (4-Ethynyl-3-methylisothiazol-5-yl)-2- [4- (4-nitrophenoxy) phenyl] acetamide

22.1 g (81 mmol) of [4- (4-nitrophenoxy) phenyl] acetic acid are dissolved in 0.5 I of dichloromethane, and a few drops of dimethylformamide are added. 11.3 g (89 mmol) of oxalyl chloride are added dropwise, and the mixture is heated under reflux for 2 h. For work-up, several portions of toluene are added, and during the addition, the mixture is concentrated. The residue (19.6 g, about 67 mmol) is dissolved in 120 ml of toluene, the solution is added to a mixture of 4-ethynyl-3- methyl-isothiazol-5-ylamine, 250 ml of toluene and 125 mi of pyridine, and a small amount of dimethylaminopyridine is added. The solution is stirred at 40°C for 2 h. The solution is then concentrated, the residue is partitioned between ethyl acetate and water and the organic phase is washed successively with 10% strength aqueous hydrochloric acid and aqueous sodium bicarbonate solution.

After drying over magnesium sulfate, the organic phase is concentrated, giving 13.5 g of the title compound (37% of theory). tH-NMR (CDCI3) : S 2.40 (s, 3H), 3.49 (s, 1 H), 3.92 (s, 2H), 7.02 (d, 2H), 7.18 (d, 2H), 7.42 (d, 2H), 8.22 (d, 2H), 8.31 (br. s., 1 H) Example 2: N- (4-Ethynyl-3-methylisothiazol-5-yl)-2- [4-trifluoromethoxyphenyl]- acetamide 0.8 g (3.6 mmol) of 4-trifluoromethoxyphenylacetic acid is dissolved in 15 ml of tetrahydrofuran, and 0.6 g (4.0 mmol) of carbonyldiimidazole is added. The mixture is heated under reflux for 15 minutes, a solution of 0.5 g (3.6 mmol) of 4-ethynyl-3- methyl-isothiazol-5-ylamine from Example 1.3 in 10 ml of tetrahydrofuran is then added dropwise at reflux, and the reaction mixture is heated for a further 3 hours and stirred at room temperature overnight. The reaction mixture is concentrated, 30 mi of a 5% strength aqueous sodium hydroxide solution are then added and the aqueous reaction mixture is added to 100 ml of saturated ammonium chloride solution. The resulting mixture is extracted three times with ethyl acetate. The organic phase is dried and then concentrated, and the resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 9: 1 v/v), giving 0.3 g of the title compound (25% of theory) of melting point 100-115°C.

H-NMR (CDCI3) : S 2.40 (s, 3H), 3.40 (s, 1 H), 3.90 (s, 2H), 7.25 (m, 2H), 7.35 (m, 2H), 8.90 (br. s., 1 H).

The compounds of the formula I {R1 = CH3, R3 = H, R5 = H} listed in Table 1 below were prepared in an analogous manner.

Table 1: Example R2 R4 R6b R6c R6d m.p. [°C] or consistency; 1H-NMR (CDCl3) [ppm] 1 ethynyl H H 4-nitrophenoxy H 2.40 (s, 3H), 3.49 (s, 1H), 3.92 (s, 2H), 7.02 (d, 2H), 7.18 (d, 2H), 7.42 (d, 2H), 8.22 (d, 2H), 8.31 (br. s., 1H) 2 ethynyl H H trifluoromethoxy H 100-115; 2.40 (s, 3H), 3.40 (s, 3H), 3.90 (s, 2H), 7.25 (m, 2H), 7.35 (m, 2H), 8.90 (br. s., 1H); 3 ethynyl H H 4-cyanophenoxy H 165-167 4 ethynyl H H 4-chlorophenoxy H 121-122 5 ethynyl H benzyloxy methoxy H 132-135; 2.40 (s, 3H), 3.40 (s, 1H), 3.75 (s, 2H), 3.90 (s, 3H), 5.15 (s, 2H), 6.85 (s, 1H), 6.90 (dd, 2H), 7.25 (t, 1H), 7.35 (t, 2H), 7.40 (d, 2H), 8.45 (s, 1H); 6 ethynyl H H 4-trifluoromethyl- H 2.42 (s, 3H), 3.43 (s, 1H), 3.96 (s, 2H), 7.45 phenyl (d, 2H), 7.68 (m, 6H), 8.39 (br. s., 1H) Example R2 R4 R6b R6c R6d m.p. [°C] or consistency; 1H-NMR (CDCl3) [ppm] 7 ethynyl H methoxy benzyloxy H 141-144; 2.4 (s, 3H), 3.27 (s, 1H), 3.77 (s, 2H), 3.88 (s, 3H), 5.17 (s, 2H), 6.8 (d, 1H), 6.83 (s, 1H), 6.92 (d, 1H), 7.3 (m, 1H), 7.35 (m, 2H), 7.43 (m, 2H), 8.58 (s, 1H); 8 ethynyl H H tert-butyl H 1.33 (s, 9H), 2.4 (s, 3H), 2.68 (s, 1H), 3.87 (s, 2H), 7.28 (d, 2H), 7.43 (m, 2H); 9 ethynyl CH3 H CH2CH(CH3)2 H 139-141; 0.92 (d, 6H), 1.66 (m, 3H), 1.87 (m, 1H), 2.42 (s, 3H), 2.47 (d, 2H), 3.33 (s, 1H), 3.87 (m, 1H), 7.2 (d, 2H), 7.25 (d, 2H), 8.25 (br. s., 1H); 10 ethynyl H H benzyloxy H 2.42 (d, 3H), 2.67 (s, 1H), 3.80 (m, 2H), 5.08 (m, 2H), 7.02 (m, 2H), 7.2 (m, 1H), 7.3 (m, 2H), 7.42 (m, 4H), 8.35 (br.s., 1H); 11 ethynyl H H acetyl H 165-167; 2.43 (s, 3H), 2.62 (s, 3H), 3.47 (s, 1H), 3.93 (s, 2H), 7.62 (d, 2H), 8.00 (d, 2H), 8.33 (br.s., 1H); 12 ethynyl H methoxy methoxy H 159-162; 2.42 (s, 3H), 3.42 (s, 1H), 3.83 (s, 2H), 3.93 (s, 6H), 6.83 (m, 1H), 6.9 (m, 2H) Example R R4 R6b R6c R6d m. p. [°C] or consistency ; 'H-NMR (CDCI3) [ppm] 13 ethynyl H H H 141-142 ; CH, CH, 2. 23 (s, 3H), 2. 35 (s, 3H), 2. 42 (s, 3H), 3. 42 'CH 3 (s, 1 H), 3. 88 (s, 2H), 5. 20 (s, 2H), 7. 17 (d, 2H), 7. 32 (m, 4H), 7. 7 (d, 2H), 14 propyn-1-yl H H 4-cyanophenoxy H 125-126 : 15 isopropenyl H H 4-cyanophenoxy H oil ; 16 propyn-1-yl H H 4-nitrophenoxy H 150-155, 17 isopropenyl H H 4-nitrophenoxy H resin 18 ethynyl H H trifluoromethyl H 138-139 ; 19 ethynyl H trifluoromethyl H H 145-150 ; 20 ethynyl H trifluoromethyl fluoro H 143-146 21 ethynyl H fluoro trifluoromethyl H 142-145 ; 22 ethynyl H trifluoromethyl H trifluoromethyl 150-153 ; 23 ethynyl H H 4-trifluoromethyl-H oil phenoxy 24 ethynyl H H nitro H 175-178 25 3-methoxy-H H trifluoromethoxy H resin propyn-1-yl 26 3-hydroxy-H H 4-nitrophenoxy H 65-75 3-methyl- butyn-1-yl m.p.: melting point

Assessment of the activity against animal pests The activity of the compounds of the formula I according to the invention against animal pests was demonstrated by the following assessments: The active compounds of the formula I were formulated as follows : - To assess the activity against Aphis gossypii, Tetranychus urticae, Myzus persi- cae and Aphis fabae as a solution in a mixture of 50 parts by volume of water and 50 parts by volume of acetone with 100 ppm of Kinetik0 (emulsifier).

- To assess the activity against Spodoptera eridania as a solution in a mixture of 35% acetone and water having a content of active compound of 10 000 ppm, which solution was, if required, diluted with water.

- To assess the activity against Nilaparvata lugens and Sogatella furcifera as a solution in acetone: water 20: 80 v/v to which a surfactant (Alkamuls EL 620) had been added in an amount of 0. 1 % by volume.

Activity against Aphis gossypii Cotton plants of the cultivar"Deltapine"were, in the cotyledon stage, infected with about 100 laboratory aphids by placing infected leaf sections on the surface of the test plants. Leaf sections were removed after 24 h. The cotyledons of the plants were briefly dipped into solutions of the test compounds. The mortality rate of the aphids on the treated plants, compared to the control plants, was determined after five days.

In the assessment, the compounds of Examples 1,2, 3,4 and 7 caused, at 300 ppm, a mortality of about 100% compared to the untreated plants.

Activity against Tetranychus urticae Plants of lima bean in the one-leaf stage (cultivar"Henderson") were infected with about 100 mites which had been cultivated in the laboratory per leaf by placing infected leaf sections onto the surface of the test plants. The leaf sections were removed after 24 h. The leaf surface of the plants treated in this manner was briefly dipped into a so- lution of the test compound. The mortality rate of the mites was determined after five days.

In this assessment, the compounds of Examples 1,2, 3,4 and 7 caused, at a concen-

tration of active compound of 300 ppm, a mortality of about 100%, compared to un- treated control plants.

Activity against Myzus persicae Bell-pepper plants in the two-leaf stage (cultivar"California Wonder") were infected with about 40 aphids, which had been cultivated in the laboratory, by placing infected leaf sections onto the surface of the test plants. The leaf sections were removed after 24 h.

Leaves of the treated plants were dipped into a solution of the test compound. The mortality of the aphids on the treated plants in comparison to the mortality of the control plants was determined after five days.

In this assessment, the compounds of Examples 1,2, 3,4 and 7 caused, at a concen- tration of active compound of 300 ppm, a mortality of about 100%, compared to un- treated control plants.

Activity against Aphis fabae Nasturtium plants in the one-leaf stage (cultivar"Mixed Jewel") were infected with about 25 aphids, which had been cultivated in the laboratory, by placing infected leaf pieces onto the surface of the test plants. The leaf sections were removed after 24 h.

The leaves and stems of the test plants were dipped into a solution of the test com- pound. The mortality of the aphids was determined after three days.

In this assessment, the compounds of Examples 1,2, 3, 4 and 7 caused, at a concen- tration of active compound of 300 ppm, a mortality of 100% compared to the untreated control plants.

Activity against Spodoptera eridania (second larval stage) The leaves of two Sieva lima bean plants at the first expanded two-leaf stage, raised in a square plastic pot with an edge of 3.8 cm were, with agitation, dipped into the solu- tion of active compound for three seconds and then dried in a fume cupboard. The pot was then transferred into a zipped plastic bag and infected with 10 caterpillars of the second larval stage. After five days, the mortality, reduced feed intake and other inter- ferences with normal development were examined.

In this assessment, the compounds of Examples 1,2, 3,4 and 7 caused, at a concen- tration of active compound of 300 ppm, a mortality of at least 75% compared to the untreated plants.

Activity against Nilaparvata lugens and Sogatella furcifera Three-to four-week-old rice plants were sprayed with 10 ml of the solution of active compound using a hand-operated atomizer (Devilbiss atomizer) with a pressure of 1.7 bar. The test plants were allowed to dry for 1 h and covered with hoods. The plants were inoculated with ten adult animals of each species (5 male and 5 female) and kept at 25 to 27°C and 50 to 60% atmospheric humidity for three days. The mortality was determined 24,48 and 72 h after the treatment. Each treatment was repeated once. In this assessment, the compounds of Example 1 caused, at 500 ppm, a mortality of more than 75% of the species Nilaparvata lugens and of more than 75% of the species Sogatella furcifera.