MXPA00002272A - Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives - Google Patents

Abstract

Novel pyrimidin-4-one and pyrimidin-4-thione derivatives of formula (I) wherein A is phenyl, thienyl (including all 3 isomers), thiazolyl or pyridyl;X is oxygen or sulfur;R1 is hydrogen, halogen or trimethylsilyl;R2 is hydrogen, halogen or trimethylsilyl;and at least one of R1 and R2 is not hydrogen;R3 is C1-C6alkyl, C1-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, -(CH2)n-C3-C8cycloalkyl which are unsubstituted or substituted by halogen, C1-C6alkyl or C1-C6haloalkyl;C1-C4alkoxy-C1-C6alkyl;C1-C4alkoxy-C2-C6alkenyl;C1-C4alkoxy-C2-C6alkynyl;C1-C4alkylthio-C1-C6alkyl;C1-C4alkylthio-C2-C6alkenyl;C1-C4alkylthio-C2-C6alkynyl;mono-C1-C4alkylamin-C1-C6alkyl;mono-C1-C4alkylamin-C2-C6alkenyl;mono-C1-C4alkylamin-C2-C6alkynyl;-(CH2)n-C1-C4alkoxy-C3-C6cycloalkyl;-(CH2)n-C1-C4alkylthio-C3-C6cycloalkyl;-(CH2)n-mono-C1-C4alkylamin-C3-C6cycloalkyl;or N=CR9R10;n is 1, 2, 3 or 4;R4,R5, R6, R7 and R8 are each independently of the other hydrogen, C1-C4alkyl, C1-C4haloalkyl or halogen, wherein at least one of the substituents R4 - R8 must be different from hydrogen;and R9 is hydrogen, C1-C6alkyl, C3-C7 cycloalkyl, pyridyl, furyl, thienyl or phenyl which is unsubstituted or mono to pentasubstituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;R10 is hydrogen, C1-C6alkyl, C3-C7cycloalkyl, pyridyl, furyl, thienyl or phenyl which is unsubstituted or mono to pentasubstituted by halogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy or C1-C6haloalkoxy;and at least one of R9 and R10 is not hydrogen. The novel compounds have plant-protective properties and are suitable for protecting plants against infestation by phytopathogenic microorganisms, in particular fungi.

Description

nff.BTVapos T Ptt? TMtnttj-9-OXT-4-ON? Y PTRTMTnTN-P-nYT-l-TTpM-- The present invention relates to novel derivatives of pyrimidin-4-one and pyrimidin-4-thione of the formula I, which have pesticidal activity, in particular fungicidal activity: wherein: A is phenyl, thienyl (including the 3 isomers) thiazolyl, or pyridyl; X is oxygen or sulfur; Ri is hydrogen, halogen, or trimethylsilyl; R2 is hydrogen, halogen, or trimethylsilyl; when less one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to carbon atoms, haloalkynyl of 2 to 6 carbon atoms, (CH 2) n-cycloalkyl of 3 to 8 carbon atoms which are unsubstituted. or mono- to tri-substituted by halogen, alkyl of 1 to carbon atoms, or haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; alkoxy of 1 to 4 carbon atoms-alkenyl of 2 to carbon atoms; alkoxy of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkenyl of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkenyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkynyl of 2 to 6 carbon atoms; -CH2) n-alkoxy of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) n-thioalkyl of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) rr-monoalkyl of 1 to 4 carbon atoms-aminocycloalkyl of 3 to 6 carbon atoms; or n is 1, 2, 3, or 4; R4, R5, R6, R7 and Rs are each independently of the others, hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or halogen, wherein at least one of the substituents R4- R8 must be different from hydrogen; and R9 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 atoms carbon, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; Rio is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 carbon atoms. carbon, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; and at least one of Rg and Rio is not hydrogen. The invention also relates to the preparation of these compounds, to agrochemical compositions comprising as active ingredient at least one of these compounds, as well as to the use of the active ingredients or compositions for the control of pests, in particular as fungicides, in agriculture and horticulture. The compounds I, and optionally their tautomers, can be obtained in the form of their salts. Because the compounds I have at least one basic center, they can form, for example, acid addition salts. Acid addition salts, for example, are formed with mineral acids, usually sulfuric acid, a phosphoric acid or a hydrogen halide, with organic carboxylic acids, usually acetic acid, oxalic acid, alonic acid, maleic acid, furaric acid or phthalic acid, with hydroxycarboxylic acids, usually ascorbic acid, lactic acid, malic acid, tartaric acid, or citric acid, or with benzoic acid, or with organic sulfonic acids, usually methanesulfonic acid or p-toluenesulfonic acid. Along with at least one acid group, the compounds of the formula I can also form salts with bases. Salts with suitable bases are, for example, metal salts, usually alkali metal salts or alkaline earth metal salts, for example sodium salts, potassium salts, or magnesium salts, or salts with ammonia or with an organic amine, for example morpholine, piperidine, pyrrolidine, a mono-, di-, or tri-alkylamine, usually ethylamine, diethylamine, triethylamine, or dimethylpropylamine, or a mono-, di-, or tri- idroxyalkylamine, usually mono- di-, or tri-ethanolamine. Where appropriate, the formation of the corresponding internal salts is also possible. Within the scope of this invention, agrochemically acceptable salts are preferred. Where asymmetric carbon atoms are present in the compounds of the formula I, these compounds are in an optically active form. Due to the presence of double bonds, the compounds can be obtained in the form [E] and / or [Z]. Atropisomerism may also occur. The invention relates to pure isomers, such as enantiomers and diastereoisomers as well as to all possible mixtures of isomers, for example mixtures of diastereomers, racemates or mixtures of racemates. The general terms used hereinbefore, and hereinafter, have the following meanings, unless defined otherwise: The alkyl groups by themselves, or as a structural element of other groups, such as alkoxy, are, according to the number of carbon atoms, straight or branched chain, and will normally be methyl, ethyl, normal propyl, isopropyl, normal butyl, secondary butyl, isobutyl, tertiary butyl, normal amyl, tertiary amyl, -hexyl, or 3-hexyl. It will be understood that alkenyl means straight or branched chain alkenyl, such as allyl, methallyl, 1-ethylvinyl, or but-2-en-1-yl. Preferred alkenyl radicals contain from 3 to 4 carbon atoms in the chain. In the same way, alkynyl can be, according to the number of carbon atoms, straight or branched chain, and is usually propargyl, but-1-in-1-yl, or but-1-in-3 -ilo. The preferred meaning is propargyl. The halogen and halo substituents will be generally understood as fluorine, chlorine, bromine, or iodine. Preferred meanings are fluorine, chlorine, or bromine. Haloalkyl may contain identical or different halogen atoms, usually fluoroethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethylene, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2, 2, 2- trichloroethyl, 3, 3, 3-trifluoropropyl. Cycloalkyl is, depending on the size of the ring, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl. Preferred compounds are those of the formula I, wherein: A is thienyl, including the three isomers, and X is oxygen (subgroup A). Within the scope of this subgroup A, compounds of the formula I are preferred where: R x is hydrogen, fluorine, chlorine, bromine, or iodine; R2 is hydrogen, fluorine, chlorine, bromine, or iodine; at least one of R and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, or CH2-cycloalkyl of 3 to 4 carbon atoms, which are unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R4, R5, R6, R7 and R8 are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup B). Within the scope of subgroup B, particularly preferred are compounds of formula I wherein: R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, each of which is unsubstituted or substituted by chlorine or bromine; or -CH2-cycloalkyl of 3 to 6 carbon atoms, which is unsubstituted or substituted by fluorine, chlorine, bromine, or iodine; R, R5, Re, 7, and s are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup C). A special group within the scope of subgroup C is that of compounds of formula I wherein: Ri is hydrogen, chlorine, or bromine; R2 is hydrogen, chlorine, or bromine; at least one of Ri and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms or CH2-cyclopropyl; R, R5, R6, R, and Rs are each independently of the others, hydrogen, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup D). A preferred group within the scope of subgroup D is that of the compounds of formula I wherein: A is thienyl [2.3-d], R3 is alkyl of 3 to 4 carbon atoms, R4, Rs, Re, 7 and Rs are each independently of the others, hydrogen, chlorine, bromine, methyl, or CF3, wherein at least one of the substituents R4-Rs must be different from hydrogen (subgroup E). Another preferred group within the scope of subgroup D is that of the compounds of formula I wherein: A is thienyl [3.2-d]; R3 is alkyl of 3 to 4 carbon atoms; R4, Rs, Re, 7, and Re are each independently of the others, hydrogen, chlorine, bromine, methyl, or CF3, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup F). Other preferred compounds are those of the formula I, wherein: A is phenyl, and X is oxygen (subgroup G). Within the scope of subgroup G, the compounds of formula I are preferred wherein: Ri is hydrogen, fluorine, chlorine, bromine, or iodine; R2 is hydrogen, fluorine, chlorine, bromine, or iodine; at least one of Ri and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, or CH2-cycloalkyl of 3 to 4 carbon atoms, which are unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R4, R5, R6, R7 and R8 are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup H). Within the scope of subgroup H, compounds of formula I are particularly preferred wherein: R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, T * each of which is unsubstituted or substituted by chlorine or bromine; or -CH2-cycloalkyl of 3 to -6 carbon atoms, which is unsubstituted or substituted by fluorine, chlorine, bromine, or iodine; R4, Rs, R6, R7, and R8 are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup J). A special group within the scope of subgroup J is that of the compounds of formula I wherein: R is hydrogen, chlorine, or bromine; R2 is hydrogen, chlorine, or bromine; at least one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms or CH2-cyclopropyl; R4, R5, R6, R7, and R8 are each independently of the others, hydrogen, chlorine, bromine, iodine, or alkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup K). Other preferred compounds are those of the formula 1 wherein: A is pyridyl, and X is ox: oxygen (subgroup L). Within the scope of the subgroup L, the compounds of the formula I are preferred in which: R x is hydrogen, fluorine, chlorine, bromine, iodine; R2 is hydrogen, fluorine, chlorine, bromine, or iodine; at least one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, or CH2-cycloalkyl of 3 to 4 carbon atoms, which are unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; R4, Rs, R6, R7 and R8 are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-8 must be different from hydrogen (subgroup M). Within the scope of the M subgroup, particularly preferred are compounds of the formula I wherein: R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, each of which is unsubstituted or substituted by chlorine or bromine; or -CH2-cycloalkyl of 3 to 6 carbon atoms, which is unsubstituted or substituted by fluorine, chlorine, bromine, or iodine; R4, R5, Re, R7, and Rs are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup N). A special group within the scope of subgroup N is that of the compounds of formula I wherein: R x is hydrogen, chlorine, or bromine; R2 is hydrogen, chlorine, or bromine; at least one of Ri and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms or CH2-cyclopropyl; R4, R5, R6, R7, and Rs are each independently of the others, hydrogen, chlorine, bromine, iodine, or alkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen (subgroup P). The most preferred compounds of the invention disclosed herein are the following: 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-propyl-3H-quinazolin-4-one (No. 1.7), 6 -bromo-2- (2-methylcyclopropylmethoxy) -3-n-propyl-3H-quinazolin-4-one (No. 1. "22), 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-butyl -3H-quinazolin-4-one (No. 1.10), 6-bromo-2- (2-methylcyclopropylmethoxy) -3-n-butyl-3H-quinazolin-4-one (No. 1.25), 6-bromo-2 - (1-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2,3-d] pyrimidin-4-one (No. 3.7), 6-chloro-2- (1-methylcyclopropylmethoxy) -3 * -r- propyl-3H-thieno [2,3-d] pyrimidin-4-one (No. 3.6), - 6-bromo-2- (2-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2, 3-d] pyrimidin-4-one (# 3.22), 6-chloro-2- (2-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2,3-d] pyrimidin-4-one (# 3.21), 6- bromo-2- (1-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one (No. 3.10), 6-chloro-2- (1-methylcyclopropylmethoxy) -3-n -butyl-3H-thieno [2,3-d] pyrimidin-4-one (No. 3.9), 6-Bromo-2- (2-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one (no. 3.25), 6-chloro-2- (2-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one (# 3.24) The compounds of the formula I can be prepared as follows : Scheme 1 / 1b) R1 NCS / DMFo alcohols / 75-160 ° C ^ R = H, C-j-Cgalkyl IV 3): * i - X = OS The compounds of the formula I are preferably prepared starting from a-amino-β-carboalkoxy-heterocycles, or heterocycles of α-amino-β-carbocyclic acid, some of which, where Het = thienyl, they are commercially available (2 isomers). Methyl thiophen-2-amino-3-carboxylate can be prepared, for example, according to Acta Pharm. Suecica 1968, volume 5, page 563, according to S. Gronowitz et al. Other heterocycles can be prepared according to literature instructions. For example, the synthesis of ethyl 5-aminothiazole-4-carboxylate and ethyl 5-amino-2-methylthiazole-4-carboxylate is described by Golankiewicz et al. in Tetrahedron 1985, 41, 5989. The reaction of amino-β-carboalkoxyheterocycles or of the a-amino-β-carbocyclic acid heterocycles with thiophosgene (step 1 in Scheme 1), conveniently carried out in the presence of a base, such as NaOH, KOH, CaC03, NaC03, K2C03 , NaHC03, N (Et) 3, pyridine, and others, in solvents, such as CH2C12, CHC13, ether, tetrahydrofuran and others, possibly in a 2-phase mixture consisting of CHCl3 / water or CH2Cl2 / water, or toluene / water , on the temperature scale from 0 ° C to the reflux temperature.

Then the resulting isothiocyanates are converted with primary amines, such as butyl normal-amine, propyl normal-amine, isopropylamine, allylane, propargylamine, cyclopropylamine, and others, in a solvent (ether, tetrahydrofuran, CH2C12, CHC13, benzene, toluene, dimethyl formamide, dimethyl sulfoxide) of 0 ° C at the reflux temperature, in the thioureaheterocyclics IV (step 2 in Scheme 1), which can also be prepared by the reaction of the heterocyclic amines II with isothiocyanatoalkanes such as 1 -isothiocyanatopropane, 1-isothiocyanatobutane, and others, in ethanol, normal propanol, normal butanol, dimethylformamide, dimethylaceformide, or dimethyl sulfoxide as solvents, at temperatures between 50 ° C and reflux temperature (step Ib in Scheme 1). Thioureaheterocycles IV, in most cases, are cyclized immediately (step 3 in Scheme 1). In some cases, cyclization is carried out in the presence of strong bases, such as potassium tertiary butylate, sodium hydride or potassium hydride, in solvents such as tetrahydrofuran, dimethylformamide, or dimethyl sulfoxide, in the therapeutic scale of 20. ° C to 140 ° C. The 2-thioxopyrimidin-4-one derivatives are then deprotonated (using base such as NaOH, NaH, KH, n-BuLi, Na2CO3, K2CO3 and so on), and then S-alkylated by the addition of alkyl halides (halo = Br, I) (step 4 in Scheme 1). The reaction with methyl iodide results in the derivative of 2-methylsulfonyl nilpyrimidin-4-one, which is an important intermediate for the synthesis of pyrimidin-4-ones substituted by alkoxyl and substituted by aminoalkyl. The replacement of the thiomethyl group (steps 5 in Scheme 1) with alkoxy is most preferably performed by its reaction with metal alkoxides, such as NaOCH2- (2-methyl-cyclopropyl), NaOCH2- (1-methyl-cyclopropyl), NaOCH2 - (2, 2-dichloro-cyclopropyl), NaOCH2- (2, 2-difluoro-cyclopropyl), etc., in the corresponding alcohol, tetrahydrofuran, dioxane, or dimethyl sulfoxide as solvent, on the temperature scale of 20 ° C at 150 ° C. The replacement of the 4-one group with sulfur for the group 4-thione (step 6 in scheme 1) is carried out by reaction with P2S5 or Lawesson's reagent in tetrahydrofuran, dioxane, or toluene as solvent, on the temperature scale of 20 ° C at the reflux temperature. The above synthetic route is the first disclosure of the manner of preparing 3H-thieno [2,3-d] -pyrimidin-4-one derivatives within the structural standard of formula I of the present. The invention also relates to the intermediates of formulas IV and V, and especially to those in which A represents thienyl [2.3-d]. The introduction of further substituents into the 5-ring of thienopyrimidin-4-ones can also be conveniently carried out using the metal-organic methodology. Tie-no [3.2-d] -pyrimidin-4-ones and thieno [2,3-d] pyrimidin-4-ones, for example, can be selectively deprotonated in position 6. The bases particularly suitable for this purpose are di - lithium isopropylamide (LDA), lithium cyclohexyl isopropylamide (LICA), or secondary butyl lithium / TMEDA. A large number of the Ri or R2 radicals indicated above can be introduced by the reaction of the resulting anions with electrophile (step 1 in Scheme 2), usually reactive Br2, NBS, F2, ICI, Cl2, F trimethylsilyl chloride .

Scheme 2: Synthesis of special heterocycles E +? 2 = NBS (N-bromosuccinimide), NCS (N-chlorosuccinimide), Cl2 reagents, Br, FCl, F +, similar TMS and Si reagents. In the same way, the following compounds can be prepared in general according to the methods described in Scheme 2: F, gnome 3; Synthesis of special thienopyrimidin-4-one (special methods for the introduction of halogen into the thiophene ring). to T-i * »nr > [2 . -r1] p-i t "i ttH eii n-.l-r.na g For halogenation, 1 to 3 molar equivalents of N-bromosuccinimide or N-chlorosuccinimide (or Cl 2 or Br 2 gas) are used. • The solvent used is, for example, pyridine, in the temperature range from 0 ° C to the reflux. The reaction time is from 1 to 24 hours. a2) "Pure" chlorination method The described reactions are carried out in a manner known per se, for example, in the presence or absence of a suitable solvent or diluent, or of a mixture thereof, if appropriate with cooling, at room temperature or with heating, for example, on the temperature scale from about -20 ° C to the boiling temperature of the reaction medium, preferably on the scale from about -20 ° C to about + 150 ° C, and is required, a closed container, under pressure, in an atmosphere of inert gas and / or under anhydrous conditions. Illustrative examples of these solvents or diluents are: aromatic, aliphatic and alicyclic hydrocarbons, and halogenated hydrocarbons, usually benzene, toluene, xylene, chlorobenzene, bromobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, trichloromethane, dichloroethane, or trichloroethane; ethers, usually diethyl ether, tertiary butyl methyl ether, tetrahydrofuran, or dioxane, ketones, usually acetone or methyl ethyl ketone; alcohols, usually methanol, ethanol, propanol, butanol, ethylene glycol, or glycerol; esters, usually ethyl acetate or butyl acetate; amides, usually N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, or hexamethylphosphoric triamide; nitriles, usually acetonitrile; and sulfoxides, usually dimethyl sulfoxide. Surfaces used in excess, such as triethylamine, pyridine, N-methylmorpholine, or N, N-diethylaniline, can also be used as solvents or diluents. Suitable bases are, for example, alkali metal hydroxide or alkaline earth metal hydroxide, alkali metal hydride or alkaline earth metal hydride, alkali metal amide or alkaline earth metal amide, alkali metal alkanolate or alkaline earth metal alkanolate, carbonate alkali metal or alkaline earth metal carbonate, alkali metal dialkylamide, or alkaline earth metal dialkylamide, or alkali metal alkylsilylamide or alkaline earth metal alkylsilylamide, alkylamines, alkylenediamines, optionally N-alkylated and optionally unsaturated cycloalkylamines, heterocycles basic, ammonium hydroxides, and carbo-cyclic amines. Examples that deserve mention are sodium hydroxide, sodium hydride, sodium amide, sodium methanolate, sodium carbonate, potassium tertiary butanolate, potassium carbonate, lithium di-isopropylamide, potassium bis (trimethylsilyl) amide, hydride of calcium, triethylamine, triethylenediamine, cyclohexylamine, N-cyclohexyl-N, N-dimethylamine, N, N-diethylaniline, pyridine, 4- (N, N-dimethylamino) pyridine, N-methylmorpholine, benzyltrimethylammonium hydroxide, and , 8-diazabicyclo [5.4.0] undec-5-ene (DBU). Quinazolinone derivatives having fungicidal properties are known from Patent Numbers WO-94/26722 or EP-A-276825 and thienopyrimidinones are known from International Publication Number WO-97/02262. Surprisingly, it has now been discovered that the novel compounds of formula I, for practical purposes, have a very convenient spectrum of activities to protect plants against diseases that are caused by fungi, as well as by bacteria and viruses. The compounds of the formula I can be used in the agricultural sector and in related fields as active ingredients for controlling plant pests. The novel compounds are distinguished by their excellent activity at low concentrations of application, to be well tolerated by plants, and to be safe for the environment. They have very useful curative, preventive, and systemic properties, and are used to protect numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy pests that occur in plants or parts of plants (fruits, shoots, leaves, stems, tubers, roots) of different crops of useful plantsAt the same time, the parts of the plants that subsequently grow, for example, of phytopathogenic microorganisms, are also protected, and it is also possible to use the compounds of the formula I as coating agents for the treatment of the propagation material of the plant. plants, in particular seeds (fruit, tubers, grains) and plant cuttings (for example, rice), for protection against fungal infections, as well as against phytopathogenic fungi that occur in the soil. they are, for example, effective against the phytopathogenic fungi of the following classes: imperfect fungus (for example, Botrytis, Pyricularia, Hel inthosporium, Fusarium, Septoria, Cercospora and Al ternarla) and Basidiomycetes (for example Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (for example, Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and the Oomycetes classes (for example, Phytophthora, Pythium, Plasmopara). In addition, the novel compounds of the formula I are effective against phytopathogenic bacteria and viruses (for example, against Xanthomonas spp, Pseudomonas spp, Erwinia amylovor ?, as well as against tobacco mosaic virus). Within the scope of this invention, the target crops to be protected typically comprise the following plant species: cereal (wheat, barley, rye, oats, rice, corn, sorghum, and related species); sweet beets and fodder beets), grapefruit, drupes, and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, and blackberries), leguminous plants (beans, lentils, peas, soybeans); oil plants (rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil plants, cocoa seeds, peanuts) cucumber plants (pumpkins, cucumbers, melons); fiber plants (cotton, linen, hemp, jute); citrus fruit (oranges, lemons, grapefruit, tangerines); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (water-cate, cinnamon, camphor), or plants such as tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, bananas, and natural rubber plants, as well as ornamentals. The compounds of the formula I are normally used in the form of compositions, and can be applied to the growing area or to the plant to be treated, simultaneously or in succession with other compounds. These additional compounds can be, for example, fertilizers or micronutrient donors or other preparations that influence the growth of plants. They can also be selective herbi-cides, as well as insecticides, fungicides, bactericides, nematocides, molluscicides, or mixtures of several of these preparations, if desired together with other vehicles, surfactants, or application-promoting auxiliaries employed by custom in the art. of the formulation. * '~ * "' The compounds of the formula I can be mixed with other fungicides, resulting in some cases unexpected synergistic activities The mixing components that are particularly preferred are the azoles, such as azaconazole, bitertanol, propi-conazole , difenoconazole, diniconazole, ciproconazole, epoxiconazole, fluquinconazole, flusilazole, flutriazole, hexaconazole, imazalil, imibenconazole, ipconazole, tebuconazole, tetraconazole, fenbucone-zol, metconazole, myclobutanil, perfurazoate, penconazole, bromu-conazole, pirifenox, prochloraz, triadimefon, triadimenol , triflu-mizol, or triticonazole, pyrimidinyl carbinols, such as an ancimidol, fenarimol, or nuarimol, 2-aminopyrimidine, such as bupirimate, dimethirimol, or etirimol, morpholines such as dodemorf, fenpropidin, phenpropimorph, spiroxamine, or tridemorphiminopyrimidines, such as cyprodinil, pyrimethanil, or mepa-nipyrim; pyrrole, such as phenpiclonil or fludioxonil; phenylamide such as benalaxyl; furalaxyl, metalaxyl, R-metalaxyl, ofurace, or oxadixyl; benzimidazoles such as benomyl, carbendazim, debacarb, fuberidazole, or thiabendazole; dicarboximides, such as clozolinate, dichlozoline, iprodine, myclozoline, procymidone, or vinclozoline; carboxamides such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, or tifluzamide; guanidines such as guazatine, dodin, or iminoc-tadine; strobilurins, such as azoxyestrobin, cresoxime-methyl, methominoestrobin, SSF-129 or O-methyl-2-methylester of 2- [. { [(-methyl-3-trifluoromethyl-benzyl) imino] -oxi} -o-tolyl] -glyoxylic; dithiocarbamates such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb, or ziram; N-halothiomethyl-dicarboximides such as captafol, captan, diclofluanid, fluoromide, folpet, or tolifluanid; copper compounds such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancobre, or oxine-copper; nitrophenol derivatives, such as dinocap or nitrotal-isopropyl; organic phosphorus derivatives, such as edifenfos, iprobenfos, isoprotiolano, fosdifeno, pirazofos, or toclofos-methyl; and other compounds of various structures, such as acibenzolar-S-methyl, anilazine, blasticidin-S, quinometionat, chloroneb, chlorothalonil, cymoxanil, diclone, diclomezine, dichlorol, diet-fencarb, dimetomorph, dithianone, etridiazol, fa oxadone, fentin, feriirizona, fluazinam, flusulfamide, fenhexamide, fosetil-alumi-nio, himexazol, casugamicin, metasulfocarb, penicharon, phtali-da, polyoxins, probenazole, propamocarb, pyroquilon, quinoxife-no, quintozene, sulfur, triazoxide, tricyclazole, triforine, or validamycin . Suitable carriers and auxiliaries may be solid or liquid, and are useful substances in the technology of the formulation, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, viscosifiers, binders, or fertilizers. A preferred method for applying a compound of formula I, or an agrochemical composition containing at least one of these compounds, is foliar application. The frequency of application and the concentration of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of the formula I can also penetrate the plant through the roots by means of the soil (systemic action), by flooding the plant site with a liquid formulation, or by applying the compounds in solid form to the plant. the earth, for example, in granular form (application to the earth). In flooded rice crops, these granulates can be applied to the flooded rice field. The compounds of the formula I can also be applied to the seeds (coating) by impregnation of the seeds or tubers, either with a liquid formulation of the fungicide, or by coating them with a solid formulation. The compounds of formula I are used in an unmodified form, or preferably, together with auxiliaries conventionally employed in the formulation art. For this purpose, they are conveniently formulated in a known manner in emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, diluted emulsions, wettable powders, soluble powders, dry powders, granules, and also encapsulations, for example, in polymeric substances. . As with the type of the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating, or watering, are selected in accordance with the intended objectives and the prevailing circumstances. Convenient application concentrations are usually from 5 grams to 2 kilograms of active ingredient (i. a.) per hectare, (ha), preferably from 10 grams to 1 kilogram of active ingredient per hectare, more preferably from 20 grams to 600 grams of active ingredient per hectare. When used as a seed coating agent, convenient dosages are from 10 milligrams to 1 gram of active substance per kilogram of seeds. The formulation, that is, the compositions containing the compound of the formula I, and a solid or liquid auxiliary, is prepared in a known manner, usually by intimate mixing and / or milling the compound with extenders, by example solvents, solid carriers, and optionally surface activity compounds (surfactants). Suitable vehicles and auxiliaries can be solid or liquid, and correspond to the substances ordinarily employed in the technology of the formulation, such as, for example, natural or regenerated mineral substances, solvents, dispersants, wetting agents, viscosifiers, thickeners, binding agents, or fertilizers. These vehicles are described, for example, in International Publication Number WO 97/33890. Other surfactants employed by custom in the art of the formulation are known to the skilled person, or can be found in the pertinent literature. Agrochemical formulations will normally contain from 0.1 to 99 percent by weight, preferably from 0.1 to 95 percent by weight of the compound of formula I, from 99.9 to 1 percent by weight, preferably from 99.8 to 5 percent by weight of a solid or liquid auxiliary, and from 0 to 25 weight percent, preferably from 0.1 to 25 weight percent of a surfactant. Although it is preferred to formulate commercial products as concentrates, the end user will normally use diluted formulations. The compositions may also contain other auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders, or viscosifiers, as well as fertilizers, micronutrient donors, or other formulations to obtain special effects. The following non-limiting Examples illustrate the invention described above in greater detail. Temperatures are given in degrees Celsius. The following abbreviations are used: Et = ethyl; i-propyl = isopropyl; Me = methyl p.f. = melting point. "NMR" means nuclear magnetic resonance spectrum. MS = mass spectrum; "%" is percent weight, unless the corresponding concentrations are indicated in other units.

TT.jgunpl rtg Has Preparer.i? N: Example P-l. Methyl 2-isothiocyanatoothiophen-3-carboxylate In a sulfonation flask, 50.2 grams are added (0.32 moles) of methyl 2-aminothiophen-3-carboxylate to 48 milliliters of chloroform, and 320 milliliters of water. Then s simultaneously add 40.5 grams (0.35 moles) of thiophosgene 1000 milliliters of a saturated aqueous solution of sodium bicarbonate in 40 minutes with stirring. Stirring is continued for 1 hour at room temperature, and then the organic phase is separated. The aqueous phase is extracted twice with chloroform, and the organic phase is dried over sodium sulfate. After removing the chloroform in the water stream under vacuum, 61.3 grams of a dark oil are obtained, which is further purified by column chromatography on silica gel (eluent: ethyl acetate / hexane = 1: 5). 41.5 grams of methyl 2-isothiocyanatothiophene-3-carboxylate are obtained in the form of a chestnut powder having a melting point of 63-65 ° C.

Example P-2. (method 1) 2- (3-thioprop ^ Lureido) thiophen-3 In a sulfonation flask, 13.5 grams (0.023 moles) of n-propylamine are added dropwise to 350 milliliters of tetrahydrofuran and 41.3 grams (0.021 moles) of methyl 2-isothiocyanato-thiophene-3-carboxylate in such a manner that the internal temperature does not rise above 40 ° C. Then the reaction mixture is stirred for 4 hours at reflux temperature, and then the tetrahydrofuran is removed in a stream of water under vacuum. The residue is taken up in ethyl acetate and extracted three times with water. The organic phase is then dried over sodium sulfate, and the solvent is removed in the water stream under vacuum, giving the crude product, which is purified by column chromatography on silica gel (eluent: ethyl acetate / hexane = 1: 3). 32.4 grams of methyl 2- (3-thiopropylureido) -thiophene-3-carboxylate are obtained in the form of a beige powder, having a melting point of 123-126 ° C.

Example P-2. (Method 2) Methyl 2- (3-thiopropylureido) thiophene-3-carboxylate: * In a sulfonation flask, 2.02 grams (0.02 moles) of 1-isothiocyanatopropane are added dropwise to 30 milliliters of dimethyl formamide and 3.0 grams (0.019 moles) of methyl 2-aminothiophen-3-carboxylate. Then the reaction mixture is stirred at 130-135 ° C for 12 hours, and after cooling it is added to 120 milliliters of water. The resulting mixture is then extracted three times with ethyl acetate, and the separated organic phase is dried over sodium sulfate. Then the solvent is removed in a stream of water under vacuum, giving the crude product as a dark oil, which is purified by column chromatography on silica gel (eluent: tert-butyl ether / hexane / = 2: 3). 2.0 grams of methyl 2- (3-thiopropylureido) thiophene-3-carboxylate are obtained in the form of a yellow powder having a melting point of 122-124 ° C.

Example P-3. 3-Butyl-2-thioxo-2,3-dihydro-lH-thieno [2,3-d] pyrimidin-4-one.

In a sulfonation flask, 0.2 grams (0.0049 moles) of a dispersion of about 60 percent sodium hydride are added to 20 milliliters of absolute tetrahydrofuran. Then 1.29 grams (0.0047 moles) of methyl 2- (3-thiobutylureido) thiophene-3-carboxylate, dissolved in 10 milliliters of absolute tetrahydrofuran, are added dropwise, so that the internal temperature remains constant at about 25 ° C. The mixture is stirred at reflux temperature for 3 hours, and then the solvent is removed in a stream of water under vacuum, and the residue is taken up in ethyl acetate / water. After addition of acetic acid, the mixture is extracted three times with ethyl acetate, and the organic phase is dried over sodium sulfate. After removing the solvent in a stream of water under vacuum, 1.06 grams of 3-butyl-2-thioxo-2,3-dihydro-1H-thieno [2,3-d] pyrimidin-4-one are obtained in the form of a chestnut powder that has a melting point of 200-203 ° C.

Example P-4. 2-methylsulfanyl-3-propyl-3H-thieno [2,3-d] pyrimidin-4-one.

In a sulfonation flask, 2.9 grams are added (0.072 moles) of a dispersion of about 60 percent sodium hydride to 50 milliliters of absolute tetrahydrofuran. Then 17.7 grams (0.069 moles) of 2- (3-thiopropylureido) iofen-3-carboxylate f * methyl, dissolved in 100 milliliters of absolute tetrahydrofuran, are added dropwise, so that the internal temperature remains constant at about 25 minutes. ° C. The mixture is stirred at reflux temperature for 5 hours, and after cooling to room temperature, 10.9 grams (0.077 moles) of methyl iodide, dissolved in 10 milliliters of tetrahydrofuran, are added dropwise. The mixture is then stirred for another two hours at the reflux temperature. After the reaction is complete, the tetrahydrofuran is removed in the water stream under vacuum, and the residue is taken up in ethyl acetate. The organic layer is washed twice with water, and then dried over sodium sulfate. After removing the solvent in the water jet under vacuum, the crude product is obtained, which is purified by digestion in normal hexane. 15.1 grams of 2-methylsulfanyl-3-propyl-3H-thieno [2,3-d] pyrimidin-4-one are obtained in the form of a slightly yellowish powder, having a melting point of 94-96 ° C.

Example P-5. 2- (2,2-dichlorocyclopropylmethoxy) -3-propyl normal -3H-thieno [2,3-d] pyrimidin-4-one.

In a sulfonation flask, 2.8 grams (0.02 moles) of 2,2-dichlorocyclopropanmethanol were added to 40 milliliters of absolute tetrahydrofuran, and with stirring, 0 was carefully added. 6 grams (0.015 moles) of a dispersion of NaH. After stirring for one hour at room temperature, a solution of 2.4 grams (0.01 mole) of 2-methylsulfanyl-3-propyl-3H-thieno [2,3-d] pyrimidin-4-one in 20 milliliters of tetrahydrofuran is added, in 2 minutes. After stirring for 4 hours at room temperature, the solvent is removed in a stream of water under vacuum, and the residue is recovered in TBME, and the mixture is repeatedly washed with water. The TBME phase is concentrated in the vacuum water jet, and subsequently the excess of 2,2-dichlorocyclopropylmethanol is distilled in a high vacuum. 3.0 grams of 2- (2,2-dichlorocyclopropyl-methoxy) -3-propyl-3H-thieno [2,3-d] pyrimidin-4-one are obtained in the form of a white powder having a melting point of 64. 66 ° C. Example P-6. 6-Aloro-2- (2,2-dichlorocyclopropylmethoxy) -3-propyl normal-3H-thieno [2,3-d] pyrimidin-4-one. [compound no.3.36] Into a sulfonation flask, 1.3 gram (0.0039 mole) of 2- (2, 2-dichlorocyclopropylmethoxy) -3-propyl-3H-thieno [2,3-d] pyrimidin-4-one are added, with stirring, to 15 milliliters of pyridine. Absolute Then the internal temperature rises 70 ° C, and then 0.78 grams (0.0059 moles) of N-chlorosuccinimide (NCS) are added for about 5 minutes in small portions. After stirring for 2 hours at 70-75 ° C, the pyridine is removed in a stream of water under vacuum. The crude product thus obtained is purified by column chromatography on silica gel (eluent: normal hexane / ethyl acetate = 4: 1), yielding 0.55 grams of 6-chloro-2- (2,2-dichlorocyclopropylmethoxy) -3-propyl. -3H-Thieno [2,3-d] pyrimidin-4-one in the form of a beige powder having a melting point of 94-96 ° C.

Table 1 comp. Hi «2 H3 K, H5 He H7 Re data Physical No. p.f. ° C 1. 1 6-CI H Me Me HHHH 1.2 6-Br H Me Me HHHH 1.3 H 7-Cl Me Me HHHH 1.4 6-Cl H Et Me HHHH 1.5 6-Br H Et Me HHHH 1.6 6-CI H n-propyl Me HHHH 1.7 6-Br H n-propyl Me HHHH 81-85 1. 8 H 7-Br n-propyl Me H H H H 1.9 6-CI H n -butyl Me H H H H'-h-1.10 6-Br H n -butyl Me H H. H H 66-69 .11 H 7-CI n -butyl Me H H H H .12 6-CI H i -buyl Me H H H H .13 6-Br H i -butyl Me H H H H .14 6-CI H cyclo- Me H H H H propyl. '-CH2 .15 6-Br H cyclo- Me HHHH 77-80 propyl-CH2 .16 6-Ci H Me H Me HHH .17 6-Br H Me H Me HHH .18 H 7-CI Me H Me HHH. 19 6-CI H Et H Me HHH .20 6-Br H Et H Me HHH .21 6-CI H n-propyl H Me HHH 1.22 6-Br H n-propyl H Me HHH 49-51 1. 23 7-Br H n-propyl H Me H H H 1.24 6-CI H n-butyl H Me H H H 1.25 6-Br H n -butyl H Me H H H 68-72 1. 26 H 7-CI n-buyl H Me HHH 1.27 6-CI H i -butyl H Me HHH 1.28 6-Br H -butyl H Me HHH 1.29 6-CI H cyclo- H Me HHH propyl. -CH2 1.30 6 -Br H cycle- H Me HHH 78-81 pro il -CH2 1.31 6-CI H Me HC! Cl HH 1.32 6-Br H Me H Cl Cl HH 1.33 H 7-CI Me H Cl Cl HH 1.34 6-CI H Et H Cl Cl HH 1.35 6-Br H Et H Cl Cl HH 1.36 6-CI H n-propyl H Cl Cl HH 1.37 6-Br H n-propyl H Cl Cl HH oil 1H-RMI \ l 1. 38 7-Br H n "propyl H Cl Cl HH 1.39 6-CI H n-butyl H Cl Cl HH .1.40 6-Br H n -butyl H Cl Cl HH 1.41 H 7-CI n-butyl H Cl Cl HH 1.42 6-CI H i -butyl H Cl Cl HH 1.43 6-Br H μbutyl H Cl Cl HH 1.44 6-CI H • cyclo- H Cl Cl HH propyl -CH2 1.45 6-Br H cyclo- H Cl Cl HH propi -CH2 1.46 6-CI H Me HFFHH 1.47 6-Br H Me HFFHH 1.48 H 7-CI Me HFFHH 1.49 6-C! H Et H 'FFHH 1.50 6-Br H Et HFFHH 1. 51 6-CI H n "propyl H F F H H 1. 52 6-Br H n-propyl H F F H H 1. 53 7-Br H n-propyl H F F H H 1. 54 6-CI H n-butyl H F F H H 1. 55 6-Br H n.butyl H F F H H 1. 56 H 7-CI n-butyl H F F H H 1. 57 6-CI H > - butyl H F F H H 1. 58 6-Br H i -butyl H F F H H 1. 59 6-CI H cycle- H F F H H propyl-CH2 1.60 6-Br H cyclo- H F F H H propyl -CH2 1.61 6-CI H n'propyl H Me Me H H 1. 62 6-Br H n-propyl H Me Me H H 1. 63 6-CI H n-butyl H Me Me H H 1. 64 6-Br H n-butyl H Me Me H H 1. 65 6-CI H n.propyl H Me H Me H 1. 66 6-Br H n.propyl H Me H Me, 5 1. 67 6-CI H n-butyl H Me H Me H 1. 68 6-Br H n-butyl H Me H Me H comp. Ri R2 R Rs Re Rr Re Physical data No. 2. 25 6-CI H n-butyl H Cl Cl H 2. 26 6-Br H n-butyl H Cl Cl H H 2. 27 6-CJ H i -butyl H Cl Cl H H 2. 28 6-Br H - - / butyl H Cl Cl H H 2. 29 6-CI H cycle- H Cl Cl H H propyl -CH 2 2.30 6-Br H cyclo- H Cl Cl H H propyl '-CH2 2.31 6-CI H Me H F F H H 2. 32 6-Br H Me H F F H H 2. 33 6-Br H Et H F F H H 2. 34 6-Br H n-propyl H F F H H 2. 35 6-CI H n-butyl H F F H H 2. 36 6-Br H n-butyl H F F H H 2. 37 6-CI H i -butyl H F F H H 2. 38 6-Br H i -butyl H F F H H 2. 39 6-CI H H H cyclo-H F F propyl > -CH- 2 2.40 6-Br H cyclo- H F F H H propyl '-CH2 2.41 6-CI H Me H Me Me H H 2. 42 6-Br H Me H Me Me H H 2. 43 6-Br H Et H Me Me H H 2. 44 6-Br • H n-propyl H Me Me H H 2. 45 6-Br H n-'butyl H Me Me H H 2. 46 6-Br H Et H H H H H 2. 47 6-Br H n-propyl H Me H Me H 2.48 6-Br H "'butyl H Me H Me H 2.49 6-Br H n-propyl H CF3 H H H 2.50 6-Br H n-; butyl H CF3 H H H Table_3. comp. Ri R3 4 R «Rr Re data Physical numbers p.f. ° C 3. 1 6-CI H Me Me HHHH 3.2 6-Br H Me Me HHHH 3.3 6-1 H Me Me HHH * H * * * * 3.4 6-CI H Et Me HHHH 3.5 6-Br H Et Me HHHH 3.6 6-CI H n-propyl Me HHHH 73-77 3. 7 6-Br H n-propyl Me H H H H 113-116 3. 8 6-1 H n-propyl Me HHHH 3.9 6-CI H n -butyl Me HHHH 3.10 6-Br H n -butyl Me HHHH 3.11 6-1 HH n.butyl Me HHHH 3.12 6-CI HH -butyl Me HHHH 3.13 6-Br H i -butyl Me HHHH 3.14 6-CI H cyclo- Me HHHH propyl -C? 2 3.15 6-Br H cyclo- Me HHHH propyl -CH2 3.16 6-CI H Me H Me HHH 3.17 6-Br H Me H Me HHH 3.18 6-IH Me H Me HHH 3.19 6-CI H Et H Me HHH 3.20 6-Br H Et H Me HHH 3.21 6-Ci H p "propyl H Me HHH 66-68 3. 22 6-Br H n-propyl H Me H H H 64-66 3. 23 6-I H n-propyl H Me H H H 3.24 6-CI H n -butyl H Me H H H 3.25 6-Br H n. butyl H Me H H H 3.26 6-I H n. butyl H Me HHH 3.27 6-CI H -butyl H Me HHH 3.28 6-Br H i -butyl H Me HHH 3.29 6-CI H cyclo- H Me HHH propyl -CH2 3.30 6-Br H cyclo- H Me HHH propyl < -CH2 3.31 6-CI H Me H Cl Cl HH 3.32 6-Br H Me H Cl Cl HH 3.33 6-1 H Me H Cl Cl H H. ^ 3.34 6-CI H Et H Cl Cl HH 3.35 6-Br H Et H Cl Cl HH 3.36 6-CI H n-propyl H Cl Cl HH 94-96 3. 37 6-Br H n-propyl H Cl Cl HH 3.38 6-1 H n-propyl H Cl Cl HH 3.39 6-CI H n-butyl H Cl Cl HH 3.40 6-Br H n -butyl H Cl Cl HH 3.41 6 -1 H n -butyl H Cl Cl HH - 3.42 6-CI H i -butyl H Cl Cl HH 3.43 6-Br H i -butyl H Cl Cl HH 3.44 6-CI H cyclo- H Cl Cl HH propyl -CH2 3.45 6-Br H cycle- H Cl Cl HH propi -CH2 3.46 6-CI H Me HFFHH 3.47 6-Br H Me HFFHH 3.48 6-IH Me HFFHH 3.49 6-CI H Et HFFHH 3.50 6-Br H Et HFFHH 3.51 6- CI H n-propyl HFFHH Oil 1H-RMW 3. 52 6-Br H n-propyl H F F H H Oil 1 H-NMR. 3. 53 6-IH n "propyl HFFHH 3.54 6-CI n n -butyl HFFHH 3.55 6-Br H n -butyl HFFHH 3.56 6-IH n-butyl HFFHH 3.57 6-Ci H i -butyl HFFHH 3.58 6-Br H - butyl HFFHH 3.59 6-CI H cyclo-HFFHH propyl-CH2 3.60 6-Br H cyclo-HFFHH propyl. -CH2 * t 3.61 6-CI H n "propyl H Me Me HH" 3.62 6-Br H n-propyl H Me Me HH 3.63 6-CI H n -butyl H Me Me HH 3.64 6-Br H n -butyl H Me Me HH 3.65 6-CI H n.propyl H Me H Me H 3.66 6-Br H Nipropyl H Me H Me H 3.67 6-CI H n-butyl H Me H Me H 3.68 6-Br H n-butyl H Me H Me H 3.69 6-Br H n-propyl H CF3 HH 4. 24 H 6-CI n-butyl H Me HHH 4.25 H 6-Br n-butyl H Me HHH 4.26 7-Br H n-butyl H Me HHH 4.27 H 6-CI -butyl H Me HHH 4.28 7-Br H i -butyl H Me HHH 4.29 H 6-CI cyclo- H Me HHH propyl -CH2 4.30 7-Br H cyclo- H Me HHH propyl -CH2 4.31 H 6-CI Me H Cl Cl HH 4.32 H 6-Br Me H Cl Cl HH 4.33 7-Br H Me H Cl Cl HH 4.34 H 6-CI Et H Cl Cl HH • 4. 35 7-Br H Et H Cl Cl H H 4.36 H 6-CI n-propyl H Cl Cl HH 4.37 H 6-Br n-propyl H Cl Cl HH 4.38 7-Br H n-propyl H Cl Cl HH 4.39 H 6- CI n-butyl H Cl Cl HH 4.40. H 6-Br n -butyl H Cl Cl H H 4.41 7-Br H n. butyl H Cl Cl HH 4.42 H 6-CI -butyl H Cl Cl HH 4.43 7-Br H i -butyl H Cl Cl HH 4.44 H 6-CI cycli- H Cl Cl HH propyl -CH ^ 4.45 7-Br H cycle - H Cl Cl HH propyl ^ CH2 4.46 H 6-CI Me HFFHH 4.47 H 6-Br Me HFFHH 4.48 7-Br H Me HFFHH 4.49 H 6-CI Et HFFHH 4.50 7-Br H Et HFFHH 4.51 H 6-CI n- propyl HFFHH 4.52 H 6-Br n-propyl HFFHH 4.53 7-Br H. n-propyl HFFHH 4.54 H 6-CI n-butyl HFFHH 4.55 H 6-Br n-but; or HFFHH 4.56 7-Br H n-butyl HFFHH 4.57 H 6-CI i-butyl HFFHH 4.58 7-Br H i- butyl HFFHH 4.59 H 6-CI cycle HFFHH propyl-CH2 4.60 7-Br H cyclo- HFFHH propyl-CH2 4.61 H 6-CI n-propyl H Me Me HH 4.62 7-Br H n-propyl H Me Me HH 4.63 H 6 -CI n-butyl H Me Me HH 4.64 7-Br H n -butyl H Me Me HH 4.65 H. 6-CI n-propyl H Me H Me. , H 4.66 7-Br H n-propyl H Me H Me H 4.67 H 6-CI n-butyl H Me H Me H 4.68 7-Br H n-butyl H Me H Me H 4.69 H 6-CI n-propyl H CF3 HHH 4.70 7-Br H n-propyl H CF3 HHH Examples for the specific combination of formulations are as disclosed, for example, in International Publication Number WO 97/33890, for example for wettable powders, emulsifiable concentrates, dry powders, extruder granules, coated granules, solutions, and concentrated in suspension.

Biological Examples: Fungicide Actions Bl: Action against Puccinia graminis in wheat a) _ Residual protective action 6 days after sowing, the wheat plants are sprayed to the point of dripping with a mixture of aqueous spray (0.02% active ingredient) prepared from a Wettable powder formulation of the test compound, and are infected 24 hours later with an uredospore suspension of the fungus. After an incubation time of 48 hours (conditions: 95 to 100 percent relative humidity at 20 ° C), the plants are left at 22 ° C in a greenhouse. The evaluation of the fungal infestation is done 12 days after the infection? »• - Systemic action Wheat plants are watered 5 days after sowing with an aqueous spray mixture (0.006 percent active ingredient, based on the volume of the soil), prepared from a wettable powder formulation of the test compound . Care is taken that the spray mixture does not come into contact with the growing parts of the plants. After 48 hours, the plants are infected with a suspension of uredospores of the fungus. After an incubation period of 48 hours (conditions: 95 to 100 percent relative humidity at 20 ° C), the plants are left at 22 ° C in a greenhouse. The evaluation of the fungal infestation is done 12 days after the infection. The compounds of Tables 1-4 show good to excellent activity, preferably compounds 1.7, 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, 3.36, 3.51, 3.52, 4.8 and 4.23.

Example B-2: Action against Colletotrichum lagenari? in cucumbers After a cultivation period of 2 weeks, the cucumber plants are sprayed with an aqueous spray mixture (0.002% concentration) prepared from a wettable powder formulation of the test compound, and infected 2 days later with a spore suspension (1.5 x 10 5 spores / milliliter) of the fungus, and incubated for 36 hours at 23 ° C and with high humidity, then the incubation is continued with normal humidity and at approximately 22 ° C. The evaluation of the fungal infestation is made 8 days after the infection The compounds of Tables 1-4 they show a good to excellent activation, of preferences the compounds 1.7, 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, 3.36, 3.51, 3.52, 4.8 and 4.23.

Example B-3 Residual protective action against Venturia inaequalis in apples. Apple clippings with fresh shoots 10 to 20 centimeters long are sprayed to the point of dripping with a spray mixture (0.02% active ingredient) prepared from a wettable powder formulation of the test compound. The plants are infected 24 hours later with a suspension of conidia of the fungus. Then the plants are incubated for 5 days with 90 to 100 percent relative humidity, and left in a greenhouse for another 10 days at 20 ° C to 24 ° C. The evaluation of the fungal infestation is done 12 days after the infection. The compounds of Tables 1-4 show a good activity, preferably compounds 1.7 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, 3.36, "§ > • .51-, 3.52 , 4.8 and 4.23.

Example B-4: Action against Erysiphe gramínis in barley a) Residual protective action Barley plants approximately 8 centimeters high, are sprayed to the point of dripping with a spray mixture (0.02 percent active ingredient) prepared from a wettable powder formulation of the test compound, and the treated plants are sprinkled with conidia of the fungus 3 to 4 hours later. The infected plants are left in a greenhouse at 22 ° C. The evaluation of the fungal infection is done 12 days after the infection. b) Systemic action Barley plants about 8 centimeters high, are irrigated with an aqueous spray mixture (0.002 percent active ingredient, based on the volume of the soil) prepared from a wettable powder formulation. of the test compound. Care is taken that the spray mixture does not come into contact with the growing parts of the plants. The treated plants are sprinkled 48 hours later with conidia of the fungus. The infected plants are then left in a greenhouse at 22 ° C. The evaluation of the fungal infestation is done 12 days after the infection. Compared with the control plants, the infestation of the plants treated with the compounds of the formula I, for example the compounds 1.7 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, and 3.36, is of 20 percent or less.

Example B-5: Action against Podosphaera Iß cotricha in apple shoots. Apple clippings with fresh buds about 15 centimeters long are sprayed with a spray mixture (0.06 percent active ingredient). The plants are infected 24 hours later with a suspension of conidia of the fungus, and are left in a climatic chamber with 70 percent relative humidity, and at 20 ° C. The evaluation of the fungal infestation is done 12 days after the infection. The compounds of Tables 1-4 show good activity. The following compounds exhibit an especially strong efficacy: 1.7 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, and 3.36, (0 to 5 percent infestation).

Example B-6; Action against üncin the necator on vines The 5-week-old vine clippings are sprayed with a spray mixture (200 ppm active ingredient) prepared from a wettable powder formulation of the test compound. The plants are infected 24 hours later with conidia of strongly infested vine leaves, and are shaken on the test plants. Then the plants are incubated at 26 ° C and with 60 percent relative humidity. The evaluation of the fungal infestation is made approximately 14 days after the infection. Compared with the control plants, the infestation of the plants treated with the compounds of the formula I, for example the compounds 1.7 1.10, 1.15, 1.22, 1.25, 1.30, 1.37, 3.6, 3.7, 3.21, 3.22, and 3.36, is of 20 percent or less.

Claims (16)

1. A compound of the formula I: wherein: A is phenyl, thienyl (including the 3 isomers), thiazolyl, or pyridyl; X is oxygen or sulfur; x is hydrogen, halogen, or trimethylsilyl, - R2 is hydrogen, halogen, or trimethylsilyl, - at least one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, - (CH 2) "-cycloalkyl of 3 to 8 carbon atoms which are unsubstituted or substituted by halogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; alkoxygen of 1 to 4 carbon atoms-alkenyl of 2 to 6 carbon atoms; alkoxy of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkenyl of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkenyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkynyl of 2 to 6 carbon atoms; - (CH2) n-alkoxy of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) n-thioalkyl of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) n-monoalkyl of 1 to 4 carbon atoms-aminocycloalkyl of 3 to 6 carbon atoms; or N = CR9R? 0; n is 1, 2, 3, or 4; R4, R5, Rd, R7 and Rs are each independently of the others, hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or halogen, wherein at least one of the substituents R4- R8 must be different from hydrogen; and R9 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 atoms of carbon, "haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; Rio is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 carbon atoms. carbon, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; and at least one of Rg and Rio is not hydrogen.
2. 2. A compound of the formula I according to claim 1, wherein: A is thienyl, and X is oxygen.
3. 3. A compound of the formula I according to claim 2, wherein: Ri is hydrogen, fluorine, chlorine, bromine, or iodine; R2 is hydrogen, fluorine, chlorine, bromine, or iodine; at least one of Ri and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, haloalkenyl of 2 to 4 carbon atoms, haloalkynyl of 2 to 4 carbon atoms, or CH2-cycloalkyl of 3 to 4 carbon atoms, which are unsubstituted or substituted by halogen, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms; , R5, Re, R7 and Re are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 4 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen. 4. A compound of the formula I, according to claim 3, wherein: R3 is alkyl of 1 to 4 carbon atoms, alkenyl of 2 to 4 carbon atoms, alkynyl of 2 to 4 carbon atoms, each of which is unsubstituted or substituted by chlorine or bromine; or -CH2-cycloalkyl of 3 to 6 carbon atoms, which is unsubstituted or substituted by fluorine, chlorine, bromine, or iodine; R, R5, Re, R7, and Rs are each independently of the others, hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1 to
4. 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents Rs-Rs must be different from hydrogen.
5. 5. A compound of the formula I according to claim 4, wherein: Ri is hydrogen, chlorine, or bromine; R2 is hydrogen, chlorine, or bromine; at least one of Ri and R2 is not hydrogen; R3 is alkyl of 1 to 4 carbon atoms or CH2-cyclopropyl; R, R5, Re, R7, and Rs are each independently of the others, hydrogen, chlorine, bromine, iodine, alkyl of 1 to 4 carbon atoms, or haloalkyl of 1 to 2 carbon atoms, wherein at least one of the substituents R4-R8 must be different from hydrogen.
6. 6. A compound of formula I according to claim 5, wherein: A is thienyl [2.3-d], R3 is alkyl of 3 to 4 carbon atoms, R4, R5, R6, R7 and Re are each independently of the others, hydrogen, chlorine, bromine, methyl, or CF3, wherein at least one of the substituents R4-R8 must be different from hydrogen.
7. 7. A compound of the formula I according to claim 5, wherein: A is thienyl [3.2-d]; R3 is alkyl of 3 to 4 carbon atoms; R4, R5, Re, R7, and Re are each independently of the others, hydrogen, chlorine, bromine, methyl, or CF3, wherein at least one of the substituents R4-Rs must be different from hydrogen.
8. 8. A compound of the formula I according to claim 1 wherein: A is phenyl and X is oxygen.
9. 9. A compound of the formula I according to claim 1, wherein: A is pyridyl and X is oxygen.
10. 10. A compound according to claim 1, selected from: 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-propyl-3H-quinazolin-4-one, 6-bromo-2- (2-methylcyclopropylmethoxy) ) -3-n-propyl-3H-quinazolin-4-one, 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-butyl-3H-quinazolin-4-one, 6-bromo-2- (2 -methylcyclopropylmethoxy) -3-n-butyl-3H-quinazolin-4-one, 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2,3 -d] pyrimidin-4-one, 6-chloro-2- (1-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2,3-d] pyrimidin-4-one, • -; > - 6-bromo-2- (2-methylcyclopropylmethoxy) -3-n-propyl-3H-thieno [2,3-d] pyrimidin-4-one, 6-chloro-2- (2-methylcyclopropylmethoxy) -3-n-propyl -3H-Thieno [2,3-d] pyrimidin-4-one, 6-bromo-2- (1-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one, 6-chloro -2- (1-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one, 6-bromo-2- (2-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one, 6-chloro-2- (2-methylcyclopropylmethoxy) -3-n-butyl-3H-thieno [2,3-d] pyrimidin-4-one.
11. 11. A composition for controlling and preventing pests, wherein the active ingredient is a compound as claimed in claim 1, together with a suitable vehicle.
12. 12. The use of a compound of formula I according to claim 1, to protect plants against infestation by phytopathogenic microorganisms.
13. 13. A method for controlling or preventing infestation of plants grown by phytopathogenic microorganisms, by applying a compound of the formula I as claimed in claim 1 to the plants, to the parts thereof, or to the place of the same.
14. 14. A method according to claim 13, wherein the phytopathogenic microorganism is a fungal organism.
15. 15. A method for the preparation of a compound of the formula I according to claim 1 which comprises .- a) converting an -aminocarboalkoxyheterocycle of the formula II, wherein Rx and R2 have the meanings mentioned. for the formula I-, and R is alkyl of 1 to 6 carbon atoms, with thiophosgene in an alkaline medium, and in the presence of a solvent, in an isothiocyanate of formula III: b) treating the isothiocyanate with an amine of the formula wherein R3 has the meaning mentioned for formula I, in the presence of a solvent, and if necessary in the presence of a base, and obtaining, with closure and ring, the 2-thioxopyrimidin-4-one derivative of the formula V: c) treating the amine of the formula II with a 1-isocyanatoalkane in the presence of a solvent (alcohol or dimethylformamide), obtaining thioureidothiophenes of the formula IV: IV
16. 16. A compound of formula IV: IV wherein: A is thienyl [2,3-d] or thienyl [3.2-d]; Ri is hydrogen, halogen, or trimethylsilyl; R2 is hydrogen, halogen, or trimethylsilyl; and at least one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl from 2 to 6 carbon atoms, or CH2-cycloalkyl of 3 to 8 carbon atoms, which are unsubstituted or substituted by halogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; R4, Rs, R <r> R, and Re are each independently of the others, hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or halogen, wherein at least one of the substituents R4- R8 must be different from hydrogen; and R is hydrogen or alkyl of 1 to 6 carbon atoms. SUMMARY Novel derivatives of pyrimidin-4-one and pyrimidin-4-thione of the formula I: wherein: A is phenyl, thienyl (including the 3 isomers), thiazolyl, or pyridyl; X is oxygen or sulfur; R x is hydrogen, halogen, or trimethylsilyl; R2 is hydrogen, halogen, or trimethylsilyl; at least one of Rx and R2 is not hydrogen; R3 is alkyl of 1 to 6 carbon atoms, haloalkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, haloalkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, haloalkynyl of 2 to 6 carbon atoms, - (CH 2) n-cycloalkyl of 3 to 8 carbon atoms which are unsubstituted or substituted by halogen, alkyl of 1 to 6 carbon atoms, or haloalkyl of 1 to 6 carbon atoms; alkoxy of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; al-coxyl of 1 to 4 carbon atoms-alkenyl of 2 to 6 carbon atoms; alkoxy of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkyl of 1 to 6 carbon atoms; thioalkyl of 1 to 4 carbon-non-alkenyl atoms of 2 to 6 carbon atoms; thioalkyl of 1 to 4 carbon atoms-alkynyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkyl of 1 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkenyl of 2 to 6 carbon atoms; monoalkyl of 1 to 4 carbon atoms-aminoalkynyl of 2 to 6 carbon atoms; - (CH2) n-alkoxy of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) "- thioalkyl of 1 to 4 carbon atoms-cycloalkyl of 3 to 6 carbon atoms; - (CH2) n-monoalkyl of 1 to 4 carbon atoms-to inocicloalkyl of 3 to 6 carbon atoms; or N = CR9R? 0; n is 1, 2, 3, or 4; R4, R5, Re, 7 and s are each independently of the others, hydrogen, alkyl of 1 to 4 carbon atoms, haloalkyl of 1 to 4 carbon atoms, or halogen, wherein at least one of the substituents R4- 8 it must be different from hydrogen; and R9 is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 atoms carbon, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms 1, or haloalkoxy of 1 to 6 carbon atoms; Rio is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, pyridyl, furyl, thienyl, or phenyl which is unsubstituted or mono- to penta-substituted by halogen, alkyl of 1 to 6 carbon atoms. carbon, haloalkyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or haloalkoxy of 1 to 6 carbon atoms; and at least one of Rg and Rio is not hydrogen. The novel compounds have protective properties of plants, and are suitable for protecting plants against infestation by phytopathogenic microorganisms, in particular fungi. * * * * *