Pyrrolecarboxamides and pyrrolethioamides as fungicides

Abstract

Novel pyrrole derivatives of formula (I) wherein X is oxygen or sulfur; R1 is C1-C4alkyl unsubstituted or substituted, with the exception of CF3; C3-C6cycloalkyl unsubstituted or substituted; or halogen; R2 is hydrogen, C1-C4alkyl unsubstituted or substituted, C1-C4alkoxy unsubstituted or substituted, cyano or halogen; R3 is C1-C4alkyl unsubstituted or substituted; and A is orthosubstituted aryl; orthosubstituted heteroaryl; bicycloaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted. The novel compounds have plant-protective properties and are suitable for protecting plants against infestations by phytopathogenic microorganisms.

Description

[0001] The present invention relates to novel substituted pyrrolecarboxamides or pyrrolethioamides which have microbicidal activity, in particular fungicidal activity. The invention also relates to the preparation of these substances, to agrochemical compositions which comprise at least one of the novel compounds as active ingredient, to the preparation of the compositions mentioned and to the use of the active ingredients or compositions in agriculture and horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

[0002] The pyrrolecarboxamides (thioamides) of the present invention have the general formula I 1

[0003] wherein

[0004] X is oxygen or sulfur;

[0005] R1 is C1-C4alkyl unsubstituted or substituted, with the exception of CF3; C3-C6cycloalkyl unsubstituted or substituted; or halogen;

[0006] R2 is hydrogen, C1-C4alkyl unsubstituted or substituted, C1-C4alkoxy unsubstituted or substituted, cyano or halogen;

[0007] R3 is C1-C4alkyl unsubstituted or substituted; and

[0008] A is orthosubstituted aryl; orthosubstituted heteroaryl; bicycloaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted.

[0009] Surprisingly, it has now been found that the compounds of formula (I) exhibit improved biological properties which render them more suitable for the practical use in agriculture and horticulture.

[0010] Where asymmetrical carbon atoms are present in the compounds of formula 1, these compounds are in optically active form. The invention relates to the pure isomers, such as enantiomers and diastereomers, as well as to all possible mixtures of isomers, e.g. mixtures of diastereomers, racemates or mixture of racemates.

[0011] Within the present specification alkyl denotes methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl. Non-branched alkyl is preferred. Alkyl as part of other radicals such as alkoxy, haloalkyl, alkylcycloalkyl, alkylcycloalkoxy, etc. is understood in an analogous way. Halogen will be understood generally as meaning fluoro, chloro, bromo or iodo. Fluoro, chloro or bromo are preferred meanings. Halogen as part of other radicals such as haloalkyl, haloalkoxy, haloalkenyl, haloalkenyloxy, haloaryl or haloheteroaryl, etc. is understood in an analogous way. Haloaryl or haloheteroaryl designates mono- to five times halo-substituted aryl, whereby the halogens are independently chosen. Where more than two halogens are present, the halogens are preferably the same, e.g. trifluorophenyl, trichlorophenyl, tetrachlorophenyl or perchlorophenyl.

[0012] Haloalkyl is a monohalogenated to perhalogenated alkyl radical, such as, inter alia, fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl.

[0013] Haloalkoxy is a monohalogenated to perhalogenated alkoxy radical, such as, inter alia, OCH2F, OCHF2, OCF3, OCHFCH3, OCH2CH2Br, OCF2CHFCl.

[0014] Substituted alkyl will be understood as for example haloalkyl, alkoxy-alkyl, haloalkoxy-alkyl.

[0015] Cycloalkyl is, depending on the ring size, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Substituted cycloalkyl will be understood for example as alkyl-cycloalkyl, haloalkyl-cycloalkyl, alkoxy-cycloalkyl, haloalkoxy-cycloalkyl, halo-cycloalkyl, alkoxyalkyl-cycloalkyl, haloalkoxyalkyl-cycloalkyl.

[0016] Alkenyl will be understood as meaning straight-chain or branched alkenyl such as allyl, methallyl, 1-methylvinyl or but-2-en1-yl. Preferred alkenyl radicals contain 3 to 4 carbon atoms in the chain.

[0017] Alkynyl can likewise, in accordance with the number of carbon atoms, be straight-chain or branched and is typically propargyl, but-1-yn-1-yl or but-1-yn-3yl.

[0018] Aryl is phenyl or naphthyl.

[0019] Heteroaryl will be understood as a 5- to 10 membered ring that may contain up to 3 heteroatoms, such as nitrogen, oxygen or sulfur. The following list of examples is not exhaustive: furyl, thienyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrrolyl, dithiolyl, oxathiolyl, dioxazolyl, oxathiazolyl, oxathiolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, naphthyridinyl, isobenzofuranyl, isoindolyl, benzothiadiazolyl, benzisoxazolyl, benzothienyl, purinyl, 5,6-dihydro-1,4,2-dioxazinyl, and the like.

[0020] Bicycloaryl or bicycloheteroaryl will be understood as a 6-membered aryl or 6-membered heteroaryl ring, wherein it may contain up to 3 heteroatoms such as nitrogen, oxygen or sulfur, and which is fused to an additional ring. The fused ring may be aromatic, partially hydrogenated or completely saturated and may be a ring from 5 to 7 ring members, of which up to 3 members may be heteroatoms selected from he group nitrogen, oxygen and sulfur. The following list of examples is not exhaustive: dihydroisobenzofuranyl, dihydroisoindolyl and the like.

[0021] Substituted aryl, substituted heteroaryl, substituted bicycloaryl or substituted bicycloheteroaryl will be understood as substituted by, inter alia, cycloalkyl, cycloalkenyl, cycloalkadienyl, phenyl, heteroaryl, cyano, nitro, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyl, haloalkoxyalkyl, alkenyl, alkynyl.

[0022] Preferred embodiment of compounds of formula I are those wherein

[0023] X is oxygen or sulfur; or

[0024] X is oxygen; or

[0025] X is sulfur; or

[0026] R1 is C1-C4alkyl unsubstituted or substituted, with the exeption of CF3; C3-C6cycloalkyl unsubstituted or substitited; or halogen; or

[0027] R1 is C1-C4alkyl; C1-C4haloalkyl; C1-C4alkoxy-C1-C4alkyl; C1-C4haloalkoxy-C1-C4alkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl or halogen; or halogen; or

[0028] R1 is C1-C3alkyl; C1-C3haloalkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C3alkyl, C1-C3haloalkyl or halogen; or

[0029] R1 is C1-C2alkyl, C1-C3haloalkyl or cyclopropyl; or

[0030] R1 is methyl, ethyl, CFH2 or CF2H; or

[0031] R2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, cyano or halogen; or

[0032] R2 is hydrogen, C1-C4alkyl or C1-C4haloalkyl; or

[0033] R2 is hydrogen or C1-C3alkyl; or

[0034] R2 is hydrogen; or

[0035] R3 is C1-C4alkyl unsubstituted or substituted; or

[0036] R3 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl or C1-C4haloalkoxy-C1-C4alkyl; or

[0037] R3 is C1-C4alkyl, C1-C3haloalkyl or C1-C3alkoxy-C1-C3alkyl; or

[0038] R3 is C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl; or

[0039] R3 is methyl or CH2OCH3; or

[0040] A is orthosubstituted aryl; orthosubstituted heteroaryl; bicycloaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted; or

[0041] A is a group 2345

[0042] or

[0043] A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31, A32A or A33; or

[0044] A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27, A31 or A33; or

[0045] A is A31 or A33; or

[0046] R4 is C3-C7cycloalkyl, C4-C7cycloalkenyl, C5-C7cycloalkadienyl wherein the cycloalkyl group can be mono- to pentasubstituted by halogen, hydroxy, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C4alkenyl, C2-C5alkynyl, C1-C4haloalkyl; phenyl unsubstituted or substituted by halogen, nitro, cyano, CHO, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C5alkenyl, C2-C5alkynyl, C1-C4haloalkyl, COOC1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-C1-C4alkoxy, C1-C4haloalkoxy-C1-C4alkyl, C1-C4haloalkyl-C1-C4alkoxy; thienyl, furyl, pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, imidazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C6haloalkyl, C1-C6alkyl, C2-C5alkenyl, C2-C5alkynyl, nitro, cyano, hydroxy, CHO, C1-C6alkoxy, COOC1-C6alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl or C1-C6haloalkoxy; or

[0047] R4 is C5-C7cycloalkyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cycloalkenyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cycloalkadienyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C4alkenyl, C2-C4alkynyl or C1-C4haloalkyl; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy or C1-C4haloalkyl; thienyl, furyl, oxazolyl, isoxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4haloalkyl, C1-C4alkyl, hydroxy, C1-C4alkoxy or C1-C4haloalkoxy; or

[0048] R4 is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C1-C2alkyl, C1-C2haloalkyl or C1-C2haloalkoxy; thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4haloalkoxy; or

[0049] R4 is phenyl substituted by halogen; C5-C7cycloalkyl; or halothienyl; or

[0050] R5 is hydrogen, cyano, nitro, halogen, C1-C4haloalkyl, C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy; or

[0051] R5 is hydrogen, halogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy; or

[0052] R5 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy or C1-C3haloalkoxy; or

[0053] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, halogen, C1-C4haloalkyl, C1-C4alkyl, C2-C5alkenyl, C2-C5alkynyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C6haloalkoxy-C1-C4alkyl, C1-C4haloalkoxy or C3-C7cycloalkyl; or

[0054] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; or

[0055] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen or C1-C3alkyl.

[0056] Within the group of compounds of formula I those compounds are preferred wherein:

[0057] R1 is C1-C4alkyl; C1-C4haloalkyl; C1-C4alkoxy-C1-C4alkyl; C1-C4haloalkoxy-C1-C4alkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl or halogen; or halogen;

[0058] R2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, cyano or halogen;

[0059] R3 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl or C1-C4haloalkoxy-C1-C4alkyl;

[0060] A is a group 6789

[0061] and

[0062] R4 is C3-C7cycloalkyl, C4-C7cycloalkenyl, C5-C7cycloalkadienyl wherein the cycloalkyl group can be mono- to pentasubstituted by halogen, hydroxy, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C4alkenyl, C2-C5alkynyl, C1-C4haloalkyl; phenyl unsubstituted or substituted by halogen, nitro, cyano, CHO, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C5alkenyl, C2-C5alkynyl, C1-C4haloalkyl, COOC1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-C1-C4alkoxy, C1-C4haloalkoxy-C1-C4alkyl, C1-C4haloalkyl-C1-C4alkoxy; thienyl, furyl, pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, imidazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C6haloalkyl, C1-C6alkyl, C2-C5alkenyl, C2-C5alkynyl, nitro, cyano, hydroxy, CHO, C1-C6alkoxy, COOC1-C6alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl-or C1-C6haloalkoxy;

[0063] R5 is hydrogen, cyano, nitro, halogen, C1-C4haloalkyl, C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy;

[0064] R6, R7, R6, R9 and R10 are identical or different and are each independently of the others hydrogen, halogen, C1-C4haloalkyl, C1-C4alkyl, C2-C5alkenyl, C2-C5alkynyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C6haloalkoxy-C1-C4alkyl, C1-C4haloalkoxy or C3-C7cycloalkyl (subgroup AA).

[0065] Within the group AA of compounds of formula I those compounds are preferred wherein X is oxygen (subgroup AB).

[0066] Another group of compounds of formula I within the group AA are those wherein X is sulfur (subgroup AC).

[0067] Within the subgroup AB are those compounds preferred wherein

[0068] R1 is C1-C3alkyl; C1-C3haloalkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C3alkyl, C1-C3haloalkyl or halogen;

[0069] R2 is hydrogen, C1-C4alkyl or C1-C4haloalkyl;

[0070] R3 is C1-C4alkyl, C1-C3haloalkyl or C1-C3alkoxy-C1-C3alkyl;

[0071] A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31, A32 or A33;

[0072] R4 is C5-C7cycloalkyl, unsubstituted or mono- to trisubstituted by halogen; hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cycloalkenyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cyclodialkenyl, unsubstituted or mono- to disubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; thienyl, furyl, isoxazolyl, oxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, which are unsubstituted or substituted by halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy;

[0073] R5 is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; and

[0074] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy (subgroup AB1).

[0075] Within the subgroup AB1 are those compounds more preferred wherein

[0076] A is A1, A2, A3, Al 7, A20, A21, A24, A25, A26, A27, A31 or A33;

[0077] R1 is C1-C2alkyl, C1-C3haloalkyl or cyclopropyl;

[0078] R2 is hydrogen or C1-C3alkyl;

[0079] R3 is C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl;

[0080] R4 is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C1-C2alkyl, C1-C2haloalkyl or C1-C2haloalkoxy; thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4haloalkoxy;

[0081] R5 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy or C1-C3haloalkoxy; and

[0082] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen or C1-C3alkyl (subgroup AB2).

[0083] Preferred compounds whithin the subgroup AB2 are those compounds wherein

[0084] R1 is methyl, ethyl, CFH2 or CF2H;

[0085] R2 is hydrogen;

[0086] R3 is methyl or CH2OCH3;

[0087] A is A31 or A33; and

[0088] R4 is halophenyl, C5-C7cycloalkyl or halothienyl (subgroup AB3).

[0089] Within the subgroup AC are those compounds preferred wherein

[0090] R1 is C1-C3alkyl; C1-C3haloalkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C3alkyl, C1-C3haloalkyl or halogen;

[0091] R2 is hydrogen, C1-C4alkyl or C1-C4haloalkyl;

[0092] R3 is C1-C4alkyl, C1-C3haloalkyl or C1-C3alkoxy-C1-C3alkyl;

[0093] A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31, A32 or A33;

[0094] R4 is C5-C7cycloalkyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cycloalkenyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cyclodialkenyl, unsubstituted or mono- to disubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; thienyl, furyl, isoxazolyl, oxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, which are unsubstituted or substituted by halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy;

[0095] R5 is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; and

[0096] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy (subgroup AC1).

[0097] Within the subgroup AC1 are those compounds more preferred wherein

[0098] A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27, A31 or A33;

[0099] R1 is C1-C2alkyl, C1-C3haloalkyl or cyclopropyl;

[0100] R2 is hydrogen or C1-C3alkyl;

[0101] R3 is C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl;

[0102] R4 is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C1-C2alkyl, C1-C2haloalkyl or C1-C2haloalkoxy; thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4haloalkoxy;

[0103] R5 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy or C1-C3haloalkoxy; and

[0104] R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen or C1-C3alkyl (subgroup AC2).

[0105] The compounds according to formula I may be prepared according to the following reaction schemes.

[0106] A) Synthesis of the Pyrrole Carboxylic Acids:

[0107] Route 1 (Tosmic-route): 10

[0108] Route 2 (“acetoacetic acid”-route, see e.g. EP-326108; J. Am. Chem. Soc. 70,497(1948) or JP-07157466) 11

[0109] B) Synthesis of the Amides/Thioamides, 12

[0110] B1) Synthesis of the Amides Wherein A is Phenyl, Pyridine or Pyrimidine 13

[0111] The “in situ” prepared pyrazole carboxylic acid chloride reacts with an ortho-halosubstituted phenylamine in the presence of a solvent like toluene, benzene, xylene, hexane, cyclohexane, THF, chloroform or methylenechloride and in the presence of a base like sodium carbonate, sodium hydrogencarbonate, potassium carbonate, Hünig base, triethylamine or pyridine at a temperature between 0° C. and reflux temperature. The obtained pyrazolecarboxamide reacts with a boronic acid of the formula R4—B(OH)2 in the presence of a Pd-catalyst like Pd(P(phenyl)3)4, Pd(P(phenyl3))2Cl2, PdCl2dppb, Pd2(dba)3, Pd(OAc)2, PdOAc2/(o-tolyl)3P, Pd(OAc)2/dppf, Pd(PhCN)2Cl2/Ph3As, Pd(CH3CN)2Cl2, Pd2(dba)3/P(tert.butyl)3, Pd(OAc)2/P(tert.butyl)2biphenyl, Pd(OAc)2/TPPTS, Pd(OAc)2/PCy3, Pd(OAc)2/P(O-i-Pr)3, Pd(OAc)2/2-dimethylamino-2′-dicyclohexylphosphinobiphenyl, Pd(OAc)2/2-dimethylamino-2′-ditert.butylphosphinobiphenyl, Pd(OAc)2/(o-biphenyl)P(cyclohexyl)2 in a solvent like 1,2-dimethoxyethane/water, DMF, DMA, THF/water, dioxane/water, benzene, toluene, xylene and others and a base like sodium carbonate, sodium hydrogencarbonate, potassium carbonate, cesium carbonate, potassium phosphate, triethylamine, sodium hydroxide, sodium ethylate, sodium tert.butylate, silver oxide, barium carbonate, potassium fluoride or cesium fluoride at a temperature between 0° C. and reflux temperature.

[0112] B2) Synthesis of Pyrrolecarboxamides Wherein R1 is CF2H 14

[0113] C) Synthesis of the Ortho-Substituted Amines A-NH2:

[0114] The compounds are either known from the literature or can be prepared by known methods. Literature for the synthesis of amine-intermediates and/or amines Ai-NH2:

[0115] A1-NH2: Tetrahedron 1993,49,49-64 or EP-83975 or J. Org. Chem. 1995,60,292;

[0116] A2-NH2: EP-737682;

[0117] A3-NH2: J. Chem. Res. (S) 1978,11,428 or Chem. Scr. 1972,2,245;

[0118] A17-NH2: Org. Prep. Procedures Int. 1989,21,141;

[0119] A21-NH2: J. Chem. Soc. Perkin I 1981,5,1591;

[0120] A25-NH2: Tetrahedron 1993,49,49-64 or Heterocycles 1999,51,721;

[0121] A26-NH2: Synthesis 1996,10,1015 or Synthesis 1994,9,931;

[0122] A27-NH2: Liebigs Ann. Chemie 1977,537-544 or J. Med. Chem. 1975,18,623;

[0123] A31-NH2: EP-315502;

[0124] A32-NH2: J. Pesticide Science 1993,18,245;

[0125] A30-NH2: J. Heterocyclic Chem. 1982,19,1285.

[0126] The invention relates also to the pyrrolecarboxylic acid of formula X, wherein R1, R2 and R3 have the meaning as defined for formula 1.

[0127] Surprisingly, it has now been found that the novel compounds of formula I have, for practical purposes, a very advantageous spectrum of activities for protecting plants against diseases that are caused by fungi as well as by bacteria and viruses.

[0128] The compounds of formula I can be used in the agricultural sector and related fields of use as active ingredients for controlling plant pests. The novel compounds are distinguished by excellent activity at low rates of application, by being well tolerated by plants and by being environmentally safe. They have very useful curative, preventive and systemic properties and are used for protecting numerous cultivated plants. The compounds of formula I can be used to inhibit or destroy the pests that occur on plants or parts of plants (fruit, blossoms, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time protecting also those parts of the plants that grow later e.g. from phytopathogenic microorganisms.

[0129] It is also possible to use compounds of formula I as dressing agents for the treatment of plant propagation material, in particular of seeds (fruit, tubers, grains) and plant cuttings (e.g. rice), for the protection against fungal infections as well as against phytopathogenic fungi occurring in the soil.

[0130] The compounds I are, for example, effective against the phytopathogenic fungi of the following classes: Fungi imperfecti (e.g. Botrytis, Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria) and Basidiomycetes (e.g. Rhizoctonia, Hemileia, Puccinia). Additionally, they are also effective against the Ascomycetes classes (e.g. Venturia and Erysiphe, Podosphaera, Monilinia, Uncinula) and of the Oomycetes classes (e.g. Phytophthora, Pythium, Plasmopara). Outstanding activity has been observed against powdery mildew (Erysiphe spp.). Furthermore, the novel compounds of formula I are effective against phytopathogenic bacteria and viruses (e.g. against Xanthomonas spp, Pseudomonas spp, Erwinia amylovora as well as against the tobacco mosaic virus).

[0131] Within the scope of present invention, target crops to be protected typically comprise the following species of plants: cereal (wheat, barley, rye, oat, rice, maize, sorghum and related species); beet (sugar beet and fodder beet); pomes, drupes and soft fruit (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plants such as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper, vines, hops, bananas and natural rubber plants, as well as ornamentals.

[0132] The compounds of formula I are used in unmodified form or, preferably, together with the adjuvants conventionally employed in the art of formulation. To this end they are conveniently formulated in known manner to emulsifiable concentrates, coatable pastes, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates, and also encapsulations e.g. in polymeric substances. As with the type of the compositions, the methods of application, such as spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances. The compositions may also contain further adjuvants such as stabilizers, antifoams, viscosity regulators, binders or tackifiers as well as fertilizers, micronutrient donors or other formulations for obtaining special effects.

[0133] Suitable carriers and adjuvants can be solid or liquid and are substances useful in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are for example described in WO 97/33890.

[0134] The compounds of formula I are normally used in the form of compositions and can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations which influence the growth of plants. They can also be selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation. The compounds of formula I can be mixed with other fungicides, resulting in some cases in unexpected synergistic activities.

[0135] Mixing components which are particularly preferred are azoles such as azaconazole, bitertanol, propiconazole, difenoconazole, diniconazole, cyproconazole, epoxiconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, tebuconazole, tetraconazole, fenbuconazole, metconazole, myclobutanil, perfurazoate, penconazole, bromuconazole, pyrifenox, prochloraz, triadimefon, triadimenol, triflumizole or triticonazole; pyrimidinyl carbinoles such as ancymidol, fenarimol or nuarimol; 2-amino-pyrimidine such as bupirimate, dimethirimol or ethirimol; morpholines such as dodemorph, fenpropidin, fenpropimorph, spiroxamin or tridemorph; anilinopyrimidines such as cyprodinil, pyrimethanil or mepanipyrim; pyrroles such as fenpiclonil or fludioxonil; phenylamides such as benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace or oxadixyl; benzimidazoles such as benomyl, carbendazim, debacarb, fuberidazole or thiabendazole; dicarboximides such as chlozolinate, dichlozoline, iprodine, myclozoline, procymidone or vinclozolin; carboxamides such as carboxin, fenfuram, flutolanil, mepronil, oxycarboxin or thifluzamide; guanidines such as guazatine, dodine or iminoctadine; strobilurines such as azoxystrobin, kresoxim-methyl, metominostrobin, SSF-129, methyl 2-[(2-trifluoromethyl)-pyrid-6-yloxymethyl]-3-methoxyacrylate or 2-[α{[(α-methyl-3-trifluoromethyl-benzyl)imino]-oxy}-o-tolyl]-glyoxylic acid-methylester-O-methyloxime (trifloxystrobin); dithiocarbamates such as ferbam, mancozeb, maneb, metiram, propineb, thiram, zineb or ziram; N-halomethylthio-dicarboximides such as captafol, captan, dichlofluanid, fluoromide, folpet or tolyfluanid; copper compounds such as Bordeaux mixture, copper hydroxide, copper oxychloride, copper sulfate, cuprous oxide, mancopper or oxine-copper; nitrophenol derivatives such as dinocap or nitrothal-isopropyl; organo phosphorous derivatives such as edifenphos, iprobenphos, isoprothiolane, phosdiphen, pyrazophos or toclofos-methyl; and other compounds of diverse structures such as acibenzolar-S-methyl, anilazine, blasticidin-S, chinomethionat, chloroneb, chlorothalonil, cymoxanil, dichlone, diclomezine, dicloran, diethofencarb, dimethomorph, dithianon, etridiazole, famoxadone, fenamidone, fentin, ferimzone, fluazinam, flusulfamide, fenhexamid, fosetyl-aluminium, hymexazol, kasugamycin, methasulfocarb, pencycuron, phthalide, polyoxins, probenazole, propamocarb, pyroquilon, quinoxyfen, quintozene, sulfur, triazoxide, tricyclazole, triforine, validamycin, (S)-5-methyl-2-methylthio-5-phenyl-3-phenyl-amino-3,5-dihydroimidazol-4-one (RPA 407213), 3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281), N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON 65500), 4-chloro-4-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916), N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)-propionamide (AC 382042), or iprovalicarb (SZX 722).

[0136] A preferred method of applying a compound of formula 1, or an agrochemical composition which contains at least one of said compounds, is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the corresponding pathogen. However, the compounds of formula I can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plant with a liquid formulation, or by applying the compounds in solid form to the soil, e.g. in granular form (soil application). In crops of water rice such granulates can be applied to the flooded rice field. The compounds of formula I may also be applied to seeds (coating) by impregnating the seeds or tubers either with a liquid formulation of the fungicide or coating them with a solid formulation.

[0137] The formulation, i.e. the compositions containing the compound of formula I and, if desired, a solid or liquid adjuvant, are prepared in known manner, typically by intimately mixing and/or grinding the compound with extenders, e.g. solvents, solid carriers and, optionally, surface active compounds (surfactants).

[0138] The agrochemical formulations will usually contain from 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of the compound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant.

[0139] Advantageous rates of application are normally from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seed drenching agent, convenient dosages are from 10 mg to 1 g of active substance per kg of seeds.

[0140] Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.

[0141] The following non-limiting Examples illustrate the above-described invention in more detail. Temperatures are given in degrees Celsius. The following abbreviations are used: m.p.=melting point; b.p.=boiling point. “NMR” means nuclear magnetic resonance spectrum. MS stands for mass spectrum. “%” is percent by weight, unless corresponding concentrations are indicated in other units.

EXAMPLE 1

1,4-Dimethylpyrrole-3-carboxylic Acid

[0142] 15

[0143] In a sulfonation flask 0.87 g (20 mmol) NaH (55%) are dissolved in 10 ml of absolute THF. Then a solution of 2.8 g (20 mmol) 4-methylpyrrole-3-carboxylic acid methylester in 400 ml THF is added dropwise. After stirring of the mixture for 10 minutes at room temperature, 1.2 ml (20 mmol) methyl iodide are added and stirring continued for 1 hour. After addition of 50 ml of a cold ca. 10% ammonium chloride solution the mixture is extracted twice with ethylacetate. After drying of the organic phase the solvent is removed in a water jet vacuum. The obtained crude N-methylated ester is dissolved in 10 ml ethanol and 20 ml of a 2N sodium hydroxide solution. The resulted mixture is stirred at 80-85° C. for 3 hours and then ethanol is removed in a water jet vacuum. After addition of 25 ml of water and extraction with ethylacetate the water phase is acidified with concentrated hydrochloric acid. After cooling the acid is separated by filtration. Yield after drying: 2.1 g of 1,4-dimethylpyrrole-3-carboxylic acid in form of a slightly brownish powder; m.p. 166-168° C.

EXAMPLE 2

1,4-Dimethylpyrrole-3-carboxylic Acid [(4-fluorobiphenyl)-2-yl]amide

[0144] 16

[0145] A solution of 0.49 g (3.5 mmol) 1,4-dimethylpyrrole-3-carboxylic acid and 0.49 g (3.8 mmol) oxalyl chloride in 20 ml of methylene chloride is stirred for 3 hours at room temperature in the presence of a catalytic amount of DMF. Then the acid chloride solution is slowly added to a solution of 0.65 g (3.5 mmol) 2-(4′-fluorophenyl)aniline, 0.43 g (4.2 mmol) triethylamine and 15 ml methylene chloride. The resulting mixture is then stirred for 16 hours at room temperature. After addition of ethylacetate, the organic phase is washed twice with water. Drying of the organic phase (Na2SO4) and removal of the solvent in a water jet vacuum yielded the raw material. Purification by column chromatography over silica gel (eluant:ethylacetate/hexane 1:1) gave 0.55 g 1,4-dimethylpyrrole-3-carboxylic acid [(4-fluorobiphenyl)-2-yl]amide in the form of slightly yellowish powder; m.p.: 147-149° C.

[0146] The following compounds are prepared in a similar way, using analogous methods.

TABLE 1
Compounds of the formula I, wherein A = A1 =
17
Compd.							Phys. data
No.	R1	R2	R3	R4	R5	X	[m.p.]
1.1	CH3	H	CH3	18	H	O
1.2	CH3	H	CH3	19	H	O
1.3	CH3	H	CH3	20	H	O
1.4	CH3	H	CH3	21	H	O
1.5	CH3	H	CH3	22	H	O	resin; MS, 1H-NMR
1.6	CH3	H	CH3	23	H	S
1.7	CH3	H	CH3	24	H	O
1.8	CH3	H	CH3	25	H	O	resin; MS, 1H-NMR
1.9	CH3	H	CH3	26	H	O
1.10	CH3	H	CH3	27	H	O
1.11	CH3	H	CH3	28	H	O
1.12	CH3	CH3	CH3	29	H	O
1.13	CH3	H	CH3	30	H	O
1.14	CH3	H	CH3	31	H	O
1.15	CH3	H	CH3	32	H	O
1.16	CH3	H	CH3	33	H	O
1.17	CH3	H	CH3	34	H	O
1.18	CH3	H	CH3	35	H	O
1.19	CH3	H	CH3	36	H	O
1.20	CH3	H	CH3	37	H	O
1.21	CH3	H	CH3	38	H	O
1.22	CH3	H	CH3	39	H	O
1.23	CH3	H	CH3	40	H	O	156-158
1.24	CH3	H	CH3	41	H	S
1.25	CH3	H	CH3	42	H	O	148-149
1.26	CH3	H	CH3	43	H	S	resin
1.27	CH3	H	CH3	44	H	O
1.28	CH3	H	CH3	45	H	O
1.29	CH3	H	CH3	46	H	O
1.30	CH3	H	CH3	47	H	O
1.31	CH3	H	CH3	48	H	O
1.32	CH3	H	CH3	49	H	O
1.33	CH3	H	CH3	50	H	O
1.34	CH3	H	CH3	51	H	O
1.35	CH3	H	CH3	52	H	O
1.36	CH3	H	CH3	53	H	O
1.37	CH3	H	CH3	54	H	O
1.38	CH3	H	CH3	55	H	O
1.39	CH3	H	CH3	56	H	O
1.40	CH3	H	CH3	57	H	O
1.41	CH3	H	CH3	58	H	O
1.42	CH3	H	CH3	59	H	O
1.43	CH3	H	CH3	60	H	O
1.44	CH3	H	CH3	61	H	O
1.45	CH3	H	CH3	62	H	O
1.46	CH3	H	CH3	63	H	O	118-120
1.47	CH3	H	CH3	64	H	O
1.48	CH3	H	CH3	65	H	O
1.49	CH3	H	CH3	66	H	O
1.50	CH3	H	CH3	67	H	O
1.51	CH3	H	CH3	68	H	O
1.52	CH3	H	CH3	69	H	O
1.53	CH3	H	CH3	70	H	O
1.54	CH3	H	CH3	71	H	O
1.55	CH3	H	CH3	72	H	O
1.56	CH3	H	CH3	73	H	O
1.57	CH3	H	CH3	74	H	O
1.58	CH3	H	CH3	75	H	O
1.59	CH3	H	CH3	76	H	O
1.60	CH3	H	CH3	77	H	O
1.61	CFH2	H	CH3	78	H	O
1.62	CFH2	H	CH3	79	H	O
1.63	CFH2	H	CH3	80	H	O
1.64	CFH2	H	CH3	81	H	O
1.65	CFH2	H	CH3	82	H	O
1.66	CFH2	H	CH3	83	H	S
1.67	CFH2	H	CH3	84	H	O
1.68	CFH2	H	CH3	85	H	O
1.69	CFH2	H	CH3	86	H	O
1.70	CFH2	H	CH3	87	H	O
1.71	CFH2	H	CH3	88	H	O
1.72	CFH2	CH3	CH3	89	H	O
1.73	CFH2	H	CH3	90	H	O
1.74	CFH2	H	CH3	91	H	O
1.75	CFH2	H	CH3	92	H	O
1.76	CFH2	H	CH3	93	H	O
1.77	CFH2	H	CH3	94	H	O
1.78	CFH2	H	CH3	95	H	O
1.79	CFH2	H	CH3	96	H	O
1.80	CFH2	H	CH3	97	H	O
1.81	CFH2	H	CH3	98	H	O
1.82	CFH2	H	CH3	99	H	O
1.83	CFH2	H	CH3	100	H	O
1.84	CFH2	H	CH3	101	H	S
1.85	CFH2	H	CH3	102	H	O
1.86	CFH2	H	CH3	103	H	S
1.87	CFH2	H	CH3	104	H	O
1.88	CFH2	H	CH3	105	H	O
1.89	CFH2	H	CH3	106	H	O
1.90	CFH2	H	CH3	107	H	O
1.91	CFH2	H	CH3	108	H	O
1.92	CFH2	H	CH3	109	H	O
1.93	CFH2	H	CH3	110	H	O
1.94	CFH2	H	CH3	111	H	O
1.95	CFH2	H	CH3	112	H	O
1.96	CFH2	H	CH3	113	H	O
1.97	CFH2	H	CH3	114	H	O
1.98	CFH2	H	CH3	115	H	O
1.99	CFH2	H	CH3	116	H	O
1.100	CFH2	H	CH3	117	H	O
1.101	CFH2	H	CH3	118	H	O
1.102	CFH2	H	CH3	119	H	S
1.103	CFH2	H	CH3	120	H	O
1.104	CFH2	H	CH3	121	H	O
1.105	CFH2	H	CH3	122	H	O
1.106	CFH2	H	CH3	123	H	O
1.107	CFH2	H	CH3	124	H	O
1.108	CFH2	H	CH3	125	H	O
1.109	CFH2	H	CH3	126	H	O
1.110	CFH2	H	CH3	127	H	O
1.111	CFH2	H	CH3	128	H	O
1.112	CFH2	H	CH3	129	H	O
1.113	CFH2	H	CH3	130	H	O
1.114	CFH2	H	CH3	131	H	O
1.115	CFH2	H	CH3	132	H	O
1.116	CFH2	H	CH3	133	H	O
1.117	CFH2	H	CH3	134	H	O
1.118	CFH2	H	CH3	135	H	O
1.119	CFH2	H	CH3	136	H	O
1.120	CFH2	H	CH3	137	H	O
1.121	CFH2	H	CH3	138	H	O
1.122	CF2H	H	CH3	139	H	O
1.123	CF2H	H	CH3	140	H	O
1.124	CF2H	H	CH3	141	H	O
1.125	CF2H	H	CH3	142	H	O
1.126	CF2H	H	CH3	143	H	O
1.127	CF2H	H	CH3	144	H	S
1.128	CF2H	H	CH3	145	H	O
1.129	CF2H	H	CH3	146	H	O
1.130	CF2H	H	CH3	147	H	O
1.131	CF2H	H	CH3	148	H	O
1.132	CF2H	H	CH3	149	H	O
1.133	CF2H	CH3	CH3	150	H	O
1.134	CF2H	H	CH3	151	H	O
1.135	CF2H	H	CH3	152	H	O
1.136	CF2H	H	CH3	153	H	O
1.137	CF2H	H	CH3	154	H	O
1.138	CF2H	H	CH3	155	H	O
1.139	CF2H	H	CH3	156	H	O
1.140	CF2H	H	CH3	157	H	O
1.141	CF2H	H	CH3	158	H	O
1.142	CF2H	H	CH3	159	H	O
1.143	CF2H	H	CH3	160	H	O
1.144	CF2H	H	CH3	161	H	O	resin
1.145	CF2H	H	CH3	162	H	S
1.146	CF2H	H	CH3	163	H	O
1.147	CF2H	H	CH3	164	H	S
1.148	CF2H	H	CH3	165	H	O
1.149	CF2H	H	CH3	166	H	O
1.150	CF2H	H	CH3	167	H	O
1.151	CF2H	H	CH3	168	H	O
1.152	CF2H	H	CH3	169	H	O
1.153	CF2H	H	CH3	170	H	O	resin, MS
1.154	CF2H	H	CH3	171	H	O
1.155	CF2H	H	CH3	172	H	O
1.156	CF2H	H	CH3	173	H	O
1.157	CF2H	H	CH3	174	H	O
1.158	CF2H	H	CH3	175	H	O
1.159	CF2H2	H	CH3	176	H	O
1.160	CF2H	H	CH3	177	H	O
1.161	CF2H	H	CH3	178	H	O
1.162	CF2H	H	CH3	179	H	O
1.163	CF2H	H	CH3	180	H	S
1.164	CF2H	H	CH3	181	H	O
1.165	CF2H	H	CH3	182	H	O
1.166	CF2H	H	CH3	183	H	O
1.167	CF2H	H	CH3	184	H	O
1.168	CF2H	H	CH3	185	H	O
1.169	CF2H	H	CH3	186	H	O
1.170	CF2H	H	CH3	187	H	O
1.171	CF2H	H	CH3	188	H	O
1.172	CF2H	H	CH3	189	H	O
1.173	CF2H	H	CH3	190	H	O
1.174	CF2H	H	CH3	191	H	O
1.175	CF2H	H	CH3	192	H	O
1.176	CF2H	H	CH3	193	H	O
1.177	CF2H	H	CH3	194	H	O
1.178	CF2H	H	CH3	195	H	O
1.179	CF2H	H	CH3	196	H	O
1.180	CF2H	H	CH3	197	H	O
1.181	CF2H	H	CH3	198	H	O
1.182	CF2H	H	CH3	199	H	O
1.183	CF2CF3	H	CH3	200	H	O	113-114
1.184	CF2CF3	H	CH3	201	H	S
1.185	CF2CF3	H	CH3	202	H	O
1.186	CF2CF3	H	CH3	203	H	O
1.187	CF2CF3	H	CH3	204	H	O	120-121
1.188	CF2CF3	H	CH3	205	H	O
1.189	CF2CF3	H	CH3	206	H	O
1.190	CF2CF3	H	CH3	207	H	O	148-150
1.191	CF2CF3	H	CH3	208	H	S
1.192	CF2CF3	H	CH3	209	H	O	134-136
1.193	CF2CF3	H	CH3	210	H	S
1.194	CF2CF3	H	CH3	211	H	O
1.195	CF2CF3	H	CH3	212	H	O
1.196	CF2CF3	H	CH3	213	H	O
1.197	CF2CF3	H	CH3	214	H	O
1.198	Δ	H	CH3	215	H	O
1.199	Δ	H	CH3	216	H	O
1.200	Δ	H	CH3	217	H	O
1.201	Δ	H	CH3	218	H	O
1.202	Δ	H	CH3	219	H	O
1.203	Δ	H	CH3	220	H	S
1.204	Δ	H	CH3	221	H	O
1.205	Δ	H	CH3	222	H	O
1.206	Δ	H	CH3	223	H	O	resin;MS, 1H-NMR
1.207	Δ	H	CH3	224	H	O
1.208	Δ	H	CH3	225	H	O
1.209	Δ	CH3	CH3	226	H	O
1.210	Δ	H	CH3	227	H	O
1.211	Δ	H	CH3	228	H	O
1.212	Δ	H	CH3	229	H	O
1.213	Δ	H	CH3	230	H	O
1.214	Δ	H	CH3	231	H	O
1.215	Δ	H	CH3	232	H	O
1.216	Δ	H	CH3	233	H	O
1.217	Δ	H	CH3	234	H	O
1.218	Δ	H	CH3	235	H	O
1.219	Δ	H	CH3	236	H	O
1.220	Δ	H	CH3	237	H	O
1.221	Δ	H	CH3	238	H	S
1.222	Δ	H	CH3	239	H	O
1.223	Δ	H	CH3	240	H	S
1.224	Δ	H	CH3	241	H	O
1.225	Δ	H	CH3	242	H	O
1.226	Δ	H	CH3	243	H	O
1.227	Δ	H	CH3	244	H	O
1.228	Δ	H	CH3	245	H	O
1.229	Δ	H	CH3	246	H	O
1.230	Δ	H	CH3	247	H	O
1.231	Δ	H	CH3	248	H	O
1.232	Δ	H	CH3	249	H	O
1.233	Δ	H	CH3	250	H	O
1.234	Δ	H	CH3	251	H	O
1.235	Δ	H	CH3	252	H	O
1.236	Δ	H	CH3	253	H	O
1.237	Δ	H	CH3	254	H	O
1.238	Δ	H	CH3	255	H	O
1.239	Δ	H	CH3	256	H	S
1.240	Δ	H	CH3	257	H	O
1.241	Δ	H	CH3	258	H	O
1.242	Δ	H	CH3	259	H	O
1.243	Δ	H	CH3	260	H	O
1.244	Δ	H	CH3	261	H	O	105-107
1.245	Δ	H	CH3	262	H	O
1.246	Δ	H	CH3	263	H	O
1.247	Δ	H	CH3	264	H	O
1.248	Δ	H	CH3	265	H	O
1.249	Δ	H	CH3	266	H	O
1.250	Δ	H	CH3	267	H	O
1.251	Δ	H	CH3	268	H	O
1.252	Δ	H	CH3	269	H	O
1.253	Δ	H	CH3	270	H	O
1.254	Δ	H	CH3	271	H	O
1.255	Δ	H	CH3	272	H	O
1.256	Δ	H	CH3	273	H	O
1.257	Δ	H	CH3	274	H	O
1.258	Δ	H	CH3	275	H	O
1.259	CH3	H	CH3	276	H	S
1.260	CH2CH3	H	CH3	277	H	O	152-153
1.261	CH2CH3	H	CH3	278	H	O	120-121
1.262	CH2CH3	H	CH3	279	H	O
1.263	CH2CH3	H	CH3	280	H	O
1.264	CH2CH3	H	CH3	281	H	O
1.265	CH2CH3	H	CH2CH3	282	H	O	97-98
1.266	CH2CH3	H	CH2CH3	283	H	O	95-96
1.267	CH2CH3	H	CH2CH3	284	H	O
1.268	(CH3)2CH	H	CH3	285	H	O	102-103
1.269	(CH3)2CH	H	CH3	286	H	O	99-100
1.270	(CH3)2CH	H	CH3	287	H	O
1.271	(CH3)2CH	H	CH2CH3	288	H	O	116-117
1.272	(CH3)2CH	H	CH2CH3	289	H	O	93-94

[0147]

TABLE 2
Compounds of the formula I, where A = A2 =
290
Compd.							Phys. data
No.	R1	R2	R3	R4	R5	X	[m.p.]
2.1	CH3	H	CH3	291	H	O
2.2	CH3	H	CH3	292	H	O
2.3	CH3	H	CH3	293	H	O
2.4	CH3	H	CH3	294	H	O
2.5	CH3	H	CH3	295	H	O
2.6	CH3	H	CH3	296	H	S
2.7	CH3	H	CH3	297	H	O
2.8	CH3	H	CH3	298	H	O
2.9	CH3	H	CH3	299	H	O
2.10	CH3	H	CH3	300	H	O
2.11	CH3	H	CH3	301	H	O
2.12	CH3	CH3	CH3	302	H	O
2.13	CH3	H	CH3	303	H	O
2.14	CH3	H	CH3	304	H	O
2.15	CH3	H	CH3	305	H	O
2.16	CH3	H	CH3	306	H	O
2.17	CH3	H	CH3	307	H	O
2.18	CH3	H	CH3	308	H	O
2.19	CH3	H	CH3	309	H	O
2.20	CH3	H	CH3	310	H	O
2.21	CH3	H	CH3	311	H	O
2.22	CH3	H	CH3	312	H	O
2.23	CH3	H	CH3	313	H	O	resin,MS
2.24	CH3	H	CH3	314	H	S
2.25	CH3	H	CH3	315	H	O
2.26	CH3	H	CH3	316	H	S
2.27	CH3	H	CH3	317	H	O
2.28	CH3	H	CH3	318	H	O
2.29	CH3	H	CH3	319	H	O
2.30	CH3	H	CH3	320	H	O
2.31	CH3	H	CH3	321	H	O
2.32	CH3	H	CH3	322	H	O
2.33	CH3	H	CH3	323	H	O
2.34	CH3	H	CH3	324	H	O
2.35	CH3	H	CH3	325	H	O
2.36	CH3	H	CH3	326	H	O
2.37	CH3	H	CH3	327	H	O
2.28	CH3	H	CH3	328	H	O
2.39	CH3	H	CH3	329	H	O
2.40	CH3	H	CH3	330	H	O
2.41	CH3	H	CH3	331	H	O
2.42	CH3	H	CH3	332	H	S
2.43	CH3	H	CH3	333	H	O
2.44	CH3	H	CH3	334	H	O
2.45	CH3	H	CH3	335	H	O
2.46	CH3	H	CH3	336	H	O
2.47	CH3	H	CH3	337	H	O
2.48	CH3	H	CH3	338	H	O
2.49	CH3	H	CH3	339	H	O
2.50	CH3	H	CH3	340	H	O
2.51	CH3	H	CH3	341	H	O
2.52	CH3	H	CH3	342	H	O
2.53	CH3	H	CH3	343	H	O
2.54	CH3	H	CH3	344	H	O
2.55	CH3	H	CH3	345	H	O
2.56	CH3	H	CH3	346	H	O
2.57	CH3	H	CH3	347	H	O
2.58	CH3	H	CH3	348	H	O
2.59	CH3	H	CH3	349	H	O
2.60	CH3	H	CH3	350	H	O
2.61	CFH2	H	CH3	351	H	O
2.62	CFH2	H	CH3	352	H	O
2.63	CFH2	H	CH3	353	H	O
2.64	CFH2	H	CH3	354	H	O
2.65	CFH2	H	CH3	355	H	O
2.66	CFH2	H	CH3	356	H	S
2.67	CFH2	H	CH3	357	H	O
2.68	CFH2	H	CH3	358	H	O
2.69	CFH2	H	CH3	359	H	O
2.70	CFH2	H	CH3	360	H	O
2.71	CFH2	H	CH3	361	H	O
2.72	CFH2	CH3	CH3	362	H	O
2.73	CFH2	H	CH3	363	H	O
2.74	CFH2	H	CH3	364	H	O
2.75	CFH2	H	CH3	365	H	O
2.76	CFH2	H	CH3	366	H	O
2.77	CFH2	H	CH3	367	H	O
2.78	CFH2	H	CH3	368	H	O
2.79	CFH2	H	CH3	369	H	O
2.80	CFH2	H	CH3	370	H	O
2.81	CFH2	H	CH3	371	H	O
2.82	CFH2	H	CH3	372	H	O
2.83	CFH2	H	CH3	373	H	O
2.84	CFH2	H	CH3	374	H	S
2.85	CFH2	H	CH3	375	H	O
2.86	CFH2	H	CH3	376	H	S
2.87	CFH2	H	CH3	377	H	O
2.88	CFH2	H	CH3	378	H	O
2.90	CFH2	H	CH3	379	H	O
2.91	CFH2	H	CH3	380	H	O
2.92	CFH2	H	CH3	381	H	O
2.93	CFH2	H	CH3	382	H	O
2.94	CFH2	H	CH3	383	H	O
2.95	CFH2	H	CH3	384	H	O
2.96	CFH2	H	CH3	385	H	O
2.97	CFH2	H	CH3	386	H	O
2.98	CFH2	H	CH3	387	H	O
2.99	CFH2	H	CH3	388	H	O
2.100	CFH2	H	CH3	389	H	O
2.101	CFH2	H	CH3	390	H	O
2.102	CFH2	H	CH3	391	H	S
2.103	CFH2	H	CH3	392	H	O
2.104	CFH2	H	CH3	393	H	O
2.105	CFH2	H	CH3	394	H	O
2.106	CFH2	H	CH3	395	H	O
2.107	CFH2	H	CH3	396	H	O
2.108	CFH2	H	CH3	397	H	O
2.109	CFH2	H	CH3	398	H	O
2.110	CFH2	H	CH3	399	H	O
2.111	CFH2	H	CH3	400	H	O
2.112	CFH2	H	CH3	401	H	O
2.113	CFH2	H	CH3	402	H	O
2.114	CFH2	H	CH3	403	H	O
2.115	CFH2	H	CH3	404	H	O
2.116	CFH2	H	CH3	405	H	O
2.117	CFH2	H	CH3	406	H	O
2.118	CFH2	H	CH3	407	H	O
2.119	CFH2	H	CH3	408	H	O
2.120	CFH2	H	CH3	409	H	O
2.121	CFH2	H	CH3	410	H	O
2.122	CF2H	H	CH3	411	H	O
2.123	CF2H	H	CH3	412	H	O
2.124	CF2H	H	CH3	413	H	O
2.125	CF2H	H	CH3	414	H	O
2.126	CF2H	H	CH3	415	H	O
2.127	CF2H	H	CH3	416	H	S
2.128	CF2H	H	CH3	417	H	O
2.129	CF2H	H	CH3	418	H	O
2.130	CF2H	H	CH3	419	H	O
2.131	CF2H	H	CH3	420	H	O
2.132	CF2H	H	CH3	421	H	O
2.133	CF2H	CH3	CH3	422	H	O
2.134	CF2H	H	CH3	423	H	O
2.135	CF2H	H	CH3	424	H	O
2.136	CF2H	H	CH3	425	H	O
2.137	CF2H	H	CH3	426	H	O
2.138	CF2H	H	CH3	427	H	O
2.139	CF2H	H	CH3	428	H	O
2.140	CF2H	H	CH3	429	H	O
2.141	CF2H	H	CH3	430	H	O
2.142	CF2H	H	CH3	431	H	O
2.143	CF2H	H	CH3	432	H	O
2.144	CF2H	H	CH3	433	H	O
2.145	CF2H	H	CH3	434	H	O
2.146	CF2H	H	CH3	435	H	S
2.147	CF2H	H	CH3	436	H	O
2.148	CF2H	H	CH3	437	H	S
2.149	CF2H	H	CH3	438	H	O
2.150	CF2H	H	CH3	439	H	O
2.151	CF2H	H	CH3	440	H	O
2.152	CF2H2	H	CH3	441	H	O
2.153	CF2H	H	CH3	442	H	O
2.154	CF2H	H	CH3	443	H	O
2.155	CF2H	H	CH3	444	H	O
2.156	CF2H	H	CH3	445	H	O
2.157	CF2H	H	CH3	446	H	O
2.158	CF2H	H	CH3	447	H	O
2.159	CF2H2	H	CH3	448	H	O
2.160	CF2H	H	CH3	449	H	O
2.161	CF2H	H	CH3	450	H	O
2.162	CF2H	H	CH3	451	H	O
2.163	CF2H	H	CH3	452	H	S
2.164	CF2H	H	CH3	453	H	O
2.165	CF2H	H	CH3	454	H	O
2.166	CF2H	H	CH3	455	H	O
2.167	CF2H	H	CH3	456	H	O
2.168	CF2H	H	CH3	457	H	O
2.169	CF2H	H	CH3	458	H	O
2.170	CF2H	H	CH3	459	H	O
2.171	CF2H	H	CH3	460	H	O
2.172	CF2H	H	CH3	461	H	O
2.173	CF2H	H	CH3	462	H	O
2.174	CF2H	H	CH3	463	H	O
2.175	CF2H	H	CH3	464	H	O
2.176	CF2H	H	CH3	465	H	O
2.177	CF2H	H	CH3	466	H	O
2.178	CF2H	H	CH3	467	H	O
2.179	CF2H	H	CH3	468	H	O
2.180	CF2H	H	CH3	469	H	O
2.181	CF2H	H	CH3	470	H	O
2.182	CF2H	H	CH3	471	H	O
2.183	CF2CF3	H	CH3	472	H	O
2.184	CF2CF3	H	CH3	473	H	S
2.185	CF2CF3	H	CH3	474	H	O
2.186	CF2CF3	H	CH3	475	H	O
2.187	CF2CF3	H	CH3	476	H	O
2.188	CF2CF3	H	CH3	477	H	O
2.189	CF2CF3	H	CH3	478	H	O
2.190	CF2CF3	H	CH3	479	H	O	145-146
2.191	CF2CF3	H	CH3	480	H	S
2.192	CF2CF3	H	CH3	481	H	O	136-137
2.193	CF2CF3	H	CH3	482	H	S
2.194	CF2CF3	H	CH3	483	H	O
2.195	CF2CF3	H	CH3	484	H	O
2.196	CF2CF3	H	CH3	485	H	O
2.197	CF2CF3	H	CH3	486	H	O
2.198	Δ	H	CH3	487	H	O
2.199	Δ	H	CH3	488	H	O
2.200	Δ	H	CH3	489	H	O
2.201	Δ	H	CH3	490	H	O
2.202	Δ	H	CH3	491	H	O
2.203	Δ	H	CH3	492	H	S
2.204	Δ	H	CH3	493	H	O
2.205	Δ	H	CH3	494	H	O
2.206	Δ	H	CH3	495	H	O
2.207	Δ	H	CH3	496	H	O
2.208	Δ	H	CH3	497	H	O
2.209	Δ	CH3	CH3	498	H	O
2.210	Δ	H	CH3	499	H	O
2.211	Δ	H	CH3	500	H	O
2.212	Δ	H	CH3	501	H	O
2.213	Δ	H	CH3	502	H	O
2.214	Δ	H	CH3	503	H	O
2.215	Δ	H	CH3	504	H	O
2.216	Δ	H	CH3	505	H	O
2.217	Δ	H	CH3	506	H	O
2.218	Δ	H	CH3	507	H	O
2.219	Δ	H	CH3	508	H	O
2.220	Δ	H	CH3	509	H	O
2.221	Δ	H	CH3	510	H	O
2.222	Δ	H	CH3	511	H	O
2.223	Δ	H	CH3	512	H	S
2.224	Δ	H	CH3	513	H	O
2.225	Δ	H	CH3	514	H	O
2.226	Δ	H	CH3	515	H	O
2.227	Δ	H	CH3	516	H	O
2.228	Δ	H	CH3	517	H	O
2.229	Δ	H	CH3	518	H	O
2.230	Δ	H	CH3	519	H	O
2.231	Δ	H	CH3	520	H	O
2.232	Δ	H	CH3	521	H	O
2.233	Δ	H	CH3	522	H	O
2.234	Δ	H	CH3	523	H	O
2.235	Δ	H	CH3	524	H	O
2.237	Δ	H	CH3	525	H	O
2.238	Δ	H	CH3	526	H	O
2.239	Δ	H	CH3	527	H	S
2.240	Δ	H	CH3	528	H	O
2.241	Δ	H	CH3	529	H	O
2.242	Δ	H	CH3	530	H	O
2.243	Δ	H	CH3	531	H	O
2.244	Δ	H	CH3	532	H	O
2.245	Δ	H	CH3	533	H	O
2.247	Δ	H	CH3	534	H	O
2.248	Δ	H	CH3	535	H	O
2.249	Δ	H	CH3	536	H	O
2.250	Δ	H	CH3	537	H	O
2.251	Δ	H	CH3	538	H	O
2.252	Δ	H	CH3	539	H	O
2.253	Δ	H	CH3	540	H	O
2.254	Δ	H	CH3	541	H	O
2.255	Δ	H	CH3	542	H	O
2.256	Δ	H	CH3	543	H	O
2.257	Δ	H	CH3	544	H	O
2.258	Δ	H	CH3	545	H	O
2.259	CH3	H	CH3	546	H	O
2.260	CH2CH3	H	CH3	547	H	O
2.261	CH2CH3	H	CH3	548	H	O

[0148]

TABLE 3
Compound of the formula I, wherein A = A17 =
549
Compd.							Phys.data
No.	R1	R2	R3	R4	R5	X	[m.p.]
3.1	CH3	H	CH3	550	H	O
3.2	CH3	H	CH3	551	H	S
3.3	CH3	H	CH3	552	H	O
3.4	CH3	H	CH3	553	H	O
3.5	CH3	H	CH3	554	H	O
3.6	CH3	H	CH3	555	H	O
3.7	CH3	H	CH3	556	H	O
3.8	CH3	H	CH3	557	H	O
3.9	CH3	H	CH3	558	H	O
3.10	CH3	H	CH3	559	H	O
3.11	CH3	H	CH3	560	H	S
3.12	CH3	H	CH3	561	H	O
3.13	CH3	H	CH3	562	H	S
3.14	CH3	H	CH3	563	H	O
3.15	CH3	H	CH3	564	H	O
3.16	CH3	H	CH3	565	H	O
3.17	CH3	H	CH3	566	H	O
3.18	CH3	H	CH3	567	H	O
3.19	CH3	H	CH3	568	H	O
3.20	CH3	H	CH3	569	H	O
3.21	CH3	H	CH3	570	H	O
3.22	CH3	H	CH3	571	H	O
3.23	CH3	H	CH3	572	H	O
3.24	CH3	H	CH3	573	H	O
3.25	CH3	H	CH3	574	H	O
3.26	CH3	H	CH3	575	H	S
3.27	CH3	H	CH3	576	H	O
3.28	CH3	H	CH3	577	H	O
3.29	CH3	H	CH3	578	H	O
3.30	CH3	H	CH3	579	H	O
3.31	CH3	H	CH3	580	H	O
3.32	CH3	H	CH3	581	H	O
3.33	CH3	H	CH3	582	H	O
3.34	CH3	H	CH3	583	H	O
3.35	CH3	H	CH3	584	H	O
3.36	CH3	H	CH3	585	H	O
3.37	CH3	H	CH3	586	H	O
3.38	CH3	H	CH3	587	H	O
3.39	CH3	H	CH3	588	H	O
3.40	CH3	H	CH3	589	H	O
3.41	Δ	H	CH3	590	H	O
3.42	Δ	H	CH3	591	H	S
3.43	Δ	H	CH3	592	H	O
3.44	Δ	H	CH3	593	H	O
3.45	Δ	H	CH3	594	H	O
3.46	Δ	H	CH3	595	H	O
3.47	Δ	H	CH3	596	H	O
3.48	Δ	H	CH3	597	H	O
3.49	Δ	H	CH3	598	H	O
3.50	Δ	H	CH3	599	H	S
3.51	Δ	H	CH3	600	H	O
3.52	Δ	H	CH3	601	H	S
3.53	Δ	H	CH3	602	H	O
3.54	Δ	H	CH3	603	H	O
3.55	Δ	H	CH3	604	H	O
3.56	Δ	H	CH3	605	H	O
3.57	Δ	H	CH3	606	H	O
3.58	Δ	H	CH3	607	H	S
3.61	Δ	H	CH3	608	H	O
3.60	Δ	H	CH3	609	H	O
3.61	Δ	H	CH3	610	H	O
3.62	Δ	H	CH3	611	H	O
3.63	Δ	H	CH3	612	H	O
3.64	Δ	H	CH3	613	H	O
3.65	Δ	H	CH3	614	H	O
3.66	Δ	H	CH3	615	H	O
3.67	Δ	H	CH3	616	H	O
3.68	Δ	H	CH3	617	H	O
3.69	Δ	H	CH3	618	H	O
3.70	CF2H	H	CH3	619	H	O
3.71	CF2H	H	CH3	620	H	S
3.72	CF2H	H	CH3	621	H	O
3.73	CF2H	H	CH3	622	H	O
3.74	CF2H	H	CH3	623	H	O
3.75	CF2H	H	CH3	624	H	O
3.76	CF2H	H	CH3	625	H	O
3.77	CF2H	H	CH3	626	H	O
3.78	CF2H	H	CH3	627	H	O
3.79	CF2H	H	CH3	628	H	S
3.80	CF2H	H	CH3	629	H	O
3.81	CF2H	H	CH3	630	H	S
3.82	CF2H	H	CH3	631	H	O
3.83	CF2H	H	CH3	632	H	O
3.84	CF2H	H	CH3	633	H	O
3.85	CF2H	H	CH3	634	H	O
3.86	CF2H	H	CH3	635	H	O
3.87	CF2H	H	CH3	636	H	S
3.88	CF2H	H	CH3	637	H	O
3.89	CF2H	H	CH3	638	H	O
3.90	CF2H	H	CH3	639	H	O
3.91	CF2H	H	CH3	640	H	O
3.92	CF2H	H	CH3	641	H	O
3.93	CF2H	H	CH3	642	H	O
3.94	CF2H	H	CH3	643	H	O
3.95	CF2H	H	CH3	644	H	O
3.96	CF2H	H	CH3	645	H	O
3.97	CF2H	H	CH3	646	H	O
3.98	CF2H	H	CH3	647	H	O

[0149]

TABLE 4
Compounds of the formula I, wherein A = A21 =
648
Compd.						Phys.data
No.	R1	R2	R3	R4	X	[m.p.]
4.1	CH3	H	CH3	649	O
4.2	CH3	H	CH3	650	S
4.3	CH3	H	CH3	651	O
4.4	CH3	H	CH3	652	O
4.5	CH3	H	CH3	653	O
4.6	CH3	H	CH3	654	O
4.7	CH3	H	CH3	655	O
4.8	CH3	H	CH3	656	O
4.9	CH3	H	CH3	657	O
4.10	CH3	H	CH3	658	O
4.11	CH3	H	CH3	659	S
4.12	CH3	H	CH3	660	O
4.13	CH3	H	CH3	661	H	S
4.14	CH3	H	CH3	662	O
4.15	CH3	H	CH3	663	O
4.16	CH3	H	CH3	664	O
4.17	CH3	H	CH3	665	O
4.18	CH3	H	CH3	666	O
4.19	CH3	H	CH3	667	O
4.20	CH3	H	CH3	668	O
4.21	CH3	H	CH3	669	O
4.22	CH3	H	CH3	670	O
4.23	CH3	H	CH3	671	O
4.24	CH3	H	CH3	672	O
4.25	CH3	H	CH3	673	O
4.26	CH3	H	CH3	674	H	S
4.27	CH3	H	CH3	675	H	O
4.28	CH3	H	CH3	676	O
4.29	CH3	H	CH3	677	O
4.30	CH3	H	CH3	678	O
4.31	CH3	H	CH3	679	O
4.32	CH3	H	CH3	680	O
4.33	CH3	H	CH3	681	O
4.34	CH3	H	CH3	682	O
4.35	CH3	H	CH3	683	O
4.36	CH3	H	CH3	684	O
4.37	CH3	H	CH3	685	O
4.38	CH3	H	CH3	686	O
4.39	CH3	H	CH3	687	O
4.40	CH3	H	CH3	688	O
4.41	Δ	H	CH3	689	O
4.42	Δ	H	CH3	690	H	S
4.43	Δ	H	CH3	691	O
4.44	Δ	H	CH3	692	O
4.45	Δ	H	CH3	693	H	O
4.46	Δ	H	CH3	694	O
4.47	Δ	H	CH3	695	O
4.48	Δ	H	CH3	696	O
4.49	Δ	H	CH3	697	O
4.50	Δ	H	CH3	698	S
4.51	Δ	H	CH3	699	O
4.52	Δ	H	CH3	700	S
4.53	Δ	H	CH3	701	O
4.54	Δ	H	CH3	702	O
4.55	Δ	H	CH3	703	O
4.56	Δ	H	CH3	704	O
4.57	Δ	H	CH3	705	H	O
4.58	Δ	H	CH3	706	H	S
4.61	Δ	H	CH3	707	H	O
4.60	Δ	H	CH3	708	O
4.61	Δ	H	CH3	709	O
4.62	Δ	H	CH3	710	O
4.63	Δ	H	CH3	711	O
4.64	Δ	H	CH3	712	O
4.65	Δ	H	CH3	713	O
4.66	Δ	H	CH3	714	O
4.67	Δ	H	CH3	715	O
4.68	Δ	H	CH3	716	O
4.69	Δ	H	CH3	717	O
4.70	CF2H	H	CH3	718	O
4.71	CF2H	H	CH3	719	H	S
4.72	CF2H	H	CH3	720	O
4.73	CF2H	H	CH3	721	O
4.74	CF2H	H	CH3	722	O
4.75	CF2H	H	CH3	723	O
4.76	CF2H	H	CH3	724	O
4.77	CF2H	H	CH3	725	O
4.78	CF2H	H	CH3	726	O
4.79	CF2H	H	CH3	727	H	S
4.80	CF2H	H	CH3	728	O
4.81	CF2H	H	CH3	729	H	S
4.82	CF2H	H	CH3	730	O
4.83	CF2H	H	CH3	731	O
4.84	CF2H	H	CH3	732	O
4.85	CF2H	H	CH3	733	O
4.86	CF2H	H	CH3	734	H	O
4.87	CF2H	H	CH3	735	S
4.88	CF2H	H	CH3	736	H	O
4.89	CF2H	H	CH3	737	O
4.90	CF2H	H	CH3	738	O
4.91	CF2H	H	CH3	739	O
4.92	CF2H	H	CH3	740	O
4.93	CF2H	H	CH3	741	O
4.94	CF2H	H	CH3	742	O
4.95	CF2H	H	CH3	743	O
4.96	CF2H	H	CH3	744	O
4.97	CF2H	H	CH3	745	O
4.98	CF2H	H	CH3	746	O

[0150]

TABLE 5
Compounds of the formula I, wherein A = A24 =
747
Compd.							Phys.data
No.	R1	R2	R3	R4	R5	X	[m.p.]
5.1	CH3	H	CH3	748	H	O
5.2	CH3	H	CH3	749	H	S
5.3	CH3	H	CH3	750	H	O
5.4	CH3	H	CH3	751	H	O
5.5	CH3	H	CH3	752	H	O
5.6	CH3	H	CH3	753	H	O
5.7	CH3	H	CH3	754	H	O
5.8	CH3	H	CH3	755	H	O
5.9	CH3	H	CH3	756	H	O
5.10	CH3	H	CH3	757	H	O
5.11	CH3	H	CH3	758	H	S
5.12	CH3	H	CH3	759	H	O
5.13	CH3	H	CH3	760	H	S
5.14	CH3	H	CH3	761	H	O
5.15	CH3	H	CH3	762	H	O
5.16	CH3	H	CH3	763	H	O
5.17	CH3	H	CH3	764	H	O
5.18	CH3	H	CH3	765	H	O
5.19	CH3	H	CH3	766	H	O
5.20	CH3	H	CH3	767	H	O
5.21	CH3	H	CH3	768	H	O
5.22	CH3	H	CH3	769	H	O
5.23	CH3	H	CH3	770	H	O
5.24	CH3	H	CH3	771	H	O
5.25	CH3	H	CH3	772	H	O
5.26	CH3	H	CH3	773	H	S
5.27	CH3	H	CH3	774	H	O
5.28	CH3	H	CH3	775	H	O
5.29	CH3	H	CH3	776	H	O
5.30	CH3	H	CH3	777	H	O
5.31	CH3	H	CH3	778	H	O
5.32	CH3	H	CH3	779	H	O
5.33	CH3	H	CH3	780	H	O
5.34	CH3	H	CH3	781	H	O
5.35	CH3	H	CH3	782	H	O
5.36	CH3	H	CH3	783	H	O
5.37	CH3	H	CH3	784	H	O
5.38	CH3	H	CH3	785	H	O
5.39	CH3	H	CH3	786	H	O
5.40	CH3	H	CH3	787	H	O
5.41	Δ	H	CH3	788	H	O
5.42	Δ	H	CH3	789	H	S
5.43	Δ	H	CH3	790	H	O
5.44	Δ	H	CH3	791	H	O
5.45	Δ	H	CH3	792	H	O
5.46	Δ	H	CH3	793	H	O
5.47	Δ	H	CH3	794	H	O
5.48	Δ	H	CH3	795	H	O
5.49	Δ	H	CH3	796	H	O
5.50	Δ	H	CH3	797	H	S
5.51	Δ	H	CH3	798	H	O
5.52	Δ	H	CH3	799	H	S
5.53	Δ	H	CH3	800	H	O
5.54	Δ	H	CH3	801	H	O
5.55	Δ	H	CH3	802	H	O
5.56	Δ	H	CH3	803	H	O
5.57	Δ	H	CH3	804	H	O
5.58	Δ	H	CH3	805	H	S
5.61	Δ	H	CH3	806	H	O
5.60	Δ	H	CH3	807	H	O
5.61	Δ	H	CH3	808	H	O
5.62	Δ	H	CH3	809	H	O
5.63	Δ	H	CH3	810	H	O
5.64	Δ	H	CH3	811	H	O
5.65	Δ	H	CH3	812	H	O
5.66	Δ	H	CH3	813	H	O
5.67	Δ	H	CH3	814	H	O
5.68	Δ	H	CH3	815	H	O
5.69	Δ	H	CH3	816	H	O
5.70	CF2H	H	CH3	817	H	O
5.71	CF2H	H	CH3	818	H	S
5.72	CF2H	H	CH3	819	H	O
5.73	CF2H	H	CH3	820	H	O
5.74	CF2H	H	CH3	821	H	O
5.75	CF2H	H	CH3	822	H	O
5.76	CF2H	H	CH3	823	H	O
5.77	CF2H	H	CH3	824	H	O
5.78	CF2H	H	CH3	825	H	O
5.79	CF2H	H	CH3	826	H	S
5.80	CF2H	H	CH3	827	H	O
5.81	CF2H	H	CH3	828	H	S
5.82	CF2H	H	CH3	829	H	O
5.83	CF2H	H	CH3	830	H	O
5.84	CF2H	H	CH3	831	H	O
5.85	CF2H	H	CH3	832	H	O
5.86	CF2H	H	CH3	833	H	O
5.87	CF2H	H	CH3	834	H	S
5.88	CF2H	H	CH3	835	H	O
5.89	CF2H	H	CH3	836	H	O
5.90	CF2H	H	CH3	837	H	O
5.91	CF2H	H	CH3	838	H	O
5.92	CF2H	H	CH3	839	H	O
5.93	CF2H	H	CH3	840	H	O
5.94	CF2H	H	CH3	841	H	O
5.95	CF2H	H	CH3	842	H	O
5.96	CF2H	H	CH3	843	H	O
5.97	CF2H	H	CH3	844	H	O
5.98	CF2H	H	CH3	845	H	O

[0151]

TABLE 6
Compounds of the formula I, wherein A = A25 =
846
Compd.							Phys.data
No.	R1	R2	R3	R4	R5	X	[m.p.]
6.1	CH3	H	CH3	847	H	O
6.2	CH3	H	CH3	848	H	S
6.3	CH3	H	CH3	849	H	O
6.4	CH3	H	CH3	850	H	O
6.5	CH3	H	CH3	851	H	O
6.6	CH3	H	CH3	852	H	O
6.7	CH3	H	CH3	853	H	O
6.8	CH3	H	CH3	854	H	O
6.9	CH3	H	CH3	855	H	O
6.10	CH3	H	CH3	856	H	O	203-205
6.11	CH3	H	CH3	857	H	S
6.12	CH3	H	CH3	858	H	O	200-202
6.13	CH3	H	CH3	859	H	S
6.14	CH3	H	CH3	860	H	O
6.15	CH3	H	CH3	861	H	O
6.16	CH3	H	CH3	862	H	O
6.17	CH3	H	CH3	863	H	O
6.18	CH3	H	CH3	864	H	O
6.19	CH3	H	CH3	865	H	O
6.20	CH3	H	CH3	866	H	O
6.21	CH3	H	CH3	867	H	O
6.22	CH3	H	CH3	868	H	O
6.23	CH3	H	CH3	869	H	O
6.24	CH3	H	CH3	870	H	O
6.25	CH3	H	CH3	871	H	O
6.26	CH3	H	CH3	872	H	S
6.27	CH3	H	CH3	873	H	O
6.28	CH3	H	CH3	874	H	O
6.29	CH3	H	CH3	875	H	O
6.30	CH3	H	CH3	876	H	O
6.31	CH3	H	CH3	877	H	O
6.32	CH3	H	CH3	878	H	O
6.33	CH3	H	CH3	879	H	O
6.34	CH3	H	CH3	880	H	O
6.35	CH3	H	CH3	881	H	O
6.36	CH3	H	CH3	882	H	O
6.37	CH3	H	CH3	883	H	O
6.38	CH3	H	CH3	884	H	O
6.39	CH3	H	CH3	885	H	O
6.40	CH3	H	CH3	886	H	O
6.41	Δ	H	CH3	887	H	O
6.42	Δ	H	CH3	888	H	S
6.43	Δ	H	CH3	889	H	O
6.44	Δ	H	CH3	890	H	O
6.45	Δ	H	CH3	891	H	O
6.46	Δ	H	CH3	892	H	O
6.47	Δ	H	CH3	893	H	O
6.48	Δ	H	CH3	894	H	O
6.49	Δ	H	CH3	895	H	O	resin; MS,
							1 H-NMR
6.50	Δ	H	CH3	896	H	S
6.51	Δ	H	CH3	897	H	O	resin; MS,
							1 H-NMR
6.52	Δ	H	CH3	898	H	S
6.53	Δ	H	CH3	899	H	O
6.54	Δ	H	CH3	900	H	O
6.55	Δ	H	CH3	901	H	O
6.56	Δ	H	CH3	902	H	O
6.57	Δ	H	CH3	903	H	O
6.58	Δ	H	CH3	904	H	S
6.61	Δ	H	CH3	905	H	O
6.60	Δ	H	CH3	906	H	O
6.61	Δ	H	CH3	907	H	O
6.62	Δ	H	CH3	908	H	O
6.63	Δ	H	CH3	909	H	O
6.64	Δ	H	CH3	910	H	O
6.65	Δ	H	CH3	911	H	O
6.66	Δ	H	CH3	912	H	O
6.67	Δ	H	CH3	913	H	O
6.68	Δ	H	CH3	914	H	O
6.69	Δ	H	CH3	915	H	O
6.70	CF2H	H	CH3	916	H	O
6.71	CF2H	H	CH3	917	H	S
6.72	CF2H	H	CH3	918	H	O
6.73	CF2H	H	CH3	919	H	O
6.74	CF2H	H	CH3	920	H	O
6.75	CF2H	H	CH3	921	H	O
6.76	CF2H	H	CH3	922	H	O
6.77	CF2H	H	CH3	923	H	O
6.78	CF2H	H	CH3	924	H	O
6.79	CF2H	H	CH3	925	H	S
6.80	CF2H	H	CH3	926	H	O
6.81	CF2H	H	CH3	927	H	S
6.82	CF2H	H	CH3	928	H	O
6.83	CF2H	H	CH3	929	H	O
6.84	CF2H	H	CH3	930	H	O
6.85	CF2H	H	CH3	931	H	O
6.86	CF2H	H	CH3	932	H	O
6.87	CF2H	H	CH3	933	H	S
6.88	CF2H	H	CH3	934	H	O
6.89	CF2H	H	CH3	935	H	O
6.90	CF2H	H	CH3	936	H	O
6.91	CF2H	H	CH3	937	H	O
6.92	CF2H	H	CH3	938	H	O
6.93	CF2H	H	CH3	939	H	O
6.94	CF2H	H	CH3	940	H	O
6.95	CF2H	H	CH3	941	H	O
6.96	CF2H	H	CH3	942	H	O
6.97	CF2H	H	CH3	943	H	O
6.98	CF2H	H	CH3	944	H	O

[0152]

TABLE 7
Compounds of the formula I, wherein A = A26 =
945
Compd.							Phys. data
No.	R1	R2	R3	R4	R5	X	[m.p.]
7.1	CH3	H	CH3	946	H	O
7.2	CH3	H	CH3	947	H	S
7.3	CH3	H	CH3	948	H	O
7.4	CH3	H	CH3	949	H	O
7.5	CH3	H	CH3	950	H	O
7.6	CH3	H	CH3	951	H	O
7.7	CH3	H	CH3	952	H	O
7.8	CH3	H	CH3	953	H	O
7.9	CH3	H	CH3	954	H	O
7.10	CH3	H	CH3	955	H	O
7.11	CH3	H	CH3	956	H	S
7.12	CH3	H	CH3	957	H	O
7.13	CH3	H	CH3	958	H	S
7.14	CH3	H	CH3	959	H	O
7.15	CH3	H	CH3	960	H	O
7.16	CH3	H	CH3	961	H	O
7.17	CH3	H	CH3	962	H	O
7.18	CH3	H	CH3	963	H	O
7.19	Δ	H	CH3	964	H	O
7.20	Δ	H	CH3	965	H	S
7.21	Δ	H	CH3	966	H	O
7.22	Δ	H	CH3	967	H	O
7.23	Δ	H	CH3	968	H	O
7.24	Δ	H	CH3	969	H	O
7.25	Δ	H	CH3	970	H	O
7.26	Δ	H	CH3	971	H	O
7.27	Δ	H	CH3	972	H	O
7.28	Δ	H	CH3	973	H	S
7.29	Δ	H	CH3	974	H	O
7.30	Δ	H	CH3	975	H	S
7.31	Δ	H	CH3	976	H	O
7.32	Δ	H	CH3	977	H	O
7.33	Δ	H	CH3	978	H	O
7.34	CF2H	H	CH3	979	H	O
7.35	CF2H	H	CH3	980	H	S
7.36	CF2H	H	CH3	981	H	O
7.37	CF2H	H	CH3	982	H	O
7.38	CF2H	H	CH3	983	H	O
7.39	CF2H	H	CH3	984	H	O
7.40	CF2H	H	CH3	985	H	O
7.41	CF2H	H	CH3	986	H	O
7.42	CF2H	H	CH3	987	H	O
7.43	CF2H	H	CH3	988	H	S
7.44	CF2H	H	CH3	989	H	O
7.45	CF2H	H	CH3	990	H	S
7.46	CF2H	H	CH3	991	H	O
7.47	CF2H	H	CH3	992	H	O
7.48	CF2H	H	CH3	993	H	O

[0153]

TABLE 8
Compounds of the formula I, wherein A = A27 =
994
Compd.							Phys. data
No.	R1	R2	R3	R4	R5	X	[m.p.]
8.1	CH3	H	CH3	995	H	O
8.2	CH3	H	CH3	996	H	S
8.3	CH3	H	CH3	997	H	O
8.4	CH3	H	CH3	998	H	O
8.5	CH3	H	CH3	999	H	O
8.6	CH3	H	CH3	1000	H	O
8.7	CH3	H	CH3	1001	H	O
8.8	CH3	H	CH3	1002	H	O
8.9	CH3	H	CH3	1003	H	O
8.10	CH3	H	CH3	1004	H	O
8.11	CH3	H	CH3	1005	H	S
8.12	CH3	H	CH3	1006	H	O
8.13	CH3	H	CH3	1007	H	S
8.14	CH3	H	CH3	1008	H	O
8.15	CH3	H	CH3	1009	H	O
8.16	CH3	H	CH3	1010	H	O
8.17	CH3	H	CH3	1011	H	O
8.18	CH3	H	CH3	1012	H	O
8.19	Δ	H	CH3	1013	H	O
8.20	Δ	H	CH3	1014	H	S
8.21	Δ	H	CH3	1015	H	O
8.22	Δ	H	CH3	1016	H	O
8.23	Δ	H	CH3	1017	H	O
8.24	Δ	H	CH3	1018	H	O
8.25	Δ	H	CH3	1019	H	O
8.26	Δ	H	CH3	1020	H	O
8.27	Δ	H	CH3	1021	H	O
8.28	Δ	H	CH3	1022	H	S
8.29	Δ	H	CH3	1023	H	O
8.30	Δ	H	CH3	1024	H	S
8.31	Δ	H	CH3	1025	H	O
8.32	Δ	H	CH3	1026	H	O
8.33	Δ	H	CH3	1027	H	O
8.34	CF2H	H	CH3	1028	H	O
8.35	CF2H	H	CH3	1029	H	S
8.36	CF2H	H	CH3	1030	H	O
8.37	CF2H	H	CH3	1031	H	O
8.38	CF2H	H	CH3	1032	H	O
8.39	CF2H	H	CH3	1033	H	O
8.40	CF2H	H	CH3	1034	H	O
8.41	CF2H	H	CH3	1035	H	O
8.42	CF2H	H	CH3	1036	H	O
8.43	CF2H	H	CH3	1037	H	S
8.44	CF2H	H	CH3	1038	H	O
8.45	CF2H	H	CH3	1039	H	S
8.46	CF2H	H	CH3	1040	H	O
8.47	CF2H	H	CH3	1041	H	O
8.48	CF2H	H	CH3	1042	H	O

[0154]

TABLE 9
Compounds of the formula I, wherein A = A31 =
1043
Compd.						Phys. data
No.	R1	R2	R3	R5	X	m.p. ° C.
9.1	CH3	H	CH3	H	O	resin, MS
9.2	CH3	H	CH3	H	S
9.3	CF2H	H	CH3	H	O
9.4	CF2H	H	CH3	H	S
9.5	CFH2	H	CH3	H	O
9.6	CFH2	H	CH3	H	S
9.7	Δ	H	CH3	H	O
9.8	Δ	H	CH3	H	S
9.9	Δ	H	CH2OCH3	H	O
9.10	Δ	H	CH2OCH3	H	S
9.11	CH2CH3	H	CH3	H	O	resin, MS

[0155]

TABLE 10
Compounds of formula I, wherein A = A33 =
1044
Compd.						Phys. data
No.	R1	R2	R3	R5	X	m.p. ° C.
10.1	CH3	H	CH3	H	O
10.2	CH2CH3	H	CH3	H	O
10.3	CF2H	H	CH3	H	O
10.4	CF2H	H	CH2OCH3	H	O
10.5	CF2CF3	H	CH3	H	O	168-169

[0156]

TABLE 11
Pyrrole carboxylic acid of the formula X
1045
(X), wherein R2 is hydrogen
	Compd.			Phys.data
	No.	R1	R3	m.p. ° C.
	11.1	CH3	CH3	166-168
	11.2	CH3	CH2CH3
	11.3	CH3	CHF2
	11.4	CH3	CH2OCH3
	11.5	CH3	CH2OCF3
	11.6	CHF2	CH3
	11.7	CHF2	CH2CH3
	11.8	CHF2	CH2OCH3
	11.9	CH2F	CH3
	11.10	CH2F	CH2CH3
	11.11	CH2F	CH2OCH3
	11.12	CH2CH3	CH3	164-165
	11.13	CH2CH3	CH2OCH3
	11.14	CF2CF3	CH3	180-181
	11.15	Δ	CH3	182-183
	11.16	Δ	CH2CH3
	11.17	Δ	CHF2
	11.18	Δ	CH2OCH3
	11.19	Δ	CH2OCF3
	11.20	CH2CH3	CH2CH3	68
	11.21	(CH3)2CH	CH3	158-159
	11.22	(CH3)2CH	CH2CH3	99-100

[0157]

TABLE 12
1                  H-NMR of selected compounds
Cmpd. No. 1                  H-NMR-data (ppm/multiplicity/number of H's); solvent = CDCl3
1.5       1.60-1.85/m/4H; 2.15-2.30/m/4H; 3.62/s/3H; 5.80/m/1H; 6.39/m/1H;
          6.95-7.15/m/3H; 7.20-7.30/m/1H; 7.94/s/1H; 8.46/d/1H
1.206     0.68-0.74/m/2H; 0.91-0.98/m/2H; 1.29-1.94/m/11H; 2.72/m/1H;
          3.55/s/3H; 6.36/m/1H; 7.13-7.34/m/4H; 7.75/m/1H; 8.19/s/1H(NH)
1.220     0.22-0.29/m/4H; 1.20/m/1H; 3.57/s/3H; 6.22/m/1H; 7.10-7.28/m/4H;
          7.32-7.45/m/4H; 8.15/s/1H; 8.35/d/1H
6.49      0.29/m/4H; 1.23/m/1H; 3.58/s/3H; 6.24/m/1H; 6.98-7.50/m/5H; 8.06/d/1H;
          8.15/m/2H(NH+1 pyridin-H); 8.42/d/1H
6.51      0.27/m/4H; 1.25/m/1H; 3.59/s/3H; 6.23/m/1H; 6.99-7.48/m/7H;
          8.15/s/1H; 8.42/d/1H;

FORMULATION EXAMPLES FOR COMPOUNDS OF FORMULA I

[0158] Working procedures for preparing formulations of the compounds of formula I such as Emulsifiable concentrates, Solutions, Granulates, Dusts and Wettable powders are described in WO 97/33890.

BIOLOGICAL EXAMPLES

Fungicidal Actions

Example B-1

Action Against Puccinia recondita/Wheat (Brownrust on Wheat)

[0159] 1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (1×105 uredospores/ml) on the test plants. After an incubation period of 2 days at 20° C. and 95% r. h. plants are kept in a greenhouse for 8 days at 20° C. and 60% r.h. The disease incidence is assessed 10 days after inoculation.

[0160] Compounds of Tables 1 to 10 show good activity in these tests. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy (<20% infestation).

Example B-2

Action Against Podosphaera leucotricha/Apple (Powdery Mildew on Apple)

[0161] 5 week old apple seedlings cv. McIntosh are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. One day after application apple plants are inoculated by shaking plants infected with apple powdery mildew above the test plants. After an incubation period of 12 days at 22° C. and 60% r. h. under a light regime of 14/10 h (light/dark) the disease incidence is assessed.

[0162] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-3

Action Against Venturia inaegualis/Apple (Scab on Apple)

[0163] 4 week old apple seedlings cv. McIntosh are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application apple plants are inoculated by spraying a spore suspension (4×105 conidia/ml) on the test plants. After an incubation period of 4 days at 21° C. and 95% r. h. the plants are placed for 4 days at 21° C. and 60% r. h. in a greenhouse. After another 4 day incubation period at 21° C. and 95% r. h. the disease incidence is assessed.

[0164] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-4

Action Against Eiysiphe graminis/Barley (Powdery Mildew on Barley)

[0165] 1 week old barley plants cv. Express are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application barley plants are inoculated by shaking powdery mildew infected plants above the test plants. After an incubation period of 6 days at 20° C./18° C. (day/night) and 60% r. h. in a greenhouse the disease incidence is assessed.

[0166] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-5

Action Against Botrtis cinerea/Apple (Botrytis on Apple Fruits)

[0167] In an apple fruit cv. Golden Delicious 3 holes are drilled and each filled with 30111 droplets of the formulated test compound (0.002% active ingredient). Two hours after application 5041 of a spore suspension of B. cinerea (4×105 conidia/ml) are pipetted on the application sites. After an incubation period of 7 days at 22° C. in a growth chamber the disease incidence is assessed.

[0168] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-6

[0169] Action Against Botrytis cinerea/Grape (Botrytis on Grapes)

[0170] 5 week old grape seedlings cv. Gutedel are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application grape plants are inoculated by spraying a spore suspension (1×106 conidia/ml) on the test plants. After an incubation period of 4 days at 21° C. and 95% r. h. in a greenhouse the disease incidence is assessed.

[0171] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-7

Action Against Botrytis cinerea/Tomato (Botrytis on Tomatoes)

[0172] 4 week old tomato plants cv. Roter Gnom are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application tomato plants are inoculated by spraying a spore suspension (1×105conidia/ml) on the test plants. After an incubation period of 4 days at 20° C. and 95% r. h. in a growth chamber the disease incidence is assessed.

[0173] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-8

Action Against Pyrenophora teres/Barley (Net Blotch on Barley)

[0174] 1 week old barley plants cv. Express are treated with the formulated test compound (0.002% active ingredient) in a spray chamber. Two days after application barley plants are inoculated by spraying a spore suspension (3×104 conidia/ml) on the test plants. After an incubation period of 2 days at 20° C. and 95% r. h. plants are kept for 2 days at 20° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 4 days after inoculation.

[0175] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Example B-9

Action Against Septoria nodorum/Wheat (Septoria Leaf Spot on Wheat)

[0176] 1 week old wheat plants cv. Arina are treated with the formulated test compound (0.02% active ingredient) in a spray chamber. One day after application wheat plants are inoculated by spraying a spore suspension (5×106 conidia/ml) on the test plants. After an incubation period of 1 day at 20° C. and 95% r. h. plants are kept for 10 days at 20° C. and 60% r.h. in a greenhouse. The disease incidence is assessed 11 days after inoculation.

[0177] Compounds of Tables 1 to 10 show good activity in this test. The compounds 1.5, 1.9, 1.23, 1.25, 1.46, 1.144, 1.153, 1.183, 1.187, 1.190, 1.192, 1.206, 1.244, 1.260, 1.261, 1.265, 1.266, 1.268, 1.269, 1.271, 1.272, 2.23, 2.190, 2.192, 4.12, 6.10, 6.12, 6.49, 6.51 and 10.5 exhibit strong efficacy.

Claims

1. A pyrrolecarboxamide or pyrrolethioamide of the formula I

2. A compound of formula I according to claim 1, wherein R1 is C1-C4alkyl; C1-C4haloalkyl; C1-C4alkoxy-C1-C4alkyl; C1-C4haloalkoxy-C1-C4alkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl or halogen; or halogen; R2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy, C1-C4haloalkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, cyano or halogen; R3 is C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy-C1-C4alkyl or C1-C4haloalkoxy-C1-C4alkyl; A is a group 1047104810491050and R4 is C3-C7cycloalkyl, C4-C7cycloalkenyl, C5-C7cycloalkadienyl wherein the cycloalkyl group can be mono- to pentasubstituted by halogen, hydroxy, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C4alkenyl, C2-C5alkynyl, C1-C4haloalkyl; phenyl unsubstituted or substituted by halogen, nitro, cyano, CHO, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkoxy, C2-C5alkenyl, C2-C5alkynyl, C1-C4haloalkyl, COOC1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4alkyl-C1-C4alkoxy, C1-C4haloalkoxy-C1-C4alkyl, C1-C4haloalkyl-C1-C4alkoxy; thienyl, furyl, pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, imidazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C6haloalkyl, C1-C6alkyl, C2-C5alkenyl, C2-C5alkynyl nitro, cyano, hydroxy, CHO, C1-C6alkoxy, COOC1-C6alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl or C1-C6haloalkoxy; R5 is hydrogen, cyano, nitro, halogen, C1-C4haloalkyl, C1-C4alkyl, C1-C4alkoxy-C1-C4alkyl, C1-C4haloalkoxy-C1-C4alkyl, C1-C4alkoxy or C1-C4haloalkoxy; R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, halogen, C1-C4haloalkyl, C1-C4alkyl, C2-C5alkenyl, C2-C5alkynyl, C1-C4alkoxy, C1-C4alkoxy-C1-C4alkyl, C1-C6haloalkoxy-C1-C4alkyl, C1-C4haloalkoxy or C3-C7cycloalkyl.

3. A compound of formula I according to claim 2, wherein X is oxygen.

4. A compound of formula I according to claim 2, wherein X is sulfur.

5. A compound of formula I according to claim 3, wherein R1 is C1-C3alkyl; C1-C3haloalkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C3alkyl, C1-C3haloalkyl or halogen; R2 is hydrogen, C1-C4alkyl or C1-C4haloalkyl; R3 is C1-C4alkyl, C1-C3haloalkyl or C1-C3alkoxy-C1-C3alkyl; A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31 or A32; R4 is C5-C7cycloalkyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C1-C7cycloalkenyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cyclodialkenyl, unsubstituted or mono- to disubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; thienyl, furyl, isoxazolyl, oxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, which are unsubstituted or substituted by halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; R5 is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; and R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy.

6. A compound of formula I according to claim 5, wherein A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27 or A31; R1 is C1-C2alkyl, C1-C3haloalkyl or cyclopropyl; R2 is hydrogen or C1-C3alkyl; R3 is C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl; R4 is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C1-C2alkyl, C1-C2haloalkyl or C1-C2haloalkoxy; thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4haloalkoxy; R5 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy or C1-C3haloalkoxy; and R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen or C1-C3alkyl.

7. A compound of formula I according to claim 6, wherein R1 is methyl, ethyl, CFH2 or CF2H; R2 is hydrogen; R3 is methyl or CH2OCH3; A is A31 or A33; and R4 is halophenyl, C5-C7cycloalkyl or halothienyl.

8. A compound of formula I according to claim 4, wherein R1 is C1-C3alkyl; C1-C3haloalkyl; C3-C6cycloalkyl unsubstituted or substituted by C1-C3alkyl, C1-C3haloalkyl or halogen; R2 is hydrogen, C1-C4alkyl or C1-C4haloalkyl; R3 is C1-C4alkyl, C1-C3haloalkyl or C1-C3alkoxy-C1-C3alkyl; A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31 or A32; R4 is C5-C7cycloalkyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cycloalkenyl, unsubstituted or mono- to trisubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkoxy, C1-C4haloalkoxy or C1-C4alkoxy; C5-C7cyclodialkenyl, unsubstituted or mono- to disubstituted by halogen, hydroxy, C2-C4alkenyl, C2-C4alkynyl, C1-C4alkyl, C1-C4haloalkyl, C1-C4haloalkoxy or C1-C4alkoxy; thienyl, furyl, isoxazolyl, oxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, which are unsubstituted or substituted by halogen, hydroxy, C1-C4alkyl, C1-C4haloalkyl, C1-C4alkoxy or C1-C4haloalkoxy; phenyl which is unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; R5 is hydrogen, halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy; and R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen, C1-C4alkyl, C1-C4alkoxy, C1-C4haloalkyl or C1-C4haloalkoxy.

9. A compound of formula I according to claim 8, wherein A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27 or A31; R1 is C1-C2alkyl, C1-C3haloalkyl or cyclopropyl; R2 is hydrogen or C1-C3alkyl; R3 is C1-C3alkyl or C1-C3alkoxy-C1-C3alkyl; R4 is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C1-C2alkyl, C1-C2haloalkyl or C1-C2haloalkoxy; thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C1-C4alkyl, C1-C4haloalkyl or C1-C4haloalkoxy; R5 is hydrogen, halogen, C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy or C1-C3haloalkoxy; and R6, R7, R8, R9 and R10 are identical or different and are each independently of the others hydrogen or C1-C3alkyl.

10. A process for the preparation of compounds of formula I which comprises reacting the starting materials according to the scheme

11. A composition for controlling microorganisms and preventing attack and infestation of plants therewith, wherein the active ingredient is a compound as claimed in claim 1 together with a suitable carrier.

12. Use of a compound of formula I according to claim 1 for protecting plants against infestation by phytopathogenic microorganisms.

13. A method of controlling or preventing infestation of cultivated plants by phytopathogenic microorganisms by application of a compound of formula I as claimed in claim 1 to plants, to parts thereof or the locus thereof.

14. A pyrrole carboxylic acid of formula X