Pyrrolecarboxamides and pyrrolethioamides as fungicides

Details Pyrrolecarboxamides and pyrrolethioamides as fungicides Pyrrolecarboxamides and pyrrolethioamides as fungicides

2002-10-08

2004-10-19

McKane, Joseph K. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S537000

Reexamination Certificate

active

06806286

ABSTRACT:

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.
The pyrrolecarboxamides (thioamides) of the present invention have the general formula I
wherein
X is oxygen or sulfur;
R
1
is C
1
-C
4
alkyl unsubstituted or substituted, with the exception of CF
3
; C
3
-C
6
cycloalkyl unsubstituted or substituted; or halogen;
R
2
is hydrogen, C
1
-C
4
alkyl unsubstituted or substituted, C
1
-C
4
alkoxy unsubstituted or substituted, cyano or halogen;
R
3
is C
1
-C
4
alkyl unsubstituted or substituted; and
A is orthosubstituted aryl; orthosubstituted heteroaryl; bicycloaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted.
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.
Where asymmetrical carbon atoms are present in the compounds of formula I, 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.
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. 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. Haloalkoxy is a monohalogenated to perhalogenated alkoxy radical, such as, inter alia, OCH
2
F, OCHF
2
, OCF
3
, OCHFCH
3
, OCH
2
CH
2
Br, OCF
2
CHFCl.
Substituted alkyl will be understood as for example haloalkyl, alkoxy-alkyl, haloalkoxy-alkyl.
Cycloalkyl is, depending on the ring size, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl. Substituted cycloalkyl will be understood for example as alkyl-cyloalkyl, haloalkyl-cycloalkyl, alkoxy-cyloalkyl, haloalkoxy-cyloalkyl, halo-cyloalkyl, alkoxyalkyl-cycloalkyl, haloalkoxyalkyl-cycloalkyl.
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.
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.
Aryl is phenyl or naphthyl.
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.
Bicycloaryl or bicycdoheteroaryl will be understood as a 6-membered aryl or 6membered 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.
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.
Preferred embodiment of compounds of formula I are those wherein
X is oxygen or sulfur, or
X is oxygen; or
X is sulfur, or
R
1
is C
1
-C
4
alkyl unsubstituted or substituted, with the exception of CF
3
; C
3
-C
6
cycloalkyl unsubstituted or substituted; or halogen; or
R
1
is C
1
-C
4
alkyl; C
1
-C
4
haloalkyl; C
1
-C
4
alkoxy-C
1
-C
4
alkyl; C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl; C
3
-C
6
cycloalkyl unsubstituted or substituted by C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl or halogen; or halogen; or
R
1
is C
1
-C
3
alkyl; C
1
-C
3
haloalkyl; C
3
-C
6
cycloalkyl unsubstituted or substituted by C
1
-C
3
alkyl, C
1
-C
3
haloalkyl or halogen; or
R
1
is C
1
-C
2
alkyl, C
1
-C
3
haloalkyl or cyclopropyl; or
R
1
is methyl, ethyl, CFH
2
or CF
2
H; or
R
2
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl, cyano or halogen; or
R
2
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; or
R
2
is hydrogen or C
1
-C
3
alkyl; or
R
2
is hydrogen; or
R
3
is C
1
-C
4
alkyl unsubstituted or substituted; or
R
3
is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl or C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl; or
R
3
is C
1
-C
4
alkyl, C
1
-C
3
haloalkyl or C
1
-C
3
alkoxy-C
1
-C
3
alkyl; or
R
3
is C
1
-C
3
alkyl or C
1
-C
3
alkoxy-C
1
-C
3
alkyl; or
R
3
is methyl or CH
2
OCH
3
; or
A is orthosubstituted aryl; orthosubstituted heteroaryl; bicycloaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted; or
A is a group
 or
A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A24, A25, A26, A27, A29, A31, A32 or A33; or
A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27, A31 or A33; or
A is A31 or A33; or
R
4
is C
3
-C
7
cycloalkyl, C
4
-C
7
cycloalkenyl, C
5
-C
7
cyloalkadienyl wherein the cycloalkyl group can be mono- to pentasubstituted by halogen, hydroxy, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
2
-C
4
alkenyl, C
2
-C
5
alkynyl, C
1
-C
4
haloalkyl; phenyl unsubstituted or substituted by halogen, nitro, cyano, CHO, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
2
-C
5
alkenyl, C
2
-C
5
alkynyl, C
1
-C
4
haloalkyl, COOC
1
—C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkyl-C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl, C
1
-C
4
haloalkyl-C
1
-C
4
alkoxy; pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, imidazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C
1
-C
6
halo

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