Trifluoromethylpyrrole carboxamides and...

Details Trifluoromethylpyrrole carboxamides and... Trifluoromethylpyrrole carboxamides and...

2002-10-08

2004-03-02

Lambkin, Deborah C. (Department: 1626)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S527000

Reexamination Certificate

active

06699818

ABSTRACT:

This application is a 371 of PCT/EP00/1196 filed Nov. 11, 2000.
The present invention relates to novel trifluoromethylpyrrolcarboxamides or trifluoromethylpyrrolethioamides 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 trifluoromethylpyrrolcarboxamides of the present invention have the general formula I
wherein
X is oxygen or sulfur;
R
1
is hydrogen, C
1
-C
4
alkyl unsubstituted or substituted, C
1
-C
4
alkoxy unsubstituted or substituted, or halogen;
R
2
is C
1
-C
4
alkyl unsubstituted or substituted; and
A is orthosubstituted aryl; orthosubstituted heteroaryl; bicydoaryl unsubstituted or substituted; or bicycdoheteroaryl 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 mites 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, haloakyl, 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, habalkoxy, 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.
Aryl is phenyl or naphthyl.
Heteroaryl will be understood as a 5- to 10membered 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, tniadiazblyl, triazol, tefazoly, pyrrolyl, dithiolyl, oxathio, dioxazolyl, oxathlazolyl, oxathlolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, tiazinyl, indolyl, benzoluranyl, beimkidazolyl, indazolyl, benzotazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxafinyl, quinazolinyl, cinnolinyl, naphthdinyl, isobebzofuranyl, isoindomy, benzothiadiazol, benotienyl, benzisoxazolyl, purinyl, 5,6-dihydro-1,4,2-dioxazinyl, and the like.
Bicydoaryl or bicycloheteroaryl will be understood as a 6-membered aryl or 6-membered heteroaryl, 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, may be a ring from 5 to 7 ring members, of which up to 3 memnbers may be heteroatoms selected from the group nitrogen, oxygen and sulfur. The following list of examples is not exhaustive: dihydroisobenzofuranyl, dihydroisoindolyl, and the like.
Preferred embodiments of compounds of the formula I are those wherein
X is oxygen or sulfur; or
X is oxygen; or
X is sulfur; or
R
1
is hydrogen, C
1
-C
4
alkyl unsubstituted or substituted, C
1
-C
4
alkoxy unsubstituted or substituted, or halogen; or
R
1
is hydrogen, C
1
-C
4
alkyl C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy,
C
1
-C
4
aloalkoxy, C
1
-C
4
haloalkoxy-C
1
-C
4
alkyl or halogen; or
R
1
is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; or
R
1
is hydrogen or C
1
-C
3
alkyl; or
R
2
is C
1
-C
4
alkyl unsubstituted or substituted; or
R
2
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
2
is C
1
-C
4
alkyl, C
1
-C
3
haloalkyl; or C
1
-C
3
alkoxy-C
1
-C
3
alkyl; or
R
2
is C
1
-C
3
alkyl or C
1
-C
3
alkoxy-C
1
-C
3
alkyl; or
A is orthosubstituted aryl; orthosubstituted heteroaryl; bicydoaryl unsubstituted or substituted; or bicycloheteroaryl unsubstituted or substituted; or
A is a group
A is A1, A2, A3, A5, A8, A10, A13, A14, A17, A18, A20, A21, A22, A23, A24, A25, A26, A27, A29, A31or A32; or
A is A1, A2, A3, A17, A20, A21, A24, A25, A26, A27 or A31; or
R
3
is C
3
-C
7
cycloalkyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
C
4
haloalkoxy or C
1
-C
4
alkyl; C
4
-C
7
cycloalkenyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloakyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
C
4
haloalkoxy or C
1
-C
4
alkyl; C
6
-C
7
cyclodialkenyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
haloalkoxy or C
1
-C
4
alkyl; thienyl, furyl, pyrrolyl pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, tniadiazblyl, imidazolyl, tetrazolyl, tiazlnyl, benotienyl, 5,6dihydro-1,4,2-dioxazinyl, pyridyl, pyrazlnyl, pyridazinyl or pyrimidinyl, which are unsubstituted or substituted by halogen, C
1
-C
4
haloalkyl, C
1
-C
8
alkyl, hydroxy, cyano, nitro, CHO, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, COOC
1
-C
4
alkyl, C
1
-C
8
haloalkoxy-C
1
-C
4
alkyl, C
1
-C
8
alkoxy or C
1
-C
8
haloalkoxy; or
R
3
is C
5
-C
7
cycloalkyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
3
alkoxy or C
1
-C
4
alkyl; C
5
C
7
cycloalkenyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
1
-C
3
alkoxy, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl or C
1
-C
4
alkyl; C
6
-C
7
cyclodialkenyl unsubstituted or mono- to trisubstituted by halogen, hydroxy, C
1
-C
3
alkoxy, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl or C
1
-C
3
alkyl; thienyl, furyl, oxazolyl, isoxazolyl, thiadiazolyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl, which are unsubstituted or substituted by halogen, C
1
-C
4
haloalkyl, C
1
-C
4
alkyl, hydroxy, C
1
-C
4
alkoxy or C
1
C
4
haloalkoxy; or
R
3
is cyclohexyl, cyclohexenyl or cyclohexadienyl, which are unsubstituted or mono- to disubstituted by chloro, bromo, C
1
-C
2
alkyl C
1
-C
2
haloalkyl or C
1
-C
2
haloalkoxy, thienyl, furyl, triazinyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl which are unsubstituted or substituted by halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or C
1
-C
4
haloalkoxy; or
R
31
is C
3
-C
7
cycloalkyl, C
3
-C
07
cycloalkenyl or C
5
-C
7
cyloalkadienyl which are unsubstituted or substituted by halogen, C
1
-C
6
alkoxy, C
1
-C
6
alkoxy-C
1
-C
6
alkyl, C
1
-C
6
haloalkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy, C
2
-C
4
alkenyl or C
2
-C
3
alkynyl; phenyl unsubstituted or substituted by halogen, C
1
-C
6
alkoxy, C
1
-C
6
aloalkoxy, C
1
-C
4
alkyl, C
1
-C
4
haloakyl, C
2
C
4
alkenyl, C
2
-C
5
alkynyl, CHO, 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, cyano or nitro; thienyl, furyl, pyrrolyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, thiadiazolyl, imidazolyl, triazinyl, pyridyl, pyridazinyl, pyrazinyl or pyrimidinyl, which are unsubstituted or substituted by halogen, C
1
-C
6
haloalkyl, C
1
-C
6
alkyl, hydroxy, cyano, nitro, CHO, COOC
1
-C
4
alkyl, C
1
-C
6
haloalkoxy-C
4
-C
4
alkyl, C
1
C
4
alkoxy-C
1
-C
4
al

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