Microbicidal N-sulfonylglycin alkynyloxyphenethyl amide...

Details Microbicidal N-sulfonylglycin alkynyloxyphenethyl amide... Microbicidal N-sulfonylglycin alkynyloxyphenethyl amide...

2000-02-04

2002-11-19

Chang, Ceila (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Nitrogen containing other than solely as a nitrogen in an...

C514S247000, C514S248000, C514S249000, C514S256000, C514S299000, C514S307000, C514S311000, C514S357000, C514S364000, C514S365000, C514S367000, C514S374000, C514S378000, C514S394000, C514S400000, C514S406000, C514S415000, C514S427000, C514S438000, C514S443000, C514S469000, C514S473000, C514S600000, C514S605000, C544S224000, C544S237000, C544S257000, C544S335000, C544S353000, C546S122000, C546S146000, C546S172000, C546S332000, C546S337000, C548S131000, C548S178000, C548S204000, C548S217000, C548S236000, C548S

Reexamination Certificate

active

06482859

ABSTRACT:

The present invention relates to novel a-amino acid derivatives of formula I below. It relates to the preparation of those substances and to agrochemical compositions comprising at least one of those compounds as active ingredient. The invention relates also to the preparation of the said compositions and to the use of the compounds or of the compositions in controlling or preventing the infestation of plants by phytopathogenic microorganisms, especially fungi.
The invention relates to compounds of the general formula I
as well as possible isomers and mixtures of isomers thereof,
wherein
n is a number zero or one; and
R
1
is C
1
-C
12
alkyl that is unsubstituted or may be substituted by C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfonyl, C
3
-C
8
cycloalkyl, cyano, C
1
-C
6
alkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl or by C
3
-C
6
alkynyloxycarbonyl; C
3
-C
8
cycloalkyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl; or a group NR
11
R
12
wherein R
11
and R
12
are each independently of the other hydrogen or C
1
-C
6
alkyl, or together are tetra- or penta-methylene;
R
2
and R
3
are each independently of the other hydrogen; C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
alkylthio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
3
-C
8
cycloalkyl; C
3
-C
8
cycloalkyl; C
1
-C
4
alkyl; or the two groups R
2
and R
3
together with the carbon atom to which they are bonded form a three- to eight-membered ring;
R
4
, R
5
, R
6
and R
7
are identical or different and are each independently of the others hydrogen or C
1
-C
4
alkyl;
R
8
is C
1
-C
6
alkyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl;
A is C
1
-C
6
alkylene; and
B is optionally mono- or poly-nuclear, unsubstituted or substituted aryl; optionally mono- or poly-nuclear, unsubstituted or substituted heteroaryl; C
4
-C
12
alkyl; or C
3
-C
8
cycloalkyl.
Examples of aryl in the above-mentioned sense are:
phenyl, naphthyl, anthracenyl, phenanthrenyl.
Examples of heteroaryl are:
furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl, naphthyridinyl.
Examples of substituents of those aryl or heteroaryl groups are:
alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl, phenyl-alkyl, it being possible for those groups to carry one or more identical or different halogen atoms; alkoxy; alkenyloxy; alkynyloxy; alkoxyalkyl; haloalkoxy, alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; alkynyloxycarbonyl.
In the above formula I, “halogen” includes fluorine, chlorine, bromine and iodine.
The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched, and this applies also to the alkyl, alkenyl or alkynyl moiety of other alkyl-, alkenyl- or alkynyl-containing groups.
Depending upon the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be understood as being, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl and the isomers thereof, for example isopropyl, isobutyl, tert-butyl or sec-butyl, isopentyl or tert-pentyl. Cycloalkyl is, depending upon the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
Depending upon the number of carbon atoms mentioned, alkenyl as a group or as a structural element of other groups is to be understood as being, for example, ethenyl, allyl, buten-2-yl, buten-3-yl, penten-1-yl, penten-3-yl, hexen-1-yl, 4-methyl-3-pentenyl or 4-methyl-3-hexenyl.
Alkynyl as a group or as a structural element of other groups is, for example, ethynyl, propyn-1-yl, propyn-2-yl, butyn-1-yl, butyn-2-yl, 1-methyl-2-butynyl, hexyn-1-yl, 1-ethyl-2-butynyl, octyn-1-yl.
A haloalkyl group may have one or more (identical or different) halogen atoms, for example CHCl
2
, CH
2
F, CCl
3
, CH
2
Cl, CHF
2
, CF
3
, CH
2
CH
2
Br, C
2
Cl
5
, CH
2
Br, CHClBr, CF
3
CH
2
, etc.
The presence of at least one asymmetric carbon atom and/or at least one asymmetric sulfur atom in the compounds of formula I means that the compounds may occur in optically isomeric forms. As a result of the presence of a possible aliphatic C═C double bond, geometric isomerism may also occur. Formula I is intended to include all those possible isomeric forms and mixtures thereof.
Preference is given to compounds of formula I wherein
R
1
is C
1
-C
12
alkyl; C
3
-C
8
cycloalkyl; C
2
-C
12
alkenyl; C
2
-C
12
alkynyl; C
1
-C
12
haloalkyl; or a group NR
11
R
12
wherein R
11
and R
12
are each independently of the other hydrogen or C
1
-C
6
alkyl, or together are tetra- or penta-methylene;
R
2
is hydrogen;
R
3
is C
1
-C
8
alkyl; C
1
-C
8
alkyl substituted by hydroxy, C
1
-C
4
alkoxy, mercapto or by C
1
-C
4
alkyl-thio; C
3
-C
8
alkenyl; C
3
-C
8
alkynyl; C
3
-C
8
cycloalkyl; or C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl;
B is phenyl; naphthyl; or heteroaryl that is formed from one or two five- or six-membered rings and that may contain from 1 to 4 identical or different hetero atoms selected from nitrogen, oxygen and sulfur; wherein the phenyl, naphthyl or heteroaryl may optionally carry from 1 to 5 identical or different substituents selected from:
C
1
-C
8
alkyl, C
2
-C
28
alkenyl, C
2
-C
8
alkynyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cycloalkyl-C
1
-C
4
alkyl, phenyl, phenyl-C
1
-C
4
alkyl, those groups being unsubstituted or mono- to per-halogenated and the halogen atoms being identical or different; C
1
-C
8
alkoxy; C
3
-C
8
alkenyloxy; C
3
-C
8
alkynyloxy; C
1
-C
4
alkoxy-C
1
-C
4
alkyl; C
1
-C
8
haloalkoxy; C
1
-C
8
alkylthio; C
1
-C
8
haloalkylthio; C
1
-C
8
alkyl-sulfonyl; formyl; C
2
-C
8
alkanoyl; hydroxy; halogen; cyano; nitro; amino; C
1
-C
8
alkylamino; C
1
-C
8
dialkylamino; carboxy; C
1
-C
8
alkoxycarbonyl; C
3
-C
8
alkenyloxycarbonyl; and C
3
-C
8
alkynyloxycarbonyl (sub-group A).
Within the scope of sub-group A, special mention should be made of those compounds of formula I wherein
R
1
is C
1
-C
6
alkyl; C
5
-C
6
cycloalkyl; C
2
-C
6
alkenyl; C
1
-C
6
haloalkyl; or a group NR
11
R
12
wherein
R
11
and R
12
are each independently of the other hydrogen or C
1
-C
6
alkyl;
R
3
is C
1
-C
8
alkyl; or C
3
-C
6
cycloalkyl;
R
4
is hydrogen or C
1
-C
4
alkyl;
R
5
, R
6
and R
7
are hydrogen;
R
8
is C
1
-C
6
alkyl;
A is C
1
-C
2
alkylene; and
B is phenyl, naphthyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyi, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, benzothiazolyl or benzoxazolyl, each unsubstituted or substituted by from 1 to 5 substituents selected from: C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
3
-C
8
cycloalkyl, C
3
-C
8
-cycloalkyl-C
1
-C
4
alkyl, phenyl, phenyl-C
1
-C
4
alkyl, those groups being unsubstituted or mono- to per-halogenated and the halogen atoms being identical or different; C
1
-C
8
alkoxy; C
3
-C
8
-alkenyloxy; C
3
-C
8
alkynyloxy; C
1
-C
4
alkoxy-C
1
-C
4
alkyl; C
1
-C
8
haloalkoxy; C
1
-C
8
alkylthio; C
1
-C
8
-haloalkylthio; C
1
-C
8
alkylsulfonyl; formyl; C
2
-C
8
alkanoyl; hydroxy; halogen; cyano; nitro; amino; C
1
-C
8
alkylamino; C
1
-C
8
dialkylamino; carboxy; C
1
-C
8
alkoxycarbonyl; C
3
-C
8
alkenyl-oxycarbonyl; and C
3
-C
8
alkynyloxycarbonyl (sub-group B).
Within the scope of sub-group B, special preference is given to a group of compounds of formula I wherein
n is the number one;
R
1
is C
1
-C
6
alkyl; C
1
-C
6
haloalkyl; or a group NR
11
R
12
wherein R
11
and R
12
are each independently of the other C
1
-C
4
alkyl;
R
3
is C
3
-C
4
alkyl; or cyclopropyl;
R
4
is hydrogen or methyl;
R
8
is C
1
-C
2
alkyl;
A is methylene; and
B is phenyl

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