Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-08-24
2001-08-21
Raymond, Richard L. (Department: 1611)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S247000, C514S249000, C514S256000, C514S299000, C514S307000, C514S311000, C514S357000, C514S364000, C514S365000, C514S367000, C514S374000, C514S378000, C514S394000, C514S400000, C514S406000, C514S415000, C514S427000, C514S438000, C514S443000, C514S469000, C514S473000, C514S600000, C514S601000, C514S605000, C544S224000, C544S237000, C544S257000, C544S335000, C544S353000, C546S122000, C546S146000, C546S172000, C546S332000, C546S337000, C548S131000, C548S178000, C548S204000, C548S217000, C548S236000, C548S
Reexamination Certificate
active
06277849
ABSTRACT:
The present invention relates to novel a-amino acid derivatives of the 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 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, C
1
-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, 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 wherein 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;
p is a number zero or one;
R
9
is C
1
-C
6
alkylene; and
A is unsubstituted or mono- or poly-substituted heteroaryl;
unsubstituted or mono- or poly-substituted aryl containing more than 6 carbon atoms.
Examples of aryl in the above-mentioned sense are:
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 and the isomers thereof, for example isopropyl, isobutyl, tert-butyl or sec-butyl. Cycloalkyl is, depending upon the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
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 etc.
Preference is given to compounds of formula I wherein
A is naphthyl, 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 that naphthyl or heteroaryl may carry from 1 to 4 identical or different 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, it being possible for the hydrogen atoms of those groups to have been replaced by one or more identical or different halogen atoms; 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
alkoxy-carbonyl, C
3
-C
8
alkenyloxycarbonyl and C
3
-C
8
alkynyloxycarbonyl (sub-group A).
Within the scope of subgroup A, special mention should be made of those compounds of formula I wherein
A is naphthyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, quinoxatinyl, unsubstituted or substituted by from 1 to 3 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, it being possible for the hydrogen atoms of those groups to have been replaced by one or more identical or different halogen atoms; 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
alkenyloxycarbonyl and C
3
-C
8
alkynyloxycarbonyl (subroup B).
Within the scope of subgroup B, special preference is given to a group of compounds of formula I wherein
p is a number one;
A is naphthyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzothiophenyl, benzofuranyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, quinoxalinyl, unsubstituted or substituted by from 1 to 3 substituents selected from:
C
1
-C
8
alkyl, C
1
-C
8
haloalkyl, phenyl, phenyl-C
1
-C
4
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
haloalkoxy, C
1
-C
8
alkylthio, C
1
-C
8
haloalkylthio, halogen, cyano and nitro (sub-group Ca).
A special group within the scope of sub-group Ca comprises compounds of formula I wherein
R
9
is —CH
2
—;
A is naphthyl, furyl, thienyl, thiazolyl, oxazolyl, pyridyl. pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, unsubstituted or substituted by from 1 to 3 substituents selected from:
C
1
-C
8
alkyl, C
1
-C
8
haloalkyl, phenyl, phenyl-C
1
-C
4
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
haloalkoxy, C
1
-C
8
alkylthio, C
1
-C
8
haloalkylthio, halogen, cyano and nitro (sub-group Cb).
Another especially preferred group within the scope of sub-group B comprises compounds of formula I wherein
n is a number one,
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
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, 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
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 (sub-group Da).
Within group Da, preference is given to compounds of formula I wherein
R
1
is C
1
-C
12
alkyl, C
1
-C
12
haloalkyl or a group NR
11
R
12
; wherein R
11
and R
12
are each independently of the other C
1
-C
6
alkyl;
R
3
is C
1
-C
8
alkyl;
R
4
is hydrogen or C
1
-C
4
alkyl;
R
5
, R
6
and R
7
are hydrogen;
R
8
is C
1
Raymond Richard L.
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
LandOfFree
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