N-sulphonyl and N-sulphinyl phenylglycinamide

Details N-sulphonyl and N-sulphinyl phenylglycinamide N-sulphonyl and N-sulphinyl phenylglycinamide

2000-08-25

2002-05-21

O'Sullivan, Peter (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S347000, C514S367000, C514S415000, C514S424000, C514S445000, C514S459000, C514S471000, C514S552000, C514S604000, C514S605000, C514S607000, C514S539000, C514S542000, C560S013000, C546S265000, C549S065000, C549S419000, C549S494000, C558S413000

Reexamination Certificate

active

06391918

ABSTRACT:

This application is a 371 of international application PCT/EP99/01216, filed Feb. 25, 1999.
The present invention relates to novel &agr;-amino acid amides of formula I below. It relates to the preparation of those substances and to agrochemical compositions that comprise at least one of those compounds as active ingredient. The invention also relates to the preparation of the said compositions and to the use of the active ingredients or the compositions in the control or prevention of plant infestation by phytopathogenic microorganisms especially fungi.
The compounds according to the invention correspond to the general formula I
as well as possible isomers and mixtures of isomers thereof,
wherein the substituents are defined as follows:
n is the number zero or one;
R
1
is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl; or a group NR
a
R
b
wherein R
a
and R
b
are each independently of the other hydrogen, alkyl or form together an alkylene bridge;
R
2
is hydrogen or alkyl;
R
3
is optionally substituted aryl or heteroaryl;
A is alkylene; and
B is optionally substituted aryl;
with the exception of the following compounds
2-phenyl-N-(1-phenyl-ethyl)-2-(4-methylphenyl)-sulfonylamino-acetamide,
2-phenyl-N-(1-phenyl-ethyl)-2-(4-chlorophenyl)-sulfonylamino-acetamide,
2-phenyl-N-(1-phenyl-ethyl)-2-(4-nitrophenyl)-sulfonylamino-acetamide,
2-phenyl-N-(1-phenyl-ethyl)-2-(4-methoxyphenyl)-sulfonylamino-acetamide,
2-phenyl-N-(1-phenyl-ethyl)-2-(4-fluorophenyl)-sulfonylamino-acetamide,
2-phenyl-N-(1-phenyl-ethyl)-2-phenyl-sulfonylamino-acetamide and
2-phenyl-N-(1-phenyl-ethyl)-2-methane-sulfonylamino-acetamide.
The above alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl or heteroaryl groups may carry one or more identical or different substituents. Normally not more than five substituents in each of these groups are present at the same time. Examples of substituents of these groups are: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, phenyl and phenylalkyl, it being possible in turn for all of the preceding 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, preferably fluorine, chlorine or bromine.
The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched, this applying also to the alkyl, alkenyl or alkynyl moiety of other groups containing alkyl, alkenyl or alkynyl.
Depending on the number of carbon atoms mentioned, alkyl on its own or as part of another substituent is to be understood as meaning, for example, methyl, ethyl, propyl, butyl, pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl and the isomers thereof, such as isopropyl, isobutyl, tert-butyl, sec-butyl, tert-amyl, 1-ethyl-hexyl, n-octyl, n-nonyl or n-decyl. Cycloalkyl denotes, depending on the number of carbon atoms mentioned, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl.
Alkenyl will be understood as meaning straight-chain or branched alkenyl such as allyl, vinyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pent-2-en-1-yl or hex-2-en-1-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-2-yl-1-yl, but-1-yn-3-yl, pent-2-yn-1-yl or hex-2-yn-1-yl. The preferred meaning is propargyl.
A haloalkyl group may have one or more (identical or different) halogen atoms, such as, for example, CHCl
2
, CH
2
F, CCl
3
, CClF
2
, CH
2
Cl, CHF
2
, CF
3
, CH
2
CH
2
Br, CH
2
CF
3
, CH
2
CH
2
F, C
2
Cl
5
, CH
2
Br, CHBrCl, CH
2
CH
2
CF
3
etc.
Alkoxy is typically methoxy, ethoxy, propyloxy, isopropyloxy, n-butyloxy, isobutyloxy, sec-butyloxy and tert-butyloxy. Methoxy and ethoxy are preferred.
Alkylthio is typically methylthio or ethylthio.
Haloalkoxy is any alkoxy substituted with one or more halogen atoms. Typical examples are difluoromethoxy, trifluoromethoxy, 2,2,-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2-difluoroethoxy.
Aryl can be for example phenyl or naphthyl.
Arylalkyl can be for example benzyl, 2-phenyl-ethyl or 3-phenyl-propyl.
Heteroaryl stands for aromatic ring systems comprising mono-, bi- or tricyclic systems wherein at least one oxygen, nitrogen or sulfur atom is present as a ring member. Examples 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, benzotroazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.
Alkanoyl is, in accordance with the number of carbon atoms embraced, either straight-chain or branched. Typical examples are formyl, acetyl, propionyl, butyryl or pivaloyl.
As a result of the presence of at least one asymmetric carbon atom and/or at least one asymmetric sulfur atom in the compounds of formula I the compounds may occur in the form of optical isomers. Owing to the presence of an aliphatic —C═C— double bond, geometrical isomerism may also occur. Formula I is intended to encompass all of those possible isomeric forms and mixtures thereof.
Preference is given to compounds of formula I wherein
n is the number zero or one;
R
1
is C
1
-C
10
alkenyl, C
2
-C
10
alkenyl, C
2
-C
10
alkynyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cycloalkyl-C
1
-C
6
alkyl,
C
6
-C
10
aryl, or C
6
-C
10
aryl-C
1
-C
6
alkyl that are optionally mono- or poly-substituted by C
1
-C
8
alkyl, C
1
-C
8
alkoxy, C
1
-C
8
alkylthio, C
1
-C
8
alkylsulfonyl, C
3
-C
8
cycloalkyl, C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, C
3
-C
8
alkynyloxycarbonyl, C
3
-C
8
cycloalkyl-C
1
-C
6
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
3
-C
8
alkenyloxy, C
3
-C
8
alkynyloxy, C
1
-C
8
alkanoyl (where all these alkyl, alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, cyano or nitro; or a group NR
a
R
b
, wherein R
a
and R
b
are each independently of the other hydrogen, C
1
-C
8
alkyl or together are C
2
-C
7
alkylen;
R
2
is hydrogen or C
1
-C
8
alkyl;
R
3
is phenyl, naphthyl or heteroaryl formed by 1 or 2 five- or six-membered rings containing 1 to 4 identical or different heteroatoms selected from oxygen, nitrogen or sulfur and are optionally mono- or poly-substituted by C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
1
-C
8
alkoxy, C
1
-C
8
alkylthio, C
1
-C
8
alkylsulfonyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cycloalkyl-C
1
-C
6
alkyl, C
1
-C
4
alkylendioxy, C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, C
3
-C
8
alkynyloxycarbonyl, C
3
-C
8
cycloalkyloxy, C
3
-C
8
alkenyloxy, C
3
-C
8
alkynyloxy, C
1
-C
8
alkanoyl, C
1
-C
8
dialkylamino, C
1
-C
8
alkylamino (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated), halogen, nitro, cyano, hydroxy or amino;
A is C
1
-C
8
alkylen; and
B is phenyl optionally mono- or poly-substituted by C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkynyl, C
1
-C
8
alkoxy, C
1
-C
8
alkylthio, C
1
-C
8
alkylsulfonyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cycloalkyl-C
1
-C
6
alkyl, C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, C
3
-C
8
alkynyloxycarbonyl, C
3
-C
8
cycloalkyloxy, C
3
-C
8
alkenyloxy, C
3
-C
8
alkynyloxy, C
1
-C
8
alkanoyl, C
1
-C
8
dialkylamino, C
1
-C
8
alkylamino, C
6
-C
10
aryloxy, C
6
-C
10
aryl-C
1
-C
6
alkoxy, C
6
-C
10
aryl-C
1
-C
6
alkenyloxy, C
6
-C
10
aryl-C
1
-C
6
alkynyloxy, C
1
-C
8
alkanoyloxy (where all these alkyl alkenyl, alkynyl or cycloalkyl containing groups may be partially or fully halogenated and where all aryl containin

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