Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-07-11
2002-10-22
Rotman, Alan L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S247000, C564S079000, C564S080000, C564S097000, C564S381000
Reexamination Certificate
active
06469005
ABSTRACT:
The present invention relates to novel propargylether 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 propargylether derivatives of the general formula I
including the optical isomers thereof and mixtures of such isomers, wherein
R
1
is hydrogen, alkyl, cycloalkyl or optionally substituted aryl,
R
2
and R
3
are each independently hydrogen or alkyl,
R
4
is alkyl, alkenyl or alkynyl,
R
5
, R
6
, R
7
, and R
8
are each independently hydrogen or alkyl and
R
10
is optionally substituted aryl or optionally substituted heteroaryl,
R
11
is hydrogen or optionally substituted alkyl, alkenyl or alkynyl,
Z is hydrogen —CO—R
16
, —COOR
16
, —CO—COOR
16
or —CONR
16
R
17
,
R
12
is hydrogen, or optionally substituted alkyl, alkenyl or alkynyl,
R
13
is hydrogen or alkyl,
R
14
is hydrogen, alkyl, cycloalkyl or cycloalkyl-alkyl,
R
15
is alkyl, alkenyl, alkynyl, optionally substituted aryl or optionally substituted aryl-alkyl, and
R
16
and R
17
are independently of each other hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heteroaryl.
In the above definition aryl includes aromatic hydrocarbon rings like phenyl, naphthyl, anthracenyl, phenanthrenyl and biphenyl like 1,3-biphenyl and 1,4-biphenyl, with phenyl being preferred.
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, benzotriazolyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, phthalazinyl, quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl.
The above aryl and heteroaryl groups may be optionally substituted. This means they may carry one or more identical or different substituents. Normally not more than three substituents are present at the same time. Examples of substituents of aryl or heteroaryl groups are: alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenyl-alkyl, 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; or alkynyloxycarbonyl.
Optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl groups may carry one or more substituents selected from halogen, alkyl, alkoxy, alkylthio, nitro, cyano, hydroxy, mercapto, alkylcarbonyl or alkoxycarbonyl. Preferably, the number of substituents is no more than three with the exception of halogen, where the alkyl groups may be perhalogenated.
In the above definitions “halogen” includes fluorine, chlorine, bromine and iodine.
The alkyl, alkenyl and alkynyl radicals may be straight-chain or branched. This applies also to the alkyl, alkenyl or alkynyl parts 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, 1-propenyl, 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-2butynyl or octyn-1-yl.
A haloalkyl group may contain one or more (identical or different) halogen atoms, and for example may stand for 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 in the compounds of formula I means that the compounds may occur in optically isomeric and enantiomeric 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.
Preferred subgroups of compounds of formula I are those wherein
R
1
is hydrogen, alkyl, cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by substituents selected from the group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may in turn be substituted by one or several halogens; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl; or alkynyloxycarbonyl; or
R
1
is hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-cycloalkyl, phenyl or naphthyl; phenyl and naphthyl being optionally substituted by one to three substituents selected from the group comprising C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
1
-C
8
-haloalkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-haloalkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-haloalkylthio, C
1
-C
8
-alkylsulfonyl, halogen, cyano, nitro and C
1
-C
8
-alkoxycarbonyl; or
R
1
is hydrogen, C
1
-C
8
-alkyl, phenyl optionally substituted by one to three substituents selected from the group comprising C
1
-C
8
-alkyl, C
1
-C
8
-haloalkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-haloalkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-haloalkylthio, halogen, cyano, nitro and C
1
-C
8
-alkoxycarbonyl; or
R
2
and R
3
are hydrogen; or
R
4
is alkyl; or
R
5
, R
6
, and R
7
are hydrogen; or
R
8
is C
1
-C
6
-alkyl; or
R
4
is C
1
-C
6
-alkyl; or
R
8
is methyl or ethyl; or
R
4
is methyl or ethyl; or
R
10
is aryl or heteroaryl, each optionally substituted by substituents selected from to group comprising alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl-alkyl, phenyl and phenylalkyl, where all these groups may be substituted by one or several halogens; alkoxy, alkenyloxy, alkynyloxy; alkoxy-alkyl; haloalkoxy; alkylthio; haloalkylthio; alkylsulfonyl; formyl; alkanoyl; hydroxy; halogen; cyano; nitro; amino; alkylamino; dialkylamino; carboxy; alkoxycarbonyl; alkenyloxycarbonyl and alkynyloxycarbonyl; or
R
10
is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, C
2
-C
8
-alkynyl, C
1
-C
8
-haloalkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-haloalkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-haloalkylthio, C
1
-C
8
-alkylsulfonyl, halogen, cyano, nitro and C
1
-C
8
-alkoxycarbonyl; or
R
10
is phenyl, naphthyl, 1,3-biphenyl or 1,4-biphenyl, each optionally substituted by one to three substituents selected from the group comprising C
1
-C
8
-alkyl, C
1
-C
8
-haloalkyl, C
1
-C
8
-alkoxy, C
1
-C
8
-haloalkoxy, C
1
-C
8
-alkylthio, C
1
-C
8
-haloalkylthio, halogen, cyano, nitro and C
1
-C
8
-alkoxycarbonyl; or
R
11
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
3
-C
4
-alkenyl or C
3
-C
4
-alkynyl
Jeanguenat André
Kunz Walter
Lamberth Clemens
Zeller Martin
Hamilton Thomas
Reyes Hector M
Rotman Alan L.
Syngenta Participations (AG)
Teoli, Jr. William A.
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