Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-03-09
2001-08-21
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C544S278000
Reexamination Certificate
active
06277858
ABSTRACT:
The present invention relates to novel pyrimidin-4-one and pyrimidin-4-thione derivatives of formula I, which have pesticidal activity, in particular fungicidal activity,
wherein
A is phenyl, thienyl (including all 3 isomers), thiazolyl, pyridyl or pyridazinyl;
X is oxygen or sulfur;
R
1
is hydrogen, halogen or trimethylsilyl;
R
2
is hydrogen, halogen or trimethylsilyl; at least one of R
1
and R
2
is not hydrogen;
R
3
is C
1
-C
8
alkyl, C
1
-C
8
alkenyl, C
1
-C
8
alkinyl which are unsubstituted or mono to tri-substituted by C
3
-C
6
cycloalkyl, halogen, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; O—C
1
-C
6
alkyl, O—C
2
-C
6
alkenyl, O—C
2
-C
6
alkynyl, which are unsubstituted or mono to tri-substituted by C
3
-C
6
cycloalkyl, halogen or C
1
-C
6
alkoxy; N—C
1
-C
6
alkyl; or N═CHC
1
-C
6
alkyl;
R
4
is C
1
-C
8
alkyl, C
1
-C
8
alkenyl, C
1
-C
8
alkinyl which are unsubstituted or mono to tri-substituted by C
3
-C
6
cycloalkyl, halogen, cyano, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; C
1
-C
4
alkoxy-C
1
-C
4
alkoxy; C
1
-C
4
alkoxy-C
1
-C
4
alkylthio; nitro; —CO—C
1
-C
6
alkyl; C
3
-C
6
cycloalkyl; or phenyl, which is unsubstituted or mono to tri-substituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, cyano, nitro, amino, mono-C
1
-C
6
alkylamino, di-C
1
-C
6
alkyl-amino, C
1
-C
6
alkylthio, phenyl or phenoxy and in which the phenyl part is unsubstituted or mono to tri-substituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy.
The invention also relates to the preparation of these compounds, to agrochemical compositions comprising as active ingredient at least one of these compounds, as well as to the use of the active ingredients or compositions for pest control, in particular as fungicides, in agriculture and horticulture.
The compounds I and, optionally, their tautomers may be obtained in the form of their salts. Because the compounds I have at least one basic center they can, for example, form acid addition salts. Said acid addition salts are, for example, formed with mineral acids, typically sulfuric acid, a phosphoric acid or a hydrogen halide, with organic carboxylic acids, typically acetic acid, oxalic acid, malonic acid, maleic acid, fumaric acid or phthalic acid, with hydroxycarboxylic acids, typically ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or with benzoic acid, or with organic sulfonic acids, typically methanesulfonic acid or p-toluenesulfonic acid.
Together with at least one acidic group, the compounds of formula I can also form salts with bases. Suitable salts with bases are, for example, metal salts, typically alkali metal salts or alkaline earth metal salts, e.g. sodium salts, potassium salts or magnesium salts, or salts with ammonia or an organic amine, e.g. morpholine, piperidine, pyrrolidine, a mono-, di- or trialkylamine, typically ethylamine, diethylamine, triethylamine or dimethylpropylamine, or a mono-, di- or trihydroxyalkylamine, typically mono-, di- or triethanolamine. Where appropriate, the formation of corresponding internal salts is also possible. Within the scope of this invention, agrochemical acceptable salts are preferred.
Where asymmetrical carbon atoms are present in the compounds of formula I, these compounds are in optically active form. Owing to the presence of double bonds, the compounds can be obtained in the [E] and/or [Z] form. Atropisomerism can also occur. The invention relates to the pure isomers, such as enantiomers and diastereomers, as well as to all possible mixtures of isomers, e.g. mixtures of diastereomers, racemates or mixtures of racemates.
The general terms used hereinabove and hereinbelow have the following meanings, unless otherwise defined:
Alkyl groups on their own or as structural element of other groups such as alkoxy are, in accordance with the number of carbon atoms, straight-chain or branched and will typically be methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl, 1-hexyl, 3-hexyl, 1-heptyl or 1-octyl.
Alkenyl will be understood as meaning straight-chain or branched alkenyl such as allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, 1-pentenyl, 1-hexenyl, 1-heptenyl or 1-octenyl. 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-1-yn-1-yl, but-1-yn-3-yl, 1-pentinyl, 1-hexinyl, 1-heptinyl or 1-octinyl. The preferred meaning is propargyl.
Halogen and halo substituents will be understood generally as meaning fluorine, chlorine, bromine or iodine. Fluorine, chlorine or bromine are preferred meanings.
Haloalkyl can contain identical or different halogen atoms, typically fluoromethyl, difluoromethyl, difluorochloromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2,2,2-trichloroethyl, 3,3,3-trifluoropropyl.
Cycloalkyl is, depending on the ring size, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cycooctyl.
Preferred compounds are those of formula I, wherein
A is thienyl, including all 3 isomers (subgroup A).
Within the scope of said subgroup A, those compounds of formula I are preferred wherein
R
1
is hydrogen, fluorine, chlorine, bromine or iodine;
R
2
is hydrogen, fluorine, chlorine, bromine or iodine; at least one of R
1
and R
2
is not hydrogen;
R
3
is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkinyl which are unsubstituted or mono to tri-substitute by C
3
-C
6
cycloalkyl, halogen or C
1
-C
4
alkoxy; O—C
1
-C
6
alkyl, O—C
2
-C
6
alkenyl, O—C
2
-C
6
alkynyl, which are unsubstituted or mono to tri-substituted by C
3
-C
6
cycloalkyl, halogen or C
1
-C
4
alkoxy; N—C
1
-C
6
alkyl; or N═CHC
1
-C
6
alkyl;
R
4
is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkinyl which are unsubstituted or mono to tri-substituted by C
3
-C
6
cycloalkyl, halogen or C
1
-C
4
alkyoxy; or phenyl which is unsubstituted or mono to tri-substituted by fluorine, chlorine, bromine, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, phenyl or phenoxy and in which the phenyl part is unsubstituted or mono to tri-substituted by fluorine, chlorine, bromine, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy (subgroup B).
A special group within the scope of subgroup B is that of the compounds of formula I, wherein
R
3
is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkinyl which are unsubstituted or mono to tri-substituted by C
3
-C
4
cycloalkyl, fluorine, chlorine, bromine or C
1
-C
4
alkoxy; O—C
1
-C
6
alkyl; O—C
2
-C
6
alkenyl;
O—C
2
-C
6
alkynyl; N—C
1
-C
6
alkyl; or N═CHC
1
-C
6
alkyl;
R
4
is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkinyl which are unsubstituted or mono to tri-substituted by C
3
-C
4
cycloalkyl, fluorine, chlorine, bromine or C
1
-C
4
alkoxy; or phenyl which is unsubstituted or mono to tri-substituted by fluorine, chlorine, bromine, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, phenyl or phenoxy and in which the phenyl part is unsubstituted or mono to tri-substituted by fluorine, chlorine or bromine (subgroup C).
A preferred group within the scope of subgroup C is that of the compounds of the formula I, wherein
A is thienyl[2.3-d],
X is oxygen,
R
1
is hydrogen, chlorine or bromine;
R
2
is hydrogen, chlorine or bromine; at least one of R
1
and R
2
is not hydrogen;
R
3
is C
3
-C
5
alkyl or O—C
1
-C
4
alkyl;
R
4
is C
2
-C
5
alkyl or phenyl which is unsubstituted or mono to tri-substituted by fluorine, chlorine, bromine, C
1
-C
4
alkyl or phenoxy and in which the phenoxy is unsubstituted or mono to tri-substituted by fluorine, chlorine or bromine (subgroup D1).
Another preferred group within the scope of subgroup C is that of compounds of the formula I, wherein
A is thienyl[2.3-d],
X is sulfur,
R
1
is hydrogen, chlorine or bromine;
R
2
is hydrogen, chlorine or bromine; at least one of R
1
and R
2
is n
Liu Hong
Shah Mukund J.
Syngenta Crop Protection Inc.
Teoli, Jr. William A.
LandOfFree
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