Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives

Details Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives Pyrimidin-2-oxy-4-one and pyrimidin-2-oxy-4-thione derivatives

2000-03-03

2002-08-27

Shah, Mukuid J. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C549S052000, C549S050000, C544S229000, C544S278000, C544S298000, C544S315000

Reexamination Certificate

active

06441169

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 or pyridyl;
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
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
haloalkynyl, —(CH
2
)
n
—C
3
-C
8
cycloalkyl which are unsubstituted or mono- to tri-substituted by halogen, C
1
-C
6
alkyl or C
1
-C
6
haloalkyl; C
1
-C
4
alkoxy-C
1
-C
6
alkyl; C
1
-C
4
alkoxy-C
2
-C
6
alkenyl; C
1
-C
4
alkoxy-C
2
-C
6
alkynyl; C
1
-C
1
-C
4
alkylthio-C
1
-C
6
alkyl; C
1
-C
4
alkylthio-C
2
-C
6
alkenyl; C
1
-C
4
alkylthio-C
2
-C
6
alkynyl; mono-C
1
-C
4
alkylamin-C
1
-C
6
alkyl; mono-C
1
-C
4
alkylamin-C
2
-C
6
alkenyl; mono-C
1
-C
4
alkylamin-C
2
-C
6
alkynyl; —(CH
2
)
n
—C
1
-C
4
alkoxy-C
3
-C
6
cycloalkyl; —(CH
2
)
n
—C
1
-C
4
alkylthio-C
3
-C
6
cycloalkyl; —(CH
2
)
n
-mono-C
1
-C
4
alkylamin-C
3
-C
6
cycloalkyl; or N═CR
9
R
10
;
n is 1, 2, 3 or 4;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or halogen, wherein at least one of the substituents R
4
-R
8
must be from hydrogen; and
R
9
is hydrogen, C
1
-C
6
alkyl, C
3
-C
7
cycloalkyl, pyridyl, furyl, thienyl or phenyl which is unsubstituted or mono to pentasubstituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy;
R
10
is hydrogen, C
1
-C
6
alkyl, C
3
-C
7
cycloalkyl, pyridyl, furyl, thienyl or phenyl which is unsubstituted or mono to pentasubstituted by halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; and at least one of R
9
and R
10
is not hydrogen.
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 or 3-hexyl.
Alkenyl will be understood as meaning straight-chain or branched alkenyl such as allyl, methallyl, 1-methylvinyl or but-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-1-yn-1-yl or but-1-yn-3-yl. 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 cyclooctyl.
Preferred compounds are those of formula I, wherein
A is thienyl, including all 3 isomers and
X is oxygen (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
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
haloalkynyl or CH
2
—C
3
-C
4
cycloalkyl which are unsubstituted or substituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, fluorine, chlorine, bromine, iodine, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, wherein at least one of the substituents R
4
-R
8
must be different from hydrogen (subgroup B).
Within the scope of subgroup B those compounds of formula I are particularly preferred, wherein
R
3
is C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, each of which is unsubstituted or substituted by chlorine or bromine; or CH
2
—C
3
-C
6
cycloalkyl, which is unsubstituted or substituted by fluorine, chlorine, bromine or iodine;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, fluorine, chlorine, bromine, iodine, C
1
-C
4
alkyl or C
1
-C
2
haloalkyl, wherein at least one of the substituents R
4
-R
8
must be different from hydrogen (subgroup C).
A special group within the scope of subgroup C is that of the compounds of formula I, wherein
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
1
-C
4
alkyl or CH
2
-cyclopropyl;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, chlorine, bromine, iodine, C
1
-C
4
alkyl or C
1
-C
2
haloalkyl, wherein at least one of the substituents R
4
-R
8
must be different from hydrogen (subgroup D).
A preferred group within the scope of subgroup D is that of the compounds of the formula I, wherein
A is thienyl[2.3-d],
R
3
is C
3
-C
4
alkyl,
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, chlorine, bromine, methyl or CF
3
, wherein at least one of the substituents R
4
-R
8
must be different from hydrogen (subgroup E).
Another preferred group within the scope of subgroup D is that of the compounds of the formula I, wherein
A is thienyl[3.2-d];
R
3
is C
3
-C
4
alkyl;
R
4
, R
5
, R
6
, R
7
and R
8
are each independently of the other hydrogen, chlorine, bromine, methyl or CF
3
, wherein at least one of the substituents R
4
-R
8
must be different from hydrogen (subgroup F).
An

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