Pyrimidin-4-enamine as fungicide

Details Pyrimidin-4-enamine as fungicide Pyrimidin-4-enamine as fungicide

2001-05-04

2003-09-09

Raymond, Richard L. (Department: 1624)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C514S264100, C514S265100, C514S266400, C544S255000, C544S256000, C544S257000, C544S278000, C544S279000, C544S280000, C544S283000, C564S247000, C504S222000, C504S240000, C504S241000

Reexamination Certificate

active

06617330

ABSTRACT:

The present invention relates to novel pyrimidine derivatives of formula I, which have pesticidal activity, in particular fungicidal and insecticidal activity,
wherein
A is a 5- or 6-membered ring which may be saturated or unsaturated, aromatic or non-aromatic and which may contain no hetero atoms or 1-3 hetero atoms O, S and/or N, each in the free form or in salt form; with the exception of the imidazolyl ring;
R
1
, R
2
and R
3
are each independently of the other hydrogen; halogen; C
1
-C
8
alkyl, C
2
-C
8
alkenyl or C
2
-C
8
alkinyl which are unsubstituted or mono- to tri-substituted by C
3
-C
6
cycloalkyl, halogen, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkoxy; O—C
1
-C
6
alkyl, O—C
2
-C
6
alkenyl, O—C
2
-C
6
alkynyl, S—C
1
-C
6
alkyl, S—C
2
-C
6
alkenyl or S—C
2
-C
6
alkynyl, 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; cyano; nitro; or trimethylsilyl; provided that R
1
, R
2
and R
3
are not hydrogen at the same time;
R
4
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl or C
2
-C
8
alkinyl which are unsubstituted or mono- to tri-substituted by C
3
-C
6
cycloalkyl, halogen, cyano, nitro, CO—C
1
-C
4
alkyl, COO—C
1
-C
4
alkyl, CO-aryl, COO-aryl, C
1
-C
6
alkylthio, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; C
3
-C
6
cycloalkyl which is unsubstituted or mono- to tri-substituted by C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, halogen, cyano, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkinyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy or C
1
-C
6
haloalkyl; NHR
7
; SR
7
or OR
7
;
R
5
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl or C
2
-C
8
alkinyl which are unsubstituted or mono- to tri-substituted by C
3
-C
6
cycloalkyl, halogen, cyano, nitro, CO—C
1
-C
4
alkyl, COO—C
1
-C
4
alkyl, CO-aryl, COO-aryl, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkoxy; C
3
-C
6
cycloalkyl which is unsubstituted or mono- to tri-substituted by C
1
-C
6
alkyl, halogen, cyano, C
1
-C
6
alkoxy, C
1
-C
6
haloalkyl or C
1
-C
6
haloalkoxy;
R
6
is hydrogen; C
1
-C
8
alkyl, C
2
-C
8
alkenyl or C
2
-C
8
alkinyl which are unsubstituted or mono- to tri-substituted by C
3
-C
6
cycloalkyl, halogen, cyano, nitro, CO—C
1
-C
4
alkyl, COO—C
1
-C
4
alkyl, CO-aryl, COO-aryl, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkoxy; C
3
-C
6
cycloalkyl which is unsubstituted or mono- to tri-substituted by C
1
-C
6
alkyl, halogen, cyano, C
1
-C
6
alkoxy, C
1
-C
6
haloalkyl or C
1
-C
6
haloalkoxy; O—C
1
-C
6
alkyl, O—C
2
-C
6
alkenyl, O—C
2
-C
6
alkynyl, S—C
1
-C
6
alkyl, S—C
2
-C
6
alkenyl or S—C
2
-C
6
alkynyl, 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; aryl or heteroaryl which are unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; CO—C
1
-C
6
alkyl; CO—C
1
-C
6
alkyl-O—C
1
-C
6
alkyl; CO—C
1
-C
6
haloalkyl; CO-heteroaryl; SO
2
—C
1
-C
6
alkyl; SO
2
-aryl; CO-phenyl or CO—C
1
-C
6
alkyl-O-phenyl in which phenyl is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; COOR
8
wherein R
8
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkinyl, C
3
-C
4
cycloalkyl or phenyl which is unsubstituted or mono- to tri-substituted by halogen, cyano, nitro, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; cyano; nitro; or halogen; and
R
7
is C
1
-C
8
alkyl, C
2
-C
8
alkenyl or C
2
-C
8
alkinyl which are unsubstituted or mono- to tri-substituted by C
3
-C
6
cycloalkyl, halogen, cyano, nitro, CO—C
1
-C
4
alkyl, COO—C
1
-C
4
alkyl, CO-aryl, COO-aryl, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or C
1
-C
6
haloalkoxy; C
3
-C
6
cycloalkyl which is unsubstituted or mono- to tri-substituted by C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, halogen, cyano, C
1
-C
6
alkoxy or C
1
-C
6
haloalkoxy; phenyl or benzyl, in which the phenyl group is unsubstituted or mono- to pentasubstituted by halogen, cyano, nitro, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkinyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy or C
1
-C
6
haloalkyl.
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 or insecticides, in agriculture and horticulture.
The compounds I and, optionally, all their isomers 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, cyclohenyl, cycloheptyl or cycooctyl.
Aryl is phenyl, benzyl or naphthyl. Phenyl is preferred. Heteroaryl is pyridinyl, pyrimidinyl, triazinyl, triazolyl, thienyl, thiazoly

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