Halopyrimidines

Details Halopyrimidines Halopyrimidines

2001-12-14

2004-01-27

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S319000

Reexamination Certificate

active

06683029

ABSTRACT:

The invention relates to novel halogenopyrimidines, to a pluarity of processes for their preparation and to their use as pesticides.
Certain pyrimidines having a similar substitution pattern, and their fungicidal action, are already known (GB-A 2253624). However, the activity of these prior-art compounds is, in particular at low application rates and concentrations, not entirely satisfactory in all areas of use.
This invention, accordingly, provides the novel halogenopyrimidines of the general formula (I)
in which
z represents in each case substituted or unsubstituted cycloalkyl, aryl or hetero-cyclyl,
Q represents oxygen or sulphur,
X represents halogen and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another each represents hydrogen, halogen, cyano, nitro, in each case optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with heteroatoms, such as, for example, in alkoxy, alkylthio or alkylamino. Unless stated otherwise, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and also aromatic, cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen and sulphur. If the ring contains a plurality of oxygen atoms, these are not adjacent. If appropriate, the cyclic compounds form, together with other carbocyclic or heterocyclic, fused-on or bridged rings, a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic cyclic compounds which, if appropriate, form a polycyclic ring system with other carbocyclic, fused-on or bridged rings.
A polycyclic ring system can be linked to a heterocyclic ring or a fused-on carbocyclic ring. The thus-described heterocyclyl can also be mono- or polysubstituted, preferably by methyl, ethyl or halogen. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Halogenoalkoxy represents partially or fully halogenated alkoxy. In the case of polyhalogenated halogenoalkoxy, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and, in particular, chlorine. If the halogenoalkoxy carries further substituents, the maximum number of halogen atoms which is possible is reduced to the remaining free valencies. Unless stated otherwise, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
Halogenoalkyl represents partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms can be identical or different. Preferred halogen atoms are fluorine and chlorine, in particular fluorine. If the halogenoalkyl carries other substituents, the maximum possible number of halogen atoms is reduced to the remaining free valencies. Unless stated otherwise, preference is given to hydrocarbon chains having 1 to 6 carbon atoms.
Furthermore, it has been found that the novel halogenopyrimidines of the general formula (I) are obtained when
a) 2-(2-hydroxy-phenyl)-2-methoxyiminoacetates of the formula (II)
 in which
L
1
, L
2
, L
3
and L
4
are each as defined above
are reacted with a substituted halogenopyrimidine of the general formula (III)
 in which
Z, Q and X are each as defined above and
Y
1
represents halogen,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst, or when
b) phenoxypyrimidines of the general formula (IV)
 in which
X, L
1
, L
2
, L
3
and L
4
are each as defined above and
Y
2
represents halogen
are reacted with a cyclic compound of the general formula (V)
Z—Q—H  (V)
in which
Z and Q are each as defined above,
if appropriate in the presence of a diluent, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a catalyst.
Finally, it has been found that the novel halogenopyrimidines of the general formula (I) have very strong activity against pests of plants.
If appropriate, the compounds according to the invention can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z. What is claimed are both the E and the Z isomers, and any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which
Z represents cycloalkyl having 3 to 7 carbon atoms which is in each case optionally mono- or disubstituted by halogen, alkyl or hydroxyl;
represents heterocyclyl having 3 to 7 ring members which is optionally substituted by alkyl having 1 to 4 carbon atoms or halogen;
or represents phenyl or naphthyl, each of which is optionally mono- to tetrasubstituted by identical or different substituents, where the possible substituents are preferably selected from the list below:
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, thio-carbamoyl;
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, mercaptoalkyl, alkyl-sulphinyl or alkylsulphonyl having in each case 1 to 8 carbon atoms;
in each case straight-chain or branched alkenyl or alkenyloxy having in each case 2 to 6 carbon atoms;
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms;
in each case straight-chain or branched halogenoalkenyl or halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms;
in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, arylalkylaminocarbonyl, dialkylaminocarbonyloxy, alkenylcarbonyl or alkinylcarbonyl, having 1 to 6 carbon atoms in the respective hydrocarbon chains;
cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms; in each case doubly attached alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms or dioxyalkylene having 1 or 2 carbon atoms, each of which is optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of fluorine, chlorine, oxo, methyl, trifluoromethyl and ethyl;
or a grouping
 in which
A
1
represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon atoms or cycloalkyl having 1 to 6 carbon atoms and
A
2
represents hydroxyl, amino, methylamino, phenyl, benzyl or represents in each case optionally cyano-, hydroxyl-, alkoxy-, alkylthio-, alkylamino-, dialkylamino- or phenyl-substituted alkyl or alkoxy having 1 to 4 carbon atoms, or represents alkenyloxy or alkinyloxy having in each case 2 to 4 carbon atoms,
and phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, heterocyclyl or phenylalkyl, phenylalkyloxy, phenylalkylthio or heterocyclylalkyl having in each case 1 to 3 carbon atoms in the respective alkyl moieties and being in each case optionally mono- to trisubstituted in the ring moiety by halogen and/or straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms,
Q represents oxygen or sulphur,
X represents fluorine, chlorine or bromine and
L
1
, L
2
, L
3
and L
4
are identical or different and independently of one another e

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