Halogen pyrimidines and its use thereof as parasite abatement means

Compounds of the formula (I) ##STR1## in which A represents optionally substituted alkanediyl, PA1 R represents in each case optionally substituted cycloalkyl, aryl or benzo-fused heterocyclyl, PA1 E represents --CH.dbd. or nitrogen, PA1 Q represents oxygen, sulphur, --CH.sub.2 --O--, a single bond, or a nitrogen atom which is optionally substituted by alkyl, and PA1 X represents halogen.

This invention relates to new halogenopyrimidines, to a process for their 
preparation, and to their use as pesticides. 
Certain pyrimidines which have a similar substitution pattern have already 
been disclosed (WO-A 9504728). 
However, the activity of these prior-art compounds is not entirely 
satisfactory in all fields of application, in particular when low rates 
and concentrations are applied. 
There have now been found the new halogenopyrimidines of the general 
formula (I) 
##STR2## 
in which A represents optionally substituted alkanediyl, 
R represents in each case optionally substituted cycloalkyl, aryl or 
benzo-fused heterocyclyl, 
E represents --CH.dbd. or nitrogen, 
Q represents oxygen, sulphur, --CH.sub.2 --O--, a single bond, or a 
nitrogen atom which is optionally substituted by alkyl, and 
X represents halogen. 
Furthermore, it has been found that the new halogenopyrimidines of the 
general formula (I) are obtained when 
a) hydroxy compounds of the general formula (II) 
##STR3## 
in which A and E have the abovementioned meanings, 
are reacted with a substituted halogenopyrimidine of the general formula 
(III) 
##STR4## 
in which R, Q and X have the abovementioned meanings and 
Y.sup.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) 
##STR5## 
in which A, E and X have the abovementioned meanings and 
Y.sup.2 represents halogen 
are reacted with a cyclic compound of the general formula (V) 
EQU R--Q--H (V) 
in which 
R and Q have the abovementioned meanings, 
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 new halogenopyrimidines of the general 
formula (I) have a very powerful fungicidal activity. 
Where appropriate, the compounds according to the invention can exist in 
the form of mixtures of various isomeric forms which are possible, in 
particular of stereoisomers, such as, for example, E and Z isomers. 
Claimed are not only the E and the Z isomers, but also any mixtures of 
these isomers. 
The invention preferably relates to compounds of the formula (I) in which 
A represents alkanediyl having 1 to 5 carbon atoms which is optionally 
substituted by halogen, 
R represents cycloalkyl having 3 to 7 carbon atoms which is in each case 
optionally monosubstituted to disubstituted by halogen, alkyl or hydroxyl; 
or represents benzodioxanyl which is optionally substituted by alkyl having 
1 to 4 carbon atoms; 
or represents phenyl or naphthyl, each of which is optionally 
monosubstituted to tetrasubstituted by identical or different 
substituents, other substituents which are possible preferably being 
selected from amongst the enumeration which follows: 
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, 
thiocarbamoyl; 
in each case straight-chain or branched alkyl, hydroxyalkyl, oxoalkyl, 
alkoxy, alkoxyalkyl, alkylthioalkyl, dialkoxyalkyl, alkylthio, 
alkylsulphinyl or alkylsulphonyl, each of which has 1 to 8 carbon atoms; 
in each case straight-chain or branched alkenyl or alkenyloxy, each of 
which as 2 to 6 carbon atoms; 
in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, 
halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl, each 
of which has 1 to 6 carbon atoms and 1 to 13 identical or different 
halogen atoms; 
in each case straight-chain or branched halogenoalkenyl or 
halogenoalkenyloxy, each of which has 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, 
alenylcarbonyl or alkinylcarbonyl, each of which has 1 to 6 carbon atoms 
in the respective hydrocarbon chains; 
cycloalkyl or cycloalkyloxy, each of which has 3 to 6 carbon atoms; 
alkylene having 3 or 4 carbon atoms, oxyalkylene having 2 or 3 carbon atoms 
or dioxyalkylene having 1 to 2 carbon atoms, in each case optionally 
monosubstituted to tetrasubstituted by identical or different substituents 
from the series consisting of fluorine, chlorine, oxo, methyl, 
trifluoromethyl or ethyl; 
or a group 
##STR6## 
where A.sup.1 represents hydrogen, hydroxyl or alkyl having 1 to 4 carbon 
atoms or cycloalkyl having 1 to 6 carbon atoms and 
A.sup.2 represents hydroxyl, amino, methylamino, phenyl, benzyl, or 
represents alkyl or alkoxy having 1 to 4 carbon atoms, each of which is 
optionally substituted by cyano, hydroxy, alkoxy, alkylthio, alkylamino, 
dialkylamino or phenyl, or represents alkenyloxy or alkinyloxy, each of 
which has 2 to 4 carbon atoms, 
and also phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, 
heterocyclyl, phenylalkyl, phenylalkyloxy, phenylalkylthio or 
heterocyclylalkyl, each of which has 1 to 3 carbon atoms in the respective 
alkyl moieties and each of which is optionally monosubstituted to 
trisubstituted in the cyclic moiety by halogen and/or straight-chain or 
branched alkyl or alkoxy having 1 to 4 carbon atoms, 
E represents --CH.dbd. or nitrogen, 
Q represents oxygen, sulphur, a single bond or a nitrogen atom which is 
optionally substituted by methyl, ethyl or n- or i-propyl and 
X represents fluorine, chlorine, bromine or iodine. 
In the definitions, the saturated or unsaturated hydrocarbon chains, such 
as alkyl, alkanediyl, alkenyl or alkinyl, also together with hetero atoms, 
such as, for example, in alkoxy, alkylthio or alkylamino, are in each case 
straight-chain or branched. 
In particular, the invention relates to compounds of the formula (I) in 
which 
A represents methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, 
propane-1,2-diyl, propane-1,3-diyl, butane-1,1-diyl, butane-1,2-diyl, 
butane-1,3-diyl or butane-2,2-diyl, each of which is optionally 
substituted by fluorine or chlorine, 
represents cyclopentyl or cyclohexyl, each of which is optionally 
monosubstituted to disubstituted by fluorine, chlorine, methyl, ethyl or 
hydroxyl; 
or represents benzodioxanyl which is optionally substituted by methyl or 
ethyl; 
or represents phenyl or naphthyl, each of which is optionally 
monosubstituted to tetrasubstituted by identical or different 
substituents, the substituents which are possible preferably being 
selected from amongst the enumeration which follows: 
fluorine, chlorine, bromine, iodine, cyano, nitro, amino, hydroxyl, formyl, 
carboxyl, carbamoyl, thiocarbamoyl, 
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, 1-, 2-, 3-, 
neo-pentyl, 1-, 2-, 3-, 4-(2-methylbutyl), 1-, 2-, 3-hexyl, 1-, 2-, 3-, 
4-, 5-(2-methylpentyl), 1-, 2-, 3-(3-methylpentyl), 2-ethylbutyl, 1-, 3-, 
4-(2,2-dimethylbutyl), 1-, 2-(2,3-dimethylbutyl), hydroxymethyl, 
hydroxyethyl, 3-oxobutyl, methoxymethyl, dimethoxymethyl, 
methoxy, ethoxy, n- or i-propoxy, 
methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, 
methylsulphonyl or ethylsulphonyl, 
vinyl, allyl, 2-methylallyl, propen-1-yl, crotonyl, propargyl, vinyloxy, 
allyloxy, 2-methylallyloxy, propen-1-yloxy, crotonyloxy, propargyloxy; 
Trifluoromethyl, trifluoroethyl, 
difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, 
difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, 
trifluoromethylsulphinyl or trifluoromethylsulphonyl, 
methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, 
acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylaminocarbonyl, 
ethylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, 
dimethylaminocarbonyloxy, diethylaminocarbonyloxy, benzylaminocarbonyl, 
acryloyl, acryloyl, propioloyl, 
cyclopentyl, cyclohexyl, 
in each case divalent propanediyl, ethyleneoxy, methylenedioxy, 
ethylenedioxy, each of which is optionally monosubstituted to 
tetrasubstituted by identical or different substituents from the series 
consisting of fluorine, chlorine, oxo, methyl or trifluoromethyl, 
or a group 
##STR7## 
where A.sup.1 represents hydrogen, methyl or hydroxyl and 
A.sup.2 represents hydroxyl, methoxy, ethoxy, amino, methylamino, phenyl, 
benzyl or hydroxyethyl, and 
phenyl, phenoxy, phenylthio, benzoyl, benzoylethenyl, cinnamoyl, benzyl, 
phenylethyl, phenylpropyl, benzyloxy, benzylthio, 
5,6-dihydro-1,4,2-dioxazin-3-ylmethyl, triazolylmethyl, 
benzoxazol-2-ylmethyl, 1,3-dioxan-2yl, benzimidazol-2-yl, dioxol-2-yl, 
oxadiazolyl, each of which is optionally monosubstituted to trisubstituted 
in the cyclic moiety by halogen and/or straight-chain or branched alkyl or 
alkoxy having 1 to 4 carbon atoms, 
E represents --CH.dbd. or nitrogen, 
Q represents oxygen, sulphur, a single bond or a nitrogen atom which is 
optionally substituted by methyl, and 
X represents fluorine or chlorine. 
The definitions of radicals given above in general or in preferred ranges 
apply both to the end products of the formula (I) and, analogously, to the 
starting materials or intermediates required in each case for the 
preparation. 
Independently of the combination given in each case, the definitions of 
radicals given individually for these radicals in the respective 
combinations or preferred combinations of radicals are also replaced by 
definitions of radicals of other preferred ranges as required. 
Formula (II) provides a general definition of the hydroxy compounds 
required as starting materials for carrying out Process a) according to 
the invention. In this formula (II), A and E preferably, or in particular, 
have thsoe meanings which have already been given in connection with the 
description of the compounds of the formula (I) according to the invention 
as being preferred, or particularly preferred, for A and E. 
Some of the starting materials of the formula (II) are known, and/or they 
can be prepared by processes known per se (cf. WO-A 9504728). New, and 
also the subject of the present application, are methoxyvinyl compounds of 
the general formula (IIa) 
##STR8## 
in which A has the abovementioned meaning. 
The methoxyvinyl compounds of the formula (IIa) are obtained when (Process 
a-1) tetrahydropyranylethers of the general formula (VI) 
##STR9## 
in which A has the abovementioned meaning, 
are treated 
with an acid, preferably an inorganic or organic protonic or Lewis acid, 
such as, for example, hydrogen chloride, sulphuric acid, phosphoric acid, 
formic acid, acetic acid, trifluoroacetic acid, methanesulphonic acid, 
trifluoromethanesulphonic acid, toluenesulphonic acid, boron trifluoride 
(also as the etherate), boron tribromide, aluminum trichloride, zinc 
chloride, iron(III) chloride, antimony pentachloride, or else with a 
polymeric acid such as, for example, an acidic ion exchanger, an acidic 
aluminum oxide or acidic silica gel, 
at temperatures from -20.degree. C. to 120.degree. C., preferably at 
temperatures from -10.degree. C. to 80.degree. C., 
if appropriate in the presence of a diluent, preferably an ether, such as 
diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl 
ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1.2-diethoxyethane 
or anisole; a sulphoxide, such as dimethyl sulphoxide; a sulphone, such as 
sulpholane; an alcohol such as methanol, ethanol, n- or i-propanol, n-, 
i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, 
methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol 
monoethyl ether, their mixtures with water, or pure water. 
Formula (VI) provides a general definition of the tetrahydropyranyl ethers 
required as starting materials for carrying out Process a-1) according to 
the invention. In this formula (VI), A preferably, or in particular, has 
the meaning which has already been given in connection with the 
description of the compounds of the formula (I) according to the invention 
as being preferred, or particularly preferred, for A. 
The starting materials of the formula (VI) are new and also a subject of 
the present application. 
The tetrahydropyranol ethers of the formula (VI) are obtained when (Process 
a-2) keto compounds of the general formula (VII) 
##STR10## 
in which A has the abovementioned meaning, 
are reacted with methoxymethyl-triphenyl-phosphonium chloride, bromide or 
iodide, if appropriate in the presence of a diluent, preferably an inert 
aprotic solvent such as, for example, an ether such as diethyl ether, 
diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, 
tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; an 
amide such as N,N-dimethylformamide, N,N-dimethylacetamide, 
N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; 
a sulphoxide such as dimethyl sulphoxide, or of a sulphone such as 
sulpholane, and 
if appropriate in the presence of a base, preferably of an alkaline earth 
metal hydride, hydroxide, amide or alcoholate or of an alkali metal 
hydride, hydroxide, amide or alcoholate such as, for example, sodium 
hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium 
tert-butoxide, sodium hydroxide or potassium hydroxide, 
at temperatures from 0.degree. C. to 100.degree. C., preferably from 
20.degree. C. to 80.degree. C. 
Formula (VII) provides a general definition of the keto compounds required 
as starting materials for carrying out Process a-2) according to the 
invention. In this formula (VII), A preferably, or in particular, has the 
meaning which has already been given in connection with the description of 
the compounds of the formula (I) according to the invention as being 
preferred, or particularly preferred, for A. 
The starting materials of the formula (VII) are new and also a subject of 
the present application. 
The keto compounds of the formula (VII) are obtained when (Process a-3) 
halogenophenyl compounds of the general formula (VIII) 
##STR11## 
in which Y.sup.3 represents halogen 
are reacted with amides of the formula (IX) 
##STR12## 
in which A has the abovementioned meaning and 
R.sup.1 and R.sup.2 are identical or different and represent alkyl, or 
together with the nitrogen atom to which they are bonded represent a 3- to 
8-membered saturated heterocyclic ring, 
at temperatures from -80 to 20.degree. C., preferably -60 to -20.degree. 
C., 
if appropriate in the presence of a diuluent, preferably an aliphatic, 
alicyclic or aromatic hydrocarbon such as, for example, petroleum ether, 
hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene 
or decalin, or of an ether such as diethyl ether, diisopropyl ether, 
methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 
1,2-dimethoxyethane, 1,2-diethoxyethane or anisole and 
if appropriate in the presence of a base, preferably, an alkaline earth 
metal hydride or amide or alkali metal hydride or amide, such as, for 
example, sodium hydride or sodium amide, or of an alkali metal hydrocarbon 
compound or alkaline earth metal hydrocarbon compound, such as 
butyllithium. 
Formula (VIII) provides a general definition of the halogenophenyl 
compounds required as starting materials for carrying out Process a-3) 
according to the invention. In this formula (VIII), Y.sup.3 represents 
halogen, preferably bromine. 
The starting materials of the formula (VIII) are known, and/or they can be 
prepared by known methods (compare, for example, Synthesis 1987, 951). 
Formula (IX) provides a general definition of the amides furthermore 
required as starting materials for carrying out Process a-3) according to 
the invention. In this formula (IX), A preferably, or in particular, has 
the meaning which has already been given in connection with the 
description of the compounds of the formula (I) according to the invention 
as being preferred, or particularly preferred, for A. R.sup.1 and R.sup.2 
are identical or different and represent alkyl, preferably methyl, ethyl, 
n- or i-propyl or n-, i-, s- or t-butyl, or together with the nitrogen 
atom to which they are bonded represent a 3- to 8-membered saturated 
heterocyclic ring, preferably azetidinyl, pyrrolidinyl, morpholinyl, 
piperidinyl, hexahydroazepinyl. 
The starting materials of the formula (IX) are new and also an object of 
the present application. 
The amides of the formula (IX) are obtained when (Process a-4) oxamates of 
the general formula (X) 
##STR13## 
in which R.sup.1 and R.sup.2 have the abovementioned meanings and 
R.sup.3 represents alkyl, 
are first reacted with hydroxylamine or with an acid addition salt thereof, 
if appropriate in the presence of a diluent, preferably of an alcohol such 
as methanol, ethanol, n- or i-propanol, n-, i-, sec- or tert-butanol, 
ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene 
glycol monomethyl ether, diethylene glycol monethyl ether, 
and if appropriate in the presence of a base, preferably of an alkaline 
earth metal hydroxide, alcoholate, acetate, carbonate or hydrogen 
carbonate, such as, for example, sodium amide, sodium methoxide, sodium 
ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, 
sodium acetate, potassium acetate, calcium acetate, sodium carbonate, 
potassium carbonate, potassium hydrogen carbonate or sodium hydrogen 
carbonate, 
at temperatures from -20 to 50.degree. C., preferably 0 to 40.degree. C., 
and the resulting hydroxamic acid of the formula (XI) 
##STR14## 
with working up, is reacted with an alkylene derivative of the general 
formula (XII) 
EQU Y.sup.4 --A--Y.sup.5 (XII) 
in which 
A has the abovementioned meaning and 
Y.sup.4 and.sup.5 are identical or different and represent halogen, 
alkylsulphonyl or arylsulphonyl, 
if appropriate in the presence of a diluent, preferably of an alcohol, and 
if appropriate in the presence of a base, preferably of an alkaline earth 
metal hydroxide, alcoholate, acetate, carbonate or hydrogen carbonate, 
such as, for example, sodium amide, sodium methoxide, sodium ethoxide, 
potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodium 
acetate, potassium acetate, calcium acetate, sodium carbonate, potassium 
carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate. 
Formula (X) provides a general definition of the oxalamidates required as 
starting materials for carrying out the first step of process a-4) 
according to the invention. In this formula (X), R.sup.1 and R.sup.2 
preferably, or in particular, have those meanings which have already been 
given in connection with the description of the compounds of the formula 
(IX) according to the invention as being preferred, or particularly 
preferred for R.sup.1 and R.sup.2, R.sup.3 represents alkyl, preferably 
methyl or ethyl. 
The starting materials of the formula (X) are known, and/or they can be 
prepared by known methods (compare, for example, EP-A 469889) 
Hydroxylamine or salts thereof, which are further more required for 
carrying out the first step of Process a-4) according to the invention, 
are generally customary chemicals for synthesis. 
Formula (XII) provides a general definition of the alkylene derivatives 
required as starting materials for carrying out the second step of Process 
a-4) according to the invention. In this formula (XII), A preferably, or 
in particular, has the meaning which has already been given in connection 
with the description of the compounds of the formula (I) according to the 
invention as being preferred, or particularly preferred, for A. Y.sup.4 
and Y.sup.5 are identical or different and represent halogen, preferably 
chlorine or bromine; alkylsulphonyl, preferably methanesulphonyl; or 
arylsulphonyl, preferably toluenesulphonyl. 
Formula (III) provides a general definition of the halogenopyrimidines 
furthermore required as starting materials for carrying out Process a) 
according to the invention. In this formula (III), R, Q and X preferably, 
or in particular, have the meanings which have already been given in 
connection with the description of the compounds of the formula (I) 
according to the invention as being preferred, or particularly preferred, 
for R, Q and X. Y.sup.1 represents halogen, preferably fluorine or 
chlorine. 
The starting materials of the formula (III) are known, and/or they can be 
prepared by known methods (compare, for example, DE-A 4340181; Chem Ber., 
90 &lt;1957&gt;942, 951). 
Formula (IV) provides a general definition of the phenoxypyrimidines 
required as starting materials for carrying out Process b) according to 
the invention. In this formula (IV), A, E and X preferably, or in 
particular, have the meanings which have already been given in connection 
with the description of the compounds of the formula (I) according to the 
invention as being preferred, or particularly preferred, for A, E and X. 
Y.sup.2 represents halogen, preferably fluorine or chlorine. 
The starting materials of the formula (IV) are new and also the subject of 
the present invention. 
The phenoxypyrimidines of the general formula (IV) are obtained (Process 
b-1) when hydroxy compounds of the general formula (II) are reacted with a 
trihalogenopyrimidine of the general formula (XIII) 
##STR15## 
in which X, Y.sup.1 and Y.sup.2 are identical or different and represent 
in each case 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. 
The hydroxy compounds of the formula (II) required as starting materials 
for carrying out Process b-1) according to the invention have already been 
described in connection with the description of Process a) according to 
the invention. 
Formula (XIII) provides a general definition of the trihalogenopyrimidines 
furthermore required as starting materials for carrying out Process b-1) 
according to the invention. In this formula (XIII), X, Y.sup.1 and Y.sup.2 
represent halogen, preferably fluorine or chlorine. 
The trihalogenopyrimidines are known, and/or they can be prepared by known 
methods (compare, for example, Chesterfield et al., J. Chem Soc., 1955; 
3478, 3480). 
Formula (V) provides a general definition of the cyclic compounds 
furthermore required as starting materials for carrying out Process b) 
according to the invention. In this formula (V), R and Q preferably, or in 
particular, have the meanings which have already been given in connection 
with the description of the compounds of the formula (I) as being 
preferred, or particularly preferred, for R and Q. 
The cyclic compounds of the formula (V) are known chemicals for synthesis 
or can be prepared by simple methods. 
Diluents which are suitable for carrying out Processes a), b) and b1), 
according to the invention are all inert organic solvents. These 
preferably include ethers such as diethyl ether, diisopropyl ether, methyl 
t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 
1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as 
acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, amides 
such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, 
N-methylpyrrolidone or hexamethylphosphoric triamide; sulphoxides, such as 
dimethyl sulphoxide; or sulphones such as sulpholane. 
If appropriate, Processes a), b) and b-1) according to the invention are 
carried out in the presence of a suitable acid acceptor. Suitable acid 
acceptors are all customary inorganic or organic bases. These preferably 
include alkaline earth-metal hydrides, hydroxides, alcoholates, carbonates 
or hydrogen carbonates or alkali metal hydrides, hydroxides, alcoholates, 
carbonates or hydrogen carbonates such as, for example, sodium hydride, 
sodium amide, potassium tert-butoxide, sodium hydroxide, potassium 
hydroxide, sodium carbonate, potassium carbonate, potassium hydrogen 
carbonate or sodium hydrogen carbonate. 
Suitable catalysts for Processes a), b) and b-1) according to the invention 
are all copper(I) salts, such as, for example, copper(I) chloride, 
copper(I) bromide or copper(I) iodide. 
When carrying out Processes a), b) and b-1) according to the invention, the 
reaction temperatures can be varied within a substantial range. In 
general, the processes are carried out at temperatures from -20.degree. C. 
to 100.degree. C., preferably at temperatures from -10.degree. C. to 
80.degree. C. 
All the processes according to the invention are generally carried out 
under atmospheric pressure. However, it is also possible to carry out the 
processes under elevated or reduced pressure, in general between 0.1 bar 
and 10 bar. 
The reaction is carried out and the reaction products are worked up and 
isolated by generally customary methods (compare also the preparation 
examples). 
The active compounds according to the invention have a powerful 
microbicidal activity and can be employed in practice for controlling 
undesirable microorganisms. The active compounds are suitable for use as 
crop protection agents, in particular as fungicides. 
Fungicidal agents are employed in crop protection for controlling 
Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, 
Ascomycetes, Basidiomycetes and Deuteromycetes. 
Bactericidal agents are employed in crop protection for controlling 
Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and 
Streptomycetaceae. 
Some pathogens causing fungal and bacterial diseases which come under the 
generic names listed above may be mentioned as examples, but not by way of 
limitation. 
Xanthomonas species, such as, for example, Xanthomonas campestris pv. 
oryzae; 
Pseudomonas species, such as, for example, Pseudomonas syringae pv. 
lachrymans; 
Erwinia species, such as, for example, Erwinia amylovora; 
Pythium species, such as, for example, Pythium ultimum; 
Phytophthora species, such as, for example, Phytophthora infestans; 
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli, 
or Psudoperonospora cubensis; 
Plasmopara species, such as, for exampsle, Plasmopara viticola; 
Bremia species, such as, for example, Bremia lactucae 
Peronospora species, such as, for example, Peronospora pisi or P. 
brassicae; 
Erysiphe species, such as, for example, Erysiphe graminis; 
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea; 
Podosphaera species, such as, for example, Podosphaera leucotricha; 
Venturia species, such as, for example, Venturia inaequalis; 
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea 
(conidia form: Drechslera, syn: Helminthosporium); 
Cochliobolus species, such as, for example, Cochliobolus sativus (conidia 
form: Drechslera, syn: Helminthosporium); 
Uromyces species, such as, for example, Uromyces appendiculatus; 
Puccinia species, such as, for example, Puccinia recondita; 
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum; 
Tilletia species, such as, for example, Tilletia caries; 
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae; 
Pellicularia species, such as, for example, Pellicularia sasakii; 
Pyricularia species, such as, for example, Pyricularia oryzae; 
Fusarium species, such as, for example, Fusarium culmorum; 
Botrytis species, such as, for example, Botrytis cinerea; 
Septoria species, such as, for example, Septoria nodorum; 
Leptosphaeria species, such as, for example, Leptosphaeria nodorum; 
Cercospora species, such as, for example, Cercospora canescens; 
Alternaria species, such as, for example, Alternaria braccicae and 
Pseudocercosporella species, such as, for example, Pseudocercosporella 
herpotrichoides. 
The fact that the active compounds are well tolerated by plants at the 
concentrations required for controlling plant diseases permits the 
treatment of aerial parts of plants, of propagation stock and seeds, and 
of the soil. 
The active compounds are employed particularly successfully for controlling 
cereal diseases, such as, for example, against Erysiphe, Fusarium, 
Pseudocercosporella and Puccinia species, or for controlling diseases in 
viticulture or fruit and vegetable production, such as, for example, 
against Venturai, Sphaerotheca, Phytophthora and Plasmopara species, or 
else for controlling rice diseases, such as, for example, Pyricularia 
species. Furthermore, the active compounds according to the invention have 
a very powerful and broad in-vitro activity. 
Depending on their particular physical and/or chemical properties, the 
active compounds can be converted into the customary formulations, such as 
solutions, emulsions, suspensions, powdeers, foams, pastes, granules, 
aerosols, microencapsulations in polymeric substances and in coating 
compositions for seed, or else ULV cold- and hot-fogging formulations. 
These formulations are produced in a known manner, for example by mixing 
the active compounds with extenders, that is, liquid solvents, liquefield 
gases under pressure, and/or solid carriers, optionally with the use of 
surface-active agents, that is, emulsifiers and/or dispersants, and/or 
foam formers. In the case of the use of water as an extender, organic 
solvents can, for example, also be used as auxiliary solvents. The 
following are mainly suitable as liquid solvents: aromatics such as 
xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated 
aliphatic hydrocarbons such as chlorobenzens, chloroethylenes or methylene 
chloride, aliphatic hydrocarbons such as cyclohexane or parafffins, for 
example mineral oil fractions, alcohols such as butanol or glycol and 
their ethers and esters, ketones such as acetone, methyl ethyl ketone, 
methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as 
dimethylformamide and dimethyl sulphoxide, or else water. Liquefied 
gaseous extenders or carriers are to be understood as meaning liquids 
which are gaseous at ambient temperature and under atmospheric pressure, 
for example aerosol propellants such as halogenohydrocarbons, or else 
butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are 
for example ground natural minerals such as kolins, clays, talc, chalk, 
quartz, attapulgite, montmorillonite or diatomaceous earth, and ground 
synthetic minerals such as highly-disperse silica, alumina and silicates. 
Suitable solid carriers for granules are for example crushed and 
fractionated natural rocks such as calcite, marble, pumice, sepiolite and 
dolomite, or else synthetic granules of inorganic and organic meals, and 
granules of organic material such as sawdust, coconut shells, maize cobs 
and tobacco stalks. Suitable emulsifiers and/or foam formers, are for 
example nonionic and anionic emulsifiers such as polyoxyethylene fatty 
acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl 
polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, or 
else protein hydrolysates. Suitable dispersants are: for example 
lignin-sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, or else natural phospholipids such as 
cephalins and lecithins and synthetic phospholipids can be used in the 
formulations. Other additives can be mineral and vegetable oils. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian blue, and organic dyestuffs such 
as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, 
and trace nutrients such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations generally comprise between 0.1 and 95 per cent by weight 
of active compound, preferably between 0.5 and 90%. 
The active compounds according to the invention, as such or in their 
formulations can also be used as a mixture with known fungicides, 
bactericides, acaricides, nematicides or insecticides, for example to 
widen the spectrum of action or to prevent the build-up of resistance. In 
many cases, synergistic effects are obtained, i.e. the activity of the 
mixture is greater than the activity of the individual components. 
Examples of particularly advantageous mixtures are the following compounds. 
Fungicides: 
2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 
2',6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro-methyl-1,3-thizole 
-5-carboxanilide; 2,6-dichloro-N-(4-trifluoromethylbenzl)benzamide; 
(E)-2-methoxyimino-N-methyl-2-(2-phenoxyphenyl)acetamide; 
8-hydroxyquinoline sulphate; methyl 
(E)-2-{2-[6-(2-cyanophenoxy)-pyrimidin-4-yloxy]-phenyl}-3-methoxyacrylate; 
methyl (E)-methoximino[alpha-(o-tolyloxy)-o-tolyl]acetate; 2-phenylphenol 
(OPP), aldimorph, ampropylfos, anilazine, azaconazole, 
benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, 
blasticidin-S, bromoconazole, bupirimate, buthiobate, 
calcium polysulphide, captafol, captan, carbendazim, carboxin, 
quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, 
cufraneb, cymoxanil, cyproconazole, cyprofuram, 
dichlorophen, diclobutrazol, diclofluanid, diclomezin, dicloran, 
diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, 
dinocap, diphenylamine, dipyrithion, ditalimfos, dithianon, dodine, 
drazoxolon, 
edifenphos, epoxyconazole, ethirimol, etridiazole, 
fenarimol. fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, 
fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, 
fluazinam, fludioxonil, fluoromide, fluquinconazole, flusilazole, 
flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminium, fthalide, 
fuberidazole, furalaxyl, furmecyclox, 
guazatine, 
hexachlorobenzene, hexaconazole, hymexazol, 
imazalil, imibenconazole, iminoctadine, iprobenfos (IBP), iprodione, 
isoprothiolane, kasugamycin, copper preparations such as: copper 
hydroxide, copper naphthenate, copper oxychloride, copper sulphate, copper 
oxide, oxine-copper and Bordeaux mixture, mancopper, mancozeb, maneb, 
mepanipyrim, 
mepronil, metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram, 
metsulfovax, myclobutanil, 
nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol, 
ofurace, oxadixyl, oxamocarb, oxycarboxin, 
pefurazoate, penconazole, pencyuron, phosdiphen, pimaricin, piperalin, 
polyoxin, probenazole, prochloraz, procymidone, propamocarb, 
propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, 
quintozene (PCNB), 
sulphur and sulphur preparations, 
tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, 
thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, 
triadimefon, triadimenol, triazoxide, trichlamide, tricyclazole, 
tridemorph, triflumizole, triforine, triticonazole, 
validamycin A, vinclozolin, 
zineb, ziram. 
Bactericides: 
bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, 
kasugamycin, octhilinone, furanecarboxylic acid, oxytetracyclin, 
probenazole, streptomycin, tecloftalam, copper sulphate and other copper 
preparations. 
Insecticides/Acaricides/Nematicides: 
abamectin, acephate, acrinathrin, alanycarb, aldicarb, alphamethrin, 
amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, azinphos M, 
azocyclotin, 
Bacillus thuringiensis, 
4-bromo-2-(4-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole 
-3-carbonitrile, bendiocarb, benfuracarb, bensultap, betacyfluthrin, 
bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, 
butocarboxin, butylpyridaben, 
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan, cartap, 
chloethocarb, chloroethoxyfos, chlorofenvinphos, chlorofluazuron, 
chloromephos, 
N-[(6-chloro-3-pyridinyl)-methyl]-N'-cyano-N-methyl-ethanimidamide, 
chloropyrifos, chloropyrifos M, cis-resmethrin, clocythrin, clofentezine, 
cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, 
cypermethrin, cyromazine, 
deltamethrin, demeton-M, demeton-S, demeton-S-methyl, difenthiuron, 
diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, 
diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton, 
edifenphos, emamectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, 
ethoprophos, etrimphos, 
fenamiphos, fenzaquin, fenbutatin oxide, fenitrothion, fenobucarb, 
fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, 
fenthion, fenvalerate, fipronil, fluazinam, fluazuron, flucycloxuron, 
flucythrinate, flufenoxuron, flufenprox, fluvalinate, fonophos, 
formothion, fosthiazate, fubfenprox, furathiocarb, 
HCH, heptenophos, hexaflumuron, hexythiazox, 
imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, 
ivermectin, 
lambda-cyhalothrin, lufenuron, 
malathion, mecarbam, mevinphos, mesulfenphos, metaldehyde, methacrifos, 
methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, 
monocrotophos, moxidectin, 
naled, NC 184, nitenpyram, 
omethoate, oxamyl, oxydemethon M, oxydeprofos, 
parathion A, parathion M, permethrin, phenthoate, phorate, phosalone, 
phosmet, phosphamidon, phoxim, pirimicarb, pirimiphos M, pirimiphos A, 
profenofos, promecarb, propaphos, propoxur, prothiofos, prothoate, 
pymetrozin, pyrachlophos, pyridaphenthion, pyresmethrin, pyrethrum, 
pyridaben, pyrimidifen, pyriproxifen, 
quinalphos, 
salithion, sebufos, silafluofen, sulfotep, sulprofos, 
tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, 
temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, 
thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, triarathen, 
triazophos, triazuron, trichlorfon, triflumuron, trimethacarb, 
vamidothion, XMC, xylylcarb, zetamethrin. 
A mixture with other known active compounds, such as herbicides or with 
fertilizers or growth regulators is also possible. 
The active compounds can be used as such, in the form of their commercially 
available formulations or the use forms prepared therefrom, such as 
read-to-use solutions, suspensions, wettable powders, pastes, soluble 
powders, dusts and granules. They are used in the customary manner, for 
example by pouring, spraying, atomizing, scattering, foaming, brushing on 
and the like. It is also possible to apply the active compounds by the 
ultra-low volume method, or to inject the active compound formulation or 
the active compound itself into the soil. The seed of the plants can also 
be treated. 
In the treatment of parts of plants, the active compound concentrations in 
the use forms can be varied within a substantial range: They are, in 
general, between 1 and 0.0001% by weight, preferably between 0.5 and 
0.001% by weight. 
In the treatment of seed, amounts of active compound of 0.001 to 50 g per 
kilogram of seed, preferably 0.01 to 10 g, are generally required. 
For the treatment of soil, active compound concentrations of 0.00001 to 
0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the 
site of action.