The invention relates to novel substituted arylazadioxacycloalkenes, a plurality of processes for their preparation and to their use as fungicides.

The invention relates to novel substituted arylazadioxacycloalkenes, a 
plurality of processes for their preparation and to their use as 
fungicides. 
Certain substituted arylazadioxacycloalkenes are known to have fungicidal 
properties cf. Hokko Chemical Industry, JP-A 02001484; cited in Chem. 
Abstr. 113:6381 (1990)!. 
However, in many instances the activity of these compounds is 
unsatisfactory. 
This invention, accordingly, provides the novel substituted 
arylazadioxacycloalkenes of 
##STR1## 
in which A represents optionally substituted alkylene. 
Ar.sup.1, Ar.sup.2 independently of one another each represent optionally 
substituted arylene or heteroarylene. 
E represents a 1-alkene-1,1-diyl grouping which contains a radical R.sup.1 
in position 2, or represents a 2-aza-1-alkene-1,1-diyl grouping which 
contains a radical R.sup.2 in position 2, or represents an optionally 
substituted imino grouping ("azamethylene", N--R.sup.3), or represents a 
3-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in 
position 1 and a radical R.sup.5 in position 3, or represents a 
3-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in 
position 1, or represents a 3-thia-1-propene-2,3-diyl grouping which 
contains a radical R.sup.4 in position 1, or represents a 
1-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.6 in 
position 1 and a radical R.sup.5 in position 3, or represents a 
1-aza-1-propene-2,3-diyl grouping which contains a radical R.sup.4 in 
position 1 and a radical R.sup.5 in position 3, or represents a 
1,3-diaza-1-propene -2,3-diyl grouping which contains a radical R.sup.6 in 
position 1 and a radical R.sup.5 in position 3, or represents a 
1-aza-3-oxa-1-propene-2,3-diyl grouping which contains a radical R.sup.6 
in position 1, or represents a 1-aza-3-thia-1-propene -2,3-diyl grouping 
which contains a radical R.sup.6 in position 1, where 
R.sup.1, R.sup.4 each represent hydrogen, halogen, cyano or respectively 
optionally substituted alkyl, alkoxy, alkylthio, alkylamino or 
dialkylamino, 
R.sup.2, R.sup.6 each represent hydrogen, amino, cyano or respectively 
optionally substituted alkyl, alkoxy, alkylamino or dialkylamino, and 
R.sup.3 represents hydrogen, cyano or respectively optionally substituted 
alkyl, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl, 
R.sup.5 represents alkyl, 
G represents a single bond, represents oxygen, sulphur, or represents 
respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or 
cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl or one of the 
groupings below 
--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 
--, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, 
--N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, 
--S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, 
--C(R.sup.7)----N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, 
--N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 
--, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, 
--CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, 
--Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, 
--N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, O--CH.sub.2 
--C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7)--N--O--, --T--Ar.sup.3 --or 
--T--Ar.sup.3 --Q--, where 
Ar.sup.3 represents optionally substituted arylene, heteroarylene, 
cycloalkylene or heterocycloalkylene (i.e. an aliphatic ring which is 
attached twice and in which one or more carbon atoms are replaced by 
hetero atoms, i.e. by atoms different from carbon), 
n represents the numbers 0, 1 or 2, 
Q represents oxygen or sulphur, 
R.sup.7 represents hydrogen, cyano or respectively optionally substituted 
alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and 
R.sup.8 represents hydrogen, hydroxyl, cyano or respectively optionally 
substituted alkyl, alkoxy or cycloalkyl and 
T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, 
CH.sub.2 --S-- or represents optionally substituted alkanediyl and 
R represents alkyl, alkoxy, hydroxylamino, alkoxamino, alkylamino or 
dialkylamino. 
Furthermore, it has been found that the novel substituted 
arylazadioxacycloalkenes of the general formula (I) are obtained when 
a) hydroxyl compounds of the general formula (II) 
##STR2## 
in which A and Ar.sup.2 are each as defined above, are reacted with 
halogen compounds of the general formula (III) 
##STR3## 
in which G.sup.2 represents --Ar.sup.3 --Q-- or represents --Ar--, 
Ar.sup.1, Ar.sup.3, E, Q and R are each as defined above and 
X represents halogen, 
if appropriate in the presence of an acid acceptor and if appropriate in 
the presence of a diluent; 
b) hydroxyl compounds of the general formula (II) 
##STR4## 
in which A and Ar.sup.2 are each as defined above, are reacted with 
halogen compounds of the general formula (IV) 
##STR5## 
in which Ar.sup.1, E and R are each as defined above and 
X represents halogen, 
if appropriate in the presence of an acid acceptor and if appropriate in 
the presence of a diluent; 
c) esters of the general formula (I-1) 
##STR6## 
in which A, Ar.sup.1, Ar.sup.2, E and G are each as defined above and 
A.sup.1 represents alkyl, are reacted with amines of the general formula 
(V), 
##STR7## 
in which A.sup.2 and A.sup.3 independently of one another are each 
hydrogen, respectively optionally substituted alkyl, alkoxy or hydroxyl, 
or an acid addition complex thereof 
if appropriate in the presence of an acid acceptor and if appropriate in 
the presence of a diluent. 
Finally, it has been found that the novel substituted carboxamides of the 
general formula (I) have a very strong fungicidal activity. The compounds 
according to the invention may optionally be present as mixtures of 
various possible isomeric forms, in particular of stereoisomers, such as, 
for example, 
E- and Z-isomers. Both the E- and the Z-isomers, and any mixtures of these 
isomers, are claimed. 
The invention preferably relates to compounds of the formula (I) in which 
A represents alkylene having 1 to 4 carbon atoms, 
Ar.sup.1 represents respectively optionally substituted phenylene or 
naphthylene, represents mono- or dicyclic heteroarylene having in each 
case 5 or 6 ring members or represents benzo-fused heteroarylene having 5 
or 6 ring members, at least one of which in each case is oxygen, sulphur 
or nitrogen and one or two more of which optionally are nitrogen, the 
possible substituents preferably being selected from the list below: 
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, 
thiocarbamoyl, respectively straight-chain or branched alkyl, alkoxy, 
alkylthio, alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 
carbon atoms, respectively straight-chain or branched alkenyl, alkenyloxy 
or alkinyloxy having in each case 2 to 6 carbon atoms, respectively 
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, respectively straight-chain or branched halogenoalkenyl or 
halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 
identical or different halogen atoms, respectively straight-chain or 
branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy, 
alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalkyl or alkoximinoalkyl 
having in each case 1 to 6 carbon atoms in the individual alkyl moieties, 
alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms, is 
attached twice and is optionally mono- or polysubstituted by identical or 
different substituents from the group consisting of halogen, 
straight-chain or branched alkyl having 1 to 4 carbon atoms and 
straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 
to 9 identical or different halogen atoms, 
Ar.sup.2 represents phenylene or naphthylene or represents heteroarylene 
having 3 to 7 ring members, each of the radicals being optionally mono- or 
polysubstituted by identical or different substituents and at least one of 
the 3 to 7 ring members being oxygen, sulphur or nitrogen and one or two 
more optionally being nitrogen, the possible substituents preferably being 
selected from the list below: 
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, 
thiocarbamoyl; 
respectively straight-chain or branched alkyl, alkoxy, alkylthio, 
alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms; 
respectively straight-chain or branched alkenyl or alkenyloxy having in 
each case 2 to 6 carbon atoms; 
respectively 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; 
respectively straight-chain or branched halogenoalkenyl or 
halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 
identical or different halogen atoms; 
respectively straight-chain or branched alkylamino, dialkylamino, 
alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, 
hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon 
atoms in the individual alkyl moieties; 
alkylene or dioxyalkylene, each of which has 1 to 6 carbon atoms, is 
attached twice and is optionally mono- or polysubstituted by identical or 
different substituents from the group consisting of halogen, 
straight-chain or branched alkyl having 1 to 4 carbon atoms and 
straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 
to 9 identical or different halogen atoms; 
cycloalkyl having 3 to 6 carbon atoms; 
E represents one of the groupings below: 
##STR8## 
in which R.sup.1 represents hydrogen, halogen, cyano or represents 
respectively optionally halogen-, cyano- or C.sub.1 -C.sub.4 
-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino 
having in each case 1 to 6 carbon atoms in the alkyl radicals, 
R.sup.2 represents hydrogen, amino, cyano or represents respectively 
optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, 
alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms 
in the alkyl radicals, 
R.sup.3 represents hydrogen, cyano or represents respectively optionally 
halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkenyl or 
alkinyl having in each case up to 6 carbon atoms or represents 
respectively optionally halogen-, cyano-, carboxyl-, C.sub.1 -C.sub.4 
-alkyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted cycloalkyl or 
cycloalkylalkyl having 3 to 6 carbon atoms in the cycloalkyl moieties and 
optionally 1 to 4 carbon atoms in the alkyl moiety, 
R.sup.4 represents hydrogen, halogen, cyano or represents respectively 
optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, 
alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 
carbon atoms in the alkyl radicals, 
R.sup.5 represents alkyl having 1 to 6 carbon atoms and 
R.sup.6 represents hydrogen, amino, cyano or represents respectively 
optionally halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, 
alkoxy, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms 
in the alkyl radicals; 
G represents a single bond, represents oxygen, sulphur or represents 
respectively optionally halogen-, hydroxyl-, C.sub.1 -C.sub.4 -alkyl-, 
C.sub.1 -C.sub.4 -halogenoalkyl- or C.sub.3 -C.sub.6 
-cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl having in each 
case up to 4 carbon atoms or one of the groupings below 
--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 
--, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, 
--N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n,--, --CQ--, 
--S(O)n--CH.sub.2 --, --C(R.sup.7).dbd.N--O--, --C(R7).dbd.N--O--CH.sub.2 
--, --N(R.sup.8)--, --CQ--N(R.sup.8)--, --N(R.sup.8)--CQ--, 
--Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 --, --CH.sub.2 
--O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, --CQ--N(R.sup.8)--CQ--Q--, 
--N(R.sup.8)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, 
--N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 
--C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 
or --T--A.sup.3 --Q--, where 
n represents the numbers 0, 1 or 2, 
Q represents oxygen or sulphur, 
R.sup.7 represents hydrogen, cyano, represents respectively optionally 
halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl, alkoxy, 
alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon 
atoms in the alkyl groups, or represents respectively optionally halogen-, 
cyano-, carboxyl-, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 
-alkoxy-carbonyl-substituted cycloalkyl having 3 to 6 carbon atoms, and 
R.sup.8 represents hydrogen, hydroxyl, cyano or represents optionally 
halogen-, cyano- or C.sub.1 -C.sub.4 -alkoxy-substituted alkyl having 1 to 
6 carbon atoms, or represents optionally halogen-, cyano-, carboxyl-, 
C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-carbonyl-substituted 
cycloalkyl having 3 to 6 carbon atoms and 
Ar.sup.3 represents phenylene, naphthylene, cycloalkylene or represents 
heteroarylene or heterocycloalkylene having 3 to 7 ring members, each of 
the radicals being optionally mono- or polysubstituted by identical or 
different substituents and at least one of the 3 to 7 ring members being 
oxygen, sulphur or nitrogen and one or two more optionally being nitrogen, 
the possible substituents preferably being selected from the list below: 
halogen, cyano, nitro, amino, hydroxyl, formyl, carboxyl, carbamoyl, 
thiocarbamoyl; 
respectively straight-chain or branched alkyl, alkoxy, alkylthio, 
alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atoms; 
respectively straight-chain or branched alkenyl or alkenyloxy having in 
each case 2 to 6 carbon atoms; 
respectively 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; 
respectively straight-chain or branched halogenoalkenyl or 
halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 
identical or different halogen atoms; 
respectively straight-chain or branched alkylamino, dialkylamino, 
alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, 
hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon 
atoms in the individual alkyl moieties, and; 
cycloalkyl having 3 to 6 carbon atoms and 
T represents a single bond, represents oxygen, sulphur --CH.sub.2 --O--, 
CH.sub.2 --S-- or represents alkanediyl having 1 to 3 carbon atoms, 
R represents alkyl, alkoxy, alkylamino, hydroxylamino, alkoxyamino or 
dialkylamino having in each case 1 to 4 carbon atoms. 
In the definitions, the saturated or unsaturated hydrocarbon chains, such 
as alkyl, alkanediyl, alkenyl, or alkinyl are in each case, even in 
combination with hetero atoms, such as in alkoxy, alkylthio or alkylamino, 
straight-chain or branched. 
Halogen generally represents fluorine, chlorine, bromine or iodine, 
preferably fluorine, chlorine or bromine, in particular fluorine or 
chlorine. 
The invention relates in particular to compounds of the formula (I) in 
which 
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,1-, 1,2-, 1,3- or 
2,2-propylene, 1,1-, 1,2-, 1,3-, 1,4-, 2,2-, 2,3-butylene or 1,1-, 1,2- or 
1,3-i-butylene, 
Ar.sup.1 represents respectively optionally substituted ortho-, meta- or 
para-phenylene, represents furanediyl, thiophenediyl, pyrrolediyl, 
pyrazolediyl, triazolediyl, oxazolediyl, isoxazolediyl, thiazolediyl, 
isothiazolediyl, oxadiazolediyl, thiadiazolediyl, pyridinediyl (in 
particular pyridine-2,3-diyl), pyrimidinediyl, pyridazinediyl, 
pyrazinediyl, 1,3,4-triazinediyl or 1,2,3-triazinediyl, the possible 
substituents in particular being selected from the list below: 
fluorine, chlorine, cyano, methyl, ethyl, cyclopropyl, trifluoromethyl, 
methoxy, ethoxy, methylthio, methylsulphinyl or methylsulphonyl, 
Ar.sup.2 represents phenylene, naphthylene, furanediyl, thiophenediyl, 
oxazolediyl, isoxazolediyl, thiazolediyl, isothiazolediyl, 
1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, 1,2,4-thiadiazolediyl, 
1,3,4-thiadiazolediyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, 
pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl, 1,3,5-triazinediyl, 
each of which is optionally mono- to trisubstituted by identical or 
different substituents, the possible substituents preferably being 
selected from the list below: 
fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, 
carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, 
ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, 
methylsulphonyl or ethylsulphonyl, trifluoromethyl, difluoromethoxy, 
trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, 
difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, 
trifluoromethylsulphinyl or trifluoromethylsulphonyl, methylamino, 
ethylamino, n- or i-propylamino, dimethylamino, diethylamino, acetyl, 
propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, 
ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, 
ethoximinomethyl, methoximinoethyl or ethoximinoethyl; 
E represents one of the groupings below: 
##STR9## 
in which R.sup.1 represents hydrogen, fluorine, chlorine, bromine, cyano 
or represents respectively optionally fluorine-, chlorine-, cyano-, 
methoxy- or ethoxy- substituted methyl, ethyl, propyl, methoxy, ethoxy, 
methylthio, ethylthio, methylamino, ethylamino or dimethylamino, 
R.sup.2 represents hydrogen, amino, cyano or represents respectively 
optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted 
methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, 
R.sup.3 represents hydrogen, cyano or represents respectively optionally 
fluorine-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or 
i-propyl, n-, i- or s-butyl, represents allyl or propargyl or represents 
respectively optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, 
ethyl-, n- or i-propyl-, methoxy-carbonyl- or ethoxy-carbonyl-substituted 
cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 
cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, 
R.sup.4 represents hydrogen, fluorine, chlorine, bromine, cyano or 
represents respectively optionally fluorine-, chlorine-, cyano-, methoxy- 
or ethoxy- substituted methyl, ethyl, propyl, methoxy, ethoxy, methylthio, 
ethylthio, methylamino, ethylamino or dimethylamino, 
R.sup.5 represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, 
R.sup.6 represents hydrogen, amino, cyano or represents respectively 
optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted 
methyl, ethyl, methoxy, ethoxy, methylamino, ethylamino or dimethylamino, 
and 
G represents a single bond, represents oxygen, sulphur, or represents 
respectively optionally fluorine-, chlorine-, bromine-, hydroxyl-, 
methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, cyclopropyl-, 
cyclobutyl-, cyclopentyl- or cyclohexyl-substituted methylene, dimethylene 
(ethane-1,2-diyl), ethene-1,2-diyl, ethine-1,2-diyl or one of the 
groupings below 
--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 
--, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, 
--N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, 
--S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, 
--C(R7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, 
--N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 
--, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, 
--CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, 
--Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, 
--N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 
--C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 
-- or --T--Ar.sup.3 --Q--, where 
n represents the numbers 0, 1 or 2, 
Q represents oxygen or sulphur, 
R.sup.7 represents hydrogen, cyano, represents respectively optionally 
fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted methyl, 
ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, propoxy, 
butoxy, methylthio, ethylthio, propylthio, butylthio, methylamino, 
ethylamino, propylamino, dimethylamino or diethylamino or represents 
respectively optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, 
ethyl-, n- or i-propyl-, methoxycarbonyl- or ethoxy-carbonyl-substituted 
cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, and 
R.sup.8 represents hydrogen, hydroxyl, cyano or represents respectively 
optionally fluorine-, chlorine-, cyano-, methoxy- or ethoxy-substituted 
methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl or represents 
respectively optionally fluorine-, chlorine-, cyano-, carboxyl-, methyl-, 
ethyl-, n- or i-propyl-, methoxy-carbonyl- or ethoxy-carbonyl-substituted 
cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, 
Ar.sup.3 represents phenylene, naphthylene, furanediyl, thiophenediyl, 
oxazolediyl, isoxazolediyl, thiazolediyl, isothiazolediyl, 1 
,2,4-oxadia-zolediyl, 1,3,4-oxadiazolediyl, 1,2,4-thiadiazolediyl, 
1,3,4-thiadiazolediyl, pyridinediyl, pyrimidinediyl, pyridazinediyl, 
pyrazinediyl, 1,2,3-triazinediyl, 1,2,4-triazinediyl, 1,3,5-triazinediyl, 
oxiranediyl, oxetanediyl, tetrahydrofuranediyl, perhydropyranediyl or 
pyrrolidinediyl, each of which is optionally mono- to trisubstituted, the 
possible substituents preferably being selected from the list below: 
fluorine, chlorine, bromine, cyano, nitro, amino, hydroxyl, formyl, 
carboxyl, carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, 
trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, 
difluoromethylthio, difluorochloromethylthio, trifluoromethylthio, 
trifluoromethylsulphinyl or trifluoromethylsulphonyl, , acetyl, propionyl, 
acetyloxy, methoxycarbonyl, ethoxycarbonyl, methylsulphonyloxy, 
ethylsulphonyloxy, hydroximinomethyl, hydroximinoethyl, methoximinomethyl, 
ethoximinomethyl, methoximinoethyl, ethoximinoethyl or cyclopropyl and 
T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, 
CH.sub.2 --S--, methylene, ethylene or propylene and 
R represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or 
i-propoxy, methylamino, ethylamino, n- or i-propylamino, hydroxylamino, 
methoxyamino, dimethylamino, diethylamino. 
Very particular preference is given to compounds of the general formula (I) 
in which 
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene, 
Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or 
thiophene-2,3-diyl, 
Ar.sup.2 represents phenylene which is in each case optionally mono- to 
trisubstituted by identical or different substituents, the possible 
substituents preferably being selected from the list below: 
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, 
difluorochloromethoxy, trifluoroethoxy, difluomethylthio, 
trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or 
trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, 
methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, 
methylenedioxy or ethylenedioxy, each of which is attached twice and each 
of which is optionally mono- to tetrasubstituted by identical or different 
substituents from the group consisting of fluorine, chlorine, methyl, 
trifluoromethyl or ethyl, 
E represents one of the groupings below 
##STR10## 
in which R.sup.1 and R.sup.2 each represent methoxy and 
R.sup.3 represents hydrogen, cyano, methyl, ethyl, n- or i-propyl, methoxy 
or ethoxy, 
G represents oxygen or represents respectively optionally fluorine-, 
chlorine- or bromine-substituted dimethylene (ethane-1,2-diyl), ethene- 
1,2-diyl or one of the groupings below 
--Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--; --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 
--, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, 
--N.dbd.N--, --S(O).sub.n ----CH.sub.2 --S(O).sub.n --, --CQ--, 
--S(O).sub.n --CH.sub.2 --, --C(R.sup.7).dbd.N--O--, 
--C(R.sup.7).dbd.N--O--CH.sub.2 --, --N(R.sup.8)--, --CQ--N(R.sup.8)--, 
--N(R.sup.8)--CQ--, --Q--CQ--N(R.sup.8)--, --N.dbd.C(R.sup.7)--Q--CH.sub.2 
--, --CH.sub.2 --O--N.dbd.C(R.sup.7)--, --N(R.sup.8)--CQ--Q--, 
--CQ--N(R.sup.8)--CQ--Q--, --N(R.sup.8)--CQ--Q--CH.sub.2 --, 
--Q--C(R.sup.7).dbd.N--O--CH.sub.2 --, 
--N(R.sup.8)--C(R.sup.7).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 
--C(R.sup.7).dbd.N--O--, --N.dbd.N--C(R.sup.7).dbd.N--O--, --T--Ar.sup.3 
--or --T--Ar.sup.3 --Q--, where 
n represents the numbers 0, 1 or 2, 
Q represents oxygen or sulphur, 
R.sup.7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl, and 
R.sup.8 represents hydrogen, methyl, ethyl or cyclopropyl, 
Ar.sup.3 represents phenylene, 1,2,4-thiadiazolediyl, 
1,3,4-thiadiazolediyl, 1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl, 
pyridinediyl, pyrimidinediyl, pyridazinediyl, pyrazinediyl, 
1,2,3-triazinediyl, 1,2,4-triazinediyl- or 1,3,5-triazinediyl, each of 
which is optionally mono- to trisubstituted by identical or different 
substituents, the possible substituents preferably being selected from the 
list below: 
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, 
cyclopropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, 
trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, 
difluoromethylthio, trifluoromethylthio, difluorochloromethylthio, 
trifluoromethylsulphinyl or trifluoromethylsulphonyl, and 
T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, 
CH.sub.2 --S--, methylene, ethylene or propylene and 
R represents methyl, ethyl, methoxy, methylamino or hydroxylamino. 
A particularly preferred group of compounds according to the invention are 
those compounds of the formula (I) 
in which 
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene, 
Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or 
thiophene-2,3-diyl, 
Ar.sup.2 represents phenylene which is in each case optionally mono- to 
trisubstituted by identical or different substituents, the possible 
substituents preferably being selected from the list below: 
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, 
difluorochloromethoxy, trifluoroethoxy, difluomethylthio, 
trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or 
trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, 
methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, 
methylenedioxy or ethylenedioxy, each of which is attached twice and each 
of which is optionally mono- to tetrasubstituted by identical or different 
substituents from the group consisting of fluorine, chlorine, methyl, 
trifluoromethyl or ethyl, 
E represents one of the groupings below 
##STR11## 
in which R.sup.1 and R.sup.2 each represent methoxy and 
G represents --O--CH.sub.2 and 
R represents methyl, ethyl, methoxy, methylamino or hydroxylamino. 
Also very particularly preferred are compounds of the general formula (I) 
in which 
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene, 
Ar.sup.1 represents ortho-phenylene, pyridine-2,3-diyl or 
thiophene-2,3-diyl, 
Ar.sup.2 represents phenylene which is in each case optionally mono- to 
trisubstituted by identical or different substituents, the possible 
substituents preferably being selected from the list below: 
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, 
difluorochloromethoxy, trifluoroethoxy, difluomethylthio, 
trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or 
trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, 
methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, 
methylenedioxy or ethylenedioxy, each of which is attached twice and each 
of which is optionally mono- to tetrasubstituted by identical or different 
substituents from the group consisting of fluorine, chlorine, methyl, 
trifluoromethyl or ethyl, 
E represents one of the groupings below 
##STR12## 
in which R.sup.1 and R.sup.2 each represent methoxy and 
G represents --C(R7).dbd.N--O--CH.sub.2 --where 
R.sup.7 represents hydrogen, cyano, methyl, ethyl or cyclopropyl and 
R represents methyl, ethyl, methoxy, methylamino or hydroxylamino. 
Furthermore, very particular preference is given to compounds of the 
general formula 
in which 
A represents methylene, 1,1-ethylene, 1,2-ethylene, 1,2- or 1,3-propylene, 
Ar.sup.1 represents ortho-phenylene, 
Ar.sup.2 represents phenylene which is in each case optionally mono- to 
trisubstituted by identical or different substituents, the possible 
substituents preferably being selected from the list below: 
fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, i-, 
s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- 
or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or 
ethylsulphonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, 
difluorochloromethoxy, trifluoroethoxy, difluomethylthio, 
trifluoromethylthio, difluorochloromethylthio, trifluoromethylsulphinyl or 
trifluoromethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, 
methoximinomethyl, ethoximinomethyl, methoximinoethyl, ethoximinoethyl, 
methylenedioxy or ethylenedioxy, each of which is attached twice and each 
of which is optionally mono- to tetrasubstituted by identical or different 
substituents from the group consisting of fluorine, chlorine, methyl, 
trifluoromethyl or ethyl, 
E represents one of the groupings below: 
##STR13## 
in which R.sup.1 and R.sup.2 each represent methoxy, 
G represents --T--Ar--Q--where 
Q represents oxygen or sulphur, 
Ar.sup.3 represents 1 ,2,4-thiadiazolediyl, 1,3 ,4-thiadiazolediyl, 
1,2,4-oxadiazolediyl, 1,3,4-oxadiazolediyl or represents pyridinediyl, 
pyrimidinediyl or 1,3,5-triazinediyl, each of which is optionally mono- or 
disubstituted by identical or different substituents from the group 
consisting of fluorine, chlorine, cyano, methyl, cyclopropyl, methoxy, 
methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, 
difluorochloromethoxy, 
T represents a single bond, represents oxygen, sulphur, --CH.sub.2 --O--, 
CH.sub.2 --S--, methylene, ethylene or propylene and 
R represents methyl, ethyl, methoxy, methylamino or hydroxylamino. 
The abovementioned general or preferred radical definitions apply both to 
the end products of the formula (I) and, correspondingly, to the starting 
materials or intermediates required in each case for preparation. 
These radical definitions can be combined with each other as desired, that 
is to say combinations between the ranges stated for preferred compounds 
are also possible. 
Examples of the compounds according to the invention are listed in Table 1 
with reference to the general formula Ia: 
TABLE 1 
__________________________________________________________________________ 
##STR14## 
Z G Ar.sup.1 
E R 
__________________________________________________________________________ 
##STR15## OCH.sub.2 
##STR16## 
##STR17## 
OCH.sub.3 
##STR18## OCH.sub.2 
##STR19## 
##STR20## 
OCH.sub.3 
##STR21## OCH.sub.2 
##STR22## 
##STR23## 
NHCH.sub.3 
##STR24## OCH.sub.2 
##STR25## 
##STR26## 
OCH.sub.3 
##STR27## OCH.sub.2 
##STR28## 
##STR29## 
OCH.sub.3 
##STR30## OCH.sub.2 
##STR31## 
##STR32## 
NHCH.sub.3 
##STR33## 
##STR34## 
##STR35## 
##STR36## 
OCH.sub.3 
##STR37## 
##STR38## 
##STR39## 
##STR40## 
OCH.sub.3 
##STR41## 
##STR42## 
##STR43## 
##STR44## 
NHCH.sub.3 
##STR45## 
##STR46## 
##STR47## 
##STR48## 
OCH.sub.3 
##STR49## 
##STR50## 
##STR51## 
##STR52## 
OCH.sub.3 
##STR53## 
##STR54## 
##STR55## 
##STR56## 
OCH.sub.3 
##STR57## 
##STR58## 
##STR59## 
##STR60## 
OCH.sub.3 
##STR61## 
##STR62## 
##STR63## 
##STR64## 
OCH.sub.3 
__________________________________________________________________________ 
The hydroxyl compounds required as starting materials to carry out the 
processes a) and b) according to the invention are defined in a general 
way by the formula (II). In this formula (II), A and Ar.sup.2 each 
preferably or in particular have those meanings already given in 
connection with the description of the compounds of the formula (I) 
according to the invention as preferred or as particularly preferred for A 
and Ar.sup.2. 
The hydroxyl compounds of the formula (II) are known and/or can be prepared 
by known processes (cf. JP-A 02001484). 
The halogen compounds further required as starting materials to carry out 
the process a) according to the invention are defined in a general way by 
the formula (III). In this formula (III), Ar.sup.1, Ar.sup.3, E, Q and R 
each preferably or in particular have those meanings already given in 
connection with the description of the compounds of the formula (I) 
according to the invention as preferred or as particularly preferred for 
Ar.sup.1, Ar.sup.3, E, Q and R. X represents halogen, preferably chlorine 
or fluorine. 
The halogen compounds of the formula (III) are known and/or can be prepared 
by known processes (cf. EP-A 382375). 
The halogen compounds further required as starting materials to carry out 
the process b) according to the invention are defined in a general way by 
the formula (IV). In this formula (IV), Ar.sup.1, E and R each preferably 
or in particular have those meanings already given in connection with the 
description of the compounds of the formula (I) according to the invention 
as preferred or as particularly preferred for Ar.sup.1, E and R. X 
represents halogen, preferably chlorine or bromine. 
The halogen compounds of the formula (IV) are known and/or can be prepared 
by known processes (cf. EP-A 226917 and EP-A 254426). 
The esters required as starting materials to carry out the process c) 
according to the invention are defined in a general way by the formula 
(I-1). In this formula (I-1), A, Ar.sup.1, Ar.sup.2, E and G each 
preferably or in particular have those meanings already given in 
connection with the description of the compounds of the formula (I) 
according to the invention as preferred or as particularly preferred for 
A, Ar.sup.1, Ar.sup.2, E and G. A.sup.1 represents alkyl, preferably 
methyl. The compounds of the formula (I-1) are compounds according to the 
invention and can be obtained by the processes (a) and (b) according to 
the invention. 
The amines further required as starting materials to carry out the process 
(c) according to the invention are defined in a general way by the formula 
(V). In the formula (V), A.sup.2 an A.sup.3 independently of one another 
each represent hydrogen, respectively optionally substituted alkyl, alkoxy 
or hydroxyl, A.sup.2 preferably represents hydrogen, A.sup.3 preferably 
represents methyl or hydroxyl. The amines of the formula (V) or their acid 
addition complexes are known reagents in organic chemistry. 
The processes a), b) and c) according to the invention are, if appropriate, 
carried out in the presence of a diluent. Suitable diluents are all inert 
organic solvents. These are preferably aliphatic, alicyclic or aromatic 
hydrocarbons, such as, for example petroleum ether, hexane, heptane, 
cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; 
halogenated hydrocarbons, such as, for example, chlorobenzene, 
dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 
dichloroethane or trichloroethane; ethers, such as diethyl ether, 
diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxan, 
tetrahydrofuran, 1,2- dimethoxyethane, 1,2-diethoxyethane or anisole; 
ketones, such as acetone, butanone, methyl isobutyl ketone or 
cyclohexanone; nitrites, 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; esters, such as methyl acetate, or ethyl 
acetate; sulphoxides, such as dimethyl sulphoxide or sulphones, such as 
sulpholane. The process c) according to the invention can, if appropriate, 
also be carried out in alcohols, such as methanol, ethanol, n- or 
i-propanol, n-, i-, sec- or t-butanol, ethanediol, propane-1,2-diol, 
ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, 
diethylene glycol monoethyl ether, their mixtures with water or in pure 
water. 
The processes a), b) and c) according to the invention are, if appropriate, 
carried out in the presence of a suitable acid acceptor. Suitable acid 
acceptors are all customary inorganic or organic bases. These are, for 
example alkaline earth metal or alkali metal hydrides, hydroxides, amides, 
alkoxides, acetates, carbonates or bicarbonates, such as, for example, 
sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium 
tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, 
sodium acetate, potassium acetate, calcium acetate, ammonium acetate, 
sodium carbonate, potassium carbonate, potassium bicarbonate, sodium 
bicarbonate or ammonium carbonate, and also tertiary amines, such as 
trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, 
N,N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, 
N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazaobicyclononene 
(DBN) or diazabicycloundecene (DBU). 
When carrying out the process according to the invention, the reaction 
temperatures may be varied over a relatively wide range. In general, 
temperatures between -20.degree. C. and +200.degree. C. are employed. 
Processes a) and b) are preferably carried out at temperatures between 
20.degree. C. and 150.degree. C., process c) is preferably carried out at 
temperatures of 0.degree.-80.degree. C. 
The processes a) and b) according to the invention for preparing the 
compounds of the formula (I) according to the invention are carried out by 
employing generally 0.5 to 5 mol, preferably 0.8 to 1.5 mol, of halogen 
compound of the formula (III) or (IV) per mole of hydroxyl derivative of 
the formula (II). 
The process c) according to the invention for preparing the compounds of 
the formula (I) according to the invention is carried out by employing 
generally 1 to 100 mol, preferably 1 to 20 mol, of amine of formula (V) 
per mole of ester of the formula (I-1). 
The reaction is carried out and the reaction products are worked up and 
isolated according to known processes (cf. also the Preparation Examples). 
The active compounds according to the invention have a potent microbicidal 
activity and are employed in practice for controlling undesirable 
microorganisms. The active compounds are suitable for use as crop 
protection agents, in particular as fungicides. 
Fungicides are employed in crop protection for controlling 
Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, 
Ascomycetes, Basidiomycetes and Deuteromycetes. 
Some pathogens causing fungal diseases which come under the generic names 
listed above may be mentioned as examples, but not by way of limitation: 
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 Pseudoperonospora cubense; 
Plasmopara species, such as, for example, Plasmopara viticola; 
Peronospora species, such as, for example, Peronospora pisi or Peronospora 
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 Pyrenophora 
graminea (conidial form: Drechslera, synonym: Helminthosporium); 
Cochliobolus species, such as, for example, Cochliobolus sativus (conidiae 
form: Drechslera, synonym: Helminthosporium); 
Uromyces species, such as, for example, Uromyces appendiculatus; 
Puccinia species, such as, for example, Puccinia recondita; 
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 brassicae; 
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 according to the invention can be employed 
particularly successfully for controlling diseases in viticulture, 
fruit-growing and horticulture, such as, for example, against Plasmopara 
species and Podosphaera species. 
The active compounds according to the invention are also employed very 
successfully for controlling cereal diseases, such as, for example, 
against Septoria species, Pyricularia species, Pyrenophora species and 
Cochliobolus species. Furthermore, the active compounds according to the 
invention have an excellent in vitro activity. Depending on their 
particular physical and/or chemical properties, the active compounds can 
be converted to the customary formulations, such as solutions, emulsions, 
suspensions, powders, foams, pastes, granules, aerosols and 
microencapsulations in polymeric substances and in coating compositions 
for seeds, and ULV cold and warm fogging formulations. 
These formulations are produced in a known manner, for example by mixing 
the active compounds with extenders, that is, liquid solvents, liquefied 
gases under pressure, and/or solid carriers, optionally with the use of 
surfactants, 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 chlorobenzenes, chloroethylenes or methylene 
chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for 
example petroleum 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 halogenated hydrocarbons, or else 
butane, propane, nitrogen and carbon dioxide; suitable solid carriers are: 
for example, ground natural minerals such as kaolins, clays, talc, chalk, 
quartz, attapulgite, montmorillonite or diatomaceous earth, and ground 
synthetic minerals such as finely divided 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 can be used as such or, in 
their formulations, also as a mixture with known fungicides, bactericides, 
acaricides, nematicides or insecticides in order thus, for example, to 
widen the spectrum of action or to prevent development of resistance. 
In many cases, synergistic effects are achieved. 
Examples of co-components in 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-thiazole-5-carboxanilide; 
2,6-dichloro-N-(4-trifluoromethylbenzyl)-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)-methoximinoalpha-(o-tolyloxy)-o-tolyl!acetate; 2-phenylphenol 
(OPP), aldimorph, ampropylfos, anilazine, azaconazole, 
benalaxyl, benodanil, benomyl, binapacryl, biphenyl, bitertanol, 
blasticidin-S, bromuconazole, bupirimate, buthiobate, 
calcium polysulphide, captafol, captan, carbendazim, carboxin, 
quinomethionate, chloroneb, chloropicrin, chlorothalonil, chlozolinate, 
cufraneb, cymoxanil, cypro-conazole, cyprofuram, 
dichlorophen, diclobutrazol, diclofluanid, diclomezine, dicloran, 
diethofencarb,difenoconazole, dimethirimol, dimethomorph, diniconazole, 
dinocap, diphenylamine,dipyrithione, 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, pencycuron, 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, furancarboxylic acid, oxytetracycline, 
probenazole, streptomycin, tecloftalam, copper sulphate and other copper 
preparations. 
Insecticides/Acaricides/Nematicides: 
abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, 
alphamethrin, amitraz, avermectin, AZ 60541, azadirachtin, azinphos A, 
azinphos M, azocyclotin, 
Bacillus thuringiensis, bendiocarb, benfuracarb, bensultap, betacyluthrin, 
bifenthrin, BPMC, brofenprox, bromophos A, bufencarb, buprofezin, 
butocarboxin, butylpyridaben, 
cadusafos, carbaryl, carbofuran, carbophenothion, carbosulphan, cartap, CGA 
157419, CGA 184699, chloethocarb, chlorethoxyfos, chloretoxyfos, 
chlorfenvinphos, 
chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M, cis-resmethrin, 
clocythrin, clofentezine, cyanophos, cycloprothrin, cyfluthrin, 
cyhalothrin, cyhexatin, cypermethrin, cyromazine, 
deltamethrin, demeton M, demeton S, demeton-S-methyl, diafenthiuron, 
diazinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, 
diflubenzuron, dimethoate, dimethylvinphos, dioxathion, disulfoton, 
edifenphos, emarnectin, esfenvalerate, ethiofencarb, ethion, ethofenprox, 
ethoprophos, etofenprox, etrimphos, 
fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, 
fenothiocarb, fenoxycarb, fenpropathrin, fenpyrad, fenpyroximate, 
fenthion, fenvalerate, 
fipronil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, 
flufenprox, fluvalinate, fonophos, formothion, fosthiazate, fubfenprox, 
furathiocarb, 
HCH, heptenophos, hexaflumuron, hexythiazox, 
imidacloprid, iprobenfos, isazophos, isofenphos, isoprocarb, isoxathion, 
ivemectin, 
lamda-cyhalothrin, lufenuron, 
malathion, mecarbam, mervinphos, mesulfenfos, metaldehyde, methacrifos, 
methamidophos, methidathion, methiocarb, methomyl, metolcarb, milbemectin, 
monocrotophos, moxidectin, 
naled, NC 184, NI 25, nitenpyram, 
omethoate, oxamyl, oxydemethon M, oxydeprofos, 
parathion A, parathion M, pernethrin, phenthoate, phorate, phosalone, 
phosmet, 
phosphamdon, phoxim, pirimicarb, pirimiphos M, ,primiphos A, profenofos, 
profenophos, promecarb, propaphos, propoxur, prothiofos, prothiophos, 
prothoate, 
pymetrozin, pyrachlophos, pyraclofos, pyraclophos, pyradaphenthion, 
pyresmethrin, pyrethrum, pyridaben, pyrimidifen, pyriproxifen, 
quinalphos, 
RH 5992, 
salithion, sebufos, silafluofen, sulfotep, sulprofos, 
tebufenozid, tebufenpyrad, tebupirimphos, teflubenzuron, tefluthrin, 
temephos, terbam, terbufos, tetrachlorvinphos, thiafenox, thiodicarb, 
thiofanox, thiomethon, thionazin, thuringiensin, tralomethrin, 
triarathene, triazophos, triazuron, trichlorfon, triflumuron, 
trimethacarb, 
vamidothion, XMC, xylylcarb, YI 5301/5302, zetamethrin. 
It is also possible to admix other known active compounds, such as 
herbicides, or fertilizers and growth regulators. 
The active compounds can be used as such or in the form of their 
formulations or the use forms prepared therefrom, such as ready-to-use 
solutions, suspensions, wettable powders, pastes, soluble powders, dusts 
and granules. They are used in the customary manner, for example by 
wetting, spraying, atomizing, spreading, dusting, foaming, brushing on and 
the like. It is further 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 from 0.001 to 50 g, 
preferably 0.01 to 10 g, are generally required per kilogram of seed. 
In the treatment of the soil, active compound concentrations of from 
0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight, are 
required at the site of action.

PREATION EXAMPLES 
Example 1 
##STR65## 
2.85 g (0.01 mol) of methyl 2-(2-bromomethylphenyl)-3-methoxyacrylate, 1.8 
g (0.01 mol) of 3-(2-hydroxyphenyl)-5,6-dihydro-1,4,2-dioxazine and 1.3 g 
of potassium tert-butoxide in 50 ml of tetrahydrofuran are heated under 
reflux for 4 hours. The solution is then evaporated to dryness, taken up 
in 50 ml of water and extracted with ethyl acetate. The organic phase is 
dried and concentrated under reduced pressure. Finally, the residue is 
purified by column chromatography over silica gel using 
dichloromethane/ethyl acetate (10:1). 
2.9 g (76.3%) of the target compound are obtained as a pale yellow oil. 
.sup.1 H NMR (CDCl.sub.3 /TMS).delta.(ppm): 3.71 (s,3 H), 3.82 (s,3 H), 
4.20 (m,2 H), 4.47 (m,2 H), 5.04 (s,2 H), 6.75-7.5 (m,8 H), 7.61 (s,1 H). 
Example 2 
##STR66## 
8.6 g (0.03 mol) of methyl 2-(2-bromomethylphenyl)-2-methoximinoacetate, 
5.4 g(0.03 mol) of 3-(2-hydroxyphenyl)-5,6-dihydro-1,4,2-dioxazine and 1 g 
(0.033 mol) of sodium hydride (80%) in 50 ml of tetrahydrofuran are heated 
under reflux for 4 hours. The solution is then evaporated to dryness, 
taken up in 50 ml of water and extracted with ethyl acetate. The organic 
phase is dried and concentrated under reduced pressure. Finally, the 
residue is purified by column chromatography over silica gel using 
dichloromethane/ethyl acetate (10:1). 
3.5 g (31%) of the target compound are obtained as a white solid. 
Melting point: 179.degree. C. 
Example 3 
##STR67## 
At room temperature, 0.7 g (0.022 mol) of 80% sodium hydride are added with 
stirring to a mixture of 6.4 g (0.02 mol) of methyl 
E-3-methoxy-2-2-(6-chloro-4-pyrimidinyl-oxy)-phenyl!acrylate (cf. for 
example EP 382375) and 3.6 g (0.02 mol) 
of3-(3-hydroxyphenyl)-5,6-dihydro-1,4,2-dioxazine in 50 ml of absolute 
N,N-dimethylformamide, and the mixture is stirred for a further 16 hours 
at room temperature. For work-up, the mixture is poured into a 
half-concentrated ammonium chloride solution and extracted twice with 100 
ml of methyl t-butyl ether each time. The combined organic phases are 
dried and concentrated under reduced pressure, and the residue is purified 
by column chromatography over silica gel using (dichloromethane/ethyl 
acetate 10: 1). 
6.9 g (74.5% of theory) of methyl 
E-3-methoxy-2-{2-6-(3-&lt;5,6-dihydro-1,4,2-dioxazinyl&gt;-phenoxy)-4-pyrimidin 
yloxy!-phenyl}-acrylate are obtained as an oil. 
.sup.1 H NMR (CDCl.sub.3 /TMS).delta.(ppm): 3.61 (s,3 H), 3.75 (s,3 H), 
4.20 (m,2 H), 4.51 (m,2 H), 
Example 4 
##STR68## 
MethylE-3-methoxy-2-2-(6-chloro-4-pyrimidinyloxy)-phenyl!acrylate6.4 
g(0.02 mol) of methyl 
E-3-methoxy-2-2-(5-fluoro-6-chloro-4-pyrimidinyloxy)-phenyl!acrylate, 3.6 
g (0.02 mol) of 3-(3-hydroxyphenyl)-5,6-dihydro-1,4,2-dioxazine and 2.7 g 
(0.024 mol) of potassium t-butoxide in 50 ml of tetrahydrofuran are heated 
under reflux for 4 hours. The solution is then evaporated to dryness, 
taken up in 50 ml of water and extracted with ethyl acetate. The organic 
phase is dried and concentrated under reduced pressure. Finally, the 
residue is purified by column chromatography over silica gel using 
dichloromethane/ethyl acetate (10:1). 1.5 g (15.6%) of the target compound 
are obtained as a pale yellow oil. 
.sup.1 H NMR (CDCl.sub.3 /TMS).delta.(ppm): 3.63 (s,3 H), 3.79 (s,3 H), 
4.11 (m,2H), 4.39 (m,2 H), 
Similarly to Examples 1 to 4, and according to the general description of 
the preparation processes according to the invention, the compounds listed 
in Table 2 below, for example, can also be prepared: 
TABLE 2 
__________________________________________________________________________ 
##STR69## 
Ex. No. 
Z G Ar.sup.1 
E R physical constants 
__________________________________________________________________________ 
##STR70## OCH.sub.2 
##STR71## 
##STR72## 
OCH.sub.3 
.sup.1 H NMR (CDCl.sub.3 
/TMS): 3.69(s, 3H), 3.81(s, 
3H), 4.18(m, 2H), 4.49(m, 
2H), 4.96(s, 2H), 
6 
##STR73## OCH.sub.2 
##STR74## 
##STR75## 
OCH.sub.3 
.sup.1 H NMR (CDCl.sub.3 
/TMS): 3.69(s, 3H), 3.81(s, 
3H), 4.16(m, 2H), 4.48(m, 
2H), 4.98(s, 2H), 
7 
##STR76## 
##STR77## 
##STR78## 
##STR79## 
OCH.sub.3 
8 
##STR80## OCH.sub.2 
##STR81## 
##STR82## 
OCH.sub.3 
Mp.: 119.degree. C. 
9 
##STR83## 
##STR84## 
##STR85## 
##STR86## 
OCH.sub.3 
1H NMR: 3.64(s, 3H), 
3.79(s, 3H), 4.21(m, 2H), 
4.53(m, 2H), 
10 
##STR87## 
##STR88## 
##STR89## 
##STR90## 
OCH.sub.3 
1H NMR: 3.63(s, 3H), 
3.79(s, 3H), 4.11(m, 2H), 
4.39(m, 2H) 
__________________________________________________________________________ 
Example A 
Plasmopara test (vines)/protective 
Solvent: 4.7 parts by weight of acetone 
Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amounts of solvent and 
emulsifier, and -the concentrate is diluted with water to the desired 
concentration. 
To test for protective activity, young plants are sprayed with the 
preparation of active compound. After the spray coating has dried on, the 
plants are inoculated with an aqueous spore suspension of Plasmopara 
viticola and they then remain for 1 day in a humid chamber at 20.degree. 
to 22.degree. C. and 100% of relative atmospheric humidity. The plants are 
then kept for 5 days in a greenhouse at 21.degree. C. and about 90% of 
atmospheric humidity. The plants are then moistened and kept for 1 day in 
a humid chamber. 
Evaluation is carried out 6 days after the inoculation. 
In this test, an efficacy of up to 98% is shown, for example, by the 
following compounds (3), (5) and (8) at an active compound concentration 
of 100 ppm. 
Example B 
Podosphaera test (apple)/protective 
Solvent: 4.7 parts by weight of acetone 
Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether 
To produce a suitable preparation of active compound, 1 part by weight of 
active compound is mixed with the stated amounts of solvent and 
emulsifier, and the concentrate is diluted with water to the desired 
concentration. 
To test for protective activity, young plants are sprayed with the 
preparation of active compound to run-off point. After the spray coating 
has dried on, the plants are inoculated by dusting with conidia of the 
causative organism of apple mildew (Podosphaera leucotricha). 
The plants are then placed in a greenhouse at 23.degree. C. and relative 
atmospheric humidity of about 70%. 
Evaluation is carried out 10 days after the inoculation. 
In this test, an efficacy of up to 100% is shown, for example, by the 
following compounds of Preparation Examples (2), (3), (5) and (7) at an 
active compound concentration of 100 ppm.