U.S. patent application number 09/879902 was filed with the patent office on 2002-02-14 for salicylohydrazide derivatives, processes and intermediates for their preparation, compositions comprising them, and their use.
Invention is credited to Ammermann, Eberhard, Blasco, Jordi Tormo i, Cullmann, Oliver, Gewehr, Markus, Grammenos, Wassilios, Grote, Thomas, Gypser, Andreas, Lorenz, Gisela, Muller, Bernd, Rheinheimer, Joachim, Rose, Ingo, Sauter, Hubert, Schafer, Peter, Stierl, Reinhard, Strathmann, Siegfried.
Application Number | 20020019374 09/879902 |
Document ID | / |
Family ID | 7645496 |
Filed Date | 2002-02-14 |
United States Patent
Application |
20020019374 |
Kind Code |
A1 |
Gypser, Andreas ; et
al. |
February 14, 2002 |
Salicylohydrazide derivatives, processes and intermediates for
their preparation, compositions comprising them, and their use
Abstract
Salicylohydrazide derivatives of the formula I 1 in which the
index and the substituents have the following meanings: X is
halogen, NO.sub.2, cyano, alkyl or alkoxy; m is 0, 1, 2 or 3, it
being possible for the substituents X to differ from each other if
n is greater than 1; R.sup.1 is NO.sub.2, NH.sub.2 or NH--CO--A; A
is hydrogen, alkyl, alkoxy, NH.sub.2, NHCH.sub.3 or
N(CH.sub.3).sub.2; R.sup.2 is hydrogen, cyano, alkyl, alkenyl,
alkynyl, haloalkyl, alkoxy or alkylthio; it being possible for the
hydrocarbon radicals to be unsubstituted or substituted, R.sup.3 is
phenyl, naphthyl, cycloalkyl, 5-membered or 6-membered hetaryl or
5-membered or 6-membered heterocyclyl containing one to three N
atoms and/or one O or S atom or one or two O and/or S atoms, the
ring systems being unsubstituted or substituted; the preparation of
these compounds, compositions comprising them, and their use for
controlling harmful fungi.
Inventors: |
Gypser, Andreas; (Mannheim,
DE) ; Grote, Thomas; (Wachenheim, DE) ;
Rheinheimer, Joachim; (Ludwigshafen, DE) ; Rose,
Ingo; (Mannheim, DE) ; Schafer, Peter;
(Ottersheim, DE) ; Cullmann, Oliver; (Heppenheim,
DE) ; Gewehr, Markus; (Kastellaun, DE) ;
Grammenos, Wassilios; (Ludwigshafen, DE) ; Blasco,
Jordi Tormo i; (Limburgerhof, DE) ; Muller,
Bernd; (Frankenthal, DE) ; Sauter, Hubert;
(Mannheim, DE) ; Ammermann, Eberhard; (Heppenheim,
DE) ; Strathmann, Siegfried; (Limburgerhof, DE)
; Lorenz, Gisela; (Hambach, DE) ; Stierl,
Reinhard; (Mutterstadt, DE) |
Correspondence
Address: |
Herbert B. Keil
KEIL & WEINKAUF
1101 Connecticut Ave., N.W.
Washington
DC
20036
US
|
Family ID: |
7645496 |
Appl. No.: |
09/879902 |
Filed: |
June 14, 2001 |
Current U.S.
Class: |
514/159 ;
544/162; 544/163; 546/229; 548/567; 558/422; 560/27; 560/29;
564/150 |
Current CPC
Class: |
C07C 255/66 20130101;
C07C 251/86 20130101; A01N 37/46 20130101; A01N 37/40 20130101;
A01N 47/30 20130101; A01N 47/20 20130101 |
Class at
Publication: |
514/159 ;
558/422; 564/150; 560/27; 560/29; 548/567; 546/229; 544/162;
544/163 |
International
Class: |
A01N 037/36; C07C
235/44 |
Foreign Application Data
Date |
Code |
Application Number |
Jun 16, 2000 |
DE |
10028978.9 |
Claims
We claim:
1. A salicylohydrazide derivative of the formula I 23in which the
index and the substituents have the following meanings: X is
halogen, NO.sub.2, cyano, C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy; m is 0, 1, 2 or 3, it being possible for
the substituents X to differ from each other if n is greater than
1; R.sup.1 is NO.sub.2, NH.sub.2 or NH--CO--A; A is hydrogen,
C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, NH.sub.2, NHCH.sub.3
or N(CH.sub.3).sub.2; R.sup.2 is hydrogen, cyano,
C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkoxy or C.sub.1-C.sub.6-alkylthio; it being
possible for the hydrocarbon radicals to be unsubstituted or to be
partially or fully halogenated or to have 1 to 3 groups R.sup.a
R.sup.a is halogen, cyano, nitro, hydroxyl, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylca- rbonyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylamino,
di-C.sub.1-C.sub.6-alkylamino, C.sub.2-C.sub.6-alkenyl,
C.sub.3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-alkynyloxy or
C.sub.1-C.sub.4-alkylenedioxy which can be halogenated, R.sup.3 is
phenyl, naphthyl, C.sub.3-C.sub.10-cycloalkyl, 5-membered or
6-membered hetaryl or 5-membered or 6-membered heterocyclyl
containing one to three n atoms and/or one O or s atom or one or
two O and/or s atoms, the ring systems being unsubstituted or
substituted by one to three radicals R.sup.b: R.sup.b is cyano,
nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, hydroxyl,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-alkylsulfoxyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkyloxycarbonyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino, di-C.sub.1-C.sub.6-alkylamino,
C.sub.1-C.sub.6-alkylaminocarbonyl,
di-C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.1-C.sub.6-alkylaminothiocarb- onyl,
di-C.sub.1-C.sub.6-alkylaminothiocarbonyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5-
or 6-membered heterocyclyl, 5- or 6-membered hetaryl, 5- or
6-membered hetaryloxy, C(.dbd.NOR.sup..alpha.)--OR.sup..beta. or
OC(R.sup..alpha.).sub.2--C(R.sup..beta.).dbd.NOR.sup..beta., the
cyclic radicals, in turn, being unsubstituted or substituted by one
to three radicals R.sup.c: R.sup.c is cyano, nitro, halogen,
hydroxyl, amino, aminocarbonyl, aminothiocarbonyl,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-alkylsulfoxyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkoxycarbonyl,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylamino,
di-C.sub.1-C.sub.6-alkylamino, C.sub.1-C.sub.6-alkylaminocarbonyl,
di-C.sub.1-C.sub.6-alkylaminocarbonyl- ,
C.sub.1-C.sub.6-alkylaminothiocarbonyl,
di-C.sub.1-C.sub.6-alkylaminothi- ocarbonyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkenyloxy,
C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkenyl, phenyl,
phenoxy, phenylthio, benzyl, benzyloxy, 5- or 6-membered
heterocyclyl, 5- or 6-membered hetaryl, 5- or 6-membered hetaryloxy
or C(.dbd.NOR.sup..alpha.)--OR.sup..beta., R.sup..alpha.,
R.sup..beta. are hydrogen or C.sub.1-C.sub.6-alkyl.
2. A compound of the formula I as claimed in claim 1 where R.sup.1
is NH--CO--A.
3. A compound of the formula I as claimed in claim 1 where m is
zero.
4. A compound of the formula I as claimed in claim 1 where m is 1
and X is in the 4-position.
5. A compound of the formula I as claimed in claim 1 where A is
hydrogen, C.sub.1-C.sub.4-alkoxy, NHCH.sub.3 or N(CH.sub.3).sub.2:
R.sup.2 is CN or C.sub.1-C.sub.6-alkyl; R.sup.3 is phenyl or
5-membered or 6-membered hetaryl, the ring systems being
unsubstituted or substituted by one to three radicals R.sup.b.
6. A process for the preparation of compounds of the formula I as
claimed in claim 1 by reacting hydrazides of the formula II 24with
carbonyl compounds of the formula III 25to give compounds of the
formula I where R.sup.1 is NO.sub.2, 26and, to prepare compounds I
where R.sup.1 is NH.sub.2 or NH--CO--A, hydrogenating IA to give
aminophenol compounds of the formula IB, 27and, to prepare
compounds I where R.sup.1 is NH--CO--H, formylation of IB to give
compounds of the formula I.1 28or, to prepare compounds I where
R.sup.1 is NH--CO--NH.sub.2, reacting Is with alkali metal
isocyanates or alkaline earth metal isocyanates to give compounds
of the formula I.2, 29or, to prepare compounds I where R.sup.1 is
NH--CO--NHCH.sub.3, reacting IB with methyl isocyanate to give
compounds of the formula I.3, 30or, to prepare compounds I where
R.sup.1 is NH--CO--N(CH.sub.3).sub.2, reacting IB with phosgene and
dimethylamine to give compounds of the formula I.4, 31or, to
prepare compounds I in which R.sup.1 is NH--CO--OCH.sub.3, reacting
In with carbon monoxide and methanol with transition-metal
catalysis to give compounds of the formula I.5 32
7. The use of the compounds of the formulae IA and IB as
intermediates.
8. A composition which is suitable for controlling phytopathogenic
harmful fungi, comprising a solid or liquid carrier and a compound
of the formula I as claimed in claim 1.
9. A method of controlling phytopathogenic harmful fungi, which
comprises treating the fungi, or the materials, plants, the soil or
seed to be protected from fungal attack, with an effective amount
of a compound of the formula I as claimed in claim 1.
Description
[0001] Salicylohydrazide derivatives, processes and intermediates
for their preparation, compositions comprising them, and their
use
[0002] The present invention relates to salicylohydrazide
derivatives of the formula I 2
[0003] in which the index and the substituents have the following
meanings:
[0004] X is halogen, NO.sub.2, cyano, C.sub.1-C.sub.4-alkyl or
C.sub.1-C.sub.4-alkoxy;
[0005] m is 0, 1, 2 or 3, it being possible for the substituents X
to differ from each other if n is greater than 1;
[0006] R.sup.1 is NO.sub.2, NH.sub.2 or NH--CO--A;
[0007] A is hydrogen, C.sub.1-C.sub.4-alkyl,
C.sub.1-C.sub.4-alkoxy, NH.sub.2, NHCH.sub.3 or
N(CH.sub.3).sub.2;
[0008] R.sup.2 is hydrogen, cyano, C.sub.1-C.sub.6-alkyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl,
C.sub.1-C.sub.6-haloalk- yl, C.sub.1-C.sub.6-alkoxy or
C.sub.1-C.sub.6-alkylthio;
[0009] it being possible for the hydrocarbon radicals to be
unsubstituted or to be partially or fully halogenated or to have 1
to 3 groups R.sup.a
[0010] R.sup.a is halogen, cyano, nitro, hydroxyl,
C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl,
C.sub.1-C.sub.6-alkylcarbonyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkoxycarbonyl, C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino,
[0011] di-C.sub.1-C.sub.6-alkylamino, C.sub.2-C.sub.6-alkenyl,
C3-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-alkynyloxy or
C.sub.1-C.sub.4-alkylenedioxy which can be halogenated,
[0012] R.sup.3 is phenyl, naphthyl, C.sub.3-C.sub.10-cycloalkyl,
5-membered or 6-membered hetaryl or 5-membered or 6-membered
heterocyclyl containing one to three N atoms and/or one O or S atom
or one or two O and/or S atoms, the ring systems being
unsubstituted or substituted by one to three radicals R.sup.b:
[0013] R.sup.b is cyano, nitro, amino, aminocarbonyl,
aminothiocarbonyl, halogen, hydroxyl, C.sub.1-C.sup.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl,
C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-alkylsulfoxyl,
C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy,
C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkyloxycarbonyl,
C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylamino,
di-C.sub.1-C.sub.6-alkylamino, C.sub.1-C.sub.6-alkylaminocarbonyl,
di-C.sub.1-C.sub.6-alkylaminocarbonyl- ,
C.sub.1-C.sub.6-alkylaminothiocarbonyl,
di-C.sub.1-C.sub.6-alkylaminothi- ocarbonyl,
C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkenyloxy, phenyl,
phenoxy, benzyl, benzyloxy, 5- or 6-membered heterocyclyl, 5- or
6-membered hetaryl, 5- or 6-membered hetaryloxy,
C(.dbd.NOR.sup..alpha.)-- -OR.sup..beta. or
OC(R.sup..alpha.).sub.2--C (R.sup..beta.).dbd.NOR.sup..b- eta.,
[0014] the cyclic radicals, in turn, being unsubstituted or
substituted by one to three radicals R.sup.c:
[0015] R.sup.c is cyano, nitro, halogen, hydroxyl, amino,
aminocarbonyl, aminothiocarbonyl, C.sub.1-C.sub.6-alkyl,
C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylsulfonyl,
C.sub.1-C.sub.6-alkylsulfoxyl, C.sub.3-C.sub.6-cycloalkyl,
C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy,
C.sub.1-C.sub.6-alkoxycarbonyl. C.sub.1-C.sub.6-alkylthio,
C.sub.1-C.sub.6-alkylamino, di-C-C.sub.6-alkylamino,
C.sub.1-C.sub.6-alkylaminocarbonyl,
di-C.sub.1-C.sub.6-alkylaminocarbonyl,
C.sub.1-C.sub.6-alkylaminothiocarb- onyl,
di-C.sub.1-C.sub.6-alkylaminothiocarbonyl, C.sub.2-C.sub.6-alkenyl,
C.sub.2-C.sub.6-alkenyloxy, C.sub.3-C.sub.6-cycloalkyl,
C.sub.3-C.sub.6-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl,
benzyloxy, 5- or 6-membered heterocyclyl, 5- or 6-membered hetaryl,
5- or 6-membered hetaryloxy or
C(.dbd.NOR.sup..alpha.)--OR.sup..beta.;
[0016] R.sup..alpha., R.sup..beta. are hydrogen or
C.sub.1-C.sub.6-alkyl.
[0017] Furthermore, the invention relates to processes for the
preparation of these compounds, to compositions comprising them,
and to their use for controlling harmful fungi.
[0018] WO-A 97/08135, DE-A 197 10 609 and WO-A 99/27783 disclose
acylaminosalicylamides for controlling harmful fungi.
[0019] However, their action is unsatisfactory in many cases.
Compounds with an improved action are an object of the present
invention.
[0020] We have found that this object is achieved by the compounds
defined at the outset. Moreover, there have been found processes
for their preparation, compositions comprising them, and methods of
controlling harmful fungi using the compounds I.
[0021] The compounds of the formula I differ from those known from
the prior art by the hydrazide group.
[0022] Compared with the known compounds, the compounds of the
formula I exhibit an increased efficacy against harmful fungi.
[0023] For example, compounds of the formula I can be synthesized
starting from hydrazides of the formula II by subjecting hydrazides
and carbonyl compounds of the formula III to a condensation
reaction. The compounds of the formula IA are also used as
intermediates for the preparation of further compounds I. 3
[0024] This reaction is usually carried out at temperatures from
20.degree. C. to 100.degree. C., preferably 20.degree. C. to
50.degree. C., in an inert organic solvent in the presence of an
acid [cf. Indian J. Chem. B, (1983), Vol. 24, p. 979].
[0025] Suitable solvents are aromatic hydrocarbons such as toluene,
o-, m- and p-xylene, halogenated hydrocarbons such as methylene
chloride, chloroform and chlorobenzene, ethers such as diethyl
ether, diisopropyl ether, tert-butyl methylether, dioxane and
tetrahydrofuran, nitriles such as acetonitrile and propionitrile,
alcohols such as methanol, ethanol, n-propanol, isopropanol and
n-butanol, and also dimethyl sulfoxide, dimethylformamide and
dimethylacetamide, especially preferably alcohols such as methanol,
ethanol, n-propanol, isopropanol and n-butanol. Mixtures of these
solvents may also be used.
[0026] Acid and acidic catalysts which are used are inorganic acids
such as hydrofluoric acid, (aqueous) hydrochloric acid, tetrabromic
acid, sulfuric acid and perchloric acid, Lewis acids such as boron
trifluoride, aluminum trichloride, iron(III) chloride, tin(IV)
chloride, titanium(IV) chloride and zinc(II) chloride, and organic
acids such as formic acid, acetic acid, propionic acid, oxalic
acid, citric acid, trifluoroacetic acid, p-toluenesulfonic acid,
benzenesulfonic acid and camphorsulfonic acid.
[0027] In general, the acids are employed in catalytic amounts, but
they may also be used in equimolar amounts, in an excess or, if
appropriate, as solvent.
[0028] In general, the starting materials are reacted with each
other in equimolar amounts. It may be advantageous for the yield to
employ III in an excess based on II.
[0029] The starting materials II and III required for the
preparation of compounds I are commercially available, known from
the literature [ZA 70/00662; Labdev, (1973), part A, Vol. 11A(1-2),
p. 35] or can be prepared in accordance with the literature
cited.
[0030] To prepare compounds I where R.sup.1 is NH.sub.2 or
NH--CO--A, hydrazides of the formula IA are reduced to aminophenol
compounds of the formula IB. 4
[0031] The nitro group of IA can be reduced under generally
customary conditions by reduction with iron, tin or zinc in the
presence of an acid or by enzyme-catalyzed reduction [cf.
Houben-Weyl, Vol. IV/1c, 4th Ed., p. 506, Thieme Verlag Stuttgart
and New York (1980); ibid. Vol. IV/1d, 4th Ed., p. 473 (1981);
Heterocycles (1990), Vol. 31. p. 2201].
[0032] The reaction with hydrogen is preferably carried out by
catalytic hydrogenation at -20.degree. C. and +180.degree. C.,
preferably between -5 and +40.degree. C. The minimum temperature is
only determined by the freezing point of the solvent used.
Normally, the hydrogenation is carried out at a hydrogen pressure
between atmospheric pressure and at an superatmospheric pressure of
30 bar. Normally, the hydrogen is passed in under atmospheric or
slight superatmospheric pressure [cf. WO-A 97/08135].
[0033] Catalysts which are employed for the catalytic hydrogenation
are commercially available catalysts which comprise, for example,
platinum, platinum oxide or palladium on a support, or else Raney
nickel or Raney cobalt.
[0034] The use of platinum catalysts or palladium catalysts is
preferred. The platinum or palladium content of the catalyst is not
critical and can be varied within wide limits. A content of from
0.1 to 15% by weight, preferably from 0.5 to 10% by weight, based
on the support material, is expedient. The amount of the platinum
or palladium employed is between 0.001 and 10% by weight,
preferably between 0.01 and 0.1% by weight, based on the nitro
compound. In the preferred embodiment, carbon is used as support
material. Other non-amphoteric supports such as graphite,
BaSO.sub.4 or SiC, are also suitable.
[0035] Suitable diluents are esters such as ethyl acetate, alcohols
such as methanol, ethanol, n-propanol, n-, i-, sec- or
tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,
methoxyethanol, ethers such as diethylene glycol monomethyl ether,
diethylene glycol monomethyl ether, water, aqueous salt solutions
such as, for example, ammonium chloride solution, acids, such as,
for example, hydrochloric acid or acetic acid; methanol, ethanol
and water are especially preferred. Mixtures of these diluents may
also be used.
[0036] In general, the acids are employed in catalytic amounts, but
they may also be used in equimolar amounts, in an excess or, if
appropriate, as solvent.
[0037] To prepare compounds I in which R.sup.1 is NH--CO--A,
aminophenols of the formula IB are used as intermediates.
[0038] The aminophenols of the formula IB are preferably formylated
with formic acid. This gives directly the compounds of the formula
I in which R.sup.1 is NH--CO--H, which correspond to the formula
I.1 5
[0039] This reaction is usually carried out at temperatures of from
20.degree. C. to 100.degree. C., preferably from 20.degree. C. to
80.degree. C., in an inert organic solvent in the presence of an
acid.
[0040] Suitable solvents are aliphatic hydrocarbons such as
pentane, hexane, cyclohexane and petroleum ether, aromatic
hydrocarbons such as toluene, o-, m- and p-xylene, halogenated
hydrocarbons such as methylene chloride, chloroform and
chlorobenzene, ethers such as diethyl ether, diisopropyl ether,
tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran.
Mixtures of the solvents stated may also be used.
[0041] Acids and acidic catalysts which are used are inorganic
acids such as hydrofluoric acid, aqueous hydrochloric acid,
hydrobromic acid, sulfuric acid and perchloric acid, Lewis acids
such as boron trifluoride, aluminum trichloride, iron(III)
chloride, tin(IV) chloride, titanium(IV) chloride and zinc(II)
chloride, and organic acids such as formic acid, acetic acid,
propionic acid, oxalic acid, citric acid, trifluoroacetic acid,
p-toluenesulfonic acid, benzenesulfonic acid and camphorsulfonic
acid.
[0042] In general, the acids are employed in catalytic amounts, but
they may also be used in equimolar amounts, in an excess or, if
appropriate, as solvent.
[0043] In general, the starting materials are reacted with each
other in equimolar amounts. It may be advantageous for the yield to
employ formic acid in an excess based on V.
[0044] The compounds of the formula IB can be used to obtain the
compounds of the formula I in which R.sup.1 is NH--CO--A, where A
is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCH.sub.3. 6
[0045] The compounds of the formula IB are derivatized to give the
compounds of the formulae I.2 to I.6 by means of methods known from
the following documents, whose disclosure is herewith incorporated:
J. Med. Chem. (1989), Vol. 32, pp. 990-997; J. Org. Chem. (1961),
Vol. 26, p. 5238; J. Chem. Res. Synop. (1998), 442; Tetrahedron
Lett. (1994). Vol. 35, p. 8761.
[0046] The reaction of IB with alkali metal isocyanates or alkaline
earth metal isocyanates, in particular sodium isocyanate, to give
urea derivatives I.2 is carried out under the conditions known from
J. Med. Chem. (1989), Vol. 32, pp. 990-997.
[0047] The reaction of IB with methyl isocyanate to give urea
derivatives I.3 is carried out under the conditions known from J.
Org. Chem. (1961), Vol. 26, p. 5238.
[0048] The reaction of IB with dimethylamine and phosgene or a
phosgene equivalent such as di- or triphosgene to give urea
derivatives I.4 is carried out under the conditions known from J.
Chem. Res. Synop. (1998), 442. The use of di- or triphosgene is
preferred for practical reasons.
[0049] The reaction of IB with carbon monoxide and methanol to give
urea derivatives I.5 is carried out with transition metal catalysis
under the conditions known from Tetrahedron Lett. (1994), Vol. 35,
p. 8761.
[0050] Compounds of the formula I in which R.sup.1 is NH--CO--A
where A is C.sub.1-C.sub.4-alkyl can be obtained from the
aminophenol compounds of the formula IB by acylation with
alkylcarboxylic acid derivatives of the formula IV in which R.sup.4
is C.sub.1-C.sub.4-alkyl and Z is a nucleophilic leaving group such
as alkoxy or halogen. The acylamino derivatives are described by
the formula I.6 in which R.sup.4 is C.sub.1-C.sub.4-alkyl. 7
[0051] The acylation of V is carried out under conditions known per
se from the literature, it is usually carried out at temperatures
of from -20.degree. C. to +80.degree. C., preferably from 0.degree.
C. to +60.degree. C., in an inert organic solvent in the presence
of a base [cf. Organikum [Organic Chemistry), 15th Ed., p. 508 et
seq., VEB Deutscher Verlag der Wissenschaften Berlin (1981)].
[0052] Suitable solvents are water, aliphatic hydrocarbons,
aromatic hydrocarbons, halogenated hydrocarbons such as methylene
chloride, chloroform and chlorobenzene, ethers such as diethyl
ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole
and tetrahydrofuran, nitrites, ketones, alcohols, and also dimethyl
sulfoxide, dimethylformamide and dimethyl acetamide, especially
preferably tetrahydrofuran and methylene chloride. Mixtures of the
solvents stated may also be used.
[0053] Suitable bases are, in general, inorganic compounds such as
alkali metal hydroxides and alkaline earth metal hydroxides, alkali
metal oxides and alkaline earth metal oxides, alkali metal hydrides
and alkaline earth metal hydrides, alkali metal carbonates and
alkaline earth metal carbonates, alkali metal hydrogencarbonates
and also alkali metal alkoxides and alkaline earth metal alkoxides,
furthermore organic bases, for example tertiary amines such as
trimethylamine, triethylamine, tri-isopropylethylamine and
N-methylpiperidine, pyridine, substituted pyridines such as
collidin, lutidin and 4-dimethylaminopyridine, and bicyclic amines.
Pyridine and triethylamine are especially preferred. In general,
the bases are employed in equimolar amounts, in an excess or, if
appropriate, as a solvent.
[0054] In general, the starting materials are reacted with each
other in equimolar amounts. It may be advantageous for the yield to
employ the reactant(s) in an excess based on IB.
[0055] If individual compounds I are not accessible via the routes
described above, they can be prepared by derivatizing other
compounds I.
[0056] The reaction mixtures are worked up in the customary manner,
for example by mixing with water, separating the phases and, if
appropriate, purifying the crude products by chromatography. Some
of the intermediates and end products are obtained in the form of
colorless or pale brown, viscous oils, which are purified or freed
from volatile components under reduced pressure and at moderately
elevated temperature. If the intermediates and end products are
obtained as solids, they may also be purified by recrystallization
or digestion.
[0057] In the definitions of the symbols in the above formulae,
collective terms were used which generally represent the following
substituents:
[0058] halogen: fluorine, chlorine, bromine and iodine;
[0059] alkyl: saturated, straight-chain or branched hydrocarbon
radicals having 1 to 4, 6, 8 or 10 carbon atoms, for example
C.sub.1-C.sub.6-alkyl such as methyl, ethyl, propyl, 1-methylethyl,
butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl,
1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl,
1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl,
1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl,
1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl,
2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl,
1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,
1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and
1-ethyl-2-methylpropyl;
[0060] halogenalkyl: straight-chain or branched alkyl groups having
1 to 10 carbon atoms (as mentioned above), it being possible for
some or all of the hydrogen atoms in these groups to be replaced by
halogen atoms as mentioned above, for example
C.sub.1-C.sub.2-haloalkyl such as chloromethyl, bromomethyl,
dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,
trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl,
chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl,
2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,
2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,
2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and
pentafluoroethyl;
[0061] alkoxy: straight-chain or branched alkyl groups having 1 to
6 carbon atoms (as mentioned above) which are bonded to the
skeleton via an oxygen atom (--O--);
[0062] alkenyl: unsaturated, straight-chain or branched hydrocarbon
radicals having 2 to 4 or 6 carbon atoms and one double bond in any
position, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl,
1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl,
2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl,
1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl,
2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl,
2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,
2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl,
1,2-dimethyl-i-propenyl, 1,2-dimethyl-2-propenyl,
1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl,
3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl,
2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl,
1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl,
4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl,
3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,
2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl,
1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl,
1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl,
1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl,
1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl,
2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl,
2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl,
3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl,
1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl,
2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,
1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and
1-ethyl-2-methyl-2-propenyl;
[0063] alkynyl: straight-chain or branched hydrocarbon groups
having 2 to 4 or 6 carbon atoms and one triple bond in any
position, such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl,
2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl,
3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,
2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl,
1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl,
5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,
1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl,
3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl,
4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl,
1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl,
2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl,
1-ethyl-3-butynyl, 2-ethyl-3-butynyl and
1-ethyl-1-methyl-2-propynyl;
[0064] cycloalkyl: monocyclic saturated hydrocarbon groups saving 3
to 6 carbon ring members such as cyclopropyl, cyclobutyl,
cyclopentyl and cyclohexyl;
[0065] 5- or 6-membered heterocyclyl contains, in addition to
carbon ring members, one to three nitrogen atoms and/or one oxygen
or sulfur atom or one or two oxygen and/or sulfur atoms, e.g.
2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl,
3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl,
3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl,
3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,
3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl,
4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl,
5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,
1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,
1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,
1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,
1,3,4-thiadiazolidin-2-- yl, 1,3,4-triazolidin-2-yl,
2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl,
2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl,
2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl,
2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl,
2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl,
2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl,
2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl,
2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl,
2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl,
2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl,
2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl,
2,3-dihydropyrazol-3-yl- , 2,3-dihydropyrazol-4-yl,
2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl,
3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl- ,
3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl,
4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl,
4,5-dihydropyrazol-5-yl- , 2,3-dihydrooxazol-2-yl,
2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,
2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,
3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl,
3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,
3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,
3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl,
4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl,
4-hexahydropyridazinyl, 2-hexahydropyrimidinyl,
4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl,
1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl;
[0066] 5-membered heteroaryl contains one to four nitrogen atoms or
one to three nitrogen atoms and one sulfur or oxygen atom:
5-membered cyclic heteroaryl groups which, besides carbon atoms,
may contain one to four nitrogen atoms or one to three nitrogen
atoms and one sulfur or oxygen atom as ring members, e.g. 2-furyl,
3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl,
3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,
4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl,
5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,
4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl,
1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,
1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl,
1,3,4-thiadiazol-2-yl and 1,3,4-triazol-2-yl;
[0067] 6-membered heteroaryl contains one to three or one to four
nitrogen atoms: 6-membered cyclic heteroaryl groups which, besides
carbon atoms, may contain one to three or one to four nitrogen
atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,
3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,
5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl and
1,2,4-triazin-3-yl;
[0068] alkylene: divalent unbranched chains made up by 1 to 4
CH.sub.2 groups, e.g. CH.sub.2, CH.sub.2CH.sub.2,
CH.sub.2CH.sub.2CH.sub.2 and CH.sub.2CH.sub.2CH.sub.2CH.sub.2;
[0069] alkylenedioxy: divalent unbranched chains made up of 1 to 3
CH.sub.2 groups, both valencies being bound to the skeleton via an
oxygen atom, e.g. OCH.sub.2O, OCH.sub.2CH.sub.2O and
OCH.sub.2CH.sub.2CH.sub.2O.
[0070] With regard of the intended use of the salicylohydrazide
derivatives of the formula I, the following meanings of the
substituents are especially preferred, in each case alone or in
combination:
[0071] Especially preferred are compounds of the formula IA. 8
[0072] Especially preferred are compounds of the formula I where
R.sup.1 is NH--CO--A; these compounds are described with the
formula IC: 9
[0073] Also especially preferred are compounds I.1.
[0074] Equally, other preferred compounds are those of the formula
I.6 where R.sup.4 is methyl; these compounds are described by the
formula I.6a: 10
[0075] Besides, especially preferred compounds I are those where
the index m is zero; these compounds are described by the formula
ID: 11
[0076] In addition, especially preferred compounds I are those
where (X).sub.m is in the para-position relative to the phenol-OH
group and is halogen, NO.sub.2, CN and C.sub.1-C.sub.4-alkoxy, in
particular 4-chloro, 4-bromo and 4-NO.sub.2.
[0077] Equally especially preferred are compounds I where R.sup.2
is hydrogen, methyl, ethyl, n-propyl, isopropyl and cyano, in
particular hydrogen and methyl.
[0078] Other particularly preferred compounds I are those where
R.sup.3 is cyclohexyl and phenyl, each of which is optionally
substituted by one to three radicals R.sup.b, in particular phenyl.
In the case of compounds in which R.sup.3 is cyclohexyl, the
substituent R.sup.b can be in the E- or Z-position relative to the
C--R.sup.3 bond.
[0079] In addition, especially preferred compounds I are those
where R.sup.3 is pyrazolyl, pyrimidinyl, pyridinyl, pyrazinyl and
thiophenyl, each of which is optionally substituted by one to three
radicals R.sup.b.
[0080] The especially preferred use forms of the intermediates with
regard to the variables correspond to those of the radicals
(X).sub.m, R.sup.1, A, R.sup.2 and R.sup.3 of the formula I.
[0081] Especially preferred with regard to their use are the
compounds I which are compiled in the following tables. In the
tables, the groups mentioned for a substituent additionally
represent an especially preferred embodiment of the substituent in
question in their own right, independently of the combination in
which they are mentioned.
[0082] Table 1
[0083] Compounds of the formula IA where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 12
[0084] Table 2
[0085] Compounds of the formula IA where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0086] Table 3
[0087] Compounds of the formula IA where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0088] Table 4
[0089] Compounds of the formula IA where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0090] Table 5
[0091] Compounds of the formula IA where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0092] Table 6
[0093] Compounds of the formula IA where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0094] Table 7
[0095] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0096] Table 8
[0097] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0098] Table 9
[0099] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0100] Table 10
[0101] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0102] Table 11
[0103] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0104] Table 12
[0105] Compounds of the formula IA where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0106] Table 13
[0107] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0108] Table 14
[0109] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0110] Table 15
[0111] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0112] Table 16
[0113] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0114] Table 17
[0115] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0116] Table 18
[0117] Compounds of the formula IA where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0118] Table 19
[0119] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0120] Table 20
[0121] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0122] Table 21
[0123] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0124] Table 22
[0125] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0126] Table 23
[0127] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0128] Table 24
[0129] Compounds of the formula IA where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0130] Table 25
[0131] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0132] Table 26
[0133] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 or each compound
corresponds to one line of Table A
[0134] Table 27
[0135] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0136] Table 28
[0137] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0138] Table 29
[0139] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0140] Table 30
[0141] Compounds of the formula IA where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0142] Table 31
[0143] compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0144] Table 32
[0145] Compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0146] Table 33
[0147] Compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0148] Table 34
[0149] Compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0150] Table 35
[0151] Compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0152] Table 36
[0153] Compounds of the formula IA where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0154] Table 37
[0155] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0156] Table 38
[0157] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0158] Table 39
[0159] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0160] Table 40
[0161] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0162] Table 41
[0163] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0164] Table 42
[0165] Compounds of the formula IA where (X).sub.m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0166] Table 43
[0167] Compounds of the formula IA where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0168] Table 44
[0169] Compounds of the formula IA where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0170] Table 45
[0171] Compounds of the formula IA there (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0172] Table 46
[0173] Compounds of the formula IA where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0174] Table 47
[0175] Compounds of the formula IA where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0176] Table 48
[0177] Compounds of the formula IA where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0178] Table 49
[0179] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0180] Table 50
[0181] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0182] Table 51
[0183] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0184] Table 52
[0185] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0186] Table 53
[0187] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0188] Table 54
[0189] Compounds of the formula IA where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0190] Table 55
[0191] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0192] Table 56
[0193] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0194] Table 57
[0195] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0196] Table 58
[0197] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0198] Table 59
[0199] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0200] Table 60
[0201] Compounds of the formula IA where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0202] Table 61
[0203] Compounds of the formula IB where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 13
[0204] Table 62
[0205] Compounds of the formula IB where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0206] Table 63
[0207] Compounds of the formula IB where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0208] Table 64
[0209] Compounds of the formula IB where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0210] Table 65
[0211] Compounds of the formula IB where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0212] Table 66
[0213] Compounds of the formula IB where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0214] Table 67
[0215] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0216] Table 68
[0217] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0218] Table 69
[0219] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0220] Table 70
[0221] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0222] Table 71
[0223] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0224] Table 72
[0225] Compounds of the formula IB where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0226] Table 73
[0227] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0228] Table 74
[0229] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0230] Table 75
[0231] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0232] Table 76
[0233] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0234] Table 77
[0235] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0236] Table 78
[0237] Compounds of the formula IB where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0238] Table 79
[0239] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0240] Table 80
[0241] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0242] Table 81
[0243] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0244] Table 82
[0245] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0246] Table 83
[0247] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0248] Table 84
[0249] Compounds of the formula IB where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0250] Table 85
[0251] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0252] Table 86
[0253] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0254] Table 87
[0255] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0256] Table 88
[0257] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0258] Table 89
[0259] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0260] Table 90
[0261] Compounds of the formula IB where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0262] Table 91
[0263] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0264] Table 92
[0265] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0266] Table 93
[0267] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0268] Table 94
[0269] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0270] Table 95
[0271] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0272] Table 96
[0273] Compounds of the formula IB where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0274] Table 97
[0275] Compounds of the formula IB where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0276] Table 98
[0277] Compounds of the formula IB where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0278] Table 99
[0279] Compounds of the formula IB where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0280] Table 100
[0281] Compounds of the formula IB where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0282] Table 101
[0283] Compounds of the formula IB where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0284] Table 102
[0285] Compounds of the formula IB where (X).sub.m is 5-bromo.
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0286] Table 103
[0287] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0288] Table 104
[0289] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0290] Table 105
[0291] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0292] Table 106
[0293] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0294] Table 107
[0295] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0296] Table 108
[0297] Compounds of the formula IB where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0298] Table 109
[0299] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0300] Table 110
[0301] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0302] Table 111
[0303] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table
[0304] Table 112
[0305] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0306] Table 113
[0307] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0308] Table 114
[0309] Compounds of the formula IB where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0310] Table 115
[0311] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0312] Table 116
[0313] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0314] Table 117
[0315] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0316] Table 118
[0317] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0318] Table 119
[0319] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0320] Table 120
[0321] Compounds of the formula IB where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0322] Table 121
[0323] Compounds of the formula I.1 where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 14
[0324] Table 122
[0325] Compounds of the formula I.1 where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0326] Table 123
[0327] Compounds of the formula I.1 where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0328] Table 124
[0329] Compounds of the formula I.1 where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0330] Table 125
[0331] Compounds of the formula I.1 where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0332] Table 126
[0333] Compounds of the formula I.1 where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0334] Table 127
[0335] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0336] Table 128
[0337] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0338] Table 129
[0339] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0340] Table 130
[0341] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0342] Table 131
[0343] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0344] Table 132
[0345] Compounds of the formula I.1 where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0346] Table 133
[0347] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0348] Table 134
[0349] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0350] Table 135
[0351] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0352] Table 136
[0353] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0354] Table 137
[0355] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0356] Table 138
[0357] Compounds of the formula I.1 where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0358] Table 139
[0359] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0360] Table 140
[0361] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0362] Table 141
[0363] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0364] Table 142
[0365] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0366] Table 143
[0367] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0368] Table 144
[0369] Compounds of the formula I.1 where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0370] Table 145
[0371] Compounds of the formula I.1 where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0372] Table 146
[0373] Compounds of the formula I.1 where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0374] Table 147
[0375] Compounds of the formula I.1 where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0376] Table 148
[0377] Compounds of the formula I.1 where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0378] Table 149
[0379] Compounds of the formula I.1 where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0380] Table 150
[0381] Compounds of the formula I.1 where (X).sub.m is 3-bromo
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0382] Table 151
[0383] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0384] Table 152
[0385] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0386] Table 153
[0387] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0388] Table 154
[0389] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0390] Table 155
[0391] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0392] Table 156
[0393] Compounds of the formula I.1 where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0394] Table 157
[0395] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0396] Table 158
[0397] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0398] Table 159
[0399] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0400] Table 160
[0401] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0402] Table 161
[0403] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0404] Table 162
[0405] Compounds of the formula I.1 where (X).sub.m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0406] Table 163
[0407] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0408] Table 164
[0409] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0410] Table 165
[0411] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0412] Table 166
[0413] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0414] Table 167
[0415] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0416] Table 168
[0417] Compounds of the formula I.1 where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0418] Table 169
[0419] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0420] Table 170
[0421] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0422] Table 171
[0423] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0424] Table 172
[0425] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0426] Table 173
[0427] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0428] Table 174
[0429] Compounds of the formula I.1 where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0430] Table 175
[0431] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0432] Table 176
[0433] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0434] Table 177
[0435] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0436] Table 178
[0437] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.2 for each compound
corresponds to one line of Table A
[0438] Table 179
[0439] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0440] Table 180
[0441] Compounds of the formula I.1 where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0442] Table 181
[0443] Compounds of the formula I.2 where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 15
[0444] Table 182
[0445] Compounds of the formula I.2 where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0446] Table 183
[0447] Compounds of the formula I.2 where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0448] Table 184
[0449] Compounds of the formula I.2 where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0450] Table 185
[0451] Compounds of the formula I.2 where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0452] Table 186
[0453] Compounds of the formula I.2 where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0454] Table 187
[0455] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0456] Table 188
[0457] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0458] Table 189
[0459] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0460] Table 190
[0461] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0462] Table 191
[0463] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0464] Table 192
[0465] Compounds of the formula I.2 where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0466] Table 193
[0467] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0468] Table 194
[0469] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.2 for each compound
corresponds to one line of Table A
[0470] Table 195
[0471] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0472] Table 196
[0473] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0474] Table 197
[0475] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0476] Table 198
[0477] Compounds of the formula I.2 where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0478] Table 199
[0479] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0480] Table 200
[0481] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0482] Table 201
[0483] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0484] Table 202
[0485] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0486] Table 203
[0487] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0488] Table 204
[0489] Compounds of the formula I.2 where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.2 for each compound
corresponds to one line of Table A
[0490] Table 205
[0491] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0492] Table 206
[0493] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0494] Table 207
[0495] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0496] Table 208
[0497] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0498] Table 209
[0499] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0500] Table 210
[0501] Compounds of the formula I.2 where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0502] Table 211
[0503] Compounds of the formula I.2 where (X).sub.m is 4-bromo, 2
is hydrogen and the radical R.sup.3 for each compound corresponds
to one line of Table A
[0504] Table 212
[0505] Compounds of the formula I.2 where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0506] Table 213
[0507] Compounds of the formula I.2 where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0508] Table 214
[0509] Compounds of the formula I.2 where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0510] Table 215
[0511] Compounds of the formula I.2 where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0512] Table 216
[0513] Compounds of the formula I.2 where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0514] Table 217
[0515] Compounds of the formula I.2 where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0516] Table 218
[0517] Compounds of the formula I.2 where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0518] Table 219
[0519] Compounds of the formula I.2 where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0520] Table 220
[0521] Compounds of the formula I.2 where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0522] Table 221
[0523] Compounds of the formula I.2 where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0524] Table 222
[0525] Compounds of the formula I.2 where (X)hd m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0526] Table 223
[0527] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0528] Table 224
[0529] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0530] Table 225
[0531] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0532] Table 226
[0533] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0534] Table 227
[0535] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0536] Table 228
[0537] Compounds of the formula I.2 where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0538] Table 229
[0539] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0540] Table 230
[0541] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0542] Table 231
[0543] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0544] Table 232
[0545] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0546] Table 233
[0547] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0548] Table 234
[0549] Compounds of the formula I.2 where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0550] Table 235
[0551] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0552] Table 236
[0553] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0554] Table 237
[0555] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0556] Table 238
[0557] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0558] Table 239
[0559] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0560] Table 240
[0561] Compounds of the formula I.2 where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0562] Table 241
[0563] Compounds of the formula I.3 where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 16
[0564] Table 242
[0565] Compounds of the formula I.3 where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0566] Table 243
[0567] Compounds of the formula I.3 where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0568] Table 244
[0569] Compounds of the formula I.3 where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0570] Table 245
[0571] Compounds of the formula I.3 where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0572] Table 246
[0573] Compounds of the formula I.3 where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0574] Table 247
[0575] Compounds of the formula I.3 where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0576] Table 248
[0577] Compounds of the formula I.3 where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0578] Table 249
[0579] Compounds of the formula I.3 where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0580] Table 250
[0581] Compounds of the formula I.3 where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0582] Table 251
[0583] Compounds of the formula I.3 there (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0584] Table 252
[0585] Compounds of the formula I.3 where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0586] Table 253
[0587] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0588] Table 254
[0589] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0590] Table 255
[0591] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0592] Table 256
[0593] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0594] Table 257
[0595] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0596] Table 258
[0597] Compounds of the formula I.3 where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0598] Table 259
[0599] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0600] Table 260
[0601] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0602] Table 261
[0603] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0604] Table 262
[0605] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0606] Table 263
[0607] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0608] Table 264
[0609] Compounds of the formula I.3 where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0610] Table 265
[0611] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0612] Table 266
[0613] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0614] Table 267
[0615] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0616] Table 268
[0617] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0618] Table 269
[0619] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 as isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0620] Table 270
[0621] Compounds of the formula I.3 where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0622] Table 271
[0623] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0624] Table 272
[0625] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0626] Table 273
[0627] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0628] Table 274
[0629] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0630] Table 275
[0631] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0632] Table 276
[0633] Compounds of the formula I.3 where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0634] Table 277
[0635] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0636] Table 278
[0637] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0638] Table 279
[0639] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0640] Table 280
[0641] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0642] Table 281
[0643] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0644] Table 282
[0645] Compounds of the formula I.3 where (X).sub.m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0646] Table 283
[0647] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0648] Table 284
[0649] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0650] Table 285
[0651] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0652] Table 286
[0653] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0654] Table 287
[0655] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0656] Table 288
[0657] Compounds of the formula I.3 where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0658] Table 289
[0659] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0660] Table 290
[0661] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0662] Table 291
[0663] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0664] Table 292
[0665] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0666] Table 293
[0667] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0668] Table 294
[0669] Compounds of the formula I.3 where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0670] Table 295
[0671] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0672] Table 296
[0673] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0674] Table 297
[0675] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0676] Table 298
[0677] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0678] Table 299
[0679] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0680] Table 300
[0681] Compounds of the formula I.3 where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0682] Table 301
[0683] Compounds of the formula I.5 where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 17
[0684] Table 302
[0685] Compounds of the formula I.5 where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0686] Table 303
[0687] Compounds of the formula I.5 where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0688] Table 304
[0689] Compounds of the formula I.5 where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0690] Table 305
[0691] Compounds of the formula I.5 where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0692] Table 306
[0693] Compounds of the formula I.5 where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0694] Table 307
[0695] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0696] Table 308
[0697] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0698] Table 309
[0699] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0700] Table 310
[0701] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0702] Table 311
[0703] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0704] Table 312
[0705] Compounds of the formula I.5 where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0706] Table 313
[0707] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.2 for each compound
corresponds to one line of Table A
[0708] Table 314
[0709] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0710] Table 315
[0711] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0712] Table 316
[0713] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0714] Table 317
[0715] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0716] Table 318
[0717] Compounds of the formula I.5 where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0718] Table 319
[0719] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0720] Table 320
[0721] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0722] Table 321
[0723] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0724] Table 322
[0725] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0726] Table 323
[0727] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0728] Table 324
[0729] Compounds of the formula I.5 where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0730] Table 325
[0731] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0732] Table 326
[0733] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0734] Table 327
[0735] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0736] Table 328
[0737] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0738] Table 329
[0739] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0740] Table 330
[0741] Compounds of the formula I.5 where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0742] Table 331
[0743] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0744] Table 332
[0745] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0746] Table 333
[0747] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0748] Table 334
[0749] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0750] Table 335
[0751] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0752] Table 336
[0753] Compounds of the formula I.5 where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0754] Table 337
[0755] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0756] Table 338
[0757] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0758] Table 339
[0759] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0760] Table 340
[0761] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0762] Table 341
[0763] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0764] Table 342
[0765] Compounds of the formula I.5 where (X).sub.m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0766] Table 343
[0767] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0768] Table 344
[0769] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0770] Table 345
[0771] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0772] Table 346
[0773] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0774] Table 347
[0775] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0776] Table 348
[0777] Compounds of the formula I.5 where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0778] Table 349
[0779] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0780] Table 350
[0781] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0782] Table 351
[0783] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0784] Table 352
[0785] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0786] Table 353
[0787] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0788] Table 354
[0789] Compounds of the formula I.5 where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0790] Table 355
[0791] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0792] Table 356
[0793] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0794] Table 357
[0795] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0796] Table 358
[0797] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0798] Table 359
[0799] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0800] Table 360
[0801] Compounds of the formula I.5 where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0802] Table 361
[0803] Compounds of the formula I.6a where m is zero, R.sup.2 is
hydrogen and the radical R.sup.3 for each compound corresponds to
one line of Table A 18
[0804] Table 362
[0805] Compounds of the formula I.6a where m is zero, R.sup.2 is
methyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0806] Table 363
[0807] Compounds of the formula I.6a where m is zero, R.sup.2 is
ethyl and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0808] Table 364
[0809] Compounds of the formula I.6a where m is zero, R.sup.2 is
n-propyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0810] Table 365
[0811] Compounds of the formula I.6a where m is zero, R.sup.2 is
isopropyl and the radical R.sup.3 for each compound corresponds to
one line of Table A
[0812] Table 366
[0813] Compounds of the formula I.6a where m is zero, R.sup.2 is
cyano and the radical R.sup.3 for each compound corresponds to one
line of Table A
[0814] Table 367
[0815] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0816] Table 368
[0817] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0818] Table 369
[0819] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0820] Table 370
[0821] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0822] Table 371
[0823] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0824] Table 372
[0825] Compounds of the formula I.6a where (X).sub.m is 3-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0826] Table 373
[0827] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0828] Table 374
[0829] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0830] Table 375
[0831] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0832] Table 376
[0833] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0834] Table 377
[0835] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0836] Table 378
[0837] Compounds of the formula I.6a where (X).sub.m is 4-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0838] Table 379
[0839] Compounds of the formula I.6a where (X).sub.m is 5-chloro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0840] Table 380
[0841] Compounds of the formula I.6a where (X).sub.m is 5-chloro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0842] Table 381
[0843] Compounds of the formula I.6a where (X).sub.m is 5-chloro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0844] Table 382
[0845] Compounds of the formula I.6a where (X).sub.m is 5-chloro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0846] Table 383
[0847] Compounds of the formula I.6a where (X).sub.m is 5-chloro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0848] Table 384
[0849] Compounds of the formula I6a where (X).sub.m is 5-chloro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0850] Table 385
[0851] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0852] Table 386
[0853] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0854] Table 387
[0855] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0856] Table 388
[0857] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0858] Table 389
[0859] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0860] Table 390
[0861] Compounds of the formula I.6a where (X).sub.m is 3-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0862] Table 391
[0863] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0864] Table 392
[0865] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0866] Table 393
[0867] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0868] Table 394
[0869] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0870] Table 395
[0871] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0872] Table 396
[0873] Compounds of the formula I.6a where (X).sub.m is 4-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0874] Table 397
[0875] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0876] Table 398
[0877] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0878] Table 399
[0879] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0880] Table 400
[0881] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0882] Table 401
[0883] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0884] Table 402
[0885] Compounds of the formula I.6a where (X).sub.m is 5-bromo,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0886] Table 403
[0887] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0888] Table 404
[0889] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0890] Table 405
[0891] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0892] Table 406
[0893] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0894] Table 407
[0895] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0896] Table 408
[0897] Compounds of the formula I.6a where (X).sub.m is 3-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0898] Table 409
[0899] Compounds of the formula I.5a where (X).sub.m is 4-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0900] Table 410
[0901] Compounds of the formula I.6a where (X).sub.m is 4-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0902] Table 411
[0903] Compounds of the formula I.6a where (X).sub.m is 4-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0904] Table 412
[0905] Compounds of the formula I.6a where (X).sub.m is 4-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0906] Table 413
[0907] Compounds of the formula I.6a where (X).sub.m is 4-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0908] Table 414
[0909] Compounds of the formula I.6a where (X).sub.m is 4-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0910] Table 415
[0911] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is hydrogen and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0912] Table 416
[0913] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is methyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0914] Table 417
[0915] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is ethyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0916] Table 418
[0917] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is n-propyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0918] Table 419
[0919] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is isopropyl and the radical R.sup.3 for each compound
corresponds to one line of Table A
[0920] Table 420
[0921] Compounds of the formula I.6a where (X).sub.m is 5-nitro,
R.sup.2 is cyano and the radical R.sup.3 for each compound
corresponds to one line of Table A
1TABLE A I 19 No. R.sup.3 R.sup.b A-1 c-C.sub.6H.sub.11 -- A-2
c-C.sub.6H.sub.10 2-Cl A-3 c-C.sub.6H.sub.10 3-Cl A-4
c-C.sub.6H.sub.10 4-Cl A-5 c-C.sub.6H.sub.10 2-Br A-6
c-C.sub.6H.sub.10 3-Br A-7 c-C.sub.6H.sub.10 4-Br A-8
c-C.sub.6H.sub.10 2-NO.sub.2 A-9 c-C.sub.6H.sub.10 3-NO.sub.2 A-10
c-C.sub.6H.sub.10 4-NO.sub.2 A-11 c-C.sub.6H.sub.10 4-NO.sub.2 A-11
c-C.sub.6H.sub.10 2-CN A-12 c-C.sub.6H.sub.10 3-CN A-13
c-C.sub.6H.sub.10 4-CN A-14 c-C.sub.6H.sub.10 2-CH.sub.3 A-15
c-C.sub.6H.sub.10 3-CH.sub.3 A-16 c-C.sub.6H.sub.10 4-CH.sub.3 A-17
c-C.sub.6H.sub.9 2,4-(Cl).sub.2 A-18 c-C.sub.6H.sub.9
2,4-(Br).sub.2 A-19 c-C.sub.6H.sub.9 2,4-(NO.sub.2).sub.2 A-20
c-C.sub.6H.sub.9 2,4-(CH.sub.3).sub.2 A-21 c-C.sub.6H.sub.10
4-CH.sub.2CH.sub.3 A-22 c-C.sub.6H.sub.10
4-CH.sub.2CH.sub.2CH.sub.3 A-23 c-C.sub.6H.sub.10
4-CH(CH.sub.3).sub.2 A-24 c-C.sub.6H.sub.10
4-CH.sub.2CH.sub.2CH.sub.2CH.sub.3 A-25 c-C.sub.6H.sub.10
4-CH.sub.2CH(CH.sub.3).sub.2 A-26 C.sub.6H.sub.5 -- A-27
C.sub.6H.sub.4 2-Cl A-28 C.sub.5H.sub.4 3-Cl A-29 C.sub.6H.sub.4
4-Cl A-30 C.sub.6H.sub.4 2-Br A-31 C.sub.6H.sub.4 3-Br A-32
C.sub.6H.sub.4 4-Br A-33 C.sub.6H.sub.4 2-NO.sub.2 A-34
C.sub.6H.sub.4 3-NO.sub.2 A-35 C.sub.6H.sub.4 4-NO.sub.2 A-36
C.sub.6H.sub.4 2-CN A-37 C.sub.6H.sub.4 3-CN A-38 C.sub.6H.sub.4
4-CN A-39 C.sub.6H.sub.4 2-CH.sub.3 A-40 C.sub.6H.sub.4 3-CH.sub.3
A-41 C.sub.6H.sub.4 4-CH.sub.3 A-42 C.sub.6H.sub.4
4-CH.sub.2CH.sub.3 A-43 C.sub.6H.sub.4 4-CH.sub.2CH.sub.2CH.sub.3
A-44 C.sub.6H.sub.4 4-CH(CH.sub.3).sub.2 A-45 C.sub.5H.sub.4
4-CH.sub.2CH.sub.2CH.sub.2CH.sub.3 A-46 C.sub.6H.sub.4
4-CH.sub.2CH(CH.sub.3).sub.2 A-47 C.sub.6H.sub.4
4-C(CH.sub.3).sub.3 A-48 C.sub.6H.sub.4 4-C.sub.6H.sub.5 A-49
C.sub.6H.sub.4 4-(2-Cl)--C.sub.6H.sub.4 A-50 C.sub.6H.sub.4
4-(3-Cl)--C.sub.6H.sub.4 A-51 C.sub.6H.sub.4
4-(4-Cl)--C.sub.6H.sub.4 A-52 C.sub.6H.sub.4
4-(2-Br)--C.sub.6H.sub.4 A-53 C.sub.6H.sub.4
4-(3-Br)--C.sub.6H.sub.4 A-54 C.sub.6H.sub.4
4-(4-Br)--C.sub.6H.sub.4 A-55 C.sub.6H.sub.4
4-(2-NO.sub.2)--C.sub.6H.sub.4 A-56 C.sub.6H.sub.4
4-(3-NO.sub.2)--C.sub.6H.sub.4 A-57 C.sub.6H.sub.4
4-(4-NO.sub.2)--C.sub.6H.sub.4 A-58 C.sub.6H.sub.4
4-(2-CN)--C.sub.6H.sub.4 A-59 C.sub.6H.sub.4
4-(3-CN)--C.sub.6H.sub.4 A-60 C.sub.6H.sub.4
4-(4-CN)--C.sub.6H.sub.4 A-61 C.sub.6H.sub.4
4-(2-CH.sub.3)--C.sub.6H.sub.4 A-62 C.sub.6H.sub.4
4-(3-CH.sub.3)--C.sub.6H.sub.4 A-63 C.sub.6H.sub.4
4-(4-CH.sub.3)--C.sub.6H.sub.4 A-64 C.sub.6H.sub.4
4-(2,4-Cl.sub.2)--C.sub.6H.sub.3 A-65 C.sub.6H.sub.4
4-(2,4-Br.sub.2)--C.sub.6H.sub.3 A-66 C.sub.6H.sub.4
4-[2,4-(NO.sub.2).sub.2]--C.sub.6H.sub.3 A-67 C.sub.6H.sub.4
4-[2,4-(CH.sub.3).sub.2]--C.sub.6H.sub.3
[0922] The compounds I are suitable as fungicides. They are
distinguished by an outstanding activity against a broad spectrum
of phytopathogenic fungi, in particular from the classes of the
Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes. Some
of them act systemically, and they can be employed in crop
protection as foliar-acting and soil-acting fungicides. They are
especially important for controlling a multiplicity of fungi on a
series of crop plants such as wheat, rye, barley, oats, rice,
maize, grass, bananas, cotton, soya, coffee, sugar cane,
grapevines, fruit plants, ornamentals and vegetable plants such as
cucumbers, beans, tomatoes, potatoes and cucurbits, and on the
seeds of these plants.
[0923] Specifically, they are suitable for controlling the
following plant diseases:
[0924] Alternaria species on vegetable and fruit,
[0925] Botrytis cinerea (gray mold) on strawberries, vegetables,
ornamentals and grapevines,
[0926] Cercospora arachidicola on peanuts,
[0927] Erysiphe cichoracearum and Sphaerotheca fuliginea on
cucurbits,
[0928] Erysiphe graminis (powdery mildew) on cereals,
[0929] Fusarium and Verticillium species on a variety of
plants,
[0930] Helminthosporium species on cereals,
[0931] Mycosphaerella species on bananas and peanuts,
[0932] Phytophthora infestans on potatoes and tomatoes,
[0933] Plasmopara viticola on grapevines,
[0934] Podosphaera leucotricha on apples,
[0935] Pseudocercosporella herpotrichoides on wheat and barley,
[0936] Pseudoperonospora species on hops and cucumbers,
[0937] Puccinia species on cereals,
[0938] Pyricularia oryzae on rice,
[0939] Rhizoctonia species on cotton, rice and lawns,
[0940] Septoria nodorum on wheat,
[0941] Uncinula necator on grapevines,
[0942] Ustilago species on cereals and sugar cane, and
[0943] Venturia species (scab) on apples and pears.
[0944] Moreover, the compounds I are suitable for controlling
harmful fungi such as Paecilomyces variotii in the protection of
materials (for example wood, paper, paint dispersions, fibers and
fabrics) and in the protection of stored products.
[0945] The compounds I are applied by treating the fungi, or the
plants, seeds, materials to be protected against fungal infection,
or the soil, with a fungicidally effective amount of the active
ingredients. Application can be effected both before and after
infection of the materials, plants or seeds by the fungi.
[0946] In general, the fungicidal compositions comprise from 0.1 to
95, preferably from 0.5 to 90, % by weight of active
ingredient.
[0947] When used in crop protection, the application rates are from
0.01 to 2.0 kg of active ingredient per ha, depending on the nature
of the desired effect.
[0948] In the treatment of seed, amounts of active ingredient of
from 0.001 to 0.1 g, preferably 0.01 to 0.05 g, are generally
required per kilogram of seed.
[0949] When used in the protection of materials or stored products,
the application rate of active ingredient depends on the nature of
the field of application and on the desired effect. Conventionally
used application rates in the protection of materials are, for
example, from 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of
active ingredient per cubic meter of material treated.
[0950] The compounds I can be converted into the customary
formulations, e.g. solutions, emulsions, suspensions, dusts,
powders, pastes and granules. The use form depends on the
particular purpose; it is intended to ensure in each case a fine
and uniform distribution of the compound according to the
invention.
[0951] The formulations are prepared in a known manner, e.g. by
extending the active ingredient with solvents and/or carriers, if
desired using emulsifiers and dispersants, it also being possible
to use other organic solvents as cosolvents if water is used as the
diluent. Auxiliaries which are suitable are essentially: solvents
such as aromatics (e.g. xylene), chlorinated aromatics (e.g.
chlorobenzenes), paraffins (e.g. mineral oil fractions), alcohols
(e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines
(e.g. ethanolamine, dimethylformamide) and water; carriers such as
ground natural minerals (e.g. kaolins, clays, talc, chalk) and
ground synthetic minerals (e.g. highly dispersed silica,
silicates); emulsifiers such as nonionic and anionic emulsifiers
(e.g., polyoxyethylene fatty alcohol ethers, alkylsulfonates and
arylsulfonates) and dispersants such as lignin-sulfite waste
liquors and methylcellulose.
[0952] Suitable surfactants are alkali metal, alkaline earth metal
and ammonium salts of lignosulfonic acid, napthalenesulfonic acid,
phenolsulfonic acid, dibutylnaphthalenesulfonic acid,
alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol
sulfates and fatty acids and their alkali metal and alkaline earth
metal salts, salts of sulfated fatty alcohol glycol ether,
condensates of sulfonated naphthalene and napthalene derivatives
with formaldehyde, condensates of napthalene or of
naphthalenesulfonic acid with phenol and formaldehyde,
polyoxyethylene octylphenyl ether, ethoxylated isooctyl phenol,
octyl phenol, nonyl phenol, alkyl phenyl polyglycol ethers,
tributylphenyl polyglycol ether, alkylaryl polyether alcohols,
isotridecyl alcohol, fatty alcohol/ethylene oxide condensates,
ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated
polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol
esters, lignin sulfite waste liquors and methyl cellulose.
[0953] Substances which are suitable for the preparation of
directly sprayable solutions, emulsions, pastes or oil dispersions
are mineral oil fractions of medium to high boiling point, such as
kerosene or diesel oil, furthermore coal tar oils and oils of
vegetable or animal origin, aliphatic, cyclic and aromatic
hydrocarbons, e.g. benzene, toluene, xylene, paraffin,
tetrahydronaphthalene, alkylated naphthalenes or their derivatives,
methanol, ethanol, propanol, butanol, chloroform, carbon
tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene,
isophorone, strongly polar solvents, e.g. dimethylformamide,
dimethyl sulfoxide, N-methylpyrrolidone and water.
[0954] Powders, materials for spreading and dusts can be prepared
by mixing or concomitantly grinding the active substances together
with a solid carrier.
[0955] Granules, e.g. coated granules, impregnated granules and
homogeneous granules, can be prepared by binding the active
ingredients to solid carriers. Examples of solid carriers are
mineral earths, such as silica gels, silicic acids, talc, kaolin,
attaclay, limestone, lime, chalk, bole, loess, clay, dolomite,
diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium
oxide, ground synthetic materials, fertilizers, e.g. ammonium
sulfate, ammonium phosphate, ammonium nitrate, ureas, and products
of vegetable origin, such as cereal meal, tree bark meal, wood meal
and nutshell meal, cellulose powders and other solid carriers.
[0956] In general, the formulations comprise from 0.01 to 95% by
weight, preferably from 0.1 to 90% by weight, of the active
ingredient. The active ingredients are employed in a purity of from
90% to 100%, preferably 95% to 100% (according to NMR
spectrum).
[0957] The following are examples of formulations:
[0958] I. 5 parts by weight of a compound according to the
invention are mixed intimately with 95 parts by weight of finely
divided kaolin. This gives a dust which comprises 5% by weight of
the active ingredient.
[0959] II. 30 parts by weight of a compound according to the
invention are mixed intimately with a mixture of 92 parts by weight
of pulverulent silica gel and 8 parts by weight of paraffin oil
which had been sprayed onto the surface of this silica gel. This
gives a formulation of the active ingredient with good adhesion
properties (active ingredient content 23% by weight).
[0960] III. 10 parts by weight of a compound according to the
invention are dissolved in a mixture composed of 90 parts by weight
of xylene, 6 parts by weight of the adduct of 8 to 10 mol of
ethylene oxide and 1 mol of oleic acid N-monoethanolamide, 2 parts
by weight of calcium dodecylbenzenesulfonate and 2 parts by weight
of the adduct of 40 mol of ethylene oxide and 1 mol of castor oil
(active ingredient content 9% by weight)
[0961] IV. 20 parts by weight of a compound according to the
invention are dissolved in a mixture composed of 60 parts by weight
of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by
weight of the adduct of 7 mol of ethylene oxide and 1 mol of
isooctylphenol and 5 parts by weight of the adduct of 40 mol of
ethylene oxide and 1 mol of castor oil (active ingredient content
16% by weight).
[0962] V. 80 parts by weight of a compound according to the
invention are mixed thoroughly with 3 parts by weight of sodium
diisobutylnaphthalene-a- lpha-sulfonate, 10 parts by weight of the
sodium salt of a lignosulfonic acid from a sulfite waste liquor and
7 parts by weight of pulverulent silica gel, and the mixture is
ground in a hammer mill (active ingredient content 80% by
weight).
[0963] VI. 90 parts by weight of a compound according to the
invention are mixed with 10 parts by weight of
N-methyl-.alpha.-pyrrolidone, which gives a solution which is
suitable for use in the form of microdrops (active ingredient
content 90% by weight).
[0964] VII. 20 parts by weight of a compound according to the
invention are dissolved in a mixture composed of 40 parts by weight
of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by
weight of the adduct of 7 mol of ethylene oxide and 1 mol of
isooctylphenol and 10 parts by weight of the adduct of 40 mol of
ethylene oxide and 1 mol of castor oil. Pouring the solution into
100,000 parts by weight of water and finely distributing it therein
gives an aqueous dispersion comprising 0.02% by weight of the
active ingredient.
[0965] VIII. 20 parts by weight of a compound according to the
invention are mixed thoroughly with 3 parts by weight of sodium
diisobutylnaphthalene-.alpha.-sulfonate, 17 parts by weight of the
sodium salt of a lignosulfonic acid from a sulfite waste liquor and
60% by weight of pulverulent silica gel, and the mixture is ground
in a hammer mill. Finely distributing the mixture in 20,000 parts
by weight of water gives a spray mixture comprising 0.1% by weight
of the active ingredient.
[0966] The active ingredients can be used as such, in the form of
their formulations or the use forms prepared therefrom, e.g. in the
form of directly sprayable solutions, powders, suspensions or
dispersions, emulsions, oil dispersions, pastes, dusts, materials
for spreading, or granules, by means of spraying, atomizing,
dusting, spreading or pouring. The use forms depend entirely on the
intended purposes; they are intended to ensure in each case the
finest possible distribution of the active ingredients according to
the invention.
[0967] Aqueous use forms can be prepared from emulsion
concentrates, pastes or wettable powders (sprayable powders, oil
dispersions) by adding water. To prepare emulsions, pastes or oil
dispersions, the substances, as such or dissolved in an oil or
solvent, can be homogenized in water by means of wetter, tackifier,
dispersant or emulsifier. Alternatively, it is possible to prepare
concentrates composed of active substance, wetter, tackifier,
dispersant or emulsifier and, if appropriate, solvent or oil, and
such concentrates are suitable for dilution with water.
[0968] The active ingredient concentration in the ready-to-use
products can be varied within relatively wide ranges. In general,
they are from 0.0001 to 10%, preferably from 0.01 to 1%.
[0969] The active ingredients may also be used successfully in the
ultra-low-volume process (ULV), it being possible to apply
formulations comprising over 95% by weight of active ingredient, or
even to apply the active ingredient without additives.
[0970] Various types of oils, or herbicides, fungicides, other
pesticides or bactericides may be added to the active ingredients,
if appropriate just immediately prior to use (tank mix). These
agents can be admixed with the agents according to the invention in
a weight ratio of 1:10 to 10:1.
[0971] In the use form as fungicides, the compositions according to
the invention can also be present together with other active
ingredients, e.g. with herbicides, insecticides, growth regulators,
fungicides or else with fertilizers. Mixing the compounds I or the
compositions comprising them in the use form as fungicides with
other fungicides frequently results in a broadened fungicidal
spectrum of action.
[0972] The following list of fungicides together with which the
compounds according to the invention can be used is intended to
illustrate the possible combinations, but not to impose any
limitation:
[0973] sulfur, dithiocarbamates and their derivatives, such as iron
(III) dimethyldithiocarbamate, zinc dimethyldithiocarbamate, zinc
ethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,
manganese zinc ethylenediaminebisdithiocarbamate,
tetramethylthiuram disulfide, ammonia complex of zinc
(N,N-ethylenebisdithiocarbamate), ammonia complex of zinc
(N,N'-propylenebisdithiocarbamate), zinc
(N,N'-propylenebisdithiocarbamate),
N,N'-polypropylenebis(thiocarbamoyl)d- isulfide;
[0974] nitro derivatives, such as dinitro(1-methylheptyl)phenyl
crotonate, 2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,
2-sec-butyl-4,6-dinitrophenylisopropyl carbonate, diisopropyl
5-nitroisophthalate;
[0975] heterocyclic substances, such as 2-heptadecyl-2-imidazoline
acetate, 2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethyl
phthalimidophosphonothioate,
5-amino-1-[bis(dimethylamino)phosphinyl]-3-p- henyl-1,2,4-triazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl
1-(butylcarbamoyl)-2-benzim- idazolecarbamate,
2-methoxycarbonylaminobenzimidazole, 2-(2-furyl)-benzimidazole,
2-(4-thiazolyl)benzimidazole,
N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,
N-tri-chloromethylthiotetrahydrophthalimide,
N-trichloromethylthiophthali- mide;
[0976]
N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfo-diamide,
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-thiocyanatomethylthiobenz- othiazole,
1,4-dichloro-2,5-dimethoxybenzene, 4-(2-chlorophenylhydrazono)--
3-methyl-5-isoxazolone, pyridine-2-thiol 1-oxide,
8-hydroxyquinoline or its copper salt,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine 4,4-dioxide,
2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,
2-methylfuran-3-carboxanil- ide, 2,5-dimethylfuran-3-carboxanilide,
2,4,5-trimethylfuran-3-carboxanili- de,
N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,
N-cyclohexyl-N-methoxy-2- ,5-dimethylfuran-3-carboxamide,
2-methylbenzanilide, 2-iodobenzanilide,
N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,
piperazine-1,4-diylbis-1-(2,2,2-trichloroethyl)formamide,
1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane;
[0977] amines such as 2,6-dimethyl-N-tridecylmorpholine or its
salts, 2,6-dimethyl-N-cyclododecylmorpholine or its salts,
N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethyl-morpholine,
N-[3- (p-tert-butylphenyl)-2-methylpropyl]-piperidine;
[0978] azoles such as
1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yle-
thyl]-1H-1,2,4-triazole,
1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-
-2-ylethyl]-1H-1,2,4-triazole,
N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl- )-N'-imidazolylurea,
1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol--
1-yl)-2-butanone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-
(1H-1,2,4-triazol-1-yl) -2-butanol,
(2RS,3RS)-1-[3-(2-chlorophenyl)-2-(4--
fluorophenyl)oxiran-2-yl-methyl]-1H-1,2,4-triazole,
.alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-5-pyrimidinemethanol,
5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,
bis(p-chlorophenyl)-3-pyridinemethanol,
1,2-bis(3-ethoxycarbonyl-2-thiour- eido)benzene,
1,2-bis(3-methoxycarbonyl-2-thioureido)benzene;
[0979] strobilurins such as methyl
E-methoxyimino-[.alpha.-(o-tolyloxy)-o-- tolyl]acetate, methyl
E-2-{2-[6-(2-cyanophenoxy)pyrimidin-4-yloxylphenyl}--
3-methoxyacrylate,
N-methyl-E-methoxy-imino-[.alpha.-(2-phenoxyphenyl)]ace- tamide,
N-methyl E-methoxyimino-(.alpha.-(2,5-dimethylphenoxy)-o-tolyl]ace-
tamide;
[0980] anilinopyrimidines such as
N-(4,6-dimethylpyrimidin-2-yl)aniline,
N-[4-methyl-6-(1-propynyl)pyrimidin-2-yl]aniline,
N-[4-methyl-6-cycloprop- ylpyrimidin-2-yl]aniline;
[0981] phenylpyrroles such as
4-(2,2-difluoro-1,3-benzodioxol-4-yl)pyrrole- -3-carbonitrile;
[0982] cinnanamides such as
3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acry- loylmorpholine;
[0983] and a variety of fungicides such as dodecylguanidine
acetate,
3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,
hexachlorobenzene, methyl
N-(2,6-dimethylphenyl)-N-(2-furoyl)-DL-alaninat- e,
DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methyl ester,
N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,
DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,
5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,
3-(3,5-dichlorophenyl)5-methyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione,
3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,
N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,
2-cyano-[N-(ethylaminocarbonyl)-2-methoximino]acetamide,
1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,
2,4-difluoro-.alpha.- (1H-1,2,4-triazolyl-1-methyl)benzhydryl
alcohol, N-(3-chloro-2,6-dinitro--
4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridin,
1-((bis-(4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.
SYNTHESIS EXAMPLES
[0984] The protocols shown in the synthesis examples herebelow were
used for obtaining further compounds I, except that the starting
compounds were changed as appropriate. The resulting compounds are
listed in the tables which follow together with physical data.
Example 1
Preparation of 2-hydroxy-3-nitrobenzhydrazide
[0985] 20
[0986] 40 ml of hydrazine hydrate were added to a solution of 30 g
(0.15 mol) of methyl 3-nitrosalicylate in 200 ml of anhydrous
tetrahydrofuran (THF). After dilution with THF, the resulting
suspension was stirrable; it was refluxed for approximately 18
hours. After cooling, the batch was poured onto ice. The aqueous
solution was rendered neutral by adding NaOH solution. The crystals
which precipitated were filtered off and washed with water. After
drying, 27 g (90%) of the title compound were obtained.
Example 2
Preparation of 3-nitrosalicylic (1-phenylethylidene)hydrazide
[0987] 21
[0988] A solution of 1.0 g (5 mmol) of 3-nitrosalicylohydrazide in
50 ml of anhydrous ethanol were treated with 0.6 g (5 mmol) of
acetophenone and with a catalytic amount of p-toluenesulfonic acid.
After the mixture had been stirred for 14 hours at approximately 20
to 25.degree. C. and the solvent had been distilled off, 1.4 g of
the title compound (90% of theory) were obtained as colorless
crystals of m.p.: 163-168.degree. C.
2TABLE I I 22 No. R.sup.1 (X).sub.m R.sup.2 R.sup.3 M.p. [.degree.
C.] I-1 NO.sub.2 H CH.sub.3 C.sub.6H.sub.5 163-168 I-2 NO.sub.2 H H
C.sub.6H.sub.5 193-199 I-3 NO.sub.2 H CH.sub.3
4-CH.sub.3--C.sub.6H.sub.4 149-154 I-4 NO.sub.2 H H
4-CH.sub.3--C.sub.6H.sub.4 160-166 I-5 NO.sub.2 H CH.sub.3
4-Cl--C.sub.6H.sub.4 194-197 I-6 NO.sub.2 H H 4-Cl--C.sub.6H.sub.4
192-196 I-7 NO.sub.2 H CH.sub.3 4-Br--C.sub.6H.sub.4 194-197 I-8
NO.sub.2 H H 4-Br--C.sub.6H.sub.4 174-178 I-9 NO.sub.2 H CH.sub.3
4-NO.sub.2--C.sub.6H.sub.4 204-208 I-10 NO.sub.2 H H
4-NO.sub.2--C.sub.6H.sub.4 240-244 I-11 NO.sub.2 H CH.sub.3
4-CN--C.sub.6H.sub.4 218-222 I-12 NO.sub.2 H H 4-CN--C.sub.6H.sub.4
220-223 I-13 NO.sub.2 H CH.sub.3 4-OCH.sub.3--C.sub.6H.sub.4
146-150 I-14 NO.sub.2 H H 4-OCH.sub.3--C.sub.6H.sub.4 167-172 I-15
NO.sub.2 H CH.sub.3 2,4-(OCH.sub.3).sub.2--C.sub.6H.sub.4 245-248
I-16 NO.sub.2 H H 2,4-(OCH.sub.3).sub.2--C.sub.6H.sub.4 207-210
I-17 NO.sub.2 H CH.sub.3 2,4-Cl.sub.2--C.sub.6H.sub.4 110-114 I-18
NO.sub.2 H H 2,4-Cl.sub.2--C.sub.6H.sub.4 219-223 I-19 NO.sub.2 H
CH.sub.3 4-C.sub.6H.sub.5--C.sub.6H.sub.4 209-212 I-20 NO.sub.2 H H
4-C.sub.6H.sub.5--C.sub.6H.sub.4 189-195
[0989] Examples of the action against harmful fungi
[0990] The fungicidal action of the compounds of the general
formula I was demonstrated by the following experiments:
[0991] The active ingredients, separately or together, were
formulated as a 10% emulsion in a mixture of 70% by weight of
cyclohexanone, 20% by weight of Nekanil.RTM. LN (Lutensol.RTM. AP6,
wetter with emulsifier and dispersant action based on ethoxylated
alkylphenols) and 10% by weight of Wettol.RTM. EM (nonionic
emulsifer based on ethoxylated castor oil) and the formulations
were diluted with water to give the desired concentration.
[0992] Use example--activity against Botrytis cinerea on capsicum
leaves
[0993] After 4-5 leaves had developed properly, capsicum seedlings
cv. "Neusiedler Ideal Elite" were sprayed to runoff point with an
aqueous preparation of active ingredient made with a stock solution
of 10% of active ingredient, 63% of cyclohexanone and 27% of
emulsifier. Next day, the treated plants were inoculated with a
spore suspension of Botrytis cinerea which contained
1.7.times.10.sup.6 spores/ml in a 2% strength aqueous Biomite
solution. The test plants were subsequently placed into a
controlled-environment cabinet at 22-24.degree. C. and high
atmospheric humidity. After 5 days, it was possible to determine
the extent of fungal infection on the leaves visually in %.
[0994] In this test, the disease level of the plants treated with a
250 ppm formulation of the active ingredient I-1, I-3 and I-6 was
not more than 15%, while it was 90% in the case of the untreated
plants.
* * * * *