DE19834557A1 - New (hetero)aryl 1,2,4-triazole or isoxazole derivatives useful as fungicides, insecticides, acaricides and nematocides - Google Patents

Abstract

(Hetero)aryl 1,2,4-triazole or isoxazole derivatives (I) are new. (Hetero)aryl derivatives of formula (I) are new. X, Y, Z = N or CR<1>; R<1> = H, CN, NO2, halogen, 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy, 1-4C alkylthio or 1-4C haloalkylthio; V = CH2, NRa, O, S, CO or C(=CRa2); Ra = H or 1-4C alkyl; W = a group of formula (A) or (B): RA = halogen, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, E or NRaRb; E = alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heterocyclyl, aryl or heteroaryl, all optionally substituted; Rb = H or 1-4C alkyl; RB = O or S; RC = H or 1-4C alkyl; U = a bond, O or OCH2; G = either (a) D, -N=CR<2>-E, -N=CR<2>-CR<3>=N-OR<4> or -N=CR<2>-C(=NOR<4>)-CR<3>=NOR<4> when U is O or OCH2 or (b) E, CH2CH2E, CH=CHE, C?=CE, SE, CH2SE, C(Ra)=NOCH2E, CH2OC(O)E, CH2OC(Me)=N-N=C(Me)-E or CH2NReRf when U is a bond; D = heterocyclyl, aryl, heteroaryl, arylmethyl or heteroarylmethyl, all optionally substituted; R<2> = H, CN, 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, (1-4C)alkoxy(1-4C)alkyl or 3-6C cycloalkyl; R<3> = H, CN, halogen, E, OE, SE or N(Rd)E; Rd = H, 1-4C alkyl, 2-6C alkenyl or 2-6C alkynyl; R<4> = H or optionally substituted 1-4C alkyl, 3-6C cycloalkyl, 2-6C alkenyl or 2-6C alkynyl; and Re, Rf = as R<4> or together with N form a heterocyclyl or heteroaryl group. Independent claims are also included for the following: (1) processes for preparing (I; W=A) and (I; W=B); and (2) intermediates of formula (II)-(IV). Q = Me, halomethyl, OH or L, but not OH when Q'' is -N=C=RB; L = a nucleophilically cleavable group; Q'' = -N=C=RB, -NH-C(=RB)-NH-N(RC)2 or A; Q' = Me, halomethyl, OH or L, but not OH in (III); R' = 1-6C alkyl or optionally substituted phenyl.

Description

The present invention relates to (hetero) aryl compounds of the formula I,

in which the substituents have the following meaning
X, Y, Z independently of one another = N- or = CR ¹ -, where
R ^{1 can be the} same or different and hydrogen, cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ Are -C ₄ alkylthio or C ₁ -C ₄ haloalkylthio;
V -CH ₂ -, NR ^a -, -O-, -S-, -C (= O) - or -C (= CR ^a R ^b ) -, where
R ^a , R ^b independently of one another are hydrogen or C ₁ -C ₄ alkyl;
W is a group A or B,

in the
# indicates the bond with group V and
R ^A for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, a group E or NR ^a R ^b , wherein
E if necessary subst. Alkyl, optionally subst. Alkenyl, if necessary subst. Alkynyl, optionally subst. Cycloalkyl, optionally subst. Cycloal kenyl, optionally subst. Heterocyclyl, optionally subst. Aryl or optionally subst. Hetaryl,
R ^a , R ^{b are} independently hydrogen or C ₁ -C ₄ alkyl;
R ^B for oxygen or sulfur and
R ^{C is} hydrogen or C ₁ -C ₄ alkyl;
U is a direct bond, oxygen or oxymethylene (-OCH ₂ -);
G a) if U is oxygen or oxymethylene, a group D, EC (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N or R ⁴ ON = C (C [R ³ ] = N-OR ⁴ ) -C (R ² ) = N, where
D if necessary subst. Heterocyclyl, optionally subst. Aryl, if necessary subst. Hetaryl, possibly subst. Arylmethylene or optionally subst. Het arylmethylene;
E if necessary subst. Alkyl, optionally subst. Alkenyl, if necessary subst. Alki nyl, if necessary subst. Cycloalkyl, optionally subst. Cycloalkenyl, optionally subst. Heterocyclyl, optionally subst. Aryl or optionally subst. Hetaryl;
R ^{2 is} hydrogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₃ -C _6- cycloalkyl;
R ^{3 is} hydrogen, cyano, halogen, R ⁴ ON = C (R ^a ) or E, EO, ES or EN (R ^d ), where
R ^{d is} hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkyl,
R ⁴ hydrogen, optionally subst. C ₁ -C ₄ alkyl, optionally subst. C ₃ -C ₆ cycloalkyl, optionally subst. C ₂ -C ₆ alkenyl or optionally subst. C ₂ -C ₆ alkynyl and
b) if U stands for a direct bond, a group E-, E-CH ₂ -CH ₂ -, E-CH = CH-, EC∼C-, ES-, ES-CH ₂ -, E-CH ₂ - ON = CH (R ^a ) -, EC (= O) -O-CH ₂ -, EC (CH ₃ ) = NN = C (CH ₃ ) -O-CH ₂ - or R ^e R ^f N-CH ₂ - , in which
R ^e , R ^f independently of one another for radicals R ⁴ or together for heterocyclic or heteroaryl bonded via nitrogen.

The invention also relates to processes and intermediates for the preparation of these compounds and their use for Control of animal pests and harmful fungi.

Isoxazolones and triazolones ortho to the amide Carbonyl group an ortho substituted phenyl ring tra genes are known from WO-A 95/14009, WO-A 96/17851, WO-A 96/26191, WO-A 96/36229, WO-A 96/36615, WO-A 96/36616, WO-A 96/38425, WO-A 97/00612, WO-A 97/05120 and WO-A 98/20003 are known. Cyclic Amides which are ortho to the amide carbonyl group substituted heterocycle are open in WO-A 96/36633 beard.

Meta-substituted (het) aryl compounds are from WO-A 96/35669 known.

The verb described in the above scriptures are plant protection products against harmful fungi and z. T. suitable against animal pests.

However, their effect is unsatisfactory in many cases. Therefore, the task was based on connections with improved Find effectiveness.

Accordingly, the (hetero) aryl compounds defined at the outset I found. Processes and intermediates were also added their manufacture and compositions containing them for combating animal pests and fungi and their use in found this sense.

The compounds of formula I have one compared to the known Compounds increased effectiveness against harmful fungi and animal Pests on.

The compounds I can be obtained in various ways, it being irrelevant for the synthesis whether the heterocycle W or the grouping GU is initially built up. For better clarity, the description is therefore in the following synthesis descriptions
Q ^# for the grouping GU, or a suitable preliminary stage for it and
W ^# for the heterocycle W, or a suitable precursor used for it.

The structure of the heterocycle W is preferred at the stage in which Q ^{# is} methyl (for compounds in which U is oxymethylene) or a nucleophilically cleavable group (for compounds in which U is a direct bond).

The heterocycle W per se can be analogous to that in WO-A 95/14009 and Methods described in WO-A 96/36229 can be obtained.

For the synthesis of compounds of the formula IA

it is preferred to start from amines of the formula IIA ^# . They are, as far as R ^{B is} oxygen, with phosgene or a Phosgenäqui valent, such as di- or triphosgene, or, if R ^{B is} sulfur, with thiophosgene, to the corresponding isocyanates or thioisocyanates of the formula IIIA ^# implemented.

In the formula IIA ^# , Q ^# preferably represents methyl or a nucleophile-releasable group, such as halogen or alkyl or arylsulfonate, preferably bromine, chlorine, iodine, mesylate, tosylate or tri-flat.

1) The reaction of IIA ^# with phosgene or a phosgene equivalent, such as di- or triphosgene, is usually carried out at temperatures from -10 ° C to 250 ° C, preferably 10 ° C to 110 ° C, in an inert organic solvent possibly in the presence of a base [cf. Chem. Soc. Rev., Vol. 3, p. 209 (1974)].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, in- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, 1,1,1-trichloroethane, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, Ni triles such as acetonitrile and propionitrile, as well as dimethyl sulfoxide, Dimethylformamide and dimethylacetamide, particularly preferably tetra  hydrofuran, dimethylformamide, chlorobenzene, 1,1,1-trichloroethane and toluene. Mixtures of the solvents mentioned can also be used be used.

In general, inorganic compounds, such as alkali, come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, Potassium carbonate and calcium carbonate, as well as alkali metal hydrogen carbonates such as sodium bicarbonate, organometallic compound dungen, in particular alkali metal alkyls such as methyl lithium, butyl lithium and phenyllithium, alkyl magnesium halides such as Methylma magnesium chloride, as well as organic bases, e.g. B. tertiary Amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, Lutidine and 4-dimethylaminopyridine and bicyclic amines in Be dress. Triethylamine and pyridine are particularly preferred. The Bases are generally equimolar, in excess or given also used as a solvent.

An acid addition salt of IIA ^# , such as the hydrochloride, is preferably used in this reaction.

The starting materials are generally reacted with one another in equimolar amounts. It can be advantageous for the yield to use phosgene or the phosgene equivalent in an excess based on IIA ^# .

Isocyanates IIIA ^# are reacted with 1,1-di-C ₁ -C ₄ -alkylhydrazines of the formula IVa to give carbamates of the formula VA and, if R ^A in formula IA for halogen, C ₁ -C ₄ -alkoxy, C ₁ - C ₄ alkylthio or NR ^a R ^b is cyclized with phosgene or phosgene equivalents or thiophosgene to form triazolones of the formula VIA ^# .

2) The reaction with dialkylhydrazines usually takes place at Temperatures from -20 ° C to + 200 ° C, preferably -10 ° C to + 110 ° C in an inert organic solvent [cf. WO-A 97/02255; Synth. Commun. , Vol. 26, pp. 783-791 (1996)].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, 1,1,1-trichloroethane, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, Ni triles such as acetonitrile and propionitrile, as well as dimethyl sulfoxide, Dimethylformamide and dimethylacetamide, particularly preferably tetra hydrofuran, dimethylformamide, chlorobenzene, dichloromethane, toluene and 1,1,1-trichloroethane. Mixtures of the above can also be used Solvents are used.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IVa in an excess based on IIIA ^# .

3) The reaction with phosgene, a phosgene equivalent or thio Phosgene usually takes place at temperatures from -10 ° C to + 250 ° C, preferably + 10 ° C to + 120 ° C, in an inert orga African solvent, if necessary in the presence of a base [cf. WO-A 97/02255; J. Org. Chem. Vol. 54, p. 1048 (1989)].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, 1,1,1-trichloroethane, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, Ni triles such as acetonitrile and propionitrile, as well as dimethyl sulfoxide, Dimethylformamide and dimethylacetamide, particularly preferably tetra hydrofuran, dimethylformamide, chlorobenzene, 1,1,1-trichloroethane and toluene. Mixtures of the solvents mentioned can also be used be used.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium metal amides such as lithium amide, sodium amide and potassium amide, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka  lium carbonate and calcium carbonate as well as alkali metal hydrogen carbon nates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium umchloride as well as alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Orga are particularly preferred African amines, such as triethylamine or pyridine.

The bases are generally added in catalytic amounts sets, but they can also equimolar, in excess or given can also be used as a solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use phosgene in an excess based on VA ^# .

If R ^A in formula IA is not chlorine, the chlorine triazolones of the formula VIA ^# with compounds of the formula R ^A -H, where R ^{A is} C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b (R ^a and R ^b independently of one another are hydrogen or C ₁ -C ₄ -alkyl), or with bromination or iodination agents, to give the corresponding compounds VIA, in which R ^{A is} halogen, C ₁ -C ₄ -alkyl , C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b is implemented.

4) This reaction usually takes place at temperatures of -10 ° C to + 250 ° C, preferably + 10 ° C to + 120 ° C, in one erten organic solvents in the presence of a base [cf. WO-A 95/14009; WO-A 97/02255].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dio xan, anisole and tetrahydrofuran, 1,2-dimethoxyethane, nitriles such as  Acetonitrile and propionitrile, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dime thylsulfoxide, dimethylformamide and dimethylacetamide, especially preferably methanol, ethanol, 1,2-dimethoxyethane, tetrahydrofuran, Dimethylformamide, toluene, chlorobenzene and dimethyl sulfoxide. It Mixtures of the solvents mentioned can also be used the.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium metal amides such as lithium amide, sodium amide and potassium amide, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate as well as alkali metal hydrogen carbon nates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium umchloride as well as alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Natri are particularly preferred ummethanolat, sodium thiomethanolate, sodium ethanolate, sodium hy drid and pyridine.

The bases are generally equimolar, in excess or ge optionally used as a solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use R ^A -H in an excess based on VIA ^# .

If R ^{A is} C ₁ -C ₄ alkyl, the corresponding compounds VIA ^{# are obtained} from the carbamates VA '^# by reaction with orthoesters or amidines.

5) This reaction usually takes place at temperatures of 0 ° C to 200 ° C, preferably 50 ° C to 120 ° C, in an inert organic solvents [cf. J. Org. Chem., Vol. 43 (1978) P. 936].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, in- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, di oxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and also dimethyl sulfoxide, dimethylfor mamide and dimethylacetamide, particularly preferably dimethylformamide, Tetrahydrofuran or toluene. Mixtures of the so-called th solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the orthoester in an excess based on VA '^# .

The carbamates VA 'are obtained from the isocyanates IIIA ^# by reaction with alkylhydrazines of the formula IVa under those from Pharmazie, vol. 39, p. 301 (1984); Liebigs Ann. Chem., Pp. 407-413 (1994) and J. Org. Chem., Vol. 40, p. 1909 (1975) receive conditions known.

Compounds of formula IB

is obtained, for example, starting from phenylhydrazines or the corresponding heteroarylhydrazines of the formula IIB ^# by reacting IIB ^# with phosgene to give the isocyanates of the formula IIIB ^# under the conditions known from US Pat. No. 4,267,281.

The further synthesis steps, reaction with alkylhydrazines IVa to compound IVB ^# , are carried out analogously to Chapter 2); the cyclization to the triazolone VIB ^# takes place under the conditions described in Section 3).

The introduction of alkoxy, alkylthio or NR ^a R ^b groups in VIB ^# , and the construction of triazolone groups, in which R ^{A is} alkyl, from compounds IIIB ^# , is carried out under the sections 4) and 5 ) described conditions.

Intermediates of formula 1,

in the
Q is methyl, Hal-CH ₂ , OH or a nucleophilically removable group,
V CH ₂ or NR ^a and
Θ N = C = R ^B , NH-C (= R ^B ) -NH-NR ^C ₂ or a group A, where Q is not OH, if Θ N = C = R ^B are new.

For the synthesis of compounds of the formula IC

one goes preferably from (hetero) arylpropionic esters of the formula IIC ^# , in which Q for methyl or a nucleophilically cleavable group and R 'for C ₁ -C ₆ alkyl or optionally subst. Phenyl is out. They are converted with formic acid orthoesters or chloroformic acid star of formula IVb to malonic acid ester of formula IIIC ^# .

6) In the formula IIC ^# , Q ^{# is} preferably methyl or a nucleophilically cleavable group, such as halogen or alkyl or aryl sulfonate, preferably bromine, chlorine, iodine, mesylate, tosylate or triflate. In the formula IVb, R 'is C ₁ -C ₆ alkyl or optionally subst. Phenyl and R '' for chlorine, C ₁ -C ₆ alkoxy or optionally subst. Phenoxy. This reaction is carried out analogously to WO-A 95/14009 and WO-A 97/02255.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IVb in an excess based on IIC ^# .

The starting compounds IIC are commercially available or can be prepared analogously to the literature cited.

Alternatively, compounds of the formula IIIC ^{# can} also be obtained from benzyl halides or the corresponding heteroaryl halides, of the formula IIC '^#, by reaction with malonic esters of the formula IVc under basic conditions [cf. J. Org. Chem., Vol. 52, p 1381-1396 (1987); ibid., Vol. 55, pp. 247-250 (1990); WO-A 96/36229].

The malonic ester derivatives of the formula IIIC ^# are cyclized with N-hydroxy-alkylamines of the formula IVd to form isoxazolones of the formula VC ^# . In the formulas, R 'stands for C ₁ -C ₄ alkyl or optionally subst. Phenyl.

7) This reaction usually takes place at temperatures of -10 ° C to 250 ° C, preferably 10 ° C to 120 ° C, in an inert organic solvents in the presence of a base [cf. WO-A 95/14009; WO-A 97/02255].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, di oxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dime thylsulfoxide, dimethylformamide and dimethylacetamide, especially preferably methanol, tetrahydrofuran or dimethylformamide. It Mixtures of the solvents mentioned can also be used the.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium metal amides such as lithium amide, sodium amide and potassium amide, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate as well as alkali metal hydrogen carbon nates such as sodium hydrogen carbonate, organometallic compounds,  in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium umchloride as well as alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Natri are particularly preferred umhydroxid or potassium hydroxide.

The bases are generally added in catalytic amounts sets, but they can also equimolar, in excess or given can also be used as a solvent.

N-Hydroxyalkylamines of the formula IVd are commercially available.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IVd in an excess based on IIIC ^# .

Compounds of the formula VIC ^# in which R ^{A is} halogen are accessible from the isoxazolones of the formula VC ^# by reaction with halogenating agents [HAL], if appropriate in the presence of a base. Examples of suitable halogenating agents are thionyl chloride, phosphorus pentchloride, phosphorus oxychloride, phosphoryl bromide or phosphorus tribromide.

Compounds of the formula VIC ^# in which R ^{A is} C ₁ -C ₄ alkoxy are accessible from the isoxazolones of the formula VC ^# by reaction with alkylating agents, if appropriate in the presence of a base. Examples of suitable alkylating agents are alkyl halides, dialkyl sulfates, trialkyloxonium salts or trimethylsilyldiazomethane, in particular methyl iodide, dimethyl sulfate or trimethylsilyldi azomethane.

In the above formula VIC ^# , R "stands for C ₁ -C ₄ alkyl.

Compounds of the formula IC in which R ^{A is} alkyl are synthesized from compounds IIC ^# analogously to the route known from US Pat. No. 4,952,573.

For the synthesis of the compounds of the formula ID

one prefers the anilines or heteroarylamines Formula IID and sets IID with malonic acid derivatives of the formula IVc 'to the corresponding dicarbonyl compounds of the formula IIID around.

In formula IVc ', Hal represents a halogen atom, in particular bromine, and R' represents C ₁ -C ₄ alkyl or optionally subst. Phenyl.

8) This reaction takes place in the presence of a base, possibly in egg an inert organic solvent [cf. Ber. German Chem. Ges., Vol. 35, pp. 512ff. (1902); US 4,421,914; Helv. Chim. Acta, vol. 73, pp. 1700ff. (1990); WO-A 36/36229].  

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dio xan, anisole and tetrahydrofuran, nitriles such as acetonitrile and pro pionitrile, alcohols such as methanol, ethanol, n-propanol, isopropa nol, n-butanol and tert-butanol as well as dimethyl sulfoxide, dime thylformamide and dimethylacetamide, particularly preferably methanol, Tetrahydrofuran and dimethylformamide. Mixtures of mentioned solvents are used.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium metal amides such as lithium amide, sodium amide and potassium amide, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate as well as alkali metal hydrogen carbon nates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium umchloride as well as alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Organi are particularly preferred bases such as triethylamine or pyridine.

The bases are generally used in equimolar amounts, they can but also in excess or optionally as a solvent be applied.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use IID ^# in an excess based on IVc '.

The required starting materials IVc 'are commercially available.

Dicarbonyl compounds IIID ^# are cyclized with N-hydroxyalkylamines of the formula IVc to give isoxazolones of the formula IVD ^# .

9) This implementation takes place under the description in Section 7) conditions.

The introduction of the various radicals R ^A in connection with IVD ^# follows the conditions described in chapters 4) and 5).

If R ^A in formula ID does not stand for OH, IVD ^# is subjected to the implementations described in section 4) for the introduction of other radicals R ^A. If R ^A in formula ID is alkyl, the isoxazolone is built up under the conditions described in Chapter 5) for the construction of the triazolone [cf. WO-A 97/02255; J. Org. Chem., Vol. 43, p. 936 (1978)].

The synthesis of compounds of the formula IE

is preferably carried out starting from the phenols or the corresponding hetaryl alcohols of the formula IIE ^# under the conditions described in chapters 8) and 9) for the synthesis of the compounds IIID and IVD.

The introduction of the different radicals R ^A into the compounds IVE ^# , or the construction of isoxazolones in which R ^A stands for alkyl, is carried out analogously to the reactions described for the compounds VA and VIA in chapters 4) and 5).

The synthesis of compounds of formula IF

is preferably carried out starting from the thiophenols or the corresponding thioalcohols of the formula IIF ^# under the conditions described in chapters 8) and 9) for the synthesis of the compounds IC.

The introduction of the various radicals R ^A into the compounds IVF ^# , or the construction of isoxazolones in which R ^{A is} alkyl, is carried out analogously to the reactions described for the compounds VA and VIA in chapters 4) and 5).

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coals Hydrogen such as toluene, o-, m- and p-xylene, halogenated carbons hydrogen such as methylene chloride, chloroform and chlorobenzene, Ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n- Propanol, isopropanol, n-butanol and tert-butanol as well Dimethyl sulfoxide and dimethylformamide, particularly preferred Diethyl ester, tetrahydrofuran, dimethyl sulfoxide and dimethyl form  amid. Mixtures of the solvents mentioned can also be used be used.

As bases generally come inorganic compounds, e.g. B. Alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, Sodium hydroxide, potassium hydroxide, calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, Calcium oxide and sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, Alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate and alkali metal bicarbonates such as Sodium bicarbonate, organometallic compounds, ins special alkali metal alkyls such as methyl lithium, butyllithium and Phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Bases, e.g. B. tertiary amines such as trimethylamine, triethylamine, Diisopropylethylamine and N-methylpiperidine, pyridine, substi acted pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well as bicyclic amines. Be particularly preferred Sodium methoxide, potassium t-butoxide, sodium hydride, potassium carbonate and n-butyllithium. The bases are generally in equimolar amounts used, but they can also in excess or optionally used as a solvent.

The synthesis of compounds of the formula IG

preferably starts from carboxylic acid halides of the formula IIG ^# . They are converted to compounds IITG ^# with malonic acid esters IVc.

IIIG ^# is cyclized with hydroxylamines of the formula IVc analogously to the conditions described in chapter 9) to give the isoxazolones of the formula IVG ^# . The various groups R ^A are introduced under the conditions described in Sections 4) and 5).

The reaction of the carboxylic acid halides IIG ^# with the malonic esters of the formula IVc is usually carried out in an inert organic solvent, such as preferably tetrahydrofuran or toluene, in the presence of a base, such as sodium hydride or triethylamine, and optionally a Lewis acid, such as MgCl ₂ [see. J. Org. Chem., Vol. 50, p. 2622 (1985); Tetrahedron, Vol. 48 (42), pp. 9233 to 9236 (1992)].

The reaction with hydroxylamines IVd takes place under those in Ab Section 9) described conditions.

The synthesis of compounds of the formula IH

is preferably carried out by reacting the compounds of the formula IG by reaction with phosphorus compounds of the formula VIIIc in Meaning of a Wittig or a Wittig-Horner reaction among all common conditions.

The phosphorus compounds of the formula VIIIc are prepared under generally known conditions from the corresponding halides of the formula VIIIc '[(R ^a ) ₂ -CH-Hal] by reaction with phosphines, in particular triphenylphosphine, or with phosphites, trialkylphosphites being preferred [cf. . Houben-Weyl, 4th ed., Vol. XII / 1, p. 79 f. and p. 433 f. (1963)].

Intermediates of formula 3,

in the
Q 'is methyl, Hal-CH ₂ , OH or a nucleophilically removable group,
V -CH ₂ -, -C (= O) -, -C (= C [R ^a ] ₂ ) -, oxygen, sulfur, or NR ^a ,
R 'C ₁ -C ₆ alkyl or optionally subst. Phenyl means are new.

The structure of the different groups GU is described in the following synthesis descriptions. These descriptions apply to all meanings of V; the descriptions apply equally to compounds in which W ^# represents group A or B or a precursor thereof, provided that it is inert under the respective reaction conditions.

If in compounds IR ^B stands for sulfur, sulfurization is preferably carried out at the stage of the compounds VI ^# .

10) The sulfurization of VI ^# takes place under conditions known per se, it is usually carried out at temperatures from 0 ° C. to 180 ° C., preferably 20 ° C. to 140 ° C., in an inert organic solvent [cf. Liebigs Ann. Chem., P. 177 (1989)].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, di oxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and  Propionitrile, as well as dimethyl sulfoxide, particularly preferably toluene and tetrahydrofuran. Mixtures of the mentioned Lö be used.

Phosphorus pentasul, for example, come as sulfurizing agents fid or Lawesson's reagent.

The structure of the different groups GU is described in the following synthesis descriptions. These descriptions apply to all meanings of V; the descriptions apply equally to compounds in which W ^# represents group A or B or a precursor thereof, provided that it is inert under the respective reaction conditions.

If Q ^# in the formulas VI ^{# is} methyl, VI ^# is converted into compounds VII ^# by halogenation.

11) The compounds VII ^# are accessible under generally customary conditions from the corresponding methyl compounds VI ^# . The halogenation is usually carried out at temperatures from 0 ° C. to 200 ° C., preferably 20 ° C. to 110 ° C., in an inert organic solvent in the presence of a radical initiator (e.g. dibenzoyl peroxide or azobisisobutyronitrile or under UV radiation, e.g. with a mercury vapor lamp) or an acid [cf. Synthetic Reagents, Vol. 2, pp. 1-63, Verlag Wiley, New York (1974)].

The reactants are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the halogenating agent in an excess based on VI ^# .

For example, elementary halogens (e.g. Cl ₂ , Br ₂ , I ₂ ), N-bromo-succinimide, N-chlorosuccinimide or dibromodimethylhydrantoin are used as halogenating agents. The halogenating agents are generally used in equimolar amounts, in excess or, if appropriate, as a solvent.

In general, compounds I in which the group GU is bonded via carbon are preferably obtained from the halides of the formula VII ^# . By reacting VII ^# with nucleophiles before adding N, O or S nucleophiles of the formula VIII, e.g. B. with alcohols, carboxylic acids, thiols, oximes or amines leads to the corresponding ethers, esters, thioethers, oxime ethers or amines of the formula I in which the group GU for D-OCH ₂ , EC (R ² ) = N- OCH ₂ , R ⁴ ON = C (R ³ ) -C (R ² ) = N-OCH ₂ , R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N -OCH ₂ , E-SCH ₂ , E-CH ₂ -ON-CH ₂ , EC (= O) -O-CH ₂ , EC (CH ₃ ) = NN = C (CH ₃ ) -O-CH ₂ or R ^e R ^f N-CH ₂ is.

In the formulas, U * stands for oxygen, sulfur or nitrogen and G *, if U * means oxygen or sulfur, for groups D, E, R ⁴ ON = C (R ³ ) -C (R ² ) = N, E- CH ₂ -ON, EC (= O), EC (CH ₃ ) = NN = C (CH ₃ ), R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N or, if U * is nitrogen, for residues R ^e and R ^f .

12) This reaction usually takes place at temperatures of 0 ° C to 80 ° C, preferably 20 ° C to 60 ° C in an inert Solvent in the presence of a base using standard procedures [see. Organikum, 17th ed. P. 172 f (1988)].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coals Hydrogen such as toluene, o-, m- and p-xylene, halogenated carbons hydrogen such as methylene chloride, chloroform and chlorobenzene, Ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, as well as dimethyl sulfoxide and dimethyl formamide, particularly preferably methylene chloride, toluene, acetone, Acetonitrile and dimethylformamide. Mixtures of the ge named solvents can be used.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides (e.g. lithium hydroxide, Sodium hydroxide, potassium hydroxide and calcium hydroxide) alkali metal and alkaline earth metal oxides (e.g. lithium oxide, sodium oxide, Calcium oxide and magnesium oxide), silver oxide, alkali metal and Alkaline earth metal hydrides (e.g. lithium hydride, sodium hydride, Potassium hydride and calcium hydride), alkali metal amides (e.g. lithium amide, sodium amide and potassium amide), alkali metal and alkaline earth metal carbonates (e.g. lithium carbonate and calcium carbonate) and Alkali metal bicarbonates (e.g. sodium bicarbonate), organometallic compounds, especially alkali metal alkyls (e.g. like methyl lithium, butyllithium and phenyllithium), alkyl  magnesium halides (e.g. methyl magnesium chloride) and alkali metal and alkaline earth metal alcoholates (e.g. sodium methoxide, Sodium ethanolate, potassium ethanolate, potassium tert-butoxide and Dimethoxymagnesium), also organic bases, e.g. B. tertiary Amines such as trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, Lutidine and 4-dimethylaminopyridine and bicyclic amines in Be dress. Sodium hydroxide and potassium are particularly preferred carbonate and potassium tert-butanolate. The bases are generally my equimolar, in excess or possibly as a solution medium used.

It may be advantageous to implement a catalytic one Amount of a crown ether (e.g. 18-crown-6 or 15-crown-5) or Add 0.01 to 10 wt .-% potassium iodide as a catalyst.

The implementation can also consist of a two-phase system Solution of alkali or alkaline earth metal hydroxides or carbonates in Water and an organic phase (e.g. aromatic and / or halogenated hydrocarbons). As phases Transfer catalysts come here, for example, ammonium halo genides and tetrafluoroborates (e.g. benzyltriethylammonium chloride, benzyltributylammonium bromide, tetrabutylammonium chloride, Hexadecyltrimethylammonium bromide or tetrabutylammonium tetra fluoroborate) and phosphonium halides (e.g. tetrabutylphospho nium chloride and tetraphenylphosphonium bromide) into consideration.

It may be advantageous for the reaction to first react G * -N * H with the base into the corresponding anion, which is then reacted with VII ^# .

Compounds I ^# in which U stands for oxymethylene are obtained before given from compounds VII ^# by reaction with alcohols or oximes of the formula VIIIa.

In formula VIIIa, G represents a group D, E- (R ² ) C = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N or R ⁴ ON = C (R ³ ) -C ( = N-OR ⁴ ) -C (R ² ) = N. The radicals D, E, R ² , R ³ and R ⁴ have the meaning given in claim 1.

13) This implementation takes place under the in the previous chapter described conditions, usually at temperatures of 0 ° C to 180 ° C, preferably 20 ° C to 60 ° C, in an inert organic solvents in the presence of a base [cf. EP-A 254 426; EP-A 463 488; WO-A 95 / 18,789; WO-A 95 / 29,896].

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, in- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, di oxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, as well as dime thylsulfoxide, dimethylformamide and dimethylacetamide, especially preferably dimethylformamide, tetrahydrofuran and acetone. It can mixtures of the solvents mentioned can also be used.

In general, inorganic compounds, such as alkali, come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate, as well as alkali metal hydrogen car Bonate such as sodium bicarbonate, organometallic compounds gene, especially alkali metal alkyls such as methyl lithium, butylli thium and phenyllithium, alkyl magnesium halides such as methylma magnesium chloride, and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Natri are particularly preferred umhydrid, potassium carbonate and sodium methoxide. The bases will be generally equimolar, in excess or optionally as Solvent used.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use G-OH in an excess based on VII ^# .

The output required for the preparation of compounds I ' substances G-OH are known or can according to the litera cited be manufactured.

Compounds of the formula I ^# , in which GU represents R ^e R ^f N-CH ₂ , are obtained from compounds VII ^# by reaction with amines or cyclic compounds of the formula VIIId under conditions known from the literature. In formula VIIId, R ^a and R ^{b have} the meaning given in claim 1.

14) This implementation is usually carried out under the in Chapter 11) outlined conditions [cf. also Houben-Weyl, methods of Organic Chemistry, Vol. XI / 1, Georg Thieme Verlag Stutt cooked in 1957; Synth. Commun. 1989, p. 1309; Tetrahedron Lett 1985, p. 421; J. Med. Chem. 1985, p. 1468; J. Med. Chem. 1984, P. 1452; Ann. Chem. 1983, p. 1078].

Compounds of the formula I in which GU represents a group E are preferred from the compounds of the formula VI ^# in which Q ^{# represents} a nucleophilically removable group L, such as halogen (e.g. chlorine, bromine and iodine, in particular bromine ) or alkyl or aryl sulfonate (e.g. methyl sulfonate, trifluoromethyl sulfonate, phenyl sulfonate and 4-methylphenyl sulfonate) is obtained by reaction with organometallic compounds of the formula VIIIb.

In formula VIIIb, M represents a group Mg-Hal, Zn-Hal or B (OR ^a ) ₂ , where Hal is a halogen atom and R ^{a is} hydrogen or C ₁ -C ₄ -alkyl. Compounds VIIIb are preferably used in which M is B (OH) ₂ .

15) This reaction usually takes place at temperatures of -10 ° C to 250 ° C, preferably + 10 ° C to 120 ° C, in the presence a base and a transition metal catalyst in one in erten organic solvents [cf. DE-A 196 36 995; Acta. Chem. Scand., Vol. 47, p. 221 (1993)].  

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coal water materials such as toluene, o-, m- and p-xylene, halogenated coal water substances such as methylene chloride, chloroform and chlorobenzene, ether such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dio xan, anisole and tetrahydrofuran, ethylene glycol dimethyl ether, Ni trile such as acetonitrile and propionitrile, ketones such as acetone, methy ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol as well as dimethyl sulfoxide, dimethylformamide and dime thylacetamide, particularly preferably ethylene glycol dimethyl ether or Ethylene glycol dimethyl ether / water mixture. Gemi cal of the solvents mentioned are used.

In general, inorganic compounds such as alkali come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium metal amides such as lithium amide, sodium amide and potassium amide, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate as well as alkali metal hydrogen carbon nates such as sodium hydrogen carbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium umchloride as well as alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Sodium is particularly preferred carbonate.

The bases are generally added in catalytic amounts sets, but they can also equimolar, in excess or given can also be used as a solvent.

As transition metal catalysts are iron, cobalt, nickel, Rhodium, platinum or palladium compounds, especially Nickel (0), nickel (II) palladium (0) and palladium (II) verbin suitable. Salts such as palladium chloride or Palladium acetate or Pd complexes can be used. Advance is only that the ligands on the palladium under the reac conditions can be displaced from the substrate.  

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use VIIIb in an excess based on VI ^# .

The starting compounds VIIIb, in which M is B (OH) ₂ , are known from the literature or can be obtained according to the known methods [cf. Chem. Rev. 1956, p. 959; H. & McCloskey AL (ed.), Progress in Boron Chemistry 1964, p.369; Houben-Weyl, Methods of Organic Chemistry, Vol. 13 / 3a, 4th edition, pp. 617ff., Georg Thieme Verlag Stuttgart 1982; Org. Syntheses, Coll. Vol. 4, p. 68; Org. Syntheses, Coll. Vol. 5, p. 918; Chem. Ber. 1990, p. 1841].

Compounds of the formula I in which GU represents a group EC∼C are preferred from the compounds of the formula VI ^# in which Q ^{# represents} halogen (in particular bromine or iodine) by reaction with acetylene derivatives of the formula VIIIe in the sense received a Heck reaction.

16) This implementation takes place under known conditions [cf. JP-A 58/121242; Tetrahedron Lett., Vol. 28, pp. 5981ff (1987); J. Organomet. Chem., Vol. 93, p. 259 (1975)] in the presence a transition metal catalyst [TM] as in the above Chapter described, e.g. B. a palladium or nickel compound such as diacetyl palladium, palladium dichloride, palladium terta (triphenylphosphine) or nickel dichloride, in one th solvent (e.g. dimethylformamide, acetonitrile, tetra hydrofuran or toluene) and in the presence of a base (e.g. Potassium carbonate, sodium hydride, diethylamine, triethylamine or Pyridine).

In a further embodiment of the process according to the invention, compounds of the formula I in which GU represents a group EC∼C can also be obtained from the corresponding aldehydes of the formula IX ^# , IX ^# first by reaction with phosphorus compounds of the formula VIIIf in the sense a Wittig reaction are converted into the olefins of the formula X ^# , which are converted under basic conditions with elimination of HCl to the acetylenes of the formula Xa ^# . The acetylenes of the formula Xa ^# are converted with compounds of the formula VIIIg into the compounds of the formula I ^# in which GU represents a group EC∼C [cf. Chem. Commun., P. 446 (1978); Tetrahedron Lett., Vol. 21, p. 4021 (1980); ibid., vol. 27, p. 5853 (1986); J. Chem. Res. (S), p. 106 (1978); ibid. (S), p. 190 (1979); ibid. (S), p. 270 (1981); Chem. Lett., P. 669 (1980) Tetrahedron Lett., Vol. 27, p. 5445 (1986)].

Compounds of the formula I in which GU represents a group E-CH = CH are preferably obtained from the compounds of the formula VII ^# by oxidation to the corresponding aldehydes and subsequent Wit tig or Wittig-Horner reaction with phosphorus compounds of the formula VIIIf ' .

In formula VIIIf 'stands for a phosphoranyl residue, as in for example triphenylphosphoranyl.

20) The phosphorus compounds of formula VIIIf 'are according to a Wittig or Wittig-Horner reaction at temperatures from -30 ° C to 60 ° C, preferably 0 ° C to 40 ° C in an inert solvent in the presence of a base with the aldehyde Formula IX ^# implemented.

Suitable solvents are aliphatic hydrocarbons such as Pentane, hexane, cyclohexane and petroleum ether, aromatic coals Hydrogen such as toluene, o-, in- and p-xylene, halogenated carbons hydrogen such as methylene chloride, chloroform and chlorobenzene, Ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, Dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and Propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n- Propanol, isopropanol, n-butanol and tert-butanol as well Dimethyl sulfoxide and dimethylformamide, particularly preferred Diethyl ester, tetrahydrofuran, dimethyl sulfoxide and dimethyl form  amid. Mixtures of the solvents mentioned can also be used be used.

As bases generally come inorganic compounds, e.g. B. Alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, Sodium hydroxide, potassium hydroxide, calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, Calcium oxide and sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, Alkali metal and alkaline earth metal carbonates such as lithium carbonate and calcium carbonate and alkali metal bicarbonates such as Sodium bicarbonate, organometallic compounds, ins special alkali metal alkyls such as methyl lithium, butyllithium and Phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alcoholates such as Sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Bases, e.g. B. tertiary amines such as trimethylamine, triethylamine, Diisopropylethylamine and N-methylpiperidine, pyridine, substi acted pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well as bicyclic amines. Be particularly preferred Sodium methoxide, potassium t-butoxide, sodium hydride, potassium carbonate and n-butyllithium. The bases are generally in equimolar amounts used, but they can also in excess or optionally used as a solvent.

The starting materials IX ^# and VIIIf 'are generally reacted with one another in equimolar amounts. It can be advantageous for the yield to use one of the components in excess.

The phosphorus compounds of the formula VIIIf 'are, under generally known conditions, from the corresponding halides of the formula VIIIf''(E-CH ₂ -Hal) by reaction with phosphines, in particular triphenylphosphine, or with phosphites, trialkyl phosphites being preferred [cf. Houben-Weyl, 4th ed., Vol. XII / 1, p. 79 f. and p. 433 f. (1963)].

In a modification of the above process, the compounds of the formula I in which GU stands for a group E-CH = CH are also obtained by first oxidizing the halide VIIIf "to the corresponding aldehyde VIIIh and then VIIIh with a phosphorus compound X ^# implemented in the sense of a Wittig or Wittig-Horner reaction.

The oxidation of the halide VIIIf '' to the aldehyde VIIIh takes place under the conditions described in Chapter 17). As an oxide tion agents [OX] serve, for example, methylmorpholine-N-oxide mo  nohydrate (cf. EP-A 393 428) or dimethyl sulfoxide [cf. J. Chem. Soc. 1964, p. 520; J. Org. Chem. 24, 1792 (1959)].

The phosphorus compounds of the formula X ^# are produced under the conditions described above from the halides VII ^# . The oxidation of VIIIf '' to VIIIh and the subsequent Wittig or Wittig-Horner reaction also take place according to the conditions described above.

Compounds of the formula I in which U is oxygen and G is a group D are obtained by reacting the phenols or the corresponding heteroaryl alcohols of the formula X ^# with compounds of the formula VIIIg '. In formula VIIIg 'L stands for usual leaving groups, such as halogen or alkyl or aryl sulfonate, preferably bromine, chlorine, iodine, mesylate, tosylate or triflate.

21) This reaction usually takes place at temperatures of -20 ° C to 180 ° C, preferably 20 ° C to 160 ° C, in an inert organic solvents in the presence of a base [cf. EP-A 203 608; EP-A 242 081].

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 methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, Ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-Bu tylmethyl ketone, as well as dimethyl sulfoxide, dimethylformamide and di methylacetamide, particularly preferably dimethylformamide and dime ethyl sulfoxide. Mixtures of the solvents mentioned can also be used be used.  

In general, inorganic compounds, such as alkali, come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Al potassium and alkaline earth metal carbonates such as lithium carbonate, Ka lium carbonate and calcium carbonate, as well as alkali metal hydrogen car Bonate such as sodium bicarbonate, organometallic compounds gene, especially alkali metal alkyls such as methyl lithium, butylli thium and phenyllithium, alkyl magnesium halides such as methylma magnesium chloride and alkali metal and alkaline earth metal alcoholates such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butanolate and dimethoxymagnesium, also organic Ba sen, e.g. B. tertiary amines such as trimethylamine, triethylamine, tri isopropylethylamine and N-methylpiperidine, pyridine Pyridines such as collidine, lutidine and 4-dimethylaminopyridine as well bicyclic amines. Natri are particularly preferred umhydrid, potassium tert-butanolate and potassium carbonate. The bases are generally equimolar, in excess or, if appropriate used as a solvent.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use VIIIg 'in an excess based on X ^# .

The required starting materials VIIIg 'are in the literature knows or can be made according to the literature cited the.

Compounds of formula I in which U for oxygen and G for EC (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N, R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N or a group D is preferably obtained by connecting compounds of the formula VI ^# in which Q ^{# is} halogen (in particular bromine or iodine) Implementation with compounds of the formula VIIIa *. In the formulas, G * stands for EC (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N or R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N or a group D.

22) This reaction usually takes place at temperatures of -20 ° C to 170 ° C, preferably 0 ° C to 100 ° C, in an inert organic solvents in the presence of a base and possibly  a catalyst [cf. WO-A 97/24317; J. Chem. Soc. Perkin Trans., Vol. 1, p. 1727 (1989); J. Am. Chem. Soc., Vol. 119, P. 10539f. (1997)].

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 methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, Ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-Bu tylmethyl ketone, as well as dimethyl sulfoxide, dimethylformamide and di methylacetamide, toluene is particularly preferred. It can too Mixtures of the solvents mentioned are used.

In general, inorganic compounds, such as alkali, come as bases metal and alkaline earth metal hydroxides such as lithium hydroxide, natri Umhydroxid, potassium hydroxide and calcium hydroxide, alkali metal and Alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as Lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal and alkaline earth metal carbonates such as lithium carbonate, Potassium carbonate, calcium carbonate and cesium carbonate, as well as alkali metal bicarbonates such as sodium bicarbonate, metallorga African compounds, especially alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium, alkyl magnesium halides such as methyl magnesium chloride, as well as alkali metal and alkaline earths tall alcoholates such as sodium methoxide, sodium ethoxide, potassium thanolate, potassium tert-butoxide and dimethoxy magnesium, except the organic bases, e.g. B. tertiary amines such as trimethylamine, Triethylamine, tri-isopropylethylamine and N-methylpiperidine, Pyri din, substituted pyridines such as collidine, lutidine and 4-dimethyl aminopyridine and bicyclic amines. Especially be cesium carbonate is preferred. The bases are generally equimolar, in excess or optionally as a solvent used.

The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use VIIIa * in excess based on VI ^# .

The starting materials of the formula VIIIa * are in the literature knows, e.g. T. commercially available or can according to the cite literature are produced.

If individual compounds I are not on the above written ways are accessible through derivatization tion of other compounds I are prepared.  

The reaction mixtures are worked up in a conventional manner, e.g. B. by mixing with water, separation of the phases and given if chromatographic purification of the raw products. The intermediate and end products fall e.g. T. in the form of colorless or slightly brown Licher, viscous oils that are under reduced pressure and at moderate at elevated temperatures freed of volatile components or cleaned be inclined. If the intermediate and end products as solids cleaning can also be obtained by recrystallization or digesting.

The compounds I can be produced due to their C = C- and C = N double bonds are obtained as E / Z isomer mixtures which e.g. B. by crystallization or chromatography in the usual way can be separated into the individual connections.

If isomeric mixtures are obtained in the synthesis, in general However, a separation is not absolutely necessary, because the individual isomers partially during the preparation for the Application or during application (e.g. under light, acid or Base action) can convert into each other. Corresponding order Changes can also be made after application, for example during the Treatment of plants in the treated plant or in be fighting harmful fungus or animal pest.

With regard to the R ⁴ ON = C (R ³ ) -C (R ² ) = NO double bonds, the cis isomers of the compounds I (configuration based on the radical R ² in relation to the = NO Group or based on the radical R ³ in relation to the -N = OR ⁴ group) is preferred.

With regard to the E-CH = CH double bonds in compounds I who which the E isomers prefer.

In the definitions of the symbols given in the formulas above, collective terms were used which generally represent the following substituents:
Halogen: fluorine, chlorine, bromine and iodine;
Alkyl: saturated, straight-chain or branched hydrocarbon residues with 1 to 4 or 6 carbon atoms, e.g. B. C ₁ -C ₆ alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3rd -Methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbu tyl, 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;
Haloalkyl: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms (as mentioned above), in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, e.g. B. C ₁ -C ₂ haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2.2 -Di fluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Alkoxy: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the skeleton via an oxygen atom (-O-);
Haloalkoxy: straight-chain or branched haloalkyl groups with 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the structure via an oxygen atom (-O-);
Alkylthio: straight-chain or branched alkyl groups with 1 to 4 or 6 carbon atoms (as mentioned above) which are bonded to the structure via a sulfur atom (-S-);
Haloalkylthio: straight-chain or branched haloalkyl groups with 1 to 4 or 6 carbon atoms (as mentioned above), which are bonded to the skeleton via a sulfur atom (-S-);
Alkylsulfonyl: a straight-chain or branched alkyl group with 1 to 4 or 6 carbon atoms (as mentioned above) which is bonded to the skeleton via a sulfonyl group (-SO ₂ -);
Alkenyl: unsaturated, straight-chain or branched hydrocarbon radicals with 2 to 6 carbon atoms and a double bond in any position, e.g. B. C ₂ -C ₆ alkenyl 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-1-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 yl- 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;
Alkynyl: straight-chain or branched hydrocarbon groups with 2 to 6 carbon atoms and a triple bond in any position, e.g. B. C ₂ -C ₆ alkynyl 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, 1st , 1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1st -Ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Cycloalkyl: monocyclic, saturated hydrocarbon groups with 3 to 6 carbon ring members, e.g. B. C ₃ -C ₈ cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl;
Saturated or partially unsaturated cyclic radical, which in addition to carbon atoms as ring members may contain heteroatoms from the group consisting of oxygen, sulfur or nitrogen: cycloalkyl having 3 to 12 carbon ring members as mentioned above or containing 5- or 6-membered heterocycles (heterocyclyl) in addition to carbon ring members up to three nitrogen atoms and / or one oxygen or sulfur atom or one or two oxygen and / or sulfur atoms, e.g. B. 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiaziazinyl Isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazo lidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1, 2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazoli din-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-thia diazolidin-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-isoxazoline-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4 -Isoxazolin-4-yl, 2-isox azolin-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-dihydropyrazole- 1-yl, 2,3-dihydropyrazole-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazole -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-di hydrooxazol-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-tetrahydro pyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyri dazinyl, 2-hexahydropyrimidinyl, 4-He xahydropyrimidinyl, 5-Hexahydropyrimidinyl, 2-Piperazinyl, 1,3,5-Hexahydro-triazin-2-yl and 1,2,4-Hexahydrotriazin-3-yl;
Aryl: a mono- to trinuclear aromatic ring system containing 6 to 14 carbon ring members, e.g. B. phenyl, naphthyl and anthracenyl;
Arylsulfonyl: a mono- to trinuclear aromatic ring system (as mentioned above) which is bonded to the skeleton via a sulfonyl group (-SO ₂ -);
aromatic ring system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen: aryl as mentioned above or one or two nuclear heteroaryl, e.g. B.

• - 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or Oxygen atom: 5-ring heteroaryl groups, which in addition to carbon Substance atoms one to four nitrogen atoms or one to three Nitrogen atoms and a sulfur or oxygen atom as a ring may contain members, for. B. 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-oxadia zol-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;
• - Benzo-condensed 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one acid Substance or sulfur atom: 5-ring heteroaryl groups, which ne ben carbon atoms one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as Ring members can contain, and in which two adjacent Carbon ring members or one nitrogen and one neighboring carbon ring member through a buta-1,3-diene-1,4- diyl group can be bridged;
• - Containing 5-membered heteroaryl bound via nitrogen one to four nitrogen atoms, or nitrogen bound benzo-fused 5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups, which next to Carbon atoms one to four nitrogen atoms or one to can contain three nitrogen atoms as ring members, and in which two adjacent carbon ring links or a stick fabric and an adjacent carbon ring member by a Buta-1,3-diene-1,4-diyl group can be bridged, this Tied rings over one of the nitrogen ring links to the frame are;
• - 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups, which next to Carbon atoms one to three or one to four nitrogen may contain atoms as ring members, for. B. 2-pyridinyl, 3-py ridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyri midinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5- Triazin-2-yl and 1,2,4-triazin-3-yl;

Alkylene: divalent unbranched chains from 3 to 5 CH ₂ groups, e.g. B. CH ₂ , CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ , CH ₂ CH ₂ CH ₂ CH ₂ and CH ₂ CH ₂ CH ₂ CH ₂ CH ₂ ;

organic rest: if necessary subst. Alkyl, alkenyl, alkynyl, cyclo alkyl, heterocyclyl, aryl or hetaryl.

The addition "possibly subst." with respect to alkyl, alkenyl and alkynyl groups is intended to express that these groups can be partially or completely halogenated [ie the hydrogen atoms of these groups can be partially or completely replaced by the same or different halogen atoms as mentioned above (preferably fluorine, chlorine or Bromine) can be replaced] and / or can carry one to three (preferably one) of the following radicals:

• - cyano, nitro, hydroxy, amino, formyl, carboxyl, aminocarbonyl, Alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylamino, Dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, Alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, Alkoxycarbonylamino, alkylcarbonyl-N-alkylamino and alkylcarbo nyl-N-alkylamino, the alkyl groups being present in these radicals preferably 1 to 6 carbon atoms, in particular 1 to 4 Contain carbon atoms;
• - Unsubstituted or substituted by usual groups Cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, Cycloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocy clylthio, heterocyclylamino or heterocyclyl-N-alkylamino where in the cyclic systems 3 to 12 ring members, preferably 2 up to 8 ring links, in particular 3 to 6 ring links included and the alkyl groups in these residues are preferably 1 to 6 Contain carbon atoms, in particular 1 to 4 carbon atoms ten;
• - Unsubstituted or substituted by usual groups Aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylal koxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, Hetaryl, hetaryloxy, hetarylthio, hetarylamino, hetaryl-N-alkyl amino, hetarylalkoxy, hetarylalkylthio, hetarylalkylamino and Hetarylalkyl-N-alkylamino, the aryl radicals preferably 6 Contain up to 10 ring members, especially 6 ring members (phenyl) ten, the hetaryl residues contain in particular 5 or 6 ring members ten and the alkyl groups in these radicals preferably 1 to 6 Contain carbon atoms, in particular 1 to 4 carbon atoms ten.

The addition "optionally subst" with respect to the cyclic (saturated, unsaturated or aromatic) groups is intended to express that these groups can be partially or completely halogenated [ie the hydrogen atoms of these groups can be partially or completely replaced by identical or different halogen atoms as mentioned above (preferably fluorine, chlorine or bromine, in particular fluorine or chlorine) can be replaced] and / or can carry one to four (in particular one to three) of the following radicals:

• - Cyano, nitro, hydroxy, amino, carboxyl, aminocarbonyl, alkyl, haloalkyl, alkenyl, haloalkenyl, alkenyloxy, haloalkenyloxy, alkynyl, haloalkynyl, alkynyloxy, haloalkynyloxy, alkoxy, halogenalkoxy, alkylthio, haloalkylthio, alkylamino, dialkylamino, carbonylylcarbonyl , Alkylcarbonyloxy, alkyl aminocarbonyl, dialkylaminocarbonyl, alkylcarbonylamino, alk oxycarbonylamino, alkylcarbonyl-N-alkylamino and alkoxycarbo nyl-N-alkylamino, the alkyl groups in these radicals preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the alkenyl mentioned - or alkynyl groups in these radicals contain 2 to 8, preferably 2 to 6, in particular 2 to 4, carbon atoms;
  and / or one to three (in particular one) of the following radicals:
• - Unsubstituted or substituted by usual groups Cycloalkyl, cycloalkoxy, cycloalkylthio, cycloalkylamino, cy cloalkyl-N-alkylamino, heterocyclyl, heterocyclyloxy, heterocy clylthio, heterocyclylamino or heterocyclyl-N-alkylamino where in the cyclic systems 3 to 12 ring members, preferably 2 up to 8 ring links, in particular 3 to 6 ring links included and the alkyl groups in these residues are preferably 1 to 6 Contain carbon atoms, in particular 1 to 4 carbon atoms ten;
• - Aryl, aryloxy, arylthio, arylamino, aryl-N-alkylamino, arylal koxy, arylalkylthio, arylalkylamino, arylalkyl-N-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino-alkylamino-hetaryl-n-aryloxy, aryloxy, hetarylthio, unsubstituted or substituted by customary groups , Hetarylalkylthio, hetarylalkylamino and hetarylalkyl-N-alkylamino, where the aryl radicals preferably contain 6 to 10 ring members, in particular 6 ring members (phenyl), the hetaryl radicals contain in particular 5 or 6 ring members and the alkyl groups in these radicals preferably contain 1 to 6 carbon atoms, in particular contain 1 to 4 carbon atoms
  and / or can carry one or two (in particular one) of the following radicals:
• - formyl,
• CR ⁱⁱⁱ = NOR ^iv [where R ^{iii is} hydrogen, alkyl, cycloalkyl and aryl and R ^{iv is} alkyl, alkenyl, haloalkenyl, alkynyl and arylalkyl (the alkyl groups mentioned preferably containing 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, said cycloalkyl groups, alkenyl groups and alkynyl groups preferably contain 3 to 8, in particular 3 to 6, carbon atoms) and aryl, in particular phenyl, which is unsubstituted or can be substituted by customary groups] or
• - NR ^v -CO-DR ^vi [where R ^{v is} hydrogen, hydroxy, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ alkoxy, C ₂ -C ₆ -alkenyloxy, C ₂ -C ₆ -alkynyloxy, C ₁ -C ₆ -alkoxy-C ₁ -C ₆ -alkyl, C ₁ -C ₆ -alkoxy- C ₁ -C ₆ -alkoxy and C ₁ - C ₆ alkoxycarbonyl, R ^{vi is} hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₆ cycloalkyl, C ₃ -C ₆ cycloalkenyl , Aryl, aryl-C ₁ -C ₆ -alkyl, hetaryl and hetaryl-C ₁ -C ₆ -alkyl and D is a direct bond, oxygen or nitrogen, where the nitrogen can carry one of the groups mentioned at R ^vi ],
  and / or in which two adjacent C atoms of the cyclic systems are C ₃ -C ₅ alkylene, C ₃ -C ₅ alkenylene, oxy-C ₂ -C ₄ alkylene, oxy-C ₁ -C ₃ -alkyleneoxy, oxy-C ₂ -C ₄ -alkenylene, oxy-C ₂ - C ₄ -alkenyleneoxy or butadienediyl group, where these bridges can in turn be partially or completely halogenated and / or an to d 99999 00070 552 001000280000000200012000285919988800040 0002019834557 00004 99880rei, especially one or two of the following residues:
• - C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo alkoxy and C ₁ -C ₄ alkylthio.

Typical groups are to be understood in particular as the following substituents: halogen, cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkyl amino, di-C ₁ -C ₄ alkylamino and C ₁ -C ₄ alkylthio.

With regard to their intended use of the connection gene of formula I are the following meanings of the substituents ten, individually or in combination, in particular preferred:

The particularly preferred embodiments of the intermediates in terms of the variables correspond to those of the radicals X, Y, Z, V, W, U, G, R ¹ , R ² , R ³ and R ^{4 of} the formula I.

Compounds of the formula Ia are particularly preferred

in which V means -CH ₂ - or -NR ^a -.

In addition, compounds of the formula Ib,

in which V -CH ₂ -, -NR ^a -, -O-, -S-, -C (= O) - or -C (= CR ^a ₂ ) - means, particularly preferred.

Compounds of the formula Ib in which V is -CH ₂ - or -NR ^a - are particularly preferred.

In particular, compounds IA are also preferred.

Compounds of the formula IB are also preferred.

Compounds of the formula IC are also particularly preferred.

In addition, compounds of the formula ID are also preferred.

Compounds ID in which R ^{a is} methyl are particularly preferred.

In addition, compounds of the formula I are particularly preferred, in where G-U stands for a group E.

Compounds of the formula I are also preferred in which U is oxygen and G is a group D, EC (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N or R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N.

In addition, compounds I are particularly preferred in which U stands for oxymethylene.

Likewise, particular preference is given to compounds I in which GU is DO-CH ₂ .

In addition, compounds I are particularly preferred in which GU is R ⁴ ON = C (R ³ ) -C (R ² ) = NO-CH ₂ .

In addition, compounds I are particularly preferred in which R ^{1 represents} hydrogen.

Likewise, particular preference is given to compounds I in which the substituent R ^{1 is not} ortho to the groups V and Z What is hydrogen.

In addition, compounds I are particularly preferred in which X, Y, and Z stand for = CH-.

Likewise, particular preference is given to compounds I in which X stands for = N- and Y and Z for = CH-.

Furthermore, compounds of the formula I in which V represents N-CH _{3 are} particularly preferred.

Furthermore, compounds I are particularly preferred in which V stands for methylene.

Likewise, particular preference is given to compounds I in which R ^{B represents} oxygen.

In addition, compounds I are particularly preferred in which R ^{A is} methoxy and R ^{C is} methyl.

In addition, compounds IA.1 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH- and D ' for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

Likewise, particular preference is given to compounds IA.2 in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z are = CH and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinoyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In addition, compounds IA.3 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH- and D ' for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In particular, compounds IA.4 are also preferred in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxa linyl, isoxazolyl or pyrazolyl.

In addition, compounds IA.5 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

Likewise, particular preference is given to compounds IA.6 in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclopropyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ alkyl, C ₃ -C _6- cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds IA.7 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxa linyl, isoxazolyl or pyrazolyl.

Furthermore, compounds IA.8 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds IA.9 are particularly preferred in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y, and Z is = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclopropyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

Equally particularly preferred are compounds IC.1, in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH- and D. 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinoyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In addition, compounds IC.2 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH- and D ' for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

Compounds IC.3 are particularly preferred in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y, and Z is = CH- and D ' for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In addition, compounds IC.4 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxa linyl, isoxazolyl or pyrazolyl.

Likewise, particular preference is given to compounds IC.5 in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds IC.6 are particularly preferred in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclopropyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ alkyl, C ₃ -C ₆ cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ ^, alkynyl.

Furthermore, compounds IC.7 are particularly preferred in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for optionally subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In addition, compounds IC.8 are particularly preferred in which R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or phenyl optionally substituted by halogen or C ₁ -C ₄ alkyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

Equally particularly preferred are compounds IC.9 in which R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclopropyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ alkyl, C ₃ -C _6- cycloalkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds ID.1 are particularly preferred in which R ^{a is} methyl, R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z is = CH- and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

Likewise, particular preference is given to compounds ID.2 in which R ^{a is} methyl, R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z. for = CH- and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazo lyl.

In addition, compounds ID.3 are particularly preferred in which R ^a for methyl, R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH- and D 'for subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

Compounds ID.4 in which R ^{a is} methyl, R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z are CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for optionally subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

In addition, compounds ID.5 are particularly preferred in which R ^a for methyl, R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or optionally substituted by halogen or C ₁ -C ₄ alkyl phenyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

Likewise, particular preference is given to compounds ID.6 in which R ^{a is} methyl, R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y and Z. for = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclopropyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ - Alkyl, C ₃ -C ₆ cyclo alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds ID.7 are particularly preferred in which R ^a for methyl, R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl, trifluoromethyl or cyclopropyl and D 'for optionally subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl.

Furthermore, compounds ID.8 are particularly preferred in which R ^{a is} methyl, R ^{A is} methoxy, ethoxy or chlorine, R ^{B is} oxygen, R ^{C is} methyl or ethyl, R ^{1 is} hydrogen, X, Y, and Z for = CH-, R ² for methyl and R ³ for C ₁ -C ₄ alkyl, methoxy, thiomethyl, cyclopropyl or optionally phenyl substituted by halogen or C ₁ -C ₄ alkyl and R ⁴ for hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds ID.9 are particularly preferred in which R ^a for methyl, R ^A for methoxy, ethoxy or chlorine, R ^B for oxygen, R ^C for methyl or ethyl, R ¹ for hydrogen, X, Y, and Z for = CH-, R ² for methyl or cyclopropyl, R ³ for methyl, ethyl, cyclo propyl or trifluoromethyl, R ⁴ for hydrogen, cyano or C ₁ -C ₃ alkyl or cyclopropyl and R ^{4 '} for C ₁ -C ₆ alkyl , C ₃ -C ₆ cyclo alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl.

In addition, compounds IA are particularly preferred in which R ^{A is} methoxy, R ^{C is} methyl, U is oxymethylene and G is substituted phenyl.

Likewise, particular preference is given to compounds IA in which R ^{A is} methoxy, R ^{C is} methyl and GU is substituted aryl.

Compounds of the formula I 'in which X, Y, Z = CR ¹ -, V methylene (-CH ₂ -), W is a group A or B, where R ^{B is} oxygen, G' is a group D ', D' -O-, D'-O-CH ₂ , D'-C (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N, R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = N, D'-CH = CH, D'-C∼C or R ^e R ^f N-CH ₂ , where D 'optionally subst. Aryl or optionally subst. Hetaryl, R ^e and R ^f together for heterocyclyl or hetero aryl bonded via nitrogen are particularly preferred.

Compounds of the formula Ia 'in which X = CH- or = N-, Y and Z = CH-, R ^{1 is} hydrogen, V -CH ₂ - or -N (CH ₃ ) -, R ^{A is} methoxy, ethoxy or chlorine, R ^B oxygen, R ^C methyl or ethyl and G 'a group D', D'-O-, D'-O-CH ₂ , D'-C (R ² ) = NO-, R ⁴ ON = C (R ³ ) -C (R ² ) = NO-, R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = NO-, D'-C (R ² ) = NO -CH ₂ , R ⁴ ON = C (R ³ ) -C (R ² ) = NO-CH ₂ or R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = NO-CH ₂ , where D 'optionally subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl and R ² and R ^{3 are} methyl or methoxy and R ^{4 is} methyl, ethyl, allyl or propargyl are particularly preferred.

Likewise, compounds of the formula Ib 'in which X = CH- or = N-, Y and Z = CH-, R ^{1 is} hydrogen, V -CH ₂ - or -N (CH ₃ ) -, R ^{A is} methoxy, ethoxy or Chlorine, R ^B oxygen, R ^C methyl or ethyl and G 'a group D', D'-O-, D'-O-CH ₂ , D'-C (R ² ) = NO-, R ⁴ ON = C (R ³ ) -C (R ² ) = NO-, R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = NO-, D'-C (R ² ) = NO-CH ₂ , R ⁴ ON = C (R ³ ) -C (R ² ) = NO-CH ₂ or R ⁴ ON = C (R ³ ) -C (= N-OR ⁴ ) -C (R ² ) = NO-CH ₂ , where D 'optionally subst. Phenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, thienyl, quinoxalinyl, isoxazolyl or pyrazolyl and R ² and R ^{3 are} methyl or methoxy and R ^{4 is} methyl, ethyl, allyl or propargyl, especially before.

In particular, with regard to their use, those shown in fol Compounds I compiled in the tables preferred. The groups in the tables for a substituent also considered individually, regardless of the combination, in of which they are called, a particularly preferred embodiment of the relevant substituents.

Table 1

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly

Table 2

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly.

Table 3

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A corresponds.

Table 4

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 5

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds.

Table 6

Compounds of the formula IA.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds.

Table 7

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly.

Table 8

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly.

Table 9

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A corresponds.

Table 10

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 11

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds.

Table 12

Compounds of the formula IA.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A corresponds.

Table 13

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly.

Table 14

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A speaks accordingly.

Table 15

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of table A corresponds.

Table 16

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 17

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds

Table 18

Compounds of the formula IA.3, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds.

Table 19

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 20

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 21

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 22

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 23

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 24

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 25

Compounds of formula IA.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 26

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 27

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 28

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 29

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 30

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 31

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 32

Compounds of formula IA.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 33

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 34

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 35

Compounds of the formula IA.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 36

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 37

Compounds of formula IA.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 38

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 39

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 40

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 41

Compounds of the formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 42

Compounds of formula IA.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 43

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 44

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 45

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 46

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 47

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 48

Compounds of the formula IA.5, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ corresponds to one row of Table B for a connection.

Table 49

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 50

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 51

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 52

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 53

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 54

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 55

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 56

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 57

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 58

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 59

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 60

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 61

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 62

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 63

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 64

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 65

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 66

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 67

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 68

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 69

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 70

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 71

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 72

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds to one row of Table C.

Table 73

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 74

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 75

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 76

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 77

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 78

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a Ver compound corresponds to one row of Table C.

Table 79

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 80

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 81

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 82

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 83

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 84

Compounds of the formula IA.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds to one row of Table C.

Table 85

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 86

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 87

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 88

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 89

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 90

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 91

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 92

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 93

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 94

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 95

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 96

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 97

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 98

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 99

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 100

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 101

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 102

Compounds of the formula IA.7, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 103

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 104

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 105

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 106

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 107

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 108

Compounds of the formula IA.8, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ corresponds to one row of Table B for a connection.

Table 109

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ⁴ 'for a compound corresponds in each case to one line of Table C.

Table 110

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 111

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 112

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 113

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 114

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 115

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 116

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 117

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 118

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 119

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 120

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, H ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 121

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 122

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 123

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 124

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 125

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 126

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 127

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 128

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 129

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 130

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 131

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 132

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a Ver each corresponds to one row of Table C.

Table 133

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 134

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 135

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 136

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 137

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 138

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, H ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a Ver compound corresponds to one row of Table C.

Table 139

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 140

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 141

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 142

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 143

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 144

Compounds of the formula IA.9, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a Ver each corresponds to one row of Table C.

Table 145

Compounds of the formula IC.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A speaks accordingly.

Table 146

Compounds of the formula IC.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A speaks accordingly.

Table 147

Compounds of formula IC.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A corresponds.

Table 148

Compounds of the formula IC.1, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 149

Compounds of the formula IC.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound each have one row of Table A corresponds.

Table 150

Compounds of the formula IC.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound each have one row of Table A corresponds.

Table 151

Compounds of the formula IC.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 152

Compounds of the formula IC.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 153

Compounds of the formula IC.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A corresponds.

Table 154

Compounds of the formula IC.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A speaks accordingly.

Table 155

Compounds of the formula IC.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of table A corresponds.

Table 156

Compounds of the formula IC.2, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case one row of Table A corresponds.

Table 157

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A speaks accordingly.

Table 158

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A speaks accordingly.

Table 159

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound each have one row of Table A corresponds.

Table 160

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound each have one row of Table A speaks accordingly.

Table 161

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound each have one row of Table A corresponds.

Table 162

Compounds of the formula IC.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound each have one row of Table A corresponds.

Table 163

Compounds of formula IC.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 164

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 165

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 166

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 167

Compounds of formula IC.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 168

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 169

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 170

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 171

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 172

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 173

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 174

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 175

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 176

Compounds of formula IC.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 177

Compounds of formula IC.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 178

Compounds of formula IC.4, in which X, Y and Z for = CH-, H ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 179

Compounds of formula IC.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 180

Compounds of formula IC.4, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 181

Compounds of the formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 182

Compounds of formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 183

Compounds of the formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 184

Compounds of formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 185

Compounds of formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 186

Compounds of formula IC.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ corresponds to one row of Table B for a connection.

Table 187

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 188

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 189

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 190

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 191

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 192

Compounds of formula IC.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 193

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 194

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 195

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 196

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 197

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 198

Compounds of formula IC.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 199

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 200

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 201

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 202

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 203

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 204

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 205

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 206

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 207

Compounds of the formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 208

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 209

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 210

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds to one row of Table C.

Table 211

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 212

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 213

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 214

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 215

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 216

Compounds of formula IC.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a Ver compound corresponds to one row of Table C.

Table 217

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 218

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 219

Compounds of formula IC.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ³ for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 220

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 221

Compounds of formula IC.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 222

Compounds of formula IC.6, in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a Ver each corresponds to one row of Table C.

Table 223

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 224

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 225

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 226

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 227

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 228

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for 99999 00070 552 001000280000000200012000285919988800040 0002019834557 00004 99880r chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a connection corresponds in each case to one row of table A.

Table 229

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 230

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 231

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 232

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 233

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 234

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 235

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 236

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 237

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 238

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound corresponds in each case to one row of table A.

Table 239

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 240

Compounds of formula IC.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and D 'for a compound in each case corresponds to one row of table A.

Table 241

Compounds of the formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 242

Compounds of formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 243

Compounds of formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 244

Compounds of formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 245

Compounds of formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ for one connection each corresponds to one row of Table B.

Table 246

Compounds of formula IC.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl and the combination of the radicals R ² , R ³ and R ⁴ corresponds to one row of Table B for a connection.

Table 247

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 248

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 249

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 250

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 251

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 252

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 253

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 254

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 255

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 256

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 257

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 258

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 259

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 260

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 261

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 262

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ⁴ 'for a compound corresponds in each case to one line of Table C.

Table 263

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 264

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 265

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 266

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 267

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 268

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 269

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 270

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds to one row of Table C.

Table 271

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 272

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 273

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 274

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 275

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 276

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a Ver compound corresponds to one row of Table C.

Table 277

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 278

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 279

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 280

Compounds of formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 281

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 282

Compounds of the formula IC.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds to one row of Table C.

Table 283

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 284

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 285

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 286

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 287

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 288

Compounds of formula ID.1 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 289

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 290

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 291

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 292

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 293

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 294

Compounds of formula ID.2 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 295

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 296

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 297

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 298

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 299

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for 3 hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound corresponds in each case to one row of table A.

Table 300

Compounds of formula ID.3 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a compound in each case corresponds to one row of table A.

Table 301

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 302

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 303

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 304

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 305

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 306

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for methyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 307

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 308

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 309

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 310

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 311

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 312

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for trifluoromethyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 313

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 314

Compounds of the formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 315

Compounds of the formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 316

Compounds of formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 317

Compounds of the formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a connection corresponds in each case to one row of Table A.

Table 318

Compounds of the formula ID.4 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a connection corresponds in each case to one row of Table A.

Table 319

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 320

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 321

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ³ for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 322

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 323

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 324

Compounds of the formula ID.5 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a connection each correspond to one row of Table B.

Table 325

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 326

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 327

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 328

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 329

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 330

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 331

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 332

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 333

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 334

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 335

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 336

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 337

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 338

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 339

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 340

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 341

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 342

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 343

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 344

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 345

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 346

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 347

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 348

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 349

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 350

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 351

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 352

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 353

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 354

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 355

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 356

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 357

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 358

Compounds of the formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 359

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 360

Compounds of formula ID.6 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 361

Compounds of formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 362

Compounds of formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection.

Table 363

Compounds of formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and D 'corresponds to one row of Table A for a connection

Table 364

Compounds of formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for one connection each corresponds to one row of table A.

Table 365

Compounds of formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a connection corresponds in each case to one row of Table A.

Table 366

Compounds of the formula ID.7 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ² for cyclopropyl, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and D 'for a connection corresponds in each case to one row of Table A.

Table 367

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 368

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 369

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 370

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 371

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a compound corresponds in each case to one row of Table B.

Table 372

Compounds of the formula ID.8 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl and the combination of the radicals R ² , R ³ and R ⁴ for a connection each correspond to one row of Table B.

Table 373

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 374

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 375

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 376

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 377

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 378

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 379

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 380

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 381

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 382

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 383

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 384

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for hydrogen, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 385

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 386

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 387

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 388

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 389

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 390

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 391

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 392

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 393

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 394

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 395

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 396

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for methyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 397

Compounds of the formula ID.9 in which x, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 398

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 399

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 400

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 401

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 402

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for methyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 403

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 404

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 405

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for methyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 406

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for methoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 407

Compounds of formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for ethoxy, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table 408

Compounds of the formula ID.9 in which X, Y and Z for = CH-, R ¹ for hydrogen, R ^A for chlorine, R ^B for oxygen, R ^C for ethyl, R ^a for methyl, R ² for methyl, R ³ for ethyl, R ⁴ for ethyl and the radical R ^{4 '} for a compound corresponds in each case to one line of Table C.

Table C.

The compounds I are suitable as fungicides. You stand out due to its excellent effectiveness against a wide range of phytopathogenic fungi, in particular from the class of Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes, out. Some of them are systemic and can be used in plants protection can be used as foliar and soil fungicides.

They are particularly important for combating a large number of mushrooms on various crops such as wheat, rye, Barley, oats, rice, corn, grass, bananas, cotton, soy, coffee fairy, sugar cane, wine, fruit and ornamental plants and vegetables like cucumbers, beans, tomatoes, potatoes and squash, like that like the seeds of these plants.

They are particularly suitable for combating the following plant diseases:

• - Alternaria species in vegetables and fruits,
• - Botrytis cinerea (gray mold) on strawberries, vegetables, ornaments plants and vines,
• - Cercospora arachidicola on peanuts,
• - Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin grow,
• - Erysiphe graminis (powdery mildew) on cereals,
• - Fusarium and Verticillium species on different plants,
• - Helminthosporium species on cereals,
• - Mycosphaerella species on bananas and peanuts,
• - Phytophthora infestans on potatoes and tomatoes,
• - Plasmopara viticola on vines,
• - Podosphaera leucotricha on apples,
• Pseudocercosporella herpotrichoides on wheat and barley,
• - Pseudoperonospora species on hops and cucumbers,
• - Puccinia species on cereals,
• - Pyricularia oryzae on rice,
• - Rhizoctonia species on cotton, rice and lawn,
• - Septoria nodorum on wheat,
• - Uncinula necator on vines,
• - Ustilago species on cereals and sugar cane, as well
• - Venturia species (scab) on apples and pears.

The compounds I are also suitable for combating harmful substances mushrooms like Paecilomyces variotii in material protection (e.g. wood, Paper, dispersions for painting, fibers or fabrics) and in Storage protection.  

The compounds I are applied by using the mushrooms or the plants, seeds, materials to be protected from fungal attack s or the soil with a fungicidally effective amount of active fabrics treated. The application can be done both before and after Infection of materials, plants or seeds by the fungi respectively.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% active ingredient.

The application rates are depending on the application in crop protection Depending on the desired effect, between 0.01 and 2.0 kg of active ingredient fabric per ha.

When treating seeds, amounts of active ingredient are generally used from 0.001 to 0.1 g, preferably 0.01 to 0.05 g per kilogram Seed needed.

When used in the protection of materials or stocks, the application rate of active ingredient according to the type of application and the desired effect. Usual application rates are in Material protection, for example 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of treated material.

The compounds of formula I are also suitable for effectively combating animal pests from the class of insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests:

• - Insects from the order of the butterflies (Lepidoptera) for example Agrotis ypsilon, Agrotis segetum, Alabama argilla cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumif erana, Choristoneura occidentalis, cirphis unipuncta, cydia pomonella, dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insu lana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Heiferia lycopersi cella, Lambdina fiscellaria, Laphygma exigua, Leucoptera cof feella, Leucoptera scitella, Lithocolletis blancardella, lobe sia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis  flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseu doplusia includens, Rhyacionia frustrana, Scrobipalpula abso luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thauinato poea pityocampa, Tortrix viridana, Trichoplusia ni and Zeira phera canadensis,
• - Beetles (Coleoptera), e.g. B. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Bla piniperda stophagus, Blitophaga undata, Bruchus rufimanus, Bru chus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebu losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr hynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir tipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera fountain tennis, hypera postica, ips typographus, lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californi cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,
• - Two-winged (Diptera), e.g. B. Aedes aegypti, Aedes vexans, Anas trepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, fan nia canicularis, Gasterophilus intestinalis, glossina morsi tans, Kaematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifo lii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lyco ria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagole tis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole racea and tipula paludosa,
• - Thrips (Thysanoptera), e.g. B. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
• - Hymenoptera, e.g. B. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testu dinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,  
• Bugs (Heteroptera), e.g. B. Acrosternum hilare, Blissus leucop terus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus in termedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Ne zara viridula, Piesma guadrata, Solubea insularis and Thyanta perditor,
• - Plant suckers (Homoptera), e.g. B. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce rosipha gossypii, Dreyfusia nordinannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa lomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sap paphis mali, Schizaphis graminum, Schizoneura lanuginosa, Tria leurodes vaporariorum and viteus vitifolii,
• - Termites (Isoptera), e.g. B. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
• - Straight wing aircraft (Orthoptera), e.g. B. Acheta domestica, Blatta orien talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano plus femur rubrum, Melanoplus mexicanus, Melanoplus sanguini pes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
• - Arachnoid such as arachnids (Acarina), e.g. B. Amblyomma america num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni cis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius me Gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetra nychus pacificus, Tetranychus telarius and Tetranychus urticae,
• - Nematodes such as root gall nematodes, e.g. B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming Nematodes, e.g. B. Globodera rostochiensis, Heterodera avenae, He terodera glycines, heterodera schachtii, heterodera trifolii, Stick and leaf flakes, e.g. B. Belonolaimus longicaudatus, Dity lenchus destructor, Ditylenchus dipsaci, Heliocotylenchus mul ticinctus, Longidorus elongatus, Radopholus similis, Rotylen chus robustus, Trichodorus primitivus, Tylenchorhynchus clay toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty  lenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The amount of active ingredient used to combat animal Pests are 0.1 to 2.0 in free field conditions preferably 0.2 to 1.0 kg / ha.

The compounds I can in the usual formulations leads, z. B. solutions, emulsions, suspensions, dusts, Powders, pastes and granules. The application form depends according to the respective purpose; in any case, it should be fine and uniform distribution of the Ver ensure loyalty.

The formulations are prepared in a known manner, e.g. B. by stretching the active ingredient with solvents and / or Carriers, if desired using emulsifier agents and dispersants, where in the case of water as Ver other organic solvents as auxiliary solvents can be used. As auxiliary agents come there for essentially: solvents such as aromatics (e.g. Xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. Petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. Cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and what ser; Carriers such as natural rock powder (e.g. kaolins, Clays, talc, chalk) and synthetic stone powder (e.g. finely divided silica, silicates); Emulsifiers like not ionogenic and anionic emulsifiers (e.g. polyoxyethylene fatty al alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants agents such as lignin sulfite liquor and methyl cellulose.

Alkali, alkaline earth, ammonium come as surface-active substances salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsul fonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, Al kyl sulfates, alkyl sulfonates, fatty alcohol sulfates and fatty acids such as their alkali and alkaline earth salts, salts of sulfated Fatty alcohol glycol ether, condensation products of sulfonated Naphthalene and naphthalene derivatives with formaldehyde, condensate onproducts of naphthalene or naphthalene sulfonic acid Phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxy lated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl poly ether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates sate, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxy lated polyoxypropylene, lauryl alcohol polyglycol ether acetal, Sor bitester, lignin sulfite and methyl cellulose.  

For the production of directly sprayable solutions, emulsions, Pastes or oil dispersions come from medium oil fractions rem to high boiling point, such as kerosene or diesel oil, further Coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated Naphthalenes or their derivatives, methanol, ethanol, propanol, Butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclo hexanone, chlorobenzene, isophorone, strongly polar solvents, e.g. B. Dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, into consideration.

Powders, materials for spreading and dusts can be mixed or mixed joint grinding of the active substances with a solid Carrier are manufactured.

Granules, e.g. B. coating, impregnation and homogeneous granules te, can by binding the active ingredients to solid carriers getting produced. Solid carriers are e.g. B. mineral soils, such as silica gel, silicas, silica gels, silicates, talc, Kao lin, attackclay, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ge ground plastics, fertilizers, such as. B. ammonium sulfate, amino nium phosphate, ammonium nitrate, urea and herbal product such as cereal flour, tree bark, wood and nutshell flour, Cel Loose powder and other solid carriers.

The formulations generally contain between 0.01 and 95 % By weight, preferably between 0.1 and 90% by weight of the active ingredient. The active ingredients are in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Examples of formulations are:

• I. 5 parts by weight of a compound according to the invention 95 parts by weight of finely divided kaolin intimately mixed. Man he in this way holds a dusts that 5 wt .-% of Contains active ingredient.
• II. 30 parts by weight of a compound according to the invention are with a mixture of 92 parts by weight of powdered pebble acid gel and 8 parts by weight paraffin oil, which is on the surface this silica gel was sprayed, mixed intimately. Man receives a treatment of the active ingredient in this way good adhesion (active ingredient content 23% by weight).  
• III. 10 parts by weight of a compound according to the invention are in dissolved a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide to 1 mol of oleic acid-N-monoethanolamide, 2 parts by weight of calcium salt the dodecylbenzenesulfonic acid and 2 parts by weight of the plant approximately 40 moles of ethylene oxide to 1 mole of castor oil stands (active ingredient content 9 wt .-%).
• IV. 20 parts by weight of a compound according to the invention are in dissolved a mixture consisting of 60 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 5 parts by weight of the addition pro product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and Parts by weight of the adduct of 40 moles of ethylene oxide 1 mol of castor oil (active ingredient content 16% by weight).
• V. 80 parts by weight of a compound of the invention 3 parts by weight of the sodium salt of diisobutylnaphthalene-al pha-sulfonic acid, 10 parts by weight of the sodium salt Lignin sulfonic acid from a sulfite waste liquor and 7 parts by weight powdered silica gel well mixed and in one Chamber mill, ground (active ingredient content 80% by weight).
• VI. 90 parts by weight of a Ver according to the invention are mixed bond with 10 parts by weight of N-methyl-α-pyrrolidone and receives a solution that is used in the form of tiny drops is suitable (active ingredient content 90% by weight).
• VII. 20 parts by weight of a compound according to the invention are described in dissolved a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the addition pro product of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 Parts by weight of the adduct of 40 moles of ethylene oxide of 1 mole of castor oil. By pouring and fine Ver dividing the solution in 100,000 parts by weight of water is obtained an aqueous dispersion containing 0.02% by weight of the active ingredient holds.
• VIII. 20 parts by weight of a compound according to the invention are with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α- sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight pul deformed silica gel well mixed and in a ham grind grinder. By finely distributing the mixture in 20,000 parts by weight of water are obtained from a spray mixture which Contains 0.1% by weight of the active ingredient.

The active ingredients as such, in the form of their formulations or the application forms prepared from it, e.g. B. in the form of di sprayable solutions, powders, suspensions or dispersers sions, emulsions, oil dispersions, pastes, dusts, litter averaging, granules by spraying, atomizing, dusting, ver sprinkle or pour. The application forms rich depending on the purposes; they should be in everyone If possible, the finest distribution of the active ingredient according to the invention ensure fabrics.

Aqueous application forms can be made from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) through Zu set of water to be prepared. For the production of emulsions, Pastes or oil dispersions can contain the substances as such or dissolved in an oil or solvent, using wetting, adhesive, Dispersants or emulsifiers are homogenized in water.

However, wetting, adhesive, Dispersing or emulsifying agent and possibly solvent or Oil existing concentrates are made for dilution are suitable with water.

The drug concentrations in the ready-to-use Zu Preparations can be varied in larger areas. In all they are generally between 0.0001 and 10%, preferably between between 0.01 and 1%.

The active ingredients can also be used successfully in ultra-low-volume Procedure (ULV) can be used, where it is possible to form stungen with more than 95 wt .-% active ingredient or even the active ingredient without applying additives.

Oils of various types, herbicides, fun gicides, other pesticides, bactericides, given if necessary, only immediately before use (tank mix) be set. These agents can be used with the invention be mixed in a weight ratio of 1:10 to 10: 1.

The agents according to the invention can be used as Fungicides are also present together with other active ingredients e.g. B. with herbicides, insecticides, growth regulators, fungicides that or with fertilizers. When mixing the connections I or the agents containing it in the application form as fun In many cases, one obtains gicides with other fungicides Enlargement of the fungicidal spectrum of activity.  

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:

• - Sulfur, dithiocarbamates and their derivatives, such as Ferridi methyldithiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisdithiocarbamate, manganese ethylene bisdithiocarbamate, manganese zinc ethylenediamine bis-dithiocarbamate, tetramethylthiuram disulfide, Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate), Am monia complex of zinc (N, N'-propylene-bis-dithiocarbamate), Zinc (N, N'-propylene bis-dithiocarbamate), N, N'-polypropylene bis- (thiocarbamoyl) disulfide;
• Nitroderivatives, such as dinitro- (1-methylheptyl) phenylcrotonate, 2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate, 2-sec-Bu tyl-4,6-dinitrophenyl-isopropyl carbonate, 5-nitro-isophthalic acid re-di-isopropyl ester;
• - Heterocyclic substances, such as 2-heptadecyl-2-imidazolin-ace tat, 2,4-dichloro-6- (o-chloroanilino) -s-triazine, O, O-diethyl phthalimidophosphonothioate, 5-amino-1- [bis- (dimethylami no) -phosphinyl] -3-phenyl-1,2,4-triazole, 2,3-dicyano-1,4-di thioanthraquinone, 2-thio-1,3-dithiolo [4,5-b] quinoxaline, 1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole, 2- (furyl- (2)) -benz imidazole, 2- (thiazolyl- (4)) benzimidazole, N- (1,1,2,2-tetra chloroethylthio) tetrahydrophthalimide, N-trichloromethylthio-te trahydrophthalimide, M-trichloromethylthio-phthalimide,
• - N-dichlorofluoromethylthio-N ', N'-dimethyl-N-phenylsulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole, 2-rhodanme thylthiobenzthiazole, 1,4-dichloro-2,5-dimethoxybenzene, 4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone, Pyridine-2-thio-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-oxathiin-4,4-dioxide, 2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide, 2-methyl furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid anilide, 2,4,5-trimethyl-furan-3-carboxylic acid anilide, 2,5-dime thyl-furan-3-carboxylic acid cyclohexylamide, M-cyclohexyl-N-me thoxy-2,5-dimethyl-furan-3-carboxamide, 2-methyl-benzoic acid re-anilide, 2-iodo-benzoic acid anilide, N-formyl-N-morpho lin-2,2,2-trichloroethyl acetal, piperazin-1,4-diylbis-1- (2,2,2-trichloroethyl) formamide, 1- (3,4-dichloroanilino) -1-formy lamino-2,2,2-trichloroethane, 2,6-dimethyl-N-tridecyl-morpholine or its salts, 2,6-dimethyl-N-cyclododecyl-morpholine or its salts, N- [3- (p-tert-butylphenyl) -2-methylpro pyl] cis-2,6-dimethylmorpholine, N- [3- (p-tert-butylphe nyl) -2-methylpropyl] piperidine, 1- [2- (2,4-dichlorophenyl) - 4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole, 1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl  ethyl] -1H-1,2,4-triazole, N- (n-propyl) -N- (2,4,6-trichlorophen oxyethyl) -N'-imidazol-yl urea, 1- (4-chlorophenoxy) -3,3-di methyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, 1- (4-chlorophen oxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, (2RS, 3RS) -1- [3- (2-chlorophenyl) -2- (4-fluorophenyl) oxiran-2-ylme thyl] -1H-1,2,4-triazole, α- (2-chlorophenyl) -α- (4-chlorophe nyl) -5-pyrimidine-methanol, 5-butyl-2-dimethylamino-4-hydro xy-6-methyl-pyrimidine, bis- (p-chlorophenyl) -3-pyridine-methanol, 1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene, 1,2-bis (3-methoxycarbonyl-2-thioureido) benzene,
• - Strobilurins such as methyl-E-methoxyiinino- [α- (o-tolyloxy) -o-to lyl] acetate, methyl E-2- [2- [6- (2-cyanophenoxy) pyrimidin-4-yl oxy] phenyl) -3-methoxyacrylate, methyl-E-methoxyimino- [α- (2- phenoxyphenyl)] - acetamide, methyl-E-methoxyimino- [α- (2,5-dime thylphenoxy) -o-tolyl] -acetamide,
• Anilinopyrimidines such as N- (4,6-dimethylpyrimidin-2-yl) aniline, N- [4-methyl-6- (1-propynyl) pyrimidin-2-yl] aniline, N- [4-Me thyl-6-cyclopropyl-pyrimidin-2-yl] aniline,
• Phenylpyrroles such as 4- (2,2-difluoro-1,3-benzodioxol-4-yl) pyr rol-3-carbonitrile,
• - Cinnamic acid amides such as 3- (4-chlorophenyl) -3- (3,4-dimethoxyphe nyl) acrylic acid morpholide,
• - and various fungicides, such as dodecylguanidine acetate, 3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide, Hexachlorobenzene, DL-methyl-N- (2,6-dimethyl-phenyl) -N-fu royl (2) alaninate, DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyace tyl) -alanine-methyl-ester, N- (2,6-dimethylphenyl) -N-chloroacetyl- D, L-2-aminobutyrolactone, DL-N- (2,6-dimethylphenyl) -N- (phenyla cetyl) alaninine ethyl ester, 5-methyl-5-vinyl-3- (3, 5-dichlor phenyl) -2,4-dioxo-1,3-oxazolidine, 3- (3,5-dichlorophenyl) -5-me thyl-5-methoxymethyl-1,3-oxazolidine-2,4-dione, 3- (3,5-dichloro phenyl) -1-isopropylcarbamoylhydantoin, N- (3,5-dichlor phenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, 2-cya no- [N- (ethylaminocarbonyl) -2-methoximino] acetamide, 1- [2- (2,4- Dichlorophenyl) pentyl] -1H-1,2,4-triazole, 2,4-difluoro-α- (1H- 1,2,4-triazolyl-1-methyl) -benzhydryl alcohol, N- (3-chloro-2,6- dinitro-4-t 14208 00070 552 001000280000000200012000285911409700040 0002019834557 00004 14089rifluoromethyl-phenyl) -5-trifluoromethyl-3-chloro-2- aminopyridine, 1 - ((bis- (4-fluorophenyl) methylsilyl) me thyl) -1H-1,2,4-triazole.

Synthesis examples

The examples given in the synthesis examples below Writings were made with a corresponding modification of the output compounds used to obtain further compounds I. The  Compounds thus obtained are in the tables below listed with physical details.

step 1

Synthesis of 3-bromobenzyl isocyanate

75 g (0.34 mol) of 3-bromobenzylamine hydrochloride were suspended in 300 ml of 1,1,1-trichloroethane and 33.3 g (0.11 mol) of triphosgene in 200 ml of 1,1,1-trichloroethane were added dropwise at room temperature. At the reflux temperature, 1.5 eq. Triphosgene added dropwise within 4 hours. After a total of 16 hours of reflux, fractional distillation was carried out. 55.8 g of the title compound were obtained as a colorless liquid with a boiling point of _0.6 90-91 ° C.

Level 2

Synthesis of N- (3-bromobenzyl) -2,2-dimethylhydrazinecarboxamide

12.1 g (200 mmol) of 1,1-dimethylhydrazine were in 200 ml of dichlor submitted methane and 42.8 g (200 mmol) of isocyanate from stage 1, in 50 ml dichloromethane dissolved, added dropwise at 20 to 25 ° C. To 3 hrs stirring at room temperature became the volatile parts distilled off. 55 g of the title ver obtained bond of mp 84-85 ° C.

level 3

Synthesis of 5-chloro-4- (3-bromobenzyl) -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A suspension of 70 g (260 mmol) of the compound from stage 2 in 450 ml of 1,1,1-trichloroethane was at 60 ° C with 76.3 g (260 mmol) Triphosgene added in 200 ml of 1,1,1-trichloroethane. Within For 4 hours at the reflux temperature 50 g triphosgene in 130 ml 1,1,1-trichloroethane added. Then the solvent was removed  breastfeeding. After chromatography on Kie selgel (toluene-ethyl acetate mixture 9: 1) 47.7 g of the Ti Tel connection obtained from mp. 87-89 ° C.

Level 4

Synthesis of 5-chloro-4- [3- (2-methoxyphenyl) benzyl] -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A mixture of 3.0 g (10 mmol) of the triazolone from step 3, 3.0 g (20 mmol) of 2-methoxy-phenylboronic acid and 1 spatula tip of tetrais (triphenylphosphine) -Pd (O) in 20 ml of ethylene glycol dimethyl ether was used Mix with a solution of 3.2 g (30 mmol) sodium carbonate in 10 ml water refluxed for 4 hours. Then the reaction mixture was poured onto 50 ml of cyclohexane and ice. After phase separation, the aqueous phase was extracted with cyclohexane. The combined organic phases were washed with 50 ml of 2N sodium hydroxide solution, then with saturated NaCl solution, dried and freed from the solvent. Chromatography on silica gel (toluene / ethyl acetate mixture 4: 1) gave the residue:
1.7 g of the title compound
IR: 1721, 1537, 1500, 1464, 1405, 1239, 756, 739 cm ^-1 and
1.2 g of 5- (2-methoxyphenyl) -4- [3- (2-methoxyphenyl) benzyl] -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one
IR: 1707, 1609, 1469, 1257, 1240, 1025, 754 cm ^-1 obtained.

Level 5

Synthesis of 5-methoxy-4- [3- (2-methoxyphenyl) benzyl] -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A solution of 0.8 g (2.4 mmol) of the title compound from stage 4 in 5 ml of methanol and 5 ml of 1,2-dimethoxyethane was added after adding 3.6 mmol of sodium methoxide (as a 30% solution in methanol) for 3 , Refluxed for 5 hours, then the volatile constituents were removed in vacuo. The residue was digested in ethyl acetate. After chromatography on silica gel (toluene / ethyl acetate mixture 9: 1), 0.3 g of the title compound was obtained from the filtrate.
IR: 1724, 1610, 1508, 1478, 1464, 1419, 1240, 1026, 749 cm ^-1 .

Example 2

step 1

Synthesis of 3-methylbenzyl isocyanate

A suspension of 86 g (0.55 mol) of 3-methylbenzylamine hydrochloride in 300 ml of 1,1,1-trichloroethane was at 20 to 25 ° C with 59.7 g (0.2 mol) of triphosgene in 250 ml of 1.1 , 1-Trichloroethane added dropwise. 1 eq. Add triphosgene in 1,1,1-tri chloroethane, then fractional distillation. 74 g of 3-methylbenzyl isocyanate were obtained as a colorless liquid with a boiling point of _0.4-0.6 50-52 ° C.

Level 2

Synthesis of N- (3-methylbenzyl) -2,2-dimethylhydrazine car boxamide

A solution of 30 g (0.5 mol) 1,1-dimethylhydrazine in dichlorme than was presented at 20 to 25 ° C with a solution of 74 g (0.5 mol) 3-methylbenzyl isocyanate from stage 1 in dichloromethane transferred. After stirring for 1 hour, the solvent was distilled off liert. 104 g of the title compound of Mp. 66-68 ° C obtained.

level 3

Synthesis of 5-chloro-4- (3-methylbenzyl) -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A solution of 104 g (0.5 mol) of the carboxamide from stage 2 in 1,1,1-trichloroethane was treated with 148.5 g (0.5 mol) of triphosgene 1,1,1-trichloroethane at 20 to 25 ° C. Then was it refluxed for about 6 hours, during which time 0.5 eq. Triphos gene dissolved in 1,1,1-trichloroethane, added. After distillery Ren of the solvent and chromatography of the residue Silica gel (toluene-ethyl acetate mixture 9: 1) became 71.6 g obtained the title compound with the mp. 68-69 ° C.

Level 4

5-chloro-4- [3- (bromomethyl) benzyl] -2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A solution of 35.6 g (150 mmol) of the title compound from step 3 in 350 ml of carbon tetrachloride was added after adding 29.4 g (165 mmol) N-bromosuccinimide and a spatula tip azobisisobuty ronitrile (AIBM) heated to reflux with a daylight lamp. After 30 min, the mixture was poured onto ice / saline solution, then with Extracted dichloromethane. The combined organic phases were washed neutral, dried and concentrated in vacuo. To The residue was digested with diisopropyl ether, 26.8 g of Obtained title compound of mp 81-83 ° C.

Level 5

5-chloro-4- (3 - [(2-methyl) phenoxy] methyl) benzyl-2,4-dihydro-2-methyl-3H-1,2,4-triazol-3-one

A solution of 0.68 g (6.3 mmol) of 2-methylphenol (o-cresol) in 20 ml of anhydrous tetrahydrofuran (THF) was tert-potassium at 20 to 25 ° C with 0.74 g (6.6 mmol) -Butylate added. After stirring at 40 ° C. for about 30 minutes, the solvent was distilled off. The residue was dissolved in 20 ml of anhydrous dimethylformamide (DMF) and added dropwise to a solution of 2 g (6.3 mmol) of the title compounds from stage 4 in 20 ml of anhydrous DMF. After stirring for 30 min, the mixture was poured onto an ice / sodium chloride solution and extracted with methyl tert-butyl ether. The combined organic phases were washed with 2N sodium hydroxide solution, then with water. After drying, the solvent was distilled off. 2.1 g of the title compound were obtained from the residue.
IR: 1722, 1537, 1496, 1440, 1407, 1384, 1239, 1193, 1122, 751 cm ^-1 .

Level 6

5-methoxy-4- {3 - [(2-methyl) phenoxy] methyl} benzyl-2,4-di hydro-2-methyl-3H-1,2,4-triazol-3-one

The solution of 1.5 g (4.4 mmol) of the title compound from stage 5 in 40 ml of a methanol / 1,2-dimethoxyethane mixture (1: 1) was mixed with 5.2 mmol of sodium methoxide at 20 to 25 ° C. (as a 30% solution in methanol) refluxed for 4 hours, then the volatiles were removed in vacuo. The residue was digested in ethyl acetate. After chromatography on silica gel (9: 1 mixture of toluene and ethyl acetate), 0.6 g of the title compound was obtained from the filtrate.
IR: 1725, 1610, 1508, 1497, 1419, 1239, 1122, 1051, 752 cm ^-1 .

Examples of the action against harmful fungi 1. Effect of the compounds as mitochondrial inhibitors breathing

To the effect of the compounds of the invention on the mito To determine chondrial respiration, the mitochondria must first be determined be isolated from the organisms to be examined. To do this in the case of the yeast Saccharomyces cerevisiae a 30 to 40% cell suspension of the fungus in an aqueous solution of 0.6 M mannitol + 0.01 M tris [hydroxymethyl] aminomethane + 0.002 M Ethylene diamine tetraacetic acid disodium salt (pH 6.8) with a Glass ball mill unlocked and the extract by differen fractional centrifugation at 1000 × g and 12000 × g. The mitochondria are in the 12000 × precipitation g centrifugation.

Similarly, mitochondria can be isolated from other fungi the, e.g. B. from the phytopathogenic fungus Drechslera sorokiniana (synonym Helminthosphorium sativum), from the human pathogenic Dermatophyte Trichophyton mentagrophytes as well as from other organs nisms, e.g. B. from the housefly (musca domestica) as an insect or from the spider mite Tetranychus urticae.

The effect of the compounds on the respiratory chain is determined by adding to a suspension of mitochondria in an aqueous solution of 0.01 M tris [hydroxymethyl] aminomethane + 0.65 M sorbitol + 0.01 M KH ₂ PO ₄ + 0.01 M KCl + 0.0004 M ethylenediaminetetraacetic acid disodium salt + 0.3% bovine serum albumin + 0.0007 M KCN + 6 x, 10 ^-6 ubiquinone-50 + 0.01 M Na succinate + 0.15% cytochrome c (pH 7.5) a solution of the compound to be investigated is given in dimethyl sulfoxide and the rate of reduction of the cytochrome c is determined photometrically on the basis of the increase in extinction at 546 nm. A batch with the corresponding amount of pure DMSO serves as a control. The inhibitory value for the active substance concentration specified in each case is then calculated as follows.

where ΔE is the change in extinction, Δt is the change in time,

the rate of sales of the control and

means the turnover rate of the sample x.

The following table shows for a number of the invention Compounds whose effect as a respiratory inhibitor on the mitochon three of the yeast Saccharomyces cerevisiae, the phyto pathogenic fungus Drechslera sorokiniana and the house fly musca domestica.

The inhibition of mitochondrial respiration is given in each case as an I ₅₀ value (this is the concentration of test substance at which 50% inhibition occurs) and as an F value, which is a relative value which is defined as follows:

The so-called enol ether stilbene of the following formula serves as the standard substance:

Table II

Inhibition of mitochondrial respiration by compounds of the formula I from Table I

The fungicidal activity of the compounds of the general formula I was demonstrated by the following tests:
The active ingredients were separated or together as a 10% emulsion in a mixture of 70% by weight cyclohexanone, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10% by weight .-% Wettol® EM (non-ionic emulsifier based on ethoxylated ricinus oil) prepared and diluted with water according to the desired concentration.

Examples of the action against animal pests

The activity of the compounds of the general formula I against animal pests was demonstrated by the following experiments:
The active ingredients were

• a. as a 0.1% solution in acetone or
• b. as a 10% emulsion in a mixture of 70% by weight cyclohex anon, 20% by weight Nekanil® LN (Lutensol® AP6, wetting agent with Emulsifying and dispersing action based on ethoxylated Alkylphenols) and 10% by weight Wettol® EM (non-ionic emuls gator based on ethoxylated castor oil) processed and in accordance with the desired concentration Acetone in the case of a. or with water in the case of b. diluted.

After the end of the tests, the lowest Kon center determined at which the connections compared to untreated controls an 80 to 100% inhibition or Cause mortality (threshold of action or minimum concentration).

Claims (13)

1. (hetero) aryl compounds of the formula I,
in which the substituents have the following meaning
X, Y, Z independently of one another = N- or = CR ¹ -, where
R ¹ may be the same or different and are hydrogen, cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkyl thio or C ₁ -C ₄ haloalkylthio;
V -CH ₂ -, NR ^a -, -O-, -S-, -C (= O) - or -C (= CR ^a ₂ ) -, where
R ^{a is} hydrogen or C ₁ -C ₄ alkyl;
W is a group A or B,
in the
# indicates the bond with group V and
R ^A for halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl thio, a group E or NR ^a R ^b , wherein
E if necessary subst. Alkyl, optionally subst. Alkenyl, if necessary subst. Alkynyl, optionally subst. Cycloalkyl, optionally subst. Cycloalkenyl, optionally subst. Heterocyclyl, optionally subst. Aryl or optionally subst. Hetaryl,
R ^a , R ^{b are} independently hydrogen or C ₁ -C ₄ alkyl;
R ^B for oxygen or sulfur and
R ^{C is} hydrogen or C ₁ -C ₄ alkyl;
U is a direct bond, oxygen or oxymethylene (-OCH ₂ -);
G a) if U is oxygen or oxymethylene, a group D, EC (R ² ) = N, R ⁴ ON = C (R ³ ) -C (R ² ) = N or R ⁴ ON = C (C [R ³ ] = N-OR ⁴ ) -C (R ² ) = N, where
D if necessary subst. Heterocyclyl, optionally subst. Aryl, if necessary subst. Hetaryl, possibly subst. Arylmethylene or optionally subst. Hetarylmethylene;
R ^{2 is} hydrogen, cyano, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₃ -C _6- cycloal kyl;
R ^{3 is} hydrogen, cyano, halogen, or E, EO, ES or EN (R ^d ), where
R ^{d is} hydrogen, C ₁ -C ₄ alkyl, C ₂ -C ₆ alkenyl or C ₂ -C ₆ alkynyl,
R ⁴ hydrogen, optionally subst. C ₁ -C ₄ alkyl, optionally subst. C ₃ -C ₆ cycloalkyl, optionally subst. C ₂ -C ₆ alkenyl or optionally subst. C ₂ -C ₆ alkynyl and
b) if U stands for a direct bond, a group E-, E-CH ₂ -CH ₂ -, E-CH = CH-, EC∼C-, ES-, ES-CH ₂ -, E-CH ₂ - ON = CH (R ^a ) -, EC (= O) -O-CH ₂ -, EC (CH ₃ ) = NN = C (CH ₃ ) -O-CH ₂ or R ^e R ^f N-CH ₂ -, in which
R ^e , R ^f independently of one another for radicals R ⁴ or together for heteroaryl or heteroaryl bonded via nitrogen. 2. (hetero) aryl compounds of the formula I 'according to claim 1,
in which
X, Y, Z = CR ¹ -;
V -CH ₂ - or -NR ^a ;
W is a group A or B, where R ^{B is} oxygen;
G 'is a group D', D'-O-, D'-O-CH ₂ , D'-CH = CH, D'-C∼C, EC (R ² ) = NO-, R ⁴ ON = C ( R ³ ) -C (R ² ) = NO- or R ⁴ ON = C (C [R ³ ] = N-OR ⁴ ) -C (R ² ) = NO- or R ^e R ^f N-CH ₂ , where
D 'if necessary subst. Aryl or optionally subst. Hetaryl,
R ^e , R ^f together for nitrogen-bound heterocyclyl or heteroaryl,
means. 3. Compounds of formula Ia according to claim 1, in which
V -CH ₂ - or -NR ^a - means. 4. Compounds of formula Ib according to claim 1, in which
V -CH ₂ -, -NR ^a -, -O-, -S-, -C (= O) - or -C (= CR ^a ₂ ) - means. 5. Process for the preparation of compounds of formula IA
in which X, Y, Z, R ¹ and R ^{C have} the meaning given in claim 1 and
U oxymethylene or a direct bond;
G a) when U is oxymethylene,
a group D ', where
D 'if necessary subst. Aryl or optionally subst. Hetaryl;
b) if U is a direct bond, a group D ', D'-CH = CH, D'-CC or R ^e R ^f N-CH ₂ , where at
R ^e , R ^f together for nitrogen-bound heterocyclyl or heteroaryl
R ^{A is} chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b ;
R ^B means oxygen
characterized in that (hetero) arylmethylene amines of the formula IIA,
in which Q represents methyl or a nucleophilically cleavable group, with phosgene or a phosgene equivalent to isocyanates of the formula IIIA,
reacted with di-C ₁ -C ₄ alkylhydrazines of the formula IVa
to carbamates of the formula VA
are reacted, VA with phosgene or a phosgene equivalent in triazolones of the formula VIA,
in which R ^A stands for chlorine are transferred, if appropriate with compounds of the formula R ^A -H, in which
R ^{A is} C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b , to triazolones of the formula VIA, in which
R ^{A is} C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b , are reacted, and
in case a),
in which Q is methyl, VIA by halogenation in compounds of the formula VIIA,
in which [Hal] represents a halogen atom, transferred and VIIA by reaction with compounds of the formula VIIIa '
D'-OH VIIIa '
converted into compounds of the formula IA in which U represents oxymethylene and G represents D 'or
in case b),
in which Q represents a nucleophilically cleavable group, VIA by reaction with a compound of the formula VIIIb ',
D'-M VIIIb '
in the
M for a group Mg-Hal, Zn-Hal or B (OR ^a ) ₂ , where
Hal is a halogen atom and
R ^{a is} hydrogen or C ₁ -C ₄ alkyl,
converted into compounds of formula IA, in which U stands for a direct bond and G for D '. 6. Process for the preparation of compounds of formula IB
in which X, Y, Z, R ¹ and R ^{C have} the meaning given in claim 1 and
U oxymethylene or a direct bond;
G a) when U is oxymethylene, a group D ', where
D 'if necessary subst. Aryl or optionally subst. Hetaryl;
b) if U is a direct bond, a group D ', D'-CH = CH, D'-C∼C or R ^e R ^f N-CH ₂ , where at
R ^e , R ^f together for nitrogen-bound heterocyclyl or heteroaryl
R ^{A is} chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b ;
R ^B means oxygen
characterized in that (hetero) arylproplonic acid esters of the formula IIB,
in the Q for methyl or a nucleophilically cleavable group and R 'for C ₁ -C ₆ alkyl or optionally subst. Phenyl is, with formic acid orthoesters or chloroformic acid esters of formula IVb,
in the
R 'for C ₁ -C ₆ alkyl or optionally subst. Phenyl and
R '' for chlorine, C ₁ -C ₆ alkoxy or optionally subst. Phenoxy
stands for malonic esters of the formula IIIB,
in the
R 'for C ₁ -C ₆ alkyl or optionally subst. Phenyl stands
IIIB with N-alkylhydroxylamines of the formula IVc
HO-NHR ^c IVc
to isoxazolones of the formula VB
implemented, VB optionally by reaction with halogenation agents, with alkylating agents or by halogenation and subsequent reaction with amines of the formula HNR ^a R ^b , in isoxazolones of the formula VIB
in which
R ^{A means} halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio or NR ^a R ^b ,
transferred, and
in case a),
in which Q is methyl, VIB by halogenation in compounds of the formula VIIB,
in which [Hal] represents a halogen atom, transferred and VIIB by reaction with compounds of the formula VIIIa
D'-OH VIIIa
converted into compounds of the formula IB in which U is oxymethylene and G is D 'or
in case b),
in which Q represents a nucleophilically cleavable group, VIB by reaction with a compound of the formula VIIIb,
D'-M VIIIb
in the
M for a group Mg-Hal, Zn-Hal or B (OR ^a ) ₂ , where
Hal is a halogen atom and
R ^{a is} hydrogen or C ₁ -C ₄ alkyl,
converted into compounds of the formula IB in which U stands for a direct bond and G for D '. 7. Intermediates of formula 1 according to claim 3
in the
Q is methyl, Hal-CH ₂ , OH or a nucleophilically removable group,
V CH ₂ or NR ^a and
Θ N = C = R ^B , NH-C (= R ^B ) -NH-NR ^C ₂ or a group A, where Q is not OH if Θ N = C = R ^B. 8. Intermediates of formula 2 according to claim 4
in the
Q 'is methyl, Hal-CH ₂ , or a nucleophilically cleavable group. 9. Intermediates of formula 3
in the
R ¹ , X, Y and Z have the meaning given in claim 1,
Q 'is methyl, Hal-CH ₂ , OH or a nucleophilically removable group,
V -CH ₂ -, -C (= O) -, -C (= C [R ^a ] ₂ ) -, oxygen, sulfur, or NR ^a , where
R ^{a is} hydrogen or C ₁ -C ₄ alkyl,
R 'for C ₁ -C ₆ alkyl or optionally subst. Phenyl;
means. 10. To control animal pests or harmful fungi suitable agent containing a solid or liquid Carrier and a compound of general formula I ge according to claim 1. 11. Use of the compounds I according to claim 1 for the manufacture for the control of animal pests or Suitable fungi suitable agent. 12. A method of combating harmful fungi, characterized records that one should protect the mushrooms or those from fungal attack materials, plants, soil or seeds an effective amount of a compound of the general formula I treated according to claim 1. 13. A method for controlling animal pests, thereby characterized in that the animal pests or the materials, plants, the soil to be protected from them or seeds with an effective amount of a compound of the general formula I treated according to claim 1.