DE19623744A1 - Aminophthalic acid derivatives - Google Patents

Abstract

The present application concerns the use of aminophthalic acid derivatives as fungicides, and novel aminophthalic acid derivatives and several processes for their production.

Description

The present application relates to the use of aminophthalic acid derivatives vaten as fungicides, as well as new aminophthalic acid derivatives and several processes for their manufacture.

Certain aminophthalic acid derivatives, such as 3-acetylamino-phthal dimethyl acid ester, 3-aminophthalic acid dimethyl ester, 3-aminophthalic acid diethyl esters, 3-aminophthalic acid 1-methyl ester, 3-aminophthalic acid 2-methyl ester and 3-aminophthalic acid, are already known from the chemical literature (cf. e.g. B. J. Heterocycl. Chem. (1973) 891-9, J. Amer. Chem. Soc., (1937) 2580-3, Justus Liebigs Ann. Chem., (1881) 246, J. Amer. Chem. Soc., (1909) 486, J. Med. Chem. (1988) 1466-1471, Chem. Ber., (1886), 166, JP 04182460).

A fungicidal activity of these compounds has not been described so far been.

It has now been found that the aminophthalic acid derivatives of the general Formula (I),

in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping

where R¹¹ has the meaning given below,
R² is hydrogen or one of the following groups

stands,
wherein
R⁸ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R⁹ represents hydrogen or alkyl, or
R⁸ and R⁹ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl,
R¹⁰ represents alkyl, alkenyl, alkynyl, cycloalkyl which is optionally monosubstituted to trisubstituted by aryl or cycloalkyl or heterocyclyl,
R¹¹ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl or heterocyclyl,
R¹² is alkyl, aryl or heterocyclyl, or
R¹ and R² together for a grouping

stand in what
R¹³ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl and
R¹⁴ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, alkoxy or dialkylamino or
R¹³ and R¹⁴ together with the carbon atom to which they are attached represent cycloalkylidene, or
R¹ and R² together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl,
R³ and R⁴ are the same or different and independently of one another for hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, mercapto, alkylthio, alkenylthio, alkynylthio, arylalkylthio, cycloalkylthio, cycloalkenylthio, aroalkenylthio, aryloalkenylthio, arylalkyl or arylylthio,

stand where
R¹⁵ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R¹⁶ represents hydrogen or alkyl, or
R¹⁵ and R¹⁶ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,
can be used to control pests.

The compounds of formula (I) had a very strong fungicidal activity in crop protection.  

In the definitions are the saturated or unsaturated hydrocarbons material chains, such as alkyl or alkenyl, also in combination with heteroatoms, such as in alkoxy, alkylthio or alkylamino, in each case straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

Aryl stands for aromatic, mono- or polycyclic hydrocarbon rings, such as e.g. B. phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or Naphthyl, especially phenyl.

Heterocyclyl stands for saturated or unsaturated, as well as aromatic, ring-shaped Compounds in which at least one ring member has a heteroatom, i.e. H. one of Carbon is different atom. If the ring contains several heteroatoms, they can be the same or different. If the ring contains several acids atoms of matter, these are not adjacent. Heteroatoms are preferably oxygen, Nitrogen or sulfur.

Cycloalkyl stands for saturated, carbocyclic, ring-shaped compounds.

Cycloalkenyl stands for carbocyclic, ring-shaped compounds that at least contain a double bond.

All of the ring-shaped connections mentioned may form with others carbocyclic or heterocyclic, fused or bridged rings together a polycyclic ring system.

Surprisingly, the substances mentioned in this application show a lot stronger fungicidal activity than constitutionally similar compounds as in for example benzoic acid, with the same direction of action.

Preference is given to using the compounds of the formula (I) in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping

where R11 has the preferred meaning given below,
R² is hydrogen or one of the following groups

stands in what
R⁸ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R⁹ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R⁸ and R⁹ together with the nitrogen atom to which they are bonded represent optionally substituted heterocyclyl with 3 to 7 rings,
R¹⁰ for optionally substituted by phenyl or cycloalkyl with 3 to 8 carbon atoms, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms or for heterocyclyl with 3 to 7 ring members stands,
R¹¹ for hydrogen, each optionally substituted by alkoxycarbonyl, alkylcarbonyl or carboxy-substituted alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or in each case optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen-substituted cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, aryl, arylalkyl or heterocyclyl with 3 to 7 ring members,
R¹² represents alkyl having 1 to 4 carbon atoms, phenyl, naphthyl or heterocyclyl having 3 to 7 ring members, or
R¹ and R² together for a grouping

stand in what
R¹³ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, cycloalkenyl with 3 to 7 carbon atoms, each optionally optionally up to three times substituted by alkyl, alkoxy, halogen, cyano or nitro Phenyl, naphthyl or heterocyclyl with 3 to 7 ring members and
R¹⁴ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, cycloalkenyl with 3 to 7 carbon atoms, phenyl, naphthyl, heterocyclyl with 3 to 7 ring members, alkoxy with 1 to 4 carbon atoms or dialkylamino each having 1 to 4 carbon atoms in the alkyl moieties or
R¹³ and R¹⁴ together with the carbon atom to which they are attached represent cycloalkylidene having 3 to 7 carbon atoms, or
R¹ and R² together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl with 3 to 7 ring members,
R³ and R⁴ are the same or different and independently of one another for hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbons Substance atoms, cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, mercapto, alkylthio with 1 to 4 carbon atoms, alkenylthio with 2 to 4 carbon atoms, alkynylthio with 2 to 4 carbon atoms, arylalkylthio with 1 to 4 carbon atoms in the alkyl part , Cycloalkylthio with 3 to 7 carbon atoms, Cyclo alkenylthio with 3 to 7 carbon atoms, Phenylthio, Heterocyclylthio with 3 to 7 ring members or

stand where
R¹⁵ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl having 3 to 7 ring members,
R¹⁶ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R¹⁵ and R¹⁶ together with the nitrogen atom to which they are attached are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclyl with 3 to 7 members, and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkyl, haloalkoxy or haloalkylthio each because there are 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms.

It is particularly preferred to use the compounds of the formula (I) in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping

stands,
where R¹¹ has the particularly preferred meaning given below,
R² is hydrogen or one of the following groups

stands in what
R⁸ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or in each case optionally up to three times by fluorine, chlorine, bromine, iodine, Methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or difluorochloromethoxy, substituted phenyl, naphthyl, thienyl, pyridyl or furyl,
R⁹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or
R⁸ and R⁹ together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl or piperazinyl which may be monosubstituted to trisubstituted by methyl,
R¹⁰ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, benzyl, 1-phenylethyl, 2-phenylethyl, cyclohexylmethyl, allyl, propargyl, oxethan-3-yl,
R¹¹ for hydrogen, each optionally substituted by methoxycarbonyl, ethoxycarbonyl, acetyl or carboxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1,3 -dien-1-yl or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, thienyl, furyl, pyrazolyl, pyridyl or 2,3-dihydro which are optionally monosubstituted to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine [1,4] oxathiin stands,
R¹² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, phenyl, naphthyl, thienyl, furyl or pyridyl, or
R¹ and R² together for a grouping

stand in what
R¹³ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, methyl phenyl, fluorophenyl, chlorophenyl, bromophenyl, cyanophenyl, methoxyphenyl, nitrophenyl, thienyl, furyl, pyridyl or chloropyridyl and
R¹⁴ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, thienyl, furyl or pyridyl, methoxy, Ethoxy, Dimethylamino, Diethylamino stands or
R¹³ and R¹⁴ together with the carbon atom to which they are attached represent cyclopropylidene, cyclobutylidene, cyclopentylidene or cyclohexylidene, or
R¹ and R² together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl, piperazinyl or succinimidyl which may be monosubstituted to trisubstituted by methyl,
R³ and R⁴ are identical or different and independently of one another for hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy, oxetan-3-yloxy, mercapto, methylthio, ethylthio, allylthio, propargylthio, benzylthio, cyclopentyl thio, phenyl, cyclohexylthio, cyclohexylthio, cyclohexylthylamyl Dimethylamino, phenylamino or pyrrolyl, piperidyl, morpholinyl or piperazinyl which are bonded via a nitrogen atom and in each case optionally monosubstituted to trisubstituted by methyl and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio.

These residual definitions can be given among themselves, that is, between the specified ones areas of preferred connections can be combined as desired.

Compounds which can preferably be used are also addition products of acids and those aminophthalic acid derivatives of the formula (I) in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, Q¹ and Q² have those meanings which are as for these radicals were preferred.

The acids that can be added preferably include halogen seric acids, such as. B. the hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, also phosphoric acid, sulfuric acid, Nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids,  such as B. acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, Citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids, such as e.g. B. p-toluenesulfonic acid, 1,5-naphthalenedisulfonic acid, saccharin and thio saccharin.

The present application also relates to new aminophthalic acid derivatives of the general formula (I-a),

in which
R¹⁷ and R¹⁸ are the same or different and are independently hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy or

stand where
R¹⁹ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R²⁰ represents hydrogen or alkyl, or
R¹⁹ and R²⁰ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl,
being the connections
3-aminophthalic acid dimethyl ester,
3-aminophthalic acid diethyl ester,
3-aminophthalic acid di-n-propyl ester,
3-aminophthalic acid 1-methyl ester,
3-aminophthalic acid 2-methyl ester,
3-aminophthalic acid,
3-aminophthalamide,
2- (N-methyl-N-phenyl-carbamoyl) -6-amino-benzanilide,
1,2-bis (N-methyl-N-phenyl-carbamoyl) -3-amino-benzene and
2- (N-methyl-N-phenyl-carbamoyl) -3-carbomethoxy-aniline,
with exception of.

Preferred are new compounds of formula (Ia) in which
R¹⁷ and R¹⁸ are identical or different and independently of one another for hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms, Cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, or

stand where
R¹⁹ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl having 3 to 7 ring members,
R²⁰ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R¹⁹ and R²⁰ together with the nitrogen atom to which they are attached are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclyl with 3 to 7 members.

New compounds of the formula (Ia) in which
R¹⁷ and R¹⁸ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, Allyloxy, Propargyloxy, Benzyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclohexenyloxy, Phenoxy, Oxetan-3-yloxy, Amino, Methylamino, Ethylamino, Dimethylamino, Phenylamino or in each case bonded via a nitrogen atom, in each case optionally monosubstituted to trisubstituted by methyl, pyriperyl, Morpholinyl or piperazinyl are available.

The present application also relates to new aminophthalene acid derivatives of the general formula (I-b),

in which
R²¹ for hydrogen or the grouping

in which R²⁵ has the meaning given below,
R²² for grouping

stands in what
R²⁵ represents hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl or heterocyclyl,
R²³ and R²⁴ are the same or different and independently of one another are hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, where R²³ and R²⁴ are not simultaneously hydroxy and the compounds
3-acetylamino-phthalic acid dimethyl ester and
3-Acetylamino-phthalic acid 1-methyl ester are excluded.

Preferred are new compounds of the formula (Ib) in which
R²¹ for hydrogen or the grouping

stands,
wherein R²⁵ has the preferred meaning given below,
R²² for grouping

stands in what
R²⁵ for hydrogen, each optionally substituted by alkoxycarbonyl, alkylcarbonyl or carboxy-substituted alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or in each case optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen-substituted cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, aryl, arylalkyl or heterocyclyl with 3 to 7 ring members,
R²³ and R²⁴ are the same or different and independently of one another for hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenyl alkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, where R²³ and R²⁴ are not simultaneously hydroxy.

New compounds of the formula (Ib) in which
R²¹ for hydrogen or the grouping

stands,
wherein R²⁵ has the particularly preferred meaning given below,
R²² for grouping

stands in what
R²⁵ for hydrogen, each optionally substituted by methoxycarbonyl, ethoxycarbonyl, acetyl or carboxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1,3 -dien-1-yl or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, thienyl, furyl, pyrazolyl, pyridyl or 2,3-dihydro which are optionally monosubstituted to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine [1,4] oxathiin stands,
R²³ and R²⁴ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy or oxetan-3-yloxy, where R²³ and R²⁴ are not simultaneously hydroxy.

The present application also relates to new aminophthalic acid derivatives of the general formula (I-c),

in which
R²⁶ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R²⁷ represents hydrogen or alkyl, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached, stand for optionally substituted heterocyclyl and
R²⁸ and R²⁹ are the same or different and are independently hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy.

Preferred are new compounds of formula (Ic) in which
R²⁶ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, halo genalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R²⁷ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl with 3 to 7 ring members and
R²⁸ and R²⁹ are the same or different and independently of one another for hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenyl alkoxy with 1 to 12 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy or heterocyclyloxy with 3 to 7 ring members.

New compounds of the formula (Ic) in which
R²⁶ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or in each case optionally up to three times by fluorine, chlorine, bromine, iodine , Methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or difluorochloromethoxy, substituted phenyl, naphthyl, thienyl, pyridyl or furyl,
R²⁷ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl or piperazinyl which may be monosubstituted to trisubstituted by methyl and
R²⁸ and R²⁹ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy or oxetan-3-yloxy.

The present application also relates to new aminophthalene acid derivatives of the general formula (I-d),

in which
R³⁰ represents optionally substituted heterocyclyl and
R³¹ for hydroxy or

stands, where
R³² represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R³³ represents hydrogen or alkyl, or
R³² and R³³ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl.

Preferred are new compounds of the formula (Id) in which
R³⁰ for optionally single to triple by alkyl with 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen substituted heterocyclyl with 3 to 7 ring members and
R³¹ for hydroxy or

stands, where
R³² for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl having 3 to 7 ring members,
R³³ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R³² and R³³ together with the nitrogen atom to which they are attached are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclyl with 3 to 7 members.

New compounds of the formula (Id), in which
R³⁰ stands for thienyl, furyl, pyrazolyl, pyridyl or 2,3-dihydro [1,4] oxathiin which is optionally monosubstituted to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine and
R³¹ stands for hydroxy, amino, methylamino, ethylamino, dimethylamino, phenylamino or via a nitrogen atom, each optionally monosubstituted to trisubstituted by methyl pyrrolyl, piperidyl, morpholinyl or piperazinyl.

The present application also relates to new aminophthalic acid derivatives of the general formula (I-e),

in which
R³⁴ represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl,
R³⁵ represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl or heteroaryl,
R³⁶ represents hydrogen or alkyl, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl.

Preferred are new compounds of the formula (Ie) in which
R³⁴ for hydrogen, each optionally substituted by alkoxycarbonyl alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or each optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen-substituted cycloalkyl having 3 to 8 carbon atoms, cycloalkenyl having 3 to 8 carbon atoms, aryl or arylalkyl,
R³⁵ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms halogen alkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R³⁶ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached represent heterocyclyl with 3 to 7 ring members which are optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms.

New compounds of the formula (Ie) in which
R³⁴ for hydrogen, each optionally substituted by methoxycarbonyl or ethoxycarbonyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1,3-diene-1 -yl or in each case optionally up to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R³⁵ represents hydrogen, methyl, ethyl, phenyl, cyclopropyl or oxethan-3-yl,
R³⁶ represents hydrogen or methyl, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached are each optionally mono- to trisubstituted by methyl-substituted pyrrolyl, piperidyl, morpholinyl or piperazinyl.

The present application also relates to new aminophthalic acid derivatives of the general formula (I-f),

in which
R³⁷ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl and
R³⁸ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic, alkoxy or dialkylamino or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cycloalkylidene, and
R³⁹ and R⁴⁰ are the same or different and independently of one another for hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, mercapto, alkylthio, alkenylthio, alkynylthio, arylalkylthio, cycloalkylthio, cycloalkenylthio, arylalkylliothio, arylalkylylio,

stand where
R⁴¹ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R⁴² represents hydrogen or alkyl, or
R⁴¹ and R⁴² together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl.

New compounds of the formula (If) in which
R³⁷ represents hydrogen, alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, cycloalkenyl having 3 to 7 carbon atoms, each phenyl optionally monosubstituted to trisubstituted by alkyl, alkoxy, halogen, cyano or nitro, Naphthyl or heterocyclyl with 3 to 7 ring members and
R³⁸ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, phenyl, heterocyclyl with 3 to 7 ring members, alkoxy with 1 to 4 carbon atoms or dialkylamino each has 1 to 4 carbon atoms in the alkyl chains or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cycloalkylidene having 3 to 8 carbon atoms, and
R³⁹ and R⁴⁰ are the same or different and independently of one another for hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenyl alkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, mercapto, alkylthio with 1 to 4 carbon atoms, alkenylthio with 2 to 4 carbon atoms, alkynylthio with 2 to 4 carbon atoms, arylalkylthio with 1 to 4 carbon atoms in the alkyl part, cycloalkylthio with 3 to 7 carbon atoms, cycloalkenylthio with 3 to 7 carbon atoms, phenylthio, heterocyclylthio with 3 to 7 ring members or

stand where
R⁴¹ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally optionally up to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl having 3 to 7 ring members,
R⁴² represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R⁴¹ and R⁴² together with the nitrogen atom to which they are attached are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclyl with 3 to 7 members.

New compounds of the formula (If) in which
R³⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, methylphenyl, Fluorophenyl, chlorophenyl, bromophenyl, cyanophenyl, methoxyphenyl, nitrophenyl, thienyl, furyl, pyridyl or chloropyridyl and
R³⁸ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, s-, i- or t-butyl, vinyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, thienyl or pyridyl, methoxy, Ethoxy, dimethyl amino or diethylamino is or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cyclopentylidene or cyclohexylidene, and
R³⁹ and R⁴⁰ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy, oxetan-3-yloxy, mercapto, methylthio, ethylthio, allylthio, propargylthio, benzylthio, cyclopentylthio, cyclohexylamio, cyclohexylamio, cyclohexylamio, cyclohexylamio, cyclohexylamio Dimethylamino, phenylamino or pyrrolyl, piperidyl, morpholinyl or piperazinyl which are bonded via a nitrogen atom and in each case optionally monosubstituted to trisubstituted by methyl.

The compounds of formula (I-a) are obtained (process a) if Nitrophthalic acid derivatives of the formula (II)

in which
R¹⁷ and R¹⁸ have the meanings given above,
with a reducing agent, if appropriate in the presence of a diluent, and if appropriate in the presence of a catalyst.

Those used to carry out process a) as starting materials required nitrophthalic acid derivatives are generally defined by the formula (II). In this formula (II), R¹⁷ and R¹⁸ preferably or in particular have those gen meanings already in connection with the description of the he Compounds of the formula (I-a) according to the invention as preferred or as ins were particularly preferred for R¹⁷ and R¹⁸.

The starting materials of the formula (II) are known (compare, for example, Bull. Soc. Chim. Fr. (1968), 4947-53; Chem. Ber., (1902) 3872, Anal. Chem., (1994) 1302-1315) and / or can be prepared by processes known per se (see also the manufacturing examples).

As a reducing agent for carrying out process a) according to the invention all substances customary for such reactions can be used. Preferably be called: hydrogen, metals, such as zinc, iron or tin; or Salts such as tin (II) chloride, sodium dithionite or sodium hydro gene sulfide.

The compounds of formula (I-b) are obtained (process b) if Amino compounds of the formula (III)

in which
R²³ and R²⁴ have the meanings given above,
with an acid halide of the formula (IV)

in which
R²⁵ has the meaning given above and
X represents halogen,
or with an acid anhydride of the formula (V)

in which
R²⁵ has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor,
or if (process c) nitro compounds of the formula (VI)

in which
R²³ and R²⁴ have the meanings given above,
in the presence of an acid anhydride of the formula (V) with hydrogen, if appropriate in the presence of a diluent and in the presence of a catalyst.

Those used to carry out process b) according to the invention as starting materials required amino compounds are generally defined by the formula (III). In  of this formula (III), R²³ and R²⁴ preferably or in particular have those Meanings already in connection with the description of the Invention compounds of the formula (I-b) as preferred or as in particular be were preferably given for R²³ and R²⁴.

The starting materials of formula (III) are either known and can according to known processes can be obtained (see, for example, J. Heterocycl. Chem. (1973) 891-9, J. Amer. Chem. Soc., (1937) 2580-3, Justus Liebigs Ann. Chem., (1881) 246, J. Amer. Chem. Soc., (1909) 486, J. Med. Chem. (1988) 1466-1471, Chem. Ber., (1886), 166) or are compounds of the formula according to the invention (I-a) and can be prepared by process a).

Those used to carry out process b) according to the invention as starting materials Acid halides still required are generally defi by the formula (IV) kidney. In this formula (IV) R²⁵ preferably or in particular that Be interpretation that already in connection with the description of the invention ß Compounds of formula (I-b) as preferred or as particularly preferred was specified for R²⁵. X represents halogen, preferably chlorine.

The one for performing the method b) according to the invention alternatively as off Acid anhydrides that are still required are all by the formula (V) commonly defined. In this formula (V) R²⁵ preferably or in particular the meaning already in connection with the description of the he Compounds of the formula (I-b) according to the invention as preferred or as ins was particularly preferred for R²⁵.

The acid halides of formula (IV) and the acid anhydrides of formula (V) are known synthetic chemicals.

Those used to carry out process c) according to the invention as starting materials required nitro compounds are generally defined by the formula (VI). In of this formula (VI), R²³ and R²⁴ preferably or in particular have those Meanings already in connection with the description of the Invention compounds of the formula (I-b) as preferred or as in particular be were preferably given for R²³ and R²⁴.  

The starting materials of the formula (VI) are known and / or per se known methods can be produced (see, for example, Bull. Soc. Chim. Fr. (1968), 4947-53; Chem. Ber., (1902) 3872, JP 04182460).

The compounds of formula (I-c) are obtained (method d) if one Amino compounds of the formula (VII)

in which
R²⁸ and R²⁹ have the meanings given above,
with an isocyanate of formula (VIII)

R²⁶-N = C = O (VIII)

in which
R²⁶ has the meaning given above,
or with a carbamoyl chloride of formula (IX)

in which
R²⁶ and R²⁷ have the meanings given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Those used to carry out process d) according to the invention as starting materials required amino compounds are generally defined by the formula (VII). In of this formula (VII), R²⁸ and R²⁹ preferably or in particular those Meanings already in connection with the description of the Invention compounds of the formula (I-c) as preferred or as in particular be were preferably given for R²⁸ and R²⁹.

The starting materials of formula (VII) are either known and can according to known processes can be obtained (see, for example, J. Heterocycl. Chem. (1973) 891-9, J. Amer. Chem. Soc., (1937) 2580-3, Justus Liebigs Ann. Chem., (1881) 246, J. Amer. Chem. Soc., (1909) 486, J. Med. Chem. (1988) 1466-1471, Chem. Ber., (1886), 166) or are compounds of the formula according to the invention (I-a) and can be prepared by process a).

Those used to carry out process d) according to the invention as starting materials Formula (VIII) generally defines isocyanates which are furthermore required. In this formula (VIII) R²⁶ preferably or in particular that Be interpretation that already in connection with the description of the invention ß compounds of formula (I-c) as preferred or as particularly preferred was specified for R²⁶.

As an alternative to performing the method d) according to the invention Carbamoyl chlorides that are still needed are represented by the formula (XIX) generally defined. In this formula (IX), R²⁶ and R²⁷ preferably or especially those meanings that are already in connection with the Be writing the compounds of formula (I-c) according to the invention as preferred or have been given as being particularly preferred for R²⁶ and R²⁷.

The isocyanates of formula (VIII) and the acid anhydrides of formula (IX) are known synthetic chemicals.

The compounds of the formula (I-d) are obtained (process e) if Amino compounds of the formula (X)

in which
R³¹ has the meaning given above,
with an acid halide of the formula (XI)

in which
R³⁰ has the meaning given above and
Y represents halogen,
or with an acid anhydride of the formula (XII)

in which
R³⁰ has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Those used to carry out process e) as starting materials required amino compounds are generally defined by the formula (X). In  of this formula (X) R³¹ preferably or in particular has the meaning the already in connection with the description of the Ver Bonds of formula (I-d) as preferred or as particularly preferred for R³¹ was specified.

The starting materials of the formula (X) are a subset of those according to the invention Compounds of formula (I-a) and can be prepared by method a).

Those used to carry out process e) as starting materials Acid halides still required are generally defi by the formula (XI) kidney. In this formula (XI) R³⁰ preferably or in particular that Be interpretation that already in connection with the description of the invention ß compounds of formula (I-d) as preferred or as particularly preferred was specified for R³⁰. Y represents halogen, preferably chlorine.

The one for performing the method e) according to the invention alternatively as off Acid anhydrides that are still required are all represented by the formula (XII) commonly defined. In this formula (XII) R³⁰ preferably or in particular the meaning already in connection with the description of the he Compounds of the formula (I-d) according to the invention as preferred or as ins was given particularly preferred for R³⁰.

The acid halides of the formula (XI) and the acid anhydrides of the formula (XII) are known synthetic chemicals.

The compounds of formula (I-e) are obtained (process f) if one Amino compounds of the formula (XIII)

in which
R³⁵ and R³⁶ have the meanings given above,
with an acid halide of the formula (XIV)

in which
R³⁴ has the meaning given above and
Z represents halogen,
or with an acid anhydride of the formula (XV)

in which
R³⁴ has the meaning given above,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid acceptor.

Those used to carry out process f) according to the invention as starting materials required amino compounds are generally defined by the formula (XIII). In this formula (XIII) R³⁵ and R³⁶ preferably or in particular have those meanings already in connection with the description of the he Compounds of the formula (I-e) according to the invention as preferred or as ins were particularly preferred for R³⁵ and R³⁶.

The starting materials of the formula (XIII) are a subgroup of the inventions compounds of the formula (I-a) according to the invention and can be prepared by process a) getting produced.

Those used to carry out process f) according to the invention as starting materials Acid halides still required are generally defi by the formula (XIV)  kidney. In this formula (XIV) R³⁴ preferably or in particular has that Meaning already in connection with the description of the Invention compounds of the formula (I-e) as preferred or as in particular be was preferably given for R³⁴. Z represents halogen, preferably chlorine.

As an alternative, to carry out the method f) according to the invention Acid anhydrides that are still required are all represented by the formula (XV) commonly defined. In this formula (XV) R³⁴ preferably or in particular the meaning already in connection with the description of the he Compounds of the formula (I-e) according to the invention as preferred or as ins was given particularly preferred for R³⁴.

The acid halides of the formula (XIV) and the acid anhydrides of the formula (XV) are known synthetic chemicals.

The compounds of formula (I-f) are obtained (process g) if one Amino compounds of the formula (XVI)

in which
R³⁹ and R⁴⁰ have the meanings given above,
with a keto derivative of the formula (XVII)

in which
R³⁷ and R³⁸ have the meanings given above and
W¹ and W² represent alkoxy, or together represent a double bonded oxygen atom,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid catalyst.

Those used to carry out process g) according to the invention as starting materials required amino compounds are generally defined by the formula (XVI). In this formula (XVI) R³⁹ and R⁴⁰ preferably or in particular have those meanings already in connection with the description of the he Compounds of the formula (I-f) according to the invention as preferred or as ins were particularly preferred for R³⁹ and R⁴⁰.

The starting materials of the formula (XVI) are compounds of the invention Formula (I-a) and can be prepared by method a).

Those used to carry out process g) according to the invention as starting materials Formula (XVII) generally defines keto derivatives required further kidney. In this formula (XVII), R³⁷ and R³⁸ preferably or in particular those meanings that are already related to the description of the Compounds of formula (I-f) according to the invention as preferred or ins were particularly preferred for R³⁷ and R³⁸. W¹ and W² stand for Alkoxy, preferably for methoxy or ethoxy, or together for a double bound oxygen atom.

The keto derivatives of the formula (XVII) are known synthetic chemicals.

As a diluent for carrying out process a) according to the invention are preferably considered: esters, such as methyl acetate or acetic acid ethyl ester; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sek- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethy lenglycol monomethyl ether or diethylene glycol monoethyl ether; Water, brine solutions such as ammonium chloride solution, aqueous acids such as for example hydrochloric acid or acetic acid, and any mixtures of the above Diluent.  

As a diluent for carrying out processes b), d), e) and f) are all inert organic solvents. For this preferably include aliphatic, alicyclic or aromatic hydrocarbons substances such as petroleum ether, hexane, heptane, cyclohexane, methyl cyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetra chloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, Di isopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones, such as acetone, Butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethyl formamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or Hexamethylphosphoric triamide; Esters such as methyl acetate or acetic acid reethylester; Sulfoxides such as dimethyl sulfoxide; or sulfones, such as sulfolane.

As a diluent for carrying out process c) according to the invention are preferably considered: esters, such as methyl acetate or acetic acid ethyl ester; Alcohols, such as methanol, ethanol, n- or i-propanol, n-, i-, sek- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethy lenglycol monomethyl ether or diethylene glycol monoethyl ether; or organic Acids such as acetic acid.

As a diluent for carrying out process g) according to the invention all inert organic solvents are suitable. This includes preferably aliphatic, alicyclic or aromatic hydrocarbons, such as for example petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, Benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as for example chlorobenzene, dichlorobenzene, dichloromethane, chloroform, tetra chloromethane, dichloroethane or trichloroethane; Ethers, such as diethyl ether, Diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydro furan, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; Ketones, such as acetone, Butanone, methyl isobutyl ketone or cyclohexanone; Nitriles, such as acetonitrile, Propionitrile, n- or i-butyronitrile or benzonitrile; Amides such as N, N-dimethyl formamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or Hexamethylphosphoric triamide; Esters such as methyl acetate or acetic acid reethylester; Sulfoxides such as dimethyl sulfoxide; or sulfones, such as sulfolane.  

Process a) according to the invention is optionally carried out in the presence of a Catalyst carried out. Preferably all come for catalytic hydration metal preparations, such as Raney nickel, finely divided palladium or platinum, optionally on a support material, such as Activated carbon or calcium carbonate.

Come as a catalyst for carrying out process c) according to the invention all metal preparations customary for catalytic hydrogenations, such as for example Raney nickel, finely divided palladium or platinum, if appropriate on a carrier material, such as activated carbon or calcium carbonate.

Processes b), d), e) and f) according to the invention are optionally in In the presence of a suitable acid acceptor. As such, everyone comes usual inorganic or organic bases in question. These include preferential as alkaline earth metal or alkali metal hydroxides, carbonates or hydrogen car bonates, such as sodium hydroxide, potassium hydroxide, sodium carbonate, Potassium carbonate, potassium hydrogen carbonate or sodium hydrogen carbonate, as well tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethyl aniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N-methyl morpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyc ionone (DBN) or diazabicycloundecene (DBU).

Process g) according to the invention is optionally carried out in the presence of a acid catalyst performed. As such, all inorganic and or come ganic protonic and Lewis acids, as well as all polymeric acids. These include, for example, hydrogen chloride, sulfuric acid, phosphorus acid, formic acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, trifluoro methanesulfonic acid, toluenesulfonic acid, boron trifluoride (also as etherate), bortribro mid, aluminum trichloride, zinc chloride, ferric chloride, antimony pentachloride, acidic ion exchangers, acidic clays and acidic silica gel.

The reaction temperatures can be carried out when carrying out the inventive Processes a) to g) can be varied over a wide range. In general one works at temperatures from 0 ° C to 150 ° C, preferably at temperatures from 0 ° C to 80 ° C.  

To carry out the method a) for the preparation of the Ver Compounds of formula (I-a) are used per mole of the nitrophthalic acid derivative Formula (II) generally 1 to 15 moles, preferably 2 to 8 moles of Reducing agent.

To carry out process b) according to the invention for the preparation of the Ver Compounds of formula (I-b) are used per mole of the amino compound of the formula (III) in general 1 to 15 mol, preferably 2 to 8 mol of the acid halide Formula (IV) or acid anhydride of formula (V).

To carry out the process c) according to the invention for the preparation of the Ver Compounds of the formula (I-b) are used per mole of the nitro compound of the formula (VI) generally 1 to 15 moles, preferably 2 to 8 moles of the acid anhydride Formula (V) and 1 to 100 moles, preferably 1 to 50 moles of hydrogen.

To carry out the method d) for the preparation of the Ver Compounds of the formula (I-c) are used per mole of the amino compound of the formula (VII) generally 1 to 15 mol, preferably 2 to 8 mol, of the isocyanate Formula (VIII) or carbamoyl chloride of formula (IX).

To carry out the method e) for the preparation of the Ver Compounds of the formula (I-d) are used per mole of the amino compound of the formula (X) generally 1 to 15 mol, preferably 2 to 8 mol, of the acid halide Formula (XI) or acid anhydride of the formula (XII).

To carry out the method f) for the preparation of the Ver Compounds of the formula (I-e) are used per mole of the amino compound of the formula (XIII) generally 1 to 15 moles, preferably 2 to 8 moles of the acid halide Formula (XIV) or acid anhydride of formula (XV).

To carry out the process g) according to the invention for the preparation of the Ver Compounds of the formula (I-f) are used per mole of the amino compound of the formula (XVI) generally 1 to 15 moles, preferably 2 to 8 moles of keto compound of the formula (XIV) or acid anhydride of the formula (XV).  

All methods of the invention are generally under normal pressure carried out. However, it is also possible to increase or decrease it Pressure - generally between 0.1 bar and 10 bar - to work.

The active compounds according to the invention have a strong microbicidal action and can be useful to combat unwanted microorganisms be used. The active ingredients are for use as pesticides, particularly suitable as fungicides.

Fungicides in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Bactericidal agents are used in plant protection to combat Pseudomonada ceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae used.

Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
Xanthomonas species, such as, for example, Xanthomonas campestris pv. Oryzae;
Pseudomonas species, such as, for example, Pseudomonas syringae pv. Lachrymans;
Erwinia species, such as, for example, Erwinia amylovora;
Pythium species, such as, for example, Pythium ultimum;
Phytophthora species, such as, for example, Phytophthora infestans;
Pseudoperonospora species, such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
Plasmopara species, such as, for example, Plasmopara viticola;
Bremia species, such as, for example, Bremia lactucae;
Peronospora species, such as, for example, Peronospora pisi or P. brassicae;
Erysiphe species, such as, for example, Erysiphe graminis;
Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;
Podosphaera species, such as, for example, Podosphaera leucotricha;
Venturia species, such as, for example, Venturia inaequalis;
Pyrenophora species, such as, for example, Pyrenophora teres or P. graminea (conidial form: Drechslera, Syn: Helminthosporium);
Cochliobolus species, such as, for example, Cochliob olus sativus (conidial form: Drechslera, Syn: Helminthosporium);
Uromyces species, such as, for example, Uromyces appendiculatus;
Puccinia species, such as, for example, Puccinia recondita;
Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;
Tilletia species, such as, for example, Tilletia caries;
Ustilago species, such as, for example, Ustilago nuda or Ustilago avenae;
Pellicularia species, such as, for example, Pellicularia sasakii;
Pyricularia species, such as, for example, Pyricularia oryzae;
Fusarium species, such as, for example, Fusarium culmorum;
Botrytis species, such as, for example, Botrytis cinerea;
Septoria species, such as, for example, Septoria nodorum;
Leptosphaeria species, such as, for example, Leptosphaeria nodorum;
Cercospora species, such as, for example, Cercospora canescens;
Alternaria species, such as, for example, Alternaria brassicae;
Pseudocercosporella species, such as, for example, Pseudocercosporella herpotri choides.

The good plant tolerance of the active ingredients in the fight against Concentrations necessary for plant diseases allow treatment of above-ground parts of plants, planting and seeds, and the soil.

The active compounds according to the invention can be particularly successful to combat cereal diseases, such as against pseudo cercosporella species, or diseases in wine, fruit and vegetable growing, such as against Botrytis and Plasmopara species.

The active ingredients can depend on their respective physical and / or chemical properties converted into the usual formulations such as solutions, emulsions, suspensions, powders, foams, pastes, Granules, aerosols, very fine encapsulations in polymeric substances and in envelopes masses for seeds as well as ULV cold and warm mist formulations.

These formulations are prepared in a known manner, e.g. B. by Mixing the active ingredients with extenders, i.e. liquid solvents, under Pressurized liquefied gases and / or solid carriers, if necessary using surface-active agents, ie emulsifiers and / or  Dispersing agents and / or foaming agents. In case of use of water as an extender can e.g. B. also organic solvents as auxiliary solvents are used. Essentially come as liquid solvents lichen in question: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated Aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, Chlorethylene or methylene chloride, aliphatic hydrocarbons, such as cyclo hexane or paraffins, e.g. B. petroleum fractions, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl iso butyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. With liquefied gaseous extenders or carrier substances are meant those liquids which, under normal temperature temperature and under normal pressure are gaseous, for. B. aerosol propellants, such as Halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. As solid carriers are possible: e.g. B. natural stone powder, such as kaolins, Clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates. Possible solid carriers for granules are: B. broken and fractionated natural rocks such as calcite, marble, pumice, sepio lith, dolomite and synthetic granules from inorganic and organic Flours and granules made of organic material such as sawdust, coconut husks, corn cobs and tobacco stalks. As an emulsifier and / or foam generator Funds are possible: B. nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. 26720 00070 552 001000280000000200012000285912660900040 0002019623744 00004 26601 alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydroly sate. Possible dispersants are: B. lignin sulfite and Methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins, and synthetic Phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, Cobalt, molybdenum and zinc can be used.  

The formulations generally contain between 0.1 and 95 weight percent active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their form also mixed with known fungicides, bactericides, acaricides, Nematicides or insecticides can be used, e.g. B. the effect to broaden the spectrum or to prevent the development of resistance. In many In this case, synergistic effects are obtained, i. H. the effectiveness of the mixture is greater than the effectiveness of the individual components.

The following connections can be considered as mixed partners:
Fungicides:
Aldimorph, ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, Benodanil, Benomyl, Benzamacril, Benzamacryl-Isobutyl, Bialaphos, Binapacryl, Biphenyl, Bitertanol, Blasticdiin-S, Bromuconazol, Bupirimat, Buthiobat,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxanil, cyphodaminazol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, fenapanil, fenarimol, fenbuconazole, fenfuram, fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzon, fluazinam, flumetover, fluoromid, fluquinconazole, flurprimolol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusulfazolutol, flusulfazolutol, flusilazolutol, flusilazolutol, flusilazolutolol Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilate, Iminocta dinetriacetate, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Ziram as well
Dagger G,
OK-8705,
OK-8801,
2 ′, 6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,
2,6-dichloro-N- (4-trifluoromethylbenzyl) benzamide,
2-aminobutane,
2-phenylphenol (OPP),
8-hydroxyquinoline sulfate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
1- [1- [2 - [(2,4-dichlorophenyl) methoxy] phenyl] ethenyl] -1H-imidazole,
bis- (1-methylethyl) -3-methyl -4 - [(3-methylbenzoyl) oxy] -2,5-thiophene dicarboxylate,
2,6-dichloro-N - [[4- (trifluoromethyl) phenyl] methyl] benzamide,
(E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
O-methyl-S-phenyl-phenylpropylphosphoramidothioat,
N- (5-chloro-2-methylphenyl) -2-methoxy-N- (2-oxo-3-oxazolidinyl) -acetam-id,
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-1-yl) ethanone-O- (phenylmeth-yl) oxime,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-thienyl) acetamide,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride,
1- (3,5-dichlorophenyl) -3- (2-propenyl) -2,5-pyrrolidinedione,
1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol,
1 - [[2- (4-chlorophenyl) -3-phenyloxiranyl] methyl] -1H-1,2,4-triazole,
Methane tetrathiol, sodium salt,
2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole,
N- [3-chloro-4,5-bis (2-propynyloxy) phenyl] -N'-methoxy-methanimidamide, -
α- (5-methyl-1,3-dioxan-5-yl) -β [[4- (trifluoromethyl) phenyl] methylene] -1H-1,2,4-triazol-1-ethanol,
1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione,
N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-oxo-3-furanyl) acetamide,
3,4-dichloro-1- [4- (difluoromethoxy) phenyl] -1H-pyrrole-2,5-dione,
N- [2,2,2-trichloro-1 - [(chloroacetyl) amino] ethyl] benzamide,
N-formyl-N-hydroxy-DL-alanine, sodium salt,
N- (4-cyclohexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one,
2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) acetamide,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide,
Methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate,
3- [2- (4-chlorophenyl) -5-ethoxy-3-isoxazolidinyl] pyridine,
2 - [(1-methylethyl) sulfonyl] -5- (trichloromethyl) -1,3,4-thiadiazole,
spiro [2H] -1-benzopyran-2,1 ′ (3′H) -isobenzofuran] -3′-one,
Methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate,
Potassium hydrogen carbonate,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] methyl] -1H-imidazole,
1 - [(diiodomethyl) sulfonyl] -4-methyl-benzene,
2-bromo-2- (bromomethyl) pentandinitrile,
2 - [[6-Deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranos yl] amino] -4-methoxy-1H-pyrrolo [2,3-d ] pyrimidine-5-carbonitrile,
Methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5-carboxylate,
2-chloro-N- (2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl) -3-pyridinecarboxamide,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioat, -
α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,
3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,
2,6-dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
N- (6-methoxy) -3-pyridinyl) cyclopropanecarboxamide,
3,5-dichloro-N- [cyan [(1-methyl-2-propynyl) oxy] methyl] benzamide,
4-chloro-2-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-1-sulfona-mid,
8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1,4-dioxaspiro [4.5] decane-2-methanamine,
2,2-dichloro-N- [1- (4-chlorophenyl) ethyl] -1-ethyl-3-methyl-cyclopropanc-arboxamide,
N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexane carboxamide.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

The active compounds according to the invention can, as such, in the form of their trade usual formulations or the use forms prepared from them, such as ge ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, Dusts and granules can be used. The application happens in usual way, e.g. B. by pouring, spraying, spraying, scattering, Ver foaming, brushing, etc. It is also possible to use the active ingredients using the ultra-low-volume process apply or the drug preparation or the Inject active ingredient into the soil yourself. It can also be the seed of the Plants are treated.

When treating parts of plants, the active substance concentrations can be in the application forms can be varied in a larger area: generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.  

In the seed treatment, amounts of active ingredient are generally from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g.

When treating the soil, active ingredient concentrations are from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight at the site of action required.

Manufacturing examples Example 1) Procedure a)

A suspension of 4.0 g of 3-nitrophthalic acid-1-methyl ester-2-butyl ester (14 mmol) and 4.2 g of zinc dust in a mixture of 60 ml of water and 25 ml of tetrahydrofuran is added dropwise with stirring at 20 ° C. within 15 ml of concentrated hydrochloric acid for about 20 minutes and then stirring for a further 2 hours at 20 ° C. The pH of the reaction mixture is adjusted to 5-6 by adding sodium bicarbonate solution. The mixture is then extracted with ether, the organic phase washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel with ether.
2.9 g (82.4% of theory) of 1-methyl-2-butyl 3-aminophthalate are obtained as a light yellow oil with a refractive index of n = 1.5403

Production of the starting material

4.1 g (15 mmol) of 2-butyl 3-nitrophthalate and 2.2 g (18 mmol) of dimethylformamide dimethyl acetal are dissolved in 40 ml of toluene and stirred under reflux for 12 hours. The reaction solution is cooled, first washed with sodium hydrogen carbonate solution and then with water, dried over sodium sulfate and concentrated at 60 ° C. under reduced pressure.
3.9 g (92% of theory) of 3-nitrophthalic acid, 1-methyl ester, 2-butyl ester are obtained as a light yellow oil.
1 H-NMR (CDCl₃ / TMS): 3.95 ppm (s, 3H).

Production of the preliminary product

A solution of 12 g of 3-nitrophthalic anhydride (Org. Synth., Coll. Vol. I, 410 [1941]) (6.2 mmol) in 80 ml of n-butanol is heated to 100 ° C. for 7 hours with stirring. The solvent is distilled off at 60 ° C. under reduced pressure, the residue is stirred with petroleum ether. The product is suctioned off through a frit and dried in vacuo at 50 ° C.
14.6 g (88.1% of theory) of 2-butyl 3-nitrophthalate are obtained as colorless crystals with a melting point of 137 ° C.

Example 2 Procedure a)

16.0 g (0.049 mol) of 3-nitrophthalic acid dibutyl ester and 14.5 g of zinc dust are in a mixture of 220 ml of water and 85 ml of tetrahydrofuran. At 20 ° C 54 ml of concentrated hydrochloric acid are slowly added dropwise and the mixture is stirred for 2 hours 20 ° C. The reaction mixture is extracted with ether, the organic phase with Water added and with sodium bicarbonate solution to a pH of 6 set. The phases are separated, the organic phase with water washed, dried over sodium sulfate and concentrated under reduced pressure. The residue is chromato chromato on silica gel using cyclohexane / ethyl acetate (3: 1) 10.8 g (75.1% of theory) of 3-aminophthalic acid dibutyl ester are obtained as light yellow oil with a refractive index of n = 1.5251.  

Production of the starting material

10.4 g (0.049 mol) of 3-nitrophthalic acid and 25.0 g (0.123 mol) of dimethylformamide dibutylacetal are dissolved in 125 ml of toluene and stirred under reflux for 10 hours. After cooling, the reaction mixture is washed with water, the organic phase is separated off, dried over sodium sulfate and concentrated under reduced pressure. 15.1 g (95.5% of theory) of 3-nitrophthalic acid dibutyl ester are obtained as a light brown oil.
1 H-NMR [CDCl₃ / TMS]: 4.35 ppm (t, 2H), 4.43 ppm (t, 2H).

Example 3 Procedure a)

39.0 g (0.174 mol) of 3-nitrophthalic acid-2-methylamide and 5 g of Raney nickel are placed in 200 ml of methanol. At 50 ° C, hydrogen is injected at 40-50 bar over a period of 4 hours. After cooling, the reaction mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is taken up in tetrahydrofuran, an excess of ethereal hydrochloric acid is added, the crystallizing hydrochloride is filtered off with suction and dried at 50 ° C. under reduced pressure.
25.1 g (62.6% of theory) of 3-aminophthalic acid-2-methylamide hydrochloride are obtained.
1 H-NMR (D₂O / TMS): 2.60 ppm (3 H).

Production of the starting material

22.0 g of methylamine (35% strength aqueous solution) are added dropwise to 38.6 g (0.2 mol) of 3-nitrophthalic anhydride in 50 ml of water at 20 ° C. and stirring is continued at 70 ° C. for 6 hours. The precipitate that precipitates after cooling is filtered off and dried at 50 ° C. in vacuo.
39.0 g (87% of theory) of 3-nitrophthalic acid-2-methylamide are obtained.
1 H-NMR (DMSO / TMS): δ = 2.37 ppm.

Example 4 Procedure a)

130 g (0.58 mol) of 3-nitrophthalic acid 1-methyl ester (J. Amer. Chem. Soc., (1909) 486) are added with the addition of 10 g of Raney nickel at a temperature of 40 ° C. and a pressure of 50 bar catalytically reduced with hydrogen. The catalyst is filtered off and the filtrate is concentrated under reduced pressure. The residue is chromatographed on silica gel with ether.
25.2 g (22.3% of theory) of 1-methyl 3-aminophthalate are obtained as a light yellow oil.
1 H-NMR: 3.85 ppm (s [3H] / CDCl₃).

Production of the preliminary product

45.2 g (0.21 mol) of 3-nitrophthalic acid and 27 g of concentrated sulfuric acid are dissolved in 450 ml of methanol and stirred under reflux for 24 hours. After cooling, the mixture is poured into water with stirring. The precipitate is filtered off and dried at 50 ° C under reduced pressure.
39.0 g (82.5% of theory) of 3-nitrophthalic acid, 1-methyl ester, are obtained as colorless crystals with a melting point of 146 ° C. (Org. Synth., Coll. Vol. I, 408 [1941]).

Example 5 Procedure b)

In a solution of 2.1 g (8.4 mmol) of 3-aminophthalic acid 1-methyl ester-2-butyl ester and 0.84 g (8.4 mmol) of triethylamine in 40 ml of toluene, 0.66 g (8, Add 4 mmol of acetyl chloride, dissolved in 5 ml of toluene. After the addition has ended, the mixture is stirred at 50 ° C. for 2 hours. For working up, the mixture is cooled to 20 ° C., the reaction mixture is washed with water, the organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel with ether.
1.8 g (73.1% of theory) of 1-methyl-2-butyl 3-acetylaminophthalate are obtained as a colorless oil with a refractive index of n = 1.5273.

Example 6 Procedure c)

74 g (0.329 mol) of 3-nitrophthalic acid, 2-methyl ester and 150 ml of isobutyric acid anhydride are dissolved in 500 ml of methanol, and 8 g of palladium on activated carbon (5%) are added. At 20 ° C, hydrogen is injected at a pressure of 3-5 bar for 5 hours. The reaction mixture is let down, then filtered and the filtrate is concentrated under reduced pressure. The residue is recrystallized from diiso propyl ether.
53.8 g (61.6% of theory) of 3- (2-methylpropionylamino) phthalic acid 2-methyl ester are obtained, melting point 137-139 ° C.

Production of the starting material

26.0 g (0.135 mol) of nitrophthalic anhydride are dissolved in 200 ml of methanol and heated under reflux for 8 hours. The solvent is distilled off under reduced pressure and the residue is stirred with petroleum ether and then suction filtered. 28.8 g (95% of theory) of 3-nitrophthalic acid 2-methyl ester are obtained.
1 H-NMR [DMSO / TMS]: 3.85 ppm (s, 3H).

Example 7 Procedure d)

3.3 g (0.011 mol) of 3-aminophthalic acid dibutyl ester, 0.74 g (0.013 mol) of methyl Isocyanate and 0.3 ml triethylamine are dissolved in 30 ml toluene and 8 hours stirred at 60 ° C. After cooling, the reaction mixture with water washed, the organic phase separated, dried over sodium sulfate and concentrated under reduced pressure. The residue is mixed with ether on silica gel chromatographed. 2.3 g (59.7% of theory) of 3- (methylaminocarbonyl) are obtained amino) phthalic acid dibutyl ester with a refractive index of n = 1.5278.  

Example 8 Procedure e)

4.6 g (0.02 mol) of 3-aminophthalic acid-2-methylamide hydrochloride and 4.4 g (0.044 mol) of triethylamine are dissolved in 50 ml of acetonitrile. A solution of 3.5 g (0.02 mol) of 6-chloronicotinoyl chloride in 20 ml of acetonitrile is added dropwise at 20 ° C. The mixture is stirred at 20 ° C for 2 hours. The reaction mixture is mixed with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica gel using ethyl acetate.
4.35 g (65.2% of theory) of 3- (6-chloronicotinoylamino) phthalic acid 2-methylamide are obtained as a viscous oil.
1 H NMR (DMSO): 2.09 ppm (3H).

Example 9 Procedure f)

4.6 g (0.02 mol) of 3-aminophthalic acid-2-methylamide hydrochloride and 4.4 g (0.044 mol) of triethylamine are dissolved in 50 ml of acetonitrile. A solution of 2.2 g (0.021 mol) of isobutyric acid chloride in 10 ml of acetonitrile is added dropwise at 20 ° C. and stirring is continued at 20 ° C. for 2 hours. The reaction mixture is stirred with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and concentrated under reduced pressure.
2.1 g (39% of theory) of 3- (2-methylpropionylamino) phthalic acid-2-methylamide are obtained as a light yellow oil.
NMR (CDCl₃ / TMS): δ = 1.31; 1.34 ppm

Example 10 Procedure g)

3.9 g of 3-aminophthalic acid 1-methyl ester (20 mmol) and 2.4 g (22 mmol) of ortho-formic acid trimethyl ester are dissolved in 6.2 g (60 mmol) of acetic anhydride, heated to 140 ° C. with stirring and Stirred for 7 hours at this temperature. After cooling, water is added with vigorous stirring, and the precipitate that forms is filtered off with suction through a suction filter. The crude product is dissolved in chloroform, dried over sodium sulfate and concentrated under reduced pressure. The residue is stirred in diisopropyl ether, suction filtered and dried at 50 ° C. under reduced pressure.
3.1 g (65.4% of theory) of 3-methoxymethylidene aminophthalic acid dimethyl ester are obtained as colorless crystals.
1 H-NMR: 2.19 ppm (s, [3H] / CDCl₃)

Example 11 Procedure g)

5.0 g (0.024 mol) of dimethyl 3-aminophthalate (J. Amer. Chem. Soc., (1937) 2580-3), 6.7 g (0.048 mol) of 4-chlorobenzaldehyde and 0.5 g (0.0024 mol) of toluene sulfonic acid are dissolved in 100 ml of toluene and refluxed for 4 hours Boiling heated. Half is used for the azeotropic removal of water of reaction the solvent was distilled off within a further 4 hours. After this Cooling, the solution is washed with water and over sodium sulfate dried. The solvent is distilled off under reduced pressure and the Chromatograph the residue with cyclohexane / ethyl acetate (3: 1) on silica gel.  

4.4 g (55% of theory) of 3- (4-chlorobenzylideneamino) phthalic acid are obtained dimethyl ester as light yellow crystals with a melting point of 84-85 ° C.

Analogous to Examples 1-11, as well as according to the general descriptions of processes a) to g) were those listed in Table 1 below Receive connections.

Example A Plasmopara test (vines) / protective

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are used with the active ingredient preparation sprayed. After the spray coating has dried on, the plants are added an aqueous spore suspension of Plasmopara viticola inoculated and lead ben then 1 day in a humid chamber at 20 to 22 ° C and 100% relative air humidity. The plants are then 5 days in a greenhouse at 21 ° C. and about 90% humidity. The plants are then moistened and placed in a wet room for 1 day.

Evaluation is carried out 6 days after the inoculation.

In this test, e.g. B. the following compounds of the preparation examples (4), (6), (13) and (15) at an exemplary active ingredient concentration of 100 ppm an efficiency of up to 97% compared to the untreated control.  

Example B Botrytis test (bean) / protective

Solvent: 4.7 parts by weight of acetone
Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are treated with the active ingredient sprayed fabric preparation. After the spray coating has dried on each Leaf 2 small pieces of agar overgrown with Botrytis cinerea. The inoculated plants are in a darkened, humid chamber at 20 ° C set up. 3 days after the inoculation, the size of the infestation spots on the Scroll evaluated.

In this test, e.g. B. the following compounds of the preparation examples (4), (6), (13), (14), (15), (16) and (17) in an exemplary Active ingredient concentration of 100 ppm an efficiency up to 98%.  

Example C Pseudocercosporella herpotrichoides test (wheat) / protective

Solvent: 10 parts by weight of N-methyl-pyrrolidone
Emulsifier: 0.6 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amounts of solvent and emulsifier and dilute the concentrate with water to the desired concentration.

To test for protective effectiveness, young plants are sprayed with the Active ingredient preparation in the specified application rate.

After the spray coating has dried on, the plants are attached to the stem base Spores of Pseudocercosporella herpotrichoides inoculated.

The plants are grown in a greenhouse at a temperature of approx. 10 ° C and a relative humidity of approx. 80%.

Evaluation is carried out 21 days after the inoculation.

In this test, e.g. B. the following compounds (4) and (14) of Her position examples with an exemplary active ingredient concentration in the Spray liquor of 250 ppm efficiency of 100% compared to untreated control.  

Appendix: Procedure:

Claims (24)

1. Use of compounds of the formula (I), in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping stands,
where R¹¹ has the meaning given below,
R² is hydrogen or one of the following groups stands,
wherein
R⁸ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R⁹ represents hydrogen or alkyl, or
R⁸ and R⁹ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl,
R¹⁰ represents alkyl, alkenyl, alkynyl, cycloalkyl which is optionally monosubstituted to trisubstituted by aryl or cycloalkyl or heterocyclyl,
R¹¹ represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl or heterocyclyl,
R¹² is alkyl, aryl or heterocyclyl, or
R¹ and R² together for a grouping stand in what
R¹³ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl and
R¹⁴ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, alkoxy or dialkylamino or
R¹³ and R¹⁴ together with the carbon atom to which they are attached represent cycloalkylidene, or
R¹ and R² together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl,
R³ and R⁴ are the same or different and independently of one another for hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, mercapto, alkylthio, alkenylthio, alkynylthio, arylalkylthio, cycloalkylthio, cycloalkenylthio, aryllyloxythio, aryllyloxythio, or arylylthio, stand where
R¹⁵ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R¹⁶ represents hydrogen or alkyl, or
R¹⁵ and R¹⁶ together with the nitrogen atom to which they are bound, represent optionally substituted heterocyclyl and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, halogen, cyano, nitro, alkyl, alkoxy, alkylthio, haloalkyl, haloalkoxy or haloalkylthio,
to control pests. 2. Use of the compounds of formula (I) according to claim 1, in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping where R11 has the preferred meaning given below,
R² is hydrogen or one of the following groups stands in what
R⁸ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally optionally up to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R⁹ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R⁸ and R⁹ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl with 3 to 7 ring members,
R¹⁰ for optionally substituted by phenyl or cycloalkyl with 3 to 8 carbon atoms, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, alkynyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms or for heterocyclyl with 3 to 7 rings stands,
R¹¹ for hydrogen, in each case optionally substituted by alkoxy carbonyl, alkylcarbonyl or carboxy-substituted alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or in each case optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl with 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen substituted cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, aryl, arylalkyl or heterocyclyl with 3 to 7 ring members,
R¹² represents alkyl having 1 to 4 carbon atoms, phenyl, naphthyl or heterocyclyl having 3 to 7 ring members, or
R¹ and R² together for a grouping stand in what
R¹³ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, cycloalkenyl with 3 to 7 carbon atoms, each optionally phenyl substituted once to three times by alkyl, alkoxy, halogen, cyano or nitro , Naphthyl or heterocyclyl with 3 to 7 ring members and
R¹⁴ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, cycloalkenyl with 3 to 7 carbon atoms, phenyl, naphthyl, heterocyclyl with 3 to 7 ring members, alkoxy with 1 to 4 Carbon atoms or dialkylamino each having 1 to 4 carbon atoms in the alkyl moieties or
R¹³ and R¹⁴ together with the carbon atom to which they are bound, represent cycloalkylidene having 3 to 7 carbon atoms, or
R¹ and R² together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl with 3 to 7 ring members,
R³ and R⁴ are the same or different and independently of one another for hydroxyl, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cyclo alkenyloxy with 3 to 7 carbon atoms, phenoxy, hetero cyclyloxy with 3 to 7 ring members, mercapto, alkylthio with 1 to 4 carbon atoms, alkenylthio with 2 to 4 carbon atoms, alkynylthio with 2 to 4 carbon atoms, arylalkylthio with 1 to 4 carbon atoms in the alkyl part , Cycloalkylthio with 3 to 7 carbon atoms, cycloalkenylthio with 3 to 7 carbon atoms, phenylthio, heterocyclylthio with 3 to 7 ring members or stand where
R¹⁵ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally single to triple by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R¹⁶ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R¹⁵ and R¹⁶ together with the nitrogen atom to which they are bound, are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclicl having 3 to 7 ring members, and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, halogen, cyano, nitro, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkyl, haloalkoxy or halo genalkylthio each have 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms. 3. Use of the compounds of formula (I) according to claim 1, in which
Q¹ and Q² are the same or different and independently of one another represent oxygen or sulfur,
R1 for hydrogen or the grouping stands,
where R¹¹ has the particularly preferred meaning given below,
R² is hydrogen or one of the following groups stands in what
R⁸ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclo hexyl or each optionally up to three times by fluorine, chlorine, bromine, iodine , Methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or di fluorochloromethoxy, substituted phenyl, naphthyl, thienyl, pyridyl or furyl,
R⁹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or
R⁸ and R⁹ together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl or piperazinyl which may be monosubstituted to trisubstituted by methyl,
R¹⁰ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, benzyl, 1-phenylethyl, 2-phenylethyl, cyclohexylmethyl, allyl, propargyl, oxethan-3-yl,
R¹¹ for hydrogen, in each case optionally substituted by methoxy carbonyl, ethoxycarbonyl, acetyl or carboxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1, 3-dien-1-yl or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, thienyl, furyl, pyrazolyl, pyridyl or 2, which are monosubstituted to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine, 3-di hydro [1,4] oxathiin stands,
R¹² represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, phenyl, naphthyl, thienyl, furyl or pyridyl, or
R¹ and R² together for a grouping stand in what
R¹³ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, methylphenyl , Fluorophenyl, chlorophenyl, bromophenyl, cyanophenyl, methoxyphenyl, nitrophenyl, thienyl, furyl, pyridyl or chloropyridyl and
R¹⁴ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, thienyl, furyl or pyridyl, methoxy, Ethoxy, Dimethylamino, Diethylamino stands or
R¹³ and R¹⁴ together with the carbon atom to which they are bound, stand for cyclopropylidene, cyclobutylidene, cyclopentylidene or cyclohexylidene, or
R¹ and R² together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl, piperazinyl or succinimidyl which may be monosubstituted to trisubstituted by methyl,
R³ and R⁴ are identical or different and independently of one another for hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy, oxetan-3-yloxy, mercapto, methylthio, ethylthio, allyl thio, propargylthio, benzylthio, cyclopentylthio, phenyl, ethyl, cyclohexylamyl, cyclohexylamyl, cyclohexylamyl Dimethylamino, phenylamino or bound via a nitrogen atom, each optionally mono- to trisubstituted by methyl-substituted pyrrolyl, piperidyl, morpholinyl or piperazinyl and
R⁵, R⁶ and R⁷ are the same or different and are independently hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, methylthio, ethylthio, trifluoromethyl, trifluoromethoxy, difluoromethoxy, difluorochloromethoxy, trifluoromethylthio, difluoromethylthio, difluorochloromethylthio. 4. Compounds of the formula (Ia), in which
R¹⁷ and R¹⁸ are the same or different and are independently hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy or stand where
R¹⁹ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R²⁰ represents hydrogen or alkyl, or
R¹⁹ and R²⁰ together with the nitrogen atom to which they are bound represent optionally substituted heterocyclyl,
being the connections
3-aminophthalic acid dimethyl ester,
3-aminophthalic acid diethyl ester,
3-aminophthalic acid di-n-propyl ester,
3-aminophthalic acid 1-methyl ester,
3-aminophthalic acid 2-methyl ester,
3-aminophthalic acid,
3-aminophthalamide,
2- (N-methyl-N-phenyl-carbamoyl) -6-amino-benzanilide,
1,2-bis (N-methyl-N-phenyl-carbamoyl) -3-amino-benzene and
2- (N-methyl-N-phenyl-carbamoyl) -3-carbomethoxy-aniline,
with exception of. 5. Compounds of formula (Ia) according to claim 4, in which
R¹⁷ and R¹⁸ are the same or different and are independently hydroxyl, alkoxy having 1 to 12 carbon atoms, alkenyloxy having 2 to 12 carbon atoms, alkynyloxy having 2 to 12 carbon atoms, phenylalkoxy having 1 to 4 carbon atoms in the alkyl part, cycloalkoxy having 3 to 7 carbon atoms , Cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, or stand where
R¹⁹ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally single to triple by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R²⁰ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R¹⁹ and R²⁰ together with the nitrogen atom to which they are bound stand for hetero cyclyl with 3 to 7 ring members which are optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms. 6. Compounds of formula (Ia) according to claim 4, in which
R¹⁷ and R¹⁸ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy, oxetan-3-yloxy, amino, methylamino, ethylamino, dimethylamino, phenylamino or via a nitrogen atom, each optionally mono- to triple-substituted by methyl-substituted pyrrole Piperidyl, morpholinyl or piperazinyl are available. 7. Compounds of the formula (Ib), in which
R²¹ for hydrogen or the grouping in which R²⁵ has the meaning given below,
R²² for grouping stands in what
R²⁵ represents hydrogen or optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, arylalkyl or heterocyclyl,
R²³ and R²⁴ are the same or different and independently of one another are hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, where R²³ and R²⁴ are not simultaneously hydroxyl and the compounds
3-acetylamino-phthalic acid dimethyl ester and
3-Acetylamino-phthalic acid 1-methyl ester are excluded. 8. Compounds of formula (Ib) according to claim 7, in which
R²¹ for hydrogen or the grouping stands,
wherein R²⁵ has the preferred meaning given below,
R²² for grouping stands in what
R²⁵ for hydrogen, each optionally substituted by alkoxy carbonyl, alkylcarbonyl or carboxy-substituted alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or in each case optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl cycloalkyl having 3 to 8 carbon atoms, having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen, cycloalkenyl having 3 to 8 carbon atoms, aryl, arylalkyl or heterocyclyl having 3 to 7 ring members,
R²³ and R²⁴ are the same or different and independently of one another for hydroxyl, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cyclo alkenyloxy having 3 to 7 carbon atoms, phenoxy, hetero cyclyloxy having 3 to 7 ring members, where R²³ and R²⁴ are not simultaneously hydroxy. 9. Compounds of formula (Ib) according to claim 7, in which
R²¹ for hydrogen or the primer stands,
wherein R²⁵ has the particularly preferred meaning given below,
R²² for grouping stands in what
R²⁵ for hydrogen, each optionally substituted by methoxy carbonyl, ethoxycarbonyl, acetyl or carboxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1, 3-dien-1-yl or, if appropriate, cyclo propyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, benzyl, thienyl, furyl, pyrazolyl, pyridyl or 2, optionally mono- to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine , 3-di hydro [1,4] oxathiin stands,
R²³ and R²⁴ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy or oxetan-3-yloxy, where R²³ and R²⁴ are not simultaneously hydroxy. 10. Compounds of the formula (Ic), in which
R²⁶ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R²⁷ represents hydrogen or alkyl, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl and
R²⁸ and R²⁹ are the same or different and are independently hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy. 11. Compounds of formula (Ic) according to claim 10, in which
R²⁶ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R²⁷ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached are optionally substituted heterocyclyl with 3 to 7 rings and
R²⁸ and R²⁹ are the same or different and independently of one another for hydroxyl, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 12 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 carbon atoms , Cyclo alkenyloxy with 3 to 7 carbon atoms, phenoxy or hetero cyclyloxy with 3 to 7 ring members. 12. Compounds of formula (Ic) according to claim 10, in which
R²⁶ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or in each case optionally up to three times by fluorine, chlorine, bromine, iodine, Methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, difluoromethoxy or difluorochloromethoxy, substituted phenyl, naphthyl, thienyl, pyridyl or furyl,
R²⁷ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or
R²⁶ and R²⁷ together with the nitrogen atom to which they are attached represent pyrrolyl, piperidyl, morpholinyl or piperazinyl which may be monosubstituted to trisubstituted by methyl and
R²⁸ and R²⁹ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy or oxetan-3-yloxy. 13. Compounds of the formula (Id), in which
R³⁰ represents optionally substituted heterocyclyl and
R³¹ for hydroxy or stands, where
R³² represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R³³ represents hydrogen or alkyl, or
R³² and R³³ together with the nitrogen atom to which they are bound represent optionally substituted heterocyclyl. 14. Compounds of formula (Id) according to claim 13, in which
R³⁰ represents hetero cyclyl with 3 to 7 ring members which is optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen and
R³¹ for hydroxy or stands, where
R³² for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally single to triple by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R³³ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R³² and R³³ together with the nitrogen atom to which they are attached represent hetero cyclyl with 3 to 7 ring members which are optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms. 15. Compounds of formula (Id) according to claim 13, in which
R³⁰ stands for thienyl, furyl, pyrazolyl, pyridyl or 2,3-dihydro [1,4] oxathiin which is optionally monosubstituted to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine and
R³¹ is hydroxyl, amino, methylamino, ethylamino, dimethylamino, phenylamino or bound via a nitrogen atom, each optionally monosubstituted to trisubstituted by methyl pyrrolyl, piperidyl, morpholinyl or piperazinyl. 16. Compounds of the formula (Ie), in which
R³⁴ represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl,
R³⁵ represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl or heteroaryl,
R³⁶ represents hydrogen or alkyl, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached represent optionally substituted heterocyclyl. 17. Compounds of formula (Ie) according to claim 16, in which
R³⁴ for hydrogen, each optionally substituted by alkoxycarbonyl alkyl having 1 to 5 carbon atoms, alkenyl having 2 to 5 carbon atoms, alkynyl having 2 to 5 carbon atoms or in each case optionally up to three times by alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and 1 to 5 halogen atoms or halogen-substituted cycloalkyl having 3 to 8 carbon atoms, cycloalkenyl having 3 to 8 carbon atoms, aryl or arylalkyl,
R³⁵ for hydrogen, alkyl with 1 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, each optionally one to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R³⁶ represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached are optionally mono- to trisubstituted by alkyl having 1 to 4 carbon atoms, heterocyclyl with 3 to 7 members. 18. Compounds of formula (Ie) according to claim 16, in which
R³⁴ for hydrogen, each optionally substituted by methoxycarbonyl or ethoxycarbonyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, penta-1,3-diene-1 -yl or in each case optionally up to trisubstituted by methyl, ethyl, trifluoromethyl, fluorine, chlorine or bromine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or benzyl,
R³⁵ represents hydrogen, methyl, ethyl, phenyl, cyclopropyl or oxethan-3-yl,
R³⁶ represents hydrogen or methyl, or
R³⁵ and R³⁶ together with the nitrogen atom to which they are attached each represent optionally mono- to trisubstituted by methyl-substituted pyrrolyl, piperidyl, morpholinyl or piperazinyl. 19. Compounds of the formula (If), in which
R³⁷ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl and
R³⁸ represents hydrogen, alkyl, alkenyl, cycloalkyl, cycloalkenyl, aryl, heterocyclyl, alkoxy or dialkylamino or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cycloalkylidene, and
R³⁹ and R⁴⁰ are the same or different and independently of one another for hydroxy, alkoxy, alkenyloxy, alkynyloxy, arylalkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy, heterocyclyloxy, mercapto, alkylthio, alkenylthio, alkynylthio, arylalkylthio, cycloalkylthio, cycloalkenylthio, arylalkylliothio, arylalkylylio, stand where
R⁴¹ represents hydrogen, alkyl, cycloalkyl, in each case optionally substituted aryl or heteroaryl,
R⁴² represents hydrogen or alkyl, or
R⁴¹ and R⁴² together with the nitrogen atom to which they are bound, represent optionally substituted heterocyclyl. 20. Compounds of formula (If) according to claim 19, in which
R³⁷ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 7 carbon atoms, cycloalkenyl with 3 to 7 carbon atoms, each optionally optionally up to three times substituted by alkyl, alkoxy, halogen, cyano or nitro Phenyl, naphthyl or heterocyclyl with 3 to 7 ring members and
R³⁸ for hydrogen, alkyl with 1 to 4 carbon atoms, alkenyl with 2 to 4 carbon atoms, cycloalkyl with 3 to 8 carbon atoms, cycloalkenyl with 3 to 8 carbon atoms, phenyl, heterocyclyl with 3 to 7 ring members, alkoxy with 1 to 4 carbon atoms or Dialkylamino with 1 to 4 carbon atoms in the alkyl chains is or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cycloalkylidene having 3 to 8 carbon atoms, and
R³⁹ and R⁴⁰ are the same or different and are independently hydroxy, alkoxy with 1 to 12 carbon atoms, alkenyloxy with 2 to 12 carbon atoms, alkynyloxy with 2 to 12 carbon atoms, phenylalkoxy with 1 to 4 carbon atoms in the alkyl part, cycloalkoxy with 3 to 7 Carbon atoms, cycloalkenyloxy with 3 to 7 carbon atoms, phenoxy, heterocyclyloxy with 3 to 7 ring members, mercapto, alkylthio with 1 to 4 carbon atoms, alkenylthio with 2 to 4 carbon atoms, alkynylthio with 2 to 4 carbon atoms, arylalkylthio with 1 to 4 carbon atoms in the alkyl part, Cycloalkylthio with 3 to 7 carbon atoms, cyclo alkenylthio with 3 to 7 carbon atoms, phenylthio, hetero cyclylthio with 3 to 7 ring members or stand where
R⁴¹ represents hydrogen, alkyl having 1 to 4 carbon atoms, cycloalkyl having 3 to 8 carbon atoms, each optionally optionally up to three times by halogen, alkyl, alkoxy each having 1 to 4 carbon atoms, haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1-5 the same or different halogen atoms, substituted phenyl, naphthyl or heterocycyl with 3 to 7 ring members,
R⁴² represents hydrogen or alkyl having 1 to 4 carbon atoms, or
R⁴¹ and R⁴² together with the nitrogen atom to which they are bound stand for hetero cyclyl with 3 to 7 ring members which are optionally monosubstituted to trisubstituted by alkyl having 1 to 4 carbon atoms. 21. Compounds of formula (If) according to claim 19, in which
R³⁷ for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, vinyl, allyl, propargyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, methyl phenyl, fluorophenyl, chlorophenyl, bromophenyl, cyanophenyl, methoxyphenyl, nitrophenyl, thienyl, furyl, pyridyl or chloropyridyl and
R³⁸ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, s-, i- or t-butyl, vinyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, phenyl, thienyl or pyridyl, methoxy, Ethoxy, dimethylamino or diethylamino is or
R³⁷ and R³⁸ together with the carbon atom to which they are attached represent cyclopentylidene or cyclohexylidene, and
R³⁹ and R⁴⁰ are the same or different and are independently hydroxy, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, pentoxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy , Dodecyloxy, allyloxy, propargyloxy, benzyloxy, cyclopentyloxy, cyclohexyloxy, cyclohexenyloxy, phenoxy, oxetan-3-yloxy, mercapto, methylthio, ethylthio, allyl thio, propargylthio, benzylthio, cyclopentylthio, phenyl, ethyl, cyclohexylamyl, cyclohexylamyl, cyclohexylamyl Dimethylamino, phenylamino or via a nitrogen atom, each of which is optionally mono- to trisubstituted by methyl-substituted pyrrolyl, piperidyl, morpholinyl or piperazinyl. 22. Pesticides, characterized by a content of at least one compound of formula (I) according to claim 1. 23. A method for controlling pests, characterized in that compounds of formula (I) according to claim 1 on pests and / or let their living space take effect. 24. Process for the preparation of pesticides, thereby characterized in that compounds of the formula (I) according to the Claims 1 to 21 with extenders and / or surface-active agents mixed.