JP2003507360A - Aminosalicylic acid amides and their use for controlling plant harmful organisms - Google Patents

Abstract

  (57) [Summary] The present invention relates to known acylaminosalicylic acid amides and novel acylaminosalicylic amides, some processes for their preparation, and their use for controlling harmful organisms in plants, and novel intermediates. And a method for producing the intermediate product.

Description

Detailed Description of the Invention

The present invention relates to known acylaminosalicylamides and novel acylaminosalicylamides, processes for producing them and their use for controlling plant-damaging organisms, and It also relates to novel intermediates and methods for producing them.

[0002] Certain aminosalicylic amides and their bactericidal and fungicidal actions are already known (see, for example, WO 97-08135, WO 98-41513 or WO 99-27783). However, the activity of these prior art compounds is not entirely satisfactory in all fields of use, especially at low application rates and low concentrations.

[0003]   Now, the general formula (I)

[0004]

[Chemical 17]

[Wherein R ¹ represents hydrogen or alkyl, R ² represents hydrogen or alkyl, or R ³ represents a group

[0006]

[Chemical 18]

[Wherein A is oxygen, sulfur or-(N-R ⁹ )-(wherein R ⁹ represents hydrogen or alkyl, or R ⁶ and the nitrogen atom to which they are attached are To form an optionally substituted heterocyclic ring), R ⁴ represents hydrogen, optionally substituted alkyl or optionally substituted aryl, or R ² and R ⁴ are , R together with the atom to which they are attached form a heterocyclic ring, R ⁵ represents hydrogen or alkyl, or R ⁴ and R ⁵ together with the carbon atom to which they are attached To form a carbocyclic ring, R ⁶ represents hydrogen or optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl, R ⁷ represents hydrogen or alkyl and R ⁸ is hydrogen or Archi It represents and Z represents hydrogen or alkyl optionally substituted in each case, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl. ] Is represented. } Acylaminosalicylamides have been found to be suitable for controlling organisms that cause damage to plants and industrial materials. These organisms should be understood in particular as meaning microorganisms.

In the definition, hydrocarbon chains such as alkyl, alkylene, alkenyl or alkynyl are in each case straight or branched, including when attached to heteroatoms such as alkoxy, alkylthio or alkylamino. It will be what you did. Hydrocarbon chains having 1 to 6 carbon atoms are preferred, unless otherwise specified.

Halogen usually represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, especially fluorine or chlorine.

Aryl represents an aromatic monocyclic or polycyclic hydrocarbon ring, for example phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

Heterocyclyl is a saturated or unsaturated and aromatic ring having up to 8 ring members, where at least one ring member is a heteroatom, ie, an atom different from carbon. Represents a compound. If the ring contains more than one heteroatom, these atoms may be the same or different. Preferred heteroatoms are oxygen, nitrogen and sulfur. If the ring contains more than one oxygen atom, these oxygen atoms are not directly adjacent. If appropriate, the cyclic compound is joined with another carbocyclic or heterocyclic fused or bridged ring to form a polycyclic ring system. Monocyclic or bicyclic ring systems are preferred, especially monocyclic or bicyclic aromatic ring systems.

Cycloalkyl represents a saturated carbocyclic ring compound, which, where appropriate with other carbocyclic fused or bridged rings, forms a polycyclic ring system.

Cycloalkenyl is a carbocyclic cyclic compound containing at least one double bond and, where appropriate, forming a polycyclic ring system with other carbocyclic fused or bridged rings. Represents

Halogenalkoxy represents partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkoxy, the halogen atoms may be the same or different.

Preferred halogen atoms are fluorine or chlorine, especially fluorine. If the halogenoalkoxy has another substituent, the maximum possible number of halogen atoms is reduced to a different free valence. Hydrocarbon chains having 1 to 6 carbon atoms are preferred, unless otherwise specified.

Halogenalkyl represents a partially or fully halogenated alkyl. In the case of polyhalogenated halogenoalkyl, the halogen atoms may be the same or different. Preferred halogen atoms are fluorine or chlorine, especially fluorine. If the halogenoalkyl carries another substituent, the maximum possible number of halogen atoms is reduced to a different free valence. 1 if not specified otherwise
Hydrocarbon chains having 1 to 6 carbon atoms are preferred.

If appropriate, the compounds of formula (I) may be found in various possible isomeric forms, in particular stereoisomers,
For example, it exists as a mixture of E and Z isomers, threo and erythro isomers, and also optical isomers. The use of both the E and Z isomers, and also of the threo and erythro isomers and the optical isomers, and any mixtures of these isomers are claimed.

R ¹ represents hydrogen or methyl, R ² represents hydrogen or C ₁ -C ₄ alkyl, and R ³ is a group

[0019]

[Chemical 19]

[0020] [In the group, A is oxygen, sulfur or-(N-R⁹ )-(Where R⁹ Also hydrogen
Preferably represents alkyl having 1 to 4 carbon atoms, or R⁶ And those
Has 3 to 7 ring members together with the nitrogen atom to which C is attached, C ₁  -C_Four Form a heterocyclic ring optionally substituted with alkyl. ), R^Four Is hydrogen, or in each case 1 to 6 carbon atoms in the alkyl moiety.
Alkoxy having a child, alkylthio, alkoxycarbonyl or alkyl
Represents an alkyl, optionally substituted with carbonyloxy, or an aryl moiety
Is an arylcarbonyloxy optionally substituted with hydroxy, formyloxy
Represents an optionally substituted alkyl, or in each case an alkyl moiety
Having 1 to 6 carbon atoms per minute, and in each case also an aryl moiety
Or heterocyclyl, where the heterocyclyl moiety is optionally substituted.
Represents aryl, arylalkyl or heterocyclylalkyl, or R² And R^Four Is 3 to 6 ring structures together with the atoms to which they are attached.
Forming a heterocyclic ring having components R^Five Is hydrogen or C₁ -C_Four Represents alkyl, or R^Four And R^Five Is 3 to 6 together with the carbon atom to which they are attached
Forming a carbocyclic ring having ring members, R⁶ Is hydrogen or C₁ -C₁₂Alkyl; C₁ -C_Four Optionally with alkyl
Converted C₃ -C₇ Represents cycloalkyl or aryl; 1 in the alkyl moiety
Arylalkyl having from 6 to 6 carbon atoms; heterocyclyl; or
Heterocyclylalkyl having 1 to 6 carbon atoms in the alkyl moiety (these are
Each of the aryl or heterocyclyl moieties optionally substituted
There is. ), R⁷ Is hydrogen or C₁ -C_Four Represents alkyl, R⁸ Is hydrogen or C₁ -C_Four Represents alkyl, and Z is hydrogen or C₁ -C₁₂Alkyl or alkylcarbonyl; C₁ -C _Four  C optionally substituted with alkyl₃ -C₇ Cycloalkyl; or cyclo
Represents alkylcarbonyl, aryl, arylcarbonyl; 1 in the alkyl moiety
Arylalkyl having from 1 to 6 carbon atoms, arylalkylcarbonyl
Heterocyclyl, heterocyclylcarbonyl; 1 to 6 alkyl moieties
Heterocyclylalkyl or heterocyclylalkylcarc having a carbon atom
Bonyl, and each of these is an aryl moiety or heterocyclyl.
Part is optionally replaced. ] Preference is given to using compounds of the formula (I)

Preferred substituents for aryl or arylalkyl are listed below: Halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; 1 to 6 carbon atoms in each case Having in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulphonyl; having in each case 2 to 6 carbon atoms, in each case straight-chain or branched Branched alkenyl or alkenyloxy; in each case straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, Halogenoalkoxy, halogeno Rucylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl; in each case straight-chain or branched halogeno having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms Alkenyl or halogenoalkenyloxy; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy having 1 to 6 carbon atoms in the individual alkyl moieties , Alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl; in each case having 1 to 6 carbon atoms and in each case halogen; having 1 to 4 carbon atoms A straight chain or branched alkyl group;
And optionally mono-substituted with the same or different substituents selected from the group consisting of straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms. Or polysubstituted, in each case double-bonded alkylene or dioxyalkylene; and cycloalkyl having 3 to 6 carbon atoms; aryl and aryloxy.

Preferred substituents for heterocyclyl or heterocyclylalkyl are listed below: Halogen, amino, hydroxyl, oxo, in each case an alkyl, alkoxy having 1 to 6 carbon atoms in the individual alkyl moiety. , Alkylthio, alkylamino, dialkylamino.

R ¹ represents hydrogen or methyl, R ² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and R ³ is a group

[0024]

[Chemical 20]

[In the group, A is oxygen, sulfur or-(N-R ⁹ )-(wherein R ⁹ is hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s -Or t-butyl, or R ⁶ and the nitrogen atom to which they are attached are taken together to represent pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl or hexahydroazepinyl optionally substituted with methyl or ethyl. R ⁴ represents hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy optionally substituted with a hydroxyl, formyloxy, phenyl moiety. , Ethylcarbonyloxy, propylcarbonyloxy, pentylcarbonyl Represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted with oxy or hexylcarbonyloxy, or phenyl, benzyl, 1-phenethyl, 2-phenethyl Or represents indolylmethyl, each of which is optionally substituted at the phenyl or heterocyclyl moiety, or R ² and R ⁴ are taken together with the atom to which they are attached to a pyrrolidine ring. Or represents a piperidine ring, R ⁵ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or R ⁴ and R ⁵ are represents a cyclopropane ring, a cyclopentane or cyclohexane ring together with the carbon atom to which, R ⁶ is hydrogen, methyl, Chill, n- or i- propyl, n-, i-, s-
Or t-butyl, pentyl, hexyl, heptyl, octyl; represents cyclopentyl or cyclohexyl optionally substituted with methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or Phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl or morpholinylbutyl (each of which may be a phenyl or heterocyclyl moiety) Or methyl, ethyl or propyl substituted with pyrrolidonyl, R ⁷ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , R ⁸ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, represent s- or t- butyl, and Z is hydrogen, methyl, ethyl, n- or i- propyl, n -, I-, s- or t-butyl, pentyl, hexyl, heptyl, octyl, methylcarbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s
-Or t-butylcarbonyl, pentylcarbonyl, hexylcarbonyl,
Heptylcarbonyl, octylcarbonyl; methyl, ethyl, n- or i-
Represents cyclopentyl, cyclohexyl, cyclopentylcarbonyl or cyclohexylcarbonyl optionally substituted with propyl, n-, i-, s- or t-butyl, phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, Phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl, morpholinylbutyl, phenylcarbonyl, benzylcarbonyl, 1-phenethylcarbonyl, 2-phenethylcarbonyl, phenylcarbonylpropylcarbonyl, phenylcarbonylbutylcarbonyl, phenylcarbonylpentylcarbonyl Or phenylcarbonylhexylcarbonyl, pyrrolidinylcarbonyl, morpholinylcarbonyl, pyrrolidinyl It represents Rubo sulfonyl butylcarbonyl or morpholinylcarbonyl butylcarbonyl, and each of which is optionally substituted phenyl moiety or heterocyclyl moiety. It is particularly preferred to use a compound of formula (I)

Particularly preferred substituents for phenyl are listed below: Fluorine, chlorine, bromine, cyano, amino, hydroxyl, formyl, carboxyl,
Carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i.
-Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoro Methylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethyl Amino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methyls Honiruokishi, ethyl sulfonyloxy, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxy imino methyl, methoxyiminoethyl or ethoxy imino ethyl, trimethylene attached to the double in each case (propane-1,3-diyl),
Tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, each of which is the same or different from the group consisting of fluorine, chlorine, methyl, trifluoromethyl, ethyl, n- and i-propyl. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or phenoxy, which is mono- or tetra-substituted with a substituent.

Particularly preferred substituents for heterocyclyl or heterocyclylalkyl are listed below: Halogen, amino, hydroxyl, oxo, methyl, ethyl, n- or i-.
Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino , Dimethylamino or diethylamino.

[0028]   The present invention also provides the compound of general formula (Ia)

[0029]

[Chemical 21]

[In the formula, R ¹¹ represents hydrogen or alkyl, R ¹² represents hydrogen or alkyl, or R ¹³ is a group.

[0031]

[Chemical formula 22]

[Wherein A represents oxygen, sulfur or-(N-R ¹⁹ )-(wherein R ¹⁹ represents hydrogen or alkyl, or R ¹⁶ and a nitrogen atom to which they are bonded) Together to form an optionally substituted heterocyclic ring), R ¹⁴ represents hydrogen, optionally substituted alkyl or optionally substituted aryl, or R ¹² and R ¹⁴ Is together with the atom to which they are attached to form a heterocyclic ring, R ¹⁵ represents hydrogen or alkyl, or R ¹⁴ and R ¹⁵ are together with the carbon atom to which they are attached. is in the form a carbocyclic ring, R ¹⁶ represents hydrogen or alkyl optionally substituted in each case, cycloalkyl, aryl or heterocyclyl, R ¹⁷ represents hydrogen or alkyl, and R ¹⁸ Represents hydrogen or alkyl, Z ¹ represents hydrogen, or alkyl optionally substituted in each case, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl, R ²⁰ is hydrogen , Optionally substituted alkyl or optionally substituted aryl or hetaryl, or R ¹² and R ²⁰ together with the atom to which they are attached form a heterocyclic ring, R ²¹ Represents hydrogen or alkyl, or R ²⁰ and R ²¹ together with the carbon atom to which they are attached form a carbocyclic ring. ] Is represented. } The novel substituted acylamino salicylamides of

[0033]   Furthermore, the novel substituted acylaminosalicylamides of general formula (Ia) are a) General formula (II)

[0034]

[Chemical formula 23]

[Wherein each of R ¹² and R ¹³ is as defined above. ] In the presence of a diluent, if appropriate in the presence of an acid acceptor, and if appropriate in the presence of another reaction aid, of general formula (III)

[0036]

[Chemical formula 24]

Wherein R ¹¹ is as defined above and X ¹ represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy. ] Or with b) the general formula (IV)

[0038]

[Chemical 25]

[Wherein each of R ¹² and R ¹³ is as defined above. ] The nitrosalicylic amides of ## STR3 ## were obtained by reaction with formic acid, if appropriate in the presence of a catalyst and, if appropriate, another reaction auxiliary.

Finally, the novel acylaminosalicylamides of the general formula (Ia) have a strong activity against organisms which damage plants and industrial materials, in particular a very strong fungicidal action. It has been found. At constant concentrations and application, the active compounds according to the invention can be said to be active against pests against plants and pests against animals.

[0041]   Pests are to be understood as meaning in particular microorganisms.

If appropriate, the compounds of the present invention exist as a mixture of various possible isomeric forms, in particular stereoisomers, for example E and Z isomers, threo and erythro isomers, and also optical isomers and the like. The use of both the E and Z isomers, and also of the threo and erythro isomers and the optical isomers, and any mixtures of these isomers are claimed.

R ¹¹ represents hydrogen or methyl, R ¹² represents hydrogen or C ₁ -C ₄ alkyl and R ¹³ is a radical

[0044]

[Chemical formula 26]

[0045] [In the group, A is oxygen, sulfur or-(NR)¹⁹)-(Where R¹⁹Also hydrogen
Preferably represents alkyl having 1 to 4 carbon atoms, or R¹⁶And those
Has 3 to 7 ring members together with the nitrogen atom to which C is attached, C ₁  -C_Four Form a heterocyclic ring optionally substituted with alkyl. ), R¹⁴Represents hydrogen or in each case 1 to 6 carbons in the alkyl moiety.
Alkoxy, alkylthio, alkoxycarbonyl or ar having an elementary atom
Represents an alkyl, optionally substituted with kircarcarbonyloxy, or
Aryl moieties optionally substituted with hydroxyl, formyloxy
Represents alkyl optionally substituted with bonyloxy, or in each case
Having 1 to 6 carbon atoms in the alkyl moiety and in each case an ari
Aryl or heterocyclyl moieties optionally substituted aryl,
Represents telocyclyl, arylalkyl or heterocyclylalkyl, or
Is R¹²And R¹⁴Is 3 to 6 ring structures together with the atoms to which they are attached.
Forming a heterocyclic ring having components R¹⁵Is hydrogen or C₁ -C_Four Represents alkyl, or R¹⁴And R¹⁵Is 3 to 6 together with the carbon atom to which they are attached
Forming a carbocyclic ring having ring members, R¹⁶Is hydrogen or C₁ -C₁₂Alkyl; C₁ -C_Four Optionally with alkyl
Converted C₃ -C₇ Represents cycloalkyl, aryl; 1 to 1 in the alkyl moiety
Arylalkyl having 6 carbon atoms; Heterocyclyl; 1 in the alkyl moiety
Heterocyclylalkyl having from 6 to 6 carbon atoms, each of which is
The aryl or heterocyclyl moiety is optionally substituted. ) Table
C or substituted with pyrrolidonyl₁ -C_Four Represents alkyl, R¹⁷Is hydrogen or C₁ -C_Four Represents alkyl, and R¹⁸Is hydrogen or C₁ -C_Four Represents alkyl, Z¹ Is hydrogen or C₁ -C₁₂Alkyl or alkylcarbonyl; C₁ −
C_Four C optionally substituted with alkyl₃ -C₇ Cycloalkyl, or shiku
Represents an alkylcarbonyl, aryl, arylcarbonyl; in the alkyl part
Arylalkyl having 1 to 6 carbon atoms, arylalkylcarbonyl
He; heterocyclyl, heterocyclylcarbonyl; 1 to 6 in the alkyl moiety
Heterocyclylalkyl having one carbon atom or heterocyclylalkylalkyl
Represents a carbonyl, and each of these is an aryl moiety or heterocyclyl.
Part has been replaced in some cases, R²⁰Represents hydrogen, or the formyloxy, aryl moiety is optionally substituted.
The arylcarbonyloxy, or in each case the alkyl moiety
Alkoxy, alkylthio, alkoxycarbo having 1 to 6 carbon atoms
C optionally substituted with nyl or alkylcarbonyloxy₁ -C_Four 
Represents alkyl, or 2 to 6 in aryl, heterocyclyl, alkyl moieties
Arylalkyl having 1 carbon atom, or 1 to 6 in the alkyl moiety
Heterocyclylalkyl having carbon atoms of (each of which is an aryl moiety)
Alternatively, the heterocyclyl moiety is optionally substituted. ) Or
Represents a substituted benzyl, or R¹²And R²⁰Is 3 to 6 ring structures together with the atoms to which they are attached.
Forming a heterocyclic ring having components R^{twenty one}Is hydrogen or C₁ -C_Four Represents alkyl, or R²⁰And R^{twenty one}Is 3 to 6 together with the carbon atom to which they are attached
Form a carbocyclic ring with ring members. ] The novel compounds of general formula (Ia), which represent

Preferred substituents for aryl or arylalkyl are listed below: Halogen, cyano, amino, hydroxyl, formyl, carboxyl, carbamoyl, thiocarbamoyl; 1 to 6 carbon atoms in each case Having in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulphonyl; having in each case 2 to 6 carbon atoms, in each case straight-chain or branched Branched alkenyl or alkenyloxy; in each case straight-chain or branched halogenoalkyl having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, Halogenoalkoxy, halogeno Rucylthio, halogenoalkylsulfinyl or halogenoalkylsulfonyl; in each case straight-chain or branched halogeno having 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms Alkenyl or halogenoalkenyloxy; in each case straight-chain or branched alkylamino, dialkylamino, alkylcarbonyl, alkylcarbonyloxy having 1 to 6 carbon atoms in the individual alkyl moieties , Alkoxycarbonyl, alkylsulfonyloxy, hydroxyiminoalkyl or alkoxyiminoalkyl; each having 1 to 6 carbon atoms and halogen, 1 to 4
From straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms Alkylene or dioxyalkylene, in each case double-bonded, in each case optionally mono- or polysubstituted with identical or different substituents selected from the group; and 3 to 6 carbons Cycloalkyl, aryl and aryloxy having atoms.

Preferred substituents for heterocyclyl or heterocyclylalkyl are listed below: Halogen, amino, hydroxyl, oxo, in each case an alkyl, alkoxy having 1 to 6 carbon atoms in the individual alkyl moiety. , Alkylthio, alkylamino, dialkylamino.

According to the invention, in particular R ¹¹ represents hydrogen or methyl, R ¹² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and R 12 ¹³ is the base

[0049]

[Chemical 27]

[In the group, A is oxygen, sulfur or-(N-R ¹⁹ )-(wherein R ¹⁹ is hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- Or t
- represents either represents a butyl, or R ¹⁶ and pyrrolidinyl optionally substituted if they are taken together with the nitrogen atom bonded with methyl or ethyl, morpholinyl, piperidinyl, piperazinyl or hexahydroazepinyl. ),
R ¹⁴ represents hydrogen or phenylcarbonyloxy, optionally substituted with hydroxy, formyloxy, phenyl moieties, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propyl. Represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted with carbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy, or phenyl, benzyl, 1- Phenethyl, 2-phenethyl or indolylmethyl, each of which is optionally substituted at the phenyl or heterocyclyl moiety, or R ¹² and R ¹⁴ together with the atom to which they are attached. Na It represents a pyrrolidine ring or a piperidine ring Te, R ¹⁵ is hydrogen, methyl, ethyl, n- or i- propyl, n-, i-, s-
Or t-butyl, or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached represent a cyclopropane ring, cyclopentane or cyclohexane ring, R ¹⁶ is hydrogen, methyl, Ethyl, n- or i-propyl, n-, i-, s-
Or t-butyl, pentyl, hexyl, heptyl, octyl; represents cyclopentyl or cyclohexyl optionally substituted with methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or Phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl or morpholinylbutyl, each of which may have a phenyl or heterocyclyl moiety. Substituted, or pyrrolidonyl-substituted methyl, ethyl or propyl, R ¹⁷ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t. -Represents butyl , And R ¹⁸ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Z ¹ is hydrogen, methyl, ethyl, n- or i-propyl, n -, I-, s- or t-butyl, pentyl, hexyl, heptyl, octyl, methylcarbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s
-Or t-butylcarbonyl, pentylcarbonyl, hexylcarbonyl,
Heptylcarbonyl, octylcarbonyl; methyl, ethyl, n- or i-
Represents cyclopentyl, cyclohexyl, cyclopentylcarbonyl or cyclohexylcarbonyl optionally substituted with propyl, n-, i-, s- or t-butyl, phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, Phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl, morpholinylbutyl, phenylcarbonyl, benzylcarbonyl, 1-phenethylcarbonyl, 2-phenethylcarbonyl, phenylcarbonylpropylcarbonyl, phenylcarbonylbutylcarbonyl, phenylcarbonylpentylcarbonyl Or phenylcarbonylhexylcarbonyl, pyrrolidinylcarbonyl, morpholinylcarbonyl, pyrrolidinyl (Each of which. The phenyl moiety or heterocyclyl moiety is optionally substituted) Rubo sulfonyl butylcarbonyl or morpholinylcarbonyl butylcarbonyl represents, R ²⁰ represents hydrogen, formyloxy, when the phenyl moiety Phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy, optionally substituted with, methyl, ethyl , N- or i-propyl, n-, i-, s- or t-butyl, or phenyl, 1-phenethyl, 2-phenethyl or indolylmethyl ( Each et al., Or represents optionally substituted phenyl moiety or heterocyclyl moiety.), Or a substituted benzyl, or R ¹² and R ^20, together with the atoms to which they are attached Represents a pyrrolidine ring or piperidine ring, R ²¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or R ²⁰ and R ²¹ are Together with the carbon atoms to which it is attached, it represents a cyclopropane ring, a cyclopentane or a cyclohexane ring. ] The novel compound of formula (Ia) which represents

Particularly preferred substituents for phenyl are listed below: Fluorine, chlorine, bromine, cyano, amino, hydroxyl, formyl, carboxyl,
Carbamoyl, thiocarbamoyl, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i.
-Propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl, trifluoromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoro Methylthio, difluorochloromethylthio, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, acetylamino, formylamino, N-formyl-N-methylamino, methylamino, ethylamino, n- or i-propylamino, dimethyl Amino, diethylamino, acetyl, propionyl, acetyloxy, methoxycarbonyl, ethoxycarbonyl, methyls Honiruokishi, ethyl sulfonyloxy, hydroxyiminomethyl, hydroxyiminoethyl, methoxyiminomethyl, ethoxy imino methyl, methoxyiminoethyl or ethoxy imino ethyl, trimethylene attached to the double in each case (propane-1,3-diyl),
Tetramethylene (butane-1,4-diyl), methylenedioxy or ethylenedioxy, each of which includes fluorine, chlorine, methyl, trifluoromethyl,
Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl or phenoxy, mono- to tetra-substituted with identical or different substituents from the group consisting of ethyl, n- and i-propyl.

Particularly preferred substituents for heterocyclyl or heterocyclylalkyl are listed below: Halogen, amino, hydroxyl, oxo, methyl, ethyl, n- or i-.
Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino , Dimethylamino or diethylamino.

The definition of general or preferred radicals given above applies not only to the final product of formula (I), but also to the starting materials or intermediates required for the preparation in each case accordingly. Also applies.

The definitions of the particular radicals, which are given in the respective combinations of radicals or preferred combinations of radicals, are independent of one another and independently of the particular combinations of radicals mentioned, and may be different radicals as desired. Replaced with the basic definition of.

[0055]   Formula (II) provides the aminosalicyne required as a starting material for carrying out the process a) of the invention.
A general definition for luamides is given. In this formula (II), R¹²And R ¹³ Each of which has already been mentioned in connection with the description of the compounds of formula (I) according to the invention.
R which has the same meaning as and is preferred or particularly preferred¹²And R¹³Also means
Has the same meaning as already mentioned as preferred or particularly preferred.

Some of the starting materials of formula (II) are known (eg J. Heteroc.
ycl. Chem. (1971), 8 (6), 989-91).

[0057]   Formula (II-a)

[0058]

[Chemical 28]

Where R ¹² is as defined above and R ¹³ is a group

[0060]

[Chemical 29]

[0061] [In the group, A, R¹⁴, R¹⁵, R¹⁶, R¹⁷, R¹⁸, Z¹ And R^{twenty one}Each of the above
As defined, R^{twenty two}Is formyloxy, an aryl carbo optionally substituted aryl moiety.
Nyloxy or, in each case, 1 to 6 carbon atoms in the alkyl moiety
Having an alkoxy, alkylthio, alkoxycarbonyl or alkylcarb
C substituted with rubonyloxy₁ -C_Four Represents alkyl or unsubstituted C₂ -C _Four  Represents alkyl, aryl, heterosyryl, 2 to 6 in the alkyl moiety
1 to 6 carbon atoms in an arylalkyl or alkyl moiety having carbon atoms
Heterocyclylalkyl having an atom (each of these is an aryl moiety
Or heterocyclyl moieties are optionally substituted. ) Or a substitution
Or represents R^{twenty two}And R¹²Form a heterocyclic ring together with the atoms to which they are attached
, R^{twenty two}And R^{twenty one}Represents a carbocyclic ring together with the carbon atom to which they are attached.
Form. ] Represents } Aminosalicylamides are novel and part of the subject of the present application
.

R ¹² is as defined above and R ¹³ is a group

[0063]

[Chemical 30]

[Wherein each of A, R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Z ¹ and R ²¹ is as defined above, R ²² is a formyloxy or aryl moiety. Represents optionally substituted arylcarbonyloxy, C ₁ -C ₄ alkyl substituted in each case by alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy having 1 to 6 carbon atoms in the alkyl moiety. Or unsubstituted C ₂ -C ₄ alkyl, and aryl, heterocyclyl, arylalkyl having 2 to 6 carbon atoms in the alkyl moiety or heterocyclylalkyl having 1 to 6 carbon atoms in the alkyl moiety (these Each of which is optionally substituted with an aryl or heterocyclyl moiety). Represents a substituted benzyl, or R ²² and R ¹² together with the atom to which they are attached represent a pyrrolidine ring or a piperidine ring, or R ²² and R ²¹ are attached to them Together with the carbon atom, it represents a cyclopentane ring or a cyclohexane ring. ] The amino salicylamides of formula (II-a), which represents

R ¹² is as defined above and R ¹³ is a group

[0066]

[Chemical 31]

[Wherein each of A, R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Z ¹ and R ²¹ is as defined above, R ²² is a formyloxy or phenyl moiety. Is optionally substituted phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy,
Methyl, ethyl, n- or i-propyl, each substituted with propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy,
represents n-, i-, s- or t-butyl, or unsubstituted ethyl, n- or i
-Propyl, n-, i-, s- or t-butyl, phenyl, 1-phenethyl, 2-phenethyl or indolylmethyl, each of which is optionally substituted on the phenyl or heterocyclyl moiety. Or
Or represents a substituted benzyl, or R ²² and R ¹² together with the atom to which they are attached represent a pyrrolidine ring or a piperidine ring, or R ²² and R ²¹ are attached to them Together with the carbon atom, it represents a cyclopentane ring or a cyclohexane ring. ] The amino salicylamides of formula (II-a), which represents

Aminosalicylamides of formula (II-a) are suitable diluents, preferably esters such as methyl acetate or ethyl acetate; methanol, ethanol, n-
Or i-propanol, n-, i-, s- or tert-butanol,
Alcohols such as ethanediol, propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether; water, salt solutions such as ammonium chloride solution, acids such as hydrochloric acid or acetic acid, and the dilutions mentioned above. In the presence of any mixture of agents,
Also, where appropriate, in the presence of a catalyst on a support such as activated carbon, eg Raney nickel, palladium or platinum, the compound of general formula (IV-a)

[0069]

[Chemical 32]

[Wherein each of R ¹² and R ¹³ is as defined above. ] It is obtained by reacting nitrosalicylic amides of the above with hydrogen (method c).

[0071]   Formula (IV-a) provides the nitrosa required as a starting material for carrying out the process c) of the invention.
A general definition for lytylamides is given. In this formula (IV-a), R ¹² And R¹³Each of the above is related to the description of the compound of formula (II-a) according to the present invention.
R has the same meanings as those already mentioned and is preferred or particularly preferred.¹²Over
And R¹³Has the same meaning as previously mentioned as being preferred or particularly preferred.
.

Nitrosalicylamides of formula (IV-a) are novel and form part of the subject of the present application.

Nitrosalicylamides are suitable diluents, by way of example and by way of preference also, aliphatic, cycloaliphatic or aromatic hydrocarbons such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, Benzene, toluene, xylene or decalin; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl Ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole; ketones such as acetone, butanone, methylisobutylketone Ton or cyclohexanone; nitriles such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile; amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-
Methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate; sulfoxides such as dimethylsulfoxide; or phosphones, such as condensing agents, where appropriate, such as phosgene, An acyl halide forming agent such as phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphoryl chloride, or thionyl chloride; an anhydride forming agent,
For example, ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides such as N
, N'-dicyclohexylcarbodiimide (DCC), or other conventional condensing agent,
Suitable, for example, in the presence of phosphorus pentoxide, polyphosphoric acid, N, N'-carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ) or triphenylphosphine / carbon tetrachloride. Then acid acceptors, by way of example and by way of preference also, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as sodium hydride, sodium amide , Sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, bicarbonate Sodium Ammonium carbonate, or tertiary amines, such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline,
N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (D
ABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU) in the presence of 2-hydroxy-3-nitrobenzoic acid or 2-hydroxy-3-benzoyl chloride.

[0074]

[Chemical 33]

[Wherein each of R ¹² and R ¹³ is as defined above. ] It is obtained by reacting with an amine (method d).

The 2-hydroxy-3-nitrobenzoic acid and 2-hydroxy-3-nitrobenzoyl chloride required as starting materials for carrying out the process d) according to the invention are known.
(For example, J. Het. Chem., 1971, 8 (6), 889-891, J.
． Chem. Soc. , 1953, 2049, 2050 or US03527.
865).

Formula (V) gives a general definition for the amines which are additionally required as starting materials for carrying out the process d) according to the invention. In this formula (V), R ¹² and R ¹³ have the same meanings as already mentioned in connection with the description of the compounds of formula (I) according to the invention, and are preferred or particularly preferred R ¹² And R ^{13 have} the same meanings as already mentioned as being preferred or particularly preferred.

[0078]   Amines of formula (VII) are known reagents of organic chemistry.

Some of the compounds of formula (I) are known and they can be prepared by several known methods (Biochim. Biophys. Acta).
1993, 262-268).

Formula (III) provides a general definition for the acylating agents further required as starting materials for carrying out the process a) of the invention. In this formula (III), R ¹¹ has the same meaning as already mentioned in connection with the description of the compound of the formula (I) according to the present invention, and the meaning of R ¹¹ which is preferable or particularly preferable is also preferable. Or, it has the same meaning as already mentioned as being particularly preferable. X ¹ represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy, preferably chlorine, hydroxyl, methoxy, ethoxy or acetoxy.

[0081]   The acylating agent of general formula (III) is a known reagent of organic chemistry.

Formula (IV) provides a general definition for the nitrosalicylamides required as starting materials for carrying out the process b) according to the invention. In formula (IV), R ¹² and R ¹³ each have the same meanings as already mentioned in connection with the description of the compounds of formula (I) according to the invention, and are preferred or particularly preferred R ¹² and R ^13. The meaning of ¹³ is also the same as already mentioned as being preferred or particularly preferred.

Some of the starting materials of formula (IV) are known (eg J. Heteroc.
ycl. Chem. (1971), 8 (6), 989-991).

The nitrosalicylamides of formula (IV-a) already described above in connection with the description of the process c) according to the invention are new.

Suitable diluents for carrying out the process a) according to the invention are all inert organic solvents. Illustrative and preferred of these organic solvents include: aliphatic, cycloaliphatic or aromatic hydrocarbons such as petroleum ether, hexane, heptane,
Cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane, or trichloroethane; ethers such as diethyl ether, diisopropyl ether, methyl t -Butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, or anisole; 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 ethyl acetate; sulfoxides, such as dimethyl sulfoxide, or phosphonic acids, such as sulfolane.

If appropriate, the process a) according to the invention is carried out in the presence of a suitable acid acceptor. Suitable acid acceptors are all customary inorganic or organic bases. As these, preferably, alkaline earth metal or alkali metal hydroxides, acetates,
Carbonates or bicarbonates such as sodium hydroxide, potassium hydroxide, sodium acetate, potassium acetate, calcium acetate, sodium carbonate, potassium carbonate,
Potassium bicarbonate or sodium bicarbonate, and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethyl-benzylamine, pyridine, N-methylpiperidine, N
-Methylmorpholine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

If appropriate, the process b) according to the invention is carried out in the presence of a catalyst. Suitable catalysts are all the catalysts customarily used for hydrogenation. Examples which may be mentioned are, if appropriate, supports such as Raney nickel, palladium or platinum on activated carbon.

When carrying out the processes a) and b) according to the invention, the reaction temperatures can be varied within a relatively wide range. Generally, these methods involve temperatures between 0 ° C and 180 ° C, preferably 0 ° C.
Perform at a temperature of ~ 130 ° C.

In order to carry out the process a) according to the invention for preparing a compound of formula (I), a compound of formula (II
1) to 2000 mol, preferably 1 mol, per mol of aminosalicylamide.
~ 800 mol of the acylating agent of formula (III) is used.

In order to carry out the process b) according to the invention for preparing a compound of formula (I), a compound of formula (IV
The amount of formic acid used is usually 100 to 2000 mol, preferably 200 to 1000 mol, per mol of the nitrosalicylic amide of a).

These methods of the present invention are usually carried out under atmospheric pressure. However, it is also possible to work under elevated or reduced pressure-typically from 0.1 bar to 10 bar.

The compounds of the present invention have strong microbicidal activity and can be used for controlling unwanted microorganisms such as fungi, molds and bacteria in crop protection and material protection.

A fungicide is used for protecting crops from Plasmodiophoromycetes (Pla).
smodiophoromycetes), oomycetes, Chitridiomycetes, zygomycetes (Zygo)
mycetes), Ascomycetes, Basidiomycetes (Basi)
It is used for controlling diomycetes) and imperfect fungi (Deuteromycetes).

Bactericides are used in the protection of Pseudomonas (Pseudomoaceae) in protecting crops.
nadaceae), Rhizobiaceae, Enterobacteriaceae (E
nterobacteriaceae, Corynebacterium (Coryneb)
and the family Streptomyces.
aceae).

Some non-limiting examples of pathogens causing fungal, fungal and bacterial diseases included in the above generic name are: Xanthomonas spp.
homonas campestris pv. oryzae); Pseudomonas species, for example, bacterial spot fungus (Pseu)
domonas syringae pv. lacrymans; Erwinia species, such as bacterial wilt (Erwinia a)
Pythium species, for example, Pythium ul.
phytophthora species, such as Phytoph.
thora infestans; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseud.
operonospora cubensis; Plasmopara species such as downy mildew (Plasmopa)
raviticola); Bremia species, such as lettuce downy mildew (Bremia lact)
Ucae); Peronospora species, such as downy mildew (Peronospo)
ra pisi or P. brassicae; Erysiphe species, such as powdery mildew (Erysiphe)
graminis); Sphaerotheca species, such as powdery mildew (Sph)
aerotheca fuliginea); Podosphaera species such as powdery mildew (Podos)
phaera leucotricha); Venturia species, such as the scab (Venturia i.
naequalis; Pyrenophora species, for example Pyrenophora
ora teres or P. graminea) (conidia): Dre
chslera, synonymous: Helminthosporium); Cochliobolus spp., for example, leaf spot fungus (Cochl)
iobolus sativus (conidiosporia type: Drechslera, synonyms: Helminthosporium);
Pendiculatus; Puccinia species, for example, Puccinia re
condita); Sclerotinia spp., for example, Sclerotial fungus (Sclero)
tinia sclerotiorum; Species of the genus Funtilus (Tilletia), for example, the nettle smut (Tillet
ia carriers); smut (Ustilago) species, for example, Ustilago nud
a or Ustilago avenae); Pellicularia species, for example, Bacterial wilt disease (Pelli)
Cularia sasakii); Pyricularia species, such as blast fungus (Pyric)
ularia oryzae); Fusarium species, such as Fusarium fusarium
culmorum); Botrytis species, for example Botrytis
Cinerea); Septoria species, such as Bacterial wilt (Septria no)
dorum); Leptosphaeria species, such as wheat wilt fungus
(Leptosphaeria nodorum); Cercospora species, for example, Cercospora
Ra canescens; Alternaria species, for example, Black spot fungus (Alterna)
ria brassicae); Pseudocercosporella spp., for example, wheat eye blight fungus (Pseudocercosporella herpotr)
ichoides).

The fact that the active compounds are well tolerated by plants in the concentrations necessary to control plant diseases allow the treatment of above-ground parts of plants, growing stalks and seeds, and soil. .

The active compound of the present invention is, for example, a bacterium of the genus Botrytis (Botrytis spec.
ies), Phytophthora species and Plasmopara species (Plasmopara species) against fruit and vegetable cultivation and vine cultivation, or rice diseases, such as Pyricularia species (Pyrricularia species). It can be used particularly successfully for control.

According to the invention, it is possible to treat all plants and all parts of plants.
With regard to plants, it is to be understood here that all plants and plant populations, such as desirable and undesired wild plants or cultivated plants (including naturally occurring cultivated plants), are meant. Cultivated plants include conventional breeding and optimization methods or biotechnological and genetic engineering techniques, including transformed plants and cultivated varieties that may or may not be protected by the plant grower's certificate. It can be a plant obtainable by a method or a combination of these methods. Part of a plant is to be understood as meaning all above and below ground parts and plant organs, such as shoots, leaves, flowers and roots, for example leaves, needles, stems, stems, flowers, Fruit bodies, fruits and seeds, as well as roots, tubers and rhizomes. Part of the plant also includes harvested plants and vegetative and reproductive material such as seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and plant parts with the active compounds according to the invention is carried out according to the customary treatment methods, for example by dipping, spraying, evaporation, atomizing.
ing), spraying, coating, and, in the case of propagation material, especially seeds, by further single-layer or multi-layer coating, either directly or with treatment to their environment, native or storage area. To do.

[0100]   Diseases of cereals are similarly successfully controlled.

The active compounds according to the invention are also suitable for increasing the yield of crops. Moreover, their active compounds show low toxicity and are well tolerated by plants.

The active compounds are, depending on their unique physical and / or chemical properties,
Customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, and microcapsules in polymeric substances and microcapsules in coating compositions for seeds and ULV cold mist. And warm mist formulations.

These formulations are prepared in a known manner, for example optionally with surfactants, ie
Emulsifiers and / or dispersants and / or foam formers are used to prepare the active compounds in admixture with fillers, ie liquid solvents, liquefied gases under pressure, and / or solid carriers. When the extender used is water, for example, an organic solvent can be used as an auxiliary solvent. Essentially, the following are suitable for use as liquid solvents: aromatic compounds such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic compounds such as chlorobenzenes, chloroethylenes or methylene chloride or chlorine. Cycloaliphatic hydrocarbons; cyclohexane or paraffins, for example, petroleum fractions and other aliphatic hydrocarbons; butanol, glycols and other alcohols and their ethers and esters, acetone, methyl ethyl ketone,
Ketones such as methyl isobutyl ketone or cyclohexanone; strong polar solvents such as dimethylformamide or dimethyl sulfoxide, or water unless otherwise specified. Liquefied gas extenders or carriers are liquids that are gaseous at room temperature and atmospheric pressure, for example, aerosol propellants such as halogenated hydrocarbons, or other butane, propane,
It should be taken to mean nitrogen and carbon dioxide. Suitable solid carriers are, for example, ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silica, alumina and silicates. . Suitable solid carriers for granules include, for example, calcite, marble, pumice, sepiolite and dolomite, such as ground and fractionated natural rock, or else synthetic granules consisting of inorganic and organic coarse powders, And sawdust,
It is a granular material composed of organic substances such as coconut kernels, corn cobs and tobacco stems. Suitable emulsifiers and / or foam-forming agents include nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers,
Alkyl sulfonates, alkyl sulfates, aryl sulfonates, or other protein hydrolysates. Suitable dispersants are, for example, lignin-sulfite waste liquors and methylcellulose.

Carboxymethyl cellulose; and natural and synthetic polymers in the form of powder, granules or latex such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids. Adhesives can be used in the formulation. Furthermore, mineral oils and vegetable oils can be used as additives.

Inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace amounts of iron, manganese, boron, copper, cobalt, molybdenum and zinc salts and the like. Element (trace n
A colorant such as turients) can be used.

The formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
Contains% by weight of active compound.

The active compound of the present invention is used as it is, or in order to broaden the range of action or prevent the development of resistance, for example, known fungicides, bactericides, acaricides and nematicides. It can be used as a formulation thereof mixed with an agent or an insecticide. In many cases synergistic effects are achieved, ie the activity of the mixture exceeds that of the individual components.

Examples of co-ingredients in the mixture are the following compounds: Fungicides: aldimorph, ampropylf.
os), ampropyl phospotassium (amplophilfos potas)
sium, andoprim, anilazine (anilazi)
ne), azaconazole, azoxystrobin (a)
zoxystrobin, benalaxyl, benodanil, benomyl, benzamacryl, benzacmacryl-isobutyl,
Bialaphos, binapacryl,
Biphenyl, bitatanol, blasticidin-S, bromconazole (bro)
muconazole), bupirimate, buthiobate, calcium polysulfide, capsimicin, carboxy, captafol, captanfol, captan, cartan, captan. carvon), quinomethionate (qui)
nomethionate), chlobenthiazo
ne), chlorphenazole, chloroneb (c)
hloroneb), chloropicrin, chlorothalonil, chlorzolinate.
nate), Clozylacon, Kufraneb (cufra)
neb), cymoxanil, cyproconazole (cypr)
oconazole), cyprodinil, cyprofuram, debacarb, dichlorophen
), Diclobutrazole, diclofluanid, diclomezine,
Dichloran, Diethofenc
arb), difenoconazole, dimethirimol, dimethomorph.
), Diniconazole, diniconazole-M (di)
Niconazole-M), dinocap, diphenylamine, dipyrithione.
, Ditalimfos, dithianon
, Dodemorph, dodine, drazoxolone, edifenphos, epoxiconazole (epoxic)
onazole), etaconazole, etirimol
(Ethirimol), etridiazole, famoxadon, fenapanil
, Fenarimol, fenbuconazole (fenbuco)
nasole, fenfuram, fenitropan (fen)
tropan), fenpiclonil, fenpropidin, fenpropimorph
orph), fentin acetate, fentin hydroxide, ferbam (fer)
bam), ferrimzone (fluimzone), fluazinam (fluaz)
inam), flumethover, fluoromide (fluo)
romide), fluquinconazole, flurprimidol, flucirazole (flusi)
lazole), flusulfamide, flutolanil, flutriafol, folpet, fosetyl-alumini.
, fosetyl-sodium, phthalide, fuberidazole, furalaxyl, furamethpyr, furcarbonyl, furcarbonil, furcarnafil.
le), fluconazole-cis, furmecyclox, guazatine, hexachlorobenzene, hexaconazole, hexexazole.
, Imazalil, imibenconazole (imibencon)
azole), iminoctadine, iminoctadine albesilate, iminoctadine triacetate
e), iodocarb, ipconazol
le), iprobenphos (IBP), iprodione (
iprodione), irumamycin, isoprothiolane, isovaleredin.
ione), kasugamycin, kresoxime-methyl (kres)
oxim-methyl), copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate,
Copper oxides, oxine copper, and copper preparations such as Bordeaux mixture, mancopper, mancozeb, maneb, meferimzone, mepanimipril (mepanimropyrim) Metalaxyl, metconazole, metasulfocarb, metofloxam
uroxam, metiram, metomecrum
lam), metsulfovax, mildiomycin, microbutanil
, Microzoline, nickel dimethyldithiocarbamate (nickel dimethyl)
biocarbamate), nitrosal-isopropyl (nitrothal)
-Isopropyl), nuarimol, offrace, oxadixyl, oxamocarb, oxolinic acid
, Oxycarboxim (oxycarboxim), oxyphenthiine (ox
yfenthin), paclobutrazole, pefurazoate (pe)
furazoate), penconazole (penconazole), pencycuron (pencycuron), Hosujifen (phosdiphen), pimaricin (pimaricin), Piperarin (piperalin), polyoxin (polyoxin), polyoxorim (polyoxorim), probenazole (probenazole), Purokuroratsu (prochloraz)
, Procymidone, Propamocarb
carb), propanosin-sodium (propanosine-sodium)
), Propiconazole, propineb (prop)
ineb), pyrazophos, pyriphenox (pyr)
ifenox), pyrimethanil (pyrimethanil), pyroquilon (
Pyroquilon, Pyroxyfur, Quinconazole, Quinoxyphen
oxyfen), quintozene (PCNB), sulfur and sulfur preparations, tebuconazole, tecloftalum (teclof)
talam), technazene, tetcyclasis (tetc)
cyclas), tetraconazole, thiabendazole, thicyophen
n), thifluzamide, thiophanate-methyl
(Thiophanate-methyl), thiram, thioximide, tolclofos-m.
Ethyl), tolylfluanid, triadimefon, triadimenol
, Triazbutil, triazoxide (triazox)
ide), trichlamide, tricyclazole (tr)
icyclazole), tridemorph, triflumizole, triforine,
Triticonazole, uniconazole, validamycin A, vinclozolin
Clozolin, viniconazole, zalilamide, zineb, ziram
am), and also Dagger G, OK-8705, OK-8801, α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,
2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -β-fluoro-β-propyl-1H-1,
2,4-triazole-1-ethanol, α- (2,4-dichlorophenyl) -β-methoxy-α-methyl-1H-1,2
, 4-triazole-1-ethanol, α- (5-methyl-1,3-dioxan-5-yl) -β-[[4- (trifluoromethyl) -phenyl] -methylene] -1H-1,2. , 4-triazole-1
-Ethanol, (5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5-
(1H-1,2,4-triazol-1-yl) -3-octanone, (E) -α- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide, 1-isopropyl {2-methyl- 1-[[[1- (4-methylphenyl) -ethyl] -amino] -carbonyl] -propyl} -carbamate, 1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazole −
1-yl) -ethanone O- (phenylmethyl) -oxime, 1- (2-methyl-1-naphthalenyl) -1H-pyrrole-2,5-dione, 1- (3,5-dichlorophenyl) -3- ( 2-propenyl) -2,5-pyrrolidinedione, 1-[(diiodomethyl) -sulfonyl] -4-methyl-benzene, 1-[[2- (2,4-dichlorophenyl) -1,3-dioxolane-2- Iyl] -methyl] -1H-imidazole, 1-[[2- (4-chlorophenyl) -3-phenyloxiranyl] -methyl]
-1H-1,2,4-triazole, 1- [1- [2-[(2,4-dichlorophenyl) -methoxy] -phenyl]-
Ethenyl] -1H-imidazole, 1-methyl-5-nonyl-2- (phenylmethyl) -3-pyrrolidinol, 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoro -Methyl-1,3-thiazole-5-carboxanilide, 2,2-dichloro-N- [1- (4-chlorophenyl) -ethyl] -1-ethyl-3-methyl-cyclopropanecarboxamide, 2 , 6-Dichloro-5- (methylthio) -4-pyrimidinyl-thiocyanate, 2,6-dichloro-N- (4-trifluoromethylbenzyl) -benzamide, 2,6-dichloro-N-[[4- (tri Fluoromethyl) -phenyl] -methyl] -benzamide, 2- (2,3,3-triiodo-2-propenyl) -2H-tetrazole, 2-[(1 -Methylethyl) -sulfonyl] -5- (trichloromethyl) -1,
3,4-thiadiazole, 2-[[6-deoxy-4-O- (4-O-methyl-β-D-glycopyranosyl) -α-D-glucopyranosyl] -amino] -4-methoxy-1H-pyrrolo [ Two
, 3-d] Pyrimidine-5-carbonitrile, 2-aminobutane, 2-bromo-2- (bromomethyl) -pentanedinitrile, 2-chloro-N- (2,3-dihydro-1,1,3-trimethyl -1H-inden-4-yl) -3-pyridinecarboxamide, 2-chloro-N- (2,6-dimethylphenyl) -N- (isothiocyanatomethyl) -acetamide, 2-phenylphenol (OPP). , 3,4-Dichloro-1- [4- (difluoromethoxy) -phenyl] -1H-pyrrole-2,5-dione, 3,5-dichloro-N- [cyano-[(1-methyl-2-propynyl ) -Oxy] -methyl] -benzamide, 3- (1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile, 3- [2- (4-chlorophenyl) ) -5- ethoxy-3-isoxazolidinyl] - pyridine, 4-chloro-2-cyano -N, N-dimethyl-5- (4-methylphenyl) -1
H-imidazol-1-sulfonamide, 4-methyl-tetrazolo [1,5-a] quinazolin-5 (4H) -one, 8- (1,1-dimethylethyl) -N-ethyl-N-propyl-1. , 4-Dioxaspiro [4.5] decane-2-methanamine, 8-hydroxyquinoline sulphate, 9H-xanthene-2-[(phenylamino) -carbonyl] -9-carboxylic hydrazide, bis- (1-methylethyl) -3-Methyl-4-[(3-methylbenzoyl)-
Oxy] -2,5-thiophene dicarboxylate, cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazole-
1-yl) -cycloheptanol, cis-4- [3- [4- (1,1-dimethylpropyl) -phenyl-2-methylpropyl] -2,6-dimethyl-morpholine hydrochloride, ethyl [(4 -Chlorophenyl) -azo] -cyanoacetate, potassium bicarbonate, methanetetrathiol sodium salt, methyl 1- (2,3-dihydro-2,2-dimethyl-1H-inden-1-yl) -1H-imidazole-5 -Carboxylate, methyl N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) -1-methyl-cyclohexanecarboxamide, N- ( , 6-dimethylphenyl) -2-methoxy -N- (tetrahydro-2-
Oxo-3-furanyl) -acetamide, N- (2,6-dimethylphenyl) -2-methoxy-N- (tetrahydro-2-
Oxo-3-thienyl) -acetamide, N- (2-chloro-4-nitrophenyl) -4-methyl-3-nitro-benzenesulfonamide, N- (4-cyclohexylphenyl) -1,4,5,6 -Tetrahydro-2-pyrimidineamine, N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidineamine, N- (5-chloro-2-methylphenyl) -2-methoxy-N -(2-oxo-
3-oxazolidinyl) -acetamide, N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide, N- [2,2,2-trichloro-1-[(chloroacetyl) -amino] -ethyl]- Benzamide, N- [3-chloro-4,5-bis (2-propynyloxy) -phenyl] -N '
-Methoxy-methanimidamide, N-formyl-N-hydroxy-DL-alanine-sodium salt, O, O-diethyl [2- (dipropylamino) -2-oxoethyl] -ethylphosphoramide thioate, O- Methyl S-phenylphenylpropylphosphoramide thioate, S-methyl 1,2,3-benzothiadiazole-7-carbothioate, spiro [2H] -1-benzopyran-2,1 ′ (3′H) -iso Benzofuran]
-3'-on. Bactericidal agents: bronopol, dichlorophen
), Nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octilinone
ne), furancarboxylic acid (furancarboxylic acid), oxytetracycline, probenazole (p)
robenazole), streptomycin,
Tecloftalam, copper sulfate and other copper formulations. Insecticides / Acaricides / Nematicides: Abamectin, acephate, acetamiprid, acrinathrin
rin), alanicarb, aldicarb
rb), aldoxycarb, alpha cypermethrin, alpha methrin.
thrin, amitraz, abamectin (avermec)
tin), AZ 60541, azadirachtin,
Azamethiphos, Azinphos A (azinpho)
s A), azinphos M (azophos M), azocyclotin (azo)
Cyclotin), Bacillus popilliae, Bacillus
Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, bacrovirces (bac)
uloviruses, Bear Uberia bassiana (Beauveria b)
assiana), Bearoveria tenell (Beauveria tenell)
a), bendiocarb, benfulacarb
racarb), benzultap, benzoximate (b
Enzoximate, betacyfluthrin (betacyfluthri)
n), bifenazate, bifensrin
thrin), bioethanomethrin, biopermethrin, BPMC, bromophos A
(Bromophos A), bufencarb, buprofezin, butathiophos
, Butocarboxim, butylpyridaben (bu
tylpyridaben), cadusafos, carbaryl, carbofuran, carbophenothion.
option), carbosulfan, cartapu (c)
artap), chloethocarb, chlorethoxyphos, chlorfenapyr (chlorfen)
apyr), chlorfenvinphos, chlorfluazuron, chlormephos (chlor)
mephos), chlorpyrifos, chlorpyrifos M, chlorovaporthrin (chlovap)
orthrin), cis-resmethrin, cispermethrin, crocythrin (clocyt)
hrin), cloetocarb, clofentedine
(Cloventezine), Cyanophos, Cycloprene, Cycloprothrin
n), cyfluthrin, cyhalothrin
hrin), cyhexatin (cyhexatin), cypermethrin (cype)
rmethrin), cyromazine, deltamethrin, demeton M (demethon)
M), demeton S (demeton S), demeton-S-methyl (dem)
Eton-S-methyl), diafenturon (diafenthiu)
ron), diazinon (diazinon), dichlorvos (dichlor)
vos), diflubenzuron, dimethoate
(Dimethoate), dimethylvinphos (dimethylvinpho)
s), diofenolan, disulfoton
oton), docusato-sodium, dofenapyn, efflusilanate, emamectin.
tin), empenthrin, endosulfan (en)
dosulfan), Entomophftora spp.
), Esfenvalerate, ethiofencarb, ethion, etoprophos (
ethoprophos), etofenprox,
Etoxazole, etrimfos,
Fenamiphos, fenazaquin
), Fenbutatin oxide, fenitrothion, phenothicarb (fenothi)
ocarb), fenoxacrim, phenoxycarb, fenpropathrin
), Fenpyrad, Fenpyrit
hrin), fenpyroximate (fenpyroximate), fenvalerate (fenvalerate), fipronil (Fipronil), fluazinam (fluazinam), fluazuron (fluazuron), full Bro cis Li sulphonate (flubrocythrinate), flucycloxuron (flucycloxuron), flucythrinate (Flucythrin
ate), flufenoxuron, flutenzine, fluvalinate, phonophos, fosmethilan, fosthiazate, fubufenprox (fubfenp).
rox), furatiothiocarb (granulosis viruses), halofenozide (Halofenozide), HCH, heptenofos (hep)
tenofos), hexaflumuron, hexithiazox, hydropren
e), imidacloprid, isazofos (isazofo)
s), isofenphos, isoxathion (isoxa)
thion), ivermectin, lamvda-cyhalothrin, lufenuron, malathion, mecarbam, metaldehydome, metadehyde, metadehyde.
s), Methalhizinium anis
opliae), mesalhidium flavoviride (Metharhizium)
flavoviride), methidathion, methiocarb, methomyl, methoxyphenozide, metolcarb.
arb), methoxadiazone, mevinphos (m)
evinphos), milbemectin, monocrotophos, naled, nitenpyram, nithiazine
(Nithiazine), novaluron, nuclear polyhedrosis virses, omethoate, oxamyl, oxydemethone moses humorocesomyces, paesiromyces, paesiromyces.
oseus), parathion A (parathion A), parathion M
(Parathion M), permethrin, phensoate, phorate, phosalone, phosmet, phosphamidone (ph).
osphamidon), phoxim, pirimicarb (piri)
micarb), pirimiphos A, pirimiphos
M (pirimiphos M), profenofos
, Promecarb, propoxur,
Prothiophos, prosoate
), Pymetrozine, pyraclofos (pyraclo)
fos), pyrethmethrin, pyrethrum (pyr)
Ethrum), pyridaben, pyridathion (pyri)
dathion), pyrimidifen, pyriproxyphen, quinalphos, ribavirin, salithion, salifion, sebufos, serafofen, silafulos, silafluofen, sebufos, silafluofen Sulprofos, tau-fluvalinate, tebufenozide
(Tebufenozide), tebufenpyrad (tebufenpyrad)
), Tebupirimiphos, teflubenzuron (t
eflubenzuron, tefluthrin, temephos, temivinphos, terbufos, tetrachlorvinpho (tetrachlorvi)
nphos), theta-cypermethrin (theta-cypermethrin)
), Thiamethoxam, thiapronil (thiap)
ronil), thiatriphos, thiocyclam hydrogen oxalate (thiocyclam hydrogen oxa)
late), thiodicarb, thiophanox (th)
iofanox), thuringiensin, tralocythrin, tralomethrin
rin), triarathene, triazamate (tri)
azamate), triazophos, triazuron (t
riazuron), triclophenidine
), Trichlorfon, triflumuron
umuron), trimesacarb (trimethacarb), vamidotion (vanimithion), vaniliprol (vanilipr)
ole), Verticillium lecanni (Verticillium lecan)
ii), YI 5302, zeta-cypermethrin, zolaprofos, (1R-cis)-[5- (phenylmethyl) -3-furanyl] -methyl-3-
[(Dihydro-2-oxo-3 (2H) -furanilidene) -methyl] -2,2-
Dimethylcyclopropanecarboxylate, (3-phenoxyphenyl) -methyl-2,2,3,3-tetramethylcyclopropanecarboxylate, 1-[(2-chloro-5-thiazolyl) methyl] tetrahydro-3,5- Dimethyl-N-nitro-1,3,5-triazine-2 (1H) -imine, 2- (2-chloro-6-fluorophenyl) -4- [4- (1,1-dimethylethyl) phenyl]- 4,5-dihydro-oxazole, 2- (acetyloxy) -3-docesyl-1,4-naphthalenedione, 2-chloro-N-[[[4- (1-phenylethoxy) -phenyl] -amino]
-Carbonyl] -benzamide, 2-chloro-N-[[[4- (2,2-dichloro-1,1-difluoroethoxy) -phenyl] -amino] -carbonyl] -benzamide, 3-methylphenylpropylcarbamate, 4- [4- (4-ethoxyphenyl) -4-methylpentyl] -1-fluoro-
2-phenoxy-benzene, 4-chloro-2- (1,1-dimethylethyl) -5-[[2- (2,6-dimethyl-4-phenoxyphenoxy) ethyl] thio] -3 (2H) -pyridazinone , 4-chloro-2- (2-chloro-2-methylpropyl) -5-[(6-iodo-
3-pyridinyl) methoxy] -3 (2H) -pyridazinone, 4-chloro-5-[(6-chloro-3-pyridinyl) methoxy] -2- (3,4
-Dichlorophenyl) -3 (2H) -pyridazinone, Bacillus thuringiensis strain EG-2348 (Bacillus tho)
ringingensis strain EG-2348), 2-benzoyl-1- (1,1-dimethylethyl) -hydrazinobenzoic acid, 2,2-dimethyl-3- (2,4-dichlorophenyl) -2-oxo-1-oxaspiro [ 4.5] Dec-3-en-4-ylbutanoate, [3-[(6-chloro-3-pyridinyl) methyl] -2-thiazolidinylidene]
-Cyanamide, dihydro-2- (nitromethylene) -2H-1,3-thiazine-3 (4H) -carboxaldehyde, ethyl [2-[[1,6-dihydro-6-oxo-1- (phenylmethyl ) -4
-Pyridazinyl] oxy] ethyl] -carbamate, N- (3,4,4-trifluoro-1-oxo-3-butenyl) -glycine, N- (4-chlorophenyl) -3- [4- (difluoromethoxy) Phenyl]-
4,5-Dihydro-4-phenyl-1H-pyrazole-1-carboxamide, N-[(2-chloro-5-thiazolyl) methyl] -N'-methyl-N "-nitro-guanidine, N- Methyl-N '-(1-methyl-2-propenyl) -1,2-hydrazine dicarbothioamide, N-methyl-N'-2-propenyl-1,2-hydrazine dicarbothioamide, O, O-diethyl [ 2- (dipropylamino) -2-oxoethyl] -ethylphosphoramidothioate.

It is also possible to combine other known active compounds, such as herbicides, or fertilizers and growth regulators.

Furthermore, the compounds of formula (I) according to the invention also have a very good antifungal activity (anti).
(mycotic actions) are shown. The compounds are especially suitable for the treatment of Dermatophytes and yeasts, fungi and diphasic fungi (dip).
basic fungi [eg Candida albicans (Candida
albicans), Candida glabra
Candida species such as ta)], Epidermophyton floccosum
Aspergillus fumigatus such as Epidermophyton species, Aspergillus niger and Aspergillus fumigatus
rgillus species), Trichophyton
Trichophytons species such as Mentagrophytes
, S. canis and Audoan microspores (Microsporo)
n canis and audouiniii) and the like (Micros
It exhibits a very broad spectrum antifungal activity against poron species). The list of these microorganisms is by no means descriptive of the limits of the fungal spectrum which can be controlled, but of descriptive nature.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions.
ns), suspensions, wettable powders, pastes, soluble powders, powders and granules. Application is in the customary manner, for example by means of watering, atomizing, spraying, spreading.
), Dusting (dusting), foaming, coating and the like. Furthermore, the active compounds can be applied by the ultra-low-volume method or the active compound preparations or the active compounds themselves can be injected into the soil. It is also possible to treat the seeds of the plants.

When the active compounds of the invention are used as fungicides, the application rates can be varied within a relatively wide range, depending on the type of application. When treating parts of plants, the application rates of active compound are usually from 0.1 to 10,000 g / ha, preferably from 10 to 1000 g / ha. When processing seeds,
The application rate of the active compound is usually 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g per kilogram of seed. When treating the soil, the application rates of the active compound are usually from 0.1 to 10,000 g / ha, preferably from 1 to 5000 g / ha.

Preparation Examples Example 1: 2-{[3- (formylamino) -2-hydroxybenzoyl] amino} -3
Ethyl-(4-hydroxyphenyl) propanoate Method b) 2.0 g (5.1 mmol) of ethyl 2-[(2-hydroxy-3-nitrobenzoyl) amino] -3- (4-hydroxyphenyl) propanoate was added. 60 ml formic acid
Suspended therein, 2.0 g of Raney nickel was mixed. The mixture was stirred at 90 ° C. for 1 hour and then filtered. The filtrate was concentrated, taken up in dichloromethane and washed with distilled water. The organic phase was dried over sodium sulphate and then concentrated to dryness. Purification was carried out on silica gel with an eluent mixture (6: 1 ratio of ethyl acetate / cyclohexane). 1.34 g (70% of theory) of ethyl 2-{[3- (formylamino) -2-hydroxybenzoyl] amino} -3- (4-hydroxyphenyl) propanoate are thus obtained. HPLC: logP = 1.83 The compounds of general formula (Ia) listed in Table 1 below are obtained analogously to Example 1 and according to the general description of the process according to the invention:

[0114]

[Chemical 34]

[0115]

[Table 1]

[0116]

[Table 2]

[0117]

[Table 3]

[0118]

[Table 4]

[0119]

[Table 5]

[0120]   * Represents the bonding position to the nitrogen atom.

The value of logP is calculated by EEC Directive 79/831 Annex.
V. Determined by HPLC (high performance liquid chromatography) according to A8 (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).

Preparation of Intermediates of Formula (Ib) Example (IV-1) Ethyl 2-[(2-hydroxy-3-nitrobenzoyl) amino] -3- (4-hydroxyphenyl) propanoate Method d) D , L-tyrosine ethyl ester hydrochloride 1.78 g (8.0 mmol) are dissolved in 20 ml of tetrahydrofuran and mixed with 1.1 ml (8 mmol) of triethylamine. At 0 ° C., 3-nitrosalicylic acid chloride (8.0 mmol) dissolved in 25 ml of tetrahydrofuran is added dropwise to the reaction mixture with stirring. Allow the reaction mixture to warm to room temperature over 16 hours. The precipitated triethylammonium chloride is filtered off and the remaining solution is concentrated using a rotary evaporator. The residue is taken up in 200 ml of ethyl acetate and the mixture is extracted with 200 ml of distilled water. Then the organic phase is dried over sodium sulphate. The solvent is removed using a rotary evaporator. Eluent mixture (10: 1 ratio of ethyl acetate / cyclohexane)
Purify on silica gel using.

Thus, 2-[(2-hydroxy-3-nitrobenzoyl) amino]
2.14 g of ethyl 3- (4-hydroxyphenyl) propanoate (theoretical value of 69
%) Is obtained. HPLC: logP = 2.28 The compounds of general formula (IV) listed in Table 2 below are obtained analogously to example (IV-1) and according to the general description of the process according to the invention:

[0124]

[Chemical 35]

[0125]

[Table 6]

[0126]

[Table 7]

[0127]

[Table 8]

[0128]

[Table 9]

[0129]

[Table 10]

[0130]   * Represents the bonding position of the nitrogen atom.

The logP value is the EEC Directive 79/831 Annex V.
． Determined by HPLC (high performance liquid chromatography) according to A8 (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).

Use Examples: Example A Phytophthora Test (Tomato) / Protection Solvent: Acetone 24.5 parts by weight Dimethylacetamide 24.5 parts by weight Emulsifier: Alkylaryl polyglycol ether 1.0 parts by weight Active compound 1 part by weight of the active compound is mixed with the abovementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the given concentration.

To test for protective activity, young plantlets are sprayed with the active compound preparation at the stated application rate. After the spray coating has dried, Phytophthora infest
seedlings are inoculated with an aqueous spore suspension of ans). Then, at about 20 ° C, relative atmospheric humidity 1
Place seedlings in a 00% culture hut.

Evaluation is carried out 3 days after the inoculation. 0% means an efficacy corresponding to that of the control, whereas an efficacy of 100% means that no infection is observed.

In this test, the substances according to the invention described for Examples (2), (4), (8) and (12) exert an efficacy of 92% or higher at an application rate of 100 g / hectare.

Example B Plasmopara Test (Vines) / Protection Solvent: Acetone 24.5 parts by weight Dimethylacetamide 24.5 parts by weight Emulsifier: Alkylaryl polyglycol ether 1.0 parts by weight Suitable active compounds To prepare such formulations, 1 part by weight of active compound is mixed with the abovementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the given concentration.

To test for protective activity, young plants are sprayed with the active compound formulation at the stated application rate. After the spray coating has dried, the seedlings are subjected to downy mildew (Plasmopara v).
Iticola) is inoculated with an aqueous suspension of spores and then placed in a culture chamber at approximately 20 ° C. and 100% relative atmospheric humidity for 1 day. The seedlings are then placed in a greenhouse at approximately 21 ° C. and atmospheric humidity of approximately 90% for 5 days. The seedlings are then moistened and placed in a culture hut for 1 day.

Evaluation is carried out 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

In this test, the substances of the present invention described in Examples (2), (4), (6), (8) and (12) exert an efficacy of 97% or more at an application rate of 100 g / ha. To do.

Example C Botrytis test (legumes) / protection Solvent: Acetone 24.5 parts Dimethylacetamide 24.5 parts Emulsifier: Alkylaryl polyglycol ether 1.0 parts Appropriate formulation of active compound. 1 part by weight of the active compound is mixed with the abovementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the given concentration.

To test for protective activity, young plantlets are sprayed with the active compound formulation at the stated application rate. After the spray coating has dried, Botrytis cinerea
) Place 2 small pieces of agar covered with) on each leaf. 20 seedlings were inoculated
Place in a dark room at 100 ° C and 100% relative atmospheric humidity.

Two days after inoculation, the size of the infected area on the leaves is evaluated. 0% means an efficacy corresponding to that of the control, whereas an efficacy of 100% means that no infection is observed.

In this test, the substances according to the invention described in Examples (2), (4), (6), (8) and (12) exert an efficacy of 90% or more at an application rate of 500 g / hectare. To do.

Example D Pyricularia Test (Rice) / Protection Solvent: Acetone 48.8 parts by weight Emulsifier: Alkylaryl polyglycol ether 1.2 parts by weight Active to prepare suitable formulations of active compound. 1 part by weight of the compound is mixed with the abovementioned amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test for protective activity, young rice seedlings are sprayed with the active compound formulation at the specified application rate. After the spray coating has dried, the rice blast fungus (Pyriculari)
a oryzae) is inoculated with an aqueous spore suspension and then left at 100% relative atmospheric humidity and 26 ° C. for 24 hours. The seedlings are then placed in a greenhouse with a relative atmospheric humidity of 80% and a temperature of 26 ° C.

Evaluation is carried out 7 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.

In this test, Examples (1), (8), (9), (10) and (12)
The substance of the present invention described above exhibits an efficacy of 89% or more at an application rate of 750 g / ha.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C07C 233/87 C07C 233/87 237/32 237/32 237/36 237/36 237/52 237/52 323 / 59 323/59 C07D 207/26 C07D 207/26 209/20 209/20 // C07B 61/00 300 C07B 61/00 300 (81) Designated country EP (AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LU, MC, NL, PT, SE), OA (BF, BJ, CF, CG, CI, CM, GA, GN, GW, ML, MR, NE, SN, TD, TG), AP (GH, GM, KE, LS, MW, MZ, SD, SL, SZ, TZ, UG, ZW), EA (AM, AZ, BY, KG, KZ, MD) , RU, TJ, T ), AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BY, BZ, CA, CH, CN, CR, CU, CZ, DE, DK, DM, DZ, EE , ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NO, NZ, PL, PT, RO, RU, SD, SE, SG, SI, SK, SL, TJ, TM, TR , TT, TZ, UA, UG, US, UZ, VN, YU, ZA, ZW (72) Inventor Gaier, Herbert Deutsche Day-40789 Monheim Zandshuttrase 66 (72) Inventor, Jordan, Siuteh Juan Deutsche Day 51061 Cologne-Morgeng Raven 14 (7 2) Inventor Baupel, Martein Germany Day 42799 Reichlingen Lantrad-Trimborn-Schutlerse 47 (72) Inventor Bahendorf-Neumann, Ulrike German Day-56566 Neubeat Obera Markenbeek 85 (72) Inventor Kuku, Karl - Heinz Germany Day -40,764 Langenfeld felt, Pastor - Leh - Shiyutorase 30 ah F-term (reference) 4C069 AB15 BB02 BB38 4C204 BB02 BB04 CB03 DB19 EB01 FB01 GB01 4H006 AA01 AA02 AA03 AB03 AC53 BA21 BB17 BJ20 BJ50 BM30 BM72 BN10 BN30 BP30 BP60 BT12 BT14 BT22 BT32 BU26 BV36 BV53 BV54 TA04 TB52 4H011 AA01 BA01 BB06 BC03 BC05 DA16 DC05 DD03 DE15 4H039 CA71 CB90

Claims (15)

[Claims] 1. Formula (I) for controlling organisms that cause damage to plants and industrial materials. {Wherein R ¹ represents hydrogen or alkyl, R ² represents hydrogen or alkyl, or R ³ represents a group [Wherein A is oxygen, sulfur or-(N-R ⁹ )-(wherein R ⁹ represents hydrogen or alkyl, or, together with R ⁶ and the nitrogen atom to which they are attached, Form an optionally substituted heterocyclic ring), R ⁴ represents hydrogen, optionally substituted alkyl or optionally substituted aryl, or R ² and R ⁴ are Together with the atom to which they are attached form a heterocyclic ring, R ⁵ represents hydrogen or alkyl, or R ⁴ and R ⁵ together with the carbon atom to which they are attached. To form a carbocyclic ring, R ⁶ represents hydrogen or in each case optionally substituted alkyl,
Represents cycloalkyl, aryl or heterocyclyl, R ⁷ represents hydrogen or alkyl, R ⁸ represents hydrogen or alkyl and Z represents hydrogen or in each case optionally substituted alkyl, alkylcarbonyl Represents cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl.
] Is represented. } Use of a compound of. 2. R¹ Represents hydrogen or methyl, R² Is hydrogen or C₁ -C_Four Represents alkyl, and R³ Is the base [Chemical 3] [In the group, A is oxygen, sulfur or-(N-R⁹ )-(Where R⁹ Is also hydrogen
Preferably represents alkyl having 1 to 4 carbon atoms, or R⁶ And those
Has 3 to 7 ring members together with the nitrogen atom to which C is attached, C ₁  -C_Four Form a heterocyclic ring optionally substituted with alkyl. ), R^Four Is hydrogen, or in each case 1 to 6 carbon atoms in the alkyl moiety.
Having alkoxy, alkylthio, alkoxycarbonyl or alkylcarl
Represents an alkyl, optionally substituted with bonyloxy, or an aryl moiety
Arylcarbonyl, where is optionally substituted with hydroxyl, formyloxy
Represents an alkyl optionally substituted with luoxy, or in each case
Having 1 to 6 carbon atoms in the alkyl moiety and in each case an aryl
Aryl or heterothel, optionally substituted on the aryl or heterocyclyl moiety.
Represents cyclyl, arylalkyl or heterocyclylalkyl, or
R² And R^Four Is 3 to 6 ring structures together with the atoms to which they are attached.
Forming a heterocyclic ring having components R^Five Is hydrogen or C₁ -C_Four Represents alkyl, or R^Four And R^Five Together with the carbon atom to which they are attached, has 3 to 6
Forming a carbocyclic ring having ring members, R⁶ Is hydrogen or C₁ -C₁₂Alkyl; C₁ -C_Four Optionally with alkyl
Converted C₃ -C₇ Represents cycloalkyl or aryl; 1 in the alkyl moiety
Arylalkyl having from 6 to 6 carbon atoms; heterocyclyl; or
Represents a heterocyclylalkyl having 1 to 6 carbon atoms in the rualkyl moiety,
Each of these may optionally contain an aryl or heterocyclyl moiety.
Have been replaced, R⁷ Is hydrogen or C₁ -C_Four Represents alkyl, R⁸ Is hydrogen or C₁ -C_Four Represents alkyl, and Z is hydrogen or C₁ -C₁₂Alkyl or alkylcarbonyl; C₁ -C _Four  C optionally substituted with alkyl₃ -C₇ Cycloalkyl or cycloa
Represents alkyl, aryl, arylcarbonyl; one in the alkyl part
Arylalkyl having from 6 to 6 carbon atoms, arylalkylcarbonyl;
Heterocyclyl, heterocyclylcarbonyl; 1 to 6 carbons in the alkyl moiety
Heterocyclylalkyl or heterocyclylalkylcarbo having an elementary atom
And each of these is an aryl moiety or heterocyclyl.
The parts are optionally replaced. ] Plant and industry of the compound of formula (I) according to claim 1, characterized in that
Use to control organisms that cause damage to materials. 3. R ¹ represents hydrogen or methyl, R ² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and R ³ is , Group [Wherein A is oxygen, sulfur or-(N-R ⁹ )-(wherein R ⁹ is hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t −
Butyl, or together with R ⁶ and the nitrogen atom to which they are attached,
Represents pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl or hexahydroazepinyl, optionally substituted with methyl or ethyl. ),
R ⁴ represents hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, optionally substituted with hydroxyl, formyloxy, phenyl moieties, Represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted with propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy, or a phenyl moiety or heterocyclyl phenyl moiety is optionally substituted in each case, benzyl, 1-phenethyl, or represents 2-phenethyl or indolylmethyl, or R ² and R ^4, together with the atoms to which they are attached Roridin represents ring or piperidine ring, R ⁵ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, or represents s- or t- butyl, or R ⁴ and R ^5, they Represents a cyclopropane ring, a cyclopentane or a cyclohexane ring together with the bonded carbon atom, R ⁶ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s-
Or t-butyl, pentyl, hexyl, heptyl, octyl; represents cyclopentyl or cyclohexyl optionally substituted with methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or Phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl or moles, where the phenyl or heterocyclyl moiety is optionally substituted in each case Represents folinylbutyl or represents pyrrolidonyl-substituted methyl, ethyl or propyl, R ⁷ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. represents, R ⁸ is Represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and Z is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-. , S- or t-butyl, pentyl, hexyl, heptyl, octyl, methylcarbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s.
-Or t-butylcarbonyl, pentylcarbonyl, hexylcarbonyl,
Heptylcarbonyl, octylcarbonyl; methyl, ethyl, n- or i-
Phenyl, cyclohexyl, cyclohexyl, cyclopentylcarbonyl or cyclohexylcarbonyl optionally substituted with propyl, n-, i-, s- or t-butyl, wherein phenyl or heterocyclyl moieties are in each case optionally substituted phenyl, Benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl, morpholinylbutyl, phenylcarbonyl, benzylcarbonyl, 1-phenethylcarbonyl,
2-phenethylcarbonyl, phenylcarbonylpropylcarbonyl, phenylcarbonylbutylcarbonyl, phenylcarbonylpentylcarbonyl or phenylcarbonylhexylcarbonyl, pyrrolidinylcarbonyl, morpholinylcarbonyl, pyrrolidinylcarbonylbutylcarbonyl or morpholinylcarbonylbutylcarbonyl . ] Use of a compound of formula (I) according to claim 1 for controlling organisms which cause damage to plant and industrial materials. 4. Formula (Ia): {Wherein R ¹¹ represents hydrogen or alkyl, R ¹² represents hydrogen or alkyl, or R ¹³ represents a group [Wherein A is oxygen, sulfur or-(N-R ¹⁹ )-(wherein R ¹⁹ represents hydrogen or alkyl, or, together with R ¹⁶ and the nitrogen atom to which they are attached, Form an optionally substituted heterocyclic ring), R ¹⁴ represents hydrogen, optionally substituted alkyl or optionally substituted aryl, or R ¹² and R ¹⁴ are Together with the atom to which it is attached form a heterocyclic ring, R ¹⁵ represents hydrogen or alkyl, or R ¹⁴ and R ¹⁵ are together with the carbon atom to which they are attached a carbon atom. Form a cyclic ring, R ¹⁶ represents hydrogen or in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl, R ¹⁷ represents hydrogen or alkyl and R ¹⁸ is hydrogen If Represents alkyl, Z ¹ represents hydrogen or optionally substituted alkyl, alkylcarbonyl, cycloalkyl, cycloalkylcarbonyl, aryl, arylcarbonyl, heterocyclyl or heterocyclylcarbonyl, R ²⁰ represents hydrogen, Optionally substituted alkyl or optionally substituted aryl or hetaryl, or R ¹² and R ²⁰ together with the atom to which they are attached form a heterocyclic ring, R ²¹ is Representing hydrogen or alkyl, or R ²⁰ and R ^{21 taken} together with the carbon atom to which they are attached form a carbocyclic ring. ] Is represented. } The compound of. 5. R ¹¹ represents hydrogen or methyl, R ¹² represents hydrogen or C ₁ -C ₄ alkyl and R ¹³ is a radical of the formula [Wherein A is oxygen, sulfur or-(N-R ¹⁹ )-(wherein R ¹⁹ represents hydrogen or alkyl having 1 to 4 carbon atoms, or R ¹⁶ and those C _1- having 3 to 7 ring members together with the nitrogen attached thereto
Form a heterocyclic ring optionally substituted with C ₄ alkyl. R ¹⁴ represents hydrogen or is an alkyl optionally substituted with an alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy having in each case 1 to 6 carbon atoms in the alkyl moiety. Represents, or represents an alkyl optionally substituted with arylcarbonyloxy, where the aryl moiety is optionally substituted with hydroxyl, formyloxy, or in each case has 1 to 6 carbon atoms in the alkyl moiety. And having in each case an aryl or heterocyclyl moiety represents an optionally substituted aryl, heterocyclyl, arylalkyl or heterocyclylalkyl, or R ¹² and R ¹⁴ together with the atom to which they are attached Become 3 to 6 rings Form a heterocyclic ring having the constituents, R ¹⁵ represents hydrogen or C ₁ -C ₄ alkyl, or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached have from 3 to 3 Forming a carbocyclic ring having 6 ring members, R ¹⁶ represents hydrogen or C ₁ -C ₁₂ alkyl; C ₃ -C ₇ cycloalkyl optionally substituted with C ₁ -C ₁₄ alkyl , Aryl; arylalkyl having 1 to 6 carbon atoms in the alkyl moiety; heterocyclyl; 1 in the alkyl moiety
Represents a heterocyclylalkyl having from 1 to 6 carbon atoms, each of which is optionally substituted with an aryl or heterocyclyl moiety, or represents a C ₁ -C ₄ alkyl substituted with pyrrolidonyl, R ¹⁷ represents hydrogen or C ₁ -C ₄ alkyl, and R ¹⁸ represents hydrogen or C ₁ -C ₄ alkyl, Z ¹ represents hydrogen or C ₁ -C ₁₂ alkyl or alkylcarbonyl; C _1-
Represents C ₃ -C ₇ cycloalkyl or cycloalkylcarbonyl optionally substituted with C ₄ alkyl, aryl, arylcarbonyl; 1 in the alkyl moiety
Arylalkyl having from 1 to 6 carbon atoms, arylalkylcarbonyl; heterocyclyl, heterocyclylcarbonyl; representing heterocyclylalkyl or heterocyclylalkylcarbonyl having from 1 to 6 carbon atoms in the alkyl moiety, and each of these being aryl A moiety or a heterocyclyl moiety is optionally substituted, R ²⁰ is hydrogen; or formyloxy, arylcarbonyloxy optionally substituted with an aryl moiety, or in each case 1 to 6 carbon atoms in the alkyl moiety. 2 to 6 in the alkyl moiety; alkoxy, alkylthio, or represents C ₁ -C ₄ alkyl optionally substituted by alkoxycarbonyl or alkylcarbonyloxy or aryl, heterocyclyl having Or substituted with an arylalkyl having 1 to 6 carbon atoms or a heterocyclylalkyl having 1 to 6 carbon atoms in each of the alkyl moieties, each of which is optionally substituted with an aryl or heterocyclyl moiety. Benzyl or R ¹² and R ²⁰ together with the atom to which they are attached form a heterocyclic ring having 3 to 6 ring members, R ²¹ is hydrogen or C Representing _1- C ₄ alkyl, or R ²⁰ and R ²¹ together with the carbon atom to which they are attached form a carbocyclic ring having 3 to 6 ring members. ] The compound of formula (Ia) according to claim 4, characterized in that 6. R ¹¹ represents hydrogen or methyl, R ¹² represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, and R ¹³ is a radical. [Chemical 8] [Wherein A is oxygen, sulfur or-(N-R ¹⁹ )-(wherein R ¹⁹ is hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-). Butyl, or pyrrolidinyl, morpholinyl, piperidinyl, piperazinyl or hexahydroazepinyl, optionally substituted with methyl or ethyl together with R ¹⁶ and the nitrogen atom to which they are attached). R ¹⁴ represents hydrogen or phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, optionally substituted with hydroxyl, formyloxy, phenyl moieties, Propylcarbonyloxy, pentylcarbonyloxy or Methyl optionally substituted with sills carbonyloxy,
Phenyl, benzyl, 1-phenethyl, representing ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or optionally substituted with a phenyl or heterocyclyl moiety, 2 -Phenethyl or indolylmethyl, or R ¹² and R ¹⁴ together with the atom to which they are attached represent a pyrrolidine ring or piperidine ring, R ¹⁵ is hydrogen, methyl, ethyl, n- or represents i-propyl, n-, i-, s- or t-butyl, or R ¹⁴ and R ¹⁵ together with the carbon atom to which they are attached are cyclopropane ring, cyclopentane or cyclohexane. represents a ring, R ¹⁶ is hydrogen, methyl, ethyl, n- or i- propyl, n-, i-, s- or t- butyl, pentyl Hexyl, heptyl, octyl; methyl, ethyl, n- or i- propyl, n-, i-, s- or t- butyl optionally or represents cyclopentyl or cyclohexyl substituted by, or phenyl,
Benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl or morpholinylbutyl, each of which is substituted on the phenyl or heterocyclyl moiety. , Or
Or methyl, ethyl or propyl substituted with pyrrolidonyl, R ¹⁷ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s-
Or represents a t- butyl, and R ¹⁸ is hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, represent s- or t- butyl, Z ¹ is hydrogen, methyl, ethyl, n- Or i-propyl, n-, i-, s- or t-butyl, pentyl, hexyl, heptyl, octyl, methylcarbonyl, ethylcarbonyl, n- or i-propylcarbonyl, n-, i-, s
-Or t-butylcarbonyl, benzylcarbonyl, hexylcarbonyl,
Heptylcarbonyl, octylcarbonyl; methyl, ethyl, n- or i-
Represents cyclopentyl, cyclohexyl, cyclopentylcarbonyl or cyclohexylcarbonyl optionally substituted with propyl, n-, i-, s- or t-butyl, phenyl, benzyl, 1-phenethyl, 2-phenethyl, phenylpropyl, phenylbutyl, Phenylpentyl or phenylhexyl, pyrrolidinyl, morpholinyl, pyrrolidinylbutyl, morpholinylbutyl, phenylcarbonyl, benzylcarbonyl, 1-phenethylcarbonyl, 2-phenethylcarbonyl, phenylcarbonylpropylcarbonyl, phenylcarbonylbutylcarbonyl, phenylcarbonylpentylcarbonyl Or phenylcarbonylhexylcarbonyl, pyrrolidinylcarbonyl, morpholinylcarbonyl, pyrrolidinyl Represents Rubo sulfonyl butylcarbonyl or morpholinylcarbonyl butylcarbonyl, and, each of which are optionally substituted phenyl moiety or heterocyclyl moiety, R ²⁰ is substituted or represents hydrogen, or formyl, phenyl moiety is optionally Methyl, ethyl, n-, optionally substituted with phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy, propylcarbonyloxy, phenylcarbonyloxy or hexylcarbonyloxy. Or i
Represents -propyl, n-, i-, s- or t-butyl or phenyl, 1
-Phenethyl, 2-phenethyl or indolylmethyl, each of which is optionally substituted on the phenyl or heterocyclyl moieties, or substituted benzyl, or R ¹² and R ²⁰ are R ²¹ together with the atom to which they are attached represents a pyrrolidine ring or a piperidine ring, R ²¹ represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. Or R ²⁰ and R ²¹ together with the carbon atom to which they are attached represent a cyclopropane ring, a cyclopentane or a cyclohexane ring. ] The compound of formula (Ia) according to claim 4, characterized in that 7. Formula (II-a): Where R ¹² is as defined above and R ¹³ is a group [Wherein each of A, R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Z ¹ and R ²¹ is as defined above, R ²² is formyloxy; A substituted arylcarbonyloxy; or C ₁ -C ₄ alkyl substituted in each case by an alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy having 1 to 6 carbon atoms in the alkyl moiety, or Aryl, heterocyclyl, which represents unsubstituted C ₂ -C ₄ alkyl; arylalkyl having 2 to 6 carbon atoms in the alkyl moiety or heterocyclylalkyl having 1 to 6 carbon atoms in the alkyl moiety (each of which Represents an optionally substituted aryl or heterocyclyl moiety) or a substituted benzene. Or represents Le, or R ²² and R ^12, together with the atoms to which they are attached form a heterocyclic ring, R ²² and R ^21, together with the carbon atoms to which they are attached To form a carbocyclic ring. ] Is represented. } The compound of. 8. R ¹² is as defined above and R ¹³ is a group of the formula [Wherein each of A, R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Z ¹ and R ²¹ is as defined above, and R ²² is a formyloxy or aryl moiety. Represents a substituted arylcarbonyloxy, or C ₁ -C ₄ alkyl substituted in each case by an alkoxy, alkylthio, alkoxycarbonyl or alkylcarbonyloxy having 1 to 6 carbon atoms in the alkyl moiety, or Represents unsubstituted C ₂ -C ₄ alkyl, aryl, heterocyclyl, arylalkyl having 2 to 6 carbon atoms in the alkyl moiety or heterocyclylalkyl having 1 to 6 carbon atoms in the alkyl moiety (each of which Represents an optionally substituted aryl or heterocyclyl moiety) or a substituted benzene. Or represents Le, or R ²² and R ^12, if they represent a pyrrolidine ring or a piperidine ring together with the atoms to which they are attached or R ²² and R ^21, the carbon atom to which they are attached Represents a cyclopentane or cyclohexane ring together with. ] The compound of formula (II-a) according to claim 7, characterized in that 9. R ¹² is as defined above and R ¹³ is a group of the formula [Wherein each of A, R ¹⁴ , R ¹⁵ , R ¹⁶ , R ¹⁷ , R ¹⁸ , Z ¹ and R ²¹ is as defined above, R ²² is a formyloxy or phenyl moiety, Substituted phenylcarbonyloxy, methoxy, ethoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, methylcarbonyloxy, ethylcarbonyloxy,
Methyl, ethyl, n- or i-propyl, each substituted with propylcarbonyloxy, pentylcarbonyloxy or hexylcarbonyloxy,
represents n-, i-, s- or t-butyl or represents unsubstituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl, phenyl, 1-
Represents phenethyl, 2-phenethyl or indolylmethyl, each of which is optionally substituted in the phenyl or heterocyclyl moiety, or represents a substituted benzyl, or R ²² and R ¹² are the groups to which they are attached. Represents a pyrrolidine ring or a piperidine ring, or R ²² and R ²¹ represent a cyclopentane ring or a cyclohexane ring together with the carbon atom to which they are attached. ] The compound of formula (II-a) according to claim 7, characterized in that 10. A compound of formula (IV-a): [In the formula, each of R ¹² and R ¹³ is as defined in claim 4. ] Compound of 11. A composition comprising a bulking agent and / or carrier and, if appropriate, a surfactant, characterized in that it comprises at least one compound as defined in claims 4 to 6. Composition. 12. A compound as defined in claims 4 to 6 or claim 1.
A method for controlling pests, which comprises causing the composition defined in 1 to act on pests and / or their habitat. 13. Use of a compound as defined in claims 4 to 6 or a composition as defined in claim 11 for controlling pests. 14. A method for producing a pest control agent, which comprises mixing the compound defined in claims 4 to 6 with a filler and / or a surfactant. 15. a) General formula (II): [Wherein each of R ¹² and R ¹³ is as defined above. ] In the presence of a diluent, if appropriate in the presence of an acid acceptor, and if appropriate in the presence of another reaction aid, of the general formula (III
) [Chemical 15] Wherein R ¹¹ is as defined above and X ¹ represents halogen, hydroxyl, alkoxy or alkylcarbonyloxy. ] Or with b) the general formula (IV): [Wherein each of R ¹² and R ¹³ is as defined above. ] The nitrosalicylamides according to claim 4 are reacted with formic acid in the presence of a catalyst, if appropriate, and in the presence of another reaction aid, if appropriate. A method for producing a compound of Ia).