DE19924273A1 - New nitro- or cyano-imideamide derivatives, used as insecticides, acaricides, ectoparasiticides or especially nematocides - Google Patents

Abstract

N-(Nitro- or cyano)-imideamide derivatives (I) are new. Imideamide derivatives of formula (I) are new. R = CN or NO2; R1 = H; or alkyl, cycloalkyl or phenyl (all optionally substituted); R2 = H; or alkyl or cycloalkyl (both optionally substituted); R3 = -CR4R5-XR6, -YR7 or -OR8; R4, R5 = H; or alkyl or cycloalkyl (both optionally substituted); R6, R7 = aryl, cycloalkyl, cycloalkenyl or nitrogen-free mono-, bi- or tricyclic heterocycle (all optionally substituted); R8 = alkyl or optionally substituted aryl; X = direct bond, alkanediyl, alkenediyl or alkynediyl; or -A-O-, -A-S-, A-O-A'-, -A-S-A'-, -A-N(alkyl)- or -A-N(alkyl)-A'- (all bonded to via A to CR4R5); A, A' = alkenediyl; Y = direct bond; or -O-A-, -O-A''-O-, -O-A''-S-, -O-A''-SO-, -O-A''-SO2-, -O-A''-O-A'- or -O-A''-S-A'- (all bonded to the N of (I) via O); A'' = alkanediyl having at least 2C between the heteroatoms; provided that compounds (I; R = CN, R2 = H) are excluded where: (i) R1 = n-butyl and R3 = 2-chlorobenzyl, (ii) R1 = Me and R3 = 3-(2-chlorophenyl)-allyl, 3-(2,6-dichlorophenyl)-allyl or Ph, (iii) R1 = Et and R3 = Ph or (iv) R1 = isopropyl and R3 = p-tolyl. An Independent claim is included for the preparation process of (I).

Description

The present application relates to new imidamide derivatives, a process for their Manufacture and its use for controlling animal pests.

Certain imidamide derivatives are already known (cf. WO 91 04 965, WO 93 04 032, EP 0 403 159; J. Organomet. Chem. (1975), 97 (1), pp. 39-44; Bull. Soc. Chim. Belg. (1981), 90 (1), pp. 89-98). Also some of these have insecticidal properties Connections were known.

New imidamide derivatives of the general formula (I) have now been found

in which
R represents cyano or nitro,
R ^{1 represents} hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
R ^{2 represents} hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl and R ^{3 represents} the groupings

stands,
in which
R ⁴ and R ⁵ independently of one another represent hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl,
R ⁶ and R ⁷ independently of one another represent optionally substituted aryl, optionally substituted cycloalkyl or an optionally substituted mono- or bicyclic, nitrogen-free heterocycle,
R ^{8 represents} alkyl or optionally substituted aryl,
X for a single bond, for in each case straight-chain or branched alkanediyl, alkenediyl, alkindiyl and for the groups -AO-, -AS-, -AO-A'-, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'- is where in part A to the carbon atom of the group -C (R ⁴ R ⁵ ) -XR ^{6 is} bound;
Alk stands for alkyl and
A and A 'independently of one another represent straight-chain or branched alkanediyl and
Y for a single bond and the groupings -OA-, -O-A '' - O-, -O-A '' - S-, -O-A '' - SO-, -O-A '' - SO ₂ -, -O-A '' - O-A'- or -O-A '' - S-A'-, the O atom of this group always being linked to the N atom of the basic structure of the formula (I) is;
A and A 'have the meaning given above and
A '' stands for straight-chain or branched alkanediyl with at least 2 carbon atoms between the heteroatoms.

with the proviso that for R = CN and R ² = H the compounds in which

with exception of.

The imidamide derivatives of formula (I) can, depending on the Substituents that occur as optical and / or geometric isomers. The present The present invention relates to both the various mixtures of isomers and pure isomers.

The new imidamide derivatives of the general formula (I) are obtained if ethanimidates of the formula (II)

in which
R and R ^{1 have} the meaning given above,
Q stands for oxygen or sulfur and
Z represents alkyl,
with amines of the formula (III)

in which
R ² and R ^{3 have} the meaning given above in the presence of a diluent.

The new imidamide derivatives of the general formula (I) have very pronounced ones biological properties and are mainly used to combat animal damage like insects, arachnids and especially nematodes that live in the land economy, in the forests, in the protection of supplies and materials as well as on hygiene sector occur, suitable.

The compounds according to the invention are generally defined by the formula (I). Preferred substituents or ranges of those mentioned in the above and below The radicals listed in formulas are explained below.

R preferably represents cyano or nitro.

R ¹ preferably represents hydrogen optionally substituted by halogen, cyano or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₄ alkyl, optionally monosubstituted to trisubstituted by identical or different halogen or C ₁ -C ₄ alkyl substi tuiert C ₃ -C ₆ cycloalkyl or for optionally monosubstituted to trisubstituted, identically or differently substituted, phenyl substituents which may be mentioned as substituents in R ⁶ .

R ² preferably represents hydrogen optionally substituted by halogen, cyano or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₄ -alkyl or represents optionally a fold to trisubstituted by identical or different manner by halogen or C ₁ -C ₄ alkyl substituted C ₃ -C ₆ cycloalkyl.

R ³ preferably represents the groupings

in which
R ⁴ and R ⁵ independently of one another are preferably hydrogen; for, where appropriate, by halogen, cyano or C ₁ -C ₄ -alkoxy-substituted C ₁ -C ₄ alkyl or optionally mono- to trisubstituted by identical or different halogen or C ₁ -C ₄ alkyl-substituted C ₃ -C ₆ - Cycloalkyl stand.

R ⁶ and R ^7, independently of one another, preferably represent phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl which are each mono- to pentasubstituted by identical or different substituents, where the following may be mentioned as substituents:
Hydroxy, amino, cyano, nitro, halogen; in each case optionally hydroxyl-, cyano- or halogen-substituted C ₁ -C ₄ alkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₄ -alkylamino and di- (C ₁ -C ₄₎ alkylamino; each optionally substituted by halogen C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylcarbonylamino, C ₁ -C ₄ alkyl thio, C ₁ -C _4- alkylsulfinyl and C ₁ -C ₄ -alkylsulfonyl; Aminocarbonyl, aminothiocarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di (C ₁ -C ₄ ) alkylamino carbonyl, aminosulfonyl, C ₁ -C ₄ alkylaminosulfonyl and di (C ₁ -C ₄ ) alkylaminosulfonyl ; as well as optionally by hydroxy, cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - Alkylsulfonyl and C ₁ -C ₄ haloalkyl, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ haloalkylthio, C ₁ - C ₄ haloalkylsulfinyl and C ₁ -C ₄ haloalkylsulfonyl each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine substituted phenyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzyl and phenylamino;
furthermore represent in each case monosubstituted to pentasubstituted, identically or differently substituted C ₃ -C ₁₂ -cycloalkyl or C ₅ -C ₁₂ -cyclo alkenyl, the following being mentioned as substituents:

Halogen, optionally substituted C ₁ -C ₄ alkyl, preferred substituents being: halogen, such as fluorine, chlorine, bromine, optionally substituted C ₂ -C ₆ cycloalkyl and, if appropriate, phenyl; furthermore C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy and C ₁ -C ₄ haloalkyl and C ₁ -C ₄ haloalkoxy each having 1 to 5 identical or different halogen atoms from the series fluorine, chlorine and bromine;
and for an optionally mono- to pentasubstituted, identically or ver differently substituted, saturated or partially unsaturated or unsaturated mono- or tricyclic nitrogen-free heterocycle having 4 to 10 carbon atoms and 1 to 3 identical or different heteroatoms, such as O and S atoms, the phenyl substituents mentioned for R ^{6 being} suitable as substituents.

R ⁸ preferably represents C ₁ -C ₄ -alkyl or phenyl and naphthyl which are monosubstituted to pentasubstituted by identical or different substituents, the phenyl substituents mentioned for R ^{6 being} suitable as substituents.

X preferably represents a single bond, each straight-chain or branched C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl or C ₂ -C ₆ -alkynediyl and for the groups -AO-, -AS-, -AO- A'-, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where
Alk preferably represents C ₁ -C ₄ alkyl and
A and A 'independently of one another are preferably straight-chain or branched C ₁ -C ₆ -alkanediyl.

Y preferably represents a single bond and the groupings -OA-, -O-A '' - O-, -O-A '' - S-, -O-A '' - SO-, -O-A '' - SO ₂ -, -O-A '' - O-A'- or -O-A '' - S-A'-, where
A and A 'have the preferred meaning given above.

A '' preferably represents straight-chain or branched (C ₂ -C ₄ ) alkanediyl having at least 2 carbon atoms between the heteroatoms.

The preferred definitions contain the proviso that for R = CN and R ² = H the compounds in which

with exception of.

R particularly preferably represents cyano or nitro.

R ¹ particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy; for in each case monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, methyl or ethyl, cyclopropyl, cyclopentyl and cyclohexyl or, if appropriate, monosubstituted to trisubstituted, identically or differently, phenyl, where the phenyl substituents mentioned for R ⁶ in Question come.

R ² particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or in each case optionally one to three times, the same or different, substituted by fluorine, chlorine, bromine, methyl or ethyl, cyclopropyl, cyclopentyl and cyclohexyl.

R ³ particularly preferably represents the groupings

in which
R ⁴ and R ⁵ independently of one another are particularly preferably hydrogen; for each methyl, ethyl, n- or i-propyl and n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, or for each optionally optionally up to three times, identically or differently by Fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclopentyl and cyclohexyl.

R ⁶ and R ⁷ independently of one another are particularly preferably in each case single to triple, identically or differently substituted phenyl, naphthyl, dihydronaphthyl and tetrahydronaphthyl, where the following are mentioned as substituents:
Cyano, nitro, amino, fluorine, chlorine, bromine; each optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino or dimethylamino; each optionally substituted with fluorine and / or chlorine, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl or ethylsulfonyl; Aminocarbonyl, aminothiocarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylamino carbonyl, aminosulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl and diethylaminosulfonyl; and in each case optionally by cyano, nitro, fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, difluoromethoxy or trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfyl, trifluoromethylsulfyl, trifluoromethylsulfyl, tri Phenylsulfinyl, phenylsulfonyl, benzyl or phenylamino;
furthermore for each optionally single to triple, identical or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl, optionally substituted cyclohexyl-C ₁ -C ₄ -alkyl, optionally substituted phenyl-C ₁ -C ₄ -alkyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy substituted cyclopentane, cyclohexane, cyclo pentene and cyclohexene;
and for an optionally mono- to pentasubstituted, identically or ver differently substituted, saturated or partially unsaturated or unsaturated mono- or bicyclic nitrogen-free heteroeye having 4 to 9 carbon atoms and 1 to 3 identical or different hetero atoms, such as O- and S atoms, the following being mentioned as substituents:

Cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, Methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, trifluoromethyl thio and dimethylamino.

R ^{8 is} particularly preferably methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R ^{6 being} suitable as substituents.

X particularly preferably stands for a single bond and for the groupings:
-CH ₂ -, - (CH ₂ ) ₂ -, - (CH ₂ ) ₃ -, - (CH ₂ ) ₄ -, -CH (CH ₃ ) -, -CH (C ₂ H ₅ ) -, -CH ( CH ₃ ) CH ₂ -, -CH ₂ CH (CH ₃ ) -, -CH (CH ₃ ) CH ₂ CH ₂ -, -C (CH ₃ ) ₂ -, -CH ₂ C (CH ₃ ) ₂ -, - CH ₂ CH (CH ₃ ) CH ₂ -, -CH (CH ₃ ) -CH (CH ₃ ) -, -CH (C ₂ H ₅ ) CH ₂ CH ₂ -;
-CH ₂ O-, -CH ₂ S-, - (CH ₂ ) ₂ O-, - (CH ₂ ) ₂ S-, -CH (CH ₃ ) CH ₂ O-, -CH (C ₂ H ₅ ) CH ₂ O-;
-CH ₂ OCH ₂ -, CH ₂ SCH ₂ -, -CH (CH ₃ ) CH ₂ OCH ₂ -, -CH (C ₂ H ₅ ) CH ₂ OCH ₂ -;
-CH = CH-, -C (CH ₃ ) = CH, -CH ₂ -CH = CH-, -CH ₂ -C (CH ₃ ) = CH-, -C∼C-, -CH ₂ -C∼C -, -CH (CH ₃ ) -C∼C-;
-CH ₂ -N (CH ₃ ) -, - (CH ₂ ) ₂ -N (CH ₃ ) -, - (CH ₂ ) ₃ -N (CH ₃ ) -, -CH ₂ -N (C ₂ H ₅ ) -, - (CH ₂ ) ₂ -N (C ₂ H ₅ ) -, - (CH ₂ ) ₃ -N (C ₂ H ₅ ) -, -CH ₂ -N (CH ₃ ) -CH ₂ -, - ( CH ₂ ) ₂ -N (CH ₃ ) -CH ₂ -, - (CH ₂ ) ₃ -N (CH ₃ ) -CH ₂ -, -CH ₂ -N (C ₂ H ₅ ) -CH ₂ -, - ( CH ₂ ) ₂ -N (C ₂ H ₅ ) -CH ₂ -, - (CH ₂ ) ₃ -N (C ₂ H ₅ ) -CH ₂ -.

Y particularly preferably represents a single bond and the groupings -OCH ₂ -, -O (CH ₂ ) ₂ -, -O (CH ₂ ) ₃ -, -O (CH ₂ ) ₄ -, -OCH (CH ₃ ) - , -OCH (C ₂ H ₅ ) -, -OCH (CH ₃ ) CH ₂ -, -OCH ₂ CH (CH ₃ ) -, -OCH (C ₂ H ₅ ) CH ₂ -, -OCH (CH ₃ ) CH ₂ CH ₂ -, -OCH (C ₂ H ₅ ) CH ₂ CH ₂ -, -OCH ₂ CH (CH ₃ ) CH ₂ -, -OCH ₂ CH ₂ CH (CH ₃ ) -, -OCH ₂ CH ₂ O- , -OCH ₂ CH ₂ S-, -OCH ₂ CH ₂ SO-, -OCH ₂ CH ₂ SO ₂ -, -OCH (CH ₃ ) CH ₂ O-, -OCH (C ₂ H ₅ ) CH ₂ O-, -OCH (CH ₃ ) CH ₂ S-, -OCH (C ₂ H ₅ ) CH ₂ S-, -OCH ₂ CH ₂ OCH ₂ -, -OCH ₂ CH ₂ SCH ₂ -, -OCH (CH ₃ ) CH ₂ OCH ₂ -, -OCH (CH ₃ ) CH ₂ SCH ₂ -, -OCH (C ₂ H ₅ ) CH ₂ OCH ₂ -, -OCH (C ₂ H ₅ ) CH ₂ SCH ₂ -.

The particularly preferred definitions contain the proviso that for R = CN and R ² = H the compounds in which

with exception of.

R very particularly preferably represents cyano or nitro.

R ¹ very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, cyclopropyl or phenyl.

R ² very particularly preferably represents hydrogen; Methyl, ethyl, n- or i-propyl or cyclopropyl.

R ³ very particularly preferably represents the groupings

in which
R ⁴ and R ⁵ independently of one another very particularly preferably for hydrogen; Methyl, ethyl, n- or i-propyl and cyclopropyl are available.

R ⁶ and R ⁷ independently of one another very particularly preferably represent phenyl or naphthyl which may be monosubstituted to trisubstituted identically or differently, the following being mentioned as substituents:
Cyano, nitro, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, trifluoromethyl, difluoromethyl , Trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino carbonyl and diethyl; and in each case optionally substituted by cyano, nitro, fluorine, chlorine, methyl, methoxy, methylthio, methylsulfinyl, methylsulfonyl, trifluoromethyl or trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl or trifluoromethylsulfonyl, phenyl, phenoxy, phenylthio, phenylsulfino, phenyl or phenylsulfyl;
furthermore represent cyclo pentane or cyclohexane which are optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, methyl, ethyl, i-propyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy;
and for the following heterocycles which may be monosubstituted to pentasubstituted by identical or different substituents:

where as (additional) substituents are mentioned:
Cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, trifluoromethyl or dimethylamino or optionally substituted phenyl, where the substituents for the phenyl radical are the substituents which are also under R ⁶ for the Phenyl radical are called.

R ⁸ very particularly preferably for methyl, ethyl, n- or i-propyl; n-, i-, s- or t-butyl or phenyl which is optionally monosubstituted to trisubstituted identically or differently, the phenyl substituents mentioned for R ^{6 being} suitable as substituents.

X very particularly preferably represents a single bond and the groupings: -CH ₂ -, - (CH ₂ ) ₂ -, - (CH ₂ ) ₃ -, -CH (CH ₃ ) -, -C (CH ₃ ) ₂ - , -CH ₂ C (CH ₃ ) ₂ -, -CH (CH ₃ ) CH ₂ -, -CH ₂ O-, -CH ₂ S-, - (CH ₂ ) ₂ O-, - (CH ₂ ) ₂ S -, -CH ₂ OCH ₂ -, CH ₂ SCH ₂ -, -C (CH ₃ ) ∼CH, -C∼C-, - (CH ₂ ) ₃ -N (CH ₃ ) -, - (CH ₂ ) ₃ -N (C ₂ H ₅ ) -, - (CH ₂ ) ₃ -N (CH ₃ ) -CH ₂ -, - (CH ₂ ) ₃ -N (C ₂ H ₅ ) -CH ₂ -.

Y very particularly preferably represents a single bond and the groupings -OCH ₂ -, -O (CH ₂ ) ₂ -, -O (CH ₂ ) ₃ -, -O (CH ₂ ) ₄ -, -OCH (CH ₃ ) -, -OCH (C ₂ H ₅ ) -, -OCH (CH ₃ ) CH ₂ -, -OCH (CH ₃ ) CH ₂ CH ₂ -, -OCH (C ₂ H ₅ ) CH ₂ CH ₂ -, -OCH ₂ CH ₂ O-, -OCH ₂ CH ₂ S-, -OCH ₂ CH ₂ SO-, -OCH ₂ CH ₂ SO ₂ -, -OCH (CH ₃ ) CH ₂ O-, -OCH (C ₂ H ₅ ) CH ₂ O-, -OCH (CH ₃ ) CH ₂ S-, -OCH (C ₂ H ₅ ) CH ₂ S-, -OCH ₂ CH ₂ OCH ₂ -, -OCH ₂ CH ₂ SCH ₂ -.

The very particularly preferred definitions contain the proviso that for R = CN and R ² = H the compounds in which

with exception of.  

Preferred compounds according to the invention are substances of the formulas (Ia) to (Ih):

in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , X and Y stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

The compounds of the above formula (Ib) are particularly emphasized.

Preferred compounds according to the invention are also substances of the formulas (IA) to (IW):

in which
R ³ , R ⁴ , R ⁵ and R ^{6 represent} the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

Preferred compounds according to the invention are also substances of the formulas (I-1) to (I-56)

in which
R ¹ , R ² , R ⁶ and R ⁷ stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.

The radicals listed above or listed in preferred areas definitions and explanations apply to the end products and to the initial and intermediates accordingly. These residual definitions can be thus also be combined as desired between the respective preferred areas.

According to the invention, preference is given to the compounds of the formula (I) in which a combination of the Be listed as preferred (preferred) interpretations are available.

According to the invention, particular preference is given to the compounds of the formula (I), in which a combination of the Be listed as particularly preferred above interpretations are available.  

The compounds of the formula are very particularly preferred according to the invention (I) in which a combination of the above is given as being particularly preferred meanings.

In the residue definitions listed above and below are hydrocarbons residues such as alkyl or alkenyl - also in combination with heteroatoms such as Alkoxy or alkylthio - if possible straight or branched.

The following connections are specifically mentioned:

Table 1

Compounds in Table 1 correspond to the general formula (Ib), in which R ¹ = CH ₃
R ² = H
C (R ⁴ , R ⁵ ) = CH ₂
XR ⁶ = as listed below:

Table 1 (continued)

Table 1 (continued)

Table 1 (continued)

Table 2

Compounds in Table 2 correspond to the general formula (Ib), in which
C (R ⁴ , R ⁵ ) = CH (CH ₃ )
R ¹ , R ² and XR ⁶ = as listed in Table 1.

Table 3

Compounds in Table 3 correspond to the general formula (Ib), in which
C (R ⁴ , R ⁵ ) = CH (C ₂ H ₅ )
R ¹ , R ² and XR ⁶ = as listed in Table 1.

Table 4

Compounds in Table 4 correspond to the general formula (Ib), in which
C (R ⁴ , R ⁵ ) = CH (C ₃ H ₇ -i)
R ¹ , R ² and XR ⁶ = as listed in Table 1.

Table 5

Compounds in Table 5 correspond to the general formula (Ib), in which
C (R ⁴ , R ⁵ ) = CH (C ₃ H ₇ -n)
R ¹ , R ² and XR ⁶ = as listed in Table 1.

Table 6

Compounds in Table 6 correspond to the general formula (Ib), in which
C (R ⁴ , R ⁵ ) = C (CH ₃ ) ₂
R ¹ , R ² and XR ⁶ = as listed in Table 1.

Tables 7-12

Compounds in Tables 7-12 correspond to the general formula (Ib), in which
R ¹ = C ₂ H ₅
R ² = H
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 13-18

Compounds in Tables 13-18 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -i
R ² = H
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 19-24

Compounds in Tables 19-24 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -n
R ² = H
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 25-30

Compounds in Tables 25-30 correspond to the general formula (Ib), in which
R ¹ =
R ² = H
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 31-36

Compounds in Tables 31-36 correspond to the general formula (Ib), in which
R ¹ = H
R ² = H
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 37-42

Compounds in Tables 37-42 correspond to the general formula (Ib), in which
R ¹ = H
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 43-48

Compounds in Tables 43-48 correspond to the general formula (Ib), in which R ¹ = H
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 49-54

Compounds in Tables 49-54 correspond to the general formula (Ib), in which
R ¹ = CH ₃
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 55-60

Compounds in Tables 55-60 correspond to the general formula (Ib), in which
R ¹ = CH ₃
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 61-66

Compounds in Tables 61-66 correspond to the general formula (Ib), in which
R ¹ = CH ₃
R ² = C ₃ H ₇ -i
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 67-72

Compounds in Tables 67-72 correspond to the general formula (Ib), in which
R ¹ = C ₂ H ₅
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 73-78

Compounds in Tables 73-78 correspond to the general formula (Ib), in which
R ¹ = C ₂ H ₅
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 79-84

Compounds in Tables 79-84 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -i
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 85-90

Compounds in Tables 85-90 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -i
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Table 91-96

Compounds in Tables 91-96 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -n
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 97-102

Compounds in Tables 97-102 correspond to the general formula (Ib), in which
R ¹ = C ₃ H ₇ -n
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 103-108

Compounds in Tables 103-108 correspond to the general formula (Ib), in which
R ¹ =
R ² = CH ₃
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Tables 109-114

Compounds in Tables 109-114 correspond to the general formula (Ib), in which
R ¹ =
R ² = C ₂ H ₅
C (R ⁴ , R ⁵ ) = as listed in Tables 1 to 6.
XR ⁶ = as listed in Table 1.

Table 115

Compounds in Table 115 correspond to the general formula (Ic), in which
R ¹ = CH ₃
R ² = H
YR ⁷ = as listed below:

Table 115 (continued)

Table 116

Compounds in Table 116 correspond to the general formula (Ic), in which
R ¹ = C ₂ H ₅
R ² = H
YR ⁷ = as listed in Table 115.

Table 117

Compounds in Table 117 correspond to the general formula (Ic), in which
R ¹ = C ₃ H ₇ -i
R ² = H
YR ⁷ = as listed in Table 115.

Table 118

Compounds in Table 118 correspond to the general formula (Ic), in which
R ¹ = C ₃ H ₇ -n
R ² = H
YR ⁷ = as listed in Table 115.

Table 119

Compounds in Table 119 correspond to the general formula (Ic), in which
R ¹ =
R ² = H
YR ⁷ = as listed in Table 115.

Table 120

Compounds in Table 120 correspond to the general formula (Ic), in which
R ¹ = H
R ² = H
YR ⁷ = as listed in Table 115.

Table 121

Compounds in Table 121 correspond to the general formula (Ic), in which
R ¹ = H
R ² = CH ₃
YR ⁷ = as listed in Table 115.

Table 122

Compounds in Table 122 correspond to the general formula (Ic), in which
R ¹ = H
R ² = C ₂ H ₅
YR ⁷ = as listed in Table 115.

Table 123

Compounds in Table 123 correspond to the general formula (Ic), in which
R ¹ = H
R ² = C ₃ H ₇ -i
YR ⁷ = as listed in Table 115.

Table 124

Compounds in Table 124 correspond to the general formula (Ic), in which
R ¹ = CH ₃
R ² = CH ₃
YR ⁷ = as listed in Table 115.

Table 125

Compounds in Table 125 correspond to the general formula (Ic), in which
R ¹ = CH ₃
R ² = C ₂ H ₅
YR ⁷ = as listed in Table 115.

Table 126

Compounds in Table 126 correspond to the general formula (Ic), in which
R ¹ = CH ₃
R ² = C ₃ H ₇ -i
YR ⁷ = as listed in Table 115.

Table 127

Compounds in Table 127 correspond to the general formula (Ic), in which
R ¹ = C ₂ H ₅
R ² = CH ₃
YR ⁷ = as listed in Table 115.

Table 128

Compounds in Table 128 correspond to the general formula (Ic), in which
R ¹ = C ₂ H ₅
R ² = C ₂ H ₅
YR ⁷ = as listed in Table 115.

Table 129

Compounds in Table 129 correspond to the general formula (Ic), in which
R ¹ = C ₃ H ₇ -i
R ² = CH ₃
YR ⁷ = as listed in Table 115.

Table 130

Compounds in Table 130 correspond to the general formula (Ic), in which
R ¹ = C ₃ H ₇ -i
R ² = C ₂ H ₅
YR ⁷ = as listed in Table 115.

Table 131

Compounds in Table 131 correspond to the general formula (Ic), in which
R ¹ = CH ₃
R ² =
YR ⁷ = as listed in Table 115.

The following compounds are preferred:

Table a

Table a (continued)

Table a (continued)

Table a (continued)

Table b

Table b (continued)

Table c

R ⁶ = as listed in table b, and additionally

Table d

R ⁶ = as listed in Table c.

Table e

Table f

R ⁶ = as listed in Table e.

Table g

Table g (continued)

Table h

The above-mentioned compounds according to the invention of the different formulas and in the individual tables may optionally be present as racemates, R or S isomers. If, for example, methyl N-cyanoethanimidate and 4-chloro-2-methylbenzylamine are used as starting materials, the course of the process according to the invention can be represented by the following reaction scheme:

Formula (II) provides a general definition of the ethanimide esters required as starting materials for carrying out the process according to the invention. In this formula, Z is preferably C ₁ -C ₄ alkyl, in particular methyl or ethyl.

The N-cyanoethanimidic acid esters are largely known (cf., for example, US 5,304,566 or J. Org. Chem. 28, 1963, 1816-1821) and / or by conventional methods Lich.

The N-nitro-ethanimidic acid esters are obtained by e.g. B. which correspond to the NO ₂ -free ethanimidates of the formula (II) nitrated in the usual way.

Which continue to be used as starting materials in the process according to the invention the amines of the general formula (III) are generally known compounds of organic chemistry or available in a generally known manner.  

The process according to the invention is preferably carried out in the presence of a diluent carried out. Alcohols, such as methanol, are preferably usable and ethanol; Nitriles such as acetonitrile or esters such as ethyl acetate. It is also possible to work in water or organic-aqueous mixtures if necessary.

The process according to the invention is preferably carried out in equimolar amounts; but it is also possible to start one or the other pro duct to use in excess.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 100 ° C, preferably between 20 ° C and 80 ° C.

The end products are worked up and isolated in a generally known manner and way.

The active ingredients are suitable for good plant tolerance and inexpensive warmth blood toxicity to control animal pests, especially insects, Arachnids and nematodes, which are used in agriculture, in forests, in stock and Material protection and in the hygiene sector. You can preferably can be used as pesticides. They are sensitive to normal and resi constant species and effective against all or individual stages of development. To the Pests mentioned above include:

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spp.  

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.

From the order of the Blattaria z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Phthiraptera z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frank1iniella accidentalis.

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix  cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, llyponomeuta padella, Plutella xylustella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ainbiguella, Homona magnanima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocepha1a, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp.,  Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the class of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursa phelenchus spp.

The compounds of the formula (I) according to the invention are particularly noteworthy with good nematicidal activity. For example, they can be used with use particularly good success to combat Meloidogyne incognita.

The active ingredients can be converted into the usual formulations, such as Lö solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble Che powder, granules, suspension emulsion concentrates, impregnated with active ingredient Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

In the corresponding application rates show the Ver some herbicidal effects.  

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-producing Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: z. B. stem and fractionate natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco; as emulsifying and / or foam-generating agents come into question: z. B. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

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

The active substance according to the invention can be so in its commercially available formulations as in the use forms prepared from these formulations in a mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, Acaricides, nematicides, fungicides, growth regulators or herbi ziden available. Insecticides include, for example, phosphoric acid esters, Carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms u. a.

Particularly cheap mixing partners are e.g. B. the following:  

Fungicides

Aldimorph, anipropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin,
Benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos, binapacrylic, biphenyl, bitertanol, blasticidin-S, bromuconazole, bupirimate, buthiobate,
Calcium polysulfide, capsimycin, captafol, captan, carbendazim, carboxin, carvone, quinomethionate (quinomethionate), chlobenthiazone, chlorfenazole, chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon, cufraneb, cymoxariil, cyphodaminolol, cypodaminazol, cypodinconol
Debacarb, dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithorphoxinodonine, dithorphononodine
Ediphenphos, Epoxiconazole, Etaconazole, Ethirimol, Etridiazole,
Famoxadone, Fenapanil, fenarimol, fenbuconazole, fenfuram, Fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, Fentinhydroxyd, ferbam, ferimzone, fluazinam, flumetover, fluoromide, fluquinconazole, flurprimidol, flusilazole, Flusul famid, flutolanil, flutriafol, folpet, fosetyl-Alminium , Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis, furmecyclox,
Guazatin,
Hexachlorobenzene, hexaconazole, hymexazole,
Imazalil, Imibenconazol, Iminoctadin, Iminoctadinealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
Kasugamycin, Kresoxim-methyl, copper preparations, such as: copper hydroxide, copper naphthenate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture,
Mancopper, Mancozeb, Maneb, Meferirnzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol,
Ofurace, Oxadixyl, Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
Paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen, pimaricin, piperalin, polyoxin, polyoxorim, probenazole, prochloraz, procymidon, propamocarb, propanosine sodium, propiconazole, propineb, pyrazophos, pyrifen, pyifenox, pyrroyilonil
Quinconazole, quintozen (PCNB),
Sulfur and sulfur preparations,
Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifliizamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, triflumizole, triforine, triticonazole,
Uniconazole,
Validamycin A, vinclozolin, viniconazole,
Zarilamid, Zineb, Zirain as well
DaggerG,
OK-8705,
OK-8801,
α- (1,1-dimethylethyl) -β- (2-phenoxyethyl) -1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-fluoro-b-propyl-1H-1,2,4-triazole-1-ethanol,
α- (2,4-dichlorophenyl) -β-methoxy-a-methyl-1H-1,2,4-triazole-1-ethanol,
α- (5-methyl-1,3-dioxan-5-yl) -β - [[4- (triftuormethyl) phenyl] methylene] - 1H-1,2,4-triazol-1-ethanol,
(5RS, 6RS) -6-hydroxy-2,2,7,7-tetramethyl-5- (1H-1,2,4-triazol-1-yl) -3-octanone,
(E) -a- (methoxyimino) -N-methyl-2-phenoxy-phenylacetamide,
{2-Methyl-1 - [[[1- (4-methylphenyl) ethyl] amino] carbonyl] propyl} carbamic acid 1-isopropyl ester
1- (2,4-dichlorophenyl) -2- (1H-1,2,4-triazol-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 - [(diiodinethyl) sulfonyl] -4-methyl-benzene,
1 - [[2- (2,4-dichlorophenyl) -1,3-dioxolan-2-yl] 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'-trifluoromethyl-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- (trifluoromethyl) phenyl] methyl] beramide,
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 [2,3-d] pyrimidine-5-carbonitrile,
2-aminobutane,
2-bromo-2- (bromomethyl) pentandinitrile,
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- [cyan [(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-cyan-N, N-dimethyl-5- (4-methylphenyl) -1H-imidazole-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 sulfate,
9H-xanthene-9-carboxylic acid 2 - [(phenylamino) carbonyl] hydrazide,
bis- (1-methylethyl) -3-methyl-4 - [(3-methylbenzoyl) -oxy] -2,5-thiophene dicarboxylate,
cis-1- (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol,
cis-4- [3- [4- (1,1-dimethylpropyl) phenyl-2-methylpropyl] -2,6-dimethylmorpholine hydrochloride,
Ethyl - [(4-chlorophenyl) azo] cyanoacetate,
Potassium hydrogen carbonate,
Methane tetrathiol 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-cyclohexane carboxamide.
N- (2,6-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-pyrimidinamine,
N- (4-hexylphenyl) -1,4,5,6-tetrahydro-2-pyrimidinamine,
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'-methoxymanimidamide,
N-formyl-N-hydroxy-DL-alanine sodium salt,
O, O-diethyl- [2- (dipropylamino) -2-oxoethyl] ethylphosphoramidothioate,
O-methyl-S-phenyl-phenylpropylphosphoramidothioate,
S-methyl-1,2,3-benzothiadiazole-7-carbothioate,
spiro [2H] -1-benzopyran-2,1 '(3'H) -isobenzofuran] -3'-one,

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, Octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Teclofta lam, copper sulfate and other copper preparations.  

Insecticides / acaricides / nematicides

Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Buto carboxim, Butylpyridaben,
Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, Chloethocarb, Chlorethoxyfos, Chlorfenvinphos, Chlorfluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocythrinothrinhrhrinhrinhrinhrinhrinhrine, Clofenin , Cyhexatin, cypermethrin, cyromazine,
Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Diazinon, DichIofenthion, Dichlorvos, Dicliphos, Dicrotophos, Diethion, Difluberizuron, Di methoat, Dimethylvinphos, Dioxathion, Disulfoton,
Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Ethoprophos, Etrimphos,
Fenamiphos, Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothxinfox, Fufionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufon
HCH, heptenophos, hexaflumuron, hexythiazox,
Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
Lambda cyhalothrin, lufenuron,
Malathion, Mecarbam, Mevinphos, Mesulfenphos, Metaldehyde, Methacrifos,
Methamidophos, methidathione, methiocarb, methomyl, metolcarb, milbemectin, monocrotophos, moxidectin,
Naled, NC 184, NI 25, Nitenpyram
Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos,
Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophhion, Pyrachlophin, Pyrachlophin, Pyrachlophin, Pyrachlophin Pyridaben, pyrimidifen, pyriproxifen,
Quinalphos,
RH5992,
Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Spinosad,
Tebufenozid, tebufenpyrad, tebupirimiphos, teflubenzuron, tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio methon, Thionazin, Thuringiensin, Tralometichoniazon, Triaromenoxtronium, Triaromenoxtronium, Triaromenoxtronium, Triaromoxhriazon
Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

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

When used as insecticides and Nematicides in their commercial formulations as well as in those from them Formulations prepared application forms mixed with synergists lie. Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.

The active ingredient content of the prepared from the commercially available formulations Application forms can vary widely. The drug concentration of the Application forms can range from 0.0000001 to 95% by weight of active ingredient; preferably are between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms Wise.

When used against hygiene and storage pests, the effect is noticeable fabric through an excellent residual effect on wood and clay as well as through a good stability to alkali on limed substrates.

The compounds according to the invention show at appropriate application rates also herbicidal properties or plant growth regulating action, such as. B. a defoliant effect.

The active compounds according to the invention act not only against plant, hygiene and Pests, but also against the veterinary sector animal parasites (ectoparasites) such as tortoise ticks, leather ticks, mite mites, Running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings and fleas. These parasites include:  

From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the subordinates Ainblycerina as well Ischnocerina e.g. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.

From the order Diptera and the subordinates Nematocerina as well Brachycerina e.g. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasteropliilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.

From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.

From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata e.g. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., RIiipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.  

From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compounds of the formula (I) according to the invention are also suitable for combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish so such as so-called experimental animals, such as B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) can be reduced so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as Collars, ear tags, tail tags, limb straps, halters, Mar marking devices etc.  

When used for cattle, poultry, pets etc., you can use the active ingredients in Formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000 times dilution, or as a chemical bath use.

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical materials to destroy.

The following are examples and preferably - but without limitation - Called insects:

Beetle like
Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearesces rugus, Lyctus pubescescus, Lyctus pubis linearis, Lyctus linearesces rug Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus
Skin wings like
Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
Termites like
Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniens is, Zootermopsis nevadensis, Coptotermes formosanus.

Bristle tails, such as Lepisma saccarina.

In the present context, technical materials include non-living ones Understand materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood and wood processing products and paints.

The one to be protected against insect attack is very particularly preferably Material around wood and wood processing products.

Among wood and wood processing products, which by the invention Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, Wooden windows and doors, plywood, particle board, carpentry or wood products, which are generally used in house construction or in carpentry.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, emulsions or pastes.

The formulations mentioned can be prepared in a manner known per se be, e.g. B. by mixing the active ingredients with at least one solution or Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, possibly desiccants and UV stabilizers and given if dyes and pigments and other processing aids.

The insecticidal agents or used to protect wood and wood-based materials Concentrates contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.  

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. In general however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.

An organic chemical solution serves as the solvent and / or diluent medium or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, used. As such volatile, Water-insoluble, oily and oily solvents become corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene used.

Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boiling range from 250 to 350 ° C, petroleum or aromatics with a boiling range from 160 to 280 ° C, Turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range of 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably α-monochloronaphthalene used.  

The organic semi-volatile oily or oily solvents with a ver Evaporation number above 35 and a flash point above 30 ° C, preferably above half 45 ° C, can be partly due to slightly or medium volatile organic chemical Solvents are replaced, with the proviso that the solvent mixture also an evaporation number above 35 and a flash point above 30 ° C preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come aliphatic containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, ester or the like. to use.

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersible or emulsifiable Synthetic resins and / or binding drying oils, in particular binders from or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physics Lish-drying binders based on a natural and / or synthetic resin turns.

The synthetic resin used as a binder can be in the form of an emulsion, dispersion or solution. Bitumen or bitumi can also be used as binders nous substances up to 10 wt .-% can be used. In addition, in itself  known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to at least one organic chemical binder an alkyd resin or modified alkyd resin and / or a drying vegetable Contain oil in the medium or in the concentrate. Are preferred according to the invention Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight.

The binder mentioned can be wholly or partly by a fixation medium (mixture) or a plasticizer (mixture) can be replaced. These additions should len volatilization of the active ingredients and crystallization or precipitators prevent. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally mixed with one or more of the above organic chemical solvents or diluents, emulsifiers and dispersants.

A particularly effective wood protection is achieved through industrial impregnation processes, e.g. B. vacuum, double vacuum or printing process.  

The ready-to-use agents can, if appropriate, still further insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Particularly preferred mixing partners can be insecticides, such as chlorpyriphos, Phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, Permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, Tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N- octylisothiazolin-3-one.

The manufacture and use of the active compounds according to the invention start out the following examples.  

Manufacturing examples

example 1

5.0 g (0.05 mol) of methyl N-cyanoethanimidate are added to 7.8 g (0.05 mol) of [R] -4-chloro-2-methylbenzylamine in 30 ml of methanol and the reaction mixture is left for 2 hours Stir room temperature. Then water is added, the precipitate which has separated out is filtered off and dried.
This gives 7.0 g (63% of theory) of [R] -N-cyano-N '- (4-chlorophenyl-eth-1-yl) ethane imidamide with a melting point of 125 ° C. and an angle of rotation [a] 20 | D = + 252.5 ° (CH ₃ OH).

Analogously or according to the general procedure, the following are Compounds according to the invention obtained:

Table A

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table A (continued)

Table B

Examples of use Example A Limit concentration test

Test nematode: Meloidogyne incognita
Solvent: 4 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

The active ingredient preparation is intimately mixed with the soil with the test nematodes is contaminated. The concentration of the active ingredient in the accessory plays a role practically no role, the decisive factor is the amount of active ingredient per Volume unit of soil, which is given in ppm (= mg / l). You fill the be traded soil in pots, seeds lettuce and keeps the pots at a greenhouse temperature of 25 ° C.

After three weeks, the lettuce roots are attacked by nematodes (root galls) examined and the efficiency of the active ingredient determined in%. The efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is ge is exactly as high as in the control plants in untreated, but in the same Wise contaminated soil.

In this test z. B. the connection of preparation example 1 in a exemplary drug concentration of 20 ppm a killing of 100%.

Claims (7)

1. imidamide derivatives of the general formula (I),
in which
R represents cyano or nitro,
R ¹ for hydrogen; optionally substituted alkyl, optionally substituted cycloalkyl or optionally substituted phenyl,
R ^{2 represents} hydrogen, optionally substituted alkyl or optionally substituted cycloalkyl and
R ³ for the groupings
stands,
in which
R ⁴ and R ^{5 are} independently hydrogen; optionally substituted alkyl or optionally substituted cycloalkyl,
R ⁶ and R ⁷ independently of one another represent optionally substituted aryl, in each case optionally substituted cycloalkyl and cycloalkenyl or an optionally substituted mono-, bi- or tricyclic, nitrogen-free heterocycle,
R ^{8 represents} alkyl or optionally substituted aryl,
X for a single bond, for each straight-chain or branched alkanediyl, alkenediyl, alkindiyl and for the groups -AO-, -AS-, -AO-A'-, -AS-A'-, -AN (Alk) - or -AN (Alk) -A'-, where part A is bonded to the carbon atom of the group -C (R ⁴ R ⁵ ) -XR ⁶ ;
Alk stands for alkyl and
A and A 'independently of one another represent straight-chain or branched alkanediyl and
Y for a single bond and the groupings -OA-, -O-A '' - O-, -O-A '' - S-, -O-A '' - SO-, -O-A '' - SO ₂ -, -O-A '' - O-A'- or -O-A '' - S-A'-, the O atom of this group always ver on the N atom of the basic structure of the formula (I) ver is knotting;
A and A 'have the meaning given above and
A '' represents straight-chain or branched alkanediyl having at least 2 carbon atoms between the hetero atoms,
with the proviso that for R = CN and R ² = H the compounds in which
with exception of. 2. A process for the preparation of the imidamide derivatives of the general formula (I) according to claim 1, characterized in that ethanimidates of the formula (II)
in which
R and R ^{1 have} the meaning given above,
Q stands for oxygen or sulfur and
Z represents alkyl,
with amines of the formula (III)
in which
R ² and R ^{3 have} the meaning given above in the presence of a diluent. 3. pesticides, characterized by a content of minde at least one imidamide derivative of the formula (I) according to claim 1. 4. Use of imidamide derivatives of the formula (I) according to Claim 1 for Pest control. 5. A method for controlling pests, characterized in that imidamide derivatives of the formula (I) according to claim 1 on pests and / or let their living space take effect. 6. Process for the preparation of pesticides, thereby ge indicates that imidamide derivatives of the formula (I) according to Claim 1 mixed with extenders and / or surfactants. 7. Use of imidamide derivatives of the formula (I) according to Claim 1 for Manufacture of pesticides.