JPH013160A - (2-cyano-2-oxyiminoacetyl)-amino acid derivative - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides novel (2-cyano-2-oximino-acetyl)-amino acid derivatives, several methods for their production, and agents for controlling pests, especially bactericides and fungicides. (fu
ngicide).

It is known that certain substituted 2-cyano-2-methoxyimino-acetamides have good fungicidal and fungicidal activity (e.g. European Patent Application Publication No. 0.201,
999 and German Patent Application No. 3,602,24
(See No. 3). However, the action of these compounds is not always completely satisfactory, especially when low amounts and concentrations are applied.

Novel general formula (I) In the formula, R1 is a group -A-COOR2 or -B -C0N
represents R3R', A represents an optionally substituted linear or branched alkylene chain, B represents an optionally substituted linear or branched alkylene chain, R2 represents a substituent halogen, hydroxyl, alkoxy, acyloxy, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocycle; or R2 is further optionally substituted represents optionally substituted cycloalkyl or optionally substituted cycloalkenyl, R3 represents hydrogen; or a substituent halogen, '/7
/, -COOR', -CONRIIRm, -NRT
IR", -OR", -3(0). RN represents acyl and optionally substituted alkyl with optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl in each case; or R3 is further optionally substituted in each case; R4 represents hydrogen, or a substituent noroken, cyano, -COOR', CON RI I RI I
+, -NR"R"', -0RIv, -3(0), R
”, 7 syl and in each case optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl; or R4 is further optionally substituted in each case represents an alkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or group -〇R1v, or A and R2 together with the atoms bonded to the nucleus form an optionally substituted ring; , B and R3 together with the atoms bonded to the nucleus crystal represent an optionally substituted ring, or R3 and R6 together with the nitrogen atom bonded to the nucleus crystal further represent a hetero represents an optionally substituted heterocyclic group containing atoms, R is a substituent halogen, -COOR', -CONRTl
RIll-OR'! 1, represents a substituted alkyl having an optionally substituted heterocycle other than acyl and azolyl; or R represents an optionally substituted cycloalkenyl; R1 is hydrogen or a substituent halogen; represents optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl in each case, R1+ and RN are the same or different, and hydrogen or a substituent halogen , -〇〇OR'', -CONR' RN and in each case optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl; or Ro and Rrr' Furthermore, it represents alkenyl, alkynyl or in each case optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocycle, or together with the nitrogen atom bonded to the nucleus may contain further heteroatoms. represents an optionally substituted heterocyclic group, R12 represents hydrogen, alkyl, aralkyl or acyl, and n represents a number of 0, ■ or 2, )-amino acid derivatives were discovered.

The compounds of formula (T) can occur in different geometric isomeric forms depending on the configuration of the substituents on the C═N group (E or Z
isomers).

If appropriate, the compounds have one or more asymmetric carbon atoms; thus they can also be in the form of optical isomers (D- and L-configuration) and have different It can be obtained by ratio.

Furthermore, general formula (I), where R1 is a group -A-C00R2 or -113-CO
NR3R'; A represents a linear or branched alkylene chain that may be optionally substituted; B represents a linear or branched alkylene chain that may be optionally substituted; R2 represents a substituent halogen, hydroxyl, alkoxy, acyloxy, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocycle: or R2 is further optionally substituted. cycloalkyl optionally substituted or cycloalkenyl optionally substituted; R3 represents hydrogen; or a substituent halogen, cyano, -COOR', -CONR'' R11, -NRII
R", -OR", -3(0), R", acyl and optionally substituted alkyl with optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl in each case; or R3 represents optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocycle, and R4 represents hydrogen, or the substituents halogen, cyano, - COOR', -CONR"R", -NRIIR
I'', -OR'', -5(0), R'', acyl as well as optionally substituted aryl, heterocycle, cycloalkyl or cycloalkenyl in each case; or R4 may further represent each represents an optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or group -0RKI, or A and R2 are atoms bonded to the nucleus crystal; B and R together with the atoms bonded to the nucleus represent an optionally substituted ring; or B and R together with the atom bonded to the nucleus represent an optionally substituted ring; Together with the nitrogen atom bonded to the crystal, R represents an optionally substituted heterocyclic group which may further contain a heteroatom, R is a substituent halogen, -COOR', -CONRn
Rm, -〇R111! , represents a substituted alkyl having an optionally substituted heterocycle other than acyl and azolyl; or R represents an optionally substituted cycloalkenyl; R1 is hydrogen or a substituent halogen and each represents optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl, RII and RXI are the same or different, and hydrogen or a substituent halogen, −
c.

OR'', -CONR' R12 and in each case optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl; or RII and Rm further represent alkenyl, alkynyl or represents an optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocycle in each case or optionally substituted which together with the nitrogen atom bonded to the nucleus may further contain a heteroatom; a novel (2-cyano-2-oxyiminoacetyl)-, which represents an optional heterocyclic group, Roll represents hydrogen, alkyl, aralkyl or acyl, and n represents a number of O, I or 2.
The amino acid derivative is a) 2-cyano-2-oximino-acetate of the formula (II) "Siri-tJK", where R has the abovementioned meaning and R5 represents alkyl, if appropriate diluted. in the presence of an agent and, if appropriate, a base, with an amine of the formula (III) R1-NH, (III) in which R1 has the meaning given above: b) - of the formula (IV) in which R has the abovementioned meaning, in the presence of a catalyst, if appropriate, and an acid binder, if appropriate, in the presence of a diluent, React with the amine of the formula % formula % () where R1 has the above meaning; C) - formula (V) where M is hydrogen, an alkali metal ion, a protonated tertiary base or represents quaternary ammonium, and R1 has the abovementioned meaning, a 2-cyano-2-oximino-acetamide of formula (Vl) R -X (Vl) in which X represents a halogen or sulfonyloxy group and R has the above meaning; d) -Formula (■) where BSR and R5 are the above-mentioned Reacting a substituted acetylamino acid ester of formula (■), where R3 and R6 have the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of a base. e) - carboxyl-activated acetyl- of formula (II) in which R has the meaning given above and Q represents A or B, the latter having the meaning given above; Amino acids, if appropriate, in the presence of a catalyst and, if appropriate, in the presence of an acid binder and, if appropriate, a diluent, are prepared with the formula %formula%(), where Y represents an R20- or R3R'N- group; , wherein R2, R3 and R4 have the meanings given above: f) - 2-cyano-2-oximino-acetic acid of formula (XI), in which R has the meanings given above. ammonium salt of formula (XI[)R'', if appropriate in the presence of a diluent.
CH= O(XI[) in which the R6-CH- group represents the above meaning of A or B;
' with the isonitrile of formula (IV), in which R has the meaning given above; g) - in the presence of a catalyst, if appropriate or react with an isocyanate of the formula (XIV) R'-NCO(XIV) in which R1 has the abovementioned meaning; or h)--in the presence of a diluent if appropriate;
X V) The 2-cyano-2-oximino-acetamide of the formula, in which R has the abovementioned meaning, is reacted with a base, if appropriate in the presence of a diluent, and the resulting salt is reacted directly or, if appropriate, It has been found that by reacting, after intermediate isolation, if appropriate in the presence of a diluent, with a compound of the formula %formula %() in which R1 and X have the meanings given above. .

Finally, it has been found that new (2-cyano-2-oxyiminoacetyl)-amino acid derivatives have particularly strong fungicidal and fungicidal properties. Surprisingly, the compounds according to the invention are closely related structurally and/or from the point of view of their action to previously known substituted 2-cyano-
Shows more effective action than 2-methoxyiminoacetamide. The materials according to the invention thus represent a flourishing of the field.

In the following text, unless stated otherwise, all aliphatic groups such as alkyl, alkoxy, etc., by themselves or in combination such as alkoxyalkyl, can be straight-chain or branched, and likewise can be straight-chain or branched. The ring system may optionally be substituted with 1 to 5, particularly preferably 1 to 3 or particularly preferably 1 or 2, identical or different substituents.

Formula (I) provides a general definition of the (2-cyano-2-oxyiminoacetyl)-amino acid derivatives according to the invention.

Preferred ones are formula (I) in which R1 is a group -A-CO
represents OR2 or -B-CONR3R', A represents a straight-chain or branched alkylene having 1 to 4 carbon atoms, and B represents a straight-chain or branched chain having 1 to 4 carbon atoms; R2 represents an optionally substituted linear or branched alkyl having 1 to 6 carbon atoms, and the substituents that may be mentioned include /% Rogeken and optionally halogen, phenyl, optionally substituted with 1 to 5 identical or different substituents from the group consisting of alkyl and alkoxy, in each case having 1 to 4 carbon atoms, and cyclo, having 3 to 6 carbon atoms; Alkyl; or R2 more preferably has 3 to 6 carbon atoms and optionally 1 to 4 carbon atoms;
The same or different alkyl substituents 1 to 5 having
represents cycloalkyl optionally substituted with
or having 5 to 7 carbon atoms, and optionally 1 to 7 carbon atoms;
4 identical or different alkyl substituents 1-
represents a cycloalkenyl optionally substituted with 5, R3 further represents hydrogen, or a straight chain having 1 to 4 carbon atoms and optionally substituted with 1 or 2 substituents represents a branched or branched alkyl,
Substituents that can be mentioned include halogen, cyano, -GO
OR', -CONRIIRI'', -NRIIR',
-OR'', -3(O). R117, with 1 to 5 identical or different substituents from the group consisting of acyl having 2 to 9 carbon atoms, optionally halogen and alkyl having 1 to 4 carbon atoms; phenyl, optionally substituted, from the group consisting of alkylenes and alkoxys having 1 to 3 heteroatoms, in particular nitrogen, oxygen or sulfur, and optionally halogen and in each case 1 to 4 carbon atoms; 5- or 6-membered heterocyclic radicals optionally substituted with 1 to 5 identical or different substituents, and optionally 1 to 5 identical or different alkyl substituents having in each case 1 to 4 carbon atoms; 3 to 6 carbon atoms optionally substituted with 5
and cycloalkenyl having 5 to 7 carbon atoms; or R3 further represents in each case straight-chain or branched alkenyl or alkynyl having 2 to 6 carbon atoms; represents cycloalkenyl having 5 to 7 carbon atoms and optionally substituted with 1 to 5 identical or different alkyl substituents having 1 to 4 carbon atoms, or cycloalkenyl having 5 to 7 carbon atoms;
~6 substituents, and optionally the same or different substituents 1
Cycloalkyl which may be substituted with ~5 atoms; possible substituents include halogen, alkyl and alkoxy having 1 to 4 carbon atoms in each case, cyano, amino, carbamoyl, alkylamino having 1 to 4 carbon atoms in each alkyl moiety,
dialkylamino, alkylcarbamoyl and dialkylcarbamoyl, alkoxycarbonylamino with 1 to 4 carbon atoms in the alkoxy moiety, 5 or 6 carbon atoms in the cycloalkyl moiety and 1 carbon atom in the straight-chain or branched alkyl moiety phenyl and pyrrolidone optionally substituted with 1 to 5 identical or different substituents from the group consisting of cycloalkyl and cycloalkylalkyl having ~4 and halogen and alkyl having 1 to 4 carbon atoms; Is there; or R?
3 optionally also halogen, alkyl and alkoxy having in each case 1 to 4 carbon atoms and halogenoalkyl and halogenoalkoxy having I or 2 carbon atoms and 1 to 5 identical or different halogen atoms in each case phenyl optionally substituted with 1 to 5 identical or different substituents from the group consisting of, or having 1 to 3 identical or different heteroatoms, and optionally identical or different substituents Represents a 5- or 6-membered heterocyclic group which may be substituted with 1 to 5 members, and substituents that may be mentioned include halogen, mercapto,
phenyl and straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl having 1 to 4 carbon atoms per alkyl moiety, in which R4 has the meaning of R3 or polycyclic 21 represents a straight chain having 1 to 4 carbon atoms; B represents a branched or branched alkylene chain;
and R3 together with the atoms bonded to the skeleton represent a ring of the formula, where 22 represents a linear or branched alkylene chain having 1 to 4 carbon atoms, and Z3 represents hydrogen or represents alkyl having 1 to 4 carbon atoms, or R3 and R4 together with the nitrogen atom bonded to the skeleton have 1 to 3 other identical or different heteroatoms, and optionally the same or represents a 1.2- or 3-ring heterocyclic group which may be substituted with 1 to 5 different substituents, or a spiro-heterocyclic group, in which case the substituents that may be mentioned include, in each case, straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 6 carbon atoms,
Hydroxyl and oxo groups, straight-chain or branched alkenyl having 2 to 4 carbon atoms, hydroxycarbonyl, straight-chain or branched alkoxycarbonyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety , carbamoyl, in each case 1 to 1 carbon atom in each alkyl moiety
Identical or different from the group consisting of alkyl- and dialkylcarbamoyl having 4 and optionally halogen in each case and straight-chain or branched alkyl and alkoxy having 1 to 4 carbon atoms in each case phenyl optionally substituted with 1 or 2 substituents and phenylalkyl having 1 to 4 carbon atoms in the linear or branched alkyl moiety, and R having 1 to 6 carbon atoms; and represents a linear or branched alkyl substituted with 1 or 2 substituents, and substituents that may be mentioned include halogen, -COOR', -
CON RI I RI I +, -〇RN1 Other than acyl and azoyl having 2 to 9 carbon atoms, heteroatoms, such as in particular nitrogen, oxygen and 1 to 3 sulfur atoms, and optionally halogen and 1 carbon atom the same or different substituents from the group consisting of alkyl having ~4 1~
is a 3 to 6 membered heterocycle optionally substituted with 5; or R more preferably has 5 to 7 carbon atoms;
and represents cycloalkenyl optionally substituted with 1 to 5 identical or different substituents from the group consisting of alkyl having 1 to 4 carbon atoms, R1 being hydrogen or having 1 to 6 carbon atoms represents a straight-chain or branched alkyl, where RTl is hydrogen, a straight-chain or branched alkyl having 1 to 6 carbon atoms, a carbon atom in the straight-chain or branched alkyl moiety; represents phenylalkyl having 1 to 4 carbon atoms and optionally substituted with 1 to 5 identical or different substituents; possible substituents include halogen, in each case 1 to 5 carbon atoms;
alkyl and alkoxy having ~4 and halogenoalkyl and halogenoalkoxy having in each case 1 or 2 carbon atoms and 2 to 5 identical or different halogen atoms; or RII' further in each case each alkyl moiety represents alkoxycarbonylalkyno-carbaniylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having 1 to 4 carbon atoms or 3 to 6 carbon atoms;
cycloalkyl, optionally substituted with a straight-chain or branched alkyl having 1 to 4 carbon atoms, R1 is hydrogen, and a straight chain having 1 to 6 carbon atoms or a straight-chain or branched alkyl moiety having 1 to 4 carbon atoms and optionally substituted with 1 to 5 identical or different substituents; phenylalkyl, in which possible substituents on phenyl include the substituents on phenyl listed for R1+; alkoxycarbonylalkyl, carbamoylalkynoalkylcarbamoylalkyl or dialkylcarbamoylalkyl having from 3 to 6 carbon atoms and optionally having from 1 to 4 carbon atoms; represents cycloalkyl which may be substituted with alkyl of represents phenylalkyl having 1 to 4 atoms and optionally substituted with 1 to 5 same or different substituents, in which case possible substituents on phenyl include R or RN further represents acyl having 2 to 9 carbon atoms and n is 011
Or it represents the number 2.

Particularly preferred (2-cyano-2=oxyiminoacetyl)-amino acid derivatives of the general formula (I) are those in which R1 is a group -A-CO
represents OR2 or -B-CONR3R', and A is a group -
CH2-1-CH(CH3)- or -CH2CH2-
, B represents a group -CH2=36- -, -CH(CH3)- or -CH2CH2-, R2 represents a linear or branched alkyl having 1 to 4 carbon atoms, and R3 represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms and optionally being substituted with 1 or 2 identical or different substituents, in which case Substituents that can be mentioned include halogen, cyano, -COOR',
-CONR"R", -NR"R", -OR", -3
(○), RN, acyl having 2 to 9 carbon atoms, optionally substituted with 1 to 3 identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms phenyl, straight-chain or branched alkyl having 1 to 3 identical or different heteroatoms, in particular nitrogen, oxygen and sulfur, and optionally halogen and in each case 1 to 4 carbon atoms; and a 5- or 6-membered heterocyclic group optionally substituted with 1 to 3 identical or different substituents from the group consisting of alkoxy,
and cycloalkyl having 3 to 6 carbon atoms, optionally substituted in each case by straight-chain or branched alkyl having 1 to 4 carbon atoms, and cycloalkyl having 5 to 7 carbon atoms. Is there a cycloalkenyl; or R
3 very particularly preferably represents in each case straight-chain or branched alkenyl or alkynyl having 2 to 6 carbon atoms or optionally substituted having 3 to 6 carbon atoms. cycloalkyl; substituents which may be mentioned include halogen, in each case 1 to 1 carbon atoms;
Straight-chain or branched alkyl and alkoxy, cyano, amino, carbamoyl, in each case straight-chain or branched, having from 1 to 4 carbon atoms in each alkyl moiety; Chain-like alkylamino, dialkylamino, alkylcarbamoyl and dialkylcarbamoyl, alkoxycarbonylamino having 1 to 4 carbon atoms in the straight-chain or branched alkoxy moiety, in each case 5 carbon atoms in the cycloalkyl moiety or cycloalkyl and cycloalkylalkyl having 6 and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, and optionally halogen and 1 carbon atom
phenyl and pyrrolidone optionally substituted with 1 to 3 identical or different substituents from the group consisting of alkyl having ~4; or R3 is even more particularly preferably optionally halogen, in each case Consisting of straight-chain or branched-chain alkyls and alcoquines having 1 to 4 carbon atoms and halogenoalkyl and halogenoalkoxy having in each case 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms represents phenyl, optionally substituted with 1 to 3 identical or different substituents from the group, or represents a heteroatom, e.g.
In particular, it represents a 5- or 6-membered heterocyclic group having 1 to 3 nitrogen, oxygen or sulfur groups and optionally being substituted with the same or different substituents X to 3; Substituents which may be mentioned for the cyclic radicals include halogen, mercapto, phenyl and straight-chain or branched alkyl having 1 to 4 carbon atoms per alkyl, alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl. Yes, and R4 also has the meaning of R3,
or represents a polycyclic carbocyclic group or group -○RN,
or A and R2 together with the atoms bonded to the nucleus crystal represent a 5- or 6-membered ring of the formula optionally substituted with alkyl having 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms; , B and R3 together with the atoms bonded to the core crystal represent a 5- to 7-membered ring of the formula optionally substituted with alkyl having 1 to 4 carbon atoms, preferably 1 or 2 carbon atoms; , or a 1, 2 or 3 cyclic heterocyclic or spiro-heterocyclic group in which R3 and R4 together with the nitrogen atom bonded to the nucleus may optionally be substituted with 1 to 5 of the same or different substituents. Heterocyclic groups which represent cyclic groups and which may be mentioned include oxazolidine, pyrrolidine, imidazolidine, piperidine, piperazine, morpholine, thiomorpholine, ■,3-oxazane and l,3
-diazanes; these heterocyclic radicals can optionally be fused to one or two benzene or cyclohexane rings in each case, or can optionally be bridged with methylene or ethylene, with all heterocyclic groups Among the substituents which may be mentioned are straight-chain or branched alkyl or alkoxy having in each case 1 to 4 carbon atoms, cycloalkynoyl groups having 3 to 6 carbon atoms, hydroxyl and oxo groups, carbon Straight-chain or branched alkenyl having 2 to 4 atoms, hydroxycarbonyl, 1 carbon atom in the straight-chain or branched alkyl moiety
alkoxycarbonyl having ~4, carbamoyl,
Alkyl- and dialkylcarbamoyls having in each case 1 to 4 carbon atoms in each alkyl moiety and in each case 710ken and in each case 1 to 4 carbon atoms;
phenyl and straight-chain or branched alkyl optionally substituted with one or two identical or different substituents from the group consisting of straight-chain or branched alkyl having 4 and alkoxy; 1 to 4 carbon atoms in the part
phenylalkyl having 1 to 1 carbon atom;
4-substituted straight-chain or branched alkyl, examples of suitable substituents which may be mentioned in this case include halogen, -COOR', -CONR''RIn, -
OR” is a heterocyclic group of the formula acyl having 2 to 9 carbon atoms and optionally substituted with 1 to 3 identical or different alkyl substituents having 1 or 2 carbon atoms, or R optionally further comprises a methyl substituent 1-
represents cyclohexenyl or cyclopentenyl optionally substituted with 3, R1 represents a linear or branched alkyl having 1 to 4 carbon atoms, R1
represents hydrogen, linear or branched alkyl having 1 to 4 carbon atoms, or benzyl or phenethyl, which in each case may optionally be substituted with 1 to 3 identical or different substituents; Among the substituents on phenyl which may be mentioned in each case are fluorine, chlorine, methyl, methoxy and trifluoromethyl; alkoxycarbonylalkyl having 1 or 2 carbon atoms, carbamoylalkyl having 1 or 2 carbon atoms in the alkyl moiety or in each case alkylcarbamoylalkyl or dialkylcarbamoylalkyl having 1 or 2 carbon atoms in each alkyl moiety; or cycloalkyl having 3 to 6 carbon atoms and optionally substituted with 1 to 3 identical or different substituents from the group consisting of methyl and ethyl, and R1 means R1+ and R
N represents hydrogen, linear or branched alkyl having 1 to 4 carbon atoms, or benzyl or 7-enethyl, which in each case may optionally be substituted with 1 to 3 identical or different substituents; , substituents on phenyl that may be mentioned include fluorine, chlorine, methyl, methoxy and trifluoromethyl; or RN further represents acyl having 2 to 9 carbon atoms and n is 0, l
Or it represents the number 2.

Particularly preferred (2-cyano-2-oxyiminoacetyl)-amino acid derivatives of general formula (I) include (A) R' is a group -B
-Co-NR3R', B is a group -CH2-1-C
Represents H(CH3)- or -CH2CH2-, R3
represents hydrogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms, Ri represents hydrogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms, R represents substituted alkyl having 1 or 2 carbon atoms, and possible substituents include halogen, alkylcarbonyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, Group-COO
R′1-CONRIllR11′ and -OR” and represents a heterocyclic group of the formula; or R is more particularly preferably optionally substituted with 1 to 3 methyl substituents.
-represents cyclohexenyl; R1 is methyl, ethyl,
n- or i-propyl or n-1l-1sec-
or t-butyl, RtI and Rm are the same or different, and hydrogen, methyl, ethyl, n- or 1-propyl, or the same or different substitutions optionally having chlorine and methyl as substituents; represents benzyl optionally substituted with 1 to 3 radicals or represents alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, in each case representing 1 or 2 carbon atoms in each alkyl moiety; represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having 2 or cyclohexyl optionally substituted with 1 to 3 methyl substituents, and R is hydrogen, 1 or 2 carbon atoms; or benzyl optionally substituted with 1 to 3 identical or different substituents, in which case substituents on phenyl which may be mentioned include fluorine, chlorine and methyl; (B) R' represents a group -B-〇〇-NR3R', and B represents a group -CH2-1-CH(CH8)- or -CH2CH
2-, R3 is hydrogen, straight-chain or branched alkyl having 1 to 4 carbon atoms, or 1 to 4 carbon atoms;
represents an alkyl group having 1 or 2 substituents, and examples of the substituents include chlorine, hydroxyl, and a straight or branched alkyl moiety having 1 to 1 carbon atoms. alkylcarbonyloxy having 4;
1 to 1 carbon atom in the straight or branched alkyl moiety
alkylcarbonyl having 4 carbon atoms, alkoxy and alkylthio having 1 or 2 carbon atoms in each case and optionally phenyl optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine and methyl; , 2-furyl, 2-pyridyl, 1-morpholino, cyclopropyl and cyclohexyl; or R3
more particularly preferably represents allyl or propargyl, 1-cyclohexenyl or cyclohexyl substituted with 1 to 3 identical or different substituents, in which case the possible substituents include chlorine. , methyl, ethyl, methoxy, cyano, amino, alkyl-, in each case with 1 or 2 carbon atoms in each alkyl moiety, and dialkylamino, carbamoyl, in each case with 1 or 2 carbon atoms in each alkyl moiety alkyl- and dialkylcarbamoyl having , cyclohexyl, cyclohexylalkyl having 1 or 2 carbon atoms in the alkyl part, and 1-pyrrolidine-
2-one; or also R3 particularly preferably represents phenyl, optionally in each case optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine and methyl; represents 2-pyridyl or 2-pyrimidinyl optionally substituted with 1 to 3 methyl substituents or optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine, methyl and methoxy; represents 2-benzothiazolyl, which may be 1,2
．． 1-) 1,2,4-thiadiazol-5, which represents lyazol-3-yl or is optionally substituted with phenyl;
-yl or optionally mercapto, straight-chain or branched alkyl having 1 to 4 carbon atoms and in each case straight-chain or branched alkyl having 1 to 4 carbon atoms; optionally substituted with 1 to 3 identical or different substituents from the group consisting of alkylthi, alkylsulfinyl and alkylsulfonyl,
3. Represents 4-thiadiazol-5-yl or represents a group R4 represents an alkyl having 1 to 3 carbon atoms and substituted with 1 or 2 substituents, and the substituents that may be mentioned in this case The radicals include chlorine, hydroxyl, alkylcarbonyloxy having 1 to 4 carbon atoms in the straight or branched alkyl moiety, and 1 to 4 carbon atoms in the straight or branched alkyl moiety. Identical or different substituents 1 to 1 from the group consisting of alkylcarbonyl, alkoxy and alkylthio having in each case 1 or 2 carbon atoms, and optionally chlorine and methyl.
Phenyl optionally substituted with 3, 2-furyl, 2
-pyridyl, 1-morpholino, cyclopropyl and cyclohexyl: or R4 more particularly preferably represents allyl or propargyl, ■-cyclohexenyl, identical or different substituents 1 to 3;
represents cyclohexyl substituted with , substituents which may be mentioned include chlorine, methyl, ethyl, methoxy, cyano, amino, alkyl-, in each case having 1 or 2 carbon atoms in each alkyl moiety; dialkylamino, carbamoyl, alkyl- and dialkylcarbamoyl having in each case 1 or 2 carbon atoms in each alkyl moiety, cyclohexylalkyl having 1 or 2 carbon atoms in the cyclohexylalkyl moiety and 1-pyrrolidin-2-one Is there; or is there R?
It particularly preferably represents phenyl, optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine and methyl, or in each case optionally substituted with 1 to 3 methyl substituents. 2-pyridyl or 2-pyrimidinyl, optionally substituted with phenyl, or 2-thiazolyl, optionally substituted with phenyl, the same or different substituents 1 from the group consisting of chlorine, megul and methoxy; 2-benzothiazolyl optionally substituted with ~3, 2, 2,4-triazol-3-yl, 1,2,4-thiadiazol-5- optionally substituted with phenyl or
optionally mercap), straight-chain or branched alkyl having 1 to 4 carbon atoms and in each case straight-chain or branched alkylthio having 1 to 4 carbon atoms, 1 represents alkylsulfinyl and alkylsulfonyl or represents a group or R4 is more particularly preferably the same or different substituents 1 from the group consisting of hydroxyl, alkoxy having 1 or 2 carbon atoms, optionally chlorine and methyl; represents benzylokine optionally substituted with ~3, or represents 1-adamantyl, 2-norbornyl, ■- or 2-decalyl or 1- or 2-tetralyl; R has 1 or 2 carbon atoms Represents substituted alkyl, and examples of substituents that may be mentioned include halogen and carbon atoms 1 to 4 in the alkyl moiety.
alkylcarbonyl having groups -COOR', -
CONR"RII' and OR" and i: is a heterocyclic group of the formula 1; or R is more particularly preferably J-cyclo optionally substituted in each case with 1 to 3 methyl substituents; represents hexenyl, R1 is methyl, ethyl, n- or 1-propyl or n-1i-
1sec- or t-butyl, R■ and RI
I' are the same or different, and hydrogen, methyl, ethyl, n- or 1-propyl,
represents benzyl optionally substituted with 1 to 3 identical or different substituents with chlorine and methyl as substituents; or represents alkoxycarbonylalkyl having J or 2 carbon atoms in each alkyl moiety; , in each case carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having 1 or 2 carbon atoms in each alkyl moiety, or cyclohexyl optionally substituted with 1 to 3 methyl substituents; Expression and BN
represents hydrogen, alkyl having 1 or 2 carbon atoms, or benzyl optionally substituted with 1 to 3 of the same or different substituents, and substituents on phenyl that may be mentioned include fluorine, chlorine, and methyl; (C)R' represents a group -B-Co-NR3R3 and B represents a group -CH2-1-CH(CH3)- or -CH2CH
2-, and R3 and R4 together with the nitrogen atom bonded to the nucleus represent a 1.2- or 3-ring heterocyclic or spiro-heterocyclic group of formula CH3, where 2 is oxygen or represents CH2 group
Z4 represents hydroxyl, methoxy, ethoxy, amino, methylamino, ethylamino, dimethylamino, or ethylmethylamino, and m is 0. l represents a number of 2.3 or 4, p represents a number of 0.1 or 2, and q represents a number of 0.1.2 or 3, and R has 1 or 2 carbon atoms Represents substituted alkyl, and substituents that may be mentioned include halogen, alkylcarbonyl having 1 to 4 carbon atoms in the linear or branched alkyl moiety, -C○○R', -CON
RTIR]II%OR'' and the formula represents 1-cyclohenocenyl optionally substituted with 1 to 3 methyl substituents, R1 is methyl, ethyl, n- or 1-propyl or n -1i-1sec- or t
- butyl, Rn and R1 are the same or different and represent hydrogen, methyl, ethyl, n- or i-propyl, or optionally have chlorine and methyl as substituents, the same or different substituents 1 represents benzyl optionally substituted with ~3 or represents alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, in each case 1 or 2 carbon atoms in each alkyl moiety; represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having , or represents cyclohexyl optionally substituted with 1 to 3 methyl substituents, and RN represents hydrogen, 1 or 2 carbon atoms; alkyl or benzyl optionally substituted with 1 to 3 identical or different substituents, with possible substituents on phenyl being fluorine, chlorine and methyl; or (D) R' represents a group -A-COOR2 t) L, A represents a group -
CH2-1-CH(CH3)- or -CH2CH2-
, R2 is methyl or ethyl, R is substituted alkyl having 1 or 2 carbon atoms, and possible substituents include halogen, straight-chain or branched 1 to 4 carbon atoms in the alkyl part of
Alkylcarbonyl having , =GOOR', -CO
There are also heterocyclic radicals of the formula NR"RI I I, ORIV; R more particularly preferably represents l-cyclohexenyl, optionally substituted in each case with 1 to 3 methyl substituents; , R1 is methyl, ethyl, n- or i-propyl or n-1l-1se
represents C- or t-butyl, R1+ and R1' are the same or different, and hydrogen, methyl,
represents ethyl, n- or 1-propyl, or represents benzyl optionally substituted with 1 to 3 identical or different substituents with chlorine and methyl as substituents, or represents a carbon atom in each alkyl moiety; represents alkoxycarbonylalkyl having 1 or 2 or in each case 1 or 2 carbon atoms in each alkyl moiety;
represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having , or represents cyclohexyl optionally substituted with 1 to 3 methyl substituents, and RN has hydrogen, 1 or 2 carbon atoms Alkyl or benzyl optionally substituted with 1 to 3 identical or different substituents; substituents on phenyl which may be mentioned are fluorine, chlorine and methyl.

For example, (E)-2-cyano-2-(I-
When using ethyl butyloquine (polonylmethoxyimino)-ethyl acetate and Nα-glycyl-prolinamide hydrobromide, the route of step (a) according to the invention can be represented by the following formula: 0NH2 For example, as starting material chloride (E )-2-cyano-2-(
When using 2-furylmethoxyimino)-acetyl and N-glycyl-aminomethylcyclohexane hydrobromide, the route of step (b) according to the invention can be represented by the following formula: For example, if N-·(2 When using the sodium salt of -cyano-2-hydroxyimino-acetyl)-glycine ethyl ester and tert-butyl chloroacetate, the route of step (c) according to the invention can be represented by the following formula: For example as starting material N-( When using 2-cyano-2-methyloxy-methoxyimino-acetyl)-glycine ethyl ester and ethanolamine, the route of step (cl) according to the invention can be represented by the following formula: For example, if N-(2- When using cyano-2-methyloxy-methoxyiminoacetyl)-glycine and 4-ethoxycyclohexylamine and using N-hydroxysuccinimide as auxiliary agent, the route of step (e) according to the invention can be represented by the following formula: For example, when using as starting materials the ammonium salt of 2-cyano-2-(t-butyloxycarbonylmethoxyimino)-acetic acid, isobutyraldehyde and cyclohexylisonitrile, the route of step (f) according to the invention can be expressed as For example, in the case of 2-cyano-2-(t-butoxycarbonylmethoxyimino)-acetic acid and ethoxycarbonyl-methyl incyanate as starting materials, the route of step (g) according to the invention can be represented by the following formula: When using 2-cyano-2-(-butoxycarbonylmethoxyimino)-acetamide and bromoacetic acid diethylamide as starting materials, the process according to the invention (
The route h) can be represented by the following formula: Formula (II) gives a general definition of the 2-cyano-2-oximino-acetic esters used as starting materials when carrying out step (a) according to the invention. In this formula, R preferably has the meaning already given as suitable for this substituent in connection with the description of the substances of formula (I) according to the invention.

The 2-cyano-2-oximino-acetic acid ester of formula (I[) is unknown. However, these may be manufactured by known methods [see, for example, J.
, Antibiot. 3 7, 5 5 7 (
1984); Pesticide Science (p.
st-cide Science) 1 and 2j (I9
81) and European Patent Application Publication No. o, '2ox,
No. 999; and German patent applications no. P3,625.460, filed July 28, 1986, and German patent application no.

Formula (I) can be used in step (a) and likewise in step (b) according to the invention.
) gives a general definition of amines which are further used as starting materials in carrying out In this formula, R1 is preferably of the formula according to the invention as preferred for this substituent (
It has the meaning already given in connection with the description of the substances under I).

Amines of the formula (I [
en Chemie), Volume Xv, Parts I and 2, Georg Chime-Berlag, Stuttgart (Georg
Thieme Verbag, S tuttaga
rt) l974;', R-C-Sheppard, A Speci. A Specialist Periodical Report, Amino Acids, Peptides and Proteins
calReport.

Amino-acids, Peptides and
Proteins), The Royal Society of Chemistry, Burlington House, London.
Chemistry, Burlington Ho
use.

London) l 9 7 8, and 1. P. Greenstein and M. Winitz, Chemistry of Amino Acids
try of Amino Acids), ■. Wiley Sons Inc.,
New York, London 1961; and E. Schroder and Lübke
ubke), The Pepticise (The Pepti
cides) Volume 1, Academic Press 8 Press (Acad
emic Press), New York, London 1
965, and European Patent Application Publication No. 0.201,9
99] ; these are the object substances of an unpublished patent application by the applicant (see German Patent Application No. P3, 625,497, dated July 28, 1986); can be obtained in a generally known manner by the steps described therein.

Formula (TV) gives a general definition of the carboxylic acids used as starting materials when carrying out step (b) and step (g) according to the invention. In this formula, R preferably has the meaning already given in connection with the description of the substances of formula (I) according to the invention as suitable for this substituent.

Possible carboxyl-activated derivatives of the carboxylic acids of formula (IV) include all carboxyl-activated derivatives, such as acyl halides, such as acyl chlorides, acyl azides, as well as symmetrical and mixed anhydrides, such as mixed 0 - activation produced using an alkylcarboxylic anhydride, further activated esters such as p-nitrophenyl ester or N-hydroxysuccinimide ester, and also a binder such as dicyclohexylcarbodiimide or carbonyldiimidazole in situ; There is a carboxylic acid in an oxidized state.

Acyl chloride corresponding to the carboxylic acid of formula (■) is preferably used. These may be prepared by reacting a carboxylic acid of formula (IV) or a salt thereof with a halogenating agent such as phosphorus pentachloride, thionyl chloride or oxalyl chloride in a generally known manner.

Preference is given to using oxalyl chloride together with the sodium or potassium salt of the carboxylic acid of formula (IV).

Carboxylic acids of the formula (IV) and their carboxyl-activated derivatives are known [see, for example, Pesticide Science I2.27 (I981) and DE-A-3,521.131 in this connection; 19
German patent application No. P3,60 dated January 25, 1986
No. 2,243 and P3 dated July 25, 1986.
, 625°497].

Formula (V) gives a general definition of the 2-cyano-2-oximino-acetamide used as starting material when carrying out step (c) according to the invention.

In this formula, R1 preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent. M preferably represents hydrogen or an individual such as potassium or =6fu sodium.

2-cyano-2-oximino-acetamide of formula (V) was hitherto unknown. Some of these are unpublished patent applications filed by the applicant (see German Patent Application No. P3.702,282, January 27, 1987).
or these substances can be obtained by the method shown therein, for example, in the formula (X■) NC-CH,-〇〇-OR' (X■),
R7 represents methyl or ethyl, the cyanoacetate of 0 to
60'O1 is preferably reacted at room temperature with an amino acid derivative of the formula (I ■) NC-CH2-C○-NH-R' (X■) where R1 has the above meaning, if appropriate in the presence of a diluent such as an alcohol, and if appropriate an acid or a base such as -20 to 120°C in the presence of hydrochloric acid or alkali metal alcoholade
It can be obtained by reaction with nitrous acid or derivatives of nitrous acid at temperatures between.

Compounds of formulas (X■) and (Iff) are known; or they can be obtained by generally known methods.

The formula (VD) gives a general definition of the compounds which are additionally used as starting materials when carrying out step (C) according to the invention.

In this formula, R preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent. X preferably represents chlorine, bromine, methylsulfonyloxy or p-toluenesulfonyloxy.

The compounds of formula (Vl) are generally known compounds of organic chemistry; or they can be obtained - numerically by known methods.

Formula (■) gives a general definition of the substituted acetyl-amino acids Nisdel used as starting materials when carrying out step (d) according to the invention. In this formula, 3 and R preferably have the meanings already given in connection with the description of the substances of formula (I) according to the invention, such as those suitable for these substituents.

R5 preferably represents methyl or ethyl.

The substituted acetyl-amino acid esters of the general formula (■) are in some cases compounds according to the invention, or they may be prepared by known methods (see in this connection European Patent Application No. .201,999 and German Patent Application No. 3,521,131 and 19
German Patent Application No. P3,60 dated January 25, 1986
No. 2,243 and P3 dated July 1986, No. 288.
(See No. 625.497).

Formula (■) gives a general definition of the amines which are additionally used as starting materials when carrying out step (d) according to the invention.

In this formula, R3 and R4 preferably have the meanings already given in connection with the description of the substances of formula (I) according to the invention as suitable for these substituents.

The amines of formula (■) are generally known compounds of organic chemistry, or they can be obtained by generally known methods.

Formula (IN) gives a general definition of the acedel-amino acids used as starting materials when carrying out step (e) according to the invention. In this formula, R preferably has the meaning already given in connection with the description of the substances of formula (I) according to the invention as suitable for this substituent. Q preferably has the meaning already given in connection with the description of the substances of formula (I) according to the invention as preferred for A and B. Suitable carboxyl-activated derivatives are preferably those already mentioned as suitable in the case of the carboxylic acids of formula (IV).

In certain cases, acetyl-amino acids of the general formula ([) are compounds according to the invention or they can be prepared by known methods (in this context =71- is European Patent Application Publication No. 201..999 and German Patent Application No. 3.521,131 and German Patent Application No. 3, dated January 25, 1986,
No. 602.2/13 and No. P3,625,497 of July 28, 1986).

Formula (X) gives a general definition of the compounds which are additionally used as starting materials when carrying out step (e) according to the invention.

In this formula, Y is preferably R20- and R3R'
represents an N-group, in which R2, R3 and R4 preferably have the meanings already given in connection with the description of the substances of formula (I) according to the invention as suitable for these substituents; .

The compounds of formula (X) are generally known compounds of organic chemistry or they can be obtained by generally known methods.

Formula (XI) gives a general definition of the ammonium salt of 2-cyano-2-oximino-acetic acid used as starting material when carrying out step (f) according to the invention. In this formula, R preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent.

The ammonium salt of 2-cyano-2=ochineiminoacetic acid can be obtained by reacting the carboxylic acid of formula (IV) with ammonium in a conventional manner.

Formula (Xll) gives a general definition of aldehydes which are additionally used as starting materials when carrying out step (f) according to the invention, and formula (XIIT) gives a general definition of isonitriles. In formula (III), the R'-CH- group stands for A and B, which are preferably included in the description of the substances of formula (I) according to the invention as preferred for these substituents. has the meaning already given in connection therewith. In formula (XT[I), R4 is preferably a compound of formula (I) according to the invention as preferred for this substituent.
has the meaning given in connection with the description of the substance.

The aldehydes of formula (Xll) and the innitriles of formula (XIIT) are generally known compounds of organic chemistry, or they can be obtained by generally known methods.

Formula (XIV) gives a general definition of the incyanates used as starting materials when carrying out step (g) according to the invention. In this formula, R' preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent.

The isocyanates of formula (XIV) are generally known compounds of organic chemistry or they can be obtained by generally known methods.

Formula (XV) gives a general definition of the 2-cyano-2-oximino-acetamide used as starting material when carrying out step (h) according to the invention.

In this formula, R preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent.

The 2-cyano-2-oximino-acetamide of formula (XV) is unknown. However, these can be produced by known methods [eg Chem.

Ber, 54.1342 (I921), German Patent Application No. 2,623.847 and German Patent Application No. 2,623.847.
No. 145 and German Permanent Application No. P3,702,283, dated January 27, 987].

Furthermore, the bases used as starting materials when carrying out step (h) according to the invention include all customary inorganic and organic bases, such as in particular alkali metal alcoholides such as potassium t-
butylade; alkali metal hydroxides and carbonates such as sodium hydroxide, potassium hydroxide and potassium carbonate, and tetraalkylammonium and benzyltrialkylammonium hydroxides and alcoholades such as tetramethylammonium hydroxide and alcoholade, tetrabutylammonium hydroxide; and Alcolade or benzyltriethylammonium hydroxide and Alcolade.

Bases are generally known compounds of organic chemistry.

Formula (xvr) gives a general definition of the compounds used in addition as starting materials when carrying out step (h) according to the invention.

In this formula, R1 preferably has the meanings already given in connection with the description of the substances of formula (I) according to the invention as preferred for this substituent. X preferably represents chlorine, bromine, methylsulfonyloxy or p-toluenesulfonyloxy.

The compounds of formula (XVI) are generally known compounds of organic chemistry; or they can be obtained by generally known methods.

Possible diluents when carrying out steps (a) and (d) according to the invention are water and organic solvents. These preferably include alcohols such as methanol, ethanol or propatool; ethers such as tetrahydrofuran or 1,2-dimethoxyethane; amides such as dimethylformamide; nitriles such as acetonitrile and tertiary amines such as pyridine.

Steps (a) and (d) according to the invention are carried out, if appropriate, in the presence of a base, depending on whether the particular amine is used in the form of an acid addition salt. Suitable in this case are the customary organic and inorganic bases. Preferably tertiary amines such as triethylamine; alcoholades such as sodium methylate and alkali metal carbonates such as potassium carbonate may be mentioned.

When carrying out steps (a) and (d) according to the invention, the temperature can be varied within a relatively wide range. Generally, this process takes about 120
It is carried out at a temperature between °C and reflux temperature, preferably at room temperature.

When carrying out steps (a) and (d) according to the invention, all reactants can be used in excess; it is preferred to use equimolar amounts. The reaction is carried out and the reaction product of formula (I) is worked up and generally isolated in conventional manner.

Possible diluents for steps (b) and (e) according to the invention are inert organic solvents. These include ketones such as acetone or methyl ethyl ketone; esters such as ethyl acetate or methyl acetate; amides such as dimethylformamide; nitriles such as acetonitrile; chlorinated hydrocarbons such as methylene chloride or carbon tetrachloride; hydrocarbons such as toluene; or ethers such as Tetrahydrofuran; or mixtures thereof.

Possible acid binders for steps (I) and (e) according to the invention are the customary inorganic and organic acid binders. These preferably include tertiary amines such as triethylamine, pyridine or N-methylmorpholinol, and inorganic bases such as sodium carbonate or calcium carbonate.

Steps (b) and (e) according to the invention are carried out, if appropriate, in the presence of a catalyst. Examples which may be mentioned are 4-dimethyl-aminopyridine, 1-hydroxybenthriazole or dimethylformamide.

When carrying out steps (b) and (e), the temperature can be varied within a relatively wide range. Generally, this process is carried out at -60 to 120°
C, preferably at a temperature of -20 to 40°C.

When carrying out steps (I) and (e) according to the invention, equimolar amounts are preferably used. The reaction is carried out and the reaction product of formula (I) is worked up and isolated in generally conventional manner.

Possible diluents for the process according to the invention (c) are organic solvents. These include alcohols, such as methanol and ethanol; ketones, such as acetone and methyl isobutyl ketone; included.

Possible bases for step (c) according to the invention include all customary organic and inorganic bases. These preferably include tertiary amines such as triethylamine, pyridine and 1,8-diazabicyclo[5.4.01-undes-7
DBU, as well as inorganic bases such as sodium carbonate, potassium carbonate or carbonate.

When carrying out step (c) according to the invention, the reaction temperature can be varied within a relatively wide range. Generally, this process is performed from O to 150
It is carried out at a temperature between 20 and 120°C, preferably between 20 and 120°C.

When carrying out step (c) according to the invention, 1 per mole of 2-cyano-2-oximino-acetamide of formula (V)
~3 mol, preferably 1 to 2 mol of a compound of formula (W) is generally used. The reaction is carried out and the reaction product of formula (I) is worked up and isolated in generally conventional manner. Formula (V)
It should be emphasized that the 2-cyano-2-oximino-acetamide can be further reacted directly after its preparation without isolation.

Possible diluents for step (f) according to the invention are all customary organic solvents. These preferably include alcohols such as methanol or ethanol; ethers such as diethyl ether; chlorinated hydrocarbons such as chloroform or carbon tetrachloride; and ketones such as acetone.

When carrying out step (f) according to the invention, the temperature can be varied within a relatively wide range. Generally, the temperature is -20 to 40°C
1 Preferably carried out at a temperature of 0 to 20'O.

When carrying out step (f) according to the invention, equimolar amounts are preferably used. carrying out a reaction and treating the reaction product of formula (I);
and generally isolated by conventional methods.

Possible diluents for step (g) according to the invention are inert organic solvents. These include aromatic hydrocarbons such as toluene; chlorinated hydrocarbons such as methylene chloride; ethers such as tetrahydrofuran or 1,2-dimethoxyethane; esters such as ethyl acetate; and nitrites such as acenitrile.

Step (g) according to the invention is carried out if appropriate in the presence of a catalyst. Examples that may be mentioned are triethylamine, ], ]4-diazabicyclo2,2.2]octane (DABCO) and 1,8-diazabicyclo[5.

4, 0] - Undesuwaen (DBU).

When carrying out step (g) according to the invention, the temperature can be varied within a relatively wide range. Generally, the reaction is carried out at a temperature between -20°C and reflux temperature, preferably at room temperature.

When carrying out step (g) according to the invention, all reactants can be used in slight excess and it is preferred to use 18 molar amounts. The reaction is carried out and the reaction product of formula (I) according to the invention is worked up and isolated in generally customary manner.

Possible diluents for step (h) according to the invention are inert organic solvents. Ethers such as diethyl ether/L-, diisopropyl ether, tetrahydrofuran or dioxane; ketones such as acetone or methyl ethyl ketone; furthermore acetonitrile and dimethylformamide may be suitably used.

When carrying out step (h) according to the invention, the reaction temperature can be varied within a relatively wide range. Ring formation generally ranges from 0 to 100°
It is carried out at a temperature between 0 and 30°C, preferably between 0 and 30°C. The subsequent alkylation is generally carried out at temperatures between 0 and 150°C, preferably between 60 and 120°C.

When carrying out step (h) according to the invention, preferably equimolar amounts, if appropriate up to a 1 molar excess of the alkylating agent of formula (XVI) are used. Although the salt of the compound of formula (XV) can be isolated if necessary, this step can be carried out without isolation. In some cases it may be advantageous to first convert the acetamide of formula (X I found out that it is. The reaction is carried out and the reaction product of formula (I) is worked up and - isolated in a numerically customary manner.

The compounds according to the invention have a strong microbicidal action (micro-o
bicidal action) and can be used in practice in controlling undesirable microorganisms.

The active compounds are suitable for use as toxic biological agents, in particular fungicides.

For example, a fungicidal and fungicidal agent for plant protection is Plasmodiophoromycetes (Plasmodiophoromycetes).
es), Oomycetes, Chy-tridiomycetes, Zygomycetes, Cysticomycetes (A s)
comycetes), Basidiomycetes
y-cetes), and Deuteromycota (Deutera
omycetes).

Some causative organisms for the fungal and fungal diseases shown under the above ash conditions are listed below as non-limiting examples: PyLhium
A species example is seedling damping-off (Pythium ultimum).
; Phytophthora species such as Phytophthora jnfssta;
ns); Busoidoperonospora (P5eudoper
onospora) species such as downy mildew (Pse-udop
eronosporahumuli Mapukoha Pseud
operonosp-ora cubensis);
Plasmopara species such as P lasmopara viticola;
Peronospora species such as downy mildew (Peronosporapisi or P.
brassicae) ; Erysihue (Erysi-
phe) species such as powdery mildew (E rysiphe)
graminis); Sphaerotheca (Sphaero
theca) species such as powdery mildew (Sphaeroth
eca fuliginea); Podos 7 gills (P
odosphaera) species such as powdery mildew (P od
ospha-era 1eucotricha);
Venturia species such as V.
enturia 1naqualis); Pyrenophora species such as P. enturia 1naequalis);
yrenophorateres or P, gr
aminea) ; (conidiophore-shaped: D rechs
lera, synonym: Helminthosporium
) ; Cochliobolus species such as Coch-1iobolus 5at
ivus) (conidioform: D rechslera.

Synonyms: Helminthosporium; Uromyces species e.g.
omyces appendiculat-us)
;Puccinia species such as Fuccinia recondita;
; Tilletia species such as T 1lletiacaries ; U st i Iago species such as Ustilago nuda or Ustilag;
o avenae); Pellic
ularia) species such as Pellicular
ia 5asakii); Piricularia (Pyr
icularia) species such as rice blast (Pyricu
lariaoryzae) ; Fusalium (F us
sarium) species such as Fusarium curmorum (F
ussarjum culmorum); Botrytis species such as botrytis (B.
otrytis cinerea); Septoria (3
6ptoria) species, such as Septoria blight (Septoria
a nodorum) ; Leptosphaeria (L e
ptosphaeria) species such as Leptosphaeria nod.
orum); Cercospora (CercosplJra)
Species such as Cercospora canescens
ra canascens); Alternaria (A
Itternaria) species such as black spot (A Ittern)
ariabrass 1cae) and Pseudocercosporel I
a) Species such as P. lycoides (P. eudocercosporel Ia)
herpotrichoides).

The good tolerability of the active compounds by plants at the concentrations required for controlling plant diseases makes it possible to treat the above-ground parts of plants, the growing stems and seeds, and the soil.

As pest control agents, the active compounds according to the invention can be used as pest control agents against Phytophthora on tomatoes.
) species such as P phytophtborainfe
and can also be successfully used in controlling P Iasmopara species such as downy mildew (P lasmopara viticola) on grapes.

The active compounds according to the invention not only exhibit a protective effect;
It should be particularly emphasized that the active effect is present upon application after contamination with fungal spores.

Furthermore, the active compounds according to the invention are very highly suitable for combating Pyricularia species such as Pyricularia oryzae on rice.

The active compounds can be used in conventional compositions such as solutions, emulsions, suspensions, powders, capsules, liniments, aerosols, natural and synthetic substances impregnated with the active compound, polymeric substances for seeds, etc. Can be converted into fine capsule and coating compositions, as well as U L V cold and warm mist compositions.

These compositions are prepared in known manner, for example, by mixing the active compounds with extenders, i.e. liquid solvents and/or solid carriers, and optionally surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. Ru. Furthermore, when water is used as an extender, an organic solvent can also be used, for example, as an auxiliary solvent.

As liquid solvents, mainly aromatic hydrocarbons such as pysylenes, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroegulene or methylene chloride,
Aliphatic hydrocarbons such as cyclohexane, or paraffins such as mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,
Strong polar solvents such as dimethylformamide and dimethylsulfoxide and water are suitable; by liquefied gaseous extenders or carriers we mean liquids that are gaseous at normal temperature and pressure, such as halogenated hydrocarbons and Aerosol propellant bases such as butane, propane, nitrogen and carbon dioxide; solid carriers such as ground natural minerals such as kaolin, clay, talc, quartz,
Attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly dispersed silicic acid, alumina and silicates are suitable; as solid carriers for the granules, ground and fractionated natural rocks, such as calcite. , marble, pumice, sepiolite and dolomite as well as inorganic and organic ground synthetic granules and granules of organic substances such as sawdust, coconut, corn cobs and tobacco stalks; emulsifiers and/or foaming Agents include nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfonyl esters, arylsulfonyl ethers, Also suitable are albumin hydrolysis products; suitable dispersants are, for example, lignin sulfite waste liquor and methylcellulose.

Examples of adhesives include carboxymethylcellulose and powder.
Particulate or latex natural and synthetic polymers such as gum arabic, polyhinyl alcohol and polyhinyl acetate-1-, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids can be used in the composition. Further additives can be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes and metal phthalocyanine dyes, and trace nutrients such as iron, manganese, boron, copper, cobal I, molybdenum and Salts of zinc can be used.

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

The active compounds according to the invention may also be combined with other known active compounds, such as fungicides, bactericides, etc.
ide), insecticides, acaricides, nematicides
cide), herbicides, bird repellants, growth factors, plant nutrients and soil structure improvers or in various forms of use.

The active compounds can be used as such or in the form of preparations or further diluted use forms, such as ready solutions, emulsions, suspensions, powders, coatings and granules. can.

These forms can be prepared in the usual manner, such as by dispersing, dipping, spraying, atomizing, etc.
ing), misting, vaporization (
vaporising), pouring, forming a 5-lurry, brushing, dusting, granulating, dry smearing, semi-wet smearing, wet smearing, slurry smearing or ink-crusting (enc-r
applying).

When treating plant parts, the active compound concentration in the application forms can be varied within a substantial range. Generally the concentration is between 1 and 0.0001% by weight, preferably between 5 and 0.001% by weight.

When treating seeds, generally 0.00
1-50g, preferably 0. Requires O1-lh active compounds.

When treating soil, it is generally
An active compound concentration of ~0.1% by weight, preferably 0001-0.02% by weight is required.

Example I H30 Il (Step C) N-[(E)-2-cyano-2-hydroxyimino-acetylcoglycine ethyl ester sodium salt 11
y (0.05 mol), dimethylformamide 50m
12 and t-butyl chloroacetate 8°3g (0,055
mol) mixture was stirred at room temperature for 15 hours. After distilling off the solvent in vacuo, the residue was dissolved in 150 ml of ethyl acetate. The solution was washed with water (3 x 50 ml), dried and evaporated.

The crude product was filtered over 100 g of silica gel.

10.2 g (65% of theory) of N-[(E)-2-(t-butoxycarbonylmethoxyimino)-2-cyano-acetylcoglycine ethyl ester were obtained as a yellow oil.

NMR (CDC13) δ: 1.3 (t, 3H), 1.
5 (s.

9H), 4.13 (d, 2H), 4.24 (q, 2
H), 4.84Cs, 2H), 7.1(t, NH).

. A sodium salt tirade solution prepared from 1.2 g (0.05 mol) of sodium and 20 m4 of absolute ethanol was diluted with 88% N-cyanoacetyl-glycine ethyl ester9.
．． 0g (0.05 mol), isoamine nitrite 5.9g
(0.05 mol) and ethanol (anhydrous) 20 ml
was added dropwise to the mixture at 0°C and the mixture was stirred at room temperature for 15 hours. Evaporate the solution and add ether 2
0 ml (l) was added to the residue, the precipitate was filtered off with suction and dried in a vacuum desiccator.

11 g (99% of theory) of the sodium salt of +1-[(E)-2-cyano-2-hydroxyimino-acetyl 1-glycine ethyl ester were obtained as a highly hygroscopic solid.

Solution of 26% sodium methylate in methanol 6
30 g (3 mol) was added to Improper Tool 750 m0. In a solution of 297 g (3 mol) of methyl cyanoacetate and 420 g (3 mol) of glycine ethyl ester hydrochloride in
It was added at 0° C. and the mixture was stirred at room temperature for 15 hours.

After distilling off the solvent, the residue was poured into 200ml of water. and methylene chloride 750m0. The aqueous phase was mixed with methylene chloride (
2X]OOmf2), the combined organic phases were dried and evaporated. The crude product was dissolved in ether 500m
It was crystallized from ff.

350 g (60% of theory) of N-cyanoacetylglycine ethyl ester having a melting point of 95-97°C were obtained;
Content: 88% (gas chromatography).

The following (2-cyano-2-oxyiminoacetyl)-amino acid derivatives of general formula (I) were obtained analogously and by steps (a) to (h) according to the invention: Use example (B) (C ) H 0OCH3 (D) 99-Example A Phytophthora test (tomato)/
Active solvent: 4.7 parts by weight of acetone Emulsifier: 0.0 parts by weight of alkylaryl polyglycol ether.
To prepare a suitable preparation of 3 parts by weight of active compound, 1 part by weight of active compound is mixed with the above amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test starting activity, young plants were infected with late blight (P hy
tophthora 1nfestans). Plants were placed in a culture chamber for 7 hours at approximately 20°C and 100% relative humidity. After a short drying period, the plants were sprayed with the active compound preparation until dripping wet.

Plants were placed in a culture chamber at 100% relative humidity and approximately 20°C.

Evaluation was performed 38 days after inoculation.

In this test, the compounds according to Preparation Examples 4.6.8.9.11.12 and 13, for example, showed clearly superior activity compared to those in the field. The results are shown in Table A below.

Example B Downy mildew (PIasmopara) test (grapes)/Protection solvent: 4.7 parts by weight of acetone Emulsifier: Alkylaryl polyglycol ether 0.
To prepare a suitable preparation of 3 parts by weight of active compound, 1 part by weight of active compound is mixed with the above amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.

To test the protective activity, young plants were sprayed with the active compound preparation until dripping wet. After the spray coating has dried, the plants will develop mildew (PIasmo).
para viticola) and then placed in a thermostatic chamber at 20-22° C. and 100% relative humidity.

The plants were then placed in a greenhouse for 5 days at 22°C and 80% humidity. The plants were then moistened and placed in a constant humidity chamber for one day.

Evaluation was performed 7 days after inoculation.

In this test, the compound according to Preparation Example 11, for example, showed clearly superior activity compared to those in the field. The results are shown in Table 8 below.

No. A Blue Phytophthora test (tomato)/activity (Publicly known) (B) (Publicly known) (C) H3 CH40 II CH30 ]11 Nl+ 0OCR3 (Publicly known) (D) CH30 The main features and aspects of the invention are as follows.

1, -Formula (I) where R1 is a group -A-COO, R2 or -B-CON
R3R' represents, A represents a linear or branched alkylene chain which may be optionally substituted, B represents a linear or branched alkylene chain which may be optionally substituted, R2 substituents are halogen, hydroxyl, alkoxy,
acyloxy, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocycle; or R2 represents optionally substituted cycloalkyl or optionally substituted R3 represents hydrogen; or a substituent halogen, cyano, -COOR', -CONR R1, -NR" Rm
, -OR", -3(0), R", acyl and optionally substituted alkyl with optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl in each case : or R3 further represents in each case optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocycle; R4 represents hydrogen or a substituent halogen, cyano, -COOR' , -CONR"R", -NRr'R
", -OR", -3(0), R", 7'yl, and in each case optionally substituted aryl, heterocycle,
cycloalkyl and cycloalkenyl; or R4 is further optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or the group -OR in each case; ”, or A and R2 together with the atoms bonded to the nucleus crystal represent an optionally substituted ring, or B and R3 together with the atoms bonded to the nucleus crystal represent a ring that may be optionally substituted. represents an optionally substituted ring, or R3 and R4 together with the nitrogen atom bonded to the nucleus represent an optionally substituted heterocyclic group which may further contain a heteroatom. , R is a substituent halogen, -COOR', -CONRI
I RI I +, -〇R1v1 represents a substituted alkyl having an optionally substituted heterocycle other than acyl and azolyl; or R represents an optionally substituted cycloalkenyl; represents hydrogen or the substituent halogen and optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl in each case, RII and RIv are the same or different, and Hydrogen or substituent halogen, -C
OORN, -CONR'R'' and in each case optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl; or RII and R1 also represent alkenyl, alkynyl or represents an optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocycle in each case or optionally substituted which together with the nitrogen atom bonded to the nucleus may further contain a heteroatom; (2-cyano-2-oxyiminoacetyl)-amino acid derivatives of (2-cyano-2-oxyiminoacetyl)-amino acid derivatives, and RN represents hydrogen, alkyl, aralkyl or acyl, and n represents a number of 0, ■ or 2; Its steric and optical isomers and isomer mixtures.

2, Formula (I) 4mT, R1 represents a group -A-COOR" or -B-CONR3R', and A is a carbon atom 1 to
represents a straight-chain or branched alkylene having 4 carbon atoms, B represents a straight-chain or branched alkylene having 1 to 4 carbon atoms, and R2 has 1 to 6 carbon atoms. Represents an optionally substituted straight-chain or branched-chain alkyl; substituents that may be mentioned include halogen and optionally halogen, in each case containing 1 carbon atom.
phenyl and cycloalkyl having 3 to 6 carbon atoms optionally substituted with 1 to 5 identical or different substituents from the group consisting of alkyl having ~4 and alkoxy; or represents cycloalkyl preferably having 3 to 6 carbon atoms and optionally substituted with 1 to 5 identical or different alkyl substituents having 1 to 4 carbon atoms; represents cycloalkenyl having ~7 atoms and optionally substituted with 1 to 5 identical or different alkyl substituents having 1 to 4 carbon atoms, R3 further represents hydrogen or It represents a straight-chain or branched alkyl having 1 to 4 atoms and optionally substituted with 1 or 2 substituents, and the substituents that may be mentioned include halogen, cyano, -COOR',
-CONR"R", -NR"R", -OR"
, -5(0).

RN1 Acyl having 2 to 9 carbon atoms, phenyl optionally substituted with 1 to 5 identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms, 1 heteroatom -3 and optionally substituted with 1 to 5 identical or different substituents from the group consisting of halogen and alkyl and alkoxy having in each case 1 to 4 carbon atoms 6-membered heterocyclic radicals as well as cycloalkyl having 3 to 6 carbon atoms, optionally substituted with 1 to 5 identical or different alkyl substituents having 1 to 4 carbon atoms in each case; and cycloalkenyl having 5 to 7 carbon atoms; or R3 further represents in each case straight-chain or branched alkenyl or alkynyl having 2 to 6 carbon atoms: 5 carbon atoms ~
cycloalkenyl having 7 -1,11- atoms and optionally substituted with 1 to 5 identical or different alkyl substituents having 1 to 4 carbon atoms; represents a cycloalkyl group having 1 to 4 carbon atoms, which may optionally be substituted with 1 to 5 identical or different substituents, in which case substituents that may be mentioned include halogen, in each case 1 to 4 carbon atoms; alkyl and alkoxy, cyano, amino, carbamoyl, alkylamino, dialkylamino, alkylcarbamoyl and dialkylcarbamoyl having in each case 1 to 4 carbon atoms in each alkyl moiety, 1 to 4 carbon atoms in the alkoxy moiety; alkoxycarbonylamino, cycloalkyl and cycloalkylalkyl having 5 or 6 carbon atoms in the cycloalkyl moiety and 1 to 4 carbon atoms in the linear or branched alkyl moiety, and optionally halogen and 1 carbon atom phenyl and pyrrolidone optionally substituted with 1 to 5 identical or different substituents from the group consisting of alkyl having ~4; or R3 optionally further contains halogen, in each case 1 to 4 carbon atoms; Alkyl and alkoxy having 4 and in each case l carbon atoms
or 2 and 1 same or different halogen atom
1 to 5 identical or different substituents from the group consisting of halogenoalkyl and halogenoalkoxy having ~5
5 or 6 phenyl optionally substituted with 5 or 6, having 1 to 3 heteroatoms, the same or different, and optionally substituted with 1 to 5 the same or different substituents; represents a membered heterocyclic group, and substituents that may be mentioned include halogen, mercapto, phenyl, as well as straight-chain or branched alkyl having 1 to 4 carbon atoms per alkyl moiety, alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl, in which R4 has the meaning R3 or represents a polycyclic carbocyclic group or the group -OR'', or A and R2 together with the atoms bonded to the nucleus represents a ring of the formula, where 21 represents a linear or branched alkylene chain having 1 to 4 carbon atoms, or B
and R3 together with the atoms bonded to the nucleus crystal represent a ring of the formula, where 72 represents a linear or branched alkylene chain having 1 to 4 carbon atoms, and 23 represents hydrogen or represents alkyl having 1 to 4 carbon atoms, or R3 and R4 together with the nitrogen atom bonded to the nucleus have 1 to 3 other identical or different heteroatoms, and optionally the same or [optionally substituted with 1 to 5 different substituents] represents a bi- or tricyclic heterocyclic group or a spiro-heterocyclic group, in which the substituents that may be mentioned include in each case a carbon Straight-chain or branched alkyl or alkoxy having 1 to 4 atoms, cycloalkyl, hydroxyl and oxo groups having 3 to 6 carbon atoms, straight-chain or branched having 2 to 4 carbon atoms chain alkenyl, hydroxycarbonyl, alkoxycarbonyl carbamoyl having 1 to 4 carbon atoms in the straight or branched alkyl moiety, in each case 1 to 4 carbon atoms in each alkyl moiety; alkyl- and dialkylcarbamoyl and in each case optionally /10 g and identical or different substitutions from the group consisting of straight-chain or branched alkyl and alkoxy having from 1 to 4 carbon atoms in each case phenyl optionally substituted with 1 or 2 groups and phenylalkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, and R having 1 to 6 carbon atoms; , and represents a linear or branched alkyl substituted with one or two substituents, and examples of the substituents that may be mentioned include -COOR', -COOR',
-CONR"R"', ORI V.

Other than acyl having 2 to 9 carbon atoms and azoyl, the same or different substituents 1 to 3 are from the group consisting of 1 to 3 heteroatoms and optionally halogen and alkyl having 1 to 4 carbon atoms. a 3- to 6-membered heterocycle optionally substituted with 5; or a group in which R is more preferably alkyl having 5 to 7 carbon atoms and optionally having 1 to 4 carbon atoms; represents a cycloalkenyl optionally substituted with 1 to 5 of the same or different substituents from , R1 represents hydrogen or a straight-chain or branched alkyl having 1 to 6 carbon atoms, R1
are hydrogen, straight-chain or branched alkyl having 1 to 6 carbon atoms, having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, and are the same or different as appropriate phenylalkyl optionally substituted with 1 to 5 substituents, possible substituents being halogen, alkyl and alkoxy having in each case 1 to 4 carbon atoms and in each case carbon There are halogenoalkyl and halogenoalkoxy having 1 or 2 atoms and 2 to 5 identical or different halogone atoms; or R1+ in each case further contains 1 to 4 carbon atoms in each alkyl moiety. alkoxycarbonylalkyl, carbaniylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having from 3 to 6 carbon atoms and optionally straight or branched chain alkyl having from 1 to 4 carbon atoms; represents a cycloalkyl optionally substituted with , R1 is hydrogen, a straight-chain or branched alkyl having 1 to 6 carbon atoms, or a straight-chain or branched alkyl moiety having a carbon atom represents phenylalkyl having 1 to 4 substituents and optionally substituted with 1 to 5 of the same or different substituents, in which case the possible substituents on phenyl include those listed for R1+ If there are substituents on phenyl, RI [I further represents in each case alkoxycarbonylalkyl, carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having from 1 to 4 carbon atoms in each alkyl moiety, or represents cycloalkyl having 3 to 6 atoms and optionally substituted with a straight-chain or branched alkyl having 1 to 4 carbon atoms; R1111 is hydrogen, carbon atoms 1 to 6 straight-chain or branched alkyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, and optionally substituted with 1 to 5 of the same or different substituents represents phenylalkyl which may be substituted, in which case the possible substituents on phenyl include the substituents on phenyl listed for R11: or RKI further contains 2 to 2 carbon atoms.
(2-Cyano-2-oxyiminoacetyl)-amino acid derivatives of the formula (I) according to 1 above, representing acyl having 9 atoms, and n representing the number 0, l or 2, and their geometry and optics. Isomer mixture.

3. In formula (I), R1 is a group -A-G.

represents OR2 or -B-CONR3R', and A is a group -
CH2-1-CH(CH3)- or -CH2CH2-
, B represents a group -CH2-1-CH(CH3)- or -CH2CH2-, R2 represents a straight-chain or branched alkyl having 1 to 4 carbon atoms,
R3 represents hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms and optionally being substituted with 1 or 2 identical or different substituents; Substituents that can be mentioned include halogen,
Cyano, -COOR', -CONRTIRI'[, -
NRIIRII+, -0RIII, -5(0). RN,
phenyl having 2 to 9 carbon atoms optionally substituted with 1 to 3 identical or different substituents from the group consisting of halogen and alkyl having 1 to 4 carbon atoms; 1 to 3 identical or different substituents from the group consisting of 1 to 3 heteroatoms and optionally halogen and straight-chain or branched alkyl and alkoxy having in each case 1 to 4 carbon atoms; 5- or 6-membered heterocyclic radicals optionally substituted with 3 and optionally substituted with straight-chain or branched alkyl having 1 to 4 carbon atoms in each case cycloalkyl having 3 to 6 carbon atoms and cycloalkenyl having 5 to 7 carbon atoms; or R3 is also a straight-chain or branched cycloalkyl having in each case 2 to 6 carbon atoms; represents alkenyl or alkynyl or optionally substituted cycloalkyl having 3 to 6 carbon atoms; possible substituents include halogen; in each case straight chain having 1 to 4 carbon atoms; straight-chain or branched alkyl and alkoxy, cyano, amino, carbamoyl, in each case straight-chain or branched alkylamino having from 1 to 4 carbon atoms in each alkyl moiety; dialkylamino, alkylcarbamoyl and dialkylcarbamoyl, alkoxycarbonylamino having 1 to 4 carbon atoms in the straight-chain or branched alkoxy moiety, in each case 5 or 6 carbon atoms in the cycloalkyl moiety and straight-chain cycloalkyl and cycloalkylalkyl having 1 to 4 carbon atoms in the alkyl moiety in the form of a chain or branched chain, and optionally halokene and 1 to 4 carbon atoms;
phenyl and pyrrolidone optionally substituted with 1 to 3 identical or different substituents from the group consisting of alkyl having: or R3 optionally further contains halogen, in each case 1 to 4 carbon atoms; straight-chain or branched alkyl and alkoxy having in each case 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms from the group consisting of represents phenyl, optionally substituted with 1 to 3 different substituents, or has 1 to 3 heteroatoms, and optionally substituted with 1 to 3 of the same or different substituents; It represents a 5- or 6-membered heterocyclic group, in which substituents which may be mentioned for the heterocyclic group include halogen, mercapto, phenyl and linear groups having 1 to 4 carbon atoms per alkyl group. or branched alkyl, alkoxy, alkylthio, alkylsulfinyl and alkylsulfonyl: R'' further has the meaning R3, or represents a polycyclic carbocyclic group or the group -OR, or A and R2 together with the atoms bonded to the core crystal represent a 5- or 6-membered ring of the formula optionally substituted with alkyl having 1 to 4 carbon atoms, or B and R3 bond to the core crystal. represents a 5- to 7-membered ring of the formula optionally substituted with alkyl having 1 to 4 carbon atoms, or R3 and R4 together with the nitrogen atom bonded to the nucleus represents a 1.2- or 3-cyclic heterocyclic or spiro-heterocyclic group which may be optionally substituted with 1 to 5 identical or different substituents; are oxazolidine, pyrrolidine, imidazolidine, piperidine, piperazine, morpholine, thiomorpholine, 1,3-oxazane and J,3-diazan; these heterocyclic radicals can in each case optionally contain one or two benzenes or cyclohexane. can be fused to a ring or optionally bridged with methylene or ethylene;
Substituents which may be mentioned for all heterosystems include in each case straight-chain or branched alkyl or alkoxy having 1 to 4 carbon atoms, 3 to 6 carbon atoms;
Cycloalkyl, hydroxyl and oxo groups having 2 to 4 carbon atoms, straight-chain or branched alkenyl having 2 to 4 carbon atoms, hydroxycarbonyl, 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety alkoxycarbonyl, carbamoyl, alkyl- and dialkylcarbamoyl having in each case 1 to 4 carbon atoms in each alkyl moiety and in each case halogen and straight chain having in each case 1 to 4 carbon atoms phenyl which may be substituted with one or two identical or different substituents from the group consisting of straight-chain or branched alkyl and alkoxy; and 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety; phenylalkyl having 1 to 4 carbon atoms, and R represents a substituted straight-chain or branched alkyl having 1 to 4 carbon atoms, examples of suitable substituents which may be mentioned include halogen, - COOR
' , -CONR"RIl, -C)R", 2 to carbon atoms
9 acyl and optionally substituted with 1 to 3 identical or different alkyl substituents having 1 or 2 carbon atoms, or R is optionally further substituted with methyl represents cyclohexenyl or cyclopentenyl optionally substituted with 1 to 3 groups, R1 represents a linear or branched alkyl having 1 to 4 carbon atoms, Rn represents hydrogen, represents straight-chain or branched alkyl having 1 to 4 atoms or benzyl or phenethyl, which in each case may optionally be substituted with 1 to 3 identical or different substituents; Among the substituents on phenyl that may be mentioned are fluorine, chlorine, methyl, methoxy and trifluoromethyl; or in each case alkoxycarbonylalkyl or dialkylcarbamoylalkyl having 1 or 2 carbon atoms in each alkyl moiety; represents cycloalkyl having 3 to 6 atoms and optionally substituted with 1 to 3 identical or different substituents from the group consisting of methyl and ethyl, RIl has the meaning of R1; RN is hydrogen,
represents straight-chain or branched alkyl having 1 to 4 carbon atoms or benzyl or phenethyl, which in each case may optionally be substituted with 1 to 3 identical or different substituents; Substituents on phenyl that may be mentioned include fluorine, chlorine, methyl, methoxy and trifluoromethyl; or RN further represents acyl having 2 to 9 carbon atoms and n is the number O, l or 2. (2-cyano-
2-oxyiminoacetyl)-amino acid derivatives and their geometric and optical isomers and isomer mixtures.

4, -In formula (I), R1 is a group -B-C0-NR
3R', B is a group -CH2-1-CH(CH3)
- or -CH2CH2-, R3 represents hydrogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms, and R4 represents hydrogen or a straight-chain or branched alkyl having 1 to 4 carbon atoms; represents a branched alkyl, R
represents substituted alkyl having 1 or 2 carbon atoms, and possible substituents include halogen, alkylcarbonyl having 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, Group -COOR', -CO
NRIIRnl and -ORN and a heterocyclic group of the formula; or R represents 1-cyclohexenyl optionally further substituted with 1 to 3 methyl substituents;
1 represents methyl, ethyl, n- or 1-propyl or n-1l-1sec- or t-butyl, R
Tl and Ro are the same or different, and represent hydrogen, methyl, ethino-, n- or ]-propyl, or are optionally substituted with 1 to 3 of the same or different substituents having chlorine and methyl as substituents; or alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, or alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, respectively -] represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl, or represents cyclohexyl, optionally substituted with 1 to 3 methyl substituents, and R is hydrogen, alkyl having 1 or 2 carbon atoms or represents benzyl, optionally substituted with 1 to 3 identical or different substituents, the substituents on phenyl which may be mentioned in this case being fluorine, chlorine and methyl; ) (2-cyano-2-oxyiminoacetyl)-amino acid derivatives and their geometric and optical isomers and isomer mixtures.

5. In formula (I), R1 is a group -B-CO-NR3R
', B represents a group -CH2-1-CHCCH3)- or -CH2CH2-, R3 is hydrogen, a linear or branched alkyl having 1 to 4 carbon atoms or 1 to 3 carbon atoms and substituent 1 or 2
represents an alkyl substituted with Identical or different substituents 1 from the group consisting of alkylcarbonyl having 1 to 4 carbon atoms in the branched alkyl moiety, alkoxy and alkylthio having in each case 1 or 2 carbon atoms, and optionally chlorine and methyl. Phenyl, 2-furyl, 2-pyridyl, optionally substituted with ~3, ■
-morpholino, cyclopropyl and cyclohexyl: or R3 further represents allyl or propargyl, ■-cyclohexenyl or cyclohexyl substituted with 1 to 3 identical or different substituents; Substituents which may be mentioned in this case include chlorine, methyl, ethyl, methoxy, cyano, amino, in each case alkyl- and dialkylamino having 1 or 2 carbon atoms in each alkyl moiety, carbamoyl, in each case 1 or 2 carbon atoms in each alkyl moiety
alkyl- and dialkylcarbamoyl, cyclohexyl, cyclohexylalkyl having 1 or 2 carbon atoms in the alkyl moiety, and 1-pyrrolidin-2-one; or also from the group where R3 optionally consists of chlorine and methyl; The same or different substituents 1-
represents phenyl optionally substituted with 3 or 2-pyridyl or 2-pyrimidinyl optionally substituted in each case with 1 to 3 methyl substituents;
represents 2-benzothiazolyl, optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine, methyl and methoxy, or represents 1.2.4-triazol-3-yl; 1,2,4-thiadiazol-5-yl, optionally substituted by phenyl, optionally mercapto, straight-chain or branched alkyl having 1 to 4 carbon atoms and in each case optionally substituted with 1 to 3 identical or different substituents from the group consisting of alkylthio, alkylsulfinyl and alkylsulfonyl, in each case linear or branched, having 1 to 4 carbon atoms; , 3.4-thiadiazol-5-yl or a radical. 2 and R6 represents alkyl having 1 to 3 carbon atoms and substituted with 1 or 2 substituents, and examples of substituents that may be mentioned include chlorine, hydroxyl, linear or branched alkylcarbonyloxy having 1 to 4 carbon atoms in the chain alkyl moiety; alkylcarbonyloxy having 1 to 4 carbon atoms in the straight chain or branched alkyl moiety; in each case 1 or the same or different substituents from the group consisting of alkoxy and alkylthio having 2 and optionally chlorine and methyl;
Phenyl optionally substituted with 3, 2-furyl, 2
-pyridyl, 1-morpholino, cyclopropyl and cyclohexyl: or R4 further represents allyl or propargyl, or 1-cyclohexenyl, or cyclosubstituted with 1 to 3 identical or different substituents; -]3+- Hexyl, and possible substituents include chlorine,
methyl, ethyl, methoxy, cyano, amino, alkyl- and dialkylamino, carbamoyl, in each case with 1 or 2 carbon atoms in each alkyl moiety;
alkyl- and dialkylcarbamoyls having in each case 1 or 2 carbon atoms in each alkyl moiety;
cyclohexyl, 1 or 2 carbon atoms in the alkyl moiety
or cyclohexylalkyl and l-pyrrolidin-2-one having the same or different substituents 1 to
represents phenyl optionally substituted with 3 or 2-pyridyl or 2-pyrimidinyl optionally substituted in each case with 1 to 3 methyl substituents;
2-thiazolyl optionally substituted with phenyl or 2-benzothiazolyl optionally substituted with 1 to 3 identical or different substituents from the group consisting of chlorine, methyl and methoxy , 1, 2.
4-1-Riazol-3-yl or optionally substituted with phenyl, 2゜4-thiadiazol-5
-yl or optionally mercapto, straight-chain or branched alkyl having 1 to 4 carbon atoms and in each case straight-chain or branched alkyl having 1 to 4 carbon atoms; represents a chain alkylthio, alkylsulfinyl and alkylsulfonyl, or represents a group or R4 is in addition identical or different substitutions from the group consisting of hydroxyl, alkoxy having 1 or 2 carbon atoms, optionally chlorine and methyl; represents benzyloxy optionally substituted with 1 to 3 groups, or represents l-adamantyl, 2-norbornyl, - or 2-decalyl or 1- or 2-tetralyl; R is l or 2 carbon atoms; represents a substituted alkyl having 1 to 4 carbon atoms, and substituents which may be mentioned include halogen, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, the radicals -COR', -C0NRIIRII' and RN and the formula or R represents 1-cyclohexenyl, optionally substituted in each case with 1 to 3 methyl substituents, and R1 is methyl, ethyl, n-
or represents 1-propyl, n-1l-1sec- or t-butyl, Rn and R1 are the same or different, and hydrogen, methinoethyl, n-
or 1-propyl or identical or different substituents 1 to 1 with optionally chlorine and methyl as substituents;
represents benzyl optionally substituted with 3 or alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, or in each case 1 or 2 carbon atoms in each alkyl moiety; represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl, or represents cyclohexyl optionally substituted with 1 to 3 methyl substituents, in which RN has hydrogen, 1 or 2 carbon atoms; represents alkyl or benzyl optionally substituted with 1 to 3 identical or different substituents, in which case substituents on phenyl which may be mentioned include fluorine, chlorine and methyl, (2-Noano-2-oxyiminoacetyl)-amino acid derivatives of the formula (, I) and their geometric and optical isomers and isomer mixtures.

6. In formula (I), R1 is a group -B-CC)-NR"R
3, B represents a group -CH2-1-CH(CH3)- or -CH2CH2-, and R3 and R4 together with the nitrogen atom bonded to the nucleus form a 1.2- or 3-cyclic represents a heterocyclic or spiroheterocyclic group, where 2 represents oxygen or a CH2 group, z4 represents hydroxyl, methoxy, ethoxy, amino, methylamino, ethylamino, dimethylamino or ethylmethylamino, and m is 0 .1, 2.3 or 4, p represents 0, ■ or 2, q represents 0, ■, 2 or 3, and R is a carbon atom l or 2;
represents substituted alkyl having 1 to 4 carbon atoms, and examples of substituents that may be mentioned include halogen, alkylcarbonyl having 1 to 4 carbon atoms in the linear or branched alkyl moiety, -COOR', -CONR Is there a heterocyclic group of the formula "RmXOR" and [': R represents 1-cyclohexenyl, which in each case is further optionally substituted with 1 to 3 methyl substituents, RI is methyl, ethyl, n-
or represents 1-propyl, n-1i-1sec- or t-butyl, RII and Ro are the same or different, and hydrogen, methyl, ethyl, n
- or i-propyl, or optionally with chlorine and methyl as substituents, or identical or different substituents 1
represents benzyl optionally substituted with ~3 or represents alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety, in each case 1 or 2 carbon atoms in each alkyl moiety; represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having , or represents cyclohexyl optionally substituted with 1 to 3 methyl substituents, and Rm is hydrogen, 1 or 2 carbon atoms; alkyl or benzyl optionally substituted with 1 to 3 identical or different substituents, substituents on phenyl which may be mentioned in this case include fluorine, chlorine and methyl, as defined in point 1 above; formula(
I) (2-cyano-2-oxyiminoacetyl)-amino acid derivatives and their geometric and optical isomers and isomer mixtures.

7. In formula (I), R1 represents a group -A-C○○R2, and A represents a group -CH2-1-CH(CH3)- or -
CH2CH2-, B2 is methyl or ethyl, R is substituted alkyl having 1 or 2 carbon atoms, and possible substituents include Alkylcarbonyl having 1 to 4 carbon atoms in the branched alkyl moiety, -C
OOR', c ON RI I RI I I, o R
Is there a heterocyclic group of the formula IV and formula; R is further one 13! J- represents 1-cyclohexenyl, optionally substituted in each case with 1 to 3 methyl substituents, and R1 is methyl, ethyl, n- or i-propyl or n-1i-
1 sec- or t-butyl, RII' and RII' are the same or different, and represent hydrogen, methyl, ethyl, n- or i-propyl, or the same optionally having chlorine and methyl as substituents; or represents benzyl optionally substituted with 1 to 3 different substituents, or represents alkoxycarbonylalkyl having 1 or 2 carbon atoms in each alkyl moiety; carbon atom 1
or represents carbamoylalkyl, alkylcarbamoylalkyl or dialkylcarbamoylalkyl having 2 or cyclohexyl optionally substituted with 1 to 3 methyl substituents, and RV is hydrogen, 1 or 2 carbon atoms; represents alkyl or benzyl optionally substituted with 1 to 3 identical or different substituents, of which -140= substituents on phenyl which may be mentioned include fluorine, chlorine and methyl; (2-cyano-2-oxyiminoacetyl)-amino acid derivatives of formula (I) as described in 1 and their geometric and optical isomers and isomer mixtures.

8, -Formula (I) where R1 is a group -A-C○OR2 or -B-CONR
3R', A represents an optionally substituted linear or branched alkylene chain, and B represents an optionally substituted linear or branched alkylene chain; , R2 represents a substituent halogen, hydroxyl, alkoxy, acyloxy, optionally substituted aryl, optionally substituted cycloalkyl, and optionally substituted heterocycle; or R2 is further optionally substituted. represents optionally substituted cycloalkyl or optionally substituted cycloalkenyl; R3 represents hydrogen; or substituent halogen, cyano, -COOR', -CONRTIRTn, -NR"
Rm, -OR", -3(0), R", 7syl and in each case optionally substituted aryl, heterocycle,
represents optionally substituted alkyl with cycloalkyl and cycloalkenyl; or R3 represents in each case further optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocycle; , R4 represents hydrogen or a substituent halogen, cyano, -COOR', -CONRTIR", -NR"R
rr', -OR'N, -3(0), R'', 7syl and in each case optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl; or R4 also each represents an optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or group -OR'', or A and R2 are bonded to the nucleus crystal. B and R together with the atoms bonded to the nucleus represent a ring which may be optionally substituted, or B and R together with the atoms bonded to the nucleus crystal represent an optionally substituted ring; together with the nitrogen atom bonded to the nucleus crystal represents an optionally substituted heterocyclic group which may further contain a heteroatom, R is a substituent halogen, -COOR', -CONRII
RII+1-○RN1 represents a substituted alkyl having an optionally substituted heterocycle other than acyl and azolyl; or R represents an optionally substituted cycloalkenyl; R1 is hydrogen or a substituent represents halogen and optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl in each case, RII and RN are the same or different, and hydrogen or substituted Group halogen, -C
OORPj-1-CONR'R'' and in each case optionally substituted alkyl with optionally substituted aryl, cycloalkyl and cycloalkenyl; or RII and R1 further represent alkenyl, alkynyl or represents an optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocycle in each case or optionally substituted which together with the nitrogen atom bonded to the nucleus may further contain a heteroatom. (2-cyano-2-oxyiminoacetyl)-amino acid derivatives of In the preparation of its steric and optical isomers and isomer mixtures, a) - 2-cyano-2-oximino of the formula (II), in which R has the abovementioned meaning and R5 represents alkyl; - acetate of the formula (
III) R'-NR2(III) in which R1 has the meaning given above, is reacted with an amine of: b) - carboxyl of a carboxylic acid of formula (IV), in which R has the meaning given above; The activated derivative is prepared in the presence of a catalyst, if appropriate, and an acid binder, if appropriate, and a diluent, with the formula %(), where R1 has the meaning given above. , or react with an amine of the formula (V), where M represents hydrogen, an alkali metal ion, a protonated tertiary base or a quaternary ammonium, and R1 has the abovementioned meaning. , 2-cyano-2-oximino-acetamide of the formula (VD and R has the abovementioned meaning; d) - a substituted acetylamino acid ester of the formula (■) in which B, R and R5 have the abovementioned meaning; If appropriate in the presence of a diluent and if appropriate in the presence of a base, react with an amine of formula (■) in which R3 and R' have the meanings given above: e) - formula (H) in which R has the meaning given above and Q represents A or B, the latter having the meaning given above. If appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, the formula % formula % () in which Y represents an R20- or R3R'N- group, where R2, R3 and R4 are as defined above f) - the ammonium salt of 2-cyano-2-oximino-acetic acid of the formula (XI), having the meaning given above, in the presence of a diluent, if appropriate; In the presence of formula (IN)R'-CH
= O(ff) In the formula, R6-CH- group represents the above meaning of A or B, and an aldehyde of formula (xm) e
is reacted with 2-cyano-2-oxy-acetic acid of formula (IV), in which R has the meaning given above; and if appropriate in the presence of a diluent, react with an isocyanate of the formula % formula % (), in which R1 has the meaning given above; or h) - formula (
X V) The 2-cyano-2-oximino-acetamide of the formula, in which R has the abovementioned meaning, is reacted with a base, if appropriate in the presence of a diluent, and the resulting salt is reacted directly or, if appropriate, For example, after intermediate isolation, if appropriate in the presence of a diluent, the formula (XVl)R'-X
(XVI) wherein R1 and Method.

9. A pest control agent characterized in that it contains at least one amino acid derivative of the formula (%)-amino acid derivative as described in 1 and 8 above.

10. (2-cyano-2-oximino-acetyl) of the formula (■) described in 1 and 8 above when controlling pests
- Use of amino acid derivatives.

11. (2-cyano-
1. A method for controlling pests, which comprises applying a 2-oximino-acetyl)-amino acid derivative to the pests and/or their environment.

12. (2-cyano-
1. A method for producing a pest control agent, which comprises mixing a 2-oximino-acetyl)-amino acid derivative with an extender and/or a surfactant.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) In the formula, R^1 is a group -A-COOR^2 or -B-CO
NR^3R^4, A represents an optionally substituted linear or branched alkylene chain, and B represents an optionally substituted linear or branched alkylene chain. In the expression, R^2 is optionally substituted alkyl, and the substituent is halogen, hydroxyl, alkoxy, acyloxy, optionally substituted aryl, optionally substituted cycloalkyl, or optionally substituted cycloalkyl. R^2 represents an optionally substituted cycloalkyl or an optionally substituted cycloalkenyl; R^3 represents hydrogen or an optionally substituted alkyl; represented by the substituent halogen, cyano, -COO
R^I, -CONR^IIR^III, -NR^IIR^III
, -OR^IV, -S(O)_nR^IV, is acyl and in each case optionally substituted aryl, heterocycle, cycloalkyl or cycloalkenyl; or R^3 is further in each case represents optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocycle, R^4 represents hydrogen or optionally substituted alkyl, and the substituent is halogen, cyano ,-C
OOR^I, -CONR^IIR^III, -NR^IIR^
III, -OR^IV, -S(O)_nR^IV, represents acyl as well as optionally substituted aryl, heterocycle, cycloalkyl or cycloalkenyl in each case; or R^4 further represents each optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or group -
OR^IV, or A and R^2 together with the atoms to which they are bonded represent an optionally substituted ring, or B and R^3 together with the atoms to which they are bonded represents an optionally substituted ring, or R^
3 and R^4 together with the nitrogen atom to which they are bonded represent an optionally substituted heterocyclic group which may further contain a heteroatom, R represents a substituted alkyl, and the substituent is Halogen, -COOR^I, -CONR^IIR^III, -OR^
IV represents acyl and an optionally substituted heterocycle (excluding azolyl); or R represents an optionally substituted cycloalkenyl; R^I represents hydrogen or substituted alkyl; , the substituents represent halogen and in each case optionally substituted aryl, cycloalkyl and cycloalkenyl, R^II and R^IV are the same or different, and hydrogen or substituted is alkyl, and the substituent is halogen, -COOR^IV, -CONR^I R^IV
and in each case optionally substituted aryl, cycloalkyl and cycloalkenyl; or R^II and R^III further represent alkenyl, alkynyl or in each case optionally substituted cycloalkyl;
represents cycloalkenyl, aryl or heterocycle;
Alternatively, R^II and R^III together with the nitrogen atom to which they are bonded represent an optionally substituted heterocyclic group which may further contain a heteroatom, and R^IV represents hydrogen, alkyl, aralkyl or acyl. (2-cyano-2-oxyiminoacetyl)-amino acid derivatives and geometric and optical isomers and isomer mixtures thereof, where n represents the number 0, 1 or 2. 2. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) In the formula, R^1 is the group -A-COOR^2 or -B-CO
NR^3R^4, A represents an optionally substituted linear or branched alkylene chain, and B represents an optionally substituted linear or branched alkylene chain. In the expression, R^2 represents an optionally substituted alkyl, and the substituents include halogen, hydroxyl, alkoxy, acyloxy, an optionally substituted aryl, an optionally substituted cycloalkyl, and an optionally substituted cycloalkyl. or R^2 represents optionally substituted cycloalkyl or optionally substituted cycloalkenyl; R^3 represents hydrogen; or optionally substituted alkyl; and the substituent is halogen, cyano, -C
OOR^I, -CONR^IIR^III, -NR^IIR^
III, -OR^IV, -S(O)_nR^IV, acyl and optionally substituted aryl, heterocycle,
represents cycloalkyl or cycloalkenyl; or R^3 represents in each case further optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocycle; R^4 represents hydrogen; , or optionally substituted alkyl, and the substituent is halogen, cyano, -C
OOR^I, -CONR^IIR^III, -NR^IIR^
III, -OR^IV, -S(O)_nR^IV, stands for acyl and in each case optionally substituted aryl, heterocycle, cycloalkyl and cycloalkenyl; or R^4 can also represent each optionally substituted alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, heterocyclic or polycyclic carbocyclic group or group -
OR^IV, or A and R^2 together with the atoms to which they are bonded represent an optionally substituted ring, or B and R^3 together with the atoms to which they are bonded represents an optionally substituted ring, or R^
3 and R^4 together with the nitrogen atom to which they are bonded represent an optionally substituted heterocyclic group which may further contain a heteroatom, R represents an optionally substituted alkyl, and Substituents are halogen, -COOR^I, CONR^IIR^III,
-OR^IV, acyl and optionally substituted heterocycle (
(excluding azolyl); or R represents optionally substituted cycloalkenyl; R^I represents hydrogen or substituted alkyl, the substituents being halogen and in each case substituted represents aryl, cycloalkyl and cycloalkenylalkyl which may be
and hydrogen or optionally substituted alkyl,
The substituent is halogen, -COOR^IV, -CONR^
I stands for R^IV and in each case optionally substituted aryl, cycloalkyl and cycloalkenyl; or R^I and R^II can also be alkenyl, alkynyl or in each case substituted cycloalkyl,
represents cycloalkenyl, aryl or heterocycle;
Alternatively, R^II and R^III together with the bonded nitrogen atom represent an optionally substituted heterocyclic group which may further contain a heteroatom, and R^IV represents hydrogen, alkyl, aralkyl or acyl. and n represents a number of 0, 1 or 2, and a method for producing (2-cyano-2-oximinoacetyl)-amino acid derivatives and their steric and optical isomers and isomer mixtures, comprising: a ) General formula (II) ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (II) In the formula, R has the above meaning, and R^5 represents alkyl, 2-cyano-2-oximino-acetic acid The ester is reacted, if appropriate in the presence of a diluent and if appropriate in the presence of a base, with an amine of formula (III) R^1-NH_2(III) where R^1 has the meaning given above. b) General formula (IV) ▲Mathematical formulas, chemical formulas, tables, etc.▼(IV) In the formula, R has the above meaning, a carboxyl-activated derivative of a carboxylic acid of and if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent, of the formula (III) R^1-NH_2(III) in which R^1 has the meaning given above. c) General formula (V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(V) In the formula, M is hydrogen, an alkali metal ion, a protonated tertiary base, or a quaternary ammonium. 2-cyano-2-oximino-acetamide of formula (VI) R-, where R^1 represents X (VI) In the formula, X represents a halogen or sulfonyloxy group, and R has the above meaning; d) General formula (VII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ A substituted acetylamino acid ester of the formula (VII), in which B, R and R^5 have the abovementioned meanings, is prepared from a substituted acetylamino acid ester of the formula (VIII ) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (VIII) In the formula, R^3 and R^4 have the above meanings; e) General formula (IX) ▲ Numerical formulas, chemical formulas, Tables etc.▼(IX) in which R has the meaning given above and Q represents A or B, in which case they have the meaning given above, the carboxyl-activated acetyl- An amino acid, optionally in the presence of a catalyst, optionally an acid binder, and optionally a diluent, is converted into a compound of the formula (X) Y-H(X) where Y is R^2O- or R^3R^4N- group, where R^2, R^3 and R^4 have the above meanings; f) General formula (X I) ▲Mathematical formula, chemical formula , tables, etc. ▼ (X I ) where R has the above meaning, the ammonium salt of 2-cyano-2-oximino-acetic acid of the formula (XII), if appropriate in the presence of a diluent, is prepared. R^6-CH=O(XII) In the formula, the R^6-CH- group represents the above meaning of A or B, and the aldehyde of and formula (XIII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼( XIII) In the formula, R^4 has the above meaning, and is reacted with isonitrile; g) General formula (IV) ▲There are numerical formulas, chemical formulas, tables, etc.▼ (IV) In the formula, R has the above meaning 2-Cyano-2-oxy-acetic acid having the formula (XIV) R^1-NCO(XIV) in the presence of a catalyst, if appropriate, and a diluent, if appropriate, of the formula (XIV), R^ 1 has the above meaning; or h) General formula (XV) ▲ Numerical formula, chemical formula, table, etc. ▼ (XV) In the formula, R has the above meaning, 2- cyano-2-oximino-acetamide is reacted with a base, if appropriate in the presence of a diluent, and the resulting salt is reacted either directly or after intermediate isolation, if appropriate in the presence of a diluent, A method characterized by reacting with a compound of formula (XVI) R^1-X(XVI) in which R^1 and X have the above meanings. 3. A pest control agent comprising at least one (2-cyano-2-oxyiminoacetyl)-amino acid derivative of formula (I) according to claim 1 or 2. 4. Claim 1 or 2 for controlling pests
Use of (2-cyano-2-oximino-acetyl)-amino acid derivatives of formula (I) as described in Section 1.