# US 12,180,187 B2 · 1-phenyl-5-azinylpyrazolyl-3-oxyalkyl acids and their use for controlling unwanted plant growth

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- Number: US 12,180,187 B2
- Document ID: US12180187B2
- Status: Granted
- Kind: B2
- Application number: 17/615,786
- Filed: 2020-05-29
- Published: 2022-07-28
- Granted: 2024-12-31
- Earliest claimed: 2019-06-03
- Assignees: Bayer Aktiengesellschaft
- Applicants: Bayer Aktiengesellschaft
- Inventors: Michael Gerhard Hoffmann; Estella Buscato Arsequell; Harald Jakobi; Thomas Mueller; Erin Nicole Smith; Elisabeth Asmus; Anu Bheemaiah Machettira; Elmar Gatzweiler; Christopher Hugh Rosinger; Dirk Schmutzler
- Web page: https://patentgrep.com/patent/US12180187B2

## CPC

- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/56: 1,2-Diazoles; Hydrogenated 1,2-diazoles
- A01N 43/58: 1,2-Diazines; Hydrogenated 1,2-diazines
- A01N 43/60: 1,4-Diazines; Hydrogenated 1,4-diazines
- A01N 43/66: 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N 43/707: 1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
- A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
- A01P 13/02: selective
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/14: containing three or more hetero rings
- C07D 405/14: containing three or more hetero rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01P: BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS

## Abstract

What are described are compounds of the general formula (I) and agrochemically acceptable salts thereof and their preparation and their use in the crop protection sector.

## Claims

### Claim 1

A Compound of formula (I)
And/or an agrochemically acceptable salt thereof, where
A is selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nNR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of hydrogen, halogen, cyano, nitro, OR5, S(O)nNR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono- to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl; and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO; and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl; and
NH2;
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6; and
s is 0, 1 or 2.

### Claim 2 (depends on 1)

The Compound according to claim 1, wherein
A is selected from the group consisting of
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—; and
aryl-(C1-C4)-alkyl, where the aryl is unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 represents hydrogen, or (C1-C4)-alkyl;
R10 is selected from the group consisting of
hydrogen, aryl, (C1-C4)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C4)-alkyl, (C2-C4)-alkenyl, S(O)nR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, and NR6COR8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of
S(O)nR5, SO2NR6R7, CO2R8, and NR6CO2R8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono-to hexasubstituted by radicals from the group consisting of halogen, (C1-C4)-alkyl, and OR5, and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C4)-alkyl, (C3-C6)-cycloalkyl or (C1-C4)-haloalkyl;
R6 represents hydrogen or R5;
R7 represents hydrogen or (C1-C4)-alkyl;
R8 represents hydrogen or (C1-C4)-alkyl;
R2 is selected from the group consisting of
hydrogen, cyano;
(C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C6)-alkoxy;
(C3-C6)-cycloalkyl, and (C1-C6)-alkyl-(C1-C3)-alkoxy;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C2)-alkyloxycarbonyl, (C1-C3)-alkoxy, (C1-C6)-haloalkoxy;
(C1-C6)-alkylthio, (C1-C6)-haloalkylthio;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl; and
S(O)n—(C1-C2)-alkyl where n=1 or 2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, fluorine, chlorine, bromine;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy; and
(C1-C6)-alkoxy;
R12 is selected from the group consisting of
hydrogen, halogen, cyano;
(C1-C6)-alkyl, (C1-C6)-haloalkyl;
(C1-C6)-alkoxy, and (C1-C3)-haloalkoxy;
and where the running number
m is 0 or 1;
n is 0, 1 or 2;
o is 0 or 1;
p is 0;
r is 6; and
s is 0 or 1.

### Claim 3 (depends on 1)

The Compound according to claim 1, wherein
A is selected from the group consisting of
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-alkoxy; and
aryl-(C1-C4)-alkyl, where the aryl is substituted by (C1-C6)-alkyl;
R9 represents hydrogen;
R10 is selected from the group consisting of
aryl, (C1-C12)-alkyl, (C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl, (C2-C12)-alkenyl, S(O)nR5, SO2NR6R7, CO2R8, and NR6R8,
which are unsubstituted or where the alkyl, cycloalkyl, alkenyl, cycloalkenyl and alkynyl radicals mentioned above are in each case independently of one another substituted by m radicals selected from the group consisting of S(O)nR5, SO2NR6R7, CO2R8, and NR6CO2R8;
or
R9 and R10 together with the nitrogen atom to which they are attached form an unsubstituted saturated, partially or fully unsaturated five-, six- or seven-membered ring which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl or (C1-C6)-haloalkyl;
R6 represents hydrogen;
R7 represents hydrogen or (C1-C6)-alkyl;
R8 represents (C1-C6)-alkyl;
R2 is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, and (C1-C4)-alkoxy;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-haloalkoxy; and
(C1-C6)-alkylthio;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, fluorine, chlorine, bromine;
methyl, ethyl, CF3, and OCF3;
R12 is selected from the group consisting of
hydrogen, fluorine, chlorine, cyano;
methyl, ethyl, CF3, and OCF3;
and where the running number
m is 0 or 1;
n is 0, 1 or 2;
o is 1;
p is 0;
r is 6; and
s is 0 or 1.

### Claim 4 (depends on 1)

The Compound according to claim 1, wherein
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
methyl and ethyl;
allyl and propargyl; and
PhCH2;
R9 represents hydrogen and
R10 is selected from the group consisting of (C1-C12)-alkyl, S(O)nR5, SO2NR6R7, and CO2R8, which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of S(O)nR5, SO2NR6R7, CO2R8, and NR6CO2R8;
R5 represents ethyl, methyl, CF3, or CH2CF3;
R6 represents hydrogen or R5;
R7 represents hydrogen, methyl or ethyl;
R8 represents methyl or ethyl;
R2 is selected from the group consisting of
hydrogen;
methyl, and ethyl;
R3 is selected from the group consisting of
hydrogen, fluorine, bromine, chlorine, cyano, NO2;
methyl, CF3, and OCF3;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of hydrogen, fluorine and chlorine;
R12 is selected from the group consisting of
hydrogen, fluorine, chlorine, cyano;
methyl, CF3, and OCF3.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein
R3 is selected from the group consisting of
fluorine, chlorine, bromine, iodine, cyano, NO2; and
CF3.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein R4 represents phenyl which is mono- or polysubstituted by fluorine and/or chlorine.

### Claim 7 (depends on 1)

The compound of the general formula (I) according to claim 1, wherein
R12 is selected from the group consisting of
fluorine, chlorine, bromine, cyano, NO2;
CF3.

### Claim 8 (depends on 1)

The compound
according to claim 1, wherein the chiral carbon atom marked by (*) has an (R) configuration.

### Claim 9 (depends on 1)

The compound
according to claim 1, wherein the chiral carbon atom marked by (*) has an(S) configuration.

### Claim 10

A process for preparing the compound of formula (I) and/or an agrochemically acceptable salt thereof and/or agrochemically acceptable quaternized nitrogen derivative thereof
comprising
alkylation of the compound of formula (II)
with a halide of formula (III)
in the presence of a base.

### Claim 11 (depends on 1)

An herbicidal composition and/or plant growth-regulating composition, comprising one or more compounds according to claim 1.

### Claim 12 (depends on 1)

A method of controlling harmful plants and/or regulating the growth of plants, comprising applying an effective amount of one or more compounds according to claim 1 to one or more plants, plant parts, plant seeds and/or an area under cultivation.

### Claim 13 (depends on 1)

A product comprising the compound of according to claim 1 as an herbicide and/or as plant growth regulator.

### Claim 14 (depends on 13)

A product according to claim 13, wherein the compound is used to control one or more harmful plants and/or to regulate growth of one or more plants in one or more crops of useful plants or ornamental plants.

### Claim 15 (depends on 13)

The product according to claim 13, wherein the crop plants are transgenic crop plants.

### Claim 16

A compound of formula (II) and/or salt thereof
where,
A is selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of
hydrogen, halogen, cyano, nitro, OR5, S(O)nR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono-to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl; and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO; and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl; and
NH2;
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6; and
s is 0, 1 or 2.

### Claim 17 (depends on 16)

A process for preparing the compound of claim 16
comprising a reaction of an electrophile with a 3-hydroxypyrazole of the formula (IIa)
and comprising reacting a compound of formula (VIII)
in a solvent
in the presence of a metal halide.

### Claim 18

A process for preparing a compound of formula (VIII) where A is
selected from the group consisting of A1-A15,
R1 is selected from the group consisting of
OR1a and
NR9R10; where
R1a is selected from the group consisting of
hydrogen;
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, which is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C1-C6)-haloalkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkoxy, cyano and nitro;
(C2-C4)-alkenyl, (C2-C4)-alkynyl;
(C1-C4)-alkyl-SO—(C1-C4)—, (C1-C4)-alkyl-SO2—(C1-C4)—;
heterocyclyl-(C1-C4)-alkyl, heteroaryl-(C1-C4)-alkyl and aryl-(C1-C4)-alkyl, where the aryl, heterocyclyl and heteroaryl are unsubstituted or substituted by halogen, (C1-C6)-alkyl and/or (C1-C6)-haloalkyl;
R9 is selected from the group consisting of hydrogen, and (C1-C12)-alkyl;
R10 is selected from the group consisting of
hydrogen;
aryl, heteroaryl, heterocyclyl;
(C1-C12)-alkyl;
(C3-C8)-cycloalkyl, (C3-C7)-cycloalkyl-(C1-C7)-alkyl;
(C2-C12)-alkenyl, (C5-C7)-cycloalkenyl, (C2-C12)-alkynyl;
S(O)nR5, cyano, nitro, OR5, SO2NR6R7, CO2R8, COR8, NR6R8, NR6COR8, NR6CO2R8, and NR6SO2R8;
which are unsubstituted or in each case independently of one another substituted by m radicals selected from the group consisting of
hydrogen, halogen, cyano, nitro, OR5, S(O)nR5, SO2NR6R7, CO2R8, CONR6R8, COR6, NR6R8, NR6COR8, NR6CONR8R8, NR6CO2R8, NR6SO2R8, NR6SO2NR6R8, and C(R6)═NOR8;
or
R9 and R10 together with the nitrogen atom to which they are attached form a saturated, partially or fully unsaturated five-, six- or seven-membered ring which is optionally mono-to hexasubstituted by radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, OR5, S(O)nR5, CO2R8, CONR6R8, COR6 and C(R6)═NOR8 and which, in addition to this nitrogen atom, contains r carbon atoms, o oxygen atoms, p sulfur atoms and q elements from the group consisting of NR7, CO and NCOR7 as ring atoms;
R5 represents (C1-C8)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-haloalkyl or aryl;
R6 represents hydrogen or R5;
R7 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R8 represents hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C4)-alkenyl or (C3-C4)-alkynyl;
R2 is selected from the group consisting of
hydrogen and cyano;
(C1-C6)-alkyl, (C1-C4)-alkoxy-(C1-C4)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkoxy;
(C2-C6)-alkenyl, (C2-C6)-haloalkenyl;
(C2-C6)-alkynyl, (C2-C6)-haloalkynyl; and
(C3-C6)-cycloalkyl;
R3 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl;
(C1-C2)-alkyl-S(O)n and (C1-C2)-haloalkyl-S(O)n;
CHO; and
NH2;
R4 represents phenyl, where the phenyl radical is unsubstituted or mono- or polysubstituted by a radical selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, nitro;
(C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C3)-haloalkoxy;
(C2-C3)-alkenyl, halo-(C2-C3)-alkenyl, (C1-C6)-alkoxy;
(C2-C3)-alkynyl, halo-(C2-C3)-alkynyl, (C1-C4)-alkyl-S(O)n;
CHO, (C1-C4)-alkyloxycarbonyl and NH2;
R12 is selected from the group consisting of
hydrogen, halogen, cyano, isocyanato, NO2;
(C1-C6)-alkyl, (C1-C6)-haloalkyl, (C1-C6)-alkylcarbonyl, (C1-C6)-haloalkylcarbonyl, (C1-C4)-alkyloxycarbonyl, (C1-C6)-alkoxy, (C1-C3)-haloalkoxy, (C1-C4)-alkyl-S(O)n;
(C2-C3)-alkenyl, (C2-C3)-haloalkenyl;
(C2-C3)-alkynyl, (C2-C3)-haloalkynyl; and
NH2:
and where the running number
m is 0, 1 or 2;
n is 0, 1 or 2;
o is 0, 1 or 2;
p is 0 or 1;
q is 0 or 1;
r is 3, 4, 5 or 6; and
s is 0, 1 or 2,
comprising a reaction of an azine-A-substituted propynoic acid of formula (VI)
with a compound of formula (VII)
in a solvent
in the presence of an amide coupling reagent.

### Claim 19 (depends on 16)

A product comprising a compound of formula (II) and/or a salt thereof according to claim 16 for preparing an agrochemically active compound.

### Claim 20 (depends on 16)

A product comprising a compound of according to claim 16, as intermediate for preparation of one or more fine chemicals and/or active compounds for agriculture.