# US 12,599,136 B2 · Substituted isophthalic acid diamides and their use as herbicides

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- Number: US 12,599,136 B2
- Document ID: US12599136B2
- Status: Granted
- Kind: B2
- Application number: 17/995,662
- Filed: 2021-04-01
- Published: 2023-06-15
- Granted: 2026-04-14
- Earliest claimed: 2020-04-07
- Assignees: Bayer Aktiengesellschaft
- Applicants: Bayer Aktiengesellschaft
- Inventors: Christian Waldraff; Ralf Braun; Arnim Koehn; Hartmut Ahrens; Elisabeth Asmus; Birgit Bollenbach-Wahl; Christopher Hugh Rosinger; Elmar Gatzweiler; Jan Dittgen; Anu Bheemaiah Machettira
- Web page: https://patentgrep.com/patent/US12599136B2

## CPC

- A01N 43/713: having rings with four or more nitrogen atoms as the only ring hetero atoms
- A01P 13/00: Herbicides; Algicides
- A01P 21/00: Plant growth regulators
- C07D 257/06: with nitrogen atoms directly attached to the ring carbon atom
- C07D 271/08: 1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- 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
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

There are described isophthalamides of the general formula (I) as herbicides. In this formula (I) X and Y are radicals such as hydrogen, alkyl and halogen. Z1 and Z2 are radicals such as alkyl, cycloalkyl and phenyl. Q is a heterocyclic ring such as tetrazolyl.

## Claims

### Claim 1

An isophthalamide of formula (I) or salt thereof
in which the symbols and indices are defined as follows:
Q is Q1,
Rx is (C1-C6)-alkyl,
W is nitrogen,
X is halogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl,
Y is halogen, halo-(C1-C6)-alkyl, or R2(O)2S,
with the proviso that Y is not R2(O)2S when X is halogen,
Z1, Z2 are independently one of the following groups, each of which is substituted by 0, 1, 2, 3, or 4 halogen: (C1-C6)-alkyl, (C3-C6)-cycloalkyl, or (C3-C6)-cycloalkyl-(C1-C6)-alkyl,
or
phenyl substituted by halogen or (C1-C6)-alkyl,
or
Z1 and Z2, together is (CH2)4 or forms a pyrazol-1-yl or L-prolin-1-yl ethyl ester with the nitrogen to which they are connected
and
R2 is methyl, ethyl, n-propyl, or isopropyl.

### Claim 2 (depends on 1)

An isophthalamide or salt as claimed in claim 1, in which
Q is Q1,
Rx is Me, Et, Pr, or i-Pr,
W is nitrogen,
X is halogen, (C1-C6)-alkyl, or c-Pr,
Y is halogen, halo-(C1-C6)-alkyl, or SO2Me, with the proviso that Y is not methylsulfonyl when X is halogen,
Z1, Z2 are independently (C1-C6)-alkyl, (C3-C6)-cycloalkyl, CH2cPr, (C1-C6)-alkyl substituted by 0, 1, 2, 3, or 4 halogen, Ph, or (2-Me)Ph,
or Z1 and Z2 together is (CH2)4,
or W, Z1 and Z2 together are pyrazol-1-yl or L-prolin-1-yl ethyl ester, and
c-Pr represents cyclo-propyl.

### Claim 3 (depends on 1)

An isophthalamide or salt as claimed in claim 1, in which
Q is Q1,
Rx is Me, Et or Pr,
W is nitrogen,
X is F, Cl, Br, I, Me, Et, or c-Pr,
Y is F, Cl, Br, I, SO2Me, CHF2, CF3 or C2F5,
with the proviso that Y is not methylsulfonyl when X is halogen,
Z1, Z2 are independently Me, Et, c-Pr, CH2-c-Pr, CH2CHF2, CH2CF3 Ph or (2-Me)Ph,
or Z1 and Z2 together are (CH2)4,
or W, Z1 and Z2 together are pyrazol-1-yl or L-prolin-1-yl ethyl ester, and
c-Pr represents cyclo-propyl.

### Claim 4 (depends on 1)

A herbicidal composition or plant growth-regulating composition comprising one or more isophthalamides of formula (I) or salts thereof as claimed in claim 1.

### Claim 5 (depends on 4)

The herbicidal composition as claimed in claim 4, further comprising a formulation auxiliary.

### Claim 6 (depends on 4)

The herbicidal composition as claimed in claim 4, comprising at least one further active ingredient from the group of insecticides, acaricides, herbicides, fungicides, safeners and/or growth regulators.

### Claim 7 (depends on 4)

The herbicidal composition as claimed in claim 4, comprising a safener.

### Claim 8 (depends on 7)

The herbicidal composition as claimed in claim 7, in which the safener is selected from the group consisting of mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, benoxacor and dichlormid.

### Claim 9 (depends on 1)

A method of controlling one or more unwanted plants, comprising applying an effective amount of at least one isophthalamide of the formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof to the plants and/or to a site of unwanted vegetation.

### Claim 10 (depends on 1)

A product comprising a compound of formula (I) or salt as claimed in claim 1 or a herbicidal composition thereof for controlling one or more unwanted plants.

### Claim 11

An isophthalamide of the formula (I-a) or salts thereof
in which the symbols and indices are defined as follows:
No.
X
Y
W
Z1
Z2
1-19
Me
CF3
N
Me
Me
1-20
Me
CF3
N
Me
Et
1-21
Me
CF3
N
Me
c-Pr
1-24
Me
CF3
N
Me
CH2CHF2
1-31
Me
CF3
N
Et
Et
1-32
Me
CF3
N
Et
c-Pr
1-40
Me
CF3
N
c-Pr
c-Pr
1-50
Me
CHF2
N
Me
Me
1-51
Me
CHF2
N
Me
Et
1-59
Me
CHF2
N
Et
Et
1-123
Cl
CF3
N
Me
Me
1-124
Cl
CF3
N
Me
Et
1-125
Cl
CF3
N
Me
c-Pr
1-126
Cl
CF3
N
Me
CH2-c-Pr
1-128
Cl
CF3
N
Me
CH2CHF2
1-135
Cl
CF3
N
Et
Et
1-136
Cl
CF3
N
Et
c-Pr
1-144
Cl
CF3
N
c-Pr
c-Pr
1-152
Cl
CF3
N
—(CH2)4—
1-153
Cl
CF3
pyrazol-1-yl
1-154
Cl
CHF2
N
Me
Me
1-155
Cl
CHF2
N
Me
Et
1-156
Cl
CHF2
N
Me
c-Pr
1-159
Cl
CHF2
N
Me
CH2CHF2
1-166
Cl
CHF2
N
Et
Et
1-167
Cl
CHF2
N
Et
c-Pr
1-175
Cl
CHF2
N
c-Pr
c-Pr
1-191
Cl
Br
N
Me
Me
1-192
Cl
Br
N
Me
Et
1-200
Cl
Br
N
Et
Et
1-395
Me
SO2Me
N
Me
Me
1-398
Cl
C1
N
Me
Ph
1-399
Cl
Cl
N
Me
(2-Me)Ph
1-400
Cl
CF3
1-401
Me
CF3
1-402
Cl
CHF2
and
c-Pr represents cyclopropyl.

### Claim 12

An isophthalamide of the formula (I-a) or salts thereof
in which the symbols and indices are defined as follows:
No.
X
Y
W
Z1
Z2
1-123
Cl
CF3
N
Me
Me
1-154
Cl
CHF2
N
Me
Me

### Claim 13

An isophthalamide of the formula (I-b) or salts thereof
in which the symbols and indices are defined as follows:
No.
X
Y
W
Z1
Z2
2-19
Me
CF3
N
Me
Me
2-21
Me
CF3
N
Me
c-Pr
2-31
Me
CF3
N
Et
Et
2-32
Me
CF3
N
Et
c-Pr
2-50
Me
CHF2
N
Me
Me
2-51
Me
CHF2
N
Me
Et
2-59
Me
CHF2
N
Et
Et
2-123
CI
CF3
N
Me
Me
2-124
Cl
CF3
N
Me
Et
2-125
Cl
CF3
N
Me
c-Pr
2-126
Cl
CF3
N
Me
CH2-c-Pr
2-128
Cl
CF3
N
Me
CH2CHF2
2-135
Cl
CF3
N
Et
Et
2-136
Cl
CF3
N
Et
c-Pr
2-144
Cl
CF3
N
c-Pr
c-Pr
2-152
Cl
CF3
N
—(CH2)4—
2-153
Cl
CF3
pyrazol-1-yl
2-154
Cl
CHF2
N
Me
Me
2-155
Cl
CHF2
N
Me
Et
2-156
Cl
CHF2
N
Me
c-Pr
2-159
Cl
CHF2
N
Me
CH2CHF2
2-166
Cl
CHF2
N
Et
Et
2-167
Cl
CHF2
N
Et
c-Pr
2-175
Cl
CHF2
N
c-Pr
c-Pr
2-191
Cl
Br
N
Me
Me
2-192
Cl
Br
N
Me
Et
2-200
Cl
Br
N
Et
Et
2-340
c-Pr
CF3
N
Me
c-Pr
2-398
Cl
CF3
2-399
Me
CF3
and
c-Pr presents cyclopropyl.

### Claim 14

An isophthalamide of the formula (I-b) or salts thereof
in which the symbols and indices are defined as follows:
No.
X
Y
W
Z1
Z2
2-123
Cl
CF3
N
Me
Me
2-154
Cl
CHF2
N
Me
Me

### Claim 15

An isophthalamide of the formula (I-c) or salts thereof
No.
X
Y
W
Z1
Z2
3-123
Cl
CF3
N
Me
Me
3-124
Cl
CF3
N
Me
Et
3-126
Cl
CF3
N
Me
CH2-c-Pr
3-152
Cl
CF3
N
—(CH2)4—
3-153
Cl
CF3
pyrazol-1-yl
and
c-Pr represents cyclopropyl.