US 12,655,116 B2Granted

Substituted isophthalic acid diamides

AssigneeBayer Aktiengesellschaft

InventorsChristian Waldraff, Ralf Braun, Arnim Köhn, Hartmut Ahrens, Uwe Döller, Elisabeth Asmus, Birgit Bollenbach-Wahl, Christopher Hugh Rosinger, Jan Dittgen, Anu Bheemaiah Machettira, Elmar Gatzweiler

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Estimating the term…

Abstract

Isophthalamides of the general formula (I) are described as herbicides. In this formula (I), X, Y and Z represent radicals such as hydrogen, alkyl and halogen. Q represents a heterocyclic ring such as tetrazolyl.

Claims17

Dependent claims

An isophthalamide of formula (I) or salt thereof

in which the symbols and indices are defined as follows:
Q is Q1,
X is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R1O, R2(O)nS or R1O—(C1-C6)-alkyl or R2S(O) n-(C1-C6)-alkyl,
Y is halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R1O or R2(O)nS,
R1 is (C1-C6)-alkyl, halo-(C1-C6)-alkyl or (C3-C6)-cycloalkyl,
R2 is (C1-C6)-alkyl,
Rx is (C1-C6)-alkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl or phenyl,
Z is hydrogen,
one of the following groups, each of which is substituted by s radicals from the group consisting of halogen, cyano, R1C(O), R1OC(O), R1O and R2(O)nS:
(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O—(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkenyl-(C1-C6)-alkyl, (C2-C6)-alkynyl, (C2-C6)-alkynyl-(C1-C6)-alkyl, (C1-C6)-alkoxy, R2S(O)n-(C1-C6)-alkyl, R1C(O), R1OC(O), R1C(O)—(C1-C6)-alkyl, R1OC(O)—(C1-C6)-alkyl, R1NH—(C1-C6)-alkyl, R12N—(C1-C6)-alkyl, R1NHC(O)—(C1-C6)-alkyl or R12NC(O)—(C1-C6)-alkyl,
or
one of the following groups, each substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, R1C(O) and R1OC(O):
phenyl or benzyl,
n is 0, 1 or 2, and
s is 0, 1, 2 or 3.

12 more elements

An isophthalamide of the formula (I-a) or salts thereof

wherein the symbols and indices are defined as follows:
No.
X
Y
Z
1-4
Me
Cl
Me
1-25
Me
CF3
Me
1-26
Me
CF3
Et
1-27
Me
CF3
c-Pr
1-28
Me
CF3
CH2-c-Pr
1-29
Me
CF3
CH2CF3
1-30
Me
CF3
CH2CHF2
1-31
Me
CF3
CH(Me)-c-Pr
1-32
Me
CF3
Pr
1-33
Me
CF3
i-Pr
1-34
Me
CF3
CH2CH2OMe
1-36
Me
CF3
CH2CN
1-44
Me
CHF2
Me
1-45
Me
CHF2
Et
1-46
Me
CHF2
c-Pr
1-47
Me
CHF2
CH2-c-Pr
1-49
Me
CHF2
CH2CHF2
1-56
OMe
CF3
Me
1-57
OMe
CF3
Et
1-58
OMe
CF3
c-Pr
1-72
OMe
CHF2
Me
1-73
OMe
CHF2
Et
1-74
OMe
CHF2
c-Pr
1-81
SMe
CF3
Me
1-82
SMe
CF3
Et
1-83
SMe
CF3
c-Pr
1-84
SMe
CF3
CH2-c-Pr
1-85
SMe
CF3
CH2CF3
1-86
SMe
CF3
CH2CHF2
1-87
SMe
CHF2
Me
1-88
SMe
CHF2
Et
1-89
SMe
CHF2
c-Pr
1-90
SMe
CHF2
CH2-c-Pr
1-92
SMe
CHF2
CH2CHF2
1-123
Cl
SO2Me
Me
1-125
Cl
SO2Me
c-Pr
1-129
Cl
CF3
Me
1-130
Cl
CF3
Et
1-131
Cl
CF3
c-Pr
1-132
Cl
CF3
CH2-c-Pr
1-133
Cl
CF3
CH2CF3
1-134
Cl
CF3
CH2CHF2
1-135
Cl
CF3
CH(Me)-c-Pr
1-136
Cl
CF3
Pr
1-137
Cl
CF3
iPr
1-138
Cl
CF3
CH2CH2OMe
1-140
Cl
CF3
CH2CN
1-142
Cl
CF3
CH2C(O)NMe2
1-143
Cl
CF3
Ph
1-146
Cl
CF3
cBu
1-147
Cl
CHF2
Me
1-148
Cl
CHF2
Et
1-149
Cl
CHF2
c-Pr
1-155
Cl
CHF2
iPr
1-156
Cl
CHF2
CH2CH2OMe
1-157
Cl
CHF2
CH2CH2SMe
1-158
Cl
CHF2
CH2CN
1-160
Cl
CHF2
CH2C(O)NMe2
1-161
Cl
CHF2
Ph
1-164
Cl
CHF2
cBu
1-165
Cl
C2F5
Me
1-166
Cl
C2F5
Et
1-173
Cl
Cl
c-Pr
1-177
Cl
Br
Me
1-178
Cl
Br
Et
1-179
Cl
Br
c-Pr
1-180
Cl
Br
CH2-c-Pr
1-181
Cl
Br
CH2CF3
1-182
Cl
Br
CH2CHF2
1-183
Cl
Br
CH(Me)-c-Pr
1-184
Cl
Br
Pr
1-185
Cl
Br
i-Pr
1-186
Cl
Br
CH2CH2OMe
1-195
Cl
I
Me
1-197
Cl
I
c-Pr
1-207
Br
CF3
Me
1-208
Br
CF3
Et
1-209
Br
CF3
c-Pr
1-210
Br
CF3
CH2-c-Pr
1-211
Br
CF3
CH2CF3
1-212
Br
CF3
CH2CHF2
1-225
Br
CHF2
Me
1-226
Br
CHF2
Et
1-227
Br
CHF2
c-Pr
1-228
Br
CHF2
CH2-c-Pr
1-229
Br
CHF2
CH2CF3
1-230
Br
CHF2
CH2CHF2
1-271
Et
CF3
Me
1-272
Et
CF3
Et
1-273
Et
CF3
c-Pr
1-274
Et
CF3
CH2-c-Pr
1-276
Et
CF3
CH2CHF2
1-277
Et
CHF2
Me
1-278
Et
CHF2
Et
1-279
Et
CHF2
c-Pr
1-287
c-Pr
CF3
Et
1-288
c-Pr
CF3
c-Pr
1-289
c-Pr
CF3
CH2-c-Pr
1-291
c-Pr
CF3
CH2CHF2
1-292
c-Pr
CF3
CH(Me)-c-Pr
1-304
c-Pr
CHF2
Me
1-305
c-Pr
CHF2
Et
1-306
c-Pr
CHF2
c-Pr
1-337
Cl
CF3
acetyl
1-338
Cl
CF3
H
1-339
Me
CHF2
CH(Me)-c-Pr
1-340
Br
CHF2
CH(Me)-c-Pr
1-341
Et
CF3
CH(Me)-c-Pr
1-342
Br
Br
Me
1-343
Br
Br
Et
1-344
Br
Br
c-Pr
1-345
Me
CHF2
Pr
1-346
Me
CHF2
i-Pr
1-347
Me
CHF2
CH2CH2OMe
1-349
Br
Cl
Me
1-350
Br
Cl
Et
1-351
Br
Cl
c-Pr
1-352
SMe
CF3
CH(Me)-c-Pr
1-353
SMe
CHF2
CH(Me)-c-Pr
1-354
Cl
OMe
Me
1-355
Cl
OMe
Et
1-356
Cl
OMe
c-Pr.

490 more elements

An isophthalamide of the formula (I-b) or salts thereof

wherein the symbols and indices are defined as follows:
No.
X
Y
Z
2-25
Me
CF3
Me
2-26
Me
CF3
Et
2-27
Me
CF3
c-Pr
2-28
Me
CF3
CH2-c-Pr
2-29
Me
CF3
CH2CF3
2-30
Me
CF3
CH2CHF2
2-31
Me
CF3
CH(Me)-c-Pr
2-32
Me
CF3
Pr
2-33
Me
CF3
i-Pr
2-34
Me
CF3
CH2CH2OMe
2-35
Me
CF3
CH2CH2SMe
2-36
Me
CF3
CH2CN
2-42
Me
CF3
c-Bu
2-44
Me
CHF2
Me
2-45
Me
CHF2
Et
2-46
Me
CHF2
c-Pr
2-47
Me
CHF2
CH2-c-Pr
2-49
Me
CHF2
CH2CHF2
2-56
OMe
CF3
Me
2-57
OMe
CF3
Et
2-58
OMe
CF3
c-Pr
2-72
OMe
CHF2
Me
2-73
OMe
CHF2
Et
2-74
OMe
CHF2
c-Pr
2-81
SMe
CF3
Me
2-82
SMe
CF3
Et
2-83
SMe
CF3
c-Pr
2-84
SMe
CF3
CH2-c-Pr
2-86
SMe
CF3
CH2CHF2
2-87
SMe
CHF2
Me
2-88
SMe
CHF2
Et
2-89
SMe
CHF2
c-Pr
2-90
SMe
CHF2
CH2-c-Pr
2-92
SMe
CHF2
CH2CHF2
2-123
Cl
SO2Me
Me
2-125
Cl
SO2Me
c-Pr
2-129
Cl
CF3
Me
2-130
Cl
CF3
Et
2-131
Cl
CF3
c-Pr
2-132
Cl
CF3
CH2-c-Pr
2-133
Cl
CF3
CH2CF3
2-134
Cl
CF3
CH2CHF2
2-135
Cl
CF3
CH(Me)-c-Pr
2-138
Cl
CF3
CH2CH2OMe
2-142
Cl
CF3
CH2C(O)NMe2
2-143
Cl
CF3
Ph
2-146
Cl
CF3
c-Bu
2-147
Cl
CHF2
Me
2-148
Cl
CHF2
Et
2-149
Cl
CHF2
c-Pr
2-154
Cl
CHF2
Pr
2-155
Cl
CHF2
i-Pr
2-156
Cl
CHF2
CH2CH2OMe
2-157
Cl
CHF2
CH2CH2SMe
2-158
Cl
CHF2
CH2CN
2-160
Cl
CHF2
CH2C(O)NMe2
2-161
Cl
CHF2
Ph
2-164
Cl
CHF2
c-Bu
2-173
Cl
Cl
c-Pr
2-177
Cl
Br
Me
2-178
Cl
Br
Et
2-179
Cl
Br
c-Pr
2-180
Cl
Br
CH2-c-Pr
2-181
Cl
Br
CH2CF3
2-182
Cl
Br
CH2CHF2
2-183
Cl
Br
CH(Me)-c-Pr
2-184
Cl
Br
Pr
2-185
Cl
Br
i-Pr
2-186
Cl
Br
CH2CH2OMe
2-195
Cl
I
Me
2-196
Cl
I
Et
2-197
Cl
I
c-Pr
2-207
Br
CF3
Me
2-208
Br
CF3
Et
2-210
Br
CF3
CH2-c-Pr
2-211
Br
CF3
CH2CF3
2-212
Br
CF3
CH2CHF2
2-213
Br
CF3
CH(Me)-c-Pr
2-225
Br
CHF2
Me
2-226
Br
CHF2
Et
2-227
Br
CHF2
c-Pr
2-228
Br
CHF2
CH2-c-Pr
2-229
Br
CHF2
CH2CF3
2-230
Br
CHF2
CH2CHF2
2-271
Et
CF3
Me
2-272
Et
CF3
Et
2-273
Et
CF3
c-Pr
2-276
Et
CF3
CH2CHF2
2-277
Et
CHF2
Me
2-278
Et
CHF2
Et
2-279
Et
CHF2
c-Pr
2-286
c-Pr
CF3
Me
2-287
c-Pr
CF3
Et
2-288
c-Pr
CF3
c-Pr
2-289
c-Pr
CF3
CH2-c-Pr
2-291
c-Pr
CF3
CH2CHF2
2-292
c-Pr
CF3
CH(Me)-c-Pr
2-304
c-Pr
CHF2
Me
2-305
c-Pr
CHF2
Et
2-306
c-Pr
CHF2
c-Pr
2-337
Cl
CF3
acetyl
2-338
Cl
CF3
H
2-339
Me
CHF2
CH(Me)-c-Pr
2-340
Br
CHF2
CH(Me)-c-Pr
2-341
Et
CF3
CH(Me)-c-Pr
2-342
Br
Br
Et
2-343
Br
Br
c-Pr
2-344
Me
CHF2
Pr
2-345
Me
CHF2
i-Pr
2-346
Me
CHF2
CH2CH2OMe
2-347
Me
CHF2
CH2CH2SMe
2-348
Br
Cl
Et
2-349
Br
Cl
c-Pr
2-350
SMe
CF3
CH(Me)-c-Pr
2-351
SMe
CHF2
CH(Me)-c-Pr
2-352
Cl
OMe
Me
2-353
Cl
OMe
Et
2-354
Cl
OMe
c-Pr.

474 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/916,836Filed 1 Apr 2021
Priority: EP 201683497 Apr 2020
Published: US 2023/0159472 A125 May 2023
Granted: 16 Jun 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 257/06
Five-membered rings: with nitrogen atoms directly attached to the ring carbon atom
A01N 43/713
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having rings with four or more nitrogen…
A01P 13/00
Herbicides
C07D 271/08
Not condensed with other rings: 1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles

Family

US 2023/0159472 A1Pre-grant publication · published 25 May 2023
US 12,655,116 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

17/916,836Filed 1 Apr 2021

Priority

EP 201683497 Apr 2020

Published

US 2023/0159472 A125 May 2023

Granted

16 Jun 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 257/06
Five-membered rings: with nitrogen atoms directly attached to the ring carbon atom
A01N 43/713
Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds: having rings with four or more nitrogen…
A01P 13/00
Herbicides
C07D 271/08
Not condensed with other rings: 1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles