IP Library Granted Patent US 9,198,425
Granted Patent B2
US 9,198,425 · App. 14/379,528 · Granted Dec 1, 2015

Herbicidally-effective sulfinyl aminobenzamides

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Quick Facts
Patent No.
US 9,198,425
App. No.
14/379,528
Granted
Dec 1, 2015
Kind
B2
Abstract

Sulfinylaminobenzamides of the general formula (I) as herbicides are described. In this formula (I), R, R′, R″, X, W and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. Q is a tetrazolyl, triazolyl or oxadiazolyl radical.

Claims (73)

1. A sulfinylaminobenzamide of the formula (I) and/or a salt thereof

in which

Q is a Q3 radical,

X is nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 ) -alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 ) -alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 (R 1 ON═)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 (R 1 O)N(O)C, (R 1 ) 2 N(R 1 )N(O)C, R 1 (O)C(R 1 )N(O)C, R 2 O(O)C(R 1 )N(O)C, (R 1 ) 2 N(O)C(R 1 )N(O)C, R 2 (O) 2 S(R 1 )N(O)C, R 1 O(O) 2 S(R 1 )N(O)C, (R 1 ) 2 N(O) 2 S(R 1 )N(O)C, R 1 O, R 1 (O)CO, R 2 (O) 2 SO, R 2 O(O)CO, (R 1 ) 2 N(O)CO, (R 1 ) 2 N, R 1 (O)C(R 1 )N, R 2 (O) 2 S(R 1 )N, R 2 O(O)C(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 1 O(O) 2 S(R 1 )N, (R 1 ) 2 N(O) 2 S(R 1 )N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S, R 1 (O)C(R 1 )N(O) 2 S, R 2 O(O)C(R 1 )N(O) 2 S, (R 1 ) 2 N(O)C(R 1 )N(O) 2 S, (R 5 O) 2 (O)P, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, (R 1 O)(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, R 1 (O)CO—(C 1 -C 6 )-alkyl, R 2 (O) 2 SO—(C 1 -C 6 )-alkyl, R 2 O(O)CO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)CO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, (R 5 O) 2 (O)P—(C 1 -C 6 )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl-(C 1 -C 6 )-alkyl, where the six latter radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

Z is hydrogen, nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 (R 1 ON═)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 (R 1 O)N(O)C, (R 1 ) 2 N(R 1 )N(O)C, R 1 (O)C(R 1 )N(O)C, R 2 O(O)C(R 1 )N(O)C, (R 1 ) 2 N(O)C(R 1 )N(O)C, R 2 (O) 2 S(R 1 )N(O)C, R 1 O(O) 2 S(R 1 )N(O)C, (R 1 ) 2 N(O) 2 S(R 1 )N(O)C, R 1 O, R 1 (O)CO, R 2 (O) 2 SO, R 2 O(O)CO, (R 1 ) 2 N(O)CO, (R 1 ) 2 N, R 1 (O)C(R 1 )N, R 2 (O) 2 S(R 1 )N, R 2 O(O)C(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 1 O(O) 2 S(R 1 )N, (R 1 ) 2 N(O) 2 S(R 1 )N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S, R 1 (O)C(R 1 )N(O) 2 S, R 2 O(O)C(R 1 )N(O) 2 S, (R 1 ) 2 N(O)C(R 1 )N(O) 2 S, (R 5 O) 2 (O)P, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, (R 1 O)(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S(R 1 )N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, R 1 (O)CO—(C 1 -C 6 )-alkyl, R 2 (O) 2 SO—(C 1 -C 6 )-alkyl, R 2 O(O)CO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)CO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N(O) 2 S—(C 1 -C 6 )-alkyl, (R 5 O) 2 (O)P—(C 1 -C 6 )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl-(C 1 -C 6 )-alkyl, where the six latter radicals are each substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

W is hydrogen, halogen, nitro, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl, halo-(C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl-(O) n S—, (C 1 -C 6 )-haloalkyl-(O) n S—, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 4 )-haloalkyl, R 1 (O)C, R 1 (R 1 ON═)C, R 1 O(O)C, (R 1 ) 2 N, R 1 (O)C(R 1 )N or R 2 (O) 2 S(R 1 )N,

R and R′ are each independently (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, phenyl, heteroaryl or heterocyclyl, where the three latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

or R and R′ together with the sulfur atom to which they are bonded form a 3- to 8-membered unsaturated, semisaturated or saturated ring which contains, apart from the carbon atoms and apart from the sulfur atom of the sulfoximino group, in each case m ring members selected from the group consisting of N(R 1 ), O and S(O) n , and where this ring in each case is substituted by s radicals from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where this ring bears n oxo groups,

R″ is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, R 1 (O)CO—(C 1 -C 6 )-alkyl, R 2 (O) 2 SO—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 O(O)C(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 2 (O) 2 S, or benzyl substituted in each case by s radicals selected from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen,

R Y is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy, (C 2 -C 6 )-alkenyloxy, (C 2 -C 6 )-alkynyloxy, cyano, nitro, methylsulfanyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl each substituted by s radicals selected from the group consisting of (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy, halo-(C 1 -C 6 )-alkoxy and halogen, and where heterocyclyl bears n oxo groups,

R 1 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 -cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 ) -alkyl, phenyl-N(R 3 )—(C 1 -C 6 )-alkyl, heteroaryl-N(R 3 )—(C 1 -C 6 )-alkyl, heterocyclyl-N(R 3 )—(C 1 -C 6 )-alkyl, phenyl-S(O) n —(C 1 -C 6 )-alkyl, heteroaryl-S(O) n —(C 1 -C 6 )-alkyl, heterocyclyl-S(O) n —(C 1 -C 6 )-alkyl, where the fifteen latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O(O) 2 S, (R 3 ) 2 N(O) 2 S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

R 2 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, halo-(C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, halo-(C 3 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkenyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 ) -alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 )-alkyl, phenyl-N(R 3 )—(C 1 -C 6 )-alkyl, heteroaryl-N(R 3 )—(C 1 -C 6 )-alkyl, heterocyclyl-N(R 3 )—(C 1 -C 6 )-alkyl, phenyl-S(O) n —(C 1 -C 6 )-alkyl, heteroaryl-S(O) n —(C 1 -C 6 )-alkyl, heterocyclyl-S(O) n —(C 1 -C 6 )-alkyl, where the fifteen latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 -alkyl, (C 3 -C 6 )-cycloalkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S, R 3 O(O) 2 S, (R 3 ) 2 N(O) 2 S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

R 3 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl,

R 4 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl or phenyl,

R 5 is hydrogen or (C 1 -C 4 )-alkyl,

R 7 is acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, or (C 3 -C 6 )-cycloalkyl, or is heteroaryl or heterocyclyl each of which is substituted by s radicals selected from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen,

n is 0, 1 or 2,

m is 0, 1, 2, 3 or 4,

s is 0, 1, 2 or 3.

2. A sulfinylaminobenzamide and/or salt thereof as claimed in claim 1 , in which

Q is a Q3 radical,

X is nitro, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 (R 1 ON═)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 1 (O)C(R 1 )N, R 2 (O) 2 S(R 1 )N, R 2 O(O)C(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S, (R 5 O) 2 (O)P, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, (R 5 O) 2 (O)P—(C 1 -C 6 )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl-(C 1 -C 6 )-alkyl, where the six latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

Z is hydrogen, nitro, halogen, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, R 1 (O)C, R 1 (R 1 ON═)C, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 1 (O)C(R 1 )N, R 2 (O) 2 S(R 1 )N, R 2 O(O)O(R 1 )N, (R 1 ) 2 N(O)C(R 1 )N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S, (R 5 O) 2 (O)P, R 1 (O)C—(C 1 -C 6 )-alkyl, R 1 O(O)C—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C—(C 1 -C 6 )-alkyl, NC—(C 1 -C 6 )-alkyl, R 1 O—(C 1 -C 6 )-alkyl, (R 1 ) 2 N—(C 1 -C 6 )-alkyl, R 1 (O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) 2 S(R 1 )N—(C 1 -C 6 )-alkyl, R 2 O(O)C(R 1 )N—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O)C(R 1 )N—(C 1 -C 6 )-alkyl, R 2 (O) n S—(C 1 -C 6 )-alkyl, R 1 O(O) 2 S—(C 1 -C 6 )-alkyl, (R 1 ) 2 N(O) 2 S—(C 1 -C 6 )-alkyl, (R 5 O) 2 (O)P—(C 1 -C 6 )-alkyl, phenyl, heteroaryl, heterocyclyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl -(C 1 -C 6 )-alkyl, where the six latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, cyano, thiocyanato, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

W is hydrogen, halogen, nitro, cyano, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkyl-(O) n S—, R 1 O(O)C, (R 1 ) 2 N, R 1 (O)C(R 1 )N or R 2 (O) 2 S(R 1 )N,

R and R′ are each independently (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, halo-(C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, phenyl, heteroaryl or heterocyclyl, where the three latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S and R 1 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

or R and R′ together with the sulfur atom to which they are bonded form a 3- to 8-membered unsaturated, semisaturated or saturated ring which contains, apart from the carbon atoms and apart from the sulfur atom of the sulfoximino group, in each case m ring members from the group consisting of N(R 1 ), O and S(O) n , and where this ring in each case is substituted by s radicals from the group consisting of halogen, (C 1 -C 6 ) -alkyl, halo-(C 1 -C 6 )-alkyl, R 1 O(O)C, (R 1 ) 2 N(O)C, R 1 O, (R 1 ) 2 N, R 2 (O) n S, R 1 O(O) 2 S, (R 1 ) 2 N(O) 2 S and R 1 O—(C 1 -C 6 )-alkyl, and where this ring bears n oxo groups,

R″ is hydrogen,

R Y is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 7 )-cycloalkyl, (C 1 -C 6 )-alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino, aminocarbonyl or methoxymethyl,

R 1 is hydrogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 )-alkyl, where the nine latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

R 2 is (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, halo-(C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, cycloalkyl-(C 1 -C 6 )-alkyl-O—(C 1 -C 6 )-alkyl, phenyl, phenyl-(C 1 -C 6 )-alkyl, heteroaryl, heteroaryl-(C 1 -C 6 )-alkyl, heterocyclyl, heterocyclyl-(C 1 -C 6 )-alkyl, phenyl-O—(C 1 -C 6 )-alkyl, heteroaryl-O—(C 1 -C 6 )-alkyl, heterocyclyl-O—(C 1 -C 6 )-alkyl, where the nine latter radicals are each substituted by s radicals selected from the group consisting of nitro, halogen, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 ) -alkyl, R 3 O(O)C, (R 3 ) 2 N(O)C, R 3 O, (R 3 ) 2 N, R 4 (O) n S and R 3 O—(C 1 -C 6 )-alkyl, and where heterocyclyl bears n oxo groups,

R 3 is hydrogen or (C 1 -C 6 )-alkyl,

R 4 is (C 1 -C 6 )-alkyl,

R 5 is hydrogen or (C 1 -C 4 )-alkyl,

R 7 is acetoxy, acetamido, methoxycarbonyl or (C 3 -C 6 )-cycloalkyl,

n is 0, 1 or 2,

m is 0, 1 or 2,

s is 0, 1, 2 or 3.

3. A sulfinylaminobenzamide and/or salt as claimed in claim 1 , in which

Q is a Q3 radical,

X is nitro, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl,

Z is hydrogen, nitro, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, hydroxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxy, ethoxy, methylsulfanyl, methylsulfinyl or methylsulfonyl,

W is hydrogen, chlorine or methyl,

R and R′ are each independently methyl, ethyl or n-propyl,

or

R and R′ together with the sulfur atom to which they are bonded form a 5- or 6-membered ring which, apart from the carbon atoms and apart from the sulfur atom of the sulfoximino group, contains m oxygen atoms,

R″ is hydrogen,

R Y is methyl, ethyl, n-propyl, chlorine or amino, and

m is 0 or 1.

4. A herbicidal composition, comprising a herbicidally active content of at least one compound of the formula (I) and/or salt as claimed in claim 1 .

5. The herbicidal composition as claimed in claim 4 in a mixture with one or more formulation auxiliaries.

6. The herbicidal composition as claimed in claim 4 , comprising at least one further pesticidally active substance selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

7. The herbicidal composition as claimed in claim 6 , comprising a safener.

8. The herbicidal composition as claimed in claim 7 , comprising cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.

9. The herbicidal composition as claimed in claim 6 , comprising a further herbicide.

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

11. A method of controlling unwanted plants comprising applying a compound of formula (I) and/or salt as claimed in claim 1 to one or more unwanted plants.

12. A method of controlling unwanted plants as claimed in claim 11 comprising applying a compound of formula (I) and/or salt as claimed in claim 1 to one or more unwanted plants in the presence of one or more crops of useful plants.

13. A method of controlling unwanted plants as claimed in claim 12 wherein the useful plants are transgenic useful plants.

14. A sulfinylaminobenzamide and/or salt as claimed in claim 1 , in which

Q is a Q3 radical,

X is halogen,

Z is halogen,

W is hydrogen,

R and R′ are each independently (C 1 -C 6 )-alkyl, or R and R′ together with the sulfur atom to which they are bonded form a 6-membered ring which, apart from the carbon atoms and apart from the sulfur atom of the sulfoximino group, contains m oxygen atoms,

R″ is hydrogen,

R Y is (C 1 -C 6 )-alkyl, and

m is 0 or 1.

15. A sulfinylaminobenzamide as claimed in claim 1 of the formula

and/or a salt thereof.

16. A sulfinylaminobenzamide as claimed in claim 1 of the formula

and/or a salt thereof.

17. A sulfinylaminobenzamide as claimed in claim 1 of the formula

and/or a salt thereof.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Jul 4, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER CROPSCIENCE AKTIENGESELLSCHAFT
Reel/Frame 064198/0823 →
CHANGE OF ADDRESS Recorded Jun 12, 2023
From: BAYER INTELLECTUAL PROPERTY GMBH
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 064021/0344 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 10, 2014
From: AHRENS, HARTMUT; BRAUN, RALF; KOEHN, ARNIM; LEHR, STEFAN; DIETRICH, HANSJOERG; SCHMUTZLER, DIRK; GATZWEILER, ELMAR; ROSINGER, CHRISTOPHER HUGH
To: BAYER INTELLECTUAL PROPERTY GMBH
Reel/Frame 034133/0458 →