TW201339131A - Herbicidally active sulfinimidoyl-and sulfonimidoylbenzoyl derivatives - Google Patents

Abstract

Sulfinimidoyl-and sulfonimidoylbenzoyl derivatives of the formula (I) are described as herbicides. In this formula (I), 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 cyclohexanedionyl, pyrazolyl or isoxazolyl radical.

Description

Herbicidal sulfinimide- and sulfonimidobenzamide derivatives

The present invention relates to the technical field of herbicides, in particular to herbicides for the selective control of broadleaf and weeds in useful crops.

WO 03/014071 A1 and WO 2011/012247 A1 disclose herbicidal benzepidine cyclohexanediones having an alkyl oxysulfoxide group, an alkyl sulfinium ring at the 3-position of the phenyl ring. Or alkylsulfonyl. Herbicidal benzionylpyrazole having an alkyl oxysulfoxide, alkylsulfinyl or alkylsulfonyl group at the 3-position of the phenyl ring is from WO 2008/125214 A1 and WO 2009/ Known in 149806 A2. US 2011/0144345 A1 and WO 2004/052849 A1 each disclose a benzamidine derivative having a sulfonium imine group at the 3-position of the phenyl ring. However, the herbicidal activity and/or crop compatibility of the compounds mentioned in these documents are always insufficient.

It is an object of the present invention to provide herbicidal active compounds having improved properties over compounds known in the prior art.

It has been found that a benzamidine derivative having a sulfinium- or sulfonium-imino group at the 3-position of the phenyl ring is suitable as a herbicide.

Accordingly, the present invention provides a sulfinimido- and sulfonimidobenzamide derivative of the formula (I) or a salt thereof The definition of the code and index is as follows: Q is the group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, R ⁶ S, R ⁷ (R ⁸ ) N, R ^b , R ^c , R ^f and R ^g are each independently hydrogen or (C ₁ -C ₄ )-alkyl, and R ^d and R ^e are respectively Independently hydrogen or (C ₁ -C ₄ )-alkyl or a carbon atom attached thereto to form a carbonyl group, ^Rh is hydrogen, (C ₁ -C ₆ )-alkylsulfonyl, (C ₁ -C ₄ )-Alkoxy-(C ₁ -C ₆ )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzhydryl, benzhydryl-(C ₁ -C ₆ )-alkyl, benzyl, wherein the last five groups may be monosubstituted by halogen, (C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkoxy, if desired Or polysubstituted, R ⁱ is (C ₁ -C ₄ )-alkyl, R ^k is hydrogen, (C ₁ -C ₄ )-alkyl, (C ₃ -C ₇ )-cycloalkyl, A and Y are respectively Independently of oxygen, S(O) _n , N(R ³ ), carbonyl or (C ₁ -C ₄ )-alkylene, which is substituted by n R ⁹ groups and inserted into n selected from the following The elements in the group: oxygen, S(O) _n , N(R ³ ) and carbonyl, X is nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halogen - (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 )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkenyl, (C ₃ - C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkenyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkenyl-(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, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ The alkyl group, wherein the last six groups are respectively substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate, (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 wherein the heterocyclic group carries n pendant oxy groups, Z is hydrogen, nitro, halogen, cyano, thiocyanamido, (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 )-cycloalkenyl, halo-(C ₃ - C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆₎ - alkyl, (C ₃ -C ₆₎ - cycloalkenyl, - (C ₁ -C ₆₎ - alkyl , Halo - (C ₃ -C ₆₎ - cycloalkenyl, - (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, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆₎ - alkyl, heterocyclyl - (C ₁ -C ₆₎ - alkyl, where the last-mentioned 6 s-th groups each consisting of each group was selected from a group of substituents: nitro, halogen, cyano, thiocyanate acyl, (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 wherein the heterocyclic group There are n pendant oxy groups, W is hydrogen, halogen, nitro, cyano, thiocyanate, (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 is (C ₁ -C ₆ )-alkane group, (C ₂ -C ₆₎ - alkenyl or (C ₂ -C ₆₎ - alkynyl, respectively, each selected from a s-matter of the In the substituted groups: nitro, halogen, cyano, thiocyanate acyl, (C ₃ -C ₆₎ - ^{cycloalkyl, 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 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 S(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(R ¹ )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 C(O)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 and (R ⁵ O) ₂ (O)P, or (C ₃ -C ₆ )-ring Alkyl, (C ₃ -C ₆ )-cycloalkenyl, phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl , heterocyclic group, heterocyclic group-(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 ¹ )-(C ₁ -C ₆ )-alkyl, heteroaryl-N(R ¹ )- (C ₁ -C ₆ )-alkyl, hetero Cyclo-N(R ¹ )-(C ₁ -C ₆ )-alkyl, phenyl-S(O) _n -(C ₁ -C ₆ )-alkyl, heteroaryl-S(O) _n - (C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl, each cyclic moiety of which is composed of s selected from the following Group substitution in the group: nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, 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 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 S(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(R ¹ )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 C(O)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 and R ¹ O-(C ₁ -C ₆ )-alkyl, and wherein the heterocyclic group carries n pendant oxy groups, R' is hydrogen, nitro, halogen, cyanide a group, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-alkenyl, halo-(C ₃ -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 ² O(O)C, (R ¹ ) ₂ N(O)C, R ² S(O)C, (R ¹ ) ₂ N(S)C, R ¹ (R ¹ O) N(O)C, R ² (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 ) ₂ N, R ² (O) _n S, (R ² ) ₃ Si-(C ₁ -C ₆ )-alkyl-(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 ² (O) ₂ S(R ¹ )N(O) ₂ S, (R ⁵ O) ₂ (O)P, (R ² ) ₃ Si, 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 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, 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, m 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, (R ² ) ₃ Si-(C ₁ -C ₆ )-alkyl, phenyl, heteroaryl, heterocyclic, phenyl-(C ₁ -C ₆ )- Alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, of which the last 6 phenyl, heteroaryl and heterocyclic groups are mentioned The cyclic moiety is substituted by s groups selected from the group consisting of nitro, halogen, cyano, sulfur Acyl, (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 wherein the heterocyclic group bears n pendant oxy 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 )-alkyne , (C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkyl, (C ₃ -C ₆ )-cycloalkane -(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, cycloalkyl-(C ₁ -C ₆ )-alkane -O-(C ₁ -C ₆ )-alkyl, phenyl, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl, heteroaryl-(C ₁ -C ₆ )-alkyl , heterocyclic group, heterocyclic group-(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 )-alkane Base, heteroaryl-S(O) _n -(C ₁ -C ₆ )-alkyl, heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl, wherein the last 15 groups are respectively composed of s selected from the following groups Substituted in the group: nitro, halogen, cyano, thiocyanate, (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 wherein the heterocyclic group carries n pendant oxy groups, and 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₎ - Group, a phenyl group ^{-N (R 3) - (C} 1 -C 6) - alkyl, heteroaryl, ^{-N (R 3) - (C} 1 -C 6) - alkyl, a heterocyclic group -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, wherein the last 15 groups are respectively subjected to s groups selected from the group consisting of the following Group substitution: nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkane Base, 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 wherein the heterocyclic group carries n pendant oxy 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, and R ⁶ is (C ₁ - C ₄ )-alkyl or phenyl substituted by m groups selected from the group consisting of halogen, nitro, cyano, (C ₁ -C ₄ )-alkyl, C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-haloalkoxy, R ⁷ is hydrogen, (C ₁ -C ₄ )-alkane Or (C ₁ -C ₄ )-alkoxy, R ⁸ is hydrogen or (C ₁ -C ₄ )-alkyl, or R ⁷ and R ^{8 together} with the nitrogen atom to which they are attached form 5- or 6- a saturated, partially saturated or unsaturated ring further comprising n heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and substituted by m groups selected from the group consisting of halogens, Cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-haloalkoxy R ⁹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-halogen Alkoxy or (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, m is 0, 1, 2, 3, 4 or 5, n is 0, 1 or 2, s Is 0, 1, 2 or 3, and t is 0 or 1.

In the formula (I) and all of the formulas shown below, the alkyl group having more than 2 carbon atoms may be a straight chain or a branched chain. The alkyl group is, for example, methyl, ethyl, n- or isopropyl, n-, i-, tri- or 2-butyl, pentyl, hexyl (eg, n-hexyl, isohexyl, and 1,3- Dimethyl butyl). Similarly, an alkenyl group is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl , but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl. The alkynyl group is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-3-yn-1-yl. In each case, the multiple bond can be located anywhere in the unsaturated group. The cycloalkyl group is a carbon cyclic saturated ring system having 3 to 6 carbon atoms, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group or a cyclohexyl group. Similarly, the cycloalkenyl group has 3 to 6 A monocyclic alkenyl group of a carbocyclic group member, for example, a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, and a cyclohexenyl group, wherein the double bond may be located at any position.

Halogen is fluorine, chlorine, bromine or iodine.

A heterocyclic group is a saturated, partially saturated or fully unsaturated cyclic group containing from 3 to 6 ring atoms, wherein one to four ring atoms are selected from the group consisting of oxygen, nitrogen and sulfur and can be further combined with benzo Ring condensation. The heterocyclic group is, for example, piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl or oxetane. The heteroaryl group is an aromatic cyclic group containing 3 to 6 ring atoms, wherein 1 to 4 ring atoms are selected from the group consisting of oxygen, nitrogen and sulfur and can be further condensed with a benzo ring. Heteroaryl is, for example, benzimidazol-2-yl, furyl, imidazolyl, iso Azyl, isothiazolyl, Azolyl, pyridyl Base, pyrimidinyl, oxime Base, pyridyl, benzo Azyl, thiazolyl, pyrrolyl, pyrazolyl, thienyl, 1,2,3- Diazolyl, 1,2,4- Diazolyl, 1, 2, 5- Diazolyl, 1,3,4- Diazolyl, 1,2,4-triazolyl, 1,2,3-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4- Triazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-thiadiazolyl, 1,2,5-thiadiazolyl, 2H- 1,2,3,4-tetrazolyl, 1H-1,2,3,4-tetrazolyl, 1,2,3,4- Triazolyl, 1, 2, 3, 5- Triazolyl, 1,2,3,4-thiatriazolyl and 1,2,3,5-thiatriazole. If a group is substituted with a plurality of substituents, it is meant to be substituted by one or more of the same or different groups described above. This also applies to ring systems composed of different atoms and elements. At this time, those skilled in the relevant art know that their compounds which are unstable under standard temperature and pressure conditions are not within the scope of patent application.

Depending on the nature of the compound of formula (I) and the attached substituents, stereoisomers may occur in the compounds of formula (I). If, for example, one or more asymmetrically substituted carbon atoms are present, they may be enantiomers and diastereomers. Stereoisomers also occur when n in the S(O) _n group is 1 (anthracene). Further, the sulfur atom of the sulfoximine or sulfoximine group is the center of the palm. A stereoisomer can be obtained from a mixture obtained by the conventional method by a conventional separation method such as a chromatographic separation method. It is also possible to selectively react to prepare stereoisomers using optically active starting materials and/or adjuvants. The invention is also related to all stereoisomers of formula (I), but not all of which are not explicitly shown, and mixtures thereof.

The compounds of formula (I) can form salts. The salt formation method can utilize a base to act on the compound of the formula (I) having an acidic hydrogen atom (for example, when Ra is ^a hydroxyl group or ^Rh is hydrogen). Suitable bases are, for example, organic amines such as trialkylamines, morpholines, piperidines or pyridines, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and hydrogencarbonates, in particular sodium hydroxide With potassium hydroxide, sodium carbonate and potassium carbonate, and sodium hydrogencarbonate and potassium hydrogencarbonate. Such salts are compounds in which acidic hydrogen is replaced by agriculturally applicable cations, such as metal salts, in particular alkali metal or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts. a salt or a quaternary ammonium salt formed with an organic amine, for example: with the formula [NRR*R**R***] ⁺ (wherein R, R*, R** and R*** are independently represented a salt formed by a cation of an organic group, specifically an alkyl group, an aryl group, an arylalkyl group or an alkylaryl group. Also suitable are alkyl hydrazines and alkyl cerium oxide salts such as (C ₁ -C ₄ )-trialkyl hydrazine and (C ₁ -C ₄ )-trialkyl cerium oxide salts.

The compound of formula (I) may be substituted with a suitable basic or organic acid (for example, an amine group, an alkylamino group, a dialkylamino group, a piperidinyl group, a morpholinyl group or a pyridyl group) (for example). : mineral acids such as: HCl, HBr, H ₂ SO ₄ , H ₃ PO ₄ or HNO ₃ or organic acids such as carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulphur An acid such as p-toluenesulfonic acid forms an adduct to form a salt. At this time, the salt contains an conjugate base of an acid as an anion.

Preferably, in the compound of formula (I), Q is a group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, and R ^b , R ^c , R ^f and R ^g are each independently hydrogen or (C ₁ -C ₄ )-alkyl, and R ^d and R ^e are each independently hydrogen or (C ₁ -C ₄ )- An alkyl group or a carbon atom to which it is attached forms a carbonyl group, ^Rh is hydrogen, R ⁱ is (C ₁ -C ₄ )-alkyl, R ^k is hydrogen, (C ₁ -C ₄ )-alkyl, C ₃ -C ₇ )-cycloalkyl, A and Y are each independently oxygen or (C ₁ -C ₄ )-alkylene, which is substituted by n R ⁹ groups, X is nitro, halogen, cyanide , (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, hetero Aryl, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl , wherein the last six groups are substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkane , 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 wherein the heterocyclic group bears n pendant oxy 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 )-cycloalkane , 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, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )- The alkyl group, wherein the last six groups are respectively substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate , (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 wherein the heterocyclic group carries n pendant oxy 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 is (C ₁ -C ₆ )-alkyl, which is substituted by s groups selected from the group consisting of halogen, cyano, (C _{3 )} -C ₆ )-cycloalkyl, R ¹ (O)C, R ¹ (R ¹ ON=)C, R ¹ O(O)C, (R ¹ ) ₂ N(O)C, R ² (O) ₂ S(R ¹ )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 ¹ (O)C(R ¹ )N(O) ₂ S, R ² O(O)C(R ¹ )N(O) ₂ S and (R ¹ ) ₂ N(O) C(R ¹ )N(O) ₂ S or (C ₃ -C ₆ )-cycloalkyl, which is substituted by s groups selected from the group consisting of halogens, (C ₁ -C ₆ )-alkyl, halogen-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, R ¹ O(O)C and (R ¹ ) ₂ N(O)C, R' is hydrogen, nitro, cyano, (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, R ¹ (O)C, R ² O(O)C, (R ¹ ) ₂ N(O)C, R ² (O) ₂ S, 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-(C ₁ -C ₆ )-alkyl, (R ¹ ) ₂ N-(C ₁ -C ₆ )-alkyl, R ² (O) _n S-(C ₁ -C ₆ )-alkyl, 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, heterocyclic, 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, The 9 groups mentioned in the last are substituted by s groups selected from the group consisting of nitro, halogen, (C ₁ -C ₆ )-alkyl, halogen-(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 wherein the heterocyclic group bears n pendant oxy 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, benzene , 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 ) - an alkyl group, wherein the last 9 groups are respectively substituted by s groups selected from the group consisting of nitro, halogen, (C ₁ -C ₆ )-alkyl, halogen-( 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, Wherein heterocyclic group with n oxo, 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 ⁹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-haloalkoxy or (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, n is 0, 1 or 2, and s is 0, 1, 2 or 3 , t is 0 or 1. Particularly preferably, in the compound of formula (I), Q is a group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, R ^b , R ^c , R ^f and R ^g are each independently hydrogen or a methyl group, R ^d , R ^e are hydrogen or a carbon atom attached thereto forms a carbonyl group, and ^Rh is hydrogen, R ⁱ Is methyl or ethyl, R ^k is hydrogen, methyl or cyclopropyl, A and Y are each independently CH ₂ or CH ₂ CH ₂ , X is nitro, halogen, methyl, ethyl, n-propyl, Isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, Ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, Methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Z is hydrogen, nitro, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, tri Fluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, A Alkylsulfanyl, methylsulfinyl or methylsulfonyl, W is hydrogen, chlorine or methyl, R is methyl, ethyl N-propyl, R 'is hydrogen or cyano group, t is 0 or 1.

The compounds of formula (I) according to the invention can be prepared from the corresponding formula (I-thioether) thioethers (reaction Figure 1). Thus, the thioether is converted using the cyanamide and the oxidizing agent (oxyiodobenzene diacetate, sodium hypochlorite or N-bromosuccinimide) to form the corresponding sulfoximine, which is reoxidized to the sulfoximine. The oxidizing agent suitable for the oxidation to form the sulfoximine is, for example, m-chloroperbenzoic acid, sodium permanganate, or a mixture of sodium periodate and antimony trichloride. For example, NH-sulphonimine can be prepared from sodium azide using sodium azide and sulfuric acid, and reagents such as, for example, cyanogen bromide, decyl chloride or anhydride, chloroformate, nitric acid or other compounds can be used. Functionalized with a nitrogen atom. The oxidation of the N-sulfonated sulfinimide to the corresponding sulfonimide can be carried out using, for example, hydrogen. Alternatively, the hydrazine can be converted to N-thiolated or N-sulfonated sulfonimide. The carboxamide or sulfonamide can be re-cleaved separately to form NH-sulfonimide. The synthesis of sulfoximine and sulfonimide from thioether or the synthesis of sulfonimide from hydrazine, or the derivatization of sulfoximine and sulfonimide (also referred to as NH-sulfonate) The method of quinone imine) is specifically described, for example, in Bolm, C. Org. Lett. 2004, 6, 1305; Bolm, C. Org. Lett. 2007, 9, 3809; Bolm, C. Synthesis 2010, 17, 2922; Bolm, C. Adv. Synth. Catal. 2010, 352, 309; WO 2007/095229 A1, WO 2008/141843 A1, WO 2008/097235 A1, US 2008/0207910 A1, US 2008/0194634 A1 and US 2010/0056534 A1.

If necessary, it is necessary to use a protecting group in these synthetic sequences to achieve sufficient selectivity. In particular, the functionalization of NH-sulfonimide will in principle compete with similar functionalization on the guanamine nitrogen atom. The most appropriate process will depend on the type of substitution that is relevant.

The compounds of the formula (I-thioether) and the compounds of the formula (I-Athene) are known and described, for example, in WO 2003/014071 A1, WO 2008/125214 A1, WO 2009/149806 A1, WO 2011012247 A1, WO 2011012247 A1, EP 0 609 798 A1 and EP 0 625 508 A1.

It may be appropriate to change the sequence of reaction steps. Sulfonimide and, in particular, sulfinimide have insufficient stability under certain conditions (Bolm, C. Adv. Synth. Catal. 2010, 352, 309), so it may be appropriate to first synthesize benzamidine in the thioether phase. A base derivative (as shown in Figure 1) and produces sulfinimide or sulfonimide from the thioether only at the end of the synthesis process. However, if it has sufficient stability, depending on the substitution type, it may be preferable to first in the benzoic acid stage (or even in the earlier stage). Paragraph) The production of sulfinimide or sulfonimide from thioether, followed by conversion of only benzoic acid to form its benzamidine derivative (reaction Figure 2). A conversion process for the formation of a plurality of benzamidine derivatives of a structure which does not comprise a sulfinimide group or a sulfonimide group from benzoic acid is known and described, for example, in WO 2003/014071 A1, WO 2008/125214 A1, WO 2009/149806 A1, WO 2011012247 A1, WO 2011012247 A1, EP 0 609 798 A1 and EP 0 625 508 A1. Depending on the type of substitution, it may be appropriate to employ such a route to form a compound of formula (I) according to the invention.

In some instances, it may be appropriate to use a derivative of benzoic acid instead of free benzoic acid to carry out the reaction. Sometimes the stability of the functional group is only sufficient to operate in an acidic or basic medium, i.e., only free benzoic acid or only salts thereof may be used. Sometimes it is suitable to use esters such as methyl or ethyl esters. Usually, the third butyl ester is sufficient to stereoscopically mask the carboxyl group against the nucleophilic reagent, and it is easily cleaved in an acidic medium (TW Greene, PGM Wuts, "Protective Groups in Organic Synthesis", 2nd edition, John Wiley & Sons, Inc. 1991, p. 227 ff.). It is also suitable to use a group which is more stable than the carboxyl group, but it should also be easily converted back to the free carboxylic acid. Such groups include, for example: Orthochrome (TW Greene, PGM Wuts, "Protective Groups in Organic Synthesis", 2nd ed., John Wiley & Sons, Inc. 1991, p. 265 ff.; Z. Hell et al. Tetrahedron Letters 43 (2002), 3985-3987).

The benzoic acid of the above formulas (IIa) and (IIb) and its ethyl ester, methyl ester and benzhydryl chloride are novel and represented by the formula (II).

In the formula (II), Q* is a hydroxyl group, an ethoxy group, a methoxy group or a chlorine group. R, R', X, W, Z and t have the definition of formula (I). The compounds of the formula (II) are particularly suitable for the preparation of the compounds of the formula (I) according to the invention. The compounds of formula (II) also form part of the subject matter of the present invention.

The operation of each reaction mixture is usually carried out by a known method such as a crystallization method, an aqueous extraction operation method, a chromatography method or a combination of these methods.

The collection of the compound of the formula (I) and/or its salts which can be synthesized according to the above reaction can also be prepared in a parallel manner, which can be carried out manually or completely automatically. At this point, it may be possible, for example, to automate the reaction process, the process or the purification of the product or intermediate. In summary, this process can be obtained, for example, from D. Tiebes in "Combination Chemistry - Synthesis, Analysis, Screening (Combinatorial) Understanding the explanation in Chemistry-Synthesis, Analysis, Screening (edited by Günther Jung, Wiley 1999, pages 1 to 34).

There are many commercially available equipment for parallel reaction processes and operations, such as: Calpyso reaction blocks (from Barnstead International, Dubuque, Iowa 52004-0797, USA), or reaction stations (from Radleys, Shirehill, Saffron). Walden, Essex, CB 11 3AZ, UK) or MultiPROBE Automated Workstations (from Perkin Elmar, Waltham, Massachusetts 02451, USA). Purification of the compounds of formula (I) and their salts or intermediates produced during the preparation can be carried out in parallel using chromatographic equipment (for example: from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA).

In the above-mentioned modular process, each round of the program is automated, but each round must be manually performed. This does not require the use of a partially or fully integrated automation system with associated automatic modules operated by, for example, automated tools. Such automated systems are available, for example, from Caliper, Hopkinton, MA 01748, USA.

The effectiveness of individual or several synthetic steps can be achieved by utilizing a polymer-supported reagent/scavenger resin. This professional literature describes a series of experimental procedures, for example: ChemFiles, Vol. 4, No. 1, "Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis ) (Sigma-Aldrich).

In addition to the methods described herein, the compounds of formula (I) and salts thereof can be prepared, in whole or in part, by solid phase support. For this purpose, the synthesis or the individual intermediates or all intermediates of the synthesis of the relevant processes are combined on the synthetic resin. The solid phase support synthesis method has been described in detail in the professional literature, for example: Barry A. Bunin's "The Combinatorial Index", Academic Press, 1998 and "Combined Chemistry-Synthesis, Analysis, Screening (Combinatorial Chemistry-Synthesis, Analysis, Screening (Günther Jung, ed.), Wiley 1999". A series of solid-phase support synthesis methods can be used in the literature. Known methods can also be carried out manually or automatically. For example, the reaction can be carried out in a microreactor from Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA using IRORI technology.

The individual or several synthetic steps carried out in the solid phase and in the liquid phase can be carried out by means of microwave technology. A series of experimental methods have been described in the professional literature, for example: "Microwaves in Organic and Medicinal Chemistry" (edited by C. O. Kappe and A. Stadler, Wiley, 2005).

Compounds of formula (I) and salts thereof, which are referred to as pools, can be prepared according to the procedures described herein. The invention also relates to a collection library comprising at least two compounds of the formula (I) and salts thereof.

The compound of the formula (I) (and/or its salts) according to the invention (hereinafter collectively referred to as "the compound according to the invention") has excellent herbicidal activity against a broad-spectrum monocotyledonous and dicotyledonous annual harmful plant which affects economic importance. . These active substances are also effective against perennial harmful plants that grow out of the roots, primary roots or other perennial organs and are difficult to control.

The invention therefore also relates to a method of controlling unwanted plants or regulating plant growth, preferably crops, wherein one or more compounds (groups) according to the invention are applied to plants (for example: harmful plants, such as monocotyledons or dicotyledons) Weeds or unwanted crop plants), seeds (eg grain, seeds or vegetative propagation plants such as: tubers or young shoots with buds) or areas where plants are grown (eg planting areas). Herein, the compound according to the invention can be, for example, before planting (if suitable It can also be mixed into the soil, applied before or after excavation. The individual representative examples of monocotyledonous and dicotyledonous weed populations which may be controlled by the compounds according to the invention may be mentioned below (but are not intended to limit certain varieties).

Monocotyledonous harmful plant genus: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Finch Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Apis (Ischaemum), Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Teeth Poa), Rottboellia, Sagittaria, Scripus, Setaria, Sorghum.

Dicotyledonous weeds: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia ), Atriplex, Bearis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, 蓟(Cirsium), Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Corn Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Welded Vegetables Rorippa), Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum , Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Amaranth (Viola), Xanthium.

If the compound according to the invention is applied to the soil surface prior to germination, the weed seedlings can be completely prevented from being exhumed or prevented from growing until they reach the cotyledon stage, but then the growth can be prevented, and the death is complete after 3 to 4 weeks. .

When the active substance is applied to the green plant after excavation, that is, the growth is stopped after the treatment, the harmful plant stays in the growth stage at the time of application or completely dies after a period of time, so that it is possible to eliminate the disadvantage of the crop plant early and continuously. Weed competition.

Although the compounds according to the invention exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, economically important crops, for example: dicotyledonous crops: Arachis, Beta, Brassica , Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Tomato (Lycopersicon) ), Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or Monocotyledonous genus: Allium, Ananas, Asparagus, Uganda Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum (Sorghum), Triticale, Triticum, Zea (Zea) and Wheat (Triticum) are only insignificant or completely harmless. It depends on the structure and application rate of each compound according to the present invention. The compounds of the present invention are highly suitable for the selective control of the growth of unwanted plants in crops such as agriculturally useful crops or ornamental plants.

Furthermore, the compounds according to the invention (depending on their structure and application rate) have excellent growth regulating properties for crop plants. It participates in the metabolism of plants in a regulated manner and can therefore be used to influence plant composition in a targeted manner and to facilitate harvesting, such as, for example, initiating dehydration and hindering growth. In addition, it is also suitable for general control and suppression of unwanted vegetative growth without destroying plants in the process. The practice of inhibiting vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops because, for example, it is possible to reduce or completely prevent lodging.

Active substances can also be used to control harmful plants in genetically modified crops or plants modified by conventional mutagenesis based on their herbicidal and modulating plant growth properties. In general, genetically modified plants are characterized by particularly advantageous properties, such as resistance to certain pesticides (primarily for certain herbicides), to plant diseases or to organisms that cause plant diseases (eg certain insects or microorganisms) Resistance to, for example, fungi, bacteria or viruses. Other special properties relate to, for example, the yield, quality, storage, composition and specific composition of the harvested material. Thus, transgenic plants having an increased starch content or modified starch quality or those having a harvested material having different fatty acid acid compositions are known.

The compound according to the present invention or a salt thereof is preferably used for the transfer of genetically important plants and ornamental plants of economically important crops, such as cereals such as wheat, barley, rye, oats, sorghum, and millet, rice. , cassava and corn, or crops such as beets, cotton, soybeans, canola, potatoes, tomatoes, peas, and other vegetables. The compound according to the invention is preferably used as a herbicide for It is a useful crop that is resistant to phytotoxic effects of herbicides or resistant to recombinant methods.

Common methods for producing novel plants having engineered properties compared to existing plants are, for example, conventional breeding methods and mutant strain formation methods. Alternatively, novel plants with engineered properties can be produced by means of recombinant methods (see for example: EP-A-0221044, EP-A-0131624). For example, several examples are described below: - Recombinant modification of crops designed to modify starches synthesized by plants (eg: WO 92/11376, WO 92/14827, WO 91/19806), - for certain snails (glufosinate) ) (see for example: EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or sulfonylureas (EP-A-0257993, US-A-5013659) Herbicide-resistant, transgenic crops, which can produce transgenic crops of Bacillus thuringiensis toxin (Bt toxin), such as cotton, which make plants resistant to certain pests (EP-A) -0142924, EP-A-0193259), - Transgenic crops with engineered fatty acid composition (WO 91/13972), - genes with novel components or secondary metabolites (eg novel plant defensins) Modification of crops, which increase disease resistance (EPA 309862, EPA0464461), genetically modified plants that reduce photorespiration and increase yield and stress resistance to stress (EPA 0305398), producing proteins of medical or diagnostic importance Transgenic crops ("molecular pharming"), - A genetically modified crop characterized by increased yield or improved quality, characterized by a combination of, for example, a genetically modified crop of the above novel nature ("multivalent transgenic crop").

Many molecular biotechnology systems for the production of novel transgenic plants with engineered properties are known in principle; see, for example: I. Potrykus and G. Spangenberg (ed.) "Gene Transfer to Plants" ), Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg. or Christou, "Trends in Plant Science" 1 (1996) 423-431).

In order to carry out this recombination method, it is possible to introduce a nucleic acid molecule into a plastid, and a mutagenesis method or a recombinant method using a DNA sequence can be used to engineer a sequence. For example, base substitution methods, removable partial sequences, or addition of natural or synthetic sequences by standard methods can be performed. In order to connect DNA fragments to each other, an aptamer or a linker can be added to the fragment; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd Edition, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, "Gene und Klone", VCH Weinheim 2nd Edition, 1996.

For example, the effect of co-suppression can be achieved by the expression of at least one corresponding antisense RNA, sense RNA, or by the performance of at least one correspondingly constructed ribozyme, which specifically cleaves the transcript of the above gene product, A plant cell having reduced gene product activity. It may be preceded by the use of a DNA molecule comprising all of the coding sequences of the gene product (including any flanking sequences that may be present) or a DNA molecule comprising only a portion of the coding sequence, the length of which is sufficient to produce in the cell. Antisense effect. It is also possible to use DNA sequences that are highly homologous, but not identical, to the coding sequence of the gene product.

When a nucleic acid molecule is expressed in a plant, the synthesized protein can be located in any interval of the plant cell. However, for positioning within a particular interval, for example, the coding region and DNA sequence can be ligated to ensure localization within a particular interval. this The sequence is known to those skilled in the relevant art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; and Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846 -850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in organelles of plant cells.

Transgenic gene cells can be regenerated using known techniques to produce whole plants. In principle, the transgenic plant can be any plant species, ie monocotyledonous or dicotyledonous.

Thus, the resulting transgenic plants have a transformation due to the overexpression, suppression or inhibition of homologous (=natural) genes or gene sequences or the results of heterologous (=foreign) genes or gene sequences. Nature characteristics.

The compounds according to the invention are preferably used in transgenic crops which are resistant to growth regulators (e.g., dicamba); or herbicides which inhibit plant essential enzymes (e.g., acetamidine lactide) Synthetase (ALS), EPSP synthase, branamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD); or from sulfonyl ureas, glyphosate, geranium (glufosinate) or benzamidine Herbicide herbicides, and similar active substances.

When the active substance according to the invention is used for the transfer of genetic crops, in addition to its effect on harmful plants, which can be observed in other crops, specific effects when applied to a particular transgenic crop are often observed, for example: Modification or specificization of expanded weed control, modified application rates, good combinability with herbicide-resistant transgenic crops, and effects on growth and yield of transgenic crops.

The invention therefore also relates to the use of a compound according to the invention as a herbicide for controlling harmful plants in a genetically modified crop.

The compound according to the invention may be in the form of a wettable powder, an emulsifiable concentrate, a spray Sprinkles, dust powders or granules are used in conventional preparations. The invention therefore also relates to herbicides and plant growth regulators comprising a compound according to the invention.

The compounds according to the invention may be formulated in a variety of different ways depending on the current biological and/or physio-chemical parameters. Examples of possible formulations are: wettable powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW) (eg, oil-in-water and oil-in-water emulsions). ), spray liquid, aqueous suspension (SC), oily or aqueous dispersion, oil miscible solution, capsule suspension (CS), dust powder (DP), seed dressing products, granules for spreading, and granules for soil, Particulate granules (GR), spray granules, coated granules and adsorbent granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and are described, for example, in "Chemische Technologie" by Winnacker-Küchler, Chemical Engineering, Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986; Wade van Valkenburg "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd edition, 1979, G. Goodwin Ltd. London.

The required adjuvants (eg, inert materials, surfactants, solvents, and other additives) are also known and described, for example, in Watkins' Handbook of Insecticide Dust Diluents. And Carriers)", 2nd Edition, Darland Books, Caldwell NJ, HvOlphen, "Introduction to Clay Colloid Chemistry"; 2nd Edition, J. Wiley & Sons, NY; C. Marsden" Solvent Guide (Solvents Guide); 2nd Edition, Interscience, NY 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley And Wood's "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schönfeldt's "Grenzflächenaktive Athylenoxidaddukte" [Ethylene Oxide Adduct Surfactant], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie" [Chemical Technology], Vol. 7, C. Hanser Verlag Munich, 4th edition, 1986.

Depending on the formulation, it may also be combined with other pesticidally active substances such as, for example, insecticides, acaricides, herbicides, fungicides and safeners, fertilizers and/or growth regulators, for example: Presented as a mixture or a large tank mixture. Suitable safeners are, for example, mefenpyr-diethyl, cyprosulfamide, diphenyl Isoxadifen-ethyl, cloquintocet-mexyl and dichlormid.

The wettable powder is a preparation which can be uniformly dispersed in water, and contains, in addition to the active material, an ionic and/or nonionic surfactant (wetting agent, dispersing agent), for example, in addition to a diluent or an inert substance. Also, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenes A phthalate, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium decylmethyltaurate. In order to prepare a wettable powder, the herbicidal active substance is taken, for example, uniformly finely ground in a conventional apparatus (for example, a hammer mill, a bowl mill, and a pneumatic jet mill), and mixed with the compounding agent simultaneously or sequentially.

The emulsifiable concentrate is prepared by dissolving the active substance in a solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or a high-boiling aromatic or hydrocarbon or adding one or more organic solvents. A mixture of ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium alkaryl sulfonates (eg calcium dodecylbenzene sulfonate) or nonionic emulsifiers (eg fats) Acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensates, alkyl polyethers, sorbitan esters (eg, for example : sorbitan fatty acid esters) or polyoxyethylene sorbitan esters (for example, polyoxyethylene sorbitan fatty acid esters).

The dust powder preparation method is a mixture of an active material and a finely divided solid material such as, for example, talc, mineral clay (e.g., kaolin, bentonite and pyrophyllite), or diatomaceous earth.

The aqueous suspension can be aqueous or oily. For example, it can be obtained by a wet milling method using a ball mill obtained from a product, and if necessary, adding a surfactant on the list (for example, as described in other formulation types).

The emulsion, for example, an oil-in-water emulsion (EW) can be produced, for example, by using a stirrer, a colloid mill and/or a static mixer, using an aqueous organic solvent, and adding a surfactant on the list if appropriate (for example: In the formulation type).

The granule preparation method may be sprayed on the adsorbent granular inert material by the active material, or the active material concentrate may be coated on the carrier by means of an adhesive (for example, polyvinyl alcohol, sodium polyacrylate or mineral oil) (for example: Sand, kaolin or granular inert material) on the surface. Suitable active materials can also be granulated according to conventional fertilizer granulation methods (if desired, with fertilizers).

Water-dispersible granules are usually produced by conventional methods such as spray drying, fluidized bed granulation, pan granulation, mixing with a high speed agitator, and extrusion without the use of solid inert materials. .

For the preparation of disc granules, fluidized bed granules, extruded granules and spray-dried granules, see, for example, "Spray-Drying Handbook", 3rd edition, 1979, G. Goodwin Ltd. , London; JEBrowning's "Agglomeration", Chemical and Engineering 1967, After the 147th page; "Perry's Chemical Engineer's Handbook", 5th edition, McGraw-Hill, New York 1973, p. 8-57.

Further details on formulations of crop protection products can be found, for example, in Gecklingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96. And J. Freyer, SAEvans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In general, the agrochemical preparation comprises from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of the compound according to the invention. In the wettable powder, the active substance concentration is, for example, about 10 to 90% by weight, and the balance is made up to 100% by weight from the conventional formulation. In the case of an emulsifiable concentrate, the active material concentration may range from about 1 to 90, preferably from 5 to 80% by weight. The dust powder formulation may comprise from 1 to 30% by weight of active material, most preferably from 5 to 20% by weight of active material, and the spray liquid comprises from about 0.05 to 80, preferably from 2 to 50% by weight. Compared to active substances. In the case of water-dispersible granules, the active substance content depends in part on the active compound in liquid or solid form, and depends on the granulation aid, filler, and the like employed. In the case of the water-dispersible granules, for example, the active material content is between 1 and 95% by weight, preferably between 10 and 80% by weight.

In addition, the above active substance formulation may include auxiliary agents commonly used in each case, such as: an adhesive, a humidifying agent, a dispersing agent, an emulsifier, a penetrating agent, a preservative, an antifreeze, a solvent, a filler, and the like. Agents, colorants, defoamers, evaporation inhibitors, and pH and viscosity modifiers.

According to these formulations, it can also be combined with other pesticide active substances (eg, For example: insecticides, acaricides, herbicides, fungicides, and compositions with safeners, fertilizers and/or growth regulators, for example, ready-to-use mixtures or large tank mixtures.

The active substance which can be combined with the compound according to the invention into a mixed formulation or a large tank mixture is, for example, inhibited, for example, acetamidine lactate synthase, acetyl-CoA carboxylase, cellulose synthase, quinone enolate Oxalic acid-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoen desaturase, photosystem I, photosystem II, protoporphyrin Known active substances of pro-oxidase are described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 14th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003. And the literature extracted from it. Known herbicides or plant growth regulators which may be combined with the compounds according to the invention are, for example, the following active substances (according to the common name of the International Organization for Standardization (ISO) or a chemically named compound, if appropriate And cooperate with the production of the code), and always include all application forms, such as: acids, salts, esters and isomers, such as: stereoisomers and optical isomers.

When a formulation in a commercial form is used, it may be diluted in a conventional manner as appropriate, for example, a wettable powder, an emulsifiable concentrate, a dispersant, and a water-dispersible granule are diluted with water. Formulations in the form of dusting powders, soil granules, granules and sprays are usually not diluted with other inert materials prior to application.

The rate of application of the compound of formula (I) required will vary with external conditions such as temperature, humidity, herbicidal properties employed, and the like. It can vary within a wide range of limitations, for example between 0.001 and 1.0 kg/ha and higher, but preferably between 0.005 and 750 g/ha.

The following examples illustrate the invention. A. Chemistry example 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimido)-2-methoxy-4-(trifluoromethyl)benzene Synthesis of thiol]pyrazole (example number 4-160 in the table) Step 1: Synthesis of 3-(N-cyano-S-methylsulfonimido)-2-methoxy-4-(trifluoromethyl)benzoic acid (Example No. 15-28 in the table)

3.71 g (33.1 mmol) of potassium t-butoxide was added to 250 ml containing 4.00 g (15.0 mmol) of 2-methoxy-3-(methylsulfanyl)-4-(trifluoromethyl)benzoic acid. In methanol. The mixture was stirred for 10 minutes, then 1.07 g (25.5 mmol) of cyanopyramine and 4.81 g (27.0 mmol) of N-bromosuccinimide were added sequentially. The reaction contents were stirred at room temperature for 2 hours. The solvent was then evaporated on a rotary evaporator and the residue was dissolved in a mixture of 120 ml of acetonitrile and water. 7.21 g (45.1 mmol) of sodium permanganate monohydrate was added, and the mixture was stirred at room temperature for one week. During this period, 3.6 g (22.5 mmol) of sodium permanganate monohydrate was added after one day and one day later. In operation, a 10% by weight sodium hydrogen sulfate solution was added. On a rotary evaporator, the solvent is substantially excluded at temperatures up to 30 °C. After the residue was cooled in an ice bath, it was acidified with 1 M hydrochloric acid. It was extracted 3 times with ice-cold dichloromethane. The solvent in the combined organic phase was removed on a rotary evaporator and the residue was purified by chromatography to yield 1.30 g.

Step 2: 5-Hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonimido)-2-methoxy-4-(trifluoromethyl) Synthesis of benzhydryl]pyrazole

First add 165 mg (75% by weight; 0.384 mmol) of 3-(N-cyano-S-methylsulfonate) Imino)-2-methoxy-4-(trifluoromethyl)benzoic acid and 68.9 mg (0.614 mmol) of 5-hydroxy-1,3-dimethylpyrazole to 20 ml of dichloromethane, added 128 mg (0.666 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. The mixture was stirred at room temperature for 16 hours, and was washed with 1M hydrochloric acid. After phase separation, the organic phase was dehydrated, filtered and the solvent was removed on a rotary evaporator. The residue was purified by chromatography and the obtained intermediate was dissolved in 15 ml of acetonitrile. 104 mg (1.02 mmol) of triethylamine, 8 drops of trimethyl cyanide and a tip of potassium cyanide were added. The mixture was stirred at room temperature for 16 hours, and the solvent was removed during the operation. The residue was dissolved in dichloromethane and washed with 3 mL 1M hydrochloric acid. After phase separation, the solvent of the organic phase is excluded, and the residue is purified by chromatography to give 31.3 mg of 5-hydroxy-1,3-dimethyl-4-[3-(N-cyano-S-methylsulfonate). Imino)-2-methoxy-4-(trifluoromethyl)benzylidene]pyrazole, purity 85% by weight. The examples listed in the table below were prepared analogously to the methods described above or similar to the methods described above. Such compounds are extremely preferred. The abbreviations used are as follows: Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl

Table 3a: A compound of formula (I) according to the invention wherein Q is Q3, R ⁱ is ethyl, and R ^h , R ^k and W are respectively hydrogen, t=1, and other groups are as defined in the table

Table 6: Compounds of formula (I) according to the invention, wherein Q is Q5, W is hydrogen, t=1, and other groups are as defined in the table

Table 9: Compounds of formula (I) according to the invention wherein Q is Q2, R ^a is hydroxy, R ^b , R ^f and W are respectively hydrogen, A is CH ₂ CH ₂ , Y is CH ₂ , t=0, others The groups are as defined in the table

Table 11: Compounds of formula (I) according to the invention, wherein Q is Q3, R ⁱ and R ^k are each methyl, R ^h and W are respectively hydrogen, t=0, and other groups are as defined in the table

Table 14: A compound of formula (I) according to the invention, which is in the form of a sodium salt, wherein Q is Q3, R ⁱ is methyl, R ^k and W are respectively hydrogen, t=0, and other groups are as shown in the table. Definition of indication

Table 17: Compounds of formula (II) according to the invention wherein Q* is chloro and R' is cyano, t is 1, and other groups are as defined in the table

B. Formulation examples

a) Dust powder is prepared by mixing 10 parts by weight of the compound of the formula (I) and/or its salts and 90 parts by weight of talc (as an inert substance), and grinding the mixture in a hammer mill.

b) The wettable powder which is easily dispersed in water is prepared by mixing 25 parts by weight of the compound of the formula (I) and/or its salt, 64 parts by weight of quartz containing kaolin (as an inert substance), and 10 parts by weight. The mixture was milled in a pinned-disk mill than potassium lignin sulfonate and 1 part by weight of sodium oleylmethyltaurate (as a wetting agent and dispersant).

c) a dispersing concentrate which is easily dispersed in water is prepared by mixing 20 parts by weight of the compound of the formula (I) and/or its salt with 6 parts by weight of an alkylphenol polyglycol ether (® Triton X 207), 3 parts by weight of isotridecyl alcohol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range is, for example, about 255 to 277 ° C or higher), and the mixture is ground in a bowl mill to Fineness below 5 microns.

d) an emulsifiable concentrate comprising 15 parts by weight of a compound of the formula (I) and/or a salt thereof, 75 parts by weight of cyclohexanone (as a solvent) and 10 parts by weight of an ethoxylated nonylphenol (made as an emulsifier).

e) The water-dispersible granule is prepared by mixing 75 parts by weight of the compound of the formula (I) and/or its salt, 10 parts by weight of calcium lignin sulfonate, and 5 parts by weight of sodium lauryl sulfate, 3 The mixture was ground in a bar disc mill with a weight ratio of polyvinyl alcohol and 7 parts by weight of kaolin. The powder was sprayed on a fluidized bed using water (as a granulating liquid) to form a granule.

f) The method for preparing the water-dispersible granules can also be homogenized and pre-ground in a colloid mill: 25 parts by weight of the compound of the formula (I) and/or its salts, 5 parts by weight of 2, 2'-two Naphthylmethane-6,6'-disulfonic acid sodium, 2 parts by weight of sodium sulphate methyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate, and 50 parts by weight The weight ratio of water was followed by grinding the mixture in a bead mill and the resulting suspension was spray dried in a spray tower using a single substance nozzle.

C. Biological examples 1. Anti-herbicide effect before the emergence of harmful plants

Seeds of monocotyledonous or dicotyledonous weeds or crops are placed in sandy loam of wood fiber pots and covered with soil. Then, according to the compound of the present invention formulated into a wettable powder (WP) or emulsion concentrate (EC) type, 0.2% of the wetting agent is added, in an aqueous suspension or emulsion form, according to 600 to 800 l/ha (after conversion) The water application rate is applied to the soil surface. After treatment, the pots were placed in a greenhouse and maintained under good growth conditions suitable for the test plants. After a three-week experimental period, the visually scored plants were tested for damage (% herbicidal activity (%): 100% active = plant dead, 0% active = like control plants) compared to the untreated control group. At this time, for example, the compounds of No. 3-160 and 4-160 showed an activity intensity of at least 80% against ramie (Abutilon theophrasti) and 苋 (Amaranthus retroflexus) at an application rate of 320 g/ha, respectively. Compound Nos. 2-160 and 10a-160 showed at least 80% activity intensity against Polygonum convolvulus and Stellaria media at an application rate of 320 g/ha, respectively.

2. Anti-herbic effect after the emergence of harmful plants

Seeds of monocotyledonous or dicotyledonous weeds or crops are placed in sandy loam of wood fiber pots, covered with soil, placed in a greenhouse, and grown under good growing conditions. After 2 to 3 weeks of sowing, the plants are treated at the first leaf stage. Then, according to the compound of the present invention formulated into a wettable powder (WP) or emulsion concentrate (EC) type, 0.2% of the wetting agent is added, in an aqueous suspension or emulsion form, according to 600 to 800 l/ha (after conversion) The water application rate is applied to the green plants. The test plants were left in the greenhouse for about 3 weeks under optimal growth conditions, and the activity of the visually-scoring preparation was compared with the untreated control group (% herbicidal activity (%): 100% activity = plant died, 0% activity = like Control plant). At this time, for example, the compounds of the numbers 2-160, 3-160, 4-160, and 10a-160 exhibit at least 80 for Abutilon theophrasti and Echinochloa crus galli at an application rate of 80 g/ha, respectively. % of activity intensity.

Claims (15)

a sulfinimide group- and sulfonimidobenzamide derivative of the formula (I), Or a salt thereof, wherein Q is a group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, R ⁶ S, R ⁷ (R ⁸ ) N, R ^b , R ^c , R ^f and R ^g are each independently hydrogen or (C ₁ -C ₄ )-alkyl, and R ^d and R ^e are respectively Independently hydrogen or (C ₁ -C ₄ )-alkyl or a carbon atom attached thereto to form a carbonyl group, ^Rh is hydrogen, (C ₁ -C ₆ )-alkylsulfonyl, (C ₁ -C ₄ )-Alkoxy-(C ₁ -C ₆ )-alkylsulfonyl, phenylsulfonyl, thiophenyl-2-sulfonyl, benzhydryl, benzhydryl-(C ₁ -C ₆ )-alkyl, benzyl, wherein the last 5 groups may need to be monosubstituted by halogen, (C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkoxy Or polysubstituted, R ⁱ is (C ₁ -C ₄ )-alkyl, R ^k is hydrogen, (C ₁ -C ₄ )-alkyl, (C ₃ -C ₇ )-cycloalkyl, A and Y are respectively Independently of oxygen, S(O) _n , N(R ³ ), carbonyl or (C ₁ -C ₄ )-alkylene, which is substituted by n R ⁹ groups and inserted into n selected from the following The elements in the group: oxygen, S(O) _n , N(R ³ ) and carbonyl, X is nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halogen - (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₎ - Alkyl, halo - (C ₃ -C ₆₎ - cycloalkyl, (C ₃ -C ₆₎ - cycloalkenyl, halo - (C ₃ -C ₆₎ - cycloalkenyl, (C ₃ -C ₆₎ -cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cyclo Alkenyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkenyl-(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 )-alkane Base, 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, benzene , heteroaryl, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ ) - an alkyl group, wherein the last six groups are respectively substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate, (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 wherein the heterocyclic group bears n pendant oxy groups, Z is hydrogen, nitro, halogen, cyano, thiocyaninyl, (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 )-cycloalkenyl, halo-(C ₃ -C ₆ )-cycloalkenyl, (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, halo-(C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ ) - alkyl, (C ₃ -C ₆₎ - cycloalkenyl, - (C ₁ -C ₆₎ - alkyl Halo - (C ₃ -C ₆₎ - cycloalkenyl, - (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, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ - C ₆₎ - alkyl, heterocyclyl - (C ₁ -C ₆₎ - alkyl, where the six last-mentioned S-th groups each consisting of each group were selected from the following group of substituents: nitro, halogen, cyano, thiocyanate acyl, (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 wherein the heterocyclic group carries n a pendant oxy group, W is hydrogen, halogen, nitro, cyano, thiocyaninyl, (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 is (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl or (C ₂ -C ₆ )-alkynyl, which are each composed of s selected from the following Group substitution in the group: nitro, halogen, cyano, thiocyaninyl, (C ₃ -C ₆ )-cycloalkyl, 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 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 S(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(R ¹ )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 C(O)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 and (R ⁵ O) ₂ (O)P, or (C ₃ -C ₆ )-cycloalkane , (C ₃ -C ₆ )-cycloalkenyl, 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 )-alkane , heterocyclic-O-(C ₁ -C ₆ )-alkyl, phenyl-N(R ¹ )-(C ₁ -C ₆ )-alkyl, heteroaryl-N(R ¹ )-( C ₁ -C ₆₎ - alkyl, heterocyclyl ^{-N (R 1) - (C} 1 -C 6) - alkyl, phenyl, _{-S (O) n - (C} 1 -C 6) - alkyl, heteroaryl group -S (O) _n - (C ₁ -C ₆ )-alkyl or heterocyclyl-S(O) _n -(C ₁ -C ₆ )-alkyl, each cyclic moiety of which is selected from the group consisting of the following: Group substitution: nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )- Cycloalkyl, 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 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 S(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(R ¹ )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 C(O)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 , and _{^{R 1 O- (C 1 -C 6}} ) - alkyl, and wherein the heterocyclyl group side with n, R 'is hydrogen, nitro, halo, cyano, (C ₁ -C ₆₎ - alkyl, halo - (C ₁ -C ₆₎ - alkyl, (C ₃ -C ₆₎ - alkenyl, halo - (C ₃ -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 ² O(O)C, (R ¹ ) ₂ N(O)C, R ² S(O)C, (R ¹ ) ₂ N(S)C, R ¹ (R ¹ O)N ( O) C, R ² (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 ) ₂ N, R ² (O) _n S, (R ² ) ₃ Si-(C ₁ -C ₆ )-alkyl-(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 ² (O) ₂ S(R ¹ )N(O) ₂ S, (R ⁵ O) ₂ (O)P, (R ² ) ₃ Si, 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 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, 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, (R ² ) ₃ Si-(C ₁ -C ₆ )-alkyl, phenyl, heteroaryl, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, Heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, wherein the last 6 phenyl, heteroaryl and heterocyclic ring Part of the group is substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate , (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 wherein the heterocyclic group carries n pendant oxy groups, R ¹ is hydrogen, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkane , (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, hetero Cyclo, 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, heterocyclic-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, wherein the last 15 groups are respectively s selected from the group consisting of the following Group substitution: nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkyl, halo-(C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-ring Alkyl, 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 wherein the heterocyclic group bears n pendant oxy groups and 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 )-cycloalkane , (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-alkyl-O-(C ₁ -C ₆ )-alkyl, ring Alkyl-(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, heterocyclic, heterocyclyl-(C ₁ -C ₆ )-alkyl, phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl group -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, a heterocyclic group -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 )- An alkyl group, a heterocyclic group-S(O) _n -(C ₁ -C ₆ )-alkyl group, wherein the last 15 groups are respectively substituted by s groups selected from the group consisting of the following groups; : nitro, halogen, cyano, thiocyanate, (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 wherein the heterocyclic group carries n pendant oxy groups, R ³ is hydrogen, (C ₁ -C ₆ )-alkane , 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 )-alkane , (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, and R ⁶ is (C ₁ -C ₄ Or a phenyl group, which is substituted by m groups selected from the group consisting of halogen, nitro, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-haloalkoxy, R ⁷ is hydrogen, (C ₁ -C ₄ )-alkyl or (C ₁ -C ₄ )-alkoxy, R ⁸ is hydrogen or (C ₁ -C ₄ )-alkyl, or R ⁷ and R ^{8 together} with the nitrogen atom to which they are attached form a 5- or 6-member saturation a partially saturated or unsaturated ring additionally comprising n heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, and substituted by m groups selected from the group consisting of halogens and cyanogens a group, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy and (C ₁ -C ₄ )-haloalkoxy, R ⁹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₄ )-halane Oxy or (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, m is 0, 1, 2, 3, 4 or 5, n is 0, 1 or 2, s is 0, 1, 2 or 3, t is 0 or 1. The sulfoximine- or sulfonimidobenzamide derivative according to Item 1 of the claim, wherein Q is a group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, and R ^b , R ^c , R ^f and R ^g are each independently hydrogen or (C ₁ -C ₄ )-alkyl, and R ^d and R ^e are each independently hydrogen or (C ₁ -C ₄ )- An alkyl group or a carbon atom to which it is attached forms a carbonyl group, ^Rh is hydrogen, R ⁱ is (C ₁ -C ₄ )-alkyl, R ^k is hydrogen, (C ₁ -C ₄ )-alkyl, C ₃ -C ₇ )-cycloalkyl, A and Y are each independently oxygen or (C ₁ -C ₄ )-alkylene, which is substituted by n R ⁹ groups, X is nitro, halogen, cyanide , (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, hetero Aryl, heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl , wherein the last six groups are substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate, (C ₁ -C ₆ )-alkane , 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 wherein the heterocyclic group bears n pendant oxy 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)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 , heterocyclic, phenyl-(C ₁ -C ₆ )-alkyl, heteroaryl-(C ₁ -C ₆ )-alkyl, heterocyclyl-(C ₁ -C ₆ )-alkyl, The six groups mentioned in the last are substituted by s groups selected from the group consisting of nitro, halogen, cyano, thiocyanate, (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 wherein the heterocyclic group carries n pendant oxy groups, W is hydrogen, halogen, nitro, cyanide a group, (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 is (C ₁ -C ₆ )-alkyl, which is substituted by s groups selected from the group consisting of halogen, cyano, (C ₃ - C ₆ )-cycloalkyl, R ¹ (O)C, R ¹ (R ¹ ON=)C, R ¹ O(O)C, (R ¹ ) ₂ N(O)C, R ² (O) ₂ S(R ¹ )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 ¹ (O)C(R ¹ )N(O) ₂ S, R ² O(O)C(R ¹ )N(O) ₂ S and (R ¹ ) ₂ N(O)C (R ¹ )N(O) ₂ S or (C ₃ -C ₆ )-cycloalkyl, which are each substituted with s groups selected from the group consisting of halogens, (C ₁ - C ₆ )-alkyl, halogen-(C ₁ -C ₆ -alkyl, (C ₃ -C ₆ )-cycloalkyl, R ¹ O(O)C and (R ¹ ) ₂ N(O)C, R' is hydrogen, nitro, cyano, (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, R ¹ (O) C, R ² O(O)C, (R ¹ ) ₂ N(O)C, R ² (O) ₂ S, 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-(C ₁ -C ₆ )- Alkyl, (R ¹ ) ₂ N-(C ₁ -C ₆ )-alkyl, R ² (O) _n S-(C ₁ -C ₆ )-alkyl, 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, heterocyclic, 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, wherein After the nine radicals mentioned are composed of s-th group was selected from each of the substituted groups: 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 wherein the heterocyclic group bears n pendant oxy 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 )-alkane , phenyl-O-(C ₁ -C ₆ )-alkyl, heteroaryl-O-(C ₁ -C ₆ )-alkyl, heterocyclyl-O-(C ₁ -C ₆ )-alkane a group in which the last 9 groups are respectively substituted by s groups selected from the group consisting of nitro, halogen, (C ₁ -C ₆ )-alkyl, halogen-(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 which N-heterocyclic group having oxo, 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 ⁹ is halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy, (C ₁ - C ₄ )-haloalkoxy or (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, n is 0, 1 or 2, and s is 0, 1, 2 or 3, t is 0 or 1. The sulfoximine- or sulfonimidobenzamide derivative according to Item 1 of the claim, wherein Q is a group Q1, Q2, Q3, Q4 or Q5, R ^a is a hydroxyl group, R ^b , R ^c , R ^f and R ^g are each independently hydrogen or a methyl group, R ^d , R ^e are hydrogen or a carbon atom attached thereto to form a carbonyl group, R ^h is hydrogen, R ⁱ Is methyl or ethyl, R ^k is hydrogen, methyl or cyclopropyl, A and Y are each independently CH ₂ or CH ₂ CH ₂ , X is nitro, halogen, methyl, ethyl, n-propyl, Isopropyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, Ethoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethoxymethyl, Methyl thiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, Z is hydrogen, nitro, cyano, halogen, methyl, ethyl, n-propyl, isopropyl, tri Fluoromethyl, difluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, pentafluoroethyl, heptafluoroisopropyl, cyclopropyl, methoxy, ethoxy, A Alkylthioalkyl, methylsulfinyl or methylsulfonyl, W is hydrogen, chlorine or methyl, R is methyl, B Or n-propyl, R 'is hydrogen or cyano group, t is 0 or 1. A herbicidal composition comprising at least one compound of the formula (I) according to claim 1 of the herbicidal activity. The herbicidal composition according to item 4 of the claim, which forms a mixture with the formulated adjuvant. A herbicidal composition according to claim 4, which comprises at least one other pesticidally active compound selected from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth agents. Conditioner. The herbicidal composition according to item 6 of the claim contains a safener. The herbicidal composition according to item 7 of the claim, which comprises cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or diphenyl Isoxadifen-ethyl. The herbicidal composition according to item 6 of the claim further comprises other herbicides. A method of controlling an undesired plant, comprising administering an effective amount of at least one compound according to formula (I) according to claim 1 or a herbicidal composition according to claim 4 to a plant or an unwanted plant Growing area. A use of a compound according to formula (I) of claim 1 or a herbicidal composition according to claim 4 for controlling undesired plants. The use of a compound of formula (I) for controlling an undesired plant in a useful crop, according to the use of claim 11. According to the use of item 12 of the claim, wherein the useful plant is a useful plant for the transfer gene. a compound of formula (II), Wherein Q* is hydroxy, ethoxy, methoxy or chloro, and R, R', X, W, Z and t are as defined in claim 1 of the claim. Use of a compound of formula (II) according to item 14 of the claim for the preparation of a compound of formula (I) according to item 1 of the claim.