Herbicidal 4-difluoromethylbenzoylamide

Abstract

To provide herbicidally active compounds alternative to existing benzoylamide herbicides.SOLUTION: Benzoylamides of the general formula (I) are described as herbicides. In this formula (I), X, R and Ra represent groups such as alkyl, cycloalkyl and halogen; and Q represents a five-membered heterocycle.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to the technical field of herbicides, in particular to herbicides for the selective control of weeds and weedy grasses in crops of useful plants. [Background technology]

[0002] WO 2011 / 035874, WO 2012 / 126932, WO 2012 / 028579 and WO 2016 / 146561 describe herbicidally active benzoylamides that differ substantially from each other depending on the nature of the heterocyclic substituent. These benzoylamides can be substituted with a number of different groups at the 2-, 3- and 4-positions of the phenyl ring. WO 2016 / 146561 discloses two compounds, 4-difluoromethyl-3-ethylsulfinyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and the sodium salt of 4-difluoromethyl-3-ethylsulfonyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide, in tabulated examples 1-38 and 1-41. However, the benzoylamides known from the above publications do not always have sufficient herbicidal efficacy and / or compatibility with crop plants. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. 2011 / 035874 Brochure [Patent Document 2] International Publication No. 2012 / 126932 Brochure [Patent Document 3] International Publication No. 2012 / 028579 Brochure [Patent Document 4] International Publication No. 2016 / 146561 Brochure Summary of the Invention [Problem to be solved by the invention]

[0004] It is an object of the present invention to provide alternative herbicidally active compounds. [Means for solving the problem]

[0005] This object is achieved by the benzoylamides according to the invention described below, which have an alkyl, cycloalkyl or halogen group in the 2-position of the phenyl ring, a sulfur-containing group in the 3-position, and a CHF2 group in the 4-position. The present invention therefore provides benzoylamides of formula (I) and salts thereof [ka] wherein the symbols and indices are defined as follows: Q is a group Q1, Q2, Q3 or Q4 [ka] represents X represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl or halogen; R represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, R a is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, halo-(C3-C6)-cycloalkyl-(C1-C6)-alkyl, R 1 (O)C-(C1-C6)-alkyl, R 1O(O)C-(C1-C6)-alkyl, (R 1 )2N(O)C—(C1–C6)-alkyl, NC—(C1–C6)-alkyl, R 1 O-(C1-C6)-alkyl, R 1 (O)CO-(C1-C6)-alkyl, R 2 (O)2SO-(C1-C6)-alkyl, (R 1 )2N-(C1-C6)-alkyl, R 1 (O)C(R 1 )N-(C1-C6)-alkyl, R 2 (O)2S(R 1 )N-(C1-C6)-alkyl, R 2 (O) n S-(C1-C6)-alkyl, R 1 O(O)2S-(C1-C6)-alkyl, (R 1 )2N(O)2S-(C1-C6)-alkyl, R 1 (O)C, R 1 O(O)C, (R 1 )2N(O)C, R 1 O, (R 1 )2N, R 2 O(O)C(R 1 )N, (R 1 )2N(O)C(R 1 )N,R 2 (O)2S, or benzyl, in each case substituted by s radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen; R X represents (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, and the above six radicals are in each case nitro, cyano, (R 6 )3Si, (R 5 O)2(O)P, R 2 (O) n S, (R 1 )2N, R 1 O, R 1 (O)C, R 1 O(O)C, R 1(O)CO, R 2 O(O)CO, R 1 (O)C(R 1 )N,R 2 (O)2S(R 1 ) substituted by s radicals from the group consisting of N, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, the last four radicals being substituted by s radicals from the group consisting of (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and halogen, and heterocyclyl bearing n oxo radicals, Or R X represents (C3-C7)-cycloalkyl, heteroaryl, heterocyclyl or phenyl, the above four radicals being in each case halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-S(O) n , (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl, R Yis hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C7)-cycloalkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy, (C2-C6)-alkenyloxy, (C2-C6)-alkynyloxy, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, acetylamino, benzoylamino, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl , ethoxycarbonylmethyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl, or heteroaryl, heterocyclyl or phenyl, the last three groups being substituted by s groups from the group consisting of (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and halogen, and heterocyclyl carrying n oxo groups, R Z is hydrogen, (C1-C6)-alkyl, R 1 O-(C1-C6)-alkyl, R'2CH2, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, R 1 O, R 1 (H)N, methoxycarbonyl, ethoxycarbonyl, methylcarbonyl, dimethylamino, trifluoromethylcarbonyl, acetylamino, methylsulfenyl, methylsulfinyl, methylsulfonyl, or heteroaryl, heterocyclyl, benzyl or phenyl, the last four groups being halogen, nitro, cyano, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C1-C6)-alkyl-S(O) n, (C1-C6)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C6)-alkoxy-(C1-C4)-alkyl, and the heterocyclyl has n oxo groups, R 1 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6 )-alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, phenyl-N(R 3 )-(C1-C6)-alkyl, heteroaryl-N(R 3 )-(C1-C6)-alkyl, heterocyclyl-N(R 3 )-(C1-C6)-Alkyl, Phenyl-S(O) n -(C1-C6)-Alkyl, Heteroaryl-S(O) n -(C1-C6)-Alkyl or Heterocyclyl-S(O) n -(C1-C6)-alkyl, the last-mentioned 15 radicals being in each case nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S, R 3 O(O)2S, (R 3 )2N(O)2S and R3 substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups; R 2 are (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkenyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)- Alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, phenyl-N(R 3 )-(C1-C6)-alkyl, heteroaryl-N(R 3 )-(C1-C6)-alkyl, heterocyclyl-N(R 3 )-(C1-C6)-Alkyl, Phenyl-S(O) n -(C1-C6)-Alkyl, Heteroaryl-S(O) n -(C1-C6)-Alkyl or Heterocyclyl-S(O) n -(C1-C6)-alkyl, the last-mentioned 15 radicals being in each case nitro, halogen, cyano, thiocyanato, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S, R 3 O(O)2S, (R 3 )2N(O)2S and R 3substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups; R 3 represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl, R 4 represents (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl or phenyl, R 5 represents hydrogen or (C1-C4)-alkyl, R 6 represents (C1-C4)-alkyl, R' represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxycarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, (C3-C6)-cycloalkyl or heteroaryl or heterocyclyl, which in each case is substituted by s radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, n represents 0, 1, or 2; s represents 0, 1, 2, or 3. (However, the compounds 4-difluoromethyl-3-ethylsulfinyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and 4-difluoromethyl-3-ethylsulfonyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and their sodium salts are excluded.)

[0006] In the groups Q1, Q2, Q3 and Q4, the arrows indicate the bond to the amide nitrogen atom of the compound of formula (I).

[0007] In formula (I) and all the following formulas, alkyl groups having 3 or more carbon atoms can be linear or branched. Examples of alkyl groups include methyl, ethyl, n-propyl or isopropyl, n-, iso-, t- or 2-butyl, pentyl, hexyl, such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, examples of alkenyl groups include allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Examples of alkynyl groups include propargyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. The multiple bond can be located at any position in each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having 3 to 6 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

[0008] Halogen is fluorine, chlorine, bromine or iodine.

[0009] Depending on the nature of the substituents and the manner in which they are attached, the compounds of general formula (I) may exist as stereoisomers. For example, when one or more asymmetrically substituted carbon atoms are present, enantiomers and diastereomers may exist. When n is 1 (sulfoxide), stereoisomers also occur. Stereoisomers can be obtained from the mixture obtained in the preparation by conventional separation methods, for example, chromatographic separation. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions with optically active starting materials and / or auxiliaries. The present invention also relates to all stereoisomers encompassed by general formula (I) but not specifically defined, and mixtures thereof.

[0010] The compounds of formula (I) can form salts. Suitable bases are, for example, organic amines (such as trialkylamines, morpholine, piperidine or pyridine), and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate and potassium bicarbonate. These salts are salts in which the acidic hydrogen is present in an agriculturally suitable cation, such as a metal salt, in particular an alkali metal or alkaline earth metal salt, in particular a sodium salt and a potassium salt, or an ammonium salt, a salt with an organic amine or a quaternary ammonium salt, for example a salt of the formula [NRRR'R''R'''] + where R to R''' each independently represent an organic group, in particular alkyl, aryl, aralkyl or alkylaryl, substituted by a cation. Also suitable are alkylsulfonium and alkylsulfoxonium salts, such as (C1-C4)-trialkylsulfonium and (C1-C4)-trialkylsulfoxonium salts.

[0011] The compounds of formula (I) can form salts through adduct formation with a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino, or pyridino, of a suitable inorganic or organic acid, such as a mineral acid, for example, HCl, HBr, HSO, HPO, or HNO, or an organic acid, for example, a carboxylic acid, for example, formic acid, acetic acid, propionic acid, oxalic acid, lactic acid, or salicylic acid, or a sulfonic acid, for example, p-toluenesulfonic acid. In such cases, the salts contain the conjugate base of the acid as the anion.

[0012] The symbols and exponents are defined as follows: Q is a group Q1, Q2, Q3 or Q4 [ka] represents X represents (C1-C6)-alkyl or (C3-C6)-cycloalkyl, R represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, R a represents hydrogen, R X represents (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, and the above six groups are in each case R 2 (O) n S, (R 1 )2N, R 1 O, R 1 (O)C, R 1 O(O)C, R 1 (O)CO, R 2 O(O)CO, R 1 (O)C(R 1 )N,R 2 (O)2S(R 1 ) substituted by s radicals from the group consisting of N, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, the last four radicals being substituted by s radicals from the group consisting of (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halogen, and heterocyclyl bearing n oxo radicals, Or R X represents (C3-C7)-cycloalkyl, which is substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl and halo-(C1-C6)-alkyl, R Y represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, (C1-C6)-alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino, aminocarbonyl or methoxymethyl, R Z is hydrogen, (C1-C6)-alkyl, R 1O-(C1-C6)-alkyl, R'CH2, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, R 1 O, R 1 (H) represents N, methoxycarbonyl, acetylamino or methylsulfonyl; R 1 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl , heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, the last-mentioned nine radicals being in each case nitro, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S and R 3 substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups, R 2are (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, he Heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, the last-mentioned nine radicals being in each case nitro, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S and R 3 substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups, R 3 represents hydrogen or (C1-C6)-alkyl, R 4 represents (C1-C6)-alkyl; R' represents acetoxy, acetamido, methoxycarbonyl or (C3-C6)-cycloalkyl; n represents 0, 1, or 2; s represents 0, 1, 2 or 3; Compounds of general formula (I) are preferred.

[0013] The symbols and exponents are defined as follows: Q is a group Q1, Q2, Q3 or Q4 [ka] represents X represents a halogen; R represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, R a represents hydrogen, R X represents (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C2-C6)-alkenyl, halo-(C2-C6)-alkenyl, (C2-C6)-alkynyl, halo-(C3-C6)-alkynyl, and the above six groups are in each case R 2 (O) n S, (R 1 )2N, R 1 O, R 1 (O)C, R 1 O(O)C, R 1 (O)CO, R 2 O(O)CO, R 1 (O)C(R 1 )N,R 2 (O)2S(R 1 ) substituted by s radicals from the group consisting of N, (C3-C6)-cycloalkyl, heteroaryl, heterocyclyl and phenyl, the last four radicals being substituted by s radicals from the group consisting of (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C1-C6)-alkoxy and halogen, and heterocyclyl bearing n oxo radicals, Or R X represents (C3-C7)-cycloalkyl, which is substituted by s radicals from the group consisting of halogen, (C1-C6)-alkyl and halo-(C1-C6)-alkyl, R Y represents hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C7)-cycloalkyl, (C1-C6)-alkoxy, methoxycarbonyl, methoxycarbonylmethyl, halogen, amino, aminocarbonyl or methoxymethyl, R Z is hydrogen, (C1-C6)-alkyl, R 1O-(C1-C6)-alkyl, R'CH2, (C3-C7)-cycloalkyl, halo-(C1-C6)-alkyl, R 1 O, R 1 (H) represents N, methoxycarbonyl, acetylamino or methylsulfonyl; R 1 is hydrogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl , heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, the last-mentioned nine radicals being in each case nitro, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S and R 3 substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups, R 2are (C1-C6)-alkyl, halo-(C1-C6)-alkyl, (C3-C6)-cycloalkyl, halo-(C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, cycloalkyl-(C1-C6)-alkyl-O-(C1-C6)-alkyl, phenyl, phenyl-(C1-C6)-alkyl, he Heteroaryl, heteroaryl-(C1-C6)-alkyl, heterocyclyl, heterocyclyl-(C1-C6)-alkyl, phenyl-O-(C1-C6)-alkyl, heteroaryl-O-(C1-C6)-alkyl, heterocyclyl-O-(C1-C6)-alkyl, the last-mentioned nine radicals being in each case nitro, halogen, (C1-C6)-alkyl, halo-(C1-C6)-alkyl, R 3 O(O)C, (R 3 )2N(O)C, R 3 O, (R 3 )2N, R 4 (O) n S and R 3 substituted by s groups from the group consisting of O-(C1-C6)-alkyl, and heterocyclyl has n oxo groups, R 3 represents hydrogen or (C1-C6)-alkyl, R 4 represents (C1-C6)-alkyl; R' represents acetoxy, acetamido, methoxycarbonyl or (C3-C6)-cycloalkyl; n represents 0, 1, or 2; s represents 0, 1, 2 or 3; Compounds of general formula (I) are also preferred.

[0014] The symbols and exponents are defined as follows: Q is a group Q1, Q2, Q3 or Q4 [ka] represents X represents methyl, ethyl or cyclopropyl; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; R a represents hydrogen, R X represents methyl, ethyl or n-propyl; R Y represents methyl or chlorine, R Z represents methyl, n represents 0, 1 or 2; Compounds of general formula (I) are very particularly preferred.

[0015] The symbols and exponents are defined as follows: Q is a group Q1, Q2, Q3 or Q4 [ka] represents X represents fluorine, chlorine, bromine or iodine; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; R a represents hydrogen, R X represents methyl, ethyl or n-propyl; R Y represents methyl or chlorine, R Z represents methyl, n represents 0, 1 or 2; Compounds of the general formula (I) are also very particularly preferred.

[0016] In all formulas specified below, the substituents and symbols have the same meaning as described in formula (I) unless defined differently.

[0017] The compounds of the invention in which Q represents Q1 or Q2, as well as the aminotetrazoles and aminotriazoles on which their amides are based, can be prepared, for example, by the methods specified in WO 2012 / 028579.

[0018] The compounds of the invention in which Q represents Q3, and the aminofurazans on which these amides are based, can be prepared, for example, by the methods specified in WO 2011 / 035874.

[0019] Compounds of the invention in which Q is Q4 can be prepared, for example, by the methods specified in WO 2012 / 126932. The 2-amino-1,3,4-oxadiazoles on which these amides are based are commercially available or can be obtained synthetically by standard methods known from the literature.

[0020] The benzoyl chlorides, or the corresponding benzoic acids, which are the basis of the compounds (I) according to the invention can be prepared, for example, by the method shown in Scheme 1. The 2-hydroxybenzoic acid esters required for this purpose can be obtained by the method specified in WO 2014 / 090766 (see in particular Synthesis Example 2 on page 6 of that document): methylation of the hydroxyl group, followed by ester hydrolysis. After formation of the oxazoline group, the methoxy group can be nucleophilically exchanged with an alkyl, cycloalkyl, or amino group (A.I. Meyers et al., J. Org. Chem., 1978, 43(7), 1372-1379; A.I. Meyers et al., J. Org. Chem., 1977, 42(15), 2653-2654; A.I. Meyers et al., Tetrahedron, 1994, 50(8), 2297-2360; T.W. Greene and P.G. M. Butts, Protective Groups in Organic Synthesis, 2nd ed., John Wiley & Sons, Inc. 1991, pp. 265ff.; Z. Hell et al., Tetrahedron Letters, 2002, 43, 3985-3987.). Subsequent oxazoline cleavage affords substituted 4-difluoromethylbenzoic acids, which can be further modified depending on the desired substitution pattern. For example, 2-aminobenzoic acids can be converted to 2-halobenzoic acids via a Sandmeyer reaction.

[0021] Scheme 1 [ka] The prior art, for example Y. Lu, C. Liu, Q.-Y. Chen, Curr. Org. Chem., 2015, 19, 1638-1650, discloses several other methods for introducing difluoromethyl groups.

[0022] The thioethers can be further oxidized to the corresponding sulfoxides or sulfones, for example according to Scheme 2. Oxidation methods that selectively lead to sulfoxides or sulfones are known from the literature. Some oxidation systems are suitable, for example peracids such as metachloroperbenzoic acid, which may be generated in situ (e.g., peracetic acid in the acetic acid / hydrogen peroxide / sodium tungstate(VI) system) (Houben-Weyl, Methoden der Organischen Chemie [Methods of Organic Chemistry], Georg Thieme Verlag Stuttgart, Vol. E11, Expanded and Supplementary Volume 4 of the 1985 Edition, pp. 702 ff., 718 ff. and 1194 ff.).

[0023] The substitution pattern and oxidizing agent are among the factors that determine the point in the synthetic cascade at which oxidation of the thioether is appropriate. For example, as shown in Scheme 2, oxidation of the thioether can be performed at the free benzoic acid stage or at the stage of the thioether represented by formula (I) (wherein R a Oxidation at the amide stage (n = H and n = 0) may be appropriate.

[0024] Scheme 2 [ka] It may be appropriate to change the order of the reaction steps. For example, a benzoic acid bearing a sulfoxide cannot be directly converted to its acid chloride. One option here is to first convert the benzoic acid bearing a sulfoxide to the corresponding acid chloride of formula (I) (where R a =H and n=0) and then oxidizing the thioether to the sulfoxide.

[0025] The work-up of the respective reaction mixture is generally carried out by known methods, such as crystallization, aqueous extractive work-up, chromatographic methods or a combination of these methods.

[0026] The preparation of compounds (I) according to the invention can proceed via the substituted benzoic acids of formula (II) or the corresponding benzoyl chlorides of formula (III), as described above.

[0027] The compounds of formula (II) are novel and are highly suitable as intermediates for preparing the compounds of formula (I) according to the invention. Therefore, the present invention further provides compounds of formula (II) [ka] (wherein the symbols and indices are defined as follows: X represents (C3-C6)-cycloalkyl or halogen; R represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, (C1-C6)-alkyl-O-(C1-C6)-alkyl, (n represents 0, 1 or 2) to provide.

[0028] X represents cyclopropyl, fluorine, chlorine, bromine or iodine; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; n represents 0, 1 or 2; Compounds of formula (II) are preferred.

[0029] The compounds of formula (III) are likewise novel and are highly suitable as intermediates for preparing the compounds of formula (I) according to the invention. The present invention therefore further provides compounds of formula (III) [ka] (wherein the symbols and indices are defined as follows: X represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl or halogen; R represents (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-cycloalkyl-(C1-C6)-alkyl, or (C1-C6)-alkyl-O-(C1-C6)-alkyl. (n represents 0, 1 or 2) to provide.

[0030] X represents methyl, ethyl, cyclopropyl, fluorine, chlorine, bromine or iodine; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; n represents 0, 1 or 2; Compounds of formula (III) are preferred.

[0031] The set of compounds of formula (I) and / or their salts that can be synthesized by the above-mentioned reactions can also be prepared in a parallelized manner, and in this case, this can be achieved manually, partially automated, or fully automated. For example, it is possible to automate the reaction, workup, or purification of products and / or intermediates. In general, this is understood to mean, for example, the procedure described in D. Tiebes, Combinatorial Chemistry - Synthesis, Analysis, Screening (editor Gunther Jung), Wiley, 1999, pp. 1-34.

[0032] For parallelized reaction and workup, several commercially available equipment can be used, such as Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA, or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, UK, or MultiPROBE Automated Workstations from Perkin Elmer, Waltham, Massachusetts 02451, USA. For parallelized purification of compounds of general formula (I) and their salts or intermediates occurring in the course of their preparation, available equipment includes, for example, chromatography equipment from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.

[0033] The described apparatus results in a modular procedure in which individual work steps are automated, but manual intervention is required between work steps. This can be avoided by using a partially or fully integrated automation system in which each automation module is operated, for example, by a robot. Automation systems of this type can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.

[0034] The implementation of single or multiple synthetic steps can be based on the use of polymer-supported reagents / scavenging resins. Specialist literature, such as ChemFiles, Vol. 4, No. 1, Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich), provides a range of experimental protocols.

[0035] In addition to the methods described herein, the compounds of general formula (I) and their salts can be prepared completely or partially by solid-phase support methods. For this purpose, individual or all intermediates in the synthesis or the corresponding procedure-compatible synthesis are bound to a synthetic resin. Solid-phase support synthesis methods are fully described in technical literature, for example, Barry A. Bunin, "The Combinatorial Index," Academic Press, 1998, and Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Gunther Jung), Wiley, 1999. The use of solid-phase support synthesis methods allows for several protocols known from the literature, some of which can be carried out manually or in an automated manner. The reaction can be carried out, for example, by IRORI technology in a microreactor at Nexus Biosystems, 12140 Community Road, Poway, CA 92064, USA.

[0036] The implementation of individual or several synthesis steps, both in solid and liquid phase, can be based on the use of microwave technology. Specialist literature, such as Microwaves in Organic and Medicinal Chemistry (editors: C. O. Kappe and A. Stadler), Wiley, 2005, describes a range of experimental protocols.

[0037] Preparation by the methods described herein results in compounds of formula (I) and salts thereof in the form of a collection of substances called a library. The present invention also provides libraries comprising at least two compounds of formula (I) and salts thereof.

[0038] The compounds of the present invention have excellent herbicidal activity against a wide range of economically important mono- and dicotyledonous annual harmful plants. The active compounds also act efficiently on difficult-to-control perennial weeds that produce shoots from rhizomes, rootstocks, and other perennial organs.

[0039] Thus, the present invention also provides a method for controlling unwanted plants or, preferably, regulating plant growth in plant crops, by applying one or more compounds of the present invention to plants (e.g., monocotyledonous or dicotyledonous weeds or unwanted crop plants), seeds (e.g., grains, seeds, or vegetative propagules, such as tubers or shoot portions bearing buds), or the area where the plants grow (e.g., the area under cultivation). The compounds of the present invention can be applied, for example, before sowing (by incorporation into the soil, if appropriate), before emergence, or after emergence. Although it is not intended to limit the list to specific species, some representative examples of monocotyledonous and dicotyledonous weed flora that can be controlled by the compounds of the present invention are as follows:

[0040] Genera of monocotyledonous harmful plants: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrost is), Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria and Sorghum.

[0041] Dicotyledonous weed genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Thistle (Cirsium), Bindweed (Convolvulus), Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lamium Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, and Cyperus. Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica,Viola and Xanthium.

[0042] When the compounds of the present invention are applied to the soil surface pre-emergence, they either completely prevent weed seedling emergence or allow weeds to grow until they reach the cotyledon stage, after which they cease growth and ultimately die completely after 3-4 weeks.

[0043] If the active compounds are applied to the green parts of the plants after emergence, growth stops after treatment and the harmful plants remain in the vegetative stage at the time of application or they die completely after a certain period of time, thus resulting in a very rapid and lasting elimination of competition by harmful weeds for the crop plants.

[0044] The compounds of the present invention have significant herbicidal activity against monocotyledonous and dicotyledonous weeds, but are not effective against economically important crops such as Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Na, The structure and application rate of the specific compounds of the present invention only slightly damages monocotyledonous crop plants of the genera Solanum, Vicia, or Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, especially monocotyledonous crop plants of Zea and Triticum. For these reasons, the compounds are highly suitable for selectively controlling unwanted plant growth in plant crops, such as agriculturally useful or ornamental plants.

[0045] Furthermore, depending on the specific chemical structure and application rate used, the compounds of the present invention have significant growth-regulating properties in crop plants.These compounds can intervene in the metabolism of plants themselves through regulating effects, and can be used to control the effects of plant components and, for example, to facilitate harvesting by causing drought and stunting.In addition, they are also suitable for general control and inhibition of unwanted vegetative growth without killing plants.Inhibition of vegetative growth plays an important role for many mono- and dicotyledonous crops, for example, because it can reduce or completely prevent lodging.

[0046] Due to its herbicidal and plant growth regulating properties, active compounds can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis.Generally, transgenic plants are characterized by specific advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or plant disease pathogens (such as certain insects or microorganisms (such as fungi, bacteria, or viruses)).Other specific properties are related to the harvested material, for example, in terms of quality, quantity, storability, composition, and specific components.For example, transgenic plants with increased starch content or altered starch quality, or those with different fatty acid compositions in the harvested material are known.

[0047] The use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, for example cereals such as wheat, barley, rye, oats, millet / sorghum, rice and maize or crops of sugar beet, cotton, soybean, oilseed rape, potato, manioc, tomato, pea and other vegetables, is preferred in relation to transgenic crops.

[0048] Preferably, the compounds of the invention can be used as herbicides in crops of useful plants that are tolerant or have been made tolerant by genetic engineering to the phytotoxic effects of herbicides.

[0049] Conventional methods for creating new plants with modified characteristics compared to existing plants include, for example, traditional cultivation methods and the generation of mutants. Alternatively, new plants with modified characteristics can be created using recombinant methods (see, for example, EP 0221044, EP 0131624). For example, in some cases, the following is described: Genetic modification of crop plants with the aim of modifying the starch synthesized in the plants (e.g. WO 92 / 11376, WO 92 / 14827, WO 91 / 19806), transgenic crop plants that are resistant to certain herbicides of the glufosinate type (see, for example, EP 0242236, EP 242246) or glyphosate type (WO 92 / 00377) or sulfonylurea type (EP 0257993, U.S. Pat. No. 5,013,659); transgenic crop plants, such as cotton, capable of producing Bacillus thuringiensis toxins (Bt toxins) that render the plants resistant to certain pests (EP 0142924, EP 0193259); Transgenic crop plants with modified fatty acid composition (WO 91 / 13972); Genetically modified crop plants with novel components or secondary metabolites, such as novel phytoalexins, that result in increased disease resistance (EP 309862, EP 0464461); Genetically modified plants with reduced photorespiration, with higher yields and greater stress tolerance (EP 0305398); transgenic crop plants producing proteins of pharmaceutical or diagnostic importance ("molecular farming"); Transgenic crop plants characterized by higher yield or better quality, For example, transgenic crop plants characterized by combinations of the above novel traits ("gene stacking").

[0050] Numerous molecular biological techniques are known in principle that can be used to generate novel transgenic plants with modified properties; see, for example, I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, Trends in Plant Science 1 (1996) 423-431.

[0051] For such genetic manipulation, nucleic acid molecules that allow for recombination mutagenesis or sequence changes of DNA sequences can be introduced into a plasmid. Standard methods can be used, for example, to perform base exchange, remove part of the sequence, or add natural or synthetic sequences. To link DNA fragments to each other, adapters or linkers can be placed on the fragments. For example, see 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" [Genes and clones], VCH Weinheim, 2nd Edition 1996.

[0052] For example, the creation of plant cells with reduced gene product activity can be achieved by expressing at least one corresponding antisense RNA, sense RNA, or at least one appropriately constructed ribozyme that specifically cleaves the transcript of the gene product to achieve a cosuppression effect. To achieve this goal, DNA molecules containing the entire coding sequence of the gene product, including any adjacent sequences that may be present, and DNA molecules containing only portions of the coding sequence (in this case, these portions must be long enough to have an antisense effect in cells) can also be used. DNA sequences that are highly homologous to the coding sequence of the gene product but not completely identical to it can also be used.

[0053] When expressing nucleic acids in plants, the synthesized protein can be localized in any desired compartment of the plant cell. However, to achieve localization in a specific compartment, for example, a coding region ensuring localization to a specific compartment can be linked to the DNA sequence. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; 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.

[0054] Transgenic plant cells can be produced by known techniques to give rise to whole plants. In principle, the transgenic plants can be of any desired plant species, i.e., dicotyledonous as well as monocotyledonous plants.

[0055] Thus, transgenic plants can be obtained whose properties are altered by the overexpression, suppression or inhibition of a homologous (= natural) gene or gene sequence or by the expression of a heterologous (= foreign) gene or gene sequence.

[0056] The compounds of the invention can preferably be used in transgenic crops that are tolerant to growth regulators, such as dicamba, or to herbicides that inhibit essential plant enzymes, such as acetolactate synthase (ALS), EPSP synthase, glutamine synthase (GS) or hydroxyphenylpyruvate dioxygenase (HPPD), or to herbicides from the group of sulfonylureas, glyphosate, glufosinate or benzoylisoxazoles and similar active substances.

[0057] When the active compounds of the invention are used in transgenic crops, not only do they produce the effects against harmful plants observed in other crops, but they also often produce effects specific to application to a particular transgenic crop, such as a changed or specifically expanded spectrum of weeds that can be controlled, changes in the application rates that can be used for application, preferably better combinations with herbicides to which the transgenic crop is tolerant, and effects on the growth and yield of the transgenic crop plants.

[0058] Therefore, the present invention also provides the use of the compounds of the invention as herbicides for controlling harmful plants in transgenic crop plants.

[0059] The compounds of the present invention can be applied in the form of wettable powders, emulsifiable concentrates, sprays, dustable products or granules in conventional formulations. Thus, the present invention also provides herbicidal and plant growth regulating compositions comprising the compounds of the present invention.

[0060] The compounds of the present invention can be formulated in various ways according to the required biological and / or physicochemical parameters. Possible formulations include, for example, wettable powders (WP), water-soluble powders (SP), water-soluble solutions, emulsifiable concentrates (EC), emulsion concentrates (EW), such as oil-in-water and water-in-oil emulsions, sprays, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dustable products (DP), dressings, granules for scattering and solid application, microgranules, spray granules, granules (GR) in the form of absorbents and adsorbents, 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, by Winnacker-Kuchler, "Chemische Technologie" [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.

[0061] The necessary formulation auxiliaries (such as inert materials, surfactants, solvents and further additives) are also known and are found, 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, "Solvents Guide", 2nd Edition, Interscience, NY 1963; McCutcheon, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schonfeldt, "Grenzflachenaktive Athylenoxidaddukte" [Interface-active Ethylene Oxide Adducts], Wiss.Verlagsgesellschaft, Stuttgart 1976; Winnacker-Kuchler, "Chemische Technologie" [Chemical Engineering], Vol. 7, C. Hanser Verlag Munich, 4th edition 1986.

[0062] Wettable powders are preparations that can be uniformly dispersed in water and contain, in addition to the active compound, diluents or inert substances, ionic and / or nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate, or sodium oleoylmethyl taurate. To prepare wettable powders, the herbicidally active compound is finely ground using conventional equipment, such as a hammer mill, blower mill, or air-jet mill, and simultaneously or subsequently mixed with formulation adjuvants.

[0063] Emulsifiable concentrate is prepared by dissolving active compound in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or a mixture of relatively high-boiling aromatic or hydrocarbon or organic solvent, with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).The emulsifiers that can be used include calcium alkylarylsulfonate (such as calcium dodecylbenzenesulfonate) or nonionic emulsifiers (fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensates, alkyl polyethers, sorbitan esters, such as sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, such as polyoxyethylene sorbitan fatty acid esters).

[0064] Dustable products are obtained by grinding the active compound with finely dispersed solids, for example talc, natural clays (such as kaolin, bentonite and pyrophyllite) or diatomaceous earth.

[0065] Suspensions may be water-based or oil-based and can be prepared, for example, by wet milling using commercially available bead mills, with the optional addition of surfactants, for example, as already listed above for the other formulation types.

[0066] Emulsion formulations, for example oil-in-water emulsion formulations (EW), can be prepared using aqueous organic solvents and, optionally, surfactants, for example, as already listed above for other formulation types, using a stirrer, colloid mill and / or static mixer.

[0067] Granules can be prepared by spraying the active compound onto an adsorbent granular inert material or by applying an active compound concentrate to the surface of a carrier (such as sand, kaolinite, or a granular inert material) using an adhesive such as polyvinyl alcohol, sodium polyacrylate, or mineral oil. If a mixture with a fertilizer is desired, the appropriate active compound can also be granulated in a manner conventional for producing fertilizer granules.

[0068] Water dispersible granules are generally prepared by conventional methods such as spray drying, fluidized bed granulation, pan granulation, high speed mixer mixing, and extrusion without solid inert materials.

[0069] For the preparation of pan, flow, extrusion and spray granules, see, for example, the methods in "Spray-Drying Handbook", 3rd Edition 1979, G. Goodwin Ltd., London, J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pp. 147ff; "Perry's Chemical Engineer's Handbook", 5th Edition, McGraw Hill, New York 1973, pp. 8-57.

[0070] For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0071] The pesticide formulation generally contains 0.1% to 99% by weight, particularly 0.1% to 95% by weight, of the compound of the present invention.

[0072] In wettable powders, the active compound concentration is, for example, about 10% to 90% by weight, with the remainder consisting of conventional formulation ingredients up to 100% by weight. In emulsifiable concentrates, the active compound concentration can be about 1% to 90% by weight, preferably 5% to 80% by weight. Powder formulations are They contain 1% to 30% by weight of active compound, preferably usually 5% to 20% by weight; spray solutions contain about 0.05% to 80% by weight, preferably 2% to 50% by weight, of the active compound. In the case of water dispersible granules, the active compound content depends in part on whether the active compound is in liquid or solid form and which granulation aids, fillers, etc. are used. In water dispersible granules, the active compound content is, for example, between 1% and 95% by weight, preferably between 10% and 80% by weight.

[0073] Furthermore, the active compound formulations mentioned may optionally contain the respective customary spreading agents, wetters, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, antifoaming agents, evaporation inhibitors and agents for influencing pH and viscosity.

[0074] Based on these formulations, it is also possible to prepare combinations with other pesticide active substances, such as insecticides, acaricides, herbicides, fungicides, as well as safeners, fertilizers and / or growth regulators, for example in the form of finished formulations or as tank mixes.

[0075] For application, the commercially available formulations are diluted, if appropriate, in the customary manner, for example with water in the case of wettable powders, emulsifiable concentrates, dispersions and water dispersible granules. Dust formulations, granules for soil application or scattering granules and spray solutions are usually not further diluted with other inert substances before application.

[0076] The required application rate of the compounds of formula (I) varies depending on the external conditions, including inter alia temperature, humidity and the type of herbicide used, and may vary within a wide range, for example from 0.001 to 1.0 kg / ha or more of active substance, but is preferably from 0.005 to 750 g / ha. DETAILED DESCRIPTION OF THE INVENTION

[0077] The following examples illustrate the invention.

[0078] Chemical Examples Synthesis of 4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide (Example No. 4-1) Step 1: Synthesis of ethyl 4-difluoromethyl-2-methoxy-3-methylthiobenzoate 66.02 g (477.7 mmol) of potassium carbonate was added to 104.4 g (398.1 mmol) of ethyl 4-difluoromethyl-2-hydroxy-3-methylthiobenzoate in 310 ml of acetone. A mixture of 6.04 g (59.7 mmol) of triethylamine and 7.53 g (59.7 mmol) of dimethyl sulfate was then added. 57.74 g (457.8 mmol) of dimethyl sulfate was then added dropwise. The reaction mixture was then stirred at room temperature (RT) for 16 hours. For workup, the solvent was removed from the reaction mixture, and the residue was stirred with 1000 ml of 1 M aqueous sodium hydroxide solution for 2 hours. CHCl was added to the mixture, and after phase separation, the organic phase was dried. The solvent was removed from the filtrate. 104.7 g of the desired product was obtained as a residue.

[0079] Step 2: Synthesis of 4-difluoromethyl-2-methoxy-3-methylthiobenzoic acid 104.7 g (378.9 mmol) of ethyl 4-difluoromethyl-2-methoxy-3-methylthiobenzoate was stirred with a mixture of 420 ml of 1 M aqueous sodium hydroxide solution and 715 ml of methanol at room temperature for 16 hours. For workup, the methanol was removed. The residue was extracted with ethyl acetate, and the aqueous phase was then acidified with hydrochloric acid. The mixture was then extracted twice with ethyl acetate. The combined organic phases were dried, and the solvent was removed from the filtrate. 90.0 g of the desired product was obtained as a residue.

[0080] Step 3: Synthesis of 2-[4-(difluoromethyl)-2-methoxy-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole 1.24 ml (16.1 mmol) of N,N-dimethylformamide was added to 40.0 g (161.1 mmol) of 4-difluoromethyl-2-methoxy-3-methylthiobenzoate in 600 ml of dichloromethane. 23.2 ml (265.9 mmol) of oxalyl chloride was then added dropwise. The reaction mixture was stirred at room temperature for 16 hours. 2.81 ml (32.2 mmol) of oxalyl chloride was then added to complete the reaction, and the mixture was stirred at room temperature for an additional 24 hours. The contents were then concentrated, and the residue was dissolved in CHCl. The residue was redissolved in 00 ml of 10% sodium hydroxide solution. Then, a solution of 15.08 g (169.2 mmol) of 2-amino-2-methyl-1-propanol in 10% sodium hydroxide solution was added dropwise with slight ice-bath cooling. The mixture was stirred at room temperature for 24 hours. For workup, the mixture was first diluted with CHCl and then with a small amount of water. After phase separation, the aqueous phase was extracted with CHCl. ​​The combined organic phases were extracted, and the filtrate was concentrated. In the second reaction step, the residue was dissolved in 600 ml of CHCl, and 32.9 ml (451.2 mmol) of thionyl chloride was added. The reaction mixture was then stirred at room temperature for 16 hours. For workup, 500 ml of 10% sodium hydroxide solution was added over 2 hours with ice-bath cooling, followed by another 100 ml of 10% sodium hydroxide solution. After phase separation, the aqueous phase was extracted with CHCl. ​​The combined organic phases were dried, and the filtrate was concentrated. 200 ml of 6 M hydrochloric acid was added to the residue, and the mixture was extracted three times with 60 ml of CHCl. ​​The combined organic phase was extracted twice with 25 ml of 6 M hydrochloric acid, then twice with 20 ml of 6 M hydrochloric acid. The hydrochloric acid phase was cooled in an ice bath and made alkaline by adding solid NaOH a little at a time. The mixture was then extracted twice with 200 ml of CHCl, then once more with 100 ml of CHCl. ​​The organic phase was dried, and the solvent was removed from the filtrate. 32.6 g of the desired product was obtained as a residue.

[0081] Step 4: Synthesis of 2-[4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole At room temperature, 84.6 ml (84.6 mmol) of a 1 M solution of methylmagnesium bromide in THF was added dropwise to a solution of 17.0 g (56.4 mmol) of 2-[4-(difluoromethyl)-2-methoxy-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole in 280 ml of diethyl ether. After 2 hours, 56 ml (56 mmol) of a 1 M solution of methylmagnesium bromide in THF was added dropwise over 3 hours. The mixture was stirred at room temperature for 72 hours. For workup, the contents were carefully poured into a mixture of ice and dilute hydrochloric acid. The mixture was neutralized with NaOH and extracted twice with diethyl ether. The organic phase was dried, and the solvent was removed from the filtrate. 15.9 g of the desired product was obtained as a residue.

[0082] Step 5: Synthesis of 4-difluoromethyl-2-methyl-3-methylthiobenzoic acid 30.9 ml (497 mmol) of iodomethane was added to 15.47 g (54.2 mmol) of 2-[4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)phenyl]-4,4-dimethyl-4,5-dihydro-1,3-oxazole in 250 ml of acetone, and the mixture was stirred at 40°C for 2 hours. Another 25 ml (402 mmol) of iodomethane was then added, and the mixture was then stirred at 40°C for 20 hours. To complete the reaction, another 10 ml (161 mmol) of iodomethane was then added, and the mixture was then stirred at 40°C for 15 hours. For workup, the reaction mixture was cooled to room temperature and concentrated. For the second reaction step, 150 ml of methanol and 150 ml of 20% strength aqueous sodium hydroxide solution were added to the residue, and the mixture was heated under reflux for 2 hours. Finally, the reaction mixture was stirred at room temperature for 72 hours. For workup, the contents were concentrated and the residue was dissolved in a small amount of water. The mixture was washed with CH2Cl2, and the aqueous phase was acidified with concentrated hydrochloric acid. The mixture was then extracted with CH2Cl2. The solvent was removed from the organic phase. 11.8 g of the desired product was obtained as a residue.

[0083] Step 6: Synthesis of 4-(difluoromethyl)-2-methyl-3-(methylsulfanyl)-N-(1-methyl-1H-1,2,4-triazol-5-yl)benzamide (No. 4-1) At room temperature, 137.4 mg (1.4 mmol) of 1-methyl-1H-1,2,4-triazol-5-amine was added to 232.2 mg (1.0 mmol) of 4-difluoromethyl-2-methyl-3-methylthiobenzoic acid in 5 ml of pyridine. With cooling, 177.7 mg (1.4 mmol) of oxalyl chloride was added, and the mixture was then stirred at room temperature for 16 hours. For workup, the mixture was concentrated and the residue was dissolved in CHCl. ​​The mixture was extracted once with aqueous NaHCO and then once with water. The organic phase was dried, and the filtrate was concentrated. The residue was purified by chromatography, and 62.6 mg of the desired product was isolated.

[0084] The examples listed in the table below were prepared or can be obtained analogously to the methods described above: These compounds are very particularly preferred.

[0085] The abbreviations used stand for the following: Ph = Phenyl, Me = Methyl, Et = Ethyl, c-Pr = Cyclopropyl

[0086] [Table 1A] [Table 1B] [Table 1C]

[0087] [Table 2A] [Table 2B] [Table 2C]

[0088] Table 3A Table 3B Table 3C

[0089] Table 4A Table 4B Table 4C

[0090] Table 5A Table 5B Table 5C

[0091] Table 6A Table 6B Table 6C

[0092] Table 7A Table 7B [Table 7C]

[0093] [Table 8A] [Table 8B] [Table 8C]

[0094] [Table 9A] [Table 9B]

[0095] [Table 10A] [Table 10B] [Table 10C]

[0096] NMR data for a number of compounds of formula (I) according to the invention referred to in the above table are disclosed below using the NMR peak listing method. 1 H NMR data 1 The peaks are listed in the form of a H NMR peak list. For each signal peak, the δ value (ppm) is listed first, followed by the signal intensity in parentheses. The δ value-signal intensity number pairs for different signal peaks are listed, separated from each other by semicolons. Thus, the peak list for one example takes the following form: δ1 (Intensity 1); δ2 (Intensity 2);........;δ i (strengthi );........;δ n (strength n ).

[0097] The intensity of sharp signals correlates with the signal height (cm) in the printed example of the NMR spectrum, giving the correct ratio of signal intensities. In the case of broad signals, several peaks or signal centers can be shown and their intensities compared to the most intense signal in the spectrum. 1 The H NMR peak list is conventional 1 It is similar to a H NMR printout and therefore usually includes all peaks listed in the conventional NMR interpretation. 1 Like 1 H NMR printouts, these may show solvent signals as well as signals of stereoisomers of target compounds provided by the present invention, and / or peaks of impurities.

[0098] When reporting compound signals in the δ range of the solvent and / or water, 1 The 1 H NMR peak list shows standard solvent peaks, e.g., the DMSO peak in DMSO-D6, and the water peak, which usually have high average intensities.

[0099] The peaks of stereoisomers and / or impurity peaks of the compounds of the invention typically have lower intensities on average than the compounds of the invention (eg, having a purity of greater than 90%).

[0100] Such stereoisomers and / or impurities may be unique to a particular preparation method, and thus the peaks may be useful in identifying the reproduction of the preparation method by reference to a "by-product fingerprint."

[0101] The expert, who calculates the peaks of the target compounds by known methods (MestreC, ACD simulations, but also using empirically evaluated expectation values), can optionally use additional intensity filters to isolate the peaks of the compounds of the invention, if necessary. 1This would be similar to problematic peak picking in H NMR interpretation. Example 1-1: 1 H-NMR(400.0 MHz, CDCl3):δ=7.79(0.78);7.77(1.41);7.723(1.33);7.703(0.72);7.518(0.54);7.506(1.01);7.368(2.17);7.26(92.56);7.22 9(1.07);6.996(0.51);4.127(14.78);2.797(9.61);2.308(16);2.252(0.56);1.553(1.29);0.008(1.14);0(32.43);-0.008(0.97) Example 1-2: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.755(0.94);7.995(0.74);7.923(0.57);7.902(0.93);7.842(1.16);7.821(0. 68);4.007(16);3.311(53.71);3.002(12.55);2.674(0.69);2.669(0.92);2.665(0.7);2.59(7.06 );2.523(2.83);2.518(4.26);2.51(55.71);2.505(120.68);2.5(167.23);2.496(116.4);2.491(51.7);2.45(0.53);2.332(0.71);2.327(0.96);2.323(0.69);0.008(0.95);0(31.89);-0.008(0.89) Example 1-3: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.829(0.84);8.047(0.55);7.937(0.88);7.919(0.94);7.783(1.21);7.646(0.6);4.021(16);3.446(10.93);3.309(31.28);2.75(7.59);2.669(0.55);2.523(1.58);2.518(2.4);2.509(30.08);2.505(65.21);2.5(91.14);2.496(63.77);2.491(28.46);2.327(0.53);0.008(0.54);0(17.36) Example 1-4: 1 H-NMR(400.0 MHz,CDCl3):δ=7.778(0.71);7.761(1.15);7.715(1.06);7.523(1.62);7.519(1.13);7.385(3.47);7.27(0.65);7.27(0.73);7.269(0.81);7.268(0.84);7.267(1.06);7.266(1.35);7.26(155.87);7.247(2);6.996(0.85);4.128(1.1);4.117(16);2.784(2.73);2.773(8.76);2.766(7.1);2.747(5.05);2.728(1.75);2.042(1.82);1.57(2.2);1.284(0.63);1.275(1.24);1.265(1.7);1.257(2.02);1.239(1.19);1.234(7.07);1.216(14.14);1.197(6.63);0.899(0.91);0.882(3.32);0.864(1.23);0.008(1.65);0.006(0.61);0.006(0.65);0.005(0.77);0(55.26);-0.006(0.8);-0.007(0.64);-0.008(1.72) Example 1-5: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.757(1);7.932(0.55);7.912(0.92);7.856(1.09);7.836(0.68);5.753(0.57);4.008(16);3.31(44.61);3.227(0.59);3.208(0.58);3.126(0.66);3.107(0.69);2.568(5.11);2.523(1.11);2.518(1.62);2.509(21.94);2.505(46.65);2.5(64.18);2.496(44.74);2.491(20.18);1.3(2.55);1.282(5.31);1.263(2.39);0(4.67) Example 1-6: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.826(0.98);8.065(0.55);7.964(0.9);7.944(0.68);7.914(0.63);7.778(1.36);7.641(0.65);4.022(16);3.542(0.71);3.524(2.42);3.506(2.48);3.488(0.75);3.309(87.5);2.742(8.48);2.669(0.56);2.523(1.92);2.509(34.37);2.505(72.77);2.5(99.75);2.496(69.83);2.491(31.46);2.327(0.57);1.267(2.62);1.248(5.94);1.23(2.62);0(3.28) Example 1-13: 1 H-NMR(400.0 MHz,CDCl3):δ=7.763(0.8);7.743(1.83);7.713(2.2);7.693(0.97);7.524(0.88);7.386(1.93);7.267(13.77);7.248(0.97);4.104(15.81);3.235(0.68);3.216(2.31);3.198(2.35);3.179(0.72);2.331(16);1.27(2.84);1.252(6.76);1.233(2.81);0(5.47) Example 1-14: 1H-NMR(400.0 MHz,d6-DMSO): δ=11.796(1.2);8.121(0.6);7.962(0.5);7.942(0.9);7.892(1.2);7.871(0.7);4.010(16.0);3.310(34.6);3.044(11.9);3.032(0.5);2.523(1.2);2.518(1.8);2.509(22.8);2.505(49.0);2.500(68.3);2.496(47.6);2.491(21.1);1.242(1.8);1.223(4.3);1.205(1.7);0.008(0.7);0.000(23.5);-0.009(0.7) Example 1-15: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.890(0.7);7.958(0.8);7.938(0.7);7.777(1.2);7.641(0.6);4.026(16.0);3.440(10.7);3.310(22.0);3.226(1.1);3.208(1.1);2.518(0.8);2.510(12.2);2.505(27.2);2.500(38.4);2.496(26.7);2.491(11.7);1.281(1.5);1.263(4.0);1.244(1.6);0.000(17.4) Example 1-16: 1 H-NMR(400.0 MHz,CDCl3):δ=7.792(0.77);7.772(1.59);7.735(2.01);7.715(0.98);7.537(0.8);7.399(1.81);7.261(16.53);5.298(1.09);4.119(16);3.253(0.59);3.234(2.01);3.216(2.06);3.197(0.64);2.797(1.14);2.778(3.65);2.76(3.69);2.741(1.19);1.258(4.01);1.239(8.35);1.228(2.65);1.221(4.02);1.21(6.13);1.191(2.52);0(6.53) Example 1-17: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.805(1.75);7.967(0.92);7.947(1.25);7.895(1.45);7.875(0.9);4.01(16);3.31(32.77);3.286(0.72);3.268(0.74);3.253(0.9);3.235(0.82);3.112(0.68);3.093(0.81);3.078(0.61);3.06(0.59);2.889(0.52);2.669(0.51);2.523(0.75);2.518(1.23);2.509(21.71);2.505(54.6);2.5(86.23);2.496(78.63);2.491(50.39);2.45(0.77);2.327(0.57);1.333(2.67);1.314(5.76);1.295(2.73);1.236(2.18);1.218(5.11);1.199(2.25);0.008(0.55);0(20.1) Example 1-18: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.893(0.71);7.984(0.74);7.963(0.58);7.907(0.53);7.771(1.23);7.634(0.63);4.026(16);3.512(0.62);3.494(2.16);3.475(2.18);3.457(0.67);3.31(42.94);3.208(1);3.19(0.97);2.523(0.75);2.518(1.2);2.51(21.1);2.505(47.16);2.5(66.67);2.496(46.4);2.491(20.66);2.45(0.51);1.276(2.41);1.267(1.83);1.257(5.73);1.249(4.46);1.239(2.59);1.231(1.78);0.008(0.64);0(25.34);-0.009(0.75) Example 1-25: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6077(1.3);7.6627(2.3);7.6435(0.5);7.5981(0.9);7.4606(2.0);7.3232(0.9);4.0382(16.0);3.3110(39.5);2.5224(1.2);2.5048(39.0);2.5004(50.9);2.4959(37.0);2.4915(18.2);2.4274(8.2);1.1329(0.5);1.1211(1.7);1.1177(1.7);1.0998(1.7);1.0850(0.6);0.6649(0.6);0.6508(2.0);0.6390(2.0);0.6247(0.5);-0.0002(8.8) Example 1-26: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.4191(0.9);8.2814(2.0);8.1437(1.0);7.9077(1.1);7.8874(1.8);7.8205(2.0);7.8004(1.3);4.0383(1.3);4.0204(1.6);4.0088(14.3);3.3113(10.0);3.0436(16.0);2.5229(1.6);2.5182(2.2);2.5095(22.6);2.5050(46.2);2.5005(62.8);2.4959(44.0);2.4914(20.3);2.0763(0.7);1.9878(5.4);1.2587(0.6);1.2366(2.5);1.1923(1.5);1.1745(3.0);1.1567(1.7);1.1286(0.8);1.1188(0.7);1.0038(0.6);0.9920(0.7);0.8539(0.5);0.7331(0.6);0.7162(1.5);0.7078(1.3);0.7015(1.4);0.6834(0.6);-0.0002(12.8) Example 1-27: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.7346(0.8);7.9246(0.7);7.8507(0.5);7.7145(1.3);7.5784(0.6);4.0346(16.0);3.5507(11.0);3.3125(58.4);2.5229(1.1);2.5095(18.7);2.5050(39.5);2.5004(54.9);2.4958(38.2);2.4913(17.4);1.9877(1.1);1.9079(0.9);1.1745(0.6);1.0897(1.0);1.0679(1.0);0.7579(1.0);0.7454(0.9);-0.0002(2.7) Example 1-28: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6295(0.9);7.6749(2.0);7.6085(0.8);7.4711(1.7);7.3336(0.8);4.0397(16.0);3.3095(63.0);2.9118(1.4);2.8935(1.4);2.8749(0.5);2.5229(0.8);2.5181(1.2);2.5094(19.5);2.5049(42.9);2.5003(60.3);2.4957(43.1);2.4912(20.1);1.1708(1.7);1.1525(3.4);1.1340(1.7);1.1148(1.4);1.1109(1.5);1.0992(0.8);1.0934(1.4);1.0896(1.4);0.6400(1.7);0.6288(1.6);-0.0002(13.9) Example 1-29: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6711(0.7);8.4143(0.8);8.2767(1.6);8.1391(0.9);7.9189(1.1);7.8985(1.7);7.8399(1.4);7.8198(0.9);4.0561(0.5);4.0382(2.1);4.0306(16.0);4.0206(1.8);4.0028(0.5);3.3099(19.0);3.1895(1.3);3.1721(1.8);3.1543(1.5);3.1366(0.5);2.5226(1.5);2.5092(20.9);2.5049(40.9);2.5004(54.3);2.4960(39.0);2.4917(19.0);1.9878(5.8);1.3407(2.8);1.3222(5.9);1.3036(2.7);1.1923(1.8);1.1746(3.4);1.1655(1.0);1.1568(2.0);1.0269(0.6);1.0145(0.8);0.7196(1.9);0.7058(2.0);0.6916(0.5);-0.0002(10.8) Example 1-30: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.7409(1.0);7.9943(0.8);7.9747(1.5);7.9399(2.1);7.9199(1.0);7.8511(0.9);7.7150(2.0);7.5793(1.0);4.0265(16.0);3.6682(1.0);3.6498(3.1);3.6313(3.2);3.6128(1.0);3.3090(28.7);2.6694(0.5);2.6176(0.7);2.5046(55.9);2.5003(70.6);2.4960(51.8);1.9877(1.9);1.3642(3.3);1.3458(7.0);1.3273(3.2);1.1923(0.5);1.1745(1.0);1.1567(0.5);1.0801(2.0);1.0586(1.9);0.7547(2.3);0.7425(2.2);-0.0002(13.0) Example 1-37: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.7857(1.1);7.9334(0.6);7.9140(0.8);7.8969(0.6);7.6578(1.1);7.6371(1.0);7.5220(0.6);7.3856(1.4);7.2492(0.6);3.9824(16.0);3.3115(48.1);2.5230(0.8);2.5184(1.1);2.5097(17.9);2.5051(39.4);2.5005(55.5);2.4959(39.4);2.4914(17.8);2.4735(7.9);-0.0002(14.1) Example 1-38: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.1061(0.8);8.0870(1.3);8.0692(1.0);7.8970(1.0);7.7721(1.8);7.7607(2.1);7.7520(1.7);7.6243(1.1);3.9297(16.0);3.3095(12.4);3.0901(13.2);2.6694(0.5);2.5228(1.8);2.5181(2.5);2.5094(28.2);2.5049(58.4);2.5004(80.0);2.4958(56.2);2.4913(26.2);0.0079(0.8);-0.0002(22.5);-0.0085(0.8) Example 1-39: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2804(0.9);8.2607(1.3);8.2433(1.0);7.9003(1.7);7.8796(1.6);7.8690(1.0);7.7327(2.1);7.5967(1.0);3.9669(16.0);3.5139(10.5);3.3104(80.6);3.1748(1.6);3.1619(1.6);2.6740(0.7);2.6694(0.9);2.6648(0.7);2.5228(3.8);2.5181(5.2);2.5094(52.7);2.5049(109.3);2.5003(150.0);2.4957(102.8);2.4911(46.4);2.3317(0.7);2.3271(0.9);2.3224(0.6);1.9876(0.6);1.9077(5.9);1.2361(0.8);0.0081(0.6);-0.0002(20.8);-0.0085(0.6) Example 1-40: 1 H-NMR(400.0 MHz,d6-DMSO): δ=7.9143(2.3);7.6397(2.7);7.6175(2.2);7.3770(2.8);3.9227(16.0);3.3088(54.4);2.9380(4.1);2.9203(3.9);2.9018(1.9);2.6694(1.7);2.5002(303.4);2.4959(221.2);2.3263(1.7);1.1770(4.2);1.1590(8.6);1.1410(4.3);-0.0002(77.2) Example 1-41: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.8887(1.1);8.0993(1.5);7.9430(1.0);7.8078(2.7);7.7950(1.7);7.6704(1.4);4.0555(1.1);4.0381(3.4);4.0203(3.6);4.0027(1.1);3.9461(9.2);3.4292(1.2);3.4110(1.4);3.3611(2.9);3.3468(3.1);3.3426(5.5);3.3096(2040.4);3.2729(2.1);3.2595(9.3);2.6785(3.9);2.6740(8.5);2.6693(11.7);2.6647(8.4);2.6600(3.9);2.6195(1.2);2.5612(4.2);2.5471(2.8);2.5228(44.4);2.5181(62.7);2.5094(668.3);2.5048(1388.2);2.5002(1912.9);2.4957(1320.7);2.4911(600.8);2.4649(3.8);2.4600(5.1);2.4553(6.7);2.4501(7.0);2.4056(1.2);2.3361(4.1);2.3316(8.3);2.3270(11.7);2.3224(8.5);2.0720(2.4);1.9876(16.0);1.9077(13.6);1.2530(3.9);1.2345(8.9);1.2165(3.8);1.1923(4.6);1.1745(9.3);1.1567(4.6);0.1458(1.8);0.0080(17.5);-0.0002(568.1);-0.0085(16.8);-0.0505(1.1);-0.1497(1.7) Example 1-42: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2076(1.1);7.8342(2.7);7.8051(2.4);7.7863(1.8);7.6979(5.2);7.5615(2.4);4.0559(1.0);4.0382(2.8);4.0203(2.8);4.0026(0.9);3.7961(8.4);3.5613(2.0);3.5428(5.2);3.5243(5.3);3.5076(2.1);3.4229(0.7);3.3778(1.0);3.3614(1.5);3.3443(2.7);3.3099(734.5);3.2789(1.7);3.2583(1.0);2.6740(4.1);2.6693(5.6);2.6646(4.1);2.6601(2.1);2.6302(0.7);2.5693(1.2);2.5227(24.1);2.5181(34.2);2.5094(325.9);2.5048(662.1);2.5003(900.8);2.4957(622.0);2.4912(282.5);2.4410(1.2);2.3316(3.7);2.3270(5.3);2.3224(3.7);2.1781(0.7);2.0719(0.8);1.9876(12.3);1.9073(7.0);1.2362(13.8);1.2240(16.0);1.2056(7.5);1.1923(4.2);1.1745(7.6);1.1567(3.7);1.1133(0.7);0.8539(1.6);0.8365(0.6);0.1459(0.7);0.0080(6.8);-0.0002(209.6);-0.0085(6.7);-0.1497(0.6) Example 1-49: 1H-NMR(400.0 MHz,d6-DMSO):δ=7.904(0.66);7.885(0.88);7.795(1.36);7.775(0.93);7.611(0.58);7.474(1.35);7.338(0.69);4.014(16);3.309(38.07);2.669(0.64);2.523(1.94);2.518(2.95);2.51(36.77);2.505(78.98);2.5(109.62);2.496(76.69);2.491(34.21);2.426(8.5);2.327(0.66);0(15.6) Example 1-50: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.958(0.9);8.2(0.6);8.063(1.32);8.045(0.8);8.01(1.29);7.926(0.68);4.01(16);3.305(22.19);3.097(8.07);2.669(0.94);2.522(2.77);2.518(4.06);2.509(59.83);2.505(130.08);2.5(181.46);2.495(127.32);2.491(58.04);2.327(1.11);0.008(3.08);0(89.77);-0.008(2.67) Example 1-51: 1 H-NMR(400.0 MHz,d6-DMSO):δ=12.036(0.97);8.194(0.61);8.074(1.13);8.053(0.84);7.94(0.6);7.803(1.34);7.666(0.7);4.028(16);3.571(8.8);3.301(23.52);2.674(0.75);2.669(1.08);2.664(0.74);2.55(0.55);2.522(3.09);2.518(4.34);2.509(58.23);2.504(126.06);2.5(175.99);2.495(123.31);2.49(55.64);2.456(0.51);2.331(0.76);2.326(1.05);2.322(0.76);0.008(0.69);0(26.33);-0.008(0.84) Example 1-52: 1 H-NMR(400.0 MHz,CDCl3):δ=7.775(3.97);7.772(3.32);7.47(0.93);7.332(2.04);7.26(29.31);7.195(0.99);4.144(16);2.963(0.81);2.944(2.5);2.926(2.59);2.907(0.99);1.257(3.42);1.239(6.98);1.22(3.25);1.216(0.8);0(12.32) Example 1-53: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.966(0.87);8.098(0.94);8.028(0.88);4.038(0.72);4.02(0.93);4.012(16);3.314(11.93);3.29(1.28);3.271(1.27);2.523(1.31);2.518(1.82);2.51(25.42);2.505(55.43);2.5(77.74);2.496(54.39);2.491(24.2);2.455(0.57);2.45(0.7);2.446(0.51);1.988(3.4);1.332(1.47);1.314(3.02);1.295(1.43);1.192(0.96);1.174(1.9);1.157(0.94);0.008(1.45);0(49.32);-0.008(1.5) Example 1-54: 1 H-NMR(400.0 MHz,d6-DMSO):δ=12.042(0.98);8.104(0.76);8.083(0.6);7.941(0.58);7.805(1.33);7.668(0.67);4.031(16);3.695(1.14);3.676(1.17);3.313(4.96);2.518(0.64);2.51(8.92);2.505(19.32);2.5(26.8);2.496(18.67);2.491(8.35);1.269(1.53);1.251(3.17);1.232(1.53);0(8.17) Example 1-61: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.891(0.6);7.845(0.74);7.834(1.19);7.623(0.51);7.486(1.18);7.349(0.58);4.04(16);3.309(17.41);2.523(0.93);2.518(1.43);2.509(20.81);2.505(45.5);2.5(63.89);2.496(44.28);2.491(19.4);2.45(0.57);2.422(4.44);0.008(1.2);0(45.19);-0.003(1.91);-0.004(0.69);-0.005(0.51);-0.008(1.3) Example 1-62: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.95(0.97);8.119(0.85);8.042(0.88);8.009(0.55);7.982(0.73);4.032(16);3.313(14.24);3.091(5.78);2.523(0.75);2.518(1.05);2.51(14.9);2.505(32.81);2.5(45.95);2.496(32.3);2.491(14.95);2.451(1.03);0.008(0.52);0(17.37);-0.008(0.58) Example 1-63: 1 H-NMR(400.0 MHz,d6-DMSO):δ=12.024(1.45);8.156(0.57);8.136(1.19);8.109(1.47);8.088(0.65);7.945(0.64);7.809(1.41);7.672(0.71);4.052(16);4.033(0.52);3.578(7.24);3.315(24.01);2.523(1.12);2.518(1.71);2.509(22.57);2.505(48.42);2.5(66.89);2.496(46.84);2.491(21.11);2.45(0.51);1.908(0.63);0(14.66) Example 1-64: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.895(0.69);7.847(1.98);7.623(0.63);7.487(1.38);7.35(0.67);4.039(16);3.31(24.78);2.947(1.27);2.929(1.29);2.523(1.32);2.518(1.97);2.51(25.95);2.505(55.92);2.5(77.48);2.496(53.77);2.491(23.63);2.45(0.51);1.18(1.52);1.162(3.05);1.143(1.55);0.008(1.65);0.005(0.58);0(57.33);-0.006(0.78);-0.007(0.67);-0.008(1.71) Example 1-65: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.952(1.03);8.144(0.84);8.072(0.51);8.051(0.95);8.008(0.74);5.754(6.01);4.03(16);3.312(32.93);3.29(0.97);3.273(1.14);3.255(1.07);3.238(0.51);2.523(0.84);2.518(1.19);2.51(23.97);2.505(54.05);2.5(76.85);2.496(55.23);2.491(26.33);2.448(1.56);2.327(0.52);1.358(1.55);1.34(3.27);1.321(1.6);0.008(0.63);0(29.26);-0.008(1.13) Example 1-66: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.024(2);8.178(0.76);8.158(1.87);8.135(2.05);8.115(0.84);7.945(0.94);7.809(2.09);7.673(1.03);4.052(16);4.032(0.78);3.736(0.8);3.718(2.2);3.699(2.26);3.681(0.89);3.408(8.24);2.523(1.56);2.518(2.34);2.51(28.84);2.505(61.43);2.501(84.52);2.496(58.95);2.492(26.44);2.451(0.53);2.327(0.52);1.908(2.96);1.285(2.36);1.266(4.74);1.248(2.44);0(13.92) Example 1-73: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.838(1.13);7.83(0.9);7.81(1.38);7.747(0.84);7.728(0.56);7.616(0.75);7.479(1.67);7.342(0.82);4.072(16);3.308(32.82);2.669(0.51);2.523(1.56);2.518(2.23);2.509(28.29);2.505(60.63);2.5(84.02);2.496(59.23);2.491(26.7);2.389(7.95);0.008(1.28);0(41.59);-0.008(1.17) Example 1-74: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.8934(2.0);8.3097(0.8);8.1727(1.5);8.0599(1.1);8.0377(1.5);7.8836(0.9);7.8618(0.7);4.0630(16.0);3.3137(92.6);3.0611(10.2);2.6739(0.8);2.6693(1.1);2.6649(0.8);2.5093(67.9);2.5048(133.1);2.5003(178.2);2.4958(128.5);2.4914(61.6);2.4668(0.9);2.3316(0.8);2.3271(1.0);2.3226(0.8);1.9078(1.0);0.0079(0.7);-0.0002(15.6) Example 1-75: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.9573(0.6);8.0873(0.6);8.0668(0.8);8.0024(0.8);7.7909(0.6);4.6702(16.0);4.0858(3.6);3.7444(0.6);3.7272(0.6);3.5478(3.4);2.5073(63.7);1.1028(1.1);1.0860(0.6);-0.0002(7.0) Example 1-76: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.845(1.1);7.845(1.01);7.824(1.49);7.752(0.93);7.732(0.73);7.621(0.84);7.484(1.79);7.347(0.91);4.072(16);3.309(22.23);2.934(0.71);2.916(1.87);2.898(1.91);2.879(0.72);2.523(1.04);2.51(23.62);2.505(50.6);2.5(69.98);2.496(49.39);2.492(22.64);1.201(2.17);1.182(4.37);1.164(2.23);0.008(0.79);0(25.78);0(26.27);-0.008(0.89) Example 1-77: 1H-NMR(400.6 MHz,d6-DMSO):δ=11.907(1.26);8.316(0.51);8.179(1.11);8.066(1);8.045(1.52);7.889(0.71);7.87(0.59);4.062(16);3.322(71.9);3.271(0.71);3.253(0.65);3.22(0.94);3.201(1);3.186(0.58);2.524(1.42);2.519(1.95);2.51(18.46);2.506(38.47);2.501(53.07);2.497(37.86);2.492(17.47);1.908(0.81);1.392(2.57);1.374(5.24);1.355(2.46);0(2.75) Example 1-78: 1 H-NMR(400.6 MHz,d6-DMSO): δ=11.9547(3.0);8.1145(1.7);8.0944(2.4);8.0249(2.0);8.0044(1.4);7.9278(1.3);7.7916(2.8);7.6554(1.4);4.0838(16.0);4.0628(1.2);3.7147(1.3);3.6968(3.4);3.6786(3.4);3.6603(1.3);3.3498(1.4);3.3246(83.1);2.5054(50.1);2.5012(64.4);2.4972(49.3);1.3078(3.6);1.2898(7.0);1.2718(3.6);-0.0002(1.0) Example 2-1: 1H-NMR(400.0 MHz,CDCl3):δ=7.782(0.64);7.762(1.18);7.717(1.18);7.697(0.67);7.518(0.55);7.504(0.93);7.366(2.07);7.26(99.7);7.228(1.08);6.996(0.53);4.505(1.09);4.487(3.51);4.469(3.55);4.451(1.15);2.795(8.78);2.306(16);1.655(4);1.637(8.77);1.619(3.98);0.008(1.1);0(41.08);-0.008(1.35) Example 2-2: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.653(1.38);7.996(0.99);7.913(0.74);7.893(1.22);7.858(0.61);7.843(1.5);7.823(0.84);4.381(1.22);4.362(3.94);4.344(4.01);4.326(1.24);3.308(63.88);3.004(16);2.674(0.83);2.669(1.17);2.665(0.79);2.588(9.37);2.523(4.05);2.518(5.99);2.509(67.99);2.505(144.81);2.5(198.98);2.496(137.97);2.491(61.37);2.332(0.8);2.327(1.2);2.322(0.85);1.495(4.44);1.476(10.14);1.458(4.38);0.008(1.03);0(33.01);-0.008(1) Example 2-3: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.725(2.33);8.062(0.79);8.04(0.99);7.94(1.78);7.92(2.29);7.784(2.61);7.648(1.23);4.396(1.93);4.378(6.18);4.36(6.2);4.342(1.93);3.953(0.62);3.448(22.11);3.307(82.43);2.749(16);2.678(0.56);2.674(1.21);2.669(1.7);2.665(1.21);2.66(0.6);2.554(0.74);2.55(1.08);2.545(1.09);2.54(1.19);2.523(5.51);2.518(7.94);2.509(97.61);2.505(210.76);2.5(294.34);2.496(205.42);2.491(91.2);2.449(0.56);2.444(0.58);2.336(0.6);2.332(1.32);2.327(1.73);2.322(1.25);2.318(0.64);1.499(6.55);1.488(0.97);1.481(15.03);1.463(6.47);0.008(1.61);0(55.05);-0.008(1.58) Example 2-4: 1H-NMR(400.0 MHz,CDCl3):δ=7.734(1.82);7.713(1.8);7.523(1.88);7.518(1.48);7.385(4.08);7.259(231.31);7.247(2.6);6.995(1.28);5.298(2.5);4.501(1.83);4.483(5.75);4.464(5.86);4.446(2);2.781(3.06);2.771(12.83);2.763(7.54);2.744(6.31);2.726(2.13);2.042(1.22);1.657(6.23);1.639(13.17);1.62(6.2);1.549(2.26);1.331(0.56);1.284(0.96);1.275(0.87);1.258(2.45);1.234(7.93);1.215(16);1.197(7.45);0.882(1.4);0.864(0.65);0.008(3.22);0(94.1);-0.008(2.86) Example 2-5: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.658(2.62);8.018(0.79);7.923(1.2);7.902(2.04);7.857(2.63);7.837(1.41);5.753(0.64);4.381(2.1);4.363(6.57);4.345(6.61);4.326(2.09);3.36(1.48);3.31(147.53);3.242(1.06);3.227(1.35);3.208(1.25);3.127(1.46);3.108(1.59);3.094(1.02);3.075(0.93);2.674(1.24);2.669(1.68);2.665(1.25);2.566(12.77);2.55(3.76);2.523(9.33);2.518(11.63);2.509(91.56);2.505(188.98);2.5(258.72);2.496(182.09);2.491(83.39);2.439(0.56);2.336(0.58);2.332(1.13);2.327(1.54);2.322(1.05);1.494(7.27);1.476(16);1.458(7.09);1.301(5.62);1.283(11.89);1.264(5.31);0(11.34) Example 2-6: 1 H-NMR(400.0 MHz,CDCl3):δ=7.971(1);7.952(3.22);7.922(1.79);7.902(0.79);7.814(2.84);7.676(1.43);7.518(1.29);7.259(209.94);6.995(1.08);4.515(1.03);4.496(2.82);4.478(2.89);4.46(1.07);3.345(1.6);3.326(4.87);3.307(5);3.288(1.56);2.869(16);1.66(4.56);1.642(9.29);1.624(4.63);1.565(0.98);1.446(5.4);1.428(11.03);1.409(5.05);1.33(1);1.284(1.24);1.255(1.35);0.008(2.95);0(83.48);-0.008(3.21) Example 2-13:1 H-NMR(400.0 MHz,CDCl3):δ=7.776(0.71);7.756(1.67);7.728(2.13);7.708(0.9);7.522(0.87);7.384(1.93);7.26(26.96);7.246(0.99);4.513(1.12);4.494(3.67);4.476(3.7);4.458(1.16);3.234(0.66);3.215(2.22);3.196(2.25);3.178(0.69);2.331(16);2.279(1.29);1.653(3.97);1.634(8.64);1.616(3.91);1.259(2.77);1.24(6.6);1.222(2.76);0(11.06) Example 2-14: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.692(1.42);8.122(0.85);7.95(0.61);7.93(1.17);7.892(1.62);7.872(0.8);4.382(1.13);4.364(3.67);4.345(3.75);4.327(1.17);3.36(0.71);3.31(123.1);3.045(16);3.028(0.59);2.884(0.58);2.867(0.51);2.674(0.59);2.669(0.84);2.665(0.59);2.555(0.52);2.551(0.65);2.523(2.39);2.518(3.56);2.51(49.94);2.505(108.7);2.5(152.09);2.496(105.57);2.491(46.48);2.45(0.52);2.332(0.71);2.327(0.99);2.323(0.68);1.496(4.41);1.478(10.45);1.46(4.34);1.243(2.28);1.224(5.68);1.206(2.3);0.008(1.4);0(53);-0.008(1.59) Example 2-15: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.786(2.88);8.099(0.76);8.079(0.95);7.961(1.95);7.941(1.51);7.914(1.19);7.778(2.66);7.641(1.33);4.398(1.87);4.38(6.21);4.362(6.32);4.344(1.99);3.442(23.78);3.31(71.85);3.26(0.53);3.243(0.81);3.224(2.56);3.206(2.61);3.188(0.82);2.674(0.55);2.669(0.78);2.665(0.57);2.523(2.17);2.518(3.27);2.509(46.2);2.505(100.26);2.5(140.15);2.496(97.51);2.491(43.24);2.455(0.96);2.45(1.19);2.446(0.82);2.332(0.66);2.327(0.9);2.322(0.66);1.508(6.92);1.49(16);1.471(6.85);1.283(3.68);1.265(9.36);1.246(3.68);0.008(1.44);0(52.54);-0.009(1.58) Example 2-16: 1H-NMR(400.0 MHz,CDCl3):δ=7.697(13.47);7.536(1.83);7.519(0.89);7.398(4.27);7.26(151.86);7.21(1.21);6.996(0.85);5.299(2.93);4.495(1.8);4.476(5.74);4.458(5.82);4.44(1.87);3.234(1.21);3.215(4.19);3.196(4.29);3.178(1.36);2.791(2.11);2.773(6.77);2.754(6.92);2.736(2.25);1.649(6.3);1.63(13.48);1.612(6.48);1.562(1.18);1.258(7.71);1.239(16);1.23(4.76);1.221(7.78);1.211(10.55);1.192(4.55);0.008(1.64);0(62.7);-0.008(2.04);-0.05(0.51) Example 2-17: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.702(3.4);8.105(0.58);7.957(1.15);7.938(1.79);7.898(2.55);7.878(1.29);4.384(1.92);4.366(6.16);4.348(6.2);4.329(1.96);3.408(4.77);3.287(1.05);3.269(1.21);3.254(1.57);3.236(1.45);3.115(1.21);3.096(1.34);3.081(1.01);3.063(0.95);3.003(0.58);2.91(0.6);2.892(0.74);2.873(0.59);2.67(0.57);2.523(2.07);2.518(2.96);2.51(34.26);2.505(73.09);2.5(100.87);2.496(71.3);2.491(32.71);2.455(0.85);2.45(0.95);2.446(0.67);2.327(0.65);1.498(6.96);1.48(16);1.462(6.95);1.334(5.11);1.316(11.02);1.297(4.99);1.238(4.02);1.22(9.38);1.201(3.94);1.097(0.51);0.008(1.4);0(46.28);-0.008(1.61) Example 2-25: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.4970(5.3);7.6651(5.7);7.5989(1.8);7.4617(4.1);7.3241(2.0);4.4055(2.5);4.3875(7.8);4.3694(7.9);4.3512(2.6);3.3109(92.1);2.6700(0.7);2.5048(90.3);2.5004(124.7);2.4960(95.3);2.4277(17.1);2.3269(0.8);2.2239(1.1);1.5140(7.4);1.4960(16.0);1.4778(7.4);1.1276(1.2);1.1124(3.9);1.0906(3.8);0.6604(4.2);0.6483(4.2);-0.0002(20.4) Example 2-26: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.5506(0.6);8.4204(0.9);8.2828(2.0);8.1452(1.0);7.9244(1.2);7.9043(1.8);7.8322(1.3);7.8122(0.9);4.3953(1.4);4.3771(4.5);4.3590(4.6);4.3408(1.5);3.3111(15.5);3.0501(16.0);2.5228(1.4);2.5180(2.0);2.5094(19.3);2.5049(39.1);2.5004(52.9);2.4959(37.0);2.4914(17.0);2.0912(0.6);1.5076(5.0);1.4895(10.9);1.4714(4.8);1.1359(0.9);1.1262(0.7);1.0041(0.7);0.9916(0.8);0.7379(0.6);0.7226(1.7);0.7149(1.4);0.7073(1.6);0.6910(0.6);-0.0002(9.7) Example 2-27: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6185(0.9);7.9585(0.6);7.9220(1.3);7.9027(0.7);7.8503(0.8);7.7148(1.8);7.5785(0.9);4.3976(1.2);4.3794(4.0);4.3612(4.0);4.3430(1.3);3.5516(16.0);3.3127(55.9);2.6691(0.6);2.5230(1.4);2.5182(2.1);2.5095(24.1);2.5050(50.8);2.5004(70.5);2.4959(49.0);2.4913(22.3);1.9877(0.8);1.5026(4.5);1.4845(10.3);1.4663(4.4);1.0834(1.6);1.0612(1.5);0.7677(1.4);0.7550(1.4);-0.0002(3.4) Example 2-28: 1H-NMR(400.0 MHz,d6-DMSO): δ=11.5133(0.9);7.6696(7.3);7.6086(1.6);7.4711(3.7);7.3337(1.8);4.4020(2.1);4.3838(6.9);4.3657(7.0);4.3475(2.2);4.1051(0.8);4.0870(0.8);3.3107(89.4);2.9283(1.4);2.9099(4.2);2.8915(4.3);2.8731(1.5);2.6696(0.7);2.6651(0.5);2.5502(0.6);2.5231(1.9);2.5184(2.7);2.5097(38.7);2.5051(85.2);2.5005(119.6);2.4959(85.2);2.4913(39.3);2.3319(0.5);2.3273(0.7);2.3227(0.5);2.1684(0.6);1.9878(1.2);1.5132(7.1);1.4950(16.0);1.4769(7.1);1.3132(1.0);1.2951(2.0);1.2770(0.9);1.2364(1.2);1.1745(1.2);1.1681(5.3);1.1497(11.0);1.1313(5.2);1.1173(1.1);1.1054(2.8);1.1016(2.9);1.0963(1.6);1.0900(1.5);1.0843(2.8);1.0803(2.9);1.0689(1.0);0.6665(1.0);0.6517(3.6);0.6406(3.3);0.6373(2.9);0.6256(0.9);-0.0002(8.6) Example 2-29: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.5628(0.8);8.4128(1.7);8.2753(3.1);8.1370(1.8);7.9186(2.3);7.8975(3.2);7.8340(2.4);7.8130(1.5);4.3916(2.3);4.3734(6.9);4.3552(6.6);4.3371(2.1);4.1055(0.8);4.0382(1.1);4.0207(1.0);3.3124(98.0);3.2069(1.2);3.1884(2.6);3.1736(3.0);3.1554(2.7);2.6694(1.0);2.5095(67.8);2.5051(133.9);2.5006(178.2);2.4961(126.0);2.4917(59.2);2.3274(1.1);2.0454(1.2);1.9879(4.6);1.9077(1.2);1.5063(7.3);1.4883(16.0);1.4701(7.4);1.3408(5.8);1.3223(12.3);1.3038(6.0);1.2363(2.7);1.1924(1.4);1.1746(3.0);1.1569(2.7);0.9953(1.7);0.7284(3.6);0.7134(3.5);-0.0002(8.2) Example 2-30: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6232(1.1);7.9885(0.7);7.9676(1.4);7.9403(2.8);7.9201(1.2);7.8509(1.3);7.7150(3.1);7.5792(1.5);4.3930(1.9);4.3749(6.1);4.3567(6.2);4.3386(1.9);4.0382(1.0);4.0205(1.0);3.6699(1.4);3.6515(4.9);3.6330(5.0);3.6145(1.5);3.3090(61.8);2.6739(0.6);2.6693(0.8);2.6647(0.6);2.6166(0.7);2.5228(3.1);2.5181(4.2);2.5094(43.8);2.5048(90.9);2.5003(124.8);2.4957(86.5);2.4911(39.4);2.3316(0.5);2.3270(0.7);2.3224(0.5);1.9877(4.5);1.4994(7.1);1.4813(16.0);1.4631(6.9);1.3647(5.2);1.3463(11.9);1.3277(5.1);1.2477(0.9);1.1923(1.3);1.1745(2.5);1.1568(1.2);1.0902(0.7);1.0789(2.4);1.0755(2.4);1.0572(2.3);1.0538(2.4);1.0432(0.8);0.8584(1.6);0.8408(0.5);0.7623(2.6);0.7504(2.6);0.0080(1.1);-0.0002(34.1);-0.0085(1.0) Example 2-37: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.6992(0.6);7.9256(1.4);7.9063(2.0);7.8890(1.6);7.6505(2.7);7.6303(2.4);7.5208(1.3);7.3840(3.2);7.2476(1.4);4.3607(2.0);4.3424(6.3);4.3242(6.3);4.3061(2.1);3.3121(54.1);2.6698(0.6);2.5231(2.1);2.5184(3.1);2.5098(40.3);2.5052(87.1);2.5006(121.2);2.4961(85.1);2.4915(38.2);2.4692(18.3);2.3273(0.6);1.4797(7.2);1.4615(16.0);1.4434(7.1);0.0081(0.7);-0.0002(24.4) Example 2-38: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.1029(1.1);8.0835(1.7);8.0657(1.1);7.8972(1.3);7.7619(3.8);7.7439(1.9);7.6243(1.4);4.3200(1.4);4.3019(4.2);4.2837(4.3);4.2656(1.5);4.0383(1.5);4.0205(1.5);3.3104(14.2);3.0864(16.0);2.6696(0.6);2.5353(0.6);2.5229(2.5);2.5183(3.4);2.5096(38.0);2.5050(79.6);2.5004(109.8);2.4959(77.0);2.4913(35.5);2.3273(0.6);1.9877(7.0);1.9077(4.3);1.4529(4.7);1.4348(10.1);1.4166(4.7);1.2363(1.3);1.1923(1.9);1.1745(3.9);1.1567(1.9);0.0080(0.9);-0.0002(30.6);-0.0085(1.0) Example 2-39: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2399(2.3);8.2215(3.8);8.2023(2.3);7.8493(2.4);7.8165(4.9);7.7959(4.4);7.7127(4.9);7.5765(2.4);4.2684(3.2);4.2503(9.0);4.2322(9.1);4.2142(3.5);3.4864(25.8);3.3109(31.8);3.1687(2.0);2.6693(1.3);2.5044(158.8);2.5004(191.6);2.4964(145.5);2.3270(2.5);1.9075(2.4);1.4240(8.0);1.4060(16.0);1.3879(8.9);1.2988(1.5);1.2589(1.9);1.2365(5.0);0.8541(0.8);-0.0002(32.4) Example 2-40: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.7204(1.7);7.9359(2.4);7.9183(3.8);7.9009(2.4);7.6571(4.5);7.6372(3.7);7.5194(2.3);7.3838(4.3);7.2484(2.0);4.3409(2.6);4.3242(7.4);4.3051(7.4);4.2869(2.8);3.3090(49.0);2.9597(2.2);2.9413(6.4);2.9230(6.8);2.9038(2.8);2.6687(1.9);2.5002(293.9);2.3271(1.8);1.4679(7.5);1.4498(16.0);1.4313(8.1);1.2334(1.6);1.1775(7.4);1.1591(14.7);1.1410(8.1);-0.0002(78.4) Example 2-41: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.1068(2.0);8.0885(3.3);8.0698(2.0);7.9403(2.4);7.8377(0.6);7.8038(5.2);7.7669(4.1);7.7464(3.5);7.7057(0.6);7.6674(2.6);4.2904(2.6);4.2722(7.4);4.2540(7.7);4.2360(2.8);4.0383(1.4);4.0206(1.4);3.5519(0.6);3.5341(0.6);3.3104(49.0);3.2792(3.9);3.2512(2.9);3.2323(2.8);3.2173(1.8);3.1990(1.3);3.1815(0.6);2.6740(1.2);2.6695(1.5);2.5092(104.5);2.5050(194.7);2.5005(250.3);2.4961(176.6);2.4918(84.2);2.3314(1.1);2.3272(1.4);2.3227(1.1);1.9877(6.1);1.4341(7.8);1.4160(16.0);1.3978(8.2);1.2987(0.9);1.2586(2.0);1.2455(8.4);1.2362(6.9);1.2272(15.5);1.2087(7.9);1.1924(2.6);1.1746(3.6);1.1568(1.8);0.8540(0.8);0.0078(2.7);-0.0002(52.5);-0.0084(2.4) Example 2-42: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2767(1.8);8.2576(2.9);8.2395(1.9);7.8731(3.6);7.8514(4.7);7.7140(4.1);7.5779(2.0);4.3036(2.2);4.2854(6.8);4.2673(7.0);4.2491(2.6);4.0383(1.1);4.0205(1.1);3.5835(1.8);3.5649(5.2);3.5465(5.4);3.5283(2.1);3.3105(19.4);2.6741(0.8);2.6695(1.2);2.6649(0.9);2.5391(0.6);2.5230(4.3);2.5183(6.0);2.5096(65.2);2.5051(136.3);2.5005(187.8);2.4959(130.6);2.4913(60.0);2.4746(0.6);2.4695(0.6);2.4647(0.6);2.3319(0.8);2.3273(1.1);2.3226(0.8);1.9877(5.3);1.9077(5.4);1.4445(6.8);1.4264(14.1);1.4083(7.1);1.3757(0.8);1.3568(0.6);1.2986(0.8);1.2523(7.0);1.2342(16.0);1.2155(7.0);1.1923(1.9);1.1791(0.6);1.1745(3.3);1.1567(1.6);0.8539(0.8);0.0079(2.0);0.0063(0.9);0.0054(0.9);-0.0002(60.8);-0.0068(0.8);-0.0085(1.9) Example 2-49: 1 H-NMR(400.0 MHz,CDCl3): δ=7.764(6.0);7.519(0.6);7.449(1.5);7.312(3.2);7.288(0.6);7.281(0.7);7.274(1.0);7.270(1.1);7.261(99.8);7.253(0.8);7.238(1.0);7.184(0.8);7.175(1.8);6.997(0.5);4.533(1.4);4.515(4.3);4.497(4.4);4.479(1.5);2.434(16.0);2.356(2.5);1.658(5.4);1.639(11.0);1.621(5.6);1.599(1.1);0.008(1.1);0.000(31.9);-0.008(0.9) Example 2-50: 1 H-NMR(400.0 MHz,CDCl3):δ=8.132(0.89);8(1.75);7.992(1.3);7.983(1.51);7.902(1.89);7.882(1.32);7.858(1.04);7.519(1.68);7.312(0.71);7.31(0.84);7.26(298.81);7.25(2.51);7.246(1.94);7.245(1.75);7.238(1.35);7.235(1.24);7.23(1.29);7.226(1.19);7.212(1.82);7.21(2.71);6.996(1.68);4.516(0.77);4.498(2.34);4.479(2.42);4.462(0.94);3.491(3.07);3.113(16);1.65(4.71);1.632(9.95);1.613(5.13);1.581(1.19);1.284(0.54);1.264(0.51);0.008(3.84);0.006(1.8);0(131.12);-0.006(2.66);-0.007(2.35);-0.008(4.88);-0.012(1.21);-0.014(1.02);-0.015(1);-0.016(0.93);-0.016(0.92);-0.023(0.72);-0.031(0.65);-0.034(0.59);-0.049(0.89);-0.05(1.13) Example 2-51: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.958(4.87);8.222(1.31);8.204(1.63);8.08(2.62);8.06(2.11);7.941(1.46);7.805(3.15);7.668(1.59);4.415(2.72);4.397(8.24);4.378(8.39);4.36(2.91);3.578(16);3.322(26.13);2.6(0.51);2.51(30.41);2.505(58.09);2.501(76.3);2.496(56.56);2.492(29.5);2.376(0.86);2.328(0.51);1.908(0.61);1.503(7.09);1.485(14.54);1.467(7.11);0(5.05) Example 2-52: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.815(4.01);7.914(0.97);7.894(1.25);7.818(2.55);7.798(1.69);7.613(1.3);7.477(2.89);7.341(1.5);4.406(2.74);4.388(8.88);4.369(9);4.351(2.81);3.312(50.97);2.968(1.01);2.949(2.73);2.931(2.85);2.913(1.15);2.674(0.97);2.67(1.36);2.665(1.01);2.523(3.6);2.518(5.5);2.51(74.19);2.505(159.44);2.5(220.37);2.496(153.51);2.491(68.91);2.455(1.13);2.45(1.5);2.446(1.22);2.332(1);2.327(1.36);2.323(0.97);1.501(7.28);1.483(16);1.464(7.26);1.172(3.24);1.153(6.44);1.135(3.27);1.124(0.96);0.008(1.66);0(55.84);-0.008(1.75) Example 2-53: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.8750(1.0);8.2361(1.6);8.0993(3.4);8.0449(1.3);8.0259(3.8);8.0088(3.9);7.9895(1.2);7.9615(1.8);4.3757(1.5);4.3582(4.2);4.3400(4.2);4.3230(1.5);4.0382(1.0);4.0205(1.2);3.3098(43.4);3.2858(6.5);3.2671(6.4);3.2486(2.4);2.6696(1.3);2.5229(4.3);2.5183(6.1);2.5095(73.4);2.5050(154.6);2.5004(215.2);2.4958(148.1);2.4912(66.6);2.3272(1.3);1.9877(4.9);1.4810(6.8);1.4630(14.4);1.4448(6.4);1.3330(7.3);1.3143(16.0);1.2958(7.0);1.1924(1.4);1.1745(2.6);1.1567(1.4);0.0080(2.8);-0.0002(81.0);-0.0086(2.2) Example 2-54: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.942(2);8.228(1.01);8.207(1.26);8.097(2.84);8.076(2.1);7.94(1.56);7.804(3.52);7.668(1.78);4.409(2.5);4.391(8.06);4.373(8.18);4.355(2.57);4.019(0.52);3.713(1.22);3.695(3.77);3.676(3.8);3.658(1.26);3.359(0.55);3.309(140.03);2.679(0.52);2.674(1.09);2.669(1.55);2.665(1.11);2.66(0.51);2.55(0.99);2.546(0.9);2.523(4.38);2.518(6.36);2.509(88.23);2.505(190);2.5(264.68);2.496(187.05);2.491(85.07);2.336(0.55);2.332(1.15);2.327(1.58);2.322(1.12);2.318(0.52);1.908(1.85);1.5(7.27);1.482(16);1.464(7.18);1.269(4.93);1.251(10.54);1.232(4.85);0.008(0.63);0(21.63);-0.008(0.63) Example 2-61: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.789(0.78);7.832(4.59);7.624(1.36);7.488(3.17);7.351(1.57);4.425(2.21);4.407(7.28);4.389(7.44);4.371(2.36);3.313(44.01);2.67(0.6);2.523(1.36);2.518(1.97);2.51(31.73);2.505(70.06);2.501(98.7);2.496(68.26);2.491(29.74);2.455(0.71);2.451(0.9);2.446(0.73);2.423(13.86);2.327(0.66);2.323(0.54);1.506(7.04);1.488(16);1.477(0.88);1.47(7.03);1.295(0.67);0.008(1.25);0(53.01);-0.009(1.52) Example 2-62: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.848(1.55);8.258(0.92);8.12(1.77);8.058(1.16);8.038(2.12);7.993(1.36);7.983(1.5);7.974(0.79);4.411(1.93);4.393(6.15);4.375(6.27);4.357(1.93);3.311(34.49);3.092(16);2.674(0.61);2.67(0.82);2.665(0.6);2.523(2.33);2.518(3.43);2.51(46.02);2.505(100.05);2.5(138.84);2.496(96.41);2.491(42.71);2.455(0.73);2.45(0.99);2.446(0.72);2.332(0.63);2.327(0.89);2.323(0.63);1.498(6.39);1.488(0.97);1.48(14.61);1.462(6.34);0.008(1.18);0(40.28);-0.009(1.17) Example 2-63: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.914(5.85);8.15(1.2);8.13(2.85);8.108(3.49);8.087(1.51);7.945(1.55);7.81(3.19);7.673(1.6);4.434(3.14);4.416(10.37);4.398(10.6);4.379(3.5);3.581(16);3.313(71.82);3.263(0.56);3.094(0.55);2.674(1.08);2.669(1.51);2.665(1.14);2.544(0.83);2.533(0.85);2.523(4.25);2.518(6.48);2.509(87.05);2.505(187.69);2.5(260.68);2.496(183.67);2.491(83.21);2.455(1.32);2.45(1.82);2.446(1.48);2.332(1.2);2.327(1.64);2.322(1.21);2.072(0.73);1.908(1.31);1.509(7.03);1.491(14.66);1.473(6.98);0.008(1.03);0(32.97);-0.009(1.01) Example 2-64: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.796(3.41);7.845(5.27);7.625(1.35);7.488(3.09);7.352(1.52);4.425(2.64);4.407(8.62);4.388(8.82);4.37(2.87);3.313(85.07);3.281(0.78);3.262(1.54);2.967(1);2.949(2.87);2.931(2.97);2.913(1.17);2.674(0.67);2.67(0.96);2.665(0.65);2.523(2.38);2.518(3.4);2.51(52.5);2.505(116.35);2.501(163.67);2.496(116.08);2.491(54.4);2.451(3.76);2.332(0.79);2.327(1.09);2.323(0.81);1.506(7.17);1.488(16);1.47(7.33);1.182(3.23);1.164(6.44);1.145(3.41);0.008(1.54);0(58.7);-0.008(2.17);-0.05(0.55) Example 2-65: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.851(3.1);8.281(0.9);8.144(2.02);8.07(1.29);8.05(2.28);8.007(2.18);7.987(0.74);5.753(3.48);4.412(2.63);4.394(8.03);4.376(8.01);4.358(2.49);3.308(51.28);3.292(1.78);3.274(2.42);3.256(2.06);3.238(0.73);2.674(0.84);2.669(1.13);2.665(0.81);2.523(3.61);2.518(5.24);2.509(62.91);2.505(134.1);2.5(185.44);2.496(128.96);2.491(57.39);2.332(0.81);2.327(1.13);2.322(0.77);1.498(7.2);1.48(16);1.462(7.08);1.36(3.86);1.342(7.87);1.323(3.7);0.008(1.31);0(44.58);-0.009(1.27) Example 2-66: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.907(6.58);8.148(3.05);8.132(4.16);8.111(1.56);7.946(2.21);7.809(4.95);7.673(2.56);5.753(3.58);4.431(4.08);4.413(12.83);4.395(13.14);4.377(4.33);3.736(1.64);3.718(4.27);3.7(4.27);3.682(1.67);3.308(154.84);2.674(2.34);2.669(3.29);2.664(2.34);2.605(0.68);2.6(0.69);2.596(0.52);2.523(11.08);2.518(16.52);2.509(186.01);2.505(391.83);2.5(538.2);2.496(378.66);2.491(170.21);2.405(0.58);2.401(0.55);2.336(1.18);2.332(2.34);2.327(3.22);2.322(2.24);2.072(0.74);1.507(7.73);1.489(16);1.471(7.64);1.285(4.92);1.268(9.62);1.249(5.24);0.008(3.72);0(118.16);-0.008(3.62) Example 2-73: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.7312(2.7);7.8291(1.6);7.8091(2.3);7.7295(1.2);7.7094(0.9);7.6171(1.2);7.4801(2.7);7.3432(1.4);4.4651(1.8);4.4469(5.8);4.4287(5.8);4.4106(1.9);4.1047(1.2);4.0866(1.2);3.3096(124.1);2.6740(0.8);2.6694(1.2);2.6648(0.8);2.5396(1.0);2.5229(4.2);2.5182(5.7);2.5095(67.9);2.5049(143.6);2.5003(198.8);2.4958(137.4);2.4912(62.6);2.4282(0.5);2.3895(14.3);2.3318(0.9);2.3271(1.2);2.3225(0.9);2.0724(1.2);1.5146(7.0);1.4965(16.0);1.4784(7.0);1.3127(1.3);1.2947(2.7);1.2765(1.2);-0.0002(1.4) Example 2-75: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.8398(0.9);8.0607(1.6);8.0404(2.3);7.9492(1.5);7.9288(1.3);7.7868(2.0);7.6505(1.0);4.4498(1.0);4.4316(3.1);4.4135(3.2);4.3954(1.1);3.5447(16.0);3.3082(73.5);2.6738(0.7);2.6693(1.0);2.6645(0.7);2.5225(4.7);2.5178(6.5);2.5091(57.0);2.5047(114.6);2.5001(153.9);2.4956(107.8);2.4911(49.8);2.3315(0.6);2.3269(0.9);1.9076(0.6);1.5032(4.2);1.4851(9.3);1.4670(4.2);0.0079(1.0);-0.0002(22.9);-0.0085(0.8) Example 2-76: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.734(3.5);7.845(1.51);7.825(2.18);7.736(1.27);7.719(1);7.622(1.21);7.485(2.66);7.348(1.31);4.465(1.85);4.447(5.86);4.429(5.95);4.411(1.97);3.31(15.7);2.935(1.05);2.917(3.01);2.898(3.1);2.88(1.08);2.523(1.13);2.518(1.54);2.51(27.58);2.505(60.79);2.5(85.15);2.496(59.71);2.491(26.86);1.516(7.27);1.497(16);1.479(7.16);1.202(3.41);1.184(6.77);1.165(3.3);0.008(1.06);0(37.76);-0.009(1) Example 2-77: 1H-NMR(400.6 MHz,d6-DMSO):δ=11.804(3.11);8.317(0.87);8.18(1.85);8.065(1.77);8.044(2.97);7.875(1.2);7.856(1);5.756(2.22);4.45(2.21);4.432(6.58);4.414(6.53);4.396(2.09);3.371(0.61);3.348(0.8);3.344(0.92);3.321(147.23);3.3(1.36);3.295(0.98);3.274(1.21);3.256(1.09);3.238(0.85);3.22(1.62);3.202(1.7);3.187(0.99);3.168(0.77);2.674(0.56);2.67(0.77);2.665(0.53);2.524(3.93);2.519(5.79);2.51(47.64);2.506(96.69);2.501(130.94);2.496(91.41);2.492(40.65);2.48(1.21);2.476(0.93);2.333(0.56);2.328(0.78);2.324(0.53);1.908(1.8);1.508(7.33);1.49(16);1.472(7.12);1.394(4.4);1.375(8.88);1.357(4.11);0.008(0.79);0(21.3);-0.009(0.63) Example 2-78: 1 H-NMR(400.6 MHz,d6-DMSO): δ=11.8469(6.1);8.1145(2.7);8.0943(3.8);8.0140(3.3);7.9939(2.3);7.9290(2.0);7.7926(4.4);7.6569(2.2);4.4720(2.6);4.4539(7.6);4.4358(7.6);4.4177(2.6);3.7188(1.9);3.7008(5.1);3.6822(5.2);3.6641(1.9);3.3760(1.3);3.3530(2.2);3.3273(264.9);3.2765(0.5);2.6701(0.7);2.5237(3.8);2.5105(42.7);2.5060(87.1);2.5014(118.0);2.4969(83.3);2.4924(37.8);2.3332(0.5);2.3286(0.7);1.5170(7.8);1.4989(16.0);1.4808(7.7);1.3113(5.4);1.2930(10.6);1.2746(5.3);-0.0002(2.2) Example 3-1: 1 H-NMR(400.0 MHz,CDCl3):δ=7.765(0.6);7.745(1.24);7.713(1.31);7.693(0.61);7.518(0.61);7.504(1.1);7.365(2.37);7.26(110.75);7.227(1.16);6.996(0.61);4.432(1.91);4.414(2.54);4.395(1.99);2.79(8.62);2.305(16);2.065(1.18);2.047(2.14);2.028(2.13);2.01(1.26);1.018(4.29);0.999(8.94);0.98(4.15);0.008(1.31);0(45.01);-0.008(1.28) Example 3-2: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.635(1.2);7.994(0.94);7.9(0.62);7.88(1.28);7.857(0.62);7.847(1.64);7.827(0.76);4.323(2.06);4.305(3.02);4.287(2.13);3.31(32.73);3.006(16);2.669(0.58);2.587(9.22);2.523(1.72);2.518(2.56);2.51(32.26);2.505(70.05);2.5(97.77);2.496(68.17);2.491(30.37);2.327(0.54);1.918(1.19);1.9(2.12);1.882(2.12);1.864(1.21);0.908(4.27);0.89(9.45);0.871(4.02);0.008(0.59);0(20.02);-0.009(0.56) Example 3-3: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.709(2.02);8.042(0.88);8.022(1.14);7.94(1.98);7.92(2.35);7.783(2.55);7.646(1.19);4.332(3.05);4.314(4.5);4.296(3.16);3.449(22.02);3.31(102.47);3.175(0.65);3.162(0.66);2.747(16);2.674(1.3);2.669(1.84);2.665(1.3);2.551(0.5);2.54(0.62);2.535(0.75);2.523(5.28);2.518(8);2.51(105.64);2.505(228.67);2.5(317.05);2.496(221.05);2.491(98.27);2.463(0.66);2.45(0.99);2.332(1.29);2.327(1.81);2.322(1.34);1.919(1.69);1.901(3.04);1.882(3.12);1.864(1.77);0.913(6.63);0.895(14.54);0.876(6.17);0.008(1.76);0(61.61);-0.009(1.8) Example 4-1:1 H-NMR(400.0 MHz,CDCl3):δ=7.677(6.48);7.521(1.05);7.382(2.45);7.261(15.43);7.244(1.19);7.1(1.13);3.881(13.55);2.72(12.81);2.272(16);0(6.76) Example 4-2: 1 H-NMR(400.0 MHz,CDCl3):δ=7.857(0.66);7.837(1.38);7.803(1.37);7.783(0.66);7.644(2.96);7.268(0.7);7.26(67.37);4.063(1.58);3.915(0.9);3.908(14.64);3.905(3.49);3.055(1.21);2.967(0.66);2.958(16);2.62(6.52);0.008(0.82);0(30.16);-0.008(0.93) Example 4-3: 1 H-NMR(400.0 MHz,CDCl3):δ=7.945(0.87);7.854(3.09);7.807(1.93);7.668(0.94);7.603(0.77);7.519(0.67);7.26(125.38);6.996(0.66);3.971(0.5);3.898(0.6);3.874(8.69);3.195(16);2.844(11.22);0.008(1.27);0(48.95);-0.008(1.37) Example 4-4: 1 H-NMR(400.0 MHz,CDCl3):δ=7.678(5.46);7.536(1.25);7.397(2.9);7.288(1.73);7.26(81.53);3.889(16);2.754(1.62);2.735(5.25);2.726(15.87);2.716(4.96);2.698(1.55);1.589(0.52);1.223(5.31);1.204(10.84);1.186(4.93);0.008(1.22);0(28.79);-0.008(0.79) Example 4-5: 1H-NMR(400.0 MHz,CDCl3):δ=7.86(4.53);7.842(1.29);7.796(1.85);7.776(1.05);7.262(24.93);5.299(0.8);3.965(16);3.281(0.56);3.262(0.52);3.016(0.93);2.997(0.98);2.983(0.79);2.964(0.77);2.608(3.34);1.425(3.08);1.406(6.35);1.388(2.93);1.285(0.77);1.255(0.72);0(9.06) Example 4-6: 1 H-NMR(400.0 MHz,CDCl3):δ=7.957(1.24);7.899(0.89);7.879(2.38);7.862(1.52);7.841(0.91);7.818(2.72);7.68(1.54);7.665(1.82);7.518(2.1);7.355(0.51);7.259(384.1);6.995(1.99);5.298(3.43);3.966(1.1);3.869(12.06);3.296(1.61);3.277(5.09);3.258(5.26);3.24(1.71);2.85(16);1.539(2.37);1.461(1.05);1.43(5.1);1.412(10.1);1.393(4.94);1.37(1.31);1.332(7.88);1.284(10.97);1.256(4.17);0.88(0.71);0.008(5.04);0(144.57);-0.008(5.71) Example 4-25: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.0342(1.2);7.8979(1.1);7.6361(2.6);7.5898(0.6);7.4521(1.3);7.3146(0.6);3.8047(16.0);3.4855(0.5);3.3085(38.0);2.5227(1.8);2.5180(2.6);2.5093(28.2);2.5047(58.3);2.5001(80.0);2.4956(54.8);2.4910(24.8);2.4229(4.6);2.4014(0.8);2.3269(0.5);1.2364(0.9);1.1167(1.4);1.0965(1.4);0.6673(1.5);0.6553(1.4);0.0080(1.2);0.0064(0.5);-0.0002(34.3);-0.0085(1.0) Example 4-28: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.0592(1.8);7.9013(1.8);7.6478(3.8);7.6011(0.8);7.4647(1.5);7.3261(0.7);3.8054(16.0);3.3130(161.1);2.9099(1.7);2.8917(1.7);2.6696(0.9);2.5230(2.8);2.5095(54.6);2.5050(116.8);2.5005(162.6);2.4959(115.8);2.4914(53.3);2.3274(0.8);2.1905(0.8);1.9878(1.6);1.2375(0.6);1.1688(2.1);1.1506(3.6);1.1319(2.2);1.1113(2.3);1.0889(2.2);0.6566(2.3);-0.0002(27.6) Example 4-29: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.1164(3.0);8.4288(0.6);8.2920(1.2);8.1534(0.7);7.9208(2.8);7.9027(1.4);7.8295(1.3);7.8110(0.8);3.8214(16.0);3.3277(114.0);3.2046(1.0);3.1861(1.4);3.1662(1.1);2.6853(0.6);2.5254(40.1);2.5208(83.0);2.5163(114.3);2.5117(79.0);2.5072(35.9);2.3431(0.7);2.0703(0.7);2.0037(1.6);1.3551(2.0);1.3370(3.8);1.3182(2.1);1.2747(0.6);1.2522(0.8);1.2080(0.8);1.1903(1.4);1.1726(1.3);1.0397(0.8);0.7382(1.4) Example 4-30: 1 H-NMR(400.0 MHz,d6-DMSO): δ=7.9772(0.5);7.9574(1.2);7.9376(1.9);7.7136(0.8);4.5780(1.8);3.8021(16.0);3.6474(1.3);3.6289(1.4);3.6107(0.5);3.3705(11.5);3.1686(4.0);2.5234(1.9);2.5100(26.7);2.5056(54.0);2.5011(72.8);2.4966(51.3);2.4921(23.8);1.3612(1.3);1.3428(2.8);1.3247(1.5);1.2356(0.6);1.0850(1.2);1.0644(1.1);0.7614(1.2);0.7487(1.2);-0.0002(13.2) Example 4-37: 1 H-NMR(400.0 MHz,CDCl3): δ=8.1451(0.6);8.1257(1.1);8.1066(0.7);7.7963(3.7);7.6484(1.3);7.6277(1.2);7.3332(1.0);7.2602(77.4);7.1961(2.1);7.0590(1.0);3.8658(16.0);2.4727(10.8);1.5622(0.7);0.0080(0.9);-0.0002(27.2);-0.0085(0.7) Example 4-38: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.0690(1.1);7.9259(1.1);7.8977(0.9);7.7766(1.7);7.7613(2.4);7.6255(1.0);3.7408(16.0);3.3106(71.9);3.1751(1.7);3.1619(1.7);3.0900(8.1);3.0503(0.6);2.6693(0.8);2.5092(52.8);2.5049(102.7);2.5004(136.0);2.4959(96.5);2.4916(46.0);2.3268(0.8);1.2372(0.8);-0.0002(12.6) Example 4-39: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2608(0.7);7.9077(1.3);7.8869(1.1);7.8573(0.7);7.7217(1.7);7.5859(0.8);3.7525(16.0);3.7397(0.8);3.5804(1.2);3.5620(1.2);3.3099(117.1);2.6740(0.8);2.6694(1.0);2.6649(0.7);2.5228(4.2);2.5181(5.9);2.5094(59.8);2.5049(123.2);2.5003(168.7);2.4958(116.6);2.4912(53.3);2.3317(0.7);2.3271(1.0);2.3225(0.7);1.2552(2.2);1.2367(5.2);1.2184(2.2);0.0080(1.0);-0.0002(30.6);-0.0085(1.0) Example 4-40: 1 H-NMR(400.0 MHz,CDCl3): δ=8.1662(0.5);8.1466(0.8);8.1276(0.6);7.8130(3.5);7.6678(1.1);7.6472(1.0);7.3586(0.7);7.2602(83.1);7.2215(1.5);7.0843(0.8);3.9896(1.5);3.8706(16.0);3.8331(1.8);3.6488(1.5);2.9588(0.8);2.9403(2.4);2.9219(2.5);2.9034(0.8);1.2712(2.2);1.2532(4.4);1.2348(2.1);0.0079(0.9);-0.0002(29.5);-0.0085(0.8) Example 4-41: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.0781(0.8);7.9416(1.1);7.9227(0.6);7.8055(3.0);7.7846(1.1);7.6695(1.0);4.0382(0.7);4.0204(0.7);3.7485(1.7);3.7376(16.0);3.6589(1.0);3.3441(0.8);3.3097(128.8);3.2694(0.8);3.2490(0.6);2.6740(0.8);2.6694(1.0);2.6648(0.8);2.5229(4.3);2.5181(6.0);2.5094(59.3);2.5049(121.8);2.5003(166.1);2.4958(114.4);2.4912(52.1);2.3317(0.7);2.3271(1.0);2.3225(0.7);1.9876(3.0);1.2482(2.1);1.2297(4.1);1.2114(2.3);1.1923(1.2);1.1745(1.8);1.1567(0.9);0.0080(0.9);-0.0002(29.1);-0.0085(0.9) Example 4-42: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2633(0.9);7.8929(1.3);7.8750(1.0);7.8552(0.8);7.7189(2.1);7.5823(0.9);7.4594(0.5);3.7397(8.9);3.6685(1.8);3.6387(0.9);3.5752(1.8);3.5641(1.6);3.5559(1.8);3.5101(0.6);3.4853(0.8);3.3590(2.0);3.3475(1.6);3.3093(409.3);2.6740(2.2);2.6694(3.0);2.6647(2.2);2.5497(2.2);2.5228(13.1);2.5181(18.6);2.5094(180.5);2.5049(368.1);2.5003(502.5);2.4957(348.7);2.4912(159.5);2.4706(1.3);2.4655(1.4);2.3317(2.1);2.3270(2.9);2.3224(2.1);1.3196(1.5);1.2982(0.8);1.2538(3.7);1.2357(16.0);1.2178(4.1);1.2013(1.0);0.8538(1.4);0.8364(0.6);0.0080(3.4);-0.0002(158.0);-0.0085(7.0);-0.1501(0.6) Example 4-49: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.333(0.88);7.918(0.83);7.859(0.7);7.84(0.92);7.776(1.1);7.755(0.72);7.605(0.64);7.468(1.32);7.332(0.65);3.791(16);3.474(2.91);2.674(0.65);2.669(0.91);2.665(0.62);2.523(2.01);2.518(3.06);2.51(48.55);2.505(107.49);2.5(151.19);2.496(105.96);2.491(47.61);2.455(1.15);2.45(1.42);2.446(1.18);2.425(5.59);2.332(0.73);2.327(1.04);2.322(0.75);0.008(1.02);0(43.65);-0.008(1.4) Example 4-50: 1 H-NMR(400.0 MHz,d6-DMSO):δ=8.063(0.72);7.985(0.92);7.926(0.75);3.78(16);3.092(3.3);2.523(1.85);2.518(2.82);2.51(30.57);2.505(63.43);2.5(86.36);2.496(61.52);2.491(28.65);2.327(0.55) Example 4-51: 1 H-NMR(400.0 MHz,d6-DMSO):δ=8.176(1.48);8.076(1.77);8.055(1.58);7.96(2.24);7.823(1.95);3.825(16);3.595(10.57);3.402(63.21);2.694(1.86);2.548(4.42);2.543(6.94);2.534(108.49);2.53(231.87);2.525(318.71);2.521(225.86);2.516(103.46);2.352(1.86) Example 4-52: 1 H-NMR(400.0 MHz,d6-DMSO): δ=11.3456(1.1);7.9188(1.0);7.8657(0.7);7.8474(1.0);7.7935(1.2);7.7743(0.8);7.6052(0.6);7.4685(1.2);7.3325(0.6);3.7908(16.0);3.4179(1.9);3.1684(5.6);2.9482(1.6);2.9298(1.6);2.6695(0.6);2.5230(1.3);2.5183(2.0);2.5096(33.3);2.5050(73.7);2.5004(103.6);2.4958(72.8);2.4912(33.0);2.4549(0.7);2.4505(0.9);2.4459(0.6);2.3272(0.7);1.1703(1.7);1.1522(3.2);1.1342(1.9);0.0080(0.7);-0.0002(27.9);-0.0085(0.9) Example 4-53: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.2356(0.6);8.0988(1.2);8.0019(1.7);7.9620(0.9);7.9317(0.9);5.7549(2.5);5.7532(2.6);3.7799(16.0);3.5748(3.5);3.2873(1.5);3.2691(1.5);2.5052(49.2);2.5013(61.2);2.4979(46.0);1.3319(1.7);1.3137(3.2);1.2961(1.8);0.0014(8.0);-0.0002(8.3) Example 4-54: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.1904(0.7);8.1708(0.9);8.0763(1.0);8.0562(0.7);7.9493(1.4);7.7989(1.0);4.7745(1.3);3.7990(16.0);3.7420(0.7);3.7242(0.8);3.6949(1.3);3.6772(1.3);3.6598(0.6);3.6191(0.6);3.3703(14.0);2.6701(0.6);2.5233(3.0);2.5100(40.0);2.5055(79.0);2.5010(105.4);2.4965(74.2);2.4920(35.0);2.3277(0.6);1.2679(1.5);1.2498(2.8);1.2322(1.6);1.1195(0.8);1.1018(1.6);1.0840(0.8);0.0080(1.4);-0.0002(36.1);-0.0085(1.3) Example 4-61: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.317(1.92);7.912(1.73);7.8(4.35);7.617(0.87);7.48(1.79);7.344(0.9);3.815(16);3.311(53.37);3.261(0.82);2.674(0.73);2.669(0.99);2.665(0.76);2.552(0.59);2.523(2.3);2.518(3.39);2.51(52.75);2.505(116.08);2.5(162.65);2.496(114.42);2.491(53.15);2.451(3.86);2.421(9.65);2.332(0.83);2.327(1.16);2.322(0.84);0.008(1.51);0(61.65);-0.008(2.21) Example 4-63: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.473(3.87);8.107(7.38);7.969(1.31);7.946(3.93);7.832(2.21);7.696(1.12);3.855(16);3.603(14.46);3.338(145.94);2.697(1.06);2.528(176.33);2.355(1.03);2.015(1.04);1.202(0.57) Example 4-64: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.328(2.17);7.912(2.21);7.816(2.84);7.619(0.75);7.483(1.49);7.346(0.7);3.815(16);3.315(46.07);3.263(0.82);2.968(0.84);2.949(2.25);2.931(2.34);2.913(1.01);2.674(0.67);2.67(0.94);2.665(0.68);2.523(2.27);2.518(3.58);2.51(54.71);2.505(116.11);2.5(158.97);2.496(112.64);2.491(52.4);2.447(3.71);2.332(0.8);2.327(1.05);2.323(0.77);1.182(2.46);1.164(4.91);1.146(2.73);0.008(1.35);0(52.7);-0.008(2.08) Example 4-65: 1 H-NMR(400.0 MHz,d6-DMSO):δ=8.174(1.02);8.052(1.27);7.986(1.22);7.955(1.36);3.828(12.61);3.548(16);3.297(1.3);2.698(0.93);2.533(111.33);2.528(151.51);2.524(117.84);2.354(0.88);1.388(1.61);1.368(2.99) Example 4-66: 1H-NMR(400.0 MHz,d6-DMSO):δ=8.098(2.51);7.949(1.23);7.805(0.67);5.754(2.65);4.135(16);3.824(6.27);3.716(1.04);3.698(1.05);2.507(35.28);2.503(46.53);2.499(35.74);1.282(1.14);1.263(2.14);1.245(1.19);0(5.49) Example 4-73: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.258(2.68);7.908(2.46);7.808(1.75);7.789(2.35);7.684(2.11);7.665(1.62);7.61(1.19);7.473(2.51);7.336(1.22);3.852(16);3.309(29.72);2.669(0.58);2.523(1.41);2.518(2.12);2.509(31.57);2.505(68.77);2.5(96.02);2.496(68.07);2.491(30.91);2.387(14.1);2.332(0.52);2.327(0.68);2.322(0.51);0.008(1.48);0(50.83);-0.009(1.48) Example 4-74: 1 H-NMR(400.0 MHz,d6-DMSO):δ=8.201(1.16);8.066(1.67);7.951(1.79);7.849(1.28);7.828(1.05);3.865(16);3.086(7.03);2.698(0.95);2.529(162.8);2.354(0.98) Example 4-75: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.0572(2.0);8.0369(2.9);7.9281(4.6);7.9137(2.1);7.7875(2.1);7.6509(1.0);3.8625(16.0);3.8380(4.4);3.7837(15.1);3.5457(15.0);3.0584(0.7);2.6744(1.3);2.6697(1.8);2.6653(1.3);2.5516(1.8);2.5449(4.6);2.5309(9.4);2.5097(122.3);2.5052(234.2);2.5007(305.7);2.4961(214.7);2.4916(98.4);2.4519(1.3);2.3321(1.3);2.3275(1.8);2.3229(1.3);0.0079(1.3);-0.0002(26.9);-0.0084(0.9) Example 4-76: 1 H-NMR(400.0 MHz,d6-DMSO):δ=11.263(2.98);7.908(3.37);7.823(1.96);7.802(2.43);7.689(2.25);7.67(1.89);7.615(1.23);7.478(2.49);7.34(1.24);3.851(16);3.308(51.97);2.933(1.48);2.915(3.76);2.897(3.97);2.878(1.5);2.669(0.84);2.509(53.27);2.505(113.96);2.5(157.5);2.496(110.8);2.491(50.03);2.327(0.81);1.2(4.11);1.182(8.11);1.164(4.14);0.008(1.49);0(46.07);-0.008(1.32) Example 4-77: 1H-NMR(400.0 MHz,d6-DMSO):δ=11.325(4.98);8.316(0.92);8.18(1.86);8.044(2.62);8.025(2.17);7.914(3.12);7.83(2.03);7.812(1.72);3.841(16);3.314(108.52);3.274(2.19);3.259(1.75);3.235(1.04);3.214(1.46);3.198(1.43);3.18(1.13);3.164(0.82);2.674(1.48);2.67(1.94);2.665(1.38);2.523(7.61);2.509(130.64);2.505(254.8);2.5(331.08);2.496(233.82);2.492(114.74);2.332(1.64);2.327(2.06);2.072(0.76);1.393(3.77);1.375(7.41);1.356(3.97);0.008(2.62);0.001(36.17);0(52.19);-0.008(2.17) Example 4-78: 1 H-NMR(400.0 MHz,d6-DMSO):δ=8.086(1.73);8.066(2.41);7.954(2.16);7.928(3.89);7.788(1.83);7.652(0.87);3.861(13.04);3.774(16);3.698(3.82);3.679(3.57);3.661(1.52);2.67(1.78);2.523(4.5);2.518(6.77);2.51(98.48);2.505(213.47);2.501(296.57);2.496(207.91);2.492(92.34);2.328(1.65);2.072(1.37);1.306(3.22);1.288(6.95);1.27(3.01);0.008(1.64);0(58.19);-0.008(1.91) Example 5-1: 1H-NMR(400.0 MHz,CDCl3):δ=7.783(0.59);7.685(0.8);7.665(1.75);7.633(1.65);7.613(0.77);7.503(0.93);7.365(2.03);7.26(83.93);7.227(0.97);7.21(0.55);4.145(1.68);2.76(10.22);2.522(1.57);2.513(12.53);2.495(1.81);2.468(1.37);2.297(16);2.262(1.93);1.55(1.06);1.269(0.93);1.038(0.9);0.008(0.97);0(35.94);-0.008(1.14) Example 5-2: 1 H-NMR(400.0 MHz,CDCl3):δ=7.842(0.83);7.822(1.2);7.741(1.21);7.721(0.83);7.519(0.81);7.26(149.61);7.21(1.2);6.996(0.81);2.95(16);2.56(6.37);2.502(15.6);1.548(1.99);0.008(1.71);0(63.1);-0.008(1.72) Example 6-4: 1 H-NMR(400.0 MHz,CDCl3):δ=7.7(1.58);7.68(2.83);7.667(1.09);7.623(2.63);7.603(1.55);7.524(1.52);7.386(3.25);7.266(0.59);7.266(0.68);7.265(0.87);7.264(1.12);7.26(67.17);7.248(1.69);2.777(2.16);2.759(6.92);2.751(16);2.74(6.59);2.722(2.12);1.581(1.4);1.243(7.3);1.225(15.01);1.206(6.88);0.008(0.78);0(26.31);-0.008(0.67) Example 6-5: 1H-NMR(400.0 MHz,CDCl3):δ=9.616(0.89);7.825(3.54);7.805(5.32);7.738(7.15);7.718(4.84);7.519(2.95);7.295(0.71);7.287(0.59);7.283(0.66);7.281(0.62);7.28(0.82);7.279(0.94);7.278(0.98);7.277(1.06);7.276(1.11);7.276(1.23);7.275(1.28);7.274(1.54);7.273(1.58);7.272(1.75);7.272(2.04);7.271(2.41);7.27(2.79);7.269(3.23);7.269(3.51);7.268(3.91);7.267(4.83);7.266(6.04);7.265(7.71);7.264(9.93);7.26(522.59);7.256(6);7.255(4.35);7.254(3.49);7.253(2.95);7.252(2.34);7.252(1.78);7.251(1.71);7.25(1.38);7.249(1.32);7.248(1.32);7.248(1.23);7.247(1.01);7.246(0.92);7.245(1);7.244(0.79);7.244(0.78);7.243(0.69);7.242(0.73);7.241(0.67);7.24(0.59);7.24(0.71);7.239(0.64);7.236(0.59);7.232(0.52);7.228(0.62);7.21(0.65);6.996(2.77);5.298(0.53);3.265(0.62);3.247(1.93);3.229(2.25);3.214(2.55);3.195(2.39);3.177(0.8);2.982(1.09);2.963(4.08);2.948(1.27);2.944(4.25);2.93(3.43);2.925(1.54);2.91(3.31);2.892(1.06);2.506(16);1.576(67.91);1.49(1.05);1.421(13.84);1.402(28.46);1.383(12.97);1.37(1);1.33(0.75);1.285(1.54);1.256(1.71);0.146(0.57);0.008(6.02);0(206.24);-0.008(5.61);-0.149(0.6). Example 6-6: 1 H-NMR(400.0 MHz,CDCl3):δ=8.161(0.52);7.924(1.71);7.904(2.51);7.821(1.51);7.81(1.18);7.801(1.07);7.673(1.84);7.535(0.94);7.26(73.64);3.286(1.79);3.267(5.88);3.248(5.99);3.23(1.85);2.806(16);1.547(3.33);1.426(5.36);1.407(11.09);1.389(5.05);0.008(1.08);0(28.46);-0.008(0.85) Example 7-1: 1 H-NMR(400.0 MHz,CDCl3):δ=7.688(0.76);7.668(1.42);7.624(1.56);7.604(0.83);7.496(1.04);7.357(2.44);7.266(0.56);7.266(0.68);7.265(0.85);7.26(52.32);7.219(1.26);4.126(0.93);2.748(10.89);2.582(0.99);2.531(16);2.46(0.81);2.283(15.03);0.008(0.75);0(22.28);-0.008(0.61) Example 7-2: 1 H-NMR(400.0 MHz,d6-DMSO): δ=7.979(1.0);7.842(0.5);7.790(5.8);5.753(1.6);3.309(25.9);2.989(16.0);2.537(9.3);2.523(1.4);2.518(1.8);2.509(19.5);2.505(41.8);2.500(58.2);2.496(41.3);2.491(19.5);2.485(13.1);0.000(13.3) Example 7-3: 1H-NMR(400.0 MHz,CDCl3):δ=7.938(1.26);7.842(1.97);7.822(0.54);7.8(2.82);7.661(1.44);7.52(1.23);7.311(0.5);7.261(208.56);6.996(1.21);3.206(16);2.831(14.52);2.534(13.34);1.545(2.44);0.008(2.67);0(92.86);-0.008(2.76) Example 7-4: 1 H-NMR(400.0 MHz,CDCl3):δ=7.689(1.07);7.668(2.22);7.632(1.94);7.612(0.94);7.517(0.93);7.379(2.09);7.261(28.01);7.24(1.03);5.299(1.21);2.764(1.27);2.745(4.06);2.734(11.3);2.726(4.32);2.708(1.29);2.526(16);1.229(4.49);1.21(9.27);1.192(4.23);0(10.2) Example 7-11: 1 H-NMR(400.0 MHz,CDCl3):δ=7.66(1);7.64(2.9);7.62(2.1);7.599(0.76);7.513(1.11);7.374(2.53);7.261(31.84);7.236(1.28);5.299(2.55);3.217(0.86);3.199(2.88);3.18(2.94);3.162(0.9);2.532(16);2.313(15.92);1.25(1.49);1.232(2.93);1.213(1.43);0(13.53) Example 7-12: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.191(0.74);8.105(0.88);7.854(0.51);7.833(2.41);7.823(1.92);3.311(26.21);3.175(0.51);3.162(0.51);3.03(16);2.846(0.55);2.523(0.76);2.518(1.24);2.51(16.09);2.505(34.38);2.5(47.68);2.496(33.94);2.491(18.19);1.209(2.47);1.191(5.96);1.172(2.44);0(12.07) Example 7-13: 1 H-NMR(400.0 MHz,d6-DMSO):δ=12.284(1.91);7.972(2.8);7.952(5.13);7.914(6.07);7.895(4.46);7.76(5.53);7.624(2.74);3.425(40.65);3.375(0.71);3.31(156.79);3.26(1.2);3.19(4.01);3.174(4.57);3.162(2.89);3.019(0.57);2.67(1.54);2.509(103.43);2.505(199.64);2.5(263.74);2.496(199.47);2.45(2.82);2.327(1.79);1.232(7.42);1.214(16);1.196(7.18);1.097(0.77);1.022(0.74);1.006(0.65);0(45.05) Example 7-14: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.098(1.07);7.667(3.86);7.663(4.92);7.638(1.19);7.5(3.23);7.363(1.46);5.754(3.08);3.31(89.88);3.26(0.78);3.087(0.6);3.07(1.7);3.051(1.72);3.033(0.63);2.795(1.75);2.776(5.81);2.758(5.86);2.739(1.86);2.674(0.64);2.669(0.87);2.665(0.63);2.523(1.96);2.518(2.92);2.51(47.85);2.505(105.77);2.5(149.11);2.496(104.09);2.491(46.99);2.486(16.77);2.467(0.77);2.455(1.29);2.451(1.37);2.446(0.86);2.332(0.69);2.327(0.94);2.322(0.68);2.072(0.57);1.174(7.09);1.166(3.91);1.155(16);1.147(9.93);1.137(7.11);1.128(3.84);0.008(2.34);0.006(0.52);0.006(0.55);0.005(0.65);0.004(0.88);0.003(1.49);0.002(2.69);0.002(4.22);0(83.52);-0.003(4.54);-0.003(2.92);-0.004(1.79);-0.005(1.32);-0.006(1.09);-0.007(0.97);-0.008(0.99);-0.008(2.5);-0.011(0.55);-0.05(0.54) Example 7-15: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.2(1.5);8.087(0.69);7.857(1.06);7.836(4.77);7.826(4.02);7.806(0.88);3.31(124.99);3.29(0.62);3.271(1.38);3.26(1.29);3.253(1.64);3.238(2.02);3.22(1.95);3.201(0.56);3.118(0.5);3.099(1.68);3.08(1.8);3.066(1.33);3.047(1.22);2.964(0.58);2.87(0.72);2.853(0.89);2.836(0.66);2.674(0.8);2.669(1.14);2.665(0.82);2.523(2.79);2.518(4.14);2.51(63.33);2.505(140.43);2.5(198.05);2.496(137.85);2.491(63.3);2.486(24.91);2.46(0.94);2.455(1.39);2.45(1.88);2.446(1.55);2.441(0.97);2.332(0.98);2.327(1.27);2.322(0.96);1.323(7.23);1.305(16);1.286(6.94);1.203(5.31);1.185(13.1);1.166(5.3);0.008(1.44);0(59.62);-0.009(1.78) Example 7-16: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.285(1.74);7.987(1.13);7.967(2.5);7.939(3.39);7.918(1.49);7.891(1.53);7.754(3.59);7.618(1.8);3.495(1.78);3.476(6.1);3.458(6.27);3.44(1.93);3.31(113.65);3.26(0.7);3.166(1.64);3.148(1.68);2.674(0.9);2.669(1.26);2.665(0.92);2.523(3.54);2.518(5.03);2.51(67.76);2.505(148.13);2.5(208.18);2.496(146.16);2.491(71.36);2.47(0.55);2.455(1.22);2.45(1.56);2.446(1.18);2.332(0.94);2.327(1.33);2.322(0.95);1.265(6.82);1.247(16);1.228(7.02);1.22(4.53);1.202(10.39);1.184(4.33);0.008(2.23);0(85.2);-0.004(1.13);-0.005(0.79);-0.006(0.68);-0.007(0.63);-0.008(2.41) Example 7-47: 1 H-NMR(400.0 MHz,d6-DMSO): δ=12.3070(2.4);11.4223(0.7);7.7989(6.2);7.7790(14.0);7.7563(16.0);7.7361(5.9);7.5962(5.3);7.4592(11.9);7.3226(5.8);4.0859(0.7);4.0077(0.6);3.8043(0.6);3.3105(152.1);3.1746(3.3);3.1626(3.0);2.6742(2.9);2.6696(3.6);2.6648(2.8);2.5868(5.2);2.5094(218.0);2.5050(397.9);2.5004(513.0);2.4960(361.2);2.4915(177.5);2.4520(5.4);2.4305(19.4);2.4139(76.2);2.3930(3.2);2.3629(1.2);2.3479(1.8);2.3321(2.7);2.3272(3.4);2.2618(1.7);2.1052(5.1);1.9153(0.6);1.2989(0.5);1.2353(2.3);-0.0002(43.6) Example 7-48: 1 H-NMR(400.0 MHz,d6-DMSO): δ=12.3984(0.7);8.2036(0.9);8.0666(1.5);7.9723(2.9);7.9652(3.2);7.9448(0.5);7.9295(1.0);3.3267(60.2);3.0981(16.0);2.5385(2.0);2.5338(2.8);2.5251(27.8);2.5205(57.2);2.5159(78.4);2.5114(53.6);2.5068(25.0);2.4994(6.9) Example 7-49: 1 H-NMR(400.0 MHz,d6-DMSO): δ=12.4960(1.2);8.1011(1.2);8.0495(2.0);8.0291(1.2);7.9414(1.0);7.8049(2.4);7.6679(1.2);4.0541(1.1);4.0363(1.0);3.5704(16.0);3.3765(0.6);3.3257(79.3);3.3134(1.8);3.3089(0.9);3.3031(0.5);3.2759(1.2);3.0732(0.6);2.6895(0.7);2.6850(1.0);2.5892(0.6);2.5759(0.8);2.5711(0.9);2.5665(0.8);2.5501(0.7);2.5387(3.2);2.5340(4.9);2.5253(52.3);2.5208(109.5);2.5162(152.1);2.5116(105.5);2.5071(49.3);2.5002(5.5);2.4954(2.7);2.4715(1.2);2.4670(1.8);2.4623(1.6);2.4574(1.1);2.4540(0.7);2.4451(0.6);2.4404(0.5);2.4173(0.7);2.3430(0.9);2.2580(0.6);2.0036(4.6);1.2081(1.4);1.1904(2.7);1.1726(1.4) Example 7-50: 1 H-NMR(400.0 MHz,d6-DMSO): δ=7.7852(0.8);7.7749(1.0);7.4596(0.7);3.3497(16.0);2.9360(1.0);2.9176(1.0);2.5123(3.5);2.5077(7.3);2.5031(10.1);2.4986(7.0);2.4940(3.4);2.4845(1.4);1.9175(0.6);1.1652(1.2);1.1468(2.5);1.1364(0.6);1.1284(1.2) Example 7-51: 1 H-NMR(400.0 MHz,d6-DMSO): δ=7.9641(0.7);7.9515(0.8);3.3105(16.0);3.2738(0.7);3.2553(0.7);2.5229(0.6);2.5094(10.1);2.5049(21.0);2.5004(28.8);2.4958(20.0);2.4913(9.1);2.4774(2.2);1.3241(0.8);1.3055(1.6);1.2868(0.8) Example 7-52: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.1218(0.9);7.9739(9.1);7.9528(1.2);7.9095(1.7);7.8961(1.2);7.8764(1.1);7.7728(3.7);7.6365(1.8);4.0383(1.7);4.0206(1.7);4.0028(1.0);3.6786(3.5);3.6600(7.9);3.6416(7.8);3.6227(3.2);3.3074(136.1);3.2562(1.0);2.6692(6.8);2.5089(156.6);2.5046(276.6);2.5001(358.5);2.4956(270.3);2.4461(1.1);2.4045(17.7);2.3269(2.1);2.1780(0.7);2.1232(1.0);1.9875(5.0);1.9077(0.5);1.2461(8.2);1.2276(16.0);1.2090(7.3);1.1923(1.7);1.1746(2.9);1.1567(1.6);0.8735(0.8);0.8545(0.5);-0.0002(25.6) Example 7-59: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.285(11.15);7.797(7.79);7.777(16);7.741(11.02);7.722(6.04);7.607(7.23);7.588(1.37);7.543(1.25);7.47(15.69);7.333(7.54);3.806(2.57);3.309(308.67);3.259(2.39);2.674(3.82);2.669(5.18);2.665(3.73);2.556(1.87);2.522(21.21);2.509(336.55);2.505(677.17);2.5(910.54);2.496(647.97);2.491(314.67);2.451(8.82);2.409(92.72);2.39(5.64);2.332(4.77);2.327(6.16);2.323(4.7);2.072(8.25);0.146(1.44);0.008(16.38);0(391.24);-0.008(14.27);-0.05(2.19);-0.15(1.69) Example 7-60: 1 H-NMR(400.0 MHz,d6-DMSO): δ=3.3107(16.0);3.0709(3.6);2.5228(0.7);2.5095(13.7);2.5050(28.8);2.5005(39.6);2.4959(27.7);2.4915(12.6);2.4611(2.8) Example 7-62: 1H-NMR(400.0 MHz,d6-DMSO):δ=12.297(3.89);7.813(2.72);7.793(4.79);7.745(2.81);7.725(1.74);7.608(2.26);7.471(5.25);7.335(2.53);3.312(116.32);3.279(1.3);3.262(1.7);3.243(0.79);2.954(2.05);2.935(6.37);2.917(6.6);2.898(2.49);2.674(1.25);2.67(1.78);2.665(1.3);2.551(0.94);2.523(4.29);2.518(6.37);2.51(95.36);2.505(211.57);2.5(298.93);2.496(212.49);2.491(102.95);2.451(6.21);2.332(1.45);2.327(1.99);2.323(1.49);2.073(0.82);1.174(7.7);1.156(16);1.137(7.73);0.008(2.67);0.006(0.55);0.006(0.59);0.005(0.7);0(94.47);-0.005(2.23);-0.006(1.94);-0.007(1.75);-0.008(3.38);-0.051(0.56) Example 7-71: 1 H-NMR(400.6 MHz,d6-DMSO):δ=7.808(1.5);7.789(1.75);7.615(1.07);7.595(0.94);7.583(1.11);7.446(2.14);7.309(1.05);4.152(16);3.187(1.47);3.183(2.73);3.179(3.8);3.175(2.65);3.171(1.34);2.58(1.33);2.551(6.96);2.547(13.3);2.542(17.67);2.538(12.57);2.533(6.12);2.502(3.34);2.393(11.85);2.375(0.65);2.047(0.78);0(1.87) Example 7-72: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.3017(0.6);8.1636(1.3);8.0261(0.7);7.9259(1.1);7.9062(1.2);7.6232(1.2);7.6031(1.1);3.3090(37.8);3.0268(16.0);2.6739(0.7);2.6693(1.0);2.6646(0.7);2.5556(0.5);2.5507(0.6);2.5227(3.6);2.5180(5.1);2.5093(54.6);2.5048(112.2);2.5002(152.6);2.4956(105.2);2.4911(47.9);2.4561(0.6);2.4518(0.6);2.3878(10.1);2.3316(0.7);2.3270(0.9);2.3224(0.6);1.9075(1.3);0.0080(1.2);-0.0002(32.9);-0.0085(1.0) Example 7-74: 1 H-NMR(400.0 MHz,d6-DMSO):δ=12.225(3.02);7.802(3.59);7.782(4.31);7.625(2.36);7.605(4);7.468(4.83);7.331(2.29);3.308(31.48);2.922(2.06);2.904(6.48);2.885(6.79);2.867(2.46);2.67(0.72);2.523(2.24);2.51(44.57);2.505(95.06);2.5(132.34);2.496(96.1);2.491(47.54);2.327(0.76);1.193(7.72);1.174(16);1.156(7.79);0.008(1.47);0(50.69);-0.009(1.57) Example 7-75: 1 H-NMR(400.0 MHz,d6-DMSO): δ=8.3100(0.6);8.1716(1.3);8.0333(0.7);7.8209(1.7);7.8009(1.9);7.4686(2.2);7.4487(2.0);4.0881(0.7);4.0747 (0.8);3.3109(62.3);3.2707(1.2);3.2518(0.8);3.2372(1.2);3.2183(1.1);3.1743(3.5);3.1613(3.8);3.1444(1.0);3 .1262(1.1);3.1106(0.7);3.0927(0.6);2.6693(0.6);2.5498(0.7);2.5450(0.7);2.5046(66.7);2.5001(94.3);2.4957(73.7);2.3270(0.6);2.2695(16.0);1.3734(3.2);1.3549(6.7);1.3363(3.2);0.0080(0.9);-0.0002(27.5);-0.0084(1.6) Example 9-25: 1 H-NMR(400.0 MHz, CDCl3):δ=7.963(1.47);7.942(1.75);7.712(1.65);7.692(1.43);7.518(0.58);7.449(0.9);7.312(1.97);7.271(0.56 );7.271(0.56);7.268(0.79);7.259(100.61);7.174(0.95);6.995(0.57);2.423(16);0.008(1.4);0(43.08);-0.008(1.14)

[0102] B. Formulation Examples a) 10 parts by weight of the compound of formula (I) and / or its salt are mixed with 90 parts by weight of talc as an inert substance, and the mixture is ground in a hammer mill to obtain a dust product.

[0103] b) 25 parts by weight of a compound of formula (I) and / or its salt, 64 parts by weight of kaolin-containing quartz as an inert substance, 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleoyl methyl taurate as a wetting agent and dispersant are mixed, and the mixture is ground in a pen-stop disc mill to obtain a readily water-dispersible wettable powder.

[0104] c) A readily water-dispersible dispersant is obtained by mixing 20 parts by weight of a compound of formula (I) and / or its salt with 6 parts by weight of an alkylphenol polyglycol ether (Triton X 207®), 3 parts by weight of isotridecanol polyglycol ether (8EO), and 71 parts by weight of a paraffinic mineral oil (e.g., boiling range of about 255-277°C or greater), and grinding the mixture in an attrition ball mill to a fineness of less than 5 microns.

[0105] d) An emulsion is obtained from 15 parts by weight of a compound of formula (I) and / or a salt thereof, 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of ethoxylated nonylphenol as an emulsifier.

[0106] e) 75 parts by weight of a compound of formula (I) and / or a salt thereof, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin The mixture is mixed, pulverized in a pinned disc mill, and the powder is granulated in a fluidized bed by spraying water as a granulating liquid to obtain water dispersible granules.

[0107] f) 25 parts by weight of a compound of formula (I) and / or a salt thereof, 5 parts by weight of sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, 2 parts by weight of sodium oleoyl methyl taurate, 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water Water dispersible granules can also be obtained by homogenizing and pre-grinding the above in a colloid mill, then grinding the mixture in a head mill, and atomizing and drying the resulting suspension in a spray tower using a single-phase nozzle.

[0108] C. Biological Examples The abbreviations used herein mean the following: ABUTH Abutilon theophrasti ALOMY Alopecurus myosuroides AMARE Amaranthus retroflexus AVEFA Oat (Avena fatua) CYPES Cyperus serotinus MATIN Matricaria inodora PHBPU Pharbitis purpureum POLCO Polygonum convolvulus SETVI Green foxtail (Setaria viridis) STEME Common chickweed (Stellaria media) VERPE Veronica persica VIOTR Viola tricolor

[0109] 1. Pre-emergence herbicidal effect against harmful plants Seeds of monocotyledonous and dicotyledonous weed plants and crop plants are placed in sandy loam in wood fiber pots and covered with soil. A compound of the present invention formulated as a wettable powder (WP) or emulsifiable concentrate (EC) is then applied to the surface of the covered soil in the form of an aqueous suspension or emulsion with the addition of 0.2% wetting agent at a water application rate equivalent to 600-800 l / ha. After treatment, the pots are placed in a greenhouse and maintained under favorable growing conditions for the test plants. Damage to the test plants is visually assessed after a 3-week test period, compared with untreated controls (percent herbicidal activity (%): 100% activity = plants killed, 0% activity = similar to control plants). Here, many compounds according to the present invention showed at least 80% activity against many important harmful plants at application rates of 320 g / ha or less.

[0110] In addition, some substances are harmless to dicotyledonous crops such as soybean, cotton, rapeseed, sugar beet or potato.Some compounds according to the present invention show high selectivity, and are therefore suitable for controlling undesirable vegetation in agricultural crops by pre-emergence method.The data in the following tables A and B show the pre-emergence herbicidal activity of compounds according to the present invention in a typical manner, and herbicidal activity is stated in %.

[0111] [Table 11A] [Table 11B] [Table 11C]

[0112] [Table 12A] [Table 12B] [Table 12C]

[0113] 2. Post-emergence herbicidal effect against harmful plants Seeds of monocotyledonous and dicotyledonous weeds and crop plants are placed in sandy soil in wood fiber pots, covered with soil, and cultivated in a greenhouse under favorable growing conditions. Two to three weeks after sowing, the test plants are treated at the one-leaf stage. Compounds of the present invention, formulated in the form of wettable powders (WP) or emulsifiable concentrates (EC), are then sprayed onto the green parts of the plants in the form of aqueous suspensions or emulsions, with the addition of 0.2% wetting agent, at a water application rate equivalent to 600-800 l / ha. After the test plants are left in the greenhouse under optimal growing conditions for approximately three weeks, the activity of the preparations is visually assessed in comparison with untreated controls (percent herbicidal activity (%): 100% activity = plant killed, 0% activity = similar to control plants). Here, many compounds of the present invention exhibited at least 80% activity against many important harmful plants at application rates of 80 g per hectare or less. At the same time, even at high active compound dosages, when applied after emergence, the compounds of the present invention leave Gramineae crops such as barley, wheat, rye, millet / sorghum, corn or rice substantially undamaged.In addition, some substances are also harmless to dicotyledonous crops such as soybean, cotton, rapeseed, sugar beet or potato.Some of the compounds of the present invention have high selectivity and are therefore suitable for controlling undesirable vegetation in agricultural crops by post-emergence method.The data in the following Tables C and D show the pre-emergence herbicidal activity of the compounds of the present invention in a typical manner, and herbicidal activity is stated in %.

[0114] [Table 13A] [Table 13B] [Table 13C]

[0115] [Table 14A] [Table 14B] [Table 14C]

[0116] 3. Comparative Experiment For comparison, the herbicidal activity of a number of compounds according to the invention was tested by the pre-emergence and post-emergence method together with the structurally closest compounds known from the documents WO 2011 / 035874, WO 2012 / 028579 and WO 2012 / 126932. These data are listed in Tables E to M below, where in each comparative pair the first compound is a compound according to the invention and the second compound is a compound known from the prior art.

[0117] [Table 15]

[0118] [Table 16]

[0119] [Table 17]

[0120] [Table 18]

[0121] [Table 19A] [Table 19B] [Table 19C]

[0122] Table 20A Table 20B Table 20C Table 20D Table 20E

[0123] Table 21A Table 21B Table 21C Table 21D Table 21E

[0124] Table 22

[0125] Table 23

Claims

1. A benzoylamide of formula (I) or a salt thereof 【Chemical 1】 wherein the symbols and indices are defined as follows: Q is the group Q4 【Chemistry 2】 represents X is (C 1 ~C 6 )-alkyl, (C 3 ~C 6 )-cycloalkyl or halogen; R (C 1 ~C 6 )-alkyl, (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, R a represents hydrogen, R Z (C 1 ~C 6 )-alkyl; n represents 0, 1 or 2 〕 (However, the compounds 4-difluoromethyl-3-ethylsulfinyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and 4-difluoromethyl-3-ethylsulfonyl-2-methyl-N-(5-methyl-1,3,4-oxadiazol-2-yl)benzamide and their sodium salts are excluded.)

2. Q is the group Q4 【Chemistry 3】 represents X is (C 1 ~C 6 )-alkyl or (C 3 ~C 6 )-cycloalkyl, R (C 1 ~C 6 )-alkyl, (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, R a represents hydrogen, R Z But (C 1 ~C 6 )-alkyl, n represents 0, 1 or 2; 2. The benzoylamide of claim 1.

3. Q is the group Q4 【Chemistry 4】 represents X represents a halogen; R (C 1 ~C 6 )-alkyl, (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, R a represents hydrogen, R Z But (C 1 ~C 6 )-alkyl, n represents 0, 1 or 2; 2. The benzoylamide of claim 1.

4. Q is the group Q4 【Chemistry 5】 represents X represents methyl, ethyl or cyclopropyl; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; R a represents hydrogen, R Z represents methyl, n represents 0, 1 or 2; 3. The benzoylamide of claim 1 or 2.

5. Q is the group Q4 【Chemistry 6】 represents X represents fluorine, chlorine, bromine or iodine; R represents methyl, ethyl, cyclopropylmethyl, or methoxyethyl; R a represents hydrogen, R Z represents methyl, n represents 0, 1 or 2; 4. The benzoylamide of claim 1 or 3.

6. 6. A herbicidal composition comprising at least one compound according to any one of claims 1 to 5 mixed with formulation adjuvants.

7. 6. The herbicidal composition according to any one of claims 1 to 5, comprising at least one further pesticide active substance from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.

8. 10. A method for controlling unwanted vegetation, comprising applying to the locus of the plants or unwanted vegetation an effective amount of at least one compound of formula (I) as defined in any one of claims 1 to 5 or a herbicidal composition as defined in claim 6 or 7.

9. 8. Use of a compound of formula (I) as defined in any one of claims 1 to 5 or a herbicidal composition as defined in claim 6 or 7 for controlling unwanted plants.

10. 10. Use according to claim 9, characterized in that the compounds of formula (I) are used to control unwanted plants in crops of useful plants.

11. 11. The use according to claim 10, characterized in that the useful plant is a transgenic useful plant.

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