n- (1,2,5-oxadiazol-3-yl) -, n- (1,3,4oxadiazol-2-yl) -, n- (tetrazol-5-yl)

专利摘要:
n- (1,2,5-oxadiazol-3-yl) -, n- (1,3,4-oxadiazol-2-yl) -, n- (tetrazol-5-yl) - and amide compounds n- (triazol-5-yl) arylcarboxylic, herbicidal composition and use thereof, as well as method for controlling unwanted plants the invention describes n- (1,2,5-oxadiazol-3-yl) -, n- ( 1,3,4-oxadiazol-2-yl) -, n- (tetrazol-5-yl) - or n- (triazol-5-yl) arylcarboxamides of formula (i) as herbicides. In this formula (i), r, v, x, y and z represent radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen. q represents a tetrazolyl, triazolyl or oxadiazolyl radical. w represents cy or n.
公开号:BR112014013872B1
申请号:R112014013872-9
申请日:2012-12-10
公开日:2019-11-19
发明作者:Köhn Armin；Hugh Rosinger Christopher；Gatzweiler Elmar；Dietrich Hansjörg；Ahrens Harmut；Häuser-Hahn Isolde；Braun Ralf；Dörner-Rieping Simon；Lehr Stefan
申请人:Bayer Ip Gmbh；
IPC主号:

专利说明:

N- (1,2,5-OXADIAZOL-3-IL) -, N- (1,3,4OXADIAZOL-2-IL) -, N- (TETRAZOL-5-IL) - AND N- (TRIAZOL-5-IL) -ARYL CARBOXYL, HERBICIDE COMPOSITION AND USE OF THE SAME, AS WELL AS A METHOD TO CONTROL UNWANTED PLANTS
description
The invention concerns the technical field of herbicides, in particular, herbicides for the selective control of broadleaf weeds and lawn grasses in useful plant cultures.
WO 2003/010143 A1 and WO 2003/010153 A1 describe N- (tetrazol-5-yl) - and N- (triazol-5-yl) -benzamides and their pharmacological activity. EP 0 049 071 A1 describes Narilbenzamides which have pharmacological activity. In the article by J. Chem. Res. (S) 1991, 11, 304 the compounds 2-methoxy-N-methyl-N- (1Htetrazol-5-yl) -benzamide, 2-hydroxy-N-methyl-N- (1 H- tetrazol-5-yl) -benzamide, 2methoxy-N-methyl-N- (1-methyl-1H-tetrazol-5-yl) -benzamide and 2-methoxy-N- (2-methyl-2Htetrazol-5-yl) -benzamide, which have pharmacological activity.
WO 00/31066 A1 describes N-pyrazolylphenoxynicotinamides or -thionicotinamides which have herbicidal activity. JP 1989009978 (A) describes N-isoxazolylbenzamides which have herbicidal activity. N- (1,2,5-oxadiazol-3-yl) -benzamides, as herbicides, are known from WO 2011/035874 A1. In European patent application EP101748937, which has a earlier priority date but which was not published before the priority date of the present patent application, N- (tetrazol-5yl) - and N- (triazol-5-yl) -benzamides and -nicotinamides particular, as herbicides. However, herbicidal activity and / or plant compatibility of the compounds specified in these publications are not always adequate. The J. Het. Chem. 1972, 9, 107-109 refers to the compound N-methyl-N- (5-phenyl-1,3,4oxadiazol-2-yl) -benzamide. The herbicidal activity of this compound is not described. The compound 3-bromo-4-methoxy-N-methyl-N- (5-phenyl-1,3,4-oxadiazol-2-yl) benzamide is known under CAS number 931735-86-3. The herbicidal activity of this compound is not described.
It is an object of the present invention to provide herbicidally active compounds which have improved properties over those of the compounds described in the prior art.
Petition 870180133768, of 9/24/2018, p. 8/165
2/144
It has now been concluded that benzoylamides substituted with particular radicals on the nitrogen atom are particularly suitable as herbicides.
Thus, the present invention provides N- (1,2,5-oxadiazol-3-yl) -, N- (1,3,4oxadiazol-2-yl) -, N- (tetrazol-5-yl) - and N - (triazol-5-yl) -arylcarboxamides of formula (I), or their salts,
V (I), where each of the symbols and indices has the meaning defined below:
R represents alkyl (C1-Ce), haloalkyl (C1-Ce), alkenyl (C2-Ce), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C3-C6), cycloalkyl (C3- C6), halocycloalkyl (C3-C6), cycloalkyl (C3-C6) -alkyl (C1-C6), halocycloalkyl (C3-C6) alkyl (C1-C6), alkyl (C1-C6) -S (O) nR ² , (C1-Ce) alkyl -OR ¹ , (C1-C6) alkyl -OCOR ¹ , (C1-C6) alkyl -OSO2R ² , (C1-Ce) alkyl -COOR ¹ , (C1-Ce) alkyl -C ( O) R ¹ , (C1-Ce) alkyl CN, (C1-C6) alkyl -SO2OR1, (C1-Ce) alkyl -CON (R ¹ ) 2, (C1-Ce) alkyl -SO2N (R ¹ ) 2, (C1-C6) alkyl -NR ¹ COR ¹ , (C1-C6) alkyl -NR ¹ SO2R ² , OR ¹ , COOR ¹ , CON (R ¹ ) 2, N (R ¹ ) 2, NR ¹ COOR ¹ , NR ¹ CON (R ¹ ) 2 or benzyl, in each case substituted with radicals of the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, the symbol W represents N or CY, each of the symbols X and Z represents, independently, hydrogen, nitro, halogen, cyano, formyl, thiocyanate, alkyl (C1-Ce), haloalkyl (C1-C6), alkenyl (C2-Ce), haloalkenyl (C2-Ce), alkynyl (C2-C6 ) , haloalkynyl (C3-C6), cycloalkyl (C3-C6), halocycloalkyl (C3-C6), cycloalkyl (C3-C6) alkyl (C1-C6), halocycloalkyl (C3-C6) -alkyl (C1-C6), COR ¹ , OR ¹ , OCOR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R1) 2, NR1SO2R ² , NR1COR ¹ , (C1-Ce) alkyl -S (O) nR ² , (C1) alkyl -Ce) -OR ¹ , (C1-Ce) alkyl -OCOR ¹ , (C1-Ce) alkyl -OSO2R ² , (C1-Ce) alkyl COOR ¹ , (C1-Ce) alkyl -SO2OR ¹ , (C1-) alkyl Ce) -CON (R ¹ ) 2, (C1-Ce) alkyl -SO2N (R ¹ ) 2, (C1-C6) alkyl -NR ¹ COR ¹ , (C1-C6) alkyl -NR ¹ SO2R ² , NR1R2, P (O) (OR ⁵ ) 2 or heteroaryl, heterocyclyl or phenyl, each substituted with radicals from the group consisting of methyl, ethyl, methoxy, nitro, trifluoromethyl and halogen, the symbol Y represents hydrogen, nitro, halogen, cyano , thiocyanate,
Petition 870180133768, of 9/24/2018, p. 9/165
3/144 alkyl (C1-Cs), haloalkyl (C1-Cs), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2Cs), haloalkynyl (C2-C6), cycloalkyl (C3-C6) ), cycloalkenyl (C3-C6), halocycloalkyl (C3-C6), cycloalkyl (C3-C6) -alkyl (C1-Cs), halo-cycloalkyl (C3-Cs) alkyl (C1-Cs), COR ¹ , COOR ¹ , OCOOR ¹ , NR1COOR ¹ , C (O) N (R ¹ ) 2, NR ¹ C (O) N (R ¹ ) 2, OC (O) N (R ¹ ) 2, C (O) N (R ¹ ) OR ¹ , NR1SO2R ² , NR1COR ¹ , OR ¹ , OSO2R ² , S (O) nR ² , SO2OR ¹ , SO2N (R1) 2, (C1-Cs) alkyl -S (O) nR ² , (C1-) alkyl Cs) -OR1, (C1-Cs) OCOR ^1, (C1-Cs) -OSO 2 R ^2, (C1-Cs) -CO2R1, (C1-Cs) -CN, alkyl (C1C6) -SO 2 OR ^1, (C1-C6) alkyl -CON (R1) 2, (C1-Cs) alkyl -SO2N (R ¹ ) 2, (C1-Cs) alkyl NR1COR ¹ , (C1-Cs) alkyl -NR ¹ SO2R ² , N ( R ¹ ) 2, P (O) (OR ⁵ ) 2, CH2P (O) (OR ⁵ ) 2, CH = NOR ¹ , (C1-Cs) alkyl -CH = NOR1, (C1-Cs) alkyl -ON = C (R1) 2, alkyl (C1-Cs) -phenyl, alkyl (C1-Cs) -heteroaryl, alkyl (C1-Cs) -heterocyclyl, phenyl, heteroaryl or heterocyclyl, where each of the last 6 radicals is replaced with radicals of the constituted set o by halogen, nitro, cyano, (C1-Cs) alkyl, haloalkyl (C1Cs), cycloalkyl (C3-Cs), S (O) n-alkyl (C1-Cs), alkoxy (C1-Cs), halo-alkoxy (C1-Cs), alkoxy (C1-Cs) -alkyl (C1-C4) and cyanomethyl, and where the heterocyclyl supports n oxo groups, or the symbols Y and Z, together with the two atoms to which they are attached form an unsaturated, partially saturated or saturated ring with 5, 6 or 7 members, which, in addition to carbon atoms, has, in each case, nitrogen atoms, n oxygen atoms, n sulfur atoms and S (O), S (O) 2, C = NR ¹⁷ , C (OR ¹⁷ ) 2, C [-O- (CH2) 2-O-] or C (O) elements, as ring members, where the carbon atoms are replaced with radicals from the group consisting of halogen, cyano, (C1-Cs) alkyl, alkenyl (C2-C10), alkynyl (C2-C10), haloalkyl (C1-Cs), alkoxy (C1-Cs) ), phenoxy, halo-alkoxy (C1-Cs), cycloalkyl (C3-Cs), alkoxyalkyl (C2-Cs) and phenyl, in which the nitrogen atoms are replaced with n radicals from the set consisting of r (C1-Cs) alkyl and phenyl, and in which the aforementioned phenyl radicals are replaced with s from the group consisting of cyano, nitro, halogen, alkyl (C1-Cs), haloalkyl (C1-C6) and alkoxy (C1-) C6), the symbol V represents hydrogen, nitro, halogen, cyano, (C1-C4) alkyl, halo (C1-C4) alkyl, OR ¹ , S (O) nR ² , the symbol R ¹ represents hydrogen, (C1-) alkyl Cs), haloalkyl (C1-Cs), alkenyl (C2-Cs), haloalkenyl (C2-Cs), alkynyl (C2-Cs), haloalkynyl (C2-Cs), cycloalkyl (C3-Cs), cycloalkenyl (C3-Cs) ), halocycloalkyl (C3-Cs), alkyl (C1-Cs) -OPetition 870180133768, of 9/24/2018, p. 10/165
4/144 (C1-Cs) alkyl, (C3-C6) cycloalkyl (C1-Cs) alkyl, phenyl, phenyl (C1-C6) alkyl, heteroaryl, (C1-C6) alkyl, heteroaryl, heterocyclyl, alkyl ( C1-C6) -heterocyclyl, (C1-C6) alkyl -O-heteroaryl, (C1-C6) alkyl -O-heterocyclyl, (C1-C6) alkyl -NR ³ heteroaryl, (C1-C6) alkyl -NR ³ - heterocyclyl, in which the last 21 radicals are replaced with radicals from the group consisting of cyano, halogen, nitro, thiocyanate, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ , OCOR ³ , SCOR ⁴ , NR ³ COR ³ , NR3SO2R ⁴ 'CO2R ³ , COSR ⁴ , CON (R ³ ) 2 and (C1-C4) alkoxy (C2-C6) -carbonyl, and where the heterocyclyl supports n oxo groups, R ² represents alkyl (C1-Ce), haloalkyl (C1-Ce), alkenyl (C2-Ce), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), (C3-C6) cycloalkyl, (C3-C6) cycloalkenyl, (C3-C6) halocycloalkyl, (C1-C6) alkyl -O (C1-C6) alkyl, (C3-C6) cycloalkyl (C1-C6) alkyl , phenyl, phenyl-(C1-C6) alkyl, heteroaryl, (C1C6) alkyl-heteroaryl, heterocyclyl, alkyl 1 (C1-C6) -heterocyclyl, (C1-C6) alkyl -O-heteroaryl, (C1-C6) alkyl -O-heterocyclyl, (C1-C6) alkyl -NR ³ -heteroaryl, (C1-Ce) alkyl - NR ³ heterocyclyl, in which the last 21 radicals are replaced with radicals from the group consisting of cyan, halogen, nitro, thiocyanate, OR ³ , S (O) nR ⁴ , N (R ³ ) 2, NR ³ OR ³ , COR ³ , OCOR ³ , SCOR ⁴ , NR ³ COR ³ , NR ³ SO2R ⁴ , CO2R ³ , COSR ⁴ , CON (R ³ ) 2 and (C1-C4) alkoxy (C2-C6) -carbonyl, and in which the heterocyclyl supports n oxo groups, the symbol R ³ represents hydrogen, (C1-Ce) alkyl, alkenyl (C2-Ce), alkynyl (C2-C6), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (C1-C6), R ⁴ represents alkyl (C1-Ce), alkenyl (C2-Ce) or alkynyl (C2-C6), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (C1- C6), the symbol R ⁵ represents (C1-C4) alkyl, the symbol n represents 0, 1 or 2, the symbol s represents 0, 1, 2 or 3, the symbol Q represents a radical Q1, Q2, Q3 or Q4 , (Q1) (Q2) (Q3) (Q4)
R ⁶ represents alkyl (C1-Ce), haloalkyl (C1-Ce), alkenyl (C2-Ce), haloalkenyl (C2-C6), alkynyl (C2-C6), halo-alkynyl (C2-C6), in that each of these 6 radicals mentioned above is replaced with s
Petition 870180133768, of 9/24/2018, p. 11/165
5/144 radicals of the group consisting of nitro, cyano, SiR ¹² 3, PO (OR ¹² ) 3, S (O) nalkyl (Ci-Ce), alkoxy (C1-Ce), halo-alkoxy (C1-C6), N (R ¹⁰ ) 2, COR ¹⁰ , COOR ¹⁰ , OCOR ¹⁰ , OCO2R ¹⁰ , NR ¹⁰ COR ¹⁰ , NR ¹⁰ SO2R ¹¹ , (C3-C6) cycloalkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl and D-benzyl, and where the last 7 radicals are replaced with radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, and where the heterocyclyl supports n oxo groups, or the symbol R ⁶ represents (C3-C7) cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is substituted by radicals of the group consisting of halogen, nitro, cyano, (C1-C6) alkyl, (C1-C6) haloalkyl (C3-C6) cycloalkyl ), S (O) n-C1-C6 alkyl, (C1-C6) alkoxy, (C1-C6) haloalkoxy and (C1-C6) alkoxy (C1C4) alkyl, R ⁷ represents (C1-) alkyl C6), haloalkyl (C1-C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), in q Each of these 6 radicals mentioned above is replaced with radicals from the group consisting of nitro, cyano, SiR ¹² 3, PO (OR ¹² ) 3, S (O) nalkyl (C1-C6), alkoxy (C1-C6), halo alkoxy (C1-C6) alkyl, N (R ¹⁰⁾ 2, COR ^10, COOR ^10, OCOR ^10, OCO2R ^10, NR ¹⁰ COR ^10, NR ¹⁰ SO 2 R ^11, cycloalkyl (C3-C6) alkyl, heteroaryl, heterocyclyl, phenyl, D-heteroaryl, D-heterocyclyl, D-phenyl and D-benzyl, and where the last 7 radicals are replaced with radicals from the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen, and where the heterocyclyl supports n groups oxo, or the symbol R ⁷ represents (C3-C7) cycloalkyl, heteroaryl, heterocyclyl or phenyl, each of which is substituted by radicals of the group consisting of halogen, nitro, cyano, (C1-C6) alkyl, (C1-) haloalkyl C6), cycloalkyl (C3-C6), S (O) n-alkyl (C1-C6), alkoxy (C1-C6), haloalkoxy (C1-C6) and alkoxy (C1-C6) -alkyl (C1C4), o R ⁸ represents hydrogen, (C1-C6) alkyl, (C3-C7) cycloalkyl, halo alkyl (C1-C6), alkoxy (C1-C6), haloalkoxy (C1-C6), alkenyl (C2-C6), alkenyloxy (C2C6), haloalkenyl (C2-C6), alkynyl (C2-C6), alkynyloxy (C2 -C6), (C2-C6) haloalkynyl, cyano, nitro, methylsulfenyl, methylsulfinyl, methylsulfonyl, (C1-C6) alkyl-carbonylamino, (C1-C6) alkoxycarbonyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonyl, methoxycarbonyl, methoxycarbonyl, methoxycarbonyl, methoxycarbonyl , methylcarbonyl, piperidinylcarbonyl, trifluoromethylcarbonyl, halogen, amino, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, methoxymethyl or heteroaryl,
Petition 870180133768, of 9/24/2018, p. 12/165
6/144 heterocyclyl or phenyl, each substituted with radicals of the group consisting of methyl, ethyl, methoxy, trifluoromethyl and halogen;
R ⁹ represents hydrogen, (C1-C6) alkyl, R ¹³ O-(C1-C6) alkyl, CH2R ¹⁴ , (C3-C ) cycloalkyl, halo (C1-C6), alkenyl (C2-C6), haloalkenyl (C2-C6), alkynyl (C2-C6), haloalkynyl (C2-C6), OR ¹³ , NHR ¹³ , methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methylcarbonyl, trifluoromethylcarbonyl, methylethylamyl, methylethylamyl, methylethylamyl, methylethylamyl, methylmethylamino, , heterocyclyl, benzyl or phenyl, each substituted with radicals of the group consisting of halogen, nitro, cyano, (C1-C6) alkyl, (C1-C6) haloalkyl, (C3-C6) cycloalkyl, S (O) n- (C1-C6) alkyl, (C1-C6) alkoxy, (C1-C6) haloalkoxy and (C1-C6) alkoxy (C1-C4) alkyl, R ¹⁰ represents hydrogen, (C1-C6) alkyl, alkenyl (C2-C6), alkynyl (C2-C6), cycloalkyl (C3-C6) or cycloalkyl (C3-C6) -alkyl (C1-C6) or phenyl, R ¹¹ represents alkyl (C1-C6), alkenyl ( C2-C6), alkynyl (C2-C6) or phenyl, the symbol R ¹² represents alkyl (C1-C6), the symbol R ^{1 3} represents hydrogen, (C1-C6) alkyl, (C1-C6) haloalkyl, (C2-C6) alkenyl, (C2-C6) haloalkenyl, (C2-C6) alkynyl, (C2-C6) haloalkyl (C3-) cycloalkyl C6), cycloalkenyl (C3-C6), halocycloalkyl (C3-C6), alkyl (C1-C6) -Oalkyl (C1-C6), cycloalkyl (C3-C6) -alkyl (C1-C6), phenyl, phenyl-alkyl (C1-C6), heteroaryl, (C1-C6) alkyl-heteroaryl, heterocyclyl, (C1-C6) alkyl-heterocyclyl, (C1-C6) alkyl -O-heteroaryl, (C1-C6) alkyl -O-heterocyclyl, (C1-C6) alkyl -NR ¹⁵ heteroaryl or (C1-C6) -NR ¹⁵ -heterocyclyl, where the last 21 radicals are replaced with radicals from the group consisting of cyano, halogen, nitro, thiocyanate, OR ¹⁵ , S (O) nR ¹⁶ , N (R ¹⁵ ) 2, NR ¹⁵ OR ¹⁵ , COR ¹⁵ , OCOR ¹⁵ , SCOR ¹⁶ , NR ¹⁵ COR ¹⁵ , NR ¹⁵ SO2R ¹⁶ , CO2R ¹⁵ , COSR ¹⁶ , CON (R ¹⁵ ) 2 e (C1-C4) alkoxy (C2C6) -alkoxy (C2C6) -carbonyl, and where the heterocyclyl supports n oxo groups, R ¹⁴ represents acetoxy, acetamido, N-methylacetamido, benzoyloxy, benzamido, N-methylbenzamido, methoxycarbonyl, ethoxy icarbonyl, benzoyl, methylcarbonyl, piperidinylcarbonyl, morpholinylcarbonyl, trifluoromethylcarbonyl, aminocarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, alkoxy (C3-C6), cycloalkyl (C3-C6) or heteroaryl, substituted by a radical, each substituted by a heterocyclyl or phenyl ethyl, methoxy, trifluoromethyl and halogen;
R ¹⁵ represents hydrogen, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C3-C6) cycloalkyl or (C3-C6) -cyclo (C1-C6) alkyl, R ¹⁶ represents (C1-C6) alkyl, (C2-C6) alkenyl or (C2-C6) alkynyl,
Petition 870180133768, of 9/24/2018, p. 13/165
7/144 the symbol R ¹⁷ represents alkyl (C1-Cs), haloalkyl (C1-Cs), alkoxy (C1-C6) and haloalkoxy (C1-C6), the symbol s represents 0, 1, 2 or 3, the symbol n represents 0, 1 or 2, the symbol D represents O, S or NR ¹¹ , excluding compounds 2-methoxy-N-methyl-N- (1H-tetrazol-5-yl) -benzamide, 2hydroxy-N- methyl-N- (1 H-tetrazol-5-yl) -benzamide, 2-methoxy-N-methyl-N- (1-methyl-1 Htetrazol-5-yl) -benzamide, 2-methoxy-N- (2 -methyl-2H-tetrazol-5-yl) -benzamide, N-methylN- (5-phenyl-1,3,4-oxadiazol-2-yl) -benzamide and 3-bromo-4-methoxy-N-methyl- N- (5-phenyl1,3,4-oxadiazol-2-yl) -benzamide.
Particularly interesting are the N- (1,3,4-oxadiazol-2-yl) -, N (tetrazol-5-yl) - and N- (triazol-5-yl) -arylcarboxamides of formula (I) , or its salts, where the symbol Q represents a radical Q1, Q2 or Q4,
^X N
R ⁶
N _x
N — N (Q4)
R ⁷ (Q1) (Q2) and all other radicals and indices have the respective meanings defined above.
More particularly interesting are the N- (1,3,4-oxadiazol-2yl) - and N- (tetrazol-5-yl) -arylcarboxamides of formula (I), or their salts, in which the symbol Q represents a Q1 or Q4 radical,
^X N
R ⁶
N — N (Q1) (Q4) and all other radicals and indices have the respective meanings defined above.
Preferred are the N- (tetrazol-5-yl) -arylcarboxamides of formula (I), or their salts, wherein Q represents the radical Q1,
Petition 870180133768, of 9/24/2018, p. 14/165
8/144
N — N ^X N (Q1) and all other radicals and indices have the respective meanings defined above.
In formula (I) and in all of the following structural formulas, alkyl radicals having more than two carbon atoms can be straight or branched. Alkyl radicals include, for example, methyl, ethyl, nou iso-propyl, n-, iso-, tert- or 2-butyl, pentyls, hexyls, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, as alkenyl, for example, allyl, 1-methylprop-2-ene-1-yl, 2-methylprop-2-ene-1-yl, but-2-ene-1-yl, but3-ene-1-yl, 1-methylbut-3-ene-1-yl and 1-methylbut-2-ene-1-yl. Alkynyl refers, for example, to propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. The multiple bond can be in any position of the unsaturated radical. Cycloalkyl refers to a saturated carbocyclic ring system having three to six carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl means a monocyclic alkenyl group that has three to six carbon members in the ring, for example, cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, where the double bond can be in any position.
Halogen refers to fluorine, chlorine, bromine or iodine.
Heterocyclyl refers to a saturated, semi-saturated or totally unsaturated cyclic radical containing 3 to 6 ring atoms, 1 to 4 of which are selected from the group consisting of oxygen, nitrogen and sulfur, and which can be further melted with a benzo ring. For example, heterocyclyl refers to piperidinyl, pyrrolidinyl, tetrahydrofuranyl, dihydrofuranyl and oxetanyl.
Heteroaryl refers to a cyclic aromatic radical containing 3 to 6 ring atoms, 1 to 4 of which are selected from the group consisting of oxygen, nitrogen and sulfur, and which can be further fused with a benzo ring. For example, heteroaryl refers to benzimidazol-2-yl, furanyl, imidazolyl, isoxazolyl, isothiazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridinyl, benzisoxazolyl, thiazolyl, pyrrolyl, pyrazolyl, 1,2-thioenyl 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-triazolyl, 1,2,3
Petition 870180133768, of 9/24/2018, p. 15/165
9/144 triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, 1,2,4-triazolyl, 1,2,4-thiadiazolyl, 1,3,4 thiadiazolyl, 1,2,3-thiadiazolyl , 1,2,5-thiadiazolyl, 2H-1,2,3,4-tetrazolyl, 1H-1,2,3,4tetrazolyl, 1,2,3,4-oxatriazolyl, 1,2,3,5-oxatriazolyl , 1,2,3,4-thiatriazolyl and 1,2,3,5tiatriazolyl.
When a group is polysubstituted with radicals, this means that that group is replaced with one or more radicals, the same or different, selected from those mentioned. Similarly, this also applies to the construction of ring systems from several atoms of elements. In this case, it is intended that compounds known to those skilled in the art as chemically unstable under standard conditions are excluded from the scope of the claims.
Depending on the nature and attachment of the substituents, the compounds of formula (I) may be present as stereoisomers. For example, when one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Likewise, stereoisomers can also occur when the symbol n represents 1 (sulfoxides). Stereoisomers can be obtained from mixtures obtained in the preparation by conventional separation methods, for example, by chromatographic separation processes. It is also possible to selectively prepare stereoisomers using stereoselective reactions using optically active starting materials and / or auxiliaries. The invention also concerns all stereoisomers, and mixtures thereof, which are covered by formula (I), but are not specifically defined. Due to the oxime-ether structure, the compounds according to the invention can also be present in the form of geometric isomers (E / Z isomers). the invention also relates to all E / Z isomers, and mixtures thereof, which are covered by formula (I), but are not specifically defined.
The compounds of formula (I) can form salts. Salts can be formed by the action of a base on those compounds of formula (I) which have an acidic hydrogen atom, for example, if the radical R ¹ contains a COOH group or a sulfonamide group -NHSO2-. Suitable bases include, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, as well as ammonium hydroxides, carbonates and hydrogen carbonates, alkali metals or alkaline earth metals, in particular sodium and potassium hydroxide , sodium and potassium carbonate and sodium and potassium hydrogen carbonate. These salts are compounds in which hydrogen
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10/144 acidic is replaced by an agriculturally suitable cation, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary ammonium salts, for example, with cations of the general formula [NRR'RR '] ⁺ , where each of the symbols R to R' represents, independently of each other, a organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. Alkylsulfonium and alkylsulfoxonium salts, such as trialkyl (C1 -C4) -sulfonium and trialkyl (C1 -C4) -sulfoxonium salts are also useful.
The compounds of formula (I) can form salts by adding a suitable inorganic or organic acid, for example, mineral acids, for example, HCI, HBr, H2SO4, H3PO4 or HNO3, or organic acids, for example, carboxylic acids , such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid, or sulfonic acids, for example, ptoluenesulfonic acid, in a basic group, for example, amino, alkylamino, dialkylamino, piperidine, morpholino or pyridine. Such salts thus contain the conjugated base of the acid as an anion.
The compounds of the invention can be prepared, for example, according to the method shown in scheme 1, by reacting an N- (1,2,5oxadiazol-3-yl) -, N- (1,3,4 -oxadiazol-2-yl) -, N- (tetrazol-5-yl) - or N- (triazol-5-yl) -arylcarboxamide (II) with a compound of formula (III), where the symbol L represents a removable group, for example, chlorine, bromine, iodine, mesyloxy, tosyloxy, trifluoromethylsulfonyloxy, etc .:
Layout 1
(II)
(III)
Base
The N- (1,2,5-oxadiazol-3-yl) -arylcarboxamides of formula (II) are known in principle and can be prepared by the methods described in WO 2011/035874 A1.
The compounds of formula (III), wherein L represents a removable group, for example, chlorine, bromine, iodine, methylsulfonyloxy, tosyloxy or
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11/144 trifluoromethylsulfonyloxy, are commercially available or can be prepared by known methods described in the literature.
The compounds of the invention can also be prepared according to the method shown in scheme 2, by reacting an amine of formula (IV) with an acid chloride (V), as described, for example, in J. Het. Chem. (1972), 9 (1), 107-109):
The compounds of the invention can also be prepared according to the method shown in scheme 3, by reacting an amine of formula (IV) with an acid of formula (VI):
(iv)
Activation
For activation, it is possible to use dehydrating reagents that are typically used for amidation reactions, for example, 1, Γ-carbonyldiimidazole (CDI), dicyclohexylcarbodiimide (DCC), 2,4,6-trioxide 2,4, 6-tripropyl-
1,3,5,2,4,6-trioxatrifosfinane (T3P), etc.
Benzoyl chlorides of formula (V), or their original benzoic acids of formula (VI) are known in principle and can be prepared, for example, by the methods described in US 6 376 429 B1, EP 1 585 742 A1 and EP 1 202 978 A1.
The amines of formula (IV) are either commercially available or are known from the literature or can be prepared, for example,
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12/144 example, by the methods described in scheme 4, by means of catalyzed alkylation with base or by means of reductive alkylation, or according to the method described in scheme 5, by means of nucleophilic substitution of a removable group L by amines R -NH2.
Layout 4
(IV)
Layout 5
Ck
L (VII)
I R (IV)
The amines of formula (IV) can also be prepared by cyclization reactions, as described, for example, in J. Org. Chem. 73 (10), 3738-3744 (2008), where the symbol Q = Q1, or in Buletinul Institutului Politehnic din lasi (1974), 20 (1-2), 95-99, or in J. Org. Chem. 67 (21), 7361-7364 (2002), where the symbol Q = Q4.
The sets of compounds of formula (I) and / or their salts that can be synthesized by the aforementioned reactions can also be prepared in parallel, in which case this can be achieved in a manual, partially automated or fully automated manner. For example, it is possible to automate the course of the reaction, the processing or the purification of the products and / or intermediates. Overall, this intends to designate a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999, on pages 1 to 34.
For the parallelized course of reaction and processing, it is possible to use several commercially available instruments, for example, Calypso reaction blocks from Barnstead International, Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Walden, Essex, CB11 3AZ, England, or MultiPROBE automated workstations from PerkinElmer, Waltham,
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Massachusetts 02451, USA. For the parallel purification of the compounds of formula (I) and their salts or intermediates that occur in the course of preparation, as available devices are chromatography devices, for example, from ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
The referred devices provide a modular procedure, in which the individual processing steps are automated, although manual operations have to be carried out between the processing steps. This can be overcome by using partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Automation systems of this type can be purchased, for example, from Caliper, Hopkinton, MA 01748, USA.
The implementation of individual or multiple synthesis steps can be supported by the use of cleaning reagents / resins supported on polymers. In the specialized literature, sets of experimental protocols are described, for example, in ChemFiles, Vol. 4, No. 1, PolymerSupported Scavengers and Reagents for Solution-Phase Synthesis (SigmaAldrich).
In addition to the methods described herein, the compounds of formula (I) and their salts can be prepared, in whole or in part, by solid-phase support methods. For this purpose, the individual intermediates or all intermediates in the synthesis or in a synthesis adapted for the corresponding procedure are bonded to a synthetic resin. Synthesis methods supported by solid phase are adequately described in the technical literature, for example, by Barry A. Bunin in “The Combinatorial Index”, Academic Press, 1998 and in Combinatorial Chemistry - Synthesis, Analysis, Screening (editor: Günther Jung), Wiley, 1999. The use of synthesis methods with solid phase support allows different protocols to be carried out, which are known from the literature and which, in turn, can be carried out manually or automated. The reactions can be carried out, for example, using IRORI technology in micro-reactors from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Solid-phase and liquid-phase procedures of individual or multiple synthesis steps can be supported through the use of microwave technology. In the technical literature, experimental protocol sets are described, for example, in Microwaves in Organic and Medicinal Chemistry (editor C. O. Kappe and A. Stadler), Wiley, 2005.
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The preparation by the processes described herein provides compounds of formula (I) and their salts in the form of sets of substances, which are called libraries. The present invention also provides libraries that comprise at least two compounds of formula (I) and their salts.
The compounds of formula (I) according to the invention (and / or their salts), hereinafter also collectively referred to as "compounds according to the invention", have an excellent herbicidal efficacy against a wide spectrum of monocot weed plants and economically important annual dicots. The active ingredients also have good control over perennial weed plants that are difficult to control and that produce shoots from rhizomes, rooted chips and other perennial organs.
Accordingly, the present invention also provides a method for controlling unwanted plants or for regulating plant growth, preferably in plant cultures, in which one or more compounds according to the invention are applied to plants (for example , weed plants, such as monocots or dicots or unwanted crop plants), to seeds (for example, grains, seeds or vegetative propagules such as tubers or bud parts with buds) or to the area in which the plants grow (for example, the area under cultivation). The compounds according to the invention can be applied, for example, before cultivation (if appropriate also by incorporation into the soil), before emergence or after emergence. Specific examples of some representatives of the flora of monocotyledonous and dicotyledonous herbs that can be controlled by the compounds according to the invention include the following, although such enumeration is not intended to be a restriction to particular species:
monocot weed plants of the genus: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Erochl Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum;
dicotyledonous herbs of the genus: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euopsia , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia,
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Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Solanum, Sonan Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
When the compounds according to the invention are applied to the soil surface before germination, then the emergence of seed shoots is completely prevented or the seeds grow until they reach the cotyledonous stage, then stopping the growth and eventually, after three within four weeks, they die completely.
If the active ingredients are applied post-emergence to the green parts of the plants, then the growth is stopped after treatment and the harmful plants remain in the growth stage of the moment of application, or they die completely after some time, in such a way that the competition for parts of weeds, which is detrimental to crop plants, is thus eliminated very early and in a prolonged way.
Although the compounds according to the invention have an excellent herbicidal activity against monocotyledonous and dicotyledonous herbs, the crop plants of economically important crops, for example, dicotyledonous cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine , Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous cultures of the genera Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum Zea, in particular Zea and Triticum, are damaged only to an insignificant degree or are not damaged at all, depending on the structure of the respective compound according to the invention and its rate of application. It is for this reason that the compounds of the present invention are quite suitable for the selective control of the growth of unwanted plants in crop plants, such as plants useful from an agricultural point of view or ornamental plants.
In addition, the compounds according to the invention (depending on their particular structure and the rate of application used) have remarkable growth-regulating properties in crop plants. These are linked to the metabolism of the plant in a regulatory way, thus being able to be used to control the constituents of the plant and to facilitate the harvest, such as, for example, triggering desiccation and a delay in growth. Furthermore, a
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16/144 in general, they are also suitable to control and inhibit unwanted vegetative growth without destroying plants. Inhibiting vegetative growth plays an important role for many monocot and dicot crops, as, for example, this can reduce or completely prevent lodging.
Due to their herbicidal and plant growth regulation properties, the active ingredients can also be used to control harmful plants in crops of genetically modified plants or plants modified by conventional mutagenesis. In general, transgenic plants are distinguished due to their particularly advantageous properties, for example, resistance to certain pesticides, mainly certain herbicides, resistance to plant diseases or organisms that cause plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. There are other particular properties that concern, for example, the material harvested in terms of quantity, quality, storage capacity, composition and specific constituents. For example, there are known transgenic plants with a high starch content or with an altered starch quality or with a different fatty acid composition in the harvested material.
With regard to transgenic crops, it is preferable to use the compounds according to 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, soy, rapeseed, potatoes, tomatoes, peas and other vegetables. It is preferable to use the compounds according to the invention as herbicides in useful plant cultures that are resistant or that have been made resistant, by recombinant means, to the phytotoxic effects of the herbicides.
It is preferable to use the compounds according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, for example, cereals, such as wheat, barley, rye, oats, millet / sorghum, rice, cassava and corn, or sugar beet, cotton, soy, rapeseed, potatoes, tomatoes, peas and other vegetables. Preferably, the compounds according to the invention can be used as herbicides in useful plant cultures that are resistant or that have been made resistant, by recombinant means, to the phytotoxic effects of the herbicides.
Conventional methods for producing new plants that have
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17/144 properties modified compared to plants that occur to date consist, for example, of traditional culture methods and generation of mutants. Alternatively, it is possible to generate new plants with modified properties with the aid of recombinant methods (see, for example, documents EP-A-0221044, EP-A-0131624). For example, many descriptions of:
- recombinant modifications of crop plants for the purpose of modifying the starch synthesized in plants (e.g., WO 92/11376, WO 92/14827, WO 91/19806),
- transgenic crop plants that are resistant to particular herbicides of the glufosinate type (see, for example, EP-A-0242236, EPA-242246) or the glyphosate type (WO 92/00377) or the sulfonyl urea type (documents EP-A-0257993, US-A-5013659),
- transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins), which make plants resistant to particular pests (documents EP-A-0142924, EP-A-0193259),
- transgenic crop plants with a modified fatty acid composition (WO 91/13972),
- genetically modified crop plants with new constituents or secondary metabolites, for example, new phytoalexins, which provide increased resistance to disease (documents EPA 309862, EPA0464461),
- genetically modified plants with reduced photorespiration that provide higher yields and a higher tolerance to stress (document EPA 0305398),
- transgenic crop plants that produce proteins that are important from a pharmaceutical or diagnostic point of view (“molecular pharmacology”),
- transgenic crop plants that are distinguished by higher yields or better quality,
- transgenic crop plants that are distinguished by a combination, for example, of the new properties mentioned above (“gene stacking”).
There are several techniques of molecular biology through which it is possible to produce new transgenic plants with modified properties that are known in principle; 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.
To carry out such recombinant manipulations, it is possible to introduce
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18/144 nucleic acid molecules that allow mutagenesis or sequence change by recombination of DNA sequences in plasmids. With the aid of conventional methods, it is possible, for example, to perform base exchanges, to remove parts of sequences or to add natural or synthetic sequences. For the joining of DNA fragments together, it is possible to attach adapters or ligators to the fragments; see, e.g., Sambrook et a /., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker Gene und Klone, VCH Weinheim 2nd edition, 1996.
The production of plant cells with reduced activity of a gene product can be achieved, for example, by expression of at least one suitable antisense RNA or of a sense RNA to obtain a co-suppression effect or by expression of at least one properly constructed ribozyme that specifically cleaves transcripts of the aforementioned gene product. For this purpose, it is possible to use DNA molecules that comprise the entire coding sequence of a gene product including any flanking sequences present or also DNA molecules that comprise parts of the coding sequence, in which case those parts should be sufficiently large. long to produce an antisense effect on cells. The use of DNA sequences that have a high degree of homology with the coding sequences of a gene product, but which are not completely identical to it, is also possible.
When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, to achieve a location in a particular compartment, it is possible, for example, to link the coding region to DNA sequences that guarantee the location in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et a /., EMBO J. 11 (1992), 3219-3227; Wolter et a /., Proc. Natl. Acad. Sci. USA 85 (1988 ), 846850; Sonnewald et al., Plant J. 1 (1991), 95-106). Nucleic acid molecules can also be expressed in the organelles of plant cells.
The cells of transgenic plants can be regenerated by known techniques to obtain complete plants. In principle, transgenic plants can be plants of any desired plant species, that is, not only monocotyledonous plants, but also dicotyledonous plants.
Thus, it is possible to obtain transgenic plants whose properties are altered by overexpression, suppression or inhibition of genes or sequences of
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19/144 homologous genes (= natural) or expression of genes or heterologous gene sequences (= exogenous).
Preferably, the compounds of the invention can be used in transgenic cultures that are resistant to growth regulators, for example, dicamba, or to herbicides that inhibit essential plant enzymes, for example, acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydroxyphenylpyruvate dioxigenases (HPPD), or to herbicides in the group consisting of sulfonyl ureas, glyphosates, glufosinates or benzoylisoxazoles and similar active ingredients.
When using the active ingredients according to the invention in transgenic cultures, not only are the effects against harmful plants observed in other crops, but also, frequently, effects that are specific to the application in the particular transgenic culture, for example, an altered spectrum or specifically extended range of herbs that can be controlled, altered application rates that can be used for application, preferably a good combining ability with herbicides for which the transgenic culture is resistant and influencing the growth and yield of plants of transgenic cultures.
Accordingly, the invention also provides the use of the compounds of the invention as herbicides for the control of weed plants in transgenic crop plants.
The compounds according to the invention can be applied in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusting products or granules in conventional formulations. Thus, the invention also provides herbicidal and plant growth regulating compositions comprising the compounds according to the invention.
The compounds according to the invention can be formulated in different ways, according to the required biological and / or physicochemical parameters. Examples of possible formulations include: wettable powders (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil, spray solutions, suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusting products (DP), seed coating products , granules for spreading and application to the soil, granules (GR) in the form of microgranules, spray granules, granules
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20/144 coated and adsorption granules, water dispersible granules (WG), water soluble granules (SG), ULV formulations, microcapsules and waxes.
These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, Chemische Technologie [Chemical Technology], Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, Pesticide Formulations, Marcel Dekker, NY, 1973;
K. Martens, Spray Drying Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Necessary formulation aids, such as inert materials, surfactants, solvents and other additives, are also known and are described, for example, in: Watkins, Handbook of Insecticide Dust Diluents and Carriers, 2nd ed., Darland Books, Caldwell NJ, Hv Olphen, Introduction to Clay Colloid Chemistry; 2nd ed., J. Wiley & Sons, N.Y .; C. Marsden, Solvents Guide; 2nd ed., Interscience, N.Y. 1963; McCutcheon's Detergents and Emulsifiers Annual, MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, Encyclopedia of Surface Active Agents, Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, Grenzflachenaktive Athylenoxidaddukte [Interface-active Ethylene Oxide Adducts], Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, Chemische Technologie, volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Based on these formulations, it is also possible to produce combinations with other pesticide active substances, for example, insecticides, acaricides, herbicides, fungicides and also with phytoprotective agents, fertilizers and / or growth regulators, for example, under the in the form of a finished formulation or in the form of a tank mix. Suitable phytoprotective agents include, for example, mefenpyr-diethyl, cyprosulfamide, isoxadifene-ethyl, cloquintocet-mexyl and dichloromide.
Humectable powders are preparations that can be dispersed evenly in water and, together with the active ingredient, in addition to a diluent or inert substance, they also comprise ionic and / or non-ionic surfactants (wetting agents, dispersants), for example , polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycolic ether sulphates, alkane sulphonates, alkyl benzene sulphonates, sodium lignosulphonate, 2,2'-dinaftymethane-6,6'-disulfonate, sodium dibutylnaphthalene sulfonate or sodium oleoylmethyltaurate. To produce humectable powders, the herbicidal active ingredients are finely ground, for example, in conventional appliances, such as hammer mills, fan mills and air jet mills, and, simultaneously or
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Emulsifiable concentrates are produced by dissolving the active ingredient in an organic solvent, for example, butanol, cyclohexanone, dimethylformamide, xylene, or hydrocarbons or aromatics with relatively high boiling points or mixtures of organic solvents, with the addition of one or more ionic and / or non-ionic surfactants (emulsifiers). The emulsifiers used can be, for example: calcium alkylarylsulfonates, such as calcium dodecylbenzene sulfonate, or non-ionic emulsifiers, such as polyglycolic fatty acid esters, alkylaryl-polyglycolic ethers, polyglycolic ethers of fatty alcohols, oxide condensation products ethylene propylene oxide, alkyl polyethers, sorbitan esters, for example, sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example, polyoxyethylene sorbitan fatty acid esters.
The dusting products are obtained by grinding the active compound with finely distributed solid substances, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspension concentrates can be based on water or oil. They can be prepared, for example, by wet grinding using commercial ball mills and, optionally, together with the addition of surfactants, such as, for example, those already listed above for other types of formulations.
Emulsions, for example, oil-in-water (EW) emulsions, can be produced, for example, by means of agitators, colloidal mills and / or static mixers, using aqueous organic solvents and, optionally, surfactants, such as already listed before, for example, for other types of formulation.
Granules can be prepared by spraying the active ingredient onto an inert granular material capable of adsorption or by applying concentrates of the active ingredient to the surface of carrier substances, such as sand, kaolinites or inert granular materials, using adhesives, for example, alcohol polyvinyl, sodium polyacrylate or mineral oils. Suitable active ingredients can also be granulated according to the conventional method used for the production of fertilizer granules - if desired in the form of a mixture with fertilizers.
Water-dispersible granules are generally prepared by conventional processes, such as spray drying, granulation in
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22/144 fluidized bed, plate granulation, mixing with high speed mixers and extrusion without solid inert material.
For the production of food granules, fluidized bed granules, extruder granules and spray granules, see, for example, processes in Spray-Drying Handbook, 3rd ed. 1979, G. Goodwin Ltd., London, JE Browning, Agglomeration, Chemical and Engineering 1967, pages 147 ff .; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, p. 8-57.
For more details on the formulation of crop protection compositions, see, for example, GC Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, Weed Control Handbook, 5th ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
In general, agrochemical formulations contain 0.1% to 99% by weight and, in particular, 0.1% to 95% by weight of the compounds according to the invention.
In humectable powders, the concentration in active ingredient is, for example, between about 10% and 90% by weight, the remainder up to 100% by weight consisting of conventional formulation components. In the case of emulsifiable concentrates, the concentration of active ingredient is between about 1% and 90% and preferably between 5% and 80% by weight. Formulations in the form of dusting products comprise between 1% and 30% by weight of active ingredient and, preferably, normally between 5% and 20% by weight of active ingredient; sprayable solutions contain between about 0.05% and 80% and preferably between 2% and 50% by weight of active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is present in the form of a liquid or solid and on which granulation aids, fillers, etc. are used. In water-dispersible granules, the active ingredient content is, for example, between 1% and 95% by weight and preferably between 10% and 80% by weight.
In addition, the aforementioned active ingredient formulations optionally comprise the respective adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreeze agents and solvents, fillers, vehicles and dyes, defoamers, evaporation inhibitors and agents that influence conventional pH and viscosity.
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Based on these formulations, it is also possible to produce combinations with other pesticide active substances, for example, insecticides, acaricides, herbicides, fungicides and also with phytoprotective agents, fertilizers and / or growth regulators, for example, under the form of a finished formulation or tank mix.
Combination partners for the compounds according to the invention in mixing formulations or tank mixtures include, for example, known active ingredients based on the inhibition, for example, of acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshiquimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxigenase, phytoene desaturase, photosystem I, photosystem II, protoporphyrinogen oxidase, as described, for example, in Weed Research 26 (1986) 441-445 or The Pide manual, 14th edition, the British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and literature cited therein. Examples of known herbicides or plant growth regulators that can be combined with the compounds of the invention include the following active ingredients (the compounds are designated by the “common name” according to the 'International Organization for Standardization' (ISO) or by chemical name or code number) and always include all forms of use, such as acids, salts, esters and isomers, such as stereoisomers and optical isomers. As an example, a form of administration is mentioned or, in some cases, more than one form of administration:
acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfenesodium, aclonifene, alachlor, alidochlor, aloxidime, aloxidime-sodium, ametrine, amicarbazone, amidochlor, starch-sulfurone, aminopyride, amitron, amidol, sulfate atrazine, azafenidin, azimsulfurone, aziprotrin, BAH-043, BAS-140H, BAS-693H, BAS-714H, BAS-762H, BAS-776H, BAS-800H, beflubutamide, benazoline, benazoline-ethyl, bencarbazone, benfluraline, benflures bensulide, bensulfurone-methyl, bentazone, benzfendizone, benzobicyclone, benzofenap, benzofluor, benzoilprop, bifenox, bilanafos, bilanafosodium, bispiribac, bispiribac-sodium, bromacyl, bromobutide, bromophenoxide, bromoxynil, butromone, bromone, butromone butamiphos, butenachlor, butralin, butroxidime, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, clomethoxyfen, chlorambene, chlorazifop, chlorazifop-butyl, chlorobromurone, chlorofam, chlorfenac-only o, clorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimurone, chlorimuronePetition 870180133768, of 24/09/2018, p. 30/165
24/144 ethyl, chlormequat chloride, chlornitrophen, chlorophthalim, chlortal-dimethyl, chlortolurone, chlorsulfurone, cinidone, cinidone-ethyl, cinmetilina, cyino-sulfurone, cletodime, clodinafop, clodinafop-propargil, clofina, clofopopet, clofopopet, clofopopet, clofopopet, clofopopet , cloransulam, cloransulam-methyl, cumilurone, cyanamide, cyanazine, cyclanilide, cycloate, cyclo-sulfamurone, cycloxidime, cyclurone, cyhalofop, cyhalofopbutyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB , daimurone / dimrone, dalapone, daminozide, dazomet, n-decanol, demedify, desmetrine, detosyl-pyrazolate (DTP), dialate, dicamba, diclobenyl, diclorprop, dichorprop-P, diclofop, diclofopmethyl, diclofopopul-diclofop-Pul diethyl, diethyl ethyl, diphenoxurone, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefurone, dicegulacsodium, dimefurone, dimepiperate, dimetachlor, dimetamethrin, dimethenamine, dimethamine, dinetrain, dimethamine, dinetamine, dimethamine, dinetrain d ipropethrin, diquat, diquat dibromide, dithiopir, diurone, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, etalfluralin, etametsulfurone-methyl, etphone, etidimurone, ethiozine, etofumesate, ethoxy, ethoxy, ethoxy-ethoxy-ethylene-ethoxy 5331, that is, N- [2-chloro-4-fluoro-5- [4- (3-fluoropropyl) -4,5dihydro-5-oxo-1 H-tetrazol-1-yl] -phenyl] - ethane-sulfonamide, fenoprop, fenoxaprop, fenoxaprop-P, phenoxaprop-ethyl, phenoxaprop-P-ethyl, fentrazamide, phenurone, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flaza-sulfurone, florasulam, fluazifop-, fluazifop- P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, fluceto-sulfurone, flucloraline, flufenacet (thiafluamide), flufenpir, flufenpir-ethyl, flumetraline, flumetsulam, flumiclum, flumiclum, flumicloraclorum , fluometurone, fluorodifene, fluoroglycophene, fluoroglycophene-ethyl, flupoxam, flupropacil, flupropanate, flupirsulfurone, flupirsulfurone-methyl-sodium, flurenol , flurenol-butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurprimidol, flurtamone, flutiacet, flutiacet-methyl, flutiamide, fomesafene, foramsulfurone, forchlorphenurone, phosphine, furyloxin, glufin-glyphin, gliberellic acid ammonium, glufosinatoammonium, glyphosate, glyphosate-isopropyl-ammonium, H-9201, halo-sapene, halo-sulfurone, halo-sulfurone-methyl, haloxifop, haloxifop-P, haloxifop-ethoxyethyl, haloxifop-Petoxiethyl, haloxifop-methyl, haloxifop-metho P-methyl, hexazinone, HNPC-9908, HOK-201, HW-02, imazametabenz, imazametabenz-methyl, imazamox, imazapic, imazapyr, imazaquine, imazetapyr, imazo-sulfurone, inabenfide, indanophane, indanophane acid (4) -indol-3-ylbutyric (IBA), iodo-sulfurone, iodo-sulfuronamethyl-sodium, ioxynyl, isocarbamide, isopropaline, isoproturone, isourone, isoxabene, isoxaclortole, isoxaflutole, isoxapirifop, IDH-07, KUH1, KUH1, carbutylate,
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25/144 ketospiradox, lactophen, lenacil, linurone, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P-dimethyl- ammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potassium, mefenacet, mefluidide, mepiquat chloride, meso-sulfurone, meso-sulfurone-methyl, mesotrione, metabenztiazurone, metam, metamifop, metamitrone, metazachlor, metazachlor, metazachlor methoxyphenone, methyldimrone, 1methylcyclopropene, methyl isothiocyanate, metobenzurone, metobenzurone, metobromurone, metolachlor, S-metolachlor, metho-sulam, methoxyurone, metribuzin, metsulfurone, monsulfurone-monohydrate, molinate, molinate, molinate, molinate, molinate, molinate monolinurone, monosulfurone, monurone, MT-128, MT-5950, that is, N- [3-chloro-4- (1-methylethyl) -phenyl] -2methyl-pentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC -310, ie 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole, neburone, nico-sulfurone, nipyraclofene, nitral ina, nitrophen, nitrophenolate sodium (mixture of isomers), nitrofluorphene, nonanoic acid, norflurazone, orbencarb, orthosulfamurone, oryzine, oxadiargyl, oxadiazone, oxa-sulfurone, oxaziclomefone, oxifluorphon, for dichloromethane, to paclobutrazole (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlorine, pentoxazone, perfluidone, petoxamide, phenisofam, fenmedipham, fenmediphamethyl, picloram, picolinafen, pinoxadene, piperophos, pyriphenyl, primipyrone-pyriphenyl-primo , probenazole, profluazole, prociazine, prodiamine, prifluralin, profoxidime, prohexadione, prohexadione-calcium, prohydrojasmone, promethazine, promethin, propachlor, propanil, propaquizafop, propazine, profam, propisochlor, propoxycarbazone, propoxycarbazone, propoxycarbazone, propoxycarbazone, propoxycarbazone, propoxycarbazone , prosulfaline, pro-sulfocarb, pro-sulfurone, prinachlor, pyraclonyl, piraflufene, piraflufene-ethyl, pyra-sulfotole, pyrazolinate (pyrazolate), p irazo-sulfurone-ethyl, pyrazoxifene, pyribambenz, pyribambenz-isopropyl, pyribenzoxime, pyributicarb, pyridafol, pyridate, pyriftalide, pyriminobac, pyriminobac-methyl, pyrimisulfan, piritiobac, piritiobac-sodium, piroxa-sulfone, quiroxa-sulfone, quiroxa-sulfone, quiroxamine quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuril, rimsulfurone, secbumetone, setoxidime, sidurone, simazine, symmetrine, SN-106279, sulcotrone, sulfentone, sulfometrazine , sulfometurone-methyl, sulfosate (glyphosate-trimesium), sulfo-sulfurone, SYN-523, SYP-249, SYP-298, SYP-300, tebutam, tebutiurone, tecnazene, tefuriltrione, tembotrione, tepraloxidime, terbacyl, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb, terbucarb. terbumetone, terbuthylazine, terbutrin, TH-547, tenylchlorine, thiafluamide, thiazaflurone, thiazopyr,
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26/144 tidiazimine, thidiazurone, thiencarbazone, thiencarbazone-methyl, thifensulfurone, tifensulfurone-methyl, thiobencarb, thiocarbazil, topramezone, tralcoxidime, trialate, tria-sulfurone, triaziflamine, triazylamide, triazyl, triazyl, triazyl, triazyl, triazyl , tridifan, trietazine, trifloxy-sulfurone, trifloxysulfurone-sodium, trifluralin, triflu-sulfurone, triflu-sulfurone-methyl, trimeturone, trinexapac, trinexapac-ethyl, trito-sulfurone, tsitodef, uniconazole, Zonole, uniconazole, , ZJ-0270, ZJ-0543, ZJ-0862 and the following compounds:
h ₃ c
For application, formulations present in a commercial form are, if appropriate, diluted in a conventional manner, for example, with water, in the case of humectable powders, emulsifiable concentrates, dispersions and water-dispersible granules. Preparations in the form of dusting products, granules for application to the soil or granules for spreading and sprayable solutions are normally no longer diluted with other inert substances before application.
The required application rate for the compounds of formula (I) varies with external conditions, including temperature, humidity and the type of herbicide used. It can vary in wide limits, for example, between 0.001 and 1.0 kg / ha or more of active substance; however, they are preferably between 0.005 and 750 g / ha.
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The following examples illustrate the invention.
A. Chemical examples
Synthesis of N-ethyl-2-methyl-3- (methylsulfonyl) -N- (1-methyl-1 H-tetrazol-5-yl) -4 (trifluoromethyl) -benzamide (table, example No. A-2)
100 mg (0.275 mmol) of 2-methyl-3- (methylsulfonyl) -N- (1-methyl-1Htetrazol-5-yl) -4- (trifluoromethyl) -benzamide and 43 mg (0.275 mmol) of iodoethane are dissolved in 5 ml of N, N-dimethylformamide and 0.038 mg (0.275 mmol) of potassium carbonate are added. The reaction mixture is stirred at 80 ° C for 16 hours, taken up in 5 ml of water and extracted twice with 10 ml of dichloromethane each time. Dry the organic phase over Na ₂ SO4 and concentrate. The residue is purified by means of preparative HPLC (acetonitrile, water). Yield 30 mg (26%).
¹ H NMR (400 MHz; CDCla): 7.96 ppm (d, 0.5H); 7.7 ppm (d, 0.5H), 7.67 (d, 0.5H), 7.38 (d; 0.5H); 4.10-3.61 (m, 5H); 3.28 (s, 1.5H); 3.18 (s, 1.5H); 2.83 (s, 3H); 1.32 (t; 1.5H), 1.11 (s; 1.5H).
Synthesis of 2-chloro-3- [5- (cyanomethyl) -4,5-dihydro-1,2-oxazol-3-yl] -4 (ethylsulfonyl) -N- (1-methyl-1H-tetrazole- 5-yl) -benzamide (table, example No. A12)
178 mg (0.5 mmol) of 2-chloro-3- [5- (cyanomethyl) -4,5-dihydro1,2-oxazol-3-yl] -4- (ethylsulfonyl) -benzoic acid and 90 mg (0.65 mmol) of N-allyl-1-methyl-1Htetrazol-5-amine in 3 ml of pyridine at room temperature (RT) for 1 hour and then a solution of 86 mg (0.675 mmol) is added ) of oxalyl chloride in 2 ml of dichloroethane. Subsequently, the mixture is stirred at 75 ° C for 4 hours. After cooling to room temperature, 0.5 ml of water is added. Then, the mixture is stirred at room temperature for 30 minutes. The reaction solution is filtered and concentrated. The residue is purified by means of preparative HPLC (acetonitrile / water). Yield: 19 mg (8%).
¹ H NMR (400 MHz; DMSO-d6): 8.23; 8.15; 7.90 and 7.82; (4d, 2 H); 5.88 (m, 1H), 5.42 - 4.98 (m, 3H), 4.55 (s lr., 1H), 4.29 (d, 1H), 4.10 and 4.04 ( 2s, 3H), 3.67 2.98 (m, 7H), 1.18 and 1.04 (2t, 3H).
Synthesis of methyl [2- (methylsulfonyl) -4- (trifluoromethyl) -benzoyl] - (1-methyl-1H-tetrazol-5yl) -carbamate (table, example No. A14)
To a solution of 175 mg (0.5 mmol) of 2- (methylsulfonyl) -N- (1-methyl-1Htetrazol-5-yl) -4- (trifluoromethyl) -benzamide in 4 ml of THF (abs.), in a protective gas environment and at 0 ° C, 14 mg (0.55 mmol) of sodium hydride (a
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95%). After stirring for 10 minutes, 46 µL (0.6 mmol) of methyl chloroformate is added at 0 ° C. The reaction mixture is stirred at room temperature for 1 hour. Subsequently, the pH of the reaction mixture is adjusted to pH 7 with a saturated aqueous solution of sodium hydrogen carbonate and 10 ml of water are added. Then, the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated. Yield: 231 mg (57%).
¹ H NMR (400 MHz; DMSO-d6): 8.40 (s, 1H), 8.31 (d, 1H), 8.15 (d, 1H), 4.14 (s, 3H), 3, 67 (s, 3H); 3.38 (s, 3H).
Synthesis of N-allyl-2-methyl-N- (4-methyl-1,2,5-oxadiazol-3-yl) -3- (methylsulfonyl) -4 (trifluoromethyl) -benzamide (when, example No. C -1)
150 mg (0.413 mmol) of 2-methyl-N- (4-methyl-1,2,5-oxadiazol-3-yl) 3- (methylsulfonyl) -4- (trifluoromethyl) -benzamide and 50 mg ( 0.413 mmol) of allyl bromide in 5 mL of N, N-dimethylformamide and 0.057 mg (0.413 mmol) of potassium carbonate are added. The reaction mixture is stirred at 80 ° C for 8 hours, taken up in 5 ml of water and extracted with 10 ml of dichloromethane each time. Dry the organic phase over Na2SO4 and concentrate. The residue is purified by means of preparative HPLC (acetonitrile, water). Yield 160 mg (86%).
¹ H NMR (400 MHz; DMSO-d6): 8.10-8.01 ppm (lr., 1H); 7.84 ppm (d, 0.5H), 7.75 (d, 0.5H), 7.38 (d, 0.5H); 5.98-5.75 (m, 1H); 5.38 (d, 0.5H); 5.26 (d, 0.5H); 5.14 (d, 0.5H); 5.02 (d, 0.5H); 4.19 (d, 2H); 3.46 (s, 1.5H); 3.30 (s; 1.5H), 2.89 (s; 1.5H); 2.70 (s, 1.5H); 2.43 (s, 3H).
Synthesis of N-methyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) -2-methyl-3- (methylsulfonyl) -4 (trifluoromethyl) -benzamide (table, example No. D1 )
180 mg (0.495 mmol) of 2-methyl-N- (5-methyl-1,3,4-oxadiazol-2-yl) 3- (methylsulfonyl) -4- (trifluoromethyl) -benzamide are dissolved in 6 ml of DMF (abs.) And 68 mg (0.495 mmol) of K2CO3 and 0.047 mL (0.495 mmol) of dimethyl sulfate are added. The reaction mixture is boiled at reflux for 15 hours. Then, the mixture is filtered, the filtrate is concentrated and purified by column chromatography (silica gel; heptane / ethyl acetate).
¹ H NMR (400 MHz; CDCla): 7.98 (d, 1H), 7.49 (d, 1H), 3.57 (s lr, 3H), 3.23 (s, 3H), 2.92 (s, 3H), 2.37 (s, 3H).
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The examples presented in the following tables were prepared in a manner analogous to the aforementioned methods or were obtained in a manner analogous to the aforementioned methods. The compounds specified in the following tables, Tables 1 to 336, which are obtained in a manner analogous to the 5 methods specified herein, are particularly preferred.
The abbreviations used refer to:
Et = ethyl Me = methyl n-Pr = n-propyl i-Pr = isopropyl c-Pr = cyclopropyl Ph = phenyl Bn = benzyl Prg = propargyl
Table 1: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2,2,2- trifluoroethoxy) -methyl, the symbol V represents hydrogen and the symbol Z represents methylsulfonyl.
At the. R Physical data ( ¹ H NMR, DMSO-d6, 400 MHz) 1-1 Me1-2 Et1-3 i-Pr1-4 CH2CHF21-5 CH2CF31-6 CH2OMe1-7 CH2OEt1-8 CH2OPh1-9 CH2SMe1-10 CH2SEt1-11 CH2SPh1-12 CH2SO2Me1-13 CH2CH2CN1-14 CH2CH2OMe1-15 CH2CH2OEt1-16 CH2CH2OPh
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At the. R Physical data ( ¹ H NMR, DMSO-d6, 400 MHz) 1-17 CHzCHzSMe1-18 CH2CH2S (O) Me1-19 CH2CH2SO2Me1-20 CH2CH2SEt1-21 CH2CH2S (O) Et1-22 CH2CH2SO2Et1-23 CH2CH2SPh1-24 CH2CH2S (O) Ph1-25 CH2CH2SO2Ph1-26 CH2C (O) Me1-27 CH2C (O) Ph1-28 CH2CO2He1-29 CH2CO2Me1-30 CH2CO2Et1-31 CH2CN1-32 CH2CH2CN1-33 ally1-34 Prg1-35 benzyl1-36 CO2Me1-37 CO2Et1-38 CO2-iPr1-39 CO2CH2-CHMe21-40 CO2CH2-t-Bu
Table 2: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2,2,2- trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 3: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 4,5-dihydro -1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
N'O „ ⁿ -no
N K jí
Cl
Table 4: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 4,5-dihydro -1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
nO zN'N o
N jí K
Cl
Table 5: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5 -dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Cl N-O, n-n o
N í jí
CN
Table 6: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 5- (methoxymethyl) -4 , 5-dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 7: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methoxymethyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
// O
Table 8: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethoxymethyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 9: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2-methoxyethoxy) -methyl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
O
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Table 10: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 11: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methoxy, the symbol V represents hydrogen , the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 12: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Cl O
Me
Table 13: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol 5 represents CY, the symbol Y represents ethoxy, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 14: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Et
Table 15: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents allyloxy, the symbol V represents
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hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 16: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 2-fluoroethoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Cl o
Me
Table 17: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents propoxy, the symbol V represents hydrogen , the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 18: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents propoxy, the symbol V represents
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Table 19: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (3-methylsulfanyl) -propoxy , the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 20: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2-methylsulfanyl) -ethoxy , the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 21: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents cyclopropylmethoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 22: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents cyclopropylmethoxy, the symbol V represents hydrogen , the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 23: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2-dimethylamino) -2 -oxoethoxy, the symbol V represents hydrogen, the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
Table 24: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methoxycarbonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 25: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (ethoxyimino) -methyl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 26: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 1- (ethylamino) -1 -oxopropane-2yl] -amino, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 27: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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Me
Table 28: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 29: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Cl n—
Et
Table 30: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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O
S-
O
Cl
Me
Table 31: compounds of the invention of formula (I), in which the symbol represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol represents hydrogen, the symbol meaning defined in Table 1:
represents chlorine and the R symbol has
O w n—
Cl
Et
Table 32: compounds of the invention of formula (I), in which the symbol represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol represents hydrogen, the symbol meaning defined in table 1:
represents methyl and the symbol R has s—
Me
Me
Table 33: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Z represents methyl and the symbol R has the
Cl n—
Me
Me
Table 34: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Me
Table 35: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Et
Table 36: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
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Me
Table 37: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Et
Table 38: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 39: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Et
Table 40: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
ci so Et
Me
Table 41: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Me
Table 42: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
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O
Me
Me
Table 43: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Me
Table 44: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Me
Table 45: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the
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c.i sn Et
R
Me
Table 46: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 2-methoxyethylsulfinyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in table 1:
Table 47: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the meaning symbol defined in Table 1:
represents methyl and the symbol R has
Br
Me
Me
Table 48: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the
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Me
Table 49: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the meaning symbol defined in Table 1:
represents methyl and the symbol R has
O
S-
Me
Me
Table 50: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the meaning symbol defined in Table 1:
represents methyl and the symbol R has
Me
Table 51: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V
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Z represents methyl and the symbol R has the
O
Me
Table 52: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol represents hydrogen, the meaning symbol defined in table 1:
represents methyl and the symbol R has
O
s
Me
Me
Table 53: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 54: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V
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Table 55: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 4,5-dihydro -1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 56: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 4,5-dihydro -1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 57: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents (cyclopropylmethyl) -amino, the symbol V represents hydrogen, symbol Z represents methylsulfonyl and symbol R has the meaning defined in table 1:
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Table 58: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents propylamino, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 59: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 60: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 61: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 62: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 63: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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N
Table 64: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
n ^x n
Table 65: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
/ N ^ N 'n
Table 66: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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N 'N
Table 67: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
/ N.
n
Table 68: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
Me
Table 69: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
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Me
Table 70: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
Me
Table 71: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents iodine and the symbol R has the meaning defined in Table 1:
Me
Table 72: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the Z symbol represents iodine and the R symbol has the
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Me
Table 73: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the meaning symbol defined in Table 1:
Z represents iodine and the symbol R has
O
s-
I
Me
Table 74: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol Y represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents iodine and the symbol R has the meaning defined in Table 1:
Table 75: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V
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S-
Table 76: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 77: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents n-propyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in table 1:
Table 78: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents allyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V
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Table 79: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents ethyl; the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
xN.
Kl '
Table 80: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 81: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
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Table 82: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents n-propyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in table 1:
Table 83: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methoxymethyl; the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol
R has the meaning defined in Table 1:
Table 84: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents allyl; the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 85: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents propargyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 86: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 87: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
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Table 88: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol Y represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
Me
Table 89: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
n 'N
F
Table 90: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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N 'N
Table 91: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
n ^x n
F
Table 92: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 93: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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Table 94: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N ^x N
F
Table 95: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 96: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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N
O
SO ₂ Et
N Et
Cl
Table 97: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 2-methoxyethylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 98: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
Table 99: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents n-propyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 100: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
Table 101: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents ethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 102: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents ethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
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Table 103: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
Table 104: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
Table 105: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents n-propyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 106: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 107: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents ethyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 108: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
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Table 109: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 110: compounds of the invention of formula (I), where the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents ethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
Table 111: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 112: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents ethyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has
Table 113: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 114: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents CY, the symbol Y represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents bromine and the symbol R has the meaning defined in Table 1:
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Table 115: compounds of the invention of formula (I), where Q represents Q1, R ⁶ represents methyl, X represents n-propyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has
Table 116: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents isopropyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 117: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents cyclopropyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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// ⁿ ^ n
Me
Table 118: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 119: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 120: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 121: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 122: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 123: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 124: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 125: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents ethyl, X represents ethoxy; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 126: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 127: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Me'
Table 128: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Me'
Table 129: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents hydrogen, the symbol V represents methyl, the symbol Z represents methylsulfanyl and the symbol R has the meaning defined in Table 1:
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Table 130: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents methyl, the symbol Z represents hydrogen and the symbol R has the meaning defined in Table 1:
Table 131: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents methyl, the symbol Z represents hydrogen and the symbol R has the meaning defined in Table 1:
Me ^z
Table 132: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methyl; the symbol V represents methyl, the symbol Z represents methylsulfanyl and the symbol R has the meaning defined in Table 1:
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Table 133: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 134: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents chlorine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents methylsulfanyl and the symbol R has the meaning defined in Table 1:
Table 135: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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N
N
Me
N
R
SO ₂ Me
Table 136: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 137: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents methylsulfanyl and the symbol R has the meaning defined in Table 1:
Table 138: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methylsulfonyl; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 139: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 140: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 141: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents (methylsulfanyl) -methyl; the symbol W represents CY, the symbol Y represents hydrogen; the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 142: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol R ⁶ represents methyl, the symbol X represents chlorine; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 143: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents bromine; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N
N
Table 144: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methyl; the symbol W represents N; the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N
N
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Table 145: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methylsulfonyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N
II
N
Table 146: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents methoxymethyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 147: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents ethyl, X represents methoxymethyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 148: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents ethyl, X represents (2-methoxyethyl) methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 149: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents (3methoxypropyloxy) methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N
II N
Table 150: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents (cyclopropylmethoxy) -methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
N
II
N
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Table 151: compounds of the invention of formula (I), wherein Q represents Q1, R ⁶ represents methyl, X represents (methylsulfanyl) -methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Q = Q2 triazoles
Table 152: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents nitro; the symbol W represents CY, the symbol Y represents hydrogen, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 153: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents hydrogen, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 154: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methylsulfonyl; the symbol W represents CY, the symbol Y represents hydrogen, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 155: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 156: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxymethyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 157: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents (2 methoxyethoxy) -methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 158: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents (2,2,2-trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 159: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5-dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in table 1:
Table 160: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 4,5-dihydro-1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1 :
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Table 161: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 5- (methoxymethyl) -4,5-dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 162: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Table 163: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
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Table 164: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 165: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents chlorine and the symbol R has the meaning defined in Table 1:
Table 166: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 167: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V
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Table 168: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 169: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 170: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 171: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 172: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 2-methoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 173: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents propoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 174: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents cyclopropylmethoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 175: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 2-methoxyethoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 176: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methoxymethyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 177: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents (2-methoxyethoxy) -methyl, the
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R has the meaning defined in Table 1:
Table 178: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents chlorine, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 179: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents (tetrahydrofuran-2-ylmethoxy) methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 180: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 2-fluoroethoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 181: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents (3-methoxy) -propoxy, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 182: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Table 183: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
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Table 184: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents bromine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Table 185: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents methyl; the symbol W represents CY, the symbol Y represents 4,5-dihydro-1,2-oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 186: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 187: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Table 188: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 189: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 190: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 191: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 192: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents methyl; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 193: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methyl; the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 194: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 195: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 196: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 197: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol R ⁷ represents methyl, the symbol X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Table 198: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 199: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxy; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 200: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 201: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 202: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents methoxymethyl; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 203: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents ethyl; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 204: compounds of the invention of formula (I), wherein Q represents Q2, R ⁷ represents methyl, X represents trifluoromethyl; the symbol W represents CY, the symbol Y represents 2-methoxyethoxy, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
Table 205: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 206: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl; the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 207: compounds of the invention of formula (I), in which the symbol Q
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Table 208: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents (2,2,2-trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 209: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 1H-1,2,3-triazol-1-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 210: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 211: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 212: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 4-methyl-1H-pyrazol-1-yl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 213: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 214: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 215: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 216: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 217: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 218: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 219: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 220: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Table 221: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 222: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 223: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 224: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 225: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 226: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 227: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methoxymethyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
MeO
Table 228: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5-dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in table 1:
Table 229: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methoxy, the symbol X represents chlorine; the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5-dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in table 1:
Table 230: compounds of the invention of formula (I), in which the symbol Q
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Table 231: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 232: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 233: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents 1H-pyrazol-1-yl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 234: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 235: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 236: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 237: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 238: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 239: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 240: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents cyclopropyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V
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Table 241: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents (2-methoxyethyl) -sulfonyl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 242: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents (2-methoxyethyl) -sulfonyl , the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 243: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 244: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 245: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 246: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents amino, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 247: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents acetylamino, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 248: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methoxy, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 249: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 250: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 251: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 252: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 253: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
MeO
Table 254: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents 1H-1,2,4-triazol-1-yl, the symbol X represents methyl, the symbol W represents CY , the symbol Y represents methylsulfinyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 255: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 256: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the
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Table 257: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methylsulfanyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol
R has the meaning defined in Table 1:
Table 258: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents nitro, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 259: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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MeO
Table 260: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents (1H-pyrazol-1-yl) -methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, symbol V represents hydrogen, symbol Z represents trifluoromethyl and symbol R has the meaning defined in table 1:
Table 261: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents acetylamino, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 262: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents (2,2-dimethylpropanoyl) -amino, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 263: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methyl, the symbol Y represents CY, the symbol Y represents ethylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 264: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents chlorine, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents ethylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 265: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents ethyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 266: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 267: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 268: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 269: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 270: compounds of the invention of formula (I), where the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 271: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 272: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol
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R has the meaning defined in Table 1:
Table 273: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 274: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 275: compounds of the invention of formula (I), in which the symbol Q represents Q3, the symbol R ⁸ represents methyl, the symbol X represents trifluoromethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 276: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in table 1:
Table 277: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in table 1:
Table 278: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents N, the symbol V represents hydrogen, the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in table 1:
MeO ^N o
Cl
^CF 3
Table 279: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methoxymethyl,
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N-n
CHOMe
Et
Table 280: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents hydrogen, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2,2,2- trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
N-n
Cl ^CF 3
SO ₂ Me
Table 281: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2,2,2- trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
N-n
Cl
Me
SO ₂ Me ^CF 3
Table 282: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents isopropyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents (2,2,2- trifluoroethoxy) -methyl, the symbol V represents hydrogen, the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 283: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents propoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 284: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents cyclopropylmethoxy, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 285: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5 -dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 286: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents 5-cyanomethyl-4,5 -dihydro-1,2oxazol-3-yl, the symbol V represents hydrogen, the symbol Z represents ethylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 287: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 288: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 289: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Table 290: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 291: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 292: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 293: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 294: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 295: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 296: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 297: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 298: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 299: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V
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Me
Table 300: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Et
Table 301: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 302: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Me
Table 303: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Et
Table 304: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents chlorine, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 305: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents fluorine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 306: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Table 307: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents bromine, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methyl and the symbol R has the meaning defined in Table 1:
Table 308: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 309: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Table 310: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol
R has the meaning defined in Table 1:
Table 311: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 312: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents cyclopropyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 313: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents trifluoromethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 314: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 315: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
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Table 316: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol
R has the meaning defined in Table 1:
Table 317: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Table 318: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents trifluoromethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol
R has the meaning defined in Table 1:
Table 319: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents 2,2,2-trifluoroethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl , O
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R has the meaning defined in Table 1:
Table 320: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 321: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 322: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 323: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Me
Table 324: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 325: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 326: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 327: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents ethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 328: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methoxymethyl, the symbol X represents methyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 329: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V
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Me
Table 330: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 331: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents trifluoromethyl and the symbol R has the meaning defined in Table 1:
Me
Table 332: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 333: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 334: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxy, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
Table 335: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfanyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol R has the meaning defined in Table 1:
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Table 336: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfinyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
Table 337: compounds of the invention of formula (I), where the symbol Q represents Q4, the symbol R ⁹ represents methyl, the symbol X represents methoxymethyl, the symbol W represents CY, the symbol Y represents methylsulfonyl, the symbol V represents hydrogen , the symbol Z represents methylsulfonyl and the symbol
R has the meaning defined in Table 1:
More particularly preferred are compounds of formula shown in Tables A, B, C and D, which can be obtained in a manner analogous to the methods specified herein.
Table A: compounds of the invention of formula (I), in which the symbol Q represents Q1, the symbol V represents hydrogen and each of the symbols R, R ⁶ , X, W, Z and V has the meaning defined in table A
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No. R R ⁶ X W Z Physical data (1H NMR,DMSO-d6, 400 MHz) TO 1 CH2OEt Me Me C-SO2Me CF3 7.94; 7.78; 7.67 and 7.42; (4d,2H); 5.33 and 4.90 (2s lr., 2H), 4.08 and 4.00 (2s, 3H), 3.86-3.72 and 3.41-3.16 (2m, 5H), 2 , 88 and2.85 (2s, 3H), 1.31-1.02 (m, 3H) A-2 Et Me Me C-SO2Me CF3 7.98; 7.69; 7.67 and 7.37; (4d, 2H); 4.11-3.58 (m, 5H), 3.28 and3.3.18 (2s, 3H), 3.83 (s, 3H),1.32 and 1.12 (2t, 3H) A-3 Me Me Me C-SO2Me CF3 7.98, 7.69, 7.38 (3d lr., 2H),4.07, 3.91 (2s lr., 3H), 3.51,3.37 (2s lr., 3H), 3.28, 3.20 (2slr., 3H), 2.84 (s, 3H) A-4 Bn Me Me C-SO2Me CF3 8.23, 8.05, 7.80, 7.76 (4d, 2H), 7.41-7.11 (m, 5H), 5.12, 4.83 (2s lr., 2H), 4 , 02, 3.96 (2s, 3H),3.34 (s, 3H), 2.68, 2.52 (2s, 3H) A-5 Me Bn Me C-SO2Me CF3 8.06, 7.89, 7.61.7.18 (4d, 2H), 7.43-7.29 (m, 5H), 5.73, 5.66 (2s lr., 2H), 3 , 46, 3.42 (2s, 3H),3.34, 3.13 (2s, 3H), 2.70, 2.65 (2s, 3H) A-6 Prg Me Me C-SOMe CF3 7.79-7.25; (m, 2H); 5.31 (s lr.,2H), 3.95 (s, 3H), 2.96 (2s, 6H)
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No. R R ⁶ X W Z Physical data (1H NMR,DMSO-d6, 400 MHz) A-7 CH2CO2Me Me Me C-SOMe CF3 7.72; 7.59; 7.46 and 7.31; (4d, 2H); 5.02-4.93 and 4.60-4.31 (2m, 2H), 4.19 and 3.69 (2s, 3H),3.82 (s, 3H), 3.01 (s, 3H), 2.97 (s, 3H) A-8 CH2CO2Me Me Me C-SO2Me CF3 7.94; 7.72; 7.68 and 7.47; (4d, 2H); 4.80-4.33 (m, 2H), 4.19;3.91; 3.84 and 3.69 (4s, 6H), 3.38 and 3.33 (2s, 3H), 2.90 and 2.82 (2s, 3H) A-9 ally Me Me C-SO2Me CF3 7.95; 7.69; 7.66 and 7.40; (4d, 2 H); 5.99-5.87 and 5.79-5.65 (2m, 1H), 5.33; 5.32; 5.19 and 5.01 (4d, 2H), 4.61 - 4.13 (m, 2H), 4.05 and 3.85 (2s, 3H), 3.28 and3.19 (2s, 3H), 2.91 and 2.85 (2s, 3H), A-10 Prg Prg Cl C-Cl SO2Me 8.02; (d, 1H); 7.67 (d, 1H), 5.60 (s lr., 2H), 4.86 (s lr., 2H), 3.52 (b, 1H), 3.43 (s, 3H), 3 , 34 (t, 1H) A-11 Me Me Me C-SO2Me SO2Me 8.29; 8.12; 8.02; 7.75 (4db, 2H); 3.67-3.54 (m, 6H); 3.46;3.25 (2s, 3H); 2.70; 2.64 (2s,3H), 2.47; 2.42 (2s, 3H) A-12 ally Me Cl C- (4,5-dihydro-5-cyano-1,2oxazol) -4-yl SO2Et 8.23; 8.15; 7.90 and 7.82; (4d, 2H); 5.88 (m, 1H), 5.42 - 4.98 (m, 3H), 4.55 (s lr., 1H), 4.29 (d, 1H), 4.10 and 4.04 ( 2s, 3H), 3.67 - 2.98 (m, 7H), 1.18 and 1.04 (2t, 3H)
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No. R R ⁶ X W Z Physical data ('H NMR,DMSO-d6, 400 MHz) A-13 Me CO2Me Cl C-OH SO2Me 9.39 (s lr., 1H), 7.80 (d, 1H),7.16 (d, 1H), 4.08 (s, 3H), 3.21 (s, 3H), A-14 Me CO2Me SO2Me C-H CF3 8.40 (s, 1H), 8.31 (d, 1H), 8.15 (d, 1H), 4.14 (s, 3H), 3.67 (s, 3H); 3.38 (s, 3H), A-15 Me CO2Et SO2Me C-H CF3 1H-NMR (400 MHz; DMSO-d6):8.40 (s, 1H), 8.32 (d, 1H), 8.16 (d, 1H), 4.13 (s, 3H), 4.10 (q,2H); 3.38 (s, 3H), 0.93 (t, 3H), A-16 Me CO2-i-Pr SO2Me C-H CF3 8.39 (s, 1H), 8.32 (d, 1H), 8.18(d, 1H), 4.81 (m, 1H), 4.12 (s,1H), 3.38 (s, 3H); 0.95 (d, 6H) A-17 Me CO2CH2CHMe2 SO2Me C-H CF3 8.40 (s, 1H), 8.31 (d, 1H), 8.19 (d, 1H), 4.14 (s, 3H), 3.88 (d,2H), 3.38 (s, 3H); 1.62 (m, 1H),0.62 (d, 6H) A-18 Me CO2CH2-t-Bu SO2Me C-H CF3 8.40 (s, 1H), 8.32 (d, 1H), 8.22(d, 1H), 4.15 (s, 3H), 3.38 (s,3H); 0.63 (s, 9H)
Table B: compounds of the invention of formula (I), in which the symbol Q represents Q2, the symbol V represents hydrogen and each of the symbols R, R ⁷ , X, W and Z has the meaning defined in table A
No. R R ⁷ X W Z Physical data ('H NMR,DMSO-d6, 400 MHz) B-1
Table C: compounds of the invention of formula (I), where the symbol Q
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At the. R R ⁸ X W Z Physical data (1H NMR, DMSO-d6, 400 MHz) C-1 ally Me Me C-SO2Me CF3 8.10-8.01 (lr., 1 H); 7.83; 7.74 (2d, 1H); 5.98-5.75 (m, 1H); 5.38; 5.26 (2d, 1H); 5.14; 5.02 (2d,1H); 4.19 (d, 2H); 3.46; 3.30 (2s; 3H), 2.89; 2.72 (2s; 3H); 2.43 (s, 3H) C-2 CH2CH2CN Me Me C-SO2Me CF3 8.12; 8.11; 7.87; 7.72 (4d, 2 H); 4.01-3.82 (m, 2H), 3.49-3.37 (m, 3H); 2.99-2.79 (m, 2H), 2.72 (s, 3H), 2.42; 2.41 (2s, 3H) C-3 Prg Me Me C-SO2Me CF3 8.07; 7.83; 7.7.4; (3d, 2 H); 4.48; 4.44 (2s lr.,2H), 3.46; 3.34 (2s, 3H); 3.74; 3.69 (2s, 3H);2.43 (s, 3H) C-4 CH2CO2Me Me Me C-SO2Me CF3 8.85; 7.68; (2d, 2 H); 4.74 (br s, 2H), 3.76; 3.46(2s, 3H); 3.42; 3.39 (2s, 3H), 2.74; 2.72 (2s, 3H),2.42; 2.38 (2s, 3H) C-5 Me Me Me C-SO2Me SO2Me 8.29; 8.12; 8.02; 7.75 (4d lr., 2 H); 3.67-3.54 (m,6H); 3.46; 3.25 (2s, 3H); 2.70; 2.64 (2s, 3H),2.47; 2.42 (2s, 3H) C-6 CH2OEt Me Me C-SO2Me CF3 8.07 (s lr., 1H), 7.85 and 7.77 (2bs, 1H), 5.35 and 4.89 (2s lr., 2H), 3.70 and 3.33 (2 s lr ., 3H), 3.42 (q lr., 2H), 2.71 (s, 3H), 2.42 (s, 3H), 2.66 and 2.55 (2s, 3H), 2.36 (s, 3H) C-7 Bn Me Me C-SO2Me CF3 8.14, 8.02, 7.82 and 7.76 (4d, 2H), 7.40 - 7.08 (m, 5H), 5.25 and 4.82 (2s lr., 2H), 3 , 32 (s, 3H), 1.17 and 1.01 (2t, 3H).
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At the. R R ⁸ X W Z Physical data ( ¹ H NMR, DMSO-d6, 400 MHz) C-8 Me Me Me C-SO2Me CF3 BCAK20931-1-1 ¹ H NMR (400 MHz; DMSO-d6): 7.96, and 7.36 (2s lr., 1H), 7.68 (s lr., 1H), 3.48-3, 19 (4s, 6H), 2.82 (s lr., 3H), 2.45 and 2.34 (2s lr., 3H) C-9 Me Et Me C-SO2Me CF3 7.95 and 7.35 (d lr., 1H), 7.68 (s lr., 1H), 3.48, 3.30,3.27 and 3.19 (4s lr., 6H), 2.82 - 2.66 (m, 5H), 1.38 (t, 3H), C-10 Me Cl Cl C-S (O) Me CF3 7.84 - 7.52 (m, 2H), 3.63 - 3.32 (m, 3H), 3.24 -2.96 (m, 3H), C-11 Prg Cl Cl C-SMe CF3 7.70 (s lr., 1H), 7.50 (s lr., 1H), 4.80 (s lr., 2H),2.45 - 2.33 (m, 4H), C-12 Prg Me Me C-SO2Me SO2Me 8.41, 8.16, 7.81 and 7.45 (4s lr, 2H), 4.73 and 4.37 (2s lr, 2H), 3.57 - 3.42 (m, 6H), 2 , 87 - 2.77 (s lr., 3H), 2.44 - 2.34 (m, 4H) C-13 Me Cl Cl C-SMe CF3 7.68 and 7.49 (2s lr., 2H), 3.50 (s lr., 3H), 2.33 (s lr., 3H).
Table D: compounds of the invention of formula (I), in which the symbol Q represents Q4, the symbol V represents hydrogen and each of the symbols R, R ⁹ ,
X, W and Z have the meaning defined in table A
No. R R ⁹ X W Z Physical data ( ¹ H NMR, CDCh, 400 MHz) D-1 Me Me Me C-SO2Me CF3 7.98 (d, 1H), 7.49 (d, 1H), 3.57 (s lr., 3H),3.23 (s, 3H), 2.92 (s, 3H), 2.37 (s, 3H).
B. Formulation examples
a) A dusting product is obtained by mixing 10 parts by weight of a compound of formula (I), and / or its salts, and 90 parts by weight of talc, as an inert substance, and comminution of the mixture in a hammers.
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b) A water-dispersible humectable powder is obtained by mixing 25 parts by weight of a compound of formula (I), and / or its salts, 64 parts by weight of quartz containing kaolin, as an inert substance, 10 parts in weight of potassium lignosulfonate and 1 part by weight of sodium oleoylmethyltaurate, as a wetting and dispersing agent, and grinding the mixture in a pin disc mill.
c) A water-dispersible dispersion concentrate is obtained by mixing 20 parts by weight of a compound of formula (I), and / or its salts, with 6 parts by weight of polyphenolic alkylphenol ether (© Triton X 207) , 3 parts by weight of polyglycolic isotridecanol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, between about 255 ° C and above 277 ° C), and grinding the mixture in one ball mill to a fineness of less than 5 microns.
d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of formula (I), and / or its salts, 75 parts by weight of cyclohexanone, as a solvent, and 10 parts by weight of ethoxylated nonylphenol , as an emulsifier.
e) Water-dispersible granules are obtained by mixing parts by weight of a compound of formula (I), and / or its salts, parts by weight of calcium lignosulphonate, parts by weight of sodium lauryl sulphate, parts by weight of polyvinyl alcohol and parts by weight and kaolin, grinding the mixture in a pin disc mill and granulating the powder in a fluidized bed by applying a spray of water as a granulation liquid.
f) Water-dispersible granules are also obtained by homogenization and pre-comminution of parts by weight of a compound of formula (I), and / or its salts, parts by weight of 2,2'-dinaftymethane-6.6 ' -sodium disulfonate, parts by weight of sodium oleoylmethyltaurate, part by weight of polyvinyl alcohol,
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C. Biological examples
1. Pre-emergence herbicidal action against harmful weed plants
Seeds of monocotyledonous and dicotyledonous herb plants and crop plants are placed in wooden fiber pots on sandy soil and covered with soil. The compounds of the invention, formulated in the form of wettable powders (WP) or emulsion concentrates (EC), are then applied to the surface of the covering soil, in the form of an aqueous suspension or emulsion at an application rate of 600 to 800 L / ha water (converted) with the addition of 0.2% wetting agent. After the treatment, the pots are placed in a greenhouse and maintained under good growth conditions for the plants under test. Test plant damage is visually assessed after a 3-week test period by comparison with untreated controls (percentage herbicidal activity (%): 100% action = plants have died, 0% action = same as plants of control). For example, each of the compounds paragraphs A-2, A-3, A-4, A-5, A-6, C-1, C 3 and C-5 for an application rate of 320 g / ha showed an efficiency of at least 80% against Stellaria media and Veronica persica.
2. Post-emergence herbicidal action against harmful weed plants
Seeds of monocotyledonous and dicotyledonous herbs and crop plants are placed in wooden fiber pots on sandy soil, covered with soil and grown in a greenhouse with good growing conditions. Two to three weeks after sowing, the test plants are treated in a single leaf stage. The compounds of the invention, formulated in the form of humectable powders (WP) or emulsion concentrates (EC), are then sprayed on the green parts of the plants, in the form of an aqueous suspension or emulsion at a water application rate. 600 to 800 L / ha (converted) with the addition of 0.2% wetting agent. After leaving the test plants to rest in the greenhouse under
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权利要求:
Claims (13)
[1]
1. Compound of N- (1,2,5-oxadiazol-3-yl) -, N- (1,3,4-oxadiazol-2-yl) -, N (tetrazol-5-yl) - or N- (triazol-5-yl) -arylcarboxamides of formula (I), or a salt thereof,
Qx (I), characterized in that the symbol R represents methyl, ethyl, ally, propargyl, CH2OEt, CH2CO2Me or CH2CH2CN;
the symbol W represents N or CY, the symbol X represents methyl, chlorine, SO2Me or SO2Et;
the symbol Z represents CF3 or SO2Me;
the symbol Y represents hydrogen, hydroxyl, SO2Me, SOMe, SMe, chlorine, or
4,5-dihydro-5-acetonitrile-1,2-oxazol) -4-yl;
the symbol V represents hydrogen;
the symbol Q represents a radical Q1, Q3 or Q4, n-n // W
O-N
N — N (Q1) (Q3) (Q4) the R ⁶ symbol represents methyl, propargyl, CO2Me, CO2Et, CO2-i-Pr, CO2CH2CHMe2 or CO2CH2-t-Bu;
R ⁸ represents methyl, ethyl or chlorine;
the symbol R ⁹ represents methyl.
[2]
2. Compound of N- (1,3,4-oxadiazol-3-yl) -, N- (tetrazol-5-yl) -aryl-carboxamide of formula (I), or a salt thereof, according to claim 1, characterized in that the symbol Q represents a radical Q1 or Q4,
N — N

(Q1)
N — N (Q4)
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2/3 and all other radicals and indices each have the meaning as defined in claim 1.
[3]
A compound of N- (tetrazol-5-yl) -arylcarboxamide of formula (I), or a salt thereof, according to claim 1 or 2, characterized in that the symbol Q represents a radical Q1
N — N

(Q1) and all other radicals and indices each have the meaning as defined in claim 1.
[4]
4. Herbicidal composition characterized by having a herbicidal active content of at least one compound of formula (I) as defined in any one of claims 1 to 3.
[5]
5. Herbicidal composition according to claim 4, characterized in that it is in a mixture with formulation aids.
[6]
Herbicidal composition according to claim 4 or 5, characterized in that it comprises at least one other active substance under the pesticide point of view of the group consisting of insecticides, acaricides, herbicides, fungicides, phytoprotective agents and growth regulators.
[7]
Herbicidal composition according to claim 6, characterized in that it comprises a phytoprotective agent.
[8]
Herbicidal composition according to claim 7, characterized in that it comprises cypro-sulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifene-ethyl.
[9]
Herbicidal composition according to any one of claims 6 to 8, characterized in that it comprises another herbicide.
[10]
10. Method for controlling unwanted plants, characterized in that it comprises the application of an effective amount of at least one compound of formula (I), as defined in any one of claims 1 to 3, or of a herbicidal composition, as defined in any one of claims 4 to 9, to plants or to the site of unwanted vegetation.
[11]
Use of a compound of formula (I), as defined in any of claims 1 to 3, or of a herbicidal composition, as defined in
Petition 870190065248, of 7/11/2019, p. 9/10
3/3 any one of claims 4 to 9, characterized in that it is for the control of unwanted plants.
[12]
Use according to claim 11, characterized in that the compounds of formula (I) are used for the control of unwanted plants
5 in useful plant cultures.
[13]
Use according to claim 12, characterized in that the useful plants are transgenic useful plants.

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法律状态:
2018-03-27| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|

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2018-06-26| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2019-01-08| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

---

2019-04-16| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

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2019-09-10| B09A| Decision: intention to grant|

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2019-11-19| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 10/12/2012, OBSERVADAS AS CONDICOES LEGAIS. (CO) 20 (VINTE) ANOS CONTADOS A PARTIR DE 10/12/2012, OBSERVADAS AS CONDICOES LEGAIS |

优先权:

---

申请号 | 申请日 | 专利标题

---

EP11193166|2011-12-13|

---

PCT/EP2012/074975|WO2013087577A1|2011-12-13|2012-12-10|N-, n-, n-, and n- aryl carboxylic acid amides and use thereof as herbicides|

---