2-oxo-3,4-dihydroquinoline compounds as plant growth regulators

Abstract

The present invention relates to novel sulfonamide derivatives of formula (I), to processes and intermediates for preparing them, to plant growth regulator compositions comprising them and to methods of using them for controlling the growth of plants, improving plant tolerance to abiotic stress (including environmental and chemical stresses), inhibiting seed germination and/or safening a plant against phytotoxic effects of chemicals. ##STR00001##

Claims

1. A compound of formula (I) ##STR00046## wherein: R1 is selected from the group consisting of C.sub.1-C.sub.7 alkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.3-C.sub.5 cycloalkyl-C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7alkenyl, C.sub.3-C.sub.7 alkynyl, (3-6 membered heterocycloalkyl)-C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.5 cycloalkyl and a 4-6 membered heterocycloalkyl, each optionally substituted with one to three Rx; R2 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R3, R7 and R8 are independently selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R4 and R5 are independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.3-C.sub.4 cycloalkyl; or R4 and R5 can form, together with the atom or atoms they are directly attached to, a C.sub.3-C.sub.4 cycloalkyl or C.sub.4heterocyclyl; R6 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.3-C.sub.4 alkenyl, C.sub.3-C.sub.4 alkynyl, and C.sub.1-C.sub.3alkoxy-C.sub.1-C.sub.4-alkyl; L is selected from the group consisting of a bond, a linear C.sub.1-C.sub.4-alkyl chain, a linear C.sub.2-C.sub.4-alkenyl chain, a linear C.sub.2-C.sub.4-alkynyl chain, a linear C.sub.1-C.sub.4-alkoxy chain whereby the oxygen atom is attached to A, a linear -amino-C.sub.1-C.sub.4-alkyl-chain whereby the nitrogen atom is attached to A, and a linear C.sub.1-C.sub.2alkyl-oxy-C.sub.1-C.sub.2alkyl, chain each optionally substituted with one to three halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl or C.sub.1-C.sub.4 alkoxy; A is hydrogen, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.5 cycloalkyl, 3-10 membered heterocyclyl or aryl, each optionally substituted with one to three Ry; Rx is, independently of each other, selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4 alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4 aminocarbonyl and C.sub.3-C.sub.4cycloalkyl; Ry is, independently of each other, selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 haloalkyloxy, C.sub.1-C.sub.4alkylsulfanyl, C.sub.1-C.sub.4 haloalkylsulfanyl, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4haloalkylsulfonyl, C.sub.1-C.sub.4 alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4aminocarbonyl and C.sub.3-C.sub.4 cycloalkyl which cycloalkyl is unsubstituted or substituted by one or more Rz; Rz is independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; wherein A is not butyl when either R4 or R5 is methyl; and wherein R1 is not methyl when R2, R3, R4, R5, R6, R7 and R8 are each hydrogen; or salts or N-oxides thereof.

2. The compound of claim 1, wherein R1 is selected from the group consisting of C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.3-C.sub.6 alkenyl and C.sub.3-C.sub.5 cyclopropyl-C.sub.1-C.sub.6-alkyl.

3. The compound of claim 2, wherein R1 is ethyl or propyl.

4. The compound of claim 1, wherein L is a bond.

5. The compound of claim 1, wherein A is selected from the group consisting of C.sub.1-C.sub.7 alkyl, phenyl and 3-6 membered heteroaryl, each optionally substituted with one to three Ry.

6. The compound of claim 5, wherein A is phenyl optionally substituted with one to three substituents independently selected from the group consisting of halogen, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 alkyl and C.sub.1-C.sub.4haloalkoxy.

7. The compound of claim 1, wherein R2 is selected from the group consisting of hydrogen and C.sub.1-C.sub.4 alkyl.

8. The compound of claim 1, wherein R3 is selected from the group consisting of hydrogen, halogen and C.sub.1-C.sub.4 alkyl.

9. The compound of claim 1, wherein R2, R3, R4, R5, R6, R7 and R8 are hydrogen.

10. A composition, comprising: a compound according to claim 1; and an agriculturally acceptable formulation adjuvant.

11. A composition, comprising a compound as defined in claim 1; and an agriculturally active ingredient selected from acaricides, bactericides, fungicides, herbicides, insecticides, nematicides, plant growth regulators, crop enhancing agents, safeners, plant nutrients and plant fertilizers.

12. A method for at least one of improving the tolerance of a plant to abiotic stress, regulating the growth of a plant, or improving the growth of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material, or plant growing locus a compound according to claim 1.

13. A method for inhibiting seed germination of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material or plant growing locus a compound according claim 1.

14. A method for at least one of improving the tolerance of a plant to abiotic stress, regulating the growth of a plant, or improving the growth of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material, or plant growing locus a compound of formula (I) ##STR00047## wherein: R1 is selected from the group consisting of C.sub.1-C.sub.7 alkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.3-C.sub.5 cycloalkyl-C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7alkenyl, C.sub.3-C.sub.7 alkynyl, aryl-C.sub.1-C.sub.7 alkyl, (3-6 membered heterocyclyl)-C.sub.1-C.sub.7 alkyl, phenyl, C.sub.3-C.sub.5 cycloalkyl and a 4-6 membered heterocyclyl, each optionally substituted with one to three Rx; R2 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R3, R7 and R8 are independently selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R4 and R5 are independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.3-C.sub.4 cycloalkyl; or R4 and R5 can form, together with the atom or atoms they are directly attached to, a C.sub.3-C.sub.4 cycloalkyl or C.sub.4heterocyclyl; R6 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.3-C.sub.4 alkenyl, C.sub.3-C.sub.4 alkynyl, and C.sub.1-C.sub.3alkoxy-C.sub.1-C.sub.4-alkyl; L is selected from the group consisting of a bond, a linear C.sub.1-C.sub.4-alkyl chain, a linear C.sub.2-C.sub.4-alkenyl chain, a linear C.sub.2-C.sub.4-alkynyl chain, a linear C.sub.1-C.sub.4-alkoxy chain whereby the oxygen atom is attached to A, a linear -amino-C.sub.1-C.sub.4-alkyl-chain whereby the nitrogen atom is attached to A, and a linear C.sub.1-C.sub.2alkyl-oxy-C.sub.1-C.sub.2alkyl, chain each optionally substituted with one to three halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl or C.sub.1-C.sub.4 alkoxy; A is hydrogen, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.5 cycloalkyl, 3-10 membered heterocyclyl or aryl, each optionally substituted with one to three Ry; Rx is, independently of each other, selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4 alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4 aminocarbonyl and C.sub.3-C.sub.4cycloalkyl; Ry is, independently of each other, selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 haloalkyloxy, C.sub.1-C.sub.4alkylsulfanyl, C.sub.1-C.sub.4 haloalkylsulfanyl, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4haloalkylsulfonyl, C.sub.1-C.sub.4 alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4aminocarbonyl and C.sub.3-C.sub.4 cycloalkyl which cycloalkyl is unsubstituted or substituted by one or more Rz; Rz is independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; wherein A is not butyl when either R4 or R5 is methyl; and wherein R1 is not methyl when R2, R3, R4, R5, R6, R7 and R8 are each hydrogen; or salts or N-oxides thereof.

15. A method for inhibiting seed germination of a plant, wherein the method comprises applying to the plant, plant part, plant propagation material or plant growing locus a compound of formula (I) ##STR00048## wherein: R1 is selected from the group consisting of C.sub.1-C.sub.7 alkyl, C.sub.1-C.sub.7 haloalkyl, C.sub.3-C.sub.5 cycloalkyl C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.7alkenyl, C.sub.3-C.sub.7 alkynyl, aryl-C.sub.1-C.sub.7 alkyl, (3-6 membered heterocyclyl)-C.sub.1-C.sub.7 alkyl, phenyl, C.sub.3-C.sub.5 cycloalkyl and a 4-6 membered heterocyclyl, each optionally substituted with one to three Rx; R2 is selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.4 haloalkyl, C.sub.1-C.sub.4haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R3, R7 and R8 are independently selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4 alkenyl, C.sub.2-C.sub.4 alkynyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 haloalkoxy and C.sub.3-C.sub.4 cycloalkyl; R4 and R5 are independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl and C.sub.3-C.sub.4 cycloalkyl; or R4 and R5 can form, together with the atom or atoms they are directly attached to, a C.sub.3-C.sub.4 cycloalkyl or C.sub.4heterocyclyl; R6 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4 alkyl, C.sub.3-C.sub.4 alkenyl, C.sub.3-C.sub.4 alkynyl, and C.sub.1-C.sub.3alkoxy-C.sub.1-C.sub.4-alkyl; L is selected from the group consisting of a bond, a linear C.sub.1-C.sub.4-alkyl chain, a linear C.sub.2-C.sub.4-alkenyl chain, a linear C.sub.2-C.sub.4-alkynyl chain, a linear C.sub.1-C.sub.4-alkoxy chain whereby the oxygen atom is attached to A, a linear -amino-C.sub.1-C.sub.4-alkyl-chain whereby the nitrogen atom is attached to A, and a linear C.sub.1-C.sub.2alkyl-oxy-C.sub.1-C.sub.2alkyl, chain each optionally substituted with one to three halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl or C.sub.1-C.sub.4 alkoxy; A is hydrogen, C.sub.1-C.sub.7 alkyl, C.sub.3-C.sub.5 cycloalkyl, 3-10 membered heterocyclyl or aryl, each optionally substituted with one to three Ry; Rx is, independently of each other, selected from the group consisting of halogen, cyano, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkoxy, C.sub.1-C.sub.4alkylcarbonyl, C.sub.1-C.sub.4 alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4 aminocarbonyl and C.sub.3-C.sub.4cycloalkyl; Ry is, independently of each other, selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1-C.sub.4 haloalkyl, C.sub.1-C.sub.4 haloalkyloxy, C.sub.1-C.sub.4alkylsulfanyl, C.sub.1-C.sub.4 haloalkylsulfanyl, C.sub.1-C.sub.4 alkylsulfinyl, C.sub.1-C.sub.4 haloalkylsulfinyl, C.sub.1-C.sub.4 alkylsulfonyl, C.sub.1-C.sub.4haloalkylsulfonyl, C.sub.1-C.sub.4 alkylcarbonyl, C.sub.1-C.sub.4alkoxycarbonyl, carboxylic acid, aminocarbonyl, C.sub.1-C.sub.4aminocarbonyl and C.sub.3-C.sub.4 cycloalkyl which cycloalkyl is unsubstituted or substituted by one or more Rz; Rz is independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl; wherein A is not butyl when either R4 or R5 is methyl; and wherein R1 is not methyl when R2, R3, R4, R5, R6, R7 and R8 are each hydrogen; or salts or N-oxides thereof.

Description

PREPARATION EXAMPLES

(1) Schemes 1-7 provide methods of preparing the compounds of formula (I), compounds of formula (II) and compounds of formula (III) of the present invention, wherein R4, R5, R6, R7 and R8 are H when present.

(2) ##STR00033##

(3) Compounds of formula (VII) are commercially available or can be made by methods known to a person skilled in the art. Compounds of formula (VI) may be prepared from a compound of formula (VII) by reaction with an alkylating agent of formula R1-X, wherein X is a leaving group such as halogen, mesylate, triflate or tosylate. For example, R1-X can be propyl iodide, ethyl iodide, allyl bromide or methyl iodide. Such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.

(4) ##STR00034##

(5) Compounds of formula (VIIa) are commercially available or can be made by methods known to a person skilled in the art. Compounds of formula (VIa) may be prepared from a compound of formula (VIIa) by reaction with an alkylating agent of formula R1-X, wherein X is a leaving group such as halogen, mesylate, triflate or tosylate. For example, R1-X can be propyl iodide, ethyl iodide, allyl bromide or methyl iodide. Such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.

(6) ##STR00035##

(7) Compounds of formula (V), wherein R4, R5 and R6 are H, may be prepared from a compound of formula (VI) by reaction with 2-chloro-N-(hydroxymethyl)acetamide in a solvent such as acetic acid, and optionally in the presence of stronger acid such as sulfuric acid, followed by hydrolysis of the resulting 2-chloroacetamide with an acid such as HCl in an alcoholic solvent. Compound (V) can be obtained as its hydrochloride salt or a free amine after neutralization with a base.

(8) ##STR00036##

(9) Compounds of formula (V), wherein R4 and R5 are H, may be prepared from a compound of formula (VIb) wherein X is a leaving group such as halogen, by reaction with an amine of formula R6NH.sub.2 or its hydrochloride salt of formula R6NH.sub.3Cl, in the presence or not of a base such as triethyl amine or diisopropylamine. For example, R6NH.sub.2 can be ammonia, methyl amine or ethyl amine.

(10) The compound of formula (VIb) may be obtained from a compound of formula (VIa) wherein X is a leaving group such as Cl or Br, by radical reaction with N-bromosuccinimide or N-chlorosuccinimide in the presence of an initiator such as AIBN or dibenzoyl peroxide.

(11) ##STR00037##

(12) Compounds of formula (V), wherein R4, R5 and R6 are H, may be prepared from a compound of formula (VIII) by reduction of the cyano moiety under hydrogen atmosphere in the presence of a catalyst such as palladium on charcoal, or by reducing agent such as sodium borohydride in the presence of a catalyst such as nickel chloride or cobalt chloride for example.

(13) The compound of formula (VIII) may be obtained from a compound of formula (IX) wherein X is a leaving group such as Cl or Br, I or OTf by a coupling reaction with a cyanide salt such as CuCN, NaCN, K.sub.3[Fe(CN).sub.6], in the presence or not of a catalyst such as palladium (0) or cupper, eventually with an additional ligant as described in the literature (see Zanon et al, J. Am. Chem Soc. 2003, 125, 2890-2891, Buchwald, S & all, Angew. Chem. Int. Ed. 2013, 52: 10035-10039).

(14) The compound of formula (IX) may be obtained from a compound of formula (IXa) by reaction with an alkylating agent of formula R1-X, wherein X is a leaving group such as halogen, mesylate, triflate or tosylate. For example, R1-X can be propyl iodide, ethyl iodide, allyl bromide, or methyl iodide. Such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.

(15) Alternatively, compound of formula (VIII) may be obtained from a compound of formula (VIIIa) by reaction with an alkylating agent of formula R1-X, wherein X is a leaving group such as halogen, mesylate, triflate or tosylate. For example, R1-X can be propyl iodide, ethyl iodide, allyl bromide, or methyl iodide. Such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.

(16) Compound of formula (VIIIa) may be prepared from compound (IXa) wherein X is a leaving group such as Cl or Br, I or OTf by a coupling reaction with a cyanide salt as described for compound (VIIIa)

(17) ##STR00038##

(18) Compounds of formula (V) wherein R5 is H, may be prepared from a compound of formula (X) by amino reduction of the carbonyl moiety in the presence of an amine of formula R6NH.sub.2 or its corresponding salt in the presence of a reducing agent such as sodium cyanoborohydride and eventually of an additional organic acid such as acetic acid.

(19) The compound of formula (X) may be obtained from a compound of formula (Xa) by reaction with an alkylating agent of formula R1-X, wherein X is a leaving group such as halogen, mesylate, triflate or tosylate. For example, R1-X can be propyl iodide, ethyl iodide, allyl bromide, or methyl iodide. Such reactions are usually carried out in the presence of a base, and optionally in the presence of a nucleophilic catalyst.

(20) ##STR00039##

(21) Compounds of formula (I) may be prepared from a compound of formula (V) by reaction with sulfonyl chloride of formula A-L-SO.sub.2Cl. Such reactions are usually carried out in the presence of an organic base, such as N-ethyldiisopropylamine. For example, A-L-SO.sub.2Cl can be benzenesulfonyl chloride, benzylsulfonyl chloride or butylsulfonyl chloride. Compounds of formula A-L-SO.sub.2Cl are commercially available or can be made by methods known to a person skilled in the art.

Example P1: Preparation of 2,4-dimethyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]benzenesulfonamide (Compound 3.014)

(22) ##STR00040##

a. 1-propyl-3,4-dihydroquinolin-2-one

(23) 3,4-Dihydro-1H-quinolin-2-one (5.00 g, 34 mmol) was dissolved in dimethylformamide (DMF) (49 mL). Potassium carbonate (14.2 g, 102 mmol) was added. At room temperature, 1-bromopropane (12.5 g, 102 mmol, 9.27 mL) was added dropwise. The reaction mixture was stirred four days at room temperature and then heated for 4 h at 60 C. The reaction mixture was cooled to room temperature and poured into 200 mL of ice-water. The water-phase was extracted with 100 ml ethyl acetate (EtOAc). The combined organic phases were washed with water and brine. The organic phase was dried with Na.sub.2SO.sub.4, filtrated and concentrated to give 7.3 g of pale yellow oil. The crude product was purified on silica gel to give 1-propyl-3,4-dihydroquinolin-2-one (5.2 g, 27.5 mmol, 81%) as a colorless oil. .sup.1H NMR (CDCl.sub.3, 400 MHz) 0.96 (3H, t); 1.68 (2H, sxt); 2.64 (2H, m); 2.88 (2H, m); 3.90 (2H, t); 6.99 (2H, m); 7.16 (1H, m); 7.24 (1H, m).

b. 6-(aminomethyl)-1-propyl-3,4-dihydroquinolin-2-one

(24) 1-Propyl-3,4-dihydroquinolin-2-one (4.50 g, 23.8 mmol) was added to a solution of acetic acid (234 mL) and sulfuric acid (2.4 mL). At room temperature, 2-chloro-N-(hydroxymethyl)acetamide (3.53 g, 28.5 mmol) was added. The reaction mixture was stirred for 72 h. The reaction mixture was poured into ice, and the mixture was extracted with tert-butyl methyl ether. The combined organic phases were washed with brine. The organic phase was dried with Na.sub.2SO.sub.4, filtrated and concentrated. 7.8 g of crude amide was obtained and purified on silica gel to give 4.1 g of the corresponding 2-chloroacetamide, which was further stirred in petrol ether, filtrated and dried to give 3.4 g of a white solid.

(25) The resulting 2-chloroacetamide was dissolved into a 1:1 mixture of HCl conc./EtOH (25 mL), and then heated to reflux for 3 h, followed by stirring overnight. The reaction mixture was heated again for 2 h at reflux. The solvent was evaporated under reduced pressure and the residue was stirred in ether, filtrated and dried to give 6-(aminomethyl)-1-propyl-3,4-dihydroquinolin-2-one hydrochloride (3.26 g, 12.8 mmol, 54% yield) as a beige solid. .sup.1H NMR (DMSO, 400 MHz) 0.87 (3H, t); 1.51 (2H, sxt); 2.53 (2H, m); 2.85 (2H, t); 3.87 (2H, t); 3.94 (2H, q); 4.86 (2H, br s); 7.18 (1H, d); 7.37 (1H, s); 7.41 (1H, d).

c. 2,4-dimethyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]benzenesulfonamide (Compound 3.014)

(26) 6-(aminomethyl)-1-propyl-3,4-dihydroquinolin-2-one (0.055 g, 0.216 mmol) was stirred in EtOAc (4 mL). The reaction mixture was cooled on ice. Diisopropylethylamine (0.132 mL, 0.756 mmol) was added and then 2,4-dimethylbenzenesulfonyl chloride (0.059 g, 0.281 mmol). The reaction mixture was stirred 3 h at 50 C. The reaction mixture was concentrated. The crude product was purified on silica gel to give 2,4-dimethyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]benzenesulfonamide (59.4 mg, 0.154 mmol, 71% yield) as a white solid. Mp.: 166-167 C.; .sup.1H NMR (CDCl.sub.3, 400 MHz) 0.94 (3H, t); 1.62 (2H, sxt); 2.37 (3H, s); 2.58 (4H, m); 2.78 (2H, m); 3.85 (2H, t); 4.05 (2H, d, J=6.2); 4.89 (1H, t); 6.86 (1H, d); 6.95 (1H, s); 7.04 (1H, dd); 7.10 (2H, m).

Example P2: Preparation of N-[(2-oxo-1-propyl-6-quinolyl)methyl]benzenesulfonamide (Compound 7.001)

(27) ##STR00041##

a. 6-methyl-1-propyl-quinolin-2-one

(28) 6-Methyl-1H-quinolin-2-one (5.00 g, 31.41 mmol) was dissolved in DMF (50 mL). Potassium carbonate (8.68 g, 62.8 mmol) was added, followed by 1-bromopropane (19.3 g, 157 mmol, 14.3 mL). The reaction mixture was stirred overnight at room temperature and then poured into 200 mL of ice-water. The water-phase was extracted with ethyl acetate and the combined organic phases were washed with water and brine. The organic phase was dried with Na.sub.2SO.sub.4, filtrated and concentrated to give 9.1 g of pale yellow oil. The crude product was purified on silica gel to give 6-methyl-1-propyl-quinolin-2-one (2.3 g, 11 mmol, 36%) as a colorless oil. .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.04 (t, 3H), 1.73-1.82 (m, 2H), 2.41 (s, 3H), 4.20-4.27 (m, 2H), 6.65-6.70 (m, 1H), 7.26 (s, 1H), 7.33-7.39 (m, 2H), 7.60 (d, 1H); LC-MS (Method A): RT 0.90, (202, M+H.sup.+).

b. 6-(bromomethyl)-1-propyl-quinolin-2-one

(29) 6-Methyl-1-propyl-quinolin-2-one (2.5 g, 12 mmol) was solved in a solution of carbon tetrachloride (5 mL) and 1-bromopyrrolidine-2,5-dione (2.5 g, 14 mmol). The reaction mixture was stirred and heated at 80 C. then azobisisobutyronitrile (0.2 g, 1.2 mmol) was added. The resulting was stirred at 80 C. for 6 h and cooled. Water was added and the mixture was extracted with ethyl acetate. The combined organic phases were washed with brine, dried with Na.sub.2SO.sub.4, filtrated and concentrated to give 0.61 g of brown oil. The crude product was purified on silica gel to give 6-(bromomethyl)-1-propyl-quinolin-2-one (2.6 g, 9.3 mmol, 75%). .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 1.02-1.08 (m, 3H), 1.77 (sxt, 2H), 4.19-4.29 (m, 2H), 4.58 (s, 2H), 6.72 (d, 1H), 7.31-7.36 (m, 1H), 7.56-7.66 (m, 3H); LC-MS (Method A): RT 0.94, (280, M+H.sup.+).

c. 6-(aminomethyl)-1-propyl-quinolin-2-one

(30) 6-(Bromomethyl)-1-propyl-quinolin-2-one (1.6 g, 5.7 mmol) was dissolved in a solution of NH.sub.3/MeOH (41 mL, 7 mol/L). The yellow solution was stirred for overnight, after complete conversion the solution was concentrated on vacuum and purified on silica gel to give 6-(aminomethyl)-1-propyl-quinolin-2-one (710 mg, 3.28 mmol, 57%); .sup.1H NMR (400 MHz, MeOH) ppm 1.03 (t, 3H), 1.72-1.81 (m, 2H), 4.20 (s, 2H), 4.29-4.35 (m, 2H), 6.72 (d, 1H), 7.66-7.74 (m, 2H), 7.78 (d, 1H), 7.92 (d, 1H); LC-MS (Method A): RT 0.26, (218, M+H.sup.+).

d. N-[(2-oxo-1-propyl-6-quinolyl)methyl]benzenesulfonamide (Compound 7.001)

(31) 6-(Aminomethyl)-1-propyl-quinolin-2-one (0.100 g, 0.462 mmol) was stirred in EtOAc (4 mL). The reaction mixture was cooled on ice. Diisopropylethylamine (0.179 mg, 1.38 mmol) was added and then benzenesulfonyl chloride (0.089 g, 0.508 mmol). The reaction mixture was stirred 1 h and concentrated. The crude product was purified on silica gel to give N-[(2-oxo-1-propyl-6-quinolyl)methyl]benzenesulfonamide (86 mg, 52% yield) as a white solid. Mp.: 204-206 C.; 1H NMR (400 MHz, DMSO-d6) ppm 0.93 (t, 3H), 1.60 (sxt, 2H), 4.06 (d, 2H), 4.11-4.21 (m, 2H), 6.53-6.64 (m, 1H), 7.51 (s, 1H), 7.41-7.48 (m, 2H), 7.51-7.64 (m, 3H), 7.76-7.86 (m, 3H), 8.21 (t, 1H); LC-MS (Method A): RT 0.85, (357, M+H.sup.+).

Example P3: Preparation of N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)ethyl]benzenesulfonamide (Compound 14.001)

(32) ##STR00042##

a. Preparation of 6-acetyl-1-propyl-3,4-dihydroquinolin-2-one

(33) 6-Acetyl-3,4-dihydro-1H-quinolin-2-one (500 mg, 2.64 mmol) was dissolved in DMF (5 mL) and potassium carbonate (0.547 g, 3.96 mmol) was added followed by 1-bromopropane (0.487 g, 3.96 mmol, 0.36 mL). The reaction mixture was stirred overnight at room temperature and more potassium carbonate (0.550 g, 1.5 eq.) and 1-bromopropane (0.18 mL, 0.75 eq.) were added. The reaction mixture was heated at 50 C. until to have a complete conversion, cooled to room temperature and poured into ice-water. The water-phase was extracted with ethyl acetate. The combined organic phases were washed with water and brine, dried with Na.sub.2SO.sub.4, filtrated and concentrated. The crude product was purified on silica gel to give 6-acetyl-1-propyl-3,4-dihydroquinolin-2-one (499 mg, 2.15 mmol, 81%) as a white solid. Mp.: 90-93 C.; .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 0.97 (t, 3H), 1.62-1.72 (m, 2H), 2.57-2.59 (m, 3H), 2.68 (dd, 2H), 2.93-2.98 (m, 2H), 3.89-3.97 (m, 2H), 7.03 (d, 1H), 7.77-7.88 (m, 2H); LC-MS (Method A): RT 0.84, (232, M+H.sup.+).

b. Preparation of 6-(1-aminoethyl)-1-propyl-3,4-dihydroquinolin-2-one

(34) 6-Acetyl-1-propyl-3,4-dihydroquinolin-2-one (480 mg, 2.08 mmol) was dissolved in methanol (7 mL, 2.08 mmol) then ammonium acetate (1.62 g, 20.8 mmol) and sodium cyanoborohydride (0.686 g, 10.4 mmol) were added. The reaction mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure and the residue was dissolved in ethyl acetate and acidified with 2M HCl (until pH: 2). The organic layer was discarded. Then, the aqueous layer was treated with 2M NaOH (until pH: 12) and extracted 3 with ethyl acetate. The combined org layer was washed with brine, dried over Na.sub.2SO.sub.4, filtrated and evaporated to give 177 mg of uncolored oil. .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 0.96 (t, 3H), 1.38 (d, 3H), 1.66-1.72 (m, 2H), 2.63 (dd, 2H), 2.84-2.91 (m, 2H), 3.85-3.91 (m, 2H), 4.06-4.16 (m, 2H), 6.94 (d, 1H), 7.15-7.22 (m, 2H); LC-MS (Method A): RT 0.76, (234, M+H.sup.+).

c. N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)ethyl]benzenesulfonamide (Compound 14.001)

(35) 6-(1-Aminoethyl)-1-propyl-3,4-dihydroquinolin-2-one (0.050 g, 0.215 mmol) was stirred in EtOAc (2 mL). The reaction mixture was cooled on ice. Diisopropylethylamine (0.093 mL, 0.538 mmol) was added and then benzenesulfonyl chloride (0.039 g, 0.215 mmol). The reaction mixture was stirred overnight and concentrated. The crude product was purified on silica gel to give N-[(2-oxo-1-propyl-6-quinolyl)methyl]benzenesulfonamide (49 mg, 61% yield) as a colourless gum. .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 0.94 (t, 3H), 1.42 (d, 3H), 1.62 (sxt, 2H), 2.49-2.59 (m, 2H), 2.64-2.81 (m, 2H), 3.77-3.89 (m, 2H), 4.47 (quin, 1H), 5.08-5.26 (m, 1H), 6.79 (d, 1H), 6.84 (d, 1H), 6.99 (dd, 1H), 7.33-7.42 (m, 2H), 7.44-7.52 (m, 1H), 7.67-7.80 (m, 2H); LC-MS (Method A): RT 0.93, (373, M+H.sup.+).

Example P4: Preparation of N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)cyclopropyl]benzenesulfonamide (Compound 15.001)

(36) ##STR00043##

a. Preparation of 6-(1-aminocyclopropyl)-1-propyl-3,4-dihydroquinolin-2-one

(37) Under argon, 2-oxo-1-propyl-3,4-dihydroquinoline-6-carbonitrile (0.215 g, 1 mmol) was dissolved in diethyl ether (10 ml). Titanium(IV) isopropoxide (0.323 g, 1.1 mmol) was added and reaction mixture was cooled to 0 C. Ethylmagnesium bromide (1.0 mol/L) in TBME (2.2 mL, 1.9 g, 2.2 mmol) was added dropwise and stirred for 10 min then warmed up to room temperature. Bortrifluoriddiethyletherat (0.265 ml, 0.323 g) was added and stirred. A solution of hydrochloride acid (1M) was added, then TBME at the reaction mixture, aqueous layer was collected and treated with sodium hydroxide (2M) until pH=10). Then it was extracted with TBME three times. Organic layer were combined, washed with brine, dried on Na.sub.2SO.sub.4 and concentrated on vacuum. The residue was purified with silica gel to give 6-(1-aminocyclopropyl)-1-propyl-3,4-dihydroquinolin-2-one (77 mg, 0.315 mmol) as a colourless oil. .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 0.94 (d, 3H) 1.66 (sxt, 2H) 2.61-2.66 (m, 2H) 2.85-2.90 (m, 2H) 3.85-3.91 (m, 2H) 6.92 (d, 1H) 7.09-7.19 (m, 2H). LC-MS (Method A): RT 0.55, (245, M+H.sup.+).

b. N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)cyclopropyl]benzenesulfonamide (Compound 15.001)

(38) 6-(1-Aminocyclopropyl)-1-propyl-3,4-dihydroquinolin-2-one (0.050 g, 0.204 mmol) was stirred in EtOAc (2 mL). The reaction mixture was cooled on ice. Diisopropylethylamine (0.087 mL, 0.511 mmol) was added and then benzenesulfonyl chloride (0.037 g, 0.204 mmol). The reaction mixture was stirred overnight and concentrated. The crude product was purified on silica gel to give N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)cyclopropyl]benzenesulfonamide (57 mg, 72% yield) as a colourless gum. .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 0.87-0.98 (m, 3H), 1.02-1.08 (m, 2H), 1.29-1.37 (m, 2H), 1.59 (sxt, 2H), 2.48-2.57 (m, 2H), 2.61-2.70 (m, 2H), 3.76-3.88 (m, 2H), 6.11 (s, 1H), 6.64-6.74 (m, 1H), 6.84 (d, 1H), 7.01 (dd, 1H), 7.24-7.32 (m, 2H), 7.36-7.44 (m, 1H), 7.61-7.68 (m, 2H); LC-MS (Method A): RT 0.93, (385, M+H.sup.+).

Example P5: Preparation of 6-(aminomethyl)-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-2-one (Compound 11.001)

(39) ##STR00044##

a. 2-oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinoline-6-carbonitrile

(40) 2-Oxo-3,4-dihydroquinoline-6-carbonitrile (0.500 g, 2.90 mmol) was dissolved in DMF (15 mL) and potassium carbonate (1.01 g, 7.26 mmol) was added followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.604 mL, 4.07 mmol) dropwise. The reaction mixture was heated to 50 C. and stirred for 2 h. An other 0.5 equivalent of 2,2,2-trifluoroethyl trifluoromethanesulfonate (0.216 mL) was added and the reaction mixture was stirred for another 2 h. The reaction mixture was poured on water and it was extracted with ethyl acetate. The combined organic layers were washed with water and with brine, dried over Na.sub.2SO.sub.4 and concentrated. The crude product was purified on silica gel to give 2-oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinoline-6-carbonitrile (0.485 g, 66%) as a pale yellow gum; .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 2.73-2.81 (m, 2H), 2.98-3.07 (m, 2H), 4.67 (q, 2H), 7.15 (d, 1H), 7.45-7.53 (m, 1H), 7.59 (dd, 1H); LC-MS (Method A): RT 0.84, (255, M+H.sup.+).

b. 6-(aminomethyl)-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-2-one

(41) 2-Oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinoline-6-carbonitrile (0.485 g, 1.91 mmol) and Pd/C 10% (0.049 g, 0.046 mmol) were put in a flask under argon and degassed ethanol (19 mL) was added. Aqueous hydrochloric acid (32 mass %, 1.404 mL) was added and the reaction mixture was stirred under an atmosphere of molecular hydrogen overnight. The reaction mixture was filtered trough a pad of celite and concentrated to give the crude 6-(aminomethyl)-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-2-one (602 mg, quant) as its hydrochloride salt. The compound was used as such for the next step. .sup.1H NMR (400 MHz, METHANOL-d4) ppm 2.70 (t, 2H), 2.98 (t, 2H), 4.08 (s, 2H), 4.74-4.85 (m, 2H), 7.26-7.47 (m, 3H); LC-MS (Method A): RT 0.30, (255, M+H.sup.+).

c. N-[[2-oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide (Compound 11.001)

(42) 6-(Aminomethyl)-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-2-one hydrochloride (0.150 g, 0.509 mmol) was suspend in ethyl acetate (5 mL) and N-ethyl-N-isopropyl-propan-2-amine (0.218 mL, 1.27 mmol) was added dropwise. Then benzenesulfonyl chloride (0.102 g, 0.560 mmol) was added dropwise and the reaction mixture was stirred for 3 h at room temperature. The solvent were removed under vacuum and the crude compound was purified on silica gel to give N-[2-oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide (144 mg, 71%) of a pale yellow solid. .sup.1H NMR (400 MHz, CHLOROFORM-d) ppm 1.26 (t, 1H), 2.05 (s, 1H), 2.61-2.72 (m, 2H), 2.82-2.91 (m, 2H), 4.04-4.17 (m, 2H), 4.04-4.19 (m, 3H), 4.61 (q, 2H), 5.03 (t, 1H), 6.94 (d, 1H), 7.01-7.06 (m, 1H), 7.07-7.16 (m, 1H), 7.47-7.54 (m, 2H), 7.55-7.66 (m, 1H), 7.86 (d, 2H); LC-MS (Method A): RT 0.92, (399, M+H.sup.+).

Example P6: Preparation of N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide 9.001

(43) ##STR00045##

a. 1-(3-pyridyl)-3,4-dihydroquinolin-2-one

(44) Under Argon, 3,4-dihydro-1H-quinolin-2-one (0.736 g, 5.00 mmol), cesium carbonate (4.14 g, 12.5 mmol), copper Iodide (0.145, 1 mmol) and ethyl 2-oxocyclohexanecarboxylate (0,426 g, 2.25 mmol) were added. Then 3-iodopyridine (1.13 g, 5.5 mmol) in dimethylsulfoxide (5 mL) was added, and the reaction mixture was heated at 110 C. for 3 h. The mixture was poured into 20 mL of ice-water, the water-phase was extracted with ethyl acetate and the combined organic phases were washed with water and brine, dried with Na.sub.2SO.sub.4, filtrated and concentrated. The crude product was purified on silica gel to give 1-(3-pyridyl)-3,4-dihydroquinolin-2-one (746 mg, 3.32 mmol, 66.5%). .sup.1H NMR (400 MHz, CDCl.sub.3) ppm 2.82-2.89 (m, 2H), 3.06-3.13 (m, 2H), 6.34 (d, 1H), 7.00-7.10 (m, 2H), 7.24 (d, 1H), 7.46 (dd, 1H), 7.64 (dt, 1H), 8.52 (d, 1H), 8.66 (dd, 1H); LC-MS (Method A): RT 0.72, (225, M+H.sup.+).

b. 6-(aminomethyl)-1-(3-pyridyl)-3,4-dihydroquinolin-2-one

(45) 1-(3-Pyridyl)-3,4-dihydroquinolin-2-one (312 mg, 1.39 mmol) in acetic acid (5 mL) was dissolved in sulfuric acid (1.5 mL), then 2chloro-N-(hydroxymethyl)acetamide (0.171 g, 1.39 mmol) was added, reaction mixture was stirred at room temperature for 2 hours at 50 C. Ice water and a solution of potassium carbonate were added, the water phase was extracted with ethyl acetate, and the organic phase was dried and concentrated on vacuum. The crude product was purified by flash chromatography to give 2-chloro-N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6-yl]methyl]acetamide (177 mg, 38%); H NMR (400 MHz, CDCl.sub.3) ppm 2.84 (dd, 2H), 3.05-3.13 (m, 2H), 4.06-4.13 (m, 2H), 4.43 (d, 2H), 6.32 (d, 1H), 6.90 (br. s., 1H), 6.99 (d, 1H), 7.19 (s, 1H), 7.47 (dd, 1H), 7.62 (dt, 1H), 8.50 (d, 1H), 8.67 (dd, 1H); LC-MS (Method A): RT 0.62, (328, MH.sup.+), (329, M+H.sup.+).

(46) 2-Chloro-N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6-yl]methyl]acetamide (167 mg, 0.506 mmol) in ethanol (1.25 mL) was added hydrochloride acid (1.25 mL). Reaction mixture was stirred over night at 90-95 C. Ethanol (10 mL) was added at this mixture and the precipitate was filtered then washed with ethyl ether to give 6-(aminomethyl)-1-(3-pyridyl)-3,4-dihydroquinolin-2-one dihydrochloride (155 mg, 93%) which was used directly for the next step; LC-MS (Method A): RT 0.22, (254, M+H.sup.+).

c. Preparation of N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide (Compound 9.001)

(47) 6-(Aminomethyl)-1-(3-pyridyl)-3,4-dihydroquinolin-2-one dihydrochloride (0.163 g, 0.50 mmol) was suspend in ethyl acetate (6.5 mL) with diisopropylethylamine (0.226 g, 1.75 mmol) and stirred at room temperature during 15 min. Benzenesulfonyl chloride (0.115 g, 0.65 mmol) was added and reaction mixture was stirred over the weekend at room temperature. Water was added and extracted two times with ethyl acetate. The combined organic phases were washed with a solution of sodium hydrogen carbonate, dried and concentrated to give N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide (48 mg, 24%) after a purification by flash chromatography. H NMR (400 MHz, CDCl.sub.3) ppm 2.76-2.85 (m, 2H), 2.98-3.05 (m, 2H), 4.06-4.13 (m, 2H), 4.83 (t, 1H), 6.23 (d, 1H), 6.88 (d, 1H), 7.11 (s, 1H), 7.46 (dd, 1H), 7.49-7.56 (m, 2H), 7.60 (d, 2H), 7.87 (d, 2H), 8.42 (d, 1H), 8.66 (d, J=3.67 Hz, 1H); LC-MS (Method A): RT 0.79, (392, MH.sup.+), (394, M+H.sup.+).

(48) Compounds of the present invention were made using these methods, as shown in the table below.

(49) TABLE-US-00002 RT [M + H] MP Compound Name (min) (measured) Method ( C.) 2.024 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-(p- 0.91 373 A tolyl)methanesulfonamide 3.024 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 0.96 387 A (p-tolyl)methanesulfonamide 2.015 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-4- 0.94 413 A 180-181 (trifluoromethyl)benzenesulfonamide 2.012 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-4- 0.89 359 A 202-203 methyl-benzenesulfonamide 3.012 4-methyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.94 373 A 153-154 yl)methyl]benzenesulfonamide 3.015 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-4- 0.99 427 A 138-140 (trifluoromethyl)benzenesulfonamide 2.006 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2,4- 0.86 381 A 167-168 difluoro-benzenesulfonamide 2.009 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-4- 0.85 363 A 190-191 fluoro-benzenesulfonamide 2.017 2-bromo-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.87 425 A 206-207 yl)methyl]benzenesulfonamide 2.011 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 0.88 359 A 203-206 methyl-benzenesulfonamide 2.014 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2,4- 0.93 373 A 199-200 dimethyl-benzenesulfonamide 2.001 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.84 346 A 114-124 yl)methyl]benzenesulfonamide 2.010 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-4- 0.85 375 A 147-150 methoxy-benzenesulfonamide 2.007 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 0.84 364 A 155-163 fluoro-benzenesulfonamide 2.002 4-bromo-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 176-183 yl)methyl]benzenesulfonamide 3.006 2,4-difluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.91 395 A 141-144 yl)methyl]benzenesulfonamide 3.005 2,6-difluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.88 395 A 182-183 yl)methyl]benzenesulfonamide 3.009 4-fluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.9 377 A 143-144 yl)methyl]benzenesulfonamide 3.007 2-fluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.89 377 A 155-156 yl)methyl]benzenesulfonamide 3.001 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.89 359 A 159-161 yl)methyl]benzenesulfonamide 3.011 2-methyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 373 A 163-165 yl)methyl]benzenesulfonamide 3.004 4-chloro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.95 393 A 138-139 yl)methyl]benzenesulfonamide 3.010 4-methoxy-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.9 390 A 143-144 yl)methyl]benzenesulfonamide 3.014 2,4-dimethyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.98 388 A 166-167 yl)methyl]benzenesulfonamide 3.017 2-bromo-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 439 A 157-159 yl)methyl]benzenesulfonamide 3.016 4-isopropoxy-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.99 417 A 138-139 yl)methyl]benzenesulfonamide 3.002 4-bromo-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.96 439 A 143-145 yl)methyl]benzenesulfonamide 3.023 1-(2-fluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.41 391 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.025 1-(2,4-difluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.44 409 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.026 1-(2,6-difluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.42 409 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.036 1-(4-bromo-2-fluoro-phenyl)-N-[(2-oxo-1-propyl-3,4- 1.58 469 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.037 1-(2,5-difluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.43 409 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.038 1-(2,3-difluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.44 409 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.039 1-(2-bromo-4-fluoro-phenyl)-N-[(2-oxo-1-propyl-3,4- 1.55 469 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.040 1-(2-bromo-4-chloro-phenyl)-N-[(2-oxo-1-propyl-3,4- 1.66 485 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.041 1-(4-cyanophenyl)-N-[(2-oxo-1-propyl-3,4- 1.3 398 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.042 1-(4-cyano-2-fluoro-phenyl)-N-[(2-oxo-1-propyl-3,4- 1.35 416 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.043 1-(2-cyanophenyl)-N-[(2-oxo-1-propyl-3,4- 1.31 398 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.044 1-(2-chloro-4-fluoro-phenyl)-N-[(2-oxo-1-propyl-3,4- 1.49 425 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.045 1-(4-tert-butylphenyl)-N-[(2-oxo-1-propyl-3,4- 1.77 429 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.046 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.62 457 B [4-(trifluoromethoxy)phenyl]methanesulfonamide 3047 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.58 441 B [4-(trifluoromethyl)phenyl]methanesulfonamide 3.033 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.57 441 B [3-(trifluoromethyl)phenyl]methanesulfonamide 3.031 1-(4-chlorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.51 407 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.050 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.7 473 B [4-(trifluoromethylsulfanyl)phenyl]methanesulfonamide 3.032 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.4 442 B [6-(trifluoromethyl)-3-pyridyl]methanesulfonamide 3.022 1-(2-bromophenyl)-N-[(2-oxo-1-propyl-3,4- 1.52 451 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.035 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-2- 1.45 387 B phenyl-ethanesulfonamide 3.030 1-(3-fluorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.41 391 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.029 1-(2,4-dichlorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.64 441 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.049 1-(3-bromophenyl)-N-[(2-oxo-1-propyl-3,4- 1.53 451 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.028 1-(4-nitrophenyl)-N-[(2-oxo-1-propyl-3,4- 1.38 418 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.022 1-(4-bromophenyl)-N-[(2-oxo-1-propyl-3,4- 1.54 451 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.034 methyl 3-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 1.13 369 B yl)methylsulfamoyl]propanoate 3.021 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]-1- 1.38 373 B phenyl-methanesulfonamide 3.019 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 1.34 339 B yl)methyl]butane-1-sulfonamide 3.018 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 1.15 323 B yl)methyl]cyclopropanesulfonamide 2.023 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-(2- 1.29 377 B fluorophenyl)methanesulfonamide 2.025 1-(2,4-difluorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.33 395 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.026 1-(2,6-difluorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.31 395 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.036 1-(4-bromo-2-fluoro-phenyl)-N-[(1-ethyl-2-oxo-3,4- 1.47 455 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.037 1-(2,5-difluorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.32 395 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.038 1-(2,3-difluorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.33 395 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.039 1-(2-bromo-4-fluoro-phenyl)-N-[(1-ethyl-2-oxo-3,4- 1.57 455 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.040 1-(2-bromo-4-chloro-phenyl)-N-[(1-ethyl-2-oxo-3,4- 1.56 471 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.041 1-(2-cyanophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.2 384 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.042 1-(2-chloro-4-fluoro-phenyl)-N-[(1-ethyl-2-oxo-3,4- 1.39 411 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.045 1-(4-tert-butylphenyl)-N-[(1-ethyl-2-oxo-3,4- 1.68 415 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.046 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-[4- 1.53 443 B (trifluoromethoxy)phenyl]methanesulfonamide 2.047 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-[4- 1.49 427 B (trifluoromethyl)phenyl]methanesulfonamide 2.033 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-[3- 1.48 427 B (trifluoromethyl)phenyl]methanesulfonamide 2.031 1-(4-chlorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.41 393 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.032 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-[6- 1.29 428 B (trifluoromethyl)-3-pyridyl]methanesulfonamide 2.048 1-(2-bromophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.41 437 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.035 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 1.34 373 B phenyl-ethanesulfonamide 2.030 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1-(3- 1.3 377 B fluorophenyl)methanesulfonamide 2.029 1-(2,4-dichlorophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.54 427 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.049 1-(3-bromophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.43 437 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.022 1-(4-bromophenyl)-N-[(1-ethyl-2-oxo-3,4- 1.44 437 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.034 methyl 3-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 1.01 355 B yl)methylsulfamoyl]propanoate 2.021 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1- 1.27 359 B phenyl-methanesulfonamide 2.019 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 1.22 325 B yl)methyl]butane-1-sulfonamide 3.027 1-(4-cyclopropylphenyl)-N-[(2-oxo-1-propyl-3,4- 1.7 413 B dihydroquinolin-6-yl)methyl]methanesulfonamide 2.027 1-(4-cyclopropylphenyl)-N-[(1-ethyl-2-oxo-3,4- 1.6 399 B dihydroquinolin-6-yl)methyl]methanesulfonamide 3.051 (E)-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]- 0.94 385 A 165-168 2-phenyl-ethenesulfonamide 3.053 (E)-2-(4-chlorophenyl)-N-[(2-oxo-1-propyl-3,4- 1.00 419 A 153-154 dihydroquinolin-6-yl)methyl]methenesulfonamide 3.056 (E)-2-(2-fluorophenyl)-N-[(2-oxo-1-propyl-3,4- 0.95 403 A 139-173 dihydroquinolin-6-yl)methyl]ethenesulfonamide 2.051 (E)-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 0.88 371 A 134-137 phenyl-ethenesulfonamide 3.060 (E)-N-[(2-oxo-1-propyl-6-quinolyl)methyl]prop-1-ene-1- 0.83 323 A 95-99 sulfonamide 3.020 4,4,4-trifluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.90 393 A yl)methyl]butane-1-sulfonamide 3.061 5-methyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.95 379 A 151-154 yl)methyl]thiophene-2-sulfonamide 2.059 (E)-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 0.93 385 A 151-153 (p-tolyl)ethenesulfonamide 2.062 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.8 311 A yl)methyl]propane-1-sulfonamide 3.063 1-methyl-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.73 363 A 168-171 yl)methyl]imidazole-4-sulfonamide 2.063 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-1- 0.63 349 A 165-167 methyl-imidazole-4-sulfonamide 2.064 2,5-dichloro-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.94 421 A 198-201 yl)methyl]thiophene-3-sulfonamide 2.018 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.75 309 A 104-106 yl)methyl]cyclopropanesulfonamide 3.059 (E)-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]- 0.97 399 A 172-174 2-(p-tolyl)ethenesulfonamide 3.052 (E)-2-(4-bromophenyl)-N-[(2-oxo-1-propyl-3,4- 1.01 465 A 150-152 dihydroquinolin-6-yl)methyl]ethenesulfonamide 3.066 (E)-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.88 337 A yl)methyl]but-2-ene-1-sulfonamide 2.060 (E)-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.78 309 A yl)methyl]prop-1-ene-1-sulfonamide 3.062 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.85 325 A yl)methyl]propane-1-sulfonamide 2.067 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-3,3,3- 0.86 365 A trifluoro-propane-1-sulfonamide 3.067 3,3,3-trifluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.91 379 A 132-135 yl)methyl]propane-1-sulfonamide 2.068 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6- 0.85 351 A 128-131 yl)methyl]thiophene-3-sulfonamide 3.068 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.88 365 A 150-154 yl)methyl]thiophene-3-sulfonamide 2.052 (E)-2-(4-bromophenyl)-N-[(1-ethyl-2-oxo-3,4- 0.96 451 A 119-124 dihydroquinolin-6-yl)methyl]ethenesulfonamide 2.069 (E)-2-(3-chlorophenyl)-N-[(1-ethyl-2-oxo-3,4- 0.93 405 A 149-151 dihydroquinolin-6-yl)methyl]ethenesulfonamide 2.020 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-4,4,4- 0.85 379 A trifluoro-butane-1-sulfonamide 2.070 (E)-2-(3-bromophenyl)-N-[(1-ethyl-2-oxo-3,4- 0.97 451 A 144-147 dihydroquinolin-6-yl)methyl]ethenesulfonamide 3.069 (E)-2-(3-chlorophenyl)-N-[(2-oxo-1-propyl-3,4- 0.98 419 A 129-133 dihydroquinolin-6-yl)methyl]ethenesulfonamide 3.070 (E)-2-(3-bromophenyl)-N-[(2-oxo-1-propyl-3,4- 1.00 465 A 148-153 dihydroquinolin-6-yl)methyl]ethenesulfonamide 3.060 (E)-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.84 323 A 95-99 yl)methyl]prop-1-ene-1-sulfonamide 3.020 4,4,4-trifluoro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.91 393 A yl)methyl]butane-1-sulfonamide 3.056 (E)-2-(2-fluorophenyl)-N-[(2-oxo-1-propyl-3,4- 0.95 403 A 169-173 dihydroquinolin-6-yl)methyl]ethenesulfonamide 2.051 (E)-N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2- 0.87 371 A 134-137 phenyl-ethenesulfonamide 2.061 N-[(1-ethyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-5- 0.87 365 A 149-152 methyl-thiophene-2-sulfonamide 3.064 2,5-dichloro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 1.00 433 A 131-134 yl)methyl]thiophene-3-sulfonamide 3.071 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methyl]prop- 0.80 323 A 2-ene-1-sulfonamide 16.001 N-[(1-ethyl-4,8-dimethyl-2-oxo-3,4-dihydroquinolin-6- 0.93 373 A yl)methyl]benzenesulfonamide 9.001 N-[[2-oxo-1-(3-pyridyl)-3,4-dihydroquinolin-6- 0.78 394 A yl]methyl]benzenesulfonamide 8.001 N-[(2-oxo-1-phenyl-3,4-dihydroquinolin-6- 0.91 393 A yl)methyl]benzenesulfonamide 8.006 2,4-difluoro-N-[(2-oxo-1-phenyl-3,4-dihydroquinolin-6- 0.94 429 A yl)methyl]benzenesulfonamide 7.009 4-fluoro-N-[(2-oxo-1-propyl-6- 0.86 376 A quinolyl)methyl]benzenesulfonamide 7.001 2,4-difluoro-N-[(2-oxo-1-propyl-6- 0.85 357 A quinolyl)methyl]benzenesulfonamide 7.006 2,4-difluoro-N-[(2-oxo-1-propyl-6- 0.88 393 A quinolyl)methyl]benzenesulfonamide 13.006 2,4-difluoro-N-[[1-(2-methoxyethyl)-2-oxo-3,4- 0.86 411 A dihydroquinolin-6-yl]methyl]benzenesulfonamide 13.001 N-[[1-(2-methoxyethyl)-2-oxo-3,4-dihydroquinolin-6- 0.83 375 A yl]methyl]benzenesulfonamide 5.006 N-[(1-allyl-2-oxo-3,4-dihydroquinolin-6-yl)methyl]-2,4- 0.9 393 A difluoro-benzenesulfonamide 5.001 N-[(1-allyl-2-oxo-3,4-dihydroquinolin-6- 0.88 357 A yl)methyl]benzenesulfonamide 11.006 2,4-difluoro-N-[[2-oxo-1-(2,2,2-trifluoroethyl)-3,4- 0.94 435 A dihydroquinolin-6-yl]methyl]benzenesulfonamide 11.001 N-[[2-oxo-1-(2,2,2-trifluoroethyl)-3,4-dihydroquinolin-6- 0.92 399 A yl]methyl]benzenesulfonamide 10.006 N-[[1-(cyclopropylmethyl)-2-oxo-3,4-dihydroquinolin-6- 0.94 407 A yl]methyl]-2,4-difluoro-benzenesulfonamide 10.001 N-[[1-(cyclopropylmethyl)-2-oxo-3,4-dihydroquinolin-6- 0.92 371 A yl]methyl]benzenesulfonamide 22.001 N-[(1-ethyl-8-fluoro-4-methyl-2-oxo-3,4-dihydroquinolin- 0.91 377 A 6-yl)methyl]benzenesulfonamide 3.073 5-chloro-N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.97 399 A 144-147 yl)methyl]thiophene-2-sulfonamide 3.072 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.88 365 A 151-153 yl)methyl]thiophene-2-sulfonamide 17.001 N-[(8-fluoro-2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 377 A yl)methyl]benzenesulfonamide 3.074 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.96 409 A 176-179 yl)methyl]naphthalene-1-sulfonamide 3.075 N-[(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.96 409 A 169-173 yl)methyl]naphthalene-2-sulfonamide 14.006 2,4-difluoro-N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.95 409 A yl)ethyl]benzenesulfonamide 14.009 4-fluoro-N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.94 391 A yl)ethyl]benzenesulfonamide 14.001 N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 373 A yl)ethyl]benzenesulfonamide 15.006 2,4-difluoro-N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.96 421 A yl)cyclopropyl]benzenesulfonamide 15.009 4-fluoro-N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.95 403 A yl)cyclopropyl]benzenesulfonamide 15.001 N-[1-(2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 385 A yl)cyclopropyl]benzenesulfonamide 20.006 N-[(1-ethyl-4-methyl-2-oxo-3,4-dihydroquinolin-6- 0.95 395 A yl)methyl]-2,4-difluoro-benzenesulfonamide 20.001 N-[(1-ethyl-4-methyl-2-oxo-3,4-dihydroquinolin-6- 0.87 359 A yl)methyl]benzenesulfonamide 23.001 N-[[4-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-3,4- 0.95 413 A dihydroquinolin-6-yl]methyl]benzenesulfonamide 23.006 2,4-difluoro-N-[[4-methyl-2-oxo-1-(2,2,2-trifluoroethyl)- 0.97 449 A 3,4-dihydroquinolin-6-yl]methyl]benzenesulfonamide 24.001 N-[[1-(cyclopropylmethyl)-4-methyl-2-oxo-3,4- 0.96 385 A dihydroquinolin-6-yl]methyl]benzenesulfonamide 24.006 N-[[1-(cyclopropylmethyl)-4-methyl-2-oxo-3,4- 0.98 421 A dihydroquinolin-6-yl]methyl]-2,4-difluoro- benzenesulfonamide 25.001 N-[(1-allyl-4-methyl-2-oxo-3,4-dihydroquinolin-6- 0.92 371 A yl)methyl]benzenesulfonamide 25.006 N-[(1-allyl-4-methyl-2-oxo-3,4-dihydroquinolin-6- 0.92 407 A yl)methyl]-2,4-difluoro-benzenesulfonamide 26.001 N-[(7-fluoro-2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.93 377 A yl)methyl]benzenesulfonamide 27.001 N-[(5-fluoro-2-oxo-1-propyl-3,4-dihydroquinolin-6- 0.92 377 A yl)methyl]benzenesulfonamide
MethodA:

(50) Spectra were recorded on a Mass Spectrometer from Waters (SQD or ZQ Single quadrupole mass spectrometer) equipped with an electrospray source (Polarity: positive or negative ions, Capillary: 3.00 kV, Cone range: 30-60 V, Extractor: 2.00 V, Source Temperature: 150 C., Desolvation Temperature: 350 C., Cone Gas Flow: 0 L/Hr, Desolvation Gas Flow: 650 L/Hr, Mass range: 100 to 900 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 m, 302.1 mm, Temp: 60 C., DAD Wavelength range (nm): 210 to 500, Solvent Gradient: A=water+5% MeOH+0.05% HCOOH, B=Acetonitrile+0.05% HCOOH: gradient: 0 min 0% B, 100% A; 1.2-1.5 min 100% B; Flow (ml/min) 0.85

(51) MethodB:

(52) Spectra were recorded on a Mass Spectrometer from Waters SQD 2 equipped with an electrospray source (Polarity: positive ions, Capillary: 3.5 kV, Cone range: 30 V, Extractor: 3.00 V, Source Temperature: 150 C., Desolvation Temperature: 400 C., Cone Gas Flow: 60 L/Hr, Desolvation Gas Flow: 700 L/Hr, Mass range: 140 to 800 Da) and an Acquity UPLC from Waters: Binary pump, heated column compartment and diode-array detector. Solvent degasser, binary pump, heated column compartment and diode-array detector. Column: Waters UPLC HSS T3, 1.8 micron, 302.1 mm, Temp: 60 C., DAD Wavelength range (nm): 210 to 400, Solvent Gradient: A=water+5% MeOH+0.1% HCOOH, B=Acetonitrile+0.1% HCOOH; gradient: 0 min 100% A; 2.5 min 100% B; 2.8 min 100% B; 3.0 min 100% A; Flow (ml/min) 0.75.

BIOLOGICAL EXAMPLES

(53) A) Reduced Plant Water Use in Soybean

(54) Compounds were tested for their effect on reducing plant water use as follows. Each compound was dissolved in a blank emulsifiable concentrate (EC) formulation that was then diluted to the desired concentration with water containing additional surfactant (EXTRAVON 1 g/20 L). The compounds were applied by foliar spray to 12 day old soybean plants (variety S20-G7) grown in controlled environment plant growth chambers. Plant water use during the day was assessed by repeated weighing of the pots in which the plants were grown before and after application of the compounds at the indicated times (expressed in days after application (DAA)). The water use data before application was used to correct any differences in water use arising due to non-treatment effects (e.g. due to differences in plant size). The untransformed water use values were subjected to an analysis of covariance, fitting the effect of treatment and using the baseline water use 1 day before application as a covariate.

(55) The results are expressed compared to negative control treatment (diluted EC formulation without active ingredient but with EXTRAVON 1 g/20 L).

(56) Application of the chemicals (0 DAA) takes place approximately between 08:00 and 09:30 a.m. WU is measured within day time (chamber light is on 06:00 to 20:00) at these timepoints: 0 DAA a.m. (10:30-12:50), 0 DAA p.m. (14:00-19:50), 1 DAA a.m. (7:30-12:50), 1 DAA p.m. (14:00-19:50), 2 DAA a.m. (07:30-12:50) and 2 DAA p.m. (14:00-19:50). The cumulative total WU (0-2.5 DAA) is calculated by summing the WU data mentioned above.

(57) TABLE-US-00003 TABLE B1 Percent increase or decrease of water use (WU) during day time of soybean plants sprayed with the indicated compounds at 500 M compared to a negative control treatment (e.g. 0 = identical to negative control; 8.5 = 8.5% decrease in water use compared to negative control treatment). Average WU values of 6 pots (each with three plants) per treatment are shown. % WU 0 DAA 0DAA 1DAA 1DAA 2 DAA 2 DAA Total 0 to Compounds AM PM AM PM AM PM 2.5 DAA Untreated Control 0 0 0 0 0 0 0 3.005 37.5 32.9 24.9 21.9 12.9 12.0 21.9 2.010 15.2 5.7 2.6 1.7 3.6 2.4 4.3 3.016 3.6 5.8 1.3 0.5 1.1 0 1.2 3.012 43.9 17.8 1.8 2.1 1.7 3.0 5.8 2.001 35.3 34.3 29.1 28.1 19.6 14.3 25.7 3.001 15.0 13.1 9.9 6.7 7.2 5.8 8.8 3.007 16.1 14.1 12.7 9.7 7.7 7.6 10.8 3.006 36.5 35.8 28.3 24.2 17.8 14.9 24.5 3.009 17.5 14.9 9.4 6.4 5.5 4.2 8.5 3.011 3.6 4.0 3.6 2.3 3.6 2.4 3.0 3.010 28 12.5 3.0 1.0 2.1 1.7 5.7 2.007 14.1 9.5 7.3 6.6 8.8 5.7 8.1 2.009 5.3 3.0 2.0 1.2 3.1 1.0 2.3 2.006 23.4 17.6 13.8 13.0 10.4 7.3 13.2 2.014 2.8 0.7 0.2 0.9 0.9 1.7 1.1 3.002 22.5 20.6 13.7 9.4 6.7 4.7 11.4 2.002 10.4 8.5 6.5 4.0 5.6 4.2 5.8 2.068 27.0 22.4 18.1 14.7 11.6 7.5 15.3 3.068 46.0 46.5 39.3 31.6 22.3 15.3 31.6 3.060 7.9 4.6 5.8 2.6 5.4 2.7 4.6 3.063 9.3 4.7 5.1 3.9 6.6 5.0 5.5 3.064 34.7 29.8 23.3 21.3 17.2 13.5 22.2 2.061 50.4 38.6 7.9 2.2 0.5 1.2 13.7 3.061 47.8 22.2 +1 +3.4 +1.6 1.2 13.7 3.020 19.3 12.3 10.1 5.5 7.4 4.2 8.5 3.067 28.4 24.3 19.3 17.2 13.3 9.5 17.2 3.074 8.6 3 0 +1 1.5 0 1.4 3.075 10.8 5.8 2.1 0.6 2.1 2 3.3 15.001 27.4 24.2 14.9 13.9 9.5 7.2 15.1 15.006 32.6 32.2 23.6 24.4 17 17.8 23.8 17.001 41.6 43.1 38 36.3 27.1 26.3 34.7 20.001 50.1 54 58.5 55.2 55.8 50.5 54.4 3.072 39.4 42.4 45.9 40.9 39.8 32.2 40.1 3.073 44.6 47.9 54.9 52.1 53.3 48.7 51 22.001 46.1 48.5 55.8 53 55.1 50.1 52.1 5.001 15.1 19.2 18.7 17.4 16.5 15.6 17.1 5.006 13.6 13.6 12.5 11.5 9.7 9.9 11.4 7.001 17.1 14.1 9.1 6.9 6.9 2.5 8.8 7.006 14.6 12.2 6.7 4.2 4.2 0 6.1 7.009 8.1 7.4 3.6 3.5 4 1.7 4.1 10.001 25.2 27.8 23.8 22.7 14.9 14.7 20.8 10.006 22.4 20.3 18.5 18.2 16.9 17.8 18.6 11.001 20.8 24.4 26.2 27.6 26.9 26.9 26.1 11.006 13 14.7 15.3 15.7 16.4 16.5 15.8 13.001 15.1 14.3 11 11 8.9 9.2 11.1 13.006 9.8 10.2 9.3 10.1 9.6 10.3 10.1 16.001 39 44.8 49 48.1 45.7 44.5 46 24.001 35.3 40.3 42.8 42.8 39.9 38.3 40.6 23.001 31.3 36.9 39.7 40.8 35.9 37.3 37.7 25.001 28.2 37.2 41 39.6 38.1 36.7 37.9

(58) The results show that soy plants treated with compounds of the present invention use less water than untreated plants.

(59) TABLE-US-00004 TABLE B2 Percent increase or decrease of water use (WU) during day time of soybean plants sprayed with the indicated compounds at indicated rate compared to a negative control treatment (e.g. 0 = identical to negative control; 8.5 = 8.5% decrease in water use compared to negative control treatment). Average WU values of 6 pots (each with three plants) per treatment are shown. % WU 0 DAA 0DAA 1DAA 1DAA 2 DAA 2 DAA Total 0 to Compounds Rate AM* PM AM PM AM PM 2.5 DAA Quinabactin 0.3 0.3 0.2 0.1 0.9 1.3 0.7 2.001 31.25 uM 0.7 1.4 1.8 0.9 2.7 1.5 1.7 3.001 4.4 7.7 6.9 5.4 5.8 2.2 5.7 Quinabactin 15.3 5.7 1.8 2.9 2.4 1.1 0.5 2.001 125 uM 10.4 11.5 10.1 10.9 11.7 10.1 11.1 3.001 23.7 23.7 15.7 15.3 9.3 6.3 14.8 Quinabactin 42.0 41.2 18.6 10.8 3.8 2.9 16.9 2.001 500 uM 41.2 43.4 36.3 33.2 24.2 19.5 31.8 3.001 44.6 45.5 36.4 33.3 21.4 15.1 31.1

(60) The results show that plants treated with compounds of the present invention use less water than plants treated with control compound quinabactin.

(61) B) Reduced Plant Water Use in Corn

(62) Compounds were tested for their effect on reducing plant water use as follows. The compounds were applied by foliar spray to 12 day old corn plants (variety NK OCTET) grown in controlled environment plant growth chambers. All compounds were applied using an emulsifiable concentrate (EC) formulation that was diluted to the desired concentrations with water containing 0.4% of the adjuvant rape seed methyl ester. Plant water use during the day was assessed by repeated weighing of the pots in which the plants were grown before and after application of the compounds at the indicated times (expressed in days after application (DAA)). The water use data before application was used to correct any differences in water use arising due to non-treatment effects (e.g. due to differences in plant size). The untransformed water use values were subjected to an analysis of covariance, fitting the effect of treatment and using the baseline water use 1 day before application as a covariate.

(63) Application of the chemicals (0 DAA) takes place approximately between 08:00 and 09:30 a.m. WU is measured within day time (chamber light is on 06:00 to 20:00) at these timepoints: 0 DAA a.m. (10:30-12:50), 0 DAA p.m. (14:00-19:50), 1 DAA a.m. (07:30-12:50), 1 DAA p.m. (14:00-19:50), 2 DAA a.m. (07:30-12:50) and 2 DAA p.m. (14:00-19:50). The cumulative total WU (0-2.5 DAA) is calculated by summing the WU data mentioned above.

(64) TABLE-US-00005 TABLE B3 Percent increase or decrease of water use (WU) during day time of corn plants sprayed with the indicated compounds at 500 M compared to a negative control treatment (e.g. 0 = identical to negative control; 8.5 = 8.5% decrease in water use compared to negative control treatment). Average WU values of 6 pots (each with three plants) per treatment are shown. % WU 0 DAA 0DAA 1DAA 1DAA 2 DAA 2 DAA Total 0 to Compounds AM PM AM PM AM PM 2.5 DAA Untreated Control 0 0 0 0 0 0 0 2.002 10.8 3.6 3.2 3.9 1.2 1.7 3.2 2.006 12.5 6.7 6.5 5.5 3.0 3.2 5.4 2.015 8.9 3.4 4.0 2.6 1.9 1.0 2.9 2.051 13.2 8.5 10.7 8.6 8.7 6.5 9.1 2.068 16.6 15.1 12.9 11.4 9.2 9.1 11.8 2.069 6.5 3.5 3.3 3.7 2.1 1.9 3.2 2.070 8.1 4.1 6.1 5.5 4.8 3.8 5.0 3.002 16.3 12.2 13.4 10.5 9.5 7.0 10.9 3.004 17.3 12.5 14.1 12.9 11.8 10.7 12.8 3.005 16.2 10.5 9.2 7.9 5.4 5.3 8.2 3.006 18.0 14.1 12.6 10.2 6.6 5.7 10.3 3.007 16.0 12.0 11.4 9.5 6.6 5.9 9.4 3.009 16.9 13.9 13.2 11.9 9.0 8.2 11.6 3.010 14.4 8.3 6.3 5.4 2.5 2.2 5.5 3.017 5.8 3.1 3.1 2.5 1.8 2.1 2.7 3.020 19.2 13.7 14.8 12.1 11.5 8.5 12.7 3.051 11.2 6.4 8.1 5.5 5.4 4.3 6.2 3.052 9.6 4.6 4.5 4.5 2.2 2.5 4.1 3.053 8.0 3.7 4.1 3.6 2.9 2.4 3.6 3.056 8.4 2.7 5.6 4.4 4.7 3.2 4.6 3.060 14.8 10.0 10.6 8.4 8.2 6.4 9.3 3.062 17.8 13.0 13.0 9.8 8.1 6.3 10.5 3.063 8.4 3.1 3.0 1.0 1.5 +2 1.4 3.064 12.6 14.2 11.6 9.9 5.6 4.7 9.3 2.061 18.8 10.8 7.5 2.8 1.6 0.8 6.2 3.061 20.8 19.1 9.5 7.5 2.8 3.9 9 3.066 10.8 7.1 7.1 6.8 4.7 5.5 6.4 3.067 14.7 10.7 12.1 11.5 9.9 10.1 11.1 3.068 25.5 24.9 15.8 13.1 8.9 9.4 14.8 3.069 8.1 4.1 6.1 5.5 4.8 3.8 5.0 3.071 11.2 6.5 4.5 4.7 3.5 2.4 4.9 3.075 9.8 7.9 8.2 6.4 4.9 3.3 6.3 15.001 8.2 6.5 6.5 3.5 2.8 1.8 4.3 15.006 10.2 3 1.4 0.1 1.7 1.1 1.2 15.009 10.7 7.8 8.7 5.8 5.4 5.7 7.1 20.001 21.7 18.3 19.2 10.3 8.1 5.5 12.9 20.006 15.5 14.5 13.2 7 5.7 4.3 9.4

(65) The results show that corn plants treated with compounds of the present invention use less water than untreated plants.