HERBICIDAL COMPOUNDS

Abstract

The present invention relates to compounds of Formula (I) or an agronomically acceptable salt of said compounds wherein Q, R.sup.1, R.sup.2, n and m are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I) and to the use of compounds of Formula (I) for controlling weeds, in particular in crops of useful plants.

##STR00001##

Claims

1. A compound of Formula (I): ##STR00071## or an agronomically acceptable salt thereof, wherein Q is a 5-membered aromatic heterocyclic ring which is optionally substituted by 1 or 2 R.sup.3 substituents independently selected from the group consisting of C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, cyclopropyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.2alkoxy-, C.sub.1-C.sub.2haloalkoxy-, halogen, —C(O)C.sub.1-C.sub.4alkyl, NO.sub.2, —CH.sub.2CN, —CN and —S(O).sub.pC.sub.1-C.sub.4alkyl; each R.sup.1 is independently selected from the group consisting of halogen, —CN, nitro, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy-, C.sub.1-C.sub.4haloalkoxy- and —S(O).sub.pC.sub.1-C.sub.4alkyl; each R.sup.2 is independently selected from the group consisting of halogen, —CN, NO.sub.2, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.3-C.sub.6cycloalkyl C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, —S(O).sub.pC.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy, —C(O)C.sub.1-C.sub.4alkyl, —C(O)OC.sub.1-C.sub.4alkyl and C.sub.1-C.sub.4haloalkoxy; m=0, 1 or 2; n=0, 1 or 2; and p=0, 1 or 2.

2. The compound of Formula (I) according to claim 1, wherein Q is selected from the group consisting of ##STR00072## ##STR00073## ##STR00074## ##STR00075## ##STR00076## wherein R.sup.3 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4alkyl, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, cyclopropyl, C.sub.1-C.sub.2haloalkyl, C.sub.1-C.sub.2alkoxy-, C.sub.1-C.sub.2haloalkoxy-, halogen, —C(O)C.sub.1-C.sub.4alkyl, NO.sub.2, —CH.sub.2CN, —CN and —S(O).sub.pC.sub.1-C.sub.4alkyl; and R.sup.3a is hydrogen or C.sub.1-C.sub.2 alkyl with the proviso that Q is not 1,3,4-oxadiazol-2-yl or a C-linked tetrazolyl and wherein if Q is 2-thienyl or 2-furyl then said 2-thienyl or 2-furyl is substituted by 1 or 2 R.sup.3 independently selected from the group consisting of C.sub.1-C.sub.2haloalkyl, halogen and —CN.

3. The compound of Formula (I) according to claim 1, wherein Q is selected from the group consisting of Q19, Q20 and Q34.

4. The compound of Formula (I) according to claim 1, wherein Q is Q20.

5. The compound according to claim 1, wherein n is 1 and R.sup.1 is fluorine.

6. The compound according to claim 5, wherein R.sup.1 is 3-fluoro.

7. The compound according to claim 1, wherein m is 1 or 2 and R.sup.2 is independently selected from the group consisting of fluorine, nitro, cyano and trifluoromethyl.

8. The compound according to claim 1, wherein R.sup.3 is difluoromethyl or trifluoromethyl.

9. A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.

10. The herbicidal composition according to claim 9, further comprising at least one additional pesticide.

11. The herbicidal composition according to claim 10, wherein the additional pesticide is a herbicide or herbicide safener.

12. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 9.

13. Use of a compound of Formula (I) as defined in claim 1 as a herbicide.

Description

EXAMPLE 1: SYNTHESIS OF 5-[2-[(5-CHLORO-3-FLUORO-2-PYRIDYL)OXY]-6-FLUORO-PHENYL]-3-(DIFLUOROMETHYL)ISOXAZOLE (A1)

[0096] ##STR00026##

[0097] To a stirred solution of 2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenol (0.06 g, 0.26 mmol) in N-dimethylformamide (1.8 mL) was added K.sub.2CO.sub.3 (0.18 g, 1.3 mmol) followed by 5-chloro-2,3-difluoro-pyridine (0.049 g, 0.33 mmol). The reaction was stirred overnight at RT and then heated to 80° C. for 4 hours. The reaction mixture was cooled to RT, diluted with DCM and acidified with 2M HCl, the phases were separated then the aqueous was re-extracted with DCM and the combined organics evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0-10% ethyl acetate in isohexane as eluent to give the desired product as a white solid (0.066 g, 70%).

[0098] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.83 (d, 1H), 7.57 (d, 2H), 7.24-7.08 (m, 2H), 6.94-6.61 (m, 2H)

EXAMPLE 2: SYNTHESIS OF 3-(DIFLUOROMETHYL)-5-[2-FLUORO-6-[(5-NITRO-2-PYRIDYL)OXY]PHENYL]ISOXAZOLE (A2)

[0099] ##STR00027##

[0100] To a stirred solution of the 2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenol (0.06 g, 0.26 mmol) in N,N-dimethylformamide (1.8 mL) was added K.sub.2CO.sub.3 (0.18 g, 1.3 mmol) followed by 2-chloro-5-nitro-pyridine (0.052 g, 0.33 mmol). The reaction was stirred overnight at RT, then diluted with DCM and acidified with 2M HCl, the phases were separated then the aqueous was re-extracted with DCM and the combined organics evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography on silica gel using a gradient of 0-20% ethyl acetate in isohexane as eluent to give the desired product as a colourless oil (0.078 g, 85%).

[0101] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 8.95 (d, 1H), 8.64-8.43 (m, 1H), 7.59 (dt, 1H), 7.32-7.10 (m, 3H), 6.97-6.53 (m, 2H)

EXAMPLE 3: SYNTHESIS OF 2-[2-[(5-CHLORO-3-FLUORO-2-PYRIDYL)OXY]-6-FLUORO-PHENYL]-5-(TRIFLUOROMETHYL)OXAZOLE (A3)

[0102] ##STR00028##

[0103] To a stirred solution of 3-(2-fluoro-6-hydroxy-phenyl)-5-(trifluoromethyl)-4H-isoxazol-5-ol (0.100 g, 0.377 mmol) in DMF (5 mL) was added K.sub.2CO.sub.3 (0.317 g, 2.26 mmol) and 5-chloro-2,3-difluoropyridine (0.141 g, 0.943 mmol). The reaction was heated at 80° C. for 4 hours and then allowed to cool to RT. The reaction mixture was diluted with EtOAc and H.sub.2O, the phases were separated and the aqueous phase was extracted with further EtOAc. The combined organics were washed with H.sub.2O, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude residue was purified by flash chromatography over silica gel using 0-10% EtOAc/isohexane as eluent to give the desired product (0.068 g, 48%) as a pale yellow solid.

[0104] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.78 (d, 1H), 7.67-7.42 (m, 3H), 7.24-7.05 (m, 2H).

EXAMPLE 4: SYNTHESIS OF 5-NITRO-2-[2-[4-(TRIFLUOROMETHYL)PYRAZOL-1-YL]PHENOXY]PYRIDINE (A14)

Step 1: Synthesis of 1-(2-methoxyphenyl)-4-(trifluoromethyl)pyrazole

[0105] ##STR00029##

[0106] To a stirred solution of l-bromo-2-methoxy-benzene (0.20 g, 1.07 mmol) in 1,4-dioxane (4 mL) was added 4-(trifluoromethyl)-1H-pyrazole (0.291 g, 2.14 mmol), CuI (0.204 g, 1.07 mmol), N,N′-dimethylethane-1,2-diamine (0.189 mg, 2.74 mmol) and K.sub.2CO.sub.3 (0.227 g, 1.64 mmol). The reaction was heated at reflux for 72 hours, allowed to cool to room temperature, absorbed onto silica gel and purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in isohexane as eluent to give the desired product (0.169 g, 65%) as a colourless oil.

[0107] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 8.31 (s, 1H), 7.88 (s, 1H), 7.72 (d, 1H), 7.36 (t, 1H), 7.11-7.03 (m, 2H), 3.91 (s, 3H).

Step 2: Synthesis of 2-[4-(trifluoromethyl)pyrazol-1-yl]phenol

[0108] ##STR00030##

[0109] To a stirred solution of 1-(2-methoxyphenyl)-4-(trifluoromethyl)pyrazole (1.25 g, 5.16 mmol) in DCM (100 mL) at 0° C. under an atmosphere of N.sub.2 was added BBr.sub.3 (12.9 mL of a 1M solution in DCM, 12.9 mmol). The reaction mixture was allowed to warm to 15° C. over 2 hours, quenched with water, the pH adjusted to 7 with saturated NaHCO.sub.3 solution and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4, absorbed onto silica gel and purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in isohexane as eluent to give the desired product (1.06 g, 90%) as a white solid.

[0110] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 10.50 (s, 1H), 8.28 (s, 1H), 7.94 (s, 1H), 7.39 (d, 1H), 7.26 (t, 1H), 7.12 (d, 1H), 6.96 (t, 1H).

Step 3: Synthesis of 5-nitro-2-[2-[4-(trifluoromethyl)pyrazol-1-yl]phenoxy]pyridine (A14)

[0111] ##STR00031##

[0112] To a stirred solution of 2-[4-(trifluoromethyl)pyrazol-1-yl]phenol (0.20 g, 0.88 mmol) in DMF (5 mL) was added K.sub.2CO.sub.3 (0.242 g, 1.75 mmol) and 2-chloro-5-nitro-pyridine (0.166 mg, 1.05 mmol). The reaction was heated at 80° C. for 3 hours, allowed to cool to RT, diluted with H.sub.2O and extracted with Et.sub.2O (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give a brown solid. The crude product was purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in isohexane as eluent to give the desired product (0.078 g, 26%) as a pale yellow solid.

[0113] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 8.91 (s, 1H), 8.45 (dd, 1H), 8.02 (s, 1H), 7.79-7.70 (m, 2H), 7.55-7.49 (m, 1H), 7.49-7.42 (m, 1H), 7.32 (d, 1H), 7.03 (d, 1H)

EXAMPLE 5: SYNTHESIS OF 5-CHLORO-2-[2-(4-CHLOROPYRAZOL-1-YL)PHENOXY]-3-FLUORO-PYRIDINE (A24)

Step 1: Synthesis of 5-chloro-3-fluoro-2-(2-iodophenoxy)pyridine

[0114] ##STR00032##

[0115] To a stirred solution of 2-iodo phenol (6.40 g, 29.1 mmol) in DMF (64 mL) was added K.sub.2CO.sub.3 (8.04 g, 58.2 mmol) and 5-chloro, 2,3-difluoropyridine (5.22 g, 34.9 mmol) and the reaction heated at 80° C. for 16 hours. The reaction was cooled to RT, diluted with H.sub.2O (200 mL) and extracted with Et.sub.2O (3×75 ml_). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give a yellow oil. The crude product was purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in cyclohexane to give the desired product (10.10 g, 99%) as a colourless oil.

[0116] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.91-7.82 (m, 2H), 7.53 (dd, 1H), 7.41 (t, 1H), 7.18 (d, 1H), 7.01 (t, 1H)

Step 2: Synthesis of 5-chloro-2-[2-(4-chloropyrazol-1-yl)phenoxy]-3-fluoro-pyridine (A24)

[0117] ##STR00033##

[0118] To a stirred solution of 5-chloro-3-fluoro-2-(2-iodophenoxy)pyridine (0.20 g, 0.572 mmol), in 1,4-dioxane (4 mL) was added 4-chloro-1H-pyrazole (0.117 mg, 1.14 mmol), CuI (0.109 g, 0.572 mmol), N,N′-dimethylethane-1,2-diamine (0.108 g, 1.14 mmol) and K.sub.2CO.sub.3 (0.168 g, 1.22 mmol) and the reaction heated at reflux for 16 hours. The reaction was allowed to cool to RT, diluted with H.sub.2O (10 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give a brown oil. The crude product was purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in cyclohexane as eluent to give the desired product (27 mg, 14%) as a white solid.

[0119] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.81 (s, 1H), 7.72 (d, 1H), 7.69 (dd, 1H), 7.48 (s, 1H), 7.42 (dd, 1H), 7.37-7.28 (m, 2H), 7.19 (dd, 1H).

EXAMPLE 6: SYNTHESIS OF 3-[2-[(5-CHLORO-3-FLUORO-2-PYRIDYL)OXY]-6-FLUORO-PHENYL]-5-(TRIFLUOROMETHYL)ISOXAZOLE (A25)

Step 1: Synthesis of 3-fluoro-2-[5-(trifluoromethyl)isoxazol-3-yl]phenol

[0120] ##STR00034##

[0121] To a stirred solution of 3-(2-fluoro-6-hydroxy-phenyl)-5-(trifluoromethyl)-4H-isoxazol-5-ol (20.0 g, 75.4 mmol) in toluene (150 mL) was added p-toluene sulphonic acid monohydrate (1.59 g, 9.05 mmol). The reaction was heated at reflux for 2 h with azeotropic removal of water then cooled to RT and evaporated to dryness under reduced pressure. The residue was dissolved in CH.sub.2Cl.sub.2 (500 ml) and added gradually to a stirred solution of saturated aq. NaHCO.sub.3 (200 ml). The organic phase was separated and washed with H.sub.2O then brine and evaporated to dryness under reduced pressure to leave the desired product (17.41 g, 93%) as an off white solid which was used without further purification.

[0122] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 9.54 (s, 1H), 7.35 (m, 2H), 6.94 (d, 1H), 6.76 (t, 1H).

Step 2: Synthesis of 3-[2-[(5-chloro-3-fluoro-2-pyridyl)oxy]-6-fluoro-phenyl]-5-(trifluoromethyl)isoxazole (A25)

[0123] ##STR00035##

[0124] To a solution of 3-fluoro-2-[5-(trifluoromethyl)isoxazol-3-yl]phenol (1.00 g, 4.05 mmol) in N,N-dimethylformamide (15 mL) was added 5-chloro-2,3-difluoro-pyridine (3.03 g, 20.2 mmol) and potassium carbonate (0.85 g, 6.07 mmol). The reaction was heated at 80° C. for 3.5 hours, allowed to cool to RT and then quenched by addition of H.sub.2O. The reaction was then extracted with EtOAc (×3) and the combined organic extracts washed with H.sub.2O and brine before being dried over MgSO.sub.4, and evaporated to dryness under reduced pressure to leave a yellow oil. The crude product was purified by flash chromatography on silica gel using a gradient of 100% cyclohexane to 10% EtOAc/cyclohexane as eluent to give the desired product (30 mg, 2%) as a pale yellow gum.

[0125] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.81 (s, 1H), 7.54 (m, 2H), 7.15 (t, 1H), 7.10 (d, 1H), 6.99 (s, 1H)

EXAMPLE 7: SYNTHESIS OF 5-CHLORO-3-FLUORO-2-(2-IMIDAZOL-1-YLPHENOXY)PYRIDINE (A28)

Step 1: Synthesis of 1-(2-methoxyphenyl)imidazole

[0126] ##STR00036##

[0127] A mixture of imidazole (0.806 g, 0.012 mol), (2-methoxyphenyl)boronic acid (1.50 g, 0.0099 mol) and Cu(I)Cl (0.100 g, 0.001 mol) in MeOH (50 mL) was heated at reflux overnight. The reaction mixture was allowed to cool to RT and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-5% MeOH/DCM as eluent to give the desired product (133 mg, 7%) as a brown oil.

[0128] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.79 (s, 1H), 7.34 (t, 1H), 7.28 (d, 1H), 7.20 (s, 1H), 7.16 (s, 1H), 7.09-7.00 (m, 2H), 3.84 (s, 3H)

Step 2: Synthesis of 2-imidazol-1-ylphenol

[0129] ##STR00037##

[0130] To a solution of 1-(2-methoxyphenyl)imidazole (55 mg, 0.89 mmol) in dichloromethane (18 mL) at 0° C., under nitrogen, was added dropwise boron tribromide (1M solution in DCM) (2.22 mL, 2.22 mmol) maintaining temperature at <5° C. Once addition was complete, the reaction mixture was allowed to stir at this temperature for 1 hour and then allowed to warm to RT and stirred at RT for 72 hours. The reaction mixture was quenched with water and adjusted to pH 7 with saturated aqueous sodium bicarbonate solution then washed with DCM (×3). An off-white solid precipitated out of the aqueous layer. The solid was filtered off, washed with a little water and dried in a vacuum oven at 40° C. for 3 hours to give the desired product (133 mg, 93%) as a beige solid.

[0131] .sup.1H NMR (400 MHz, CD.sub.3OD) δ=7.92 (s, 1H), 7.38 (s, 1H), 7.30 (d, 1H), 7.22 (t, 1H), 7.09 (s, 1H), 7.01 (d, 1H), 6.93 (t, 1H)

Step 3: Synthesis of 5-chloro-3-fluoro-2-(2-imidazol-1-ylphenoxy)pyridine (A28)

[0132] ##STR00038##

[0133] A mixture of 5-chloro-2,3-difluoro-pyridine (0.149 g, 0.10 mmol), 2-imidazol-1-ylphenol (0.133 g, 0.83 mmol) and K.sub.2CO.sub.3 (0.230 g, 1.66 mmol) in DMF (5 mL) was heated at 90° C. overnight. The reaction mixture was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-5% MeOH in DCM as eluent to give the desired product (0.226 g, 94%) as a yellow oil.

[0134] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.71 (s, 1H), 7.68 (s, 1H), 7.51-7.34 (m, 4H), 7.31 (d, 1H), 7.14 (s, 1H), 7.03 (s, 1H)

EXAMPLE 8: SYNTHESIS OF 3-[(5-CHLORO-3-FLUORO-2-PYRIDYL)OXY]-2-[4-(TRIFLUOROMETHYL)PYRAZOL-1-YL]BENZONITRILE (A33)

Step 1: Synthesis of 3-hydroxy-2-[4-(trifluoromethyl)pyrazol-1-yl]benzonitrile

[0135] ##STR00039##

[0136] To a solution of 2-fluoro-3-hydroxy-benzonitrile (1.0 g, 7.3 mmol) and 4-(trifluoromethyl)-1H-pyrazole (1.1 g, 8.0 mmol) in N,N-dimethylacetamide (15 mL) under a nitrogen atmosphere was added powdered K.sub.2CO.sub.3 (3.1 g, 22 mmol). The resultant mixture was heated at 150° C. for 22 hours. The reaction mixture was allowed to cool to RT, diluted with water and extracted with EtOAc (×4). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness to give an orange liquid. The crude product was purified by flash chromatography on silica gel using a gradient of 20 to 40% EtOAc in cyclohexane as eluent to give the desired product (594 mg, 32%) as a yellow solid.

[0137] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=8.64 (s, 1H), 8.07 (s, 1H), 7.42-7.35 (m, 3H).

Step 2: Synthesis of 3-[(5-chloro-3-fluoro-2-pyridyl)oxy]-2-[4-(trifluoromethyl)pyrazol-1-yl]benzonitrile (A33)

[0138] ##STR00040##

[0139] To a solution of 3-hydroxy-2-[4-(trifluoromethyl)pyrazol-1-yl]benzonitrile (0.180 g, 0.711 mmol) and 5-chloro-2,3-difluoro-pyridine (0.138 g, 0.924 mmol) in N,N-dimethylformamide (4.50 mL) was added K.sub.2CO.sub.3 (0.248 g, 1.78 mmol). The mixture was heated under microwave irradiation at 130° C. for 1 hour. The reaction mixture was poured into water and extracted with EtOAc (×3). The combined organic extracts were washed with 1M NaOH solution then brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give a brown liquid. The crude product was purified by flash chromatography on silica gel using a gradient of 0 to 50% EtOAc in cyclohexane as eluent to give the desired product (0.191 g, 63%) as a white solid.

[0140] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=8.03 (s, 1H), 7.87 (s, 1H), 7.78 (d, 1H), 7.75 (dd, 1H), 7.64 (d, 1H), 7.63 (s, 1H), 7.48 (dd, 1H)

EXAMPLE 9: SYNTHESIS OF 5-CHLORO-3-FLUORO-2-[3-METHOXY-2-[4-(TRIFLUOROMETHYL)PYRAZOL-1-YL]PHENOXY]PYRIDINE (A36)

Step 1: Synthesis of 1-(2-methoxyphenyl)-4-(trifluoromethyl)pyrazole

[0141] ##STR00041##

[0142] A solution of 4-(trifluoromethyl)-1H-pyrazole (291 mg, 2.14 mmol), 1-bromo-2-methoxy-benzene (200 mg, 1.07 mmol), Cu(I)I (204 mg, 1.07 mmol), N,N′-dimethylethane-1,2-diamine (188 mg, 2.14 mmol) and K.sub.2CO.sub.3 (227 mg, 2.25 mmol) in 1,4-dioxane (20 mL) was heated at reflux for 18 hours. The reaction was allowed to cool to RT and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 5-50% EtOAc in cyclohexane as eluent to give the desired product (169 mg, 65%) as a colourless oil.

[0143] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=8.31 (s, 1H), 7.88 (s, 1H), 7.72 (d, 1H), 7.36 (t, 1H), 7.11-7.03 (m, 2H), 3.91 (s, 3H).

Step 2: Synthesis of [3-methoxy-2-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetate

[0144] ##STR00042##

[0145] A solution of 1-(2-methoxyphenyl)-4-(trifluoromethyl)pyrazole (326 mg, 1.35 mmol), Pd(OAc).sub.2 (31 mg, 0.13 mmol) and (diacetoxyiodo)benzene (1.77 g, 5.38 mmol) in acetic acid (13.5 mL) was heated at 100° C. for 2 hours. The reaction was allowed to cool to RT, then evaporated to dryness under reduced pressure and azeotroped three times with toluene. The crude product was purified by flash chromatography on silica gel using a gradient of 5-100% EtOAc in cyclohexane as eluent to give the desired product (292 mg, 72%) as a yellow solid.

[0146] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.90 (s, 1H), 7.81 (s, 1H), 7.46 (t, 1H), 6.95 (d, 1H), 6.85 (d, 1H), 3.83 (s, 3H), 2.08 (s, 3H)

Step 3: Synthesis of 3-methoxy-2-[4-(trifluoromethyl)pyrazol-1-yl]phenol

[0147] ##STR00043##

[0148] A solution of [3-methoxy-2-[4-(trifluoromethyl)pyrazol-1-yl]phenyl]acetate (295 mg, 0.95 mmol) and NaOH (133 mg, 3.32 mmol) in MeOH (5.7 mL) and H.sub.2O (0.57 mL) was stirred at RT overnight. The reaction was diluted with water, made acidic with 2M HCl and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give the desired product (245 mg, quant) which was used without further purification.

[0149] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=10.1 (br, 1H), 8.52 (s, 1H), 7.91 (s, 1H), 7.17 (t, 1H), 6.74 (d, 1H), 6.59 (d, 1H), 3.91 (s, 3H)

Step 4: Synthesis of 5-chloro-3-fluoro-2-[3-methoxy-2-[4-(trifluoromethyl)pyrazol-1-yl]phenoxy]pyridine (A36)

[0150] ##STR00044##

[0151] A solution of 3-methoxy-2-[4-(trifluoromethyl)pyrazol-1-yl]phenol (150 mg, 0.58 mmol), 5-chloro-2,3-difluoro-pyridine (104 mg, 0.70 mmol) and K.sub.2CO.sub.3 (161 mg, 1.16 mmol) in DMF (2 mL) was heated at 80° C. for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 5-30% EtOAc in cyclohexane as eluent to give the desired product (169 mg, 75%) as a colourless gum.

[0152] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.78 (s, 1H), 7.72 (s, 2H), 7.47 (t, 1H), 7.39 (dd, 1H), 7.00-6.91 (m, 2H), 3.83 (s, 3H)

EXAMPLE 10: SYNTHESIS OF 5-CHLORO-3-FLUORO-2-[3-IODO-2-[4-(TRIFLUOROMETHYL)PYRAZOL-1-YL]PHENOXY]PYRIDINE (A57)

Step 1: Synthesis of 1-(2-iodo-6-methoxy-phenyl)-4-(trifluoromethyl)pyrazole

[0153] ##STR00045##

[0154] A solution of 1-(2-methoxyphenyl)-4-(trifluoromethyl)pyrazole (270 mg, 1.11 mmol), Pd(OAc).sub.2 (26 mg, 0.11 mmol) and N-iodosuccinimide (284 mg, 1.23 mmol) in acetic acid (11.5 mL) was heated at 100° C. for 2 hours. The reaction was allowed to cool to RT, then evaporated to dryness under reduced pressure and azeotroped three times with toluene. The crude product was purified by flash chromatography on silica gel using a gradient of 5-30% EtOAc in cyclohexane as eluent to give the desired product (397 mg, 97%) as a pale yellow gum.

[0155] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.95 (s, 1H), 7.75 (s, 1H), 7.52 (d, 1H), 7.16 (t, 1H), 7.00 (d, 1H), 3.77 (s, 3H)

Step 2: Synthesis of 3-iodo-2-[4-(trifluoromethyl)pyrazol-1-yl]phenol

[0156] ##STR00046##

[0157] To a solution of 1-(2-iodo-6-methoxy-phenyl)-4-(trifluoromethyl)pyrazole (234 mg, 0.64 mmol) in dichloromethane (12.5 mL) under an atmosphere of nitrogen was added BBr.sub.3 (1M solution in DCM) (1.59 mL, 1.59 mmol) dropwise. The reaction mixture was stirred at RT for 2.5 hours, then quenched with water. The reaction was basified with saturated aqueous sodium bicarbonate solution and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give the desired product (228 mg, quant) as a beige solid which was used without further purification.

[0158] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=8.20 (s, 1H), 8.02 (s, 1H), 7.51 (d, 1H), 7.11-7.01 (m, 2H)

Step 3: Synthesis of 5-chloro-3-fluoro-2-[3-iodo-2-[4-(trifluoromethyl)pyrazol-1-yl]phenoxy]pyridine (A57)

[0159] ##STR00047##

[0160] A solution of 3-iodo-2-[4-(trifluoromethyl)pyrazol-1-yl]phenol (228 mg, 0.64 mmol), 5-chloro-2,3-difluoro-pyridine (116 mg, 0.77 mmol) and K.sub.2CO.sub.3 (178 mg, 1.29 mmol) in DMF (2 mL) was heated at 80° C. for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 5-30% EtOAc in cyclohexane as eluent to give the desired product (210 mg, 67%) as a white solid.

[0161] .sup.1H NMR (400 MHz, CDCl.sub.3 δ=7.88 (dd, 1H), 7.80 (dd, 2H), 7.72 (s, 1H), 7.40 (dd, 1H), 7.36-7.22 (m, 2H)

EXAMPLE 11: SYNTHESIS OF 5-CHLORO-2-[2-(5-CHLORO-2-THIENYL)PHENOXY]-3-FLUORO-PYRIDINE (A66)

Step 1: Synthesis of 2-chloro-5-(2-methoxyphenyl)thiophene

[0162] ##STR00048##

[0163] A degassed solution of 1-iodo-2-methoxy-benzene (500 mg, 2.14 mmol), (5-chloro-2-thienyl)boronic acid (416 mg, 2.56 mmol), Pd(OAc).sub.2 (25 mg, 0.11 mmol), 2-Dicyclohexylphosphino-2′-methylbiphenyl (MePhos) (159 mg, 0.43 mmol) and KF (372 mg, 6.41 mmol) in 1,4-dioxane (7.5 mL) under an N.sub.2 atmosphere was heated at reflux for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 5-15% EtOAc in cyclohexane as eluent to give the desired product (438 mg, 91%) as an orange oil.

[0164] .sup.1H NMR (400 MHz, CDCl.sub.3 δ=7.58 (d, 1H), 7.28-7.20 (m, 2H), 7.02-6.92 (m, 2H), 6.88 (d, 1H), 3.92 (s, 3H)

Step 2: Synthesis of 2-(5-chloro-2-thienyl)phenol

[0165] ##STR00049##

[0166] To a solution of 2-chloro-5-(2-methoxyphenyl)thiophene (438 mg, 1.95 mmol) in DCM (39 mL) at room temperature and under an N.sub.2 atmosphere was added dropwise BBr.sub.3 (1M solution in DCM) (4.87 mL, 4.87 mmol). The reaction mixture was stirred for 3 hours and then was quenched with water, made basic with saturated aqueous sodium bicarbonate and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give an orange solid (559 mg) which was used without further purification.

Step 3: Synthesis of 5-chloro-2-[2-(5-chloro-2-thienyl)phenoxy]-3-fluoro-pyridine (A66)

[0167] ##STR00050##

[0168] A stirred solution of the crude 2-(5-chloro-2-thienyl)phenol from step 2 above (559 mg), 5-chloro-2,3-difluoro-pyridine (476 mg, 3.18 mmol) and K.sub.2CO.sub.3 (733 mg, 5.31 mmol) in DMF (5 mL) was heated at 80° C. for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel first using a gradient of 5-25% EtOAc in cyclohexane as eluent and secondly using a gradient of 0-10% EtOAc in cyclohexane to give the desired product (51 mg) as an orange gum.

[0169] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.81 (s, 1H), 7.62 (d, 1H), 7.51 (d, 1H), 7.40-7.22 (m, 2H), 7.19-7.11 (m, 2H), 6.82 (s, 1H)

EXAMPLE 12: SYNTHESIS OF 5-CHLORO-3-FLUORO-2-[2-[4-(TRIFLUOROMETHYL)-2-THIENYL]PHENOXY]PYRIDINE (A97)

Step 1: Synthesis of 2-(2-methoxyphenyl)-4-(trifluoromethyl)thiophene

[0170] ##STR00051##

[0171] A degassed solution of 3-(trifluoromethyl)thiophene (0.56 g, 3.68 mmol), 1-bromo-2-methoxybenzene (0.688 g, 3.68 mmol), K.sub.2CO.sub.3 (0.771 g, 5.52 mmol), Pd(OAc).sub.2 (17 mg, 0.076 mmol), pivalic acid (0.128 mL, 1.10 mmol) and tricyclohexylphosphine tetrafluoroborate (54 mg, 0.147 mmol) in N,N-dimethylacetamide (12 mL) was heated at 100° C. under an atmosphere of N.sub.2 for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified twice by flash chromatography on silica gel both times using a gradient of 0-5% EtOAc in cyclohexane to give the desired product (210 mg, 22%) as a pale yellow oil.

[0172] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.69-7.61 (m, 2H), 7.58 (s, 1H), 7.30 (t, 1H), 7.04-6.97 (m, 2H), 3.94 (s, 3H)

Step 2: Synthesis of 2-[4-(trifluoromethyl)-2-thienyl]phenol

[0173] ##STR00052##

[0174] To a solution of 2-(2-methoxyphenyl)-4-(trifluoromethyl)thiophene (210 mg, 0.81 mmol) in DMF (2.5 mL) under an atmosphere of N.sub.2 were added 1-dodecanethiol (0.397 mL, 1.626 mmol) and lithium t-butoxide (1M in THF) (1.6 mL, 1.6 mmol). The reaction mixture was heated at 100° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-20% EtOAc in cyclohexane as eluent to give the desired product (189 mg, 95%) as a yellow oil.

[0175] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.71 (s, 1H), 7.52 (s, 1H), 7.48 (d, 1H), 7.29-7.20 (m, 1H), 6.97 (t, 1H), 6.91 (d, 1H), 5.34 (s, 1H)

Step 3: Synthesis of 5-chloro-3-fluoro-2-[2-[4-(trifluoromethyl)-2-thienyl]phenoxy]pyridine (A97)

[0176] ##STR00053##

[0177] A solution of 2-[4-(trifluoromethyl)-2-thienyl]phenol (174 mg, 0.71 mmol), 5-chloro-2,3-difluoro-pyridine (128 mg, 0.86 mmol) and K.sub.2CO.sub.3 (197 mg, 1.43 mmol) in DMF (5 mL) was heated at 140° C. for 30 minutes under microwave irradiation. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography twice on silica gel first using a gradient of 0-5% EtOAc in cyclohexane as eluent followed by a gradient of 0-30% DCM in cyclohexane as eluent to give the desired product (136 mg, 51%) as a colourless gum.

[0178] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.80 (s, 1H), 7.69 (d, 1H), 7.61 (s, 1H), 7.52-7.48 (m, 2H), 7.40 (t, 1H), 7.31 (t, 1H), 7.20 (d, 1H)

EXAMPLE 13: SYNTHESIS OF 2-[2-[3,5-BIS(TRIFLUOROMETHYL)PYRAZOL-1-YL]PHENOXY]-5-CHLORO-3-FLUORO-PYRIDINE (A123)

Step 1: Synthesis of 1-(2-methoxyphenyl)-3,5-bis(trifluoromethyl)pyrazole

[0179] ##STR00054##

[0180] A solution of (2-methoxyphenyl)hydrazine hydrochloride (500 mg, 2.86 mmol) and 1,1,1,5,5,5-hexafluoropentane-2,4-dione (596 mg, 2.86 mmol) in EtOH (3.6 mL) and cone. H.sub.2SO.sub.4 (0.1 mL) was heated at reflux for 18 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-50% EtOAc in cyclohexane as gradient to give the desired product (101 mg, 11%) as a yellow oil.

[0181] .sup.1H NMR (400 MHz, CDCl.sub.3 δ=7.52 (t, 1H), 7.34 (d, 1H), 7.09-7.00 (m, 3H), 3.79 (s, 3H)

Step 2: Synthesis of 2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenol

[0182] ##STR00055##

[0183] To a stirred solution of 1-(2-methoxyphenyl)-3,5-bis(trifluoromethyl)pyrazole (101 mg, 0.33 mmol) in dichloromethane (6.5 mL) under an N.sub.2 atmosphere was added boron tribromide (1M solution in DCM) (0.81 mL, 0.81 mmol) dropwise. The reaction was stirred at RT overnight. The reaction mixture was quenched with water and extracted with DCM (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give the desired product (91 mg, 94%) as a yellow gum, which was used without further purification.

[0184] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=7.45-7.30 (m, 2H), 7.18-7.07 (m, 2H), 7.02 (t, 1H), 6.32 (s, 1H)

Step 3: Synthesis of 2-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenoxy]-5-chloro-3-fluoro-pyridine (A123)

[0185] ##STR00056##

[0186] A solution of 2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenol (97 mg, 0.23 mmol), 5-chloro-2,3-difluoro-pyridine (55 mg, 0.35 mmol) and K.sub.2CO.sub.3 (85 mg, 0.61 mmol) in DMF (5 mL) was heated at 140° C. under microwave irradiation for 30 minutes. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-10% EtOAc in cyclohexane as eluent to give the desired product (97 mg, 75%) as a brown gum.

[0187] .sup.1H NMR (400 MHz, CDCl.sub.3 δ=7.84 (s, 1H), 7.61 (t, 1H), 7.52 (d, 1H), 7.45 (d, 1H), 7.43-7.35 (m, 2H), 6.96 (s, 1H)

EXAMPLE 14: SYNTHESIS OF 2-[2-[(5-CHLORO-3-FLUORO-2-PYRIDYL)OXY]PHENYL]THIAZOLE (A147)

Step 1: Synthesis of 2-thiazol-2-ylphenol

[0188] ##STR00057##

[0189] A degassed solution of 2-chlorothiazole (260 mg, 2.18 mmol), (2-hydroxyphenyl)boronic acid (250 mg, 1.81 mmol), Na.sub.2C.sub.03 (576 mg, 5.44 mmol), tetrakis(triphenylphosphine)palladium (21 mg, 0.018 mmol) in toluene (2.5 ml_), EtOH (2.5 mL) and water (1.25 mL) was heated at 160° C. for 30 minutes under microwave irradiation. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-50% EtOAc in cyclohexane as eluent to give the desired product (127 mg, 40%) as a pale green oil.

[0190] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=12.3 (s, 1H), 7.79 (s, 1H), 7.63 (d, 1H), 7.35-7.21 (m, 2H), 7.05 (d, 1H), 6.90 (t, 1H)

Step 2: Synthesis of 2-[2-[(5-chloro-3-fluoro-2-pyridyl)oxy]phenyl]thiazole (A147)

[0191] ##STR00058##

[0192] A solution of 2-thiazol-2-ylphenol (127 mg, 0.72 mmol), 5-chloro-2,3-difluoro-pyridine (129 mg, 0.86 mmol) and K.sub.2CO.sub.3 (198 mg, 1.43 mmol) in DMF (5 mL) was heated at 140° C. for 30 minutes under microwave irradiation. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc (×3). The combined organic extracts were washed with brine, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using a gradient of 0-20% EtOAc in cyclohexane as eluent to give the desired product (208 mg, 95%) as a pale yellow oil.

[0193] .sup.1H NMR (400 MHz, CDCl.sub.3) δ=8.42 (d, 1H), 7.88 (s, 1H), 7.73 (s, 1H), 7.55 (d, 1H), 7.46 (t, 1H), 7.41-7.32 (m, 2H), 7.21 (d, 1H)

TABLE-US-00001 TABLE 1 Examples of herbicidal compounds of the present invention. [00059] .sup.1H NMR (400 Com- MHz, CDCl.sub.3 pound n R.sup.1 Q m R.sup.2 unless stated) A1 1 3-F 5-(3- 2 3-F, 7.83 (d, 1H), 7.57 difluoro- 5-Cl (d, 2H), 7.24-7.08 methyl)- (m, 2H), 6.94-6.61 isoxazole (m, 2H) A2 1 3-F 5-(3- 1 5-NO.sub.2 8.95 (d, 1H), 8.64- difluoro- 8.43 (m, 1H), 7.59 methyl)- (dt, 1H), 7.32-7.10 isoxazole (m, 3H), 6.97-6.53 (m, 2H) A3 1 3-F 2-(5- 2 3-F, 7.78 (d, 1H), 7.67- trifluoro- 5-Cl 7.42 (m, 3H), 7.24- methyl)- 7.05 (m, 2H) oxazole A4 1 3-F 5-(3- 2 3-Cl, 8.07-7.40 (m, 3H), difluoro- 5-Cl 7.23-7.02 (m, 2H), methyl)- 7.00-6.51 (m, 2H) isoxazole A5 1 3-F 5-(3- 1 6-Cl 7.75-7.61 (m, 1H), difluoro- 7.55-7.45 (m, 1H), methyl)- 7.21-7.00 (m, 3H), isoxazole 6.95-6.56 (m, 3H) A6 1 3-F 5-(3- 1 5-CF.sub.3 8.35 (s, 1H), 7.94 difluoro- (d, 1H), 7.60-7.50 methyl)- (m, 1H), 7.23-6.99 isoxazole (m, 3H), 6.80 (s, 1H), 6.75 (t, 1H) A7 1 3-F 5-(3- 1 6-F 7.85-7.77 (m, 1H), difluoro- 7.55-7.47 (m, 1H), methyl)- 7.21-7.02 (m, 2H), isoxazole 6.95-6.57 (m, 4H) A8 1 3-F 5-(3- 1 4-CF.sub.3 8.24 (d, 1H), 7.58- difluoro- 7.50 (m, 1H), 7.26- methyl)- 7.05 (m, 4H), 6.80 isoxazole (s, 1H), 6.75 (t, 1H) A9 1 3-F 5-(3- 1 5-Cl 8.03 (d, 1H), 7.73- difluoro- 7.62 (m, 1H), 7.57- methyl)- 7.43 (m, 1H), 7.19- isoxazole 7.09 (m, 1H), 7.09- 7.03 (m, 1H), 6.99 (d, 1H), 6.80 (d 1H), 6.75 (t, 1H) A10 1 3-F 5-(3- 2 3-F, 7.76 (d, 1H), 7.53- difluoro- 5-F 7.48 (m, 1H), 7.41- methyl)- 7.31 (m, 1H), 7.22- isoxazole 6.98 (m, 2H), 6.88 (d, 1H), 6.75 (t, 1H) A11 1 3-F 5-(3- 2 4-Cl, 7.54-7.49 (m, 1H), difluoro- 6-Cl 7.22-7.12 (m, 1H), methyl)- 7.10-7.05 (m, 2H), isoxazole 6.95 (s, 1H), 6.82 (d, 1H), 6.78 (t, 1H) A12 1 3-F 5-(3- 1 5-CN 8.36 (d, 1H), 7.97 difluoro- (dd, 1H), 7.59- methyl)- 7.51 (m, 1H), 7.29- isoxazole 7.06 (m, 3H), 6.81 (d, 1H), 6.75 (t, 1H) A13 1 3-F 5-(3- 2 3-F, 7.96 (s, 1H), 7.55- difluoro- 4-Cl 7.48 (m, 1H), 7.19- methyl)- 7.00 (m, 3H), 6.81 isoxazole (d, 1H), 6.78 (t, 1H) A14 0 — 4- 1 5-NO.sub.2 8.91 (s, 1H), 8.45 (trifluoro- (dd, 1H), 8.02 (s, methyl)- 1H), 7.79-7.70 (m, pyrazol- 2H), 7.55-7.49 (m, 1-yl 1H), 7.49-7.42 (m, 1H), 7.32 (d, 1H), 7.03 (d, 1H) A15 0 — 4- 1 5-CF.sub.3 8.32 (s, 1H), 8.03 (trifluoro- (s, 1H), 7.89 (dd, methyl)- 1H), 7.79-7.71 (m, pyrazol- 2H), 7.52-7.46 (m, 1-yl 1H), 7.46-7.38 (m, 1H), 7.30 (d, 1H), 7.01 (d, 1H) A16 0 — 4- 2 3-F, 8.18 (s, 1H), 7.81- (trifluoro- 5-Cl 7.73 (m, 3H), 7.51- methyl)- 7.43 (m, 2H), 7.40 pyrazol- (t, 1H), 7.32 (d, 1-yl 1H) A17 0 — 4- 1 5-Cl 8.09 (s, 1H), 8.02 (trifluoro- (d, 1H), 7.80 (s, methyl)- 1H), 7.76 (dd, pyrazol- 1H), 7.62 (dd, 1-yl 1H), 7.49-7.41 (m, 1H), 7.41-7.33 (m, 1H), 7.25 (d, 1H), 6.88 (d, 1H) A18 0 — 4- 2 3-F, 8.20 (s, 1H), 7.81- (trifluoro- 5-F 7.73 (m, 2H), 7.72 methyl)- (s, 1H), 7.49-7.42 pyrazol- (m, 1H), 7.41-7.34 1-yl (m, 1H), 7.34-7.22 (m, 2H) A19 0 — 4- 1 5-CN 8.34 (s, 1H), 8.01 (trifluoro- (s, 1H), 7.90 (dd, methyl)- 1H), 7.79-7.70 (m, pyrazol- 2H), 7.55-7.48 (m, 1-yl 1H), 7.48-7.41 (m, 1H), 7.31 (d, 1H), 7.01 (d, 1H) A20 1 3-F 5-(3- 2 3-F, 7.90 (d, 1H), 7.66 difluoro- 5-Br (dd, 1H), 7.52 (dt, methyl)- 1H), 7.17 (ddd, isoxazole 1H), 7.10 (td, 1H), 6.95-6.57 (m, 2H) A21 1 3-F 5-(3- 2 3-F, 8.11 (dd, 1H), difluoro- 5-CF.sub.3 7.73 (dd, 1H), methyl)- 7.56 (dt, 1H), isoxazole 7.26-7.18 (m, 1H), 7.16 (td, 1H), 6.92-6.57 (m, 2H) A22 1 3-F 5-(3- 2 3-F, 8.73 (d, 1H), 8.32 difluoro- 5-NO.sub.2 (dd, 1H), 7.60 (dt, methyl)- 1H), 7.30-7.22 (m, isoxazole 1H), 7.18 (td, 1H), 6.94-6.56 (m, 2H) A23 1 3-F 5-(3- 2 3-F, 8.08 (d, 1H), 7.79 difluoro- 5-CN (dd, 1H), 7.57 (dt, methyl)- 1H), 7.23 (ddd, isoxazole 1H), 7.15 (td, 1H), 6.97-6.58 (m, 2H) A24 0 — 4- 2 3-F, 7.81 (s, 1H), 7.72 (chloro) 5-Cl (d, 1H), 7.69 (dd, pyrazol- 1H), 7.48 (s, 1H), 1-yl 7.42 (dd, 1H), 7.37-7.28 (m, 2H), 7.19 (dd, 1H) A25 1 3-F 3-(5- 2 3-F, 7.81 (s, 1H), 7.54 trifluoro- 5-Cl (m, 2H), 7.15 (t, methyl)- 1H), 7.10 (d, 1H), isoxazole 6.99 (s, 1H) A26 0 — 4-cyano- 2 3-F, 8.32 (s, 1H), 7.91 pyrazol- 5-Cl (s, 1H), 7.82 (d, 1-yl 1H), 7.79 (dd, 1H), 7.53 (dd, 1H), 7.51-7.45 (m, 1H), 7.45-7.39 (m, 1H), 7.30 (dd, 1H) A27 0 — 4-bromo- 2 3-F, 7.91 (s, 1H), 7.79 pyrazol- 5-Cl (d, 1H), 7.75 (dd, 1-yl 1H), 7.57 (s, 1H), 7.49 (dd, 1H), 7.44-7.33 (m, 2H), 7.27 (dd, 1H) A28 0 — imidazo- 2 3-F, 7.71 (s, 1H), 7.68 1-yl 5-Cl (s, 1H), 7.51-7.34 (m, 4H), 7.31 (d, 1H), 7.14 (s, 1H), 7.03 (s, 1H) A29 0 1,2,4- 2 3-F, 8.58 (s, 1H), 8.01 triazo- 5-Cl (s, 1H), 7.82-7.78 1-yl (m, 2H), 7.52-7.38 (m, 3H), 7.32 (d, 1H) A30 1 3-F 3-(5- 2 3-F, 8.80 (s, 1H), 7.55- difluoro- 5-Cl 7.40 (m, 2H), 7.18 methyl)- (t, 1H), 7.09 (d, isoxazole 1H), 6.84 (s, 1H), 6.75 (t, 1H) A31 1 3-F 5-(3- 2 3-F,    7.82 (s, 1H), trifluoro- 5-Cl 7.57-7.51 (m, 2H), methyl)- 7.18 (t, 1H), 7.11 isoxazole (d, 1H), 6.88 (s, 1H) A32 1 3-CN 4- 1 5-Cl 8.00 (d, 1H), 7.93 (trifluoro- (s, 1H), 7.87 (s, methyl) 1H), 7.73 (d, 1H), pyrazol- 7.67-7.55 (m, 3H), 1-yl 6.85 (d, 1H) A33 1 3-CN 4- 2 3-F, 8.03 (s, 1H), 7.87 (trifluoro- 5-Cl (s, 1H), 7.78-7.70 methyl) (m, 2H), 7.67-7.60 pyrazol- (m, 2H), 7.48 (dd, 1-yl 1H) A34 1 3-CN 4- 2 3,5- 8.03 (s, 1H), 7.87 (trifluoro- di-F (s, 1H), 7.75-7.70 methyl) (m, 2H), 7.65-7.60 pyrazol- (m, 2H), 7.30 1-yl (ddd, 1H) A35 1 3-F 2-(5- 2 3-F, 7.78 (s, 1H), 7.55- difluoro- 5-Cl 7.45 (m, 2H), 7.38 methyl)- (s, 1H), 7.20-7.10 oxazole (m, 2H), 6.68 (t, 1H) A36 1 3-OMe 4- 2 3-F, 7.78 (s, 1H), 7.72 (trifluoro- 5-Cl (s, 2H), 7.47 (t, methyl) 1H), 7.39 (dd, pyrazol- 1H), 7.00-6.91 (m, 1-yl 2H), 3.83 (s, 3H) A37 1 3-F 5-(3- 2 3-CN, 8.15 (d, 1H), 8.00 difluoro- 5-Cl (d, 1H), 7.60-7.52 methyl)- (m, 1H), 7.27-7.20 isoxazole (m, 1H), 7.15 (dd, 1H), 6.90 (d, 1H), 6.76 (t, 1H) A38 1 3-F 5-(3- 2 3-NO.sub.2, 8.41 (d, 1H), 8.20 difluoro- 5-Cl (d, 1H), 7.60-7.54 methyl)- (m, 1H), 7.24 (t, isoxazole 1H), 7.12 (d, 1H), 6.94 (d, 1H), 6.74 (t, 1H) A39 1 3-F 5-(3- 2 3-F, 5- 8.36 (d, 1H), 7.99 difluoro- SO.sub.2Me (dd, 1H), 7.59 methyl)- (td, 1H), 7.28- isoxazole 7.24 (m, 1H), 7.15 (d, 1H), 6.89 (s, 1H), 6.76 (t, 1H), 3.10 (s, 3H) A40 1 3-F 5-(3- 1 5- 8.61 (d, 1H), 8.22 difluoro- SO.sub.2Me (dd, 1H), 7.59- methyl)- 7.53 (m, 1H), 7.25- isoxazole 7.19 (m, 2H), 7.12 (d, 1H), 6.83 (d, 1H), 6.75 (t, 1H), 3.08 (s, 3H). A41 1 3-F 5-(3- 1 5-Br 8.13 (d, 1H), 7.82 difluoro- (dd, 1H), 7.51 (dt, methyl)- 1H), 7.14 (ddd, isoxazole 1H), 7.06 (td, 1H), 6.95 (d, 1H), 6.78 (s, 1H), 6.75 (t, 1H) A42 1 3-Cl 5-(3- 2 3-F, 7.83 (d, 1H), 7.53- difluoro- 5-Cl 7.40 (m, 3H), 7.21 methyl)- (dd, 1H), 6.78 (t, isoxazole 1H), 6.69 (s, 1H) A43 0 — 5-(3- 2 3-F, 8.05 (dd, 1H), 7.88 difluoro- 5-Cl (d, 1H), 7.59 (dd, methyl)- 1H), 7.56-7.50 (m, isoxazole 1H), 7.39 (dt, 1H), 7.29-7.21 (m, 1H), 6.87 (s, 1H), 6.75 (t, 1H) A44 1 3-Br 5-(3- 2 3-F, 7.84 (d, 1H), 7.63 difluoro- 5-Cl (dd, 1H), 7.50- methyl)- 7.40 (m, 2H), 7.23 isoxazole (d, 1H), 6.80 (t, 1H), 6.64 (s, 1H) A45 0 — 1,2,3- 2 3-F, 7.84 (dd, 1H), 7.63 triazo- 5-Cl (d, 1H), 7.60 (s, 2-yl 2H), 7.45-7.28 (m, 4H) A46 1 3-NO.sub.2 4- 2 3-F, 7.99 (s, 1H), 7.89 (trifluoro- 5-Cl (dd, 1H), 7.84- methyl) 7.73 (m, 2H), 7.72- pyrazol- 7.60 (m, 2H), 7.49 1-yl (dd, 1H) A47 1 3-F 5-(3- 1 6-CF.sub.3 7.87 (t, 1H), 7.53- difluoro- 7.48 (m, 1H), 7.38 methyl)- (d, 1H), 7.20-7.12 isoxazole (m, 3H), 6.79 (s, 1H), 6.75 (t, 1H) A48 1 3-F 5-(3- 1 6- 7.77 (t, 1H), 7.52- difluoro- OCF.sub.2H 7.48 (m, 1H), 7.14 methyl)- (t, 1H), 7.08 (d, isoxazole 1H), 6.95 (t, 1H), 6.80 (d, 1H), 6.76 (d, 1H), 6.75 (t, 1H), 6.60 (d, 1H) A49 1 3-F 5-(3- 1 3-CN 8.23 (d, 1H), 8.03 difluoro- (d, 1H), 7.60-7.52 methyl)- (m, 1H), 7.25-7.10 isoxazole (m, 3H), 6.87 (s, 1H), 6.65 (t, 1H) A50 1 3-F 5-(3- 2 5,6- 7.62-7.55 (m, 1H), difluoro- di-F 7.54-7.49 (m, 1H), methyl)- 7.18-7.10 (m, 2H), isoxazole 6.87 (s, 1H), 6.75 (t, 1H), 6.61 (dd, 1H) A51 1 3-F 5-(3- 2 3-Cl, 8.20 (s, 1H), 8.01 difluoro- 5-CF.sub.3 (s, 1H), 7.58-7.53 methyl)- (m, 1H), 7.21 (t, isoxazole 1H), 7.14 (d, 1H), 6.90 (s, 1H), 6.78 (t, 1H) A53 1 3-F 5-(3- 1 3-F 7.86 (d, 1H), 7.54- difluoro- 7.45 (m, 2H), 7.18- methyl)- 7.08 (m, 2H), 7.05- isoxazole 7.00 (m, 1H), 6.85 (s, 1H), 6.75 (t, 1H) A54 1 3-Me 4- 2 3-F, 7.80 (s, 1H), 7.79- (trifluoro- 5-Cl 7.70 (m, 2H), 7.49- methyl) 7.34 (m, 2H), 7.24 pyrazol- (d, 1H), 7.15 (d, 1-yl 1H), 2.18 (s, 3H) A55 1 3-F 5-(3- 1 6- 7.85 (t, 1H), 7.52- difluoro- CHF.sub.2 7.45 (m, 1H), 7.36 methyl)- (d, 1H), 7.17-7.05 isoxazole (m, 3H), 6.80 (s, 1H), 6.73 (t, 1H), 6.32 (t, 1H) A56 1 3-F 5-(3- 1 4-Et 8.00 (d, 1H), 7.49- difluoro- 7.42 (m, 1H), 7.08 methyl)- (t, 1H), 7.05 (d, isoxazole 1H), 6.88-6.85 (m, 1H), 6.84 (s, 1H), 6.80 (s, 1H), 6.77 (t, 1H), 2.67 (q, 2H), 1.27 (t, 3H) A57 1 3-I 4- 1 3-F, 7.88 (dd, 1H), (trifluoro- 5-Cl 7.80 (dd, 2H), methyl) 7.72 (s, 1H), 7.40 pyrazol- (dd, 1H), 7.36- 1-yl 7.22 (m, 2H) A58 1 3-F 4- 1 3-F, 7.84 (s, 1H), 7.76 (trifluoro- 5-Cl (s, 2H), 7.53-7.45 methyl) (m, 1H), 7.41 pyrazol- (dd, 1H), 7.22- 1-yl 7.12 (m, 2H) A59 1 3-Br 4- 1 3-F, 7.81-7.70 (m, 3H), (trifluoro- 5-Cl 7.65 (d, 1H), 7.48- methyl) 7.35 (m, 2H), 7.30 pyrazol- (d, 1H) 1-yl A60 1 3-F 5-(3- 1 4-Cl 8.30 (d, 1H), 7.60- difluoro- 7.52 (m, 1H), 7.23 methyl)- (t, 1H), 7.02 (d, isoxazole 1H), 6.85-6.50 (m, 3H), 6.77 (t, 1H) A61 2 3,4- 4- 2 3-F, 7.85 (d, 1H), 7.82- di-Br (trifluoro- 5-Cl 7.78 (m, 2H), 7.72 methyl) (s, 1H), 7.41 (dd, pyrazol- 1H), 7.25 (d, 1H) 1-yl A62 1 3-F 5-(3- 1 4- 8.29 (d, 1H), 7.58- difluoro- OCF.sub.3 7.52 (m, 1H), 7.22 methyl)- (q, 1H), 7.04 (d, isoxazole 1H), 6.87-6.80 (m, 3H), 6.76 (t, 1H) A63 1 3-F 5-(3- 2 3- 7.98 (d, 1H), 7.53 difluoro- NO.sub.2, (q, 1H), 7.18 (t, methyl)- 4-Me 1H), 7.14 (d, 1H), isoxazole 6.96 (d, 1H), 6.88 (s, 1H), 6.76 (t, 1H), 2.43 (s, 3H) A64 1 3-F 5-(3- 1 5- 8.00 (d, 1H), 7.62 difluoro- OCF.sub.3 (dd, 1H), 7.55- methyl)- 7.49 (m, 1H), 7.15 isoxazole (t, 1H), 7.10-7.04 (m, 2H), 6.80 (s, 1H), 6.75 (t, 1H) A65 1 3-F 5-(3- 1 4-Me 7.98 (d, 1H), 7.48 difluoro- (q, 1H), 7.10 (t, methyl)- 1H), 7.04 (d, 1H), isoxazole 6.87-6.77 (m, 3H), 6.75 (t, 1H), 2.47 (s, 3H) A66 0 — 5-chloro- 2 3-F, 7.81 (s, 1H), 7.62 2-thienyl 5-Cl (d, 1H), 7.51 (d, 1H), 7.40-7.22 (m, 2H), 7.19-7.11 (m, 2H), 6.82 (d, 1H) A67 0 — 5-cyano- 2 3-F, 7.81 (s, 1H), 7.71 2-thienyl 5-Cl (d, 1H), 7.60-7.49 (m, 2H), 7.43 (t, 1H), 7.40-7.31 (m, 2H), 7.20 (d, 1H) A69 0 — 5-chloro- 2 3-F, 7.77 (s, 1H), 7.50 3-thienyl 5-Cl (d, 1H), 7.44 (d, 1H), 7.41-7.32 (m, 1H), 7.32-7.26 (m, 1H), 7.21 (s, 1H), 7.20-7.11 (m, 2H) A70 0 — 3-thienyl 2 3-F, 7.75 (s, 1H), 7.58 5-Cl (d, 1H), 7.45 (s, 1H), 7.41 (d, 1H), 7.36-7.21 (m, 4H), 7.20 (d, 1H) A71 0 — 4- 2 3-F, 7.81 (s, 1H), 7.68 methoxy- 5-Cl (d, 1H), 7.49 (d, 2-thienyl 1H), 7.38-7.24 (m, 2H), 7.14 (d, 1H), 7.04 (s, 1H), 6.20 (s, 1H), 3.77 (s, 3H) A72 0 — 2,5- 2 3-F, 7.74 (s, 1H), 7.44- dimethyl- 5-Cl 7.50 (m, 1H), 7.41- pyrazol- 7.30 (m, 3H), 7.25- 3-yl 7.21 (m, 1H), 5.92 (s, 1H), 3.70 (s, 3H), 2.19 (s, 3H) A73 0 — 2-methyl- 2 3-F, 7.78 (s, 1H), 7.59- 5- 5-Cl 7.51 (m, 1H), 7.45- (trifluoro- 7.36 (m, 3H), 7.30- methyl) 7.22 (m, 1H), 6.41 pyrazol- (s, 1H), 3.82 (s, 3-yl 3H) A74 0 — 5-methyl- 2 3-F, 8.45 (d, 1H), 7.87 sulfanyl- 5-Cl (d, 1H), 7.59 (d, 1,3,4- 1H), 7.52 (t, 1H), thia- 7.39 (t, 1H), 7.20 diazol-2- (d, 1H), 2.81 (s, yl 3H) A75 0 5-methyl- 0 3-F, 8.60 (d, 1H), 7.91 sulfonyl- 5-Cl (s, 1H), 7.68-7.55 1,3,4- (m, 2H), 7.42 (t, thia- 1H), 7.28-7.20 (m, diazol-2- 1H), 3.48 (s, 3H) yl A76 1 3-F 5-(3- 2 3-Me, 7.87 (d, 1H), 7.55- difluoro- 6-CN 7.50 (m, 1H), 7.20 methyl)- (t, 1H), 7.15 (d, isoxazole 1H), 6.95 (d, 1H), 6.88 (s, 1H), 6.75 (t, 1H), 2.35 (s, 3H) A77 1 3-F 5-(3- 1 5- 8.20 (d, 1H), 7.55- difluoro- CHF.sub.2 7.48 (m, 1H), 7.19- methyl)- 7.10 (m, 3H), 7.08 isoxazole (d, 1H), 6.78 (s, 1H), 6.75 (t, 1H), 6.65 (t, 1H) A78 1 3-F 5-(3- 2 4,5- 8.52 (s, 1H), 7.60- difluoro- di-CF.sub.3 7.54 (m, 1H), 7.45 methyl)- (s, 1H), 7.25 (t, isoxazole 1H), 7.12 (d, 1H), 6.85 (s, 1H), 6.77 (t, 1H) A79 1 3-F 5-(3- 1 6-CN 7.85 (t, 1H), 7.55- difluoro- 7.50 (m, 1H), 7.81 methyl)- (d, 1H), 7.25 (d, isoxazole 1H), 7.18 (t, 1H), 7.11 (d, 1H), 6.81 (s, 1H), 6.72 (t, 1H) A80 1 3-F 5-(3- 2 3-CF.sub.3, 8.02 (d, 1H), 7.55- difluoro- 6-Cl 7.50 (m, 1H), 7.18 methyl)- (t, 1H), 7.11 (d, isoxazole 1H), 7.02 (d, 1H), 6.82 (s, 1H), 6.78 (t, 1H) A81 0 — 4- 2 3-F, 7.93 (d, 1H), 7.89 (trifluoro- 5-Cl (s, 1H), 7.70 (s, methyl) 1H), 7.54 (t, 1H), triazol- 7.50-7.39 (m, 3H) 2-yl A82 0 — 4- 2 3-F, 8.33 (s, 1H), 7.81- (trifluoro- 5-Cl 7.89 (m, 2H), 7.57 methyl) (t, 1H), 7.52 (d, triazole- 1H), 7.45 (t, 1H), 1-yl 7.38 (d, 1H) A83 1 6-Br 5-(3- 2 3-F, 7.99 (dd, 1H), 7.78 difluoro- 5-Cl (dd, 1H), 7.76 (d, methyl)- 1H), 7.59 (dd, 1H), isoxazole 7.34 (t, 1H), 6.76 (s, 1H), 6.75 (t, 1H) A84 1 3-Br 5-(3- 2 3-CN, 8.11 (s, 1H), 7.72- difluoro- 5-F 7.66 (m, 2H), 7.47 methyl)- (t, 1H), 7.29 (d, isoxazole 1H), 6.74 (t, 1H), 6.70 (s, 1H) A85 1 3-Cl 5-(3- 2 3-CN, 8.11 (s, 1H), 7.72- difluoro- 5-F 7.68 (m, 1H), 7.57- methyl)- 7.48 (m, 2H), 7.28- isoxazole 7.22 (m, 1H), 6.74 (s, 1H), 6.74 (t, 1H) A86 1 3-Br 5-(3- 1 4-Cl 8.01 (d, 1H), 7.61 difluoro- (d, 1H), 7.43 (t, methyl)- 1H), 7.21 (d, 1H), isoxazole 7.01 (d, 1H), 6.88 (s, 1H), 6.77 (t, 1H), 6.57 (s, 1H) A87 1 3-Br 5-(3- 1 4-CN 8.25 (d, 1H), 7.67 difluoro- (d, 1H), 7.47 (t, methyl)- 1H), 7.25-7.18 (m, isoxazole 2H), 7.10 (s, 1H), 6.75 (t, 1H), 6.58 (s, 1H) A88 1 3-Br 5-(3- 1 5-NO.sub.2 8.98 (s, 1H), 8.46 difluoro- (d, 1H), 7.70 (d, methyl)- 1H), 7.50 (t, 1H), isoxazole 7.28-7.22 (m, 1H), 6.99 (d, 1H), 6.74 (t, 1H), 6.60 (s, 1H) A89 1 3-Br 5-(3- 2 3,5- 7.90 (s, 1H), 7.71 difluoro- di-Cl (s, 1H), 7.63 (d, methyl)- 1H), 7.44 (t, 1H), isoxazole 7.26 (d, 1H), 6.76 (t, 1H), 6.64 (s, 1H) A90 1 3-Br 5-(3- 1 5-CF.sub.3 8.36 (s, 1H), 7.88 difluoro- (d, 1H), 7.63 (d, methyl)- 1H), 7.43 (t, 1H), isoxazole 7.24 (d, 1H), 6.95 (d, 1H), 6.72 (t, 1H), 6.58 (s, 1H) A91 1 3-Cl 5-(3- 1 4-CN 8.26 (d, 1H), 7.57- difluoro- 7.45 (m, 2H), 7.21- methyl)- 7.16 (m, 2H), 7.14 isoxazole (s, 1H), 6.75 (t, 1H), 6.63 (s, 1H) A92 1 3-Cl 5-(3- 1 4-Cl 8.00 (d, 1H), 7.50 difluoro- (t, 1H), 7.43 (d, methyl)- 1H), 7.18 (d, 1H), isoxazole 7.02 (d, 1H), 6.90 (d, 1H), 6.75 (t, 1H), 6.61 (s, 1H) A93 1 6-F 5-(3- 2 3-F, 7.85-7.79 (m, 2H), difluoro- 5-Cl 7.60 (dd, 1H), 7.41 methyl)- (dt, 1H), 7.37-7.30 isoxazole (m, 1H), 6.84 (s, 1H), 6.77 (t, 1H) A94 1 6-Me 5-(3- 2 3-F, 7.85 (dd, 1H), 7.75 difluoro- 5-Cl (d, 1H), 7.56 (dd, methyl)- 1H), 7.46-7.39 (m, isoxazole 1H), 7.39-7.33 (m, 1H), 6.73 (t, 1H), 6.72 (s, 1H), 2.18 (s, 3H) A95 1 6-Cl 5-(3- 2 3-F, 7.95 (dd, 1H), 7.77 difluoro- 5-Cl (d, 1H), 7.60 (dt, methyl)- 2H), 7.40 (t, 1H), isoxazole 6.78 (s, 1H), 6.75 (t, 1H) A96 0 — 4- 2 3-F, 7.79-7.72 (m, 2H), methoxy- 5-Cl 7.60 (s, 1H), 7.45 pyrazol- (dd, 1H), 7.39-7.31 1-yl (m, 3H), 7.30-7.22 3.71 (s, 3H) A97 0 — 4- 2 3-F, 7.80 (s, 1H), 7.69 (trifluoro- 5-Cl (d, 1H), 7.61 (s, methyl) 1H), 7.52-7.48 (m, thien-2- 2H), 7.40 (t, 1H), yl 7.31 (t, 1H), 7.20 (d, 1H) A98 1 3-Br 5-(3- 1 6-F 7.74 (q, 1H), 7.60 difluoro- (d, 1H), 7.41 (t, methyl)- 1H), 7.29-7.20 (m, isoxazole 1H), 6.75 (t, 1H), 6.70 (d, 1H), 6.65- 6.55 (m, 2H) A99 1 3-Br 5-(3- 1 4-CF.sub.3 8.26 (d, 1H), 7.64 difluoro- (dd, 1H), 7.45 (t, methyl)- 1H), 7.29-7.18 (m, isoxazole 2H), 7.08 (s, 1H), 6.73 (t, 1H), 6.56 (s, 1H) A100 1 3-Br 5-(3- 1 5-Cl 8.04 (s, 1H), 7.63- difluoro- 7.57 (m, 2H), 7.41 methyl)- (t, 1H), 7.20 (d, isoxazole 1H), 6.81 (d, 1H), 6.76 (t, 1H), 6.57 (s, 1H) A101 1 3-Br 5-(3- 2 3,5- 7.85 (s, 1H), 7.58 difluoro- di-F (d, 1H), 7.38 (t, methyl)- 1H), 7.21 (t, 1H), isoxazole 6.93 (d, 1H), 6.84 (t, 1H), 6.75 (s, 1H) A102 1 3-Br 5-(3- 1 5-CN 8.39 (s, 1H), 7.90 difluoro- (d, 1H), 7.67 (d, methyl)- 1H), 7.46 (t, 1H), isoxazole 7.25 d, 1H), 6.95 (d, 1H), 6.73 (t, 1H), 6.58 (s, 1H) A103 1 3-Br 5-(3- 2 3-F, 7.93 (s, 1H), 7.67- difluoro- 5-Br 7.55 (m, 2H), 7.45 methyl)- (t, 1H), 7.27 (d, isoxazole 1H), 6.77 (t, 1H), 6.66 (s, 1H) A104 1 3-Br 5-(3- 2 3-F, 8.14 (s, 1H), 7.71- difluoro- 5-CF.sub.3 7.62 (m, 2H), 7.48 methyl)- (t, 1H), 7.29 (d, isoxazole 1H), 6.75 (t, 1H), 6.66 (s, 1H) A105 1 3-Br 5-(3- 2 3-CN, 8.18 (s, 1H), 7.91 difluoro- 5-Cl (s, 1H), 7.69 (d, methyl)- 1H), 7.47 (t, 1H), isoxazole 7.29 (d, 1H), 6.75 (t, 1H), 6.71 (s, 1H) A106 1 3-Br 5-(3- 1 5-Br 8.15 (s, 1H), 7.75 difluoro- (d, 1H), 7.60 d, methyl)- 1H), 7.41 (t, 1H), isoxazole 7.20 (d, 1H), 6.77 (d, 1H), 6.76 (t, 1H), 6.56 (s, 1H) A107 1 3-Br 5-(3- 1 3-CN 8.26 (s, 1H), 7.95 difluoro- (d, 1H), 7.70 (d, methyl)- 1H), 7.48 (t, 1H), isoxazole 7.32 (d, 1H), 7.11 (m, 1H), 6.75 (t, 1H), 6.69 (s, 1H) A108 1 3-Cl 5-(3- 1 5-NO.sub.2 8.98 (s, 1H), 8.49 difluoro- (d, 1H), 7.53 (m, methyl)- 2H), 7.24 (d, 1H), isoxazole 7.01 (d, 1H), 6.75 (t, 1H), 6.67 (s, 1H) A109 1 3-Cl 5-(3- 2 3,5- 7.90 (s, 1H), 7.73 difluoro- di-Cl (s, 1H), 7.51 (t, methyl)- 1H), 7.45 (d, 1H), isoxazole 7.20 (d, 1H), 6.75 (t, 1H), 6.68 (s, 1H) A110 1 3-Cl 5-(3- 1 5-CF.sub.3 8.35 (s, 1H), 7.89 difluoro- (dd, 1H), 7.54- methyl)- 7.42 (m, 2H), 7.20 isoxazole (d, 1H), 6.98 (d, 1H), 6.71 (t, 1H), 6.61 (s, 1H) A111 1 3-Cl 5-(3- 1 6-F 7.75 (q, 1H), 7.48 difluoro- (t, 1H), 7.42 (d, methyl)- 1H), 7.20 (d, 1H), isoxazole 6.75 (t, 1H), 6.77- 6.70 (m, 1H), 6.65- 6.58 (m, 2H) A112 1 3-Cl 5-(3- 1 4-CF.sub.3 8.26 (d, 1H), 7.52 difluoro- (t, 1H), 7.46 (dd, methyl)- 1H), 7.23-7.18 (m, isoxazole 2H), 7.11 (s, 1H), 6.74 (s, 1H), 6.60 (s, 1H) A113 1 3-Cl 5-(3- 1 5-Cl 8.05 (s, 1H), 7.66 difluoro- (d, 1H), 7.49 (t, methyl)- 1H), 7.44 (d, 1H), isoxazole 7.19 (d, 1H) 6.86 (d, 1H), 6.75 (t, 1H), 6.51 (s, 1H) A114 1 3-Cl 5-(3- 2 3,5- 7.86 (s, 1H), 7.47- difluoro- di-F 7.40 (m, 2H), 7.21 methyl)- (t, 1H), 7.90 (d, isoxazole 1H), 6.83 (t, 1H), 6.77 (s, 1H) A115 1 3-Cl 5-(3- 1 5-CN 8.38 (s, 1H), 7.91 difluoro- (d, 1H), 7.55-7.45 methyl)- (m, 2H), 7.20 (d, isoxazole 1H), 7.00 (d, 1H), 6.74 (t, 1H), 6.64 (s, 1H) A116 1 3-Cl 5-(3- 2 3-F, 7.91 (s, 1H), 7.60 difluoro- 5-Br (d, 1H), 7.52-7.42 methyl)- (m, 2H), 7.20 (d, isoxazole 1H), 6.75 (t, 1H), 6.70 (s, 1H) A117 1 3-Cl 5-(3- 2 3-F, 8.12 (s, 1H), 7.67 difluoro- 5-CF.sub.3 (d, 1H), 7.58-7.45 methyl)- (m, 2H), 7.28-7.22 isoxazole (m, 1H), 6.74 (t, 1H), 6.70 (s, 1H) A118 1 3-Cl 5-(3- 2 3-CN, 8.19 (s, 1H), 7.92 difluoro- 5-CF.sub.3 (s, 1H), 7.58-7.49 methyl)- (m, 2H), 7.29-7.21 isoxazole (m, 1H), 6.75 (s, 1H), 6.75 (t, 1H) A119 1 3-Cl 5-(3- 1 5-Br 8.14 (s, 1H), 7.77 difluoro- (d, 1H), 7.49 (t, methyl)- 1H), 7.43 (d, 1H), isoxazole 7.18 (d, 1H), 6.80 (d, 1H), 6.76 (t, 1H), 6.61 (s, 1H) A120 1 3-Cl 5-(3- 1 3-CN 8.25 (d, 1H), 7.97 difluoro- (d, 1H), 7.58-7.45 methyl)- (m, 2H), 7.30-7.23 isoxazole (m, 1H), 7.12-7.08 (m, 1H), 6.74 (t, 1H), 6.73 (s, 1H) A121 0 — 3- 2 3-F, 7.89 (s, 1H), 7.80- (trifluoro- 5-Cl 7.71 (m, 2H), 7.49- methyl) 7.42 (m, 2H), 7.40 pyrazole- (t, 1H), 7.32 (d, 1-yl 1H), 6.56 (s, 1H) A122 0 — 5- 2 3-F, 7.82 (s, 1H), 7.60- (trifluoro- 5-Cl 7.53 (m, 2H), 7.51 methyl) (d, 1H), 7.41-7.32 pyrazole- (m, 3H), 6.70 (s, 1-yl 1H) A123 0 — 3,5-bis 2 3-F, 7.84 (s, 1H), 7.61 (trifluoro- 5-Cl (t, 1H), 7.52 (d, methyl) 1H), 7.45 (d, 1H), pyrazol- 7.43-7.35 (m, 2H), 1-yl 6.96 (s, 1H) A124 1 3-F 5-(3- 2 4-Cl, 8.60 (s, 1H), 7.55- difluoro- 5- 7.50 (m, 1H), 7.20 methyl)- CO.sub.2Et (t, 1H), 7.12 (s, isoxazole 1H), 7.05 (d, 1H), 6.80 (d, 1H), 6.75 (t, 1H), 4.37 (q, 2H), 1.38 (t, 3H) A126 0 — 5-(3- 2 3-F, 8.20 (d, 1H), 7.75 methyl- 5-Cl (s, 1H), 7.66 (t, 1,2,4- 1H), 7.53 (dd, 1H), oxadia- 7.44 (t, 1H), 7.30 zole) (d, 1H), 2.38 (s, 3H) A128 0 — 3-(5- 2 3-F, 8.16 (d, 1H), 7.74 methyl- 5-Cl (s, 1H), 7.56 (t, 1,2,4- 1H), 7.50 (d, 1H), oxadia- 7.42 (t, 1H), 7.30 zole) (d, 1H), 2.55 (s, 3H) A129 0 — 2-(4- 2 3-F, 8.35 (d, 1H), 7.80 methyl- 5-Cl (s, 1H), 7.53 (dd, thiazole) 1H), 7.41 (t, 1H), 7.35 (t, 1H), 7.18 (d, 1H), 6.87 (s, 1H), 2.46 (s, 3H) A130 0 — 2-(5- 2 3-F, 8.12 (d, 1H), 7.75 methyl- 5-Cl (s, 1H), 7.60 (t, 1,2,4- 1H), 7.55 (dd, 1H), oxadia- 7.42 (t, 1H), 7.31 zole) (d, 1H), 2.49 (s, 3H) A131 0 — 4-(5- 2 3-F, 7.76 (d, 1H), 7.62 methyl- 5-Cl (d, 1H), 7.55 (t, thiadia- 1H), 7.41 (t, 1H), zole) 7.37 (dd, 1H), 7.31 (d, 1H), 2.58 (s, 3H) A132 0 — 2-(1,3,4- 2 3-F, 8.40 (s, 1H), 8.17 oxadia- 5-Cl (d, 1H), 7.75 (s, zole) 1H), 7.62 (t, 1H), 7.55 (dd, 1H), 7.44 (t, 1H), 7.31 (d, 1H) A137 1 3-F 5-(3- 2 3- 8.25 (d, 1H), 7.55- difluoro- CO.sub.2Et, 7.50 (m, 1H), 7.18 methyl)- 6-Cl (t, 1H), 7.12 (d, isoxazole 1H), 6.97 (d, 1H), 6.81 (s, 1H), 6.75 (t, 1H), 4.38 (q, 2H), 1.40 (t, 3H) A142 0 — 2-(5- 2 3-F, 8.52 (d, 1H), 7.99 difluoro- 5-Cl (s, 1H), 7.61 (d, methyl- 1H), 7.58-7.51 (m, sulfanyl)- 1H), 7.45-7.37 (m, 1,3,4- 1H), 7.42 (t, 1H), thiadia- 7.22 (d, 1H) zole A143 0 — 3- 2 3-F, 8.86 (br, 1H), 7.81 methyl- 5-Cl (s, 1H), 7.65-7.58 imidazo- (m, 1H), 7.48 (d, 4-yl 1H), 7.42-7.37 (m, 2H), 7.23 (t, 2H), 3.80 (s, 3H) A144 0 — 2- 2 3-F, 7.98 (d, 1H), 7.29 methyl- 5-Cl (s, 1H), 7.46 (dd, pyrazol- 1H), 7.35-7.24 (m, 3-yl 3H), 7.17 (d, 1H), 6.55 (s, 1H), 3.90 (s, 3H) A145 0 — 5-iso- 2 3-F, 8.42 (s, 1H), 7.82- thiazole 5-Cl 7.75 (m, 2H), 7.58- 7.51 (m, 2H), 7.45 (t, 1H), 7.36 (t, 1H), 7.25 (d, 1H) A146 0 — 5- 2 3-F, 8.73 (s, 1H), 8.12 thiazole 5-Cl (s, 1H), 7.80 (s, 1H), 7.69 (d, 1H), 7.49 (d, 1H), 7.42 (t, 1H), 7.32 (t, 1H), 7.21 (d, 1H) A147 0 — 2- 2 3-F, 8.42 (d, 1H), 7.88 thiazole 5-Cl (s, 1H), 7.73 (s, 1H), 7.55 (d, 1H), 7.46 (t, 1H), 7.41- 7.32 (m, 2H), 7.21 (d, 1H) A148 0 — 3-furan 2 3-F, 7.78 (d, 2H), 7.56 5-Cl (d, 1H), 7.47 (d, 1H), 7.39 (s, 1H), 7.36-7.21 (m, 2H), 7.16 (d, 1H), 6.69 (s, 1H) A149 0 — 2-furan 2 3-F, 7.98-7.88 (m, 1H), 5-Cl 7.82 (s, 1H), 7.51 (d, 1H), 7.41 (s, 1H), 7.35-7.26 (m, 2H), 7.20-7.12 (m, 1H), 6.73 (s, 1H), 6.41 (s, 1H) A154 1 3-F 5-(3- 2 5- 8.25 (d, 1H), 7.50 difluoro- CO.sub.2Et, (q, 1H), 7.13 (t, methyl)- 6-Me 1H), 7.09 (d, 1H), isoxazole 6.84-6.78 (m, 2H), 6.75 (t, 1H), 4.37 (q, 2H), 2.61 (s, 3H), 1.37 (t, 3H) A156 1 3-F 5-(3- 2 4- 7.75 (s, 1H), 7.55- difluoro- CO.sub.2Et, 7.48 (m, 1H), 7.48 methyl)- 6-Br (s, 1H), 7.17 (t, isoxazole 1H), 7.10 (d, 1H), 6.84 (s, 1H), 6.76 (t, 1H), 4.42 (q, 2H), 1.40 (t, 3H) A158 1 3-CF.sub.3 4- 2 3-F, 7.83-7.78 (m, 2H), (trifluoro- 5-Cl 7.78-7.67 (m, 3H), methyl) 7.60 (dd, 1H), 7.41 pyrazol- (dd, 1H) 1-yl A159 1 3-Cl 4- 2 3-F, 7.81-7.71 (m, 3H), (trifluoro- 5-Cl 7.53-7.42 (m, 2H), methyl) 7.40 (dd, 1H), 7.29 pyrazol- (dd, 1H) 1-yl A160 1 3-CN 5-(3- 2 3,5- 7.81-7.71 (m, 2H), difluoro- di-F 7.66 (t, 1H), 7.55 methyl)- (dd, 1H), 7.38 isoxazole (ddd, 1H), 6.98 (s, 1H), 6.80 (t, 1H) A161 1 3-CN 5-(3- 1 5-Cl 8.03 (d, 1H), 7.78- difluoro- 7.68 (m, 2H), 7.65 methyl)- (t, 1H), 7.51 (dd, isoxazole 1H), 6.98 (d, 1H), 6.89 (s, 1H), 6.79 (t, 1H) A162 1 3-CN 5-(3- 2 3-F, 7.82 (d, 1H), 7.77 difluoro- 5-Cl (dd, 1H), 7.67 (t, methyl)- 1H), 7.59-7.54 (m, isoxazole 2H), 6.98 (s, 1H), 6.80 (t, 1H) A163 0 — 3-(5- 2 3-F, 7.97 (d, 1H), 7.82 difluoro- 5-Cl (s, 1H), 7.58-7.50 methyl)- (m, 2H), 7.38 (t, isoxazole 1H), 7.22 (d, 1H), 6.95 (s, 1H), 6.73 (t, 1H) A167 0 — pyrazol- 2 3-F, 7.86 (s, 1H), 7.82- 1-yl 5-Cl 7.71 (m, 2H), 7.60 (s, 1H), 7.42 (d, 1H), 7.40-7.32 (m, 2H), 7.32-7.22 (m, 1H), 6.31 (s, 1H) A168 0 — (4- 2 3-F, 7.90 (d, 1H), 7.85 difluoro- 5-Cl (s, 1H), 7.71 (s, methyl)- 1H), 7.52 (t, 1H), triazol- 7.49-7.37 (m, 3H), 2-yl 6.75 (t, 1H) A169 0 — (4- 2 3-F, 8.25 (s, 1H), 7.84 difluoro- 5-Cl (d, 1H), 7.80 (s, methyl)- 1H), 7.55 (t, 1H), triazol- 7.52-7.40 (m, 2H), 1-yl 7.36 (d, 1H), 6.88 (t, 1H) A170 0 — 2(5- 2 3-F, 8.10 (d, 1H), 7.65 difluoro- 5-Cl (s, 1H), 7.52 (t, methyl)- 1H), 7.45 (d, 1H), oxazole 7.32 (t, 1H), 7.25- 7.20 (m, 2H), 6.55 (t, 1H) A171 1 4-Cl thiazol- 2 3-F, 8.43 (s, 1H),7.90 2-yl 5-Cl (d, 1H), 7.83 (s, 1H), 7.55 (d, 1H), 7.43-7.37 (m, 2H), 7.16 (d, 1H) A172 1 3-F 5-(3- 2 5-Cl, 7.85 (d, 1H), 7.57- difluoro- 6-CN 7.52 (m, 1H), 7.26- methyl)- 7.18 (m, 2H), 7.10 isoxazole (d, 1H), 6.85 (d, 1H), 6.67 (t, 1H) A173 1 3-F 5-(3- 2 3-CN, 8.19 (s, 1H), 7.56- difluoro- 4-Cl 7.52 (m, 1H), 7.33 methyl)- (s, 1H), 7.21 (t, isoxazole 1H), 7.07 (d, 1H), 6.84 (d, 1H), 6.76 (t, 1H) A174 1 3-F thiazol- 2 3-F, 7.82 (s, 1H), 7.75 2-yl 5-Cl (s, 1H), 7.50-7.39 (m, 3H), 7.14 (t, 1H), 7.09 (d, 1H) A175 1 3-Br thiazol- 2 3-F, 7.84 (dd, 2H), 7.61 2-yl 5-Cl (d, 1H), 7.42 (s, 1H), 7.41-7.35 (m, 2H), 7.25-7.20 (m, 1H) A176 1 3-Cl thiazol- 2 3-F, 7.88-7.80 (m, 2H), 2-yl 5-Cl 7.48-7.41 (m, 3H), 7.38 (d, 1H), 7.21- 7.15 (m, 1H)

BIOLOGICAL EXAMPLES

[0194] Seeds of a variety of test species are sown in standard soil in pots (Lolium perenne (LOLPE), Solanum nigrum (SOLNI), Amaranthus retoflexus (AMARE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Ipomoea hederacea (IPOHE)). After cultivation for one day (pre-emergence) or after 8 days cultivation (post-emergence) under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity), the plants are sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in acetone/water (50:50) solution containing 0.5% Tween 20 (polyoxyethelyene sorbitan monolaurate, CAS RN 9005-64-5). Compounds are applied at 500 g/ha unless otherwise stated. The test plants are then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity) and watered twice daily. After 13 days for pre and post-emergence, the test is evaluated for the percentage damage caused to the plant. The biological activities are shown in the following table on a five point scale (5=81-100%; 4=61-80%; 3=41-60%; 2=21-40%; 1=0-20%).

TABLE-US-00002 TABLE B1 Post-emergence Test Rate Compound (g/ha) AMARE SOLNI SETFA LOLPE ECHCG IPOHE A1 500 5 5 5 5 5 5 A2 500 5 5 5 5 5 4 A3 500 2 3 4 1 1 1 A4 500 5 5 3 1 1 1 A6 500 4 5 5 4 5 3 A7 500 2 5 5 2 4 2 A8 500 2 5 4 1 2 1 A9 500 5 5 5 5 5 4 A10 500 5 5 5 5 5 5 A12 500 5 5 5 5 5 5 A14 1000 5 5 5 5 5 4 A15 1000 1 4 3 1 2 2 A16 1000 4 5 5 5 5 5 A17 1000 5 5 5 5 5 5 A18 250 3 3 3 2 4 2 A19 1000 5 5 5 5 5 5 A20 1000 5 5 4 4 4 5 A21 1000 4 3 4 3 4 3 A22 1000 4 4 3 2 2 3 A23 1000 5 5 5 5 5 5 A24 1000 4 4 4 3 4 3 A25 1000 5 5 5 5 4 4 A26 1000 5 5 5 3 5 3 A27 250 4 5 5 2 5 2 A28 1000 5 4 1 1 1 1 A29 1000 4 4 2 1 1 2 A30 1000 5 5 5 5 5 5 A31 1000 5 5 5 5 5 5 A32 1000 5 5 5 5 5 5 A33 1000 5 5 5 5 5 5 A34 1000 5 5 5 5 5 5 A35 1000 5 5 4 1 1 2 A36 1000 5 5 5 4 4 2 A37 1000 5 5 5 4 4 5 A38 1000 5 5 1 1 1 1 A39 1000 3 3 1 1 1 1 A40 1000 3 4 1 1 1 1 A41 1000 5 5 5 5 5 5 A42 250 5 5 5 5 4 4 A43 1000 5 5 5 5 4 4 A44 1000 5 5 5 5 5 5 A46 1000 5 5 4 3 3 2 A47 1000 3 3 1 1 1 1 A48 1000 5 5 2 1 1 2 A49 1000 5 5 2 1 3 3 A50 1000 3 5 3 1 2 1 A51 1000 4 5 1 1 1 1 A54 1000 3 5 5 4 3 1 A55 1000 5 5 2 1 1 1 A57 1000 5 5 4 1 1 2 A58 1000 5 5 5 5 4 5 A59 1000 5 5 5 4 3 5 A60 1000 4 4 2 1 1 2 A61 1000 5 5 2 1 1 2 A62 1000 4 3 3 2 3 3 A66 1000 5 5 2 1 3 2 A69 1000 3 4 3 1 4 2 A70 1000 3 4 2 1 3 1 A71 1000 4 5 2 1 1 1 A76 250 2 4 1 1 1 3 A77 250 5 5 5 2 2 1 A78 1000 3 4 1 1 1 1 A80 1000 5 5 1 1 1 1 A81 1000 5 4 4 1 4 2 A82 1000 5 5 5 5 4 5 A83 1000 5 4 4 4 4 2 A84 1000 5 5 5 5 5 5 A85 1000 5 5 5 5 5 5 A86 1000 4 4 4 4 4 4 A87 1000 4 4 5 3 3 3 A88 1000 5 4 4 3 4 2 A89 1000 5 4 5 3 4 4 A90 1000 5 4 5 4 4 4 A91 1000 4 4 4 4 4 4 A92 1000 4 4 4 4 4 4 A93 1000 5 3 5 3 4 3 A94 1000 4 4 3 2 2 1 A95 1000 4 4 4 3 3 1 A97 1000 5 4 5 3 4 4 A98 1000 4 4 5 3 4 3 A99 1000 5 4 4 3 4 2 A100 250 5 NT 5 NT 5 2 A101 1000 5 5 5 4 4 5 A102 1000 5 5 5 4 4 5 A103 1000 5 5 5 5 4 5 A104 1000 4 5 4 3 4 4 A105 1000 5 5 5 4 4 5 A106 1000 5 5 5 5 4 4 A107 1000 5 5 5 3 4 4 A108 1000 5 4 4 4 4 3 A109 1000 5 5 5 3 4 4 A110 1000 5 5 5 4 4 4 A111 1000 5 5 5 4 4 4 A112 1000 4 4 4 3 3 3 A113 1000 5 4 5 5 4 5 A114 1000 5 5 5 4 4 5 A115 1000 5 5 5 4 4 5 A116 1000 5 5 5 5 4 5 A117 1000 5 4 4 4 4 5 A118 1000 5 5 5 5 5 5 A119 1000 5 5 5 5 4 5 A120 1000 5 5 5 3 4 4 A121 1000 4 4 3 1 3 2 A159 1000 5 5 5 4 3 4 A160 1000 5 5 5 5 5 5 A161 1000 5 5 5 5 5 5 A162 1000 5 5 5 5 4 5 A163 250 5 NT 5 NT 5 3 A169 250 5 NT 5 NT 5 5 NT = Not Tested

TABLE-US-00003 TABLE B2 Pre-emergence Test Rate Compound (g/ha) AMARE SOLNI SETFA LOLPE ECHCG IPOHE A1 500 5 5 5 5 5 5 A2 500 5 4 5 4 5 2 A3 500 3 3 3 1 3 1 A4 500 3 3 2 1 2 1 A6 500 5 5 5 4 4 2 A7 500 5 5 4 1 4 1 A8 500 5 4 3 1 2 1 A9 500 5 5 5 4 5 3 A10 500 5 5 5 5 5 5 A12 500 5 5 5 5 5 5 A14 1000 5 5 5 5 5 3 A15 1000 5 4 5 3 5 1 A16 1000 5 5 5 5 5 5 A17 1000 5 5 5 5 5 5 A18 250 5 5 5 1 5 1 A19 1000 5 5 5 5 5 5 A20 1000 4 3 5 5 5 3 A21 1000 5 2 5 4 5 2 A22 1000 5 1 3 1 3 1 A23 1000 5 4 5 5 5 5 A24 1000 5 3 5 4 5 3 A25 1000 5 5 5 5 5 5 A26 1000 5 5 5 5 5 4 A27 250 5 5 4 3 5 1 A28 1000 3 1 1 1 1 1 A29 1000 5 3 4 1 1 1 A30 1000 5 5 5 5 5 5 A31 1000 5 5 5 5 5 5 A32 1000 5 5 5 4 5 5 A33 1000 5 5 5 4 5 2 A34 1000 5 5 5 5 5 5 A35 1000 3 5 5 1 5 1 A36 1000 5 5 5 3 5 5 A37 1000 5 5 5 5 5 5 A38 1000 4 1 1 1 1 1 A39 1000 5 1 1 1 1 1 A40 1000 2 1 1 1 1 1 A41 1000 5 5 5 5 5 3 A42 250 5 4 5 5 5 3 A43 1000 5 5 5 5 5 4 A44 1000 5 5 5 5 5 5 A46 1000 4 1 5 1 4 1 A47 1000 1 1 1 1 1 1 A48 1000 1 1 1 1 1 1 A49 1000 5 5 5 1 3 1 A50 1000 4 4 4 1 1 1 A51 1000 1 1 1 1 1 1 A54 1000 5 5 5 5 3 1 A55 1000 2 2 4 1 1 1 A57 1000 5 4 5 1 1 NT A58 1000 5 5 5 5 5 5 A59 1000 5 5 5 4 2 2 A60 1000 5 1 1 1 2 1 A61 1000 1 1 2 1 1 1 A62 1000 4 1 1 1 1 1 A69 1000 3 1 1 1 1 1 A70 1000 2 1 1 1 1 1 A71 1000 5 1 1 1 1 1 A77 250 5 4 5 2 2 1 A78 1000 1 1 2 1 1 1 A80 1000 2 1 1 1 1 1 A81 1000 5 3 4 1 4 2 A82 1000 5 4 5 5 5 5 A83 1000 4 1 2 1 2 1 A84 1000 5 4 5 5 5 5 A85 1000 5 5 5 5 5 5 A86 1000 4 2 5 4 5 1 A87 1000 4 3 5 4 4 1 A88 1000 5 4 5 4 5 1 A89 1000 4 2 4 2 4 3 A90 1000 4 4 5 5 5 3 A91 1000 4 3 5 4 5 4 A92 1000 4 2 5 5 1 4 A93 1000 4 4 4 3 4 3 A94 1000 4 2 2 2 3 1 A95 1000 4 1 3 1 4 1 A97 1000 4 2 4 2 3 2 A98 1000 4 3 5 3 5 1 A99 1000 5 1 4 3 4 1 A100 250 5 NT 5 NT 2 1 A101 1000 5 4 5 5 5 5 A102 1000 5 4 5 5 5 4 A103 1000 5 3 5 5 5 5 A104 1000 4 2 5 4 4 4 A105 1000 5 5 5 5 5 5 A106 1000 4 3 5 5 5 3 A107 1000 5 2 5 2 4 3 A108 1000 4 4 5 5 5 1 A109 1000 4 3 4 2 2 1 A110 1000 5 4 5 4 4 4 A111 1000 5 4 5 4 5 1 A112 1000 5 2 5 3 4 1 A113 1000 5 4 5 5 5 4 A114 1000 5 4 5 5 5 5 A115 1000 5 4 5 5 5 5 A116 1000 5 4 5 5 5 4 A117 1000 5 2 5 4 4 5 A118 1000 5 4 5 5 5 4 A119 1000 5 4 5 5 5 4 A120 1000 5 4 5 2 5 3 A121 1000 4 1 3 1 4 1 A126 250 5 NT 3 NT 4 1 A159 1000 5 5 5 5 5 2 A160 1000 5 4 5 5 5 5 A161 1000 5 4 5 5 5 5 A162 1000 5 4 5 5 5 5 A163 250 5 NT 5 NT 4 1 A169 250 5 NT 5 NT 5 5 NT = Not Tested

BIOLOGICAL EXAMPLES

[0195]

TABLE-US-00004 TABLE B3 Comparative Test TEST Compound Rate GLYMA AMARE 1 PYRIMIDINE COMPARATOR WO2015/108779 CMP 55 [00060] 500 250  90  70 100 100 A30 [00061] 500 250   0   0 100 100 2 PYRIMIDINE COMPARATOR WO2015/108779 CMP 144 [00062] 500 250  90  10 100 100 A1 [00063] 500 250   0   0 100 100 A37 [00064] 500 250   0   0 100 100 3 PYRIMIDINE COMPARATOR WO2015/108779 CMP 145 [00065] 500 250  40  10 100 100 A20 [00066] 500 250   0   0 100 100 4 PYRIMIDINE COMPARATOR WO2015/089003 CMP 58 [00067] 500 250 100  90 100 100 A33 [00068] 500 250   0   0 100 100 5 PYRIMIDINE COMPARATOR [00069] 500 250 100  90 100 100 A162 [00070] 500 250   0   0 100 100

[0196] Seeds of a variety of test species were sown in standard soil in pots. After cultivation for one day (pre-emergence) under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity), the plants were sprayed with an aqueous spray solution derived from the formulation of the technical active ingredient in 0.6 ml acetone and 45 ml formulation solution containing 10.6% Emulsogen EL (Registry number 61791-12-6), 42.2% N-methyl pyrrolidone, 42.2% dipropylene glycol monomethyl ether (CAS RN 34590-94-8) and 0.2% X-77 (CAS RN 11097-66-8). The test plants were then grown in a glasshouse under controlled conditions in a glasshouse (at 24/16° C., day/night; 14 hours light; 65% humidity) and watered twice daily. After 21 days the test was evaluated (100=total damage to plant; 0=no damage to plant).

Test Plants:

[0197] Weed species: Amaranthus retroflexus (AMARE)

Crops: Soybean (Glycine max (GLYMA))

[0198] The results demonstrate that the pyridine compounds of the present invention exhibit much reduced herbicidal damage to the crop (soybean) compared to the pyrimidine compounds of the prior art whilst weed (AMARE) control remains comparable.