HERBICIDAL THIAZOLE 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.3, R.sup.4 and n 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): ##STR00022## or an agronomically acceptable salt thereof, wherein Q is selected from the group consisting of C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6haloalkyl-C(O)—, C.sub.1-C.sub.6haloalkoxy-, C.sub.1-C.sub.6haloalkoxyC(O)— and a 5-membered aromatic heterocyclic ring which is optionally substituted by 1 or 2 R.sup.2 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; X is O or S(O).sub.p; 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; R.sup.3 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.2-C.sub.3alkenyl; R.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.2-C.sub.3alkenyl; n=0, 1 or 2; and p=0, 1 or 2.

2. A compound according to claim 1, wherein Q is C.sub.1-C.sub.6fluoroalkyl.

3. A compound according to claim 1, wherein Q is C.sub.1-C.sub.6fluoroalkyl-C(O)—.

4. A compound of Formula (I) according to claim 1, wherein Q is a 5-membered aromatic heterocyclic ring selected from the group consisting of: ##STR00023## wherein R.sup.2 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.

5. A compound of Formula (I) according to claim 4, wherein Q is selected from the group consisting of Q1, Q2 and Q5.

6. A compound of Formula (I) according to claim 4, wherein Q is Q2.

7. A compound according to claim 4, wherein n is 1 and R.sup.1 is fluorine.

8. A compound according to claim 7, wherein R.sup.1 is 3-fluoro.

9. A compound according to claim 4, wherein R.sup.3 is selected from the group consisting of hydrogen, chloro, bromo and difluoromethyl.

10. A compound according to claim 4, wherein R.sup.4 is selected from the group consisting of hydrogen, chloro, bromo, methyl, vinyl and difluoromethyl.

11. A herbicidal composition comprising a compound according to claim 4 and an agriculturally acceptable formulation adjuvant.

12. A herbicidal composition according to claim 11, further comprising at least one additional pesticide.

13. A herbicidal composition according to claim 12, wherein the additional pesticide is a herbicide or herbicide safener.

14. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 11.

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

Description

EXAMPLE 1: SYNTHESIS OF 3-(DIFLUOROMETHYL)-5-[2-[5-(DIFLUOROMETHYL)THIAZOL-2-YL]OXY-6-FLUORO-PHENYL]ISOXAZOLE (1.001)

Step 1: Synthesis of 2-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenoxy]thiazole-5-carbaldehyde

[0091] ##STR00016##

[0092] A solution of 2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenol (300 mg, 1.3 mmol), 2-chlorothiazole-5-carbaldehyde (230 mg, 1.6 mmol) and K.sub.2CO.sub.3 (900 mg, 6.4 mmol) in DMF (10 mL) was stirred at RT for 1 hour. The reaction was diluted with water and extracted with Et.sub.2O. The organic extracts were washed with water, 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 EtOAc/cyclohexane as eluent to give the desired product (385 mg, 86%) as an off-white solid.

[0093] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 9.85 (s, 1H) 7.83 (s, 1H) 7.60 (td, 1H) 7.32-7.26 (m, 2H) 6.89 (d, 1H) 6.79 (t, 1H)

Step 2: Synthesis of 3-(difluoromethyl)-5-[2-[5-(difluoromethyl)thiazol-2-yl]oxy-6-fluoro-phenyl]isoxazole (1.001)

[0094] ##STR00017##

[0095] A solution of 2-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenoxy]thiazole-5-carbaldehyde (200 mg, 0.59 mmol) and bis(2-methoxyethyl)aminosulfur trifluoride (1.2 mL, 3.3 mmol) in DCM (10 mL) was heated at 80° C. for 30 mins under microwave irradiation. The reaction was cooled and then poured into satd. aq. NaHCO.sub.3 solution and extracted with DCM. The 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 EtOAc/cyclohexane as eluent to give the desired product (180 mg, 85%) as an off-white solid.

[0096] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.60-7.55 (m, 1H), 7.40-7.20 (m, 3H), 6.88 (d, 1H), 6.81 (t, 1H), 6.75 (t, 1H)

EXAMPLE 2: SYNTHESIS OF 5-[2-(5-BROMOTHIAZOL-2-YL)OXY-6-FLUORO-PHENYL]-3-(DIFLUOROMETHYL)ISOXAZOLE (1.004)

Step 1: Synthesis of 5-[2-(5-bromothiazol-2-yl)oxy-6-fluoro-phenyl]-3-(difluoromethyl)isoxazole (1.004)

[0097] ##STR00018##

[0098] A solution of 2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenol (1.0 g, 4.4 mmol), 2,5-dibromothiazole (1.25 g, 5.15 mmol), K.sub.2CO.sub.3 (3.0 g, 21 mmol) and copper(I) iodide (250 mg, 1.3 mmol) in DMF (35 mL) were heated at 130° C. for 3 hrs. The reaction was cooled, diluted with water and extracted with Et.sub.2O. The organic extracts were washed with water, 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 EtOAc/cyclohexane as eluent to give the desired product (900 mg, 53%) as an off-white solid.

[0099] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.53 (q, 1H), 7.25 (d, 1H), 7.18 (t, 1H), 7.11 (s, 1H), 6.87 (s, 1H), 6.80 (t, 1H)

EXAMPLE 3: SYNTHESIS OF 3-(DIFLUOROMETHYL)-5-[2-FLUORO-6-(5-VINYLTHIAZOL-2-YL)OXY-PHENYL]ISOXAZOLE (1.002)

Step 1: Synthesis of 3-(difluoromethyl)-5-[2-fluoro-6-(5-vinylthiazol-2-yl)oxy-phenyl]isoxazole (1.002)

[0100] ##STR00019##

[0101] A solution of 5-[2-(5-bromothiazol-2-yl)oxy-6-fluoro-phenyl]-3-(difluoromethyl)isoxazole (100 mg, 0.26 mmol), vinyl boronic acid pinacol ester (45 mg, 0.29 mmol), CsF (80 mg, 0.53 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (10 mg, 0.012 mmol) in a mixture of 1,4-dioxane (2 mL) and water (0.5 mL) was heated at 150° C. for 30 mins under microwave irradiation. The reaction was cooled, diluted with water and extracted with Et.sub.2O. The organic extracts were washed with water, 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 EtOAc/cyclohexane as eluent to give the desired product (65 mg, 75%) as an off-white solid.

[0102] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.57-7.52 (m, 1H), 7.29 (d, 1H), 7.18 (t, 1H), 7.02 (s, 1H), 6.88 (d, 1H), 6.81 (t, 1H), 6.66 (dd, 1H), 5.37 (d, 1H), 5.19 (d, 1H)

EXAMPLE 4: SYNTHESIS OF 3-(DIFLUOROMETHYL)-5-[2-FLUORO-6-(5-METHYLTHIAZOL-2-YL)OXY-PHENYL]ISOXAZOLE (1.005)

Step 1: Synthesis of 3-(difluoromethyl)-5-[2-fluoro-6-(5-methylthiazol-2-yl)oxy-phenyl]isoxazole (1.005)

[0103] ##STR00020##

[0104] A solution of 5-[2-(5-bromothiazol-2-yl)oxy-6-fluoro-phenyl]-3-(difluoromethyl)isoxazole (100 mg, 0.26 mmol), trimethylboroxine (40 mg, 0.32 mmol), K.sub.2CO.sub.3 (180 mg, 1.30 mmol) and tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.026 mmol) in a mixture of 1,4-dioxane (2 mL), and water (0.5 mL) were heated at 150° C. for 30 mins under microwave irradiation. The reaction was cooled, diluted with water and extracted with Et.sub.2O. The organic extracts were washed with water, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure. The crude product was purified by flash chromatography on silica gel using gradient of EtOAc/cyclohexane as eluent to give the desired product (45 mg, 54%) as a pale yellow oil.

[0105] .sup.1H NMR (400 MHz, CDCl.sub.3) δ 7.54-7.50 (m, 1H), 7.25 (d, 1H), 7.14 (t, 1H), 6.87 (s, 1H), 6.84 (s, 1H), 6.81 (t, 1H), 2.37 (s, 3H)

EXAMPLE 5: SYNTHESIS OF 5-[2-(5-CHLOROTHIAZOL-2-YL)SULFANYL-6-FLUORO-PHENYL]-3-(DIFLUOROMETHYL)ISOXAZOLE (1.031)

Step 1: Synthesis of O-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenyl] N,N-dimethylcarbamothioate

[0106] To a stirred solution of KOH (0.288 g, 4.36 mmol) in water (10 mL) was added 2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenol (1.00 g, 4.36 mmol) followed by dropwise addition of a solution of N,N-dimethylcarbamothioyl chloride (0.539 g, 4.36 mmol) in THF (4 mL). The reaction was stirred at RT for 10 minutes then dilute with 2M NaOH and extracted with DCM (×2). The combined organic extracts were washed with water, dried over MgSO.sub.4 and evaporated to dryness under reduced pressure to give the desired product as a yellow solid

[0107] .sup.1H NMR (400 MHz, CDCl) δ 7.51 (td, 1H) 7.18 (ddd, 1H) 7.12-7.04 (m, 1H) 6.89 (d, 1H) 6.82 (t, 1H) 3.44 (s, 3H) 3.41 (s, 3H)

Step 2: Synthesis of S-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenyl] N,N-dimethylcarbamothioate

[0108] A solution of O-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenyl] N,N-dimethylcarbamothioate (0.95 g, 3.0 mmol) in DMA (2 mL) was heated at 220° C. for 90 minutes under microwave irradiation. The reaction was allowed to cool to RT, diluted with water and extracted with Et.sub.2O. The organic phase was 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/cyclohexane as eluent to give the desired product (0.58 g, 61%).

[0109] .sup.1H NMR (400 MHz, CDCl) δ 7.55-7.45 (m, 2H), 7.32-7.23 (m, 1H), 6.83 (t, 1H), 6.72 (s, 1H), 3.00 (br, 6H)

Step 3: Synthesis of 5-[2-(5-chlorothiazol-2-yl)sulfanyl-6-fluoro-phenyl]-3-(difluoromethyl)isoxazole (B031)

[0110] To a stirred solution of S-[2-[3-(difluoromethyl)isoxazol-5-yl]-3-fluoro-phenyl] N,N-dimethylcarbamothioate (0.15 g, 0.47 mmol) in tetrahydrofuran (2.4 mL) were added KOH (0.06 g, 1.0 mmol) and MeOH (1.2 mL) and the reaction stirred at room temperature overnight. To the solution was then added 2-bromo-5-chloro-thiazole (0.19 g, 0.95 mmol) and the reaction heated to 60° C. for 6 hours. The reaction was allowed to cool to RT, diluted with water and extracted with EtOAc. The organic phase was 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/cyclohexane as eluent to give the desired product (46 mg, 27%).

[0111] Purified by column chromatography. Fractions 8-9 were combined and concentrated to provide:

[0112] .sup.1H NMR (400 MHz, CDCl) δ 7.55 (s, 1H), 7.54-7.47 (m, 1H), 7.46-7.40 (m, 1H), 7.29-7.21 (m, 1H), 6.82 (t, 1H), 6.78 (s, 1H)

TABLE-US-00001 TABLE 1 Examples of herbicidal compounds of the present invention. (I) [00021] .sup.1H NMR (400 MHz, CMP n R.sup.1 Q X R.sup.3 R.sup.4 CDCl.sub.3 unless stated) 1.001 1 3-F 5-(3-difluoro- O H CF.sub.2H 7.60-7.55 (m, 1H), methyl)- 7.40-7.20 (m, 3H), isoxazole 6.88 (d, 1H), 6.81 (t, 1H), 6.75 (t, 1H) 1.002 1 3-F 5-(3-difluoro- O H vinyl 7.57-7.52 (m, 1H), methyl)- 7.29 (d, 1H), 7.18 (t, isoxazole 1H), 7.02 (s, 1H), 6.88 (d, 1H), 6.81 (t, 1H), 6.66 (dd, 1H), 5.37 (d, 1H), 5.19 (d, 1H) 1.003 1 3-F 5-(3-difluoro- O H H 7.56-7.52 (m, 1H), methyl)- 7.29 (d, 1H), 7.20- isoxazole 7.15 (m, 2H), 6.92- 6.87 (m, 2H), 6.80 (t, 1H) 1.004 1 3-F 5-(3-difluoro- O H Br 7.53 (q, 1H), 7.25 (d, methyl)- 1H), 7.18 (t, 1H), isoxazole 7.11 (s, 1H), 6.87 (s, 1H), 6.80 (t, 1H) 1.005 1 3-F 5-(3-difluoro- O H CH.sub.3 7.54-7.50 (m, 1H), methyl)- 7.25 (d, 1H), 7.14 (t, isoxazole 1H), 6.87 (s, 1H), 6.84 (s, 1H), 6.81 (t, 1H), 2.37 (s, 3H) 1.006 1 3-F 5-(3-difluoro- O H Cl 7.58-7.51 (m, 1H), methyl)- 7.28 (d, 1H), 7.19 (t, isoxazole 1H), 7.01 (s, 1H), 6.87 (s, 1H), 6.81 (t, 1H) 1.007 1 3-F 5-(3-difluoro- O Br H 7.59-7.50 (m, 1H), methyl)- 7.29 (d, 1H), 7.20 (t, isoxazole 1H), 7.11 (s, 1H), 6.88 (s, 1H), 6.81 (t, 1H) 1.008 1 3-F 5-(3-difluoro- O Cl H 7.58-7.52 (m, 1H), methyl)- 7.30 (d, 1H), 7.21 (t, isoxazole 1H), 6.88 (d, 1H), 6.81 (t, 1H), 6.65 (s, 1H) 1.009 1 3-F 5-(3-difluoro- O CF.sub.2H H 7.59-7.51 (m, 1H), methyl)- 7.32 (d, 1H), 7.23- isoxazole 7.17 (m, 2H), 6.87 (s, 1H), 6.80 (t, 1H), 6.48 (t, 1H) 1.010 1 6-F 5-(3-difluoro- O H Cl 7.82 (td, 1H), 7.44 methyl)- (dt, 1H), 7.40-7.31 isoxazole (m, 1H), 6.99 (s, 1H), 6.84 (s, 1H), 6.80 (t, 1H) 1.011 1 6-CH.sub.3 5-(3-difluoro- O H Cl 7.87 (dd, 1H), 7.44 methyl)- (d, 1H), 7.38 (t, 1H), isoxazole 6.98 (s, 1H), 6.79 (s, 1H), 6.77 (t, 1H), 2.30 (s, 3H) 1.012 1 3-CN 5-(3-difluoro- O H Cl 7.79-7.73 (m, 2H), methyl)- 7.70-7.66 (m, 1H), isoxazole 7.02 (s, 1H), 6.98 (s, H), 6.84 (t, 1H) 1.013 1 3-CN 5-(3-difluoro- O H Br 7.81-7.63 (m, 3H), methyl)- 7.13 (s, 1H), 6.98 (s, isoxazole 1H), 6.84 (t, 1H) 1.014 1 3-CN 5-(3-difluoro- O H CF.sub.2H 7.83-7.75 (m, 2H), methyl)- 7.71 (t, 1H), 7.35 (t, isoxazole 1H), 6.99 (s, 1H), 6.83 (t, 1H), 6.77 (t, 1H) 1.015 1 3-CN 4-(trifluoro- O H Br 8.01 (s, 1H), 7.98 (s, methyl) 1H), 7.80-7.72 (m, pyrazol-1-yl 2H), 7.65 (t, H), 7.08 (s, 1H) 1.016 1 3-CN 4-(trifluoro- O H CH.sub.3 8.01 (s, 1H), 7.98 (s, methyl) 1H), 7.72 (dd, 1H), pyrazol-1-yl 7.74 (dd, 1H), 7.62 (t, 1H), 6.81 (d, 1H), 2.35 (d, 3H) 1.017 1 3-CN 4-(trifluoro- O H CF.sub.2H 8.01 (s, 1H), 7.96 (s, methyl) 1H), 7.83-7.74 (m, pyrazol-1-yl 2H), 7.68 (t, 1H), 7.29 (t, 1H), 6.73 (t, 1H) 1.018 1 3-CN 4-(trifluoro- O H Cl 8.01 (s, 1H), 7.98 (s, methyl) 1H), 7.79-7.73 (m, pyrazol-1-yl 2H), 7.65 (t, 1H), 6.98 (s, 1H) 1.019 1 3-Cl 5-(3-difluoro- O H CF.sub.2H 7.57-7.49 (m, 2H), methyl)- 7.40 (dd, 1H), 7.34 isoxazole (t, 1H), 6.81 (t, 1H), 6.74 (t, 1H), 6.72 (s, 1H) 1.020 1 3-Br 5-(3-difluoro- O H CF.sub.2H 7.68 (dd, 1H), 7.51- methyl)- 7.42 (m, 2H), 7.34 (t, isoxazole 1H), 6.80 (t, 1H), 6.74 (t, 1H), 6.67 (s, 1H) 1.021 0 — 5-(3-difluoro- O H CF.sub.2H 8.07 (dd, 1H), 7.59 methyl)- (t, 1H), 7.52-7.40 isoxazole (m, 3H), 6.87 (s, 1H), 6.80 (t, 1H), 6.76 (t, 1H) 1.022 1 3-Cl 5-(3-difluoro- O H Cl 7.57-7.44 (m, 2H), methyl)- 7.37 (d, 1H), 7.01 (s, isoxazole 1H), 6.82 (t, 1H), 6.72 (s, 1H) 1.023 1 3-Br 5-(3-difluoro- O H Cl 7.65 (dd, 1H), 7.49- methyl)- 7.39 (m, 2H), 7.01 isoxazole (s, 1H), 6.82 (t, 1H), 6.68 (s, 1H) 1.024 1 3-Br 5-(3-difluoro- O H Br 7.65 (dd, 1H), 7.49- methyl)- 7.38 (m, 2H), 7.11 isoxazole (s, 1H), 6.82 (t, 1H), 6.67 (s, 1H) 1.025 1 3-Cl 5-(3-difluoro- O H Br 7.55-7.45 (m, 2H), methyl)- 7.39-7.35 (m, 1H), isoxazole 7.11 (s, 1H), 6.82 (t, 1H), 6.72 (s, 1H) 1.026 0 H 5-(3-difluoro- O H Cl 8.06 (dd, 1H), 7.55 methyl)- (t, 1H), 7.47-7.38 isoxazole (m, 2H), 7.09 (s, 1H), 6.86 (s, 1H), 6.80 (t, 1H) 1.027 0 H 5-(3-difluoro- O H Br 8.06 (dd, 1H), 7.55 methyl)- (t, 1H), 7.47-7.39 isoxazole (m, 2H), 7.19 (s, 1H), 6.88 (s, 1H), 6.80 (t, 1H) 1.028 1 3-Br 5-(3-difluoro- O Cl Cl 7.67 (dd, 1H), 7.49- methyl)- 7.40 (m, 2H), 6.82 isoxazole (t, 1H), 6.71 (s, 1H) 1.029 1 3-F 5-(3-difluoro- O Cl Cl 7.55 (td, 1H), 7.29 methyl)- (dt, 1H), 7.21 isoxazole (ddd, 1H), 6.88 (d, 1H), 6.82 (t, 1H) 1.030 1 3-Br 5-(3-difluoro- O CF.sub.2H Cl 7.70 (dd, 1H), 7.52- methyl)- 7.41 (m, 2H), 6.82 isoxazole (t, 1H), 6.81 (t, 1H), 6.71 (s, 1H) 1.031 1 3-F 5-(3-difluoro- S Cl H 7.55 (s, 1 H), 7.54- methyl)- 7.47 (m, 1H), 7.46- isoxazole 7.40 (m, 1H), 7.29- 7.21 (m, 1H), 6.82 (t, 1H), 6.78 (s, 1H) 1.032 1 3-Cl 5-(3-difluoro- O Cl Cl 7.56-7.47 (m, 2H), methyl)- 7.39 (dd, 1H), 6.82 isoxazole (t, 1H), 6.75 (s, 1H) 1.033 1 3-F 5-(3-difluoro- O CF.sub.3 H 7.58 (td, 1H), 7.51- methyl)- 7.47 (m, 1H), 7.31 isoxazole (dt, 1H), 7.27- 7.22 (m, 1H), 6.89 (d, 1H), 6.81 (t, 1H) 1.034 1 3-Br 5-(3-difluoro- O CF.sub.3 H 7.70 (dd, 1H), 7.52- methyl)- 7.42 (m, 3H), 6.81 isoxazole (t, 1H), 6.68 (s, 1H) 1.035 1 3-F 5-(3-difluoro- O CF.sub.2H Cl 7.58 (td, 1H), 7.30 methyl)- (dt, 1H), 7.27- isoxazole 7.20 (m, 1H), 6.89 (d, 1H), 6.84 (t, 1H), 6.81 (t, 1H)

BIOLOGICAL EXAMPLES

[0113] Seeds of a variety of test species are sown in standard soil in pots Amaranthus retoflexus (AMARE), Echinochloa crus-galli (ECHCG), Setaria faberi (SETFA)). 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 250 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 Compound AMARE ECHCG SETFA 1.001 5 5 5 1.002 2 4 4 1.003 2 1 2 1.004 5 5 5 1.005 4 4 4 1.006 5 4 5 1.007 5 4 5 1.008 4 2 1 1.009 4 2 2 1.010 4 3 4 1.011 2 3 3 1.012 5 3 4 1.013 5 2 3 1.014 3 3 4 1.019 4 4 5 1.020 4 4 5 1.021 4 1 3 1.022 5 5 5 1.023 5 5 5 1.024 5 5 5 1.025 5 5 5 1.026 4 4 4 1.028 4 4 4 1.029 5 1 2 1.030 1 1 1 1.031 4 2 3 1.032 5 2 4 1.033 4 4 4 1.034 4 3 4 1.035 2 1 1

TABLE-US-00003 TABLE B2 Pre-emergence Test Compound AMARE ECHCG SETFA 1.001 5 5 5 1.002 1 4 2 1.003 5 2 2 1.004 5 4 5 1.005 5 3 4 1.006 5 5 5 1.007 5 3 5 1.008 3 1 3 1.009 4 3 5 1.010 5 4 4 1.011 4 4 1 1.012 2 4 5 1.013 2 4 4 1.014 3 5 5 1.019 2 5 5 1.020 1 5 5 1.021 3 4 4 1.022 5 5 5 1.023 5 5 5 1.024 4 5 4 1.025 5 5 5 1.026 4 4 4 1.028 2 4 4 1.029 5 1 2 1.030 1 1 1 1.031 3 2 2 1.032 5 1 1 1.033 5 4 5 1.034 4 3 5 1.035 1 1 1