Herbicidal 2-azaspiro[3-5]nonane compounds

Abstract

The present invention relates to compounds of Formula (I), wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and G are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds, in particular in crops of useful plants. ##STR00001##

Claims

1. A compound of Formula (I) ##STR00236## wherein R.sup.1 is selected from the group consisting of methyl, ethynyl, 1-propynyl, phenyl and a 5 or 6 membered heteroaryl which comprises one or two nitrogen heteroatoms, said phenyl and heteroaryl optionally substituted by one or two R.sup.15 substituents; R.sup.2 is selected from the group consisting of methyl, ethyl, methoxy and chloro; R.sup.3 is selected from the group consisting of methyl, ethyl, methoxy and chloro; R.sup.4 is selected from the group consisting of C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy-, C.sub.1-C.sub.4haloalkyl, C(O)C.sub.1-C.sub.4alkyl, C(O)C.sub.1-C.sub.4haloalkyl, S(O).sub.nC.sub.1-C.sub.6alkyl, S(O).sub.nC.sub.1-C.sub.6haloalkyl, S(O).sub.n(CH.sub.2).sub.nC.sub.3-C.sub.6cycloalkyl, S(O).sub.nC(R.sup.11)R.sup.12R.sup.13, C(O)H, C(O)(CH.sub.2).sub.nC.sub.3-C.sub.6cycloalkyl, C(O)C(R.sup.11)R.sup.12R.sup.13, C(O)C.sub.2-C.sub.4alkenyl, C(O)(CR.sup.9R.sup.10)CN, C(O)(CR.sup.9R.sup.10)(CR.sup.9R.sup.10)CN, C(O)CH.sub.2C(O)C.sub.1-C.sub.6alkyl, C(O)CH.sub.2OC(O)C.sub.1-C.sub.6alkyl, C(O)OC.sub.1-C.sub.6alkyl, C(O)OC.sub.1-C.sub.6haloalkyl, C(O)(CH.sub.2).sub.nS(O).sub.nC.sub.1-C.sub.6alkyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6alkyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.2-C.sub.6alkenyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.2-C.sub.6alkynyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6haloalkyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.3-C.sub.6cycloalkyl, C(O)OC.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6alkyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6alkyl, C(O)(CH.sub.2).sub.nNR.sup.5R.sup.6, C(O)(CH.sub.2).sub.nNR.sup.7C(O)R.sup.8, C(O)(CH.sub.2).sub.nONCR.sup.5R.sup.5, CN, S(O).sub.2NR.sup.16R.sup.17, S(O)(=NR.sup.18)R.sup.19, C(O)C(O)R.sup.20, C(O)C(R.sup.23)=NOR.sup.24, C(O)C(R.sup.23)=NNR.sup.25R.sup.26, (CH.sub.2).sub.n-phenyl, C(O)(CH.sub.2).sub.n-phenyl, S(O).sub.n(CH.sub.2).sub.n-phenyl, -heterocyclyl, C(O)(CH.sub.2).sub.n-heterocyclyl, S(O).sub.n(CH.sub.2).sub.n-heterocyclyl, wherein each heterocyclyl is a 5- or 6-membered heterocyclyl which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein said heterocyclyl or phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.5 is selected from the group consisting of hydrogen and C.sub.1-C.sub.6 alkyl; R.sup.6 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6alkyl, C.sub.2-C.sub.6alkenyl, C.sub.2-C.sub.6alkynyl, C.sub.1-C.sub.6haloalkyl, hydroxyl-, C.sub.1-C.sub.6alkoxy, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.4alkoxyC.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6haloalkyl, (CR.sup.9R.sup.10)C.sub.1-C.sub.6haloalkyl, (CR.sup.9R.sup.10)C(O)NR.sup.5R.sup.5, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; or R.sup.5 and R.sup.6 together form CH.sub.2CH.sub.2OCH.sub.2CH.sub.2; and R.sup.7 is selected from the group consisting of hydrogen and C.sub.1-C.sub.6 alkyl; R.sup.8 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.3-C.sub.6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; R.sup.9 is hydrogen or methyl; R.sup.10 is hydrogen or methyl; or R.sup.9 and R.sup.10 together form CH.sub.2CH.sub.2; and R.sup.11 is hydrogen or methyl; R.sup.12 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, hydroxyl and C.sub.1-C.sub.6 alkoxy-; R.sup.13 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, hydroxyl and C.sub.1-C.sub.6 alkoxy; or R.sup.12 and R.sup.13 together form CH.sub.2XCH.sub.2; and X is selected from the group consisting of O, S and NR.sup.14; R.sup.14 is selected from the group consisting of hydrogen, C.sub.1-C.sub.3 alkyl and C.sub.1-C.sub.3 alkoxy-; R.sup.15 is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.4 haloalkyl, cyano and halogen; R.sup.16 is hydrogen or C.sub.1-C.sub.6alkyl; and R.sup.17 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6 alkoxy-C.sub.1-C.sub.3alkyl-, C(O)C.sub.1-C.sub.6alkyl, C(O)OC.sub.1-C.sub.6alkyl and CH.sub.2CN; or R.sup.16 and R.sup.17 together form CH.sub.2CH.sub.2OCH.sub.2CH.sub.2, CH.sub.2CH.sub.2S(O).sub.2CH.sub.2CH.sub.2; R.sup.18 is hydrogen or C.sub.1-C.sub.6alkyl; R.sup.19 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.3-C.sub.6cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; R.sup.20 is selected from the group consisting of C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy-, C.sub.1-C.sub.6haloalkoxy, NR.sup.21R.sup.22, phenyl and -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; R.sup.21 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.3alkyl-, C.sub.3-C.sub.6 cycloalkyl, C.sub.1-C.sub.6haloalkyl- and C.sub.1-C.sub.6haloalkoxy-, C(O)C.sub.1-C.sub.6alkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; R.sup.22 is hydrogen or C.sub.1-C.sub.6alkyl; or R.sup.21 and R.sup.22 together form CH.sub.2CH.sub.2OCH.sub.2CH.sub.2; R.sup.23 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy- and C.sub.1-C.sub.6haloalkoxy-; R.sup.24 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkoxyC.sub.1-C.sub.3alkyl-, C.sub.3-C.sub.6cycloalkyl, CH.sub.2CN, tetrahydropyranyl-, phenyl and -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.25 is hydrogen or C.sub.1-C.sub.6 alkyl; R.sup.26 is hydrogen or C.sub.1-C.sub.6 alkyl; G is selected from the group consisting of hydrogen, (CH.sub.2).sub.nR.sup.a, C(O)R.sup.a, C(O)(CR.sup.cR.sup.d).sub.nOR.sup.b, C(O)NR.sup.aR.sup.a, S(O).sub.2R.sup.a and C.sub.1-C.sub.8alkoxy-C.sub.1-C.sub.3alkyl-; R.sup.a is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.6cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.b is selected from the group consisting of C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.6 cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.c is hydrogen or C.sub.1-C.sub.3 alkyl; R.sup.d is hydrogen or C.sub.1-C.sub.3 alkyl; and n is independently 0, 1 or 2; or an agriculturally acceptable salt thereof.

2. The compound according to claim 1, which is a compound of Formula (Ia) ##STR00237## wherein R.sup.2 is methyl or methoxy; R.sup.3 is methyl or methoxy; R.sup.4 is selected from the group consisting of C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkoxy-, C.sub.1-C.sub.4haloalkyl, C(O)C.sub.1-C.sub.4alkyl, C(O)C.sub.1-C.sub.4haloalkyl, S(O).sub.nC.sub.1-C.sub.6alkyl, S(O).sub.nC.sub.1-C.sub.6haloalkyl, S(O).sub.n(CH.sub.2).sub.nC.sub.3-C.sub.6cycloalkyl, S(O).sub.nC(R.sup.11)R.sup.12R.sup.13, C(O)H, C(O)(CH.sub.2).sub.nC.sub.3-C.sub.6cycloalkyl, C(O)C(R.sup.11)R.sup.12R.sup.13, C(O)C.sub.2-C.sub.4alkenyl, C(O)(CR.sup.9R.sup.10)CN, C(O)OC.sub.1-C.sub.6alkyl, C(O)OC.sub.1-C.sub.6haloalkyl, C(O)(CH.sub.2).sub.nS(O).sub.nC.sub.1-C.sub.6alkyl, C(O)C.sub.1-C.sub.3alkoxyC.sub.1-C.sub.6alkyl, C(O)NR.sup.5R.sup.6, C(O)(CH.sub.2).sub.nNR.sup.7C(O)R.sup.8, CN, (CH.sub.2).sub.n-phenyl, C(O)(CH.sub.2).sub.n-phenyl, S(O).sub.n(CH.sub.2).sub.n-phenyl, -heterocyclyl, C(O)(CH.sub.2).sub.n-heterocyclyl, S(O).sub.n(CH.sub.2).sub.n-heterocyclyl, wherein each heterocyclyl is a 5- or 6-membered heterocyclyl which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein said heterocyclyl or phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.5 is selected from the group consisting of hydrogen and C.sub.1-C.sub.6 alkyl; R.sup.6 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.3-C.sub.6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; or R.sup.5 and R.sup.6 together form CH.sub.2CH.sub.2OCH.sub.2CH.sub.2; and R.sup.7 is selected from the group consisting of hydrogen and C.sub.1-C.sub.6 alkyl; R.sup.8 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 alkoxy, C.sub.3-C.sub.6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 haloalkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.3 alkenyl, C.sub.2-C.sub.3 alkynyl, halogen, cyano and nitro; R.sup.9 is hydrogen or methyl; R.sup.10 is hydrogen or methyl; or R.sup.9 and R.sup.10 together form CH.sub.2CH.sub.2; and R.sup.11 is hydrogen or methyl; R.sup.12 and R.sup.13 together form CH.sub.2XCH.sub.2; X is selected from the group consisting of O, S and NR.sup.14; R.sup.14 is selected from the group consisting of hydrogen, C.sub.1-C.sub.3alkyl and C.sub.1-C.sub.3 alkoxy-; G is selected from the group consisting of hydrogen, (CH.sub.2).sub.nR.sup.a, C(O)R.sup.a, C(O)(CR.sup.cR.sup.d).sub.nOR.sup.b, C(O)NR.sup.aR.sup.a, S(O).sub.2R.sup.a and C.sub.1-C.sub.8alkoxy-C.sub.1-C.sub.3alkyl-; R.sup.a is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.6cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.b is selected from the group consisting of C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.6 cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.2-C.sub.3alkenyl, C.sub.2-C.sub.3alkynyl, halogen, cyano and nitro; R.sup.c is hydrogen or C.sub.1-C.sub.3 alkyl; R.sup.d is hydrogen or C.sub.1-C.sub.3 alkyl; and n is independently 0, 1 or 2; or an agriculturally acceptable salt thereof.

3. The compound according to claim 1, wherein R.sup.2 is methyl.

4. The compound according to claim 1, wherein R.sup.3 is methyl.

5. The compound according to claim 1, wherein R.sup.3 is methoxy.

6. The compound according to claim 1, wherein R.sup.4 is C(O)OC.sub.1-C.sub.6alkyl.

7. The compound according to claim 1, wherein R.sup.4 is C(O)NR.sup.5R.sup.6.

8. The compound according to claim 1, wherein G is hydrogen.

9. The compound according to claim 1, wherein G is C(O)C.sub.1-C.sub.6alkyl.

10. The compound according to claim 1, wherein G is C(O)OC.sub.1-C.sub.6alkyl.

11. A herbicidal composition comprising a compound of Formula (I) according to claim 1 and an agriculturally acceptable formulation adjuvant.

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

13. The herbicidal composition according to claim 12, wherein the pesticide is an 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.

Description

EXAMPLE 1: SYNTHESIS OF 2-ACETYL-7-(2,6-DIMETHYL-4-PROP-1-YNYL-PHENYL)-2-AZASPIRO[3.5]NONANE-6,8-DIONE (COMPOUND 1.001)

Step 1: Synthesis of tert-butyl 3-acetonylideneazetidine-1-carboxylate

(1) ##STR00015##

(2) tert-butyl 3-oxoazetidine-1-carboxylate (15.0 g, 87.6 mmol) and 1-(triphenyl-lambda5-phosphanylidene)propan-2-one (27.9 g, 87.6 mmol) were dissolved in anhydrous toluene (240 mL) and heated at 70 C. for 2 h. The reaction mixture was allowed to cool to RT, then concentrated in vacuo. The crude material was purified by flash column chromatography, eluting with 0-20% EtOAc in hexane to obtain tert-butyl 3-acetonylideneazetidine-1-carboxylate as a colourless oil (18.4 g, 99% yield).

(3) 1HNMR (CDCl3, 400 MHz): 6.14 (s, 1H), 4.85-4.82 (m, 2H), 4.59 (s, 2H), 2.19 (s, 3H), 1.45 (s, 9H).

Step 2: Synthesis of O2-tert-butyl O5-ethyl 6,8-dioxo-2-azaspiro[3.5]nonane-2,5-dicarboxylate

(4) ##STR00016##

(5) To a stirred solution of tert-butyl 3-acetonylideneazetidine-1-carboxylate (18.4 g, 87.1 mmol) in anhydrous ethanol (120 mL) was added diethyl propanedioate (13.3 mL, 87.1 mmol) at RT followed by drop wise addition of sodium ethoxide (21.0%, 42.3 mL, 113 mmol). The reaction mixture was stirred at RT for 3 h and then heated to reflux for 2 h. The reaction was allowed to cool to RT, and then concentrated in vacuo. The reaction mixture was diluted with water and washed with ethyl acetate. The aqueous layer was then acidified with 10% aq. citric acid and extracted with DCM (3). The combined organics were washed with brine, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo to obtain O2-tert-butyl O5-ethyl 6,8-dioxo-2-azaspiro[3.5]nonane-2,5-dicarboxylate as a brown gum which was used in the next step without further purification.

Step 3: Synthesis of tert-butyl 6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate

(6) ##STR00017##

(7) Crude O2-tert-butyl O5-ethyl 6,8-dioxo-2-azaspiro[3.5]nonane-2,5-dicarboxylate from step 2 (15.6 g, 47.9 mmol) was dissolved in ethanol (48 ml) and aqueous NaOH (12M, 84 mL) was added at RT. The reaction was stirred for 2 days at RT. Ethanol was removed in vacuo and the reaction mixture was acidified with 10% citric acid to PH-3 and saturated with brine. The mixture was then extracted with ethyl acetate (3). The combined organics were dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was triturated with pentane and diethyl ether to give tert-butyl 6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate as a brown solid (6 g, 49% yield over 2 steps).

(8) 1H NMR (400 MHz, MeOD) =3.67 (s, 4H), 2.63 (s, 4H), 1.43 (s, 9H).

Step 4: Synthesis of tert-butyl 7-(4-bromo-2,6-dimethyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate

(9) ##STR00018##

(10) tert-butyl 6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate (3.57 g, 14.1 mmol) and DMAP (10.7 g, 88.0 mmol) were dissolved in chloroform (80 mL) and stirred for 15 minutes under nitrogen before anhydrous toluene (50 mL) was added, followed by the addition of a solution of diacetoxy-(4-bromo-2,6-dimethyl-phenyl)plumbyl] acetate (10.0 g, 17.6 mmol) in chloroform (80 mL). The reaction mixture was stirred at 80 C. for 3 h and then allowed to cool to RT. The reaction mixture was acidified with 10% citric acid solution, a white precipitate was formed, which was filtered and washed with chloroform. The layers of the filtrate were separated and the aqueous layer extracted with chloroform (2). The combined organics were washed with brine, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography, eluting with 10-50% EtOAc in hexane to obtain tert-butyl 7-(4-bromo-2,6-dimethyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2carboxylate as a white foam (3.3 g, 37% yield).

(11) 1 HNMR (MeOD, 400 MHz): 7.19 (s, 2H), 3.78 (s, 4H), 2.83 (s, 4H), 1.99 (s, 6H), 1.44 (s, 9H).

Step 5: Synthesis of tert-butyl 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate

(12) ##STR00019##

(13) tert-butyl 7-(4-bromo-2,6-dimethyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2carboxylate (3.60 g, 8.25 mmol), 2-butynoic acid (2.08 g, 24.8 mmol) and 4-diphenylphosphanylbutyl(diphenyl)phosphane (0.703 g, 1.65 mmol) were taken up in anhydrous DMSO (50 mL) and de-gassed before

(14) adding bis(triphenylphosphine)palladium(II) chloride (0.579 g, 0.825 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (7.54 g, 49.5 mmol). The reaction was then heated at 120 C. for 20 h. The reaction was allowed to cool to RT and then acidified with 10% citric acid solution and extracted with EtOAc (3). The combined organics were washed with brine solution, dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography, eluting with 10-80% EtOAc in Hexane to obtain tert-butyl 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate (2.48 g, 68% yield).

(15) 1HNMR (MeOD, 400 MHz): 7.02 (s, 2H), 3.77 (s, 4H), 2.82 (s, 4H), 2.00-1.96 (9H), 1.44 (s, 9H).

Step 6: Synthesis of 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione; hydrochloride

(16) ##STR00020##

(17) tert-butyl 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-hydroxy-6-oxo-2-azaspiro[3.5]non-7-ene-2-carboxylate (2.38 g, 6.02 mmol) was stirred for 2 h at RT in a solution of HCl in Dioxane (4.00 M, 48.0 mL, 192 mmol). The RM was concentrated in vacuo to leave a brown solid. This solid was washed with a 50% ethyl acetate/hexane mixture and then dried under reduced pressure to give 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione; hydrochloride (1.98 g, quant. yield) as an off-white solid.

(18) 1HNMR (MeOD, 400 MHz: 7.04 (s, 2H), 4.00 (s, 4H), 2.97 (s, 4H), 2.02-1.96 (9H).

Step 7: Synthesis of [2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6-oxo-2-azaspiro[3.5]non-7-en-8-yl] acetate

(19) ##STR00021##

(20) 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione; hydrochloride (342 mg, 1.03 mmol) was taken up in dichloromethane (20 mL) and acetyl chloride (0.324 g, 4.12 mmol) was added at 0 C. followed by triethylamine (1.15 mL, 8.25 mmol). The reaction was stirred at RT for 2 h before being diluted with DCM, washed with water and brine solution. The organic layer was dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was purified by flash column chromatography, eluting with 10% to 100% EtOAc in Hexane to obtain [2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6-oxo-2-azaspiro[3.5]non-7-en-8-yl] acetate (237 mg, 61% yield) as an off white foam.

(21) 1HNMR (MeOD, 400 MHz): 7.01 (s, 2H), 4.18 (d, 1H), 4.09 (d, 1H), 3.95 (d, 1H), 3.84 (d, 1H), 3.10 (s, 2H), 2.91 (s, 2H), 2.0-1.97 (9H), 1.89 (s, 6H).

Step 8: Synthesis of 2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione (Compound 1.001)

(22) ##STR00022##

(23) [2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6-oxo-2-azaspiro[3.5]non-7-en-8-yl]acetate (237 mg, 0.625 mmol) was dissolved in methanol (7 mL) and to this was added K.sub.2CO.sub.3 (0.172 g, 1.25 mmol). The reaction mixture was stirred at room temperature for 1 h before being concentrated in vacuo. The residue was acidified with 10% citric acid solution and the solid that was formed, was filtered and dried to obtain 2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione (125 mg, 59% yield) as a white solid.

(24) 1HNMR (MeOD, 400 MHz): 7.03 (s, 2H), 4.07 (s, 2H), 3.83 (s, 2H), 2.86 (s, 4H), 1.99-1.98 (9H), 1.89 (s, 3H).

EXAMPLE 2: SYNTHESIS OF [2-ACETYL-7-(2,6-DIMETHYL-4-PROP-1-YNYL-PHENYL)-6-OXO-2-AZASPIRO[3.5]NON-7-EN-8-YL] METHYL CARBONATE (COMPOUND 2.001)

(25) ##STR00023##

(26) 2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione (89 mg, 0.237 mmol) was dissolved in anhdrous DCM (2.4 mL) then triethylamine (99.8 L, 0.712 mmol) added with stirring. The reaction was cooled in a salt/ice bath to 0 C. and then methylchloroformate (44 L, 0.564 mmol) was added slowly with stirring and cooling. The reaction was then stirred at RT for 60 mins. The reaction mixture was concentrated in vacuo, partitioned between water and DCM and then the organic phase passed through a phase separating cartridge before being concentrated in vacuo. The crude material was purified by reverse-phase flash column chromatography, eluting with 55-75% acetonitrile in water to obtain 2-acetyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-6-oxo-2-azaspiro[3.5]non-7-en-8-yl] methyl carbonate (32 mg, 34.% yield) as a colourless gum.

(27) .sup.1H NMR (400 MHz, chloroform) 6 ppm 1.90 (s, 3H) 1.98 (s, 6H) 2.03 (s, 3H) 2.87 (d, J=2.08 Hz, 2H) 3.07 (s, 2H) 3.71 (s, 3H) 3.87-3.99 (m, 2H) 4.01 (d, J=8.44 Hz, 2H) 7.08 (s, 2H).

EXAMPLE 3: SYNTHESIS OF 2-BENZOYL-7-(2,6-DIMETHYL-4-PROP-1-YNYL-PHENYL)-2-AZASPIRO[3.5]NONANE-6,8-DIONE (COMPOUND 1.003)

(28) ##STR00024##

(29) 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-hydroxy-2-azaspiro[3.5]non-7-en-6-one; hydrochloride (203 mg, 0.612 mmol) was taken up in DMF (5.00 mL) and cooled in an ice/water bath to 0 C. Benzoic acid (0.0700 g, 0.573 mmol) and HATU (0.262 g, 0.688 mmol) were added followed by the addition of N,N-diethylethanamine (0.174 g, 1.72 mmol). The reaction mixture was left to stir for 1 h at RT and then diluted with water and acidified with 10% citric acid solution. The mixture was extracted with EtOAc (4) and the combined organics dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC to give 2-benzoyl-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione (74 mg, 31% yield) as a white solid.

(30) 1H NMR (400 MHz, MeOD) 5=7.67-7.65 (m, 2H), 7.52-7.44 (m, 3H), 7.02 (d, 2H), 4.21 (s, 2H), 4.03 (s, 2H), 2.86 (s, 4H), 1.99-1.94 (9H).

EXAMPLE 4: SYNTHESIS OF 2-(CYCLOPROPANECARBONYL)-7-(2,6-DIMETHYL-4-PROP-1-YNYL-PHENYL)-2-AZASPIRO[3.5]NONANE-6,8-DIONE (COMPOUND 1.008)

(31) ##STR00025##

(32) 7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-8-hydroxy-2-azaspiro[3.5]non-7-en-6-one; hydrochloride (206 mg, 0.620 mmol) was taken up in DMF (5.00 mL) and cooled in an ice/water bath to 0 C. Cyclopropanecarboxylic acid (0.050 g, 0.581 mmol) and HATU (0.265 g, 0.697 mmol) were added followed by the addition of N,N-diethylethanamine (0.176 g, 1.74 mmol). The reaction mixture was left to stir for 1 h at RT and then diluted with water and acidified with 10% citric acid solution. The mixture was extracted with EtOAc (4) and the combined organics dried over Na.sub.2SO.sub.4, filtered and concentrated in vacuo. The crude material was purified by preparative HPLC to give 2-(cyclopropanecarbonyl)-7-(2,6-dimethyl-4-prop-1-ynyl-phenyl)-2-azaspiro[3.5]nonane-6,8-dione (75 mg, 35% yield) as a white solid.

(33) 1H NMR (400 MHz, MeOD) =7.02 (s, 2H), 4.18 (s, 2H), 3.82 (s, 2H), 2.84 (s, 4H), 2.00-1.98 (9H) 1.59-1.56 (m, 1H), 0.87-0.81 (m, 4H).

EXAMPLE 4: SYNTHESIS OF 2-ACETYL-7-[4-(4-FLUOROPHENYL)-2,6-DIMETHYL-PHENYL]-2-AZASPIRO[3.5]NONANE-6,8-DIONE (COMPOUND 1.085)

Step 1: Synthesis of tert-butyl 7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate

(34) ##STR00026##

(35) To a mixture of tert-butyl 7-(4-bromo-2,6-dimethyl-phenyl)-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate (10 g, 22.92 mmol), (4-fluorophenyl)boronic acid (1.5 equiv., 34.38 mmol) and [1,1-BIS(Diphenylphosphino)[ferrocene]palladium (II) dichloride dichloromethane adduct (0.1 equiv., 2.292 mmol), 1,2-dimethoxyethane (4 mL/mmol) was added potassium phosphate (6 equiv., 137.5 mmol) and water (1 mL/mmol). The resulting mixture was heated to 100 C. overnight. The reaction was allowed to cool to RT and then quenched with 10% citric acid, extracted with EtOAc (2), washed with brine (1) and dried over Na.sub.2SO.sub.4.

(36) The crude was purified using column chromatography (30-100% EtOAc in cyclohexane) to afford the title compound as a pale yellow solid (7.0 g, 54% yield).

(37) .sup.1H NMR (400 MHz, methanol) =7.63-7.57 (m, 2H), 7.26 (s, 2H), 7.17-7.09 (m, 2H), 3.81 (s, 4H), 2.86 (s, 4H), 2.08 (s, 6H), 1.46 (s, 9H)

Step 2: Synthesis of 7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-2-azoniaspiro[3.5]nonane-6,8-dione; chloride

(38) ##STR00027##

(39) tert-butyl 7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-6,8-dioxo-2-azaspiro[3.5]nonane-2-carboxylate (5.295) was suspended in dichloromethane (39.09 mL, 0.3 M) at room temperature and then HCl (4M in Dioxane) (23 mL, 8 equiv.) was added dropwise and the resulting solution was left to stir at rt under air for 3 h. The mixture was concentrated in vacuo to give 7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-2-azoniaspiro[3.5]nonane-6,8-dione; chloride as a white solid (4.5 g, quant.)

(40) .sup.1H NMR (400 MHz, methanol) =7.63-7.56 (m, 2H), 7.28 (s, 2H), 7.14 (t, J=8.8 Hz, 2H), 4.04 (s, 4H), 3.01 (s, 4H), 2.08 (s, 6H)

Step 3: Synthesis of 2-acetyl-7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-2-azaspiro[3.5]nonane-6,8-dione

(41) ##STR00028##

(42) To a stirred solution of 7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-2-azoniaspiro[3.5]nonane-6,8-dione; chloride (100 mg, 0.1933 mmol, 75 mass %) in DCM (1.933 mL, 0.1 M), N,N-diethylethanamine (0.119 mL, 0.08609 g, 4.4 equiv.) was added followed by HOAt (0.0357 g, 1.33 equiv.) and acetic acid (B, 0.0147 mL, 0.01544 g, 1.33 equiv.) at room temperature. After 5 min, EDCl (0.05931 g, 1.6 equiv.) was added and the reaction was left to stir at room temperature under air o/n.

(43) Dil Aq citric acid was added and the resultant mixture was extracted with DCM. Combined organic extracts were dried and concentrated in vacuo.

(44) Purification via preparative HPLC gave 2-acetyl-7-[4-(4-fluorophenyl)-2,6-dimethyl-phenyl]-2-azaspiro[3.5]nonane-6,8-dione (60.48% Yield, 0.046 g) as a pale brown solid.

(45) 1H NMR (400 MHz, methanol) =7.61 (dd, J=5.5, 8.2 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J=8.7 Hz, 2H), 4.11 (s, 2H), 3.86 (s, 2H), 2.92-2.85 (m, 4H), 2.10 (s, 3H), 2.09 (s, 3H), 1.91 (s, 3H)

(46) Examples of herbicidal compounds of the present invention.

(47) TABLE-US-00001 TABLE 1 COM- POUND STRUCTURE NMR 1.001 1H NMR (400 MHz, Methanol-d4): 7.03 (s, 2H), 4.07 (s, 2H), 3.83 (s, 2H), 2.86 (s, 4H), 1.99-1.98 (9H), 1.89 (s, 3H). 1.002 0 1H NMR (400 MHz, Methanol-d4): = 6.96 (s, 2H), 3.75 (s, 4H), 3.09- 3.04 (s, 2H), 2.66 (4H), 1.98-1.96 (9H), 1.32 (t, 3H) 1.003 1H NMR (400 MHz, Methanol-d4): = 7.67-7.65 (m, 2H), 7.52-7.44 (m, 3H), 7.02 (d, 2H), 4.21 (s, 2H), 4.03 (s, 2H), 2.86 (s, 4H), 1.99-1.94 (9H) 1.004 1H NMR (400 MHz, Methanol-d4): = 8.61 (d, 1H), 8.01 (d, 1H), 7.92 (t, 1H), 7.50-7.47 (m, 1H), 7.03 (s, 2H), 4.57 (s, 2H), 4.05 (s, 2H), 2.89 (s, 4H), 2.00 (s, 9H) 1.005 1H NMR (400 MHz, Methanol-d4): = 7.03 (s, 2H), 4.12 (s, 2H), 4.00 (s, 2H), 3.87 (s, 2H), 3.37 (s, 3H), 2.85 (s, 4H), 1.98-1.97 (9H) 1.006 1H NMR (400 MHz, Methanol-d4): = 7.02 (s, 2H), 3.74 (s, 4H), 2.79 (s, 4H), 1.97 (s, 9H), 1.31 (s, 9H) 1.007 1H NMR (400 MHz, Methanol-d4): = 7.02 (s, 2H), 3.92 (s, 4H), 2.85 (s, 4H), 1.98-1.96 (9H), 1.22 (s, 9H) 1.008 1H NMR (400 MHz, Methanol-d4): = 7.02 (s, 2H), 4.18 (s, 2H), 3.82 (s, 2H), 2.84 (s, 4H), 2.00- 1.98 (9H) 1.59-1.56 (m, 1H), 0.87- 0.81 (m, 4H) 1.009 1H NMR (400 MHz, Methanol-d4): = 7.02 (s, 2H), 6.16 (t, 1H), 4.26 (s, 2H), 3.95 (s, 2H), 2.86 (s, 4H), 2.02- 1.98 (s, 9H) 1.010 1H NMR (400 MHz, Methanol-d4): = 7.02 (s, 2H), 4.30 (brs, 2H), 3.80 (brs, 2H), 2.82 (s, 4H), 1.98 (s, 9H), 1.20 (s, 9H) 1.011 1H NMR (400 MHz, Methanol-d4): = 8.66 (d, 1H), 8.18 (d, 1H), 8.01 (t, 1H), 7.64-7.61 (m, 1H), 7.00 (s, 2H), 4.13-4.03 (brs, 4H), 2.80 (s, 4H), 2.00- 1.97 (s, 9H) 1.012 0 1H NMR (400 MHz, Methanol-d4): = 6.99 (s, 2H), 3.96 (s, 2H), 3.74-3.70 (4H), 2.73 (brs, 4H), 2.01 (s, 3H), 1.90 (s, 6H) 1.013 1H NMR (400 MHz, Methanol-d4): = 6.84 (s, 1H), 6.76 (s, 1H), 4.04 (s, 2H), 3.81-3.80 (d, 2H), 3.66 (s, 3H), 2.82 (s, 4H), 1.99-1.97 (6H), 1.89- 1.88 (3H). 1.014 1H NMR (400 MHz, Methanol-d4): = 6.83 (s, 1H), 6.75 (s, 1H), 3.79-3.78 (d, 4H), 3.65 (s, 3H), 3.10-3.05 (q, 2H), 2.82 (s, 4H), 1.99-1.97 (6H), 1.32 (t, 3H). 1.015 1H NMR (400 MHz, Methanol-d4): = 7.67-7.65 (d, 2H), 7.52-7.44 (m, 3H), 6.84-6.82 (d, 1H), 6.76-6.75 (d, 1H), 4.19 (s, 2H), 4.02-4.01 (d, 2H), 3.67-3.61 (3H), 2.84 (s, 4H), 1.99- 1.94 (6H). 1.016 1H NMR (400 MHz, Methanol-d4): = 8.61 (t, 1H), 8.01-7.99 (d, 1H), 7.92 (t, 1H), 7.50-7.48 (m, 1H) 6.84 (s, 1H), 6.76 (s, 1H), 4.55-4.54 (d, 2H), 4.04-4.03 (d, 2H), 3.68-3.67 (3H), 2.84 (s, 4H), 2.02-1.97 (6H). 1.017 1H NMR (400 MHz, Methanol-d4): = 6.83 (s, 1H), 6.75 (s, 1H), 4.10-4.09 (d, 2H), 4.00-3.99 (d, 2H), 3.85- 3.84 (d, 2H), 3.65 (s, 3H), 3.37-3.36 (3H), 2.78 (s, 4H), 1.99-1.98 (6H). 1.018 1H NMR (400 MHz, Methanol-d4): = 6.83 (s, 1H), 6.76 (s, 1H), 3.73-3.72 (d, 4H), 3.65 (s, 3H), 2.77-2.76 (d, 4H), 1.99-1.98 (6H), 1.31 (s, 9H). 1.019 1H NMR (400 MHz, Methanol-d4): = 6.83 (s, 1H), 6.75 (s, 1H), 3.90 (s, 4H), 3.65 (s, 3H), 2.79 (s, 4H), 1.99- 1.97 (6H), 1.21 (s, 9H). 1.020 1H NMR (400 MHz, Methanol-d4): = 6.84 (s, 1H), 6.76 (s, 1H), 4.16 (s, 2H), 3.81-3.80 (d, 2H), 3.66 (s, 3H), 2.82 (s, 4H), 2.00-1.98 (6H), 1.60- 1.57 (m, 1H), 0.86-0.80 (m, 4H). 1.021 1H NMR (400 MHz, Methanol-d4): = 6.83 (s, 1H), 6.76 (s, 1H), 4.28 (brs, 2H), 3.79 (brs, 2H), 3.66 (s, 3H), 2.79 (s, 4H), 1.99-1.98 (6H), 1.20 (s, 9H). 1.022 0 1H NMR (400 MHz, Methanol-d4): = 8.66-8.65 (d, 1H), 8.20-8.18 (d, 1H), 8.03-8.02 (t, 1H), 7.65-7.62 (m, 1H), 6.83 (s, 1H), 6.75 (s, 1H), 4.05- 4.04 (m, 4H), 3.66 (s, 3H), 2.83 (s, 4H), 2.02-1.99 (6H). 1.023 1H NMR (400 MHz, Methanol-d4): = 6.80 (s, 1H), 6.70 (s, 1H), 4.04-4.02 (d, 2H), 3.82-3.81 (d, 2H), 3.63 (s, 3H), 2.66-2.64 (4H), 1.99-1.98 (6H), 1.024 1H NMR (400 MHz, Methanol-d4): = 6.84 (s, 1H), 6.77 (s, 1H), 6.29-6.03 (m, 1H), 4.25 (s, 2H), 3.94 (s, 2H), 3.66-3.65 (s, 3H), 2.86 (s, 4H), 1.99- 1.98 (6H). 1.025 1H NMR (400 MHz, methanol-d4) = 7.60 (dd, J = 5.3, 8.9 Hz, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.9 Hz, 2H), 4.22 (s, 2H), 3.86 (s, 2H), 2.91 (d, J = 2.2 Hz, 4H), 2.10 (s, 3H), 2.09 (s, 3H), 1.65- 1.57 (m, 1H), 0.91-0.81 (m, 4H) 1.026 1H NMR (400 MHz, methanol) = 7.64-7.57 (m, 2H), 7.27 (s, 2H), 7.17- 7.09 (m, 2H), 4.17 (s, 2H), 3.99- 3.92 (m, 2H), 3.85 (s, 2H), 3.47 (dt, J = 2.1, 11.8 Hz, 2H), 2.90 (s, 4H), 2.61 (tt, J = 4.0, 11.4 Hz, 1H), 2.10 (d, J = 5.7 Hz, 6H), 1.81-1.69 (m, 2H), 1.67- 1.58 (m, 2H) 1.027 1H NMR (400 MHz, methanol) = 8.10 (d, J = 9.2 Hz, 1H), 7.61 (dd, J = 5.4, 8.7 Hz, 2H), 7.31-7.24 (m, 3H), 7.14 (t, J = 8.8 Hz, 2H), 4.64 (s, 2H), 4.19-4.15 (m, 3H), 4.12 (s, 2H), 2.97 (s, 4H), 2.12 (s, 6H) 1.028 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 6.50 (dt, J = 3.4, 74.5 Hz, 1H), 4.44 (d, J = 2.8 Hz, 2H), 4.15 (d, J = 3.8 Hz, 2H), 3.88 (d, J = 2.1 Hz, 2H), 3.67 (d, J = 1.8 Hz, 3H), 2.85 (s, 4H), 2.00 (s, 3H), 1.98 (s, 3H) 1.029 .sup.1H NMR (400 MHz, methanol) ppm 8.74 (s, 2 H) 7.88 (s, 1 H) 7.80 (s, 1 H) 3.94 (br s, 4 H) 3.78 (s, 3 H) 2.86 (s, 4 H) 2.11 (s, 3 H) 1.19-1.25 (m, 10 H) 1.030 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.27-4.13 (m, 2H), 3.96- 3.83 (m, 3H), 3.33 (s, 3H), 2.88 (s, 4H), 1.99 (s, 3H), 1.98 (s, 6H), 1.32 (d, J = 6.7 Hz, 3H) 1.031 1H NMR (400 MHz, methanol) = 8.93 (dd, J = 0.7, 2.2 Hz, 1H), 8.18 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.7, 8.4 Hz, 1H), 7.79 (s, 2H), 4.35 (br s, 2H), 3.85 (br s, 2H), 2.90 (s, 4H), 2.14 (s, 6H), 1.22 (s, 9H) 1.032 0 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.7, 2.2 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.03 (dd, J = 0.6, 8.4 Hz, 1H), 7.78 (s, 2H), 4.11 (s, 2H), 3.86 (s, 2H), 2.91 (s, 4H), 2.13 (s, J = 3.1 Hz, 6H), 1.91 (s, 3H) 1.033 1H NMR (400 MHz, methanol) = 8.49 (d, 1H), 7.97-7.87 (m, 1H), 7.71- 7.62 (m, 1H), 7.40 (s, 2H), 4.38- 4.27 (m, 2H), 3.87-3.80 (m, 2H), 3.79 (s, 3H), 2.84 (s, 4H), 2.12 (m, 3H), 1.22 (s, 9H) 1.034 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.13 (s, 2H), 3.88 (s, 2H), 3.23 (q, J = 10.8 Hz, 2H), 2.87 (s, 4H), 1.99 (s, 3H), 1.99 (s, 3H), 1.98 (s, 3H) 1.035 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.91-7.84 (m, 1H), 7.68- 7.62 (m, 1H), 7.60 (s, 2H), 4.15 (s, 2H), 4.02 (s, 2H), 3.90 (s, 2H), 3.39 (s, 3H), 2.86 (s, 4H), 2.12 (s, 6H) 1.036 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.14-4.08 (m, 2H), 3.85 (d, J = 4.0 Hz, 2H), 3.77 (s, 3H), 3.65 (dt, J = 0.9, 6.0 Hz, 2H), 3.34 (d, J = 1.2 Hz, 3H), 2.86 (s, 4H), 2.41 (dt, J = 3.1, 6.0 Hz, 2H), 2.09 (d, J = 2.4 Hz, 3H) 1.037 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.27 (s, 2H), 7.17- 7.10 (m, 2H), 4.28-4.23 (m, 1H), 4.21-4.15 (m, 1H), 3.96-3.87 (m, 3H), 3.34 (s, 3H), 2.91 (s, 4H), 2.09 (s, 6H), 1.33 (d, J = 6.6 Hz, 3H) 1.038 1.039 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 5.14 (dqd, J = 1.6, 6.6, 48.2 Hz, 1H), 4.22 (s, 2H), 3.88 (d, J = 2.3 Hz, 2H), 3.67 (d, J = 3.5 Hz, 3H), 2.85 (br s, 4H), 2.00 (s, 3H), 1.98 (s, 3H), 1.52 (ddd, J = 1.6, 6.7, 24.5 Hz, 3H) 1.040 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.10 (s, 2H), 3.87 (s, 2H), 2.88 (s, 4H), 2.70-2.64 (m, 2H), 2.59-2.52 (m, 2H), 2.00-1.97 (m, 9H) 1.041 .sup.1H NMR (400 MHz, methanol) ppm 7.38 (t, J = 8.19 Hz, 1 H) 7.18-7.25 (m, 2 H) 7.06-7.12 (m, 1 H) 7.03 (d, J = 4.40 Hz, 2 H) 4.22 (s, 2 H) 4.03 (s, 2 H) 3.83 (s, 3 H) 2.88 (s, 4 H), 1.93- 2.03 (m, 9 H) 1.042 0 1H NMR (400 MHz, methanol) = 8.50 (d, 1H), 7.92 (dd, 1H), 7.67 (td, 1H), 7.40 (s, 2H), 4.15 (d, 2H), 4.02 (d, 2H), 3.90 (d, 2H), 3.79 (s, 3H), 3.38 (d, 3H), 2.87 (s, 4H), 2.12 (s, 3H) 1.043 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 4.21 (s, 2H), 3.85 (d, 2H), 3.81 (d, 3H), 2.89 (s, 4H), 2.14 (d, 3H), 1.61-1.59 (m, 1H), 0.94- 0.78 (m, 4H) 1.044 .sup.1H NMR (400 MHz, methanol) ppm 8.28-8.33 (m, 1 H) 8.18-8.24 (m, 1 H) 7.95 (dd, J = 7.76, 0.79 Hz, 1 H) 7.05 (s, 2 H) 4.66 (s, 2 H) 4.10 (s, 2 H) 2.93 (d, J = 1.59 Hz, 4 H) 1.97- 2.05 (m, 9 H) 1.045 1H NMR (400 MHz, Methanol) = 8.94 (d, 1 H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 6.51 (td, 1H), 4.45- 3.91 (m, 6H), 3.80 (d, 3H), 2.89 (s, 4H), 2.14 (s, 3H) 1.046 1H NMR (400 MHz, methanol) Shift = 7.68-7.58 (m, 2H), 7.15 (tt, J = 2.2, 8.8 Hz, 2H), 7.05 (d, J = 0.9 Hz, 1H), 6.97 (d, J = 1.0 Hz, 1H), 3.82 (d, J = 3.2 Hz, 4H), 3.76 (s, 3H), 3.10 (q, J = 7.4 Hz, 2H), 2.88 (s, 4H), 2.08 (s, 3H), 1.34 (t, J = 7.3 Hz, 3H) 1.047 1H NMR (400 MHz, methanol) = 7.64 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 6.18 (dt, J = 2.2, 53.3 Hz, 1H), 4.28 (s, 2H), 3.97 (s, 2H), 3.77 (d, J = 2.6 Hz, 3H), 2.90 (s, 4H), 2.09 (s, 3H) 1.048 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.12 (s, 2H), 3.99-3.91 (m, 2H), 3.81 (d, J = 3.4 Hz, 2H), 3.67 (d, J = 2.9 Hz, 3H), 3.46 (br t, J = 11.8 Hz, 2H), 2.84 (s, 4H), 2.64-2.52 (m, 1H), 2.03-1.97 (m, 6H), 1.80-1.68 (m, 2H), 1.66- 1.55 (m, 2H) 1.049 1H NMR (400 MHz, methanol) = 7.03 (s, 2H), 3.85 (s, 4H), 2.89 (s, 4H), 2.67-2.58 (m, 1H), 1.99 (s, 3H), 1.97 (s, 6H), 1.10-1.04 (m, 4H) 1.050 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.91 (dd, 1H), 7.65 (dt, 1H), 7.38 (d, 2H), 4.17-4.11 (m, 2H), 4.06 (d, 2H), 3.90-3.84 (m, 2H), 3.78 (d, 3H), 3.59-3.50 (m, 2H), 2.83- 2.71 (m, 4H), 2.13 (d, 3H), 1.26-1.18 (m, 3H) 1.051 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 4.09 (s, 2H), 3.84 (d, 2H), 3.80 (s, 3H), 2.87 (s, 4H), 2.14 (d, 3H), 1.91 (d, 3H) 1.052 0 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.87 (dd, 1H), 7.65 (td, 1H), 7.60 (s, 2H), 6.19 (t, 1H), 4.29 (s, 2H), 3.98 (s, 2H), 2.88 (s, 4H), 2.12 (d, 6H) 1.053 1H NMR (400 MHz, Methanol) = 8.97-8.92 (m, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.56 (s, 2H), 3.85-3.75 (m, 7H), 3.10 (q, 2H), 2.88 (s, 4H), 2.11 (s, 3H), 1.34 (t, 3H) 1.054 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 6.50 (t, J = 74.5 Hz, 1H), 4.44 (s, 2H), 4.17 (s, 2H), 3.90 (s, 2H), 2.88 (br s, 4H), 1.99 (s, 3H), 1.98 (s, 6H) 1.055 1H NMR (400 MHz, methanol) Shift = 8.68 (d, J = 4.6 Hz, 1H), 8.20 (d, J = 7.8 Hz, 1H), 8.03 (dt, J = 1.7, 7.8 Hz, 1H), 7.68-7.59 (m, 3H), 7.15 (t, J = 9.2 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.21-3.90 (m, 4H), 3.77 (s, 3H), 2.91 (s, 4H), 2.11 (s, 3H) 1.056 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 3.84 (s, 4H), 3.10 (q, J = 7.3 Hz, 2H), 2.91 (s, 4H), 2.08 (s, 6H), 1.34 (t, J = 7.4 Hz, 3H) 1.057 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 3.96 (br s, 4H), 2.89 (s, 4H), 2.08 (s, 6H), 1.22 (s, 9H) 1.058 1H NMR (400 MHz, methanol) ppm 7.49 (d, J = 2.08 Hz, 1 H) 7.04 (s, 2 H) 6.66 (d, J = 2.20 Hz, 1 H) 4.28 (s, 2 H) 4.09 (s, 3 H) 4.01 (s, 2 H) 2.91 (s, 4 H) 1.95-2.04 (m, 10 H) 1.059 1H NMR (400 MHz, methanol) Shift = 8.10 (dd, J = 2.7, 9.2 Hz, 1H), 7.65- 7.61 (m, 2H), 7.27 (d, J = 9.2 Hz, 1H), 7.15 (t, J = 8.9 Hz, 2H), 7.09-7.05 (m, 1H), 6.99 (s, 1H), 4.62 (s, 2H), 4.17 (s, 3H), 4.10 (br d, J = 2.9 Hz, 2H), 3.79 (s, 3H), 2.93 (s, 4H), 2.12 (s, 3H) 1.060 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 4.12 (s, 2H), 3.86 (s, 2H), 3.64 (t, J = 6.0 Hz, 2H), 3.34 (s, 3H), 2.89 (s, 4H), 2.40 (t, J = 6.0 Hz, 2H), 2.09 (s, 3H), 2.09 (s, 3H) 1.061 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.22-4.18 (m, 2H), 3.85 (d, J = 4.2 Hz, 2H), 3.77 (d, J = 2.0 Hz, 3H), 2.88 (s, 4H), 2.10 (d, J = 5.1 Hz, 3H), 1.64-1.57 (m, 1H), 0.90-0.80 (m, 4H) 1.062 0 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.25-4.18 (m, 1H), 4.17-4.11 (m, 1H), 3.96- 3.82 (m, 3H), 3.67 (s, 3H), 3.33 (d, J = 3.9 Hz, 3H), 2.84 (s, 4H), 2.01 (s, 3H), 1.99 (s, 3H), 1.32 (dd, J = 2.2, 6.7 Hz, 3H) 1.063 1.064 1H NMR (400 MHz, methanol) = 8.93 (dd, J = 0.6, 2.0 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.6, 8.4 Hz, 1H), 7.78 (s, 2H), 3.81 (s, 4H), 3.16 (q, J = 7.2 Hz, 2H), 2.88 (s, 4H), 2.13 (s, 6H), 1.10 (t, J = 7.2 Hz, 3H) 1.065 1H NMR (400 MHz, methanol) = 8.52-8.47 (m, 1H), 7.95-7.88 (m, 1H), 7.71-7.63 (m, 1H), 7.39 (s, 2H), 3.82-3.76 (m, 7H), 3.16 (q, 2H), 2.90- 2.77 (m, 4H), 2.12 (s, 3H), 1.10 (t, 3H) 1.066 1H NMR (400 MHz, methanol) = 7.91-7.86 (m, 2H), 7.80-7.74 (m, 1H), 7.73-7.67 (m, 2H), 7.01 (s, 2H), 3.65 (s, 4H), 2.58 (s, 4H), 1.98 (s, 3H), 1.92 (s, 6H) 1.067 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.87 (dd, 1H), 7.65 (td, 1H), 7.60 (s, 2H), 3.84 (s, 4H), 3.10 (q, 2H), 2.88 (s, 4H), 2.11 (s, 6H), 1.34 (t, 3H) 1.068 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 5.25-5.04 (m, 1H), 4.24 (d, J = 2.6 Hz, 2H), 3.90 (s, 2H), 2.89 (d, J = 3.1 Hz, 4H), 1.99 (s, 3H), 1.98 (s, 6H), 1.56-1.47 (m, 3H) 1.069 1H NMR (400 MHz, d6-DMSO) 9.09-9.03 (m, 1H), 8.70 (d, 1H), 8.37 (dd, 1H), 8.21 (d, 1H), 8.15- 8.02 (m, 2H), 7.73-7.69 (m, 1H), 7.56 (d, 2H), 4.10-3.63 (m, 7H), 2.88-2.61 (m, 4H), 2.12-1.97 (m, 3H) 1.070 1H NMR (400 MHz, methanol) Shift = 7.66-7.60 (m, 2H), 7.15 (tt, J = 2.0 8.7 Hz, 2H), 7.06 (d, J = 0.9 Hz, 1H), 6.97 (d, J = 1.3 Hz, 1H), 3.94 (br s, 4H), 3.76 (s, 3H), 2.86 (s, 4H), 2.09 (s, 3H), 1.23 (s, 9H) 1.071 1H NMR (400 MHz, methanol) Shift = 7.68-7.60 (m, 2H), 7.15 (tt, J = 2.2, 9.0 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.14 (s, 2H), 3.96 (td, J = 2.3, 11.6 Hz, 2H), 3.84 (d, J = 3.7 Hz, 2H), 3.77 (d, J = 3.2 Hz, 3H), 3.47 (tt, J = 2.2, 11.9 Hz, 2H), 2.86 (s, 4H), 2.66-2.56 (m, 1H), 2.10 (d, J = 6.8 Hz, 3H), 1.78 (dd, J = 4.4, 13.3 Hz, 1H), 1.72 (dd, J = 4.5, 11.9 Hz, 1H), 1.67-1.58 (m, 2H) 1.072 00 1H NMR (400 MHz, methanol) = 7.72-7.64 (m, 2H), 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.56-7.45 (m, 3H), 7.27 (br s, 1H), 7.25 (br s, 1H), 7.13 (t, J = 8.9 Hz, 2H), 4.25 (s, 2H), 4.07 (s, 2H), 2.93 (s, 4H), 2.11 (s, 3H), 2.06 (s, 3H) 1.073 01 1.074 02 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.7 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 6.50 (t, J = 74.6 Hz, 1H), 4.45 (s, 2H), 4.19 (s, 2H), 3.93 (s, 2H), 2.91 (s, 4H), 2.09 (s, 6H) 1.075 03 .sup.1H NMR (400 MHz, DMSO-d.sub.6) = 8.97 (s, 2 H) 7.80 (s, 1 H) 7.70 (s, 1 H) 3.97 (s, 2 H) 3.77 (d, J = 8.31 Hz, 2 H) 3.68-3.74 (m, 5 H) 2.76 (br d, J = 3.30 Hz, 4 H) 2.03 (s, 3 H) 1.076 04 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.07 (s, 2H), 3.85 (d, J = 3.2 Hz, 2H), 3.67 (d, J = 1.7 Hz, 3H), 2.84 (s, 4H), 2.70- 2.63 (m, 2H), 2.56 (dd, J = 3.7, 6.6 Hz, 2H), 2.00 (s, 3H), 1.99 (d, J = 3.9 Hz, 3H) 1.077 05 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.10 (s, 2H), 3.85 (d, J = 2.6 Hz, 2H), 3.67 (d, J = 1.8 Hz, 3H), 3.22 (dq, J = 2.9, 10.7 Hz, 2H), 2.84 (s, 4H), 2.00 (s, 3H), 1.99 (d, J = 3.5 Hz, 3H) 1.078 06 1H NMR (400 MHz, methanol) = 8.49 (d, 1H), 7.92 (dd, 1H), 7.66 (td, 1H), 7.39 (s, 2H), 3.79 (s, 3H), 3.78- 3.74 (m, 4H), 2.88-2.76 (m, 4H), 2.12 (s, 3H), 1.32 (s, 9H) 1.079 07 1H NMR (400 MHz, methanol) = 8.84-8.80 (m, 1H), 8.16-8.10 (m, 1H), 8.02 (d, J = 7.8 Hz, 1H), 7.72 (ddd, J = 1.1, 4.7, 7.6 Hz, 1H), 7.01 (s, 2H), 3.95 (s, 4H), 2.71 (s, 4H), 1.98 (s, 3H), 1.93 (s, 6H) 1.080 08 1H NMR (400 MHz, methanol) = 7.68 (br d, J = 7.5 Hz, 2H), 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.56-7.44 (m, 3H), 7.14 (t, J = 8.8 Hz, 2H), 7.05 (br d, J = 6.6 Hz, 1H), 6.97 (br d, J = 5.0 Hz, 1H), 4.23 (s, 2H), 4.05 (d, J = 3.2 Hz, 2H), 3.80-3.68 (m, 3H), 2.89 (s, 4H), 2.15-2.03 (m, 3H) 1.081 09 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 4.33 (s, 2H), 3.83 (s, 2H), 3.80 (s, 3H), 2.86 (s, 4H), 2.14 (s, 4H), 1.22 (s, 9H) 1.082 0 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.90-7.84 (m, 1H), 7.68- 7.62 (m, 1H), 7.60 (s, 2H), 4.22- 4.15 (m, 2H), 4.08-4.04 (m, 2H), 3.92-3.87 (m, 2H), 3.54 (q, 2H), 2.85 (s, 4H), 2.12 (s, 6H), 1.22 (t, 3H) 1.083 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (s, 1 H) 7.70 (s, 1 H) 4.06 (s, 2 H) 3.71 (d, J = 2.93 Hz, 3 H) 3.66 (br s, 2 H) 2.66-2.92 (m, 4 H) 2.04 (d, J = 5.01 Hz, 3 H) 1.52- 1.62 (m, 1 H) 0.66-0.76 (m, 4 H) 1.084 .sup.1H NMR (400 MHz, methanol) ppm 7.38 (t, J = 8.19 Hz, 1 H) 7.18-7.24 (m, 2 H) 7.06-7.11 (m, 1 H) 7.03 (d, J = 4.40 Hz, 2 H) 4.22 (s, 2 H) 4.03 (s, 2 H) 3.83 (s, 3 H) 2.88 (s, 4 H) 1.97- 2.02 (m, 6 H) 1.95 (s, 3 H) 1.085 1H NMR (400 MHz, methanol) = 7.61 (dd, J = 5.5, 8.2 Hz, 2 H), 7.27 (s, 2H), 7.13 (t, J = 8.7 hz, 2H), 4.11 (s, 2H), 3.86 (s, 2H), 2.92-2.85 (m, 4H), 2.10 (s, 3H), 2.09 (s, 3H), 1.91 (s, 3H) 1.086 1.087 1H NMR (400 MHz, methanol) = 7.64 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.26-4.21 (m, 1H), 4.16 (dd, J = 4.6, 9.7 Hz, 1H), 3.97-3.85 (m, 3H), 3.77 (s, 3H), 3.34 (d, J = 4.0 Hz, 3H), 2.87 (s, 4H), 2.10 (s, 3H), 1.33 (dd, J = 2.2, 6.7 Hz, 3H) 1.088 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.14 (s, 2H), 3.88 (d, J = 2.9 Hz, 2H), 3.77 (d, J = 1.6 Hz, 3H), 3.24 (dq, J = 3.2, 10.7 Hz, 2H), 2.87 (s, 4H), 2.09 (d, J = 3.7 Hz, 3H) 1.089 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.9 Hz, 2H), 5.15 (qd, J = 6.7, 48.4 Hz, 1H), 4.27 (d, J = 2.4 Hz, 2H), 3.93 (s, 2H), 2.92 (d, J = 3.1 Hz, 4H), 2.09 (s, 6H), 1.53 (dd, J = 6.7, 24.5 Hz, 3H) 1.090 .sup.1H NMR (400 MHz, methanol) ppm 8.74 (s, 2 H) 7.87 (s, 1 H) 7.80 (s, 1 H) 3.78 (s, 3 H) 3.76 (d, J = 2.81 Hz, 4 H) 2.82 (d, J = 2.45 Hz, 4 H) 2.12 (s, 3 H) 1.32 (s, 9 H) 1.091 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.29-4.19 (m, 3H), 3.92-3.78 (m, 4H), 3.74- 3.57 (m, 7H), 2.83 (d, J = 5.1 Hz, 4H), 2.00 (s, 3H), 1.98 (s, 3H) 1.092 0 1H NMR (400 MHz, methanol) = 8.37-8.31 (m, 1H), 7.55-7.49 (m, 1H), 7.32 (s, 1H), 6.84 (d, J = 5.5 Hz, 1H), 6.77 (d, J = 3.8 Hz, 1H), 4.23 (s, 2H), 4.03 (s, 2H), 3.65 (d, J = 21.3 Hz, 3H), 2.88 (s, 4H), 2.04-1.94 (m, 6H) 1.093 1H NMR (400 MHz, DMSO-d.sub.6) = 8.62 (d, 1H), 7.98 (dd, 1H), 7.85- 7.75 (td, 1H), 7.66 (s, 2H), 3.96 (s, 2H), 3.65 (s, 2H), 2.88-2.71 (m, 4H), 2.03 (d, 6H), 1.78 (s, 3H) 1.094 1H NMR (400 MHz, methanol) Shift = 8.92 (d, J = 1.3 Hz, 1H), 8.63 (d, J = 4.6 Hz, 1H), 8.19-8.14 (m, 1H), 8.07- 8.01 (m, 2H), 7.98-7.91 (m, 1H), 7.79 (s, 2H), 7.54-7.47 (m, 1H), 4.65- 4.56 (m, 2H), 4.11-4.08 (m, 2H), 2.93 (s, 4H), 2.16 (d, J = 5.6 Hz, 6H) 1.095 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.97 (d, J = 1.0 Hz, 1H), 4.32 (br s, 2H), 3.82 (br s, 2H), 3.76 (s, 3H), 2.85 (s, 4H), 2.09 (s, 3H), 1.22 (s, 9H) 1.096 1H NMR (400 MHz, methanol) = 8.93 (d, J = 1.5 Hz, 1H), 8.17 (dd, J = 2.2, 8.3 Hz, 1H), 8.04 (dd, J = 0.7, 8.4 Hz, 1H), 7.79 (s, 2H), 4.15 (s, 2H), 3.92 (s, 2H), 3.64 (s, 2H), 2.92 (s, 4H), 2.13 (s, 6H) 1.097 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 4.18-3.86 (m, 6H), 3.80 (m, 3H), 3.39 (d, 3H), 2.88 (s, 4H), 2.14 (s, 3H) 1.098 1H NMR (400 MHz, methanol) = 8.51-8.44 (m, 1H), 7.91-7.84 (m, 1H), 7.69-7.62 (m, 1H), 7.61 (s, 2H), 3.80 (s, 4H), 3.21-3.11 (q, 2H), 2.87 (s, 4H), 2.12 (s, 6H), 1.10 (t, 3H) 1.099 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (s, 1 H) 7.70 (s, 1 H) 3.93 (s, 2 H) 3.70 (d, J = 1.34 Hz, 3 H) 3.63 (br d, J = 2.57 Hz, 2 H) 2.65- 2.88 (m, 4 H) 2.04 (d, J = 3.30 Hz, 3 H) 1.78 (d, J = 4.89 Hz, 3 H) 1.100 .sup.1H NMR (400 MHz, methanol) ppm 7.45 (ddd, J = 8.59, 7.31, 1.71 Hz, 1 H) 7.33 (dd, J = 7.58, 1.71 Hz, 1 H) 7.10 (d, J = 8.44 Hz, 1 H) 6.99-7.06 (m, 3 H) 4.00 (s, 2 H) 3.90 (s, 3 H) 3.85 (s, 2 H) 2.87 (d, J = 6.11 Hz, 4 H) 1.99 (d, J = 2.32 Hz, 6 H) 1.90 (s, 3 H) 1.101 1H NMR (400 MHz, methanol) = 7.66-7.60 (m, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.12 (d, J = 3.8 Hz, 2H), 3.89 (d, J = 2.3 Hz, 2H), 3.76 (s, 3H), 3.64 (d, J = 4.5 Hz, 2H), 2.88 (s, 4H), 2.09 (d, J = 1.6 Hz, 3H) 1.102 0 .sup.1H NMR (400 MHz, methanol) = 7.49 (s, 1H), 7.04 (s, 2H), 4.30 (s, 2H), 3.97 (s, 3H), 3.96-3.92 (m, 2H), 2.89 (s, 4H), 1.99 (s, 3H), 1.98 (s, 6H) 1.103 1H NMR (400 MHz, methanol) Shift = 7.67-7.60 (m, 2H), 7.15 (tt, J = 3.1, 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.10 (s, 2H), 3.87 (d, J = 3.7 Hz, 2H), 3.77 (d, J = 1.8 Hz, 3H), 2.87 (s, 4H), 2.67 (t, J = 7.1 Hz, 2H), 2.61- 2.52 (m, 2H), 2.10 (d, J = 4.2 Hz, 3H) 1.104 1H NMR (400 MHz, methanol) Shift = 8.35 (t, J = 4.4 Hz, 1H), 7.69-7.59 (m, 2H), 7.54 (m, 1H), 7.33 (br s, 1H), 7.15 (tt, J = 2.7, 8.9 Hz, 2H), 7.06 (d, J = 5.9 Hz, 1H), 6.97 (d, J = 3.3 Hz, 1H), 4.26 (s, 2H), 4.06 (d, J = 2.2 hz, 2H), 3.75 (d, J = 21.5 Hz, 3H), 2.91 (s, 4H), 2.09 (d, J = 15.5 Hz, 3H) 1.105 1.106 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 8.60-8.67 (m, 1 H) 7.95- 8.01 (m, 2 H) 7.81 (s, 1 H) 7.71 (s, 1 H) 7.52-7.59 (m, 1 H) 4.44 (s, 2 H) 3.91 (s, 2 H) 3.72 (d, J = 2.81 Hz, 3 H) 2.06 (d, J = 7.58 Hz, 3 H) 1.107 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.13 (d, J = 2.8 Hz, 2H), 4.04 (d, J = 2.4 Hz, 2H), 3.85 (d, J = 3.4 Hz, 2H), 3.66 (d, J = 1.5 Hz, 3H), 3.53 (dq, J = 2.9, 7.0 Hz, 2H), 2.83 (s, 4H), 2.00 (s, 3H), 1.98 (s, 3H), 1.21 (q, J = 7.0 Hz, 3H) 1.108 .sup.1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.43 (s, 2H), 3.90 (s, 2H), 3.67 (s, 3H), 2.86 (s, 4H), 2.00 (s, 3H), 1.99 (s, 3H), 1.56 (s, 6H) 1.109 1H NMR (400 MHz, methanol) = 8.93 (dd, J = 0.7, 2.1 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.7, 8.4 Hz, 1H), 7.78 (s, 2H), 3.97 (s, 4H), 2.91 (s, 4H), 2.12 (s, 6H), 1.23 (s, 9H) 1.110 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.9, 2.2 Hz, 1H), 8.17 (dd, J = 2.1, 8.4 Hz, 1H), 8.04 (dd, J = 0.7, 8.7 Hz, 1H), 7.78 (br d, J = 2.4 Hz, 2H), 7.71-7.66 (m, 2H), 7.55- 7.46 (m, 3H), 4.26 (s, 2H), 4.07 (s, 2H), 2.99-2.90 (s, 4H), 2.20-2.08 (s, 6H) 1.111 1H NMR (400 MHz, DMSO-d.sub.6) = 8.65 (d, 1H), 8.11-8.01 (m, 1H), 7.87- 7.75 (m, 1H), 7.46 (s, 1H), 7.41 (s, 1H), 3.99-3.88 (m, 2H), 3.75-3.67 (m, 3H), 3.66-3.59 (m, 2H), 2.90- 2.66 (m, 4H), 2.07-1.98 (m, 3H), 1.83-1.72 (m, 3H) 1.112 0 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.9 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.99- 6.96 (m, 1H), 4.14 (d, J = 3.8 Hz, 2H), 4.02 (d, J = 3.2 Hz, 2H), 3.89 (d, J = 3.5 Hz, 2H), 3.77 (s, 3H), 3.39 (d, J = 3.4 Hz, 3H), 2.87 (s, 4H), 2.09 (s, 3H) 1.113 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 6.19 (td, 1H), 4.29 (s, 2H), 3.98 (s, 2H), 3.80 (d, 3H), 2.91 (s, 4H), 2.14 (s, 3H) 1.114 1H NMR (400 MHz, d6-DMSO) = 9.09 (d, 1H), 8.38 (dd, 1H), 8.23 (d, 1H), 7.58 (d, 2H), 3.97 (s, 2H), 3.77 (d, 4H), 3.72 (s, 3H), 2.85-2.68 (m, 4H), 2.04 (s, 3H) 1.115 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.04 (q, J = 3.10 Hz, 2 H) 7.02 (s, 2 H) 4.45 (s, 2 H) 3.93 (s, 2 H) 2.74-2.97 (m, 4 H) 2.02 (s, 3 H) 1.93 (s, 6 H) 1.116 1H NMR (400 MHz, methanol) Shift = 7.68-7.57 (m, 2H), 7.15 (tt, J = 3.2, 8.9 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 6.51 (dt, J = 3.5, 74.5 Hz, 1H), 4.45 (d, J = 2.7 Hz, 2H), 4.17 (d, J = 4.3 Hz, 2H), 3.91 (d, J = 2.8 Hz, 2H), 3.76 (d, J = 1.3 Hz, 3H), 2.88 (s, 4H), 2.09 (s, 3H) 1.117 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (br d, J = 6.85 Hz, 1 H) 7.64-7.72 (m, 3 H) 7.43-7.57 (m, 3 H) 4.13 (br s, 2 H) 3.88 (s, 2 H) 3.63-3.75 (m, 3 H) 2.79 (br s, 4 H) 1.97-2.08 (m, 3 H) 1.118 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.91-7.83 (m, 1H), 7.72- 7.58 (m, 5H), 7.56-7.44 (m, 3H), 4.25 (s, 2H), 4.06 (s, 2H), 2.90 (s, 4H), 2.14 (s, 3H), 2.09 (s, 3H) 1.119 1H NMR (400 MHz, methanol) = 7.92-7.85 (m, 2H), 7.81-7.74 (m, 1H), 7.73-6.67 (m, 2H), 6.82 (s, 1H), 6.74 (s, 1H), 3.67-3.59 (m, 7H), 2.54 (s, 4H), 1.99 (s, 3H), 1.92 (s, 3H) 1.120 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.6, 2.1 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.7, 8.4 Hz, 1H), 7.78 (s, 2H), 4.20 (s, 2H), 4.07 (s, 2H), 3.91 (s, 2H), 3.55 (q, J = 7.1 Hz, 2H), 2.91 (s, 4H), 2.13 (s, 6H), 1.22 (t, J = 7.0 Hz, 3H) 1.121 .sup.1H NMR (400 MHz, methanol) ppm 7.63-7.69 (m, 2 H) 6.97-706 (m, 4 H) 4.26 (s, 2 H) 4.02 (s, 2 H) 3.85 (s, 3 H) 2.89 (s, 4 H) 1.93-2.02 (m, 9 H) 1.122 0 1H NMR (400 MHz, methanol) = 8.52-8.46 (m, 1H), 7.95-7.87 (m, 1H), 7.70-7.61 (m, 1H), 7.39 (s, 2H), 4.24-4.16 (m, 2H), 3.87-3.82 (m, 2H), 3.79 (s, 3H), 2.92-2.81 (m, 4H), 2.13 (d, 3H), 1.66-1.55 (m, 1H), 0.93- 0.76 (m, 4H) 1.123 .sup.1H NMR (400 MHz, methanol) ppm 8.79 (d, J = 1.71 Hz, 1 H) 7.04 (s, 2 H) 6.81 (d, J = 1.59 Hz, 1 H) 4.44 (s, 2 H) 4.05 (s, 2 H) 2.91 (s, 4 H) 2.00 (d, J = 2.32 Hz, 9 H) 1.124 1H NMR (400 MHz, methanol) = 8.49 (d, 1H), 7.95-7.88 (m, 1H), 7.72- 7.62 (m, 3H), 7.58-7.44 (m, 3H), 7.38 (br s, 2H), 4.28-4.18 (m, 2H), 4.09-4.02 (m, 2H), 3.85-3.71 (m, 3H), 2.88 (s, 4H), 2.17-2.06 (m, 3H) 1.125 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 4.16 (s, 2H), 3.90 (s, 2H), 3.24 (q, J = 10.7 Hz, 2H), 2.90 (s, 4H), 2.10 (s, 3H), 2.09 (s, 3H) 1.126 1H NMR (400 MHz, methanol) = 8.50-8.45 (m, 1H), 7.88 (dd, 1H), 7.68-7.62 (m, 1H), 7.61 (s, 2H), 4.27- 4.18 (m, 2H), 3.90-3.81 (m, 2H), 2.89 (s, 4H), 2.13 (d, 6H), 1.67-1.56 (m, 1H), 0.94-0.78 (m, 4H) 1.127 1H NMR (400 MHz, methanol) = 8.85-8.78 (m, 1H), 8.17-8.10 (m, 1H), 8.04-8.00 (m, 1H), 7.76-7.69 (m, 1H), 6.83 (s, 1H), 6.75 (s, 1H), 3.92 (s, 4H), 3.64 (s, 3H), 2.67 (s, 4H), 2.00 (s, 3H), 1.94 (s, 3H) 1.128 1H NMR (400 MHz, methanol) = 8.93 (dd, J = 0.7, 2.1 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.7, 8.4 Hz, 1H), 7.78 (s, 2H), 4.17 (s, 2H), 4.02 (s, 2H), 3.92 (s, 2H), 3.39 (s, 3H), 2.92 (s, 4H), 2.13 (s, 6H) 1.129 1H NMR (400 MHz, methanol) = 8.46 (d, 1H), 7.87 (dd, 1H), 7.64 (td, 1H), 7.59 (s, 2H), 3.94 (s, 4H), 2.82 (s, 4H), 2.12 (s, 6H), 1.22 (s, 9H) 1.130 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.30-4.21 (m, 3H), 3.93- 3.78 (m, 4H), 3.74-3.66 (m, 2H), 3.65-3.57 (m, 2H), 2.87 (d, J = 5.5 Hz, 4H), 1.99 (s, 3H), 1.98 (s, 6H) 1.131 1H NMR (400 MHz, methanol) = 8.34 (d, J = 5.1 Hz, 1H), 7.53 (td, J = 1.5, 5.1 Hz, 1H), 7.32 (s, 1H), 7.04 (d, J = 3.8 Hz, 2H), 4.26 (s, 2H), 4.06 (s, 2H), 2.92 (s, 4H), 1.99 (d, J = 1.5 Hz, 6H) 1.95 (s, 3H) 1.132 0 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 5.15 (dqd, J = 1.8, 6.8, 48.4 Hz, 1H), 4.25 (br s, 2H), 3.91 (d, J = 3.1 Hz, 2H), 3.76 (d, J = 3.3 Hz, 3H), 2.88 (d, J = 2.8 Hz, 4H), 2.09 (s, 3H), 1.53 (ddd, J = 1.6, 6.7, 24.5 Hz, 3H) 1.133 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 4.12 (s, 2H), 3.89 (s, 2H), 2.91 (s, 4H), 2.71-2.65 (m, 2H), 2.60-2.54 (m, 2H), 2.09 (d, J = 3.3 Hz, 6H) 1.134 1.135 1H NMR (400 MHz, methanol) = 8.67-8.60 (m, 1H), 8.49 (d, 1H), 8.05- 8.00 (m, 1H), 7.98-7.88 (m, 2H), 7.70-7.62 (m, 1H), 7.54-7.47 (m, 1H), 7.40 (s, 2H), 4.58 (d, 2H), 4.08 (d, 2H), 3.80 (d, 3H), 2.88 (s, 4H), 2.15 (d, 3H) 1.136 1H NMR (400 MHz, methanol) = 8.35 (d, J = 5.3 Hz, 1H), 7.63-7.56 (m, 2H), 7.56-7.52 (m, 1H), 7.33 (s, 1H), 7.28-7.22 (m, 2H), 7.16-7.09 (m, 2H), 4.30-4.22 (m, 2H), 4.07 (br s, 2H), 2.97-2.84 (m, 4H), 2.11 (s, 3H), 2.07 (s, 3H) 1.137 1H NMR (400 MHz, methanol) = 8.68 (d, J = 5.1 Hz, 1H), 8.20 (d, J = 7.7 Hz, 1H), 8.03 (dt, J = 1.6, 7.7 Hz, 1H), 7.68-7.58 (m, 3H), 7.27 (s, 2H), 7.14 (t, J = 8.8 Hz, 2H), 4.26-3.94 (m, 4H), 2.95 (s, 4H), 2.10 (s, 6H) 1.138 1H NMR (400 MHz, methanol) = 8.46 (d, 1H), 7.87 (dd, 1H), 7.67- 7.61 (m, 1H), 7.60 (s, 2H), 4.12 (s, 2H), 3.89 (s, 2H), 2.82 (s, 4H), 2.13 (s, 6H). Deuteration of alpha-CN protons observed. 1.139 .sup.1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.56 (s, 2H), 3.95 (s, 4H), 3.79 (s, 3H), 2.87 (s, 4H), 2.13 (s, 3H), 1.23 (s, 9H) 1.140 1H NMR (400 MHz, methanol) Shift = 7.67-7.60 (m, 2H), 7.15 (tt, J = 2.0, 8.8 Hz, 2H), 7.06 (d, J = 0.9 Hz, 1H) 6.97 (d, J = 1.6 Hz, 1H), 3.78 (d, J = 4.5 Hz, 4H), 3.77 (s, 3H), 3.16 (q, J = 7.3 Hz, 2H), 2.83 (d, J = 1.2 Hz, 4H), 2.09 (s, 3H), 1.10 (t, J = 7.2 Hz, 3H) 1.141 1H NMR (400 MHz, methanol) Shift = 7.67-7.59 (m, 2H), 7.15 (tt, J = 2.8, 8.9 Hz, 2H), 7.05 (d, J = 0.7 Hz, 1H), 6.97 (d, J = 1.1 Hz, 1H), 3.76 (s, 7H), 2.82 (d, J = 2.6 Hz, 4H), 2.09 (s, 3H), 1.32 (s, 9H) 1.142 0 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.27 (s, 2H), 7.16- 7.10 (m, 2H), 4.34 (br s, 2H), 3.84 (br s, 2H), 2.88 (s, 4H), 2.09 (s, 6H), 1.22 (s, 9H) 1.143 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.17 (s, 2H), 4.05 (s, 2H), 3.88 (s, 2H), 3.53 (q, J = 7.0 Hz, 2H), 2.87 (s, 4H), 1.99 (s, 3H), 1.98 (s, 6H), 1.21 (t, J = 7.0 Hz, 3H) 1.144 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.45 (s, 2H), 3.92 (s, 2H), 2.90 (d, J = 1.5 Hz, 4H), 1.99 (s, 3H), 1.98 (s, 6H), 1.56 (s, 6H) 1.145 1.146 1H NMR (400 MHz, methanol) = 7.64-7.57 (m, 2H), 7.27 (s, 2H), 7.18- 7.10 (m, 2H), 4.33-4.23 (m, 3H), 3.93-3.87 (m, 3H), 3.85-3.79 (m, 1H), 3.75-3.67 (m, 2H), 3.66-3.57 (m, 2H), 2.89 (d, J = 5.4 Hz, 4H), 2.09 (s, 6H) 1.147 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (s, 1 H) 7.70 (s, 1 H) 6.72 (d, J = 6.36 Hz, 1 H) 4.42 (d, J = 4.77 Hz, 2 H) 4.00 (s, 2 H) 3.67- 3.78 (m, 5 H) 2.77 (br s, 4 H) 2.04 (s, 3 H) 1.148 .sup.1H NMR (400 MHz, methanol) = 7.49 (d, J = 1.0 Hz, 1 H) 6.85 (s, 1H), 6.77 (s, 1H), 4.28 (s, 2H), 3.98 (d, J = 7.5 Hz, 3H), 3.92 (d, J = 2.6 Hz, 2H), 3.67 (d, J = 1.1 Hz, 3H), 2.85 (s, 4H), 2.01 (s, 3H), 1.99 (s, 3H) 1.149 1H NMR (400 MHz, methanol) = 6.84 (s, 1H), 6.77 (s, 1H), 3.86-3.80 (m, 4H), 3.66 (s, 3H), 2.86 (s, 4H), 2.67-2.57 (m, 1H), 2.00 (s, 3H), 1.98 (s, 3H), 1.11-1.03 (m, 4H) 1.150 1H NMR (400 MHz, methanol) = 8.53-8.46 (m, 1H), 7.95-7.88 (m, 1H), 7.67 (dd, 1H), 7.39 (s, 2H), 3.85- 3.80 (m, 4H), 3.78 (s, 3H), 3.10 (q, 2H), 2.87 (s, 4H), 2.11 (s, 3H), 1.34 (t, 3H) 1.151 1H NMR (400 MHz, methanol) = 7.63-7.57 (m, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 3.78 (s, 4H), 2.85 (s, 4H), 2.09 (s, 6H), 1.32 (s, 9H) 1.152 0 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.56 (s, 2H), 3.82-3.75 (m, 7H), 3.16 (q, 2H), 2.91-2.78 (m, 4H), 2.13 (s, 3H), 1.11 (t, 3H) 1.153 1H NMR (400 MHz, methanol) = 7.61 (dd, J = 5.4, 8.7 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 4.48 (s, 2H), 3.95 (s, 2H), 2.99-2.88 (m, 4H), 2.09 (s, 6H), 1.57 (s, 6H) 1.154 1H NMR (400 MHz, methanol) = 8.49 (d, 1H), 7.96-7.88 (m, 1H), 7.71- 7.62 (m, 1H), 7.39 (s, 2H), 4.01- 3.89 (m, 4H), 3.78 (s, 3H), 2.87 (s, 4H), 2.12 (s, 3H), 1.23 (s, 9H) 1.155 1H NMR (400 MHz, methanol) = 8.47 (d, 1H), 7.87 (dd, 1H), 7.65 (td, 1H), 7.60 (s, 2H), 4.33 (s, 2H), 3.84 (s, 2H), 2.85 (s, 4H), 2.12 (s, 6H), 1.22 (s, 9H) 1.156 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.56 (s, 2H), 3.80 (s, 3H), 3.77 (d, 4H), 2.89-2.76 (m, 4H), 2.13 (s, 3H), 1.33 (s, 9H) 1.157 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (d, J = 0.73 Hz, 1 H) 7.70 (s, 1 H) 4.16 (br s, 2 H) 3.70 (s, 3 H) 3.60-3.68 (m, 1 H) 3.65 (br dd, J = 9.84, 4.22 Hz, 1 H) 2.67-2.87 (m, 4 H) 2.04 (s, 3 H) 1.12 (s, 9 H) 1.158 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.7 Hz, 2H), 7.26 (s, 2H), 7.13 (t, J = 8.9 Hz, 2H), 4.16 (s, 2H), 4.02 (s, 2H), 3.91 (s, 2H), 3.39 (s, 3H), 2.90 (br s, 4H), 2.09 (s, 6H) 1.159 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.11 (s, 2H), 3.84 (s, 2H), 3.64 (t, J = 6.0 Hz, 2H), 3.33 (s, 3H), 2.86 (s, 4H), 2.39 (t, J = 6.0 Hz, 2H), 1.99 (s, 3H), 1.99-1.97 (m, 6H) 1.160 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.27 (s, 2H), 7.16- 7.10 (m, 2H), 4.14 (s, 2H)*, 3.91 (s, 2H), 3.65-3.62 (m, 2H), 2.91 (s, 4H), 2.09 (s, 6H) 1.161 1H NMR (400 MHz, methanol) = 7.64 (dd, J = 5.4, 8.8 Hz, 2H), 7.50 (d, J = 0.7 Hz, 1H), 7.15 (t, J = 8.8 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.30 (d, J = 2.6 Hz, 2H), 3.99 (d, J = 7.7 Hz, 3H), 3.95 (d, J = 3.5 Hz, 2H), 3.77 (d, J = 1.1 Hz, 3H), 2.88 (s, 4H), 2.10 (s, 3H) 1.162 0 1H NMR (400 MHz, methanol) = 7.63-7.58 (m, 2H), 7.27 (s, 2H), 7.17- 7.09 (m, 2H), 4.19 (s, 2H), 4.06 (s, 2H), 3.91 (s, 2H), 3.54 (q, J = 7.0 Hz, 2H), 2.90 (s, 4H), 2.09 (s, 6H), 1.22 (t, J = 7.0 Hz, 3H) 1.163 .sup.1H NMR (400 MHz, methanol) ppm 8.75 (s, 2 H) 7.88 (s, 1 H) 7.81 (d, J = 0.86 Hz, 1 H) 3.82 (d, J = 2.93 Hz, 4 H) 3.78 (s, 3 H) 3.09 (d, J = 7.34 Hz, 2 H) 2.87 (s, 4 H) 2.11 (s, 3 H) 1.33 (t, J = 7.40 Hz, 3 H) 1.164 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.6, 2.1 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.6, 8.4 Hz, 1H), 7.78 (s, 2H), 3.79 (s, 4H), 2.86 (s, 4H), 2.13 (s, 6H), 1.33 (s, 9H) 1.165 1.166 1H NMR (400 MHz, methanol) = 8.92 (d, J = 1.6 Hz, 1H), 8.17 (dd, J = 2.2, 8.3 Hz, 1H), 8.04 (d, J = 8.7 Hz, 1H), 7.78 (s, 2H), 3.85 (s, 4H), 3.15 (q, J = 7.3 Hz, 2H), 2.91 (s, 4H), 2.12 (s, 6H), 1.34 (t, J = 7.7 Hz, 3H) 1.167 1H NMR (400 MHz, methanol) = 8.51-8.47 (m, 1H), 7.95-7.89 (m, 1H), 7.70-7.62 (m, 1H), 7.39 (s, 2H), 4.15-4.09 (m, 2H), 3.92-3.86 (m, 2H), 3.79 (s, 3H), 2.86 (s, 4H), 2.12 (s, 3H) 1.168 1H NMR (400 MHz, methanol) = 8.64-8.61 (m, 1H), 8.04-8.01 (m, 1H), 7.94 (dt, J = 1.8, 7.7 Hz, 1H), 7.61 (dd, J = 5.5, 8.7 Hz, 2H), 7.51 (ddd, J = 1.2, 4.8, 7.6 Hz, 1H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 4.61 (s, 2H), 4.09 (s, 2H), 2.97-2.90 (m, 4H), 2.12 (s, 3H), 2.11 (s, 3H) 1.169 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.19 (dd, 1H), 8.08 (d, 1H), 7.57 (s, 2H), 4.18-3.89 (m, 6H), 3.81 (d, 3H), 3.58-3.52 (m, 2H), 2.88 (s, 4H), 2.13 (s, 3H), 1.23 (q, 3H) 1.170 1H NMR (400 MHz, methanol) = 8.48 (d, 1H), 7.91-7.84 (m, 1H), 7.69- 7.62 (m, 1H), 7.60 (s, 2H), 3.78 (s, 4H), 2.85 (s, 4H), 2.12 (s, 6H), 1.32 (s, 9H) 1.171 1H NMR (400 MHz, methanol) = 8.09 (d, J = 9.3 Hz, 1H), 7.27 (d, J = 9.2 Hz, 1H), 7.05 (s, 2H), 4.62 (s, 2H), 4.16 (s, 3H), 4.09 (s, 2H), 2.94 (s, 4H), 2.01 (s, 6H), 2.00 (s, 3H) 1.172 00 1H NMR (400 MHz, d6-DMSO) = 9.09 (d, 1H), 8.66-8.61 (m, 1H), 8.38 (dd, 1H), 8.23 (d, 1H), 8.00- 7.93 (m, 2H), 7.64-7.59 (m, 1H), 7.59-7.50 (m, 2H), 4.43 (d, 2H), 3.90 (s, 2H), 3.73 (d, 3H), 2.79 (s, 4H), 2.06 (d, 3H) 1.173 01 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 8.97 (s, 2 H) 7.80 (s, 1 H) 7.70 (s, 1 H) 3.97 (br d, J = 2.93 Hz, 2 H) 3.93 (d, J = 5.14 Hz, 2 H) 3.70 (s, 5 H) 3.28 (d, J = 5.75 Hz, 3 H) 2.76 (br s, 4 H) 2.04 (s, 3 H) 1.174 02 1H NMR (400 MHz, methanol) Shift = 7.69-7.57 (m, 2H), 7.21-7.09 (m, 2H), 7.06 (s, 1H), 6.97 (s, 1H), 4.27- 4.20 (m, 2H), 3.94-3.79 (m, 4H), 3.76 (s, 3H), 3.74-3.57 (m, 4H), 2.85 (d, J = 5.3 Hz, 4H), 2.09 (d, J = 1.3 Hz, 3H) 1.175 03 1H NMR (400 MHz, methanol) = 7.60 (dd, J = 5.4, 8.8 Hz, 2H), 7.27 (s, 2H), 7.13 (t, J = 8.8 Hz, 2H), 6.18 (t, J = 52.8 Hz, 1H), 4.30 (s, 2H), 3.99 (s, 2H), 2.93 (s, 4H), 2.09 (s, 6H) 1.176 04 .sup.1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.8 Hz, 2H), 7.14 (t, J = 8.9 Hz, 2H), 7.06 (s, 1H), 6.97 (s, 1H), 4.50-4.41 (m, 2H), 3.92 (s, 2H), 3.76 (s, 3H), 2.89 (s, 4H), 2.10 (s, 3H), 1.57 (s, 6H) 1.177 05 1H NMR (400 MHz, methanol) Shift = 7.65-7.57 (m, 2H), 7.51 (s, 1H), 7.27 (s, 2H), 7.18-7.09 (m, 2H), 4.32 (s, 2H), 3.98 (s, 3H), 3.97 (s, 2H), 2.92 (s, 4H), 2.10 (s, 6H) 1.178 06 .sup.1H NMR (400 MHz, DMSO-d.sub.6) ppm 10.70 (br d, J = 2.57 Hz, 1 H) 10.08 (s, 1 H) 8.97 (s, 2 H) 8.71 (d, J = 4.52 Hz, 1 H) 8.04-8.16 (m, 2 H) 7.81 (s, 1 H) 7.67-7.76 (m, 2 H) 3.75-4.17 (m, 4 H) 3.71 (s, 3 H) 2.59-3.05 (m, 4 H) 2.04 (s, 3 H) 1.179 07 1H NMR (400 MHz, methanol) = 6.85 (s, 1H), 6.77 (s, 1H), 4.08 (s, 2H), 3.82 (d, J = 3.7 Hz, 2H), 3.67 (s, 3H), 3.64 (dt, J = 0.9, 6.0 Hz, 2H), 3.33 (d, J = 1.3 Hz, 3H), 2.83 (s, 4H), 2.39 (dt, J = 2.9, 6.0 Hz, 2H), 2.00 (s, 3H), 1.99 (d, J = 2.3 Hz, 3H) 1.180 08 1H NMR (400 MHz, methanol) = 7.04 (s, 2H), 4.14 (s, 2H), 3.99-3.92 (m, 2H), 3.83 (s, 2H), 3.50-3.42 (m, 2H), 2.87 (s, 4H), 2.65-2.54 (m, 1H), 1.99 (s, 6H), 1.98 (s, 3H), 1.80-1.68 (m, 2H), 1.66-1.58 (m, 2H) 1.181 09 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.7, 2.1 Hz, 1H), 8.17 (dd, J = 2.2, 8.4 Hz, 1H), 8.04 (dd, J = 0.6, 8.3 Hz, 1H), 7.78 (s, 2H), 6.38- 6.02 (t, 1H), 4.31 (s, 2H), 4.00 (s, 2H), 2.95 (s, 4H), 2.13 (s, 6H) 1.182 0 1H NMR (400 MHz, methanol) = 8.92 (dd, J = 0.9, 2.2 Hz, 1H), 8.17 (dd, J = 2.3, 8.4 Hz, 1H), 8.06-8.00 (m, 1H), 7.78 (s, 2H), 4.23 (s, 2H), 3.87 (s, 2H), 2.96-2.88 (m, 4H), 2.15 (s, 3H), 2.13 (br s, 3H), 1.65-1.57 (m, 1H), 0.95-0.78 (m, 4H) 1.183 1H NMR (400 MHz, methanol) = 8.52-8.47 (m, 1H), 7.95-7.88 (m, 1H), 7.72-7.62 (m, 1H), 7.40 (s, 2H), 6.35-6.01 (m, 1H), 4.31-4.26 (m, 2H), 4.00-3.94 (m, 2H), 3.81-3.77 (m, 3H), 2.88 (s, 4H), 2.12 (s, 3H) 1.184 1H NMR (400 MHz, methanol) = 8.64 (t, J = 5.0 Hz, 1H), 8.07-8.01 (m, 1H), 7.99-7.93 (m, 1H), 7.64 (dd, J = 5.4, 8.8 Hz, 2H), 7.55-7.50 (m, 1H), 7.15 (t, J = 8.8 Hz, 2H), 7.07 (s, 1H), 6.98 (s, 1H), 4.59 (d, J = 3.3 Hz, 2H), 4.08 (d, J = 3.2 Hz, 2H), 3.78 (d, J = 4.8 Hz, 3H), 2.91 (s, 4H), 2.11 (d, J = 5.6 Hz, 3H) 1.185 1H NMR (400 MHz, Methanol) = 8.94 (d, 1H), 8.18 (dd, 1H), 8.08 (d, 1H), 7.68 (d, 2H), 7.62-7.42 (m 5H), 4.24 (s, 2H), 4.06 (d, 2H), 3.79 (d, 3H), 2.91 (s, 4H), 2.13 (d, 3H) 1.186 1.187 1H NMR (400 MHz, methanol) = 7.63-7.57 (m, 2H), 7.26 (s, 2H), 7.17- 7.10 (m, 2H), 3.80 (s, 4H), 3.16 (q, J = 7.2 Hz, 2H), 2.87 (s, 4H), 2.09 (s, 6H), 1.10 (t, J = 7.2 Hz, 3H) 1.188 1H NMR (400 MHz, methanol) = 8.66-8.61 (m, 1H), 8.50-8.46 (m, 1H), 8.05-8.01 (m, 1H), 7.97-7.91 (m, 1H), 7.91-7.86 (m, 1H), 7.69- 7.63 (m, 1H), 7.62 (s, 2H), 7.54-7.48 (m, 1H), 4.61 (s, 2H), 4.09 (s, 2H), 2.94 (s, 4H), 2.14 (d, 6H) 1.189 .sup.1H NMR (400 MHz, methanol) ppm 8.76 (s, 2 H) 7.90 (s, 1 H) 7.83 (s, 1 H) 6.04-6.34 (m, 1 H) 4.28 (s, 2 H) 3.97 (s, 2 H) 3.79 (d, J = 2.57 Hz, 3 H) 2.89 (s, 4 H) 2.13 (s, 3 H) 1.190 1H NMR (400 MHz, methanol) = 7.63 (dd, J = 5.4, 8.9 Hz, 2H), 7.15 (t, J = 8.9 Hz, 2H), 7.06 (s, 1H), 6.98 (s, 1H), 4.17 (d, J = 3.5 Hz, 2H), 4.06 (d, J = 2.8 Hz, 2H), 3.89 (d, J = 3.9 Hz, 2H), 3.76 (d, J = 1.6 Hz, 3H), 3.55 (dq, J = 3.4, 7.0 Hz, 2H), 2.87 (s, 4H), 2.09 (s, 3H), 1.22 (q, J = 6.9 Hz, 3H) 1.191 1H NMR (400 MHz, DMSO-d.sub.6) = 10.90 (bs, 1H), 9.30 (s, 1H), 7.01 (s, 1H), 6.90 (s, 1H), 3.73-3.71 (m, 4H), 3.64 (s, 3H), 2.83 (m, 4H), 2.05 (s, 3H), 1.14-1.12 (m, 9H) 1.192 0 1H NMR (400 MHz, DMSO-d.sub.6) = 10.86 (br s, 1H), 7.01 (s, 1H), 6.91 (s, 1H), 5.68 (s, 1H), 3.65 (s, 3H), 3.55 (s, 4H), 2.74-2.56 (m, 4H), 2.05 (s, 3H), 1.22 (s, 9H) 1.193 1H NMR (400 MHz, methanol) = 7.00 (s, 1H), 6.87 (s, 1H), 6.16 (t, 1H), 4.25 (s, 2H), 3.94 (s, 2H), 3.70 (s, 3H), 2.86 (s, 4H), 2.02 (s, 3H) 1.194 1H NMR (400 MHz, DMSO-d.sub.6) = 10.93 (br s, 1H), 7.00 (s, 1H), 6.91 (s, 1H), 3.69-3.64 (m, 7H), 3.17-3.15 (m, 2H), 2.89 (m, 2H), 2.62 (m, 2H), 2.05 (s, 3H), 1.21 (m, 3H) 1.195 1H NMR (400 MHz, d6-DMSO, 100 C., VT) = 10.30 (bs, 1H), 6.99 (s, 1H), 6.90 (s, 1H), 3.85 (br, 4H), 3.68 (s, 3H), 2.74 (s, 4H), 2.05 (s, 3H), 1.78 (s, 3H) 1.196 1H NMR (400 MHz, methanol) = 7.00 (s, 1H), 6.87 (s, 1H), 4.16 (s, 2H), 3.81 (s, 2H), 3.70 (s, 3H), 2.89- 2.80 (m, 4H), 2.02 (s, 3H), 1.60-1.55 (m, 1H), 0.86-0.81 (m, 4H) 1.197 1H NMR (400 MHz, methanol) = 7.00 (s, 1H), 6.87 (s, 1H), 4.11 (br s, 2H), 4.00-3.99 (m, 2H), 3.86 (s, 2H), 3.70 (s, 3H), 3.38-3.36 (m, 3H), 2.83 (s, 4H), 2.02 (s, 3H) 1.198 1HNMR (400 MHz, d6-DMSO, VT, 100 C.) = 8.60 (m, 1H), 7.95-7.93 (m, 2H), 7.50 (m, 1H), 7.00 (s, 1H), 6.90 (s, 1H), 4.39 (m, 2H), 3.90 (m, 2H), 3.69 (s, 3H), 2.78 (s, 4H), 2.06- 2.04 (m, 3H) 1.199 1HNMR (400 MHz, d6-DMSO, VT, 100 C.) 9.38 (bs, 1H), 8.68-8.61 (m, 1H), 8.11-8.03 (m, 2H), 7.68-7.65 (m, 1H), 6.99 (s, 1H), 6.89 (s, 1H), 3.93-3.92 (m, 4H), 3.67 (s, 3H), 2.78 (s, 4H), 2.05 (s, 3H) 1.200 1HNMR (400 MHz, d6- DMSO, VT, 100 C.) 10.33 (bs, 1H), 6.99 (s, 1H), 6.90 (s, 1H), 4.06- 3.93 (m, 2H), 3.86-3.78 (m, 2H), 3.68 (s, 3H), 3.63 (s, 2H), 2.76 (bs, 4H), 2.06 (s, 3H). 1.201 1H NMR (400 MHz, methanol) = 7.66 (br s, 2H), 7.52-7.45 (m, 3H), 7.01-6.99 (m, 1H), 6.87 (br s, 1H), 4.20-4.19 (m, 2H), 4.02 (s, 2H), 3.71- 3.66 (m, 3H), 2.86 (s, 4H), 2.02 (s, 3H) 1.202 0 1H NMR (400 MHz, methanol) = 7.00 (s, 1H), 6.87 (s, 1H), 4.28 (br s, 2H), 3.80 (br s, 2H), 3.70 (s, 3H), 2.86-2.77 (m, 4H), 2.02 (s, 3H), 1.35- 1.19 (m, 9H) 1.203 1H NMR (400 MHz, methanol) = 7.64-7.61 (m, 2H), 7.14 (t, 2H), 7.05 (s, 1H), 6.96 (s, 1H), 4.07 (s, 2H), 3.83- 3.82 (m, 2H), 3.76 (s, 3H), 2.85- 2.81 (m, 4H), 2.09-2.08 (m, 3H), 1.90-1.89 (m, 3H) 1.204 1.205 1.206

(48) TABLE-US-00002 TABLE 2 Compound Structure NMR 2.001 1H NMR (400 MHz, CDCl.sub.3): = 7.08 (s, 2H), 4.01 (d, J = 8.44 Hz, 2H), 3.87-3.99 (m, 2H), 3.71 (s, 3H), 3.07 (s, 2H), 2.87 (d, J = 2.08 Hz, 2H), 2.03 (s, 3H), 1.98 (s, 6H), 1.90 (s, 3H).

(49) TABLE-US-00003 TABLE 3 Prior art comparator. Compound Structure C1 (Compound A-38 from WO2014/096289)

Biological Examples

(50) Seeds of a variety of test species are sown in standard soil in pots (Lolium perenne (LOLPE), Setaria faberi (SETFA), Echinochloa crus-galli (ECHCG), Avena fatua (AVEFA)). 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/h. 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=80-100%; 4=60-79%; 3=40-59%; 2=20-39%; 1=0-19%).

(51) TABLE-US-00004 TABLE B1 Application pre-emergence COMPOUND SETFA LOLPE AVEFA ECHCG 1.001 5 5 5 2 1.002 5 5 5 5 1.003 5 5 5 5 1.004 5 5 5 5 1.005 5 5 5 5 1.006 5 5 2 5 1.007 5 5 3 5 1.008 5 5 5 5 1.009 5 5 5 5 1.010 5 5 5 5 1.011 3 2 1 2 1.012 5 5 5 5 1.013 5 5 5 5 1.014 5 5 5 5 1.015 5 5 5 5 1.016 5 5 5 5 1.017 5 5 5 5 1.018 5 5 5 5 1.019 4 4 4 5 1.020 5 5 5 5 1.021 5 5 5 5 1.022 5 3 2 4 1.023 3 3 2 1 1.024 5 5 5 5 1.193 5 5 5 5 1.195 5 5 5 5 1.196 5 5 5 5 1.201 5 5 5 5 1.202 5 5 5 5 1.203 5 4 5 5 2.001 5 5 5 5

(52) TABLE-US-00005 TABLE B2 Application post-emergence COMPOUND ECHCG SETFA LOLPE AVEFA 1.001 5 5 5 5 1.002 5 5 5 5 1.003 5 5 5 5 1.004 5 5 5 5 1.005 5 5 5 5 1.006 5 5 5 5 1.007 5 4 5 4 1.008 5 5 5 5 1.009 5 5 5 5 1.010 5 5 5 5 1.011 3 5 3 3 1.012 5 5 5 4 1.013 5 5 5 5 1.014 5 5 5 5 1.015 5 5 5 5 1.016 5 5 5 5 1.017 4 5 5 5 1.018 5 5 5 5 1.019 4 5 5 5 1.020 5 5 5 5 1.021 5 5 5 5 1.022 5 5 5 5 1.023 5 5 5 5 1.024 5 5 5 5 1.193 5 5 5 5 1.195 5 5 5 5 1.196 5 5 5 5 1.201 5 5 5 5 1.202 5 5 5 5 1.203 5 5 5 5 2.001 5 5 5 5

(53) TABLE-US-00006 TABLE B3 Prior Art Comparison. Using procedures outlines above, wheat and barley crop plants and a representative weed species Panicum miliaceum (PANMI) are treated post-emergence with compound 1.001 of the present invention or comparator compound C1 (Compound A-38 from WO2014/096289) at the application rates indicated. The compounds were also applied to wheat in conjunction with the safener compound cloquintocet-mexyl (CQC) at 50 g/ha. Compound Rate Wheat Barley PANMI C1 60 70 90 100 125 80 90 100 60 + CQC 60 NT NT 1.001 60 0 0 100 125 0 0 100 60 + CQC 0 NT NT NT = not tested.

(54) These results demonstrate that the compounds of the present invention, exemplified using compound 1.001 exhibit significantly improved crop safety vis--vis structurally similar prior art compounds e.g C1 whilst retaining good overall weed control.