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HERBICIDAL MALONAMIDES

20230150989 · 2023-05-18

    Inventors

    Cpc classification

    International classification

    Abstract

    The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R.sup.1 to R.sup.9 represent groups such as hydrogen, halogen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

    ##STR00001##

    Claims

    1. A compound of formula (I) ##STR00731## wherein the substituents have the following meanings: R.sup.1 hydrogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.2 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.3 hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl; R.sup.4 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.4)-halocycloalkyl, (C.sub.1-C.sub.3)-alkoxy (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio; R.sup.5 hydrogen, halogen, nitro, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, hydroxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, hydroxy-(C.sub.3-C.sub.5)-cycloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxycarbonyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl; R.sup.6 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.7 (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.3-C.sub.6)-alkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano; R.sup.8 hydrogen, halogen, cyano, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.6)-cyanoalkyl, (C.sub.1-C.sub.3)-hydroxyalkyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.3)-cyanoalkoxy, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy, (C.sub.3-C.sub.5)-cycloalkyl-(C.sub.1-C.sub.3)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy, (C.sub.1-C.sub.3)-alkylthio; R.sup.9 hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy; X a bond (X.sup.0) or a divalent unit from the group consisting of (X.sup.1), (X.sup.2), (X.sup.3), (X.sup.4), (X.sup.5), and (X.sup.6): ##STR00732## R.sup.10-R.sup.15 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, NR.sup.bCO.sub.2R.sup.e, R.sup.a, or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.5)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-alkynyl, phenyl, imidazolyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C.sub.1-C.sub.2)-alkoxy; Y hydrogen, cyano, hydroxyl, Z, or (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.12)-alkenyl or (C.sub.2-C.sub.12)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR.sup.d, Z, OZ, NHZ, S(O).sub.nR.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CO.sub.2R.sup.e, CONR.sup.bR.sup.h, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)═NOR.sup.e; Z a three-, four-, five- or six-membered saturated, partly unsaturated, fully unsaturated or aromatic ring, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted by m radicals from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, S(O).sub.nR.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.e, NR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)═NOR.sup.e, R.sup.b, R.sup.c, R.sup.e and R.sup.f, and where the sulfur atoms and carbon atoms bear n oxo groups; R.sup.a (C.sub.1-C.sub.6)-alkyl, (C.sub.2-C.sub.4)-alkynyl or (C.sub.3-C.sub.6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxy, and (C.sub.1-C.sub.3)-alkoxy; R.sup.b hydrogen or R.sup.a; R.sup.c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O).sub.nR.sup.a or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy or (C.sub.3-C.sub.6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.d hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl-(C.sub.1-C.sub.3)-alkyl, phenyl-(C.sub.1-C.sub.3)-alkyl, furanyl-(C.sub.1-C.sub.3)-alkyl or (C.sub.2-C.sub.4)-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO.sub.2R.sup.a, CONR.sup.bR.sup.h, (C.sub.1-C.sub.2)-alkoxy, (C.sub.1-C.sub.3)-alkylthio, (C.sub.1-C.sub.3)-alkylsulfinyl, (C.sub.1-C.sub.3)-alkylsulfonyl, phenylthio, phenylsulfinyl, and henylsulfonyl; R.sup.e R.sup.d; R.sup.f (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkoxy; R.sup.h hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.1-C.sub.2)-alkoxy, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, or (C.sub.2-C.sub.4)-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO.sub.2R.sup.a, and (C.sub.1-C.sub.2)-alkoxy; m 0, 1, 2, 3, 4 or 5; n 0, 1 or 2; r 1, 2, 3, 4, 5 or 6; including their agriculturally acceptable salts, amides, esters or thioesters, provided the compounds of formula (I) have a carboxyl group.

    2. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.1 hydrogen; R.sup.9 hydrogen.

    3. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.2 hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl; R.sup.6 hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl.

    4. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.3 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl; R.sup.5 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl.

    5. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.4 hydrogen, halogen.

    6. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.7 (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.6)-alkenyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano.

    7. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.8 hydrogen, halogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-cycloalkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy.

    8. The compound as claimed in claim 1, wherein the substituents have the following meaning: X a bond.

    9. The compound as claimed in claim 1, wherein the substituents have the following meaning: X a bond; Y (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.8)-alkenyl or (C.sub.2-C.sub.8)-alkynyl, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, OR.sup.d, Z, OZ, NHZ, S(O).sub.nR.sup.a, SO.sub.2NR.sup.bR.sup.d, SO.sub.2NR.sup.bCOR.sup.e, CO.sub.2R.sup.e, CONR.sup.bR.sup.h, COR.sup.b, CONR.sup.eSO.sub.2R.sup.a, NR.sup.bR.sup.e, NR.sup.bCOR.sup.e, NR.sup.bCONR.sup.eR.sup.e, NR.sup.bCO.sub.2R.sup.e, NR.sup.bSO.sub.2R.sup.eNR.sup.bSO.sub.2NR.sup.bR.sup.e, OCONR.sup.bR.sup.e, OCSNR.sup.bR.sup.e, POR.sup.fR.sup.f and C(R.sup.b)═NOR.sup.e.

    10. The compound as claimed in claim 1, wherein the substituents have the following meaning: X a bond; Y Z; Z a four- or five-membered saturated or partly unsaturated ring, which is formed from r carbon atoms and n oxygen atoms, each substituted by m radicals from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eSO.sub.2R.sup.a, R.sup.b, R.sup.c, R.sup.e and R.sup.f.

    11. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.1 hydrogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-alkynyl, (C.sub.2-C.sub.3)-haloalkynyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.2 hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.3 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-haloalkynyl; R.sup.4 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.4)-halocycloalkyl, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-haloalkynyl; R.sup.5 hydrogen, halogen, hydroxyl, cyano, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.3-C.sub.5)-halocycloalkyl, (C.sub.1-C.sub.3)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-haloalkynyl; R.sup.6 hydrogen, halogen, (C.sub.1-C.sub.3)-alkyl, (C.sub.1-C.sub.3)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy, (C.sub.1-C.sub.3)-haloalkoxy; R.sup.7 methyl; R.sup.8 hydrogen or fluorine; R.sup.9 hydrogen, (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.1-C.sub.6)-haloalkyl, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)-haloalkenyl, (C.sub.2-C.sub.6)-alkynyl, (C.sub.2-C.sub.6)-haloalkynyl, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-haloalkoxy, (C.sub.1-C.sub.3)-alkoxy-(C.sub.1-C.sub.3)-alkoxy; X a bond; Y Z, or (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.8)-cycloalkyl, (C.sub.2-C.sub.8)-alkenyl or (C.sub.2-C.sub.8)-alkynyl, each substituted by m radicals from the group consisting of fluorine, CO.sub.2R.sup.e and CONR.sup.eSO.sub.2R.sup.a; Z four to five-membered saturated or partly unsaturated ring which is formed from r carbon atoms, n oxygen atoms, and which is substituted by m radicals from the group consisting of CO.sub.2R.sup.e, CONR.sup.bR.sup.h, CONR.sup.eSO.sub.2R.sup.a, R.sup.b, R.sup.c, R.sup.e and R.sup.f; R.sup.a (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy; R.sup.b hydrogen, or (C.sub.1-C.sub.6)-alkyl or (C.sub.3-C.sub.6)-cycloalkyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxy; R.sup.c fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O).sub.nR.sup.a or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy or (C.sub.3-C.sub.6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.e hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, phenyl-(C.sub.1-C.sub.3)-alkyl or (C.sub.2-C.sub.4)-alkynyl, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.f (C.sub.1-C.sub.3)-alkyl or (C.sub.1-C.sub.3)-alkoxy; R.sup.h hydrogen or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, or (C.sub.2-C.sub.4)-alkynyl each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C.sub.1-C.sub.2)-alkoxy; m 0, 1, 2, 3, 4 or 5; n 0, 1 or 2; r 1, 2, 3, 4, or 5.

    12. A composition comprising at least one compound as claimed in claim 1, and at least one auxiliary, which is customary for formulating crop protection compounds.

    13. The composition as claimed in claim 12, comprising a further herbicide.

    14. (canceled)

    15. A method for controlling unwanted vegetation comprising allowing a herbicidally effective amount of at least one compound as claimed in claim 1 to act on plants, their seed and/or their habitat.

    Description

    A CHEMISTRY EXAMPLES

    [0629] Chemical bonds, drawn as bars in chemical formulae (see e.g. Cpds I40, I60 below), indicate the relative stereochemistry on the ring system.

    Example 1

    Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter A)

    [0630] ##STR00488##

    [0631] Triethylamine (24.24 g, 240 mmol) was added dropwise to a solution of O1-benzyl O3-tert-butyl propanedioate (1) (30 g, 120 mmol) and tosyl azide (26 g, 132 mmol) in acetonitrile (300 mL) at 10° C. The mixture was stirred at 20° C. for 48 h. The mixture was concentrated and purified with silica gel chromatography (petroleum ether:ethyl acetate=5:1) to give O1-benzyl O3-tert-butyl-2-diazo propanedioate (2) (25 g, 75% yield) as yellow oil. 1H NMR: (400 MHz, CDCl3) δ 7.40-7.34 (m, 5H), 5.27 (s, 2H), 1.52 (s, 9H).

    ##STR00489##

    [0632] Dirhodiumtetraacetat ([Rh(OAc).sub.2].sub.2) (143 mg) was added to a solution of O1-benzyl O3-tert-butyl-2-diazo propanedioate (2) (20 g, 72.46 mmol), methanol (14 mL) in toluene (300 mL) at 15° C. The mixture was stirred for 16 h at 60° C. The mixture was filtered and the filtrate was concentrated, purified by silica gel chromatography eluted with (petroleum ether:tert-butyl methyl ether=5:1) to give O1-benzyl O3-tert-butyl 2-methoxypropanedioate (3) (19 g, 93% yield) as yellow oil. 1H NMR: (400 MHz, CDCl3) δ=7.43-7.30 (m, 5H), 5.32-5.20 (m, 2H), 4.33 (s, 1H), 3.55-3.46 (m, 3H), 1.39 (s, 9H).

    ##STR00490##

    [0633] To a solution of O1-benzyl O3-tert-butyl 2-methoxypropanedioate (3) (19 g, 67.85 mmol) in dichloromethane (150 mL) was added trifluoroacetic acid (TFA), (30 mL). The mixture was stirred for 6 h at 20° C. The mixture was added to water and extracted with dichloromethane, the organic layers were washed with water, brine, dried, concentrated to give compound 3-benzyloxy-2-methoxy-3-oxo-propanoic acid (4) (11.5 g, 75% yield) as yellow oil. 1H NMR: (400 MHz, CDCl3) δ=10.40 (br s, 1H), 7.43-7.30 (m, 5H), 5.28 (s, 2H), 4.51 (s, 1H), 3.53 (s, 3H).

    ##STR00491##

    [0634] 1-Propanephosphonic anhydride solution (T.sub.3P) (22.7 g, 35.71 mmol, 50% in ethyl acetate) was added to a solution of 3-benzyloxy-2-methoxy-3-oxo-propanoic acid (4) (4 g, 17.86 mmol) and 3,5-dichloro aniline (5) (3.45 g, 21.4 mmol) in acetonitrile (100 mL). The mixture was stirred at 70° C. for 16 h. The mixture was poured into ice water and extracted with ethyl acetate. The organic layers were washed with brine, dried, concentrated, purified by column chromatograph on silica gel eluted with (petroleum ether:tert-butyl methyl ether=5:1) to give benzyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoate 6 (5.5 g, 81% yield) as yellow oil. 1H NMR: (400 MHz, CDCl3) δ 8.33 (br s, 1H), 7.53 (d, J=1.8 Hz, 2H), 7.42-7.34 (m, 5H), 7.14 (t, J=1.8 Hz, 1H), 5.29 (s, 2H), 4.47 (s, 1H), 3.54 (s, 3H).

    ##STR00492##

    [0635] Palladium on Carbon (Pd/C) (1 g, 10%) was added to a solution of benzyl 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoate (6) (5.5 g, 14.98 mmol) in tetrahydrofuran (100 mL). The mixture was stirred for 2 h at 10° C. under hydrogen gas H.sub.2 (15 psi). The mixture was filtered over Celite pad; the filtrate was concentrated to give 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter A) (3.5 g, 84% yield) as a yellow solid. 1H NMR: (400 MHz, CD3OD) δ 7.69 (d, J=1.9 Hz, 2H), 7.18 (t, J=1.8 Hz, 1H), 4.48 (s, 1H), 3.53 (s, 3H).

    Example 2

    Synthesis of 3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoic acid (Inter B)

    [0636] Synthesis was carried out in analogy to Walker, Daniel P. et al Synthesis, (7), 1113-1119, 2011.

    ##STR00493##

    [0637] To a solution of methyl 4-bromofuran-2-carboxylate (1) CAS 58235-80-6 (6 g, 29.27 mmol) in toluene (60 mL) was added tert-butyl carbamate (BocNH.sub.2) (4.1 g, 35.12 mmol), potassium carbonate (10.1 g, 73.14 mmol), Cul (1.67 g, 8.78 mmol) and (CH.sub.3NHCH.sub.2).sub.2 (1.54 g, 17.56 mmol) at 15° C. Then, the mixture was stirred at 130° C. under N.sub.2 for 16 h. The mixture was diluted with water (150 mL), filtered and extracted with ethyl acetate (100 mL), the organic layers were washed with brine, dried, concentrated and purified by silica gel chromatography (petroleum ether:ethyl acetate=10:1) to give methyl 4-(tert-butoxycarbonylamino)furan-2-carboxylate (1.75 g) as white solid.

    ##STR00494##

    [0638] To a solution of dry Rhodium on Carbon (Rh/C) (2.5 g, cat.) in methanol (500 mL) was added methyl 4-(tert-butoxycarbonylamino)furan-2-carboxylate (2) (5 g, 20.66 mmol) at 15° C. Then the mixture was stirred at 30° C. under hydrogen gas (H.sub.2) (50 psi) for 16 h. The mixture was filtered and concentrated to give cis-4-(tert-butoxycarbonylamino)tetrahydrofuran-2-carboxylate (3) (3 g, 60% yield) as white solid which was used without further purification in the next step.

    ##STR00495##

    [0639] To a mixture cis-4-(tert-butoxycarbonylamino)tetrahydrofuran-2-carboxylate (3) (4.2 g, 17.15 mmol) in dichloromethane (140 mL) was added HCl in ethylacetate (140 ml, 1M) at 15° C. and stirred at 25° C. for 4 h. The mixture was concentrated to give methyl cis-4-aminotetrahydrofuran-2-carboxylate Inter B (3 g, crude) as white solid (HCl-salt). 1H NMR: (400 MHz, D2O) δ 4.62 (dd, J=8.9, 6.9 Hz, 1H), 4.15-4.00 (m, 3H), 3.79 (s, 3H), 2.88-2.78 (m, 1H), 2.19-2.11 (m,1H).

    Example 3

    Synthesis of methyl amide cis-N-(3,5-dichlorophenyl)-2-methoxy-N′-[-5-(methylcarbamoyl)-tetrahydrofuran-3-yl]propanediamide (Cpd. I.60)

    [0640] ##STR00496##

    [0641] To a mixture of Inter A (718 mg, 2.09 mmol) in acetotnitrile (15 mL) was added Inter B (467 mg, 2.59 mmol), 1-propanephosphonic anhydride solution (T.sub.3P) (2.47 g, 3.885 mmol) in ethyl acetate and diisopropylethylamine (1.85 mL, 17.36 mmol) at 25° C. and stirred at 75° C. for 2 h under N.sub.2. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over by sodium sulfate, concentrated and purified by prep-H PLC (acetonitrile/water with trifluoroacetic acid) to give the desired methyl cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]tetrahydrofuran-2-carboxylate (Cpd. I.40) (170 mg, 16.% yield) as a white solid. 1H NMR: (400 MHz, CDCl3) δ 8.86-8.95 (m, 1H) 7.49-7.60 (m, 3H) 7.13 (d, J=1.76 Hz, 1H), 4.52-4.73 (m, 2H), 4.26 (d, J=3.51 Hz, 1H), 3.94-4.08 (m, 2H) 3.80 (d, J=17.82 Hz, 3H), 3.67 (d, J=3.01 Hz, 3H), 2.50-2.61 (m, 1H), 2.09 (dt, J=7.09, 3.73 Hz, 1H).

    ##STR00497##

    [0642] To a mixture of methyl cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]tetrahydrofuran-2-carboxylate (2.7 g, 6.9 mmol) in tetrahydrofuran (32.4 mL) was added LiOH (1.16 g, 27.7 mmol) in water (10.8 mL) at 25° C. and stirred at 25° C. for 2 h. The mixture was poured into water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated and purified by prep-HPLC (trifluoroacetic acid 0.1%, acetonitrile-water) to give cis-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]tetrahydrofuran-2-carboxylate (Cpd. I.60) (1.3 g, 48.3% yield) as white solid. 1H NMR: (400 MHz, DMSO-d6) δ 10.34 (d, J=5.26 Hz, 1H), 8.30 (dd, J=16.22, 7.02 Hz, 1H), 7.78 (t, J=1.75 Hz, 2H), 7.32 (t, J=1.75 Hz, 1H), 4.27-4.41 (m, 3H) 3.90 (ddd, J=8.55, 6.36, 1.75 Hz, 1H), 3.64 (dt, J=8.66, 5.54 Hz, 1H), 3.37 (s, 3H), 1.93 (dtd, J=12.77, 6.22, 6.22, 2.85 Hz, 1H).

    Example 4

    Synthesis of Cpd. I.144

    [0643] ##STR00498##

    [0644] To a solution of dimethylmethoxy malonate (CAS 5018-30-4) (1) (7.6 g, 47 mmol) in dimethylformamide (50 mL) under argon was added sodium hydride (60%, 2.2 g) at 50° C. The resulting mixture was stirred at 50° C. for further 30 min until no more hydrogen gas evolved. After cooling down to room temperature, 1-Chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (selectfluor, CAS 140681-55-6) (25 g) was added. The resulting mixture was stirred over night at room temperature. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate (3×100 mL). The organic phase was dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to afford the crude product dimethyl 2-fluoro-2-methoxy-propanedioate (2) (7.9 g, 93% yield). 1H NMR: (400 MHz, CDCl3) δ 3.89 (s, 6H), 3.58 (s, 3H).

    ##STR00499##

    [0645] To dimethyl 2-fluoro-2-methoxy-propanedioate (2) (7.9 g, 44 mmol) in tetrahydrofuran/water (1:1) was added lithium hydroxide (LiOH) (1.05 g, 44 mmol). The reaction mixture was stirred at room temperature overnight. Tetrahydrofuran was removed under reduced pressure. The resulting aqueous solution was extracted with tert-butyl methyl ether (2×100 mL) and the organic phases discarded. The aqueous layer was adjusted to pH 1 using concentrated hydrochloric acid, extracted with ethyl acetate (3×100 mL). The organic phases were dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to afford the crude product 2-fluoro-2,3-dimethoxy-3-oxo-propanoic acid (3) (5.3 g, 73% yield). 1H NMR: (400 MHz, CDCl3) δ 3.92 (s, 3H), 3.61 (s, 3H).

    ##STR00500##

    [0646] Amide bond formation was carried out as described above (example 1, compound 6). Yield 56% for methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (4). 1H NMR: (400 MHz, CDCl3) δ 8.26 (s,1H), 7.57 (s, 2H), 7.18 (s, 1H), 3.92 (s, 3H), 3.63 (s, 3H).

    ##STR00501##

    [0647] To methyl 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (4) (3.8 g, 12 mmol) in 1,2-dichloroethane (100 mL) was added trimethyltin hydroxide (Me.sub.3SnOH) (4.4 g, 25 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h, then the reaction mixture was extracted with saturated sodium bicarbonate solution in water (3×100 mL). The combined organic phases were adjusted to pH 1 using concentrated hydrogen chloride solution in water. The resulting mixture was extracted with ethyl acetate (3×100 mL). The organic phases were dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to afford the crude 3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoate (5) (1.2 g, 33% yield). LC-MS (M+H).sup.+:295.8.

    ##STR00502##

    [0648] To a solution of the carboxylic acid (0.3 g) in dimethylformamide (DMF, 10 mL) the amine 6 (CAS 229613-83-6) was added. To the resulting solution was added HATU (0.42 g) and then diisopropylethylamine (0.53 mL). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and sat. aqueous bicarbonate solution (10 mL) The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-fluoro-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (0.2 g, 47%, 1.144) as a mixture of diastereoisomers (1:1). 1H NMR (500 MHz, Chloroform-d) δ 8.65 (s, 1H), 7.57 (d, J=1.8 Hz, 2H), 7.43-7.33 (m, 1H), 7.19-7.13 (m, 1H), 6.03-5.98 (m, 1H), 5.95-5.89 (m, 1H), 5.11-5.04 (m, 1H), 3.81-3.73 (m, 3H), 3.65-3.53 (m, 4H), 2.54-2.45 (m, 1H), 2.06-1.98 (m, 1H).

    Example 5

    Synthesis of methyl (1S,4R)-4-(methylamino)cyclopent-2-ene-1-carboxylate (Inter C)

    [0649] ##STR00503##

    [0650] To a solution of (1R,4S)-2-azabicyclo[2.2.1]hept-5-en-3-one (CAS 79200-56-9) (20.0 g, 183 mmol) in tetrahydrofuran (50 mL) sodium hydride (8.8 g, 0.22 mol) was added at 0° C. After stirring for 30 minutes iodomethane (52 g, 0.37 mmol) was added at 0° C. and the mixture stirred overnight. After quenching with sat. ammonium chloride solution (50 mL), the aqueous phase was separated and extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried over sodium sulfate and concentrated to give (1R,4S)-2-methyl-2-azabicyclo[2.2.1]hept-5-en-3-one (5.6 g, 25%) as a colorless oil.

    ##STR00504##

    [0651] To a solution of (1R,4S)-2-methyl-2-azabicyclo[2.2.1]hept-5-en-3-one (3.0 g, 24 mmol) in methanol (30 mL) thionyl chloride (3.5 mL, 49 mmol) were added at 0° C. After stirring for 3 h at room temperature, the mixture was concentrated to afford Inter C (2.6 g, 56%) as a colorless salt. 1H NMR (400 MHz, D.sub.2O) δ 6.29 (ddd, J=5.7, 2.5, 1.6 Hz, 1H), 6.03 (dt, J=5.7, 2.3 Hz, 1H), 4.37 (m, 1H), 3.81 (m, 1H), 3.75 (s, 3H), 2.70 (m, 4H), 2.16 (dt, J=14.7, 5.0 Hz, 1H).

    Example 6

    Synthesis of Cpd. I155

    [0652] ##STR00505##

    [0653] To a solution of the carboxylic acid (1.0 g, 3.6 mmol) in dimethylformamide (DMF,10 mL) the amine Inter C (0.79 g, 4.1 mmol) was added. To the resulting solution was added HATU (1.57 g, 4.13 mmol) and then diisopropylethylamine (1.8 mL, 11 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (30 mL) and sat. aqueous bicarbonate solution (30 mL) The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]-methyl-amino]cyclopent-2-ene-1-carboxylate (700 mg, 47%, 1.155) as a mixture of diastereoisomers (1:1). 1H NMR (400 MHz, Chloroform-d) δ 8.45 (m, 2H), 7.54 (m, 4H), 7.12 (m, 2H), 6.01 (m, 2H), 5.81 (m, 2H), 5.70 (m, 2H), 5.01 (m, 2H), 4.82 (d, J=7.6 Hz, 1H), 4.75 (d, J=5.7 Hz, 1H), 3.51 (m, 8H), 3.03 (d, J=4.8 Hz, 3H), 2.83 (d, J=3.4 Hz, 3H), 2.55 (m, 2H), 2.36 (m, 4H), 2.07 (m, 4H), 1.87 (m, 4H), 1.60 (m, 4H).

    Example 7

    Synthese of Cpd. I123

    [0654] ##STR00506##

    [0655] To a solution of the carboxylic acid (120 g) in dimethylformamide (DMF, 500 mL) the hydrochloride salt of methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate (88.1 g, 496 mmol) (CAS 229613-83-6) was added. To the resulting solution was added HATU (189 g, 496 mmol) and then diisopropylethylamine (220 mL). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (50 mL) and sat. aqueous bicarbonate solution (50 mL) The resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (105 g, 60%, I.123) as a mixture of diastereoisomers (1:1). 1H NMR (500 MHz, Chloroform-d) δ 9.14 (s, 1H), 9.08 (s, 1H), 7.53 (dd, J=5.8, 1.8 Hz, 4H), 7.27 (m, 2H), 7.09 (m, 2H), 5.92 (m, 4H), 5.06 (q, J=9.0 Hz, 2H), 4.27 (d, J=5.1 Hz, 2H), 3.73 (s, 6H), 3.66 (s, 3H), 3.64 (s, 3H), 3.54 (m, 2H), 2.49 (tt, J=13.8, 8.4 Hz, 2H), 1.95 (ddt, J=14.1, 10.6, 3.5 Hz, 2H).

    Example 8

    Synthese of Cpd. I.136

    [0656] ##STR00507##

    [0657] To methyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (Cpd. I.123) (6.0 g, 15 mmol) in 1,2-dichloroethane (100 mL) was added trimethyltin hydroxide (Me.sub.3SnOH) (5.4 g, 30 mmol) at room temperature. The reaction mixture was stirred at room temperature for 16 h, then the reaction mixture was extracted with saturated sodium bicarbonate solution in water (3×100 mL). The combined organic phases were adjusted to pH 1 using concentrated hydrogen chloride solution in water. The resulting mixture was extracted with ethyl acetate (3×100 mL). The organic phases were dried over sodium sulfate. The dried organic phase was filtered and concentrated under reduced pressure to afford the crude (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene carboxylic acid (5.0 g, 86% yield, 1.136) as a mixture of diastereoisomers (1:1). 1H NMR (500 MHz, Chloroform-d) δ 9.18 (s, 1H), 9.13 (s, 1H), 7.53 (m, 4H), 7.38 (m, 2H), 7.10 (m, 2H), 5.97 (m, 4H), 5.07 (s, 2H), 4.29 (m, 2H), 3.61 (m, 8H), 2.53 (m, 2H), 1.99 (m, 2H).

    Example 9

    Synthesis of Cpd. I.142

    [0658] ##STR00508##

    [0659] To a solution of the carboxylic acid (Cpd. I.136) (500 mg, 1.29 mmol) in dimethylformamide (DMF, 10 mL) 2-chloroethanol (0.26 mL, 3.9 mmol) was added. To the resulting solution was added HATU (540 mg, 1.42 mmol) and then triethylamine (0.68 mL, 3.9 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and sat. aqueous bicarbonate solution (10 mL) The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding 2-chloroethyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (260 mg, 45%, I.142) as a mixture of diastereoisomers (2:1). 1H NMR (500 MHz, Chloroform-d) δ 9.08 (m, 2H), 7.52 (m, 4H), 7.20 (s, 1H), 7.10 (m, 2H), 5.94 (m, 4H), 5.11 (m, 2H), 4.37 (m, 4H), 4.27 (m, 2H), 3.69 (m, 13H), 2.57 (m, 2H), 1.96 (m, 2H).

    Example 10

    Synthesis of Cpd. I.175

    [0660] ##STR00509##

    [0661] To a solution of carboxylic acid (Cpd. I.136) (200 mg, 0.517 mmol) in tetrahydrofuran (5 mL) dimethylformamide (DMF, 0.1 mL, 0.5 mmol) and oxalyl chloride (0.09 mL, 1.0 mmol) were added. After stirring for 1 h, sodium benzylate (CAS 20194-18-7) (60 mg, 0.45 mmol) was added to the mixture and stirring was continued for 3 h. After quenching the reaction with water (5 mL), the aqueous layer was separated and extracted with ethyl acetate (3×5 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding benzyl (1S,4R)-4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]cyclopent-2-ene-1-carboxylate (24 mg, 10%, I.175) as a mixture of diastereoisomers (1:1). LC-MS (M+H).sup.+:477.1.

    Example 11

    Synthesis of Cpd. I.201

    [0662] ##STR00510##

    [0663] To a solution of the carboxylic acid (Cpd. I.136) (300 mg, 0.775 mmol) in dimethylformamide (DMF, 5 mL) propargylamine (CAS 2450-71-7) (51 mg, 0.93 mmol) was added. To the resulting solution was added HATU (95%, 372 mg, 0.93 mmol) and then diisopropylethylamine (0.40 mL, 2.3 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (5 mL) and sat. aqueous bicarbonate solution (5 mL) The resulting mixture was extracted with ethyl acetate (3×10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding N-(3,5-dichlorophenyl)-2-methoxy-N′-[(1R,4S)-4-(prop-2-ynylcarbamoyl)cyclopent-2-en-1-yl]propanediamide (47 mg, 14%, I.201) as a mixture of diastereoisomers (1:1). 1H NMR (500 MHz, Chloroform-d) δ 8.98 (m, 2H), 7.66 (s, 2H), 7.55 (m, 4H), 7.10 (s, 2H), 5.92 (m, 6H), 5.05 (d, J=7.9 Hz, 2H), 4.25 (s, 2H), 4.08 (m, 4H), 3.66 (s, 3H), 3.64 (s, 3H), 3.33 (s, 2H), 2.42 (m, 2H), 2.27 (m, 2H), 1.93 (t, J=14.7 Hz, 2H).

    Example 12

    Synthesis of Cpd. I.26

    [0664] ##STR00511##

    [0665] To a solution of the carboxylic acid (Inter A) (10 g, 36 mmol) in dimethylformamide (DMF, 100 mL) methyl 4-aminobutyrate hydrochloride (CAS 13031-60-2) (5.5 g, 36 mmol) was added. To the resulting solution was added HATU (15 g, 40 mol) and then triethylamine (15 mL, 108 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (50 mL) and sat. aqueous bicarbonate solution (50 mL) The resulting mixture was extracted with ethyl acetate (3×100 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]butanoate (10.6 g, 78%, Cpd. I.26). 1H NMR (500 MHz, Chloroform-d) δ 9.29 (s, 1H), 7.51 (d, J=1.9 Hz, 2H), 7.08 (m, 2H), 4.31 (s, 1H), 3.68 (s, 3H), 3.64 (s, 3H), 3.37 (q, J=6.7 Hz, 2H), 2.38 (t, J=7.2 Hz, 2H), 1.89 (p, J=7.1 Hz, 2H).

    Example 13

    Synthesis of Cpd. I.116

    [0666] ##STR00512##

    [0667] To a solution of methyl 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]butanoate (Cpd. I.26) (700 mg, 1.86 mmol) in 1:1 mixture of water (20 mL) and THF (20 mL) lithium hydroxide (102 mg, 4.24 mmol) was added. After stirring overnight, the reaction was quenched with aqueous hydrochloride (1 nn, 10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure yielding 4-[[3-(3,5-dichloroanilino)-2-methoxy-3-oxo-propanoyl]amino]butanoic acid (550 mg, 82%) as a colorless oil. 1H NMR (500 MHz, Chloroform-d) δ 8.22 (s, 1H), 7.53 (d, J=1.8 Hz, 2H), 7.11 (s, 1H), 3.75 (d, J=5.9 Hz, 1H), 3.67 (s, 3H), 3.29 (td, J=7.0, 2.7 Hz, 2H), 3.22 (d, J=5.9 Hz, 1H), 2.37 (t, J=7.2 Hz, 2H), 1.90 (p, J=7.1 Hz, 2H).

    Example 14

    Synthesis of Cpd. I.202-A

    [0668] ##STR00513##

    [0669] To a solution of the carboxylic acid (Cpd. I.116) (200 mg, 0.551 mmol) in dichloromethane (30 mL) methanesulfonamide (157 mg, 1.65 mmol), 4-dimethylaminopyridine (DMAP, 20 mg, 0.17 mmol) and N,N′-dicyclohexylmethanediimine (DCC, 114 mg, 0.551 mmol) were added. After stirring overnight, the reaction was quenched with water (20 mL) and extracted with ethyl acetate (3×20 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding N-(3,5-dichlorophenyl)-N′-[4-(methanesulfonamido)-4-oxo-butyl]-2-methoxy-propanediamide (25 mg, 10%, Cpd. I.202-A). LC-MS (M+H).sup.+:439.9.

    Example 15

    Synthesis of Cpd. I.203

    [0670] ##STR00514##

    [0671] To a solution of the carboxylic acid Cpd. I.116 (200 mg, 0.551 mmol) in dimethylformamide (DMF, 10 mL) methoxy(methyl)ammoniumchloride (80.6 mg, 0.826 mmol) was added. To the resulting solution was added HATU (314 mg, 0.826 mol) and then triethylamine (0.23 mL, 1.62 mmol). The resulting reaction mixture was stirred at room temperature overnight. To the reaction mixture was added water (10 mL) and sat. aqueous bicarbonate solution (10 mL) The resulting mixture was extracted with ethyl acetate (3×10 mL). The combined organic phases were dried (sodium sulfate), filtered and evaporated under reduced pressure. The crude product was purified by column chromatography using ethyl acetate as solvent yielding N-(3,5-dichlorophenyI)-2-methoxy-N′-[4-[methoxy(methyl)amino]-4-oxo-butyl]propanediamide (180 mg, 81%, Cpd. I.203). 1H NMR (500 MHz, Chloroform-d) δ 9.12 (s, 1H), 7.53 (d, J=1.8 Hz, 2H), 7.21 (s, 1H), 7.10 (t, J=1.8 Hz, 1H), 4.26 (s, 1H), 3.66 (s, 3H), 3.65 (s, 3H), 3.37 (qd, J=6.6, 3.9 Hz, 2H), 3.17 (s, 3H), 2.50 (m, 2H), 1.90 (m, 2H).

    [0672] High Performance Liquid Chromatography: HPLC-column Kinetex XB C18 1.7μ (50×2.1 mm); eluent:acetonitrile/water+0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60° C., flow gradient from 0.8 to 1.0 ml/min in 1.5 min).

    [0673] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.1 and R.sup.9 are hydrogen, were prepared, starting from commercially available diesters and using commercially available amines:

    ##STR00515##

    TABLE-US-00002 TABLE 2A Cpd. R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 R.sup.8 N*—X—Y HPLC/MS I1 H Cl H Cl H CH.sub.3 H [00516]embedded image 362.8 I2 H Cl H Cl H CH.sub.3 H [00517]embedded image 348.8 I3 H Cl H Cl H CH.sub.3 H [00518]embedded image 390.8 I4 H Cl H Cl H CH.sub.3 H [00519]embedded image 363 I5 H Cl H Cl H CH.sub.3 CH.sub.3 [00520]embedded image 376.8 I6 H Cl H Cl H CH.sub.3 CH.sub.3 [00521]embedded image 404.8 I7 H F H F H CH.sub.3 CH.sub.3 [00522]embedded image 372.9 I9 H Cl H Cl H CH.sub.3 H [00523]embedded image 376.7 I12 H Cl H Cl H CH.sub.2CH.sub.3 H [00524]embedded image 404.9 I13 H F H F H CH.sub.3 H [00525]embedded image 344.8 I15 F F H F F CH.sub.3 H CH.sub.3 294.9 I16 H Cl H Cl H CH.sub.3 H C(CH.sub.3).sub.3 332.8 I17 H F H H H CH.sub.3 H [00526]embedded image 340.9 I18 F F H F F CH.sub.3 H [00527]embedded image 395 I19 H Cl H Cl H CH.sub.3 H [00528]embedded image 390.8 I20 H Cl H Cl H CH.sub.3 H [00529]embedded image 392.7 I21 H Cl H Cl H CH.sub.3 H [00530]embedded image 418.8 I22 H F H F H CH.sub.3 H [00531]embedded image 360.9 I23 H F H F H CH.sub.3 H [00532]embedded image 387 124 H F H H H CH.sub.3 H [00533]embedded image 327 I25 F F H F F CH.sub.3 H [00534]embedded image 381 I26 H Cl H Cl H CH.sub.3 H [00535]embedded image 376.9 I27 H Cl H Cl H CH.sub.3 H [00536]embedded image 388.9 I28 H F H F H CH.sub.3 H [00537]embedded image 330.8 I29 H Cl H Cl H CH.sub.3 H [00538]embedded image 316.7 I30 F F H F F CH.sub.3 H [00539]embedded image 320.8 I31 F F F F F CH.sub.3 H [00540]embedded image 398.8 I33 H F F F H CH.sub.3 H [00541]embedded image 362.9 I34 H Br H CH.sub.3 H CH.sub.3 H [00542]embedded image 402.7 I35 H CH.sub.3 H Br H CH.sub.3 H [00543]embedded image 388.7 I36 H Cl H Cl H CH.sub.3 H [00544]embedded image 402.9 I37 H Cl H Cl H CH.sub.3 H [00545]embedded image 517.9 I38 H F H F H CH.sub.3 H [00546]embedded image 344.8 I39 H F H F H CH.sub.3 H [00547]embedded image 356.9 I40 H Cl H Cl H CH.sub.3 H [00548]embedded image 404.9 I41 H Cl H Cl H CH.sub.3 H [00549]embedded image 406.9 I42 H Cl H Cl H CH.sub.3 H [00550]embedded image 430.9 I44 H Cl H Cl H CH.sub.3 H [00551]embedded image 375.8 I45 H CH.sub.3 H CH.sub.3 H CH.sub.3 H [00552]embedded image 337 I46 H Cl H Cl H CH.sub.3 H [00553]embedded image 402.9 I47 H F H F H CH.sub.3 H [00554]embedded image 374.8 I48 H Cl H Cl H CH.sub.3 H [00555]embedded image 461.9 I49 H Cl H Cl H CH.sub.3 H [00556]embedded image 448 I50 H Cl H Cl H CH.sub.2CF.sub.3 H [00557]embedded image 445.0 I51 H Cl H Cl H CH.sub.3 H [00558]embedded image 388.8 I52 H Cl H Cl H CH.sub.3 H [00559]embedded image 360.9 I53 H Cl H Cl H CH.sub.3 H CH.sub.3 290.8 I54 H Cl H Cl H CH.sub.3 H [00560]embedded image 392.8 I55 H Cl H Cl H CH.sub.3 H [00561]embedded image 404.8 I56 H F H F H CH.sub.3 H [00562]embedded image 360.8 I57 H F H F H CH.sub.3 H [00563]embedded image 372.9 I58 H Cl H Cl H CH.sub.3 H [00564]embedded image 404.8 I59 H F H F H CH.sub.3 H [00565]embedded image 373.0 I60 H Cl H Cl H CH.sub.3 H [00566]embedded image 390.9 I61 H Cl H CH.sub.3 H CH.sub.3 H [00567]embedded image 356.8 I62 H F H CH.sub.3 H CH.sub.3 H [00568]embedded image 340.8 I63 H Cl H Cl H CH.sub.3 H [00569]embedded image 403.9 I64 H Cl H Cl H CH.sub.3 H [00570]embedded image 390.8 I65 H Cl H Cl H CH.sub.3 H [00571]embedded image 434 I66 H Cl H Cl H CH.sub.3 H [00572]embedded image 402.8 I67 H Cl H Cl H CH.sub.3 H [00573]embedded image 432.8 I68 H Cl H Cl H CH.sub.3 H [00574]embedded image 390.8 I69 H Cl H Cl H CH.sub.3 H [00575]embedded image 416.9 I70 H Cl H Cl H CH.sub.3 H [00576]embedded image 390.8 I71 H Cl H Cl H CH.sub.3 H [00577]embedded image 360.8 I72 H Cl H Cl H CH.sub.3 H [00578]embedded image 412.7 I74 H Cl H Cl H CH.sub.3 H [00579]embedded image 388.8 I75 H Cl H Cl H CH.sub.3 H [00580]embedded image 402.8 I76 H Cl H Cl H CH.sub.3 H [00581]embedded image 428.8 I77 H Cl H Cl H CH.sub.3 H [00582]embedded image 362.8 I78 H Cl H Cl H CH.sub.3 H [00583]embedded image 434.8 I79 H Cl H Cl H CH.sub.3 H [00584]embedded image 378.7 I80 H Cl H Cl H CH.sub.3 H [00585]embedded image 422.8 I81 H Cl H Cl H CH.sub.3 H [00586]embedded image 416.8 I82 H Cl H Cl H CH.sub.3 H [00587]embedded image 392.8 I83 H Cl H Cl H CH.sub.3 H [00588]embedded image 402.8 I84 H Cl H Cl H CH.sub.3 H [00589]embedded image 376.7 I85 H Cl H Cl H CH.sub.3 H [00590]embedded image 374.7 I86 H Cl H Cl H CH.sub.3 H [00591]embedded image 516.8 I89 H Cl H Cl H CH.sub.3 H [00592]embedded image 559.9 I91 H Cl H Cl H CH.sub.3 H [00593]embedded image 524.9 I92 H Cl H Cl H CH.sub.3 H [00594]embedded image 536.8 I93 H Cl H Cl H CH.sub.3 H [00595]embedded image 430.8 I94 H Cl H Cl H CH.sub.3 H [00596]embedded image 416.9 I95 H Cl H Cl H CH.sub.3 H [00597]embedded image 444.8 I96 H Cl H Cl H CH.sub.3 H [00598]embedded image 402.9 I97 H Cl H Cl H CH.sub.3 H [00599]embedded image 418.9 I98 H Cl H Cl H CH.sub.3 H [00600]embedded image 420.8 I99 H Cl H Cl H CH.sub.3 H [00601]embedded image 424.8 I100 H F H F H CH.sub.3 H [00602]embedded image 372.0 I101 H F H F H CH.sub.3 H [00603]embedded image 359.0 I102 H Cl H Cl H CH.sub.3 H [00604]embedded image 426.8 I103 H Cl H Cl H CH.sub.3 H [00605]embedded image 420.9 I104 H F H F H CH.sub.3 H [00606]embedded image 357 I105 H Cl H Cl H CH.sub.3 H [00607]embedded image 405 I106 H Cl H Cl H CH.sub.3 H [00608]embedded image 434 I107 H Cl H Cl H CH.sub.3 H [00609]embedded image 388.8 I108 H Cl H Cl H CH.sub.3 H [00610]embedded image 402.9 I109 H F H F H CH.sub.3 H [00611]embedded image 370.8 I110 H Cl H Cl H CH.sub.3 H [00612]embedded image 401 I111 H Cl H Cl H CH.sub.3 H [00613]embedded image 404.8 I112 H Cl H Cl H CH.sub.3 H [00614]embedded image 404.8 I113 H Cl H Cl H CH.sub.3 H [00615]embedded image 401 I114 H Cl H Cl H CH.sub.3 H [00616]embedded image 432.8 I115 H Cl H Cl H CH.sub.3 H [00617]embedded image 404.9 I116 H Cl H Cl H CH.sub.3 H [00618]embedded image 362.7 I117 H Cl H Cl H CH.sub.3 H [00619]embedded image 427 I118 H Cl H Cl H CH.sub.3 H [00620]embedded image 445 I119 H Cl H Cl H CH.sub.3 H [00621]embedded image 391 I120 H Cl H Cl H CH.sub.3 H [00622]embedded image 421 I121 H Cl H Cl H CH.sub.3 H [00623]embedded image 426.9 I122 H F H F H CH.sub.3 H [00624]embedded image 359 I123 H Cl H Cl H CH.sub.3 H [00625]embedded image 400.7 I124 H F H F H CH.sub.3 H [00626]embedded image 368.7 I125 H Cl H Cl H CH.sub.3 H [00627]embedded image 390.7 I126 H F H F H CH.sub.3 H [00628]embedded image 370.8 I127 OCH.sub.3 H H Cl H CH.sub.3 H [00629]embedded image 372.7 I128 H Cl H Cl H CH.sub.3 H [00630]embedded image 400.9 I129 H Cl H Cl H CH.sub.3 H [00631]embedded image 330.9 I130 H CN H H H CH.sub.3 H [00632]embedded image 334 I131 H Cl H Cl H CH.sub.3 H [00633]embedded image 388.9 I132 H Cl H Cl H CH.sub.3 H [00634]embedded image 388.9 I133 H Cl H Cl H CH.sub.3 H [00635]embedded image 389.0 I134 H Cl H Cl H CH.sub.3 H [00636]embedded image 406.5 I135 H CN H H H CH.sub.3 H [00637]embedded image 358 I136 H Cl H Cl H CH.sub.3 H [00638]embedded image 386.7 I137 H F H F H CH.sub.3 H [00639]embedded image 354.8 I138 H Cl H Cl H CH.sub.3 H [00640]embedded image 451 I139 H Cl H Cl H CH.sub.3 H [00641]embedded image 445 I140 H F H F H CH.sub.3 H [00642]embedded image 419 I141 H F H F H CH.sub.3 H [00643]embedded image 413 I142 H Cl H Cl H CH.sub.3 H [00644]embedded image 450.9 I143 H F H F H CH.sub.3 H [00645]embedded image 417 I144 H Cl H Cl H CH.sub.3 F [00646]embedded image 418.7 HPLC/MS = MassChargeRatio

    [0674] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.2, R.sup.6, R.sup.8 and R.sup.9 are hydrogen, were prepared, starting from commercially available diesters and using commercially available amines:

    ##STR00647##

    TABLE-US-00003 TABLE 2B [00648]embedded image HPLC/MS = MassChargeRatio; Cpd. R.sup.1 R.sup.3 R.sup.4 R.sup.5 R.sup.7 N*—X—Y HPLC/MS I145 CH.sub.3 Cl H Cl CH.sub.3 [00649]embedded image 372.9 I146 [00650]embedded image Cl H Cl CH.sub.3 [00651]embedded image 441 I147 [00652]embedded image Cl H Cl CH.sub.3 [00653]embedded image 417 I148 [00654]embedded image F H F CH.sub.3 [00655]embedded image 409 I149 [00656]embedded image F H F CH.sub.3 [00657]embedded image 399 I150 CH.sub.3 Cl H H CH.sub.3 [00658]embedded image 338.7 I151 CH.sub.3 H Cl H CH.sub.3 [00659]embedded image 339.0 I152 CH.sub.3 Cl Cl H CH.sub.3 [00660]embedded image 372.9 I153 CH.sub.2CHF.sub.2 H H H CH.sub.3 [00661]embedded image 355

    [0675] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.6 and R.sup.8 are hydrogen, were prepared, starting from commercially available diesters and using commercially available amines:

    ##STR00662##

    TABLE-US-00004 TABLE 2C Cpd. R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.7 R.sup.9 N*—X—Y HPLC/MS I154 CH.sub.3 F H F H CH.sub.3 H [00663]embedded image 340.9 I155 H H Cl H Cl CH.sub.3 CH.sub.3 [00664]embedded image 414.9 I156 H H Cl H Cl CH.sub.3 CH.sub.3 [00665]embedded image 400.9 I157 H H Cl H Cl CH.sub.3 CH.sub.3 [00666]embedded image 455 HPLC/MS = MassChargeRatio

    [0676] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.1, R.sup.6 and R.sup.9 are hydrogen, were prepared, starting from commercially available diesters and using commercially available amines:

    ##STR00667##

    TABLE-US-00005 TABLE 2D [00668]embedded image HPLC/MS = MassChargeRatio Cpd. R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.7 R.sup.8 N*—X—Y HPLC/MS I158 H CH.sub.3 H CH.sub.3 CH.sub.3 H [00669]embedded image 360.8 I159 H Cl H Cl CH.sub.3 H [00670]embedded image 429 I160 H CN H CN CH.sub.3 H [00671]embedded image 380.9 I161 H F H CN CH.sub.3 H [00672]embedded image 403.9 I162 H F H H CH.sub.3 H [00673]embedded image 379 I163 H Cl H H CH.sub.3 H [00674]embedded image 395 I164 H F H OCH.sub.3 CH.sub.3 H [00675]embedded image 409 I165 H F H Cl CH.sub.3 H [00676]embedded image 413 I166 H F H CH.sub.3 CH.sub.3 H [00677]embedded image 393 I167 H Cl H CN CH.sub.3 H [00678]embedded image 420 I168 H Cl H Cl [00679]embedded image H [00680]embedded image 427 I169 H CH.sub.3 H Cl CH.sub.3 H [00681]embedded image 462.8 I170 H CH.sub.3 Cl H CH.sub.3 H [00682]embedded image 462.8 I171 H Cl CH.sub.3 Cl CH.sub.3 H [00683]embedded image 442.7 I172 H Cl H Cl CH.sub.2CCH H [00684]embedded image 425 I173 H Cl H Cl CHF.sub.2 H [00685]embedded image 437 I174 H Cl H Cl CH.sub.3 H [00686]embedded image 425.6 I175 H Cl H Cl CH.sub.3 H [00687]embedded image 478.5 I176 H Cl H Cl CH.sub.3 H [00688]embedded image 454.8 I177 H Cl H Cl CH.sub.3 H [00689]embedded image 468.8 I178 H Cl H Cl CF.sub.3 H [00690]embedded image 454.7 I179 H Cl H Cl CH.sub.3 H [00691]embedded image 466.8 I180 H Cl H Cl CH.sub.3 H [00692]embedded image 441 I181 H Cl H Cl CH.sub.3 H [00693]embedded image 473 I183 H Cl H Cl CH.sub.3 H [00694]embedded image 425 I184 H Cl H Cl CH.sub.3 H [00695]embedded image 440.9 I185 H Cl H Cl CH.sub.3 H [00696]embedded image 426.9 I186 H Cl Cl Cl CH.sub.3 H [00697]embedded image 436.8 I187 H OCH.sub.3 OCH.sub.3 OCH.sub.3 CH.sub.3 H [00698]embedded image 423.2 I188 H CH.sub.2CH.sub.3 H H CH.sub.3 H [00699]embedded image 361 I189 H I H H CH.sub.3 H [00700]embedded image 459.1 I190 H CN F H CH.sub.3 H [00701]embedded image 375.9 I191 H Cl CH.sub.3 H CH.sub.3 H [00702]embedded image 381.2 I192 H OCF.sub.2CHF.sub.2 H H CH.sub.3 H [00703]embedded image 449.1 I193 H H OCF.sub.3 H CH.sub.3 H [00704]embedded image 417 I194 H Cl SCF.sub.3 H CH.sub.3 H [00705]embedded image 466.9 I195 H CH.sub.3 F H CH.sub.3 H [00706]embedded image 365.2 I196 H Cl OCH.sub.2CH.sub.3 H CH.sub.3 H [00707]embedded image 411.2 I197 H OCH.sub.3 CH.sub.3 OCH.sub.3 CH.sub.3 H [00708]embedded image 407.2 I198 H OCF.sub.3 H H CH.sub.3 H [00709]embedded image 416.9 I200 H Cl H Cl CH.sub.3 H [00710]embedded image 424.9 I201 H Cl H Cl CH.sub.3 H [00711]embedded image 423.9 I202-A H Cl H Cl CH.sub.3 H [00712]embedded image 468.0 I202-B H Cl H Cl CH.sub.3 H [00713]embedded image 439.9 I203 H Cl H Cl CH.sub.3 H [00714]embedded image 406.2 I204 OCH.sub.3 H H Cl CH.sub.3 H [00715]embedded image 372.7 I205 H CN H H CH.sub.3 H [00716]embedded image 334 I206 H Cl H Cl [00717]embedded image H [00718]embedded image 403.1 I207 H Cl H Cl CF.sub.3 H [00719]embedded image 431 I208 H Cl H Cl CHF.sub.2 H [00720]embedded image 413 I209 H Cl H Cl CH.sub.2CF.sub.3 H [00721]embedded image 447.1 I210 H Cl Cl Cl CH.sub.3 H [00722]embedded image 410.7 I211 H Cl H Cl CH.sub.3 F [00723]embedded image 394.7 I212 H Cl H Cl CH.sub.3 F [00724]embedded image 362.9 I213 H Cl H Cl CH.sub.3 H [00725]embedded image 415.2 I214 H F H F CH.sub.3 H [00726]embedded image 382.1 I215 H F H F CH.sub.3 H [00727]embedded image 427.3 I216 H F H F CH.sub.3 H [00728]embedded image 437.3 I217 H F H F CH.sub.3 H [00729]embedded image 489.3 I218 H F H F CH.sub.3 H [00730]embedded image 499.4

    B USE EXAMPLES

    [0677] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

    [0678] The culture containers used were plastic flowerpots containing loamy sand with approximately 3.0% of humus as the substrate. The seeds of the test plants were sown separately for each species.

    [0679] For the pre-emergence treatment, the active ingredients, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the test plants had rooted. This cover caused uniform germination of the test plants, unless this had been impaired by the active ingredients. For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and only then treated with the active ingredients which had been suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.

    [0680] Depending on the species, the test plants were kept at 10-25° C. or 20-35° C., respectively. The test period extended over 2 to 4 weeks. During this time, the test plants were tended, and their response to the individual treatments was evaluated.

    [0681] Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the test plants, or complete destruction of at least the aerial moieties, and 0 means no damage, or normal course of growth. A good herbicidal activity is given at values of 70 to 90 and a very good herbicidal activity is given at values of 90 to 100.

    [0682] The test plants used in the greenhouse experiments were of the following species:

    TABLE-US-00006 Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Avena fatua ECHCG Echinocloa crus-galli LOLMU Lolium multiflorum POLCO Polygonum convolvulus SETFA Setaria faberi SETVI Setaria viridis

    [0683] At an application rate of 0.125 kg/ha, applied by the pre-emergence method: [0684] compounds I.159, I.185, I.191 showed very good herbicidal activity against AMARE. [0685] compound I.159 showed very good herbicidal activity against ALOMY. [0686] compound I.159 showed very good herbicidal activity against SETFA. [0687] compounds I.169, I.185 showed very good herbicidal activity against APESV. [0688] compounds I.169, I.191 showed good herbicidal activity against ECHCG. [0689] compound I.185 showed very good herbicidal activity against ABUTH.

    [0690] At an application rate of 0.250 kg/ha, applied by the pre-emergence method: [0691] compounds I.161, I.162, I.164, I.167, I.168, I.172, I.186, I.192, I.195, I.210 showed very good herbicidal activity against APESV. [0692] compounds I.155, I.156, I.157, I.173 showed good herbicidal activity against APESV. [0693] compounds I.163, I.192, I.198, I..210 showed very good herbicidal activity against ABUTH. [0694] compounds I.157, I.162, I.165, I.166, I.174, I.176, I.179, I.180, I.181, I.184, I.186 showed good herbicidal activity against ABUTH. [0695] compounds I.161, I.162, I.163, I.165, I.166, I.167, I.172, I.174, I.175, I.176, I.179, I.180, I.181, I.183, I.184, I.186, I.189, 198, I.210 showed very good herbicidal activity against AMARE. [0696] compounds I.164, I.188, I.190 showed good herbicidal activity against AMARE. [0697] compounds I.161, I.163, I.164, I.166, I.175, I.176, I.177, I.184, I.195, I.211 showed very good herbicidal activity against SETFA. [0698] compound I.173 showed good herbicidal activity against SETFA. [0699] compounds I.165, I.167, I.175, I.177, I.181, I.183, I.188, I.189, I.190, I.195, I.198 showed very good herbicidal activity against ECHCG. [0700] compound I.168 showed good herbicidal activity against ECHCG. [0701] compounds I.174, I.177, I.178, I.180, I.183, I.188, I.189, I.211 showed very good herbicidal activity against ALOMY.

    [0702] At an application rate of 0.500 kg/ha, applied by the pre-emergence method: [0703] compounds I.13, I.36 showed very good herbicidal activity against ALOMY. [0704] compounds I.13, I.64 showed very good herbicidal activity against AMARE. [0705] compounds I.9, I.28, I.33, I.39, I.51, I.55, I.57, I.58, I.62, I.104, I.108, I.109, I.113, I.122, I.123, I.124, I.158, I.205, I.207 showed very good herbicidal activity against APESV. [0706] compounds I.38, I.45, I.52, I.61, I.64, I.77, I.110, I.115, I.118, I.119, I.121, I.145, I.208 showed good herbicidal activity against APESV. [0707] compounds I.9, I.28, I.33, I.36, I.39, I.51, I.55, I.123, I.124, I.145 showed very good herbicidal activity against ECHCG. [0708] compounds I.34, I.45, I.108, I.205, I.207 showed good herbicidal activity against ECHCG. [0709] compounds I.57, I.104, I.158, I.208 showed very good herbicidal activity against SETFA. [0710] compounds I.58, I.109, I.145 showed good herbicidal activity against SETFA.

    [0711] At an application rate of 1,000 kg/ha, applied by the pre-emergence method: [0712] compound I.100 showed very good herbicidal activity against AMARE. [0713] compounds I.40, I.59, I.60, I.84, I.100, I.101 showed very good herbicidal activity against APESV. [0714] compounds I.63, I.68, I.95 showed good herbicidal activity against APESV. [0715] compound I.40 showed very good herbicidal activity against ECHCG. [0716] compound I.60 showed good herbicidal activity against ECHCG. [0717] compounds I.59, I.101 showed very good herbicidal activity against SETFA.

    [0718] At an application rate of 0.125 kg/ha, applied by the post-emergence method: [0719] compounds I.159, I.169, I.185, I.191, I.192 showed very good herbicidal activity against ALOMY. [0720] compounds I.17, I.170, I.171 showed good herbicidal activity against ALOMY. [0721] compounds I.159, I.185 showed very good herbicidal activity against AMARE. [0722] compound I.192 showed good herbicidal activity against AMARE. [0723] compounds I.159, I.185 showed very good herbicidal activity against ABUTH. [0724] compounds I.169, I.170, I.171, I.191, I.192 showed good herbicidal activity against ABUTH. [0725] compounds I.17, I.170, I.191 showed good herbicidal activity against AVEFA.

    [0726] At an application rate of 0.250 kg/ha, applied by the post-emergence method: [0727] compounds I.160, I.161, I.162, I.164, I.165, I.166, I.168, I.172, I.173, I.174, I.175, I.177, I.181, I.186, I.188, I.189, I.190, I.192, I.198, I.210, I.211 showed very good herbicidal activity against ALOMY. [0728] compounds I.155, I.156, I.197 showed good herbicidal activity against ALOMY. [0729] compounds I.160, I.161, I.162, I.163, I.164, I.165, I.166, I.167, I.168, I.172, I.173, I.174, I.175, I.176, I.177, I.180, I.181, I.183, I.184, I.186, I.189, I.195, I.198 showed very good herbicidal activity against ABUTH. [0730] compounds I.157, I.179, I.188, I.190, I.192, I.197, I.210 showed good herbicidal activity against ABUTH. [0731] compounds I.161, I.162, I.163, I.165, I.174, I.175, I.179, I.181, I.183, I.184, I.185, I.189, I.190, I.198 showed very good herbicidal activity against AMARE. [0732] compounds I.155, I.156, I.157, I.160, I.164, I.167, I.168, I.176, I.177, I.178, I.180, I.188, I.192 showed good herbicidal activity against AMARE. [0733] compounds I.163, I.172, I.173, I.178, I.211 showed very good herbicidal activity against AVEFA. [0734] compounds I.166, I.167, I.176, I.179, I.180, I.184, I.198 showed very good herbicidal activity against ECHCG. [0735] compound I.195 showed good herbicidal activity against ECHCG. [0736] compounds I.183, I.195, I.210, I.211 showed very good herbicidal activity against SETVI. [0737] compounds I.197 showed good herbicidal activity against SETVI.

    [0738] At an application rate of 0.500 kg/ha, applied by the post-emergence method: [0739] compounds I.47, I.51, I.104, I.108, I.109, I.158, I.205 showed very good herbicidal activity against ABUTH. [0740] compounds I.52, I.55, I.145, I.204 showed good herbicidal activity against ABUTH. [0741] compounds I.2, I.3, I.4, I.13, I.33, I.34, I.35, I.36, I.38, I.39, I.46, I.64, I.104, I.113, I.205 showed very good herbicidal activity against ALOMY. [0742] compounds I.5, I.6, I.18, I.23, I.26, I.27, I.41, I.45, I.54, I.70, I.74, I.80, I.83, I.105, I.110, I.208 showed good herbicidal activity against ALOMY [0743] compounds I.5, I.13, I.57, I.58, I.108, I.109, I.122, I.123, I.124 showed very good herbicidal activity against AMARE. [0744] compounds I.26, I.47, I.41, I.54, I.56, I.80, I.117, I.118, I.119, I.120, I.121, I.145, I.158, I.204, I.205 showed good herbicidal activity against AMARE. [0745] compound I.42 showed good herbicidal activity against APESV. [0746] compounds I.2, I.3, I.4, I.9, I.33, I.38, I.39, I.64, I.110, I.145, I.208 showed very good herbicidal activity against AVEFA