CONDENSED ISOXAZOLINE DERIVATIVES AND THEIR USE AS HERBICIDES

Abstract

The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R.sup.1 to R.sup.6 represent groups such as hydrogen, halo-gen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; W is a bicyclic heterocycle; 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) ##STR00191## 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, (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)-haloalkoxy, (C.sub.2-C.sub.3)-haloalkenyl, (C.sub.2-C.sub.3)-haloalkynyl; 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, (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; W a divalent unit selected from the group consisting of (W.sup.1) to (W.sup.24), and wherein the divalent unit is substituted by m radicals from the group consisting of R.sup.k and R.sup.l, and where carbon atoms bear n oxo groups: ##STR00192## ##STR00193## ##STR00194## 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): ##STR00195## R.sup.7-R.sup.12 each independently hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO.sub.2R.sup.e, CONR.sup.bR.sup.d, 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, 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 or (C.sub.3-C.sub.6)-alkynyloxy, 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 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, (C.sub.1-C.sub.3)-alkoxy 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 phenylsulfonyl; 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; R.sup.k (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (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, hydroxyl and (C.sub.1-C.sub.2)-alkoxy; R.sup.l fluorine, chlorine, bromine, iodine, cyano, hydroxyl or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl; 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; with the exception of 3-phenyl-3a,4,5,6-tetrahydrocyclopenta[d]isoxazol-6a-ol.

2. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.1 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: W a divalent unit selected from the group consisting of (W.sup.1), (W.sup.2), (W.sup.3), (W.sup.6) (W.sup.7), (W.sup.9), (W.sup.16) and (W.sup.18), and wherein the divalent unit is substituted by m radicals from the group consisting of R.sup.k and R.sup.l, and where carbon atoms bear n oxo groups: ##STR00196## R.sup.k (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (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, hydroxyl and (C.sub.1-C.sub.2)-alkoxy; R.sup.l fluorine, chlorine, bromine, iodine, cyano, hydroxyl or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl; m 0, 1, 2, 3, 4 or 5; n 0, 1 or 2;

7. The compound as claimed in claim 1, wherein the substituents have the following meaning: W a divalent unit selected from the group consisting of (W.sup.2), (W.sup.3), (W.sup.7), (W.sup.9), (W.sup.16) and (W.sup.18): ##STR00197##

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.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.

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; W a divalent unit selected from the group consisting of (W.sup.1), (W.sup.2), (W.sup.3), (W.sup.6) (W.sup.7), (W.sup.9), (W.sup.16) and (W.sup.18), and wherein the divalent unit is substituted by m radicals from the group consisting of R.sup.k and R.sup.l, and where carbon atoms bear n oxo groups: ##STR00198## 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 and CO.sub.2R.sup.e; 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, hydroxy, and (C.sub.1-C.sub.3)-alkoxy; 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; R.sup.k (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.4)-alkenyl, (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, hydroxyl and (C.sub.1-C.sub.2)-alkoxy; R.sup.l fluorine, chlorine, bromine, iodine, cyano, hydroxyl or (C.sub.1-C.sub.6)-alkoxy, (C.sub.3-C.sub.6)-alkenyloxy, (C.sub.3-C.sub.6)-alkynyloxy, each of which is substituted by m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl; 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

[0704] Chemical bonds, drawn as bars in chemical formulae, indicate the relative stereochemistry on the ring system.

Example 1

Synthesis of methyl (1S,4R)-4-[[3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-furo[3,2-d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate as a mixture of diastereoisomers

Step 1

[0705] ##STR00146##

[0706] To a mixture of 3,5-dichloro-N-hydroxy-benzimidoyl chloride (1, CAS 677727-73-0; 0.5 g) and methyl 2,3-dihydrofuran-5-carboxylate (2, CAS 70647-25-5, 1.0 g) in isopropanol (20 ml) was added sodium hydrogen carbonate (0.94 g) at 25° C., and the mixture was stirred at 50° C. for 14 hours. The mixture was concentrated under reduced pressure. The crude material was purified by reverse phase chromatography (Acetonitrile/water gradient) yielding methyl 3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-furo[3,2-d]isoxazole-6a-carboxylate 3 (400 mg, 57%). 1H NMR (400 MHz, Chloroform) 1H NMR (400 MHz, Chloroform-d) δ 7.58 (d, J=1.9 Hz, 2H), 7.44 (t, J=1.9 Hz, 1H), 4.52-4.44 (m, 1H), 4.34-4.25 (m, 1H), 3.89 (s, 3H), 3.88-3.78 (m, 1H), 2.54-2.39 (m, 1H), 2.18 (dd, J=12.8, 5.3 Hz, 1H). LC-MS [M+H].sup.+ 315.8.

Step 2

[0707] ##STR00147##

[0708] To a mixture methyl 3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-furo[3,2-d]isoxazole-6a-carboxylate (3, 385 mg) in THF/H.sub.2O (20 mL 1:1) was added lithium hydroxide (44 mg) at 25° C., and the mixture was stirred at 25° C. for 2 hours. THF was removed under reduced pressure, and the resulting mixture was extracted with methyl tert. butyl ether (MTBE, 2×5 mL). The organic phases were discarded. The aqueous phase was adjusted to pH=1, and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried (sodium sulfate) and concentrated, yielding 3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-furo[3,2-d]isoxazole-6a-carboxylate (365 mg, 99%), which was used without further purification. H NMR (400 MHz, Chloroform-d) δ 7.58 (d, J=1.9 Hz, 2H), 7.46 (t, J=1.9 Hz, 1H), 4.52-4.45 (m, 1H), 4.38-4.30 (m, 1H), 3.92-3.81 (m, 1H), 2.58-2.43 (m, 1H), 2.22 (dd, J=12.9, 5.4 Hz, 1H). (LC-MS: [M+H].sup.+ 301.6)

Step 3

[0709] ##STR00148##

[0710] To a solution of the carboxylic acid 4 (365 mg) in dimethylformamide (DMF, 3 mL) methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate 5 (196 mg, CAS 229613-83-6. HCl salt) was added. To the resulting solution was added HATU (528 mg)) and then diisopropylethylamine (0.6 mL). The resulting reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture water (10 mL) was added. The resulting mixture was extracted with ethyl acetate (3×10 mL), the combined organic layers were washed with water (3×10 mL), dried (sodium sulfate) and evaporated under reduced pressure. The crude product was purified by column chromatography using a mixture of cyclohexane:ethyl acetate (1:1) as solvent, yielding the desired product methyl (1S,4R)-4-[[3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-furo[3,2-d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate (81%, 416 mg) as a mixture of diastereoisomers. 1H NMR (400 MHz, Chloroform) δ 7.60-7.54 (m, 2H), 7.43 (t, J=1.9 Hz, 1H), 7.20-7.12 (m, 1H), 6.00-5.87 (m, 2H), 5.15-5.03 (m, 1H), 4.42-4.35 (m, 1H), 4.33-4.24 (m, 1H), 3.87-3.76 (m, 1H), 3.79-3.68 (m, 3H), 3.58-3.51 (m, 1H), 2.59-2.37 (m, 2H), 2.19-2.10 (m, 1H), 2.03-1.93 (m, 1H). LC-MS: [M+H].sup.+ 424.7.

Example 2

Synthesis of tert-butyl 3-(3,5-dichlorophenyl)-6a-[[(1R,4S)-4-methoxycarbonylcyclopent-2-en-1-yl]carbamoyl]-4,5-dihydro-3aH-pyrrolo[3,2-d]isoxazole-6-carboxylate (Cpd I,9)

[0711] ##STR00149##

[0712] In analogy to the synthesis of example 1, the synthesis of compound I.9 commenced with the cycloaddition (step 1) of 3,5-dichloro-N-hydroxy-benzimidoyl chloride (1, CAS 677727-73-0; 0.5 g, 2.23 mmol) and tert-butyl 2,3-dihydropyrrole-1-carboxylate (2, CAS 155905-79-6, 1.0 g, 4.4 mmol) under the same reaction conditions, affording 06-tert-butyl 06a-methyl 3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-pyrrolo[3,2-d]isoxazole-6,6a-dicarboxylate (3, 688 mg, 74%). LC-MS m/e (M-Boc+H).sup.+=314.8.

##STR00150##

[0713] Accordingly, compound I.9 was obtained as a mixture of diastereoisomers (800 mg, 25% yield over 2 steps) following the above described procedures. 1H NMR (400 MHz, Chloroform) δ 7.51 (d, J=5.2 Hz, 4H), 7.44 (s, 2H), 5.92 (m, 4H), 5.02 (d, J=25.8 Hz, 2H), 4.27 (d, J=8.6 Hz, 1H), 4.22 (d, J=8.9 Hz, 1H), 3.87 (s, 2H), 3.73 (s, 3H), 3.65 (s, 3H), 3.53 (s, 2H), 3.37 (m, 2H), 2.51 (m, 2H), 2.11 (m, 2H), 1.47 (m, 18H).

Example 3

Synthesis of methyl (1S,4R)-4-[3-(3,5-dichlorophenyl)-3aH,4H,5H,6H-pyrrolo[3,2-d][1,2]oxazole-6a-amido]cyclopent-2-ene-1-carboxylate (Cpd. 1.10)

[0714] ##STR00151##

[0715] A solution of tert-butyl 3-(3,5-dichlorophenyl)-6a-[[(1 R,4S)-4-methoxycarbonylcyclopent-2-en-1-yl]carbamoyl]-4,5-dihydro-3aH-pyrrolo[3,2-d]isoxazole-6-carboxylate (Cpd I, 9, 600 mg, 1.14 mmol) in a 4:1 mixture of dichloromethane and trifluoroacetic acid (10 mL) was stirred until consumption. After quenching the reaction with aq. sat. NaHCO.sub.3 (10 mL), the aqueous phase was extracted with dichloromethane (2×10 mL). The combined extracts were dried over Na.sub.2SO.sub.4, filtered and concentrated. The residue was purified by prep-HPLC (trifluoroacetic acid 0.1%, acetonitrile-water) to give methyl (1S,4R)-4-[3-(3,5-dichlorophenyl)-3aH,4H,5H,6H-pyrrolo[3,2-d][1,2]oxazole-6a-amido]cyclopent-2-ene-1-carboxylate (Cpd. 1.10, 350 mg, 72%). 1H NMR (400 MHz, Chloroform) δ 7.56 (d, J=1.9 Hz, 2H), 7.55 (d, J=1.9 Hz, 2H), 7.40 (m, 2H), 7.34 (m, 2H), 5.91 (m, 4H), 5.04 (m, 2H), 4.09 (m, 2H), 3.74 (s, 3H), 3.69 (s, 3H), 3.53 (m, 2H), 3.31 (m, 2H), 2.97 (m, 2H), 2.50 (m, 2H), 2.28 (m, 4H), 2.04 (dd, J=12.6, 5.8 Hz, 2H), 1.95 (m, 2H).

Example 4

methyl (1S,4R)-4-[[3-(3,5-dichlorophenyl)-4,5-dihydro-3aH-thieno[3,2-d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate (Cpd. 1.13)

Step 1

[0716] ##STR00152##

[0717] To a solution of 2,3-dihydrothiophene-5-carboxylic acid (1, CAS 86610-33-5, 1.0 g, 7.68 mmol) in a 3:2 mixture of toluene and methanol (20 mL) a solution of trimethylsilyl diazomethane (2 M, 5.8 mL, 11.5 mmol) was added at room temperature. After stirring for 1 h, the reaction was quenched with acetic acid (1 mL) and the mixture was concentrated to afford methyl 2,3-dihydrothiophene-5-carboxylate (0.90 g, 58%). 1H NMR (400 MHz, Chloroform) δ 6.62 (td, J=3.2, 0.6 Hz, 1H), 3.78 (d, J=0.7 Hz, 3H), 3.33 (t, J=8.8 Hz, 2H), 2.93 (td, J=8.8, 3.2 Hz, 2H).

Steps 2-4

[0718] ##STR00153##

[0719] In analogy to the synthesis of example 1, Cpd. 1.13 was obtained in 1:1 ratio of diastereomers (180 mg, 6.5% over 3 steps) as an amorphous foam. 1H NMR (400 MHz, Chloroform) δ 7.54 (d, J=1.9 Hz, 2H), 7.53 (d, J=1.8 Hz, 2H), 7.43 (m, 2H), 7.13 (m, 2H), 5.92 (m, 4H), 5.06 (m, 2H), 4.67 (d, J=2.8 Hz, 1H), 4.65 (d, J=2.8 Hz, 1H), 3.75 (s, 3H), 3.73 (s, 3H), 3.52 (m, 2H), 3.10 (m, 2H), 3.03 (m, 2H), 2.68 (m, 2H), 2.50 (m, 4H), 2.00 (dt, J=14.0, 3.7 Hz, 1H), 1.93 (dt, J=14.0, 3.7 Hz, 1H).

Example 5

Synthesis of methyl (4S)-4-[[4-(3,5-difluorophenyl)-2-oxa-3-azabicyclo[3.1.0]hex-3-ene-1-carbonyl]amino]pentanoate (Cpd 1.16)

Step 1

[0720] ##STR00154##

[0721] To a solution of 3,5-difluoro-N-hydroxy-benzimidoyl chloride (1, CAS 677728-84-6; 1.2 g, 6.26 mmol) in THF (20 mL) triethylamine (0.83 mL, 6.0 mmol) was added at −20° C. After stirring for 30 min, methy-2-(brommethyl)lmethacrylate (2, CAS 4224-69-5, 1.50 mL, 12.5 mmol) was added dropwise at the same temperature. After replacing the cold bath with an ice bath, the mixture was stirred for 16 h, while allowing the reaction to warm to room temperature. The mixture was concentrated under reduced pressure. The crude material was purified by reverse phase chromatography (Acetonitrile/water gradient) yielding methyl 5-(bromomethyl)-3-(3,5-difluorophenyl)-4H-isoxazole-5-carboxylate 3 (1.0 g, 48%). 1H NMR (400 MHz, Chloroform) δ 7.21 (m, 2H), 6.90 (tt, J=8.7, 2.3 Hz, 1H), 4.01 (d, J=17.4 Hz, 1H), 3.88 (m, 4H), 3.69 (m, 1H), 3.50 (d, J=17.4 Hz, 1H).

Step 2

[0722] ##STR00155##

[0723] To a solution of methyl 5-(bromomethyl)-3-(3,5-difluorophenyl)-4H-isoxazole-5-carboxylate (1.00 g, 2.99 mmol) in DMF (10 mL) sodium hydride (144 mg, 3.59 mmol) was added at room temperature. After stirring for 16 h, the mixture was concentrated and the residue was purified by prep-HPLC (trifluoroacetic acid 0.1%, acetonitrile-water) to give 4-(3,5-difluorophenyl)-2-oxa-3-azabicyclo[3.1.0]hex-3-ene-1-carboxylic acid (4, 400 mg, 56%). LC-MS m/e (M+H).sup.+=239.9.

Step 3

[0724] ##STR00156##

[0725] According to the procedure for the peptide coupling, step 3, in example 1, 4-(3,5-difluorophenyl)-2-oxa-3-azabicyclo[3.1.0]hex-3-ene-1-carboxylic acid (4, 240 mg, 1.00 mmol) was treated with methyl (4S)-4-aminopentanoate hydrochloride (168 mg, 1.00 mmol) to afford Cpd. 1.16 (200 mg, 57%) as a 1:1 mixture of diastereoisomers. 1H NMR (400 MHz, Chloroform) δ 7.29 (m, 4H), 6.93 (tq, J=8.7, 2.2 Hz, 2H), 6.51 (d, J=8.9 Hz, 2H), 4.13 (m, 2H), 3.71 (s, 3H), 3.64 (s, 3H), 3.22 (m, 2H), 2.43 (t, J=7.3 Hz, 2H), 2.36 (dt, J=7.9, 6.8 Hz, 2H), 2.18 (ddd, J=9.7, 5.3, 2.0 Hz, 2H), 1.88 (m, 4H), 1.27 (d, J=6.6 Hz, 3H), 1.22 (d, J=6.6 Hz, 3H), 0.82 (td, J=5.0, 2.3 Hz, 2H).

Example 6

Synthesis of methyl 4-[[3-(3,5-difluorophenyl)-3aH-furo[3,2-d]isoxazole-6a-carbonyl]amino]butanoate (Cpd 1.18)

Step 1

[0726] ##STR00157##

[0727] To a mixture of 3,5-difluoro-N-hydroxy-benzimidoyl chloride (1, CAS 677728-84-6; 3 g, 15.71 mmol) in toluene (100 ml) was added pyridine (25 ml) and methyl-2-furoat (2, CAS 611-13-2; 10 ml) in toluene (10 ml) dropwise at room temperature and the mixture was stirred at 120° C. for 4 h. The mixture was poured into H.sub.2O (200 ml), extracted with EtOAc (100 ml), washed with brine, dried over Na.sub.2SO.sub.4 concentrated and purified by prep-HPLC (acetonitrile-water) to give methyl 3-(3,5-difluorophenyl)-3aH-furo[3,2-d]isoxazole-6a-carboxylate (116 mg, 2.6%) as yellow solid. 1H NMR (400 MHz, Chloroform) δ 7.41 (m, 2H), 6.91 (tt, J=2.3, 8.7 Hz, 1H), 6.28 (d, J=9.0 Hz, 1H), 6.19 (d, J=2.8 Hz, 1H), 6.11 (m, 1H), 3.84 (s, 3H).

Step 2

[0728] ##STR00158##

[0729] According to the procedure for the saponification, step 3, in example 1, methyl 3-(3,5-difluorophenyl)-3aH-furo[3,2-d]isoxazole-6a-carboxylate (3, 107 mg, 0.38 mmol) was converted to 3-(3,5-difluorophenyl)-3aH-furo[3,2-d]isoxazole-6a-carboxylate (4, 100 mg, 98%). LC-MS m/e (M+H).sup.+=268.1.

##STR00159##

[0730] According to the procedure for the peptide coupling, step 3, in example 1, 3-(3,5-difluorophenyl)-3aH-furo[3,2-d]isoxazole-6a-carboxylate (4, 100 mg, 1.00 mmol) was treated with methyl 4-aminobutanoate hydrochloride (CAS 13031-60-2, 69 mg, 0.45 mmol) to afford Cpd. 1.18 (95 mg, 69%). 1H NMR (400 MHz, Chloroform) δ 7.40 (dt, J=6.2, 2.1 Hz, 2H), 6.92 (tt, J=8.7, 2.3 Hz, 1H), 6.72 (s, 1H), 6.28 (d, J=8.9 Hz, 1H), 6.16 (d, J=2.8 Hz, 1H), 6.08 (dd, J=8.9, 2.8 Hz, 1H), 3.64 (s, 3H), 3.37 (m, 2H), 2.39 (m, 2H), 1.88 (m, 2H).

Example 7

Synthesis of methyl (1S,4R)-4-[[3-(3,5-difluorophenyl)-3a,4-dihydrocyclopenta[d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate (Cpd 1.19)

Step 1

[0731] ##STR00160##

[0732] The mixture of 2,5-dimethoxytetrahydrofuran (1, CAS 696-59-3 13.2 g, 100 mmol) in HCl (0.6N, 80 mL) was stirred at 70° C. for 3 h. After cooling to 0° C., the mixture was neutralized with 10% KHCO.sub.3 solution. After addition of methyl 2-dimethoxyphosphorylacetate (2, 18.2 g, 100 mL) and an aqueous solution of K.sub.2CO.sub.3 (6.4N, 32 mL) was added. The mixture was stirred at 20° C. for 2 days. The reaction was extracted with EtOAc (150 mL*2). The combined organics were washed with brine, dried and concentrated. The crude was purified by column chromatography (EtOAc/PE=0% to 100%) to give methyl 5-hydroxycyclopentene-1-carboxylate (3, 5.5 g, 38.7%) as yellow oil. 1H NMR (400 MHz, Chloroform) δ 6.92 (t, J=2.4 Hz, 1H), 5.10 (m, 1H), 3.78 (m, 3H), 2.65 (m, 1H), 2.36 (m, 2H), 1.87 (m, 1H).

Step 2

[0733] ##STR00161##

[0734] In analogy to step 1 in example 5, to a mixture of methyl 5-hydroxycyclopentene-1-carboxylate (3, 6 g, 41.8 mmol) and 3,5-difluoro-N-hydroxy-benzimidoyl chloride (4, CAS 677728-84-6; 4 g, 20.9 mmol) in toluene (40 ml) was added triethylamine (46 g, 20.9 mmol) at 20° C. The mixture was stirred at 20° C. for 2 h. The reaction was quenched with H.sub.2O (100 mL) and extracted with EtOAc (2×100 mL). The combined extracts were washed with brine, dried and concentrated. The crude was purified by prep-HPLC (trifluoroacetic acid 0.1%, acetonitrile-water) to give methyl 3-(3,5-difluorophenyl)-6-hydroxy-3a,4,5,6-tetrahydrocyclopenta[d]isoxazole-6a-carboxylate (5, 755 mg, 12%) as yellow solid. LC-MS m/e (M+H).sup.+=298.0.

Step 3

[0735] ##STR00162##

[0736] To a mixture of methyl 3-(3,5-difluorophenyl)-6-hydroxy-3a,4,5,6-tetrahydrocyclopenta[d]isoxazole-6a-carboxylate (5, 555 mg, 1.87 mmol) in dichloromethane (10 mL) and pyridine (591 mg, 7.48 mmol) was added triflic anhydride (791 mg, 12.8 mmol) at −78° C. dropwise. The mixture was stirred at −78° C. for 4 h. The mixture was quenched with H.sub.2O (15 mL) and extracted with dichloromethane (2×15 mL). The combined organics were washed with brine, dried and concentrated to give the methyl 3-(3,5-difluorophenyl)-3a,4-dihydrocyclopenta[d]isoxazole-6a-carboxylate (6, 522 mg, quantitative) as a yellow oil. 1H NMR (400 MHz, Chloroform) δ 7.94 (tt, J=1.7, 7.7 Hz, 1H), 7.52 (m, 2H), 4.63 (d, J=9.2 Hz, 1H), 4.38 (d, J=8.4 Hz, 1H), 3.85 (s, 3H), 2.51 (m, 2H).

Step 4

[0737] ##STR00163##

[0738] According to the procedure for the saponification, step 3, in example 1, methyl 3-(3,5-difluorophenyl)-3a,4-dihydrocyclopenta[d]isoxazole-6a-carboxylate (6, 133 mg,) was converted to 3-(3,5-difluorophenyl)-3a,4-dihydrocyclopenta[d]isoxazole-6a-carboxylate (7, 125 mg, quantitative). LC-MS m/e (M+H).sup.+=266.1.

Step 5

[0739] ##STR00164##

[0740] According to the procedure for the peptide coupling, step 3, in example 1, 3-(3,5-difluorophenyl)-3a,4-dihydrocyclopenta[d]isoxazole-6a-carboxylate (7, 125 mg, 0.47 mmol) was treated with [(1R,4S)-4-methoxycarbonylcyclopent-2-en-1-yl]ammonium; chloride (100 mg, 0.46 mmol) to afford Cpd. 1.19 (126 mg, 69%) as a 1:1 mixture of diastereoisomers. 1H NMR (400 MHz, Chloroform) δ 7.20 (m, 6H), 6.88 (m, 2H), 6.13 (m, 2H), 5.89 (m, 6H), 5.08 (m, 2H), 4.39 (m, 2H), 3.75 (s, 3H), 3.72 (s, 3H), 3.54 (m, 2H), 3.10 (m, 2H), 2.63 (m, 2H), 2.52 (m, 2H), 1.99 (dt, J=14.0, 3.9 Hz, 1H), 1.93 (dt, J=13.9, 3.9 Hz, 1H).

Example 8

Synthesis of methyl (1S,4R)-4-[[3-(3,5-dichlorophenyl)-5,6-dihydro-3aH-furo[2,3-d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate (Cpd. 1.25)

[0741] ##STR00165##

[0742] In analogy to the synthesis of example 1, the synthesis of compound I.25 commenced with the cycloaddition (step 1) of 3,5-dichloro-N-hydroxy-benzimidoyl chloride (1, CAS 677727-73-0; 1.0 g, 4.45 mmol) and ethyl-2,3-dihydro-4-furoate (2, CAS 53750-82-6, 1.0 g, 7.0 mmol) following the same sequence, affording methyl (1S,4R)-4-[[3-(3,5-dichlorophenyl)-5,6-dihydro-3aH-furo[2,3-d]isoxazole-6a-carbonyl]amino]cyclopent-2-ene-1-carboxylate (Cpd. 1.25, 680 mg, 36% over 3 steps) as a 1:1 mixture of diastereoisomers. 1H NMR (400 MHz, Chloroform) δ 7.61 (d, J=1.8 Hz, 2H), 7.57 (d, J=1.8 Hz, 2H), 7.42 (t, J=1.9 Hz, 1H), 7.40 (t, J=1.8 Hz, 1H), 6.47 (m, 2H), 6.24 (s, 1H), 6.17 (s, 1H), 5.89 (m, 4H), 5.10 (t, J=8.4 Hz, 1H), 5.04 (t, J=8.1 Hz, 1H), 4.23 (dd, J=8.9, 7.6 Hz, 2H), 3.72 (m, 2H), 3.62 (s, 3H), 3.60 (s, 3H), 3.46 (m, 2H), 3.03 (m, 2H), 2.33 (m, 2H), 2.23 (ddd, J=12.9, 10.3, 4.9 Hz, 2H), 1.92 (m, 1H), 1.63 (m, 1H).

[0743] 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).

[0744] In analogy to the examples described above, the following compounds of formula (I) were prepared, starting from commercially available compounds:

TABLE-US-00002 TABLE 2 Cpd HPLC/MS I1 [00166] 422.8 I2 [00167] 412.7 I3 [00168] 391   I4 [00169] 472.7 I5 [00170] 440.7 I6 [00171] 408.7 I7 [00172] 410.5 I8 [00173] 424.7 I9 [00174] 569.0 I10 [00175] 423.7 I11 [00176] 438.2 I12 [00177] 450.8 I13 [00178] 440.0 I14 [00179] 408.7 I15 [00180] 398.8 I16 [00181] 353.0 I17 [00182] 394.7 I18 [00183] 367.2 I19 [00184] 389.2 I20 [00185] 412.9 I21 [00186] 410.9 I22 [00187] 428.9 I23 [00188] 400.9 I24 [00189] 414.9 I25 [00190] 425.0 HPLC/MS = MassChargeRatio

B USE EXAMPLES

[0745] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0746] 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.

[0747] 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.

[0748] 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.

[0749] 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.

[0750] The test plants used in the greenhouse experiments were of the following species:

TABLE-US-00003 Bayer code Scientific name ABUTH Abutilon theophrasti ALOMY Alopercurus myosuroides AMARE Amaranthus retroflexus APESV Apera spica-venti AVEFA Avena fatua ECHCG Echinocloa crus-galli POLCO Fallopia convolvulus SETFA Setaria faberi SETVI Setaria viridis

[0751] At an application rate of 0,500 kg/ha, applied by the pre-emergence method: [0752] compound I15 showed good herbicidal activity against APESV.

[0753] At an application rate of 0,250 kg/ha, applied by the pre-emergence method: [0754] compounds I10, I13 showed very good herbicidal activity against AMARE. [0755] compounds I9, I18 showed good herbicidal activity against AMARE. [0756] compounds I13, I17, I19 showed very good herbicidal activity against APESV. [0757] compounds I10, I16 showed good herbicidal activity against APESV. [0758] compound I13 showed very good herbicidal activity against ECHCG. [0759] compound I19 showed very good herbicidal activity against SETFA.

[0760] At an application rate of 0.125 kg/ha, applied by the pre-emergence method: [0761] compound I1 showed very good herbicidal activity against AMARE. [0762] compounds I2, I12 showed good herbicidal activity against AMARE. [0763] compound I1 showed very good herbicidal activity against APESV. [0764] compound I2 showed good herbicidal activity against APESV. [0765] compound I12 showed good herbicidal activity against SEFTA.

[0766] At an application rate of 0.500 kg/ha, applied by the post-emergence method: [0767] compound I15 showed good herbicidal activity against ABUTH. [0768] compound I15 showed very good herbicidal activity against SETVI. [0769] compound I15 showed very good herbicidal activity against AVEFA.

[0770] At an application rate of 0.250 kg/ha, applied by the post-emergence method: [0771] compounds I10, I16, I17, I19 showed very good herbicidal activity against ALOMY. [0772] compounds I10, I13, I16, I17, I19 showed very good herbicidal activity against AVEFA. [0773] compounds I13, I19 showed good herbicidal activity against ABUTH. [0774] compounds I13, I17 showed very good herbicidal activity against SETVI.

[0775] At an application rate of 0.125 kg/ha, applied by the post-emergence method: [0776] compounds I1, I12 showed good herbicidal activity against ABUTH. [0777] compound I2 showed very good herbicidal activity against ALOMY. [0778] compound I1 showed good herbicidal activity against ALOMY. [0779] compound I1 showed very good herbicidal activity against AMARE. [0780] compound I2 showed good herbicidal activity against AMARE. [0781] compound I2 showed very good herbicidal activity against AVEFA. [0782] compound I1 showed good herbicidal activity against AVEFA. [0783] compounds 11, 12 showed very good herbicidal activity against ECHCG. [0784] compounds 11, 12 showed good herbicidal activity against SETVI.

[0785] At an application rate of 0.63 kg/ha, applied by the post-emergence method: [0786] compound I20 showed very good herbicidal activity against SETVI. [0787] compound I21 showed very good herbicidal activity against AMARE. [0788] compound I20 showed very good herbicidal activity against AVEFA. [0789] compound I21 showed good herbicidal activity against AVEFA. [0790] compound I20 showed good herbicidal activity against ECHCG. [0791] compound I21 showed good herbicidal activity against POLCO.