DIOXAZOLINES AND THEIR USE AS HERBICIDES

Abstract

The invention relates to compounds of formula (I), (I) and their use as herbicides. In said formula, R.sup.1 to R.sup.7 represent groups such as hydrogen, halo-gen 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) ##STR00239## 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 fluorine, cyano, or (C.sub.1-C.sub.6)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.1-C.sub.6)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and (C.sub.1-C.sub.6)-alkoxy; X a bond (X.sup.1) 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): ##STR00240## R.sup.8-R.sup.13 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, 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, 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; 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 5-methyl-3-phenyl-1,4,2-dioxazole-5-carboxamide.

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: R.sup.7 (C.sub.1-C.sub.3)-alkyl, (C.sub.3-C.sub.4)-cycloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.1-C.sub.3)-alkoxy, each substituted by m radicals from the group consisting of fluorine, chlorine, and (C.sub.1-C.sub.2)-alkoxy.

7. The compound as claimed in claim 1, wherein the substituents have the following meaning: R.sup.7 (C.sub.1-C.sub.2)-alkyl, cyclopropyl, (C.sub.1-C.sub.2)-haloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.1-C.sub.2)-alkoxy.

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; R.sup.7 (C.sub.1-C.sub.2)-alkyl, cyclopropyl, (C.sub.1-C.sub.2)-haloalkyl, (C.sub.2-C.sub.3)-alkenyl, (C.sub.1-C.sub.2)-alkoxy; X a bond; Y Z, or (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.6)-alkenyl or (C.sub.2-C.sub.6)-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 which comprises allowing an herbicidally effective amount of at least one compound as claimed in claim 1, or to act on plants, their seed, and/or their habitat.

Description

A CHEMISTRY EXAMPLES

[0588] Chemical bonds, drawn as bars in chemical formulae, indicate the relative stereochemistry on the ring system.

EXAMPLES

Example 1: Synthesis of methyl (3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carbonyl]amino]butanoate (Cpd. 13)

Step 1

[0589] ##STR00222##

[0590] To a mixture of (1Z)-3,5-dichloro-N-hydroxy-benzimidoyl chloride (CAS 677727-73-0; 3 g, 13.33 mmol) in toluene (50 ml) and methyl 3,3,3-trifluoro-2-oxo-propanoate (10.4 g, 66.66 mmol) was added triethylamine (1.36 g, 13.33 mmol) in toluene (20 ml) dropwise at 25° C. and the mixture was stirred at 25° C. for 5 hours. The mixture was poured into water and extracted with ethylacetate. The combined organic layers were washed with brine, dried and concentrated. The crude material was purified by column chromatography (petrolether:ethylacetate=100:1 to 10:1) to give methyl 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylate (3.6 g, 82%) as yellow oil.

[0591] .sup.1H NMR (400 MHz, CDCl3): δ 7.73 (d, J=1.88 Hz, 2H) 7.57 (t, J=1.82 Hz, 1H) 3.99 (s, 3H)

Step 2

[0592] ##STR00223##

[0593] To a mixture of methyl 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylate (1 g, 3.31 mmol) in THF/H.sub.2O (12 ml/4 ml) was added lithium hydroxide (278 mg, 6.62 mmol) at 25° C. and the mixture was stirred at 25° C. for 2 hours. The mixture was poured into water, the pH adjusted to pH=3, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) yielded 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylic acid (700 mg, 64%) as white solid. .sup.1H NMR (400 MHz, CDCl3): δ 7.94 (t, J=1.82 Hz, 1H) 7.73 (d, J=1.88 Hz, 2H)

Step 3

[0594] ##STR00224##

[0595] To a mixture of 3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carboxylic acid (1.1 g, 3.37 mmol) in dichloromethane (20 ml) was added dimethylformamide (1 drop) and (COCl).sub.2 (641.35 mg, 5.05 mmol) at 25° C. The mixture was stirred at 25° C. for 1 hour. The mixture was concentrated, dissolved in dichloromethane (5 mL) and added to methyl (3S)-3-aminobutanoate hydrochloride (834 mg, 5.05 mmol) in pyridine (22 ml) at 0° C. dropwise. The resulting mixture was stirred at 25° C. for 2 hours. The mixture was poured into water and extracted with ethylacetate. The combined organics were washed with brine, dried and concentrated. Purification by preparative HPLC (trifluoroacetic acid, acetonitrile-water) yielded methyl (3S)-3-[[3-(3,5-dichlorophenyl)-5-(trifluoromethyl)-1,4,2-dioxazole-5-carbonyl]amino]butanoate (130 mg, 9%) as white solid. .sup.1H NMR (400 MHz, CDCl3): δ 7.75 (t, J=1.7 Hz, 2H), 7.57 (s, 1H), 7.52-7.40 (m, 1H), 4.49-4.34 (m, 1H), 3.75-3.69 (m, 3H), 2.69-2.53 (m, 2H), 1.35-1.30 (in, 3H)

[0596] 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).

[0597] In analogy to the examples described above, the following compounds of formula (I), wherein R.sup.1 is hydrogen, were prepared, starting from commercially available diesters and using commercially available amines:

##STR00225##

TABLE-US-00002 TABLE 2 Cpd. R.sup.2 R.sup.3 R.sup.4 R.sup.5 R.sup.6 R.sup.7 N*-X-Y HPLC/MS I1 H Cl H Cl H CH.sub.3 [00226] 374.8 I2 H Cl H Cl H CH.sub.3 [00227] 374.9 I3 H Cl H Cl H CF.sub.3 [00228] 428.7 I4 H F H F H CH.sub.3 [00229] 342.9 I5 H F H F H CH.sub.3 [00230] 369.0 I6 H F H F H CH.sub.3 [00231] 354.8 I7 H Cl H Cl H CH.sub.3 [00232] 360.9 I8 H F H F H CH.sub.3 [00233] 366.8 I9 H Cl H Cl H CF.sub.3 [00234] 452.9 I10 H Cl H Cl H CHCH.sub.2 [00235] 387.0 I11 H Cl H Cl H CHCH.sub.2 [00236] 410.8 I12 H Cl H Cl H OCH.sub.2CH.sub.3 [00237] I13 H Cl H Cl H OCH.sub.3 [00238] HPLC/MS = MassChargeRatio

B USE EXAMPLES

[0598] The herbicidal activity of the compounds of formula (I) was demonstrated by the following greenhouse experiments:

[0599] 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.

[0600] 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.

[0601] 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.

[0602] 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 80 to 90 and a very good herbicidal activity is given at values of 90 to 100.

[0603] The test plants used in the greenhouse experiments were of the following species:

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

[0604] At an application rate of 1,000 kg/ha, applied by the pre-emergence method: [0605] compounds 17, 18, 110 showed very good herbicidal activity against APESV. [0606] compound 18 showed very good herbicidal activity against AMARE. [0607] compound 110 showed good herbicidal activity against AMARE. [0608] compounds 18, 110 showed very good herbicidal activity against ECHCG. [0609] compound 17 showed good herbicidal activity against ECHCG. [0610] compound 17 showed very good herbicidal activity against SETFA.

[0611] At an application rate of 0,500 kg/ha, applied by the pre-emergence method: [0612] compound 13, showed very good herbicidal activity against AMARE. [0613] compound 12 showed good herbicidal activity against APESV. [0614] compounds 11, 13, 14, 15, 16 showed very good herbicidal activity against APESV. [0615] compounds 11, 14, 15, 16 showed very good herbicidal activity against ECHCG.

[0616] At an application rate of 0,250 kg/ha, applied by the pre-emergence method: [0617] compounds 19, 111 showed very good herbicidal activity against APESV. [0618] compounds 19, 111 showed good herbicidal activity against AMARE. [0619] compound 111 showed very good herbicidal activity against ECHCG.

[0620] At an application rate of 1,000 kg/ha, applied by the post-emergence method: [0621] compounds 17, 18, 110 showed very good herbicidal activity against ECHCG. [0622] compounds 17, 18 showed very good herbicidal activity against AMARE. [0623] compound 110 showed good herbicidal activity against AMARE. [0624] compounds 17, 18, 110 showed very good herbicidal activity against SETVI.

[0625] At an application rate of 0,500 kg/ha, applied by the post-emergence method: [0626] compounds 11, 12, 14, 15, 16 showed very good herbicidal activity against ALOMY. [0627] compound 13 showed good herbicidal activity against ALOMY. [0628] compounds 13, 14, 15, 16 showed very good herbicidal activity against AVEFA. [0629] compound 12 showed good herbicidal activity against AVEFA. [0630] compound 11 showed very good herbicidal activity against ECHCG. [0631] compound 16 showed very good herbicidal activity against SETVI. [0632] compounds 11, 12, 13, 14, 15 showed good herbicidal activity against SETVI.

[0633] At an application rate of 0,250 kg/ha, applied by the post-emergence method: [0634] compounds 19, 111 showed very good herbicidal activity against ALOMY. [0635] compound 19 showed very good herbicidal activity against AVEFA. [0636] compound 111 showed very good herbicidal activity against ECHCG. [0637] compounds 19, 111 showed very good herbicidal activity against SETVI.