DIOXAZOLINES AND THEIR USE AS HERBICIDES.

Abstract

The invention relates to compounds of Formula (I), (see Formula) (I) and their use as herbicides. In said formula, R1 to R7 represent groups such as hydrogen, halogen, or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; X is a bond or a divalent unit; and Y is hydrogen, cyano, hydroxyl, or a linear or cyclic organic group. The invention also relates to a composition comprising such compounds and its use for controlling unwanted vegetation.

Claims

1. Compounds of Formula (I) 1 1 and 1 or where the substituents have the following meanings: R1 hydrogen, (C3-C4)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-haloalkyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C3-C4)-alkoxy-(C3-C4)-alkyl, (C3-C4)-alkoxy, (C3-C4)-haloalkoxy; R2 hydrogen, halogen, hydroxyl, cyano, (C3-C4)-alkyl, (C3-C4)-haloalkyl, (C3-C4)-alkoxy, (C3-C3)-haloalkoxy; R3 hydrogen, halogen, nitro, hydroxyl, cyano, (C3-C3)-alkyl, (C3-C3)-haloalkyl, hydroxy(C3-C3)-alkyl, (C3-C5-cycloalkyl, (C3-C5-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C3-C3)-alkoxy, (C3-C3)-haloalkoxy, (C3-C5-alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-C3)-alkyl, (C1-C3)alkylsulfinyl, (Ci-Csj-alkylsulfonyl;R4 hydrogen, halogen, hydroxyl, cyano, (C3-C4)-alkyl, (C3-C4)-haloalkyl, (C3-C4)-halocycloalkyl, (C3-C4)-alkoxy, (C2-C3)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl, (C3-C4)-alkylthio; R5 hydrogen, halogen, nitro, hydroxyl, cyano, (C3-C4)-alkyl, (C3-C4)-haloalkyl, hydroxy(C3-C4)-alkyl, (C3-C5)-cycloalkyl, (C3-C4)-halocycloalkyl, hydroxy-(C3-C5)-cycloalkyl, (C3-C4)-alkoxy, (C3-C4)-haloalkoxy, (Ci-Cs / alkoxycarbonyl, (C2-C3)-alkenyl, (C2-C3)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C1-Csj-alkylthio, (C1-C3)alkylsulfinyl, (Ci-Csj-alkylsulfonyl; R6 hydrogen, halogen, hydroxyl, cyano, (Ci-Csj-alkyl, (Ci-Csj-haloalkyl, (Ci-Csj-alkoxy, (Ci-Csj-haloalkoxy; R7 fluorine, cyano or (Ci-Csj-alkyl, (Cs-Csj-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C1Csj-alkoxy, each substituted with m radicals of the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl, cyano and (Ci-Cej-alkoxy;X a bond (Xo) or a divalent unit of the group consisting of (X1), (X2), (X3), (X4), (X5) and (X6): (X1) (*) ML / a / zuzz / u 11 and 1 or R8-R13 each independently, hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl, cyano, CO2R®, CONRbRd, NRbCO2Re, Ra or (Ci-Ce)-alkyl, (C3-C5)-cycloalkyl, (C2-Ce)-alkenyl, (C2-C6)-alkynyl, each substituted with radicals of the group consisting of fluorine, chlorine, bromine, iodine, hydroxyl and cyano, or (Ci-CeJ-alkoxy, (C3-C6)-cycloalkoxy, (Cs-Ce)alkenyloxy, (C3-C6)-alkynyloxy, (C1-C3)-alkylthio, (C1-C3)-alkylsulfinyl, (C1-C3)alkylsulfonyl, each substituted with m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano and (C1-C2)-alkoxy;And hydrogen, cyano, hydroxyl, Z, or (Ci-Ci2)-alkyl, (Cs-Csj-cycloalkyl, (C2-Ci2)-alkenyl or (C2-Ci2)-alkynyl, each substituted with m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, ORd, Z, OZ, NHZ, S(O)nRa, SO2NRbRd, SO2NRbCORe, CO2Re, CONRbRh, CORb, CONR®SO2Ra, NRbR®, NRbCOR®, NRbCONR®R®, NRbCO2R®, NRbSO2R® NRbSO2NRbR®, OCONRbR®, OCSNRbR®, POR'R' and C(Rb)=NOR®; Z a saturated, partially unsaturated, fully unsaturated or aromatic ring of 3, 4, 5 or 6 members, except phenyl, which is formed from r carbon atoms, n nitrogen atoms, n sulfur atoms and n oxygen atoms, and which is substituted with m radicals of the group consisting of CO2R®, CONRbRh, S(O)rRa, SO2NRbRd, SO2NRbCOR®, CORb, CONR®SO2Ra, NRbRe, NRbCOR®, NRbCONReR®, NRbCO2R®, NRbSO2R®, NRbSO2NRbR®, OCONRbR®, OCSNRbR®, PORfRf, C(Rb)=NOR®, Rb, Rc, R® and Rf, and wherein the sulfur atoms and the carbon atoms have n oxo groups;Ra (C3-C6)-alkyl or (C3-C6)-cycloalkyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl and (C3-C4)-alkoxy; Rb hydrogen, (C3-C6)-alkoxy or Ra; Rc fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa or (C3-C6)-alkoxy, (C3-C6)-alkenyloxy or (C3-C6)-alkynyloxy, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (C3-C2)-alkoxy; Rd hydrogen or (C3-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (Cs-C6)-cycloalkyl-(CiC3)-alkyl, phenyl-(Ci-C3)-alkyl, furanyl-(Ci-C3)-alkyl or (C2-C4)-alkynyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra, CONRbRh, (Ci-C2)-alkoxy, (Ci-Cs)-alkylthio, (Ci-C3)-alkylsulfonyl, (Ci-C3)-alkylsulfonyl, phenylthio, phenylsulfinyl and phenylsulfonyl; Re Rd; Rf (Ci-C3)-alkyl or (Ci-C3)-alkoxy;Rh hydrogen or (Ci-CeJ-alkyl, (Ci-C2)-alkoxy, (Cs-CeJ-cycloalkyl, (C2-C4)-alkenyl, (Ci-Ce)alkoxycarbonyl-(Ci-C6)-alkyl or (C2-C4)-alkynyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano, CO2Ra and (Ci-C2)-alkoxy; m 0, 1, 2, 3, 4 or 5; n 0, 1 or 2; r 1, 2, 3, 4 or 6; including their salts, amides, esters or thioesters acceptable in agriculture, provided that 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 compounds according to claim 1, wherein the substituents have the following meanings: R1 hydrogen.

3. The compounds according to claim 1 or 2, wherein the substituents have the following meanings: R2 hydrogen, halogen, (C3-Ci)-alkyl; R6 hydrogen, halogen, (C3-Ci)-alkyl.

4. The compounds according to any of claims 1 to 3, wherein the substituents have the following meanings: R3 hydrogen, halogen, hydroxyl, cyano, (C3-Ci)-alkyl; R5 hydrogen, halogen, hydroxyl, cyano, (C3-Ci)-alkyl.

5. The compounds according to any of claims 1 to 4, wherein the substituents have the following meanings: R4 hydrogen, halogen.

6. The compounds according to any of claims 1 to 5, wherein the substituents have the following meanings: R7 (C3-C)-alkyl, (C3-C4)-cycloalkyl, (C2-C3)-alkenyl, (C3-C)-alkoxy, each substituted with m radicals of the group consisting of fluorine, chlorine and (C2-C)-alkoxy.

7. The compounds according to any one of claims 1 to 5, wherein the substituents have the following meanings: R7 (C1-C2)-alkyl, cyclopropyl, (C1-C2)-haloalkyl, (C2-C3)-alkenyl, (C1-C2)-alkoxy.

8. The compounds according to any of claims 1 to 7, wherein the substituents have the following meanings: X a bond.

9. The compounds according to any of claims 1 to 8, wherein the substituents have the following meanings: X a bond; Y (Ci-CsJ-alkyl, (Cs-Cej-cycloalkyl, (Cz-Csj-alkenyl or (Cz-Csj-alkynyl, each substituted with m radicals from the group consisting of fluorine, chlorine, bromine, iodine, cyano, hydroxyl, ORd, Z, OZ, NHZ, S(O)nRa, SO2NRbRd, SO2NRbCORe, CO2Re, CONRbRh, CORb, CONReSO2Ra, NRbRe, NRbCOR®, NRbCONReRe, NRbCO2Re, NRbSO2R® NRbSO2NRbRe, OCONRbRe, OCSNRbRe, PORfRf and C(Rb)=NORe.

10. The compounds according to any one of claims 1 to 8, wherein the substituents have the following meanings: X a bond; YZ; Z a saturated or partially unsaturated 4- or 5-membered ring formed from r carbon atoms, yn oxygen atoms, each substituted with m radicals from the group consisting of CO2Re, CONRbRh, CONReSO2Ra, Rb, Rc, Re and RL 11. The compounds according to claim 1, wherein the substituents have the following meanings: R1 hydrogen, (C3-C4)-alkyl, (C3-C4)-cycloalkyl, (C3-C4)-haloalkyl, (C2-C3)-alkenyl, (C2-C4)-haloalkenyl, (C2-C3)-alkynyl, (C2-C3)-haloalkynyl, (C3-C4)-alkoxy, (C3-C4)-alkyl, (C3-C4)-alkoxy, (C3-C4)-haloalkoxy; R2 hydrogen, halogen, (C3-C4)-alkyl, (C3-C4)-haloalkyl, (C3-C4)-alkoxy, (C3-C4)-haloalkoxy; R3 hydrogen, halogen, hydroxyl, cyano, (C3-C5)-alkyl, (C3-C5)-haloalkyl, (C3-C5)-halocycloalkyl, (C3-C5)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R4 hydrogen, halogen, hydroxyl, cyano, (C3-C5)-alkyl, (C3-C5)-haloalkyl, (C3-C4)-halocycloalkyl, (C3-C5)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl; R5 hydrogen, halogen, hydroxyl, cyano, (C3-C5)-alkyl, (C3-C5)-halocycloalkyl, (C3-C5)-haloalkoxy, (C2-C3)-haloalkenyl, (C2-C3)-haloalkynyl;R6 hydrogen, halogen, (C1-C2)-alkyl, (C1-C3)-haloalkyl, (C1-C3)-alkoxy, (C1-C3)-haloalkoxy; R7 (C1-C2)-alkyl, cyclopropyl, (C1-C2)-haloalkyl, (C2-C3)-alkenyl, (C1-C2)-alkoxy; X a bond; YZ or (C1-C2)-alkyl, (C1-C2)-cycloalkyl, (C2-C3)-alkenyl or (C2-C2)-alkynyl, each substituted with m radicals from the group consisting of fluorine, CO2Re and CONReSO2Ra; Z saturated or partially unsaturated 4- to 5-membered ring formed from r carbon atoms, n oxygen atoms, and substituted with m radicals from the group consisting of C2Re, CONRbRh, CONReSO2Ra, Rb, Rc, Re and Rf; Ra (C3-C6)-alkyl or (C3-C6)-cycloalkyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl; Rb hydrogen or (O-C6)-alkyl or (C3-C6)-cycloalkyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, iodine, cyano and hydroxyl;Rc fluorine, chlorine, bromine, iodine, cyano, hydroxyl, S(O)nRa or (Ci-C6)-alkoxy, (Cs-Cs1)-alkenyloxy or (Cs-Cs1)-alkynyloxy, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (Ci-C2)-alkoxy; Re hydrogen or (Ci-Ce)-alkyl, (Cs-Ce1)-cycloalkyl, (C2-C4)-alkenyl, phenyl-(Ci-C3)-alkyl or (C2-C4)-alkynyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (Ci-C2)-alkoxy; Rf (Ci-C3)-alkyl or (Ci-C3)-alkoxy; Rh hydrogen or (Ci-C6-alkyl, (C3-C6)-cycloalkyl, (C2-C4)-alkenyl, (Ci-C6)-alkoxycarbonyl, (Ci-C6)-alkyl or (C2-C4)-alkynyl, each of which is substituted with m radicals selected from the group consisting of fluorine, chlorine, bromine, cyano and (Ci-C2)-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 according to any one of claims 1 to 11, and at least one auxiliary, which is common in the formulation of compounds for crop protection.

13. The composition according to claim 12, comprising another herbicide.

14. The use of a compound according to any of claims 1 to 11 or of the composition according to claim 12 or 13 for controlling unwanted vegetation.

15. A method for controlling unwanted vegetation, comprising enabling an herbicide-effective amount of at least one compound according to any one of claims 1 to 11 or of the composition according to claim 12 or 13 to act on plants, their seeds and / or their habitat.