Herbicidal benzoxazinones
The present invention relates to benzoxazinones of the general formula (I) wherein the variables are defined according to the description, processes and intermediates for preparing the benzoxazinones of the formula (I), compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one benzoxazinones of the formula (I) to act on plants, their seed and/or their habitat.
1. A compound of formula I:
wherein
R 1 is hydrogen or halogen;
R 2 is halogen;
R 3 is hydrogen or halogen;
R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl;
R 5 is hydrogen, NH 2 , C 1 -C 6 -alkyl or C 3 -C 6 -alkynyl;
R 6 is hydrogen or C 1 -C 6 -alkyl; and
W is O or S; and
Z is O or S.
2. The compound of claim 1 wherein R 1 and R 3 are halogen.
3. The compound of claim 1 wherein R 5 and R 6 are independently of one another C 1 -C 4 -alkyl.
4. The compound of claim 2 wherein R 5 and R 6 are independently of one another C 1 -C 4 -alkyl.
5. The compound of claim 1 which is of formula I.a
6. Process for the preparation of the compound of claim 1 comprising reacting a compound of formula IV.d:
with a compound of formula III:
to form a compound of formula IV.e:
and cyclizing the compound of formula IV.e to form the compound of claim 1 .
7. An herbicidal composition comprising an herbicidally active amount of at least one compound of claim 1 , at least one inert liquid and/or solid carrier and optionally at least one surface-active substance.
8. A composition for the desiccation or defoliation of plants, comprising at least one compound of claim 1 in an amount effective to act as a desiccant or defoliant, at least one inert liquid and/or solid carrier and optionally at least one surface-active substance.
9. A method of controlling undesired vegetation, which comprises treating plants, their environment or seed with an herbicidally active amount of at least one compound of claim 1 .
10. The method of claim 9 , wherein R 1 and R 3 of the compound are halogen.
11. The method of claim 9 , wherein R 5 and R 6 of the compound are independently of one another C 1 -C 4 -alkyl.
12. The method of claim 9 , wherein R 1 and R 3 of the compound are halogen and R 5 and R 6 are independently of one another C 1 -C 4 -alkyl.
13. The method of claim 9 , wherein the compound is of formula I.a
wherein
R 1 is halogen;
R 3 is halogen; and
R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl.
14. A method for the desiccation or defoliation of a plant, which comprises treating a plant with at least one compound of claim 1 in an amount effective to desiccate or defoliate the plant.
15. The method of claim 14 , wherein R 1 and R 3 of the compound are halogen.
16. The method of claim 14 , wherein R 5 and R 6 of the compound are independently of one another C 1 -C 4 -alkyl.
17. The method of claim 14 , wherein R 1 and R 3 of the compound are halogen and R 5 and R 6 of the at least one compound are independently of one another C 1 -C 4 -alkyl.
18. The method of claim 14 , wherein the compound is of formula I.a
wherein
R 1 is halogen;
R 3 is halogen; and
R 4 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 -haloalkynyl, C 1 -C 6 -alkoxy or C 3 -C 6 -cycloalkyl-C 1 -C 6 -alkyl.
19. An herbicidal composition comprising a herbicidal active amount of at least one compound of claim 1 and at least one further active compound selected from the group consisting of herbicides B and safeners C, wherein said herbicides B is selected from the group consisting of herbicides of class b1) to b)15:
b1) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitose inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b11) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxin herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol and its salts and esters; and
wherein said safener C is selected from the group consisting of benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine.
20. The compound of claim 1 , wherein the compound is