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 method for controlling weeds in a crop area, comprising
(a) applying to herbicide-tolerant crop plants and to weeds in said area an herbicidal composition comprising an herbicidal benzoxazinone 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;
W is O or S; and
Z is O or S;
or
(b) applying to said area an herbicide-tolerant crop seed that has been treated with an herbicidal composition comprising said herbicidal benzoxazinone of formula (I);
the composition of (a) or (b) comprising an herbicidally effective amount of said benzoxazinone of formula (I).
2. The method according to claim 1 , wherein step (a) is performed by applying the composition to the crop area prior to emergence of the crop plants in said area.
3. The method according to claim 1 wherein the benzoxazinone is a benzoxazinone of formula (I.a)
wherein
R 1 is hydrogen or halogen;
R 3 is hydrogen or fluorine; and
R 4 is C 3 -C 5 -alkynyl, C 3 -C 5 -halolkynyl, or C 3 -C 5 -cycloalkyl-C 1 -C 5 -alkyl-alkyl.
4. The method according to claim 1 , wherein the benzoxazinone is a benzoxazinone of formula (I.a.35)
5. The method according to claim 1 , wherein the crop is resistant to a protoporphyrinogen-IX oxidase (PPO)-inhibitor herbicide.
6. The method according to claim 1 , wherein the crop comprises corn, wheat, sunflower, sugarcane, cotton, rice, canola, oilseed rape, or soybean.
7. The method according to claim 1 , wherein the crop comprises Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea Arabica, Coffea canephora, Coffea liberica, Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium, Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum, N. rustica, Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis, Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor ( S. vulgare ), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera , or Zea mays.
8. The method according to claim 6 , wherein the crop comprises Arachis hypogaea, Beta vulgaris spec. altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea Arabica, Coffea canephora, Coffea liberica, Cynodon dactylon, Glycine max, Gossypium hirsutum, Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium, Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum, N. rustica, Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor ( S. vulgare ), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera , or Zea mays.
9. The method according to claim 1 , wherein the herbicidal composition further comprises one or more: (i) further herbicides B, (ii) safeners C, (iii) liquid and/or solid carriers, (iv) surfactants, and/or (v) crop protection composition auxiliaries.
10. The method according to claim 1 , wherein the herbicidal composition further comprises a further herbicide B that is a PPO-inhibitor herbicide b4).
11. The method according to claim 10 , wherein the PPO-inhibitor herbicide b4) is selected from acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7), and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione.
12. The method according to claim 10 , wherein the PPO-inhibitor herbicide b4) is selected from acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon-ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen-ethyl, saflufenacil, sulfentrazone, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 45100-03-7), and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione.
13. The method according to claim 10 , wherein the PPO-inhibitor herbicide b4) is selected from flumioxazin, oxyfluorfen, saflufenacil, sulfentrazone, ethyl[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl) phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100), and 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinan-2,4-dione.
14. The method according to claim 10 , wherein the PPO-inhibitor herbicide is saflufenacil.
15. A method for controlling weeds in a crop area, comprising:
a) providing
(i) an herbicidal composition comprising an herbicidal benzoxazinone 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;
W is O or S; and
Z is O or S;
and
(ii) crop seed; and
(b) applying said herbicidal composition to the seed.
16. The method according to claim 15 , wherein said crop seed is herbicide-tolerant crop seed.
17. The method according to claim 15 , wherein the crop seed comprises seeds of corn, wheat, sunflower, cotton, rice, canola, oilseed rape, or soybean.
18. The method according to claim 15 , wherein the herbicidal composition further comprises one or more: (i) further herbicides B, (ii) safeners C, (iii) liquid and/or solid carriers, (iv) surfactants, and/or (v) crop protection composition auxiliaries.
19. The method according to claim 18 , wherein the herbicidal composition further comprises a further herbicide B that is a PPO-inhibitor herbicide b4).
20. The method according to claim 19 , wherein the PPO-inhibitor herbicide is saflufenacil.