SELECTIVE HERBICIDES BASED ON SUBSTITUTED ISOXAZOLIN CARBOXAMIDES AND ISOXADIFEN-ETHYL

Abstract

The invention relates to novel selective herbicidal active compound combinations which comprise substituted isoxazolincarboxamides or agrochemical acceptable salts thereof and isoxadifen-ethyl and which can be used with particularly good results for the selective control of weeds in various crops of useful plants.

Claims

1. A combination comprising (a) a substituted isoxazolincarboxamide of formula (I) or an agrochemical acceptable salt thereof ##STR00104## in which G represents OR.sup.4 or NR.sup.7R.sup.8 R.sup.1 and R.sup.2 each represent hydrogen; R.sup.3 represents (C.sub.1-C.sub.5)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.5)-alkenyl, (C.sub.2-C.sub.5)-alkinyl or (C.sub.1-C.sub.5)-alkoxy each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.5)-alkoxy and hydroxy; R.sup.4 represents hydrogen, or represents (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.5-C.sub.6)-cycloalkenyl, (C.sub.1-C.sub.4)-alkylphenyl or (C.sub.2-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, hydroxy, S(O).sub.n R.sup.5; R.sup.5 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, benzyl, CON((C.sub.1-C.sub.3)-alkyl).sub.2 or (C.sub.1-C.sub.8)-alkyl-C(O)—(C.sub.1-C.sub.8)-alkyl each optionally substituted “m” times by substituents from the group consisting of halogen and cyano; R.sup.6 represents hydrogen, or represents (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.8)-alkenyl or (C.sub.3-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.7, R.sup.8 independently of each other represent hydrogen, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, N((C.sub.1-C.sub.3)-alkyl).sub.2, S(O).sub.n R.sup.5, or R.sup.7 and R.sup.8 together with the nitrogen atom to which they are attached form a saturated or partially or fully unsaturated five-, six-, or seven-membered ring which may contain apart from the nitrogen atom “r” carbon atoms, “o” oxygen atoms and is optionally substituted “m” times by substituents from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halogen-(C.sub.1-C.sub.6)-alkyl, oxo, CO.sub.2R.sup.6; Z represents Z-1 to Z-8: ##STR00105## whereas the arrow represents the bonding to the group CO-G of the formula (I); X.sup.2, X.sup.4 and X.sup.6 independently of one another represent hydrogen or fluorine; X.sup.3 and X.sup.5 independently of one another represent hydrogen, chlorine, cyano or fluorine; or represents (C.sub.1-C.sub.3)-Alkyl, (C.sub.1-C.sub.3)-Alkoxy each optionally substituted “m” times by substituents from the group consisting of fluorine or chlorine; m represents 0, 1, 2, 3, 4 or 5; n represents 0, 1 or 2; o represents 0, 1 or 2; r represents 3, 4, 5 or 6; and (b) Isoxadifen-ethyl.

2. A combination according to claim 1, wherein the compound of formula (I) is (Ia) or an agrochemical acceptable salt thereof ##STR00106## in which X.sup.3, X.sup.5, R.sup.3 and G are as described above; Z means Z-1a, Z-1b, Z-2a, Z-3a, Z-4a, Z-5a, Z-6a, Z-7a, Z-8a, ##STR00107## wherein Z-4a means the mixture of both structures Z-4b and Z-4c; ##STR00108## and wherein Z-8a means the mixture of both structures Z-8b and Z-8c ##STR00109## and wherein the arrow means a bond to the group CO-G in formula (Ia).

3. A combination according to claim 1 wherein the application rate of the compound of formula (I) or salt is adapted to be between 0.1 and 1000 g per ha, optionally between 0.1 and 50 g per ha and wherein the application rate of the Isoxadifen-ethyl is adapted to be between 1 and 1000 g per ha, optionally between 10 and 200 g per ha.

4. A product comprising a combination according to claim 1 for controlling one or more undesirable plants.

5. A method for controlling one or more undesirable plants, comprising allowing a combination according to claim 1 to act on the undesirable plants and/or a habitat thereof.

6. A composition comprising in addition to a combination according to claim 1, one or more surfactants and/or extenders.

7. A process for preparing a herbicidal composition comprising mixing a combination according to any of claim 1 with one or more surfactants and/or extenders.

8. A method of reducing crop damage comprising treating seed of a crop with Isoxadifen-ethyl before sowing and applying a compound of formula (I) ##STR00110## in which G represents OR.sup.4 or NR.sup.7R.sup.8 R.sup.1 and R.sup.2 each represent hydrogen; R.sup.3 represents (C.sub.1-C.sub.5)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.5)-alkenyl, (C.sub.2-C.sub.5)-alkinyl or (C.sub.1-C.sub.5)-alkoxy each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.5)-alkoxy and hydroxy; R.sup.4 represents hydrogen, or represents (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.5-C.sub.6)-cycloalkenyl, (C.sub.1-C.sub.4)-alkylphenyl or (C.sub.2-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, hydroxy, S(O).sub.n R.sup.5; R.sup.5 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, benzyl, CON((C.sub.1-C.sub.3)-alkyl).sub.2 or (C.sub.1-C.sub.8)-alkyl-C(O)—(C.sub.1-C.sub.8)-alkyl each optionally substituted “m” times by substituents from the group consisting of halogen and cyano; R.sup.6 represents hydrogen, or represents (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.8)-alkenyl or (C.sub.3-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.7, R.sup.8 independently of each other represent hydrogen, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, N((C.sub.1-C.sub.3)-alkyl).sub.2, S(O).sub.n R.sup.5, or R.sup.7 and R.sup.8 together with the nitrogen atom to which they are attached form a saturated or partially or fully unsaturated five-, six-, or seven-membered ring which may contain apart from the nitrogen atom “r” carbon atoms, “o” oxygen atoms and is optionally substituted “m” times by substituents from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halogen-(C.sub.1-C.sub.6)-alkyl, oxo, CO.sub.2R.sup.6; Z represents Z-1 to Z-8: ##STR00111## whereas the arrow represents the bonding to the group CO-G of the formula (I); X.sup.2, X.sup.4 and X.sup.6 independently of one another represent hydrogen or fluorine; X.sup.3 and X.sup.5 independently of one another represent hydrogen, chlorine, cyano or fluorine; or represents (C.sub.1-C.sub.3)-Alkyl, (C.sub.1-C.sub.3)-Alkoxy each optionally substituted “m” times by substituents from the group consisting of fluorine or chlorine; m represents 0, 1, 2, 3, 4 or 5; n represents 0, 1 or 2; o represents 0, 1 or 2; r represents 3, 4, 5 or 6; or salt thereof or a combination/composition thereof in a post-emergence treatment.

9. A method of reducing crop damage comprising treating seed of a crop with Isoxadifen-ethyl before sowing and applying a compound of formula (I) ##STR00112## in which G represents OR.sup.4 or NR.sup.7R.sup.8 R.sup.1 and R.sup.2 each represent hydrogen; R.sup.3 represents (C.sub.1-C.sub.5)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.2-C.sub.5)-alkenyl, (C.sub.2-C.sub.5)-alkinyl or (C.sub.1-C.sub.5)-alkoxy each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.5)-alkoxy and hydroxy; R.sup.4 represents hydrogen, or represents (C.sub.1-C.sub.12)-alkyl, (C.sub.3-C.sub.7)-cycloalkyl, (C.sub.3-C.sub.7)-cycloalkyl-(C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.5-C.sub.6)-cycloalkenyl, (C.sub.1-C.sub.4)-alkylphenyl or (C.sub.2-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano, (C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)-alkoxycarbonyl, hydroxy, S(O).sub.n R.sup.5; R.sup.5 represents (C.sub.1-C.sub.8)-alkyl, (C.sub.2-C.sub.8)-alkenyl, (C.sub.3-C.sub.6)-cycloalkyl, benzyl, CON((C.sub.1-C.sub.3)-alkyl).sub.2 or (C.sub.1-C.sub.8)-alkyl-C(O)—(C.sub.1-C.sub.8)-alkyl each optionally substituted “m” times by substituents from the group consisting of halogen and cyano; R.sup.6 represents hydrogen, or represents (C.sub.1-C.sub.8)-alkyl, (C.sub.3-C.sub.6)-cycloalkyl, (C.sub.3-C.sub.8)-alkenyl or (C.sub.3-C.sub.8)-alkinyl each optionally substituted “m” times by substituents from the group consisting of halogen, cyano and (C.sub.1-C.sub.2)-alkoxy; R.sup.7, R.sup.8 independently of each other represent hydrogen, (C.sub.1-C.sub.6)-alkoxycarbonyl-(C.sub.1-C.sub.6)-alkyl, N((C.sub.1-C.sub.3)-alkyl).sub.2, S(O).sub.n R.sup.5, or R.sup.7 and R.sup.8 together with the nitrogen atom to which they are attached form a saturated or partially or fully unsaturated five-, six-, or seven-membered ring which may contain apart from the nitrogen atom “r” carbon atoms, “o” oxygen atoms and is optionally substituted “m” times by substituents from the group consisting of halogen, (C.sub.1-C.sub.6)-alkyl, halogen-(C.sub.1-C.sub.6)-alkyl, oxo, CO.sub.2R.sup.6; Z represents Z-1 to Z-8: ##STR00113## whereas the arrow represents the bonding to the group CO-G of the formula (I); X.sup.2, X.sup.4 and X.sup.6 independently of one another represent hydrogen or fluorine; X.sup.3 and X.sup.5 independently of one another represent hydrogen, chlorine, cyano or fluorine; or represents (C.sub.1-C.sub.3)-Alkyl, (C.sub.1-C.sub.3)-Alkoxy each optionally substituted “m” times by substituents from the group consisting of fluorine or chlorine; m represents 0, 1, 2, 3, 4 or 5; n represents 0, 1 or 2; o represents 0, 1 or 2; r represents 3, 4, 5 or 6; or salt thereof or combination/composition thereof in a pre-emergence treatment.

10. A method according to claim 5 wherein the crop is a genetically modified plant.

Description

USE EXAMPLES

[0094] Tank-Mix; Post-Emergence

A) Method Description

[0095] Seeds of crops (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were placed in sandy loam soil in peat pots, covered with soil and cultivated in a greenhouse under good growth conditions. Two to three weeks after sowing, the test plants were treated at the 1 to 3-leaf stage. The herbicide/safener active compound combinations according to the invention, formulated as wettable powders or emulsion concentrates, and, in parallel tests, the correspondingly formulated individual active compounds were sprayed onto the green parts of the plants in various dosages using an amount of water of 300 l/ha (converted).

[0096] The pots were returned under good growing conditions in a glasshouse and a visual assessment of herbicidal effects was made at intervals from 1 to 3 weeks after herbicide application (DAT=days after treatment). Assessment was on a percentage basis in comparison with untreated control plants (0%=no injury, 100%=complete kill).

[0097] The effectiveness of the safener treatment is displayed as:

Reduction[Difference]=herbicide damage without safener−herbicide damage with safener Reduction[%]=(Reduction[Difference]*100)/herbicide damage without safener

B) Tables with Data

a) Plant Species, Variety: ZEAMA Sileno, Safener (SAF): Isoxadifen-Ethyl

[0098]

TABLE-US-00002 TABLE 2 Herbicide HER SAF HER (HER) dose HER dose effect + [Example [g effect [g SAF Reduction Reduction No.] Assessment a.i./ha] [%] a.i./ha] [%] [Difference] [%] 1.68 Final 2 60 50 25 35 58 1.17 Final 8 95 50 20 75 79 1.17 Final 2 45 50 10 35 78 1.19 Final 8 40 50 20 20 50 1.29 Final 8 60 50 25 35 58 1.29 Final 32 75 100 25 50 67 1.27 Final 32 60 100 30 30 50 1.70 Final 2 88 50 35 53 60 1.69 Final 32 93 100 30 63 68 1.69 Final 8 92 50 33 59 64 1.59 Final 32 67 100 10 57 85 1.92 Final 32 97 100 38 59 61 1.92 Final 8 95 50 42 53 56 1.94 Final 32 94 100 32 62 66 1.94 Final 8 91 50 23 68 75 1.2 Final 32 96 100 75 21 22 1.2 Final 8 90 50 65 25 28 1.83 Final 32 85 100 20 65 76 1.83 Final 8 62 50 28 34 55 1.82 Final 32 96 100 75 21 22 1.82 Final 8 90 50 65 25 28 1.82 Final 32 92 100 55 37 40 1.82 Final 8 93 50 53 40 43 1.66 Final 32 97 100 47 50 52 1.66 Final 8 96 50 43 53 55 1.75 Final 32 88 100 43 45 51 1.75 Final 8 73 50 23 50 68 1.9 Final 32 85 100 22 63 74 1.9 Final 8 78 50 22 56 72 1.23 Final 32 70 100 30 40 57 1.23 Final 8 50 50 30 20 40 1.18 Final 32 97 100 20 77 79 1.18 Final 8 94 50 25 69 73 1.63 Final 32 88 100 43 45 51 1.63 Final 8 85 50 40 45 53 1.5 Final 32 96 100 47 49 51 1.5 Final 8 85 50 18 67 79

b) Plant Species, Variety: ZEAMA Abraxas, Safener (SAF): Isoxadifen-Ethyl

[0099]

TABLE-US-00003 TABLE 3 Herbicide HER SAF HER (HER) dose HER dose effect + [Example [g effect [g SAF Reduction Reduction No.] Assessment a.i./ha] [%] a.i./ha] [%] [Difference] [%] 1.1 Final 32 95 100 45 50 53 1.1 Final 8 93 50 20 73 78 1.76 Final 8 90 50 33 57 63 1.47 Final 32 62 100 38 24 39 1.58 Final 32 95 100 15 80 84 1.58 Final 8 62 50 17 45 73 1.22 Final 32 20 100 0 20 100 1.60 Final 32 94 100 57 37 39 1.60 Final 8 55 50 20 35 64 1.71 Final 32 91 100 35 56 62 1.71 Final 8 58 50 17 41 71 1.89 Final 32 45 100 17 28 62 1.89 Final 8 30 50 3 27 90 1.90 Final 2 25 100 5 20 80 1.86 Final 8 32 50 12 20 63

c) Plant Species, Variety: HORVS Montoya, Safener (SAF): Isoxadifen-Ethyl

[0100]

TABLE-US-00004 TABLE 4 Herbicide HER SAF HER (HER) dose HER dose effect + [Example Assessment [g effect [g SAF Reduction Reduction No.] [DAT] a.i./ha] [%] a.i./ha] [%] [Difference] [%] 1.68 10 DAT 0.25 20 50 0 20 100 1.26 10 DAT 2 70 50 50 20 29 1.26 10 DAT 0.5 40 50 10 30 75

5d) Plant Species, Variety: TRZAS Triso, Safener (SAF): Isoxadifen-Ethyl

[0101]

TABLE-US-00005 TABLE 5 Herbicide HER SAF HER (HER) dose HER dose effect + [Example Assessment [g effect [g SAF Reduction Reduction No.] [DAT] a.i./ha] [%] a.i./ha] [%] [Difference] [%] 1.68 21 DAT 1 93 50 70 23 25 1.68 21 DAT 0.25 40 50 20 20 50 1.26 21 DAT 0.5 40 50 10 30 75

[0102] Seed Treatment; Pre-Emergence

[0103] A) Method Description

[0104] For the safener seed treatment, sufficient seeds of the respective crops (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were weighed into screw top glass bottles approximately twice the volume of the seeds.

[0105] The specified safeners, formulated as wettable powder (WP) were weighed out so that the specified rates (g a.i./kg seed) would be obtained, dissolved in water (1 ml water per 10 g of seeds), and added to the seeds to produce a slurry.

[0106] The bottles were capped and then placed in an overhead shaker (set at medium speed for ca. 60 minutes) so that the seeds were evenly coated with the slurry. The bottles were uncapped and the seeds were either placed on paper and dried for an interval of 3-4 hours prior to sowing, or directly sown. Seeds were placed in sandy loam soil in pots of a diameter of 7-8 cm, and covered with soil.

[0107] Pre-emergence application of the specified herbicides was done subsequently, on two sets of plants:

[0108] a) seed treatment with safener, as described above

[0109] b) no safener treatment

[0110] The herbicides were formulated as WP and was sprayed onto the soil surface as an aqueous suspension at an equivalent water application rate of 300 l/ha.

[0111] After application, the test plants were kept in the greenhouse under good growth conditions. At intervals up to 4 weeks after application (=28 days after treatment; DAT), % crop damage observed on the treated plants was scored visually in comparison to control plants that had not received any safener or herbicide treatment.

[0112] Values in the table below are mean values of at least 2 replicates.

[0113] The effectiveness of the safener treatment is displayed as:

Reduction[Difference]=herbicide damage without safener−herbicide damage with safener Reduction[%]=(Reduction[Difference]*100)/herbicide damage without safener

[0114] B) Tables with Data

[0115] a) Plant Species, Variety: TRZAS Triso, Safener (SAF): Isoxadifen-Ethyl

TABLE-US-00006 TABLE 6 SAF Herbicide HER dose HER (HER) dose HER [g effect + [Example Assessment [g effect a.i./kg SAF Reduction Reduction No.] [DAT] a.i./ha] [%] seed] [%] [Difference] [%] 1.68 11 (Interim) 5 45 0.25 25 20 44 1.68 21 (Final) 5 45 0.25 20 25 56 1.93 11 (Interim) 15 50 0.25 5 45 90 1.93 21 (Final) 15 65 0.25 5 60 92 1.93 21 (Final) 5 35 0.25 0 35 100 1.91 21 (Final) 15 40 0.25 10 30 75 1.26 11 (Interim) 15 65 0.25 45 20 31 1.26 21 (Final) 15 75 0.25 15 60 80 1.18 11 (Interim) 15 45 0.25 15 30 67 1.5 11 (Interim) 15 25 0.25 5 20 80 1.36 11 (Interim) 15 70 0.25 50 20 29 1.36 21 (Final) 15 70 0.25 25 45 64 1.7 11 (Interim) 15 45 0.25 20 25 56

[0116] b) Plant Species, Variety: HORVS Montoya, Safener (SAF): Isoxadifen-Ethyl

TABLE-US-00007 TABLE 7 SAF Herbicide HER dose HER (HER) dose HER [g effect + [Example Assessment [g effect a.i./kg SAF Reduction Reduction No.] [DAT] a.i./ha] [%] seed] [%] [Difference] [%] 1.68 11 (Interim) 15 65 0.25 45 20 31 1.26 21 (Final) 15 50 0.25 5 45 90 1.18 11 (Interim) 15 40 0.25 20 20 50 1.18 21 (Final) 15 40 0.25 5 35 88 1.36 21 (Final) 15 70 0.25 40 30 43 1.36 21 (Final) 5 45 0.25 25 20 44 1.7 11 (Interim) 15 50 0.25 25 25 50 1.7 21 (Final) 15 30 0.25 5 25 83

[0117] c) Plant Species, Variety: ZEAMA Sileno, Safener (SAF): Isoxadifen-Ethyl

TABLE-US-00008 TABLE 8 SAF Herbicide HER dose HER (HER) dose HER [g effect + [Example Assessment [g effect a.i./kg SAF Reduction Reduction No.] [DAT] a.i./ha] [%] seed] [%] [Difference] [%] 1.68 14 40 93 0.25 70 23 25 1.70 14 80 95 0.25 70 25 26 1.70 26 80 95 0.25 75 20 21 1.70 14 40 80 0.25 45 35 44 1.70 26 40 85 0.25 40 45 53 1.69 14 40 95 0.25 55 40 42 1.69 26 40 90 0.25 65 25 28 1.92 14 40 75 0.25 5 70 93 1.92 26 40 70 0.25 10 60 86 1.26 14 80 70 0.25 45 25 36 1.26 26 80 70 0.25 15 55 79 1.26 26 40 50 0.25 5 45 90 1.2 14 80 45 0.25 10 35 78 1.9 14 80 30 0.25 5 25 83 1.18 14 40 40 0.25 15 25 63 1.63 14 40 60 0.25 30 30 50 1.63 26 40 25 0.25 0 25 100 1.5 14 80 60 0.25 30 30 50 1.5 26 80 45 0.25 20 25 56 1.29 14 80 60 0.25 40 20 33