SELECTIVE HERBICIDES BASED ON SUBSTITUTED ISOXAZOLIN CARBOXAMIDES AND MEFENPYR-DIETHYL

Abstract

The invention relates to novel selective herbicidal active compound combinations which comprise substituted isoxazolincarboxamides or agrochemical acceptable salts thereof and mefenpyr-diethyl 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 ##STR00103## 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.nR.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.nR.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: ##STR00104## v 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) mefenpyr-diethyl.

2. A combination according to claim 1, wherein the compound of formula (I) is (Ia) or an agrochemical acceptable salt thereof ##STR00105## 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, ##STR00106## wherein Z-4a means the mixture of both structures Z-4b and Z-4c; ##STR00107## and wherein Z-8a means the mixture of both structures Z-8b and Z-8c ##STR00108## 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 200 g per ha and wherein the application rate of the mefenpyr-diethyl 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 mefenpyr-diethyl before sowing and applying a compound of formula (I) ##STR00109## 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.nR.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.nR.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: ##STR00110## v 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 post-emergence treatment (step 2).

9. A method of reducing crop damage comprising treating seed of a crop with mefenpyr-diethyl before sowing and applying a compound of formula (I) ##STR00111## 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.nR.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.nR.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: ##STR00112## v 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 combinations/compositions thereof in a pre-emergence treatment.

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

Description

USE EXAMPLES

[0100] Tank-Mix; Post-Emergence

[0101] A) Method Description

[0102] 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).

[0103] 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).

[0104] 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

[0105] B) Tables with Data

[0106] a) Plant Species, Variety: HORVS Montoya, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00002 TABLE 2 HER Herbicide HER HER SAF effect + (HER) Assessment dose effect dose SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] [g a.i./ha] [%] [Difference] [%] 1.68 21 DAT 2 40 100 10 30 75 1.68 21 DAT 0.5 30 50 0 30 100 1.26 21 DAT 2 60 100 0 60 100 1.72 10 DAT 32 50 100 10 40 80 1.72 10 DAT 8 30 50 0 30 100 1.93 10 DAT 32 90 100 30 60 67 1.93 10 DAT 8 85 50 10 75 88 1.67 10 DAT 16 60 100 0 60 100 1.67 10 DAT 4 30 50 0 30 100 1.78 21 DAT 32 40 100 10 30 75 1.79 10 DAT 24 70 100 0 70 100 1.79 10 DAT 6 20 50 0 20 100 1.61 10 DAT 8 50 50 30 20 40 1.88 21 DAT 1.5 40 50 10 30 75 1.47 21 DAT 48 85 100 60 25 29 1.94 10 DAT 32 90 100 70 20 22 1.94 10 DAT 8 90 50 30 60 67 1.94 10 DAT 2 30 50 0 30 100 1.12 10 DAT 48 60 100 0 60 100 1.60 21 DAT 8 80 100 20 60 75 1.71 21 DAT 32 70 100 50 20 29 1.71 21 DAT 8 50 50 20 30 60 1.2 10 DAT 8 30 100 0 30 100 1.2 10 DAT 2 20 50 0 20 100 1.20 21 DAT 32 80 100 40 40 50 1.20 21 DAT 8 30 50 0 30 100 1.65 10 DAT 8 80 50 20 60 75 1.85 10 DAT 32 80 100 20 60 75 1.85 10 DAT 8 20 50 0 20 100 1.18 10 DAT 32 80 100 10 70 88 1.18 10 DAT 8 20 50 0 20 100 1.5 21 DAT 2 20 50 0 20 100 1.36 10 DAT 1 80 50 60 20 25 1.91 21 DAT 24 30 100 10 20 67

[0107] b) Plant Species, Variety: TRZAS Triso, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00003 TABLE 3 HER Herbicide HER HER SAF effect + (HER) Assessment dose effect dose SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] [g a.i./ha] [%] [Difference] [%] 1.68 21 DAT 4 85 100 60 25 29 1.68 21 DAT 1 80 50 30 50 63 1.26 21 DAT 2 90 50 50 40 44 1.72 21 DAT 32 60 100 10 50 83 1.93 21 DAT 8 93 50 50 43 46 1.93 21 DAT 2 85 50 10 75 88 1.67 10 DAT 16 70 100 20 50 71 1.67 10 DAT 4 50 50 10 40 80 1.78 10 DAT 24 70 100 30 40 57 1.78 10 DAT 6 70 50 10 60 86 1.78 10 DAT 1.5 20 50 0 20 100 1.79 10 DAT 24 50 100 10 40 80 1.79 10 DAT 6 30 50 0 30 100 1.61 10 DAT 24 50 100 20 30 60 1.61 10 DAT 6 50 50 10 40 80 1.88 21 DAT 2 70 50 30 40 57 1.47 21 DAT 16 80 100 20 60 75 1.47 21 DAT 4 30 50 10 20 67 1.58 21 DAT 8 93 50 40 53 57 1.58 21 DAT 2 85 50 10 75 88 1.94 21 DAT 24 85 100 10 75 88 1.94 21 DAT 6 85 50 0 85 100 1.94 21 DAT 1.5 20 50 0 20 100 1.7 10 DAT 8 93 50 70 23 25 1.7 10 DAT 2 50 50 0 50 100 1.71 10 DAT 32 85 100 20 65 76 1.71 10 DAT 8 50 50 0 50 100 1.2 10 DAT 8 90 50 50 40 44 1.20 10 DAT 32 50 100 30 20 40 1.20 10 DAT 8 20 50 0 20 100 1.65 10 DAT 8 20 50 0 20 100 1.5 10 DAT 2 50 50 0 50 100 1.36 21 DAT 1 85 50 20 65 76 1.91 21 DAT 24 80 100 50 30 38 1.91 21 DAT 6 90 50 20 70 78 1.91 21 DAT 1.5 70 50 0 70 100

[0108] Treatment 1 Day Before

[0109] A) Method Description

[0110] Seeds of crops (spring wheat, TRZAS; spring barley, HORVS; maize, ZEAMA) were placed in sandy loam soil in pots of a diameter of 7-8 cm, covered with soil, and cultivated in a greenhouse under good growth conditions until plants were at the 1-3 leaf stage (BBCH 11-13). For split safener and herbicide treatment, first the safener was applied followed by the herbicide treatment on the following day. The safener and herbicides were formulated as WP and sprayed onto the green parts of the plants as an aqueous suspension at an equivalent water application rate of 300 l/ha, with addition of wetting agent and adjuvants (e.g. Mero, 1.5 l/ha; ammonium sulphate, 2 kg/ha). An equivalent set of plants was treated with the herbicides but without the prior safener treatment.

[0111] After application, the test plants were kept in the greenhouse under good growth conditions. 10 and 21 days after treatment (DAT) with the herbicide, % 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] 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

[0113] B) Tables with Data

[0114] a) Plant Species, Variety: HORVS Montoya, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00004 TABLE 4 HER Herbicide HER HER SAF effect + (HER) Assessment dose effect dose SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] [g a.i./ha] [%] [Difference] [%] 1.46 21 DAT 50 65 50 20 45 69 1.46 21 DAT 25 45 50 10 35 78 1.47 21 DAT 25 60 50 40 20 33 1.12 21 DAT 100 70 50 50 20 29 1.12 10 DAT 50 55 50 20 35 64 1.9 10 DAT 100 40 100 20 20 50

[0115] b) Plant Species, Variety: TRZAS Triso, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00005 TABLE 5 HER Herbicide HER HER SAF effect + (HER) Assessment dose effect dose SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] [g a.i./ha] [%] [Difference] [%] 1.46 21 DAT 200 80 50 5 75 94 1.46 21 DAT 100 60 50 5 55 92 1.47 21 DAT 50 80 50 60 20 25 1.47 21 DAT 25 75 50 35 40 53 1.12 21 DAT 200 40 50 20 20 50 1.9 21 DAT 200 70 100 25 45 64 1.9 21 DAT 100 60 100 20 40 67

[0116] Seed Treatment; Pre-Emergence

[0117] A) Method Description

[0118] 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.

[0119] 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.

[0120] 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.

[0121] Pre-emergence application of the specified herbicides was done subsequently, on two sets of plants:

[0122] a) seed treatment with safener, as described above

[0123] b) no safener treatment

[0124] 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.

[0125] 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.

[0126] Values in the table below are mean values of at least 2 replicates. 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

[0127] B) Tables with Data

[0128] a) Plant Species, Variety: TRZAS Triso, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00006 TABLE 6 SAF HER Herbicide HER HER dose effect + (HER) Assessment dose effect [g a.i./kg SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] seed] [%] [Difference] [%] 1.68 11 (Interim) 15 80 0.25 30 50 63 1.68 21 (Final) .sup.  15 85 0.25 30 55 65 1.68 11 (Interim) 5 45 0.25 15 30 67 1.68 21 (Final) .sup.  5 45 0.25 5 40 89

[0129] b) Plant Species, Variety: HORVS Montoya, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00007 TABLE 7 SAF HER Herbicide HER HER dose effect + (HER) Assessment dose effect [g a.i./kg SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] seed] [%] [Difference] [%] 1.68 11 (Interim) 15 65 0.25 0 65 100 1.68 21 (Final) .sup.  15 80 0.25 60 20 25 1.68 11 (Interim) 5 25 0.25 5 20 80 1.68 21 (Final) .sup.  5 30 0.25 5 25 83

[0130] Seed Treatment; Post-Emergence

[0131] A) Method Description

[0132] For safener seed treatment trials, sufficient seed amounts of the respective crops (spring wheat (TRZAS); spring barley (HORVS)) were weighed into screw cap glass bottles with a minimum volume trice of the seeds.

[0133] As a first step, specified safeners formulated as wettable powder (WP) or wettable granules (WG) were weighed out for the required dosages (g a.i./kg seed), corresponding to the seed amounts. The safener amounts were mixed with a coloured slurry blind formulation type, prediluted with milk at 3.5% fat rate (25 mgs slurry formulation plus 2 ml milk per 10 grams of seed). A tube roller was used for coating. The solutions were gradually pipetted each on the rotating seeds followed by coating for min. 3 hours until all liquid had been soaked up by the seeds. Thereafter, the coated seeds were put flat on open trays for drying over night at room temperature.

[0134] Treated seeds were then placed into pots (7 cm diameter) on the surface of sandy loam, pressed down, flat covered with additional soil and finally covered with sandy soil, also pressed down, watered, and kept under good growth conditions in a greenhouse, until the plants had reached 2-leaf-stage (BBCH 12).

[0135] At that stage, post-emergence application of the specified herbicides was done on:

[0136] a) pot sets containing plants with safener-coated seeds as described above,

[0137] b) as a reference, pot sets of plants without seed treatment.

[0138] The herbicides were formulated as wettable powder (WP). Equivalent to the spray area, compound amounts were weighed out and diluted related to the water application rate (300 l/ha) to an aqueous suspension plus additive (1 l/ha MERO). Dosage related equivalents were conventionally sprayed on trays with the potted plants.

[0139] After application, the test plants were kept under good growth conditions in a greenhouse.

[0140] Assessment timings were 10 and 21 days after treatment (DAT) with the herbicide, by visual scoring of the crop damage in % (comparison of untreated with treated plants, either sprayed only with herbicide or with herbicide on plants with treated seeds).

[0141] 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

[0142] B) Tables with Data

[0143] a) Plant Species, Variety: HORVS Montoya, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00008 TABLE 8 SAF HER Herbicide HER HER dose effect + (HER) Assessment dose effect [g a.i./kg SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] seed] [%] [Difference] [%] 1.68 21 DAT 2 40 0.5 0 40 100 1.68 21 DAT 0.5 30 0.5 0 30 100 1.72 10 DAT 32 50 0.5 0 50 100 1.72 10 DAT 8 30 0.5 0 30 100 1.93 10 DAT 32 90 0.5 70 20 22 1.93 10 DAT 8 85 0.5 30 55 65 1.78 21 DAT 32 40 0.5 10 30 75 1.78 21 DAT 8 20 0.5 0 20 100 1.79 10 DAT 24 70 0.5 40 30 43 1.61 10 DAT 32 60 0.5 20 40 67 1.61 10 DAT 8 50 0.5 10 40 80 1.88 21 DAT 8 85 0.5 20 65 76 1.88 21 DAT 2 50 0.5 10 40 80 1.88 21 DAT 0.5 20 0.5 0 20 100 1.47 21 DAT 48 85 0.5 20 65 76 1.58 21 DAT 32 95 0.5 40 55 58 1.58 21 DAT 8 95 0.5 0 95 100 1.94 10 DAT 32 90 0.5 30 60 67 1.94 10 DAT 8 90 0.5 20 70 78 1.94 10 DAT 2 30 0.5 0 30 100 1.12 21 DAT 48 50 0.5 20 30 60 1.12 21 DAT 12 20 0.5 0 20 100 1.60 21 DAT 8 80 0.5 10 70 88 1.7 21 DAT 32 95 0.5 50 45 47 1.7 21 DAT 2 70 0.5 40 30 43 1.71 21 DAT 32 70 0.5 40 30 43 1.71 21 DAT 8 50 0.5 30 20 40 1.20 21 DAT 32 80 0.5 20 60 75 1.20 21 DAT 8 30 0.5 10 20 67 1.65 10 DAT 32 80 0.5 50 30 38 1.65 10 DAT 8 80 0.5 20 60 75 1.85 10 DAT 32 80 0.5 30 50 63 1.23 21 DAT 32 30 0.5 10 20 67 1.23 21 DAT 8 20 0.5 0 20 100 1.18 10 DAT 32 80 0.5 20 60 75 1.5 21 DAT 32 80 0.5 60 20 25 1.5 21 DAT 2 20 0.5 0 20 100 1.36 21 DAT 16 95 0.5 70 25 26 1.36 21 DAT 4 93 0.5 50 43 46 1.91 21 DAT 24 30 0.5 10 20 67

[0144] b) Plant Species, Variety: TRZAS Triso, Safener (SAF): Mefenpyr-diethyl

TABLE-US-00009 TABLE 9 SAF HER Herbicide HER HER dose effect + (HER) Assessment dose effect [g a.i./kg SAF Reduction Reduction [Example No.] [DAT] [g a.i./ha] [%] seed] [%] [Difference] [%] 1.68 21 DAT 4 85 0.5 30 55 65 1.68 21 DAT 1 80 0.5 20 60 75 1.26 21 DAT 8 93 0.5 70 23 25 1.26 21 DAT 2 90 0.5 30 60 67 1.72 21 DAT 32 60 0.5 10 50 83 1.72 21 DAT 8 20 0.5 0 20 100 1.93 21 DAT 32 95 0.5 20 75 79 1.93 21 DAT 8 93 0.5 10 83 89 1.93 21 DAT 2 85 0.5 0 85 100 1.67 10 DAT 16 70 0.5 20 50 71 1.67 10 DAT 4 50 0.5 10 40 80 1.78 10 DAT 24 70 0.5 30 40 57 1.78 10 DAT 6 70 0.5 30 40 57 1.79 10 DAT 24 50 0.5 30 20 40 1.61 10 DAT 8 50 0.5 10 40 80 1.88 21 DAT 8 85 0.5 20 65 76 1.88 21 DAT 2 70 0.5 10 60 86 1.47 21 DAT 16 80 0.5 10 70 88 1.47 21 DAT 4 30 0.5 0 30 100 1.58 21 DAT 32 93 0.5 10 83 89 1.58 21 DAT 8 93 0.5 0 93 100 1.58 21 DAT 2 85 0.5 0 85 100 1.94 21 DAT 24 85 0.5 20 65 76 1.94 21 DAT 6 85 0.5 10 75 88 1.94 21 DAT 1.5 20 0.5 0 20 100 1.60 21 DAT 32 95 0.5 10 85 89 1.60 21 DAT 8 93 0.5 0 93 100 1.7 10 DAT 8 93 0.5 40 53 57 1.7 10 DAT 2 50 0.5 0 50 100 1.71 10 DAT 32 85 0.5 0 85 100 1.71 10 DAT 8 50 0.5 0 50 100 1.2 10 DAT 32 90 0.5 30 60 67 1.2 10 DAT 8 90 0.5 10 80 89 1.20 10 DAT 32 50 0.5 0 50 100 1.20 10 DAT 8 20 0.5 0 20 100 1.65 10 DAT 8 20 0.5 0 20 100 1.23 21 DAT 8 20 0.5 0 20 100 1.5 21 DAT 32 95 0.5 30 65 68 1.5 21 DAT 8 90 0.5 10 80 89 1.36 21 DAT 1 85 0.5 0 85 100 1.36 21 DAT 16 95 0.5 50 45 47 1.36 21 DAT 4 93 0.5 30 63 68 1.91 21 DAT 24 80 0.5 10 70 88 1.91 21 DAT 6 90 0.5 20 70 78 1.91 21 DAT 1.5 70 0.5 10 60 86