PELARGONIC ACID-BASED HERBICIDE COMPOSITIONS

Abstract

The present invention relates to a concentrated emulsifiable composition comprising pelargonic acid and at least one emulsifying agent belonging to the class of anionic surfactants, preferably in acid form, at least one emulsifying agent belonging to the class of non-ionic surfactants and at least an organic solvent, a process for preparing said composition and use of said composition in herbicidal applications and as desiccant harvest aid. Said composition advantageously also finds use as a plant growth regulator.

Claims

1. A composition comprising: (a) 40-90% by weight of pelargonic acid; and (b) at least one emulsifying agent belonging to the class of anionic surfactants having formula (I) up to 15% by weight
(R—(OCHR.sub.1—CHR.sub.2).sub.n—(OCHR.sub.3—CHR.sub.4).sub.m—O—).sub.q—Z where R is a linear or branched C.sub.4-C.sub.18 alkyl radical, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H or CH.sub.3, n and m are identical or different integers from 0 to 30 and at least one of them is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) 5-55% by weight of at least one organic solvent, (d) from 1 to <15% by weight of at least one emulsifying agent belonging to the class of non-ionic surfactants; wherein the ratio between the weight content of the sum of anionic surfactants (b) and non-ionic surfactants (d) respect to pelargonic acid is 0.05-0.15.

2. The composition according to claim 1 comprising, with respect to the total weight of the composition: (a) 40-85% by weight of pelargonic acid, (b) 5-10% by weight of at least one emulsifying agent belonging to the class of anionic surfactants having formula (I)
(R—(OCHR.sub.1—CHR.sub.2).sub.n—(OCHR.sub.3—CHR.sub.4).sub.m—O—).sub.q—Z where R is a linear or branched C.sub.4-C.sub.18 alkyl radical, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H or CH.sub.3, n and m are identical or different integers from 0 to 30 and at least one of them is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) 5-55% by weight of at least one organic solvent, (d) 1-10% by weight of at least one emulsifying agent belonging to the class of non-ionic surfactants; wherein the ratio between the weight content of the sum of anionic surfactants (b) and non-ionic surfactants (d) respect to pelargonic acid is 0.05-0.15.

3. The composition according to claim 1, in which the content of the anionic surfactants (b) is above 5% by weight, with respect to the total weight of anionic and non-ionic surfactants.

4. The composition according to claim 1, wherein the emulsifying agent (b) belongs to the class of anionic surfactants in acid form.

5. The composition according to claim 1, wherein the anionic surfactant is selected from the group consisting of mono- and di-esterified phosphoric acids.

6. The composition according to claim 1, wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are H.

7. The composition according to claim 1, wherein only one of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is CH.sub.3.

8. The composition according to claim 1, wherein the emulsifying agent (b) is selected from: mono-[alkyl-polyethylene glycol] phosphate, mono-[alkyl-polyethylene glycol] phosphate, mono-[alkyl-polyethylene glycol] sulfate.

9. The composition according to claim 1, wherein the organic solvent is selected from the group consisting of aliphatic hydrocarbons, esters of carboxylic acids such as, for example, diesters of dicarboxylic acids or ester amides of dicarboxylic acids, alcohols, unmodified vegetable oils (triglycerides) and transesterified vegetable oils with C.sub.1-C.sub.4 lower alcohols.

10. A process for producing the composition according to claim 1, comprising mixing: (a) pelargonic acid and (b) at least one emulsifying agent belonging to the class of anionic surfactants having formula (I)
(R—(OCHR.sub.1—CHR.sub.2).sub.n—(OCHR.sub.3—CHR.sub.4).sub.m—O—).sub.q—Z where R is a linear or branched C.sub.4-C.sub.18 alkyl radical, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently H or CH.sub.3, n and m are identical or different integers from 0 to 30 and at least one of them is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) at least one organic solvent, (d) at least one emulsifying agent belonging to the class of non-ionic surfactants.

11. An aqueous emulsion comprising: the composition according to claim 1, and an aqueous phase.

12. An aqueous emulsion comprising: 0.1-15% by volume, relative to the total volume of the aqueous emulsion, of the composition according to claim 1, and 85-99.9% by volume, relative to the total volume of the aqueous emulsion, of an aqueous phase.

13. A method for protecting a plant from harmful organisms which comprising applying to the plant the aqueous emulsion according to claim 11 as an herbicide.

14. A method for controlling the growth of a plant or parts thereof, which comprises applying the aqueous emulsion according to claim 11 as a plant growth regulator.

15. A method for controlling or suppressing the growth of a plant, said method comprising applying the aqueous emulsion according to claim 11 to the plant.

16. The composition according to claim 2, in which the content of the anionic surfactants (b) is above 5% by weight, with respect to the total weight of anionic and non-ionic surfactants.

17. The composition according to claim 2, wherein the emulsifying agent (b) belongs to the class of anionic surfactants in acid form.

18. The composition according to claim 3, wherein the emulsifying agent (b) belongs to the class of anionic surfactants in acid form.

19. The composition according to claim 2, wherein the anionic surfactant is selected from the group consisting of mono- and di-esterified phosphoric acids.

20. The composition according to claim 3, wherein the anionic surfactant is selected from the group consisting of mono- and di-esterified phosphoric acids.

Description

EXAMPLES

[0151] Materials [0152] Pelargonic acid (98% purity by weight), obtained by the oxidative cleavage of high oleic sunflower oil. [0153] Commercially available herbicide formulation under the trade name BELOUKHA® containing pelargonic acid (72% by weight corresponding to approximately 680 g/l of active ingredient and without anionic and cationic surfactant) (Label authorised by Executive Decree of 26 Feb. 2016). [0154] Emulsifier A (anionic surfactant): [cetyl-polyethylene glycol (10 EO)-polypropylene glycol (5 PO)] phosphate acid, [0155] Emulsifier B (anionic surfactant): [cetyl stearyl polyethylene glycol (11 EO)] phosphate acid, [0156] Emulsifier C (anionic surfactant): [dodecyl tetradecyl polyethylene glycol (2EO)] sodium sulfate, [0157] Emulsifier D (non-ionic surfactant): Sorbitan Mono Oleate polyethoxylate (20 EO), [0158] Emulsifiers E (non-ionic surfactant): Sorbitan Mono Oleate, [0159] Emulsifier F (non-ionic surfactant): PEG-80 sorbitan laurate, [0160] Organic solvent A: methyl esters of fatty acids mainly comprising Methyl Oleate.

Example 1

[0161] A composition was prepared by mixing, with respect to the total weight of the composition: [0162] 80.7% by weight of pelargonic acid [0163] 6% by weight of Emulsifier A [0164] 3% by weight of Emulsifier D [0165] 1% by weight of Emulsifier E [0166] 9.3% by weight of Solvent A.

Example 2

[0167] A composition was prepared by mixing, with respect to the total weight of the composition: [0168] 80.7% by weight of pelargonic acid [0169] 6% by weight of Emulsifier B [0170] 3% by weight of Emulsifier D [0171] 1% by weight of Emulsifier E [0172] 9.3% by weight of Solvent A.

Example 3

[0173] A composition was prepared by mixing, with respect to the total weight of the composition: [0174] 80.7% by weight of pelargonic acid [0175] 6% by weight of Emulsifier C [0176] 3% by weight of Emulsifier D [0177] 1% by weight of Emulsifier E [0178] 9.3% by weight of Solvent A.

Comparative Example 4

[0179] Commercially available herbicide formulation under the trade name BELOUKHA® containing pelargonic acid (72% by weight corresponding to approximately 680 g/l active ingredient).

Comparative Example 5

[0180] A composition was prepared by mixing, with respect to the total weight of the composition: [0181] 80% by weight of pelargonic acid [0182] 5% by weight of Emulsifier D [0183] 5% by weight of Emulsifier F [0184] 10% by weight of Solvent A.

Example 6

[0185] A composition was prepared by mixing, with respect to the total weight of the composition: [0186] 80% by weight of pelargonic acid [0187] 1% by weight of Emulsifier A [0188] 4% by weight of Emulsifier D [0189] 5% by weight of Emulsifier F [0190] 10% by weight of Solvent A.

Comparative Example 7

[0191] A composition was prepared by mixing, with respect to the total weight of the composition: [0192] 41% by weight of pelargonic acid [0193] 1% by weight of Emulsifier A [0194] 9% by weight of Emulsifier D [0195] 49% by weight of Solvent A.

[0196] In the composition of Comparative Example 7, the ratio between the weight content of the sum of anionic surfactants (b) and non-ionic surfactants (d) respect to pelargonic acid is 0.25, so higher than 0.15.

[0197] The compositions of Examples 1-3 have a density of 0.91 g/cm.sup.3 at ambient temperature, Example 6 and Comparative Example 5 have a density of 0.92 g/cm.sup.3 at ambient temperature. Examples 1-3, 6 and Comparative Example 5 have an active ingredient concentration (i.e. 100% pelargonic acid) of approximately 720 g/1.

[0198] The compositions of Comparative Example 7 have a density of 0.90 g/cm.sup.3 at ambient temperature and an active ingredient concentration (i.e. 100% pelargonic acid) of approximately 360 g/1.

[0199] The compositions of Examples 1-3, 6 and Comparative Examples 4, 5 and 7 were diluted in water at different concentrations and tested for: [0200] emulsion stability (Example 8, Tables 2-4), evaluated for emulsions prepared by diluting the compositions of Examples 1-3 and Comparative Example 4 at 8 and 10% v/v; [0201] herbicidal activity (Example 9, Tables 5-6) by distributing the prepared diluted emulsions in the field: [0202] the composition of Example 1 at 6.0 and 7.55% v/v (doses of 8640 g/ha and 10880 g/ha of active ingredient), [0203] the composition of Examples 2, 3, 6 and of Comparative Example 5 at 7.55% v/v (doses of 10880 g/ha of active ingredient), [0204] the composition in Comparative Example 4 at 8% v/v (dose equal to 10880 g/ha of active ingredient), [0205] the composition in Comparative Example 7 at 15.10% v/v (dose equal to 10880 g/ha of active ingredient); [0206] effectiveness in controlling tobacco buds (Example 10, Table 7) by applying the prepared emulsions by diluting: [0207] the composition in Example 1 at 0.6 and 1% v/v (doses of 2592 g/ha and 4320 g/ha active ingredient), [0208] the composition of Comparative Example 4 at 1.2% v/v (dose equal to 4896 g/ha of active ingredient); [0209] effectiveness in the control of suckers in grape vines (Example 11, Table 8) by applying the prepared emulsions by diluting: [0210] the composition in Example 1 at 7.55% v/v (doses of 10880 g/ha active ingredient), [0211] the composition of Comparative Example 4 at 8% v/v (dose equal to 10880 g/ha of active ingredient); [0212] effectiveness in the weed control in apple orchard (Example 12, Table 9) by applying the prepared emulsions by diluting: [0213] the composition in Example 1 at 6.00 and 7.55% v/v (doses of 8640 and of 10880 g/ha active ingredient), [0214] the composition of Comparative Example 4 at 8% v/v (dose equal to 10880 g/ha of active ingredient); [0215] effectiveness as pre-harvest desiccant in potato (Example 13, Table 10) by applying the prepared emulsions by diluting: [0216] the composition in Example 1 at 6.00 and 7.55% v/v (doses of 8640 and 10880 g/ha active ingredient), [0217] the composition of Comparative Example 4 at 8% v/v (dose equal to 10880 g/ha of active ingredient).

Example 8. Emulsion Stability Comparison

[0218] The stability of the aqueous emulsions prepared from the compositions in Examples 1-3 and Comparative Example 4 was tested at different temperatures and using water of different hardness, according to standard CIPAC method MT 36 (paragraph 36.1.1—hand shaking), under the conditions indicated below. The stability of 8 and 10% v/v emulsions was tested at 6, 20 and 30° C. in standard waters A and D (characteristics given in Table 1) and was assessed after 2 h, 24 h and, finally, after redispersion, at 24 h+30 min, verifying in all the tested conditions, a better behaviour in comparison with the commercial product.

TABLE-US-00001 TABLE 1 Table 1. Characteristics of the standard waters used. Hardness French degrees Water Ca:Mg ratio (ppm CaCO.sub.3) ° F. pH Standard A 1:1 20 2 5-6 Standard D 4:1 342 34.2 6-7

TABLE-US-00002 TABLE 2 Table 2. ml of oil separated at 2 h, 24 h and 24 h + 30 min from 8% v/v emulsions in standard water D, at 20° C. Emulsions at 8% v/v 20° C. in standard water D 2 hours 24 hours 24 hours + 30 min Example 1 0 <0.5 0 Example 2 0 1 0 Example 3 0 1 0 Comparative example 4 1 4 0.5

TABLE-US-00003 TABLE 3 Table 3. ml of oil separated at 2 h, 24 h and 24 h + 30 min from 10% v/v emulsions in standard water A, at 6° and at 30° C. Emulsions at 10% v/v 6° C. 30° C. in standard water A 2 hours 24 hours 24 hours + 30 min 2 hours 24 hours 24 hours + 30 min Example 1 0 0 0 0 <2 0 Comparative example 4 0.5 4 0.5 1 4 1

TABLE-US-00004 TABLE 4 Table 4. ml of oil separated at 2 h, 24 h and 24 h + 30 min from 10% v/v emulsions in standard water D, at 6° and at 30° C. Emulsions at 10% v/v 6° C. 30° C. in standard water D 2 hours 24 hours 24 hours + 30 min 2 hours 24 hours 24 hours + 30 min Example 1 0 0.5 0 0 <2 0 Comparative example 4 1 3 0.5 1 4 1

[0219] As shown by the results in Table 2-4, the aqueous emulsions according to the present invention are more stable than those prepared from equal dilutions of the herbicidal composition in Comparative Example 4 and no free oil separation was observed in the final assessment, after redispersion at 24 h+30 min.

Example 9. Field Test of Herbicidal Activity Against Natural Infestation

[0220] The herbicidal activity of the aqueous emulsions prepared from Examples 1-3 and 6 was evaluated in a field whose floral composition consisted mainly of dicotyledonous weeds (in particular Artemisia vulgaris L., Capsella bursa-pastoris, Taraxacum officinale and Medicago sativa L.) and monocotyledonous weeds (Cynodon dactylon and Poa pratensis), compared with the emulsion prepared from Comparative Examples 4, 5 and 7.

[0221] In order to test this activity on natural infestation, 7.55% v/v dilutions of the compositions in Examples 1-3, 6 and Comparative Example 5, 8% v/v of the composition in Comparative Example 4 and 15.10% v/v of the composition in Comparative Example 7 were prepared, so that an equal dose of active ingredient (10880 g/ha) was distributed over the field using the same volume of aqueous emulsion. In particular, 14.5 L/ha of the aqueous emulsion prepared from the compositions of Examples 1-3, 6 and of Comparative Example 5, 16 L/ha of the aqueous emulsion prepared from the composition of Comparative Example 4 and 29.0 L/ha of the aqueous emulsion prepared from the composition in Comparative Example 7 were distributed. Evaluations of herbicidal activity were carried out at four relevant times, 1, 3, 7 and 12 DAA (day after application) respectively and were conducted according to the standards defined by EPPO (Efficacy evaluation of plant protection products standards PP1/152(4); PP1/181(4)). A visual efficacy evaluation score (% desiccation) was assigned on a scale of 0-100% compared to the untreated control (equal to 0%). The data relating to evaluation of the effectiveness of the treatments was analyzed statistically using ANOVA tests and the means were compared using Tukey tests, for significance levels p≤0.05. The results are shown in Table 5.

TABLE-US-00005 TABLE 5 Table 5. Herbicidal activity against natural infestation (% 0-100 visual rating); Tukey test.sub.a, b p ≤ 0.05, n = 3 Active ingredient dose Measurement I Measurement II Measurement III Measurement IV Emulsions (g/ha) 1 DAA 3 DAA 7 DAA 12 DAA Example 1 10880 86.7 ± 2.9a 83.3 ± 2.9a 76.7 ± 2.9a 75.0 ± 0.0a Example 2 10880 83.3 ± 2.9a  80.0 ± 0.0ab 75.0 ± 0.0a  71.7 ± 2.9ab Example 3 10880 81.7 ± 2.9a 76.7 ± 2.9b 75.0 ± 0.0a 70.0 ± 0.0b Comparative Example 4 10880 70.0 ± 0.0b 70.0 ± 0.0c 66.7 ± 2.9b 60.00 ± 0.0c  Comparative Example 5 10880 79.2 ± 4.5a 70.0 ± 0.0c 65.00 ± 0.0b  60.00 ± 0.0c  Example 6 10880 86.0 ± 4.9a 85.0 ± 0.0a 75.0 ± 0.0a 67.0 ± 4.0b Comparative Example 7 10880 55.8 ± 8.4c  43.3 ± 7.45d 35.0 ± 5.0c 25.0 ± 4.9d

[0222] The results obtained in the field tests show statistically greater herbicidal activity against mono- and dicotyledonous weeds for the aqueous emulsions prepared from Examples 1-3 and 6 than for that prepared from Comparative Example 4 (that doesn't contain anionic and cationic emulsifiers), from Comparative Example 5 (that does not contain anionic emulsifiers) and from Comparative Example 7 (wherein the ratio between the weight content of the sum of anionic surfactants (b) and non-ionic surfactants (d) respect to pelargonic acid is above 0.15). In particular, for the same dose of active ingredient used (10880 g/ha) (Table 5), the herbicidal activity of the compositions according to the invention at 3 days after application was more than 10% higher than that for the Comparative Example 4 and 5, and more than 17% higher after 12 days. In addition, the herbicidal activity of the compositions according to the invention at 3 days after application was more than 40% higher than that for the Comparative Example 7, and more than 50% higher after 12 days.

[0223] The same evaluation was made by repeating the test under field conditions on natural infestation and comparing the herbicidal activity of two aqueous emulsions diluted at 6% and 7.55% v/v prepared from the composition in Example 1, with an 8% v/v dilution prepared from the composition in Comparative Example 4.

[0224] In particular, herbicidal activity was assessed by distributing a dose of 8640 g/ha and 10880 g/ha (using the 6 and 7.55% v/v emulsions according to the invention, respectively) and 10880 g/ha of active ingredient (using the 8% v/v emulsion prepared from the formulation in Comparative Example 4) over the field. The results are shown in Table 6.

TABLE-US-00006 TABLE 6 Table 6. Herbicidal activity against natural infestation (% 0-100 visual rating); Tukey test.sub.a, b p ≤ 0.05, n = 3 Active ingredient Emulsions dose Measurement I Measurement II Measurement III Measurement IV (% v/v) (g/ha) 1 DAA 3 DAA 7 DAA 12 DAA Example 1 (6%) 8640 80 ± 4.1ns 75 ± 4.1b  .sup.   75 ± 4.1ab 70 ± 0.0b Example 1 (7.55%) 10880 90 ± 8.2ns 85 ± 0.0a 81.67 ± 2.4a 80 ± 0.0a Comparative example 4 (8%) 10880 80 ± 4.1ns 75 ± 4.1b 68.33 ± 2.4b 60 ± 0.0c

[0225] The results obtained in the field tests shown in Table 6 show that after the first 12 days following application the herbicidal activity of the emulsion prepared from Example 1 was statistically higher than that in Comparative Example 4, even when using 20% less active ingredient.

Example 10. Evidence of Effectiveness in Tobacco Bud Control

[0226] The efficacy of the aqueous emulsion prepared from Example 1 in controlling tobacco buds was evaluated on plants of the Virginia Bright variety and compared with the emulsion prepared from Comparative Example 4.

[0227] To test such efficacy on tobacco buds, two dilutions of the composition of Example 1 were prepared, at 0.6% and 1% v/v, and one dilution at 1.2% v/v of the composition of Comparative Example 4. In particular, efficacy was assessed by applying 2592 and 4320 g/ha (using the 0.6% and 1% v/v emulsions according to the invention, respectively) and 4896 g/ha of active ingredient (using the 1.2% v/v emulsion prepared from the formulation of Comparative Example 4), respectively.

[0228] The trials were conducted according to EPPO PP standards 1/152(4), 1/135(4), 1/181(4) and 1/155(3). Three applications of each emulsion were carried out, one during pre-flowering (A) and two during post-flowering (B, C).

[0229] In order to evaluate the effectiveness of axillary bud control in tobacco according to EPPO PP 1/155(3), the number of active buds on a total of 5 apical buds was counted at four relevant times. The results are shown in Table 7.

TABLE-US-00007 TABLE 7 Table 7. Percentage of active buds out of the total five apical buds detected 7 days after the first application (7 DAA), 4 days after the second application (4 DAB), 7 and 13 days after the third application (7 DAC and 13 DAC) respectively (p ≤ 0.05, Student-Newman-Keuls). Active ingredient Emulsions dose Measurement I Measurement II Measurement III Measurement IV (% v/v) (g/ha) 7 DAA 4 DAB 7 DAC 13 DAC Example 1 (0.6%) 2592 100 a 84 a 82 a 84 a Example 1 (1%) 4320  43 b 41 b 28 b 28 b Comparative Ex. 4 (1.2%) 4896 100 a 84 a 82 a 84 a

[0230] While the emulsion prepared from Comparative Example 4 showed only a modest activity as a plant growth regulator, since after the third application 82-84% of active shoots were still recorded on the total of the five apical buds (see 7 DAC and 13 DAC), data recorded at the four relevant times showed surprising effectiveness of the 1% v/v emulsion according to the invention. The result is even more surprising if one considers that the concentration of active ingredient was lower than the comparison (1.2% v/v).

[0231] In particular, after the third application, the 1% v/v emulsion according to the invention showed surprisingly high tobacco bud control, with only 28% of the total of five apical buds being active.

[0232] The 0.6% v/v emulsion according to the invention gave comparable results to the comparison, although containing only about half the active ingredient.

Example 11. Evidence of Effectiveness in the Control of Suckers in Grape Vines

[0233] The efficacy of the aqueous emulsion prepared from Example 1 in the control of suckers in grapes vines (Vitis vinifera L.) was compared with the emulsion prepared from Comparative Example 4.

[0234] To test such efficacy, dilutions were prepared, at 7.55% v/v of the composition from Example 1 and at 8.0% v/v of the composition from Comparative Example 4. In particular, efficacy was assessed by applying 10880 g/ha of active ingredient from both the dilutions (of the compositions from Example 1 and from Comparative Example 4).

[0235] The trial was performed according to Good Experimental Practice (GEP). All assessments and applications were done in accordance with the Guidelines: EPPO Standards PP 1/152(4), 1/135(4), 1/181(4), 1/161 (3) and 1/64 (4).

[0236] In order to evaluate the effectiveness of suckers control in grape vines according to EPPO PP 1/161 (3) (Control of suckers in grapevine), two different applications (the first application at the BBCH 55 phenological growth stage of the crop and the second one at the BBCH 67 stage) of each emulsion were carried out in the trial.

[0237] Before the first application, a uniform presence and development of active suckers was observed across the trial area. During the whole trial period, it was evaluated the suckers control recording the percentage of damaged and dead shoots. Evaluations of suckers control activity were carried out at different relevant times, at 22 and 43 DAB, respectively.

[0238] A visual efficacy evaluation score (% desiccation) was assigned on a scale of 0-100% compared to the untreated control (equal to 0%).

[0239] Data from the assessments were analysed by variance analysis (ANOVA). If significant effect of the treatment was obtained (on the basis of the ANOVA analysis) differences between means were checked with Student-Newman-Keuls (SNK) test (P=0.05).

[0240] The results of the trial are shown in Table 8.

TABLE-US-00008 TABLE 8 Table 8. Percentage of suckers control detected at 22 days after the second application (22 DAB) and at 43 days after the second application (43 DAB) respectively (p ≤ 0.05, Student-Newman-Keuls). Active ingredient Emulsions dose Measurement I Measurement II (% v/v) (g/ha) (22-DAB) (43-DAB) Example 1 (7.55%) 10880 62.6 a 44.8 a Comparative Ex. 4 (8%) 10880 43.8 b 36.2 b

[0241] Data of Table 8 show that the aqueous emulsion prepared from Example 1 is more effective than the aqueous emulsion prepared from Comparative Example 4 (62.6% VS 43.8% at 22 DAB and 44.8% VS 36.2% at 43 DAB).

Example 12: Evidence of Effectiveness in the Weed Control in Apple Orchard

[0242] The efficacy of the aqueous emulsion prepared from Example 1 in the weed control in apple orchard cv. Brookfield (Malus domestica Borkh) was compared with the emulsion prepared from Comparative Example 4. In order to test such efficacy, two dilutions of the composition of Example 1 were prepared, at 6.00% and 7.55% v/v, and one dilution at 8.00% v/v of the composition of Comparative Example 4. In particular, the efficacy was assessed by applying 8640 and 10880 g/ha (using the 6.00 and 7.55% v/v emulsions according to the present invention, respectively) and 10880 g/ha of active ingredient (using the 8.00% v/v emulsion prepared from the formulation of Comparative Example 4), respectively.

[0243] The trial was performed according to Good Experimental Practice (GEP). All assessments and applications were done in accordance with the Guidelines EPPO Standards PP 1/152 (4) (Design and analysis of efficacy evaluation trials), 1/135 (4) (Phytotoxicity assessment), 1/181 (4) (Conduct and reporting of efficacy evaluation trials) and 1/90 (3) (Weeds in orchards and other fruiting tree crops such as citrus and olives).

[0244] The trial was set up in order to evaluate the efficacy and selectivity of each emulsion against weeds in apple orchard. The applications were performed twice at crop phenological growth stages BBCH 78 and BBCH 81. At the first timing of application, weed population was determined on the field and the numbers of target weeds per square meter was recorded. Weeds population was homogenous on the field. Evaluations of herbicidal activity were carried out at four relevant times, at 7 and 14 DAA and at 14 and 20 DAB, respectively.

[0245] A visual efficacy evaluation score (% desiccation) was assigned on a scale of 0-100% compared to the untreated control (equal to 0%).

[0246] The results of the trial are shown in Table 9.

TABLE-US-00009 TABLE 9 Table 9. Percentage of herbicidal activity detected at 14 days after the first application (14 DAA) and at 14 days after the second application (14 DAB) respectively (p < 0.05, Student-Newman-Keuls). Active Measurement Measurement ingredient (14-DAA) (14-DAB) Emulsions dose Poa Epilobium Potentilla Poa Epilobium Potentilla (% v/v) (g/ha) annua parviflorum reptans annua parviflorum reptans Example 1 (7.55%) 10880 68.3 a 73.5 a 70.8 a 66.3 a 70.8 a 68.8 a Example 1(6%) 8640 66.8 a 71.5 a 68.8 a 63.0 a 68.5 a  65.8 ab Comparative Ex. 4 (8%) 10880 26.3 b 45.0 b 55.0 b 38.8 b 55.5b  61.3 c

[0247] These results clearly show that emulsions according to the invention (Example 1) are more effective than emulsion from Comparative Example 4 and guarantee a good control also on long term period (at 14 and 20 DAB), even if the concentration of active ingredient is lower than the comparison (8640 g/ha of Example 1 VS 10880 g/ha of Comparative Example 4).

Example 13: Evidence of Effectiveness as Pre-Harvest Desiccant in Potato

[0248] The efficacy as pre-harvest desiccant of the aqueous emulsion prepared from Example 1 was evaluated in potato cv. Mikado, compared with the emulsion prepared from Comparative Example 4.

[0249] In order to test this activity, 6.0 and 7.55% v/v dilutions of the composition from Example 1 and 8% v/v of the composition from Comparative Example 4 were prepared, so that an equal dose of active ingredient of 10880 g/ha for the 7.55% v/v dilution of the composition from Example 1 and 8% v/v of the composition from Comparative Example 4 was distributed over the field using the same volume of aqueous emulsion. In particular, 12.0 and 14.5 l/ha of the emulsions prepared from the composition of Example 1 and 16 l/ha of the emulsion prepared from the composition of Comparative Example 4 were distributed.

[0250] Evaluations of desiccant activity was carried out at 14 DAA (day after application) and was conducted according to the standards defined by EPPO Guidelines PP n. 135 (4) (Phytotoxicity assessment), PP n. 143 (3) (Desiccants used for potato), PP n. 152 (4) (Design and analysis of efficacy evaluation trials) e PP n. 181 (4) (Conduct and reporting of efficacy evaluation trials). A visual efficacy evaluation score (% desiccation) was assigned on a scale of 0-100% compared to the untreated control (equal to 0%). The data relating to evaluation of the effectiveness of the treatments was analyzed statistically using ANOVA tests and the means were compared using Tukey tests, for significance levels p≤0.05. The results of the trial are shown in Table 10.

TABLE-US-00010 TABLE 10 Table 10. Desiccant activity in potato crop (% 0-100 visual rating); Tukey test.sub.a, b p ≤ 0.05, n = 3 Active ingredient dose Measurement I Emulsions (g/ha) 14 DAA Example 1 (6%) 8640 63.6 a Example 1 (7.55%) 10880 67.0 a Comparative Example 4 (8%) 10880 27.8 b

[0251] The results obtained in the field test show statistically greater desiccant activity for the aqueous emulsions prepared from Example 1 than for that prepared from Comparative Example 4 also at the lower dose of active ingredient of 8640 g/ha for the 6.00% v/v dilution of the composition from Example 1.