EMULSIFIABLE CONCENTRATE CONTAINING ALLYL ISOTHIOCYANATE AND ITS USE AS A NEMATICIDE IN CROP PLANTS

Abstract

The present invention relates to an agrochemical emulsifiable concentrate comprising: —allyl isothiocyanate; —at least one vegetable oil; —at least one non-ionic surfactant; —at least one anionic surfactant. The present invention also relates to the use of the above emulsifiable concentrate as a nematicide in crop plants.

Claims

1. An agrochemical emulsifiable concentrate comprising: allyl isothiocyanate; at least one vegetable oil; at least one non-ionic surfactant; at least one anionic surfactant.

2. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one vegetable oil is selected from: rapeseed oil, soybean oil, olive oil, castor oil, linseed oil, including derivatives thereof esterified with C1-C6 alkyl groups.

3. The agrochemical emulsifiable concentrate according to claim 1, wherein said vegetable oil is rapeseed oil, preferably a C1-C6 ester of the rapeseed oil.

4. The agrochemical emulsifiable concentrate according to claim 1, wherein said allyl isothiocyanate is present in an amount comprised in the range between 1% and 70% by weight with respect to the weight of said emulsifiable concentrate.

5. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one vegetable oil is present in an amount in the range between 1% and 90% by weight with respect to the weight of said emulsifiable concentrate.

6. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one non-ionic surfactant is selected from the group consisting of: ethoxylated block copolymers, etho-propoxylated block copolymers, ethoxylated tristyrylphenols, etho-propoxylated tristyrylphenols, ethoxylated tristyrylphenol phosphates (acid form), ethoxylated tristyrylphenol sulphates (acid form), sorbitan monolaurates, ethoxylated sorbitan monolaurates, sorbitan mono-oleates, ethoxylated sorbitan mono-oleates, ethoxylated vegetable oil, ethoxylated fatty alcohols, organosilicon compounds and mixtures thereof.

7. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one non-ionic surfactant is present in the emulsifiable concentrate in an amount in the range from 1% to 20% by weight with respect to the weight of said emulsifiable concentrate.

8. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one anionic surfactant is selected from the group consisting of: ethoxylated tristyrylphenol phosphates (salified form), ethoxylated tristyrylphenol sulphates (salified form), calcium dodecyl benzene sulphonate and mixtures thereof.

9. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one anionic surfactant is present in the emulsifiable concentrate in an amount in the range from 1% to 20% by weight with respect to the weight of said emulsifiable concentrate.

10. The agrochemical emulsifiable concentrate according to claim 1 comprising, by weight with respect to the weight of the emulsifiable concentrate: 5%—45% by weight of allyl isothiocyanate; 5%—15% by weight of at least one non-ionic surfactant; 1%—10% by weight of at least one anionic surfactant; 1%—90% of at least one vegetable oil.

11. A process for preparing an agronomic formulation in the form of an oil-in-water emulsion comprising: providing at least one agrochemical emulsifiable concentrate according to claim 1, diluting said emulsifiable concentrate with water to obtain said agronomic formulation in the form of an oil-in-water emulsion.

12. A method for controlling nematodes in a crop plant comprising applying at least one effective dose of an agrochemical emulsifiable concentrate according to claim 1 to a crop plant, said concentrate being applied in undiluted form or in diluted form with water to form an oil-in-water emulsion.

13. (canceled)

14. The agrochemical emulsifiable concentrate according to claim 1, wherein said allyl isothiocyanate is present in an amount in the range between 5% and 45% by weight with respect to the weight of said emulsifiable concentrate.

15. The agrochemical emulsifiable concentrate according to claim 1, wherein said allyl isothiocyanate is present in an amount in the range between 15 and 25% by weight with respect to the weight of said emulsifiable concentrate.

16. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one vegetable oil is present in an amount in the range between 40% and 70% by weight with respect to the weight of said emulsifiable concentrate.

17. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one non-ionic surfactant is present in the emulsifiable concentrate in an amount in the range from 5% to 15% by weight with respect to the weight of said emulsifiable concentrate.

18. The agrochemical emulsifiable concentrate according to claim 1, wherein said at least one anionic surfactant is present in the emulsifiable concentrate in an amount in the range from 1% to 10% by weight with respect to the weight of said emulsifiable concentrate.

19. The agrochemical emulsifiable concentrate according to claim 10, wherein said allyl isothiocyanate is present in the emulsifiable concentrate in an amount in the range of from 15%-25% by weight with respect to the weight of the emulsifiable concentrate.

Description

EXAMPLES

Example 1

Emulsifiable Concentrate Containing Allyl Isothiocyanate

[0053] The emulsifiable concentrate IRF265-2 was prepared according to the present invention, having the composition shown in Table 1.

[0054] The commercial products used for the preparation of the aforementioned oil dispersions are as follows: [0055] Amesolv CME, mixture of methyl esters of rapeseed oil fatty acids; [0056] Soprophor 796/P, etho-propoxylated tristyrylphneol; [0057] Rhodacal 60/BE, calcium salt of benzene sulphonic acid.

TABLE-US-00001 TABLE 1 IRF265-2 Components % by weight Allyl isothiocyanate (99.5% 20 technical) Amesolv CME (vegetable oil) 65 Rhodacal 60/BE (anionic surfactant) 5 Soprophor 796/P (non-ionic 10 surfactant) TOTAL 100

[0058] The emulsifiable concentrate IRF265-2 was subjected to the accelerated stability test according to Cipac MT 46.1, which aims to accelerate the ageing of a product by heating. This test makes it possible to simulate the stability of a formulation after two years of storage at room temperature.

[0059] The following procedure was used: a certain amount of formulation (for example 500 mL) was placed in a hermetically sealed container and left in a heater at 54° C. for 14 days. After this time, the container was removed from the heater and left to return to room temperature. It was therefore visually verified that the formulation did not demonstrate any phase separation or other phenomena of physical instability, such as flocculation, aggregation or crystalline growth. The chemical stability of the active agrochemical ingredient is also verified, as well as the quality of the dispersion subjected to accelerated stability tests, after dilution in water.

[0060] The IRF265-2 sample passed the accelerated ageing test, having remained in a homogeneous state at the end of the heat treatment.

Example 2

Determination of Nematicide Activity against Phytoparasitic Nematodes

[0061] The tests aimed at testing the nematicidal activity of the products under examination were carried out in protected cultivation conditions or in the open field, in soils naturally infested with species of phytoparasitic nematodes. A qualitative-quantitative evaluation of the presence of parasites was carried out by taking and analysing soil samples before the start of the experiments.

[0062] The tested products were all applied by fertigation, with hoses having a diameter of 16 mm and a distance between the dispensing holes of 10 cm, connected to a layflat spread on the ground along the entire length of the treated area. The layflat was connected to a pump which withdrew water from the irrigation system and mixed it directly with the product with the Venturi system. Pressure gauges connected at the beginning and end of the layflat allowed to check the water pressure inside the treatment system. The hoses, spread perpendicular to the layflat, were covered with a plastic sheet suitable for the application of fumigant products. Before the treatment, the soil was suitably irrigated, to facilitate the dispersion of the active ingredients in the soil.

[0063] The following products were tested: [0064] emulsifiable concentrate IRF265-2 of example 1; [0065] Dominus™, commercial fumigant containing 96.3% AITC by weight; [0066] Vapam™, commercial fumigant containing Metam-sodium at 38.8% by weight.

[0067] The tested products were applied, after dilution with water, on bare soil: IRF265-2 and Dominus™ 14 days before sowing or transplanting; Vapam™ according to its label.

[0068] The evaluation of the performance of the products comprised: the detection of any phytotoxic effects (using a zero-ten scale where: zero=no symptoms, 10=destroyed plant), the determination of the growth of the plants (measured with a scale of 1-5 or through the NDVI “normalized difference vegetation index”) and effectiveness against the nematode (by analysing the number of J2 larvae present in the soil or by using the Bridge & Page scale to evaluate the root-knot nematode infestation index of the root system).

[0069] The following tables show the data collected in tests conducted on different crops and species of nematodes (1 US gal/acre=9.35 l/ha).

[0070] Table 2 shows the results of a test on an onion infested with Meloidogyne spp.

TABLE-US-00002 TABLE 2 PLANT n. J2 APPLIED PHYTO- GROWTH LARVAE DOSE TOXICITY (NDVI IN THE COMPOUND (gal/acre) (scale 0-10) index) SOIL CONTROL — — 0.5 109 INFESTED IRF265-2 20 0 0.7 85 30 0 0.8 62 40 0 0.8 60 DOMINUS ™ 30 0 0.8 65 VAPAM ™ 40 0 0.7 78

[0071] Table 3 shows the results of a test on a potato infested with Meloidogyne chitwoodi.

TABLE-US-00003 TABLE 3 APPLIED PHYTO- PLANT LARVE J2 DOSE TOXICITY GROWTH IN THE COMPOUND (gal/acre) (scale 0-10) (scale 1-10) SOIL CONTROL — — 5 115 INFESTED IRF265-2 20 0 7 82 30 0 8 60 40 0 8 65 DOMINUS ™ 30 0 8 70 VAPAM ™ 40 0 7 85

[0072] Table 4 shows the results of a test on a potato infested with Pratylenchus coffeae.

TABLE-US-00004 TABLE 4 APPLIED PHYTO- PLANT LARVE J2 DOSE TOXICITY GROWTH IN THE COMPOUND (gal/acre) (scale 0-10) (scale 1-5) SOIL CONTROL — — 2 505 INFESTED IRF265-2 20 0 3 189 30 0 3.5 150 40 0 3.5 155 DOMINUS ™ 30 0 3.5 160 VAPAM ™ 40 0 3 185

[0073] Table 5 shows the results of a test on a cucumber infested with Meloidogyne incognita.

TABLE-US-00005 TABLE 5 ROOT- KNOT APPLIED PHYTO- PLANT NEMATODE DOSE TOXICITY GROWTH INDEX COMPOUND (gal/acre) (scale 0-10) (scale 1-5) (scale 0-10) CONTROL — — 1.5 9 INFESTED IRF265-2 5 0 3 6 10 0 3.5 4 20 0 4 3.5 DOMINUS ™ 10 0 3.5 4 VAPAM ™ 40 0 3 5

[0074] From the results obtained in the experiments conducted against different nematodes and on different crops, it can be concluded that the product IRF265-2 according to the invention demonstrates efficacy and selectivity fully comparable to the commercial product Dominus™ when applied to the same dose of formulation, although it contains only 20% of the agrochemical active ingredient allyl isothiocyanate.

Example 3

Stability Test

[0075] The emulsifiable concentrate IRF265-2 was subjected to a further stability test (according to Cipac MT 36) to evaluate the stability of an oil-in-water emulsion of the product after 24 hours. For comparison, some emulsifiable concentrates containing solvents other than vegetable oil were also prepared (Ref.1-Ref.3), which were subsequently subjected to the same stability test. The compositions of the prepared and tested emulsifiable concentrates are shown in table 6.

TABLE-US-00006 TABLE 6 IRF265-2 Ref. 1 Ref. 2 Ref. 3 % by % by % by % by Components weight weight weight weight Allyl isothiocyanate 20 20 20 20 (99.5% technical) Amesolv CME 65 — — — Soprophor 796/P 10 10 10 10 Rhodacal 60/BE 5 5 5 5 Propylene glycol — 65 — — Mineral oil — — 65 — Butyl lactate — — — 65 TOTAL 100 100 100 100

[0076] For the stability test, the emulsifiable concentrates were poured at a concentration of 5% v/v in standard D Cipac water (hardness 342 ppm), as per the test MT 36. The following procedure was used: fill a 100 ml graduated glass cylinder with 95 ml of standard Cipac D water, add 5 ml of EC formulation and stop the cylinder with a glass stopper. The cylinder is inverted 30 times and left undisturbed at 30° C., observing the stability of the emulsion formed after 30 minutes, 2 hours and 24 hours. The observations relating to the stability of these emulsifiable concentrates after 30 minutes, 2 hours and 24 hours are reported in table 7.

TABLE-US-00007 TABLE 7 IRF265-2 Ref. 1 Ref. 2 Ref. 3 After 30 Stable Oil Oil stable min separation separation After 2 Stable 5 mL oil 5 mL oil 2-3 mL oil h separation separation separation and emulsion non- homogeneity After 24 Stable n.d. n.d. 2-3 mL oil h separation

[0077] The term “stable” means that no separation of oil or non-homogeneity is detected in the emulsion. The term “n.d.” stands for not determined.

[0078] As can be seen from table 7, the emulsifiable concentrate IRF265-2 according to the invention is stable even after 24 hours, while the comparative ones are already unstable after 2 hours.