Benzylpropargylether as nitrification inhibitors

Abstract

The present invention relates to the use of compounds of formula (I) for reducing nitrification and to compositions comprising the compounds of formula (I) and to agricultural mixtures comprising at least one compound of formula (I) and at least one fertilizer. Furthermore, the present invention relates to a method for reducing nitrification comprising treating a plant growing on soil or soil substituents and/or the locus or soil or soil substituents where the plant is growing or is intended to grow with a compound of formula (I) or a composition comprising a compound of formula (I).

Claims

1. An agrochemical mixture comprising: (i) at least one fertilizer selected from the group consisting of a solid or liquid ammonium-containing inorganic fertilizer; a solid or liquid organic fertilizer selected from the group consisting of liquid manure, semi-liquid manure, biogas manure, stable manure, straw manure, worm castings, compost, seaweed or guano; and a urea-containing fertilizer; and (ii) at least one compound of formula (I) ##STR00076## selected from a compound of formula (1-8), a compound of formula (1-15): ##STR00077##

2. A method for reducing nitrification, comprising treating locus or soil or soil substituents where a plant is growing or is intended to grow with a compound of formula (I) ##STR00078## selected from a compound of formula (1-8), a compound of formula (1-15): ##STR00079## wherein: the plant and/or the locus or soil or soil substituents where the plant is growing or is intended to grow is additionally provided with a fertilizer; and the fertilizer is selected from the group consisting of a solid or liquid ammonium-containing inorganic fertilizer; a solid or liquid organic fertilizer selected from the group consisting of liquid manure, semi-liquid manure, biogas manure, stable manure, straw manure, worm castings, compost, seaweed or guano; and a urea-containing fertilizer.

3. The method of claim 2, comprising applying the compound of formula (I) and the and of said fertilizer simultaneously or with a time lag.

4. The method of claim 2, wherein said plant is an agricultural plant selected from the group consisting of wheat, barley, oat, rye, soybean, corn, potatoes, oilseed rape, canola, sunflower, cotton, sugar cane, sugar beet, and rice; a vegetable plant selected from the group consisting of spinach, lettuce, asparagus, cabbages, and sorghum; a silvicultural plant; an ornamental plant; or a horticultural plant, each in its natural or in a genetically modified form.

5. The method of claim 2, wherein the compound of formula (I) is applied as a composition comprising the compound of formula (I) and a carrier.

6. The method of claim 2, wherein the compound of formula (I) is applied as a composition comprising (i) at least one fertilizer; and (ii) at least one compound formula (I).

7. The method of claim 3, comprising applying the compound of formula (I) and the fertilizer with a time lag selected from the group consisting of of 1 day, 2 days, 3 days, 1 week, 2 weeks and 3 weeks.

8. The agrochemical mixture of claim 1, wherein said fertilizer is a solid or liquid ammonium-containing inorganic fertilizer selected from the group consisting of an NPK fertilizer, ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate or ammonium phosphate.

9. The agrochemical mixture of claim 1, wherein said fertilizer is a urea-containing fertilizer selected from the group consisting of urea, formaldehyde urea, urea ammonium nitrate (UAN) solution, urea sulphur, stabilized urea, urea based NPK-fertilizers, or urea ammonium sulfate.

10. The method of claim 2, wherein said fertilizer is a solid or liquid ammonium-containing inorganic fertilizer selected from the group consisting of an NPK fertilizer, ammonium nitrate, calcium ammonium nitrate, ammonium sulfate nitrate, ammonium sulfate or ammonium phosphate.

11. The method of claim 2, wherein said fertilizer is a urea-containing fertilizer selected from the group consisting of urea, formaldehyde urea, urea ammonium nitrate (UAN) solution, urea sulphur, stabilized urea, urea based NPK-fertilizers, or urea ammonium sulfate.

Description

EXAMPLES

Example 1

(1) The compounds of the invention have been tested as follows in terms of the inhibition of nitrification:

(2) Soil was sampled fresh from a field (e.g. Limburgerhof), dried and sieved through a 500 μm sieve. Approximately 200 mg of soil were placed into each well of a 48 well plate. Compounds, or DMSO alone, were added at a concentration of 10 ppm, dissolved in 1% DMSO. 6 μmol ammonium sulfate was added per well as well as 4.8 mg NaClO.sub.3.

(3) Subsequently, the samples were incubated at room temperature for up to 72 hrs. After the incubation period 64 mg KCl were added and mixed. 25 μl of the supernatant were placed into a fresh plate and 260 μl of a color reaction solution (from Merck Nr 1.11799.0100) were added. Measurements were taken with a Tecan plate Reader at 540 nm wavelength.

(4) The results of the measurements (with a dose of 10 ppm) were that all compounds 1-1 to 1-22 as shown in Table 1 above, supra demonstrated an inhibition of ≥10% compared to a control (DMSO only). Futhermore, the compounds 1-23 to 1-33 as shown in Table 1 above (with a dose of 5±1 ppm), supra demonstrated an inhibition of 15% compared to a control (DMSO only). Inhibition is calculated as x=% activity compared to control, and converted to 100-x to give the value of inhibition, rather than activity.

Example 1.1

(5) The results for the compounds tested with a dose of 10 ppm are provided in the following Table 1.1. In each case, the best inhibition value (IN) obtained for a compound is provided.

(6) TABLE-US-00002 TABLE 1.1 No. Compound IN 1-1 15 1-2 48 1-3 11 1-4 15 1-5 27 1-6 10 1-7 11 1-8 57 1-9 0 20 1-10 14 1-11 12 1-12 15 1-13 10 1-14 56 1-15 58 1-16 11 1-17 10 1-18 10 1-19 0 15 1-20 10 1-21 20 1-22 11

Comparative Example 1.2

(7) For comparative purposes phenylacetylene was tested under the same conditions as outlined above with a dose of 10 ppm. The following inhibition value was obtained.

(8) TABLE-US-00003 TABLE 1.2 Comp. Ex.1.2 Structure IN Phenylacetylene 7

Example 1.3

(9) The results for the compounds tested with a dose of 5±1 ppm are provided in the following Table 1.3. In each case, the best inhibition value (IN) obtained for a compound is provided.

(10) TABLE-US-00004 TABLE 1.3 No. Compound IN 1-23 18 1-24 18 1-25 87 1-26 69 1-27 59 1-28 0 88 1-29 37 1-30 25 1-31 18 1-32 53 1-33 24