COMPOSITION COMPRISING A PESTICIDE AND AN ALKOXYLATED ESTER

Abstract

A composition comprising a pesticide and alkoxylated ester is provided, as well as seed including the composition. Use of alkoxylated esters as adjuvants in pesticide-comprising spray mixtures are also described. Methods for controlling phytopathogenic fungi and/or undesirable plant growth and/or undesirable insect or mite infestation and/or for regulating the growth of plants are further provided, wherein the composition is allowed to act on the respective pests, the habitat thereof or the plants to be protected from the respective pest, on the soil and/or on undesirable plants and/or the crop plants and/or the habitat thereof.

Claims

1. A composition comprising a pesticide and at least one of an alkoxylated ester of the general formula (I) ##STR00003## and an alkoxylated ester of the general formula (II) ##STR00004## where R.sup.1, R.sup.4, R.sup.6 and R.sup.7 each independently are a linear or branched alkyl having 5 to 18 carbon atoms, a linear or branched alkenyl having 5 to 18 carbon atoms, a heteroalkyl having 3 to 18 carbon atoms or a heteroalkenyl having 3 to 18 carbon atoms; R.sup.2 and R.sup.3 each independently are selected from the group consisting of ethylene, propylene, butylene, and a mixture thereof; X is a single bond, a saturated or unsaturated, linear or branched alkylene having 1 to 14 carbon atoms, a cycloalkylene having 4 to 14 carbon atoms, a saturated or unsaturated, linear or branched heteroalkylene having 1 to 14 carbon atoms or a heterocycloalkylene having 4 to 14 carbon atoms; R.sup.5 is selected from the group consisting of a saturated or unsaturated, linear or branched alkylene having 1 to 14 carbon atoms, a cycloalkylene having 4 to 14 carbon atoms, a saturated or unsaturated, linear or branched heteroalkylene having 1 to 14 carbon atoms, and a heterocycloalkylene having 4 to 14 carbon atoms; and n has a value of from 1 to 100.

2. The composition according to claim 1, wherein R.sup.1, R.sup.4, R.sup.6 and R.sup.7 each independently are selected from the group consisting of: a linear or branched alkyl, alkenyl, heteroalkyl or heteroalkenyl having 8 to 14 carbon atoms.

3. The composition according to claim 1, wherein R.sup.1, R.sup.4, R.sup.6 and R.sup.7 each independently are one of a linear alkyl having 8 to 12 carbon atoms and a hetereoalkyl having 8 to 12 carbon atoms.

4. The composition according claim 1, wherein R.sup.2 is one of ethylene and a mixture of ethylene and propylene.

5. The composition according claim 1, wherein R.sup.2 is ethylene.

6. The composition according to claim 1, wherein X is selected from the group consisting of a saturated, linear alkylene having 4 carbon atoms, a cycloalkylene having 6 carbon atoms, a heterocyclolalkylene having 4 carbon atoms and 1 oxygen atom, a heterocyclolalkylene having 4 carbon atoms and 2 nitrogen atoms, and furanyl.

7. The composition according to claim 1, wherein R.sup.5 is selected from the group consisting of a saturated, linear alkylene having 4 carbon atoms, a cycloalkylene having 6 carbon atoms, a heterocyclolalkylene having 4 carbon atoms and 1 oxygen atom, a heterocyclolalkylene having 4 carbon atoms and 2 nitrogen atoms, and furanyl.

8. The composition according to claim 1, wherein n has a value of from 3 to 50.

9. The composition according to claim 1, wherein the pesticide comprises one of: at least one fungicide, at least one herbicide, and at least one insecticide.

10. The composition according to claim 9, wherein the fungicide is selected from carboxamides, triazoles and strobilurins.

11. A method of preparing the composition as defined in claim 1, the method comprising bringing the pesticide and the alkoxylated ester of one of the general formula (I) and (II) into contact.

12. A method for at least one of (i) controlling at least one of: phytopathogenic fungi, undesirable plants, undesirable pest infestation, and (ii) regulating the growth of at least one of undesired plants and crop plants, the method comprising applying the composition as defined in claim 1 on at least one of (a) the pests, (b) the environment of the pests, (c) the crop plants to be protected from the pests, (d) soil associated with at least one of the pests and the crop plants to be protected from the pests, (e) undesired plants, (f) the crop plants, (g) the environment of at least one of the undesired plants and the crop plants.

13. Seed comprising the composition as defined in claim 1.

14. (canceled)

15. (canceled)

Description

EXAMPLES

Example 1Synthesis of Alkoxylated Ester

[0111] The following alkoxylated esters were obtained by the method described below:

[0112] Di-Isononanyl-3EO-Adipate

[0113] 2.26 mol of Isononanol+3EO was esterified with 1.13 mol of adipic acid using 0.03% of Tin-oxalate (Tegokat 160 obtainable by Goldschmidt Industrial Chemical Corp or Tibcat 160 obtainable by TIB Chemicals) at 160-220 C. until the calculated amount of water (2.26 mol) was removed by applying vacuum down to 50 mbar or even less. The final ester was bleached and filtrated by using Tonsil filter aid (obtainable by Sid-Chemie AG, Germany) at 95 C. and a Seitz pressure filter with a K800 filter sheet (obtainable by Seitz-Schenk Fildersystems GmbH, Germany).

[0114] 1,2-Cyclohexanediol-6EO-Di-Isononate

[0115] 1,2-Cyclohexanediol-6EO-di-isononate was produced in the same manner as Di-isononanyl-3EO-adipate by esterification of 1 mol 1,2-Cyclohexandiol+6EO with 2 mol Isononanoic acid at 160-220 C. until the calculated amount of water (2.26 mol) was removed by applying vacuum down to 50 mbar or even less. The final ester was bleached and filtrated by using Tonsil filter aid (obtainable by Sid-Chemie AG, Germany) at 95 C. and a Seitz pressure filter with a K800 filter sheet (obtainable by Seitz-Schenk Fildersystems GmbH, Germany).

[0116] Cyclohexanedicarboxylic Acid-Isononanol-3EO-Diester

[0117] 1 mol of cyclohexane dicarboxylic acid was esterified with 2 mol of Isononanol+3EO by using 0.5% methanesulfonic acid and 0.4% of hypophosphoric acid at 160-230 C. until the desired amount of 2 mol of water was distilled off by applying vacuum down to 50 mbar. The final product was treated with 1% of activated charcoal and PRIMISIL 141 filter aid (obtainable by Sd-Chemie AG, Germany).

Example 2Green House Trials

[0118] The influence of the adjuvants was tested separately in a curative and protective greenhouse trial on barley. In each case, barley was cultivated in a substrate Frustorder Erde for three weeks with three plants per pot. Each treatment was replicated 14 times. The adjuvant dose rate in each treatment was 50 ml/ha. The assessment of the infection rate was conducted by a trained biologist.

[0119] The adjuvants used in the trials are di-isononanyl-adipate cyclohexanedicarboxylic acid-isononanol-diester, 1,2-cyclohexanediol-di-isononate, di-isononanyl-3EO-adipate, cyclohexanedicarboxylic acid-isononanol-3EO-diester and 1,2-cyclohexanediol-6EO-di-isononate.

[0120] Curative Trial with Epoxiconazole:

[0121] An Epoxiconazole SC 250 was used. Inoculation of the leaves with powdery mildew (Blumeria graminis f. sp. hordei) was done 2 days prior to application of the Epoxiconazole formulation. From the stem, 15 leaf segments were cut off with a length of 10 cm using each the flag leaf (F) and the 2nd leaf (F-1). Altogether, the leaves of each were placed on benzimidazole agar i.e. 0.5% Agar with 40 ppm benzimidazole. The concentration of Epoxiconazole for the leaf application was 5 g/ha. Assessment was done 14 days after treatment (14 DAT) of the efficacy against powdery mildew by counting the mildew pustules per leaf on a length of 7 cm.

[0122] Protective Trial with Azoxystrobin:

[0123] 4 h after application with the equivalent of 5 g/ha Azoxystrobin, leaf segments were cut off at a length of 7 cm from the stem. 15 leaves of each the F and the F-1 leaf were placed on agar. After the inoculation with powdery mildew (Blumeria graminis f. sp. hordei), the incubation time was 10 d. The assessment of the infection rate was conducted by a trained biologist.

[0124] Results

TABLE-US-00001 TABLE 1 Curative Trial Powdery mildew Composition infestation (%) Without Epoxiconazole and Adjuvant* 79 Epoxiconazole* 33 Epoxiconazole + Di-isononanyl-adipate* 29 Epoxiconazole + Di-isononanyl-3EO- 3 adipate Epoxiconazole + Cyclohexanedicarboxylic 21 acid-isononanol-diester* Epoxiconazole + Cyclohexanedicarboxylic 16 acid-isononanol-3EO-diester Epoxiconazole + 1,2-Cyclohexanediol-di- 28 isononate* Epoxiconazole + 1,2-Cyclohexanediol- 15 6EO-di-isononate *Comparative Examples

[0125] This trial shows that mildew infestation can be significantly reduced by adding the alkoxylated esters of the present invention as compared to the active Epoxiconazole alone or more importantly as compared to the non alkoxylated esters.

TABLE-US-00002 TABLE 2 Protective Trial Powdery mildew Composition infestation (%) Without Azoxystrobin and Adjuvant* 84 Azoxystrobin* 36 Azoxystrobin + Di-isononanyl-adipate* 27 Azoxystrobin + Di-isononanyl-3EO- 3 adipate Azoxystrobin + Cyclohexanedicarboxylic 24 acid-isononanol-diester* Azoxystrobin + Cyclohexanedicarboxylic 17 acid-isononanol-3EO-diester Azoxystrobin + 1,2-Cyclohexanediol-di- 29 isononate* Azoxystrobin + 1,2-Cyclohexanediol-6EO- 16 di-isononate *Comparative Examples

[0126] This trial shows that mildew infestation can be significantly reduced by adding the alkoxylated esters of the present invention as compared to the active Azoxystrobin alone or more importantly as compared to the non alkoxylated esters.