Composition comprising a pesticide, a surfactant and an alkoxylate of 2-propyheptylamine

Abstract

The present invention relates to a composition comprising a pesticide, a surfactant and an alkoxylate. Moreover, the invention relates to a concentrate comprising the surfactant and the alkoxylate; and to a process for preparing the composition by bringing into contact the concentrate and a pesticide; or by bringing into contact the pesticide, the surfactant and the alkoxylate; and to the use of the surfactant by addition to a mixture comprising the pesticide and the alkoxylate. The invention furthermore relates to a method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition is allowed to act on the respective pests, their environment 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 their environment. Furthermore, the invention relates to seed comprising the composition.

Claims

1. A composition comprising a pesticide, a surfactant and an alkoxylate, wherein the alkoxylate is an amine alkoxylate (A) ##STR00005## or a quaternized derivative (AQ) ##STR00006## of the amine alkoxylate (A), where R.sup.1O.sub.n, R.sup.2O.sub.m, and R.sup.5O.sub.p and independently of one another are alkoxylate chains comprising ethylene oxide, propylene oxide, butylene oxide or a mixture thereof, R.sup.3 is an H, —OH, —OR.sup.4, —[R.sup.5—O].sub.p—R.sup.6, C.sub.1-C.sub.6-alkyl or an oxygen anion, R.sup.4 is a C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, R.sup.6 is an H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, —SO.sub.3R.sup.a, —P(O)OR.sup.bOR.sup.c, —CH.sub.2CO.sub.2R.sup.d, or —C(O)R.sup.e, R.sup.7 is 2-propylheptyl, R.sup.a and R.sup.d independently of one another are an H, inorganic or organic cations, R.sup.b and R.sup.c independently of one another are an H, inorganic or organic cations, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, R.sup.e is C.sub.1-C.sub.22-alkyl, C.sub.2-C.sub.22-alkenyl, C.sub.2-C.sub.22-alkynyl, C.sub.6-C.sub.22-aryl or C.sub.7-C.sub.22-alkylaryl, n, m and p independently of one another have a value of from 1 to 30, A.sup.− is an agriculturally acceptable anion, or, if R.sup.3 is an oxygen anion, A.sup.− is absent; and wherein at least one surfactant is selected from the group of surfactants consisting of a) a C.sub.6-18-alkylpolyglucoside, with a degree of polymerization of from 1.2 to 1.9, and b) a C.sub.8-18-alkylbenzenesulfonate.

2. The composition according to claim 1, wherein the weight ratio of surfactant to alkoxylate is in the range of from 1:99 to 70:30.

3. The composition according to claim 1, wherein the composition comprises from 1 to 80% by weight of the total of surfactant and alkoxylate.

4. The composition according to claim 1, wherein the composition comprises at least two different surfactants.

5. A composition comprising a pesticide, a surfactant and an alkoxylate, wherein the alkoxylate is an amine alkoxylate (A) ##STR00007## or a quaternized derivative (AQ) ##STR00008## of the amine alkoxylate (A), where R.sup.1O.sub.n, R.sup.2O.sub.m, and R.sup.5O.sub.p and independently of one another are alkoxylate chains comprising ethylene oxide, propylene oxide, butylene oxide or a mixture thereof, R.sup.3 is an H, —OH, —OR.sup.4, —[R.sup.5—O].sub.p—R.sup.6, C.sub.1-C.sub.6-alkyl or an oxygen anion, R.sup.4 is a C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, R.sup.6 is an H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, —SO.sub.3R.sup.a, —P(O)OR.sup.bOR.sup.c, —CH.sub.2CO.sub.2R.sup.d, or —C(O)R.sup.e, R.sup.7 is 2-propylheptyl, R.sup.a and R.sup.d independently of one another are an H, inorganic or organic cations, R.sup.b and R.sup.c independently of one another are an H, inorganic or organic cations, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl or C.sub.2-C.sub.6-alkynyl, R.sup.e is C.sub.1-C.sub.22-alkyl, C.sub.2-C.sub.22-alkenyl, C.sub.2-C.sub.22-alkynyl, C.sub.6-C.sub.22-aryl or C.sub.7-C.sub.22-alkylaryl, n, m and p independently of one another have a value of from 1 to 30, A.sup.− is an agriculturally acceptable anion, or, if R.sup.3 is an oxygen anion, A.sup.− is absent; wherein the surfactant is selected from the group consisting of: a) a C.sub.16-18-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and/or propylene oxide, and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 12 to 35; b) a C.sub.10-guerbet alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 8; c) an iso-C.sub.13-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 3 to 10; d) a C.sub.4-8-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 9; and g) a phosphate ester of C.sub.8-14-alkanol alkoxylates.

6. The composition according to claim 1, wherein at least one surfactant is a C.sub.8-10-alkylpolyglucoside with a degree of polymerization of from 1.4 to 1.9.

7. The composition according to claim 1, wherein R.sup.1, R.sup.2 and R.sup.5 independently of one another are ethylene, ethylene and propylene, ethylene and butylene, or ethylene, propylene and butylene.

8. The composition according to claim 1, wherein the pesticide is a pesticide with at least one H-acidic group or an anionic salt of the pesticide with at least one H-acidic group.

9. The composition according to claim 1, wherein, in the amine alkoxylate (A), the total of n and m is from 2 to 40, and in its quaternized derivative (AQ) the total of n, m and p is from 3 to 80.

10. The composition according to claim 1, wherein R.sup.3 is an H.

11. The composition according to claim 1, wherein the pesticide comprises a pesticide with at least one H-acidic group.

12. A concentrate comprising the composition according to claim 1.

13. A method of controlling phytopathogenic fungi and/or undesired vegetation and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition according to claim 1 is allowed to act on the respective pests, their environment or the plants to be protected from the respective pest, on the soil and/or on undesired plants and/or the crop plants and/or their environment.

14. The method according to claim 13, wherein the surfactant is an anionic surfactant comprising an anionic group, which is a sulfonate, sulfate, phosphate or carboxylate; and/or a nonionic surfactant, which is a sugar-based surfactant or an alkanol alkoxylate.

15. The method according to claim 13, wherein the weight ratio of surfactant to alkoxylate is in the range of from 1:99 to 70:30.

16. The method according to claim 13, wherein the composition comprises from 1 to 80% by weight of the total of surfactant and alkoxylate.

17. The method according to claim 13, wherein the composition comprises at least two different surfactants.

18. The method according to claim 13, wherein at least one surfactant is selected among the following surfactants: a) a C.sub.16-18-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and/or propylene oxide, and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 12 to 35; b) a C.sub.10-guerbet alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 8; c) an iso-C.sub.13-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 3 to 10; d) a C.sub.4-8-alkanol alkoxylate, where the alkoxylate is composed of ethylene oxide and the alkanol alkoxylate has a mean number of alkoxide units in the range of from 2 to 9; e) a C.sub.8-10-alkylpolyglucoside, with a degree of polymerization of from 1.4 to 1.9; f) a C.sub.8-14-alkylbenzenesulfonate; and g) a phosphate ester of C.sub.8-14-alkanol alkoxylates.

19. Seed treated with the composition according to claim 1.

20. The composition according to claim 1, wherein the pesticide is a pesticide with at least one H-acidic group or an anionic salt of the pesticide with at least one H-acidic group, selected from the group consisting of glyphosate, glufosinate, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin and imazethapyr.

21. The composition according to claim 1, wherein the C.sub.8-18-alkylbenzenesulfonate is a C.sub.10-13-alkylbenzenesulfonate.

Description

EXAMPLES

(1) Surfactant A: C.sub.10-13-alkylbenzenesulfonate, free acid. Surfactant B: Phosphate ester of C.sub.10-12-alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and/or propylene oxide, and having a mean number of alkoxide units in the range of from 12 to 18. Surfactant C: C.sub.16-18-alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and propylene oxide, and having a mean number of alkoxide units in the range of from 17 to 26. Surfactant D: iso-C.sub.13-alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 4.5 to 8. Surfactant E: C.sub.10-guerbet alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 2.5 to 6. Surfactant F: C.sub.4-8-alkanol alkoxylate, the alkoxylate being composed of ethylene oxide and having a mean number of alkoxide units in the range of from 3.5 to 7. Surfactant G: Fatty acid mixture comprising 50-60% dodecanoic acid and 20-30% of C.sub.14-alkanolic acid, and further C.sub.10-18-alkanoic acids, acid number 250-260. Surfactant H: C.sub.8-10-alkylpolyglucoside, D.P. 1.7.

Example 1

Preparation of Amine Alkoxylate A

(2) First, 2-propylheptylamine was prepared starting from 2-propylheptanol and ammonia, as described in Example 1 of PCT/EP2011/050369.

(3) Then 1280 g (8.15 mol) of the 2-propylheptylamine were admixed with 40 g of water. Then, after flushing with nitrogen, at 100° C., 717 g (16.3 mol) of ethylene oxide were metered in (2 bar, 16 h). Subsequently, at 90° C., remaining traces of ethylene oxide were removed under reduced pressure. This gave a quantitative yield with an amine number of 229 mg KOH/g. In the next step, 821.5 g (3.35 mol) of this precursor product were admixed with 8.0 g of 50% strength KOH and dewatering was carried out at 90° C. under reduced pressure. After flushing with nitrogen, at 120° C., 1179 g (=26.8 mol) of ethylene oxide were metered in (1.5 bar, 12 h). This gave a quantitative yield of the yellowish low-viscosity, liquid amine-alkoxylate A.

Example 2

Amine Alkoxylate+Surfactant A

(4) For the greenhouse tests, winter wheat (cultivar Cubus) and soybean (cultivar Oxford) were sown or potted in loamy sandy soil to a depth of 1-2 cm. When the plants had reached a growth height of 10 to 25 cm (i.e., around 10 to 21 days after sowing), the spray mixtures were applied to the plants in a spraying cabin.

(5) A concentrated formulation comprising glyphosate isopropylammonium in solution in water comprising the surfactants stated and amine alkoxylate A from Example 1 was diluted with deionized water and applied at a water application rate of 375 l/ha (140 g or 280 g of glyphosate/ha). The temperatures in the experimental period were between 18-35° C. During this time, the experimental plants received optimum watering, with nutrients being supplied via the water used for watering.

(6) The herbicidal activity was evaluated by awarding scores to the treated plants (four each time) in comparison to the untreated control plants. The evaluation scale ranges from 0% to 100% activity. 100% activity means the complete death at least of those parts of the plant that are above ground. Conversely, 0% activity means that there were no differences between treated and untreated plants.

(7) The results in Tables 1 demonstrate the increased activity of the active substance as a result of addition of the amine alkoxylate in admixture with surfactant.

(8) TABLE-US-00001 TABLE 1A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Without .sup.a) — 53 10 Amine alkoxylate A .sup.a) 300 85 62 Surfactant A .sup.a) 300 84 64 Amine alkoxylate A + 255 + 45 86 85 surfactant A .sup.a) not according to the invention

(9) TABLE-US-00002 TABLE 1B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Without .sup.a) — 68 10 Amine alkoxylate A .sup.a) 300 86 78 Surfactant A .sup.a) 300 90 71 Amine alkoxylate A + 255 + 45 93 88 surfactant A .sup.a) not according to the invention

(10) TABLE-US-00003 TABLE 1C Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 75 54 Amine alkoxylate A + 350 + 50 86 73 surfactant A .sup.a) not according to the invention

(11) TABLE-US-00004 TABLE 1D Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 83 69 Amine alkoxylate A + 350 + 50 94 94 surfactant A .sup.a) not according to the invention

Example 3

Amine Alkoxylate+Surfactant A+Surfactant B

(12) The experiments were carried out as in Example 2 and the results are compiled in Table 2.

(13) TABLE-US-00005 TABLE 2A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 75 54 Surfactant B .sup.a) 100 63 39 Amine alkoxylate A + 250 + 50 + 100 81 61 surfactant A + surfactant B .sup.a) not according to the invention

(14) TABLE-US-00006 TABLE 2B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 83 69 Surfactant B .sup.a) 100 73 50 Amine alkoxylate A + 250 + 50 + 100 95 83 surfactant A + surfactant B .sup.a) not according to the invention

Example 4

Amine Alkoxylate+Surfactant A+Surfactant C

(15) The experiments were carried out as in Example 2 and the results are compiled in Table 3.

(16) TABLE-US-00007 TABLE 3A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 75 54 Surfactant C .sup.a) 100 61 36 Amine alkoxylate A + 250 + 50 + 100 90 78 surfactant A + surfactant C .sup.a) not according to the invention

(17) TABLE-US-00008 TABLE 3B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 83 69 Surfactant C .sup.a) 100 68 39 Amine alkoxylate A + 250 + 50 + 100 93 84 surfactant A + surfactant C .sup.a) not according to the invention

Example 5

Amine Alkoxylate+Surfactant A+Surfactant D

(18) The experiments were carried out as in Example 2 and the results are compiled in Table 4.

(19) TABLE-US-00009 TABLE 4A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 85 62 Surfactant D .sup.a) 300 80 51 Amine alkoxylate A + 200 + 50 + 50 88 75 surfactant A + surfactant D .sup.a) not according to the invention

(20) TABLE-US-00010 TABLE 4B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 86 78 Surfactant D .sup.a) 300 85 63 Amine alkoxylate A + 200 + 50 + 50 91 85 surfactant A + surfactant D .sup.a) not according to the invention

Example 6

Amine Alkoxylate+Surfactant A+Surfactant E

(21) The experiments were carried out as in Example 2 and the results are compiled in Table 5.

(22) TABLE-US-00011 TABLE 5A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 85 62 Surfactant E .sup.a) 300 78 53 Amine alkoxylate A + 200 + 50 + 50 89 81 surfactant A + surfactant E .sup.a) not according to the invention

(23) TABLE-US-00012 TABLE 5B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 86 78 Surfactant E .sup.a) 300 81 76 Amine alkoxylate A + 200 + 50 + 50 90 83 surfactant A + surfactant E .sup.a) not according to the invention

Example 7

Amine Alkoxylate+Surfactant E+Surfactant F

(24) The experiments were carried out as in Example 2 and the results are compiled in Table 6.

(25) TABLE-US-00013 TABLE 6A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 85 62 Surfactant E .sup.a) 300 78 53 Surfactant F .sup.a) 300 72 59 Amine alkoxylate A + 200 + 50 + 50 85 80 surfactant E + surfactant F .sup.a) not according to the invention

(26) TABLE-US-00014 TABLE 6B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 300 86 78 Surfactant E .sup.a) 300 81 76 Surfactant F .sup.a) 300 81 80 Amine alkoxylate A + 200 + 50 + 50 89 92 surfactant E + surfactant F .sup.a) not according to the invention

Example 8

Amine Alkoxylate+Surfactant A+Surfactant G

(27) The experiments were carried out as in Example 2 and the results are compiled in Table 7.

(28) TABLE-US-00015 TABLE 7A Efficacy after 21 days at 140 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 75 54 Amine alkoxylate A + 250 + 50 + 100 83 65 surfactant A + surfactant G .sup.a) not according to the invention

(29) TABLE-US-00016 TABLE 7B Efficacy after 21 days at 280 g/ha glyphosate Winter wheat Soybean Amount efficacy efficacy Amine alkoxylate/surfactant [g/ha] [%] [%] Amine alkoxylate A .sup.a) 400 83 69 Amine alkoxylate A + 250 + 50 + 100 90 85 surfactant A + surfactant G .sup.a) not according to the invention

Example 9

Stability Test

(30) An aqueous solution composed of 480 g/l glyphosate isopropylamine salt, 225 g/l amine alkoxylate A and 75 g/l surfactant H was stored for four weeks, either at −5° C. or +55° C. No phase separation occurred.

(31) By way of comparison, an aqueous solution composed of 480 g/l of glyphosate isopropylamine salt and 300 g/l of Genamine® T 150 (C.sub.16/18-amine ethoxylate having 15 EO units, commercially available from Clariant) was stored correspondingly. A clear phase separation into an aqueous bottom phase with glyphosate salt and a top phase with Genamine® T150 occurred.

(32) By way of further comparison, an aqueous solution composed of 480 g/l of glyphosate isopropylamine salt, 150 g/l of Genamine® T 150 and 150 g/l surfactant H was stored correspondingly. Likewise, a clear phase separation into an aqueous bottom phase with glyphosate salt and a top phase with Genamine® T150 occurred.