Aqueous adjuvant-compositions

Abstract

The invention relates to an aqueous adjuvant composition containing: a) one or more alkyl glucamides of formula (I) wherein R1 is a linear or branched alkyl group with five to nine carbon atoms and R2 is an alkyl group with one to three carbon atoms; b) water; c) optionally a co-solvent. The invention further relates to the use of such compositions to increase the biological activity of pesticides, preferably of herbicides, and to produce an aqueous pesticide composition. ##STR00001##

Claims

1. An aqueous solution of an adjuvant composition comprising a) a mixture of two alkyl-N-glucamides of the formula (I) ##STR00004## in which R1 is a linear or branched alkyl group having 7 or 9 carbon atoms, R2 is an alkyl group having 1 carbon atom, wherein the fraction of the alkyl-N-glucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 10 to 90 wt %, and the fraction of the alkyl-N-glucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 10 to 90 wt %, based on the total amount of alkylglucamides present in the mixture, b) water and c) optionally a cosolvent, with the proviso, that the total amount of component a) is at least 30 wt %, based on the total weight of the composition and with the proviso that no further alkyl-N-glucamide is present in the aqueous solution.

2. The aqueous solution of an adjuvant composition as claimed in claim 1, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 20 to 80 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 20 to 80 wt %, based on the total amount of alkylglucam ides present in the mixture.

3. The aqueous solution of an adjuvant composition as claimed in claim 1, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 30 to 70 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 30 to 70 wt %, based on the total amount of alkylglucam ides present in the mixture.

4. The aqueous solution of an adjuvant composition as claimed in claim 1, wherein the total amount of component a) is between 30 and 90 wt %, based on the total weight of the composition.

5. A method for boosting the biological activity of a pesticide, comprising the step of adding at least one adjuvant composition as claimed in claim 1 to the pesticide.

6. An aqueous solution of an adjuvant composition consisting essentially of a) a mixture of two alkylglucam ides of the formula (I) ##STR00005## in which R1 is a linear or branched alkyl group having 7 or 9 carbon atoms, R2 is an alkyl group having 1 carbon atom, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 10 to 90 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 10 to 90 wt %, based on the total amount of alkylglucam ides present in the mixture, and b) water, with the proviso, that the total amount of component a) is at least 30 wt %, based on the total weight of the composition.

7. An aqueous solution of an adjuvant composition consisting essentially of a) a mixture of two alkylglucamides ides of the formula (I) ##STR00006## in which R1 is a linear or branched alkyl group having 7 or 9 carbon atoms, R2 is an alkyl group having 1 carbon atom, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 10 to 90 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 10 to 90 wt %, based on the total amount of alkylglucamides present in the mixture, b) water and c) a cosolvent, with the proviso, that the total amount of component a) is at least 30 wt %, based on the total weight of the composition.

8. The aqueous solution of an adjuvant composition as claimed in claim 6, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 20 to 80 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 20 to 80 wt %, based on the total amount of alkylglucamides present in the mixture.

9. The aqueous solution of an adjuvant composition as claimed in claim 6, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 30 to 70 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 30 to 70 wt %, based on the total amount of alkylglucamides present in the mixture.

10. The aqueous solution of an adjuvant composition as claimed in claim 6, wherein the total amount of component a) is between 30 and 90 wt %, based on the total weight of the composition.

11. The aqueous solution of an adjuvant composition as claimed in claim 7, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 20 to 80 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 20 to 80 wt %, based on the total amount of alkylglucamides present in the mixture.

12. The aqueous solution of an adjuvant composition as claimed in claim 7, wherein the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 7 carbon atoms, is 30 to 70 wt %, and the fraction of the alkylglucamide wherein R1 is a linear or branched alkyl group having 9 carbon atoms, is 30 to 70 wt %, based on the total amount of alkylglucamides present in the mixture.

13. The aqueous solution of an adjuvant composition as claimed in claim 7, wherein the total amount of component a) is between 30 and 90 wt %, based on the total weight of the composition.

Description

WORKING EXAMPLES

(1) The invention is illustrated further below for the skilled person, using examples which, however, should not be considered in any way as confining the invention to the embodiments shown.

Example 1: Production of an Inventive Aqueous Alkylglucamide Composition

(2) The alkylglucamide was prepared from a commercially available C.sub.8/C.sub.10 carboxylic acid methyl ester (C.sub.8 fraction 55 wt %, C.sub.10 fraction 45 wt %) by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. A mixture was formed which as well as 90 wt % of the alkylglucamide of the formula (I) R1=C.sub.8H.sub.17 and C.sub.10H.sub.21, R2=CH.sub.3, also contained 10 wt % of propylene glycol from the reaction mixture. 60 g of this mixture were dissolved in 40 g of water. This gave a stable aqueous solution of the C8/10-N-methylglucamide with a content of 54 wt % in water/propylene glycol.

Example 2: Attempted Production of a Non-Inventive Aqueous Alkylglucamide Composition (Comparative Example)

(3) The alkylglucamide was prepared from a commercially available C.sub.12/C.sub.14 carboxylic acid methyl ester (C.sub.12 fraction 69 wt %, C.sub.14 fraction 25 wt %, other chain constituents 6 wt %) by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This gave a mixture which as well as 90 wt % of the alkylglucamide of the formula (I) R1=C.sub.12H.sub.23 and C.sub.14H.sub.29, R2=CH.sub.3, also contained 10 wt % of propylene glycol from the reaction mixture. An attempt was made to dissolve this mixture in water, in analogy to example 1, but no stable solutions were obtained. The results are compiled in Table 1.

Example 3: Attempted Production of a Non-Inventive Aqueous Alkylglucamide Composition (Comparative Example)

(4) The alkylglucamide was prepared from a commercially available C.sub.16/C.sub.18 carboxylic acid methyl ester (C.sub.16 fraction 38 wt %, C.sub.18 fraction 60 wt %, other chain constituents 2 wt %) by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This gave a mixture which as well as 90 wt % of the alkylglucamide of the formula (I) R1=C.sub.16H.sub.33 and C.sub.18H.sub.37, R2=CH.sub.3, also contained 10 wt % of propylene glycol from the reaction mixture. An attempt was made to dissolve this mixture in water, in analogy to example 1, but no stable solutions were obtained. The results are compiled in Table 1.

(5) TABLE-US-00001 TABLE 1 Dissolution tests of the relatively long-chain alkylglucamides in water Example 2 Example 3 Fraction of C.sub.12/14 Fraction of C.sub.16/18 glucamide in glucamide in wt % wt % in water in water Observations 60 Not soluble 20 Soluble with heating, forms firm gel on cooling 10 Soluble with heating, forms firm gel on cooling 60 Not soluble 20 Soluble with heating, forms firm gel on cooling 10 Soluble with heating, forms firm gel on cooling

(6) Since it was not possible to produce stable and manageable solutions of the C.sub.12/14 glucamide, a 20 wt % strength solution in propylene glycol was prepared for the biological tests and the formulation experiments. With the C.sub.16/18 glucamide, preparing a propylene glycol solution in the same concentration was not possible.

Example 4: Biological Activity of the Adjuvant Compositions

(7) For the purpose of determining the biological activity, greenhouse trials were carried out with glyphosate on Echinochloa crus-galli (L.) Beauv. (ECHCG), Cirsium arvense L. (CIRAR), and Solanum nigrum L. (SOLNI). The plants were cultivated in a greenhouse under 14 hours of irradiation with light at a temperature of 19/14 (0.5) C. (day/night) and a relative humidity of 70/80 (5)% (day/night). The light was supplied via high-pressure sodium lamps, high-pressure mercury lamps, and fluorescent tubes, producing a power of 70 W/m.sup.2 at the leaf level. The plants were grown in 12 cm diameter plastic pots filled with a mixture of sand and humus in a sand:humus ratio of 1:2 by volume.

(8) The pots were placed on an under-soil watering mat, which was wetted daily with a medium-strength nutrient solution. Following their appearance at the substrate surface, seedlings were thinned out to five (ECHCG), two (CIRAR), or one (SOLNI) plant per pot for the activity tests.

(9) The spray solutions were applied using a laboratory sprayer operated with compressed air and fitted with a Teejet TP8003E nozzle at an application rate of 200 l/ha to the plants at 303 kPa. ECHCG was treated at the two- to three-leaf stage; CIRAR and SOLNI were treated at the four-leaf stage.

(10) For the more differentiated examination of the adjuvant effect, the glyphosate active ingredient was underdosed, meaning that the plants are not completely killed. This was done using aqueous solutions of glyphosate-isopropylammonium salt (glyphosate IPA). The amount of glyphosate used was 33.8 g a.e./ha glyphosate IPA (corresponding to 1.0 mmol or 0.17 g a.e./l for a liquid volume of 2001 l/ha) in the case of ECHCG, and at 20.3 g a.e./ha glyphosate IPA (corresponding to 0.6 mmol or 0.10 g a.e./l at a liquid volume of 200 l/ha) for CIRAR and SOLNI.

(11) The amount of adjuvant in each of the spray solutions was 0.25 wt %. The differences in the active contents of the products employed were taken into account. The amounts used were correctedthat is, the figure of 0.25 wt % referred in all cases to 100% active content of the adjuvantsand are therefore comparable with one another.

(12) An overview of the alkylglucamides and comparison substances tested is given below in Table 2.

(13) TABLE-US-00002 TABLE 2 Overview of adjuvants A1 to A4 used Adjuvant Composition A1 (inventive) C.sub.8/C.sub.10-alkyl-N-methylglucamide from example 1, 54 wt % strength solution in water/propylene glycol A2 (comparative) C.sub.12/C.sub.14-alkyl-N-methylglucamide from example 2, 20 wt % strength solution in propylene glycol A3 (comparative) Genamin 267 (tallow fatty amine ethoxylate with 15 mol EO; product of Clariant), 70 wt % strength solution in glycols A4 (comparative) Synergen GL 5 (copolymer consisting of glycerol, coconut fatty acid, and phthalic acid; product of Clariant), 70 wt % strength solution in water

(14) The activity of the various adjuvants was assessed 14 days after application, by determining the mass of the plant parts still present (fresh weight; FW), and was reported as a percentage fraction, relative to the untreated plant (Table 3).

(15) TABLE-US-00003 TABLE 3 Effect of adjuvants on activity of glyphosate IPA FW in % FW in % FW in % (ECHCG) (CIRAR) (SOLNI) Untreated plant 100 100 100 Glyphosate IPA 74.3 95.9 84.5 without adjuvant Glyphosate + A1 1.5 31.9 19.2 Glyphosate + A2 42.9 62.2 29.7 Glyphosate + A3 3.2 14.4 8.7 Glyphosate + A4 4.0 33.0 40.9

(16) The result of the experiments shows that the inventive adjuvant composition based on the C.sub.8/C.sub.10-alkyl-N-methylglucamide (see A1) is much more effective than that based on the longer-chain, non-inventive C.sub.12/C.sub.14-alkyl-N-methylglucamide (see A2). At the same time a comparable (or higher) activity is achieved than with the commercial products Genamin 267 (see A3) or Synergen GL 5 (see A4).

Example 5: Aqueous Glyphosate Compositions

(17) Two inventive pesticide compositions were produced from a commercial aqueous solution of glyphosate-isopropylammonium salt (62 wt % strength in water), the adjuvant composition A1, and water. The resulting compositions I1 and I2 contain 360 and 480 g/l glyphosate a.e. (a.e.: acid equivalent).

(18) For comparison, two non-inventive pesticide compositions were produced with the C.sub.12/C.sub.14-alkyl-N-methylglucamide (A2) and also Genamin 267 (A3) and Synergen GL 5 (A4). The cloud point and the viscosity of the compositions were determined.

(19) The cloud point was determined by heating the composition, which was heated until clouding occurred. Thereafter the composition was cooled with stirring and continual temperature monitoring. The temperature at which the clouded solution turns clear again was recorded as the cloud point value.

(20) The results are set out in Tables 4 and 5 below.

(21) TABLE-US-00004 TABLE 4 Glyphosate IPA 360 g/l a.e. formulations Composition I1 C1 (C.sub.8/C.sub.10N- (C.sub.12/C.sub.14N- methyl methyl C2 C3 glucamide, glucamide, (Genamin (Synergen A1) A2) 267, A3) GL 5, A4) Glyphosate IPA 78.4 78.4 78.4 104.4 (62 wt % strength in H.sub.2O) [g] Adjuvant (as is) 12 18 12 12 [g] Adjuvant 6.5 3.8 8.4 8.4 (calculated on 100 wt %) [g] Water [g] 26.6 20.6 26.6 26.6 Cloud point [ C.] >95 87 57 Viscosity at 25 solid 50 53 25 C. [mPa .Math. s]

(22) With the non-inventive C.sub.12/C.sub.14-alkyl-N-methylglucamide (A2) it was not possible to produce a stable glyphosate formulation (experiment C1); only a firm-consistency gel was formed. No attempt was therefore made to produce a glyphosate composition with an even higher loading (experiment C4).

(23) TABLE-US-00005 TABLE 5 Glyphosate IPA 480 g/l a.e. formulations Composition I2 C4 (C.sub.8/C.sub.10N- (C.sub.12/C.sub.14N- methyl methyl C5 C6 glucamide, glucamide, (Genamin (Synergen A1) A2) 267, A3) GL 5, A4) Glyphosate IPA 104.4 104.4 104.4 (62 wt % strength in water) [g] Adjuvant (as is) 12 12 12 [g] Adjuvant 6.5 8.4 8.4 (calculated on 100 wt %) [g] Water [g] 3.6 3.6 3.6 Cloud point [ C.] >95 separates 64 at 25 C. Viscosity at 95 205 25 C. [mPa .Math. s]

(24) The experiments make it clear that the inventive adjuvant composition (=A1) gave both stable 360 g/l a.e. and stable 480 g/l a.e. glyphosate IPA formulations, which are distinguished by more advantageous applications properties, specifically by higher cloud point and hence at the same time a lower viscosity as well, in comparison to the non-inventive C.sub.12/C.sub.14-alkyl-N-methylglucamide (A2) and to the commercial products Genamin 267 (A3) and Synergen GL 5 (A4).

Example 6: Aqueous 2,4-D-DMA Compositions

(25) An inventive pesticide composition was produced from 76.0 g of aqueous 2,4-D-dimethylammonium salt solution (69 wt % strength), 15.0 g of adjuvant composition A1, and 14.5 g of water. The formulation had an active content of 440 g/l a.e. (acid equivalent) based on 2,4-D. The phase stability of the formulation was determined by ascertaining the cloud point and also the low-temperature stability at 0 C. and 10 C. The formulation showed a cloud point of >95 C. and was homogeneous and phase-stable after storage for a duration of 24 hours both at 0 C. and at 10 C.

Example 7: Aqueous Glyphosate/2,4-D Compositions

(26) Inventive combined glyphosate/2,4-D formulations in three (3) different proportions (I3, I4, and I5) were produced from aqueous solutions of glyphosate-isopropylammonium salt (62 wt % strength), 2,4-D-dimethylammonium salt (69 wt % strength), and the adjuvant composition A1 (see Table 6).

(27) Serving for comparison in each case were three non-inventive compositions, containing Genamin 267 (C7, C8, and C9) and Synergen GL 5 (C10, C11, and C12) in place of A1 (Table 6).

(28) TABLE-US-00006 TABLE 6 Combined glyphosate/2,4-D formulations Acid Glypho- 2,4-D Adju- equivalent sate-IPA DMA vant (glypho- (62 wt % (69 wt % Propyl- compo- sate/ strength strength ene Wa- sition Exper- 2,4-D) in water) in water) glycol ter (amount) iment [g/l] [g] [g] [g] [g] [g] I3 300 + 100 35.6 9.5 4.5 6.4 A1 (9.0) I4 200 + 200 23.7 18.9 4.5 8.9 A1 (9.0) I5 100 + 300 11.9 28.6 0 15.5 A1 (9.0) C7 300 + 100 35.6 9.5 5.0 7.9 A3 (7.0) C8 200 + 200 23.7 18.9 5.0 10.4 A3 (7.0) C9 100 + 300 11.9 28.6 0 17.5 A3 (7.0) C10 300 + 100 35.6 9.5 5.0 7.9 A4 (7.0) C11 200 + 200 23.7 18.9 5.0 10.4 A4 (7.0) C12 100 + 300 11.9 28.6 0 17.5 A4 (7.0)

(29) For all formulations, the phase stability was ascertained by determination of the cloud point, and also the low-temperature stability at 0 C. and 10 C. The results are shown in Table 7 below.

(30) TABLE-US-00007 TABLE 7 Cloud points and low-temperature stability of the compositions Experi- Cloud point Appearance Appearance Appearance ment [ C.] at 25 C. at 0 C. at 10 C. I3 >95 homogeneous homogeneous homogeneous I4 >95 homogeneous homogeneous homogeneous I5 >95 homogeneous homogeneous homogeneous C7 not separates separates separates determined C8 not separates separates separates determined C9 >95 homogeneous homogeneous homogeneous C10 >95 homogeneous separates separates C11 >95 homogeneous homogeneous separates C12 >95 homogeneous homogeneous homogeneous

(31) The results of these experiments show that the inventive combined formulations were much more stable over a broader range than similar compositions based on the commercial products Genamin 267 and Synergen GL 5.