IP Library Granted Patent US 9,706,771
Granted Patent B2
US 9,706,771 · App. 13/124,522 · Granted Jul 18, 2017

Agrochemical oil compositions comprising alkylpolysiloxane adjuvants of high silicone character

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Quick Facts
Patent No.
US 9,706,771
App. No.
13/124,522
Granted
Jul 18, 2017
Kind
B2
Abstract

The invention relates to agrochemical compositions comprising oils and alkylpolysiloxanes of high silicone character (HSCAS) with good oil compatibility which improve the spreading behavior and reduce surface tension of oil-based agricultural formulations, and optionally comprising agrochemically active ingredients such as fungicides, insecticides or herbicides and/or inert ingredients such as emulsifiers and other agrochemically acceptable components.

Claims (96)

1. An agrochemical oil composition comprising:

(i) one or more alkylpolysiloxanes of high silicone character which have blocks of unmodified polydimethylsiloxane units in their molecular structure, the blocks having on average at least 10 uninterrupted polydimethylsiloxane units (-Me 2 SiO—);

(ii) one or more oils; and

(iii) optionally one or more agrochemically active compounds, emulsifiers and other agrochemically acceptable ingredients;

where the surface tension of the oil is reduced by the high silicon character alkylpolysiloxane at concentrations of only 1 wt. % of alkylpolysiloxane in the oil; and

wherein the one or more alkylpolysiloxanes of high silicone character comprise at least one alkylpolysiloxane selected from the group consisting of:

(1) a siloxane (a) of formula (I):

R″ 3 Si—O—(SiR 2 O) u —(SiRR′O) v —SiR″ 3   (I)

wherein:

R is methyl;

R′ is an aliphatic linear or branched alkyl radical containing 10-24 carbons;

R″ is methyl;

u is 20 to 300; and

v is 2 to 30;

provided that u/v is 10 to 25.

2. The agrochemical oil composition of claim 1 ;

wherein the one or more alkylpolysiloxanes of high silicone character further comprise at least one alkylpolysiloxane selected from the group consisting of:

(2) a siloxane (b) which is obtained by:

performing a reaction (i) comprising reacting an organopolysiloxane of formula (II) with a vinylsiloxane of formula (III) in the presence of Pt or Rh catalysts, provided that the organopolysiloxane (H) is present in at least 6-fold molar excess, of the vinylsiloxane (III), to produce a reaction product (i), wherein:

the formula (II) is:

 wherein:

 R1 is methyl;

 R2 is R1 or H, provided that at least three radicals R2 of the organopolysiloxane of formula (II) are hydrogen;

 a is 10-500;

 b is 1-50;

 c is 0-5; and

the vinylsiloxane of formula (III) is:

 wherein d is 10 to 1000 and R1 is as defined above; and

subsequently performing, with the reaction product (i), one or a combination of reactions (ii) and (iii);

wherein reaction (ii) is a transition metal-catalyzed partial or complete addition of the SiH groups to alkenyl and/or alkynylfunctional compounds; and

wherein reaction (iii) is under utilization of a catalyst, partial or complete conversion of the SiH groups remaining after reactions (i) and (ii) with at least one alcohol selected from the group consisting of linear or branched, saturated mono/polyunsaturated, aromatic, aliphatic/aromatic, potentially halogen-containing monofunctional alcohols, monofunctional polyether alcohols, monofunctional polyester alcohols, and aminoalcohols.

3. The agrochemical composition of claim 1 ;

wherein:

the one or more alkylpolysiloxanes are present in an amount of 0.01 to 99 vol. %;

the one or more oils are present in an amount of 1 to 99.99 vol. %;

the one or more agrochemically active compounds are present in an amount of 0 to 30 vol. %;

the one or more emulsifiers are present in an amount of 0 to 15 vol. %;

water is present in an amount of 0 to 95 vol. %; and

other inert ingredients are present in an amount of 0 to 50 vol. %.

4. The agrochemical composition according of claim 3 ;

wherein:

the one or more alkylpolysiloxanes are present in an amount of 0.1 to 5 vol. %;

the one or more oils are present in an amount of 10 to 60 vol. %;

the one or more agrochemically active compounds are present in an amount of 0.5 to 20 vol. %;

the one or more emulsifiers are present in an amount of 0.1 to 6 vol. %; and

water is present in an amount of 20 to 85 vol. %.

5. The agrochemical composition according of claim 3 ;

wherein:

the one or more alkylpolysiloxanes are present in an amount of 0.1 to 1 vol. %;

the one or more oils comprise one or more of a mineral oil, a vegetable oil, or a methylated vegetable oil present in an amount of 15 to 30 vol. %;

the one or more agrochemically active compounds are present in an amount of 2 to 15 vol. %;

the one or more emulsifiers are present in an amount of 0.1 to 3 vol. %; and

water is present in an amount of 60-80 vol. %.

6. The agrochemical composition of claim 1 ;

wherein the agrochemically active compound is a fungicide, herbicide, or insecticide.

7. The agrochemical composition of claim 1 ;

wherein the oil is a mineral oil, vegetable oil, or methylated vegetable oil.

8. The agrochemical composition of claim 1 ;

wherein:

R′ is a 14-18 carbon alkyl;

u is 50-150; and

v is 3-10.

9. The agrochemical composition of claim 2 ;

wherein the oil is selected from the group consisting of a mineral oil, vegetable oil, and methylated vegetable oil.

10. The agrochemical composition of claim 9 ;

wherein the siloxane (b) is derived by complete conversion of the remaining SiH groups of the reaction product (i) in a transition metal-catalyzed hydrosilylation reaction with monounsaturated linear or branched aliphatic olefins having 8-24 carbon atoms.

11. The agrochemical composition of claim 10 ;

wherein the siloxane (b) is derived by complete conversion of the remaining SiH groups of the reaction product (i) in a transition metal-catalyzed hydrosilylation reaction with monounsaturated linear or branched aliphatic olefins having 16-18 carbon atoms.

12. The agrochemical composition of claim 9 ;

wherein the siloxane (b) is derived by complete conversion of the remaining SiH groups of the reaction product (i) in a transition metal-catalyzed hydrosilylation reaction with a mixture comprising:

at least 80 mol % monounsaturated linear or branched aliphatic olefins having 8-24 carbon atoms; and

up to 20 mol % of alkyl or alkynylfunctional compounds selected from the group consisting of:

unsaturated aromatic hydrocarbons;

unsaturated olefins bearing 1-4 additional substituents selected from the group consisting of hydroxy groups, halogen groups, alkoxy groups, amino groups, alkylamino groups, and ester groups; and

allyl-functional or vinyl-functional polyethers comprised of ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof, with the free end groups selected from the group of saturated alkyloxy, free hydroxy or hydroxy groups esterified with C1-C4 alkanoic acids.

13. The agrochemical composition of claim 9 ;

wherein for the siloxane (b):

R1 is methyl;

a is 10 to 100;

b is 2 to 30;

c is 0; and

d is 30-300.

14. A method of controlling unwanted weeds or treating plants against pests, comprising:

administering a pesticidally effective amount of the agrochemical composition of claim 1 to a plant or weed.

15. A method of controlling unwanted weeds or treating plants against insects or disease, comprising:

administering a herbicidally, insecticidally or disease controlling effective amount of the agrochemical composition of claim 1 to a plant or weed.

16. The method of claim 15 ;

wherein the composition comprises a herbicide, fungicide, or insecticide.

17. The method of claim 15 ;

wherein the treatment is against unwanted fungi which comprises of administering a fungicidal effective amount of the agrochemical composition of claim 1 .

18. The method of claim 17 ;

wherein the plant is banana or plantain.

19. The method of claim 18 ;

wherein the administration of the fungicidal effective amount of the agrochemical composition of claim 1 is on the foliage of the banana or plantain plant.

20. The agrochemical composition of claim 1 ;

wherein the agrochemical oil composition has a surface tension that is at least 15% lower than the one or more oils.

Assignments (3)
MERGER Recorded May 15, 2014
From: EVONIK GOLDSCHMIDT GMBH
To: EVONIK DEGUSSA GMBH
Reel/Frame 032900/0372 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CORRECT SPELLING: POFFENBERGER, CRAIG PREVIOUSLY RECORDED ON REEL 026297 FRAME 0941. ASSIGNOR(S) HEREBY CONFIRMS THE INCORRECT SPELLING: POFFENBERG, CRAIG. Recorded Jul 27, 2011
From: POFFENBERGER, CRAIG
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 026661/0258 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2011
From: POFFENBERG, CRAIG; LINDSAY, DAVID; SIMPELKAMP, JORG; HARTUNG, CHRISTIAN; FERENZ, MICHAEL
To: EVONIK GOLDSCHMIDT GMBH
Reel/Frame 026297/0941 →