Agrochemical oil compositions comprising alkylpolysiloxane adjuvants of high silicone character

Patent metadata

Field	Value
Publication number	US-9706771-B2
Application number	US-200913124522-A
Country	US
Kind code	B2
Filing date	Sep 3, 2009
Priority date	Oct 17, 2008
Publication date	Jul 18, 2017
Grant date	Jul 18, 2017

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.

First claim

What is claimed is:

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 o

Assignees

• Poffenberger Craig
• Lindsay David
• Simpelkamp Jörg
• Hartung Christian
• Ferenz Michael
• Evonik Degussa Gmbh

Inventors

• Poffenberger Craig
• Lindsay David
• Simpelkamp Jörg
• Hartung Christian
• Ferenz Michael

Classifications

• B01F17/0071

  Operations & Transport · mapped topic

• A01N43/84

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4 · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title

• A01N25/30 Primary

  characterised by the surfactants · CPC title

• A01N47/14

  Di-thio analogues thereof · CPC title