Novel surfactants and formulations

Abstract

A herbicidal composition is provided comprising an aqueous solution of N-phosphonomethylglycine, predominantly in the form of the potassium salt thereof, at a concentration of at least 300 g a.e./l of the composition; and a surfactant component in solution or stable suspension, emulsion, or dispersion in the water, comprising one or more surfactants in a total amount of about 20 to about 300 g/l of the composition, wherein the composition has a viscosity of less than about 250 centipoise at 0° C. or a Gardner color value less than 10.

1 . A storage-stable herbicidal concentrate which may be diluted with water to provide an aqueous herbicidal application mixture for application to the foliage of a plant, said concentrate comprising glyphosate or a salt or ester thereof in a concentration of at least about 500 g a.e./l glyphosate acid equivalent, and a surfactant component, the nature and concentration of said surfactant component in said concentrate being such that, upon applying said application mixture to the foliage of a plant, anisotropic aggregates comprising said surfactant are formed on said plant foliage.  
   
   
       2 . A concentrate as set forth in  claim 1  which is substantially devoid of liquid crystals comprising said surfactant but having a composition such that, upon application to a plant of said concentrate or said application mixture, liquid crystals comprising said surfactant are formed in or on said plant foliage.  
   
   
       3 . A concentrate as set forth in  claim 1  wherein the nature and concentration of said surfactant component in said concentrate being such that, upon applying said application mixture to the foliage of a plant, liquid crystals comprising said surfactant are formed on the plant foliage.  
   
   
       4 . A concentrate as set forth in  claim 1  wherein the concentrate comprises a salt of glyphosate selected from the group consisting of a potassium, monoammonium, diammonium, sodium, monoethanolamine, dimethylammonium, dimethylamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine, sulfoxonium or trimethylsulfonium salt of glyphosate and mixtures thereof.  
   
   
       5 . A concentrate as set forth in  claim 3  containing said surfactant in a weight ratio to glyphosate acid equivalent of at least about 0.05.  
   
   
       6 . A concentrate as set forth in  claim 3  containing said surfactant in a weight ratio to glyphosate acid equivalent between about 0.05 and about 0.33.  
   
   
       7 . A concentrate as set forth in  claim 1  wherein anisotropic aggregates are formed in said plant foliage upon application to said foliage of said application mixture and evaporation of water from the application mixture on said foliage.  
   
   
       8 . A concentrate as set forth in  claim 1  wherein the concentrate comprises potassium glyphosate.  
   
   
       9 . A concentrate as set forth in  claim 1  wherein the glyphosate concentration is from about 500 g a.e./L to about 600 g a.e./L.  
   
   
       10 . A concentrate as set forth in  claim 1  wherein the concentrate has a cloud point of at least about 50° C. and a crystallization point of not higher than about 0° C.  
   
   
       11 . A concentrate as set forth in  claim 1  wherein the concentrate has a density of at least about 1.210 grams/liter.  
   
   
       12 . A concentrate as set forth in  claim 1  wherein the surfactant comprised by the concentrate is not substantially antagonistic to the herbicidal activity of the glyphosate.  
   
   
       13 . A concentrate as set forth in  claim 10  wherein the concentrate has a cloud point of at least about 60° C. and a crystallization point of not higher than about −10° C.  
   
   
       14 . A concentrate as set forth in  claim 1  wherein the concentrate has a viscosity of less than about 1000 c.p. at 0° C. at 45/s shear rate.  
   
   
       15 . A concentrate as set forth in  claim 14  wherein the concentrate has a viscosity of less than about 250 c.p. at 0C. at 45/s shear rate.  
   
   
       16 . A storage stable herbicidal liquid concentrate which may be diluted with water to provide an aqueous herbicidal application mixture for application to the foliage of a plant, said concentrate comprising a potassium, monoammonium, diammonium, sodium, monoethanolamine, dimethylammonium, dimethylamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine, sulfoxonium or trimethylsulfonium salt of glyphosate and having a glyphosate acid equivalent concentration of at least 270 grams per liter, the nature of said surfactant and the composition of said concentrate being such that, upon application to a plant of the concentrate or said application mixture, anisotropic aggregates comprising said surfactant are formed on said plant foliage.  
   
   
       17 . A concentrate as set forth in  claim 16  wherein the nature and concentration of said surfactant component in said concentrate are such that, upon applying said application mixture to the foliage of a plant, liquid crystals comprising said surfactant are formed within the cuticles of the plant foliage.  
   
   
       18 . A concentrate as set forth in  claim 16  wherein the glyphosate concentration is from about 400 g a.e./L to about 600 g a.e./L.  
   
   
       19 . A concentrate as set forth in  claim 16  wherein the concentrate has a cloud point of at least about 50° C. and a crystallization point of not higher than about 0° C.  
   
   
       20 . A concentrate as set forth in  claim 19  wherein the concentrate has a cloud point of at least about 60° C. and a crystallization point of not higher than about −10° C.  
   
   
       21 . A concentrate as set forth in  claim 16  wherein the concentrate has a viscosity of less than about 1000 c.p. at 0° C. at 45/s shear rate.  
   
   
       22 . A concentrate as set forth in  claim 21  wherein the concentrate has a viscosity of less than about 250 c.p. at 0° C. at 45/s shear rate.  
   
   
       23 . A concentrate as set forth in  claim 16  wherein the concentrate has a density of at least about 1.210 grams/liter.  
   
   
       24 . A concentrate as set forth in  claim 16  wherein the surfactant comprised by the concentrate is not substantially antagonistic to the herbicidal activity of the glyphosate.  
   
   
       25 . A concentrate as set forth in  claim 1  or  claim 16  wherein the surfactant is selected from the group consisting of:  
     
       
         
         
             
             
         
       
     
     wherein R 1  is hydrogen or hydrocarbyl or substituted hydrocarbyl having at least 7 carbon atoms; R 2  in each of the (R 2 O) x  and (R 2 O) y  groups is independently C 2 -C 4  alkylene; R 3 is a hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; R 4  and R 5  are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, —(R 6 ) n —(R 2 O) y R 7 , or R 4  and R 5 , together with the nitrogen atom to which they are attached, form a cyclic or heterocyclic ring; R 6  is hydrocarbylene or substituted hydrocarbylene containing from 1 to about 6 carbon atoms, R 7  is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms, n is 0 or 1, and x and y are independently an average number from 1 to about 60, provided, however, that when R 2  and R 3  in each of the (R 2 O) x  groups is ethylene, R 1  is other than unsubstituted alkyl or R 4 is other than hydrogen or unsubstituted alkyl when R 5 is hydrogen or unsubstituted alkyl, and when R 2  and R 3  are isopropylene and x is 1, R 1  is other than unsubstituted alkyl or R 4 is other than —(R 2 O) y R 7 ; 
 (b) alkoxylated poly(hydroxyalkyl)amines having the formula:  
                     
 wherein R 1  and R 3  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R 2  in each of the (R 2 O), groups is independently C 2 -C 4  alkylene; R 4 is hydrocarbylene or substituted hydrocarbylene having from 1 to about 30 carbon atoms, R 5  is hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl; x is an average number from 0 to about 30, and y is 0 or 1;  
 (c) di-poly(hydroxyalkyl)amines having the formula:  
                     
 wherein R 1  and R 3  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R 2  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R 4  and R 5  are independently hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl, provided, however, that when R 1  and R 3  are methyl, R 2  is other than octylene;  
 (d) alkoxylated triamines having the formula:  
                     
 wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 2 , R 3 , R 4  and R 5  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 8 )s (R 7 —O) n R 6 ; R 6  is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms; R 7  in each of the (R 7 O) n  groups is independently C 2 -C 4  alkylene; R 8  is hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; n is an average number from 1 to about 10; s is 0 or 1; and x and y are independently an integer from 1 to about 4; provided, however, that when R 1  is alkyl, R 2  is other than hydrogen, x is 3 or 4, or R 4  is other than —(R 7 —O) n R 6 ;  
 (e) monoalkoxylated amines having the formula:  
                     
 wherein R 1  is a hydrocarbyl or substituted hydrocarbyl group having from 1 to about 30 carbon atoms, R 2  is C 2 -C 4  alkylene, R 3 is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R 4  is a linear or branched alkynyl, aryl, or aralkyl group having from 1 to about 30 carbon atoms, and x is an average number from 1 to about 60;  
 (f) amine oxides having the formula:  
                     
 wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from about 8 to about 30 carbon atoms, R 2  and R 3  are independently —(R 4 O) x R 5 , R 4  in each of the (R 4 O) x  groups is independently C 2 -C 4  alkylene, R 5  is hydrogen, or a hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, x is an average number from 1 to about 50.  
 (g) an alkoxylated amine oxide having the formula:  
                     
 wherein R 1  is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 2  in each of the (R 2 O) x  and (R 2 O) y  groups is independently C 2 -C 4  alkylene; R 3  is a hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; R 4  and R 5  are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, —(R 6 ) n —(R 2 O) y R 7 ; R 6  is hydrocarbylene or substituted hydrocarbylene containing from 1 to about 6 carbon atoms, R 7  is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms, n is 0 or 1, and x and y are independently an average number from 1 to about 60;  
 (h) alkoxylated diamines having the formula:  
                     
 wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from about 8 to about 30 carbon atoms; R 2  in each of the (R 2  O) x  groups and the (R 2 O) y  groups is independently C 2 -C 4  alkylene; R 3 , R 5  and R 6  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 2 O) y R 7 ; R 4 is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms, —C(═NR 12 )—, —C(S)—, or —C(O)—; R 7 is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms; R 11 , R 12  and R 13  are hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; x is an average number from 1 to about 30; and y is an average number from 1 to about 50, provided, however, that at least one of R 3 , R 5  and R 6  is —(R 2 O) y R 7 , at least one R 2  is other than ethylene, R 4  is other than unsubstituted propylene, R 1  is other than unsubstituted alkyl, or x is from 2 to about 30;  
 (i) dialkoxylated amines having the formula:  
                     
 wherein R 1  is a hydrocarbyl or substituted hydrocarbyl having from about 6 to about 30 carbon atoms, or —R 4 SR 5 , R 4  and R 2  in each of the (R 2 O) x  and the (R 2 O) y  groups is independently C 2 -C 4  alkylene, R 3  is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R 5  is a linear or branched alkyl group having from about 4 to about 15 carbon atoms, and x and y are independently an average number from 1 to about 40;  
 (j)dialkoxylated alcohols having the formula:  
                     
 wherein R 1  is independently hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R 2  in each of the (R 2 O) x  and the (R 2 O) y  groups is independently C 2 -C 4  alkylene, R 3  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, and x and y are independently an average number from 1 to about 60; and  
 (k) compounds of the formula:  
                     
 wherein R 1 , R 9 , and R 12  are independently hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 2 O) p R 13 ; R 2  in each of the (R 2 O) m , (R 2 O) n , (R 2 O) p  and (R 2 O) q  groups is independently C 2 -C 4  alkylene; R 3 , R 8 , R 11 , R 13  and R 15  are independently hydrogen, or a hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 4  is —(CH 2 ) y OR 13  or —(CH 2 ) y O(R 2 O) q R 3 ; R 5 , R 6  and R 7  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or R 4 ; R 10  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R 14  is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(CH 2 ) z O(R 2 O) p R 3 ; m, n, p and q are independently an average number from 1 to about 50; X is —O—, —N(R 14 )—, —C(O)—, —C(O)O—, —OC(O)—, —N(R 15 )C(O)—, —C(O)N(R 15 )—, —S—, —SO—, or —SO 2 —; t is 0 or 1; A-is an agriculturally acceptable anion; and y and z are independently an integer from 0 to about 30.  
 
   
   
       26 . A concentrate as set forth in  claim 1  or  claim 16  wherein the surfactant is selected from the group consisting of: 
 (a) aminated alkoxylated alcohol having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl containing at least 7 carbon atoms; R 2  in each of the (R 2 O) x  and (R 2 O) y  groups is independently C 2 -C 4  alkylene; R 3  and R 6  are each independently hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; R 4  is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy substituted hydrocarbyl, —(R 6 ) n —(R 2 O) y R 7 , —C(═NR 11 )NR 12 R 13 , —C(═O)NR 12 R 13 , —C(═S)NR 12 R 13  or together with R 5  and the nitrogen atom to which they are attached, form a cyclic or heterocyclic ring; R 5  is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy substituted hydrocarbyl, —(R 6 ) n —(R 2 O) y R 7 , —C(═NR 11 )NR 12 R 13 , —C(═O)NR 12 R 13 , —C(═S)NR 12 R 13 , or together with R 4  and the nitrogen atom to which they are attached, form a cyclic or heterocyclic ring; R 7  is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms; R 11 , R 12  and R 13  are hydrogen, hydrocarbyl or substituted hydrocarbyl, R 14  is hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy substituted hydrocarbyl, —(R 6 ) n —(R 2 O) y R 7 , —C(═NR 11 )NR 12 R 13 , —C(═O)NR 12 R 13 , or —C(═S)NR 12 R 13 , n is 0 or 1, x and y are independently an average number from 1 to about 60, and A- is an agriculturally acceptable anion, provided, however, that when R 2  and R 3  are isopropylene and x is 1, R 1  is other than alkyl or R 4  is other than —(R 2 O) y R 7 ;    (b) hydroxylated amines having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from about 4 to about 30 carbon atoms, R 2  is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, and R 3 is hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl;    (c) diamines having the formula:                          wherein R 1 , R 2  and R 5  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms or —R 8 (OR 9 ) n OR 10 , R 3  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R 8  and R 9  are individually hydrocarbylene or substituted hydrocarbylene having from 2 to about 4 carbon atoms, R 4  and R 10  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an average number from 0 to about 40, X is —C(O)— or —SO 2 —, and A- is an agriculturally acceptable anion;    (d) mono- or di-ammonium salts having the formula:                          wherein R 1 , R 2 , R 4 , R 5  and R 7  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms or —R 8 (OR 9 ) n OR 10 , R 6  is hydrocarbyl or substituted hydrocarbyl having from about 1 to about 30 carbon atoms, R 3 is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R 8  and R 9  are individually hydrocarbylene or substituted hydrocarbylene having from 2 to about 4 carbon atoms, R 10  is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an average number from 0 to about 40, X is —C(O)— or —SO 2 —, Z is —C(O)—, and A- is an agriculturally acceptable anion;    (e) poly(hydroxyalkyl)amines having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from about 4 to about 30 carbon atoms or —R 4 OR 5 , R 2 is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R 3 is hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl, R 4  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, and R 5  is hydrogen or hydrocarbyl or substituted hydrocarbyl having from about 1 to about 30 carbon atoms. (f) di-poly(hydroxyalkyl)amine having the formula:                          wherein R 1  and R 3  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R 2  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, and R 4  and R 5  are independently hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl;    (g) quaternary poly(hydroxyalkyl)amine salts having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from about 4 to about 30 carbon atoms, R 2  and R 3  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, and R 4  is hydroxyalkyl, polyhydroxyalkyl, or poly(hydroxyalkyl)alkyl and X −  is an agriculturally acceptable anion;    (h) triamines having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 2 , R 3 , R 4  and R 5  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 8 ) s  (R 7 O) n R 6 ; R 6  is hydrogen or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R 7  in each of the (R 7 O) n  groups is independently C 2 -C 4  alkylene; R 8  is hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms, n is an average number from 1 to about 10, s is 0 or 1, and x and y are independently an integer from 1 to about 4;    and mixtures thereof, wherein the pesticide is other than a bacteriocide if the composition includes a surfactant of group (a) or (d).    
   
   
       27 . A formulation useful in retarding the growth of vegetation comprising an aqueous mixture containing a surfactant and glyphosate or a salt or ester thereof, the nature of said surfactant and the composition of said formulation being such that, upon application of the formulation to a plant, anisotropic aggregates comprising said surfactant are formed on the foliage of the plant wherein the surfactant is selected from the group consisting of: 
 (a) monoalkoxylated amines having the formula:                          wherein R 1  is hydrogen or hydrocarbyl or substituted hydrocarbyl having at least 7carbon atoms; R 2  in each of the (R 2 O) x  and (R 2 O) y  groups is independently C 2 -C 4  alkylene; R 3  is a hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; R 4  and R 5  are each independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, —(R 6 ) n —(R 2 O) y R 7 , or R 4  and R 5 , together with the nitrogen atom to which they are attached, form a cyclic or heterocyclic ring; R 6  is hydrocarbylene or substituted hydrocarbylene containing from 1 to about 6 carbon atoms, R 7  is hydrogen or a linear or branched alkyl group having 1 to about 4 carbon atoms, n is 0 or 1, and x and y are independently an average number from 1 to about 60, provided, however, that when R 2  and R 3  in each of the (R 2 O) x  groups is ethylene, R 1  is other than unsubstituted alkyl or R 4  is other than hydrogen or unsubstituted alkyl when R 5 is hydrogen or unsubstituted alkyl, and when R 2  and R 3  are isopropylene and x is 1, R 1  is other than unsubstituted alkyl or R 4 is other than —(R 2 O) y R 7 ;    (b) di-poly(hydroxyalkyl)amines having the formula:                          wherein R 1  and R 3  are independently hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R 2  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, and m and n are independently integers from 1 to about 8, provided, however, that when R 1  and R 3  are methyl, R 2  is other than octylene;    (c) alkoxylated triamines having the formula:                          wherein R 1  is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 2 , R 3 , R 4  and R 5  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 8 )s (R 7 —O) n R 6 ; R 6  is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms; R 7  in each of the (R 7 O) n  groups is independently C 2 -C 4  alkylene; R 8  is hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; n is an average number from 1 to about 10; s is 0 or 1; and x and y are independently an integer from 1 to about 4; provided, however, that when R 1  is alkyl, R 2  is other than hydrogen, x is 3 or 4, or R 4  is other than —(R 7 —O) n R 6 ;    (d) monoalkoxylated amines having the formula:                          wherein R 1  is a hydrocarbyl or substituted hydrocarbyl group having from 1 to about 30 carbon atoms, R 2  is C 2 -C 4  alkylene, R 3  is hydrogen, or a linear or branched alkyl group having from 1 to about 4 carbon atoms, R 4  is a linear or branched alkynyl, aryl, or aralkyl group having from 1 to about 30 carbon atoms, and x is an average number from 1 to about 60; and    (e) compounds of the formula:                          wherein R 1 , R 9 , and R 12  are independently hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(R 2 O) p R 13 ; R 2  in each of the (R 2 O) m , n (R 2 O), (R 2 O) p  and (R 2 O) q  groups is independently C 2 -C 4  alkylene; R 3 , R 8 , R 11 , R 13  and R 15  are independently hydrogen, or a hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R 4  is —(CH 2 ) y OR 13  or —(CH 2 ) y O(R 2 O) q R 3 ; R 5 , R 6  and R 7  are independently hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or R 4 ; R 1  is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R 14  is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —(CH 2 ) z O(R 2 O) p R 3 ; m, n, p and q are independently an average number from 1 to about 50; X is —O—, —N(R 14 )—, —C(O)—, —C(O)O—, —OC(O)—, —N(R 15 )C(O)—, —C(O)N(R 15 )—, —S—, —SO—, or —SO 2 —; t is or 1; A- is an agriculturally acceptable anion; and y and z are independently an integer from 0 to about 30.    
   
   
       28 . A formulation as set forth in  claim 27  wherein the nature of said surfactant and the composition of said formulation are such that, upon application of the formulation to a plant, liquid crystals comprising said surfactant are formed in the foliage of said plant.  
   
   
       29 . A formulation as set forth in  claim 27  wherein the nature of said surfactant and the composition of said formulation are such that, upon application of the formulation to a plant, liquid crystals comprising said surfactant form transcuticular hydrophilic channels through the cuticle of said plant.  
   
   
       30 . A formulation as set forth in  claim 27  wherein the nature of said surfactant and the composition of said formulation are such that, upon application of the formulation to a plant, liquid crystals comprising said surfactant are formed on the foliage of said plant irrespective of the presence or absence of another surfactant.  
   
   
       31 . A formulation as set forth in  claim 30  wherein the nature of said surfactant and the composition of said formulation are such that, upon application of the formulation to a plant, liquid crystals comprising said surfactant are formed in the foliage of said plant irrespective of the presence or absence of another surfactant.  
   
   
       32 . A formulation as set forth in  claim 31  wherein the liquid crystals comprise a stratified array of the surfactant molecules wherein the hydrophilic moieties of the surfactant molecules in one stratum of the stratified array is oriented toward the hydrophilic moieties of the surfactant molecules in a second stratum of the stratified array and an aqueous liquid may migrate within said liquid crystal in a hydrophilic region within which said hydrophilic moieties of said one stratum and said second stratum are disposed.  
   
   
       33 . A formulation as set forth in  claim 32  wherein cationic moieties of surfactant molecules of said one stratum are in contact with a hydrophobic surface on said foliage or within a cuticle of said plant.  
   
   
       34 . A formulation as set forth in  claim 32  wherein said hydrophilic region comprises a channel for penetration of glyphosate into cuticles of said plant.  
   
   
       35 . A formulation as set forth in  claim 33  wherein said hydrophilic region comprises a channel for uptake and translocation of glyphosate within said plant.  
   
   
       36 . A formulation as set forth in  claim 27  wherein said liquid crystals are lyotropic.  
   
   
       37 . A formulation as set forth in  claim 27  which is substantially devoid of liquid crystals comprising said surfactant but having a composition such that, upon application of the formulation to a plant, liquid crystals comprising said surfactant are formed in an aqueous layer on the surface of foliage of the plant.  
   
   
       38 . A formulation as set forth in  claim 27  wherein the weight ratio of glyphosate to said surfactant is not greater than about 10:1.  
   
   
       39 . A formulation as set forth in  claim 27  containing between about 500 and about 600 grams per liter glyphosate acid equivalent.  
   
   
       40 . A formulation as set forth in  claim 27  wherein said liquid crystals are formed upon evaporation of water from said formulation upon application to said foliage.  
   
   
       41 . A formulation as set forth in  claim 27  wherein the formulation comprises potassium glyphosate.  
   
   
       42 . A formulation as set forth in  claim 27  wherein the glyphosate concentration is from about 400 g a.e./L to about 600 g a.e./L.  
   
   
       43 . A formulation of  claim 27  wherein the formulation has a cloud point of at least about 50° C. and a crystallization point not higher than about 0° C.  
   
   
       44 . A formulation of  claim 42  wherein the formulation has a cloud point of at least about 60° C. and a crystallization point not higher than about −10° C.  
   
   
       45 . A formulation of  claim 27  wherein the formulation has a viscosity of less than about 1000 c.p. at 0° C. at 45/s shear rate.  
   
   
       46 . A formulation of  claim 27  wherein the formulation is a concentrate.  
   
   
       47 . A formulation of  claim 27  wherein the formulation has a density of at least about 1.210 grams/liter.  
   
   
       48 . A formulation of  claim 47  wherein the formulation has a density of at least about 1.215 grams/liter.  
   
   
       49 . A formulation of  claim 48  wherein the formulation has a density of at least about 1.220 grams/liter.  
   
   
       50 . A formulation of  claim 27  wherein the surfactant comprised by the formulation is not substantially antagonistic to the herbicidal activity of the glyphosate.  
   
   
       51 . A formulation of  claim 27  further comprising a second herbicide.  
   
   
       52 . A formulation of  claim 27  wherein the formulation comprises a salt of glyphosate selected from the group consisting of potassium, monoammonium, diammonium, sodium, monoethanolamine, dimethylammonium, dimethylamine, n-propylamine, ethylamine, ethylenediamine, hexamethylenediamine, sulfoxonium or trimethylsulfonium salt of glyphosate and mixtures thereof.  
   
   
       53 . A formulation of  claim 52  wherein the glyphosate is predominantly in the form of the potassium salt.