PL193095B1

Glyphosate preparations containing etheroamine surfactants

Abstract

Herbicidal compositions are provided comprising glyphosate or a salt thereof and an etheramine surfactant having the representative chemical structure (a), wherein R1 is a straight or branched chain C6 to about C22 alkyl, aryl or alkylaryl group, m is an average number from 1 to about 10, R2 in each of the m (O-R2) groups is independently C1-C4 alkylene, R3 groups are independently C1-C4 alkylene, and x and y are average numbers such that x+y is in the range from 2 to about 60; or (b), wherein R1 is a straight or branched chain C6 to about C22 alkyl, aryl or alkylaryl group, m is an average number from 1 to about 10, R2 in each of the m (O-R2) groups is independently C1-C4 alkylene, R3 groups are independently C1-C4 alkylene, R4 is C1-C4 alkyl, x and y are average numbers such that x+y is in the range from 0 to about 60, and A<-> is an agriculturally acceptable anion; or (c), wherein R1 is a straight or branched chain C6 to about C22 alkyl, aryl or alkylaryl group, m is an average number from 1 to about 10, R2 in each of the m (O-R2) groups is independently C1-C4 alkylene, R3 groups are independently C1-C4 alkylene, and x and y are average numbers such that x+y is in the range from 2 to about 60.

Term

Term ended

Expired 28 March 2016, 10.5 years ago.

94 claims: 33 independent, 61 dependent

1
Patent claims Zastrzeżenia patentowe 1. A herbicidal composition characterized in that it comprises 1. Kompozycja chwastobójcza, znamienna tym, że zawiera a) a herbicidally effective amount of glyphosate or a salt thereof;and a) skuteczną chwastobójczo ilość glifozatu albo jego soli;i b) an effective herbicidal activity-promoting amount of a surfactant having the chemical structure (i) (R3-ABOUT)x-H b) skutecznie wzmagającą aktywność chwastobójczą ilość środka powierzchniowo-czynnego mającego strukturę chemiczną (i) (R3-O)x-H RHO-RJ— n (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60, or the chemical structure (ii) (R3-ABOUT)x-H RHO-RJ— n (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby takie, że x+y wynosi od 2 do 60 albo strukturę chemiczną (ii) (R3-O)x-H RHO-RJ— n-R4 a (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, R4 oznacza grupę C1-C4 alkilową, x i y oznaczają przeciętne liczby takie, że x+y wynosi od 0 do 60, zaś A- oznacza anion dopuszczalny rolniczo, albo strukturę chemiczną (iii) (R3-O)x-H r,-(0-r2)-n-*0 (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby, że x+y wynosi od 2 do 60. RHO-RJ— nR4 a (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups independently represent C1-C4-alkylene groups, R4 is a C1-C4 alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A- is an agriculturally acceptable anion or chemical structure (iii) (R.3-ABOUT)x-H r, - (0-r2) -n- * 0 (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers with x + y from 2 to 60. PL 193 095 B1 PL 193 095 B1
21
The composition according to p. 16, 17 or 18, characterized in that it contains an alkanolamine salt. 21. Kompozycja według zastrz. 16, albo 17, albo 18, znamienna tym, że zawiera sól alkanoloaminową.
34
The composition according to p. 31, 32 or 33 which comprises a surfactant with a chemical structure in which m is 1. 34. Kompozycja według zastrz. 31, albo 32, albo 33, znamienna tym, że zawiera środek powierzchniowo-czynny o strukturze chemicznej, w której m oznacza 1.
40
The composition according to p. 37, 38 or 39 wherein the surfactant has a chemical structure in which R2 is a linear propylene group and m is 1. 40. Kompozycja według zastrz. 37, albo 38, albo 39, znamienna tym, że zawiera środek powierzchniowo-czynny o strukturze chemicznej, w której R2 oznacza liniową grupę propylenową, a m oznacza 1.
45
The composition according to p. 43 or 44 comprising (a) glyphosate in the form of its isopropylamine salt at a concentration of 480 g ae / L;b) a surfactant with a chemical structure in which R1 is a straight or branched alkyl group from 10 to 15 carbon atoms, R2 is an isopropylene or ethylene group, and x + y is an average number from 2 to 5;(c) the above surfactant is about 80% by weight of the total surfactant present (d) additionally contains about 20% by weight of the total surfactant present e) the total surfactant concentration is 80 g / l. 45. Kompozycja według zastrz. 43 albo 44, znamienna tym, że zawiera (a) glifozat w postaci jego soli izopropyloaminowej o stężeniu od 480 g a.e./l;b) środek powierzchniowo-czynny o strukturze chemicznej, w której R1 oznacza prostą lub rozgałęzioną grupę alkilową od 10 do 15 atomów węgla, R2 oznacza grupę izopropylenową lub etylenową, a x+y oznacza przeciętną liczbę od 2 do 5;(c) powyższy środek powierzchniowo-czynny stanowi około 80% wagowych obecnego środka powierzchniowo-czynnego ogółem (d) dodatkowo zawiera niejonowy środek powierzchniowo-czynny w ilości około 20% wagowych obecnego środka powierzchniowo-czynnego ogółem i e) całkowite stężenie środka powierzchniowo-czynnego wynosi 80 g/l.
46
The composition according to p. 43 or 44 comprising (a) glyphosate in the form of its isopropylamine salt at a concentration of 480 g ae / L;b) a surfactant with a chemical structure in which R1 is a straight or branched alkyl group from 10 to 15 carbon atoms, R2 is a linear propylene group, m is 1, and x + y is an average number from 2 to 5;(c) the above surfactant is about 80% by weight of the total surfactant present, and (d) additionally comprises about 20% by weight of the total surfactant present, and e) the total concentration of surfactant is 80 g / l. 46. Kompozycja według zastrz. 43 lub 44, znamienna tym, że zawiera (a) glifozat w postaci jego soli izopropyloaminowej o stężeniu 480 g a.e./l;b) środek powierzchniowo-czynny o strukturze chemicznej, w której R1 oznacza prostą lub rozgałęzioną grupę alkilową od 10 do 15 atomów węgla, R2 oznacza liniową grupę propylenową, m wynosi 1, a x+y oznacza przeciętną liczbę od 2 do 5;(c) powyższy środek powierzchniowo-czynny stanowi około 80% wagowych obecnego środka powierzchniowo-czynnego ogółem i (d) dodatkowo zawiera niejonowy środek powierzchniowo-czynny w ilości około 20% wagowych obecnego środka powierzchniowo-czynnego ogółem i e) całkowite stężenie środka powierzchniowo-czynnego wynosi 80 g/l.
48
The composition according to p. 47, wherein the glyphosate or salt thereof is present in an amount of 50% to 76% by weight. 48. Kompozycja według zastrz. 47, znamienna tym, że zawiera glifozat albo jego sól w ilości 50% do 76% wagowych.
49
The composition according to p. The composition of 48, wherein the glyphosate or salt thereof is present in an amount of 60% to 72% by weight. 49. Kompozycja według zastrz. 48, znamienna tym, że zawiera glifozat albo jego sól w ilości 60% do 72% wagowych.
50
The composition according to p. The composition of 47, comprising glyphosate in the form of a salt thereof selected from the group consisting of ammonium salt, alkylamine salts, alkanolamine salts, alkylsulfonium salts, and glyphosate alkali metal salts. 50. Kompozycja według zastrz. 47, znamienna tym, że zawiera glifozat w postaci jego soli wybranej z grupy obejmującej sól amonową, sole alkiloaminowe, sole alkanoloaminowe, sole alkilosulfoniowe i sole metali alkalicznych glifozatu.
51
The composition according to p. 50, wherein the glyphosate is in the form of its ammonium salt. 51. Kompozycja według zastrz. 50, znamienna tym, że zawiera glifozat w postaci jego soli amonowej.
52
The composition according to p. 47, characterized in that it contains glyphosate or a salt thereof in an amount of 20% to 80% by weight, a surfactant of the chemical structure (i) in which R1 is a C8-C18 alkyl group, R2 is a linear propylene group, isopropylene or ethylene, R3 is ethylene, m is an average number from 1 to 5, and x + y is an average number from 2 to 20. 52. Kompozycja według zastrz. 47, znamienna tym, że zawiera glifozat, albo jego sól w ilości 20% do 80% wagowo, środek powierzchniowo-czynny o strukturze chemicznej (i), w której R1 oznacza grupę C8-C18-alkilową, R2 oznacza liniową grupę propylenową, grupę izopropylenową lub etylenową, R3 oznacza grupę etylenową, m oznacza przeciętną liczbę od 1 do 5, a x+y oznacza przeciętną liczbę od 2 do 20.
55
The composition according to p. 52, 53 or 54 which comprises a surfactant with a chemical structure in which m is 1. 55. Kompozycja według zastrz. 52, albo 53, albo 54, znamienna tym, że zawiera środek powierzchniowo-czynny o strukturze chemicznej w której m oznacza 1.
57
The composition according to p. The composition of 56 which comprises a surfactant with a chemical structure wherein x + y is an average number from 2 to 5. 57. Kompozycja według zastrz. 56, znamienna tym, że zawiera środek powierzchniowo-czynny o strukturze chemicznej, w której x+y oznacza przeciętną liczbę od 2 do 5. PL 193 095 B1 PL 193 095 B1
58
The composition according to p. 47, wherein the glyphosate or salt thereof is present in an amount from 20% to 80% by weight;a surfactant of the chemical structure (ii), where R1 is C8-C18-alkyl, R2 is a linear propylene, isopropylene or ethylene group, R3 is an ethylene group, R4 is methyl, m is an average number from 1 to 5, x + y is an average number from 0 to 20, and A- is an anion selected from the group consisting of halogen, phosphate and sulfate. 58. Kompozycja według zastrz. 47, znamienna tym, że zawiera glifozat albo jego sól w ilości od 20% do 80% wagowych;środek powierzchniowo-czynny o strukturze chemicznej (ii), w której R1 oznacza C8-C18-alkil, R2 oznacza liniową grupę propylenową, izopropylenową lub etylenową, R3 oznacza grupę etylenową, R4 oznacza metyl, m oznacza przeciętną liczbę od 1do 5, x+y oznacza przeciętną liczbę od 0do 20, a A- jest anionem wybranym z grupy składającej się z anionu chlorowca, fosforanu i siarczanu.
61
The composition according to p. 58, 59 or 60, wherein the surfactant has a chemical structure in which R2 is a linear propylene group and m is 1. 61. Kompozycja według zastrz. 58, albo 59, albo 60, znamienna tym, że zawiera środek powierzchniowo-czynny o strukturze chemicznej w której R2 oznacza liniową grupę propylenową, a m oznacza 1.
64
A concentrated herbicidal composition comprising an aqueous glyphosate solution, predominantly in the form of one salt thereof or a mixture of potassium and monoethanolammonium salts, the solution containing glyphosate in an amount greater than 350 g ae / l. 64. Kompozycja chwastobójcza stężona, znamienna tym, że zawiera wodny roztwór glifozatu, przeważająco w postaci jednej jego soli lub mieszaniny soli potasowej i monoetanoloamonowej, przy czym roztwór zawiera glifozat w ilości ponad 350 g a.e./l.
65
The composition according to p. 64. The pharmaceutical composition according to 64, comprising 350 to 500 g ae / l of glyphosate or a salt thereof. 65. Kompozycja według zastrz. 64, znamienna tym, że zawiera glifozat albo jego sól w ilości 350 do 500 g a.e./l.
66
The composition according to p. 65, characterized in that the monoethanolamine salt is present in an amount from 350 to 500 g ae / l. 66. Kompozycja według zastrz. 65, znamienna tym, że zawiera sól monoetanoloaminową w ilości od 350 do 500 g a.e./l.
67
The composition according to p. 65, characterized in that the potassium salt is contained in an amount from 350 to 500 g ae / l. 67. Kompozycja według zastrz. 65, znamienna tym, że zawiera sól potasową w ilości od 350 do 500 g a.e./l.
69
The composition according to p. 68, characterized in that the monoethanolamine salt is present in an amount from 450 to 500 g ae / l. 69. Kompozycja według zastrz. 68, znamienna tym, że zawiera sól monoetanoloaminową w ilości od 450 do 500 g a.e./l.
70
The composition according to p. 68, characterized in that the potassium salt is present in an amount from 450 to 500 g ae / l. 70. Kompozycja według zastrz. 68, znamienna tym, że zawiera sól potasową w ilości od 450 do 500 g a.e./l.
71
The composition according to p. 64, further comprising a surfactant. 71. Kompozycja według zastrz. 64, znamienna tym, że zawiera dodatkowo środek powierzchniowo-czynny.
73
The composition according to p. 72, characterized in that the monoethanolamine salt is present in an amount of 350 to 500 g ae / l. 73. Kompozycja według zastrz. 72, znamienna tym, że zawiera sól monoetanoloaminową w ilości 350 do 500 g a.e./l.
74
The composition according to p. 72, characterized in that the potassium salt is present in an amount of 350 to 500 g ae / l. 74. Kompozycja według zastrz. 72, znamienna tym, że zawiera sól potasową w ilości 350 do 500 g a.e./l.
76
The composition according to p. 75, characterized in that the monoethanamine salt is present in an amount of 450 to 500 g ae / l. 76. Kompozycja według zastrz. 75, znamienna tym, że zawiera sól monoetanoaminową w ilości 450 do 500 g a.e./l.
77
The composition according to p. 75, characterized in that the potassium salt is contained in an amount of 450 to 500 g ae / l. 77. Kompozycja według zastrz. 75, znamienna tym, że zawiera sól potasową w ilości 450 do 500 g a.e./l.
78
The composition according to p. 71, 72, or 73, or 74, or 75, or 76 or 77, further comprising a nonionic surfactant. 78. Kompozycja według zastrz. 71, albo 72, albo 73, albo 74, albo 75, albo 76, albo 77, znamienna tym, że dodatkowo zawiera niejonowy środek powierzchniowo-czynny.
84
The composition according to p. The composition of 83, wherein the nonionic surfactant is selected from the group consisting of a primary alcohol ethoxylate, secondary alcohol ethoxylate, sucrose alkyl ester, sorbitan alkyl ester and poly (alkyl glucoside). 84. Kompozycja według zastrz. 83, znamienna tym, że zawiera niejonowy środek powierzchniowo-czynny wybrany z grupy składającej się z pierwszorzędowego alkoholoetoksylanu, drugorzędowego alkoholoetoksylanu, estru alkilowego sacharozy, estru alkilowego sorbitanu i poli(glukozydu alkilu).
85
A method of controlling or controlling the growth of weeds or undesirable vegetation comprising the steps of:diluting the herbicidal composition in a convenient amount of water to form a spray solution, wherein the herbicidal composition comprises (a) glyphosate or a salt thereof;and (b) an effective herbicidal activity-promoting amount of a surfactant having the chemical structure (i) (R3-ABOUT)x-H 85. Sposób zwalczania lub regulacji wzrostu chwastów lub niepożądanej roślinności, znamienny tym, że obejmuje etapy: rozcieńczanie kompozycji chwastobójczej w dogodnej ilości wody z wytworzeniem roztworu do opryskiwania, przy czym kompozycja chwastobójcza obejmuje (a) glifozat albo jego sól;i (b) skutecznie wzmagającą aktywność chwastobójczą ilość środka powierzchniowo-czynnego mającego strukturę chemiczną (i) (R3-O)x-H RHo-RJ— n (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of 1 to 10, R2 in each group (O-R2) is independently C1-C4-alkylene, the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60 or the chemical structure (ii) (R3-O)x-H RHo-RJ— n (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1do 10, R2 w każdej z mgrup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby takie, że x+y wynosi od 2 do 60 lub strukturę chemiczną (ii) (R3-Ó)x-H 1 + — 1 + — R, - (OR,) - nR4 a (r3-o), - h in which R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average number from 1 to 10, R2 in each m group (O-R2) is independently C1-C4- alkylene, the R3 groups independently represent C1-C4-alkylene groups, R4 is a C1-C4-alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A- is an agriculturally acceptable anion or chemical structure (iii) (R.3-ABOUT)x-H R,-(O-R,)— n-R4 a (r3-o),-h w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22,m oznacza przeciętnąliczbę od 1do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, R4 oznacza grupę C1-C4-alkilową, x i y oznaczają przeciętne liczby takie, że x+y wynosi od 0 do 60, zaś A- oznacza anion dopuszczalny rolniczo, albo strukturę chemiczną (iii) (R3-O)x-H Rr (oR2) -N- ^ o (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average number from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group, R3 independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60;and applying a herbicidally effective amount of the spray solution to the foliage of weeds or undesirable vegetation. Rr(o-R2)-N-^o (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętnąliczbę od 1do 10, R2 w każdej z m grup (O-R2)niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby takie, że x+y wynosi od 2 do 60;i nakładanie skutecznej chwastobójczo ilości roztworu do opryskiwania na listowie chwastów albo niepożądanej roślinności.
86
A method of controlling or controlling the growth of weeds or undesirable vegetation comprising the steps of:dissolving or dispersing the herbicidal composition in a convenient amount of water to form a spray solution, wherein the herbicidal composition comprises (a) glyphosate or a salt thereof in an amount from 20% to 80% by weight, (b) an effective herbicide-promoting amount of a surfactant having the chemical structure (i) 86. Sposób zwalczania lub regulacji wzrostu chwastów lub niepożądanej roślinności, znamienny tym, że obejmuje etapy: rozpuszczania albo dyspergowania kompozycji chwastobójczej w dogodnej ilości wody z wytworzeniem roztworu do opryskiwania, przy czym kompozycja chwastobójcza zawiera (a) glifozat lub jego sól w ilości od 20% do 80% wagowo, (b) skutecznie wzmagającąaktywność chwastobójczą ilość środka powierzchn iowo-czyn nego mającego strukturę chemiczną (i) PL 193 095 B1 (R3-ABOUT)x-H Ri-CO-R,) - N (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60, or the chemical structure (ii) (R3-ABOUT) PL 193 095 B1 (R3-O)x-H Ri-CO-R,)—N (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby takie, że x+y wynosi od 2 do 60 albo strukturę chemiczną (ii) (R3-O) RHO-R ^ -nR4 (R3-O) wherein R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently C1-C4- alkylene, the R3 groups independently represent C1-C4-alkylene groups, R4 is a C1-C4-alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A- is an agriculturally acceptable anion or chemical structure (iii) (R.3-ABOUT)x-H RHO-R^—n-R4 (R3-O) w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, R4 oznacza grupę C1-C4-alkilową, x i y oznaczają przeciętne liczby takie, że x+y wynosi od 0 do 60, zaś A- oznacza anion dopuszczalny rolniczo, albo strukturę chemiczną (iii) (R3-O)x-H R .- (O-R2) ^ - n-> 0 (R3-ABOUT)y-H in which R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60;and applying a herbicidally effective amount of the spray solution to the foliage of weeds or undesirable vegetation. R.-(0-R2)^-n->0 (R3-O)y-H w której R1 oznacza grupę alkilową, arylową, albo alkiloarylową, o prostym albo rozgałęzionym łańcuchu C6 do C22, m oznacza przeciętną liczbę od 1 do 10, R2 w każdej z m grup (O-R2) niezależnie oznacza grupę C1-C4-alkilenową, grupy R3 niezależnie oznaczają grupy C1-C4-alkilenowe, zaś x i y oznaczają przeciętne liczby takie, że x+y wynosi od 2 do 60;i nakładania skutecznej chwastobójczo ilości roztworu do opryskiwania na listowie chwastów albo niepożądanej roślinności.
87
A method for controlling or controlling the growth of weeds or undesirable vegetation comprising:(a) diluting in a suitable amount of water a herbicidally effective amount of a herbicidal composition concentrated to form an application mixture, the herbicidal concentrated composition comprising an aqueous glyphosate solution predominantly in the form of one thereof. a salt or mixture of potassium or monoethanolammonium salt, the solution containing glyphosate in an amount greater than 350 g ae / L;(b) applying a mixture for application to foliage of plants. 87. Sposób zwalczania lub regulacji wzrostu chwastów lub niepożądanej roślinności, znamienny tym, że obejmuje: (a) rozcieńczanie w odpowiedniej ilości wody chwastobójczo skutecznej ilość kompozycji chwastobójczej stężonej do wytworzenia mieszaniny do stosowania, przy czym kompozycja chwastobójcza stężona zawiera wodny roztwór glifozatu przeważająco w postaci jednej jego soli lub mieszaniny soli potasowej lub monoetanoloamonowej, przy czym roztwór zawiera glifozat w ilości ponad 350 g a.e./l;(b) nakładanie mieszaniny do stosowania na listowie roślin.
89
The method according to p. 87 or 88, wherein the glyphosate or salt thereof is present in an amount from 350 to 500 g ae / L in the herbicidal concentrated composition. 89. Sposób według zastrz. 87, albo 88, znamienny tym, że glifozat albo jego sól jest obecna w ilości od 350 do 500 g a.e./l w kompozycji chwastobójczej stężonej.
92
The method according to p. 87 or 88, wherein the glyphosate or salt thereof is present in an amount of 450 to 500 g ae / L in the herbicidal concentrated composition. 92. Sposób według zastrz. 87, albo 88, znamienny tym, że glifozat albo jego sól jest obecna w ilości od 450 do 500 g a. e./l w kompozycji chwastobójczej stężonej.

Independent claims33

309 paragraphs in 20 sections, as filed

Description of the invention

The invention relates to a herbicidal composition and a method for controlling or regulating the growth of weeds or undesirable vegetation. These are new agriculturally acceptable N-phosphonomethylglycine (glyphosate) herbicide compositions containing tertiary and quaternary etheramines or etheramine oxides as surfactants.

Glyphosate is known to be a highly effective and commercially important herbicide useful in controlling the presence of a wide variety of undesirable vegetation, including agricultural weeds. Glyphosate is typically applied to the foliage of annual and perennial grasses, broadleaf plants and the like, dissolved in water, absorbed into the leaves for some time, and then transferred to the entire plant.

Typically, glyphosate is formulated in commercial compositions as a water-soluble salt. Commercially used salts include the ammonium salt, alkyl amine salts such as isopropyl amine, alkali metal salts such as the sodium salt, and trimethylsulfonium salt. However, glyphosate acid compositions are also used. Typical glyphosate salt compositions include aqueous concentrates requiring simple dilution and dilution with water for end user use, and dry water soluble or dispersible compositions, especially granules, requiring dissolution or dispersion in water prior to use.

Under the conditions of most applications, the herbicidal effectiveness of glyphosate can be greatly enhanced by including one or more surfactants in the composition to be applied. Such surfactants are believed to act in part to facilitate the penetration of glyphosate, a relatively hydrophilic compound, through the rather hydrophobic epithelium normally covering the outer ground parts of higher plants.

Wyrill and Burnside, Weed Science, Vol. 25 (1977), pp. 275-287, conducted extensive research on various classes of surfactants as herbicidal potentiators of glyphosate used as the isopropylamine salt. They showed that the selection of the surfactant had a marked effect on the herbicidal efficacy of glyphosate compositions, but in addition to showing the overall tendency of surfactants having high hydrophilic-lipophilic balance (HLB) values to be greater than surfactants of the same class having lower values, HLB, did not observe any prognostic relationship between the efficacy and the chemical class of the surfactant. Some of the most effective surfactants identified in the Wyrill and Burnside studies were ethoxylated tertiary and quaternary alkylamines.

Commercial glyphosate compositions often contained ethoxylated tertiary alkylamines as surfactants, e.g., ethoxylated alkylamine, a tallow fatty acid derivative, having an average of about 15 moles of ethylene oxide (EO) per mole of alkylamine. For many years, the Monsanto Company of St. Louis, Missouri, under the trademark Roundup® herbicide, sells glyphosate compositions containing various concentrations of such an ethoxylated alkylamine surfactant.

European Patent No. 0290416 to Forbes et al. discloses glyphosate salt compositions containing tertiary ethoxylated alkylamines surfactant having less than 15 moles of EO. For example, there is disclosed a composition comprising a glyphosate isopropylamine salt and, as a surfactant, an ethoxylated alkylamine, coconut fatty acid derivative having an average of 5 moles EO. Forbes et al. report that such compositions achieve certain herbicidal efficacy advantages over compositions having an EO content of the surfactant of about 15 moles.

European Patent No. 0274369 to Sato et al. discloses glyphosate compositions containing ethoxylated quaternary alkylamines as surfactants. Several examples are presented in which the surfactant is ethoxylated N-methylamine chloride, a derivative of coconut fatty acid, having 2 moles of EO.

A disadvantage of ethoxylated tertiary alkylamines as surfactants heretofore is that when present in concentrates in an amount corresponding to good herbicidal effectiveness, they tend to irritate the eyes. In some, but not all, cases, eye irritation can be reduced by converting a tertiary alkylamine to the equivalent (N-methyl) quaternary alkylamine. United States Patent Specification

PL 193 095 B1

No. 5,317,003 to Kassebaum discloses that a glyphosate composition containing an ethoxylated N-methylamine chloride surfactant, a coconut fatty acid derivative having 15 moles EO, is less irritating to the eyes than an otherwise identical composition wherein the surfactant is is an ethoxylated tertiary alkylamine, coconut fatty acid derivative, having 15 moles EO.

An alternative solution to the problem of eye irritation is suggested by US Patent No. 5,118,444 to Nguyen, in which ethoxylated tertiary amines as surfactants are converted to their N-oxides. Examples are given of glyphosate compositions wherein the surfactant is an ethoxylated alkylamine oxide of a tallow fatty acid having 10, 15 or 20 moles of EO.

A further disadvantage of ethoxylated tertiary alkylamines as surfactants heretofore is that when water is added thereto they tend to form a stiff gel which adds to the complexity and cost of making compositions containing such surfactants, making it difficult to clean the dishes. and pipes. In practice, this problem is dealt with by adding an anti-gelling agent, such as polyethylene glycol, to the surfactant.

Never before have tertiary and quaternary etheramines or etheramine oxides surfactants been disclosed as ingredients in concentrated glyphosate compositions.

United Kingdom Patent No. 1,588,079 to Texaco Development Corporation discloses examples of ethoxylated alkoxyisopropylamines and alkyl poly (isopropyl) amines as surfactants and methods for their preparation, and suggests that they are useful as detergents, dispersants, wetting agents, and emulsifiers. The disclosed surfactants have the usual chemical structure (CH2-H

RHocąąo-N ch3 (C 0, -H, wherein R 1 is a C 8 -C 18 -alkyl group, m is a number from 1 to 5, and x and y are average numbers such that x + y ranges from 2 to 20.

Tomah Products, Inc. of Milton, Wisconsin, in a pamphlet entitled Ethoxylated Amines, dated August 22, 1994, discloses, along with a series of ethoxylated tertiary alkylamines, a series of ethoxylated tertiary etheramines as surfactants having a typical structure (CH ^ O ^ -H

Rj -C0jy-H where Rl is C10-C26-alkyl, and x and y are average numbers such that x + y ranges from 2 to 15. Suggested uses for ethoxylated amines from Tomah include agricultural adjuvants. , known use of said ethoxylated tertiary alkylamines. It has not been suggested that the list of ethoxylated tertiary etheramines may be superior to ethoxylated tertiary alkylamines as agricultural adjuvants, nor is there any mention of making concentrated glyphosate compositions using ethoxylated tertiary etheramines.

Another brochure from Tomah Products entitled Quaternaries, dated September 1, 1994, lists a number of quaternary amines as surfactants in the list of quaternary amines as surfactants having a common chemical structure

PL 193 095 B1 (Ο ^ ανυ, -Η

Rvol - OCHjCHjCH ^ N-CHjC1 (CH2O4 -H wherein R1 is an aliphatic group, exemplified by an isodecyl or an isotridecyl group and x + y is 2. The list of suggested uses for the Tomah quaternary compounds does not include agricultural adjuvants.

Another brochure from Tomah Products entitled AO-14-2, dated August 24, 1994, discloses an ethoxylated etheramine oxide whose typical chemical structure can be deduced as (ch ^ o ^ -h

R1 is an aliphatic group, exemplified by the isodecyl group and x + y is 2. The list of suggested uses for AO-14-2 does not include agricultural adjuvants.

It is an object of the present invention to provide a novel herbicide glyphosate composition containing an etheramine surfactant which gives good herbicidal efficacy and little eye irritation.

It is a further object of the present invention to provide a commercial glyphosate formulation agent alternative to ethoxylated alkylamines surfactants that (1) eliminates or significantly reduces the need for an anti-gelling agent, (2) is soluble in aqueous compositions having higher acid equivalent levels. glyphosate than the existing compositions having comparable effectiveness, and (3) gives herbicidal efficacy better than that obtainable with comparable amounts of ethoxylated alkylamines having similar degrees of ethoxylation as surfactants.

It is further an object of the present invention to provide concentrated liquid and dry glyphosate etheramine surfactant compositions having good shelf life.

These and other purposes are fulfilled by the compositions disclosed herein.

According to the invention, the herbicidal composition is characterized in that it comprises (a) a herbicidally effective amount of glyphosate or a salt thereof; and (b) an effective herbicidal activity-promoting amount of a surfactant having the chemical structure (i) (R3-ABOUT)x-H5 - (OR,) - N (R5COy-H wherein R1 is a C6 to C22 straight or branched chain alkyl, aryl or alkylaryl group, m is an average of 1 to 10, R2 in each m groups (O-R2) independently represent a C1-C4-alkylene group, the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60 or the chemical structure (ii) (R3 -ABOUT)x-H Ri-io-R,) - no4 (R3-O)y-H in which R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups are independently C1-C4-alkylene groups, R4 is

A C1-C4-alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A- is an agriculturally acceptable anion or chemical structure (iii) (R3-0)x-H

Rx o (R3-ABOUT)y-H in which R1 is a C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group, the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers with x + y from 2 to 60.

The composition of the invention is preferably in the form of a spray solution (spray) made in situ by mixing in a tank of (a) a herbicidally effective amount of glyphosate or a salt thereof, (b) an effective herbicidal activity-promoting amount of one of the surfactants; (c) water.

In a preferred embodiment, the composition comprises glyphosate or a salt thereof and a surfactant dissolved in water, and is a ready-to-use composition.

The concentration of glyphosate or a salt thereof in the composition is preferably from 1 to 50 g ae / L, more preferably from 5 to 20 g ae / L. The composition comprises the surfactant preferably in an amount of 0.125% to 2% w / v.

In a further embodiment of the invention the composition is characterized in that it comprises glyphosate or a salt thereof in an amount of 5 to 20 g ae / l, a surfactant (s) in an amount of 0.125% to 2% w / v, glyphosate or a salt thereof, and a surfactant active dissolved in water and is a ready-to-use composition, and in the chemical structure of the surfactant, R1 is a C8-C18-alkyl group, R2 is a linear propylene, isopropylene or ethylene group, R3 is ethylene, m is an average number from 1 to 5, and x + y is an average number from 2 to 20. It preferably comprises a surfactant with a chemical structure in which R2 is linear propylene and m is 1.

In another preferred embodiment of the invention the composition is characterized in that it comprises glyphosate or a salt thereof in an amount of 5 to 20 g ae / l, a surfactant (ii) in an amount of 0.125% to 2% w / v, glyphosate or a salt thereof, and the surfactant dissolved in water and constitutes a ready-to-use composition, and in the chemical structure of said surfactant, R1 is a C8-C18-alkyl group, R2 is a linear propylene group, an isopropylene group or an ethylene group, R3 is an ethylene group, R4 is a methyl group, m is an average number from 1 to 5, x + y is an average number from 0 to 20, and A- is an anion selected from the group consisting of halogen anion, phosphate and sulfate. Preferably the surfactant has a chemical structure where R2 is a linear propylene group and m is 1.

In a further preferred embodiment the composition additionally comprises water and the glyphosate or salt thereof in an amount of from 50 to 500 g ae / l, preferably from 200 to 500 g ae / l, more preferably from 350 to 500 g ae / l, most preferably from 450 to 500 g ae / l. 500 g ae / l.

Another preferred composition of the present invention is characterized in that it comprises glyphosate in the form of a salt selected from the group consisting of ammonium salt, alkylamine salts, alkanolamine salts, alkylsulfonium salts and alkali metal salts of glyphosate, preferably in an amount from 200 to 500 g ae / l. more preferably in an amount of 350 to 500 g ae / l, especially in an amount of 450 to 500 g ae / l. A preferred glyphosate salt is an alkali metal salt, especially a potassium salt. Preferred glyphosate salts are also alkanolamine, monoethanolamine, alkylsulfonium, including trimethylsulfonium, isopropylamine salt.

The composition of the invention preferably additionally comprises a second surfactant selected from the group consisting of primary or secondary alcohol ethoxylates, alkyl sucrose or sorbitan esters, or polyalkyl glucoside.

In a further embodiment of the invention the composition is characterized in that it further comprises water, glyphosate or a salt thereof in an amount of 50 to 500 g ae / l, and in the chemical structure of the surfactant (i) R1 is C8-C18 alkyl, R2 is linear propylene group, isopropyl 6

In the case of either a new or ethylene group, R3 is an ethylene group, m is an average number from 1 to 5 and x + y is an average number from 2 to 20, this composition being in a concentrated liquid form. In this composition, the weight ratio of surfactant to glyphosate ae is from 1:20 to 1: 1, more preferably from 1:10 to 1: 2. Wherein preferably the surfactant has a chemical structure where m is 1, more preferably the surfactant has a chemical structure where R 1 is a straight or branched chain alkyl having 10 to 15 carbon atoms and x + y is the average number from 2 to 10, more preferably x + y is an average number from 2 to 5.

In one preferred embodiment of the invention, the composition is further characterized in that it further comprises 50 to 500 g ae / l of water, glyphosate or a salt thereof in the chemical structure of the surfactant (ii) R1 is C8-C18 alkyl, R2 is linear a propylene group, an isopropylene group or an ethylene group, R3 is an ethylene group, R4 is a methyl group, m is an average number from 1 to 5, x + y is an average number from 0 to 20, and A- represents an anion selected from the group consisting of halogen anion, phosphate and sulfate, wherein the composition is in a concentrated liquid form. In this embodiment, the weight ratio of surfactant to glyphosate ae is preferably from 1:20 to 1: 1, more preferably from 1:10 to 1: 2. In contrast, the surfactant preferably has a chemical structure where R2 is a linear propylene group, m is 1, more preferably has a chemical structure where R1 is a straight or branched alkyl chain having 10 to 15 carbon atoms and x + y is an average a number from 2 to 10, more preferably from 2 to 5.

Another preferred composition of the invention is characterized in that it additionally comprises water, (a) glyphosate in the form of its isopropylamine or trimethylsulfonium salt at a concentration of 450 to 500 g ae / l; b) a surfactant with the chemical structure (i) in which R1 is C8-C18-alkyl, R2 is a linear propylene, isopropylene or ethylene group, R3 is an ethylene group, m is from 1 to 5, (c) and the ratio glyphosate by weight ae to surfactants in total is from 5: 1 to 8: 1; and (d) the above surfactant constitutes from 75% to 100% by weight of the total surfactant present, wherein the composition is in a stable liquid form.

Another preferred composition of the present invention is characterized in that it additionally comprises water, (a) glyphosate in the form of its isopropylamine or trimethylsulfonium salt at a concentration of 450 to 500 g ae / l; b) a surfactant of the chemical structure (ii), wherein R1 is C8-C18-alkyl, R2 is a linear propylene, isopropylene or ethylene group, R3 is an ethylene group, R4 is methyl, m is an average number from 1 to 5 , x + y is an average number from 0 to 20, and A- is an anion selected from the group consisting of a halogen, phosphate and sulfate anion; (c) the above surfactant is from 75% to 100% by weight of the total surfactant present; and (d) the weight ratio of glyphosate ae to total surfactants is from 5: 1 to 8: 1, with the composition being in a stable liquid form. The composition preferably comprises (a) glyphosate in the form of its isopropylamine salt at a concentration of 480 g ae / l; b) a surfactant with a chemical structure in which R1 is a straight or branched alkyl group from 10 to 15 carbon atoms, R2 is an isopropylene or ethylene group, and x + y is an average number from 2 to 5; (c) the above surfactant is about 80% by weight of the total surfactant present (d) additionally contains about 20% by weight of the total surfactant present e) the total surfactant concentration is 80 g / l, more preferably comprises (a) glyphosate in the form of its isopropylamine salt at a concentration of 480 g ae / l; b) a surfactant with a chemical structure in which R1 is a straight or branched alkyl group from 10 to 15 carbon atoms, R2 is a linear propylene group, m is 1, and x + y is an average number from 2 to 5; (c) the above surfactant is about 80% by weight of the total surfactant present, and (d) additionally comprises about 20% by weight of the total surfactant present, and e) the total concentration of surfactant is 80 g / l.

The dry concentrated composition of the present invention comprises a herbicidally effective amount of glyphosate or a salt thereof in an amount of 20% to 80% by weight, preferably an amount of 50% to 76% by weight, most preferably an amount of 60% to 72% by weight. The composition preferably comprises glyphosate in the form of a salt thereof selected from the group consisting of ammonium salt, alkylamine salts, alkanolamine salts, alkylsulfonium salts, and alkali metal salts of glyphosate, preferably in the form of its ammonium salt. The dry concentrated composition preferably comprises a glyphosate or salt thereof in an amount of 20% to 80% by weight of the agent

Is a surfactant of the chemical structure (i), in which R1 is a C8-C18-alkyl group, R2 is a linear propylene group, isopropylene or ethylene group, R3 is an ethylene group, m is an average number from 1 to 5, and x + y is an average number from 2 to 20, wherein the weight ratio of surfactant to glyphosate ae is from 1:20 to 1: 1, more preferably from 1:10 to 1: 2. This dry concentrated composition preferably comprises a surfactant having a chemical structure in which m is 1, preferably a chemical structure in which R1 is a straight or branched alkyl group of 10 to 15 carbon atoms and x + y is an average number from 2 to 10, preferably from 2 to 5.

In another embodiment, the dry concentrated composition comprises glyphosate or a salt thereof in an amount from 20% to 80% by weight; a surfactant of the chemical structure (ii), where R1 is C8-C18-alkyl, R2 is a linear propylene, isopropylene or ethylene group, R3 is an ethylene group, R4 is methyl, m is an average number from 1 to 5, x + y is an average number from 0 to 20, and A- is an anion selected from the group consisting of halogen, phosphate and sulfate anion, preferably the weight ratio of surfactant to glyphosate ae is from 1:20 to 1: 1, more preferably from 1:10 to 1: 2. Whereas the surfactant preferably has a chemical structure where R2 is a linear propylene group, and m is 1, more preferably the surfactant has a chemical structure where R1 is a straight or branched alkyl group of 10 to 15 carbon atoms, and x + y represents an average number from 2 to 10, preferably from 2 to 5.

In yet another embodiment, the concentrated herbicidal composition is characterized in that it comprises an aqueous glyphosate solution, predominantly in the form of one salt thereof or a mixture of potassium and monoethanolammonium salts, the solution containing glyphosate in an amount greater than 350 g ae / l, preferably in an amount of 350 to 500 g ae / l, more preferably contains the monoethanolamine salt in an amount of 350 to 500 g ae / l, especially the potassium salt in an amount of 350 to 500 g ae / l.

In a preferred embodiment, the herbicidal concentrated composition comprises the potassium salt, the monoethanolamine salt or a mixture of the potassium salt and the monoethanolamine salt of glyphosate in an amount of 450 to 500 g ae / l, preferably the monoethanolamine salt in an amount of 450 to 500 g ae / l, especially potassium salt in an amount of 450 to 500 g ae / l.

In a further embodiment, the herbicidal concentrated composition further comprises a surfactant. Preferably it contains glyphosate or its salt in an amount of 350 to 500 g ae / l, more preferably the monoethanolamine salt in an amount of 350 to 500 g ae / l, and especially the potassium salt in an amount of 350 to 500 g ae / l. Further, this composition preferably contains the potassium salt, monoethanolamine salt or a mixture of potassium and monoethanolamine salt of glyphosate in an amount of 450 to 500 g ae / l, and especially contains the monoethanamine salt in an amount of 450 to 500 g ae / l or a potassium salt in an amount of 450 to 500 g. ae / l. In addition, it preferably contains a nonionic surfactant. This nonionic surfactant is selected from the group consisting of primary alcohol ethoxylate, secondary alcohol ethoxylate, sucrose alkyl ester, sorbitan alkyl ester and poly (alkyl glucoside). The nonionic surfactant is preferably an alkyl polyglucoside.

The herbicidal composition according to the invention is characterized in that it preferably additionally comprises a second surfactant selected from the group consisting of primary or secondary alcohol ethoxylates, alkyl sucrose or sorbitan esters, and poly (alkyl glucoside). As the alkylsulfonium group it preferably contains a trimethylsulfonium group. Wherein the surfactants together are present in a herbicidally effective amount.

The invention also relates to a method of controlling or regulating the growth of weeds or undesirable vegetation comprising the steps of: diluting the herbicidal composition in a convenient amount of water to form a spray solution, wherein the herbicidal composition comprises (a) glyphosate or a salt thereof; and (b) an effective herbicidal activity-promoting amount of a surfactant having the chemical structure (i) (R3-0)x-H

RriO-R,) - N (R3-O)y-H

In which R1 is a straight or branched chain C6 to C22 alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently C1-C4 -alkylene, the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60, or the chemical structure (ii) (R3-ABOUT)x-H l + -

RrCO-R,) - nR4 a (Ry-O)y-H in which R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups independently represent C1-C4-alkylene groups, R4 is a C1-C4-alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A- is an agriculturally acceptable anion or chemical structure (iii) (R.3-ABOUT)x-H

N-> 0 (R3-0)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of 1 to 10, R2 in each group (O-R2) is independently C1-C4-alkylene, the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60; and applying a herbicidally effective amount of the spray solution to the foliage of weeds or undesirable vegetation.

The method of controlling or controlling the growth of weeds or undesirable vegetation of the invention comprises the steps of: dissolving or dispersing the herbicidal composition in a convenient amount of water to form a spray solution, wherein the herbicidal composition comprises (a) glyphosate or a salt thereof in an amount from 20% to 80% by weight, (b) an effective herbicidal activity-promoting amount of a surfactant having the chemical structure (i) (^ -Ο)χ-Η

RriO-RJ— N (R3-ABOUT)y-H in which R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group, the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60, or the chemical structure (ii) (^ -Ο)χ-Η

R, - (o-R2> - nR. A (R, -O), - H in which R1 is a C6 to C22 straight or branched chain alkyl, aryl or alkylaryl group, m is an average number from 1 to 10, R2 in each m group (O-R2) independently represents a C1-C4-alkylene group, the R3 groups independently represent a C1-C4-alkylene group, R4 is a C1-C4-alkyl group, x and y are average numbers such that x + y is from 0 to 60, and A.- denotes an agriculturally acceptable anion,

PL 193 095 B1 or the chemical structure (iii) (R3-ABOUT)x-H

N ^ O (R3-ABOUT)y-H where R1 is a straight or branched C6 to C22 straight or branched alkyl, aryl or alkylaryl group, m is an average number from 1 to 10, R2 in each m group (O-R2) is independently a C1-C4-alkylene group , the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers such that x + y is from 2 to 60; and applying a herbicidally effective amount of the spray solution to the foliage of weeds or undesirable vegetation.

In another embodiment of the invention, the method of controlling or regulating the growth of weeds or undesirable vegetation is characterized in that it comprises: (a) diluting a herbicidally effective amount of a herbicidal effective amount of a concentrated herbicidal composition to form an application mixture in a suitable amount of water, wherein the concentrated herbicidal composition comprises an aqueous glyphosate solution predominantly as one salt thereof or a mixture of potassium or monoethanolammonium salt, the solution containing more than 350 g ae / l; (b) applying a mixture for application to foliage of plants. In this method, the herbicidal composition additionally comprises a surfactant, glyphosate or salt thereof, preferably in an amount of 350 to 500 g ae / L, preferably glyphosate monoethanolammonium salt in a concentration of 350 to 500 g ae / L, more preferably potassium glyphosate salt in at a concentration of 350 to 500 g ae / l. In a further preferred embodiment of this method, the herbicidal concentrated composition comprises glyphosate or a salt thereof in an amount from 450 to 500 g ae / l. In a more preferred embodiment of the process, the herbicidal concentrated composition comprises glyphosate monoethanolammonium salt at a concentration of 450 to 500 g ae / L, preferably potassium glyphosate salt at a concentration of 450 to 500 g ae / L.

Novel herbicide compositions containing glyphosate or a salt thereof and an etheramine surfactant, referred to as an etheramine surfactant, in which the hydrophobic moiety is attached to the amino group through a series to about 10 oxyalkylene groups.

The compositions of the invention can be prepared in situ by the end user shortly before application to the foliage of vegetation to be killed or reduced by mixing in an aqueous solution the glyphosate composition and the surfactant-containing composition having a chemical structure embraced by the structures outlined just above. Such compositions of the invention are referred to herein as tank-mix compositions.

Alternatively, the compositions of the invention may be provided to the end user as ready-made preparations, either at the dilution desired for use (ready-to-use compositions) or requiring dilution, dispersion or dissolution in water (concentrates). The compositions of the invention so prepared are storage stable and may be liquid or dry.

The compositions of the invention may include glyphosate in the form of an acid. However, due to the relatively low water solubility of glyphosate acid, more soluble glyphosate salts are generally preferred. As in previous commercial compositions, a particularly preferred salt for the aqueous compositions of the invention is the isopropylamine salt of glyphosate, and a particularly preferred salt for the dry compositions of the invention is the ammonium salt. Many other salts can be used in aqueous or dry compositions, including, but not limited to, alkylamine glyphosate salts such as dimethylamine and n-propylamine, alkanolamine salts such as monoethanolamine, alkyl sulfonium salts such as trimethyl sulfonium, and alkali metal salts such as sodium and potassium. Regardless of whether an acid or a salt is used, it is generally preferable to refer to the amount of glyphosate given or included in the composition in terms of glyphosate acid equivalent, commonly abbreviated as ae (acid equivalent).

The tank mix and ready-to-use compositions of the invention are aqueous solutions containing from about 1 to about 50 g ae / L glyphosate, occasionally more. A preferred range for tank-mix and ready-to-use compositions is from about 5 to about 20 g ae / L.

The compositions of the invention may be aqueous solutions containing from about 50 to about 500 g

ae / L of glyphosate or greater, preferably from about 200 to about 500 g ae / L, and most preferably from about 350 to about 500 g ae / L. An example of a particularly preferred aqueous concentrate according to the invention is comprised of

The formulation contains glyphosate isopropylamine salt at a content of about 360 g ae / L, the same as present in commercial compositions sold as Roundup® herbicide by Monsanto Company.

A surprising advantage of the aqueous compositions of the invention over those previously used is that the glyphosate concentration can be increased to very high levels, e.g. from about 450 to about 500 g ae / l, and the surfactant concentration still remains appropriate for excellent herbicidal efficacy. without requiring the end user to add more surfactant to the nebulizer reservoir. Many such highly concentrated compositions have excellent shelf life over a wide range of temperature conditions.

Alternatively, the compositions of the invention may be dry formulations, presented, for example, as powders, pills, tablets or, preferably, granules, to be dispersed or dissolved in water before use. Typically such compositions are free from water-insoluble components in appreciable amount, and thus the compositions are fully soluble. The water-soluble or dispersible dry compositions of the invention contain from about 20% to about 80% by weight of ae glyphosate, preferably from about 50% to about 76%, and most preferably from about 60% to about 72%. An example of a particularly preferred, water-soluble granular composition of the invention comprises glyphosate ammonium at a content of about 72% by weight, the same as present in commercial compositions sold as the Scout® herbicide by Monsanto Corapany.

In the dry compositions of the invention, glyphosate itself may form a vehicle for other formulation ingredients, or one or more inert ingredients providing such vehicle may additionally be present. An example of an inert support that can be used is ammonium sulfate. The term "dry" as used herein does not imply that the dry compositions are completely anhydrous; typically the dry compositions of the invention contain from about 0.5 to about 5 percent by weight, preferably less than about 1 percent by weight, of water.

Dry granular formulations, soluble or dispersible in water, can be prepared by any method known in the art, including, but not limited to, spray drying, fluidized bed agglomeration, pan granulation, or extrusion. In dry compositions, glyphosate can be present as a salt, e.g., a sodium or potassium salt, or as an acid. Compositions containing acid glyphosate may optionally contain an acid acceptor such as an alkali metal or ammonium carbonate or bicarbonate, ammonium dihydrogen phosphate or the like such that when dissolved or dispersed in water by the end user, a water-soluble glyphosate salt is produced.

The compositions of the present invention are distinguished from all previously described glyphosate compositions by the presence of alkoxylated tertiary or alkoxylated or non-alkoxylated quaternary etheramines or an alkoxylated etheramine oxide surfactant having the usual chemical structure (i) (R3-0)x-H rand - (O-RJ — N (R3-ABOUT)y-H where R1 is a straight or branched C6 to about C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to about 10, R2 in each m group (O-R2) is independently C1-C4-alkylene , the R3 groups are independently C1-C4-alkylene groups, and x and y are average numbers such that x + y ranges from 2 to about 60; or (ii) (R.3-ABOUT)x-H

I + -

Ri-iO-Ra) -NR4 A (R3-O)y-H where R1 is a straight or branched C6 to about C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to about 10, R2 in each m group (O-R2) is independently C1-C4-alkylene , the R3 groups are independently C1-C4-alkylene groups, R4 is a C1-C4-alkyl group, x and y are average numbers such that x + y ranges from 0 to about 60, and A- is an agriculturally acceptable anion; or (iii)

PL 193 095 B1 (R3-ABOUT)x-H RriO-R,) - N-> 0 (R3-ABOUT)y-H where R1 is a straight or branched C6 to about C22 straight or branched alkyl, aryl or alkylaryl group, m is an average of from 1 to about 10, R2 in each m group (O-R2) is independently C1-C4- alkylene, the R3 groups independently represent C1-C4-alkylene groups, and x and y are average numbers such that x + y ranges from 2 to about 60.

Alkylamines or alkylamine oxides as surfactants used so far do not have (O-R2) groups, in other words m = 0. We have found that glyphosate compositions can be given remarkably improved properties when 1 to about 1 is inserted in the surfactant structure. 10 groups (O-R2) between the R1 group and the nitrogen atom.

Aryl groups, if present in R1, have 5-7, preferably 6, carbon atoms and may or may not be substituted with moieties. The alkyl portion of any alkylaryl group constituting R1 has 1-16 carbon atoms. An example of such an alkylaryl group is an alkylphenyl group, e.g. nonylphenyl.

However, in the preferred surfactants of the invention, R 1 is a straight or branched alkyl group having about 8 to about 18, e.g. about 10-15, carbon atoms, and is derived from the appropriate alcohol. For example, the alkyl group may be of natural origin such as coconut or tallow, or may be derived from a synthetic alcohol such as isodecyl alcohol, isotridecyl alcohol, linear C 12 -C 14 alcohols or octadecyl alcohol.

The immediate R2 substituent of the nitrogen atom (the closest R2 group) is in preferred examples a linear propylene (-CH2CH2CH2-), isopropylene (-CH2CH2CH (CH3) -) or ethylene (-CH2CH2-) group. Preferred examples where the closest R2 group is a linear propylene group have m = 1. When the closest R2 group is an isopropylene or ethylene group, m preferably ranges from 1 to 5, most preferably from 2 to 3, and all R2 groups are preferably such themselves.

The R3 substituents in the preferred examples are independently selected from isopropylene and ethylene. In particularly preferred examples, all R3 groups are ethylene. In the tertiary etheramines and etheramine oxides of the invention it is preferred that x + y is in the range of 2 to about 20. In the quaternary ether amines of the invention it is preferred that x + y is in the range of 0 to about 20.

A particularly preferred range for x + y in the tertiary and quaternary etheramines and etheramine oxides of the invention is from 2 to about 10, more particularly from 2 to about 5.

In the quaternary etheramines of the invention, R 4 is preferably a methyl group and Ais preferably a halogen anion, e.g. chloride or bromide, phosphate or sulfate ion, or alternatively may be a glyphosate ion or may be contributed by an anionic surfactant included with the etheramine in the composition. It will be appreciated by those skilled in the art that at the low pH that can exist in a glyphosate composition, the tertiary etheramines most likely will be protonated at the nitrogen atom and may be associated with the counterion; in such cases, the tertiary etheramine can be represented by the chemical structure shown above for the quaternary etheramine with the exception that R4 is hydrogen. Counterion A.- the low pH glyphosate composition containing the tertiary etheramine is most likely glyphosate itself.

A particularly preferred surfactant useful in the compositions of the invention is a tertiary etheramine, wherein R1 = C12-C14 alkyl group, R2 = isopropylene group, m = 2, R3 = ethylene group, and x + y = 5.

Another particularly preferred surfactant useful in the compositions of the invention is a tertiary etheramine, wherein R1 = C12-C14-alkyl group, R2 = ethylene group, m = 3, R3 = ethylene group, and x + y = 5.

Two other particularly preferred surfactants useful in the compositions of the invention are tertiary etheramines, wherein R1 = isodecyl, R2 = linear propylene, m = 1, R3 = ethylene, and x + y = 2 or 5, respectively.

Another series of particularly preferred surfactants useful in the compositions of the present invention is a tertiary etheramine, wherein R 1 = the alkyl group derived from

Coconut fatty acid, R2 = linear propylene group, m = 1, R3 = ethylene group, and x + y = a number ranging from 2 to 10.

Two other particularly preferred surfactants useful in the compositions of the invention are tertiary etheramines, wherein R1 = triisodecyl group, R2 = linear propylene group, m = 1, R3 = ethylene group, and x + y = 2 or 5, respectively.

Two other particularly preferred surfactants useful in the compositions of the present invention are quaternary etheramines where R1 = isodecyl or triisodecyl group, respectively, R2 = linear propylene group, m = 1, R3 = ethylene group, and x + y = 2.

Any convenient and effective means may be used in the compositions of the invention amount of the etheramine surfactant . Very high levels of surfactant, e.g., up to 5% or even greater, are achievable in tank-mix and ready-to-use compositions, but for economic reasons it will be more normal to use a concentration ranging from about 0.125% to about 2%. The skilled artisan will be able to determine from tests on various plant species the appropriate content of etheramine surfactant to be included in any particular glyphosate application.

In liquid or dry concentrates of the invention, the etheramine surfactant is preferably in a weight ratio to ae of glyphosate in the range from about 1:20 to about 1: 1, most preferably from about 1:10 to about 1: 2, e.g. about 1 : 6.

Long-term storage stability is an important attribute of concentrates. In the case of aqueous concentrated glyphosate salt compositions, it is especially important that the surfactants in the formulation do not separate from the other ingredients as a separate phase. Many of the aqueous concentrates made from the surfactants used heretofore show a tendency towards phase separation at high temperatures. The etheramine surfactants disclosed herein have the property of exhibiting good compatibility with glyphosate salts, in particular with isopropylamine salt, as evidenced by relatively high cloud points even in aqueous solutions having high glyphosate concentrations. In general, a cloud point above about 50 ° C is desirable for most applications.

In addition to glyphosate or a salt thereof and an etheramine surfactant, any of a variety of further ingredients or adjuvants may be included in the compositions of the present invention, as long as such added materials do not clearly antagonize the herbicidal activity of glyphosate. Examples of such added materials for illustration include anti-gelling agents, anti-freeze agents, thickeners, dyes, antimicrobial preservatives, or additives to further increase herbicidal activity, such as ammonium sulfate or fatty acids.

A second surfactant belonging to the class other than etheramines may also be included, e.g. a primary or secondary alcohol ethoxylate, an alkyl ester of sucrose or sorbitan, or an alkyl polyglucoside. When such a second surfactant is present, it is preferred that the weight ratio of the etheramine to the second surfactant is greater than about 1: 1, most preferably greater than about 2: 1, e.g., about 4: 1.

Preferably, when the second surfactant is included in a highly concentrated glyphosate composition, e.g., containing about 450 to about 500 g ae / L, the etheramine surfactant comprises at least about 75% by weight of all surfactants present.

Mixtures of glyphosate with other herbicides are also within the scope of the present invention when an etheramine surfactant is included in the composition. Examples of such other herbicides include bialaphos, glufosinate, 2,4-D, MCPA, dicamba, diphenyl ethers, imidazolinones, and sulfonylureas.

Methods for using glyphosate compositions are well known to those skilled in the art. The aqueous concentrates of the invention are diluted in the correct amount of water and applied, e.g. by spraying, to weeds or other undesirable vegetation to be killed or reduced. The dry concentrates of the invention are dissolved or dispersed in the correct volume of water and administered in the same manner. For most purposes, compositions of the invention are administered in ae amounts glyphosate in the range of about 0.1 to about 5 kg / ha, sporadically more. Typical glyphosate ae amounts for reducing annual and perennial grasses and broadleaf plants range from about 0.3 to about 1.5 kg / ha. The compositions of the invention may be administered in any convenient amount of water, most typically in the range of from about 50 to about 1000 L / ha.

The present invention is illustrated, but not limited, by the following examples.

Examples

Cloud point for some of the liquid compositions in the Examples was determined as follows. A sample of the composition in a test tube was heated in a water bath until it turned cloudy. The tube was then removed from the water bath and the sample was stirred with a thermometer until it became clear. The temperature at which the sample turned clear was recorded as the cloud point of the composition.

The percentages expressed as% in the following examples are by weight unless otherwise indicated.

Example 1

The surfactant used in Example 1 is a tertiary etheramine having the chemical structure shown above in which R1 is a C12-C14 alkyl group, m is 3, x + y is 5, and R2 and R3 are each ethylene.

The aqueous concentrate in Example 1 was prepared by mixing the following ingredients in the order given:

(1) An aqueous solution of glyphosate isopropylamine salt containing 46% glyphosate ae, 67.4 g.

(2) a surfactant as defined above, 10.0 g.

(3) demineralized water, 22.6 g.

It can be calculated that the composition comprises 31% glyphosate ae and 10% surfactant. The specific gravity of the composition at 20 / 15.6 ° C was found to be 1.1628. Cloud point of the composition was> 90 ° C.

Example 2

The surfactant used in Example 2 is the same as used in Example 1. The aqueous concentrate in Example 2 was prepared by mixing the following ingredients in the order given:

(1) An aqueous solution of glyphosate isopropylamine salt containing 46% glyphosate ae, 1348 g.

(2) a surfactant as defined above 110 g.

(3) demineralized water, 542 g.

It can be calculated that the composition comprises 31% glyphosate ae and 5.5% surfactant. The specific gravity of the composition at 20 / 15.6 ° C was found to be 1.1630. Cloud point of the composition was> 90 ° C.

The composition of Example 2 was tested for eye irritation following the standard procedure in US Environmental Protection Agency (EPA) 540 / 9-82-025, November 1982, entitled Pesticidal Assessment Guidelines, Subchapter F, Hazard Evaluation : Human and Domestic Animals. The study was conducted in accordance with the EPA Good Laboratory Practice (GLP) standards. The results obtained placed the composition in toxicity category III, indicating low eye irritation.

Example 3

The surfactant used in Example 3 is a tertiary etheramine having the chemical structure shown above in which R1 is a C12-C14 alkyl group, m is 2, x + y is 5, R2 is isopropylene and R3 is ethylene.

The aqueous concentrate in Example 3 was prepared by mixing the following ingredients in the order given:

(1) An aqueous solution of glyphosate isopropylamine salt containing 46% glyphosate ae, 1348 g.

(2) a surfactant as defined above, 200 g.

(3) demineralized water, 452 g.

It can be calculated that the composition comprises 31% glyphosate ae and 10% surfactant. The specific gravity of the composition at 20 / 15.6 ° C was found to be 1.1618. Cloud point of the composition was> 90 ° C.

Example 4

The surfactant used in Example 4 is the same as that used in Example 3. The aqueous concentrate in Example 4 was prepared by mixing the following ingredients in the order shown:

(1) An aqueous solution of glyphosate isopropylamine salt containing 46% glyphosate ae, 1348 g.

(2) a surfactant as defined above 110 g.

(3) demineralized water, 542 g.

PL 193 095 B1

It can be calculated that the composition comprises 31% glyphosate ae and 5.5% surfactant. The specific gravity of the composition at 20 / 15.6 ° C was found to be 1.1617. Cloud point of the composition was> 90 ° C.

The composition of Example 4 was tested for eye irritation following the standard procedure prescribed in EPA publication 540 / 9-82-025, November 1982, cited above. The study was conducted in accordance with GLP standards. The results obtained placed the composition in toxicity category III, indicating low eye irritation.

Examples 5-7

The surfactants used in Examples 5-7 are tertiary etheramines having the chemical structure shown above in which R1 is a C12-C14 alkyl group, m is 3 and R2 and R3 are each ethylene. The value of x + y changes as shown in the table below.

Aqueous concentrates containing 31% glyphosate ae as isopropylamine salt and 11% surfactant were prepared by a procedure similar to Examples 1-4. Cloud point of each composition was determined as shown in the table below.

<td>Example</td><td>x + y</td><td>Cloud point (° C)</td>

Examples 8-11

The surfactants used in examples 8-11 are tertiary etheramines having the chemical structure shown above, wherein R1 is a C12-C14 alkyl group, m is 2, R2 is an isopropylene group and R3 is an ethylene group. The value of x + y changes as shown in the table below.

<td>Example</td><td>x + y</td><td>Cloud point (° C)</td>

Example 12

Comparative herbicidal efficacy was determined in a Jerseyville, Illinois test field. The treatments were applied after the plants germinated from seeds planted mechanically in rows. A randomized block design with three replications was used. Spraying was performed with a multi-nozzle knapsack spray with overlapping spray fields to maximize uniformity of coverage. Herbicidal efficacy was assessed as the visually estimated percent reduction compared to untreated plots.

The plant species on which the herbicidal efficacy was assessed were one-sided weed (Echinochloa crus-galli, ECHCF), broadleaf signalgrass (Brachiaria platyphylla, BRAPP), prickly sida (Sida spinosa, SIDSP), rough amaranth (Amaranthus retroflexus, AMAREpania) (Sesbania exaltata, SEBEX), bindweed (Ipomoea sp., IPOSS) and velvetleaf (Abutilon theophrasti, ABUTH).

All glyphosate compositions in this test were aqueous concentrates diluted with water to a spray volume of 93 L / ha. Dilutions were made to give three spray rates of 314, 628, and 840 g ae / ha glyphosate for each formulation.

The model treatments used as a reference in this field test were performed using concentrates A and B containing 360 g ae / l of glyphosate isopropylamine salt and 15.4% and 7.7% respectively MON 0818, a surfactant based on an ethoxylated alkylamine derivative of the acid tallow fat averaging 15 moles EO.

The CJ concentrates of the invention contained glyphosate in the form of the isopropylamine salt in an amount of 360 g ae / l. The CF concentrates further contained, as the sole surfactant, a tertiary etheramine having the chemical structure shown above, wherein R1 is a C12-C14 alkyl group, m is 2, x + y is 5, R2 is an isopropylene group and R3 is ethylene. The contents of the surfactant in concentrates C, D, E and F were respectively 3.5%, 5.5%, 7.5%

PL 193 095 B1 and 10%. Concentrates D and F are substantially identical to the compositions of Examples 4 and 3 above, respectively. The GJ concentrates contained, as the sole surfactant, a tertiary etheramine having the chemical structure shown above in which R1 is a C12-C14 alkyl group, m is 3, x + y is 5, and R2 and R3 are each ethylene. The surfactant contents in the G, H, I and J concentrates were respectively 3.5%, 5.5%, 7.5% and 10%. Concentrates H and J are substantially identical to the compositions of Examples 2 and 1 above, respectively.

The concentrates K and L of the invention contained glyphosate in the form of an isopropylamine salt in an amount of 420 g ae / l and as a surfactant a tertiary etheramine having the chemical structure shown above, in which R1 is a C12-C14 alkyl group, m is 3, x + y is 5 and R2 and R3 are each ethylene. The contents of the etheramine surfactant in the K and L concentrates were 5.5% and 3.5%, respectively. Concentrate L further contained as a surfactant 3.9% poly (alkyl glucoside) having a C9-C11 alkyl chain and an alkyl / glucose molar ratio of 1: 1.6.

The field test results are summarized in the table below.

<td colspan="9">Percentage of reduction</td>

<td colspan="2">G ae / ha composition</td><td>ECHCF</td><td>BRAPP</td><td>SIDSP</td><td>AMARE</td><td>SEBEX</td><td>IPOSS</td><td>ABUTH</td>

PL 193 095 B1 cont. table

Example 13

The surfactant used in Example 13 is the same as that used in Example 1. The dry water-soluble glyphosate composition of Example 13 in the form of granules was prepared by adding the following ingredients to a small food processor:

(1) powdered ammonium glyphosate containing 86.6% glyphosate ae, 37.5 g.

(2) a surfactant as defined above, 12.5 g.

(3) water, 2.5 g.

No gelation of the surfactant was observed. The ingredients are mixed to form homogeneous small granules. The granules were dried in a fluid bed dryer at 65 ° C for 15 minutes.

It can be calculated that the composition comprises 25% surfactant by dry weight. The determined glyphosate content was 61.8% ae

Example 14

The surfactant used in Example 14 is the same as that used in Example 3. A dry water-soluble glyphosate composition of glyphosate granules was prepared by adding the following ingredients to a small food processor:

(1) powdered ammonium glyphosate containing 86.6% glyphosate ae, 37.5 g.

(2) a surfactant as defined above, 12.5 g.

(3) water, 2.5 g.

No gelation of the surfactant was observed. The ingredients are mixed to form homogeneous small granules. The granules were dried in a fluid bed dryer at 65 ° C for 15 minutes.

It can be calculated that the composition comprises 25% surfactant by dry weight. The glyphosate content was determined to be 66.2% ae

Example 15

For comparative greenhouse herbicidal effectiveness tests, aqueous concentrates containing 31% glyphosate ae as isopropylamine salt and 5.5% surfactant were prepared using a procedure similar to that used in Examples 1-4.

Compositions C1 and C2 were prepared using hitherto known tertiary alkylamines as surfactants. In C1 the surfactant is an ethoxylated alkylamine, a coconut fatty acid derivative having 5 moles EO. If the typical chemical structure of a tertiary etheramine of the invention is used for the C1 surfactant, it is seen that R1 is an alkyl group, derived from coconut oil fatty acid, with an average carbon chain length of about 12, m is 0, R3 is ethylene,

And x + y is 5. In C2 the surfactant is an ethoxylated alkylamine, a tallow fatty acid derivative, having 5 moles EO. If the typical chemical structure of a tertiary etheramine of the invention is used for the C2 surfactant, it will be seen that R1 is an alkyl group derived from a tallow fatty acid with an average carbon chain length of about 18, m is 0, R3 is an ethylene group, and x + y is 5.

Compositions E1-E9 were prepared using the tertiary and quaternary N-methyl etheramine surfactants of the invention. The chemical structures of these surfactants can be deduced from the following table, by reference to the typical structures shown above.

<td>Composition</td><td>Type</td><td>R1</td><td>R2</td><td>R3</td><td>m</td><td>x + y</td><td>AND</td>

<td>E1</td><td>tertiary</td><td>C12-14 alkyl</td><td>CH2CH (CHa)</td><td>CH2CH2</td><td> 2</td><td> 5</td><td></td>

<td>E2</td><td>tertiary</td><td>coco alkyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 10</td><td></td>

<td>E3</td><td>tertiary</td><td>isodecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 2</td><td></td>

<td>E4</td><td>tertiary</td><td>isodecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 5</td><td></td>

<td>E5</td><td>tertiary</td><td>isotridecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 2</td><td></td>

<td>E6</td><td>tertiary</td><td>isotridecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 5</td><td></td>

<td>E7</td><td>tertiary</td><td>C15 alkyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 2</td><td></td>

<td>E8</td><td>quaternary</td><td>isodecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 2</td><td>Cl-</td>

<td>E9</td><td>Quaternary</td><td>isotridecyl</td><td>CH2CH2CH2</td><td>CH2CH2</td><td> 1</td><td> 2</td><td>Cl-</td>

For greenhouse tests, seeds of velvetleaf (Abutilon theophrasti, ABUTH) and one-sided weed (Echinochloa crus-galli, ECHCF) were sown in 10.2 cm square pots with fertilizer added soil. Plants were allowed to grow until they reached the desired growth stage or size (3 leaf stage for ABUTH, 20-25 cm tall for ECHCF) by spraying. Before treatment, homogeneous pots were selected and four pots were assigned to each treatment, also for the no-spray control. Spray solutions were prepared by diluting the glyphosate concentrates in water. Spraying was accomplished with a device simulating agricultural field spraying equipment that produced a fine spray at a pressure of about 207 kilopascals. The speed of the sprayer travel over the plants to achieve the desired spray volume of 187 l / ha. For logistical reasons, all four replicates for each treatment were sprayed together. After spraying, the plants were returned to the greenhouse. Herbicidal efficacy was visually assessed 16 days after treatment and recorded as an estimated percent reduction on an arbitrary scale as compared to untreated plants. On this scale, 0 means no visible effect and 100 means all plants die. In the table below, the percentages of reduction are given as the mean of four replicates.

<td colspan="9">Percentage of reduction</td>

<td colspan="5">ABUTH</td><td colspan="4">ECHCF</td>

<td colspan="9">Composition</td>

PL 193 095 B1 cont. table

<td colspan="9">bd = no data available</td>

Example 16

To determine the compatibility of the surfactants of the invention with the highly concentrated aqueous glyphosate compositions, aqueous concentrates containing 480 g ae / L of glyphosate isopropylamine salt and 80 g / L surfactant were prepared using a procedure similar to Examples 1-4. Example 16 is approximately a third more concentrated (based on glyphosate ae) than Example 15.

Compositions C1 and C2 were prepared using hitherto known tertiary alkylamines as surfactants. The surfactant in C3 is the same as composition C1 of Example 15. The surfactant in C4 is the same as composition C2 of Example 15.

Compositions E10, E11, E12 and E13 were prepared using the same tertiary or quaternary N-methyl etheramine surfactants of the invention as are present in formulations E1, E6, E8 and E9 of Example 15, respectively.

Compatibility of the surfactant was determined by measuring the cloud point of the composition as shown in the table below.

Composition

C3

C4

E10

E11

E12

E13

Cloud point (° C)> 90> 90> 90> 90> 90> 90

Example 17

Compositions of the invention were prepared by a procedure similar to Examples 1-4 to illustrate the incorporation of a nonionic surfactant with an etheramine surfactant into a highly concentrated aqueous glyphosate composition. In compositions E14-E25, glyphosate is present as an isopropylamine salt at a concentration of 480 g ae / L, and the total surfactant concentration (etheramine plus nonionic surfactant) is 80 g / L. In all cases, the weight ratio of etheramine to nonionic surfactant is 4: 1.

The etheramine surfactant in formulation E14 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E14 is an ethoxylated C14-C16 linear primary alcohol having an average of 7 moles of EO.

The etheramine surfactant in formulation E15 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E15 is an ethoxylated C12-C13 linear primary alcohol having an average of 5 moles of EO.

The etheramine surfactant in formulation E16 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E16 is an ethoxylated C11 linear primary alcohol having an average of 7 moles EO.

The etheramine surfactant in formulation E17 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E17 is an ethoxylated C11-C12 linear primary alcohol having an average of 6 moles of EO.

PL 193 095 B1

The etheramine surfactant in formulation E18 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E18 is an ethoxylated secondary C12-C15 alcohol having an average of 9 moles of EO.

The etheramine surfactant in formulation E19 is the same as that in formulation E1 of Example 15. The nonionic surfactant in formulation E19 is an alkyl polyglucoside having a C8-C10 alkyl chain and an average of 1.7 moles of glucose.

The etheramine surfactant in formulation E20 is the same as that in formulation E6 of Example 15. The nonionic surfactant in formulation E20 is an ethoxylated C14-C16 linear primary alcohol having an average of 7 moles of EO.

The etheramine surfactant in formulation E21 is the same as that in formulation E6 of Example 15. The nonionic surfactant in formulation E21 is an ethoxylated C12-C15 secondary alcohol having an average of 9 moles of EO.

The etheramine surfactant in formulation E22 is the same as that in formulation E8 of Example 15. The nonionic surfactant in formulation E22 is an ethoxylated C14-C16 linear primary alcohol having an average of 7 moles of EO.

The etheramine surfactant in formulation E23 is the same as that in formulation E8 of Example 15. The nonionic surfactant in formulation E23 is an ethoxylated secondary C12-C15 alcohol having an average of 9 moles of EO.

The etheramine surfactant in formulation E24 is the same as that in formulation E9 of Example 15. The nonionic surfactant in formulation E24 is an ethoxylated C14-C16 linear primary alcohol having an average of 7 moles of EO.

The etheramine surfactant in formulation E25 is the same as that in formulation E9 of Example 15. The nonionic surfactant in formulation E25 is an ethoxylated C12-C15 secondary alcohol having an average of 9 moles EO.

Cloud points of compositions E14-E25 are shown in the table below.

Composition Cloud point (° C)

E14

E15

E16

E17

E18

E19

E20

E21

E22

E23

E24

E25> 90> 90> 90> 90> 90> 90> 90

Attempts have been made to prepare compositions similar to E14-E25, but containing instead of the etheramine component an ethoxylated tertiary alkylamine previously used as a surfactant. When an alkylamine, a coconut fatty acid derivative with 5 moles EO, or an alkylamine, a tallow fatty acid derivative with 5 moles EO, was used, the surfactant used so far has proved incompatible with any of the ethoxylated primary or secondary alcohol surfactants. - active used in compositions E14-E25, with equal contents of glyphosate, amine surfactant and nonionic surfactant as in the same compositions. Thus, a further unexpected advantage of the etheramine surfactants of the present invention over the alkylamine surfactants used heretofore is their relatively good compatibility with nonionic surfactants in highly concentrated aqueous glyphosate compositions.

The claims are to be interpreted as embracing all the features of the patentable novelty inherent in the present invention, including any features that may be regarded as equivalents by those skilled in the art to which the invention pertains.

Example 18

In addition to the composition of Example 15, aqueous concentrates containing 31% glyphosate ae as isopropylamine salt and 5.5% surfactant were prepared in a procedure similar to Examples 1-4.

Compositions C1 and C2 are as in Example 15.

Compositions C3 and C4 are similarly made using the tertiary alkylamine surfactants used heretofore. In C3 the surfactant is ethoxylated alkylamine, coconut fatty acid derivative having 2 moles EO. In C4 the surfactant is ethoxylated alkylamine, tallow fatty acid derivative having 2 moles EO.

Composition C5 was prepared using the heretofore used quaternary alkylamine surfactant, which is N-methylalkylammonium chloride, a coconut fatty acid derivative having 2 moles of EO.

Formulation C6 was prepared using the hitherto existing alkylamine oxide surfactant supplied by Tomah Products, Inc. as AO-728 Special. It is an alkylamine N-oxide having 2 moles EO; Tomah does not mention the chain length or the origin of the carbon chain.

Compositions E1-E9 are as in Example 15.

Composition E26 was prepared using etheramine oxide as the surfactant of the invention. Its chemical structure can be deduced from the following table by reference to the typical structures shown above.

<td>Composition</td><td>Type</td><td>Ri</td><td>R2</td><td>R3</td><td>m</td><td>x + y</td><td>AND</td>

<td>E26</td><td>N-oxide</td><td>isodecyl</td><td>CH2CH (CH3)</td><td>CH2CH2</td><td> 1</td><td> 2</td><td></td>

The greenhouse tests were carried out strictly as described in Example 15, except that herbicidal effectiveness was assessed 17 days after treatment. Average percentages of reduction are given in the table below.

<td colspan="9">Percentage of reduction</td>

<td></td><td></td><td colspan="2">ABUTH</td><td></td><td></td><td colspan="2">ECHCF</td><td></td>

<td colspan="9">Composition</td>

<td>Those</td><td> 33</td><td> 58</td><td> 69</td><td> 83</td><td> 41</td><td> 69</td><td> 66</td><td> 95</td>

PL 193 095 B1 cont. table

While illustrative embodiments of the invention have been described in detail, it should be understood that various other variations will be apparent to and readily made by those skilled in the art without departing from the spirit and scope of the invention. Accordingly, it is not intended that the scope of the claims appended hereto be limited to the examples and descriptions set forth herein above, but rather the claims are to be interpreted as including all patentable novelty inherent in the present invention, including any properties that are equivalent to it. can be treated by those skilled in the art to which the invention pertains.

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41929995	United States of America	A	1995-04-10
41929995	United States of America	A	1995-04-10
59936396	United States of America	A	1996-03-15
59936396	United States of America	A	1996-03-15
08599363	–	–	–
US19950419299	–	–	–
US19960599363	–	–	–

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ZA962816B	South Africa	B	1996-10-02
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WO9632839A2	World Intellectual Property Organization (WIPO)	A2	1996-10-24
AU5325196A	Australia	A	1996-11-07
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AR001582A1	Argentina	A1	1997-11-26
MX9707798A	Mexico	A	1997-12-31
EP0820231A2	European Patent Office (EPO)	A2	1998-01-28
PL322682A1	Poland	A1	1998-02-16
CZ332797A3	Czechia	A3	1998-02-18
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EP0820231B1	European Patent Office (EPO)	B1	1999-12-15
AT187602T	Austria	T	2000-01-15
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Glyphosate preparations containing etheroamine surfactants

Abstract

Term

PL 193 095 B1

PL 193 095 B1

C3

C4

E10

E11

E12

E13

PL 193 095 B1

E14

E15

E16

E17

E18

E19

E20

E21

E22

E23

E24

Priority claims7

Members50

Numbers

Titles2

Classification