Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
  • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
  • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

• the present invention relates to improved herbicidal glyphosate compositions comprising a glyphosate herbicide and surfactants.
• Glyphosate is a well known highly effective and commercially important non-selective systemic herbicide for combating a wide variety of unwanted vegetation, including agricultural weeds. Glyphosate is conventionally applied as a formulated product comprising the active ingredient and a surface active component, dissolved in water, to the foliage ofthe plants.
• glyphosate is formulated in commercial compositions in the form of a water-soluble salt.
• Salts in commercial use include the ammonium salt, alkylamine salts, such as the isopropylamine salt, alkali metal salts, such as the sodium salt, and the trimethylsulfonium salt.
• Monsanto' s well known commercial liquid formulation sold for years under the tradename Roundup ® comprises, per liter of formulated product, 360 g a.e. (acid equivalent) of glyphosate in the form of its isopropylamine salt and 180 g of a tallow amine ethoxylate surfactant .
• W095/33379 discloses trialkanolamine derivatives and quaternized derivatives thereof for enhancement of the efficacy of agricultural chemicals. It more particularly discloses compounds of the formula (R 5 -0) q -R 2
• Rl represents inter alia a linear or branched alkyl group or alkenyl group having 5 to 29 carbon atoms
• R 2 and R 3 may be the same or different and each represent hydrogen or a linear or branched alkyl or alkenyl group having from 5 to 29 carbon atoms
• p, q, and r may be the same or different and each represent a number of 1 to 30 in the average
• R 4 , R 5 and R 6 represent alkylene groups of 2 to 4 carbon atoms, for use with agricultural chemicals.
• Herbicidal compositions comprising glyphosate are" also disclosed.
• Example 1, Table 9 suggests herbicidal compositions comprising Roundup ® herbicide and a compound of the above formula wherein R x and R 2 are alkyl with 18
• R 3 is hydrogen, and p, q and r are each 5.
• W096/32839 discloses herbicidal glyphosate compositions comprising an effective herbicidal activity enhancing amount of a surfactant having the chemical formula
• R 3 -0 x -H / R 1 -(0-R 2 ) ra -N->0 ⁇ (R 3 -0) y -H
• x+y is in the range from 2 to 60
• R x is a straight or branched chain alkyl, aryl, or alkylaryl group having from 6 to 22 carbon atoms
• m is an average number from 1 to 10
• R 2 and R 3 in each of the m (0-R 2 ) or (R 3 -0) groups is independently alkylene with 1 to 4 carbon atoms.
• compositions may show very high glyphosate concentrations ranging from 450 to 500 g a.e./l while still showing an adequate surfactant concentration. Such compositions are said to show excellent herbicidal performance and a good storage stability under a wide range of temperatures.
• An aim of the present invention is to provide improved herbicidal glyphosate compositions.
• Another aim of the present invention consists in providing new glyphosate formulations which show an advantageous herbicidal activity together with an acceptable environmental profile.
• herbicidal compositions comprise
• R 3 -0) y -R 2 wherein R and R' represent hydrogen or alkyl having 1 to 3 carbon atoms, Rl and R2 each independently represent a straight or branched chain alkyl or alkenyl group having from 4 to 24 C-atoms, R 3 in each (R 3 -0) -group may be the same or different and represents alkylene having from 2 to 4 carbon atoms, A " is an agriculturally acceptable anion, and x and y are average numbers such that x+y is in the range from 2 to 160.
• compositions show a surprisingly high degree of herbicidal efficacy compared to prior art compositions, in the sense that, at typical glyphosate/surfactant ratios, the efficacy is at least similar to, but at increased glyphosate/surfactant ratios is drastically improved over, conventional surfactant (s) containing compositions.
• invention compositions show similar performance or biological effect to prior art compositions, with the advantage of using higher glyphosate/surfactant ratios. As a result, compositions of the invention may contain higher concentrations of glyphosate and be economically more interesting.
• glyphosate means N-phosphono- methylglycine in its acid form as well as in any salt form or derivative of glyphosate which in aqueous solution provides glyphosate anions along with suitable cation.
• Glyphosate includes the isopropylamine salt of glyphosate and other agriculturally acceptable salts of glyphosate such as those disclosed in US Patent 3,799,758.
• Surfactants as defined hereabove are known to the person skilled in the art and may be prepared by amnaonolysis of the corresponding alcohol (alkoxylated or not) with ammonia and a suitable catalyst. According to that method of preparation, the relevant alcohol or an alcohol mixture is heated in the presence of a suitable catalyst, such as for example a nickel catalyst, to a temperature ranging from 130 to 220 degrees C, preferably to about 190 degrees G, while flushing with nitrogen. Ammonia and hydrogen are then added continuously at a proportion of 5 to 1 to 1 to 2 by volume, preferably around 3 to 1.
• the pressure of the reaction medium can be varied from normal pressure to medium pressure conditions of approximately 20 bar. The resultant surfactant is obtained after 9 to 20 hours, after distillation of the reaction water.
• the product is cooled to room temperature, the catalyst is filtered off and the product is degassed in an evaporator.
• the product obtained may the further be reacted according to standard procedures in view of desirable alkoxylation, methylation, oxidation or quaternization.
• the weight ratio of glyphosate (expressed as glyphosate acid equivalent) to the total surface active component can vary over a considerable range, for example from 1:5 to 20:1.
• the optimum ratio will vary according to the manner and conditions in which the herbicidal composition is applied, the weed species to be treated, and the particular surfactant used, but is normally higher than 1:1, preferably higher than 2:1, more particularly higher than 5:1.
• Compositions of the invention are so advantageously effective that compositions with unexpectedly high glyphosate a. e . /surfactant ratios of the order of 20:1 or 15:1 still give good results .
• Compositions having a glyphosate a.e. to surfactant ratio of 8:1, 10:1 or 12:1 are particularly preferred.
• Such compositions show an acceptable commercial control of undesired plants similar to current commercial and prior art compositions while containing a reduced surfactant level.
• a composition of the invention can be a liquid concentrate intended to be diluted with water to form a spray solution for the herbicidal application.
• a liquid concentrate will normally contain at least 50 grams glyphosate acid equivalent per litre, and preferably at least 200 g/1, up to 600 g/1 bur in certain cases, more diluted ready to use formulations may contain glyphosate concentrations of about 2 to 20 g/1.
• Compositions containing 300 to 600 g/1 or 400 to 550 g/1 are preferred.
• a composition of the invention is a solid, for example a free-flowing particulate, granular solid or compressed into tablets or briquettes of any desired size and shape.
• Such compositions will usually contain not more than 5% and preferably not more than 1% by weight of water.
• Solid compositions may be formulated to include a water-soluble inert carrier, and for this purpose ammonium salts such as ammonium sulphate may be particularly suitable (see below) .
• the weight ratio of glyphosate (expressed as glyphosate acid equivalent) to surface active component in such compositions will be within the general range mentioned above.
• the amount of water-soluble inert carrier is not critical, and in the case of ammonium sulphate, the amount may, for example, range from 0% to 80% of the total weight of the composition.
• a dry composition normally contains at least 5 - 80 % w/w glyphosate acid equivalent.
• Solid compositions can be made, for example by spray drying an aqueous solution of the components, by dry-blending the ingredients in conventional granulating apparatus, or by extrusion blending whereby a granular product is obtained in an essentially single operation.
• Compositions of the invention also include spray solutions.
• the concentration of glyphosate is selected according to the volume per unit area of spray solution to be used and the desired rate of application of glyphosate per unit ' area.
• conventional spraying is done at 50-800 litres of spray solution per hectare, and the rate of application of gly- phosate is typically 0.125 to 4 kg of glyphosate acid equivalent per hectare.
• the rate of application of glyphosate per hectare will normally be within the same range, but the volume of spray solution per hectare will be considerably less, perhaps 15-50 litres per hectare. Spray solutions for controlled drop spraying are therefore more concentrated than those used in conventional spraying.
• Spray solution compositions can be prepared by diluting liquid concentrates or dissolving solid compositions of this invention as described above, or by tank mixing the separate components of the claimed compositions .
• Compositions of the invention may include a significant amount of an agriculturally-acceptable inorganic ammonium salt such as ammonium nitrate, ammonium thiocyanate, ammonium thiosulfate, ammonium phosphate, ammonium chloride, preferably ammonium sulphate, in addition to the glyphosate herbicide and surface active component.
• an agriculturally-acceptable inorganic ammonium salt such as ammonium nitrate, ammonium thiocyanate, ammonium thiosulfate, ammonium phosphate, ammonium chloride, preferably ammonium sulphate, in addition to the glyphosate herbicide and surface active component.
• compositions of the invention may further contain other adjuvants like formulation aids, such as extrusion aids, dyes, thickeners, defoamers, such as silicon based defoamers, stabilizers, anti-freeze agents such as ethylene glycol and other surfactants, or even other pesticidal actives, as may be determined by the person skilled in the art.
• formulation aids such as extrusion aids, dyes, thickeners, defoamers, such as silicon based defoamers, stabilizers, anti-freeze agents such as ethylene glycol and other surfactants, or even other pesticidal actives, as may be determined by the person skilled in the art.
• Rl and R2 each independently represent a straight or branched chain alkyl or alkenyl group having from 8 to 18 carbon atoms.
• Surfactants corresponding to formula (I) are preferred. Most preferred are surfactants of formula (I) wherein Rl and R2 each independently are a straight or branched chain alkyl or alkenyl group having 12 to 18 carbon atoms .
• x+y may range from 2 to 160 or even more while maintaining the good efficacy of the surfactant in the invention compositions.
• an alkoxylation degree of x+y comprised between 8 and 20, or 10 to 20 or preferably 12 to 20 has shown particularly advantageous.
• Another embodiment pertaining to the present invention includes an adjuvant for agricultural compositions, more particularly herbicidal glyphosate compositions, which comprises a surface active component as per formulae (I) to (III) •
• Adjuvant compositions of the invention similarly to the herbicidal compositions of the invention as described above can optionally contain other components .
• the concentrates and solutions of the invention may also be mixed with other pesticides.
• other pesticides Preferably though not required such other herbicides, insecticides or fungicides have low irritancy and toxicity.
• Yet another aspect of the present invention is a method of use of compositions described above for the control of unwanted vegetation.
• a solid composition (cmps 1) according to the invention was prepared as follows: A monium salt of glyphosate (MON8750 powder) , surfactant of formula C 12.18 H 25 _ 37 - (OCH 2 CH 2 ) 5 -NH- (CH 2 CH 2 0) 5 -C 12 . 18 H 25 . 37 (surfactant 1) and Rhodorsil 432 (tradename) antifoa were blended in that order at room temperature in a Hobart 5 planetary mixer. Water was then added and mixing continued until a dough is formed with a consistency suitable for extrusion. The dough mixture was charged into a Fuji Paudal EXDS-60 extruder fitted with a 0.7 mm radial screen. The extruded granules were dried using an
• Aeromatic Strea-1 fluid bed dryer controlled at approx 50 degrees C for approx 30 minutes, and sieved on an Endecotts EFL MK3 sieve shaker. Fines of ⁇ 0.3mm and oversize >2.0mm in size were removed by the sieving process and discarded. The final product was comprised of
• the product had an initial residual moisture content of ⁇ 1 % w/w.
• Example 1 was evaluated in a greenhouse test, in comparison with prior art compositions:
• a soluble liquid comprising 81.80% w/w isopropylamine salt of glyphosate (grade 205 - 46 %w/w of glyphosate acid equivalent) and 7.53 %w/w surfactant as per W096/32839 (having the amine structure wherein Rl is a branched alkyl chain having 11 - 14 C-atoms, R2 is isopropyl, m is 1, R3 is ethylene oxide and x+y is 5.
• the rates of application of this test were equivalent to 240, 480, 720 and 960 g a.e. /ha.
• Agropyron repens (AGRRE - narrow leaf) and
• Raphanus sativus (RAPSA - broadleaf) plants were grown from seed in 10 cm pots containing a natural sandy loam soil. The pots were placed in a growth-room until the spraying with a precise relative humidity as well as temperature control. After spraying plants were transferred to a greenhouse where light and temperature were also well controlled. Plants remained in this greenhouse for the remainder of the experiment. Both in growth-room and in the greenhouse, the water was supplied from below the pots by an automatic irrigation system.
• Glyphosate compositions were applied post- emergence with a precision laboratory sprayer (IMAG-DMLO) , delivering a volume of 200 1/ha solution through "Flat Even” nozzles (11003) in a single pass. All compositions were diluted in water. All replicate pots (4 pots per treatment) were sprayed with one pass of the sprayer.
• IMAG-DMLO precision laboratory sprayer
• Surfactant N.7 corresponds to a quaternized compound according to formula (II) wherein R is CH 3 , R' is CH 3 , R 3 is ethylene, x + y is 16, and R x is a saturated, linear alkyl chain from tallow.
• the tested compositions were tank mixed compositions comprising isopropylamine salt of glyphosate and the relevant surfactant in a ratio of 5:1.
• Glyphosate was applied at dose rates of 360, 720 and 1080 g a.e. /ha following essentially the procedure as detailed in Example 2.
• Plant species tested were Ely ⁇ nus repens (narrowleaf) , Raphanus sativus (broadleaf ) , Ipomea purpurea (broadleaf) .
• Phytotoxicity was evaluated and recorded at 6 , 18, and 25 days after treatment (DAT) .
• IPA-G means isopropyl amine salt of glyphosate
• sur means surfactant followed by the number of the surfactant as referred to earlier;
• 360, 720 and 1080 mean grams acid equivalent per hectare.
• a similar test was performed according to essentially the same protocol, except that evaluations were made as indicated (DAT) .
• compositions tested were as follows:
• composition b as defined in Example 2
• M composition c as defined in Example 2;
• H a tank mix comprising a 10/1 ratio of glyphosate isopropylamine salt and surfactant 1;
• ⁇ a tank mix comprising a 10/1 ratio of glyphosate isopropylamine salt and surfactant 3; ⁇ a tank mix comprising a 10/1 ratio of glyphosate isopropylamine salt and surfactant 4;
• a tank mix comprising a 10/1 ratio of glyphosate isopropylamine salt and surfactant 11.
• IPA-G means isopropylamine salt of glyphosate
• sur means surfactant followed by the surfactant number which refers to the corresponding surfactant definition
• 360, 720 and 1080 are the glyphosate acid equivalent dose rates applied, expressed in grams/ha.
• compositions of the invention perform unexpectedly well, and as good as prior art compositions with ratios of 5:1 or 2:1.
• the tested compositions were prior art compositions a, b and c, and tank mixed compositions comprising isopropylamine salt of glyphosate and the relevant surfactant in a ratio of 5:1.
• the surfactants used in this test are as follows :
• Glyphosate was applied at dose rates of 360, 720 and 1080 g a . e . /ha following essentially the procedure as detailed in Example 2.
• Plant species tested were Elymus repens (narrowleaf ) , Raphanus sativus (broadleaf) , Ipomea purpurea (broadleaf) .
• Phytotoxicity was evaluated and recorded at 6, 17, and 25 days after treatment (DAT) .
• IPA-G means isopropylamine salt of glyphosate
• sur means surfactant followed by the surfactant number which refers to the corresponding surfactant definition
• 360, 720 and 1080 are the glyphosate acid equivalent dose rates applied, expressed in grams/ha.
• compositions of the invention perform unexpectedly well compared to prior art compositions with ratios of 5:1 or 2:1.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Priority Applications (7)

Applications Claiming Priority (1)

Publications (1)

Family

ID=8164402

Family Applications (1)

Country Status (7)

Cited By (1)

Families Citing this family (2)

Citations (8)

Family Cites Families (2)

• 2001
  • 2001-05-08 JP JP2002586735A patent/JP2004527565A/ja active Pending
  • 2001-05-08 AU AU2001256335A patent/AU2001256335B2/en not_active Ceased
  • 2001-05-08 WO PCT/EP2001/005022 patent/WO2002089585A1/en not_active Ceased
  • 2001-05-08 CA CA002446694A patent/CA2446694A1/en not_active Abandoned
  • 2001-05-08 US US10/477,252 patent/US20040198606A1/en not_active Abandoned
  • 2001-05-08 MX MXPA03010265A patent/MXPA03010265A/es not_active Application Discontinuation
  • 2001-05-08 BR BRPI0117035A patent/BRPI0117035A2/pt not_active IP Right Cessation

Patent Citations (8)

Also Published As

Similar Documents

Legal Events