WO2011070051A2 - Formulations de concentré de suspension liquide contenant du saflufénacil - Google Patents

Formulations de concentré de suspension liquide contenant du saflufénacil Download PDF

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WO2011070051A2
WO2011070051A2 PCT/EP2010/069133 EP2010069133W WO2011070051A2 WO 2011070051 A2 WO2011070051 A2 WO 2011070051A2 EP 2010069133 W EP2010069133 W EP 2010069133W WO 2011070051 A2 WO2011070051 A2 WO 2011070051A2
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WIPO (PCT)
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suspension concentrate
liquid suspension
weight
concentrate formulation
formulation according
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PCT/EP2010/069133
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English (en)
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WO2011070051A3 (fr
Inventor
Klaus Kolb
Wolfgang Gregori
Bernd Sievernich
Michael Krapp
Jörg STEUERWALD
Heidi Emilia Saxell
Steven Bowe
Rex Liebl
Terrance M. Cannan
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Basf Se
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Application filed by Basf Se filed Critical Basf Se
Priority to AU2010329961A priority Critical patent/AU2010329961B2/en
Priority to CN201080055652.5A priority patent/CN102655748B/zh
Priority to BR112012013151-6A priority patent/BR112012013151B1/pt
Priority to US13/512,623 priority patent/US8703650B2/en
Priority to CA2782759A priority patent/CA2782759C/fr
Publication of WO2011070051A2 publication Critical patent/WO2011070051A2/fr
Publication of WO2011070051A3 publication Critical patent/WO2011070051A3/fr

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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to new liquid suspension concentrate formulations of 2- chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 -(2H)pyrimidinyl]-4-fluoro- N-[[methyl(1 -methylethyl)amino]sulfonyl]benzamide, herein after also referred to with its common name "saflufenacil".
  • the invention also relates to the use of the
  • herbicide compounds may be formulated in solid forms, such as wettable powders and wettable granules (WG), as well as in liquid forms, such as emulsifiable concentrates (ECs), aqueous suspension concentrates (SCs) or oil based suspension concentrates (ODs).
  • ECs emulsifiable concentrates
  • SCs aqueous suspension concentrates
  • ODs oil based suspension concentrates
  • salfufenacil is only sparingly soluble in water and mixtures of water with water-miscible solvents such as Ci-C4-alkanols or C2-C4-alkandiols and -triols.
  • Oil suspension concentrate (OD) formulations contain an active ingredient (a.i.) in the form of finely divided solid particles, which are suspended (dispersed) in a water- immiscible dispersing fluid such as hydrocarbon solvents or fatty acid esters, wherein the active ingredient is usually insoluble or only sparingly soluble (less than 2000 ppm).
  • the dispersing fluid may however include further active ingredients in dissolved form.
  • Suspension concentrates usually utilize surface-active compounds (surfactants), such as dispersants and emulsifying agents for stabilizing the a.i.
  • formulations may be difficult to handle and the bioefficacy may be inconsistent.
  • Saflufenacil having the following formula I is an herbicidal active substance which has been disclosed in WO 01/083459. Further processes for its preparation are described in WO 03/097589, WO 05/054208, WO 06/097589 and WO 06/125746. A crystalline and essentially solvent-free form of saflufenacil, herein after also referred to as the crystalline anhydrate form, is disclosed in WO 08/043835.
  • saflufenacil When trying to prepare aqueous concentrate formulations of saflufenacil one faces several problems. Due to its N-(aminosulfonyl)-carboxamide side-chain saflufenacil is susceptible to hydrolysis at basic pH values and elevated temperatures. In aqueous media the modifications of saflufenacil, namely crystalline hydrates, a crystalline anhydrate and amorphous forms, may undergo uncontrolled interconversion, which in turn may lead to coarsening of the saflufenacil particles, in particular in aqueous suspension concentrate formulations. These factors might result in a reduced chemical and physical stability of the formulations, especially when stored over prolonged periods of time and/or at elevated temperatures. Said factors may also lead to poor dilution properties as the coarse saflufenacil particles are prone to separate from the diluted formulation.
  • saflufenacil as an oil based suspension concentrate (OD).
  • OD formulations containing high concentrations of the active ingredients pose the difficulty of dispersing large amounts of saflufenacil particles in the dispersing fluid.
  • stability problems in particular upon storage over prolonged periods and/or at elevated temperatures, often have to be overcome.
  • WO 01/83459 discloses uracil substituted phenyl sulfamoyl carboxamides having herbicidal activity. Also disclosed are different formulation types including oily dispersions. However, WO 01/83459 does not describe liquid suspension concentrate formulations containing saflufenacil that are stable over extended storage periods while maintaining good applicability and high herbicidal activity. Up to now, saflufenacil is available in the form of wettable granule formulations and as emulsion concentrate formulations with low a.i. loading. A liquid suspension
  • liquid suspension concentrate formulations of saflufenacil that exhibit high physical and chemical stability over prolonged storage periods while maintaining its biological efficacy. Upon dilution with water the formulations should give stable aqueous compositions of saflufenacil that do not show formation of sediments and have a high herbicidal activity.
  • this object could be achieved by formulating the crystalline anhydrate of saflufenacil together with a diluent selected from esters and amides of fatty acids and hydrocarbon solvents, two different non-ionic surfactants each having a polyalkoxylate moiety and an alkylarene sulfonate as anionic surfactant.
  • Saflufenacil is present in the formulation in the form of suspended particles.
  • the present invention relates to a liquid suspension concentrate formulation for plant protection, comprising the components:
  • At least two different non-ionic surfactants selected from poly-ethoxylate-co-C3-C4- alkoxylates of C3-C2o-alkanols, polyethoxylates of C8-C22-alkanols, polyester- polyoxyethylene block copolymers, polyethoxylates of mono-, di- or tristyryl phenols and polyethoxylates of vegetable oils; and
  • At least one anionic surfactant selected from Ci-Ci6-alkylarene sulfonates.
  • the present invention entails a series of advantages.
  • the formulations according to the invention exhibit good physical and chemical stability over prolonged storage times.
  • the formulations of the invention show outstanding herbicidal activity in particular against broadleaf weed species that have high economical impact.
  • Cs-C26-fatty acid refers to a fatty acid having from 8 to 26 carbon atoms.
  • Cs-C26-fatty acids are the saturated fatty acids caprylic acid, caprinic acid, lauric acid, myristic acid, palmitic acid, margaric acid, stearic acid, arachidic acid, behenic acid, lignoceric acid and cerotic acid; the mono-unsaturated fatty acids undecylenic acid, palmitoleic acid, oleic acid, elaidic acid, vaccenic acid, eicosenic acid, cetoleic acid, erucic acid and nervonic acid; and the poly-unsaturated fatty acids linoleic acid, a-linolenic acid, ⁇ -linolenic acid, arachidonic acid, timnodonic acid, clupanodonic acid and cervonic acid.
  • mono- and di-Ci-C4-alkyl amide of a Cs-C26-fatty acid refer to an amide of a C8-C26-fatty acid, as defined herein, that is N-substituted with one and two, respectively, alkyl group(s) having from 1 to 4 carbon atoms.
  • Examples for mono-Ci- C 4 -alkyl amides of Cs-C26-fatty acids are the mono-methyl amides, mono-ethyl amides, mono-propyl amides, mono-isopropyl amides, mono-butyl amides and mono-isobutyl amides of the aforementioned fatty acids.
  • di-Ci-C 4 -alkyl amides of Cs- C26-fatty acids are the di-methyl amides, di-ethyl amides, di-propyl amides, di-isopropyl amides, di-butyl amides, di-isobutyl amides, methyl-ethyl amides, methyl-propyl amides, methyl-isobutyl amides, methyl-tert-butyl amides, ethyl-propyl amides, ethyl- isopropyl amides, ethyl-butyl amides, ethyl-isobutyl amides, propyl-isopropyl amides, propyl-butyl amides and propyl-isobutyl amides of the aforementioned fatty acids.
  • Ci-Cs-alkyl ester of a Cs-C26-fatty acid refers to a Cs-C26-fatty acid, as defined herein, that is esterified with an alkanol having from 1 to 8 carbon atoms.
  • Ci-Cs-alkyl esters of Cs-C26-fatty acids are the methyl esters, ethyl esters, propyl esters, isopropyl esters, butyl esters, isobutyl esters, tert-butyl esters, 1 -methyl- propyl esters, pentyl esters, 1 -methyl-butyl esters, 2-methyl-butyl esters, 3-methyl-butyl esters, hexyl esters, 1 -methyl-pentyl esters, 2-methyl-pentyl esters, 1 -ethyl-butyl esters, 1 ,2, -dimethyl-butyl esters, heptyl esters, 1 -methyl-hexyl esters, 2-methyl-hexyl esters, 3-methyl-hexyl esters, 4-methyl-hexyl esters, 5-methyl-hexyl esters, 1 -ethyl- pentyl esters,
  • C 4 -Ci5-dialkyl dicarboxylic acid ester refers to a diester of an alkyl dicarboxylic acid with two different or identical alkanols, wherein said diester has from 4 to 15 carbon atoms.
  • C 4 -Ci5-dialkyl dicarboxylic acid esters are dimethyl oxalate, ethyl methyl oxalate, diethyl oxalate, ethyl propyl oxalate, ethyl isopropyl oxalate, dipropyl oxalate, propyl isopropyl oxalate, ethyl butyl oxalate, methyl pentyl oxalate, propyl butyl oxalate, dibutyl oxalate, butyl pentyl oxalate, dipentyl oxalate, butyl hexyl oxalate, dimethyl malonate, methyl ethyl malonate, diethyl malonate, propyl ethyl malonate, isopropyl ethyl malonate, methyl propyl malonate, methyl iso
  • N-Cs-C-is-alkyl pyrrolidone refers to a N-alkylated derivative of pyrrolidone having from 5 to 15 carbon atoms.
  • Examples of N-Cs-C-is-alkyl pyrrolidone are N-methyl pyrrolidone, N-ethyl pyrrolidone, N-propyl pyrrolidone, N-isopropyl pyrrolidone, N-butyl pyrrolidone, N-isobutyl pyrrolidone, N-pentyl pyrrolidone, N-hexyl pyrrolidone, N-(4-ethyl-pentyl) pyrrolidone, N-octyl pyrrolidone, N-nonyl pyrrolidone, N- decyl pyrrolidone and N-(7-methyl-decyl) pyrrolidone.
  • C2-C6-lactone refers to an internal cyclic ester of a hydroxylated alkanoic acid having from 2 to 6 carbon atoms.
  • An example for a C2-C6-lactone is ⁇ - butyrolactone.
  • C3-C4-alkylene oxide refers to an epoxide ring wherein the carbon atoms of the epoxide ring is substituted with one or two methyl groups or with one ethyl group.
  • C3-C4-alkylene oxide refers to propylene oxide, 1 ,2-butylene oxide, cis- or trans- 2,3-butylene oxide and/or isobutylene oxide.
  • concentrate formulation refers to a pesticidal formulation that contains at least 10 % by weight, preferably at least 15 % by weight and in particular at least 25 % by weight, based on the total weight of the formulation, of active ingredients.
  • substituted ammonium refers to an ammonium counter ion of a salt, wherein 1 , 2, 3, or 4 hydrogen atoms of the ammonium ion are replaced with C1-C6- alkyl radicals which are unsubstituted or substituted with halogen, CN, OH, optionally substituted Ci-C6-alkoxy and/or optionally substituted aryl.
  • substituted ammonium examples include methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2- hydroxyethoxy)-eth-1 -ylammonium, di-(2-hydroxyeth-1 -yl) ammonium,
  • the crystalline anhydrate form of saflufenacil employed in the formulation of the invention refers to the saflufenacil modification that is disclosed in WO 08/043835. Accordingly, the crystalline anhydrate form is an essentially solvent- free crystalline form of saflufenacil (compound of formula I), herein also referred to as saflufenacil anhydrate.
  • essentially solvent-free means that the crystalline anhydrate form comprises no detectable amounts of solvents incorporated into the crystal lattice, i.e. the amount of solvent in the crystal lattice is less than 10 mol%, in particular not more than 5 mol%, based on saflufenacil.
  • the crystalline anhydrate form can be identified by means of X-ray powder
  • an X-ray powder diffractogram recorded at 25°C using Cu- ⁇ radiation (1 .54178 A) shows at least 2, as a rule at least 4, frequently at least 6, in particular at least 8 and specifically all of the reflexes detailed in Table 1 hereinbelow as 29values, or as interplanar spacings d:
  • Table 2 Crystallographic characteristics of the crystalline anhydrate form (measured at
  • differential scanning calorimetry can also be employed for identifying the anhydrate form.
  • the anhydrate form shows a thermogram with a characteristic melting peak in the range between 170 and 200°C.
  • the peak maximum is typically in the range of approximately 180°C to 190°C.
  • the melting points indicated herein refer to data determined by means of DSC, crucible material aluminum, heating rate 5 K/min).
  • the crystalline saflufenacil anhydrate may be prepared by controlled crystallization from a solution of saflufenacil in an organic solvent which is essentially free from water as described in WO 08/043835.
  • the saflufenacil anhydrate is present predominantly in the form of finely divided solid particles which are suspended in the organic diluent.
  • the formulations of the invention are therefore also referred to as oil suspension concentrates. They can also comprise a small amount of saflufenacil anhydrate in dissolved form.
  • the amount of dissolved active saflufenacil anhydrate will, as a rule, not exceed 20% by weight, in particular 10% by weight, based on the total amount of the saflufenacil anhydrate which is present in the formulation.
  • the particle size of the suspended particles is in the range which is typical of oil suspension concentrates.
  • the particles have a mean particle diameter, herein also termed D 5 o value, in the range from 0.5 to 20 ⁇ , in particular in the range from 0.8 to 10 ⁇ .
  • the D 5 o-value is defined as the value that is above the diameters of 50% by weight of the particles and below the diameters of 50% by weight of the particles.
  • At least 80% by weight, in particular at least 90% by weight, of the particles have particle sizes in the stated ranges.
  • a particle size that is not exceeded by the diameters of at least 90% by weight of the particles is herein also termed the Dgo-value.
  • the Dgo-value of the suspended a.i. particles of the formulation according to the invention will not exceed 20 ⁇ , preferably not exceed 10 ⁇ and in particular not exceed 5 ⁇ .
  • at least 40% by weight, preferably at least 60% by weight and in particular at least 80% by weight of the particles have a particle diameter of below 8 ⁇ or even below 5 ⁇ .
  • the particle size of the saflufenacil anhydrate particles can be determined by conventional methods such as light-scattering.
  • the particles of saflufenacil anhydrate (component a)) contained in the formulation of the invention are solid a.i. particles, i.e. the particles mainly contain pure component a).
  • the purity of the component a) is usually at least 90% by weight, preferably at least 95% and in particular at least 97% by weight.
  • the concentration of component a) in the formulation of the invention is typically in the range of from 0.5 to 50% by weight, in particular in the range of from 1 to 40% by weight, and specifically in the range of from 1 to 30% by weight, based on the total weight of the formulation.
  • the at least one diluent b) contained in the formulations according to the invention is selected among, as diluents b1 ), hydrocarbon solvents having a boiling point of at least 100°C, and, as diluents b2), Ci-Cs-alkyl esters of Cs-C26-fatty acids and mono- and di- Ci-C4-alkyl amides of Cs-C26-fatty acids, and mixtures thereof.
  • those solvents and solvent mixtures are preferred which are liquid under standard conditions.
  • liquid means that the diluent has, under standard conditions, a dynamic viscosity at 20°C of, as a rule, no more than 150 mPa.s, in particular no more than 100 mPa.s, specifically no more than 50 mPa.s, in particular in the range of from 1 to 150 mPa.s, preferably in the range of from 2 to 100 mPa.s and in particular in the range of from 3 to 50 mPa.s (determined as specified in ASTM D 445).
  • Diluents b1 ) of the formulations according to the present invention are preferably chosen from aliphatic hydrocarbon solvents and aromatic hydrocarbon solvents which all have boiling points of at least 100°C and preferably boiling points in the range of from 150 to 310°C (as general reference for hydrocarbons see, for example, Rompp Lexikon Chemie, 10th edition, volume 3, page 2202 (1997), Georg Thieme Verlag Stuttgart / New York).
  • aliphatic hydrocarbon solvents with a boiling point of at least 100°C particularly refer to saturated and unsaturated hydrocarbons that may optionally include a non-aromatic carbocycle, such as linear, branched and cyclic alkanes and alkenes, that have boiling points in the stated range and include 7 to about 18 carbon atoms, and in particular also to mixtures of these aliphatic hydrocarbons.
  • a non-aromatic carbocycle such as linear, branched and cyclic alkanes and alkenes
  • Exxsol denotes products that predominantly contain kerosene having been depleted of aromatic components, such as ExxsolTM D30, ExxsolTM D40, ExxsolTM D80, ExxsolTM D100, ExxsolTM D120 and ExxsolTM D220/230.
  • An example of an aliphatic hydrocarbon having a carbocycle is limonene.
  • aromatic hydrocarbon solvents with a boiling point of at least 100°C particularly refer to mono- or polycyclic aromatic compounds which optionally may carry one or more aliphatic or araliphatic substituents, in particular alkyl and arylalkyi moieties, and which have boiling points in the stated range.
  • Said aromatic hydrocarbon solvents preferably refer to mixtures of such aromatic compounds that are obtained by distillation in particular from crude oil products as fractions in the given boiling point range, such as the commercial products known under the trade names Solvesso ® , in particular Solvesso ® 100, Solvesso ® 150, Solvesso ® 200, Solvesso ® 150 ND and Solvesso ® 200 ND, Aromatic ® , in particular Aromatic ® 150 and Aromatic ® 200, Hydrosol ® , in particular Hydrosol ® A 200 and Hydrosol ® A 230/270, Caromax ® , in particular Caromax ® 20 and Caromax ® 28, Aromat K 150, Aromat K 200, Shellsol ® , in particular Shellsol ® A 100 and Shellsol ® A 150, and Fin FAS-TX, in particular Fin FAS- TX 150 und Fin FAS-TX 200.
  • Solvesso ® in particular Solvesso ® 100, Solvesso ® 150,
  • Solvesso ® 150 ND mainly contains aromatic hydrocarbons having 10 or 1 1 carbon atoms which boil in the range of from 175 to 209°C and primarily consist of alkylbenzenes
  • Solvesso ® 200 ND mainly contains aromatic hydrocarbons having 10 to 14 carbon atoms which boil in the range of from 235 to 305°C and primarily consist of alkylnaphthalenes.
  • aromatic hydrocarbon solvents is a product known under its tradename Hisol SAS-296 that consists of a mixture of 1 -phenyl-1 -xylylethane and 1 - phenyl-1 -ethylphenylethane.
  • Preferred diluents b2) are the Ci-C4-alkyl esters of Ci2-C22-fatty acids, in particular the methyl esters of saturated or mono-unsaturated Ci4-Cis-fatty acids, and mono- or di- Ci-C3-alkyl amides of Ci2-C22-fatty acids, in particular the mono-methyl amides, mono- ethyl amides, di-methyl amides and di-ethyl amides of saturated or mono-unsaturated Ci4-i8-fatty acids.
  • a mixture of methyl esters of saturated and mono-unsaturated Cu- Ci8-fatty acids is commercially available e.g. under the trade name SynativeTM ES ME Tl 05 (Cognis).
  • the at least one diluent b) is either selected from diluents b1 ) or selected from diluents b2), in particular from those mentioned herein as preferred.
  • the component b) is a mixture of at least one diluent b1 ) and at least one diluent b2).
  • the component b) comprises at least one methyl ester of a saturated or mono-unsaturated Ci4-Cis-fatty acid.
  • the total amount of diluents b) will, as a rule, not exceed 90% by weight, in particular 80% by weight, based on the total weight of the formulation according to the invention and is typically in the range from 25 to 90% by weight, in particular in the range from 35 to 85% by weight and specifically in the range of from 40 to 80% by weight, based on the total weight of the formulation according to the invention.
  • the formulations of the present invention may optionally further contain at least one liquid diluent e) that differs from diluents b) and is an organic solvent having at least one oxygen atom.
  • Diluents e) may be selected from Ci-Ci2-alcohols, including alcohols having at least one ether group or at least one keto group, C3-Ci6-esters other than those of component b), including diesters and C2-C6-lactones, amides other than those of component b), ethers, ketons, aldehydes, N-alkyl-Cs-Cs-lactams, N,N'-dimethyl-C3- C5-alkylene ureas, C2-C4-alkylene carbonates, tri-Ci-C4-alkyl phosphates, DMSO and the like.
  • Ci-Ci2-alcohols including alcohols having at least one ether group or at least one keto group, C3-Ci6-esters other than those of component b), including diesters and C2-C6-lactones, amides other than those of component b), ethers, ketons, aldehydes, N
  • Preferred diluents e) are selected from C4-Cis-dialkyl dicarboxylic acid esters, in particular dimethyl and diethyl C3-Cio-dicarboxylic acid esters, N-Cs-ds-alkyl pyrrolidones, in particular N-Cs-Cs-alkyl pyrrolidones, Cs-Cs-lactones, in particular ⁇ - butyrolactone, C3-Ci2-alkanols, in particular Cs-alkanols, and DMSO.
  • C4-Cis-dialkyl dicarboxylic acid esters in particular dimethyl and diethyl C3-Cio-dicarboxylic acid esters
  • N-Cs-ds-alkyl pyrrolidones in particular N-Cs-Cs-alkyl pyrrolidones
  • Cs-Cs-lactones in particular ⁇ - butyrolactone
  • the total amount of diluents e), if present, is preferably in the range from 0.5 to 35% by weight, in particular from 1 to 25% by weight, more preferably from 5 to 20% by weight, based on the total weight of the formulation.
  • the formulations of the invention also include, as component c), at least two different non-ionic surfactants that each comprises a polyalkoxylate moiety, such as in particular an ethylene oxide polymer moiety or an ethylene oxide/C3-C4-alkylene oxide block copolymer moiety.
  • Non-ionic surfactants c) are preferably selected from the surfactant groups c1 ), c2), c3), c4), c5), c6) and c7) as defined herein below.
  • polyalkoxylate and polyalkoxylated used herein refer to polyether radicals derived from alkylene oxide, in particular C2-C 4 -alkylene oxide, such as ethylene oxide and C3-C 4 -alkylene oxide.
  • polyethoxylate and polyethoxylated used herein refer to polyether radicals derived from ethylene oxide.
  • poly-ethoxy-co-C3-C 4 -alkoxylate and poly-ethoxy-co-C3-C 4 -alkoxylated refer to a polyether radical derived from a mixture of ethylene oxide and C3-C 4 -alkylene oxide.
  • poly-ethoxy-co-propoxylate and poly-ethoxy-co-propoxylated refer to a polyether radical derived from a mixture of ethylene oxide and propylene oxide.
  • polyethoxylates have repeating units of the formula [CH2CH2O] while poly-ethoxy- co-propoxylates have repeating units of the formulae [CH2CH2O] and [CH(CH3)CH20].
  • the number of such repeating units will generally range from 2 to 200, in particular from 3 to 100, especially from 3 to 50.
  • the non-ionic surfactants of group c1 are selected from poly-ethoxylate-co-C3-C 4 - alkoxylates of linear or branched C3-C2o-alkanols, such as poly-ethoxy-co-propoxylated Cs-C2o-fatty alcohols or poly-ethoxy-co-propoxylated C3-C2o-oxoalcohols.
  • non-ionic surfactants c1 are poly-ethoxylate-co-propoxylates of octanol, poly- ethoxylate-co-propoxylates of 2-ethyl-hexanol, poly-ethoxylate-co-propoxylates of nonanol, poly-ethoxylate-co-propoxylates of 3-propyl-heptanol, poly-ethoxylate-co- propoxylates of 2-ethyl-octanol, poly-ethoxylate-co-propoxylates of butanol, poly- ethoxylate-co-propoxylates of iso-butanol, and poly-ethoxylate-co-propoxylates of decanol.
  • Preferred non-ionic surfactants c1 ) are poly-ethoxylate-co-propoxylates of C3- Cs-alkanols and particularly preferred are poly-ethoxylate-co-propoxylates of C3-C6- alkanols.
  • the non-ionic surfactants of the group c1 ) described herein is commercially available e.g. under the trade name AtlasTM G 5000 (Croda).
  • the non-ionic surfactants of group c2) are selected from polyethoxylates of linear or branched C8-C22-alkanols, such as polyethoxylated Cs-C22-fatty alcohols and polyethoxylated C8-C2o-oxoalcohols. Examples of non-ionic surfactants e1 ) are
  • polyethoxylated octanol polyethoxylated 2-ethyl-hexanol, polyethoxylated nonanol, polyethoxylated decanol, polyethoxylated 3-propyl-heptanol, polyethoxylated 2-ethyl- octanol, polyethoxylated lauryl alcohol, polyethoxylated isotridecanol and
  • non-ionic surfactants c2) are polyethoxylates of C8-Ci6-alkanols and particularly preferred are polyethoxylates of Cio-Ci3-alkanols.
  • the non-ionic surfactants of the group c2) described herein are commercially available e.g. under the trade names Lutensol ® ON (BASF), Lutensol ® AO (BASF) and Lutensol ® TO (BASF).
  • the non-ionic surfactants of group c3) are selected from polyester-polyoxyethylene block copolymers of the type ABA, where blocks A are self-condensation products of hydroxylated Cs-C24-fatty acids and blocks B are polyoxyethylene moieties. Blocks A and B of preferred non-ionic surfactants c3) both have molecular weights that exceed 500 grams per mol.
  • the non-ionic surfactants of group c3) are known e.g. from EP 0000424 and are typically prepared by reacting hydroxyl-C8-C24-fatty acid condensate with polyoxyethylene (often also referred to as poly(ethylene oxide)).
  • Particularly preferred non-ionic surfactants c3) have blocks A consisting of condensed 12- hydroxystearic acid and are commercially available e.g. under the tradename
  • the non-ionic surfactants of group c4) are selected from polyethoxylates of mono-, di- or tristyryl phenols, in particular from polyethoxylates of tristyryl phenols, specifically from polyethoxylates of 2,4,6-tristyryl phenols.
  • the non-ionic surfactants c4) are commercially available e.g. under the tradename Soprophor BSU (Rhodia).
  • the non-ionic surfactants of group c5) are selected from fatty acid polyalkoxylates and triglyceride polyalkoxylates, such as the Serdox ® NOG products (Condea), from polyalkoxylated animal fats, such as lard, tallow, milkfat, cod liver oil and whale oil, and from polyalkoxylated vegetable oils, such as soya oil, rapeseed oil, corn oil, sunflower oil, cotton seed oil, linseed oil, coconut oil, palm oil, safflower oil, walnut oil, peanut oil, olive oil or castor oil.
  • Preferred non-ionic surfactants c5) are polyalkoxylated and in particular polyethoxylated vegetable oils, in particular rapeseed oil and castor oil.
  • Non-ionic surfactants of group c6) are selected from non-ionic block copolymers comprising at least one poly(ethylene oxide) moiety PEO and at least one polyether moiety PAO derived from C3-C4-alkylene oxides.
  • the at least one PAO moiety of a non-ionic block copolymer c6) usually comprises at least 3, preferably at least 5, in particular 10 to 100 repeating units (number average) which are derived from C3-C4 alkylene oxides, such as propylene oxide, 1 ,2-butylene oxide, cis- or trans-2,3-butylene oxide or isobutylene oxide.
  • the PAO moieties comprise at least 50 % by weight, and more preferably at least 80 % by weight of repeating units derived from propylene oxide.
  • the at least one PEO moiety of a non-ionic block copolymer c6) usually comprise at least 3, preferably at least 5, and more preferably at least 10 repeating units derived from ethylene oxide (number average).
  • the weight ratio of PEO moieties and PAO moieties usually ranges from 1 :10 to 10:1 , preferably from 2:8 to 7:3 and in particular from 3:7 to 6:4.
  • Suitable non-ionic surfactants c6) are described e.g. in WO 06/002984, in particular those having the formulae P1 to P5 given therein.
  • Preferred non-ionic surfactants c6) are selected from ethylene oxide/propylene oxide block copolymers, in particular those that have the aforementioned preferred properties.
  • the non-ionic surfactants c6) are commercially available e.g. under the trade names Pluronic ® (BASF), such as Pluronic ® PE and Pluronic ® RPE.
  • the non-ionic surfactants of group c7) are selected from polyethoxylates of polyol esters, wherein the polyols may be partially or completely esterified with saturated or unsaturated C6-C22-alkanoic acids, such as mono-, di- and triesters of glycerine and mono-, di-, tri-, tetra-, penta- and hexaesters of sorbitol, e.g. glycerine monostearate, sorbitol monooleat and sorbitol hexaoleat.
  • saturated or unsaturated C6-C22-alkanoic acids such as mono-, di- and triesters of glycerine and mono-, di-, tri-, tetra-, penta- and hexaesters of sorbitol, e.g. glycerine monostearate, sorbitol monooleat and sorbitol hexa
  • Preferred non-ionic surfactants c7) are polyethoxylates of esters of sorbitol with C6-C22-alkanoic acids, in particular preferred are polyethoxylates of sorbitol hexaoleate.
  • the non-ionic surfactants of the group c7) described herein are commercially available e.g. under the trade name AtlasTM G 1086 (Croda).
  • non-ionic surfactants c) are selected from surfactants of groups c1 ), c2), c3), c4) and c5), even more preferred non-ionic surfactants c) are selected from surfactants of groups c1 ), c2), c3) and c5), specifically from those surfactants of groups c1 ), c2), c3) and c5) mentioned herein as preferred.
  • the component c) comprises a non-ionic surfactant c2), in particular a polyethoxylate of a C8-Ci6-alkanol, and a non- ionic surfactant c5), in particular a polyethoxylate of a vegetable oil.
  • the component c) comprises a non-ionic surfactant c1 ), in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol, and a non-ionic surfactant c3), in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer.
  • the component c) comprises a non-ionic surfactant c1 ), in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol, and a non-ionic surfactant c3), in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer, and in addition a non-ionic surfactant c2), in particular a polyethoxylate of a C8-Ci6-alkanol.
  • a non-ionic surfactant c1 in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol
  • a non-ionic surfactant c3 in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer
  • a non-ionic surfactant c2 in particular a polyethoxylate of a C8-Ci6-alkanol.
  • the component c) comprises a non-ionic surfactant c1 ), in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol, and a non-ionic surfactant c3), in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer, and in addition a non-ionic surfactant c4), in particular a polyethoxylate of a tristyryl phenol.
  • a non-ionic surfactant c1 in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol
  • a non-ionic surfactant c3 in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer
  • a non-ionic surfactant c4 in particular a polyethoxylate of a tristyryl phenol.
  • the component c) comprises a non-ionic surfactant c2), in particular a polyethoxylate of a Cs-Ci6- alkanol, and a non-ionic surfactant c5), in particular a polyethoxylate of a vegetable oil
  • the component b) comprises a diluent b2), in particular a Ci-C4-alkyl ester of a C12- C22-fatty acid.
  • the component c) comprises a non-ionic surfactant c1 ), in particular poly-ethoxylate-co-propoxylate of a Cs-Cs-alkanol, and a non-ionic surfactant c3), in particular a poly(hydroxy fatty acid)- polyoxyethylene block copolymer, and the component b) comprises a diluent b1 ), which is preferably selected from diluents b1 ) having boiling points in the range of from 150 to 310°C.
  • the total amount of non-ionic surfactants c) will, as a rule, not exceed 50% by weight, in particular 40% by weight, based on the total weight of the formulation according to the invention and is typically in the range from 1 to 50% by weight, in particular in the range from 3 to 40% by weight and specifically in the range of from 5 to 35% by weight, based on the total weight of the formulation according to the invention.
  • the formulations of the invention also include, as component d), at least one anionic surfactant that is selected from Ci-Ci6-alkylarene sulfonates, such as mono-, di- and tri- Ci-Ci6-alkylbenzene sulfonates and mono-,di- and tri-Ci-Ci6-alkylnaphthaline sulfonates.
  • Ci-Ci6-alkylarene sulfonates such as mono-, di- and tri- Ci-Ci6-alkylbenzene sulfonates and mono-,di- and tri-Ci-Ci6-alkylnaphthaline sulfonates.
  • anionic surfactants of component d) are dibutylnaphtaline sulfonate, dodecyldiphenylether sulfonate, cumyl sulfonate, octylbenzene sulfonate, nonylbenzene sulfonate, dodecylbenzene sulfonate and tridecylbenzene sulfonate.
  • Preferred anionic surfactants d) are mono- or di-C4-C8-alkylnaphthaline sulfonic acids and mono- or di-C4-Ci6-alkylbenzene sulfonic acids, in particular mono-C4-Ci6- alkylbenzene sulfonic acids, and the alkaline metal salts, such as the sodium or potassium salts, and the earth alkaline metal salts, in particular the calcium salts, and the ammonium salts and the substituted ammonium salts, in particular alkyl substituted ammonium salts, thereof.
  • the anionic surfactants d) are commercially available e.g. under the trade name Wettol ® EM1 (BASF), Wettol ® NT1 (BASF), Rhodacal ® 70
  • Particularly preferred anionic surfactants d) are mono- and di-Cs-C-u-alkylbenzene sulfonic acids, in particular the mono-Cs-C-u-alkylbenzene sulfonic acids, such as dodecylbenzene sulfonic acids with linear or branched alkyl moieties, including the earth alkaline metal salts, in particular the calcium salts, and the alkyl substituted ammonium salts, in particular the isopropyl ammonium salts, thereof.
  • the total amount of anionic surfactant d) will, as a rule, not exceed 40% by weight, in particular 30% by weight, based on the total weight of the formulation according to the invention and is typically in the range from 0.5 to 40% by weight, in particular in the range from 1 to 30% by weight and specifically in the range of from 2 to 25% by weight, based on the total weight of the formulation according to the invention.
  • the formulations of the present invention may optionally further contain at least one anionic surfactant f) that differs from anionic surfactants d).
  • Anionic surfactants f) are preferably selected from the surfactant groups f1 ), f2), f3), f4), f5), f6) and f7) as defined herein below.
  • the anionic surfactants of group f1 are selected from the alkaline metal salts, the earth alkaline metal salts and the ammonium salts of sulfated polyethoxylates of
  • Preferred surfactants f1 ) are the ammonium salts of sulfated polyethoxylates of tristyryl phenols, in particular of 2,4, 6-tristyryl phenols.
  • the anionic surfactants f1 ) are commercially available e.g. under the trade name
  • Soprophor ® 4D 384 (Rhodia).
  • the anionic surfactants of group f2) are selected from the alkaline metal salts, the earth alkaline metal salts and the ammonium salts of di-C4-Ci6-alkylesters of sulfosuccinic acid.
  • Preferred surfactants f2) are the sodium, potassium, calcium or ammonium salts of di-C6-Ci2-alkylesters of sulfosuccinic acid, in particular the sodium salt of
  • the anionic surfactants f2) are commercially available e.g. under the trade name Aerosol ® OT-A (Cytec).
  • the anionic surfactants of group f3) are selected from polymeric anionic surfactants having SO3 " groups bound to an aromatic moiety such as a phenyl or a naphthyl ring, e.g. condensates of arylsulfonic acid with formaldehyde and optionally in addition with urea, such as naphthalene sulfonic acid formaldehyde condensates, phenol sulfonic acid formaldehyde condensates, cresol sulfonic acid formaldehyde condensates, ligninsulfonates, etc.
  • the arylsulfonic acids incorporated into said formaldehyde condensates may be e.g. phenol sulfonic acids or naphthalene sulfonic acids which are unsubstituted or substituted by one or more, e.g. 1 , 2, 3 or 4 C1-C20 alkyl groups.
  • Preferred surfactants f3) are the alkaline metal salts or earth alkaline metal salts of reaction products (condensates) of phenol sulfonic acid and formaldehyde.
  • the anionic surfactants f3) are commercially available e.g. under the trade names Tamol ® DN (BASF), Tamol ® PP and Wettol ® D1 (BASF).
  • the anionic surfactants of group f4) are selected from the sodium, potassium, calcium and ammonium salts of C6-C22-alkyl sulfonates and C6-C22-alkyl sulfates, such as lauryl sulfonate, isotridecyl sulfonate, lauryl sulfate, isotridecyl sulfate, cetyl sulfate and stearyl sulfate.
  • the anionic surfactants of group f5) are selected from the sodium, potassium, calcium and ammonium salts of sulfates and sulfonates of C6-C22-fatty acids and C6-C22-fatty acid esters.
  • the anionic surfactants of group f6) are selected from the sodium, potassium, calcium and ammonium salts of sulfates of polyethoxylated C6-C22 alkanols, such as sulfates of polyethoxylated lauryl alcohol.
  • the anionic surfactants of group f7) are selected from the sodium, potassium, calcium and ammonium salts of sulfates of polyethoxylated C4-Ci6-alkylphenols.
  • the total amount of anionic surfactants f), if present, is preferably in the range from 0.1 to 20 % by weight, in particular from 0.5 to 15 % by weight, more preferably from 1 to 10 % by weight, based on the total weight of the formulation.
  • the aforementioned surfactants which may also be referred to as surface-active substances, are known to the skilled worker. An overview can be found, for example, in McCutcheon ' s "Detergents and Emulsifiers Annual", MC Publ.
  • the formulation of the invention comprises:
  • Ci6-alkylarene sulfonates Ci6-alkylarene sulfonates
  • compositions according to the invention may also comprise customary adjuvants, such as viscosity-modifying additives (thickeners), anti-drift agents, adhesives, penetrants, antifoam agents, preservatives, inorganic dispersants, antifreeze agents, antioxidants, colorants, aromatic substances, etc, which are usually employed in oil formulations of herbicides.
  • customary adjuvants such as viscosity-modifying additives (thickeners), anti-drift agents, adhesives, penetrants, antifoam agents, preservatives, inorganic dispersants, antifreeze agents, antioxidants, colorants, aromatic substances, etc, which are usually employed in oil formulations of herbicides.
  • the amount of additives will generally not exceed 15% by weight, in particular 10% by weight of the total weight of the composition.
  • Suitable thickeners are compounds which affect the rheological properties of the oil suspension concentrate, even when used in small amounts. These include in particular all substances which increase the viscosity of oils, specifically those which are suitable for plant protection formulations.
  • Suitable thickeners are:
  • Bentone ® Elementis
  • Attagel ® Engelhard
  • Agsorb ® Oil-Dri Corporation
  • Hectorite ® Hectorite ® (Akzo Nobel)
  • silicates or silicic acids in particular highly disperse silicates and silicic acids from the Sipernat ® , Aerosil ® or Durosil ® series (Degussa), the CAB-O-SIL ® series (Cabot) or the Van Gel series (RT. Vanderbilt),
  • organic thickeners for example those based on hydrogenated fatty acids and fatty acid derivatives, such as thickeners from the Thixin ® or Thixatrol ® series (Elementis), and thickeners based on synthetic polymers, for example polyalkyl(meth)acrylates, polyamide thickeners, polyurethane thickeners, xanthan gum, for example the products sold under the name Rhodopol ® (Rhodia) and Kelzan ® S (Kelco Corp.).
  • synthetic polymers for example polyalkyl(meth)acrylates, polyamide thickeners, polyurethane thickeners, xanthan gum, for example the products sold under the name Rhodopol ® (Rhodia) and Kelzan ® S (Kelco Corp.).
  • Preferred thickeners are those based on natural or synthetic silicates and silicic acids, for example the substances mentioned in groups g1 ) and g2).
  • concentration of thickeners in the final aqueous concentrates will generally not exceed 7% by weight, based on the total weight of the final aqueous concentrate, and is preferably in the range from 0.1 to 7% by weight, in particular from 0.2 to 5% by weight and especially from 0.5 to 3% by weight, based on the total weight of the final suspension
  • Suitable antifreeze agents are those from the group of the ureas, diols and polyols, such as ethylene glycol and propylene glycol.
  • Suitable antifoams are those based on silicones.
  • Suitable inorganic dispersants, also termed anticaking agents, for preventing agglutination of the a.i. particles are silica (such as, for example Sipernat ® 22 from Degussa), alumina, calcium carbonate and the like.
  • Suitable preservatives, colorants and perfumes are known to the skilled worker, for example from the literature mentioned above in connection with surfactants, and from Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J.; H. v. Olphen, "Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley & Sons, N.Y.; and C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y. 1963.
  • the oil suspension concentrates according to the invention can be prepared by methods known per se for the preparation of oil suspension concentrates, for example by mixing components a) to f) and, if appropriate further adjuvants.
  • components a) to f) and, if appropriate further adjuvants For example, it is possible for example to initially introduce component b) and optionally component e), followed by the addition of components a), c), d), f), if appropriate residual amounts of b) and e), and, if appropriate, further adjuvants.
  • b) optionally together with e) may also be mixed with a thickener before the remaining components are added.
  • the resulting oil suspension can subsequently be subjected to fine-milling, if appropriate after a preliminary milling step. Milling and grinding are used synonymously herein to refer to any suitable physical attrition method, such as grinding, crushing or milling.
  • Customary mixing devices which, if appropriate, can be heated may be used for preparing the mixtures.
  • high-pressure homogenizers or mills which operate on the rotor-stator principle such as Ultraturax homogenizers, for example from IKA, or toothed colloid mills, for example from Puck.
  • Apparatus which can be used for the fine-grinding step can be, for example, batchwise-operating bead mills, for example from Drais, or continuously-operating bead mills, for example from Bachofen.
  • the preparation process can be adapted and, if appropriate, a pre-grinding step or else a fine-grinding step can be dispensed with.
  • the particle sizes of the particles of component a) present in the suspension are typically reduced to below 20 ⁇ , preferably to below 10 ⁇ and in particular to below 5 ⁇ (Dgo-value).
  • Components a) to f) and, if appropriate, further adjuvants, which are employed for the preparation of the formulations may comprise, as secondary component, water, which is recovered in the oil suspension concentrates according to the invention. Therefore, the oil suspension concentrates according to the invention may comprise small amounts of water, in general no more than 5% by weight, in particular no more than 1 % by weight, based on the total weight of the formulation.
  • the invention also relates to uses of the liquid suspension concentrate formulation of the invention for protecting crop plants and to methods of controlling undesired vegetation, which comprise applying the formulations, in diluted or undiluted form, to plants, their environment and/or seeds.
  • the herbicidal formulations of the invention affect a very good control of vegetation in non-crop areas, especially at high application rates.
  • crops such as soybean, cotton, oilseed rape, flax, lentils, rice, sugar beet, sunflower, tobacco and cereals, such as, for example maize or wheat, they are active against broad-leaved weeds and grass weeds without inflicting substantial damage to the crop plants. This effect is particularly observed at low application rates.
  • the formulations of the invention can additionally be employed in a further number of crop plants to remove undesired plants. Crops which are suitable are, for example, the following:
  • formulations of the invention can also be used in crops which tolerate the effect of herbicides as the result of breeding, including genetic engineering methods.
  • formulations of the invention can also be used in crops which tolerate attack by insects or fungi as the result of breeding, including genetic engineering methods.
  • formulations of the invention are also suitable for the defoliation and desiccation of plant parts, for which crops plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • the formulations of the invention are particularly suitable for desiccating the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean. This makes possible the fully mechanical harvesting of these important crop plants. Also of economic interest is to facilitate harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives or other species and varieties of pome fruit, stone fruit and nuts.
  • the same mechanism i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
  • a shortening of the time interval within which the individual cotton plants mature leads to an increased fiber quality after harvesting.
  • formulations of the invention are also suitable for the control of conifers, in particular of conifer seedlings which grow naturally, and specifically for the control of pine seedlings which grow naturally.
  • liquid suspension concentrate formulations described herein are useful for combating undesired vegetation.
  • the formulations may be applied as such or are preferably applied after dilution with water.
  • a so-called aqueous spray-liquor is prepared by diluting the suspension concentrate formulation of the present invention with water, e.g. tap water.
  • the spray-liquors may also comprise further constituents in dissolved, emulsified or suspended form, for example fertilizers, active substances of other groups of herbicidal or growth-regulatory active substances, further active substances, for example active substances for controlling animal pests or phytopathogenic fungi or bacteria, furthermore mineral salts which are employed for alleviating nutritional and trace element deficiencies, and nonphytotoxic oils or oil concentrates.
  • these constituents are added to the spray mixture before, during or after dilution of the formulations according to the invention.
  • the formulations of the invention can be applied by the pre-emergence or the post- emergence method.
  • saflufenacil is less well tolerated by certain crop plants
  • application techniques may be employed where the herbicidal compositions are sprayed, with the aid of the spraying apparatus, in such a way that the leaves of the sensitive crop plants ideally do not come into contact with them, while the active substances reach the leaves of undesired plants which grow underneath, or the bare soil surface (post-directed, lay-by).
  • the formulations of the invention are applied to such a degree that the application rates of saflufenacil are from 0.001 to 3.0, preferably from 0.01 to 1 .0 kg/ha active substance (a.s.).
  • liquid suspension concentrate formulations of the invention can be mixed with a large number of representatives of other groups of herbicidal or growth-regulatory active substances and applied together with these.
  • suitable mixing partners are 1 ,2,4-thiadiazoles, 1 ,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy/heteroaryl- oxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothia- diazinones, 2-(hetaroyl/aroyl)-1 ,3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran- 3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls
  • the liquid suspension concentrate formulations of the present invention can be mixed and applied together with a large number of different pesticide compound formulations, for example those that include active ingredients or adjuvants, such as atrazine, glyphosate, glufosinate, S-metolachlor, 2,4-D ester, isoxaflutole, diflufenzopyr, dicamba, mesotrione, dimethenamid-P, pendimethalin, imazethapyr, paraffin oils, polyol fatty acid esters, polyethoxylated polyol fatty acid esters, ethoxylated alkyl aryl phosphates, methylated seed oils, emulsifiers, ammonium sulfate or mixtures thereof.
  • active ingredients or adjuvants such as atrazine, glyphosate, glufosinate, S-metolachlor, 2,4-D ester, isoxaflutole, diflufenzopyr, dic
  • formulations of the invention may be useful to apply the formulations of the invention, separately or in combination with other herbicides, jointly as a mixture with yet further plant protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria.
  • Particle sizes were determined by dynamic light scattering with a Malvern Mastersizer 2000 system at 23°C.
  • Viscosities were measured in analogy to DIN EN ISO 255 with a Brookfield DV-E Viscometer, spindle 1 of the RV spindle set at 50 nr 1 .
  • dynamic viscosities were determined in analogy to OECD Test Guidline 1 14 ("Viscosity of Liquids").
  • Surfactant N1 polyethoxylated linear Ci3-Cis-alcohol (3 EO units) - Lutensol ® A03 (BASF);
  • Surfactant N2 polyethoxylated branched Ci3-alcohol (3 EO units) - Lutensol ® T03 (BASF);
  • Surfactant N3 poly-ethoxy-co-propoxylated butanol - AtlasTM G 5000
  • Surfactant N4 poly(12-hydroxystearic acid)-polyoxyethylene - HypermerTM
  • Surfactant N5 polyethoxylated castor oil (31 EO units - Wettol ® EM 31
  • Surfactant N6 polyethoxylated tristyryl phenol - Soprophor BSU (Rhodia); Surfactant A1 : calcium salt of dodecylbenzene sulfonate in 2-ethylhexan-1 - ol (60 %(v/v)) - Wettol ® EM 1 (BASF);
  • Diluent 2 aliphatic hyddrocarbons within a boiling range of form 208 to
  • ExxsolTM D80 (ExxonMobil Chemical); Diluent 3 predominantly Cio- and C -alkyl naphthalines within a boiling range of form 235 to 305°C, naphthaline depleted - Solvesso ® 200 ND (ExxonMobil Chemical);
  • Thickener 1 magnesium aluminum silikates - Attagel ® 50 (Engelhard);
  • Adjuvant 1 mixture of mixed fatty acid methyl esters plus a surfactant blend - Dash ® HC (BASF).
  • Example 3 For each Example listed in table 3 about 1000 ml. of either Diluent 1 , 2 or 3, as indicated in table 3, was introduced into a receiving vessel and saflufenacil anhydrate and Thickener 1 , if appropriate, were added. After mixing with an Ultra-Turax ® , the suspension was milled with the aid of a Dynomill ® mill at a speed of approximately 3000 min- 1 and an exit temperature of 25 to 30 °C. Thereafter, the mixture of surfactants N and A, as given in table 3 were incorporated using an Ultra-Turrax ® . Finally the suspension was filled up to 1 liter with either Diluent 1 , 2 or 3, optionally subjected to an additional milling step and stirred for further 20 minutes.
  • the stabilities of stored formulations were evaluated on the basis of the quality of the dispersions obtained therefrom by dilution.
  • Example 2 Initially a sample of the formulation that was freshly prepared according to Example 1 was diluted with water (2g in 98g water) in analogy to the preparation of a spray liquor. A stable white dispersion without sediment was obtained.
  • Samples of the formulation were then stored at 20°C, 30°C, 40°C and 50°C, respectively, for a period of 6 months and afterwards diluted with water as described above.
  • the resulting dispersions were examined for their physical properties after storage for 2 hours at 20°C. In all cases no or only minor sedimentation accounting for less than 2 % of the total weight of the saflufenacil was observed.
  • test plants listed below were first grown, depending on the plant habit, to a height of 3 to 20 cm. Only then they were treated in parallel with spray liquors that include either the formulation according to Example 1 or a WG formulation containing saflufenacil (Heat 70 WG (BASF) or Treevix WG (BASF), each containing 70% by weight of saflufenacil). In both cases the spray liquors were prepared by dilution with water to levels customary for saflufenacil. The test plant were sprayed using finely distributing nozzles to the extent that the application rates of saflufenacil given in table 4 were reached. The test period extended over 42 days. During this time, the plants were tended, and their response to the treatments with active compound was evaluated.
  • spray liquors that include either the formulation according to Example 1 or a WG formulation containing saflufenacil (Heat 70 WG (BASF) or Treevix WG (BASF), each containing 70% by weight of s
  • the evaluation for the damage caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants.
  • 0 means no damage and 100 means complete destruction of the plants.
  • Eclipta alba ECLAL false daisy Table 4 relates to the herbicidal activity of saflufenacil assessed 7, 21 and 42 days after treatment (DAT).
  • Example 1 suspension concentrate of Example 1 and a conventional WG formulation
  • test plants listed below were first grown, depending on the plant habit, to a height of 3 to 20 cm. Only then they were treated in parallel with spray liquors that include either the formulation according to Example 1 or a WG formulation containing saflufenacil (Heat 70 WG (BASF) or Treevix WG (BASF), each containing 70% by weight of saflufenacil). In both cases the spray liquors were prepared by dilution with water to levels customary for saflufenacil and by adding Adjuvant 1 to a concentration of 0.5% (v/v). The test plant were sprayed with these spray liquors using finely distributing nozzles to the extent that the application rates of saflufenacil given in table 5 were reached.
  • spray liquors that include either the formulation according to Example 1 or a WG formulation containing saflufenacil (Heat 70 WG (BASF) or Treevix WG (BASF), each containing 70% by weight of saflufenacil).
  • the test period extended over 51 days. During this time, the plants were tended, and their response to the treatments with active compound was evaluated. The evaluation for the damage caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plants.
  • the plants used in the greenhouse experiments belonged to the following species:
  • Table 5 relates to the herbicidal activity of saflufenacil assessed 19, 35 and 51 days after treatment (DAT).
  • test plants listed below were first grown, depending on the plant habit, to a height of 3 to 20 cm. Only then they were treated in parallel with spray liquors that include either the formulation according to Example 1 or an aqueous SC saflufenacil formulation (containing 342 g/L saflufenacil anhydrate). In both cases the spray liquors were prepared by dilution with water to levels customary for saflufenacil. The test plant were sprayed using finely distributing nozzles to the extent that the application rates of saflufenacil given in table 6 were reached. The test period extended over 21 days. During this time, the plants were tended, and their response to the treatments with active compound was evaluated.
  • the evaluation for the damage caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants.
  • 0 means no damage and 100 means complete destruction of the plants.
  • Table 6 relates to the herbicidal activity of saflufenacil assessed 7 and 21 days after treatment (DAT).
  • test plants listed below were first grown, depending on the plant habit, to a height of 3 to 20 cm. Only then they were treated in parallel with spray liquors that include either the formulation according to Example 1 or an aqueous SC saflufenacil formulation (containing 342 g/L saflufenacil anhydrate). In both cases the spray liquors were prepared by dilution with water to levels customary for saflufenacil and by adding Adjuvant 1 to a concentration of 0.5% (v/v). The test plant were sprayed with these spray liquors using finely distributing nozzles to the extent that the application rates of saflufenacil given in table 7 were reached.
  • spray liquors that include either the formulation according to Example 1 or an aqueous SC saflufenacil formulation (containing 342 g/L saflufenacil anhydrate). In both cases the spray liquors were prepared by dilution with water to levels customary for saflufenacil and by adding Adjuvant
  • the test period extended over 51 days. During this time, the plants were tended, and their response to the treatments with active compound was evaluated. The evaluation for the damage caused by the chemical compositions was carried out using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plants.
  • Table 7 relates to the herbicidal activity of saflufenacil assessed 12, 25, 35 and 51 days after treatment (DAT).
  • the formulation according to the invention shows clearly superior herbicidal activitiy against a variety of weed targets in comparison to conventional formulations having the same levels of saflufenacil.

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Abstract

La présente invention concerne des formulations de concentré de suspension liquide pour la protection des plantes, qui comprennent : du 2-chloro-5-[3,6-dihydro-3-méthyl-2,6-dioxo-4-(trifluorométhyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[méthyl(1-méthyléthyl)amino]sulfonyl]benzamide sous la forme de l'anhydrate cristallin; au moins un diluant choisi parmi : les solvants hydrocarbonés ayant un point d'ébullition d'au moins 100°C; et les esters d'alkyle en C1-C8 d'acides gras en C8-C26, les mono- et di-(alkyl en C1-C4) amides d'acides gras en C8-C26; au moins deux surfactants non ioniques différents choisis parmi les poly-éthoxylate-co-(alkoxylates en C3-C4) d'alcanols en C3-C20, les polyéthoxylates d'alcanols en C8-C22, les copolymères séquencés polyester-polyoxyéthylène, les polyéthoxylates de mono-, di- ou tristyryl phénols et les polyéthoxylates d'huiles végétales; et au moins un surfactant anionique choisi parmi les (alkylarène en C1-C16) sulfonates.
PCT/EP2010/069133 2009-12-09 2010-12-08 Formulations de concentré de suspension liquide contenant du saflufénacil WO2011070051A2 (fr)

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AU2010329961A AU2010329961B2 (en) 2009-12-09 2010-12-08 Liquid suspension concentrate formulations containing saflufenacil
CN201080055652.5A CN102655748B (zh) 2009-12-09 2010-12-08 含有苯嘧磺草胺的液体悬浮浓缩物配制剂
BR112012013151-6A BR112012013151B1 (pt) 2009-12-09 2010-12-08 Formulation of liquid suspension concentrate for plant protection, use of concentration of liquid suspension for plant protection and undesired vegetation control method
US13/512,623 US8703650B2 (en) 2009-12-09 2010-12-08 Liquid suspension concentrate formulations containing saflufenacil
CA2782759A CA2782759C (fr) 2009-12-09 2010-12-08 Formulations de concentre de suspension liquide contenant du saflufenacil

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US28503409P 2009-12-09 2009-12-09
US61/285,034 2009-12-09

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WO2011070051A2 true WO2011070051A2 (fr) 2011-06-16
WO2011070051A3 WO2011070051A3 (fr) 2011-10-27

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US8653002B2 (en) 2009-08-27 2014-02-18 Basf Se Aqueous suspension concentrate formulations containing saflufenacil
US8778838B2 (en) 2009-08-27 2014-07-15 Basf Se Aqueous concentrate formulations containing saflufenacil and glyphosate
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US9545104B2 (en) 2009-12-09 2017-01-17 Basf Se Liquid suspension concentrate formulations containing saflufenacil and glyphosate
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Cited By (6)

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Publication number Priority date Publication date Assignee Title
US8653002B2 (en) 2009-08-27 2014-02-18 Basf Se Aqueous suspension concentrate formulations containing saflufenacil
US8778838B2 (en) 2009-08-27 2014-07-15 Basf Se Aqueous concentrate formulations containing saflufenacil and glyphosate
US9545104B2 (en) 2009-12-09 2017-01-17 Basf Se Liquid suspension concentrate formulations containing saflufenacil and glyphosate
WO2015145105A1 (fr) * 2014-03-25 2015-10-01 Croda International Plc Concentrés agrochimiques à base d'huile
US9861100B2 (en) 2014-03-25 2018-01-09 Croda International Plc Agrochemical oil based concentrates
WO2024042134A1 (fr) 2022-08-26 2024-02-29 BASF Agro B.V. Formulations herbicides aqueuses

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CN102655748B (zh) 2015-11-25
WO2011070051A3 (fr) 2011-10-27
BR112012013151B1 (pt) 2017-07-25
AU2010329961B2 (en) 2014-12-04
CA2782759A1 (fr) 2011-06-16
CA2782759C (fr) 2021-07-13
BR112012013151A2 (pt) 2015-09-15
US20120302444A1 (en) 2012-11-29
AU2010329961A1 (en) 2012-06-21
CN102655748A (zh) 2012-09-05
US8703650B2 (en) 2014-04-22

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