Formulation Technology Dr. Murat Mertoglu Denmark, September 6, 2012
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1 Formulation Technology Dr. Murat Mertoglu Denmark, September 6, 2012
2 Outline Definition of formulation Formulation types Requirement of formulations Delivery of actives to target vs. formulation Exercise: lets chose a formulation type Future trends: more sustainable formulations Summary 2
3 What Does the Term Formulation Mean? Definition: Formulation is the process of converting an active ingredient (or technicalmaterial) into an applicable product. Flat Cake Cheese Cake You cannot get a good product only by using good active ingredients, formulation also plays a key role in the success of a product on the field! 3
4 Formulation Technology Codes of Plant Protection Products International coding Search for: Technical Monograph No2 63 codes (+ 29 abandoned) Code EC SL DC SC SE FS OD EW ME CS WG WP Description Emulsifiable concentrate Soluble concentrate Dispersible concentrate Suspension concentrate Suspoemulsion Flowable concentrate for seed treatment Dispersion in oil Emulsion, oil in water Microemulsion Capsule suspension Water dispersible granule Wettable powder 4
5 Choice of Formulation Type biological efficacy systemic, and/or contact intrinsic physical and chemical properties liquid/ solid, melting point, solubility, stability, volatile, etc...) type application (herbicide, insecticide, fungicide) type of crop (cereals, specialty crop ) regulatory eye tox, tank mix additive, smell, drift packaging ( 5 lt, 10, 50 lt, 1000 lt) plays a key role in the field the performance and the market success 5
6 Simple Classification 6
7 Simple Classification 7
8 Liquid Formulation EC (ME) emulsion DC a.i. particles < 150 nm SL a.i. dissolved dilute in water X 400 8
9 Liquid Formulation a.i. crystal a.i.+ solvent solvent water dilute in water X 400 9
10 Typical additives for continuous phase water SC, SE, EW dispersing agent, antifreeze, thickener, bactericide, antifoaming agent emulsifier solvent, adjuvants (to improve spreading, uptake, retention), crystallization inhibitors, stabilizers (buffer, antioxidant, etc..) a) steric b) electrostatic c) electrostatic + steric stabilization 06/09/ 2012 Dr. Murat Mertoglu (BASF SE) 10
11 Typical additives for continuous phase water Inhibitor polymer 12x weeks at 40 C 12x weeks at 40 C boscalid 250 g/l antifreeze 70 g/l dispersing agent a 20 g/l dispersing agent b 30 g/l antifoam 5 g/l thickener 2 g/l bactericide 2 g/l inhibitor 2 g/l water add 1 lt * CH 2 HO CH 3 CH 2 CH CH 3 CH n 2 R n O O O CH 3 n * Particle size distribution d 90 (µm) without initial after 12 weeks d 90 (µm) with 2% no crystal growth with polymer, and so no nozzle blockage 11 Confidential
12 Typical additives for continuous phase solvent EC, DC, OD, solvent emulsifier dispersing agent, thickener adjuvants (to improve spreading, uptake, retention), /09/ 2012 a) steric b) electrostatic c) electrostatic + steric stabilization Dr. Murat Mertoglu (BASF SE) 12
13 Requirements for Liquid Formulations Active loading 100g- 500 g /lt (in general) Viscosity < 200 mpa/s Chemical stability: maximum 5 % a.i. Decomposition allowed For 2 years and 8 weeks at 40 C Physical stability at ambient temperature for 2-3 years at 0 C to 40 C for several day X 30 µm 30 µm 30 µm 30 µm Concentate Phase separation Coalescence Flocculation Crystal growth 13
14 Dry (solid) Formulations spontaneous dispersibility is requested! Limited number additives technology intensive Low cost of goods Relatively higher production cost! 14
15 Delivery Properties Spraying Retention or Anti-bouncing Wetting Dynamic surface tension Penetration Absorption Static surface tension Fixation Structure of particles Contact angle Distribution Uptake Evaporation / Adhesion Spreading An effective active and a stable formulation are not alone enough! 15
16 Drift Reduction Spraying (Atomization) the smaller are the size of droplets, the larger is the drift problem! 16
17 Retention (Deposition) Retention R Rioboo et al. (2001). Outcomes from a drop impact on solid surfaces. At. Sprays 11: sprayed pesticide droplets must remain on the plant! 17
18 Spray Retention % Retention Improvement via Formulation Générateur de gouttelettes Caméra: prises/seconde Source de lumière Support d échantillon 0 WaterSC (1) EC (1+2) Epoxiconazole (SC) Epox.(SC) + Metco (EC) Epox. + Metco. (EC) 18
19 Contact Angle 1s 10s 60s 19
20 Spreading Spreading Water SC SE spreading is particularly important for contact fungicides 20
21 Adhesion REM Pictures Structure of particles 2000 : : 1 better contact with leave surface: good for uptake & rain fastness 21
22 Barriers for Uptake of A.I. Transverse section of a wheat leaf Absorption Epidermal cell Epicuticular wax Cuticle Epicuticular waxes Cuticle with embedded waxes Epidermal cells on leaf in waxy layer in leaf (uptake) waxy layer and the cuticle barrier for active ingredient uptake 22
23 Through the Barrier Absorption a.i. diffusion path without adjuvant a.i. diffusion path with adjuvant Uptake depends: on plant type intrinsic mobility of active used solvents and/or adjuvants (non ionic surfactants: fatty alcohol alkoxylated) Special adjuvants and/or solvents opens channels in crystalline wax layer after M. Riederer, Würzburg 23
24 Formulation Development Exercise! septoria tritici days green leaf tissue chlorosis dry lesion + pycnidia spore-germination infection mycelial growth pycnidia sporulation Spore germination Superficial hyphal growth Penetration Subepidermal runner hyphae Latent mycelium Necrotrophic mycelium Pycnidium formation Cirrhus production & spore extrusino carboxamide conazole Preventative action Curative action No efficacy with fungicides It could be used effectively within 12 days after an infection to save the plants! 24
25 Formulation Development Exercise! Actives: boscalid + epoxiconazole + pyraclostrobin Chose formulation type, but consider requirements & intrinsic properties! uptake of epoxiconazole & pyraclostrobin: apply molecularly dissolved form + adjuvant spreading of boscalid on the surface boscalid is not soluble in registered solvents pyraclostrobin has low melting point pyraclostrobin & boscalid: not compatible with adjuvants; crystallization rain fastness 25
26 Formulation Development Exercise! 1 st active (a.i.) 2 nd active (a.i.) solvent water EC solution of SL solution of active in water SC dispersed a.i. (crystalline in water a.i in solvent OD dispersion of crystalline a.i in solvent ME micro - emulsion EW emulsion of dissolved a.i in water SE combination of SC + EW 26
27 Formulation Development Exercise Pseudo= OD+ EC 1 st active (a.i.) solvent 2 nd (a.i.)+solvent + = water OD dispersion of crystalline a.i in solvent EC solution of a.i in solvent OD dispersion of crystalline a.i in solvent Boscalid conazole + strobin. dilution OD OD Pseudo OD fulfills all requirements for maximum biological efficacy! 27
28 % % Formulation Development Ex. OD vs. Tank Mix (SC + SE) Uptake Boscalid (SC) + Pyrac.&Epoxi. (SE) wash uptake boscalid epoxiconazole pyraclostrobin OD wash uptake boscalid epoxiconazole pyraclostrobin OD provided improved uptake of epoxiconazole and pyraclostrobin 28
29 OD vs. Tank Mix (SC + SE) Spreading Spreading ~ 120 % Spreading > 1000% Improved spreading for boscalid : better spreader in formulation 29
30 Rain Fastness Via quantitative Determination of A.I. Uptake Application not irrigated Drying over night Collection of leaves Active in&on leaf Drying Time typically 1h Irrigation irrigated Drying over night Collection of leaves Analysis with LC-MS-MS Active in&on leaf new methods: quantitative determination of un-labeled a.i.s. 30
31 OD vs. Tank Mix (SC + SE) Rain Fastness Glasshouse test brown rust 3 days curative: Application 3 days after inoculation without irrigation 15 min after application (20mm) 60 min after application (20mm) Tank Mix OD Untreated % brown rust attack Improved as rain fastness with = right formulation type for this mixture! 31
32 Future: more sustainable pesticides formulations No compromise on performance Less chemical /ha Chemicals with better profile More convenient for farmer More profitable 32
33 Performance Description of Technical Target Typically EC Target High performance Free from critical solvents & inerts Typically SC Sustainability 33
34 Performance More Sustainable Formulation Example Epox. Metc. Mixture with Tailored Polymer Polymer CP 633, custom made for conazoles, partially replace solvents 30% more azole loading: 2 lt/ha instead of 3 lt/ha co-solvent, dispersing agent, adjuvant, retention improver, beter rain fastness with CP633 without CP633 Enhanced bio-availability Performance Target Less solvents Sustainability Boost formul. properties Efficiency Reduced volume Convenience Sustainability 34
35 How does polymer CP 633 works! Hydrophilic element Lipophilic element A.I. element Active ingredients Hydrophilic element Diluted in water Lipophilic element A.I. element Active ingredients Polymer at least with three different functional groups 35 35
36 Conazole Mixture in Polymer EC Quick uptake allows strong curative action and excellent rain fastness 36
37 Different properties are improvable, but no perfect formulation superior in all properties exists! Stability, Tox & Ecology Drift, Efficacy Retention, Cost Spreading, Manufacturing Uptake, IP Rain Fastness Marketing: Profitable product Formulation Stability, Drift, Retention, Spreading, Uptake, Rain Fastness Authorities: tox & ecotox profile Customer: Effective Product Good formulations are the ones that finds the best compromise among needs of customers, authorities, environment, and producers! 37
38 Backup Slides! 06/09/ 2012 Dr. Murat Mertoglu (BASF SE) 38
39 Bead milling: basis for SC, SE, OD, etc Active ingredients Formulants Water bead mill SC ~ 200 µ ~ 80 % <2 µ EC Beads SE Bead mill 1. Rotor 2. Inlet 3. Grinding beads 4. Cooling jacket 5. Separation system 39
40 Dry (solid) Formulations Wetable Granulate (WG) Fluidized bed granulation Active ingredient + formulants + water Exhaust air Drying air Wet milling Suspension 40
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