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New Glyphosate formulation with reduced impact for the Environment Uses of APP surfactants as the green adjuvants Cédric Ernenwein 2 , Sophie Leporini 1 , Philippe Kueneman 3 , Corine Lajoie 3 Application Note N° 02 Route de Bazancourt - 51110 Pomacle, France - Tel.: +33 (0)3 26 88 84 10 Fax: +33 (0)3 26 88 84 11 www.wheatoleo.com - [email protected] INTRODUCTION This poster has been presented during the 9 th international symposium on adjuvants for agrochemicals, ISAA 2010. This work is a collaborative project between WHEATOLEO, the first producer of APP (pentosides Surfactant) and PHYTEUROP, the first French independent industrial Group, active in manufacturing, formulation and distribution of agrochemical products. Driven by environmental and regulatory considerations, this project shows how an alternative glyphosate formulation strategy can give a good ratio between efficiency and safety. APPYCLEAN SURFACTANTS: NEW CLASS OF GREEN ADJUVANTS Alkyl Polypentoside (or APP) are a new class of surfactants coming from agricultural renewable resources. Hydrolysis of hemicellulose (e.g. wheat straw or bran) under acidic or enzymatic conditions, gives a syrup rich in C5 sugars (xylose and arabinose). These pentoses are grafted on natural alcohols in a Fisher’s glycosilation synthesis to obta in a new range of non-ionic surfactants, called APP. Figure 1 : schematic production of pentosides surfactants (or APP) * Contact angle measured at 01% w/w , 25°C on PTFE plate (117 ° for water) ** According to Drave’s test on normalized coton disc, time to sink.

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Page 1: New Glyphosate formulation with reduced impact for the ... · PDF fileNew Glyphosate formulation with reduced ... characteristics for agrochemicals formulations ... New Glyphosate

New Glyphosate formulation with reduced impact for the Environment

Uses of APP surfactants as the green adjuvants Cédric Ernenwein2, Sophie Leporini1, Philippe Kueneman3, Corine Lajoie3

Application Note N° 02

Route de Bazancourt - 51110 Pomacle, France - Tel.: +33 (0)3 26 88 84 10 – Fax: +33 (0)3 26 88 84 11 www.wheatoleo.com - [email protected]

INTRODUCTION

This poster has been presented during the 9th

international symposium on adjuvants for agrochemicals, ISAA 2010. This work is a collaborative project between WHEATOLEO, the first producer of APP (pentosides Surfactant) and PHYTEUROP, the first French independent industrial Group, active in manufacturing, formulation and distribution of agrochemical products. Driven by environmental and regulatory considerations, this project shows how an alternative glyphosate formulation strategy can give a good ratio between efficiency and safety.

APPYCLEAN SURFACTANTS: NEW CLASS OF GREEN ADJUVANTS

Alkyl Polypentoside (or APP) are a new class of surfactants coming from agricultural renewable resources. Hydrolysis of hemicellulose (e.g. wheat straw or bran) under acidic or enzymatic conditions, gives a syrup rich in C5 sugars (xylose and arabinose). These pentoses are grafted on natural alcohols in a Fisher’s glycosilation synthesis to obta in a new range of non-ionic surfactants, called APP.

Figure 1 : schematic production of pentosides surfactants (or APP)

* Contact angle measured at 01% w/w , 25°C on PTFE plate (117 ° for water) ** According to Drave’s test on normalized coton disc, time to sink.

Page 2: New Glyphosate formulation with reduced impact for the ... · PDF fileNew Glyphosate formulation with reduced ... characteristics for agrochemicals formulations ... New Glyphosate

New Glyphosate formulation with reduced impact for the Environment

Uses of APP surfactants as the green adjuvants Cédric Ernenwein2, Sophie Leporini1, Philippe Kueneman3, Corine Lajoie3

Application Note N° 02

Route de Bazancourt - 51110 Pomacle, France - Tel.: +33 (0)3 26 88 84 10 – Fax: +33 (0)3 26 88 84 11 www.wheatoleo.com - [email protected]

Table 1 : Range of Appyclean and characteristics for agrochemicals formulations

Appyclean surfactants are readily biodegradable according to OECD 301F guideline and exhibit a low bionotox profile i.e a relative low toxicity for human and aquatic species.

Lab scale trials and formulation

Trials with 240 g/l Glyphosate (IPA salt) were performed on phytotronic chamber in ARD lab with several weed species. Spray retention and efficiency assessed by parallel-line technique were used as bioassay's parameters for the optimization of the final formulation. This method finally leads to a micro-emulsion with APP as optimized adjuvant.

The graph below shows how a glyphosate micro-emulsion was optimized.

The dose-response curve and it non-linear regression gives the efficacy parameter R for the treatment of Avena Fatua. A positive effect of adjuvant gives a R value greater than one and increases as this effect is large. In the next section, these results will be confirmed in the field.

Figure 2 : Bioassay on Avena Fatua. Dose-Response curve and effiency parameter R of different fomulations

Glyphosate formulation. Field trials

Results on monocotyledons

The first trials were performed in the field conditions during the autumn of 2009 in the east of France on common weeds (re-growth wheat, Lolium multiflorum, Bromus sterilis, Alopecurus myosuroides , Veronica agrestis ) with 55% infection.

Formulations including APP surfactants were compared with ethoxylated tallow amine formulation (Buggy S® from Phyteurop).

Page 3: New Glyphosate formulation with reduced impact for the ... · PDF fileNew Glyphosate formulation with reduced ... characteristics for agrochemicals formulations ... New Glyphosate

New Glyphosate formulation with reduced impact for the Environment

Uses of APP surfactants as the green adjuvants Cédric Ernenwein2, Sophie Leporini1, Philippe Kueneman3, Corine Lajoie3

Application Note N° 02

Route de Bazancourt - 51110 Pomacle, France - Tel.: +33 (0)3 26 88 84 10 – Fax: +33 (0)3 26 88 84 11 www.wheatoleo.com - [email protected]

Results hereafter are an average of 3 blocks and 3 repetitions.

First assessments at 11 days after treatment (11 DAT) and at lowest concentrations (2 L/ha) show a small difference between the green formulations and the traditional one.

After 21 days (21 DAT), there are non significant differences between the 3 formulations, all being very efficient.

Figure 3 : Efficiency for the treatments of common weeds

The 2nd

trial on vineyards (average of 2 trials) in the south of France (Haute-Garonne and Rhône) for the treatment of all weeds (Erigeron, Vulpia, Geranium rotundifolium, Crepis sancta, Sonchus sp. ) with a 57% infection, exhibits the higher performance of APP formulations versus the traditional one.

Figure 4 : Efficiency for the treatments of weeds of vineyards.

Results on dicotyledons This last graph shows the results (average of 3 blocks) for the treatment of the Veronica agrestis under inter culture conditions (after plowing). The percentage of infection was of 35%. At 2 or 3 l/ha the optimized APP formulation (2009) gives better results. These results confirm the previous studies performed in phytotronic chamber with plants in pots.

Page 4: New Glyphosate formulation with reduced impact for the ... · PDF fileNew Glyphosate formulation with reduced ... characteristics for agrochemicals formulations ... New Glyphosate

New Glyphosate formulation with reduced impact for the Environment

Uses of APP surfactants as the green adjuvants Cédric Ernenwein2, Sophie Leporini1, Philippe Kueneman3, Corine Lajoie3

Application Note N° 02

Route de Bazancourt - 51110 Pomacle, France - Tel.: +33 (0)3 26 88 84 10 – Fax: +33 (0)3 26 88 84 11 www.wheatoleo.com - [email protected]

Figure 5 : Efficiency for the treatment of Veronica agrestis

Ecotoxicological profile - biodegradability

Low toxicity for aquatics organisms and biodegradability are from now on the important criteria in the modern formulations, as well as human toxicity and regulatory status.

Letal concentration (LC50) after 48H of exposition was assessed on Daphnia Magna in ARD ecotoxicology lab.

LC 50 / 48H Buggly S ® 23 ppm Harmful

Formulation 2009 with APP 130 ppm Non toxic

Table 2 : Results of ecotoxicity tests on daphnia Magna

On the other hand, test performs with respect of OECD 301F guideline shows a level of biodegradability higher than 50% at 28 days with the formulation of glyphosate at 240 g/l with APP.

Conclusion With higher or similar results in crop treatment, an ecotoxicity six times lower than traditional formulation and a favorable biodegradability , the APP glyphosate formulations are a milestone for the agrochemical green formulations. The Appyclean surfactants range is proving to be a promising adjuvant for the development of all low environmental impact products.