Chitosan Polymers and Plant Extracts to Develop Biofungicides

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Chitosan Polymers and Plant Extracts to Develop Biofungicides THÈSE PRÉSENTÉE POUR OBTENIR LE GRADE DE DOCTEUR DE L’UNIVERSITÉ DE BORDEAUX ÉCOLE DOCTORALE DES SCIENCES CHIMIQUES DE BORDEAUX SPÉCIALITÉ POLYMÈRES Anne LORON Chitosan polymers and plant extracts to develop biofungicides Sous la direction de Véronique COMA Soutenue le 26 janvier 2021 Membres du jury : M. CATHALA Bernard Directeur de recherche, INRAe Nantes Rapporteur M. MOUNIER Jérôme Professeur, LUBEM, Université de Brest Rapporteur Mme FORGET Florence Directrice de recherche, INRAe Bordeaux Examinatrice M. PERUCH Frédéric Directeur de recherche CNRS, Université de Bordeaux Président M. TABARY Nicolas Maître de conférences, UMET, Université de Lille Examinateur Mme COMA Véronique Maître de conférences HDR, Université de Bordeaux Directrice de thèse What we know is a drop, what we don't know is an ocean. Isaac NEWTON REMERCIEMENTS Je souhaiterais remercier Sébastien Lecommandoux ainsi que Henri Cramail de m’avoir permis d’effectuer ma thèse au Laboratoire de Chimie des Polymères Organiques au sein de l’équipe 2. Je remercie Véronique Coma de m’avoir permis de réaliser ce travail de thèse pendant trois ans, de m’avoir laissé de la liberté dans le projet tout en restant disponible lorsque j’en avais besoin. Merci d’avoir pris le temps de minutieusement préparer les présentations orales, même si ces répétitions n’étaient pas mes moments favoris. Un grand merci à Christian pour le soutien technique, précis, discret mais considérable. Je tiens à remercier Frédérique Ham-Pichavant pour son attention et son efficacité particulièrement appréciable au N0. Je remercie également Nicolas Tabary de m’avoir accueillie au laboratoire UMET à Lille et accompagnée. Mes remerciements vont aussi à Vessela Atanasova pour son aide, ses conseils et les discussions scientifiques ou personnelles tout au long de la thèse. J’ai beaucoup apprécié travailler dans d’autres laboratoires, où j’ai toujours été bien accueillie et encadrée. I also thank Ramunė Rutkaitė, Vesta Navikaitė- Šnipaitienė and Deimantė Rosliuk for their help and the intresting discussions we had. I particularly thank Ramunė for her understanding and kindness. J’aimerais remercier les « anciens » : Coralie, David, Élodie, Fiona, Hélène, Imane, Lauriane, Leila, Marie, Michlèle, Nadia, Quentin S., Stéphanie et Sylwia et plus particulièrement Christopher, Martin C., Erwan, Fiona, Florian B., Guillaume et Pauline... et les « actuels » : Anouk, Assia, Chloé, Clémence, Diana, Dijwar, Fanny, Hanaé, Laurine, Léa, Martin F., Megi, Mostafa, Nadia, Pablo, Paul, Pedro, Péroline, Peter, Pierre, Romane, Samir, Thaíssa, Tingting, Tim, Vaïana et Valentin. Merci à Anderson pour sa constante gentillesse, à Victor et Margaux pour l’escalade et leur sympathie : ) et à Cédric C., l’oreille attentive. Je remercie Yunhui pour son aide et son endurance ainsi que Sylvain, le semi-permanent. Je remercie particulièrement le groupe unique (et leur +1 respectifs) : Bobi, Jamais203, Mashur, Gavroch, Chaton-Guerrier et Le Maître Pokémon. Boris, pour sa compréhension et son ouverture d’esprit. Flo, pour son attention et sa perspicacité. Manon, pour sa franchise et son dynamisme. Jamie, pour sa générosité et son soutien. Jessie, pour sa capacité à s’émerveiller et sa force de caractère. Jérémy, pour son abnégation et son exemplarité. Je remercie également toute ma famille, en particulier mon frère et ma sœur, pour la bienveillance spontanée de notre relation et mes parents, pour leur confiance, leur réconfort et leur soutien constant. Je remercie Romain du fond du cœur. V VI TABLE OF CONTENTS REMERCIEMENTS ................................................................ V TABLE OF CONTENTS ......................................................... VII TABLE OF ABBREVIATIONS .................................................. XV TABLE OF SYMBOLS ......................................................... XVII RESUME EN FRANÇAIS ...................................................... XIX GENERAL INTRODUCTION...................................................... 1 CHAPTER I – BIOFUNGICIDES: NECESSITY & PRODUCTION ............... 5 1 Fungal diseases of maize and wheat and their treatments ............................. 6 1.1 General diseases caused by Fusarium spp. ......................................................... 6 1.2 Fusarium graminearum infection ........................................................................ 6 1.3 Mycotoxins produced by F. graminearum .......................................................... 8 1.3.1 Chemical structure .................................................................................... 8 1.3.2 Effects on animals and plants..................................................................... 9 1.3.3 TCTs in the food chain .............................................................................. 9 1.4 Management of F. graminearum on crops ........................................................ 10 1.4.1 Agronomic practices ............................................................................... 10 1.4.2 Use of antagonistic microorganims .......................................................... 11 1.4.3 Traditional synthetic or bio-based fungicides ............................................ 11 1.4.3.a Traditional synthetic fungicides ............................................................ 11 1.4.3.b Bio-based options suitable for organic farming ....................................... 12 1.4.4 Global management ................................................................................ 13 1.5 Concluding remarks ...................................................................................... 14 2 Chitosan: an active biopolymer with antifungal and elicitor properties ......... 14 2.1 Generalities on chitosans ............................................................................... 14 2.1.1 Structure, origin and elaboration process .................................................. 14 2.1.2 Specific characterisation of MW and DD ................................................. 15 2.2 Specific antimicrobial properties of chitosans ................................................. 16 2.2.1 Modes of action: what we know so far ..................................................... 16 2.2.2 Impact of some physicochemical parameters on antimicrobial properties ... 18 VII 2.3 Some applications of chitosan........................................................................ 19 2.3.1 Different formulations depending on the application................................. 19 2.3.2 Specific applications for pest control on crops ........................................... 20 2.3.2.a Antifungal effects ................................................................................. 20 2.3.2.b Eliciting properties ............................................................................... 22 2.3.2.c Two other beneficial effects on the plant ................................................ 24 2.4 Concluding remarks ...................................................................................... 24 3 Plant extracts: active molecules with antifungal and antioxidant properties ... 25 3.1 Plant extracts ................................................................................................ 25 3.1.1 Three principal classes of plant extracts .................................................... 25 3.1.2 Extraction processes ................................................................................ 26 3.1.3 Properties of plant extracts ...................................................................... 27 3.1.3.a Lipophilic properties linked with the antifungal action ........................... 28 3.1.3.b Intrinsic antioxidant properties ............................................................. 29 3.2 Phenolic compounds from plant extracts ........................................................ 31 3.2.1 Structure of phenolic compounds ............................................................. 31 3.2.2 Properties of interest of phenolic compounds ............................................ 32 3.2.2.a Antifungal actions ................................................................................ 32 3.2.2.b Antimycotoxigenic action and antioxidant properties............................. 33 3.3 Specific case of tetrahydrocurcumin ............................................................... 34 3.3.1 A curcumin derivative ............................................................................. 34 3.3.2 Anti-microbial properties ......................................................................... 36 3.4 Concluding remarks ...................................................................................... 37 4 Encapsulation techniques of poorly water-soluble compounds .................... 37 4.1 What is encapsulation? .................................................................................. 38 4.2 Characterization of particles .......................................................................... 39 4.3 Physical entrapment ...................................................................................... 40 4.3.1 Spray-drying ........................................................................................... 40 4.3.2 Freeze-drying .......................................................................................... 42 4.3.3 Other physical techniques ........................................................................ 42 4.4 Encapsulation through physicochemical interactions
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