The Crystal and Molecular Structure of N-(Phosphonomethyl)glycine (Glyphosate).

Knuuttila, Pekka; Knuuttila, Hilkka; Nishida, Toshiaki; Enzell, Curt R.; Åkeson, Åke; Lundquist, Gunilla

doi:10.3891/acta.chem.scand.33b-0623

Cited by 44 publications

(42 citation statements)

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“…Glyphosate exists as a zwitterion. 7 The acid dissociation constants for glyphosate are pKa 1 0.8 (first phosphonic), pKa 2 2.3 (carboxylic), pKa 3 6.0 (second phosphonic), and pKa 4 11 (amine). Further, the carboxyl and phosphonyl groups are electrophilic, while the amino group is nucleophilic, while the double-bonded and deprotonated oxygens of the phosphonyl group are stabilized by delocalization, resulting in the phosphonyl group being less susceptible to a nucleophilic attack than the carboxyl group.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate

et al. 2007

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The synthesis of new acrylate and methacrylate derivatives of a glyphosate is reported. Two isomers resulting from a hindered rotation around the amide C-N bond are observed for both acrylic and methacrylic analogs, and barriers for internal rotation are obtained. Biological activity tests indicate that functionalized glyphosates possess herbicidal activity similar to that of the parent compound. Only the acrylated glyphosate derivatives undergo photopolymerization. The resulting photopolymer of acrylated glyphosate retains the biological activity. The methacrylated glyphosates are unreactive. Differential reactivity is explained by the different conformational preferences of the functionalized glyphosates. The experimental findings are supported by the results of density functional theory geometry optimizations.

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate

et al. 2007

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“…Essas diferenças estruturais refletem diretamente na eficácia do produto final, visto que o polimorfismo altera as características físico-químicas do composto mudando a maneira como ele interage no meio biológico. É necessário o controle de qualidade da matéria-prima utilizada, do controle de temperatura e da umidade no meio em que é produzido o produto final e seu posterior armazenamento para que seja evitada a presença de um polimorfo e não da estrutura comercial no produto final [24][25][26][27][28] .…”

Section: Utilização De Agrotóxicosunclassified

“…A primeira estrutura cristalina [Figura 1 -estrutura (a)] desse composto encontrada no CCDC foi apresentada pelos pesquisadores finlandeses Pekka Knuuttila e Hilkka Knuuttila em 1979, cuja amostra de glifosato utilizada foi isolada a partir do produto Roundup® e recristalizada com água quente, com o cristal obtido foi realizado a coleta de dados por meio da difração de raios X para determinação da estrutura cristalina e molecular. Segundo os autores, esse trabalho visava entender o comportamento desse composto como herbicida e sua decomposição metabólica 26 [26][27][28] .…”

Section: Utilização De Agrotóxicosunclassified

Legislação e Normatização para o Glifosato no Brasil

2019

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Os agrotóxicos, no regime da propriedade intelectual, podem ser classificados como novas moléculas ou princípios ativos passíveis de serem patenteados. Os Tratados, Convenções e Acordos Internacionais estabelecidos entre diversos países visam à convergência de interesses de cooperação econômica para proteção às invenções. O glifosato é o herbicida mais vendido do mundo. A diferentes estruturas cristalinas da molécula glifosato (polimorfismo) permitiram o depósito de distintos registros de patentes. A evolução histórica do sistema internacional de patentes e da legislação interna para agrotóxicos permitem a análise dos registros do herbicida glifosato.

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“…This small molecule contais both donor (acidic) and acceptor (basic) functional groups with pKa 10.9, 5.9 and 2.3, respectivelly. Glyphosate can form a zwitterionic structure (Knuuttila and Knuuttila, 1979). This is reflected in very good water solubility (11.6 g/L at 25 °C) and poor solubility in organic solvents (Subramaniam et al, 2000).…”

Section: Chemistrymentioning

confidence: 99%

Is Glyphosate Really Hazardous for Human Health?

Patočka¹

2018

Mil. Med. Sci. Lett.

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Glyphosate [N-(phosphonomethyl) glycine] is one the world's most widely used agricultural herbicide. It allows farmers to spray a planted field, generally before the crops have sprouted, killing weeds but not the crops that will grow there. GMO critics claim glyphosate is linked to autism, cancer, gluten allergies, 'leaky gut' syndrome and other disorders. Concerns about glyphosate's possible health impacts increased in 2015 after the International Agency for Research on Cancer, a research arm of the World Health Organization, classified glyphosate as "probably carcinogenic". The ecological risk assessment indicates that there is potential for effects on birds, mammals, and terrestrial and aquatic animals. A joint panel from the World Health Organization and the Food and Agriculture Organization of the United Nations issued an summary evaluation of glyphosate in May 2016, concluding it poses no cancer risks as encountered in food and does not impact our genes. Although the European Food Safety Authority declared the evidence on glyphosate's carcinogenicity for humans to be "very limited", there is still some doubt as to whether all the studies have been made "lege artis" or whether they have not even been falsified.

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The Crystal and Molecular Structure of N-(Phosphonomethyl)glycine (Glyphosate).

Cited by 44 publications

References 0 publications

Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate

Synthesis and Biological Activity of Photopolymerizable Derivatives of Glyphosate

Legislação e Normatização para o Glifosato no Brasil

Is Glyphosate Really Hazardous for Human Health?

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