Abstract
Several different types of cyclic phosphonates IVA-IVF and caged bicyclic phosphates IVG-IVH were further designed and synthesized. On the basis of systematic bioassay, several cyclic phosphonates were found to be effective against broadleaves by post-emergence application at 18.5~75 g ai/ha in the greenhouse.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Roy NK, Nidiry ES, Vasu K et al (1996) Quantitative structure-activity relationship studies of O, O-bisaryl alkylphosphonate fungicides by Hansch approach and principal component analysis. J Agric Food Chem 44:3971–3976
Forlani G, Giberti S, Berlicki L et al (2007) Plant P5C reductase as a new target for aminomethylenebisphosphonates. J Agric Food Chem 55:4340–4347
Forlani G, Occhipinti A, Berlicki Ł et al (2008) Tailoring the structure of aminobisphosphonates to target plant P5C reductase. J Agric Food Chem 56:3193–3199
Cox JM, Hawkes TR, Bellini P et al (1997) The design and synthesis of inhibitors of imidazoleglycerol phosphate dehydratase as potential herbicides. Pestic Sci 50:297–311
He HW, Wang J, Liu ZJ (1994) Synthesis of α-(substituted phenoxy acetoxy)alkyl phosphonates. Chinese Chem Lett 5:35–38
He HW, Wang J, Liu ZJ et al (1994) Study on biologically active organophosphorus compounds V, synthesis and properties of α-(substituted phenoxyacetoxy) alkyl phosphonates. Chin J Appl Chem 11:21–24
He HW, Wang J, Liu ZJ et al (1994) Studies on biologically active organphosphorus compounds. VI. Synthesis properties and biological activity of α-1-oxophosphonic acid derivatives. J Centr Chin Norm Univ (Nat Sci) 28:71–76
Chen T, Shen P, Li YJ et al (2006) Synthesis and herbicidal activity of O,O-dialkyl phenoxyacetoxyalkylphosphonates containing fluorine. J Fluorine Chem 127:291–295
Chen T, Shen P, Li Y et al (2006) The synthesis and herbicidal evaluation of fluorine-containing phenoxyacetoxyalkylphosphonate derivatives. Phosphorus Sulfur Silicon Relat Elem 181:2135–2145
Wang J, Chen XY, Liu XF et al (1999) The synthesis and biological properties of α-1-halogenated phenoxy carbonyloxy alkylphosphonic acids and esters. Chin J Chem Reag 21:301–303
He HW, Chen T, Li YJ (2007) Synthesis and herbicidal activity of alkyl 1-(3-trifluoromethylphenoxyacetoxy)-1-substituted methylphosphonates. J Pest Sci 32:42–44
Li YJ, He HW (2008) Synthesis and herbicidal activity of α-[2-(fluoro-substituted phenoxy) propionyloxy] alkyl phosphonates. Phosphorus, Sulfur Silicon Relat Elem 183:712–713
He HW, Liu ZJ, Wang J (1998) Synthesis and biological activities of α-1-[2-(2,4-dichlorophenoxy)propionyloxy] alkyl phosphonates. Chin J Appl Chem 15:88–90
Wang J, He HW, Liu ZJ (1997) Synthesis of α-[2-(2, 4-dichlorophenoxy) propionyloxy] alkyl phosphonates. Chin Chem Lett 8:943–944
Wang T, He HW (2004) Simple and improved preparation of α-oxophosphonate monolithium salts. Phosphorus, Sulfur Silicon Relat Elem 179:2081–2089
He HW, Yuan JL, Peng H et al (2011) Studies of O, O-dimethyl α-(2,4-dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex. J Agric Food Chem 59:4801–4813
Peng H, Wang T, Xie P et al (2007) Molecular docking and three-dimensional quantitative structure-activity relationship studies on the binding modes of herbicidal 1-(substituted phenoxyacetoxy) alkylphosphonates to the E1 component of pyruvate dehydrogenase. J Agric Food Chem 55:1871–1880
Wang T, He HW, Miao FM (2009) Synthesis, crystal structure and herbicidal activity of α-(2,4-dichlorophenoxyacetoxy)-α-arylmethylphosphonates. Chin J Org Chem 29:1152–1157
Meng LP, He HW, Liu ZJ (1998) Synthesis and biological activities of O,O-dimethyl α-(NO2 substituted phenoxyacetoxy)alkylphosphonates. Chin J Hubei Chem Industry (special issu):40–41
He HW, Peng H, Wang T et al (2013) α-(Substituted-phenoxyacetoxy)-α-heterocyclylmethylphosphonates: Synthesis, herbicidal activity, inhibition on pyruvate dehydrogenase complex (PDHc), and application as postemergent herbicide against broadleaf weeds. J Agric Food Chem 61:2479–2488
He HW, Meng LP, Hu LM et al (2002) Synthesis and plant growth regulatory activity of 1-(1-phenyl 1.2.4-triazole-3-oxyacetoxy)alkyl phosphonates. Chin J Pest Sci 4:14–18
Kiran YB, Reddy CD, Gunasekar D et al (2008) Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates. Eur J Med Chem 43:885–892
Sulsky R, Robl JA, Biller SA et al (2004) 5-Carboxamido-1,3,2-dioxaphosphinanes, potent inhibitors of MTP. Bioorg Med Chem Lett 14:5067–5070
Patel DV, Rielly-Gauvin K, Ryono DE (1990) Peptidic α-hydroxy phosphinyls C-terminal modification methodology. Tetrahedron Lett 31:5591–5594
Stowasser B, Budt K-H, Jian-Qi L et al (1992) New hybrid transition state analog inhibitors of HIV protease with peripheric C2-symmetry. Tetrahedron Lett 33:6625–6628
Sikorski JA, Miller MJ, Braccolino DS et al (1993) EPSP synthase: The design and synthesis of bisubstrate inhibitors incorporating novel 3-phosphate mimics. Phosphorus, Sulfur Silicon Relat Elem 76:115–118
Engel R (1977) Phosphonates as analogues of natural phosphates. Chem Rev 77:349–367
Allen MC, Fuhrer W, Tuck B et al (1989) Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J Med Chem 32:1652–1661
Smith WW, Bartlett PA (1998) Macrocyclic inhibitors of penicillopepsin. 3. Design, synthesis, and evaluation of an inhibitor bridged between P2 and P1’. J Am Chem Soc 120:4622–4628
Allen J, Atherton F, Hall M et al (1978) Phosphonopeptides, a new class of synthetic antibacterial agents. Nature 272:56–58
Atherton FR, Hassall CH, Lambert RW (1986) Synthesis structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl) phosphonic acid and (aminomethyl) phosphonic acid. J Med Chem 29:29–40
Jennings LJ, Macchia M, Parkin A (1992) Synthesis of analogues of 5-iodo-2′-deoxyuridine-5′-diphosphate. J Chem Soc Perkin Trans 1:2197–2202
Patel DV, Rielly-Gauvin K, Ryono DE (1990) Preparation of peptidic α-hydroxy phosphonates a new class of transition state analog renin inhibitors. Tetrahedron Lett 31:5587–5590
Lavielle G, Hautefaye P, Schaeffer C et al (1991) New α-amino phosphonic acid derivatives of vinblastine: chemistry and antitumor activity. J Med Chem 34:1998–2003
Alonso E, Alonso E, Solís A et al (2000) Synthesis of N-alkyl-(α-aminoalkyl) phosphine oxides and phosphonic esters as potential HIV-protease inhibitors, starting from α-aminoacids. Synlett 2000:698–700
Camp NP, Hawkins PCD, Hitchcock PB et al (1992) Synthesis of stereochemically defined phosphonamidate-containing peptides: inhibitors for the HIV-1 proteinase. Bioorg Med Chem Lett 2:1047–1052
Hirschmann R, Smith AB, Taylor CM et al (1994) Peptide synthesis catalyzed by an antibody containing a binding site for variable amino acids. Science 265:234–237
Bischofberger N, Waldmann H, Saito T et al (1988) Synthesis of analogs of 1,3-dihydroxyacetone phosphate and glyceraldehyde 3-phosphate for use in studies of fructose-1,6-diphosphate aldolase. J Org Chem 53:3457–3465
Allen MC, Fuhrer W, Tuck B et al (1989) Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond. J Med Chem 32:1652–1661
Palacios F, Alonso C, de los Santos JM (2005) Synthesis of β-aminophosphonates and-phosphinates. Chem Rev 105:899–932
Pudovik A, Konovalova I (1979) Addition reactions of esters of phosphorus (III) acids with unsaturated systems. Synthesis 1979:81–96
Ten Hoeve W, Wynberg H (1985) The design of resolving agents. Chiral cyclic phosphoric acids. J Org Chem 50:4508–4514
Kumaraswamy S, Selvi RS, Swamy KK (1997) Synthesis of new α-hydroxy-, α-halogeno- and vinylphosphonates derived from 5,5-dimethyl-1,3,2-dioxaphosphinane-2-one. Synthesis 1997:207–212
Zuo N, He HW (2006) 2-[(4-Chlorophenyl) hydroxymethyl]-5, 5-dimethyl-4-phenyl-1, 3, 2-dioxaphosphinane-2-one. Acta Cryst E62:o4864–o4865
Chen T, Shen P, Li Y et al (2006) Synthesis and herbicidal activity of O, O-dialkyl s containing fluorine. J Fluorine Chem 127:291–295
Brayer JL, Talinani L (1990) Tessier J (1990) Preparation of aryl and aryl oxyacetyl diaineoalkanes and analogs as agrochemical fungicides. EP 376:819
Wang W, He HW, Zuo N et al (2012) Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2- dioxaphosphinane-2-one containing fluorine. J Fluorine Chem 142:24–28
Wang W, He HW, Zuo N et al (2012) Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinane-2-one. J Agric Food Chem 60:7581–7587
Xie Q, Zheng J (1991) Synthesis and structure of tricyclohexylstannane aromatoxyacetares. Chin J Org Chem 11:82–87
Zuo N, He HW (2007) 2-{(2-Chlorophenyl)[(2,4-dichlorophenoxy) acetoxy] methyl}-5, 5-dimethyl-1,3,2-dioxaphosphinane-2-one. Acta Cryst E63:o794–o795
Verkade J, Reynolds L (1960) The synthesis of a novel ester of phosphorus and of arsenic. J Org Chem 25:663–665
Rätz R, Sweeting OJ (1965) 4-Hydroxymethyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane 1-sulfide and derived compounds. J Org Chem 30:438–442
Rätz R (1965) Bicyclic phosphorus-containing carbamates US patent 3,168,549, 2 Feb 1965
Rätz R (1966) US patent 3,287,448, 1966
Hechenbleikner I, Lanoue FC, Pause CW et al (1966) US patent 3,293,327, 20 Dec 1966
Bowery N, Collins J, Hill R (1976) Bicyclic phosphorus esters that are potent convulsants and GABA antagonists. Nature 261:601–603
Toy DF, Walsh N (1987) Phosphorus chemistry in everyday living. American Chemical Society, Washington, DC, p 317
Ozoe Y, Mochida K, Eto M (1982) Reaction of toxic bicyclic phosphates with acetylcholinesterases and α-chymotrypsin. Agric Biol Chem 46:2527–2531
Li YG, Wang JJ, Han T (1988) Study of caged bicyclic phosphates I: 1-Oxo-4-substituted-2,6,7-trioxa-1-phosphabicyclo[2,2,2]octane and its reactions. Acta Chim Sinica 46:679–685
Li YG, Wang JJ, Liu YS (1989) Study of caged bicyclic phosphates (II)-synthesis of derivatives of 1-sulfo-1-phospha-4-methylene-2,6,7-trioxabicyclo[2,2,2]octane. Chem J Chin Univ 10:1002–1006
Shao RL, Wang SP, Wang DZ (1991) Studies on synthesis and biological activity of caged bicyclophosphate compounds. Chem J Chin Univ 12:1063–1065
Li YG, Li JM, Ren HL et al (1992) Studies of caged bicyclic phosphates (V) Synthesis of 1-oxo-1-phospha-2,6,7-trioxabicyclo[2,2,2]-4-substituted carbonyl octane. Chem J Chin Univ 13:204–208
Li YG, Wang XL, Zhu XF et al (1995) Study on the synthesis of 1-sulfur-1-phospha-2,6,7-trioxzbicyclo [2.2.2] octyl-4-methyl thioethers and its sulfoxides. Chin J Org Chem 15:57–60
Li YG, Zhu XF, Huang Q et al (1996) Studies on the Synthesis and Structure of N-(1-Oxo-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane-4-carbonyl)-N’-aryl(alkyl)thioureas. Chem J Chin Univ 17:1394–1398
Vyverberg FJ, Chapman RW (2002) Process for the production of pentaerythritol phosphate alcohol US Patent 6,455,722, 24 Sep, 2002
Sheng XJ, He HW (2006) 4-[(2-Chloro-5-methylphenoxy)acetoxymethyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide. Acta Cryst E62:o4398–o4399
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
Copyright information
© 2014 Chemical Industry Press, Beijing and Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
He, HW., Peng, H., Tan, XS. (2014). Cyclic Phosphonates and Caged Bicyclic Phosphates. In: Environmentally Friendly Alkylphosphonate Herbicides. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-44431-3_5
Download citation
DOI: https://doi.org/10.1007/978-3-662-44431-3_5
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-44430-6
Online ISBN: 978-3-662-44431-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)