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Glufosinate (Phosphinothricin), A Natural Amino Acid with Unexpected Herbicidal Properties

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Reviews of Environmental Contamination and Toxicology

Part of the book series: Reviews of Environmental Contamination and Toxicology ((RECT,volume 138))

Abstract

In addition to the large number of phosphates formed under natural conditions, such as the nucleotides and phospholipids, the world of living organisms also presents a small group of phosphonic acids, the structure of which was first brought to light during the last 20 years or so. One of the first compounds from this series was 1,2-epoxipropanephosphonic acid, which was isolated from protozoa in 1969 and is known by the trivial name fosfomycin (1) (Christensen et al. 1969; Hendlin et al. 1969). Other examples are plumbemycin (2) (Park et al. 1977), isolated in 1976 from cultured filtrates of Streptomyces plumbeus, and fosmidomycin (3) (Kuroda et al. 1980), isolated from Streptomyces lavendulae. All three of these have an antibiotic effect (Fig. 1). Natural substances containing a phosphinic acid moiety in which the phosphorus atom is bound to two carbon atoms were unknown 20 years ago.

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References

  • Acaster MA, Weitzmann PDJ (1985) Kinetic analysis of glutamine synthetases from various plants. FEBS Lett 189:241–244.

    Article  CAS  Google Scholar 

  • Afzali-Ardakani A, Rapoport H (1980) L-Vinylglycine. J Org Chem 45:4817–4820.

    Article  CAS  Google Scholar 

  • Arvidsson T (1986) New herbicides in potato. Rept 27th Swed Weed Conf 1:257–272.

    Google Scholar 

  • Bahat A (1985) Glufosinate ammonium for general weed control in vineyards, citrus, and other fruit orchards and uncultivated areas. Phytoparasitica 13:239.

    Google Scholar 

  • Baillie AC, Wright BJ, Wright K, Earnshaw CG (1981) Derivatives of 4-(methylphosphinyl)-2-oxobutanoic acid, herbicidal composition containing them and their intermediates. Eur Pat Appl EP 30 424 Fisons Ltd; Chem Abstr 1981, 95, P 204152x.

    Google Scholar 

  • Baldwin JE, Haber SH, Hoskens C, Kruse LK (1977) Synthesis of β,γ-unsaturated amino acids. J Org Chem 42:1239–1241.

    Article  PubMed  CAS  Google Scholar 

  • Balthazor TM, Flores RA (1980) Dipolar cycloadditions of an acetylenic phosphinate. J Org Chem 45:529–531.

    Article  CAS  Google Scholar 

  • Bartsch K, Dichmann R, Schmitt P, Uhlmann E, Schulz A (1990) Stereospecific production of the herbicide phosphinothricin by transamination: Cloning, characterization, and overexpression of the gene encoding a phosphinothricin-specific transaminase from Escherichia coli. Appl Environ Microbiol 56:7–12.

    PubMed  CAS  Google Scholar 

  • Bayer E, Gugel KH, Haegele K, Hagenmaier H, Jessipow S, Koenig WA, Zaehner H (1972) Phosphinothricin und phosphinothricyl-alanyl-alanin. Helv Chim Acta 55:224–239.

    Article  PubMed  CAS  Google Scholar 

  • Beckerson DW, Townsend D, Hay G (1985) Potato top-growth desiccation using glufosinate ammonium. Res Rept Expert Comm Weeds East Can Annu 30: 412.

    Google Scholar 

  • Bellinder RR, Chabot JF (1986) Scanning electron microscopy of leaf surfaces treated with glufosinate ammonium. Weed Sei Soc Am 26:104–105.

    Google Scholar 

  • Bier B, Langelueddeke P, Schumacher H (1988) Unkrautbekaempfung in Kartoffeln—ein neues Einsatzgebiet fuer Basta®. Mitteilung Biol Bundesanstalt Land-, Forstwirtschaft Nr. 245:245–246.

    Google Scholar 

  • Block HD (1976a) Phosphorus-containing aldehydes. Germ Offen DE 2 516 341 Bayer AG; Chem Abstr 1977, 86, 55580v.

    Google Scholar 

  • Block HD (1976b) Phosphorus-containing aldehydes diaeylates. Germ Offen DE 2 516 343 Bayer AG; Chem Abstr 1977, 86, 55581w.

    Google Scholar 

  • Block HD (1982) Phosphorigsaeure-chlorid-dimethylester. In: Regitz M (ed), Houben-Weyl Methoden der organ Chemie. Thieme, Stuttgart. Vol E1: 375.

    Google Scholar 

  • Blumenfeld T, Kleifeld Y, Bucsbaum H, Funk AS (1988) Weed control in cotton planted directly into the stubble of wheat or legumes. Phytoparasitica 16:398.

    Google Scholar 

  • Boeshar M, Erpenbach H, Jaegers E, Kleiner HJ, Koll HP (1990) Verfahren zur Herstellung von N-Acyl-phosphinothricindiestern. Eur Pat Appl EP 350 694 Hoechst AG; Chem Abstr 1990 113:41329j.

    Google Scholar 

  • Botterman J (1989) Advances in engineering herbicide resistance in plants. Brit Crop Prot Conf Weeds 979–985.

    Google Scholar 

  • Botterman J, Leemans J (1989) Discovery, transfer to crops, expression and biological significance of a bilaphos resistance gene. Brit Crop Prot Conf Weeds Mo- nogr 42:63–68.

    CAS  Google Scholar 

  • Botterman J, D’Halluin K, De Greef W, Leemans J (1991) Engineering of glufosinate resistance and evaluation under field conditions. Long Ashton Int Symp Meet 11: 355–363.

    Google Scholar 

  • Bucsbaum H, Horowith M, Kleifeld Y, Herzlinger G, Bargutti, A (1985) Experi-ments on the control of phragmites in drainage canals. Phytoparasitica 13:249–250.

    Google Scholar 

  • Buebl W, Koecher H, Langelueddeke P (1990) Versuche zur Vertraeglichkeit von Basta® in Sonderkulturen. Z Pflanzenkrankh Pflanzenschutz Sonderheft 12:537–547.

    Google Scholar 

  • Caldwell CD (1983) Effect of glufosinate ammonium as a desiccant for Tobin rapeseed. Effect of glufosinate ammonium as a desiccant for Altex. Res Rept Expert Comm Weeds West Can 1:263.

    Google Scholar 

  • Christensen BG, Leanza JW, Beattie TR, Patchett AA, Arison BH, Ormond RF, Kuehl FA, Albers-Shongerg G, Jardetzky O (1969) Phosphonomycin: Structure and synthesis. Science 166:123.

    CAS  Google Scholar 

  • Coffee Research Foundation Kenya Coffee (1990) Weed control in coffee. 55:837–840.

    Google Scholar 

  • De Block M, Botterman J, Vandewiele M, Dockx T, Thoen C, Gossel V, Mowa NR, Thompson C, Van Montagu M, Leemanns J, (1987) Engineering herbicide resistance in plants by expression of a detoxifying enzyme. EMBO J 6:2513–2518.

    PubMed  CAS  Google Scholar 

  • De Greef W, Delon R, De Block M, Leemans J, Botterman J (1989) Evaluation of herbicide resistance in transgenic crops under field conditions. Biotechnology 7: 61–64.

    Article  Google Scholar 

  • Delmonte Research and Hoechst Philippines (1989) Evaluation of Basta® 20 SL, Roundup® 36 EC, Gramoxone® 24 EC and Gramoxone®/Karmex® for weed control in established banana plantation (unpublished).

    Google Scholar 

  • Devine MD, Holm FA, Clayton RE (1989) Efficacy of various desiccants on flax. Res Rept Expert Comm Weeds West Can 2:823–824.

    Google Scholar 

  • Donn G (1982) Der Einfluss von Klimafaktoren auf die herbizide Wirkung von Glufosinat ammonium. Med Fac Landbouw Rijsuniv Gent 47:105–110.

    Google Scholar 

  • Donn G, Tischer E, Smith J, Goodman H (1984) Herbicide-resistant alfalfa cells: An example of gene amplification in plants. J Mol Appl Genet 2:621–635.

    PubMed  CAS  Google Scholar 

  • Donn G, Dirks R, Eckes P, Uijtewaal B (1990a) Transfer and expression of modified phosphinothricin-acetyltransferase gene from Streptomyces viridichromogenes in tomato, melon, carrot, and strawberry. Abstr VII Int Congr Plant Tissue Cell Cult Amsterdam: 176.

    Google Scholar 

  • Donn G, Nilges M, Morocz S (1990b) Stable transformation of maize with a chimaeric, modified phosphinothricin-acetyltransferase gene from Streptomyces viridochromogenes. Abstr VII Int Congr Plant Tissue Cell Cult Amsterdam: 53.

    Google Scholar 

  • Donn G, Eckes P (1992) Basta®—vertraegliche Kulturpflanzen durch Uebertragung eines synthetischen Phosphinothricin-Acetyltransferase-Gens. Z Pflanzenkrankh Pflanzenschutz, Sonderheft 13:499–504.

    Google Scholar 

  • Dorn E, Goerlitz G, Heusei R, Stumpf K (1992) Verhalten von Glufosinat-ammonium in der Umwelt—Abbau und Einfluss auf das Oekosystem. Z Pflanzenkrankh Pflanzenschutz, Sonderheft 13:459–468.

    Google Scholar 

  • Ebert E, Leist KH, Mayer D (1990) Summary of safety evaluation toxicity studies of glufosinate ammonium. Food Chem Toxicol 28:339–349.

    Article  PubMed  CAS  Google Scholar 

  • Eckes P, Donn G, Wengenmayer F (1987) Genetic engineering with plants. Ang Chem Int Ed Engl 26:382–402.

    Article  Google Scholar 

  • Eckes P, Schmitt P, Daub W, Wengenmayer F (1989a) Overproduction of alfalfa glutamine synthetase in transgenic tobacco plants. Mol Gen Genet 217:263–268; Chem Abstr 1989, 111, 72466q.

    Article  CAS  Google Scholar 

  • Eckes P, Uijtewaal B, Donn G (1989b) Synthetic gene confers resistance against the broad spectrum herbicide L-phosphinothricin in plants. J Cell Biochem 13D:334.

    Google Scholar 

  • Entz PJ, Mazinke M, Wright EB (1989) To evaluate the efficacy of glufosinate ammonium in the desiccation of sunflowers. Res Rept Expert Comm Weeds West Can 2:825.

    Google Scholar 

  • FAO/WHO (1991) Pesticide residues in food, Toxicology evaluation. Report of the Joint Meeting of the FAO Panel of Experts on Pesticide Residues in Food and the Environment and the WHO Expert Group on Pesticide Residues. JMPR 209–239. World Health Organization of the United Nations, Geneva, 1992.

    Google Scholar 

  • Finke M, Muendnich R (1980) Phosphorus-containing cyanohydrinderivatives. Germ Offen DE 2 849 003 Hoechst AG; Chem Abstr 1981, 94, 121709n.

    Google Scholar 

  • Fischer HP (1990) Naturstoffsynthesen im Pflanzenschutz. Nachr Chem Techn Lab 38:732–740.

    Google Scholar 

  • Foster KR, O’Sullivan PA (1984) Efficacy of glufosinate ammonium as a desiccant for Tobin and Candle. Res Rept Expert Comm Weeds West Can 1:317–318.

    Google Scholar 

  • Gonzalez-Moro MB, Lacuesta M, Munoz-Rueda A, Becerril-Soto JM, Gonzalez-Murua C (1990) Effect of phosphinothricin on nitrogen metabolism in Zea mays. Plant Physiol 93(1) Suppl: 151.

    Google Scholar 

  • Grabley S, Sauber K (1982) Verfahren zur enzymatischen Herstellung von L-2- Amino-4-methylphosphinobuttersaeure. Germ Offen DE 3 048 612 Hoechst AG; Chem Abstr 1982, 97, 125725z.

    Google Scholar 

  • Gross H, Gnauk Th (1976) Eine einfache Synthese fuer D,L-Phosphinothricin. J Prakt Chem 318:157–160.

    Article  CAS  Google Scholar 

  • Gruszecka E, Mastalerz P, Soroka M (1975) New synthesis of phosphinothricin and analogs. Rocz Chemii 49:2127–2128; Chem Abstr 1976, 85, 5777y.

    CAS  Google Scholar 

  • Gruszecka E, Soroka M, Mastalerz P (1979a) Phosphonic analogs of α-methylaspartic- and α-methylglutamic acids. Pol J Chem 53:2327–2331; Chem Abstr 1980, 93, 8479d.

    CAS  Google Scholar 

  • Gruszecka E, Soroka M, Mastalerz P (1979b) Preparation of A ¿-phosphinothricin by Strecker reaction. Pol J Chem 53:937–939; Chem Abstr 1979, 91, 141198m.

    CAS  Google Scholar 

  • Gruszecka E, Masterlerz P, Soroka M. (1980) 2-Amino-4-(methylphosphinyl)butyric acid. Pol 105 240 (1980); Chem Abstr 1981, 95, 98025w.

    Google Scholar 

  • Hanessian St, Sahoo SP (1984) A novel and efficient synthesis of L-vinylglycine. Tetrahedron Lett 25:1425–1428.

    Article  Google Scholar 

  • Hendlin D, Stapley EO, Jackson M, Wallick H, Miller AK, Wolf FJ, Miller TW, Chaiet L, Kahan FM, Foltz EL, Woodruff HB, Mata JM, Hernandez S, Mochales S (1969) Phosphonomycin, a new antibiotic produced by strains of Streptomyces. Science 166:122.

    Article  PubMed  CAS  Google Scholar 

  • Henninger CC, Keeling JW, Abernathy JR (1989) Horseweed Conyza canadensis. Control in conservation tillage systems. Abstr Meet Weed Sei Soc Am 29:12–13.

    Google Scholar 

  • Herold A, Wendler C, Wild A (1990) The effect of phosphinothricin on glutathione synthesis in plants. Botanica Acta 103:68–71.

    CAS  Google Scholar 

  • Hess D (1992) Biotechnologie der Pflanzen, First Ed. Eugen Ulmer, Stuttgart, pp 256–258.

    Google Scholar 

  • Hidaka T, Imai S, Hara O, Anzai H, Murakami T, Nagaoka K, Seto H (1990) Carboxyphosphonoenolpyruvate phosphonomutase, a novel enzyme catalyzing C-P bond formation. J Bacteriol 172:3066–3072.

    PubMed  CAS  Google Scholar 

  • Hirose K (1988) Weed control in citrus growes. Jpn Pestic Inf 52:3–5.

    Google Scholar 

  • Hoechst AG (1990) Basta® and Dropp®: Partners for cotton defoliation and reduced regrowth. (unpublished).

    Google Scholar 

  • Hoechst Canada Inc Agriculture Div (1993) Glufosinate Ammonium Tolerant Canola, Hoechst Canada, Regina, Saskatchewan, pp 4–6.

    Google Scholar 

  • Hoechst Celanese Corp (1988) EUP-trials in non-crop conditions, no-till seed bed trials, postdirected trials (unpublished).

    Google Scholar 

  • Hoechst Columbiana SA (1988) Basta® against various weeds in different crops under different conditions (unpublished).

    Google Scholar 

  • Hoechst Ecuador SA (1985) Basta® for weed control in banana plantations in a long-term trial (unpublished).

    Google Scholar 

  • Hoechst Japan Ltd (1987) Control of Oenanthe javanica with Basta® prior to plowing (unpublished).

    Google Scholar 

  • Hoechst Pakistan Ltd (1990) To test the efficacy of Basta® 20 SL with the comparison of Stomp® in cotton crop, when sprayed at postemergence stage (unpublished).

    Google Scholar 

  • Hoechst Roussel USA (1989) Ignite® (GLA) in combination with Dropp® for cotton harvest aid (unpublished).

    Google Scholar 

  • Hoechst Roussel USA (1990) Ignite® (GLA) cotton defoliation (unpublished).

    Google Scholar 

  • Hoechst Taiwan (1987) Trial report of Basta® 20% SL against weeds on paddy dike (unpublished).

    Google Scholar 

  • Hoepfer M, Reifferscheid G, Wild A (1988) Molecular composition of glutamine synthetase of Sinapis alba. Z Naturforsch 43c: 194–198.

    Google Scholar 

  • Hoffmann MG, Zeiss HJ (1992) A novel and convenient route to L-homoserinlactones and L-phosphinothricin from L-aspartic acid. Tetrahedron Lett 33:2669–2672.

    Article  CAS  Google Scholar 

  • Hunter JH (1988) Desiccation of flax with glufosinate ammonium. Res Rept North Cent Weed Control Conf 45:119.

    Google Scholar 

  • IFRA/Roussel French Antilles (1987a) Basta® for weed control in banana plantations (unpublished).

    Google Scholar 

  • IFRA/Roussel French Antilles (1987b) Weed control with Basta® in bananas (unpublished).

    Google Scholar 

  • Imai S, Seto H, Sasaki T, Tsuruoka T, Ogawa H, Satoh A, Inouye S, Niida T, Otaka N (1984) Studies of the biosynthesis of bialaphos. J Antibiot 37:1505–1508.

    PubMed  CAS  Google Scholar 

  • Imai S, Tsuruoka T, Ogawa H, Sato A, Seto H, Otake N (1986) Biosynthesis of bialaphos, a herbicide produced by microorganism. Abstr Sixth Int Congr of Pestic Chem Ottawa: 2F–08.

    Google Scholar 

  • Imai S, Takane N, Yoshizawa Y, Saito T, Ogawa H, Takabe H, Sato A, Fukatsu S, Okada A, Murakami T, Hara O, Miyado S, Kumada Y, Anzai H, Nagaoka K (1987) Microbiological process for the production of L-2-amino-4-(hydroxyl-methylphosphinyl)butyric acid, a herbicide. Eur Pat Appl EP 249 188 Meiji SeikaKaisha; Chem Abstr 1988,108,130083p.

    Google Scholar 

  • Jaegers E, Boehshar M, Kleiner HJ, Erpenbach H, Bylsma F (1990) Verfahren zur Herstellung von N-Acyl-phosphinothricin-P-ester. Eur Pat Appl EP 350 630 Hoechst AG; Chem Abstr 1990,113, 41328h.

    Google Scholar 

  • Kehne H (1987) Preparation of herbicides phosphinothricin derivatives. Germ Offen DE 3 544 373 (1987) Hoechst AG; Chem Abstr 1987, 107, 78087f.

    Google Scholar 

  • Kehne H, Bauer K, Bieringer H (1987a) Preparation of phosphinothricin-containing dipeptides as herbicides. Germ Of fen DE 3 544 376 Hoechst AG; Chem Abstr 1987, 107, 97139r.

    Google Scholar 

  • Kehne H, Mildenberger H, Bauer K, Bieringer H (1987b) Phosphinothricin- containing di- and tripeptides as herbicides. Germ Of fen DE 3 544 375 Hoechst AG; Chem Abstr 1987, 107, 97140j.

    Google Scholar 

  • Kishi J, Matsumoto H, Ishizuka K (1991) Effect of glufosinate on plant seedlings growth with different nitrogen sources. Weed Res (Tokyo) 36:274–281.

    CAS  Google Scholar 

  • Koecher H, Bauer K, Donn G, Bieringer H (1981) Synergistische Kombinationen von Phosphinothricin. Eur Pat Appl 36106 Hoechst AG; Chem Abstr 1982, 96, 2163m.

    Google Scholar 

  • Koecher H (1983) Influence of the light factor on physiological effects of the herbicide phosphinothricin ammonium. Aspects Appl Biol 4:227–234.

    Google Scholar 

  • Koecher H, Loetzsch K (1985) Uptake, translocation and mode of action of the herbicide glufosinate ammonium in warm climate weed species. Proc Asian-Pac Weed Sci Soc 10:193–198.

    Google Scholar 

  • Koecher H (1989) Inhibitors of glutamine synthetase and their effects in plants. Proc Soc Chem Ind, Pestic Group Meet, Monogr 42:173–182.

    CAS  Google Scholar 

  • Kondo Y, Shomura T, Ogawa Y, Tsuruoka T, Watanabe H, Totsukawa K, Suzuki T, Moriya C, Yoshida J (1973) Isolation and physicochemical and biological characterization of SF-1293 substance. Sci Rept of Meiji Seika Kaisha 13:34–41; Chem Abstr 1974, 81, 89705b.

    Google Scholar 

  • Krieg LC, Walker MA, Senaratna T, Mc Kersie BD (1990) Effects of phosphine-thricin on growth, ammonia accumulation and glutamine synthetase activity in Alfalfa shoot tissue and cell cultures. Plant Cell Rept 9:80–83; Chem Abstr 1990, 113, 16731 lr.0

    CAS  Google Scholar 

  • Kuah TC, Langelueddeke P, Purusotman R (1989) Crop tolerance of oilpalm to long-term usage of glufosinate ammonium. Proc Asian-Pac Weed Sci Soc 12: 495–501.

    Google Scholar 

  • Kuroda Y, Okuhara M, Goto T, Okamoto M, Terano H, Kohsaka M, Aoki H, Imanaka H (1980) Studies on new phosphonic acid antibiotics. J Antibiot 33:29–35.

    PubMed  CAS  Google Scholar 

  • Lacuesta M, Gonzalez-Moro B, Gonzalez-Murua C, Aparicio-Tejo P, Munoz-Rueda A (1989) Effect of phosphinothricin on activities of glutamine synthetase and glutamate dehydrogenase in Medicago sativa. J Plant Physiol 134:304–307.

    CAS  Google Scholar 

  • Lacuesta M, Diaz A, Gonzalez-Murua C, Munoz-Rueda A (1991) Effect of glufosinate in photosynthetic electron transport. Plant Physiol 96(1) Suppl: 165.

    Google Scholar 

  • Lacuesta M, Gonzalez-Moro B, Gonzalez-Murua C, Munoz-Rueda A (1990a) Temporal study of the effect of phosphinothricin on the activity of glutamine synthetase, glutamate dehydrogenase and nitrate reductase in Medicago sativa. J Plant Physiol 136:410–414.

    CAS  Google Scholar 

  • Lacuesta M, Gonzalez-Moro B, Gonzalez-Murua C, Munoz-Rueda A (1990b) Time course effect of phosphinothricin on photosynthesis in Medicago sativa. Plant Physiol 93(1) Suppl: 936.

    Google Scholar 

  • Lacuesta M, Munoz-Rueda A, Gonzalez-Murua C, Sivak M (1992) Effect of phosphinothricin on photosynthesis and chlorophyll fluorescence emission by barley leaves illuminated under photorespiratory and nonphotorespiratory conditions. J Exp Bot 43(247): 159–165.

    Article  CAS  Google Scholar 

  • Langelueddeke P, Reuss HU, Ceconi C, Manning TH, Roettele M (1982) Glufosinate ammonium, a new nonselective contact herbicide: Results of several years experimentation in orchards and vineyards from different european countries. Med Fac Landbouw Rijksuniv Gent 47:95–104.

    CAS  Google Scholar 

  • Langelueddeke P, Purosotman R, Sellehuddin M, Kassebeer H (1983) Glufosinate ammonium a new herbicide for Imperata cylindrica and for general weed control in tropical plantation crops. Proc Asian-Pac Weed Sei Soc 9:413–423.

    Google Scholar 

  • Langelueddeke P, Buebl W (1984) Glufosinate ammonium: Neue Ergebnisse zur Unkrautbekaempfung und Vertraeglichkeit im Weinbau. Z Pflanzenkrankh Pflanzenschutz, Sonderh 10:385–394.

    Google Scholar 

  • Langelueddeke P, Takagaki T, Arceo MB (1987) Use of Basta® for weed control in vegetables. Proc Asian-Pac Weed Sei Soc 11:63–71.

    Google Scholar 

  • Langelueddeke P, Bier B, Knobloch E, Nonnen H, Winkler J (1988) Einsatz von Basta® zur Unkrautbekaempfung in Gemuese. Z Pflanzenkrankh Pflanzenschutz, Sonderheft 11:455–461.

    Google Scholar 

  • Langelueddeke P, Bier B, Buebl W, Huff HP (1989a) Crop tolerance of glufosinate ammonium in grape vines and fruit trees. Proc Eur Weed Res Soc 89:144–150.

    Google Scholar 

  • Langelueddeke P, Kocur J, Strilchuk DR (1989b) Possibilities for improving the efficacy of glufosinate ammonium. Proc Asian-Pac Weed Sei Soc 12:503–510.

    Google Scholar 

  • Langelueddeke P, Roettele M, Bier B, Kocur J (1989c) Methods of improving the efficacy of glufosinate ammonium. Proc Brit Crop Prot Conf: 1033–1038.

    Google Scholar 

  • Leader J (1988a) Glufosinate ammonium: Home and garden applications. Res Rept Expert Comm Weeds East Can 2:614–615.

    Google Scholar 

  • Leader J (1988b) Glufosinate ammonium: Home and garden applications. Res Rept Expert Comm Weeds East Can 2:656–658.

    Google Scholar 

  • Leason M, Cunliffe D, Parkin D, Lea PJ, Miflin B (1982) Inhibition of pea leaf glutamine synthetase by methioninsulfoximine. Phosphinothricin and other glutamate analogs. J Phytochem 21:855–857.

    CAS  Google Scholar 

  • Leemans J, De Block M, D’Halluin K, Botterman J, De Greef W (1987) The use of glufosinate as a selective herbicide on genetically engineered resistant tobacco plants. Proc Brit Crop Prot Conf Weeds 867–870.

    Google Scholar 

  • Lichtenstein N, Ross HE, Cohen PP (1953) Effect of a-methylglutamic acid and the enzymatic synthesis and hydrolysis of glutamine. J Biol Chem 201:117–123.

    PubMed  CAS  Google Scholar 

  • Logusch EW (1986) Facile synthesis of D, L-phosphinothricin from methyl-4-bromo-2-phthalimidobutyrate. Tetrahedron Lett 27:5935–5938.

    Article  CAS  Google Scholar 

  • Logusch E, Walker D, Mc Donald J, Franz J (1991) Inhibition of plant glutamine synthetases by substituted phosphinothricins. Plant Physiol 95:1057–1062.

    Article  PubMed  CAS  Google Scholar 

  • Maier L (1970) Synthese und Eigenschaften von Polyphosphinaten und Polyphos- phinsaeuren. Helv Chim Acta 53:1944–1947.

    Article  CAS  Google Scholar 

  • Maier L, Lea PJ (1983) Synthesis and properties of phosphinothricin derivatives. Phosphorus and Sulfur 17:1–19.

    Article  CAS  Google Scholar 

  • Makowski EJ, Faust EW (1981) Glufosinate ammonium, a new nonselective post-emergence herbicide. Proc North Cent Weed Contr Conf 36:109.

    Google Scholar 

  • Manderscheid R, Wild A (1986) Studies on the mechanism of inhibition by phosphinothricin of glutamin synthetase isolatid from Triticum aestivum. J Plant Physiol 123:135–142.

    CAS  Google Scholar 

  • Mase S (1984) Meiji Herbiace (bialaphos). A new herbicide. Jpn Pestic Inf 45:27–30, Chem Abstr 1985, 102, 162113r.

    CAS  Google Scholar 

  • Mastalerz P (1959a) Synthesis of phosphonic acids related structurally to glutamic acid. Rocz Chemii 33:985–991; Chem Abstr 1960, 54, 6602.

    CAS  Google Scholar 

  • Mastalerz P (1959b) Inhibition of glutamine synthetase by phosphonic analogs of glutamic acid. Archiwum Immunologii I Terapii Doswiadczalnej 7:201–210; Chem Abstr 1960, 54, 6843.

    CAS  Google Scholar 

  • McDonald ID, Eadie A, Mc Cann T (1987) Glufosinate ammonium for weed control in plums. Res Rept Exp Comm Weeds East Can 1:391.

    Google Scholar 

  • Miflin BJ, Lea PJ (1980) Ammonia assimilation. In: Stumpf PK, Conn EE (eds) The Biochem of Plants. Academic Press, New York, London, Vol 5, p. 171.

    Google Scholar 

  • Mildenberger H, Tammer Th (1984) Phosphinothricin. Germ Offen DE3 312 165 Hoechst AG; Chem Abstr 1985, 102, 113.735m.

    Google Scholar 

  • Minowa N, Fukatu S, Niida T, Takada M, Sato K (1983) A practical synthesis of (+)-phosphinothricin. Tetrahedron Lett 24:2391–2392.

    Article  CAS  Google Scholar 

  • Minowa N, Hirayama M, Fukatsu S (1984) Asymmetric synthesis of (+)-phosphinothricin and (+)-2-amino-4-phosphonobutyric acid. Tetrahedron Lett 25:1147–1150.

    Article  CAS  Google Scholar 

  • Minowa N, Hirayama M, Fukatsu S (1987) Asymmetric synthesis of (+)-phosphin- othricin and related compounds by the Michael addition of glycin Schiff bases to vinylcompounds. Bull Chem Soc Jpn 60:1761–1766.

    Article  CAS  Google Scholar 

  • Morocz S, Donn G, Nemeth J, Dudits D (1990) An improved system to obtain fertile regenerants via maize protoplasts isolated from a highly embryogenic suspension culture. Theor Appl Genet 80:721–726.

    Article  Google Scholar 

  • Natchev IA (1988) Enzymatic synthesis of £>-, D, L-, and L-phosphinothricin and their cyclic analogs. Bull Chem Soc Jpn 61:3699–3704.

    Article  CAS  Google Scholar 

  • Natchev IA (1989) Total synthesis and enzyme-substrate interaction of D-, D, L-> and L-phosphinothricine, bialaphos and its cyclic analogs. J Chem Soc, Perkin Trans 1:125–131.

    Article  Google Scholar 

  • Negrutiu J, Shillito R, Potrykus J, Biasini G, Sala F (1987) Hybrid genes in the analysis of transformation conditions. Plant Mol Biol 8:363–373.

    Article  CAS  Google Scholar 

  • Niida T, Inouye S, Tsuruoka T, Shomura T, Kondo Y, Ogawa Y, Watanabe H, Sekizawa Y, Watanabe T, Igarashi H (1973) Antibiotic SF-1293 from Streptomyces hygroscopicus. Germ Offen DE 2 236 599 Meiji Seika Kaisha; Chem Abstr 1973, 78, 109315t.

    Google Scholar 

  • Nir A, Raz A (1985) New herbicides for control of perennial weeds at roadsites and in drainage canals. Phytoparasitika 13:249.

    Google Scholar 

  • Oelck M, Phan C, Eckes P, Donn G, Rakow G, Keller W (1991) Field resistance of Canola transformants (Brassica napus) to Ignite® (glufosinate ammonium). GCIRC Congr Ottawa: 292–297.

    Google Scholar 

  • Ogawa Y, Tsuruoka T, Inouye S, Niida T (1973a) Chemical structure of antibiotic SF-1293. Sci Rept Meiji Seika Kaisha 13:42–48; Chem Abstr 1974, 81 37806r.

    Google Scholar 

  • Ogawa Y, Yoshida H, Inouye S, Niida T (1973b) Synthesis of a new phosphorus- containing amino acid, a component of antibiotic SF-1293. Sci Rept Meiji Seika Kaisha 13:49–53; Chem Abstr 1974, 81, 37788m.

    Google Scholar 

  • Omura S, Hinotozawa K, Imanura N, Murata M (1984a) The structure of phosa- lacine, a new herbicidal antibiotic containing phosphinothricin. J Antibiot 37: 939–940.

    PubMed  CAS  Google Scholar 

  • Omura S, Murata M, Hanaki H, Hinotozawa K, Oiwa R, Tanaka H (1984b) Phosalacine, a new herbicidal antibiotic containing phosphinothricin. Fermentation, isolation, biological activity and mechanism of action. J Antibiot 37:829–835.

    PubMed  CAS  Google Scholar 

  • O’Toole JJ, Horn J (1989) Desiccation of white beans. Res Rept Expert Comm Weeds East Can 1:332.

    Google Scholar 

  • Pace J, Me Dermott EE (1952) Methioninsulfoximine and some enzyme systems involving glutamine. Nature 169:415–416.

    Article  PubMed  CAS  Google Scholar 

  • Pamplona PP (1983) Evaluation of glufosinate ammonium, glyphosate and paraquat against weeds infesting rubber and oilpalm. Proc Asian-Pac Weed Sci Soc 9:560–569.

    Google Scholar 

  • Park BK, Hirota A, Sakai H (1977) Structure of plumbemycin A and B, antagonists of L-threonin from Streptomycesplumbeus. Agric Biol Chem 41:573–579; Chem Abstr 1977, 86, 184779r.

    Article  CAS  Google Scholar 

  • Paulus EF, Grabley S (1982) Molecular and crystal structure of L-phosphinothricin. Z Kristallogr 160:63–68.

    Article  CAS  Google Scholar 

  • Perkins GR (1990) Basta®, a new herbicide for horticulture. Proc Aust Weed Conf Meet 9: 544–547.

    Google Scholar 

  • Pfefferkorn V (1991) Neue Moeglichkeiten der Unkrautbekaempfung im Mais. 8 Maiscoll in Halle: 36–39.

    Google Scholar 

  • Purosotman R, Goetz W, Langelueddeke P (1985) Basta®, a new nonselective herbicide for general weed control in plantations. Results of long-term trials in Malaysia. Proc Asian-Pac Weed Sci Soc 10:220–226.

    Google Scholar 

  • Purusotman R, Tseu CCT, Langelueddeke P (1988) Crop tolerance and mixed weed control in cocoa with Basta®. The Planter 64(745): 171.

    Google Scholar 

  • Ratnayake S, Shaw DR (1990) Influence of harvest aid herbicides on soybean and sicklepod seed quality. Proc South Weed Sci Soc 43:30.

    Google Scholar 

  • Ratnayake S, Shaw DR (1991a) Effects of harvest aid herbicides on soybean and sicklepod (Cassia ottusifolia). Seed quality. Abstr Meet Weed Sci Soc Am 31:8.

    Google Scholar 

  • Ratnayake S, Shaw DR (1991b) Effects of harvest aid herbicides on soybean and sicklepod seed quality. Proc South Weed Sci Soc 44:346.

    Google Scholar 

  • Ridley SM, McNally SF (1985) Effects of phosphinothricin on the isoenzymes of glutamine synthetase isolated from plant species which exhibit varying degrees of susceptibility to the herbicide. Plant Science 39:31–36; Chem Abstr 1985, 103, 100292k.

    Article  CAS  Google Scholar 

  • Rioux R, Dube Z, Genderau B (1989) Potato desiccation with Basta®. Res Rept Expert Comm Weeds East Can 1:447.

    Google Scholar 

  • Roettele M, Koetter U, Fischer G (1988) Mehrjaehrige Versuchsergebnisse zur Optimierung des Produktionsverfahrens von Mais durch Direktsaat. Z Pflanzenkrankh Pflanzenschutz, Sonderh 11:203–209.

    Google Scholar 

  • Rogacheva IA, Gefter EI (1971) Transformations of bis(j3-chlorethyl)methylphos-phonite. Zh Obshch Khim 41:2634–2635; Chem Abstr 1972, 76, 127093g.

    CAS  Google Scholar 

  • Rupp W, Finke M, Bieringer H, Langelueddeke P (1977) Herbicidal composition. Germ Offen DE 2 717 440, Hoechst AG; Chem Abstr 1978, 88, 70494e.

    Google Scholar 

  • Sadler RJ, Swanton C, Sebastian D (1989) Glufosinate ammonium for desiccation of white beans. Res Rept Expert Comm Weeds East Can 1:333.

    Google Scholar 

  • Sakakura T, Huang X, Tanaka M (1991) Hydroformylation-amidocarbonylation of methylvinylphosphinate. Application to synthesis of glufosinate. Bull Chem Soc Jpn 64:1707–1709.

    Article  CAS  Google Scholar 

  • Sauer H, Wild A, Ruehle W (1987) The effect of phosphinothricin on photosynthesis II. The causes of inhibition of photosynthesis. Z Naturforsch 42c:270–278.

    Google Scholar 

  • Schoellkopf U (1983) Asymmetric synthesis of amino acids via metalated bis-lactim ethers of 2,5-diketopiperazines. Pure Appl Chem 55:1799–1806.

    Article  CAS  Google Scholar 

  • Schulz A, Taggeselle P, Tripier D, Bartsch K (1990) Stereospecific production of the herbicide phosphinothricin (glufosinate) by transamination: Isolation and characterization of a phosphinothricin-specific transaminase from Escherichia coli. Appl Environ Microbiol 56:1–6.

    PubMed  CAS  Google Scholar 

  • Schwerdtle F, Bieringer H, Finke M (1981) Glufosinate ammonium: ein neues nicht selectives Blattherbizid. Z Pflanzenkrankh Pflanzenschutz, Sonderheft 9:431–440.

    Google Scholar 

  • Seto H, Imai S, Tsuruoka T, Satoh A, Kojima M (1982) Studies of the biosynthesis of bialaphos. J Antibiot 35:1719–1721.

    PubMed  CAS  Google Scholar 

  • Seto H, Imai S, Tsuruoka T, Ogawa H, Satoh A, Sasaki T, Otake N (1983) Production of phosphinic acid derivatives, MP-103, MP-104 and MP-105 by a blocked mutant of Streptomyces hygroscopicus SF-1293 and their roles in the biosynthesis of bialaphos. Biochem Biophys Res Commun 111:1008–1014; Chem Abstr 1983, 99, 2825r.

    Article  PubMed  CAS  Google Scholar 

  • Shelby PW, Haynes RM (1988) Preplant horseweed control for no-till cotton and soybeans. Proc South Weed Sei Soc 41:294.

    Google Scholar 

  • Shimotohno K, Seto H, Otake N, Imai S, Satoh A (1986) Studies of the biosynthesis of bialaphos. J Antibiot 39:1356–1358.

    PubMed  CAS  Google Scholar 

  • Singh M, Tucker DPH (1987) Glufosinate ammonium (Ignite®): A new promising postemergence herbicide for citrus. Proc Florida State Hort Soc 100:58–61.

    Google Scholar 

  • Soroka M, Mastalerz P (1976) The synthesis of phosphonic and phosphinic analogs of aspartic acid and asparagine. Rocz Chemii 50:661–666; Chem Abstr 1977, 86, 5790t.

    CAS  Google Scholar 

  • Strauch E, Arnold W, Alijah R, Wohlleben W, Puehler A, Eckes P, Donn G, Uhlmann E, Hein F, Wengenmayer F (1988) Chemical synthesis and expression in plant cells and plants of phosphinothricin resistance gene with plant preferred codons. Eur Pat Appl EP 275 957 Hoechst AG; Chem Abstr 1989, 110, 34815z.

    Google Scholar 

  • Stuebler H (1988) Herbicidal systems for potato cultivation in West Germany under special consideration of glufosinate. Proc Weed Sei Soc Jpn, Suppl. 33:29–30.

    Google Scholar 

  • Suzuki A, Turuoka T, Mizuatam K, Inouye S (1981) New synthesis of 2-amino-4-hydroxy-4-(methylphosphinoyl)butyric acid and some analogs. Sei Rept Meiji Seika Kaisha 20:33–38; Chem Abstr 1982, 96, 103934u.

    Google Scholar 

  • Tachibana K, Watanabe T, Sekizawa Y, Takematsu T (1986) Inhibition of glutamine synthetase and quantitative changes of free amino acids in shoots of bialaphos treated Japanese barnyard millet. J Pest Science 11:27; Chem Abstr 1986, 105, 20446q.

    CAS  Google Scholar 

  • Takamatsu H, Muto H, Suzuki F (1989) Preparation of (oxopropyl)phosphinates as intermediates for herbicides. Jpn Kokai Tokky Koho JP 89 063584 Nissan Chem Ind Ltd; Chem Abstr 1989, 111, 195078x.

    Google Scholar 

  • Takematsu T, Konnai M, Tachibana K, Tsuruoka T, Inouye S, Watanabe T (1979a) Antibiotic SF-1293 as herbicide. Jpn Kokai Tokky Koho JP 79 067026 Meiji Seika Kaisha; Germ Offen DE 2 848 224, 1979; Chem Abstr 1979, 91, 85287a.

    Google Scholar 

  • Takematsu T, Konnai M, Tachibana K, Tsuruoka T, Inouye S, Watanabe T (1979b) Herbicide for controlling weeds and bushes. Germ Offen DE 2 856 260; Meiji Seika Kaisha; Chem Abstr 1979, 91, 103741a.

    Google Scholar 

  • Takigawa S, Araya S (1989) Preparation of phosphinylamino acid derivatives as intermediates for herbicides. Jpn Kokai Tokkyo Koho JP 89 249786 Nissan Chem Ind Ltd; Chem Abstr 1990, 112,158641a.

    Google Scholar 

  • Takigawa S, Araya S (1990) Preparation of aminophosphinylbutyric acid hydrochlorides as herbicides. Jpn Kokai Tokkyo Koho 90 184692 Nissan Chem Ind Ltd; Chem Abstr 1991, 114, 143708v.

    Google Scholar 

  • Takigawa S, Shinke S, Tanaka M (1990) Synthesis of glufosinate via amidocarbonylation. Chem Lett 8:1415.

    Article  Google Scholar 

  • Tanaka M, Sakakura T, Takigawa S (1989a) Preparation of organophosphinates as intermediates for herbicides. Jpn Kokai Tokkyo Koho JP 89 224382; Eur Pat Appl EP 336 558, 1989 Nissan Chem Ind Ltd; Chem Abstr 1990,112,139571m.

    Google Scholar 

  • Tanaka M, Sakakura T, Takigawa S, Araya S (1989b) Preparation of phosphinyl-2-oxobutyric acids as intermediates for herbicides. Jpn Kokai Tokkyo Koho JP 89 258692 Nissan Chem Ind Ltd; Chem Abstr 1990, 112, 179478t.

    Google Scholar 

  • Tanaka M, Sakakura T, Takigawa S, Araya S (1990) Preparation of alkyl(3-oxopropyl)phosphinic acids or their esters as intermediates for herbicidal glufosinate. Jpn Kokai Tokkyo Koho JP 90 212496 Nissan Chem Ind Ltd; Chem Abstr 1991, 114, 24194q.

    Google Scholar 

  • Then J, Bartsch K, Deger HM, Grabley S, Marquardt R (1987) Verfahren zur Herstellung von L-tertiaer-Leucin und Z-Phosphinothricin durch Transaminierung. Eur Pat Appl EP 248 357 Hoechst AG; Chem Abstr 1988, 108, 220377s.

    Google Scholar 

  • Thompson CJ, Mowa NR, Tizard R, Crameri R, Davies JE, Lauwereys M, Bottermann J (1987) Characterization of the herbicide-resistence gene BAR from Streptomyces hygroscopicus EMBO J 6: 2519–2523.

    CAS  Google Scholar 

  • Tombo GMR, Ramos D (1991) Chirality and crop protection. Angew Chem Int Ed Engl 30:1193–1215.

    Article  Google Scholar 

  • Trogisch GD, Koecher H, Ullrich WR (1989) Effects of glufosinate ammonium on anion uptake in Lemna gibba. Z Naturforsch 44c:33–38.

    Google Scholar 

  • Ullrich WR, Ullrich-Eberius CI, Koecher H (1990) Uptake of glufosinate and concomitant membrane potential changes in Lemna gibba. Pestic Biochem Physiol 37:1–11.

    Article  CAS  Google Scholar 

  • Usui K, Suwanwong S, Watanabe H, Ishizuka K (1991) Effect of benzsulfuron methyl, glyphosphate and glufosinate on amino acids and ammonium levels in carrot cells. Weed Res (Tokyo) 36:126–134.

    CAS  Google Scholar 

  • Wasielewsky C, Antczak K (1981) A new facile synthesis of phosphinothricine and 2-amino-4-phosphinobutanoic acid. Synthesis: 540–541.

    Google Scholar 

  • Weissermel K, Kleiner HJ, Finke M, Felcht UH (1981) Advances in organophosphorus chemistry based on dichloro(methyl)phosphane. Angew Chem Int Ed Engl 20:223–233.

    Article  Google Scholar 

  • Wendler Ch, Barniske M, Wild A (1990) Effect of phosphinothricin on photosynthesis and photorespiration of C3 and C4 plants. Phytosynth Res 24:55–61; Chem Abstr 1990, 112, 212420t.

    Article  CAS  Google Scholar 

  • Wendler Ch, Wild A (1990) Effect of phosphinothricin on photosynthesis and photorespiration. Z Naturforsch 45e:535–537.

    Google Scholar 

  • Wendler Ch, Putzer A, Wild A (1992) Effect of glufosinate and inhibitors of photorespiration on photosynthesis and ribulose-l,5-biphosphate carboxylase activity. J Plant Physiol 139:666–671.

    CAS  Google Scholar 

  • Wengenmayer, F (1988) Selektiver Pflanzenschlitz. Wiss Symp 125 Jahre Hoechst. Hoechst AG, Frankfurt am Main, pp 164–170.

    Google Scholar 

  • Wild A, Manderscheid R (1984) The effect of phosphinothricin on the assimilation of ammonia in plants. Z Naturforsch 39c:500–504.

    CAS  Google Scholar 

  • Wild A, Sauer H, Ruehle W (1987) The effect of phosphinothricin on photosynthesis. I. Inhibition of photosynthesis and accumulation ammonia. Z Naturforsch 42c:263–269.

    Google Scholar 

  • Wild A, Ziegler C (1989) The effect of bialaphos on ammonium-assimilation and photosynthesis. Z Naturforsch 44c:97–102.

    Google Scholar 

  • Wild A, Wendler Ch (1990) Effect of glufosinate on amino acid content, photorespiration, and photosynthesis. Pestic Science 30:422–424.

    Google Scholar 

  • Willms L (1988) Glufosinate-eine phosphorhaltige Aminosäure mit ungewöhnlichen Eigenschaften. Wiss Symp 125 Jahre Hoechst, Hoechst AG, Frankfurt am Main, pp 72–77.

    Google Scholar 

  • Willms L, Fuelling G, Keller R (1989) Enzymic resolution of racemic mixtures of phosphinothricin analogs. Eur Pat Appl EP 382 113 Hoechst AG; Chem Abstr 1991, 115, 206212x.

    Google Scholar 

  • Wise JL, Durling D (1983) Desiccation of rapeseed with glufosinate ammonium. Res Rept Expert Comm Weeds West Can 1:342.

    Google Scholar 

  • Wohlleben W, Arnold W, Broer J, Hillemann D, Strauch E, Puehler A (1988) Nucleotide sequence of phosphinothricin-N-acetyl-transferase gene from Streptomyces viridochromogenes Tue H 94 and its expression in Nicotiane tabacum. Gene 70:25–37.

    Article  PubMed  CAS  Google Scholar 

  • Worsham AD, Saunders EM (1987) Comparison of glyphosate, glufosinate and paraquat for postdirected broadspectrum weed control in corn. Proc South Weed Sei Soc 40:72.

    Google Scholar 

  • Zeiss H J (1987a) An efficient asymmetric synthesis of both enantiomers of phosphinothricin. Tetrahedron Lett 28:1255–1258.

    Article  CAS  Google Scholar 

  • Zeiss HJ (1987b) Preparation of phosphinothricin and its derivatives via hydrogénation of unsaturated precursors. Eur Pat Appl EP 238 954 Hoechst AG; Chem Abstr 1988, 108, 22285x.

    Google Scholar 

  • Zeiss HJ (1989) Method for preparation of P-containing L-a-aminobutyric acids, their esters and N-derivatives. Eur Pat Appl EP 346 658 Hoechst AG; Chem Abstr 1990, 113, 6806r.

    Google Scholar 

  • Zeiss H J (1991) Enantioselective synthesis of both enantiomers of phosphinothricin via asymmetric hydrogénation of a-acylamino acrylates. J Org Chem 56:1783–1788.

    Article  CAS  Google Scholar 

  • Zeiss H J (1992) Enantioselective synthesis of L-phosphinothricin from L-methionine and L-glutamic acid via L-vinylglycine. Tetrahedron 48(38):8263–8270.

    Article  CAS  Google Scholar 

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Hoerlein, G. (1994). Glufosinate (Phosphinothricin), A Natural Amino Acid with Unexpected Herbicidal Properties. In: Ware, G.W. (eds) Reviews of Environmental Contamination and Toxicology. Reviews of Environmental Contamination and Toxicology, vol 138. Springer, New York, NY. https://doi.org/10.1007/978-1-4612-2672-7_4

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