Chemistry

Dr. Mikhail Bobylev

Professor

Office: 329 CMSC
Email: mikhail.bobylev@minotstateu.edu
Phone: 858-3066

Chemistry 110 - Survey of Chemistry
Chemistry 115 - Introductory Chemistry
Chemistry 121 - General Chemistry I
Chemistry 122 - General Chemistry II
Chemistry 341 - Organic Chemistry I
Chemistry 342 - Organic Chemistry II
Chemistry 440 - Organic Spectroscopy

Education:
Ph.D., 1985. Institute of Plant Protection Chemicals, Moscow, Russia
M.S., 1973 Moscow State University, Moscow, Russia

Academic Experience:
2002- Assistant Professor, Minot State University, Minot, ND
2001 2002 Visiting Assistant Professor, Agnes Scott College, Atlanta, GA
1997 2002 Assistant Research Professor, Mercer University, Atlanta, GA
1993 1997 Visiting Research Professor, Montana State University, Bozeman, MT

Industrial Experience:
1985 1993 Senior Scientist/Group Leader, Institute of Plant Protection Chemicals (IPPC), Moscow, Russia
1973 1985 Research Scientist, Institute of Plant Protection Chemicals, Moscow, Russia

Information and Publishing Experience/Concurrent Employment:
1985-1993 Scientific Editor, Institute of Scientific and Research Information, Russian Chemical Abstracts Magazine (RZh Khimiya), Moscow, Russia

1975-1985 Abstractor, Institute of Scientific and Research Information, Russian Chemical Abstracts Magazine (RZh Khimiya), Moscow, Russia

Teaching Experience:

• General Chemistry & Lab, Organic Chemistry & Lab, Organic Spectroscopy & Lab, Biochemistry & Lab, Medicinal Chemistry & Lab (Minot State University & Agnes Scott)
• Served as a lecturer in a graduate class in plant biochemistry (Montana State University).
• Supervised graduate student research in synthetic organic chemistry (Institute of Plant Protection Chemicals). " Mentored and guided junior researchers in organic synthesis and chemistry of biologically active compounds (Institute of Plant Protection Chemicals).
• Made numerous oral presentations at International and National scientific meetings.
• Served as an interpreter and translator for Russian artists and dignitaries (Montana).

Research Interests:

• Rational drug design of fungicides for medicine, veterinary, and agriculture.
• Structure-activity relationships of small peptides and peptidomimetics as plant growth regulators and herbicides.
• Design and synthesis of environmentally friendly agrochemicals and safe pharmaceuticals based on natural templates.

Major Accomplishments:
Discovered and mapped plant growth regulation activity of maculosin analogs (Mercer).

 

Designed and synthesized new type herbicides based on maculosin template (MSU)

Discovered broad spectrum phytotoxicity of phenylalanine derivatives (MSU)

Designed, developed, and registered Ascostatin, a novel fungicide for veterinary (IPPC)

Developed radically new one-step process for obtaining Ascostatin and analogs (IPPC)

Designed and synthesized a totally novel group of formamide fungicides (IPPC).

Designed and synthesized chloral derivatives as potential broad spectrum fungicides (IPPC).

Developed selective synthesis of halogenated aromatic aldehydes and dialdehydes (IPPC). " R&D of Azovit, a trizole fungicide registered for application in agriculture (IPPC).

Organized and led collaborative study of medicinal applications of Ascostatin (IPPC).

International collaboration with KEMIRA AGRO OY, Espoo, Finland (IPPC).

International collaboration with Long Ashton Research Station, UK (IPPC).

Managed external R&D projects (IPPC).

Professional Activity:
From 1987 to 1993 served two terms on Council of Employees (equivalent of a Board of Directors), Institute of Plant Protection Chemicals, Moscow, Russia, elected by all employees at state-owned enterprises that had an equal right with the owner to hire the Director of the Institute. In 1992 was elected as a sole Council Representative empowered to sign the Institute's contract with its Director.

Professional Societies:
American Chemical Society
Division of Agrochemicals, American Chemical Society
Division of Chemical Education, American Chemical Society
Division of Medicinal Chemistry, American Chemical Society
Division of Organic Chemistry, American Chemical Society
American Association for the Advancement of Science
Plant Growth Regulation Society of America
Russian Chemical Society
Russian Society of Inventors

International Activity and Community Service:
1994-to present provided Montana Arts Foundation international contacts with artists in Russia, historical information and perspective on Russian art, and orientation to Russian artists participating in a cultural exchange in the State of Montana. Served as interpreter for the Montana Arts Foundation during a meeting of Montana's Governor, a representative of USIA, and the President of the Russian Academy of Arts. Translated all communication with Russian Academy of Arts that resulted in Montana's first truly international visual art exhibition in October, 1998, in Billings, Montana. Translated Russian essay for exhibition catalog.

1994-97 translated all correspondence between composer Patty Carlson, Red Lodge, Montana, and Andrei Petrov, Director of the Kremlin Palace Theater, Moscow, regarding the Bolshoi Ballet's interest in and future performance of Ms. Carlson's new ballet score.

Grants:
1992 Received grant form German Phytomedicinal Society to visit 10th International Symposium on Systemic Fungicides and Antifungal Compounds, Reinhardsbrunn, Germany,

May 3-9, 1992. 1992 Received grant from Agricultural and Food Research Council (UK) to
visit Long Ashton Research Station, Bristol, UK.

1993 Received grant from the British Council to visit Long Ashton Research Station, Rothamsted Experimental Station, and Jealott's Hill Research Station (ICI Agrochemicals).

1993 Received grant from Montana Noxious Weeds Trust Fund to study analogs of maculosin as potential bioherbicides.

1996 Received grant from Beim Foundation to conclude the study of maculosin analogs.

1998 Received grant from International Ag Labs to study plant growth regulating substances produced by microorganisms.

1998 Received grant from the USDA to work on isolation of sprout regulatory metabolites from bacterial antagonists of potato dry rot.

1999 Received grant from International Ag Labs to study fungicidal substances produced by microorganisms.

2001 Received grant from the USDA to work on isolation of antifungal metabolites from bacterial antagonists of potato dry rot.

2002 Research Scholar Program grant from Agnes Scott College to study structure-activity relationships of novel anti-fungal drugs. BRIN Phase II Grant (2002)

College Research Grant (College of Arts and Sciences, Minot State University, 2002)

Faculty Small Research Grant (2002, Minot State University)

2003 EPSCoR Flare Grant (2003)

Recent Publications:
Bobylev M. M., Bobyleva L. I., Cutler H. G., Cutler S. J., and Strobel G. A. Effects of Synthetic Congeners of the Natural Product Phytotoxins Maculosins 1 and 2 on Growth of Wheat Coleoptile (Triticum aestivum L. cv. Wakeland). In: Spencer, Neal R. (ed.) 2000. Proceedings
of the X International Symposium on Biological Control of Weeds. Bozeman, Montana, USA, 4-14 July 1999, United States Department of Agriculture, Agricultural Research Service, Sidney, MT, and Montana State University - Bozeman, Bozeman, MT, 1030 p., pp. 209-214.

Bobylev M. M., Bobyleva L. I., Cutler H. G., Cutler S. J., and Strobel G. A. Growth Regulating Activity of Maculosin Analogs in the Etiolated Wheat Coleoptile Bioassay (Triticum aestivum L. cv. Wakeland). PGRSA Quarterly 1999, 27(4), 105-118.

Bobylev, M. M., Loeffler, R. S. T. Investigation of the Activity and Mode of Action of Compounds Related to Chloralformamide Fungicides. In: Modern Fungicides and Antifungal Compounds II. Intercept, Andover, UK, pp. 85-92, 1999. (Book Chapter).

Bobylev, M. M., Bobyleva, L. I., Strobel, G. A. Natural products containing phenylalanine as potential bioherbicides. In: Biologically Active Natural Products: Agrochemicals and Pharmaceuticals. CRC Press, Boca Raton, pp. 169-174, 1999. (Book Chapter).

Popkov, S. V.; Kovalenko, L. V.; Bobylev, M. M.; Molchanov, O. Yu.; Krimer, M. Z.; Tashchi, V. P.; Putsykin, Yu. G. The Synthesis and Fungicidal Activity of 2-substituted
1-azol-1-ylmethyl-6-arylidenecyclohexanols. Pestic. Sci. 1997, 49(2),
125-9.

Bobylev, M. M.; Bobyleva, L. I.; Strobel, G.A. Synthesis and Bioactivity of Analogs of Maculosin, a Host Specific Phytotoxin Produced by Alternaria alternata on Spotted Knapweed (Centaurea maculosa). J. Ag. Food Chem. 1996, 44(12), 3960-3964.

Kovalenko, L. V.; Popkov, S. V.; Bobylev, M. M.; Molchanov, O. Yu.; Krimer, M. Z.; Tashchi, V. P.; Putsykin, Yu. G. Synthesis and Fungicidal Activity of 2-substituted 1-azolylmethyl-6-benzylidenecyclohexanols. Agrokhimiya 1994, (7-8), 76-81 (Russian) ); CA 121: 198421w.

Selected Patents:
1. N-METHYL-N-(2,2,2-TRICHLORO-1-OXYETHYL)FORMAMIDE POSSESSING
FUNGICIDAL ACTIVITY AND THE METHOD FOR ITS OBTAINING. Bobylev et al.
U.S.S.R. SU 610,370, 14 Feb 1978, Appl. 2,388,207, 01 Aug 1976

CARBAMATES OF CHLORALKETONES POSSESSING FUNGICIDAL AND BACTERICIDAL ACTIVITY. Bobylev, M.M.; Zakirov, A.V.; Andreeva N.G.; Milshtein, I.M.;
Shvetsova-Shilovskaya, K.D.; Kondratiev, Yu.A.; Andreeva, E.I.; Pronchenko, T.S.; Smirnova, K.F.; Usmanov, M.T.; Sanin, M.A.; Golyshin, N.M. U.S.S.R. SU 707, 174, 08 Sep 1979, Appl. 2,617,588, 22 May 1978

CARBAMATES OF N-METHYLOLTRICHLOROACETAMIDE POSSESSING FUNGICIDAL
ACTIVITY. Bobylev, M.M.; Milshtein, I.M.; Shvetsova-Shilovskaya, K.D.; Andreeva, E.I.; Pronchenko, T.S.; Sanin, M.A.; Usmanov, M.T.; Petrova, L.P. U.S.S.R. SU 711, 768, 28 Sep 1979, Appl. 2,476,001, 18 Apr. 1977

1,1,1-TRICHLORO-2-HYDROXY-4-(4-NITROPHENYL)-4-BUTANONE AS A
SEMIPRODUCT FOR SYNTHESIS OF 1,1,1-TRICHLORO-4-(4-NITROPHENYL)-2-BUTEN-4-ONE AND 1,1,1-TRICHLORO-4-(4-NITROPHENYL)-2-BUTEN-4-ONE AS A FUNGICIDE. Bobylev, M.M.; Putsykin Yu.G.; Velesevich, S.M.; Andreeva, E.I.; Sanin, M. A.;Zaikin, B.A.; Ponomareva, E.E. U.S.S.R. SU 1,086,720, 15 Dec 1983, Appl. 3,464,593, 02 Jul 1982

DIOXANE DERIVATIVE FUNGICIDE. Bobylev, M.M.; Putsykin, Yu.G.; Velesevich, S.M., Andreeva, E.I.; Pronchenko, T.S.; Akhmatova, N.I. U.S.S.R. SU 1,099,426 (Cl. A01N43/32), 15 Dec, 1992, Appl. 3,507,102, 01 Nov 1982; CA 119: 65649p.

FUNGICIDE. Bobylev, M.M.; Velesevich, S.M.; Putsykin Yu.G.; Andreeva,
E.I.; Pronchenko, T.S.; Usmanov, M.T.; Abelentsev, V.I.; Sanin, M.A.; Akhmatova, N.I.; et al. U.S.S.R. SU 1,197,165 (Cl. A01N33/18), 28 Feb 1993, Appl 3,768,547, 12 Jul 1984; CA 119: 2435888c.

4,4,4-TRICHLORO-3-OXY-4-NITROBUTYROPHENONOXIME POSSESSING FUNGICIDE
ACTIVITY. Bobylev, M.M.; Putsykin, Yu.G.; Sanin, M.A. U.S.S.R. SU 1,094,273 (Cl. C07C251/48) 28 Feb 1993, Appl. 3,524,069, 28 Oct 1982; CA 119: 266363q.

4-AMINO-1-[3,3-DIMETHYL-2-OXO-1-(4-CHLOROPHENOXY)-BUT-1-YL]-1,2,4-TRIAZOLIUM
CHLORIDE AS AN INTERMEDIATE PRODUCT IN THE SYNTHESIS OF 3,3-DIMETHYL-1-(1,2,4-TRIAZOL-1-YL)-1-(4-CHLOROPHENOXY)BUTAN-2-ONE. Bobylev M. M. et al. U.S.S.R. SU 1,669,152, 08 Apr 1991, Appl. 4,340,010, 09 Dec 1987

1-(2,4-DICHLOROPHENYL)-4,4-DIMETHYLPENT-1-EN-3-YL-ISOCYANIDE SHOWING
FUNGICIDAL ACTIVITY. Bobylev, M. M.; Chekhlov, A. P.; Eremina, V. A.; Velesevich, S. M.; Krivojchenko, I. N.; Putsykin, Yu. G.; Polyakov, A. I.; Abelentsev, V. I.; Sanin, M. A.; et al. U.S.S.R. SU 1,833,401 (Cl. C07C291/10), 07 Aug 1993, Appl. 4,898,630, 03 Jan 1991; CA 123: 251120s.

1-(2,4-DICHLOROPHENYL)-FORMAMIDOPENTANES SHOWING FUNGICIDAL ACTIVITY. Bobylev, M. M.; Eremina, V. A.; Velesevich, S. M.; Putsykin, Yu. G.; Sanin, M. A.; Grechikhina, T. V. U.S.S.R. SU 1,833,369 (Cl. C07C233/03), 07 Aug 1993, Appl. 4,899,136, 03 Jan 1991; CA 123: 310212y.

2-DERIVATIVES OF 1,1,1-TRICHLORO-4-(2,4-DICHLOROPHENYL)-4-BUTANONE SHOWING ANTIMICROBIAL ACTIVITY, AND 111-TRICHLORO-2-HYDROXY-4-(2,4-DICHLOROPHENYL)-4-BUTANONE AS A SEMIPRODUCT FOR SYNTHESIS OF 2-DERIVATIVES OF 111-TRICHLORO-4-(2,4-DICHLOROPHENYL)-4-BUTANONE. Bobylev, M. M.; Velesevich, S. M.; Putsykin, Yu. G.; Vorobev, A. A.; Silin, V. A.; Mironov, A. Yu.; Lobashevskij, A. L.; Leshchenko, V. M. U.S.S.R. SU 1,734,343 (Cl. C07C49/697), 30 Mar 1994, Appl. 4,686,243, 03 May 1989; CA 123: 285519u.

SUBSTITUTED 1-(1H-1,2,4-TRIAZOL-1-YLMETHYL)CYCLOHEXANOLS SHOWING
FUNGICIDAL ACTIVITY AND SUBSTITUTED OXYRANES AS INTERMEDIATES FOR THEIR PREPARATION. Suokas, E.; Putsykin, Yu. G.; Bobylev, M. M.; Tashchi, V. P.; Abelentsev, V. I.; Sanin, M. A.; Molchanov, O. Yu.; Kovalenko, L. V.; Popkov, S. V. U.S.S.R. SU 1,838,304 (Cl. C07C249/12), 30 Aug 1993, Appl. 4,927,588, 18 April 1991; CA 123: 286047u.

2,2-DIMETHYLPROPANE ISONITRILE DERIVATIVES POSSESSING SYNERGISTIC ACTIVITY TOWARD INSECTICIDES, AND 2,2-DIMETHYLPROPANE FORMAMIDE DERIVATIVES AS THEIR INTERMEDIATES. Chekhlov, A. P.; Polyakov, A. I.;
Pereguda, T. A.; Promonenkov, V. K.; Bobylev, M. M.; Agashkova, T. A.; Krivojchenko, I. N. U.S.S.R. SU 1,836,363 (Cl. C07C333/28), 23 Aug 1993, Appl. 4,898,684, 03 Jan 1991; CA 124: 55786v.

FUNGICIDAL AZOLYLMETHYLCYCLOHEXANOLS. Suokas, E.; Putsykin, Yu. G.; Bobylev, M. M.; Tashchi, V. P.; Abelentsev, V. I.; Sanin, M. A.; Molchanov, O. Yu.; Kovalenko, L. V.; Popkov, S. V. Finn FI 95,571 (Cl. C07D), 30 Nov 1995, Appl. 90/2,011, 23 April 1990; CA 124: 289552t.

Presentations:
North Dakota Academy of Science, North Dakota State University, Fargo, North Dakota, April 29, 2004

Mikhail M. Bobylev, Robin M. Gonzalez. Green chemistry: One pot synthesis of novel formamide fungicides.

227th ACS National Meeting, Anaheim, California, March 28-April 1, 2004.

Mikhail M. Bobylev, Robin M. Gonzalez. Green chemistry: One pot synthesis of novel formamide fungicides.

Mikhail M. Bobylev, Christopher L. Aaron, Marisa A. Upton. Optimization of Leuckart Reaction for the Synthesis of Novel Formamide Fungicides.

Mikhail M. Bobylev. Extraction of caffeine from tea: Optimization of the old classic procedure as a research project for undergraduate chemistry lab.

Mikhail M. Bobylev, Cory P. Mattern. Extraction of caffeine from tea: Optimization of the procedure.

2003 ND/SD EPSCoR Joint Conference, North Dakota State University, Fargo, North Dakota, September 5, 2003

Mikhail M. Bobylev*, Christopher L. Aaron, Marisa A. Upton. Optimization of Leuckart Reaction for the Synthesis of Novel Formamide Fungicides

North Dakota Academy of Science, Minot State University, Minot, North Dakota, April 28, 2003

Mikhail M. Bobylev. Establishing Drug Discovery Research Program at Minot State University: Organic Chemistry and Biochemistry Input in Developing North Dakota Biomedical Research Infrastructure Network

27th Annual Meeting of the Plant Growth Regulation Society of America held jointly with the Japanese Society for the Chemical Regulation of Plants Kailua Kona, Hawaii, July 30 - August 3, 2000

L. P. Meagher, M. M. Bobylev, P. J. Slininger, D. A. Schisler, and H. G. Cutler Biological Control of Sprouting in Potato Tubers by Dry Rot Antagonistic Bacteria.

219th ACS National Meeting, San Francisco, California, March 26 30, 2000.

Bobylev M. M., Bobyleva L. I., Cutler H. G., Cutler S. J., and Strobel G. A. Synthetic congeners of the natural product phytotoxin maculosin 2 possessing a modified diketopiperazine moiety, and their effects on the growth of wheat coleoptiles (Triticum aestivum L. cv. Wakeland).

218th ACS National Meeting, New Orleans, Louisiana, August 22 26, 1999.

Bobylev M. M., Bobyleva L. I., Cutler H. G., Cutler S. J., and Strobel G. A. Effects Of Individual Stereoisomers Of The Natural Product Phytotoxin Maculosin 2 And Its Synthetic Congeners On Growth Of Wheat Coleoptile (Triticum aestivum L. cv. Wakeland).

X International Symposium on Biological Control of Weeds, Bozeman, Montana, July 4 July 9, 1999.

Bobylev M. M., Bobyleva L. I., Cutler H. G., Cutler S. J., and Strobel G. A. Effects of Synthetic Congeners of the Natural Product Phytotoxins Maculosins 1 and 2 on Growth of Wheat Coleoptile (Triticum aestivum L. cv. Wakeland).

16th International Conference on Plant Growth Substances, Makuhari Messe, Chiba, JAPAN, August 13 - 17, 1998. Invited Speaker.

Bobylev, M. M.; Bobyleva, L. I.; Strobel, G. A. Development of Natural Products As Potential Bioherbicides.

12th International Reinhardsbrunn Symposium on Modern Fungicides and Antifungal Compounds, Reinhardsbrunn, GERMANY, May 24th - May 29th 1998. Bobylev, M., Loeffler, T. Investigation of the Activity and Mode of Action of Compounds Related to Chloralformamide Fungicides

214th ACS National Meeting, Las Vegas, September 7 11, 1997.

Bobylev, M. M.; Bobyleva, L. I.; Strobel, G. A. Natural products containing phenylalanine as potential bioherbicides.

210th ACS National Meeting, Chicago, August 20-24, 1995.

Bobylev, M., Loeffler, T. Investigation of the Activity and Mode of Action of Compounds Related to Chloralformamide Fungicides

Bobylev, M. M.; Strobel, G. A.; Bobyleva, L. I. Synthesis and bioactivity of analogs of maculosin, the first truly host specific phytotoxin produced by Alternaria alternata on spotted knapweed
(Centaurea maculosa).

10th International Symposium on Systemic Fungicides and Antifungal Compounds, Reinhardsbrunn, GERMANY, May 3-9, 1992; published in German Phytomedical Society Series 1993, 4:

pp 329-333 Bobylev, M.; Eremina, V.; Molchanov, O.; Velesevich, S.; Margolin, L. Triforine: what plays the role of the triazole?

pp 335-337 Bobylev, M.; Molchanov, O.; Fedorov, E.; Velesevich, S. Azovit: new properties of an old fungicide.