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Technology of crop protection chemicals

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Surendra Bhatia

Crop protection chemicals can be classified as insecticides, herbicides, or fungicides. Key technologies for producing these chemicals include synthetic pyrethroids, neonicotinoids, organophosphorus compounds, sulfonyl ureas, triketone herbicides, FOP herbicides, imidazolinones, amide herbicides, triazole fungicides, anilide fungicides, and imidazole fungicides. Production focuses on safer intermediates and moving to more continuous processes while implementing green chemistry principles like solvent recycling.

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TECHNOLOGY OF CROP PROTECTION CHEMICALS Dr. Surendra Bhatia Sapec Agro SA
Classifications of Crop Protection Chemicals INSECTICIDES HERBICIDES FUNGICIDES Tefluthrin Rimsulfuron Fosetyl al Bifenthrin Nicosulfuron Epoxiconazole Lambda cyhalothrin Sulcotrione Cyproconazole Imidacloprid Mesotrione Difenconazole Acetamiprid Tembotrione Metalaxyl M Thiacloprid Diclofop methyl Iprodione Temephos Clodinafop propaargyl Indoxacarb Dimethenamid P s-Metolachlor Imazapic Imazethapyr
Chemistry Classifications Synthetic Pyrethroids Indanone Insecticides Organophosphorus compounds Neonicotinides Cyclohexandione Triazoles Chiral hydrogenations
SYNTHETIC PYRETHROIDS
SYNTHETIC PYRETHROIDS: KEY INTERMEDIATES LAMBDA CYHALOTHRIN 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile TEFLUTHRIN (2,3,5,6-tetrafluoro-4- methylphenyl)methanol BIFENTHRIN (2-methyl-[1,1'-biphenyl]-3-yl)methanol (E)-3-(2-chloro-3,3,3-trifluoroprop-1- en-1-yl)-2,2-dimethylcyclopropane-1- carbonyl chloride
Modifying proven technologies
NEONICOTINOIDS N-nitrosoamine destruction is the key to success
NEONICOTINOIDS: KEY INTERMEDIATES THIACLOPRID (E)-N-(thiazolidin-2-ylidene)cyanamide * ACETAMIPRID (E)-N'-cyano-N-methylacetimidamide IMIDACLOPRID
ORGANOPHOSPHOROUS COMPOUNDS Although old products , their demands are increasing if produced with High Purity
ORGANOPHOSPHOROUS COMPOUNDS: KEY INTERMEDIATES FOSETYL Al diethyl phosphonate TEMEPHOS O,O-dimethyl phosphorochloridothioate TEMEPHOS 4,4'-thiodiphenol
INDOXACARB An important insecticide from DuPont
INDOXACARB INTERMEDIATES methyl 5-chloro-1-oxo-2,3- dihydro-1H-indene-2-carboxylate methyl 5-chloro-2-hydroxy-1-oxo-2,3- dihydro-1H-indene-2-carboxylate
INDOXACARB INTERMEDIATE There are alternatives to this process. One can do carbamoylation at the end
SULFONYL UREAS
TECHNOLOGY SHIFT IN SULFONYL UREAS FROM ISOCYANATES TO CHLOROFORMATES The use of Phosgene and butylisocyanate is replaced by comparately safer intermediates like chloroformates2-Amino-4,6-dimethoxypyrimidine can be easily synthesized or procured
KEY INTERMEDIATES OF SULFONYL UREAS Nicosulfuron 2-chloronicotinic acid4,6-dimethoxypyrimidin- 2-amine Rimsulfuron 2-chloropyridin-3-amine
TRIKETONE HERBICIDES
TRIKETONE HERBICIDES: KEY INTERMEDIATES SULCOTRIONE 2-chloro-4-(methylsulfonyl)benzoyl chloride MESOTRIONE 4-(methylsulfonyl)-2-nitrobenzoyl chloride TEMBOTRIONE 2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoro ethoxy)methyl)benzoyl chloride cyclohexane-1,3-dione
FOP HERBICIDES Dicofop Me is an important compound in FOP family. The technology of the preparation of Phenoxyphenol holds the key.
FOP HERBICIDES: KEY INTERMEDIATES DICLOFOP METHYL 4-(2,4-dichlorophenoxy)phenol CLODINAFOP PROPARGYL 2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy) propanoic acid
IMIDAZOLINONE These are the herbicides from Dow
IMIDAZOLINONE: KEY INTERMEDIATES IMAZAPIC dimethyl 5-methylpyridine- 2,3-dicarboxylate COMMON INTERMEDIATE 2-amino-2,3- dimethylbutanamide IMAZETHAPYR diethyl 5-ethylpyridine-2,3- dicarboxylate
AMIDE HERBICIDES Chiral reduction is the key aspect of process development of these technologies
AMIDE HERBICIDES: KEY INTERMEDIATES DIMETHENAMID P 2,4-dimethylthiophen-3-amine S-METOLACHLOR 2-ethyl-6-methylaniline 1-methoxypropan-2-one
KEY TECHNOLOGY Preparation of Imine Chiral hydrogenation Homogeneous catalysis
TRIAZOLE FUNGICIDES
TRIAZOLE FUNGICIDES: KEY INTERMEDIATES CYPROCONAZOLE 2-(4-chlorophenyl)-2-(1- cyclopropylethyl)oxirane EPOXICONAZOLE 2-(bromomethyl)-3-(2- chlorophenyl)-2-(4- fluorophenyl)oxirane DIFENOCONAZOLE 2-(bromomethyl)-2-(2-chloro-4- (4-chlorophenoxy)phenyl)-4- methyl-1,3-dioxolane
ANILIDE FUNGICIDES It is becoming an important compound replacing metalalaxyl
ANILIDE FUNGICIDES: KEY INTERMEDIATES methyl (2,6-dimethylphenyl)alaninate 2-methoxyacetyl chloride
IMIDAZOLE FUNGICIDES Preparation of 3,5-Dichloroaniline holds the key
IMIDAZOLE FUNGICIDES: KEY INTERMEDIATES 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione 2-isocyanatopropane
Technology Focus Move from Batch Processes to Continuous/Flow Chemistry Backward Integration up to Basic Building Blocks Green Chemistry Recycle/Recovery of solvents Zero Discharge

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Technology of crop protection chemicals

  • 1. TECHNOLOGY OF CROP PROTECTION CHEMICALS Dr. Surendra Bhatia Sapec Agro SA
  • 2. Classifications of Crop Protection Chemicals INSECTICIDES HERBICIDES FUNGICIDES Tefluthrin Rimsulfuron Fosetyl al Bifenthrin Nicosulfuron Epoxiconazole Lambda cyhalothrin Sulcotrione Cyproconazole Imidacloprid Mesotrione Difenconazole Acetamiprid Tembotrione Metalaxyl M Thiacloprid Diclofop methyl Iprodione Temephos Clodinafop propaargyl Indoxacarb Dimethenamid P s-Metolachlor Imazapic Imazethapyr
  • 3. Chemistry Classifications Synthetic Pyrethroids Indanone Insecticides Organophosphorus compounds Neonicotinides Cyclohexandione Triazoles Chiral hydrogenations
  • 5. SYNTHETIC PYRETHROIDS: KEY INTERMEDIATES LAMBDA CYHALOTHRIN 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile TEFLUTHRIN (2,3,5,6-tetrafluoro-4- methylphenyl)methanol BIFENTHRIN (2-methyl-[1,1'-biphenyl]-3-yl)methanol (E)-3-(2-chloro-3,3,3-trifluoroprop-1- en-1-yl)-2,2-dimethylcyclopropane-1- carbonyl chloride
  • 8. NEONICOTINOIDS: KEY INTERMEDIATES THIACLOPRID (E)-N-(thiazolidin-2-ylidene)cyanamide * ACETAMIPRID (E)-N'-cyano-N-methylacetimidamide IMIDACLOPRID
  • 9. ORGANOPHOSPHOROUS COMPOUNDS Although old products , their demands are increasing if produced with High Purity
  • 10. ORGANOPHOSPHOROUS COMPOUNDS: KEY INTERMEDIATES FOSETYL Al diethyl phosphonate TEMEPHOS O,O-dimethyl phosphorochloridothioate TEMEPHOS 4,4'-thiodiphenol
  • 11. INDOXACARB An important insecticide from DuPont
  • 12. INDOXACARB INTERMEDIATES methyl 5-chloro-1-oxo-2,3- dihydro-1H-indene-2-carboxylate methyl 5-chloro-2-hydroxy-1-oxo-2,3- dihydro-1H-indene-2-carboxylate
  • 13. INDOXACARB INTERMEDIATE There are alternatives to this process. One can do carbamoylation at the end
  • 15. TECHNOLOGY SHIFT IN SULFONYL UREAS FROM ISOCYANATES TO CHLOROFORMATES The use of Phosgene and butylisocyanate is replaced by comparately safer intermediates like chloroformates2-Amino-4,6-dimethoxypyrimidine can be easily synthesized or procured
  • 16. KEY INTERMEDIATES OF SULFONYL UREAS Nicosulfuron 2-chloronicotinic acid4,6-dimethoxypyrimidin- 2-amine Rimsulfuron 2-chloropyridin-3-amine
  • 18. TRIKETONE HERBICIDES: KEY INTERMEDIATES SULCOTRIONE 2-chloro-4-(methylsulfonyl)benzoyl chloride MESOTRIONE 4-(methylsulfonyl)-2-nitrobenzoyl chloride TEMBOTRIONE 2-chloro-4-(methylsulfonyl)-3-((2,2,2-trifluoro ethoxy)methyl)benzoyl chloride cyclohexane-1,3-dione
  • 19. FOP HERBICIDES Dicofop Me is an important compound in FOP family. The technology of the preparation of Phenoxyphenol holds the key.
  • 20. FOP HERBICIDES: KEY INTERMEDIATES DICLOFOP METHYL 4-(2,4-dichlorophenoxy)phenol CLODINAFOP PROPARGYL 2-(4-((5-chloro-3-fluoropyridin-2-yl)oxy)phenoxy) propanoic acid
  • 21. IMIDAZOLINONE These are the herbicides from Dow
  • 22. IMIDAZOLINONE: KEY INTERMEDIATES IMAZAPIC dimethyl 5-methylpyridine- 2,3-dicarboxylate COMMON INTERMEDIATE 2-amino-2,3- dimethylbutanamide IMAZETHAPYR diethyl 5-ethylpyridine-2,3- dicarboxylate
  • 23. AMIDE HERBICIDES Chiral reduction is the key aspect of process development of these technologies
  • 24. AMIDE HERBICIDES: KEY INTERMEDIATES DIMETHENAMID P 2,4-dimethylthiophen-3-amine S-METOLACHLOR 2-ethyl-6-methylaniline 1-methoxypropan-2-one
  • 25. KEY TECHNOLOGY Preparation of Imine Chiral hydrogenation Homogeneous catalysis
  • 27. TRIAZOLE FUNGICIDES: KEY INTERMEDIATES CYPROCONAZOLE 2-(4-chlorophenyl)-2-(1- cyclopropylethyl)oxirane EPOXICONAZOLE 2-(bromomethyl)-3-(2- chlorophenyl)-2-(4- fluorophenyl)oxirane DIFENOCONAZOLE 2-(bromomethyl)-2-(2-chloro-4- (4-chlorophenoxy)phenyl)-4- methyl-1,3-dioxolane
  • 28. ANILIDE FUNGICIDES It is becoming an important compound replacing metalalaxyl
  • 29. ANILIDE FUNGICIDES: KEY INTERMEDIATES methyl (2,6-dimethylphenyl)alaninate 2-methoxyacetyl chloride
  • 30. IMIDAZOLE FUNGICIDES Preparation of 3,5-Dichloroaniline holds the key
  • 31. IMIDAZOLE FUNGICIDES: KEY INTERMEDIATES 3-(3,5-dichlorophenyl)imidazolidine-2,4-dione 2-isocyanatopropane
  • 32. Technology Focus Move from Batch Processes to Continuous/Flow Chemistry Backward Integration up to Basic Building Blocks Green Chemistry Recycle/Recovery of solvents Zero Discharge