Flamprop

Last updated
Flamprop
Flamprop.svg
Names
Preferred IUPAC name
2-(N-Benzoyl-3-chloro-4-fluoroanilino)propanoic acid
Other names
  • N-Benzoyl-N-(3-chloro-4-fluorophenyl)-DL-alanine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 840-987-2
KEGG
PubChem CID
UNII
  • InChI=1S/C16H13ClFNO3/c1-10(16(21)22)19(12-7-8-14(18)13(17)9-12)15(20)11-5-3-2-4-6-11/h2-10H,1H3,(H,21,22)
    Key: YQVMVCCFZCMYQB-UHFFFAOYSA-N
  • CC(C(=O)O)N(C1=CC(=C(C=C1)F)Cl)C(=O)C2=CC=CC=C2
Properties
C16H13ClFNO3
Molar mass 321.73 g·mol−1
AppearanceWhite crystals [1]
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Flamprop is a selective post-emergent herbicide, used in Australia on wheat and triticale. [2] It is an arylalanine. [1] Flamprop was introduced circa 1974, with some variants coming a few years later. [1] Flamprop comes in several chemical variants, including flamprop, flamprop-methyl, flamprop-isopropyl, flamprop-M, flamprop-M-methyl, and flamprop-M-isopropyl. [3] The information in the right hand side box is accurate for basic flamprop.

Contents

Initial research focussed on wild oats in cereal crops in the 60s and 70s, with several chemical variants studied. [4] Flamprop was introduced in the UK circa 1984. [5]

In Australia, flamprop is sold as a 90 g/L concentrate, and applied at 112-225 g/Ha. [2]

Under moderately basic conditions, the varieties of flamprop are hydrolysed to their base acids and alcohols. Under more basic conditions, there can be cleavage of the amide bond, giving benzoic acid and the corresponding amino acid. [4]

By 2000, resistant wild oats (Avena fatua) were found in Canada. The wild oat was estimated to cost Canada $300 million annually, and at about the same time resistant examples were found to ACCase inhibitors and triallate, and difenzoquat. [6]

Mechanism

All flamprop variants are HRAC Group Z or 0, as the mode of action is classed as unknown. It is suspected to be the prevention of cell elongation [1] at the meristematic regions. Selectivity is possible because of differential metabolism, especially at the de-esterification, which is quicker in wild oats than in wheat and barley. [5]

Formulation

Flamprop formulations have long needed an oil based adjuvant for good performance. Originally, this was 30 to 36% napthenic and 9 to 25% aromatic compounds in an emulsifiable concentrate. However, even more adjuvant was found necessary than could be provided in concentrated formulations, so farmers were advised to add extra oil (sometimes sold as "Swirl", though a 1994 study suggests the effect was small). The most effective adjuvant was 'Dobanol 25-7'. Flamprop's recommended application rate was 600 grams active ingredient per hectare. Nonylphenol ethoxylates and alylamine ethodxylates were tested, and were worse or approximately equal to Swirl. The best adjuvants were 'Genamin' C050 and 'Dobanol' 25-7. [5]

'Commando' was a 200 g/L formulation of flamprop-M-isopropyl. [5]

Variants

Flamprop Variants [7]
VariantCASFormulaMolar massSolubility
Flamprop58667-63-3C16H13ClFNO3321.73 g/mol
Flamprop-methyl52756-25-9C17H15ClFNO3335.8 g/mol35 mg/L [4]
Flamprop-isopropyl52756-22-6C19H19ClFNO3363.8 g/mol18 mg/L [4]
Flamprop-M-methyl63729-98-6C17H15ClFNO3335.8 g/mol
Flamprop-M-isopropyl63782-90-1C19H19ClFNO3363.8 g/mol
Flamprop-M90134-59-1C16H13ClFNO3321.73 g/mol
Flamprop-ethyl34029-27-1C18H17ClFNO3349.8 g/mol13 mg/L [4]
Benzoylprop-ethyl34029-27-1C18H17ClFNO3349.8 g/mol20 mg/L [4]
Flamprop's variants Flamprop variants.png
Flamprop's variants

Benzoylprop-ethyl is a closely related herbicide studied in the same development program, first introduced in 1969, though it is now considered obsolete. [4]

References

  1. 1 2 3 4 Flamprop in the Pesticide Properties Database, accessed 6 March 2025
  2. 1 2 "FLAMPROP 90 LABEL" (PDF). Titan AG. Retrieved 6 March 2025.
  3. ↑ "PPDB A to Z Index". sitem.herts.ac.uk.
  4. 1 2 3 4 5 6 7 Grayson, B. Terence; Stokes, Sylvia (December 1978). "Hydrolysis of the wild oat herbicides flamprop‐methyl, flamprop‐ethyl, flamprop‐isopropyl and benzoylprop‐ethyl". Pesticide Science. 9 (6): 595–602. doi:10.1002/ps.2780090616.
  5. 1 2 3 4 Grayson, B. Terence; Boyd, Sarah L.; Walter, David (February 1995). "Reinvestigating adjuvants for the wild oat herbicide, flamprop‐M‐isopropyl. I: Glasshouse trials". Pesticide Science. 43 (2): 147–155. doi:10.1002/ps.2780430208.
  6. ↑ Friesen, Lyle F.; Jones, Tammy L.; Van Acker, Rene C.; Morrison, Ian N. (2000). "Identification of Avena fatua Populations Resistant to Imazamethabenz, Flamprop, and Fenoxaprop-P". Weed Science. 48 (5): 532–540. ISSN   0043-1745.
  7. 1 2 "PubChem". pubchem.ncbi.nlm.nih.gov.
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