Benzoylprop

Last updated
Benzoylprop
Benzoylprop-ethyl.svg
Benzoylprop-ethyl
Names
Preferred IUPAC name
Ethyl N-benzoyl-N-(3,4-dichlorophenyl)-DL-alaninate
Other names
  • SD 30053
  • WL17731
  • N-Benzoyl-N-(3,4-dichlorophenyl)-DL-alanine (benzoylprop)
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • Benzoylprop-ethyl: 28825
ECHA InfoCard 100.040.753 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • Benzoylprop-ethyl:244-845-5
KEGG
PubChem CID
  • Benzoylprop-ethyl: 31068
UNII
  • Benzoylprop-ethyl:InChI=1S/C18H17Cl2NO3/c1-3-24-18(23)12(2)21(14-9-10-15(19)16(20)11-14)17(22)13-7-5-4-6-8-13/h4-12H,3H2,1-2H3
    Key: SLCGUGMPSUYJAY-UHFFFAOYSA-N
  • Benzoylprop-ethyl:CCOC(=O)C(C)N(C1=CC(=C(C=C1)Cl)Cl)C(=O)C2=CC=CC=C2
Properties
C18H17Cl2NO3
Molar mass 366.24 g·mol−1
AppearanceColourless crystalline solid [1]
20 mg/L [1]
Hazards
Lethal dose or concentration (LD, LC):
  • >1200 mg/kg (rat, oral, benzoylprop) [2]
  • 712 mg/kg (mice, oral, benzoylprop-ethyl) [1]
  • 1000 mg/kg (rat, dermal, ethyl) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Benzoylprop (or benzoylprop-ethyl) is a herbicide introduced in 1969 to control wild oats. It was considered obsolete [2] , but was reintroduced in Iran in 2017 to combat herbicide resistance. [3] It is a selective, postemergent, amide, arylalanine, arylaminopropionic acid herbicide, [4] [2] [1] [5] of the dichloroaniline propionate family. [3]

Contents

Benzoylprop-ethyl is the common chemical version, though its herbicidal activity comes after it degrades post application to benzoylprop, the acid. [4]

Data in the information box is given for benzoylprop-ethyl.

History

Benzoylprop-ethyl was introduced in 1969, [2] and to Iran in 1975. [3] In 1986, 64,000 hectares (158,000 acres) were treated with benzoylprop in the United Kingdom. [6]

The high application rate, about 1000 g/Ha active ingredient, and narrow target spectrum, of winter wild oats and wild barley made it uncompetitive against other herbicides, and in the 1990s its use ended in Iran, replaced with broad-spectrum ACCase- and ALS-inhibitor herbicides. [3] As of 2025 the Pesticide Properties Database still reports benzoylprop to be obsolete. [2]

With herbicide-resistant wild oats reported in Australia, France and Iran by 2019, and with resistant wild barley becoming common in Iran, it was re-introduced in 2017 as "Piraffix". [3]

Mechanism

Benzoylprop is a Group K, Group K3, Group 15 herbicide (Australian, Global, numeric) under the HRAC classification system of herbicide mode of action. [1] It inhibits lipid biosynthesis. [3] Other sources claim the mode of action is unknown. [7]

Benzylprop is mobile in the phloem and moves from the foliage to the stem, where it inhibits stem elongation by cellular effect. Benzylprop-ethyl is biologically inactive until degraded to benzylprop. The effect, and therefore selectivity, on plants is dependent on the rate of de-esterification (of benzoylprop-ethyl to benzoylprop) and subsequent detoxification of benzoylprop to inactive compounds. For example, the de-esterification is slow in wheat, where benzoylprop cannot build up to phytotoxic levels, and so has minimal effect, and faster in barley, and faster again in oats, where the greater amounts of benzoylprop formed stunt the crop's growth. [4]

Drought conditions reduce benzoylprop's efficacy significantly, with roughly 50% higher application rates being required. This is possibly due to reduced rate of photosynthesis, or reduced stomatal conductance, limiting herbicidal uptake. [3]

Symptoms

Affected plants have reduced elongation in leaves and stem, with the leaves a darker green and areas of chlorosis and necrosis appearing from the leaf tips, and the affected plants tended to tiller much more. [4]

Environmental behaviour

It has a moderate toxicity to fish, with an LC50 of 0.494 mg/L for freshwater fish. [1]

Formulations

It was sold as "Suffix", a Shell trademarked 20% emulsifiable concentrate, [4] , later 250 g/L, [6] and as "Endaven". [1] The 2017 reintroduction was called "Piraffix". [3]

References

  1. 1 2 3 4 5 6 7 8 Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (18 May 2016). "PPDB Benzoylprop Ethyl". Human and Ecological Risk Assessment: An International Journal. 22 (4): 1050–1064. doi:10.1080/10807039.2015.1133242 . Retrieved 21 August 2025.
  2. 1 2 3 4 5 Lewis, Kathleen A.; Tzilivakis, John; Warner, Douglas J.; Green, Andrew (18 May 2016). "PPDB Benzoylprop". Human and Ecological Risk Assessment: An International Journal. 22 (4): 1050–1064. doi:10.1080/10807039.2015.1133242 . Retrieved 21 August 2025.
  3. 1 2 3 4 5 6 7 8 Alizade, Saeid; Keshtkar, Eshagh; Mokhtasi-Bidgoli, Ali; Sasanfar, Hamidreza; Streibig, Jens C. (1 November 2020). "Effect of water deficit stress on benzoylprop-ethyl performance and physiological traits of winter wild oat (Avena sterilis subsp. ludoviciana)". Crop Protection. 137: 105292. doi:10.1016/j.cropro.2020.105292. ISSN   0261-2194.
  4. 1 2 3 4 5 Jeffcoat, Brian; Harries, W. Norton (1973). "Selectivity and mode of action of ethyl (±)-2-(N-benzoyl-3,4-dichloroamiino)propionate in the control of Arena fatua in cereals". Pesticide Science. 4 (6): 891–899. doi:10.1002/ps.2780040617.
  5. ↑ "Classification of herbicides". bcpcpesticidecompendium.org.
  6. 1 2 Matthiessen, Peter; Whale, Graham F.; Rycroft, Richard J.; Sheahan, David A. (1 September 1988). "The joint toxicity of pesticide tank-mixes to rainbow trout". Aquatic Toxicology. 13 (1): 61–75. doi:10.1016/0166-445X(88)90073-2.
  7. ↑ "бензоилпроп | PPDB". rupest.ru. Retrieved 22 August 2025.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.