Benzadox

Benzadox[1]
Names
Preferred IUPAC name
(benzamidooxy)acetic acid
Other names
  • Topcide (brand name)
  • S6175[2]
  • 2-[(benzoylamino)oxy]acetic acid
  • benzamidooxyacetic acid[3]
  • benzamido-oxyacetic acid[2]
  • o-Benzamidoglycolic acid[4]
  • ((Benzoylamino)oxy)acetic acid[4]
  • S-7173 or S-7,173[4]
  • Topicide (brand name)[4]
  • NSC 75601[4]
  • N-benzoyl-O-(carboxymethyl)-hydroxylamine[4]
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.023.685
EC Number
  • 226-053-1
UNII
  • InChI=1S/C9H9NO4/c11-8(12)6-14-10-9(13)7-4-2-1-3-5-7/h1-5H,6H2,(H,10,13)(H,11,12)
    Key: WDRGQGLIUAMOOC-UHFFFAOYSA-N
  • C1=CC=C(C=C1)C(=O)NOCC(=O)O
Properties
C9H9NO4
Molar mass 195.174 g·mol−1
Appearance Off-white solid[5]
Odor Odourless[5]
Melting point 140 °C (284 °F; 413 K) [5]
Hazards
GHS labelling:[5]
H302
P264, P270, P301+P317, P330, P501
Lethal dose or concentration (LD, LC):
>2500 mg/kg (rat, benzadox-ammonium)[2]
Related compounds
Related compounds
 Benzadox-ammonium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Benzadox is an amide herbicide, first discovered in 1966 to control kochia on sugarbeet crops.[6] Commercial benzadox products are often sold as benzadox-ammonium, benzadox's ammonium salt.[1] See that page for its chemical properties. Benzadox is not known to be in current use,[2] and most research about it seems to be from the 1960s and 1970s.

Benzadox appears to work by inhibiting photosynthesis, with strong inhibition of alanine aminotransferase and aspartate aminotransferase.[7]

Kochia control

Kochia was the hardest weed to control in sugarbeet around Colorado, Nebraska, Montana and Wyoming. It can emerge at any time while growing sugar beet, and grows 6 inches to 6 feet high. Benzadox came as a breakthrough since it could be applied to weeds post-emergently and selectively on sugarbeet. Selectivity on sugarbeet had been difficult, as kochia belongs to the same chenopodiaceae family.[6]

Applied to sugar-plots in 1967 and 1968, benzadox improved yields from 740, and 2250 lbs/ac. in an unweeded control, to 960 and 3640 lb/ac with 1 lb/ac. of benzadox, up to 4860 and 7920 lb/ac. with 4 lb/ac. of benzadox. No benzadox treated plot had as high a yield as the hand-weeded plot, at 7020 and 8990 lb/ac., due to some weeds persisting and benzadox's crop injury at higher rates to the sugarbeet. The sugar content as a percentage was notably higher in the plots which were hand-weeded or treated with 2 lb/ac. or more of benzadox, because of the reduced competition from weeds.[6]

Rain shortly after herbicide application reduced the effectiveness to virtually nothing, though rain 8 hours after application had relatively little effect. Higher temperature, 70°F compared to 55°F, increased crop injury a lot, though weed control was unaffected.[6]

Commercialisation

It has been manufactured by Murphy Chemical Co and DowElanco.[2]

"Topcide" was a brand name of Gulf Oil Corporation, Agricultural Chemicals Division, with 22.5% benzadox-ammonium by weight, or 2 pounds per US gallon, recommending 1 gallon per acre to be sprayed, (2 lbs per acre active ingredient, or 2.24 kg/Ha) from a tractor sprayer. The 1970 version of the label says control is reduced if the temperature is below 55°F (13°C) or if it rains within 8 hours of spraying. Weeds turn brown within 2 to 5 days, and temporary yellowing or stunning of beets might occur. The mixture was not to be mixed with other herbicides.[8]

References

  1. ^ a b c "BCPC - Benzadox". www.bcpcpesticidecompendium.org. Retrieved 8 February 2026.
  2. ^ a b c d e Hertfordshire, University of. "Benzadox (Ref: MC0035)". sitem.herts.ac.uk. Pesticide Properties Database. Retrieved 8 February 2026.
  3. ^ a b c "Benzadox". pubchem.ncbi.nlm.nih.gov. PubChem. Retrieved 8 February 2026.
  4. ^ a b c d e f Informatics, NIST Office of Data and. "Acetic acid, [(benzoylamino)oxy]-". webbook.nist.gov. Retrieved 8 February 2026.
  5. ^ a b c d "Safety data sheet according to 1907/2006/EC, Article 31". www.lgcstandards.com. LGC. 18 December 2019. Retrieved 8 February 2026.
  6. ^ a b c d Weatherspoon, D. M.; Schweizer, E. E. (1970). "Control of Kochia in Sugarbeets with Benzadox". Weed Science. 18 (1): 183–185. ISSN 0043-1745. Retrieved 8 February 2026.
  7. ^ Nakamoto, Hitoshi; Ku, Maurice S. B.; Edwards, Gerald E. (1982). "Inhibition of C4 photosynthesis by (benzamidooxy)acetic acid". Photosynthesis Research. 3 (4): 293–305. doi:10.1007/BF00034110.
  8. ^ "Gulf Topcide Post-Emergence Herbicide" (PDF). www3.epa.gov. Gulf Oil Corporation. 8 January 1970. Retrieved 8 February 2026.
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