Naproanilide |
![]() Last updated: 23/02/2021 |
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(Also known as: naproanalide; BRN 2746253) |
SUMMARY |
Naproanilide is a rice herbicide not used in the EU. It itself has no herbicidal activity however its major metabolite 2-(2-naphthoxy)propionic acid does. It is only slightly toxic. Photodegradation appears to be the main degradation pathway in paddy fields. Little is known about naproanilides toxicity to wildlife. |
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A selective herbicide used for the control of weeds in rice paddy fields. | |
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Broad-leaved weeds; Annual and perennial Cyperaceous weeds | |
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Rice | |
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Unknown | |
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circa 1981 |
UK regulatory status |
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Not approved | ||
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Not applicable | ||
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No UK approval for use |
EC Regulation 1107/2009 (repealing 91/414) |
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Not approved | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Not applicable | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Not applicable | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Not applicable | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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No | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Also used in |
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Chemical structure |
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Naproanilide is a chiral molecule and the technical material is an isomeric mixture of the S- and R-isomeric forms. The R-form exhibits the strongest herbicidal activity and is around 8x more effective than the S-form. | |
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C₁₉H₁₇NO₂ | |
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CC(C(=O)NC1=CC=CC=C1)OC2=CC3=CC=CC=C3C=C2 | |
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No data | |
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LVKTWOXHRYGDMM-UHFFFAOYSA-N | |
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InChI=1S/C19H17NO2/c1-14(19(21)20-17-9-3-2-4-10-17)22-18-12-11-15-7-5-6-8-16(15)13-18/h2-14H,1H3,(H,20,21) | |
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Yes |
General status |
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Herbicide | |
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Anilide | |
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Synthetic | |
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Stimulates RNA synthesis. Absorbed through stems and roots. No herbicidal activity itself but is rapidly hydrolysed to an active metabolite | |
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52570-16-8 | |
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None allocated | |
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40413 | |
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291.34 | |
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rac-(2R)-2-(naphthalen-2-yloxy)-N-phenylpropanamide | |
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(RS)-α-2-naphthoxypropionanilide | |
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2-(2-naphthalenyloxy)-N-phenylpropanamide | |
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K3 | |
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15 | |
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Not applicable | |
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Not applicable | |
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- | |
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Colourless crystalline substance |
Formulations |
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Often supplied as a soluble concentrate that is mixed with water and used as a spray |
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0.75 | Q3 Q = Miscellaneous internet resources at 27 °C3 = Unverified data of known source |
Low | ||||||||
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171000 | E3 E = Manufacturers safety data sheets Acetone3 = Unverified data of known source |
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42000 | E3 E = Manufacturers safety data sheets Toluene3 = Unverified data of known source |
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17000 | E3 E = Manufacturers safety data sheets Ethanol3 = Unverified data of known source |
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128 | V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source |
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2.00 X 1003 | Calculated | - | |||||||
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3.3 | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
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1.256 | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
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Not applicable | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
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No dissociation | |||||||||||
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3.0 X 10-06 | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
Low volatility | ||||||||
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Degradation |
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0.1 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
Non-persistent | |||||||
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0.1 | R3 R = Peer reviewed scientific publications 3 = Unverified data of known source |
Non-persistent | ||||||||
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Substance rapidly degrades to its major metabolite | ||||||||||
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Soil adsorption and mobility |
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- | Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source |
Moderately mobile | |||||||
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Fate indices |
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-1.43 | Calculated | Low leachability | ||||||||||||||||||||||||||
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8.27 X 10-06 | Calculated | - | |||||||||||||||||||||||||
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Low | Calculated | - | ||||||||||||||||||||||||||
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Moderately mobile | Calculated | - |
Key metabolites |
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Soil | 1.00 | Not assessed under 91/414 or 1107/2009 |
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> 2710 | V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) Rat3 = Unverified data of known source |
Low | ||||||||
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3.5 | Q3 Q = Miscellaneous internet resources Cyprinus carpio3 = Unverified data of known source |
Moderate | ||||||||
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General |
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High (class III) | - | - | ||||||||
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> 2710 | V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) Rat3 = Unverified data of known source |
Low | ||||||||
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5000 | V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) Rat3 = Unverified data of known source |
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1.67 | V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) Rat3 = Unverified data of known source |
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Health issues |
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No further information available |
Handling issues |
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When heated to decomposition it emits toxic vapors of NOx | |||
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Health: H313 | |||
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III (Slightly hazardous) | |||
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naproanilide | ||
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Record last updated: | 23/02/2021 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |