Structure-activity relationship study of alkynyl ether insecticide synergists and the development of MB-599 (verbutin).
Structure-activity relationships of aryl alkynyl synergists of the general formula of Ar-Q-R, where Q represents a bridging structure, were studied using a standardised testing system and Relative Potency values. Ethers, esters, oxime ethers, amides and amines were prepared and evaluated. The length of the R-alkynyl chain, the role of the bridge and the substitution of the aromatic ring were examined systematically. The most potent compounds possessed an aromatic ring connected via a bridge of three atoms to an alkynyl chain, forming together a linear side-chain of six atoms. Several highly potent compounds were synthesised of which one (MB-599; proposed common name verbutin) was selected for development as a selective insecticide synergist in crop protection. Its high potential at practical insecticide:synergist ratios makes possible the reduction of the total amount of insect-control chemicals applied, and its use as an additive to produce new formulations of existing insecticides makes it highly advantageous in resistance management, giving a new tool to sustain the effectiveness of a wide range of insecticides. A product containing a (1+1) mixture of verbutin and beta-cypermethrin was launched in Hungary in 2002.
Bertók
Béla
B
Agro-Chemie Pesticide Manufacturing Trading and Distributing Co Ltd, 1225 Budapest, Bányalég u. 2, Hungary. bertokb@elender.hu
Pap
László
L
Arvai
Géza
G
Bakonyvári
Ildikó
I
Kuruczné Ribai
Zsuzsanna
Z
D000480:Alkynes / Q000138:chemical synthesis* / Q000633:toxicity; D000577:Amides / Q000138:chemical synthesis; D000588:Amines / Q000138:chemical synthesis; D000818:Animals; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000633:toxicity; D002235:Carbofuran / Q000633:toxicity; D004357:Drug Synergism; D004952:Esters / Q000138:chemical synthesis; D004987:Ethers / Q000138:chemical synthesis; D006793:Houseflies / Q000187:drug effects; D007305:Insecticide Resistance; D007306:Insecticides / Q000138:chemical synthesis* / Q000633:toxicity; D015394:Molecular Structure; D010091:Oximes / Q000138:chemical synthesis; D010574:Pesticide Synergists / Q000138:chemical synthesis* / Q000633:toxicity; D011722:Pyrethrins / Q000138:chemical synthesis / Q000633:toxicity; D021281:Quantitative Structure-Activity Relationship
D000480:Alkynes; D000577:Amides; D000588:Amines; D001555:Benzene Derivatives; D004952:Esters; D004987:Ethers; D007306:Insecticides; D010091:Oximes; D010574:Pesticide Synergists; D011722:Pyrethrins; C432908:verbutin; C017160:cypermethrin; D002235:Carbofuran