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United States Patent (19) 11 4,027,037 Siegle Et Al

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United States Patent (19) 11 4,027,037 Siegle Et Al United States Patent (19) 11 4,027,037 Siegle et al. (45) May 31, 1977 (54) N-SUBSTITUTED B-AMINOCROTONIC 57) ABSTRACT ACID ESTERS N-substituted (3-aminocrotonic acid esters of the for mula (75) Inventors: Peter Siegle, Cologne; Klaus Sasse, Schildgen; Peter Rössler, Cologne, all of Germany CH. COOR: (I) RC=CCN H (73) Assignee: Bayer Aktiengesellschaft, R11 Leverkusen, Germany in which (22 Filed: Mar. 12, 1975 R is hydrogen, or alkyl or alkenyl with up to 4 car bon atoms, (21) Appl. No.: 557,698 R’ is straight-chain or branched alkyl or alkenyl with up to 9 carbon atoms, optionally interrupted by O 30 Foreign Application Priority Data or S, and optionally substituted by halogen, phe Mar. 26, 1974 Germany .......................... 2414456 noxy, dimethylamino, cyclic alkyl or alkenyl with up to 8 carbon atoms which are optionally substi (52) U.S. C. ......................... 424/314; 260/239 BE; tuted by halogen, dimethylamino, or alkyl, alkoxy 260/239 BF; 260/247.2 B; 260/268 R; or alkylthio with up to 4 carbon atoms, phenyl 260/293.88; 260/326.43; 260/340.5; which is optionally substituted by halogen, dimeth 260/347.4; 260/468 G; 260/468 J; 260/470; ylamino, phenoxy, or alkyl, alkenyl, acyl, alkoxy, 260/471 A; 260/479 S; 260/481 R; 260/482 alkenoxy or alkynoxy containing up to 4 carbon R; 424/244; 424/2 48.52; 424/250; 424/267; atoms, or a 5- or 6-membered heterocyclic ring 424/274; 424/282; 424/285; 424/299; containing at least one O, S or N hetero-atom and 424/309; 424/248.55 optionally substituted by halogen, alkyl or alkoxy containing up to 4 carbon atoms or R is further (51 int. C.’.................. C07C 101/28: A01N 9/20 more cyclic alkyl or alkenyl with up to 8 carbon 58) Field of Search ................. 260/482 R. 424/314 atoms optionally substituted by halogen, dimethyl amino, or alkyl, alkoxy or alkylthio with up to 4 (56) References Cited carbon atoms; phenyl optionally substituted by UNITED STATES PATENTS halogen, dimethylamino, phenoxy, or alkyl, alke 2,578,788 12/1951 Benneville ..................... 260/482 R nyl, acyl, alkoxy, alkenoxy or alkynoxy containing 2,588,696 2/1952 Dickey .............................. 424/314 up to 4 carbon atoms; or a 5- or 6-membered het 2,852,527 9/1958 Steck ....... ... 260/482 R erocyclic ring containing at least one O, S or N 2,976,285 3/1961 Gash ........ ... 260/471 A heteroatom and optionally substituted by halogen, 2,987,491 6/1961 Bader ............................ 260/482 R or alkyl or alkoxy containing up to 4 carbon atoms; 3,265,698 8/1966 Allen et al. ..... ... 260/326.12 R O 3,420,827 1/1969 Leffingwell .................... 260/482 R R" and R together with the adjoining nitrogen atom FOREIGN PATENTS OR APPLICATIONS form a heterocyclic structure optionally substi tuted by lower alkyl with 1-4 carbon atoms and 1,120,802 12/1961 Germany optionally containing further heteroatoms in addi OTHER PUBLICATIONS tion to nitrogen, and R’ is straight-chain or branched alkyl, alkenyl or Sonnet, J.Agr. Food Chem., 2001), pp. 65-69, (1972). alkynyl each with up to 10 carbon atoms, or cyclic Nilies, J. Agr. Food. Chem., 21 (3), pp. 342-347, alkyl or alkenyl with up to 8 carbon atoms, option (1973). ally substituted by halogen, alkoxy or alkyl-thio Allen et al. II, J.A.C.S., 88, pp. 2536-2544, (1966). containing up to 4 carbon atoms, phenyl, 3,4- Allen et al., Beilstein, vol. 4, p. 467, (1922). methylenedioxyphenyl, cyclic alkyl or alkenyl with Allen et al., Beilstein, 1st Supp., vol. 4, pp. 889-890, up to 8 carbon atoms; phenyl optionally substi (1943). tuted by dioxymethylene or alkyl, alkenyl, alkynyl, Allen et al., Beilstein, 2nd Supp., vol. 4, pp. alkoxy, alkenoxy, alkynoxy or acyl containing up 1495-1496, (1963). to 4 carbon atoms; or a heterocyclic ring contain Arnold, Chem. Abst. 62:1 1672-3 (1965). ing up to 6 atoms of which at least one is O, N or Krasnaya, Chem. Abst. 78:71347q (1973). S, which ring is optionally bonded via alkyl con Wright, Chem. Abst., 81:22188s (1974). taining up to 4 carbon atoms, Primary Examiner-Lorraine A. Weinberger which inhibit the metamorphosis of arthropods. Assistant Examiner-Michael Shippen Attorney, Agent, or Firm-Burgess, Dinklage & Sprung 9 Claims, No Drawings 4,027,037 1 2 R is straight-chain or branched alkyl or alkenyl with N-SUBSTITUTED B-AMINOCROTONIC ACID up to 10 carbon atoms, optionally interrupted by O ESTERS or S, and optionally substituted by halogen, phe The present invention relates to and has for its ob noxy, dimethylamino, cyclic alkyl or alkenyl with jects the provision of particular new N-substituted g 5 up to 8 carbon atoms which are optionally substi aminocrotonic acid esters which inhibit the metamor tuted by halogen, dimethylamino, or alkyl, alkoxy phosis of arthropods, active compositions in the form. or alkylthio with up to 4 carbon atoms, phenyl of mixtures of such compounds with solid and liquid which is optionally substituted by halogen, dimeth dispersible carrier vehicles, and methods for producing ylamino, phenoxy, or alkyl, alkenyl, acyl, alkoxy, such compounds and for using such compounds in a 10 alkenoxy or alkynoxy containing up to 4 carbon new way especially for combating arthropods, e.g. in atoms, or a 5- or 6-membered heterocyclic ring sects and acarids, with other and further objects be containing at least one O, S or N hetero-atom and coming apparent from a study of the within specifica optionally substituted by halogen, alkyl or alkoxy tion and accompanying examples. containing up to 4 carbon atoms or cyclic alkyl or The inhibition of metamorphosis to which this speci 15 alkenyl with up to 8 carbon atoms optionally sub fication refers involves affecting the developmental stituted by halogen, dimethylamino, or alkyl, alk metabolism of arthropods, by, for example, preventing oxy or alkylthio with up to 4 carbon atoms; phenyl the ecdysis of larvae, the transformation to the pupa or optionally substituted by halogen, dimethylamino, to the imago, the deposition of eggs capable of develop phenoxy, or alkyl, alkenyl, acyl, alkoxy, alkenoxy ment, or the development of eggs which have been laid. 20 or alkynoxy containing up to 4 carbon atoms; or a This interrupts the generation cycle and reduces the 5- or 6-membered heterocyclic ring containing at population of the arthropods. This interference with least one O, S or N heteroatom and optionally development prevents the treated organisms from ma substituted by halogen, or alkyl or alkoxy contain turing and becoming capable of reproduction. ing up to 4 carbon atoms; or 25 R and R together with the adjoining nitrogen atom It is generally know that conventional animal bio form a heterocyclic structure optionally substituted cides, for example phosphoric acid esters, when used as by lower alkyl with 1-4 carbon atoms and option ingested poisons and contact poisons, kill both verte ally containing further heteroatoms in addition to brates and invertebrates through cholinesterase-inhibi nitrogen, and tion. Furthermore, it is already known that, in contrast 30 R is straight-chain or branched alkyl, alkenyl or to these conventional biocides which act as contact alkynyl each with up to 10 carbon atoms, or cyclic poisons or ingested poisons and kill the animals in a few alkyl or alkenyl with up to 8 carbon atoms, option hours, a juvenile hormone, or substances chemically ally substituted by halogen, alkoxy or alkyl-thio closely related to this hormone can be used to prevent containing up to 4 carbon atoms, phenyl, 3,4- the development of insects and spider mites, especially 35 methylenedioxyphenyl, cyclic alkyl or alkenyl with in the final phase of the development of pupae, or up to 8 carbon atoms; phenyl optionally substituted sexually mature imagos (J. J. Menn and M. Beroza: by dioxymethylene or alkyl, alkenyl, alkynyl, alk Insect Juvenilhormones, Chemistry & Action, Acade oxy, alkenoxy, alkynoxy or acyl containing up to 4 mie Press, New York 1972). carbon atoms; or a heterocyclic ring containing up For this reason, a large number of investigations have 40 to 6 atoms of which at least one is O, N or S, which concerned themselves with the chemical modification ring is optionally bonded via alkyl containing up to of the natural hormones. These investigations showed, 4 carbon atoms. in particular, that a fairly long unsaturated alkyl chain Preferably, R is hydrogen, alkyl or alkenyl with up to is responsible for good hormone activity (H.J. Zabiket 3 carbon atoms, especially methyl, ethyl or allyl; R is al., J.Agr. Food Chem. 21, 342 (1973)). 45 straight-chain or branched alkyl with up to 9 carbon Thus it has been found that g-aminocrotonic acid atoms which can optionally be substituted by norbor esters with citronellylamine or epoxycitronellylamine nyl, morpholine, chlorine, phenoxy, cyclohexyloxy, as the amino component are good juvenile hormone cyclohexy, cyclohexenyl, methylcyclohexenyl, furfuryl analogues (P. E. Sonnet et al., J.Agr. Food Chem. 20, or dimethylamine and can be interrupted one or more 65 (1972)). , , , , 50 times by O or S, or R’ is cyclopentyl, cyclohexyl, cy Further, it has been disclosed that g-aminocrotonic cloheptyl or cyclooctyl which are optionally substituted acid esters with long-chain amino groups and/or ester by methyl, isopropyl, methoxy or ethoxy, or allyl, or groups are good fungicides and acaricides (compare phenyl which is optionally substituted by chlorine, bro German Auslegeschrift (German Published Specifica mine, methyl, ethyl, ethoxy, allyloxy, propargyloxy, tion) 1,120,802). 55 dimethylamino, phenoxy or acetyl, or benzyl which is However, it is a disadvantage of these compounds optionally substituted by chlorine or ethyl; or RandR that the starting materials are too expensive, and that and the adjoining nitrogen atom form an optionally some of them can only be prepared with difficulty.
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