NOVEL HETEROARYL-TRIAZOLE AND HETEROARYL-TETRAZOLE COMPOUNDS AS PESTICIDES
20210386070 · 2021-12-16
Inventors
- Alexander ARLT (Koeln, DE)
- Werner Hallenbach (Nordhorn, DE)
- Hans-Georg SCHWARZ (Doesten, DE)
- Martin FUESSLEN (Duesseldorf, DE)
- Heinz-Juergen Wroblowsky (Langenfeld, DE)
- Estella VUSCATO ARSEQUELL (Frankfurt am Main, DE)
- Marc LINKA (Duesswldorf, DE)
- Kerstin ILG (Koeln, DE)
- Arunas DAMIJONAITIS (Leverkusen, DE)
- Ulrich Ebbinghaus-Kintscher (Dortmund, DE)
- Ulrich Goergens (Ratingen, DE)
- Yolanda Cancho Grande (Leverkusen, DE)
- peter JESCHKE (Bergusch Gladbach, DE)
- Juachim TELSER (Wuppertal, DE)
- Iring HEISLER (Duesseldorf, DE)
- Andreas Turberg (Haan, DE)
Cpc classification
C07D403/04
CHEMISTRY; METALLURGY
C07D413/04
CHEMISTRY; METALLURGY
A01N43/82
HUMAN NECESSITIES
C07D401/04
CHEMISTRY; METALLURGY
C07D409/04
CHEMISTRY; METALLURGY
C07D417/04
CHEMISTRY; METALLURGY
A01N43/00
HUMAN NECESSITIES
International classification
A01N43/82
HUMAN NECESSITIES
C07D401/04
CHEMISTRY; METALLURGY
C07D403/04
CHEMISTRY; METALLURGY
C07D409/04
CHEMISTRY; METALLURGY
C07D413/04
CHEMISTRY; METALLURGY
C07D417/04
CHEMISTRY; METALLURGY
Abstract
The present invention relates to novel heteroaryl-triazole and heteroaryl-tetrazole compounds of the general formula (I), in which the structural elements Y, Q.sup.1, Q.sup.2, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning given in the description, to formulations and compositions comprising such compounds and for their use in the control of animal pests including arthropods and insects in plant protection and to their use for control of ectoparasites on animals.
##STR00001##
Claims
1. A compound of formula (I) ##STR00199## in which X is O or S; Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond or CH.sub.2; R.sup.1 is hydrogen; C.sub.1-C.sub.6alkyl optionally substituted with one substituent selected from —CN, —CONH.sub.2, —COOH, —NO.sub.2 and —Si(CH.sub.3).sub.3; C.sub.1-C.sub.6haloalkyl; C.sub.2-C.sub.6alkenyl; C.sub.2-C.sub.6haloalkenyl; C.sub.2-C.sub.6alkynyl; C.sub.2-C.sub.6haloalkynyl; C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl- wherein the C.sub.3-C.sub.4cycloalkyl is optionally substituted with one or two halogen atoms; oxetan-3-yl-CH.sub.2— or benzyl optionally substituted with halogen atoms or C.sub.1-C.sub.3haloalkyl; R.sup.2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X-group, each independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, halogen, —NO.sub.2, —SF.sub.5, —CN, —CONH.sub.2, —COOH and —C(S)NH.sub.2; R.sup.3 is C.sub.1-C.sub.3alkyl or C.sub.1-C.sub.3haloalkyl; R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2, substituted C.sub.3-C.sub.4cycloalkyl; and C.sub.1-C.sub.3alkyl and C.sub.1-C.sub.3alkoxy, both substituted by one to three substituents independently selected from the group consisting of —NH.sub.2, —OH, —NO.sub.2, —CN, —SH, CO.sub.2C.sub.1-C.sub.4alkyl, —CONH.sub.2, SF.sub.5, —SO.sub.2NH.sub.2, C.sub.3-C.sub.4cycloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.5-C.sub.6cycloalkenyl, C.sub.2-C.sub.4alkynyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, N—C.sub.1-C.sub.4alkanoylamino, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.2-C.sub.4alkenyloxy, C.sub.2-C.sub.4alkynyloxy, C.sub.3-C.sub.4cycloalkoxy, C.sub.5-C.sub.6cycloalkenyloxy, C.sub.1-C.sub.4alkoxycarbonyl, C.sub.2-C.sub.4alkenyloxycarbonyl, C.sub.2-C.sub.4alkynyloxycarbonyl, C.sub.6-,C.sub.10-,C.sub.14-aryloxycarbonyl, C.sub.1-C.sub.4alkanoyl, C.sub.2-C.sub.4alkenylcarbonyl, C.sub.2-C.sub.4alkynylcarbonyl, C.sub.6-,C.sub.10-,C.sub.14-arylcarbonyl, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4haloalkylthio, C.sub.3-C.sub.4cycloalkylthio, C.sub.2-C.sub.4alkenylthio, C.sub.5-C.sub.6cycloalkenylthio, C.sub.2-C.sub.4alkynylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4haloalkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4haloalkylsulfonyl, —SO.sub.2—NH(C.sub.1-C.sub.6alkyl), —SO.sub.2—N(C.sub.1-C.sub.6alkyl).sub.2, C.sub.1-C.sub.4alkylphosphinyl, C.sub.1-C.sub.4alkylphosphonyl, N—C.sub.1-C.sub.4alkylaminocarbonyl, N,N-di-C.sub.1-C.sub.4alkylaminocarbonyl, N—C.sub.1-C.sub.4alkanoylaminocarbonyl, N—C.sub.1-C.sub.4alkanoyl-N—C.sub.1-C.sub.4alkylaminocarbonyl, C.sub.6-,C.sub.10-,C.sub.14-aryl, C.sub.6-,C.sub.10-,C.sub.14-aryloxy, benzyl, benzyloxy, benzylthio, C.sub.6-,C.sub.10-,C.sub.14-arylthio, C.sub.6-,C.sub.10-,C.sub.14-arylamino, benzylamino, heterocyclyl, heteroaryl and trialkylsilyl, and substituents bonded via a double bond, optionally C.sub.1-C.sub.4alkylidene (optionally methylidene or ethylidene), an oxo group, an imino group and a substituted imino group; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.5-C.sub.6cycloalkyl, C.sub.4-C.sub.6alkyl, C.sub.4-C.sub.6haloalkyl, C.sub.4-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —NHCO—C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; and the other one to two optional substituent(s) are each independently selected from group B consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2; and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —SO.sub.2NH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; R.sup.5 is hydrogen, halogen, —CN, or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkoxy, —C(O)C.sub.1-C.sub.6alkoxy, —CH(C.sub.1-C.sub.6alkoxy).sub.2, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —C(═NOC.sub.1-C.sub.6alkyl)H, or —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl.
2. The compound according to claim 1, in which X is O or S; Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond or CH.sub.2; R.sup.1 is hydrogen; C.sub.1-C.sub.6alkyl optionally substituted with one substituent selected from —CN, —CONH.sub.2, —COOH, —NO.sub.2 and —Si(CH.sub.3).sub.3; C.sub.1-C.sub.6haloalkyl; C.sub.2-C.sub.6alkenyl; C.sub.2-C.sub.6haloalkenyl; C.sub.2-C.sub.6alkynyl; C.sub.2-C.sub.6haloalkynyl; C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl- wherein the C.sub.3-C.sub.4cycloalkyl is optionally substituted with one or two halogen atoms; oxetan-3-yl-CH.sub.2— or benzyl optionally substituted with halogen atoms or C.sub.1-C.sub.3haloalkyl; R.sup.2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X-group, each independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, halogen, —NO.sub.2, —SF.sub.5, —CN, —CONH.sub.2, —COOH and —C(S)NH.sub.2; R.sup.3 is C.sub.1-C.sub.3alkyl or C.sub.1-C.sub.3haloalkyl; R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —NH.sub.2, C.sub.1-C.sub.6alkyl, optionally substituted C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.1-C.sub.4alkoxy; or R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —NH.sub.2, C.sub.5-C.sub.6cycloalkyl, substituted C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —NHCO—C.sub.1-C.sub.4haloalkyl, —NHCO—C.sub.1-C.sub.4cyanoalkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, halogen, C.sub.1-C.sub.3alkyl and C.sub.2-C.sub.4haloalkenyl; —NHCO—C.sub.1-C.sub.4alkyl-C.sub.3-C.sub.6cycloalkyl, —NHCO-phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of halogen, CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl; —N(SO.sub.2C.sub.1-C.sub.3alkyl).sub.2, —NH(SO.sub.2C.sub.1-C.sub.3alkyl), —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —NHSO.sub.2C.sub.1-C.sub.4haloalkyl, —NHCS—C.sub.1-C.sub.4alkyl, —NHCS—C.sub.3-C.sub.5cycloalkyl, —NHCS—C.sub.1-C.sub.4alkyl-C.sub.3-C.sub.5cycloalkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.5alkyl), wherein the alkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C.sub.1-C.sub.4alkyl).sub.2, —CONH—C.sub.3-C.sub.5cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C.sub.1-C.sub.5alkyl)(C.sub.3-C.sub.5cycloalkyl), CONH-phenyl, wherein the phenyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CONHSO.sub.2—C.sub.1-C.sub.4alkyl, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.1-C.sub.4alkoxy; the other one to two optional substituent(s) are each independently selected from group B consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.1-C.sub.4alkoxy; or R.sup.4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —NH.sub.2, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.1-C.sub.4alkoxy; or R.sup.4 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NH(C.sub.1-C.sub.4alkyl), —N(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.3haloalkyl and C.sub.1-C.sub.4alkoxy; R.sup.5 is hydrogen, halogen, —CN, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, —C(O)C.sub.1-C.sub.3alkoxyC, —CH(C.sub.1-C.sub.3alkoxy).sub.2, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —C(═NOC.sub.1-C.sub.4alkyl)H, or —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl.
3. The compound according to claim 1, in which X is O or S; Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q and Q.sup.2 is N; Y is a direct bond or CH.sub.2; R.sup.1 is hydrogen; C.sub.1-C.sub.3alkyl optionally substituted with one substituent selected from —CN, —CONH.sub.2, —COOH, —NO.sub.2 and —Si(CH.sub.3).sub.3; C.sub.1-C.sub.3haloalkyl; C.sub.2-C.sub.4alkenyl; C.sub.2-C.sub.4haloalkenyl; C.sub.2-C.sub.4alkynyl; C.sub.2-C.sub.4haloalkynyl; C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl- wherein the C.sub.3-C.sub.4cycloalkyl is optionally substituted with one or two halogen atoms; oxetan-3-yl-CH.sub.2—; or benzyl optionally substituted with halogen atoms or C.sub.1-C.sub.3haloalkyl; R.sup.2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X-group, each independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, halogen, —NO.sub.2, —SF.sub.5, —CN, —CONH.sub.2, —COOH and —C(S)NH.sub.2; R.sup.3 is C.sub.1-C.sub.3alkyl or C.sub.1-C.sub.3haloalkyl; R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl; or R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of —CONH.sub.2, —CN, —NO.sub.2, —NH.sub.2, C.sub.5-C.sub.6cycloalkyl, substituted C.sub.3-C.sub.4cycloalkyl, C.sub.1-C.sub.4haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, —NHCO—C.sub.1-C.sub.4haloalkyl, —NHCO—C.sub.1-C.sub.4cyanoalkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, halogen, C.sub.1-C.sub.3alkyl and C.sub.2-C.sub.4haloalkenyl; —NHCO—C.sub.1-C.sub.3alkyl-C.sub.3-C.sub.4cycloalkyl, —NHCO-phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine and chlorine; —N(SO.sub.2C.sub.1-C.sub.3alkyl).sub.2, —NH(SO.sub.2C.sub.1-C.sub.3alkyl), —NHSO.sub.2C.sub.1-C.sub.4haloalkyl, —NHCS—C.sub.1-C.sub.4alkyl, —NHCS—C.sub.3-C.sub.5cycloalkyl, —NHCS—C.sub.1-C.sub.4alkyl-C.sub.3-C.sub.5cycloalkyl, —CO.sub.2C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.5alkyl), wherein the alkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C.sub.1-C.sub.4alkyl).sub.2, —CONH—C.sub.3-C.sub.5cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CON(C.sub.1-C.sub.5alkyl)(C.sub.3-C.sub.5cycloalkyl), CONH-phenyl, wherein the phenyl is optionally substituted with one to three substituents selected from the group consisting of cyano and halogen; —CONHSO.sub.2—C.sub.1-C.sub.4alkyl-C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl; the other one to two optional substituent(s) are each independently selected from group B consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl; or R.sup.4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl or R.sup.4 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), —CN, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, C.sub.1-C.sub.3alkylthio, C.sub.1-C.sub.3alkylsulfinyl, C.sub.1-C.sub.3alkylsulfonyl, C.sub.3-C.sub.4cycloalkylsulfanyl, C.sub.3-C.sub.4cycloalkylsulfinyl, C.sub.3-C.sub.4cycloalkylsulfonyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3haloalkylsulfinyl, C.sub.1-C.sub.3haloalkylsulfonyl, —NHCO—C.sub.1-C.sub.4alkyl, —N(C.sub.1-C.sub.4alkyl)CO—C.sub.1-C.sub.4alkyl, —CONH(C.sub.1-C.sub.4alkyl), —CON(C.sub.1-C.sub.4alkyl).sub.2, —C(═NOC.sub.1-C.sub.4alkyl)H, —C(═NOC.sub.1-C.sub.4alkyl)-C.sub.1-C.sub.4alkyl; and phenyl and 5- to 6-membered heteroaryl, wherein the phenyl or 5- to 6-membered heteroaryl is optionally substituted with one to two substituents, each independently selected from the group consisting of halogen, —CN, C.sub.1-C.sub.6alkyl and C.sub.1-C.sub.3haloalkyl; R.sup.5 is hydrogen, halogen, —CN, C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.3-C.sub.4cycloalkyl, or C.sub.1-C.sub.3alkoxy.
4. The compound according to claim 1, in which X is O or S; Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond or CH.sub.2; R.sup.1 is hydrogen; C.sub.1-C.sub.3alkyl optionally substituted with —CN, —Si(CH.sub.3).sub.3 or one to three substituents selected from the group consisting of fluorine, chlorine or bromine; C.sub.2-C.sub.4alkenyl; C.sub.2-C.sub.4alkynyl; or C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl- wherein the C.sub.3-C.sub.4cycloalkyl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine and bromine; R.sup.2 is phenyl or pyridine, wherein the phenyl or pyridine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X group, each independently selected from the group consisting of fluorine, chlorine, bromine, —CN, —NO.sub.2, —SF.sub.5, methyl, difluoromethyl, trifluoromethyl, heptafluoropropyl, methoxy, trifluoromethoxy, difluoromethoxy, difluoromethylthio, and trifluoromethylthio; R.sup.3 is C.sub.1-C.sub.3alkyl; R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl; or R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of —CONH.sub.2, —CN, —NO.sub.2, —NH.sub.2, cyclopentyl, cyclohexyl, trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2,3,3,3-pentafluoropropoxy, 4,4,4-trifluorobutoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl, methoxyiminomethyl, —NHCO—C.sub.1-C.sub.3alkyl, —NHCO—C.sub.1-C.sub.3haloalkyl, —NHCO—C.sub.1-C.sub.3cyanoalkyl, —NHCO—C.sub.3-C.sub.5cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, fluorine, chlorine, methyl and C.sub.2-C.sub.4haloalkenyl; —NHCO—C.sub.1-C.sub.3alkyl-C.sub.3-C.sub.4cycloalkyl, —NHCO— phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine and chlorine; —N(SO.sub.2C.sub.1-C.sub.3alkyl).sub.2, —NHSO.sub.2C.sub.1-C.sub.3alkyl, —NHSO.sub.2C.sub.1-C.sub.3haloalkyl, —NHCS—C.sub.1-C.sub.3alkyl, —NHCS—C.sub.3-C.sub.4cycloalkyl, —NHCS—C.sub.1-C.sub.3alkyl-C.sub.3-C.sub.4cycloalkyl, —CONH(C.sub.1-C.sub.5alkyl), wherein the alkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, fluorine and chlorine; —CON(C.sub.1-C.sub.3alkyl).sub.2, —CONH—C.sub.3-C.sub.4cycloalkyl, wherein the cycloalkyl is optionally substituted with one to three substituents selected from the group consisting of cyano, fluorine and chlorine; —CON(C.sub.1-C.sub.3alkyl)(C.sub.3-C.sub.4cycloalkyl), —CONH-phenyl, wherein the phenyl is optionally substituted with one to three substituents selected from the group consisting of cyano, fluorine and chlorine; —CONHSO.sub.2—C.sub.1-C.sub.3alkyl, —CO.sub.2C.sub.1-C.sub.4alkyl; and phenyl and 5-membered heteroaryl, wherein the phenyl or 5-membered heteroaryl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl; the other one to two optional substituents are each independently selected from group B consisting of fluorine, chlorine, bromine, iodine, —CN, methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl; or R.sup.4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, —CN, methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl; or R.sup.4 is a heterocyclic ring which is selected from the group consisting of 5-membered saturated or partially unsaturated heterocyclyl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of fluorine, chlorine, bromine, iodine, ═O (oxo), —CN, methyl, cyclopropyl, difluoromethyl, trifluoromethyl, methoxy, trifluoromethoxy, difluoromethoxy, methylthio, methylsulfinyl, methylsulfonyl, difluoromethylthio, difluoromethylsulfinyl, difluoromethylsulfonyl, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfonyl and phenyl, wherein the phenyl is optionally substituted with one to two substituents selected from the group consisting of fluorine, chlorine, bromine, —CN, difluoromethyl and trifluoromethyl; R.sup.5 is hydrogen, fluorine, chlorine, bromine, —CN, methyl, ethyl, propyl, iso-propyl, difluoromethyl, trifluoromethyl, cyclopropyl, methoxy, or ethoxy.
5. The compound according to claim 1, in which X is O or S; Q.sup.1 is N; Q.sup.2 is CR.sup.5; Y is a direct bond; R.sup.1 is hydrogen, ethyl, cyclopropyl-CH.sub.2—, 2-trimethylsilylethyl or 2,2,2-trifluoroethyl; R.sup.2 3-chloro-5-(trifluoromethyl)phenyl, 3-cyano-5-fluorophenyl, 3-fluoro-5-(trifluoromethyl)phenyl, 3,4,5-trifluorophenyl, 4-chloro-3,5-difluorophenyl, 3-methyl-5-(trifluoromethyl)phenyl, 3-chloro-5-(trifluoromethoxy)phenyl, 3-chloro-5-(trifluoromethylthio)phenyl, 3-bromo-5-chlorophenyl, 3,5-dichlorophenyl, 3-chloro-5-(pentafluoro-A6-sulfanyl)phenyl, 3,5-bis(trifluoromethyl)phenyl, 5-bromopyridin-3-yl, 5-iodopyridin-3-yl, 5-(trifluoromethyl)pyridin-3-yl, 3-chloro-5-methoxyphenyl, 3-bromo-5-(trifluoromethyl)phenyl, 3-methoxy-5-(trifluoromethyl)phenyl, 3-chloro-5-(difluoromethoxy)phenyl, 3-bromo-5-cyanophenyl, 3-cyano-5-(trifluroromethyl), 3-bromo-5-fluorophenyl, 3-fluoro-5-(trifluoromethylthio)phenyl, 3-chloro-5-nitrophenyl, 5,6-bis(trifluoromethyl)pyridin-3-yl, 5-chloropyridin-3-yl, 3-((1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethylphenyl, 6-chloro-4-(trifluoromethyl)pyridin-2-yl, or 3-chlorophenyl; R.sup.3 is methyl or ethyl; R.sup.4 is 4,6-dimethylpyrimidin-2-yl, 4-methoxy-6-methylpyrimidin-2-yl, 1,3-thiazol-2-yl, quinoxalin-2-yl, [1,2,4]triazolo[1,5-a]pyridin-2-yl, 1-methyl-1H-pyrazol-3-yl, 5-cyanopyridin-2-yl, 5-cyanopyrimidin-2-yl, 5-(trifluoromethoxy)pyrimidin-2-yl, 5-(difluoromethoxy)pyrimidin-2-yl, 5-chloro-3-fluoropyridin-2-yl, 3,5-difluoropyridin-2-yl, 4-cyanopyridin-2-yl, 5-(trifluoromethoxy)pyridin-2-yl, 5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl, 5-chloro-4-(difluoromethyl)-1,3-thiazol-2-yl, 5-(4-fluorophenyl)-1,3,4-thiadiazol-2-yl, 1,1-dioxothiolan-3-yl, 5-(trifluoromethylthio)pyridin-2-yl, 5-(trifluoromethylsulfonyl)pyridin-2-yl, 5-nitropyridin-2-yl, 5-(difluoromethoxy)pyridin-2-yl, 5-aminopyridin-2-yl, 5-(methoxycarbonyl)pyridin-2-yl, 3-(difluoromethyl)-1-methyl-1H-pyrazol-4-yl, 5-(acetylamino)pyridin-2-yl, 5-[(cyclopropylcarbonyl)amino]pyridin-2-yl, 4-(4-chlorophenyl)-1,3-thiazol-2-yl, 5-[(4-fluorobenzoyl)amino]pyridin-2-yl, 5-[bis(methylsulfonyl)amino]pyridin-2-yl, 5-(methylcarbamoyl)pyridin-2-yl, 5-(2,2,2-trifluoroethoxy)pyridin-2-yl, 4-(2-fluorophenyl)-1,3-thiazol-2-yl, 1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl, 5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-2-yl, 4-(3-chlorophenyl)-1,3-thiazol-2-yl, 4-(4-fluorophenyl)-1,3-thiazol-2-yl, 5-(methylsulfonamido)pyridin-2-yl, 6-cyanopyridin-2-yl, 1,3-benzoxazol-2-yl, 6-(2,2,2-trifluoroethoxy)pyridin-2-yl, 5-(2,2,3,3,3-pentafluoropropoxy)pyridin-2-yl, N-cyclopropyl-pyridin-2-yl-5-carboxamide, 5-methylsulfonylpyridin-2-yl, 6-methylsulfonylpyridin-2-yl, 5-(methoxyiminomethyl)pyridin-2-yl, 5-((2,2,2-trifluoroacetyl)amino)pyridin-2-yl, 5-((2-cyanoacetyl)amino)pyridin-2-yl, 5-pyrazolylpyridin-2-yl, 4,5-dihydrothiazol-2-yl, 5-((1-cyanocyclopropylcarbonyl)amino)pyridin-2-yl, N-(2,2,2-trifluoroethyl)pyridin-2-yl-5-carboxamide, 5-bromothiazol-2-yl, 4-(trifluoromethyl)thiazol-2-yl, 5-(trifluoromethyl)thiazol-2-yl, 5-imidazolyl-pyridin-2-yl, 5-(1,2,4-triazolyl)pyridin-2-yl, 5-chlorothiazol-2-yl, 5-(trifluoromethylsulfonylamino)pyridin-2-yl, 5-((cyclopropylethylthioyl)amino)pyridin-2-yl, 5-(cyclopropylcarbothioylamino)pyridin-2-yl, 5-(2-methylpropylthioylamino)pyridin-2-yl, pyridin-2-yl-5-carboxamide, 5-((1-chlorocyclopropylcarbonyl)amino)pyridin-2-yl, N-(4-fluorophenyl)pyridin-2-yl-5-carboxamide, N-cyclopropyl-N-methyl-pyridin-2-yl-5-carboxamide, N-methylsulfonyl-pyridin-2-yl-5-carboxamide, N-(1-cyanocyclopropyl)pyridin-2-yl-5-carboxamide, 5-iodothiazol-2-yl, 4-(2,4-difluorophenyl)thiazol-2-yl, N,N-dimethyl-pyridin-2-yl-5-carboxamide, N,N-diethyl-pyridin-2-yl-5-carboxamide, N-isobutyl-pyridin-2-yl-5-carboxamide, 5-((2-cyclopropylacetyl)amino)pyridin-2-yl, 5-((2,2-difluorocyclopropylcarbonyl)amino)pyridin-2-yl, 5-((3,3-((Z)-2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2-dimethyl-cyclopropylcarbonyl)amino)pyridin-2-yl, 5-(propanoylamino)pyridin-2-yl, 5-((3-chlorobenzoyl)amino)pyridin-2-yl, 5-(4,4,4-trifluorobutoxy)pyridin-2-yl, N-ethyl-pyridin-2-yl-5-carboxamide, N-(1,2-dimethylpropyl)pyridin-2-yl-5-carboxamide, 5-((2-chlorobenzoyl)amino)pyridin-2-yl, N-cyanomethyl-pyridin-2-yl-5-carboxamide, N-(2-chlorophenyl)-pyridin-2-yl-5-carboxamide, N-(4-chlorophenyl)-pyridin-2-yl-5-carboxamide, N-(3-chlorophenyl)-pyridin-2-yl-5-carboxamide, or 4-pyrazol-1-yl-pyridin-2-yl; R.sup.5 is hydrogen, methyl, propyl or trifluoromethyl.
6. The compound according to claim 1, comprising a structure according to formula (I′) ##STR00200##
7. The compound according to claim 1, in which Q.sup.1 represents N or CR.sup.5 and Q.sup.2 represents N.
8. The compound according to claim 1, in Q.sup.1 represents N and Q.sup.2 represents CR.sup.5.
9. The compound of formula (a) ##STR00201## in which Q.sup.1 and Q.sup.2 are independently CR.sup.5 or N, provided at least one of Q.sup.1 and Q.sup.2 is N; Y is a direct bond or CH.sub.2; R.sup.1 is hydrogen; C.sub.1-C.sub.6alkyl optionally substituted with one substituent selected from —CN, —CONH.sub.2, —COOH, —NO.sub.2 and —Si(CH.sub.3).sub.3; C.sub.1-C.sub.6haloalkyl; C.sub.2-C.sub.6alkenyl; C.sub.2-C.sub.6haloalkenyl; C.sub.2-C.sub.6alkynyl; C.sub.2-C.sub.6haloalkynyl; C.sub.3-C.sub.4cycloalkyl-C.sub.1-C.sub.2alkyl- wherein the C.sub.3-C.sub.4cycloalkyl is optionally substituted with one or two halogen atoms; oxetan-3-yl-CH.sub.2— or benzyl optionally substituted with halogen atoms or C.sub.1-C.sub.3haloalkyl; R.sup.2 is phenyl, pyridine, pyrimidine, pyrazine or pyridazine, wherein the phenyl, pyridine, pyrimidine, pyrazine or pyridazine is optionally substituted with one to three substituents, provided the substituent(s) are not on either carbon adjacent to the carbon bonded to the C═X-group, each independently selected from the group consisting of C.sub.1-C.sub.3alkyl, C.sub.1-C.sub.3haloalkyl, C.sub.1-C.sub.3haloalkylthio, C.sub.1-C.sub.3alkoxy, C.sub.1-C.sub.3haloalkoxy, halogen, —NO.sub.2, —SF.sub.5, —CN, —CONH.sub.2, —COOH and —C(S)NH.sub.2: R.sup.3 is C.sub.1-C.sub.3alkyl or C.sub.1-C.sub.3haloalkyl; R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with two to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is pyridine, pyrimidine, pyrazine or pyridazine, wherein the pyridine, pyrimidine, pyrazine or pyridazine is substituted with a total of one to three substituent(s), provided at least one and up to three substituent(s) are independently selected from group A consisting of —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2, substituted C.sub.3-C.sub.4cycloalkyl; and C.sub.1-C.sub.3alkyl and C.sub.1-C.sub.3alkoxy, both substituted by one to three substituents independently selected from the group consisting of —NH.sub.2, —OH, —NO.sub.2, —CN, —SH, CO.sub.2C.sub.1-C.sub.4alkyl, —CONH.sub.2, SF.sub.5, —SO.sub.2NH.sub.2, C.sub.3-C.sub.4cycloalkyl, C.sub.2-C.sub.4alkenyl, C.sub.5-C.sub.6cycloalkenyl, C.sub.2-C.sub.4alkynyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, N—C.sub.1-C.sub.4alkanoylamino, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy, C.sub.2-C.sub.4alkenyloxy, C.sub.2-C.sub.4alkynyloxy, C.sub.3-C.sub.4cycloalkoxy, C.sub.5-C.sub.6cycloalkenyloxy, C.sub.1-C.sub.4alkoxycarbonyl, C.sub.2-C.sub.4alkenyloxycarbonyl, C.sub.2-C.sub.4alkynyloxycarbonyl, C.sub.6-,C.sub.10-,C.sub.14-aryloxycarbonyl, C.sub.1-C.sub.4alkanoyl, C.sub.2-C.sub.4alkenylcarbonyl, C.sub.2-C.sub.4alkynylcarbonyl, C.sub.6-,C.sub.10-,C.sub.14-arylcarbonyl, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4haloalkylthio, C.sub.3-C.sub.4cycloalkylthio, C.sub.2-C.sub.4alkenylthio, C.sub.5-C.sub.6cycloalkenylthio, C.sub.2-C.sub.4alkynylthio, C.sub.1-C.sub.4alkylsulfinyl, C.sub.1-C.sub.4haloalkylsulfinyl, C.sub.1-C.sub.4alkylsulfonyl, C.sub.1-C.sub.4haloalkylsulfonyl, —SO.sub.2—NH(C.sub.1-C.sub.6alkyl), —SO.sub.2—N(C.sub.1-C.sub.6alkyl).sub.2, C.sub.1-C.sub.4alkylphosphinyl, C.sub.1-C.sub.4alkylphosphonyl, N—C.sub.1-C.sub.4alkylaminocarbonyl, N,N-di-C.sub.1-C.sub.4alkylaminocarbonyl, N—C.sub.1-C.sub.4alkanoylaminocarbonyl, N—C.sub.1-C.sub.4alkanoyl-N—C.sub.1-C.sub.4alkylaminocarbonyl, C.sub.6-,C.sub.10-,C.sub.14-aryl, C.sub.6-,C.sub.10-,C.sub.14-aryloxy, benzyl, benzyloxy, benzylthio, C.sub.6-,C.sub.10-,C.sub.14-arylthio, C.sub.6-,C.sub.10-,C.sub.14-arylamino, benzylamino, heterocyclyl, heteroaryl and trialkylsilyl, and substituents bonded via a double bond, optionally C.sub.1-C.sub.4alkylidene optionally methylidene or ethylidene), an oxo group, an imino group and a substituted imino group; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.5-C.sub.6cycloalkyl, C.sub.4-C.sub.6alkyl, C.sub.4-C.sub.6haloalkyl, C.sub.4-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —NHCO—C.sub.1-C.sub.6alkyl-C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; and the other one to two optional substituent(s) are each independently selected from group B consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —NO.sub.2, —NH.sub.2; and in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is a 5-membered heteroaryl optionally substituted with one to three substituents independently selected from the group consisting of halogen, hydroxy, —CN, —COOH, —CONH.sub.2, —CSNH.sub.2, —SO.sub.2NH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S-C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; or R.sup.4 is a heterocyclic ring which is selected from the group consisting of 4- to 10-membered saturated or partially unsaturated heterocyclyl, 9-membered heteroaryl and 10-membered heteroaryl, each of which is optionally substituted by one to three substituents independently selected from the group consisting of halogen, ═O (oxo), hydroxy, —CN, —COOH, —SO.sub.2NH.sub.2, —CONH.sub.2, —CSNH.sub.2, —NO.sub.2, —SF.sub.5, —NH.sub.2; and in each case optionally substituted —CO.sub.2—C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.3-C.sub.6cycloalkyl-C.sub.1-C.sub.6alkyl, C.sub.1-C.sub.6haloalkyl, C.sub.1-C.sub.6alkoxy, C.sub.1-C.sub.6haloalkoxy, C.sub.1-C.sub.6alkylthio, C.sub.1-C.sub.6alkylsulfinyl, C.sub.1-C.sub.6alkylsulfonyl, C.sub.3-C.sub.6cycloalkylsulfanyl, C.sub.3-C.sub.6cycloalkylsulfinyl, C.sub.3-C.sub.6cycloalkylsulfonyl, C.sub.1-C.sub.6haloalkylthio, C.sub.1-C.sub.6haloalkylsulfinyl, C.sub.1-C.sub.6haloalkylsulfonyl, C.sub.2-C.sub.4alkenylsulfanyl, C.sub.2-C.sub.4alkenylsulfinyl, C.sub.2-C.sub.4alkenylsulfonyl, C.sub.2-C.sub.4alkinylsulfanyl, C.sub.2-C.sub.4alkinylsulfinyl, C.sub.2-C.sub.4alkinylsulfonyl, phenylsulfanyl, phenylsulfinyl, phenylsulfonyl, S—C.sub.1-C.sub.6alkylsulfinimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfinimidoyl, S—C.sub.2-C.sub.6alkenylsulfinimidoyl, S—C.sub.2-C.sub.6alkinylsulfinimidoyl, S-phenylsulfinimidoyl, S—C.sub.1-C.sub.6alkylsulfonimidoyl, S—C.sub.3-C.sub.6cycloalkylsulfonimidoyl, S—C.sub.2-C.sub.6alkenylsulfonimidoyl, S—C.sub.2-C.sub.6alkinylsulfonimidoyl, S-phenylsulfonimidoyl, —NH(C.sub.1-C.sub.6alkyl), —N(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CO—C.sub.1-C.sub.6alkyl, —NHCO—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CO—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CO-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CO-phenyl, —NHCO-phenyl, —N(CO—C.sub.1-C.sub.6alkyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl).sub.2, —N(CO-phenyl).sub.2, —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO—C.sub.1-C.sub.6alkyl), —N(CO—C.sub.3-C.sub.6cycloalkyl)(CO-phenyl), —N(CO—C.sub.1-C.sub.6alkyl)(CO-phenyl), —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —CONH(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.3-C.sub.6cycloalkyl).sub.2, —CONH—SO.sub.2—C.sub.1-C.sub.6alkyl, —CONH—SO.sub.2-phenyl, —CONH—SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—C.sub.1-C.sub.6alkyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2-phenyl, —CON(C.sub.1-C.sub.6alkyl)-SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —CONH-phenyl, —CON(C.sub.1-C.sub.6alkyl)phenyl, —CON(C.sub.3-C.sub.6cycloalkyl)phenyl, —N(SO.sub.2C.sub.1-C.sub.6alkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6haloalkyl).sub.2, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl).sub.2, —N(SO.sub.2C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(SO.sub.2C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2—C.sub.1-C.sub.6haloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—C.sub.1-C.sub.6alkyl, —NHSO.sub.2-phenyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2-phenyl, —NHSO.sub.2—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)SO.sub.2—(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.1-C.sub.6alkyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl).sub.2, —SO.sub.2N(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2NH(C.sub.3-C.sub.6cycloalkyl), —SO.sub.2N(C.sub.3-C.sub.6cycloalkyl).sub.2, —SO.sub.2NH(phenyl), —SO.sub.2N(C.sub.1-C.sub.6alkyl)(phenyl), —SO.sub.2N(C.sub.1-C.sub.4cycloalkyl)(phenyl), —NHCS—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CS—C.sub.1-C.sub.6alkyl, —N(C.sub.3-C.sub.6cycloalkyl)CS—C.sub.1-C.sub.6alkyl, —NHCS—C.sub.3-C.sub.6cycloalkyl, —N(C.sub.1-C.sub.6alkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.3-C.sub.6cycloalkyl)CS—(C.sub.3-C.sub.6cycloalkyl), —N(C.sub.1-C.sub.6alkyl)CS-phenyl, —N(C.sub.3-C.sub.6cycloalkyl)CS-phenyl, —NHCS-phenyl, —CSNH(C.sub.1-C.sub.6alkyl), —CSN(C.sub.1-C.sub.6alkyl).sub.2, —CSNH(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.1-C.sub.6alkyl)(C.sub.3-C.sub.6cycloalkyl), —CSN(C.sub.3-C.sub.6cycloalkyl).sub.2, —CSNH-phenyl, —CSN(C.sub.1-C.sub.6alkyl)phenyl, —CSN(C.sub.3-C.sub.6cycloalkyl)phenyl, —C(═NOC.sub.1-C.sub.6alkyl)H, —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl, phenyl and 5- to 6-membered heteroaryl; R.sup.5 is hydrogen, halogen, —CN, or in each case optionally substituted C.sub.1-C.sub.6alkyl, C.sub.3-C.sub.6cycloalkyl, C.sub.1-C.sub.6alkoxy, —C(O)C.sub.1-C.sub.6alkoxy, —CH(C.sub.1-C.sub.6alkoxy).sub.2, —CO.sub.2C.sub.1-C.sub.6alkyl, —CONH(C.sub.1-C.sub.6alkyl), —CON(C.sub.1-C.sub.6alkyl).sub.2, —NHCO—C.sub.1-C.sub.6alkyl, —N(C.sub.1-C.sub.6alkyl)CO—C.sub.1-C.sub.6alkyl, —C(═NOC.sub.1-C.sub.6alkyl)H, or —C(═NOC.sub.1-C.sub.6alkyl)-C.sub.1-C.sub.6alkyl. and wherein the compound of formula (a) is not N-{1-[1-(2,3-dihydro-1,4-benzodioxin-6-yl)-1H-tetrazol-5-yl]propyl}prop-2-yn-1-amine.
10. A compound of formula (b*) ##STR00202## in which E is trifluoromethoxy or difluoromethoxy; A is methylsulfonyl or hydrazinyl; and wherein the compound of formula (b*) is not 5-(difluoromethoxy)-2-(methylsulfonyl)pyrimidine.
11. A compound comprising 5-(difluoromethoxy)-2-hydrazinopyridine and/or a salt thereof.
12. A formulation, optionally an agrochemical formulation, comprising at least one compound of formula (I) according to claim 1.
13. The formulation according to claim 12, further comprising at least one extender and/or at least one surface-active substance.
14. The formulation according to claim 12, wherein the compound of formula (I) is in a mixture with at least one further active compound.
15. Method for controlling one or more pests, optionally animal pests, comprising allowing a compound of formula (I) according to claim 1 or a formulation thereof to act on the pests and/or a habitat thereof.
16. Method according to claim 15, wherein the pest is an animal pest and comprises an insect, an arachnid or a nematode, or the pest is an insect, an arachnid or a nematode.
17. A product comprising a compound of formula (I) according to claim 1 or of a formulation thereof for controlling one or more animal pests.
18. The product according to claim 17, wherein the animal pest comprises an insect, an arachnid or a nematode, or the animal pest is an insect, an arachnid or a nematode.
19. A product according to claim 17 in crop protection.
20. A product according to claim 17 in the field of animal health.
21. Method for protecting seed or a germinating plant from one or more pests, optionally animal pests, comprising contacting the seed with a compound of formula (I) according to claim 1 or with a formulation thereof.
22. Seed obtained by a method according to claim 21.
Description
PREPARATION EXAMPLES
Synthesis of 3-Chloro-N-(cyclopropylmethyl)-N-{1-[1-(4,6-dimethylpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide (Example I-002)
[0651] A solution of 70 mg (0.20 mmol)N-(1-amino-1-oxopropan-2-yl)-3-chloro-N-(cyclopropylmethyl)-5-(trifluoromethyl)benzamide and 40 μL (0.30 mmol) N,N-dimethylformamide dimethyl acetal in 2 mL dichloromethane was heated to reflux. After 2 h the reaction mixture was concentrated under reduced pressure. To the residue were added 47 mg (0.34 mmol) 2-hydrazino-4,6-dimethylpyrimidine and 2 mL acetic acid. The mixture was heated for 1 h at 80° C. The solvent was removed under reduced pressure and the residue purified by preparative HPLC (H.sub.2O/acetonitrile) to provide 69 mg of 3-chloro-N-(cyclopropylmethyl)-N-{1-[1-(4,6-dimethylpyrimidin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide.
[0652] .sup.1H-NMR (600.1 MHz, CD3CN, 260 K):
[0653] δ=8.0579 (2.6); 7.9952 (0.9); 7.8774 (0.1); 7.7920 (1.4); 7.7705 (0.1); 7.7449 (0.1); 7.5604 (0.6); 7.2792 (0.5); 7.2598 (2.3); 7.2499 (0.5); 7.2137 (1.5); 7.1595 (1.5); 7.1080 (0.8); 6.4680 (0.3); 6.4564 (0.8); 6.4448 (0.8); 6.4332 (0.3); 6.0097 (0.1); 5.9983 (0.3); 5.9868 (0.3); 5.9754 (0.1); 5.4723 (5.2); 3.8632 (0.2); 3.8531 (0.2); 3.8396 (0.2); 3.8294 (0.2); 3.6125 (0.2); 3.6005 (0.2); 3.5889 (0.2); 3.5768 (0.2); 2.8727 (0.5); 2.8614 (0.5); 2.8466 (0.7); 2.8352 (0.7); 2.7094 (0.6); 2.6997 (0.7); 2.6832 (0.5); 2.6735 (0.5); 2.5757 (0.1); 2.4963 (0.1); 2.4705 (16.0); 2.3617 (0.2); 2.3447 (5.5); 2.2921 (29.3); 2.0803 (0.1); 2.0761 (0.1); 2.0720 (0.2); 2.0679 (0.1); 2.0639 (0.1); 1.9854 (0.4); 1.9772 (0.5); 1.9694 (12.5); 1.9653 (24.3); 1.9612 (35.7); 1.9571 (24.6); 1.9530 (12.6); 1.8543 (0.1); 1.8502 (0.1); 1.8461 (0.2); 1.8420 (0.2); 1.8379 (0.1); 1.8076 (3.6); 1.7959 (3.6); 1.7307 (1.3); 1.7192 (1.2); 1.5799 (0.2); 1.5686 (0.2); 1.2604 (0.1); 1.2138 (0.2); 1.2027 (0.2); 1.1931 (0.2); 0.5692 (0.2); 0.5565 (0.4); 0.5505 (0.4); 0.5435 (0.4); 0.5378 (0.3); 0.5294 (0.3); 0.5244 (0.2); 0.5155 (0.4); 0.5050 (0.4); 0.4947 (0.4); 0.4860 (0.2); 0.4833 (0.2); 0.4733 (0.1); 0.4378 (0.2); 0.4299 (0.2); 0.4231 (0.2); 0.4155 (0.1); 0.3996 (0.1); 0.3923 (0.2); 0.3862 (0.2); 0.3783 (0.2); 0.3056 (0.2); 0.2965 (0.2); 0.2903 (0.4); 0.2825 (0.5); 0.2749 (0.4); 0.2684 (0.3); 0.2600 (0.2); 0.2349 (0.2); 0.2262 (0.4); 0.2189 (0.4); 0.2124 (0.5); 0.2046 (0.4); 0.1981 (0.2); 0.1894 (0.2); 0.0968 (0.1); 0.0053 (0.8); −0.0001 (24.6); −0.0055 (0.8); −0.1002 (0.1); −0.2220 (0.2); −0.2305 (0.4); −0.2384 (0.6); −0.2464 (0.6); −0.2544 (0.5); −0.2626 (0.2); −0.3853 (0.2); −0.3936 (0.5); −0.4016 (0.6); −0.4095 (0.5); −0.4176 (0.4); −0.4258 (0.2).
[0654] ESI mass [m/z]: 479.2 [M+H].sup.+
Synthesis of 5-(difluoromethoxy)-2-hydrazinopyrimidine
[0655] A solution of 500 mg (2.60 mmol) 5-(difluoromethoxy)-2-(methylsulfanyl)pyrimidine in 2 mL ethanol was treated with 0.52 mL (11 mmol) of hydrazine hydrate. The mixture was heated to reflux overnight. The reaction mixture was then cooled to 5° C. upon which a white precipitate formed. The suspension was filtered and the precipitate washed with ethanol. The residue was dried under reduced pressure to provide 125 mg of 5-(difluoromethoxy)-2-hydrazinopyrimidine.
[0656] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 8.35 (s, 1H), 8.28 (s, 2H), 7.06 (t, J=74 Hz, 1H), 4.17 (br s, 2H).
[0657] ESI mass [m/z]: 177.2 [M+H].sup.+
Synthesis of 2-hydrazino-5-(trifluoromethoxy)pyrimidine
Step 1: 4-(2-furyl)-2-(methylsulfanyl)-5-(trifluoromethoxy)pyrimidine
[0658] To a suspension of 40.2 g (290 mmol)S-methyl isothiourea hemisulfate in 1 L iPrOH were added under careful stirring 15.7 g (290 mmol) sodium methoxide. The mixture was stirred for 15 min at ambient temperature and 48 g (193 mmol) 3-(dimethylamino)-1-(2-furyl)-2-(trifluoromethoxy)prop-2-en-1-one (prepared as described in WO 2013/120876) were added carefully. The mixture was heated for 20 h at 60° C. and stirred for further 50 h at ambient temperature. The solvent was removed in vacuo and the residue poured onto 1 L water. After extraction with 4×100 mL diethyl ether the combined organic layers were washed with 70 mL water and dried with Na.sub.2SO.sub.4. The solvent was removed under reduced pressure, and the residue was purified by distillation. 4-(2-furyl)-2-(methylsulfanyl)-5-(trifluoromethoxy)pyrimidine was collected at 120-140° C. (1 Torr) as a yellow liquid, 20 g (38%).
[0659] .sup.1H-NMR (CDCl.sub.3, 200 MHz): 8.46 (s, 1H), 7.70 (s, 1H), 7.38 (d, J=3.5 Hz, 1H), 6.61 (d, J=1.6 Hz, 1H,), 2.61 (s, 3H).
Step 2: 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine-4-carboxylic Acid
[0660] To a solution of 41.7 g (183 mmol) H.sub.5IO.sub.6 in 170 mL water were added 183 mL 1M aq. NaOH, followed by 175 mL hexane and 175 mL EtOAc. 4.6 g (17 mmol) 4-(2-furyl)-2-(methylsulfanyl)-5-(trifluoromethoxy)pyrimidine and 0.20 g Ruthenium(III) chloride hydrate were added and the mixture was stirred for 20 h at ambient temperature. The organic layer was separated, the aq. layer saturated with solid sodium chloride and the product was extracted with 4×50 mL EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated to afford 4.0 g residue as a yellowish oil which solidified upon storage. The solid was washed with 2 mL CH.sub.2Cl.sub.2 at −30° C. to provide 2.0 g 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine-4-carboxylic acid as a yellowish powder.
[0661] .sup.1H NMR (DMSO-d.sub.6, 200.1 MHz): 9.48 (s, 1H), 3.48 (s, 3H).
Step 3: 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine
[0662] A mixture of 1.10 g (3.84 mmol) 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine-4-carboxylic acid and 4 ml anisole was heated to reflux for 1 h. The solvent was removed under reduced pressure and the residue purified by chromatography on silica to provide 759 mg 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine.
[0663] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 9.31 (s, 2H), 3.46 (s, 3H).
[0664] ESI mass [m/z]: 243.1 [M+H].sup.+
Step 4: 2-hydrazino-5-(trifluoromethoxy)pyrimidine
[0665] A solution of 759 mg (3.13 mmol) 2-(methylsulfonyl)-5-(trifluoromethoxy)pyrimidine in 3 mL methanol was treated with 0.62 mL (13 mmol) of hydrazine hydrate. The mixture was stirred for 4 h at room temperature upon which a white precipitate formed. The suspension was filtered and the precipitate washed with methanol. The residue was dried under reduced pressure to provide 490 mg of 2-hydrazino-5-(trifluoromethoxy)pyrimidine.
[0666] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 8.62 (s, 1H), 8.44 (s, 2H), 4.25 (s, 2H).
[0667] ESI mass [m/z]: 195.2 [M+H].sup.+
Synthesis of 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfonyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide (Example I-027)
Step 1: Synthesis of 2-hydrazino-5-[(trifluoromethyl)sulfanyl]pyridine
[0668] A solution of 500 mg (2.34 mmol) 2-chloro-5-[(trifluoromethyl)sulfanyl]pyridine in 1 mL ethanol was treated with 1.8 mL (37 mmol) hydrazine hydrate. The mixture was heated at reflux for 4 h and stirred over night at room temperature. The solvent was removed under reduced pressure to provide 713 mg of a residue containing 2-hydrazino-5-[(trifluoromethyl)sulfanyl]pyridine.
[0669] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 8.27 (br s, 1H), 8.17 (d, 1H), 7.67 (dd, 1H), 6.78 (d, 1H), 4.34 (br s, 2H).
[0670] ESI mass [m/z]: 210.1 [M+H].sup.+
Step 2: 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfanyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide (Example I-026)
[0671] A mixture of 270 mg (0.91 mmol)N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(trifluoromethyl)benzamide, 0.18 mL (1.35 mmol) N,N-dimethylformamide dimethyl acetal and 10 mL CH.sub.2Cl.sub.2 was heated at reflux for 2 h. All volatile components were removed under reduced pressure and the residue dissolved in 10 mL glacial acetic acid. To this solution were added 300 mg of the crude product of 2-hydrazino-5-[(trifluoromethyl)sulfanyl]pyridine obtained in the previous step. The mixture was heated at 80° C. for 2 h. The acetic acid was removed under reduced pressure and the residue purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 228 mg 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfanyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide.
[0672] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): δ=9.4031 (3.9); 9.3855 (4.0); 8.8088 (6.8); 8.8034 (6.8); 8.4426 (3.6); 8.4369 (3.4); 8.4212 (4.0); 8.4155 (3.8); 8.2355 (15.8); 8.1235 (7.4); 8.0685 (7.9); 8.0545 (7.1); 8.0417 (7.7); 8.0203 (6.8); 6.1185 (0.6); 6.1011 (2.7); 6.0837 (4.2); 6.0663 (2.7); 6.0489 (0.6); 3.5872 (0.5); 3.5815 (0.4); 3.3292 (117.7); 2.6778 (0.6); 2.6730 (0.7); 2.6690 (0.5); 2.5086 (98.8); 2.5043 (121.9); 2.5000 (87.5); 2.3353 (0.6); 2.3311 (0.8); 2.3270 (0.6); 1.6597 (16.0); 1.6424 (16.0); 1.2593 (0.4); 1.2336 (0.9); 0.0076 (1.2); −0.0002 (22.8).
[0673] ESI mass [m/z]: 496.0 [M+H].sup.+
Step 3: 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfonyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide (Example I-027)
[0674] To a solution of 72 mg (0.14 mmol) 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfanyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide in a solvent mixture of 2.8 mL CH.sub.2Cl.sub.2, 2.8 mL acetonitrile and 5.8 mL water were added 94 mg (0.43 mmol) sodium periodate followed by 0.03 mg (0.1 μmol) ruthenium (III) chloride. The reaction mixture was stirred for 6 h at room temperature before it was quenched with a saturated aqeuous solution of sodium thiosulfate. The mixture was repeatedly extracted with ethyl acetate and the combined organic layers were dried with Na.sub.2SO.sub.4. The solvent was removed under reduced pressure and the residue purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 65 mg of 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[(trifluoromethyl)sulfonyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide.
[0675] .sup.1H NMR (DMSO-d.sub.6, 600 MHz): δ=9.4305 (1.4); 9.4189 (1.4); 9.2120 (2.1); 9.2084 (2.1); 8.7877 (1.2); 8.7836 (1.2); 8.7731 (1.2); 8.7690 (1.3); 8.3335 (5.0); 8.2943 (2.3); 8.2933 (2.2); 8.2797 (2.2); 8.2787 (2.2); 8.1479 (2.3); 8.0887 (2.4); 8.0709 (2.2); 6.1710 (0.9); 6.1594 (1.5); 6.1478 (1.0); 3.3185 (16.0); 2.5241 (0.8); 2.5210 (1.0); 2.5179 (1.0); 2.5090 (16.6); 2.5060 (34.7); 2.5030 (47.8); 2.5000 (37.2); 2.4971 (19.6); 1.6703 (5.6); 1.6588 (5.7); 1.2336 (0.5); −0.0001 (6.2); −0.0056 (0.3).
[0676] ESI mass [m/z]: 527.9 [M+H].sup.+
Synthesis of 3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide (Example I-034)
Step 1: N-{(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoro-methyl)benzamide (Example I-030)
[0677] To a solution of 1.22 g (2.76 mmol) 3-chloro-N-{(1S)-1-[1-(5-nitropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide in a mixture of 65 mL ethanol and 6.4 mL acetic acid was added 0.62 g (11 mmol) iron powder. The mixture was heated at 80° C. for 2 h. All volatiles were removed under reduced pressure. Water and a saturated aqueous solution of NaHCO.sub.3 were added to the residue. The layers were separated and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried with Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to give 1.19 g of N-{(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide.
[0678] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): δ=9.3155 (3.1); 9.2973 (3.2); 8.3160 (2.3); 8.1145 (6.0); 8.0718 (6.0); 8.0489 (5.4); 8.0038 (16.0); 7.7932 (6.4); 7.7866 (6.3); 7.4056 (6.0); 7.3840 (7.0); 7.3085 (0.5); 7.1236 (4.7); 7.1165 (4.5); 7.1020 (4.1); 7.0949 (4.1); 5.7925 (0.5); 5.7754 (2.4); 5.7577 (3.7); 5.7400 (2.4); 5.7224 (0.5); 5.6711 (10.8); 4.0560 (0.9); 4.0382 (2.7); 4.0204 (2.7); 4.0026 (0.9); 3.3257 (96.9); 3.3015 (0.7); 2.6807 (0.3); 2.6762 (0.7); 2.6717 (1.0); 2.6670 (0.7); 2.6624 (0.3); 2.5251 (2.6); 2.5204 (3.7); 2.5117 (57.2); 2.5072 (118.8); 2.5027 (157.4); 2.4981 (110.6); 2.4935 (51.0); 2.3341 (0.7); 2.3295 (1.0); 2.3249 (0.7); 2.1011 (0.4); 1.9892 (12.0); 1.5794 (14.6); 1.5620 (14.4); 1.3360 (0.4); 1.2591 (0.4); 1.2497 (0.7); 1.2348 (1.3); 1.1931 (3.3); 1.1754 (6.6); 1.1576 (3.2); 0.8536 (0.4); 0.0080 (0.7); −0.0002 (24.8); −0.0085 (0.7).
[0679] ESI mass [m/z]: 411.2 [M+H].sup.+
Step 2: 3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide (Example I-034)
[0680] A solution of 150 mg (0.36 mmol)N-{(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide in 0.6 mL tetrahydrofuran was treated at 0° C. with 38 mg (0.36 mmol) cyclopropanecarbonyl chloride and 0.06 mL (0.4 mmol) triethylamine. The reaction mixture was stirred over night at room temperature. Water was added, the layers separated and the aqueous layer was extracted several times with ethyl acetate. The combined organic layers were dried with Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 132 mg of 3-chloro-N-[(1S)-1-(1-{5-[(cyclopropylcarbonyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide.
[0681] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): δ=10.6212 (3.1); 9.3426 (1.8); 9.3247 (1.9); 8.7101 (3.3); 8.7044 (3.3); 8.2495 (2.2); 8.2430 (2.1); 8.2274 (2.4); 8.2209 (2.4); 8.1074 (9.4); 8.0924 (3.3); 8.0887 (2.3); 8.0418 (6.4); 8.0395 (6.2); 7.7606 (3.6); 7.7384 (3.3); 5.9342 (1.3); 5.9166 (2.0); 5.8990 (1.3); 3.3289 (106.3); 2.6769 (0.4); 2.6722 (0.5); 2.6676 (0.4); 2.5258 (1.3); 2.5211 (2.0); 2.5124 (28.6); 2.5079 (59.4); 2.5033 (78.7); 2.4987 (55.5); 2.4941 (25.7); 2.3347 (0.3); 2.3302 (0.5); 2.3255 (0.3); 2.0755 (16.0); 1.8176 (1.1); 1.8024 (1.4); 1.7870 (1.1); 1.7712 (0.4); 1.6287 (7.6); 1.6113 (7.6); 0.8733 (1.0); 0.8630 (6.1); 0.8486 (10.9); −0.0002 (0.7).
[0682] ESI mass [m/z]: 479.1 [M+H].sup.+
Synthesis of 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-methylnicotinamide (Example I-038)
[0683] A 2 M solution of methylamine in tetrahydrofuran (0.44 mL, 0.88 mmol) was diluted with 5 mL CH.sub.2Cl.sub.2. At 0° C. were carefully added 0.44 mL (0.88 mmol) of a 2 M solution of trimethyl aluminium in toluene. The mixture was stirred for 30 min at room temperature. A solution of 200 mg (0.44 mmol) methyl 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinate in CH.sub.2Cl.sub.2 was added at 0° C. and the mixture stirred for 1 h at room temperature, 6 h at reflux and over night at room temperature. Further 0.44 mL (0.88 mmol) of a 2 M solution of methylamine in tetrahydrofuran and 0.44 mL (0.88 mmol) of a 2 M solution of trimethyl aluminium in toluene were added and the mixture heated for 9 h at reflux and over night at room temperature. The reaction mixture was carefully quenched by the addition of a 10% aqueous solution of potassium sodium tartrate. CH.sub.2Cl.sub.2 was added and the layers separated. The organic layer was dried with Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (H.sub.2O/acetonitrile) to provide 66 mg of 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-methylnicotinamide.
[0684] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): δ=9.4258 (3.0); 9.4082 (3.1); 8.9523 (5.7); 8.9479 (5.4); 8.9466 (5.4); 8.7504 (2.2); 8.7391 (2.2); 8.7284 (0.8); 8.4476 (3.9); 8.4417 (3.7); 8.4263 (4.2); 8.4204 (4.2); 8.3163 (0.8); 8.1967 (14.4); 8.1438 (5.6); 8.1071 (0.7); 8.0936 (5.8); 8.0563 (5.1); 8.0422 (0.4); 7.9733 (6.0); 7.9519 (5.5); 6.1232 (0.5); 6.1059 (2.2); 6.0885 (3.5); 6.0711 (2.2); 6.0536 (0.5); 3.3275 (130.3); 3.3030 (0.4); 2.8303 (16.0); 2.8190 (15.9); 2.6811 (0.3); 2.6768 (0.7); 2.6722 (0.9); 2.6676 (0.6); 2.6632 (0.3); 2.5256 (3.1); 2.5122 (54.2); 2.5078 (108.9); 2.5033 (142.5); 2.4987 (100.4); 2.4941 (46.7); 2.3347 (0.6); 2.3301 (0.9); 2.3255 (0.7); 2.0757 (2.5); 1.6563 (13.4); 1.6390 (13.3); 1.6114 (0.5); 0.8633 (0.4); 0.8485 (0.6); −0.0002 (2.6).
[0685] ESI mass [m/z]: 453.2 [M+H].sup.+
Synthesis of 3-chloro-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoro-methoxy)benzamide (Example I-041)
Step 1: Tert-butyl {(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate
[0686] To a solution of 2.00 g (10.6 mmol) N.sup.2-(tert-butoxycarbonyl)-L-alaninamide in 40 mL CH.sub.2Cl.sub.2 was added 2.1 mL (16 mmol) N,N-dimethylformamide dimethylacetal. The solution was heated at reflux for 2 h after which the solvent was removed under reduced pressure. The residue was dissolved in a mixture of 20 mL 1,4-dioxane and 20 mL glacial acetic acid. 1.7 g (13 mmol) 6-hydrazinonicotinonitrile was added and the mixture stirred at 50° C. for 60 min. The solvents were removed under reduced pressure, a saturated aqueous solution of NaHCO.sub.3 was added and the mixture repeatedly extracted with ethyl acetate. The combined organic layers were washed with brine, dried with Na.sub.2SO.sub.4 and the solvent was removed under reduced pressure. The residue was purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 3.0 g of tert-butyl {(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate.
[0687] [α].sub.D.sup.20=+89 (c=1.0; ethanol)
[0688] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 9.10 (s, 1H), 8.57 (dd, 1H), 8.21 (s, 1H), 8.05 (d, 1H), 7.52 (d, 1H), 5.63 (m, 1H), 1.43 (d, 3H), 1.31 (s, 9H).
[0689] ESI mass [m/z]: 259.2 [M-C.sub.4H.sub.8+H].sup.+
Step 2: 6-{5-[(1S)-1-aminoethyl]-1H-1,2,4-triazol-1-yl}nicotinonitrile Hydrochloride
[0690] To a solution of 2.9 g (9.2 mmol) tert-butyl {(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate in 40 mL 1,4-dioxane were added 23 mL of a 4 M solution of HCl in 1,4-dioxane. The mixture was stirred for 4 h at 50° C. and overnight at room temperature. The solvent was removed under reduced pressure to provide 2.81 g of a residue containing 6-{5-[(1S)-1-aminoethyl]-1H-1,2,4-triazol-1-yl}nicotinonitrile hydrochloride. This was used without further purification.
[0691] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 9.11 (d, 1H), 8.80 (br d, 3H), 8.61 (dd, 1H), 8.45 (s, 1H), 8.13 (d, 1H), 5.39 (m, 1H), 1.63 (d, 3H).
[0692] ESI mass [m/z]: 215.2 [M+H].sup.+
Step 3: 3-chloro-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoro-methoxy)benzamide (Example I-041)
[0693] A mixture of 211 mg (0.87 mmol) 3-chloro-5-(trifluoromethoxy)benzoic acid, 605 mg (1.59 mmol) 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 0.31 mL (2.4 mmol)N-Ethyldiisopropylamine and 3 mL acetonitrile was stirred for 60 min at room temperature. 200 mg of the residue containing 6-{5-[(1S)-1-aminoethyl]-1H-1,2,4-triazol-1-yl}nicotinonitrile hydrochloride from the previous step and 1 ml acetonitrile were added and the mixture stirred for 2 d at room temperature. The mixture was then diluted with acetonitrile and adsorbed onto reversed phase silica gel. Purification by reversed phase chromatography (H.sub.2O/acetonitrile) provided 198 mg 3-chloro-N-{(1S)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethoxy)benzamide.
[0694] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): δ=9.3719 (3.1); 9.3545 (3.2); 9.0610 (5.4); 9.0593 (6.0); 9.0556 (5.9); 9.0537 (5.7); 8.5843 (5.2); 8.5788 (4.9); 8.5629 (5.5); 8.5573 (5.5); 8.3160 (1.0); 8.2462 (16.0); 8.0840 (6.3); 8.0822 (6.4); 8.0626 (5.9); 8.0607 (6.0); 7.9588 (4.8); 7.9546 (7.4); 7.9507 (5.1); 7.7824 (4.4); 7.7325 (4.5); 7.7299 (4.8); 7.7272 (4.0); 6.1038 (0.5); 6.0863 (2.4); 6.0689 (3.8); 6.0516 (2.4); 6.0340 (0.5); 3.3243 (352.4); 2.6802 (1.1); 2.6757 (2.4); 2.6710 (3.4); 2.6665 (2.4); 2.6619 (1.1); 2.5246 (10.1); 2.5199 (14.8); 2.5112 (196.8); 2.5067 (404.5); 2.5021 (530.9); 2.4975 (372.2); 2.4929 (172.6); 2.3380 (1.1); 2.3335 (2.4); 2.3289 (3.3); 2.3243 (2.4); 2.3197 (1.1); 2.0745 (0.4); 1.6382 (14.6); 1.6208 (14.6); 0.1459 (2.5); 0.0080 (20.9); −0.0001 (646.4); −0.0086 (19.8); −0.1496 (2.5).
[0695] ESI mass [m/z]: 437.2 [M+H].sup.+
Synthesis of 3-chloro-N-[(1S)-1-{1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide (Example I-039)
Step 1: N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(trifluoromethyl)benzamide
[0696] 5.6 g (45 mmol) L-alaninamide-hydrochloride, 10.05 (45 mmol) 3-chloro-5-(trifluoromethyl)benzoic acid and 15 ml triethylamine were stirred in 300 ml DMF at ice-water cooling. To the mixture were added 30 ml of T3P (cyclic propanphosphonic acid anhydride) 50% in EtOAc during 30 min. In the course of the next two days further 6 ml of the T3P solution were added in portions of 3 ml. To the mixture was added aq. citric acid, then the volatiles were removed under reduced pressure. The residue was dissolved in EtOAc and water. The organic layer was extracted with aq. citric acid and two times with aq. K.sub.2CO.sub.3, dried with aq. NaCl and Na.sub.2SO.sub.4 and evaporated to provide 12.63 g (95%) (95 N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(trifluoromethyl)benzamide.
[0697] ESI mass [m/z]: 293.1 [M−H].sup.−
[0698] ESI mass [m/z]: 295.1 [M+H].sup.+
[0699] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 1.3 (d, 3H), 4.4 (m, 1H), 7.0 (s, 1H), 7.45 (s, 1H), 8.1 (s, 1H), 8.2 (s, 1H), 8.25 (s, 1H), 8.9 (d, 1H).
Step 2: N-{(1S)-1-[1-(5-bromopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide
[0700] 3.22 g (11 mmol)N-[(2S)-1-amino-1-oxopropan-2-yl]-3-chloro-5-(trifluoromethyl)benzamide and 10 ml (75 mmol) N,N-dimethylformamide dimethylacetal were heated at reflux in 60 ml THF for 1 h. The solution was evaporated under reduced pressure. 2.07 g (11 mmol) 5-bromo-2-hydrazinopyridine and 50 ml AcOH were added and the resulting mixture was stirred at 110° C. for 1 h, then evaporated under reduced pressure. The residue was dissolved in EtOAc, aq. K.sub.2CO.sub.3 and aq. NaCl. The 1 aqueous layer was extracted two times with EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated. Chromatography of the residue (silica 60, petrol ether/acetone) provided 3.29 g (63%). Washing with methyl tert-butyl ether and drying provided 2.75 g (51%) of N-{(1S)-1-[1-(5-bromopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide.
[0701] ESI mass [m/z]: 475.9 [M+H].sup.+
[0702] .sup.1H NMR (DMSO-d.sub.6, 400 MHz): 1.6 (d, 3H), 6.0 (m, 1H), 7.8 (m, 1H), 8.1 (br, 2H), 8.15 (s, 1H), 8.2 (s, 1H), 8.3 (dd, 1H), 8.7 (s, 1H), 9.4 (d, 1H).
Step 3: 3-chloro-N-[(1S)-1-{1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide (Example I-039)
[0703] A mixture of 1.0 g (2.1 mmol)N-{(1S)-1-[1-(5-bromopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide, 0.2 g (1 mmol) copper(I) iodide, 0.2 g (0.7 mmol) (E,E)-N,N′-cyclohexane-1,2-diylbis[1-(pyridin-2-yl)methanimine and 1.0 g (7.2 mmol) K.sub.2CO.sub.3 in 20 ml trifluoroethanol was stirred under argon at slight reflux for 3 days. The mixture was evaporated under reduced pressure and to the residue were added EtOAc and aq. solution of ethylendiaminetretraacetic acid tetrasodium salt. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated under reduced pressure. Chromatography of the residue (silica 60, petrol ether/acetone, then silica RP-18, water/acetone/0.1% HCOOH) provided 0.24 g (23%) 3-chloro-N-[(1S)-1-{1-[5-(2,2,2-trifluoroethoxy)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide.
[0704] ESI mass [m/z]: 494.1 [M+H].sup.+
[0705] .sup.1H NMR: see NMR peak list
Synthesis of 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide (Example I-045)
[0706] A mixture of 0.5 g (1.05 mmol)N-{(1S)-1-[1-(5-bromopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide, 0.2 g (1 mmol) copper(I) iodide, 0.2 g (0.7 mmol) (E,E)-N,N′-cyclohexane-1,2-diylbis[1-(pyridin-2-yl)methanimine, 0.5 g (3.7 mmol) 3-(trifluoromethyl)-1H-pyrazole and 2.0 g (14.5 mmol) K.sub.2CO.sub.3 in 50 ml 1,4-dioxane was stirred under argon in a thick-walled reaction tube with over-pressure relief valve at 140° C. for 3 days. The mixture was evaporated under reduced pressure and to the the residue were added EtOAc and aq. solution of ethylendiaminetretraacetic acid tetrasodium salt. The layers were separated and the aqueous phase was extracted three times with EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated under reduced pressure. Chromatography of the residue (silica 60, petrol ether/acetone) provided 0.32 g (51%) 3-chloro-5-(trifluoromethyl)-N-[(1S)-1-(1-{5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]benzamide.
[0707] ESI mass [m/z]: 530.0 [M+H].sup.+
[0708] .sup.1H NMR: see NMR peak list
Synthesis 3-chloro-N-[(1S)-1-(1-{5-[(methoxyimino)methyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide (Example I-065)
Step 1: 3-chloro-N-[(1S)-1-{1-[5-(hydroxymethyl)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide
[0709] A solution of 200 mg (0.44 mmol) methyl 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinate in 7 mL CH.sub.2Cl.sub.2 was cooled to −78° C. using a dry ice bath. 0.53 mL (0.53 mmol) of a 1 M solution of hydrido(diisobutyl)aluminium in CH.sub.2Cl.sub.2 was added dropwise. The reaction mixture was stirred overnight during which time the dry ice bath expired and the reaction mixture warmed up to room temperature. Then another 0.53 mL (0.53 mmol) of a 1M solution of hydrido(diisobutyl)aluminium in CH.sub.2Cl.sub.2 were added and the reaction mixture was stirred at room temperature. For workup the reaction mixture was cooled to 0° C. and quenched by the careful addition of several drops of acetone followed an aqueous saturated solution of sodium potassium tartrate. The mixture was stirred for 60 min at room temperature, CH.sub.2Cl.sub.2 was added and the layers were separated. The aqueous layer was extracted several times with ethyl acetate. The combined organic layers were washed with brine, dried with Na.sub.2SO.sub.4, filtered and concentrated. The residue was purified by preparative HPLC (H.sub.2O/acetonitrile) to provide 12 mg of 3-chloro-N-[(1S)-1-{1-[5-(hydroxymethyl)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide.
[0710] ESI mass [m/z]: 426.3 [M+H].sup.+
Step 2: 3-chloro-N-{(1S)-1-[1-(5-formylpyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide
[0711] To a solution of 11 mg (26 μmol) 3-chloro-N-[(1S)-1-{1-[5-(hydroxymethyl)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]-5-(trifluoromethyl)benzamide in 0.5 mL CH.sub.2Cl.sub.2 were added at 0° C. 14 mg (33 gmol) 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one. The mixture was stirred for 2 h at room temperature. Another 22 mg (52 gmol) 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one were added and the reaction mixture was stirred until almost complete conversion of the starting material was observed. A saturated aqueous solution of Na.sub.2S.sub.2O.sub.3 and a saturated aqueous solution of NaHCO.sub.3 were added and the mixture stirred for 15 min at room temperature. CH.sub.2Cl.sub.2 was added and the layers were separated. The aqueous layer was extracted several times with CH.sub.2Cl.sub.2. The combined organic layers were washed with brine, dried with Na.sub.2SO.sub.4, filtered and concentrated to provide 10 mg of 3-chloro-N-{(1S)-1-[1-(5-formylpyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide.
[0712] ESI mass [m/z]: 424.1 [M+H].sup.+
Step 3: 3-chloro-N-[(1S)-1-(1-{5-[(methoxyimino)methyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide (Example I-065)
[0713] To a solution of 10 mg of 3-chloro-N-{(1S)-1-[1-(5-formylpyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide in a mixture of 0.06 mL THF and 0.01 mL water were added 16 mg of a 25-30% aqueous solution of O-methylhydroxylamine hydrochloride (1:1) and 5 μL pyridine. The reaction mixture was stirred overnight at room temperature. It was then concentrated and the residue was purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 4 mg of 3-chloro-N-[(1S)-1-(1-{5-[(methoxyimino)methyl]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]-5-(trifluoromethyl)benzamide.
[0714] ESI mass [m/z]: 453.2 [M+H].sup.+
[0715] .sup.1H NMR (DMSO-d.sub.6, 400 MHz) see NMR peaklist in table 1.
Synthesis of 3-chloro-N-{(1S)-1-[1-(6-cyano-3-pyridinyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide (Example I-066)
Step 1: 2-[6-cyano-3-pyridinyl]hydrazide-2,2,2-trifluoro-ethanimidic Acid
[0716] To 1.00 g (7.10 mmol) 5-hydrazinyl-2-pyridinecarbonitrile in methanol (10 mL) 1.83 g (9.94 mmol) 2,2, 2-trifluoro-ethanimidic acid ethyl ester (purity: 76.5%) was added, and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was then stirred with n-hexane (30 mL) and ethyl acetate (3 mL). The brownish precipitate was separated and dried to obtain 1.6 g (yield: 96.7%) 2-[6-cyano-3-pyridinyl]hydrazide-2,2,2-trifluoro-ethanimidic acid.
[0717] ESI mass [m/z]: 230.1 [M+H].sup.+
Step 2: 2-[(1S)-1-[3-(trifluoromethyl)-1-(6-cyano-3-pyridinyl)-1H-1,2,4-triazol-5-yl)ethyl]-1H-isoindole-1,3(2H)-dione
[0718] To 1.55 g (6.80 mmol) 2-[6-cyano-3-pyridinyl]hydrazide-2,2,2-trifluoro-ethanimidic acid in pyridine (20 mL), 1.61 g (6.80 mmol) (αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetyl chloride (see preparation from (αS)-1,3-dihydro-α-methyl-1,3-dioxo-2H-isoindole-2-acetic acid (Pht-Ala-OH purchased from ABCR) and oxalyl chloride: D. A. Gruzdev et al., Tetrahedron: Asymmetry, 21(8), 936-942, 2010) was added, and the reaction mixture was stirred at room temperature overnight. Then water (200 mL) was added and the mixture was extracted with dichloromethane (200 mL). The organic phase was shaken out twice with saturated sodium hydrogencarbonat solution (100 mL) and separated. After drying the solvent was evaporated. The remaining solid residue was chromatographed with a cyclohexane/acetone gradient on silica gel to afford 627 mg (purity: 100%; yield: 22.3%) of the title compound as a colorless solid.
[0719] ESI mass [m/z]: 413.2 [M+H].sup.+
[0720] .sup.13C-NMR with .sup.1H dec. (CPD) (150 MHz, DMSO-d.sub.6, ppm) δ=17.2 (H.sub.3C); 43.8 (CH); 109.5 (C, pyridinyl); 115.9 (CN, pyridinyl); 117.2 (C—H, pyridinyl); 119.1 (F.sub.3C, triazolyl); 123.4 (2×C—H, phtalyl); 131.0 (2×C, phthalyl); 134.9 (2×C—H, phthalyl); 144.3 (C—H, pyridinyl); 151.0 (C, pyridinyl); 151.8 (CN, pyridinyl); 151.9 (C, triazolyl); 158.1 (C, triazolyl); 166.8 (2×C═O, phthalyl).
Step 3: 6-{5-[(1S)-1-aminoethyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl}nicotinonitrile
[0721] To 910 mg (2.21 mmol) 2-[(1S)-1-[3-(trifluoromethyl)-1-(1-(6-cyano-3-pyridinyl)-1H-1,2,4-triazol-5-yl)ethyl]-1H-isoindole-1,3(2H)-dione in ethanol (15 mL), 502 mg (5.52 mmol) hydrazine-hydrate was added, and the reaction mixture was heated under reflux. After 30 minutes a colorless precipitate was formed. The reaction mixture was stirred and heated under reflux one additional hour, aceton (15 mL) was added and the heating was continued for further 30 minutes. The reaction mixture was concentrated and the solid residue was treated with ethanol. Then, the solvent was evaporated to afford 630 mg (purity: 76%; yield: 76.9%) 6-{5-[(1S)-1-aminoethyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl}nicotinonitrile, which was used for the N-acylation reaction (step 4) without purification.
[0722] ESI mass [m/z]: 283.0 [M+H].sup.+
Step 4: 3-chloro-N-{(1S)-1-[1-(6-cyano-3-pyridinyl)-3-(trifluoromethyl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide (Example I-066)
[0723] To 282 mg (1 mmol) 6-{5-[(1S)-1-aminoethyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl}nicotinonitrile, 231.5 mg (1 mmol) 3-chloro-5-(trifluoromethyl)-benzoic acid, 168 mg (1.30 mmol) N,N-diisopropylethylamine (Hünig's Base) in N,N-dimethylformamide (DMF) (5 mL), 456.3 mg (1.20 mmol) [O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-hexafluorophosphate] (HATU) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the solid residue was treated with dichloromethane and then extracted with a saturated NaHCO.sub.3 solution and water. The organic phase was separated, dried and the solvent was evaporated. The remaining solid residue was chromatographed with a cyclohexane/acetone gradient on silica gel to afford after stir out with diethyl ether 226 mg (purity: 100%; yield: 46.2%) of the title compound.
[0724] ESI mass [m/z]: 489.0 [M+H].sup.+
[0725] .sup.1H NMR (DMSO-d.sub.6, 400 MHz) see NMR peaklist in table 1.
Synthesis of 3-chloro-N-{(1R)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzenecarbothioamide (Example I-80)
[0726] A solution of 50 mg (0.11 mmol) 3-chloro-N-{(1R)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide in 2.4 ml toluene was treated with 48 mg (0.11 mmol) of Lawesson's reagent and then the mixture was stirred 3 h at 110° C. The reaction mixture was cooled to room temperature and a saturated aqueous solution of Na.sub.2CO.sub.3 was added and then the mixture was extracted several times with EtOAc. The combine organic layers were washed with a saturated aqueous solution of Na.sub.2CO.sub.3, with brine, dried with Na.sub.2SO.sub.4, filtered and concentrated under reduced pressure to give 49 mg of 3-chloro-N-{(1R)-1-[1-(5-cyanopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzenecarbothioamide.
[0727] ESI mass [m/z]: 437.1 [M+H].sup.+
[0728] .sup.1H NMR (DMSO-d.sub.6, 400 MHz) see NMR peaklist in table 1.
Synthesis of 3-chloro-N-{(1S)-1-[1-(1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide (Example I-082)
[0729] 1.95 g (5.6 mmol) of crude 3-chloro-N-[(2S)-1-{(E)-[(dimethylamino)methylene]amino}-1-oxopropan-2-yl]-5-(trifluoromethyl)benzamide (see WO2017/192385) and 0.7 g (6.1 mmol) 2-hydrazino-1,3-thiazole were stirred in 40 ml AcOH at 110° C. for 1 h. The mixture was evaporated under reduced pressure. The residue was dissolved in EtOAc, aq. K.sub.2CO.sub.3 and aq. NaCl. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated to provide 2.31 g crude product. Chromatography with petrol ether/acetone on silica gel, evaporation, washing with petrol ether and drying provided 1.27 (55%) of the title compound.
[0730] ESI mass [m/z]: 402.2 [M+H].sup.+
[0731] .sup.1H NMR see NMR peaklist in table 1
Synthesis of N-{(1S)-1-[1-(5-bromo-1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-3-chloro-5-(trifluoromethyl)benzamide (Example I-083)
[0732] 0.26 g (0.6 mmol) of 3-chloro-N-{(1S)-1-[1-(1,3-thiazol-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}-5-(trifluoromethyl)benzamide and 0.4 g (2.4 mmol)N-bromo-succinimide were dissolved in 20 ml DMF and left overnight. Aq. sodium bisulfite was added. The mixture was evaporated under reduced pressure. The residue was dissolved in EtOAc, aq. K.sub.2CO.sub.3 and aq. NaCl. The aqueous layer was extracted three times with EtOAc. The combined organic layers were dried with Na.sub.2SO.sub.4 and evaporated to provide 0.39 g crude product. Chromatography with petrol ether/acetone on silica gel provided 0.23 g (74%) of the title compound.
[0733] ESI mass [m/z]: 482.1 [M+H].sup.+
[0734] .sup.1H NMR see NMR peaklist in table 1
Synthesis of Tert-butyl [(1S)-1-(1-{5-[(2-cyclopropylethanethioyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]carbamate)
Step 1: Tert-butyl {(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate
[0735] A mixture of 900 mg (2.69 mmol) tert-butyl {(1S)-1-[1-(5-nitropyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate and 90 mg of 10% Pd/C in ethanol (9 mL) was stirred under hydrogen (atmospheric pressure) at room temperature for 2 h. The reaction mixture was filtered through celite, and the solvent was concentrated to give 850 mg (100% yield) of tert-butyl {(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate
[0736] ESI mass [m/z]: 305.1 [M+H].sup.+
Step 2: Tert-butyl [(1S)-1-{1-[5-(2-cyclopropylacetamido)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]carbamate
[0737] To a solution of 400 mg (1.31 mmol) tert-butyl {(1S)-1-[1-(5-aminopyridin-2-yl)-1H-1,2,4-triazol-5-yl]ethyl}carbamate in 3.6 mL anhydrous tetrahydrofurane was added 0.20 mL (1.46 mmol) triethylamine. The mixture was cooled at 0° C. and then 156 mg (1.31 mmol) of cyclopropylacetyl chloride were added and the reaction was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted several times with EtOAc. The combined organic layers were washed with an aqueous 5% NaH.sub.2PO.sub.4 solution, brine and finally dried over Na.sub.2SO.sub.4 and filtered. The solvent was concentrated in vacuo to give 436 mg of tert-butyl [(1S)-1-{1-[5-(2-cyclopropylacetamido)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]carbamate (84% yield).
[0738] ESI mass [m/z]: 387.2 [M+H].sup.+
Step 3: Tert-butyl [(1S)-1-(1-{5-[(2-cyclopropylethanethioyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]carbamate
[0739] A solution of 436 mg (1.12 mmol) tert-butyl [(1S)-1-{1-[5-(2-cyclopropylacetamido)pyridin-2-yl]-1H-1,2,4-triazol-5-yl}ethyl]carbamate in 14.5 ml toluene was treated with 456 mg (1.12 mmol) of Lawesson's reagent and then the mixture was stirred 3 h at 110° C. The reaction mixture was cooled to room temperature, a saturated aqueous solution of Na.sub.2CO.sub.3 was added and then the mixture was extracted several times with EtOAc. The combined organic layers were washed with a saturated aqueous solution of Na.sub.2CO.sub.3, with brine, dried over Na.sub.2SO.sub.4, filtered and concentrated under vacuo. The residue was purified by flash chromatography to provide 252 mg (55% yield) of tert-butyl [(1S)-1-(1-{5-[(2-cyclopropylethanethioyl)amino]pyridin-2-yl}-1H-1,2,4-triazol-5-yl)ethyl]carbamate.
[0740] ESI mass [m/z]: 403.2 [M+H].sup.+
Synthesis of 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-cyclopropyl-N-methylnicotinamide (Example I-110)
Step 1: 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinic Acid
[0741] To a solution of 120 mg (0.26 mmol) methyl 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinate in 1.1 mL methanol were added 0.74 mL (0.74 mmol) of a 1 M aqueous solution of sodium hydroxide. The mixture was stirred for 1 h at room temperature and then concentrated under reduced pressure. The residue was acidified with 1 M hydrochloric acid and the mixture repeatedly extracted with ethyl acetate. The combined organic layers were dried with Na.sub.2SO.sub.4, filtered and concentrated to provide 100 mg of 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinic acid.
[0742] ESI mass [m/z]: 440.2 [M+H].sup.+
Step 2: 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-cyclopropyl-N-methylnicotinamide (Example I-110)
[0743] To a solution of 200 mg (0.45 mmol) 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)nicotinic acid and 32 mg (0.45 mmol)N-methylcyclopropanamine in 1.7 mL acetonitrile were added 0.15 mL (1.2 mmol) N,N-diisopropylethylamine and 302 mg (0.79 mmol) [0-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium-hexafluorophosphate] (HATU). The reaction mixture was stirred at room temperature overnight. It was then concentrated and the residue was purified by reversed phase chromatography (H.sub.2O/acetonitrile) to provide 220 mg 6-(5-{(1S)-1-[3-chloro-5-(trifluoromethyl)benzamido]ethyl}-1H-1,2,4-triazol-1-yl)-N-cyclopropyl-N-methylnicotinamide.
[0744] ESI mass [m/z]: 493.2 [M+H].sup.+
[0745] .sup.1H NMR (DMSO-d.sub.6, 400 MHz) see NMR peaklist in table 1
[0746] Analytical Data of the Compounds
[0747] The determination of [M+H].sup.+ or M.sup.− by LC-MS under acidic chromatographic conditions was done with 1 ml formic acid per liter acetonitrile and 0.9 ml formic acid per liter Millipore water as eluents. The column Zorbax Eclipse Plus C18 50 mm*2.1 mm was used. The temperature of the column oven was 55° C.
[0748] Instruments:
[0749] LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager autosampler. Linear gradient 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow 0.85 ml/min.
[0750] LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD, HTS PAL autosampler. Linear gradient 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow 1.0 ml/min.
[0751] The determination of [M+H].sup.+ by LC-MS under neutral chromatographic conditions was done with acetonitrile and Millipore water containing 79 mg/l ammonia carbonate as eluents.
[0752] Instruments:
[0753] LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN autosampler (column Waters Acquity 1.7 μm 50 mm*2.1 mm, oven temperature 45° C.). Linear gradient 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow 0.7 ml/min.
[0754] LC-MS5: Agilent 1100 LC system with MSD mass spectrometer and HTS PAL autosampler (column: Zorbax XDB C18 1.8 μm 50 mm*4.6 mm, oven temperature 55° C.). Linear gradient 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow 2.0 ml/min.
[0755] The log P values reported in the tables and preparation examples above were determined in accordance with EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C18). Temperature 43° C. The calibration is effected with unbranched alkan-2-ones (having 3 to 16 carbon atoms), for which the log P values are known.
[0756] Optical rotations were measured using a Perkin Elmer model 341 polarimeter at a wavelength of 589 nm, a pathlength of 10 cm and a temperature of 20° C. They are reported as specific rotations including the concentration “c” of the measured compound (in g/100 mL) and the solvent used.
[0757] The determination of the .sup.1H NMR data was effected with a Bruker Avance III 400 MHz equipped with a 1.7 mm TCI cryo probe, a Bruker Avance TH 600 MHz equipped with a 5 mm multi-nuclear cryo probe or a Bruker Avance NEO 600 MHz equipped with a 5 mm TCJ cryo probe with tetramethylsilane as reference (0.0) and the solvents CD.sub.3CN, CDCl.sub.3 or D.sub.6-DMSO.
[0758] The NMR data of selected examples are listed either in conventional form (6 values, multiplet splitting, number of hydrogen atoms) or as NMR peak lists.
[0759] NMR Peak List Method
[0760] The .sup.1H NMR data of selected examples are stated in the form of .sup.1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The pairs of δ value-signal intensity numbers for different signal peaks are listed with separation from one another by semicolons.
[0761] The peak list for one example therefore takes the form of:
[0762] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)
[0763] The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.
[0764] For calibration of the chemical shift of .sup.1H NMR spectra, we use tetramethylsilane and/or the chemical shift of the solvent, particularly in the case of spectra which are measured in DMSO. Therefore, the tetramethylsilane peak may but need not occur in NMR peak lists.
[0765] The lists of the .sup.1H NMR peaks are similar to the conventional .sup.1H NMR printouts and thus usually contain all peaks listed in a conventional NMR interpretation.
[0766] In addition, like conventional .sup.1H NMR printouts, they may show solvent signals, signals of stereoisomers of the target compounds which are likewise provided by the invention, and/or peaks of impurities.
[0767] In the reporting of compound signals within the delta range of solvents and/or water, our lists of .sup.1H NMR peaks show the standard solvent peaks, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water, which usually have a high intensity on average.
[0768] The peaks of stereoisomers of the target compounds and/or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of >90%).
[0769] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in identifying reproduction of our preparation process with reference to “by-product fingerprints”.
[0770] A person skilled in the art calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to the peak picking in question in conventional .sup.1H NMR interpretation.
[0771] Further details of .sup.1H NMR peak lists can be found in the Research Disclosure Database Number 564025.
[0772] The compounds according to the invention described in table 1 below are likewise preferred compounds of the formula (I) according to the invention which are obtained according to or analogously to the preparation examples described above.
##STR00030##
TABLE-US-00005 TABLE 1 ESI mass Example Structure NMR Peaklist.sup.1) [m/z].sup.2) I-001
TABLE-US-00006 TABLE 2 (Intermediates) ESI mass Example Structure NMR [m/z].sup.1) b*-001
Biological Examples
[0773] Ctenocephalides felis—In-Vitro Contact Tests Adult Cat Flea
[0774] 9 mg compound is solved in 1 ml acetone and diluted with acetone to the desired concentration. 250 μl of the test solution is filled in 25 ml glass test tubes and homogeneously distributed on the inner walls by rotation and tilting on a shaking device (2 h at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm.sup.2 and a homogeneous distribution, a dose of 5 μg/cm.sup.2 is achieved.
[0775] After the solvent has evaporated, each test tube is filled with 5-10 adult cat fleas (Ctenocephalides felis), closed with a perforated lid and incubated in a lying position at room temperature and relative humidity. After 48 hours efficacy is determined. The fleas are patted on the ground of the tubes and are incubated on a heating plate at 45-50° C. for at most 5 minutes. Immotile or uncoordinated moving fleas, which are not able to escape the heat by climbing upwards, are marked as dead or moribund.
[0776] A compound shows a good efficacy against Ctenocephalides felis, if at a compound concentration of 5 μg/cm.sup.2 an efficacy of at least 80% is monitored. An efficacy of 100% means all fleas are dead or moribund; 0% means no fleas are dead or moribund.
[0777] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-003, I-007, I-009, I-010, I-011, I-012, I-015, I-018, I-019, I-033, I-034, I-037, I-041, I-046, I-047, I-048, I-049, I-056, I-061, I-067, I-077, I-080, I-085, I-088, I-089.
[0778] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-042, I-052, I-078, I-079, I-081, I-082, I-083.
[0779] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-071, I-074.
[0780] Rhipicephalus sanguineus—In-Vitro Contact Tests with Adult Brown Dog Ticks
[0781] 9 mg compound is solved in 1 ml acetone and diluted with acetone to the desired concentration. 250 μl of the test solution is filled in 25 ml glass test tubes and homogeneously distributed on the inner walls by rotation and tilting on a shaking device (2 h at 30 rpm). With a compound concentration of 900 ppm, an inner surface of 44.7 cm.sup.2 and a homogeneous distribution, a dose of 5 μg/cm.sup.2 is achieved.
[0782] After the solvent has evaporated, each test tube is filled with 5-10 adult brown dog ticks (Rhipicephalus sanguineus), closed with a perforated lid and incubated in a lying position at room temperature and relative humidity. After 48 hours efficacy is determined. The ticks are patted on the ground of the tubes and are incubated on a heating plate at 45-50° C. for at most 5 minutes. Immotile or uncoordinated moving ticks, which are not able to escape the heat by climbing upwards, are marked as dead or moribund.
[0783] A compound shows a good efficacy against Rhipicephalus sanguineus, if at a compound concentration of 5 μg/cm.sup.2 an efficacy of at least 80% is monitored. An efficacy of 100% means all ticks are dead or moribund; 0% means no ticks are dead or moribund.
[0784] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-009, I-010, I-012, I-015, I-049, I-052, I-056, I-067.
[0785] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 5 μg/cm.sup.2 (=500 g/ha): I-074.
[0786] Boophilus microplus—Injection Test
[0787] Solvent: dimethyl sulfoxide
[0788] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with solvent to the desired concentration.
[0789] Five adult engorged female ticks (Boophilus microplus) are injected with 1 μl compound solution into the abdomen. The ticks are transferred into replica plates and incubated in a climate chamber.
[0790] After 7 days egg deposition of fertile eggs is monitored. Eggs where fertility is not visible are stored in a climate chamber till hatching after about 42 days. An efficacy of 100% means all eggs are infertile; 0% means all eggs are fertile.
[0791] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 μg/animal: I-003, I-005, I-006, I-007, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-020, I-022, I-024, I-025, I-026, I-027, I-028, I-030, I-031, I-032, I-033, I-034, I-036, I-037, I-039, I-040, I-041, I-042, I-044, I-045, I-046, I-047, I-048, I-049, I-052, I-053, I-055, I-056, I-058, I-061, I-062, I-063, I-066, I-067, I-068, I-069, I-070, I-073, I-074, I-076, I-077, I-078, I-080.
[0792] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 μg/animal: I-017.
[0793] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 20 μg/animal: T-057, T-064.
[0794] Boophilus microplus—Dip Test
[0795] Test animal: cattle ticks (Boophilus microplus) strane Parhurst, SP-resistant
[0796] Solvent: dimethyl sulfoxide
[0797] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with water to the desired concentration.
[0798] This compound solution is pipetted into tubes. 8-10 engorged, adult, female cattle ticks (Boophilus microplus) are placed in perforated tubes. These tubes are immersed in the aqueous compound solution until the ticks are completely moistened. After the liquid has drained off, the ticks are transferred to a filter paper in a plastic tray and stored in a climate chamber.
[0799] After 7 days egg deposition of fertile eggs is monitored. Eggs where fertility is not visible are stored in a climate chamber till hatching after about 42 days. An efficacy of 100% means all eggs are infertile; 0% means all eggs are fertile.
[0800] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 ppm: I-009, I-013, I-019, I-028, I-037, I-041, I-046, I-047, I-049.
[0801] In this test, for example, the following compounds from the preparation examples showed good activity of 95% at an application rate of 100 ppm: I-012.
[0802] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 ppm: I-007, I-042.
[0803] Ctenocephalides felis—Oral Test
[0804] Solvent: dimethyl sulfoxide
[0805] To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent, and the concentrate is diluted with cattle blood to the desired concentration.
[0806] Approximately 20 adult unfed cat fleas (Ctenocephalides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom, are filled with cattle blood supplied with compound solution and placed on the gauze covered top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37° C. whereas the flea chamber is kept at room temperature.
[0807] After 2 days mortality in % is determined. 100% means all the fleas have been killed; 0% means none of the fleas have been killed.
[0808] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 ppm: I-003, I-005, I-006, I-007, I-009, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-020, I-021, I-024, I-025, I-026, I-027, I-028, I-030, I-032, I-033, I-034, I-036, I-037, I-039, I-040, I-041, I-042, I-044, I-046, I-047, I-048, I-049, I-052, I-053, I-056, I-058, I-060, I-061, I-062, I-063, I-067, I-073, I-075, I-077, I-078, I-079, I-080, I-083, I-085, I-086, I-088, I-089, I-090, I-092, I-093, I-094, I-095, I-096, I-097, I-098, I-099, I-100.
[0809] In this test, for example, the following compounds from the preparation examples showed good activity of 95% at an application rate of 100 ppm: I-045.
[0810] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 ppm: I-057, I-076.
[0811] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 ppm: I-070, I-074.
[0812] Diabrotica balteata—Spray Test
[0813] Solvent: 78.0 parts by weight of acetone [0814] 1.5 parts by weight of dimethylformamide
[0815] Emulsifier: alkylarylpolyglycol ether
[0816] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0817] Soaked wheat seeds (Triticum aestivum) are placed in a multiple well plate filled with agar and some water and are incubated for 1 day to germinate (5 seeds per well). The germinated wheat seeds are sprayed with a test solution containing the desired concentration of the active ingredient. Afterwards each unit is infected with 10-20 larvae of the banded cucumber beetle (Diabrotica balteata).
[0818] After 7 days efficacy in % is determined. 100% means all the seedlings have grown up like in the untreated, uninfected control; 0% means none of the seedlings have grown.
[0819] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 160 μg/well (=500 g/ha): I-001, I-003, I-004, I-005, I-006, I-007, I-008, I-011, I-012, I-013, I-014, I-016, I-018, I-019, I-020, I-022, I-024, I-026, I-027, I-028, I-029, I-031, I-032, I-033, I-034, I-036, I-037, I-038, I-039, I-040, I-041, I-042, I-043, I-046, I-047, I-048, I-049, I-052, I-053, I-054, I-056, I-059, I-061, I-062, I-063, I-065, I-066, I-067, I-068, I-069, I-072, I-073, I-074, I-075, I-076, I-077, I-081, I-082, I-083, I-084, I-085, I-088, I-089, I-090, I-092, I-093, I-096, I-097, I-098, I-099, I-100, I-101, I-103, I-104, I-105, I-106, I-107, I-108, I-110, I-112, I-115, I-116.
[0820] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 160 μg/well (=500 g/ha): I-025, I-030, I-044, I-045, I-057, I-078, I-080, I-103, I-113.
[0821] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 80 μg/well (=250 g/ha): I-003, I-005, I-006, I-007, I-008, I-009, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-020, I-022, I-024, I-026, I-027, I-028, I-029, I-030, I-032, I-033, I-034, I-036, I-037, I-038, I-039, I-040, I-041, I-042, I-044, I-045, I-046, I-047, I-048, I-052, I-053, I-054, I-056, I-057, I-061, I-062, I-063, I-065, I-066, I-067, I-068, I-072, I-073, I-074, I-075, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-083, I-084, I-085, I-086, I-088, I-089, I-090, I-092, I-093, I-094, I-096, I-097, I-098, I-099, I-100, I-101, I-102, I-103, I-105, I-106.
[0822] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 80 μg/well (=250 g/ha): I-049, I-060.
[0823] Meloidogyne incognita—Test
[0824] Solvent: 125.0 parts by weight of acetone
[0825] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration.
[0826] Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of the southern root-knot nematode (Meloidogyne incognita) and salad seeds. The salad seeds germinate and the seedlings grow. Galls develop in the roots.
[0827] After 14 days the nematicidal activity is determined on the basis of the percentage of gall formation. 100% means no galls were found and 0% means the number of galls found on the roots of the treated plants was equal to that in untreated control plants.
[0828] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 ppm: I-001, I-010.
[0829] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 ppm: 1-002, I-013.
[0830] Myzus persicae—Oral Test
[0831] Solvent: 100 parts by weight acetone
[0832] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration.
[0833] 50 μl compound solution is filled in microtiter plates and 150 μl IPL41 insect medium (33%+15% sugar) is added to obtain a total volume of 200 μl per well. Afterwards the plates are sealed with parafilm through which a mixed population of the green peach aphid (Myzus persicae) can suck on the compound preparation.
[0834] After 5 days mortality in % is determined. 100% means all aphids have been killed and 0% means none of the aphids have been killed.
[0835] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20 ppm: I-006, I-007, I-008.
[0836] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 20 ppm: I-003.
[0837] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 4 ppm: I-009, I-010, I-014, I-015, I-021, I-024, I-028, I-030, I-033, I-034, I-036, I-038, I-040, I-041, I-042, I-046, I-048, I-049, I-052, I-054, I-056, I-061, I-063, I-067, I-076, I-077, I-078, I-081, I-098, I-100, I-101, I-103, I-105, I-106, I-107, I-115, I-116.
[0838] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 4 ppm: I-007, I-018, I-072, I-089, I-104, I-112.
[0839] Myzus persicae—Spray Test
[0840] Solvent: 78.0 parts by weight acetone [0841] 1.5 parts by weight dimethylformamide
[0842] Emulsifier: alkylarylpolyglycol ether
[0843] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0844] Chinese cabbage (Brassica pekinensis) leaf disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient of the desired concentration.
[0845] After 5 days mortality in % is determined. 100% means all aphids have been killed and 0% means none of the aphids have been killed.
[0846] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-013, I-015, I-033, I-034, I-076, I-110, I-115, I-116.
[0847] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-009, I-014, I-037, I-038, I-054, I-049, I-052, I-056, I-065, I-067, I-073, I-077, I-088, I-089, I-098, I-104, I-105, I-106, I-107.
[0848] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-015, I-021, I-033, I-034, I-049, I-056, I-116.
[0849] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 g/ha: I-013, I-014, I-024, I-030, I-037, I-054, I-067, I-077, I-089, I-098, I-107, I-110, I-115.
[0850] Nezara viridula—Spray Test
[0851] Solvent: 78.0 parts by weight of acetone [0852] 1.5 parts by weight of dimethylformamide
[0853] Emulsifier: alkylarylpolyglycol ether
[0854] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0855] Barley plants (Hordeum vulgare) infested with larvae of the southern green stink bug (Nezara viridula) are sprayed with a test solution containing the desired concentration of the active ingredient.
[0856] After 4 days mortality in % is determined. 100% means all the stink bugs have been killed; 0% means none of the stink bugs have been killed.
[0857] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-005, I-007, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-018, I-028, I-029, I-030, I-033, I-034, I-037, I-041, I-042, I-047, I-048, I-049, I-052, I-054, I-056, I-061, I-062, I-067, I-077, I-078, I-080, I-081, I-082, I-085, I-088, I-089, I-090, I-093, I-094, I-100, I-101, I-102, 1-103, I-105, I-106, I-107, I-112, I-113, I-115, I-116.
[0858] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-008, I-019, I-065, I-079, I-092, I-098, I-104, I-110.
[0859] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-007, I-010, I-012, I-014, I-018, I-023, I-028, I-034, I-037, I-041, I-042, I-048, I-049, I-052, I-056, I-067, I-077, I-080, I-103, I-105, I-107, I-112.
[0860] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 100 g/ha: I-008, I-054, I-078, I-079, I-081, I-088, I-089, I-116.
[0861] Nilaparvata lugens—Spray Test
[0862] Solvent: 78.0 parts by weight of acetone [0863] 1.5 parts by weight of dimethylformamide
[0864] Emulsifier: alkylarylpolyglycol ether
[0865] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0866] Rice plants (Oryza sativa) are sprayed with a preparation of the active ingredient of the desired concentration and the plants are infested with the brown planthopper (Nilaparvata lugens).
[0867] After 14 days mortality in % is determined. 100% means all planthoppers have been killed and 0% means none of the planthoppers have been killed.
[0868] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-012, I-014, I-034, I-037, I-039, I-048, I-049, I-066, I-070, 1-077, I-078, I-080, I-094.
[0869] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-041, I-067.
[0870] In this test, for example, the following compounds from the preparation examples showed good activity of 70% at an application rate of 500 g/ha: I-069.
[0871] Phaedon cochleariae—Spray Test
[0872] Solvent: 78.0 parts by weight of acetone [0873] 1.5 parts by weight of dimethylformamide
[0874] Emulsifier: alkylarylpolyglycol ether
[0875] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0876] Chinese cabbage (Brassica pekinensis) leaf disks are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf disks are infested with mustard beetle larvae (Phaedon cochleariae).
[0877] After 7 days mortality in % is determined. 100% means all beetle larvae have been killed and 0% means none of the beetle larvae have been killed.
[0878] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-003, I-005, I-006, I-007, I-008.
[0879] Spodoptera frugiperda—Spray Test
[0880] Solvent: 78.0 parts by weight acetone [0881] 1.5 parts by weight dimethylformamide
[0882] Emulsifier: alkylarylpolyglycol ether
[0883] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0884] Maize (Zea mays) leaf sections are sprayed with a preparation of the active ingredient of the desired concentration. Once dry, the leaf sections are infested with fall armyworm larvae (Spodoptera frugiperda).
[0885] After 7 days mortality in % is determined. 100% means all caterpillars have been killed and 0% means none of the caterpillars have been killed.
[0886] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 500 g/ha: I-003, I-005, I-006, I-007, I-008, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-020, I-021, I-026, I-027, I-028, I-029, I-030, I-033, I-034, I-036, I-038, I-039, I-040, I-041, I-042, I-045, I-046, I-047, I-048, I-049, I-052, I-052, I-053, I-056, I-060, I-061, I-062, I-065, I-066, I-067, I-068, I-069, I-070, I-072, I-074, I-076, I-077, I-078, I-079, I-080, I-081, I-082, I-083, I-085, I-087, I-088, I-089, I-090, I-092, I-093, I-097, I-098, I-099, I-100, I-101, I-103, 1-104, I-105, I-106, I-107, I-110, I-113, I-115, I-116.
[0887] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 500 g/ha: I-022, I-063, I-086, I-108, I-112.
[0888] In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 100 g/ha: I-007, I-008, I-009, I-010, I-011, I-012, I-013, I-014, I-015, I-016, I-018, I-019, I-026, I-027, I-028, I-029, I-033, I-034, I-036, I-037, I-038, I-039, I-040, I-041, I-042, I-045, I-046, I-047, I-048, I-049, I-052, I-056, I-060, I-061, I-062, I-065, I-066, I-067, I-068, I-070, I-074, I-076, I-077, I-078, I-080, I-081, I-082, I-083, I-085, I-087, I-088, I-089, I-090, I-092, I-098, I-100, I-103, I-104, I-105, I-106, I-107, I-110, I-115, I-116.
[0889] In this test, for example, the following compounds from the preparation examples showed good activity of 83% at an application rate of 100 g/ha: I-030, I-072.
[0890] In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of 100 g/ha: I-113.
[0891] Tetranychus urticae—Spray Test (OP-Resistant)
[0892] Solvent: 78.0 parts by weight acetone [0893] 1.5 parts by weight dimethylformamide
[0894] Emulsifier: alkylarylpolyglycol ether
[0895] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.
[0896] French bean (Phaseolus vulgaris) leaf disks infected with all instars of the two spotted spidermite (Tetranychus urticae), are sprayed with a preparation of the active ingredient of the desired concentration.
[0897] After 6 days mortality in % is determined. 100% means all spider mites have been killed and 0% means none of the spider mites have been killed.
[0898] In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of 500 g/ha: I-003, I-042.
[0899] Aedes aegypti Test (AEDSAE Surface Treatment & Contact Assay)
[0900] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)
[0901] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Aedes aegypti strain MONHEIM are placed onto the dried surface. The exposure time is 30 minutes.
[0902] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.
[0903] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-007, I-009, I-010, I-011, I-013, I-014, I-015, I-018, I-019, I-020, I-026, I-028, I-030, I-033, I-034, I-038, I-041, I-042, I-046, I-047, I-048, I-049, I-052, I-056, I-063.
[0904] The following examples showed in this test efficacy of 90-100% at a surface concentration of 4 mg/m.sup.2: I-007, I-009, I-010, I-011, I-013, I-014, I-015, I-018, I-019, I-028, I-033, I-034, I-038, I-039, I-041, I-042, I-046, I-047, I-048, I-049, I-052, I-056, I-063.
[0905] Culex quinquefasciatus Test (CULXFA Surface Treatment & Contact Assay)
[0906] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)
[0907] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Culex quinquefasciatus strain P00 are placed onto the dried surface. The exposure time is 30 minutes.
[0908] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.
[0909] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-007, I-011, I-013, I-014, I-015, I-018, I-019, I-024, I-026, I-028, I-030, I-033, I-034, I-038, I-041, I-042, I-046, I-047, I-048, I-049, I-052, I-056.
[0910] The following examples showed in this test efficacy of 90-100% at a surface concentration of 4 mg/m.sup.2: I-007, I-009, I-011, I-013, I-014, I-015, I-018, I-019, I-020, I-028, I-033, I-034, I-041, I-042, I-046, I-047, 1-048, I-049, I-052, I-056.
[0911] Anopheles funestus Test (ANPHFU Surface Treatment & Contact Assay)
[0912] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)
[0913] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult mosquitoes of the species Anopheles funestus strain FUMOZ-R (Hunt et al., Med. Vet. Entomol. 2005 September; 19(3): 271-275) are placed onto the dried surface. The exposure time is 30 minutes.
[0914] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.
[0915] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-013, I-014, I-015, I-018, I-019, I-024, I-026, I-028, I-030, I-033, I-038, I-041, I-042, I-046, I-047, I-049.
[0916] The following examples showed in this test efficacy of 85-100% at a surface concentration of 4 mg/m.sup.2: I-013, I-014, I-018, I-019, I-026, I-028, I-034, I-038, I-041, I-042, I-046, I-047, I-048, I-052.
[0917] Musca domestica Test (MUSCDO Surface Treatment & Contact Assay)
[0918] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)
[0919] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult flies of the species Musca domestica strain WHO-N are placed onto the dried surface. The exposure time is 30 minutes.
[0920] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.
[0921] The following examples showed in this test efficacy of 90-100% at a surface concentration of 20 mg/m.sup.2: I-007, I-009, I-010, I-011, I-013, I-014, I-015, I-018, I-019, I-028, I-034, I-041, I-042, I-046, I-047, I-048, 1-049, I-052, I-056.
[0922] The following examples showed in this test efficacy of 90-100% at a surface concentration of 4 mg/m.sup.2: I-007, I-009, I-011, I-014, I-018, I-019, I-028, I-041, I-042, I-046, I-047, I-048, I-049, I-052, I-056.
[0923] Blattella germanica Test (BLTTGE Surface Treatment & Contact Assay)
[0924] Solvent: Aceton+2000 ppm rapeseed oil methyl ester (RME)
[0925] In order to produce a sufficient, active ingredient containing solution it is necessary to solve the test compound in the solvent-mix (acetone at 2 mg/ml/RME 2000 ppm). This solution is pipetted onto a glazed tile and after evaporation of the acetone, adult animals of the species Blattella germanica strain PAULINIA are placed onto the dried surface. The exposure time is 30 minutes.
[0926] Mortality in percent (%) is determined 24 hours after contact of the insects to the treated surface. 100% mortality means that all tested insects are dead, whereas 0% means that no insect died.
[0927] The following examples showed in this test efficacy of 80-100% at a surface concentration of 20 mg/m.sup.2: I-007, I-011.