Claims
- 1. A cyano compound of the formula ##STR203## wherein Z is thiazolyl substituted by halogen, C.sub.1-2 -alkyl, or CF.sub.3
- R.sup.1 is hydrogen, cyano or C.sub.1-4 alkyl,
- m is 0 or 1,
- R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.3-4 alkenyl unsubstituted or substituted by halogen, C.sub.3-4 alkynyl, C.sub.3-8 cycloalkyl unsubstituted or substituted by methyl, unsubstituted phenyl or phenyl substituted by halogen, unsubstituted benzyl or benzyl substituted by halogen, hydroxy, C.sub.1-4 alkoxy or --CH.sub.2 --Z, in which Z is as defined above,
- R.sup.3 is --O--R.sup.4, --S--R.sup.4 or ##STR204## in which R.sup.4 is C.sub.1-6 alkyl, C.sub.3-4 alkenyl, C.sub.3-4 alkynyl, C.sub.3-8 cycloalkyl, unsubstituted phenyl or phenyl substituted by halogen, unsubstituted benzyl or benzyl substituted by halogen, or --(CH.sub.2).sub.n --Z, in which n is 1 or 2 and
- Z has the same meaning as stated above, and
- R.sup.5 and R.sup.6 are hydrogen, C.sub.1-9 alkyl unsubstituted or substituted by at least one substituent selected one substituent selected from the group consisting of halogen, hydroxy, mercapto, C.sub.1-2 alkoxy, C.sub.1-2 alkylthio, C.sub.3-6 cycloalkyl, amino, C.sub.1-2 monoalkylamino, C.sub.2-4 (in total) di-alkylamino, carboxy, C.sub.1-2 alkoxy-carbonyl and cyano, unsubstituted C.sub.3-4 alkenyl or C.sub.3-4 alkenyl substituted by halogen, C.sub.3-4 alkynyl, unsubstituted phenyl or phenyl substituted by halogen, unsubstituted benzyl or benzyl substituted by halogen, C.sub.1-4 alkoxy, hydroxy, formyl, C.sub.1-4 alkoxycarbonyl, C.sub.1-4 alkylamino, C.sub.2-4 (in total)di-alkylamino, amino or ##STR205## in which R.sup.1, Z and m have the same meanings as stated above, and in addition,
- R.sup.5 and R.sup.6 may form, together with the N atom to which they are bonded, a pyrrolidino, piperidino, morpholino, piperazino or isoxazolidino ring which is unsubstituted or substituted by C.sub.1-2 alkyl.
- 2. A cyano compound of the formula (I) according to claim 1, wherein
- R.sup.1 is hydrogen or C.sub.1-3 alkyl,
- m is 0 or 1
- R.sup.2 is hydrogen, C.sub.1-4 alkyl, allyl, propargyl, phenyl unsubstituted or substituted by halogen, benzyl unsubstituted or substituted by halogen, hydroxy, or C.sub.1-3 alkoxy,
- R.sup.3 is --O--R.sup.4, --S--R.sup.4 or ##STR206## in which R.sup.4 is C.sub.1-4 alkyl, allyl, propargyl, C.sub.3-6 cycloalkyl, phenyl unsubstituted or substituted by halogen, or benzyl unsubstituted or substituted by halogen,
- R.sup.5 and R.sup.6 are hydrogen, C.sub.1-9 alkyl unsubstituted or substituted by fluorine or chlorine, allyl unsubstituted or substituted by chlorine, propargyl, phenyl unsubstituted or substituted by chlorine, benzyl unsubstituted or substituted by chlorine, C.sub.1-3 alkoxy, hydroxy, hydroxy-C.sub.1-2 alkyl, mercapto-C.sub.1-2 alkyl, amino-C.sub.1-2 alkyl, C.sub.1-3 alkylamino, dimethylamino, amino, cyano-C.sub.1-2 alkyl, or --CH.sub.2 --Z.sup.2 in which Z.sup.2 is 5-thiazolyl unsubstituted or substituted by halogen, and in addition,
- R.sup.5 and R.sup.6 may form, together with the N-atom to which they are bonded, a pyrrolidino, piperidino, morpholino, piperazino or isoxazolidino ring which is unsubstituted or substituted by methyl.
- 3. A cyano compound of the formula (I) according to claim 1, wherein
- R.sup.1 is hydrogen, methyl, ethyl or propyl,
- m is 0 or 1
- R.sub.2 is hydrogen, methyl, ethyl, propyl, allyl, propargyl, phenyl unsubstituted or substituted by chlorine, hydroxy, methoxy, or ethoxy,
- R.sup.3 is --O--R.sup.4, --S--R.sup.4 or ##STR207## in which R.sup.4 is C.sub.1-3 alkyl, allyl, propargyl cyclohexyl, phenyl, or benzyl unsubstituted or substituted by chlorine,
- R.sup.5 and R.sup.6 are hydrogen, C.sub.1-4 alkyl unsubstituted or substituted by fluorine or chlorine, allyl unsubstituted or substituted by chlorine, propargyl, phenyl unsubstituted or substituted by chlorine, benzyl unsubstituted or substituted by chlorine, methoxy, hydroxy, hydroxyethyl, C.sub.1-2 alkylamino, dimethylamino, amino, cyanoethyl, or 2-chloro-5-thiazolymethyl, and in addition,
- R.sup.5 and R.sup.6 may form, together with the N-atom to which they are bonded, pyrrolidino, piperidino, 2-methylpiperidino, morpholino, piperazino or isoxazolidino.
- 4. A compound according to claim 1, wherein such compound is
- S-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-cyanoisothioura of the following formula: ##STR208## or S-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-cyanoisothiourea of the following formula: ##STR209##
- 5. An insecticidal composition comprising an insecticidally effective amount of a cyano compound according to claim 1 in admixture with a diluent.
- 6. A method of combating insects which comprises applying to insects or to a habitat of insects an insecticidally effective amount of a cyano compound according to claim 1.
- 7. A method according to claim 6, wherein said cyano compound is
- S-methyl-N-(2-chloro-5-thiazolylmethyl)-N'-cyanoisothiourea.
- 8. A compound according to claim 1, which has the formula: ##STR210##
- 9. The method according to claim 6, wherein said cyano compound has the formula: ##STR211##
Priority Claims (2)
Number |
Date |
Country |
Kind |
63-264020 |
Oct 1988 |
JPX |
|
64-057813 |
Mar 1989 |
JPX |
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Parent Case Info
This application is a continuation of application Ser. No. 678,382, filed Apr. 1, 1991 now abandoned, which is a division, of application Ser. No. 584,398 now U.S. Pat. No. 5,066,808, filed Sep. 14, 1990 which is a continuation application of Ser. No. 419,428, filed Oct. 10, 1989 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5063236 |
Gsell |
Nov 1991 |
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Foreign Referenced Citations (1)
Number |
Date |
Country |
0235725 |
Feb 1987 |
EPX |
Divisions (1)
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Number |
Date |
Country |
Parent |
584398 |
Sep 1990 |
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Continuations (2)
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Number |
Date |
Country |
Parent |
678382 |
Apr 1991 |
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Parent |
419428 |
Oct 1989 |
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