Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-12-22
2000-05-16
O'Sullivan, Peter
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514341, 514342, 514357, 5462707, 5462747, 546331, A01N 4340
Patent
active
060637986
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to new substituted N-methylenethioureas, to a process for their preparation, and to their use in pesticides, in particular as insecticides.
The prior art describes N-substituted amidino(thio)ureas and their use as pharmaceuticals, which differ from the N-methylenethioureas of the present application by the presence of a (thio)carbonyl group in the molecule (BE 894 172; U.S. Pat. No. 4,701,457).
Moreover, JP 53 108 970 describes guanidine derivatives which can also be employed in pharmacology for regulating the secretion of gastric acids. An insecticidal action of the compounds is not known from the most relevant prior art.
There have now been found the new substituted N-methylenethioureas of the general formula (I) ##STR2## in which n represents 0, 1 or 2, 3 or 4 nitrogen atoms and/or one or two oxygen or sulphur atoms as hetero atom ring members--the number of ring hetero atoms being 1, 2, 3 or 4--and which is optionally substituted by halogen, cyano, nitro, alkyl, halogenoalkyl, alkenyl, halogenoalkenyl, alkinyl, alkoxy, halogenoalkoxy, alkenyloxy, halogenoalkenyloxy, alkinyloxy, alkylthio, halogenoalkylthio, alkenylthio, halogenoalkenylthio, alkinylthio, alkylsulphinyl, halogeno-alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, amino, alkylamino, dialkylamino, aryl, aryloxy, arylthio, arylamino, aralkyl, formylamino, alkylcarbonylamino, formyl, carbamoyl, alkylcarbonyl and/or alkoxy-carbonyl, SR.sup.5 or OR.sup.5, substituted ethylene or propylene bridge which can optionally be interrupted by 1 further hetero atom.
Furthermore, it has been found that the new substituted N-methylenethioureas of the general formula (I) are obtained when the corresponding N'-aralkyl-N-cyano-amidine of the general formula (II) ##STR3## in which Het, n, R.sup.1 and R.sup.2 have the abovementioned meaning diluent and if appropriate with the exclusion of moisture.
Surprisingly, the new substituted N-methylenethioureas of the general formula (I) are distinguished in a surprising manner by a potent insecticidal activity.
The invention preferably relates to compounds of the formula (I) in which consisting of furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3- or 1,2,4-triazolyl, oxazolyl, isoxazolyl, 1,2,4- or 1,3,4-oxadiazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1,2,4-, 1,2,5- or 1,3,4-thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl and pyrazinyl, which is optionally substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, C.sub.1 -C.sub.4 -alkyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.4 -alkenyl (which is optionally substituted by fluorine and/or chlorine), C.sub.2 -C.sub.4 -alkinyl, C.sub.1 -C.sub.4 -alkoxy (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkenyloxy (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkinyloxy, C.sub.1 -C.sub.4 -alkylthio (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkenylthio (which is optionally substituted by fluorine and/or chlorine), C.sub.3 -C.sub.4 -alkinylthio, C.sub.1 -C.sub.4 -alkylsulphinyl (which is optionally substituted by fluorine and/or chlorine), C.sub.1 -C.sub.4 -alkylsulphonyl (which is optionally substituted by fluorine and/or chlorine), amino, C.sub.1 -C.sub.4 -alkylamino, di-(C.sub.1 -C.sub.4 -alkyl)-amino, phenyl, phenoxy, phenylthio, phenylamino, benzyl, formylamino, C.sub.1 -C.sub.4 -alkyl, carbonylamino, formyl, carbamoyl, C.sub.1 -C.sub.4 -alkyl-carbonyl and/or C.sub.1 -C.sub.4 -alkoxy-carbonyl, and NR.sup.3 R.sup.4, SR.sup.5 or OR.sup.5, substituted ethylene or propylene bridge which can optionally be interrupted by 1 further oxygen, nitrogen or sulphur atom and optionally substituted by the following substituents: -C.sub.4 -alkoxy, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkinyl.
The invention particularly relates to compounds of the formula (I) in which consisting of pyrazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrazinyl
REFERENCES:
patent: 5063236 (1991-11-01), Gsell
Erdelen Christoph
Findeisen Kurt
Kanellakopulos Johannes
Linker Karl-Heinz
Mencke Norbert
Bayer Aktiengesellschaft
Gil Joseph C.
O'Sullivan Peter
Whalen Lyndanne M.
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