Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Patent
1984-12-07
1985-12-24
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
549220, 549462, A01N 5716, A01N 5724, C07F 914, C07F 918
Patent
active
045606820
DESCRIPTION:
BRIEF SUMMARY
FIELD OF TECHNOLOGY
The present invention relates to a novel organophosphoric acid ester, a process for its production and a pesticidal composition containing the organophosphoric acid ester.
BACKGROUND OF TECHNOLOGY
Various organic phosphates having pesticidal activities are known. For instance, U.S. Pat. No. 3,839,511 discloses O-ethyl-S-n-propyl-O-(substituted-phenyl)phosphorothiolates represented by the following formula and their pesticidal activities: ##STR2## where X is halogen, lower alkyl, nitro, cyano, lower alkylmercapto, lower alkylsulfinyl or lower alkoxycarbonyl, and m is 1 to 3.
However, a phosphate or thiophosphate of benzofuranol has not been known.
On the other hand, in recent years, it has become difficult to control pests by conventional pesticides because the pests have acquired resistance through the extensive use of the pesticides for many years. Under these circumstances, it is desired to develop a new pesticide having a high pesticidal activity and a low phytotoxicity.
SUMMARY OF THE INVENTION
The present invention provides a novel organophosphoric acid ester represented by the following general formula I, a process for its production and a pesticidal composition containing it as an active ingredient: ##STR3## where R.sup.1 is an alkyl group, R.sup.2 is an alkyl group or a thioalkyl group, each of R.sup.3, R.sup.4 and R.sup.5 is a hydrogen atom, a halogen atom, an alkylthio group, a nitro group, a cyano group, an alkyl group, an alkylsulfinyl group, an alkylsulfonyl group or a trifluoromethyl group, and X is an oxygen atom or a sulfur atom.
In the general formula I, R.sup.1 is preferably a C.sub.1 -C.sub.4 alkyl group, more preferably an ethyl group. When X is an oxygen atom, R.sup.2 is preferably a C.sub.1 -C.sub.4 alkylthio group, more preferably a propylthio group. When X is a sulfur atom, R.sup.2 is preferably a C.sub.1 -C.sub.4 alkyl group or a C.sub.1 -C.sub.4 alkylthio group, more preferably a C.sub.1 -C.sub.3 alkyl group. R.sup.3, R.sup.4 and R.sup.5 may be the same or different and represent a hydrogen atom; a halogen atom, preferably a chlorine atom; a C.sub.1 -C.sub.3 alkylthio group, preferably a methylthio group; a nitro group; a cyano group; a C.sub.1 -C.sub.3 alkyl group, preferably a methyl group; a C.sub.1 -C.sub.3 alkylsulfinyl group, preferably a methylsulfinyl group; a C.sub.1 -C.sub.3 alkylsulfonyl group, preferably a methylsulfonyl group; or a trifluoromethyl group. It is particularly preferred that at least one of R.sup.3, R.sup.4 and R.sup.5, particularly at least one of R.sup.4 and R.sup.5 is a nitro group, a halogen atom, an alkylthio group or a trifluoromethyl group.
The compounds of the present invention have pesticidal activities. As preferred compounds from the view point of the pesticidal activities, the compounds listed in Table 1 may be mentioned. As particularly preferred compounds, there may be mentioned, for instance, O-ethyl-S-n-propyl-O-(2,3-dihydro-b 2,2-dimethyl-4-chloro-7-benzofuranyl)-thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-5-chloro-7-benzofuranyl)thi ophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-4,5-dichloro-7-benzofuranyl )thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-4-methylthio-7-benzofuranyl )thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-5-methylthio-7-benzofuranyl )thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-4-trifluoromethyl-7-benzofu ranyl)thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-4,5,6-trichloro-7-benzofura nyl)thiophosphate, O-ethyl-S-n-propyl-O-(2,3-dihydro-2,2-dimethyl-5-chloro-4-methylthio-7-ben zofuranyl)thiophosphate, and O-ethyl-O-(2,3-dihydro-2,2-dimethyl-4-methylthio-7-benzofuranyl)ethylthion ophosphonate.
The organophosphoric acid ester represented by the general formula I may be obtained by reacting a phosphoric acid ester halide represented by the formula II: ##STR4## where R.sup.1, R.sup.2 and X are as defined above, and Hal is a halogen atom, with a phenol represented by the formula III: ##STR5## where R.su
REFERENCES:
patent: 3590052 (1971-06-01), Barker
patent: 4303653 (1981-12-01), Chiyomaru et al.
Kumiai Chemical, Chemical Abstracts, vol. 98, (1983), 34, 760m.
Hiroki Ohta
Jun Kato
Masatsugu Oda
Mitsubishi Chemical Industries Ltd.
Raymond Richard L.
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