Claims
- 1. A compound represented by the general formula, ##STR25## R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a lower alkyl group, a trifluoromethyl group, a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group, or are, taken together, a methylenedioxy group; R.sub.3 is a vinyl group or a ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group; R.sub.5 is a hydrogen atom or a fluorine atom; R.sub.6 is a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or a trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom; and when Z is a group of the formula --CH.dbd., Y is an oxygen atom, a sulfur atom, a methylene group or a group represented by the formula --NH--.
- 2. The compound according to claim 1, wherein R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom, a C.sub.1-4 alkyl group, a trifluoromethyl group, a C.sub.1-4 alkoxyl group, a C.sub.2-4 alkenyloxy group or a halogenated C.sub.1-4 alkoxyl group, or are, taken together, a methylenedioxy group; R.sub.4 is a C.sub.1-4 alkyl group; R.sub.6 is a hydrogen atom, a halogen atom, a C.sub.1-4 lower alkyl group, a C.sub.1-4 alkoxyl group or a trifluoromethyl group; Z is a group represented by the formula --CH.dbd.; and Y is an oxygen atom or a group represented by the formula --NH--.
- 3. The compound according to claim 2, wherein R.sub.4 is a methyl group.
- 4. The compound according to claim 2, wherein R.sub.3 is an ethynyl group and R4 is a methyl group.
- 5. The compound according to claim 4, wherein R.sub.I is a halogen atom, a C.sub.2- alkyl group, a trifluoromethyl group, a C.sub.2-4 alkoxyl group, a C.sub.2-4 alkenyloxy group or a fluorinated C.sub.1-4 alkoxyl group; R2 is a hydrogen atom; R5 is a fluorine atom; R6 is a hydrogen atom or a halogen atom; and Y is a group represented by the formula --NH--.
- 6. The compound according to claim 4, wherein R.sub. is a halogen atom, a C.sub.2-4 alkyl group, a trifluoromethyl group a C.sub.2-4 alkoxyl group, a C .sub.2-4 alklenyloxy group or a fluorinated C.sub.2-4 alkoxyl group; R .sub.2 is a hydrogen group; R.sub.6 is a hydrogen atom or a halogen atom; and Y is an oxygen atom.
- 7. A compound of the formula ##STR26##
- 8. A compound of the formula, ##STR27##
- 9. A compound of the formula, ##STR28##
- 10. A compound of the formula, ##STR29##
- 11. A compound of the formula, ##STR30##
- 12. A compound of the formula, ##STR31##
- 13. A compound of the formula, ##STR32##
- 14. A compound of the formula, ##STR33##
- 15. A compound of the formula, ##STR34##
- 16. A compound of the formula, ##STR35##
- 17. A compound of the formula, ##STR36##
- 18. A compound of the formula, ##STR37##
- 19. A compound of the formula, ##STR38##
- 20. A compound of the formula, ##STR39##
- 21. A compound of the formula, ##STR40##
- 22. An insecticidal and acaricidal composition which comprises as an active ingredient an insecticidally and/or an acaricidally effective amount of the compound as recited in claim 1 and an inert carrier.
- 23. An insecticidal and acaricidal composition which comprises as an active ingredient an insecticidally and/or an acaricidally effective amount of the compound as recited in claim 3 and an inert carrier.
- 24. An insecticidal and acaricidal composition which comprises as an active ingredient an insecticidally and/or an acaricidally effective amount of the compound as recited in claim 4 and an inert carrier.
- 25. An insecticidal and acaricidal composition which comprises as an active ingredient an insecticidally and/or acaricidally effective amount of the compound as recited in claim 5 and an inert carrier.
- 26. An insecticidal and acaricidal composition which comprises as an active ingredient an insecticidally and/or an acaricidally effective amount of the compound as recited in claim 6 and an inert carrier.
- 27. A method for controlling an insect and/or an acarid which comprises applying to said insect and/or acarid an insecticidally and/or acaricidally effective amount of the compound according to claim 1.
Parent Case Info
The present invention relates to a novel compound, its production and an insecticidal and acaricidal composition containing it as an active ingredient.
The present inventors extensively studied to develop a compound having excellent insecticidal and acaricidal activities, and as a result, found that a novel compound represented by the following general formula (I) (hereinafter referred to as present compound) is superior in the insecticidal and acaricidal activities as well as very low in toxicity to fishes. The present inventors thus attained to the present invention. ##STR2## In this formula, R1.sub.1 and R.sub.2, which may be the same or different, are a hydrogen atom, a halogen atom (e.g. fluorine, chlorine, bromine), a lower alkyl group (e.g. C.sub.1 -C.sub.5 alkyl), a trifluoromethyl group, a lower alkoxyl group (e.g. C.sub.1 -C.sub.5 alkoxy), a lower alkenyloxy group (e.g. C.sub.2 -C.sub.5 alkenyloxy) or a halogenated lower alkoxyl group (e.g. fluOrinated or chlorinated C.sub.1 -C.sub.5 alkoxy), or, taken together, a methylenedioxy group; R.sub.3 is a vinyl or ethynyl group; R.sub.4 is a hydrogen atom or a lower alkyl group (e.g. C.sub.1 -C.sub.5 alkyl); R.sub.5 is a hydrogen or fluorine atom; R.sub.6 is a hydrogen atom or a halogen atom (e.g. fluorine, chlorine, bromine), a lower alkyl group (e.g. C.sub.1 -C.sub.5 alkyl), a lower alkoxyl group (e.g. C.sub.1 -C.sub.5 alkoxy) or trifluoromethyl group; Z is a nitrogen atom or a group represented by the formula --CH.dbd.; when Z is a nitrogen atom, Y is an oxygen atom, and when Z is a group of the formula --CH.dbd., Y is an oxygen or sulfur atom, a methylene group or a group represented by the formula --NH--.
Of the present compounds represented by the foregoing general formula (I), preferred compounds are such that R.sub.1 and R.sub.2, which may be the same or different, are a hydrogen or halogen atom, or a C.sub.1 -C.sub.4 alkyl, trifluoromethyl, C.sub.1 -C.sub.4 alkoxyl, C.sub.2 -C.sub.4 alkenyloxy or halogenated C.sub.1 -C.sub.4 alkoxyl group, or, taken tOgether, a methylenedioxy group; R.sub.4 is a C.sub.1 -C.sub.4 alkyl group; R.sub.6 is a hydrogen or halogen atom, or a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxyl or trifluoromethyl group; Z is a group represented by the formula --CH.dbd.; and Y is an oxygen atom or a group represented by the formula --NH--. More preferred compounds are such that, in the foregoing preferred compounds, R.sub.3 is an ethynyl group and R.sub.4 is a methyl group.
Specific examples of insect pests to which the present compounds are particularly effective include Hemiptera such as planthoppers, leafhoppers, aphids, bugs, whiteflies, etc., Lepidoptera such as diamond-back moth (Plutella xylostella), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), armyworms and cutworms, etc., Diptera such as common mosquito (Culex pipiens pallens), housefly (Musca domestica), etc., Dictyoptera such as German cockroach (Blattella qermanica), etc., Coleoptera, Orthoptera and mites such as carmine spider mite (Tetranychus cinnabarinus), citrus red mite (Panonychus citri), etc. The term "an insecticidal and acaricidal composition" referred to hereinafter includes any composition which comprises the present compound as an active ingredient and is capable of controlling and/or killing insects and/or mites as mentioned above.
The present compounds can be produced, for example, by the following methods.
Method 1:
The present compound represented by the general formula (VI) which corresponds to the present compound of the general formula (I) wherein R.sub.3 is a vinyl group, ##STR3## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6 and Y have the same meanings as described above, can be obtained
(1) by reacting a compound represented by the general formula (II), ##STR4## wherein R.sub.1, R.sub.2 and R.sub.4 have the same meanings as described above, with a compound represented by the general formula (III), ##STR5## wherein R.sub.5, R.sub.6 and Y have the same meanings as described above, and X represents a halogen atom or a tosyloxy or mesyloxy group, for example, in dimethylformamide in the presence of sodium hydride to obtain a nitrile compound represented by the general formula (IV), ##STR6## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6 and Y have the same meanings as described above,
(2) reacting said nitrile compound with a reducing agent (e.g. diisobutylaluminum hydride) to obtain an aldehyde compound represented by the general formula (V), ##STR7## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6 and Y have the same meanings as described above,
(3) and then reacting said aldehyde compound with an ylide compound represented by the formula, ##STR8## according to the Wittig, reaction (refer to Org. Reaction, Vol. 14, pp. 2570-490) to introduce a vinyl group.
Also, the present compound represented by the general formula (VII), which corresponds to the present compound of the general formula (I) wherein R.sub.3 is an ethynyl group, can be obtained by reacting said aldehyde compound (V) with a Wittig reagent for introduction of a dihalomethylene group prepared from, for example, carbon tetrabromide or carbon tetrachloride and triphenyl phosphine, trialkyl phosphine or hexamethylphosphoroustriamide, according to the Wittig reaction (refer to Org. Reaction, Vol. 14, pp. 270-490) to introduce a dihalovinyl group, and then treating the resulting compound with a base. This reaction is expressed as follows: ##STR9## wherein R.sub.1, R.sub.2, R.sub.4, R.sub.5, R.sub.6 and Y have the same meanings as described above, and Q is a bromine or chlorine atom.
Method 2:
First, a nitrile compound represented by the general formula (XV), ##STR10## wherein R.sub.1, R.sub.2, R.sub.5 and R.sub.6 have the same meanings as described above, and R'.sub.4 represents a lower alkyl group, is produced,
(1) by reacting a compound represented by the general formula (VIII), ##STR11## wherein R.sub.5 and R.sub.6 have the same meanings as described above, and R7 represents a lower alkoxyl group, with a compound represented by the general formula (IX), ##STR12## wherein R.sub.1 and R.sub.2 have the same meanings as described above, for example, in tetrahydrofuran in the presence of sodium hydride to obtain a compound represented by the general formula (X), ##STR13## wherein R.sub.1, R.sub.2, R.sub.5 and R.sub.6 have the same meanings as described above,
(2) reacting said compound (X) with a reducing agent (e.g. sodium borohydride), for example, in ethanol to obtain an alcohol compound represented by the general formula (XI), ##STR14## wherein R.sub.1, R.sub.2, R.sub.5, and R.sub.6 have the same meanings as described above,
(3) reacting said alcohol compound (XI) with methanesulfonyl chloride in the presence of a base [e.g. 1,8-diazabicyclo[5,4,0]undec-7-ene(DBU)]or subjecting said alcohol compound (XI) to a reaction with other reagent for dehydration to obtain a compound represented by the general formula (XII), ##STR15## wherein R.sub.1, R.sub.2, R.sub.5 and R.sub.6 have the same meanings as described above,
(4) reducing said compound (XII) with hydrogen gas, for example, in the presence of a noble metal catalyst (e.g. palladium-carbon powder), that is, subjecting said compound (XII) to catalytic hydrogenation, to obtain a compound represented by the general formula (XIII), ##STR16## wherein R.sub.1, R.sub.2, R.sub.5 and R.sub.6 have the same meaning as described above,
(5) and then reacting said compound (XIII) with a compound represented by the general formula (XIV),
Method 3:
The present compound of the general formula (I) wherein R.sub.3 is an ethynyl group, and, at least one of R.sub.1 and R.sub.2 is a lower alkoxyl group, a lower alkenyloxy group or a halogenated lower alkoxyl group can be obtained.
(1) by reacting the dihalovinyl intermediate in the procedures described in Methods 1 and 2, which is represented by the general formula ##STR18## wherein at least one of R.sub.1 and R.sub.2 is a methoxy group, with a reagent for removing the methoxy group to lead to the corresponding hydroxyl compound (compound wherein at least one of R.sub.1 and R.sub.2 is a hydroxyl group),
(2) reacting said hydroxyl compound with a base to convert the dihalovinyl group in the compound into ethynyl group,
(3) and then reacting the resulting compound with a halide represented by the general formula
Examples of the present compounds which can be produced by the foregoing methods will be shown below.
Examples of the compounds thus obtained are shown in Table 1, but the present compounds are not limited to these examples.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
| 4562213 |
Nishida et al. |
Dec 1985 |
|
Foreign Referenced Citations (3)
| Number |
Date |
Country |
| 3326180 |
Jan 1984 |
DEX |
| 42339 |
Mar 1985 |
JPX |
| 2120664 |
Dec 1983 |
GBX |
Patent Grant
4772633
