Claims
- 1. A substituted 1,4-naphthoquinone of the formula ##STR133## in which m represents the number 0 or a number from 1 to 12,
- A.sup.1 represents hydrogen, methyl, benzyl, acetyl, methoxycarbonyl, benzenesulphonyl or toluenesulphonyl and
- 2represents trifluoromethyl, 3-trifluoromethylcyclohexyl, 3-trifluoromethyl-phenyl, 4-trimethylsilyl-cyclohexyl or 4-trifluoromethylthiophenyl, with the proviso that m is other than 0 and 2 if A.sup.2 represents 3-trifluoromethyl-cyclohexyl or 3-trifluoromethyl-phenyl.
- 2. A substituted 1,4-naphthoquinone according to claim 1, wherein
- m represents the number zero or a number from 1 to 10,
- A.sup.1 represents hydrogen, methyl, acetyl or benzyl and
- A.sup.2 represents trifluoromethyl, 3-trifluoromethylcyclohexyl, 3-trifluoromethyl-phenyl, 4-trifluoromethylsilyl-cyclohexyl or 4-trifluoromethylthio-phenyl,
- with the proviso that m is other than zero and 2 if A.sup.2 represents 3-trifluoromethyl-cyclohexyl or 3-trifluoromethyl-phenyl.
Priority Claims (2)
| Number |
Date |
Country |
Kind |
| 3722018 |
Jul 1987 |
DEX |
|
| 3801743 |
Jan 1988 |
DEX |
|
Parent Case Info
This is a division of application Ser. No. 212,816, filed June 29, 1988, now U.S. Pat. No. 4,929,642.
The invention relates to the use of substituted 4-naphthoquinones, some of which are known, as agents for combating pests, in particular as acaricides and fungicides, and to new substituted 1,4-naphthoquinones and processes for their preparation.
It is known that certain substituted 1,4-naphthoquinones, such as, for example, 2-nonyl-, 2-decyl- and 2-(3-cyclohexyl-propyl)-3-hydroxy-1,4-naphthoquinone, have insecticidal and acaricidal properties (compare U.S. Pat. No. 2,572,946).
A fungicidal action of such compounds has also been disclosed (compare Pestic. Sci. 4 (1973), 193-200). However, the action of these compounds is not always satisfactory, especially in the case of low application rates and/or concentrations of active compound.
It is also known that certain substituted 1,4-naphthoquinones which contain specific cycloalkyl groups can be used against Protozoa on stock animals (compare European Patent No. A-2,228, European Patent No. A-77,550, European Patent No. A-77,551, European Patent No. A-123,238 and European Patent No. A-123,239). However, nothing is as yet known of a use of such compounds in plant protection, for example, as acaricides or as fungicides.
It has now been found that the substituted 1,4-naphthoquinones, some of which are known, of the general formula (I) ##STR3## in which
n represents the number zero or a number from 1 to 12,
R.sup.1 represents hydrogen, or represents an optionally substituted radical R from the series comprising alkyl, aralkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl and arylsulphonyl and
R.sup.2 represents halogenoalkyl, optionally substituted aryl or substituted cycloalkyl, have a powerful action as agents for combating pests, in particular as acaricides and as fungicides.
Surprisingly, the substituted 1,4-naphthoquinones of the general formula (I) exhibit a more powerful acaricidal and fungicidal action than the abovementioned known compounds of similar structure.
The invention preferably relates to the use of agents for combating pests and pest-combating agents, in particular acaricides and fungicides, based on compounds of the general formula (I), in which
n represents the number zero, 1 or 2,
R.sup.1 represents hydrogen, or represents a radical R which is optionally substituted as described below and is chosen from the series comprising C.sub.1 -C.sub.12 -alkyl (which is optionally substituted by fluorine, chlorine or C.sub.3 -C.sub.6 -cycloalkyl), benzyl (which is optionally substituted by fluorine, chlorine or bromine), C.sub.1 -C.sub.12 -alkylcarbonyl (which is optionally substituted by fluorine, chloride, bromine, phenyl, C.sub.1 -C.sub.2 -alkoxy or C.sub.3 -C.sub.6 -cycloalkyl), C.sub.1 -C.sub.4 -alkoxy-carbonyl, (C.sub.1 -C.sub.8 -alkylsulphonyl (which is optionally substituted by fluorine or chlorine) and phenylsulphonyl and naphthylsulphonyl (which are optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylsulphonyl, dimethylaminosulphonyl and/or C.sub.1 -C.sub.4 -alkoxycarbonyl), and
R.sup.2 represents C.sub.1 -C.sub.8 -alkyl, which is substituted by fluorine and/or chlorine, phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C.sub.1 -C.sub.6 -alkyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.2 -fluoroalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.2 -fluoroalkylthio, C.sub.1 -C.sub.4 -alkylsulphinyl, C.sub.1 -C.sub.2 -fluoroalkylsulphinyl, C.sub.1 -C.sub.4 -alkylsulphonyl, C.sub.1 -C.sub.2 -fluoroalkylsulphonyl and/or tri-(C.sub.1 -C.sub.2 -alkyl)-silyl or cyclohexyl which is substituted by C.sub.1 -C.sub.6 -alkyl, trifluoromethyl and/or tri(C.sub.1 -C.sub.2 -alkyl)-silyl.
Compounds of the formula (I) which are particularly preferably used according to the invention are those in which
n represents the numbers zero, 1 or 2,
R.sup.1 represents hydrogen, methyl or acetyl and R.sup.2 represents phenyl which is substituted by fluorine, chlorine, C.sub.1 -C.sub.4 -alkyl, trifluoromethyl, C.sub.1 -C.sub.3 -alkoxy, trifluoromethoxy, C.sub.1 -C.sub.3 -alkylthio, trifluoromethylsulphenyl, C.sub.1 -C.sub.3 -alkylsulphinyl, trifluoromethylsulphinyl, C.sub.1 -C.sub.3 -alkylsulphonyl, trifluoromethylsulphonyl or trimethylsilyl, or cyclohexyl which is substituted by C.sub.1 -C.sub.4 -alkyl, trifluoromethyl or trimethylsilyl.
Examples which may be mentioned of the compounds of the formula (I) to be used according to the invention are: 2-(4-tert.-butyl-cyclohexyl)-3-hydroxy-1,4-naphthoquinone, 2-(4-trimethylsilyl-cyclohexyl)-3-hydroxy-1,4-naphthoquinone, 2-(3-trifluoromethyl-1-cyclohexyl-methyl)-3-hydroxy-1,4-naphthoquinone, 2-(4-trifluoromethyl-1-cyclohexyl-methyl)-3-hydroxy-1,4-naphthoquinone, 2-(2-(4-trifluoromethyl-1-cyclohexyl)-ethyl)-3-hydroxy-1,4-naphthoquinone, 2-(3-trifluoromethyl-1-cyclohexyl-methyl)-3-acetoxy-1,4-naphthoquinone, 2-(3-trifluoromethyl-phenyl-methyl)-3-hydroxy-1,4-naphthoquinone and 2-(2-(4-trifluoromethylthio-phenyl)-ethyl)-3-hydroxy-1,4-naphthoquinone.
These compounds are especially preferred because of their outstanding acaricidal and fungicidal action.
US Referenced Citations (7)
Foreign Referenced Citations (3)
| Number |
Date |
Country |
| 0123238 |
Oct 1984 |
EPX |
| 7107128 |
Dec 1971 |
FRX |
| 0273947 |
Nov 1987 |
JPX |
Non-Patent Literature Citations (6)
| Entry |
| Pestic. Sci. 4, (1973), pp. 193-200. |
| Liebigs Ann. Chem. 763, (1972), pp. 135-147. |
| J. Am. Che. Soc. 58, (1936), pp. 1163-1167. |
| ibid. 70 (1948), pp. 3165-3174 and ibid: 70 (1948) pp. 3174-3175. |
| ibid. 74 (1952), pp. 3910-3915. |
| J. Chem. Soc. 1935, pp. 1850-1854. |
Divisions (1)
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Number |
Date |
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| Parent |
212816 |
Jun 1988 |
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Patent Grant
4970328
