Claims
- 1. A method of combating white fly or Lepidoptera pests at a locus, which comprises treating the locus with a compound of formula (I) ##STR18## or a salt thereof, in which n represents an integer from 0 to 4; m represents an integer 0 or 1;
- each R independently represents a halogen atom or a nitro, cyano, hydroxyl, alkyl, alkenyl, haloalkyl, haloalkenyl, alkoxy, haloalkoxy, haloalkenoxy, amino, alkylamino, dialkylamino, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylamido, cycloalkyl, aryl or aralkyl group; R.sup.1 and R.sup.2 each independently represent an optionally substituted alkoxy group or together represent a group .dbd.O, .dbd.S or .dbd.N--OR.sup.9, where R.sup.9 a hydrogen atom or an optionally substituted alkyl group;
- R.sup.3 represents a hydroxyl group, or a group --OL where L is a leaving group, or a group which in vivo is transformed into a group --OL.sup.1 is a leaving group;
- R.sup.7 and R.sup.8 independently represent an optionally substituted alkoxy group or together represent a group .dbd.O, .dbd.S or .dbd.N--OR.sup.9, where R.sup.9 is as previously defined;
- wherein R.sub.4 and R.sub.5 independently represent a hydrogen or halogen atom or an optionally substituted alkyl or alkenyl group, or together with the interjacent carbon atom represent an optionally substituted C.sub.4-8 cycloalkyl or cycloalkenyl ring; and A represents a straight or branched chain alkyl or alkenyl group, which may be optionally substituted, an acyclic carbon chain of which links the 3 position of the naphthalene ring shown and the moiety --CHR.sup.4 R.sup.5 and wherein A does not include a quaternary carbon atom in that chain; and
- wherein the total number of carbon atoms in the longest carbon chain running from the 3-position of the naphthalene ring shown is no more than 8.
- 2. A method as claimed in claim 1, wherein the pest is Bemisia whitefly.
- 3. A method as claimed in claim 2, wherein the pest is Bemisia tabaci.
- 4. A method as claimed in claim 1, wherein the pest is Spodoptera.
- 5. A method as claimed in claim 1, wherein the locus comprises the pest per se or environments subject to or subjected to attack by the pests.
- 6. A method as claimed in claim 1, wherein R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 each independently represent a C.sub.1-4 alkoxy group or R.sup.1 with R.sup.2 and/or R.sup.7 with R.sup.8 together represent a group .dbd.O.
- 7. A method as claimed in claim 1, wherein R.sup.3 is a group --OL where L is a leaving group, or a group which in vivo is transformed into a group --OL.sup.1, wherein the pK.sub.a value of the acid LOH or L.sup.1 OH in water is from 1 to 7.
- 8. A method as claimed in claim 6, wherein R.sup.3 is a group which in vivo is transformed into a group --OL.sup.1 where L.sup.1 is a leaving group and the transformation is carried out in a pest to be combated.
- 9. A method as claimed in claim 1, wherein the compound of formula (I) is a naphthalene-1,4-dione.
- 10. A method as claimed in claim 1, wherein R.sup.4 and R.sup.5 independently represent a C.sub.1-4 alkyl or haloalkyl group or a C.sub.2-4 alkenyl or haloalkenyl group, or together with the interjacent carbon atom, represents a C.sub.4-8 cycloalkyl or cycloalkenyl ring which is optionally substituted with one or more substituents independently selected from halogen atoms and C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl and C.sub.2-4 haloalkenyl groups.
- 11. A method as claimed in claim 1 wherein the compound is of formula (II) ##STR19## or a salt thereof in which R, R.sup.1, R.sup.2, R.sup.3, R.sup.7, and R.sup.8 and n are as defined in formula I and R.sup.4 and R.sup.5 each independently represent a halogen or an optionally substituted alkyl or alkenyl group.
- 12. A method as claimed in claim 11, wherein n is 0; R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 are both .dbd.O; R.sup.4 and R.sup.5 each independently represent a C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.2-4 alkenyl or C.sub.2-4 haloalkyl group.
- 13. A method as claimed in claim 11, wherein --CHR.sup.4 R.sup.5 represents a methyl or ethyl group.
- 14. A method as claimed in claim 1, wherein the compound is of formula (III) ##STR20## wherein n, m, A, R, R.sup.1, R.sup.2, R.sup.3, R.sup.7 and R.sup.8 are as defined for formula (I);
- and R.sup.4 and R.sup.5 together with the interjacent carbon atom represent an optionally substituted C.sub.4-8 cycloalkyl or cycloalkenyl ring.
- 15. A method as claimed in claim 14, wherein R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 are both .dbd.O; n and m are 0; and R.sup.4 and R.sup.5 together with the interjacent carbon atom represents a fully saturated C.sub.4-8 cycloalkyl ring which is optionally substituted.
- 16. A method as claimed in claim 11, wherein the compound is of formula (IV) ##STR21## or a salt thereof wherein n, A, R, R.sup.1, R.sup.2, R.sup.3, R.sup.7, and R.sup.8 are as defined for formula (I); and
- R.sup.4 and R.sup.5 each independently represent a halogen or optionally substituted alkyl or alkenyl group.
- 17. A method as claimed in claim 16, wherein R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 are both .dbd.O; m is 1 and A is a C.sub.1-6 alkyl or C.sub.2-6 alkenyl chain, which may be substituted by halogen or a branch alkyl or alkenyl chain which may be halogenated.
- 18. A method as claimed in claim 16, wherein R.sup.4 and R.sup.5 are independently selected from the group consisting of C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.2-6 alkenyl and C.sub.2-6 haloalkenyl.
- 19. A method as claimed in claim 16, wherein A is group --(CH.sub.2).sub.a -- wherein a is an integer from 1 to 6 or --(CH.sub.2).sub.a --CH.dbd.CH--(CH.sub.2).sub.b -- where a and b are integers which add up to 0 to 4, or an analogue of these wherein one or more of the carbon atoms in these groups are substituted by alkyl, haloalkyl, alkenyl, haloalkenyl or halogen.
- 20. A method as claimed in claim 19, wherein a is an integer from 1 to 4 or a and b are integers which add up to 0 to 2.
- 21. A compound of formula (VI) ##STR22## wherein m, n, A, R and R.sup.3 are as defined for formula (I) in claim 1 and R.sup.20 is selected from the group consisting of C.sub.1-4 alkyl, C.sub.2-4 alkenyl and C.sub.2-4 haloalkenyl.
- 22. A compound of formula (VII) ##STR23## wherein m, A and R.sup.3, are as defined for formula (I) in claim 1, and R.sup.4 and R.sup.5 independently represent a C.sub.1-7 alkyl or haloalkyl group or C.sub.2-7 alkenyl or haloalkenyl group, in which at least one of R.sup.4 and R.sup.5 is a haloalkyl group.
- 23. A compound as claimed in claim 22, wherein A is a C.sub.1-4 alkylene group and one or both of R.sup.4 and R.sup.5 is trifluoromethyl.
- 24. A process for the preparation of a compound of formula (I) comprising reacting an aldehyde corresponding to the group --A--CHR.sup.4 R.sup.5, where --A-- has an aldehyde group at its free end, directly with a compound of formula (V) wherein ##STR24## wherein R, R.sup.3 and n are as defined in formula I, in a polar organic solvent under alkaline conditions, and heating the product under acidic conditions in a non-polar solvent to effect elimination of water.
- 25. A process for the preparation of the compound of formula (I) comprising reacting a compound of the formula (V) ##STR25## in which R, R.sup.3 and n are defined above, with a carboxylic acid CHR.sup.4 R.sup.5 --(A).sub.m --COOH where R.sup.4, R.sup.5, m and A are as defined above, in the presence of a free radical initiator.
- 26. A process for the preparation of a compound of formula (I) comprising reacting a compound of formula (V) with a compound of formula X--(A).sub.m CHR.sup.4 R.sup.5 wherein X is a leaving group that will leave the compound to give a charged radical .sup.+ (A).sub.m --CHR.sup.4 R.sup.5 in the presence of an acid.
- 27. A compound of formula (VIII) ##STR26## wherein R, n and R.sup.3 are as defined for formula (I) in claim 1 and R.sup.20 is selected from the group consisting of C.sub.1-4 alkyl, C.sub.2-4 alkenyl and C.sub.2-4 haloalkenyl.
- 28. A compound according to claim 27 wherein R.sup.20 is methyl.
- 29. A compound according to claim 27, wherein R.sup.20 is t-butyl.
- 30. 2-hydroxy-3-(2-methylcyclohexyl)-naphthalene-1,4-dione.
- 31. 2-hydroxy-3-(3-methylcyclohexyl)-naphthalene-1,4-dione.
- 32. 2-hydroxy-3-(4-methylcyclohexyl)-naphthalene-1,4-dione.
- 33. 2-hydroxy-3-(4-t-butylcyclohexyl)-naphthalene-1,4-dione.
- 34. A method of combating fungal pests at a locus, which comprises treating the locus with a compound of formula (VIII) as defined in claim 27.
- 35. A method of combating fungal pests at a locus, which comprises treating the locus with a compound of formula (VI) as defined in claim 21.
- 36. A method of combating fungal pests at a locus, which comprises treating the locus with a compound of formula (VII) as defined in claim 22.
- 37. A method as claimed in claim 34 wherein the use is against fungi of Rhizoctonia, Pyricularia and/or Aspergillus.
- 38. A method as claimed in claim 34 wherein the use is against R. solani, P. oryzae or A. niger.
- 39. A method as claimed in claim 35 wherein the use is against fungi of Rhizoctonia, Pyricularia and/or Aspergillus.
- 40. A method as claimed in claim 35 wherein the use is against R. solani, P. oryzae or A. niger.
- 41. A method as claimed in claim 36 wherein the use is against fungi of Rhizoctonia, Pyricularia and/or Aspergillus.
- 42. A method as claimed in claim 36 wherein the use is against R. solani, P. oryzae or A. niger.
Priority Claims (3)
Number |
Date |
Country |
Kind |
9500389 |
Jan 1995 |
GBX |
|
9513584 |
Jul 1995 |
GBX |
|
9513594 |
Jul 1995 |
GBX |
|
Parent Case Info
This is a continuation of PCT application No. PCT/GB96/00041, filed Jan. 10, 1996 PCT application No. 60/001,099 filed Nov. 13, 1995.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
2398418 |
Fieser |
Apr 1946 |
|
2572946 |
Paulshock |
Oct 1951 |
|
Foreign Referenced Citations (5)
Number |
Date |
Country |
0 002228 |
Jun 1979 |
EPX |
0300218 |
Jan 1989 |
EPX |
2323 676 |
Apr 1977 |
FRX |
2520739 |
Nov 1975 |
DEX |
WO 9532176 |
Nov 1995 |
WOX |
Continuations (1)
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Number |
Date |
Country |
Parent |
PCTGB9600041 |
Jan 1996 |
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