Pesticidal compounds
AssigneeBTG International Limited
InventorsBhupinder Pall Singh Khambay, Duncan Batty, Stuart Cameron, David Gordon Beddie
Life of this patent
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Abstract
This invention relates to 1,1,1,4-substituted naphthaline compounds, compositions, processes for their preparation and processes for their use as pesticides, especially insecticides, acaricides and fungicides.
Drawings
Claims41
1. A compound of formula (I) ##STR17## 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 R9 represents a hydrogen atom or an optionally substituted alkyl group;
- R.sup.3 represents a group OR.sup.10 where R.sup.10 represents a hydrogen atom, an optionally substituted aryl or aralkyl group, or a group --CO--R.sup.11, --CO--O--R.sup.11, --SOR.sup.11, --SO.sub.2 --R.sup.11, --P(X)(OR.sup.12)(OR.sup.13), --P(X)(R.sup.12)(OR.sup.13), --P(OR.sup.12)(OR.sup.13) or --P(R.sup.12)(OR.sup.13) where R.sup.11 represents a hydrogen atom, an optionally substituted alkyl, alkenyl, aryl or aralkyl group or a group-NR.sup.12 R.sup.13 ;
- R.sup.12 and R.sup.13 independently representing a hydrogen atom or an optionally substituted alkyl group and X represents an oxygen or sulfur atom;
- R.sup.6 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy or aryloxy 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;
- R.sub.4 and R.sub.5 each independently represent a halogen atom or an optionally substituted alkyl or alkenyl group, or together with the interjacent carbon atom represent an optionally substituted 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 --CR.sup.4 R.sup.5 R.sup.6 ;
- with the provisos that when R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 are groups .dbd.O and n=0, (i) when R.sup.4 and R5 are methyl, m is 0 and R.sup.6 is ethenyl, then R.sup.3 is not hydroxyl or ethanoyloxy, (ii) when R.sup.4 and R.sup.5 are methyl, m is 0 or m is 1 where A is --CH.sub.2 -- or (CH.sub.2).sub.2 -- and R.sup.3 is hydroxyl, then R.sup.6 is not methyl, (iii) when R.sup.4 and R.sup.5 are methyl, m is 1 where A is --(CH.sub.2).sub.2 -- and R.sup.3 is hydroxyl, then R.sup.6 is not chloro, (iv) when R.sup.4 and R.sup.5 together with the interjacent carbon atom form a cyclohexyl ring, m is 1 where A is --CH.sub.2 and R.sup.3 is hydroxyl, then R.sup.6 is not methyl, (v) when R.sup.4 and R.sup.5 are methyl, m is 1 where A is --CH.sub.2 -- and R.sup.3 is hydroxyl, then R.sup.6 is not hydroxymethyl, and (vi) when m is 0, then R.sup.6 represents a group of C.sub.1-6 carbons in length, or the 2,6-dimethyl-2,6-octadienoate ester thereof.
A compound as claimed in 18 wherein R.sup.4, R.sup.5 and R.sup.6 are independently selected from C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.2-6 alkenyl or C.sub.2-6 haloalkenyl.
A method of combatting pests at a locus which comprises treating the locus with a compound of the formula (I) ##STR21## 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;
- wherein 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 represents a hydrogen atom or an optionally substituted alkyl group;
- R.sup.3 represents a group OR.sup.10 where R.sup.10 represents a hydrogen atom, an optionally substituted aryl and aralkyl group, or a group --CO--R.sup.11, --CO--O--R.sup.11, --SOR.sup.11, --SO.sub.2 --R.sup.11,--P(X)(OR.sup.12)(OR.sup.13), --P(X)(R.sup.12)(OR.sup.13), --P(OR.sup.12)(OR.sup.13) or --P(R.sup.12)(OR.sup.13) where R.sup.11 represents a hydrogen atom, an optionally substituted alkyl, alkenyl, arvl or aralkyl group or a group--NR.sup.12 R.sup.13 ;
- R.sup.12 and R.sup.13 independently representing a hydrogen atom or an optionally substituted alkyl group and X represents an oxygen or sulfur atom;
- R.sup.6 represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy or aryloxy 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 a previously defined;
- and wherein R.sub.4 and R.sub.5 each independently represent a halogen atom or an optionally substituted alkyl or alkenyl group or together with the interjacent carbon atom represent an optionally substituted 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 --CR.sup.4 R.sup.5 R.sup.6;
- with the proviso that when R.sup.1 with R.sup.2, and R.sup.7 with R.sup.8 are groups .dbd.O and n=0, when R.sup.4 and R.sup.5 are methyl, m is 1 A is --CH.sub.2 -- and R.sup.3 is hydroxyl, then R.sup.6 is not hydroxymethyl or the 2,6-dimethyl-2,6-octadienoate ester thereof.
A process for the preparation of a compound of formula (I) wherein m is 0 comprising reacting a compound of the general formula (V) ##STR22## in which n, R and R.sup.3 are as defined in formual (I), with a compound of the general formula (VI) ##STR23## in which X represents a leaving group, R.sup.111, R.sup.121 and R.sup.131 each independently represent a hydrogen atom or an optionally substituted alkyl group and R.sup.4 and R.sup.5 are as defined in formula (I)to produce a compound of the formula (VII) ##STR24## in which n, R, R.sup.111 R.sup.121, R.sup.131, R.sup.4 and R.sup.5 are as defined above;
- and the compound of formula (VII) is then heated in a suitable solvent to effect a Claisen-type rearrangement resulting in a compound of the formula (VIII) ##STR25##
A process for the preparation of a compound of formula (I) which compromises reacting an aldehyde A--CR.sup.4 R.sup.5 R.sup.6, where A, R.sup.4, R.sup.5 and R.sup.6 are as defined for formula I and A has an aldehyde group at the free end of the acyclic carbon chain instead of the 3-position of the napthalene ring, directly with the compound of formula (V) in a polar organic solvent under alkaline conditions, and then heating the product under acidic conditions in a non-polar solvent to effect elimination of water.
A process for the preparation of a compound of formula (I) comprising reacting a compound of the general formula (V) in which n, R and R.sup.3 are as defined above, with a carboxylic acid CR.sup.4 R.sup.5 R.sup.6 --(A).sub.m --COOH where A, m, R.sup.4, R.sup.5 and R.sup.6 are as defined for formula I, in the presence of a free radical initiator.
A process for the preparation of a compound of formula (I) comprising reacting a compound of the general formula (V) ##STR26## with a compound of general formula X--(A).sub.m --CR.sup.4 R.sup.5 R.sup.6, wherein A, m, R.sup.4, R.sup.5 R.sup.6 are as defined for formula I and X is a leaving group that leaves to provide the radical .sup.+ --(A).sub.m --CR.sup.4 R.sup.5 R.sup.6, in the presence of an acid.
A composition comprising a compound of formula (I) as defined above, in association with at least one carrier.
A compound of formula (VII) ##STR27## wherein n, R, R.sup.4 and R.sup.5 are as defined in claim, R.sup.111, R.sup.121 and R.sup.131 each independently represents a hydrogen atom or an optionally substituted alkyl group.
Dependencies are inferred from the claim text.