Imperial Chemical Industries Limited

Raymond L Sunley

Raymond Elliott

Alan J Whittle

Roger Salmon

Ian T Kay

Terence Lewis

Trevor R Perrior

David A Griffin

John Dalziel

Geoffrey David Snowling

Harjinder S Bansal

Phenyl substituted heterocyclic compounds having insecticidal activity have the formula (I): ##STR1## wherein R.sup.1 is an optionally substituted pyridone, thiopyridone, pyrimidinthione, pyrimidinone, pyrazole, imidazole or triazole group; R.sup.2 is hydrogen, halogen, haloalkyl, nitro, cyano or a group --CX--NY.sup.1 Y.sup.2 ; R.sup.3 and R.sup.5 are hydrogen, halogen, alkyl or cycloalkyl; R.sup.4 is halogen, haloalkyl, haloalkoxy or S(O).sub.n R.sup.6 ; and Y.sup.1 and Y.sup.2 are independently selected from hydrogen, nitro, amino or optionally substituted alkyl or Y.sup.1 and Y.sup.2 together with the nitrogen to which they are attached form an aliphatic heterocyclic group or form the group .dbd.CHY.sup.3 or Y.sup.1 is hydrogen and Y.sup.2 is alkoxycarbonyl, alkylcarbonyl, optionally substituted aralkyl or --S(O).sub.n R.sup.6.

1-phenyl substituted pyrimidone derivatives

A compound of formula (I): ##STR1## wherein R.sup.1 and R.sup.2 are independently selected from hydrogen, halogen, haloalkyl, alkoxy or nitro, provided that R.sup.1 and R.sup.2 are not both nitro; R.sup.3 and R.sup.4 are independently selected from hydrogen, halogen, alkyl or cycloalkyl; R.sup.5 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.6 is halogen, nitro, haloalkyl, haloalkoxy or --S(O).sub.n R.sup.10 ; R.sup.7 is hydrogen, halogen, hydroxyalkyl, cyano, nitro, alkoxy, --S(O).sub.n R.sup.10, NR.sup.11 R.sup.12, haloalkyl or formyl; R.sup.8 is hydrogen, halogen, NR.sup.11 R.sup.12, alkyl, cycloalkyl or S(O).sub.n R.sup.10 ; and R.sup.9 is oxygen or sulphur; where n is 0, 1 or 2; and R.sup.10 is alkyl, haloalkyl or cycloalkyl; and R.sup.11 and R.sup.12 are independently selected from hydrogen, alkyl or cycloalkyl or R.sup.11 and R.sup.12 together with the nitrogen to which they are attached form a heterocyclic group; provided that when R.sup.5 is trifluoromethyl at least one of the following applies:

1-phenyl-6-one-pyrimidine derivatives

A method of killing or controlling unwanted plants by applying to the plant on to a locus thereof an effective amount of a compound of formula (I) ##STR1## or a salt thereof: wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyl, halogen, cyano, nitro, haloalkyl and haloalkoxy; R.sup.6 is hydrogen, hydroxy, amino, lower alkyl, halogen, cyano, haloalkyl, nitro, aryl, or a group C(O).sub.m R.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, alkynyl or phenyl any of which may be optionally substituted and m is 1 or 2; R.sup.7 is hydrogen, lower alkyl, haloalkyl, C(O).sub.m R.sup.10 or halogen; or R.sup.6 and R.sup.7 together form an optionally substituted alkylene chain of 2 or 3 carbon atoms; R.sup.8 is hydrogen, lower alkyl or halogen or the group R.sup.7 and R.sup.8 together form an oxo group; and the group CZR.sup.9 is carboxy or an ester thereof, or R.sup.9 is a group SR.sup.10 or NR.sup.11 R.sup.12 wherein R.sup.11 is hydrogen or alkyl and R.sup.12 is hydrogen, alkyl, S(O).sub.n R.sup.10 wherein n is 0, 1 or 2; or R.sup.9 is a group NR.sup.11 NR.sup.13 R.sup.14 wherein R.sup.11, R.sup.13 and R.sup.14 are independently selected from hydrogen or alkyl; or R.sup.9 is a group --.sym.NR.sup.11 NR.sup.13 R.sup.14 R.sup.20 x.crclbar. wherein R.sup.11, R.sup.13, R.sup.14 and R.sup.20 are each hydrogen or alkyl, and x.sup.- is an agriculturally acceptable anion, and z is oxygen or sulphur. Herbicidal compositions containing compounds of formula (I) are also claimed together with certain novel sub groups of compounds of formula (I) and processes for their preparation.

Herbicidal compositions

Triazole compounds useful as plant growth regulators of the formula ##STR1## and stereoisomers thereof, wherein R.sup.1 is selected from alkyl and haloalkyl groups, R.sup.2 is hydrogen, and R.sup.3 is a tertiary butyl group optionally substituted by halogen; and acid addition salts, and metal complexes thereof.

Triazolylmethyl tert-butyl carbinol derivatives which have plant growth

Triazolyl alcohol derivatives active as plant growth regulating have the general formula: ##STR1## wherein R.sup.1 is a cycloalkyl or cycloalkenyl group containing from 3 to 8 ring carbon atoms and optionally substituted, for example by lower alkyl or halogen; n is 0 or 1 or 3; R.sup.2 is hydrogen or lower alkyl; and R.sup.3 is a tertiary butyl group optionally substituted by one or more halogen atoms. Triazol-1-yl derivatives are preferred.

Triazolyl ethanol derivatives as plant growth regulators

A compound having the general formula: ##STR1## and stereoisomers thereof, wherein R.sup.1 is alkyl, alkenyl, alkynyl, cycloalkyl or cycloalkenyl, all having up to 8 carbon atoms; or is aryl, aralkyl or heterocyclyl, any of which may be optionally substituted; R.sup.2 is alkyl, alkenyl, alkynyl, alkynylalkenyl, alkenyl alkynyl, cycloalkyl, cycloalkenyl, or cycloalkylalkyl, all of which contain up to 8 carbon atoms and may be substituted; R.sup.3 and R.sup.4, which can be the same or different, are hydrogen (but are not both hydrogen) or are alkyl of up to 4 carbon atoms, alkoxy of up to 4 carbon atoms, OCF.sub.3, CF.sub.3 or halogen, or together constitute a ring of 3-6 carbon atoms; and Y is .dbd.CH-- or .dbd.N--; and esters, ethers, salts and metal complexes thereof. The compounds are useful as plant growth regulating agents.

Heterocyclic compounds

A process of severely damaging or killing unwanted plants, which comprises applying to the plants, or to the growth medium thereof, a herbicidally effective amount of pyrimidine compound of the formula: ##STR1## or a herbicidal acid addition salt thereof, wherein R.sup.1 is an alkyl radical of 1 to 6 carbon atoms, cycloalkyl or alkenyl; R is a hydrogen atom or an alkyl or alkenyl radical of from 1 to 12 carbon atoms, which may be substituted by a phenyl radical; or R.sup.1 and R taken together form a trimethylene or tetramethylene radical; X is either (a) an --NR.sup.3 R.sup.4 radical wherein each of the groups R.sup.2 and R.sup.4 is a hydrogen atom or an alkyl or alkenyl radical of 1 to 3 carbon atoms or cycloalkyl, or --NR.sup.3 R.sup.4 constitutes a pyrrolidinyl, piperidinyl or morpholinyl ring; or (b) a group --OR.sup.5 wherein R.sup.5 is an alkyl or alkenyl radical of 1 to 10 carbon atoms or cycloalkyl; and R.sup.6 and R.sup.7 each represent hydrogen or an alkyl or alkenyl radical of 1 to 8 carbon atoms, or cycloalkyl, or R.sup.6 and R.sup.7, taken together with the nitrogen atom to which they are attached constitute a pyrrolidinyl, piperidinyl, or morpholinyl ring; provided that R may be hydrogen only when X is an OR.sup.5 group.

Growing community of inventors

Twyford, United Kingdom

Raymond L Sunley