Patent GB-1307250-A (GB)
Title: Benzene derivatives
IPC: C07D295/15
Filed: 1970-06-16
Abstract: 1307250 Thiourea derivatives MAY & BAKER Ltd 16 June 1971 [16 June 1970 22 June 1970 26 June 1970 4 Sept 1970 21 Oct 1970 11 Dec 1970 25 March 1971 31 March 1971 1 April 1971 (3)] 29259/70 30244/70 31209/70 42609/70 50000/70 59111/70 7850/71 8292/71 8462/71 8463/71 and 8466/71 Heading C2C [Also in Division A5] The invention comprises novel therapeutic and agricultural fungicidal compounds (I) wherein R<SP>5</SP> represents a group (wherein R<SP>7</SP> represents a straight- or branchedchain aliphatic hydrocarbon group containing not more than 4 carbon atoms which may be saturated or unsaturated and which may optionally be substituted by a halogen atom or an alkoxy group containing not more than 4 carbon atoms, and R<SP>8</SP> represents a hydrogen atom or a methyl group), R<SP>6</SP> represents a hydrogen or a halogen atom, or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, an alkanoylamino group containing 1 to 4 carbon atoms in which the alkanoyl moiety may be straight- or branched-chain and may optionally be substituted by a cycloalkyl group containing from 3 to 6 carbon atoms, an alkoxycarbonylamino group containing from 2 to 4 carbon atoms in which the alkoxy moiety may be straight- or branched-chain, a straight- or branched-chain alkanoyl group containing from 2 to 4 carbon atoms, a benzoyl group or a group and Y represents a group falling within the definition of the symbol R<SP>5</SP>, a nitro group or a group -NR<SP>9</SP>R<SP>10</SP> [wherein R<SP>9</SP> and R<SP>10</SP> each represent a hydrogen atom, or R<SP>9</SP> represents a hydrogen atom or a methyl group and R<SP>10</SP> represents a straight- or branched-chain alkanoyl group containing 1 to 4 carbon atoms (which may optionally be substituted by a cycloalkyl group containing from 3 to 6 carbon atoms), a straight- or branched-chain alkoxycarbonyl group containing 2 to 4 carbon atoms, or a group -COA<SP>1</SP>Z<SP>1</SP>, wherein A<SP>1</SP> represents a straight chain aliphatic hydrocarbon group containing not more than 4 carbon atoms which may be saturated or unsaturated and may optionally be substituted by at least one methyl group, and Z<SP>1</SP> represents a carboxy group or a group of the general formula wherein R<SP>11</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, R<SP>12</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms or a phenylalkyl group with 1 or 2 carbon atoms in the alkyl moiety, and R<SP>13</SP> represents a hydrogen atom or a straight- or branched-chain alkyl group containing not more than 4 carbon atoms, or R<SP>12</SP> and R<SP>13</SP> together with the nitrogen atom to which they are attached form a 5-, 6- or 7- membered heterocyclic ring which may contain in the ring one or two further hetero atoms selected from oxygen, nitrogen and sulphur and which may optionally be substituted by one or more C 1  to C 6  alkyl groups and X<SP>2</SP># is an anion] and, where Yis primary amino, acid addition salts thereof, with the provisos that (i) when R<SP>5</SP> and Y each represent a group -N(R<SP>8</SP>)CSNHCOOR<SP>7</SP>, in which R<SP>8</SP> is a hydrogen atom or a methyl group and R<SP>7</SP> is an alkyl group containing not more than 4 carbon atoms, or an alkyl group of ] or 2 carbon atoms substituted by a halogen atom or methoxy group, or an alkenyl or alkynyl group of 2 or 3 carbon atoms, R<SP>6</SP> is other than a hydrogen or halogen atom or a methyl group; or (ii) when R<SP>5</SP> is a group - NHCSNHCOOR<SP>7</SP> in which R<SP>7</SP> is an alkyl group containing not more than 4 carbon atoms, and (a) Y is a group -NR<SP>9</SP>R<SP>10</SP> in which R<SP>9</SP> is a hydrogen atom or a methyl group and R<SP>10</SP> is an alkanoyl group containing 1 to 3 carbon atoms, a cyclopropylcarbonyl group or an alkoxycarbonyl group containing 2 or 3 carbon atoms, R<SP>6</SP> is other than a hydrogen or chlorine atom or a methyl group, or (b) Y is a group -NR<SP>9</SP>R<SP>10</SP> in which R<SP>9</SP> and R<SP>10</SP> each represents a hydrogen atom, R<SP>6</SP> is other than a hydrogen or halogen atom or methyl group; or (iii) when R<SP>5</SP> is a group -NHCSNHCOOR<SP>7</SP> in which R<SP>7</SP> is an alkyl group containing not more than 4 carbon atoms and Y is a nitro group, R<SP>6</SP> is other than a hydrogen or chlorine atom or a methyl group or, when R<SP>6</SP> is in o-position in relation to R<SP>5</SP>, R<SP>6</SP> is additionally other than an alkanoylamino group containing 1 to 3 carbons, a cyclopropyl carbonamido group or an alkoxycarbonylamino group containing 2 or 3 carbons. They are obtained by standard methods utilizing compounds II to XII (X<SP>3</SP> is Br, Cl or I).