# US 4,399,148 A · Hydroxyarylalkyleneaminoaryl carbamates and derivatives thereof useful as insecticidal compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,399,148 A - Document ID: US4399148A - Status: Granted - Kind: A - Application number: 06/247,369 - Filed: 1981-03-25 - Granted: 1983-08-16 - Earliest claimed: 1981-03-25 - Assignees: Union Carbide Corporation - Inventors: Charles A. Wilson, II - Web page: https://patentgrep.com/patent/US4399148A ## CPC - A01N 47/24: containing the groups [IMAGE cpc-sch-A01N-0944.gif], [IMAGE cpc-sch-A01N-0945.gif] or[IMAGE cpc-sch-A01N-0946.gif]; Thio analogues thereof - A01N 47/22: O-Aryl or S-Aryl esters thereof - C07D 307/86: with an oxygen atom directly attached in position 7 - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) ## Abstract This invention relates to novel hydroxyarylalkyleneaminoaryl carbamate compounds and derivatives thereof and to their preparation. This invention is also directed to insecticidal compositions comprising an acceptable carrier and an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention as well as to a method of controlling insects by subjecting them to an insecticidally effective amount of a hydroxyarylalkyleneaminoaryl carbamate compound or derivative of this invention. ## Claims ### Claim 1 A compound of the formula: ##STR31## wherein R and R.sup.1 are individually hydrogen or alkyl; R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further than when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl hydroxyarylalkyleneaminoaryloxycarbonylaminosulphenyl, hydroxy arylalklyleneamino-aryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination; and metal salts thereof. ### Claim 2 (depends on 1) A compound according to claim 1 wherein R and R.sup.1 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive. ### Claim 3 (depends on 1) A compound according to claim 1 wherein R is hydrogen or methyl. ### Claim 4 (depends on 1) A compound according to claim 1 wherein R.sup.1 is hydrogen, methyl or isopropyl. ### Claim 5 (depends on 1) A compound according to claim 1 wherein R.sup.2 is hydrogen, halo or alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy having from 1 to 6 carbon atoms inclusive. ### Claim 6 (depends on 1) A compound according to claim 1 wherein R.sup.2 is hydrogen, chloro, methyl or isopropyl. ### Claim 7 (depends on 1) A compound according to claim 1 wherein when R.sup.1 and R.sup.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 8 (depends on 1) A compound according to claim 1 wherein when R.sup.1 and R.sup.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together form a three-membered bridge consisting of two carbon atoms and one oxygen atom in which the carbon atoms may optionally be substituted with methyl. ### Claim 9 (depends on 1) A compound according to claim 1 wherein when R.sup.1 and R.sup.2 are alkyl and located adjacent to each other, then R.sup.1 and R.sup.2 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 10 (depends on 1) A compound according to claim 1 wherein R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio having from 1 to 6 carbon atoms inclusive. ### Claim 11 (depends on 1) A compound according to claim 1 wherein R.sup.3 is hydrogen, bromo, chloro, nitro or methoxy. ### Claim 12 (depends on 1) A compound according to claim 1 wherein R.sup.4 is hydrogen or methylcarbamoyloxy. ### Claim 13 (depends on 1) A compound according to claim 1 wherein when R.sup.3 and R.sup.4 are individually alkyl having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a bridge of from three to five carbon atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 14 (depends on 1) A compound according to claim 1 wherein when R.sup.3 and R.sup.4 are alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 15 (depends on 1) A compound according to claim 1 wherein R.sup.5 and R.sup.6 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive provided that when R.sup.5 is alkyl having from 1 to 6 carbon atoms inclusive, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxcarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination. ### Claim 16 (depends on 1) A compound according to claim 1 wherein when R.sup.5 is methyl, then R.sup.6 is hydrogen, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxycarbonyl(N-methylamino)-s ulfenyl, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxycarbonyl(N-methylamino)th iosulfenyl, tert-butylthiosulfenyl, tert-butylphenylsulfenyl or dibutylaminosulfenyl. ### Claim 17 (depends on 1) A compound according to claim 1 wherein the metal salts thereof are selected from the group consisting of sodium, potassium, lithium, magnesium, calcium, molybdenum, chromium, aluminum, manganese, iron, cobalt, nickel, copper and zinc salts. ### Claim 18 (depends on 1) A compound according to claim 1 wherein the metal salt thereof is copper (II) salt. ### Claim 19 4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 20 4-(2-Hydroxy-5-methoxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 21 4-(2-Hydroxybenzylideneamino)-3-isopropylphenyl methylcarbamate. ### Claim 22 4-(3,5-Dibromo-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 23 4-(5-Chloro-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 24 4-(2-Hydroxy-5-nitrobenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 25 Di[4-(2-hydro xybenzylideneamino)-3,5-dimethylphenyl]thiobis(methylcarbamate). ### Claim 26 2,3-Dihydro-2,2-dimethyl-4-(2-hydroxybenzylideneamino)benzofuran-7-yl methylcarbamate. ### Claim 27 4-[2-Hydroxy-4-(methylcarbamoyloxy)benzylideneamino]-3,5-dimethylphenyl methylcarbamate. ### Claim 28 4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl N-(4-tert-butylphenylsulfenyl)-N-methylcarbamate. ### Claim 29 4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate. ### Claim 30 4-(2-Hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate, copper (II) salt. ### Claim 31 An insecticidal composition comprising an acceptable carrier and as the active toxicant an insecticidally effective amount of a compound of the formula: ##STR32## wherein R and R.sup.1 are individually hydrogen or alkyl; R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five-membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination; and metal salts thereof. ### Claim 32 (depends on 31) A composition according to claim 31 wherein R and R.sup.1 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive. ### Claim 33 (depends on 31) A composition according to claim 31 wherein R is hydrogen or methyl. ### Claim 34 (depends on 31) A composition according to claim 31 wherein R.sup.1 is hydrogen, methyl or isopropyl. ### Claim 35 (depends on 31) A composition according to claim 31 wherein R.sup.2 is hydrogen, halo or alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy having from 1 to 6 carbon atoms inclusive. ### Claim 36 (depends on 31) A composition according to claim 31 wherein R.sup.2 is hydrogen, chloro, methyl or isopropyl. ### Claim 37 (depends on 31) A composition according to claim 31 wherein when R.sup.1 and R.sup.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five-membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 38 (depends on 31) A composition according to claim 31 wherein when R.sup.1 and R.sup.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together form a three-membered bridge consisting of two carbon atoms and one oxygen atom in which the carbon atoms may optionally be substituted with methyl. ### Claim 39 (depends on 31) A composition according to claim 31 wherein when R.sup.1 and R.sup.2 are alkyl and located adjacent to each other, then R.sup.1 and R.sup.2 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 40 (depends on 31) A composition according to claim 31 wherein R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio having from 1 to 6 carbon atoms inclusive. ### Claim 41 (depends on 31) A composition according to claim 31 wherein R.sup.3 is hydrogen, bromo, chloro, nitro or methoxy. ### Claim 42 (depends on 31) A composition according to claim 31 wherein R.sup.4 is hydrogen or methylcarbamoyloxy. ### Claim 43 (depends on 31) A composition according to claim 31 wherein when R.sup.3 and R.sup.4 are individually alkyl having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further than when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 44 (depends on 31) A composition according to claim 31 wherein when R.sup.3 and R.sup.4 are alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 45 (depends on 31) A composition according to claim 31 wherein R.sup.5 and R.sup.6 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive provided that when R.sup.5 is alkyl having from 1 to 6 carbon atoms inclusive, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination. ### Claim 46 (depends on 31) A composition according to claim 31 wherein when R.sup.5 is methyl, then R.sup.6 is hydrogen, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxycarbonyl(N-methylamino)su lfenyl, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxycarbonyl(N-methylamino)-t hiosulfenyl, tert-butylthiosulfenyl, tert-butylphenylsulfenyl or dibutylaminosulfenyl. ### Claim 47 (depends on 31) A composition according to claim 31 wherein the metal salts of the active toxicant are selected from the group consisting of sodium, potassium, lithium, magnesium, calcium, molybdenum, chromium, aluminum, manganese, iron, cobalt, nickel, copper and zinc salts. ### Claim 48 (depends on 31) A composition according to claim 31 wherein the metal salt of the active toxicant is copper (II) salt. ### Claim 49 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 50 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxy-5-methoxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 51 (depends on 31) A combination according to claim 31 wherein the active toxicant is 4-(2-hydroxybenzylideneamino)-3-isopropylphenyl methylcarbamate. ### Claim 52 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(3,5-dibromo-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 53 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(5-chloro-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 54 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxy-5-nitrobenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 55 (depends on 31) A composition according to claim 31 wherein the active toxicant is di[4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl]thiobis(methylcarbamat e). ### Claim 56 (depends on 31) A composition according to claim 31 wherein the active toxicant is 2,3-dichloro-2,2-dimethyl-4-(2-hydroxybenzylideneamino)benzofuran-7-yl methylcarbamate. ### Claim 57 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-[2-hydroxy-4-(methylcarbamoyloxy)benzylideneamino]-3,5-dimethylphenyl methylcarbamate. ### Claim 58 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(4-tert-butylphenylsulfenyl)-N-methylcarbamate. ### Claim 59 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl N-(tert-butylthiosulfenyl)-N-methylcarbamate. ### Claim 60 (depends on 31) A composition according to claim 31 wherein the active toxicant is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate, copper (II) salt. ### Claim 61 A method of controlling insects which comprises subjecting them to an insecticidally effective amount of a compound of the formula: ##STR33## wherein R and R.sup.1 are individually hydrogen or alkyl; R.sup.2 is hydrogen, halo, alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy provided that when R.sup.1 and R.sup.2 are individually alkyl or alkoxy and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five-membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that then the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio provided that when R.sup.3 and R.sup.4 are individually alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five-membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic; and R.sup.5 and R.sup.6 are individually hydrogen or alkyl provided that when R.sup.5 is alkyl, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, cholor, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination; and metal salts thereof. ### Claim 62 (depends on 61) A method according to claim 61 wherein R and R.sup.1 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive. ### Claim 63 (depends on 61) A method according to claim 61 wherein R is hydrogen or methyl. ### Claim 64 (depends on 61) A method according to claim 61 wherein R.sup.1 is hydrogen, methyl or isopropyl. ### Claim 65 (depends on 61) A method according to claim 61 wherein R.sup.2 is hydrogen, halo or alkyl, alkoxy, alkenyl, alkylthioalkyl or alkenyloxy having from 1 to 6 carbon atoms inclusive. ### Claim 66 (depends on 61) A method according to claim 61 wherein R.sup.2 is hydrogen, chloro, methyl or isopropyl. ### Claim 67 (depends on 61) A method according to claim 61 wherein when R.sub.1 and R.sub.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together may form a three-to-five membered bridge consisting of carbon atoms or carbon and oxygen atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 68 (depends on 61) A method according to claim 61 wherein when R.sup.1 and R.sup.2 are alkyl or alkoxy having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.1 and R.sup.2 together form a three-membered bridge consisting of two carbon atoms and one oxygen atom in which the carbon atoms may optionally be substituted with methyl. ### Claim 69 (depends on 61) A method according to claim 61 wherein when R.sup.1 and R.sup.2 are alkyl and located adjacent to each other, then R.sup.1 and R.sup.2 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 70 (depends on 61) A method according to claim 61 wherein R.sup.3 and R.sup.4 are individually hydrogen, halo, nitro, cyano, hydroxy, unsubstituted or aliphatically substituted phenyl or phenoxy, alkyl, alkoxy, alkylcarbamoyloxy or alkylthio having from 1 to 6 carbon atoms inclusive. ### Claim 71 (depends on 61) A method according to claim 61 wherein R.sup.3 is hydrogen, bromo, chloro, nitro or methoxy. ### Claim 72 (depends on 61) A method according to claim 61 wherein R.sup.4 is hydrogen or methylcarbamoyloxy. ### Claim 73 (depends on 61) A method according to claim 61 wherein when R.sup.3 and R.sup.4 are individually alkyl having from 1 to 6 carbon atoms inclusive and located adjacent to each other, then R.sup.3 and R.sup.4 together may form a three-to-five-membered bridge consisting of carbon atoms in which the carbon atoms may be optionally substituted with alkyl having from 1 to 4 carbon atoms inclusive and provided further that when the bridge consists of four carbon atoms, the resulting six-membered ring may optionally be aromatic or substituted aromatic. ### Claim 74 (depends on 61) A method according to claim 61 wherein when R.sup.3 and R.sup.4 are alkyl and located adjacent to each other, then R.sup.3 and R.sup.4 together form a four-membered bridge consisting of carbon atoms and the resulting six-membered ring is aromatic. ### Claim 75 (depends on 61) A method according to claim 61 wherein R.sup.5 and R.sup.6 are individually hydrogen or alkyl having from 1 to 6 carbon atoms inclusive provided that when R.sup.5 is alkyl having from 1 to 6 carbon atoms inclusive, then R.sup.6 may also be alkanoyl, haloalkanoyl, haloalkylsulfenyl, dialkylaminosulfenyl, morpholinosulfenyl or either substituted or unsubstituted cycloalkylsulfenyl, cycloalkylthiosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminosulfenyl, hydroxyarylalkyleneaminoaryloxycarbonylaminothiosulfenyl, alkylsulfenyl, phenylsulfenyl, alkylthiosulfenyl or phenylthiosulfenyl wherein the permissible substituents are one or more fluoro, chloro, bromo, cyano, aroyl, nitro, alkyl, alkanoyl, alkoxy, phenyl, phenoxy or trihalomethyl substituents in any combination. ### Claim 76 (depends on 61) A method according to claim 61 wherein when R.sup.5 is methyl, then R.sup.6 is hydrogen, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxycarbonyl(N-methylamino)-s ulfenyl, 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenoxcarbonyl(N-methylamino)thi osulfenyl, tert-butylthiosulfenyl, tert-butylpenylsulfenyl or dibutylaminosulfenyl. ### Claim 77 (depends on 61) A method according to claim 61 wherein the metal salts of the compound are selected from the group consisting of sodium, potassium, lithium, magnesium, calcium, molybdenum, chromium, aluminum, manganese, iron, cobalt, nickel, copper and zinc salts. ### Claim 78 (depends on 61) A method according to claim 61 wherein the metal salt of the compound is copper (II) salt. ### Claim 79 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 80 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxy-5-methoxybenzylideneamino)3,5-dimethylphenyl methylcarbamate. ### Claim 81 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxybenzylideneamino)-3-isopropylphenyl methylcarbamate. ### Claim 82 (depends on 61) A method according to claim 61 wherein the compound is 4-(3,5-dibromo-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 83 (depends on 61) A method according to claim 61 wherein the compound is 4-(5-chloro-2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 84 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxy-5-nitrobenzylideneamino)-3,5-dimethylphenyl methylcarbamate. ### Claim 85 (depends on 61) A method according to claim 61 wherein the compound is di[4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl]thiobis(methylcarbamat e). ### Claim 86 (depends on 61) A method according to claim 61 wherein the compound is 2,3-dichloro-2,2-dimethyl-4-(2-hydroxybenzylideneamino)benzofuran-7-yl methylcarbamate. ### Claim 87 (depends on 61) A method according to claim 61 wherein the compound is 4-[2-hydroxy-4-(methylcarbamoyloxy)benzylideneamino]-3,5-dimethylphenyl methylcarbamate. ### Claim 88 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl-N-(4-tert-butylphenylsulf enyl)-N-methylcarbamate. ### Claim 89 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl-N-(tert-butylthiosulfenyl )-N-methylcarbamate. ### Claim 90 (depends on 61) A method according to claim 61 wherein the compound is 4-(2-hydroxybenzylideneamino)-3,5-dimethylphenyl methylcarbamate, copper (II) salt.