Ketoalkanesulfenyl and ketoalkanethiosulfenyl carbamates

Claim 2

A compound of the formula: ##STR52## wherein: n is 1 or 2; R 1 is alkyl; R 2 is alkyl or chlorine; R 3 is hydrogen, alkyl, phenyl, alkoxycarbonyl, alkanoyl or phenoxycarbonyl; R 4 is hydrogen, phenoxy, alkyl, alkoxy or phenyl; R 3 and R 4 together may form an alkylene chain completing a five or six membered alicyclic ketone or dione; R 5 is: A. naphthyl, benzofuranyl, benzothienyl, indanyl or phenyl; or B. phenyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, alkyl, alkynyloxy, alkoxy, dioxalanyl, dialkylamino, alkoxycarbonylamino, dicyanoethylidene, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dithiolanyl or dialkylaminomethyleneimino groups; or ##STR53## R 6 and R 7 are individually hydrogen, cyano, chloro, alkyl, phenyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl, cyanoalkylthio alkanoyl or aminocarbonylalkylthio groups; and A is a divalent alkylene chain completing a five or six membered alicyclic ring which includes up to three hetero atoms selected from among oxygen, sulfur, sulfinyl, sulfonyl, aminocarbonyl or alkylaminocarbonyl provided that not more than one or said hetero atoms may be aminocarbonyl or alkylaminocarbonyl; with the proviso that: A. The total number of aliphatic carbon atoms included in R 1 , R 2 , R 3 , R 4 , R 6 and R 7 individually may not exceed six; and B. At least one R 3 or R 5 , substituent includes an oxocarbonyl, heterocyclic function or cyano group.

Claim 3

A compound according to claim 1 wherein R 1 is methyl and the total number of aliphatic carbons included in any one R 2 , R 3 , R 4 , R 6 or R 7 substituent may not exceed four.

Claim 4

A compound according to claim 1 wherein n is 1.

Claim 5

A compound according to claim 1 wherein n is 2.

Claim 6

A compound according to claim 1 wherein R 1 is methyl.

Claim 7

A compound according to claim 1 wherein R 1 is methyl.

Claim 8

A compound according to claim 1 wherein R 2 is alkyl.

Claim 9

A compound according to claim 1 wherein R 2 is methyl.

Claim 10

A compound according to claim 1 wherein R 3 and R 4 are alkyl.

Claim 11

A compound according to claim 1 wherein R 3 and R 4 are phenyl.

Claim 12

A compound according to claim 1 wherein R 4 is isopropyl.

Claim 13

A compound according to claim 1 wherein R 3 is methyl.

Claim 14

A compound according to claim 1 wherein R 5 is naphthyl, benzofuranyl, phenyl or substituted phenyl.

Claim 15

A compound according to claim 1 wherein R 6 and R 7 are individually hydrogen, cyano, alkyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl or cyanoalkylthio.

Claim 16

A compound according to claim 1 wherein A is a divalent aliphatic chain completing a 1,4-dithiane, 1,3-dithiolane, 1,4-thiazine-3-one, 1,4-oxazine-3-one, 1,3-5-trithiane, 1,3,5-oxadithiane, 1,4-oxathiane, 1,3-oxathiolane, 1,3-thiazolidin-4-one, or thiophane ring wherein sulfur may be in any of its oxidation states or in any combination thereof.

Claim 17

2-[[0-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl) carbamoyl]] -1,4-dithiane.

Claim 18

2-[[0-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl) carbamoyl]] -1,4-dithiane.

Claim 19

7[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran.

Claim 20

7[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran.

Claim 21

An insecticidal, miticidal and nematocidal composition comprising an acceptable carrier and an insecticidally, miticidally or nematocidally effective amount of a compound of the formula: ##STR54## wherein: n is 1 or 2; R 1 is alkyl; R 2 is alkyl or chlorine; R 3 is hydrogen, alkyl, phenyl, alkoxycarbonyl, alkanoyl or phenoxycarbonyl; R 4 is hydrogen, phenoxy, alkyl, alkoxy or phenyl; R 3 and R 4 together may form an alkylene chain completing a five or six membered alicyclic ketone or dione; R 5 is: A. naphthyl, benzofuranyl, benzothienyl, indanyl or phenyl; or B. phenyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, alkyl, alkynyloxy, alkoxy, dioxalanyl, dialkylamino, alkoxycarbonylamino, dicyanoethylidene, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dithiolanyl or dialkylaminomethyleneimino groups; and ##STR55## wherein: R 6 and R 7 are individually hydrogen, cyano, chloro, alkyl, phenyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl, cyanoalkylthio alkanoyl or aminocarbonylalkylthio groups; and D. A is a divalent alkylene chain completing a five or six membered alicyclic ring which includes up to three hetero atoms selected from among oxygen, sulfur, sulfinyl, sulfonyl, aminocarbonyl or alkylaminocarbonyl provided that not more than one of said hetero atoms may be aminocarbonyl or alkylaminocarbonyl; With the proviso that: A. The total number of aliphatic carbon atoms included in R 1 , R 2 , R 3 , R 4 , R 6 and R 7 substituents individually may not exceed six; and B. At least one R 3 or R 5 , substituent includes an oxocarbonyl group, a heterocyclic group or a cyano group.

Claim 22

An insecticidal, miticidal and nematocidal composition comprising an acceptable carrier and an insecticidally, miticidally or nematocidally effective amount of a compound of the formula: ##STR54## wherein: n is 1 or 2; R 1 is alkyl; R 2 is alkyl or chlorine; R 3 is hydrogen, alkyl, phenyl, alkoxycarbonyl, alkanoyl or phenoxycarbonyl; R 4 is hydrogen, phenoxy, alkyl, alkoxy or phenyl; R 3 and R 4 together may form an alkylene chain completing a five or six membered alicyclic ketone or dione; R 5 is: A. naphthyl, benzofuranyl, benzothienyl, indanyl or phenyl; or B. phenyl substituted with one or more chloro, bromo, fluoro, nitro, cyano, alkyl, alkynyloxy, alkoxy, dioxalanyl, dialkylamino, alkoxycarbonylamino, dicyanoethylidene, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, dithiolanyl or dialkylaminomethyleneimino groups; and ##STR55## wherein: R 6 and R 7 are individually hydrogen, cyano, chloro, alkyl, phenyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl, cyanoalkylthio alkanoyl or aminocarbonylalkylthio groups; and D. A is a divalent alkylene chain completing a five or six membered alicyclic ring which includes up to three hetero atoms selected from among oxygen, sulfur, sulfinyl, sulfonyl, aminocarbonyl or alkylaminocarbonyl provided that not more than one of said hetero atoms may be aminocarbonyl or alkylaminocarbonyl; With the proviso that: A. The total number of aliphatic carbon atoms included in R 1 , R 2 , R 3 , R 4 , R 6 and R 7 substituents individually may not exceed six; and B. At least one R 3 or R 5 , substituent includes an oxocarbonyl group, a heterocyclic group or a cyano group.

Claim 23

A composition according to claim 18 wherein n is 1.

Claim 24

A composition according to claim 18 wherein n is 2.

Claim 25

A composition according to claim 18 wherein R 1 is methyl.

Claim 26

A composition according to claim 18 wherein R 2 is alkyl.

Claim 27

A composition according to claim 18 wherein R 2 is methyl.

Claim 28

A composition according to claim 18 wherein R 3 and R 4 are alkyl.

Claim 29

A composition according to claim 18 wherein R 3 and R 4 are phenyl.

Claim 30

A composition according to claim 18 wherein R 4 is isopropyl.

Claim 31

A composition according to claim 18 wherein R 3 is methyl.

Claim 32

A composition according to claim 18 wherein R 5 is naphthyl, benzofuranyl, phenyl or substituted phenyl.

Claim 33

A composition according to claim 18 wherein R 6 and R 7 are individually hydrogen, cyano, alkyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl or cyanoalkylthio.

Claim 34

A composition according to claim 18 wherein A is a divalent aliphatic chain completing a 1,4-dithiane, 1,3-dithiolane, 1,4-thiazine-3one, 1,4-oxazine-3-one, 1,3,5-trithiane, 1,3,5-oxadithiane, 1,4-oxathiane, 1,3-oxathiolane, 1,3-thiazolidin-4-one, or thiophane ring wherein sulfur may be in any of its oxidation states or in any combination thereof.

Claim 35

A composition according to claim 18 wherein the active toxicant is 2-[[0-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentane-sulfenyl) carbamoyl]oximino]]-1,4-dithiane.

Claim 36

A composition according to claim 18 wherein the active toxicant is 7-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl) carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran.

Claim 39

A method according to claim 33 wherein n is 1.

Claim 40

A method according to claim 33 wherein n is 2.

Claim 41

A method according to claim 33 wherein R 1 is methyl.

Claim 42

A method according to claim 33 wherein R 2 is alkyl.

Claim 43

A method according to claim 33 wherein R 2 is methyl.

Claim 44

A method according to claim 33 wherein R 3 and R 4 are alkyl.

Claim 45

A method according to claim 33 wherein R 3 and R 4 are phenyl.

Claim 46

A method according to claim 33 wherein R 4 is isopropyl.

Claim 47

A method according to claim 33 wherein R 3 is methyl.

Claim 48

A method according to claim 33 wherein R 5 is naphthyl, benzofuranyl, phenyl or substituted phenyl.

Claim 49

A method according to claim 33 wherein R 6 and R 7 are individually hydrogen, cyano, alkyl, alkylthio, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, cyanoalkyl, nitroalkyl or cyanoalkylthio.

Claim 50

A method according to claim 33 wherein A is a divalent aliphatic chain completing a 1,4-dithiane, 1,3-dithiolane, 1,4-thiazine-3-one, 1,4-oxazine-3-one, 1,3,5-trithiane, 1,3,5-oxadithiane, 1,4-oxathiane, 1,3-oxathiolane, 1,3-thiazolidin-4-one, or thiophene ring wherein sulfur may be in any of its oxidation states or in any combination thereof.

Claim 51

A method according to claim 33 wherein the compound is 2-[[0-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentanesulfenyl)carbamoyl]oximino]]-1,4-dithiane.

Claim 52

A method according to claim 33 wherein the compound is 7-[N-Methyl-N-(2,4-dimethyl-3-oxo-2-pentane-sulfenyl) carbamoyloxy]-2,2-dimethyl-2,3-dihydrobenzofuran.