1,2-Alkylene-4-substituted urazole herbicides

Claim 2

1,2-Alkylene-4-substituted urazole derivatives represented by the formula ##STR149## wherein A represents alkylene or alkenylene containing 3-6 carbon atoms, and wherein the adjacent nitrogen atoms of the urazole radical are bonded to different carbons of the A group, X and Y represent oxygen of sulfur respectively, but when A is alkenylene both X and Y are sulfur, R represents phenyl substituted in the 3- or 4- position with one or two substituents selected from halogen, lower alkyl, lower alkoxy, nitro halogenated benzyloxy or trihalomethyl.

Claim 3

1,2-Alkylene-4-substituted urazole compounds represented by formula ##STR150## wherein A represents alkylene or alkenylene containing 3-6 carbon atoms, and wherein the adjacent nitrogen atoms of the urazole radical are bonded to different carbons of the A group, X and Y represent oxygen or sulfur, respectively, but when A is alkenylene both X and Y are sulfur, Z 1 represents hydrogen, halogen, lower alkyl or trihalomethyl, and Z 2 represents hydrogen, halogen, lower alkyl, lower alkoxy, nitro or halogenated benzyloxy; provided that Z 1 and Z 2 are not both hydrogen.

Claim 4

1,2-Alkylene-4-substituted urazole compounds represented by formula ##STR150## wherein A represents alkylene or alkenylene containing 3-6 carbon atoms, and wherein the adjacent nitrogen atoms of the urazole radical are bonded to different carbons of the A group, X and Y represent oxygen or sulfur, respectively, but when A is alkenylene both X and Y are sulfur, Z 1 represents hydrogen, halogen, lower alkyl or trihalomethyl, and Z 2 represents hydrogen, halogen, lower alkyl, lower alkoxy, nitro or halogenated benzyloxy; provided that Z 1 and Z 2 are not both hydrogen.

Claim 5

A compound of the formula ##STR151## wherein A represents alkylene having 2-8 carbon atoms which may have at least one methyl group and wherein the adjacent nitrogen atoms of urazole radical are bonded to different carbons of the A group, and R represents phenyl having at least one substituent selected from halogen, lower alkyl having 1-4 carbon atoms, lower alkoxy having 1-4 carbon atoms, nitro, monochlorobenzyloxy, or trifluoromethyl; or naphthyl; or a compound of the formula ##STR152## wherein A' represents alkylene having 2-8 carbon atoms, or butenylene which may have at least one methyl group as a side chain and wherein the adjacent nitrogen atoms of the urazole radical are bonded to different carbons of the A' group, Y represents oxygen or sulfur, but when A' is butenylene Y is sulfur, and R' represents phenyl which is substituted with up to three halogens, lower alkyl having 1-4 carbon atoms, lower alkoxy having 1-4 carbon atoms, nitro, halogenated benzyloxy or trihalomethyl; or napthyl.

Claim 6

A compound of the formula ##STR151## wherein A represents alkylene having 2-8 carbon atoms which may have at least one methyl group and wherein the adjacent nitrogen atoms of urazole radical are bonded to different carbons of the A group, and R represents phenyl having at least one substituent selected from halogen, lower alkyl having 1-4 carbon atoms, lower alkoxy having 1-4 carbon atoms, nitro, monochlorobenzyloxy, or trifluoromethyl; or naphthyl; or a compound of the formula ##STR152## wherein A' represents alkylene having 2-8 carbon atoms, or butenylene which may have at least one methyl group as a side chain and wherein the adjacent nitrogen atoms of the urazole radical are bonded to different carbons of the A' group, Y represents oxygen or sulfur, but when A' is butenylene Y is sulfur, and R' represents phenyl which is substituted with up to three halogens, lower alkyl having 1-4 carbon atoms, lower alkoxy having 1-4 carbon atoms, nitro, halogenated benzyloxy or trihalomethyl; or napthyl.

Claim 7

A herbicidal composition consisting essentially of an effective amount of a compound of claims 1, 2 or 3 in combination with an inert agricultural adjuvant.

Claim 8

1,2-Alkylene-4-substituted urazole compounds according to claim 2, wherein Z 1 represents hydrogen, methyl or halogen and Z 2 represents halogen or halogenated benzyloxy.

Claim 9

1,2-Alkylene-4-substituted urazole compounds according to claim 2, wherein Z 1 represents hydrogen, methyl or halogen, Z 2 represents halogen or halogenated benzyloxy, X represents sulfur and Y represents oxygen or sulfur.

Claim 10

1,2-Alkylene-4-substituted urazole compounds according to claim 2, wherein Z 1 represents hydrogen, methyl or halogen, Z 2 represents halogen or halogenated benzyloxy, X and Y represent oxygen.

Claim 11

1,2-Alkylene-4-substituted urazole compounds according to claim 1, wherein A represents alkylene or alkenylene containing 3-5 carbon atoms, Z 2 represents halogen or halogenated benzyloxy and Z 1 represents hydrogen, methyl or halogen.

Claim 12

1,2-Alkylene-4-substituted urazole compounds according to claim 2, wherein A represents tetramethylene or 2-butenylene, Z 1 represents hydrogen, methyl or halogen and Z 2 represent halogen or halogenated benzyloxy.

Claim 13

1,2-Alkylene-4-substituted compounds according to claim 1 or 2, wherein A represents tetramethylene or 2-butenylene group.

Claim 14

1,2-Alkylene-4-substituted compounds according to claims 1 or 2, wherein both X and Y represent oxygen.

Claim 15

1,2-Alkylene-4-substituted compounds according to claim 1 or 2, wherein X represents sulfur and Y represents oxygen or sulfur.

Claim 16

1,2-Tetramethylene-4-(4'-chlorophenyl)urazole.

Claim 17

1,2-Tetramethylene-4-(4'-chlorophenyl)urazole.

Claim 18

1,2-Tetramethylene-4-(4'-bromophenyl)urazole.

Claim 19

1,2-Tetramethylene-4-(4'-bromophenyl)urazole.

Claim 20

1,2-Tetramethylene-4-(4'-iodophenyl)urazole.

Claim 21

1,2-Tetramethylene-4-(4'-iodophenyl)urazole.

Claim 22

1,2-Tetramethylene-4-(4'-fluorophenyl)urazole.

Claim 23

1,2-Tetramethylene-4-(4'-fluorophenyl)urazole.

Claim 24

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl) urazole.

Claim 25

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl) urazole.

Claim 26

1,2-Tetramethylene-4-(4'-chlorophenyl)monothiourazole.

Claim 27

1,2-Tetramethylene-4-(4'-chlorophenyl)monothiourazole.

Claim 28

1,2-Tetramethylene-4-(4'-bromophenyl)monothiourazole.

Claim 29

1,2-Tetramethylene-4-(4'-bromophenyl)monothiourazole.

Claim 30

1,2-Tetramethylene-4-(4'-iodophenyl)monothiourazole.

Claim 31

1,2-Tetramethylene-4-(4'-iodophenyl)monothiourazole.

Claim 32

1,2-Tetramethylene-4-(4'-fluorophenyl)monothiourazole.

Claim 33

1,2-Tetramethylene-4-(4'-fluorophenyl)monothiourazole.

Claim 34

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl)-monothiourazole.

Claim 35

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl)-monothiourazole.

Claim 36

1,2-Tetramethylene-4(4'-chlorophenyl)dithiourazole.

Claim 37

1,2-Tetramethylene-4(4'-chlorophenyl)dithiourazole.

Claim 38

1,2-Tetramethylene-4(4'-bromophenyl)dithiourazole.

Claim 39

1,2-Tetramethylene-4(4'-bromophenyl)dithiourazole.

Claim 40

1,2-Tetramethylene-4(4'-iodophenyl)dithiourazole.

Claim 41

1,2-Tetramethylene-4(4'-iodophenyl)dithiourazole.

Claim 42

1,2-Tetramethylene-4(4'-fluorophenyl)dithiourazole.

Claim 43

1,2-Tetramethylene-4(4'-fluorophenyl)dithiourazole.

Claim 44

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl)dithiourazole.

Claim 45

1,2-Tetramethylene-4-(4'-(4"-chlorobenzyloxy)phenyl)dithiourazole.

Claim 46

1,2-Trimethylene-4-(3,5-dichlorophenyl)urazole.

Claim 47

1,2-Trimethylene-4-(3,5-dichlorophenyl)urazole.

Claim 48

1,2-Tetramethylene-4-(3,5-dichlorophenyl)urazole.

Claim 49

1,2-Tetramethylene-4-(3,5-dichlorophenyl)urazole.