3,5-Dioxo-1,2,4-triazines

Claim 2

A herbicidal composition which comprises as an active ingredient at least one of the 3,5-dioxo-1,2,4-triazine derivatives of the formula: ##STR142## wherein (1) (a) --X--Y-- represents --N═CH--, (b) R 1 is a hydrogen atom, a hydroxylmethyl group, an aminomethyl group of the formula: ##STR143## (in which R 3 and R 4 are each hydrogen, C 1 -C 12 alkyl, allyl, propargyl, cyanoethyl, phenyl or C 3 -C 10 cycloalkyl or, when taken together with the adjacent nitrogen atom, represent a 3 to 13-membered saturated nitrogen-containing heterocyclic group optionally containing an oxygen atom or an additional nitrogen atom and/or optionally bearing not more than three methyl or ethyl groups), an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.5 (in which R 5 is C 1 -C 9 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl or cyclohexyl, these R 5 groups being optionally substituted with not more than five halogen, C 1 -C 5 alkoxy, phenyl or phenoxy groups, or phenyl, naphthyl, nicotinyl or isonicotinyl, these being optionally substituted with not more than five methyl, methoxy, halogen, nitro or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR144## (in which Z is --CH 2 CH 2 -- and m is an integer of 1 or 2 or Z is --CHX'CH 2 --, --CHX'CHX'-- or --CH═CH-- (X' being halogen) and m is 1) and (c) R 2 is a hydrogen atom, an aminomethyl group of the formula: ##STR145## (in which R 3 and R 4 are each as defined above) or a cyclic ether group of the formula: ##STR146## (in which Z' is --CH 2 CH 2 -- and n is an integer of 1 or 2 or Z is --CHY'CH 2 -- (Y' being halogen) and n is 1), provided that when R 2 is a hydrogen atom, R 1 is a hydroxymethyl group, an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.5 or a cyclic ether group of the formula: ##STR147## when R 2 is an aminomethyl group of the formula: ##STR148## R 1 is an aminomethyl group of the formula: ##STR149## or when R 2 is a cyclic ether group of the formula: ##STR150## R 1 is a hydrogen atom or a group of the formula: ##STR151## or (2) (a) --X--Y-- represents --NH--CH 2 --, (b) R 1 is a hydrogen atom, an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.6 (in which R 6 is C 1 -C 9 alkyl, cyclohexyl or phenyl, these being optionally substituted with not more than five methyl, methoxy, fluorine, chlorine or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR152## (in which p is an integer of 3 or 4) and (c) R 2 is a hydrogen atom or a cyclic ether group of the formula: ##STR153## (in which p is as defined above), provided that when R 2 is a cyclic ether group of the formula: ##STR154## R 1 is a hydrogen atom or a cyclic ether group of the formula: ##STR155## in the free or salt form in a herbicidally effective amount, and at least one inert carrier or diluent.

Claim 3

The composition according to claim 1, wherein the active ingredient is representable by the formula (I) wherein --X--Y-- is --N═CH--, R 1 is ##STR156## and R 2 is ##STR157## (in which R 3 and R 4 are each as defined in claim 1).

Claim 4

The composition according to claim 1, wherein the active ingredient is representable by the formula (I) wherein --X--Y-- is --N═CH-- and R 1 is --CH 2 --OOC--R 5 (in which R 5 is as defined in claim 1).

Claim 5

The composition according to claim 1, wherein the active ingredient is representable by the formula (I) wherein --X--Y-- is --N═CH--, R 1 is --H or ##STR158## and R 2 is --H or ##STR159## (in which Z, Z', m and n are each as defined in claim 1).

Claim 6

The composition according to claim 1, wherein the active ingredient is 2-hydroxymethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine or a salt thereof.

Claim 7

The composition according to claim 1, wherein the active ingredient is 3,5-dioxo-hexahydro-1,2,4-triazine or a salt thereof.

Claim 8

The composition according to claim 1, wherein the active ingredient is 2,4-bis(N-n-butyl-N-methylaminomethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 9

The composition according to claim 1, wherein the active ingredient is 2,4-bis(N,N-dimethylaminomethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 10

The composition according to claim 1, wherein the active ingredient is 2-(3-methylbenzoyloxymethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine or a salt thereof.

Claim 11

The composition according to claim 1, wherein the active ingredient is 3,5-dioxo-4-(tetrahydro-2-furanyl)-2,3,4,5-tetrahydro-1,2,4-triazine or a salt thereof.

Claim 12

A method for exterminating wild oats, which comprises applying a herbicidally effective amount of at least one of the 3,5-dioxo-1,2,4-triazine derivatives as defined in claim 1 in the free or salt form to the area where it is desired to exterminate or control the wild oats.

Claim 13

The method according to claim 11, wherein the area of application is a field where wheat is cultivated.

Claim 14

A 3,5-dioxo-1,2,4-triazine derivative of the formula: ##STR160## wherein (1) (a) --X--Y-- represents --N═CH--, (b) R 1 is a hydrogen atom, a hydroxylmethyl group, an aminomethyl group of the formula: ##STR161## (in which R 3 and R 4 are each hydrogen, C 1 -C 12 alkyl, allyl, propargyl, cyanoethyl, phenyl or C 3 -C 10 cycloalkyl or, when taken together with the adjacent nitrogen atom, represent a 3 to 13-membered saturated nitrogen-containing heterocyclic group optionally containing an oxygen atom or an additional nitrogen atom and/or optionally bearing not more than three methyl or ethyl groups), an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.5 (in which R 5 is C 1 -C 9 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl or cyclohexyl, these R 5 groups being optionally substituted with not more than five halogen, C 1 -C 5 alkoxy, phenyl or phenoxy groups, or phenyl, naphthyl, nicotinyl or isonicotinyl, these being optionally substituted with not more than five methyl, methoxy, halogen, nitro or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR162## (in which Z is --CH 2 CH 2 -- and m is an integer of 1 or 2 or Z is --CHX'CH 2 --, --CHX'CHX'-- or --CH═CH-- (X' being halogen) and m is 1) and (c) R 2 is a hydrogen atom, an aminomethyl group of the formula: ##STR163## (in which R 3 and R 4 are each as defined above) or a cyclic ether group of the formula: ##STR164## (in which Z' is --CH 2 CH 2 -- and n is an integer of 1 or 2 or Z is --CHY'CH 2 -- (Y' being halogen) and n is 1), provided that when R 2 is a hydrogen atom, R 1 is a hydroxymethyl group, an acyloxymethyl group of the formula: --CH.sub.2 OOC--R.sup.5 or a cyclic ether group of the formula: ##STR165## when R 2 is an aminomethyl group of the formula: ##STR166## R 1 is an aminomethyl group of the formula: ##STR167## or when R 2 is a cyclic ether group of the formula: ##STR168## R 1 is a hydrogen atom or a group of the formula: ##STR169## or (2) (a) --X--Y-- represents --NH--CH 2 --, (b) R 1 is a hydrogen atom, an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.6 (in which R 6 is C 1 -C 9 alkyl, cyclohexyl or phenyl, these being optionally substituted with not more than five methyl, methoxy, fluorine, chlorine or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR170## (in which p is an integer of 3 or 4) and (c) R 2 is a hydrogen atom or a cyclic ether group of the formula: ##STR171## (in which p is as defined above), provided that when R 2 is a cyclic ether group of the formula: ##STR172## R 1 is a hydrogen atom or a cyclic ether of the formula: ##STR173## except the following cases: (a) --X--Y-- is --N═CH--, R 1 is hydroxymethyl and R 2 is a potassium atom; (b) --X--Y-- is --N═CH--, R 1 is hydroxymethyl and R 2 is a hydrogen atom; (c) --X--Y-- is --N═CH--, R 1 is ##STR174## and R 2 is ##STR175## (d) --X--Y-- is --N═CH--, R 1 is --CH 2 --OOC--CH 3 and R 2 is a hydrogen atom; (e) --X--Y-- is --N═CH--, R 1 is ##STR176## and R 2 is a hydrogen atom; and (f) --X--Y-- is --NH--CH 2 --, R 1 is a hydrogen atom and R 2 is a hydrogen atom, or a salt thereof.

Claim 15

A 3,5-dioxo-1,2,4-triazine derivative of the formula: ##STR160## wherein (1) (a) --X--Y-- represents --N═CH--, (b) R 1 is a hydrogen atom, a hydroxylmethyl group, an aminomethyl group of the formula: ##STR161## (in which R 3 and R 4 are each hydrogen, C 1 -C 12 alkyl, allyl, propargyl, cyanoethyl, phenyl or C 3 -C 10 cycloalkyl or, when taken together with the adjacent nitrogen atom, represent a 3 to 13-membered saturated nitrogen-containing heterocyclic group optionally containing an oxygen atom or an additional nitrogen atom and/or optionally bearing not more than three methyl or ethyl groups), an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.5 (in which R 5 is C 1 -C 9 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl or cyclohexyl, these R 5 groups being optionally substituted with not more than five halogen, C 1 -C 5 alkoxy, phenyl or phenoxy groups, or phenyl, naphthyl, nicotinyl or isonicotinyl, these being optionally substituted with not more than five methyl, methoxy, halogen, nitro or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR162## (in which Z is --CH 2 CH 2 -- and m is an integer of 1 or 2 or Z is --CHX'CH 2 --, --CHX'CHX'-- or --CH═CH-- (X' being halogen) and m is 1) and (c) R 2 is a hydrogen atom, an aminomethyl group of the formula: ##STR163## (in which R 3 and R 4 are each as defined above) or a cyclic ether group of the formula: ##STR164## (in which Z' is --CH 2 CH 2 -- and n is an integer of 1 or 2 or Z is --CHY'CH 2 -- (Y' being halogen) and n is 1), provided that when R 2 is a hydrogen atom, R 1 is a hydroxymethyl group, an acyloxymethyl group of the formula: --CH.sub.2 OOC--R.sup.5 or a cyclic ether group of the formula: ##STR165## when R 2 is an aminomethyl group of the formula: ##STR166## R 1 is an aminomethyl group of the formula: ##STR167## or when R 2 is a cyclic ether group of the formula: ##STR168## R 1 is a hydrogen atom or a group of the formula: ##STR169## or (2) (a) --X--Y-- represents --NH--CH 2 --, (b) R 1 is a hydrogen atom, an acyloxymethyl group of the formula: --CH.sub.2 --OOC--R.sup.6 (in which R 6 is C 1 -C 9 alkyl, cyclohexyl or phenyl, these being optionally substituted with not more than five methyl, methoxy, fluorine, chlorine or trihalomethyl groups or with 3,4-methylenedioxy) or a cyclic ether group of the formula: ##STR170## (in which p is an integer of 3 or 4) and (c) R 2 is a hydrogen atom or a cyclic ether group of the formula: ##STR171## (in which p is as defined above), provided that when R 2 is a cyclic ether group of the formula: ##STR172## R 1 is a hydrogen atom or a cyclic ether of the formula: ##STR173## except the following cases: (a) --X--Y-- is --N═CH--, R 1 is hydroxymethyl and R 2 is a potassium atom; (b) --X--Y-- is --N═CH--, R 1 is hydroxymethyl and R 2 is a hydrogen atom; (c) --X--Y-- is --N═CH--, R 1 is ##STR174## and R 2 is ##STR175## (d) --X--Y-- is --N═CH--, R 1 is --CH 2 --OOC--CH 3 and R 2 is a hydrogen atom; (e) --X--Y-- is --N═CH--, R 1 is ##STR176## and R 2 is a hydrogen atom; and (f) --X--Y-- is --NH--CH 2 --, R 1 is a hydrogen atom and R 2 is a hydrogen atom, or a salt thereof.

Claim 16

The 3,5-dioxo-1,2,4-triazine derivative according to claim 13, wherein --X--Y-- is --N═CH--, R 1 is ##STR177## and R 2 is ##STR178## (in which R 3 and R 4 are each as defined in claim 11).

Claim 17

The 3,5-dioxo-1,2,4-triazine derivative according to claim 13, wherein --X--Y-- is --N═CH-- and R 1 is --CH 2 --OOC--R 5 (in which R 5 is as defined in claim 11).

Claim 18

The 3,5-dioxo-1,2,4-triazine derivative according to claim 13, wherein --X--Y-- is --N═CH--, R 1 is --H or ##STR179## and R 2 is --H or ##STR180## (in which Z, Z', m and n are each as defined in claim 11).

Claim 19

The 3,5-dioxo-1,2,4-triazine derivative 2,4-bis(N-n-butyl-N-methylaminomethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 20

The 3,5-dioxo-1,2,4-triazine derivative 2,4-bis(N-n-butyl-N-methylaminomethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 21

The 3,5-dioxo-1,2,4-triazine derivative 2,4-bis(N,N-dimethylaminomethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 22

The 3,5-dioxo-1,2,4-triazine derivative 2,4-bis(N,N-dimethylaminomethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine.

Claim 23

The 3,5-dioxo-1,2,4-triazine derivative 2-(3-methylbenzoyloxymethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine, or a salt thereof.

Claim 24

The 3,5-dioxo-1,2,4-triazine derivative 2-(3-methylbenzoyloxymethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine, or a salt thereof.

Claim 25

The 3,5-dioxo-1,2,4-triazine derivative 3,5-dioxo-4-(tetrahydro-2-furanyl)-2,3,4,5-tetrahydro-1,2,4-triazine, or a salt thereof.

Claim 26

The 3,5-dioxo-1,2,4-triazine derivative 3,5-dioxo-4-(tetrahydro-2-furanyl)-2,3,4,5-tetrahydro-1,2,4-triazine, or a salt thereof.