N-substituted perhydrodiazine

Details N-substituted perhydrodiazine N-substituted perhydrodiazine

2001-12-17

2003-10-28

Ford, John M. (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S068000, C540S598000

Reexamination Certificate

active

06639070

ABSTRACT:

The present invention relates to 1-oxa- and 1-thia-3,4-diazines which are substituted in the 4-position, to a process for their preparation and to their use in a process for preparing novel herbicidally active compounds.
WO 94/10173 discloses perhydrogenated 1-oxa-3,4-diazines of the formula A in which Z is S, O, S═O or SO
2
and Q is a C
6
-C
14
-aromatic radical. The compounds A are used as starting materials for preparing herbicides with triazoline-2,5-dione structure (Compounds B).
The compounds of the formula A for their part are prepared by cyclization of substituted N-(N′-arylcarbamoyl)hydrazinoethanols or -thiols with formaldehyde under acidic reaction conditions. The yields of such cyclization reactions are not satisfactory.
In another invention, which is the subject of a parallel application, it has surprisingly been found that compounds of the formula A′
in which Z, X and Q are as defined above and R is a radical which is different from hydrogen have herbicidal activity. Such compounds should be preparable from perhydro-1-oxa- or perhydro-1-thia-3,4-diazines which are substituted in the 4-position at the nitrogen. It was an object of the present invention to provide oxa- and thiadiazines which are substituted in the 4-position at the nitrogen.
We have found that this object is achieved by a process which allows the preparation of 1-oxa- and 1-thia-3,4-diazines which are substituted in the 4-position at the nitrogen in good yields if the substituent located in the 4-position has the meanings given below for R.
Thus, the present invention relates to N-substituted perhydro-3,4-diazines of the formula I
in which the variables Z, R, m and R
A
are as defined below:
Z is O, S, S═O or SO
2
;
R
A
is hydroxyl, CO
2
R
1
, halogen, cyano, C(O)NR
1
2
, OR
2
, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, COR
1
, S(O)
n
R
1
where n=0, 1 or 2, or C(O)SR
1
;
R is CO
2
H, CHO, CN, C(O)OR
3
, C(S)OR
3
, C(O)SR
3
, C(S)SR
3
, C(O)NR
4
R
5
, C(S)NR
4
R
5
, C(O)NHCO
2
R
6
, C(O)NHSO
2
R
6
, C(O)NHSO
3
R
6
, C(O)R
2
, P(O)R
1
OR
1
, P(O)(OR
1
)
2
, S(O)
n
R
2
where n=0, 1, or 2 or SO
2
NHR
1
;
m has the value 0, 1, 2 or 3
and in which the variables R
1
to R
7
are as defined below:
R
1
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
3
-alkoxy-C
1
-C
3
-alkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl;
R
2
is C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, hydroxycarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfinyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfonyl-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkynyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-thioalkyl, C
3
-C
6
-alkenylthio-C
1
-C
6
-alkyl, C
3
-C
6
-alkynylthio-C
1
-C
6
-alkyl, cyano-C
1
-C
6
-alkyl, C
3
-C
6
-halocycloalkyl-C
1
-C
6
-alkyl, halo-C
2
-C
6
-alkenyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-haloalkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-alkylthio-C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkoxy-C
3
-C
6
-alkynyl, C
1
-C
6
-alkylthio-C
3
-C
6
-alkynyl, C
1
-C
6
-alkylcarbonyl, CHR
1
COR
7
, CHR
1
P(O)(OR
7
)
2
, P(O)(OR
7
)
2
, CHR
1
P(S)(OR
7
)
2
, CHR
1
C(O)NR
4
R
5
, CHR
1
C(O)NH
2
,
is phenyl, pyridyl, benzyl, phenoxy-C
1
-C
6
-alkyl, benzyloxy-C
1
-C
6
-alkyl, where the phenyl or pyridyl groups of the five last-mentioned substituents may be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkyl,
R
3
is C
1
-C
15
-alkyl, C
3
-C
8
-cycloalkyl, C
2
-C
10
-alkenyl, C
3
-C
10
-alkynyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkylthio-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfinyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkylsulfonyl-C
1
-C
6
-alkyl, C
1
-C
3
-alkoxy-C
1
-C
3
-alkoxy-C
1
-C
3
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-alkyl, carboxyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
2
-C
6
-alkenyl, C
3
-C
6
-alkenyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxycarbonyl-C
1
-C
6
-alkyl, C
3
-C
8
-cycloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-alkynyloxy-C
1
-C
6
-alkyl, C
1
-C
6
-haloalkoxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkenyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-haloalkynyloxy-C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl-C
1
-C
6
-thioalkyl, C
3
-C
6
-alkenylthio-C
1
-C
6
-alkyl, C
3
-C
6
-alkynylthio-C
1
-C
6
-alkyl, cyano-C
1
-C
6
-alkyl, C
3
-C
6
-halocycloalkyl-C
1
-C
6
-alkyl, halo-C
3
-C
6
-alkenyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-haloalkoxy-C
3
-C
6
-alkenyl, C
1
-C
6
-alkylthio-C
3
-C
6
-alkenyl, C
3
-C
6
-haloalkynyl, C
1
-C
6
-alkoxy-C
3
-C
6
-alkynyl, C
1
-C
6
-haloalkoxy-C
3
-C
6
-alkynyl, C
1
-C
6
-alkylthio-C
3
-C
6
-alkynyl,
is CHR
1
COR
7
, CHR
1
P(O)(OR
7
)
2
, P(O)(OR
7
)
2
, CHR
1
P(S)(OR
7
)
2
,CHR
1
C(O)NR
4
R
5
, CHR
1
C(O)NH
2
, phenoxy-C
1
-C
6
-alkyl, benzyloxy-C
1
-C
6
-alkyl, where the phenyl groups of the two last-mentioned substituents may be substituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy or C
1
-C
4
-haloalkyl; is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzthiazolyl, benzyl, where the 14 last-mentioned substituents may carry, in adjacent positions, a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, or may in each case be mono- to pentasubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, amino, C
1
-C
4
-monoalkylamino, C
1
-C
4
-dialkylamino, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano;
R
4
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy;
R
5
, R
6
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-cycloalkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, C
1
-C
6
-alkoxycarbonyl-C
1
-C
6
-alkyl,
are C
1
-C
6
-alkoxycarbonyl-C
2
-C
6
-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals,
are benzyl which, in adjacent positions of the phenyl ring, may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, or which may be mono- to pentasubstituted by halogen, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkylthio, C
3
-C
6
-cycloalkyl, C
1
-C
4
-alkoxycarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, hydroxyl, nitro or cyano, or
R
4
and R
5
together with the nitrogen atom to which they are attached are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, may, if desired, contain one of the following members: —O—, —S—, —N═, —NH— or N—(C
1
-C
6
-alkyl)—;
R
7
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
3
-alkoxy-C
1
-C
3
-alkyl, C
2
-C
6
-cyanoalkyl, C
3
-C
6
-alkenyl or C
3
-C
6
-alkynyl.
The organic molecule moieties mentioned in the definition of R, R
A
, R
1
to R
7
and at phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, i.e. all (unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties can be straight-chain or branched.
Halogenated substituents preferably carry one, two, three, four or five identical or different halogen atoms or are perhalogenated.
The term halogen denotes in eac

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