Substituted 2-phenyl-3(2H)-pyridazinones

Details Substituted 2-phenyl-3(2H)-pyridazinones Substituted 2-phenyl-3(2H)-pyridazinones

2000-03-16

2001-05-01

Shah, Mukund J. (Department: 1611)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C544S240000

Reexamination Certificate

active

06225313

ABSTRACT:

The present invention relates to novel substituted 2-phenyl-3(2H)-pyridazinones of the formula I
where:
n is 0, 1 or 2;
R
1
is C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
2
is hydrogen or halogen;
R
3
is halogen or cyano;
R
4
is hydrogen, nitro, cyano, formyl, hydroxylamino, C
1
-C
4
-alkyl, C
1
-C
4
-haloalkyl, —OR
5
, —CH═N—OR
6
, —CH═C(R
7
)—CO—OR
8
, —CO—OR
9
, (C
1
-C
6
-alkylsulfonyl)amino, di(C
1
-C
6
-alkylsulfonyl)amino or
where
R
5
is C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkenyloxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkynyloxy)carbonyl-C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl,
R
6
is hydrogen, C
1
-C
4
-alkyl, hydroxycarbonyl-C
1
-C
4
-alkyl or (C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl,
R
7
is hydrogen, halogen or C
1
-C
4
-alkyl,
R
8
is hydrogen or C
1
-C
6
-alkyl,
R
9
is hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkoxy, hydroxycarbonyl-C
1
-C
4
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkenyloxy)carbonyl-C
1
-C
4
-alkyl, (C
3
-C
6
-alkynyloxy)carbonyl-C
1
-C
4
-alkyl or C
1
-C
4
-alkoxy-(C
1
-C
4
-alkoxy)carbonyl-C
1
-C
4
-alkyl and
R
10
is hydrogen, C
1
-C
6
-alkyl, hydroxycarbonyl or (C
1
-C
6
-alkoxy)carbonyl,
and the agriculturally useful salts of the compounds I.
Furthermore, the invention relates to
the use of the compounds I as herbicides or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation/defoliation of plants which comprise the compounds I as active ingredients,
methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I,
processes for preparing the compound I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I.
Certain phenylpyridazinones, whose general formula—if the substituents are chosen appropriately—includes formally some of the present compounds I, have already been disclosed as herbicidally active compounds in WO 96/39392.
WO 97/07104 relates, inter alia, to 2-phenyl-5-haloalkyl-pyridazin-3-ones, to which a herbicidal action is likewise ascribed. Unlike the present compounds I, however, they do not have an amino group in the 4-position nor a sulfur bridge in the 5-position of the pyridazinone ring.
The herbicidal properties of the prior art compounds are not always entirely satisfactory.
It is an object of the present invention to provide novel phenylpyridazinones having improved herbicidal properties which allow even more selective control of the undesirable plants. It is a further object to provide novel compounds which have desiccant/defoliant action.
We have found that these objects are achieved by the substituted 2-phenyl-3(2H)-pyridazinones of the formula I defined at the outset. Furthermore, we have found herbicidal compositions which comprise the compounds I and which have very good herbicidal activity. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Furthermore, we have found that the compounds I are also suitable for the desiccation and/or defoliation of parts of plants, suitable plants being crop plants such as cotton, potatoes, rapeseed, sunflower, soybean or field beans, in particular cotton. In this regard, we have found compositions for the desiccation and/or defoliation of plants, processes for preparing these compositions and methods for the desiccation and/or defoliation of plants using the compounds I.
Depending on the substitution pattern, the compounds of the formula I can contain one or more chiral centers, in which case they exist in the form of enantiomer or diastereomer mixtures. In the case of compounds I having at least one olefinic radical, E/Z isomers may also be possible. This invention provides both the pure enantiomers or diastereomers and mixtures thereof.
The substituted 2-phenyl-3(2H)-pyridazinones I may be present in the form of their agriculturally useful salts, the kind of salt usually not being important. In general, the salts of those bases and those acid addition salts are suitable which do not adversely affect the herbicidal activity in comparison with the free compound I.
Suitable basic salts are in particular those of the alkali metals, preferably the sodium and potassium salts, those of the alkaline earth metals, preferably calcium salts and magnesium salts, those of the transition metals, preferably zinc salts and iron salts, and ammonium salts, where the ammonium ion may, if desired, carry one to four C
1
-C
4
-alkyl, hydroxy-C
1
-C
4
-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium and trimethyl-(2-hydroxyethyl)-ammonium salts, furthermore phosphonium salts, sulfonium salts such as, preferably, tri-(C
1
-C
4
-alkyl)sulfonium salts, and sulfoxonium salts such as, preferably, tri-(C
1
-C
4
-alkyl)sulfoxonium salts.
Suitable acid addition salts are primarily the hydrochlorides and hydrobromides, sulfates, nitrates, phosphates, oxalates or dodecylbenzenesulfonates.
The organic moieties mentioned in the definition of the substituents R
1
and R
4
to R
10
are—like the term halogen—collective terms for individual listings of the individual group members. All hydrocarbon chains, ie. all the alkyl, haloalkyl, hydroxycarbonylalkyl, alkoxy, alkenyl, alkenyloxy, alkynyl and alkynyloxy moieties can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms. The term halogen represents in each case fluorine, chlorine, bromine or iodine.


REFERENCES:
patent: 2223094 (1996-05-01), None
patent: 2223094 (1996-12-01), None
patent: 95/06641 (1995-03-01), None
patent: 96/39392 (1996-12-01), None
patent: 97/07104 (1997-02-01), None
patent: 98/07700 (1998-02-01), None
patent: 98/07720 (1998-02-01), None
Chem.Pharm.Bll. 21(2) (241-247) (1973)Maki et al.
Takaya et al., vol. 98 (1978)Studies on Pyridazinone Derivatives . . . with translation.
Takaya, M. et al, Yakugaku Zasshi, vol. 98, 1978, 1530-1535, with English Translation.

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