Phenylpyridazinones

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

Reexamination Certificate

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C544S239000, C544S240000, C544S241000

Reexamination Certificate

active

06551963

ABSTRACT:

This application is a 371 of PCT/EP96/02246, which was filed on May 24, 1996.
The invention relates to novel phenylpyridazinones, to processes for their preparation, to their use as herbicides and to novel intermediates and to processes for their preparation.
It is known that certain substituted phenylpyridazinones such as, for example, the compounds 5-amino-4-chloro-2-phenyl-pyridazin-3-one and 4-bromo-5-methyl-2-phenyl-pyridazin-3-one have herbicidal properties (cf. DE 1105232 and DE 2706700; cf. also DE 1670309, DE 1670315, DE 1695840, DE 2526643, DE 2808193, DE 2821809 and U.S. Pat. No. 5,298,502). However, the herbicidal activity of these compounds is not in all respects satisfactory.
This invention, accordingly, provides the novel substituted phenylpyridazinones of the general formula (I)
in which
R
1
represents halogen,
R
2
represents cyano, carbamoyl, thiocarbamoyl, halogen or represents respectively optionally halogen-substituted alkyl, alkoxy or alkylthio,
R
3
represents the grouping —A
1
—A
2
—A
3
 in which
A
1
represents a single bond, represents oxygen, sulphur, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
— where A
4
represents hydrogen, hydroxyl, alkyl, alkenyl, alkinyl, alkoxy, aryl, alkylsulphonyl or aryl-sulphonyl,
A
1
furthermore represents respectively optionally halogen-substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A
2
represents a single bond, represents oxygen, sulphur, —SO—, —SO
2
—, —CO— or the grouping —N—A
4
— where A
4
represents hydrogen, hydroxyl, alkyl, alkoxy, aryl, alkylsulphonyl or arylsulphonyl,
A
2
furthermore represents respectively optionally halogen-substituted alkanediyl, alkenediyl, azaalkenediyl, alkinediyl, cycloalkanediyl, cycloalkenediyl or phenylene,
A
3
represents hydrogen with the proviso that in this case A
1
and/or A
2
do not represent a single bond,
A
3
furthermore represents hydroxyl, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulpho, chlorosulphonyl, halogen,
A
3
furthermore represents respectively optionally halogen- or alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy(thio)phosphoryl,
A
3
furthermore represents respectively optionally halogen-substituted alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxy-carbonyl, alkinyl, alkinyloxy, alkinylamino or alkinyloxycarbonyl, represents respectively optionally halogen-, cyano-, carboxy-, alkyl- and/or alkoxy-carbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl,
A
3
furthermore represents respectively optionally nitro-, cyano-, carboxy-, halogen-, alkyl-, halogenoalkyl-, alkyloxy-, halogenoalkyloxy- and/or alkoxy-carbonyl-substituted aryl, aryloxy, aralkyl, arylalkoxy, aryloxycarbonyl or arylalkoxycarbonyl,
A
3
furthermore represents respectively optionally fully or partially hydrogenated pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylalkyl, furylalkyl, thienylalkyl, oxazolylalkyl, isoxazolalkyl, thiazolalkyl, pyridinylalkyl, pyrimidinylalkyl, pyrazolylalkoxy, furylalkoxy, perhydropyranylalkoxy or pyridylalkoxy, or
R
2
and R
3
together represent one of the groupings below —Q
1
—CQ
2
—, —Q
1
—CQ
2
—Q
3
—, —Q
1
—C(R
7
,R
8
)—Q
3
—, —C(R
7
,R
8
)—CQ
2
—, —C(R
7
,R
8
)—Q
1
—CQ
2
—, —Q
1
—C(R
7
,R
8
)—C(R
7
,R
8
)—, —Q
1
—C(R
7
,R
8
)—C(R
7
,R
8
)—Q
3
—, —C(R
7
,R
8
)—C(R
7
,R
8
)—CQ
2
—, —Q
1
—C(R
7
)═C(R
7
)—, —C(R
7
)═C(R
7
)—CQ
2
—, —Q
1
—C(R
7
,R
8
)—CQ
2
—, —N(R
9
)—C(R
7
;R
8
)—CQ
2
—, —C(R
7
)═N—, —Q
1
—CQ
2
—C(R
7
,R
8
)—, —Q
1
—CQ
2
—N(R
9
)—, —Q
1
—C(R
7
,R
8
)—CQ
2
—N(R
9
)—, —C(R
7
,R
8
)—Q
1
—CQ
2
—N(R
9
)—, —C(R
7
,R
8
)—C(R
7
,R
8
)—N(R
9
)—, —C(R
7
,R
8
)—C(R
7
,R
8
)—CQ
2
—N(R
9
)—, —C(R
7
)═C(R
7
)—N(R
9
)—, —C(R
7
)═C(R
7
)—CQ
2
—N(R
9
)—, —C(R
7
,R
8
)—CQ
2
—N(R
9
)—, —N(R
9
)—C(R
7
;R
8
)—CQ
2
—N(R
9
)—, —C(R
7
)═N—N(R
9
)—, —Q
1
—CQ
2
—C(R
7
,R
8
)—N(R
9
)—, Q
1
—C(R
7
,R
8
)—C(R
7
,R
8
)—CQ
2
—N(R
9
)—
 where
Q
1
, Q
2
and Q
3
are identical or different and each represents oxygen or sulphur,
R
7
and R
8
are identical or different and each on its own represents hydrogen, halogen or alkyl, or together they represent alkanediyl, and
R
9
represents hydrogen, hydroxyl, represents optionally cyano-, halogen-, alkoxy-, alkyl-carbonyl- or alkoxy-carbonyl-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl,
R
9
furthermore represents respectively optionally halogen-substituted alkenyl or alkinyl,
R
9
furthermore represents respectively optionally halogen- or alkyl-substituted cycloalkyl or cycloalkylalkyl, represents respectively optionally halogen-substituted alkoxy or alkenyloxy, or
R
9
furthermore represents respectively optionally cyano-, halogen- alkyl-, halogenoalkyl-, alkoxy- or halogenoalkoxy-substituted arylalkyl or arylalkoxy, and
R
4
, R
5
and R
6
are identical or different and each represents hydrogen, cyano, thiocarbamoyl, nitro, hydroxyl, mercapto, amino, halogen or represents respectively optionally halogen-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino,
except for the prior art compounds 2-(2,4,5-trichloro-phenyl)-pyridazin-3-one (cf. Liebigs. Ann. Chem. 697 (1966), 42-61) and 4-chloro-5-dimethylamino-2-(4-chloro-2-fluoro-5-propargyloxy-phenyl)-pyridazin-3-one (cf. U.S. Pat No. 5,298,502), which are excluded by disclaimer.
The novel substituted phenylpyridazinones of the general formula (I) are obtained when
(a) halogenoarenes of the general formula (II)
 in which
R
1
, R
2
and R
3
are each as defined above and
X
1
represents halogen
are reacted with pyridazinones of the general formula (III)
 in which
R
4
, R
5
and R
6
are each as defined above—or with acid adducts or alkali metal salts of compounds of the formula (III)—if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(b) aryihydrazines of the general formula (IV)
 in which
R
1
, R
2
and R
3
are each as defined above are reacted with &bgr;-trihalomethyl-enones of the general formula (V)
 in which
R
4
, R
5
and R
6
are each as defined above and
X
2
represents halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or
(c) hydrazonecarboxylic acids of the general formula (VI)
 in which
R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are each as defined above are cyclocondensed, i.e. reacted with a dehydrating agent, or
(d) 2,4-disubstituted phenylpyridazinones of the general formula (Ia)
 in which
R
1
, R
2
, R
4
, R
5
and R
6
are each as defined above are nitrated, i.e. reacted with a nitrating agent.
The compounds of the general formula (I) can also be converted into other compounds of the general formula (I) according to the definition above by further customary methods, for example by nucleophilic substitution (for example R
3
: F→OH, SH, NH
2
, OCH
3
, NHSO
2
CH
3
; R5: Cl→N(CH
3
)
2
) or by further functional group conversions (for example R
2
: CONH
2
→CN, CN→CSNH
2
; R
3
: NO
2
→NH
2
, NH
2
→F, Cl, Br, CN, NHSO
2
CH
3
, SO
2
Cl)—cf. also the Preparation Examples.
The novel substituted phenylpyridazinones of the general formula (I) have strong herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably provides compounds of the formula (I) in which
R
1
represents fluorine, chlorine or bromine,
R
2
represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents respective

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