Herbicidal hydroximic acid derivatives

Details Herbicidal hydroximic acid derivatives Herbicidal hydroximic acid derivatives

1999-09-21

2002-05-14

Ford, John M. (Department: 1674)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C544S311000, C558S003000, C558S007000

Reexamination Certificate

active

06387849

ABSTRACT:

This application was filed on Sep. 21,1999, as a national phase application of International Application No. PCT/EP 98/01,440, filed Mar. 12, 1998.
The present invention relates to novel substituted hydroximic acid derivatives of the formula I
where X and the substituents R
1
to R
7
have the following meanings:
X is oxygen or sulfur;
Y is oxygen or sulfur;
R
1
is hydrogen, C
1
-C
4
-alkyl, amino, C
1
-C
4
-alkylamino or di(C
1
-C
4
-alkyl)amino;
R
2
is C
1
-C
3
-haloalkyl;
R
3
is hydrogen, halogen or C
1
-C
4
-alkyl;
R
4
is hydrogen or halogen;
R
5
is cyano or halogen;
R
6
is C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl or phenyl-C
1
-C
6
-alkyl, it being possible for the phenyl ring to be unsubstituted or to have attached to it one to three substituents each selected from the group consisting of cyano, nitro, halogen, C
1
-C
4
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy, C
2
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy and (C
1
-C
6
-alkoxy) carbonyl;
R
7
is a C
1
-C
6
-alkyl, C
2
-C
6
-alkenyl, C
3
-C
6
-alkynyl or phenyl-C
1
-C
6
-alkyl group, it being possible for these 4 groups to be unsubstituted or to have attached to them one or two substituents each selected from the group consisting of halogen, C
1
-C
3
-alkoxy, C
1
-C
3
-alkoxyimino, (C
1
-C
3
-alkoxy)carbonyl, (C
1
-C
3
-alkylamino)carbonyl, di(C
1
-C
3
-alkyl)aminocarbonyl and CO—N(C
1
-C
3
-alkyl)-(C
1
-C
3
-alkoxy), it being possible for the 4 last-mentioned radicals, in turn, to have attached to them a (C
1
-C
3
-alkoxy)carbonyl or C
1
-C
4
-alkoxy group;
and the agriculturally useful salts of the compounds I.
Furthermore, the invention relates to
the use of the compounds I as herbicides and/or for the desiccation/defoliation of plants,
herbicidal compositions and compositions for the desiccation/defoliation of plants which comprise compounds I as active substances,
processes for preparing the compounds I and herbicidal compositions and compositions for the desiccation/defoliation of plants using the compounds I,
methods for controlling undesirable vegetation and for the desiccation/defoliation of plants using the compounds I, and
novel intermediates of the formula VII.
EP-A 408 382 disclosess herbicidally active hydroximic acid derivatives of the formula
where R
n
is hydrogen, hydroxymethyl or C
1
-C
3
-[halo]alkyl, R
o
is hydrogen, nitro, halogen, C
1
-C
6
-[halo]alkyl or hydroxymethyl, R
p
is nitro, cyano or halogen, R
q
is hydrogen, C
1
-C
3
-alkyl, -alkoxy or -alkoxy-C
1
-C
2
-alkyl and R
r
is hydrogen, C
1
-C
4
-alkyl, C
2
-C
3
-haloalkyl, C
3
-C
6
-cycloalkyl, phenyl or benzyl.
DE-A 44 24 791 discloses certain hydroximic acids of cinnamic acid.
It is an object of the present invention to provide novel hydroximic acid derivatives which have a good herbicidal action. The object also extends to providing novel compounds which act as desiccants/defoliants.
We have found that this object is achieved in accordance with the invention by the hydroximic acid derivatives of the formula I. preferred compounds of the formula I can be seen from the sub-claims and from the description which follows.
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. This invention provides both the pure enantiomers or diasteromers and mixtures thereof.
Agriculturally useful salts are in particular the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the herbicidal activity of the compounds I. Suitable cations are therefore in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which may carry one to four C
1
-C
4
-alkyl substituents, and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri(C
1
-C
4
-alkyl)sulfonium and sulfoxonium ions, preferably tri(C
1
-C
4
-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, hydrogencarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic moieties mentioned for the substituents R
1
to R
3
, R
6
, R
7
or as radicals on phenyl rings are collective terms for individual enumerations of each of the group members, as is the meaning halogen. All carbon chains, ie. all alkyl, haloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylamino and phenylalkyl moieties can be straight-chain or branched.
Halogenated substituents preferably have attached to them one to five identical or different halogen atoms.
Examples of individual meanings are:
halogen: fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine;
C
1
-C
4
-alkyl; CH
3
, C
2
H
5
, CH
2
-C
2
H
5
, CH(CH
3
)
2
, n-C
4
H
9
, CH(CH
3
)—C
2
H
5
, CH
2
—CH(CH
3
)
2
or C(CH
3
)
3
;
C
1
-C
6
-alkyl and the alkyl moiety of C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably C
1
-C
4
-alkyl, in particular methyl or ethyl;
C
1
-C
6
-haloalkyl: C
1
-C
6
-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, eg. CH
2
F, CHF
2
, CF
3
, CH
2
Cl, CH(Cl)
2
, C(Cl)
3
, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, C
2
F
5
, 3-fluoropropyl, 3-chloropropyl or CF
2
-C
2
F
5
, preferably C
1
-C
4
-haloalkyl, in particular trifluoromethyl or 1,2-dichloroethyl;
C
2
-C
6
-alkenyl: ethenyl, prop-1-en-1-yl, prop-2-en-1-yl, 1-methylethenyl, n-buten-1-yl, n-buten-2-yl, n-buten-3-yl, 1-methylprop-1-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, n-penten-1-yl, n-penten-2-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-1-en-1-yl, 2-methylbut-1-en-1-yl, 3-methylbut-1-en-1-yl, 1-methybut-2-en-1-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, 1,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-1-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-1-en-2-yl, 1-ethylprop-2-en-1-yl, n-hex-1-en-1-yl, n-hex-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, 1-methylpent-1-en-1-yl, 2-methylpent-1-en-1-yl, 3-methylpent-1-en-1-yl, 4-methylpent-1-en-1-yl, 1-methylpent-2-en-1-yl, 2-methylpent-2-en-1-yl, 3-methylpent-2-en-1-yl, 4-methylpent-2-en-1-yl, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-1-en-1-yl, 1,2-dimethylbut-2-en-1-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-1-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-1-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-1-en-1-yl, 3,3-dimethylbut-2-en-1-yl, 1-ethylbut--en-1-yl, 1-ethylbut-2-en-1-yl, 1-ethy

Affiliated with

Also associated with

Rating

Herbicidal hydroximic acid derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Herbicidal hydroximic acid derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Herbicidal hydroximic acid derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2893244