1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production...

Details 1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production... 1-Aryl-1,3,5-triazine-4-thione-2,6-diones, production...

2001-08-15

2003-08-05

Balasubramanian, Venkataraman (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S230000, C544S221000, C544S222000, C540S607000

Reexamination Certificate

active

06602825

ABSTRACT:

The present invention relates to novel 1-aryl-4-thiotriazines of the formula I
in which the variables have the following meanings:
R
1
is hydrogen, amino, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
2
is hydrogen, amino, C
1
-C
4
-alkyl or C
1
-C
4
-haloalkyl;
R
3
is hydrogen or halogen;
R
4
is cyano or halogen;
Y is nitrogen, the methine group or, together with R
5
, is a bridge >C—O—C(R
6
)═N—;
R
5
is
1) hydrogen, hydroxyl, mercapto, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl,
2) C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, C
3
-C
6
-cycloalkoxy, C
3
-C
6
-cycloalkylthio, C
2
-C
6
-alkenyloxy, C
2
-C
6
-alkenylthio, C
2
-C
6
-alkynyloxy or C
2
-C
6
-alkynylthio, it being possible, if desired, for each of these 8 radicals to have attached to it one of the following substituents: halogen, cyano, —CO—R
8
, —CO—OR
8
or —CO—N(R
8
)—R
9
;
3) —COR
11
, —C(R
11
)(OR
13
)(OR
14
), —C(R
11
)═C(R
15
)—CO—R
16
, —CH(R
11
)—CH(R
15
)—CO—R
16
, —CO—OR
20
, —C(R
10
)═N—OR
7
, —N(R
21
)—R
22
or —CO—N(R
21
)—R
22
;
R
6
is hydrogen, halogen, C
1
-C
6
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkenyloxy, C
3
-C
6
-alkynyloxy, C
3
-C
6
-cycloalkyl or C
3
-C
6
-cycloalkoxy, it being possible for each of the last-mentioned 8 radicals, if desired, to have attached to it one to three substituents, in each case selected from the group consisting of halogen, C
1
-C
6
-alkoxy and —CO—OR
8′
;
R
7
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, or benzyl;
R
8
, R
8′
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkyl-C
1
-C
4
-alkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkynyl, C
1
-C
6
-alkoxy-C
1
-C
6
-alkyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl, (C
3
-C
6
-alkenyloxy)carbonyl-C
1
-C
6
-alkyl, phenyl or phenyl-C
1
-C
6
-alkyl, it being possible for the phenyl group and the phenyl ring of the phenyl alkyl group to be unsubstituted or to have attached to them one to three radicals, in each case selected from the group consisting of halogen, nitro, cyano, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and (C
1
-C
6
-alkyl)carbonyl;
R
9
is hydrogen or C
1
-C
6
-alkyl;
R
10
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-alkoxy, it being possible for the 2 last-mentioned radicals to have attached to them one of the following substituents: C
1
-C
6
-alkoxy, (C
1
-C
6
-alkoxy)carbonyl or phenoxycarbonyl;
R
11
is hydrogen, C
1
-C
6
-alkyl or C
1
-C
6
-haloalkyl;
R
13
, R
14
independently of one another are C
1
-C
6
-alkyl or together are a saturated 2- to 4-membered carbon chain which can have attached to it a C
1
-C
6
-alkyl radical;
R
15
is hydrogen, cyano, halogen or C
1
-C
6
-alkyl;
R
16
is O—R
23
or —N(R
21
)R
22
;
R
20
, R
23
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
2
-C
6
-alkenyl or C
2
-C
6
-alkynyl, it being possible for each of the last-mentioned 4 groups to have attached to it one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, (C
1
-C
6
-alkyl)carbonyl, (C
1
-C
6
-alkoxy)carbonyl, (C
1
-C
6
-alkyl)carbonyloxy, (C
3
-C
6
-alkenyloxy)carbonyl, (C
3
-C
6
-alkynyloxy)carbonyl or C
1
-C
6
-alkoxy-(C
1
-C
6
-alkoxy)carbonyl; or C
3
-C
6
-cycloalkyl, phenyl or phenyl-C
1
-C
6
-alkyl, where the phenyl rings can be unsubstituted or, in turn, can have attached to them one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-haloalkyl, C
1
-C
6
-alkoxy and (C
1
-C
6
-alkoxy)carbonyl;
R
21
, R
22
independently of one another are hydrogen, C
1
-C
6
-alkyl, C
3
-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
-alkyl)carbonyl, (C
1
-C
6
-alkoxy)carbonyl, (C
1
-C
6
-alkoxy)carbonyl-C
1
-C
6
-alkyl or C
1
-C
6
-alkylsulfonyl,
or R
21
and R
22
together with the joint nitrogen atom, are a saturated or unsaturated 4- to 7-membered aza heterocycle which, if desired, may contain one of the following members, in addition to carbon ring members: —O—, —S—, —N═, —NH— or —N(C
1
-C
6
-alkyl)—;
and the agriculturally useful salts and enol ethers of the compounds I.
Moreover, the invention relates to
the use of the compounds I as herbicides,
herbicidal compositions which comprise the compounds I as active substances,
processes for the preparation of the compounds I and of herbicidal compositions using the compounds I, and
methods of controlling undesirable vegetation using the compounds I.
DE-A 40 00 624 describes the specifically substituted 1-phenyltriazines as having a fungicidal action. A herbicidal action is not mentioned. Thiotriazines are not mentioned.
EP-A 640 600 describes substituted 4-thiotriazines which have a herbicidal action and which are 4-5-fused in the phenyl substituent.
The subject-matter of EP-A 584 655 and—to a small extent—also WO99/05125 is aryltriazinetriones of the type of the compounds I and their use as herbicides. A multiplicity of aryltriazines and arylthiotriazines fall under the general formulae; however, individual compounds having a thioketone group in the triazine moiety are not mentioned in either publication.
We have found that arylthiotriazines of the formula I as defined above have a particularly good herbicidal action. There have also been found herbicidal compositions which comprise the compounds I and which have a very good herbicidal action. Moreover, there have been found processes for the preparation of these compositions and methods for controlling undesirable vegetation 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 are present as enantiomer or diastereomer mixtures. In the case of compounds I which contain at least one olefinic residue, E/Z isomers may also be possible. Subject-matter of the invention are not only the pure enantiomers or diastereomers but also their mixtures.
Suitable amongst agriculturally useful salts are especially the salts of those cations, or the acid addition salts of those acids, whose cations or anions, respectively, do not adversely affect the herbicidal action of the compounds I. Thus, especially suitable cations are 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 also the ammonium ion which, if desired, can have attached to it one to four C
1
-C
4
-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, moreover 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 mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C
1
-C
4
-alkanoic acids, preferably formate, acetate, propionate and butyrate.
The organic moieties mentioned in the definition of R
1
to R
3
, R
5
to R
23
and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, that is to say all (unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties, can be straight-chain or branched.
Halogenated substituents preferably have attached to them one to five identical or different halogen atoms.
The meaning halogen is in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
C
1
-C
4
-alkyl: CH
3
, C
2
H
5
, n-propyl, CH(CH
3
)
2
, n-butyl, CH(CH
3
)-C
2
H
5
, 2-methylpropyl or C(CH

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