Condensed heterocyclic derivative, process for its production and herbicide tool

 

(57) Abstract:

The proposed condensed heterocyclic derivative of the formula I, where R is hydrogen, hydroxyl, C1-C6-alkoxy, optionally substituted C1-C6-alkylcarboxylic, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy,

C1-C6-alkoxycarbonyl C1-C6-alkylcarboxylic, three-C1-C6-alkylsilane-C1-C6-alkoxy, benzyloxy, which may be optionally substituted C1-C6-alkoxy, C2-C6-alkenylamine, the group NR6R7where R6and R7together with the nitrogen atom form imidazolyl, R3and R4may be the same or different, represent a C1-C6-alkoxy, optionally double-substituted with halogen, C1-C6-alkyl, W is oxygen atom or sulfur , Z is a methine group, A possibly substituted 5-or 6-membered heterocyclic ring. Proposed herbicide tool that includes condensed heterocyclic derivative of the formula I, in an effective amount. When processing flooded fields and on the hills and in the processing of leaves compound of formula I is impact on culture. 3 S. and 73 p. F.-ly. 82 table.

see text

1. Condensed heterocyclic derivative of the formula

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where a heterocyclic ring of the formula

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< / BR>
< / BR>
< / BR>
< / BR>
Deputy R is a hydrogen atom, a hydroxyl group, WITH1- C6-alkoxygroup, optionally substituted C1- C6-alkylcarboxylic,1WITH6-alkoxy, C1- C6-alkoxy WITH1WITH6-alkoxy, C1- C6-alkoxycarbonyl1WITH6-alkylcarboxylic, three1WITH6-alkylsilane-C1WITH6-alkoxy, benzyloxy, which may be optionally substituted C1WITH6-alkoxy, C2WITH6-alkenylacyl, the group NR6R7where R6and R7together with the nitrogen atom form imidazolyl, if And when the specified heterocyclic ring And 1, R1a hydrogen atom, a C1WITH6-alkyl, optionally substituted with halogen, phenyl, optionally substituted with halogen;

R2WITH1WITH6-alkoxycarbonyl, optionally substituted with halogen, C1WITH6-alkylthio, cyan, teinila, fullam, phenyl, optionally substituted C1WITH6-alkoxy, C3WITH5-C is genitically, group-CR8NR9; C1- C6-alkylsulphonyl, optionally substituted with halogen, phenylcarbinol, optionally substituted with halogen, cyano, benzyldimethyl; C2WITH6-alkenylacyl, optionally substituted with halogen or1WITH6-alkyl; C2WITH6-alkyloxyaryl, optionally substituted C1WITH6-alkyl, isopropylaminocarbonyl; C1WITH6-alkylthiomethyl, optionally substituted N(C2H5)2group;

R6the atom of hydrogen or C1WITH6-alkyl;

R7WITH1WITH6-alkyl, phenyl, benzyl

or R6and R7together with the nitrogen atom form pyrrolidinyl or piperidinyl;

R8WITH1WITH6-alkyl;

R9WITH1WITH6-alkoxy;

when And said heterocyclic ring a-2, R1- C1WITH6-alkyl, C1WITH6-alkoxy;

R2a hydrogen atom, a C1WITH6-alkyl;

when And said heterocyclic ring a-3, R1is a hydrogen atom, a C1WITH6-alkyl, C1- C6-alkoxycarbonyl;

R2WITH1WITH6-alkyl, C1- C6-aldoxycarb the R2a hydrogen atom, formyl, carboxyl,1- C6-alkoxycarbonyl, optionally substituted with halogen; C2- C6alkenyl,2WITH6-alkenylacyl,1< / BR>
WITH6-alkyl, optionally substituted by cyano, C1- C6-alkylsulphonyl, optionally substituted with halogen, cyano, a nitro-group, a group CH N R9where R9the hydroxy-group, WITH1WITH6-alkoxygroup NR10R11where R10a hydrogen atom, R11WITH1- C6-alkoxycarbonyl, phenylcarbinol; C1- C6-alkoxycarbonylmethyl, phenoxycarbonyl, optionally substituted with halogen;

when And said heterocyclic ring A-5, R1is a hydrogen atom;

when And said heterocyclic ring A-6, R1- C1WITH6-alkyl;

when And said heterocyclic ring A-9, R1is a hydrogen atom;

when And said heterocyclic ring A-11, X1is an oxygen atom, a methylene group, NH group;

X2an oxygen atom, a carbonyl group, CHOH group, a sulfur atom;

Q1methylene group, a carbonyl group,

in the case when the
X2an oxygen atom, a sulfur atom;

Q2carbonyl group, a group of CR18R19where R18a hydrogen atom, and R19the atom of hydrogen or C1WITH6-alkyl;

Q3group C CH2the group CR18R19where R18and R19may be the same or different and represent a hydrogen atom or a C1WITH6-alkyl;

each of the substituents R3and R4that may be the same or different, represent a1WITH6-alkoxy, optionally double-substituted with halogen, C1WITH6-alkyl;

Deputy R5a hydrogen atom, a C1- C6-alkoxy-(C1WITH6)-alkyl; C1- C6-alkylcarboxylic-(C1WITH6)-alkyl; C1- C6-alkylsulphonyl; benzoyl,1WITH6-alkylsulfonyl, tamilselvan, three-(C1WITH6)-alkylsilane group, 4,6-dimethoxypyrimidine;

Deputy W is an oxygen atom or a sulfur atom;

Z methine group.

2. A derivative of pyrimidine under item 1, in which the Deputy And in the formula I represents a-1, a-2, a-3 or a-4.

3. A derivative of pyrimidine under item 1, in which the Deputy And in the formula I represents A-11, A-12.

5. A derivative of pyrimidine under item 1, in which the Deputy And in the formula I represents a-1, a-2, a-3 or a-4, Deputy W is an oxygen atom, and each of the substituents R3and R4WITH1- C6-alkoxygroup.

6. A derivative of pyrimidine under item 1, in which the Deputy And in the formula I represents A-5, A-6, a-9, Deputy W is an oxygen atom, and each of the substituents R3and R4WITH1WITH6-alkoxygroup.

7. A derivative of pyrimidine under item 1, in which the Deputy And in the formula I represents A-11, A-12, Deputy W is an oxygen atom and each of the substituents R3and R4WITH1WITH6-alkoxygroup.

8. A derivative of pyrimidine under item 1, characterized in that it is a

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-isopropoxycarbonyl-2-methylbenzofuran-4-carboxylic acid,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-propoxycarbonyl-2-methylbenzofuran-4-carboxylic acid,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylic acid,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-(2-floratone)-carbonyl-2-methyl - benzo-furan-4-carboxylic acid,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-propargyloxy-carb is souran-4-carboxylic acid,

pivaloyloxymethyl-(4,6-dimethoxypyrimidine-2-yl)oxy-3-propoxycarbonyl-2 methylbenzofuran-4-carboxylate,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-methoxycarbonyl-2-methylindol-4-carboxylic acid,

5-(4,6-dimethoxypyrimidine-2-yl)oxy-2-methylindol-4-carboxylic acid, or

5-(4,6-dimethoxypyrimidine-2-yl)oxy-3-methoxycarbonyl-2-methylbenzofuran-4-carboxylic acid.

9. The method of obtaining the derivative of pyrimidine under item 1, including the interaction of the compounds of formula II

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where the substituents R, A, W take the values defined above,

with the compound of the formula III

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where the Deputy L1halogen atom, a C1- C6-alkylsulfonyl group, benzylaniline group or substituted benzylaniline group;

the substituents R3, R4and Z take values defined above,

in a solvent in the presence of a base.

10. Herbicide agent, comprising the active ingredient and target additives, characterized in that as the active ingredient it contains a compound of General formula I according to any one of paragraphs.1 8 in an effective amount.

Priority signs:

13.07.92 on PP.1, 2, 3, 5, 6, 8, 9 and 10.

14.05.93 on PP.4 and 7.

 

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The invention relates to racemic mixtures and (S)-4-[(2-benzothiazolyl)methylamino]--[(3,4-differience)methyl]-1-piperazineethanol, which can be represented by formula

< / BR>
and its pharmaceutically acceptable acid additive salts (salts of acid incorporation)

The invention relates to new derivatives of sulfamethoxypyrazine and herbicides containing them as active ingredients

The invention relates to new chemical substances, which have valuable pharmacological properties, more particularly to a nitrogen-containing heterocyclic compounds of General formula I

< / BR>
where X is oxygen or sulfur;

Y is carbon or nitrogen;

Z is carbon or nitrogen, and Y and Z are not simultaneously mean nitrogen;

R1and R2independent from each other and denote hydrogen, alkyl with 1 to 6 carbon atoms, halogen, trifluoromethyl, nitrile, alkoxy with 1 to 6 carbon atoms, a group of CO2R7where R7means hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)NR8R9where R8and R9not dependent from each other and denote hydrogen, alkyl with 1 to 3 carbon atoms, methoxy or together with the nitrogen form a morpholine, pyrrolidine or piperidine-NR10R11where R10and R11denote hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)R12where R12means alkyl with 1 to 6 carbon atoms, group-SO2R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has a specified value, and-SO2NR13R14where R13and R142R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has the specified value, -SO2NR13R14where R13and R14have a specified value, a nitrogroup, 1-piperidinyl, 2-, 3 - or 4-pyridine, morpholine, thiomorpholine, pyrrolidine, imidazole, unsubstituted or substituted at the nitrogen by alkyl with 1 to 4 carbon atoms, 2-thiazole, 2-methyl-4-thiazole, dialkylamino with 1 to 4 carbon atoms in each alkyl group, or alkilany ether with 1 to 4 carbon atoms;

R4an ester of formula-CO2R16where R16means alkyl with 1 to 4 carbon atoms, the amide of formula C(O)NR17R18where R17and R18independent from each other and denote hydrogen, alkyl with 1 to 2 carbon atoms, methoxy or together with the nitrogen form a morpholine, piperidine or pyrrolidine, phenyl, unsubstituted or substituted by residues from the group comprising halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, 3-methyl-1,2,4-oxadiazol-5-yl, 2 - or 3-thienyl, 2-, 3 - or 4-pyridyl, 4-pyrazolylborate 4 stands, the ketone of the formula C(O)R19'where R19means alkyl with 1 to 3 carbon atoms, phenyl or 1-Mei-2-yl, a simple ester of the formula-CH2OR20where R20means alkyl with 1 to 3 carbon atoms, thioether formula-CH2SR20where R20has the specified value, the group CH2SO2CH3amines of the formula-CH2N(R20)2where R20has the specified value, the remainder of the formula-CH2NHC(O)R21where R21means methyl, amino or methylamino - group-CH2NHSO2Me2where Me denotes methyl carbamate of the formula CH2OC(O)NHCH3;

R5and R6independent from each other and denote hydrogen or methyl;

n is 0,1 or 2,

Provided that the substituents are not simultaneously have the following meanings: Y and Z is carbon, R1or R2hydrogen, halogen, alkyl with 1 to 4 carbon atoms, alkoxy with 1 to 4 carbon atoms, cyano, nitro, trifluoromethyl, R3unsubstituted phenyl and R4group-C(O)OR16'where R16'means hydrogen, alkyl, alkenyl or quinil, group-C(O)N(R18')(R19'), where R18'and R19'denote hydrogen, alkyl with 1 to 6 carbon atoms, phenyl, alkoxy or together with the nitrogen form pyrrolidine, piperidine or morpholine, cyanotic, unsubstituted phenyl and 4-imidazole,

in the form of a racemate or an individual enantiomers and their salts, are inhibitors of leukotriene biosynthesis

The invention relates to compounds of the formula

(I)

where R1represents hydrogen, lower alkyl, lower alkenyl, lower quinil, aryl lower alkyl, cycloalkyl lower alkyl, lower alkoxy lower alkyl, hydroxy lower alkyl, amino lower alkyl, mono - or di-lower alkyl, amino lower alkyl, formyl, lower alkylsulphonyl, amino lower alkylsulphonyl, lower alkoxycarbonyl, mono - or di-aryl-substituted lower alkyl, arylcarbamoyl lower alkyl, aryloxy lower alkyl, or lower alkylene

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X represents O or S;

W represents hydrogen, halogen, hydroxy, lower alkoxy, aryl lower alkoxy, nitro, trifluoromethyl or

< / BR>
where R3represents hydrogen, lower alkyl or aryl lower alkyl, and R4represents lower alkyl or aryl lower alkyl; or alternatively the groupas a whole represents the

< / BR>
R5is hydrogen, lower alkyl, aryl or aryl lower alkyl; and

Z predepression

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< / BR>
where X is oxygen or sulfur;

Y is carbon or nitrogen;

Z is carbon or nitrogen, and Y and Z are not simultaneously mean nitrogen;

R1and R2independent from each other and denote hydrogen, alkyl with 1 to 6 carbon atoms, halogen, trifluoromethyl, nitrile, alkoxy with 1 to 6 carbon atoms, a group of CO2R7where R7means hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)NR8R9where R8and R9not dependent from each other and denote hydrogen, alkyl with 1 to 3 carbon atoms, methoxy or together with the nitrogen form a morpholine, pyrrolidine or piperidine-NR10R11where R10and R11denote hydrogen or alkyl with 1 to 6 carbon atoms, group-C(O)R12where R12means alkyl with 1 to 6 carbon atoms, group-SO2R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has a specified value, and-SO2NR13R14where R13and R142R12where R12has the specified value, -NHC(O)R12where R12has the specified value, -NHSO2R12where R12has the specified value, -SO2NR13R14where R13and R14have a specified value, a nitrogroup, 1-piperidinyl, 2-, 3 - or 4-pyridine, morpholine, thiomorpholine, pyrrolidine, imidazole, unsubstituted or substituted at the nitrogen by alkyl with 1 to 4 carbon atoms, 2-thiazole, 2-methyl-4-thiazole, dialkylamino with 1 to 4 carbon atoms in each alkyl group, or alkilany ether with 1 to 4 carbon atoms;

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R5and R6independent from each other and denote hydrogen or methyl;

n is 0,1 or 2,

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