# US 6,297,195 B1 · Substituted triazoloazine sulphonamides

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- Number: US 6,297,195 B1
- Document ID: US6297195B1
- Status: Granted
- Kind: B1
- Application number: 09/214,773
- Filed: 1999-05-10
- Granted: 2001-10-02
- Earliest claimed: 1996-07-19
- Assignees: Bayer Aktiengesellschaft
- Inventors: Ernst Rudolf F. Gesing; Mark Wilhelm Drewes; Johannes R. Jansen; Rolf Kirsten; Joachim Kluth; Klaus-Helmut Müller; Ulrich Philipp; Hans-Jochem Riebel; Otto Schallner; Detlef Wollweber; Markus Dollinger; Klaus Stenzel; Christoph Erdelen
- Web page: https://patentgrep.com/patent/US6297195B1

## CPC

- C07D 487/04: Ortho-condensed systems
- A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS

## Abstract

The invention concerns novel substituted triazoloazine sulphonamides of formula (I) in which Q1 stands for nitrogen or a CH group: Q2 stands for nitrogen or a CH group; R1 stands for hydrogen or halogen, or for C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino or di(C1-C4 alkyl)amino, in each case optionally substituted by hydroxy, halogen or C1-C4 alkoxy; R2 stands for hydrogen or halogen, or for C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylamino or di(C1-C4 alkyl)amino, in each case optionally substituted by halogen; and Ar stands for 4-cyano-2,5-difluoro-phenyl, 2,6-dimethoxy-phenyl, 2-bromo-3-trifluoro-methyl-phenyl, 2-bromo-5-trifluoromethyl-phenyl, 6-chloro-pyridine-3-yl-methyl or one of the 5- or 6-member (hetero)cyclic groups mentioned in the description. The invention also concerns salts of these substances, a process for preparing the novel compounds, and their use as plant-treatment agents.

## Claims

### Claim 1

A substituted triazoloazinesulphonamide of the formula (I)
wherein
Q1 represents a CH grouping,
Q2 represents nitrogen,
R1 represents halogen or represents C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino or di-(C1-C4- alkyl)amino, each of which is unsubstituted or substituted by hydroxyl, halogen or C1-C4-alkoxy,
R2 represents hydrogen, halogen or represents C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylamino or di-(C1-C4-alkyl)amino, each of which is unsubstituted or substituted by halogen, and
Ar represents
wherein
A13 represents cyano, carbamoyl, 5,6-dihydro-1,4,2-dioxazin-3-yl, halogen, C1-C4-alkyl, C1-C4-alkyl-carbonyl or C1-C4-alkoxy-carbonyl,
A14 represents hydrogen, represents cyano, cabamoyl, halogen, C1-C4-alkyl, C1-C4-alkylcarbonyl or C1-C4-alkoxy-carbonyl,
A15 represents hydrogen, represents cyano, carbamoyl, halogen, C1-C4-alkyl, C1-C4-aklylcarbonyl or C1-C4-alkoxy-carbonyl, or together with A14 represents a fused benzo grouping,
and a salt of the compound of the formula (I), with the following proviso:
i) if A13 represents C1-C4-alkoxy-carbonyl then A14 and A15 cannot both be hydrogen.

### Claim 2 (depends on 1)

A compound the formula (I) according to claim 1, wherein
Q1 represents a CH grouping,
Q2 represents nitrogen,
R1 represents fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethyl-amino or diethylamino, each of which is unsubstituted or substituted by fluorine, chlorine, methoxy or ethoxy,
R2 represents hydrogen, fluorine, chlorine, bromine or represents methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamine, n- or i-propylamino, dimethylamino or diethylamino, each of which is unsubstituted or substituted by fluorine, chlorine, methoxy, or ethoxy,
Ar represents
wherein
A13 represents cyano, carbamoyl, 5,6-dihydro-1,4,2-dioxazin-3-yl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, priopionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
A14 represents hydrogen, represents cyano, carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
A15 represents hydrogen, represents cyano, carbomoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i propoxycarbonyl, or together with A14 represents a fused benzo grouping,
and a salt of the compound of the formula (I) selected from the group consisting of lithium, sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di-(C1-C4-alkyl) ammonium, tri-(C1-C4-alkyl)-ammonium, tetra-(C1-C4-alkyl)-ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium and di-(C1-C2-alkyl)-benzyl-ammonium salts of compounds of the formula (I).

### Claim 3

A substituted triazoloazinesulphonamide of the formula (I)

### Claim 4 (depends on 1)

A plant treatment composition comprising at least one compound of the formula (I) or one of the salts thereof according to claim 1 and one or more members selected from the group consisting of liquid solvents, solid carriers, emulsifiers, dispersing agents and foam-forming agents.

### Claim 5 (depends on 1)

A method for controlling weeds, undesirable microorganisms, arthropods and/or nematodes comprising the step of allowing compounds of the formula (1) or salts thereof according to claim 1 to act on the weeds, the undesirable microorganisms, the arthropods and/or nematodes or their habitat.