3-nitroisoxazoles and their use in the protection of materials
AssigneeBayer Aktiengesellschaft
InventorsHermann Uhr, Oliver Kretschik, Martin Kugler, Peter Wachtler
Life of this patent
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Abstract
The 3-nitroisoxazoles of the formula (I) 1 in which R1 and R2 are each as defined in the description, some of which are known, are highly suitable for use as biocides for protecting industrial materials.
Claims12
A method comprising treating a microbe or a habitat of the microbe with a compound and allowing the compound to act on the microbe or its habitat, wherein the compound is of formula (I):
- 9
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl.
A microbicidal composition comprising:
- (A) a compound of the formula (I)
- 10
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl,
- (B) solvents or diluents and,
- (C) optionally processing auxiliaries, or active compounds, or mixtures thereof.
A process for preparing a microbicidal composition comprising:
- (A) a compound of the formula (I)
- 11
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl,
- (B) solvents or diluents and,
- (C) optionally processing auxiliaries, or active compounds, or mixtures thereof,
- the process comprising
- mixing (i) a compound of the formula (I)
- 12
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl,
- with (ii) solvents or (iii) diluents and, optionally (iii) with processing auxiliaries, active compounds, or mixtures thereof.
An industrial material comprising a compound of the formula
- 13
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl.
A compound of the formula (I)
- 14
- wherein
- R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano or represent in each case optionally substituted alkyl, alkenyl, alkinyl or aryl, except for
- methyl 3-nitro-isoxazole-5-carboxylate (CAS-RN:
- 40995-06-0)
- ethyl 3-nitro-isoxazole-5-carboxylate (Beilstein RN:
- 6598833)
- 3-nitro-5-phenylisoxazole (CAS-RN:
- 6455-30-7)
- 3-nitro-5-methylisoxazole (CAS-RN:
- 750097-82-2)
- 3-(3-nitro-isoxazol-5-yl)-prop-2-yn-1-ol (Beilstein RN:
- 1106231)
- 3,5-dinitro-isoxazole (CAS-RN:
- 42216-62-6)
- 4-methyl-3,5-dinitro-isoxazole (CAS-RN:
- 42216-63-7)
- 3-nitro-5-(3-nitro-prop-1-ynyl)-isoxazole (Beilstein RN:
- 1119643)
- 3-nitroisoxazole (CAS-RN:
- 39485-31-9)
- 4-chloromethyl-3-nitro-isoxazole (Beilstein RN:
- 6594348)
- 4-methyl-3-nitro-isoxazole (Beilstein RN:
- 6593345)
- 5-butyl-3-nitro-isoxazole (CAS-RN:
- 40995-04-8)
- 3-nitro-5-hydroxymethyl-isoxazole (CAS-RN:
- 75079-83-3)
- 5-(bromo-prop-1-ynyl)-3-nitro-isoxazole (CAS-RN:
- 40995-02-6)
- 3-nitro-1-phenyl-isoxazole (Beilstein RN:
- 6596756)
- (3-nitro-isoxazol-4-yl)-phenyl-methanone (Beilstein RN:
- 6599593)
- 4-(4-methoxy-phenyl)-3-nitro-isoxazole (Beilstein RN:
- 6600205)
- 3-nitro-4-(2-nitro-phenyl)-isoxazole (Beilstein RN:
- 6604179)
- 3-nitro-4-(4-nitrophenyl)-isoxazole (Beilstein RN:
- 6604546)
- 3-nitro-4-(2,4-dinitrophenyl)-isoxazole (Beilstein RN:
- 6612177)
- 3-nitro-isoxazole-5-carbaldehyde (CAS-RN:
- 108802-81-9)
- 3-nitro-5-acetyl-isoxazole (CAS-RN:
- 54468-91-6).
A process for preparing a compound of the formula (I)
- 15
- wherein R1 and R2 independently of one another each represent hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl,
- the process comprising reacting (i) a compound of the formula (II)
- R2—C≡C—R1 (II)
- wherein R1 and R2 are each as defined above with (ii) tetranitroethylene, optionally in the presence of a diluent.
A process for preparing a compound of the formula (I)
- 16
- wherein
- R1 is hydrogen, halogen, nitro, cyano, or represent in each case an optionally substituted alkyl, alkenyl, alkinyl or aryl,
- R2 represents hydrogen,
- the process comprising reacting (i) a compound of the general formula (III)
- X—CH2—C≡C—R1 (III)
- in which
- R1 is as defined above and
- X represents a leaving group, preferably bromine, iodine, chlorine, tosylate or mesylate
- with (ii) metal nitrites, optionally, in the presence of diluents.
Dependencies are inferred from the claim text.