Patent EA-004601-B1 (EA)
Title: 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole
Inventor: BAUMANN ERNST
IPC: A01N43/80
Filed: 2000-12-19
Abstract: 1. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of the formula (I) wherein the substituents have the following meanings: R<1>, R<2> represent hydrogen, nitro, halogen, cyano, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6halogenalkoxy, C1-C6alkylthio, C1-C6halogenalkylthio, C1-C6alkylsulfinyl, C1-C6halogenalkylsulfinyl, C1-C6alkylsulfonyl or C1-C6halogenalkylsulfonyl; R<3> represents hydrogen, halogen or C1-C6alkyl; R<4> represents hydrogen or C1-C4alkyl; R<5>, R<6> represent hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4alkoxy-C1-C4-alkyl, di-(C1-C4alkoxy)-C1-C4-alkyl, di-(C1-C4alkyl)-amino-C1-C4-alkyl, di-(C1-C4alkyl)-aminoimino-C1-C4-alkyl, hydroxyimino-C1-C4alkyl, C1-C6alkoxyimino-C1-C4alkyl, C1-C4alkoxycarbonyl-C1-C4alkyl, C1-C4alkylthio-C1-C4alkyl, C1-C4halogenalkyl, C1-C4cyanoalkyl, C3-C8cycloalkyl, C1-C4-alkoxy, C1-C4alkoxy-C2-C4alkoxy, C1-C4halogenalkoxy, C1-C4alkylthio, C1-C4halogenalkylthio, di-(C1-C4)alkylamino, COR<8>, phenyl or benzyl, wherein the latter both substituents can be partially or completely halogenated and/or can have from one to three following groups: nitro, cyano, C1-C4alkyl, C1-C4halogenalkyl, C1-C4alkoxy or C1-C4halogenalkoxy; or R<5>, R<6> represent together C2-C6alkandiyl chain, which can be substituted from one to four times by C1-C4alkyl and/or can be interrupted by oxygen or by optionally substituted C1-C4alkyl nitrogen; R<7> represents halogen, cyano, hydroxy, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6halogenalkoxy, C1-C6alkylthio, C1-C6halogenalkylthio, C1-C6alkylsulfinyl, C1-C6halogenalkylsulfinyl, C1-C6alkylsulfonyl, C1-C6halogenalkylsulfonyl, amino, C1-C6alkylamino, di-(C1-C6alkyl)amino, di-(C1-C4alkoxy)methyl, hydroximino-C1-C4alkyl, C1-C6alkoxyimino-C1-C4alkyl or COR<8>; R<8> represents hydrogen, C1-C4alkyl, C1-C4halogenalkyl, Hydroxy, C1-C4alkoxy, C1-C4alkoxy- C2-C4alkoxy, C1-C4halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkinyloxy or NR<9>R<10>; R<9> represents hydrogen or C1-C4alkyl; R<10> represents C1-C4alkyl; R<11> represents pyrazole that is bound in the 4 position of formula II wherein R<12> represents hydrogen, C1-C4alkyl, C1-C4halogenalkyl, C3-C4alkenyl, C3-C4alkinyl, C1-C4alkylcarbonyl, C1-C4halogenalkylcarbonyl, C1-C4alkylsulfonyl, C1-C4halogenalkylsulfonyl, thienylmethyl, phenyl, benzyl, phenylcarbonyl, phenylsulfonyl or phenylcarbonyl-methyl, wherein phenyl moiety of the latter five substituents can be partially or completely halogenated and/or can have from one to three following groups: nitro, cyano, C1-C4alkyl, C1-C4halogenalkyl, C1-C4alkoxy or C1-C4halogenalkoxy; R<13> represents C1-C6alkyl, C1-C6halogenalkyl or C3-C6cycloalkyl; R<14> represents hydrogen, C1-C6alkyl or C3-C6cycloalkyl; and also the agriculturally useful salts thereof. 2. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claim 1, wherein R<3> represents hydrogen. 3. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claim 1 or 2, wherein R<1>, R<2> represent hydrogen, nitro, halogen, cyano, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6halogenalkoxy, C1-C6alkylthio, C1-C6halogenalkylthio, C1-C6alkylsulfinyl, C1-C6halogenalkylsulfinyl, C1-C6alkylsulfonyl or C1-C6halogenalkylsulfonyl; 4. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of the formula (I) according to claims 1-3, wherein R<12> represents C1-C4alkylsulfonyl, C1-C4halogensulfonyl or phenylsulfonyl, wherein phenyl moiety of the latter five substituents can be partially or completely halogenated and/or can have from one to three following groups: nitro, cyano, C1-C4alkyl, C1-C4halogenalkyl, C1-C4alkoxy or C1-C4halogenalkoxy. 5. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claims 1-3, wherein R<12> represents benzyl, wherein phenyl moiety of the latter five substituents can be partially or completely halogenated and/or can have from one to three following groups: nitro, cyano, C1-C4alkyl, C1-C4halogenalkyl, C1-C4alkoxy or C1-C4halogenalkoxy. 6. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claims 1-3, wherein R<12> represents hydrogen. 7. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claims 1-6, wherein R<5> represents hydrogen, halogen, cyano, nitro, C1-C4alkyl, C1-C4alkoxy-C1-C4-alkyl, C1-C4alkoxycarbonyl-C1-C4-alkyl, C1-C4alkylthio-C1-C4-alkyl, C1-C4halogenalkyl, C1-C4cyanoalkyl, C3-C8cycloalkyl, C1-C4alkoxy, C1-C4alkoxy-C2-C4-alkoxy, C1-C4halogenalkoxy, C1-C4alkylthio, C1-C4halogenalkylthio, di-(C1-C4alkyl)amino, COR<8>, phenyl or benzyl, wherein the latter both substituents can be partially or completely halogenated and/or can have from one to three following groups: nitro, cyano, C1-C4alkyl, C1-C4halogenalkyl, C1-C4alkoxy or C1-C4halogenalkoxy; R<6> represents hydrogen or C1-C4alkyl. 8. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (I) according to claims 1-7, wherein R<5> and R<6> represent hydrogen. 9. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of the formula (I) according to claim 1, wherein pyrazole of formula II, wherein R<12> = H, and substituents R<13> and R<14> have meanings as defined in claim 1, is acidified with activated carboxylic acid IIIalpha or with carboxylic acid IIIbeta, wherein the substituents R<1> to R<7> have the meanings as defined in claim 1, and L<1> represents nucleophil displaced, leaving group, and the acylation product, optionally in the presence of a catalyst, is subjected to regrouping to yield compounds of formula I (where R<12> = H) and, if necessary, for producing 3-(4,5-dihydroisoxazol-5-yl)-benzoylpyrazole of formula I where R<12> is not hydrogen, is subjected to reacting with a compound of formula V, wherein R<12> has the meaning as defined in claim 1, except hydrogen and L<2> represents nucleophil displaced, leaving group. 10. 3-(4,5-dihydroisoxazole-5-yl)benzoylpyrazole of formula (III), wherein R<15> represents hydroxy or hydrolyzing moiety and the substituents from R<1> to R<7> have the meanings as defined in claims 1-8. 11. 3-(4,5-dihydroisoxazol-5-yl)-benzoylpyrazole of formula III according to claim 10, wherein R<15> represents halogen, hydroxy or C1-C6alkoxy. 12. A compound of formula VI wherein L<4> represents halogen and the substituents R<1> to R<7> have the meanings as defined in claim 1. 13. A compound of formula VII wherein the substituents R<1> to R<7> have the meanings as defined in claim 1. 14. A product comprising herbicide active amount of at least one 3-(4,5-Dihydroisoxazol-5-yl)-benzoylpyrazole of formula I or one of the agriculturally useful salts of a compound according to claims 1-8 and usual agents in compositions for plants protection. 15. A method for preparing an agent according to claim 14, wherein herbicide active amount of at least one 3-(4,5-Dihydroisoxazol-5-yl)-benzoylpyrazole of formula I or one of the agriculturally useful salts of a compound according to claims 1-8 is mixed with usual agents in compositions for plants protection. 16. A method of combatting undesirable plant growth, wherein herbicide active amount of at least one 3-(4,5-Dihydroisoxazol-5-yl)-benzoylpyrazole of formula I or one of the agriculturally useful salts of a compound according to claims 1-8 is applied on plants, their locus and/or their seeds. 17. Use of 3-(4,5-Dihydroisoxazol-5-yl)-benzoylpyrazole of formula I or one of the agriculturally useful salts according to claims 1-8 as herbicides.