Patent EA-003590-B1 (EA)
Title: Substituted (4-brompyrazole-3-yl)benzazoles
Inventor: ZAGAR CYRILL
IPC: C07F9/6541
Filed: 1999-04-22
Abstract: 1. A substituted (4-bromopyrazol-3-yl)benzazole of the formula I where substituent have the following value. R<1> is hydrogen, C1-C4-alkyl or C1-C4-haloalkyl; R<2> is cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl; R<4> is hydrogen or halogen; R<5> is hydrogen, halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy; Z is a group -N=C(XR<6>)-O- or -N=C(XR<6>)-S- which may be attached to a via the nitrogen, oxygen or sulfur; X is a chemical bond, oxygen, sulfur, -S(O)-, -SO<2>-, -NH- or -N(R<7>)-; R<6>, R<7> independently of one another are each C1-C6-alkyl, C1-C6-haloalkyl, cyano- C1-C6-alkyl, hydroxy- C1-C6-alkyl, C3-C6-alkenyl, cyano-C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, cyano- C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy- C1-C4-alkyl, C3-C4-alkenyloxy- C1-C4-alkyl, C3-C4-alkynyloxy- C1-C4-alkyl, C3-C8-cycloalkyloxy- C1-C4-alkyl, amino- C1-C4-alkyl, C1-C4-alkylamino- C1-C4-alkyl, di(C1-C4-alkyl)amino- C1-C4-alkyl, C1-C4-alkylthio- C1-C4-alkyl, C1-C4-haloalkylthio- C1-C4-alkyl, C3-C4-alkenylthio- C1-C4-alkyl, C3-C4-alkynylthio- C1-C4-alkyl, C1-C4-alkyl-sulfinyl- C1-C4-alkyl, C1-C4-haloalkylsulfinyl- C1-C4-alkyl, C3-C4-alkenylsulfinyl- C1-C4-alkyl, C3-C4-alkynyl-sulfinyl- C1-C4-alkyl, C1-C4-alkylsulfonyl- C1-C4-alkyl, C1-C4-haloalkylsulfonyl- C1-C4-alkyl, C3-C4-alkenyl- sulfonyl-C1-C4-alkyl, C3-C4-alkynylsulfonyl- C1-C4-alkyl, hydroxycarbonyl- C1-C4-alkyl, (C1-C4-alkoxy)carbonyl- C1-C4-alkyl, which may carry a cyano or (C1-C4-alkoxy)carbonyl group, (C1-C4-alkylthio)carbonyl- C1-C4-alkyl, aminocarbonyl- C1-C4-alkyl, C1-C4-alkylaminocarbonyl- C1-C4-alkyl, di(C1-C4-alkyl)aminocarbonyl- C1-C4-alkyl, di(C1-C4-alkyl)-phosphonyl- C1-C4-alkyl, (C1-C4-alkoxy)imino- C1-C4-alkyl, (C3-C4-alkenyloxy)imino- C1-C4-alkyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl- C1-C4-alkyl, phenyl, phenyl- C1-C4-alkyl, 3- to 7-membered heterocyclyl or heterocyclyl- C1-C4-alkyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member, and where each cycloalkyl, phenyl and heterocyclyl ring may be unsubstituted or may carry from one to four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy, (C1-C4-haloalkyl)carbonyloxy and di(C1-C4-alkyl)amino; if X is a chemical bond, oxygen, sulfur, -NH- or -N(R<7>)-, R<6> may also be (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkoxy)carbonyl, C1-C4-alkylsulfonyl or C1-C4-haloalkylsulfonyl; if X is a chemical bond, R<6> may furthermore be hydrogen, cyano, mercapto, amino, halogen, -CH2-CH(halogen)-R<8>, -CH=CH-R<8> or -CH=C(halogen)-R<8>, where R<8> is hydroxycarbonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-alkylthio)carbonyl, aminocarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl or di(C1-C4-alkyl)phosphonyl; or R<6> and R<7> together are a 1,3-propylene, tetramethylene, pentamethylene or ethyleneoxyethylene chain which may in each case be unsubstituted or may carry from 1 to 4 C1-C4-alkyl groups or one or two (C1-C4-alkoxy)carbonyl groups, and the agriculturally useful salts of these compounds I. 2. The use of substituted (4-bromopyrazol-3-yl)benzazoles and their agriculturally useful salts, as claimed in claim 1, as herbicides or for the desiccation/defoliation of plants. 3. A herbicidal composition, comprising a herbicidally effective amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally useful salt of I, as claimed in claim 1, and at least one inert liquid and/or solid carrier and also, if desired, at least one surfactant. 4. A composition for the desiccation and/or defoliation of plants, comprising such an amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally useful salt of I, as claimed in claim 1, that it acts as a desiccant and/or defoliant, and at least one inert liquid and/or solid carrier and also, if desired, at least one surfactant. 5. A process for preparing herbicidally active compositions, which comprises mixing a herbicidally effective amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally utilizable salt of I, as claimed in claim 1, with at least one inert liquid and/or solid carrier and also, if desired, at least one surfactant. 6. A process for preparing compositions having desiccant and/or defoliant action, which comprises mixing such an amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally utilizable salt of I, as claimed in claim 1, that it acts as a desiccant/defoliant with at least one inert liquid and/or solid carrier and also, if desired, at least one surfactant. 7. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally useful salt of I, as claimed in claim 1, to act on plants, their habitat or on seeds. 8. A method for the desiccation and/or defoliation of plants, which comprises allowing such an amount of at least one substituted (4-bromopyrazol-3-yl)benzazole of the formula I or an agriculturally utilizable salt of I, as claimed in claim 1, that it acts as a desiccant and/or defoliant to act on plants. 9. The process as claimed in claim 8, wherein cotton is treated. 10. A process for the preparation of substituted (4-bromopyrazol-3-yl)benzazoles of the formula I as claimed in claim 1 in which z is -N=C(R<6>)-O-, which comprises diazotizing an aminophenylpyrazole for the formula IIIa or IIIb, reacting the diazonium salt which is formed with an alkali metal azide to give an azidophenylpyrazole of the formula Va or Vb and finally reacting this with a carboxylic acid of the formula R<6>-COOH. 11. An azidophenylpyrazole of the formula Va or Vb where the substituents R<1>, R<2>, R<4> and R<5> are as each defined in claim 1.