Compounds of the formula I

where

• R¹ is H or alkyl of 1 to 6 carbons or R¹ and R⁸ taken together form a group (CH₂)_v wherein v is 1 to 7;
• R² is
  
  where
• each R⁸ is independently H, OH, C₁ to C₄-O-alkyl or alkyl of 1 to 4 carbons; or an R¹ and an R⁸ taken together form a group (CH₂)_v wherein v is 1 to 7,
• R⁹ is COOR¹; CH₂OH; CHO; tetrazole; NHSO₂R¹⁰ wherein R¹⁰ is OH, alkyl or alkoxy of 1 to 6 carbons, perhaloalkyl of 1 to 6 carbons, phenyl or phenyl substituted by alkyl or alkoxy groups of 1 to 3 carbons, halogen, hydroxy, COOH, CN, formyl or acyl of 1 to 6 carbons; CONHSO₂R¹⁰; hydroxymethylketone; CN; or CON(R⁸)₂;
• X is O; S; SO; S0₂; NR¹¹ wherein R¹¹ is H, alkyl of 1 to 6 carbons, acyl of 1 to 6 carbons, CN; CR¹R⁸;
  
  or the unit wherein the dotted line represents an optical triple bond and in which the R¹ and R⁸ substituents are absent when a triple bond is present;
• r and q are each independently 0 to 5 and p is 0 or 1 provided that the total of p, q and r is 2 to 6;
• R³ is H, alkyl of 1 to 6 carbons; phenyl or phenyl substituted by R⁴; or C₁ to C₄ alkylphenyl or C₁ to C₄ alkylphenyl in which the phenyl is substituted by R⁴;
• R⁴, R⁵, R⁶ and R⁷ are each independently selected from:
  • (1) hydrogen;
  • (2) alkyl having 1 to 6 carbon atoms;
  • (3) alkenyl having 2 to 6 carbon atoms;
  • (4) -(CH₂)_nM
    
    wherein n is 0 to 3 and M is
    • a) OR¹²;
    • b) halogen;
    • c) CF₃;
    • d) SR¹²;
    • e) phenyl or substituted phenyl wherein substituted phenyl is as defined below in the definition of R¹²;
    • ^f) COOR¹³;
    • g)
    • h) tetrazole;
    • i) wherein R¹⁵ is C₁ to C₆ alkyl, benzyl or phenyl;
    • j) -NR¹³R¹³;
    • k) -NHSO₂R¹⁶ wherein R¹⁶ is C₁ to C₆ alkyl, phenyl, or CF₃;
    • I)
    • m) -SOR¹²;
    • n) -CON¹³R¹³;
    • o) -SO₂NR¹³R¹³;
    • p) -SO₂R¹²;
    • q) N0₂;
    • r)
    • s)
    • t)
    • u) CN;
• each R¹² independently is H; C₁ to C₆ alkyl; benzyl; phenyl or substituted phenyl wherein the substituents are C₁ to C₃ alkyl, halogen, CN, CF₃, COOR¹³, CH₂COOR¹³, C₁ to C₃ alkoxy, or C₁ to C₄ perfluoroalkyl;
• each R¹³ is independently H, phenyl or C₁ to C₆ alkyl; and,
• each R¹⁴ independently is H, (CH₂)_nCOOR¹³ wherein n is 0 to 4, C₁ to C₆ alkyl, CF₃, phenyl, or substituted phenyl wherein substituted phenyl is as defined above in the definition of R¹²;

Compounds of the formula I

where

• R¹ is H or alkyl of 1 to 6 carbons or R¹ and R⁸ taken together form a group (CH₂)_v wherein v is 1 to 7;
• R² is
  
  where
• each R⁸ is independently H, OH, C₁ to C₄-O-alkyl or alkyl of 1 to 4 carbons; or an R¹ and an R⁸ taken together form a group (CH₂)_v wherein v is 1 to 7,
• R⁹ is COOR¹; CH₂OH; CHO; tetrazole; NHSO₂R¹⁰ wherein R¹⁰ is OH, alkyl or alkoxy of 1 to 6 carbons, perhaloalkyl of 1 to 6 carbons, phenyl or phenyl substituted by alkyl or alkoxy groups of 1 to 3 carbons, halogen, hydroxy, COOH, CN, formyl or acyl of 1 to 6 carbons; CONHSO₂R¹⁰; hydroxymethylketone; CN; or CON(R⁸)₂;
• X is O; S; SO; S0₂; NR¹¹ wherein R¹¹ is H, alkyl of 1 to 6 carbons, acyl of 1 to 6 carbons, CN; CR¹R⁸;
  
  or the unit wherein the dotted line represents an optical triple bond and in which the R¹ and R⁸ substituents are absent when a triple bond is present;
• r and q are each independently 0 to 5 and p is 0 or 1 provided that the total of p, q and r is 2 to 6;
• R³ is H, alkyl of 1 to 6 carbons; phenyl or phenyl substituted by R⁴; or C₁ to C₄ alkylphenyl or C₁ to C₄ alkylphenyl in which the phenyl is substituted by R⁴;
• R⁴, R⁵, R⁶ and R⁷ are each independently selected from:
  • (1) hydrogen;
  • (2) alkyl having 1 to 6 carbon atoms;
  • (3) alkenyl having 2 to 6 carbon atoms;
  • (4) -(CH₂)_nM
    
    wherein n is 0 to 3 and M is
    • a) OR¹²;
    • b) halogen;
    • c) CF₃;
    • d) SR¹²;
    • e) phenyl or substituted phenyl wherein substituted phenyl is as defined below in the definition of R¹²;
    • ^f) COOR¹³;
    • g)
    • h) tetrazole;
    • i) wherein R¹⁵ is C₁ to C₆ alkyl, benzyl or phenyl;
    • j) -NR¹³R¹³;
    • k) -NHSO₂R¹⁶ wherein R¹⁶ is C₁ to C₆ alkyl, phenyl, or CF₃;
    • I)
    • m) -SOR¹²;
    • n) -CON¹³R¹³;
    • o) -SO₂NR¹³R¹³;
    • p) -SO₂R¹²;
    • q) N0₂;
    • r)
    • s)
    • t)
    • u) CN;
• each R¹² independently is H; C₁ to C₆ alkyl; benzyl; phenyl or substituted phenyl wherein the substituents are C₁ to C₃ alkyl, halogen, CN, CF₃, COOR¹³, CH₂COOR¹³, C₁ to C₃ alkoxy, or C₁ to C₄ perfluoroalkyl;
• each R¹³ is independently H, phenyl or C₁ to C₆ alkyl; and,
• each R¹⁴ independently is H, (CH₂)_nCOOR¹³ wherein n is 0 to 4, C₁ to C₆ alkyl, CF₃, phenyl, or substituted phenyl wherein substituted phenyl is as defined above in the definition of R¹²;

A silver halide photographic light-sensitive material comprising a support and at least one silver halide emulsion layer wherein the silver halide photographic light-sensitive material contains at least one compound represented by the following general formula (I): wherein COUP represents a coupler residue capable of undergoing a coupling reaction with an oxidation product of an aromatic primary amine developing agent; TIME represents a timing group which is released from COUP the coupling reaction and subsequently releases represents a group capable of being released from COUP by the coupling reaction when n is 0, or a group capable of being released from TIME after TIME which has been released from COUP when n is 1, AD being adsorptive to silver halide particles; R represents an alkyl group, an aryl group or a heterocyclic group; R' and R", which may be the same or different, each represents a hydrogen atom or a substitutent; and -NHNHCOR may be directly connected to AD when AD is combined with the benzene ring to form a condensed ring system.

The'silver halide photographic light-sensitive material containing the compound represented by general formula (I) is improved in stability during storage and has a high sensitivity.

Novel fluorophenoxyphenoxypropionates and derivatives thereof and compounds related thereto possess herbicidal activity selectively in the presence of broadleaf crops. Preemergent and postemergent applications are contemplated.

The compounds are of the formula wherein

• X represents -F, -Cl, -Br, -I, -CF₃, -OCF₃, -CF₂CI, -CF₂H or-CF₂CCl₂H; and
• Z represents an organic moiety, the moiety containing N, O or S atoms, a metallic cation, an ammonium cation or an organic amine cation and is, or can be hydrolyzed and/or oxidized in plants or soil to, a carboxyl moiety that is in undissociated and/or dissociated form.
• Preferably Z ist or an agriculturally acceptable salt, amide or ester thereof.
• Also provided are novel intermediates of the formula wherein
• Y is OH, NH₂ or N₂⊕ BF₄⊖, as well as herbicidal compositions and a method of controlling weeds by applying to them one or more of the active compounds of the invention.

Chemical compounds are provided that are novel substituted benzothiopyrano[4,3,2-cd]indazoles, as well as methods for their production, pharmaceutical compositions comprising the compounds, and methods of treatment using the compounds in dosage form. Compounds of the invention have pharmacological properties and are useful antibacterial agents, antifungal agents, and antitumor agents.

1-[2-(2,4-Dichlorphenyl)pentyl]-1H-7,2,4-triazol kann nach einem neuen einfachen und wirtschaftlichen Verfahren in isomerenfreier Form hergestellt werden, indem man 2-(2,4-Dichlorphenyl)-valero-nitril in Gegenwart von Wasserstoff, einer Säure und eines Hydrierungskatalysators mit einer Verbindung H₂N-NH-R zu einer Verbindung der Formel umsetzt, die Verbindung (III) katalytisch zu einer Verbindung hydriert, Verbindungen (IV) mit R ungleich H hydrolysiert und die Verbindungen (IV) mit R=H oder Salze davon mit Formamid und/oder [3-(Dimethylamino)-2-azaprop-2-en-1-yliden]-dimethylammoniumchlorid in das 1-[2-(2,4-Dichlorphenyl)pentyl]-1H-1,2,4-triazol überführt, oder Verbindungen (IV) mit R = -COR' mit wässriger Ameisensäure in die entsprechenden N,N'-Bisformylderivate überführt und diese mit Formamid, gegebenenfalls in Gegenwart von NH₃, zum 1-[2-(2,4-Dichlorphenyl)pentyl)-1H-1,2,4-triazol umsetzt. Dabei ist R Wasserstoff, -CHO, -COR', -COOR' oder -CONH₂ und R' bedeutet C_1-4-Alkyl, Benzyl oder Phenyl. Das 1-[2-(2,4-Dichlorphenyl)-pentyl)-1H-1,2,4-triazol besitzt funizide Wirkung und kann zur Bekämpfung phytopathogener Pilze verwendet werden.

A compound of the formula or its pharmaceutically acceptable salt: where, in one example. R' is n-octanoyl, n is the integer O, R₂ is benzyl, R₃ is 1-carboxyethylammo, R₄ is hydrogen and R⁵ is hydrogen and processes for their preparation and also a pharmaceutically composition comprising, as an effective ingredient, the above compound in association with pharmaceutically acceptable carriers.

N-Phenylpyrazole derivatives of the formula:- (wherein each of R⁵ and R⁶ represents a C₁-C₄ alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R', R' and R⁹ represents a hydrogen atom, a C₁-C₄ alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R⁵, R⁷, R' and R⁹ each represents a hydrogen atom and R⁶ represents a trifluoromethoxy or trifluoromethyl radical, and R¹⁰ represents a cyano radical or substituted carbamoyl radical -CONHR", wherein R" represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1- (4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the prepararation of the new compounds.

N-Phenylpyrazole derivatives of the formula:- (wherein each of R⁵ and R⁶ represents a C₁-C₄ alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical, or a fluorine, chlorine or bromine atom, each of R', R' and R⁹ represents a hydrogen atom, a C₁-C₄ alkyl or alkoxy radical, a trifluoromethyl, trifluoromethoxy, nitro, cyano or primary amino radical or a fluorine, chlorine or bromine atom, or R⁵, R⁷, R' and R⁹ each represents a hydrogen atom and R⁶ represents a trifluoromethoxy or trifluoromethyl radical, and R¹⁰ represents a cyano radical or substituted carbamoyl radical -CONHR", wherein R" represents a methyl or ethyl radical) have been found to possess useful herbicidal properties. All such N-phenylpyrazole derivatives with the exception of 5-amino-4-cyano-1-(2,4-dichlorophenyl)pyrazole and 5-amino-4-cyano-1- (4-chloro-2-methylphenyl)pyrazole are new compounds. Herbicidal compositions containing such N-phenylpyrazole derivatives are described and also processes for the prepararation of the new compounds.

Formylderivate von Hydrazinomethylpenicillinen der Formel worin

• R für einen Thienyl- oder Phenylrest steht,
• R' Wasserstoff, einen Formylrest oder einen Alkylrest mit 1 bis 3 Kohlenstoffatomen bedeutet,
• R" Wasserstoff oder einen Formylrest darstellt und
• das Sternchen (*) ein Asymmetriezentrum des Moleküles darstellt, mit der weiteren Maßgabe, daß
  
  mindestens eines von R' und R" einen Formylrest darstellt,

Diese Verbindungen können in Arzneimitteln auf dem Gebiet der Therapie, insbesondere als antibakterielle beziehungsweise baktericide Mittel verwendet werden.

2-hydroxyoxanilic acid derivatives shown by the following formula and salts thereof possess an immunoregulatory action and can be useful as antiallergic agents, antiasthmatics, antirheumatics, carcinostatic agents, therapeutic agents for autoimmune disease, and suppressants of rejection in tissue transplants and skin grafts. They can be made from the corresponding aminophenols and oxalylic acids.

A compound of the formula or its pharmaceutically acceptable salt:

• wherein R¹ is hydrogen or acyl;
• R₂ is carboxy or protected carboxy or a group of the formula:
  • -COHN-R² wherein R²a is carboxy(lower)alkyl or protected carboxy(lower)alkyl;
• R³ is carboxy, protected carboxy, lower alkyl, hydroxyphenyl, carbamoyl ora graup oftheformula: R³a-CH-R³b wherein R³a is hydrogen, amino, protected amino or a cylamino, R³b is carboxy or protected carboxy;
• R^Pis carboxy, protected carboxy, carbamoyl, carboxy(lower)alkyl or protected carboxy(lower)alkyl; ℓ isaninteger0or2, m is an integer 0 to 3 and n is an integer 0 to 1, with certain provisions, and pharmaceutically acceptable salts thereof and process for their preparation, and also a pharmaceutical composition comprising, as an effective ingredient, the above compound in association with a pharmaceutically acceptable, substantially nontoxic carrier or excipient.

Heterocyclic compounds of formula (I) and their acid addition salts exhibit anti-inflammatory activity and when administered topically do not provide the side-effects associated with their systemic administration. The novel compounds of formula (I) may be prepared by methods known in the art and may be topically administered as the compound alone or in a suitable pharmaceutical formulation.

2-Substituted-3-heterocyclyl-indoles of the formula wherein X is a hydrogen or halogen atom,

• n is 1, or 3 (when X is halogen atom),
• Q is an oxygen atom or the group (H, OH),
• Z is a hydrogen atom or, provided that Q is an oxygen atom, Z can also be the group OR, wherein R is a hydrogen atom or a lower alkyl or loweralkoxy-loweralkyl group,
• m is 1 or 2 when Z is a hydrogen atom and m is O when
• Z is the group OR,
• and Het is a heterocyclic radical selected from pyridyl, lower-alkyl-substituted pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, thienyl, furanyl, pyrrolyl, oxazolyl and isoxazolyl, have immuno-suppressant activity and can be used for example in the treatment of rheumatoid arthritis.

Their preparation and pharmaceutical compositions containing them are also described.

A photographic element is provided which contains a substituted 1-phenyl-3-pyrazolidinone electron transfer agent. Such electron transfer agent has the following formula: wherein:

• R is hydrogen or a hydrolyzable moiety;
• R₁ is hydrogen or a hydroxy group;
• R₂, R₃ and R₄ each represent hydrogen, hydroxy, an alkyl group of 1 to 3 carbon atoms, an alkoxy group of 1 to 3 carbon atoms, a phenyl group, -NHSO₂R₅, -O(CH₂)_nOR₆, -(CH₂)_nOR₆, -O(CH₂)_nC₆H₅, -(CH₂)_nR₇, or -O(CH₂)_nR₇;
• R₅ is hydrogen or an alkyl group of 1 to 3 carbon atoms;
• R₆ is hydrogen or a methyl group;
• R₇ is NHSO₂R₅ or SO₂NHR₅; and
• n is a positive integer of 1 to 2;

Novel compounds are provided of the general formula wherein R^I represents a hydrogen atom, an optionally substituted cycloalkyl group having 3 to 5 ring carbon atoms and a total of 3 to 6 carbon atoms, or an alkyl group having 1 to 4 carbon atoms or an alkenyl group having 2 or 3 carbon atoms which groups may be unsubstituted or substituted by one or more fluorine, chlorine and/or bromine atoms; R² represents a fluorine, chlorine or bromine atom, a trifluoromethyl, nitro or cyano group, or an alkyl, alkoxy or alkylthio group having from 1 to 6 carbon atoms; and A represents various optionally-substituted 5-membered heterocycles containing up to 3 nitrogen atoms and also in some cases an oxygen atom. These compounds have herbicidal activity.