KR950011427A - Cyanophenyliminoheterocycles - Google Patents

Abstract

The present invention relates to novel 4-cyanophenyliminoheterocycles of the general formula (I), to various preparations thereof, to their use as herbicides and to the novel intermediates for synthesizing them.

Wherein R ¹ is hydrogen or halogen and R ² is halogen, cyano, hydroxyl, amino, or a group -XR ³ -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) -SO ₂ R ⁵ wherein X represents oxygen, sulfur or a single bond and R ³ is each independently selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl , Heterocyclyl or heterocyclylalkyl, R ⁴ represents hydrogen or alkyl, and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyne, cycloalkylalkyl, aryl, or arylalkyl, A represents an optionally substituted alkanediyl or alkenediyl, E represents nitrogen or carbon, G represents nitrogen, or may be bonded to hydrogen or alkyl via an exo single bond or through an exo double bond Oxygen or carbon bonded to sulfur Wherein when A represents nitrogen, A does not represent optionally substituted trimethylene.

Description

Cyanophenyliminoheterocycles

Since this is a trivial issue, I did not include the contents of the text.

Claims (14)

The 4-cyanophenyliminoheterocycle of general formula (I). Wherein R ¹ is hydrogen or halogen and R ² is halogen, cyano, hydroxyl, amino, or a group -XR ³ -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) -SO ₂ R ⁵ wherein X represents oxygen, sulfur or a single bond and R ³ is each independently selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl , Heterocyclyl or heterocyclylalkyl, R ⁴ represents hydrogen or alkyl, and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, A represents an optionally substituted alkanediyl or alkenediyl, E represents nitrogen or carbon, G represents nitrogen, or may be bonded to hydrogen or alkyl via an exo single bond or through an exo double bond Oxygen or carbon bonded to sulfur Wherein when A represents nitrogen, A does not represent optionally substituted trimethylene. The method of claim 1, wherein, R ¹ represents hydrogen, fluorine, chlorine or bromine, R ² is fluorine, chlorine, bromine, cyano, hydroxyl, amino or geureup ^{-XR 3, -N (R 4)} -CO- R ⁵ or -N (R ⁴ ) -SO ₂ R ³ wherein X represents oxygen, sulfur or a single bond and R ³ represents fluorine, chlorine, bromine, cyano, carboxyl, C _{1- 4} - alkoxy, C _l-4-alkoxy-l -C ₄ - alkoxy, C _l-4 - alkali alkylthio, C _1-4 - alkylcarbonyl, C _l-4 alkoxy-carbonyl or C _5-8 - cycloalkyloxy-carbonyl, or optionally represents a substituted carbon atom number of 1 to 8 alkyl by, R ³ is also fluorine, chlorine or in each case a by bromine, optionally substituted alkenyl the carbon atom number of 2 to 8, the Al or in each case Alkynyl or R ³ is also optionally substituted in each case by fluorine, chlorine, bromine, cyano, carboxyl, C _1-4 -alkyl or C _1-4 -alkoxy-carbonyl, Alkyl Benzyl, phenylethyl, phenylpropyl or phenylbutyl optionally substituted in each case with the proviso that when the alkyl moiety has 3 to 8 carbon atoms and optionally has 1 to 4 carbon atoms in the alkyl moiety, Or in each case at least one of the ring members is an oxygen, sulfur or nitrogen atom and, optionally, from 1 to 3 are further nitrogen atoms, and in each case optionally substituted heterocyclyl, heterocyclylmethyl Heterocyclyl group, wherein the heterocyclyl group is optionally saturated or unsaturated and the cyclic group is optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, nitro, carboxyl, carbamoyl, C ₄ -alkyl, Ci _-4 -halogenoalkyl, Ci _-4 -alkoxy Ci ₄ -halogenoalkoxy Ci ₄ -alkylthio, Ci ₄ -halogenoalkylthio , C _{l-4-alkoxy-carbonyl-alkyl} sulfinyl, C _{l-4-halogeno-alkyl} sulfinyl, C _l-4 -alkyl sulfonyl, C _{l-4-halogeno-alkylsulfonyl} and C _l-4 R ⁴ is hydrogen or alkyl having 1 to 8 carbon atoms and R ⁵ is selected from the group consisting of fluorine, chlorine, bromine, cyano, carboxyl, C _1-4 -alkoxy, C _{1-4 -alkoxy-l} -C ₄ - alkoxy, C _l-4-alkaline alkylthio, C _{l-4-alkyl-carbonyl} or C _l-4 - alkoxy - optionally being substituted by a carbonyl, the number of carbon atoms from 1 to 8, represent alkyl, or, R ³ can also in each case a by fluorine, chlorine or bromine, in each case optionally substituted indicate the number of carbon atoms from 2 to 8, alkenyl or alkynyl in or, R ³ is also fluorine, chlorine in each case C _1-4 -alkyl or C _1-4 -alkoxy-carbonyl, which in each case has 3 to 8 carbon atoms in the cycloalkyl moiety and is optionally substituted by alkyl Cycloalkyl or cycloalkylalkyl optionally having 1 to 4 carbon atoms in the moiety, or in each case by fluorine, chlorine, bromine, cyano, nitro, carboxyl, carbamoyl and in each case fluorine and / or chlorine the arbitrarily substituted by C _l-4 - alkyl, C _l-4 - alkoxy, C _l-4 - alkali alkylthio, C _l-4 - alkylsulfinyl or C _l-4 - by alkyl sulfonyl, and dimethylamino C _1-4 -alkoxy-carbonyl which is unsubstituted or substituted by fluorine, chlorine, bromine, methoxy or by ethoxy, and in each case fluorine, chlorine, bromine, iodine, Cyano, methyl, methoxy, trifluoromethyl. Optionally substituted by phenyl, phenylmethyl, phenoxy, phenylthio, phenylsulfinyl or phenylsulfonyl optionally substituted by trifluoromethoxy and / or trifluoromethoxy and optionally substituted by 5 or 17 carbon atom substituents Optionally substituted by C _1-4 -alkyl optionally in each case optionally fluorine, chlorine, bromine, or by fluorine and / or chlorine, and A represents an arylalkyl or aryl having 8-4 carbon atoms, substituted and represents a carbon atom number of 2 to 6 Al or Al kaldi one canned days in each case, E represents a carbon or nitrogen, G represents a nitrogen or frame, hwanoe (exo) or hydrogen through a single bond C _l- Represents a carbon bonded to ₄ -alkyl or bonded to oxygen or sulfur through an extramolecular double bond, wherein E represents nitrogen, A represents an optionally substituted trimethylene, Cyanophenyliminoheterocycle of formula (I). The method of claim 1, wherein, R ¹ represents hydrogen, fluorine, or chlorine, R ² is fluorine, chlorine, bromine, cyano, hydroxyl, amino, or a group ^{-XR 3, -N (R 4)} -CO-R 5 Or -N (R ⁴ ) -SO ₂ R ⁵ , wherein X represents oxygen, sulfur or a single bond and R ³ in each case is fluorine, chlorine, bromine, cyano, carboxyl, methoxy Ethyl, n- or i-propyl optionally substituted by methoxy, ethoxy, methoxyethoxy, ethoxyethoxy, methylthio, ethylthio, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, Or an allyl, crotone, 1-methyl-allyl, propargyl or 1-methyl-pro optionally substituted by fluorine or chlorine, or represents R ³ can also in each case fluorine, chlorine, methyl, ethyl, n- or i- propyl, methoxycarbonyl or ethoxycarbonyl by a carbonyl optionally substituted cyclopropyl, Inc. Claw-butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, or represents a cyclohexylmethyl, R ⁴ is hydrogen, methyl, ethyl, n- or i- propyl, or n-, i-, R ⁵ represents in each case fluorine, chlorine, bromine, cyano, carboxyl, methoxy, ethoxy, methoxyethoxy, ethoxyethoxy, methylthio, ethylthio, acetyl, Methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl optionally substituted by methoxycarbonyl or ethoxycarbonyl, or R < ^{3 &} Chlorine, cetonyl, 1-methylallyl, propargyl or 1-methyl-propargyl, optionally substituted by fluorine or chlorine, or R ³ may also represent fluorine, chlorine, Or cyclopropyl optionally substituted by i-propyl, cyclobutyl, cyclopentyl, Cycle as cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclo pintil or represent methyl or cyclohexylmethyl. R < ⁵ > may also be in each case optionally substituted with one or more substituents selected from the group consisting of fluorine, chlorine, bromine, cyano, methyl, ethyl, n- or i-propyl, n-, s- or t- , Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulfinyl, trifluoromethylsulfinyl, Phenyl, naphthyl, benzyl or phenylethyl optionally substituted by phenyl, phenoxy or phenylsulfonyl, A represents in each case fluorine, chlorine Propane-1,3-diyl (trimethylene), butane-1,4-diyl (texramethylene), 1-propene-1, 1-butene-1, 4-diyl or 2-butene-1, 4-diyl, E represents nitrogen or carbon, G represents nitrogen, (exo) hydrogen, methyl, ethyl, n- or i-propyl through a single bond; represents a carbon bonded to the oxygen via an exo-double bond, and when E represents nitrogen, A represents an optionally substituted trimethylenene represented by the formula ( I) < / RTI > of 4-cyanophenyliminoheterocycles. The 4-cyanophenyliminoheterocycle of formula (1A). Wherein R ¹ is hydrogen or halogen and R ² is halogen, cyano, hydroxyl, amino or a group -XR ³ , -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) It represents one of the S0 ₂ R ^5, where, X is oxygen, sulfur or a single bond, R ³ are each an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, R ⁴ represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each of A Each independently represent optionally substituted alkanediyl or alkenediyl. The 4-cyanophenyliminoheterocycle of formula (IB). Wherein R ¹ is hydrogen or halogen and R ² is halogen, cyano, hydroxyl, amino or a group -XR ³ , -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) It represents one of the S0 ₂ R ^5, where, X is oxygen, sulfur or a single bond, R ³ are each an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, R ⁴ represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each of A Each independently represent optionally substituted alkanediyl or alkenediyl, with the exception of the de-substituted trimethylene. (a) reacting a substituted thiocarbonylamino compound of the general formula (II) with an oxidizing agent or a dehydrogenating agent, optionally in the presence of a reaction aid and optionally in the presence of a diluent, or (b) With a phosgene, optionally in the presence of a diluent, or (C) reacting a cyanoaryliminoheterocycle of general formula (Ia), optionally in the presence of an acid acceptor and optionally Cyanophenyl of the formula (I) according to claim 1, characterized in that it is reacted with a nucleophilic compound of the formula (IV) or (V) or an alkali metal salt of these compounds in the presence of a diluent. Lt; / RTI > Wherein A, R ¹ , R ² , E, G, X, R ³ , R ⁴ and R ⁵ are as defined in claim ¹ and X ¹ is halogen. A herbicide which is characterized in that it contains at least one 4-cyanophenyl iminoheterocycle of the general formula (I) according to any one of claims 1 to 3 and 6. Characterized in that the 4-cyanophenyl iminoheterocycle of formula (I) according to any one of claims 1 to 3 and 6 acts on plants and / or their habitats, How to. Use of 4-cyanophenyliminoheterocycles of general formula (I) according to claims 1 to 3 and 6 for the control of unwanted plants. Characterized in that the 4-cyanophenyliminoheterocycle of the general formula (I) according to claims 1 to 3 and 6 is mixed with a weight and / or a surfactant. A substituted thiocarbonylamino compound of formula (II). Wherein R ¹ is hydrogen or halogen and R ¹ is halogen, cyano, hydroxyl, amino, or a group -XR ³ , -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) SO ₂ R ⁵ wherein X represents oxygen, sulfur or a single bond and R ³ is each independently selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, R ⁴ represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each of A Each independently represent optionally substituted alkanediyl or alkenediyl. Substituted tert-carbonylamino compounds of formula (III). Wherein R ¹ is hydrogen or halogen and R ¹ is halogen, cyano, hydroxyl, amino, or a group -XR ³ , -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) SO ₂ R ⁵ wherein X represents oxygen, sulfur or a single bond and R ³ is each independently selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, R ⁴ represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, each of A Each independently represent optionally substituted alkanediyl or alkenediyl. Cyanauryl isothiocyanate of general formula (VIII). Wherein R ¹ is hydrogen or halogen and R ¹ is halogen, cyano, hydroxyl, amino, or a group -XR ³ , -N (R ⁴ ) -CO-R ⁵ or -N (R ⁴ ) SO ₂ R ⁵ wherein X represents oxygen, sulfur or a single bond and R ³ is each independently selected from optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, R ⁴ represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, or arylalkyl, each of which is optionally substituted; , 3-trifluoromethyl-4-cyano-phenyl isothiocyanate and 3-chloro-4-cyanophenyl isothiocyanate of the compound of formula (VIII) are excluded. Substituted 4-cyanoanilines of formula (Xa). Wherein R ¹ represents hydrogen or halogen, R ² represents hydrogen or alkyl and R ⁵ represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl, Y represents CO or SO ₂ . ※ Note: It is disclosed by the contents of the first application.