US 5,449,809 AGranted

Acetylene derivatives and crop protection agents containing them

AssigneeBASF SE

InventorsHorst Wingert, Beate Hellendahl, Reinhard Kirstgen, Hubert Sauter, Eberhard Ammermann, Gisela Lorenz

Life of this patent

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Abstract

Acetylene derivatives of the general formula I ##STR1## where U, V and W are hydrogen, halogen, nitro, cyano, alkyl or alkoxy, A is alkylidene, alkoxymethylidene, alkylthiomethylidene or alkoximino, B is OH, alkoxy or alkylamino and R is hydrogen, halogen, cyano, CF.sub.3, alkyl, cycloalkyl, haloalkyl, aryl, alkenyl, alkynyl, heterocyclyl, hetaryl, arylalkyl, arylalkenyl, arylethynyl, hetaryl-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, aryloxyalkyl, hetaryloxyalkyl, arylamino-alkyl, arylthiomethyl, hetarylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, SiR.sup.12 R.sup.13 R.sup.14, SnR.sup.15 R.sup.16 R.sup.17, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 and R.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are hydrogen, alkyl, aryl, hetaryl, arylalkyl or hetarylalkyl and R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or aryl-C.sub.1 -C.sub.4 -alkoxy, and fungicides containing these compounds.

Claims10

Dependent claims

An acetylene derivative of the formula I ##STR32## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,

A is C.sub.1 -C.sub.4 -alkoximino,
B is OH or C.sub.1 -C.sub.4 -alkoxy and
R is hydrogen, halogen, cyano, CF.sub.3, straight-chain or branched C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, unsubstituted or substituted aryl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl-C.sub.2 -C.sub.4 -alkenyl, unsubstituted or substituted arylethynyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylamino-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 and
R.sup.1 --R.sup.17, R.sup.19 and R.sup.20 are identical or different and are each hydrogen, C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl or unsubstituted or substituted arylalkyl,
R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkoxy,
the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl and Me is methyl and Et is ethyl, with the exception of the following individual compounds of the formula I where
A=CHOCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHSCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHCH.sub.3, B=OCH.sub.3, and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=OCH.sub.3 and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl,
A=CHOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl and
A=CHSCH.sub.3, B=NHCH.sub.3, R=phenyl.

10 more elements

A fungicide containing an inert carrier and a fungicidally effective amount of an acetylene derivative of the formula I ##STR35## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,

A is C.sub.1 -C.sub.4 -alkoximino,
B is OH or C.sub.1 -C.sub.4 -alkoxy and
R is hydrogen, halogen, cyano, CF.sub.3, straight-chain or branched C.sub.1 -C.sub.10 -alkyl, C.sub.3 --C.sub.6 -cycloalkyl, unsubstituted or substituted aryl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl-C.sub.2 -C.sub.4 -alkenyl, unsubstituted or substituted arylethynyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylamino-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylthiomethyl, C(O)R.sup.1, C(O)NR.sup.2 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 and
R.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are identical or different and are each hydrogen, C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl or unsubstituted or substituted arylalkyl,
R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkoxy,
the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl and Me is methyl and Et is ethyl, with the exception of the following individual compounds of the formula I where
A=CHOCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHSCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHCH.sub.3, B=OCH.sub.3, and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=OCH.sub.3 and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl,
A=CHOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl and
A=CHSCH.sub.3, B=NHCH.sub.3, R=phenyl.

10 more elements

A method of combatting fungi, wherein the fungi, or the materials, plants or seeds to be protected against fungus attack, or the soil are treated with a fungicidally effective amount of a compound of the formula ##STR36## where U, V and W are identical or different and are each hydrogen, halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy,

A is C.sub.1 -C.sub.4 -alkoximino,
B is OH or C.sub.1 -C.sub.4 -alkoxy and
R is hydrogen, halogen, cyano, CF.sub.3, straight-chain or branched C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, unsubstituted or substituted aryl, halo-C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl-C.sub.2 -C.sub.4 -alkenyl, unsubstituted or substituted arylethynyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted aryloxy-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylamino-C.sub.1 -C.sub.4 -alkyl, unsubstituted or substituted arylthiomethyl, C(O)R.sup.1, C(O)NR.sup.1 R.sup.3, C(S)NR.sup.4 R.sup.5, C(O)SR.sup.6, C(S)OR.sup.7, C(S)SR.sup.8, CH(OH)R.sup.9, CH(OR.sup.10)R.sup.11, C(OR)R.sup.18 or C(.dbd.N--OR.sup.19)R.sup.20 and
R.sup.1 -R.sup.17, R.sup.19 and R.sup.20 are identical or different and are each hydrogen, C.sup.1 -C.sub.4 -alkyl, unsubstituted or substituted aryl or unsubstituted or substituted arylalkyl,
R.sup.18 is OH, C.sub.1 -C.sub.4 -alkoxy or unsubstituted or substituted aryl-C.sub.1 -C.sub.4 -alkoxy,
the term "unsubstituted or substituted" denoting, in addition to hydrogen, halogen, cyano, nitro, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkoximino-C.sub.1 -C.sub.4 -alkyl, aryl, aryloxy, benzyl, benzyloxy, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.4 -dialkylamino, CO.sub.2 Me, CO.sub.2 Et, formyl or acyl and Me is methyl and Et is ethyl, with the exception of the following individual compounds of the formula I where
A=CHOCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHSCH.sub.3, B=OCH.sub.3 and R=phenyl
A=CHCH.sub.3, B=OCH.sub.3, and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=OCH.sub.3 and R=phenyl, 2-fluorophenyl, 2-chlorophenyl, 2-bromophenyl, 2-methoxyphenyl, 2-nitrophenyl, 2-methylphenyl, 4-bromophenyl, 4-trifluoromethylphenyl or 4-methylphenyl,
A=NOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl,
A=CHOCH.sub.3, B=NHCH.sub.3, R=CH.sub.3, phenyl and
A=CHSCH.sub.3, B=NHCH.sub.3, R=phenyl.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/099,693Filed 30 Jul 1993
Priority: DE 42 26 557.611 Aug 1992
Granted: 12 Sep 1995
Term ends: Not estimatedThe source records don’t support an estimate.

Classification23 codes

C07D 271/107
1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles: with two aryl or substituted aryl radicals attached in positions 2 and 5
A01N 37/36
Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to…:…
A01N 37/50
Containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton…
A01N 43/10
Five-membered rings: with sulfur as the ring hetero atom