Amino acid amide derivatives and their use as pesticides

Details Amino acid amide derivatives and their use as pesticides Amino acid amide derivatives and their use as pesticides

1997-07-16

1999-08-10

Davis, Zinna Northington

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514469, 514616, 546335, 549467, 564152, 564155, C07D21340, A01N 4340

Patent

active

059359790

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel substituted amino acid amides, to a process for their preparation and to their use as pesticides.
It is known that certain substituted amino acid amides such as, for example, the compound compound de} have fungicidal properties (cf. for example EP 398 072).
However, the activity of these prior art compounds is, in particular at low application rates and concentrations, not entirely satisfactory in all areas of application.
This invention accordingly provides the novel amino acid amides of the general formula (I) ##STR1## in which A represents a single bond or optionally substituted alkylene, oxygen or sulphur, alkinyl, cycloalkyl, cycloalkenyl, arylalkyl, aryl, heterocyclylalkyl or heterocyclyl, respectively optionally substituted alkyl, or cycloalkyl, or form an optionally substituted carbocyclic ring and cycloalkenyl, aryl or heterocyclyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, also in connection with hetero atoms, such as in alkoxy, alkylthio or alkylamino, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
Aryl represents aromatic, mono or polycyclic hydrocarbon rings, such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated and aromatic compounds in the form of a ring in which at least one ring member is a hetero atom, i.e. an atom that is different from carbon. If the ring contains more than one hetero atoms, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. The compounds in the form of a ring together with further carbocyclic or heterocyclic, fused or bridged rings optionally form a polycyclic ring system. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Cycloalkyl represents saturated carbocyclic compounds in the form of a ring which together with further carbocyclic, fused or bridged rings optionally form a polycyclic ring system.
Cycloalkenyl represents carbocyclic compounds in the form of a ring which contain at least one double bond and which together with further carbocyclic, fused or bridged rings optionally form a polycyclic ring system.
Furthermore, it was found that the novel amino acid amides of the general formula (I) are obtained when N-substituted amino acids of the general formula (II) ##STR2## in which Q.sup.1, Q.sup.2, Q.sup.3, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each as defined above are reacted with amines of the general formula (III), ##STR3## in which A, R.sup.5 and R.sup.6 are each as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent.
Finally, it was found that the novel amino acid amides of the general formula (I) have a very strong fungicidal activity.
The compounds according to the invention may be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and optical isomers. What is claimed includes both the E and the Z isomers, and also the threo and erythro and the optical isomers and any mixtures of these isomers.
The invention preferably provides compounds of the formula (I) in which optionally mono- or polysubstituted by identical or different substituents, the possible substituents preferably being selected from the following list: thiocarbamoyl; or alkylsulphonyl having in each case 1 to 6 carbon atoms; each case 2 to 6 carbon atoms; halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 13 identical or different halogen atoms; alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkylsulphonyloxy, hydroximinoalky

REFERENCES:
Bull. Chem. Soc. Jpn. (1993), 66(7), 2048-53, XP002001309, Shin, Chugn Gi, et al., "Dehydrooligopeptides. XV. Useful syntheses of dehydrodipeptides by the enzymic coupling of. alpha-dehydroglutamate . . . proteases".
Bull. Chem. Soc. Jpn. (1980), 53(10), 2905-9, XP002001312, Yonezawa, Yasuchika, et al. "Dehydrooligopeptides. I. The facile coupling of .alpha.-dehydroamino acids with . . . dehydrodipeptides".
Chemical Abstracts, vol. 118, No. 21, May 24, 1993, Abstract No. 212719, Ueda, Y. et al. "Synthesis of alpha.-(S)-acylamino-N-(hydroxydioxocyc . . . antibiotics".
Chemical Abstracts, vol. 110, No. 21, May 22, 1989, Abstract No. 193407, Shin Shigeki, et al. "A process for preparation . . . them".
Bull. Chem. Soc. JPN. (1988), 61(7), 2687-9, XP002001310, Yonezawa, Yasuchika, et al. "Dehydrooligopeptides. IX. Syntheses and conversions . . . dipeptides".
Bull Chem. Soc. JPN. (1986), 59(11), 3573-9, XP002001311, Shin, Chung Gi, et al. "Dehydrooligopeptides. VII. Convenient synthesis . . . anhydride".
Bull. Chem. Soc. JPN. (1995), 68(12), 3549-55, XP002001313, Shin, Chung-Gi, et al. "Dehydrooligopeptides. XVIII. Enzymic . . . papain".
Ueda et al, Chemical Abstracts vol. 118, No. 21, No. 212, 719, May 24, 1993.
Shin et al. Chemical Abstracts, vol. 110, No. 21, No. 193, 407, May 22, 1989.
Yonezawa et al, Bull. Chem. Soc. Jpn, vol. 53, No. 10, pp. 2905-2909, 1980.

Affiliated with

Also associated with

Rating

Amino acid amide derivatives and their use as pesticides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Amino acid amide derivatives and their use as pesticides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Amino acid amide derivatives and their use as pesticides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1120546