Aminobutyric acid fungicides

Details Aminobutyric acid fungicides Aminobutyric acid fungicides

1999-06-25

2002-02-19

Killos, Paul J. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

C560S038000, C560S043000, C562S443000, C562S450000, C564S162000, C564S163000, C514S538000, C514S562000, C514S618000, C514S619000

Reexamination Certificate

active

06348614

ABSTRACT:

The present invention concerns a novel method to protect plants from pathogenic attack.
BACKGROUND OF THE INVENTION
The use of threo-DL-&bgr;-methylaspartic acid and of DL-&bgr;-aminobutyric acid for the control of root rot of peas caused by
Aphanomyces euteiches
Drechs, has been described (Papavizas, Plant Disease Reporter, 48, 537-541 (1964), Papavizas, Plant Disease Reporter, 51, 125-129 (1967).
The use of D-alaninie, D-and DL leucine and DL-&agr;-aminobutyric acid at 0.03 M was described to reduce scab in apple caused by
Venturia inaequalis
(Kuc et al., 49: 313-315, 1959).
Van Andel, showed (Tijdschur. Plantenziekten. 64: 307-327, 1958) that DL-serine, D-serine (and to a lesser extent L-serine), phenylserine, DL-threonine but not DL-&agr; aminobutyric acid nor DL-&bgr; aminobutyric acid behaved as chemothrerpeutants against the fungus
cladosporium cucumerinum
on cucumber (Ibid. page 318). Oort and Van Andel (1960, Mededel. Landsborowhager school Dpzoekingssta. Staat Gent 25: 981-992) showed that DL-&bgr;-aminobutyric acid applied to leaves of tomato protected those leaves against
Phytophthora infestans
(page 987).
Various derivatives of DL-&bgr;-aminobutyric acid and &bgr;-aminocrotonic acid have been described in the patent literature as fungicides against
Phytophthora infestans
in tomato and
Plasmopara viticola
in grapes (German Patent No. 1,120,802).
Co-pending Israel Patent Application No. 111,824 describes the preparation and use of similar compounds which induce local and systemic resistance of crops against fungal diseases.
OBJECTIVES OF THE INVENTION
It is the objective of the present invention to provide compounds having improved activity against fungi as compared with the compounds of the co-pending Israel patent application 111,824.
SUMMARY OF THE INVENTION
We have found novel compounds of the formula (I):
wherein:
R
1
and R
2
are independently hydrogen, C
1-8
alkyl, phenyl, and phenyl C
1-4
alkyl
R
3
is C
1-23
straight or branched or a cyclic alkyl or alkenyl; alkoxyalkyl; halogenated alkyl, phenyl, or benzyl; alkyl phenyl;
R
4
and R
5
are independently hydrogen or C
1-8
alkyl;
R
6
is hydrogen; C
1-8
alkyl; C
2-8
alkanoyl; phenyl C
1-4
alkyl, benzoyl wherein the phenyl moiety is optionally substituted by one or more halogen atoms or alkyl groups C
2-8
alkoxycarbonyl; CONHR
8
wherein R
8
is hydrogen, C
1-8
alkyl, phenyl, phenyl C
1-4
; phenyl C
2-4
alkyloxycarbonyl;
R
7
is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl;
X is O or NH and salts thereof; and the crop is selected from tomatoes, potatoes, cereals, grapes, melon, wheat and cucumber.
We have also found a novel method of protecting a crop against fungal diseases caused by fungi by applying to the crop or its locus a composition containing an effective amount of a compound of the formula (I).
DETAILED DESCRIPTION OF THE INVENTION
Alkyl as used herein refers to straight chains, branched and cyclic forms and preferably contain one to ten carbon atoms.
R
1
and R
2
are preferably independently hydrogen, methyl or phenyl, more preferably R
1
is hydrogen or methyl and R
2
is hydrogen.
R
3
is preferably C
1-12
straight or branched or a cyclic alkyl or alkenyl, phenyl, benzyl, or alkyl phenyl.
R
4
and R
5
are preferably independently hydrogen or C
1-4
alkyl, more preferably R
4
is hydrogen or methyl and R
5
is hydrogen.
R
6
is preferably hydrogen, C
1-5
alkyl; and most preferred hydrogen methyl.
R
7
is benzenesulfonyl or benzoyl optionally substituted by one or more halogens, alkyl groups, amino groups or alkoxy groups; or thiophene carbonyl.
Preferred compounds of the invention are:
D,L N-benzenesulfonyl-3-aminobutyranilide;
D,L-N-&bgr;-methylbenzoyl-3-aminobutyric acid n-octyl ester;
N-&bgr;-methylbenzoyl-3-aminobutyric acid sec butyl ester;
D,L-N-3,4-dichloro benzoyl-3-aminobutyric acid n-octyl ester;
D,L-N-4-chlorobenzoyl-3-aminobutyric acid-2-chloro ethyl ester,
D,L-N-benzensulfonyl-3-amino N-benzyl butyramide;
D,L-N-benzoyl-3-aminobutyric acid 2-chloroethyl ester:
N-&bgr;-methylbenzoyl--3-amiobutyric acid 1-methyl-1-pentyl ester;
D,L-N-benzenesulfonyl-3-aminobutyric acid, n-octyl ester;
N-benzenesulfonyl-3-aminobutyric acid-sec-butyl ester;
N-benzenesulfonyl-3-aminobutyric acid-1-methyl-i -butyl ester;
D,L N-4-methoxybenzoyl-3-aminobutyric acid heptyl ester
D,L N-3,5-dimethylbezoyl-3-aminobutyric acid heptyl ester
D,L N-2,6-difluorobenzoyl-3-aminobutyric acid heptyl ester
D,L N-4-tertbutylbenzoyl-3-aminobutyric acid heptyl ester
D,L N-4-methylbenzenesulfonyl-3-aminobutyric acid i-methylpentyl ester
D,L N-benzenesulfonyl-3-aminobutyric acid 3-phenylpropyl ester
D,L N-4-cholrobenzoyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-benzenesulfonyl-3-aminobutyric acid 2-(trichloromethyl)ethyl ester
D,L N-4-methylbenzenesulfonyl-3-aminobutyric 1-methylpropyll ester
D,L N-3,4-dimethylbezoyl-3-aminobutyric acid 1-methylbutyl ester
D,L N-3-methylbezoyl-3-aminobutyric acid heptyl ester
D,L N-3,5-dimethylbezoyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-2,6-dichlorobenzoyl-3-aminobutyric acid heptyl ester
D,L N-2,6-dichlorobenzoyl-3-aminobutyric acid 2-methylpentyl ester
D,L N-4-methylbenzoyl-3-aminobutyric acid 3-phenylpropyl ester
D,L N-3,5-dimethylbezoyl-3-aminobutyric acid 2-chloroethyl ester
D,L N-4-methoxybenzoyl-3-aminobutyric acid 2-chloroethyl ester
D,L N-benzoyl-3-aminobutyric acid 2-(trichloromethyl)ethyl ester
D,L N-4-cholrobenzoyl-3-aminobutyric acid heptyl ester
D,L N-benzenesulfonyl-3-aminobutyric acid 1-methyl-2-methoxyethyl ester
D,L N-2-methylbezoyl-3-aminobutyric acid heptyl ester
D,L N-4-methylbenzenesulfonyl-3-aminobutyric acid 2-bromoethyl ester
D,L N-4-methylbenzenesulfonyl-3-aminobutyric acid heptyl ester
D,L N-4-chlorobenzenesulfonyl-3-aminobutyric acid propyl ester
D,L N-4-methylbenzoyl-3-aminobutyric acid 2-(trichloromethyl)ethyl ester
D,L N-4-methylbenzoyl-3-aminobutyric acid cyclohexyl ester
D,L N-benzoyl-3-aminobutyric acid cyclohexyl ester
D,L N-benzenesulfonyl-3-aminobutyric acid cyclohexyl ester
D,L N-4-chlorobenzenesulfonyl-3-aminobutyric acid heptyl ester
D,L N— benzenesulfonyl-3-aminobutyric acid propyl ester
D,L N-benzoyl-3-aminobutyric acid 2-propenyl ester
D,L N-4-methylbenzoyl-3-aminobutyric acid 1-methylhexyl ester
D,L N-4-methylbenzoyl-3-aminobutyric acid 1-methyldecanyl ester
D,L N-3,4-dimethylbezoyl-3-aminobutyric acid heptyl ester
D,L N-4-methylbezoyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-2-methylaminobenzoyl-3-aminobutyric acid methyl ester.
D,L N-4-chlorobenzensulfonyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-benzensulphonyl-3-aminobutyric acid 3-phenylpropyl ester
D,L N-2-methylaminobenzoyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-benzensulfonyl-3-aminobutyric acid 3,5-dichlorophenyl ester
D,L N-4-2-thiophenebenzoyl-3-aminobutyric acid octyl ester
D,L N-4-2-thiophenebenzoyl-3-aminobutyric acid 1-methylpentyl ester
D,L N-3,4-dimethylbenzoyl-3-aminobutyric acid octyl ester
Production methods
The novel compounds encompassed by the present application are structurally related to known compounds and can be easily prepared by either derivatising the known compounds or by modifying the procedures for preparing the known compound, as required. These procedures will be apparent to those skilled in the art. The following procedures are illustrative.
Compounds of the formula (I)
wherein R
1
and R
2
and R
4
are as previously defined and R
3
represents hydorgen or C
1-8
alkyl can be obtained from &bgr;-aminobutyric acid.
To prepare compounds of formula (I) where R
6
and R
7
are as previously defined &bgr;-aminobutyric acid is reacted with NR
7
H
2
, wherein R
7
is as previously defined. Reactions of this type are described in the literature, e.g., by A. Zilkha and J. Rivilin, J. Org. Chem. 1957, 23, 94.
The present compounds were found to be effective against late blight in potato and tomatoes, powdery mildew in cereals, downy meldow in cucumber, melon and grapes.
The present compounds of this invention will t

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