Use of derivatives of N-phenl-3,4,5,6-tetrahydrophthalimide...

Details Use of derivatives of N-phenl-3,4,5,6-tetrahydrophthalimide... Use of derivatives of N-phenl-3,4,5,6-tetrahydrophthalimide...

1996-03-19

2002-04-16

Pak, John (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Abscission agent, defoliant, or desiccant

C504S284000, C504S286000

Reissue Patent

active

RE037664

ABSTRACT:

The present invention relates to the use of derivatives of N-phenyl-3,4,5,6-tetrahyrophthalimide of the general formulae I and/or II
where
R is hydrogen, fluorine or chlorine,
A is hydrogen, C
1
-C
4
cyanoalkyl or a group I-1 to I-11
R
1
is hydrogen, chlorine, bromine cyano or C
1
-C
6
-alkyl,
R
2
is hydrogen, C
1
-C
8
-alkyl,
C
1
-C
8
-alkenyl

C
2
-C
8-
alkenyl
, C
2
-C
4
-alkynyl, C
1
-C
4
-alkoxy-C
1
-C
4
-alkyl, C
1
-C
4
-alkylthio-C
1
-C
4
-alkyl, phenyl-C
1
-C
3
-alkyl or,
where X is NR
8

where Q is NR
8
, also C
1
-C
4
-hydroxy-alkyl, C
1
-C
4
-alkoxy, C
2
-C
4
-alkenyloxy, phenyl, phenyl substituted by halogen, C
1
-C
4
-alkyl or -alkoxy, C
1
-C
4
-haloalkyl or -haloalkoxy,
R
3
is hydrogen, C
1
-C
4
-alkyl, C
1
-C
4
-hydroxyalkyl, C
1
-C
4
-haloalkyl, C
1
-C
5
-cyanoalkyl, C
1
-C
4
-mercaptoalkyl, C
1
-C
4
-alkoxyalkyl, C
1
-C
4
-alkylthioalkyl, C
1
-C
4
-alkylcarbonyloxy-C
1
-C
4
-alkyl or C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylthioalkyl,
R
4
, R
5
and R
6
are each hydrogen or C
1
-C
3
-alkyl,
E is oxygen or methylene,
X is oxygen or sulfur,
Q is oxygen, sulfur or N
8
,
Y is oxygen, sulfur or CHR
4
,
n is 0 or 1,
Z is methylene, methyleneoxymethylene, methylenethiomethylene or ethenylene, R
7
is hydrogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxyalkyl, C
1
-C
6
-alkylthioalkyl or C
5
- or C
6
-cycloalkyl,
R
8
is C
1
-C
8
-alkyl, C
3
-,or C
4
-alkenyl, C
3
- or C
4
-alkynyl or C
1
-C
6
-alkoxyalkyl,
R
9
is hydrogen, chlorine, bromine, cyano, C-C
4
-alkyl, C
3
- or C
4
-alkenyl, C
3
- or C
4
-alkynyl, C
1
-C
6
-alkoxyalkyl, C
1
-C
6
-alkylthioalkyl or cyclohexylmethyl,
R
10
is hydrogen, halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
3
-alkoxycarbonyl or C
1
-C
4
-alkoxycarbonyl, or R
9
and
R
10
together form a C
4
- or C
5
-alkylene or C
4
- or C
5
-oxoalkylene group,
R
11
is C
1
-C
6
-alkyl, C
3
- or C
4
-alkenyl, C
3
- or C
4
-alkynyl or a group
 or —CH
2
C(CH
3
)
2
COOR
2
,
R
12
is hydrogen or cyano,
R
13
is hydrogen or C
1
-C
4
-alkoxycarbonyl,
R
14
is C
1
-C
4
-alkyl, C
3
- or C
4
-alkenyl, C
3
- or C
4
-alkynyl, C
1
-C
4
-alkylcarbonyl, C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkyl, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl,
R
15
is hydrogen, C
1
-C
4
-alkyl, C
3
- or C
4
-alkynyl, C
1
-C
4
-alkoxycarbonyl -C
1
-C
4
-alkyl or —N═C(CH
3
)
2
and
R
16
is hydrogen; C
1
-C
4
-alkyl, C
3
- or C
4
-alkenyl, C
3
- or C
4
-alkynyl, unsubstituted benzyl or benzyl which is, monosubstituted to trisubstituted by halogen or C
1
-C
4
-alkyl, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl,
for the desiccation and abscission of plant organs.
The present invention furthermore relates to a method for the desiccation and abscission of plant organs, in particular of the leaves, by means of the above-mentioned compounds I and II.
EP-A 207 894 discloses that specially substituted N-phenyl-3,4,5,6-tetrahydrophthalimides have selected herbicidal properties as well as a plant growth-regulating action. An example indicates the desiccant and defoliant action in cotton plants without specifying the active ingredients. The application rates are 0.6 and 1.2 kg/ha. Evidently no good results were obtained with 0.3 kg/ha.
The use of tetrahydrophthalimide derivatives as herbicides is described in a number of publications, for example in DE-A-36 03 789, DE-A-36 07 300, DE-A-30 13 162, DE-A-31 09 035, DE-A-35 33 440, EP-A-61 741, EP-A-83 055, EP-A-68 822, EP-A-236 916, GB-A-20 71 100, U.S. Pat. No. 3,878,224, JP 59/155 358 and JP 61/027 962. These publications do not disclose the use of the compounds as abscission agents for the controlled induction of the dropping of leaves, blossoms of fruit in crops, such as cotton, citrus fruit, olives, pomes and drupes, and their use as desiccants for drying out the visible parts in crops, for example potato, rape, sunflower and soybean.
There is considerable economic interest in both abscission agents and desiccants, for facilitating harvesting. Particularly in intensive cotton cultivation, the use of defoliants is essential for effective use of picking machines or harvesting the bolls. The commercial products used to date do not meet essential requirements in practice, for example rapid and lasting activity even under cooled temperature conditions, low application rates and no environmental pollution (toxicity, odor and flammability).
We have found that the N-phenyl-3,4,5,6-tetrahydrophthalimides defined at the outset have high activity with regard to the abscission and desiccation of plant organs. Their use has considerable advantages compared with known agents:
a) Their action is optimum even at low application rates of about 60-250 g/ha,
b) Their effect is much more complete at a comparable application rate and
c) Their action is much more reliable even at low temperatures.
In addition to their excellent action as defoliants, the compounds I and/or II have very good activity when they are used as desiccants for drying out the visible parts of crop plants, for example potatoes, sunflower, soybean and rape, in order to facilitate the harvesting process. Furthermore, they result in uniform ripening of the fruit to be harvested.
The compounds which are particularly preferred because of their activity are N-phenyl-3,4,5,6-tetrahydrophthalimides of the structure I, where R is fluorine or, in particular, hydrogen.
Preferred radicals A are the following groups:
where
Q is oxygen,
R
1
is H, Cl, Br, CN or C
1
-C
6
-alkyl, in particular C
1
-C
4
-alkyl, and R
2
is H, C
1
-C
8
-alkyl, in particular C
1
-C
4
-alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or isobutyl,
C
1
-C
8
-alkenyl

C
2
-C
8
-
alkenyl
, in particular
C
1
-C
4
-alkenyl
,
C
2
-C
4
-
alkenyl
, C
3
- or
C
4
alkynyl

C
4
alkynyl
,
C
1
-C
8
-C
4
-alkylthio-C
1
-C
4
-alkyl
,
C
1
-C
4
-
alkylthio
-
C
1
-C
4
-
alkyl
, C
1
-C
17
-aralkyl, for example phenylalkyl, such as benzyl or 2-phenylethyl, or C
3
-C
6
-cycloalkyl, in particular C
5
- or C
6
-cycloalkyl, such as cyclopentyl or cyclohexyl,
where X is O or S, n is 0 or 1, R
3
is H or C
1
-C
4
-alkyl as stated for R
2
, which may be substituted by hydroxyl, halogen, such as fluorine, chlorine or bromine, cyano, mercapto, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkyl-carbonyloxy or C
1
-C
4
-alkoxycarbonyl-C
1
-C
4
-alkylthio, and R
4
is hydrogen or C
1
-C
3
-alkyl,
OR
14
  
(
I-10
where R
14
is, in particular, tetrahydrofurfuryl, dihydropyranylmethyl, dihydrothiopyranylmethyl, tetrahydropyranylmethyl or tetrahydrothiopyranylmethyl.
The N-substituted tetrahydrophthalimides I are obtainable from 3,4,5,6-tetrahydrophthalic anhydride and appropriately substituted aniline derivatives, which can be prepared by reduction of the corresponding nitro compounds. As a rule, the reaction is carried out in an inert solvent at from 20° to 200° C., preferably from 40° to 50° C. Examples of suitable solvents are lower alkanecarboxylic acids, such as glacial acetic acid or propionic acid, or aprotic solvents, such as toluene or xylene, in the presence of acidic catalysts, for example aromatic sulfonic acids.
Cyanoalkyl-substituted N-phenyltetrahydrophthalimides are described in EP-A 68 822.
N-phenyltetrahydrophthalimides in which A is a group I-1 are disclosed in DE-A 36 03 789 (EP-A 240 659) or DE-A 37 24 399 (EP-A-300 387). They can also be prepared by reacting an aldehyde of the formula IV
with a phosphorane of the formula V
where Ar is unsubstituted or substituted phenyl at from −10° to 100° C. and in the presence of a solvent. The aldehydes of the general formula IV which are used as starting materials are obtainable in a simple manner by the methods described in German Patent Application 3815042.5 (0.Z. 0050/39993). The radical R of these compounds may be hydrogen or fluorine.
The phosphoranes V which are required for the preparation of the tetrahydrophthalimides and which are also referred to as phosphorylides are obtainable by methods kn

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