Novel N-(1-alkenyl)-chloroacetanilides as herbicides and plant growth regulators

N-(Alkenyl)-chloroacetanilides of the formula ##STR1## in which R.sup.1 represents a hydrogen atom or an alkyl group, PA1 R.sup.2 represents a hydrogen atom or an alkyl, alkoxy, alkoxyalkyl, hydroxyalkyl or benzyl group, PA1 R.sup.3 represents a hydrogen atom or an alkyl, alkenyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkylcarbonyl-alkyl, alkoxycarbonyl or alkoxycarbonylalkyl group, or PA1 R.sup.1 and R.sup.2, together with the C.dbd.C double bond, represent an optionally substituted mono-unsaturated or polyunsaturated ring which can also contain heteroatoms, or PA1 R.sup.2 and R.sup.3, together with the adjacent carbon atom, represent an optionally substituted, saturated or unsaturated ring which can also contain heteroatoms and/or a carbonyl group, or PA1 R.sup.2 and R.sup.3 together represent a radical of the formula ##STR2## wherein R.sup.6 represents a hydrogen atom or an alkyl group and PA1 R.sup.7 represents an alkyl or phenyl group and PA1 X.sup.1, X.sup.2 and X.sup.3 independently of one another represent a hydrogen or halogen atom or an alkyl group, which possess herbicidal and plant growth regulating properties.

The present invention relates to certain new 
N-(1-alkenyl)-chloroacetanilides, to a process for their use as herbicides 
and as plant growth regulators. 
It has already been disclosed that many chloroacetanilides possess 
herbicidal properties. Thus, for example, 
2,6-diethyl-N-methoxymethyl-chloroacetanilide can be used for combating 
weeds (see U.S. Pat. No. 3,442,945). However, the action of this compound 
is not always completely satisfactory and, in particular, its use as a 
selective herbicide is only possible to a limited extent in the case of 
many cultivated plants. 
The present invention now provides, as new compounds, 
N-(1-alkenyl)-chloroacetanilides of the general formula 
##STR3## 
in which R.sup.1 represents a hydrogen atom or an alkyl group, 
R.sup.2 represents a hydrogen atom or an alkyl, alkoxy, alkoxyalkyl, 
hydroxyalkyl or benzyl group, 
R.sup.3 represents a hydrogen atom or an alkyl, alkenyl, alkoxy, 
alkoxyalkyl, alkylcarbonyl, alkylcarbonyl-alkyl, alkoxycarbonyl or 
alkoxycarbonylalkyl group or 
R.sup.1 and R.sup.2, together with the C.dbd.C double bond, represent an 
optionally substituted monounsaturated or polyunsaturated ring which can 
also contain hetero-atoms and/or a carbonyl group, or 
R.sup.2 and R.sup.3, together with the adjacent carbon atom, represent an 
optionally substituted, saturated or unsaturated ring which can also 
contain heteroatoms, or 
R.sup.2 and R.sup.3 together represent a radical of the general formula 
##STR4## 
wherein R.sup.6 represents a hydrogen atom or an alkyl group and 
R.sup.7 represents an alkyl or phenyl group and 
X.sup.1, X.sup.2 and X.sup.3 independently of one another represent a 
hydrogen or halogen atom or an alkyl group. 
According to the present invention we provide a process for the production 
of a compound of the present invention, characterized in that an azine of 
the general formula 
##STR5## 
in which R.sup.1, X.sup.1, X.sup.2 and X.sup.3 have the meanings given 
above, 
R.sup.4 represents a hydrogen atom or an alkyl, alkoxy, alkoxyalkyl, 
hydroxyalkyl or benzyl group and 
R.sup.5 represents a hydrogen atom or an alkyl, alkenyl, alkoxy, 
alkoxyalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl or 
alkoxy-carbonylalkyl group, or 
R.sup.1 and R.sup.4, together with the adjacent C--C bond, represent an 
optionally substituted, saturated or unsaturated ring which can also 
contain heteroatoms and/or a carbonyl group, or 
R.sup.4 and R.sup.5, together with the adjacent carbon atom, represent an 
optionally substituted, saturated or unsaturated ring which can also 
contain heteroatoms, or 
R.sup.4 and R.sup.5 together represent a radical of the general formula 
##STR6## 
wherein R.sup.6 and R.sup.7 have the meanings given above, 
is reacted with a chloroacetyl halide of the general formula 
EQU Hal--CO--CH.sub.2 --Cl (III) 
in which 
Hal represents a chlorine or bromine atom, 
if appropriate in the presence of a diluent, and the resulting 
chloroacetanilide of the general formula 
##STR7## 
in which R.sup.1, R.sup.4, R.sup.5, X.sup.1, X.sup.2, X.sup.3 and Hal have 
the meanings given above, 
is subjected, without preliminary isolation, to an elimination of hydrogen 
halide, if appropriate in the presence of a base. 
In addition, it has been found that the compounds of the present invention 
have good herbicidal properties, in particular selective herbicidal 
properties. In addition, they are very suitable for use in regulating 
plant growth. 
Surprisingly, the compounds according to the present invention are more 
promising for use as selective agents for combating weeds, and have a 
comparably good general action against weeds, in comparison with the known 
2,6-diethyl-N-methoxymethylchloroacetanilide which is a similar compound 
chemically and with respect to its action. Furthermore, the compounds 
according to the invention surprisingly also possess a powerful plant 
growth-regulating activity. 
Preferred compounds according to the present invention are those in which 
R.sup.1 represents a hydrogen atom or a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms; 
R.sup.2 represents a hydrogen atom, a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon 
atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxyalkyl 
group having 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms 
in the alkoxy part, or a benzyl group; 
R.sup.3 represents a hydrogen atom, a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon 
atoms, an alkoxyalkyl group having 1 to 4 carbon atoms in the alkyl part 
and 1 to 4 carbon atoms in the alkoxy part, an alkylcarbonyl group having 
1 to 4 carbon atoms in the alkyl part, an alkylcarbonylalkyl group having 
1 to 4 carbon atoms in each alkyl part, an alkoxycarbonyl group having 1 
to 4 carbon atoms in the alkoxy part, an alkoxycarbonylalkyl group having 
1 to 4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the 
alkyl part or a straight-chain or branched alkenyl group having 2 to 6 
carbon atoms; or 
R.sup.1 and R.sup.2, together with the C.dbd.C double bond, represent an 
optionally monosubstituted or polysubstituted, mono-unsaturated or 
poly-unsaturated, 5-membered or 6-membered ring which can contain one or 
two hetero-atoms (the following being mentioned as examples of 
substituents: alkyl having 1 to 4 carbon atoms, halogen and hydroxy) 
and/or a carbonyl group, or 
R.sup.2 and R.sup.3, together with the adjacent carbon atom, represent an 
optionally monosubstituted or poly-substituted, saturated or unsaturated, 
5-membered or 6-membered ring which can contain one or two hetero-atoms 
(the following being mentioned as examples of substituents: alkyl having 1 
to 4 carbon atoms, halogen and hydroxy), or 
R.sup.2 and R.sup.3 together represent a radical of the general formula 
##STR8## 
wherein R.sup.6 represents a hydrogen atom or an alkyl group having 1 to 4 
carbon atoms and 
R.sup.7 represents an alkyl group having 1 to 4 carbon atoms or a phenyl 
group; 
X.sup.1, X.sup.2 and X.sup.3 independently of one another, represent a 
hydrogen, fluorine, chlorine or bromine atom or a straight-chain or 
branched alkyl group having 1 to 4 carbon atoms. 
Particularly preferred compounds of the present invention are those in 
which 
R.sup.1 represents a hydrogen atom or a methyl, ethyl or isopropyl group; 
R.sup.2 represents a hydrogen atom, or a methyl ethyl, isopropyl, methoxy, 
ethoxy, isopropoxy, methoxymethyl, ethoxymethyl, iso-hydroxypropyl or 
benzyl group; 
R.sup.3 represents a hydrogen atom or a methyl, ethyl, isopropyl, methoxy, 
ethoxy, isopropoxy, methoxymethyl, ethoxymethyl, methylcarbonyl, 
ethylcarbonyl, methylcarbonylmethyl, methoxycarbonyl, ethoxycarbonyl or 
methoxycarbonylmethyl group or a straight-chain or branched alkenyl group 
having 2 to 4 carbon atoms; or 
R.sup.1 and R.sup.2, together with the C.dbd.C double bond, represent a 
mono-unsaturated or poly-unsaturated, 5-membered or 6-membered ring which 
is optionally substituted by methyl, ethyl, hydroxyl and/or chlorine and 
which can contain one or two heteroatoms (such as oxygen, nitrogen and/or 
sulphur) and/or a carbonyl group, or 
R.sup.2 and R.sup.3, together with the adjacent carbon atom, represent a 
saturated or unsaturated, 5-membered or 6-membered ring which is 
optionally substituted by methyl, ethyl, hydroxy and/or chlorine and which 
can contain one or two hetero-atoms (such as oxygen, nitrogen and/or 
sulphur), or 
R.sup.2 and R.sup.3 together represent the radical of the general formula 
##STR9## 
wherein R.sup.6 represents a hydrogen atom or a methyl or ethyl group and 
R.sup.7 represents a methyl, ethyl or phenyl group; 
X.sup.1, X.sup.2 and X.sup.3, independently of one another represent a 
hydrogen, chlorine or fluorine atom or a methyl, ethyl, isopropyl, 
isobutyl, sec.-butyl, tert.-butyl group. 
If, for example, N-ethylidene-2,6-diethylaniline and chloroacetyl chloride 
are used as the starting materials, the course of the reaction, of the 
process according to the invention is illustrated by the following 
equation: 
##STR10## 
If, for example, N-(3-cyclohexenyl-methylidene)-2,6-dimethylaniline and 
chloroacetyl chloride are used as the starting materials, the course of 
the reaction of the process according to the invention is illustrated by 
the following equation: 
##STR11## 
If, for example, N-(cyclopentylidene)-2-ethyl-6-methylaniline and 
chloroacetyl chloride are used as the starting materials, the course of 
the reaction of the process according to the invention is illustrated by 
the following equation: 
##STR12## 
Preferred azines of formula (II) to be used as the starting materials for 
the reaction according to the invention are those in which 
R.sup.1, X.sup.1, X.sup.2 and X.sup.3 represent those radicals which have 
already been mentioned in connection with the description of the preferred 
compounds according to the invention, 
R.sup.4 represents a hydrogen atom, a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon 
atoms, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxyalkyl 
group having 1 to 4 carbon atoms in the alkyl part and 1 to 4 carbon atoms 
in the alkoxy part, or benzyl, 
R.sup.5 represents a hydrogen atom, a straight-chain or branched alkyl 
group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon 
atoms, an alkoxyalkyl group having 1 to 4 carbon atoms in the alkyl part 
and 1 to 4 carbon atoms in the alkoxy part, an alkylcarbonyl group having 
1 to 4 carbon atoms in the alkyl part, an alkylcarbonyl-alkyl group having 
1 to 4 carbon atoms in each alkyl part, an alkoxycarbonyl group having 1 
to 4 carbon atoms in the alkoxy part, an alkoxycarbonylalkyl having 1 to 
4 carbon atoms in the alkoxy part and 1 to 4 carbon atoms in the alkyl 
part, or a straight-chain or branched alkenyl group having 2 to 6 carbon 
atoms, or 
R.sup.1 and R.sup.4, together with the adjacent C--C bond, additionally 
represent an optionally monosubstituted or polysubstituted, saturated or 
unsaturated, 5-membered or 6-membered ring which can contain one or two 
hetero-atoms and/or a carbonyl group (the following being mentioned as 
examples of substituents: alkyl having 1 to 4 carbon atoms, halogen and 
hydroxyl), or 
R.sup.4 and R.sup.5, together with the adjacent monosubstituted or 
polysubstituted, saturated or unsaturated, 5-membered or 6-membered ring 
which can contain one or two hetero-atoms (the following being mentioned 
as examples of substituents: alkyl having 1 to 4 carbon atoms, halogen and 
hydroxyl), or 
R.sup.4 and R.sup.5 together also represent a radical of the general 
formula 
##STR13## 
wherein R.sup.6 represents a hydrogen atom or an alkyl group having 1 to 4 
carbon atoms and 
R.sup.7 represents an alkyl group having 1 to 4 carbon atoms or a phenyl 
group. 
Particularly preferred starting materials of formula (II) are those 
compounds, in which 
R.sup.1, X.sup.1, X.sup.2 and X.sup.3 have those meanings which have 
already been mentioned in connection with the description of the 
particularly preferred compounds according to the invention, 
R.sup.4 represents a hydrogen or a methyl, ethyl, isopropyl, methoxy, 
ethoxy, isopropoxy, methoxymethyl, ethoxymethyl, iso-hydroxypropyl or 
benzyl group; 
R.sup.5 represents a hydrogen atom or a methyl, ethyl, isopropyl, methoxy, 
ethoxy, isopropoxy, methoxymethyl, ethoxymethyl, methylcarbonyl, 
ethylcarbonyl, methylcarbonylmethyl, methoxycarbonyl, ethoxycarbonyl, or 
methoxycarbonylmethyl group or a straight-chain or branched alkenyl group 
having 2 to 4 carbon atoms; or 
R.sup.1 and R.sup.4, together with the adjacent C--C bond, represent a 
saturated or unsaturated 5-membered or 6-membered ring which is optionally 
substituted by methyl, ethyl, hydroxyl, and/or chlorine and which can 
contain one or two hetero-atoms (such as oxygen, nitrogen and/or sulphur) 
and/or a carbonyl group, or 
R.sup.4 and R.sup.5, together with the adjacent carbon atom, represent a 
saturated or unsaturated, 5-membered or 6-membered ring which is 
optionally substituted by methyl, ethyl, hydroxyl, and/or chlorine and 
which can contain one or two hetero-atoms (such as oxygen, nitrogen and/or 
sulphur), or 
R.sup.4 and R.sup.5 together represent a radical of the general formula 
##STR14## 
wherein R.sup.6 represents a hydrogen atom or a methyl, or ethyl group, 
and 
R.sup.7 represents a methyl, ethyl or phenyl group. 
Azines of the formula (II) are known and can be prepared in a simple manner 
by processes which are known in principle (see DE-OS (German Published 
Specification) No. 1,670,859 and DE-OS (German Published Specification) 
No. 3,011,084). Thus, the azines of the formula (II) can be synthesized by 
reacting an aniline of the general formula 
##STR15## 
in which X.sup.1, X.sup.2 and X.sup.3 have the meanings given above, 
with an aldehyde or ketone of the general formula 
##STR16## 
in which R.sup.1, R.sup.4 and R.sup.5 have the meanings given above, 
it being possible for the compounds of the formula (VI) optionally also to 
be present in the form of their acetals or ketals, if appropriate in the 
presence of an inert organic solvent (such as methylene chloride or 
toluene) and, if appropriate, in the presence of a basic or acid catalyst 
(such as dimethylbenzylamine or p-toluene-sulphonic acid) at a temperature 
between -10.degree. C. and +120.degree. C. (see also the preparative 
examples hereinbelow). 
Formula (III) gives the definition of the chloroacetyl halides further 
required as starting materials in the process according to the invention. 
The particular chloroacetyl halides are known. 
Suitable diluents for the process according to the invention are inert 
organic solvents. These preferably include ketones (such as acetone and 
methyl ethyl ketone), nitriles (such as acetonitrile), ethers (such as 
tetrahydrofuran or dioxane), esters (such as ethyl acetate) halogenated 
hydrocarbons (such as methylene chloride) and, especially aromatic 
hydrocarbons (such as benzene and toluene). 
In carrying out the first stage of the process according to the invention, 
the reaction temperatures can be varied within a relatively wide range. In 
general, the reaction is carried out at a temperature between -20.degree. 
and +150.degree. C., preferably between -20.degree. and +100.degree. C. 
The elimination of hydrogen halide in the second stage of the process 
according to the invention is effected in a generally customary and known 
manner. As a rule, the following procedure is followed: without 
preliminary isolation of the compounds of the formula (IV), the reaction 
mixture is heated or a base is added at the abovementioned temperatures. 
Any of the acid acceptors which are customarily suitable for reactions of 
this type can be employed as bases in this process. The following are 
preferably used: alkali metal carbonates (such as sodium and potassium 
carbonate or sodium bicarbonate), or lower tertiary alkylamines, 
aralkylamines, aromatic amines or cycloalkylamines, (such as 
triethylamine, dimethylbenzylamine, pyridine, 
1,5-diazabicyclo-[4.3.0]-non-5-ene (DBN) and 
1,8-diazabicyclo-[5.4.0]-undec-7-ene (DBU)). However, it is also possible 
to employ an appropriate excess of azine of the formula (II). 
In carrying out the elimination of hydrogen halide, the reaction 
temperatures can be varied in the same manner as has been described for 
the first stage of the process according to the invention. 
In carrying out the process according to the invention, the starting 
materials of the formulae (II) and (III) are preferably employed in 
equimolar quantities. The isolation of the end products is effected 
according to customary methods. 
The active compounds according to the invention influence plant growth and 
can therefore be used as defoliants, desiccants, agents for destroying 
broadleaved plants, germination inhibitors and, especially, as 
weed-killers. By "weeds" in the broadest sense there are meant plants 
growing in places where they are not desired. 
Whether the compounds according to the invention act as total herbicides or 
selective herbicides depends essentially on the amount used. 
The active compounds according to the present invention may be used, for 
example, to combat the following plants: 
dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, 
Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, 
Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, 
Cirsium, Carduus, Sonchus, Rorippa, Rotala, Lindernia, Lamium, Veronica, 
Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Solanum; 
and 
monocotyledon weeds of the genera Echinochloa, Setaria, Panicum, Digitaria, 
Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, 
Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, 
Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, 
Dactyloctenium, Agrostis, Alopecurus and Apera. 
The active compounds according to the present invention may be used, for 
example, as selective herbicides in the following cultures: 
dicotyledon cultures of the genera Gossypium, Glycine, Beta, Daucus, 
Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, 
Arachis, Brassica, Lactuca, Cucumis and Cucurbita; and 
monocotyledon cultures of the genera Oryza, Zea, Triticum, Hordeum, Avena, 
Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. 
However, the use of the active compounds according to the invention is in 
no way restricted to these genera but also embraces other plants, in the 
same way. 
Depending on the concentrations, the compounds can be used for the total 
combating of weeds, for example on industrial terrain and railway tracks 
and on paths and squares with or without trees. Equally, the compounds can 
be employed for combating weeds in perennial cultures, for example 
afforestations, decorative tree plantings, orchards, vineyards, citrus 
groves, nut orchards, banana plantations, coffee plantations, tea 
plantations, rubber plantations, oil palm plantations, cacao plantations, 
soft fruit plantings and hopfields, and for the selective combating of 
weeds in annual cultures. 
In addition to a very good general herbicidal action, the active compounds 
according to the invention exhibit a good toleration to useful plants. 
Thus, it is possible to selectively combat important graminaceous weeds in 
important crops of useful plants, such as cotton, corn, soy beans and 
beet. 
The compounds according to the present invention engage in the metabolism 
of plants and can therefore be employed as growth regulators. 
Experience to date of the mode of action of plant growth regulators has 
shown that an active compound can exert one or several different actions 
on plants. The actions of the compounds depend essentially on the point in 
time at which they are used, relative to the stage of development of the 
seed or of the plant, and on the amounts of active compound applied to the 
plants or their environment and the way in which the compounds are 
applied. In every case, growth regulators are intended positively to 
influence the crop plants in the desired manner. 
Plant growth-regulating compounds can be employed, for example, to inhibit 
vegetative plant growth. Such inhibition of growth is inter alia of 
economic interest in the case of grasses since, by repressing the growth 
of grass, it is possible, for example, to reduce the frequency of cutting 
the grass in ornamental gardens, parks and sports grounds, at verges, at 
airports or in fruit orchards. The inhibition of growth of herbaceous and 
woody plants at verges and in the vicinity of pipelines or overland lines 
or, quite generally, in areas in which heavy growth is undesired, is also 
of importance. 
The use of growth regulators to inhibit the growth in length of cereals is 
also important, since by shortening the stem the danger of lodging of the 
plants before harvesting is reduced or completely eliminated. Furthermore, 
growth regulators can strengthen the stem of cereals, which can counteract 
lodging. 
In the case of many crop plants, inhibition of the vegetative growth makes 
denser planting possible, so that greater yields per area of ground can be 
achieved. An advantage of the smaller plants thus produced is also that 
the crop can be worked and harvested more easily. 
Inhibition of the vegetative growth of plants can also lead to increases in 
yield, since the nutrients and assimilates benefit blossoming and fruit 
formation to a greater extent than they benefit the vegetative parts of 
plants. 
Promotion of vegetative growth can also frequently be achieved with growth 
regulators. This is of great utility if it is the vegetative parts of the 
plants which are harvested. Promoting the vegetative growth can, however, 
also simultaneously lead to a promotion of generative growth, since more 
assimilates are formed, so that more fruit, or larger fruit, is obtained. 
Increases in yield can in some cases be achieved by affecting the plant 
metabolism, without noticeable changes in vegetative growth. A change in 
the composition of plants, which in turn can lead to a better quality of 
the harvested products, can furthermore be achieved with growth 
regulators. Thus it is possible, for example, to increase the content of 
sugar in sugar beet, sugar cane, pineapples and citrus fruit or to 
increase the protein content in soy-beans or cereals. Using growth 
regulators it is also possible, for example, to inhibit the degradation of 
desired constituents, such as, for example, sugar in sugar beet or sugar 
cane, before or after harvesting. It is also possible favourably to 
influence the production or the efflux of secondary plant constituents. 
The stimulation of latex flux in rubber trees may be mentioned as an 
example. 
Parthenocarpous fruit can be formed under the influence of growth 
regulators. Furthermore, the gender of the flowers can be influenced. 
Sterility of the pollen can also be produced, which is of great importance 
in the breeding and preparation of hybrid seed. 
Branching of plants can be controlled by using growth regulators. On the 
one hand, by breaking the apical dominance, the development of side shoots 
can be promoted, which can be very desirable, especially in the 
cultivation of ornamental plants, also in connection with growth 
inhibition. On the other hand, however, it is also possible to inhibit the 
growth of side shoots. There is great interest in this action, for 
example, in the cultivation of tobacco or in the planting of tomatoes. 
The amount of leaf on plants can be controlled, under the influence of 
growth regulators, so that defoliation of the plants at a desired point in 
time is achieved. Such defoliation is of great importance in the 
mechanical harvesting of cotton, but is also of interest for facilitating 
harvesting in other crops, such as, for example, in viticulture. 
Defoliation of the plants can also be carried out to lower the 
transpiration of plants before they are transplanted. 
The shedding of fruit can also be controlled with growth regulators. On the 
one hand, it is possible to prevent premature shedding of fruit. However, 
on the other hand, shedding of fruit, or even the fall of blossom, can be 
promoted up to a certain degree (thinning out) in order to interrupt the 
alternance. By alternance there is understood the peculiarity of some 
varieties of fruit to produce very different yields from year to year, for 
endogenic reasons. Finally, using growth regulators it is possible to 
reduce the force required to detach the fruit at harvest time so as to 
permit mechanical harvesting or facilitate manual harvesting. 
Using growth regulators, it is furthermore possible to achieve an 
acceleration or retardation of ripening of the harvest product, before or 
after harvesting. This is of particular advantage, since it is thereby 
possible to achieve optimum adaptation to market requirements. 
Furthermore, growth regulators can at times improve the coloration of 
fruit. In addition, concentrating the ripening within a certain period of 
time is also achievable with the aid of growth regulators. This provides 
the preconditions for being able to carry out complete mechanical or 
manual harvesting in only a single pass, for example in the case of 
tobacco, tomatoes or coffee. 
Using growth regulators, it is furthermore possible to influence the latent 
period of seeds or buds of plants, so that the plants, such as, for 
example pineapple or ornamental plants in nurseries, germinate, shoot or 
blossom at a time at which they normally show no readiness to do so. 
Retarding the shooting of buds or the germination of seeds with the aid of 
growth regulators can be desirable in regions where frost is a hazard, in 
order to avoid damage by late frosts. 
Finally, the resistance of plants to frost, drought or a high salt content 
in the soil can be induced with growth regulators. Cultivation of plants 
in regions which are usually unsuitable for this purpose thereby becomes 
possible. 
The preferred time of application of the growth regulators depends on the 
climatic and vegetative circumstances. 
The foregoing description should not be taken as implying that each of the 
compounds can exhibit all of the described effects on plants. The effect 
exhibited by a compound in any particular set of circumstances must be 
determined empirically. 
The active compounds can be converted to the customary formulations, such 
as solutions, emulsions, suspensions, powders, foams, pastes, granules, 
aerosols, very fine capsules in polymeric substances and in coating 
compositions for seed, as well as ULV formulations. 
These formulations may be produced in known manner, for example by mixing 
the active compounds with extenders, that is to say liquid or liquefied 
gaseous or solid diluents or carriers, optionally with the use of 
surface-active agents, that is to say emulsifying agents and/or dispersing 
agents and/or foam-forming agents. In the case of the use of water as an 
extender, organic solvents can, for example, also be used as auxiliary 
solvents. 
As liquid diluents or carriers, especially solvents, there are suitable in 
the main, aromatic hydrocarbons, such as xylene, toluene or alkyl 
naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, 
such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic 
or alicyclic hydrocarbons, such as cyclohexane or paraffins, for example 
mineral oil fractions, alcohols, such as butanol or glycol as well as 
their ethers and esters, ketones, such as acetone, methyl ethyl ketone, 
methyl isobutyl ketone or cyclohexanone, or strongly polar solvents, such 
as dimethylformamide and dimethylsulphoxide, as well as water. 
By liquefied gaseous diluents or carriers are meant liquids which would be 
gaseous at normal temperature and under normal pressure, for example 
aerosol propellants, such as halogenated hydrocarbons as well as butane, 
propane, nitrogen and carbon dioxide. 
As solid carriers there may be used ground natural minerals, such as 
kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or 
diatomaceous earth, and ground synthetic minerals, such as 
highly-dispersed silicic acid, alumina and silicates. As solid carriers 
for granules there may be used crushed and fractionated natural rocks such 
as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic 
granules of inorganic and organic meals, and granules of organic material 
such as sawdust, coconut shells, corn cobs and tobacco stalks. 
As emulsifying and/or foam-forming agents there may be used non-ionic and 
anionic emulsifiers, such as polyoxyethylene-fatty acid esters, 
polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol 
ethers, alkyl sulphonates, alkyl sulphates, aryl sulphonates as well as 
albumin hydrolysis products. Dispersing agents include, for example, 
lignin sulphite waste liquors and methylcellulose. 
Adhesives such as carboxymethylcellulose and natural and synthetic polymers 
in the form of powders, granules or latices, such as gum arabic, polyvinyl 
alcohol and polyvinyl acetate, can be used in the formulations. 
It is possible to use colorants such as inorganic pigments, for example 
iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such 
as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, 
and trace nutrients, such as salts of iron, manganese, boron, copper, 
cobalt, molybdenum and zinc. 
The formulations in general contain from 0.1 to 95 percent by weight of 
active compound, preferably from 0.5 to 90 percent by weight. 
The active compounds according to the invention, as such or in the form of 
their formulations, can also be used, for combating weeds, as mixtures 
with known herbicides, finished formulations or tank mixing being 
possible. Mixtures with other known active compounds, such as fungicides, 
insecticides, acaricides, nematicides, bird repellents, growth factors, 
plant nutrients and agents which improve soil structure, are also 
possible. 
The active compounds can be used as such, in the form of their formulations 
or in the forms prepared therefrom by further dilution, such as 
ready-to-use solutions, suspensions, emulsions, powders, pastes and 
granules. They are used in the customary manner, for example by watering, 
spraying, atomizing, scattering or dusting. 
When the active compounds according to the invention are used as 
herbicides, the active compounds can be applied either before or after 
emergence of the plants. They are preferably applied before emergence of 
the plants, that is to say by the pre-emergence method. They can also be 
incorporated into the soil before sowing. 
The amount of active compound used can vary within a substantial range. It 
depends essentially on the nature of the desired effect. In general, the 
amounts used are between 0.05 and 10 kg of active compound per ha, 
preferably between 0.1 and 5 kg/ha, when the active compounds according to 
the invention are employed as herbicides; and between 0.01 and 50 kg of 
active compounds per ha, preferably between 0.05 and 10 kg/ha, when they 
are employed as plant growth regulators. 
When the compounds according to the invention are employed as plant growth 
regulators, the rule is that they are applied within a preferred period of 
time, the exact definition of which depends on the climatic and vegetative 
circumstances. 
The present invention also provides herbicidal or plant growth regulant 
composition containing as active ingredient a compound of the present 
invention in admixture with a solid or liquefied gaseous diluent or 
carrier or in admixture with a liquid diluent or carrier containing a 
surface-active agent. 
The present invention also provides a method of combating weeds which 
comprises applying to the weeds or to a habitat thereof, a compound of the 
present invention alone or in the form of a composition containing as 
active ingredient a compound of the present invention in admixture with a 
diluent or carrier. 
The present invention also provides a method of regulating the growth of 
plants which comprises applying to the plants, or to a habitat thereof, a 
compound of the present invention alone or in the form of a composition 
containing as active ingredient a compound of the present invention alone 
or in the form of a composition containing as active ingredient a compound 
of the present invention in admixture with a diluent or carrier. 
The present invention further provides crops protected from damage by weeds 
by being grown in areas in which immediately prior to and/or during the 
time of the growing a compound of the present invention was applied alone 
or in admixture with a diluent or carrier. 
The present invention further provides plants, the growth of which has been 
regulated by their being grown in areas in which immediately prior to 
and/or during the time of the growing a compound of the present invention 
was applied alone or in admixture with a diluent or carrier. 
It will be seen that the usual methods or providing a harvested crop may be 
improved by the present invention. 
When used in appropriate quantities, the compounds according to the 
invention also exhibit fungicidal action, in particular against Oomycetes 
or against cereal diseases. In this context, they disclose not only a 
protective action, but in some cases also systemic action. Thus, it is 
possible to protect plants against attack by fungi if the active compounds 
are fed, via the soil and the root or via the seed, to the parts of the 
plant which are above the soil.