Note: Descriptions are shown in the official language in which they were submitted.
- 1 -
The present invention relates to novel cyclohexe-
none derivatives, a process for their preparation, herbi-
cides which contain these compounds as active ingredients,and a method of controlling undes;rable plant growth.
DE-A-2 439 104 discloses that cyclohexenone deri-
vatives can be used for controlling undesirable grasses
;n broad-leavèd crops. Furthermore, DE-A-3 121 355, DE-A-
3 123 312 and DE-A-3 239 071 descr;be derivatives substi-
tuted by heterocyclic structures.
We have found nove~ cyclohexenone derivatives of
the formula I
oR4
/ N_~R1
R3 ~ C~ R2 ~I)
Q
~here R1 is 2-fluoroethyl, 2-chloroethyl, but-2-en-1-yl,
methoxymethyl or methoxyethyl, R2 is C1-C4-alkyl, pre-
ferably C2- or C3-alkyl, R3 is 2-isopropyl-1,3-di-
oxepan-S-yl, tetrahydrothiopyran-3-yl~ tetrahydropyran-3-
yl, tetrahydropyran-4-yl, 3-methyltetrahydropyran-4-yl,
pyrid-3-yl, tetrahydrofuran-3-yl or 4a, 7,8,8a-tetrahydro-
2H, SH-pyrano~4,3-b]pyran-3-yl, and R4 is hydrogen, C1-C20-
alkylcarbonyl, C2-C20-alkenylcarbonyl, which preferably
has one C-C double bond, or benzoyl which is unsubstitu-
ted or substituted by C1-Cg-alkyl, or is C1-C4-tr;alkyl-
s;lyl, C1-C4-alkylsulfonyl, phenylsulfonyl which is
unsubstituted or substituted by C1-C4-alkyl, or Cl-C4-
dialkylphosphono or C1-C4-dialkylthiophosphono, and
salts of these compounds.
,;,
5~
- la -
In particular, the invention provides such
a derivative where R4 is hydrogen and provides for use
of this compount in a process for the control of unwanted
plants.
The novel cyclohexenone derivatives have a
good herbicidal action, preferably against species from
the grass family (Gramineae).
The compounds of the formula I can occur in
a plurality of tautomeric fonms, all of which are embraced
.' /
/
/
.. . . . . ..
3~ 3
- 2 - o.Z. 0050/38036
the claim. Far example, the compounds in which R4 is hyd-
rogen can occur, inter alia, in the following tautomeric
forms:
lORl ~XoRl ~ o 1
The compound in which R1 is but-2-en-1-yl is
understood as meaning both the E and the Z isomer~
In formuLa I, R2 is, for example, methyl, ethyl,
n-propyl, isopropyl, n-butyl, sec-butyl, ;sobutyl or tert-
butyl, and R4 ;s, for example, hydrogen, acetyl, pro-
pionyl, acryloyl, butyryl, isobutyryl, p;valoyl, valeryl,
caproyl, capronyl, lauroyl, palmitoyl, stearoyl, oleoyl,
benzoyl, 4-methylben20yl, 4-he~ylbenzoyl, tr;methyls;lyl,
tr;ethyls;lyl, methylsulfonyl, ethylsulfonyl, benzoyl-
sulfonyl, 4-methylphenylsulfonyl, diethylphosphono or di-
ethylth;ophosphono.
Su;table salts of the compounds of the formula Iare those which can be used in agriculture, for example
the alkali metal salts, in particu~ar the potassium or
sodium salts, alkaline earth metal salts, in particular
calcium and magnesium salts, manganese, copper, zinc or
iron salts and ammonium, sulfonium and phosphonium salts.
The novel compounds of the formula I can be ob-
tained by first reacting a tricarbonyl compound of the for-
mula II
0
o R2
where R2 and R3 have the above meanings, with an ammonium
compound of the formula R10-NH3Y, where R1 has the above
meanings and Y is an anion, for example a halide such as
fluoride, chloride, bromide or iodide, carbonate or sulfate,
i ~313
.
- 3 - O.Z. 0053/38036
and then, where R4 is not hydrogen, reacting the product
with a compound R4X in which R4 has the above meanings,
with the exception of hydrogen, and X is a leaving group,
in the presence or absence of an inert soLvent.
The reaction with the ammonium compound is advan-
tageously carried out in the heterogeneous phase in an
inert diluent at from O to 80C or from 0C to the boil-
ing point of the reaction mixture in the presence of a
base. Examples of suitable bases are the carbonates, bi-
carbonates, acetates, alkanolates, hydroxides and oxides
of alkali metals and alkaline earth metals, in particular
of sodium, potassium, magnesium and calcium. Organic
bases, such as pyridine or tertiary amines, may also be
used.
Examples of suitable ;nert diluents for th;s reac-
tion step are dimethyl sulfoxide, alcohols, such as ~etha-
nol, ethanol or isopropanol, benzene, hydrocarbons and
chlorohydrocarbons, such as chloroform, d;chloroethane,
hexane or cyclohexane, carboxylates, such as ethyl acetate,
and ethers, such as dioxane or tetrahydrofuran.
The reaction is complete after a few hours. The
product can then be isolated by evaporating down the mix-
ture, adding water and extracting with a nonpolar solvent,
such as methylene chloride, and then distilling off the
solvent under reduced pressure.
Instead of an ammonium compound, the tricarbonyl
compounds of the formula II can first be reacted with a
hydroxylamine of the formula R10-NH2, in which R1 has
the above meanings, in an inert diluent at from 0C to the
boil;ng point of the reaction mixture, in particular from
15 to 70C. If desired, the hydroxylamine can be employed
in the form of an aqueous solution.
Examples of suitable solvents for this reaction
are alcohols, such as methanol, ethanol, isopropanol or
cyclohexanol, hydrocarbons and chlorohydrocarbons, such
as hexane, cyclohexane, methylene chloride, toluene or
dichloroethane, carboxylates, such as ethyl acetate,
i3
- 4 - O.Z. 0050/38036
nitriles, such as acetonitrile, and cyclic ethers, such
as tetrahydrofuran.
Where R4 in formula I is hydrogen, the end prod-
uct is already obtained after the reaction with the ammon-
ium compound or with the hydroxylamine.
However, where R4 in formula I is other thanhydrogen, the above reaction is foLLowed by a further re-
action with a compound of the formula R4X in which R4 has
the above meanings with the exception of hydrogen, and X
is a leaving group (eg. chlorine, bromine or hydroxyl).
This reaction step is a conventionaL esterifica-
tion or silylation reaction. Such reactions are gene-
ralLy carried out at from 0 to 150C, in the presence or
absence of an inert solvent (eg~ toluene or chlorobenzene)
and of an auxiliary base (eg. potassium carbonate).
The above alkali metal salts of the cyclohexenone
derivatives of the formula I can be obtained by treating
these compounds with sodium hydroxide or potassium hyd-
roxide in aqueous solution or in an organic solvent, such
as methanol, ethanol or acetone. Sodium alkanolates and
potassium alkanolates may also be used as bases.
The other metal salts, for example the manganese,
copper, zinc, iron, calcium and magnesium salts, can be
prepared from the sodium salts by reaction with the app-
ropriate metal chloride in aqueous solution. The ammonium,
sulfonium and phosphonium salts can be prepared by reac-
ting the novel compounds of the formula I with ammonium
or phosphonium hydroxides, if necessary in aqueous solu-
tion.
The tricarbonyl compounds of the formula II can
be prepared from cyclohexenones of the formula III, which
may occur in the tautomeric form IIIa
(I~I) (IlIi~
1~3S~l~
- 5 - O.Z. 0050/38036
by reaction with carboxylic anhydrides by a conventional
method (Tetrahedron Lett. 29 (1975), 2491).
It is also possible to prepare the tricarbonyl
compounds of the formula II via the enol ester inter-
S mediates. These are obtained in the reaction of the cyclo-
hexenones of the formula III (possibly as isomer mixtures)
and can be subjected to a rearrangement reaction in the
presence of an imidazole or pyridine derivative (JP-A-
36052/1979).
The compounds of the formula III are likewise ob-
tained by methods known from the literature, as shown ;n
the scheme below:
3~l3
- 6 - O. Z . 0050/38036
R 3-CHo
\
o / \ CR2tt:oo8)2
-C-~H3 / \ Pyrid~i~e
~ase
O O
R3--CH~CH-C-CH3 R3~ ~C~-c--OH
\ C~2(C00~1~3~2 ~ C83-O~
\ Cl~3OI~4 ,-
R3-CII-C~I-COOCH3
/H3 C CH2 COOCH3/~H3ODs
~ .'
r~ '
~13COOC
1 ) KOI~
~ 2 ) ~ICl
R3~
~~0
3~; l3
- 7 - O.Z. 0050/38036
The aldehydes of the general formula R3-CHo which
are shown in the above scheme are obtainable by conven-
tional methods, for example by oxidation of the correspond-
ing alcohols, reduction of carbo%ylic acid derivatives or
S hydroformylation of olefins.
The Examples which follow illustrate the prepara-
tion of the novel cyclohexenone derivatives. Parts by
weight bear the same relation to parts by volume as that
of the kilogram to the liter.
The 1H NMR spectra were recorded in deuterochloro-
form as solvent, with tetramethyls;lane as the internal
nal standard. The 1H chemical shifts are stated as ~ppm]
in each case. The following abbreviations are used to
describe the signal structure:
s ~ s;nglet, d - doublet, t = tr;plet, q = quartet, m =
multiplet ~strongest s;gnal).
In the Examples, but-2-en-l-yl ;s abbreviated to
2-butenyl. The ;somer form ;s spec;f;ed ;n each case.
EXAMPLE 1
7.3 parts by we;ght of 2-acetyl-5-(3-tetrahydro-
th;opyranyl)-cyclohexane-1,3-d;one, 3.6 parts by weight
of 2-butenyloxyammon;um chloride and 2.4 parts by weight
of sodium bicarbonate in 100 parts by volume of methanol
were st;rred for 16 hours at room temperature. The sol-
vent was evaporated off under reduced pressure, the resi-
due was stirred with a mixture of 50 parts by volume of
water and 50 parts by volume of d;chloromethane, and the
aqueous phase was extracted once with 50 parts by valume
of dichloromethane. The combined organic phases were
washed with water and dr;ed over sod;um sulfate, and the
solvent was d;st;lled off under reduced pressure. 2-~1-
(2-butenyloxyimino)-ethyl]-3-hydroxy-5-(3-tetrahydrothio-
pyranyl)-cyclohex-2-en-1-one was obtained as a solid of
melt;ng point 65C (compound No. 2).
EXAMPLE 2
86 parts by weight of 2-butyryl-5-(3-tetrahydro-
thiopyranyl)-cyclohexane-1,3-dione and Z.6 parts by weight
.
l~r`~S:l~
- 8 - O.Z. 0050/38036
of 2-butenyloxyamine in dichloromethane were stirred for
16 hours at room temperature. The solution was washed
with 5% strength by weight hydrochloric acid and water
and dried over sodium sulfate, and the solvent was dis-
tilled off under reduced pressure. 2-[1-(2-3utenyloxy-
imino)-butyl]-3-hydroxy-5-(3-tetrahydrothiopyranyL)-cyclo-
hex-2-en-1-one was obtained in the form of an oil (com-
pound No. 14).
EXAMPLE 3
S parts by weight of 2-butyryl-5-(tetrahydrothio-
pyran-3-yl)-cyclohexane-1,3-dione, 2.31 parts by weight
of 2-fluoroethoxyammonium chloride and 1.68 parts by
weight of sodium bicarbonate in 100 parts by volume of
methanol were stirred for 16 hours at room temperature.
The solvent was distilled off under reduced pressure,
the residue was taken up with dichloromethane, and water
was added to the solution in a ratio of 1:1. The aqueous
phase was separated off and extracted with d;chloromethane.
The combined organic phases were dried over sodium sul-
fate and concentrated under reduced pressure. 5.3 parts(85%) of 2-~1-(2-fluoroethoximino)-butyl]-3-hydroxy-5-
(tetrahydrothiopyran-3-yl)-cyclohex-2-en-1-one were ob-
tained as a pale yellow oil (compound No. 13).
Other cyclohexenone derivatives are listed in
Tables 1 and 2 and are prepared in a similar manner.
In Table 1, R4 is hydrogen.
3513
- 9 - 0 . Z . 0050/38036
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- 15 - 0. Z. O0S0/38036
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- 16 - 0. Z . 0050/3~036
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.13
- 17 - O.Z. 0~50/38036
The cyclohexenone derivatlves of the formula I may be
applied for instance in the form of directly sprayable
solutions, powders, suspensions (including high-percentage
aqueous, oily or other suspensions), dispersions, emulsions,
05 oil dispersions, pastes, dusts, broadcasting agents, or
granules by spraying, atomizing, dusting, broadcasting or
watering. The forms of application depend entirely on the
purpose for which the agents are being used, but they must
ensure as fine a distribution of the active ingredients
according to the invention as possible.
For the preparation of solutions, emulsions, pastes
and oil dispersions to be sprayed direck, mineral oil frac-
tions of medium to high boiling point, such as kerosene or
diesel oil, further coal-tar oils, and oils of vegetable or
lS animal origin, aliphatic, cyclic and aromatic hydrocarbons
such as benzene, toluene, xylene, paraffin, tetrahydro-
naphthalene, alkylated naphthalenes and their derivatives
such as methanol, ethanol, propanol, butanol, chloroform,
carbon tetrachloride, cyclohexanol, cyclohexanone, chloro-
benzene, isophorone, etc., and strongly polar solvents suchas dimethylformamide, dimethyl sulfoxide, N-methyl-
pyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion con-
centrates, pastes, oil dispersions, wettable powders or
water-dispersible granules by adding water. To prepare
emulsions, pastes and oil dispersions the ingredients as
such or dissolved in an oil or solvent may be homogenized
in water by means of wetting or dispersing agents,
adherents or emulsifiers. Concentrates which are suitable
for dilution with water may be prepared from active in-
gredient, wetting agent, adherent, emulsifying or
dispersing agent and possibly solvent or oil.
Examples of surfactants are: alkali metal, alkaline
earth metal and ammonium salts of ligninsulfonic acid,
naphthalenesulfonic acids, phenolsulfonic acids, alkylaryl
sulfonates, alkyl sulfates, and alkyl sulfonates, alkali
?3S:~3
- 18 - O.Z. 0050/38036
metal and alkaline earth metal salts of dibutylnaphthalene-
sulfonic acid, lauryl ether sulfate, fatty alcohol sul-
fates, alkali metal and alkaline earth metal salts of fatty
acids, salts of sulfated hexadecanols, heptadecanols, and
05 octadecanols, salts of sulfated fatty alcohol glycol
ethers, condensation products of sulfonated naphthalene and
naphthalene derivatives with formaldehyde, condensation
products of naphthalene or naphthalenesulfonic acids with
phenol and formaldehyde, polyoxyethylene octylphenol
ethers, ethoxylated isooctylphenol, ethoxylated octylphenol
and ethoxylated nonylphenol, alkylphenol polyglycol ethers,
tributylphenyl polyglycol ethers, alkylaryl polyether
alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide
condensates, ethoxylated castor oil, polyoxyethylene alkyl
ethers, ethoxylated polyoxypropylene, lauryl alcohol poly-
glycol ether acetal, sorbitol esters, lignin, sulEite waste
li~uors and methyl cellulose.
Powders, dusts and broadcasting agents may be prepared
by mixing or grinding the active ingredients with a solid
carrier.
Granules, e.g., coated, impregnated or homogeneous gra-
nules, may be prepared by bonding the active ingredients to
solid carriers. Examples o~ solid carriers are mineral
earths such as 9ilicic acid, silica gels, silicates, talc,
kaolin, attapulgus clay, limestone, lime, chalk, bole,
loess, clay, dolomite, diatomaceous earth, calcium sulfate,
magnesium sulfate, magnesium oxide, ground plastics,
fertilizers such as ammonium sulfate, ammonium phosphate,
ammonium nitrate, and ureas, and vegetable products such as
grain flours, bark meal, wood meal, and nutshell meal,
cellulosic powders, etc.
The formulations contain from O.l to 9S, and prefer-
ably 0.5 to 9O, ~; by weight of active ingredient.
~t~ ,13
- 19 - O.Z. 0050/38036
Examples of formulations are given below.
I. 90 parts by weight of compound no. 134 is mixed
with 10 parts by weight of N-methyl-alpha-pyrrolidone. A
05 mixture is obtained which is suitable for application in
the form of very fine drops.
II. 20 parts by weight of compound no. 50 is dis-
solved in a mixture consisting of 80 parts by weight of
xylene, 10 parts by weight of the adduct of 8 to 10 moles
of ethylene oxide and 1 mole of oleic acid-N-monoethanol-
amide, 5 parts by weight of the calcium salt of dodecyl-
benzenesulfonic acid, and 5 parts by weight of the adduct
of 40 moles of ethylene oxide and 1 mole of castor oi:L. By
pouring the solution into 100,000 parts by weight of water
and uniormly distributing it therein, an aqueou~ disper-
sion i~ obtained containing 0.02% by weight oE the active
ingredient.
III. 20 parts by weight of compound no. 2 is dis-
solved in a mixture consisting of 40 parts by weight of
cyclohexanone, 30 parts by weight of isobutanol, 20 parts
by weight of the adduct of 7 moles of ethylene oxide and
1 mole of isooctylphenol, and 10 parts by weight of the
adduct of 40 moles of ethylene oxide and 1 mole of castor
oil. By pouring the solution into 100,000 parts by weight
of water and finely distributing it therein, an aqueous
dispersion is obtained containing 0.02~ by weight of the
active ingredient.
IV. 20 parts by weight of compound no. 104 is dis-
solved in a mixture consisting of 25 parts by weight of
cyclohexanone, 65 parts by weight of a mineral oil fraction
having a boiling point between 210 and 280C, and 10 parts
by weight of the adduct of 40 moles of ethylene oxide and
1 mole of castor oil. By pouring the solution into
100,000 parts by weight of water and uniformly distributing
it therein, an aqueous dispersion is obtained containing
0.02~; by weight of the active ingredient.
- 20 - o.z. 0050/38036
V. 20 parts by weight of compound no. 14 is well
mixed with 3 parts by weight of the sodium salt of diiso-
butylnaphthalene-alpha-sulfonic acid, 17 parts by weight of
the sodium salt of a lignin-sulfonic acid obtained from a
05 sulfite waste liquor, and 60 parts by weight of powdered
silica gel, and triturated in a hammer mill. By uniformly
distributing the mixture in 20,000 parts by weight of
water, a spray liquor is obtained containing O.l~i by weight
of the active ingredient.
VI. 3 parts by weight of compound no. 122 is
intimately mixed with 97 parts by weight of particulate
kaolin. ~ dust is obtained containing 3~, by weight of the
active ingredient.
VII. 30 parts by weight of compound no. 2 is
intimately mixed with a mixture consisting of 92 parts by
weight of powdered silica gel and 8 parts by weight oE
par~fin oil which has been sprayed onto the surface o~
this silica gel. A Eormulation of the active ingredient is
obtained having good adherence.
VIII. 20 parts by weight of compound no. 50 is
intimately mixed with 2 parts by weight of the calcium salt
of dodecylbenzenesulfonic acid, 8 parts by weight of a
fatty alcohol polyglycol ether, 2 parts by weight of the
sodium salt of a phenolsulfonic acid-urea-formaldehyde
condensate and 68 parts by weight of a paraffinic mineral
oil. A stable oily dispersion is obtained.
IX. 40 parts by weight of compound no. 2 is dissolved
in 60 parts by weight of a mixture consisting of 93 wt~. of
xylene and 7 wt~ of the adduct of 8 moles of ethylene oxide
and 1 mole of nonyl phenol. A solution is obtained contain-
ing 40 wt~ of active ingredient.
The novel herbicides exhibit a good herbicidal action
especially on Gramineae species. They are tolerated by, and
are thus selective in, broadleaved crops and monocotyledons
not belonging to the Gramineae family. Some of the novel
compounds also have a herbicidal action on broadleaved
plants, and some are suitable for non-selective control or
suppression of unwanted vegetation.
3~:13
- 21 - O.Z. 0050/38036
The active ingredients may be applied pre- or post-
emergence. If certain crop plants tolerate the active
ingredients less well, application techniques may be used
in which the herbicidal agents are sprayed from suitable
05 equipment in such a manner that the leaves of sensitive
crop plants are if possible not touched, and the agents
reach the soil or the unwanted plants growing beneath the
crop plants (post-directed, lay-by treatment).
The amount of active ingredient applied depends on the
time of the year, the plants to be combated and their
growth stage, and varies from 0.015 to 3 kg/ha, but is
preferably from 0.05 to 0.5 kg/ha.
The action of the cyclohexenone derivatives of the
formula I on plant growth is demonstrated in greenhouse
experiment~.
The vessels emplo~ed were plastic Elowerpots having a
volume o 300 cm3, and which were filled with a sandy loam
containing about 1.5~ humus. The seeds of the test plants
were sown shallow, and separately, according to species.
For the preemergence treatment, the active ingredients were
applied to the surface of the soil immediately after the
seeds had been sown. The compounds were emulsified or sus-
pended in water as vehicle, and sprayed through finely
distributing nozzles. The application rate was 3.0 kg of
active ingredient per hectare.
After the agents had been applied, the vessels were
lightly sprinkler-irrigated to induce germination and
growth. Transparent plastic covers were then placed on the
vessels until the plants had taken root. The cover ensured
uniform germination of the plants, insofar as this was not
impaired by the active ingredients.
For the postemergence treatment, the plants were first
grown in the vessels to a height of from 3 to 15 cm, depend-
ing on growth form, before being treated. The soybean
plants were grown in a peat-enriched substrate. For this
treatment, either plants which had been sown directly in
the pots and grown there were selected, or plants which had
- 22 - o.Z. 0050/38036
been grown from seedlings and were transplanted to the pots
a few days before treatment. The application rates for
postemergence treatment were 0.015 to 3 kg of active ingre-
dients per hectare. No covers were placed on the vessels in
05 this method.
The pots were set up in the greenhouse - species from
warmer areas at from 20 to 35C, and species from moder-
ate climates at lO to 25C. The experiments were run for 2
to 4 weeks. During this period, the plants were tended and
their reactions to the various treatments assessed. The
scale used for assessment was O to lOO, O denoting no
damage or normal emergence, and lOO denoting nonemergence
or complete destruction of at least the visible plant
parts.
The plants used in the e~periments were Alepecurus
myosuroides, Avena fatua, ~eta vulgaris, Centaurea cyanus,
Digitaria sanguinalis, Echinochloa crus-galli, Gl~cine
max., Hordium vulgare, Ipomoea spp., Mercurialis annua,
Oryza sativa, Setaria italica, Sinapis alba, Sorghum
bicolor, Triticum aestivum and Zea mays.
The herbicidal action of active ingredients nos. 134,
122, 50 and 104 selected by way of example on common grassy
weeds and volunteer plants is far superior to that of
closely related chemical derivatives. For comparison pur-
poses, herbicides were used which contained active ingre-
dients disclosed in DE-A-3,34~,265, DE-A-3,239,071,
DE-A-3,123,312 and DE-A-3,121,355.
For example compounds nos. 2 and 14, applied at a rate
of 3 kg/ha, are suitable for combatting unwanted grassy
vegetation in boradleaved crops such as soybeans and sugar-
beets, without appreciably influencing them. They have a
greater herbicidal action than comparable prior art com-
pounds disclosed in DE-A-3,121,355.
Compound no. 2 selected by way of example demonstrates
the possibility of using the novel compounds for suppressing
unwanted broadleaved vegetation. A far better herbicidal
action is achieved both pre- and postemergence than with
prior art active ingredients.
,
- 23 - O.Z. 0~50/38036
Compared with prior art compounds known from
British 2,137,200 and EP-125,094, for instance compound
no. 49 has, at a low application rate, a far greater
herbicidal action on unwanted grasses and volunteer wheat,
05 and is excellently tolerated by soybeans.
Compounds nos. 8, 26 and 62 are suitable even at low
application rates for combatting a broad spectrum of
unwanted grassy plants without damaging soybeans.
In view of the number of weeds which can be combatted,
the tolerance of the novel compounds by crop plants or the
desired influcence on growth, and in view of the numerous
application methods possible, the compounds according to
the invention may be used in a large number of crops
example are given below:
15 Botanical name Common name
Allium cepa onions
Ananas comosus pineapples
Arachis hypogaea peanuts (groundnuts)
20 Asparagus officinalis asparagus
Beta vulgaris spp. altissima sugarbeets
Beta vulgaris spp. rapa fodder beets
Beta vulgaris spp. esculenta table beets, red beets
Brassica napus var. napus rapeseed
25 Brassica napus var. napobrassica swedes
Brassica napus var. rapa turnips
Brassica rapa var. silvestris
Camellia sinensis tea plants
Carthamus tinctorius safflower
30 Carya illinoinensis pecan trees
Citrus limon lemons
Citrus maxima grapefruits
Citrus reticulata mandarins
Citrus sinensis orange trees
35 Coffea arabica (Coffea canephora,
Coffea liberica) coffee plants
Cucumis melo melons
Cucumis sativus cucumbers
3~13
- 24 - O.Z. 0050/38036
Botanical name Common name
Cynodon dactylon Bermudagrass
Daucus carota carrots
05 Elais guineensis oil palms
Fragaria vesca strawberries
Glycine max soybeans
Gossypium hirsutum
(Gossypium arboreum cotton
lO Gossypium herbaceum
Gossypium vitifolium)
Helianthus annuus sunflowers
Helianthus tuberosus Jerusalem artichoke
Hevea brasiliensis rubber plants
15 Humulus lupulus hops
Ipomoea batatas sweet potatoes
Juglans regia walnut trees
Lactuca sativa lettuce
Lens culinaris lentils
20 Linum usitatissimum flax
Lycopersicon lycopersicum tomatoes
Malus spp. apple trees
Manihot esculenta cassava
Medicago sativa alfalfa (lucerne)
25 Mentha piperita peppermint
Musa spp. banana plants
Nicothiana tabacum tobacco
(N. rustica)
Olea europaea olive trees
30 Phaseolus lunatus limabeans
Phaseolus mungo mungbeans
Phaseolus vulgar~s snapbeans, green beans,
dry beans
Petroselinum crispum parsley
spp. tuberosum
Picea abies Norway spruce
Abies alba fir trees
Pinus spp. pine trees
- 25 - O.Z. 0050/38036
Botanical name Common name
Pisum sativum English peas
Prunus avium cherxy trees
OS Prunus domestica plum trees
Prunus dulcis almond trees
Prunus persica peach trees
Pyrus communis pear trees
Ribes sylvestre redcurrants
~O Ribes uva-crispa gooseberries
Ricinus communis castor-oil plants
Saccharum officinarum sugar cane
Secale cereale rye
Sesamum indicum sesame
15 Solanum tuberosum Irish potatoes
Spinacia oleracea spinach
Theobroma cacao cacao plants
Trifolium pratense red clover
Triticum aestivum wheat
20 Vaccinium corymbosum blueberries
Vaccinium vitis-idaea cranberries
Vicia faba tick beans
Vigna sinensis (V. unguiculata) cow peas
Vitis vinifera grapes
25 Zea mays Indian corn, sweet
corn, maize
_
To increase the spectrum of action and to achieve
synergistic effects, the cyclohexenone derivatives of the
formula I may be mixed and applied together with numerous
representatives of other herbicidal or growth-regulating
active ingredient groups. Examples of suitable mixture
components are diazines, 4H-3,1-benzoxazine derivatives,
benzothiadiazinones, 2,6-dinitroanilines, N-phenyl-
carbamates, thiolcarbamates, halocarboxylic acids,
triazines, amides, ureas, triazinones, uracils, benzofuran
derivatives, quinolinecarboxylic acids, etc.
S~3
- 26 - O.Z. 0050/38036
It may also be useful to apply the compounds of the
formula I, either alone or in combination with other
herbicldes, in admixture with other crop protection agents,
e.g., agents for combatting pests or phytopathogenic fungi
05 or bacteria. The compounds may also be mixed with solutions
of mineral salts used to remedy nutritional or trace
element deficiencies. Non-phytotoxic oils and oil
concentrates may also be added.
