Note: Descriptions are shown in the official language in which they were submitted.
I
- I 0050/3728~
Cyclohexenone derivatives, their preparation and their
use for controlling undesirable plant growth
The present invention relates to cyclohexenone
derivatives, processes for their manufacture herbicides which contain
these compounds as active ingredients, and a method for controlling
undesirable plant growth
It has been disclosed that cyclohexenone derive-
toes can be used for controlling undesirable grasses in
broad-leaved crops (DE-A-2 439 104). Moreover, DE-A-
3 032 973 discloses derivatives Shea are cycloatkeny~-
substituted in the 5-position and which likewise possess
herb;cidal activity.
We have found that cyclohexenone derivatives of
the formula I
OH
A ~-~R3
I
Al D
where A is a cycloaLkyl radical of 5 to 12 rung members
which us fused with one or two ox;rane or thrown
rungs, is unsubstituted or substituted my not more than
four methyl groups and is bridged with an alkaline chain
of not more than 3 carbon atoms, R1 is hydrogen, moth-
oxycarbonyl or cyan, preferably hydrogen, R2 is alkyd
of 1 to carbon atoms and R3 us alkyd of 1 to 3 carbon
atoms alkenyl of 3 or 4 carbon atoms, haloalkenyl of 3
or 4 carbon atoms Shea has 1, Z or 3 halogen substitu-
entice or propargyl, and salts of these compounds have a
good herb;c;dal action preferably against species from
the grass foamily (Grumman). They have a selective
action in broad-leaved crops and in monocotyledon crops
which do not belong to the Rumania
The compounds of the formula I can occur in a
,; -`' , .`
- 2 - O . Z . SUE
plurality of forms all of which are embraced by the
c lams:
Jo Nut DRY Jo N O R 3
A {I= A
R I/ \ R R 1 D
A -.~ C A C
Al DO
In formula I, A is a cycloalkyl radical having S
to 12, preferably 5 to 8, rung members which is Fused
with one or two oxirane or thrown rings, is unsub-
statewide or substituted by not more than four methyl
groups and is bridged with an alkaline chain Do not more
than 3 carbon atoms, ego epoxycyclopentyl, epoxycyclo-
Huxley, epoxycycluheptyl, epoxycycLooctyl, epoxycyclo-
dodecyl, d;epoxycyclododecyl, epoxymethylcyclopentyl,
d;methylepoxycyclopentyl, epoxymethylcyclohexyl,
dimethylepoxycyclohexyl, epoxytr;methylcyclohexyl,
epoxytetramethylcyclohexyl, epoxybicycloheptyl, diepoxy-
trimethylcyclohexyl, epoxydimethylbicycloheptyl, en;-
thiocyclopentyl~ epith;ocyclohexyl or epithiobicyclo-
hotly. 3,4 Epoxycyclopentyl is particularly preferred.
In formula It I is striation or branched
~lkyl of 1 to 4, preferably 2 or 3, carbon atoms, to.
methyl, ethyl, nopropyl~ isopropyl, n-butyl, sec.-butyl,
i sobuty l or left buy l .
In formula I, R3 is propargyl, alkyd of 1 to 3
carbon atoms alkenyl of 3 or 4 carbon atoms or halo-
alkenyl of 3 or 4 carbon atoms which may contain not
I
- 3 - OOZE. 0~50/3728~
more than three halogen substituents, ego methyl ethyl,
n-propyl~ isopropyl, n-butyl~ sec. bottle, isobutyl,
tert~-butyl, allele 3 chloroprop-2-enyl, 2-chloroprop~
2-enyl, 1,3-dichloroprop 2~enyl or 2,3,3-trichloroprop-
2-enyl.
Suitable salts of the compounds of the formula I
are those which can be used in agriculture for example
the alkali metal salts, in particular the potassium or
sodium salts, alkaline earth metal salts, in particular
calcium, magnesium or barium salts, manganese, copper,
zinc and iron salts, and ammonium, sulfonium and pros-
phoneme salts.
The compounds of the formula I can be obtained
by reacting a tricarbonyl compound of the formula II
o
O
\ C
A r \ R2 IT
I
R 0
where A, R1 and R2 have the above meanings, with a
hydroxylam;ne derivative R30-NH3Y, where R3 has the above
meaning an Y is an anion.
The reaction is advantageously carried out in
the heterogeneous phase in an inert delineate at From û Jo
B0C or from 0C to the boiling point of the reaction
mixture in the presence of a base. Examples of suit
able bases are carbonates, bicarbonates, acetates, Alcoa
hilts, hydroxides or oxides of alkali metals or
Z5 alkaline earth metal, in particular those of sodium,
potassium, magnesium and calcium. It is also possible
to use organic bases, such as pardon or tertiary
ammonias
Examples of suitable delineates are dim ethyl sulk
oxide, alcohols, such as methanol, ethanol or
I
- 4 - OOZE. 0050/37Z80
isopropanol~ Bunsen, hydrocarbons and chLorohydro-
carbons, such as chloroform, dichloroethane, hexane or
cyclohexane, esters, such as ethyl acetate, and cyclic
ethers, such as Dixon or tetrahydrofuran. Mixtures of
these delineates may also be used.
The reaction is complete after a few hours, and
the product can then be isolated by evaporating down the
mixture, adding water and extracting with a non-polar
solvent, such as ethylene chloride, and distilling off
the solvent under reduced pressure.
The compounds of the formula I may furthermore be
obtained by reacting a compound of the formula II with a
hydroxylamine of the formula Ryan where R3 has the
above meanings, on an inert delineate at from 0C to the
boiling point of the reaction mixture, in particular from
15 to kiwi If necessary, the hydroxylamine can be
employed in aqueous solution.
Examples of suitable delineates for this reaction
are alcohols such as methanol, ethanol, ;sopropanol or
I cyclohexanol, hydrocarbons and chlorohydrocarbons, such
as hexane, cyclohexane, ethylene chloride, Tulane or
dichloroethane, esters, such as ethyl acetate, nitrites,
such as acetonitrile, and cyclic ethers, such as twitter
hydrofuran.
The alkali metal salts of the compounds of the
formula I can be obtained by treating these compounds
with sodium hydroxide or potassium hydroxide in aqueous
solution or in an organic solvent such as methanol,
ethanol or acetone Sodium alcoholates and potassium
alcoholates may also serve as bases.
The other metal salts, for example the mange-
; nose, copper, zinc, iron calcium, magnum and barium
salts, can be prepared from the sodium salts by reaction
with the corresponding metal chlorides in aqueous soul-
Sheehan kmmonium, sulfonium and phosphonium salts can be
obtained by reacting compounds of the formula I with
ammonium, suLfonium or phosphonium hydroxides, of
Lo
5 w Z 0050/3~2~0
necessary in aqueous solution.
he tricarbonyl compounds of the formula II are
novel. They can be prepared by conventional methods
tetrahedron Lotte 29 t1975~, 2491) from cyclohexane~
Dennis of the formula III, which may also occur in
the tautomeric forms IIIa and IIIb
I
-A A
R 0 Al OH Al
(III) (IIIa) (IIIb)
It us also possible to prepare the novel come
pounds of the formula II via the enlister inter-
mediates which are obtained, possibly as an isomer mixture, in the reaction of compounds of the formula
: III, and undergo rearrangement in the presence of an
imidazole or porn derivative (JP-A-63052/1979).
As is evident from the statements above, the in-
carbonyl compounds of the formula II are useful inter-
mediates in the preparation of herbicidal cyclohexenone
derivatives of the formula I.
The compounds of the formula XII can be obtained
by methods which are known from the literature, as is
evident from the scheme below:
Lo
- 6 - OOZE. 0050/37280
O f
I ( ) 2
base / \ p,vridine
C~$3
'\ 1
c~3-~
I ( CCX3 ) 2
C~-3QNa
A Cal Croci 5
SEIKO C~OC~3/C~3
0 '. '
COG Ox
1 ) Clue
,: 2) clue
~~~ .
A< .
.
O
~Z3~
- 7 - 0 Z. 0050/3728D
Aldehydes of the general formula A SHEA can be
obtained from the corresponding unsaturated aldehydes by
a conventional method; it may be necessary to protect
the alluded function.
The oxirane derivatives can be obtained in a
conventional manner by reacting the corresponding
unsaturated aldehydes or alluded derivatives with a
proxy compound such as hydrogen peroxide, tert.-butyl
hydroperoxide, per formic acid or m-chloroperben~o;~
acid, or with atmospheric oxygen.
The epox;de structure car, also be synthesized by
elimination of hydrogen halide from 1,2-halohydrins.
The thrown compounds can be prepared either by
reacting the corresponding epoxies with thiocyanates or
Thor, as described in, for example, J. Chum. Sock
1946, 1050, or by reacting the corresponding unsaturated
derivatives with sulfur transfer reagents, such as aureole
thiosulfenyl chlorides chemistry of Heterocyclic
Compounds, Al 42~ page 340). The transformation
methods described above can, if desired, be carried out
at any stage of synthesis.
The Examples which follow illustrate the pro-
parathion of the cyclohexenone derivatives of the formula
I. Parts by weight bear the same relation to parts by
Z5 volume as thaw of the kilogram to the liter.
The ~H-NMR spectra were recorded on solutions in
deuterochloroform as a solvent using tetramethylsilane
as an internal standard. The OH chemical shifts are
each stated in Pam The following abbreviations were
used to describe the signal structure:
s = singlet, d doublet, t - triplet, q = quartet and
m = multi pet strongest signal
EXAMPLE 1
3.5 parts by weight of bitterly 5-(3~4-epcxy-
cyclohexyl)-cyclohexane-1~3-dione, 1.5 parts by weight
of allylDxyammonium chloride and 1.2 parts by weight of
sodium bicarbonate on 50 parts by volume of methanol
8 - I 0050/37~0
were stirred for 16 hours at room temperature. The sol-
vent was distilled off under reduced pressure, the
residue was stirred with So parts by volume of water and
50 parts by volume of dichLoromethane, the organic phase
was separated off, the aqueous phase was extracted once
With 50 parts by volume of dichloromethane, the combined
organic phases were dried over sodium sulfate and the
solvent was distilled off under reduced pressure.
I Allyloxyiminobutyl)-5 t3,4-epoxycyclohexyl)-
3-hydroxycyclohex-2-en-1-one (active ingredient No. 1)
was obtained.
H-NMR spectrum: 0.95 (t), 2.9 (q), 5.3 em).
Example 2
3.5 parts by weight of Z-butyryl-5-(3,4-epoxy-
cyclohexyl) cyclohexane-1,3-dione and 0.8 part by weight
of ethoxyamine 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 dissolved in dichloromethane, the solution was
washed with 5% strength by weight hydrochloric arid and
water and tried over sodium sulfate, and the solvent was
distilled off under reduced pressure I Ethics-
iminobutyl)-5-~3,4-epoxycyclohexyl)-3-hydroxycycloohex~2-
en~1-one active ingredient No. 2) was obtained.
Z5 1H-NMR spectrum: 1.3 it), 3.2 my 4.1 I
EXAMPLE 3
9 parts by weight of 2-~1-propoxyiminobutyl)~
5-(cyclohex~3-enyl)-3-hydroxycyclohex-2-en-1-one were
dissolve in 100 parts by weight of dichloromethane~ and
So parts by weight of m-chloroperbenzoic acid about
80%) in 100 parts by volume of dichloromethane were
added drops at 5 - kiwi Tory one hour the course
of the reaction was checked by means of thin layer
chromatography using a precoated silica gel 60 TLC plate
and 1 : 1 cyclohexane/ethyl acetate as the mobile phase.
Further m-chLoroperbenzn;c acid was added drops until
I
- g - OOZE. ~050/37280
conversion was complete. Excess pursued was destroyed
by shaking with sodium thiosulfate solution. There-
after the mixture was extracted twice with semi-
saturated sodium bicarbonate solution and once with
water, the organic phase was dried over sodium sulfate
and the solvent was distilled off under reduced pros-
sure. I Propoxyiminobut yule (3,4-epoxycyclo-
- hexyl)-3-hydroxycyclohex-Z-en 1-one active ingredient
No 3) was obtained.
1H~NMR spectrum: 2.2 to), 3.1 (m), 4.0 (q).
The compounds below were obtained by methods
similar to those described on the Examples.
-10 - OOZE. 0050/37280
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The cyclohexenone derivatives of the formula I may be
applied for instance in the form of directly spray able
solutions, powders, suspensions (including high-percentage
aqueous, oily or other suspensions), dispersions, Emil-
05 sons, oil dispersions, pastes, dusts, broaacastingagents, 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, buy they must ensure as fine a distribution of the
active ingredient according to the invention as possible.
For the preparation of solutions, emulsions, pastes
and oil dispersions to be sprayed direct, mineral oil free-
lions of medium to high boiling point, such as kerosene or
diesel oil, further coal-tar oils and oils of vegetable
or animal origin, aliphatic, cyclic and aromatic hydra
carbons such as Bunsen, Tulane, zillion, paraffin, twitter-
hydronaphthalene, alkylated naphthalenes and their
derivatives such as methanol ethanol, propanol, buttonhole,
chloroform, carbon tetrachloride, cyclohexanol, cycle-
hexanone, chloroben7ene, isophorone, etc., and strongly polar solvents such as dimethylformamide, dim ethyl sulfa
oxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion
concentrates, pastes, oil dispersions or wettable powders
by adding water. To prepare emulsions, pastes and oil disk
pensions 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 waxer may be prepared
from active ingredient wetting agent, adherent, emulsify-
in 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, alkyd sulfates, and alkyd sulfonates, alkali
metal and alkaline earth metal salts of dibutylnaphthalene-
I
- 15 - OOZE. 0050/3728
sulfonic acid, laurel ether sulfate, fatty alcohol sup
fates, alkali metal and alkaline earth metal salts of
fatty acids, salts of sulfated hexadecanols, Hyatt-
decanols, and octadecanols, salts of sulfated fatty Alcoa
05 hot glycol ethers, condensation products of sulfonatednaphthalene and naphthalene derivatives with formaldehyde,
condensation products of naphthalene or naphthalenesul-
ionic acids with phenol and formaldehyde, polyoxyethylene
octylphenol ethers, ethoxylated isooctylphenol, elk-
lo oxylated octylphenol and ethoxylated nonylphenol, alkyd-
phenol polyglycol ethers, tributylphenyl polyglycol
ethers, alkylaryl polyether alcohols, isotridecyl alcohol,
fatty alcohol ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyd ethers, ethoxylated polyp
oxypropylene, laurel alcohol polyglycol ether acetal,sorbitol esters, lignin, sulfite waste liquors 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
granules, may be prepared by bonding the active inure-
dints to solid carriers. Examples of solid carriers are
mineral earths such as silicic acid, silica gels,
silicates, talc, kaolin, attapulgus clay, limestone, lime,
chalk, bole, loss, clay, dolomite, diatomaceous earth,
calcium sulfate, magnesium sulfate, magnesium oxide,
ground plastics, fertilizers such as ammonium sulfate,
ammonium phosphate, ammonium nitrate, and urea, and
vegetable products such as grain flours, bark meal, wood
meal, and nutshell meal, cellulosic powders etc.
The formulations contain from 0.1 to 95, and prefer-
ably 0.5 to 90, Jo by weight of active ingredient.
Examples of formulations are given below
Lo
- 16 - OOZE. 0050~37280
X. Jo parts by weight of compound no. 1 is mixed
with 10 parts by weight of N-methyl~alpha-pyrrolidone. A
mixture is obtained which is suitable for application in
the form of very fine drops.
05 II. 20 parts by weight of compound no. 2 is dls-
solved in a mixture consisting of 80 parts by weight of
zillion, 10 parts by weight of the adduce of 8 to 10 moles
of ethylene oxide and 1 mole of oleic acid-N-monoethanol
aside, 5 parts by weight of the calcium salt of dodecyl-
benzenesulfonic acid, and 5 parts by weight of the adduce
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 dispel-
soon is obtained containing 0.02~ by weight of the active
ingredient.
III. I parts by weight of compound no. 1 is disk
solved in a mixture consisting of 40 parts by weight of
cyclohexanone, 30 parts by weight of isobutanol, 20 parts
by weight of the adduce of 7 moles of ethylene oxide and
1 mole of isooctylphenol, and 10 parts by weight of the
adduce 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. 4 is disk
solved in a mixture consisting of 25 parts by weight of
cyclohexanol, 65 parts by weight of a mineral oil fraction
having a boiling point between 210 and 280C! and
10 parts by weight of the adduce 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.
V. 20 parts by weight of compound no. 6 is well
mixed with 3 parts by weight of the sodium salt of dliso-
- 17 I ~050/37280
butylnaphthalene-alpha-sulfonic acid, 17 parts by weight
of the sodium salt of a lignin-sulfonic acid obtained from
a sulfite waste liquor, and 60 parts by weight of powdered
silica gel, and triturated in a hammer mill. By uniformly
05 distributing the mixture in 20,000 parts by weight of
water, a spray liquor is obtained containing 0.1~; by
weight of the active ingredient.
VI. 3 parts by weight of compound no. 13 is
intimately mixed with 97 parts by weight of particulate
kaolin. A dust is obtained containing I by weight of the
active ingredient.
VII. 30 parts by weight of compound no. 11 is
intimately mixed with a mixture consisting of 92 parts by
weight of powdered silica gel and 8 parts by weight of
paraffin oil which has been sprayed onto the surface of
this silica gel. A formulation of the active ingredient is
obtained having good adherence.
VIII. 20 parts of compound no. 1 is intimately mixed
with 2 parts of the calcium salt of dodecylbenzenesulfonic
acid, 8 parts of a fatty alcohol polyglycol ether, 2 parts
of the sodium salt of a phenolsulfonic acid-urea form-
alluded condensate and 68 parts of a paraffinic mineral
oil. A stable oily dispersion is obtained.
The active ingredients, or agents containing them,
may be applied pro- or postemergnece. If certain crop
plants tolerate the active ingredients less well,
application techniques may be used in which the herbicidal
agents are sprayed from suitable 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).
Thy amount of active ingredient applied depends on
the time of the year, the plants to be combated and their
growth stage, and varies from 0.025 to 3 kg/ha, but is
preferably from 0.05 to 0.5 kg/ha.
~L23~
- 18 - OOZE 0050/37280
The action of the cyelohexenone derivatives of the
formula I on plant growth is demonstrated in greenhouse
experiments.
The vessels employed were plastic flowerpots having a
05 volume of 300 cm3, and wisher filled with a sandy loam
containing about 3.0~j humus. The seeds of the test plants
were sown shallow, and separately, according to species.
For the reemergence treatment, the active ingredients
were applied to the surface of the soil immediately after
the seeds had been sown. The compounds were emulsified or
suspended in water as vehicle, and sprayed through finely
distributing nozzles. The application rate was 3.0 kg of
active ingredient per Hector. 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 ensure uniform germination of the plants,
insofar as this was not impaired by the active inure-
dints.
For the post emergence treatment, the plants were
first grown in the vessels to a height of from 3 to 15 cm,
depending on growth form, before being treated. The soy-
bean 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 been grown from seedlings and were transplanted to the
pots a few days before treatment. The application rates
for post emergence treatment were 0.06 to 0.125 kg of
active ingredient per Hector. No covers were placed on
the vessels in this method.
The pots were set up in the greenhouse - species from
warmer areas at from 20 to 35C, and species from moderate
climates at 10 to 25~C. 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 0 to 100, 0 denoting no
I
- 19 - OOZE 0050/37280
damage or normal emergence, and 100 denoting non emergence
or complete destruction of at least the visible plant parts.
The plants used in the experiments were Alopecurus
myosuxoides, Arena fish, Arena saliva, Digit aria swung
05 nails, Echinochloa crus-galli, Gleason max., Lolium multi-
forum, Satyr italic, Synapse alga, Sorghum halepense,
Sorghum buckler, and Zeta may.
The compounds used for comparison purposes were
I allyloxyamino-n-butyl)~5-(cyclohex-l~en-4 yule-
-hydroxycyclohex-2-en-1-one (A) and I ethoximino-n-
-butyl)-5-(cyclohex-1-en-4-yl)-3-hydroxycyclohex-~~-en-1-one
(B) disclosed in German DE-A-3 032 973, and ethics-
amino-nbutyl)-5-(cyclooct-1-en-5-yl)-3-hydroxycyclohex-2--
en-l-one (C) disclosed in German DE-A-3 219 490, and
herbicidal agents containing these compounds.
On preemer~ence application, compounds nos. 4, 6, 11
and 13, for instance, had a herbicidal action on plants
from the grasses family, whereas Synapse alga, as a
dicotyledonous representative, remained completely
undamaged.
or example compounds nos. 4 and 6, applied post-
emergence at a rate of 0.125 kg/ha, had a strong
herbicidal action on a broad spectrum of grassy weeds;
soybeans, as dicotyledonous crop plants, suffered no
damage whatsoever.
Unwanted grass species were combated well by, for
example, compounds nos. 26, 28, 52, 53, 55 and 61, whereas
the broad leaved crop plant alfalfa remained completely
undamaged.
Compound no. 8, for example, was suitable at low
application rates for controlling undesirable grass
species, and was tolerated by wheat.
Compounds nos. 1 and 2 selected by way of example
control problem grasses much better than prior art
comparative agents A and B, and are fully tolerated by
soybeans.
I
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Compared with prior art agent C, the degree of
herbicidal action of, for instance, compound no. 50 is
significantly higher, without compatibility for alfalfa
being influenced.
05 In view of the spectrum of weeds which can be come
batted, the tolerance of the active ingredients according
to the invention by crop plants, the desired influence on
the growth of crop plants, and in view of the numerous
application methods possible, the compounds according to
may be used in a large number of crop plants.
The following may be mentioned by way of example:
Botanical name Common name
Allele cope onions
15 Bananas comosus pineapples
Arachis hypogaea peanuts (groundnuts)
Asparagus officinalis asparagus
Arena saliva oats
Beta vulgarism sup. altissima sugar beets
20 Beta vulgarism 5pp. nape fodder beets
Beta vulgarism sup. esculenta table beets, red beets
Brusque naps var. naps rhapsody
Brusque naps var. napobrassica suedes
Brusque naps var. nape turnips
25 Brusque nape var. silvestris
Camellia sinensis tea plants
Carthamus tinctures safflower
Carve illinoinensis pecan trees
Citrus lion lemons
30 Citrus maxima grapefruits
Citrus reticulate mandarins
Citrus sinensis orange trees
Coffee Arabic (Coffee conifer,
Coffee Liberia) coffee plants
35 Cucumis memo melons
Cucumis sativus cucumbers
~23~
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Botanical name Common name
Sundown dactyl on Bermuda grass in turf
and lawns
05 Caucus karat carrots
flats guineensis oil palms
Fragaria vesca strawberries-
Gleason Max soybeans
Gossypium hirsutum
10 ~Gossypium arboretum cotton
Gossypium herbaceum
Gossypium vitifolium)
Helianthus annuls sunflowers
Helianthus tuberosus Jerusalem artichoke
15 Hove brasiliensis rubber plants
Hordeum vulgar barley
Cumulus lapels hops
Ipomoea batatas sweet potatoes
Juglans Regina walnut trees
20 Lactic saliva lettuce
yens culinaris lentils
Linus usitatissimum flax
Lycopersicon lycopersicum tomatoes
Mauls sup. apple trees
25 Monet esculenta cohesive
Medic ago saliva alfalfa (Lucerne)
Month paperweight peppermint
Muse sup. banana plants
Nicothiana tabacum tobacco
30 ON. rustic)
: Olga europaea olive trees
Ours saliva rice
Panicum miliaceum millet
Fossils lunatus lima beans
35 Fossils mango mungbeans
Fossils vulgarism snap beans, green beans,
dry beans
123~
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Botanical name Common name
Pennisetum glaucoma pearl millet
Petroselinum crispum parsley
05 sup- tuberosum
Pica abides Norway spruce
Abides alga fir trees
Pious sup. pine trees
Possum sativum English peas
10 Prunes avium cherry trees
Prunes domestic plum trees
Prunes dualizes almond trees
Prunes Persia peach trees
Pyres communist pear trees
15 Robes Sylvester redcurrants
Robes uva-crispa gooseberries
Rosins communist castor-oil plants
Saccharum officinarum sugar cane
Scale cereal rye
on Sesamum indicum sesame
Selenium tuberosum Irish potatoes
Sorghum buckler (s. vulgar) sorghum
Sorghum dochna forgo
Spanish oilers spinach
Theobroma cacao cacao plants
Trifolium pretense red clover
Triticum aestivum wheat
Vaccinium corymbosum blueberries
Vaccinium vitis-idaea cranberries
30 Viola phoebe tick beans
Vegan sinensis (V. unguiculata) cow peas
Votes veneerer grapes
Zeta may Indian corn, sweet
corn maize
I (post-directed)
To increase the spectrum of action and to achieve
synergistic effects, the novel substituted cyclohexenone
- 23 - OOZE 0050/37280
derivatives may be mixed and applied together with
numerous representatives of other herbicidal or growth-
-regulating active ingredient groups. Examples of suitable
mixture components are Dennis, 4H-3,1-benzoxazine
OX derivatives r benzothiadiazinones, 2,6-dinitroanilines,
N-phenylcarbamates, thiolcarbamates, halocarboxylic acids,
treasons, asides, ureas/ diphenyl ethers, triazinones,
uracils, benzofuran derivatives, quinolinecarboxylic acid
derivatives, etc.
It may also be useful to apply the cyclohe~enone
derivatives of the formula I, either alone or in comb-
nation with other herbicides in admixture with other crop
protection agents, e.g., agents for combating pests or
phytopathogenic fungi 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.
; ' '
