Herbicidal compositions comprising pyroxasulfone
The present invention relates to herbicidally active compositions, which comprise 3-[5-
(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-
5,5-dimethyl-1,2-oxazole [common name pyroxasulfone] and at least one herbicide B.
Background of the invention
In crop protection, it is desirable in principle to increase the specificity and the reliability
of the action of active compounds. In particular, it is desirable for the crop protection
product to control the harmful plants effectively and, at the same time, to be tolerated
by the useful plants in question.
Pyroxasulfone has been described in EP-A 1364946 and US 2005/0256004.
Although pyroxasulfone is a highly effective pre-emergence herbicide, its activity at low
application rates is not always satisfactory. Moreover, pyroxasulfone is known to have
only poor post-emergence activity (Y. Yamaji et al., "Application timing and field per-
formance of KIH-485", Conference Abstract l-1-ii-12B of 11. IUPAC International Con-
gress of Pesticide Chemistry, 2006 Kobe, Japan). Apart from that, its compatibility with
certain dicotyledonous crop plants such as cotton, sunflower, soybean, brassica crops
such as canola and oilseed rape and some graminaceous plants such as rice, wheat,
rye and barley is not always satisfactory, i.e. in addition to the harmful plants, the crop
plants are also damaged to an extent which is not acceptable. Though it is in principle
possible to spare crop plants by lowering the application rates, the extent of the control
of harmful plants is naturally also reduced.
It is known that combined application of certain different herbicides with specific action
might result in an enhanced activity of a herbicide component in comparison with a
simple additive action. Such an enhanced activity is also termed a synergism or syner-
gistic activity. As a consequence, it is possible to reduce the application rates of herbi-
cidally active compounds required for controlling the harmful plants.
WO 2005/104848 describes compositions containing a herbicidal 3-sulfonylisoxazoline
compound such as pyroxasulfone and a herbicide-antagonistically active amount of a
safener. Similar compositions are known from WO 2007/006509.
US 2005/256004, for example, discloses that in a pre-emergence treatment, joint appli-
cation of certain herbicidal 3-sulfonylisoxazoline compounds such as pyroxasulfone
with atrazine or cyanazine results in an increased overall herbicide action against cer-

tain monocotyledonous and dicotyledonous annual broad leaf weeds (lambsquarter,
green foxtail, velvetleaf) in comparison with a simple expected additive action.
WO 2006/097322 discloses a herbicidal composition comprising pyroxasulfone and a
second herbicide selected from tembotrione, topramezone and 4-hydroxy-3-[[2-[(2-
methoxyethoxy)methyl]-6-(trifluoromethyl-3-pyridinyl]carbonyl]bicyclo[3.2.1]oct-3-ene-2-
one.
WO 2006/097509 discloses a herbicidal composition comprising a herbicidal 3-
sulfonylisoxazoline compound such as pyroxasulfone and a phenyluracil compound.
Unfortunately, it is usually not possible to predict synergistic activity for combinations of
known herbicides, even if the compounds show a close structural similarity to known
synergistic combinations.
Summary of the invention
It is an object of the present invention to provide herbicidal compositions, which show
enhanced herbicide action in comparison with the herbicide action of pyroxasulfone
against undesirable harmful plants, in particular against Alopecurus myosuroides,
Avena fatua, Bromus spec, Echinocloa spec. Lolium spec, Phalaris spec, Setaria
spec, Digitaria spec, Brachiaria spec, Amaranthus spec, Chenopodium spec, Abuti-
lon theophrasti, Galium aparine, Veronica spec, or Solanum spec, and/or to improve
their compatibility with crop plants, in particular improved compatibility with wheat, bar-
ley, rye, rice, soybean, sunflower, brassica crops and/or cotton. The composition
should also have a good herbicidal activity in post-emergence applications. The com-
positions should also show an accelerated action on harmful plants, i.e. they should
effect damaging of the harmful plants more quickly in comparison with application of
the individual herbicides.
We have found that this object is achieved, surprisingly, by herbicidally active composi-
tions comprising
a) pyroxasulfone, i.e. 3-[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-
ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole (hereinafter also referred
to as herbicide A);
and
b) at least one herbicide B which is an inhibitor of microtubule assembly.

The invention relates in particular to compositions in the form of herbicidally active
compositions as defined above.
The invention also relates to the use of a composition as defined herein for controlling
undesirable vegetation. When using the compositions of the invention for this purpose
the herbicide A and the at least one herbicide B can be applied simultaneously or in
succession, where undesirable vegetation may occur.
The invention furthermore relates to the use of a composition as defined herein for con-
trolling undesirable vegetation in crops. When using the compositions of the invention
for this purpose the herbicide A and the at least one herbicide B can be applied simul-
taneously or in succession in crops, where undesirable vegetation may occur.
The invention furthermore relates to the use of a composition as defined herein for con-
trolling undesirable vegetation in crops which, by genetic engineering or by breeding,
are resistant or tolerant to one or more herbicides and/or pathogens such as plant-
pathogenous fungi, and/or to attack by insects; preferably resistant or tolerant to one or
more herbicides that act as inhibitors of microtubule assembly.
The invention furthermore relates to a method for controlling undesirable vegetation,
which comprises applying an herbicidal composition according to the present invention
to the undesirable plants. Application can be done before, during and/or after, prefera-
bly during and/or after, the emergence of the undesirable plants. The herbicide A and
the at least one herbicide B can be applied simultaneously or in succession.
The invention in particular relates to a method for controlling undesirable vegetation in
crops, which comprises applying an herbicidal composition according to the present
invention in crops where undesirable vegetation occurs or might occur.
The invention furthermore relates to a method for controlling undesirable vegetation,
which comprises allowing a composition according to the present invention to act on
plants, their habitat or on seed.
In the uses and methods of the present invention it is immaterial whether the herbicide
A and the at least one herbicide B are formulated and applied jointly or separately, and,
in the case of separate application, in which order the application takes place. It is only
necessary, that the herbicide A and the at least one herbicide B are applied in a time
frame, which allows simultaneous action of the active ingredients on the plants.

The invention also relates to a herbicide formulation, which comprises a herbicidaly
active composition as defined herein and at least one carrier material, including liquid
and/or solid carrier materials.
Detailed description of the invention
Surprisingly, the compositions according to the invention have better herbicidal activity
against harmful plants than would have been expected by the herbicidal activity of the
individual compounds. In other words, the joint action of pyroxasulfone and the at least
one herbicide B results in an enhanced activity against harmful plants in the sense of a
synergy effect (synergism). For this reason, the compositions can, based on the indi-
vidual components, be used at lower application rates to achieve a herbicidal effect
comparable to the individual components. Moreover, the compositions of the present
invention provide good post-emergence herbicidal activity, i.e. the compositions are
particularly useful for combating/controlling harmful plants after their emergence. Apart
form that, the compositions of the present invention show good crop compatibility, i.e.
their use in crops leads to a reduced damage of the crop plants and/or does not result
in increased damage of the crop plants.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
The compositions of the invention comprise pyroxasulfone as a first component a).
As a second component b), the compositions of the invention comprise at least one
herbicide B which is an inhibitor of microtubule assembly (MTA inhibitor). MTA inhibi-
tors are compounds which have a mode of action comprising the inhibition of the micro-
tubule assembly in plants and which belong to the group K1 of the HRAC classification
system (see HRAC, Classification of Herbicides According to Mode of Action,
http://www.plantprotection.org/hrac/MOA.html).
MTA inhibitors include e.g. dinitroaniline herbicides, such as benfluralin, butralin, dini-
tramine, ethalfluralin, oryzalin, pendimethalin, and trifluralin, phosphoroamidate herbi-
cides, such as amiprophos-methyl and butamiphos, pyridine herbicides, such as di-
thiopyr and thiazopyr, benzamide herbicides, such as propyzamide and tebutam, and
benzoic acid herbicides, such as chlorthal. The term "MTA inhibitor" is meant herein to
also include the respective salts, isomers and esters of the above mentioned com-
pounds. Suitable salts are e.g. salts of alkaline or earth alkaline metals or ammonium
or organoammonium salts, for instance, sodium, pottasium, ammonium, isopropyl am-

monium etc. Suitable isomers are e.g. stereo isomers such as the enantiomers. Suit-
able esters are e.g. C1-C8-(branched or non-branched) alkyl esters, such as me-
thylesters, ethylesters, iso propyl esters.
Preferred MTA inhibitors according to the present invention are selected from the group
consisting of dinitroaniline herbicides, in particular from the group consisting of
benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, isopropalin, methalpropalin,
nitralin, oryzalin, pendimethalin, prodiamine, profluralin and trifluralin, especially
prodiamine, oryzalin, pendimethalin and trifluralin and pyridine herbicides, in particular
from the group consisting of dithiopyr and thiazopyr.
In the compositions of the present invention the relative weight ratio of pyroxasulfone to
herbicide B is preferably in the range from 1:250 to 250:1 and more preferably from
100:1 to 1:100. Accordingly, in the methods and uses of the invention, pyroxasulfone
and the at least one herbicide B are applied within these weight ratios.
The compositions of the invention may also comprise, as a component c), one or more
safeners. Safeners, also termed as herbicide safeners, are organic compounds which
in some cases lead to better crop plant compatibility when applied jointly with specifi-
cally acting herbicides. Some safeners are themselves herbicidally active. In these
cases, the safeners act as antidote or antagonist in the crop plants and thus reduce or
even prevent damage to the crop plants. However, in the compositions of the present
invention, safeners are generally not required. Therefore, a preferred embodiment of
the invention relates to compositions which contain no safener or virtually no safener
(i.e. less than 1 % by weight, based on the total amount of herbicide A and herbicide
B).
Suitable safeners, which can be used in the compositions according to the present in-
vention, are known in the art, e.g. from
The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/);
Farm Chemicals Handbook 2000 Vol. 86, Meister Publishing Company, 2000;
B. Hock, C. Fedtke, R. R. Schmidt, Herbizide, Georg Thieme Verlag, Stuttgart 1995;
W. H. Ahrens, Herbicide Handbook, 7th Edition, Weed Science Society of America,
1994; and
K. K. Hatzios, Herbicide Handbook, Supplement to 7th Edition, Weed Science Society
of America, 1998.
Safeners include e.g. benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid,
dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole,
isoxadifen, mefenpyr, mephenate, naphthalic anhydride, 2,2,5-trimethyl-3-

(dichloracetyl)-l ,3-oxazolidine, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane and
oxabetrinil, as well as thereof agriculturally acceptable salts and, provided they have a
carboxyl group, their agriculturally acceptable derivatives. 2,2,5-Trimethyl-3-
(dichloroacetyl)-l ,3-oxazolidine [CAS No. 52836-31-4] is also known under the name
R-29148.4-(Dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane [CAS No. 71526-07-03] is
also known under the names AD-67 and MON 4660.
As a safener, the compositions according to the invention particularly preferably com-
prise at least one of the compounds selected from the group of benoxacor, cloquinto-
cet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, fluxofenim, furilazole,
isoxadifen, mefenpyr, naphthalic anhydride, 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-
oxazolidine, and 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane and oxabetrinil; and
the agriculturally acceptable salt thereof and, in the case of compounds having a
COOH group, an agriculturally acceptable derivative as defined below.
A preferred embodiment of the invention relates to compositions which contain no
safener or virtually no safener (i.e. less than 1 % by weight, based on the total amount
of herbicide A and the at least one herbicide B is applied).
The compositions of the invention may also comprise, as a component d), one or more
herbicides D which are different from the herbicides A and B. Such further herbicides D
may broaden the activity spectrum of the inventive compositions. However, further
herbicides D are generally not required. Therefore, a preferred embodiment of the in-
vention relates to compositions which contain no further herbicide D or virtually no fur-
ther herbicide D (i.e. less than 1 % by weight, based on the total amount of herbicide A
and herbicide B).
In particular, the compositions of the present invention consist of the herbicide A and
the at least one herbicide B, i.e. they neither contain a safener nor a further herbicide
D.
In another preferred embodiment of the invention, the composition additionally contain
a further herbicide D which is selected from the group consisting of dimethenamid, di-
methenamid-P, flufenacet, metribuzin, flupyrsulfuron, picolinafen and prosulfocarb.
If the compounds of herbicide compounds mentioned as herbicides B, herbicides D
and safeners (see below) have functional groups, which can be ionized, they can also
be used in the form of their agriculturally acceptable salts. In general, the salts of those
cations are suitable whose cations have no adverse effect on the action of the active
compounds ("agricultural acceptable").

In general, the salts of those cations are suitable whose cations have no adverse effect
on the action of the active compounds ("agricultural acceptable"). Preferred cations are
the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline
earth metals, preferably of calcium and magnesium, and of the transition metals, pref-
erably of manganese, copper, zinc and iron, furthermore ammonium and substituted
ammonium (hereinafter also termed as organoammonium) in which one to four hydro-
gen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl,
hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl or benzyl, preferably ammonium, methylam-
monium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethyl-
ammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-
hydroxyethylammonium, 2-(2-hydroxyethoxy)eth-1-ylammonium (diglycolamine salts),
di(2-hydroxyeth-1-yl)ammonium (diolamine salts), tris((2-hydroxyeth-1-yl)ammonium
(trolamine salts), tris(3-propanol)amonium, benzyltrimethylammonium, benzyltriethyl-
ammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-
alkyl)sulfonium such as trimethylsulfonium, and sulfoxonium ions, preferably tri(C1-C4-
alkyl)sulfoxonium.
In the compositions according to the invention, the compounds that carry a carboxyl
group can also be employed in the form of agriculturally acceptable derivatives, for
example as amides such as mono- or di-C1-C6-alkylamides or arylamides, as esters,
for example as allyl esters, propargyl esters, C1-C10-alkyl esters or alkoxyalkyl esters,
and also as thioesters, for example as C1-C10-alkyl thioesters. Preferred mono- and di-
C1-C6-alkylamides are the methyl- and the dimethylamides. Preferred arylamides are,
for example, the anilidines and the 2-chloroanilides. Preferred alkyl esters are, for ex-
ample, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl)
or isooctyl (2-ethylhexyl) esters. Preferred C1-C4-alkoxy-C1-C4-alkyl esters are the
straight-chain or branched C1-C4-alkoxyethyl esters, for example the methoxyethyl,
ethoxyethyl or butoxyethyl esters. An example of the straight-chain or branched C1-C10-
alkyl thioesters is the ethyl thioester. Preferred derivatives are the esters.
The compositions of the present invention are suitable for controlling a large number of
harmful plants, including monocotyledonous weeds, in particular annual weeds such as
gramineous weeds (grasses) including Echinochloa species such as barnyardgrass
(Echinochloa crusgalli var. crus-galli), Digitaria species such as crabgrass (Digitaria
sanguinalis), Setaria species such as green foxtail (Setaria viridis) and giant foxtail (Se-
taria faberii), Sorghum species such as johnsongrass (Sorghum halepense Pers.),
Avena species such as wild oats (Avena fatua), Cenchrus species such as Cenchrus
echinatus, Bromus species, Lolium species, Phalaris species, Eriochloa species, Pani-
cum species, Brachiaria species, annual bluegrass (Poa annua), blackgrass (Alopecu-

rus myosuroides), Aegilops cylindrica, Agropyron repens, Apera spica-venti, Eleusine
indica, Cynodon dactylon and the like.
The compositions of the present invention are also suitable for controlling a large num-
ber of dicotyledonous weeds, in particular broad leaf weeds including Polygonum spe-
cies such as wild buckwheat (Polygonum convolvolus), Amaranthus species such as
pigweed (Amaranthus retroflexus), Chenopodium species such as common lambsquar-
ters (Chenopodium album L), Sida species such as prickly sida (Sida spinosa L), Am-
brosia species such as common ragweed (Ambrosia artemisiifolia), Acanthospermum
species, Anthemis species, Atriplex species, Cirsium species, Convolvulus species,
Conyza species, Cassia species, Commelina species, Datura species, Euphorbia spe-
cies, Geranium species, Galinsoga species, morningglory (Ipomoea species), Lamium
species, Malva species, Matricaria species, Sysimbrium species, Solanum species,
Xanthium species, Veronica species, Viola species, common chickweed (Stellaria me-
dia), velvetleaf (Abutilon theophrasti), Hemp sesbania (Sesbania exaltata Cory), Anoda
cristata, Bidens pilosa, Brassica kaber, Capsella bursa-pastoris, Centaurea cyanus,
Galeopsis tetrahit, Galium aparine, Helianthus annuus, Desmodium tortuosum, Kochia
scoparia, Mercurialis annua, Myosotis arvensis, Papaver rhoeas, Raphanus raphanis-
trum, Salsola kali, Sinapis arvensis, Sonchus arvensis, Thlaspi arvense, Tagetes
minuta, Richardia brasiliensis, and the like.
The compositions of the present invention are also suitable for controlling a large num-
ber of annual and perennial sedge weeds including cyperus species such as purple
nutsedge (Cyperus rotundus L), yellow nutsedge (Cyperus esculentus L), hime-kugu
(Cyperus brevifolius H.), sedge weed (Cyperus microiria Steud), rice flatsedge (Cype-
rus iria L), and the like.
The compositions according to the present invention are suitable for combat-
ing/controlling common harmful plants in useful plants (i.e. in crops). The compositions
of the present invention are generally suitable for combating/controlling undesired
vegetation in
Grain crops, including e.g.
cereals (small grain cereals) such as wheat (Triticum aestivum) and wheat
like crops such as durum (T. durum), einkorn (T. monococcum), emmer (7".
dicoccon) and spelt (T. spelta), rye (Secale cereale), triticale (Tritiosecale),
barley (Hordeum vulgare);
maize (com; Zea mays);
sorghum (e.g. Sorghum bicolour);
rice (Oryza spp. such as Oryza sativa and Oryza glaberrima); and
sugar cane;

Legumes (Fabaceae), including e.g. soybeans (Glycine max.), peanuts (Arachis
hypogaea and pulse crops such as peas including Pisum sativum, pigeon pea
and cowpea, beans including broad beans (Vicia faba), Vigna spp., and Phaseo-
lus spp. and lentils (lens culinaris var.);
brassicaceae, including e.g. canola (Brassica napus), oilseed rape (Brassica
napus), cabbage (B. oleracea var.), mustard such as B. juncea, B. campestris, B.
narinosa, B. nigra and B. tournefortir, and turnip (Brassica rapa var.);
other broadleaf crops including e.g. sunflower, cotton, flax, linseed, sugarbeet,
potato and tomato;
TNV-crops (TNV: trees, nuts and vine) including e.g. grapes, citrus, pomefruit,
e.g. apple and pear, coffee, pistachio and oilpalm, stonefruit, e.g. peach, almond,
walnut, olive, cherry, plum and apricot;
turf, pasture and rangeland;
onion and garlic;
bulb ornamentals such as tulips and narcissus;
conifers and deciduous trees such as pinus, fir, oak, maple, dogwood, haw-
thome, crabapple, and rhamnus (buckthorn); and
garden ornamentals such as petunia, marigold, roses and snapdragon.
The compositions of the present invention are in particular suitable for combat-
ing/controlling undesired vegetation in wheat, barley, rye, triticale, durum, rice, corn,
sugarcane, sorghum, soybean, pulse crops such as pea, bean and lentils, peanut, sun-
flower, sugarbeet, potato, cotton, brassica crops, such as oilseed rape, canola, mus-
tard, cabbage and turnip, turf, grapes, pomefruit, such as apple and pear, stonefruit,
such as peach, almond, walnut, olive, cherry, plum and apricot, citrus, coffee, pistachio,
garden ornamentals, such as roses, petunia, marigold, snap dragon, bulb ornamentals
such as tulips and narcissus, conifers and deciduous trees such as pinus, fir, oak, ma-
ple, dogwood, hawthorne, crabapple and rhamnus.
The compositions of the present invention are most suitable for combating/controlling
undesired vegetation in wheat, barley, rye, triticale, durum, rice, corn, sugarcane, sor-
ghum, soybean, pulse crops such as pea, bean and lentils, peanut, sunflower,
sugarbeet, potato, cotton, brassica crops, such as oilseed rape, canola, mustard, cab-
bage and turnip, turf, grapes, stonefruit, such as peach, almond, walnut, olive, cherry,
plum and apricot, citrus and pistachio.
If not stated otherwise, the compositions of the invention are suitable for application in
any variety of the aforementioned crop plants.

The compositions of the invention are particularly suitable for application in wheat, bar-
ley, rye, triticale, durum, rice, corn, sorghum, sugarcane, soybean, pulse crops, bras-
sica crops, turf, stonefruit, citrus and grapes.
The compositions according to the invention can also be used in crop plants which are
resistant or tolerant to one or more herbicides owing to genetic engineering or breed-
ing, which are resistant or tolerant to one or more pathogens such as fungi owing to
genetic engineering or breeding, or which are resistant or tolerant to attack by insects
owing to genetic engineering or breeding. Suitable are for example crop plants, pref-
erably corn, wheat, sunflower, rice, canola, oilseed rape, soybeans or lentils which are
resistant or tolerant to herbicidal MTA inhibitors, such as, for example, prodiamine,
oryzalin, pendimethalin, trifluralin, dithiopyr, or thiazopyr or crop plants which, owing to
introduction of the gene for Bt toxin by genetic modification, are resistant to attack by
certain insects.
The compositions of the present invention can be applied in conventional manner by
using techniques a skilled person is familiar with. Suitable techniques include spraying,
atomizing, dusting, spreading or watering. The type of application depends on the in-
tended purpose in a well known manner; in any case, the techniques should ensure the
finest possible distribution of the active ingredients according to the invention.
The compositions can be applied pre- or post-emergence, i.e. before, during and/or
after emergence of the undesirable plants. When the compositions are used in crops,
they can be applied after seeding and before or after the emergence of the crop plants.
The compositions invention can, however, also be applied prior to seeding of the crop
plants.
It is a particular benefit of the compositions according to the invention that they have a
very good post-emergence herbicide activity, i.e. they show a good herbicidal activity
against emerged undesirable plants. Thus, in a preferred embodiment of invention, the
compositions are applied post-emergence, i.e. during and/or after, the emergence of
the undesirable plants. It is particularly advantageous to apply the mixtures according
to the invention post emergent when the undesirable plant starts with leaf development
up to flowering. Since the composition show good crop tolerance, even when the crop
has already emerged, they can be applied after seeding of the crop plants and in par-
ticular during or after the emergence of the crop plants.
In any case herbicide A and the at least one herbicide B and the optional further ac-
tives (safener C and herbicide D) can be applied simultaneously or in succession.

The compositions are applied to the plants mainly by spraying, in particular foliar spray-
ing. Application can be carried out by customary spraying techniques using, for exam-
ple, water as carrier and spray liquor rates of from about 10 to 2000 l/ha or 50 to 1000
l/ha (for example from 100 to 500 l/ha). Application of the herbicidal compositions by
the low-volume and the ultra-low-volume method is possible, as is their application in
the form of microgranules.
If the active ingredients are less well tolerated by certain crop plants, application tech-
niques may be used in which the herbicidal compositions are sprayed, with the aid of
the spray apparatus, in such a way that they come into as little contact, if any, with the
leaves of the sensitive crop plants while reaching the leaves of undesirable plants,
which grow underneath, or the bare soil (post-directed, lay-by).
In the case of a post-emergence treatment of the plants, the herbicidal mixtures or
compositions according to the invention are preferably applied by foliar application.
Application may be effected, for example, by usual spraying techniques with water as
the carrier, using amounts of spray mixture of approx. 50 to 1000 l/ha.
The required application rate of the composition of the pure active compounds, i.e. of
pyroxasulfone, herbicide B and optionally safener or herbicide D depends on the den-
sity of the undesired vegetation, on the development stage of the plants, on the climatic
conditions of the location where the composition is used and on the application
method. In general, the application rate of the composition (total amount of pyroxasul-
fone, herbicide B and optional further actives) is from 15 to 6000 g/ha or from 15 to
5000 g/ha, preferably from 20 to 2500 g/ha of active substance.
The required application rates of pyroxasulfone are generally in the range from 1 g/ha
to 500 g/ha and preferably in the range from 5 g/ha to 400 g/ha or from 10 g/ha to 300
g/ha of active substance.
The required application rates of the herbicide B (total amount of herbicide B) are gen-
erally in the range from 10 g/ha to 5000 g/ha and preferably in the range from 50 g/ha
to 4000 g/ha or from 100 g/ha to 2500 g/ha of active substance.
The required application rates of the safener, if applied, are generally in the range from
1 g/ha to 5000 g/ha and preferably in the range from 2 g/ha to 5000 g/ha or from 5 g/ha
to 5000 g/ha of active substance. Preferably no safener or virtually no safener is ap-
plied and thus the application rates are below 5 g/ha, in particular below 2 g/ha or be-
low 1 g/ha.

The required application rates of the further herbicide D, if applied, depends from the
nature of the herbicide D and may generally be in the range from 0.1 g/ha to 5000 g/ha
and preferably in the range from 1 g/ha to 5000 g/ha or from 2 g/ha to 5000 g/ha of
active substance.
The weight ratio of pyroxasulfone and herbicide D, if applied, depends from the nature
of the herbicide D and may generally be in the range 500:1 to 1:500, in particular from
250:1 to 1:250.
In case of flupyrsulfuron, the application rate is generally in the range of 0.1 to 200
g/ha, preferably from 1 to 150 g/ha, in particular from 2 to 100 g/ha of active substance.
The weight ratio of pyroxasulfone and flupyrsulfuron, if applied, may generally be in the
range 500:1 to 1:500, in particular from 250:1 to 1:250.
In case of dimethenamid and dimethenamid P, the application rate is generally in the
range of 1 to 5000 g/ha, preferably from 5 to 4000 g/ha, in particular from 10 to 3000
g/ha of active substance. The weight ratio of pyroxasulfone and dimethenamid or di-
methenamid-P, if applied, may generally be in the range 250:1 to 1:250, in particular
from 100:1 to 1:100.
In case of flufenacet, the application rate is generally in the range of 1 to 1500 g/ha,
preferably from 5 to 1000 g/ha, in particular from 10 to 750 g/ha of active substance.
The weight ratio of pyroxasulfone and flufenacet, if applied, may generally be in the
range 100:1 to 1:100, in particular from 50:1 to 1:50.
In case of picolinafen, the application rate is generally in the range of 1 to 500 g/ha,
preferably from 5 to 400 g/ha, in particular from 10 to 250 g/ha of active substance. The
weight ratio of pyroxasulfone and picolinafen, if applied, may generally be in the range
100:1 to 1:100, in particular from 50:1 to 1:50.
In case of prosulfocarb, the application rate is generally in the range of 1 to 5000 g/ha,
preferably from 5 to 4500 g/ha, in particular from 10 to 4000 g/ha of active substance.
The weight ratio of pyroxasulfone and prosulfocarb, if applied, may generally be in the
range 500:1 to 1:500, in particular from 250:1 to 1:250.
According to a first embodiment of the invention, the component b) comprises at least
one dinitroaniline herbicide. Dinitroaniline herbicides are known e.g. from US
3,257,190: US 3,321,292; US 3,367,949; C.D.S. Tomlin, "The Pesticide Manual", 13th
Edition, BCPC (2003) and also from The Compendium of Pesticide Common Names,
http://www.alanwood.net/pesticides/.

Preferred dinitroaniline herbicides include prodiamine, oryzalin, pendimethalin and
trifluralin and their salts, as well as mixtures thereof.
In particular preferred compositions of this embodiment, the herbicide B comprises or
in particular is prodiamine.
In other particular preferred compositions of this embodiment, the herbicide B com-
prises or in particular is oryzalin.
In further particular preferred compositions of this embodiment, the herbicide B com-
prises or in particular is pendimethalin, which is a particular preferred composition of
the present invention.
In further particular preferred compositions of this embodiment, the herbicide B com-
prises or in particular is trifluralin.
In this embodiment the relative weight ratio of pyroxasulfone and dinitroaniline herbi-
cide is preferably from 100:1 to 1:500 and more preferably from 50:1 to 1:300.
The rate of application of pyroxasulfone is usually from 1 g/ha to 500 g/ha and prefera-
bly in the range from 5 g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active substance
(a.s.).
The rate of application of the dinitroanilines is usually from 10 g/ha to 5000 g/ha and
preferably in the range from 50 g/ha to 4000 g/ha or from 100 g/ha to 2500 g/ha of ac-
tive substance (a.s.).
The compositions of this embodiment are particularly suitable for controlling mono- and
dicotyledonous weeds and sedge weeds, in particular Alopecurus myosuroides, Apera
spica-venti, Brachiaria spec, Digitaria spec, Echinocloa spec, Eleusine spec, Lolium
spec, Phalaris spec, Setaria spec, Amaranthus spec, Anthemis spec, Capsella
bursa-pastoris, Chenopodium spec, Galium aparine, Lamium spec, Matricaria spec,
Papaver rhoeas, Raphanus raphanistrum, Sinapis arvensis, Stellaria media, Thlaspi
arvense, Veronica spec, and Viola spec.
The compositions of this embodiment are in particular suitable for combating undesired
vegetation in wheat, barley, rye, triticale, durum, rice, corn, sugarcane, sorghum, soy-
bean, pulse crops such as pea, bean and lentils, peanut, sunflower, sugarbeet, potato,
cotton, brassica crops, such as oilseed rape, canola, mustard, cabbage and turnip, turf,

grapes, stonefruit, such as peach, almond, walnut, olive, cherry, plum and apricot, cit-
rus and pistachio.
If not stated otherwise, the compositions of this embodiment are suitable for application
in any variety of the aforementioned crop plants.
The compositions of this embodiment are particularly suitable for application in wheat,
barley, rye, triticale, durum, rice, corn, sorghum, sugarcane, soybean, pulse crops,
brassica crops, turf, stonefruit, citrus and grapes.
The compositions of this embodiment can preferably be used in crops which tolerate
and/or are resistant to the action of MTA inhibitor herbicides, preferably in crops which
tolerate and/or are resistant to the action of dinitroanilide herbicides. The resistance
and or tolerance to said herbicides may be achieved by conventional breeding and/or
by genetic engineering methods.
The compositions of the first embodiment may additionally comprise a herbicide D,
which is selected from dimethenamid, dimethenamid-P, flufenacet, metribuzin, flupyr-
sulfuron, picolinafen and prosulfocarb. These compositions are hereinafter also re-
ferred to as compositions of embodiment 1a.
In particular preferred compositions of this embodiment 1a, the herbicide B comprises
or in particular is pendimethalin.
In the compositions of the embodiment 1 a, the weight ratio of pyroxasulfone and the
herbicide D is as given above. Likewise, the application rates of the herbicides D are as
given above.
The compositions of the embodiment 1a can be used for the same purpose as the
compositions of embodiment 1. The compositions of the embodiment 1a are particu-
larly useful for application in crops. They are especially useful for application in corn,
sunflower, soybeans, oilseed rape, potato and small grain cereals, as they provide in-
creased control of undesirable weeds at reduced application rates and thus at reduced
risk of crop damage.
In more preferred compositions of this embodiment 1a, the herbicide B comprises or in
particular is pendimethalin and the herbicide D is metribuzin. These compositions are
also referred to as compositions 1a.2. These compositions are particularly useful for
application in soybean and potato, as they provide increased control of undesirable
weeds at reduced application rates and thus at reduced risk of crop damage.

In particular preferred compositions of this embodiment 1a, the herbicide B comprises
or in particular is pendimethalin and the herbicide D is dimethenamid or dimethenamid-
P. These compositions are also referred to as compositions 1a.1. These compositions
are particularly useful for application in corn, sunflower, oilseed rape and potatoe, as
they provide increased control of undesirable weeds at reduced application rates and
thus at reduced risk of crop damage.
In other particular preferred compositions of this embodiment 1a, the herbicide B com-
prises or in particular is pendimethalin and the herbicide D is metribuzin. These com-
positions are also referred to as compositions 1a.2. These compositions are particularly
useful for application in soybean and potato, as they provide increased control of unde-
sirable weeds at reduced application rates and thus at reduced risk of crop damage.
In other particular preferred compositions of this embodiment 1a, the herbicide B com-
prises or in particular is pendimethalin and the herbicide D is flupyrsulfuron. These
compositions are also referred to as compositions 1a.3. These compositions are par-
ticularly useful for application in small grain cereals, as they provide increased control
of undesirable weeds at reduced application rates and thus at reduced risk of crop
damage.
In other particular preferred compositions of this embodiment 1a, the herbicide B com-
prises or in particular is pendimethalin and the herbicide D is picolinafen. These com-
positions are also referred to as compositions 1a.4. These compositions are particularly
useful for application in small grain cereals, as they provide increased control of unde-
sirable weeds at reduced application rates and thus at reduced risk of crop damage.
In other particular preferred compositions of this embodiment 1a, the herbicide B com-
prises or in particular is pendimethalin and the herbicide D is prosulfocarb. These com-
positions are also referred to as compositions 1a.5. These compositions are particularly
useful for application in small grain cereals, as they provide increased control of unde-
sirable weeds at reduced application rates and thus at reduced risk of crop damage.
In other particular preferred compositions of this embodiment 1a, the herbicide B com-
prises or in particular is pendimethalin and the herbicide D is flufenacet. These compo-
sitions are also referred to as compositions 1 a.6. These compositions are particularly
useful for application in small grain cereals, as they provide increased control of unde-
sirable weeds at reduced application rates and thus at reduced risk of crop damage.

According to a second embodiment of the invention, the component b) comprises at
least one pyridine herbicide. Pyridine herbicides are known from e.g. D. W. Lickfeldt et
al. "Microtubulin Assembly Inhibitors (Pyridines)" in "Modern Crop Protection Com-
pounds" Vol. 1, Wiley-VHC 2007, pp 317-323; C.D.S. Tomlin, "The Pesticide Manual",
13th Edition, BCPC (2003), and The Compendium of Pesticide Common Names
http://www.alanwood.net/pesticides/.
Suitable pyridine herbicides are dithiopyr and thiazopyr and their salts, as well as mix-
tures thereof.
In particularly preferred compositions of this embodiment, the herbicide B comprises or
in particular is dithiopyr. This compound is known e.g. from US 4,692,184 (Monsanto
Company).
In other particularly preferred compositions of this embodiment, the herbicide B com-
prises or in particular is thiazopyr. This compound is known e.g. from US 4,988,384
(Monsanto Company).
In this embodiment the relative weight ratio of pyroxasulfone and pyridine herbicide is
frequently from 500:1 to 1:500, preferably from 250:1 to 1:250, in particular from 100:1
to 1:100.
The rate of application of pyroxasulfone is usually from 1 g/ha to 500 g/ha and prefera-
bly in the range from 5 g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active substance
(a.s.).
The rate of application of the pyridine herbicide is usually 10 to 5000 g/ha, in particular
50 to 2500 g/ha, preferably 100 to 1500 g/ha, of active substance (a.s.).
The compositions of this embodiment are particularly suitable for controlling mono- and
dicotyledonous weeds and sedge weeds, in particular Digitaria spec, Echinocloa
spec, Eleusine spec, Lolium spec, Setaria spec, and polygonum spec.
The compositions of this embodiment are in particular suitable for combating undesired
vegetation in sugarcane, turf, grapes, stonefruit, such as peach, almond, walnut, olive,
cherry, plum and apricot, citrus and pistachio, garden ornamentals, bulb ornamentals,
conifers and deciduous trees.
If not stated otherwise, the compositions of this embodiment are suitable for application
in any variety of the aforementioned crop plants.

The compositions of this embodiment can preferably be used in crops which tolerate
and/or are resistant to the action of MTA inhibitor herbicides, preferably in crops which
tolerate and/or are resistant to the action of pyridine herbicides. The resistance and or
tolerance to said herbicides may be achieved by conventional breeding and/or by ge-
netic engineering methods.
The present invention also relates to formulations of the compositions according to the
present invention. The formulations contain, besides the composition, at least one
organic or inorganic carrier material. The formulations may also contain, if desired, one
or more surfactants and, if desired, one or more further auxiliaries customary for crop
protection compositions.
The formulation may be in the form of a single package formulation containing both the
herbicide A and the at least one herbicide B together with liquid and/or solid carrier
materials, and, if desired, one or more surfactants and, if desired, one or more further
auxiliaries customary for crop protection compositions. The formulation may be in the
form of a two package formulation, wherein one package contains a formulation of py-
roxasulfone while the other package contains a formulation of the at least one herbicide
B and wherein both formulations contain at least one carrier material, if desired, one or
more surfactants and, if desired, one or more further auxiliaries customary for crop pro-
tection compositions. In the case of two package formulations the formulation contain-
ing pyroxasulfone and the formulation containing the herbicide B are mixed prior to
application. Preferably the mixing is performed as a tank mix, i.e. the formulations are
mixed immediately prior or upon dilution with water. If the composition comprises one
or more further actives such as a safener C and/or a herbicide D, the composition may
also be in the form of a three or four package formulation.
In the formulation of the present invention the active ingredients, i.e. pyroxasulfone,
herbicide B and optional further actives are present in suspended, emulsified or dis-
solved form. The formulation according to the invention can be in the form of aqueous
solutions, powders, suspensions, also highly-concentrated aqueous, oily or other sus-
pensions or dispersions, aqueous emulsions, aqueous microemulsions, aqueous
suspo-emulsions, oil dispersions, pastes, dusts, materials for spreading or granules.
Depending on the formulation type, they comprise one or more liquid or solid carriers, if
appropriate surfactants (such as dispersants, protective colloids, emulsifiers, wetting
agents and tackifiers), and if appropriate further auxiliaries which are customary for
formulating crop protection products. The person skilled in the art is sufficiently familiar

ganic thickeners, bactericides, antifreeze agents, antifoams, colorants and, for seed
formulations, adhesives.
Suitable carriers include liquid and solid carriers. Liquid carriers include e.g. non-
aqueous solvents such as cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahy-
dronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and
their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohex-
anol, ketones such as cyclohexanone, strongly polar solvents, e.g. amines such as N-
methylpyrrolidone, and water as well as mixtures thereof. Solid carriers include e.g.
mineral earths such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk,
bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate,
magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate,
ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin
such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders,
or other solid carriers.
Suitable surfactants (adjuvants, wetting agents, tackifiers, dispersants and also
emulsifiers) are the alkali metal salts, alkaline earth metal salts and ammonium salts of
aromatic sulfonic acids, for example lignosulfonic acids (e.g. Borrespers-types,
Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo
Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), and of fatty acids,
alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol
sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol
glycol ethers, condensates of sulfonated naphthalene and its derivatives with
formaldehyde, condensates of naphthalene or of the naphthalenesulfonic acids with
phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-,
octyl- or nonylphenol, alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyether
alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated
castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol
polyglycol ether acetate, sorbitol esters, lignosulfite waste liquors and proteins,
denaturated proteins, polysaccharides (e.g. methylcellulose), hydrophobically modified
starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE,
Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, Lupamine types),
polyethyleneimine (BASF SE, Lupasol types), polyvinylpyrrolidone and copolymers
thereof.
Examples of thickeners (i.e. compounds which impart to the formulation modified flow
properties, i.e. high viscosity in the state of rest and low viscosity in motion) are
polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone
Poulenc) or Veegum® (from R.T. Vanderbilt), and also organic and inorganic sheet

minerals, such as Attaclay® (from Engelhardt).
Examples of antifoams are silicone emulsions (such as, for example, Silikon® SRE,
Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty
acids, organofluorine compounds and mixtures thereof.
Bactericides can be added for stabilizing the aqueous herbicidal formulations.
Examples of bactericides are bactericides based on diclorophen and benzyl alcohol
hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK
from Rohm & Haas), and also isothiazolinone derivates, such as alkylisothiazolinones
and benzisothiazolinones (Acticide MBS from Thor Chemie).
Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
Examples of colorants are both sparingly water-soluble pigments and water-soluble
dyes. Examples which may be mentioned are the dyes known under the names
Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1, and also pigment blue
15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80,
pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red
48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34,
pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown
25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9,
acid yellow 23, basic red 10, basic red 108.
Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol
and tylose.
To prepare emulsions, pastes or oil dispersions, the active the components, as such or
dissolved in an oil or solvent, can be homogenized in water by means of wetting agent,
tackifier, dispersant or emulsifier. Alternatively, it is possible to prepare concentrates
consisting of active substance, wetting agent, tackifier, dispersant or emulsifier and, if
desired, solvent or oil, and these concentrates are suitable for dilution with water.
Powders, materials for spreading and dusts can be prepared by mixing or concomitant
grinding of the active the components a) and b) and optionally safener c) and/or herbi-
cide D with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules,
can be prepared by binding the active ingredients to solid carriers.

The formulations of the invention comprise a herbicidally effective amount of the com-
position of the present invention. The concentrations of the active the active ingredients
in the formulations can be varied within wide ranges. In general, the formulations com-
prise from 1 to 98% by weight, preferably 10 to 60 % by weight, of active ingredients
(sum of pyroxasulfone, herbicide B and optionally further acitves). The active ingredi-
ents are employed in a purity of from 90% to 100%, preferably 95% to 100% (according
to NMR spectrum).
The active compounds A and B and the optionally further actives as well as the com-
positions according to the invention can, for example, be formulated as follows:
1. Products for dilution with water
A Water-soluble concentrates
10 parts by weight of active compound (or composition) are dissolved in 90 parts by
weight of water or a water-soluble solvent. As an alternative, wetters or other adjuvants
are added. The active compound dissolves upon dilution with water. This gives a
formulation with an active compound content of 10% by weight.
B Dispersible concentrates
20 parts by weight of active compound (or composition) are dissolved in 70 parts by
weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for
example polyvinylpyrrolidone. Dilution with water gives a dispersion. The active
compound content is 20% by weight.
C Emulsifiable concentrates
15 parts by weight of active compound (or composition) are dissolved in 75 parts by
weight of an organic solvent (eg. alkylaromatics) with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
Dilution with water gives an emulsion. The formulation has an active compound content
of 15% by weight.
D Emulsions
25 parts by weight of active compound (or composition) are dissolved in 35 parts by
weight of an organic solvent (eg. alkylaromatics) with addition of calcium
dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
This mixture is introduced into 30 parts by weight of water by means of an emulsifier
(Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an
emulsion. The formulation has an active compound content of 25% by weight.

E Suspensions
In an agitated ball mill, 20 parts by weight of active compound (or composition) are
comminuted with addition of 10 parts by weight of dispersants and wetters and 70 parts
by weight of water or an organic solvent to give a fine active compound suspension.
Dilution with water gives a stable suspension of the active compound. The active
compound content in the formulation is 20% by weight.
F Water-dispersible granules and water-soluble granules
50 parts by weight of active compound (or composition) are ground finely with addition
of 50 parts by weight of dispersants and wetters and made into water-dispersible or
water-soluble granules by means of technical appliances (for example extrusion, spray
tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the
active compound. The formulation has an active compound content of 50% by weight.
G Water-dispersible powders and water-soluble powders
75 parts by weight of active compound (or composition) are ground in a rotor-stator mill
with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with
water gives a stable dispersion or solution of the active compound. The active
compound content of the formulation is 75% by weight.
H Gel formulations
In a ball mill, 20 parts by weight of active compound (or composition), 10 parts by
weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water
or of an organic solvent are mixed to give a fine suspension. Dilution with water gives a
stable suspension with active compound content of 20% by weight.
2. Products to be applied undiluted
I Dusts
5 parts by weight of active compound (or composition) are ground finely and mixed
intimately with 95 parts by weight of finely divided kaolin. This gives a dusting powder
with an active compound content of 5% by weight.
J Granules (GR, FG, GG, MG)
0.5 parts by weight of active compound (or composition) are ground finely and
associated with 99.5 parts by weight of carriers. Current methods here are extrusion,
spray-drying or the fluidized bed. This gives granules to be applied undiluted with an
active compound content of 0.5% by weight.
K ULV solutions (UL)

10 parts by weight of active compound (or composition) are dissolved in 90 parts by
weight of an organic solvent, for example xylene. This gives a product to be applied
undiluted with an active compound content of 10% by weight.
Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes,
wettable powders or water-dispersible granules by adding water.
It may furthermore be beneficial to apply the compositions of the invention alone or in
combination with other herbicides, or else in the form of a mixture with other crop
protection agents, for example together with agents for controlling pests or
phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt
solutions, which are employed for treating nutritional and trace element deficiencies.
Other additives such as non-phytotoxic oils and oil concentrates may also be added.
Use Examples
The effect of the herbicidal compositions according to the invention of herbicides A and
B and, if appropriate, safener on the growth of undesirable plants compared to the her-
bicidally active compounds alone was demonstrated by the following greenhouse ex-
periments:
For the pre-emergence treatment, directly after sowing the active compounds, which
had been suspended or emulsified in water, were applied by means of finely distributed
nozzles. The containers were irrigated gently to promote germination and growth and
subsequently covered with transparent plastic hoods until plant had rooted. This cover
caused uniform germination of the tests plants, unless this was adversely affected by
active compounds.
For the post-emergence treatment, the test plants were first grown to a height of 3 to
20 cm, depending on the plant habit, and only then treated. Here, the herbicidal com-
positions were suspended or emulsified in water as distribution medium and sprayed
using finely distributing nozzles.
The respective herbicides A and/or safener were formulated as 10% by weight strength
suspension concentrate and introduced to the spray liquor with the amount of solvent
system used for applying the active compound. Herbicide B and/or safener were used
as commercially available formulations and introduced to the spray liquor with the
amount of solvent system used for applying the active compound. In the examples, the
solvent used was water.

Pendimethalin was used as a commercial aqueous suspension concentrate having an
active ingredient concentration of 400 g/l.
The test period extended over 21 days. During this time, the plants were tended, and
their response to the treatments with active compound was evaluated.
The evaluation for the damage caused by the chemical compositions was carried out
using a scale from 0 to 100%, compared to the untreated control plants. Here, 0 means
no damage and 100 means complete destruction of the plants.
The plants used in the greenhouse experiments belonged to the following species:

Colby's formula was applied to determine whether the composition showed synergistic
action. The value E, which is to be expected if the activity of the individual compounds
is just additive, was calculated using the method of S. R. Colby (1967) "Calculating
synergistic and antagonistic responses of herbicide combinations", Weeds 15, p. 22 ff.

VO 2009/112486 PCT/EP2009/052782
25
E = X + Y-(XY/100)
where X = effect in percent using herbicide A at an application rate a;
Y = effect in percent using herbicide B at an application rate b;
E = expected effect (in %) of A + B at application rates a + b.
If the value observed in this manner is higher than the value E calculated according to
Colby, a synergistic effect is present.
An accelerated activity is observed when the damage 7 or 8 days after treatment (7
DAT or 8 DAT) achieved by the combination shows a synergistic effect.
Table 1 a relates to the herbicidal activity of the individual actives in pre-emergence
application assessed 8 DAT and 20 DAT. Table 1b relates the herbicidal activity of the
combined actives in pre-emergence application assessed 8 DAT and 20 DAT.
Table 2a relates to the herbicidal activity of the individual actives in post-emergence
application assessed 7 DAT and 20 DAT. Table 2b relates the herbicidal activity of the
combined actives in post-emergence application assessed 7 DAT and 20 DAT.
Table 3 relates to the herbicidal activity of the individual actives and of the combina-
tions in post-emergence application assessed 20 DAT.
Table 1a: Application in Pre-Emergence of pyroxasulfone and pendimethalin
(individual activities)

Table 1b: Application in Pre-Emergence of pyroxasulfone and pendimethalin
(combined activities)

Table 2a: Application in Post-Emergence of pyroxasulfone and pendimethalin
(individual activities)

5 Table 2b: Application in Post-Emergence of pyroxasulfone and pendimethalin
(combined activities)

Table 3: Application in Post-Emergence of pyroxasulfone and pendimethalin

1) observed activity in % destruction 20 days after treatment
2) calculated from the individual activities by Colby's formula
3) Synergism: Y = Yes; N = No

We claim:
1. A herbicidal composition comprising:
a) a herbicide A which is 3-[5-(difluoromethoxy)-1-methyl-3-
(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-
oxazole;
and
b) at least one herbicide B which is an inhibitor of microtubule assembly.
2. The composition as claimed in claim 1, wherein the herbicide B comprises at
least one herbicide selected from the group of dinitroanilines.
3. The composition as claimed in claim 2, wherein the herbicide B is selected from
the group of prodiamine, oryzalin, pendimethanlin and trifluralin.
4. The composition as claimed in claim 2, wherein the herbicide B comprises
pendimethalin.
5. The composition as claimed in claim 2, wherein the herbicide B comprises
prodiamine.
6. The composition as claimed in claim 2, wherein the herbicide B comprises
oryzalin.
7. The composition as claimed in claim 2, wherein the herbicide B comprises triflu-
ralin.
8. The composition as claimed in any of claims 2 to 7, additionally comprising a
herbicide D, which is selected from the group consisting of dimethenamid, di-
methenamid-P, flufenacet, metribuzin, flupyrsulfuron, picolinafen and prosulfo-
carb.
9. The composition as claimed in claim 1, wherein the herbicide B comprises at
least one herbicide selected from the group of pyridine herbicides.
10. The composition as claimed in claim 9, wherein the herbicide B is selected from
the group of dithiopyr and thiazopyr.

11. The composition as claimed in any of the preceding claims, containing no
safener.
12. The composition as claimed in any of the preceding claims, wherein the relative
amount of herbicide A to the at least one herbicide B is from 250:1 to 1:250.
13. The use of the compositions as claimed in any of the preceding claims for con-
trolling undesirable vegetation.
14. The use as claimed in claim 13 for controlling undesirable vegetation in crop
plants.
15. The use as claimed in claim 14, wherein the crop plants are crops of wheat, bar-
ley, rye, triticale, durum, rice, corn, sugarcane, sorghum, soybean, pulse crops,
peanut, sunflower, sugarbeet, potato, cotton, brassica crops, turf, grapes, pome-
fruit, stonefruit, citrus, coffee, pistachio, garden ornamentals, bulb ornamentals,
conifers and deciduous trees.
16. The use of a composition as claimed in any of claims 1 to 12 for controlling unde-
sirable vegetation in crop plants, where the crop plants are resistant to herbicides
acting as an inhibitor of microtubule assembly.
17. A method for controlling undesirable vegetation, which comprises allowing a
composition as claimed in any of claims 1 to 12 to act on plants to be controlled
or their habitat.
18. The method as claimed in claim 16, which comprises applying the composition as
claimed in claims 1 to 12 before, during and/or after the emergence of the unde-
sirable plants; the herbicides A and B being applied simultaneously or in succes-
sion.
19. An herbicide formulation comprising a composition as claimed in any of claims 1
to 12 and at least one solid or liquid carrier.

The present invention relates to herbicidally active compositions, which comprise 3-[5- (difluoromethoxy)-1
-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro- 5,5-dimethyl-l,2-oxazole [common name pyroxasulfone]
and at least one herbicide B, which is an inhibitor of microtubule assembly. The invention furthermore relates to the use of a composition
as defined herein for controlling undesirable vegetation in crops. When using the compositions of the invention for this
purpose the herbicide A and the at least one herbicide B can be applied simultaneously or in succession in crops, where undesirable
vegetation may occur.