Note : Les descriptions sont présentées dans la langue officielle dans laquelle elles ont été soumises.
_~.
~488QS
O.Z. 30,354
HERBICIDE
The present ir.vantion relates to a herbicide comprising a
composition of active in~redients. It is known that benzothia-
diazinone dioxides and substituted urea derivatives have a
herbicidal action. However, this actior. is not always satis-
factory.
We have now fourd that a compositior. of
a) a compound of the formula
o
Rl
,S2
H
where Rl denotes lower alkyl, or a sal~ thereof,
and
b) a urea derivative selected from the group consisting
of N-3-chloro-4-isopropylphenyl-N~-methyl-N~-methoxy-
urea, 1~'-3-methyl-4-bromophenyl-NI,N~-dimethylurea,
N- [4-(4'-chlorophenoxy)-pher.yl~ ',N'-dimethylurea,
N-3-methyl-4-chlorophenyl-N',N'-dimathylurea ard
N- ~-(4'-mathoxyphenoxy)-phenyl~-N',N'-dimethylurea
-- 1 --
,~'''
. ,,
,
10488~5 Z 30,354
has a better herbicidal actior. than its components.
The compositions may contain one or more compounds of the
formula a and of the formula b.
The ratio oP the active ingredients to each other may be
selected at will, fro~ 0.1 to 10 ~arls bv wei~ht of a to 1
part by weight of b, and preferably from 0.3 to
3 parts by weight of a to 1 part by weight of b.
The amour.t usad of tha agents according to the ir-.vention
may vary and depends in esser.ce on the typa Or effect to be
achieved; it is generally from 0.1 to ~0 (ar.d more), prefer-
ably from 0.2 to ~, kg per hectare of active ingrediert. The
agents according to the invention may be used once or several
times ba~ore or after planting, before sowing, and before,
during or after emargence of the crop plants and ur.wanted
plants.
The compositions are selective ir. Triticum aestivum, Hor-
deum vulgare, Secale cereale, Zea mays, Sorghum spp., Glycine
max., Pisum sativum, Solanum tuberosum, and other crops.
The compositions may also be used as total herbicides on
ditches, aquatic areas, railroad tracks, and barren or waste
land, etc.
Applica~ion may be effected for instance in the form of
directly sprayable solutions, powders, suspensions, disper-
sions, emulsions, oil dispersions, pastes, dusts, broadcast-
ing agents, or granules by spraying, atomizing, dustir.g,
broadcasting or watering. The forms of application depend en-
tirely on the purpose for which the agents are bair.g used, in
any case they should er.sure a fine distribution of the active
ingredient.
~48805 o . z 30,354
For the preparation of solution~, emulsion~, pastes and
oil dispersions to be sprayed direct, mineral oil fractions of
medium to high boiling point, such as kerosene or die~el oil,
further coal-tar oils, etc. and oils of vsgetable or mineral
origin, aliphatic, cyclic and aromatic hydrocarbons such a~
benzene, toluene, xylene, paraffin, tetrahydronaphthalene,
alkylated naphthalenes and their derivatives such as methanol,
ethanol, propanol, butanol, chloroform, carbon tetrachloride,
cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc.,
and strongly polar solvents such as dimethylformamide, dimethyl
sulfoxide, N-methylpyrrolidone, water, etc. are suitable.
Aqueous formulations may be prepared from emulsion con-
centrates, pastes, oil dispersions or wettable powders 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. Concentrate~ which are
suitable for dilution with water may be prepared from active
ingredient, 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, naph-
thalenesulfonic acids, phenolsulfonic acids, alkylaryl sul-
fonates, alkyl sulfates, and alkyl sulfonates, alkali metal
and alkaline earth metal salts of dibutylnaphthalenesulfonic
acid, lauryl ether sulfate, fatty alcohol sulfates, alkali
metal and a~kaline earth metal salts of fatty acids, salts
of sulfated hexadecanols, heptadecanols, and octadecanols,
salts of sulfated fatty alcohol glycol ether, condensation
- 3
.
,
: .
~0488~5 z 30~354
products of sulfonated naphthalena and naphthale-re derivati-
ves with formaldehyde, condensation products of naphthaler.e
or naphthalenesulfonic acids with phenol and formaldehyde,
polyoxyethylene octylphenol ethers, ethoxylated isooctyl-
phenol, 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 polyoxypropyl-
ene, lauryl alcohol polyglycol ether acetal, sorbitol esters,lignin, sulfite waste liquors and methyl cellulose.
~ owders, dusts and ~roadcasting agents may be prepared
by mixing or grinding the active ingredients wlth a solid
carrier.
Granules, e.g., coated, impregnated or homogeneous gra-
nules, may be prepared by bonding the active ingredients to
solid carriers. Example~ of solid carriers are mineral earths
such as silica gel, silicic acid, silica gels, silicates,
talc, kaolin, Attaclay, limestone, lime, chalk, bole, loess, ~ -
clay, dolomite, diatomaceous earth, calcium sulfate, magne-
sium sulfate, magnesium oxide, ground plastics, fertilizers
such as ammonium sulfate, ammonium phosphate, ammonium nitra-
te, and ureas~ 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 preferably
0.5 to 9r % by weight of active ingredient. --
There may ~e added to the compositions or individual
active ingredients (if desired, immediately before use (tank-
- 4 -
1~48~5 ~ Z. 30,354
mix)) oils of various types, herbicides, fungicides, nemato-
cides, insecticides, bactericides, trace elements, fertili-
zers, antifoams (e.g., silicones~, ~rowth regulators, anti-
dotes and other herbicidally effective compounds such as
substituted anilines
substituted aryloxycarboxylic acids and salts, esters and
amides thereof,
substituted ethers
substituted arsonic acids and their salts, esters and amides
substituted benzimidazoles
substituted benzisothiazoles
substituted benzothiadiazinone dioxides
gubstituted benzoxazines
substituted benzoxazinones
substituted benzothiadiazoles
substituted biurets
substituted quinolir.es ~ -
substituted carbamates
substituted aliphatic carboxylic acids and their salts, esters
and amides
substituted aromatic carboxylic acids and their salts, esters
and amides
substituted carbamoylalkylthiol- or -dithiophosphates
substituted quinazolines
substituted cyaloalkylamidocarbothiolic acids and their salts,
esters and amides
substituted cycloalkylcarbonamidothiazoles
sub3tituted dicarboxylic acids and t~eir salts, esters and
amides
' ' ' ~,. ' ,
' ~
1048805 o z 30 354
substituted dihydrobenzofuranyl sulfonates
substituted disulfide~
substituted dipyridylium salts
substituted dithiocarbamates
sub~tituted dithiophosphoric acids and their salts, estQrs
and amides
substituted ureas
substituted hexahydro-lH-carbothioates
substituted hydantoins
substituted hydrazides
substituted hydrazonium salts
substituted isoxazole pyrimidones
&ubstituted imidazoles
substituted isothiazole pyrimidones
substituted 4,etones
substituted naphthoquinones
subst~tuted aliphatic nitriles
substituted aromatic nitriles
substituted oxadiazoles
substituted oxadiazinones
substituted oxadiazolidine diones
substituted oxadiazine diones
substituted phenols and their salts and esters
substituted phosphonic acids and their salts, esters and
amides
substituted phosphonium chlorides
substituted phosphonalkyl glycines
substituted phosphites
~ubstituted phosphoric acids and their salts, esters and
30 amides - 6 -
1~488~S Z~ 3~354
substituted piperidines
substituted pyrazoles
substituted pyrazole alkylcarboxylic acids and their salts,
esters and amides
substituted pyrazolium salts
substituted pyrazolium alkyl sulfates
substituted pyridazines
substituted pyridine carboxylic acids and their salts, esters
and amides
substituted pyridines
substituted pyridine carboxylates
substituted pyridinones
substituted pyrimidines
substituted pyrimidones :
substituted pyrrolidine carboxylic acid and its salts, esters
and amides
substituted pyrrolidines
substituted pyrrolidones
substituted arylsulfonic acids and their salts, esters and
amides
substituted styrenes
substituted tetrahydrooxadiazine diones
substituted tetrahydroxadiazole diones -~
substituted tetrahydromethanoindenes
substituted tetrahydroxadiazole thiones
substituted tetrahydrothiadiazine thlones
substituted tetrahydrothiadiazole diones
substituted aromatic thiocarbonylamides
- 7 -
- . . ..
1~488~S 0 z 30 354
substituted thiocarboxylic acids and their salts, esters and
amides
substituted thiol carbamates
substituted thioureas
substituted thiophosphoric acids and their salts, esters and
amides
substituted triazines
substituted triazoles
substituted uracils, and
substituted uretidine diones.
The last-mentioned herbicidal compounds may also be ap-
plied before or after the active ingredients or compositions
thereof according to the invention.
TheRe agents may be added to the herbicides according to
the invention in a ratio by weight of from 1:10 to 10:1. The
same applies to oils, fungicides, nematocides, insecticides,
bactericides, antidotes and growth regulators.
The new compo~ition~ have a strong herbicidal action and
may therefore be used as weedkillers or for controlling the
growth of unwanted plants. Whether the new active ingredients
are used as total or selective agents depends in essence on
the amount of ingredient used per unit area.
By weeds and unwanted plant growth are meant all mono-
cotyledonou~ and dicotyledonous plants which grow in loci
where they are not desired.
The agents according to the invention may therefore be
used for controlling for instance
Gramineae, such as
Cynodon spp. Dactylis spp.
-- 8 --
-
~04~8QS o z 30,354
Digitaria spp. Avena spp.
Echinochloa spp. Bromus spp.
Setaria spp. Uniola spp.
Panicum spp. Poa spp.
Alopacurus spp. Leptochloa spp.
Lolium spp. Brachiaria spp.
Sorghum spp. Eleusine spp.
Agropyron spp. Cenchrus spp.
Phalaris spp. Eragrostis spp. :
Apera spp. Phragmitres communis
etc.;
Cyperaceae, such as
Carax spp. Eleocharis spp.
Cyperus spp. Scirpus spp.
etc.;
dicotyledonous weeds, such as
Ma~vaceae, e.g.,
Abutilon theoprasti Hibiscus spp.
Sida spp. Malva spp.
atc.,
Compositae, such as
Ambrosia spp. Centaurea ~pp.
Lactuca spp. Tussilago spp.
Senecio spp. Lapsana communis
Sonchus spp. Tagetes spp. .
Xanthium spp. Erigeron spp.
Iva spp. Anthemis spp.
Galinsoga spp. Matrica~ia spp. :-
_ 9 _
. . . . . .
.
10488Q5
O.Z. 30,35
Taraxacum spp. Artamisia 8pp.
Chrysanthemum spp. ~idens spp.
Cirsium spp. etc.;
Convolvulaceae, such as
Convolvulus spp. Cuscuta spp.
Ipomea spp. Jaquemontia tamnifolia
etc.;
Cruciferae, such as
Barbaraa vulgaris Arabidopsis thaliana
Brassica spp. Dascurainia spp.
Capsella spp. Draba spp.
Sisymbrium spp. Coronopus didymus
Thlaspi spp. Lepidium spp.
Sinapis arvensis Raphanus spp.
etc.;
Geraniaceae, such as
Erodium spp. Geranium spp.
~tc.;
Portulac~ceae, such as
Portulaca spp. etc.;
Primulaceae, such as
Anagallis arvensis Lysimachia spp.
etc.
Rubiaceae, ~uch as
Richardia spp. Diodia spp.
Galium spp. etc.;
Scrophulariaceae, such as
Linaria spp. Digitalis spp.
-- 10 --
1~)488Q5
0.~. 30,354
Veronica spp. etc.;
Solanaceae, such as
Physalis spp. Nicandra 5pp.
Solanum spp. Datura 3pp.
etc.j
Urticaceae, such as
Urtica spp.
Violaceae, such as
Viola spp. etc.;
Zygophyllaceae, such as
Tribulus terrestris etc.;
Euphorbiaceae, such as ~ -
Mercurialis annua Euphorbia spp.
Umbelliferae, such as
Daucus carota Ammi majus
Aethusa cynapium etc.;
Commelinaeae, such as
Commelina spp. etc.;
Labiatae, such as
Lamium spp. Galeopsis spp.
etc.;
Leguminosae, such as
Madicago spp. Sesbania exaltata
Trifolium spp. Cassia 5pp-
Vicia spp. Lathyrus spp.
etc.;
Plantaginaceae, such as
Plantago spp. spp.
: :
10488Q5
O.Z. 30,354
Polygonaceae, such as
Polygonum spp. Fagopyrum spp.
Rumex 8pp . etc.;
Aizoaceaa, such as
Mollugo verticillata etc.;
Amaranthaceae, such as
Amaranthus spp. etc.;
Boraginaceae, such as
Amsinckia spp. Anchusa spp.
Myostis spp. Lithospermum spp.
etc.;
Caryophyllaceae, such as
Stellaria 8pp. Silene 8pp.
Spergula spp. Cerastium spp.
Saponaria 8p,p- Agrostemma githago
Scleranthus annuus etc.;
Chenopodiaceae, suc~l as
Chenopodium spp. Atriplex spp.
Kochia spp. Monolepsis nuttalliana
Salsola Kali etc.;
Lythraceae, such as
Cuphea spp. etc.;
Oxalidaceae, such as
~xalis 8pp.
Ranunculaceae, such as
Ranunculus spp. Adonis spp.
Delphinium spp. etc.;
Papaveraceae, such as
Papaver spp. ~'umaria officinalis
etc.; - 12 -
1~488QS ~ z 30 354
~nagraceae, such as
Jussiaea spp. etc.;
~osaceae, such as
Alchemillia spp. Potentilla spp.
etc.;
Potamogetonaceae, ~uch as
Potamogeton spp. etc.;
Najadaceae, such as
Naja~ 8pp . etc.;
10 Equisetaceae
Equis4tum spp. etc.;
Marsileaceae, such as
Marsilea quadrifolia etc.;
~olypodiaceae,
Pteridium quilinum
Alismataceae, such as
Alisma spp. ~agittaria sagittifolia
~tc.
In the greenpouse and in the open, compositions of the
following compounds ware tested on the abovementioned plants.
The action of these compositions correspond to that of the
compositions in Examples 1 to 3;
SO2
R
R1 R2
H CH3
- 13 -
.
.. . .
.
1~488~5 o z. 30,354
Na CH3
(CH3CH2)3NH
/ C 3
Cl CH2-CH -N _ CH "
CH3
/ CH3
Cl CH2 CH2 N \ NH2
CH3
(CH3)2 NH2
(CH3 CH2)2 NH2
(HO CH2 CH2)2-NH2
~iO CH2 CH2-N~ "
C4 Hg ~. NH3
CH2 Cl
H -CH-c~2-cH3
H 4 9
Na
(CH3)2 NH2
HO-CH2-CH2)2 NH2
CH3
Na CH2-CH-C2H5
CH3
H CH-CH-(CH3)2
~ C2H5
H CH
C2H5
Na
( 3)2 2
CH3)2-CH-NH
- 14 -
1~488~5 o.z. 30,354 ~ -
/ C2H5
(CH3-CH2-,CH)2 NH2 CH
CH3 C2H5
CH
Na CH-CH2-CH(CH3)2
C, 2H5
Na CH-(CH2)3-CH3
CH3(CH2)9 NH3 C4Hg sec-
CH3(CH2)11 NH3
C13H27 NH3
CH3(CH2)l3 NH3
C16 H33 NH3
CH3(CH2)17 NH3
CH3(CH2)7-CH-cH (CH2)~
cl2_H25_NH ,C, N 3
NH
~ 3
=~
~ 3 ..
W ' .
H C4H9
Na "
(CH3)2 NH2
(HO-CH2-CH2)2 NH2
, 3 , ~:
Cl CH2-CH2-,N-CH
CH3
- 15 -
488~)5
O.Z. 30,354
CH3
C1 CH2-CH2-N-NH2 C4H9
CH3
H C4H9 sac.
Na
Li
(CH3)2 NH2
(HOCH2CH2)2 NH2
(CH3)2 CH-NH3
C3H
NH3
C / CH3
CH3
CH3
(CH2)3-CH3
/r ~ CH3
_JN
CH3
N
C N C12H25
-- 16 --
10~8~0S
O.Z. 30,354
~ ~ 3 7
H 3
~-~ / 3 "
- ~ N ~
C~H15NH3 H ,.
CH3-(CH2)5 N 3 "
CH3-(CH2)3-CH-cH2 NH3
C2H5
ClOH21NH3
.. i .
12 25 3
C13 H37 3
C.2 H25-NH-C-NH3 ..
NH
C14 H29 NH3
C16 H33 NH3
Cl~ H35 NH3 :
Cl~ H37 NH3
~H-NH3 ,,
~ NH3
H2N ~ 17 -
10488~S
~ C3H7 i.
a 3
Li
NH4
1/2 Ca "
1/2 Mg 1'
/ CH3
Cl CH2 CH2 N 3
CH3
/ CH3
Cl CH2 CH2 N ~ NH2
CH3
3)2 NH2
~HOCH2CH2)2 NH2
( CH3CH2CH2 ) 2-NH2
NH2-NH3
CH3-NH3 "
HO-CH2-CH2-NH3
C3H7 i. -NH3
(CH3)2-CH-O-(cH2)3 NH3
;H3_(CH2)3-CH-cH2-o-(cH2)3-NH3
' C2H5
H 3 7
- 1~ --
., , . ~ . .. - :, .
- .,, . - . .. .
- 1~488Q5
O.Z. 30,354
Na 3 7
( 3)3
/ CH3
Cl CH2 CH2-N - CH3
/ CH3
Cl CH2 CH2 ~ 2
(CH3)2 NH2
(HO CH2 CH2)2 NH2
(CH3 CH2)2 NH2
HO-CH2-CH2-NH3
C4H9 n.-NH3 "
H C3H7 i-
Na "
K 1'
H 2 5
Na "
(CH3)3NH
/ CH3
Cl CH2 CH2-N ~ CH3
CH3
/ CH3
Cl CH2-CH2-N ~ NH2
CH3
(CH3)2 NH2
(CH3CH2)2 NH2
- 19 -
. ~ . .
1~488()5
O.Z. 30,354
HO-CH2-CH2)2 NH2 C2H5
3 NH2
CH -CH "
HO-CH2-CH2-NH3 "
C4 Hg n. NH3 "
and
N-3-chloro-4-isopropylphenyl-N'-methyl-N'-methoxyurea
N-3-methyl- 4-bromophenyl-N'-N'-dimethylurea
N- ~-(4l-chlorophenoxy)-;pheny~ -N t ~ N'-dimethylurea
N-3-methyl-4-chlorophenyl-N',N'-dimethylurea
N- C-(4~-methoxyphenoxy)-phenyll-N~,N~-dimethylurea
EXAMPLE
In the greenhouse, various plants were treated at a height
of from 5 to 22 cm with the following amounts of the following
individual active ingredients and compositions thereof as
dispersions or emulsions:
I 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
0.25, 0.5, 0.75 and 1 kg/ha;
II 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
sodium salt, 0.25, 0.5, 0.75 and 1 kg/ha;
III 3-isopropyl-2,1g3-benzothiadiazinone-(4)-2,2-dioxide,
dimethylamine salt, 0.25, 0.5, .T5 and 1 kg/ha;
IV 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
diethanolamine salt, 0.25 0.5, 0.75 and 1 kg/ha;
V N-3-chloro-4-isopropylphenyl-N'-methyl-N'-methoxyurea,
0.25, 0.5, 0.75 and 1 kg/ha;
I+V, II+V, III+V and IV+V each at rate~ of 0.25+0.75, -~
0.75+0.25 and 0.5+0.5 kg/ha. -
- 20 -
' ~ ' , ' ~ ' . ,
1~488QS o.z. 30,354
After 2 to 3 weeks it was ascertained that the compositions
had a better herbicidal action than their components, combined
with the same crop plant compatibility.
'l'he results are given below:
- 21 -
' '
: ~ .
~0~88~5
O. z . 30,354
o o o ~ o U~ o
. Lr\
o o o o ~ U~
. ~ 3 3
H ~
H Il~ O O O Ir~ L~ O O
H O ~\ 1
U~
O O O O O O L~
~1 O O O ~ ~ O O
~1 ~1 ~D `LO
Lr~
t- O O O 0 0~ ~ O
O
H
Lr~ O O O U~ Lr\ Lr~ O
. O
C~J O O O O O O ,~
O
O O O 0 ~0 0 U~
L
: r- ~ O O u~ x) o
O
H
U~ O O O ~ U~ ~ 0~
O
U~
~ ~ O O ~ O O U~
O ~1
0 ~
0
aJ a) :~ ~ oq
rl h O ~,~ ~ O h ~ a~ b0 q~
~d r1 ~ S ~ S S~
q~ bO ~d 0 td E~
h u ~ ~ a) ~1 ~ h ~ ~
O ~ ~ h ~ Q 01 O td ~d ~ p,
~: ~ ~ a~ ~
~ ~ c~ d S~ S ~ ~d O O
r~l ~ ~ a) ~ .C c~
~ ~ ~ ~ C~ O C)
:~ td a) ~ a~
~r~ S ~ ~ td ~ al Q, ~
O h c~ O ~: ~ H 0 0
c~ ~D h O O h ~: ~~ O
c~ ,!t: C~ ~ ¢ ~
- 2 2 - -
.. .. . . . .
~- ~ . . . .
.. : ' ': ' ' :. ,
o.z. 30,354
~Q48B05
o o o o ~ o "~ :,
Il~ 3 3 3
Lrl
~ O O O O O L~ O
O 3 3 ~ 3
P
L~ O O O Lr~ U~ O O ''
O 1~ ~ ~ 1~ ..
I~
~ O O O O ~ O U~
O ~ ~
~1 O O O ~ ~U O Lr
t- O O O t- O ~
O ~3
P
I~ O O O J C~
O ~1~
~U O O O O O ~ U~
.
O
0
~ ~1 ~I h
.,1 ~ ,1 ~
O ~0 rl 0
,. h ~q o ~a
~ <1~ ~ 0 0
,~ h a~ ~ O h
~ ~ ~ So S~
h 0 ~1 a) ~ r-l ~d h td --I
bD ~ :5 h ~d ~ ~q O ~d ~d ~ p,
~ S: ~ ~D 5 ~
.,1 td o E~ ~ h S h ~d O O
~1 ~ ~ O ~ o
Q ~ O ~ o O O E~
~ a~ a~ a~
~1 S Q '~ ~ ~ p, rl h r~
O ~ O S ~ ~ O O
o W h 0 4~ h ~:~1 o ~d ~ O
~: ~: C~ ~ p ~
- 23 -
O.Z. 30,354
~048805
Lr~ O O O O
. . o~
oo
1~ O O O 0~ ~ J O
+. . ~ ~ O~ O
HO O .1
H
~U~
O O O a~ o
. .
00
U~ U~ O O O ~ ~ X~ )
O O t~
U~ U~
P t- ~ O C ~ ~ ~ $
+ OO .1
H
U~ , .
~' O O O O O
............ x) co a~
00
o
O ~0 rl e1 .
~ e ~ ' e
,1 ~ rl ~ O h td ~ bO
S S~
d ~
~ ~a ,~ ~ h cd
b~ ~ ~ ~ O
.~ ~ ~ s~ O e
,~ ~ ~ " :
, q~ c) ~ o o
~ ~ a~
,~ ~ ~ ~ ~ P- ~ F~ rl
o .c ~ ~ O O
c~ b~ ~ o 0~ h s:: ,~ td O
C) ~ ~ c~
- 24 - :
:' ' . , - . .: :
, . ,. : .
., ~.
- -
o.z. 30,~54
~48805
U~U~ o o o C~ ~ o o
o'o t_ X~ o o
~ Ln
~U o o o ~ ~ o o
O O ~1 .1
L~ L~
~ t-- O O O O~ C7~ ~ O
00 ~ t- cO O
U~ O OO ~ O O
. t-~ C~ O :
O .
L~
P ~ ~ O O 0 ~0~ C~ O
~ 00 ~ ~ CJ~ ~O~ -
H
H 1S~ Lf~
~ O O O O O X7
0 0 ~o ct~
g
.,1
~ ,1 ~J h
~1 h a) rl ~ O h td q~ bO 11~
~ .. ~ ~ ~0 ~ ~ C) S ,~
h 0 H ~ H ~d h ~ H
~,1 ~J ¦ E ::1 o h S h ~d O
.~ S ~ ~ ~
O h . ~ H c~ d o
,Y C~. ~ ~
1048805
O.Z. 30,354
EXAMPLE 2
In the grea-nhouse, variou~ plants were treated at a height
of from 5 to 22 cm with the following amounts of the following
individual active ingredients and compositions thereof as dis-
per~ions or emulsions:
I 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
II 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
sodium salt,
III 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
dimethylamine salt,
IV 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
diethanolamir.e salt,
V N-3-chloro-4-isopropylphenyl-N'-methyl-N-methoxyurea
each at rates of 1, 1.5, 2 and 3 kg/ha; ~;
I+V, II+V, III+V and IV+V each at rates of 2+1, 1+2 and
1.5+1.5 kg/ha;
and, for comparison,
VI N-p-chlorophenyl-N',N'-dimethylurea, at rates of 2 and
3 kg/ha;
I+VI and II+VI each at a rata of 1+2 kg/ha.
After 2 to 3 weeks it was ascertained that the compositions
I~V, II+V, III~V and IV+V had better crop plant compatibility
than VI and the compositions I+VI and II+VI, combined with the ~ -
~ame herbicidal action.
The results are given below:
- 26 -
. . ' ~ ''', , ' '
~
o.z. 30,354
11)48805
o o o o U~ o Ln
r~ N O O~
N O O O ~ O U~ Ln
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- 27 --
. -. ~:
o.z. 30,354
1~4880S
o o o o o Lr~ o
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-- 28 -
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o.z. 30,354
8Q5
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- 29 --
o.z. 30~354
1~)48805
H
.~ ~ ~ ~D O O O O O
H 3 L~ ~ O O O O
H ~1 ~ ~1 ~
H~ ~J ~ ~0 Q O O O O
:~ ~ Ir~ 3 0 0 0 0
+ ~1 ~ ~ ~
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O U~ O O O O ~
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-- 30 --
- . . , ': ' ~ . .
-
~0488QS o z 30,354
ExAr1PLE 3
Ir. the greanhous2, various plarts were treated at a height
of from 4 to 20 cm with the following amounts of tha following
individual active ingredier.ts and compositions thereof as
tankmix dispersions or aqueous solutions:
I 3-isopropyl-2,1,3-benzothiadiazinona-(4)-2,2-dioxide,
II 3-isopropyl-2,1,3-benzothiadiazir.one-(4)-2,2-dioxide,
sodium salt,
III 3-isopropyl-2,1,3-benzothiadiazinore-(4)-2,2~dioxide,
dimethylamine salt,
IV 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide 3
diethanolamine salt,
V N-3-methyl-4-bromophenyl-N',N'-dimethylurea
VI N-3-methyl-4-chlorophenyl-N',N'-dimethylurea
each at rates of 0.25, 0.5, 0.75 and 1 k~/ha;
I+V, II+V, II+V, IV+V, I+VI, II+VI, III+VI and IV+VI each at
rates of 0.25+0.75, 0.75~0.25 and 0.5+0.5 kg/ha.
After 2 to 3 weeks i~ was ascartained that the compositions
had a better herbicidal action than their components, combined
with the same crop plant compatibility.
The results are given below:
- 31
: 1~)48805
O. Z . 30,354
~1 O O O N Ir~ 0~ N
L~ '. ~
H O O O O O O L
'J 1~
. OOO U~OOO "
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In .~
N O O ~ O O O ~ . .
O N
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~ ~.0 N
1~ '
t- OOO OOO1`'~\ '
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H O
Il~
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O
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h ~ H o O H ~ h O t~ H
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- 32 -
. .
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1~)488Q5
o.Z. 30,354
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- 33 -
O.Z. 30,354
~048805
.
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- 34 -
.
O.Z. 30,354
1~)48805
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o.z. 30,354
10488~5
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- 36 -
1~488~!!S
O.Z. 30,354
EXAMPLE 4
In the greenhouse, various plants ware treated at a
height of from 4 to 20 cm with the following amounts of the
following individual active ingredients and compositions thereof
as aqueous solutions or dispersior.s:
I 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide
III 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide,
sodium salt
III N- [4-~4'-chlorophenoxy)-pheny~ -N',N'-dimethylurea
each at rates of 1, 1.5, 2 and 3 kg/ha;
I+III and II~III each at rates of ~+1, 1~2-and 1.5+1.5 kg/ha-
After 12 to 17 days it was ascertainad that the
compositions had a better herbicidal action than their
components, combined with the same crop plant compatibility.
The results are given below:
~5~4880~;
o . z . 30, 354
.,~ o ~
~ U~ ~
N t-- O I
H 3 L~
H i~
H . O O O
~1 r~ 3
~ o U~ 0~
~ O O L~
~I I~ J 3
H ~1 Lr\
H 15~
~1 O C~J 3
O
.~
O U~ O
U~ O O
H I~ (~I `O
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O O O
.1 ~
.,1 ~ .
b3 ~I tO '
~ ~X ~ ~ ~
~ .. ~
~ ~ ~ .~ O ~
~1 a~ ~ c) ~: c.) -
a~ ~ o ~ ~ ~ o o ~ ~
c~ ~0 h ~I S:: c) t~ O
~: C) V ~ t~
104t3805
o.z. 30,354
U~
. . o ~ o
~ ~ C~ ~o
HH
~ ~~ O
+l O~ O
H
Lr~O
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o X ~d
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c> t~D ~ ~1 ~ ~ ~d O
¢ ~ C~ ~ 3 ~ ~1 ~
- 39 -
