Agent weedkiller containing derived from benzofuranyl-alkylaminosulfonates.

It is known that the benzofuranylalkylaminosulfonates, pyridazone, carbamates, the thiolcarbamates, substituted fatty acids, the uracils, sulfates pyrazolium, 1 'éthyl-R-benzoyl-n - (3.4-dichlorophenyl) - 2 a-aminopropionate possess herbicidal action. The latter is however not always satisfactory.

It has been found that has improved herbicidal action that the active substances used separately, a mixture containing

a) a compound of the formula

wherein R, R-^ and RG are hydrogen or an aliphatic residue in to optionally substituted by alkoxy or halogen, and

b) a compound of the formula

th - '

wherein X is an amino group, α-hydroxy p, β, βtrichloréthylamino, acetylamino, halogen-acetylamino, aceto-acetylamino, alkyl amino, dialkyl amino, alkoxyalkylamino, adipamic acid ester, dialkyl 1' aminotartronic acid,

HM,

C=r, alkoxy or carboxy-COQR -, wherein R is CH₃ 0

a lower alkyl group, a phenyl radical, hydrogen and salts, Y is chlorine, bromine, or methoxy, Z is hydrogen, halogen, methyl or trifluoromethyl,

compound of the formula

*² VBE1

^{the n} u-O-X-R

/ "

0 Itj

in which R, j is hydrogen, a lower alkyl group; R.₂ is a lower-alkyl group, a phenyl radical optionally substituted by a halogen, a methyl group, a methoxy group d or₂ can also be a radical of amino - or nitrobenzene sulfonyl, a residue of mono -, bi-or tricycloaliphatic; R is a lower alkyl group, optionally substituted alkinyl aleényle or by halogen, wine remains phenyl or benzyl optionally substituted with a halogen, an alkyl group, or may be the remainder

wherein Y is a methyl group " hydrogen; the R ^ is a lower-alkyl group; X is oxygen or sulfur, or

compound of the formula

X

the R-c-c-O R,

iN "

X IS 0

wherein X is hydrogen, halogen; R is an alkyl group, halogen-alkyl, benzamidoxy, benzyl optionally substituted by halogen, methyl, methoxy, halogen-alkyl; the R ^ is alkyl or benzyl optionally substituted with halogen, Rj may also be of the ïydrqgèoe and salts, or

e) a compound of the formula

wherein R is hydrogen, a group a, -dimé-to-polyethylene resins - ^ - acetoxypropionyl, acetyl or

f) the compound

or

g) a compound of the formula

H

' 6 * 5 SAW DEGREES^6:00 5 R - S - 0⁶ 0

within ASY λ* - " THE V 0, 1!

in which R is alkoxy, phenyl optionally substituted by halogen or by lower alkyl.

Preferred are mixtures a + b, a + c, a + d, a + e, a + f, a + g, a + b + c, a + b + d, a + b + e, a + b + f, a + b + g, a + c + d, has + c of Fe, a + c + f, a + c + g, a + d + e, a + d + f, a + d + g, a + e + f, a + e + g, or a + f + g.

The mixtures may contain one or more compounds of the formula (has) and (d) until (grams).

We can choose any weight ratios. The mixing ratio of the active substances with respect to active ingredients (d) to (grams) is from 0.1 to 10 parts by weight of (has) for 1 part by weight of the active ingredients (hr) to (grams), preferably 0.3 to 3 parts by weight of (has) for 1 part by weight of the active ingredients (d) to (grams).

The compounds of the invention can be used in varying amounts. The amount used depends mainly on the type of desired effect. 111st is typically between 0.1 and 30 or more, preferably between 0.2 and 6 kg of active compound per hectare.

The agents of the invention can be applied one or more times before planting, after planting, before seeding, before emergence, after the emergence or during the emergence of the crop plants or undesirable plants.

The compounds may further be used as agents for total fosses, waters, the railroad tracks, on the bare ground, the rare fallow, andc.

The agents are for example useful in the form of solutions, powders, suspensions or dispersions directly sprayable, emulsions, oil dispersions, pastes, dusting agents, agents to spreading or granules by spraying, atomizing, dusting, broadcasting or watering, the application forms depend entirely goals of use; they should in any case ensure fine distribution of the active ingredients of the invention.

For the preparation of solutions, D.* emulsions, pastes and oil dispersions directly pulvéri3ables, use can be made of mineral oil fractions of medium to high boiling point, such as kerosene, or heavy oil, oils from coal tar, and the like, oils of vegetable or animal origin as well as aliphatic hydrocarbons, cyclic and aromatic, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalene, or their derivatives, such as methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, the chlorobenzene derivatives, isophorone, etc, highly polar solvents, for example dimethylformamide, dimethylsulfoxide, n-methyl pyrrolidone, water, andc.

Can be prepared aqueous application forms by adding water to emulsion concentrates, pastes or wettable powders (sprayable powders), oily dispersions. For the preparation of emulsions, pastes or oil dispersions, the substances can be homogenized as it is, or dissolved in a solvent or oil, by means of wetting agents, adhesives, dispersants or emulsifiers. But it is also possible to prepare concentrates suitable for dilution into water from active substance, wetting agent, adhesive, dispersant or emulsifier and, optionally, solvents or oils.

As surfactants, examples: alkali salts, alkaline earth metal salts, ammonium salts of lignin-suifonic acid, the naphthalenesulphonic acids, acids phenol-suifonic, of alkyl-aryl sulfonates, alkyl sulfates, alkyl sulfonates, alkali salts and alkaline earth salts of acid dibutyl naphthalene suifonic, lauryl ether sulfates, fatty alcohol sulfates, salts of alkali and alkaline earth fatty acid, hexadécanols salts, of heptadécanols, octadécanols of sulfated, salts of sulfated fatty alcohol glycol ethers, condensation products of naphthalene sulfone and naphthalene derivatives with formaldehyde, condensation products of naphthalene, or naphthalenesulfonic acids with phenol and formaldehyde, 1' octylphénoléther polyoxyethylene, the isooctylphénol ethoxylated, ethoxylated octylphenol, nonylphenol ethoxylated, the alkylphenol polyglycol ether, of tributylphényle, alkylaryl polyether alcohol the, tridecyl alcohol, the condensate of ethylene oxide and fatty alcohols, - ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, the lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, and methylcellulose sulphited lyes.

Prepared powders and dusting agents and agents to be spread by mixing or milling together the active substances with a solid carrier.

The granules are prepared, for example the coated granules, the granules and the granules homogeneous impregnation by binding the active ingredient to solid supports.

The solid supports - are, for example, mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, attaclay the, limestone, lime, chalk, the bowl, the loess, clay, dolomite, diatomaceous earth, calcium sulfate and magnesium, magnesium oxide, plastics " crushed, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and products of vegetable origin such as cereal flours, tree bark powder, wood and nut shells, cellulose powders and other solid supports.

The compositions contain 0.1 to 95# had weight of active principle, preferably 0.5 to 90 wt. #.

Can be joined to other active compounds to herbicidal compositions or products taken separately, for example oils of various types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilizers, antifoaming products (e.g. silicone), growth regulators, safeners and other herbicidal compounds, as for example substitution derivatives of the following compounds:

- aniline derivatives,

- aryloxycarboxylic acids, their salts, esters and amides,

- ethers,

arsonic compounds - acids, their salts, esters and amides,

- benzimidazole,

- benzisothiazoles .,

- benzothiadiazinone dioxides,

- benzoxazin,

the benzoxazinone -,

- benzothiadiazole derivatives,

a biuret -,

- quinoline,

- carbamate,

- aliphatic carboxylic acids, their salts, esters and amides,

- aromatic carboxylic acids, their salts, esters and amides,

- alkylthio - or dithiophosphates carbamoyl alkyl,

the quinazoline -,

- cycloalkylamidothiocarboxylic acids, their salts, esters and amides,

- cycloalkylcarbonamidothiazols,

- dicarboxylic acids, their salts, esters and amides,

- dihydrobenzofuranylsulfonates,

- disulfides,

- dipyridilium salts,

- dithiocarbamate,

- dithiophosphoric acids, their salts, esters and amides,

- urea,

- hexahydro 1 H-carbothioates,

- hydantoin,

- hydrazide,

- hydrazonium salts,

- isooxazolpyrimidone,

- imidazole,

- isothiazolpyrimidone,

- ketones,

- naphthoquinones,

- aliphatic nitriles,

- aromatic nitriles,

- oxadiazole,

- oxadiazinone,

- oxadiazolidinedione,

- oxadiazinedione,

- phenols, salts and esters,

- phosphonic acids, salts, esters and amides,

- phosphonium chloride,

- alkylglycocolles phosphonic acids,

- phosphite,

- phosphonic acids, salts, esters and amides,

- piperidine,

- pyrazol,

- pyrazolalhylcarboxylic acids, their salts, esters and amides,

- pyrazolium salts,

- aliylsulfates pyrazolium,

- pyridazine derivatives,

- pyridazinone,

- pyridine-earboxylic, their salts, esters and amides,

~pyridine derivatives,

pyridine - carboxylate,

- pyridinone derivatives,

- pyrimidine derivatives,

- pyrimidone derivatives,

- pyrollidine-carboxylic acids, their salts, esters and amides,

- pyrrolidine derivatives,

- pyrrolidine,

- aryl sulfonic acids, their salts, esters and amides,

- styrene,

- tetrahydro-oxadiazinedione,

- tetrahydro-oxadiazoldione,

- tetrahydromethanoindene,

- tetrahydro-diazolthione,

- tétrahydrothiadiazinethione,

the Old ioneétrahydrothiadiaz - T-O,

- aromatic thiocarboxamides,

- thiocarboxylic acids, their salts, esters and amides,

- thiocarbamate,

- thiourea,

thiophosphoric acids -, their salts, esters and amides,

- triazine derivatives,

the triazole -,

- uracil,

" uretidine dione.

They can be added; directly before use (tankmix). Iæs herbicidal agents mentioned last can also be applied before or after each of the active ingredients or mixtures according to the invention.

the addition of these agents herbicide of the present invention can be in a weight ratio of 10 to 1! 10:1. So is the oils, the fungicides, the nematocides, insecticides, bactericides, the antidotes and growth regulators.

The novel mixtures exhibit strong herbicidal action and thus can be used as agents for killing weeds and for combating undesired plant growth, the selective action or total of novel agents of the invention depends essentially on the amount of active ingredient applied per unit area.

By weeds and undesirable plants, is meant the monocotyledonous or dicotyledonous seed plants which grow in locations where. they are undesired.

With the agents of the invention, it is possible for example destroying:

of

the

of

of

of

grasses, as

Jaquemontiatamnifolia

diamondback, as barbaric vulgaris is Brassiea SPPs.

Of Capsella SPPs.

Sisymbrium SPPs.

Thlaspi SPPs.

The Sinapis arvensis CGMS Raphanus SPPs.

of Geraniaceae, as Erodium SPPs.

Geranium SPPs.

of portulaeaeées, as

Portulacais SPPs.

of Primuloceae, as Anagallis arvensis from Rorippa SPPs.

of the Rubiaceae, as Riehardia SPPs.

Gallium SPPs.

of serofulariaeées, as liûaria SPPs.

Veronica beccabunga SPPs.

solanaceae, as angulata SPPs.

Jimsonweed SPPs.

of Urticaceae, as

ïïrtica SPPs.

of golds, as

The Viola SPPs.

of zygophyllacées, as

Tribulusterrestis of Euphorbiaceae, as

Artemisia annua Kercurialis Umbellifera, Daucuscarota as Aethusacynapium of commelinées, as Commelina SPPs.

The Arabidopsis thaliana Descurainia sophioides SPPs. Draba SPPs.

didymusCoronopusIiepidium SPPs.

and other

and other

and other

and other

Diodia SPPs.

and other

Cite SPPs.

and other

Willwill kicandra SPPs.

and other

and other and other Euphoriaprostata SPPs.

Willwill atnrai juices and other AD

and other

of the labiatae, as Lamium SPPs.

^ aleopsis SPPs.

the legumes, Medicago falcata as

Vicia faba SPPs.

Vetch seeds SPPs.

One or more of Sesbania exaltata plantaginacées, as

Plantago major SPPs.

of Polygonaceae, as ofPolygonum SPPs.

Lumeikesi SPPs.

of Aizoaceae, as

Mollugo Pycnanthemum incanum of amaranthacées, as

Amaranth SPPs.

boraginaceae, as Amsinekia SPPs.

the j ^ yostis SPPs.

lithospermum SPPs.

of caryophyllaeées, as Stellaria SPPs.

Spergula SPPs.

Saponins SPPs.

Annuus or Scleranthus chenopodiaceae, as weed Chenopodium SPPs.

Kochia SPPs.

Kali

of the Lythraceae, as

Cuphea SPPs.

of oxalidacées, as

The Oxalis SPPs.

authentic materials, as Ranunculus SPPs.

Larkspur SPPs.

papaveraceae, as said Papaver SPPs.

Fumaria officinalis and other

Trifolium agrarium blackcurrant SPPs.

and other

and other

Fagopyrum SPPs. and other

and other and other

Anchusa SPPs.

and other

Silene SPPs.

Cerastium SPPs. Agrostemmagithago and other

Atriplex SPPs.

Monolepsisnuttaliana and other

and other

Pheasant's eye SPPs.

and other

and other

in primrose, as

Jussiaea SPPs, and other

rosaceae, as

Àlehemillia SPPs. and other

TribuliHerba SPPs.

of potamogetonacées, as

The Potamogeton SPPs. and other

of nagadacées, as

Sajas SPPs. and other

of marsiléacées, as

Marsileaquadrifolla and other

of the Polypodiaceae, as

Pteridlumaguilinum

of alismataeées, as

Alisma plantago SPPs. and other

Sagittariasagittifolia

of équieétacées as

Iquisetaceae SPPs. and other

The compounds of the invention may be used in crops of cereals, as

Of Avena SPPs. Sorghums

Triticum species, Zea

Of Hordeum SPPs. Panicum virgatum miliaceumMærSPômeliaru ^. ^^8W '

in dicotyledonous crops, as

diamondback, e.g.

Irassica SPPs. Baphanus SPPs.

The Sinapis SPPs. Macamide SPPs.

composed of, for example

Lactuca SPPs. Carthamus is SPPs.

From Helianthus SPPs. Willwill scorzonera SPPs.

malvaceae, e.g. Gossyptum hirsutum legumes, for example

The Medicago SPPs. Galactosidases SPPs.

Trifolium agrarium SPPs. Araehis SPPs.

A Pisum SPPs. A glycine max.

of chénopodiaeées, e.g.

The beta vulgaris extract

Spinacia SPPs.

solanaceae, e.g.

In Solanum SPPs, capsicum is armuumNicotiania SPPs.

of the Linaceae, e.g.

linum usitatissimum SPPs.

of umbelliferae, e.g.

Petrosilenum SPPs. ÂpiumgravolensDaucusearota

the Rosaceae, e.g. Fragaria in

cucurbitaceae, e.g.

Cucumis SPPs. Brebissonii SPPs.

liliaceae, e.g.

The Allium SPPs.

of vitaceous, e.g.

Extract of Vitis vinifera

bromeliaceae, e.g.

Pineapple Cucumis sativus.

In the greenhouse and in open ground, has been tested for the following compounds as mixtures on the aforementioned plants:

the R₂ 0 hM₃

Of Rj 0 0 R₃^E 1 * 2^B 3

2

O

ΟΗ ^

O

thereinCOOC ^

Hence he - - - I-IF

"/

01

01

^ Kyi's - C.

χ

The R-c-c-O R * I-yew¹ X O-

O

H

FOR N-N ^ VBE1

THE R -

The agents mentioned have an effect " which is similar to biological mixtures mentioned in the examples 1 to 11•

Example 1

In greenhouse, is filled earth clay pots are created and sandy and seeded seeds of various plants.

Then treating the earth so prepared with the following active ingredients used separately and as mixtures in the form of bis-persion-emulsion:

I the 2.3 d ihydro-to-3.3-to-dimétbyl and 2 a-étiioxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 dihydro-3.3-to-difcéthyl and 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

Y-quinic acid ethyl ester I-ethyl-ïT-to-cycloiiexyltmolcarbamic VI. the 3-cyclohexyl 5.6-trimethylene-uracil

XII as the 2.3 and dicblorallylester n, n diisopropylthiolearbamic

XIII is the 2.3 " 3 a-trichlorallylester n, e diisopropylthiolcarbamic

XIV and the 2.3 dihydro-3" 3 a-diméthy1 and 2 a-méthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

Xv frames the 2.3 dihydro-3.3 " dimethyl 2 a-méthméth.oxybenzofurane-a 5 a-ylméthylaminosulfonate

The I, III, IV, -XIV, with bath respectively 0.5, 0.75, 1, 2 kg/ha and lll, the V, XII as, respectively XIII with 0.5, 1, 1.5 and 2 kg/ha to the I + III-V-+, + + I-III-VI compound, the I + + III-VII below, the I + II + VIII., the II + III-V-+, + + II-III-IV, VII-n + m +, + II-VIII-nor +, + + III-V-XIV and, -XIV + + III-VI., + III-VII-XIV and +, + + the III-VIII-XIV, + + III-V-Xv frames, the III-VI + + Xv frames, + + III-VII-Xv frames, + + III-VIII with Xv frames 0,5 + 0,5 + 1 respectively, 0,5 + 1 + 0,5, 1 + 0,5 + 0,5 deISGylation/ha.

The I + II, II-III which +, + the I-V, II-V with respectively 0 * 5 + 1,5 +, 1, 5 + 0, 5, 1 + 1 kg/ha.

The I-VI +, + II-VI with respectively 0,5 + 1, 1 + ο, 5, 0, 75 + 0, 75 kg/ha to the III-XIV +, + III-Xv frames, a V-XIV +, + V with Xv frames respectively 0, 5 + 1, 5, 1, 5 + 0, 5, 1 + 1 kg/ha.

XIY yi in +, + VI with Xv frames respectively 0,5 + 1, 1 + 0,5, 0, 75 + 0, 75 kg/ha to I-XII as +, I-XIII is +, + II-XII as, II-XIII is +, + XIII-XIV, XIII-XIV and +, + XII as Xv frames, XIII with 0, 5 + 1, 5 + Xv frames respectively, 1, 5 + 0, 5, 1 + 1 kg/ha in the P, has.

After 3 to 4 weeks, it is found that the mixtures show better herbicidal action that the active substances used separately, the compatibility with respect to crop plants being the same.

test results are shown in Table 1 (see

page 32 to 39•

Example 2

In greenhouse, is filled earth clay pots are created and sandy and seeded seeds of various plants.

Then treating the earth so prepared with the following active ingredients used separately and as mixtures in the form of granules.

I the 2.5 " dihydro 3.3-dimethyl 2 a-éthozyben2ofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 and dibydro-to-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

Y étbylester n-ethyl-n-cyclohexylthiolcarbamic VI. the 3-cyclohexyl 5.6-trimethylene-uracil

XII as the 2.3 and dichlorallylester n, n diisopropylthiolcarbamic

XIII is the 2, 3, 3 a-trichlorallylester acid I, n diisopropylthiolcarbamic

XIV and the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

XY-the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-ylméthylaminosulfonate.

The I, ll, lll, XIII with respectively 1, 1.5, 2, 3, 4, 4.5 kg/acre, IV, XIII, XIY, with bath respectively 1, 1.5, 2, 3, 4 kg/acre.

The I + II + therein, + + I-III-VI compound, the I + 1 + 1 + 2 + III-XII with respectively, 1 + 2 + 1, 2 + 1 + 1 kg/ha.

The I + 1 + 1 + 2 + III-XIII with respectively, 1 + 2 + 1, 2 + 1 + 1, + 2 + 1,5 + 1 lg/acre II-III in the Y +, + + II-III-IV, it + 1 + 1 + 2 + m with the III respectively, 1 + 2 + 1, 2 + 1 + 1 kg/ha.

The II + 1 + 1 + 2 + III-XIII with respectively, 1 + 2 + 1, 2 + 1 + 1, + 2 + 1,5 + 1 kg/xiy of Ba + III in an XY, xiy + III-yi in +, + + III-XII as xiy, xiy + III-XIII is +, + + therein an XY-III, III-yi in the XY + +, + + III-XII as an XY, Y + 1 + 1 + 2 + III-XIII with respectively,

1 + 2 + 1, 1 + 2 + 1, 2 + 1 + 1 kg/ha.

The I + II, II-III which +, + I-therein, the II + Y with 2 + 1 respectively, 1 + 2, 2 + 2 kg/ha to yi in the I +, + II-yi in with "5" 1 + 2 respectively 1,5 + 1, + 2 + 1 kg/acre IIY the III, an XY-III +, 2 + 1 + Y with XIY respectively, 1 + 2, 2 + 2 kg/ha to XIY + yj, 1,5 + 1 + XY-yi in "5" respectively with 1 + 2, 2 + 1 kg/ha to I-XII as +, + I-XIII is, + II-XII as, Xl + XIII., XIY XII as +, + XIII. XIY, XY-XII as +, respectively 1, 5 + 1, 5 + XIII with an XY, 2 + 1, 1 + 2, 2 + 2 kg/ha.

Y with respectively 1, 2, 3 and 4 kg/ha in P.A. and for comparison with

Xl 2 a-chioro-to-4.6-diethylamino-a 1, 3, 5 triazine

XI with 2, 3 kg/ha to pp.a.

The I + 1 + 2 kg/ha to XI with pp.a,

test results include at table 2 (see page 40 to 48)

Example 3

In greenhouse, is filled earth clay pots are created and sandy and seeded seeds of various plants.

Then treating the earth so prepared with the following active ingredients used separately and as mixtures in paste form:

I the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylmétbylaminosulfonat th

II to the 2.3 and dibydro-to-3.3 ~âiméthyl and 2 a-étboxybenzofurane-a 5 a-yldiméthylaminosulfonate

1 - III in the phph.ényl-to-4-amino 5 a-ciiloropyridazone - ( 6)

Y-ethyl ester 1 * H acid ethyl-n cyclobexylthiolcarbamic yi in the 3-cyclohexyl 5" 6-trimethylene-uracil

XII as the 2.3 and dichlorallylester n, n diisopropylthiolcarbamic

XIII is the 2, 3, 3 a-trichlorallylester acid 3n, yew and diisopropylthiolcarbamic

XIY the 2.3 and dibydro-to-3.3-to-dimétbyl and 2 a-méthméth.oxybenzof uranium-a 5 a-yldiméthylaminosulfonate

Xv frames the 2.3 dihydro-3.3-to-dimé polyethylene resins and 2 a-wa: X-: ybenzof uranium-a 5 a-ylméthylaminosulfonate

with respectively 0.5, 2, 3 kg/ha.

The I + III-V-+, + + I-III-VI compound, the I + + III-VII below, the I + II + VIII., the II + III-V-+, + + II-III-IV, II-III-XII as + +, + II-III-IIII +, + + a V-XIV-III, III-VI compound-XIV + +, + + III-XII as-XIV, the m-XIV + + as xM, + + III-V-Xv frames, the III-VI + + Xv frames, Xv frames to Xn + w +, + + III-Xv frames as xM with 0,5 + 0,5 + 2 respectively, 0,5 + 2 + 0,5 " 2 + 0,5 + 0,5 kg/ha.

and for comparison with

Xl 2 chloro-4.5 to-diétbylamino-a 1, 3, 5 triazine with 3 kg/ha to the I + II + pp.a. XI with 0,5 + 0,5 + 2 kg/ha to pp.a respectively.

At " 4 to 5 weeks after, it is established that the mixtures have better compatibility with respect to crop plants that the active principle Xl used separately and that mixture I + II + Xl, the herbicidal action being the same.

test results are shown in Table 3 (see page 49 to 52)

Example 4

In greenhouse, is filled earth clay pots are created and sandy and seeded seeds of various plants.

Then treating the earth so prepared with the following active ingredients used separately and as mixtures in the form of oily dispersion:

I the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II * 2.3 dihydro-3.3 - dimethyl-2 a-éthoxybenzofurane-to-5 yl -

diméthylaminosulfonate

V-ethyl ester acid H-ethyl-N-cyclohexylthiolcarbamic VI. the 3-cyclohexyl 5.6-trimethylene-uracil

XII as the 2.3 and dichlorallylester n, n diisopropylthiolcarbamic

XIII is the 2, 3, 3 a-trichlorallylester acid is K, e diisopropylthiolcarbamic

with respectively 0.5, 1 and 2 kg/ha of pp.a *

I-XII as a V + +, V-I-XIII is + +, + + II-XII as a V, II-XIII is a V + +, i + v + vi, I-VI-XII as + +, + + I-XIII is-VI, II-VI compound XII as + +, II-VI compound XIII is + +, + + II-V-VI with 0,5 + 0,5 + 1 respectively, 0,5 + 1 + 0,5, 1 + 0,5 + 0,5 kg/ha. pp.a.

After 3 to 4 weeks, it is found that the mixtures show better herbicidal action that the active substances used separately, the compatibility with respect to crop plants being the same.

Test results include at table 4 (see

page 53 to 55 -)

Example 5

In open ground, treated different plants to a growth height of 2 to 16 cm with the following active ingredients used separately and mixtures in the form of emulsion-to-disper-to-voltage-tankmix;

I the 2.3 and dibydro-to-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 dihydro-3" 3-dimethyl 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyriàazone - (6)

The rearward Iy carbonylaminophényl-to-ii 3-methoxy - (3'-methylphenyl) sulfonylcarbamate

V. 1' ethyl ester is n-ethyl-n-cyclohexylthiolcarbamic VI. the 3-cyclohexyl 5, 6-trimethylene-uracil

VII is 1.2-dimethyl-3.5-to-diphénylpyrazolium-to-methylsulfate YIII 1 'éthy1 n-benzoy1 n - (3.4-dichlorophenyl) - 2 a-aminopropionate IX 4 chloro-hexadiine and 2 a-y1 and 1 - acid ester I-a 3 a-chlorophenylcarbamic

X is the methyl ester of the acid a-chloro-P-- (4 a-ohlorophényl) propionic

XIY the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

XY-the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzof uranium-a 5 a-ylméthylaminosulfonat th

with respectively 0.5, 1, 1.5 and 2 kg/ha of pp.a.

The I + II, I-rearward Iy +, + I-V shape, the I + 7i microRNA, I-YII +, + I-YIII, + I-IX., I-the X +, + the II-III, II-rearward Iy +, + the II-V, II-yi in +, + 7II the II, II-YIII +, + II to IX., II in the X +, + XIY Ill, rearward Iy XIY +, + Y-XIY, XIY + yj, XIYYII +, + XIYYIII, XIY + IX., XIY the X +, + Ill x7, XY-rearward Iy +, + V-Xv frames, an XY + yj, XY-YII +, + YIII Xv frames, an XY + IX., Xv frames respectively + X with the Q "5 + 1,5, 1" and 1 + 1 kg/acre pp.a 5 + 0,5.

At the end of 12 to 16 days, it is found that the mixtures show better herbicidal action that the active substances used separately, the compatibility with respect to crop plants being the same.

Test results are shown in Table 5 (see page 56 to 62)

6 Bxemple

In open ground, treated different plants to a growth height of 2 to 18 cm with the following active ingredients used separately and as mixtures in the form of oily dispersion:

I the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 and djLhydro-a 3.3 -<liméthyl and 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

Uit 3 a-méthoxycarbonylaminophényl-to-M M - (3^, - methylphenyl) sulfonylcarbamate

T the ethyl ester is n-ethyl-n-cyclohexylthiolcarbamic Tl the 3-cyclohexyl 5.6-trimethylene-uracil

The ITR 1.2-dimethyl-3.5-to-diphénylpyrazolium-to-methylsulfate tills 1 'éthyl k-benzoyl ii - (3.4-dichlorophenyl) - 2 a-aminopropionate IX 4 chloro-hexadiine and 2 a-y1-to-1 ester of n-3 a-chlorophenylcarbamic

X is the methyl ester of the acid a-chloro-- (3 - (4-chlorophenyl) propionic acid

The xi7 2.3 dihydro-3.3-to-dimétbyl and 2 a-méthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

The xt is 2.3 dihydro-3.3-to-âiméthyl and 2 a-méthoxybenzofurane-a 5 a-ylméthylaminosulfonate

with respectively 1, 1.5, 2, 3 and 4 kg/ha of pp.a.

THE I + II, I-IT-+, + I-T-, I-TL +, + I-ITR, THE I + TIII REFERS, + I-IX., I-THE X +, + THE II-III, II-IT-+, + T-II WHICH, - 11 + 71, THE II + 7II, THE II + TIII REFERS, THE II + IX., II IN THE X +, + AOGTAO PARKS ILL, AOGTAO PARKS + ITS, T-+ AOGTAO PARKS, TL + AOGTAO PARKS, AOGTAO PARKS + ITR, + AOGTAO PARKS TIII REFERS, . Aogtao Parks + IX., the X + aogtao Parks, xt is + lll, xt is + ITs, xt is T-+, Tl + xt is, xt is + ITR, xt is + TIII refers, x7 + ix, ΧΤ + Χ with respectively 1 + 2, 2 + 1, 1, 5 + 1, 5, 2 + 2, 3 + 1, 1 + 3 kg/ha to pp.a.

and for comparison with

Xi 2 chloro-4.6-diethylamino-a 1, 3, 5 triazine

with 3 kg/ha to pp.a respectively.

The II + 1 + 3 kg/ha in the Xi pp.a.

the Ku-tip 12 to 15 days, it is established that the mixtures have better compatibility with respect to crop plants that the active principle Xl used separately and that the mixture II + Xl, the herbicidal action being the same.

Test results include at table 6 (see page 63 to 76)

Example 7

Drunk open ground, treated different plants to a growth height of 2 to 15 cm with the following active ingredients used separately and as mixtures in solution form tankmix emulsifying and dispersing:

I the 2.3 dihydro-3.3-to-diniéthyl and 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 and dibydro-to-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

17 the 3 a-INE thoxycarbonylaminophényl n - (3' - methylphenyl) sulfonylcarbamate

Y-quinic acid ethyl ester ii-ethyl-hence he-to-cyclohexylthiolcarbamic yi in the 3-cyclohexyl 5.6-trimethylene-uracil

yil the 1.2-to-dlméthyl and 3.5 to-diphénylpyrazolium-to-methylsulfate teh 26th 1' ethyl-substituted n-benzoyl-LF - (3.4-dichlorophenyl) - 2 a-aminopropionate IX 4 chloro-hexadiine and 2 a-yl 1 ester of n-3 a-ehlorophenylcarbamic

X is the methyl ester of the acid a-chloro-P-- (4-chlorophenyl) propionic acid

XIV and the 2.3 and 4ibydro-to-3.3-to-diiûéthyl and 2 a-méthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

Xv frames the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-ylméthylaminosulfonate

with respectively 0.5, 1.5 and 2 kg/Ba pp.a, the I + III-V-+, + + I-yi in nor, nor the I + + rearward Iy, the I + + III-IX., i + m + yii, the I + + in-Yin to, the I + III in the X +, n + m + y, the n + + ln-VI, II-m-rearward Iy + +, n + m + ix, the II + + in-Vll, the II-III-VIII + +, + + X-nor the II, m + y xiy +, + + m-xiy VI., + + in-xiy rearward Iy, xiy of m + + IX., xiy + + in-yii, + + yiiixiy of m, m + x + xiy, xy + m + y, x7 + m + yi, Y + + rearward Iy of m, the m + + XY-IX., the m + + XY-Vll, the m + + XY-yiii, x7 + + III-X with respectively 0, 5 + 0, 5 + 1, 5, 0, 5 + 1, 5 + 0, 5 and 1, 5 + 0, 5 + 0, 5 kg/ha to p * a *

At the end of 12 to 15 days, it is established that the mixtures have better compatibility with respect to crop plants that the active principle Xl, used separately and that the mixture II + Xl, the herbicidal action being the same.

The results of attempts to include at table 7 (page 77 to 82)

Example 8

In greenhouse, is treated different plants to a growth height of 2 to 18 cm with the following active ingredients used separately and as mixtures in the form of emulsion-to-dispersiontankmix:

I the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 dihydro-3_F. 3 dimethyl 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

IV 3 a-méthoxycarbonylaminophényl n '- (3' - methylphenyl) sulfonylcarbamate

V ethyl ester is n-ethyl-n-cyclohexylthiolcarbamic VI. the 3-cyclohexyl 5.6-trimethylene-uracil

VII is 1.2-dimethyl 3" 5 a-diphénylpyrazolium-to-methylsulfate VIII. 1 'éthyl-n-benzoyl-n - (3.4-dichlorophenyl) - 2 a-aminopropionate

IX 4 chloro-hexadiine and 2 a-y1-to-1 ester acid e 3 a-chlorophenylcarbamic

X is the methyl ester of the acid a-chloro-§- - (4-chlorophenyl) propionic acid

XIV and the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-yldiméthyl-to-aminosulfonate

Xv frames the 2.3 dihydro-3.3-dimethyl 2 a-méthoxybenzofurane-a 5 a-ylméthylaminosulfonat th

with respectively 1, 2, 4 kg/ha of pp.a.

+ + I-IX. of hi, I-VIII-IX. + +, + + X-I-IX., II-VII-IX. + +, + + II in the VIII and IX, the X + + II to IX., I-VIII of the X + +, + + the II-VIII to X, the I + III-V-+, + + I-III-VI compound, I-III-VI + +, + + III-I-IX., the I + + III-VII below, the I + II + VIII., the I + III-the X +, + + II-III-V., the II-III-VI + +, + + the II-III-IV, II-III-IX. + +, + + II-III-VII below, the II-III-VIII + +, + II-III in the X +, + + a V-XIV-III, III-VI compound-XIV + +, + + III-VI-XIV, xiy + + in-IX., + + Gn-XIV of m, the m-XIV + + NAV, + + X-ih-XIV, + + III-V-Xv frames, the III-VI + + Xv frames, + + III-VI Xv frames, + + III-IX. Xv frames, + + III-VII-Xv frames, + + III-VIII-Xv frames, + + X with Ill Xv frames respectively 1 + 1 + 2, 2 + 1 + 1,

1 + 2 + 1 kg/acre pp.a "

and for comparison with

Xi 2 chloro-4.6-diethylamino-a 1, 3, 5 triazine, 2 and 4 kg/ha of pp.a.

The II-III + + 1 + 1 + 2 kg/ha of XI with pp.a.

At the end of 12 to 16 days, it appears that the blends have improved compatibility with herbicides that the active principle Xl used separately and that the mixture II + + III-XII, the herbicidal action being the same.

related tests results include at table 8, (page

83 to 90)

Example 9

In open ground, treated different plants to a growth height of 2 to 12 cm with the following active ingredients used separately and in mixtures as émulsiondispersion:

I the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-ylméthylaminosulfonate

II to the 2.3 dihydro-3.3-dimethyl 2 a-éthoxybenzofurane-a 5 a-yldiméthylaminosulfonate

IV 3 a-ffléthoxyoarbonylaminophényl n - (3' Me¹ 1 hylphény1) butylcarbamate

V ethyl ester is n-ethyl-n-cyclohexylthiolcarbamic

VI. the 3-cyclohexyl 5.6-trimethylene-uracil

VII is 1.2-dimethyl-3.5-to-diphénylpyrazolium-to-methylsulfate VIII. 1 'éthyl-n-benzoyl-n - (3>4-dichlorophenyl) - 2 a-aminopropionate IX 4 chloro-hexadiine and 2 a-y1-to-1 ester of n-3 a-chlorophenylcarbamic

X is the methyl ester of the acid a-chloro-^ - (4-chlorophenyl) -

propionic

svec

V and VI respectively 0.5 /" 1, 2 kg/Group of pp.a,

The I, III, VI, VIII, VIII-, and IX, X with respectively 0.5, 1, 2 and 3 kg/ha to pp.a.

The I + + VI-VI, VII-I-VI as + +, + i + 7i-VIII, the I + + IV and IX, the I-VI + + X with respectively 0,5 + 0" 5 + 1 , 0, 5 + 1 + 0,5, 1 + 0,5 + 0,5 kg/ha. pp.a.

The X + + I-VI, II-VI 6.3 + +, + + IV to VII-II inhibitor, the II + + VI-VIII, II-IV of the X + +, + + I-VI and IX, the I + + IV to VII below, the I + 1 + 1 + 1 + VTII rearward Iy with respectively, 2 + 0,5 + 0, 5 , 0, 5 + 0,5 + 2, pp.a 0,5 + 2 + 0,5 kg/acre.

I + v + VIII, VIII-i + v +, i + v + ix, i + v + x, the II + + V-VI, II-V-VI as + +, + + II-V-VII below, the II-VI and IX + +, the II-VI the X + +, + + II-VI-VI, II-VI-VII-+ +, + + the II-VI-VIII, i + v + iv, i + v + vi, II-VIII-V-+ +, + + II-V-IX., the II + v + x with 0,5 + 0,5 + 1 respectively, 0,5 + 1 + 0,5, 1 + 0,5 + 0,5 kg/ha. pp.a,

I-VIII-NLV + +, + + I-VII-X-, II-VII-X-+ +, + II-VII-VIII with respectively 1 + 1 + 1 +, 2 + 0,5 + 0, 5 , 0, 5 + 2 + 0,5, pp.a 0,5 + 0,5 + 2 kg/acre.

and for comparison with

Xi 2 chloro-4.6-to-diéthyiamino-a 1, 3, 5 triazine with 2 and

3 kg/ha to the P, has.

The II XL + + 2 + 0,5 + 0>5 kg/ha to TV with a P, has.

At 12 to 15 days Pout, variables that the blends have enhanced compatibility with herbicides that the active principle Xl used separately and that the mixture Xl + + II-IV enzyme, the herbicidal action being the same.

test results include at table 9 (page 91 to 98)

Example 10

In-open ground, treated different plants to a growth height of 10 cm to 1 with the following active ingredients used separately and in mixtures as émulsiondispersion:

III in the 1 - phenyl-4-amino 5 a-chloropyridazone - (6)

The 3 - rearward Iy&éthoxycarbonylaminophényl n - (3'-methylphenyl) sulfonylcarbamate

Yi in the 3-cyclohexyl 5.6-trimethylene-uracil

VII is 1.2-dimethyl-3.5-to-diphénylpyrazolium-to-methylsulfate VIII to the 1-ethyl n-benzoyl-n-- (3.4-dichlorophenyl) - 2 a-aminopropionate

IX 4 chloro-hexadiine and 2 a-y1-to-1 ester acid mandate also 3-chlorophenyl carbamic

X is the methyl ester of the acid a-chloro-P-- (4-chlorophenyl) propionic acid

XVI as the 2.3 dihydro-3.3 -<iiméthyl-to-2 PR-uranium-a 5 a-yldiméthylaminosulfonateopoxybenzof

XVII to the 2.3 dihydro-3.3-dimethyl 2 a-isopropoxybenzofurane-a 5 a-yldiméthylaminosulfonat th

XIII the 2.3 dihydro-3.3-dimethyl 2 a-allyloxybenzofurane-a 5 a-ylméthylaminosulfonate

Form XIX the 2.3 dihydro-3.3-dimethyl 2 a-propargyloxybenzofurane-a 5 a-yl méthylaminosulfonate

with respectively 0.5, 1, 1.5 and 2 kg/ha of pp.a, + III-XIV, III-XVII to +, + III-XIII, lll + Form XIX, XIV + VI, VI + xvn, and RV xvm +, + VI Form XIX, + VI-XIV, IV + XVII properties, XIII-VI +, + Form XIX-VI, VII-XIV +, + XVII to the VIII, IX to XIII +, + X-Form XIX, with 0, 5 + 1, 5 respectively, 1, 5 + 0, 5 and 1 + 1 kg/ha in the P " has.

in-+ + VI-XIV, the m + + IX. as xM, nor xvin + + VI, III-XIII NLV + +, + + Yiii Ra of the m, the m + + Form XIX the X, XIV + + VI-VI, XVII to the X + VI +, + + IX to XIII-IV, VII-IV enzyme Form XIX + +, + + IV to XIII 0,5 + 1 + 0,5 VTII with respectively, and 1 + 0,5 + 0,5 pp.a 0,5 + 0,5 + 1 kg/acre.

At the end of 12 to 15 days, it is found that the mixtures show better herbicidal action that the active substances used separately, the compatibility with respect to crop plants being the same.

Test results are shown in Table 10 (page 99 to 104)

Example 11

In greenhouse, is filled earth clay pots are created and sandy and seeded seeds of various plants.

Then treating the earth so prepared with the following active ingredients used separately and as mixtures in the form of emulsion-dispersing:

III 1 phenyl 4-amino 5 a-chloropyridazone - (6)

V ethyl ester is n-ethyl-n-cyclohexylthiolcarbamic VI. the 3 a-cyclohe3yl and 5.6-trimethylene-uracil

XII as the 2.3 and dichlorallylester n, n diisopropylthiolcarbamic

XIII is the 2, 3, 3 a-trichlorallylester acid I, n diisopropylthiolcarbamic

XVI as the 2.3 dihydro-3.3-dimethyl 2 a-propoxybenzofurane-a 5 a-yldiméthylaminosulfonate

XVII to the 2.3 dihydro-3.3-dimethyl 2 a-isopropoxybenzofurane-a 5 a-yldiméthylaminosulfonate

XIII the 2.3 dihydro-3.3-to-diniéthyl and 2 a-allyloxybenzofurane-to-5 yl " methylaminosulfonat th

Form XIX the 2.3 dihydro-3.3-to-diniéthyl and 2 a-propargyloxybenzofurane-a 5 a-y1-me thylamino tallow onat th

The redundantable 2.3 dihydro-3.3-dimethyl 2 a-allyloxybenzofurane-a 5 a-yldiméthylaminosulfonate

Lll, a V, XII and XIII with respectively 0.5, 1, 1.5 and 2 kg/ha to pp.a.

IV, XIV, XVII properties, XIII, Form XIX and redundantable with respectively 0.5, 0.75, 1, 1.5 and 2 kg/ha to pp.a.

+ III-XIV, III-XVII to +, + III-XIII, lll + Form XIX, Ill redundantable +, + a V-XIV, XYII XII as +, + XIII XIII, x3x + XIII., redundantable XIII with respectively 0, 5 + 1, 5 +, 1, 5 + 0, 5 and 1 + 1 kg/acre pp.a.

the m + + willwill xra XII as, m + m + v, III-xvm as xM + +, + + Form XIX-III-VI, the m + + redundantable XIII, XIV + + XII as junk, Σ + 7 + ΠΠ 711, mils + + a V-VI, + + V with XII as redundantable 0,5 + 0,5 + 1 respectively, and 1 + 0,5 + 0,5 0,5 + 1 + 0,5 kg/ha. pp.a.

Vi + x7i, yi + x7ii, XIII TrV +, + TrV Form XIX, IV + redundantable with respectively 0,5 + 1, 1 + 0,5 and 0, 75 + 0, 75 kg/ha. pp.a.

After 5 to 4 weeks, it is found that the mixtures show better herbicidal action that the active substances used separately, the compatibility with respect to crop plants being the same.

test results include at table 11 (page 105 to 110)

TABLE 1

Table 1 (result)

1 (result)

THE I + + + I-II-III-IV + V.

1.5

0.5 0.5 1

0.5 1, 0.5

1, 0.5 0.5

THE I + III-XII AS + + + I-II-III-III-V-XIII IS + +

Table 1 (result)

TABLE 1 ()

0=without effect

100=total destruction

Table 1 (result)

1 - TABLE

1 (fine)

0 ≈ without effect

100 ≈ complete destruction

TABLE 2

the O>>95,100 100,100 95,100 100,100 100,100 12, 15 20, 40 75, 8î - F.

2 (result)

0=without effect

100 complete destruction

Table 2 (result)

Table 2 (result)

Table 2 (result)

Table 2 (result)

total

Table 2 (result)

Table 2 (result)

2 (fine)

0 ≈ without effect

100=total destruction

TABLE 3

Table 3 (following)

Table 5 (following)

TABLE 3

T XIIT Ill Xv frames + + + III-VI-Xv frames

THE I + + XT IS ITR

0.5 0.5 2

80

Vj1 ER

100,100 100,100 XL

100

100, 65 35,100 0.5 2, 2 0.5 2, 0, 5 0.5

0, 0

4

Table 4 (result)

0 ≈ without effect

100=total destruction

5

v_nthe O VBE1

total table 5 (following)

Table 5 (following)

VJI Œ10 5 (following)

0 the m without effect

100 complete destruction

Active Prinoine

kilograms/acre, [B.A..

THE II-VI +

0.5 1.5 1.5 0.5

Plantqoulture of T- The beta vulgaris extract

1 Planted IndésiraTalea the I Has Venn|ratua

aparineGaliua

Of Matricaria chamomilla

without effect

100 90, 95 95, 98 98,100 complete destruction

5 - Table (following) -

The V-XIV-XIV-XIV-VI + + + + +-XIV-XIV VIII-VIII and IX-XIV + 5 + III-X-Xv frames (fine)

ru table 6