DK141642B - Herbicide product. - Google Patents

Description

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The invention relates to novel herbicidal products having a surprisingly favorable herbicidal effect. The product according to the invention consists of a mixture of herbicidal past disorders, which mixture is more effective than the individual components.

A herbicidal product according to the invention is characterized in that it contains (a) 5-95 parts by weight of at least Sn compound. Offer the general formula: Q NH-O-R1, xc. "-

CT3 I

Wherein R is ethyl or propyl, R is allyl, and X is hydrogen or methoxycarbonyl or a sodium salt of the compound defined above, and (b) 95-5 parts of the herbicidal compound 3-methoxycarbonyl = aminophenyl-N - (3'-methylphenyl) carbamate.

15 The herbicidal material is selected taking into account the cultivated plant and the undesirable weeds in this area. The mixture of herbicides needed to control certain weed combinations that exist frequently provides a material that is not only toxic to the harmful weeds, but also to the cultivated plants.

Products of the present invention are mixtures of herbicides which have complementary effects and will therefore control a greater number of weed species, but do so by using lower concentrations than necessary when using the individual herbicidal compounds individually.

141642 2

The compound of the above formula (X) is particularly effective in controlling grass weeds.

It is believed that said compound of the above formula (I) has the following three chemical formulas due to tautomerism: 0 NH-O-R2 OH N-O-R2 rV'1 - rV "1" Hy * ·. "R-M ··

CH3 X ^ o ^ CH3 X

ID 1 ^ H-O-Ε2 (V) / Ψν ^ - LX0 ch3 x (VI) where X is hydrogen or a methoxycarbonyl group.

The compounds of formula (I) can be prepared in accordance with the following equation: OH o O NH-O-R2 jV "- - rV" 'HT · O' '. TYY10

3 [(VIII) CH3 I

Λ X

1 2 wherein R, R and X have the previously defined meanings.

When the above formula (VII) represents 5,5-dimethyl-2-acyl-3-hydroxy-2-cyclohexen-1-one, the above starting compound may be prepared according to the following equation: COOCH, NaOCH,

(CHO) 9C = CHCOCH2 + | IN

^ COOCH, in CEL · OB J

3 3 CH, 0 3 COOCHj O O Ψ o CDOfe in which has the meaning previously defined.

It is also believed that the starting compound of formula (VII) has three chemical formulas similar to formula (I) due to tautcanism.

The sodium salts are prepared by treating a compound of formula (I) above with a sodium hydroxide in aqueous solution or an organic solvent such as acetone, methanol, ethanol or dimethylformamide. The salts are isolated by filtration or by evaporation of the resulting solution.

Some of the compounds (a) can form hydrate in the following ways - 0 NH-O-R2 0 NH-O-R2 y ^ yC-R1 Jk ^ C-R1 JI + «2 ° -> I Γ 'H2 ° CH37 \ Ao '3 ^ 0 CH3X CH3 l (I) (IX) 1 2 wherein R, R and X have the meanings previously defined.

U1642 4

Some typical compounds of formula (I) which can be used in combination in the material of the invention are listed in Table 1.

Table 1, Compound No. _ Chemical Name_ Physical Constant 50 2- [1- (allyloxyamino) propyl = idene] -5,5-dimethylcyclohexane-n ^ 1,5119 1.3-dione 83 2- [1- (allyloxyamino) -butyl = idene] -5,5-dimethylcyclohexanine 1,5089 1,3-dione 90 2- [1- (allyloxyamino) -butyl = 24 idene] -4-methoxycarbonyl-5.5-n dimethylcyclohexane-1,3-dione 131 sodium salt of 2- [1- (allyl =

oxyamino) -propylidene-4-meth-175-178 ° C

oxycarbonyl-5,5-dxmethylcycloalkyl, hexane-1,3-dione 1 * '148 Sodium salt of 2- [1- (allyl = oxyamino) -butylidene] -4-meth = 9 ° oxycarbonyl-5, 5-dimethylcyclo = t.

hexane-1,3-dione ^ aeK *> xSmp. = melting point nQ = refractive index deck. = decomposition.

The compounds which may be included in a product according to the invention are hereinafter indicated by the number of the compound in Table 1.

As previously mentioned, it has been found that the mixture of a compound of formula (I) and the known herbicidal compound phenmedipham can have a synergistic herbicidal effect in addition to a cumulatively increased effect of each of the selected herbicidal functions.

In the following, the time practice of the invention is described in more detail.

The Carbamate Herbicide Included in the Product According to this invention, the name of the name is Trivial Name Phenyl) Carbamate Pbeneedipbam Herb 1 Sugar Beet, Herbicide's Effect on 10 Herbs

D6u XT '* ^ nnftrtft ui ^ S! 3! / 2lC! IJuB6f ρίΓΤΧιΤίΚΐΓ 2> 3 »^ ΒΑ ^ ρβ ^ CJpORisTTCBBtjJBHIBl J36 ^ ntIøHKBKXB

however, of a compound of formula (1) and carbamartic phenmedlphant is not only capable of extirpating both grass weed and broadleaf unknown tin door use but does not even exhibit two toxicities to the crops.

Using the invention in practice, mixtures of from 5 to 95% by weight of each component can be used, but towards 30-70% of each the best results are obtained.

The mixed product according to the invention can be fed directly to the soil as a pre-emergence treatment or to the plant foliage late post-emergence treatment or it can be mixed thoroughly with the soil and can be applied to the soil or plant foliage in quantities of more than 10 g of active ingredients. 1000 m, preferably above 25 g per meter. 1000 m.

The process according to the invention comprises the use of a liquid or solid product, containing two or more of the compounds of formula (I) and said well-known herbicide scan active ingredients.

141642 6

The active ingredient of the invention can be prepared by mixing with suitable carriers in a form commonly used in agricultural chemicals such as moist powder, emulsified concentrate, powder, granular product, water soluble powder and aerosol. As solid supports, bentonite, diatomaceous earth, apatite, plaster, talc, pyrophyllite, vermiculite, clay and other are used. As liquid carriers, water, kerosene, mineral oil, petroleum, solution benzene, benzene, xylene, cyclohexane, cyclohexanone, dimethylformamide, alcohol, acetone 10 and others are used. Sometimes surfactant is added to obtain a homogeneous and stable product.

The product of the invention can also be used in admixture with other chemicals used for agricultural and horticultural purposes. Such chemicals may be, but are not necessarily, such chemicals commonly used as plant nutrients, fertilizers, insecticides, acaricides, fungicides, herbicides and nematodicides.

The concentrations of the active ingredients in the herbicidal product of the invention may vary according to the type of preparation and they are used e.g. in amounts from 5-80 wt%, preferably 10-60 wt% in wettable powder, 5-70 wt%, preferably 20-60 wt% in emulsifiable concentrates and 0.5-30 wt%, preferably 1-10 wt in powdering agents.

Thus, a moist powder or an emulsifiable concentrate made therefor is diluted with water to a certain concentration and is thus used as a liquid suspension or liquid emulsion for the treatment of soil or plant leaves.

30 A powdering agent is further used directly for soil or foliar treatment.

The herbicidal products of the present invention U1642 7 are illustrated by the following examples.

Example 1.

Emulsifiable concentrate Weight portions 5 Compound 83 20

Phenmedipham 20

Xylene 35

Dimethylformamide 15

Polyoxyethylene phenyl ether 10 10 These are mixed and dissolved. Thus, an emulsifiable concentrate containing 40% of the active ingredient is obtained. For practical use, it is diluted to a certain concentration with water and then sprayed as an emulsion.

Example 2.

15 Moist Powder Weight Parts

Compound 90 20

Phenmedipham 20

White carbon 20 20 Diatomaceous earth 35

Alkyl sulfate 5

Example 3

Moist Powder Weight Parts 25 Compound 148 30

Phenmedipham 30

White carbon 10

Diatomaceous earth 22

Alkylsulfate · 8 8

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Experiment 1.

Leaf Treatment (Postergens)

Seeds of large finger axes and white flour goose feet were planted in a pot and covered with a bit of soil. The pots were readily placed in a greenhouse.

When the plants reached the fourth leaf stage, an aqueous emulsion was prepared by diluting an emulsifiable concentrate with water to a specific concentration sprayed on the leaves of the plants.

At 3 weeks after spraying, the fresh weight of the weed plants was determined above ground and the result is given in Table 2.

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Experiment 2

Post-emergence treatment by field testing

A field trial was conducted in mid-summer in Oiso-machi, Kanagawa Prefecture, Japan.

Two weeks after plowing, an experimental area was divided into 1 x 2 m pieces and aqueous emulsions of compounds prepared by diluting similar products as previously described were sprayed onto weeds in an amount of 100 1/1000 m2.

10 The weeds that grew in the experimental area consisted of both annual grasses and broadleaf weeds. The most important grass weed was the Digitaria adcendence Henr. (large finger axis) and Setaria viridis Beauv. (green fox tail). The most important broadleaf weeds were Chenopodium album L. (white flour goose foot), 15 Portulaca oleracea L. (regular portulak) and Galinsoga parviflora Cav. (Short beam).

Growth stages for weeds at the time of treatment were as follows:

Digitaria adscendens Henr. and Setaria viridis Beauv .: four-leaf leaf stage,

Portulaca oleracea L. and Galinsoga parviflora Cav .: two-leaf stage,

Chenopodium album L.: tree leaf stage.

25 Three weeks after treatment, the effect of the compounds on the weed growth was ascertained and assessed using a scale of 0-10. The 0-10 scale is defined as follows: 11 141642 O: no effect 1-3: the plant slightly damaged 4-6: the plant moderately damaged 7-9: the plant severely damaged 5 10: all plants discontinued.

The results are shown in Table 3

Table 3.

Tested compound Amount of grass- Broad (g / 1000 m2) weed leaf ______ weeds

Compound No. 90 100 10 0 50 8 0 '__25__5__0

Compound No.148 100 10 0 50 8 0 __25__5__0

Single phenmedipham 100 5 9 ___50__1 6

Compound No. 90 25 g g

Bian + phenmedipham 50 compound Compound no.148 25 99 + phenmedipham 50

The synergistic effect is shown in Table 3. Compounds Nos. 90 and 148 have no herbicidal action against broadleaf weeds when applied in an amount of 25-100 g / o 1000 m. Therefore, the synergism can be seen when comparing the herbicidal effect of phenmedipham alone at an applied amount of 50 g / 1000 m with the herbicidal effect of the mixture.

t The following results prove e.g. synergistic effect of the mixture: 12 14) 642 compound tested Amount of broadleaf weeds _ (g / 1000 m2) _

Phenmedipham £ 50

Compound No. 90 25 + - phenmedipham 50 8 ^

Compound No. 148 25 + phenmedipham 50 9_

The synergistic effect of the mixture is also shown in the following Table 4. Since Compounds Nos. 50, 83, 90, and 148 have no herbicidal action against white flour goose feet, the synergistic effect can be seen when comparing the herbicidal effect against the white flour goose foot of phenmedipham alone with the herbicidal effect towards the goose foot of the mixture at the same amount of application with respect to phenmedipham.

1Q Attempt i

Yellow raven tail (Alopecurus aequalis Sobol var. Amurensis Ohui) as grass weed and white flour goose foot (Chenopohium album L.) as broadleaf weeds were sown and grown in a pot (400 2 cm surface area) in a greenhouse. As the weeds grew to the 3-5 leaf stage, an aqueous emulsion, prepared by diluting an emulsifiable concentrate with water to a specific concentration, was sprayed onto the weeds in an amount equal to a water volume of 100 l. 10,000 m. Three weeks after treatment, the weeds were cut to measure the 20 fresh weight of the above ground plant parts.

The results are set forth in the following Table 4, in which the fresh weight of the weeds indicates numbers as relative value in comparison with untreated plant.

13 141642

Table 4.

Into Fresh weight of weeds (%) __ amount _ Yellow shrimp Compound (g / 1000 in) vehicular goose feet Total 25 83.2 103.1 94.8 50 51.8 100.3 80.0

No. 50 75 1.0 102.8 63.9 100 0 101.7 59.0 150 0 99.4 57.6 25 6571 108.0 9070 50 39.9 110.0 81.1

No. 83 75 0.5 104.7 60.9 100 0 101.0 58.6 150 0 99.9 57.8 25 51.0 105.6 82.7 50 23.3 108.3 72.6

No. 90 75 0 101.0 58.6 100 0 99.5 57.7 150 0 98.8 57.3 25 55.5 110.0 87.1 50 24.8 104.3 70.9

No. 148 75 0 102.0 59.2 100 0 102.0 59.2 150 0 99.7 57.8 25 5470 81.7 86.9 50 86.7 33.9 56.1

Phenmedipham 75 59.6 15.0 33.7 100 55.5 3.7 25.4 150 34.4 0 14.5 25 + 75 31.5 7.4 17.5

No. 50 + 50 + 50 15.6 17.1 16.5 phenmedipham 75 + 25 0 33.7 19.6 __75 + 75__0__2 / 2__1 / 3_ 25 + 75 9.6 Ϊ79 7.5

No. 83 + 50 + 50 0 13.0 7.5 phenmedipham 75 + 25 0 25.9 15.0 _, 75 + 75__0__Oj / 7__0 ^ 4_ 25 + 75 7.1 6.3 6.6

No. 90 + 50 + 50 0 11.8 6.8 phenmedipham 75 + 25 0 17.6 10.2 75 + 75 _0___0__Q_ 25 + 75 6.9 6.6 6.7

No. 148 + 50 + 50 0 12.3 7.1 phenmedipham 75 + 25 0 19.9 11.6 __75 + 75__g__g__g_

Untreated 100 100 100 _ (43.6) * (60.2) "(103.8) * () *: Fresh weight expressed by number of grams.