SU576895A3 - Herbicide composition - Google Patents

Description

(54) HERBICIDE COMPOSITION

This invention relates to herbicidal compositions based on organic compounds, in part based on derivatives of diphenyl ether. Lime is a herbicidal composition in which 4-chloro-4 nitrodiphenyl ether is used as the active principle. However, it exhibits insufficient herbicidal activity. In order to find new herbicidal compositions and compositions with a higher herbicidal activity, a composition based on diphenyl ether derivatives of the formula I is proposed.

Z represents a nitro group, a halogen atom or cyanogroste,

the rest of the additive is an emulsifier, dispersant, solvent.

The recommended concentration of active nredated in the composition is 1-90 parts by weight, preferably 5-80 parts by weight.

The active ingredients of the present invention can be obtained by the following methods:

2 - Halo - 4 - trifluoromethyl diphenyl ether having the general formula I

15

where X means a halogen atom,

n is 0-3,

Y is hydrogen, a halogen atom, a lower alkyl group, Ci — Cj g alkoxy, lower alkoxy alkoxy, lower alkenyloxy, lower alkynyloxy, lower alkyl mercapto, amino, lower alkylamino, lower dialkylamino, acetylamino, allylamino, hydroxy or 12 dimethylamino / alkoxy 25

where XT p and Y have the meanings indicated, are reacted with a nitrating or halogenating agent in order to substitute the B 4 group for the nitro group or the halide group to form a compound.

4 - Cyanosubstituted compounds I are obtained by reduction of the corresponding nitro compound and to the amino compound, which are diaaeted and the resulting compound is subjected to reactions of Ca dumeier pi Guttermash; 3 - substituted 4 - nitro compounds) I obtain by the reaction of substitution of halogen in the presence of alkali between 3 halides of 4 nitro compounds of the corresponding C ,. alcohol, lower alkoxy alcohol, lower alkenyl alcohol, lower alkylene alcohol, and other substituents. The active ingredients obtained according to the described procedures are given below. 2-chloro-4-trifluoromethyl-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3-methoxy-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3-to-4-nitrodiphenyl ether 2-chloro-4- trifluoromethyl-3-and-propoxy-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3-isopropoxy-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3-n-butoxy-4-nitrodiphenyl ether 2,4- 2-chloro-4-trifluoromethyl-4-bromodiphenyl ester 2,4-di chloro-4-trifluoromethyl-3-methox diphenyl 2,4-dichloro-4-trifluoromethyl-3-ethoxydiphenyl ether 2 chloro-4-trifluoromethyl-diphenyl ether 2,4-dichloro-4-three ether Fluormetsh-1 - 3 - “- 2,4-dichloro-4-trifluoromethyl-3-n-2-chloro-4-trifluoromethyl-3-methoxy-4-diphenyl 2-chloro-4-trifluoromethyl-3-ethoxy-2-chloro-4-trifluoromethyl-3-methoxy-4-diphenyl 2-chlorophenyl ether -4-f p diphenyl ether 2-chloro-4-trifluoromethyl-3-methyl-4-nor trodiphenyl ether 2,3-dichloro-4-trifluoromethyl-4-nicro diphenyl ether 2,4-dichloro-4- 82,3,4-trichloro-4-trifluoromethyl-diphenyl zfir trifluoromethyl-3-methyl-diphenyl ether 92-chloro-4-trifluoromethyl-4-cyanodiphenyl ether 0 2-chloro-4-trifluoromethyl-3methyl-x-4-cyanodiphene1 12 -chloro-4-trifluoromethyl-3-to-propoxy-4-cyanodiphenyls 2 ether 2-chloro-4-trifluoromethyl-3-ethyl-4 nitrodiphenyl ether 32-chloro-4-trifluoromesh-1-3-17 e-butyl-4-nitrodiphenyl ether 42-bromo-4-trifluoromethyl-4-4-chloro-diphenyl 52-bromo-4-trifluoromethyl-3-methoxy-4-chloro-diphenyl ether 62-bromo-4-trifluoromethyl-3-ethoxy-4-chloro-diphenyl ester 72-bromo-4-trifluoromethane-1-4-shgrodiphenyl ether 82-bromo 4-trifluoromethyl-3-metsh1-Z-methyl-4-nitrodiphenyl ether 92-bromo-4-trifluoromethyl-3-methoxy-4-nI throdiphenyl ether 02-bromo-4-trifluoromethyl-3-ethoxy-4-nitrodiphenylsulfur 12 -bromo-4-trifluoromethyl-4-cyaniphenyl ether 322-fluoro-4-trifto Methyl-3-methyl-4-nitrodiphenyl ether 332-fluoro-4-trifluoromethyl-3-methoxy-4-nitrodiphenyl ether 2-iodo-4-trifluoromethyl-3-etoc s-434 -nithodiphenyl ether 352-iodo-4-trifluoromethyl -3-ethoxy-4 bromodiphenyl ether 362,6-dichloro-4-trifluoromethyl-4-nitrodiphenyl ether. 37. 2,6,4-trichloro-4-trifluoromethane1 Diphenyl ether

2,6-dihpor-4-trifluoromethyl-3-methyl-4-nitrodiphenyl ether

2,6,4-trichloro-4-trifluoromethyl-3-megoxydiphenyl ether

2,6-dichloro-4-trifluoromethyl-3-methoxy-4-bromodiphenyl ether

2,6-dichloro-fluorofluoromethyl-3-methoxy-4-nitrodiphenyl ether

2,6-dichloro-4-trifluoromethyl-3-ethoxy-4-bromodiphenyl ether

2,6-dichloro-4-trifluoromethyl-3-ethoxy-4- and 2-chloro-4-trifiOrmethyl-6-fluoro-4-nitro-2-chloro-4-trifluoromethyl-6-fluoro-3-trifluoromethyl 2-chloro-4-trifluoroment-1-3-amino-4-nit 2-chloro-4-trifluoromethyl-methyl 4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3-methylamino-4 nitrodiphenyl ether gQ 2-chloro-4-trifluoromegyl-3-ethylamino ester -4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl 1-3-n-propyl-gg g amino-4-nitrodiphenyl ester 2-chloro-4-trifluoromethyl-3-isopropylamio-4-nitrodiphenyl ether 2-chloro-4-chlorofluoromethyl - 3-dimethylamino-4-nitrodiphenyl ether 2-chloro-4-trifluoromethy L-3 -di-ethylamino-4-nitrodiphenyl ether 45 2-chloro-4-trifluoromethyl-3-diethid-73 amino-4-chlorodiphenyl ether 2-chloro-4-trifluoromethyl-3-di-n-pro 50 74 ylamino-4 2-chloro-4-trifluoromethyl-3-all-1-amino-4-nitro-diphenyl 2-chloro-4-trifluoromethyl-3-acetylamino-4-nitro-diphenyl 2-chloro-4-trifluoromethyl-3-Iopropylmercapto-4-nitro-diphenyl ether Ether 60

582-chloro-4-grifluoromethyl-3-sec-methyl merto-4-nitrodiphenyl ether

592-chloro-4-trifluoromethyl-3-methyl-1-ethoxy-4-shgrodiphenyl ether

602-chloro-4-trifluoromethyl-3-ethoxyegoxy-4-nitrodiphenyl ether

612-chloro-4-trifluoromethyl-3-allyloxy-4-nitrodaphenyl ether

622-chloro-4-trifluoromethyl-3- (2-propynyl)

hydroxy- 4-nitrodiphenyl ether

13

632-chloro-4-trifluoromethyl-3-hydroxy-4-nitrodiphenyl ether 64 65 66 67 68 70 71 72 75 76 77 2,6-dyslor-4-trifluoromethyl-3-ethimine-4-nitrodiphenyl ether 2,6-dichloro -4-trifluoromethyl-3-isopropylmercapto-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-3- (2-dimethylamino) ethoxy-4-nitrodiphenyl ether 2-xdor-4-trifluoromethyl-3-n-octyloxy-4 -nithodif 2,3,5,6,4-pentachlor-4-trifluoromethyl-3-label sulphate ester 2,6,4-trichloro-3,5-difluoro-4-trifluoromethyldiphenyl 2,6,4-trichloride sidiphenyl ether -3,5-difluoro-4-trifluoromethyl-3-methyldiphenyl ether 2,6,4-trichloro-3,5-difluoro-4-trifluoromethyl-3-labels with 2,4-dichloro-3,5,6-trifluoro-4-trifluoromethyldiphenyl ether 2,4-dichloro-3,5,6-trif tor-4-trifluoromethyl-3-methyldiphenyl ether 2,4-dichloro-3 diphenyl ether , 5,6-trifluoro-4-trifluoromethyl-3-methoxy-diphenyl ether 2,4-dichloro-3,5,6-trif-tor-4-neck tormethyl-3-ethoxydiphenyl ether 2,3,5,6-tetrafluoro-4 2,3,6,4-tetrachloro-4-tr 11-fluoro-methyldiphenyl ether 2,3,5,6-tetrachloro-4-trifluoromethyl-3-methyl-4-nitro-diphenyl ether 2,3,5,6-tetrachloro- 4-trifluoromethyl-Ztoksi-4-nitrodiphenesl ester 2,6-dichloro-3,5-dafluoro-4-trifluorometi-methoxy-4-nitrodiphenyl esters 2-chloro-3,5,6-trifluoro-4-trifluoromethyl 4-nitrodiphenyl 2-chloro-3,5,6-trif-tor-4-trifluoromethyl 3-metsh-4-nitro-diver 1 3-methyl ester 2-chloro-3,5 - trifluoro-4-trifluoromethyl-3 toxi-4-nitrodiphenyl ether 2-chloro-3,5,6-trifluoro-4-trifluoromethyl-3-ethoxy-4-nitrodiphenyl ether 2,3,5,6-tetrafluoro-4- 2,3,6-tetrafluorotrichloro-4-trifluoromethyl-4-nitrodiphenyl trifluormethyl-4trodiphenyl ether, 2,3,6-trichloro-4-trifluoromethyl-3-methyl-4-nitrodiphenyl ether 2,3,6-trichloro- F trifluoromethyl-3-labels of si-4-nitrodiffeshyl ester 2-chloro-4-trifluoromethyl-3, 4-difluorodiphenyl ether

PRI mme R 2. Each vat depth of 1/3000. And ipolshpot soil and supersaturated with water. Seeds of broadleaf weeds, such as Monochoria, Tootheup, and spike-leaved spike, Slenedr Spikerush, are placed in vats to a depth of about 5 mm, water is poured into each vat to a depth of 3 cm. After the weeds are sprayed, they are sprayed water sperm of each active ingredient. After 14 days, the surviving weeds are examined. The test results for 2 - chloro - 4 - trifluoromethyl - 4 - nitrodiphenyl ether are given in Table. one.

The degree of plant growth regulation is indicated by the following standards;

5 - complete suppression of plant growth.

4- excellent plant growth suppression.

3 - Clearly suppressed growth compared to untreated plants.

2 - weak suppression of plant growth.

1 is the same height as untreated plants.

PRI me R 3. Each 1/90 pot is filled with soil and the seeds of wheat, carrot, radish, tomato, cabbage, Chinese cabbage and edible chicken millet are sown in pots and covered with soil, which is covered with soil containing ordinary seeds. a weed, such as wild chicken millet, marsh wort (bog stitch - wort), grass, undulating bitter watercress, at a depth of 2 cm. Three days after sowing, the water dispersion of each ingredient is sprayed onto the soil. After 10 days, the growth state of each pacTeitHH is examined. The results are shown in Table. 2

The active ingredient used is 2 - chloro - 4 - trifluoromethyl - 4 -, nitrodiphenyl ether

Other active ingredients showed the same results. 2,6-dachloro-4-trifluoromethyl-3-bromo-4-n -trodiphenyl ether 2,6-dibromo-4-trifluoromethyl-3-methyl 4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl-- 3-n-methyllyloxy- 4-nitrodiphenyl ether 93 2-chloro-4-trifluoromethyl-3-n-pentyloxy-4-nitrodiphenyl ether 2-hl or-4-trifluoro letyl-3-and-hexyloxy-4-nitrodiphenyl ether 2-chloro-4-trifluoromethyl - 3-vortexyloxyI4-nitrodiphenyl ether 962-chloro-4-trifluoromethyl-3-n-heptyloxy-4-nitro-dipheshire ether Below are some examples in which most compounds were used. Example. Each crucible is 1/10000 oh full of goth with soil and mixed with water. Air-dried seeds of edible chicken millet are sown in a crucible and covered with soil. After the appearance of chicken millet on the surface of the earth, water is poured into each pot to a depth of 3 cm and then the water dispersion of the active ingredient is poured. After 14 days, each surviving plant is removed, dried and weighed. The results of grass survival from the treated and untreated seeds are given below. As the active ingredient, 2 chlorine 4 - trifluoromethyl - 4 - nitrodiphenyl ether is used. PRI me R 4. Each pot is filled with soil at 1/5000 and is sown: squeeze the food chicken millet and crush it with soil. When chicken millet exhausts to a three leaf state, I spray a certain amount of a 2-chloro-4 trifluoromethyl 4-nitrodiphenyl ether aqueous dispersion on its stems and leaves. 10 days after spraying, the growth condition of the millet is checked. The results are shown below. . The amount of active ingredient, g / a 10 5 The degree of growth control 5 5 PRI me R 5. In example J, but using the specified active ingredients. The results are shown in Table. 3. EXAMPLE 6 In Example 1, except that water is poured to a depth of 4 cm, when the plants have 2 leaves, and 18 days after this treatment, the test is performed. The results are shown in Table. 4. An example. In example 2 using the specified active ingredients. The results are shown in Table. 5 EXAMPLE 8. According to Example 3. But using the indicated active ingredients. The results are shown in Table. 6. PRI me R 9. According to example 4, but using the specified active ingredients. The results are shown in Table. 7. PRI mme. R 10. According to example 1, but using these active ingredients. The results are given in table. 8. The ingredients used are indicated by the numbers given above. Example 11. In example 6, but using the following active ingredients. The results are shown in Table. 9. Example 2. In example 2, but using the following active ingredients. The results are shown in Table. 10. Broadleaf weeds (Slenedr spikerush) are designated B, narrow-leaved grate S., Example 13. In example 6, but with the exception that rice seeds and air-dried edible chicken millet were sown when the plants Chicken millet have 1.5 leaves, pour water and spray the active ingredient. The results are shown in Table. 11. PRI me R 14. In Example 3, but with the use of the indicated active ingredients. The results are shown in Table. 12. PRI me R B. For example 3, IO using the specified ingredients. The results are shown in Table. 13. Example 16. In example 4, but using the following active ingredients. The results of P1 are listed in Table. 14. The amount of herbicides depends on the weather, the soil, the form of the agent produced, the time of year, the method of application and the weeds. Usually, 0.5-100, preferably 2.5-50 g / a, of the active ingredient is used. Composition I, (wt.h) 2-Chloro-4-trifluoromethyl-4-nitrodiphenyl ether5 Bentonite90 Sodium ligninsulfonate 5 The above components are mixed and granulated with water to form a herbicide (). Composition 2, (w / w) 2-Chloro-4-trifluoromethyl-4 nitrodiphenyl ether 20 2-Trifluoromethyl-4-chloro-4-nitrodiphenyl ether 0 Kaolin powder 55 Alkyl benzene sulfonate sodium 5 The above components are unevenly mixed to form a herbicide (we can only mix 1) Composition 3, (wt.h) 2-Chloro-4-trifluoromethyl-3-labels si-4-nitrodifferent ester 15 Polyoxyethylene stearate 20 Xylene 65 The above components are mixed to form a herbicide solution (emulsion). Composi 4, (wt.h) 2-Chloro-4-trifluoromethyl-3-ethoxy-4-nitrodiphenyl ether40 Kaolin powder55 Alkyl benzene sulfonate sodium 5 The above components are mixed non-uniformly to form a herbicide (wettable powder) Composide 5, (weight.h) 2- Chloro-4-trifluoromethyl-3-methyl-4-nitrodifesh1Lovy ester15 Polyoxyethylene stearate20

Marsh St. John's wort

Grass

Wavy Bitter Cress - Salad

Table 1

table 2

Active ingredient

2-Hlf-4-trifsfmethyl-. -3- labels si-4- nitrodifeshishovy ether

2-Chloro-4-trnfluorometal .3-ethoxy-4-nitrodiphenyl

2-Chloro-4-trifluoromesh-1-3-to-propoxy-4-n -trodiphenyl ester

2- Chloro-4-trifluoromethyl-3-isopronoxy-4-nitrodiphenyl ether

2- Chloro-4-trifluoromethyl-3-n-butoxy-4-nitrodiphenyl ether

2- Chloro-4-trifluoromethyl-3-methoxy-4-nitrodifferent 1 ester

2- Chloro-4- trifluoromethyl-3-ethoxy-4-n-nitrodiphenyl ether

2- Chloro-4-trifluoromethyl-3- "-nropoxy-4-nitrodiffeshoxy ester

2- Chloro-4- trifluormetsh J- 3 - "- butoxy-4-nitrodiphenyl ether

The degree of regulation of growth with the amount of the active ingredient, g / a

0000

0000

0000

0000

0000

T a b l and c a 4

. ABOUT

2- Chlorine- 4- trifluorTable 6

Table 8

One table) 8

Active ingredient

Experience

80) 2-Chloro-4-trifluoromethyl-3. methoxydiphenyl ether

8F 2,2-Dichloro-4-trifluoromethyl-dipheiyl ether

82) 2-Bromo-4.trnfluoromethyl-3ch epoxyethyphoxy ether

83) 2-Chloro-4-trnfluoromethyl-2-methyldifesh ether

84) 2.6-Dichloro-4-trifluoromethyl-diphenyl ether

hl

80-84 known active ingredients.

14 15 17 19 22 25 28 29 31 39 41 43 47 48 49 50 51 52 54 55 59 60 61 62

Continuation of table 8

Growth rate (%) with the number of active infusion, g / a

20

ten

85

82

94

97

92

Table 9

oh oh

7

about

sixteen

one

oh oh 16 oh oh oh oh oh oh

oh oh oh oh oh

20

five

oh oh oh oh

oh oh oh oh

34 2,4,6-TiHfxnop-3-methoxy-4-nitro phenyl ether88

jf. 35 2-Trifluorome1Il-4-chloro-3-methoxy-,

- 4- nitrodifeshitovy ether100

x) 34-35 - known active ingredients.

G should not table 9

97

100

W) a favor of the table W

ten

83

85

eleven

Table 11

1 table 12

33

34 G favor table 12

10 60

11 61

Table 13

Continuation of table 13 Table 14

Claims (1)

Invention Formula Gvrbitsida-composition, including the active active ingredient based on derivatives of dphenyl ether, as well as one million several additives - emulsifier, dispersing agent, solvent, which in order to increase the herbicidal activity, it contains forge .X ; o h Ha Gf favor table 14 where X is a halogen atom, n is 0-3, Y - means hydrogen, halogen atom, lower alkyl group, Ci-Ci g alkoxy, lower alkoxyalkoxy, lower alkenyloxy, lower alkynyloxy, lower alkyl mercapto, amino, lower alkylamino, lower dialkylacium, acetylamine, allylamino, hydroxy or (2-dimethylamino) groups, Z represents a nitro group, a halogen atom, a wi cyano group, moreover, the content of active active ingredient 1-90 weight. parts, preferably 5-80 weight.h.