JPS58192808A - Herbicide - Google Patents

Abstract

PURPOSE:A herbicide showing extremely excellent cooperative action and synergistic action, exhibiting properly selective herbicidal action, having improved prolonged effect, obtained by blending a substituted phenylsulfonylurea derivative with a diphenyl ether derivative. CONSTITUTION:A herbicide comprising a substituted phenylsulfonylurea derivative [e.g., N-2-biphenylylsulfonyl, N'-(4-methoxy-6-methyl-pyrimidine-2-yl)urea, etc.] shown by the formula I [X is O, or single bond; Y is H or Cl; R is group shown by the formula II or formula III (R<1> and R<2> are methyl or methoxy)] and a diphenyl ether derivative (e.g., 2,4-dichlorophenyl 3-methoxycarbonyl-4-nitrophenyl ether, etc.) shown by the formula IV(X is Cl or CF3; Y is H or Cl; Z is H, alkoxy, etc.) as active ingredients. EFFECT:Having improved safety, showing a wide herbicidal spectrum and durability with improved effect.

Description

[Detailed description of the invention] It is something.

More specifically, (wherein, X is an oxygen atom or a single bond, Y is a hydrogen atom or a chloro atom, and R'' and R3 are a methyl group or a methoxy group) 5 substituted phenylsulfonylurea derivatives (In the formula, x is a chlorine atom or a trifluoromethyl group, Y is a hydrogen atom or a chlorine atom, and 2 is a hydrogen atom, a lower alkoxy group, a tetrahydro7ran-3-yloxy group, or a lower alkyl dicarbonyl group) The present invention relates to a herbicide mixture that is characterized by being blended with the diphenyl ether derivatives shown below to produce a synergistic effect that is unexpectedly strong when applied alone, and capable of killing many kinds of problem weeds with a low application rate.

Currently, many herbicides have been put into practical use as herbicides for paddy fields, and are widely used as single agents or mixtures.

However, there are many types of paddy weeds, and although there are many herbicides that are effective against annual weeds, there are very few herbicides that are effective against perennial weeds. As a result, the number of perennial weeds has increased, and there is a strong need for their control.

Polycrystalline weeds generally grow vigorously and have a long outbreak period, making it difficult to completely control them. Therefore, herbicides are desired to have a broad spectrum of herbicidal properties that can kill many types of weeds.

In addition, in recent years, mechanization and earlier transplantation of rice cultivation have become increasingly popular, providing a more suitable environment for weeds to grow than ever before, and it is expected that repeated herbicide applications will result in complete weed control. tend not to be able to do so.

For this reason, the same or different herbicides are used several times, but the repeated use of such herbicides not only requires a great deal of labor, but also causes problems such as chemical damage to paddy rice and soil residue due to large amounts of application. It raises undesirable issues.

Regarding substituted phenylsulfonylurea derivatives, as a result of repeated testing and research in order to find a new wi derivative having superior herbicidal activity, the applicant first discovered a novel substituted phenylsulfonylurea represented by the general formula (I). It was discovered that the derivative has excellent selective herbicidal activity (Patent Application Sho 36-/Ko I
Ij90) 0 □In order to improve these interlayer points of conventional herbicides, the inventors have developed a herbicide that can completely control all weeds by multiple spraying and is highly safe for paddy rice. However, as a result of repeated research in order to develop a safe herbicide with extremely low toxicity to humans and animals, we have now found a herbicide of the above general formula (I) that exhibits herbicidal activity.
An excellent herbicide that improves these problems can be obtained by blending a novel substituted phenylsulfonylurea derivative represented by the formula (n) with a diphenyl ether derivative represented by the general formula (n), which is known as a herbicide. He learned this and completed the present invention.

The herbicide of the present invention exhibits extremely pronounced synergistic and synergistic effects by mixing the herbicides as in the present invention, even at concentrations where each of the constituent single agents would not be sufficiently effective on its own. It exhibits accurate selective weed control, and shows a remarkable control effect even against weeds in advanced leaf stages (weeds corresponding to the leaf stage such as Novie / - / J leaf stage) due to its synergistic effect. At the same time, it is possible to achieve satisfactory selective control even for grass species for which nest-based chemicals have not been shown to be sufficiently effective. Weeds such as the following were confirmed. The herbicide of the present invention was also found to have even better properties in terms of residual effectiveness.

Therefore, an object of the present invention is to provide a novel mixture, particularly a herbicide, and the present invention has been completed based on the above discovery.

Preferred examples of the substituted phenylsulfonylurea derivative represented by the general formula (I) used in the herbicide 5 of the present invention include the following compounds.

Compound No. (1) N-cobiphenidylsulfol, N'-(lI-methoxy-6-methyl-pyrimidin-2-yl)urea, m
p/99~-02℃ Compound number (co) N-2-biphenylylsulfonyl, N'-1,4-dimethyl-pyrimidin-λ-yl)urea, mp203~2
01"C Compound No. (3) N-cophenoxyphenylsulfonyl, N'-(DermeFx-6-methyl-pyrimidin-2-yl)urea, mp/9≦~CoOO℃Compound No. (≠) N -2-<2-chlorophenoxy, cy)phenylsulfonyl, N'-(Hiro-methoxy-t-methyl-pyrimidine-
2-yl) urea, mp2/6~λ20℃ Compound number C
J”) N-J-phenoxyphenylsulfonyl, N'-(cap6
-cymethyl-pyrimidine-coyl) urea, mp17
tNllrO°C Compound No. (6) N-2-biphenylylsulfonyl, N'-(lI-methoxy-6-methyl-/, 3-sheet triazin-yl)
Urrea, rmp/90 N/9! °C compound number (7) N-2-biphenylylsulfonyl, N'-1,4-dimethoxy-/, 3.3-) riazine-coyl 5-urea, mp/7 j N/ 10''C compound number @ (,
r) N-2-phenoxyphenylsulfonyl, N'-(dermethoxy≦-methyl-/, JJ-)riazin-2-yl)urea, mp/I! f~/90°C Compound No. (9) N-2-phenoxyphenylsulfonyl, N'-(dau-6-simethoxy/J,j-triazin-2-yl)urea, mp/t O-/6j''C compound No. CIO> N-2-C2°-chlorophenoxy) phenylsulfonyl, N'-($s4-dimethoxy/, 3J-triacyn-choyl) urea, mpco O7~20 II"C Also, Hontaimei weeding The general formula (
Preferred examples of the diphenyl ether derivative II) include the following compounds.

However, it is not limited to these.

Formula;
nox, bifenox) formula; Chlorophenyl ether (ONF), represented by λ-rijirou! -) Rifluoro p-methylphenyldernitro-J-(tetrahydro7lan-3-yloxy)phenyl ether, Nicro p-dertrifluoro9methylphenyl 3-ethoxy-tI-di)a phenyl ether of the formula: or : 1,1I-diclerophenyl p-R phenyl ether (NIP).

The herbicide of the present invention has low toxicity to hemorrhagic animals and good selectivity to cultivated plants, that is, it does not cause any chemical damage to cultivated plants at normal concentrations, so it can be used as a herbicide for weed control. It can be conveniently used for The word weed here means, in its broadest sense, any plant that grows where it is not desirable.

The herbicide of the present invention exhibits excellent selective control efficacy and excellent durability of efficacy, particularly when used as a pre-emergence soil treatment agent for paddy field weeds or as a foliage and soil treatment agent.

It also exhibits excellent herbicidal activity, a wide herbicidal spectrum, and excellent persistence of efficacy.

For example, as a paddy field weed, Botanical name Latin name: Dicotyledonous plant Rotala 1ndica Ko@hn
eAze Llnd@rnla pr
ocumbana Ph1lcox Phyllanthus L
udwlgla prostrata Roxb.

Potamog@ton distlnc
tusA, B@nnet Mizo Chickweed Elatln@triandra 8eh
monocot plant Ichlnochloa
crus-gall P, B@auv.

Monoehoria vag
lnalls Presl.

Matsubai 1ileocharIs acIcular
ls Room, 5t8ehult.

ri4guwai-11eochar1s kuroguwa
j Ohwl Tamagayatsuri 0FI) erua dl
fformls L.

Oyp@rus 5erot1nus
Rottb.

8agittaria p
ygma@a Mlq.

Omodaka 8aglttarla trlfolIa
L.

Allima canalicula
tummu, Br, 5tBouch≦ Firefly 5clrpus junco1d@s Ro
xb, 5ubsp.

hotarul(Ohwl)T, Keyama Himehotarui 8clrDua lln@olatus Fr
aneh at8av.

8-circus *tu
barculatum O, Kuntg＊5ubsp
, n1pponlcus T, Koyama Koukyagara 8c1rpus planleulmls F
Herbicidal activity has been observed in plants such as r, 8chmldt, etc., and it has the characteristic that it has no harmful effect on paddy rice.

When using the herbicide of the present invention, it can be diluted directly with water, or it can be used in agricultural chemical production or by using an agricultural chemical auxiliary.
It can be used in various formulation forms by methods commonly practiced in the field. In actual use, these various preparations may be used directly or
It can be used by diluting it with salt or water to a desired concentration.

The pesticide adjuvants referred to here include, for example, diluents (solvents, fillers, carriers), surfactants (solubilizers, emulsifiers, dispersants,
(wetting agents), stabilizers, and fixing agents.

Solvents include water: organic solvent; hydrocarbons [e.g., naphtha, petroleum fractions (paraffin wax, kerosene, light oil, middle oil, heavy oil), benzene, toluene) xylenes], halogenated hydrocarbons (e.g., chloro methylene, tetracyclic (tJ element,
) IJ Rolztyrene, ethylene chloride)', ethylene diA, chlorobenzene, chloroform], alcohols 11. Methyl alcohol, ethyl alcohol, propyl alcohol, ethylene glycol], esters [e.g., ethyl ether, ethylene oxide, dioxane], alcohol ethers (e.g., ethylene glycol, monomethyl ether), tons [
Examples include acetone, isophorone], esters [e.g. ethyl acetate, amyl acetate], amides [e.g. dimethylformamide, dimethyl acedoylamide], sulfoxides [e.g. dimethyl sulfoxide]. Inorganic materials such as slaked lime, magnesium lime, gypsum, calcium carbonate, sand stone, etc. can be used as carriers.
Burley i1 Pumice, calcite, diatomaceous earth, amorphous nitric oxide, alumina, zeolite, clay minerals (e.g. pyrophyllite, talc, montmorillonite, beidellite, verculite, kaolinite, mica): vegetable organic substances e.g.; flour , starch, modified starch, sugar, glucose, crushed plant stems: synthetic resins, e.g.; phenolic resins,
Examples of surfactants include anionic surfactants; alkyl sulfate esters [e.g. sodium sulfate], aryl sulfones [e.g. alkylaryl sulfone WI] #1, sodium alkylnaphthalene sulfonate), succinates, Borie 6-ethylene glycol alkylaryl ether sulfate salts: cation (
Cation) Surfactants; Alkylamines [e.g., laurylamine, stearyl trimethyl ammonium chloride, alkyldimethylpencil 7 ammonium chloride], polyoxyethylene alkyl amines
: Nonionic surfactant; polyoxyethylene glycol ethers [e.g., polyoxyethylene alkylaryl ether and its condensates], polyoxyethylene glycol esters [e.g., polyoxyethylene fatty acid ester], polyhydric alfur Examples include esters (for example, polyoxyethylene sorbitan monolaurate): amphoteric surfactants, and the like.

Other stabilizers, fixing agents [e.g., agricultural soap, casein lime, sodium alginate, polyvinyl alcohol (
(PV), vinyl acetate adhesives, and acrylic adhesives].

The mixed active compound of the present invention can be manufactured into various formulations by methods generally practiced in the agricultural chemical manufacturing field. Examples of the form of the preparation include emulsion tomato oil, wettable powder, suspension, powder, granules, powder, granules, tablets, and cabbage tablets.

The herbicide of the present invention contains the mixed active ingredients in an amount of 007 to 700.
It can be contained in an amount of 1 to 93% by weight, preferably 1 to 93% by weight.

In actual use, the various formulations and spray preparations described above (r@ady-to-us@-pr@para
The mixed active compound content in tlon) is generally 0.0
A suitable range is from / to 9j% by weight, preferably from O,OS to 60% by weight.

The content of these mixed active ingredients can be appropriately changed depending on the form of the preparation, the method of application, purpose, timing, location, and weed growth status.

The herbicide of the present invention may further contain other agricultural chemicals, such as insecticides, fungicides, nematicides, antiviral agents, herbicides, if necessary.
Plant growth regulators, [e.g., organophosphate compounds, carbamate compounds, dithio (or thiol) carbamate compounds, organochlorine compounds, dinitro compounds, organosulfur or metal compounds, antibiotics, substituted diphenyl ethers compound, urea-based compound, triazine-based compound] or/and fertilizer, etc. can also be made to coexist.

1. Various formulations or spray preparations containing the mixed active ingredients of the invention (r@ady-to-use-pr@p
aration) are the application methods commonly used in the agricultural chemical manufacturing field, such as liquid spraying (spray spraying), etc.
), dusting, granulation, water surface application]: Can be carried out by soil application [for example, soil mixing], etc.

The application amount per unit area is for each active ingredient,
The substituted phenylsulfonylurea derivative of the general formula (I) and the diphenyl ether derivative of the general formula (rl) are mixed at a mixing ratio of 0-1 parts by weight, preferably 1 part by weight of /:10-1 ha. Approximately 0.2 to 72-1, preferably 0.2 to 6 to 6 O1j are used per mixed active compound. However, in special cases it is possible to exceed or fall below these ranges.
And sometimes it's even necessary.

The present invention contains as active ingredients a compound selected from the ta-phenylsophonylurea derivatives represented by the general formula (I) and a diphenyl ether derivative represented by the general formula (1), and a diluent (a solvent and a /or fillers and/or carriers) and/or surfactants,
Furthermore, if necessary, herbicidal compositions containing, for example, stabilizers and fixing agents are provided. ◇ Furthermore, the present invention provides methods for applying the mixed active compounds of the present invention alone or in the presence of diluents (solvents and A method for controlling weeds is provided in which the above herbicidal composition is mixed with a filler and/or a carrier) and/or a surfactant and, if necessary, a stabilizer and a fixing agent.

Next, the content of the present invention will be specifically explained with reference to Examples.
The present invention should not be limited to this only.

Example 1 (granules) 1 part of compound No. (3), 10 parts of the compound of formula (0), 29 parts of bentonite (montmorillonite), dried at 0-10°C as 10-110 gourd granules using a barrel granulator. and make granules. Sprinkle this on weeds and/or their growing areas.

Example 2 (granules) Compound number (7) 1 part, compound of formula (D) 3 parts, bentonite (montmorillonite) 35 parts, talc (talc) 5 parts
7 parts of lignin sulfonate and 2 parts of lignin sulfonate, 2 parts of water was added and kneaded well, and the mixture was made into 10-I
The IO mesh is dried in the form of granules at ao-so°C to form granules. Sprinkle this on weeds and/or their growing areas.

Example 3 (granules) 9 parts of clay mineral grains having a particle size distribution of 0.2 to 0.2 were placed in a rotary mixer and dissolved in an organic solvent under rotation. 2 parts of compound number Cl0), formula ( After spraying 2 parts of the compound of E), and drying at <40-j O''C to make granules, the granules are sprinkled on weeds and/or their growing areas.

Example II (granules) 7 parts of the compound of formula (A) and compound number (j)/,
! 2 parts of water was added to a mixture of 1 part, bentonite (montmorillonite > 3 parts, talc (talc) !, !, 3 parts, lignin sulfonate, 2 parts, kneaded well, and extrusion granulated. Depending on the preference, it is made into granules of 10-tIO mesh and dried at yo-so°C to make granules.The amount of mixed active ingredient is 2.3!t per hectare.
When the grains were sprinkled on paddy fields in which wild grasses were growing around the /-/J leaf stage, the synergistic effect resulted in very good control of paddy field weeds.

Example j (hydrating powder) Compound No. (3) 9 parts, compound of formula (D) 30 parts, mixture of powdered diatomaceous earth and powdered clay </'-3> 36 parts, sodium alkylbenzenesulfonate part, alkyl Three parts of sodium naphthalene sulfonate formalin condensate are powdered and mixed to obtain a wettable powder. , dilute this with water,
Apply dropwise to weeds and/or their growing areas.

Example 6 (emulsion) Compound number (7) / lr part, compound 10 of formula (E)
1 part of xylene, 7 parts of polyoxyethylene alkyl 722yl ether, and 7 parts of calcium alkylbenzenesulfonate were mixed and stirred to prepare an emulsion. This is diluted with water and dripped onto weeds and/or their growing areas.

The unexpected superiority and remarkable efficacy of the mixed active compounds according to the invention can be seen from the following test results when used against various paddy weeds.

Test example / Preparation of test compound for control test by application to paddy field weeds in drought sewage: Using a granulator, by a normal granulation method, diameter o, sw
It was granulated into rod-shaped particles with a length of 1 to 3 cm.

Composition ratio (total 700 parts) Each mono-active compound /~9 parts Polyoxyethylene alkyl 7 ether The increase or decrease is adjusted by increasing or decreasing the amount of talc.) Test method: The test field was plowed to a depth of 20 NJJ■ using a tractor according to the usual rice cultivation method. Immediately after plowing, the field was flooded with water from an irrigation canal to a depth of 100 to 300 yen, and the first puddling was performed. After the first puddling l~2'EI,
The area was further flooded with water to a depth of about 1 cm and the final plowing was performed. Two days after final plowing, the water depth in the field was adjusted to 2 to 3 cm, and seedlings C were grown in special seedling boxes using a power rice transplanter.
/3-day seedling leaf age λ~ko, j leaves, plant height /j-/7C■) 1
Three to J plants were transplanted per plant. Immediately after transplantation, using a hard plastic sheet, 20I11″ (2m x /
10 to 20 tubers of the test weeds per wI were inoculated at a depth of 2 to 3 cm below the ground surface.

Thereafter, the water depth in the field was maintained at 3 to jes+ for a long period of time. Seven days after transplanting paddy rice, the compound prepared as above was applied in water. After a week of chemical application, control according to the criteria below.
We investigated the effects.

The evaluation of the effect is the weed killing rate for the 101 untreated area when compared to the untreated area. ioo s9:
90% or more and less than 100%:
to% or more but less than 90%7;
70% or more, less than 10 arcg: to% or more 7
Less than 0% S: Weed killing rate for untreated area 30% or more ≦less than 0% Il: lI
o% or more less than SO%3: #
30% or more, less than 30% 2:
20% or more, less than 30%/:
10% or more, less than 20% 0:
Evaluation of chemical damage to paddy rice less than 10%
"O" indicates no chemical damage.

The test results are shown in Table 1.

(Left below) The above test results show the effects of some representative examples of the active ingredients of the herbicide of the present invention, and similar tests have shown that other compounds have the same extremely excellent synergistic selectivity. Shows weeding effect.

The present invention, which has been explained in detail in the detailed description of the invention, can be specifically summarized as follows.

(1) From a substituted phenylsulfonylurea derivative represented by the general formula: (wherein, The selected compound and (wherein, A herbicide characterized by containing a diphenyl ether derivative represented by the following as an active ingredient.

(2) III-11 The substituted phenylsulfonylurea derivative of formula m and the diphenyl ether derivative of the general formula (1) are mixed in /120-43 parts by weight, preferably /
glO-2! / parts by weight of the herbicide according to item 1 above.

(8) The herbicide according to the above items 1 and 2, which contains the active ingredient in an amount of 00Ol to 9J weight range, preferably 0,OS to 60 weight range.

(4) A compound selected from the substituted phenylsulfonylurea derivatives of the general formula (I) described in I, and a compound selected from the substituted phenylsulfonylurea derivatives of the general formula (It
) A method for controlling weeds, which comprises applying an effective amount of a mixed active compound with a diphenyl ether derivative to weeds and/or their growing areas.

(5) The method for controlling weeds according to the above paragraph, wherein the weeds are paddy field weeds.

(6) The method for controlling weeds according to the above item 1, wherein the application rate of the mixed active compound is 0.2 to 9/2/1 ha, preferably O,SN≦~.

(7) Apply the substituted phenylsulfonylurea derivative represented by the general formula (I) and the diphenyl ether derivative represented by the general formula (II) to weeds and/or their growing areas alone or with a diluent (solvent and/or filler). and/
The method for controlling weeds according to item D above, wherein the herbicide is mixed with a carrier) and/or a surfactant, and if necessary, a stabilizer and a fixing agent.

Agent's name: Kawahara 1) - Ho Procedural amendment , Showa Sza year month/y1st Mr. Kazuo Wakasugi, Commissioner of the Patent Office l Incident display Special Akira! ;7-703113 2. Name of the invention herbicide 3. Person who makes corrections Relationship to the incident Patent applicant 4th generation manager Postal code 105 5. Date of amendment order Voluntary 6 Number of inventions increased by amendment '7. Subject of amendment Specification Contents of the 8 divine corrections As shown in the attached sheet □ 9 List of attached documents 65-

Claims (1)

[Claims] General formula: (wherein, X is an oxygen atom or a single bond, Y is a hydrogen atom or a chloro atom, and R1 and R3 are a methyl group or a methoxy group). Phenylsulfonylurea l1al
1 and the general formula: (wherein, A herbicide characterized by containing a diphenyl ether derivative represented by the following as an active ingredient.