JPS5842864B2 - N-(α,α-dialkylbenzyl)phenylacetamide derivatives and herbicides containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound, an N-(α·α-dialkylbenzyl)phenylacetamide derivative, and a herbicide containing the novel compound as an active ingredient.

Conventionally, various herbicides for paddy rice cultivation have been commercially available, but they have various drawbacks, such as harming paddy rice and only a few types of weeds that can be weeded.

At present, there are almost no practically effective weeds against Cyperaceae weeds, which are particularly difficult to control.

The present inventors first developed a herbicide with the general formula RCH2C0NHC(CHa)2C6H5 (wherein R is Indicates a phenyl group or a phenyl group substituted with 1 to 3 halogens.

A herbicide containing an N-(α·α-dimethylbenzyl)-acetamide derivative represented by (Japanese Unexamined Patent Publication No. 104240) was developed.

Furthermore, as a result of continuing extensive research on the N-benzylamide compound of phenylacetic acid, the present inventors found that α.
Based on α-dialkylbenzylamine bound to phenylacetic acid, we developed a series of new compounds by introducing specific substituents into the benzene nucleus of the phenylacetic acid moiety and the benzylamine moiety. It was discovered that it is an extremely useful herbicide, and the present invention was completed.

That is, the present invention is based on the general formula (wherein Xl and X2 represent a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, or a hydrogen atom, group or a hydrogen atom, R2 represents an alkyl group having 1 to 3 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an allyl group or a hydrogen atom, and R3 and R4 represent an alkyl group having 1 to 4 carbon atoms. , n represents 1-3.

However, this excludes the case where R1 and R2 are hydrogen atoms and R3 and R4 are methyl groups.

), and the N-(α・α-dialkylbenzyl:phenylacetamide derivative)
The present invention provides a herbicide containing a (α·α-dialkylbenzyl)phenylacetamide derivative as an active ingredient.

In the compound represented by the above general formula (I), Xl
As mentioned above, may be a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, or a hydrogen atom, but from the viewpoint of the herbicidal effect of the compound, a halogen atom, especially a chlorine atom, is the most preferred. Preferred is an alkyl group or an alkoxyl group.

Furthermore, the halogen atom has a small phytotoxicity to rice, and in particular, the bromine atom has a small phytotoxicity.6Furthermore, the alkyl group is preferably a methyl group, and the alkoxyl group is preferably a methoxyl group.

There is no particular restriction on the position of substitution of Xl on the benzene ring, but from the viewpoint of herbicidal effect, the ortho position is most preferred, followed by the meta position.

Next, R1 in the compound represented by general formula (I) may be an alkoxyl group having 1 to 3 carbon atoms, that is, a methoxyl group, an ethoxyl group, a propoxyl group, or a hydrogen atom, but an alkoxyl group is more suitable for rice cultivation. It is preferable because the chemical damage is small.

Furthermore, among alkoxyl groups, methoxyl groups are superior in terms of herbicidal effect.

Subsequently, R2 is an alkyl group having 1 to 3 carbon atoms, or an alkyl group having 2 to 3 carbon atoms.
6, an alkoxyalkyl group, an allyl group, or a hydrogen atom.

Examples of the alkyl group include a methyl group, an ethyl group, a flobyl group, and the methyl group is particularly excellent in terms of herbicidal effect.

Further, there are various alkoxyalkyl groups such as methoxymethyl group, ethoxymethyl group, and methoxyethyl group, but methoxymethyl group is particularly preferred.

In addition, from the viewpoint of the herbicidal effect of the compound, it is generally preferable that R2 be an alkyl group or hydrogen, followed by an alkoxyalkyl group.

However, the chemical damage to rice generally decreases as the number of carbon atoms in the substituent group increases.

R3, R4 are alkyl groups having 1 to 4 carbon atoms,
Specifically, methyl group, ethyl group, propyl group, etc. are preferable.

From the viewpoint of herbicidal effect, it is more preferable that one of R3 and R4 is a methyl group and the other is an ethyl group than when both are methyl groups.

Further, X2 may be any of a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, or a hydrogen atom, but from the viewpoint of herbicidal effect, a halogen atom is most preferred, followed by an alkyl group or a hydrogen atom. is preferred.

Further, this halogen atom has little phytotoxicity to rice, and chlorine atom and bromine atom are particularly preferable, and among them, chlorine atom is most preferable.

Further, as the alkyl group, a methyl group is preferable, and as the alkoxyl group, a methoxyl group is preferable.

There is no particular restriction on the position of substitution of X2 on the benzene ring, but from the viewpoint of herbicidal effect, the para position is most preferred, followed by the meta position.

Note that the number of X2 to be replaced is usually one, but it can also be two or three.

The novel N(α・α-
Dialkylbenzyl)-phenylacetamide derivatives can be prepared in various ways.

For example, thionyl chloride is added to phenylacetic acid or substituted phenylacetic acid and heated under reflux for 1 to 4 hours to obtain phenylacetic acid chloride or substituted phenylacetic acid chloride,
Next, these are reacted with α・α-dialkyl-substituted benzylamine and triethylamine in an ether solvent under heating under reflux for 0.5 to 3 hours to obtain the above N-(
[alpha].[alpha]-dialkylbenzyl)-phenylacetamide derivatives can be produced.

Another method is to dissolve phenylacetic acid or substituted phenylacetic acid in methylene chloride and add α·α-dialkyl-substituted benzylamine, triethylamine and N-methyl-2-chloropyridinium iosito to give 0.5-2.
It can be produced by heating under reflux for a period of time.

In order to isolate the target compound from the reaction mixture thus obtained, first a 5% aqueous hydrochloric acid solution is added, the solvent is distilled off under reduced pressure, and the precipitate is separated and dried over phosphorus pentoxide.

The target compound thus isolated is benzene, n-
It can be obtained as colorless to pale yellow needle-like crystals or prism crystals by base crystallization with hexane-methylene chloride or the like.

The compound of the present invention is a novel compound, suppresses the germination and growth of weeds, and has high selectivity, so it is suitable as a herbicide.

In other words, if the soil is treated before and after flooding in direct-seeded rice cultivation in dry fields, it will not harm the rice and will eliminate weeds of the Cyperaceae family, such as Cyperus cyperus, Cyperus japonica, Cyperus japonica, and Cyperus japonica.
Shows outstanding herbicidal effects against weeds such as grass weeds.

Furthermore, when used as a soil treatment agent in the early to mid-stage of transplanted rice cultivation, it can control the above-mentioned Cyperaceae and Poaceae weeds without harming the rice.

Furthermore, when used as a soil treatment agent in fields of broad-leaved crops, wheat, soybeans, etc., it can have a weeding effect without harming the crops, and is particularly effective against weeds of the Cyperaceae family, such as purple mulberry mask and annual cyperus. , there is almost no phytotoxicity to crops such as corn.

The herbicide of the present invention is used by mixing the compound as an active ingredient with a liquid carrier such as an organic solvent or a solid carrier such as fine mineral powder, and formulating it in the form of a wettable powder, emulsion, granule, granule, etc. be able to.

A surfactant may be added to impart emulsifying properties, dispersibility, spreading properties, etc. during formulation.

When the herbicide of the present invention is used in the form of a wettable powder, it usually contains 10 to 55% by weight of the above-mentioned compound of the present invention as an active ingredient, 40 to 88% by weight of a solid carrier, and 2 to 5% of a surfactant.
A composition may be prepared by blending the components in proportions of % by weight, and this may be used.

In addition, when used in the form of an emulsion, it is usually prepared by blending the compound of the present invention as an active ingredient in a ratio of 20 to 50% by weight, a solvent of 35 to 75% by weight, and a surfactant of 5 to 15% by weight. .

On the other hand, when used in the form of a powder, the compound of the present invention is usually used as an active ingredient in an amount of 1 to 15% by weight, and as a solid carrier, 80 to 97% by weight.
It may be prepared by blending the surfactant in a proportion of 2 to 5% by weight.

Furthermore, when used in the form of granules, it may be prepared by blending the compound of the present invention as an active ingredient in a proportion of 3 to 15% by weight, a solid carrier of 80 to 95% by weight, and a surfactant of 2 to 5% by weight. .

Here, fine mineral powder is used as the solid carrier, and examples of the fine mineral powder include oxides such as diatomite and slaked lime, phosphates such as apatite, sulfates such as ceracola, talc, and pyroferrite. Examples include silicates such as clay, kaolin, bentonite, acid clay, white carbon, quartz powder, and silica powder.

In addition, organic solvents are used as solvents, specifically aromatic hydrocarbons such as xylene, toluene, benzene, etc.
Chlorinated hydrocarbons such as chlorotoluene, trichloromethane, and trichlorethylene, alcohols such as cyclohexanol, amyl alcohol, and ethylene glycol, ketones such as isophorone, cyclohexanone, and cyclohexenyl-cyclohexanone, and ethers such as butyl cellosol, dimethyl ether, and methyl ethyl ether. , esters such as isopropyl acetate, benzyl acetate, methyl phthalate,
Amides such as dimethylformamide or mixtures thereof can be mentioned.

Further, as the surfactant, any of anionic, nonionic, cationic, and amphoteric ionic types (amino acids, betaine, etc.) can be used.

As described above, the N-(α・α-dialkylbenzyl)phenylacetamide derivatives of the present invention have a high herbicidal effect and are extremely useful as highly selective herbicides without phytotoxicity to crops, and are useful as other herbicides and growth regulators. It can be widely used by mixing with pesticides, fertilizers, etc., such as pesticides, insecticides, and fungicides.

Next, the present invention will be explained in more detail with reference to Synthesis Examples and Examples.

Synthesis Examples 1 to 27 5 mmol of a given phenylacetic acid derivative was dissolved in 3 methylene chloride.
0d, 5 mmol of α・α-dialkylbenzylamine or its derivative, 1 mol of triethylamine.
2 mmol and 6 mm of N-methyl-2-chloropyridinium iosite were added in this order, and after heating under reflux for 1 hour,
Cool to room temperature, then add 10 d of 5% aqueous hydrochloric acid solution,
The solvent was removed under reduced pressure.

The precipitated crystals were separated and dried with phosphorus pentoxide in a desiccator to obtain an N(α・α-dialkylbenzyl)phenylacetamide derivative, which was recrystallized from n-hexane-methylene chloride** tyrene. A purified product was obtained.

The results are shown in Table 1.

Furthermore, the analysis results of the obtained purified product are shown in Table 2.

In Table 2, the infrared absorption spectra were conducted using the KBr tablet method, and the proton nuclear magnetic resonance spectra were conducted using the CBr tablet method.
The experiment was conducted using DC13 as a solvent and TMS as an internal standard.

Example (1) Preparation of herbicide 97 parts by weight of talc (trade name Nidichrite) as a carrier, 1.5 parts by weight of an alkylaryl sulfonate (trade name: Neoperex, manufactured by Kao Atlas ■) as a surfactant, and 1.5 parts by weight of nonionic and anionic surfactants (trade name: Solbol 800A, manufactured by Toho Kagaku Kogyo ■) were uniformly ground and mixed to obtain a carrier for a wettable powder.

90 parts by weight of this hydrating agent carrier and N obtained in the above synthesis example.
A herbicidal wettable powder was obtained by uniformly pulverizing and mixing 10 parts by weight of a -(α·α-dialkylbenzyl)phenylacetamide derivative.

(2) Biological test results (flooded soil treatment test) Fill paddy soil in a 1/15500 are porcelain pot.
After uniformly sowing the seeds of Japanese wildflower, firefly, and Japanese cyperus on the surface layer, and transplanting the tubers of Japanese cyperus and flooding to a depth of 2 crfL, two-leaf stage paddy rice seedlings (variety: Ni Nihonbare) were planted.
I have ported this book.

When the weeds germinated, a predetermined amount of the diluted herbicide obtained in (1) above was uniformly dropped onto the water surface to treat the weeds, and then the pots were left in a greenhouse and watered at appropriate times.

Table 3 shows the results of investigating the herbicidal effect and phytotoxicity of paddy rice 20 days after the chemical solution treatment.

In Table 3, the dosage is shown by the amount of active ingredient, and the paddy rice damage and herbicidal effect were measured in the air-dried form and expressed as follows.

Ratio of paddy rice damage vs. untreated area ± 9 +〃9 ++〃8 +++ 〃6 100% 5-99% 0-94% 0-89% 0-79% Herbicidal effect O vs. untreated area 1 〃 100% 61 ~99% 2 to heat treatment area ratio 21~60% 3 〃 11~20% 4 〃 6~10% 4.5 // 1~5%5 〃
0% (Field soil treatment test) A 1/7800 are porcelain pot with a hole in the bottom was filled with field soil up to the 7th minute, seeds of wheat and soybeans and tubers of purple sloth were planted, and 1crfL of soil was covered.

Further, seeds of crabgrass, sypera, and one-year-old cyperus were mixed with the topsoil, and a predetermined amount of a diluted solution of the herbicide manufactured by CA in the above example (7J1) was uniformly sprinkled on the soil surface.
The plants were left in a greenhouse and watered from time to time.

Table 4 shows the results of investigating the herbicidal effect and chemical damage to wheat and soybeans 30 days after the chemical solution treatment.

Note that the display in Table 4 was carried out in the same manner as the display in Table 3.

(Stem and leaf treatment test) A 1/7800 are porcelain pot with a hole in the bottom was filled with field soil up to the 7th minute, and soybean, radish, and corn seeds and tubers of germinated purple leaf lily were prepared, 1 crfL.
Covered with soil.

When the first leaves of soybeans, the second true leaves of radish, 2 to 3 leaves of corn, and 3 to 4 leaves of Japanese radish were left in a greenhouse and watered at appropriate times, the method of (1) in the above example was applied. A predetermined amount of the prepared diluted herbicide at a liquid volume of 2001/10 are was uniformly sprayed onto the foliage of the plants.

The plants were left as they were in the greenhouse, and watering of the stems and leaves was avoided for 3 days after treatment, and thereafter, water was sprinkled from the stems and leaves at appropriate times.

Table 5 shows the results of investigating the herbicidal effect and chemical damage to soybeans, radish, and corn 30 days after the chemical solution treatment.

The display in Table 5 was carried out in the same manner as the display in Table 3.

Claims (1)

[Scope of Claims] 1 Formula (wherein Xl and X2 represent a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxyl group having 1 to 3 carbon atoms, or a hydrogen atom, and R1 R2 represents an alkyl group having 1 to 3 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an allyl group or a hydrogen atom, and R3 and R4 represent an alkyl group having 1 to 4 carbon atoms. represents a group, and n represents 1 or 2. However, R1 and R2 are hydrogen atoms, and R3 and R4
except when is a methyl group and when X2 is a substituent bonded to the ortho position. ) N-(α・α-dialkylbenzyl)phenylacetamide derivative represented by 2. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein Xl is substituted at the ortho or meta position. 3. The N(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein X2 is substituted at the para position and/or meta position. 4 N-(α・α-dialkylbenzyl) according to claim 1, wherein Xl and X2 are halogen atoms
Phenylacetamide derivative. 5 N-(α・α-dialkylbenzyl) according to claim 1, wherein X2 is a chlorine atom substituted at the para position
Phenylacetamide derivative. 6. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein Xl is a chlorine atom substituted at the ortho position, and X2 is a chlorine atom substituted at the para position. 7 A patent claim in which Xl is a chlorine atom substituted at the ortho position, X2 is a chlorine atom substituted at the para position, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group The N (α·α-dialkylbenzyl)phenylacetamide derivative according to item 1. 8 A patent claim in which Xl is a chlorine atom substituted at the ortho position, X2 is a chlorine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. The range of N-(α・α-
Dialkylbenzyl)phenylacetamide derivatives. 9 A patent claim in which Xl is a chlorine atom substituted at the ortho position, X2 is a chlorine atom substituted at the para position, R1 is a hydrogen atom, R2 is an allyl group, and R3 and R4 are methyl groups. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to item 1. 10X1 is a bromine atom substituted at the ortho position, and X2
Claim 1, in which is a chlorine atom substituted at the para position
N-(α·α-dialkylbenzyl)phenylacetamide derivatives described in 1. 11X1 is a bromine atom substituted at the ortho position, and X2
is a chlorine atom substituted at the para position, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. Dialkylbenzyl)phenylacetamide derivatives. Claim 1, wherein 12X1 is a hydrogen atom, X2 is a chlorine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. N-(α・αdialkylbenzyl)
Phenylacetamide derivative. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein 13X2 is a chlorine atom substituted at the meta and para positions. 14 Xl is a chlorine atom substituted at the ortho position, and X2
is a chlorine atom substituted at the meta and para positions, and R1
is a methoxyl group, R2 is a hydrogen atom, and R
3. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein R4 is a methyl group. N-(α・α-dialkylbenzyl) according to claim 1, wherein 15X2 is a bromine atom substituted at the para position
Phenylacetamide derivative. 16X1 is a chlorine atom substituted at the ortho position, and X2
is a bromine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups,
α-Dialkylbenzyl)phenylacetamine derivatives. N-(α・α-dialkylbenzyl) according to claim 1, wherein 17X2 is a chlorine atom substituted at the meta position
Phenylacetamide derivative. 18 Xl is a chlorine atom substituted at the ortho position, and X2
is a chlorine atom substituted at the meta position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups.
-Dialkylbenzyl)phenylacetamide derivative. 19. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein X2 is a methyl group substituted at the meta position. 20X1 is a chlorine atom substituted at the ortho position, X2 is a methyl group substituted at the meta position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. N-(α・α-
Dialkylbenzyl)phenylacetamide derivatives. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein 21X2 is a methyl group substituted at the para position. 22X1 is a chlorine atom substituted at the ortho position, and X2
is a methyl group substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups,
-Dialkylbenzyl)phenylacetamide derivative. 23 Xl is a chlorine atom substituted at the ortho position, and X2
is a methoxyl group substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3, R4
is a methyl group, N-(α
・α-Dialkylbenzyl)phenylacetamide derivative. N- according to claim 1, wherein 24X1 is a chlorine atom substituted at the ortho position, and X2 is a hydrogen atom
(α・α-dialkylbenzyl)phenylacetamide derivative. 25 Xl is a chlorine atom substituted at the ortho position, and X2
, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group, the N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1. 26 Xl is a chlorine atom substituted at the ortho position, and X2
The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein R1 and R2 are hydrogen atoms, and R3 and R4 are ethyl groups. 27 Xl is a chlorine atom substituted at the ortho position, and X2
is a hydrogen atom, R1 is a methoxy group, R2 is a hydrogen atom, and R3 and R4 are methyl groups, the N-(α・α dialkylbenzyl)phenylacetamide derivative according to claim 1 . 28X1 is a chlorine atom substituted at the ortho position, and X2
is a hydrogen atom, R1 is a methoxyl group, R2 is a hydrogen atom, R3 is an ethyl group, and R4 is a methyl group, N-(α・α
-Dialkylbenzyl)phenylacetamide derivative. Claim 1, wherein X1 is a chlorine atom substituted at the ortho position, X2 is a hydrogen atom, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are ethyl groups. N-(α・α-dialkylbenzyl)phenylacetamide derivative. Claim 1, wherein 30X1 is a chlorine atom substituted at the ortho position, X2 is a hydrogen atom, R1 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups. N(α·α-dialkylbenzyl)phenylacetamide derivatives as described. N- according to claim 1, wherein 31X1 is a bromine atom substituted at the ortho position, and X2 is a hydrogen atom
(α・α-dialkylbenzyl)phenylacetamide derivative. 32X1 is a bromine atom substituted at the ortho position, and X2
, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group, the N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1. 33X1 is a bromine atom substituted at the ortho position, X2,
The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein R1 and R2 are hydrogen atoms, R3 is a propyl group, and R4 is a methyl group. 34X1 is a bromine atom substituted at the ortho position, and X2
, R1 is a hydrogen atom, and R2, R3, and R4 are methyl groups, the N(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1. 35X1 is a bromine atom substituted at the ortho position, X2,
Claim 1, wherein R1 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups.
N-(α·α-dialkylbenzyl)phenylacetamide derivatives described in 1. 36. The N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1, wherein Xl is a methyl group substituted at the ortho position and X2 is a hydrogen atom. 37X1 is a methyl group substituted at the ortho position, and X2
, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group, the N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1. 38X1 is a methyl group substituted at the ortho position, and X2
, R1 is a hydrogen atom, and R2, R3, and R4 are methyl groups, N-(α・α-
Dialkylbenzyl)phenylacetamide derivatives. 39X1 is a methyl group substituted at the ortho position, and X2
, R7 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups, the N-(α·α-dialkylbenzyl)phenylacetamide derivative according to claim 1.匍 General formula (wherein, Xl and X2 represent a halogeno atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, or a hydrogen atom, and R1 is an alkoxyl group having 1 to 3 carbon atoms or hydrogen R2 represents an alkyl group having 1 to 3 carbon atoms, an alkoxyalkyl group having 2 to 6 carbon atoms, an allyl group or a hydrogen atom, R3 and R4 represent an alkyl group having 1 to 4 carbon atoms, and n is 1 or 2. However, R1 and R2 are hydrogen atoms, and R3 and R4
except when is a methyl group and when X2 is a substituent bonded to the ortho position. A herbicide containing an N-(α·α-dialkylbenzyl)phenylacetamide derivative represented by ) as an active ingredient. 41. The herbicide according to claim 40, wherein 41X0 is substituted at the ortho or meta position. 41. The herbicide according to claim 40, wherein 42X2 is substituted at the para and/or meta position. 43. The herbicide according to claim 40, wherein Xl and X2 are halogen atoms. 41. The herbicide according to claim 40, wherein 44X2 is a chlorine atom substituted at the para position. 45X1 is a chlorine atom substituted at the ortho position, and X2
Claim 4, in which is a chlorine atom substituted at the para position
The herbicide described in item 0. 46X1 is a chlorine atom substituted at the ortho position, X2 is a chlorine atom substituted at the para position, Ro and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. The herbicide according to scope 40. 47X1 is a chlorine atom substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein is a chlorine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. 48X1 is a chlorine atom substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein is a chlorine atom substituted at the para position, R1 is a hydrogen atom, R2 is an allyl group, and R3 and R4 are methyl groups. Claim 40, wherein X1 is a bromine atom substituted at the ortho position, and X2 is a chlorine atom substituted at the para position.
Herbicides listed in section. 50X1 is a bromine atom substituted at the ortho position, X2 is a chlorine atom substituted at the para position, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. The herbicide according to scope 40. Claim 40, wherein X1 is a hydrogen atom, X2 is a chlorine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. herbicide. 41. The herbicide according to claim 40, wherein 52X2 is a chlorine atom substituted at the meta and para positions. 53X1 is a chlorine atom substituted at the ortho position, and X2
is a chlorine atom substituted at the meta and para positions, and R1
is a methoxyl group, R2 is a hydrogen atom, and R
3. The herbicide according to claim 40, wherein R4 is a methyl group. The herbicide according to claim 40, wherein 54X2 is a bromine atom substituted at the para position. 55X1 is a chlorine atom substituted at the ortho position, and X2
The herbicide according to claim 40, wherein is a bromine atom substituted at the para position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. 56 The herbicide according to claim 40, wherein X2 is a chlorine atom substituted at the meta position. 57X1 is a chlorine atom substituted at the ortho position, X2 is a chlorine atom substituted at the meta position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. The herbicide according to scope 40. 58 The herbicide according to claim 40, wherein X2 is a methyl group substituted at the meta position. 59X1 is a chlorine atom substituted at the ortho position, X2 is a methyl group substituted at the meta position, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. The herbicide according to scope 40. 41. The herbicide according to claim 40, wherein 60X2 is a methyl group substituted at the para position. 61X1 is a chlorine atom substituted at the ortho position, and X2
The herbicide according to claim 40, wherein is a methyl group substituted at the para position, R□ is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. 62X1 is a chlorine atom substituted at the ortho position, and X2
is a methoxyl group substituted at the para position, R□ is a methoxyl group, R2 is a hydrogen atom, and R3, R4
The herbicide according to claim 40, wherein is a methyl group. 63X1 is a chlorine atom substituted at the ortho position, and
41. The herbicide according to claim 40, wherein 2 is a hydrogen atom. 64 Xl is a chlorine atom substituted at the ortho position, and X2
, R□, and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. 65 Xo is a chlorine atom substituted at the ortho position, and X2
The herbicide according to claim 40, wherein is a hydrogen atom, R1 and R2 are hydrogen atoms, and R3 and R4 are ethyl groups. Claim 40, wherein 66X1 is a chlorine atom substituted at the ortho position, X2 is a hydrogen atom, R1 is a methoxy group, R2 is a hydrogen atom, and R3 and R4 are methyl groups. herbicide. 67X1 is a chlorine atom substituted at the ortho position, and X2
The herbicide according to claim 40, wherein R1 is a hydrogen atom, R1 is a methoxyl group, R2 is a hydrogen atom, R3 is an ethyl group, and R4 is a methyl group. 68X1 is a chlorine atom substituted at the ortho position, and X2
The herbicide according to claim 40, wherein R1 is a hydrogen atom, R1 is a methoxyl group, R2 is a hydrogen atom, and R3 and R4 are ethyl groups. 69 X□ is a chlorine atom substituted at the ortho position, and
41. The herbicide according to claim 40, wherein 2 is a hydrogen atom, R1 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups. 70. The herbicide according to claim 40, wherein Xl is a bromine atom substituted at the ortho position, and X2 is a hydrogen atom. 71 Xl is a bromine atom substituted at the ortho position, and X2
, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. 72X1 is a bromine atom substituted at the ortho position, X2,
41. The herbicide according to claim 40, wherein R1 and R2 are hydrogen atoms, R3 is a propyl group, and R4 is a methyl group. 73X1 is a bromine atom substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein R1 is a hydrogen atom, and R3 and R4 are methyl groups. 74X1 is a bromine atom substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein R1 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups. 75. The herbicide according to claim 40, wherein Xl is a methyl group substituted at the ortho position, and X2 is a hydrogen atom. 76X1 is a methyl group substituted at the ortho position, and X2
, R1 and R2 are hydrogen atoms, R3 is an ethyl group, and R4 is a methyl group. 77X1 is a methyl group substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein R1 is a hydrogen atom, and R2, R3, and R4 are methyl groups. 78X1 is a methyl group substituted at the ortho position, and X2
41. The herbicide according to claim 40, wherein R1 is a hydrogen atom, R2 is a methoxymethyl group, and R3 and R4 are methyl groups.