JPH02178265A - Pyridyloxy aliphatic carboxylic acid derivative, herbicide containing the derivative as main component and weeding method - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [X and Y are H, CF3 or halogen provided that at least one of X and Y is CF3; Z is =CH-or =N-; R<11> is H or 1-5C alkyl: R<12> is -OR<13> (R<13>=R<11>) or group of formula II (R<14> and R<15> are R<11> and bonded together to form a ring); A and B are O or S and positioned at m-position with each other; D is N positioned at o- or p-position relative to A and B and is not o-position relative to both A and B] or its salt when R<13> is H. EXAMPLE:The compound of formula II. USE:An active component of a herbicide. It gives a nonselective herbicide or selective herbicide against broad-leaved weeds effective at a low rate of application and exhibiting broad herbicidal spectrum by varying the group R<11>. The herbicide develops quick action in 2-3 days after scattering. PREPARATION:The compound of formula I can be produced e.g. by reacting a compound of formula III with a compound of formula IV in the presence of KOH and reacting the resultant compound of formula V with a compound of formula VI.

Description

DETAILED DESCRIPTION OF THE INVENTION a. Field of Industrial Application The present invention relates to a novel pyridyloxy aliphatic carboxylic acid derivative and a herbicide containing the compound as an active ingredient.

b. Prior Art In recent years, a large number of herbicidally active compounds have been studied, and some have been put into practical use, contributing to labor savings and improved production in agriculture. Among these are so-called selective herbicides that have relatively little impact on practical crops and control noxious weeds, as well as those that control undergrowth of fruit trees.

Non-selective herbicides are known that are used for purposes such as weed control in non-agricultural land. However, as described below, there is still room for improvement in the conventionally known herbicidal active compounds, and the emergence of new drugs is desired.

Among the above-mentioned known selective herbicidal active compounds, there is a type of herbicide that selectively kills broad-leaved weeds, such as 2゜4-dichlorophenoxyacetic acid, but this also includes narrow-leaved weeds. F, such as NatLlre, is known to have very weak activity or no activity at all against narrow-leaved plants.

155, p. 498 (1945)]. On the other hand, based on these compounds, compounds in which aromatic groups such as chloro- or trifluoromethyl-substituted phenoxy groups or chloro- or trifluoromethyl-substituted pyridyloxy groups are introduced selectively kill narrow-leaved plants. It is also known that the compound has the activity of [see, for example, JP-A-51-44531 and JP-A-52-125626].

Furthermore, when the aromatic group of the above-mentioned chloro- or trifluoromethyl-substituted phenoxyphenoxypropionic acids is replaced with, for example, a nitro-substituted pyridyl group, it has the activity of selectively killing broad-leaved weeds [for example, JP-A-59
-89864].

As explained above, the activity of phenoxyaliphatic carboxylic acid-based herbicidal compounds, especially the effect on plants, depends on the types and combinations of aromatic groups, aliphatic groups, and carboxyl groups in the skeleton of the compound. It is understood that this will vary significantly.

On the other hand, various compounds are known to have activity as non-selective herbicides, and representative examples include bipyridyl compounds and phosphorus-containing compounds [
For example, Japanese Patent Application Laid-Open No. 47-39538.

JP-A-52-139727, JP-A-54-67028
See issue].

Although bipyridyl compounds exhibit a herbicidal effect quickly, they are difficult to control perennial weeds, and their strong toxicity has recently become a problem. Furthermore, although the above-mentioned phosphorus-containing compounds have relatively low toxicity and a relatively wide herbicidal spectrum, they require an extremely long period of time to exhibit their herbicidal effects.

C9 Purpose of the Invention Therefore, the present inventors have developed a selective and non-selective herbicide that exhibits a broader herbicidal spectrum, has low animal toxicity and fish toxicity, has low soil persistence, and exhibits herbicidal activity rapidly. The present invention was achieved as a result of intensive research aimed at providing a herbicide that expresses the herbicide.

d0 invention, that is, the present invention is a novel pyridyloxy aliphatic carboxylic acid derivative represented by the following general formula (I) or R13
This is achieved by a herbicide containing a salt thereof (compound A) when is a hydrogen atom as the main active ingredient.

The present invention will be explained in detail below.

The pyridyloxy aliphatic carboxylic acid derivative (compound A) of the present invention is represented by the following general formula (I).

Here, X and Y are the same or different, and are hydrogen atoms, halogen atoms such as fluorine, chlorine, or bromine, or 10F
I, and either X or Y must be -CFx. X
It is necessary for Y to be one of these atoms or groups in order to achieve the object of the present invention, and the absence of these atoms or groups significantly reduces herbicidal activity. In the above formula (I), X is preferably -CF3, and Y is preferably a halogen atom.

Z represents =CH- or =N-, and =CH- is preferably used.

A and B are the same or different oxygen atoms or sulfur atoms, and are in meta positions with respect to each other. Also,
Preferably, A and B are oxygen atoms.

D is a nitrogen atom, which is in the ortho or para position to A and B, and never in the ortho position to both A and B.

Further, although the position of D varies depending on R11, it is preferably para to A and ortho to B.

R11 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. Here, the alkyl group having 1 to 5 carbon atoms is linear, but may necessarily be branched, such as methyl, ethyl,
n-propyl, +30-propyl, n-butyl, 5e
C-butyl, 15O-butyl.

t-butyl, n-pentyl, etc., and a hydrogen atom.

A methyl group, an ethyl group, etc. are preferred.

Ethyl, propyl, butyl and the like are preferred.

Furthermore, in the present invention, a so-called functional salt of the pyridyloxy aliphatic carboxylic acid represented by the general formula (I>) that retains the herbicidal effect may be used.As the functional salt, an alkali metal salt of the carboxylic acid may be used. .

alkaline earth metal salts, ammonium salts and the like, where R13 is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and examples thereof include the same ones as represented by R11 above. Further, R14 and R15 are the same or different and are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and furthermore, these may cooperate with each other to form a ring. Representative examples of the alkyl group having 1 to 5 carbon atoms include those similar to R11 above, but R14 and R15
A typical example of a ring formed by the two jointly forming a ring is −
R14-R15 is +CHz+4. (-Ct-12+s, etc. are required. R13R14 and R15 are hydrogen atoms and methyl.

Here, examples of the alkali metal salts include lithium salts, sodium salts, potassium salts, etc., and examples of the alkaline earth metal salts include calcium salts, magnesium salts, etc.

R18 is the same or different and is a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms.

The hydrocarbon group having 1 to 10 carbon atoms refers to a hydrocarbon group having 1 to 1 carbon atoms.
0 aliphatic hydrocarbon group, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and an aromatic hydrocarbon group having 6 to 10 carbon atoms.

The aliphatic hydrocarbon group is linear or branched, saturated or unsaturated, and includes, for example, methyl, ethyl, various propyl, butyl, hexyl, octyl, decyl, various propenyl, hexenyl, Nonenyl, etc., or those substituted with an alicyclic or aromatic hydrocarbon group, such as cyclohexylmethyl, cyclohexylpropyl, phenylmethyl, phenylethyl, etc., among which those having 1 to 8 carbon atoms are mentioned. preferable.

Examples of alicyclic hydrocarbon groups having 3 to 10 carbon atoms include cyclopentyl, cyclohexyl, various types of methylcyclohexyl, dimethylcyclohexyl, diethylcyclohexyl, cyclohexenyl, and various types of dimethylcyclohexenyl. is preferably 3 to 8.

Furthermore, examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl, various types of toluyl, diethylphenyl, naphthyl, methylnaphthyl, and the like.

Such R16. Preferred hydrocarbon groups as R17 and R18 are saturated aliphatic or alicyclic hydrocarbon groups having 1 to 8 carbon atoms, and hydrogen atoms are also preferred.

Preferred functional salts of α,β-unsaturated carboxylic acids represented by general formula (I) in terms of herbicidal activity in the present invention are alkali metal salts and salts with ammonia, such as ethylamine salts, diethylamine salts, and dimethylamine salts. , propylamine salt, dipropylamine salt, cyclohexylamine salt, octylamine salt, etc.

Examples of the pyridyloxy aliphatic carboxylic acid derivative of formula (I) include the following compounds, but the present invention is not limited thereto.

Cl-l1lQ The compound of the above formula (I>) can be produced, for example, by the following reaction method.

In addition, the functional salts of the general formula (I) above can be added to a predetermined alkali metal compound, such as water, in water or an organic solvent such as methanol, ethanol, chloroform, or ethyl acetate, or without a solvent. Hydroxides such as sodium oxide and potassium hydroxide, and ammonia.

'Aa can be obtained by reacting with amines.

Furthermore, the pyridyloxy aliphatic carboxylic acid (compound A) of the present invention exhibits non-selective herbicidal activity when R11 is an alkyl group having 1 to 5 carbon atoms, and when R1 is a hydrogen atom, it inhibits broad-leaved weeds. It has the characteristic of exhibiting selective herbicidal activity that selectively kills weeds.

The compound of the above formula (I) of the present invention can be applied to the seeds of plants, and can also be applied to plants at various growth stages via the foliage or roots.

That is, the compounds of the present invention, as such or in the form of a composition, can be used in plants whose metabolism is to be regulated, seeds of such plants, places where such plants grow, or where such plants grow. Where it is expected that
It is applied with enough mother to regulate the plant's metabolism.

The compound of the present invention is, for example, 0.1 g to 2 K per 10 ares.
g, more preferably from 0.5 (] to 1 Kg, particularly preferably from 1 g to 500 g, can regulate the metabolism of the plant.

When the purpose of using the compound of the present invention is to suppress or exterminate the growth of harmful plants, the compound of the present invention, either as it is or in the form of a composition, is applied to these plants in a place where the harmful plants or their seeds survive or are likely to survive. Alternatively, it can be applied directly to seeds or to soil at a level sufficient to suppress or exterminate the growth of harmful plants.

In general, a herbicide containing a mixture of the compound (A) of the present invention and an N-phosphonomethylglycine derivative represented by the following general formula (■; or a strong acid salt thereof (compound B)) as the main active ingredient is used. This makes it an even more active herbicide.

The compound of the above general formula (n) is an N-phosphonomethylglycine derivative, in particular, the isopropylamine salt of N-phosphonomethylglycine is a compound known as Roundup ■ (Japanese Patent Publication No. 56-6401 (see Publication No.)) It is a non-selective herbicide.

In the above formula (n), R21, R22 and R23 are the same or different 10H, -0R24 or -NR25
It is R26.

Here, R24 is an alkyl group or a cyclohexyl group.

It is selected from the group consisting of halo lower alkyl group, lower alkenyl group, lower alkoxy lower alkyl group, hero lower alkoxy lower alkyl group, lower alkoxy lower alkoxy lower alkyl group and phenoxyethyl group.

R25 and R26 are the same or different and are hydrogen atoms.

An alkyl group to hydroxyalkyl group having 1 to 4 carbon atoms, an alkenyl group to hydroxyalkyl group having 2 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, and R25
and R26 can be combined with a nitrogen atom to form a morpholino group, a piperidyl group or a pyrrolidyl group.

In addition, when R21, R22 or R23 represents 10H, they are an alkali metal or an alkaline earth metal.

Salts can be formed with cations selected from copper, zinc, ammonium and organic ammonium ions.

Here, the alkali metal represents lithium, sodium or potassium, and the alkaline earth metal represents magnesium or calcium.

The organic ammonium salt of the above formula is a low molecular weight organic amine,
that is, prepared from amines having a molecular weight of about 300 or less, and examples of such organic amines include, for example, alkylamines, alkylene amines and alkanolamines having not more than two amine groups, ethyl amines, n-propylamine, isopropylamine, n-butylamine, isobutylamine, secondary
-butylamine, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine,
Dodecylamine.

tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylhbutylamine,
Ethyl octylamine, hexylhebutylamine, hexyl octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-amylamine, diisoamylamine, dihexylamine, di-heptylamine.

Dioctylamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine,
Tory secondary butylamine.

Tri-n-7 milamine, ethanolamine, n-propanolamine, isopropanolamine.

Jetanolamine, N,N-diethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl -2-amine, di-butenyl-2-amine, n-hexenyl-2-amine and propylene diamine, primary
arylamines such as aniline, methoxyaniline, ethoxyaniline, o,m,p-toluidine, phenylenediamine, 2,4.6-tribromoaniline.

Benzidine, naphthylamine, o, m, p-chloroaniline, etc.: Heterocyclic amines such as pyridine.

Examples include morpholine, piperidine, pyrrolidine, indoline, and azepine.

Preferred compounds (8) in the present invention include at least one of R21, R22 and R23 in the above formula is a salt of 10H or 10R24, and R21,
Examples include compounds in which the remainder of R22 and R23 is 10H or a salt thereof.

More preferred compound (B) in the present invention is at least one of R21, R22 and R23 mentioned above.
is a salt of -OH, and R21, R22 and R2
Compounds in which the remainder of 3 is 10H can be mentioned. Here, the salts of -○H include ammonium or organic ammonium (here, the organic ammonium group is monoalkylammonium, dialkylammonium, trialkylammonium, or monoalkenylammonium).

and such The organic ammonium group has 1 to 18 carbon atoms).

When the herbicide of the present invention is used in the form of a mixture of the compounds represented by the above general formula (1) (compound A) and general formula (■) (compound B), when used, the herbicide in the composition is The composition of each component depends on the relative activity of the above two components, the type of target plant, etc., but generally Compound A and Compound B are mixed in a weight ratio of 1:50 to 50:1. Preferably 1:2
The content is in the range of 0 to 20:1, particularly preferably 1:10 to 10:1.

The actual amount of the composition to be applied will depend on a number of factors, such as the type of particular target plant to be inhibited, but will generally range from 10 to 1000 g/10a, preferably from 50 to 500 g/10a. A suitable amount is 10a.

Those skilled in the art can easily determine the appropriate proportion and amount to use by standard and routine tests without having to perform a particularly large number of experiments.

The mixtures according to the invention can also be applied in the form of compositions in which the active ingredient is mixed with a carrier consisting of a solid or liquid diluent. Additionally, the composition may further contain additives such as surfactants.

According to the present invention, compound (A) and compound (B) can be mixed together to kill weeds as a composition, but these compounds can also be applied separately in any order. The timing of use is preferably before the herbicidal activity of one of the compounds is expressed, and although it varies depending on the target plant, climate conditions, etc., it is preferable to apply the other within 2 to 3 days immediately after applying one. In that case, compound (A) and compound (B
) and the amount to be applied are appropriately within the ranges described above. In view of the herbicidal effect and practical aspects, it is preferable that compound (A) and compound (B) be mixed and applied simultaneously as a composition.

Furthermore, the compound of the present invention or a composition containing the compound of the present invention exhibits excellent herbicidal activity against weeds to be weeded by killing or inhibiting their growth, especially when sprayed on the foliage of the weeds.

The composition of the present invention can be prepared as a solution or emulsion by containing it together with a carrier and/or a surfactant.

It can be used as a preparation in a conventional form such as a suspension, powder or paste.

Such preparations include, for example, talc, bentonite.

Clay, kaolin, diatomaceous earth, white carbon.

Solid carriers such as vermiculite, slaked lime, ammonium sulfate, urea, etc.:
water, alcohol, dioxane, acetone.

xylene, cyclohexane, methylnaphthalene.

Liquid carriers such as dimethylformamide; alkyl sulfates, alkyl sulfonates, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monoalkylate, dinaphthylmethane disulfonate, etc. surfactants, emulsifiers or dispersants;
It is prepared using one or more of various auxiliary agents such as carboxymethyl cellulose and gum arabic.

That is, such a formulation can be prepared, for example, by mixing Compound A and/or B with the carrier and/or emulsifier as described above.

The compositions of the present invention generally contain 0 of Compounds A and B in the formulation.
．． It may be present in a proportion of 0.01 to 99%, preferably 0.1 to 1%.

The compositions according to the invention can be used, for example by spraying, atomizing, dusting or dusting, on their own or in admixture with other active compounds or in the form of preparations as mentioned above.
It can be applied to plants by conventional methods such as ting.

The weeds referred to in the present invention include, for example, various weeds belonging to the following families.

Gramineae: sorghum halepens
e) Oat (Avena fatua)
Setaria faberi, Agropyron repens, Panicum texanum, Ec
hinochloa crus-galli) Setaria viridis Poa annua Eleusin
e 1ndica) carpet grass (Axonopu
Bachia s affinis)
ria platyphylla) Umanochahiki (B
romus tectorum) Cyn
odon dactylon) Pani
cum dichotomiflorum) Paspalum dilatatum Echinochloa colona Panicum capillare Kinfu: 1 bite (Setaria glanca) Hydrangea (
AmaranthaCeSe): Aobee x (Am
aranthus retroflexas) dogfish 1
(AmaranthUS 1ividus) Convolvu! aceae; Ipomoea purpurea Cuscuta joponica Polygonaceae (Po)
lyaonaceae) :Freckle (Polyg
onum convolvulus) Willow knotweed (Po
lygonum hydropiper)
r'olygonum 1apaiEl! folIum
) Chenopodiaceae: Chenopodium (ChenOpdiUm album) Chenopodiaceae (C
henopodium album var, cent
rorubrum) Chenopodium
ficifolium) Portulaceae (POrtul)
aCaeeae) : Portulaca x (Portula
ca oleracea) Fabaceae (Le(]lJmin
O3ae): Desmodium to
rtuosum) Malvaceae: Abutilon theophrasti
Sida 5pinO5a Solanaceae (SOIanaCeae): Sida 5pinO5a
IanUm nigrum) Atula stramonium (()atula stramonium) Asteraceae (C
ompositae): Himedion (Eriger)
on annuus) Ambrosia a
rtemisiaefolia Var.

Xantium atrumrium CirSium arVenSe
Var.

setosum) e. Example Hereinafter, the present invention will be described in detail with reference to Examples.

In the examples, parts mean parts by weight. In addition, herbicidal activity was evaluated on a 6-grade scale unless otherwise specified. That is,
After the application of the active compound, the plant is in almost the same healthy state as before application, which is rated O, and when the entire plant wilts and dies as a result of the application of the active compound, it is rated 5, and in the meantime, depending on the weakened state of the plant, it is graded into 4 stages (1, 1, 2, 3 and 4) were established and evaluated.

Example 1 Example 2 2.9 parts of 2-hydroxy-4-(2-chloro-4-trifluoromethylphenoxy)pyridine, 1.82 parts of ethyl 2-bromopropionate, 1.8 parts of anhydrous potassium carbonate. After heating and refluxing a mixture of 4 parts and 20 parts of methyl ethyl ketone for 5 hours, after cooling, 50 parts of ethyl acetate and 100 parts of water were added and shaken. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. .

The residue was recrystallized using benzene and hexane to obtain 3.1 parts of the desired product. NMR and I of this compound
The R spectrum is shown in Table 1.

In Example 1, 2-hydroxy-4-(2-chloro-
2-hydroxy-4-(3-chloro-5-trifluoromethylpyridin-2-yloxy)pyridine 2 instead of 2.9 parts of 4-trifluoromethylphenoxy pyridine
．． By reacting and post-treating 9 parts under the same conditions, 3.0 parts of the desired product was obtained. NMR and I of this compound
The R spectrum is shown in Table 1.

Example 3 In Example 1, ethyl 2-bromopropionate 1.8
Using 1.23 parts of ethyl chloroacetate in place of 2 parts, the reaction and post-treatment were carried out under the same conditions to obtain 2.8 parts of the desired product. The NMR and IR spectra of this compound are
Shown in the table.

Example 4 In Example 1, 1.8 ethyl 2-bromopropionate
Methyl 2-bromopropionate 1.67 instead of 2 parts
2.7 parts of the target product were obtained by reaction and post-treatment under the same conditions. The NMR and IR spectra of this compound are shown in Table 1.

Example 5 In Example 2, 1.8 ethyl 2-bromopropionate
n-butyl 2-bromopropionate instead of 2 parts.
1 part was reacted and post-treated under the same conditions to obtain 2.9 parts of the desired product. , NMR and IR of this compound
The spectra are shown in Table 1.

Example 6 ω H3 1.0 part of the compound obtained in Example 1 was added to 10 parts of ethanol.
After adding 0.5 part of 38% aqueous ammonia and stirring overnight at room temperature, the ethanol was concentrated, 20 parts of water was added, and the mixture was extracted with ethyl acetate. After drying the organic layer over anhydrous sodium sulfate, the solvent was removed under reduced pressure to obtain 0.6 part of the desired product. The NMR and IR spectra are shown in Table 1.

Example 7 ω Dissolve 3.7 parts of the compound obtained in Example 1 in 20 parts of ethanol, add 15 parts of 1N hydrium hydroxide aqueous solution, stir overnight at room temperature, concentrate the ethanol, and acidify with dilute hydrochloric acid. The mixture was extracted with ethyl acetate.

After drying the organic layer over anhydrous sodium sulfate, the solvent was removed under reduced pressure to obtain 3.2 parts of the desired product. NMR and I
The R spectrum is shown in Table 1.

Example 8 ω 3.32 parts of 1N sodium hydroxide solution was added to 1.2 parts of the compound obtained in Example 7, and the mixture was stirred at room temperature until a homogeneous solution was obtained. Thing 1.
Obtained 27 copies.

Example 9 Q 0.3 parts of isopropylamine was added to a mixture of 1.2 parts of the compound obtained in Example 7 and 10 parts of water, stirred at room temperature until a homogeneous solution was obtained, and then the water was dried under reduced pressure. Objective 1
．． I got 3 copies.

Example 10 ω In Table Example 1, ethyl 2-bromopropionate 1.8
Using 1.94 parts of N-isopropyl-2-bromopropionamide instead of 2 parts, the reaction and post-treatment were carried out under the same conditions to obtain 3.0 parts of the desired product.

The NMR and IR spectra of this compound are shown in Table 1.

No. Table (continued) No. Table (continued) No. Table (continued) I used what I had cultivated.

The plants were treated with a preparation containing the active compounds of the invention in such a manner that each active compound formed a defined chain, and cultivation was then continued for 3 weeks without application of the preparation.

The results are shown in Table 2.

Preparation Example: Add 1 part of the active compound of the present invention to 5,000 parts of a mixed solution of acetone and water (volume ratio 1:1), add 2.6 parts of a nonionic surfactant (trade name: Tsurupol 268G), and prepare a solution. was prepared.

Test example 1 The active compounds of the invention were prepared according to the formulation examples given above.

Plant seeds are sown in soil and cultivated for 2 to 3 weeks after germination Comparative Example 1
~2 and Examples 11 to 14 (Compound A') and isopropylamine salt of N-phosphonomethylglycine (Compound B') were each mixed with water at a predetermined mixing ratio and a predetermined treatment amount. Acetone mixed solvent (volume ratio 1:1. Nonionic surfactant: trade name 5O
RPOL-268080 (containing 05%) was dissolved in 16 parts to prepare a spray solution.

Plants are placed in plastic pots (10 cm in diameter) filled with soil.
), which were cultivated in a greenhouse for 2 to 3 weeks after germination by sowing or rhizome transplantation.

The above preparation was applied to this plant at a total spray volume of 4 CC/10
The herbicidal activity was examined by applying the solution at an area of 0 cm2.

The results are shown in Table 3.

As explained in detail in the f0 invention, the present invention provides a non-selective herbicide that has a wide herbicidal spectrum by varying R11 and a selective herbicide that selectively kills broad-leaved weeds at low doses. Furthermore, the herbicide according to the present invention is a fast-acting herbicide that exhibits a herbicidal effect within 2 to 3 days after application. In addition, by mixing it with currently known herbicides, it becomes a more rapid-acting non-selective herbicide.

Claims (6)

[Claims] (1) The following general formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼... (I) [In the formula, X and Y are the same or different, hydrogen atom, -
CF_3 is a halogen atom, and either X or Y is -CF_3. Z represents =CH- or =N-, and R^1^1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms. R^1^2 is a group represented by -OR^1^3 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼. Here R^1^3
is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R
^1^4 and R^1^5 are the same or different and are a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and R^1^
4 and R^1^5 may cooperate with each other to form a ring. A and B are the same or different and are oxygen atoms or sulfur atoms, and they are in meta positions with respect to each other. D is a nitrogen atom, which is ortho or distal to A or B, and never ortho to both A and B. ] A novel pyridyloxy aliphatic carboxylic acid derivative represented by or its salts when R^1^3 is a hydrogen atom (
Compound A). (2) A herbicide containing the compound according to claim 1 as a main active ingredient. (3) A non-selective herbicide containing as a main active ingredient a compound represented by the above general formula (I) in which R^1^1 is an alkyl group having 1 to 5 carbon atoms. (4) A selective herbicide for broadleaf herbicides containing as a main active ingredient a compound in the above general formula (I) in which R^1^1 is a hydrogen atom. (5) Compound (A) according to claim 1 and the following general formula (II)
▲There are mathematical formulas, chemical formulas, tables, etc.▼...(II) In the formula, R^2^1, R^2^2 and R^2^3 are the same or different -OH, -OR^2^4 or - NR^2
It is ^5R^2^6. Here, R^2^4 is an alkyl group, a cyclohexyl group, a halo-lower alkyl group, a lower alkenyl group, a lower alkoxy lower alkyl group, a halo-lower alkoxy lower alkyl group, a lower alkoxy lower alkoxy lower alkyl group, and a phenoxyethyl group. To be elected. R^2^5 and R^2^6 are the same or different and are a hydrogen atom, an alkyl group or hydroxyalkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 4 carbon atoms, and R
^2^5 and R^2^6 can be combined with a nitrogen atom to form a morpholino group, a piperidyl group or a pyrrolidyl group. In addition, R^2^1, R^2^2 or R^2^3 is -O
When H is represented, they can form salts with cations selected from alkali metals, alkaline earth metals, copper, zinc, ammonium and organic ammonium ions. However, 2 of R^2^1, R^2^2 or R^2^3
More than one is -OR^2^4 or -NR^2^5R
It cannot be ^2^6. Also R^2^1, R^
When either 2^2 or R^2^3 is -OH and the -OH is an ammonium salt or an organic ammonium salt, R^2^1, R^2^2 or R^2^ No more than two of 3 are said salts. A herbicide containing an N-phosphonomethylglycine derivative represented by the following formula or a mixture thereof with a strong acid salt (compound B) as a main active ingredient. (6) The seeds, stems, leaves, and roots of the plants to be weeded with the compound A and the compound B at the same time or in any order, or where the plants are growing or where the plants are expected to grow. A weed control method characterized by applying a sufficient amount to kill weeds to the location where the weeds are to be removed.