JPH0377874A - 1,3,5-triazine-2,4-(1h,3h)-dione derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I [R is H or 1-3C alkyl; R' is CF3 or CH3; G is H or halogen; A is halogen or NO; E is H, halogen, CN, NO2, NH2, OH, SH, CH3, CO2H, OR1 (R1 is alkyl, cycloalkyl, alkenyl, alkynyl, etc.), formula II (R2 is H, alkyl, SCH3, SC6H5, etc.; R3 is H, Na, K, NH4, alkyl, alkenyl, phenyl, etc.), etc.]. EXAMPLE:3-(4-Chlorophenyl)-1,6-dimethyl-1,3,5-triazine-2,4-(1H,3H)dione. USE:A selective herbicide. PREPARATION:A compound expressed by formula III is reacted with a com pound expressed by formula IV to give a compound expressed by formula V, which is then reacted with a halogenophosphoric acid ester or phosgene in the presence of hydrochloric acid and the resultant product is reacted with an alkylating agent to provide the compound expressed by formula I.

Description

[Detailed description of the invention]

[Industrial Application Field] The present invention relates to a novel triazinedione derivative and a selective herbicide containing the derivative as an active ingredient. [Conventional technologies and issues] Many herbicides have been put into practical use to protect important crops such as rice, soybeans, wheat, corn, cotton, beets, etc. from weeds and to increase the productivity of these important crops. It has been. These agents can be roughly divided into three categories depending on the application: upland, paddy field, and non-arable land. Furthermore, among each, soil-mixed treatment type,
It can be classified into pre-emergence soil treatment type, post-emergence treatment (foliage treatment) type, etc. In recent years, as the world's population has increased, it is clear that the productivity of important crops has an impact on the food economy of each country. Along with these changes, it is inevitable that traditional agricultural forms will change as we head into the 21st century. In fact, farmers need more than ever before to develop herbicides that can economically and efficiently kill or control weeds that are a hindrance to crop cultivation. There is a strong desire to develop such herbicides that meet the following requirements. Those that have a high herbicidal effect at a low dose (particularly from the perspective of environmental protection, it is necessary to kill weeds by spraying as low a dose as possible), and those that have a moderate residual effect (in recent years, it is necessary to kill weeds by spraying as low a dose as possible). It is a problem that long-lasting chemicals can damage subsequent crops, so it is important that they have an appropriate residual effect after being sprayed. (After that, the next crop can be sown and transplanted in a short period of time), and the number of chemical treatments is small (it is important for farmers to minimize the number of times they have to perform complicated weed control operations). , Those with a wide range of weed control targets (preferably a single chemical that can control weed species with different characteristics such as broad-leaved weeds, grass weeds, and perennial weeds), and those that require multiple application methods. (By combining soil treatment effect, foliage treatment effect, etc., a more powerful herbicidal effect can be obtained.), and those that do not cause harmful chemical damage to crops (in cultivated land where crops and weeds coexist). It is desirable to have a herbicide that can selectively kill only weeds.However, existing herbicides do not meet all of these conditions. On the other hand, it is known that certain compounds of triazinedione derivatives exhibit herbicidal activity; for example, The Pe5
ticide Manual 8th edition, page 461 The
Br1-tish Crop Protection
Council (1987) et al. described hexazinone as a herbicide with a triazinedione skeleton.
one) is described, but the application amount is 6-12 k
g/ha and poor selectivity for crops, so it is difficult to say that it is an excellent compound as a herbicide. [Means for Solving the Problems] In view of this situation, the present inventors have developed a compound that exhibits selectivity for important crops and has excellent herbicidal effects against many weeds at low doses. As a result of continuing research to develop a herbicide that has both soil treatment and foliage treatment effects, the formula (1)

[In the formula, R represents a hydrogen atom or Cl-Cs alkyl, R' represents CF or CFI3, G represents a hydrogen atom or a halogen atom, and A represents a halogen atom or NO
g, E is a hydrogen atom, a halogen atom, CEN,
NOl,NL-,OH,,5R1CH3,GO2H
1ORI [However, R1 is Co-Cs alkyl, Cl-C
l cycloalkyl, Cs-Ca, cycloalkyl (CI
-CX) alkyl, CZ-C4 alkenyl or Cl-
Indicates C4 alkynyl. ]-0-CHCOR3 (However,
R2 is a hydrogen atom, Cl-Cs Al2kyl, SCH, 5CiHs or CHzO (Jz), R3 is a hydrogen atom, Na, K, NIL4, G
o-Cs alkyl, cg-cs alkenyl, Cs-Cs
Alkynyl, C5-Chcycloalkyl, Cl-ChcycloalkylCC+-CZ)alkyl, C,-C3 haloalkyl, phenyl, phenethyl or benzyl. ), C0J4 (However, R4 is C, -C, alkyl, C,
I"C6 represents cycloalkyl, phenyl or benzyl.], coxes□C0gR5 (wherein, R5 represents a hydrogen atom or CJ-C11=alkyl), 6C=NOCHiCOmR7 (however, Ii[6 represents a hydrogen atom, Cl -C5 alkyl, CI-C, alkoxy or C
,-(,I represents alkylthio, R7 is a hydrogen atom, CI
-C4 alkyl, C5-Ct, cycloalkyl, C+
+-Cs represents haloalkyl, phenyl or benzyl. ], Kyl, C, -C, alkoxy or CI-Cl1alkylthio, R9 represents a hydrogen atom or CB, R
IO represents a hydrogen atom, Cl-C4 alkyl, Cl-(1, cycloalkyl, C2-C2 haloalkyl, phenyl or benzyl.) 11 C1(, VCHCO2R12 (However, Y represents an oxygen atom or a sulfur atom, R11 Hydrogen atom or C, -C3
5R13 (however, R13 is Cl-Cs alkyl, C5-
Chcycloalkyl, CM-〇, argenyl, Cs-C
aalkynyl, CI, Cl, CHgOH or en
*Indicates ez. ], ■ 5CHCOR15 (However, R14 is a hydrogen atom, Cj-C
3Aruki14 Le, SCU,,SC&! (or CHzOCHs, R15 is a hydrogen atom, Na, NH,, NHsCH
(CHs)t, Cl-Cs alkyl, Cx-Cs alkenyl, Cs-Cs alkynyl, C, -C, cycloalkyl, C, -Ch cycloalkyl (ci-cz) alkyl, C, -C, haloalkyl, phenyl, benzil,
Phenethyl, α-methylbenzyl, CHz (IlmCH
J (CHs)! , substituted phenyl (however, substituted phenyl refers to a phenyl group which may be optionally substituted with one of the following substituents; halogen atom, Cl-C4
1) k-kyl, Cl-Cs alkoxy, Go-Cx alkylamino, N(CHs)*, C0z-(CI-Cx
alkyl), C, -C, alkylcarbonyl, Cr-C
s haloalkyl or Ci 4g haloalkyl)
or substituted benzyl (however, substituted benzyl does not refer to a benzyl group that may be optionally substituted with the following substituents; halogen atom, C, -C, argyl, Cl-Cs
Alkoxy, Cr-Cx alkylamino, N(CL)2
, C, -C, alkylcarbonyl, NHCOCF3,
C0g4Ci-C, alkyl), SOt side 8.5 (J
tCFs, CI-Cs haloalkyl or CI-CI!
haloalkyloxy). ]SCTo-(CHg
-), C0zR15 [However, n represents an integer of 1 to 4, and R15 represents the same meaning as above. ], SCH! 4-
Rl6 (However, Y has the same meaning as above, and R16 represents a hydrogen atom, C, -CS alkyl, CHffiCN. C0-(C1-C4) alkyl, cocozcl or C0N(CTo)z,] 5(Jz −■−(J(R14)C0zR15(However, Y
, , R14 and R15 represent the same meanings as above. ], SGHz-Y-C11g-←CI(!U* C0J15
(However, Y,, n. R15 represents the same meaning as above.), SCH*4-P
(0) (OR17) x (However, Y represents the same meaning as above, R17 is a hydrogen atom, C, -C, alkyl,
) represents enyl or benzyl, ] or ] 5CHffi-Y-PS) (OR17)! (however,
Y, R17 represents the same meaning as above, ] represents, ], but when A and E form a ring, the formula (
II) or formula (■):

[In the formula, G and Z have the same meanings as above, and J is a hydrogen atom, Cl-Ca alkyl, CHzOH, CHzCj!
. Ct-Cs alkenyl, C3-Ca alkynyl, CHz
CN -CIl□C0NHz or benzyl, ]
The triazinedione derivative represented by (hereinafter referred to as the compound of the present invention) can be used as a herbicide for upland and paddy fields, in both soil treatment and foliage treatment, for the treatment of grasshoppers, datura, Japanese radish, and goldenrod. Mosquitoes, morning glories, golden locusts, green locusts, onus fir,
Pigweed, sunflower, leaf-flowering, staghorn thistle, wildflower, serpentine, dogwood, field mustard, shepherd's purse, Japanese knotweed, buckwheat, purslane, whiteweed, koakaweed, broomweed, chickweed, giant dogweed,
Broad-leafed weeds such as dayflower, hotokenoza, black-and-white wattle, blackberry, blackberry, japonica, madder, violet, black-and-white, black-and-white weed, wild turgid gum, japonica japonica, johnson grass, dogweed,
Weeds of the grass family, such as grass grass, oat, ohiba, foxglove, and sycamore; Cyperaceae weeds, such as cyperus grass; various types of rice fields, such as grasshopper, omodaka, omodaka, urikawa, cyperus japonica, cypress japonica, scallop, black guinea, azalea, japonica, hirumushiguchi, kikashigusa, and Japanese millet, etc. It has a high impact on weeds with a low dosage. Also important crops are wheat, corn, barley, soybeans, rice, cotton,
Safe to use on nuts, beets, turgsum, etc. Compared to conventional herbicides, the compound of the present invention has a high herbicidal effect at an extremely low dosage and is fast-acting, and can be applied to a wide variety of weeds by both soil treatment and foliage treatment. This is a major feature. The compounds of the present invention can be synthesized, for example, by the methods shown in Schemes 1 and 2 (R5R', G, A in Scheme 1.2).
, E indicates the same meaning as above, examples of the halogenoformate include ethyl chloroformate, methyl bromoformate, etc., phosgene may be used as a monomer or trimer, and the alkylating agent includes, for example, methyl iodide. , ethyl iodide, dimethyl sulfate, etc., and examples of the base include sodium hydride, potassium carbonate, sodium hydroxide, etc. ). Synthesis examples of the compounds and intermediates of the present invention will be specifically described below as reference examples, but the present invention is not limited thereto. Synthesis of N-(4-chlorophenyl)carbamoylacetamidine NH. 5. Add 50% aqueous sodium hydroxide solution to a mixture of 6.16 g of acetamidine hydrochloride and 65 n/2 water at 10°C or below.
60 g was added. 130aJ of acetone at the same temperature!
and then 4-chlorophenylisocyanate 10.
Og was added gradually. After raising the temperature to room temperature for 3 hours, acetone was removed under reduced pressure, extracted with chloroform, dried over anhydrous sodium sulfate, and chloroform was removed under reduced pressure to obtain 10.5 g of the target compound as white crystals. Melting point 123.5-125°C 'H-NMR (CDC12s) δ: 2.00 (3
H, s), 7.23 (2H, d, J-9Hz),
7.73 (2B, d, J-9H2), 8.10
(2H, s), 9.34 (IH, br s) 1 support 1 3-(4-chlorophenyl)-6-methyl-1°3.5
-) Synthesis of riazine-2,4(IH,3H)-dione tetrahydrofuran 20tai! , sodium hydride (
0.40g of the mixture (purity 60%) was heated with N-
(4-chlorophenyl)carbamoylacetamidine 1
．． 00 g was added. After 30 minutes ethyl chloroformate 0.5
After adding 1 g of the mixture and raising the temperature to room temperature, the mixture was refluxed for 1 hour. After removing tetrahydrofuran, ice water was added, acidified with dilute hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then ethyl acetate was removed to obtain a crude product. This was washed with diisopropyl ether to obtain 0.51 g of the target compound as pale yellow crystals. Melting point 275-276°C 'H-NMR (di-DMSO) δ: 2.23
(3H, s), 7.11 (2H, d, J=9Hz)
, 7.36 (2H, d, J=9Hz), 10.0~
12.0 (1B, br s) Reference 1 3-(4-chlorophenyl)-1,6-cymethyl-1.
3. Synthesis of 5-1-riazine-2,4(IH,3H)-dione (inventive compound Na198) ■ CHs To a mixture of 3-1 dimethylformamide and 0.06 g of sodium hydride (purity 55%), add 10 3-(4
0.30 g of -chlorophenyl)-6-methyl-1°3.5-triazine-2,4(IH,3H)-dione was added. After 30 minutes, raise the temperature to room temperature and add 0.24 g of dimethyl sulfate.
was added and stirred for 3 hours. After removing dimethylformamide, ice water was added and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with saturated brine, dried over anhydrous sodium sulfate, and then ethyl acetate was removed to obtain a crude product. This was purified by preparative thin layer chromatography (developing solvent: hexane-ethyl acetate 1:1) to obtain 0.05 g of the target compound as yellow crystals. Melting point 204-206.5°C 'H-NMR (CDCffi3) δ: 2.52
(3H, s), 3.50 (3H, s), 7.25 (2H, d, J=9Hz), 7.56 (2
H, d, J-9Hz) Next, the compounds of the present invention synthesized according to the above reference examples or schemes are shown in Table 1-3, including the compounds synthesized in the above reference examples. It is not limited to these. (Leaving space below) Table 1 (Continued) OCR (CHs)z OCR□Cl-CH! 0CHzCHmiCH OCHzC(hH OCRICOIC113 OCHzC0gC11(s OCH*COz < 0CHzCOrichCHxCHtCI OClbCOmCthHs Q(JICOICIIICJI OCR(CHs) C0 zCHs OCR(CHs)CO*C*Hs OCH(SCFis)C0zCHs OCR(SCHs)COgC*Hs Compound inhibition table (continued) CotICH3 OgCJs co, J CO, (, l5 COa+CRxCaHs CHsCH*C0J CI-NOCHxCO*CHs C(C11s)=NOC1(2CO1CLC(CHm)
=NOCI! GO, C1! N5C(OCHs)=NOC
HzCOJ C(OClh)=NOCHzCOzCthC(OCHs
)=NO(JtCO*CJsC(SCHs)JOCHz
COzCHsCH=NN=C((Js)COzcHs5
CH8OH SCH,cF! SCH (SCHs) COgCHs SCH (SC&1Is) COICI. 5CH(CHtOcHz)CO□CH35C)I(CT
oOCH3) CO8C! HsSCH(CRs) COg
CHs SCI((C1h)C(hCJs scocen3)Co!enle&+(iiSCI((
CtHs)GOICH3 SCH(CJs)CHsCJs SCHzCO2H 3CHiCOgCI(s SCLCOgC*lIs Table 1 (continued) C(CL)=NN, C(CL)COIC!HsC(0(
J3)-NN,,C(CI3)CO,CHsC(OCR
3bNN-(JfCOa(J, IC(SCHs)JN-
C(CHs)C(hclbCHffiOCToCOgC
I3 (J*0CR(CTo)COtCHr CToSCH++CO++CHs CToS(J((Js)CO□CtoSCI? (Cl□)8 SCHxClbCHg SCH2CECI( scullcN Table 1 (continued) S(JbCOzCHzCToC T. 5CHZCO*(Js SCHENG CO++CI( CHs) ! 5CLCOzCH PACTo) *CT. 5CHzCOxCHzCH(CHs) tSCI(EC
OH(CHi)CJs SCHzCOxC(CI3) , 1 SCI((C83) C00H SCH(C1Hs) C00H SCHICOyClhbe○ 5CLCL=CToCHyaCl 5CHxCOrCJs SCHz(ells)COzCH *CゎH2 table (continued) SCHzCOzC)l( CHi)CallsSCHIC
o□C11zCHzCHJ((Hg) zSCHzCO
,-2-chloro-phenylSCHzCO,-
3-chloro-phenylSCHzCO, -4-
chloro-phenylSCHtCOz-2-me
thoxy-phenylSCHzCOl-3-met
hoxy-phenylSCHtCOz-4-meth
oxy-phenylSCHzCOt-2-NHCtH
s-phenylSCHzC(h-2-N(C)Ii)
z-phenylSCHzCO, -2-CO, CHi
-phenylSCHzCO, -3-CO,CHz-p
henylSCHtCOz-2-COCL-pheny
lSCHtCOz-2-CFx-phenyll Table (
Continued) SGHzGO, 3-methyl-phenylSCH
, CO, -4-sethyl-phenylSC)12
COz-2-methoxy-benzylSCHtC
o,-3-methoxy-benzylS(:l,(
:Q, -4-@6thoxy-benzylSCHzC
Oz-2-NHCHff-benzylSCHICO2
-2-NHCzHs-benzylSCHzCOt-2
-N(CL)z-benzylSCHtCOt-2-C
OCHs-benzylSCHzCOt-2-NHCO
CFs-benzylSCH, CO, -2-COzCH
s-benzylSCH, CO, -3-CO, CHs-
benzylSCH, COz-4-CO, CHs-be
nzylSCH, CO2-2-5O2CH3-benz
ylSCH, CO, -2-SO, CF+-benzyl
Table 1 (continued) SCHtCO, 2-fluoro-phenylSCH
gCOl-3-f 1uoro-phenylSGHz
CO, -4-fluoro-phenylSCHzCO
g-2-chloro-benzylSCHICO,-
3-chloro-benzylSCHgCO, -4-
chloro-benzylSCHgCO1-2-f
1uoro-benzylSCHLCOl-3-fl
uoro-benzylSCHgCO, -4-fluo
ro-benzylSCHtCOt-2-ethyl-
benzylSCHxCO, -2+4-difluor
o-benzylSCHgCO2-3+ 4-di f
luoro-benzylSCHgCOg-2-se
thyl-benzylSC) itco, -3-set
hyl-benzylSGHzCO,-4-setby
l-benzyl Table 1 (continued) SCHtCOt-2-OCFtH-benzylSCL
COt-2-OCFs-benzylSCHxCHtC
OtCHs SCHzC[1tCQtCtHs SCHt + CHz ÷C0tCH*5CHt +
CI! JuchoC0zCJsSCHt-+CI(t+rc
Ot < 5C) I r ten (AI z Imacho Co zcHIC8z
c lSCHg + CI! ImachoC0zCHzCJsS
CHt + Cut +-1-C(h(:l5SCH*
+ CH*÷DingC0zCJsSCL+C■*+rCO
z < 5CHt-+CH1+TCOICH1 SCHz+CHI→τCO□CtHs SCH*+CL-+rCO! < SCH*SH Table (continued) Table 1 (continued) SCH*SCH! 5CHxSCHiCN SCHxOCIb SCtbOCHlCN SCToOCO(Js SCToOCOCHzCl 5CToOCON(CHs) *SC) [*0CHzCOzCHs SCHxOCToCOzCJs SCHxOCToCOl o SCI'! tOcH(CIriCDtCH!5CHtOC
R(CLOCHs)COzCH3SC1fLzOCH(
CLOCIb)COxCJsSCHzOCH(SCHs
) C0xCHsSCToOCf[(SCHs)COg
G++flsSCHzSCHsCOxCHs SCtbSCH(CHriC(hc*HsSCHsOCH
*CHtCOxCHs SCH! 0CHffi+ CHrchi■C0xCtlsS
CHtSCTo+ CHs-+TCo寥CHsSCHt
OCHs + CHr) DingCO*CH35CHtOP
(0) (OCJs)寥SC)IgOP (S) (O
CRs) zSCH*OP (0) (OCRs) z
sen*opcs) (OCJs) t OCHzCOsNa OCH(CH3) CO NH3CI((CHs) z
SCHtCOtNa S(JbCOJ SCHiCOtNH4 SCHxCOJHsCH(CH3) Table (continued) Table 1 (continued) SCH(CHs)COJ SCH(CH3)C0tNH3CH(CL)t■ 5CHICO□C113 SGHzCOzC Js SCToCOz -Q OCR,CO□Cf!. OCR (CHs)COtells SCH(CHs)COzCHs SCH(CHs)COtCJs SCHgCOzGHz C(hcHz (hereinafter, blank space) COaCH(CHs)t COiCH(CHs) t ■ Table 2 ■ CtH. CI, 0H C1zC =cHtC) ItC:CI C1zC=cH CH,CEN HzCJs C1+!1 Table 3 R' zHs CHg011 H2C1 CHzCtoCHz cnzc=c. CI(,C:C11 C1,CEN Table 2 (continued) CHtCONIll CIH s C11xCB-CHg C11tC- CH CIIffiCEN CHxCthHs lll5 (Hereinafter, blank) Table 3 (continued) CHgCONlb tHs CHzCH-CHg CHtCmiCH CHgCth)ls CH,CEN CIHs (Hereinafter, blank) When applying the compound of the present invention as a herbicide, generally appropriate Solid carriers such as clay, talc, bentonite, diatoms, white carbon, etc., or water, alcohols (isopropanol, phthanol, benzyl alcohol, furfuryl alcohol, etc.), aromatic hydrocarbons ([ luene, xylene, etc.), ethers (
anisole, etc.), ketones (cyclohexanone, isophorone, etc.), ester M (butyl acetate, etc.), acid amides (
N-methylpyrrolidone, etc.) or halogenated hydrocarbons (chlorobenzene, etc.), and if desired, surfactants, emulsifiers, dispersants, penetrants, spreading agents, thickeners, etc. sticky agents, antifreeze agents, anticaking agents,
By adding a stabilizer and the like, it can be put to practical use in any desired dosage form such as a liquid, emulsion, wettable powder, dry flowable, flowable, powder, or granule formulation. Furthermore, the compound of the present invention may be applied in combination with other herbicides, various insecticides, fungicides, plant growth regulators, synergists, etc. during formulation or spraying, if necessary. As for the type of herbicide to be mixed, for example, the Farm Chemicals Handbook (Farm Chemicals Handbook)
s Handbook) 1989 edition. The amount of the drug to be applied varies depending on the application situation, application time, application method5, cultivated crops, etc., but in general, the amount of active ingredient per hectare (ha) o, ooi
A value of about 5-5 is appropriate. Next, specific formulation examples of formulations using the compounds of the present invention will be shown. However, the formulation examples of the present invention are not limited to these only. In addition, in the following formulation examples, "parts" mean parts by weight. Goon Kunko Wettable powder Compound of the present invention ・・・・・・・・・・・・50 parts Sikrei)-PPP ・・・・・・・・・43 parts (Kaolin based Kreichi Siegrite Kogyo ■Product name ) Tsurupol 5050・・・・・・・・・・・・ 2 parts (Anionic surfactant: Toho Chemical Industry Hatsei brand name) Lunox 100OC・・・・・・・・・ 3 parts (Anionic surfactant Agent: Toho Chemical Co., Ltd. (trade name) Carplex #80 (anti-caking agent)...2 parts (White Carbon: Shionogi & Co., Ltd. (trade name)) The above is uniformly mixed and pulverized to make a wettable powder. L emulsion Compound of the present invention 3 parts xylene ・ ・ ・ ・
・ ・ Part 76 Iso Horon ・ ・ ・ ・ ・ ・ Part 15 Tsurupol 300
5 X... 6 parts (mixture of nonionic surfactant and anionic surfactant: Toho Chemical Industry ■ trade name) or more are mixed uniformly to form an emulsion. [Compound 1- Flowable agent Compound of the present invention 35 parts Agelisil S-711 8 parts (Nonionic surfactant: Kao brand name) Lunox 1ooo c・
・・・・・・・・・0.5 part (Anionic surfactant: Toho Chemical Industry ■Product name) 1% Rhodobol water・・・・・・・・・20 parts (Thickener: Rho・Ethylene glycol (trade name)
Antifreeze agent)... 8 parts water...
...Mix 28.5 parts or more uniformly at °C to make a core pull agent. Granular hydrating agent (dry flowable agent) Compound of the present invention...75 parts Isopane soybean 1...
・・・・・・・・・10 parts (Anionic surfactant: Kuraraytsubu 1/N Chemical ■Product name) Panirex N
・・・・・・・・・・・・ 5 parts (Anionic surfactant: Chūyō Kokusaku Valve - Product name) Force・-Brex #80 ・・・・・・・・・ 1 part (Boyt Carbon: Shiono Gi Seiyaku ■Product name) The above is mixed and pulverized uniformly to make a dry flowable agent. When used, the above-mentioned hydrating powders, emulsions, flowable preparations, and granular hydrating powders are diluted 50 to 1000 times with water and sprayed at a concentration of 0.001 to 2 kg of the active ingredient per hectare. In addition to agriculture and horticulture such as fields, paddy fields, orchards, the compounds of the present invention can be used in railway lines, factory sites, roads, embankments, riverbeds, parks, grounds, cemeteries, school and hospital premises, shrines and temple precincts, Around buildings, substations, tank yards, airports, power line patrol routes, lawns, non-agricultural lands such as golf courses, or pastures;
It can also be applied to control various weeds in lawns, and the amount of application varies depending on the application situation, application period, target vehicle type, cultivated crops, etc., but in general, it is applied to 1 hectare (h
A ratio of about 0.01 to 10 kg per a) is appropriate.

Claims (2)

[Claims] (1) Formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, R represents a hydrogen atom or C_1-C_3 alkyl, R' represents CF_3 or CH_3, and G represents a hydrogen atom or a halogen atom. , A represents a halogen atom or NO_2, E represents a hydrogen atom, a halogen atom, C≡
N, NO_2, NH_2, OH, SH, CH_3, CO
_2H, OR1 [However, R1 is C_1-C_5 alkyl, C_3-C_6 cycloalkyl, C_3-C_6 cycloalkyl (C_1-C_2) alkyl, C_2-C_
4 alkenyl or C_3-C_4 alkynyl. ]、▲There are mathematical formulas, chemical formulas, tables, etc.▼[However, R2 is a hydrogen atom, C_1-C_3 alkyl, SCH_3, SC
_6H_5 or CH_2OCH_3, R3 is a hydrogen atom, Na, K, NH_4, C_1-C_5 alkyl, C_2-C_5 alkenyl, C_3-C_5 alkynyl, C_3-C_6 cycloalkyl, C_3-C_6 cycloalkyl (C_1-C_2) alkyl, C_2-C
_3 Indicates haloalkyl, phenyl, phenethyl or benzyl. ], CO_2R4 [However, R4 is C_1-C_4 alkyl,
C_3-C_6 represents cycloalkyl, phenyl or benzyl. ], CO_2CH_2CO_2R5 [However,
R5 represents a hydrogen atom or C_1-C_2 alkyl. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, R6 represents a hydrogen atom, C_1-C_2 alkyl, C_1-C_3 alkoxy, or C_1-C_3 alkylthio, and R7 represents a hydrogen atom, C_1-C_4 alkyl, C_3-C_6 Indicates cycloalkyl, C_2-C_3 haloalkyl, phenyl or benzyl. ], ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, R8 represents a hydrogen atom, C_1-C_3 alkyl, C_1-C_3 alkoxy, or C_1-C_3 alkylthio, R9 represents a hydrogen atom or CH_3, and R10 represents a hydrogen atom , C
It represents _1-C_4 alkyl, C_3-C_6 cycloalkyl, C_2-C_3 haloalkyl, phenyl or benzyl. ] ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [However, Y represents an oxygen atom or a sulfur atom, R11 represents a hydrogen atom or C_1-C_3 alkyl, and R12 represents a hydrogen atom, C_1-C_4 alkyl, C_3-C_6 cyclo Indicates alkyl, C_2-C_3 haloalkyl, phenyl or benzyl. ], SR13 [However, R13 is C_1-C_3 alkyl, C
_3-C_6 cycloalkyl, C_2-C_4 alkenyl, C_3-C_4 alkynyl, CH_2CN, CH_
Indicates 2OH or CH_2Cl. ]、▲There are mathematical formulas, chemical formulas, tables, etc.▼[However, R14 is a hydrogen atom, C_1
-C_3 alkyl, SCH_3, SC_6H_5 or CH_2OCH_3, R15 is a hydrogen atom, Na,
K, NH_4, NH_3CH(CH_3)_2, C_1
-C_5 alkyl, C_2-C_5 alkenyl, C_3
-C_5 alkynyl, C_3-C_6 cycloalkyl,
C_3-C_6 cycloalkyl (C_1-C_2) alkyl, C_2-C_3 haloalkyl, phenyl, benzyl, phenethyl, α-methylbenzyl, CH_2CH_
2CH_2N(CH_3)_2, substituted phenyl (however,
Substituted phenyl refers to a phenyl group that may be optionally substituted with the following substituents; halogen atom, C_1
-C_4 alkyl, C_1-C_3 alkoxy, C_1
-C_2 alkylamino, N(CH_3)_2, CO_
2-(C_1-C_2 alkyl), C_1-C_2 alkylcarbonyl, C_1-C_2 haloalkyl or C
_1-C_2 haloalkyloxy) or substituted benzyl (however, substituted benzyl refers to a benzyl group that may be optionally substituted with the following substituents; halogen atom, C_1-C_4 alkyl, C_1-C_3 alkoxy, C_1-C_2 Alkylamino, N(CH_3)_2
, C_1-C_2 alkylcarbonyl, NHCOCF_
3, CO_2-(C_1-C_2 alkyl), SO_2
CH_3, SO_2CF_3, C_1-C_2 haloalkyl or C_1-C_2 haloalkyloxy). ], ▲ Numerical formulas, chemical formulas, tables, etc. ▼ [However, n represents an integer from 1 to 4, and R15 represents the same meaning as above. ], SC
H_2-Y-R16 (However, Y has the same meaning as above, and R16 is a hydrogen atom, C_1-C_5 alkyl, CH_
2CN, CO-(C_1-C_4)alkyl, COCH
_2Cl or CON(CH_3)_2 is shown. ] SCH_2-Y-CH(R14)CO_2R15 [However, Y, R14, and R15 represent the same meanings as above. ], ▲Mathematical formulas, chemical formulas, tables, etc.▼[However, Y, n, and R15 represent the same meanings as above. ], SCH_2-Y-P(O)(OR17)_2 [However, Y
represents the same meaning as above, R17 is a hydrogen atom, C_1
-C_4 alkyl or R' represents benzyl. ] or SCH_2-Y-P(S)(OR17)_2 [However, Y
, R17 represents the same meaning as above. ] is shown. ] However, when A and E form a ring, the formula (
II) or formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, G, R, R' represent the same meanings as above, and J is a hydrogen atom, C_1-C_4 alkyl, CH_2OH, C
H_2Cl, C_2-C_4 alkenyl, C_3-C_
4 alkynyl, CH_2CH, CH_2CONH_2 or benzyl. ] A triazinedione derivative represented by. (2) A herbicide containing the triazinedione derivative according to claim (1) as an active ingredient.