JPH03287585A - Uracil derivative and noxious life controlling agent - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (X is O or S; Y is H, halogen, etc.; Rf is 1-6C haloalkyl; R is H, alkali metal, etc.; Het is 5-membered hetero- ring, 6-membered hetero-ring, etc., containing N, O, etc.). EXAMPLE:3-(5-Neopentyl-1,3,4-thiadiazol-2-yl)-6-trifluoromethyl-2,4(1H ,3H)- pyrimidinedione. USE:A herbicide and vermin-controlling agent. It has high selectivity to important crops and exhibits high herbicidal effect against weeds. Vermin can be controlled at an extremely low concentration causing little influence on mammals, etc. PREPARATION:The objective compound of formula I wherein R is other than alkali or alkaline-earth metal can be produced by reacting a compound of formula II with CH3CO2NH4 or a compound of formula R-NH2 in the presence of acetic acid and reacting the resultant compound of formula III with a compound of formula CXCl2 in the presence of a base such as pyridine.

Description

[Detailed description of the invention] [Industrial application field]

The present invention relates to a novel uracil derivative and a pest control agent containing the derivative as an effective acid component.
In the present invention, pest control agents mainly mean herbicides and pest control agents.

[Conventional technology and section! ! ]

As a known document regarding uracil compounds, U.S. Patent No. 3
．． No. 580,913, No. 3,869,457, and No. 3,981,715 describe the herbicidal action of uracil derivatives in which the 3-position of the uracil ring is substituted with alkyl, phenyl, etc. . However, there is no known uracil derivative in which the 3-position of the uracil ring of the compound of the present invention is substituted with a heterocycle.

[Means to solve the problem]

In view of this situation, the present inventors continued research to develop an excellent pest control agent, and as a result, (hereinafter referred to as blank) Formula (I):

[In the formula, X represents an oxygen atom or a sulfur atom, Y is a hydrogen atom, a halogen atom, C, -C, an alkyl group, C1 to C4
Haloalkyl group % C1-C4 hydroxyalkyl group, C
Z-C4 alkoxyalkyl group, 02-C4 alkylthioalkyl group, cyano group, thiocyanate group or nitro group, R, represents C1-Ch haloalkyl group,
R is a hydrogen atom, an alkali metal, an alkaline earth metal, C1
-04 alkyl group, C! ~c4 alkenyl group, C, ~c
4 alkynyl group, CI-c4 haloalkyl group, cz~C
4 alkoxyalkyl group, pormol group, cg~C-alkylcarbonyl group, CZ~C, alkoxycarbonyl group, C1~C, alkoxycarbonylalkyl group, C1~
c6 represents a cyanoalkyl group, benzyl group or phenyl group, and Net represents a 5-membered heterocycle, 6-membered heterocycle or fused heterocycle containing at least one nitrogen atom, oxygen atom or sulfur atom. We have found a uracil derivative (hereinafter referred to as the compound of the present invention) represented by the following formula. Examples of Het include a heterocycle represented by the following formula. (R1 is hydrogen atom, halogen atom, C1-C11 alkyl L C3-C, cycloalkyl group, C2-C, haloalkyl group, C3-C, alkenyl group, cs-C11 alkynyl group, 03-C6 cycloalkyl (c+ - C4)
Alkyl group, 01-C, alkoxy (C, ~C,) alkyl group, C3-C6 haloalkyloxy (C+-C4)
Alkyl group, C1-C, haloalkylthio group, C1-C
h Haloalkylsulfinyl L c, ~C1Cl alkylsulfonyl group, cyano group, substituted phenyl group (as a substituent, hydrogen atom, halogen atom, C1-C4 alkyl group, C1-C4 alkoxy group, CI-Ca alkoxycarbonyl group, C1-C4 haloalkyl group, CI""'C4
Haloalkoxy group, C2-C4 alkylthio group, CI~
C4 haloalkylthio group, C, -C, alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, c+~C
4-alkoxycarbonyl group, carboxyl group, amino group, CI"" Ca alkylamino group, C, -C, dialkylamino group, cyano group, phenyl group, benzyl group, methylenedioxy group, haromethylenedioxy group, nitro group , substituted benzyl group (the substituent has the same meaning as substituted phenyl group), substituted phenoxy (C+ to C
4) Alkyl group (represents the same meaning as a substituted phenyl group as a substituent), substituted phenylthio (C+ to C4) alkyl group (represents the same meaning as a substituted phenyl group as a substituent), substituted benzyloxy (CI-C4) alkyl group (the substituent has the same meaning as the substituted phenyl group), substituted benzylthio (CI-C4) alkyl group (
As a substituent, it represents the same meaning as a substituted phenyl group,
), Cl-C1 alkylti t&, C1-C, alkylsulfonyl l! cr~C6 alkylsulfinyl group, C
O! R7 (R7 represents a hydrogen atom, C8 to C, an alkyl group, a phenyl group, a benzyl group), C0N(R8)R
9 (R8 and R9 are each independently a hydrogen atom, CI-
Cs alkyl group, CI-CzCm-kylsulfonyl group, phenyl group, benzyl group, Cm-C-alkenyl group, C3
~Ch represents an alkynyl group, and R8 and R9 may form a 3- to 6-membered ring composed of any atoms among carbon atoms, oxygen atoms, and sulfur atoms. ), So! N(R8)R9 (R8, R9 represent the same meanings as above), N(R8)R9 (R8, R9 represent the same meanings as above) or 0RII (R11
・Hydrogen atom, CI~C, alkyl group, C3~Cs alkenyl group, C3~C, alkynyl group, C1~C, haloalkyl group, phenyl group, benzyl group, CHzCOzR
12 (R12 represents a hydrogen atom' or a C1-CI alkyl group) or CH2C0N(R8)R9 (R8 and R9 represent the same meanings as above). R2 represents a hydrogen atom, a halogen atom, a C1-C, alkyl group, a C+-C, haloalkyl group, or a C3-C, alkoxy group. R3 is a hydrogen atom, a halogen atom, C~
Ch alkyl group, C1-C6 haloalkyl group or C1
~C represents a haloalkoxy group. R4 and R5 are each independently a hydrogen atom, a halogen atom, CI""C@alkyl group, C3-C8 alkenyl arcs-C, alkynyl%, Cl-Cs haloalkyl group, C1-Ch alkoxy group, or N(R8)R9 (R8 and R9 represent the same meanings as above). R6 is C, -C, alkyl group, C
1-C. Alkenyl group, C3-C6 alkynyl group or C1-C
h represents a haloalkyl group; n represents an integer from 1 to 3; ] The compound of the present invention can be used in both soil treatment and foliage treatment, such as Physalis japonica, Datura japonica, Japanese thornweed, American golden deer, mulva morning glory, japonica, Japanese violet, Japanese fir tree, Japanese fir tree, pigweed, sunflower, Japanese leafminer, and Japanese staghorn. , Japanese wildflower, Japanese daisy,
Broad-leaved weeds such as dogberry, field mustard, shepherd's purse, Japanese knotweed, freckles, purslane, whiteweed, koakaza, broomweed, chickweed, giant dogweed, daywort, hotokenoza, commonweed, konisikisou, japonica, commonweed, madder, swamp, black-and-white, black-and-white weed, etc. Weeds of the grass family, such as wild trumpet gum, japonica grass, johnson grass, golden grass, grasshopper, oat, grasshopper, foxtail grass, and grass gnome;
It has a high weed power against various paddy field weeds such as Cyperaceae such as Cyperaceae, Helaomodaka, Omodaka, Urikawa, Tamagayatsuri, Mizugayatsu, Hotarui, Kurogwai, Azena, Konagi, Hirumushiguchi, Kikashigusa, and Japanese millet. It can also be safely used for important crops such as wheat, corn, barley, soybeans, rice, cotton, peanuts, beets, and turgid gum. The compounds of the present invention are characterized by having higher selectivity for important crops than conventional herbicides and by exhibiting high herbicidal effects against a wide variety of weeds. Furthermore, the compounds of the present invention exhibit efficacy against various harmful pests at extremely low drug concentrations. The pests include, for example,
Agricultural pests such as black leafhopper, brown planthopper, green peach aphid, Japanese ladybug, fall armyworm, and diamondback moth; spider mites such as Japanese spider mite, Japanese spider mite, and Kanzawa spider mite; sanitary pests such as Culex mosquito, house fly, German cockroach, ants, fleas, and white-winged spider mite; Examples include grain storage pests such as the brown weevil, brown weevil, and striped mealybug, household pests such as termites, and livestock pests such as mites, fleas, and stag beetles. That is, the compounds of the present invention can effectively control insect pests of the orders Orthoptera, Hemiptera, Lepidoptera, Coleoptera, Hymenoptera, Diptera, Termites, and Acarinae at low concentrations. On the other hand, the compounds of the present invention have almost no adverse effects on mammals, fish, and beneficial insects. In addition, when the substituent R is a hydrogen atom, the compound of the present invention represented by formula (I) can have tautomers as shown below, and the compound of the present invention has all of these tautomers. It includes the form. (Hereinafter, blank space) The compound of the present invention is a novel uracil derivative having a heterocycle at the 3-position. Synthesis methods include, for example, comprehensive heterocyclic chemistry,
Volume, 57 pages, 1984 (A, R, Katritzk
y, et al, + Comprehensive)
1eterocyclic chemistry, L
The uracil bone nucleus can be prepared by referring to the synthesis method described in J.D., 57 (1984) and the like. In addition, one of the starting materials, 3-amino-4,4,4-
) Rifluorocrotonic acid esters are described in Journal of Heterocyclic Chemistry, Vol. 9, 51.
3 pages, 1972 (A.W. Lutz, etal.
J, Heterocycle, Chew.
L (3), 513 (1972)) etc. can be used as a reference. The compounds of the present invention can be obtained by the synthetic routes shown in schemes (1) to (5), including the methods described above. Rf, YSHet, and R in scheme (1) have the same meanings as above. Hal is a halogen atom, R21 is
For example, lower alkyl group, benzyl group, phenyl group, C
)12cO, )l, etc., acid represents para-toluenesulfonic acid, concentrated sulfuric acid, etc., and base is,
For example, sodium hydride, sodium methoxide,
Represents potassium carbonate, etc. Rt, X, YSHet, R, in scheme (2)
HaIl represents the same meaning as above. R21 and R22 each independently represent, for example, a lower alkyl group, a benzyl group, a phenyl group, CHtC (hH, etc.), and base
represents, for example, sodium hydride, sodium methoxide, potassium carbonate, etc. Scheme (1) cid Scheme (2) Scheme (4) Scheme (3) Scheme (5) i (However, Y represents a halogen atom or a nitro group) If vP<. Rt , X % Y , Het , R in scheme (3)
represents the same meaning as above, R21 and R22 each independently represent, for example, a lower alkyl group, benzyl group, phenyl group, CH, CO□H, etc., and base represents, for example, sodium hydride, sodium methoxide. , potassium carbonate, sodium hydroxide, etc. In scheme (4), Rr s
Represents sodium hydride, sodium methoxide, potassium carbonate, pyridine, etc. R1, X, Y, and Het SR in scheme (5) represent the same meanings as above. Examples of the halogenating agent include fluorine, chlorine, bromine, iodine, and sulfuryl chloride, and examples of the nitrating agent include nitric acid, copper nitrate,
Represents nitrate, isopropyl, etc. When it becomes necessary to purify the compound of the present invention, recrystallization,
It can be separated and purified by any purification method such as column chromatography. In addition, in the case of a compound having an asymmetric carbon among the compounds included in the present invention, optically active compound (+) form and (-) form are included. Furthermore, when configurational isomers exist, cis and trans isomers are included. Examples of synthesis of the compounds and intermediates of the present invention will be specifically described below, but the present invention is not limited thereto. Synthesis of 5-neopentyl-1,3,4-thiadiazole Thiosemicarbazide 20g, t-butyl acetic acid 25,5
35 g of phosphorus oxychloride was added dropwise over 1 hour to a mixture of 7011N of dioxane while stirring under reflux. When the reaction was completed and hydrogen chloride gas was no longer generated, the reaction mixture was taken out by decantation, and 50- of water was added. was added, and the pH was adjusted to 10 with sodium hydroxide pellets under water cooling. The obtained solid was washed with water and then recrystallized from methanol to obtain 18.8 g of the target compound as light purple crystals. Melting point 260-261°C MS (m/Z) 171 (M”), 156
(M CH3)” 15 11 21 2-ethoxycarbonylamino-5-neopentyl-1
, 3,4-thiadiazole base two main members 3'-(5-neopentyl-1,3,4-thiadiazol-2-yl)-6-trifluoromethyl-2,4(I
Synthesis of H,3H)-pyrimidinedione (compound of the present invention)
Nα1) 5-neopentyl-1,3,4-thiadiazole 5g, pyridine 50mj! into the mixture, under water cooling,
The reaction mixture to which 16 g of chloroformic acid ethyl ester was added dropwise was stirred under reflux for 3 hours. After the reaction was completed, pyridine was distilled off, and the mixture was acidified with hydrochloric acid while cooling with water. The obtained solid was washed with water, passed through the mouth, and dried to obtain the target compound 5.
57 g was obtained as pale yellow royal crystals. Melting point 166-170'C'HNMR (CDCj!s) δ; 1.05 (98, s), 1.33 (3H, t
, J=7Hz), 2.88 (2B, s). 4.28 (2H, Q, J-7H2) MS (m/Z) 243 (M”), 22B
(M CH3)”, 1873-amino-4,4,
To a mixture of 1 g of ethyl 4-trifluorocrotonate and 5 ml of dimethylformamide, 230 μl of sodium hydride (oil, purity 55%) was gradually added at room temperature. After stirring for 1 hour after addition, 2-ethoxycarbonylamino-
5-neopentyl-1,3,4-thiadiazole 1,3
After the reaction was completed, the mixture was poured into water and acidified with hydrochloric acid while cooling with water. This was extracted with ethyl acetate and washed with water.
Dry over anhydrous sodium sulfate, evaporate the solvent, wash the resulting crude with isopropyl ether and n-hexane,
680 ml of the target compound was obtained as ocher crystals. Melting point 248°C decomposition'HNMR (CDCj!s +DMSO-da) δ;
1.06 (9H, s), 3.00 (2H, s),
6.06 (IH, s) M S (m/Z) 27
8(M-tertBu+H)", 141,51
21 3-(5-neopentyl-1,3,4-thiadiazol-2-yl)-1-methyl-6-trifluoromethyl-
Synthesis of 2,4(1)(,3H)-pyrimidinedione Ifi
(Compound of the present invention Nα2) 3-(5-neopentyl-1
, 3,4-thiadiazol-2-yl)-6-)lifluoromethyl-2,4(IH,3H)-pyridinedione 470■, dimethylformad 3-1 potassium carbonate 2
1 g of methyl iodide was added to the mixture of Step 30 at room temperature and stirred for 28 hours. After completion of the reaction, the mixture was poured into water, extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, then anhydrous. Dry with sodium sulfate. After evaporation of the solvent, the obtained crude liquid was washed with isopropyl ether and n-hexane and dried to obtain the target compound 270 as ocher crystals. Melting point 189-190°C 'HNMR (CDCj!s) δ; 1.08 (9H, s), 3.03 (2H, s),
3.52 (38, br s). 6.38 (LH, s) MS (m/Z) 333 (M - CH3)'',
292, 141 actual offense 121 3-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-6-trifluoromethyl 2.4 (IH
,3H)-pyrimidinedione (compound of the present invention, 3) To a solution of 0.78 g of sodium hydride (purity 55%) in 30 ffll of dimethylformamide, 1.59 g of dimethylformamide was added under stirring under cooling with water. 10ffll solution was added dropwise. After stirring under water cooling until the generation of hydrogen gas was finished, a solution of 3.24 g of 2,3-dichloro-5-trifluoromethylpyridine in 74,110 ml of dimethylform was added dropwise. After further stirring for 4 hours at room temperature, the reaction mixture was poured into ice water and extracted three times with 50 liters of ethyl ether. After washing three times with water and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to remove the 2-ethoxycarbonylated 3-chloro-5-
0.93 g of trifluoromethylpyridine was obtained. To a solution of 0.22 g of sodium hydride (purity 55%) in 74110 ml of dimethylform, ethyl 3
-amino-4,4,4-)rifluorocrotona) 0
．． 92 g was added dropwise. After warming to room temperature and stirring for 15 minutes, return to water cooling and remove 2-ethoxycarponylua.
-Chloro-5-trifluoromethylpyridine 0.93
g was added dropwise. After stirring at 100"C for 3 hours, dimethylformamide was distilled off under reduced pressure, and the residue was dissolved in 100 s of water. After washing this aqueous solution with diethyl ether, it was dissolved in a mixture of 50 g of water and 20 l of concentrated hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain 0.20 g of the target compound. Melting point: i9o, o~191.0°C'H -NMR (CDi, +CD30D) δ; 6.1
0(1)1. s), 8.12 (IH, s), 8.61 (
IH, s) 1 Chloro-pyridin-3-yl-6-trifluoromethyl-2,4(IH, 3H)-pyri-based dinedione (compound of the present invention, 4) Sodium To a solution of 0.43 g of methoxide in dimethylformamide 10111 was added 1.4 ethyl 3-trifluoro(4,4.4-trifluorocrotonate) under stirring under water cooling.
6 g was added dropwise. After stirring at room temperature for 15 minutes, the mixture was returned to cooling with water, and 1.53 g of 3-ethoxycarbonylamino-6-chloropyridine was added dropwise. After stirring at 130°C for 3 hours, dimethylformamide was distilled off under reduced pressure, and the residue was dissolved in 100w+f of water. After washing this aqueous solution with diethyl ether, it was added to a mixed solution of 50 g of water and 20I111 of concentrated hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed with water, dried, and the solvent was distilled off under reduced pressure to obtain 1.10 g of the desired product. Melting point: 174.0-175.0°C 'HNMR (CDCjl!s +DMSOd-h) δ;
6.12 (IH, s), 7.30-7.70 (2Fl
, m), 8.27 (18, d. J・3.0Hz) Next, the numbers and structures of the compounds that were bottomed out according to the above examples or schemes are listed in Table 1, and the physical properties of those compounds are Properties are shown in Table 2. (Hereinafter, blank space) Table 1 CH. Table ■ (Continued) Table 1 (Continued) Compound number Structural formula % Formula %) Table 2 (I) Invention compound'H-NMRδ (ppm) [Solvent] Physical properties 1.06 (9B, s), 3.00 (2H, s). 6.06 (1B, s) (CDCl2 s + DMSO-di) mp=
248℃ decomposition 1.08 (9) 1. s), 3.03 (2L
s). 3.52 (3tl, br s), 6.38 (IH, s)
(CDCj!3) 5p=189~190
°C6,10 (1B, s), 8.12 (IH, s),
8.61 (IH, s) (CDCl2 s + CD co00) mp=190.0~191.06.12
(18,s), 7.30-7.70(2H,,+w
). 8.27 (18,d, J=3.0Hz) (CDC1
, + [1M5Q-d, ) Kano = 174.0-175
．． 0 °C6, 10 (IH, s), 7.34 (IH
, d, J=7.0Hz). 7.58 (IH, d, J=7.0Hz) (CDCl2
s+DMSO-da)mp=123.0-12
6.0 ℃6 3.60 (3H, s), 6.08 (
11 (, s), 6.17 (IH, d, J = 2 Hz), 7
．． 46 (IH, d, J=211z), 9.60 (IH,
br s) (DMSO-dh) sap
=108-113℃7 3.50(3H,s)
, 3.61 (3H, s), 6.17 (IH, d, J=2
Hz), 6.28 (IH, s), 7.48 (IH, d,
J=2)1z) (CDCj2s) Glassy oil 8 1.45 (9H, S), 6.07 (IH
,s)(CDCf3+DMSO-di)mp=
275-277°C Next, examples of compounds included in the present invention are shown in Tables 3 to 15, including the aforementioned compounds 1 to 8, respectively, but the present invention is not limited thereto. (Below, blank space) f CF3 Fs CF3 h Fs CF3 Fs Fs CF3 CF3 Fa CF3 Table 1 (continued) CF. Fs ■ CHgC(CHs) zcJs CHzC(CgHs)s I CH3 C寞Is C11(CHs)g CBsCIIzCHs C(CHs)s C(CH3)3 C(C1ts)s C(CJs)gcHs CHzC(CH3)s C HgC( CBs)s CHxC(CHs)s CH-rich C (C18%)tc)Is CF3 CF. C.F. CF .Fs CF. HzCFs CHgC(CHs)zcHzP GHzC(CHs) ICHICjI CHIC(CHI)IcH! Summer FI CF. CF. CF3 FI CF. h CHzC(CHgF) zcHs CHz OcH3 CH(CH3)OCH3 CH(CHs)OCiHs CHzOCFs CHzOC (CH3)s HxCJs CHzCHzSCJs CHzCHzOCJs SCH. SC, H. Table 3 (continued) Table 3 (continued) f Fs CF3 CF3 CF3 CF3 Fs CF. CF3 h Fs CF3 Fs h 1 SC) l( CH3)! SO□ C28% 0CJs OgCHs CO□C(CHs)3 CHzC(hCH+ CHxCOC(C1h) 3 CON (CHs) z CHgCONHC(CHs) 5 CHzCON(CHs) * C0NCONH30I CH3COO(CH 8) □NHC (CIsu3 f 1 CF3 CF3 CF. H CF3 CF. CF3 Fi CF3 CF3 Fi Fi CF. CF3 CF. S ) 2 0CHgCO*CHs CHzC(CHs) 5 CHIC(CH3) 5 CHzC(CHi)s CHzC(CH8)s C(CHs)s Table 3 (continued) Table 4 FsCFI hCh CF3CH2 CF 3CH2 CF3 h CF3 CF3 hCF3 (Hereafter, blank space) CHzC(C)Iz')s C(CH3)3 GHzC(CH+) 3 C(CHz)s F2CF3 HICF3 C(CF3)3 C(CH3)3 C(CH3)3 GHzC(CB,) s CF3 Ft CF. CF3 CF. F2 CF3 FI CF. CF. CF. (CJs) zc) I. C31C(CH3)3 CHIC(CH3) 3 CHzC(CHs) 3 CIbC(CJs) zc)lz FI CFs CF3 CF3 CF3 CF3 h CF3 FI CF3 Fff CF3 CFs CF3 C.F. CF3 (continued) Table (continued) 1 f CHzC(CHs) zczHs CHlC(C!I(S). FI CF. CF. CF3 CFs CFs CF3 1 CElzC)I=CHz I F2CF3 CF. C(CHs)zcHzF C(CHs)zcHzcl C(CHs)tcmiCH HCHzC(CHs) zcmiCI Hct+zcmiCH CFs h CF3 CF3 HICFI CHzC(CHs) zcIhF CH zC(CHs) gcHzc 1 CLC(CHs)tcIhl continued) 1 f CHzC(CHJ) ICH3 CH, OCH3 CH((J 3) OCRa CH(CHz)OCJs CH!0CF3 CHzOC(CL)s CH,C,H. CHzCHgSCil(s CHzCHzOCil(s CHs cans CF3 CF3 CF3 CF3 CF3 CF3 CF3 CF3 CF3 CF. CF3 CF. CF3 Table 4 (continued) 1 SCH(CH3)! SO□C,H5 oczns CO2C)13 CO2C(CH:l) 3 GHzC(hcHz CJlgCOC(CHz) 3 CON( CHz)z CHtCONHCCCH3)3 CToCON(CH3)z CONHSO,CH3 5OJ(CH8h SO!NHC(CHz)s CFs CF3 CF3 h CF3 CF3 CFs CFs C+S CFs CFs CF3 CF3 CFs CF h CF3 CF3 CF3 CF3 CFs CFs h CF3 CFs h Continued) Table 4 (continued) N(CHs)z N(SOzCH3)CgHs N (CO(CHs z) z N)Ic(CHz) s NH. H F1 ctts OCH*C(CHs)s OCR Snow CO, CH. CHxC(Clh)a CHzC(CHs)a CHzC(CI+)s C) Igc(CHs) 5 C(CHs)s f CF3CF! H CF, CF, II CF, CH, H CF, CO, H CF, H CFs H CFs H CFs CI CFs Br CF3 Br 1 C) Igc(CH3)s C(CH3)3 CHgC(CHs)s C(CH3)I FzCFs thCFs CCCF3)s C(CH3)3 C(CH3)3 GHzC(CHs ) 3 (below, margin) Table (continued) CF3 CHxC(CHz) zctls CHa C,1(S CH(CH3) I CHzCI(tcHz C(CHs)s C(CHs)s C(CHs) x C(CIHs) ) 1cH3 CHIC(CHI)I CI(zc(CHa) s CO-rich C(CH3)3 CF3 CF3 CFs C(CH3)IC3CH CHzC(CHz)zcmiCH Cl1. C Mi CH CFI CFI CF. CFs CFs Pm CF3 CFs CFs CF3 CFs CF. C.F. C.F. C.F. C.F. C.F. CFs CFs CF. C.F. C.F. C.F. CFs continued) Table 5 (continued) 1 CH□CH=CH. l cpgcp. CFs C(CN3) gcHJ C(CHs)zcHscf CByoCFs CHgc(CL) xcHzF CHgC(CHs) zcHtc I CHgC(CHs) zcHxl CFs CF3 CFs CFs CFs CF. C.F. CFs CF. CFI CF3 CHgC(CHzF) zcHs CIhOCold CB(CHs)OCHs CH(C1h)OCJs C11jOCFkoCHzOC(CHs)s CHzChHs CHxCHxSCJs CBgCIIzOCJi CH3 5c, i. Continued) 1 SCH(C1h)z SOgCzHs OCzHs C(hCHs COgC(CHs)s CIhCOzCHz CHzCOC(C1h)s CON(C)Is)z CI(zcONllc(CHs) 5 CHtCON (CHs) C0N) IsO□CO. 5OzN(CHs) So! NHC(CH3)3CF. C.F. CFI CF. CFI CFI CF3 CFs CF3 CF3 CF. C.F. CF3 CFI CF. Table 5 (continued) 1 a N(CHs)x N (SO□C1(:+)CJs N(CI(CHs)x)z NHC(CHi)s NH. tl H CR3 0CH*C(CHs)s OCHzCOzCHa CHgC(C)Is) CHgC(CHs)s CHzC(CHs) s CHIC(CH3)3 C(CHs)s Table 5 (continued) f CF, CF. C.P., C.F. FsCHg CF, CII. C.F. CFs CFs CFs CF. CFs Br Br l 1 CHgC(C)Is)s C(CTo)3 CHgC(CHs)i C(CH3)3 CF, CF. CI(ICF3 C(CF3)3 C(CH3)3 C(CHs)s CIhC(CHs)s (Hereafter, margin) f F2 CF3 CF3 CFs CF3 CF3 CFs CF3 CF. CF3 CF3 CF3 f CFs CFs Table (continued) 1 HC31C(CH3)zcJs HCHzC(CzHs) 3 F3 CF. F. CF. CF. 6th Table I CI3 Js CH(CHs)z CHzC)IxCHa C(CH3)3 C(CH3)3 C(C)13)3 C(CJS)2CH3 GHzC(CH8) x CHIC(CH3) :+ CH,C(CH ,). CHzC(C!Hs) 2CH3 Table 6 (continued) CHzCH=CHg 1 hCFI CFs C(CH,) ZCH2F C(CH3) zcHzc l CH,CF3 CH2C(C)13) 2CH2F C1hC(CHs) zcH zc 1 CIhC(CH3 ) zcHzl CF. C.F. FICF. hCF. C.F. C.F. C.F. C.F. C.F. Table (continued) Table 6 (continued) 1 CHxC(CToF) zcHs CHzOCl(s CM(CH3)OCI(3 CH(CIsu0(,Is CHgOCFs CHtOC(CHs)s CHIC6H5 CHzCIIzSCbHs CHzCHgO CaHs cns SC, H. CF. CF. CF3 CF3 CFs CF. CFs CF3 CF. CF. CF. CF. CF. 5CH(CH3)! s)s CON(CHs)g CIICONIIC(CH3) 5 CHiCON(CHs)z CONHSO*CHs SOJ(CHs)z SOJHC(CH3)3 (continued) 1 a N(CH3)z N(S(hclh)CJs N(CH(CHz)z)z NHC (CH3)! NH. CF, CF. CF, CH2 hCHz CF3 CF. CF3 CF3 CF3 CF. z CFICF. CH, CF. C(CFs)s C(CH3)3 C(CH3)3 C8IC(CH3) 3 Margin) f Ch Fs CF こFs CF. CF. Fs Ps CF. CF. CF. Fs CF. CF. CF. CF. CF3 CF. Table 7 I II CI(CHs)z C(CHs)s C(CHx)s C(CJi)zcHs CHgC(CHs)s CHzC(CHs)xczHs CHgC(CzHs) zcHs Table 8 CHa CI (CHs) * C (CHs)s C (CHs) C (CJs) zcHs CHgC (CHs) 5 CHzC (C1h)zcxHs CHzC (CJs) 1CH3 Table (continued) F2 C(CH3)2C3 〇〇CF3 Fs CF3 CF. CF. ( CHa)s C(CHz)a Table 8 (continued) f 1 2 CF3 Ch CF. CF3 F2 CF3 CF. CF3 CF3 Fs C(CJs)3 Fs CFICF. CHzC(CH:+)z C82C(CH3)s C(CH3)3 GHzC(CH:+)3 C11, C(CH3)i CHzC(CHa)3 C(CHs)a CFa CFa CFa CFa CFa CFa CFa CFa CFa h f CF3 CF3 CFa CF3 CFa CFa CF3 CFa CFa Table 9 CH3 CB(CHs)* C(CHs)a C(CHs)s C(CJs)gcHs CHzc(CHs)s CHzC(CHs)xczHs CHzC(Cx Hs) xcHs 10 Table I CHa Cll(C)Is)x C(CHs)+ (:(CH3)a C(CJs) *CHs CHgC(CH3)s CHgC(C11a) gcgHs CH*C(Cz)Is) ICH3 CFkoCFa CF3 CFa CFa CFa CF3 CF3 CF3 CF3 CP. C.F. CF3 CF3 CF. Fj CF. CF3 CF3 CF. Table 9 (continued) C(CzHs)s CF. CF寞CF. CHzC(CHs)s CHgC(CHs)s C(CHs)s CHyoC(CHa) 5 CHzC(CHs)s CHoC(CH3)5 C(CHs)s Table 10 (continued) C(CzHs) 3 CF3 CF, CF. CToC(CHs)s CHIC(CH3)3 C(CI(3)3 CJC(CH3)z CHIC(CH3)3 CHgC(CHl)z C(C)Is)z Rf・ CF3 Fs Fs CF3 FI FS Fs CF3 Fs Table 11 Table 11 (continued) Rf 1 2 I C)1m CH(CI(s)z C(CHs)s C(C)Is)s C(CzHs)zcuz C)lzc(CHs) s CHgC(CHs) *CzHs CLC (CzHs)zcHs Fs Fs CF. CF3 Fi Fi CF3 CF3 CF3 CF3 CF3 CF3 C (CJS) S LH PGCTS C) BC (CH3) 5 Chic (CH3) 5c (CH3) I GHZC (CH3) Z CHZC (CHS) A CHZC (, CI (CI) 5 C ( CHs)s Table 12 (Continued X 1 A! I 2 3 A. Continued> R. ＾1 2 3 4 Table 1 (Continued) Table 1 (Continued) A. ＾= 3 4 (Hereafter, margin) Table 3 (Continued) 1 2 3 4 (Hereafter, margin) 1st Table (below, margin) Table (continued) f et Table 5 f et Table 5 (continued) f et Table 1 (continued) f et Table 5 (continued) f et Q1 in Table 15 above ~Q5 1 is a group represented by the following structural formula: When applying the compound of the present invention as a pest control agent, it is generally used in a suitable carrier, such as a solid such as clay, talc, bentonite, diatomaceous earth, or white carbon. Carrier or water, alcohols (isopropanol, butanol, benzyl alcohol, furfuryl alcohol, etc.),
Aromatic hydrocarbons (toluene, xylene, etc.), ethers (anisole, etc.), ketones (cyclohexanone, isophorone, etc.), esters (butyl acetate, etc.), acid amides (N-methylpyrrolidone, etc.) or carbonized halides Can be applied in combination with a liquid carrier such as hydrogen (chlorobenzene, etc.), and can be used as a surfactant, emulsifier, dispersant, penetrant, spreading agent, thickener, antifreeze agent, and anti-caking agent if desired. By adding additives, stabilizers, etc., the composition can be put to practical use in any desired dosage form such as liquid, emulsion, wettable powder, dry flowable, flowable, powder, or granule. In addition, the compound of the present invention may be used with various herbicides, various insecticides, fungicides, plant growth regulators,
It may also be used in combination with a synergist. As for the type of herbicide to be mixed, for example, Farm Che+*1ca
lsHandbook) 1989 edition. The amount of this application varies depending on the application situation, application time, application method, cultivated crop, etc., but in general, the amount of active ingredient is 0.05 to 0.05 per hectare (ha).
Approximately 10 kg 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. L gold member Wettable powder Compound of the present invention Nαl ・・・・・・50 parts Siegrite PFP ・・・・・・43 parts (Kaolin-based Kreichi-Dikrite Kogyo Co., Ltd. product) Name) Tsurupol 5050 ・・・・・・・・・ 2 parts (
Anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Lunox 100OC...3 parts (anionic surfactant: Toho Chemical Industry Co., Ltd. trade name) Carplex #80 (solid anti-caking agent)... 2 parts or more (white carbon: trade name of Shionogi & Co., Ltd.) are uniformly mixed and pulverized to make a wettable powder. Sockeye salmon emulsion Compound of the present invention N111 3
Part xylene 76 parts Isophorone 15 parts Tsurupol 3005X 6 parts (Nonionic surfactant and anionic surfactant Mixture with agent: Toho Chemical Industry Co., Ltd. (trade name) The above ingredients are mixed uniformly to form an emulsion. L Gold amount 1 Flowable agent Inventive compound 11kL8 ・・・・・・・・・3
5 parts Ageli Seal S-711 8 parts (nonionic surfactant: Kao Corporation trade name) Lunox 100OC 0.5 part (anionic Surfactant: Toho Chemical Co., Ltd. (trade name) 1% Rhodobol water 2 (1 (thickener: Lone-Boulin brand)) Ethylene glycol (antifreeze agent)...・8 parts water
...... 28.5 parts or more are mixed uniformly to form a flowable agent. Granules of the present invention Compound Shame 8 ・・・・・・・・・0.1 part Bentonite ・・・・・・55.0 parts Talc ・・・・・・44.9 parts After uniformly mixing and pulverizing the above, a small amount of water is added and the mixture is stirred and kneaded, granulated using an extrusion type granulator, and dried to form granules. jlliu - Granular hydrating agent (dry flowable agent) Compound of the present invention NIILl 75 parts Isopane? 411 ......1 part (anionic surfactant: Clarei Soprene Chemical Co., Ltd. trade name) Vanillex N ......5 parts (anionic surfactant: Sumikokusaku Valve Co., Ltd. (trade name) Carplex #80 ・・・・・・・・・10 parts or more (white carbon: Shionogi & Co., Ltd. trade name) are uniformly mixed and pulverized to form a dry flowable agent. do. When using, the above-mentioned hydrating powders, emulsions, dry flowable preparations, and flowable preparations are diluted 50 to 1000 times with water so that the active ingredient is 0.00% per hectare (ha). OO1~2
Spread it to make a total of kg. Next, the usefulness of the compound of the present invention as a pest control agent will be specifically explained in the following test examples. tUt21 Herbicidal effect test line by foliage treatment 15C1,
Put sterilized diluvial soil into a plastic box with a width of 22C11 and a depth of 6C1+1, and grow dogfish, leafminer,
Seeds of dogberry, corn, wheat, and soybean were sown in spots, and covered with soil of approximately IC111. When each plant reached the 2-3 leaf stage, the active ingredient was uniformly sprayed onto the stems and leaves so that the amount of the active ingredient was at a predetermined ratio. The chemical solution used for spraying was prepared appropriately according to the formulation example described above, diluted with water, and sprayed using a small sprayer over the entire foliage of various weeds and crops. Chemical spraying 4
After a week, the herbicidal effects on various weeds and the chemical damage to various crops were investigated according to the following criteria. Results first
It is shown in Table 6. Judgment Criterion 5: Weed killing rate 90% or more (almost complete death) 4.
...Weed killing rate 70-90% 3...Weed killing rate 40-puO% 2...Weed killing rate 20-40% 1...Weed killing rate 5-20% 0...Weed killing rate 5% or less However, the above herbicide rate was determined by the following formula by determining the weight of above-ground plants in the chemical-treated area and the weight of above-ground plants in the untreated area. Table 16 3.2 6.3 12.5 5000 5000 5000 1.6 5 5 5 0 0 4 3.2 5 5 5 0 0 5 6.3 5 5 5 0 1 5 3.2 6.3 5000 After sowing 5,000 g of soybean seeds and covering with soil of about 5,000 g,
The amount of active ingredient was uniformly spread over the soil surface at a predetermined ratio. The chemical solution used for spraying was a wettable powder, an emulsion, a dry flowable powder, or a flowable powder prepared as appropriate according to the formulation example described above, diluted with water, and sprayed over the entire surface with a small sprayer. Three weeks after spraying the chemical solution, the chemical damage and herbicidal effect on corn, wheat, soybeans, and various weeds were investigated according to the criteria of Test Example-1. The results are shown in Table 17. (Hereinafter, blank space) Test 1 - Test of weeding effect by soil treatment Vertical 15C1
1. Sterilized diluvial soil was placed in a plastic box with a width of 22 Cl and a depth of 6 Cl. 76°3555000 Test plate 21 A 5% emulsion of the compound of the present invention (a 25% hydrating powder is used depending on the compound) described in the insecticidal test specification against leafhopper was diluted with water containing a spreading agent. A chemical solution of 1000pp++'l11 degrees was prepared. A sufficient amount of this chemical solution was sprayed on the stems and leaves of rice planted in a 1/20,000 are pot. After air-drying, the cylinders were erected and 10 second instar larvae of the leafhopper, which is resistant to organophosphorus insecticides and carbamate insecticides, were released per pot.The cylinders were covered and stored in a thermostatic chamber. The investigation was conducted after 6 days had elapsed, and the mortality rate was calculated using the following formula. As a result, the following compounds showed a 100% mortality rate. Compound of the Invention A 5% emulsion of the compound of the present invention (25% hydrating powder was tested depending on the compound) described in the specification of the insecticidal test against the Japanese ladybug was diluted with water containing a spreading agent. Then, the chemical solution was adjusted to a concentration of 11,000 pp+, and tomato leaves were immersed in this chemical solution for about 10 seconds, air-dried, and then placed in a petri dish. The mice were then placed in a constant temperature room at 25°C, and the mortality rate after 6 days was calculated using the following formula. The test was conducted in two sections. As a result, the following compounds showed a 100% mortality rate. Compound of the present invention 11kL3 Trial 1 Continuous 2 J-Acaricidal efficacy test against two-spotted spider mites Green bean leaves were cut into circles with a diameter of 3.0 CIO using a leaf punch and placed on moist filter paper on a styrene cup with a diameter of 7 CI. . If you encounter one spider mite larva in this, one
0 animals were vaccinated. 5% of the compound of the invention described in the specification
Dilute the emulsion (25% permanant for some compounds) with water containing a spreading agent to make a chemical solution with a concentration of 11,000 pp. Spray this chemical solution at 2 ml per styrene cup using a rotary spreading base. and stored in a constant temperature room at 25℃.
The mortality rate after 96 hours was calculated using the following formula. The test was conducted in two sections. A 5% emulsion of the compound of the present invention described in the specification (25% permanant is used as a sample depending on the compound) is diluted with water containing a spreading agent to prepare a 1000pp+N1 degree chemical solution, and in this chemical solution, Kanlan is added. Leaves were soaked for about 10 seconds, air-dried, and placed in a petri dish, in which 10 2nd instar larvae of the diamondback moth were added per petri dish.
The heads were released and placed in a 25'C constant temperature room with a lid with a hole in them, and the mortality rate after 6 days was calculated using the following formula. The test was conducted in two sections. As a result, the following compounds showed a 100% mortality rate. Compound of the Invention 3 As a result, the following compounds showed a 100% mortality rate. Compound of the present invention N[L3

Claims (4)

[Claims] (1) Formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, X represents an oxygen atom or a sulfur atom, Y is a hydrogen atom, a halogen atom, a C_1 to C_4 alkyl group, C_1
~C_4 haloalkyl group, C_1-C_4 hydroxyalkyl group, C_2-C_4 alkoxyalkyl group, C_
2 to C_4 represents an alkylthioalkyl group, a cyano group, a thiocyanate group, or a nitro group, and R_f is C_1 to C
_6 represents a haloalkyl group, R is a hydrogen atom, an alkali metal, an alkaline earth metal, a C_1 to C_4 alkyl group, C
_2-C_4 alkenyl group, C_2-C_4 alkynyl group, C_1-C_4 haloalkyl group, C_2-C_4 alkoxyalkyl group, formyl group, C2-C_6 alkylcarbonyl group, C_2-C_6 alkoxycarbonyl group, C_2-C_6 alkoxycarbonylalkyl group,
C_2 to C_6 represents a cyanoalkyl group, benzyl group or phenyl group, and Het represents a 5-membered heterocycle, 6-membered heterocycle or fused heterocycle containing at least one nitrogen atom, oxygen atom or sulfur atom. ] Uracil derivative represented by. (2) A uracil derivative in which Het is represented by the following formula in formula (I) of claim (1). ▲There are mathematical formulas, chemical formulas, tables, etc.▼, ▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼,▲Mathematical formulas, chemical formulas,
There are tables, etc. ▼, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼
, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ [R1 is hydrogen atom, halogen atom, C_1 to C_8 alkyl group, C_3 to C_6 cycloalkyl group, C_1 to C
_8 haloalkyl group, C_3 to C_8 alkenyl group, C
_3-C_8 alkynyl group, C_3-C_6 cycloalkyl (C_1-C_4) alkyl group, C_1-C_6 alkoxy (C_1-C_4) alkyl group, C_1-C_
6 haloalkyloxy (C_1 to C_4) alkyl group,
C_1 to C_6 haloalkylthio group, C_1 to C_6 haloalkylsulfinyl group, C_1 to C_6 haloalkylsulfonyl group, cyano group, substituted phenyl group (as substituents, hydrogen atom, halogen atom, C_1 to C_4 alkyl group, C_1 to C_4 alkoxy group, C_1-C_4 alkoxycarbonyl group, C_1-C_4 haloalkyl group, C_1-C_4 haloalkoxy group, C_1-C_4 alkylthio group, C_1-C_4 haloalkylthio group, C
_1-C_4 alkylsulfonyl group, C_1-C_4 halokylsulfonyl group, C_1-C_4 alkoxycarbonyl group, carboxyl group, amino group, C_1-C_4
Represents an alkylamino group, a C_1-C_4 dialkylamino group, a cyano group, a phenyl group, a benzyl group, a methylenedioxy group, a haromethylenedioxy group, and a nitro group. ),
Substituted benzyl group (the substituent has the same meaning as substituted phenyl group), substituted phenoxy (C_1 to C_4)
Alkyl group (represents the same meaning as a substituted phenyl group as a substituent), substituted phenylthio (C_1-C_4) alkyl group (represents the same meaning as a substituted phenyl group as a substituent), substituted benzylthio (C_1- C_4) Alkyl group (as a substituent, the same meaning as a substituted phenyl group is expressed), substituted benzylthio (C_1 to C_4) alkyl group (as a substituent, the same meaning as a substituted phenyl group is expressed), C_1 to C_6 Alkylthio group, C_1-C_
6 alkylsulfonyl group, C_1-C_6 alkylsulfinyl group, CO_2R7 (R7 is a hydrogen atom, C_1-
C_8 represents an alkyl group, phenyl group, or benzyl group. )
, CON(R8)R9 (R8 and R9 are each independently a hydrogen atom, a C_1 to C_8 alkyl group, a C_1 to C_
2-alkylsulfonyl group, phenyl group, benzyl group, C
It represents a _3-C_6 alkenyl group or a C_3-C_6 alkynyl group, and R8 and R9 may form a 3- to 6-membered ring composed of any atoms among carbon atoms, oxygen atoms, and sulfur atoms. ), SO_2N(R8)R9 (R8, R9 represent the same meanings as above), N(R8)R9 (R8, R9 represent the same meanings as above), or OR11 (R11 is a hydrogen atom, C_1 ~C_8 alkyl group, C_3~C_8 alkenyl group, C_3~C_8 alkynyl group, C_1~C_
8 haloalkyl group, phenyl group, benzyl group, CH_2
CO_2R12 (R12 represents a hydrogen atom, C_1 to C_8 alkyl group) or CH_2CON(R8)R9
(R8 and R9 represent the same meanings as above). R2 is a hydrogen atom, a halogen atom, a C_1 to C_6 alkyl group, a C_1 to C_6 haloalkyl group, or a C_1 to
C_6 represents an alkoxy group. R3 represents a hydrogen atom, a halogen atom, a C_1-C_6 alkyl group, a C_1-C_6 haloalkyl group, or a C_1-C_6 haloalkoxy group. R4 and R5 are each independently a hydrogen atom, a halogen atom, a C_1-C_8 alkyl group, a C_3-C_8 alkenyl group, a C_3-C_8 alkynyl group, a C_1-C
_8 represents a haloalkyl group, a C_1 to C_6 alkoxy group, or N(R8)R9 (R8 and R9 have the same meanings as above). R6 is a C_1 to C_6 alkyl group, C_
Represents a 3-C_6 alkenyl group, a C_3-C_6 alkynyl group, or a C_1-C_6 haloalkyl group. n represents an integer from 1 to 3. ] Uracil derivative represented by. (3) A herbicide containing one or more of the uracil derivatives according to claim (1) as an active ingredient. (4) A pest control agent containing one or more of the uracil derivatives according to claim (1) as an active ingredient.