CN101130521A - Novel pyrimidine derivative with obvious biological activity - Google Patents

Novel pyrimidine derivative with obvious biological activity Download PDF

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Publication number
CN101130521A
CN101130521A CNA2007101512736A CN200710151273A CN101130521A CN 101130521 A CN101130521 A CN 101130521A CN A2007101512736 A CNA2007101512736 A CN A2007101512736A CN 200710151273 A CN200710151273 A CN 200710151273A CN 101130521 A CN101130521 A CN 101130521A
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China
Prior art keywords
chch
nematode
cch
compound
mite
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Chinese (zh)
Inventor
宁君
陈作红
张涛
梅向东
张建军
赵前飞
李永红
马洪菊
杨国权
宋倩
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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Institute of Plant Protection of Chinese Academy of Agricultural Sciences
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Priority to CNA2007101512736A priority Critical patent/CN101130521A/en
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Abstract

The invention discloses a new typed fluorine pyrimidine derivative and making method with parasiticide, acaricide, nematocide, sterilization and weeding activity, which also provides the composition of the derivative and killing or controlling method of insect, mite, nematology, disinfection and weeding through the derivative.

Description

Novel poyrimidine derivatives with obvious biological activity
Technical field
The present invention relates to have desinsection, kill the pyrimidine derivatives and preparation method thereof of the novel fluorine of mite, nematicide and sterilization and weeding activity, contain the composition of this derivative, kill or control insect, mite class, nematode, reach the method for sterilization and weeding with this derivative.
Background technology
Patent US0173190, WO9524403, GB9219634, GB9316219, US5952359, GB9705120, US6448262, US7105524 etc. disclose and have contained 4 in recent years, 4-two fluoro-3-butenyl heterocyclic derivatives, US106027, WO005282, patents such as EP1091957, CN97117398 also disclose many pyrimidine derivatives that contain pyrazoles simultaneously.These compounds have nematicide, desinsection, acaricidal activity, and some compound also has sterilization and weeding activity.Yet, not the appearing in the newspapers of the fluorine-containing pyrimidine derivatives among the present invention.
Summary of the invention
In order to satisfy the requirement on the agricultural, the invention provides the preparation of pyrimidine derivatives of novel fluorine and on agricultural, prevent and treat the application of parasitosis crop smothering and contain the using method of these compound compositions.Fluorine-containing pyrimidine derivatives provided by the invention is controlling plant insect, mite class, nematode, germ and weeds effectively.
The present invention proposes and relate to following general formula (I) and pyrimidine derivatives (II)
Figure A20071015127300051
Wherein, R 1Can be following structure
Figure A20071015127300052
R 2Can be halogen atoms such as hydrogen atom, fluorine, chlorine, low alkyl group, lower alkoxy, perhaps group such as aralkyl, aralkoxy;
X is O, S, NH etc.;
A is a hydrogen atom, halogen atoms such as fluorine, chlorine, and low alkyl group, lower alkoxy, trifluoromethyls etc. contain methyl fluoride, perhaps group such as aralkyl, aralkoxy
Compound among the present invention can be synthetic by several different methods, and for example figure below is depicted as wherein feasible synthetic route.
Wherein, reactant (III), (IV), (V) all are commercially available, also can be synthetic by the currently known methods laboratory.Concrete synthetic method is seen examples of implementation.
With specific examples the present invention is described further below, but does not limit the present invention.Part of compounds sees Table 1 and table 2.
Table 1
Figure A20071015127300062
X＝O，N，S
R 1=F 2C=CHCH 2Perhaps F 2C=CHCH 2CH 2
R 2＝H，CH 3，Cl，F，CH 3O
Numbering R 1 X R 2
1 F 2C＝CHCH 2 O H
2 F 2C＝CHCH 2 S H
3 F 2C＝CHCH 2 N H
4 F 2C＝CHCH 2CH 2 O H
5 F 2C＝CHCH 2CH 2 S H
6 F 2C＝CHCH 2CH 2 N H
7 F 2C＝CHCH 2CH 2 O CH 3
8 F 2C＝CHCH 2CH 2 O Cl
9 F 2C＝CHCH 2CH 2 O F
10 F 2C＝CHCH 2CH 2 O CH 3O
Table 2
Figure A20071015127300071
X＝O，N，S
R 1＝F 2C＝CHCH 2，F 2C＝CHCH 2CH 2，HC≡CCH 2O，
HC≡CCH 2CH 2O，Cl 2C＝CHCH 2O，H 2C＝CHCH 2O
R 2＝H，CH 3，Cl，F，CH 3O
A＝H，CH 3，Cl，F，CH 3O，CF 3
Numbering R 1 R 2 X A
11 F 2C＝CHCH 2 H O H
12 F 2C＝CHCH 2CH 2 H O H
13 HC≡CCH 2 H O H
14 HC≡CCH 2CH 2 H O H
15 Cl 2C＝CHCH 2 H O H
16 H 2C＝CHCH 2 H O H
17 F 2C＝CHCH 2 H N H
18 F 2C＝CHCH 2 H N H
19 F 2C＝CHCH 2CH 2 H S H
20 F 2C＝CHCH 2CH 2 H S H
21 F 2C＝CHCH 2 H O CH 3
22 F 2C＝CHCH 2CH 2 H O CH 3
23 HC≡CCH 2 H O CH 3
24 HC≡CCH 2CH 2 H O CH 3
25 Cl 2C＝CHCH 2 H O CH 3
26 H 2C＝CHCH 2 H O CH 3
27 F 2C＝CHCH 2 H N CH 3
28 F 2C＝CHCH 2 H N CH 3
29 F 2C＝CHCH 2CH 2 H S CH 3
30 F 2C＝CHCH 2CH 2 H S CH 3
31 F 2C＝CHCH 2 H O Cl
32 F 2C＝CHCH 2CH 2 H O Cl
33 HC≡CCH 2 H O Cl
34 HC≡CCH 2CH 2 H O Cl
35 Cl 2C＝CHCH 2 H O Cl
36 H 2C＝CHCH 2 H O Cl
37 F 2C＝CHCH 2 H N Cl
38 F 2C＝CHCH 2 H N Cl
39 F 2C＝CHCH 2CH 2 H S Cl
40 F 2C＝CHCH 2CH 2 H S Cl
41 F 2C＝CHCH 2 H O F
42 F 2C＝CHCH 2CH 2 H O F
43 HC≡CCH 2 H O F
4 HC≡CCH 2CH 2 H O F
45 Cl 2C＝CHCH 2 H O F
46 H 2C＝CHCH 2 H O F
47 F 2C＝CHCH 2 H N F
48 F 2C＝CHCH 2 H N F
49 F 2C＝CHCH 2CH 2 H S F
50 F 2C＝CHCH 2CH 2 H S F
51 F 2C＝CHCH 2 H O CH 3O
52 F 2C＝CHCH 2CH 2 H O CH 3O
53 HC≡CCH 2 H O CH 3O
54 HC≡CCH 2CH 2 H O CH 3O
55 Cl 2C＝CHCH 2 H O CH 3O
56 H 2C＝CHCH 2 H O CH 3O
57 F 2C＝CHCH 2 H N CH 3O
58 F 2C＝CHCH 2 H N CH 3O
59 F 2C＝CHCH 2CH 2 H S CH 3O
60 F 2C＝CHCH 2CH 2 H S CH 3O
61 F 2C＝CHCH 2 H O CF 3
62 F 2C＝CHCH 2CH 2 H O CF 3
63 HC≡CCH 2 H O CF 3
64 HC≡CCH 2CH 2 H O CF 3
65 Cl 2C＝CHCH 2 H O CF 3
66 H 2C＝CHCH 2 H O CF 3
67 F 2C＝CHCH 2 H N CF 3
68 F 2C＝CHCH 2 H N CF 3
69 F 2C＝CHCH 2CH 2 H S CF 3
70 F 2C＝CHCH 2CH 2 H S CF 3
71 F 2C＝CHCH 2CH 2 CH 3 O H
72 F 2C＝CHCH 2CH 2 CH 3 O CH 3
73 F 2C＝CHCH 2CH 2 CH 3 O Cl
74 F 2C＝CHCH 2CH 2 CH 3 O F
75 F 2C＝CHCH 2CH 2 CH 3 O CH 3O
76 F 2C＝CHCH 2CH 2 CH 3 O CF 3
77 F 2C＝CHCH 2CH 2 CH 3 N H
78 F 2C＝CHCH 2CH 2 CH 3 N CH 3
79 F 2C＝CHCH 2CH 2 CH 3 N Cl
80 F 2C＝CHCH 2CH 2 CH 3 N F
81 F 2C＝CHCH 2CH 2 CH 3 N CH 3O
82 F 2C＝CHCH 2CH 2 CH 3 N CF 3
83 F 2C＝CHCH 2CH 2 CH 3 S H
84 F 2C＝CHCH 2CH 2 CH 3 S CH 3
85 F 2C＝CHCH 2CH 2 CH 3 S Cl
86 F 2C＝CHCH 2CH 2 CH 3 S F
87 F 2C＝CHCH 2CH 2 CH 3 S CH 3O
88 F 2C＝CHCH 2CH 2 CH 3 S CF 3
89 F 2C＝CHCH 2CH 2 Cl O H
90 F 2C＝CHCH 2CH 2 Cl O CH 3
91 F 2C＝CHCH 2CH 2 Cl O Cl
92 F 2C＝CHCH 2CH 2 Cl O F
93 F 2C＝CHCH 2CH 2 Cl O CH 3O
94 F 2C＝CHCH 2CH 2 Cl O CF 3
95 F 2C＝CHCH 2CH 2 Cl N H
96 F 2C＝CHCH 2CH 2 Cl N CH 3
97 F 2C＝CHCH 2CH 2 Cl N Cl
98 F 2C＝CHCH 2CH 2 Cl N F
99 F 2C＝CHCH 2CH 2 Cl N CH 3O
100 F 2C＝CHCH 2CH 2 Cl N CF 3
101 F 2C＝CHCH 2CH 2 Cl S H
102 F 2C＝CHCH 2CH 2 Cl S CH 3
103 F 2C＝CHCH 2CH 2 Cl S Cl
104 F 2C＝CHCH 2CH 2 Cl S F
105 F 2C＝CHCH 2CH 2 Cl S CH 3O
106 F 2C＝CHCH 2CH 2 Cl S CF 3
107 F 2C＝CHCH 2CH 2 F O H
108 F 2C＝CHCH 2CH 2 F O CH 3
109 F 2C＝CHCH 2CH 2 F O Cl
110 F 2C＝CHCH 2CH 2 F O F
111 F 2C＝CHCH 2CH 2 F O CH 3O
112 F 2C＝CHCH 2CH 2 F O CF 3
113 F 2C＝CHCH 2CH 2 F N H
114 F 2C＝CHCH 2CH 2 F N CH 3
115 F 2C＝CHCH 2CH 2 F N Cl
116 F 2C＝CHCH 2CH 2 F N F
117 F 2C＝CHCH 2CH 2 F N CH 3O
118 F 2C＝CHCH 2CH 2 F N CF 3
119 F 2C＝CHCH 2CH 2 F S H
120 F 2C＝CHCH 2CH 2 F S CH 3
121 F 2C＝CHCH 2CH 2 F S Cl
122 F 2C＝CHCH 2CH 2 F S F
123 F 2C＝CHCH 2CH 2 F S CH 3O
124 F 2C＝CHCH 2CH 2 F S CF 3
125 F 2C＝CHCH 2CH 2 CH 3O O H
126 F 2C＝CHCH 2CH 2 CH 3O O CH 3
127 F 2C＝CHCH 2CH 2 CH 3O O Cl
128 F 2C＝CHCH 2CH 2 CH 3O O F
129 F 2C＝CHCH 2CH 2 CH 3O O CH 3O
130 F 2C＝CHCH 2CH 2 CH 3O O CF 3
131 F 2C＝CHCH 2CH 2 CH 3O N H
132 F 2C＝CHCH 2CH 2 CH 3O N CH 3
133 F 2C＝CHCH 2CH 2 CH 3O N Cl
134 F 2C＝CHCH 2CH 2 CH 3O N F
135 F 2C＝CHCH 2CH 2 CH 3O N CH 3O
136 F 2C＝CHCH 2CH 2 CH 3O N CF 3
137 F 2C＝CHCH 2CH 2 CH 3O S H
138 F 2C＝CHCH 2CH 2 CH 3O S CH 3
139 F 2C＝CHCH 2CH 2 CH 3O S Cl
140 F 2C＝CHCH 2CH 2 CH 3O S F
141 F 2C＝CHCH 2CH 2 CH 3O S CH 3O
142 F 2C＝CHCH 2CH 2 CH 3O S CF 3
The invention described above compound can be controlled harmful insect such as lepidopteran, Diptera, Homoptera and Coleoptera and some other no vertebra insect of various agricultural, gardening, forest and storage, as the mite class.For example, seven kinds of above-mentioned compounds can be controlled following insect and mite class:
Myzus persicae (black peach aphid), Aphis gossypii (cotten aphid), Aphis fabae (vegetable aphid), Aedes aegypti (mosquito), Anopheles spp. (Anopheles), Culex spp. (Culex), Dysdercus fasciatus (band line red cotton bug), Muscadomestica (housefly), Pieris brassicae (large white butterfly), Plutella xlostella (small cabbage moth), Phaedon cochleariae (the horseradish ape is chrysomelid), Aonidiella spp. (kidney Aspidiotus genus), Trialeurodes spp. (Aleyrodes), Bemisia tabaci (sweet genus aleyrodid), Blattella germanica (Groton bug), Periplaneta americana (periplaneta americana), Blatta orientalis (East Africa Lian), Spodoptera littoralis (prodenia litura), Heliothis virescens (oriental tobacco budworm), Chortiocetes terminifera (Australian locust), Diabrotica spp. (the chrysomelid genus of bar), Agrotis spp. (Agrotis), Chilo partellus (Pyrausta nubilalis (Hubern).), Nilaparvata lugens (brown paddy plant hopper), Nephotettix cincticeps (rice green leafhopper), Panonychus ulmi (panonychus ulmi), Panonychus citri (tangerine Panonychus citri), Tetranychus urticae (Tetranychus urticae), Tetranychus cinnabarinus (carmine spider mite), Phyllcoptruta oleivora (citrus rust mite), Polyphagotarsonemus latus (white spider) and Brevipalpus spp. (short hairs mite).
The compounds of this invention also can be used for preventing and treating nematode, mainly prevents and treats plant nematode such as root knot nematode: Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne kind; Roe deer capsule nematode: Globoderarostochiensis and other Globodera kind; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii and other Heterodera kind; Plant the knurl nematode: Anguina species; Stem and leaf bud nematode: Aphelenchoides species; Thorn nematode: Belonolaimus longicaudatus and other Belonolaimus kind; Pine wood nematode: Bursaphelenchus xylophilus and other Bursaphelenchus kind; Annular nematode: Criconema kind, Criconemella kind, Criconemoides kind, Mesocriconema kind; Bulb eelworm: Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus kind; Awl nematode: Dolichodorus kind; Helicotylenchus: Heliocotylenchusmulticinctus and other Helicotylenchus kind; Sheath nematode: Hemicycliophora kind and Hemicriconemoides kind; The Hirshmanniella kind; Hat nematode: Hoploaimus kind; Pseudo-root nodule nematode: Nacobbus kind; Needlework worm: Longidoruselongatus and other Longidorus kind; Nail nematode: Paratylenchus kind; Pratylenchus: Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus kind; Similes thorne: Radopholus similis and other Radopholus kind; Kidney shape nematode: Rotylenchus robustus and other Rotylenchus kind, Scutellonema kind; Undesirable root nematode: Trichodorus primitivus and other Trichodorus kind, Paratrichodorus kind; Downgrade nematode: Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus kind; Citrus nematode: Tylenchulus kind; Sword nematode: Xiphinema kind and other plant nematode.
The compounds of this invention also can be used as sterilant, prevents and treats the various plants pathogenic bacteria.
The compounds of this invention is useful as herbicides also, the plant of preventing and kill off multiple weeds and not expecting, and prevent and kill off the plant that other weedicide is produced resistance.
The compounds of this invention is particularly useful for control to the deleterious insect of plant, mite class and nematode.
In order to use above-mentioned target compound control harmful insect, mite class, nematode etc., need be made into corresponding compositions, contain the described compound of claim 1 of 0.1-99% weight in the said composition.Compound can be made composition such as pulvis, wettable powder, granula (slowly-releasing or quick-release), missible oil, suspension agent, aqua, emulsifiable concentrate, microemulsion, coating agent for seed, smoke substance, may command release dosage form such as the microcapsule granula or the suspension agent etc. of various ways, be applied to soil, plant or seed, and mix in bait, or be put into the place that insect haunts.When in soil that is applied to plant or plantation or the water, be scattered in the water during use or in other liquid medium, effectively working concentration is usually at 0.1ppm to 10000ppm, preferred 1ppm to 5000ppm.
These compounds can the single-component form use, and also can use with as sterilant, synergistic agent, weedicide, sterilant or plant-growth regulator with suitable one or more biological activities.Other effective ingredient that is suitable for comprises the compound that can enlarge activity profile or prolong the lasting period, can strengthen the compound of the active of target compound or enhancing quick-acting.Other effective ingredient in the mixture, especially wanting can increase the result of use of target compound and will have the different mechanism of action.Target compound can be with desinsections such as pyrethroid, organic phosphates, amino formate, chlorinated cyclopentadiene class, formamidine, organic tin, chlorinated hydrocarbons, benzoyl area kind, pyroles, kill mite and nematocides is used with.
Embodiment
Following specific embodiment is used for further specifying the present invention.
Synthetic embodiment
Synthesizing of example 1 compound (4)
Figure A20071015127300161
Under the room temperature, add 5.96g (40mmol) 4 in the 100ml tetrahydrofuran (THF), the 6-dichloro pyrimidine adds the 0.48g sodium hydride in batches after the dissolving, stir white opacity suspension; Dropwise add 30ml then and contain 4, the THF solution of 4-two fluoro-3-alkene-butanols 1.08g (10mmol) continues to stir 30min, is warming up to backflow gradually, continues reaction 5 hours.After reaction was finished, THF was put in order out in decompression, and gained solid water and acetic acid ethyl fluid liquid distribute, and organic phase concentrates, and column chromatography for separation gets white solid 1.8g, yield 81.8%.
This white solid is dissolved among the 100ml THF, adds the 0.24g sodium hydride, stir the back and add the 1.83g m fluorophenol, the post-heating that stirs was to back flow reaction 12 hours.
Product pressure reducing and steaming THF adds water and ethyl acetate separatory, and organic phase concentrates the back column chromatography, gets the 1.6g white crystal, yield 66.95%.Nuclear magnetic data: 1HNMR, 300MHZ, interior mark TSM, solvent C DCl 3, d:2.38 (2H, m), 3.98 (2H, t), 4.28 (1H, t), 6.20 (1H, s), 6.50 (3H, m), 7.07 (1H, m), 8.09 (1H, s)
Synthesizing of example 2 compounds (24)
Figure A20071015127300171
Under the room temperature, add 5.96g (40mmol) 4 in the 100ml tetrahydrofuran (THF), the 6-dichloro pyrimidine adds the 0.48g sodium hydride in batches after the dissolving, stir white opacity suspension; Dropwise add 50ml then and contain the THF solution of 3-alkynes-1-butanols 1.4g (20mmol), continue to stir 30min, be warming up to backflow gradually, continue reaction 4 hours.After reaction was finished, THF was put in order out in decompression, and products therefrom water and acetic acid ethyl fluid liquid distribute, and organic phase concentrates, and column chromatography for separation gets white solid 2.3g, yield 63.18%.
This white solid is dissolved among the 100ml THF, adds the 0.4g sodium hydride, stir the back and add 1.9g 3-methyl-5 trifluoromethyls-pyrazoles, the post-heating that stirs was to back flow reaction 12 hours.
Product pressure reducing and steaming THF adds water and ethyl acetate separatory, and organic phase concentrates the back column chromatography, gets the 2.85g white crystal, yield 76.4%.Nuclear magnetic data: 1HNMR, 300MHZ, interior mark TSM, solvent C DCl 3, d:1.82 (1H, t), 2.45 (2H, t), 2.79 (3H, s), 4.11 (2H, t), 5.90 (1H, s), 6.90 (1H, s), 9.00 (1H, s).
Example of formulations (add-on of active ingredient is metered into after rolling over hundred in the prescription, and all percentage compositions are weight percentage)
Example 3 10% compound (5) missible oil
Compound (5) 10%, farming breast No. 500 5%, farming breast No. 601 5%, methyl alcohol 10%, dimethylbenzene complements to 100%.Above-mentioned material mixes, and promptly obtains transparence missible oil.
Example 4 10% compound (74) wettable powders
Compound (74) 10%, Sodium dodecylbenzene sulfonate 1.5%, carboxymethyl cellulose 1%, sulfonaphthol formaldehyde condensation products sodium salt 8%, light calcium carbonate complements to 100%.Above-mentioned material thorough mixing after ultrafine crusher is pulverized, promptly obtains converted products,
Example 5 60% compound (14) water dispersible granules
Compound (14) 60%, methyl naphthalene sulfonate formaldehyde condensate 12%, epoxidized polyether 5%, Zulkovsky starch 15%, gypsum complements to 100%.Above-mentioned material mixing after the kneading, adds in the tablets press that the certain specification screen cloth is housed and carries out granulation, and drying, screening obtain granule then.
Biological activity determination
Example 6 pesticide and miticide actilities are measured
With The compounds of this invention several insects and mite class have been carried out the insecticidal activity assay test.Method for measuring is as follows:
After the mixed solvent dissolving of new compound with acetone/methanol (1: 1), be diluted to required concentration with the water that contains 0.1% tween 80.
With Myzus persicae (black peach aphid), Culex pippenspallens (culex pipiens pollens), Musca domestica (housefly), Plutella xlostella (small cabbage moth), Heliothis virescens (oriental tobacco budworm), Nilaparvata lugens (brown paddy plant hopper), Tetranychus cinnabarinus (carmine spider mite) is target, adopt airbrush spray method and immersion method (culex pipiens pallens larvae) to carry out insecticidal activity assay, airbrush spraying processing pressure is that 10psi (is roughly equal to 0.7kg/cm 2), spouting liquid is 0.5ml.Handle the mortality ratio that 2-3 day is investigated target in the back.
The partial test result is as follows:
When liquor strength was 50ppm, compound (6) was equal 100% to the mortality ratio of black peach aphid, carmine spider mite, housefly,, other target insect mortality ratio also surpasses 95%.

Claims (5)

1. pyrimidine derivatives structural formula involved in the present invention is as follows:
Figure A2007101512730002C1
R1＝F 2C＝CHCH 2，F 2C＝CHCH 2CH 2，HC≡CCH 2O，HC≡CCH 2CH 2O，Cl 2C＝CHCH 2O H 2C＝CHCH 2O
R2＝H，CH3，Cl，F，CH3O
A＝H，CH3，Cl，F，CH3O，CF3
The described compound of claim 1 the preparation method, by following trans should making:
Figure A2007101512730002C2
3. the described compound of claim 1 is being prevented and treated plant insect, mite class, nematode, and the application of germ and weeds.
4. the described compound of claim 1 is particularly useful for pest control, mite class, nematode.
A desinsection, kill mite, nematicidal composition, it is characterized in that: contain the described fluorine-containing pyrimidine derivatives of claim 1 in the composition, the weight percentage of active ingredient is 0.1-99%.
CNA2007101512736A 2007-09-18 2007-09-18 Novel pyrimidine derivative with obvious biological activity Pending CN101130521A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010119879A1 (en) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Pyrimidine compound and its use for pest control
WO2010119878A1 (en) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Pyrimidine compound and its use for pest control

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010119879A1 (en) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Pyrimidine compound and its use for pest control
WO2010119878A1 (en) * 2009-04-16 2010-10-21 Sumitomo Chemical Company, Limited Pyrimidine compound and its use for pest control

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