CN114644596B - Fluoropyrimidine aromatic amine compound and application thereof - Google Patents
Fluoropyrimidine aromatic amine compound and application thereof Download PDFInfo
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- -1 Fluoropyrimidine aromatic amine compound Chemical class 0.000 title claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 11
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 239000000575 pesticide Substances 0.000 claims description 16
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001276 controlling effect Effects 0.000 claims 1
- 241000500437 Plutella xylostella Species 0.000 abstract description 11
- 230000002147 killing effect Effects 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000003814 drug Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WPALTCMYPARVNV-UHFFFAOYSA-N tolfenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)=C1Cl WPALTCMYPARVNV-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241000813090 Rhizoctonia solani Species 0.000 description 3
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OIXRLPWNVSSGHR-UHFFFAOYSA-N 2-butylsulfanyl-6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound CCCCSC1=NC(=O)C=C(C(F)(F)F)N1 OIXRLPWNVSSGHR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 240000007124 Brassica oleracea Species 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- 241001477931 Mythimna unipuncta Species 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YZAOETRYQWFEOY-UHFFFAOYSA-N 2-sulfanylidene-6-(trifluoromethyl)-1h-pyrimidin-4-one Chemical compound FC(F)(F)C1=CC(=O)NC(=S)N1 YZAOETRYQWFEOY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- JRFZJTURWQMISD-UHFFFAOYSA-N CC1=C(C(C=C2)=C(C(F)(F)F)C=C2OC2=CC=CC=C2)C(NC(C=CC(F)=C2)=C2Cl)=NC(C)=N1 Chemical compound CC1=C(C(C=C2)=C(C(F)(F)F)C=C2OC2=CC=CC=C2)C(NC(C=CC(F)=C2)=C2Cl)=NC(C)=N1 JRFZJTURWQMISD-UHFFFAOYSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000409991 Mythimna separata Species 0.000 description 1
- 241000231139 Pyricularia Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000000447 pesticide residue Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000012865 response to insecticide Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention provides a fluorine-containing pyrimidine arylamine compound and application thereof, and the structure is shown as a formula I:
Description
The invention belongs to the field of pesticides in pesticides, and relates to a fluoropyrimidine aromatic amine-containing pesticide and a method for controlling pests in agriculture or forestry by using the fluoropyrimidine aromatic amine-containing pesticide.
Background art agricultural pests harm the growth of crops, resulting in reduced yields and reduced quality. At present, pest control mainly depends on chemical pesticides, and due to the fact that a large number of pesticides are frequently used, the pests generate serious drug resistance to the pesticides, so that a series of problems of larger and larger drug consumption, lower prevention effect, shortened duration, high pesticide residue and the like are caused. The development and application of novel pesticides with different action mechanisms are effective means for solving the problem of pest resistance. The literature [ Wu Ningjie, long Cheng, etc. ] the synthesis of novel 4-arylaminopyrimidine derivatives and their insecticidal activity [ J ]. Organic chemistry, 2019 (39): 852-856 ] reports a class of 4-arylaminopyrimidine derivatives, and biological activity tests show that the mortality rate of the series of compounds to armyworms (Mythimna separata) is 100% when the mass concentration is 500 mg/L; and when the mass concentration is reduced to 20mg/L, the mortality rate of the compound 2-methyl-4- [ N- (2-chloro-4-fluorophenyl) amino ] -5- [ 2-trifluoromethyl-4- (phenoxy) phenyl ] -6-methylpyrimidine to armyworm and plutella xylostella is 80% and 60%, respectively.
In the prior art, the fluorine-containing pyrimidine arylamine compound (formula I) is not disclosed.
The invention aims to provide a pesticide which has novel structure, simple and convenient synthesis method, safety and high efficiency and can be used for preventing and controlling agricultural or forestry pests.
The technical scheme of the invention is as follows:
a fluorine-containing pyrimidine arylamine compound and application thereof are shown in the formula I:
the compounds of formula I of the present invention can be prepared by the following reaction scheme:
the compound of the formula II and the compound of the formula III are subjected to substitution reaction in acetonitrile by using triethylamine as a catalyst at room temperature to prepare the compound of the formula I. The specific preparation method is shown in the embodiment of the invention.
The invention has the advantages and positive effects that:
the compound of the invention is used as agricultural pesticide, and has the advantages of novel structure, simple preparation and certain bactericidal effect. The compound has an excellent effect of inhibiting and killing plutella xylostella, and can achieve an excellent effect on agricultural and forestry pests. Compared with commercialized pesticide tolfenpyrad, the compound I has slightly higher killing activity on plutella xylostella than tolfenpyrad, and the killing rate on plutella xylostella reaches 97% at extremely low concentration of 10 mg/L. The compound is a fluorine-containing nitrogen heterocyclic compound, has the characteristics of high biological activity, low toxicity to beneficial organisms, easy degradation and good environmental compatibility, is particularly suitable for the treatment of the existing drug-resistant agricultural pests, and has good development and application prospects as a novel pesticide variety with excellent insecticidal and bactericidal effects.
The compound of the invention can be used singly or in combination with other active substances to improve the comprehensive performance of the product.
The invention also includes pesticide compositions containing the compounds of formula I as active ingredients, wherein the weight percentage of the active ingredients in the composition is 1-99%. The pesticide composition also includes an agriculturally or forestry acceptable carrier.
It should be understood that various changes and modifications can be made within the scope of the present invention as defined in the appended claims.
Detailed Description
The following synthetic examples, green test results, are useful for further illustration of the invention and are not meant to limit the invention.
Synthesis example
Example 1 preparation of Compound I:
(1) Synthesis of intermediate compounds of formula ii:
in a 250mL three-port reaction flask, 19.62g (0.10 mol) of 2-mercapto-4-hydroxy-6-trifluoromethyl pyrimidine and 16.59g (0.12 mol) of potassium carbonate are added into 50mL of DMF, and after stirring at room temperature for 10min, 15.07g (0.11 mol) of n-bromobutane is added dropwise, after the dropwise addition, the reaction is completed at room temperature for 3h, TLC monitors that the reaction is complete, the reaction solution is poured into 150mL of water, hydrochloric acid is added dropwise to be neutral under stirring, and a solid is separated. Suction filtering, washing, collecting filter cake and drying to obtain the compound 2-n-butylsulfanyl-4-hydroxy-6-trifluoromethyl pyrimidine, wherein the yield is 87%.
In a 250mL three-necked flask, 25.5g (0.1 mol) of 2- (n-butylsulfanyl) -4-hydroxy-6-trifluoromethyl pyrimidine was added to 100mL of thionyl chloride, stirred, added with a catalytic amount of DMF, heated to reflux, reacted for 3 hours, detected by TLC to complete the reaction, and distilled under reduced pressure to remove the remaining thionyl chloride. The next reaction was carried out directly without purification.
(2) Synthesis of Compound I:
in a 100mL three-necked flask, 2.71g (10.0 mmol) of the compound of formula II and 1.21g (12.0 mmol) of triethylamine were added to 20mL of acetonitrile, stirred at room temperature for 0.5h, 3.43g (10.5 mmol) of 2, 5-dichloro-4- (1, 2, 3-hexafluoropropoxy) aniline was added in portions, the reaction was continued at room temperature for 3 to 5h, and completion of the reaction was detected by TLC. The reaction solution was added to 60mL of water, stirred, and a crude solid product was precipitated, and the crude solid product was separated by column chromatography (V (ethyl acetate): V (petroleum ether) =1:10) to give the target compound i in a yield of 71%. White solid, m.p.85.7-87 ℃.
The nuclear magnetic data of the compounds of formula I of the present invention are as follows:
1 H NMR(500MHz,DMSO-d 6 )δ9.98(s,1H),8.19(s,1H),7.70(s,1H),7.05(s,1H),6.51(d,J＝41.3Hz,1H),2.91(t,J＝7.5Hz,2H),1.52–1.44(m,2H),1.26–1.19(m,2H),0.76(t,J＝7.6Hz,3H).
13 C NMR(126MHz,DMSO)δ171.99,160.83,153.40,153.12,152.85,152.57,140.58,134.72,127.66,126.32,125.26,124.52,121.55,119.37,99.24,84.86,84.58,84.31,84.03,83.31,83.03,82.75,82.48,39.95,39.78,39.62,39.45,39.28,39.11,38.95,30.89,29.77,21.28,13.12。
biological Activity test
Example 2 method for measuring insecticidal Activity
And selecting plutella xylostella as a target for insecticidal activity test. The insecticidal activity of plutella xylostella was tested by the leaf dipping method (i.e. as proposed by the international committee on pesticide resistance action Insecticide Resistance Action Committee, IRAC). The specific operation method comprises the following steps: soaking cabbage leaves in the prepared medicinal liquid for 3-5s with straight ophthalmic forceps, taking out the tablet, removing redundant medicinal liquid, soaking 1 cabbage leaf each time, performing three parallel experiments on each sample, and placing the leaves on the treatment paper according to the marking sequence. After the liquid medicine on the leaf is dried, the leaf is respectively put into marked straight test tubes with the length of 10cm, 30 heads of 3-year-old plutella xylostella larvae are respectively inoculated in each test tube, and the mouth of the tube is covered by gauze and then is placed in a standard culture room. The test uses tolfenpyrad as a positive control medicament and clean water as a negative control medicament. After 48 hours, the experimental result is observed, and the death judgment standard of the plutella xylostella is as follows: the insect body is shrunken and blackened, and no obvious reaction is caused after the light touch test with the writing brush; the standard for judging the living insects is as follows: the insect body is moist, fresh and cleaned by a writing brush and kept dynamic. Mortality (%) was calculated from the investigation result.
Mortality (%) = [ (agent treatment mortality-placebo mortality)/(1-placebo mortality) ]. 100
Table 1 results of Plutella xylostella killing Activity test of Compounds of formula I
The test result shows that the compound I has slightly better killing effect on plutella xylostella than tolfenpyrad, and the killing rate reaches 97% under the ultra-low concentration of 10 mg/L.
Example 3 determination of Bactericidal Activity
The test method uses a fungus growth inhibition method, and the culture medium is potato grape agar medium (PDA) with the concentration of 50 mug/mL. The specific operation method comprises the following steps: under the aseptic environment, 0.5mL of the mother solution of the medicament to be detected is absorbed and added into a culture dish, 9.5mL of PDA culture medium is additionally added, the culture dish is uniformly shaken to form a 50mL medicament-containing flat plate, then a bacterial disc with the diameter of 4mm is intercepted by a puncher along the outer edge of hypha, the bacterial disc is transplanted onto the medicament-containing flat plate, the culture dish is placed into an incubator and cultured for 72 hours at the temperature of 24+/-1 ℃, the diameter of the bacterial disc is observed, the relative inhibition rate of the bacterial disc is calculated, the treatment is repeated for three times, and the average value is obtained. The strains tested were: sclerotinia sclerotiorum (Sclerotinia sclerotiorum (lib.) de Bary), gibberella wheat (Fusarium graminearum schw.), pyricularia oryzae (Pyricularia oryae Cav), rhizoctonia solani (Rhizoctonia solani), etc. The test blank was an aqueous solution containing acetone and 0.1mL/L Triton X-100.
TABLE 2 results of test for the bactericidal Activity of Compounds of formula I
The test result shows that the compound has a certain bactericidal effect on Sclerotinia sclerotiorum, alternaria wheat, pyricularia oryzae and Rhizoctonia solani at the concentration of 50 mg/L.
Claims (3)
1. A fluorine-containing pyrimidine arylamine compound has a structure shown in a formula I:
2. the use of a fluoropyrimidine aromatic amine compound as claimed in claim 1, wherein the compound of formula I is used as an agricultural or forestry pesticide having a controlling effect on agricultural pests.
3. An insecticidal composition comprising a compound of formula i as defined in claim 1 as active ingredient and an agriculturally or forestry acceptable carrier.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87103906A (en) * | 1986-06-04 | 1988-02-24 | 赫彻斯特股份公司 | The preparation of new pyrimidine derivatives and application |
| WO1992005158A1 (en) * | 1990-09-19 | 1992-04-02 | Hoechst Aktiengesellschaft | 4-anilino-pyrimidines, process for producing the same, agents containing the same and their use as fungicides |
| US5439911A (en) * | 1992-12-28 | 1995-08-08 | Shionogi & Co., Ltd. | Aminopyrimidine derivatives and their production and use |
| WO2002040473A1 (en) * | 2000-11-17 | 2002-05-23 | Ishihara Sangyo Kaisha, Ltd. | Pyrimidine compounds or salts thereof, herbicides containing the compounds or the salts, methods for control of weeds by applying the same |
-
2022
- 2022-03-31 CN CN202210368205.XA patent/CN114644596B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN87103906A (en) * | 1986-06-04 | 1988-02-24 | 赫彻斯特股份公司 | The preparation of new pyrimidine derivatives and application |
| WO1992005158A1 (en) * | 1990-09-19 | 1992-04-02 | Hoechst Aktiengesellschaft | 4-anilino-pyrimidines, process for producing the same, agents containing the same and their use as fungicides |
| US5439911A (en) * | 1992-12-28 | 1995-08-08 | Shionogi & Co., Ltd. | Aminopyrimidine derivatives and their production and use |
| WO2002040473A1 (en) * | 2000-11-17 | 2002-05-23 | Ishihara Sangyo Kaisha, Ltd. | Pyrimidine compounds or salts thereof, herbicides containing the compounds or the salts, methods for control of weeds by applying the same |
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| CN114644596A (en) | 2022-06-21 |
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