TW386019B - Insecticidally active aryl pyrimidine compounds and compositions comprising them and methods using them to control insects - Google Patents

Description

Printed by the Shellfish Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (1) Technical scope The present invention relates to an aryl group, which can be used as herbicides and pesticides at the same time. When used as a herbicide, the novel compound is particularly effective for the application of a variety of grasses and leaves of weeds before and after germination; when used as an insecticide, the novel compound was found to be particularly effective for aphids and rice planthoppers. Vulnerable and uncultivated plants-often referred to as "weeds" can reduce the yield of cultivated plants and other useful agricultural grasses through competition of cultivated crops, so weeds can interfere with seeds Growth of plants, vegetables, fruits, and leaves of trees or plants. Weeds tend to actively compete with cultivated plants for available light and space, moisture, and nutrients in the soil, leading to this aversive result. Also, those skilled in grain conservation are also familiar with a variety of commercially important food plants And plants for construction and decoration are also vulnerable to pupae caused by pests. This pest is a rather serious economic shock, especially for important cereals such as rice and corn. For this reason, there is a continuing need for improved protection of cereals composition 'to make it more effective against weeds and this pest such as insects, ticks, nematodes, and the like. In addition, the industry has a particularly extensive demand for the protection of cereals that not only does not affect the environment, but also has a satisfactory effect at a relatively low concentration, because -4 _ This paper is suitable for China National Standards (CNS) standards ^ (210X297mm) (please read the notes on the back first, write this page) Threading A7 A7 Printed by B7 of the Central Standards Bureau, Ministry of Economic Affairs and Consumer Cooperatives V. Description of the invention (2) This can be effectively controlled There is an urgent need for compounds of weeds and other pests that do not cause environmental problems. U.S. Patent Nos. 4,746,352 and 4,76,0,163-both issued to Wenger et al.-Reveal urinary urinary vinegars and their salts, which are reported to have herbicidal properties ^ issued to Steelman et al, United States Patent No. 4,280,999 further discusses "insecticide" methods using uracils. Issued to Walter Brouwer, Ethel Felauer, Paul

McDonald et al. (Three inventors of the present invention) in U.S. Patent No. 5,134,144 discloses and describes in detail some of the urinary hysteresis-bonded uracils and thioether uracils-surprisingly It has been found off-site that it has acaricidal, insecticidal and nematicidal activity at relatively low concentrations. In addition, in U.S. Patent No. 5,1; 34,145 issued to Brouwer, Felauer, and McDonald (the three of us), some other urinary bites-ester uracil bites were revealed and described in detail. We found it very poetically. It also has acaricidal, nematicidal and nematicidal activity at relatively low concentrations. Objectives of the invention The implementers of cereal protection techniques are well-known that a variety of prior art compounds have herbicidal and / or insecticidal activity ', but there has been a continuing need to identify and use more effective compounds in cereal protection domains, making them more effective Provides human benefits by controlling weeds and other pests. The present invention relates to oxoalkylated oximes of aromatic roads or longans. This novel fatty compound can be distinguished from its structure and function by the aforementioned prior art compounds. _____- 5- This paper size applies to Chinese National Standard (CNS) A4 (210X297 mm) (Please read the precautions on the reverse side first ο write this page)

C Order! A7 B7 5. Description of the invention (3) Especially the novel compound of the present invention has both herbicidal and insecticidal activities. Those skilled in the art of grain protection will better understand other aspects, features, and advantages of the present invention by referring to the following detailed description. SUMMARY OF THE INVENTION The present invention discloses a novel pyrimidinylaryl ketoxime, which has excellent herbicidal and insecticidal activities. Its herbicidal activity is particularly effective against grass plants and broad-leaved weeds, and its insecticidal properties are particularly effective against rice planthoppers and aphids. The invention also discloses a method for producing the active compound. The active compound of the present invention can be represented by formulas I, la, and lb: --------- Ά-- _, * (Please read the note on the back first to write this page). C-

R u 7 T C = NOR:

Order printed by the Consumer Cooperatives of the Central Sample Bureau of the Ministry of Economic Affairs and

C = NOR5 -6-This paper size is applicable to China National Standards (CNS) A4 (210X29 * 7mm) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs A7 B7 V. Description of the invention (4) where: R1 is hydrogen , CrCtf hydrocarbon group, hydroxyf group, alkaline earth metal, or organic base salt R2 and R6 are hydrogen, halogen, or hydrocarbon group respectively; R3 is hydrogen, halogen, cyano, nitro linear alkoxy, branched alkoxy or Cycloalkoxy, linear alkenyloxy, branched alkenyloxy or cycloassociated linear alkylthio or branched alkylthio, or hydrocarbon group 9 R4 is argon or hydrocarbon group; R5 is 2-tetrahydrofuranmethyl Or (^-(: 6 hydrocarbon group; and where R5 can be Ci_CU straight-chain alkoxy or branched alkoxy group, or trimethylsilyl group, or C "C6 nicotinyl group substituted with up to 11 southern elements Substitution; or wherein r5 may be a Re-C02-R7 group, wherein Re may be part of a Ci-Cs alkylene group and may be substituted by a Ci-Ce straight bond group or a branch bond group, or containing 1 To 6 from a prime atom; and wherein R7 may be a C ^ -Ce hydrocarbon group, or an aromatic structure group listed immediately below,

Where Re is the same as defined above; and where (R8) m is defined as follows: m is an integer from 0 to 5, and R8 may be selected from halogen, nitro, cyano, carboxyl, C, C4 alkoxy, (^-≪: 3 alkoxycarbonyl, or Cl-c4 nicotinyl, or ReCOR9 groups, where Re is the same as defined above, where 1 ^ 9 is Ci-C4 hydrocarbon group, benzene substituted with Ci-C * hydrocarbon group Base, use Cl-C4 _______- 7-_ This paper is from the standard of Zhongguanjia (CNS) A4 (210X297 mm) '-(Please read the "Notes on this page and write this page first") Order A7 B7

.11 Description of the Five 'Invention (5) Linear or branched alkoxy substituted phenyl, c ^^ un PC 4 alkyl substituted phenyl, halogen substituted phenyl, or immediately following The aromatic structure group 芳 C0 shown below is a linear alkoxy group or a branched alkoxy group, (^-<: 4 hydrocarbon group, or ionomer; and wherein X and γ are sulfur or oxygen, respectively. "Detailed description of the invention The present invention relates to novel compounds having herbicidal, insecticidal, acaricidal, and nematicidal activity, which can be expressed by the following formulas I, la, and lb: (Please read the note of $ to write this page)

, 1T if ONOR R4 5

C * NOR R ° R 5 3 CN SR1 la: Consumption cooperation of employees of the Central Bureau of Standards of the Ministry of Economic Affairs, printed CH, and: 3C N ,, X R1 NC * NOR- lb -8-This paper size is applicable to Chinese national standards (CNS) A4 specification (210X 29? Mm) Printed by the Central Standards Bureau of the Ministry of Economic Affairs, Shellfish Consumer Cooperative, A7 ______ B7 ^ _ 5. Description of the invention (6) where: R1 is argon, CrCe hydrocarbon group, methylol, toad metal Or organic base salts R2 and R6 are argon'halogen or C4C4 hydrocarbon group; R3 is hydrogen, halogen, cyano, nitro, Cl-C6 linear alkoxy, branched alkoxy or cycloalkoxy Group, Cs-C6 straight chain alkenyloxy, branched chain alkenyloxy or cycloalkenyloxy group, CrC6 straight chain alkylthio or branched chain alkylthio group, or Cl_c6 hydrocarbon group 9 R4 is argon, or C "C4 hydrocarbon group; R5 Is 2-tetrahydrofuranmethyl or 0-(: 6 hydrocarbon group; and wherein R5 can be a C4 linear alkoxy or branched alkoxy group, or a trimethylsilyl group, or a compound substituted by up to 11 atoms Ci-Ce hydrocarbyl group substitution; or wherein the anion 5 may be a Re-COrR7 group whose * Re may be part of a Ci_C3 alkylene group and may be substituted by a linear alkyl group or a branched alkyl group, or containing 1 to 6 By a prime atom; and R7 may be a Ci-C6 hydrocarbon group, or an aromatic structure group listed immediately below

Where Re is the same as defined above; and where (R8) m is defined as follows: m is an integer from 0 to 5, and R8 may be selected from halogen, nitro, cyano, carboxyl, CrC4 alkoxy, c, c3 Alkoxycarbonyl, or ci-c hydrocarbyl, or ReCOR9 groups, where Re is as defined above, 4, ο λ where R is ^. Hydrocarbyl, phenyl substituted with C, C4 hydrocarbyl, c ρ 1 C 4 _ -9- Zhongguanjia sample standard (CNS) A4 specification (210X297 mm) '------- (Please read the note of backing first ^ write this page) A7 B7 V. Description of the invention (Linear alkoxy or branched alkoxy substituted phenyl, Cl-c4 alkyl substituted phenyl, halogen substituted phenyl, or aromatics listed immediately below Family structure base-C0

The Central Bureau of Standards, Ministry of Economic Affairs, and the Consumer Cooperation Du printed equipment, where linear or branched alkoxy, CrQ hydrocarbyl, or halogen; and where X and γ are sulfur or oxygen, respectively. The term & preferred embodiment "hydrocarbyl" refers to the saturated or unsaturated portion of a linear, branched or ring system containing only hydrogen and carbon atoms. Generally, it is found that the biologically active compounds of the present invention have the structure of the above formulae j, la and lb, wherein: Ri is hydrogen or Ci_C3 alkyl; R2 is hydrogen; R3 is fluorene, sulfonium, or C! -C3 alkyl R4 is gas; r5 is (^ to € 4 alkyl; R6 is argon; and X and Y are both oxygen. In other cases, it is found that the biologically active compound of the invention has the above formula I, Ia and lb Structure, where iR1 is methyl; R2 is hydrogen; R3 is hydrogen or methyl; R4 is hydrogen; R5 is methyl, ethyl, third butyl or isopropyl; R6 is fluorene; and X and γ are all More specifically, the novel biologically active compounds have been found to be particularly effective herbicides when R1 is argon, methyl or ethyl; when anaerobic 2 is hydrogen or methyl; when R3 is tritium, gas or methyl When R4 is hydrogen or f group; # R5 is shown in the following table I; when R6 is argon or methyl; when X is oxygen or sulfur; and when γ is oxygen or sulfur. Similarly, the biologically active compound is found when Achieving the above redefinition -10 · This paper size is applicable to the Chinese National Standard (CNS) Α4 size (210X297 mm) 1 (Please read the precautions on the back first ^ write this page),? Τ

/ X Produced by Shelley Consumer Cooperation of the Central Bureau of Standards, Ministry of Economic Affairs, printed A7 B7 5. The chemical structure standard of invention description (8) can be used as a particularly effective pesticide. In a broader aspect of the pesticide composition, the present invention relates to a novel herbicidal, insecticidal, acaricidal, and nematicidal composition (hereinafter collectively referred to as "pesticidal composition"). The pesticide composition includes : (A) Structural formula I, Ia & lb compound poplar as shown above and defined with the dose of the pesticide; and (B) appropriate carriers for them. Industrial Applicability Another aspect of the present invention relates to a process or method for controlling the amount of objectionable weeds, insects, mites and nematodes using the structural formulae, la and lb compounds as shown and defined above. This method includes applying to a preselected place or site a composition comprising the following effective pesticide doses: (A) compounds of structural formulae I, u, and Ib as shown and defined above for the effective pesticide dose; and (B ) For their appropriate vehicle. Synthetic method Another aspect of the present invention relates to a process or method for preparing the compounds of the structural formula I, la and lb as shown above, wherein ... to rule 6 and X and γ are as defined above. In particular, the compounds represented by the following structural formula II can be easily produced by synthetic processes or methods familiar in the literature. In fact, such methods are similar to the synthetic steps shown in our U.S. Patent Nos. 5,134,144 and 5,134,145- --11-This paper size is applicable to China National Standard (CNS) A4 (210X297mm) (Please read this page first to write this page) *,-= *

A7 B7 V. Description of the invention (9) As mentioned above, both of them briefly mentioned how β produces β-ketoesters (the following formula II), the starting materials, and react with ammonia gas to form enamines (the following formula III ), The sodium (formula IV below) is prepared by adding amines (formula III below) to a suspension of sodium hydride in a suitable solvent such as tetrahydrofuran or dimethylformamide. ΝΗ, Μ, Η CF3C0CH2C (0) 0C2H5 —► CF3C (NH2) «CHC (0) 0C2H5 —► N» HN-C-CH-C (0) 0CjH5 CF, (M, (" I) (IV) In addition, it is prepared by reacting a suitable aromatic amine (formula V below) with phosgene or thiophosgene in a suitable solvent such as methane, ethyl acetate, toluene, xylene or any aprotic solvent familiar in the art. Into isocyanates and isothiocyanates. V 1 ((Please read the note of back ^^ write this page first)

, 1T

(V) (VI) Printed by the Central Bureau of Standards, Ministry of Economic Affairs, Consumer Cooperatives. In (V) and (VI) above, the Qi part is used to explain the replacement position of the aromatic ring of the structural formula shown. The compounds of the present invention can be easily obtained by appropriate sodium salts of the enamines (formula ¥) at relatively low temperatures, usually -5 (TC to -7 Ό Ό) in an inert solvent such as tetrahydrofuran or diamine. Methyl methylamine is produced by reacting with isocyanate or isothiocyanate (Structural Formula VI) and allowing the reaction to reach ambient temperature (25 Ό) over a period of several hours. ____ -12- This paper size is applicable to Chinese national standards (CNS > A4 size (210x297 mm) A7 B7 printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 5. Description of the invention (10) The pyrimidine obtained by the following formula (the following formula Γ), where R1 in this case is only Na (Na) and y is oxygen, which can be easily separated later, first remove the solvent, then dissolve the residual mixture in water, and then acidify the so-dissolved residue with a shovel mineral acid such as hydrogen acid, soul acid, phosphoric acid or nitric acid. Into the formula T, where R1 is hydrogen.

N «HN-C» CH-C (0) 0CjH5 ♦ XCN IV) Organic phosphonium salts can be prepared by treating compounds I, la, and lb (where R1 is hydrogen) with the chemical formula R'R''R ”'N Easily made, wherein: the R ,, R "and R '" groups are fluorene or a hydrocarbon group or a hydroxyalkyl group or a mixture thereof, containing 3 to 48 atoms; or two or three R ,, R ,,, and R "'groups are combined to form basic gas-containing male rings (eg, bite, morphine, hexahydroe-bite, etc.), and the remaining groups or radicals-if any The word _ is hydrogen; the treatment is performed by using a suitable solvent such as ethanol, tetrahydrofuran, etc. In general, the organic eyelid must have sufficient strength to form salts, that is, the detected pKa 値 must be greater than about 4.85 ^ Solvent removal Then, the organic salts of the compounds of the present invention are left, a kind of the organic magnetic 'M can be represented by Structural Formula 1 (described below), except for the position occupied by the R1 portion of Structural Formula I (only in the The situation under discussion ______ -13- The paper size is in accordance with the Chinese National Standard (CNS) A4 specification (2 丨 0X297 male *) (Please read 4-note on the back ^ write this page )

NOR5

(VI Ding

I A7 * ~ ------ B7______ 5. The invention description (U)) is an orbit containing free-state electrons, which make the connected nitrogen atom negatively charged, and γ is oxygen:

HNR * R_ * R ... In the case where the R1 part of the present invention is an alkyl group, such compounds can be easily prepared by methods well known in the literature. For example, when starting from a compound of formula I, where R1 is argon, in the presence of a suitable test such as carbonic acid, I »bito, trihexylamine, treat with decanes or alkyl sulfates in a suitable solvent. , N-calcined product can be obtained. With the exception of these compounds where X is sulfur, S-alkylated compounds of formula la can be prepared using this alkylation step. (Please read the notes on the back to write this page)

Printed by Shellfish Consumer Co-operation, Central Bureau of Standards, Ministry of Economic Affairs, where R1 to R6 and Y have been described previously. As mentioned above, the pesticide composition of the present invention contains a carrier as one of the ingredients, and the carrier is suitable for mixing with the active ingredient of the present invention: that is, a compound having Formula 1, Ia, and Ib. Carriers and forms suitable for the purpose of the present invention can be selected from the following. -14- ______ This paper size is applicable to China National Standard (CNS) A4 (210x297 mm) _____B7__ 5. Description of the invention (12) In some applications, a suitable carrier can be finely divided particles of pulverized solid particles, Granular or pellet form, or in the form of a wettable powder, a flowable liquid, a soluble powder; in other applications, the carrier can be an aqueous or organic solvent, an aqueous or organic dispersion, or an aqueous Forms of organic emulsifiers 0 They are familiar with the substances that can be used in the manufacture of complex solid carriers (such as pellets, granules, wettable powders, soluble powders, other micro-divided particles, etc.) Commercially available materials such as American activated clay, sand, vermiculite, corn cob, activated carbon, and mineral silicas, among the mineral silicas are mica, talc, pyrophyllite and the like. When the carrier is a solid, a biologically active solid composition can be easily prepared using the active ingredient of the present invention. For example, the active ingredient can be injected into the solid carrier by methods well known to those skilled in the art. An alternative method is to formulate the active ingredient of the present invention into a fullerable powder 'by grinding the active ingredient in the form of a compound to a fine powder' and then mix the obtained powder with a suitable surface-active dispersant beforehand. Appropriate solid carriers are mixed or combined. The printable bag of the Shellfish Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs then dispersed the obtained wettable powder in water and sprayed it on the soil surface, the cereals to be protected, and / or the weeds. When the carrier is a liquid, the active ingredient of the present invention can be used to easily prepare a biologically active liquid composition ', especially a liquid solution as a representative of a preferred embodiment of such a liquid composition. In the case of a liquid solution, the active compound can be easily dissolved in a suitable aqueous or organic solvent as is well known to those skilled in the art. ___________ * 15-This paper size is applicable to China National Standard (CNS) A4 (210X297 mm) A ~~~~ A7 —___ B7 V. Description of the invention (13) The preferred solvent used in the present invention is aromatic or Aliphatic hydrocarbons, toluene in hydrocarbons are particularly suitable. However, within the scope of the present invention, liquid emulsions are often used more often than liquid solutions. Emulsions are preferred because other compounds with I or 1 & are so-called "organic" compounds. Accordingly, the biologically active formulation containing the active ingredient of the present invention will-most likely-use the largest and most cost-effective carrier known to humans: water. For their and other reasons, water is the preferred vehicle. Preparation of biologically active formulations containing water as the main ingredient (including the active ingredient of the present invention), the active ingredient of the present invention in an appropriate form can be easily dissolved in a suitable organic solvent previously added with a suitable surface-active dispersant, usually thereafter Water is then added to (in addition to or in combination with) the resulting mixture to form an aqueous emulsion. The resulting aqueous emulsion can be easily applied to a specific location ("place") to be protected. A particularly suitable application method is spraying. Sprinkle. The emulsion may alternatively use an organic liquid such as an oil as a dispersant. The surface-active dispersant can be any example of a surface-active dispersant suitable for the purpose of the present invention, which is well-known to those skilled in the art, and is listed in the North American version of Mc C utche ο η 's 1 9 9 3 Emulsifiers & Detergents (Volume One) 275-297 pages, and international version of McCutcheoWs 1993

Emulsifiers & Detergents (Vol. 1) 247-268 and 271 pages, both of which are M. C. Publishing Co. (Me Cute he on

Division) of Glen Rock, New Jersey. _______- 16 -__ This paper size applies to China National Standard (CNS) A4 (210X297 mm) '(Please read the notes on the back _

Ordered by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs. Printed by the Consumer Standards of the Central Standards Bureau of the Ministry of Economic Affairs. Printed by A7 B7. Plant and pest methods (including mites and nematodes). Specifically, this method is more suitable for applying effective doses of biologically active ingredients having structural formulas I, 3, and 115 to a pre-selected place (ie, "place"). For the novel biologically active ingredients of the present invention, R1, R2, The r3, r4, R5 and R6 portions are as described above. As mentioned above, the biologically active ingredient of the present invention can be combined with a carrier for the purpose of preparing a special formulation, and then applied to a specific place. In many applications using the biologically active ingredients of the present invention, the concentration or weight% of active ingredients in effective pesticide formulations ranges from about 1 to about 95% by weight of active ingredients in the formulation, based on the total weight. In a preferred embodiment of the present invention, the novel biologically active ingredient is combined with a suitable carrier, and then formulated into a herbicidal emulsion. The concentration or weight% of the active ingredient in the emulsion is about 0 ·. 0.02 to about weight percent, based on the total weight of the formulation. Specifically, when compounds of structural formulae I, Ia, and Ib are used as pre-emergent herbicides, this use includes the application of about 0.01 kg (0022 pounds) to about 10 kg (22 pounds) of novel Bioactive ingredients (ie about 0.022 kg to about 25 kg per hectare). When using a pre-emergent herbicide, the herbicide is usually applied to soil that contains not only weeds but also the desired cereal seeds. This application is applied to the soil surface or below the soil surface 2-5 cm to 7.5 cm (1 to 3 inches) )depth. In the case of using the novel biologically active ingredient of the present invention in the weed germination ("post-emergent herbicide"), the biologically active ingredient (having the structural formula j ___ -17- This paper is applicable to the Chinese National Standards (CNS) Eight 4% divisions (210X297 mm)-1 —I n I---- Table ——. I -m Γ. L (please read this note on the back to write this page) Order A7 B7 Central Bureau of Standards, Ministry of Economic Affairs Printed by the Consumers' Cooperative Cooperative V. Description of the Invention (15), la and lb) The dosage is similar to 0.01 kg (0022 lbs) to ι0 kg (22 lbs) per acre (about 0.00 per hectare). 2 2 to about 2 5 kg). Post-emergence applications can be done by spraying nasty plants from the ground or from the air. But those skilled in the art will understand that in any particular formulation, the weight% or concentration of the novel bioactive ingredient is determined by a number of factors including ( But not limited to) soil type, soil pH, soil organic matter content, rainfall and density before and after treatment, air and soil temperature, daily light intensity and light period, when the biologically active compound of the present invention is used for weed control All of these factors have an effect on their effectiveness. However, those skilled in the art can easily determine the optimal conditions for using the new biologically active compounds covered by the present invention through routine experimentation. The following examples are only used to illustrate the scope of the present invention. In one point, the scope of the present invention must not be limited by the following examples. Example 1: 3- [3,6-dihydro-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] benzaldehyde 0-l-ethyl ethyloxime ( Compound No. 5> Example 1 (Compound No. 5) was prepared using the following steps. Step 1: 3-Nitrobenzaldehyde (30.2 g, 0_2 mol), potassium carbonate (25 g), and dimethoxyethyl Gasification in alkane (400 ml). Methyl ethyl hydroxyl ammonium (25 g) was combined in a reactor, followed by stirring and refluxing for 5 hours, cooling, and leaving overnight. After removing part of the solvent, water was added The product was extracted into methane gas, and the solution was washed twice: first with saturated sodium sulfite, and then with water. • 18-This paper size applies to the Chinese national sample (CMS > A4 size (210X297 mm)) {Please read the note on the back first to write this page).-Order the seal A 7 __B7__ of the Consumer Cooperatives of the Central Rubbing Bureau of the Ministry of Economic Affairs. 5. Description of the invention (16); After drying and evaporation, 27 grams of Brown oil, which was determined to be 3-nitrobenzaldehyde 0-methylethyloxime. Step 2: Use Parr hydrogenator with 5% Pt / C (0.8 g) as catalyst (200 ml) of the above crude product was reduced, and after removing the catalyst, the solvent was removed and the residual oil was purified by silica gel chromatography with digas methane. The resulting 20 g (0.11 mole) of the product (an oil) was determined as 3-aminobenzaldehyde 0- 1-methylethyl bow. Step 3: Secondly saturate the above amine in anhydrous ethyl acetate (150 ml) with hydrogen acid gas until the hydrogenated salt stops precipitation. Stir and heat, then After the introduction of phosgene, the reaction was uniform within 10 minutes, and the solvent was removed after 30 minutes of passing in the phosgene. After the solvent was removed, 24 grams of oil remained, and the oil was determined to be 3 isocyano. Benzaldehyde-0- 1 -methyl ethyl rib. Step 4: Wash sodium hydride (4.4 g, 60 〇 / 〇, 0.11 mol) with petroleum ether first, then add anhydrous THF (200 ml), stir and cool with ice In the case of a solution of ethyl 3-amino-4,4,4-trifluoro-2-butyric acid (20 g) in tetrahydrocran (50 ml) was added dropwise for 1 hour, stirring was continued After 30 minutes, it was cooled to -70 ° C, and then the isopropyl ester in 25 ml of THF (step 3 ) Add quickly. Keep the reaction mixture at -7 0 ° C for 2 hours, then allow it to reach ambient temperature (ca. 25 ° C) and allow to stand overnight. Remove the solvent and add water (100 ml), using methane gas. Washed three times and acidified, the precipitate was extracted into methane, washed with water, and dried ____- 19-_ -_ This paper is in accordance with China National Standards (CNS> A4 (210X297)) (1) Please read the notes on the back page and write this page)-: '· This book is printed in A7 B7 printed by the Central Ministry of Economic Affairs, Central Bureau of Work, Consumer Cooperatives. 5. Description of the invention (17) and evaporation. The crude material was recrystallized from a toluene / cyclohexane solvent to obtain (13 g) of benzaldehyde, 3- [3,6-dihydro-2,6-dioxo-4- (trifluoromethyl) -1 (211 ) -Pyrimidinyl]-, 0-1 -methyl ethyl bow, its boiling point ("m.p., ') was determined to be 1 8 1 -1 8 3 * C. Other analytical data include the following: C, 52.59; H, 4.05; N, 12.34; C14H14F3N303 requires C, 52 · 57; Hf, 4.11; N, 12.32 »Example 2: 5- 丨 3,6-diargon-2,6-dioxy-4- (three Fluoromethyl) -1 (2H) · pyrimidinyl] -2-methylbenzaldehyde 0-methyl fat (Compound No. 20) Example 2 (Compound No. 20) was prepared using the following procedure. Step soil 1 : Manufacturing 2-methyl-5-nitrobenzaldehyde according to the procedure stated in Journal of Medicinal Chemistry, Vol. 31, No. 1, 138-144 published in 1988. Gasified hydroxylammonium (10 g) and The triethylamine (20 ml) of acetic acid (100 ml) and the aldehyde (20 g, 0.12 mol) thus produced were refluxed for 2 hours. After cooling, most of the solvent was removed and water was added, and the coarse ribs precipitated out. And collected on filter paper, washed with water followed by drying, resulting in 14 g of boiling point 133-1 A yellow-brown solid at 36 ° C was determined to be 2-methylnitrobenzaldehyde B. Step 2: The rib (M g, 0.1 mol) contains excess methyl iodide (5 ml) and potassium carbonate (11 G) Mix in 60 ml of N, N-dimethylacetamide for 60 hours. Afterwards, pour the reactants into water, the cream-colored solids are separated and collected at -20. Standard (CNS > A4 size (210X297mm) JMm% (Please read the note on the back to write this page) Γ A7 B7___ V. Description of the invention (is) on the filter paper, wash with water and then dry. Then from ethanol Recrystallization gave a cream-colored solid with a boiling point of 〇OO-ΐ0 3 t. The cream-colored solid was determined to be 2-methyl-5 -nitrobenzaldehyde, 〇methyl M. Steps 3 and 4 : In addition to isolating the argon gas of aniline and drying it before conversion to an isocyanate analog, the M is reduced according to the method stated in steps 2 and 3 in Example 1 and then converted to an isocyanate analog. Step 5 •• Similar to the method stated in step 4 in Example 1, with a boiling point of 1 9 1 -1 9 2 ° C White solid (7.8 g), determined to be 5- [3,6-dihydro-2,6-dioxo-4- (trifluoromethyl) -1 (211) -pyrimidinyl] -2-methyl Benzaldehyde 0-methyloxime. Dihydro-6-oxo-2-thioketo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] benzaldehyde 0-methyl bowel (Compound No. 18 ) Example 3 (Compound No. 18) was prepared using the following procedure. Step 1: Reduction of 3-nitrobenzaldehyde O-methyl ribs (15 g, 0.83 moles) in a Parr argonizer according to the method stated in step 2 of Example 1. Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs (please read the notes on the back to write this page). Then use the crude product (10.6 g, 0.78 mol) in dichloromethane (50 ml) with ice (85 G). Stir and add dropwise thiophosgene (6.5 ml) in the second gas (15 ml). After stirring overnight, the resulting organic composition was separated, washed with water, then dried and evaporated to give 16 g of a yellow oil, which was determined to be 3-isothiocyanobenzaldehyde 0-methyloxime. Step 2: Use the same method as stated in step 4 in Example 1 to convert the isothiocyanate derivative into 10 g of a yellow solid with a boiling point of 195-197 X: ___- 21 -___ This paper size applies to Chinese national samples Standard (CNS) A4 (210X297 mm) " ~ " Work and Consumer Cooperation Duty Packing A7 B7, Central Bureau of Standards, Ministry of Economic Affairs 5. Description of the Invention (19), which is determined to be the following uracil: 3-[ 3,6-dihydro-6-oxo-2-thioketo-4- (trifluoromethyl) -1 (2Η) · pyrimidinyl] benzaldehyde 0-methyloxime. Other analytical data include the following: C, 47.72; Η, 3.01; N, 12.67, C13H10F3N3O2S requires C, 47.42; Η, 3.04; Ν, 12.77. Example 4: 3- [3,6-Diargon-2,6-dithioketo-4- (trifluoromethyl) -1 (2Η) -pyrimidinyl] benzaldehyde 0-methyl rib No. 24) Example 4 (Compound No. 24) was prepared using the following procedure. The product from Example 3 (3 g, 9.1 mmol) in toluene (30 ml) was treated with Lawesson 4s reagent (3 g) on the first day and refluxed for 4.5 hours on the second day Add another 5 hours. After removing the precipitated solids, the filtrate was evaporated, and the residue was then recrystallized from a minimum amount of toluene. The resulting product was a red solid with a boiling point of 196-198 ° C. Other analysis data include the following: C, 4 5.5 7; Η, 2.90; N, 11.83, C13H1 () F3N3OS2 Requirement is C, 45 · 20; Η, 2.91; Ν, 1 2. 1 6 ° * Manufacture and use of Luo The procedure statement of Sen's reagent is published in 1985, Tetrahedron Report Number 192, V ο 1. 41, No. 22, 5061-5087, printed in the United Kingdom. Example 5: 3- [3,6-Diargon-2-oxo-6-thioketo- 4- (trifluoromethyl). 1 (2H) · pyrimidinyl] benzaldehyde 0-2 -propenyl Ribs (Compound No. 22) Example 5 (Compound No. 22) was prepared using the following procedure. 3- [3,6-dihydro-2,6-dioxo-4- (trifluoromethyl) -1 (2Η) -pyrimidinyl] -22- This paper is again suitable for China National Standard (CNS) A4 Specifications (210X297mm) if ϋ (please read the notes on the back to fill in this X) * Cloths--Printed by the Central Government of the Ministry of Economic Affairs, Shellfish Consumer Cooperatives, printed A7 B7 V. Description of the invention (2〇) Benzaldehyde 0- 2-propenyl oxime (7.8 g, 24 mmol) was combined with Rosen's reagent (8 g) in toluene (100 ml), and then refluxed for 10 hours. After removing the solvent, a red gum was produced, which was then purified by silica gel chromatography with a 40:60 weight ratio of ethyl acetate: hexane. A red oil was obtained, which gave 6 g of product from a toluene / cyclohexane solvent. Repeated column elution with dichloromethane gave a relatively more purified product. Recrystallization from a toluene / cyclohexane solvent gave 3.1 g of a red solid with a boiling point of 169-171 ° C. Example 6: 2-Gas-5- [3,6-diaza-2,6 · dioxo-3-methyl- 4- (trigasmethyl) -1 (2Η) -pyrimidinyl] benzaldehyde 0- 1-Methyl Ethyl Fatty Compound (Compound No. 4) Example 6 (Compound No. 4) was prepared using the following steps. Step 1: 2-Gas-5-nitrobenzaldehyde in dimethoxyethane (100 ml) Mix with 0-methyl ethylammonium chloride (11.1 g, 0.1 mole) and carbonic acid (1 3.4 g), stir and reflux for 2.5 hours. After pouring into water, the precipitated solid was extracted into digas methane, washed twice with saturated sodium bisulfite, then washed with water, dried and evaporated, leaving a solid (20 g) of 2-gas-5- Nitrobenzaldehyde 0-methylethyl rib. Step 2: The above-mentioned fatty ether (12 g, 0.05 mole) in ethanol (200 ml) was reduced in a Parr hydrogenator using 5% by weight 卩 (: (0.7 g) as a catalyst. Filtration After the solution was obtained, the solvent was removed, and the residual oil was eluted and chromatographed with digas methane in a short column silica gel tube. After removing the eluent, 10 g of pale yellow oil was obtained. The residue was analyzed ___ 23 _ paper Standards are applicable to China National Standards (CNS) Α4 specifications (210X297 public shame) '---------- τι-- • *! Γ (Please read the notes on the back first, fill out this page) Order the Ministry of Economic Affairs The Central Government Bureau of Work Preparatory Work and Consumption Cooperation Du printed A7 B7 5. The description of the invention (21) is 5-amino-2 -gas benzaldehyde 0_1 · methyl ethyl oxime. Step 1: Then use gasified hydrogen to make The amine (step 2 above) was saturated in anhydrous ethyl acetate (100 ml), and the hydrogenated salt of aniline remained in the solution. This solution was treated with phosgene for 1.5 hours under reflux. After filtration, The reaction mixture was aspirated and then the solvent was removed to obtain an ochre oil (9.5 g), which was used directly in the following steps. Sodium hydride (2 g, 0.05 mole) washed with oil ether was suspended in THF (100 ml) and cooled in ice, and 3_amino_4'4,4-digas-2-butanoic acid ethyl was stirred under stirring Tooth (7.4 g, 0.04 mol) of tetragas sulfan (25 ml) solution was added dropwise and kept in the ice bath for 1 hour. The reaction mixture was then cooled to _7 0t in acetone / dry ice. Then, add the isocyanin derivative in THF (25 ml) (step 3 above). Before removing the ice bath, keep the ice bath temperature at -7 (TC for an additional 2 hours. The reaction mixture is then allowed to reach the environment. Temperature (ca. 2 5. (:), and left overnight under ambient conditions. The THF solvent was removed, the residue was dissolved in water, washed three times with methane gas and acidified. The separated oil was extracted into methane gas. After washing with water, drying and evaporation, a yellow solid was produced and subsequently washed with isopropanol, leaving 3 grams of the substance and found to have a boiling point of 193-194 ° C. The residue left after the evaporation of isopropanol was from toluene / Cyclohexane solvent recrystallization _____- 24- This paper size applies to China National Standard (CNS) A4 210X297 mm) i teeth (please read the notes on the back ^ 0 to fill out this page) Γ Seal of the Consumer Cooperatives of the Central Government Bureau of the Ministry of Economic Affairs Α7 Β7 V. Description of the invention (22), get 2.7 grams of 2 Qi-5 -3- [3,6-dihydro-2,6-dioxo-3-methyl- 4- (trifluoromethyl) -1 (2Η) -pyrimidinyl] benzaldehyde It is found that its boiling point is 191-193 ° C (Other analysis data of the above-mentioned solids of the second "class" include the following: C, 47.74; H, 3.49; N, 11.16, C15H13C1F3N3 03 The requirement is C, 48.00; Η, 3.47; N, 11.20. Step 5: Dissolve the mixture containing potassium carbonate (3.5 g), tetrabutylammonium iodide (0.5 g) and methyl iodide (5 ml) into the uracil-containing (step 4 above) by stirring overnight (3.5 G) of methyl ethyl ketone (40 ml). Water was added to extract the product into methane gas. The extract was washed with water, dried and evaporated to leave a solid, which was recrystallized from cyclohexane / petroleum ether. The product obtained was 2 gas-5- [3, 6-Diargon-2,6-dioxo-3-methyl-4- (trifluoromethyl) -1 (2Η) · pyrimidinyl] benzaldehyde 0-methylmethyl rib (3 g), its solution The point was determined to be 100-10 ° C.

Other analytical data include the following: C, 49 51_, h, 3.9H 10.71, C16H15ClF3N3O3 requires c, 49.36; Η, 3.86; Ν, 1 0 · 80. Examples 7 to 2 4 Table 1 (below) lists structural formulas! Some structural data of various parts of the bioactive compounds of the present invention, Ia & Ib (above). Forty-two (42) compounds are listed in Table I below. The structural data are listed in Table I / these are #from the use of infrared light (IR ·) spectral data, and / or nuclear magnetic resonance spectral data using the Chinese state (210χ2 ^ γ ------ -.ml I--i -I- i .....-- n HI · I '' ^ / V tPlease read the notes on the back o fill in this 苋) Order A7 B7 V. Description of the invention (23 ) Qualitative and / or quantitative analysis based on and / or elements (such as C, η and N). Examples 7 to 24 (the compounds numbered 13, 6-17, 19, 21 and 23 in Table 1 below) are based on the examples above! Prepared by the method set forth in 6. Other compounds prepared (compound numbers 4, 5, 18, 202, and 24) are also listed in Table I below. Analytical data All compounds listed in Table I are found to be solid at room temperature (ca 25 ^), and Table I also includes several characteristic melting points of their different compounds ("m · p · ,,) ， W clothing-* (Jing Xian first read the note on the back ^ fill out this page) Order the Central Consumers Bureau of the Ministry of Economic Affairs to print the standard bidder 26 cm 7 29

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7 B V. Description of the invention (24) Printed by the Consumer Cooperatives of the Central Bureau of Samples, Ministry of Economic Affairs I Compound No. R 'R7 R3 R4 R5 R * X y Melting point rc) 1 Η H Cl H CH (CH3) 2 H 0 0 191-193 2 Η H Cl H CHj H 0 0 198-200 3 CH3 H Cl H ch3 H 0 0 14M42 4 ch3 H Cl H CHICHI H 0 0 100.101 5 Η HHH CHICH,), H 0 0 181-183 6 ch3 H Cl HC (CH3) 3 H 0 0 98-99 7 Η H Cl HC (CH3) 3 H 0 0 168-170 8 CHjCH3 H Cl H CHICHI H 0 0 120 121 9 CH, H Cl H CH (CH3), H 0 0 124-125 10 HH Cl H CH3 H s 0 167-170 11 CH3 H Cl H ch3 H-0 145,146 12 HH Cl H CH (CH3) j H s 0 183.184 13 ch3 H 1 Cl fr CH (CH3) 2 H 1 0 97-98 14 ch3 H Cl H 7 ch2ch2ch3 H 0 s 126.127 15 ch3 H Cl H ch, ch, ch3 H 0 0 89-90 16. HH Cl H ch2ch2ch3 H 0 0 225.227 17 HHHH ch3 H s 0 201-202 18 HHHH ch3 H s 0 195-197 19 HHHH ch2ch_ch2 H 0 0 138-140 20 HH ch3 H CH, H 0 0 191.192 21 HHHHC (CH3) 3 H 0 0 175-177 -27- ---- -----: Clothing--Λίν (Clear ^ Read the f-face notes, fill out this page) The size of the paper is applicable to China National Standard (CNS) A4 210X297 mm)

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7 B V. Description of the invention (25) Consumption cooperation by employees of the Central Bureau of Standards, Ministry of Economic Affairs, Table I Compound No. R, R2 R3 R4 R5 Rs XY Melting point (t) 22 Η Η Η Η CHjCH-CH2 H 0 s 169-171 23 Η Η Η Η CHjCH] H 0 0 183.184 24 Η Η Η Η CH, H ss 196.198 25 Η Η Η ch2c »ch H 0 0 176-178 26 Η Η Η Η ch2cic-ch2 H 0 0 139-141 27 Η Η Η ch3 CH (CH3) 2 H 0 0 183 * 184 28 Η Η Η Η ch2co2c2h5 H 0 0 148-151 29 Η Η Η Η ch2c6h5 H 0 0 196-198 30 Η Η Η Η C5H9 (CYCL0) H 0 0 191-193 31 Η Η ch3 ^ Η ch3 H 0 s 177178 32 Η Η Η Η ch2ch2f H 0 0 187 * 188 33 Η Η Η Η CH, CHjF H 0 s 167-169 34 Η Η ch3 CH, CHj H 0 0 151-153 35 Η Η Η ch2ch2ch3 H 0 0 153-154 36 36 Η Η Η T, H 0 0 185-190 37 Η Η ^ Η Η CHjCH-CHCI H 0 0 160.162 38 Η Η Η Η ch3 ch3 0 0 159 * 160 39 Η Η Η Η TZ / H 0 0 156.158 40 Η ch3 Η Η ch3 H 0 0 176178 41 Η Η Η Η ch3 H 0 0 232-233-^ 1 *-1 C (Please read the meeting first Note: Fill in this page, νδ This paper size is applicable to Chinese national standards (CN S) A4 specification (210X297 mm) A7 B7 V. Description of the invention (26) Table I Compound No. R 'R2 R3 R4 R5 Re XY welding (* c) 42 CH, Η Η Η ch3 H 0 I— " 0 158-159 Note to Table I: (1) ΙΆ CH. I, \\, 〇 /, co2c2H5 (Please read the first and foremost considerations ο fill out this purchase) Central Consumerism Bureau, Ministry of Economic Affairs, employee consumption cooperation (2) Ding 2 is CH2 (3) Compounds 1-10, 12 and 14.40 in Table 1 (above) are based on Formula I below. (4) Compounds 11 and 13 are based on Formula 1 & below, and compounds 41-42 are based on Formula Ib below.

C «NOR ·

C * NOR * • 29 · This paper size applies to China National Standard (CNS) A4 (210X297 mm)

(lb) A7 B7 V. Explanation of the invention (π) R3 C «NOR5 Example 25: Preparation of insecticidal composition Each compound numbered 1 to 42 forms a unique biologically active composition 'Steps used to complete this result The sample can be summarized as follows. First, for 42 compounds each, we dissolved 0.33 grams of each compound in 10 ml of propylamine. Each resulting solution was then diluted with 90 ml of water, and 4 drops of ethoxylated sorbitan monolaurate, a wetting agent, were added to produce a solution of 3,000 ppm. Other compositions-having 1,000, Races of 500, 200, and 100 ppm (based on the weight of the biologically active ingredient were prepared by diluting the solution with water several times from 3,000 ppm. Example 26: Test of rice planthopper leaf Each compound, a single pot containing about 20 Mars seedlings, was sprayed with a specific formulation at an active concentration of 1,000 ppm (for each of the 42 compounds) by a spray sprayer. One day after the treatment Cover each pot of plants with a thin layer cage, and transfer 20 mature rice planthoppers to each cage. Repeat this treatment without applying the active compound as a control. -30- This paper size applies Chinese national standards (CNS ) A4 size (210X29 * 7mm) ΊΙ ..- J-. II ... n ί I m ^^ 1 1 衣 --n * (Please £ -Read #-面 的 NOTES ^ / ^ Writing Page) Ordered by the Consumer Standards Cooperative of the Central Bureau of Standards, Ministry of Economic Affairs, printed A7

Employees' cooperatives of the Central Economic and Technical Bureau of the Ministry of Economic Affairs of the People's Republic of China, but this control includes the deployment of 20 mature rice planthoppers on the control rice seedling plants. Five days after the transplantation, the survival number of planthoppers in each pot was calculated, and the control 値 0 / 〇 was estimated based on the well-established test procedures in this technique. The test results of rice planthoppers ("r P Η ',") are listed in Table 2 below. Example 27 7: Rice planthopper system tests are listed in 9 specific test formulations out of 42 compounds in Table I. 〇1 g of the test compound was dissolved in 5 ml of propidium and 45 ml of distilled water and 2 drops of ethoxylated sorbitan monolaurate were formulated to a concentration of 200 ρρπι. Using a hypodermic needle and syringe, 25 ml of Each test solution was poured into the root area of each pot, and each pot contained about 475 grams of moist soil. The concentration of each test compound in the obtained soil was 10 ppm. Soil concentration ("ppmsc '"). When treated, each pot contained About 20 Martian rice seedlings were planted eight days after the seeds germinated. One day after the treatment ', each pot of plants was covered with panconofluoride and 10 mature rice planthoppers were transferred to each cage. Five days after the transplantation, the number of planthopper survival in each pot was calculated, and the adjusted control was calculated using the * Abbott's formula (Abbott's formu | a). * The procedures using Albert's formula and calculations are described in j0llrnal of Economic Entomology, Vol. 18, page 265.267. The test results are expressed as the adjusted control percentage of rice planthopper ("R ρ Η") and are listed in Table II below. ____ -31- This paper size applies to China National Standards (CNS) Α4 size (210X297 male thin) '----------- ▼--ί. (Please read the notes on the back first ο fill in (This page) *? Τ V. Description of the invention (29) Printed by the staff of the Central Bureau of Standards of the Ministry of Economy

Table II Compound No. RPH (leaf) RPH (system) SCR GPA 1 90 100 60 100 2 100 87 0 100 3 PT NT 20 NT 4 PT NT 20 NT 5 100 100 0 100 6 0 NT 100 NT 7 0 NT 0 NT 8 0 NT 0 NT 9 0 NT 0 NT 10 80 · < NT > 6 NT 11 0 NT 0 NT 12 80 NT 0 NT -32- This paper size applies to the Chinese National Standard (CNS) Α4 specification (210 × 297 mm) ^^^^ 1 nn — ^^ 1 m ^ i ^^^^ 1 ^ ϋ nn, * / V (Please read # 面 之 NOTICE to fill out this page)

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7 B V. Description of the invention (50.) Consumer cooperation of the Central Bureau of Standards of the Ministry of Economic Affairs, printed form II Compound No. RPH (leaf) RPH (system) SCR GPA 13 0 NT 0 NT 14 0 NT 0 NT 15 0 NT 0 NT 16 0 NT 0 NT 17 100 NT 16 100 18 0 NT 0 NT 19-100 NT 58 99 20 100 100 0 100 21 70 NT 0 NT 22 100 NT 0 40 23 100 100 0 100 24 70 NT 0 NT 25 100, 100 0 100 26 PT 1 NT 11 NT 27 0 NT 0 NT 28 0 NT 0 NT 29 0 NT 0 NT 30 0 NT 11 NT 31 100 100 0 99 _i i I i I----I- I ... I ........ it, ...... HI * (please ^: read the notes on the back ^, fill in this page) The size of the paper is applicable to China National Standard (CNS) A4 (210XW7) C) Μ

B V. Description of Invention (51) Printed by the Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs

Table II Compound number RPH (leaf) RPH (system> SCR GPA 32 100 100 11 100 33 100 100 0 100 34 0 NT 0 NT 35 0 NT 0 NT 36 0 NT 0 NT 37 98 NT 0 90 38 0 NT 11 NT 39 0 NT 0 NT 40 PT, NT 100 NT 41 80 NT 16 NT 42 0 NT 16 NT Note to Table II: (1) "PT" means that the test compound was found to be completely phytotoxic at the evaluation rate. (2 ) "NT" means "No test J. -34- This paper size applies to the Chinese National Standard (CNS) A4 specification (210X29 * 7mm) (Please read the notes on the back first and fill out this page). Order the central sample of the Ministry of Economic Affairs Printed by the Zhuhai Bureau Shellfish Consumer Cooperative A7 B7 V. Description of the invention (52) Example 28 8: Corn rootworm test The 3000 ppm biologically active stock solution (described above, related to Example 25) was diluted to 100 ppm For each of the 42 compounds reported in Table I, pipette 2.5 ml of the liquid sample into a 100 mm diameter selective fox disc with filter paper (What man 3) placed at the bottom. Two corn seedlings were soaked in l 〇ppm solution lasted for one hour, and then transferred it to culture m. After 24 hours, every Five second-instar corn rootworm larvae were added to the disc. Five days later, the surviving larvae were examined and the control% modified by the Albert's formula was calculated. The test results are shown in Table 11 below. F. Example 29: Test of Myzus persicae leaves A 3000 ppm biologically active stock solution (described above, related to Example 25) was diluted to 500 ppm 'and used to treat a farm infected with peach field insects. Test results Listed in the following Table II, “G p A ,, stopped. On the sixth day after treatment, the control% is estimated. Example 30: Pre-emergence herbicide test In addition, each of the 4 compounds listed in Table I was tested as Efficacy of herbicide before germination "In this test, a 3,000 ppm solution of each compound prepared as described in Example 25 was added to dilute with distilled water to 2 5 0ρρη. The test of each 42 compounds was based on the above 25 ppm solution. 46 ml part of the sample is 4.5 kg (10) pounds (11.2 kg / ha) per ------------ 55. This paper size applies to the national standard (CNS) Α4 Specifications (210 × 297 mm) (* Please read the note on the kidney face ^, fill in Buy) • J -, ----------- d ------ ΐτ- A7

Printed by Shellfish Consumer Cooperatives, Central Bureau of Standards, Ministry of Economic Affairs. Proportions are applied to the surface of the soil, which is contained in 11.25 cm (4 1/2 inch) plastic pots. In these pots, the following weed seeds are planted. -Domain shamrock, test results are listed in the "VL" column of Table 111 (below), _ mandala, test results are listed in "JW," of Table 111 (below), stop. _ 圆 叶 奉 牛 ' The test results are listed in the "TM" of Table 111 (below), and the test results are listed in the "SG" column of Table 111 (below). -The test results of "Zongzi" are shown in Table Z! (Below) ), "BG," stop; and • Bothwort, test results are shown in Table m (below), "Gf," stop. Determination of the control two weeks after treatment, compared with the untreated control group, the control% of each of our weeds was determined. The test results summarized in Table III show that the compounds of the present invention have good · to-excellent Weeding function. The size of this paper applies to China National Standard (CNS) Α4 specification (210 × 297 mm), language (please read the notes on the front side and fill in this note)

B V. Description of Invention (M) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs III Compound No. JW TM VL BG GF SG 1 0 0 0 0 0 15 2 20 40 65 20 20 20 3 100 100 100 100 100 100 4 100 100 100 100 100 100 5 20 20 15 0 70 70 6 100 50 100 100 100 100 7 0 0 0 0 0 8 10 0 0 0 0 10 9 100 50 100 85 100 100 10 60 25 95 40 100 80 11 90 50 100 95 100 95 12 0 0 ^ 0 0 0 0 13 100 '50 70 60 40 95 14 100 40 100 100 100 100 15 100 80 100 100 100 100 16 0 0 0 0 0 0 17 0 0 0 0 0 0 18 0 0 0 0 10 0 19 0 0 0 0 0 0 0 (Read the notes on the back " .f to fill out this page) -37- This paper size applies to China National Standard (CNS) A4 (210X297 mm) V. Description of the invention (55) Consumer cooperation of the Central Bureau of Standards of the Ministry of Economy Du printed tabulation III Compound number JW TM VL BG GF SG 20 0 0 0 0 0 0 21 20 100 40 0 20 20 22 0 0 20 0 0 23 0 15 0 0 0 15 24 0 0 0 0 0 0 25 0 100 0 30 0 30 26 15 95 30 90 30 20 27 0 0 0 0 0 28 0 30 0 0 0 0 29 0 0 0 0 0 0 30 0 0 0 40 25 0 31 30. 0 '30 15 0 0 32 0 80 i 20 15 0 0 33 20 20 0 30 0 40 34 0 0 0 0 0 0 35 35 0 0 20 0 0 36 40 100 80 75 60 0 37 0 0 0 0 0 38 0 95 15 30 50 50 —38—

(Read the notes on the back first and fill in this page)

This paper size applies to Chinese national standards (CNS > A4 size (210X 297mm) A7 B7 V. Description of invention (% Table III Compound No. JW TM VL BG --- GF --- ^ SG 39 0 70 30 0 0 ------- 0 40 Q 20 0 0 1.. _ 0 ----- 90 41 0 0 0 ------ 0 ----- 0 42 0 15 50 0 20 30,- I ":-^^ 1 n. II--^ 1) -./^-^ j I (¾ Read the notes on the back 3 and fill out this page) Example 3 1: Post-emergence herbicide test Each of the 42 compounds of the invention was used as a weed killer after germination, and a 3000 ppm stock solution (prepared according to the steps described in Example 25) was applied to the leaves of each of the weeds listed in Example 30. The above solution was used to mix them with each other. The leaves of the weeds are moistened to the tip of the dripping leaves. This solution is applied to the leaves by atomizing the mouth with a "DeVilbiss" (trade name) sprayer. The spraying of the weed leaves is performed six days after the leaves germinate After treatment with the compound of the present invention for two weeks, compared with the untreated control group, weed control% was determined, and the test results were summarized in the following table jv. • 39- This paper size Applicable to China National Standard (CNS) A4 specification (210X297 public directors)-Ordered by the Ministry of Economic Affairs, Central Bureau of Standards, Printed by the Consumer Cooperatives 386019 V. Description of the invention (57> A7 B7 Printed by the Consumers' Cooperatives of the Central Standards Bureau of the Ministry of Economics IV Compound No. JW ΤVL VL BG GF SG 1 95 100 60 60 35 50 2 100 85 75 90 75 100 3 100 100 100 100 100 100 100 4 100 100 100 100 100 5 100 100 95 95 85 100 6 100 100 98 100 100 100 7 100 100 30 70 60 80 8 80 15 25 15 10 100 9 100 40 70 50 75 100 10 100 90 95 50 75 100 11 100 100 90 35 85 95 12 80 90 80 50 80 50 13 100 • 95, 100 75 100 80 14 100 100 100 100 100 100 15 100 100 100 100 100 100 16 70 100 80 80 50 50 17 95 100 100 90 60 80 18 100 99 95 30 60 20 19 100 100 100 90 100 100 Please read first Please pay attention to this page before filling in—40— This paper is in accordance with Chinese National Standard (CNS) A4 specification (210 × 297 mm) Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs mmu a7 B7 V. Description of the invention (38) Table IV Compounds JW TM VL BG GF SG 20 50 90 90 50 50 80 21 90 100 100 80 100 95 22 100 100 95 80 100 90 23 100 100 100 70 80 10 24 80 100 50 50 30 10 25 — 100 100 100 95 60 26 100 100 100 100 50 27 — 100 90 80 50 60 28 — 100 90 90 100 60 29 — 100 95 95 100 100 30 — 100 95 30 90 50 31 — 85 100 40 50 0 32 — J00 ”00 60 40 20 33 — 100 100 70 30 10 34 — 100 95 40 15 0 35 — 100 80 80 30 20 36 — 100 100 100 50 100 37 — 100 95 80 30 50 38 — 100 90 95 30 25 (Before you pay attention to the wealth ..., fill out this page) Order This paper size applies Chinese National Standard (CNS) A4 (210X 297 mm) 386019 a? B7 V. Description of the invention (59) Table IV Compound No. JW TM VL BG GF SG 39 0 100 80 30 50 50 40 0 100 95 50 30 80 41 0 50 100 20 50 20 42 10 30 20 30 20 30 ------- ^ --- T ... 4 clothes-, ν C (¾Read the 15 ^ notice first 'Hou refill this page) Summarizing the above data, we found that all the compounds listed in Table I (above)-except for the compounds numbered 12, 20, 41, and 42-could be effective herbicides; They also found that number 1,2,5,6,17,19,20, and 40. 22,23,25,31-33,37 compounds can be used as an effective insecticide. μ Disclosed herein is a novel, arylpyrimidine group that can be used as both a herbicide and a pesticide. Although our invention is described in detail with reference to some preferred embodiments, we need to understand that our preferred embodiments cannot be used to limit the scope of our invention, and we want to state all the scope of this invention in the following. Fan Guzhong in applying for a patent. -42- This paper size applies Chinese National Standard (CNS) A4 specification (210X297mm).

Claims (1)

No. 84107123 Patent Application Chinese Patent Application Revision 1 ^ Bian 88 Beiyueyue 6, Applying for Patent Fan Yuan Supplement 386019 1 · A compound with insecticidal activity, which has the following structural formula I, la Or lb, among which: the Ministry of Economic Affairs's sample rate, and shellfish consumer cooperation, Du Yin oxygen R1 is hydrogen or CrC6 alkyl; R2 and R6 are independently hydrogen or Cl-C4 alkyl; R3 is hydrogen or alkyl; R4 is Gas or cvc4 alkyl; r5 is stupid methyl, 2-tetrahydrofurylmethyl, optionally selected from (^-(^ alkoxyquinyl, linear, branched or cyclic Cl-c6 alkyl or c2- c6 alkenyl; Ci C6 oxyhalo, halo 1, halo or Re · C〇2-R7 group, where ^ is (: 丨 _c3 alkenyl or Cl_c3 @ alkenyl and R7 is c丨 -c6 alkyl, and X and Y are independently sulfur or oxygen. 2. According to the compound of the patent application, item J, in which R1 is argon or Ci_ & Zhang ΛΑ 逋, the rate of use is CNS A4 ^ (210x297) --- -C— (Please read the ^^ back and the above notes before filling in this 1-Order No. 84107123 Patent Application Chinese Patent Application Scope Revision 1 ^ Bian 88 for the month 6th, apply for a patent garden supplement £ 386019 1 · A compound with insecticidal activity, which has the following structural formula I, la or lb, where: The Ministry of Economic Affairs has a sample rate of 扃 shellfish consumer cooperation Du Yin oxygen R1 is hydrogen or CrC6 alkyl; R2 And R6 is independently hydrogen or Cl-C4 alkyl group; R3 is hydrogen or alkyl group; R4 is gas or cvc4 alkyl group; r5 is benzyl methyl group, 2-tetrahydrofurylmethyl group, and the selectivity is (^-(^ Alkoxyalkyl, straight-chain, branched-chain or cyclic Cl-c6 alkyl or c2-c6 alkenyl; Ci C6 oxyoxy fumaryl, halo 1-based, halo-based or Re · C〇2-R7 Where ^ is (: 丨 _c3 alkenyl or Cl_c3 @ alkenyl and R7 is c 丨 -c6 alkyl, and X and Y are independently sulfur or oxygen. 2. Compound according to item J of the patent application , Where Rl is argon or Ci_ & Zhang ΛΑ 逋 uses a medium rate (CNS) A4 ^ (210x297) --- -C— (Please read the ^^ back, the notes above, and then fill out this one.-Order A8 B8 C8 D8 886019, patent application C3 Tiger base; R2 is argon; R3 is argon, or C ^ -C ^ alkane R4 is argon; R5 is 〇1 to (: 4 alkyl; R6 is argon; and X and γ are both oxygen. 3. The compound according to item 1 of the patent application, wherein Ri is methyl; R2 is Argon; R3 is methyl; R4 is argon; R5 is methyl, ethyl, isopropyl or tertiary-butyl isopropyl; R6 is argon; and X and γ are both oxygen. 4. One control includes wind Compositions of lice and aphid insects, which contain (A) an effective dose of a compound in the patent application area item i; and (B) an appropriate carrier for them. 5. According to the patent application group item 4 A composition containing (A) an effective amount of a compound according to item 2 of the patent application scope; and (B) an appropriate carrier for them β 6. a composition according to item 4 of the patent application scope , Which contains ... (A) an effective amount of a compound according to item 3 of the scope of patent application; and (B) an appropriate carrier for them. Ministry of Economic Affairs, Central Sample Rate Bureau, Shellfish Consumer Cooperative, India 7. — — Species A method for producing insects including wind lice and aphids, which comprises applying an effective amount of a composition according to item 4 of the scope of patent application to a place so as to control the insects located there. 8. According to item 7 of the scope of patent application A method comprising applying an effective amount of a composition according to item 5 of the scope of patent application to the premises "9. A method according to item 7 of the patent scope of patent application, which includes applying a substantial amount according to item 6 of the scope of patent application The composition is applied to the premises β 2- This paper ft scale is applicable to China National Standards (CNS) A4 specifications (2 丨 0) < 297 public directors)