JPH05500063A - Herbicide oxabicycloethers - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

[Detailed description of the invention] name Herbicide oxabicycloethers References to related applications This application is filed on September 11, 1989, currently pending U.S. Application No. 0 This is a continuation-in-part application of 7/431,734.

field of invention The present invention provides novel oxabicycloether derivative compounds and derivative compounds thereof. and their use in regulating undesirable plant growth. The invention relates to methods of using the compounds or compositions of the invention. More particularly, the invention has broad It is herbicidally active against weed species in the surrounding area and is effective against rice, grain and broadleaf crops. It relates to various compounds, compositions, and their uses that have been shown to be safe.

Background of the invention Payne et al., U.S. Pat. No. 4.567.283 and Payne et al., U.S. Pat. No. 4,670,041 discloses herbicidal bicyclic ethers of various formulas. Ru.

Both U.S. Patents 4.798,621 and W2B, 902.219 Discloses fertilisers and their use in breeding cattle.

U.S. Patent 4.486.219 describes the formula: discloses bicyclic ethers.

One object of the present invention is to provide herbicides that exhibit herbicidal activity against a variety of economically important weed species. It is an object of the present invention to provide compounds and compositions that can be used. Another object of the present invention is to and to provide herbicidally safe compounds and compositions for broadleaf and broadleaf crops. Ru. A feature of the present invention is novel oxabicycloethers exhibiting useful herbicidal activity. The purpose is to supply These and other objects, features and advantages of the invention are described below. The invention which is clear with respect to the description is: I II I [I TV V VI X and Y are independently H or l;tc(R'XR')OR"t', and Z is C( R'')(R')OR1, where R1 is H or linear C, -C, alkyl. , R2 is H, C, -C, 7/l/kill, C, -C4 Fluke, :, le, Cx C 4 fulquinil, 7 ale, ttaL! Ph, 0HSCNSOR', 5O2R-Ph C, -C4 alkyl substituted by SO2, R8, Co, R" or CO, H and R3, R4, R9 and R1° are independent rH, Ct C4 full + full, C2C4 full Le’f-JLt, quinyl at C2C47, or OCH5 or OCH,CH3 CI C, alkyl substituted by, and R' is C, -C, 7VL4, C I C47 'r-nyl, c, C47/lz-kyl, benzyl, or OR8, O C, -C, alkyl substituted with CF, R8 is C, -C, alkyl, Q is WCH2 or Wit arbitrary 1: F, CI, Br, C, -C37/l/kill, Cr C37/l/ Koxy, OH, CN5C, -c, ha0furkyl, CI-c3 haloalkoxy, C , -c, alkylthio, C2-c4 alkenyl and C2C4 alkynyl phenyl optionally substituted with 1-3 selected substituents, or W is a ring in which each ring is arbitrarily selected from F, CI, Br, CH3 and OCHs. 0-2 nitrogen, 0-2 oxygen or or a 5- or 6-membered heterocyclic ring containing 0-2 sulfurs, Zl is CH2, NR,, ols or forms a double bond with adjacent carbons can, R, is H or C, -C3 alkyl, R' is H, halogen: z, Ra, OR "SSR"*1tCNTat), R' is HSF%CI, CH3, OCH3, O H or OR8, ql is 0.1 or 2, and q is 0, 1 or 2, However, as a condition, 1) A small number of X and Y (both are 1(Ili:IC(R3XR')OR5, 2) R3, R4, R9 and RIG each contain 4 or less carbon atoms; Ori, 3) In formula II, if R1 is H, then X is likely C(R3XR')OR' and Y is H, 4) the sum of q and ql is 0, 1 or 2, and 5) the sum of Q and ql If the total is 0, then Zl is CH, Compounds of the formula selected from the group consisting of and their stereoisomers.

Representative examples of the above heterocycles include, but are not limited to, the following: Not: virol, furan, thiophene, tetrahydropyran, tetrahydro Furan, inxazole, oxazole, pyrazole, imidazole, thiazole pyridine and pyrazines.

Compounds of the invention that are suitable for their biological activity or ease of synthesis are: 1. 1-2 W arbitrarily selected from F, CI, Br, CH3 and OCH3 is phenyl optionally substituted with a substituent, or W is each 1-2 rings optionally selected from FlCl, I3r, CH3 and OCH3 Tetrahydropyran, tetrahydrofuran, which may be substituted with a substituent, thiophene, isoxazole, pyridine or pyrazine; Q is Q-10-2C) 3 >4 g-5o-a Aggression “　’=9-9 9-ffOQ-11Q-12 and R1 is H or C,-C3 alkyl, and R5 is other than benzyl, Formula ■, II, III, dv, v, v’r, vn, or VrII (7) compound, 2, R2 is HSC+ C37/lzki/Iz, Cz-Cs7 is or C2-Cs furquinyl, A compound according to preferred item 1.

3, R3 is HSC, -C37/l/kill, C, -C, full '7 = #matahaCz -Cs is fluquinyl, R' is H, C, -C, 7/l/kyl, C2-Cs alkenyl or C2-c, a Luquinyl, R5 is H, c, -c, alkyl, C, -C, alkenyl or C, -C, alkyl Nil, R9 is H, Cl-C37/l/kill, Cs C4 full month-At also l; IC3C 47 is quinyl, R'0 is H, C, -C, furkyl, C3-C4 alkenyl, Cs C47k is quinyl, Compound according to preferred item 2.

4. Q is Q-1, Q-3, Q-6, Q-7 or Q-15, 12. Compound A compound according to preference 4, wherein is of formula VIII.

Particularly preferred because of its biological activity and ease of synthesis are 2-(]- ] Ethyl-1-methoxypropyl-6-(phenylmethoxy)nia-oxabisi Preferred item 5 is chloro[2,2,1]hebutane, (2-exo, 6-exo). Compounds listed above and 2-(ethoxymethyl)-5-methyl-4-(phenylmethoxymethyl) c)-6-oxabicyclo[3,2,1]octane.

(2-endo, 4-endo) The compound according to preferred item 7.

All are preferably virol, furan, thiophene, tetrahydrobilane, tetra Hydrofuran, Isoxazole, Oxazole, Pyrazoleimidazole, Tri Can be selected from the group consisting of azoles, pyridines, and pyrazines.

Compounds of formula i-VIII with WCH20 groups syn for oxygen-containing bridges The herbicide is generally more active than the anti-form. The invention arises from the synthesis and all herbicidally active forms resulting from carefully prepared mixtures. There is.

Compounds of the present invention are suitable substituted oxabicycloalkanols (Ia-VI IIa) with the formula WCH,X (where X is a halogen atom or mesyloxy, It is produced by processing with a compound such as a hydroxyl group. child As shown in reaction formula 1, the reaction is performed using a strong base such as alkali metal hydride. For example, ethers, aromatic hydrocarbons, dimethylformamide, etc. It is carried out in an inert solvent such as. A suitable reaction temperature is preferably between 20°C and 100°C. be. The product ethers are recovered and isolated by conventional techniques.

Also within the scope of the invention are compositions suitable for regulating undesirable plant growth. be included. Such compositions include an effective amount of any of the compounds disclosed herein. and at least one surfactant, solid or liquid diluent.

Methods for regulating undesirable plant growth are also encompassed within the scope of this invention. It will be done. These methods are disclosed herein in effective amounts to the location sought to be protected. It consists of applying any of the compounds.

Of particular importance is the manner in which the rice is located in the area to be protected.

The alkylating agent WCH2X can be added to the alcohol by conventional methods known to those skilled in the art. Produced from similar WCH,OH.

Alcohols WCH20H are commonly known in the art and are most conveniently Phenylalkylcarboxylic acids, phenoxyalkylcarboxylic acids, phenylthio Alkylcarboxylic acids, benzyloxyalkylcarboxylic acids, and benzyl can be derived by Friedel-Krach type cyclization of derivatives of thioalkylcarboxylic acids. metal hydrides of the corresponding bicyclic ketones (e.g. sodium borohydride) Produced by reduction.

For details, please refer to a) T., Laird, Comprehensive Organi. CollIprehensive Organic Ch emistry), D, Barton (Ba, rton) $ and W, D, Oris (0], H, 5)lii collection, part 1! , 1:1.65-1768, Burgamon Pu. Les, New York (1979), b) M, H.

Par 7 - (Palmer) and Scollick, The Journal of the Chemical-7Yety CD, Chem, Sac, , C,), (1968), 2833, c) C, E, Dalgliesh (Dal Gliesch) and Mann, The Journal of the Chemistry Cal Society (J, Chew, Soc,), (1945), 893 , d) C, D, llurd and S Hayao, the Journal of the American Chemical Society (J, Arm, Chew, Soc, ), (1954), 76.4299 and 5056, and e) R, Lesser, A, Mitsu, while the standard William The reaction described in Equation 2 is used when son ether synthesis proves to be problematic. Compounds of formula 1-4III can also be prepared by the coupling steps described above. can. This process uses Lewis acidic metal oxides, where the metal is insoluble. Halide ions can be removed by forming a precipitate. for example, Silver(I) oxide can be used, with silver halide being the co-product.

Other metal oxides that can be used are HgO, Cab, MgO. N,N-dimethy -formamide and ethereal solvents such as diethyl ether, tetrahydride Lofuran, dioxane, or 1,2-dimethoxy-ethane are suitable solvents. . Other solvents that give similarly good yields include dipolar aprotic solvents, e.g. Dimethyl sulfoxide, acetone and N9N'-dimethylpropylene urea are Included.

n is 1 or 2 Oxabicycloalkanols (Ia-VIIIa) are generally one or more It can be obtained by the following steps: directly a) by simply converting the epoxy alcohol intermediate product; Epoxidation of unsaturated cyclic alcohols with or without isolation - by cyclization , indirectly b) by the Diels-Alder reaction between furans and genophiles. or C) by Diels-Alder reaction between other dienes and genophiles. process.

Non-limiting illustrations of the preparation of representative compounds are provided below.

Compounds of formula Ia are synthesized according to the sequence shown in Scheme 2. Deals Alder adducts are prepared from readily available furans as well as from genophiles, e.g. Manufactured from acrylate esters, acrolein, acryloyl chloride, etc. (Murai et al., The Journal O et al., Preteen of the Chemistry Cal Society of Japan (Bull, Chem, Soc, JP) n, ), 5e, 3339 (1984), and the Diels-Alda method. Regarding the theory, Laszlo et al., Tetrahedron Letters (Tet , Let, ), Lambda, 4387 (1984)). For example, Eels-Alder adduct (2) is made from furan (3) and acryloyl chloride. will be built. (2) with alcohol and base at 0° C. to ambient temperature, Prepare the corresponding ester. This intermediate product is expressed as shown in reaction formula 3b. and a suitable Grignard reagent or reducing agent (e.g. lithium aluminum hydride). ).

Optionally, inactivate using an alkyl halide or sulfonate and a base. in a neutral solvent such as tetrahydrofuran or N,N-dimethylformamide. Processing at ambient temperature to 150<0>C produces (4). Alcohol (4a) or ether (4b) such as hydrogen peroxide or m-chloroperbenzoic acid. Oxidation with peroxide in a suitable solvent such as methylene chloride produces epoxy generated by the code. As shown in reaction formula 3C, Krishnamurthy (Kr ishnamurthy) et al., The Journal of the American Chem. Le Society (J, ^mer, Chem, Soc, ), 95.84 86 (1973), for example by triethyl hydrogenation. treated with a reducing agent such as lithium boron or lithium aluminum hydride. Alcohol Ia is produced by reductive ring opening of the epoxide.

On the other hand, compounds of formula Ia can also be synthesized according to the sequence shown in Scheme 4. , in which the groups R3 and R4 can vary independently.

Diels-Alda made from furan (3) and vinylcarbonyl (6) - Treat the adduct (5) with a suitable Grignard reagent or reducing agent to 7) Manufacture. Alcohol Ia can then be prepared as already described in Schemes 3b and 3c. It can be manufactured by the process described above or a modification thereof.

(i) (6) (5) Compounds of formula Ia, especially where R3 and/or R4 are allylic or vinylic can be produced according to the sequence shown in Reaction Scheme 5. Reaction formula 3C Treating the Diels-Alder adduct (8) with peroxide as described in do. This intermediate product is treated with a suitable Grignard reagent, such as magnesium halide. alcohol (9) by treatment with muvinyl or allyl magnesium halide. Manufacture. Alcohol Ia can be obtained by the process already described in Reaction Schemes 3b and 3C. or modified methods thereof.

Compounds of formula Ia can also be synthesized according to the sequence shown in Scheme 6, or by the sequence shown in Scheme 6. Journal of the American Chemical Society (J, Amer, Using the method of Chew, Soc, ), Edan, 1161 (1948), Diels-Alder adduct (10) is a mixture of furan (3) and dicarbonylgeno filtrate, such as maleic anhydride. Alcohol Ia has reaction formula 4b and steps already described in 4c or 5b and 5c or those It can be produced by a modified method.

()) YmQl, f (to) Compounds of formula IIa can be prepared using the steps already described in Scheme 7 or variations thereof. It can be manufactured by Cyclohexene (11) is Alder ) Other methods, Hemische "Berichte" (Chem, Ber, ), 8 F>-1 1312 (1953) by Diels-Alder reaction. can. Diol derivatives are obtained by treating diesters with Grignard reagents or reducing agents. Manufacture. Monoalkylation using the method described above yields a mixture of ethers ( 12) is generated. As taught in U.S. Patent Application No. 4,542,244 and treatment of (12) with peroxide and acid to produce alcohol IIa.

In situations where the endo form is desired, it is 2-exo-IIa to the corresponding ketone. oxidation and subsequent ketolysis using a reducing agent such as sodium borohydride. Obtained by reduction of

[11) Compounds of formula IIIa can be used in any of the steps already described in Scheme 8 or in any one of them. It can be produced by a modified method. Cyclohexene (13) i1 feeder ( Fieser) Other Methods, The Journal of the American + J Kan Chemical -Society C1, ^Ioer, Che-j2), 64, 802 (19 Genophile, which can be easily obtained by Diels-Alder reaction using 42) such as maleic anhydride, and diene components such as isoprene or butadiene. It can be manufactured from (13) with Grignard reagent or reducing agent Processing to produce diol derivatives. When monoalkylated using the method described above, , ether (14) is produced.

(14) as taught in U.S. Patent Application No. 4.542,244. Treatment with oxide and acid produces alcohol IIIa.

In situations where the endo form is desired, it converts from 2-exo-IIIa to the corresponding keto using a reducing agent such as sodium borohydride. Obtained by reduction of ketones.

1 country (ff3) (ts xxa Compounds of formula IIIa can be prepared using the steps already described in Scheme 9 or their It can be produced by a modified method. Cyclohexene (15) is Diels-Al diene (16) and readily available genophiles, e.g. Water can be produced from maleic acid.

(15) is treated with a Grignard reagent or a reducing agent to produce a diol derivative . Monoalkylation using the method described above produces ether (17). Before IIIa is prepared by treating (17) with peroxide and acid as described above.

In situations where the endo form is desired, it converts from 2-exo-IIIa to the corresponding keto using a reducing agent such as sodium borohydride. Obtained by reduction of ketones.

Compounds of formula IV can be prepared by the method described in Scheme 10. 1,5-cyclohydrochloride using trimethylamine oxide as a stoichiometric oxidant and a stoichiometric oxidant. Hydroxylation of looctadiene followed by a suitable alkylating agent as described above. Williamson ether coupling reaction using WCH2X produces ether (18) is generated. Oxidation of this alcohol using Heap reagent The ketone (19) is formed using an amide base under conditions known in the art. alkylation with a suitably substituted ketone. Dissolve the resulting alcohol as described above. When treated with an alkyl halide in the presence of a strong base, (20) is produced. Ru. Add a suitable Grignard reagent or reducing agent (e.g. sodium borohydride) When added to the carbonyl group, alcohol (21) is generated, which is cyclized to form the alcohol Oxysilvering/desilvering process [Bordwell, The Jatil] Manufacture.

(1@) (1g) Va Compounds of formula YIIa (X=H) and VIa are those described in Reaction Scheme 11 It can be manufactured by the method. Diesters (22-) and (23) are examples Ruden et al. (The Journal of the American Chemical ・Society 0. ^mer, Chet Soc, ), DanJ16892 ( diene components readily available by the Diels-Alder method such as (1975); With isoprene or butadiene and dialkyl ketomalonates, for example can be manufactured. The esters are treated with Grignard reagent or is treated with a reducing agent to produce diols (24) and (25). The above method monoalkylation using Alcohols VIIa and VIa are produced. In situations where an end shape is desired , it converts 2-exo-VIIa or exo-VIa to the corresponding ketone. oxidation and subsequent ketone using a reducing agent such as sodium borohydride obtained by reduction of

(2li (25) nXa　’Inn Compounds of formula VIIa (Y=H) and Va can be prepared by the method described in Scheme 12. It can be manufactured by Diene (26) is obtained from the corresponding diene ester, For example, Corey et al. (Tet, Let) Grignard, as described by J. T., ), 30.2537 (1975). by addition of a reagent or reducing agent and subsequent alkylation of the alcohol formed. and can be manufactured. Jurczak et al., The Journa Le of the Organic Chemistry (J.

The Diels-Alder reaction between (26) and glyoxylate yields (27) and and (28) are generated. (27) and (28) with Grignard reagent or reduction treatment with a chemical agent to produce alcohols (29) and (30). As above When treated with peroxide and acid, alcohols VIIa and VIa are formed. do. The endo alcohol is obtained as described in Scheme 11.

(26) (29) (go) Compounds of formula VIII can be prepared by the method described in Scheme 13. Wear. Compound (4) was treated with trialkylamine N-oxide and catalytic tetroxide. Treatment with sumium produces triol (31).

Alkylation of (31) with QX (e.g. benzyl bromide) and subsequent R5 Treatment with X and a strong base produces VIII.

acid, 1,4-dimethyl-, methyl ester, (endo and exo, racemic ) Acryloyl chloride (32.8 ml, 0.40 mol) was added in an ice-water bath under nitrogen atmosphere. and cooled to 0°C. 0.5 aluminum chloride (1.60 g, 0.012 mol) g each was added with stirring. The mixture was stirred for 10 minutes at 5°C, then It was cooled to -65°C using a Ropanolu dry ice bath. 2,5-dimethylphenyl Run (38.4 g, 0.40 mol) at -65°C to -50°C for 1.5 hours. Added drop by drop. After the addition was complete, the mixture was stirred for 1 hour. Methyl chloride Lens (250ml) was added to the mixture. The mixture was then mixed with triethylamine (48, 4 g, 0.48 mol) and methanol (60 ml). The mixture was cannulated over 10 minutes at -55°C to -40°C. mixture The mixture was stirred at -65°C for 1.25 hours and then allowed to warm to ambient temperature. I met. The mixture was poured into 500ml of water. Separate the phases and dilute the aqueous layer with methane chloride. Extracted twice with Len. - Combine the combined organic layers in saturated sodium bicarbonate and brine. Wash with solution, dry over magnesium sulfate and concentrate in vacuo to give 35 ．． 12g of yellow oil remained. 3=1 hexanes on 800 g of silica gel: By flash chromatography in ether, 17.34 g of the endoisomer and 11.82 g of the exo isomer were produced.

NMR (CDCIs) endoisomer: 6.22 (d, IH), 6.03 (d.

IH), 3.61 (s, 3H), 2.88 (dd, LH), 1.91 (ddd, IH), 1.80 (ddd, IH), 1.70 (s, 3H), 1.56 (2,3 H).

NMR (CD Cl g) Exo isomer: 6.18 (d, IH), 6.1 2 (d.

IH), 3.69 (s, 3H), 2.52 (dd, IH), 2.0 (d d, IH), 1.66 (dd, IH), 1.62 (s, 3H), 1.50 (2, 3H).

MB: 7-oxabicyclo[2,2,11 hepte-5-c2-methanol , 1,4-dimethyl-,exo-1 (racemic) lithium aluminum hydride (2.3 g, 60.0 mmol) in 100 ml of dry tetrahydride under nitrogen atmosphere. Added to Lochran. The mixture was heated to reflux for 15 minutes, then cooled to 0°C. . 7-Oxabicyclo[2,2,1]hept-5-cy-2-carboxylic acid, 1,4 -dimethyl-, methyl ester, (exo, racemate) (14.3g, 78.6 (mmol) in 100 ml of tetrahydrofuran dropwise over 1.5 hours. Added. The mixture was then allowed to warm to ambient temperature and for an additional 4.0 hours. and stirred. The mixture was cooled to 5°C in an ice-water bath, 2.3 ml of water, 2.3 m 1 of 10% sodium hydroxide and 2.3 ml of water were added. Suction filtration of solids and washed with 40 ml of cold tetrahydrofuran. filtrate Concentration in vacuo produced 9.5 g of colorless oil.

NMR (CDCIs): 6.22 (d, IH), 6.12 (d, IH), 3.83 (m, IH), 3.74 (m, IH), 2.17 (dd, IH ), 1.86 (m, IH), 1.68 (dd, IH), 1.59 (s, 3H) , 1.58 (s, 3H), 1.51 (dd, IH).

IR (CH2C1□): 3620.3480.1385.1330.1190. 1140.1120.1075.1035.975.365cm”.

MS (CI): 155 (M+1), 137.109.107.96.95. 93° Step C nia-oxabicyclo[2,2,11 hepten-5-ene, 1,4-dimethyl -2-[(phenylmethoxy)methyl]-1 (exo-, racemic) sodium hydride (1.54 g, 3.85 mmol 60% oil dispersion) was washed with hexanes. , decanted and suspended in 20 ml of dimethylformamide. 4.7 5 g (30,8 mmol) of 7-oxabicyclo[2,2,1]hepte-5- C2-methanol, 1,4-dimethyl-.

A solution of exo (racemate) in 40 ml of dimethylformamide at 20°C. Added dropwise over 45 minutes. The mixture was stirred for 45 minutes at ambient temperature.

Benzyl bromide (6.05 g, 35.4 mmol) was dissolved in 30 ml of dimethylforma. Add dropwise into the medium over 30 minutes. Stir the mixture for 20 hours at ambient temperature. Stirred. The mixture was poured into 350 ml of water and extracted three times with methylene chloride. . - Wash the combined extracts with saline, dry over magnesium sulfate, and Concentration in air gave 7.83 g of a yellow oil. on 400g silica gel By flash chromatography in 3:1 hexanes:ether of 3. 77 g of pale yellow oil was produced.

NMR (CDCI: 7.40 7.26 (m, 5H), 6.12 (s, 2 H), 4.51 (dq, 2H), 3.60 (dd, IH), 3.43 (d d, IH), 1.97 (m, LH), 1.70 (dd, IH), 1.56 (s , 3H), 1.53 (s, 3H), 1.18 (dd, IH),.

IR(CH2CI2): 1595.1450.1380.1360.1330. 1195.1140.1120.1090.1035.1025.860° Analysis Calculated value for Cl682°02: C, 78, 69; H, 8, 20 actual measurement Value: C, 78,80; H, 8,37° Stage D: 3,8-dioxatricyclo[3 ,2,1,0sup2.5up4Co-octane,1,5-dimethyl-6-[(Fe Nylmethoxy)methyl]-1 (exo, racemic form-) 3.60 g (15.0 mmol) of 7-oxabicyclo[2,2,1cohep Te-5-ene, 1,4-dimethyl-2-[(phenylmethoxy)methyl]-(ex 3.56 g (16,5 mmol) of 80% technical grade m-chloroperbenzoic acid was added at 0°C to 10°C. . The mixture was stirred at 0°C to 10°C for 1 hour and then at ambient temperature. surroundings After 20 hours at temperature, the mixture was cooled to 0° Oo for 5 hours and filtered. , and washed with cold methylene chloride. The filtrate was saturated with 10% sodium sulfite. Wash with sodium bicarbonate and brine, dry over magnesium sulfate, and and concentrated in vacuo to give 4.05 g of pale yellow oil. 150g silica By flash chromatography in 1:1 hexaneconytyl on gel , 3.30 g of colorless liquid was produced.

NMR (CDCIg): 7.40 7.26 (m, 5H), 4.48 (dq .

2H), 3.52 (d d, IH), 3.26 (dd, IH), 3.1.7 ( d q, 2H), 2.10-1.98 (m, IH), 1.85 (d d, I H), 1.47 (s, 3H), 1, 46 (s, 3H), 1.18 (d d, IH).

IR(CH2CI2):1451.1400.1380.1362.1308. 1218.1192.1120.1090.1025.968.915.880 ．． 870.830.810Cm-'.

MS (CI): 26gM+1), 183.181.169.153.139 ．． 91° Step E: mixed with -5-[(phenylmethoxy)methyl] regioisomer 7-oxabicyclo[2,2,1]hebutanol-2--, 1,4-dimethyl -6-[(phenylmethoxy)methyl]-1 (exo, racemic) triethyl water Stirred IM solution of lithium borohydride (25.4 ml) in tetrahydrofuran 3.30 g (12.7 mmol) of 3.3 g (12.7 mmol) in 10 ml of tetrahydrofuran. 8-dioxatricyclo[3,2,1,0s up2,5up4]octane, 1 ,5-dimethyl-6-[(phenylmethoxy)methyl]-1 (exo, racemic ) was added at ambient temperature. After 3 hours under reflux, the mixture was cooled to 0°C. and 10.2 g of 10% sodium hydroxide solution were added dropwise. mixture Warm to ambient temperature and add 8.64 g of 30% hydrogen peroxide (76,2 mmol) was added dropwise.

The mixture was stirred at 40° C. for 30 minutes and then saturated with potassium carbonate crystals.

The mixture was poured into 100ml of ether and the organic layer was separated. aqueous layer Extracted with tel 3 times. - Wash the combined organic layers with brine and place on magnesium sulfate. and concentrated in vacuo to yield 4.45 g of a pale yellow oil. 15 Flash chromatography in 3:1 ether:hexanes on 0 g silica gel According to Raffy, 5-(phenylmethoxymethyl) isomer = 6-(phenylmethoxymethyl) 2.04 g of colorless oil was produced containing a 2:1 mixture of xy) isomers. .

NMR (CDCl s): 7.32 (m, 5H), 4.48 (m, 2H) , 3.77 (m, IH), 3.54 (m, IH), 3.20 (m, IH), 2 ．． 20 (m, IH), 1.90 (m, IH), 1.75 (m, IH), 1. 66 (m, ll-1), 1.45.1.43.1.41 and 1.38 (s , 6H, total), 1.30 (m, IH), 1, 12 (m, LH).

TR (CH2C1g): 3580.3460 (wide), 1452.1380 ．． 1363.1203.1090.1070.1027, so, racemic) and 2: 7-oxabicyclo[2,2゜1cohbutane, 1,4-dimethyl Thyl-2-(phenylmethoxy)-6-[(phenylmethoxy)methyl]-isomer body Sodium hydride (0.39 g, 9.73 mmol) was washed with hexanes and decanted. It was decanted and suspended in 10 ml of dimethylacetamide. In the suspension, 2 -5-[(phenylmethoxy)methyl colezi in 0 ml dimethylacetamide 7-oxabicyclo[2,2,1]hebutano-2-- mixed with the isomer 1,4-dimethyl-6-[(phenylmethoxy)methyl]-(exo, lace The mixture was added over a period of 20 minutes at ambient temperature. The mixture was heated at 65°C for 2 Stir for an hour and then add 1.66 g (9,73 Benzyl bromide (mmol) was added at 0°C. The mixture was allowed to warm to ambient temperature.

After 20 hours, the mixture was added to 100 ml of methylene chloride and 100 ml of water. I got it.

The phases were separated and the aqueous layer was extracted three times with methylene chloride. - Eating the combined organic layer Washed with brine, dried and concentrated in vacuo to yield 4.00 g of pale yellow oil. accomplished. 2=1 hexanes on 150g silica gel: flash in ether 1,90 containing a two-in-one mixture of isomers by microchromatography 7g of pale yellow oil formed.

NMR (CDCJ g): 7.32 (m, 10H), 4.58-4.36 (m.

4H), 3.54 (m, 2H), 3.20 (m, IH), 2.02 (m, I H), 1.88 (m, IH), 1.8-1.6 (m, LH), 1.47.1 ．． 45 and 1.43 (s, 6H total), 1.2-1.05 (m, 2H).

IR (CHzCl): 1605.1587.1495.1452.13 85.1372.1360, 1333.12o3.1185.1085.101 3.860cm-10MS (cl): 353 (M+1), 335.261.2 46.245.244.215.181.155.137.119.91゜Execution Example 2 acid, methyl ester (exo and endo, racemate) 93.0g (1,3 7 mmol) of furan and 0.50 g (8.6 mmol) of propylene oxide 47.0 g (0.52 mmol) of acryloyl chloride to a mixture of I added it. The mixture was stirred in the dark under a nitrogen atmosphere for 3 days. Then mix The compound was dissolved in 45.0 ml (0,556 mol) of pyridine and 45.0 ml of meth. Added to a solution of Knoll in 100 ml of methylene chloride. After addition is complete, mix Warmed things to ambient temperature. After 1 hour, water was added to the mixture and the layers were separated.

The aqueous layer was extracted twice with methylene chloride. -Wash the combined organic layer with water and saline, and dried over magnesium sulfate and concentrated in vacuo to give a 2:1 ratio of 66.3 g of a dark oil containing the xo:endo isomer was produced. 320 20:1 hexanes on silica gel: 4.0 g flush in ethyl acetate The endo and exo isomers were separated by microchromatography.

NMR (CDC) End: 6.44 (d, IH), 6.21 (dd, L H), 5, 17 (d d, I H), 5.03 (dd, IH), 3.64 (s , 3H), 3, 10 (d d d, IH), 2.10 (d d d, IH) , 1.58 (dd, IH).

NMR (CDC) exo: 6.37 (dd, 2H), 5.10 (dd, 2 H), 3, '73 (s, 3H), 2.44 (d d, 2H), 2. ,t 8 (d t, IH), 1, 56 (d d, IH).

oxabicyclo[2,2,11 hepten-5-ene, 2-(1-ethyl -1-methoxypropyl), exo-(racemic) 20 in tetrahydrofuran m1 (40 mmol) of 2M ethylmagnesium bromide at 0°C. (19.5 mmol) of 7-oxabicycloU2.2.1]hept-5-cy 2-carboxylic acid, methyl ester (exo, racemate) was added. Reflux the mixture Warmed to temperature. After 8 hours, the mixture was cooled to 0 °C and 20 ml of water was added. Ta. The mixture was acidified to pH 3 using 10% hydrochloric acid and then extracted three times with ether. Ta.

- Combine the combined organic layers, wash with brine, dry over magnesium sulfate, It was then concentrated in vacuo to yield 2.3 g of a pale yellow oil.

This intermediate product was dissolved in 50 ml of tetrahydrofuran and 0.65 ml of g (45.1 mmol) of 60% sodium hydride in oil.

The solution was warmed to ambient temperature and stirred for 10 minutes. Iodomethane (1°3g, 40.0 mmol) was added and the mixture was refluxed. After 20 hours, the mixture was cooled and poured into 100 ml of water. Separate the layers and ether the aqueous layer. Extracted twice with The organic layers were combined, washed with brine, and dried over magnesium sulfate. Drying and concentration in vacuo yielded 1.69 g of a yellow oil. 621 Hexanes: 1.27 g by flash chromatography in ethyl acetate A pale yellow oil was formed.

NMR (CDC1g): 6.40 (dd, IH), 6.28 (dd, 1)I) , 4.95 (dd, 2H), 3.19 (s, 3H), 1.77 (d d, I H), 1, 60 (m, 4H), 1.47 (d d, LH), 1.33 (d d, 1) 1), 0, 9 (d q, 6H).

E2.2.1 Cohebutane, 2-(1-ethyl-1- methoxypropyl)-6-(phenylmethoxy)-9[exo-(2-alpha , 6-alpha)] Following steps similar to those described in steps E and F of Example 1, 1. ．． 27 g (6,48 mmol) of 7-oxabicyclo[2,2°1]heptane , 1.9 g of 2-(1-ethyl-1-methoxypropyl) (exo, racemate) When reacted with (6.6 mmol) of m-chloroperbenzoic acid, 0.75 g of yellow Oil was obtained. Next, 1.0 ml (10 mmol) of triethyl borohydride lithium Upon reaction with um, 0.9 g of pale yellow part was produced. treated with benzyl bromide, Subsequent flash chromatography yielded 0.20 g of colorless oil. did.

NMR (CDCIs): 7.33 (m, 5H), 4.55 (m, 4H), 3 ．． 64 (dd, IH), 3.16 (s, 3H), 1.85-1.31 (m, 9 H), 0.89 and 0.88 (t,,t,6H).

3-Dimethatol, (exo)- Furan (85.0 ml, 1.17 mol) was dissolved in anhydrous maley in 100 ml of ether. acid (81.0 g, 0.827 mol). After 20 hours, the precipitated solid was filtered off and washed with ether to give 104 g of a white crystalline solid.

34.0 g of Diels-Alder adduct was added to hydrogenated aluminum as described above. Reduction with umlithium produced 28.0 g of oil.

NMR spectra were taken from the literature [Das et al., The Journal of Medica Le Chemistry (J, Med, Chem), Dan 1.930 (1988 )] was the same as that reported in .

NMR (CDCI 3) + 6.40 (s, 2H), 4.70 (s, 2H) ), 4.00 (wide, 2H), 3.80 (m, 4H), 1.95 (m, 2H) .

IIR only B nia-oxabicyclo[2,2,11 hebutane, 2,3-bis(etho) ximethoxy)-5-hydroxy-1[2exo-(2 alpha, 3 alpha, 5 Alpha)] 14. Using ethyl iodide and sodium hydride. , Og (0,0897 mo cis-7-oxabicyclo[2,2,1]hepten-5-ene-2゜3-dime Alkylation of Tatour was carried out as above to give 15.0 g of bis-ether. Ta. Epoxidation with m-chloroperbenzoic acid and subsequent trifluorolysis as described above. Reductive ring opening using lithium ethyl borohydride yielded 4.00 g of oil. accomplished.

NMR (CDCIs): 4.49 (d, IH), 4.23 (s, IH), 3 ．． 96 (wide A, l H), 3.5-3.2 (m, 8H), 2.12 (wide, I H), 1.95 (m, 3H), 1.55 (dat, LH), 1.17 (t, 6 H).

MS (CI): 231 (M+1), 259.185゜IRIVc: 7-Oxabicyclo[2,”2.1]hebutane, 2,3-bis(ethoxymethoxy) ci)-5-(phenylmethoxy)-, [2exo-(2alpha.

3 alpha, 5 alpha)] - As described above, 7-oxabicyclo[2,2,11hebutane, 2,3-bis( ethoxymethoxy)-5-(phenylmethoxy)-, [2exo-(2alpha , 3 alpha, 5 alpha)]-(00.5 g 2.17 mmol) in sodium hydride When combined with benzyl bromide in the presence of lium, 0.40 g of colorless oil was produced. .

NMR (CDCIg): 7.33 (m, 5H), 4.52 (m, 4H), 3 ．． 75 (dd, LH), 3.5-3゜2 (m, 8H), 2.0-1.7 (m, 4 H), 1.21 and 1.20 (t, t, 6H).

Add 25 g (0,50 mol) of isoprene to 50 ml (0,50 mol) of isoprene cooled to 0°C. 26 mol) of maleic anhydride was added portionwise. Warm the reaction mixture to ambient temperature , and stirred for 4 hours. Excess isoprene was removed in vacuo to give 40.5 g of It gave a white solid, mp 6'3-65°C.

NMR (CDCIs): 5.70 (wide, IH), 3.45 (m, 2H), 2 , 50 (m, 4H), 1.81 (s, 3H).

IR (KBr) + 2900.1840.1770.1445.1235.96 5.920.800° Add 300 ml of tetrahydrofuran at 0°C while keeping the reaction temperature between 0°C and 5°C. Add 16.0 g (0.42 mol) of lithium aluminum hydride in portions. Ta. While keeping the reaction temperature between 0°C and 10°C, 33.0 g (0.20 mol) of free 100 ml of water 4-methyl-4-cyclohexene-1,2-dicarboxylic acid The solution in lahydrofuran was added dropwise over a period of 2 hours. Bring reaction mixture to ambient temperature Warmed and stirred for 2 hours. The reaction was cooled to 0°C and added with 35 ml of acetic acid. Add chill dropwise followed by 35ml isopropanol and 35ml water. Added dropwise.

The reaction mixture was filtered through Celite using acetone and dried using MgSO. Dry and concentrate to 33.0 g of oil. 3:1 hexanes: ethyl acetate 1,1-hexanes followed by ethyl acetate, and finally only ethyl acetate, Flash chromatography in a column gave 18.2 g of oil.

NMR (CDCl2): 5.35 (wide, IH), 3.68 (m, 2H), 3 , 10 (wide, 2H), 2.05 (wide, 2H), 1.64 (s, 3H).

IR): 3500-3100.1730W, 1440.1010° MS (CI): 157 (M+1), 139.121° Stage C: 2-end , 4-exo-(±)-4-hydroxy-5-methyl-6-oxabicyclo[3 , 2, 1] octane-2-methanol at 0°C while keeping the temperature below 8°C. ．． 0 g (0,124 mol) 400 ml salt of 55% m-chloro-perbenzoic acid 19.4 g (0,124 (mol) of (±)-cis-4-methyl-4-cyclohexene-1,2-dimethazole was added over a period of 15 minutes. The reaction mixture was warmed to ambient temperature and stirred for 24 hours. Stirred. Cool the reaction to 0°C and add 30ml while keeping the temperature below 8°C. A saturated aqueous solution of Na, S, and O was added. The reaction mixture was dried using MgSO4. , filtered and concentrated. 3:1 hexanes: ethyl acetate, 1:1 hexanes : For flash chromatography in ethyl acetate, then ethyl acetate only. This gave 6.1 g of an oily solid.

NMR (CDCIs) + 3.80 (wide, 2H), 3.60 (wide, IH), 3, 45 (d, 2H), 2.70 (wide, 2H), 2.42 (wide, IH), 2.0 (m), 1.5 (m), 1.33 (s, 3H).

IR): 3400-3200.2900.1450.1400, 138 0.1060.1000.820゜MS (CI): 173 (M+1), 2 13.155゜pig p: (±)-2-endo, 4-exo-4-hydroxy-2 -(methoxymethyl)-5-methyl-6-oxabicyclo[3,2,1]octa 60% sodium hydride washed with 1.45 g (0,036 mol) of hexane. 100ml of tetrahydrofuran was added to the thorium. Cool the reaction to 0°C, and 6.1 in 70 ml of tetrahydrofuran while keeping the temperature between 0°C and 5°C. g (0,035 mol) of (±)-2-endo, 4-exo-4-hydroxy- 5-methyl-6-oxabicyclo[3,2,1]octane-2-methanol to 4 Addition was made in full over a period of 5 minutes. Warm the reaction mixture to ambient temperature and add 2.5 ml (0.04 mol) of methyl iodide was added. Another 1.0g (0,025 mo ) of 60% sodium hydride and 2.0 ml (0.03 mol) of iodide solution. Chill was added to the reaction. After 48 hours, the reaction was cooled to 0°C and 25ml of water was added.

The reaction mixture was extracted with ether and then methylene chloride. -The combined organic layer Dry with MgSO4, filter, and concentrate to 7.26 g of oil.

3:1 hexanes; 2 by flash chromatography in ethyl acetate ．． 0g of oil was given.

NMR (CDCId: 3.80 (m, 2H), 3.60 (wide 21H), 3 , 32 (s, 3H included) 3.20 (m, 2H), 2.40 (wide, IH), 2. 18 (m, IH), 2.10 (d, IH), 1.50 (m, 3H), 1. 33(s, 3H).

MS (CI): 187 (M+1), 204.160.155゜Content: (± )-2-endo-2-(methoxymethyl)-5-methyl-6-oxabicyclo[ 3,2,1]octano-4-one 21, 0 ml (0,042 mol) of methane chloride 4.2 ml (0.06 mol) of 2M oxalyl chloride in solution at -78°C Dimethyl sulfoxide was added. The reaction mixture was stirred for 15 minutes, then 10 ml of 3.9 g (0,021 mol) of (±)-2-endo,4-ethyl in methylene chloride xo-4-hydroxy-2-(methoxymethyl)-5-methyl-6-oxabisi Chloro[3,2,1 cooctane was added liberally and the reaction mixture was stirred for 45 minutes. Ta. Add triethylamine (16.5 mL, 0.12 mol) completely and The reaction mixture was allowed to warm to ambient temperature. Water (50 ml) was added and the reaction mixture was diluted with methylene chloride. Extracted with water, dried over MgS04, and concentrated.

3.1 Hexanes: 0 by flash chromatography in ethyl acetate ．． 96 g of oil was produced.

NMR (CD, CI g): 4.10 (m, 2H), 3.34 (m, 5 H), 2.69 (wide, IH), 2.5-2.0 (m, 4H), 1.80 (d , LH), 1.34 (s.

3H).

IR (NEET): 2920.2870.1720s, 1445.1105.9 75° MS (CI): 185 (M-)-1), 202.199.216° glare F: (±)-2-endo, 4-endo-4-hydroxy-2-(methoxymethyl )-5-methyl-6-oxabicyclo[3,2,1]octanetetrahydrofura 2.2 g (0,012 mol) of (±)-2-endo, 4-endo-4-hyron in droxy-2-(methoxymethylcin-5-methyl-6-oxabicyclo[3, 2,1]octan-4-one with a slight excess of tetrahydrofuran at -78°C. During the run IM lithium triethylborohydride was added. After 5 minutes, 10ml of water was added and the reaction mixture was allowed to warm to ambient temperature. The reaction mixture was extracted with methylene chloride. Removed, dried over Mg5O, filtered, and concentrated. 1:1 hexane vinegar Flash chromatography in ethyl acid produced 1.2 g of oil. .

NMR (CDC13) + 3.83 (wide, 2H), 3.40 (m, LH) , 3, 32 (s, 3l-(), 3.20 (d, 2H), 2.40 (wide, 1 H), 2.05-1.9 (m), 1.52 (d, IH), 1.34 (s, 3H ).

Step G: 2-endo, 4-endo-2-(methoxymethyl)-5-methyl-4- (phenylmethoxy)-6-oxabicyclo[3,2,1]octane tetrahydride Sodium hydride being washed with 0.12 g (3 mmol) hexane in lofuran 0.35 g (1,8 mol) of (±)-2-ethyl in tetrahydrofuran. 4-endo-4-hydroxy-2-(methoxymethyl)-5-methyl-6 -Oxabicyclo[:3.2.1]octane was added. Add water and mix the reaction mixture. Extracted with ether, dried over Mg5O4, filtered and concentrated. 20:1 Hexanes: Flash chromatography in ethyl acetate produces an oil. did.

NMR (CDCl s): 7.32 (m, 5 H), 4.62 (d, I H), 4.42 (d, LH), 3.82 (d+dd, 2H), 3.32 (s, 3H), 3.2-2.2 (m, 3H), 2.39 (wide, IH), 2.03 (d t, IH), 1.8 (m.

2H), 1.49 (d, IH), 1.37 (s, 3H), 1.25 (m, IH ).

NEET to IR): 2900.1450.1360.1080.1000.960 ．． 850.730.690° MS (CI): 277 (M+1), 294゜diethyl dicarboxylate 25 g (0.14 mol) of ketomalone in 50 g (0.70 mol) of isoprene Diethyl acid and 0.78 g (2.4 mmol) zinc iodide were added. reaction mixture The mixture was stirred at room temperature for 48 hours. Excess isoprene was removed under vacuum. 20・ 1 Hexanes: 12 g by flash chromatography in ethyl acetate of oil was produced.

NMR (CDCIs): 5.40 (wide, IH), 4.34 (m, 2H), 4, 28 (q, 4H), 2.58 (wide, 2H), 1.75 (wide, 3H), 1.29 (t, 6H).

MS ((, I): 243 (M+1), 283.225.169゜0℃ 4.0 g (0,105 mol) of hydrogenated acid was added to 200 ml of tetrahydrofuran. The aluminum lithium was added in portions. 12.5g (0,052 mol) of ( ±)-3,6-sihydro-4-methyl-2H-pyran-2゜2-dicarboxylic acid di A solution of ethyl in 60 ml of tetrahydrofuran was added in bulk over a period of 30 minutes. . The reaction mixture was warmed to ambient temperature. After 2 hours, while keeping the temperature below 10℃ , the reaction was cooled to 0° C. and then added with 30 ml of ethyl acetate, 30 ml of isopropylene. Lopatur and 30 ml of water were added. Pass the reaction mixture through Celite. Filtered with 100 ml of chlorine, dried with MgSO4, and concentrated to an oil.

Flushing in 1:1 hexanes:ethyl acetate and then ethyl acetate only. Shuchromatography produced 5.5 g of oil.

NMR (CDCIs): 5.42 (wide, IH), 4.18 (wide 72H), 3, 7 Hd, 2H), 3.65 (d, 2H), 1.84 (wide, 2H), 1.7 (s.

3H).

IR): 3000 wide, 2900.1435.1380.1110.10 20° MS (CI): 159 (M+1), 173.141.127゜Sabicyclo [m of 3,2,11 octane-1-methanol 11.0 g (0,035 mol) -To a 55% suspension of -chloro-perbenzoic acid in 100 ml of methylene chloride, 100 ml of 5.5 g (0,035 mol) of (±)-3,6-cyhydro in 1 methylene chloride -4-Methyl-2-H-pyran-2,2-dimetatool was added. reaction mixture Warmed to ambient temperature. After 20 hours, the reaction mixture was cooled to 0°C and 3Qml A saturated aqueous solution of Na, S, 03 was added dropwise. Dry the reaction mixture over Mg5OJ. Dry, filter and concentrate. 1:1 hexanes:ethyl acetate and then Flash chromatography in ethyl acetate alone yielded 1.7 g of oil. was generated.

NMR (CDC1s) + 4.13 (d d, LH), 4.08 (d, IH) , 3, 86 (m, 2H), 3.78 (d, IH), 3.62 (d, IH), 3 ．． 45 (d, IH), 2.22 (d, IH), 1.40 (d, IH), 1.40 (s, 3H).

MS (CI): 175 (M+1), 192.157° 5-methyl-2,6 - Thioxabicyclo[3,2,1]octane 0.3g (0,007mol) 60% sodium hydride in tetrahydrofuran, 1.2% in tetrahydrofuran g (0,007 mol) of (±)-exo-4-hydroxy-5-methyl-2, Add 6-thioxabicyclo[3°2.1]octane-1-methanol, then , 0.6 ml (0,013 mol) of ethyl iodide was added. at ambient temperature After 24 hours water was added and the reaction mixture was extracted with methylene chloride and MgS Dry over Oa, filter, and concentrate. For flash chromatography As a result, oil was produced.

NMR (CDC1x): 4.18 (dd, IH), 4.09 (dd, IH), 3.95 (d, IH), 3.80m, 2H), 3.65-3.4 (m, 4H) , 2.20 (d, IH), 1.50 (d, IH), 1.40 (s, 3H), 1 , 19 (t, 3H).

MS (CI): 203 (M+1), 220.185° Step E: (±)- 1-(Ethoxymethyl)-5-methyl-2,6-thioxabicyclo[3,2,1 ] Octanone-4-one 4 ml (0,008 mol) of 2M oxychloride in methylene chloride 0.7 ml (0.01 mol) of dimethylsulfate was added continuously to Salil at -78°C. sulfoxide, 1.2 g (0,0058 mol) of (±)-4-exo-1-(ethyl toxymethyl)-4-hydroxy-5-methyl-2,6-thioxabicyclo[3 ,2,1]octane and 2.79 ml (0°02 mol) of triethylamine added. The reaction mixture was warmed to ambient temperature and water was added. Chloride the reaction mixture Extracted with methyl, dried over MgSO4, filtered and concentrated. flash Chromatography produced 1.0 g of oil.

NMR (CDCIs) + 4.50 (d, IH), 4.21 (m, 3H), 3. 57 (m, 4H), 2.20 (d, IH), 2.10 (d, IH), 1.40 ( s, 3H), 1.21 (t, 3H).

Step F: (±)-4-endo-1-(ethoxymethyl)-5-methyl-5=methy -4-(phenylmethoxy)-2,6-thioxabicyclo[3,2,1]oc Tan A slight excess of lithium triethylborohydride in tetrahydrofuran At 78°C, 1.0g (0,0049 mol) of (±)-1=(ethoxymethane) methyl)-5-methyl-2,6-thioxabicyclo[3°2.1]octano-4- added. After 5 minutes, water was added and the reaction mixture was allowed to warm to ambient temperature. reaction The mixture was extracted with methylene chloride, dried over MgSO, filtered, and concentrated. to give 0.5 g of oil. 0.2 g (0.97 mmol) of this oil contains tetra 0.1 g (2.5 mmol) of 60% sodium hydride in hydrofuran and 0.25 g (1.5 mmol) of benzyl bromide was added. 24 at 60℃ After an hour, water was added, the reaction mixture was extracted with ether, dried over MgSO4, Filter and concentrate. 20:1 hexanes:flashk in ethyl acetate Romatography produced 0.38 g of oil.

NMR (CDCIs) + 7.32 (wide, 5H), 4.55 (s, 2H), 4.00 (d+d, dd, 3H), 3.68 (t, LH), 3.40 (m, 4H), 3.38 (dd, IH), 1.79 (dd, 2H), 1.40 (s , 3H), 1, 18(s, 3H).

Hydroxy-7-oxabicyclo[2,2,1]butane-2-methanol 10 26.5 g (0,146 mol) of 2-(1-ethyl-1) in 0 ml of acetone -hydroxy-propyl)-7-oxabicyclo[2,2,1]hepten-5- 17.6 g (0.15 mol) of N-methylmorpholine in water at 0°C. N-oxide and 10ml of 4% osmium tetroxide were added. Circulate the reaction mixture. Warm to ambient temperature and stir for 4 days.

A saturated aqueous solution of N a 2 S 20 s was added. The reaction mixture was diluted with ethyl acetate. Extracted twice, washed the combined extracts with water and brine, and dried over MgSO. Dry, filter and concentrate. By flash chromatography, 12, 0 g of thick oil was produced.

NMR (CDC1s): 4.44 (s, LH), 4.38 (d, IH ), 3.85 (m), 1.8-1.7 (m), 0.84 (t + t, 6H) .

MS (CI): 217 (M+1), 234° Stage B: (±)-exo.

exo, exo-α, α-diethyl-6-[(2-fluorophenyl)methoxy go-5-hydroxy-fuoxabicyclo[2,2,1-cohebutane-2-methano 1.2 g (0.03 mol) of 60% sodium hydride in tetrahydrofuran at 0°C. To thorium, 6.0 g (0,028 mol) of (±)- in tetrahydrofuran exo, exo, exo-diethyl-5,6-pishydroxy-7-oxabisi Butane-2-methanol was added to chloro[2,2,1]. Bring the reaction mixture to ambient temperature and add 3.4 ml (0.03 mol) of 2-fluorobenzyl bromide. I got it. After 24 hours, water was added and the reaction mixture was extracted with ether and purified over MgSO4. dried, filtered and concentrated. By flash chromatography, 1 ．． 3g of oil was produced.

NMR (CDCIg): 7.5 7.0 (m, 4H), 4.69 (d+d, 2 H), 4, 50 (s, IH), 4.40 (d, IH), 3.92 (d d, IH), 3.61 (d, LH), 3.20 (d, IH), 1.2-2.0 (m ), 0.80 (m).

MS (CI): 3.24 (M+), 342° Step C: (±)-Nixo, exo, exo-5-(1-ethyl-1-methoxy-propyl)-3-((2- fluorophenyl)methoxy)-2-methoxy-7-oxabicyclo[2,2, 1.3 g (4.0 mol) of (±)-ethyl in butanedimethylformamide to 11 xo, exo, exo-α, α-diethyl-6-[(2-fluorophenyl)methyl Toxico-5-hydroxy-7-oxabicycloc2.2.1]butane-2- To the methanol was added excess sodium hydride and methyl iodide.

The reaction mixture was stirred at 70°C for 12 hours. After aqueous treatment, chromatography 0.25 g of oil was produced.

NMR (CDCIg) + 7.6 7.0 (m, 4H), 4.71 (wide, 2H ), 4.45 (s 10 d, 2H), 3.66 (d, IH), 3.52 (d, IH ), 3, 52 (d, 18), 3.42 (s, 3H), 3.15 (s, 3H ), 1.8-1.2 (m), 0.80 (m, 6H).

MS (CI) + 353 (M+1), 370.338゜Table 1-5 is the present invention Examples of types are shown. These examples mentioned are encompassed by the present invention. It should be understood that these are merely illustrative of the range of types that may exist. The symbol rPbJ is means phenyl group. The compounds in Table 10-15 have WCH, O groups that are oxygen-containing crosslinkers. y>. End/Kytrogen mustard symbol is C ( R3XR') refers to the structure of the OR5 group. The ratios shown (Table 10) are Compound (I) of formula (18) is formed in an inseparable mixture with a compound of formula (18) It refers to the case. The ratio is shown in the form (I:(18)).

Exo ((♂) (f) α-endo-east “Xll’) 01♂ The types in Table 1-8 are from this product Ming ceremony! -vIII compounds. Therefore, not identified in Table 1 The first compound (RI=H, R2=H, R3=CH3CH2, R4=CH, Cm , R' = CHs, and W = 2-FPh) are identified as formula (I) It is a type of compound.

Table 1 Cl, CH2C11130f20f3C1!2(2-ffh)! 10130f 2CB3C12Chi, CB2(3-rPh) BC1130f2CB3CII 2CI! 3C! ! , (4-rPh) IfCH,0112CI! 3012CH3 (:ll2(2,3-F2Ph) If013Q+201,0i2cE30f2 (2,4-F2Ph) 1f013012C1113c'l12013(B12 (2,5-F2Ph) Eot3am201,012011.012(2,6-F2Ph) !lCH3CB2 CB5CH2CH3CIi2(2 -cIPh) ICI, 012013cB2cE3012 (3-C1Ph) Hot3oi 2 C1l, CB2 01.012 (4<1Pb1 H0!, 012 013 Of2 0I3 C112 (2,4-Cl2Ph) BC113C112013 0f2C H,ax2(z,5-cx2ph>* 0f30f2013Chi2( !30f2(2-Br!'h) !ai3ai2013Of201.012( 3-Bri'h) ECB13CH2CBzCIi2 CB13 CH2(4-BTPh) !jcB30120f3012CIi3QI2(2 ,4-Br,Pk) HCl13C3i2 CH30f2 C213C112(2,6 -Br2 Ph) !ICB, CH2eI13C112CM, CH2(2-<On'f!3)l'h) EIC1i301201.C112c113.C'JI2(3 -(OeE3)Ph) ll01.01201301.CH30f2(4-( 屏3 ) Ph) ll013(J CE, CB2 C113CB2(2-(CB, )Pkt) II!'E' R2OX CH3CH2C'1(30I2CH,CH2(2,3-(CH3)2Ph) I N01130i2C1i3Cm21:'R,012( 2,4-(CB3)2f' h) Hol, 0H2C113012013C12(2,5-(C13)2Ph) Bcii, ci2cii3cii2cm3CH2(2,6-(01B, +2 Ph) 1ICI3C12CH3HE2el!, 012(2-(01,C) 11 2 ) Ph) IIα3CH2α3 Punishment 2013CB2(4-(mouth3α2)Ph) HCB3el12C'li, e112CI'113C112(2-(011)P h) HCl1.(E20I3CH2CB, CIi, (2-(Of)Ph) HCB, Q12CE3( J12c1!, CMz(4-(01)Ph) II0!, C112CI4.CI'!2 03 Mouth (2-(σ,)Ph) HCl1 .CH2CB5Cl!2C1i3CM2(4-(CF,)Ph) HCH3CO 2CH3C12C8, CB2(2-((XT31f'h) 11CB, C12C 1'l, C)12C13CR214-10cF3)Pk) IIC13CR2C M3llC13CR2C'+2+2-(Sol,)i'h) Boi, CH2C 113e112 C coH3CJII2(4- (Semi ,)Pkt) HCH3 CH2C13CH2Cll3 CH2(2-(CIHzC! IgC! f) Pb ) HCB3CHz CH3Cl12 CB5C11z(4-(CBzCIi* Cl1)Ph)! 1cm3cm2e113C12ellI3cB2 (z-(i ic=c)ph)tx mouth, 02CH3CIII2 0. Mouth 2 (4-(!1cE c) f'h) HC'ii, L:B2 CIi, CH2CIi, C1!2 (2-pyri9cle) Iris C11,012CH30f2 0f3 01 (3-pyridi Le) Company CM: 5CB2 CH3CH2CH3CB12 (3’7 Ranishi) HC ll3CB2 CH3CB2 C”3”2 (2-(3-C1) Birirakure) IC! +, CI2 Cjl, CE2 0! , Cm2()-(2-C1) Bi Lee, ;/IL/) 8 mouthi, oi2os3oi2C113 rho (2-(3-1!lr)thiophenyl) HCl1. CB2 CH, CB12 01. CH2 (3-(2-total) Gumefuyu≧:,+Lz), Hol, Q12013CHI20 13C! +2 (2-(5-Cm3) furanyl) HCB, CB12 013C 12013CH2 (2-thio7 u4shi) ' 013CB, Of, C'32 am352 (3-f; t7ff-JL') ICB13012 CH30f2 Cil, CIi2 (2-f two-ts” 11 nor)! "Kuchimo 012 C13C H2CB3 011 (2-imida 5^nor) H Rorif, 013CB2-kuchi et al. (2-pyrazyl) HCll3CE2 0f3CH,CB, CH2 (2-#/1 nor) ・ , yi!l' E ' CH5Ω CH, CH2CIi, 012 (2-bi%H:yshi) 101, CICI, 01, Of, OJ HCl, CHCB, CCl2C, Q-2BCll, C112口3α2α, Q-311C113012013CD2elf, O -4H口I, Cl2C!I , 012C113Q-5HCH3CM2CH, CM2 C1, Q-6HCH, 0M2 01I, CH2CR, O-7MOi3C1120 1, Cl112C'lf, O-81IC31, Cl2012Cl12CH, Q -98 mouth 1.C112C1i, 012elf, O JOlIC13C1i2 C Ii, Cl12 0f, Q -111tOf3C'H2C1l13012CII 30J2 !IC0,01201,CM2O13Q-43HeII, e1120 f3CHI□CH30J4 II0+3012 C113012C1130-1 5M mouth I, CM2C1!3Chi2CH3C12 (Ph) Ifol, Cm20 1.CB1201,0120i2(2-FPh) ll01, C1120f30 12 CH30f12 C12(2-CIPh) M1O1,012c11.C 11201,012012(2-!1rPh) lCH3012C13CH20 130!2c!I2(2-((m,)Phl H mouth I, CB2CB5CH201 3c112CH2(2-(OCI+,)f' h) Ifol, ClI2 Lolico 2 Loli:H2CH2(2-(α)Ph) HOf3Cf120130!201 .CH2012(2-(CF,)Ph) IICHI, Cl2C11,012C ji, elf2012(2-(OCT,)Pk+) HCB , Cl2CH301 2CI, Cm2012(2-(BCll3)Ph) i!mouth!, (m□01.(B201.C112012(2-(SC1i,)Ph) ll01, CBCI !3012Cm3CH2012(2,6-(r), ! 'h) H! 13B' C H50X CM, CM2O1, CH2C1 (3C) + 2C) 12 (2,6-(C1)2Ph ) HCEx C112CH3CHz Cll3CBz C112 (2-Pi IJ 9) Hol, °82 °! , CH201,Of2 CB2(2-7,y> shi) BCl3CH2CM,CB2 C11,C12012C2-tetrahydro 7u,) Hci, CH2CB5CH2C11301,012(2-7totrahydro Lopila y) aCC comic 3 c ko 1 C ko ii (ko) 2 C comi 3 (ko iz C ko 〼 2 (2-rajifutof〉) Hcit, ox20t3oi2CI, CIi, 0 12 (2-ia-?l"' /”1)k) BCl3CB2 C1,CIi2 0 1,012 Cl2(2-pillar; wshi1iCH,0112013CM2 01 .C12Cl2(!'h) M1O1,0(01.elf2C!!30120 -I IICH,CM2O1,012CH ,OfQ-311CH31-CIi ,Cm013C1120-611C11,0M2 C1,CR2CH3Cl2 0-7 Bol,Cm201.CB2Cl,0f20-15 1fCl,O1 2Cm3CE20f,0r2012Q2(2-FPh) IICHI, CB2C B2C113C+3C11CB2012 (2-CIF'h) ll01 I f Loli: 112C11,01201,0202口2(2- (α)Ph) Hol, OH□(m, CB2Cl, CB2Cl12Qi2(2- (ff,)Ph) lIC11,e112013CB2+:II, 012012 012 (2-(C7,)Ph) 1fC13012CI, 012 Rorif 2ko2 Mouth 2 (2-(Sol,)Th, 8cB302cH3CIK2 Ro1,012 012CB(2,6-ff)2Pk) Hol, C'! I2 013012 0! , CH2Cl12 012 (2,6-(C))2Ph) ifCM, C12 01, C1201,0! CB2 Cl2 (2-bili%) Hol, Of2 013 (B2 mouth i, CH2Cl12 Cl2 (2-7 Rani J) !IC1i, C!l, 01.Cl120i3C110f2C112 (2-tetrahydro bilane) 11 mouth et al. L: 112 lo Town-52 CH is 1-10 (2-tet (Lahydrobilane) HCB, CH2013CH201, C112C1i2 01 2 (2g birajyl) 0130120I301201. Cll2cE2CO(Ph) IIR] B14 R5Ω , Chi20f30f2C1i, CB2CH2 0-711CHI, 0i12CH3012CH3 (II20f20J5 1fc 113C112CIi3Cj12CB2Cm! -CH20f2(24Ph) I ICH30f2 33CB2 CH121:H, Cl2 CH2(2-CIPh) C013012CH3Cl2 CB2(Hg012 C112(2-!1r Ph) HCB, 012CH3CHI2012CH, CH2CH2(2 -(CB, +Pb) IICH, CH2Cl30f2CH2CI=QI2012( 2-(OCR,)Ph) lIC11zcII2 C113CIi2 c1g201g C1i2 C11z(2-(Of)f'p) 1f0130f2ell, Cl2 C!l2CB, CH20f2(2-(CF,)!'h) iIC113Cm20 1. C112012C!!, Cl2012 (2-(OCr,)Ph) HCl1 3e112C11,0f2C1,C1C11=C1i2012(2-(Se,) Ph) HCl1xO(z Cmxolz C11zOIs=CHz CB12 (2,6-(F)2!'h) HCl3CRz C) +30120!201*C H2C1z (2,6-(C1)2!'h) !ICIxCHz CH3CH12 C51xC51xC11% (2-Bichirin) 5013C112cm3cm2CH2 C!! Snow C12ClIz (Ph) Iris well, 0 12C113C!12C120 1*320 -I ll0130120!, r: 11. 3201tCH2Q-3 11CI3C1120!301z 01201sO1z Q-6H013C1i 2 013012 01201tOI2 0-F Wing ai3oi2oi3ai2 oi2atwot2g-1 s 1Of30120!, C112012CEOI mouth 2 (2-FPh) 101301201.012cyx2c=cx ci2( z- cxph) mC113012013CIi2 (512C=CII 012 (2-BrPh) 1(:!1,012CII, C!I2o12C=CM C!I□(2-(01,)Ph) 1B" E' E5Q X 01, CM2CH3CO2012CECHCH2( z -(ocn3)ph+ H CE3012 C1!3CM2 012CmiC1l 0r2(2-Edo)Ph) BCll, 012C1! ,0H2cyx2c=cs cm2tz-(cy,) ph+! ICB, Cl2C113C1!2cB2CEP! o+2(z-tc cr3>ph) m mouth+, elf2013CM2CB2CECHci2(2-<s cm,>pb> mcm3cm2cB, ci2cmc=cn CB12(z, 5-(r)2ph) Hol, CH2cm3cH2ci2cEcn ci2<2 - 7 ra, i11+113cH2CB3Cl2 C112C=1 2 (2-tetrahydrofuray) mCH3CR2CH3Cl z CM 2 C=mouth CM 2 (2-f tracht b bila y) txC113CB2 C1+, 012 C12Cmi CII Of2 (2-thio7 〉) HCl, CH□ 013CR2 C1!2C MiCI 0f2 (2-Ink Zuichi Hanol) HC113el1201 3Cm2or2c=cs cm, (z-Birajichi ν) HCl1. e112cm 3cm2an2c=ai ci2(ph> 1ICI, C)I□Of, C)12 0I2CEEot Q-1101, C11201, CH2C112Cmi CI Q -3ifachi F iris 2 ci, at2 ot2cmi CHI Q-611CB3CM 2 mouths, Of2 lo 2C MiC Mushroom Q-F HOf, C112CHI30120!2C MiC'! i QJS HC:143cHz CIHiC'S2 口2Pb CEI2 (2-F'Pb) H013C112CIi3012 CH2Ph C1112 (2-CIPk+) 1f013CH20f, C112Cm2Ph C112 (2-1rPh) IIel l, C11,01,C112CB2Ph CH2(2-(01,3I 'h) H mouth I, C12013012012Ph 0f2(2-(OCRI,)!'h) M1O1,012013012Cx2F h 012(2-(Of)Ph) BCll, CH2011,CB2CH2Pb Of2(2-(+73)Fh) IIO!3012c1 13CM2el12P h CEI2(2-(OCT,)!'h) Hol, Cl2C! I, C) 12 mouths m2Ph Cl2(2-(Sol,)Ph) 1telf, CR, CH, 01C! I2Ph CCl2 (2,6-ff)2f’h) CH01,OfC21 3CH20!2Ph CH12 (2,6-(C1)2Ph) C0130120 13CM2 012Ph 012 (2-giri-nkure) II! 131' B10 n, oi2 oi2ph o-) HcR3cm2cys3cm2c'52ph o-1s nCD2012C213C12012α:E3C1i2(2 -F T'h) IIC) +2CM2CH3C112Chi200113CII2 (2 -CIPh) II012CM2013e112C112α:IE3 口2 (2-BrPh) ”α2CH2I:ll300α:1!3CB2(2- (OH3)1)h) llCm 2C1)! 2CH3CB011α:B, 0 12 (2-(α:!13)Pli) H Loli τ2 Ko, Go, 02α Go 3 0 (2-(α)Ph) IICM2CM2 01. CH20120013CB2(2-(CT,)Ph) mIC)I,C)I2CB3C112c112001. CB2(2-(OCF,)Ph) HO212α,σ2 α2α:II, Cl I2(2-(5 mouths,)!'h) Wing CB12CH2Cl3C7(201200!3C12(2,6-(F)2Pki) llCM2C112Chi, Chi2 CHI20C!I, CH, (v with 2-pyra 9) HC'H2CM2O130 12CI (20013012+Ph) BC12C12cE3CM2BCl2C 12cE3Cael12CM2C5':H2Cm2α:H3Q-3F113E' R2OX C11XC 112C,!:'H2C1'!20CH3Q-6HC12CM2 C H3CH2Cl120CE3 0-F HCH20120f, C02C1i20 CE, Q-151ICi1.el12CB201.Cl2CR2C1i, CH 2 (2J!'h) ll013012el12CH, C112C12Cm301 2 (C112C12ClIC1130120i20f3C1i 2011201.012(2-Brf'h) !IC1i, Cm2C112C113CH201 2C1i, Chi2(2-(Chi13)Ph ) IllC113CH2CH 2013C□CM2Cm3C1l(2-(BCB3)Ph) Ho1w012 012(m3CH2CE2C1,OH2(2-(CI)I'h) 1(c+1!3012CM2CH3CJ2C)I2CB3CB2(2-(CF3)P h) !ICM3CEC1(2013CM2C1(CF 01(2,(OCF3) Ph) BcH3C12CM2CR3CEC)I2Cd, C'B(2-(Sell,)f'h) 11CM3C112CM201.CC112C013 CByo(2,6-ff)2Ph) 11CH3CE2CM20130!□CH2 01,CB2(2 ,6-(C1)2Ph) Hco, cH2c112oi, cB 2oi2oi, C1l(2-chikuri BCH3CH2CH2013Chi2 Cm -pyrazinyl) IIC!13C112 C112CB, CB2C112(:i, CB2(1'h) H013CB, CM□ell, C11201201, O-11101, C112CB2 Ca13 Chi2012 0+, O-3!0130!20!2CB, O!2C!I 2C m30 -6 IfCHI3CH201201,012CB20130-7! 0 113C1120120!30120120130J5 II0!3C112C B201,012C11CI! , 011201. (Ph) IIG! 3C11 201201,0f201201,012CB2(!’h)! ICH, Cm2 0I2ell, Chi2012Cm2Pb CB2(Ph) IIO! 3(11 2C112CR2C11301, CH2(820113012(2JPh) l ll0!3CB, CP+2C1i20f, C'!l2C11!2C'H2CE3 CR2(2-CIPh) Hol, C!!2C12012Cm3012CE2C 11201 3CH2(2-BrPh) HB3!l' R5OX C11 !31232CH2 Punishment 3012CHI2C'H43 C2(f'h) ll013CE2012012C)I, C112C1l120!2CR3QJ I IIas3cn2o+2o+2 α3α2α2α2.01.O-3H0 13CM2CRCBO!, CM2CE20 1!2Ca13QJ iICM3 C12012C'H2013CB2("E2CE2 01.Q-) HCm, CI'IC'R, (B2C1l13012CTI2CE2013QJ5 RC i13Ci12CM2e112CM3CH2CH2CB2CM, (ll012( !'h) RcH, CM, Chi2CHI30f2 (2-F?h) IfC!!3013CB201.0N 2(2-C)Ph) HCl13013CIII2 03 02(2-( C1 (3) Ph) BCB3 CM, C11201, OH2 (2,6-C 2 Ph) ROf, CM3012 01.012 (2-Billy - Jill) 11cE3CB3CB2C1! , 012(Ph) R013CB3 Cm2C1,QJ B 13R' B10 M CH3CM3C) I2CI (30-3kiCH30i3C)! 201. Q-6H C'11301,012elf3Q-7HCH, CB, Cm2 mouth 30-15 B O! 2C'BI-CI, 0i201. ClI2 01. Chi2 (24Ph)! IC1zCHgC12oi2CM-CH2C:B3 CEz (2-(l Pb) HC12CM-CM2CB201gOi2cx, 01z(2-(Ol x) Ph) IICR2CH*(m2012C1igC)!2013CT+2(2,6-Cl2P h) HCM2Cll-CH2(:)1!2CI II (: FI2 CB3 ClI2 (2-Bilisifre) Rα2CH!l:+(232c Tomigo203 C2(1'h) 110(2CH, CH2Cl1m1.Chi2C O3Q-1!ICH2cn*C:142 0z(:5i*l) 2CB. rib) 1 bite 1.0!2CIl*CH2C113CI!2 (2-CIP h) 11CF!=, CH2Cl1.01Cl13CR2 (2-(C'H3) !'h) 11 mouth 1=c112CB, CE20f3012 (2,6-Cl2Ph) Ho1w1012 ql -C12013CB2 (2-pyridyl) Ill: 1 !FuC112 mouth Mko 201.Cl12 (!'h) ll011-CFI2 C 11t012 013 Q-I H low 〇12Q1.Cl1201.Q-3H 01-012CHsO12013076BCB-CH 2CE*012 CH30 -F HCB, CB2 0!, CH20130J5 !ICH2C=CH012 CECH01,ox2<2-rpb)ysOI2c=cHC111C=CII ct3cmtz-cxph)mCE2CC2CH2I ca2cEoi C H3o+2+ z-(Ca3)ph) m313R' E5Q X cE2c=co CM2C3 C1 (CB3 CB2 (CB3 CB2 (2,6 -CL2PH)) HCM2C = CU CI2C = A! AY3, (2 -Billy, 2I) EI C112C Mimon CHCH20CII CM, CR2 (PH + IICYS2C = CG OX2c = CYX C1L , O -111QLCEC 'Hci'+c= or 01.O-31!cH2C:Cm C)I2c=o+ Cl13o-a!!elf2Cmics C112a=Cs 013 0-fu HCll2c= cHcy2c=011 CM, Q-1511cH2α':HCl20CR30 1, 012(2-rPh) ItC′If2α13 α2α13 α3C12( 2-CIPh) m1C10CR30120011,CH3Cl,+2-(C Ii,)l'h) IICH2QC)i, 01200130f3(B2(2, 6-C12! 'h) HCl120C1! , Cl120CR3CH,C112 (2-CF, Ph) HCl20CR3C1200! , 01. cll, (2-f trahydrobirane) mcH20013ell, 0C1l, CB, C' R2 (2-Billy;) b) HCM200 (, CH20CR, Oi, C112 ( Ph) Rco2ocn3 α2α:B, Cl113QJ HCl20CR3 s3c Mouth, Kui, Mouth 20CIII30130-6 80120CIi3 C1200!, 013 0-7 HCl3CH,cF120013CH,Q-15II Loli: 1i2B CIi3 α2(2-Fl'h) Ii013C1i21i (m3 C112(2-C1!'h) ICE 3CIi2 Ii Chi, Cm2(2 -(C11,)Ph) 1ICI!3Of2HC113012 (2,6-Cl2 Pb) HQ13C112II 013012 (2-ff, Ph) R013C B2 B C213Cl2 (2-tetrahydrobilane) IICR3CM2 HC ll3 CHI2 (2-e+), )t ) Buy CM, CR2B CR3CE2 (Ph) lll0+301H0130J B CH3Cm2 II 0!3 Q-311x3 B4 ES Ω 15 iI 012 ( E12CH3HC1l, 012(2Jf'hl H012012013 II 0f3C12(2-CIPh) H012CM2Cm, it C113 C112(2-(013)Ph) llCB2CH2Cm3 Ii Cil, Cl2(2,6-(Yu2f'h iIel12CH2C'ji3R0130!2 (2 -CF3Pb) ll0i, C1C112CHC11301, (2-tetra Hydroviran) HCB2CH2C! ! 3 HCE3 CTlz (2-Billy Di ) IKCH2Cm, CB3 HB13 0!2(!’h) llCM2C! I □CH3H013Q-L HCm2C12CE3 HCHI, Q-3HCl2 CH, Cm3 II CHI3 Q-6HC3C! l2C1i, HOf3 0-F C112C12CH, I CHI30-15 C013C CE3CM2C1i2CR2II! 0f3CE2(2-CIPh) 1101, Cm2CE2CH2! ! Of, CIi,+2-(01,)f'h) HO f,CI(2CM2(B2 H CH3 0!2(2,6-Cl2Pb) HC B,0f20120!2If 0!, CHI2(2-Cr3Ph) C013 CIi2cH2CB2 H Ql, CE2 (2-5-trahydrobilane) y xol, CM2el12CH2 H cB, CH2 (2- a little bit) Ho l, 0!, C112CH2 if 013 012 (Ph) Hat3cx2c a2o+2 ic comic 3 0 -I lICll3CB20f20f2II 0 130-3 C013012CIi2CH2 1i 013 0-6 B '0 13C12CE2cB2I CHI30-7 HCl13012C112CB2 H 0130-15 ll01, CE3CB30r2 (2-rPh) HCl 3CH, 013CE2 (2-(lPhl 1!c1113 0f3 0!, (ko12(2 -(CB3)Ph) I!!l'B'E5Q H CB3 CH3 CI(3 CB2(2.6-C12!'h) C013CH3 CH3012(2-CF,!'1111 11CH3 CE, CH3 C11 2(2- f to-y hydropyran) HCHI, C113 CIi, 0i2 (2-biliracle) Hol, 013C1i, C1l (Pb) HCB, C1l, 01130-I HOf3 C113 CI'f, O-go 8 mouths CB3 CR3 0-6 C 013 (B3 CB3 Q-7 H CI(3 0f, C13 Low 15 B1" B2 Komi3 breath'!+5 0 XCR3 CB3 II H CB3 CB2(2-FPh) R mouth!x C 'H3R Fl 01+, C112(2 -(:1Ph) !!-013 CB 3 H II Chi, C%(2-+1rPh) EC8, 0113 1 H CH3 012(2-α:H3)Ph) HC1!, 0f31 HCH, C112(2-(α :H,) Ph) IICB3 C1 (3 Ii B C1 !3 012 (2-(mouth 1) Ph) 11C0. 0! , B II CH, 012(2-((7,)!'h) HCl3 0!, H H CB3 C1!2(2-(OCF3)I'h) C013 CB3 FI B C11, 01 2(2-( Sol,)Ph) BCH, CI, FI H cII3 0+2 (2.6-ff)2Ph) IICB, 01, FI II C+13012 (2,6-(C1)21'b) IIQl, cll, II 11 0+, cm Yo<2-t Risil) 11C8, CB, HB CF13 Mouth! , c2 - 7-7, +shi) HCl1, 01, II If Of, C112 (2-tetrahydrofura7) mOf, Of, Xi ylol, CH3 H H CH3 0f2(2-f'>do Aconi = J) B5, C1l, B H CH, Cl2 (2- I7 1nor)! ICHI, 01, H H CB3 CH2 (2-pillar)w shi) HCB, 0(, H 11 CB, C11z(!’h) HxI B 2 E 3 x4 x5 Ω XC) I3C)! 3H H CM, Q-I HCH3CH3III FI CM, Q-3 1! Of, CH3I H C 1i, Q-6 HCl1, CM, H H oi3 0-F H loco CH I3 H H CH, QJ5 HCl3 CB3 11 if C8, CB2 C’! l2(2-rPh) RCHz C+13 FI H CH3CR2 ll+ll2(2-CIPh) FfCfl, 01,III II 口3ko2 CE2(2-(country,)f'h) 1tel, CH3I H C11312 口2(2.6 -r2Ph) aCIO, 01, H Fi C113C12CB 2(2-+1rPh) ll01, CHl3II +1 0! , CB2C1!2+2,6-Cl2Ph) HCl3 CH3 H H CH, CB2 CB2 (2- It's so hot) HCl1301, ! ! H 01, CH12CR2 (Ph) Bα3C83H H Loli: 112Q-1HOf3C1i3H H c II, Cl2Q-3 HCl1, C Town II E CH3Cl12Q-6 II CH3CM3HH C1l, C1120-7 IICB, CB3 B I I Of, CH2 0J5 ll013 Q4, B H C112C11. Oi2 Cl12 (2-n’h) HCE, C’83 iI H 口2CH 012 CH, (2-C1l’h) HcB, CB, 11 1 CHzCHtO1 2Q! z(2-(Ql,)Ph) 1101, CH3I H 0120Ia0 120!2+2.6-Cl2Ph) C013 CB3 1!11 Ql20 1. CR2 012 (2-(T3Ph) !mouth-ra mouth-ra II H α201, +.C1!, 01, (2-tetrahuman 1 cholan) HCB, Ql, if 1!C1201.0I□ 012 (2-H bili) x )! IC1i, C1 1t, if H e112CIi. (li,012(Ph) 1lQi, C PI, II I CH2C11mC+12 0-1 yxcB, cH, H FI Cl2C11.CH2 Q-3 IIQi, l:lH, B iI 0i2("1-0120-6 +1cy1, C113 B II OI2CB mOI20-) Eot, cII, llIn Cm20!mc1i20J5 !II:II, 0f3II H el12Ph C112(Ph) iIc 113CH3II B CB2Ph 02(2-FPh) H!+” B2It 3E' B5OX CR3CH3HR012Ph C1i2(2C112(2- (CHCH3Cl3 l H012Plz C1!2(2,6-Cl2Ph) Bol, Cl3l B CB2Ph O-3mCB, 01311 II Cl12C!iSiRo3) C2(Ph) 1101, 01311 11 01201=CH(CI,) C H2 (2-ffh) HCl3 0f3 mI n Cl2ell 01(C' B,) CC12(2-(C'H3)Ph) lIC113CB3 !!II ex2cfi-oi(oi3) Cl12(2,6-Cl2Ph) 11α3 Cff3! i II CB2O to 3) Q-3HCl30(3,HII ( :'E+2001.CB2(Ph) HCH,C11311HCB,0013 C1i2(2-Ff'h) HCM, (J13H1!CM001.CR 2(2-( Cm3)Ph) HCal, Cl3l II CE20C'EI, C112(2J-C12P'h) iIC1i3CM3HHC1120013 0-3lllCl, CM3CM3CM3C1!, C112(Ph) HCT (,013013C1(,CH3Cl 2 (2-FPh) iICI (30130 13HM, C113CD2 (2-(CHI3)Phl ItCM3CM3C13 C1i, C1l, CB2 (2,6-Cl2Ph) HCM3CFI, C13 CM3C11C13CHCH3CB3 CB, CM, 01.CB3 012 (Ph) IC'H3c+83C1'!3C113G 1,0!3C1l!2(2- tPh) El(m, Chi30!, 01.0120!, 01(2- <0f3)Ph) HCl3 (B3 C13013C112013012(2,6-Cl2Ph) !IC) f3CH3C113CII3o12CB30-3 HOf, Of, 0i20 !2013C! 13CH, Cl1l, (f'h) 11013CD3cH2Q12013CH3013CD2 (2-rPh) H I03 Hit 3CH20233G3 G3 C2 (2-(mouth 3) f'h) HcE 3Cl, 0f201C113Cl, CB, CH2(2,6-(l □Ph) lIC13CB3C120f2el13013CH3Q-31IC12C13 CH2013111!CH3Cl2(Ph) IICR2C'H3α2α, i it α, CHI2(2-rPh) l'ICR20I3C'H, Cf13 II I CIl!, CH2 (2-((:113)Ph) BC1i2CM3 CH2C13HII CH, C2(2,6-Cl2f'hl [1R' E2B 3B' B5OX CH2Cl30I2C C12HlmCl2CH3C H CFI2m113012(Ph) ifCh i2CM, CH2Cl, )l H O12Cm3CR2(2-n'hl 8 mouth 2H HI, C1iα, Yo R 0 mouths 3 mouths 2(2-(mouth,)Ph) I I012CO12C113012C H CH2Cl3(il2(2,6-C1 2P'h) IIe112cH3c'E2cE, H II C12P'h, Q-3 !1el12CB3 CH2C"B3 11 H o12cmgc g2 012 (Ph ) iIO(2HM, 0!2CH3H H 0N2C1.1J 2C!l2(2-rPh) HCH20!3 0f20i3H R CH2CE 寥CH2 01z(2-(CRa,-”hl HCl(2C1(3CH20f3 H if CB2CRmCE z C11z(2, 6 -C1ZPH) 11HH2 Go 3H1F2HM3II B C2HB + CM2 0-3 1HM2C) I, 012HM3 G3 G3 CH3 3 Exit (PH) II Lori: "H, CHI 2C1 (3 OF3 Exit, C2 (2 -Key) H012C11, H012C11, C1' l□CH, CB, 0f30i3012 (2-(ell,)Ph) II mouth I , Cm, C'H2C'H3CH, C13CR, CB12 (2,6-Cl2 Ph) 1lC1!2C13C1201, CHI, 13 mouth, Q-Go H CM0!301201, C1!,012CHI,0f2CB2CE, CB, 012(Pb) if012CM3012Cii3C112020 et al. 02 α2C1, CB, C2 (2-FPh) 1l1012C, CB2CB50! ,0f2C133,C112CI, 01, CHI2(2-(mouth*,)Ph ) 11CH2cH3 Cm2CFI3 CH2Cl2CB, G12C120 1, CH3 0f2(2,6-Cyu2PTh) Ifel12(R3CB2α 3 020 riff 3 α2 CB2CB, mouth, Q-3 itl CBsCH2C HzC:Es C11zC:ll3CHz CH2(!'h) ItXI CB .CB2012(H3Ci12CB, CHI, 0N2(2-FPh) II Ij (:B.012C3i2CB, 01201, 01, CH2(2-(C1i,)Ph ) III CB5C112 CBzCEs 012013 C 113 CH2 (2,6-Cl2Ph) HEI CXiw-CJlz C:H 2C:B3 C11lz(:Ez C113 Q-3 Bii c=co oi 2oi, mouth 203 03 Mouth 2 (Ph) l1Hc= cx Cl2CO, C H□01, CH, oi2 (z-rph) IIHC Mi Cm 012013 0 120! , CH3 CH2(2-(0113)Ph) HTi CECB CB2(HI3 Cl1IzC!3 CF3 CB2(2,6-Cl2Ph) H II c=cs cyz2cII3cyr2C113oi, Q-3 BB Ph Cl12CIl1 3 C112013 C)+3 Cl2(Ph ) HR” 22R31i'R5Q I II Ph CH2Cl'13CB2CB30H3C1i2(2-rPh) ) l)I Ph CM2C1(, CECR3CM, C2(2-(CH3)P h) HFI Ph C112CC112C!2(!13CI3 3CH2(2, 6- Cl2P)l) Hll Ph Cl12C!13C1112CFI3Gi l130-3 HB CB20CJI3CIi, C1130120f3C1i, CB2(!'h) tB CB20CR3CB2013012C13013C Ii2(2JPh) 11H 0120C1+(,012HB3elf2CH3c B3HM2(2-(013)Ph) Hll 01001,CH2Cl, C 12HO3 0 !3 CHI2(2,6-Cl2Ph) Flll 0120C R3C1l,CB, Cm2CH3C1'!30-3, HB I'l CH 2Cl(2H'B3Qlmouth213α2(2(mouth,)Phα2<2-<mouth,)P h) Hll Hcm2ci2ci, cm2ai2cm, G2-rph+ 'cyr2cz-rph)HCm3CM3B H CB5C112(2-rl' h) HCB3C)+3H H 0i3CB2(2-C1l'h) IIO!3 CM, il, H Cm3Ci12(2-! 1rPh) lIC1!313 B H CM3C12(2-(G3)Ph) HCil,0131i B CB 2012(2-(HCl3)Ph)- R013ell, B!!0130 1(2-(CN)Ph) lICm3C1l13H II CH3C' FI2 (2-(CF,)Ph) HCl1,C13H Helf, C1l(2- ((Kr,)Ph) H013CE311 11 Ko3 C2(2-(SC3> ph+ iCl,0f3B H C1i, Ql(2.6 -ff)21'h) HCR3C1!, H il 013C112 (2.6-(C1)2Ph) ll0113 CHI3 H B CB, G12 (2-Billy, >, z) - B013 CB3 B B 013 012 (2-7 )' HC: Iiz c113B Ti, Cf13II2 (2-tetrahydro7rane)B -Oi3 B B C113 Cl2 (2-tetrahydro7ran) Hl:H, CB3 11 II 013 Cm2 (2-the 5-needle fuyu=sure) H mouth et al, B! C13CEI (2-ynynol) 11CH3 C13 H Neck C B, (:B2 (2-Bichi) H013Cm3II Ii Cll3C1 2(Ph) +1H"B2R3B'B5Q X C1 (3HM3H I'l CM, Q-I HCH3Cl3l H C H30 -3 H013C1131'!II CB3O-6 11C 1 piece C1f3 H H CB3 Q-) HCm3Chi, H H 0130JS HCi l, CH38 Ill CHI3α2C1i2 (2-rPh) B013CP i3H R CH3CM2C B12 (2-CF.Ph) 11013CTI3) 1 ) 1 el13012CI!2 (2-(CH3)Ph) l'1 Tsukuda3CM3 H H mouth, 2 G2 (2.6-F2Ph) HCH3Cl3l H C13 CHC13CH2C total ph > H (J13CM3H H 013HM20!2 ( Ph) HCl3H3H R 013CI'12Q-4 HCl3CH, H H CH3Cl1!20-3 HCH3Cl3l( H C!'1.0120- 6 8C1(, CM, H H CM3C1(2' O-7 HCM,C) + 3) I H o( 3HM20-15 !'ICM3Cy!3H H CM2CH IICH2C1i2 (2J!'h) HCl3CH3I ( H 012C11.Cll2H12 (2-CIPh) HCO3Cl3l H 01 mouth-mouth 2 C 2 (2-(mouth 3)!'h) HOf, Cl3l H CF!201=012O H2 (2,6-Cl2F'h) HCH3Cl3l H C112CJ1.0I 2CH2 (2-CF, Ph) HCm, Low H H Kuchiraroto 002 (2-tetrahydrobilane) HCH3 CF3 H H cm2c 'yi*oi 2 C'EI2 (2- Piriufure) HCil30f3H 11 clH2C H-IQI2CB2(Ph) Hol, Cl3l H 01201=C!I20 -I HCM, CEllH, II Cll2H11.CEI20J HC H3Cl3l H 0112C8*CH2 0 -6 HCH3 CH3 H H C120(=CH2 Q-7 HCl3 C1113 H H C1C112 C11!12 Q-45 11111R2!13B' +15Q X CI(3013II HC)I2CI(, CB(CH3) cm2(2,5-C l 2ph ), HCm(, Cl311 m? Cm2CE, CB+CH3) O −3HCM3CE3II III C1’! 20CR3CR2(Ph) HE" 12B3B' +15W jl3CI(3013CB(2-(mouth,)Ph) HCH3CM3CM3013013CH2( 2,6-Cl2Ph) 1(0 3α3C)+3 σ3 口30-3 1itCjf3C1130f3CE3CH 2C!l3CH2(Phl Hα3C')+3 03cs, CH2CH3012 (2shiPh) HCi!, CH3013C1(3CB2C113C R2(2- (023)Ph) C013CI (j 0!, C113CB2O!, C11 2(2,6-Cl2Fh) IICE3CR3013C113CM2CH,Q- 3HCH30I3OH□Cm2CH130,CH3012(Ph) HCm(3 C1(3012C)12C) I3CH,C13e l12(2-rPh) C01 3CB, C1112C1112012C ,CB, CH2(2-(CH3)I'h) 11cH,0130112CR2C1i,C1113CHI3C'!!2(2,6-Cl2Ph) It013CH3C112C1i201.CH, CB, O-3[IC1i20!3CM2CM3II HC113(m C113 (+1C12CR3CFI2OR, H11CH , C112 (2-FF'h) R CR2C'!i3 CH2Cl3 +1 11 01.CH2 (2-(CB)!'h) HcB2C113CH2CH3HH013012 (2,6-Cl2 f'h) II Lolico, CH2 mouth, B 1lc1 !, Q-3PIC112C 13C)!21JI3HHCl2CH3CH2(Pb) ll0120f3C' H2Cm3E FI C112CM3CH2(2C112CHCH2CB3CB 20!, If 11 G+, 01.CB2(2-(CH,)Ph) if Mouth I, el13CII2CI, HHCm2C1, Cjl2 (2, 6-Cl2Ph) HO20301, CB3PI!!01,01.O-3H012C1l13 012CM3!I II Cm2CI1.CH2CB2(Ph) 1012Ch i, CB+CH3HE C11201,CH2CR2(2-TPh) EC1 12C H, (:B2ell, ! i II GI2CBmCH2CFI2(2- (Cjl,)Ph) lIC112c1i3 CCm2C,Ti EI CM2 C111F C112012(2,6-Cl2f'h) ll01201,C1l, (J,E B CH,C+CI120-3 1 1012CH, CB, CFI, cE13013CM, 0112(Ph) HB" +121' R' !l5CL , CB, 012elf, CH201 ,C1i, C112(2-rPh) 111 CI!, α2C112C'13 α203 口3 口2(2-(口,)i'h) Bit CH2CH30120f,C1 201,Chi, 012(2,6-Cl2Ph) HHC1C1i 012 C113CH2013CBz O-3HHCmiC11012CB3 CB+CH 3,013012(Ph) IIFl cEcm C11201,ai□o+, Of, cm2(z-rphc IIHCmiO!Cl2C1i, 012C 1!, 0! 3 CC02(2-((,)Ph ) 11m c=cyi cm2 am, cm2an3CI!, 32(2,6-Cl2t'h) B!Ic=cm 012C!I, cm, cy+30130-3 Hll Pl+ C11201 ,CH2Cl, 0f3C12(Ph) ll1f Ph 012CI !30f 2CH,Cjl, ,CB12(2-rPh) HiI Ph0120f,01 2C1i30i, 01.(2-(CI,)Ph) 11B i'b CH20 1,0i2(B3 CI, 0H2(2,6-Cl2Fh) EIB Ph C B, ELL, 012013C! 13Q -3ILL 0120CR, C1120 1,012OF, 01.OF2 (pH) HLF C120CR, 012C 1,0! C1 , mouth2ko3 α3ko2(2-(mouth,)Ph) HI 0f 20CR3012013C12C!I, Of, 012 (2,6-Cl2Fh ) +1FI C1C11zOCCH2C+13 CH2Cl3 CB3 (> -3BII I 01232c1, C+1 2CB2 (m, 0f2 (2(0' f,)! 'h 0M2(2-(C1i,)IPk+) HHII C112C! 1201,01,012C! i, (2-rPh) C+12 (2-rPb) I fE1!12!13! I' 15Q cT12(2-C1Phl IfII It 012013CE2CM3C1i, ClI2+2-BrPh) 11! I FI 0120! , O12CM3C113CB(2-(C1i,)Ph) HHH012C'113C1i201301. Of2(2-(001,)Ph) BHII C112CH3012C113CB, C1ji2(2-(Of)Ph) IIH11c11C11301C1l, CH, C1, (2-(CF,)Ph) IIH+1 C112C1i301013C1l, C 11 2(2-(CKT, ) f'h) IIHHCRCB, CR2CH3Cl13e l12(2-(SC!i,)Ph)11 HCH2Cl,C"H2C1l, (m, 01(2,6-(F)2Ph) HII II 012013CHI 2CB, 01,012( 2-6-(C1)zPh) mlB H012Of, 01.CH3012CB(2-Biraj=y) IfII HCBzC)lx cm2ci+, CH3CHz(Ph) HHI 012CH3012C113C H3QJ itHB 012013012 CI!, 01.Q-311HB C 12Chi3C112C1i301.O-6IIM B C11201, CB 12C!i, 01.O-7BHII CM2C1130f20I, C1l, 0-1s IfII B 0120i3CH20, α20.mouth 2 (2-f fh) +1FI II 0120!, 012 (m30120f, CB2 (2- CIPh) HII II 012C113CH2CH,CB2013(+2( 2-(CH,)!'h) IIHFI 01201.CB2CB5ClI20 130f2(2,6-Cl2Pb) 111I II 012C1,C1C1 i,CH2Cl3.0f2(2-T,jh ) HB H0112CII, 0 f2Q13 01201. 012 (2-f trahydro 2 run) 1rif I I CB201. 0r2013 0!201.CB, +2-, Biri9z) mII HCll2C1ll, C112Ci13CI!2ko3 α2<pH> ysB1E2II3B4B5 Ω XII)IC) 12rM3C12α3 Punishment 2α3Q-I HHHCH2Cl, CH2013CH2CH3Q-3Hli HCl2C1(3C12CB, 120. g-6Hkl HCmCm2CCR2(B3 Cll2C1i3 0-) HHHII CE2C113CB2C B, Cll2C1i30,15 1fB B CH2Cm3C:R2C11= CE2C11 no CI'!2 02(2-r Pk ) FIFIB C112r:H3042Cm33201-CM, CH2 (2-CIPh) ll11 1 CR2C"83 Mouth 203 σ20 Wing σ2 C2(2-(mouth, 1i'h) EHE C1!2CH3CB201!3 CH2 Cl, C1(2(:ll2 (2,6-Cl2f'h) IIIHH012C13 C11203αzcH window α2C112 (2-Cr3Ph) EHHCHzCHx CB2CB5 CHzCBmCHz CHz(Ph) Hll I CH2C l3(H2CF1. CH2Cl’! , CR20J ifHHCB2CR33B 'O12C113C,01<H2O-3HHHCH2CH30120!3CM2 CH*CH2o-a HHII C142C13C)I2Cm3 Cl2CH, C'H2Q-F HR)I Cm2CR3σ2α3 σ20 Electric: I! 2O-1s IIHE E FI CB, C112(2-FPh) H1! BHH01,012(2-CIPh)! iRHiI HC'lN3 mouth 2 (2-(mouth et al) ph) nM HHII CH,0f2 (2,6-Cl2Ph) HE B I I H0i3012 (2-(?3Ph) Hll HE B 0 et al CB2 (2 -7 door hydropyra '/) HHHHHC113CE2 (2-Pili ψshi) HH HHE CB, 01 (F'h) IIIHE E I CB13QJ H HII B B 013Q-3H HHPI HCB50-6 E HB FI HCIi3 Q-F H HHIII HC H30-15Fl R' to R2E3' 15Q 2 Ph) III HHB 012CB3 CH2 (2-CF, Ph) 'HB HHII CB201. ell (Z-tetrahydropiraf) HHHHI II C1!2CB3 CIi2 (2-pyricifre) Hll HHIII 0 120 et al. CB2(Ph) IIHHHE 012CIl13 0-I Hif Hl'l 1ICH2CM, O-3FfHHB HHE, CH30-6BI I B 11 HCB201. Q-711! i HII B 0120(, O JS HHH 口I, 013 CO3Cm(2-FP!z> l1m1 il CB3 013 013 CB2(2-C1!'h) BII m!CB3 C13CE, CB2(2-(口1.) Ph) HHII ON3 0i, O N3 012 (2,6-Cl2Ph) ifHB CB3 013 mouth et al. mouth (2-CF3F'b) Hlf it el, C113 mouth et al. CH2 (2-te trahydropiraf) BII II 01. CI, 01. ON2 (2-, Pili Fre) BB H Mouchira Mouchira Of, 012 (Ph) BRII C1 l, C'1i3CI30J III! ! 0! , a et al. CB3 0-3 11B 11 013 Kuchi et al. CB3 Q-618HCB, 013 CB3 Q-,7MB iI CB13 CB3 C1130-15 Hol, CEI, 012C113 Rollo et al. Kuchi 1. 0i2(2JPhl 50130f, 0 f2e11.012Chi, CB3 012(2-C1l'h) Hol, 0i3C!1.Of, ON, C1l, 01,0i2(2-(CB,)Ph) 1!013C113012CH,Chi, CIi, 01.CB2(2,6 -C121'h) !lCH3013CEC?!, C1120!, CIi, CB2(2-mouth', ph> BeE, Cm, CB2CB5.CEI, Q!, 01.CIi2(2- f trahydropiraf) HE1B2E3E' H5 OH Cl3 C13CH2Cl, CH2Cl3 CB3 CB2 (2-pyridyl) HCl (3C'B3CM2CM3012C113CH3CM2 (Pk++ 1 1013CM3CM2C1l1013C'H3CM3Q- I IC'ff303 C'142CH3CB2C'E3 Duck 0-3 HCM3C'l13C112C M3el12C113C1 ( , O-61!03 Mouth 3 02σ3C1l12C' !I3 α, Q-711CB, C13CMC13C,, c+H2CM3CM30 -15 1iCM3013C)!3CI(3CH3C'H2(2-FPh) H C'H3CR3CM3C1'13CM3C!12(2- C1Ph) HCl3C 1!3CM3CH3C!!3C!!2(2-(CB,)Phi Hol3 43 CM3CM3 ko3CR2(2,6-C1Ph) !ICM3C143013 C'H,CB3(H□(2-(73Ph) 11013C'FI ,, CH2C m3 HM3CM301.0I3CH3QJ BCli, CIf3Cm3cB3C m30-3 11CE, C)!3C13Ch!30130-6 11O!, CH3C11301,ClO3Q-F HCM3CH3C!1.C'1i3C 1i , 0-15 HCH2CH3CB2CFi, C3!2083Chi201.013CB2 (2JPh) BC1llC713CB2CM3C713CB 2CCB3elf, 01 (2-CIPh) HcH2CM3C1i2CFi 3CH□CH, CH2Cl1.CH3CB2 (2-(CB3)Ph) 110 I□C'H, CB12CB3CB2Cm 30f201301.CB2 (2,6 -Cl2Ph) !ICM2C113CH2CH3CE2C1'+3 Tsukuda 2CM3 C113012+2-Cr5Ph) HOI2 duck CM2CH3CB mouth, mouth, low (2-tetrahydropiraf) HCI+2 (:'H3C1112 CR3CH2Cl, CH2Cl3 Cff3 012 (2-piry, ;q) B012013C H2013C112C) 130203CH, Cl2(Ph) 1ICR20 !3C112CH3C11i, CCl13C! 2C1i30f, Q-L HCB2013C1l12OH3Cm2CM3CM201. CB, O-3RC82CM3el12CI! 3012cH3CB2CM3Ca! 30- 6 EC’112CM3 CR2Q13 CH2Cl113 C1C12(C’!!, Q-) HCE2C)13 C’! 12C) 13 CH2Cm3 CH 2Cl3 C1 (30-15FlEIE213R' H5OX CH2CH, C1i2C112C11σ30 (2,6-Cl2Ph) ItC E2CE3 C2C13M B CR3Q-3Hat2ot3co2c'PI3 CB , CB, cn, as2tph > HCH2C)1. (112r13CM 3C!i3C13(B2(2-r!lh) 1!Or2CM3 0f20(,C 1l, ON3 C113CH2(2-(loco)ph) 1tCBC113C H2C14,CB, (:4.013C112(2,6-C1, i'h) I IcR2(H3C12CM3(m301.0130-3E CM, 012C II3012CH3013C1i2(1'hl IIIH013Cm20f30 1201301.CEI2(2-r!'h) 11)I C11130f2C M3 C1 !2e!113 0f, Cl2(2- (Chi3)Ph) III I C1'!3012C1l, C12Cm3CII, C'12 (2,6-Cl2 Ph) IIIHCEI3 (12Qi, C112CE3CB, O-3ffB"1 i2H" E' B5OK!!112R' E' R50X HM OR 30 !2CH3(m, CB2(3-CYuph) 1Table 2 X and Y are C(R3)(11')OR5 (unless specified) l:!(3(m2C O3CO3C12(2-F!'h) III HC11i2C'l!30r2 CM, CIl!3(m□(2-C1f'b) HF!HCE2CFfko 0f 2C!!, CB, CR12( 2-BrPh) BHHCH3CN, CH20 13CE3CE2(2-+CH3)Ph) ifHII CB2Of3CM2C E30f3c'H2(2-(001,)Ph) BHHcE2CFI, CI(2 C1'f, 01.CH2(2-((:N)Phi HHHCH2CN3 01 2CR3C1l, CR2(2-((T,)Ph) ifHH(m201.Cl12C113cE, 012(2-(OIT,)Ph) B1'l l 0f2 CH,ot2or,OR3012(2-(SOl,)Ph ) HB R10i2 C1i3CB2el13C11,012 (2,6-(r)2Ph) I11!HCi20f3 elf20f, 01.012 (2-Birajhisole HI I II C112cil, CH2CN3 C1'l, Cm2(Ph) I!!1 1B2E3=B' E9 = R10 R50 B HcE, 0f2(2,6-Cyu2ph) IfI f HHB Cm3Cm2(Cm3C,Pk)! ! ! 1. If 11 FI C'H,, Cm2 (2,, tetrahydropiraf) HB RHB CFI3 C 112 (2-pyricifre) HHll 11 II 013CI'12 (Pkt) Hll HHHC1130-I H) I HI'l l'I C1i, O-31! HHIII HCm3Q-6I II 11HHB CO,Q-F H HB B III Cm3Q-15IfIf RCM, CB, CB13 C H2(2-FTh) IIB 11 013 (B3 C1l, C112(2-CyuPli) 1111 M elf, CB3 CM, CH, (2-(CM,)Ph) ifRFl 01!3CH3CH, rho(2,6-Cl2Ph) HHH013rof, CH3Cl2(2-(J3P)l) 1!B 1!C D3 CI'! 3 CB3 CB2 (2-tetrahydrobilane) III iI Of3 CB, 013 CI! (2-pyri9y) 1iFI HC113 01, CH, 012 (1'h) HB B C1 (3C) f3C1l, Q-X B11 H013elf3C1130- 31tII PI CH3Cl0.CB,Q-6EIHH01,O'+3 013 0-F RII H01,CR3 CR30-15B1013 H0i2e113 0i2CH3CH3CB2(2 -FPh) !1CH,B CB2C1,CB2Cl, C111 3CB2(2-CIPh) !ICII, II CB2Cl, 0f20i3 CH,CB(2-(01,)i'h) HCl13HC112+IN,CR2CR3C1( 3CB2(2,6-Cl2m'h) !IC113F!012C13(m2C R3CH3CB2O12C13('h) B311 B2 R3 , R4B9=R IO15Q XCM, HCH□CM3 mouth N, C11, mouth 0 (2-tetra Hydropyran) HCHI, B1 CR2CR3C112C1i3 C13C 'H2 (2-pyridinot,) Hol, EI Cm2013CIi2C1130 13CIi2(Ph) 1lci3n C112cC112cH3ot2. O-1B10131! CH2C8, CH2Cl1.013Q-3BCII3F i mouth 1. l’l, CH2Cl1.01. Q-1s II (m, EI C B2C113CH2Cl1.Of3 Q-7HCR,, HC112CR3cH 20131:'H3Q-1511012CB311 CM3C113013CO 2 (2-r!'l+) HcH2C1 (3HCB, ell, CB5 Cl2(2-C1!'h) 11C !12C!13HCyo3CII3 ko3Cn2(2- (CB,)ph) itcH2CM311 CR3Ql, CM3CR2(2, 6-Cl2Ph) HC)I2CI'13 B Cm, (koi3 cm, cC 12(2-CF3f'h) IfC112Cm3HCB3 Mouth (3C113CI I2(2-Tet7hi)'Robiran) HCR2ci,n CB3 (Proof, CB 3 CB yo (2-゛Birisifre) HCl12CB, 11 01301.CH ,012(Ph) II0!2013 I CB(, Mouth 3 (:EI3 0-1. lICR2α3H33mouth, α, Q-3 11CFI2Cl'!311 C1 11312, CB30-6 Wing 01, CM, HCB, Of3 01.O-] ] Father-in-law, CM3HC13C1l, 01.Q -15B!+11!2E3- IF' 19410B5Q HCB5Cl2 (2 ph > nCm, IIFIHC3port2 (2-C11Ph) BCF!, EI HH013CI!2 (2-(C3)Ph ) HCH3HB II CEj Cil2 (2,6-Cl2Ph) 1fC) 13 HB HCHl Cf12 (2-Pyri a little) HCl3B !!il C1113012(f'h) 1tC1, Be1l, mouth, (m3Q-11I C1l, HCB3 CIji, Cil, Q-3HCl3B α3C113Q 130-6 1f013 HC113CB13 Cil3 0-) H013H C3C11 C130-15II (:'H3B CB, Of , CH3012(2 -FPh) 11Q!3RCF,3Cm, 013012(2-C1l'h) IfCB,II Q!3C1l, CH30f2(2-(Cil,)f'h) Ifc113 11 CB3 01.CB3 012(2, 6-CB21'h) 1fC13B 013 013 CB3 C112+2- Pili9)b) IICE, HC113013CH,012+1'h) 1ICH,CB5CH3 CB5C13f)-1! ICE, C1i, 01. CH301, Q-31ICB 3 (113013013CB, Q-611CII, Cm3C! I3cR3CM, %7 HCR, CC1130f3C1i3C, Q-15B11g2 n3= n4 R94No!+5 Ω XCR3HH0i301.O-611 CM3HI3 CH3Cll3Q-7HCl13HH, duck α, OJ5 B Cli3 HHC '13 0g, C112 (2JPk+) BCli, 11 HCB50f, 0f2 (2-(lPh) B013 II HC1333012 (2-(CB3)Ph) HCl3B HCH301, CB12 (2,6-Cl 2Ph) 11CR, HII C'H, C1i, CI (2-viridi Jlz) ICE3m!!!C113C3l,Of2(Ph) !IC1i, B1 B Oi, 0113013 0-I FlcH,B H012CB30f3Q- 3!fOf3If B 01201.C1,O-6Be1l, H 11Cll 2C1l, 01.Q-fu HC) iyu ii II C120f, 0130 -15 11(:! , C112(2-(elf3)lP h) IICM3HH01C1l, Oi3Cm!2(2,6-Cl2Ph) 110311HCm20303 C2(2-C3Pfi) HB' E2!!3 -E' B19=E10E5Q XChi, IN HCHI201301 3C II2 (1'h ) EICI (311013HCl13Q-I HC) 1.R CM31i α, Q-3HC) B311 C1i3mI CHI, Q-61 fCM3HCB3!i CH3Q-7E C1'13HC83E 430-15 H-CH3I C) 138 CI (3C H2 (2JPh ) IIICM3RCH3I CM3C1'!2(2-CIPh) FICM3RC1(31'i C13CM2(2C13C,1Ph) HC l3i1 C113HCi, C'1i2(2,6-C121'h) BCH 3HCB3 III Ca113 0 12 (2-bilicifre) HCl3HC8 3HCB3012 (Ph) B!11E2!13 Discharge 4 B9,110 HI5 Ω 3Hm (3III CB2 (m3B 0203 Mouth 2 (2-FPh) ”C B3 If CH2Cl3! ! Of2CM, CII2 (2-CIPh) EIC143FI CH2Cll3B 012C1,Q! 2(2-(Of,)Ph) HCO3HC112C1i3 E 0112Cm, Cl12(2,6- Cl2Ph) HCl3HCH2Cl1131!0(2CE13012+2-C F3m'h) HCH,H01,013C121'h, CE, CH2(2- f tiger Hydropyran) mCm3 11 (1"H2C1l, CB(2CR, Cl13 0f2 (2-pyri-sifre) HCH31ClI20!3CIi2C R, C113C12 (Phl HC3Hα2α3 口2C113α30-I B C113!I C112C:B3.CH 2Cl30130-3 RCl(3 )I CE2C1l13Cm2CR3Cl, Q-611CH311CH2Cl3 CH2Cll3 C130-7HCl3i1 0!1. (i2Cm3CH3 Q-458E112R3-R' B9-B10B5Q !2(2-F7Ph) H012el13HCI(3H M3CH301(2-CIPh) HCOCM31 !CH, Cfl, C 1,3012 (2-(01,) Ph) H01201311CH3013013 012 (2,6-C121'h) HCi12CH3HCHI3013 Mouth 3 Mouth 2 (Ph) IICE, CH31'I C'H3CM3CH3Q-I H01 2CO3HCM3C13CM30- 3 HCH, CTI, HC) I3CH301 3Q-6110S:H3HCM3Cm3 口3Q-7B(m2el13II C H3Cl, CIi, Q-15IICB3HHB cH3Q, -I B α, 11RII α3Q-3H 013!I!11 E 013Q- 61fCR3HHH013Q-7C 0i3HB if Of, OJS HCl, HH11CII, aI2(2-rl'h) ll013HB HCH3012(2-CIPh) HCl3H It HC1f30f2(2-(0113)Ph) ROf, II II H C113012(2,6 -Cyu 2F' h) 101, RHH0130f2(2 -CF3m'h) Bol, il B!i(m3012(Ph) BCl 311 Chi30130!3QJ llICB51!CB, 013CR3 QJ IIICM, B CH3CH3elf, Q-6llCm 3 RCH3 CHI, CB13 0-F HC ) M3CC113CHI3CE3QJ5 H R” R2E3w=E' R9-110R50XC) 13HCM3Cm3. (m3C112(Ph) HCl1.CH,CB5Cll3elf, Q-I HCl3i1.(H,01,CR,O-3)ICH3CM3CB3011.Cl130-6 BCH301,CE3 C1i, 011.Q-7Bcs3o i3cs, 013C1130 -15HC'H3C13CH3CH ,01,CB1 2(2-rPkt) EC″Ti3 CH3(:B33 C'S3 C3C2( 2-CIPh) 11C113CHI3Of301.0!, 012(2-( CII,)f'h) HCIH3CM3CII3C1,Of, Cl2(2 ,6 -Cl2Ph) B013CR3C3(3013C1i301(Ph) HC l3i1 B 013CB, Q-11tC83M B CB501.O-3 110113B H01,C1130-61fCM3 HI C1,Oi, O -7Bol, 11 H CHI301. OJS Bα3it B C113mouth 3 C2 (2-juice h) gCm, HHoI3oi, (m, (2-C1i'h) Bol, !i I Of, ri, 012 (2-(ko3)i'h) BC H ,If I 0f3Cil, CH2(2,6-Cl2Ph) IIcH,I I E C113Ci13ell+2(2-CT3Ph) HEI B2 .3 .B4 .9.E:10 BS Q instrument C131't HCM, C13C!!2(Ph ) HCl131!B CH2Cl30130-1HcH,HHCM , CM3C13Q-3HCl13B HCB2CH30 (3Q-6HCl3H) I 012CM3CE30-7 HCM3m'l ) I C1112CH3CH 30J5 HCl3HHci12 CH3CH3,C1!2(2-FPh)! I CH3HB C1112CH,C1i3HM2(2-C113CHCl3HHC 12CM3CM3012(2-(013Cl2CHOf3HRC112CH,CB3022(2,6-Cl2Ph) HC1!3 1!II Of2013 CB, CH2(1' h) !ICH3HCB3B Ca1130-I M01 3If Chi, II 01.Q-3111I3Hm1l13HOf, O -611013M 013B 013Q-7H α3II CH2OC113QJ5 HCl3i1 C1i, 5CH1012 (2-n'h) HCl3HCM, B CH3012(2-CIPh) BC l, ! 013if 0f3012(2-(cE,)i 'h) Ifell, II Of, B1 01.012(2,6-Cl2Ph) IfCm3H C113![013012(!'h) !!Table 3 HII CH2013cE2C1l13 CH3C112(Phl B!11E 2B3.1' B9-E10B5Q XH) I CM2CH3C"H2C13C 'H3O-611HHCH2CH2012C13C130-F HHH%930 20.CB3045 HII II 012C13C112Cii3C!12 0H,Q12+2-FPh) HIII FI CB2σ3C12Ca 13el 12α, Cl2(2,6-Cl2Ph) HHH,CH3CN,C12CM3 CH2C'j13CM2(! 'h) HHRCM2C13CM2CM3CR2e l13QJ 11B FI CM2Cm301C01011, CD30-3 IIHHC112 Punishment, CB2CB5 α2Go3g-5 HHlt α2130α3 Mouth 2α, O-71B H':B2CM, Cl2Chi3c 112el1 30J5 1HHC112C[l3C1!2C:H,012CH,O!2C12 ( 2-FPh) HHRCB2Cl1.CB2CB5.Ca12CEmCj i2C112(2-CIPh) IIM RCl2C'R3C112C113C 112Ci1.Cl2C12(2-(ell,)Ph) Ifd l!Cl2 CF,, O12Cm, 01 2C!lm0I2Q12 (2,6-Cl2Ph) i lHB c1+201.CH20130f2C21,QJ2 C112(Ph ) HII !i CaI2C!+3 CBzCBs 0f201 proverb 012 Q J HII B1 C1l, CB134m2C1i, CH20i=eB2Q-3 III jl CB2CD3CBzCH3Cl2C1wCBz Q-671H 11012ko3 Gsu13 α20L, CH20- 7IIBB Mouth 2C1!30 1233 α20-:112Q-45H11B213=R' E9=1" 15 Q, i) IIHB H11013Cm'! 2(2,6-Cl2Ph) Rif HH H013C12(f'h) HH11H11CB50J H BIERB 0X3Q-3If! 'l HHB 01. QJ H HIM H01,0-F H HRHHC1130-151f )I HC) (,CF!3 mouth, α2(2-FPh) III FI Ca 13cR3013CR2(2-CIPb) HH)I Cll3C'! I, Cl130!2 (2-(01,)Fh) HHB 01.01.013012 (2,6-Cl2Ph) HIII II Cm3CE3013 02(i’h) IIHH013CF! 30f3QJ H E B C1130f3CH3Q-3B11 RCM3013CI, O-61!11 11 0!3 CH30130-F EB HCD, cB3013QJ S! IC! ! 3HCH12(m3C112(口3 口2(2-rih)B013!i CB2C1'13CI203 口, 口2(2,6-Cl2Ph)II C)I31f(II2C3i3C112C!13CH,CH2(2-("F3 1'h ) l'1B" 12g'-R' B19-E10B50 -CIPh) IIH013c11 mouth, 0120f, 01.Cm2(2-((II,)Ph) III Of, CH 2013,0f201.01.C112(2,6-Cl2Ph) l111 α3 α201 mouth 203 mouth, CB12(Ph) HIII C13C1120 1301201,01, O-11!i!CD3 012CR3012CHI3 C1130-ko H!l"!!213-B' R9-R10E5Q 3 mouths, 0- 15 EIH II CC311CM, CB2 (24I'h) 11Rif CM3II Cm, CB12 (2-CIPh) IIHB Of, HC113C112 (2-( C1l,)Ph) HII HC113BCh13C!12 (2,6-C12!'h) IIHII CB3El 01.CR2(Ph) HHHCH,!!CE3QJ H Bli CM3H (m30-3 M llFI CE, B CH130-6HHHCB, EI C8, O-) R RHCC311C113QJ5 1i CO, RI'l CH3CN, C2 (2JPh) ”CB511 HCH301 ,CHyo(2-CIPh) HCl3HIII Cm3CR3Cm3CR301 2(2-(CIC”C311H013CH3ell!2(2,6-Cl2Ph) 1t013B 11 0130f, HII2(2-(T,Ph) HCl3H II 01.CH301 2 (Ph) EICH, EI H0i301,0-I HCH,HH01,CH30J H Cll3HB CR3CH30-6B Cil, B II C113CB3 Q-7HCl3HEI CH3CN, QJ 5 Hl1112R3-R' R9-R10E5Q XCM3mi FIB Cll3CIl! 2(Ph) 11CB3HHHCll30-I IIICH, HHH(:E3Q-3H C)13HHII CE3Q-6H 013B HRC1113Q-7H Cl3Hii B CH30-15! ! 01, HCM3C13Cm3CI! 2 (2JPh) 1fCH3HC03C113CFf3C1i2(2-CIPh) 11C13HC13CM3CH3CH2(2-(CM3C13C1lC13I f C13CH3CC13CH3C,6-Cl2Pkt>!IC1i3HC1 13013C13CB 2(f'h) HCl3H (m3C1301, O-4 days C13H, C) i3Q130130-3 HCR, Ho13011. Cm3Q J BOi3 !l0i3 013 CB3 Q-fu H01311cm, 0 1.0+3QJ5 HRl, 2!3,4 B9.10 .5 Ω.

HHCH2n3C’! l2C13CO3012 (2-FPh) HB E CH 2CH3CB2CD3 CB3 012 (2-C Yu I'h) H11R2! ! 3 -B’ R9=R10R50KB ii C112C113CH2C″H3CB 302 (2,6-(F)2Ph) IfiIHα2α, eH2Cm! 3C1l, Mouth 2 (Ph) HRRCR2α3Ch12C11301, QJ IfII H Qi2C1i30!2CE! , 0130-3 IIIf ii CH3CN, Q 120i30. O-6ifHHCll2CI3 0120!3 01. O- Hll If 012CB3012 (m301. 0-15 11H110 12CB3 01!2CH3CC112(, C112(2-FPh) HII B C1C112e, CM2Cm3Cm2 (H, 012 (24F!n) IIM B CB2013012CH3Cm2CO3,012(2-(Of,)!’h ) HI HCM20f, 012CHI3012CE13C112 (2,6-C l2Ph) EIHEI CE12C1'13C1i2Cl, C12Cm30i 2 (Ph) EIHB CH1201, 0f2C1i3012 (:’R3QJ HHEI 012CB3012CE130f20'+30-3 H11R2E3 -E’　B9-R10E5Q　XHHC)I2CH3CH2CM3CH2CH3 Q-6Hll HC12C1C12C13CH2013CE2CHB HCF+ 2C’H3O12CTC3C1i2C’B3Q-15HB HCH2CH301 20H, CH201, CH2012 (2JF'h) HB HCH201, Cm Cm2C012CH,Of2　C112(2-CIPh)　IfII　ii　C B2CB5C112CH3CH2(%C1121m'E2(2-(HII3)! 'h) Bit II e112C7f30I2CR307201=12el1 2 (2,6-Cl2Ph) Bit H1m’H2σ3 α203 Ko20 Snow α 2012+Phl EBill Mouth 2α3 α233020 Tomiguchi 2 QJ II B B (J!2C713CI’f2Cii3QIzC11h011z Q-3 1t1111 σ2C'1f3CII2α3020 Sea Q-5Flm vI cm2C1 (3C112an3 Q!2CBgCHz O-7Hl!! C1 12CR3CHZCI! 3CHI2CF! *CH2QJ5 HHH1! II Cll3CB□<2-toI3>ns+ m111111 EI C3012 ( 2-6-C1zPhl IIHH11HOf3 012 (2-pyridyl) HB HHHCH, CE2 (Ph) EIHH1! H0f3QJ H II HB HOf, Q-3il lol ii! ! m 0f30-6 Hl1 11 HHOi, Q-7! I B! i! i H01, QJ5 II Breath” B2E3-B’ R9-R1015Q Ill” 12113WE’ R 94” 315Q XCm3If HHCM, C112 (1’h) IICB , B Ti II CR30J ICm3HHEl 01. O-3H (B3HH1! CB3Q-611 CH, H111C130-) I Cm3HM 11 (1”H3QJ5’11CE3HHII Of, 012 (2,4-ff)2Ph) IICIH3HHHel! , (:[R2(2,5 -(F)2Ph) IICM, HI H013Cl12 (2-F, 6-C1P h) Bol! i HI c112CH3012 (2-FPh) lIC11 311HHCH201, C1+, (2-CIPh) 1fcE3B! tH0 12CB, C112 (2-(di,)Ph)! ICIJi, Hl’l HC m2C13(II2(2,6-Cl2Ph)! 10131m! II Cl2 CH3012 (deh) aCO3H! (R1012CI, O-I NCM, H lt　II　0f201. OJ H013118H0120130-6Ill CH, II If HCB2ell, O-7ICM3H111012C11 30-155013B HHoI201301. (2,6-ff+21'h) IICR3II HI 012QIsOI2 Cl2 (2-FPh) BC1! 3II HB 0f2018012012 (2-Ql’h)! IC1l-s II　HHCMI2CHmCII2(Hz(2-(CBx)Ph)　Ti013 HRII 0I2CR1mO’12 ai2tz, 5-C1zPh) ll3 11B2. B3 discharge 4R9=B10B5 Ω Xxl R2E 3-x4 door,! ! xo Bs Q vessel 03HO □ mouth, 0112C113 mouth, Q-151101 , H012CI13C! l2CB30f, CB2(2,6-ff)2Ph) 11CH201, HO12CB5CM2O1, CH3012 (2-rPh) I f012CB3B 012CB3elf2C’H, CH3012(2-(:IP h) lIC1!2CM31+ CR2013012013CI, 0i2(2 -(013)Pb)! ICi! 2013[1012CM30120+3C11 3012 (2,6-C121'h) R101□01. 11 CB2Cl, 0 12 (II3CB, 0i2 (1’b) ICR12CH, B C1□Of, C 112CH30f, QJ HC1!2CH3HCl2CH, Cl12C130 1,Q-3llCR2Cm,RC112e113Ch12C1,Cm3%6　H CH1CH213, R4, x9. Elo is Ω XCM3CH, CH201 , 口2go303 口2(Ph) HC83C1!3CO2C’H3CI! 243 CM30-1 11it CM3CH2O13C'Fi2C1! ,0130-3 Hll CB3 (B20130i2C2i, 0130J HHC1!, (m 2CB3 C112CR, CH130-7! ! CH, C1r2CH, CH20 f3CR1QJ5 IICH3HC113! I CH30f2 (2-rPh) n013B Cil, HOf, Cm2 (2-CIPh) BC) I3i1 m1l13B, OII, 012 (2-(CB3)Ph) IICB, HC m3HC111,012 (2,6-Cl2F’tll) HCl3I 0i3H Cl13C112 (t’h) HCii3HCm3HCll3 de ■ cE3 H(:113 H(:II3 0-3 H mouth, Hα3RCB50-6 11 CH, I CE, It CO3Q-7HCl1I, El CB51f CB 50-15 Hclf3HC13H0f30!2 (2,6-(F)2F'h) ! ICB, 111B CB, 1m’ll3QJ B03 PI FI CH 3 mouths 3Q-) HE1!12B3=E’ B9. E10E5Q X013HB CM, CH30-6H 013! II RCH3Cm3Q-7n013B HC1113C113QJ5 HCHI, HM 0! , 0i3012(2-rF'bl HOf, B1 HC1,013CH2 (2-CIPh) ll013HHCl3CB, , 0f2(2-(Cli,)!'h)! ! 011311 HCH3CCH3C1 13C,6-Cl2Ph) lICm3 Hif CR3QJ3 Cli2(2 - Pirisif l/II FICll, HH013CE3CM2 (1'h) ll IC! ! 3HE CH3Cl□ QJ H duck HBCB3CB, O-3H Cl3IB CB5013Q-6H CB, Hll QJ3 Cll3 Q-7HCl3IB CR3C113QJ 5 Hol, HHC112ml, CH3Cl□(2,6-(F)2Ph) RCfi, HFI C1i, Cli, 0130r2 (2-r!’h) HC l3I II 012C'H3CH3Ci12 (2-CIPh) HcFi3R II (m, 01. CM, Cl12 (2-(CB, +!’h) HCl3I B 012CH3013,0f2 (2,6-Cl2Ph) HCl3IB H 012C1l13CmO12C1113C, Ph) HO (3EI FI CH 2013all, 0N2(2-7)7 hydrobilane) HCl13 11 B C112C113013012 (2-Biri Ufuret) 8C1l13 HB 0 12CB3 CB3 012 (Ph) HC:El 3' II II C1 12(:III3’:’!” 3 Q-1’ mouth HH02go3013Q-3 III013 EI if 0120f3 013 Q-61CR, H1101 12C’f13 0i3 Q-) HCm (3EI II CH2013Cm3 0-15 HBI B2 m344 R9, 110x5 0 3 Table 4 x　*　C(R’)(R’+0R5 E112 13 B4 is Ω 11 HCH, C1 (201, C112C113CE2 (2J!’h) H110 4,42CM3CM2C Town CR2 (2-CIPhJif B CH3012C H3CH2Cj13C12(2-BrPb)HHCBCB5CH2C1f3CC 3C2(2-(α,)IPh)HHCH,CB2 CM3CB2 CH13Cl i2(22-(OCEko)IPhlHEI CH3(:’H20!3CB□01 ．． CH2(2-(01)Ph)H110! , CB2 (koi, CEI2 CH , Cl2(2-(Cr3)Ph)HII CR3CR201301, C13σ (2-(OCT,)Ph)HHCR3CH2CII,Cl2CB,01□(2- (5 mouths, +Ph) II HCH, cR201301□CB, 012 (2,6-( F) 2! 'h) HIII Ol, 012 0130!2 CH3CH2 (Z, 6 -(C1)2m'k)) II Kuchi et al. Cil2c"B501□ Kuchi et al. 42 (2- pitidinyl)! i RC’R3 Punishment 203 countries 203α2 (Ph) I11 I12 13 I14 15 Q, 1 312 R3,4,5Ω H11HHC03c11□ (2JPh) H11HII 013C112+2-C IPh) II B HH013CO2(2-(C113)Ph)HHHHC11 3CH2(2,6-Cl2Ph)II HHHC1!3 01□+2-Bilisi Fre) HHHM CR30JB (Ph) HHHHCR30J B ii HB CB3 0-3 RH1! If C13Q-6 1! HII HCH30-F- M　HHRCH30-15 It　H01,Of,　C1l,CI’! 2(2-rPh)l HCM3CHI 3C1l, 012<2-CIF'h)B H013cR3C113CRyo12- (CI!,)Ph)II　II　C’! 113 CI! 3 C113CH2 (2 , 6-CB2Ph) It if Cj13CB301. Cl2(Pb)B R Cl3Ph, 0130-4 1! Xi C13C113 (:B3 0-’11 II clH3C:II3 C:B3 Q-6HII Of, C13CI, 0-1B B 01. 0 1. C1130J5oI3CHz CH2CH13CBzC1]3 CH3C H12(2-Rh>Cl130!301201.(E1201.CH1Ql □(2-CIPh)01, CB, Chi2ell, C11120f, 01. C. m2(2-(3,)i'h)01, 01.　0i2elf, 012C13cH , Oi, (2,6-Cl2Ph)CB3C13012CH301□05. CB , CI+□+2-CF5Ph)B1R2E3I14!15 Ω I11 x2 B3 R4is Ω CH3)I CH2CH3CR2CH3CR30-3013II 32CB30 f2CH3 port 3Q-6CB3 I CH2CH3, CB□C1130130-7 0-7C0f2CH3C1!2CH3CR3Q-XSCIi2CB, B CB1 2013C112C’1f30! ,0f2(2-r!’h)CH2CH3! I C112CM3CH2013C112C[B2 (+ to 2-C1!’) Cm2C1 31i CBl2CH30i2C1i3C1!3C)I2(2-(CB3)I' h) C12cB, I'I Cl0CF, 0i20130f3C12 (2,6-C 12P6-Cl2Ph)CCH2CM3CM2CB5013C1i2(Ph)C 112C113HC11201, 012C1130130-1012CB, II CH201, Cl02CF, 3Cfi30-3CH2Cl, If CH2CH 3C! l2CEI, α, Q-6CI! 2C13HCf12C) 13 01201 3 013 Q-7Ci12C'113HC112CH3C12C1i, 330 -45 Table 5 X　m　C(R’)(R’)O115 p, 1! 12! 13. ! +4! 19. ! 110 B5.

! ! HCH2CM3C712C'R, Mouth, CEI2(2-FPh)R11CB 2CD, CB2C113C1(, CB2(2-C1l'h)HHCI(2CR3 CH2C1113CH!3012(2-BrPh)11 II C1Cl2CC B2CD, 013 117 2(2-(Cff! , ) Ph) III HCl2C E3CB country 303 mouth 2 (2-(屏、)!'h) B B C1(20, C1( 203 mouth 3 mouth 2 (2-(α)pb+B III Cl2ell, Cl112C H, CM3O12( 2-(CF3)Ph)!111 mouth 203 mouth 2 mouth, σ, 0(2-(around,)Ph)1!HCM2O1,01201,013C12(2-(SCE,)Ph)II II !”E2CI!30 (2CB, Cl13C H , O12CM3C1'13 0-311 8 0120H3C7(, CM3013Q-6) I B c+H2 CM3CR2CR3C"H3O-7E if 0(2013口213 α3O- 15II 11 elf2Qi3 CH, CI(, CM2CR3CB2(2- F Ph) E H Loli mW3CR2CE3 Port 2 Port 3 Port 2 (2-CIPh) 1!H012α3CH□α30(H3C112(2-(C3)Ph)1(HCH2 013CH2O13012CH3C'12(2,6-Cl2Ph)II HOf 2CH3C120i3 0!2C)B3 CB12(2 -Pilicifre) II II I CH2CH3Cl12CH,012cF13CD2(Ph)E HCM2C E3CE2CM3CH2C1430-1B HC112013C1!2CH30 12CH,Q-3!I B Cll2CB3CH2CR3012CIi3Q-6 !!CB2C11, CB2C13cm2oiLcz2ci2 (z-rph >II II 012CH312α, C1112CB=+12 mouth 2(2-CI Ph)E H012CH3CR2013CB2CB-=012012(2-(0 11,)l'h)FI HCH2CH3CBzCH3CH2CBmCHz CE I2(2-6-C12!'h)11 11 Q!20i, 0120f3 Cyo 2C Yo Kasumi Oi2 Chm(2-pyridyl)B FI Cm2013 Cl32 ON3 0i2CH,C112CB2(Ph)II II CB2013C11 2CB3012C1mCE2 ox! 1 II 012013 012013 CB201.012 0-3II B 012CHI3el121:B, CB 2CD contribution: H2O-6II B 0112CH3012CB, 0i2CEgCE 20-71! H012CH3Cm12013 0i2CE, 0!2 0-15 EI B2 B3-B4 r, 9=R10R5Qll 8 HHCH3Qi2( 2-rPh)HHHIII Q+3C'R(2-CIPh)HE HHCM3 O12(2-(CH,)Ph)I PI B II Q! 3CI'! 2(2,6-(12Ph))1 11 HE CEI3 012(2-pyridyl)EBll III 口3C12(1’k)H11FI HC113Q-1 HHHHCE3Q-3 1’! HHIII CEI3 0-6 Hi (HB CH1i30-7 11 HHH013Q-15 11II Of, C113CH3CB2(2-1'Ph)HB CH3CM3 013012(2-C1Ph)B 11 CB2C113CB, 012(2-( 013 ) Ph) HE Cl, C1301, CH2 (2,6 -CL2PH) 11 HCM3C1!, 013012 (PH) HBCI! CL13ch, 0 -15 CB3II Of2C11,012CH!, (11,Cl2(2-n'h)oi, ii 01CH3Cl!201.CEI,ai2tz-czph>CH,iI Of2013C120!3CH, (FI2(2-(01,)I' h) C 11, H012c11.Cm2C1130+3 0H2 (2,6-CX2t' h) C1!, RC120i3 012CB3 0f, 012 (2-CF,!'h) E1R2E3=R4E9=+!!10E5 Ω013HCl12CE3C E, CM3C j13CM2(!' h) cH3110i2CB3CM2C13 Punishment 3 Q-1CE3R012m1l13 (R201, CH2O-3CM31!CH2 Cl'13C'J'12α3C'H3O-60f3HcE2C!l3C12CI I3C1i30-7013H0112HFB3CECm3 CM30-45CH 201Cm3CC1f3C'H3CH3Cii2(2-rPh)C)12C11 3H0130130(3C7i2(2 -CIPh)0!2CM,)IOf, C)13CTi,CB2(2-(CH3)Ph)C)I2CH3H013CH3 CB3 口2(2,6-C1zPh)012C113HCH2CH301,01 2(2-CF3F'h)CB2CD, W C1!, (C3013CB2 (2-ftrahuman b bilan) C801,11 33 0T3 CH3Cl2 (2-ftrahuman b bilan) Rishifre) 0101. HCH3CM3C113cH2(Ph)CB2CD, I(C11I, CR3CR30JCI20!, II 0f3CE30f30- 3CB20138 cB3CB3013Q-6CH2CH,B CB3 Q10 013 0-7C!1201.B CH,01, CH!30J5 breath 1.2 B544.9-B10.5 Ω!11 12 B3.B4 B9.IIlo 5Q013el13C)! 3Cm3C13C1!2(2-FPhl(1"H, CB3 CM, CB3 C1,012(2-CIPh)01, CIH,CF 31'hm3CH2(2-(0!3)Ph)CM, 013CO3CB, ell, 012( 2,6-C16-C12Pkl) c53013C'13C13Cj1 2(Ph)04, HHC13C1130-1 CB, 11 II CHI, CB30-3Cm3H, 11CB, 0130- 6 CB3B HCF31'h, g-t Of3II HCI , 0130JS CR, 11RC1l , Cll3C!12(2-Fl'h)01,H11013 C13012(2-C1i'h)C1l, HB CHI, 01.012(2-(CF31'h)01,HHCH,03,CB2(2,6- Cl2Ph) 01 3It II 01.Cll3C!12 (2-Biri-Fure) Cm, II 11 Of, CHI, elf2(Ph) mouth, B II C11201, C13Q -101, HHC112C!I, C1130-301, II I Cl201 .CII, 0-601, B HCl12CH3C1l, 0-7CIH,H H0120f, 01.0-15C1l, II Cl201.0+, 0 12 (2-ffb), if 11 Lolico, 01.012 (2-CIPh) ell , if H012013c1!1mouth2(2-(CB,)I'h)CB3!I HCm2cFi3(I(3012(2,6-Cl2Ph)CB,!!H( J2Cg3013Of(2-CF31'h)El B2 B3 -B4 B9.nlo R5ΩCI(3HHO12CM3CHI3C112(Pk+>CI(3 11CB3)I C11130JC1(3H Duck II I:1130-3013 B 013M 0i30-6 013 HCH3II C1130-7C1(, HC113E 0130-15 C1(3HCH2X C11C113012(2-rPh)CCH3I C1( 3CM2(2-CIPh)CI, H013HCi3C1i2(2-(C'!I,)Ph)C13HC H3HCm3 CH2(2,6 -C12Ph )013 HCl13 HCB3 C1 (2-pyri ψshi) CI, Hc'113HOi, 012 (1'kl) Table 6 Z, C1113)tR') Oil5x1!13,14 B9410 B5 ΩII CM2C113CH2C1113CM3 C12(2-JPk)B Ca 12CM3 012CHI3 CH,012(2-CIPh)HCH2Cl3C 112013C13012(2-1rPh)B C1i2C112C1i3C1 2C,Cll2(2-(Of,)!'h)HCH2Cl, C1112C1i, C1i, (B2 (2-(OCH3)Th) B CH2Cl1012C1!3 01.0i2 (2-(Of)Ph)HCB201.CB2Cm30f, mouth 2 (2-(CF33Pk)H01201,0f201.Chi, elf, (2-((R7,)I'h)M 012013el12C1l, CHI3012(2-(5013)pH)II elf2Chi30i20f, CI, CHI2 (2,6-ff)2Ph)HC1120130f2CH3CHI30+2(2,6-(C1)2Ph)11 012CH,012CH,01,Of2(2-Billy) -;/A/) H0I2cB3 Ca+201. Of3 0!2 (2-Tetra Human Taviran) if CCm2(,012013CM3Cm2(Ph)!11B 3-B4B9・R10E5Q II CM2CH3CH□CM3CH3Q-1B CM2CH3CM2CM3C 'H3Q-3HCH2CH301201301 30-6HCH2CH3C112 C! (301130-7II C1Cl2C Loli J3 α3Q-15H0II2 CB, CC112C113(,CB13012(2-rPh)HCB2C1i 3CM2CB2C113C,0!2(2-CIPh)B CR2C113CM2 CH30CR2C113C!(2-(CH3)Ph)RC02CI(3C) *3ci2ca3 C2 (2,6-Cl2PhlHCM2CF+30'12C ) 13CB2CH3CE2 (2-CT3Ph)HC12CH3Cl2C)!, 0 12013 CB2 (2-tetrahydrobilane) II CH2CH3CDCm 3 012C113012 (2-Bilicifre)!!012C13C12CH3 cCH2C7l, Cl2(Ph) a cm2cH3CR2σ30112CO3Q JB 012CM3CE2CM3C!i, 0130-3HC02C'l 'f3C R,CI'13C12CR3Q-6B CB2 CE 3 CH2CB3 CF ixCM3 Q-7HCE2σ3C:E2 Go30-30-15!I CEI2 C'H3CH□CH,CD2CE,C12CH3(2-rPh)B Ca112 CI(3 CD2CE, 0i20Proverb 0!2 (B2(2-(lPh)El 01 2C)13CM2013HE201=CH2012(2-(CB3)Pk+)B 012013CB2C113012Ci1*0I2012(2,6-Cl2P h)B CH2Cl, Cm1mouth3mouth201 Ko2CH2 (2-α, Pk) B 0120 et al. CB 2C:B 3 O12CHe1 Low Low (2-tetrahydro Robilan) EI C112Q13 CB2CB5 cX1201. O12C1!2+2-Piri-Fure)'Bc! l2CIII3C112CR302G+*GIcm2cph>H012013C12C'! ! 3CH20i=012QJHCR 2C11l, CC112C1l13elf20ko, Q-3H032013C1 1zCE3CH2CI-10120-6B 012CFI3 C12C! , 0 120imOI2 0-7Hel12CH3CM2C13C11201*0i2 QJs! 11. 3=Ra l19-. 10. 5 ΩHHHC113C1(2 (2-FPhlHHHCm C-B2(2-CIPh)HHHCM3C1(2(2-(013)Ph)EI III 111 013C)+2(2,6-Cl2Ph)E H11CB, 022(2-(J , Ph)B HHCl113CR2 (2-tetrahydrobilane)HHHCB3 012 (2-pyridyl)HH)l CH,CB2(Ph) ilR!(CH3QJ HHHC'H3Q-3 HHHCii, Q-6 HHHCB3 Q-7 HHH0130-1s 11 CB3 C)+3 Cl13 C')+2(24Ph)HC1l, CH3CB, CB2(2-CIPh)IIIcl(30!3 mouth 1.C1l(2-(CB3)I'h)E C'83 C1(3CM, mouth !, (2,6-Cl 2Ph)HCH3CH3CH301 (2-σ, l'h)EI CB3 CH3 CB, C112C!7) Rahi)"o bilan) Ii CH3C113CH3CH 2 (2-biap, 'y1.) II CB3 CH30113Cd2(!'h)H CH3CB3 CH3QJ HCB, Cii3 口!, O-3 !!mouth CH3C1130-6 H 口ら 口ら CB, Q-7 !I 01.CD3CE, 0J5 Of, C112CR, C212CO, CH3Cl' 12(2-rPh)CB, 0 11.CB3 CM2O1,013CH2[2-CIPh)CH,CH,Cll3 C112C!, CM, CB, (2-(CTi3)f'h)013 C1 +2+2.Cm2C113fl'H , CB, (2,6-C1Ph)013 CH2Cl, 012CH3CH,CB2 (2-CF31'h)nl E3=R 4B9.Exo Es ΩC113C1'12cFi3Cm2CM3CR3tT H2[Ph)cs, o+2co3CH□3 ports, Q-1C M3C112CH, CD2CE, C03Q-3C'H3C+32C1i3C'H2α3CM3Q-6 c'(3C'! (2°! 3 °″2CH3CH3Q-7CB3CH2Ω3CH2 Dish, α3O-15C12CH3CH3C13CR3C1l!2+2-n'h)C 12CH3C'!(3σ3CH3C2(2-CIPh)Of2CH3CH3CM 3CM3(H2(2-(CB3)Ph)CM2C 13CH, CM3CM3CB2 (2,6-C121 'h) CH2C1!3 CH3CB+3 CB+3 CH2 (2-pyriditare) α2α, α, 0.mouth 30 (ph) 012CH3Cm3 CI13CIl, 0-10i201.013CB, CH2O-3cE2CB, CI'l, (m, mouth, 0-6CR2CD , CB, mouth, α3Q-7 012CH3Cil, (m3CB3QJ5CM3HHCH2O-1 !311 HC1,C)-3 CB, HH01,0-6 01,Hyo ax3 o-7 CIi3B HCH,Q-45 013I+ 11 CH,0i2(2 -rPh) CII3II!!CH,C H2(2-C1l'kt)C1l, HIII 口, C2(2-(口、)Ph) dan1E3=E4R9=!!10R5Ω CM3 HHCH3CTi2(2-Pili'kt L/) C'H3HHC)13CH2f Ph) cm3CM3CM3CH3Q-1 CH3(+3 CB3 C)+3 0-30i3CH3CH3CH30-6 CTi3 03 C'''3 ''3 0-7CR30130f3CH,Q-15 CB, CH3C13CM3C TCH3C13C+C'B3CH3C1(30+ 3Cm2(2-CIPh )C1+3CM3CH3C13C2(2-(C'H3-Ph)C')+3CM, C)13CI(3C7(2(2,6-C121'hl CH3CH3CH3C)+3C)12(2-IJ3Ph)C)13C)+3CM 3CI4301. (2-tetrahydrobilane) CI'! 3 CH3013CR, (B2 (2-pyri separation) CB+3 CB3 013 C'H3CH2(Ph)CB, HCH3CH3Q-1 CH3HCB3 CH3Q-3 CM3 HCH,013Q-6 CH3)I CH3CH3Q-7 CB3 II CH3C1 ( 30-15CD3 B CI'!3 013 C1 12(2-FPh)CB13 H013CH3CB2(2-Ca112CI, HC83CE, 01.(2-(Cii3)Ph)CB3 HCB3 01.012(2,6-C)2!'hlCH3II CTi3 0 !, 012 (2-mouth', Ph) CH311CH3CM, 01C2-tetrahydropyrano) 01 3 E CH3CB3 012 (2-Bili Shirere) ai3 1 0!, C1 3012 (Ph) CB3 B C12CH3CB3 0JCH, FIC1 town, C m3 CR3Q-3C'FI, HC1112C113C1i30-6013 HC Col2C1i3 Ca113 0-7x1x3.B4 Only 9.B10 HI 5 ΩCM3I C112CH, C13C1'12 (Ph) C13Cii3II Cll3QJ 03 C H3H(:Ei3 0-3 0, σ3 Hα3Q-6 CB, CM, HCB50-7 α, CM, II C1130JS C1l, CB, II Cii, α2(2-Taih)0113CB311 C1 f, Cl2(2-CIPb) CH3013B 0f3012(2-(01,) Ph)013 CFI3 B Of3 012 (2,6-Cl2Ph) C1i3 C1 (, II CH, 012 (2-bili ψ) Oil, C1! 301 CH, 012 (Ph) Table 7 X and Y are C (R3) 01') OR "R" (unless specified) B3 -R' !l9-1!"HI5.0 h) IE Cy12el13CB2CH3013C12 (2-BrPb) ifB OiCm, CFI, Ql, Qi, Qi2(2- (C1!,)l'h) 11!I 012Of, 0120f301.CHI 2(2-(OCll,)I'h ) IIi!c ′q3 Lolico 3 Mouth 3 Mouth 2 (2-(α)Ph) HB (:3CB2C11, C1i, Of2(2-(σ, )Ph) 1fIIC---H, Cm2C113 Mouth 3 α2(2- (QCchi)ph) TomiB 012cH,01201,0f3elf2(2-(Sol,)! 'h)' HB CH2Cl'I, Chi20il, 01.01. (2,6-,-ff)yoPh) HB Oi2(II, CH2CH3013(:B2( 2,6-(C1)21'h) MII 012C1i, CH2Cm3 C1l, CB12(2-Bi+J, 9.z) '1nif e112eB3Ci120 ra 口!, Cl2(2-thiophenyl) HTi CH2c'I!30choF1 x CH3C)!z (2-i7kitsu-force)7shi) iiB 012el13 C112C! I, CHI3 CB2 (2-pyramine:, 11/) HH0 is 1 3 mouth 20f, CB3 α2 (Phl ifBl” 13gB’ 19g110 B50 !Co Ko Yo Yo! Ko Yo Yo YoE" B3MP' E9 discharge 10E50 B11 B II 013CE2 (!'h) BBflHCH2O-I II E RHC130J H 8813C1130-6B HHHolI30-7H HHHC3i3QJ5 M II Cm3 CH30130!2 ( 2-Pi IJ97) ME 01.C1 !301 .CH2(Ph) RHcB3cH3C2f30J B 11 01301.Cll30-3 B11 0!, C1130130-6 ifHOf, 0!, Oi, t>7.

B C13cIi301. 0-1s II0! , C1i, CHI3C! I□C 1,C1i, CH2(2-rPh) ll01.012CHI3CI! 2Ci l, 01,012 (2-CIPkt) BC13el12ell, CB, Cll 333 (B2 (2-(01,)Pb) HCm, 022Chi3Cm2C113 C13CH2 (2,6-Cl2Ph) H013012CM3CII2CM, 0 13Ci+2 +2-CF,!'k) lin113-R4B9-810 B5 QzCE3C1'12C1(3CR2α3 α3 0(2-tetrahydropyra C013CB2CH3CB2CH3013CB2 (2-pyridi11z) HOf3CEC13Chi2C113CH3CBfPh) HCH3CH2 01,0112C1i3CH30-4HCB3C1i2CH3cFI2C"E3 CHI30-3, l IC1l, 01.CM, Cm2CII, Cif3 0-6 HCM3Ci12CH,CI!2013CI'!30-7 11CB, 0112CIO3CIl□C13el !, 0-45, 11CE2CH3C H2C)13 CB2CH3CH3(B2(2-FPh) IICI(2C'F 13 C112C)13 CB2CH3C'R3CB2(2-C1Ph) H0030C113Cill mouth, α3 Mouth (2-(α,) Ph) !'!0 !201I, Q12C1l13012013011.0f2 (2,6-Cl 2Ph) 1IC112013Cm2CII3 011:'H3013012 (2-Piri-Fure) 80!2C713C1li2CH3C112CE30f3 CH2(Ph) HCHl2CR3012C1301,0f3CB30J 1I C)!2013CE2CM30i20f3CH3Q-311CH0f3cH2 CH3012CB3cB3Q-611012C11301120 !3cH201 30130-7HO203 Loli: 11.01.Cm mouth, o-xs aB" R3-R'! 19-R" 15Q CI (3HCR3CH2 (2-Cr3Ph) HB CB3 B Cif3 0i2 (2-f trahydropiraf) HII C B3 11 013 Cr12 (Z-pyryttJ aE 013 II CB 3 Cl2 (Pb) IIE CB3 HCH30-I H B cH, HCB3 Q-3H HCM3mII CH2O-6II Flop3 III QJ3 0-F HH013III C113Q-15I IolI38 01. 0f3C1l!2+2-rPh) HCl13 1!CB3 ell, CB2(2-CIPh) l lCH3HC1i, CEI, CB(2-(CB3) Ph) BCB, HcE, C11130i2 (2,6-C1I'h) HCl13 I CB3 CB, 012 (2-C3P h) !iIJ, !!CB, 0130i12 (1'h) lICl3 R C113CD3 QJ B CIi, I O13C H , OJ IfCii, II Of, CH3O-6 BCB3 HCH3CB Q-7H CH,E C13CB, Q-15H 11R3=E' E9=110B" Q XCBiFI HCH3CH12(2-Pyridyl HCH3HHCm3ON2(Phi B CH3R Bi C1'!3Q- I H Cl314 HCH30-3II CB3HF!CH2O-6R CI'13HHCH3O-7H CH3HH0130-45H 口3CO,C)I, 0f3C!l2(2-FPhl 11CE,, CB, C D3CH2 CH3CH3C11!3C2!3 CH2(2-(CH3 ) Ph) BCIi30 1.CIl!3Of, CD12 (2,6-Cl2Ph) )10i301.CI'!, 013C1i2 (2-CF, Ph) !1a Ra mouth Ra mouth Ra Rho (2-tetrahydropyran) HCEI3 Cif3 CO, C113 Cl2 (2-pyri%) IICB, C113CIB, 01.low (ph) Re1l, CH3CB, CB3 0-I IIa et al. Hol, CB, CB3 013 Q-7B013CF! 3 mouthi, 0130 J5 F1N+"ll3-1' I!'-1"! i5Q 3 1Ph ) HCH3B HcIi3012T2-(OCH3)Ph) IIC) I, H11CH3Cl12(2-<0f)Pk+l HCH,HHC1i,cE 2(2-(CF,)Ph) HCI(,HHCH,C112(2-(CKj3) Pk+) Hol, HHCH3Cl2(2-(SCH,)Pb) HCl3 RHC13CH2(2-Chi57yu≧ThreIfCH3HII CB50f2(P h) Bel!311 E CH2O-I ll01, II HCH2O-3H ol, B H013Q-6!1 013 HHCif, Q-7E C'H3B 11 01.0-45 HCm3i1 HOf2Cm, CEI 2(2-FPh) HCHI3 B Htjqci, (51,C2-CIPh) IIQ13II E C11203mouth 2(2-(mouth,)Ph ) HCO3H B Cm2CII, 0f2(2,6-Cyu2ph) "C!!, I B CB31[I HCm2C113Q-3HJ!113-14 1911I!10 15 Ω m2012(2C112(BCm4 3 II H012C11 C!i2 012 (2-CIPh) HCM, if HCB2Cl, C1120f2 (2-(mouth!,) Ph) IICj (3HI f CB12C21gC112C!2 (2,6-Cl2Ph) B013 HH C112C112C1 1012 (2-pyricifre ) RCl(3HHCB2Cl , 012012(Ph) I(CI3HII CB201.CB20-4 HC 'H3HHO12Cm!, Of2 0-3 !ICM, HB CHl01.C B2O-6HCM, II it 01.C) 1.CB2O-711C! ! 3H II CH2Cl1.CH20-B5 lIC1,Cm(21f M CB, 01.?(2-rPh) R013C112H11CH3,CB2(2-CIP hl mlCM3CB2 11 E CB3 (ko12(2-(Ofko)!'h) BC13CM2 II I(C113CB2(2,6-Cl2Ph) EC7 i, Q12HI Q!, 0(2(2-CF3Ph) ECB3CM211 I I CB, 01.(2-tetrahydropyran) HCM3c112 1!H Of3 CHl2(2-Biri)y mCR30+2i1 B 0130f2 (1'h) IC113CE2E E Q!3O-1BQ!, 0f21!B CB3'Q-3m1C1l, 0211 C'II3 White HCl1.CB2 H B CB, O-7 Iris C Ko (KoClI2 H11 (KOI3 OJ5 !1x1B 3.14 B9410E5 Ω Ward CM3CH, CH3CH3Cl12 (2-F Ph) IIICH3C"H3elf3CE3C1 (2 (2-C1l'kt) HCl13CB, CH3CH3012 (2-(CB3)Ph) 1101 , 0i13 CM, 01 .012(2,6-Cl2Ph) HOf, CH, 0f3CH3(B2(2-σ, Ph) 11013eJI, Ca13 Mouth I, 01. (2-tetrahydropyran) (B3 (B3 CHl C'R, CB 2 (2-bili9y) B013 CHl3 CH, CM, 0f2 (Ph) 11 mouths I, CR3C1i, OJ 1 mouths Mouth Q-3 if a!30!3C1i3 (J, Q-6EC1i3 CB13 C1i, CB, Q-) BCm3 c'l13 Of3 CB3 0JS B mouth i, C'R 2C!!3 C1120f, C1130i2 (2-FPh ) 8 mouth to mouth low C11301301 (2-C1Ph) B013 0r2CB, C 1iCH,013012 (2-(01,)Ph) Hol, 0120I3 Cm mouth to mouth CH2 (2,6-Cl2Ph) HCH3CB3 01. C H,Of2(2,6-(F)2Ph) 1101, 0i2C113CM2O1 ,01301,(2-pyridyl) B013 0I2CM3 CB, ell, Chi, B12(Ph) H(ff3 012CH,0f20 et al. Q- I 1 Mouth et al. CM2O130120 et al. Of, Q-3!! Mouth I, 0f2CB 3 0f2elf3 Mouth I, O-6lICB5 0!2CB, C112C1 3C1i, O-) EC1i, CH2013CH120 et al. 013 0-4 5 HOf, C1120f 3 012CH, 01, Of , (2,6-(r)2 Ph) Hol, CO3CB20f, CM, 01.CB3 Cal, (2J ) h) IIQ1201.012C1i3 0120 et al. 03 Low (2-C IPh) lIC1i201.CB2C113C1120!301!3CB2 (2 -(CIi31!'!l) H("11!, CH, CR, C1f3CIi2 C1'!, mouth], C112(2,6-Cl2Ph) Ffl" B3.R' R9=E" B5OXCM2CH3O12CHI3CEI2CB, CH3C l2(Pk+ ) !IC) I2CHl3 O12Cm!, C12!'h 01 .OJ ll0f, CM3C112CB3C120f, 0130-3, HCH2C13C12CH3CM2CB3Cm3Q-6HCM2CM3012C hi3C1lσ3 mouth, Q-711 mouth M2CM, CBll2CR3C12 OH3C1130-15110313H03σ2 (24Ph) $ICM, C O31!Of, 012 (2-CIPh) El1m'H3CM3! I CH 301, (2-(CO,)i’h) IICH3CM3! i CH3Cl2l2 (2,6-C121'h) lIC113CH3HCH3CH2 (2-BiliF ) BCm, cH3B Of, 01. (Ph) Hα, C113HCl3 0-L H CM3CM3II 0130-3 H CR3CR3II Cm30-6 11C13CB, HCII, O-71f C1,CB31f CB50J5 lIC1311013CH,CB12(2- FPh)! IC131f CII, CB, C1l(2-C1Ph) lI C13B 0130f3(II2(2-(013)Ph) m1CH,II CE, 0f3012(2,6-C12!'h) !!(:B3OCB13C11 3CE2(Wb> BCH3B CB5013QJ If RIB344!1911BIOR5Ω CH3HC1j3CH30-311 C143HCB, CB13Q-6IIca3 g cyo, 013 0-] HCl113M 0f3C2130-1511013I C II, Cl3CH , Cl12(2-n'h) IIc'113H(m2CH3013CB2(2-CIPh) IICU3B Cl112CO,C113CB2(2-(CH,) Ph) 11σ31'I CB(mouth 3 QJ mouth 2(2,6-Cl2Ph) Ffl:m3If Cji2CM3CM, C112(2-C12!'hl 1 口ら 口らab ah 0 -(2-tetrahydropyran) HCm I C11 2C1lr, 013 3(2-pyridyl) HCH3HCB2O-, C1 l, CHl2(f'h) B013 HCM2CB5 Of3 QJ HCM 3 HCB2Cl13 Mouth Q-31fC113HC1120 f3C1l, X-6m1CB, E 012CH301 , Q-F Hol, II CB2O et al. Low, 0-15 wa-mouth (, CB, mouth et al. C112 (2-rf 'h) 11CB, CB3 013 01.Of, Of, (2-CIPh) HCl13CB, CB, CB5C113012(2-(C1i,)Ph) IICj, C1I3C)l, C113口i, 32(2,6-C12!'h) IfCI!2C13C1,0130!, C112(2-(T, I'h ) IICH2CF, 3 013 Of, Of, Of2(2-7) Rahit”d Pi (Ran) H012C1i, CH3C1l, CHl 32 (2-Bili-Fre) 8-chira-ro, CB, Chi, Of, CH2 (1'h) RCII2C B3 mouth-ra-mouth, Of3 0-I HClI20 et al. 03 03 mouth-ra O- 3! IC112CH, CH3CH3012, O-61CR2C1!3 Mouth! 3 C1l, 01. O-7H01201301, e113CB30J5 III lx, 3,4 R9~! 17LD B5 Ω λ1i HHCH3Cl12( 2-rPhl HTl )l HC1(3C'j12(2-CIPh) BHI I Fl cE, cE(2-(Of3)f'h) EliI II it 013CM2(2,6-C12!' hl ifHHH0r3(B2(2-(T, Ph) II!!!!HG13 CI+!2(2-7 trahytropyran) B HHCIi, 012(2-pyridyl) HII B HCH3Cl1!2 (f'h) IIIHHH mouth B4 B HHHCE, O-3H Hfl III 0f30-6 H N 11 E 01. Q-711 HM B CB3QJ5 111 Table 8 CM, 012 (2-(lPh) 013Ti 1!CB2o!, CH2CH3CH3012(2-!lrl'h) 01°E II (:E2 C11I3C1112CB30f3e112(2-(Of,)Ph) CH3I HC12CI, 012013CI!, 01212- (OCH,) Ph) C 1l, RB CB2CM3C12CE3C'H,012(2-(CM)Ph) CM.

B RC’R2C’EI3CH2CB3C1ll, CB2(2-(CF,)Ph ) 01゜III II C82CH3, CM2C1!301. C112 (2 -(OCr3)Ph) 01.11 HCB2C1+, 012013Cm301 2 (2-(SCE,)Ph)　01゜if　11　cB□0113CR□C! 1 ．． C1! , Mouth 2 (2,6-(F)2Ph) 01゜II　II　C112CB ,0f2Cl,CI(,012(2,6-(C1)21-h) 01°11H 012CH, C112CR30f, (B12 (2-pyri-dyl) 01゜EI HOf2CB, CH2Cl13 013 012 (2-Fla>shi) CB.

HH01,Of, C82CH3013C112 (2-tetrahydrofuran) mouth UHH012C! 13CE2CB, CM, 01□(2-tetrahydropyran ) cs.

B If C82CH3,CI(2C7(,C1301,(2-thiophenyl) KO311 HCH2Cl3 CH2Cl, CB3 mouth (2-isokizuso1 no Le) 013II II CM2O11, CM2C) B3 CB, el+ ( 2-pillar) zshi) C113Xi IIllCH2O13CE2CH3C port 2 (Ph)　C)13E”E2E3E’　H5OM8 C)l　CM2C)13CH20(3CM30-I　CH3I　HCM2CM3 C1 (, Cm3CR3Q-3CH3I E 012C) I3CB2CB3CE3 0-6 CB.

11 B CM2C Town CI (2CE3 CH30-7CM.

11 Hoi2CH, C112CE3CH3o-xs’ CE3II HCM 2CH3O12CE3C12Cl, C112(2-FPh) Loli 13) I RQ12CI (301,013C'112CB302 (2-CIPh) 012 CM.

III HCH2Cl, CE2CI13el1243 α2t2-(Ca3)p h) G2C3HH012CH, C11□033213 32 (2,6-C1□ Ph　CR2G2α3HH012CH3C1(□C113C113cH2C ! 2 (2-CF3Phl (m2CM3E HCl2C) + 3012013CH 2CR3Cf12 (2-tetrahydrobilane) cn2cu3B)i CH2 03H RHCH2Cl3C'H2α3C HH IJ2CH3C)! □13CE201, Q-1 = 203B) IC 82CH3 α2G3 Loli m+(3Q-3 0(2α3a H Cl□C)1 3cH2C713CH2c1 (3Q-6 0+20I3II H CB2CH3 CM2CE3CH243CH3C-7 G513H H C) I2CM3CH2 Cm, α2C1i, Of5 α2α3H H C)+2CH3C142CM 3C12C) I=CH2C! ? 2 (2-rPh) CH2C1 (=CH2H I i C) 12C83C1 (2CR3C'!!2αbe12G2(2-C1l'h ) C’H2CR bar J2H H C1 (2C13 G2 (m3Cm20+-CH 2 G2 (2-(43) Ph) 2Cl-CM2H 1 (CH2CH3C HzCB3CIII2 (H-CH2 C712 (2-6-C1zPh) Cll 2CHxCH2E H c'R2c'yi3a], C'IfzCT1=C'T lz CIPIz(P!++ 02o field 2R EI CB2C1(3(m2C 1 (, Cl2CE1.CB20J CM, CH-O42BE Loli 13 mouth 21 3 G20=mouth 2 Q-3 α20 Bako 2It H CH2CE3012CE3 02CR. tOI20-15 Cl2Cl-CE2B1x2 x3 is breath 5 Ω x8 H　H　H　H　C13　C’H2(24Ph)　CH3I　H　H　H　Cl 3Cl2 (2-CIPh) Cll3H H B1 E [Oi, mouth (2- (G3)Ph) α3II! 11 Ii C1113 CH2 (2.6-C Yu2vh) C113HE BH Port 3 CH2 (2-CF3Ph) Port 3B If fl H CM, C1i□ (2. Tetrahydropyran) C1! .

H H! ! H CB3 CB2 (2, Piriji 71/> 01.

llI H R B CH3 0!2 (Ph) CB (.

1iH! 'l I'I Ca113Q-I C113-1!11 R 11 CH3 0-3 Town HH E H C113 Q-6 RoraHHHHCB3 Q-7 03 11 B H B C113 Q-15 CH31'! B FJ if Q-C Ji, 012 (2-FTh) GN2ON31’i E H E CR2C1 (, Mouth!, (2-CIPh) CB12CH3MII B B Low C1 (, C112 (2-(mouth) p),) CH2O et al H ml 11 H 0N2C B, CB2 (2,6-Cyu2Phl CH2Cl.

II it B ml CJi2Q13 Cl2 (2-CF,!’h) C11 2CI.

! ! H E R Cl2CB3 012+2-tetrahydrobilane) CH2 03H H Ff it (:H2CM3 02 (2-Viriditare) tyx2 cm3$I B if II CH! 20 et al. CH2(Ph), 012013 BH HH CJi20! , Q-I CXl2CB3H BH B 0 12el13 0-3 CP! 201.

H II H II Cl12Ci! , Q-6 CIl, C1l.

II II II H C7i, cE, Q-7 Of, CI.

H B H II o! 20i, 0-15 012C1l.

II M 113, 013 Of, CB2 (2-FPh) 01.

II mI Of, 01, Low 012 (2-CIPh) CIi.

II II Ol, Of3 CH3 Low (z-(o et al) r red) CHll H 013 CB, Of3 CE2 (2.6-Cl2Ph) CB.

B Ii CH3 013 CIi, C’B2 (2-CF3Ph) CB3C l1 B12 B3 B14 B15 Ω E8II 11 CI, C113 013CB2 (Pal) 013B if C:B3 CH3CB3 Q-I C11311B CH3CB3 C1!3 0-3 r:B3B II (:X 3C113CII30-6 01311 ROof3 CR3(:II3 0-7 0f3B HC13CB3CH30-15C113013CB, C’) I2C B,, Cl203CH3C'H2 (2shiph) C113C113C! I, O 12Cm3CII2Cil, CB, CB2 (2-C1f'h) C1i30C1 13013C□C13C1'! □0f3C1l, 0f2 (2-(mouth,)Ph) 0i3CH, CR3Cl2C1l, mouth 20301. CH2(2,6-Cl2P fi) CIi CoCa13013 CB2O13el12CO3CB3 CIl 2 (2-Birisocre) ox.

CM, σ, CB2O30203C1l, CB2(Phl mouth 3CM3C13(m , CM3el120!30f, OJ C113013CB30f, Of, 0f2 C1(30130-30!3013CE3012013CB□CH, Cil, O -6C’ji.

Cm3 CB3 CB2Cl, 32C1! , C’B, O-] CC113 013C, CH2CH301, CM3C1i30-15 CB.

Cm3Cm3C113013013Cl12(2-Cm3CCIl!.

013 CM, CJf, 013 Cl13 CB2 (2-C1!’h) C Horizontal 01, 01. 0i301. 01. CI! □(2-(01,)Ph) 013CM, CB3 C'Ii3 C113CM, Cl2 (2,6-C 2p h) CH3Cl1. CIl3 0113 CH3CB3 CH (2-Billy Fre) CIl.

cB3C113cH, elf, C1l, 012 (Ph) C1130f3C' H3CH, CH, CB50-I CB.

xl x2 13 14 x5 Ω R801, C113ell, CIl3 CB3 Q-7ot.

e113CM3Cm3C113CH, 0-Xs CH3ell□ell, C11 □013012CH! , 012 (m, CH, 012 (2JPh) 01°G20 3 α2α30□σ302α3 Mouth 3 G2 (2-CIPh) Mouth 30120! , 012CB13 α20,0□mouth 3 mouth, ko2(2-(mouth,)i’h) mouth 3C i12C1113(:H2CH3C1i2C113C1l12C1i3Cl, C l2(2,6-Cl2Ph) or31:'8. C) I3C112CM, -P3 Mouth 2α3C13Q-1G3012CH, CR20130f2013012C1 ! , CB, O-301゜CM2Chi3012CM3012C13012C1 ! , C13Q-a 01゜CB2Cl, α2α3 α20,0□co3 G3 Q-7 mouths.

CM2C13CI+□013CB2CB3el1201. CB50-15C 1i.

CB3 ("1138 B, 013el!2 (1'h) Oi3CM301. HH013C! 12 (2J!’k) CB.

01, CM, 11 II C113012 (2-(CH3)Ph) 01゜0 1, C1l, If II CH, 012 (2,6-Cl2Ph) 013CM 3CM, il B CH30J Cl03C1l, 01.　C11,Of, C113CB1□(!’h) (ko(ko01, C1l, C1l, 013 Cl, 012 (2-F’Ph) 013CB30f, 0f3C1130130 12 (2-(013)Ph) CM.

CB3 C11301, CH, CIl, CIl2 (2,6-Cl2Ph) C I.

Of, c113Of, 01. 0f30-3 01゜口1,01. 0120 13! I H013Cl□(!’h) C13C1i2C130f2C1l, I I I CB, 012 (2-ri'h) CH3Cl1. CM, C1f2013 B II 013012 (2-(C1i,)Ph) CIl.

CM2O13012CH3B B 013C12 (2,6-Cl2Ph) 01 3CII2elf3CB2CB3B HCm30-3 CB3 undiluted agent and carrier Handbook of In5ectide Du stDiluents and Carriers) J, 2nd edition, Drandb Listed in Socs, Cardwell, New Chassis, but other solids Natural and synthetic solids can also be used. For wettable powders and concentrated powders. Furthermore, diluents that are adsorbent are preferred. Typical liquid diluents and solvents are Marsden, “Solvents Gufde J. , 2nd edition, Interscience, New York, 1950. 0 ．． A solubility of 1% or less is suitable for concentrated suspensions, which are preferably kept at 0°C. It is stable against phase separation caused by McCacheon Detergent and Emulsion Yearbook (McC utcheon’s Detergents and Emulsifiers Annual) J, MC Publishing Corporation, Ridgewood New Chassis, as well as Sysely and food. ), “Encyclopedia of 5 surface A Active Agents) J, Chemical Publishing Company Incorporated, New York, 1964, Surfactants and Recommended Uses is displayed. All formulations are free from foaming, caking, corrosion, and microbial growth. Small amounts of additives may be included to reduce

The manufacture of such compositions is well known. For liquid formulations, simply mix each component. Manufactured by. Fine solid compositions are produced by hammer mills or fluid energy mills. It is manufactured by compounding using a mill and generally grinding. The suspending agent is Manufactured by wet milling (e.g. Littler, USA) See patent 3.060.084). Granules and tablets are preformed granules containing the active substance. It can be produced by spraying onto a carrier or by an agglomeration method. J , E. Browning, “Aggiomerati on) J, Chemical Engineering ering), December 4, 1967.147ff and “Berry’s Chemica Perry's Clemical Handbook Engineer’s Handbook) J, 5th edition, Matsuf Groler Hill , New York, 1973.8-57ff.

For further literature on formulation techniques see, for example:

HM, Loux, U.S. Patent 3.235.361. February 1966 15th, column 6, line 16 to column 7, line 19 and Examples 10 to 41°R, W, Luckenba Luckenbaugh, U.S. Patent No. 3.309.192.5, line 43~ Column 7, line 62 and Example 8.12.15.39.41.52.53.58.13 2.138~140.162~164.166.167.169~182° H, Gysin and E, Knusli, US Patent 2, 891゜855.3 Column 66 to 5 Column 17, and Examples 1 to 4゜G, C, Clear Klingman, “Weed Control as a Science.” ol as a 5science) J, Joan Willey & Son Incorporated, New York, 1961. pp. 81-96.

J. D. Fryer and S. A. Evans; "Weed Control Handbook" J, Blackwell Scientific Publishing, Oxford 1968. pp. 101-103.

In the examples below, all parts are by weight unless otherwise specified. 2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,11hebutane 60% alkylnaphthalene sulfonic acid Sodium 2% Sodium ligninsulfonate 2% Synthetic amorphous silica 36% The active ingredient is first sprayed onto the amorphous silica, then the ingredients are blended and all solids are removed. Hammer mill to essentially 50 microns or less, recompound, and It was packaged.

2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,1]hebutane 50% alkylnaphthalene sulfonic acid Sodium 2% Low viscosity methylcellulose 2% Diatomaceous earth 46% The active ingredient is first sprayed onto the diatoms, then the ingredients are blended and roughened with a hammer mill. Grinding and then air milling to produce particles with essentially all diameters less than 10 microns produced a child. The product was recompounded before packaging.

Hydrating agent of Example B 5% Acpal guide particles (US standard sieve 20-40 mesh, 95% 0.84- 0.42mm) A slurry of wettable powder containing 25% solids was added in a double cone mold. It was sprayed onto the surface of the Coupal guide particles. The particles were dried and packaged.

2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,1]hebutane 40% Atrox 3403F 3% Atrox 3404F 3% Xylene 54% The active ingredient and Atrox emulsifier are dissolved in a solvent, filtered and packaged. Ta. Atrox 3403 and 3404F are ICI Americas Inc. Anionic and cationic surfactants manufactured by Ted.

1(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7-o Xabicyclo[2,2,1]hebutane 5% Acpulguide particles (US standard sieve) 20-40 mesh, 95% 0.84-0.42mm) The active ingredient is dissolved in the solvent and the solution is passed through the dedusting particles in a double cone formulation mold. was sprayed on. After spraying the solution was complete, the material was warmed to evaporate the solvent. material was allowed to cool and then packaged.

abduction 2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,1]hebutane 50% Wetting agent 1% Crude lignin sulfonate (contains 5-20% natural sugar) 10% Acpalguide Clay 39% The ingredients were blended and ground through a 10o mesh screen.

This material is then added to a fluidized bed granulator and the airflow is adjusted to gently fluidize the material. , and a fine mist of water was sprayed onto the material being fluidized. of desired size range Fluidization and atomization continued until particles were produced.

Spraying has stopped, but fluidization can optionally be done using heat until the water content is at the desired level, typically continued until it was reduced to less than 1%. The substance is then discharged and sieved to dilute it. Desired size range, typically 14-100 mesh (1410-149 microns) ) and packaged for use.

2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,1]hebutane 25% xylene 25% Atrox 3404F 5% G1284 5% Ethylene glycol 8% Water 32% The active ingredient, solvent and emulsifier were formulated together. Add this solution to ethylene glycol and water with stirring.

2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7 -Oxabicyclo[2,2,1]hebutane 5% water 95% The compound is added directly to water with stirring to produce a solution, which is then packaged for use. I was able to

2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy)-7- Oxabicyclo[2,2,1]hebutane 10% Attapulguide 10% Pirophyllite 80% The active ingredient is sprayed onto the attapul guide and then passed through a hammer mill to All produced particles of 200 microns or less. The crushed concentrate is then powdered pyrophyllite until homogeneous.

Satonuri The test results show that the compounds of the invention are active post-emergent herbicides and especially pre-emergent herbicides. Which indicates that. The compounds of the present invention can be used to treat selected grasses and broadleaf weeds. For example, alfalfa (Medicago 5ati) is useful for va), barley (HordeuIIlvulgare), corn (Zea ll1ays), cotton (GossypiuLllhirsutum), horsefly Rana (Brassicanapus), Rice (Qryza 5ativa) , soybean (Glycine max), sugar beet (Beta vulga) ris), and important agricultural products such as wheat (Triticus aestivum). It also has resistance to industrial crops. The violet and broadleaf weed species that are controlled include: Includes but is not limited to: Echino chLoa crusgalli), black grass (A lopecuri) smyosuroides), crabgrass (Digitalfa spp,) , Setaria spp., Chenopod ium spp, ), teaweed (Sida 5pinosa), Cyperus difformis, and water chestnut Snut (E1eocharis spp, ). Several compounds in the present invention The plant is used to control field and paddy field cattle grasses and selected broad-leaved weeds such as black moth. Particularly useful for the conditioning of spears and water chestnuts.

These compounds can be found in certain areas, such as around storage tanks, parking lots, highways, and and railways, fallow crop areas, and fruit trees and cultivated crops such as bananas, coffee, It also has utility for weed control of selected plants in oil and rubber. On the other hand, this These compounds can also be used to alter plant growth.

The rate of use of the compounds of this invention is determined by many factors. These factors include; The formulation chosen, the method of application, the amount and type of plants present, the growth conditions, etc. Included. Generally, the compound is used at a rate of 0.01 to 20 kg/ha. The preferred usage rate range is 0.03 to 1 kg/ha. go Although some compounds do not exhibit herbicide activity at the application rates tested, these compounds is predicted to have herbicidal activity at higher application rates. This technology Experts can easily determine the rate of application needed to achieve the desired level of weed control. .

The compounds of the invention may be used alone or in combination with other commercially available herbicides, insecticides or fungicides. Can be used in combination with vinyl. The list below is for use in mixtures. Some examples of suitable herbicides are given below. Compounds of the invention and one or more of the following: Combinations with herbal agents are particularly useful for weed control.

Common name: Chemical name Acetochlor 2-chloro-N-(ethoxymethyl)-N-(2-ethyl-6- methylphenyl)acetamidoacyfluorophen 5-[2-chloro-4-( trifluoromethyl)-phenoxyco-2-nitrobenzoic acid Acrolein 2-propenal Alachlor 2-chloro-N-(2,6-ethylphenyl)-N-(methoxy methyl)acetamide Anilophos 5-4-chloro-N-isoprobil-ruvanilloyl-methyl-〇 , O-dimethylphosphorodithionide Ametrine N-ethyl-N'-(1-methylethyl)-6-(methylthio)- 1,3,5-triazine-2,4-diamine Amitrol IH-i, 2.4-1-lyazole-3-amine A MS Ammonium aslamic acid rufamate [(4-aminophenyl)sulbonyl]- Methyl carbamate Atrazine 6-chloro-N-ethyl-N'-(1-methylethyl)-1,3, 5-triazine-2,4-diaminepalpan 3-chlorocarbamic acid 4-chloro rho-2-butynyl Production: Raw Efuyu Benefin N-butyl-N-ethyl-2,6-sinitro 4-(trifluoro methyl)benzenaminepensulfuron 2-[[[[(4,6-cymethoxy C2-pyrimidinymethyl)aminocomethylcarbonyl]amino/]sulbony ] Methyl J benzoic acid methyl ester Bensuride 0.0-bis(1-methylethyl)S-[2-[(phenylsulfonate) Nyl)amino]ethyl]phosphorodithioate Pentacine 3-(1-methylethyl)-(IH)-2,1,3-benzothia Diazin-4(3H)-one, 2,2-dioxide Benzofluoro N-[4-(ethylthio)-2-(trifluoromethyl)phene Nylcomethanesulfonamide Benzoylprob N-benzoyl-N-(3,4-dichlorophenyl)-DL -alanine Bifenox 5-C2,4-dichlorophenoxy)-2-nitrobenzoic acid Chill Bromacil 5-bromo-6-methyl-3-(l-methylpropyl)-2,4( IH, 3H) Pyrimidinedione bromoxynil 3,5-dibromo-4-hydro xybenzonitrile Common name: Chemical name Butachlor N-(butoxymethyl)-2-chloro to N-(2,6-dimethylethyl chill) acetamide Putidazole 3-[5-(1,1-dimethylethyl)-1,3,4-thiasia silyl-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone Butraline 4-(1,1-dimethylethyl)-N-(1-methylpropyl)- 2,6-cinitrobenzeneamine butyrate bis(2-methylpropyl)-power S-ethyl rubamothionate Cachophosphoric acid Arsenic acid dimethyl oxide CDAA 2-chloro-N,N-di-2-propenylacetamide CDEC 2-chloroallyl diethyldithiocarbamate CGA142,464 3-(4,6-Simethoxy1.3.5-triazinyl-2-l)-1-[2-( 2-Methoxyethoxy)-phenylsulfonylcourea Chloramben 3-Amino-2,5-dichlorobenzoic acid Chlorbromulon 3- (4-Flomo-3-10lophenyl)-1-methoxy-1-methylurea Common name: Chemical name Talolimuron 2-[[[(4-chloro-6-medoxy 2-pyri□ ethyl 　midinyl)ethylamino]carbonylcoamino]sulfonyl]benzoic acid, ethyl luester Chlormethoxynil 2,4-dichlorophenyl 4-nitro-3-methoxyphene nyl ether Chlornitrophen 2.4.6-)IJ chlorophenyl-4-nitrophenyl ether Chloroxuron N'-C4-(4-chlorophenoquine)phenyl E-N, N- dimethyl urea Chlorpropham 1-methylethyl 3-chlorophenylcarbamate Chlorsulfuron 2-chloro-N-[[(4-methoxy-6-methyl-1,3 ,5-triazinyl-2-yl)aminocarbonylcobenzene sulfonamide Chlortoluron N'-(3-chloro-4-methylphenyl)-N,N-dimethy luurea Synmethyline exo-1-methyl-4-(1-methylethyl)-2-[(2- methylphenyl)methoxy]-7-oxabicyclo[2,2,1]hebutane Common name: Chemical name Clethodim (E, E)-(±)-2-[1-[[(3-chloro-2-prope oxy]imino]propyl]-5-[2-(ethylthio)-propyl]- 3-Hydroxy-2-cyclohexen-1-one Cromasone 2-[(2-chlorophenyl)methyl]-4,4-dimethyl-3- Isoxazolidinone Chloroxydim (E,E)-2-[1-[[(3-chloro-2-propenyl )oxy)-iminocobutyl]-5-[2-(ethylthio)propyl]-3-h Droxy 2-cyclohexenone-1-one Clovilaride 3.6-dichloro-2-pyridinecarboxylic acid CMA MAA lucium salt Cyanazine 2-[[4-chloro-6-(ethylamino)-1,3゜5-tria Zin-2-yl]amino]-2-methylpropanenitrile Cycloate S-ethyl cyclohexylethylcarbamothionate Cycluron 3-cyclooctyl-1,1-dimethylurea Cyperquat 1-mer Tyl-4-phenylpyridinium sibrazine 2-chloro-4-(cyclopropyl Ruamino)-〇-(isopropylamino)-S-triazine Common name Chemical name Sibrazole N-[5-(2-chloro-1,1-dimethylethyl)-1,3, 4-Thiasiasilyl-2-cyclopropaneylpoxamide Cypromide 3',4'-dichlorocyclopropanecarboxanilide Darapon 2,2-dichloropropanoic acid Dazomet Tetrahydro-3,5-di Methyl-2H-1,3゜5-thiadiazine-2-thione DCPA 2,3,5.6-tetrachloro-1,4-benzenedicarboxylic acid di methyl Desmedifan [3-[[(phenylamino)carbonyl]oxycophenyl ] Ethyl carbamate Desmetrin 2-(isopropylamino)-4-(methylamino)-6-(meth) tilthio)-s-t-lyazinesialate bis(''-methylethyl)carbamo Thionic acid S-(2,3-dichloro-2-propenyl) Dicamba 3,6-dichloro-2-methoxybenzoic acid dichlobenyl 2,6-dichloro-2-methoxybenzoate Chlorobenzoni l-1,1 dichloroprob (±)-2-(2,4-dichloro phenoxy)propanoic acid Common name: Chemical name Diclofosob (±1-2-[4-(2,4-dichlorophenoxy)phenoki [C]-propanoic acid methyl ester Diethatyl N-(chloroacetyl)-N-(2,6-dimethylethyl)-gly Shin Cifenzoquat 1,2-dimethyl-3,5-diphenyl-1,H-birazoli Umu Dimepiperate 5-1-methyl-1-phenylethylpiperidine, -1-cal Bothioate Dinitramine N3. N3-diethyl-2,4-dinitro-6-(+=refluor methyl)-1,3-benzenediamine dinoseb 2-(1-methylpropyl) -4,S-dinitrophenol Cifenamide N,N-dimethyl-α-phj-nylbenzeneacetamide Diprobetrin 6-(ethylthio)-N,N'-bis(1-methylethyl') -1,3,5-triazine-2,4-diamine diquat 6,7-cyhydrodibi Lido[1,2-a:2',1'-C]-biradinedium ion N'-(3,4-dichlorophenyl)-N,N-dimethylurea Common name: Chemical name D　N　OC2-Methyl-4,6-dinitrophenol DSMA MAA Nina thorium salt Zimron N-(4-methylphenyl)-N'-(1-methyl-■-phenyl chill) urea Endothal 7-oxabicyclo[2,2,1]hebutane-2,3-dicarbonate acid EPTC dipropylcarbamothionate S-ethyl nisprocarb S-benzyl -N-ethyl-N-(1,2-dimethy(SC2957)yl)-propyl)thi All-carbamate etalfluralin N-ethyl N-(2-methyl-2-propylene) Lopenyl)-2,6-sinitro-4-(trifluoromethyl)-benzenamine Ethofumesate (±)-=2-ethoxy-2,3-dihydro-3,3-dimethy -5-Benzofuranyl methanesulfonate FENAC 2.3.6-Dolichlorobenzeneacetic acid phenoxabrob (±)-1 [4-[(6-chloro-2-benzoxazolyl)oxy]phenoxy]propane Acid fenuron N,N-dimethyl-N'-phenylurea fenuron TCA Funu Salt common name chemical name of Ron and TCA Furanprob N-benzoyl-N-(3-chloro-4-phenylphenyl)- DL-alanine Fluazifop (±)-2-[4-[[5-(trifluoromethyl)-2- pyridinylcooxycophenoxy]propanoic acid fluadifop-P (R)- 2-[4-[[5-(trifluoromethyl)-2-pyridinyl]oxy]pheno Flukilarin xy]propanoate N-(2-chloroethyl)-2,6-dinito Rho-N-propyl-4-(trifluoromethyl)benzenamide Flumeturon N,N-dimethyl-N'-[3-(trifluoromethyl)-phene [Nil] Urea Fluorochloridone 3-chloro-4-(chloromethyl)-1-[3-(trif phenylmethyl) phenyl coke-pyrrolidinone fluorodiphene p-nitroph phenyl α,α,α-trifluoro-2-nitro-p-tolyl ether Fluoroglyco 5-[2-chloro-4-(trifluoromethyl)fephene [Noxy]-2-nitrobenzoic acid carboxymethylfluridone 1-methyl-3- Phenyl-5-[3-(1-lifluoromethyl)phenyl]-4(IH)-bily Jinon popular name Kaefuyu Fomesaphene 5-[2-chloro-4-(trifluoromethyl)phenoxy] -N-(methylsulfonitree 2-nitropenzamide Fosamine (aminocarbonyl) hydrogen phosphate ethylglyphosate N- (bosbo methyl) glycine haloxyfop 2-[4-[[3-chloro-5-(trimethyl) Fluoromethyl)-2-pyridinylcooxy]phenoxy]propanoic acid Hexaflurate Hexafluoroarsenate Potassium Hexazinone 3-Cyclohex Sil-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4 (1, H.

3H)-dione Imazametabenz 6-(4-isopropyl-4-methyl-5-oxo-2-y Midazolinyl 2-l)-m-1-ruyl acid methyl ester and 6-(4-iso Propyl-4-methyl-5-oxo-2-imidazolinyl-p-toluyl Imazaviru acid methyl ester (±)-2-[4,5-dihydro-4-methyl -4-(1-methylethyl)-5-oxo-IH-imidazolyl-2-yl]-3- Pyridinecarboxylic acid common name chemical name Imazaquin l[4,5-hydro-4-methyl-4-(1-methylethyl) -5-oxo-IH-imidazoly-2-yl]-3-quinolinecarboxylic acid Imazetavir (±)-2-[4,5-dihydro-4-methyl-4=(l-methyl 5-oxo-IH-imidazoly-2-ruco-5-ethyl-3-pyri Zine carboxylic acid Ioxynyl 4-hydroxy-3,5-diaiodobenzonitrile Isopropaline 4-(1-methylethyl)-2,6-sinitro N.

N-dipropylbenzenamine Improturon N-(4-isopropylphenyl)-N',N'-dimethyl urine Basic Isouron N'-[5-(1,1-dimethylethyl)-3-isoxazolyl] -N,N-dimethylurea Isoxaben N~[3~(1-ethyl-1-methylpropyl)-5-isoxa Zolyl]-2,6-simethoxybenzamide Carbutyrate 3-[[(dimethylamino)carbonyl]amino]phenyl- (1,1-dimethylethyl) carbamate chemical name Lactofen (±)-5-[2-chloro-4-(trifluoromethyl)phenol 2-ethoxy-1-methyl-2-oxyethyl-2-nitrobenzoate Renacyl 3-cyclohexyl-6,fu-dihydro-IH-cyclopenta-pyri Midine-2,4(3H,5H)-dione Linuron N'-(3,4-dichlorophenyl)-N-methoxy-N-methyluria Basic MAA methyl arsenic acid MAMA Monoammonium salt of MAA MCPA (4-chloro-2-methylphenate) phenoxy)acetic acid MCP B 4-(4-chloro-2-methylphenoxy)butane acid MON7200 S,S-dimethyl-2-(difluoromethyl)-4-(2-methyl (tylpropyl)-6-(trifluoromethyl)-3,5-pyridine dilupotio Natemecoblob (±)-2-(4-chloro-2-methylphenoxy)-pro Panic acid Mefenacet 2-(2-benzothiazineruoxidyl N-methyl-N-phenylene Ruacetamide Common name: Chemical name Mefluidide N-[2,4-dimethyl-5-[[()lifluoromethyl)-su ruphonyl]aminocophenyl]acetamide Metalproparin N-(2-methyl-2-propenyl)-2,6-dinitro- N-propyl-4-(trifluoromethyl)benzenamide Metabenz 1,3-dimethyl-3-(2-benzothiazolyl)thiazurone urine Basic Metam Methylcarbamodithionate Metazole 2-(3,4-dichlorophenyl)-4-methyl-1,2,4-o Xadiazolidine-3,5-dionemethoxuron N'-(3-chloro-4-methoxuron) (toxyphenyl)-N.

N-dimethylurea Metolachlor 2-chloro-N-(2-ethyl-6-methylphenyl)-N-( 2-Methoxy-1-methylethyl)acetamide Metribucin 4-amino-6-(1,1-dimethylethyl)-3-(methylthi e)-1,2,4-triazin-5(4H)-one Nickname: Touda Metsulfuron 2-[[[(4-methoxy-6-methyl-1,3,5methyl -triazinyl-2-yl)amitecarbonyl]ami/]su/l/honyl]benzoin acid methyl ester M) (1,2-dihydro-3,6-pyridazinedione molyne S-ethyl hexahydro-IH-azepine-1-carbothionate Monolinuron 3-(p-chlorophenyl)-1-methoxy-1-methylurea Monolon N'-(4-chlorophenyl)-N,N-dimethylurea Monolon TCA Monolon and TCA salts MSMA MAA monosodium salt Napropamide N,N-diethyl-2-(1-naphthalenylamino)-propane Amide Nabutalam 2-[(1-naphthalenylamino)carbonyl-benzoic acid Nebulon 1-butyl-3-(3,4-dichlorophenyl)-1-methylurea Nitraline 4-(methylsulfonyl)-1,6-sinitro N.

N-dipropylaniline Common name: Chemical name Nitrofen 2,4-dichloro-1-(4-nitrophenoxy)benzene Nitrofluor 2-chloro-1-(4-nitrophenoxy)-4-phen (Triphenoxymethyl) benzene lua N,N-dimethyl-N'-(octahylene Dro-4,7-methanol-IH-intinyl) urea 3aα.

4α, 5α, 7α, 7aα-isomer norflurazone 4-chloroo-5-(methylamino)-2-[3-(+-riflu (oromethyl)phenyl l-3(2F+)-pyridazinone Oryzalin 4-(dipropylamino)-3,5-dinitrobenzenesulfona Mido Oxacyacin 3-[2,4-dichloro-5-(1-methylethoxy)-phene ]-5-(1,1-dimethylethyl)-1,3,4-oxadiazolo-2( 3H)-oxyfluor 2-chloro-1-(3-ethoxy-4-nitrophe) 1,1 '-dimethyl-4,4'-diviridinium ion PEPLATE Butylethyl carbamothionate S-propyl pestle 7 winters Benzomethalin N-(1-ethylpropyl)-3,4-dimethyl-2,6-silane Nitrobenzenamine Belfluidon i, 1. , i-trifluoro-N~[2-methyl-4-(phene Nylsulfonyl) phenylcomethanesulfonamide Fenmacifam 3-[(methylsulfonyl)aminocophenyl(3-methyl phenyl) carbamate Pichloram 4-amino-3,5,6-dolichloro-2-pyridine-carboxylic acid PPG-10135-[2-chloro-4-(trifluoromethyl)-phenoxy ]-2-Nitroacetophenone oxime-〇-acetic acid methyl ester Pretilachlor α-chloro-2,6-dinithyl N-(2-propoxyethyl ) Acetanilide Prodiazine 2-[[4-chloro-6-(cyclopropylamino)-1,,3 ,5-triazinyl-2-amino J-2-methylbrovanitrile Profluralin N-(cyclopropylmethyl)-2,6-sinitro N-pro Pyr-4-(+-lifluoromethyl)benzenamine Common name: Chemical name Prostone 6-medoxy N, N'-bis(1-methylethyl)-1,3, 5-triazine-2,4-diaminepromethulin N,N'-bis(1-methy (ethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine Pronamide 3,5-dichloro-N-(1,1-dimethyl-2-brovinyl) base nzamide Propachlor 2-chloro-N-(1-methylethyl)-N-phenylacetoa Mido Propanyl N-(3,4-dichlorophenyl)propanamide propazine 6 -Chloro-N, N'-bis(1-methylethyl)-1,3,5-triazine- 2,4-diaminepropham l-methylethylprosyl phenylcarbamate Farin N-[[4-(dipropylamino)-3,5-dinitrophenyl]su sulfonyl]-3,S-dimethylsulfilimine Propachlor 2-chloro-N-(1-methyl-2-propynyl)acetanily de Virazolate 4-(2,4-dichlorobenzoyl)-1,,3-dimethyl-pi Lazoli-5-p-toluenesulfonate Common name: Chemical name Pyrazone 5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone Pyrazosulfuron S-[3-(4,6-simethoxypyrimidiny-2-ethyl) ) ethyl ureadosulfonyl-1-methylpyrazole-4-carboxylate Quincloraf 3.7-dichloro-8-quinolinecarboxylic acid quizalofop ( ±)-2-44-[(6-chloro-2-quinoxaliethylnyl)-oxy]ph Phenoxy]propanoic acid ethyl ester Secbumetone N-ethyl-6-medoxy N'-(1-methylpropyl)-1 ,3,5-)riazine-2,4-diamine Setoxydim 2-[1,-(ethoxyimino)butyl]-5-[2-(ethyl thio)propylgol-3-hydroxy-2-cyclohexen-1-one Siduron N-(2-methylcyclohegycyl)-N'-phenylurea ummazine 6-chloro-N, N'-diethyl-1,3,5-triazine-2, 4-diamine 5K-2331,-(α,α-dimethylbenzyl)-3-(4-methylphenyl )urea Common name: Chemical name Sulfometuron 2-[[[(4,6-dimethyl-2-pyrimidinyl)methy -Aminocholyponyl]amino]sulfonyl]-benzoic acid methyl ester TCA trichloroacetic acid Tebutiuron N-[5-(1,1-dimethylethyl)-1,3,4-thiasia syl-2-yl]-N,N'-dimethylurea terbacil 5-chloro-3-(1, 1-dimethylethyl)-6-methyl-2,4(IH,3H)-pyrimidinedione Terbuchlor N-(butoxymethyl)-2-chloro-N-[2-(1,1-di methylethyl)-6-methylphenylnielacetamide Tetrabutylazine 2-(tert-butylamino)-4-chloro-6- (ethylamino)-8-) riazintylbutol 2,6-theter diary Butyl-p-)lylmethyl rubbermate Tilbutrin N-(1,1-dimethylethyl)-N'-ethyl-6-(methyl thio)-1,3,5-1-clu2.4-diamine Dark name: Jiao Zhufuyu Thifensulfuron 3-[[[(4-methoxy-6-methyl-1,3,5-methyl thyl-triazinyl2-amino]carbonylcoaminoJsulfonyl]-2 -thiophenecarboxylic acid methyl ester Thiobencarb S-[(4-chlorophenyl)methyl]jetyl Rubamothio Eight trialate 5-(2,3,3-1-dichloro-2-propenyl)bis(1-methane) ethyl) carbamothioate tribenuron methyl 2-[[[[N-(4- Methoxy-6-methyl-1,3゜5-triazinyl-2-l)-N-methylamino Co-carbonyl]aminocosulfonyl]benzoic acid methyl ester Triclovir [(3,5,6-dolichloro-2-pyridinyl)-oxy]acetic acid Tridiphane 2-(3,5-dichlorophenyl)-2-(2,2,2-tric loloethyl) oxirane Trifluralin 2,6-sinitro N,N-dipropyl-4-(trifluoro methyl)benzenamine Trimeturon 1-(p-chlorophenyl)-2,3,3-to-1,1 methylsulphate urea 2.4-D (2,4-dichlorophenoxy)acetic acid common name chemical name 2.4-DB 4-(2,4-dichlorophenoxy)butanoic acid veurulinate S-probyl xylachlor dipropylcarbamothionate 2-chloro-N-(2 ,3-dimethylphenyl)-N-(1-methylethyl)acetamide The compound Herbicidal properties were found in many greenhouse trials. The test process and results are described below. vinegar.

Table 10 (1) (’8) ) C’H, CH3) I HCH2Ph C)+21Pbl Pond Exo 4. 511-4.36 (Ken, 2) 11゜1+2 3.54 +m, 2)+1゜ Engineering +2 5.32-5.06 +m, 2) +1°4.54 (6q, 2R).

3.6J, 43 (m, 2) 11° 1 Kyo 2 5.28-5.15 i-shou 2H+.

4.44 i%, 2+1).

Ko, 14 (m, 2H).

1.55-1.43 iN28).

3.15 (m, ll(+ 4 C8, CI, H) I CCR2C1111c) M2C, (i’hl drunkenness) Kiso 5.90 ++5.11 (L4.49 (dg, 2Ml.

S　C1l,CH,HH(M3CM212-rPhl　姐工Aノ　4.52　( dd, 2M), s cu, cs3HHC) 12CM1c112tz, 6-y, r h + ffL et 3, 3 (-4141゜7 CI (3CH3) IN C B, CR3C112+2.6-Cl2Pbl Port 44F (d, IHl.

s　CM3C13on　n　C)+20+3c[I□(z-rph+　ilL　E Kiso 4.5a (d, l vomit 11 shu, 45 (+1.I) 11゜2+1 4 ．． 64 ++56.1) 11゜10 elf, Cl83 Hjl CB3 0 ! 2+2.6-Cl2 ph r h’K exo 4. F3 +<+d, IF I+.

1+1 4.64 +411.1H1+1B-1+1 ratio) zz c) 13cm, mm tt CR2 (2-1rPhl fm included exo 4.56 +71. IHl.

12 ell, C) 13H) I C112+2-1rPh) "" Kino 4. 58 (d, lll+.

13 CH3CN, HHEl C112+2-CIPhl fl handling end 4J 1 fd, lHl.

14 CHI C) 13 11) I Et CH212-11rPhl? k , :c7 de 4.59 fd, 1llll, is CH3Cl13M RC)l ,CR,CB(C)+31 CM2f2JPh+ oil, z kino 5.611m, 2H1゜16　C1(ICR,n　RC'R,QC)I, CB2(2shipphl ? Niettsu 4.56 (dd*s, 4) +1゜17 c++, cy3M + 4 CM2C) I3c) I, +z-+c)+3+pb+ iMad Ekino Shizuku, 53 (Kame IH).

I@B I (el13CM, Cll3e)+2+2-(C)1,1Ph) 2d y Exhaust 7 4.6 (br, lR1゜21 11 14 C) 13C) l, C Town C) + 2 keh + 7㎥ exo 4.55 ft, 1) 11゜22 CM, CH3CN, CB3CM2CM3CH2T2-rPhl γllk-'Kino 4.59 ++1.1) 11°3.311 (dq, 2H1 23CM3C)13CH3C)l, C)l, CI(, C11, +Pbl oil, et Kiso 4.52 (dd, 1) II.

3.37fdq, 2)+1 25 II REt Et Cl, 0121Phl Oil, Exhaust 7 4.65 fm, 41'll.

:1.72 (dd, 1) 11° 26 B HEt Et CR3el+, +2.6-C3, Pbl oil, exo 4.75 (dd, 2) + 1° 4.59 (*, 2) 11° 3.7S (dll, INl.

27) I HEtEt C1 et al. 01. f2Jc1 (3+-Phl γ ridge exhaust 4.7 +m, 4H1゜2@M) I It Et C) I, C) +2 +2-FPh) Prll exhaust 7 4.7 (m, 4H1゜3.13 (dd, 1111° 29 II 11 Et 7 cm, C112+2-CIPhl oil, exo Shizu, 7 (Town 4111゜30) 1) 1 tt It CM, CH2L2- BrPhl oil, exo 4.59 fbrd, 4N+.

31)1)+tt ttC)I3c)I2u,6-r2ph+it Exo 4.561m, 4) 11゜32y HD-Prll-PrC)+3 C) +2+Phl)% Exo 4.521 Town 4Hl.

33) IN ll-Pr n-Pr C) 13C) +2+2JC) 1,1P hl oil, exo 4.50 ft, IHL.

3.65 14<1. IHl.

3.16 (s, 3H1 3511Rll-Pr ll-Pr 01. C112+2-CIPhl oil, Exo 4.59 (s, 4R1゜3.68 + dd, 1) + 1゜ C17(s, 3!41 36 8) I n-Prn-PrCR, CR212-! 1rPhl m exo 4. so (s, 4) El.

3.69 Tdd, IHL.

3.17 (s, 3111 Table 11 43 II) I) I) I CH3CN, 2-YPb: X-*n, portrait -r-+n 4.5 (d, d, 411+.

44 u) l s I4 co, ph Niji 17, @:x-w7 4.5 2 (a, d, m.

45) 1) l) + 11 C) I3 2-rPb knee V so, pond Niji ■ So 4.62 (6,1R+.

46 11 II) l RCi (2CM, 2-(to)Pb: L + So1 Pond 　3ゝ1ノ　4.46　(＜11. 目）.

3. Fu S (7141, lII+.

47 II B it I CH, C1l, Ph Extract Pond Ekin 4.5 + +s, 4111°3.4 (town, 1lH1 Table 12 Rllll C1l, H14C) I3II II CH2 (Pbl oil, :I- 7t4.64 [d, IJ11119 CP13B 11 CJI,! l II C1, (2-ffh+ oil, end 4.6 (+a, 1l1120 CR3 M　RCll5　l　l　Ci)z(2-16-(F)2Pbl　oil, end　 4J5 (d, ull, 7m (+m, 2 days).

342 (g, 3 illusions.

3.2 (s, 3R1 122 HHRc13H) I o+2+ph+ End 4.40 +d, l Il+.

123 II) I) l CM, H) I 0+2+2JPhl l’l’l "Do 4.62 (s, 2H+.

124 H+HCH2OI CM2C2-+CM, 1Phl elbow end 4 ．． 53 +11+1,281゜3.10 (m, 2H1 125II RM CH3HII CR2 (2-CIPhl mainly used 4.64 (s, 2) 11゜126) I N) I cy, HHc) I, +z, a-+r+2ph+ & End a, 61 (g, 2H+.

3,)l　(s, 3111゜ 3.20 (dφd, 2)+1 128 If II B CR, II II CR2 (2,5-ff)2Ph) 　’　vomit　a, 5G　(a, 2H+.

3.90 + starvation).

3.75 (dd, LH+.

3.33 (g,!)+1゜ 129 HII) I C83HB CH2 (2,6-(C112Phi Oil End 4.7a (da, 2) + 1゜130 C) I, HHC) 13HM C l2f2-1cH31Phl oil, end 4.63 ff1.1) 11°13 1 C) l, RII CM2C)13) I RCl2 (Phl oil 1.ln7 Do 4.65 (d, 111° 3.44 +71q, 681° 132 C113N +4 CH2CH2+1! 'l　CR2+2-FPhl Oil, end 4-7 +71.1lll.

C43 (dq, 2H+.

133 C1131+ 11 el12CI! 3ml II Q! , +2-+0 1.1Phl oil 1 end 4. sx (4, IRI.

3.42 (6q, 2R1゜ ], 2F (dφ-13H) 134 Cl431 HC112C)1. II IT C) I, +2.6-ff l, Pb) ' ' ' ' de 4.71 (t!, 1) 11° 3.42 + dg, 2) +1° 135 CH3I +1 CH2CH2) 1 1 (012+2-CIPhl oil 11nd 4.72 (1,1) 11°136 CH2OHCM, HHCM2 (2-CIPhl oil, end 4.71+<1,181°137C)+3) IN CH2OHCI'+2+2.6JC112Ph) Oil, End 4.8 3 (d, 1M).

138 Hca3cu, C)+3 CM3 C’Bs α2(Phl”nd 4.65 (da+1.2H1゜M foot aO・C4,40+11,111゜ 139 B Cil, C13Cil, CF1301. CH2 (2-FFh) nd 4.65 (dJ, 2H).

MAs Shizuku-ss・C4,39+4.1141゜1.1s (i, 3111 Melting point '1o-52''C4, 42+?1.1)+1° Melting point 102-104・C4, 3911! ,1)11゜143)IC)I,CM3CM3CM,(:)l,Cl 12 + 2.6 JC Yu) zphl end 4.12 (s, 2) + 1゜144 HC1 l, CHI, el13Cil, CB, C11, +2.4-CF+, Pb l End 4.6 ++5◆d, 2H+.

Melting point 102-103'c 4.3G (11,11(+.

X4S C) I, M RCR, ellco C town 0 days 2fPh) nd' 4.64 (d, LI().

146 C) 13RM CI4. CR3CM, eMyo (2-FIPb) Oil , j-7t4.69 (d, lR1゜4.50 Td, XMl.

3.515d, Li41° 147 0, II l? CI(3ell, eR,C)+2(2,6-ffJ ,P! +1 oil, end 4.70 +71.1H1゜121 (ls116. 1H1 x4a cs, u g cH, C)+3cII3cu□(a-cxpbIfi &　4.72　+d,llI+.

4.52 +<1.1H1゜ 135 (wrapped, 3B) 14% +66.11).

3.34 (also 3) I) 3.34 +116.1) +1 145 (dd, 1111° C14(s*66.4111 xsx C) 13n) I 01. cy2cg3C1+201. cs2(z , b-(r), ph+ 1 dedication/do 4-7 (6,111P゜ 152 CM2C1, H) I Duck B HCH2 (Pbl Wax end 4.65f d, 1) 11° 153 C) M2C) + 3) 1) 1 cn3Fl m ci, +z−rph+? m End 4.7 fd, IH+.

154　o+2cH,a　Rcm3n　Bat2tz,5-(r+2ph+　a End 4. ) (+1.1!11゜3,) II (+!+1.1111゜ 3.19 (114,2) 11° 346 (s, 311+.

155 0!2C13M B CM, B II Cl12+2-1:XP&+ + Oil, end 4.75 +41++l.

C91 (1!, 1) 1).

3J　(671,1)11゜ 344 (ゎ1H).

3.25 Ti! d4dd, 2) 156 CH3CN, HHCH3) I II CM2f2.6-(C1), P bl end 4.112 fd, 1) + 1゜Kongdong Sfu7-fufu, S’C4, 69 (d, 1) 11° 157 C) I2CO, H) I C) I3R) I CB2 (2-(CB3)Pl+1 oil, end 4.115+<1.1) 11°151 1 CM, C14, RM C)l, RHCH2 (2-BrPbl oil, end 4. )X (d, 1jl+.

124 (*, 2 days) Table 13 ! 5G CM, B B C Town 14) I C) + 2 + Pbl “””’do 4 ．． 64 +4. lHl.

160 CH3) I N CMlM 11 012P (2-FPhl oil, en Do 4.7 ((1, IHl.

161 C1l, HB CR, RB CJI, l’(2J-ff+2Pk+ Oil, End 4.7 (d, LII+.

Table 14 4.06 (q, l舊).

3.34 (lN, 11++ Table 15 ILLI Oi, II II C112el131! ml ell, (2-( CM, l deh) oil, end also 55 (15411, 2H 3.35 (611, lH1 Table 16 169 RRen2cR, cm2co, C) + 2 (P) 11 C irises 2 (Ph) m End 4-6 (egg, 4 servings)

170 H)l el12C1l, C1l, CB, CM, 12JPhl C1l , +24Phl (end 4.70 (11,4BlB ! 71 11) I el12CB, C112CH, 01,012+2-rPh l? Mountain, End 4.71 (brs, 2Hl.

3.15 (s, 3H1 Base! A Barley (HordeuIllvul, gare), Golden millet (Echinoch) loa crusgalli), Bromus 5ecal inus),, Onamomi (Xanthium pensylvanicum) , corn (Zea mays), cotton (GossypiuIIlhirs) utum), Digitaria spp, ), Oenokoro Setaria faberi, Anagao (I pomoea sp) p,), rice (Orytdsativa), sorghum (Sorghum b) icolor), soybean (Glycine max), sugar beet (Be ta vulgaris), velvet leaf (Abutilon theo phrasti), wheat (Triticu aestivum), and Kara Avena fatua and Cyperus rotu ndus) are planted with tuber seeds and dissolved in a solvent that is harmless to the plants. The seeds were treated before germination with test chemicals. At the same time, these crop and weed species were also treated with post-emergence applications of test chemicals. For post-emergence treatment, plants should be 2-18 cm in height (kuni to trifoliate stage). Treated and untreated plants Controls were kept in the greenhouse for approximately 16 days, after which all varieties were compared to untreated controls. and visually evaluated. The plant response ratings summarized in Table A are 0 and 0. It is based on a scale of 10, where O is no effect and 10 is perfectly tuned. It is a clause. A dash (-) response means there are no test results.

Table A compound compound Image damage 11 (2000g/ha) 43 44 45 46 47 (iffl damage IQ (2000g/ha) 43 44 45 46 4l After germination Before germination Barley oooooo Barley oooo.

Dogfish oooooo Dogfish ozzo.

Suzume no chahiki oooooo Suzume no chahiki oooo.

Onamomi 30000 Onamomi oooo.

Corn 00000) Corn oooo.

Cotton oooooo Cotton oooo.

Kingfisher 300-3 Kingfisher 40002 Giant Elephant ooooo 52353 Morning Glory oooooo Morning Glory oooo.

Hamas f OO-Q O Hamas + J -00-0 rice oooooo rice oooo .

Sorghum oooooo Sorghum oooo.

Soybean oooooo soybean ooao.

Sugar beet oooooo Sugar beet oooo.

Velvet Leaf oooooo Velvet Leaf oooo.

Wheat oooooo Wheat oooo.

Oats oooooo Oats oooo.

Compound Damage collection (400g/ha) 1234567 B 91011121314!6 Suzume no Chiyahiki 000000000000030 off fir 2 X 2 1’ 4 10 3 2 3 2 1 2 0 Compound Morning harvest (400g/ha) 1 2 3 4 5 6 Fu 8 9: LO11 12131416 before germination Barley 030250020000000 Golden millet 1010 9 lO1090 :10 Fu 898807 Suzume no Chiyahiki 000063040023002 Onamomi 00003405000500-Corn 030364040 000002 Cotton (j OOO2,, OO30000000 Mehishiba 99) 99609 Fu 8 Fu 7030 Giant foxtail 9911996097 787205 Morning glory oooooooooooooooo

Hamas lfO00004020000000 rice ooooooooooooooo .

MoO: ffshi0 9 0 8 fu 0050000006 dog bean 0001600 32000000 sugar dai-+n 0 1 0 0 2 4 0 3 0 0 006252600 1 Wheat 000020030000000 Oats 00003200002 0000 ~ Rororororo 10 Roro OH Rororo O 唖 Rororo n Roro Ken Rororo 0 Rororo 0 mouth & I'I IocPoN Toro wryR1oo-cloto 0" 00 0+-1000 Rorororororororororo MO Rorororo 0 Rororo -〇F7110　+I　Orororo6　ro f　OONI　Q　P+-〇〇low 0 000〇〇Rororororororo= I/I O-low M-M? +-11N09 CI PI O Loli Lolo Lo Roro 0 Rorororo 0 Rororororo compound Damage (167168 after germination) (200g/ha) Shakumugi 00 Dogfish 12 Suzume no Chahiki 00 Giant foxtail grass 20 ~ Rorororororo FIPI000 Roro 0 Rororo - ○a Milo 00 Rororororo 0ro Q Roro OFl 660O Rororo 〇〇〇〇〇〇〇〇-〇〇〇〇 ++10o Rororo Ro-1 ~ Roro 111 1 Rolarororo■G Roro~~Rorolo compound Taji print damage 11 (200g/ha) 167 168 Giant foxtail 10 centre Sugar beet 40 Rororororororororo 10 Rorororororoto Rorororo 0 Rororo 0 Rorororo Lolo Io ooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo (10o + N Rororo 0 Rororo So o Roo Rororo 0 Rororo oo Rororo Q? 0rororororo Ro0 Roro eoooooo mouth ~ Roro omoo mouth Q Rororororororo O0a 0001 0 lololololol 0 lolo 0 bites. Mouth＠l　e　70　M Roro ~ Maloro 0 Rorororororoto Lolo O Lororo Q Roro 0 Lolo 0 Roro 0 Stimulated 0 Rororororo O Lororo 0C10 0O&l’l Q Pi Q PI O00 Rorororo Oel OOOO So 00 0 lololol 0 mouth 0-00 mouth. QoO-〇〇〇-〇〇〇〇 Rororo 0rooOro 01%I Roro 0 - Rororo 0 Roro Q Rororororo 0 - Roro Q - Rorororo OOO Roo 0 Roro.

1o OH ro 00 Roro Qro OH ro 00600 Hikari Be F He Roro 10 Roo Rororo 0 Rororo Qo Roroto 00000600000000 0OcP 00006000CIO0000000e OOONOOOOO oooooec+t-00eOeleC1106@000000000 Rolo O NQ Rororo OOOO Roro 0 mouth guard RoPa0060 Roro 0 Roro 0 Rororororo PI 　000m0elOOOO口oooooo.

No Roro OO Rororo 00o Rorororororo o+oe+-+ooooo Roro 0 elOOOO mouth @11 eoOm000c1000000000ro lololololol 0 mouth O mouth 0 Roro O Rororo compound Harvesting (50g/ha) 155 156 157158 166 16f xrs-6 pre-germination Barley 0000000 Dogfish 4062000 Sparrow tree ζki OOO0000 Onamomi 112 l oll Corn 0000000 Cotton 0030000 Mehishiba 0200000 Giant foxtail grass 2’080000 Morning glory ooooooo.

,,ysy　OOOO-000 @OOOO0000 Sorghum 2000000 Soybeans 1,000,000 Sugar beet ooooooo.

Beyabet Leaf 3222000 Wheat ooooooo.

Oats ooooooo.

~ Roro 00 Roro ~ -〇〇〇〇〇〇〇log QMrooOroCI NO000ro Rorororo Rooo-ro 0 Rorororo ate mouth O Rororo @1 0#Cll60ON OC36000 Roro 0% 06000elOOOOOOOOe)O Rororo* oeo o Rorororo O mouth ooooooo.

1 Roro oc+ooo Rorororo 00 Roro 000 豐 Roro 6C) Rorororo 0 Roro Qro Rorororo h Rororo Q Roro 0 Rororo ooooo Mouth Ox OOO00001:l OOOQOOCI OO-Roro 600 Roro el OO60 Rororororo 0 Rororo oo Roro 0 Rororo 000o06 To Ro 00 Roro N ◎ Roro 00 Roro Roro 100 0000~060000000 mouth m 0g1010()O+0+0roooooo oo Roro 00100 M M ONOG O0000a 0M01e+0Of0 0C10000 Roroso Rocho-Rorotoro OO00 mouth ν Roroto Rorororo 0 豐Roro IC36066DOIoooc111L10O Tohero CI O0000 Roro Roro 00 Roroto WOO Roo Roro COO Mouth FI O Roro O Rorororororororo O Rorororo O~ Rorororo 0 Rororo 6000 mouths Omcroooo mouth M N O10ooc+oo.

m ooooc+c+口0eOeOC100OO-roro0ro00rorororororoQ O Rorororo Lo chain Rorororo NI + Q Roro 0 mouth 0-Ro QCm RoQ 5 mouths, Rororo OOOOOOel　OOO-〇-Rororo Qro NO Roro 0 Rororo 00＞　o　F+ o Roro M x o Roro OM C1e, Rororo Ookaro Rororororororo O# 0000 mouth 1el O6060000 RoroOOOH20C )　60ψoooooooooo.

P OM OI Me low 000006000… Ro MO Rororo O so oo Zhan Roro O mouth oeN 000e600C) 000000 Roro Om+IC10606CI CI M mouth Ooo Rororo 661 oo Roro Oe OF’l OOOO6C) C I C16@P oooo・600000000 ao mouth P+ 00061: 1eellc) e100000000# 0OO06aOO Roro 060 Roro 00 Compound Harvesting (50g/ha) 155 156 157 158 166 167 168 before germination Barley 0000000 Dogfish 10 9 10 10 5 0 1 Sparrowtail OO2,00 00 Giant foxtail grass 9999522 Morning glory ooooooo.

Hamasuge ooooo-o.

Wheat ooooooo.

Oats ooooooo.

Exam B Barley (Hordeum vu1gar'e), Golden millet (Echinochl) oa crusgalli), black grass (Alopecurus myo) suroides), Bromus 5ecalinus ), Stellaria media, Xant hium pensylvanjcum), corn (Zea mays) ), cotton (Gossypium hirsutum), crabgrass (Digit aria spp, ), Yaemugura (Galium aparjne), O Setaria faberi, Chenopo dium album), morning glory (I pomoea spp,), Brassica napus, rice (Oryza 5ativa) , Sorghum (S orghumbicolor), Soybean (Glycine) wax), sugar beet (Beta vulgarj, s), velvet Leaf (Abutilon theophrasti), wheat (Tritic) uaestivum), Wild Pack Wheat (Polygonum co. nvolvulus), as well as oat (Avena fatua) and Plant seeds of Cyperus rotundos tubers and plant treated before germination with a test chemical dissolved in a solvent that is non-toxic to . At the same time, these crop and weed species were also treated with a post-emergence application of the test chemicals. . For post-emergence treatment, plants should be grown between 2-18 cm (2-18 cm tall - to four-leaf stage). there were. Treated plants and untreated controls are kept in a greenhouse for about 15-20 days; All varieties were then compared to untreated controls and visually evaluated.

The plant response ratings summarized in Table B are based on a scale of 0 to 10. , where O has no effect (and lO is full regulation. Dash (-) response means there are no test results.

Table B compound compound M Harvest (400g/ha) 169 1 fl O (fl Harvest (400a/ha) 1 69 170 Before germination After germination Barley 0 0 Barley 00 Dogfish 00 Dogfish 00 Black Glass 0 0 7, Ratsukagurayu 0.

Sparrow 0 0 Sparrow 0 0 Miminagusa 0 0 Mimi Nagusa 00 Onamomi 1 1 Onamomi 00 Corn 00) Corn 00 Cotton 1 0 Cotton O.

Mehishiba 10 Mehishiba 20 Yaemugura 00 Yaemugura 00 Oenocologa 0 0 Oenocologa lO Shiroza 3 0 Shiroza O.

Morning glory 1 0 Morning glory 00 2.7 seconds 0 0 2.7 seconds r OO rape 0 0 rape OO Rice 10 Rice O.

Sorghum 2 0 Sorghum OO Kara 7”gi 0 0 oat 00 compound Usage rate (200g/ha) 162163164165171゛After germination is 0000fu Dogfish　o　Oo　o　l.

Miminagusa 02005 Onamomi 2000B Corn 00009 Cotton 00002 Mehishiba 00009 Yaeegura 00002 Great Elephant 00009 Okiza 00002 Morning glory 00002 Hamas r O0009 Brassica ooooos Rice 00009 Sorghum ooooos Asahi oooooo Sugar beet 46225 Velvet leaf oooooo Wheat 0000B Wild > tonkwit OO. . 4 Oats 00004 Compound Harm collection (200g/ha) 162 163 164 165 171 before germination Barley 20030 Dogfish 100010 Black Glass 3:13210 Sparrow Chiyahiki 222010 Miminagusa 2601C) 10 Onamomi 000-5 Corn 10007 Cotton 00007 Mehishiba 20009 Yaemugura 000010 Giant foxtail grass 33209 Shiroza 02-010 Morning glory 00004 Hamasuge oooooo.

Brassica 02007 Rice 00005 Sorghum 00001 dog bean ooooos Sugar beet 03229 Velvet leaf oooos Wheat 00201 Wild Beck Wheat OO021゜Oat 20229 compound compound 169 170 169 170 100Q/ha □69 170 compounds Usage rate (50g/ha) 162163164165171 after germination Barley oooo.

Dogfish 00009 Black glass oooo.

Sparrow 00001 Miminagusa ooooo.

Onamomi 00004 Corn 00007 Cotton 00002 Mehishiba 00005 Yaemugura ooooo.

Great Elephant 00005 Shiroza oooo.

Morning glory 00002 Hamas f 00002 Brassica oooo.

Rice 00009 Sorghum 00002 Soybean 00004 Sugar beet 23220 Velvet leaf 00005 Wheat ooooo.

Wild Beck Wheat oooo.

Oats ooooo.

Compound 1 x installation (50g/ha) 162 163 164 165 171 Karasumu Gi　oooo.

Exam C Barley (Hordeum vulgare), Golden millet (Echinochlo) a crusgalli), black grass (Alopecurus myos) uroides), S tellaria media, Namomi (Xantium pensylvanicum), corn (Z eaIllayS), cotton (Gossypium hirsutum), meshi Digitaliaspp, Bromus tect arum), Setaria faberi, Gree Foxtail (Setaria viridis), Datura viridis (Datura stramonium), Johnson grass (Sorghu m halepense), n oza (Chenopodium album) , morning glory (I pomcea spp, ), brassica (Brassic a napus), rice (Oryza 5ativa), sicklebod (Ca napus), rice (Oryza 5ativa), ssia obtusifolia), soybean (Glycine max), Beta vulgaris, teaweed (Sida) 5pinosa), velvet leaf (Abutilon theophras) ti), wheat (Tri ticuaestivum), wild packweed Eat (Polygonum convolvulus) and oat (Avena fatua) and Ha'7 sedge (Cyperus rotund) US) tuber seeds are planted and dissolved in a solvent that is harmless to the plants. Treated with test chemicals prior to germination. At the same time, these crop and weed species It was also treated with a post-emergence application of test chemicals. For post-emergence treatment, plants should be grown at 2.18c. The height ranged from 1 m to 3-lobed stage). Treated plants and untreated vs. The plants were kept in the greenhouse for about 24 days, after which all varieties were compared to untreated controls. , and visually evaluated. Plant response ratings summarized in Table C range from 0 to It is based on a scale of 10, where 0 is no effect and 10 is full adjustment. It is. A dash (-) response means there are no test results.

Table C compound compound Usage book 1 x (500g/ha) 323493 Usage damage x 1 (500g/ha) 323493 Blank Glass 004 Black Glass 951O Mimina Guna 000 Mimina long length 406 Yu) Tosemi 0 0 3 Elbow fir 0-9 Dowie Blohm 004 Doweets Blohm 400 Oenocologna 757 O Oenokolog length 10 10 1.0 Green foxtail 5 o o o Green Foxtail 101010 Chimney 070 Chou Morning Glory 000 Jeongsing Grass 300 Jeongsing Grass 1010 9 Shiroza 5 -- Shiroza -- -- Morning glory 000 Morning glory 000 Hamas R 033 Hamasuge 003 Sickle Bod 0-〇〇 Sickle Bod 0--Fat 000 Soybean 00 0 Sugar beet 053 Sugar beet o o 5teeweed 00 Fu Tei Weed 3 5 6-Kunkutsu Toleaf Fu 6 4-Lere Torif 6 3 4 Wheat OOS Wheat OOS Wild''/Gutsukuweet 860 Wildtonokusokuweet Oo8 Kara Sumgi 030 Oat 406 compound Kuji Interest Fee (25 (, g/ha) 22532349394102111112 0130131132133134135 compound fl harm pick up (250q/hal 2253234 93 94 1021181 20130131 D2 1] 3’l14 135 Dogbi” 10101010 1010 10 10 lO101010101010 Black Glass 710 8597 6 710 7 B 7 610 6 Miminaku i left 062064 9 7 fu 88789921 ft to mi 0 fu 00 fu 103436010 ft 30 ft Corn 233080 21010 4 6 S 3 8 0 Cotton 0000 03 0 3 9 5 0 2 3 4 0 Mehish” 8 9 2 8 910 10 10 10 10 lO10101010 Dowie Blohm 0220 04 3 S 5 4 5 6 4 I+ 3 Giant foxtail zo xo xo xo lo xo lo xo 10 10 zo lo 1o lOx .

Green Foxtail 10 9101010 9 Fu 10 10 10 10 10 10 10 10 Japanese morning glory 060003 3 0 4 5 S 5 5 6 0 Jiyoung Glass 81087116 41010 91010 7 s8 Shiroza 310---610 9 9 9 9 1 110 9 Morning Glory 01000043---53550 Hamasuge 00000 5 0 4 5 4 4 4 8 5 0 Afukuka 232000 0 2 0 0 0 0 0 2 3 rice oooo-a ko 3 9076 3 30shi Tsukupatsudo 0303 Fu 3 3 9 Fu 5 8 Fu Fu Fu 8, ni further l OOOOOOOOfu 6343665 Sugar beet 040000 6 9 6 5 Fu 8 Fu 96 Teeweed 09252 Fu 36986 Fu Fu 5 10-9 Shikto Leaf 305328 0 9 9 9 Fu Fu 5 7 7 Wheat 000053 4 2 - 4 2 4 4 6 0 Wild 5 Kutsuku Wheat 050060 Fu 99101110 Fu Fu 8 Oats 032024 3 6 4 2 3 4 0 6 0 compound (i1 Harvest (125g/ha) 225323494102118119120 130131132133134135 compound Equipment collection (125g/hal 22532349394 102118 119 120130131132133 134 135 Dogfish 10101010 10 XO10101010101010101010 Black Glass 310 6373 3 6 410 4 7 7 3 7 3 Miminaku”?030043 ．． 3 hehehehe 8) m197 elbow fir 000005043050107. -0 toe Sorghum 02302005310325030 Cotton 000002 0 3 3 5 5 0 0 0 3 0 Mechishino 82fu 2389fu 10101o10xo 10xoso10 Dowie Blohm 000003 2 5 7 4 3 3 4 3 S O Oenocolog length 910 8101010 II 10 10 10 10 10 10 10 10 10 Green Foxtail 16 F1O106S 10 10 10 10 10 10 9 10 lOchi Seven noasagao mouth 0000 0 0 0 3 2 5 5 4 6 0 shoa Song Grass 5 Fu 1755 210 810 8g0 9 S 7 Fu 0 The 23---- 5 3 9 9 0 8 ml 8 Fu Morning Glory 06 0004 0 - 4 + -33340 Tsuma Mask - 000003033S O43300 Brassica 000000 0 0 0 0 0 0 0 0 0 2 rice 000030 0 2 7 + 0 6 5 3 0 0 Shikurubotsudo 0000-0 0 S 41 S S 6 6 5 Fu 3 short 000000 0 S 3 5 0 4 0 Kazu 5 0 Sugar beet 030000 3 7 6 5 4 6 6 6 7 6 Teeweed 050206 0 - 3 9 6 5 7 6 3 3 Velvet Leaf 2010 Mouth 0 @ 68567466 Wheat 000032 3 0 Fu 5403240 Wheat /”,’Cry) 0000 Ko 059819 Fu 8 7 Fu Caras Wheat 0 0 0 0 0 3 0 0 6 2 0 3 3 0 4 0 Compound 1 month harvest (62g/ha) 3234 94 102 1181201301 31132133 134 135 Inubi” 0300910055376 Bra Tsukugrass 000 0 0 4 0 0 2 0 3 0 Miminagusa 000 0 0 3 3 3 0 0 3 0 elbow fir ooo -o o o + o o　o　-Corn　ooo　-o　o　o　o　o　o　o　.

Cotton Goo OOOOOOOO200 Mehi%’000007000003 DOWIE BLOME ooo o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o so so so so so so so such.

Oenoco 0g length 0000510033354 Green Foxtail o oo　o　s　s　o　o　o　o　o　.

Datura morning glory 000 0 0 0 0 0 0 0 3 0 Jiyeonseong Glass ooo o o o s o o o o o z.

Shiroza 00- 0 0 8 2 4 0 0 0 4 Morning glory Goo OO OOOOO30 Hamasuge Goo OOOOOOOOO3377 minutes o o o o o o o　o　o　o　o　o　o　.

Rice 000 0 0 6 0 0 0 0 4 0 Shikuruhot oo-o o　o　o　o　o　o　o　.

Soybean Goo OO2000000 Sugar dace: yy 0003000303 Ko 3 Teeweed 000 0 0 2 0 0 0 0 0 0-ν Shikto Leaf 300 0 0 5 0 0 0 0 3 3 wheat ooo o o o o o o o o o o o o o.

Wild 5ζ Tsukweet 000 0 9 2 6 3 5 3 4.

Oats ooo o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o.

Compound 1 damage 1 + 62 g/ha) 22532 3493 94 1021181B 120130131 xf2133 xi4 1] 5 Inubi" II 10 10 10 lo fu 9 10 10 10 yu 0 10 10 fu 10 10 Blank Glass 072 Ko 00 3 5 S 7 3 S 7 0 5 0 mimina? One F 000000 0 2 Fu 6 Fu 8 7 Fu 9 6 May 1 fir oooo-xo 4 oo-o’ss-.

Corn oooooo OOO2002030 Cotton 000000 0 3 0 S OOOO30 osoooos' 410101010 91 0 9 9 g Dow Loom 000000 0 0 5 3 2 0 2 2 3 0 Giant foxtail grass 1Ofu 2 4 7 10 9 10 10 ml 10 fluff 9 green foxtail 56 fluff 2 4 5 10 10 10 10 10 10 5 10 9 Chiyousenoasaga O 030000 0 0 0 2 2 4 5 3 5 0 Jiyeonson Glass 252400 0 Fufu 6 3 Fufu Kazu 74 Shiroza 0011-- - 3 0 9 B Ofu 7 7 7 Morning Glory 000004 0 - 4 + -33030 Y mask' -000000330040000'5 -)-0000000000000000 rice ooooooo o o S 8 0 0 3 2 0 0 000060 0 2 6 3 2 5 6 5 7 0 Teeweed 0502-6 0 -) II 3 4 6 4 3 3-enrento 7-00000 0 8 6 7 4 0 3 3 S 4 Wheat 000000 0 0 4 3 0 0 2 0 3 0 Wild〉kutsukrai-)000000　3　5　7　1　4　7　fu　S　fu 5 Karakagi ooooooo OO400020 O compound Morning harvest (31g/hal 94 102 1111 120130131 13 2 133 134 135 After germination Barley ooooooooo.

Dogfish 004i0033064 Black glass ooooooooooo.

Mimi Nagna ooooooooooo.

Elbow fir o-oooooooo- Corn ooooooooooo.

Cotton ooooooooooo.

Mehi'//' OOOOOOOOOOOO Dowie Blohm ooooooooooo.

Oenocolog t oozsoooo 4 3 Green Foxtail 00 03 million morning glory 0000000000 - 0-2-30000 Morning glory 0000000030 i,? ) f　OOOOOOOOOOOO0 77 minutes 0000000000 Rice 0000000030 Shitsukuru 2tsudo 0000000000 soybeans 0000000000 Sugar beet 0000000030 Teaweed 0002000000 29 Cut Leaf 00G000003m Wheat 0000000000 'Fee#)'/<7ri'Fee) o o 6 '0 3 0 4 0 4 0 Kara, gi 0000000000 Compound Usage rate (31g/ha) 2259410211g! 191201301 3113213313'4-135 before germination Barley ooo o o o z o o o o O23゜Inubee' 3105 41 01010 41010 510 77' Rack Gray" 000 0 4 3 4 (143040 mimina l"f ooooo) 6 6 fu 695 Me) To [Mi] O-00000-033-0 Corn ooo o o o o o　o　o　o　o　o　.

Cotton 000 0 0 0 4 0 0 0 0 0 0 Oenocologna 29 356511026) 5a Fu Green Foxtail 363499 625.1145 Fuchousen Morning Glory 030 0 0 0 0 0 1 040 Jiyeonson Glass 050 0 S 4 4 0 4 F 3 5 3 S 0 the 00- 3 0 9 0 0 S 7 7 S 6 Morning glory 004 0 - 3 + + 0 3 0 0 0 Hamas f ooooooooo 4 oo o.

Sicklebod Goo O2430550S O soybean 00G 0 0 0 0 0 0 0 2 0 0 Sugar beet 00002340.45 Kazu 6 4 Tee Weed 056 0 5 3 6 2 3 6 0 0 0 Velvet Kanofu 000 0 2 5 3 0 0 0 2 4 3 Wheat Goo OO3 0000030 Wild 5 (Tsukweet Goo 2 - 6 6 3 6 6 5) 3 Oat 000 0 0 3 0 0 0 0 0 0 Q test The compounds evaluated in this test were formulated in a solvent that is harmless to plants and Apply to the soil surface before the seedlings germinate (pre-emergence application), and to the water covering the soil surface (application suitable for paddy fields). (post-emergence application), to plants at the mid- to four-leaf stage (post-emergence application). germination Sandy loam soil was used for pre- and post-emergence tests, whereas silt loam soil was used for paddy field tests. Mud soil was used. The depth of water is approximately 2.5 cm for rice field tests, and during the test period This level was maintained throughout the period.

The plant species in the pre-emergence and post-emergence tests were barley (Hordeum vulga re), black grass (ALopecurus myosuroides) , S tellaria media, corn (Zea) ways), cotton (Gossypium hirsutum), crabgrass (D) 1g1taria spp, ), Dowie Blohm (B romus tec toruIQ), Yaemugura (Galium aparine), Oenokoro Setaria faberi, Setaria vi Chenopodium albuoi), Chenopodium albuoi, Morning Glory (Chenopodium albuoi), I pomoea spp, ), Amaranthus ret roflexus), brassica (Brassica napus), rat worm Lolium multiflorum, Sorghum b icolor), soybean (Glycine wax), speedwell (Ve roica persica), sugar beet (Beta vulgari) s), velvet leaf (Abutilon theophrasti), Wheat (Triticu aestivum), Wildback Rye) (P oligonum convolvulus), and oat (Aven It consisted of a fatua). All plant species were treated with the compound for the pre-emergence portion of this test. Planted one day before application. Planting these seeds is suitable for the post-emergence portion of the test. adjusted to produce plants with The plant species used in the paddy field experiment were golden millet ( Echinochloa crusgalli), rice (Oryza 5ati) va) and Cyperus difformis there was.

All plant species were grown using conventional greenhouse methods. compared to untreated control Visual assessment of damage appearing on treated plants at approximately 14-20 hours after application of test compound. Recorded over a period of days. Plant response ratings summarized in the table range from 0 to 10. scale, where O is no damage and 10 is plant death. Ru. A dash (-) response means there are no test results.

appearance Compound Rice 225689 Fu 0 4 0 Black Glass 5094998585 Mimina Guna 9040988896 Corn 2223117 7 360 Cotton 00003:10333 Mehishi/Ku 8 3 Fu 8 8 Fu 9 3 6 6 Douwi Brom 00 02786050 Yaem Graph 52086 Fu 2 4 4 Ohkonokolog Length Fu 6 8 8 7 8 8 Fu B Fenokorobuna 90008965 86 Morning glory 030:1202000 Aobie 20007 Fu 6005 Afrana 5000000302 Rat wheat 4376B980 Fu 0 Sorghum 3034686060 Soybean 0000662227 Speedwell 90009109796 Sugar beet 8 0 0 010 10 8 9 910-Gong/Kutto Kanofu 53246 Fu 6 6 Kazu 5 Wheat 3446B-7040 Wild 5 Kutsukweet 95601010999 Fukara Mugi 0003 866450 Compound 6th and moon damage! )’ (250q/ha) 136 145 146 14f 1 52 153 154 155 157 158 Misseda Golden millet 9 9 8 8 10 10 10 10 lO1O1i'ii6 Fufu 7999g197 Tamagayatsuri 948810910999 compound Hair removal 1st damage (250g/ha) 136 14S 146 147]-' , 153 154 155 15f 158 before germination 33245 fu 5 3 3 0 Black Glass s zo xo 10 1o 10 lo fu 9 Fumimina Kika 7 7 7 899889B Corn 432356 Fu oo.

Cotton 0323554232 Mehishiba 1o 9 1o 1o xo 10 10 1o 10 x.

Douwi Blohm 3300567043 Yaemugura - 300---6 Oenocologna 10 10 10 10 10 10 10 10 10 10 Enocorodate 91010-998998 Morning Glory 0202000000 Aobie 7302g8fufu 77af’5f-5000060433 Rat wheat fu 10 10 10 no lO10375 sorghum 5348 10106463 Dog beans 3102 fu 80000 Speed radish---981078 Fusato radish 9600989! Il l　F^-nkut Kanofu　6　fu　5　fu　8　8　8　e　fu　8 wheat 43 34555040 Wild Tsukweet 9554998 Fu 86 Oat 44031 0106-00 compound fl Harvest (125g/ha) 136 145 146 147 152 1 53 154 155 15f 158 after germination Barley 0025546040 Black Glass 402-8663 Fu O Mimina Agency 9 0 0 0 Fu s 5 Fu 2 Tofu Morokoshi OOO2666060 Cotton 000022 0002 Mehishinoku 6 0 3 Fu 4 5 Fu 0 3 4 Dweeb o-mu OOO O555040 Yaemugura 4000336230 2 total 2 Toenokorok 2ji f5547 Fufufu 4fufuenocologna 6000fu 66-75 Morning Glory 0002000000 Aobie 2000353005 Abuchina 5oooooooooo.

Rat wheat 0056477040 Sorghum 2003332000 Inugame 0000430003 Nuvidwell 7000698 Fu 94 Sugar beet 200084-6 60＾Go/Kuttoori 7 5203355503 Wheat 0325366040 Wild 5 (Tsukuito 9040.896350 Oat 000035 3030 Compound (E1 month damage 1 (125g/ha) 136 145 146 147 Yu 5 2 153 154 155 15fu 158 Paddy field Dogfish 9 6 6 6 10 10 10 10 10 10 7 34 7889 day 2 Targa cyperus 934499th order 98 compounds 1x installation (125g/ha) 136145146 147 152153 1 54 155157158 Before germination Barley 2003543020 Black glass 6fu a xo 10fu 6JI4 mm long length 7 7 6 7 9881+118 corn 1102323000 Cotton 02120:13020 Mebishiba 10 9 10 XO101010101010 Dowee Form 2000345030 Yaemugura - 0 0 0 - - Fu -00 Oh Enocologusa 10 9 10 9 10 10 10 10 10 10 Eno Cologna 81010-99891!18 Morning glory 0002000000 Aobi! 7 2 0 0 7 7 6 6 3 677’5f 5 0 0 0 0 3 0 3 0 2 rat wheat fu 7510568050 sorghum 412110103330 Soybean 0000460000 Speedwell 7----8886 F 6 Sugar beet 95008 F 8 8 6 6 Berkut Kanofu 7 3 5 5 Fu 8 8 Fu 66 Wheat 3003444030 Wild) Kutsuku Wheat 934388 Fu 6 7 4 Oats 0 023103-00 compound snout Barley 0004423020 Black glass 4000544020 Mimina long length 2000766.050 Corn 0000324000 Cotton 0000020002 Mehishiba 2020 3 36032 Dowielow Buddha 0 0' OO403030 Yaemgra 0000025 00- O 1st No. 0 Guna 203246 Fu 043 Enoko 0 Guna 30005454 -4 Morning glory ooooooooooo.

Aobiyu 0000040003 Affuna oooooooooo.

Mouse wheat 0004304040 Sorghum 0002001000 Inugame 0000220002 Speedwell 0000668480 Sugar beet 0000G-5230 Velvet Kanofu 2000343300 Wheat 0003345010 Wild〉Kutsukweet 4000-96040 Oat 0000022 000 Compound Installation collection (62g/ha) 1) 6 145 146 14fu 152 153 154 155 15fu 158 Ketta Dogfish 9 4 5 410101010 910#7A 41137883 60 Tamagayatsuri 9222999 1 1 compound 1st instar (62g/ha) xxrs x4s 146 x4fu 152 153 154 155 15f 158 before germination Barley 0000332000 Black Grass F 3 3 6 F 6 4 6 0 Mimi Nagna 5 6 6 1 9 8 Fufu 7 Fu corn ooooooooooo.

Cotton 0000002000 Mehishiba 10 9 9 10 10 10 10 10 9 9 Taweeb o -muOOOOOO33030 Yaemugura 5ooo-o 3 oo.

Oenocolog length 10 8 8 8 10 10 10 10 10 10 Nocologna 5 10 10 - 7 98785a) - 恍PO oooooooo oo.

Aobiyu 6000665304 Afghanistan 2000000000 Mouse wheat 4307465030 Sorghum 2000632000 Dog beans 0000230000 Speedwell 2---158 7 6 6 5 Sugar beet B5007 66665＾υShit Leaf 522556 Fu 3 4 3 Wheat 0000 333000 Wild''/Kutsukweet 83307 Fu 6 4 4 3 Oat 2 000000000 Compound Morning Harvest (3, g/hal 136145146147152153 154 1 55 ls) 158 after germination Barley 0000003000 Black Glass 30000000-0 Mimina Guna 0000023000 Corn 0000002000 Cotton 0000000002 Mehishino<0000223030 Dow Brohm 0000002000 Yaemugura 0000000000 Great Enocologna 0000044030 Enocologna 0000030400 Morning glory 0000000000 Aobie 0000030000 Abu juice 00G0000000 Mouse wheat 0000000000 Speedwell 0000034000 Sugar beet 0000-00200 ^Gong/Kuto Leaf 2000200000 Wheat 0002020000 Wild backkwit oooo 6 o-oo.

Oat 0000000000 Compound f 152 g/ha) 36 □, 5 46 □, 152 5 3 □5. □55　□5□　、58peda Dogfish 634399101099 gi 2011424220 Tamagayatsuri 700099-,--2 compound Morning Harvest (31g/hal! 36 14514614) 152 Is Go! 54 155157 158 before germination Barley ooooooooo.

Black Glass 5003563330 Mi Minaku Nine-4 3 5 Fufu B Fu 5 7 3 Tomo O Co-70000000000 Cotton ooooooooooo.

Mehishi/Ku 8 9 9 10 10 10 5 8 5 Dow Low Muoooooooooo.

Yaemugura 5ooo-oooo.

Giant Enoco Ogusa 8 4 6 Fu 101010910B Enocologna 01 010--35583 Morning glory ooooooooooo.

Aobiyu 4000530000 Afrana ooooooooooo.

Mouse wheat 0003333000 Sorghum 0000320000 Fat beans 0000200000 Speedwell 2---666463 Sugar beet 00065442 4ba υshukut leaf 3220304030 wheat ooooooooooo.

Wild 5<Tsukuwit 5000664320 Oat Oooooooo oo.

Compound Trusted interests 11 (16g/ha) 145 146 14fu 152 153 1 54 155 157 15B After germination Barley 000002000 Black glass ooooooooo.

Mimi Nagna ooooooooo.

Corn ooooooooo.

Cotton 000000002 Mehishino<000000000 Douwi Forest 00000000 Yaemgra 000000000 Enokorogna 000030000 Enokorogna 000000000 Morning glory 000000000 Aobie 000000000 Afrana 000000000 Mouse wheat 000000000 Mo. -1shi 000000000 Dog beans 000000000 Speedwell 000002000 Sugar beet 0000000-0 Be, Shikut Leaf 000000000 Wheat 000000000 Wildback, Yi) 0 0 0 0 0 5 0 - 0 Oat 0 00000000 Compound Asaharu Shoji ixs g/ha) l 5146 Yu 47 152 153 154 155 157 158 Beta Dogfish 023988989 Fall 0° 1212000 Tamagayatsuri ooo------ Compound Equipment 1 x (16g/ha) 145146 x4i 152153154 15 5157 158 before germination Barley 000000000 Flak f5 0 0 0 3 3 3 30 0 cotton 000000000 Mehime 47510g8634 Dowie Forest 000000000 Yaemgra 000-cioo'o.

Giant foxtail length 2 2 2 111010 610 5 giant foxtail 10 10 - 0 0 3 3 3 0 Morning glory 000000000 Aobie 000400000 Burapu-000000000 Mouse wheat 000000000 Mo. -Ishi　o　o　o　o　o　o　o　o　.

Soybean 000000000 Speed Ugo J----554 3゜ Sugar beet 0003333 . 3-5 Cut Leaf 020000000 Wheat 0 0 0 0 0 0 0 0 0 Wild Z-; Tsukuwit 00043300.

Oat 00000000G Exam E A plastic container was partially filled with Nlutrom soil. Then saturate the soil with water Ta. Indica and/or Japonica rice (Oryz a 5ativa) seedlings, Echinoch Loa crusgall i), Bull Run, :L (Scirpus mucronatus), Dat Kusalada (L), and Cypera (Cyperus difforfflis) seeds, and Kwai (S ag fttaria spp, ) and water chestnut (E1eoch Tubers of ari'+ spp, ) were planted in this soil. A few days after planting , the water level was raised 3 cm above the soil surface and remained at this level during the test. Ta. The chemical treatment is formulated in a solvent that is harmless to plants and is added directly to rice field water. applied. Treated plants and untreated controls were kept in the greenhouse for 21 days; All treated plants were compared to untreated controls and visually evaluated.

The plant response ratings summarized in Table E are based on a scale of O to 10. , where O is no effect and 10 is full regulation. Dash (-) response means there are no test results.

0 16 el OOOOOOOL m OOQ C1-roe l OOOO60 0a l h OO660cm l el l + O 豐h OOa I CI 6 00? P.

h l a stirrup 0 6 # 6 0 N l 51 @P el D # ro .

+a + m l + Ill 00 Rocy +e +eo Toro. 0 mouths tn CI OCI O? -17'l Oy+ in 6000 e 0 mouths.

〜 −−m　M　+−1+−1m ψ　Makuguchi Q-1 draw　・　C U ■ Thunder 0 mouth. -t'h z r-1# r-o Mi 1 3-to glance O~: “-〇〇I OI OOO Exam F Barley (Hordeum vulgare), black grass (A 1 opec urus myosuroides), nightshade (Solanum n. igrum), Poaannua, Golden millet (Bro LIus 5ecalinus), Bromus tec torum), field penis cress (Thlaspi arvense), Field Violet (Viola arvensis), Yaemura (Ga liumaparine), Setaria viri dis), Ivy Leaf Speedwell (Veronica hedera) efolia), jointed goat Geras (Aegilops cyli) ndrica), Kochia (Kochia 5 coparia), Shiroza (C henopo+Hum album), Persian Speedwell (Vero nicapersica), Brassica napus (Brassica napus), Salsola kali, Lolium multiflorum), Shikagiku (Matricaria 1nodo) ra), sugar beet (Beta vulgaris), blackberry (Tr iticum aestivum), Wild Pack Light (Polygo num convolvulus) and oat (Avena fatua) ) and the test chemical is dissolved in a solvent that is harmless to the plants. The seeds were treated before germination using At the same time, these crop and weed species are tested with chemicals. It was also treated with a post-emergence application of quality. For post-emergence treatment, plants should be 2-24 cm tall. It was within the range. Blackgrass and oats are treated in the second growth stage after germination did. The first growth stage (1) was a - to two-leaf stage, while the second stage (2) was a four-leaf stage. It was in the leaf stage. Treated plants and untreated controls were kept in the greenhouse for approximately 21 days. Ta. All varieties were compared to untreated controls and visually assessed for damage. Ta. The plant response ratings summarized in Table F are based on a scale of 0 to 10. where O is no effect and 10 is full regulation. Dash (=) A response means there are no test results.

Table F compound compound Installation collection (500g/ha) j! s ωSeptember old book collection (500g/ha) 25f i9+z)″su1/X’ Field Violet 2 Fuplet) Iole Soto 2 Yaemugura 5 Yaemugura 0 Midori 1 Noenocologna 10 Midori 1 no″0 Kusa 4 Ivy 1 Norf Speed Ukoshire 2 Ivy Leaf Spi Douyuru 0 Joinbushi'Toko=Togeras 3-8' Compound compound compound Buchi'Kugu 5y, (1) o-y rack graph 27゛ rank Dallas (2) 0 S, f, -t,.

Night "Ndo 0 Kanno Kata, La."

Kui 9'to''zu4''　0　fei=itofuio〃to〃〃fi7b)>qo”to 0 2 Kera 02' La 0 Mido 1 Noenoyo. Keller,.

Mido "Anal Noa ° Riichika 7 (e-IJ-7, 2 Yosato, Wu 9.

Ivy Leaf Speed Uyuno 0. 2yoi, Kera)”:r” Tokura, t ,.

Join Tesodoco Togeras 0 Kotia 0 Kotia 0 Shiroza 1 Shiroza 0 Bell/Janos T-Dounil 2 Shikagiku 0 Sugar beet 3 Sugar beet l / Tomato (spring), Wild Benokuwheat 0 Oat 0 compound proboscis compound Morning pick-up (64g/ha) 25 (ffl Harm pick-up (64g/ha) 25 black Glass (1) 0 Black Graph.

Black Glass (2) 0 Nightshade 0 Nightshade 0 Nusunno Katabira 5 Nusunnoki Tabira 0 Iaji 3 Dogfish 0 Dawweeb leaf 0 Dowiefeom O Field-Tachirires 0 Fee/L/To ″″″O Off Eel Toshi CL 1/NT 0 Field''/Iolet Mouth Yaemugura 0 Yaemugura O Midorienokoroguna 8 Midorienokoroguna 0 7-f Bili -F Speed Well 0 Ivy Leaf Speed Uyunre 0 Ji'yoinf Nodoko Togerasu 0 Joy/Tesodoko Togerasu 0 Kotea 0 Kotia 0 Shiroza 0 Nroza 0 Batv7 Yankin Towell 〇-Urenxin Q-ko-Douyul 0 Fu-7'-) f-0 Fu-7゛Uzu1 0 Mouth・nrrn'〃、Nunre 0ro Ratsu-/'Ntsun Qshi 0, Nesumi LJ (7 Buminoshi Shizuku" nyafri).

Shikagiku 0 Sugar beet 2 Satoto icon 0 / Tomato (spring) 0 Wheat (spring) 1, Wheat (beans) 0- l Tomato (winter) o Wile l-〉ζTsukuweed 0 Wilde Tobanokuwie 1- 0 Oat.

Category ρgi (1) 0 Color calendar (2) 0 compound compound Exam G Alfalfa (Medicago 5ativa), Golden millet (Echi nochl, oacrus galli), Bermuda grass (Cynodo n dacty], on), broadleaf signal grass (Brachia ria plantaginea), field bindweed (Convo lvulus arvensis), Guinea grass (Pajcum maximum) um), Johnson grass (Sorghum halepense), Mexican D i gitariasanguinalisu, Bitted Morning Glory (r. pomoea 1acunosa), Cyperu s rotundus), birth lane (P ortulaca olerac) ea), ragweed (Ambrosia artemisiifolia) , Sandbar (Cenchrusechinatus), Smooth Crab Gras Djgitaria ischaemum, Texas bunicum (Pan) icum texanum), Tropical Kuju (Pueraria jav) anjca), and Cyperus esculentu Planting the seeds, rhizomes or tubers of s) in greenhouse containers containing greenhouse cultivation medium. I got it.

Each container contained only one plant species. The test compound is harmless to plants. Dissolved in a solvent and applied to the soil surface (pre-emergence). These applications are planted was carried out within one day. Control vessels without test treatment and treated vessels were kept under greenhouse conditions for 13-21 days after herbicide application. The growth of treated plants is Comparisons were made to treatment controls and visually evaluated. summarized in Table G The plant response assessment is based on a scale of 0 to 10, where O is no damage. and 10 is plant death. Dash C-) Response is no test result It means.

Table G Compound Rōjiki (250g/ha) 118 132 136 147 153 154 157 before germination Alfalfa 2530243 Dogfish 10 10 10 10 10 IQ 10 no ζ-Mikota 3-nu Su, 10, 10, 10, 10, 10, 10, 10, 10 No. 10 10 10 10 10y Feep Red Bin 10y Do 0510110 Guinea Grass No. 10 9 10 10 10 10, Shore 77 Class 8 10 2 2 10 3.0 10 Mejishibe 9 lOl OIOlo lo 1゜bi5pecht1□-Yunkur Lotori-0321032 ,,i-10101071038 ,,,,771081997 Lagout - 16205109 Santo bar -10-+-- yw-, cl rough 75t, 10 10 10 10 10 10 10,,, ,,,=,, 6 10 5 9 10 10 9t, pip, y, ;= 6 10 9 7 9 9 9 key ozyz2r 6 10 2 0 8 2 1 Compound Kiiro/Wasuke 1400110 Compound Before germination Ayafayafa 0310021 Dogfish 10 10 8 0 10 10 10 no (-Mini H-Douglas 9 10 1 10 10 10 10) b-to 1 Nofu Cyclitare Glass 21 0429109 Hui Pretobi/Dweed 0200210 Guinea Grass 9 91019910 , Johnson Glass 13001068Mexiku 3rd grade 04310109 Hiin Rahit Niichi, IQ/Kuku 1 Ko IJ-00001127 Crocodile Scale-lo 10 10 0 1 0 17 Lu = XL + 7 3 2 2 0 2 6 1 Lag Weed 0000-86 w >ζ−−10−−−− Numu, Scruff Glass 10 10 10 9 10 10 9 Suke, Hika 0311B86 Tropicano and Kuju 0400999 Key mouth, Wasuke-0300100 Compound Alfalfa 0200101 Inubi x O10 0 10 10 10, ζ-Mini H-Targlass 2 9 9101010 9 butto 1 nofusigcal glass 01000997 fee Predovi/Dweed 0000100 Agulhas 0910994 Jiyoung Glass 0200321 Mehishiba 16009B Fu Binted Heening Gukori-0000012,,K-100-100 zk2L/-7o 0 0 0 1 2 0 y-, y, (to 0-0 0 7 2 6, lean route >=-10----- Smooth Craft Glass 3107298 4 pieces. '-Jl-' 3 l ” 7 7 Tropicalk, N, 0000689 Key, 1 piece-0200100 Copy and translation of corrected sound) Submission form (Article 184-8 of the Patent Law) March 1, 8, 1992 D lab

Claims (45)

[Claims] 1. ▲There are mathematical formulas, chemical formulas, tables, etc.▼I; ▲There are mathematical formulas, chemical formulas, tables, etc.▼II ;▲There are mathematical formulas, chemical formulas, tables, etc.▼III;▲There are mathematical formulas, chemical formulas, tables, etc. ▼IV;▲There are mathematical formulas, chemical formulas, tables, etc.▼V;▲There are mathematical formulas, chemical formulas, tables, etc. ▼VI;▲There are mathematical formulas, chemical formulas, tables, etc.▼VII;▲There are mathematical formulas, chemical formulas, tables, etc. There is ▼VIII; [In the formula, X and Y are independently H or C(R3)(R4)OR5, and Z is C(R3 )(R4)OR5, R1 is H or linear C1-C3 alkyl, R2 is H, C1-C6 alkyl, C2-C4 alkenyl, C2-C4 alkynyl , phenyl, or Ph, OH, CN, OR6, SO2R6, PhSO2, N3 , C1-C4 alkyl substituted by CO2R8 or CO2H, R3, R4, R9 and R10 are independently H, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, or OCH3 or OCH2CH3 C1-C3 alkyl substituted with C1-C3 alkyl, R5 is C1-C3 alkyl, C2- C4 alkenyl, C3-C4 alkynyl, benzyl, or OR8, OCF3 is substituted C1-C4 alkyl, R8 is C1-C3 alkyl; Q is WCH2 or ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ and W is optionally F, Cl, Br, C1-C3 alkyl, C1-C3 alkoxy, OH , CN, C1-C3 haloalkyl, C1-C3 haloalkoxy, C1-C3 alk 1 selected from kylthio, C2-C4 alkenyl and C2-C4 alkynyl - phenyl optionally substituted with 3 substituents, or W is such that each ring is arbitrarily selected from F, Cl, Br, CH3 and OCH3. 0-2 nitrogen, 0-2 oxygen or or a 5- or 6-membered heterocyclic ring containing 0-2 sulfurs, Z1 is CH2, NRa, O, S or forms a double bond with adjacent carbons can, Ra is H or C1-C3 alkyl, R6 is H, halogen, R8, OR8 , SR8 or CN, and R7 is H, F, Cl, CH3, OCH3, OH or is OR8, q1 is 0, 1 or 2, and q is 0, 1 or 2, However, as a condition, 1) At least one of X and Y is C(R3)(R4)OR5, and 2) R3 , R4, R9 and R10 each contain up to 4 carbon atoms; 3) In formula II, if R1 is H, then X is C(R3)(R4)OR5 And Y is H, 4) the sum of q and q1 is 0, 1 or 2, and 5) the sum of q and q1 If the total is 0, then Z1 is CH2] Compounds of the formula selected from the group consisting of and their stereoisomers. 2. 1-2 W arbitrarily selected from F, C1, Br, CH3 and OCH3 is phenyl optionally substituted with a substituent, or W is each The ring optionally contains 1-2 moieties selected from F, Cl, Br, CH3 or OCH3 Tetrahydropyran, tetrahydrofuran, and nitrogen which may be substituted with substituents ofophene, isoxazole, pyridine or pyrazine; Q is ▲There are mathematical formulas, chemical formulas, tables, etc.▼Q-1, ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Q-2, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼Q-3, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼Q-4, ▲There are mathematical formulas, chemical formulas, tables, etc.▼Q-5, ▲Mathematical formulas, chemical formulas, There are tables, etc. ▼Q-6, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼Q-7, ▲ Mathematical formulas, There are chemical formulas, tables, etc.▼Q-8, ▲There are mathematical formulas, chemical formulas, tables, etc.▼Q-9, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼Q-10, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼Q-11, ▲There are mathematical formulas, chemical formulas, tables, etc. ▼Q-12, ▲Mathematical formulas, chemical formulas, tables, etc. There are ▼Q-13, ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼Q-14 or ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼Q-15: Ra is H or C1-C3 alkyl, and R5 is other than benzyl, Formula I, II, III, 1V, V, VI, VII, or VII according to claim 1 Compound I. 3. R2 is H, C1-C3 alkyl, C2-C3 alkenyl or C2-C3 a Luquinyl, A compound according to claim 2. 4. R3 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkyl Luquinyl, R4 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkyl Nil, R5 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkyl Nil, R9 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkyl Nil, R10 is H, C1-C3 alkyl, C3-C4 alkenyl or C3-C4 alkyl is quinyl, A compound according to claim 3. 5. Claim 4, wherein Q is Q-1, Q-3, Q-6, Q-7 or Q-15. Compounds listed. 6. 6. A compound according to claim 5, wherein the compound is of formula I. 7. 6. A compound according to claim 5, wherein the compound is of formula II. 8. 6. A compound according to claim 5, wherein the compound is of formula III. 9. 6. A compound according to claim 5, wherein the compound is of formula IV. 10. 6. A compound according to claim 5, wherein the compound is of formula V. 11. 6. A compound according to claim 5, wherein the compound is of formula VI. 12. 6. A compound according to claim 5, wherein the compound is of formula VII. 13. 6. A compound according to claim 5, wherein the compound is of formula VIII. 14.2-(1-ethyl-1-methoxypropyl)-6-(phenylmethoxy) -7-oxabicyclo[2.2.1]heptane, (2-exo, 6-exo) 7. The compound of claim 6, which is. 15.2-(ethoxymethyl)-5-methyl-4-(phenylmethoxy)-6- Oxabicyclo[3.2.1]octane, (2-endo, 4-endo), A compound according to claim 8. 16. an effective amount of a compound of claim 1 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 17. an effective amount of a compound of claim 2 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 18. an effective amount of a compound of claim 3 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 19. an effective amount of a compound of claim 4 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 20. an effective amount of a compound of claim 5 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 21. an effective amount of a compound of claim 6 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 22. an effective amount of a compound of claim 7 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 23. an effective amount of a compound of claim 8 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 24. an effective amount of a compound of claim 9 and at least one surfactant, a solid or consists of a liquid diluent, agriculturally suitable for regulating undesirable plant growth. composition. 25. an effective amount of the compound of claim 10 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 26. an effective amount of the compound of claim 11 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 27. an effective amount of the compound of claim 12 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 28. an effective amount of the compound of claim 13 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 29. an effective amount of the compound of claim 14 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 30. an effective amount of the compound of claim 15 and at least one surfactant, solid or Agriculturally suitable for controlling undesirable plant growth, consisting of composition. 31. from applying an effective amount of the compound of claim 1 to the site to be protected. methods of regulating undesirable plant growth. 32. from applying an effective amount of the compound of claim 2 to the site to be protected. methods of regulating undesirable plant growth. 33. from applying an effective amount of the compound of claim 3 to the site to be protected. methods of regulating undesirable plant growth. 34. from applying an effective amount of the compound of claim 4 to the site to be protected. methods of regulating undesirable plant growth. 35. from applying an effective amount of the compound of claim 5 to the site to be protected. methods of regulating undesirable plant growth. 36. from applying an effective amount of the compound of claim 6 to the site to be protected. methods of regulating undesirable plant growth. 37. from applying an effective amount of the compound of claim 7 to the site to be protected. methods of regulating undesirable plant growth. 38. from applying an effective amount of the compound of claim 8 to the site to be protected. methods of regulating undesirable plant growth. 39. from applying an effective amount of the compound of claim 9 to the site to be protected. methods of regulating undesirable plant growth. 40. From applying an effective amount of the compound of claim 10 to the area to be protected. How to control unwanted plant growth. 41. From applying an effective amount of the compound of claim 11 to the area to be protected. How to control unwanted plant growth. 42. From applying an effective amount of the compound of claim 12 to the area to be protected. How to control unwanted plant growth. 43. From applying an effective amount of the compound of claim 13 to the area to be protected. How to control unwanted plant growth. 44. From applying an effective amount of the compound of claim 14 to the site to be protected. How to control unwanted plant growth. 45. From applying an effective amount of the compound of claim 15 to the area to be protected. How to control unwanted plant growth.